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Volume 68 
Part 12 
Page o3497  
December 2012  

Received 16 November 2012
Accepted 27 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.053
wR = 0.110
Data-to-parameter ratio = 14.9
Details
Open access

N-(2-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

In the title compound, C12H9ClN2O4S, the dihedral angle between the benzene rings is 70.60 (11)°. An intramolecular N-H...Cl contact occurs. In the crystal, molecules form inversion dimers via pairs of N-H...O hydrogen bonds.

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, o2766.]); Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]) 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.]). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001[Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.]); Allen et al. (1998[Allen, F. H., Raithby, P. R., Shields, G. P. & Taylor, R. (1998). Chem. Commun. pp. 1043-1044.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9ClN2O4S

  • Mr = 312.72

  • Monoclinic, P 21 /n

  • a = 9.2762 (9) Å

  • b = 12.981 (1) Å

  • c = 11.970 (1) Å

  • [beta] = 110.97 (1)°

  • V = 1345.9 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.45 mm-1

  • T = 293 K

  • 0.42 × 0.20 × 0.10 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 = 0.833, Tmax = 0.956

  • 5256 measured reflections

  • 2748 independent reflections

  • 2019 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.110

  • S = 1.16

  • 2748 reflections

  • 185 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.84 (2) 2.20 (2) 3.003 (3) 159 (3)
N1-H1N...Cl1 0.84 (2) 2.56 (3) 2.984 (3) 112 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

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: BT6858 ).


Acknowledgements

UC thanks Mangalore University for the award of a research fellowship. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.  [ISI] [CrossRef] [PubMed] [ChemPort]
Allen, F. H., Raithby, P. R., Shields, G. P. & Taylor, R. (1998). Chem. Commun. pp. 1043-1044.  [CrossRef]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2766.  [CrossRef] [details]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.  [ISI] [CrossRef] [ChemPort]
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.  [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, o3497  [ doi:10.1107/S1600536812048684 ]

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