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Volume 68 
Part 12 
Page o3482  
December 2012  

Received 21 November 2012
Accepted 25 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.092
Data-to-parameter ratio = 15.1
Details
Open access

N-(3,5-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 C-S-N-C torsion angle is 49.34 (18)° and the dihedral angle between the benzene rings is 71.92 (10)°. The amide H atom exhibits bifurcated hydrogen bonding. The N-H bond is syn to the ortho-nitro group enabling the formation of an S(7) loop. In the crystal, pairs of N-H...O(S) hydrogen bonds link the molecules into inversion dimers via R22(8) rings.

Related literature

For 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.]); Shahwar et al. (2012[Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.]), of N-arylsulfonamides, see: Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2823.]) and of N-chloroarylsulfonamides, see: 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.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8Cl2N2O4S

  • Mr = 347.16

  • Triclinic, [P \overline 1]

  • a = 8.2823 (8) Å

  • b = 8.3436 (9) Å

  • c = 10.670 (1) Å

  • [alpha] = 76.730 (8)°

  • [beta] = 89.298 (9)°

  • [gamma] = 86.875 (9)°

  • V = 716.59 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.61 mm-1

  • T = 293 K

  • 0.44 × 0.40 × 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

  • 4766 measured reflections

  • 2925 independent reflections

  • 2600 reflections with I > 2[sigma](I)

  • Rint = 0.009

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.04

  • 2925 reflections

  • 194 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.49 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.85 (2) 2.23 (2) 3.052 (2) 162 (2)
N1-H1N...O3 0.85 (2) 2.44 (2) 2.940 (2) 118 (2)
Symmetry code: (i) -x, -y, -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: TK5173 ).


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]
Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2823.  [CSD] [CrossRef] [details]
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.
Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.  [CSD] [CrossRef] [details]
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, o3482  [ doi:10.1107/S1600536812048283 ]

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