A series of three nimesulidetriazole derivatives, N-(2-phenoxy-4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl)methanesulfonamide (2), N-(2-phenoxy-4-(4-p-tolyl-1H-1,2,3-triazol-1-yl)phenyl)methanesulfonamide (3) and N-(4-(4-((4-chloro-3-methylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-2-phenoxyphenyl)methanesulfonamide (4), have been synthesized and the crystal structures of 2–4 containing more than twenty eight (28) non-hydrogen atoms in their chemical formulas and six (6) torsional degrees of freedom have been determined from laboratory X-ray powder diffraction data. The nature of intermolecular interactions in 2–4 has been analyzed through Hirshfeld surfaces and 2D fingerprint plots and compared with that in the nimesulide polymorphs (1a and 1b). The DFT optimized molecular geometries in 2–4 agree closely with those obtained from the crystallographic studies. The N(sulphonamide)–H⋯O(sulfonyl) hydrogen bonds generated cyclic R22(8) rings in 2–4, which are further connected through C–H⋯O, C–H⋯N hydrogen bonds and C–H⋯π interactions into a two-dimensional framework in 3 and a three-dimensional architecture in 2 and 4. Hirshfeld surface analyses of 1–4 as well as a few related nimesulide derivatives retrieved from the Cambridge Structural Database (CSD) indicate that about 80% of the Hirshfeld surface areas in this class of compounds are due to H⋯H, C⋯H and O⋯H contacts.
