4-Chloro-N-(3-methyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536811019416

Volume 67
Part 6
Page o1540
June 2011

Received 16 May 2011
Accepted 23 May 2011
Online 28 May 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.119
Data-to-parameter ratio = 16.6
Details

4-Chloro-N-(3-methylphenyl)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 crystal of the title compound, C₁₃H₁₂ClNO₂S, the N-H bond is anti to the meta-methyl group in the aniline ring. The C-SO₂-NH-C torsion angle is -57.6 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of 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)-amides, see: Gowda et al. (2004), on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2010); Nirmala et al. (2009); Shakuntala et al. (2011) and on the structures of N-(aryl)methanesulfonamides, see: Gowda et al. (2007).

Experimental

Crystal data

C₁₃H₁₂ClNO₂S
M_r = 281.75
Monoclinic, C 2/c
a = 14.202 (1) Å
b = 14.561 (1) Å
c = 13.271 (1) Å
= 97.292 (9)°
V = 2722.2 (3) Å³
Z = 8
Mo K radiation
= 0.43 mm^-1
T = 293 K
0.48 × 0.44 × 0.40 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 = 0.821, T_max = 0.848
5706 measured reflections
2777 independent reflections
2186 reflections with I > 2(I)
R_int = 0.012

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.119
S = 1.05
2777 reflections
167 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.84 (2)	2.11 (2)	2.942 (2)	172 (2)
Symmetry code: (i) -x+1, -y, -z.

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: DS2114 ).

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.
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o434.
Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 55, 845-852.
Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3208.
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