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Volume 68 
Part 12 
Page o3424  
December 2012  

Received 16 November 2012
Accepted 19 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.062
wR = 0.163
Data-to-parameter ratio = 13.2
Details
Open access

N-(3-Chlorophenyl)-4-nitrobenzenesulfonamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

There are two independent molecules in the asymmetric unit of the title compound, C12H9ClN2O4S, in which the dihedral angles between the planes of the benzene rings are 46.90 (14) and 44.50 (14)°. In the crystal, N-H...O hydrogen bonds link the molecules into zigzag chains parallel to the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2576.]); Gowda et al. (2002[Gowda, B. T., Jyothi, K. & D'Souza, J. D. (2002). Z. Naturforsch. Teil A, 57, 967-973.]) and of N-chloroarylamides, see: Gowda & Shetty (2004[Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.]); Gowda & Weiss (1994[Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.]); Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9ClN2O4S

  • Mr = 312.72

  • Monoclinic, P 21 /n

  • a = 14.3419 (8) Å

  • b = 7.7579 (4) Å

  • c = 23.895 (1) Å

  • [beta] = 90.345 (5)°

  • V = 2658.6 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.46 mm-1

  • T = 293 K

  • 0.48 × 0.40 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.810, Tmax = 0.914

  • 9649 measured reflections

  • 4839 independent reflections

  • 3112 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.163

  • S = 1.05

  • 4839 reflections

  • 367 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.83 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O8 0.87 (2) 2.22 (2) 3.052 (4) 163 (3)
N3-H3N...O4i 0.85 (2) 2.36 (2) 3.135 (4) 153 (4)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6857 ).


Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under UGC-BSR one-time grant to faculty and the Department of Science and Technology, Government of India, New Delhi, for the research grant under its promotion of university research and scientific excellence programme.

References

Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2576.  [CSD] [CrossRef] [details]
Gowda, B. T., Jyothi, K. & D'Souza, J. D. (2002). Z. Naturforsch. Teil A, 57, 967-973.  [ChemPort]
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.  [ISI] [CrossRef] [ChemPort]
Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.  [ChemPort]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3424  [ doi:10.1107/S1600536812047496 ]

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