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The title compound, C6H5ClN2O2, exists as a planar mol­ecule; adjacent mol­ecules are linked by N...O hydrogen bonds into ribbons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019707/bt6685sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019707/bt6685Isup2.hkl
Contains datablock I

CCDC reference: 277214

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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
C6H5ClN2O2Z = 2
Mr = 172.57F(000) = 176
Triclinic, P1Dx = 1.617 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.073 (3) ÅCell parameters from 3038 reflections
b = 7.423 (3) Åθ = 3.1–27.5°
c = 7.711 (3) ŵ = 0.48 mm1
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 tube1299 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.505, Tmax = 0.955k = 79
3525 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.122All 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 parametersΔρmax = 0.38 e Å3
5 restraintsΔρmin = 0.21 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.80361 (7)0.31629 (7)0.13860 (5)0.0635 (2)
O10.3118 (2)0.1475 (2)0.8889 (2)0.0615 (4)
O20.0645 (2)0.2492 (2)0.7162 (2)0.0667 (4)
N10.6846 (2)0.1401 (3)0.7783 (2)0.0540 (4)
N20.2476 (2)0.2088 (2)0.7433 (2)0.0441 (3)
C10.5971 (2)0.1984 (2)0.6259 (2)0.0364 (3)
C20.7202 (2)0.2283 (2)0.4758 (2)0.0404 (3)
C30.6407 (2)0.2864 (2)0.3167 (2)0.0412 (3)
C40.4340 (3)0.3203 (3)0.2930 (2)0.0468 (4)
C50.3114 (2)0.2935 (2)0.4360 (2)0.0425 (4)
C60.3882 (2)0.2334 (2)0.6008 (2)0.0362 (3)
H110.622 (3)0.111 (3)0.869 (2)0.067 (6)*
H120.810 (2)0.127 (3)0.785 (3)0.077 (7)*
H20.861 (2)0.204 (3)0.493 (2)0.054 (5)*
H40.379 (3)0.364 (3)0.182 (2)0.064 (5)*
H50.170 (2)0.317 (3)0.427 (3)0.057 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0644 (3)0.0810 (4)0.0433 (3)0.0359 (3)0.0065 (2)0.0008 (2)
O10.0550 (7)0.0859 (9)0.0463 (7)0.0379 (7)0.0092 (5)0.0182 (6)
O20.0370 (6)0.095 (1)0.0745 (9)0.0370 (6)0.0093 (6)0.0079 (7)
N10.0463 (7)0.082 (1)0.0436 (8)0.0376 (7)0.0187 (6)0.0151 (7)
N20.0380 (6)0.0471 (7)0.0499 (7)0.0222 (5)0.0062 (5)0.0027 (5)
C10.0335 (6)0.0382 (7)0.0396 (7)0.0171 (6)0.0102 (5)0.0010 (5)
C20.0330 (7)0.0459 (8)0.0441 (8)0.0190 (6)0.0069 (6)0.0003 (6)
C30.0429 (7)0.0415 (7)0.0375 (7)0.0186 (6)0.0008 (6)0.0021 (6)
C40.0496 (8)0.0507 (8)0.0392 (8)0.0203 (7)0.0161 (6)0.0037 (6)
C50.0355 (7)0.0450 (8)0.0482 (8)0.0171 (6)0.0155 (6)0.0013 (6)
C60.0319 (7)0.0371 (7)0.0419 (8)0.0171 (6)0.0080 (5)0.0005 (6)
Geometric parameters (Å, º) top
Cl1—C31.730 (2)C3—C41.399 (2)
O1—N21.231 (2)C4—C51.362 (2)
O2—N21.229 (2)C5—C61.398 (2)
N1—C11.340 (2)N1—H110.84 (1)
N2—C61.432 (2)N1—H120.85 (1)
C1—C21.411 (2)C2—H20.95 (1)
C1—C61.414 (2)C4—H40.95 (1)
C2—C31.364 (2)C5—H50.94 (1)
O2—N2—O1121.5 (1)C5—C6—C1121.2 (1)
O2—N2—C6118.7 (1)C5—C6—N2117.6 (1)
O1—N2—C6119.8 (1)C1—C6—N2121.2 (1)
N1—C1—C2118.6 (1)C1—N1—H11122 (2)
N1—C1—C6125.5 (1)C1—N1—H12121 (2)
C2—C1—C6116.0 (1)H11—N1—H12117 (2)
C3—C2—C1121.4 (1)C3—C2—H2123 (1)
C2—C3—C4122.3 (1)C1—C2—H2116 (1)
C2—C3—Cl1118.5 (1)C3—C4—H4122 (1)
C4—C3—Cl1119.3 (1)C5—C4—H4121 (1)
C5—C4—C3117.5 (1)C4—C5—H5121 (1)
C4—C5—C6121.6 (1)C6—C5—H5118 (1)
N1—C1—C2—C3179.6 (1)N1—C1—C6—C5179.8 (2)
C6—C1—C2—C30.3 (2)C2—C1—C6—C50.1 (2)
C1—C2—C3—C40.2 (2)N1—C1—C6—N20.3 (2)
C1—C2—C3—Cl1179.1 (1)C2—C1—C6—N2179.8 (1)
C2—C3—C4—C50.1 (2)O2—N2—C6—C52.9 (2)
Cl1—C3—C4—C5179.4 (1)O1—N2—C6—C5176.8 (1)
C3—C4—C5—C60.3 (2)O2—N2—C6—C1177.0 (1)
C4—C5—C6—C10.2 (2)O1—N2—C6—C13.3 (2)
C4—C5—C6—N2179.9 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O10.84 (1)2.07 (2)2.633 (2)124 (2)
N1—H11···O1i0.84 (1)2.45 (2)3.152 (2)141 (2)
N1—H12···O2ii0.85 (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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