Depsipeptides and cyclodepsipeptides are analogues of the corresponding peptides in which one or more amide groups are replaced by ester functions. Reports of crystal structures of linear depsipeptides are rare. The crystal structures and conformational analyses of four depsipeptides with an alternating sequence of an α,α-disubstituted α-amino acid and an α-hydroxy acid are reported. The molecules in the linear hexadepsipeptide amide in (
S)-Pms-Acp-(
S)-Pms-Acp-(
S)-Pms-Acp-NMe
2 acetonitrile solvate, C
47H
58N
4O
9·C
2H
3N, (
3b), as well as in the related linear tetradepsipeptide amide (
S)-Pms-Aib-(
S)-Pms-Aib-NMe
2, C
28H
37N
3O
6, (
5a), the diastereoisomeric mixture (
S,
R)-Pms-Acp-(
R,
S)-Pms-Acp-NMe
2/(
R,
S)-Pms-Acp-(
R,
S)-Pms-Acp-NMe
2 (1:1), C
32H
41N
3O
6, (
5b), and (
R,
S)-Mns-Acp-(
S,
R)-Mns-Acp-NMe
2, C
30H
37N
3O
6, (
5c) (Pms is phenyllactic acid, Acp is 1-aminocyclopentanecarboxylic acid and Mns is mandelic acid), generally adopt a β-turn conformation in the solid state, which is stabilized by intramolecular N—H
O hydrogen bonds. Whereas β-turns of type I (or I′) are formed in the cases of (
3b), (
5a) and (
5b), which contain phenyllactic acid, the torsion angles for (
5c), which incorporates mandelic acid, indicate a β-turn in between type I and type III. Intermolecular N—H
O and O—H
O hydrogen bonds link the molecules of (
3a) and (
5b) into extended chains, and those of (
5a) and (
5c) into two-dimensional networks.
Supporting information
CCDC references: 1968879; 1968878; 1968877; 1968876
For all structures, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
(
S)-Pms-Acp-(
S)-Pms-Acp-(
S)-Pms-Acp-NMe
2 (3b)
top
Crystal data top
C47H58N4O9·C2H3N | F(000) = 924 |
Mr = 864.02 | Dx = 1.226 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.645 (3) Å | Cell parameters from 20 reflections |
b = 19.161 (9) Å | θ = 10.0–12.5° |
c = 11.503 (3) Å | µ = 0.09 mm−1 |
β = 93.75 (2)° | T = 173 K |
V = 2341.5 (15) Å3 | Prism, colourless |
Z = 2 | 0.48 × 0.33 × 0.23 mm |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.066 |
Radiation source: Rigaku RU200 rotating anode generator | θmax = 27.5°, θmin = 2.5° |
Graphite monochromator | h = 0→13 |
ω–2θ scans | k = 0→24 |
5821 measured reflections | l = −14→14 |
5527 independent reflections | 3 standard reflections every 150 reflections |
3617 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0906P)2 + 3.1019P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.075 | (Δ/σ)max < 0.001 |
wR(F2) = 0.218 | Δρmax = 0.36 e Å−3 |
S = 1.04 | Δρmin = −0.28 e Å−3 |
5527 reflections | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
632 parameters | Extinction coefficient: 0.009 (2) |
229 restraints | Absolute structure: No quotients, so Flack parameter determined by classical intensity fit |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (2) |
Hydrogen site location: inferred from neighbouring sites | |
Special details top
Experimental. Solvent used: MeCN |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The asymmetric unit contains one molecule of the peptide and one molecule of
MeCN. Two five-membered rings and the terminal -NMe2 group are disordered.
Two sets of positions were defined for two of the -CH2- groups in two of the
five-membered rings and for the -NMe2 methyl groups. The site occupation
factors of the major conformations of these groups refined to 0.597 (18),
0.59 (2) and 0.880 (18), respectively. Similarity restraints were applied
to the chemically equivalent bond lengths and angles involving all
disordered C-atoms, while neighbouring atoms within and between each
conformation of the disordered groups were restrained to have similar
atomic displacement parameters. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O7 | 0.8591 (4) | 0.5444 (3) | 0.7255 (3) | 0.0263 (9) | |
O13 | 0.9280 (4) | 0.6485 (3) | 0.3926 (3) | 0.0288 (9) | |
O19 | 0.7833 (5) | 0.5572 (4) | 0.0570 (4) | 0.0494 (14) | |
H19 | 0.7232 | 0.5592 | 0.0060 | 0.074* | |
O27 | 0.8268 (4) | 0.5100 (3) | 0.3529 (3) | 0.0351 (11) | |
O32 | 1.0631 (4) | 0.5925 (3) | 0.5188 (3) | 0.0358 (11) | |
O40 | 0.7911 (4) | 0.6893 (3) | 0.6611 (3) | 0.0332 (10) | |
O45 | 0.6831 (4) | 0.5534 (3) | 0.8246 (4) | 0.0451 (13) | |
O53 | 1.0616 (4) | 0.5672 (3) | 0.9855 (3) | 0.0384 (11) | |
O58 | 1.2172 (5) | 0.7160 (4) | 1.0466 (4) | 0.0549 (15) | |
N1 | 1.2599 (6) | 0.6696 (5) | 0.8749 (5) | 0.068 (2) | |
N4 | 0.9841 (5) | 0.6441 (3) | 0.8501 (4) | 0.0329 (12) | |
H4 | 0.9416 | 0.6493 | 0.7825 | 0.040* | |
N10 | 0.7488 (4) | 0.6005 (3) | 0.5350 (4) | 0.0290 (11) | |
H10 | 0.7591 | 0.5829 | 0.4656 | 0.035* | |
N16 | 0.9577 (5) | 0.5538 (3) | 0.2256 (4) | 0.0297 (11) | |
H16 | 0.9681 | 0.5658 | 0.1530 | 0.036* | |
C2 | 1.1778 (8) | 0.6977 (5) | 0.9482 (6) | 0.050 (2) | |
C3 | 1.0395 (7) | 0.7056 (4) | 0.9112 (6) | 0.0419 (18) | |
C5 | 0.9978 (6) | 0.5811 (4) | 0.8964 (5) | 0.0303 (14) | |
C6 | 0.9344 (5) | 0.5204 (4) | 0.8268 (5) | 0.0262 (13) | |
H6 | 0.8805 | 0.4931 | 0.8784 | 0.031* | |
C8 | 0.7356 (6) | 0.5559 (4) | 0.7345 (5) | 0.0316 (14) | |
C9 | 0.6667 (5) | 0.5644 (4) | 0.6146 (5) | 0.0300 (13) | |
C11 | 0.8073 (6) | 0.6595 (4) | 0.5681 (5) | 0.0313 (14) | |
C12 | 0.8925 (6) | 0.6941 (4) | 0.4841 (5) | 0.0322 (14) | |
H12 | 0.9711 | 0.7092 | 0.5295 | 0.039* | |
C14 | 1.0192 (5) | 0.6003 (4) | 0.4211 (5) | 0.0279 (13) | |
C15 | 1.0631 (5) | 0.5627 (4) | 0.3139 (5) | 0.0260 (12) | |
C17 | 0.8484 (6) | 0.5284 (4) | 0.2525 (5) | 0.0290 (13) | |
C18 | 0.7437 (6) | 0.5220 (4) | 0.1568 (5) | 0.0336 (15) | |
H18 | 0.6676 | 0.5464 | 0.1831 | 0.040* | |
C20 | 0.7098 (7) | 0.4457 (4) | 0.1344 (7) | 0.0454 (18) | |
H201 | 0.7849 | 0.4210 | 0.1089 | 0.055* | |
H202 | 0.6872 | 0.4243 | 0.2085 | 0.055* | |
C21 | 0.6026 (7) | 0.4351 (4) | 0.0442 (6) | 0.0411 (16) | |
C22 | 0.6134 (9) | 0.3935 (6) | −0.0518 (8) | 0.062 (2) | |
H22 | 0.6914 | 0.3709 | −0.0619 | 0.075* | |
C23 | 0.5132 (9) | 0.3833 (6) | −0.1353 (8) | 0.071 (3) | |
H23 | 0.5231 | 0.3534 | −0.2000 | 0.085* | |
C24 | 0.4015 (9) | 0.4164 (6) | −0.1231 (8) | 0.066 (3) | |
H24 | 0.3333 | 0.4109 | −0.1799 | 0.079* | |
C25 | 0.3895 (8) | 0.4575 (6) | −0.0282 (8) | 0.067 (3) | |
H25 | 0.3107 | 0.4791 | −0.0178 | 0.080* | |
C26 | 0.4875 (7) | 0.4690 (6) | 0.0530 (7) | 0.061 (3) | |
H26 | 0.4769 | 0.5002 | 0.1158 | 0.073* | |
C28 | 1.1662 (6) | 0.6094 (4) | 0.2632 (5) | 0.0301 (14) | |
H281 | 1.1296 | 0.6385 | 0.1983 | 0.036* | |
H282 | 1.2053 | 0.6404 | 0.3241 | 0.036* | |
C29 | 1.2641 (6) | 0.5580 (4) | 0.2192 (6) | 0.0383 (15) | |
H291 | 1.2753 | 0.5658 | 0.1355 | 0.046* | |
H292 | 1.3464 | 0.5642 | 0.2632 | 0.046* | |
C30 | 1.2121 (7) | 0.4844 (4) | 0.2391 (6) | 0.0425 (17) | |
H301 | 1.1620 | 0.4676 | 0.1691 | 0.051* | |
H302 | 1.2812 | 0.4510 | 0.2585 | 0.051* | |
C31 | 1.1294 (6) | 0.4935 (4) | 0.3414 (6) | 0.0334 (14) | |
H311 | 1.0681 | 0.4549 | 0.3450 | 0.040* | |
H312 | 1.1808 | 0.4960 | 0.4161 | 0.040* | |
C33 | 0.8301 (6) | 0.7593 (4) | 0.4276 (6) | 0.0366 (15) | |
H331 | 0.8140 | 0.7937 | 0.4890 | 0.044* | |
H332 | 0.8882 | 0.7808 | 0.3742 | 0.044* | |
C34 | 0.7080 (6) | 0.7414 (4) | 0.3609 (5) | 0.0318 (14) | |
C35 | 0.5952 (7) | 0.7561 (5) | 0.4082 (7) | 0.050 (2) | |
H35 | 0.5959 | 0.7782 | 0.4822 | 0.060* | |
C36 | 0.4816 (8) | 0.7395 (6) | 0.3506 (8) | 0.064 (3) | |
H36 | 0.4047 | 0.7495 | 0.3847 | 0.077* | |
C37 | 0.4813 (8) | 0.7072 (5) | 0.2389 (9) | 0.066 (3) | |
H37 | 0.4041 | 0.6943 | 0.1987 | 0.079* | |
C38 | 0.5913 (8) | 0.6952 (5) | 0.1909 (8) | 0.063 (3) | |
H38 | 0.5910 | 0.6745 | 0.1158 | 0.076* | |
C39 | 0.7061 (7) | 0.7128 (5) | 0.2501 (6) | 0.0464 (18) | |
H39 | 0.7828 | 0.7051 | 0.2143 | 0.056* | |
C41 | 0.5396 (6) | 0.6037 (5) | 0.6198 (6) | 0.0446 (15) | |
H411 | 0.5093 | 0.6010 | 0.6992 | 0.054* | 0.597 (18) |
H412 | 0.5499 | 0.6534 | 0.5993 | 0.054* | 0.597 (18) |
H413 | 0.5505 | 0.6549 | 0.6163 | 0.054* | 0.403 (18) |
H414 | 0.4956 | 0.5912 | 0.6901 | 0.054* | 0.403 (18) |
C42A | 0.4448 (10) | 0.5678 (8) | 0.5311 (12) | 0.0503 (19) | 0.597 (18) |
H421 | 0.4157 | 0.6011 | 0.4693 | 0.060* | 0.597 (18) |
H422 | 0.3707 | 0.5509 | 0.5705 | 0.060* | 0.597 (18) |
C43A | 0.5150 (10) | 0.5057 (7) | 0.4779 (11) | 0.0478 (18) | 0.597 (18) |
H431 | 0.4600 | 0.4641 | 0.4703 | 0.057* | 0.597 (18) |
H432 | 0.5431 | 0.5180 | 0.4001 | 0.057* | 0.597 (18) |
C42B | 0.4712 (19) | 0.5743 (8) | 0.5069 (11) | 0.0474 (19) | 0.403 (18) |
H423 | 0.5131 | 0.5889 | 0.4364 | 0.057* | 0.403 (18) |
H424 | 0.3816 | 0.5884 | 0.4993 | 0.057* | 0.403 (18) |
C43B | 0.4864 (8) | 0.4949 (9) | 0.531 (2) | 0.0487 (19) | 0.403 (18) |
H433 | 0.4357 | 0.4793 | 0.5949 | 0.058* | 0.403 (18) |
H434 | 0.4640 | 0.4668 | 0.4600 | 0.058* | 0.403 (18) |
C44 | 0.6296 (6) | 0.4919 (5) | 0.5652 (6) | 0.0428 (15) | |
H441 | 0.6063 | 0.4602 | 0.6282 | 0.051* | 0.597 (18) |
H442 | 0.7000 | 0.4709 | 0.5252 | 0.051* | 0.597 (18) |
H443 | 0.6478 | 0.4554 | 0.6248 | 0.051* | 0.403 (18) |
H444 | 0.6773 | 0.4813 | 0.4964 | 0.051* | 0.403 (18) |
C46 | 1.0330 (6) | 0.4724 (4) | 0.7782 (6) | 0.0347 (15) | |
H461 | 1.0863 | 0.4995 | 0.7272 | 0.042* | |
H462 | 1.0879 | 0.4531 | 0.8431 | 0.042* | |
C47 | 0.9702 (5) | 0.4133 (4) | 0.7094 (5) | 0.0278 (13) | |
C48 | 0.9559 (6) | 0.4160 (4) | 0.5875 (5) | 0.0352 (15) | |
H48 | 0.9893 | 0.4544 | 0.5474 | 0.042* | |
C49 | 0.8936 (7) | 0.3632 (4) | 0.5247 (6) | 0.0394 (16) | |
H49 | 0.8865 | 0.3649 | 0.4420 | 0.047* | |
C50 | 0.8422 (7) | 0.3083 (4) | 0.5820 (6) | 0.0422 (17) | |
H50 | 0.7986 | 0.2725 | 0.5387 | 0.051* | |
C51 | 0.8535 (7) | 0.3048 (4) | 0.7009 (6) | 0.0426 (17) | |
H51 | 0.8184 | 0.2665 | 0.7399 | 0.051* | |
C52 | 0.9163 (6) | 0.3572 (4) | 0.7650 (5) | 0.0340 (14) | |
H52 | 0.9225 | 0.3548 | 0.8476 | 0.041* | |
C54 | 1.0241 (9) | 0.7699 (5) | 0.8276 (7) | 0.067 (2) | |
H541 | 1.1061 | 0.7924 | 0.8160 | 0.080* | 0.59 (2) |
H542 | 0.9833 | 0.7567 | 0.7510 | 0.080* | 0.59 (2) |
H543 | 1.0968 | 0.8019 | 0.8401 | 0.080* | 0.41 (2) |
H544 | 1.0187 | 0.7545 | 0.7453 | 0.080* | 0.41 (2) |
C55A | 0.9380 (16) | 0.8178 (7) | 0.8965 (16) | 0.070 (2) | 0.59 (2) |
H551 | 0.8896 | 0.8507 | 0.8445 | 0.085* | 0.59 (2) |
H552 | 0.9867 | 0.8443 | 0.9580 | 0.085* | 0.59 (2) |
C56A | 0.8513 (12) | 0.7625 (8) | 0.9489 (16) | 0.068 (2) | 0.59 (2) |
H561 | 0.7917 | 0.7832 | 1.0018 | 0.081* | 0.59 (2) |
H562 | 0.8051 | 0.7339 | 0.8885 | 0.081* | 0.59 (2) |
C55B | 0.9008 (17) | 0.8070 (14) | 0.8570 (19) | 0.069 (2) | 0.41 (2) |
H553 | 0.8325 | 0.7960 | 0.7973 | 0.083* | 0.41 (2) |
H554 | 0.9133 | 0.8582 | 0.8587 | 0.083* | 0.41 (2) |
C56B | 0.866 (2) | 0.7807 (12) | 0.9782 (17) | 0.068 (2) | 0.41 (2) |
H563 | 0.8719 | 0.8193 | 1.0356 | 0.082* | 0.41 (2) |
H564 | 0.7784 | 0.7626 | 0.9737 | 0.082* | 0.41 (2) |
C57 | 0.9598 (8) | 0.7219 (5) | 1.0151 (7) | 0.0610 (19) | |
H571 | 1.0061 | 0.7512 | 1.0745 | 0.073* | 0.59 (2) |
H572 | 0.9295 | 0.6789 | 1.0520 | 0.073* | 0.59 (2) |
H573 | 1.0150 | 0.7370 | 1.0830 | 0.073* | 0.41 (2) |
H574 | 0.9135 | 0.6796 | 1.0374 | 0.073* | 0.41 (2) |
C59A | 1.2331 (11) | 0.6496 (9) | 0.7517 (6) | 0.067 (3) | 0.880 (18) |
H591 | 1.2298 | 0.5987 | 0.7454 | 0.100* | 0.880 (18) |
H592 | 1.2997 | 0.6676 | 0.7050 | 0.100* | 0.880 (18) |
H593 | 1.1520 | 0.6694 | 0.7231 | 0.100* | 0.880 (18) |
C60A | 1.3921 (8) | 0.6580 (8) | 0.9182 (8) | 0.072 (3) | 0.880 (18) |
H601 | 1.4372 | 0.7026 | 0.9209 | 0.107* | 0.880 (18) |
H602 | 1.4325 | 0.6258 | 0.8658 | 0.107* | 0.880 (18) |
H603 | 1.3942 | 0.6378 | 0.9966 | 0.107* | 0.880 (18) |
C59B | 1.195 (7) | 0.673 (7) | 0.758 (3) | 0.068 (3) | 0.120 (18) |
H594 | 1.1354 | 0.6344 | 0.7474 | 0.102* | 0.120 (18) |
H595 | 1.2567 | 0.6706 | 0.6985 | 0.102* | 0.120 (18) |
H596 | 1.1487 | 0.7176 | 0.7493 | 0.102* | 0.120 (18) |
C60B | 1.363 (6) | 0.717 (4) | 0.915 (6) | 0.070 (3) | 0.120 (18) |
H604 | 1.3276 | 0.7625 | 0.9356 | 0.105* | 0.120 (18) |
H605 | 1.4201 | 0.7238 | 0.8523 | 0.105* | 0.120 (18) |
H606 | 1.4096 | 0.6972 | 0.9832 | 0.105* | 0.120 (18) |
N63 | 0.3687 (16) | 0.8031 (9) | 0.6648 (12) | 0.150 (6) | |
C61 | 0.5884 (13) | 0.8022 (9) | 0.7855 (15) | 0.127 (5) | |
H611 | 0.5770 | 0.8187 | 0.8647 | 0.190* | |
H612 | 0.6497 | 0.8320 | 0.7493 | 0.190* | |
H613 | 0.6192 | 0.7540 | 0.7884 | 0.190* | |
C62 | 0.4663 (13) | 0.8050 (7) | 0.7159 (12) | 0.095 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O7 | 0.025 (2) | 0.034 (3) | 0.0193 (18) | 0.0008 (18) | 0.0000 (15) | 0.0000 (17) |
O13 | 0.030 (2) | 0.036 (3) | 0.0197 (19) | 0.001 (2) | −0.0024 (15) | −0.0010 (18) |
O19 | 0.051 (3) | 0.069 (4) | 0.028 (2) | −0.023 (3) | −0.002 (2) | 0.010 (3) |
O27 | 0.042 (3) | 0.043 (3) | 0.020 (2) | −0.001 (2) | 0.0004 (18) | 0.0017 (19) |
O32 | 0.037 (2) | 0.047 (3) | 0.022 (2) | 0.008 (2) | −0.0031 (17) | −0.004 (2) |
O40 | 0.038 (2) | 0.035 (3) | 0.026 (2) | 0.007 (2) | −0.0006 (18) | −0.0058 (19) |
O45 | 0.036 (2) | 0.079 (4) | 0.021 (2) | −0.002 (3) | 0.0027 (17) | −0.001 (2) |
O53 | 0.035 (2) | 0.055 (3) | 0.024 (2) | −0.007 (2) | −0.0065 (18) | −0.002 (2) |
O58 | 0.057 (3) | 0.075 (4) | 0.031 (2) | −0.034 (3) | −0.011 (2) | −0.002 (3) |
N1 | 0.051 (3) | 0.119 (6) | 0.035 (3) | −0.027 (4) | 0.008 (2) | −0.009 (3) |
N4 | 0.033 (3) | 0.040 (3) | 0.024 (2) | −0.016 (2) | −0.007 (2) | −0.001 (2) |
N10 | 0.028 (3) | 0.041 (3) | 0.017 (2) | 0.002 (2) | −0.0002 (18) | −0.002 (2) |
N16 | 0.034 (3) | 0.040 (3) | 0.015 (2) | −0.001 (2) | −0.0002 (18) | 0.000 (2) |
C2 | 0.060 (5) | 0.058 (5) | 0.031 (3) | −0.039 (4) | −0.006 (3) | 0.001 (3) |
C3 | 0.066 (5) | 0.030 (4) | 0.029 (3) | −0.019 (3) | −0.010 (3) | 0.001 (3) |
C5 | 0.029 (3) | 0.039 (4) | 0.023 (3) | −0.006 (3) | 0.003 (2) | −0.002 (3) |
C6 | 0.021 (3) | 0.039 (4) | 0.019 (3) | −0.008 (3) | −0.003 (2) | 0.001 (2) |
C8 | 0.031 (3) | 0.044 (4) | 0.020 (3) | −0.003 (3) | 0.000 (2) | −0.004 (3) |
C9 | 0.029 (3) | 0.040 (4) | 0.020 (3) | −0.002 (3) | −0.003 (2) | 0.001 (3) |
C11 | 0.032 (3) | 0.036 (4) | 0.026 (3) | 0.006 (3) | 0.000 (2) | −0.001 (3) |
C12 | 0.032 (3) | 0.037 (4) | 0.027 (3) | 0.001 (3) | 0.000 (2) | −0.007 (3) |
C14 | 0.026 (3) | 0.033 (3) | 0.024 (3) | −0.003 (3) | 0.000 (2) | 0.001 (3) |
C15 | 0.026 (3) | 0.030 (3) | 0.022 (3) | −0.002 (3) | 0.000 (2) | 0.005 (2) |
C17 | 0.035 (3) | 0.024 (3) | 0.028 (3) | −0.003 (3) | 0.003 (2) | −0.002 (2) |
C18 | 0.036 (3) | 0.045 (4) | 0.021 (3) | −0.009 (3) | 0.009 (2) | 0.000 (3) |
C20 | 0.049 (4) | 0.040 (4) | 0.046 (4) | −0.003 (3) | −0.001 (3) | −0.009 (3) |
C21 | 0.043 (4) | 0.032 (4) | 0.047 (4) | −0.009 (3) | 0.000 (3) | −0.006 (3) |
C22 | 0.062 (5) | 0.067 (6) | 0.056 (5) | 0.006 (5) | −0.003 (4) | −0.026 (5) |
C23 | 0.073 (6) | 0.075 (7) | 0.064 (6) | −0.012 (5) | −0.003 (5) | −0.045 (5) |
C24 | 0.057 (5) | 0.073 (7) | 0.064 (6) | −0.019 (5) | −0.016 (4) | −0.022 (5) |
C25 | 0.040 (4) | 0.089 (8) | 0.071 (6) | −0.005 (5) | −0.001 (4) | −0.034 (5) |
C26 | 0.041 (4) | 0.084 (7) | 0.059 (5) | −0.005 (4) | 0.005 (4) | −0.038 (5) |
C28 | 0.034 (3) | 0.032 (3) | 0.025 (3) | −0.011 (3) | 0.001 (2) | 0.001 (3) |
C29 | 0.032 (3) | 0.045 (4) | 0.038 (3) | −0.002 (3) | 0.008 (3) | 0.002 (3) |
C30 | 0.047 (4) | 0.033 (4) | 0.049 (4) | 0.004 (3) | 0.013 (3) | 0.000 (3) |
C31 | 0.042 (4) | 0.024 (3) | 0.034 (3) | 0.001 (3) | −0.001 (3) | 0.002 (3) |
C33 | 0.036 (4) | 0.034 (4) | 0.039 (3) | −0.005 (3) | 0.000 (3) | 0.001 (3) |
C34 | 0.039 (3) | 0.030 (3) | 0.027 (3) | 0.003 (3) | 0.001 (2) | 0.012 (3) |
C35 | 0.044 (4) | 0.065 (6) | 0.041 (4) | 0.007 (4) | 0.005 (3) | 0.012 (4) |
C36 | 0.042 (4) | 0.081 (7) | 0.071 (6) | 0.012 (4) | 0.008 (4) | 0.033 (5) |
C37 | 0.045 (5) | 0.064 (6) | 0.084 (7) | −0.013 (4) | −0.026 (4) | 0.032 (5) |
C38 | 0.059 (5) | 0.065 (6) | 0.063 (5) | 0.020 (5) | −0.021 (4) | −0.008 (5) |
C39 | 0.044 (4) | 0.056 (5) | 0.038 (4) | 0.008 (4) | −0.005 (3) | −0.004 (3) |
C41 | 0.031 (3) | 0.068 (4) | 0.033 (3) | 0.000 (3) | −0.003 (2) | −0.004 (3) |
C42A | 0.035 (3) | 0.071 (4) | 0.044 (3) | −0.003 (3) | −0.003 (3) | −0.003 (3) |
C43A | 0.035 (3) | 0.070 (4) | 0.038 (3) | −0.006 (3) | −0.001 (3) | −0.004 (3) |
C42B | 0.032 (3) | 0.070 (4) | 0.040 (4) | −0.005 (3) | −0.001 (3) | −0.001 (3) |
C43B | 0.036 (3) | 0.069 (4) | 0.040 (4) | −0.007 (3) | −0.002 (3) | −0.004 (3) |
C44 | 0.035 (3) | 0.063 (4) | 0.030 (3) | −0.013 (3) | −0.003 (2) | −0.004 (3) |
C46 | 0.028 (3) | 0.042 (4) | 0.033 (3) | 0.002 (3) | −0.001 (3) | −0.002 (3) |
C47 | 0.026 (3) | 0.030 (3) | 0.027 (3) | 0.004 (2) | 0.000 (2) | −0.003 (3) |
C48 | 0.045 (4) | 0.029 (4) | 0.031 (3) | 0.004 (3) | 0.003 (3) | 0.005 (3) |
C49 | 0.044 (4) | 0.038 (4) | 0.035 (3) | 0.007 (3) | −0.004 (3) | 0.000 (3) |
C50 | 0.048 (4) | 0.038 (4) | 0.041 (4) | −0.005 (3) | −0.004 (3) | −0.006 (3) |
C51 | 0.054 (4) | 0.035 (4) | 0.040 (4) | −0.004 (3) | 0.008 (3) | 0.006 (3) |
C52 | 0.040 (3) | 0.037 (4) | 0.025 (3) | 0.010 (3) | 0.002 (3) | 0.006 (3) |
C54 | 0.094 (5) | 0.051 (4) | 0.052 (4) | −0.012 (4) | −0.023 (4) | −0.002 (3) |
C55A | 0.096 (5) | 0.053 (4) | 0.059 (4) | −0.002 (4) | −0.022 (4) | −0.004 (4) |
C56A | 0.094 (5) | 0.050 (4) | 0.056 (4) | 0.001 (4) | −0.018 (4) | −0.011 (3) |
C55B | 0.096 (5) | 0.051 (4) | 0.055 (4) | −0.004 (4) | −0.024 (4) | −0.006 (4) |
C56B | 0.093 (5) | 0.052 (4) | 0.056 (4) | −0.001 (4) | −0.020 (4) | −0.009 (4) |
C57 | 0.086 (5) | 0.046 (4) | 0.048 (4) | −0.001 (4) | −0.016 (3) | −0.012 (3) |
C59A | 0.051 (4) | 0.117 (7) | 0.034 (3) | −0.026 (4) | 0.012 (3) | −0.014 (4) |
C60A | 0.049 (4) | 0.123 (7) | 0.043 (4) | −0.022 (4) | 0.005 (3) | −0.007 (4) |
C59B | 0.052 (5) | 0.118 (7) | 0.035 (4) | −0.027 (5) | 0.011 (4) | −0.012 (5) |
C60B | 0.051 (5) | 0.121 (7) | 0.040 (4) | −0.025 (5) | 0.007 (4) | −0.008 (5) |
N63 | 0.169 (13) | 0.131 (12) | 0.140 (11) | 0.028 (11) | −0.071 (10) | −0.018 (10) |
C61 | 0.086 (9) | 0.100 (11) | 0.191 (16) | −0.005 (8) | −0.022 (10) | −0.027 (11) |
C62 | 0.098 (9) | 0.074 (8) | 0.111 (10) | 0.009 (7) | −0.012 (8) | −0.020 (7) |
Geometric parameters (Å, º) top
O7—C8 | 1.344 (7) | C37—H37 | 0.9500 |
O7—C6 | 1.445 (7) | C38—C39 | 1.401 (11) |
O13—C14 | 1.364 (7) | C38—H38 | 0.9500 |
O13—C12 | 1.438 (7) | C39—H39 | 0.9500 |
O19—C18 | 1.418 (7) | C41—C42A | 1.548 (6) |
O19—H19 | 0.8400 | C41—C42B | 1.552 (6) |
O27—C17 | 1.243 (7) | C41—H411 | 0.9900 |
O32—C14 | 1.198 (7) | C41—H412 | 0.9900 |
O40—C11 | 1.235 (7) | C41—H413 | 0.9900 |
O45—C8 | 1.210 (7) | C41—H414 | 0.9900 |
O53—C5 | 1.221 (7) | C42A—C43A | 1.552 (6) |
O58—C2 | 1.231 (8) | C42A—H421 | 0.9900 |
N1—C2 | 1.365 (11) | C42A—H422 | 0.9900 |
N1—C59A | 1.477 (7) | C43A—C44 | 1.551 (6) |
N1—C60B | 1.477 (8) | C43A—H431 | 0.9900 |
N1—C59B | 1.478 (8) | C43A—H432 | 0.9900 |
N1—C60A | 1.478 (8) | C42B—C43B | 1.553 (6) |
N4—C5 | 1.322 (9) | C42B—H423 | 0.9900 |
N4—C3 | 1.475 (8) | C42B—H424 | 0.9900 |
N4—H4 | 0.8800 | C43B—C44 | 1.551 (6) |
N10—C11 | 1.335 (9) | C43B—H433 | 0.9900 |
N10—C9 | 1.478 (8) | C43B—H434 | 0.9900 |
N10—H10 | 0.8800 | C44—H441 | 0.9900 |
N16—C17 | 1.317 (8) | C44—H442 | 0.9900 |
N16—C15 | 1.473 (7) | C44—H443 | 0.9900 |
N16—H16 | 0.8800 | C44—H444 | 0.9900 |
C2—C3 | 1.514 (11) | C46—C47 | 1.511 (9) |
C3—C57 | 1.542 (12) | C46—H461 | 0.9900 |
C3—C54 | 1.565 (11) | C46—H462 | 0.9900 |
C5—C6 | 1.542 (9) | C47—C52 | 1.393 (9) |
C6—C46 | 1.530 (9) | C47—C48 | 1.402 (8) |
C6—H6 | 1.0000 | C48—C49 | 1.387 (10) |
C8—C9 | 1.528 (8) | C48—H48 | 0.9500 |
C9—C44 | 1.542 (10) | C49—C50 | 1.374 (10) |
C9—C41 | 1.552 (9) | C49—H49 | 0.9500 |
C11—C12 | 1.520 (9) | C50—C51 | 1.367 (10) |
C12—C33 | 1.539 (10) | C50—H50 | 0.9500 |
C12—H12 | 1.0000 | C51—C52 | 1.391 (11) |
C14—C15 | 1.527 (8) | C51—H51 | 0.9500 |
C15—C31 | 1.525 (9) | C52—H52 | 0.9500 |
C15—C28 | 1.559 (8) | C54—C55B | 1.549 (6) |
C17—C18 | 1.520 (9) | C54—C55A | 1.551 (6) |
C18—C20 | 1.524 (10) | C54—H541 | 0.9900 |
C18—H18 | 1.0000 | C54—H542 | 0.9900 |
C20—C21 | 1.506 (10) | C54—H543 | 0.9900 |
C20—H201 | 0.9900 | C54—H544 | 0.9900 |
C20—H202 | 0.9900 | C55A—C56A | 1.553 (6) |
C21—C22 | 1.372 (11) | C55A—H551 | 0.9900 |
C21—C26 | 1.396 (11) | C55A—H552 | 0.9900 |
C22—C23 | 1.402 (12) | C56A—C57 | 1.551 (6) |
C22—H22 | 0.9500 | C56A—H561 | 0.9900 |
C23—C24 | 1.363 (14) | C56A—H562 | 0.9900 |
C23—H23 | 0.9500 | C55B—C56B | 1.551 (6) |
C24—C25 | 1.359 (12) | C55B—H553 | 0.9900 |
C24—H24 | 0.9500 | C55B—H554 | 0.9900 |
C25—C26 | 1.371 (12) | C56B—C57 | 1.550 (6) |
C25—H25 | 0.9500 | C56B—H563 | 0.9900 |
C26—H26 | 0.9500 | C56B—H564 | 0.9900 |
C28—C29 | 1.543 (9) | C57—H571 | 0.9900 |
C28—H281 | 0.9900 | C57—H572 | 0.9900 |
C28—H282 | 0.9900 | C57—H573 | 0.9900 |
C29—C30 | 1.537 (11) | C57—H574 | 0.9900 |
C29—H291 | 0.9900 | C59A—H591 | 0.9800 |
C29—H292 | 0.9900 | C59A—H592 | 0.9800 |
C30—C31 | 1.525 (9) | C59A—H593 | 0.9800 |
C30—H301 | 0.9900 | C60A—H601 | 0.9800 |
C30—H302 | 0.9900 | C60A—H602 | 0.9800 |
C31—H311 | 0.9900 | C60A—H603 | 0.9800 |
C31—H312 | 0.9900 | C59B—H594 | 0.9800 |
C33—C34 | 1.506 (9) | C59B—H595 | 0.9800 |
C33—H331 | 0.9900 | C59B—H596 | 0.9800 |
C33—H332 | 0.9900 | C60B—H604 | 0.9800 |
C34—C35 | 1.380 (10) | C60B—H605 | 0.9800 |
C34—C39 | 1.386 (10) | C60B—H606 | 0.9800 |
C35—C36 | 1.377 (12) | N63—C62 | 1.160 (16) |
C35—H35 | 0.9500 | C61—C62 | 1.482 (18) |
C36—C37 | 1.426 (15) | C61—H611 | 0.9800 |
C36—H36 | 0.9500 | C61—H612 | 0.9800 |
C37—C38 | 1.347 (13) | C61—H613 | 0.9800 |
| | | |
C8—O7—C6 | 118.9 (4) | C42A—C41—H412 | 110.3 |
C14—O13—C12 | 116.9 (4) | C9—C41—H412 | 110.3 |
C18—O19—H19 | 109.5 | H411—C41—H412 | 108.6 |
C2—N1—C59A | 127.1 (7) | C9—C41—H413 | 112.0 |
C2—N1—C60B | 93 (3) | C42B—C41—H413 | 112.0 |
C2—N1—C59B | 105 (4) | C9—C41—H414 | 112.0 |
C60B—N1—C59B | 123 (5) | C42B—C41—H414 | 112.0 |
C2—N1—C60A | 119.0 (7) | H413—C41—H414 | 109.7 |
C59A—N1—C60A | 113.9 (8) | C41—C42A—C43A | 106.9 (8) |
C5—N4—C3 | 120.4 (5) | C41—C42A—H421 | 110.3 |
C5—N4—H4 | 119.8 | C43A—C42A—H421 | 110.3 |
C3—N4—H4 | 119.8 | C41—C42A—H422 | 110.3 |
C11—N10—C9 | 120.2 (5) | C43A—C42A—H422 | 110.3 |
C11—N10—H10 | 119.9 | H421—C42A—H422 | 108.6 |
C9—N10—H10 | 119.9 | C44—C43A—C42A | 104.7 (8) |
C17—N16—C15 | 121.6 (5) | C44—C43A—H431 | 110.8 |
C17—N16—H16 | 119.2 | C42A—C43A—H431 | 110.8 |
C15—N16—H16 | 119.2 | C44—C43A—H432 | 110.8 |
O58—C2—N1 | 119.1 (7) | C42A—C43A—H432 | 110.8 |
O58—C2—C3 | 119.8 (8) | H431—C43A—H432 | 108.9 |
N1—C2—C3 | 121.1 (6) | C41—C42B—C43B | 99.8 (11) |
N4—C3—C2 | 113.9 (6) | C41—C42B—H423 | 111.8 |
N4—C3—C57 | 107.9 (6) | C43B—C42B—H423 | 111.8 |
C2—C3—C57 | 112.1 (6) | C41—C42B—H424 | 111.8 |
N4—C3—C54 | 108.3 (5) | C43B—C42B—H424 | 111.8 |
C2—C3—C54 | 108.2 (6) | H423—C42B—H424 | 109.5 |
C57—C3—C54 | 106.0 (7) | C44—C43B—C42B | 99.8 (12) |
O53—C5—N4 | 125.3 (6) | C44—C43B—H433 | 111.8 |
O53—C5—C6 | 118.1 (6) | C42B—C43B—H433 | 111.8 |
N4—C5—C6 | 116.5 (5) | C44—C43B—H434 | 111.8 |
O7—C6—C46 | 104.7 (4) | C42B—C43B—H434 | 111.8 |
O7—C6—C5 | 112.3 (5) | H433—C43B—H434 | 109.5 |
C46—C6—C5 | 110.9 (5) | C9—C44—C43B | 106.6 (9) |
O7—C6—H6 | 109.6 | C9—C44—C43A | 104.9 (7) |
C46—C6—H6 | 109.6 | C9—C44—H441 | 110.8 |
C5—C6—H6 | 109.6 | C43A—C44—H441 | 110.8 |
O45—C8—O7 | 124.6 (5) | C9—C44—H442 | 110.8 |
O45—C8—C9 | 123.8 (5) | C43A—C44—H442 | 110.8 |
O7—C8—C9 | 111.3 (5) | H441—C44—H442 | 108.8 |
N10—C9—C8 | 109.9 (5) | C9—C44—H443 | 110.4 |
N10—C9—C44 | 109.9 (5) | C43B—C44—H443 | 110.4 |
C8—C9—C44 | 109.4 (6) | C9—C44—H444 | 110.4 |
N10—C9—C41 | 110.5 (6) | C43B—C44—H444 | 110.4 |
C8—C9—C41 | 112.7 (5) | H443—C44—H444 | 108.6 |
C44—C9—C41 | 104.4 (5) | C47—C46—C6 | 110.6 (5) |
O40—C11—N10 | 123.4 (6) | C47—C46—H461 | 109.5 |
O40—C11—C12 | 118.1 (6) | C6—C46—H461 | 109.5 |
N10—C11—C12 | 118.4 (5) | C47—C46—H462 | 109.5 |
O13—C12—C11 | 113.4 (5) | C6—C46—H462 | 109.5 |
O13—C12—C33 | 108.1 (5) | H461—C46—H462 | 108.1 |
C11—C12—C33 | 111.3 (5) | C52—C47—C48 | 117.7 (6) |
O13—C12—H12 | 107.9 | C52—C47—C46 | 121.3 (5) |
C11—C12—H12 | 107.9 | C48—C47—C46 | 120.8 (6) |
C33—C12—H12 | 107.9 | C49—C48—C47 | 120.8 (6) |
O32—C14—O13 | 122.5 (6) | C49—C48—H48 | 119.6 |
O32—C14—C15 | 125.3 (6) | C47—C48—H48 | 119.6 |
O13—C14—C15 | 112.1 (5) | C50—C49—C48 | 120.0 (6) |
N16—C15—C31 | 111.4 (5) | C50—C49—H49 | 120.0 |
N16—C15—C14 | 110.6 (5) | C48—C49—H49 | 120.0 |
C31—C15—C14 | 113.9 (5) | C51—C50—C49 | 120.4 (7) |
N16—C15—C28 | 109.3 (5) | C51—C50—H50 | 119.8 |
C31—C15—C28 | 104.4 (5) | C49—C50—H50 | 119.8 |
C14—C15—C28 | 106.9 (5) | C50—C51—C52 | 120.2 (7) |
O27—C17—N16 | 122.9 (6) | C50—C51—H51 | 119.9 |
O27—C17—C18 | 118.6 (5) | C52—C51—H51 | 119.9 |
N16—C17—C18 | 118.5 (5) | C51—C52—C47 | 120.8 (6) |
O19—C18—C17 | 107.8 (5) | C51—C52—H52 | 119.6 |
O19—C18—C20 | 113.5 (6) | C47—C52—H52 | 119.6 |
C17—C18—C20 | 110.8 (6) | C55B—C54—C3 | 106.5 (10) |
O19—C18—H18 | 108.2 | C55A—C54—C3 | 101.2 (9) |
C17—C18—H18 | 108.2 | C55A—C54—H541 | 111.5 |
C20—C18—H18 | 108.2 | C3—C54—H541 | 111.5 |
C21—C20—C18 | 114.0 (6) | C55A—C54—H542 | 111.5 |
C21—C20—H201 | 108.8 | C3—C54—H542 | 111.5 |
C18—C20—H201 | 108.8 | H541—C54—H542 | 109.4 |
C21—C20—H202 | 108.8 | C55B—C54—H543 | 110.4 |
C18—C20—H202 | 108.8 | C3—C54—H543 | 110.4 |
H201—C20—H202 | 107.7 | C55B—C54—H544 | 110.4 |
C22—C21—C26 | 116.7 (7) | C3—C54—H544 | 110.4 |
C22—C21—C20 | 122.2 (7) | H543—C54—H544 | 108.6 |
C26—C21—C20 | 121.1 (7) | C54—C55A—C56A | 100.4 (11) |
C21—C22—C23 | 122.1 (8) | C54—C55A—H551 | 111.7 |
C21—C22—H22 | 118.9 | C56A—C55A—H551 | 111.7 |
C23—C22—H22 | 118.9 | C54—C55A—H552 | 111.7 |
C24—C23—C22 | 119.6 (8) | C56A—C55A—H552 | 111.7 |
C24—C23—H23 | 120.2 | H551—C55A—H552 | 109.5 |
C22—C23—H23 | 120.2 | C57—C56A—C55A | 95.2 (11) |
C25—C24—C23 | 118.7 (8) | C57—C56A—H561 | 112.7 |
C25—C24—H24 | 120.6 | C55A—C56A—H561 | 112.7 |
C23—C24—H24 | 120.6 | C57—C56A—H562 | 112.7 |
C24—C25—C26 | 122.2 (9) | C55A—C56A—H562 | 112.7 |
C24—C25—H25 | 118.9 | H561—C56A—H562 | 110.2 |
C26—C25—H25 | 118.9 | C54—C55B—C56B | 107.8 (13) |
C25—C26—C21 | 120.5 (8) | C54—C55B—H553 | 110.2 |
C25—C26—H26 | 119.7 | C56B—C55B—H553 | 110.2 |
C21—C26—H26 | 119.7 | C54—C55B—H554 | 110.2 |
C29—C28—C15 | 105.3 (5) | C56B—C55B—H554 | 110.2 |
C29—C28—H281 | 110.7 | H553—C55B—H554 | 108.5 |
C15—C28—H281 | 110.7 | C57—C56B—C55B | 107.0 (13) |
C29—C28—H282 | 110.7 | C57—C56B—H563 | 110.3 |
C15—C28—H282 | 110.7 | C55B—C56B—H563 | 110.3 |
H281—C28—H282 | 108.8 | C57—C56B—H564 | 110.3 |
C30—C29—C28 | 106.2 (5) | C55B—C56B—H564 | 110.3 |
C30—C29—H291 | 110.5 | H563—C56B—H564 | 108.6 |
C28—C29—H291 | 110.5 | C3—C57—C56B | 108.3 (9) |
C30—C29—H292 | 110.5 | C3—C57—C56A | 98.6 (9) |
C28—C29—H292 | 110.5 | C3—C57—H571 | 112.0 |
H291—C29—H292 | 108.7 | C56A—C57—H571 | 112.0 |
C31—C30—C29 | 104.0 (6) | C3—C57—H572 | 112.0 |
C31—C30—H301 | 111.0 | C56A—C57—H572 | 112.0 |
C29—C30—H301 | 111.0 | H571—C57—H572 | 109.7 |
C31—C30—H302 | 111.0 | C3—C57—H573 | 110.0 |
C29—C30—H302 | 111.0 | C56B—C57—H573 | 110.0 |
H301—C30—H302 | 109.0 | C3—C57—H574 | 110.0 |
C15—C31—C30 | 102.9 (5) | C56B—C57—H574 | 110.0 |
C15—C31—H311 | 111.2 | H573—C57—H574 | 108.4 |
C30—C31—H311 | 111.2 | N1—C59A—H591 | 109.5 |
C15—C31—H312 | 111.2 | N1—C59A—H592 | 109.5 |
C30—C31—H312 | 111.2 | H591—C59A—H592 | 109.5 |
H311—C31—H312 | 109.1 | N1—C59A—H593 | 109.5 |
C34—C33—C12 | 111.4 (6) | H591—C59A—H593 | 109.5 |
C34—C33—H331 | 109.3 | H592—C59A—H593 | 109.5 |
C12—C33—H331 | 109.3 | N1—C60A—H601 | 109.5 |
C34—C33—H332 | 109.3 | N1—C60A—H602 | 109.5 |
C12—C33—H332 | 109.3 | H601—C60A—H602 | 109.5 |
H331—C33—H332 | 108.0 | N1—C60A—H603 | 109.5 |
C35—C34—C39 | 118.9 (7) | H601—C60A—H603 | 109.5 |
C35—C34—C33 | 119.8 (6) | H602—C60A—H603 | 109.5 |
C39—C34—C33 | 121.3 (6) | N1—C59B—H594 | 109.5 |
C36—C35—C34 | 121.5 (8) | N1—C59B—H595 | 109.5 |
C36—C35—H35 | 119.3 | H594—C59B—H595 | 109.5 |
C34—C35—H35 | 119.3 | N1—C59B—H596 | 109.5 |
C35—C36—C37 | 118.9 (8) | H594—C59B—H596 | 109.5 |
C35—C36—H36 | 120.5 | H595—C59B—H596 | 109.5 |
C37—C36—H36 | 120.5 | N1—C60B—H604 | 109.5 |
C38—C37—C36 | 119.6 (8) | N1—C60B—H605 | 109.5 |
C38—C37—H37 | 120.2 | H604—C60B—H605 | 109.5 |
C36—C37—H37 | 120.2 | N1—C60B—H606 | 109.5 |
C37—C38—C39 | 120.9 (9) | H604—C60B—H606 | 109.5 |
C37—C38—H38 | 119.6 | H605—C60B—H606 | 109.5 |
C39—C38—H38 | 119.6 | C62—C61—H611 | 109.5 |
C34—C39—C38 | 120.1 (7) | C62—C61—H612 | 109.5 |
C34—C39—H39 | 119.9 | H611—C61—H612 | 109.5 |
C38—C39—H39 | 119.9 | C62—C61—H613 | 109.5 |
C42A—C41—C9 | 107.0 (6) | H611—C61—H613 | 109.5 |
C9—C41—C42B | 98.9 (9) | H612—C61—H613 | 109.5 |
C42A—C41—H411 | 110.3 | N63—C62—C61 | 175.4 (18) |
C9—C41—H411 | 110.3 | | |
| | | |
C59A—N1—C2—O58 | −175.0 (11) | C22—C21—C26—C25 | 3.2 (14) |
C60B—N1—C2—O58 | −38 (3) | C20—C21—C26—C25 | −178.4 (9) |
C59B—N1—C2—O58 | −163 (5) | N16—C15—C28—C29 | −97.1 (6) |
C60A—N1—C2—O58 | 3.6 (14) | C31—C15—C28—C29 | 22.1 (6) |
C59A—N1—C2—C3 | 6.0 (15) | C14—C15—C28—C29 | 143.1 (5) |
C60B—N1—C2—C3 | 143 (3) | C15—C28—C29—C30 | 3.1 (7) |
C59B—N1—C2—C3 | 18 (5) | C28—C29—C30—C31 | −27.1 (7) |
C60A—N1—C2—C3 | −175.3 (9) | N16—C15—C31—C30 | 78.9 (6) |
C5—N4—C3—C2 | 51.6 (8) | C14—C15—C31—C30 | −155.2 (5) |
C5—N4—C3—C57 | −73.6 (8) | C28—C15—C31—C30 | −38.9 (6) |
C5—N4—C3—C54 | 172.0 (6) | C29—C30—C31—C15 | 40.9 (7) |
O58—C2—C3—N4 | −135.4 (7) | O13—C12—C33—C34 | 65.6 (7) |
N1—C2—C3—N4 | 43.6 (10) | C11—C12—C33—C34 | −59.6 (7) |
O58—C2—C3—C57 | −12.4 (10) | C12—C33—C34—C35 | 102.9 (8) |
N1—C2—C3—C57 | 166.5 (8) | C12—C33—C34—C39 | −79.7 (8) |
O58—C2—C3—C54 | 104.1 (8) | C39—C34—C35—C36 | 3.6 (12) |
N1—C2—C3—C54 | −76.9 (9) | C33—C34—C35—C36 | −179.0 (7) |
C3—N4—C5—O53 | −5.2 (10) | C34—C35—C36—C37 | −0.8 (13) |
C3—N4—C5—C6 | 178.9 (6) | C35—C36—C37—C38 | −1.7 (14) |
C8—O7—C6—C46 | 146.1 (5) | C36—C37—C38—C39 | 1.2 (14) |
C8—O7—C6—C5 | −93.5 (6) | C35—C34—C39—C38 | −4.0 (12) |
O53—C5—C6—O7 | 178.3 (5) | C33—C34—C39—C38 | 178.6 (7) |
N4—C5—C6—O7 | −5.5 (7) | C37—C38—C39—C34 | 1.6 (14) |
O53—C5—C6—C46 | −64.9 (7) | N10—C9—C41—C42A | 95.3 (9) |
N4—C5—C6—C46 | 111.3 (6) | C8—C9—C41—C42A | −141.3 (9) |
C6—O7—C8—O45 | 6.5 (10) | C44—C9—C41—C42A | −22.7 (10) |
C6—O7—C8—C9 | −167.0 (5) | N10—C9—C41—C42B | 81.3 (9) |
C11—N10—C9—C8 | −49.7 (7) | C8—C9—C41—C42B | −155.3 (9) |
C11—N10—C9—C44 | −170.1 (5) | C44—C9—C41—C42B | −36.7 (9) |
C11—N10—C9—C41 | 75.3 (6) | C9—C41—C42A—C43A | 2.3 (15) |
O45—C8—C9—N10 | 151.2 (7) | C41—C42A—C43A—C44 | 18.8 (17) |
O7—C8—C9—N10 | −35.2 (8) | C9—C41—C42B—C43B | 53.8 (15) |
O45—C8—C9—C44 | −88.1 (8) | C41—C42B—C43B—C44 | −49.5 (19) |
O7—C8—C9—C44 | 85.5 (7) | N10—C9—C44—C43B | −112.0 (11) |
O45—C8—C9—C41 | 27.5 (10) | C8—C9—C44—C43B | 127.2 (10) |
O7—C8—C9—C41 | −158.9 (6) | C41—C9—C44—C43B | 6.4 (11) |
C9—N10—C11—O40 | −4.6 (9) | N10—C9—C44—C43A | −83.9 (8) |
C9—N10—C11—C12 | 179.0 (5) | C8—C9—C44—C43A | 155.3 (7) |
C14—O13—C12—C11 | −77.1 (6) | C41—C9—C44—C43A | 34.5 (8) |
C14—O13—C12—C33 | 159.0 (5) | C42B—C43B—C44—C9 | 26.5 (16) |
O40—C11—C12—O13 | 166.4 (5) | C42A—C43A—C44—C9 | −33.1 (14) |
N10—C11—C12—O13 | −17.0 (8) | O7—C6—C46—C47 | −58.2 (6) |
O40—C11—C12—C33 | −71.4 (7) | C5—C6—C46—C47 | −179.6 (5) |
N10—C11—C12—C33 | 105.2 (6) | C6—C46—C47—C52 | −75.6 (7) |
C12—O13—C14—O32 | 4.6 (8) | C6—C46—C47—C48 | 99.4 (7) |
C12—O13—C14—C15 | −171.3 (5) | C52—C47—C48—C49 | −2.1 (9) |
C17—N16—C15—C31 | 78.6 (7) | C46—C47—C48—C49 | −177.3 (6) |
C17—N16—C15—C14 | −49.1 (8) | C47—C48—C49—C50 | 1.7 (10) |
C17—N16—C15—C28 | −166.6 (6) | C48—C49—C50—C51 | −0.9 (11) |
O32—C14—C15—N16 | 150.1 (6) | C49—C50—C51—C52 | 0.6 (12) |
O13—C14—C15—N16 | −34.2 (7) | C50—C51—C52—C47 | −1.0 (11) |
O32—C14—C15—C31 | 23.8 (9) | C48—C47—C52—C51 | 1.8 (9) |
O13—C14—C15—C31 | −160.5 (5) | C46—C47—C52—C51 | 176.9 (6) |
O32—C14—C15—C28 | −91.0 (7) | N4—C3—C54—C55B | 94.0 (13) |
O13—C14—C15—C28 | 84.8 (6) | C2—C3—C54—C55B | −142.0 (13) |
C15—N16—C17—O27 | −0.4 (10) | C57—C3—C54—C55B | −21.6 (14) |
C15—N16—C17—C18 | 179.0 (6) | N4—C3—C54—C55A | 117.1 (10) |
O27—C17—C18—O19 | 169.8 (6) | C2—C3—C54—C55A | −118.9 (10) |
N16—C17—C18—O19 | −9.6 (9) | C57—C3—C54—C55A | 1.5 (11) |
O27—C17—C18—C20 | −65.4 (8) | C3—C54—C55A—C56A | −37.1 (15) |
N16—C17—C18—C20 | 115.2 (7) | C54—C55A—C56A—C57 | 58.7 (18) |
O19—C18—C20—C21 | −61.2 (8) | C3—C54—C55B—C56B | 17 (3) |
C17—C18—C20—C21 | 177.4 (6) | C54—C55B—C56B—C57 | −6 (3) |
C18—C20—C21—C22 | 125.1 (8) | N4—C3—C57—C56B | −97.9 (14) |
C18—C20—C21—C26 | −53.2 (10) | C2—C3—C57—C56B | 135.9 (14) |
C26—C21—C22—C23 | −2.1 (14) | C54—C3—C57—C56B | 18.0 (15) |
C20—C21—C22—C23 | 179.5 (9) | N4—C3—C57—C56A | −81.4 (9) |
C21—C22—C23—C24 | 1.3 (17) | C2—C3—C57—C56A | 152.3 (8) |
C22—C23—C24—C25 | −1.5 (16) | C54—C3—C57—C56A | 34.5 (9) |
C23—C24—C25—C26 | 2.7 (17) | C55B—C56B—C57—C3 | −8 (3) |
C24—C25—C26—C21 | −3.7 (17) | C55A—C56A—C57—C3 | −56.2 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O19—H19···O45i | 0.84 | 2.11 | 2.814 (6) | 142 |
N4—H4···O40 | 0.88 | 2.19 | 3.019 (7) | 156 |
N10—H10···O27 | 0.88 | 2.07 | 2.882 (7) | 154 |
N16—H16···O53i | 0.88 | 2.23 | 3.052 (6) | 156 |
Symmetry code: (i) x, y, z−1. |
(
S)-Pms-Aib-(
S)-Pms-Aib-NMe
2 (5a)
top
Crystal data top
C28H37N3O6 | F(000) = 1096 |
Mr = 511.60 | Dx = 1.188 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.388 (4) Å | Cell parameters from 25 reflections |
b = 12.756 (6) Å | θ = 17.5–19.5° |
c = 21.624 (5) Å | µ = 0.08 mm−1 |
β = 93.55 (3)° | T = 173 K |
V = 2859.7 (18) Å3 | Irregular prism, colourless |
Z = 4 | 0.42 × 0.35 × 0.35 mm |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.033 |
Radiation source: Rigaku RU200 rotating anode generator | θmax = 27.5°, θmin = 2.5° |
Graphite monochromator | h = −13→13 |
ω–2θ scans | k = −16→0 |
7056 measured reflections | l = −28→0 |
6868 independent reflections | 3 standard reflections every 150 reflections |
4297 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.0559P)2 + 1.181P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.149 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.33 e Å−3 |
6868 reflections | Δρmin = −0.23 e Å−3 |
703 parameters | Absolute structure: No quotients, so Flack parameter determined by classical intensity fit |
1 restraint | Absolute structure parameter: 0.0 (14) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Experimental. Solvent used: diethyl ether |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Two molecules in the asymmetric unit. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O7 | 0.6610 (3) | 0.5360 (2) | 0.12783 (13) | 0.0346 (7) | |
O13 | 0.6470 (3) | 0.1953 (3) | 0.19026 (16) | 0.0484 (9) | |
H13 | 0.684 (5) | 0.163 (5) | 0.159 (3) | 0.063 (18)* | |
O21 | 0.4396 (3) | 0.4102 (3) | 0.14925 (13) | 0.0402 (8) | |
O24 | 0.5569 (4) | 0.6639 (3) | 0.17617 (16) | 0.0551 (9) | |
O32 | 0.5683 (3) | 0.6415 (3) | −0.02233 (15) | 0.0511 (9) | |
O35 | 0.2719 (3) | 0.5974 (3) | −0.09069 (15) | 0.0562 (10) | |
N1 | 0.2739 (4) | 0.6597 (4) | 0.0063 (2) | 0.0492 (11) | |
N4 | 0.4842 (4) | 0.5082 (3) | 0.03249 (18) | 0.0375 (9) | |
H4 | 0.480 (5) | 0.479 (5) | 0.070 (3) | 0.066 (18)* | |
N10 | 0.6122 (4) | 0.3962 (4) | 0.21722 (18) | 0.0402 (9) | |
H10 | 0.653 (4) | 0.353 (4) | 0.238 (2) | 0.029 (12)* | |
C2 | 0.3049 (4) | 0.5873 (4) | −0.0349 (2) | 0.0409 (11) | |
C3 | 0.3780 (4) | 0.4862 (4) | −0.0143 (2) | 0.0405 (11) | |
C5 | 0.5698 (4) | 0.5855 (4) | 0.0236 (2) | 0.0360 (10) | |
C6 | 0.6743 (4) | 0.6041 (4) | 0.07540 (19) | 0.0347 (10) | |
H6 | 0.6675 | 0.6783 | 0.0898 | 0.042* | |
C8 | 0.6024 (4) | 0.5776 (4) | 0.1761 (2) | 0.0391 (11) | |
C9 | 0.6128 (5) | 0.5074 (4) | 0.2346 (2) | 0.0464 (13) | |
C11 | 0.5214 (4) | 0.3549 (4) | 0.1777 (2) | 0.0373 (11) | |
C12 | 0.5236 (4) | 0.2380 (4) | 0.1696 (2) | 0.0386 (11) | |
H12 | 0.5056 | 0.2208 | 0.1248 | 0.046* | |
C14 | 0.4218 (5) | 0.1856 (4) | 0.2073 (2) | 0.0512 (14) | |
H141 | 0.4289 | 0.1089 | 0.2016 | 0.061* | |
H142 | 0.4436 | 0.2006 | 0.2516 | 0.061* | |
C15 | 0.2826 (5) | 0.2163 (4) | 0.1929 (2) | 0.0434 (12) | |
C16 | 0.2232 (5) | 0.2002 (4) | 0.1338 (2) | 0.0461 (12) | |
H16 | 0.2732 | 0.1776 | 0.1010 | 0.055* | |
C17 | 0.0921 (5) | 0.2170 (5) | 0.1228 (3) | 0.0562 (14) | |
H17 | 0.0533 | 0.2063 | 0.0823 | 0.067* | |
C18 | 0.0168 (6) | 0.2489 (5) | 0.1698 (3) | 0.0636 (16) | |
H18 | −0.0737 | 0.2575 | 0.1622 | 0.076* | |
C19 | 0.0748 (6) | 0.2684 (5) | 0.2280 (3) | 0.0631 (16) | |
H19 | 0.0243 | 0.2924 | 0.2603 | 0.076* | |
C20 | 0.2067 (6) | 0.2528 (5) | 0.2393 (2) | 0.0559 (14) | |
H20 | 0.2456 | 0.2672 | 0.2793 | 0.067* | |
C22 | 0.5005 (7) | 0.5328 (5) | 0.2745 (2) | 0.0713 (18) | |
H221 | 0.4189 | 0.5153 | 0.2517 | 0.107* | |
H222 | 0.5017 | 0.6077 | 0.2847 | 0.107* | |
H223 | 0.5089 | 0.4917 | 0.3129 | 0.107* | |
C23 | 0.7432 (6) | 0.5333 (5) | 0.2670 (3) | 0.0704 (19) | |
H231 | 0.7529 | 0.4954 | 0.3064 | 0.106* | |
H232 | 0.7486 | 0.6089 | 0.2748 | 0.106* | |
H233 | 0.8121 | 0.5123 | 0.2406 | 0.106* | |
C25 | 0.8093 (4) | 0.5879 (4) | 0.0527 (2) | 0.0433 (11) | |
H251 | 0.8151 | 0.5168 | 0.0346 | 0.052* | |
H252 | 0.8244 | 0.6395 | 0.0197 | 0.052* | |
C26 | 0.9124 (4) | 0.6002 (4) | 0.1049 (2) | 0.0442 (12) | |
C27 | 0.9936 (5) | 0.5178 (5) | 0.1217 (3) | 0.0603 (15) | |
H27 | 0.9876 | 0.4546 | 0.0985 | 0.072* | |
C28 | 1.0826 (6) | 0.5253 (5) | 0.1710 (3) | 0.075 (2) | |
H28 | 1.1385 | 0.4680 | 0.1811 | 0.089* | |
C29 | 1.0914 (5) | 0.6162 (5) | 0.2063 (3) | 0.0654 (17) | |
H29 | 1.1504 | 0.6204 | 0.2415 | 0.078* | |
C30 | 1.0133 (5) | 0.7005 (5) | 0.1895 (3) | 0.0576 (15) | |
H30 | 1.0203 | 0.7637 | 0.2128 | 0.069* | |
C31 | 0.9246 (4) | 0.6935 (4) | 0.1388 (2) | 0.0457 (12) | |
H31 | 0.8722 | 0.7521 | 0.1271 | 0.055* | |
C33 | 0.2828 (5) | 0.4091 (4) | 0.0134 (2) | 0.0505 (13) | |
H331 | 0.3271 | 0.3429 | 0.0235 | 0.076* | |
H332 | 0.2104 | 0.3962 | −0.0168 | 0.076* | |
H333 | 0.2506 | 0.4393 | 0.0511 | 0.076* | |
C34 | 0.4343 (5) | 0.4347 (5) | −0.0701 (2) | 0.0573 (15) | |
H341 | 0.4911 | 0.4845 | −0.0896 | 0.086* | |
H342 | 0.3641 | 0.4140 | −0.1000 | 0.086* | |
H343 | 0.4838 | 0.3725 | −0.0566 | 0.086* | |
C36 | 0.2952 (5) | 0.6555 (5) | 0.0734 (2) | 0.0537 (14) | |
H361 | 0.3070 | 0.5824 | 0.0866 | 0.081* | |
H362 | 0.2204 | 0.6852 | 0.0927 | 0.081* | |
H363 | 0.3725 | 0.6959 | 0.0862 | 0.081* | |
C37 | 0.2188 (6) | 0.7596 (5) | −0.0161 (3) | 0.0753 (19) | |
H371 | 0.2791 | 0.8166 | −0.0049 | 0.113* | |
H372 | 0.1370 | 0.7720 | 0.0030 | 0.113* | |
H373 | 0.2036 | 0.7569 | −0.0612 | 0.113* | |
O47 | 0.0451 (3) | 0.4527 (2) | 0.64513 (13) | 0.0356 (7) | |
O53 | 0.2356 (3) | 0.7840 (3) | 0.67259 (14) | 0.0415 (8) | |
H53 | 0.165 (6) | 0.818 (5) | 0.664 (3) | 0.061 (18)* | |
O61 | 0.2545 (3) | 0.5468 (3) | 0.58551 (13) | 0.0369 (7) | |
O64 | 0.1722 (3) | 0.3097 (3) | 0.64854 (19) | 0.0578 (10) | |
O72 | −0.1299 (3) | 0.3545 (3) | 0.50820 (15) | 0.0516 (9) | |
O75 | −0.0157 (3) | 0.3802 (3) | 0.36654 (14) | 0.0412 (8) | |
N41 | 0.1294 (4) | 0.3169 (3) | 0.43905 (18) | 0.0425 (10) | |
N44 | 0.0280 (3) | 0.4770 (3) | 0.51904 (17) | 0.0361 (9) | |
H44 | 0.084 (5) | 0.512 (4) | 0.541 (2) | 0.041 (14)* | |
N50 | 0.2471 (4) | 0.5744 (3) | 0.68817 (18) | 0.0374 (9) | |
H50 | 0.256 (4) | 0.619 (4) | 0.717 (2) | 0.025 (12)* | |
C42 | 0.0477 (4) | 0.3928 (4) | 0.41641 (19) | 0.0344 (10) | |
C43 | 0.0361 (4) | 0.4959 (4) | 0.4517 (2) | 0.0379 (11) | |
C45 | −0.0539 (4) | 0.4068 (4) | 0.5411 (2) | 0.0398 (11) | |
C46 | −0.0562 (4) | 0.3936 (4) | 0.6116 (2) | 0.0365 (10) | |
H46 | −0.0475 | 0.3176 | 0.6225 | 0.044* | |
C48 | 0.1549 (4) | 0.3994 (4) | 0.6620 (2) | 0.0368 (10) | |
C49 | 0.2512 (5) | 0.4624 (4) | 0.7039 (2) | 0.0457 (12) | |
C51 | 0.2558 (4) | 0.6074 (4) | 0.62956 (19) | 0.0317 (10) | |
C52 | 0.2706 (4) | 0.7252 (4) | 0.6204 (2) | 0.0328 (10) | |
H52 | 0.2135 | 0.7469 | 0.5837 | 0.039* | |
C54 | 0.4098 (4) | 0.7512 (4) | 0.6074 (2) | 0.0405 (11) | |
H541 | 0.4165 | 0.8279 | 0.6014 | 0.049* | |
H542 | 0.4657 | 0.7328 | 0.6446 | 0.049* | |
C55 | 0.4624 (4) | 0.6970 (4) | 0.5519 (2) | 0.0346 (10) | |
C56 | 0.4328 (4) | 0.7354 (4) | 0.4924 (2) | 0.0451 (12) | |
H56 | 0.3784 | 0.7949 | 0.4866 | 0.054* | |
C57 | 0.4824 (5) | 0.6872 (5) | 0.4417 (2) | 0.0556 (15) | |
H57 | 0.4626 | 0.7144 | 0.4013 | 0.067* | |
C58 | 0.5604 (5) | 0.5998 (5) | 0.4493 (3) | 0.0586 (16) | |
H58 | 0.5939 | 0.5669 | 0.4143 | 0.070* | |
C59 | 0.5894 (5) | 0.5606 (4) | 0.5080 (2) | 0.0481 (13) | |
H59 | 0.6427 | 0.5005 | 0.5137 | 0.058* | |
C60 | 0.5404 (4) | 0.6094 (4) | 0.5582 (2) | 0.0434 (12) | |
H60 | 0.5609 | 0.5820 | 0.5985 | 0.052* | |
C62 | 0.2094 (7) | 0.4486 (6) | 0.7695 (3) | 0.078 (2) | |
H621 | 0.2683 | 0.4873 | 0.7984 | 0.118* | |
H622 | 0.2115 | 0.3739 | 0.7804 | 0.118* | |
H623 | 0.1216 | 0.4755 | 0.7721 | 0.118* | |
C63 | 0.3868 (5) | 0.4185 (5) | 0.6979 (3) | 0.0711 (19) | |
H631 | 0.4108 | 0.4261 | 0.6550 | 0.107* | |
H632 | 0.3882 | 0.3441 | 0.7093 | 0.107* | |
H633 | 0.4483 | 0.4570 | 0.7256 | 0.107* | |
C65 | −0.1860 (4) | 0.4350 (4) | 0.6317 (2) | 0.0458 (12) | |
H651 | −0.1899 | 0.5115 | 0.6241 | 0.055* | |
H652 | −0.2562 | 0.4020 | 0.6054 | 0.055* | |
C66 | −0.2097 (4) | 0.4148 (4) | 0.6988 (2) | 0.0455 (12) | |
C67 | −0.1530 (7) | 0.4779 (5) | 0.7455 (3) | 0.0712 (18) | |
H67 | −0.0966 | 0.5328 | 0.7349 | 0.085* | |
C68 | −0.1773 (10) | 0.4620 (6) | 0.8070 (3) | 0.099 (3) | |
H68 | −0.1363 | 0.5048 | 0.8383 | 0.119* | |
C69 | −0.2588 (8) | 0.3863 (8) | 0.8223 (4) | 0.090 (3) | |
H69 | −0.2758 | 0.3770 | 0.8646 | 0.108* | |
C70 | −0.3182 (6) | 0.3219 (7) | 0.7786 (4) | 0.089 (3) | |
H70 | −0.3768 | 0.2691 | 0.7899 | 0.107* | |
C71 | −0.2899 (5) | 0.3363 (5) | 0.7160 (3) | 0.0668 (18) | |
H71 | −0.3273 | 0.2904 | 0.6853 | 0.080* | |
C73 | −0.0861 (5) | 0.5530 (5) | 0.4267 (2) | 0.0612 (16) | |
H731 | −0.1605 | 0.5061 | 0.4286 | 0.092* | |
H732 | −0.0765 | 0.5738 | 0.3836 | 0.092* | |
H733 | −0.0995 | 0.6155 | 0.4518 | 0.092* | |
C74 | 0.1521 (5) | 0.5662 (4) | 0.4413 (2) | 0.0526 (14) | |
H741 | 0.1400 | 0.6345 | 0.4608 | 0.079* | |
H742 | 0.1600 | 0.5759 | 0.3967 | 0.079* | |
H743 | 0.2308 | 0.5333 | 0.4596 | 0.079* | |
C76 | 0.2228 (5) | 0.3228 (5) | 0.4917 (2) | 0.0546 (14) | |
H761 | 0.2431 | 0.3965 | 0.5008 | 0.082* | |
H762 | 0.3016 | 0.2858 | 0.4820 | 0.082* | |
H763 | 0.1867 | 0.2903 | 0.5278 | 0.082* | |
C77 | 0.1273 (6) | 0.2154 (4) | 0.4068 (3) | 0.0592 (15) | |
H771 | 0.0542 | 0.2135 | 0.3759 | 0.089* | |
H772 | 0.1184 | 0.1588 | 0.4369 | 0.089* | |
H773 | 0.2079 | 0.2062 | 0.3862 | 0.089* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O7 | 0.0334 (15) | 0.0385 (17) | 0.0310 (16) | −0.0017 (14) | −0.0054 (12) | 0.0038 (14) |
O13 | 0.0488 (19) | 0.061 (2) | 0.0342 (18) | 0.0094 (18) | −0.0121 (15) | −0.0085 (18) |
O21 | 0.0389 (16) | 0.052 (2) | 0.0279 (15) | −0.0077 (15) | −0.0080 (13) | 0.0125 (15) |
O24 | 0.072 (2) | 0.052 (2) | 0.042 (2) | 0.020 (2) | 0.0058 (17) | 0.0010 (18) |
O32 | 0.0487 (19) | 0.065 (2) | 0.0384 (19) | −0.0080 (18) | −0.0073 (15) | 0.0198 (18) |
O35 | 0.050 (2) | 0.078 (3) | 0.0381 (19) | −0.0114 (19) | −0.0166 (15) | 0.0151 (19) |
N1 | 0.044 (2) | 0.053 (3) | 0.048 (3) | 0.006 (2) | −0.0153 (19) | 0.000 (2) |
N4 | 0.037 (2) | 0.046 (2) | 0.028 (2) | −0.0034 (18) | −0.0057 (16) | 0.0045 (18) |
N10 | 0.045 (2) | 0.041 (2) | 0.031 (2) | −0.007 (2) | −0.0166 (17) | 0.0045 (19) |
C2 | 0.035 (2) | 0.055 (3) | 0.032 (2) | −0.007 (2) | −0.0063 (19) | 0.007 (2) |
C3 | 0.042 (2) | 0.055 (3) | 0.024 (2) | −0.003 (2) | −0.0050 (18) | −0.002 (2) |
C5 | 0.033 (2) | 0.042 (3) | 0.032 (2) | −0.002 (2) | −0.0010 (18) | 0.003 (2) |
C6 | 0.036 (2) | 0.037 (3) | 0.031 (2) | −0.004 (2) | −0.0021 (18) | 0.006 (2) |
C8 | 0.037 (2) | 0.044 (3) | 0.035 (2) | −0.004 (2) | −0.0068 (19) | 0.003 (2) |
C9 | 0.066 (3) | 0.042 (3) | 0.029 (2) | −0.009 (2) | −0.013 (2) | 0.001 (2) |
C11 | 0.039 (2) | 0.047 (3) | 0.025 (2) | −0.008 (2) | −0.0026 (19) | 0.008 (2) |
C12 | 0.042 (2) | 0.047 (3) | 0.025 (2) | −0.003 (2) | −0.0095 (18) | 0.000 (2) |
C14 | 0.057 (3) | 0.051 (3) | 0.044 (3) | −0.019 (3) | −0.017 (2) | 0.013 (3) |
C15 | 0.049 (3) | 0.042 (3) | 0.039 (3) | −0.016 (2) | 0.001 (2) | 0.009 (2) |
C16 | 0.045 (3) | 0.053 (3) | 0.039 (3) | −0.005 (2) | −0.004 (2) | 0.000 (2) |
C17 | 0.048 (3) | 0.059 (4) | 0.060 (3) | 0.001 (3) | −0.005 (3) | 0.001 (3) |
C18 | 0.052 (3) | 0.064 (4) | 0.076 (4) | 0.003 (3) | 0.011 (3) | 0.015 (3) |
C19 | 0.077 (4) | 0.055 (4) | 0.061 (4) | 0.006 (3) | 0.031 (3) | 0.006 (3) |
C20 | 0.077 (4) | 0.055 (4) | 0.036 (3) | −0.015 (3) | 0.007 (3) | 0.004 (3) |
C22 | 0.119 (5) | 0.063 (4) | 0.034 (3) | −0.001 (4) | 0.020 (3) | −0.004 (3) |
C23 | 0.095 (5) | 0.046 (3) | 0.063 (4) | −0.024 (3) | −0.044 (3) | 0.016 (3) |
C25 | 0.036 (2) | 0.043 (3) | 0.050 (3) | −0.003 (2) | 0.000 (2) | 0.004 (2) |
C26 | 0.027 (2) | 0.044 (3) | 0.061 (3) | −0.006 (2) | 0.002 (2) | 0.004 (3) |
C27 | 0.047 (3) | 0.041 (3) | 0.091 (4) | 0.000 (3) | −0.011 (3) | 0.006 (3) |
C28 | 0.054 (3) | 0.049 (4) | 0.115 (6) | −0.002 (3) | −0.033 (4) | 0.024 (4) |
C29 | 0.047 (3) | 0.066 (4) | 0.080 (4) | −0.021 (3) | −0.020 (3) | 0.016 (3) |
C30 | 0.043 (3) | 0.053 (3) | 0.075 (4) | −0.019 (3) | −0.010 (3) | −0.006 (3) |
C31 | 0.038 (2) | 0.045 (3) | 0.054 (3) | 0.000 (2) | −0.002 (2) | 0.003 (3) |
C33 | 0.053 (3) | 0.055 (3) | 0.041 (3) | −0.010 (3) | −0.014 (2) | 0.001 (3) |
C34 | 0.060 (3) | 0.072 (4) | 0.037 (3) | 0.004 (3) | −0.009 (2) | −0.009 (3) |
C36 | 0.047 (3) | 0.068 (4) | 0.046 (3) | −0.001 (3) | 0.001 (2) | −0.009 (3) |
C37 | 0.072 (4) | 0.069 (4) | 0.082 (5) | 0.019 (3) | −0.024 (3) | 0.004 (4) |
O47 | 0.0326 (15) | 0.0390 (17) | 0.0347 (16) | −0.0058 (14) | −0.0030 (13) | −0.0016 (14) |
O53 | 0.0399 (19) | 0.051 (2) | 0.0321 (18) | 0.0102 (17) | −0.0078 (14) | −0.0102 (16) |
O61 | 0.0332 (15) | 0.0441 (19) | 0.0334 (16) | −0.0119 (14) | 0.0016 (12) | −0.0074 (15) |
O64 | 0.044 (2) | 0.051 (2) | 0.076 (3) | 0.0011 (17) | −0.0185 (18) | −0.010 (2) |
O72 | 0.0383 (18) | 0.069 (3) | 0.046 (2) | −0.0211 (18) | −0.0079 (15) | −0.0071 (19) |
O75 | 0.0403 (17) | 0.049 (2) | 0.0330 (17) | −0.0070 (15) | −0.0049 (13) | −0.0084 (15) |
N41 | 0.037 (2) | 0.050 (3) | 0.041 (2) | 0.0055 (19) | 0.0047 (17) | 0.001 (2) |
N44 | 0.0325 (19) | 0.042 (2) | 0.033 (2) | −0.0037 (18) | −0.0063 (16) | −0.0030 (18) |
N50 | 0.044 (2) | 0.041 (2) | 0.026 (2) | −0.0081 (19) | −0.0088 (16) | −0.0020 (18) |
C42 | 0.025 (2) | 0.049 (3) | 0.029 (2) | −0.004 (2) | 0.0015 (16) | −0.005 (2) |
C43 | 0.038 (2) | 0.040 (3) | 0.034 (2) | 0.001 (2) | −0.0052 (19) | −0.006 (2) |
C45 | 0.031 (2) | 0.053 (3) | 0.034 (2) | −0.007 (2) | 0.0004 (19) | −0.007 (2) |
C46 | 0.031 (2) | 0.043 (3) | 0.036 (2) | −0.009 (2) | −0.0027 (17) | 0.000 (2) |
C48 | 0.039 (2) | 0.041 (3) | 0.030 (2) | −0.008 (2) | −0.0042 (18) | 0.002 (2) |
C49 | 0.048 (3) | 0.048 (3) | 0.039 (3) | −0.013 (2) | −0.017 (2) | 0.007 (2) |
C51 | 0.0204 (19) | 0.044 (3) | 0.029 (2) | −0.0033 (18) | −0.0091 (16) | −0.002 (2) |
C52 | 0.029 (2) | 0.041 (3) | 0.028 (2) | 0.0003 (19) | −0.0066 (16) | −0.0020 (19) |
C54 | 0.038 (2) | 0.044 (3) | 0.039 (3) | −0.009 (2) | −0.004 (2) | −0.003 (2) |
C55 | 0.0224 (19) | 0.038 (3) | 0.043 (3) | −0.0047 (19) | −0.0016 (18) | 0.006 (2) |
C56 | 0.034 (2) | 0.052 (3) | 0.049 (3) | 0.005 (2) | −0.003 (2) | 0.008 (2) |
C57 | 0.043 (3) | 0.084 (4) | 0.039 (3) | 0.008 (3) | −0.007 (2) | 0.005 (3) |
C58 | 0.040 (3) | 0.082 (4) | 0.053 (3) | 0.005 (3) | −0.003 (2) | −0.018 (3) |
C59 | 0.039 (3) | 0.047 (3) | 0.058 (3) | 0.010 (2) | −0.003 (2) | −0.002 (3) |
C60 | 0.032 (2) | 0.046 (3) | 0.051 (3) | −0.002 (2) | −0.007 (2) | 0.010 (2) |
C62 | 0.119 (5) | 0.068 (4) | 0.044 (3) | −0.043 (4) | −0.027 (3) | 0.009 (3) |
C63 | 0.050 (3) | 0.050 (4) | 0.108 (5) | −0.004 (3) | −0.040 (3) | 0.010 (3) |
C65 | 0.034 (2) | 0.059 (3) | 0.044 (3) | −0.001 (2) | 0.003 (2) | 0.014 (3) |
C66 | 0.037 (2) | 0.046 (3) | 0.054 (3) | 0.016 (2) | 0.012 (2) | 0.019 (3) |
C67 | 0.115 (5) | 0.035 (3) | 0.067 (4) | 0.012 (3) | 0.025 (4) | 0.000 (3) |
C68 | 0.179 (9) | 0.063 (5) | 0.060 (4) | 0.046 (5) | 0.039 (5) | −0.002 (4) |
C69 | 0.085 (5) | 0.113 (7) | 0.077 (5) | 0.051 (5) | 0.042 (4) | 0.044 (5) |
C70 | 0.034 (3) | 0.123 (7) | 0.112 (6) | 0.013 (4) | 0.015 (3) | 0.080 (6) |
C71 | 0.031 (2) | 0.085 (5) | 0.084 (4) | −0.004 (3) | 0.000 (3) | 0.042 (4) |
C73 | 0.073 (4) | 0.067 (4) | 0.042 (3) | 0.029 (3) | −0.013 (3) | −0.007 (3) |
C74 | 0.070 (3) | 0.046 (3) | 0.040 (3) | −0.018 (3) | −0.006 (2) | 0.006 (2) |
C76 | 0.053 (3) | 0.058 (4) | 0.051 (3) | 0.020 (3) | −0.010 (2) | −0.005 (3) |
C77 | 0.084 (4) | 0.036 (3) | 0.058 (3) | 0.008 (3) | 0.005 (3) | −0.001 (3) |
Geometric parameters (Å, º) top
O7—C8 | 1.350 (6) | O47—C48 | 1.358 (5) |
O7—C6 | 1.442 (5) | O47—C46 | 1.452 (5) |
O13—C12 | 1.438 (5) | O53—C52 | 1.421 (5) |
O13—H13 | 0.90 (6) | O53—H53 | 0.86 (6) |
O21—C11 | 1.238 (5) | O61—C51 | 1.227 (5) |
O24—C8 | 1.198 (6) | O64—C48 | 1.198 (6) |
O32—C5 | 1.222 (5) | O72—C45 | 1.226 (5) |
O35—C2 | 1.239 (5) | O75—C42 | 1.239 (5) |
N1—C2 | 1.336 (7) | N41—C42 | 1.359 (6) |
N1—C36 | 1.457 (6) | N41—C76 | 1.451 (6) |
N1—C37 | 1.466 (7) | N41—C77 | 1.470 (7) |
N4—C5 | 1.350 (6) | N44—C45 | 1.343 (6) |
N4—C3 | 1.476 (5) | N44—C43 | 1.483 (6) |
N4—H4 | 0.90 (6) | N44—H44 | 0.85 (5) |
N10—C11 | 1.341 (6) | N50—C51 | 1.344 (6) |
N10—C9 | 1.467 (7) | N50—C49 | 1.468 (7) |
N10—H10 | 0.81 (5) | N50—H50 | 0.84 (5) |
C2—C3 | 1.549 (7) | C42—C43 | 1.529 (7) |
C3—C34 | 1.522 (7) | C43—C74 | 1.531 (7) |
C3—C33 | 1.541 (7) | C43—C73 | 1.533 (7) |
C5—C6 | 1.530 (6) | C45—C46 | 1.535 (6) |
C6—C25 | 1.528 (6) | C46—C65 | 1.536 (6) |
C6—H6 | 1.0000 | C46—H46 | 1.0000 |
C8—C9 | 1.547 (7) | C48—C49 | 1.534 (6) |
C9—C23 | 1.522 (7) | C49—C62 | 1.521 (8) |
C9—C22 | 1.529 (8) | C49—C63 | 1.529 (8) |
C11—C12 | 1.502 (7) | C51—C52 | 1.524 (7) |
C12—C14 | 1.528 (7) | C52—C54 | 1.527 (6) |
C12—H12 | 1.0000 | C52—H52 | 1.0000 |
C14—C15 | 1.512 (7) | C54—C55 | 1.516 (7) |
C14—H141 | 0.9900 | C54—H541 | 0.9900 |
C14—H142 | 0.9900 | C54—H542 | 0.9900 |
C15—C20 | 1.394 (8) | C55—C60 | 1.383 (7) |
C15—C16 | 1.399 (6) | C55—C56 | 1.393 (7) |
C16—C17 | 1.384 (7) | C56—C57 | 1.383 (8) |
C16—H16 | 0.9500 | C56—H56 | 0.9500 |
C17—C18 | 1.381 (8) | C57—C58 | 1.381 (8) |
C17—H17 | 0.9500 | C57—H57 | 0.9500 |
C18—C19 | 1.384 (9) | C58—C59 | 1.381 (8) |
C18—H18 | 0.9500 | C58—H58 | 0.9500 |
C19—C20 | 1.391 (8) | C59—C60 | 1.375 (7) |
C19—H19 | 0.9500 | C59—H59 | 0.9500 |
C20—H20 | 0.9500 | C60—H60 | 0.9500 |
C22—H221 | 0.9800 | C62—H621 | 0.9800 |
C22—H222 | 0.9800 | C62—H622 | 0.9800 |
C22—H223 | 0.9800 | C62—H623 | 0.9800 |
C23—H231 | 0.9800 | C63—H631 | 0.9800 |
C23—H232 | 0.9800 | C63—H632 | 0.9800 |
C23—H233 | 0.9800 | C63—H633 | 0.9800 |
C25—C26 | 1.515 (6) | C65—C66 | 1.509 (7) |
C25—H251 | 0.9900 | C65—H651 | 0.9900 |
C25—H252 | 0.9900 | C65—H652 | 0.9900 |
C26—C27 | 1.382 (7) | C66—C71 | 1.369 (7) |
C26—C31 | 1.399 (7) | C66—C67 | 1.393 (8) |
C27—C28 | 1.371 (8) | C67—C68 | 1.384 (9) |
C27—H27 | 0.9500 | C67—H67 | 0.9500 |
C28—C29 | 1.388 (9) | C68—C69 | 1.338 (12) |
C28—H28 | 0.9500 | C68—H68 | 0.9500 |
C29—C30 | 1.382 (8) | C69—C70 | 1.371 (11) |
C29—H29 | 0.9500 | C69—H69 | 0.9500 |
C30—C31 | 1.391 (7) | C70—C71 | 1.413 (9) |
C30—H30 | 0.9500 | C70—H70 | 0.9500 |
C31—H31 | 0.9500 | C71—H71 | 0.9500 |
C33—H331 | 0.9800 | C73—H731 | 0.9800 |
C33—H332 | 0.9800 | C73—H732 | 0.9800 |
C33—H333 | 0.9800 | C73—H733 | 0.9800 |
C34—H341 | 0.9800 | C74—H741 | 0.9800 |
C34—H342 | 0.9800 | C74—H742 | 0.9800 |
C34—H343 | 0.9800 | C74—H743 | 0.9800 |
C36—H361 | 0.9800 | C76—H761 | 0.9800 |
C36—H362 | 0.9800 | C76—H762 | 0.9800 |
C36—H363 | 0.9800 | C76—H763 | 0.9800 |
C37—H371 | 0.9800 | C77—H771 | 0.9800 |
C37—H372 | 0.9800 | C77—H772 | 0.9800 |
C37—H373 | 0.9800 | C77—H773 | 0.9800 |
| | | |
C8—O7—C6 | 116.2 (4) | C48—O47—C46 | 116.4 (4) |
C12—O13—H13 | 111 (4) | C52—O53—H53 | 110 (4) |
C2—N1—C36 | 127.7 (4) | C42—N41—C76 | 128.1 (4) |
C2—N1—C37 | 119.1 (4) | C42—N41—C77 | 117.8 (4) |
C36—N1—C37 | 113.1 (5) | C76—N41—C77 | 114.1 (4) |
C5—N4—C3 | 120.8 (4) | C45—N44—C43 | 122.2 (4) |
C5—N4—H4 | 120 (4) | C45—N44—H44 | 125 (3) |
C3—N4—H4 | 118 (4) | C43—N44—H44 | 113 (3) |
C11—N10—C9 | 122.3 (4) | C51—N50—C49 | 121.4 (4) |
C11—N10—H10 | 114 (3) | C51—N50—H50 | 118 (3) |
C9—N10—H10 | 121 (3) | C49—N50—H50 | 119 (3) |
O35—C2—N1 | 120.9 (5) | O75—C42—N41 | 120.5 (4) |
O35—C2—C3 | 117.9 (5) | O75—C42—C43 | 119.5 (4) |
N1—C2—C3 | 121.1 (4) | N41—C42—C43 | 120.0 (4) |
N4—C3—C34 | 108.5 (4) | N44—C43—C42 | 111.2 (4) |
N4—C3—C33 | 109.0 (4) | N44—C43—C74 | 109.5 (4) |
C34—C3—C33 | 108.7 (4) | C42—C43—C74 | 110.1 (4) |
N4—C3—C2 | 111.8 (4) | N44—C43—C73 | 109.2 (4) |
C34—C3—C2 | 109.6 (4) | C42—C43—C73 | 108.8 (4) |
C33—C3—C2 | 109.2 (4) | C74—C43—C73 | 108.2 (5) |
O32—C5—N4 | 124.6 (4) | O72—C45—N44 | 123.8 (4) |
O32—C5—C6 | 118.5 (4) | O72—C45—C46 | 117.8 (4) |
N4—C5—C6 | 116.9 (4) | N44—C45—C46 | 118.3 (4) |
O7—C6—C25 | 107.8 (3) | O47—C46—C45 | 112.6 (4) |
O7—C6—C5 | 112.6 (3) | O47—C46—C65 | 107.5 (4) |
C25—C6—C5 | 111.6 (4) | C45—C46—C65 | 108.1 (4) |
O7—C6—H6 | 108.3 | O47—C46—H46 | 109.5 |
C25—C6—H6 | 108.3 | C45—C46—H46 | 109.5 |
C5—C6—H6 | 108.3 | C65—C46—H46 | 109.5 |
O24—C8—O7 | 124.0 (4) | O64—C48—O47 | 123.3 (4) |
O24—C8—C9 | 122.6 (4) | O64—C48—C49 | 122.8 (4) |
O7—C8—C9 | 113.1 (4) | O47—C48—C49 | 113.7 (4) |
N10—C9—C23 | 108.5 (5) | N50—C49—C62 | 108.8 (5) |
N10—C9—C22 | 111.0 (5) | N50—C49—C63 | 110.6 (4) |
C23—C9—C22 | 112.5 (5) | C62—C49—C63 | 110.7 (5) |
N10—C9—C8 | 110.6 (4) | N50—C49—C48 | 111.4 (4) |
C23—C9—C8 | 105.4 (4) | C62—C49—C48 | 106.1 (4) |
C22—C9—C8 | 108.8 (4) | C63—C49—C48 | 109.2 (5) |
O21—C11—N10 | 121.8 (5) | O61—C51—N50 | 122.4 (4) |
O21—C11—C12 | 121.5 (4) | O61—C51—C52 | 121.1 (4) |
N10—C11—C12 | 116.7 (4) | N50—C51—C52 | 116.4 (4) |
O13—C12—C11 | 111.1 (4) | O53—C52—C51 | 112.6 (4) |
O13—C12—C14 | 107.6 (4) | O53—C52—C54 | 108.8 (3) |
C11—C12—C14 | 110.9 (4) | C51—C52—C54 | 110.0 (4) |
O13—C12—H12 | 109.1 | O53—C52—H52 | 108.4 |
C11—C12—H12 | 109.1 | C51—C52—H52 | 108.4 |
C14—C12—H12 | 109.1 | C54—C52—H52 | 108.4 |
C15—C14—C12 | 117.5 (4) | C55—C54—C52 | 116.0 (4) |
C15—C14—H141 | 107.9 | C55—C54—H541 | 108.3 |
C12—C14—H141 | 107.9 | C52—C54—H541 | 108.3 |
C15—C14—H142 | 107.9 | C55—C54—H542 | 108.3 |
C12—C14—H142 | 107.9 | C52—C54—H542 | 108.3 |
H141—C14—H142 | 107.2 | H541—C54—H542 | 107.4 |
C20—C15—C16 | 118.0 (5) | C60—C55—C56 | 118.0 (5) |
C20—C15—C14 | 121.0 (5) | C60—C55—C54 | 121.8 (4) |
C16—C15—C14 | 120.8 (5) | C56—C55—C54 | 120.2 (4) |
C17—C16—C15 | 120.5 (5) | C57—C56—C55 | 120.3 (5) |
C17—C16—H16 | 119.7 | C57—C56—H56 | 119.9 |
C15—C16—H16 | 119.7 | C55—C56—H56 | 119.9 |
C18—C17—C16 | 121.0 (5) | C58—C57—C56 | 120.6 (5) |
C18—C17—H17 | 119.5 | C58—C57—H57 | 119.7 |
C16—C17—H17 | 119.5 | C56—C57—H57 | 119.7 |
C17—C18—C19 | 119.2 (5) | C59—C58—C57 | 119.6 (5) |
C17—C18—H18 | 120.4 | C59—C58—H58 | 120.2 |
C19—C18—H18 | 120.4 | C57—C58—H58 | 120.2 |
C18—C19—C20 | 120.2 (5) | C60—C59—C58 | 119.4 (5) |
C18—C19—H19 | 119.9 | C60—C59—H59 | 120.3 |
C20—C19—H19 | 119.9 | C58—C59—H59 | 120.3 |
C19—C20—C15 | 121.0 (5) | C59—C60—C55 | 122.1 (5) |
C19—C20—H20 | 119.5 | C59—C60—H60 | 119.0 |
C15—C20—H20 | 119.5 | C55—C60—H60 | 119.0 |
C9—C22—H221 | 109.5 | C49—C62—H621 | 109.5 |
C9—C22—H222 | 109.5 | C49—C62—H622 | 109.5 |
H221—C22—H222 | 109.5 | H621—C62—H622 | 109.5 |
C9—C22—H223 | 109.5 | C49—C62—H623 | 109.5 |
H221—C22—H223 | 109.5 | H621—C62—H623 | 109.5 |
H222—C22—H223 | 109.5 | H622—C62—H623 | 109.5 |
C9—C23—H231 | 109.5 | C49—C63—H631 | 109.5 |
C9—C23—H232 | 109.5 | C49—C63—H632 | 109.5 |
H231—C23—H232 | 109.5 | H631—C63—H632 | 109.5 |
C9—C23—H233 | 109.5 | C49—C63—H633 | 109.5 |
H231—C23—H233 | 109.5 | H631—C63—H633 | 109.5 |
H232—C23—H233 | 109.5 | H632—C63—H633 | 109.5 |
C26—C25—C6 | 111.5 (4) | C66—C65—C46 | 114.3 (4) |
C26—C25—H251 | 109.3 | C66—C65—H651 | 108.7 |
C6—C25—H251 | 109.3 | C46—C65—H651 | 108.7 |
C26—C25—H252 | 109.3 | C66—C65—H652 | 108.7 |
C6—C25—H252 | 109.3 | C46—C65—H652 | 108.7 |
H251—C25—H252 | 108.0 | H651—C65—H652 | 107.6 |
C27—C26—C31 | 118.4 (5) | C71—C66—C67 | 117.6 (5) |
C27—C26—C25 | 120.6 (5) | C71—C66—C65 | 121.7 (5) |
C31—C26—C25 | 121.0 (4) | C67—C66—C65 | 120.7 (5) |
C28—C27—C26 | 121.5 (6) | C68—C67—C66 | 121.1 (7) |
C28—C27—H27 | 119.2 | C68—C67—H67 | 119.4 |
C26—C27—H27 | 119.2 | C66—C67—H67 | 119.4 |
C27—C28—C29 | 120.2 (6) | C69—C68—C67 | 119.9 (8) |
C27—C28—H28 | 119.9 | C69—C68—H68 | 120.0 |
C29—C28—H28 | 119.9 | C67—C68—H68 | 120.0 |
C30—C29—C28 | 119.3 (5) | C68—C69—C70 | 121.8 (7) |
C30—C29—H29 | 120.4 | C68—C69—H69 | 119.1 |
C28—C29—H29 | 120.4 | C70—C69—H69 | 119.1 |
C29—C30—C31 | 120.4 (6) | C69—C70—C71 | 118.0 (7) |
C29—C30—H30 | 119.8 | C69—C70—H70 | 121.0 |
C31—C30—H30 | 119.8 | C71—C70—H70 | 121.0 |
C30—C31—C26 | 120.1 (5) | C66—C71—C70 | 121.5 (7) |
C30—C31—H31 | 119.9 | C66—C71—H71 | 119.3 |
C26—C31—H31 | 119.9 | C70—C71—H71 | 119.3 |
C3—C33—H331 | 109.5 | C43—C73—H731 | 109.5 |
C3—C33—H332 | 109.5 | C43—C73—H732 | 109.5 |
H331—C33—H332 | 109.5 | H731—C73—H732 | 109.5 |
C3—C33—H333 | 109.5 | C43—C73—H733 | 109.5 |
H331—C33—H333 | 109.5 | H731—C73—H733 | 109.5 |
H332—C33—H333 | 109.5 | H732—C73—H733 | 109.5 |
C3—C34—H341 | 109.5 | C43—C74—H741 | 109.5 |
C3—C34—H342 | 109.5 | C43—C74—H742 | 109.5 |
H341—C34—H342 | 109.5 | H741—C74—H742 | 109.5 |
C3—C34—H343 | 109.5 | C43—C74—H743 | 109.5 |
H341—C34—H343 | 109.5 | H741—C74—H743 | 109.5 |
H342—C34—H343 | 109.5 | H742—C74—H743 | 109.5 |
N1—C36—H361 | 109.5 | N41—C76—H761 | 109.5 |
N1—C36—H362 | 109.5 | N41—C76—H762 | 109.5 |
H361—C36—H362 | 109.5 | H761—C76—H762 | 109.5 |
N1—C36—H363 | 109.5 | N41—C76—H763 | 109.5 |
H361—C36—H363 | 109.5 | H761—C76—H763 | 109.5 |
H362—C36—H363 | 109.5 | H762—C76—H763 | 109.5 |
N1—C37—H371 | 109.5 | N41—C77—H771 | 109.5 |
N1—C37—H372 | 109.5 | N41—C77—H772 | 109.5 |
H371—C37—H372 | 109.5 | H771—C77—H772 | 109.5 |
N1—C37—H373 | 109.5 | N41—C77—H773 | 109.5 |
H371—C37—H373 | 109.5 | H771—C77—H773 | 109.5 |
H372—C37—H373 | 109.5 | H772—C77—H773 | 109.5 |
| | | |
C36—N1—C2—O35 | 174.2 (5) | C76—N41—C42—O75 | 171.2 (5) |
C37—N1—C2—O35 | −9.9 (7) | C77—N41—C42—O75 | −7.7 (6) |
C36—N1—C2—C3 | −3.2 (7) | C76—N41—C42—C43 | −7.2 (7) |
C37—N1—C2—C3 | 172.7 (5) | C77—N41—C42—C43 | 173.9 (4) |
C5—N4—C3—C34 | 72.2 (6) | C45—N44—C43—C42 | −49.1 (5) |
C5—N4—C3—C33 | −169.6 (4) | C45—N44—C43—C74 | −170.9 (4) |
C5—N4—C3—C2 | −48.8 (6) | C45—N44—C43—C73 | 70.9 (6) |
O35—C2—C3—N4 | 139.3 (4) | O75—C42—C43—N44 | 137.3 (4) |
N1—C2—C3—N4 | −43.2 (6) | N41—C42—C43—N44 | −44.3 (5) |
O35—C2—C3—C34 | 19.0 (6) | O75—C42—C43—C74 | −101.3 (5) |
N1—C2—C3—C34 | −163.6 (4) | N41—C42—C43—C74 | 77.2 (5) |
O35—C2—C3—C33 | −100.0 (5) | O75—C42—C43—C73 | 17.1 (6) |
N1—C2—C3—C33 | 77.5 (5) | N41—C42—C43—C73 | −164.5 (4) |
C3—N4—C5—O32 | −0.8 (7) | C43—N44—C45—O72 | −1.5 (7) |
C3—N4—C5—C6 | 178.5 (4) | C43—N44—C45—C46 | −179.4 (4) |
C8—O7—C6—C25 | 137.9 (4) | C48—O47—C46—C45 | −96.0 (5) |
C8—O7—C6—C5 | −98.6 (4) | C48—O47—C46—C65 | 145.0 (4) |
O32—C5—C6—O7 | 177.3 (4) | O72—C45—C46—O47 | 175.1 (4) |
N4—C5—C6—O7 | −2.1 (6) | N44—C45—C46—O47 | −6.9 (6) |
O32—C5—C6—C25 | −61.4 (6) | O72—C45—C46—C65 | −66.2 (6) |
N4—C5—C6—C25 | 119.3 (4) | N44—C45—C46—C65 | 111.8 (5) |
C6—O7—C8—O24 | 3.8 (6) | C46—O47—C48—O64 | 2.9 (6) |
C6—O7—C8—C9 | −169.9 (3) | C46—O47—C48—C49 | −173.1 (4) |
C11—N10—C9—C23 | −166.7 (5) | C51—N50—C49—C62 | −167.4 (4) |
C11—N10—C9—C22 | 69.3 (6) | C51—N50—C49—C63 | 70.7 (5) |
C11—N10—C9—C8 | −51.5 (6) | C51—N50—C49—C48 | −50.9 (6) |
O24—C8—C9—N10 | 153.1 (5) | O64—C48—C49—N50 | 150.2 (5) |
O7—C8—C9—N10 | −33.1 (6) | O47—C48—C49—N50 | −33.8 (6) |
O24—C8—C9—C23 | −89.8 (6) | O64—C48—C49—C62 | −91.5 (6) |
O7—C8—C9—C23 | 84.0 (5) | O47—C48—C49—C62 | 84.4 (5) |
O24—C8—C9—C22 | 30.9 (6) | O64—C48—C49—C63 | 27.8 (7) |
O7—C8—C9—C22 | −155.2 (4) | O47—C48—C49—C63 | −156.2 (4) |
C9—N10—C11—O21 | 6.7 (7) | C49—N50—C51—O61 | 7.5 (6) |
C9—N10—C11—C12 | −173.3 (4) | C49—N50—C51—C52 | −171.1 (4) |
O21—C11—C12—O13 | 161.2 (4) | O61—C51—C52—O53 | 164.1 (3) |
N10—C11—C12—O13 | −18.9 (6) | N50—C51—C52—O53 | −17.2 (5) |
O21—C11—C12—C14 | −79.3 (5) | O61—C51—C52—C54 | −74.3 (5) |
N10—C11—C12—C14 | 100.7 (5) | N50—C51—C52—C54 | 104.4 (4) |
O13—C12—C14—C15 | −178.7 (4) | O53—C52—C54—C55 | −178.6 (4) |
C11—C12—C14—C15 | 59.6 (6) | C51—C52—C54—C55 | 57.7 (5) |
C12—C14—C15—C20 | −125.4 (5) | C52—C54—C55—C60 | −99.9 (5) |
C12—C14—C15—C16 | 60.2 (7) | C52—C54—C55—C56 | 80.3 (6) |
C20—C15—C16—C17 | −2.1 (8) | C60—C55—C56—C57 | −0.9 (7) |
C14—C15—C16—C17 | 172.5 (5) | C54—C55—C56—C57 | 178.9 (5) |
C15—C16—C17—C18 | −0.6 (9) | C55—C56—C57—C58 | 0.8 (8) |
C16—C17—C18—C19 | 2.6 (9) | C56—C57—C58—C59 | −0.2 (8) |
C17—C18—C19—C20 | −1.9 (9) | C57—C58—C59—C60 | −0.2 (8) |
C18—C19—C20—C15 | −0.8 (9) | C58—C59—C60—C55 | 0.1 (7) |
C16—C15—C20—C19 | 2.7 (8) | C56—C55—C60—C59 | 0.5 (7) |
C14—C15—C20—C19 | −171.8 (5) | C54—C55—C60—C59 | −179.3 (4) |
O7—C6—C25—C26 | −52.6 (5) | O47—C46—C65—C66 | −65.5 (5) |
C5—C6—C25—C26 | −176.7 (4) | C45—C46—C65—C66 | 172.6 (4) |
C6—C25—C26—C27 | 119.1 (5) | C46—C65—C66—C71 | −102.5 (5) |
C6—C25—C26—C31 | −58.5 (6) | C46—C65—C66—C67 | 79.2 (6) |
C31—C26—C27—C28 | 1.4 (9) | C71—C66—C67—C68 | −0.3 (9) |
C25—C26—C27—C28 | −176.3 (6) | C65—C66—C67—C68 | 178.0 (6) |
C26—C27—C28—C29 | 1.3 (10) | C66—C67—C68—C69 | −1.4 (11) |
C27—C28—C29—C30 | −2.8 (10) | C67—C68—C69—C70 | 1.1 (11) |
C28—C29—C30—C31 | 1.6 (9) | C68—C69—C70—C71 | 0.9 (11) |
C29—C30—C31—C26 | 1.0 (8) | C67—C66—C71—C70 | 2.4 (8) |
C27—C26—C31—C30 | −2.5 (8) | C65—C66—C71—C70 | −175.9 (5) |
C25—C26—C31—C30 | 175.1 (5) | C69—C70—C71—C66 | −2.7 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O35i | 0.90 (6) | 1.79 (6) | 2.670 (5) | 169 (5) |
N4—H4···O21 | 0.90 (6) | 1.99 (6) | 2.881 (5) | 171 (5) |
N10—H10···O53ii | 0.81 (5) | 2.36 (5) | 3.124 (5) | 157 (4) |
O53—H53···O75iii | 0.86 (6) | 1.83 (6) | 2.684 (5) | 171 (6) |
N44—H44···O61 | 0.85 (5) | 2.01 (5) | 2.824 (5) | 159 (5) |
N50—H50···O13iv | 0.84 (5) | 2.40 (5) | 3.185 (5) | 156 (4) |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y−1/2, −z+1; (iii) −x, y+1/2, −z+1; (iv) −x+1, y+1/2, −z+1. |
(
S,
R)-Pms-Acp-(
R,
S)-Pms-Acp-NMe
2/(
R,
S)-Pms-Acp-(
R,
S)-Pms-Acp-NMe
2 (1:1) (5b)
top
Crystal data top
C32H41N3O6 | F(000) = 1208 |
Mr = 563.68 | Dx = 1.251 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.937 (5) Å | Cell parameters from 24 reflections |
b = 18.319 (7) Å | θ = 15–20° |
c = 16.436 (3) Å | µ = 0.09 mm−1 |
β = 90.19 (3)° | T = 173 K |
V = 2992 (2) Å3 | Prism, colourless |
Z = 4 | 0.40 × 0.40 × 0.25 mm |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.027 |
Radiation source: Rigaku RU200 rotating anode generator | θmax = 27.5°, θmin = 2.6° |
Graphite monochromator | h = −12→12 |
ω–2θ scans | k = −23→0 |
7311 measured reflections | l = 0→21 |
6855 independent reflections | 3 standard reflections every 150 reflections |
4077 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.205 | w = 1/[σ2(Fo2) + (0.0805P)2 + 2.67P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
6855 reflections | Δρmax = 0.66 e Å−3 |
509 parameters | Δρmin = −0.66 e Å−3 |
540 restraints | |
Special details top
Experimental. Solvent used: MeCN |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The molecule contains disorder of both benzyl substituents. Two orientations
of just the phenyl ring of the central benzyl group and the entire terminal
benzyl group, including the stereogenic C-atom, were defined and the site
occupation factors of the major sites of these groups refined to 0.507 (7)
and 0.532 (4), respectively. Similarity restraints were applied to the
chemically equivalent bond lengths and angles involving all disordered
C-atoms, while neighbouring atoms within and between each disordered
arrangement were restrained to have similar atomic displacement parameters. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O7 | 0.16539 (19) | 0.80427 (10) | 0.32978 (11) | 0.0355 (5) | |
O13 | 0.4674 (2) | 0.99111 (12) | 0.27404 (13) | 0.0451 (5) | |
H131 | 0.443233 | 1.034843 | 0.278838 | 0.068* | 0.532 (4) |
H132 | 0.426640 | 1.030960 | 0.268171 | 0.068* | 0.468 (4) |
O21 | 0.2127 (2) | 0.88066 (11) | 0.17927 (12) | 0.0467 (6) | |
O26 | −0.0453 (2) | 0.81105 (12) | 0.28006 (14) | 0.0473 (5) | |
O34 | 0.1704 (2) | 0.61769 (10) | 0.26113 (11) | 0.0409 (5) | |
O39 | 0.1900 (2) | 0.56239 (10) | 0.07656 (11) | 0.0356 (4) | |
N1 | 0.0170 (2) | 0.64103 (13) | 0.08740 (14) | 0.0384 (6) | |
N4 | 0.2153 (2) | 0.72171 (12) | 0.19238 (12) | 0.0294 (5) | |
H4 | 0.220 (3) | 0.7692 (17) | 0.1946 (17) | 0.032 (8)* | |
N10 | 0.2112 (3) | 0.94402 (13) | 0.29672 (16) | 0.0400 (6) | |
H10 | 0.253 (3) | 0.9732 (18) | 0.3274 (19) | 0.039 (9)* | |
C2 | 0.1490 (3) | 0.62417 (14) | 0.09297 (15) | 0.0294 (6) | |
C3 | 0.2512 (3) | 0.68470 (13) | 0.11537 (15) | 0.0296 (6) | |
C5 | 0.1808 (3) | 0.68462 (14) | 0.25869 (15) | 0.0309 (6) | |
C6 | 0.1545 (3) | 0.72606 (15) | 0.33766 (16) | 0.0343 (6) | |
H6 | 0.062268 | 0.713672 | 0.357496 | 0.041* | |
C8 | 0.0553 (3) | 0.84091 (16) | 0.30291 (16) | 0.0354 (6) | |
C9 | 0.0725 (3) | 0.92330 (15) | 0.31334 (17) | 0.0367 (7) | |
C11 | 0.2708 (3) | 0.92252 (15) | 0.22782 (18) | 0.0410 (7) | |
C12A | 0.4022 (5) | 0.9594 (4) | 0.2049 (3) | 0.0509 (15) | 0.532 (4) |
H121 | 0.378466 | 1.000607 | 0.167610 | 0.061* | 0.532 (4) |
C14A | 0.4994 (7) | 0.9125 (4) | 0.1604 (4) | 0.0604 (12) | 0.532 (4) |
H141 | 0.448336 | 0.881743 | 0.121602 | 0.072* | 0.532 (4) |
H142 | 0.542936 | 0.879333 | 0.200182 | 0.072* | 0.532 (4) |
C15A | 0.6073 (6) | 0.9514 (4) | 0.1146 (6) | 0.0634 (11) | 0.532 (4) |
C16A | 0.6167 (7) | 1.0265 (3) | 0.1034 (5) | 0.0813 (14) | 0.532 (4) |
H161 | 0.548935 | 1.058190 | 0.123708 | 0.098* | 0.532 (4) |
C17A | 0.7284 (7) | 1.0548 (4) | 0.0613 (5) | 0.0858 (15) | 0.532 (4) |
H171 | 0.740153 | 1.106089 | 0.056578 | 0.103* | 0.532 (4) |
C18A | 0.8223 (8) | 1.0070 (4) | 0.0265 (6) | 0.0781 (14) | 0.532 (4) |
H181 | 0.884415 | 1.023615 | −0.013272 | 0.094* | 0.532 (4) |
C19A | 0.8217 (7) | 0.9346 (4) | 0.0520 (6) | 0.0725 (13) | 0.532 (4) |
H191 | 0.896498 | 0.904223 | 0.039793 | 0.087* | 0.532 (4) |
C20A | 0.7137 (7) | 0.9059 (4) | 0.0948 (5) | 0.0693 (12) | 0.532 (4) |
H201 | 0.712865 | 0.855927 | 0.110393 | 0.083* | 0.532 (4) |
C12B | 0.4176 (5) | 0.9397 (4) | 0.2165 (3) | 0.0487 (16) | 0.468 (4) |
H122 | 0.469313 | 0.893283 | 0.223864 | 0.058* | 0.468 (4) |
C14B | 0.4420 (5) | 0.9665 (4) | 0.1310 (3) | 0.0460 (12) | 0.468 (4) |
H143 | 0.388830 | 0.935194 | 0.093744 | 0.055* | 0.468 (4) |
H144 | 0.404411 | 1.016379 | 0.126985 | 0.055* | 0.468 (4) |
C15B | 0.5767 (6) | 0.9689 (4) | 0.1009 (6) | 0.0660 (12) | 0.468 (4) |
C16B | 0.6590 (7) | 0.9088 (4) | 0.1153 (5) | 0.0694 (13) | 0.468 (4) |
H162 | 0.623520 | 0.869335 | 0.146063 | 0.083* | 0.468 (4) |
C17B | 0.7906 (7) | 0.9033 (5) | 0.0870 (6) | 0.0759 (15) | 0.468 (4) |
H172 | 0.844703 | 0.862101 | 0.099806 | 0.091* | 0.468 (4) |
C18B | 0.8405 (8) | 0.9600 (5) | 0.0394 (7) | 0.0778 (14) | 0.468 (4) |
H182 | 0.927583 | 0.956351 | 0.016000 | 0.093* | 0.468 (4) |
C19B | 0.7623 (8) | 1.0222 (5) | 0.0261 (7) | 0.0858 (14) | 0.468 (4) |
H192 | 0.798956 | 1.062754 | −0.002102 | 0.103* | 0.468 (4) |
C20B | 0.6302 (8) | 1.0246 (5) | 0.0545 (6) | 0.0814 (13) | 0.468 (4) |
H202 | 0.575631 | 1.065562 | 0.041500 | 0.098* | 0.468 (4) |
C22 | −0.0308 (3) | 0.96537 (18) | 0.26110 (19) | 0.0475 (8) | |
H221 | 0.011713 | 1.008829 | 0.236250 | 0.057* | |
H222 | −0.066007 | 0.933767 | 0.217062 | 0.057* | |
C23 | −0.1440 (4) | 0.9883 (2) | 0.3178 (2) | 0.0618 (10) | |
H231 | −0.143737 | 1.041876 | 0.325222 | 0.074* | |
H232 | −0.232170 | 0.973566 | 0.294845 | 0.074* | |
C24 | −0.1194 (3) | 0.9502 (2) | 0.39842 (19) | 0.0543 (9) | |
H241 | −0.164651 | 0.902077 | 0.399811 | 0.065* | |
H242 | −0.152437 | 0.980203 | 0.444293 | 0.065* | |
C25 | 0.0324 (3) | 0.94154 (16) | 0.40240 (17) | 0.0380 (7) | |
H251 | 0.058063 | 0.901449 | 0.439745 | 0.046* | |
H252 | 0.075949 | 0.987242 | 0.420916 | 0.046* | |
C27 | 0.2572 (3) | 0.70386 (18) | 0.40233 (17) | 0.0448 (7) | |
H271 | 0.244514 | 0.735184 | 0.450780 | 0.054* | 0.507 (7) |
H272 | 0.238786 | 0.652871 | 0.418871 | 0.054* | 0.507 (7) |
H273 | 0.235521 | 0.728621 | 0.454194 | 0.054* | 0.493 (7) |
H274 | 0.251508 | 0.650535 | 0.411495 | 0.054* | 0.493 (7) |
C28A | 0.4026 (8) | 0.7093 (5) | 0.3756 (11) | 0.0515 (13) | 0.507 (7) |
C29A | 0.4673 (7) | 0.7764 (5) | 0.3641 (5) | 0.0566 (13) | 0.507 (7) |
H291 | 0.419217 | 0.820412 | 0.373624 | 0.068* | 0.507 (7) |
C30A | 0.6009 (8) | 0.7799 (5) | 0.3389 (5) | 0.0606 (14) | 0.507 (7) |
H301 | 0.644592 | 0.825742 | 0.333925 | 0.073* | 0.507 (7) |
C31A | 0.6693 (7) | 0.7165 (6) | 0.3214 (5) | 0.0608 (15) | 0.507 (7) |
H311 | 0.758127 | 0.719081 | 0.300425 | 0.073* | 0.507 (7) |
C32A | 0.6093 (7) | 0.6481 (5) | 0.3340 (5) | 0.0618 (14) | 0.507 (7) |
H321 | 0.657915 | 0.604270 | 0.324774 | 0.074* | 0.507 (7) |
C33A | 0.4765 (7) | 0.6464 (5) | 0.3605 (5) | 0.0558 (13) | 0.507 (7) |
H331 | 0.434639 | 0.600379 | 0.368528 | 0.067* | 0.507 (7) |
C28B | 0.3974 (8) | 0.7234 (5) | 0.3775 (12) | 0.0516 (13) | 0.493 (7) |
C29B | 0.4428 (7) | 0.7955 (5) | 0.3809 (5) | 0.0531 (13) | 0.493 (7) |
H292 | 0.386201 | 0.832373 | 0.402721 | 0.064* | 0.493 (7) |
C30B | 0.5705 (8) | 0.8139 (5) | 0.3525 (5) | 0.0593 (15) | 0.493 (7) |
H302 | 0.600799 | 0.863020 | 0.354963 | 0.071* | 0.493 (7) |
C31B | 0.6524 (7) | 0.7604 (6) | 0.3208 (5) | 0.0594 (14) | 0.493 (7) |
H312 | 0.738523 | 0.773295 | 0.300313 | 0.071* | 0.493 (7) |
C32B | 0.6110 (7) | 0.6873 (6) | 0.3181 (5) | 0.0621 (13) | 0.493 (7) |
H322 | 0.668896 | 0.650182 | 0.298137 | 0.075* | 0.493 (7) |
C33B | 0.4823 (7) | 0.6709 (5) | 0.3457 (5) | 0.0574 (13) | 0.493 (7) |
H332 | 0.451674 | 0.621858 | 0.342673 | 0.069* | 0.493 (7) |
C35 | 0.3942 (3) | 0.65298 (16) | 0.12363 (18) | 0.0371 (6) | |
H351 | 0.410967 | 0.635509 | 0.179758 | 0.045* | |
H352 | 0.407585 | 0.611914 | 0.085349 | 0.045* | |
C36 | 0.4868 (4) | 0.71660 (19) | 0.1029 (2) | 0.0542 (9) | |
H361 | 0.492480 | 0.751966 | 0.148284 | 0.065* | |
H362 | 0.578488 | 0.699407 | 0.089223 | 0.065* | |
C37 | 0.4171 (4) | 0.7498 (2) | 0.0291 (2) | 0.0567 (9) | |
H371 | 0.441030 | 0.722834 | −0.021011 | 0.068* | |
H372 | 0.443183 | 0.801608 | 0.022384 | 0.068* | |
C38 | 0.2658 (3) | 0.74319 (15) | 0.04646 (16) | 0.0380 (7) | |
H381 | 0.216728 | 0.727500 | −0.003071 | 0.046* | |
H382 | 0.228915 | 0.790689 | 0.064499 | 0.046* | |
C40 | −0.0437 (3) | 0.71224 (19) | 0.1009 (2) | 0.0508 (8) | |
H401 | 0.026906 | 0.749567 | 0.102728 | 0.076* | |
H402 | −0.092456 | 0.711921 | 0.152604 | 0.076* | |
H403 | −0.106403 | 0.723216 | 0.056394 | 0.076* | |
C41 | −0.0762 (3) | 0.5825 (2) | 0.0640 (2) | 0.0566 (9) | |
H411 | −0.081552 | 0.579562 | 0.004510 | 0.085* | |
H412 | −0.165696 | 0.592898 | 0.086018 | 0.085* | |
H413 | −0.043677 | 0.535888 | 0.085745 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O7 | 0.0440 (11) | 0.0297 (10) | 0.0329 (10) | −0.0095 (9) | 0.0073 (8) | −0.0065 (8) |
O13 | 0.0428 (12) | 0.0430 (12) | 0.0495 (13) | 0.0021 (10) | 0.0088 (10) | −0.0100 (10) |
O21 | 0.0672 (14) | 0.0349 (11) | 0.0380 (11) | −0.0159 (10) | 0.0186 (10) | −0.0114 (9) |
O26 | 0.0483 (13) | 0.0410 (12) | 0.0525 (13) | −0.0128 (10) | −0.0001 (10) | −0.0115 (10) |
O34 | 0.0644 (14) | 0.0269 (10) | 0.0314 (10) | −0.0057 (9) | 0.0023 (9) | 0.0015 (8) |
O39 | 0.0468 (11) | 0.0261 (10) | 0.0340 (10) | −0.0026 (8) | 0.0044 (8) | −0.0048 (8) |
N1 | 0.0393 (13) | 0.0397 (14) | 0.0363 (13) | −0.0009 (11) | −0.0034 (10) | −0.0045 (10) |
N4 | 0.0428 (13) | 0.0218 (11) | 0.0236 (10) | −0.0029 (9) | 0.0038 (9) | −0.0026 (8) |
N10 | 0.0493 (15) | 0.0314 (13) | 0.0394 (13) | −0.0142 (11) | 0.0187 (11) | −0.0136 (11) |
C2 | 0.0369 (14) | 0.0306 (14) | 0.0207 (11) | −0.0019 (11) | 0.0018 (10) | −0.0005 (10) |
C3 | 0.0410 (15) | 0.0240 (13) | 0.0237 (12) | −0.0010 (11) | 0.0031 (10) | −0.0018 (10) |
C5 | 0.0375 (14) | 0.0297 (14) | 0.0253 (12) | −0.0051 (11) | −0.0020 (11) | −0.0013 (10) |
C6 | 0.0461 (16) | 0.0305 (14) | 0.0263 (13) | −0.0104 (12) | 0.0073 (11) | −0.0026 (11) |
C8 | 0.0445 (16) | 0.0364 (15) | 0.0254 (13) | −0.0081 (13) | 0.0120 (11) | −0.0058 (11) |
C9 | 0.0467 (17) | 0.0307 (14) | 0.0330 (14) | −0.0084 (12) | 0.0143 (12) | −0.0078 (11) |
C11 | 0.0535 (18) | 0.0282 (14) | 0.0415 (16) | −0.0067 (13) | 0.0162 (14) | −0.0071 (12) |
C12A | 0.053 (3) | 0.050 (3) | 0.049 (2) | −0.010 (2) | 0.021 (2) | −0.019 (2) |
C14A | 0.062 (2) | 0.061 (2) | 0.059 (2) | −0.009 (2) | 0.0259 (19) | −0.013 (2) |
C15A | 0.058 (2) | 0.074 (2) | 0.059 (2) | −0.017 (2) | 0.022 (2) | −0.015 (2) |
C16A | 0.072 (3) | 0.097 (3) | 0.075 (3) | −0.013 (2) | 0.026 (2) | −0.006 (3) |
C17A | 0.076 (3) | 0.099 (3) | 0.083 (3) | −0.015 (3) | 0.025 (3) | 0.001 (3) |
C18A | 0.060 (3) | 0.090 (3) | 0.084 (3) | −0.013 (3) | 0.028 (2) | 0.005 (3) |
C19A | 0.061 (2) | 0.084 (3) | 0.073 (2) | −0.024 (2) | 0.023 (2) | −0.007 (2) |
C20A | 0.058 (3) | 0.083 (2) | 0.067 (2) | −0.027 (2) | 0.024 (2) | −0.018 (2) |
C12B | 0.052 (3) | 0.050 (3) | 0.045 (3) | −0.006 (2) | 0.018 (2) | −0.017 (2) |
C14B | 0.047 (2) | 0.049 (2) | 0.042 (2) | −0.010 (2) | 0.016 (2) | −0.012 (2) |
C15B | 0.060 (2) | 0.078 (2) | 0.060 (2) | −0.021 (2) | 0.021 (2) | −0.017 (2) |
C16B | 0.059 (3) | 0.082 (3) | 0.067 (2) | −0.021 (2) | 0.022 (2) | −0.021 (2) |
C17B | 0.066 (3) | 0.089 (3) | 0.073 (3) | −0.024 (3) | 0.021 (3) | −0.020 (3) |
C18B | 0.063 (3) | 0.092 (3) | 0.079 (3) | −0.021 (3) | 0.025 (2) | −0.009 (3) |
C19B | 0.076 (3) | 0.097 (3) | 0.085 (3) | −0.019 (3) | 0.030 (3) | 0.000 (2) |
C20B | 0.072 (2) | 0.094 (3) | 0.078 (3) | −0.014 (2) | 0.024 (2) | −0.003 (2) |
C22 | 0.061 (2) | 0.0433 (18) | 0.0383 (16) | −0.0010 (15) | 0.0120 (15) | −0.0005 (14) |
C23 | 0.047 (2) | 0.083 (3) | 0.056 (2) | 0.0033 (19) | 0.0089 (16) | −0.0020 (19) |
C24 | 0.0493 (19) | 0.075 (2) | 0.0383 (17) | −0.0112 (17) | 0.0120 (14) | −0.0142 (16) |
C25 | 0.0463 (17) | 0.0365 (15) | 0.0314 (14) | −0.0094 (13) | 0.0114 (12) | −0.0096 (12) |
C27 | 0.062 (2) | 0.0490 (18) | 0.0238 (13) | −0.0088 (15) | 0.0020 (13) | −0.0005 (13) |
C28A | 0.052 (2) | 0.078 (3) | 0.025 (2) | −0.020 (2) | −0.0040 (19) | −0.001 (3) |
C29A | 0.054 (2) | 0.083 (3) | 0.033 (2) | −0.020 (2) | −0.0090 (18) | 0.001 (2) |
C30A | 0.057 (2) | 0.085 (3) | 0.039 (2) | −0.022 (2) | −0.007 (2) | −0.003 (2) |
C31A | 0.054 (3) | 0.085 (4) | 0.043 (2) | −0.029 (3) | −0.003 (2) | −0.005 (3) |
C32A | 0.056 (2) | 0.086 (4) | 0.043 (2) | −0.024 (3) | 0.002 (2) | −0.003 (3) |
C33A | 0.053 (2) | 0.082 (3) | 0.033 (2) | −0.021 (2) | 0.0032 (19) | −0.003 (2) |
C28B | 0.051 (2) | 0.079 (3) | 0.025 (2) | −0.018 (2) | −0.0050 (19) | −0.002 (3) |
C29B | 0.051 (2) | 0.079 (3) | 0.029 (2) | −0.019 (2) | −0.009 (2) | −0.001 (2) |
C30B | 0.055 (3) | 0.085 (4) | 0.038 (2) | −0.016 (3) | −0.008 (2) | −0.001 (3) |
C31B | 0.052 (3) | 0.086 (4) | 0.040 (2) | −0.017 (3) | −0.004 (2) | −0.003 (3) |
C32B | 0.057 (2) | 0.087 (3) | 0.043 (2) | −0.018 (3) | 0.001 (2) | −0.004 (2) |
C33B | 0.054 (2) | 0.084 (3) | 0.035 (2) | −0.016 (2) | −0.0020 (19) | −0.002 (2) |
C35 | 0.0354 (15) | 0.0388 (16) | 0.0372 (15) | −0.0025 (12) | 0.0040 (12) | −0.0031 (12) |
C36 | 0.0478 (19) | 0.051 (2) | 0.064 (2) | −0.0145 (16) | 0.0042 (16) | −0.0016 (17) |
C37 | 0.068 (2) | 0.050 (2) | 0.052 (2) | −0.0196 (17) | 0.0148 (17) | 0.0051 (16) |
C38 | 0.0597 (19) | 0.0288 (14) | 0.0257 (13) | −0.0033 (13) | 0.0058 (12) | −0.0003 (11) |
C40 | 0.0469 (18) | 0.061 (2) | 0.0446 (17) | 0.0185 (16) | −0.0067 (14) | −0.0088 (16) |
C41 | 0.0433 (18) | 0.065 (2) | 0.061 (2) | −0.0105 (17) | −0.0129 (16) | −0.0024 (18) |
Geometric parameters (Å, º) top
O7—C8 | 1.356 (4) | C19B—C20B | 1.395 (4) |
O7—C6 | 1.443 (3) | C19B—H192 | 0.9500 |
O13—C12B | 1.423 (5) | C20B—H202 | 0.9500 |
O13—C12A | 1.429 (5) | C22—C23 | 1.522 (5) |
O13—H131 | 0.8400 | C22—H221 | 0.9900 |
O13—H132 | 0.8400 | C22—H222 | 0.9900 |
O21—C11 | 1.247 (4) | C23—C24 | 1.517 (5) |
O26—C8 | 1.198 (3) | C23—H231 | 0.9900 |
O34—C5 | 1.231 (3) | C23—H232 | 0.9900 |
O39—C2 | 1.233 (3) | C24—C25 | 1.518 (4) |
N1—C2 | 1.351 (4) | C24—H241 | 0.9900 |
N1—C40 | 1.455 (4) | C24—H242 | 0.9900 |
N1—C41 | 1.468 (4) | C25—H251 | 0.9900 |
N4—C5 | 1.330 (3) | C25—H252 | 0.9900 |
N4—C3 | 1.481 (3) | C27—C28B | 1.497 (5) |
N4—H4 | 0.87 (3) | C27—C28A | 1.516 (5) |
N10—C11 | 1.339 (4) | C27—H271 | 0.9900 |
N10—C9 | 1.457 (4) | C27—H272 | 0.9900 |
N10—H10 | 0.84 (3) | C27—H273 | 0.9900 |
C2—C3 | 1.547 (4) | C27—H274 | 0.9900 |
C3—C35 | 1.541 (4) | C28A—C33A | 1.389 (7) |
C3—C38 | 1.566 (4) | C28A—C29A | 1.400 (7) |
C5—C6 | 1.527 (4) | C29A—C30A | 1.393 (7) |
C6—C27 | 1.526 (4) | C29A—H291 | 0.9500 |
C6—H6 | 1.0000 | C30A—C31A | 1.376 (10) |
C8—C9 | 1.529 (4) | C30A—H301 | 0.9500 |
C9—C22 | 1.542 (5) | C31A—C32A | 1.403 (10) |
C9—C25 | 1.555 (4) | C31A—H311 | 0.9500 |
C11—C12B | 1.505 (5) | C32A—C33A | 1.391 (7) |
C11—C12A | 1.519 (5) | C32A—H321 | 0.9500 |
C12A—C14A | 1.488 (7) | C33A—H331 | 0.9500 |
C12A—H121 | 1.0000 | C28B—C33B | 1.382 (7) |
C14A—C15A | 1.494 (5) | C28B—C29B | 1.398 (7) |
C14A—H141 | 0.9900 | C29B—C30B | 1.395 (7) |
C14A—H142 | 0.9900 | C29B—H292 | 0.9500 |
C15A—C20A | 1.386 (4) | C30B—C31B | 1.377 (10) |
C15A—C16A | 1.393 (4) | C30B—H302 | 0.9500 |
C16A—C17A | 1.408 (4) | C31B—C32B | 1.402 (10) |
C16A—H161 | 0.9500 | C31B—H312 | 0.9500 |
C17A—C18A | 1.403 (4) | C32B—C33B | 1.391 (7) |
C17A—H171 | 0.9500 | C32B—H322 | 0.9500 |
C18A—C19A | 1.391 (4) | C33B—H332 | 0.9500 |
C18A—H181 | 0.9500 | C35—C36 | 1.525 (4) |
C19A—C20A | 1.390 (4) | C35—H351 | 0.9900 |
C19A—H191 | 0.9500 | C35—H352 | 0.9900 |
C20A—H201 | 0.9500 | C36—C37 | 1.521 (5) |
C12B—C14B | 1.508 (6) | C36—H361 | 0.9900 |
C12B—H122 | 1.0000 | C36—H362 | 0.9900 |
C14B—C15B | 1.430 (4) | C37—C38 | 1.536 (5) |
C14B—H143 | 0.9900 | C37—H371 | 0.9900 |
C14B—H144 | 0.9900 | C37—H372 | 0.9900 |
C15B—C20B | 1.382 (4) | C38—H381 | 0.9900 |
C15B—C16B | 1.391 (4) | C38—H382 | 0.9900 |
C16B—C17B | 1.393 (4) | C40—H401 | 0.9800 |
C16B—H162 | 0.9500 | C40—H402 | 0.9800 |
C17B—C18B | 1.393 (4) | C40—H403 | 0.9800 |
C17B—H172 | 0.9500 | C41—H411 | 0.9800 |
C18B—C19B | 1.395 (4) | C41—H412 | 0.9800 |
C18B—H182 | 0.9500 | C41—H413 | 0.9800 |
| | | |
C8—O7—C6 | 117.4 (2) | C9—C22—H221 | 110.4 |
C12A—O13—H131 | 109.5 | C23—C22—H222 | 110.4 |
C12B—O13—H132 | 109.5 | C9—C22—H222 | 110.4 |
C2—N1—C40 | 126.7 (2) | H221—C22—H222 | 108.6 |
C2—N1—C41 | 117.6 (2) | C24—C23—C22 | 106.9 (3) |
C40—N1—C41 | 115.7 (3) | C24—C23—H231 | 110.3 |
C5—N4—C3 | 122.0 (2) | C22—C23—H231 | 110.3 |
C5—N4—H4 | 119.2 (19) | C24—C23—H232 | 110.3 |
C3—N4—H4 | 118.7 (19) | C22—C23—H232 | 110.3 |
C11—N10—C9 | 120.2 (3) | H231—C23—H232 | 108.6 |
C11—N10—H10 | 118 (2) | C23—C24—C25 | 104.1 (3) |
C9—N10—H10 | 121 (2) | C23—C24—H241 | 110.9 |
O39—C2—N1 | 121.1 (2) | C25—C24—H241 | 110.9 |
O39—C2—C3 | 119.5 (2) | C23—C24—H242 | 110.9 |
N1—C2—C3 | 119.3 (2) | C25—C24—H242 | 110.9 |
N4—C3—C35 | 108.8 (2) | H241—C24—H242 | 109.0 |
N4—C3—C2 | 111.8 (2) | C24—C25—C9 | 103.9 (2) |
C35—C3—C2 | 110.8 (2) | C24—C25—H251 | 111.0 |
N4—C3—C38 | 109.2 (2) | C9—C25—H251 | 111.0 |
C35—C3—C38 | 103.6 (2) | C24—C25—H252 | 111.0 |
C2—C3—C38 | 112.4 (2) | C9—C25—H252 | 111.0 |
O34—C5—N4 | 123.9 (2) | H251—C25—H252 | 109.0 |
O34—C5—C6 | 116.9 (2) | C28B—C27—C6 | 111.5 (8) |
N4—C5—C6 | 119.2 (2) | C28A—C27—C6 | 114.6 (8) |
O7—C6—C27 | 106.1 (2) | C28A—C27—H271 | 108.6 |
O7—C6—C5 | 113.9 (2) | C6—C27—H271 | 108.6 |
C27—C6—C5 | 110.1 (2) | C28A—C27—H272 | 108.6 |
O7—C6—H6 | 108.9 | C6—C27—H272 | 108.6 |
C27—C6—H6 | 108.9 | H271—C27—H272 | 107.6 |
C5—C6—H6 | 108.9 | C28B—C27—H273 | 109.3 |
O26—C8—O7 | 123.2 (3) | C6—C27—H273 | 109.3 |
O26—C8—C9 | 125.4 (3) | C28B—C27—H274 | 109.3 |
O7—C8—C9 | 111.3 (2) | C6—C27—H274 | 109.3 |
N10—C9—C8 | 110.0 (2) | H273—C27—H274 | 108.0 |
N10—C9—C22 | 113.2 (2) | C33A—C28A—C29A | 117.5 (5) |
C8—C9—C22 | 110.9 (3) | C33A—C28A—C27 | 120.1 (6) |
N10—C9—C25 | 111.5 (2) | C29A—C28A—C27 | 122.4 (6) |
C8—C9—C25 | 106.8 (2) | C30A—C29A—C28A | 121.2 (6) |
C22—C9—C25 | 104.2 (2) | C30A—C29A—H291 | 119.4 |
O21—C11—N10 | 121.2 (3) | C28A—C29A—H291 | 119.4 |
O21—C11—C12B | 119.7 (3) | C31A—C30A—C29A | 119.7 (7) |
N10—C11—C12B | 118.3 (3) | C31A—C30A—H301 | 120.1 |
O21—C11—C12A | 120.8 (3) | C29A—C30A—H301 | 120.1 |
N10—C11—C12A | 117.5 (3) | C30A—C31A—C32A | 120.8 (5) |
O13—C12A—C14A | 109.4 (5) | C30A—C31A—H311 | 119.6 |
O13—C12A—C11 | 111.8 (3) | C32A—C31A—H311 | 119.6 |
C14A—C12A—C11 | 115.1 (5) | C33A—C32A—C31A | 118.1 (7) |
O13—C12A—H121 | 106.7 | C33A—C32A—H321 | 121.0 |
C14A—C12A—H121 | 106.7 | C31A—C32A—H321 | 121.0 |
C11—C12A—H121 | 106.7 | C28A—C33A—C32A | 122.7 (6) |
C12A—C14A—C15A | 116.2 (5) | C28A—C33A—H331 | 118.7 |
C12A—C14A—H141 | 108.2 | C32A—C33A—H331 | 118.7 |
C15A—C14A—H141 | 108.2 | C33B—C28B—C29B | 118.4 (5) |
C12A—C14A—H142 | 108.2 | C33B—C28B—C27 | 120.5 (6) |
C15A—C14A—H142 | 108.2 | C29B—C28B—C27 | 121.1 (6) |
H141—C14A—H142 | 107.4 | C30B—C29B—C28B | 120.6 (6) |
C20A—C15A—C16A | 120.8 (5) | C30B—C29B—H292 | 119.7 |
C20A—C15A—C14A | 112.4 (5) | C28B—C29B—H292 | 119.7 |
C16A—C15A—C14A | 125.9 (5) | C31B—C30B—C29B | 119.7 (7) |
C15A—C16A—C17A | 118.8 (4) | C31B—C30B—H302 | 120.2 |
C15A—C16A—H161 | 120.6 | C29B—C30B—H302 | 120.2 |
C17A—C16A—H161 | 120.6 | C30B—C31B—C32B | 121.2 (6) |
C18A—C17A—C16A | 119.8 (5) | C30B—C31B—H312 | 119.4 |
C18A—C17A—H171 | 120.1 | C32B—C31B—H312 | 119.4 |
C16A—C17A—H171 | 120.1 | C33B—C32B—C31B | 117.8 (7) |
C19A—C18A—C17A | 117.9 (6) | C33B—C32B—H322 | 121.1 |
C19A—C18A—H181 | 121.0 | C31B—C32B—H322 | 121.1 |
C17A—C18A—H181 | 121.0 | C28B—C33B—C32B | 122.4 (6) |
C20A—C19A—C18A | 121.2 (6) | C28B—C33B—H332 | 118.8 |
C20A—C19A—H191 | 119.4 | C32B—C33B—H332 | 118.8 |
C18A—C19A—H191 | 119.4 | C36—C35—C3 | 104.4 (3) |
C15A—C20A—C19A | 118.8 (5) | C36—C35—H351 | 110.9 |
C15A—C20A—H201 | 120.6 | C3—C35—H351 | 110.9 |
C19A—C20A—H201 | 120.6 | C36—C35—H352 | 110.9 |
O13—C12B—C11 | 113.0 (4) | C3—C35—H352 | 110.9 |
O13—C12B—C14B | 110.3 (5) | H351—C35—H352 | 108.9 |
C11—C12B—C14B | 110.0 (5) | C37—C36—C35 | 102.1 (3) |
O13—C12B—H122 | 107.8 | C37—C36—H361 | 111.3 |
C11—C12B—H122 | 107.8 | C35—C36—H361 | 111.3 |
C14B—C12B—H122 | 107.8 | C37—C36—H362 | 111.3 |
C15B—C14B—C12B | 119.1 (5) | C35—C36—H362 | 111.3 |
C15B—C14B—H143 | 107.5 | H361—C36—H362 | 109.2 |
C12B—C14B—H143 | 107.5 | C36—C37—C38 | 105.3 (3) |
C15B—C14B—H144 | 107.5 | C36—C37—H371 | 110.7 |
C12B—C14B—H144 | 107.5 | C38—C37—H371 | 110.7 |
H143—C14B—H144 | 107.0 | C36—C37—H372 | 110.7 |
C20B—C15B—C16B | 116.9 (5) | C38—C37—H372 | 110.7 |
C20B—C15B—C14B | 125.2 (6) | H371—C37—H372 | 108.8 |
C16B—C15B—C14B | 117.8 (4) | C37—C38—C3 | 106.3 (2) |
C15B—C16B—C17B | 123.5 (6) | C37—C38—H381 | 110.5 |
C15B—C16B—H162 | 118.3 | C3—C38—H381 | 110.5 |
C17B—C16B—H162 | 118.3 | C37—C38—H382 | 110.5 |
C18B—C17B—C16B | 118.1 (6) | C3—C38—H382 | 110.5 |
C18B—C17B—H172 | 121.0 | H381—C38—H382 | 108.7 |
C16B—C17B—H172 | 121.0 | N1—C40—H401 | 109.5 |
C17B—C18B—C19B | 119.8 (6) | N1—C40—H402 | 109.5 |
C17B—C18B—H182 | 120.1 | H401—C40—H402 | 109.5 |
C19B—C18B—H182 | 120.1 | N1—C40—H403 | 109.5 |
C20B—C19B—C18B | 119.9 (6) | H401—C40—H403 | 109.5 |
C20B—C19B—H192 | 120.1 | H402—C40—H403 | 109.5 |
C18B—C19B—H192 | 120.1 | N1—C41—H411 | 109.5 |
C15B—C20B—C19B | 121.7 (6) | N1—C41—H412 | 109.5 |
C15B—C20B—H202 | 119.2 | H411—C41—H412 | 109.5 |
C19B—C20B—H202 | 119.2 | N1—C41—H413 | 109.5 |
C23—C22—C9 | 106.8 (3) | H411—C41—H413 | 109.5 |
C23—C22—H221 | 110.4 | H412—C41—H413 | 109.5 |
| | | |
C40—N1—C2—O39 | −176.7 (3) | O13—C12B—C14B—C15B | 69.8 (8) |
C41—N1—C2—O39 | 2.1 (4) | C11—C12B—C14B—C15B | −164.8 (6) |
C40—N1—C2—C3 | −0.3 (4) | C12B—C14B—C15B—C20B | −138.8 (10) |
C41—N1—C2—C3 | 178.5 (2) | C12B—C14B—C15B—C16B | 44.9 (12) |
C5—N4—C3—C35 | −75.9 (3) | C20B—C15B—C16B—C17B | 1.4 (15) |
C5—N4—C3—C2 | 46.8 (3) | C14B—C15B—C16B—C17B | 177.9 (9) |
C5—N4—C3—C38 | 171.8 (2) | C15B—C16B—C17B—C18B | −2.3 (15) |
O39—C2—C3—N4 | −128.7 (2) | C16B—C17B—C18B—C19B | 4.4 (16) |
N1—C2—C3—N4 | 54.9 (3) | C17B—C18B—C19B—C20B | −5.7 (18) |
O39—C2—C3—C35 | −7.1 (3) | C16B—C15B—C20B—C19B | −2.6 (16) |
N1—C2—C3—C35 | 176.5 (2) | C14B—C15B—C20B—C19B | −178.8 (10) |
O39—C2—C3—C38 | 108.2 (3) | C18B—C19B—C20B—C15B | 4.8 (18) |
N1—C2—C3—C38 | −68.2 (3) | N10—C9—C22—C23 | −135.8 (3) |
C3—N4—C5—O34 | −3.1 (4) | C8—C9—C22—C23 | 100.0 (3) |
C3—N4—C5—C6 | 175.7 (2) | C25—C9—C22—C23 | −14.6 (3) |
C8—O7—C6—C27 | −154.2 (2) | C9—C22—C23—C24 | −8.8 (4) |
C8—O7—C6—C5 | 84.6 (3) | C22—C23—C24—C25 | 29.3 (4) |
O34—C5—C6—O7 | −178.6 (2) | C23—C24—C25—C9 | −38.1 (3) |
N4—C5—C6—O7 | 2.5 (4) | N10—C9—C25—C24 | 154.9 (3) |
O34—C5—C6—C27 | 62.4 (3) | C8—C9—C25—C24 | −85.0 (3) |
N4—C5—C6—C27 | −116.5 (3) | C22—C9—C25—C24 | 32.5 (3) |
C6—O7—C8—O26 | −5.7 (4) | O7—C6—C27—C28B | −61.0 (5) |
C6—O7—C8—C9 | 169.0 (2) | C5—C6—C27—C28B | 62.6 (5) |
C11—N10—C9—C8 | 51.3 (4) | O7—C6—C27—C28A | −71.4 (5) |
C11—N10—C9—C22 | −73.4 (3) | C5—C6—C27—C28A | 52.2 (5) |
C11—N10—C9—C25 | 169.6 (3) | C6—C27—C28A—C33A | −107.8 (14) |
O26—C8—C9—N10 | −148.1 (3) | C6—C27—C28A—C29A | 71.4 (15) |
O7—C8—C9—N10 | 37.3 (3) | C33A—C28A—C29A—C30A | −0.4 (19) |
O26—C8—C9—C22 | −22.2 (4) | C27—C28A—C29A—C30A | −179.6 (11) |
O7—C8—C9—C22 | 163.3 (2) | C28A—C29A—C30A—C31A | 3.0 (14) |
O26—C8—C9—C25 | 90.7 (3) | C29A—C30A—C31A—C32A | −4.6 (12) |
O7—C8—C9—C25 | −83.8 (3) | C30A—C31A—C32A—C33A | 3.5 (11) |
C9—N10—C11—O21 | −4.8 (5) | C29A—C28A—C33A—C32A | −1 (2) |
C9—N10—C11—C12B | −174.8 (4) | C27—C28A—C33A—C32A | 178.5 (10) |
C9—N10—C11—C12A | 166.4 (4) | C31A—C32A—C33A—C28A | −0.8 (14) |
O21—C11—C12A—O13 | −166.6 (4) | C6—C27—C28B—C33B | −100.3 (14) |
N10—C11—C12A—O13 | 22.1 (8) | C6—C27—C28B—C29B | 75.6 (15) |
O21—C11—C12A—C14A | −40.9 (8) | C33B—C28B—C29B—C30B | 0 (2) |
N10—C11—C12A—C14A | 147.8 (5) | C27—C28B—C29B—C30B | −175.7 (11) |
O13—C12A—C14A—C15A | −71.9 (8) | C28B—C29B—C30B—C31B | 0.0 (14) |
C11—C12A—C14A—C15A | 161.2 (7) | C29B—C30B—C31B—C32B | −1.4 (12) |
C12A—C14A—C15A—C20A | 162.7 (7) | C30B—C31B—C32B—C33B | 2.4 (12) |
C12A—C14A—C15A—C16A | −6.7 (13) | C29B—C28B—C33B—C32B | 1 (2) |
C20A—C15A—C16A—C17A | 8.7 (15) | C27—C28B—C33B—C32B | 176.7 (11) |
C14A—C15A—C16A—C17A | 177.3 (9) | C31B—C32B—C33B—C28B | −2.1 (15) |
C15A—C16A—C17A—C18A | 4.7 (14) | N4—C3—C35—C36 | −84.3 (3) |
C16A—C17A—C18A—C19A | −16.3 (14) | C2—C3—C35—C36 | 152.4 (2) |
C17A—C18A—C19A—C20A | 15.1 (15) | C38—C3—C35—C36 | 31.7 (3) |
C16A—C15A—C20A—C19A | −10.0 (14) | C3—C35—C36—C37 | −43.1 (3) |
C14A—C15A—C20A—C19A | 180.0 (8) | C35—C36—C37—C38 | 37.4 (3) |
C18A—C19A—C20A—C15A | −2.1 (14) | C36—C37—C38—C3 | −17.8 (3) |
O21—C11—C12B—O13 | 176.8 (4) | N4—C3—C38—C37 | 107.3 (3) |
N10—C11—C12B—O13 | −13.0 (8) | C35—C3—C38—C37 | −8.5 (3) |
O21—C11—C12B—C14B | 53.1 (7) | C2—C3—C38—C37 | −128.1 (3) |
N10—C11—C12B—C14B | −136.8 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H131···O34i | 0.84 | 2.00 | 2.753 (3) | 149 |
O13—H132···O34i | 0.84 | 1.92 | 2.753 (3) | 172 |
N4—H4···O21 | 0.87 (3) | 2.06 (3) | 2.920 (3) | 170 (3) |
N10—H10···O39i | 0.84 (3) | 2.34 (3) | 3.161 (3) | 164 (3) |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
(
R,
S)-Mns-Acp-(
S,
R)-Mns-Acp-NMe
2 (5c)
top
Crystal data top
C30H37N3O6 | Dx = 1.273 Mg m−3 |
Mr = 535.62 | Melting point: 372 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
a = 18.922 (5) Å | Cell parameters from 23 reflections |
b = 18.300 (3) Å | θ = 18–20° |
c = 8.072 (6) Å | µ = 0.09 mm−1 |
V = 2795 (2) Å3 | T = 173 K |
Z = 4 | Prism, colourless |
F(000) = 1144 | 0.30 × 0.23 × 0.20 mm |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.043 |
Radiation source: Rigaku RU200 rotating anode generator | θmax = 27.5°, θmin = 2.8° |
Graphite monochromator | h = −1→24 |
ω–2θ scans | k = 0→23 |
4363 measured reflections | l = −10→1 |
3889 independent reflections | 3 standard reflections every 150 reflections |
2106 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0586P)2 + 1.4867P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.161 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.32 e Å−3 |
3889 reflections | Δρmin = −0.24 e Å−3 |
394 parameters | Absolute structure: Flack x determined using 231 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
98 restraints | Absolute structure parameter: −3.2 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Experimental. Solvent used: dichloromethane/diethyl ether/hexane |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. One of the five-membered rings exhibits significant conformational disorder
and two positions were refined for three of the ring-atoms. The site
occupation factor of the major conformation of the ring refined to
0.658 (12). Similarity restraints were applied to the chemically equivalent
bond lengths involving all disordered C atoms, while neighbouring atoms
within and between each conformation of the disordered components were
restrained to have similar atomic displacement parameters. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O7 | 0.27446 (16) | 0.65935 (17) | 0.3454 (5) | 0.0299 (8) | |
O13 | 0.3236 (2) | 0.4369 (2) | 0.6595 (7) | 0.0529 (12) | |
H13 | 0.308 (4) | 0.403 (3) | 0.725 (8) | 0.08 (3)* | |
O20 | 0.33321 (19) | 0.62869 (18) | 0.6795 (6) | 0.0381 (9) | |
O25 | 0.36813 (19) | 0.7228 (2) | 0.2567 (7) | 0.0532 (13) | |
O32 | 0.21090 (18) | 0.84238 (19) | 0.4054 (6) | 0.0419 (10) | |
O37 | 0.2006 (2) | 0.9229 (2) | 0.7711 (6) | 0.0499 (11) | |
N1 | 0.1471 (2) | 0.8140 (2) | 0.7832 (7) | 0.0463 (13) | |
N4 | 0.2682 (2) | 0.7657 (2) | 0.5800 (6) | 0.0311 (10) | |
H4 | 0.292 (2) | 0.7272 (18) | 0.592 (8) | 0.035 (16)* | |
N10 | 0.3518 (2) | 0.5493 (2) | 0.4666 (7) | 0.0347 (11) | |
H10 | 0.347 (3) | 0.5065 (16) | 0.426 (7) | 0.036 (15)* | |
C2 | 0.2041 (3) | 0.8557 (3) | 0.7550 (8) | 0.0385 (14) | |
C3 | 0.2765 (3) | 0.8207 (3) | 0.7111 (7) | 0.0345 (13) | |
C5 | 0.2375 (3) | 0.7814 (3) | 0.4359 (7) | 0.0313 (12) | |
C6 | 0.2312 (2) | 0.7213 (3) | 0.3053 (7) | 0.0313 (12) | |
H6 | 0.2462 | 0.7413 | 0.1956 | 0.038* | |
C8 | 0.3444 (2) | 0.6681 (3) | 0.3171 (7) | 0.0330 (13) | |
C9 | 0.3889 (3) | 0.6022 (3) | 0.3607 (7) | 0.0364 (13) | |
C11 | 0.3308 (3) | 0.5661 (3) | 0.6214 (8) | 0.0326 (13) | |
C12 | 0.3037 (3) | 0.5028 (3) | 0.7310 (9) | 0.0453 (17) | |
H12 | 0.3279 | 0.5066 | 0.8408 | 0.054* | |
C14 | 0.2250 (3) | 0.5116 (3) | 0.7606 (8) | 0.0335 (13) | |
C15 | 0.1775 (4) | 0.4822 (4) | 0.6556 (11) | 0.064 (2) | |
H15 | 0.1937 | 0.4564 | 0.5607 | 0.077* | |
C16 | 0.1048 (5) | 0.4890 (5) | 0.6834 (14) | 0.087 (3) | |
H16 | 0.0714 | 0.4680 | 0.6096 | 0.104* | |
C17 | 0.0832 (4) | 0.5272 (4) | 0.8217 (16) | 0.090 (4) | |
H17 | 0.0340 | 0.5334 | 0.8398 | 0.108* | |
C18 | 0.1298 (5) | 0.5571 (4) | 0.9357 (15) | 0.082 (3) | |
H18 | 0.1137 | 0.5818 | 1.0322 | 0.099* | |
C19 | 0.2010 (4) | 0.5490 (3) | 0.9010 (10) | 0.0585 (19) | |
H19 | 0.2347 | 0.5695 | 0.9749 | 0.070* | |
C21 | 0.4590 (2) | 0.6277 (3) | 0.4484 (9) | 0.0472 (17) | |
H211 | 0.4714 | 0.6789 | 0.4214 | 0.057* | 0.342 (12) |
H212 | 0.4572 | 0.6211 | 0.5701 | 0.057* | 0.342 (12) |
H213 | 0.4619 | 0.6817 | 0.4441 | 0.057* | 0.658 (12) |
H214 | 0.4575 | 0.6130 | 0.5664 | 0.057* | 0.658 (12) |
C22A | 0.5083 (10) | 0.5727 (10) | 0.364 (2) | 0.059 (2) | 0.342 (12) |
H221 | 0.5577 | 0.5903 | 0.3662 | 0.071* | 0.342 (12) |
H222 | 0.5060 | 0.5247 | 0.4207 | 0.071* | 0.342 (12) |
C23A | 0.4812 (8) | 0.5667 (12) | 0.186 (3) | 0.060 (2) | 0.342 (12) |
H231 | 0.4978 | 0.5205 | 0.1359 | 0.072* | 0.342 (12) |
H232 | 0.4995 | 0.6079 | 0.1194 | 0.072* | 0.342 (12) |
C24A | 0.4003 (9) | 0.5685 (17) | 0.1894 (19) | 0.058 (2) | 0.342 (12) |
H241 | 0.3808 | 0.5997 | 0.1002 | 0.070* | 0.342 (12) |
H242 | 0.3797 | 0.5189 | 0.1814 | 0.070* | 0.342 (12) |
C22B | 0.5250 (4) | 0.5954 (6) | 0.3684 (17) | 0.060 (2) | 0.658 (12) |
H223 | 0.5587 | 0.5772 | 0.4527 | 0.072* | 0.658 (12) |
H224 | 0.5491 | 0.6314 | 0.2964 | 0.072* | 0.658 (12) |
C23B | 0.4934 (4) | 0.5328 (5) | 0.2677 (17) | 0.0573 (19) | 0.658 (12) |
H233 | 0.4875 | 0.4885 | 0.3367 | 0.069* | 0.658 (12) |
H234 | 0.5236 | 0.5208 | 0.1713 | 0.069* | 0.658 (12) |
C24B | 0.4218 (5) | 0.5629 (8) | 0.2120 (12) | 0.057 (2) | 0.658 (12) |
H243 | 0.3908 | 0.5225 | 0.1749 | 0.068* | 0.658 (12) |
H244 | 0.4281 | 0.5974 | 0.1187 | 0.068* | 0.658 (12) |
C26 | 0.1547 (2) | 0.6970 (3) | 0.2940 (7) | 0.0334 (12) | |
C27 | 0.1078 (3) | 0.7397 (3) | 0.2043 (9) | 0.0446 (16) | |
H27 | 0.1246 | 0.7817 | 0.1473 | 0.054* | |
C28 | 0.0370 (3) | 0.7219 (3) | 0.1972 (10) | 0.0518 (18) | |
H28 | 0.0055 | 0.7513 | 0.1344 | 0.062* | |
C29 | 0.0121 (3) | 0.6626 (4) | 0.2794 (10) | 0.0565 (19) | |
H29 | −0.0367 | 0.6505 | 0.2739 | 0.068* | |
C30 | 0.0578 (3) | 0.6197 (4) | 0.3712 (10) | 0.066 (2) | |
H30 | 0.0403 | 0.5786 | 0.4302 | 0.079* | |
C31 | 0.1294 (3) | 0.6370 (4) | 0.3772 (10) | 0.0547 (18) | |
H31 | 0.1608 | 0.6071 | 0.4390 | 0.066* | |
C33 | 0.3102 (3) | 0.7855 (3) | 0.8668 (8) | 0.0452 (15) | |
H331 | 0.2950 | 0.8116 | 0.9681 | 0.054* | |
H332 | 0.2960 | 0.7336 | 0.8763 | 0.054* | |
C34 | 0.3901 (3) | 0.7917 (4) | 0.8443 (11) | 0.070 (2) | |
H341 | 0.4116 | 0.7428 | 0.8305 | 0.085* | |
H342 | 0.4119 | 0.8158 | 0.9415 | 0.085* | |
C35 | 0.4008 (3) | 0.8379 (4) | 0.6881 (11) | 0.066 (2) | |
H351 | 0.4402 | 0.8728 | 0.7035 | 0.079* | |
H352 | 0.4115 | 0.8063 | 0.5918 | 0.079* | |
C36 | 0.3313 (3) | 0.8784 (3) | 0.6619 (9) | 0.0426 (14) | |
H361 | 0.3255 | 0.8934 | 0.5448 | 0.051* | |
H362 | 0.3282 | 0.9221 | 0.7339 | 0.051* | |
C38 | 0.1422 (4) | 0.7336 (3) | 0.7716 (10) | 0.061 (2) | |
H381 | 0.1272 | 0.7198 | 0.6597 | 0.092* | |
H382 | 0.1077 | 0.7157 | 0.8524 | 0.092* | |
H383 | 0.1885 | 0.7120 | 0.7950 | 0.092* | |
C39 | 0.0805 (3) | 0.8526 (4) | 0.8168 (12) | 0.072 (2) | |
H391 | 0.0829 | 0.8757 | 0.9262 | 0.107* | |
H392 | 0.0412 | 0.8176 | 0.8146 | 0.107* | |
H393 | 0.0729 | 0.8901 | 0.7321 | 0.107* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O7 | 0.0282 (17) | 0.0290 (17) | 0.033 (2) | −0.0035 (15) | −0.0015 (17) | 0.0000 (17) |
O13 | 0.063 (3) | 0.036 (2) | 0.059 (3) | 0.010 (2) | 0.027 (3) | 0.014 (2) |
O20 | 0.050 (2) | 0.0253 (18) | 0.039 (2) | 0.0087 (16) | −0.001 (2) | 0.0017 (19) |
O25 | 0.035 (2) | 0.046 (2) | 0.078 (4) | −0.0047 (17) | −0.001 (2) | 0.032 (3) |
O32 | 0.050 (2) | 0.032 (2) | 0.044 (3) | 0.0000 (17) | −0.016 (2) | 0.010 (2) |
O37 | 0.061 (2) | 0.030 (2) | 0.058 (3) | 0.0079 (17) | 0.005 (2) | −0.002 (2) |
N1 | 0.048 (3) | 0.041 (3) | 0.050 (3) | 0.003 (2) | 0.007 (3) | 0.005 (3) |
N4 | 0.038 (2) | 0.026 (2) | 0.029 (3) | 0.004 (2) | −0.006 (2) | 0.002 (2) |
N10 | 0.041 (3) | 0.020 (2) | 0.043 (3) | −0.002 (2) | 0.008 (2) | 0.001 (2) |
C2 | 0.047 (3) | 0.028 (3) | 0.040 (4) | 0.005 (2) | 0.000 (3) | 0.003 (3) |
C3 | 0.041 (3) | 0.031 (3) | 0.032 (3) | 0.003 (2) | −0.003 (3) | 0.001 (2) |
C5 | 0.029 (3) | 0.032 (3) | 0.032 (3) | −0.005 (2) | 0.001 (3) | 0.011 (3) |
C6 | 0.028 (2) | 0.038 (3) | 0.028 (3) | −0.003 (2) | −0.001 (2) | 0.005 (3) |
C8 | 0.026 (3) | 0.039 (3) | 0.034 (3) | −0.004 (2) | −0.004 (3) | 0.004 (3) |
C9 | 0.034 (3) | 0.031 (3) | 0.044 (4) | 0.001 (2) | 0.014 (3) | 0.003 (3) |
C11 | 0.027 (3) | 0.035 (3) | 0.036 (3) | 0.008 (2) | 0.008 (3) | 0.011 (3) |
C12 | 0.057 (3) | 0.027 (3) | 0.053 (5) | 0.007 (3) | 0.019 (3) | 0.009 (3) |
C14 | 0.045 (3) | 0.022 (2) | 0.034 (3) | 0.003 (2) | 0.005 (3) | 0.008 (3) |
C15 | 0.069 (5) | 0.060 (4) | 0.062 (5) | −0.007 (4) | 0.009 (4) | 0.015 (4) |
C16 | 0.086 (6) | 0.083 (6) | 0.092 (8) | −0.018 (5) | −0.021 (6) | 0.036 (6) |
C17 | 0.065 (5) | 0.058 (5) | 0.146 (11) | 0.014 (4) | 0.047 (7) | 0.049 (6) |
C18 | 0.086 (6) | 0.036 (4) | 0.125 (9) | 0.007 (4) | 0.061 (6) | 0.005 (5) |
C19 | 0.070 (5) | 0.043 (4) | 0.063 (5) | −0.005 (3) | 0.023 (4) | 0.007 (4) |
C21 | 0.030 (3) | 0.043 (3) | 0.068 (5) | 0.003 (2) | 0.006 (3) | 0.016 (4) |
C22A | 0.039 (4) | 0.052 (5) | 0.086 (5) | 0.002 (4) | 0.022 (4) | −0.001 (4) |
C23A | 0.044 (4) | 0.051 (4) | 0.084 (5) | 0.001 (4) | 0.024 (4) | −0.003 (4) |
C24A | 0.046 (5) | 0.049 (4) | 0.080 (5) | 0.000 (4) | 0.025 (4) | −0.004 (4) |
C22B | 0.040 (4) | 0.051 (4) | 0.087 (5) | 0.000 (3) | 0.023 (4) | 0.000 (4) |
C23B | 0.041 (3) | 0.049 (4) | 0.082 (5) | 0.003 (3) | 0.023 (4) | −0.005 (4) |
C24B | 0.044 (4) | 0.049 (4) | 0.077 (5) | 0.000 (4) | 0.022 (4) | −0.006 (4) |
C26 | 0.027 (3) | 0.048 (3) | 0.025 (3) | −0.004 (2) | −0.001 (2) | −0.005 (3) |
C27 | 0.033 (3) | 0.044 (3) | 0.057 (4) | 0.005 (3) | −0.006 (3) | −0.016 (3) |
C28 | 0.037 (3) | 0.049 (4) | 0.069 (5) | 0.008 (3) | −0.014 (4) | −0.023 (4) |
C29 | 0.030 (3) | 0.080 (5) | 0.059 (5) | −0.002 (3) | −0.002 (3) | −0.028 (4) |
C30 | 0.051 (4) | 0.083 (5) | 0.064 (5) | −0.027 (4) | 0.000 (4) | 0.012 (5) |
C31 | 0.038 (3) | 0.071 (4) | 0.055 (5) | −0.014 (3) | −0.004 (3) | 0.020 (4) |
C33 | 0.057 (4) | 0.048 (3) | 0.031 (3) | 0.016 (3) | −0.012 (3) | −0.001 (3) |
C34 | 0.052 (4) | 0.097 (6) | 0.062 (5) | 0.013 (4) | −0.022 (4) | −0.005 (5) |
C35 | 0.046 (4) | 0.085 (5) | 0.066 (5) | −0.012 (4) | −0.006 (4) | −0.006 (5) |
C36 | 0.045 (3) | 0.039 (3) | 0.043 (4) | −0.009 (3) | −0.007 (3) | −0.008 (3) |
C38 | 0.078 (5) | 0.043 (4) | 0.062 (5) | −0.018 (3) | 0.025 (4) | −0.010 (4) |
C39 | 0.041 (3) | 0.074 (5) | 0.099 (7) | 0.008 (3) | 0.012 (4) | 0.005 (5) |
Geometric parameters (Å, º) top
O7—C8 | 1.352 (6) | C21—H214 | 0.9900 |
O7—C6 | 1.436 (6) | C22A—C23A | 1.529 (6) |
O13—C12 | 1.389 (7) | C22A—H221 | 0.9900 |
O13—H13 | 0.86 (2) | C22A—H222 | 0.9900 |
O20—C11 | 1.238 (6) | C23A—C24A | 1.533 (6) |
O25—C8 | 1.200 (6) | C23A—H231 | 0.9900 |
O32—C5 | 1.248 (6) | C23A—H232 | 0.9900 |
O37—C2 | 1.238 (6) | C24A—H241 | 0.9900 |
N1—C2 | 1.341 (7) | C24A—H242 | 0.9900 |
N1—C39 | 1.470 (7) | C22B—C23B | 1.526 (6) |
N1—C38 | 1.477 (7) | C22B—H223 | 0.9900 |
N4—C5 | 1.331 (7) | C22B—H224 | 0.9900 |
N4—C3 | 1.468 (7) | C23B—C24B | 1.529 (6) |
N4—H4 | 0.84 (2) | C23B—H233 | 0.9900 |
N10—C11 | 1.347 (8) | C23B—H234 | 0.9900 |
N10—C9 | 1.469 (7) | C24B—H243 | 0.9900 |
N10—H10 | 0.85 (2) | C24B—H244 | 0.9900 |
C2—C3 | 1.554 (8) | C26—C31 | 1.374 (8) |
C3—C36 | 1.533 (7) | C26—C27 | 1.387 (8) |
C3—C33 | 1.549 (8) | C27—C28 | 1.381 (8) |
C5—C6 | 1.528 (7) | C27—H27 | 0.9500 |
C6—C26 | 1.516 (7) | C28—C29 | 1.356 (9) |
C6—H6 | 1.0000 | C28—H28 | 0.9500 |
C8—C9 | 1.512 (7) | C29—C30 | 1.381 (10) |
C9—C24A | 1.529 (6) | C29—H29 | 0.9500 |
C9—C24B | 1.532 (6) | C30—C31 | 1.392 (8) |
C9—C21 | 1.575 (8) | C30—H30 | 0.9500 |
C11—C12 | 1.545 (7) | C31—H31 | 0.9500 |
C12—C14 | 1.516 (7) | C33—C34 | 1.528 (9) |
C12—H12 | 1.0000 | C33—H331 | 0.9900 |
C14—C15 | 1.347 (9) | C33—H332 | 0.9900 |
C14—C19 | 1.401 (9) | C34—C35 | 1.531 (11) |
C15—C16 | 1.400 (11) | C34—H341 | 0.9900 |
C15—H15 | 0.9500 | C34—H342 | 0.9900 |
C16—C17 | 1.379 (13) | C35—C36 | 1.524 (8) |
C16—H16 | 0.9500 | C35—H351 | 0.9900 |
C17—C18 | 1.387 (15) | C35—H352 | 0.9900 |
C17—H17 | 0.9500 | C36—H361 | 0.9900 |
C18—C19 | 1.384 (9) | C36—H362 | 0.9900 |
C18—H18 | 0.9500 | C38—H381 | 0.9800 |
C19—H19 | 0.9500 | C38—H382 | 0.9800 |
C21—C22B | 1.525 (6) | C38—H383 | 0.9800 |
C21—C22A | 1.530 (6) | C39—H391 | 0.9800 |
C21—H211 | 0.9900 | C39—H392 | 0.9800 |
C21—H212 | 0.9900 | C39—H393 | 0.9800 |
C21—H213 | 0.9900 | | |
| | | |
C8—O7—C6 | 115.3 (4) | H221—C22A—H222 | 108.8 |
C12—O13—H13 | 106 (5) | C22A—C23A—C24A | 108.5 (15) |
C2—N1—C39 | 116.6 (5) | C22A—C23A—H231 | 110.0 |
C2—N1—C38 | 127.4 (5) | C24A—C23A—H231 | 110.0 |
C39—N1—C38 | 115.8 (5) | C22A—C23A—H232 | 110.0 |
C5—N4—C3 | 121.9 (4) | C24A—C23A—H232 | 110.0 |
C5—N4—H4 | 121 (4) | H231—C23A—H232 | 108.4 |
C3—N4—H4 | 116 (4) | C9—C24A—C23A | 99.4 (11) |
C11—N10—C9 | 122.0 (4) | C9—C24A—H241 | 111.9 |
C11—N10—H10 | 122 (4) | C23A—C24A—H241 | 111.9 |
C9—N10—H10 | 116 (4) | C9—C24A—H242 | 111.9 |
O37—C2—N1 | 120.3 (5) | C23A—C24A—H242 | 111.9 |
O37—C2—C3 | 118.8 (5) | H241—C24A—H242 | 109.6 |
N1—C2—C3 | 120.8 (4) | C21—C22B—C23B | 101.3 (6) |
N4—C3—C36 | 111.0 (5) | C21—C22B—H223 | 111.5 |
N4—C3—C33 | 110.2 (4) | C23B—C22B—H223 | 111.5 |
C36—C3—C33 | 102.6 (4) | C21—C22B—H224 | 111.5 |
N4—C3—C2 | 110.6 (4) | C23B—C22B—H224 | 111.5 |
C36—C3—C2 | 111.8 (4) | H223—C22B—H224 | 109.3 |
C33—C3—C2 | 110.5 (5) | C22B—C23B—C24B | 103.6 (8) |
O32—C5—N4 | 122.8 (5) | C22B—C23B—H233 | 111.1 |
O32—C5—C6 | 118.4 (5) | C24B—C23B—H233 | 111.1 |
N4—C5—C6 | 118.8 (4) | C22B—C23B—H234 | 111.1 |
O7—C6—C26 | 109.0 (4) | C24B—C23B—H234 | 111.1 |
O7—C6—C5 | 111.6 (4) | H233—C23B—H234 | 109.0 |
C26—C6—C5 | 109.1 (4) | C23B—C24B—C9 | 107.4 (7) |
O7—C6—H6 | 109.0 | C23B—C24B—H243 | 110.2 |
C26—C6—H6 | 109.0 | C9—C24B—H243 | 110.2 |
C5—C6—H6 | 109.0 | C23B—C24B—H244 | 110.2 |
O25—C8—O7 | 122.2 (5) | C9—C24B—H244 | 110.2 |
O25—C8—C9 | 123.5 (4) | H243—C24B—H244 | 108.5 |
O7—C8—C9 | 114.3 (4) | C31—C26—C27 | 118.8 (5) |
N10—C9—C8 | 113.2 (4) | C31—C26—C6 | 122.6 (5) |
N10—C9—C24A | 109.1 (12) | C27—C26—C6 | 118.4 (5) |
C8—C9—C24A | 100.9 (12) | C28—C27—C26 | 120.6 (6) |
N10—C9—C24B | 110.0 (7) | C28—C27—H27 | 119.7 |
C8—C9—C24B | 114.7 (7) | C26—C27—H27 | 119.7 |
N10—C9—C21 | 109.7 (5) | C29—C28—C27 | 120.4 (6) |
C8—C9—C21 | 109.7 (4) | C29—C28—H28 | 119.8 |
C24A—C9—C21 | 114.0 (8) | C27—C28—H28 | 119.8 |
C24B—C9—C21 | 98.5 (5) | C28—C29—C30 | 119.9 (6) |
O20—C11—N10 | 123.5 (5) | C28—C29—H29 | 120.0 |
O20—C11—C12 | 119.3 (5) | C30—C29—H29 | 120.0 |
N10—C11—C12 | 117.3 (5) | C29—C30—C31 | 119.9 (7) |
O13—C12—C14 | 115.1 (5) | C29—C30—H30 | 120.0 |
O13—C12—C11 | 108.8 (5) | C31—C30—H30 | 120.0 |
C14—C12—C11 | 109.7 (4) | C26—C31—C30 | 120.3 (6) |
O13—C12—H12 | 107.7 | C26—C31—H31 | 119.9 |
C14—C12—H12 | 107.7 | C30—C31—H31 | 119.9 |
C11—C12—H12 | 107.7 | C34—C33—C3 | 106.3 (6) |
C15—C14—C19 | 119.2 (6) | C34—C33—H331 | 110.5 |
C15—C14—C12 | 120.9 (6) | C3—C33—H331 | 110.5 |
C19—C14—C12 | 119.9 (6) | C34—C33—H332 | 110.5 |
C14—C15—C16 | 121.3 (9) | C3—C33—H332 | 110.5 |
C14—C15—H15 | 119.3 | H331—C33—H332 | 108.7 |
C16—C15—H15 | 119.3 | C33—C34—C35 | 105.6 (5) |
C17—C16—C15 | 117.7 (9) | C33—C34—H341 | 110.6 |
C17—C16—H16 | 121.1 | C35—C34—H341 | 110.6 |
C15—C16—H16 | 121.1 | C33—C34—H342 | 110.6 |
C16—C17—C18 | 123.3 (8) | C35—C34—H342 | 110.6 |
C16—C17—H17 | 118.3 | H341—C34—H342 | 108.7 |
C18—C17—H17 | 118.3 | C36—C35—C34 | 105.6 (6) |
C19—C18—C17 | 116.2 (9) | C36—C35—H351 | 110.6 |
C19—C18—H18 | 121.9 | C34—C35—H351 | 110.6 |
C17—C18—H18 | 121.9 | C36—C35—H352 | 110.6 |
C18—C19—C14 | 122.2 (8) | C34—C35—H352 | 110.6 |
C18—C19—H19 | 118.9 | H351—C35—H352 | 108.8 |
C14—C19—H19 | 118.9 | C35—C36—C3 | 102.3 (5) |
C22B—C21—C9 | 112.6 (6) | C35—C36—H361 | 111.3 |
C22A—C21—C9 | 96.8 (10) | C3—C36—H361 | 111.3 |
C22A—C21—H211 | 112.4 | C35—C36—H362 | 111.3 |
C9—C21—H211 | 112.4 | C3—C36—H362 | 111.3 |
C22A—C21—H212 | 112.4 | H361—C36—H362 | 109.2 |
C9—C21—H212 | 112.4 | N1—C38—H381 | 109.5 |
H211—C21—H212 | 110.0 | N1—C38—H382 | 109.5 |
C22B—C21—H213 | 109.1 | H381—C38—H382 | 109.5 |
C9—C21—H213 | 109.1 | N1—C38—H383 | 109.5 |
C22B—C21—H214 | 109.1 | H381—C38—H383 | 109.5 |
C9—C21—H214 | 109.1 | H382—C38—H383 | 109.5 |
H213—C21—H214 | 107.8 | N1—C39—H391 | 109.5 |
C23A—C22A—C21 | 105.1 (13) | N1—C39—H392 | 109.5 |
C23A—C22A—H221 | 110.7 | H391—C39—H392 | 109.5 |
C21—C22A—H221 | 110.7 | N1—C39—H393 | 109.5 |
C23A—C22A—H222 | 110.7 | H391—C39—H393 | 109.5 |
C21—C22A—H222 | 110.7 | H392—C39—H393 | 109.5 |
| | | |
C39—N1—C2—O37 | 5.9 (10) | C12—C14—C15—C16 | 178.9 (6) |
C38—N1—C2—O37 | −179.3 (7) | C14—C15—C16—C17 | 0.4 (11) |
C39—N1—C2—C3 | −177.5 (6) | C15—C16—C17—C18 | −1.9 (13) |
C38—N1—C2—C3 | −2.7 (10) | C16—C17—C18—C19 | 2.2 (12) |
C5—N4—C3—C36 | −70.1 (6) | C17—C18—C19—C14 | −1.2 (10) |
C5—N4—C3—C33 | 177.0 (5) | C15—C14—C19—C18 | −0.2 (9) |
C5—N4—C3—C2 | 54.5 (6) | C12—C14—C19—C18 | −178.5 (6) |
O37—C2—C3—N4 | −135.0 (6) | N10—C9—C21—C22B | 106.9 (7) |
N1—C2—C3—N4 | 48.3 (7) | C8—C9—C21—C22B | −128.2 (7) |
O37—C2—C3—C36 | −10.8 (8) | C24B—C9—C21—C22B | −8.0 (10) |
N1—C2—C3—C36 | 172.5 (6) | N10—C9—C21—C22A | 94.7 (10) |
O37—C2—C3—C33 | 102.7 (6) | C8—C9—C21—C22A | −140.4 (10) |
N1—C2—C3—C33 | −73.9 (7) | C24A—C9—C21—C22A | −28.1 (17) |
C3—N4—C5—O32 | −3.5 (7) | C9—C21—C22A—C23A | 37.9 (17) |
C3—N4—C5—C6 | 179.7 (5) | C21—C22A—C23A—C24A | −39 (3) |
C8—O7—C6—C26 | 163.3 (5) | N10—C9—C24A—C23A | −116.8 (17) |
C8—O7—C6—C5 | −76.1 (5) | C8—C9—C24A—C23A | 123.8 (17) |
O32—C5—C6—O7 | 169.9 (4) | C21—C9—C24A—C23A | 6 (2) |
N4—C5—C6—O7 | −13.2 (6) | C22A—C23A—C24A—C9 | 19 (3) |
O32—C5—C6—C26 | −69.6 (6) | C9—C21—C22B—C23B | −16.6 (12) |
N4—C5—C6—C26 | 107.4 (5) | C21—C22B—C23B—C24B | 34.5 (13) |
C6—O7—C8—O25 | −2.8 (8) | C22B—C23B—C24B—C9 | −42.9 (14) |
C6—O7—C8—C9 | 179.8 (4) | N10—C9—C24B—C23B | −84.5 (10) |
C11—N10—C9—C8 | −64.2 (7) | C8—C9—C24B—C23B | 146.5 (8) |
C11—N10—C9—C24A | −175.7 (9) | C21—C9—C24B—C23B | 30.1 (10) |
C11—N10—C9—C24B | 166.0 (6) | O7—C6—C26—C31 | 25.7 (8) |
C11—N10—C9—C21 | 58.7 (6) | C5—C6—C26—C31 | −96.4 (6) |
O25—C8—C9—N10 | 166.8 (6) | O7—C6—C26—C27 | −158.4 (5) |
O7—C8—C9—N10 | −15.9 (7) | C5—C6—C26—C27 | 79.4 (6) |
O25—C8—C9—C24A | −76.7 (11) | C31—C26—C27—C28 | −0.7 (9) |
O7—C8—C9—C24A | 100.6 (10) | C6—C26—C27—C28 | −176.7 (6) |
O25—C8—C9—C24B | −65.8 (9) | C26—C27—C28—C29 | 0.7 (10) |
O7—C8—C9—C24B | 111.5 (7) | C27—C28—C29—C30 | 0.1 (10) |
O25—C8—C9—C21 | 43.9 (8) | C28—C29—C30—C31 | −0.9 (11) |
O7—C8—C9—C21 | −138.7 (5) | C27—C26—C31—C30 | −0.1 (10) |
C9—N10—C11—O20 | 8.9 (8) | C6—C26—C31—C30 | 175.8 (6) |
C9—N10—C11—C12 | −170.0 (5) | C29—C30—C31—C26 | 0.9 (12) |
O20—C11—C12—O13 | −163.6 (5) | N4—C3—C33—C34 | 88.4 (6) |
N10—C11—C12—O13 | 15.3 (7) | C36—C3—C33—C34 | −29.7 (6) |
O20—C11—C12—C14 | 69.7 (7) | C2—C3—C33—C34 | −149.0 (5) |
N10—C11—C12—C14 | −111.4 (6) | C3—C33—C34—C35 | 6.5 (7) |
O13—C12—C14—C15 | −34.0 (8) | C33—C34—C35—C36 | 19.6 (7) |
C11—C12—C14—C15 | 89.1 (6) | C34—C35—C36—C3 | −38.2 (7) |
O13—C12—C14—C19 | 144.3 (5) | N4—C3—C36—C35 | −76.3 (6) |
C11—C12—C14—C19 | −92.6 (7) | C33—C3—C36—C35 | 41.3 (6) |
C19—C14—C15—C16 | 0.6 (10) | C2—C3—C36—C35 | 159.7 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O32i | 0.86 (2) | 1.87 (3) | 2.713 (6) | 166 (8) |
N4—H4···O20 | 0.84 (2) | 2.09 (3) | 2.907 (5) | 164 (6) |
N10—H10···O37ii | 0.85 (2) | 2.17 (3) | 2.970 (6) | 155 (5) |
Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) −x+1/2, y−1/2, z−1/2. |
Hydrogen-bond geometry (Å, °) for (3b), (5a), (5b) and
(5c) topCompound | D—H···A | D—H | H···A | D···A | D—H···A |
(3b) | O19—H419···O45i | 0.84 | 2.11 | 2.814 (6) | 142 |
| N4—H4···O40 | 0.88 | 2.19 | 3.019 (7) | 156 |
| N10—H10···O27 | 0.88 | 2.07 | 3.882 (7) | 154 |
| N16—H16···O53i | 0.88 | 2.23 | 3.052 (6) | 156 |
(5a)† | O13—H13···O35ii | 0.90 (6) | 1.79 (6) | 2.670 (5) | 169 (5) |
| N4—H4···O21 | 0.90 (6) | 1.99 (6) | 2.881 (5) | 171 (5) |
| N10—H10···O53iii | 0.81 (5) | 2.36 (5) | 3.124 (5) | 157 (4) |
| O53—H53···O75iv | 0.86 (6) | 1.83 (6) | 2.684 (5) | 171 (6) |
| N44—H44···O61 | 0.85 (5) | 2.01 (5) | 2.824 (5) | 159 (5) |
| N50—H50···O13v | 0.84 (5) | 2.40 (5) | 3.185 (5) | 156 (4) |
(5b)‡ | O13—H131···O34vi | 0.84 | 2.00 | 2.753 (3) | 149 |
| O13—H132···O34vi | 0.84 | 1.92 | 2.753 (3) | 172 |
| N4—H4···O21 | 0.87 (3) | 2.06 (3) | 2.920 (3) | 170 (3) |
| N10—H10···O39vi | 0.84 (3) | 2.34 (3) | 3.161 (3) | 164 (3) |
(5c) | O13—H13···O32vii | 0.86 (2) | 1.87 (3) | 2.713 (6) | 166 (8) |
| N4—H4···O20 | 0.84 (2) | 2.09 (3) | 2.907 (5) | 164 (6) |
| N10—H10···O37viii | 0.85 (2) | 2.17 (3) | 2.970 (6) | 155 (5) |
Symmetry codes: (i) x, y, z-1;
(ii) -x+1, y-1/2, -z;
(iii) -x+1, y-1/2, -z+1;
(iv) -x, y+1/2, -z+1;
(v) -x+1, y+1/2, -z+1;
(vi) -x+1/2, y+1/2, -z+1/2;
(vii) -x+1/2, y-1/2, z+1/2;
(viii) -x+1/2, y-1/2, z-1/2.
† Two symmetry-independent molecules; the atom numbers of molecule
B correspond with those of molecule A + 40.
‡ The hydroxy group is disordered. |
Torsion angles ω, φ and ψ (°) of the backbone of the depsipeptide
molecules in the structures of (3b), (5a), (5b) and
(5c) topCompound | Amino/hydroxy acid† | | Atoms | Torsion angles |
(3b) | Pms(1) | ψ1 | O19—C18—C17—N16 | -9.6 (9) |
| | ω1 | C18—C17—N16—C15 | 179.0 (6) |
| Acp(2)' | φ2 | C17—N16—C15—C14 | -49.1 (8) |
| | ψ2 | N16—C15—C14—O13 | -34.2 (7) |
| | w2 | C15—C14—O13—C12 | -171.3 (5) |
| Pms(3) | φ3 | C14—O13—C12—C11 | -77.1 (6) |
| | ψ3 | O13—C12—C11—N10 | -17.0 (8) |
| | ω3 | C12—C11—N10—C9 | 179.0 (5) |
| Acp(4) | φ4 | C11—N10—C9—C8 | -49.7 (7) |
| | ψ4 | N10—C9—C8—O7 | -35.2 (7) |
| | ω4 | C9—C8—O7—C6 | -167.0 (5) |
| Pms(5) | φ5 | C8—O7—C6—C5 | -93.5 (6) |
| | ψ5 | O7—C6—C5—N4 | -5.5 (7) |
| | ω5 | C6—C5—N4—C3 | 178.9 (6) |
| Acp(6) | φ6 | C5—N4—C3—C2 | 51.6 (8) |
| | ψ6 | N4—C3—C2—N1 | 43.6 (10) |
| | | | |
(5a)‡ | Pms(1) | ψ1 | O13—C12—C11—N10 | -18.9 (6); -17.2 (5) |
| | ω1 | C12—C11—N10—C9 | -173.3 (4); -171.1 (4) |
| Aib(2) | φ2 | C11—N10—C9—C8 | -51.5 (6); -50.9 (6) |
| | ψ2 | N10—C9—C8—O7 | -33.1 (6); -33.8 (6) |
| | ω2 | C9—C8—O7—C6 | -169.9 (3); -173.1 (4) |
| Pms(3) | φ3 | C8—O7—C6—C5 | -98.6 (4); -96.0 (5) |
| | ψ3 | O7—C6—C5—N4 | -2.1 (6); -6.9 (6) |
| | ω3 | C6—C5—N4—C3 | 178.5 (4); -179.4 (4) |
| Aib(4) | ?4 | C5—N4—C3—C2 | -48.8 (6); -49.1 (5) |
| | ?4 | N4—C3—C2—N1 | -43.2 (6); -44.3 (5) |
| | | | |
(5b) | Pms(1) | ψ1 | O13—C12a—C11—N10§ | 22.1 (8) |
| | | O13—C12b—C11—N10§§ | -13.0 (8) |
| | ω1 | C12a—C11—N10—C9§ | 166.4 (4) |
| | | C12b—C11—N10—C9§§ | -174.9 (4) |
| Acp(2) | φ2 | C11—N10—C9—C8 | 51.3 (4) |
| | ψ2 | N10—C9—C8—O7 | 37.3 (3) |
| | ω2 | C9—C8—O7—C6 | 169.0 (2) |
| Pms(3) | φ3 | C8—O7—C6—C5 | 84.6 (3) |
| | ψ3 | O7—C6—C5—N4 | 2.5 (4) |
| | ω3 | C6—C5—N4—C3 | 175.7 (2) |
| Acp(4) | φ4 | C5—N4—C3—C2 | 46.8 (3) |
| | ψ4 | N4—C3—C2—N1 | 54.9 (3) |
| | | | |
(5c) | Mns(1) | ψ1 | O13—C12—C11—N10 | 15.3 (7) |
| | ω1 | C12—C11—N10—C9 | -170.0 (5) |
| Acp(2) | φ2 | C11—N10—C9—C8 | -64.2 (7) |
| | ψ2 | N10—C9—C8—O7 | -15.9 (7) |
| | ω2 | C9—C8—O7—C6 | 179.8 (4) |
| Mns(3) | φ3 | C8—O7—C6—C5 | -76.1 (5) |
| | ψ3 | O7—C6—C5—N4 | -13.2 (6) |
| | ω3 | C6—C5—N4—C3 | 179.7 (5) |
| Acp(4) | φ4 | C5—N4—C3—C2 | 54.5 (6) |
| | ψ4 | N4—C3—C2—N1 | 48.3 (7) |
Notes: Acp is 1-aminocyclopentane carboxylic acid, Pms is phenyllactic acid, Aib
is aminoisobutyric acid and Mns is mandelic acid.
‡ Two symmetry-independent molecules. The atom numbers for molecule
A are given and those of molecule B are obtained by adding 40;
the torsion angles for molecule B are listed second.
§ S,R-isomer.
§§ R,R-isomer. |