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The title mol­ecule, C6H5ClN2O2, crystallizes with two mol­ecules in the asymmetric unit. Both residues are planar with an intra­molecular hydrogen bond between the amino and nitro groups. Two inter­molecular hydrogen bonds connect the crystallographically independent mol­ecules into a dimer. Dimers are linked by N—H...O hydrogen bonding into a one-dimensional ribbon.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051233/kp2069sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051233/kp2069Isup2.hkl
Contains datablock I

CCDC reference: 633904

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.109
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N12 - C12 .. 5.97 su PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O21 .. 3.13 Ang.
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 28.36 From the CIF: _reflns_number_total 2318 Count of symmetry unique reflns 1801 Completeness (_total/calc) 128.71% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 517 Fraction of Friedel pairs measured 0.287 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS in SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL in SHELXTL; molecular graphics: SHELXP in SHELXTL; software used to prepare material for publication: SHELXTL.

4-Chloro-2-nitroaniline top
Crystal data top
C6H5ClN2O2F(000) = 352
Mr = 172.57Dx = 1.584 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 4637 reflections
a = 11.272 (3) Åθ = 2.4–28.4°
b = 3.8023 (11) ŵ = 0.47 mm1
c = 17.016 (5) ÅT = 293 K
β = 97.051 (8)°Needle, yellow
V = 723.8 (4) Å30.31 × 0.14 × 0.08 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2318 independent reflections
Radiation source: fine-focus sealed tube1544 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scansθmax = 28.4°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1510
Tmin = 0.867, Tmax = 0.963k = 55
4637 measured reflectionsl = 1722
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0323P)2]
where P = (Fo2 + 2Fc2)/3
2318 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.19 e Å3
2 restraintsΔρmin = 0.20 e Å3
Special details top

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.77871 (7)0.0465 (2)0.07583 (5)0.0780 (3)
O110.8895 (2)0.6399 (7)0.41681 (14)0.0952 (9)
O120.99466 (18)0.6457 (7)0.32074 (15)0.0909 (8)
N110.6665 (2)0.4093 (7)0.39475 (16)0.0745 (8)
H11A0.71760.51040.42920.089*
H11B0.59640.35890.40640.089*
N120.9024 (2)0.5700 (6)0.34877 (15)0.0622 (8)
C110.6960 (2)0.3307 (7)0.32310 (16)0.0476 (7)
C120.8067 (2)0.3998 (7)0.29757 (16)0.0440 (7)
C130.8326 (2)0.3156 (7)0.22190 (16)0.0468 (7)
H13A0.90750.36530.20700.056*
C140.7467 (2)0.1588 (7)0.16984 (16)0.0485 (7)
C150.6358 (2)0.0876 (7)0.19272 (18)0.0545 (8)
H15A0.57740.01800.15700.065*
C160.6110 (2)0.1692 (7)0.26618 (18)0.0545 (8)
H16A0.53560.11760.27990.065*
Cl20.28218 (7)0.4235 (2)0.77296 (5)0.0778 (3)
O210.3994 (2)0.2223 (7)0.42951 (12)0.0775 (7)
O220.49801 (18)0.4873 (7)0.52748 (14)0.0812 (7)
N210.1799 (2)0.0049 (7)0.43831 (16)0.0714 (9)
H21A0.11180.09920.42250.086*
H21B0.23190.02130.40580.086*
N220.4073 (2)0.3262 (6)0.49834 (13)0.0532 (6)
C210.2052 (2)0.1021 (7)0.51405 (17)0.0501 (8)
C220.3143 (2)0.2599 (7)0.54579 (15)0.0412 (6)
C230.3364 (2)0.3607 (7)0.62493 (15)0.0445 (7)
H23A0.40830.46890.64370.053*
C240.2534 (2)0.3016 (7)0.67472 (16)0.0488 (7)
C250.1437 (2)0.1526 (8)0.64431 (19)0.0602 (9)
H25A0.08550.11650.67770.072*
C260.1208 (3)0.0592 (8)0.5665 (2)0.0606 (9)
H26A0.04660.03590.54790.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1140 (6)0.0718 (5)0.0484 (4)0.0075 (5)0.0112 (4)0.0080 (4)
O110.0963 (16)0.125 (2)0.0597 (15)0.0148 (15)0.0084 (12)0.0313 (14)
O120.0593 (13)0.123 (2)0.0873 (17)0.0315 (13)0.0023 (12)0.0162 (15)
N110.0780 (16)0.0851 (19)0.0658 (17)0.0016 (14)0.0302 (12)0.0008 (15)
N120.0562 (14)0.0657 (16)0.0616 (17)0.0009 (12)0.0051 (13)0.0097 (13)
C110.0529 (15)0.0437 (15)0.0484 (15)0.0018 (12)0.0154 (12)0.0117 (12)
C120.0409 (13)0.0429 (14)0.0449 (15)0.0012 (11)0.0077 (11)0.0019 (12)
C130.0377 (13)0.0471 (15)0.0558 (17)0.0021 (12)0.0068 (11)0.0060 (13)
C140.0635 (16)0.0391 (14)0.0417 (14)0.0062 (13)0.0018 (12)0.0037 (12)
C150.0449 (16)0.0515 (16)0.0630 (19)0.0025 (13)0.0097 (13)0.0025 (14)
C160.0382 (14)0.0481 (16)0.077 (2)0.0020 (12)0.0064 (13)0.0111 (15)
Cl20.1140 (6)0.0747 (5)0.0485 (4)0.0096 (5)0.0259 (4)0.0080 (4)
O210.0803 (14)0.1087 (17)0.0453 (12)0.0057 (14)0.0143 (10)0.0053 (13)
O220.0606 (12)0.1194 (18)0.0656 (14)0.0306 (12)0.0154 (10)0.0106 (13)
N210.0754 (17)0.0821 (19)0.0516 (16)0.0119 (15)0.0127 (13)0.0101 (14)
N220.0594 (14)0.0601 (14)0.0400 (13)0.0001 (12)0.0058 (11)0.0029 (12)
C210.0466 (15)0.0452 (15)0.0539 (17)0.0063 (12)0.0123 (12)0.0017 (13)
C220.0443 (13)0.0374 (13)0.0413 (13)0.0045 (11)0.0023 (10)0.0048 (11)
C230.0491 (14)0.0394 (14)0.0432 (15)0.0026 (12)0.0007 (11)0.0013 (12)
C240.0571 (16)0.0432 (14)0.0473 (15)0.0027 (13)0.0115 (12)0.0014 (13)
C250.0532 (17)0.0586 (19)0.074 (2)0.0006 (14)0.0264 (14)0.0010 (16)
C260.0434 (16)0.0536 (17)0.082 (2)0.0059 (13)0.0018 (15)0.0006 (16)
Geometric parameters (Å, º) top
Cl1—C141.736 (3)Cl2—C241.727 (3)
O11—N121.214 (3)O21—N221.229 (3)
O12—N121.231 (3)O22—N221.242 (3)
N11—C111.336 (4)N21—C211.348 (4)
N11—H11A0.8600N21—H21A0.8600
N11—H11B0.8600N21—H21B0.8600
N12—C121.452 (3)N22—C221.422 (4)
C11—C121.396 (4)C21—C261.392 (4)
C11—C161.416 (4)C21—C221.414 (4)
C12—C131.392 (4)C22—C231.393 (4)
C13—C141.367 (4)C23—C241.356 (4)
C13—H13A0.9300C23—H23A0.9300
C14—C151.380 (4)C24—C251.400 (4)
C15—C161.350 (4)C25—C261.365 (5)
C15—H15A0.9300C25—H25A0.9300
C16—H16A0.9300C26—H26A0.9300
C11—N11—H11A120.0C21—N21—H21A120.0
C11—N11—H11B120.0C21—N21—H21B120.0
H11A—N11—H11B120.0H21A—N21—H21B120.0
O11—N12—O12121.6 (2)O21—N22—O22120.0 (2)
O11—N12—C12120.2 (3)O21—N22—C22120.8 (2)
O12—N12—C12118.2 (3)O22—N22—C22119.3 (2)
N11—C11—C12125.0 (3)N21—C21—C26119.8 (3)
N11—C11—C16119.8 (3)N21—C21—C22124.4 (3)
C12—C11—C16115.1 (3)C26—C21—C22115.8 (3)
C13—C12—C11122.8 (2)C23—C22—C21122.0 (3)
C13—C12—N12115.7 (2)C23—C22—N22116.3 (2)
C11—C12—N12121.6 (2)C21—C22—N22121.7 (2)
C14—C13—C12119.2 (2)C24—C23—C22120.2 (2)
C14—C13—H13A120.4C24—C23—H23A119.9
C12—C13—H13A120.4C22—C23—H23A119.9
C13—C14—C15119.8 (3)C23—C24—C25118.8 (3)
C13—C14—Cl1119.6 (2)C23—C24—Cl2119.9 (2)
C15—C14—Cl1120.6 (2)C25—C24—Cl2121.3 (2)
C16—C15—C14120.9 (2)C26—C25—C24121.2 (3)
C16—C15—H15A119.5C26—C25—H25A119.4
C14—C15—H15A119.5C24—C25—H25A119.4
C15—C16—C11122.2 (3)C25—C26—C21121.9 (3)
C15—C16—H16A118.9C25—C26—H26A119.0
C11—C16—H16A118.9C21—C26—H26A119.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···O110.862.042.645 (4)127
N21—H21B···O210.862.032.642 (3)127
N11—H11B···O210.862.363.218 (4)176
N11—H11B···O220.862.503.138 (4)131
N21—H21A···O12i0.862.263.017 (3)146
Symmetry code: (i) x1, y1, z.
 

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