2,4-Dichloro-N-(3,4-dimethyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536811038256

Volume 67
Part 10
Page o2712
October 2011

Received 16 September 2011
Accepted 19 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 17.0
Details

2,4-Dichloro-N-(3,4-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 title compound, C₁₄H₁₃Cl₂NO₂S, the C-SO₂-NH-C torsion angle is -60.84 (18). The sulfonyl and the aniline benzene rings are tilted relative to each other by 66.4 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-HO hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006). For hydrogen-bonding modes 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. (2000), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Gowda et al. (2005); Rodrigues et al. (2011).

Experimental

Crystal data

C₁₄H₁₃Cl₂NO₂S
M_r = 330.21
Monoclinic, P 2₁ /c
a = 7.8381 (6) Å
b = 14.778 (1) Å
c = 13.660 (1) Å
= 101.840 (9)°
V = 1548.59 (19) Å³
Z = 4
Mo K radiation
= 0.55 mm^-1
T = 293 K
0.46 × 0.44 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with 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 = 0.785, T_max = 0.843
6193 measured reflections
3155 independent reflections
2447 reflections with I > 2(I)
R_int = 0.011

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.105
S = 1.03
3155 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.83 (2)	2.17 (2)	2.945 (2)	154 (2)
Symmetry code: (i) -x, -y+1, -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: BT5644 ).

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., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.
Gowda, B. T., Kumar, B. H. A. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 721-728.
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, 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, submitted (ds2145).
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