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

Abstract

The asymmetric unit of the title compound, C15H15NO3S, contains two independent mol­ecules. The conformations of the N—C bonds in the C—SO2—NH—C(O) segments have gauche torsions with respect to the SO bonds. Further, the mol­ecules are twisted at the S atoms with torsion angles of −53.1 (2) and 61.2 (2)° in the two mol­ecules. The dihedral angles between the sulfonyl benzene rings and the —SO2—NH—C—O segments are 86.0 (1) and 87.9 (1)°. Furthermore, the dihedral angles between the sulfonyl and the benzoyl benzene rings are 88.1 (1) and 83.5 (1)° in the two mol­ecules. In the crystal, mol­ecules are linked by N—H⋯O(S) hydrogen bonds.

Monomer spectroscopic analysis and dimer interaction energies on N-(4-methoxybenzoyl)-2-methylbenzenesulfonamide by experimental and theoretical approaches

“…Mean values of the C-H bond distances have been also calculated at 1.083 Å (B3LYP), 1.074 Å (HF) and 1.084 Å (B3LYP), 1.076 Å (HF) in phenylene and methylphenyl ring, respectively. For a similar benzene sulfonamide derivative, 2-Methyl-N-(4-methylbenzoyl) benzene sulfonamide, mean C-C values in methylphenyl ring have been reported 1.379 Å byGowda et al[39]. S1-N1 bond length that the sulfonyl connected to amine group has been computed values of 1.718Å (DFT) and 1.663Å (HF) in this study.…”

4-Iodo-N-(o-tolylsulfonyl)benzamide

“…1, contains two molecules [A (N1) and B N2)], similar to the situation observed for N-(4-chlorobenzoyl)-2-methylbenzenesulfonamide (Suchetan et al, 2010b) and N-(4-methylbenzoyl)-2-methylbenzenesulfonamide (Gowda et al, 2010). However, in the crystal structures of N-(benzoyl)-2-methylbenzenesulfonamide (Suchetan et al, 2010a) and N-(4-nitrobenzoyl)-2-methylbenzenesulfonamide (Suchetan et al, 2011), there is only one molecule in the asymmetric unit.…”

“…Further, N-(arylsulfonyl)-arylamides are known as potent antitumour agents against a broad spectrum of human tumour xenografts (colon, lung, breast, ovary and prostate) in nude mice (Mader et al, 2005). In view of the importance of N-(arylsulfonyl)-arylamides and in continuation of our work on the synthesis and crystal structures of N-(2-methylphenylsulfonyl)-arylamides (Suchetan et al, 2010a,b;Gowda et al, 2010;Suchetan et al, 2011), the title compound was synthesized and we report herein on its crystal structure.…”

N-(4-Chlorobenzoyl)-2-methylbenzenesulfonamide

“…For background literature and similar structures, see: Gowda et al (2010); Suchetan et al (2010a,b,c). = 84.254 (9) V = 1418.0 (2) Å 3 Z = 4 Mo K radiation = 0.42 mm À1 T = 299 K 0.38 Â 0.24 Â 0.14 mm…”