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The crystal structure of the title compound, C21H18N2O3, reveals an inter­esting case of axial conformational chirality. Due to the symmetry requirements of the space group (P21/n), conformational stereoisomers of both P and M helicity are present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020125/cs2005sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020125/cs2005Isup2.hkl
Contains datablock I

CCDC reference: 613642

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.110
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 .. 5.99 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1N ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. O1 .. 2.65 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

phenyl N-[2-(acetylamino)biphenyl-4-yl]carbamate top
Crystal data top
C21H18N2O3F(000) = 728
Mr = 346.37Dx = 1.275 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 11.260 (13) ÅCell parameters from 25 reflections
b = 12.74 (2) Åθ = 8–17°
c = 12.81 (2) ŵ = 0.7 mm1
β = 100.76 (13)°T = 293 K
V = 1805 (5) Å3Prism, colourless
Z = 40.32 × 0.3 × 0.2 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
θmax = 76.5°, θmin = 4.9°
non–profiled ω/2θ scansh = 1414
7498 measured reflectionsk = 016
3756 independent reflectionsl = 1616
2854 reflections with I > 2σ(I)3 standard reflections every 120 min
Rint = 0.031 intensity decay: 1%
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0506P)2 + 0.2871P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.039(Δ/σ)max < 0.001
wR(F2) = 0.110Δρmax = 0.24 e Å3
S = 1.02Δρmin = 0.28 e Å3
3756 reflectionsExtinction correction: SHELXS97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
296 parametersExtinction coefficient: 0.0032 (4)
0 restraints
Special details top

Experimental. Spectroscopic analysis: 1H NMR (DMSO-d6, δ, p.p.m.): 1.83 (s, CH3, 3H), 7.16–7.28 (m, BiPhe, 5H, Phe, 3H), 7.36–7.40 (m, BiPhe, 1H, Phe, 2H), 7.50–7.51 (BiPhe, 2H), 9.15 (s, NHCOCH3, 1H), 10.27 (s, NH, 1H); 13C NMR (DMSO-d6, δ, p.p.m.): 23.02 (CH3), 118.40, 121.85, 125.39, 125.77, 127.03, 127.34, 129.20, 129.40, 130.05, 133.59, 134.89, 136.07, 137.73, 150.53, 151.70, 168.57; IR (KBr, ν, cm-1): 3454.26, 3394.47, 3238.24, 3172.67, 3093.59, 3041.52, 2937.37, 2856.37, 2790.79, 2362.63, 2335.62, 2219.90, 1951.82, 1930.60, 1733.88, 1666.37, 1608.51, 1589.23, 1483.15, 1446.51, 1407.93, 1321.14, 1298.00, 1228.57, 1157.20, 1068.49, 1022.20, 1010.63, 916.20, 835.12, 811.97, 796.54, 756.04, 719.40, 663.46, 561.24, 507.24, 466.74, 379.95, 329.80, 287.37.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.31521 (14)0.46781 (14)0.88579 (13)0.0580 (4)
C20.19798 (13)0.42740 (11)0.82207 (11)0.0461 (3)
C30.08911 (12)0.38805 (11)0.64074 (10)0.0439 (3)
C40.02684 (14)0.42802 (14)0.63844 (13)0.0562 (4)
C50.12322 (15)0.39400 (16)0.56271 (15)0.0683 (5)
C60.10448 (16)0.32182 (18)0.48750 (15)0.0728 (5)
C70.01107 (15)0.28208 (15)0.48943 (13)0.0604 (4)
C80.10982 (12)0.31247 (11)0.56694 (10)0.0439 (3)
C90.23102 (12)0.26326 (11)0.57023 (10)0.0420 (3)
C100.27938 (13)0.25041 (12)0.47827 (11)0.0491 (3)
C110.39088 (13)0.20179 (13)0.48166 (10)0.0487 (3)
C120.45839 (12)0.16628 (11)0.57723 (10)0.0429 (3)
C130.41005 (12)0.17648 (12)0.66959 (10)0.0450 (3)
C140.29829 (13)0.22417 (11)0.66496 (10)0.0443 (3)
C150.66316 (13)0.11177 (13)0.66091 (11)0.0487 (3)
C160.86395 (13)0.05460 (13)0.71359 (11)0.0494 (3)
C170.88001 (18)0.04234 (16)0.76027 (15)0.0660 (4)
C180.9781 (2)0.0575 (2)0.84284 (17)0.0798 (6)
C191.05668 (18)0.0220 (2)0.87639 (15)0.0776 (6)
C201.04112 (16)0.1173 (2)0.82793 (17)0.0751 (6)
C210.94430 (16)0.13453 (15)0.74553 (15)0.0618 (4)
H1A0.36740.48940.83840.087*0.5
H1B0.35380.41320.93160.087*0.5
H1C0.29920.52660.9280.087*0.5
H1D0.31280.46340.96020.087*0.5
H1E0.32640.53960.86710.087*0.5
H1F0.3810.42620.87070.087*0.5
H1N0.2553 (19)0.4464 (15)0.6900 (16)0.077 (6)*
H2N0.5943 (17)0.1095 (15)0.5116 (16)0.071 (5)*
H40.0367 (16)0.4793 (14)0.6935 (15)0.065 (5)*
H50.206 (2)0.4229 (16)0.5595 (17)0.085 (6)*
H60.1740 (19)0.2979 (16)0.4354 (17)0.085 (6)*
H70.0244 (17)0.2282 (15)0.4355 (16)0.075 (5)*
H100.2302 (14)0.2756 (13)0.4099 (14)0.056 (4)*
H110.4230 (14)0.1945 (13)0.4167 (14)0.056 (4)*
H130.4549 (14)0.1530 (12)0.7374 (13)0.048 (4)*
H140.2654 (14)0.2303 (12)0.7326 (13)0.054 (4)*
H170.8264 (19)0.0942 (19)0.7374 (17)0.088 (7)*
H180.990 (2)0.120 (2)0.8746 (19)0.102 (8)*
H191.128 (2)0.0093 (17)0.9387 (18)0.088 (6)*
H201.100 (2)0.175 (2)0.856 (2)0.117 (9)*
H210.934 (2)0.2006 (19)0.7127 (19)0.099 (7)*
N10.18901 (11)0.42823 (10)0.71585 (9)0.0472 (3)
N20.57348 (11)0.12143 (11)0.57576 (9)0.0520 (3)
O10.11529 (11)0.39476 (12)0.86327 (9)0.0741 (4)
O20.65950 (10)0.13264 (12)0.75166 (8)0.0693 (4)
O30.76480 (10)0.07135 (11)0.63069 (8)0.0671 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0528 (9)0.0687 (10)0.0506 (8)0.0058 (7)0.0047 (7)0.0023 (7)
C20.0487 (7)0.0491 (8)0.0416 (7)0.0015 (6)0.0114 (6)0.0019 (6)
C30.0443 (7)0.0497 (7)0.0385 (6)0.0003 (6)0.0094 (5)0.0026 (6)
C40.0518 (8)0.0631 (10)0.0552 (9)0.0104 (7)0.0134 (7)0.0016 (7)
C50.0463 (9)0.0891 (13)0.0663 (10)0.0199 (9)0.0028 (7)0.0008 (9)
C60.0496 (9)0.1016 (15)0.0592 (10)0.0129 (9)0.0104 (8)0.0096 (10)
C70.0530 (9)0.0765 (11)0.0474 (8)0.0100 (8)0.0021 (7)0.0094 (8)
C80.0433 (7)0.0515 (8)0.0360 (6)0.0045 (6)0.0052 (5)0.0021 (6)
C90.0424 (7)0.0464 (7)0.0362 (6)0.0019 (6)0.0048 (5)0.0007 (5)
C100.0500 (8)0.0642 (9)0.0313 (6)0.0075 (7)0.0032 (6)0.0007 (6)
C110.0488 (8)0.0655 (9)0.0323 (6)0.0058 (7)0.0084 (6)0.0027 (6)
C120.0416 (7)0.0495 (7)0.0373 (6)0.0022 (6)0.0068 (5)0.0035 (5)
C130.0453 (7)0.0559 (8)0.0336 (6)0.0056 (6)0.0073 (5)0.0061 (6)
C140.0469 (7)0.0529 (8)0.0342 (6)0.0037 (6)0.0105 (5)0.0029 (6)
C150.0416 (7)0.0655 (9)0.0392 (7)0.0039 (6)0.0079 (5)0.0044 (6)
C160.0409 (7)0.0684 (10)0.0392 (7)0.0105 (7)0.0081 (5)0.0024 (6)
C170.0696 (11)0.0615 (10)0.0682 (11)0.0009 (9)0.0160 (9)0.0041 (8)
C180.0925 (15)0.0827 (14)0.0661 (11)0.0375 (12)0.0196 (11)0.0189 (11)
C190.0544 (10)0.1231 (19)0.0533 (10)0.0295 (12)0.0049 (8)0.0109 (11)
C200.0435 (9)0.1037 (16)0.0787 (12)0.0032 (10)0.0128 (8)0.0250 (12)
C210.0550 (9)0.0655 (11)0.0679 (10)0.0015 (8)0.0194 (8)0.0010 (9)
N10.0455 (6)0.0575 (7)0.0416 (6)0.0064 (5)0.0157 (5)0.0054 (5)
N20.0444 (6)0.0767 (9)0.0346 (6)0.0120 (6)0.0061 (5)0.0055 (6)
O10.0676 (7)0.1128 (10)0.0439 (6)0.0328 (7)0.0157 (5)0.0044 (6)
O20.0462 (6)0.1212 (11)0.0388 (5)0.0096 (6)0.0040 (4)0.0165 (6)
O30.0488 (6)0.1116 (10)0.0397 (5)0.0235 (6)0.0051 (4)0.0081 (6)
Geometric parameters (Å, º) top
C1—H1A0.96C14—C131.389 (2)
C1—H1B0.96C14—C91.396 (3)
C1—H1C0.96C14—H141.006 (16)
C1—H1D0.96C15—O21.200 (3)
C1—H1E0.96C15—O31.375 (2)
C1—H1F0.96C16—C171.369 (3)
C2—C11.507 (3)C16—C211.373 (3)
C3—C41.397 (3)C17—C181.393 (4)
C4—C51.383 (3)C17—H170.91 (2)
C4—H40.983 (18)C18—H180.90 (3)
C5—C61.376 (3)C19—C201.360 (4)
C5—H50.99 (2)C19—C181.360 (4)
C6—H60.98 (2)C19—H191.03 (2)
C7—C61.392 (3)C20—H201.01 (3)
C7—H71.00 (2)C21—C201.386 (4)
C8—C31.399 (3)C21—H210.94 (2)
C8—C71.400 (3)N1—C21.345 (3)
C9—C101.396 (3)N1—C31.431 (3)
C9—C81.495 (2)N1—H1N0.90 (2)
C10—C111.393 (2)N2—C151.346 (3)
C10—H100.998 (17)N2—C121.420 (2)
C11—H110.971 (17)N2—H2N0.91 (2)
C12—C111.390 (3)O1—C21.225 (2)
C12—C131.397 (3)O3—C161.406 (3)
C13—H130.967 (16)
C2—C1—H1A109.5C14—C13—H13119.4 (9)
C2—C1—H1B109.5C14—C9—C8121.21 (16)
C2—C1—H1C109.5C15—N2—C12125.06 (15)
C2—C1—H1D109.5C15—N2—H2N115.9 (12)
C2—C1—H1E109.5C15—O3—C16115.45 (15)
C2—C1—H1F109.5C16—C17—C18118.5 (2)
C2—N1—C3125.31 (16)C16—C17—H17119.4 (14)
C2—N1—H1N117.5 (13)C16—C21—C20119.4 (2)
C3—C4—H4117.3 (11)C16—C21—H21120.6 (14)
C3—C8—C7117.31 (15)C17—C16—C21120.86 (19)
C3—C8—C9122.41 (15)C17—C16—O3119.22 (16)
C3—N1—H1N116.5 (13)C17—C18—H18119.9 (16)
C4—C3—C8120.66 (16)C18—C17—H17122.0 (14)
C4—C3—N1119.87 (16)C18—C19—H19119.4 (12)
C4—C5—H5121.2 (12)C19—C18—C17120.9 (2)
C5—C4—C3120.56 (18)C19—C18—H18119.2 (16)
C5—C4—H4122.2 (11)C19—C20—C21120.3 (2)
C5—C6—C7119.71 (19)C19—C20—H20117.7 (15)
C5—C6—H6118.5 (12)C20—C19—C18120.0 (2)
C6—C5—C4119.83 (17)C20—C19—H19120.6 (12)
C6—C5—H5119.0 (12)C20—C21—H21120.0 (15)
C6—C7—C8121.87 (18)C21—C16—O3119.91 (17)
C6—C7—H7119.7 (11)C21—C20—H20122.0 (15)
C7—C6—H6121.7 (12)H1A—C1—H1B109.5
C7—C8—C9120.26 (16)H1A—C1—H1C109.5
C8—C3—N1119.40 (14)H1A—C1—H1D141.1
C8—C7—H7118.4 (11)H1A—C1—H1E56.3
C9—C10—H10117.6 (9)H1A—C1—H1F56.3
C9—C14—H14119.5 (9)H1B—C1—H1C109.5
C10—C11—H11119.5 (10)H1B—C1—H1D56.3
C10—C9—C14117.20 (16)H1B—C1—H1E141.1
C10—C9—C8121.54 (16)H1B—C1—H1F56.3
C11—C10—C9121.13 (16)H1C—C1—H1D56.3
C11—C10—H10121.3 (9)H1C—C1—H1E56.3
C11—C12—C13118.66 (16)H1C—C1—H1F141.1
C11—C12—N2118.01 (16)H1D—C1—H1E109.5
C12—C11—C10120.89 (16)H1D—C1—H1F109.5
C12—C11—H11119.5 (10)H1E—C1—H1F109.5
C12—C13—H13120.7 (9)N1—C2—C1115.96 (17)
C12—N2—H2N118.0 (12)N2—C15—O3110.12 (16)
C13—C12—N2123.33 (16)O1—C2—C1122.82 (16)
C13—C14—C9122.24 (16)O1—C2—N1121.22 (17)
C13—C14—H14118.2 (9)O2—C15—N2127.43 (17)
C14—C13—C12119.84 (16)O2—C15—O3122.44 (17)
C2—N1—C3—C458.4 (2)C13—C14—C9—C101.5 (2)
C2—N1—C3—C8124.6 (2)C13—C14—C9—C8178.8 (1)
C3—C4—C5—C61.4 (3)C14—C9—C10—C110.8 (2)
C3—C8—C7—C62.4 (3)C14—C9—C8—C347.6 (2)
C3—N1—C2—C1176.2 (1)C14—C9—C8—C7131.2 (2)
C3—N1—C2—O13.3 (2)C15—N2—C12—C11159.5 (2)
C4—C5—C6—C71.2 (3)C15—N2—C12—C1320.4 (2)
C7—C8—C3—C42.2 (2)C15—O3—C16—C1793.9 (2)
C7—C8—C3—N1174.7 (1)C15—O3—C16—C2187.1 (2)
C8—C3—C4—C50.4 (2)C16—C17—C18—C190.2 (3)
C8—C7—C6—C50.8 (3)C16—C21—C20—C190.3 (3)
C8—C9—C10—C11178.2 (1)C17—C16—C21—C201.6 (2)
C9—C10—C11—C121.2 (2)C18—C19—C20—C211.1 (3)
C9—C14—C13—C120.1 (2)C20—C19—C18—C171.1 (3)
C9—C8—C3—C4176.5 (1)C21—C16—C17—C181.6 (3)
C9—C8—C3—N16.5 (2)N1—C3—C4—C5176.6 (1)
C9—C8—C7—C6176.3 (2)N2—C12—C11—C10177.4 (1)
C10—C9—C8—C3135.2 (2)N2—C12—C13—C14178.0 (1)
C10—C9—C8—C746.1 (2)N2—C15—O3—C16178.2 (1)
C11—C12—C13—C141.9 (2)O2—C15—O3—C160.9 (2)
C12—N2—C15—O24.9 (3)O3—C16—C17—C18179.5 (1)
C12—N2—C15—O3176.1 (1)O3—C16—C21—C20179.5 (1)
C13—C12—C11—C102.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O1i0.91 (2)1.96 (2)2.855 (5)169 (2)
C1—H1D···O3ii0.962.393.328 (6)166
C4—H4···O2iii0.98 (2)2.57 (2)3.434 (6)147 (1)
C10—H10···O2iv0.99 (2)2.35 (2)3.318 (6)164 (1)
C11—H11···O1i0.97 (2)2.65 (2)3.410 (6)136 (1)
Symmetry codes: (i) x+1/2, y+1/2, z1/2; (ii) x1/2, y+1/2, z+1/2; (iii) x+1/2, y+1/2, z+3/2; (iv) x1/2, y+1/2, z1/2.
 

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