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

Rodrigues, V.Z.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811037767

Volume 67
Part 10
Page o2691
October 2011

Received 14 September 2011
Accepted 15 September 2011
Online 20 September 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.038
wR = 0.107
Data-to-parameter ratio = 16.7
Details

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

Vinola Z. Rodrigues,^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, C₁₄H₁₃Cl₂NO₂S, the N-H bond in the C-SO₂-NH-C segment orients itself away from the two ortho-methyl groups in the aniline benzene ring and towards the ortho-chloro group of the sulfonyl benzene ring. The molecule is bent at the S atom with a C-SO₂-NH-C torsion angle of -100.48 (18)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 69.6 (1)°. Intermolecular N-HO hydrogen bonds link the molecules into infinite chains.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006). For the hydrogen-bonding preferences of sulfonamides, see: Adsmond & Grant (2001). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004); Gowda et al. (2001); of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007); and of N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Gowda et al. (2003); Rodrigues et al. (2011).

Experimental

Crystal data

C₁₄H₁₃Cl₂NO₂S
M_r = 330.21
Monoclinic, P 2₁ /n
a = 12.021 (1) Å
b = 7.5458 (7) Å
c = 16.837 (1) Å
= 92.324 (7)°
V = 1526.0 (2) Å³
Z = 4
Mo K radiation
= 0.56 mm^-1
T = 293 K
0.40 × 0.36 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.807, T_max = 0.877
6113 measured reflections
3107 independent reflections
2188 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.107
S = 1.03
3107 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.83 (2)	2.14 (2)	2.891 (2)	152 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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: BQ2306 ).

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi for the award of an RFSMS fellowship.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.
Arjunan, V., Mohan, S., Subramanian, S. & Gowda, B. T. (2004). Spectrochim. Acta Part A, 60, 1141-1159.
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.
Gowda, B. T., D'Souza, J. D. & Kumar, B. H. A. (2003). Z. Naturforsch. Teil A, 58, 51-56.
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.
Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386-394.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.
Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2649.
Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 61, 600-606.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds