N-(4-Methylphenyl)-2-nitrobenzenesulfonamide

Abstract

In the crystal of the title compound, C13H12N2O4S, the conformation of the N—H bond in the –SO2—NH– segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The mol­ecule is twisted at the S—N bond with a torsion angle of 76.55 (18)°. The dihedral angle between the planes of the rings is 72.64 (8)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O(S) hydrogen bonds to form inversion dimers.

N-(2-Methylphenyl)-4-nitrobenzenesulfonamide

“…The conformation of the N-C bond in the -SO 2 -NH-C segment has gauche torsion with respect to the S═O bonds ( Fig.1). Further, the conformation of the N-H bond in the -SO 2 -NH-segment is syn to the ortho-methyl group in the anilino ring, compared to syn conformation observed between the N-H bond and ortho-nitro group in the sulfonyl benzene ring in N-(4-methylphenyl)-2-nitrobenzenesulfonamide (I) (Chaithanya et al, 2012). The molecule is twisted at the S-N bond with the torsional angle of -58.97 (21)°, compared to the value of 76.55 (18)° in (I).…”

“…For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al (2011); Bowes et al (2003); Gowda & Weiss (1994); Saeed et al (2010); Shahwar et al (2012), of N-arylsulfonamides, see: Chaithanya et al (2012); Gowda et al (2005) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).…”