2-Methyl-N-(3-methylbenzoyl)benzenesulfonamide

Abstract

In the title compound, C15H15NO3S, the sulfonyl and amide-bound benzene rings are oriented at dihedral angles of 83.1 (1) and 22.5 (3)°, respectively, with the almost planar S—N—C=O segment (r.m.s. deviation = 0.003 Å). The dihedral angle between the two benzene rings is 74.8 (1)°. In the crystal structure, pairs of mol­ecules are linked into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds.

2-Methyl-N-(4-methylbenzoyl)benzenesulfonamide

“…The conformations of the N-C bonds in the C-SO 2 -NH-C(O) segments have gauche torsions with respect to the SO bonds. Further, the conformations of the N-H bonds in the C-SO 2 -NH-C(O) segments are anti to the C=O bonds, similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al, 2009), 2-methyl-N-(3-methylbenzoyl)benzenesulfonamide (III) (Gowda et al, 2010) and N-(4-chlorobenzoyl)4-methyl-benzenesulfonamide (IV) .…”

2-Methyl-N-(2-methylbenzoyl)benzenesulfonamide

“…As part of a study of the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al, 2010a,b;Suchetan et al, 2010), in the present work, the structure of 2-methyl-N-(2-methylbenzoyl)benzenesulfonamide (I) has been determined ( Fig.1). The conformation of the N-H bond in the S-NH-C═O segment of the structure is anti to the C═O bond, similar to that observed in 2-methyl-N-(3-methylbenzoyl)benzenesulfonamide (II) (Gowda et al, 2010a), 2-methyl-N-(4-methylbenzoyl)-benzenesulfonamide (III) (Gowda et al, 2010b) and 2-chloro-N-(2-chlorobenzoyl)benzenesulfonamide (IV) (Suchetan et al, 2010).…”

N-(3-Methoxybenzoyl)-2-methylbenzenesulfonamide

“…This is similar to what is observed in N-(benzoyl)-2-methylbenzenesulfonamide (II, Suchetan et al, 2010), N-(3-chlorobenzoyl)-2-methylbenzenesulfonamide (III, Suchetan et al, 2011) and N-(3-methylbenzoyl)-2-methylbenzenesulfonamide (IV, . Similarly, the conformation between the N-H bond and the meta-methoxy group in the benzoyl ring is syn, also similar to the conformation in III (Suchetan et al, 2011) and IV (Gowda et al, 2010). Table 1,…”

“…For similar structures, see: Gowda et al (2010); Suchetan et al (2010Suchetan et al ( , 2011. Table 1 Hydrogen-bond geometry (Å , ).…”