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organic compounds
The O=C-C=N sequence of atoms in the title molecule [alternative name: 2,3-diphenyl-4-(4-nitrophenyl)-1-oxa-4-azabutadiene], C20H14N2O3, adopts a gauche conformation, with an O=C-C=N torsion angle of 88.9 (1)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806027383/lh2137sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806027383/lh2137Isup2.hkl |
CCDC reference: 618283
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- R factor = 0.059
- wR factor = 0.160
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C7 - C8 ... 1.53 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
2-(4-Nitrophenylimino)-1,2-diphenylethanone top
Crystal data top
C20H14N2O3 | F(000) = 688 |
Mr = 330.33 | Dx = 1.340 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2559 reflections |
a = 8.8265 (7) Å | θ = 2.5–26.9° |
b = 11.5590 (9) Å | µ = 0.09 mm−1 |
c = 16.365 (1) Å | T = 292 K |
β = 101.323 (1)° | Block, yellow |
V = 1637.1 (2) Å3 | 0.36 × 0.23 × 0.19 mm |
Z = 4 |
Data collection top
Bruker APEX CCD area-detector diffractometer | 2574 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
φ and ω scans | h = −11→10 |
8569 measured reflections | k = −8→14 |
3684 independent reflections | l = −18→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.086P)2] where P = (Fo2 + 2Fc2)/3 |
3684 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.6066 (2) | 0.3791 (1) | 0.23691 (1) | 0.0613 (4) | |
O2 | 0.0896 (2) | 0.2951 (1) | 0.48657 (1) | 0.0768 (5) | |
O3 | −0.0591 (2) | 0.4300 (1) | 0.4244 (1) | 0.0699 (4) | |
N1 | 0.5782 (2) | 0.5997 (1) | 0.3506 (1) | 0.0461 (4) | |
N2 | 0.0686 (2) | 0.3850 (2) | 0.4462 (1) | 0.0562 (4) | |
C1 | 0.7683 (2) | 0.6346 (1) | 0.2674 (1) | 0.0422 (4) | |
C2 | 0.8150 (2) | 0.7382 (2) | 0.3062 (1) | 0.0612 (5) | |
C3 | 0.9394 (3) | 0.7977 (2) | 0.2875 (2) | 0.0734 (7) | |
C4 | 1.0203 (2) | 0.7527 (2) | 0.2303 (1) | 0.0682 (6) | |
C5 | 0.9755 (2) | 0.6500 (2) | 0.1922 (1) | 0.0669 (6) | |
C6 | 0.8494 (2) | 0.5914 (2) | 0.2099 (1) | 0.0545 (5) | |
C7 | 0.6331 (2) | 0.5725 (1) | 0.2866 (1) | 0.0397 (4) | |
C8 | 0.5637 (2) | 0.4785 (1) | 0.2250 (1) | 0.0410 (4) | |
C9 | 0.4487 (2) | 0.5158 (1) | 0.1510 (1) | 0.0403 (4) | |
C10 | 0.3954 (2) | 0.4358 (2) | 0.0885 (1) | 0.0570 (5) | |
C11 | 0.2866 (3) | 0.4679 (2) | 0.0203 (1) | 0.0756 (7) | |
C12 | 0.2309 (3) | 0.5793 (2) | 0.0129 (1) | 0.0717 (6) | |
C13 | 0.2837 (2) | 0.6604 (2) | 0.0736 (1) | 0.0585 (5) | |
C14 | 0.3930 (2) | 0.6285 (2) | 0.1429 (1) | 0.0467 (4) | |
C15 | 0.4495 (2) | 0.5420 (2) | 0.3710 (1) | 0.0429 (4) | |
C16 | 0.4614 (2) | 0.4301 (2) | 0.4020 (1) | 0.0563 (5) | |
C17 | 0.3381 (2) | 0.3791 (2) | 0.4277 (1) | 0.0568 (5) | |
C18 | 0.2023 (2) | 0.4396 (2) | 0.4213 (1) | 0.0470 (4) | |
C19 | 0.1876 (2) | 0.5518 (2) | 0.3916 (1) | 0.0536 (5) | |
C20 | 0.3130 (2) | 0.6036 (2) | 0.3681 (1) | 0.0517 (5) | |
H2 | 0.7621 | 0.7682 | 0.3453 | 0.073* | |
H3 | 0.9689 | 0.8681 | 0.3133 | 0.088* | |
H4 | 1.1047 | 0.7924 | 0.2179 | 0.082* | |
H5 | 1.0301 | 0.6192 | 0.1542 | 0.080* | |
H6 | 0.8187 | 0.5221 | 0.1829 | 0.065* | |
H10 | 0.4335 | 0.3606 | 0.0928 | 0.068* | |
H11 | 0.2504 | 0.4141 | −0.0212 | 0.091* | |
H12 | 0.1570 | 0.6001 | −0.0335 | 0.086* | |
H13 | 0.2464 | 0.7358 | 0.0681 | 0.070* | |
H14 | 0.4292 | 0.6827 | 0.1841 | 0.056* | |
H16 | 0.5532 | 0.3893 | 0.4053 | 0.068* | |
H17 | 0.3465 | 0.3044 | 0.4492 | 0.068* | |
H19 | 0.0948 | 0.5915 | 0.3876 | 0.064* | |
H20 | 0.3063 | 0.6802 | 0.3502 | 0.062* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.070 (1) | 0.041 (1) | 0.071 (1) | 0.009 (1) | 0.009 (1) | 0.001 (1) |
O2 | 0.089 (1) | 0.074 (1) | 0.071 (1) | −0.025 (1) | 0.025 (1) | 0.012 (1) |
O3 | 0.053 (1) | 0.085 (1) | 0.077 (1) | −0.015 (1) | 0.024 (1) | −0.013 (1) |
N1 | 0.040 (1) | 0.052 (1) | 0.047 (1) | −0.003 (1) | 0.010 (1) | −0.002 (1) |
N2 | 0.063 (1) | 0.063 (1) | 0.046 (1) | −0.020 (1) | 0.020 (1) | −0.012 (1) |
C1 | 0.036 (1) | 0.046 (1) | 0.043 (1) | 0.001 (1) | 0.005 (1) | 0.006 (1) |
C2 | 0.059 (1) | 0.059 (1) | 0.068 (1) | −0.013 (1) | 0.017 (1) | −0.009 (1) |
C3 | 0.066 (1) | 0.067 (2) | 0.084 (2) | −0.026 (1) | 0.007 (1) | 0.001 (1) |
C4 | 0.045 (1) | 0.091 (2) | 0.066 (1) | −0.016 (1) | 0.004 (1) | 0.030 (1) |
C5 | 0.050 (1) | 0.092 (2) | 0.062 (1) | −0.004 (1) | 0.019 (1) | 0.014 (1) |
C6 | 0.048 (1) | 0.063 (1) | 0.055 (1) | −0.003 (1) | 0.015 (1) | 0.000 (1) |
C7 | 0.034 (1) | 0.041 (1) | 0.043 (1) | 0.004 (1) | 0.006 (1) | 0.003 (1) |
C8 | 0.037 (1) | 0.037 (1) | 0.052 (1) | 0.000 (1) | 0.016 (1) | 0.000 (1) |
C9 | 0.037 (1) | 0.040 (1) | 0.045 (1) | −0.006 (1) | 0.013 (1) | −0.001 (1) |
C10 | 0.067 (1) | 0.047 (1) | 0.057 (1) | −0.008 (1) | 0.013 (1) | −0.008 (1) |
C11 | 0.092 (2) | 0.071 (2) | 0.056 (1) | −0.017 (1) | −0.004 (1) | −0.013 (1) |
C12 | 0.067 (1) | 0.083 (2) | 0.057 (1) | −0.009 (1) | −0.007 (1) | 0.007 (1) |
C13 | 0.049 (1) | 0.058 (1) | 0.065 (1) | 0.004 (1) | 0.005 (1) | 0.010 (1) |
C14 | 0.042 (1) | 0.047 (1) | 0.051 (1) | −0.001 (1) | 0.008 (1) | −0.003 (1) |
C15 | 0.043 (1) | 0.050 (1) | 0.037 (1) | −0.004 (1) | 0.010 (1) | −0.004 (1) |
C16 | 0.048 (1) | 0.052 (1) | 0.071 (1) | 0.007 (1) | 0.018 (1) | 0.003 (1) |
C17 | 0.063 (1) | 0.046 (1) | 0.064 (1) | −0.003 (1) | 0.017 (1) | 0.005 (1) |
C18 | 0.050 (1) | 0.053 (1) | 0.040 (1) | −0.011 (1) | 0.013 (1) | −0.004 (1) |
C19 | 0.044 (1) | 0.061 (1) | 0.058 (1) | 0.005 (1) | 0.015 (1) | 0.007 (1) |
C20 | 0.048 (1) | 0.050 (1) | 0.059 (1) | 0.002 (1) | 0.015 (1) | 0.011 (1) |
Geometric parameters (Å, º) top
O1—C8 | 1.213 (2) | C15—C16 | 1.385 (3) |
O2—N2 | 1.226 (2) | C15—C20 | 1.393 (2) |
O3—N2 | 1.228 (2) | C16—C17 | 1.375 (3) |
N1—C7 | 1.277 (2) | C17—C18 | 1.373 (3) |
N1—C15 | 1.413 (2) | C18—C19 | 1.382 (3) |
N2—C18 | 1.465 (2) | C19—C20 | 1.378 (3) |
C1—C2 | 1.380 (2) | C2—H2 | 0.93 |
C1—C6 | 1.382 (3) | C3—H3 | 0.93 |
C1—C7 | 1.478 (2) | C4—H4 | 0.93 |
C2—C3 | 1.380 (3) | C5—H5 | 0.93 |
C3—C4 | 1.386 (3) | C6—H6 | 0.93 |
C4—C5 | 1.362 (3) | C10—H10 | 0.93 |
C5—C6 | 1.381 (3) | C11—H11 | 0.93 |
C7—C8 | 1.526 (2) | C12—H12 | 0.93 |
C8—C9 | 1.482 (2) | C13—H13 | 0.93 |
C9—C14 | 1.389 (2) | C14—H14 | 0.93 |
C9—C10 | 1.391 (2) | C16—H16 | 0.93 |
C10—C11 | 1.373 (3) | C17—H17 | 0.93 |
C11—C12 | 1.375 (3) | C19—H19 | 0.93 |
C12—C13 | 1.379 (3) | C20—H20 | 0.93 |
C13—C14 | 1.387 (2) | ||
C7—N1—C15 | 122.0 (2) | C17—C18—N2 | 119.9 (2) |
O2—N2—O3 | 123.2 (2) | C19—C18—N2 | 118.4 (2) |
O2—N2—C18 | 118.0 (2) | C20—C19—C18 | 118.8 (2) |
O3—N2—C18 | 118.7 (2) | C19—C20—C15 | 120.3 (2) |
C2—C1—C6 | 118.6 (2) | C1—C2—H2 | 119.7 |
C2—C1—C7 | 120.3 (2) | C3—C2—H2 | 119.7 |
C6—C1—C7 | 121.1 (2) | C2—C3—H3 | 120.0 |
C1—C2—C3 | 120.6 (2) | C4—C3—H3 | 120.0 |
C2—C3—C4 | 120.1 (2) | C5—C4—H4 | 120.2 |
C5—C4—C3 | 119.6 (2) | C3—C4—H4 | 120.2 |
C4—C5—C6 | 120.4 (2) | C4—C5—H5 | 119.8 |
C5—C6—C1 | 120.8 (2) | C6—C5—H5 | 119.8 |
N1—C7—C1 | 120.4 (2) | C5—C6—H6 | 119.6 |
N1—C7—C8 | 123.4 (1) | C1—C6—H6 | 119.6 |
C1—C7—C8 | 116.2 (1) | C11—C10—H10 | 120.0 |
O1—C8—C9 | 123.3 (2) | C9—C10—H10 | 120.0 |
O1—C8—C7 | 119.7 (2) | C10—C11—H11 | 119.8 |
C9—C8—C7 | 117.0 (1) | C12—C11—H11 | 119.8 |
C14—C9—C10 | 119.3 (2) | C11—C12—H12 | 119.7 |
C14—C9—C8 | 121.6 (2) | C13—C12—H12 | 119.7 |
C10—C9—C8 | 119.1 (2) | C12—C13—H13 | 120.3 |
C11—C10—C9 | 120.0 (2) | C14—C13—H13 | 120.3 |
C10—C11—C12 | 120.4 (2) | C13—C14—H14 | 119.8 |
C11—C12—C13 | 120.6 (2) | C9—C14—H14 | 119.8 |
C12—C13—C14 | 119.4 (2) | C17—C16—H16 | 119.8 |
C13—C14—C9 | 120.3 (2) | C15—C16—H16 | 119.8 |
C16—C15—C20 | 119.5 (2) | C18—C17—H17 | 120.4 |
C16—C15—N1 | 121.4 (2) | C16—C17—H17 | 120.4 |
C20—C15—N1 | 118.8 (2) | C20—C19—H19 | 120.6 |
C17—C16—C15 | 120.4 (2) | C18—C19—H19 | 120.6 |
C18—C17—C16 | 119.3 (2) | C19—C20—H20 | 119.8 |
C17—C18—C19 | 121.7 (2) | C15—C20—H20 | 119.8 |
C6—C1—C2—C3 | 0.4 (3) | C8—C9—C10—C11 | 178.7 (2) |
C7—C1—C2—C3 | −178.8 (2) | C9—C10—C11—C12 | 0.7 (3) |
C1—C2—C3—C4 | −1.0 (3) | C10—C11—C12—C13 | 0.2 (4) |
C2—C3—C4—C5 | 0.5 (3) | C11—C12—C13—C14 | −0.6 (3) |
C3—C4—C5—C6 | 0.6 (3) | C12—C13—C14—C9 | 0.0 (3) |
C4—C5—C6—C1 | −1.2 (3) | C10—C9—C14—C13 | 0.9 (3) |
C2—C1—C6—C5 | 0.7 (3) | C8—C9—C14—C13 | −179.0 (2) |
C7—C1—C6—C5 | 179.9 (2) | C7—N1—C15—C16 | 72.3 (2) |
C15—N1—C7—C1 | −179.8 (2) | C7—N1—C15—C20 | −114.5 (2) |
C15—N1—C7—C8 | 1.8 (2) | C20—C15—C16—C17 | 1.6 (3) |
C2—C1—C7—N1 | −14.8 (2) | N1—C15—C16—C17 | 174.8 (2) |
C6—C1—C7—N1 | 166.0 (2) | C15—C16—C17—C18 | 0.9 (3) |
C2—C1—C7—C8 | 163.7 (2) | C16—C17—C18—C19 | −1.7 (3) |
C6—C1—C7—C8 | −15.5 (2) | C16—C17—C18—N2 | 178.2 (2) |
N1—C7—C8—O1 | −88.9 (2) | O2—N2—C18—C17 | 13.5 (2) |
C1—C7—C8—O1 | 92.6 (2) | O3—N2—C18—C17 | −165.1 (2) |
N1—C7—C8—C9 | 93.0 (2) | O2—N2—C18—C19 | −166.6 (2) |
C1—C7—C8—C9 | −85.5 (2) | O3—N2—C18—C19 | 14.8 (2) |
O1—C8—C9—C14 | 174.7 (2) | C17—C18—C19—C20 | −0.1 (3) |
C7—C8—C9—C14 | −7.3 (2) | N2—C18—C19—C20 | 180.0 (2) |
O1—C8—C9—C10 | −5.3 (2) | C18—C19—C20—C15 | 2.7 (3) |
C7—C8—C9—C10 | 172.7 (2) | C16—C15—C20—C19 | −3.5 (3) |
C14—C9—C10—C11 | −1.3 (3) | N1—C15—C20—C19 | −176.8 (2) |
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