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Volume 67 
Part 6 
Page o1401  
June 2011  

Received 4 May 2011
Accepted 6 May 2011
Online 14 May 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.036
wR = 0.079
Data-to-parameter ratio = 15.6
Details
Open access

4-Chloro-N-(2,6-dimethylphenyl)benzenesulfonamide

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, C14H14ClNO2S, the amido H atom orients itself away from both the ortho-methyl groups in the adjacent aromatic ring. The molecule is twisted at the S atom with an C-SO2-NH-C torsion angle of -69.9 (2)°. The two aromatic rings are tilted relative to each other by 31.9 (1)°. In the crystal, the molecules are packed into zigzag chains along the b axis via intermolecular N-H...O hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001[Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.]). For our study of the effect of substituents on the structures of N-(aryl)methanesulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.]), on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1691.]); Shakuntala et al. (2011[Shakuntala, K., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o1252.]) and on the oxidative strengths of N-chloro,N-arylsulfonamides, see: Gowda & Kumar (2003[Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. 26, 403-425.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14ClNO2S

  • Mr = 295.77

  • Orthorhombic, P 21 21 21

  • a = 7.3816 (4) Å

  • b = 10.2916 (7) Å

  • c = 18.312 (1) Å

  • V = 1391.13 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 293 K

  • 0.40 × 0.28 × 0.24 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 = 0.850, Tmax = 0.906

  • 5356 measured reflections

  • 2767 independent reflections

  • 2255 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.079

  • S = 1.02

  • 2767 reflections

  • 177 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1113 Friedel pairs

  • Flack parameter: 0.43 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.82 (2) 2.28 (2) 3.083 (3) 166 (3)
Symmetry code: (i) [-x+2, 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 RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: BQ2299 ).


Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.  [ISI] [CrossRef] [PubMed] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1691.  [CSD] [CrossRef] [details]
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.  [CSD] [CrossRef] [details]
Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. 26, 403-425.  [ChemPort]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Shakuntala, K., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o1252.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2011). E67, o1401  [ doi:10.1107/S160053681101717X ]

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