A nimesulide derivative with potential anti-inflammatory activity: Synthesis, X-ray powder structure analysis and DFT study

A nimesulide derivative, N-[4-(2,5-dioxo-2,5-dihydropyrrol-1-yl)-2-phenoxyphenyl]methanesulfonamide (2), was synthesized and its crystal structure has been determined from X-ray powder diffraction data following direct-space global optimization technique and refined by the Rietveld method. The molecular geometry and electronic structure of the title compound were calculated at the DFT level using the hybrid exchange–correlation functional, BLYP. The optimized molecular geometry of 2 corresponds closely to that obtained from the X-ray structure analysis. Intermolecular N–H···O and C–H···O hydrogen bonds in 2 form one-dimensional polymeric chains of R22(8) rings propagating along the [1 0 0] direction. Further linking between parallel chains via C–H···π (arene) hydrogen bonds generates a two-dimensional supramolecular assembly in the (1 1 0) plane. The title compound exhibits potential anti-inflammatory activity and can induce 64% edema inhibition in rat paws.