Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027030/hg6235sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027030/hg6235Isup2.hkl |
CCDC reference: 285510
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C22H29NO3 | Dx = 1.230 Mg m−3 |
Mr = 355.46 | Melting point: 568 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1995 reflections |
a = 6.2505 (2) Å | θ = 2.0–25.0° |
b = 13.3718 (4) Å | µ = 0.08 mm−1 |
c = 22.9703 (7) Å | T = 160 K |
V = 1919.87 (10) Å3 | Prism, colourless |
Z = 4 | 0.18 × 0.13 × 0.05 mm |
F(000) = 768 |
Nonius KappaCCD area-detector diffractometer | 1601 reflections with I > 2σ(I) |
Radiation source: Nonius FR590 sealed-tube generator | Rint = 0.069 |
Horizontally mounted graphite crystal monochromator | θmax = 25.0°, θmin = 2.3° |
Detector resolution: 9 pixels mm-1 | h = −7→7 |
φ and ω scans with κ offsets | k = −15→15 |
20155 measured reflections | l = −27→27 |
1982 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom & difmap |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0677P)2 + 0.1751P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
1979 reflections | Δρmax = 0.24 e Å−3 |
241 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Absolute structure: Flack & Bernardinelli (2000) |
Primary atom site location: structure-invariant direct methods |
Experimental. Solvent used: Methanol Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.462 (2) Frames collected: 255 Seconds exposure per frame: 135 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 35.0 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O16 | −0.1065 (4) | 0.45481 (14) | 0.16626 (9) | 0.0475 (6) | |
O17A | 0.4612 (3) | 0.29720 (15) | 0.08657 (8) | 0.0412 (6) | |
O31 | −0.3509 (4) | −0.37628 (16) | 0.19240 (10) | 0.0495 (7) | |
H31 | −0.279 (6) | −0.422 (2) | 0.1800 (14) | 0.050 (11)* | |
C1 | 0.0490 (5) | −0.1902 (2) | 0.14993 (12) | 0.0358 (7) | |
H1 | 0.1836 | −0.1872 | 0.1308 | 0.043* | |
C2 | −0.0494 (5) | −0.2818 (2) | 0.15617 (12) | 0.0385 (8) | |
H2 | 0.0166 | −0.3406 | 0.1414 | 0.046* | |
C3 | −0.2440 (5) | −0.2875 (2) | 0.18398 (12) | 0.0347 (7) | |
C4 | −0.3356 (5) | −0.2018 (2) | 0.20562 (11) | 0.0337 (7) | |
H4 | −0.4693 | −0.2060 | 0.2252 | 0.040* | |
C5 | −0.2373 (5) | −0.10905 (19) | 0.19960 (11) | 0.0288 (7) | |
C6 | −0.3479 (5) | −0.01832 (19) | 0.22413 (13) | 0.0359 (7) | |
H61 | −0.3968 | −0.0338 | 0.2641 | 0.043* | |
H62 | −0.4763 | −0.0041 | 0.2003 | 0.043* | |
C7 | −0.2095 (5) | 0.0749 (2) | 0.22607 (12) | 0.0344 (7) | |
H71 | −0.1073 | 0.0699 | 0.2589 | 0.041* | |
H72 | −0.3008 | 0.1343 | 0.2326 | 0.041* | |
C8 | −0.0868 (5) | 0.08689 (19) | 0.16919 (11) | 0.0291 (7) | |
H8 | −0.1918 | 0.0839 | 0.1364 | 0.035* | |
C9 | 0.0696 (5) | −0.00104 (19) | 0.16252 (11) | 0.0308 (7) | |
H9 | 0.1773 | 0.0052 | 0.1945 | 0.037* | |
C10 | −0.0417 (5) | −0.1018 (2) | 0.17067 (11) | 0.0307 (7) | |
C11 | 0.1921 (6) | 0.0069 (2) | 0.10519 (13) | 0.0421 (8) | |
H111 | 0.0911 | −0.0023 | 0.0724 | 0.051* | |
H112 | 0.2995 | −0.0474 | 0.1033 | 0.051* | |
C12 | 0.3052 (5) | 0.10757 (19) | 0.09841 (13) | 0.0385 (8) | |
H121 | 0.3710 | 0.1111 | 0.0593 | 0.046* | |
H122 | 0.4213 | 0.1124 | 0.1276 | 0.046* | |
C13 | 0.1523 (5) | 0.19641 (19) | 0.10620 (11) | 0.0298 (6) | |
C14 | 0.0346 (4) | 0.18645 (19) | 0.16495 (11) | 0.0288 (6) | |
H14 | 0.1462 | 0.1860 | 0.1961 | 0.035* | |
C15 | −0.1060 (5) | 0.27827 (19) | 0.17533 (12) | 0.0354 (7) | |
H151 | −0.2436 | 0.2680 | 0.1548 | 0.043* | |
H152 | −0.1378 | 0.2825 | 0.2175 | 0.043* | |
C16 | −0.0147 (5) | 0.3761 (2) | 0.15624 (12) | 0.0364 (7) | |
N17 | 0.1804 (4) | 0.37790 (16) | 0.12762 (9) | 0.0356 (6) | |
C17A | 0.2816 (5) | 0.2916 (2) | 0.10650 (11) | 0.0328 (7) | |
C18 | −0.0027 (5) | 0.2053 (2) | 0.05406 (12) | 0.0420 (8) | |
H181 | −0.0954 | 0.2636 | 0.0595 | 0.063* | |
H182 | −0.0905 | 0.1447 | 0.0516 | 0.063* | |
H183 | 0.0797 | 0.2131 | 0.0180 | 0.063* | |
C19 | 0.2788 (6) | 0.4744 (2) | 0.11138 (13) | 0.0469 (9) | |
H191 | 0.4357 | 0.4660 | 0.1079 | 0.056* | |
H192 | 0.2507 | 0.5243 | 0.1423 | 0.056* | |
C20 | 0.1890 (7) | 0.5126 (2) | 0.05363 (13) | 0.0521 (9) | |
H201 | 0.2061 | 0.4600 | 0.0237 | 0.063* | |
H202 | 0.0340 | 0.5257 | 0.0582 | 0.063* | |
C21 | 0.2985 (7) | 0.6078 (2) | 0.03274 (14) | 0.0640 (12) | |
H211 | 0.4506 | 0.5934 | 0.0242 | 0.077* | |
H212 | 0.2934 | 0.6587 | 0.0640 | 0.077* | |
C22 | 0.1906 (9) | 0.6494 (3) | −0.02190 (18) | 0.0913 (16) | |
H221 | 0.1964 | 0.5993 | −0.0530 | 0.137* | |
H222 | 0.2654 | 0.7101 | −0.0345 | 0.137* | |
H223 | 0.0410 | 0.6655 | −0.0132 | 0.137* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O16 | 0.0525 (15) | 0.0323 (12) | 0.0577 (14) | 0.0028 (11) | 0.0100 (12) | −0.0045 (10) |
O17A | 0.0370 (14) | 0.0431 (12) | 0.0434 (12) | −0.0040 (11) | 0.0033 (11) | 0.0046 (9) |
O31 | 0.0517 (16) | 0.0308 (12) | 0.0662 (15) | −0.0022 (12) | 0.0152 (13) | −0.0008 (11) |
C1 | 0.0336 (18) | 0.0324 (15) | 0.0413 (16) | 0.0032 (14) | 0.0086 (15) | 0.0003 (12) |
C2 | 0.046 (2) | 0.0281 (15) | 0.0410 (16) | 0.0071 (14) | 0.0078 (16) | 0.0008 (12) |
C3 | 0.0393 (19) | 0.0296 (15) | 0.0352 (16) | −0.0003 (14) | 0.0016 (14) | 0.0018 (12) |
C4 | 0.0291 (17) | 0.0363 (16) | 0.0356 (15) | 0.0020 (15) | 0.0040 (14) | 0.0034 (13) |
C5 | 0.0283 (17) | 0.0271 (15) | 0.0311 (14) | 0.0005 (13) | −0.0018 (13) | 0.0018 (11) |
C6 | 0.0339 (17) | 0.0333 (15) | 0.0405 (16) | 0.0046 (14) | 0.0084 (15) | 0.0019 (12) |
C7 | 0.0353 (18) | 0.0302 (15) | 0.0378 (15) | −0.0002 (14) | 0.0080 (14) | −0.0021 (12) |
C8 | 0.0287 (17) | 0.0279 (14) | 0.0308 (13) | 0.0002 (12) | 0.0005 (13) | −0.0008 (12) |
C9 | 0.0267 (16) | 0.0307 (15) | 0.0351 (15) | 0.0011 (13) | 0.0037 (13) | −0.0005 (12) |
C10 | 0.0305 (17) | 0.0304 (14) | 0.0312 (14) | 0.0034 (13) | 0.0021 (14) | 0.0033 (12) |
C11 | 0.044 (2) | 0.0315 (15) | 0.0505 (17) | 0.0024 (15) | 0.0166 (17) | −0.0037 (14) |
C12 | 0.038 (2) | 0.0346 (16) | 0.0431 (16) | 0.0005 (14) | 0.0123 (15) | 0.0012 (13) |
C13 | 0.0304 (16) | 0.0301 (14) | 0.0289 (13) | 0.0019 (14) | 0.0024 (13) | −0.0006 (12) |
C14 | 0.0249 (15) | 0.0316 (14) | 0.0300 (13) | 0.0018 (12) | 0.0013 (13) | −0.0014 (11) |
C15 | 0.0370 (18) | 0.0332 (15) | 0.0360 (15) | 0.0028 (14) | 0.0027 (14) | −0.0022 (13) |
C16 | 0.043 (2) | 0.0320 (16) | 0.0338 (15) | −0.0006 (15) | −0.0025 (15) | −0.0038 (12) |
N17 | 0.0401 (16) | 0.0293 (12) | 0.0373 (13) | −0.0052 (12) | 0.0018 (13) | −0.0007 (10) |
C17A | 0.0343 (19) | 0.0380 (16) | 0.0262 (14) | 0.0005 (15) | −0.0036 (14) | 0.0033 (12) |
C18 | 0.0444 (19) | 0.0491 (18) | 0.0325 (14) | −0.0063 (17) | −0.0013 (15) | 0.0006 (13) |
C19 | 0.053 (2) | 0.0405 (18) | 0.0469 (18) | −0.0041 (16) | 0.0081 (18) | −0.0061 (14) |
C20 | 0.066 (3) | 0.0400 (17) | 0.0504 (18) | −0.0021 (18) | 0.0098 (19) | −0.0001 (14) |
C21 | 0.088 (3) | 0.047 (2) | 0.058 (2) | −0.004 (2) | 0.024 (2) | 0.0038 (17) |
C22 | 0.116 (4) | 0.076 (3) | 0.081 (3) | 0.005 (3) | 0.025 (3) | 0.032 (2) |
O16—C16 | 1.220 (3) | C12—C13 | 1.535 (4) |
O17A—C17A | 1.215 (3) | C12—H121 | 0.9900 |
O31—C3 | 1.376 (3) | C12—H122 | 0.9900 |
O31—H31 | 0.81 (3) | C13—C17A | 1.508 (4) |
C1—C2 | 1.378 (4) | C13—C14 | 1.543 (4) |
C1—C10 | 1.395 (4) | C13—C18 | 1.545 (4) |
C1—H1 | 0.9500 | C14—C15 | 1.529 (4) |
C2—C3 | 1.376 (4) | C14—H14 | 1.0000 |
C2—H2 | 0.9500 | C15—C16 | 1.494 (4) |
C3—C4 | 1.374 (4) | C15—H151 | 0.9900 |
C4—C5 | 1.391 (4) | C15—H152 | 0.9900 |
C4—H4 | 0.9500 | C16—N17 | 1.385 (4) |
C5—C10 | 1.395 (4) | N17—C17A | 1.403 (4) |
C5—C6 | 1.506 (4) | N17—C19 | 1.478 (4) |
C6—C7 | 1.518 (4) | C18—H181 | 0.9800 |
C6—H61 | 0.9900 | C18—H182 | 0.9800 |
C6—H62 | 0.9900 | C18—H183 | 0.9800 |
C7—C8 | 1.523 (4) | C19—C20 | 1.528 (5) |
C7—H71 | 0.9900 | C19—H191 | 0.9900 |
C7—H72 | 0.9900 | C19—H192 | 0.9900 |
C8—C14 | 1.535 (4) | C20—C21 | 1.523 (5) |
C8—C9 | 1.537 (4) | C20—H201 | 0.9900 |
C8—H8 | 1.0000 | C20—H202 | 0.9900 |
C9—C11 | 1.527 (4) | C21—C22 | 1.529 (6) |
C9—C10 | 1.528 (4) | C21—H211 | 0.9900 |
C9—H9 | 1.0000 | C21—H212 | 0.9900 |
C11—C12 | 1.528 (4) | C22—H221 | 0.9800 |
C11—H111 | 0.9900 | C22—H222 | 0.9800 |
C11—H112 | 0.9900 | C22—H223 | 0.9800 |
C3—O31—H31 | 109 (2) | C17A—C13—C14 | 108.9 (2) |
C2—C1—C10 | 122.4 (3) | C12—C13—C14 | 109.4 (2) |
C2—C1—H1 | 118.8 | C17A—C13—C18 | 106.0 (2) |
C10—C1—H1 | 118.8 | C12—C13—C18 | 111.0 (2) |
C3—C2—C1 | 119.5 (3) | C14—C13—C18 | 112.7 (2) |
C3—C2—H2 | 120.3 | C15—C14—C8 | 113.7 (2) |
C1—C2—H2 | 120.3 | C15—C14—C13 | 110.0 (2) |
C4—C3—C2 | 119.4 (3) | C8—C14—C13 | 111.5 (2) |
C4—C3—O31 | 117.8 (3) | C15—C14—H14 | 107.1 |
C2—C3—O31 | 122.8 (3) | C8—C14—H14 | 107.1 |
C3—C4—C5 | 121.5 (3) | C13—C14—H14 | 107.1 |
C3—C4—H4 | 119.2 | C16—C15—C14 | 116.0 (2) |
C5—C4—H4 | 119.2 | C16—C15—H151 | 108.3 |
C4—C5—C10 | 119.8 (2) | C14—C15—H151 | 108.3 |
C4—C5—C6 | 118.6 (2) | C16—C15—H152 | 108.3 |
C10—C5—C6 | 121.7 (2) | C14—C15—H152 | 108.3 |
C5—C6—C7 | 114.3 (2) | H151—C15—H152 | 107.4 |
C5—C6—H61 | 108.7 | O16—C16—N17 | 119.3 (3) |
C7—C6—H61 | 108.7 | O16—C16—C15 | 121.3 (3) |
C5—C6—H62 | 108.7 | N17—C16—C15 | 119.4 (3) |
C7—C6—H62 | 108.7 | C16—N17—C17A | 123.2 (2) |
H61—C6—H62 | 107.6 | C16—N17—C19 | 120.1 (2) |
C6—C7—C8 | 110.4 (2) | C17A—N17—C19 | 116.3 (2) |
C6—C7—H71 | 109.6 | O17A—C17A—N17 | 119.7 (3) |
C8—C7—H71 | 109.6 | O17A—C17A—C13 | 123.1 (3) |
C6—C7—H72 | 109.6 | N17—C17A—C13 | 117.0 (2) |
C8—C7—H72 | 109.6 | C13—C18—H181 | 109.5 |
H71—C7—H72 | 108.1 | C13—C18—H182 | 109.5 |
C7—C8—C14 | 113.2 (2) | H181—C18—H182 | 109.5 |
C7—C8—C9 | 109.0 (2) | C13—C18—H183 | 109.5 |
C14—C8—C9 | 110.0 (2) | H181—C18—H183 | 109.5 |
C7—C8—H8 | 108.2 | H182—C18—H183 | 109.5 |
C14—C8—H8 | 108.2 | N17—C19—C20 | 111.0 (3) |
C9—C8—H8 | 108.2 | N17—C19—H191 | 109.4 |
C11—C9—C10 | 113.3 (2) | C20—C19—H191 | 109.4 |
C11—C9—C8 | 110.6 (2) | N17—C19—H192 | 109.4 |
C10—C9—C8 | 111.9 (2) | C20—C19—H192 | 109.4 |
C11—C9—H9 | 106.9 | H191—C19—H192 | 108.0 |
C10—C9—H9 | 106.9 | C21—C20—C19 | 112.8 (3) |
C8—C9—H9 | 106.9 | C21—C20—H201 | 109.0 |
C5—C10—C1 | 117.4 (2) | C19—C20—H201 | 109.0 |
C5—C10—C9 | 121.3 (2) | C21—C20—H202 | 109.0 |
C1—C10—C9 | 121.4 (2) | C19—C20—H202 | 109.0 |
C9—C11—C12 | 112.4 (2) | H201—C20—H202 | 107.8 |
C9—C11—H111 | 109.1 | C20—C21—C22 | 111.4 (4) |
C12—C11—H111 | 109.1 | C20—C21—H211 | 109.4 |
C9—C11—H112 | 109.1 | C22—C21—H211 | 109.4 |
C12—C11—H112 | 109.1 | C20—C21—H212 | 109.4 |
H111—C11—H112 | 107.9 | C22—C21—H212 | 109.4 |
C11—C12—C13 | 112.4 (2) | H211—C21—H212 | 108.0 |
C11—C12—H121 | 109.1 | C21—C22—H221 | 109.5 |
C13—C12—H121 | 109.1 | C21—C22—H222 | 109.5 |
C11—C12—H122 | 109.1 | H221—C22—H222 | 109.5 |
C13—C12—H122 | 109.1 | C21—C22—H223 | 109.5 |
H121—C12—H122 | 107.8 | H221—C22—H223 | 109.5 |
C17A—C13—C12 | 108.7 (2) | H222—C22—H223 | 109.5 |
C10—C1—C2—C3 | −0.3 (4) | C7—C8—C14—C15 | −53.8 (3) |
C1—C2—C3—C4 | −0.7 (4) | C9—C8—C14—C15 | −176.0 (2) |
C1—C2—C3—O31 | −179.3 (3) | C7—C8—C14—C13 | −178.8 (2) |
C2—C3—C4—C5 | 0.6 (4) | C9—C8—C14—C13 | 59.0 (3) |
O31—C3—C4—C5 | 179.3 (2) | C17A—C13—C14—C15 | 57.2 (3) |
C3—C4—C5—C10 | 0.4 (4) | C12—C13—C14—C15 | 175.9 (2) |
C3—C4—C5—C6 | 179.6 (3) | C18—C13—C14—C15 | −60.1 (3) |
C4—C5—C6—C7 | 168.5 (2) | C17A—C13—C14—C8 | −175.7 (2) |
C10—C5—C6—C7 | −12.3 (4) | C12—C13—C14—C8 | −57.0 (3) |
C5—C6—C7—C8 | 44.4 (3) | C18—C13—C14—C8 | 67.0 (3) |
C6—C7—C8—C14 | 172.7 (2) | C8—C14—C15—C16 | −164.0 (2) |
C6—C7—C8—C9 | −64.5 (3) | C13—C14—C15—C16 | −38.2 (3) |
C7—C8—C9—C11 | 178.6 (2) | C14—C15—C16—O16 | −174.6 (3) |
C14—C8—C9—C11 | −56.7 (3) | C14—C15—C16—N17 | 4.0 (4) |
C7—C8—C9—C10 | 51.3 (3) | O16—C16—N17—C17A | −170.0 (3) |
C14—C8—C9—C10 | 176.0 (2) | C15—C16—N17—C17A | 11.3 (4) |
C4—C5—C10—C1 | −1.3 (4) | O16—C16—N17—C19 | 2.1 (4) |
C6—C5—C10—C1 | 179.5 (3) | C15—C16—N17—C19 | −176.6 (3) |
C4—C5—C10—C9 | 179.2 (2) | C16—N17—C17A—O17A | −173.3 (2) |
C6—C5—C10—C9 | 0.0 (4) | C19—N17—C17A—O17A | 14.3 (4) |
C2—C1—C10—C5 | 1.3 (4) | C16—N17—C17A—C13 | 10.8 (4) |
C2—C1—C10—C9 | −179.3 (3) | C19—N17—C17A—C13 | −161.7 (3) |
C11—C9—C10—C5 | −145.9 (3) | C12—C13—C17A—O17A | 19.9 (3) |
C8—C9—C10—C5 | −20.0 (3) | C14—C13—C17A—O17A | 139.1 (3) |
C11—C9—C10—C1 | 34.7 (4) | C18—C13—C17A—O17A | −99.5 (3) |
C8—C9—C10—C1 | 160.5 (3) | C12—C13—C17A—N17 | −164.3 (2) |
C10—C9—C11—C12 | −179.0 (3) | C14—C13—C17A—N17 | −45.2 (3) |
C8—C9—C11—C12 | 54.5 (3) | C18—C13—C17A—N17 | 76.3 (3) |
C9—C11—C12—C13 | −53.9 (3) | C16—N17—C19—C20 | −83.9 (3) |
C11—C12—C13—C17A | 172.8 (2) | C17A—N17—C19—C20 | 88.7 (3) |
C11—C12—C13—C14 | 54.0 (3) | N17—C19—C20—C21 | −175.4 (3) |
C11—C12—C13—C18 | −71.0 (3) | C19—C20—C21—C22 | −174.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O31—H31···O16i | 0.81 (3) | 2.00 (3) | 2.792 (3) | 168 (3) |
C15—H151···O17Aii | 0.99 | 2.45 | 3.397 (4) | 159 |
C18—H183···O17Aiii | 0.98 | 2.52 | 3.238 (3) | 130 |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, −z. |