Abstract
The structures of 2-[(2,3-dimethylphenyl)carbamoyl]benzenesulfonamide, 2-[(3,4-dimethylphenyl)carbamoyl]benzenesulfonamide and 2-[(2,6-dimethylphenyl)carbamoyl]benzenesulfonamide, all C(15)H(16)N(2)O(3)S, are stabilized by extensive intra- and intermolecular hydrogen bonds. In all three structures, the sulfonamide and carbamoyl groups are involved in hydrogen bonding. In the 2,3-dimethyl and 2,6-dimethyl derivatives, dimeric units and chains of molecules are formed parallel to the c axis. In the 3,4-dimethyl derivative, the hydrogen bonding creates tetrameric units, resulting in macrocyclic R(4)(4)(22) rings that form sheets in the ab plane. The three analogues are closely related to the fenamate class of nonsteroidal anti-inflammatory drugs.