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

In the crystal structure of the title compound, C15H17NO2S, the conformations of the N—C bond in the C—SO2—NH—C segment are trans and gauche, respectively, with respect to the S=O bonds. The molecule is bent at the S atom with a C—SO2—NH—C torsion angle of −61.8 (2)°. Furthermore, the conformation of the N—H bond and the 3-methyl group in the aniline benzene ring are nearly anti to each other. The dihedral angle between the benzene rings is 47.8 (1)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains.

In the crystal structure of the title compound, C 15 H 17 NO 2 S, the conformations of the N-C bond in the C-SO 2 -NH-C segment are trans and gauche, respectively, with respect to the S O bonds. The molecule is bent at the S atom with a C-SO 2 -NH-C torsion angle of À61.8 (2) . Furthermore, the conformation of the N-H bond and the 3-methyl group in the aniline benzene ring are nearly anti to each other. The dihedral angle between the benzene rings is 47.8 (1) . In the crystal, N-HÁ Á ÁO hydrogen bonds link the molecules into chains.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2240).

Comment
As part of our study of substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008a; 2009), in the present work, the structure of 4-methyl-N-(3,4-dimethylphenyl)benzenesulfonamide (N34DMP4MBSA) has been determined. The conformations of the N-C bond in the C-SO 2 -NH-C segment of the structure are "trans" and "gauche" with respect to the S=O bonds (Fig. 1). The molecule is bent at the S atom with the C-SO 2 -NH-C torsion angle of -61.8 (2). The conformation of the N-H bond and the meta-methyl group in the anilino benzene ring are nearly anti to each other. The two benzene rings in the title compound are tilted relative to each other by 47.8 (1)°. The other bond parameters in N34DMP4MBSA are similar to those observed in N-(2,6-dimethylphenyl)-benzenesulfonamide (Gowda et al., 2008a), N-(2,3-dimethylphenyl)-benzenesulfonamide (Gowda et al., 2009), N-(3,5-dichlorophenyl)-benzenesulfonamide (Gowda et al., 2008b)) and other aryl sulfonamides (Perlovich et al., 2006;Gelbrich et al., 2007). The N-H···O hydrogen bonds (Table 1) pack the molecules into infinite chains in the direction of a-axis (Fig. 2).

Experimental
The solution of toluene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly.
The residual 4-methylbenzenesulfonylchloride was treated with 3,4-dimethylaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 cc). The resultant 4-methyl-N-(3,4-dimethylphenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Shetty & Gowda, 2005). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement
The H atoms were positioned with idealized geometry using a riding model with C-H = 0.93-0.96 Å, N-H = 0.86 Å, and were refined with isotropic displacement parameters (set to 1.2 times of the U eq of the parent atom). For methyl group U iso (H) = 1.5 U eq . supplementary materials sup-2