N-(2-Methylphenyl)methanesulfonamide

Abstract

The conformation of the N—H bond in the structure of the title compound (2MPMSA), C8H11NO2S, is syn to the ortho-methyl substituent, in contrast with the anti conformation observed for the meta-methyl-substituted compound (3MPMSA). The ortho substitution of the methyl group in N-phenyl­methane­sulfonamde (PMSA) changes its space group from monoclinic P21/c to triclinic P\overline{1}, compared with the change from monoclinic P21/c to ortho­rhom­bic Pccn on meta-substitution. The bond parameters in PMSA, 2MPMSA and 3MPMSA are similar, except for the torsion angles involving the S—N bond. The N—H H atom alone lies on one side of the plane of the phenyl group, while the whole methane­sulfonyl group is on the opposite side of the plane, similar to what was observed in PMSA and 3MPMSA. Thus, the amide H atom is available to a receptor mol­ecule during biological activity. The mol­ecules of the title compound form centrosymmetric dimers via an N—H⋯O(sulfon­yl) hydrogen bond.