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

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S160053681101717X

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 (C-C) = 0.004 Å
R = 0.036
wR = 0.079
Data-to-parameter ratio = 15.6
Details

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

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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-HO hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001). For our study of the effect of substituents on the structures of N-(aryl)methanesulfonamides, see: Gowda et al. (2007), on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008); Shakuntala et al. (2011) and on the oxidative strengths of N-chloro,N-arylsulfonamides, see: Gowda & Kumar (2003).

Experimental

Crystal data

C₁₄H₁₄ClNO₂S
M_r = 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 radiation
= 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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.850, T_max = 0.906
5356 measured reflections
2767 independent reflections
2255 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(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
_max = 0.19 e Å^-3
_min = -0.25 e Å^-3
Absolute structure: Flack (1983), 1113 Friedel pairs
Flack parameter: 0.43 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1691.
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.
Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. 26, 403-425.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds