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The title compound, C
6H
5ClN
2O
2, exists as a planar molecule; adjacent molecules are linked by N
O hydrogen bonds into ribbons.
Supporting information
CCDC reference: 277214
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.122
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.505 0.955
Tmin' and Tmax expected: 0.855 0.995
RR' = 0.616
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.61
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.04
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - N2 .. 5.05 su
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
2 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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.
5-Chloro-2-nitroaniline
top
Crystal data top
C6H5ClN2O2 | Z = 2 |
Mr = 172.57 | F(000) = 176 |
Triclinic, P1 | Dx = 1.617 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.073 (3) Å | Cell parameters from 3038 reflections |
b = 7.423 (3) Å | θ = 3.1–27.5° |
c = 7.711 (3) Å | µ = 0.48 mm−1 |
α = 83.87 (3)° | T = 295 K |
β = 81.98 (3)° | Plate, yellow |
γ = 62.24 (3)° | 0.32 × 0.21 × 0.01 mm |
V = 354.4 (3) Å3 | |
Data collection top
Rigaki RAXIS-RAPID IP diffractometer | 1608 independent reflections |
Radiation source: fine-focus sealed tube | 1299 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→9 |
Tmin = 0.505, Tmax = 0.955 | k = −7→9 |
3525 measured reflections | l = −9→9 |
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)] = 0.041 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.122 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0843P)2] where P = (Fo2 + 2Fc2)/3 |
1608 reflections | (Δ/σ)max = 0.001 |
120 parameters | Δρmax = 0.38 e Å−3 |
5 restraints | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.80361 (7) | 0.31629 (7) | 0.13860 (5) | 0.0635 (2) | |
O1 | 0.3118 (2) | 0.1475 (2) | 0.8889 (2) | 0.0615 (4) | |
O2 | 0.0645 (2) | 0.2492 (2) | 0.7162 (2) | 0.0667 (4) | |
N1 | 0.6846 (2) | 0.1401 (3) | 0.7783 (2) | 0.0540 (4) | |
N2 | 0.2476 (2) | 0.2088 (2) | 0.7433 (2) | 0.0441 (3) | |
C1 | 0.5971 (2) | 0.1984 (2) | 0.6259 (2) | 0.0364 (3) | |
C2 | 0.7202 (2) | 0.2283 (2) | 0.4758 (2) | 0.0404 (3) | |
C3 | 0.6407 (2) | 0.2864 (2) | 0.3167 (2) | 0.0412 (3) | |
C4 | 0.4340 (3) | 0.3203 (3) | 0.2930 (2) | 0.0468 (4) | |
C5 | 0.3114 (2) | 0.2935 (2) | 0.4360 (2) | 0.0425 (4) | |
C6 | 0.3882 (2) | 0.2334 (2) | 0.6008 (2) | 0.0362 (3) | |
H11 | 0.622 (3) | 0.111 (3) | 0.869 (2) | 0.067 (6)* | |
H12 | 0.810 (2) | 0.127 (3) | 0.785 (3) | 0.077 (7)* | |
H2 | 0.861 (2) | 0.204 (3) | 0.493 (2) | 0.054 (5)* | |
H4 | 0.379 (3) | 0.364 (3) | 0.182 (2) | 0.064 (5)* | |
H5 | 0.170 (2) | 0.317 (3) | 0.427 (3) | 0.057 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0644 (3) | 0.0810 (4) | 0.0433 (3) | −0.0359 (3) | 0.0065 (2) | 0.0008 (2) |
O1 | 0.0550 (7) | 0.0859 (9) | 0.0463 (7) | −0.0379 (7) | −0.0092 (5) | 0.0182 (6) |
O2 | 0.0370 (6) | 0.095 (1) | 0.0745 (9) | −0.0370 (6) | −0.0093 (6) | 0.0079 (7) |
N1 | 0.0463 (7) | 0.082 (1) | 0.0436 (8) | −0.0376 (7) | −0.0187 (6) | 0.0151 (7) |
N2 | 0.0380 (6) | 0.0471 (7) | 0.0499 (7) | −0.0222 (5) | −0.0062 (5) | 0.0027 (5) |
C1 | 0.0335 (6) | 0.0382 (7) | 0.0396 (7) | −0.0171 (6) | −0.0102 (5) | 0.0010 (5) |
C2 | 0.0330 (7) | 0.0459 (8) | 0.0441 (8) | −0.0190 (6) | −0.0069 (6) | −0.0003 (6) |
C3 | 0.0429 (7) | 0.0415 (7) | 0.0375 (7) | −0.0186 (6) | −0.0008 (6) | −0.0021 (6) |
C4 | 0.0496 (8) | 0.0507 (8) | 0.0392 (8) | −0.0203 (7) | −0.0161 (6) | 0.0037 (6) |
C5 | 0.0355 (7) | 0.0450 (8) | 0.0482 (8) | −0.0171 (6) | −0.0155 (6) | 0.0013 (6) |
C6 | 0.0319 (7) | 0.0371 (7) | 0.0419 (8) | −0.0171 (6) | −0.0080 (5) | 0.0005 (6) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.730 (2) | C3—C4 | 1.399 (2) |
O1—N2 | 1.231 (2) | C4—C5 | 1.362 (2) |
O2—N2 | 1.229 (2) | C5—C6 | 1.398 (2) |
N1—C1 | 1.340 (2) | N1—H11 | 0.84 (1) |
N2—C6 | 1.432 (2) | N1—H12 | 0.85 (1) |
C1—C2 | 1.411 (2) | C2—H2 | 0.95 (1) |
C1—C6 | 1.414 (2) | C4—H4 | 0.95 (1) |
C2—C3 | 1.364 (2) | C5—H5 | 0.94 (1) |
| | | |
O2—N2—O1 | 121.5 (1) | C5—C6—C1 | 121.2 (1) |
O2—N2—C6 | 118.7 (1) | C5—C6—N2 | 117.6 (1) |
O1—N2—C6 | 119.8 (1) | C1—C6—N2 | 121.2 (1) |
N1—C1—C2 | 118.6 (1) | C1—N1—H11 | 122 (2) |
N1—C1—C6 | 125.5 (1) | C1—N1—H12 | 121 (2) |
C2—C1—C6 | 116.0 (1) | H11—N1—H12 | 117 (2) |
C3—C2—C1 | 121.4 (1) | C3—C2—H2 | 123 (1) |
C2—C3—C4 | 122.3 (1) | C1—C2—H2 | 116 (1) |
C2—C3—Cl1 | 118.5 (1) | C3—C4—H4 | 122 (1) |
C4—C3—Cl1 | 119.3 (1) | C5—C4—H4 | 121 (1) |
C5—C4—C3 | 117.5 (1) | C4—C5—H5 | 121 (1) |
C4—C5—C6 | 121.6 (1) | C6—C5—H5 | 118 (1) |
| | | |
N1—C1—C2—C3 | 179.6 (1) | N1—C1—C6—C5 | −179.8 (2) |
C6—C1—C2—C3 | −0.3 (2) | C2—C1—C6—C5 | 0.1 (2) |
C1—C2—C3—C4 | 0.2 (2) | N1—C1—C6—N2 | 0.3 (2) |
C1—C2—C3—Cl1 | −179.1 (1) | C2—C1—C6—N2 | −179.8 (1) |
C2—C3—C4—C5 | 0.1 (2) | O2—N2—C6—C5 | −2.9 (2) |
Cl1—C3—C4—C5 | 179.4 (1) | O1—N2—C6—C5 | 176.8 (1) |
C3—C4—C5—C6 | −0.3 (2) | O2—N2—C6—C1 | 177.0 (1) |
C4—C5—C6—C1 | 0.2 (2) | O1—N2—C6—C1 | −3.3 (2) |
C4—C5—C6—N2 | −179.9 (1) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1 | 0.84 (1) | 2.07 (2) | 2.633 (2) | 124 (2) |
N1—H11···O1i | 0.84 (1) | 2.45 (2) | 3.152 (2) | 141 (2) |
N1—H12···O2ii | 0.85 (1) | 2.35 (1) | 3.113 (2) | 150 (2) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x+1, y, z. |
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