N-(2,3-Dichlorophenyl)-4-methylbenzenesulfonamide

Abstract

The title compound, C13H11Cl2NO2S, contains two molecules in the asymmetric unit in which the dihedral angles between the benzene rings are 76.0 (1) and 79.9 (1)°. The conformations of the N—H bonds with respect to their adjacent ortho-chlorine atoms are syn. In the crystal, N—H⋯O hydrogen bonds link the molecules into dimers.

N-(2,4-Dichlorophenyl)-4-methylbenzenesulfonamide

“…The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our work on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al, 2004;Gowda et al, 2000Gowda et al, , 2006, N-(aryl)-methanesulfonamides (Gowda et al, 2007) and N-(aryl)-arylsulfonamides (Shakuntala et al, 2010), in the present work, the crystal structure of N-(2,4-dichlorophenyl)-4-methylbenzenesulfonamide (I) has been determined ( Fig. 1).…”

“…The conformation of the N-H bond in the C-SO 2 -NH-C segment and the ortho-chloro group in the anilino benzene ring are syn to each other. The molecule is bent at the S atom with the C-SO 2 -NH-C torsion angle of -69.1 (2)°, compared to the values of 65.4 (2) and -61.7 (2)° in the two molecules of N-(2,3-dichlorophenyl)-4-methylbenzenesulfonamide (II) (Shakuntala et al, 2010).…”

“…For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al (2004); Gowda et al (2000Gowda et al ( , 2006, on N-(aryl)methanesulfonamides, see: Gowda et al (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al (2007); Perlovich et al (2006); Shakuntala et al (2010). For the preparation of the title compound, see: Shetty & Gowda (2005) Experimental Crystal data C 13 H 11 Cl 2 NO 2 S M r = 316.19 Monoclinic, P2 1 =c a = 11.385 (1) Å b = 11.959 (1) Å c = 11.428 (1) Å = 112.87 (2) V = 1433.6 (2) Å 3 Z = 4 Mo K radiation = 0.59 mm À1 T = 293 K 0.44 Â 0.38 Â 0.28 mm…”

N-(2,6-Dichlorophenyl)-4-methylbenzenesulfonamide

“…In the present work, as part of a study of the substituent effects on the crystal structures of N-(aryl)arylsulfonamides (Gowda et al, 2009;Nirmala et al, 2010;Shakuntala et al, 2010), the structure of N-(2,6-dichlorophenyl)-4-methylbenzenesulfonamide (I) has been determined (Fig. 1).…”

“…For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al (2009); ; Shakuntala et al (2010). For related structures, see: Gelbrich et al (2007); Perlovich et al (2006).…”