2,4-Dimethyl-N-phenylbenzenesulfonamide

Abstract

The asymmetric unit of the crystal structure of the title compound, C14H15NO2S, contains two mol­ecules. The conformations of the N—C bonds in the C—SO2—NH—C segments of the structure have trans and gauche torsion angles with the S=O bonds. Furthermore, the torsion angles of the C—SO2—NH—C groups in the two mol­ecules are 46.1 (3) (glide image of mol­ecule 1) and 47.7 (3)° (mol­ecule 2). The ortho-methyl groups in the sulfonyl benzene ring are oriented away from the S=O bonds. The two benzene rings are tilted relative to each other by 67.5 (1) and 72.9 (1)° in the two mol­ecules. N—H⋯O and C—H⋯O hydrogen bonds pack the mol­ecules into one-dimensional chains in different directions, resulting in a two-dimensional network.

4-Chloro-2-methyl-N-(2-methylphenyl)benzenesulfonamide

“…The two benzene rings are tilted relative to each other by 45.8 (1)°, compared with the values of 86.6 (2)° (molecule 1) and 83.0 (2)° (molecule 2), in the two independent molecules of 4-chloro-2-methyl-N-(phenyl)benzenesulfonamide (Gowda et al, 2009a). The other bond parameters in the title compound are similar to those observed in 2,4-dimethyl-N-(phenyl)benzenesulfonamide (Gowda et al, 2009b) and other aryl sulfonamides (Perlovich et al, 2006;Gelbrich et al, 2007). The crystal packing of the molecules is characterized by N-H…”

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

“…1). The molecule is bent at the S atom with the C-SO 2 -NH-C torsion angle of -69.7 (2)°, compared to the values of -48.2 (2)° in 2,4-dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide (II) (Gowda et al, 2009b), and 46.1 (3)° and 47.7 (3)° in the two independent molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (III) (Gowda et al, 2009a).…”

“…BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship. As part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides (Gowda et al, 2008(Gowda et al, , 2009a, in the present work, the structure of 2,4-dimethyl-N-(3,4-dichlorophenyl)benzenesulfonamide (I) has been determined. The conformations of the N-C bond in the C-SO 2 -NH-C segment are trans and gauche to the S=O bonds (Fig.…”

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

“…For related structures, see: Gowda et al (2008Gowda et al ( , 2009a. For comparative bond lengths in other aryl sulfonamides, see: Gelbrich et al (2007); Perlovich et al (2006).…”

“…BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship. In the present work, as part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides (Gowda et al, 2008;Gowda et al, 2009a;Gowda et al, 2009b), the structure of 2,4-dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide has been determined. The conformations of the N-C bonds in the C-SO 2 -NH-C segment have trans and gauche torsion angles with the S=O bonds ( Fig.…”