A series of three nimesulidetriazole derivatives, N-IJ2-phenoxy-4-IJ4-phenyl-1H-1,2,3-triazol-1yl)phenyl)methanesulfonamide (2), N-IJ2-phenoxy-4-IJ4-p-tolyl-1H-1,2,3-triazol-1-yl)phenyl)methanesulfonamide(3) and N-IJ4-IJ4-IJIJ4-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) nonhydrogen 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 NIJsulphonamide)-H⋯OIJsulfonyl) hydrogen bonds generated cyclic R 2 2 (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.