N-(3,4-Dichlorophenyl)-4-methylbenzenesulfonamide

K Shakuntala,B Thimme Gowda,Sabine Foro

doi:10.1107/s1600536810051305

K Shakuntala, B Thimme Gowda + Show 1 more

Open Access

https://doi.org/10.1107/s1600536810051305

Copy DOI

Abstract

In the title compound, C13H11Cl2NO2S, the conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S=O bonds. The molecule is bent at the S atom with a C—SO2—NH—C torsion angle of 64.3 (4)°. Furthermore, the conformation of the N—H bond and the meta-chloro group in the adjacent benzene ring are anti to each other. The two benzene rings are tilted relative to each other by 82.5 (1)°. In the crystal, molecules are linked by pairs of N—H⋯O(S) hydrogen bonds, forming inversion dimers.

Highlights

In the title compound, C13H11Cl2NO2S, the conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S O bonds
The molecule is bent at the S atom with a C—SO2—NH—C torsion angle of 64.3 (4)
Molecules are linked by pairs of N—HÁ Á ÁO(S) hydrogen bonds, forming inversion dimers

Summary

Structure Reports Online

Key indicators: single-crystal X-ray study; T = 299 K; mean (C–C) = 0.008 A; R factor = 0.086; wR factor = 0.236; data-to-parameter ratio = 14.0. C13H11Cl2NO2S, the conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S O bonds. The molecule is bent at the S atom with a C—SO2—NH—C torsion angle of 64.3 (4). The conformation of the N—H bond and the meta-chloro group in the adjacent benzene ring are anti to each other. The two benzene rings are tilted relative to each other by 82.5 (1). Molecules are linked by pairs of N—HÁ Á ÁO(S) hydrogen bonds, forming inversion dimers. Related literature For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al (2009); Shakuntala et al (2010, 2011); For related structures, see: Gelbrich et al (2007); Perlovich et al (2006)

HÁ Á ÁA

Special details