[Journal logo]

Volume 69 
Part 1 
Page o76  
January 2013  

Received 21 November 2012
Accepted 22 November 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.092
Data-to-parameter ratio = 15.1
Details
Open access

N-(2,3-Dichlorophenyl)-2-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, C12H8Cl2N2O4S, the N-C bond in the C-SO2-NH-C segment has gauche torsions with respect to the S=O bonds. Further, the N-H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the aniline ring. The molecule is twisted at the S-N bond with a torsion angle of 61.15 (18)°. The dihedral angle between the planes of the benzene rings is 68.00 (6)°. The amide H atom exhibits an intramolecular bifurcated N-H...(O,O) hydrogen bond. In the crystal, pairs of N-H...O(S) hydrogen bonds link the molecules into inversion dimers with R22(8) motifs.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994[Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.]), of N-arylsulfonamides, see: Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o3188.]); Gowda et al. (2002[Gowda, B. T., Jyothi, K. & D'Souza, J. D. (2002). Z. Naturforsch. Teil A, 57, 967-973.]) and of N-chloroaryl-sulfonamides, see: Gowda & Shetty (2004[Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.]); Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8Cl2N2O4S

  • Mr = 347.16

  • Monoclinic, P 21 /n

  • a = 8.2197 (5) Å

  • b = 15.863 (1) Å

  • c = 11.0108 (6) Å

  • [beta] = 93.450 (6)°

  • V = 1433.09 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.61 mm-1

  • T = 293 K

  • 0.44 × 0.36 × 0.28 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 = 0.774, Tmax = 0.847

  • 5760 measured reflections

  • 2923 independent reflections

  • 2304 reflections with I > 2[sigma](I)

  • Rint = 0.013

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.092

  • S = 1.01

  • 2923 reflections

  • 193 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.83 (2) 2.48 (2) 3.136 (2) 137 (2)
N1-H1N...O3 0.83 (2) 2.51 (2) 3.065 (3) 125 (2)
Symmetry code: (i) -x, -y+2, -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: RZ5027 ).


Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the 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, o3188.  [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 (2013). E69, o76  [ doi:10.1107/S1600536812048076 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.