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N-(4-Bromobenzylidene)-3-nitroaniline, C13H9BrN2O2, is a non-planar molecule whose two aromatic rings are twisted about the C=N double bond in order to relieve strain [dihedral angle = 17.8 (2)°].
Supporting information
CCDC reference: 621548
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.007 Å
- R factor = 0.059
- wR factor = 0.145
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.108
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 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
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.
N-(4-Bromobenzylidene)-3-nitroaniline
top
Crystal data top
C13H9BrN2O2 | F(000) = 608 |
Mr = 305.13 | Dx = 1.716 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1625 reflections |
a = 13.501 (2) Å | θ = 3.0–24.2° |
b = 3.9390 (5) Å | µ = 3.47 mm−1 |
c = 22.433 (3) Å | T = 292 K |
β = 98.016 (2)° | Needle, light yellow |
V = 1181.3 (3) Å3 | 0.30 × 0.10 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 2648 independent reflections |
Radiation source: fine-focus sealed tube | 1545 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.108 |
φ and ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.422, Tmax = 0.819 | k = −4→5 |
7663 measured reflections | l = −28→25 |
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) = 0.145 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0665P)2] where P = (Fo2 + 2Fc2)/3 |
2648 reflections | (Δ/σ)max = 0.001 |
163 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.53214 (4) | 0.5641 (2) | 0.72734 (3) | 0.0532 (2) | |
O1 | 1.0574 (3) | −0.326 (1) | 0.4470 (2) | 0.067 (1) | |
O2 | 1.0440 (3) | −0.591 (1) | 0.3626 (2) | 0.078 (1) | |
N1 | 0.7053 (3) | 0.051 (1) | 0.4661 (2) | 0.042 (1) | |
N2 | 1.0093 (3) | −0.417 (1) | 0.3997 (2) | 0.048 (1) | |
C1 | 0.6836 (3) | 0.127 (1) | 0.5697 (2) | 0.035 (1) | |
C2 | 0.7300 (4) | 0.100 (1) | 0.6290 (2) | 0.042 (1) | |
C3 | 0.6844 (4) | 0.229 (1) | 0.6754 (2) | 0.043 (1) | |
C4 | 0.5930 (4) | 0.384 (1) | 0.6628 (2) | 0.036 (1) | |
C5 | 0.5459 (4) | 0.418 (1) | 0.6046 (2) | 0.040 (1) | |
C6 | 0.5921 (4) | 0.287 (1) | 0.5586 (2) | 0.040 (1) | |
C7 | 0.7321 (3) | −0.018 (1) | 0.5210 (2) | 0.038 (1) | |
C8 | 0.7573 (4) | −0.101 (1) | 0.4226 (2) | 0.037 (1) | |
C9 | 0.7050 (4) | −0.160 (1) | 0.3665 (2) | 0.041 (1) | |
C10 | 0.7519 (4) | −0.315 (1) | 0.3216 (2) | 0.044 (1) | |
C11 | 0.8506 (4) | −0.401 (1) | 0.3320 (2) | 0.044 (1) | |
C12 | 0.9036 (3) | −0.325 (1) | 0.3877 (2) | 0.037 (1) | |
C13 | 0.8597 (3) | −0.175 (1) | 0.4333 (2) | 0.036 (1) | |
H2 | 0.7919 | −0.0060 | 0.6374 | 0.051* | |
H3 | 0.7154 | 0.2107 | 0.7149 | 0.052* | |
H5 | 0.4842 | 0.5257 | 0.5965 | 0.048* | |
H6 | 0.5609 | 0.3082 | 0.5191 | 0.048* | |
H7 | 0.7851 | −0.1679 | 0.5310 | 0.046* | |
H9 | 0.6380 | −0.0971 | 0.3583 | 0.049* | |
H10 | 0.7151 | −0.3591 | 0.2842 | 0.053* | |
H11 | 0.8814 | −0.5072 | 0.3024 | 0.052* | |
H13 | 0.8974 | −0.1242 | 0.4701 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0625 (4) | 0.0486 (4) | 0.0536 (4) | 0.0026 (3) | 0.0264 (3) | −0.0058 (3) |
O1 | 0.041 (2) | 0.100 (4) | 0.060 (3) | 0.007 (2) | 0.007 (2) | −0.015 (3) |
O2 | 0.053 (3) | 0.106 (4) | 0.078 (3) | 0.018 (3) | 0.018 (2) | −0.033 (3) |
N1 | 0.037 (2) | 0.046 (3) | 0.043 (3) | 0.004 (2) | 0.0114 (19) | −0.005 (2) |
N2 | 0.043 (2) | 0.054 (3) | 0.049 (3) | 0.005 (2) | 0.014 (2) | −0.005 (3) |
C1 | 0.036 (3) | 0.029 (3) | 0.041 (3) | 0.000 (2) | 0.013 (2) | 0.005 (2) |
C2 | 0.036 (3) | 0.042 (3) | 0.050 (3) | 0.008 (2) | 0.010 (2) | 0.006 (3) |
C3 | 0.046 (3) | 0.041 (3) | 0.043 (3) | −0.002 (3) | 0.003 (2) | −0.002 (3) |
C4 | 0.040 (3) | 0.028 (3) | 0.042 (3) | −0.001 (2) | 0.014 (2) | −0.001 (2) |
C5 | 0.034 (3) | 0.036 (3) | 0.053 (3) | 0.010 (2) | 0.015 (2) | 0.005 (3) |
C6 | 0.038 (3) | 0.044 (3) | 0.039 (3) | 0.005 (2) | 0.010 (2) | 0.003 (2) |
C7 | 0.031 (2) | 0.028 (3) | 0.058 (3) | 0.001 (2) | 0.012 (2) | 0.000 (2) |
C8 | 0.036 (3) | 0.031 (3) | 0.046 (3) | −0.001 (2) | 0.013 (2) | 0.005 (2) |
C9 | 0.032 (3) | 0.043 (3) | 0.049 (3) | 0.004 (2) | 0.008 (2) | 0.009 (3) |
C10 | 0.042 (3) | 0.050 (3) | 0.039 (3) | −0.005 (2) | 0.000 (2) | 0.000 (2) |
C11 | 0.053 (3) | 0.039 (3) | 0.041 (3) | −0.005 (3) | 0.013 (2) | −0.001 (3) |
C12 | 0.036 (3) | 0.033 (3) | 0.044 (3) | −0.001 (2) | 0.014 (2) | 0.000 (2) |
C13 | 0.036 (3) | 0.037 (3) | 0.036 (3) | 0.004 (2) | 0.008 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
Br1—C4 | 1.899 (5) | C8—C13 | 1.400 (7) |
O1—N2 | 1.218 (6) | C9—C10 | 1.402 (7) |
O2—N2 | 1.220 (6) | C10—C11 | 1.363 (7) |
N1—C7 | 1.264 (6) | C11—C12 | 1.384 (7) |
N1—C8 | 1.413 (6) | C12—C13 | 1.384 (6) |
N2—C12 | 1.461 (6) | C2—H2 | 0.93 |
C1—C6 | 1.379 (6) | C3—H3 | 0.93 |
C1—C2 | 1.394 (7) | C5—H5 | 0.93 |
C1—C7 | 1.465 (7) | C6—H6 | 0.93 |
C2—C3 | 1.377 (7) | C7—H7 | 0.93 |
C3—C4 | 1.370 (7) | C9—H9 | 0.93 |
C4—C5 | 1.378 (7) | C10—H10 | 0.93 |
C5—C6 | 1.377 (7) | C11—H11 | 0.93 |
C8—C9 | 1.374 (7) | C13—H13 | 0.93 |
| | | |
C7—N1—C8 | 118.6 (4) | C13—C12—N2 | 118.6 (4) |
O1—N2—O2 | 123.4 (5) | C11—C12—N2 | 118.8 (4) |
O1—N2—C12 | 118.4 (4) | C12—C13—C8 | 118.5 (5) |
O2—N2—C12 | 118.1 (5) | C3—C2—H2 | 119.9 |
C6—C1—C2 | 118.6 (4) | C1—C2—H2 | 119.9 |
C6—C1—C7 | 121.7 (5) | C4—C3—H3 | 120.2 |
C2—C1—C7 | 119.6 (4) | C2—C3—H3 | 120.2 |
C3—C2—C1 | 120.3 (5) | C6—C5—H5 | 120.8 |
C4—C3—C2 | 119.6 (5) | C4—C5—H5 | 120.8 |
C3—C4—C5 | 121.4 (5) | C5—C6—H6 | 119.2 |
C3—C4—Br1 | 118.9 (4) | C1—C6—H6 | 119.2 |
C5—C4—Br1 | 119.7 (4) | N1—C7—H7 | 118.5 |
C6—C5—C4 | 118.5 (5) | C1—C7—H7 | 118.5 |
C5—C6—C1 | 121.6 (5) | C8—C9—H9 | 119.8 |
N1—C7—C1 | 123.0 (4) | C10—C9—H9 | 119.8 |
C9—C8—C13 | 119.4 (5) | C11—C10—H10 | 119.5 |
C9—C8—N1 | 117.5 (4) | C9—C10—H10 | 119.5 |
C13—C8—N1 | 122.9 (5) | C10—C11—H11 | 121.0 |
C8—C9—C10 | 120.3 (5) | C12—C11—H11 | 121.0 |
C11—C10—C9 | 121.0 (5) | C12—C13—H13 | 120.8 |
C10—C11—C12 | 118.0 (5) | C8—C13—H13 | 120.8 |
C13—C12—C11 | 122.6 (5) | | |
| | | |
C6—C1—C2—C3 | 0.6 (8) | C13—C8—C9—C10 | 4.4 (8) |
C7—C1—C2—C3 | −178.8 (5) | N1—C8—C9—C10 | −179.1 (5) |
C1—C2—C3—C4 | 0.1 (8) | C8—C9—C10—C11 | −1.8 (8) |
C2—C3—C4—C5 | −0.7 (8) | C9—C10—C11—C12 | −1.2 (8) |
C2—C3—C4—Br1 | −179.4 (4) | C10—C11—C12—C13 | 1.7 (8) |
C3—C4—C5—C6 | 0.8 (8) | C10—C11—C12—N2 | 179.7 (5) |
Br1—C4—C5—C6 | 179.4 (4) | O1—N2—C12—C13 | −7.6 (7) |
C4—C5—C6—C1 | −0.1 (8) | O2—N2—C12—C13 | 169.9 (5) |
C2—C1—C6—C5 | −0.5 (8) | O1—N2—C12—C11 | 174.4 (5) |
C7—C1—C6—C5 | 178.8 (5) | O2—N2—C12—C11 | −8.2 (8) |
C8—N1—C7—C1 | 179.8 (4) | C11—C12—C13—C8 | 0.8 (8) |
C6—C1—C7—N1 | 14.8 (8) | N2—C12—C13—C8 | −177.2 (4) |
C2—C1—C7—N1 | −165.9 (5) | C9—C8—C13—C12 | −3.9 (7) |
C7—N1—C8—C9 | 150.1 (5) | N1—C8—C13—C12 | 179.9 (5) |
C7—N1—C8—C13 | −33.6 (7) | | |
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