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Volume 68 
Part 1 
Page o244  
January 2012  

Received 19 December 2011
Accepted 20 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.058
wR = 0.105
Data-to-parameter ratio = 14.1
Details
Open access

N-(3-Chlorobenzoyl)-3-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, C13H9ClN2O5S, the dihedral angle between the two benzene rings is 83.5 (1)°. In the crystal, molecules are linked via N-H...O(S) hydrogen bonds into helical chains running along the b axis.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003[Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.]); Gowda et al. (2004[Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 59, 845-852.]), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004[Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.]), onN-(aryl)-arylsulfonamides, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Kozisek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656-660.]), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2011[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o3515.]) and on N-chloroarylamides, see: Gowda & Mahadevappa (1983[Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359-362.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9ClN2O5S

  • Mr = 340.73

  • Monoclinic, P 21 /c

  • a = 11.891 (2) Å

  • b = 5.0577 (6) Å

  • c = 23.488 (3) Å

  • [beta] = 90.43 (1)°

  • V = 1412.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.44 mm-1

  • T = 293 K

  • 0.46 × 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 = 0.822, Tmax = 0.957

  • 4873 measured reflections

  • 2840 independent reflections

  • 2204 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.105

  • S = 1.20

  • 2840 reflections

  • 202 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.82 (2) 2.29 (2) 3.100 (3) 169 (3)
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: BT5758 ).


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.

References

Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.  [CSD] [CrossRef] [details]
Gowda, B. T., Jyothi, K., Kozisek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656-660.  [ChemPort]
Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359-362.  [CrossRef] [PubMed] [ChemPort] [ISI]
Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 59, 845-852.  [ChemPort]
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.  [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]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o3515.  [CrossRef] [details]


Acta Cryst (2012). E68, o244  [ doi:10.1107/S1600536811054857 ]

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