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Three nimesulide derivatives, N-[4-(2,5-dioxo-pyrrolidin-1-yl)-2-phenoxyphenyl] methanesulfonamide (2), N-[4-(4-methanesulfonylamino-3-phenoxy phenylsulfamoyl) phenyl] acetamide (3), and 4-(4-methanesulfonylamino-3-phenoxyphenyl-carbamoyl)-butanoic acid (4), have been synthesized, and their crystal structures have been determined from laboratory powder X-ray diffraction data. The nature of intermolecular interactions in 2–4 has been analyzed through Hirshfeld surfaces and two-dimensional fingerprint plots and compared with that in the nimesulide polymorphs (1a and 1b). The crystal packing in 2–4 exhibits an interplay of N–H···O, O–H···O (in 4), C–H···O, and C–H···π (in 2) hydrogen bonds, which assemble molecules into a supramolecular framework. Hydrogen-bond based interactions in 2–4 have been complemented by calculating molecular electrostatic potential surfaces. In a competitive molecular recognition situation, the effectiveness of the -NH moiety as a hydrogen bond donor is comparable to that of the -COOH moiety in 4. Hirshfeld surface analyses of 2–4 as well as a few related nimesulide derivatives indicate that about 90% of the Hirshfeld surface areas in these compounds are due to H···H, C···H, and O···H contacts.

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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.

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