N-(2-Methylphenyl)benzenesulfonamide

Abstract

Key indicators: single-crystal X-ray study; T = 299 K; mean (C-C) = 0.004 Å; R factor = 0.040; wR factor = 0.106; data-to-parameter ratio = 12.8.In the title compound, C 13 H 13 NO 2 S, the conformation of the N-H bond is anti to the ortho-methyl group on the aniline ring, in contrast to the syn conformation observed with respect to the ortho-chloro group in N-(2-chlorophenyl)-benzenesulfonamide. The dihedral angle between the two benzene rings is 61.5 (1) . Molecules are linked into chains running along the a axis by N-HÁ Á ÁO hydrogen bonds. Related literature

N-(2,6-Dimethylphenyl)benzenesulfonamide

“…The the N-H bond is trans to one of the S-O double bonds ( Fig. 1), similar to what is observed in N-(2-methylphenyl)-benzenesulfonamide (N2MPBSA) (Gowda et al, 2008) and other aryl sulfonamides (Perlovich et al, 2006;Gelbrich et al, 2007;). The two aromatic rings are rotated relative to each other by 44.9 (1)°, compared with the value of 61.5 (1)° in N2MPBSA.…”

“…The two aromatic rings are rotated relative to each other by 44.9 (1)°, compared with the value of 61.5 (1)° in N2MPBSA. The other bond parameters in N26DMPBSA are similar to those observed in N2MPBSA and other N-(aryl)-sulfonamides (Gowda, Babitha et al, 2007;Gowda, Foro et al 2007;Gowda et al 2008;Perlovich et al, 2006;Gelbrich et al, 2007) (Table 1) is shown in Fig. 2.…”

“…As part of a study of the substituent effects on the crystal structures of N-(aryl)-sulfonamides, in the present work, the structure of N-(2,6-dimethylphenyl)-benzenesulfonamide (N26DMPBSA) has been determined (Gowda et al, 2005(Gowda et al, , 2008Gowda, Babitha et al 2007;Gowda, Foro et al 2007). The the N-H bond is trans to one of the S-O double bonds ( Fig.…”

N-(2,3-Dimethylphenyl)benzenesulfonamide

“…The amino H atom is trans to one of the O atoms of the SO 2 group (Fig. 1), similar to that observed in N-(2,6-dimethylphenyl)-benzenesulfonamide (Gowda et al, 2008a), N-(2-methylphenyl)-benzenesulfonamide (Gowda et al, 2008b) and other aryl sulfonamides (Perlovich et al, 2006;Gelbrich et al, 2007;Gowda et al, 2008c). The two benzene rings are tilted relative to each other by 64.8 (1)°, compared with the values of 44.9 1…”

“…BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship. In the present work, as part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al, 2008a(Gowda et al, , 2008b(Gowda et al, , 2008c, the structure of N-(2,3-dimethylphenyl)-benzenesulfonamide has been determined.…”