2-[N-(2,3-Dimethylphenyl)carbamoyl]benzenesulfonamide and the 3,4- and 2,6-dimethylphenyl analogues.
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.
Siddiqui
Waseeq Ahmad
WA
Department of Chemistry, University of Sargodha, Pakistan.
Ahmad
Saeed
S
Siddiqui
Hamid Latif
HL
Parvez
Masood
M
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D003461:Crystallography; D019281:Dimerization; D054361:Fenamates / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*; D000096926:Benzenesulfonamides
D000894:Anti-Inflammatory Agents, Non-Steroidal; D001549:Benzamides; D054361:Fenamates; D013449:Sulfonamides; C531923:2-(N-(2,3-dimethylphenyl)carbamoyl)benzenesulfonamide; D000096926:Benzenesulfonamides; C531925:2-(N-(2,6-dimethylphenyl)carbamoyl)benzenesulfonamide; C531924:2-(N-(3,4-dimethylphenyl)carbamoyl)benzenesulfonamide