Crystal structure and Hirshfeld surface analysis of 1-(2,4-di-chloro-benz-yl)-5-methyl--(thio-phene-2-sulfon-yl)-1-pyrazole-3-carboxamide.

Abstract

In the title compound, CHClNOS, the thio-phene ring is disordered in a 0.762 (3):0.238 (3) ratio by an approximate 180° rotation of the ring around the S-C bond linking the ring to the sulfonyl unit. The di-chloro-benzene group is also disordered over two sets of sites with the same occupancy ratio. The mol-ecular conformation is stabilized by intra-molecular C-H⋯Cl and C-H⋯N hydrogen bonds, forming rings with graph-set notation (5). In the crystal, pairs of mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming inversion dimers with graph-set notation (8) and (11), which are connected by C-H⋯O hydrogen-bonding inter-actions into ribbons parallel to (100). The ribbons are further connected into a three-dimensional network by C-H⋯π inter-actions and π-π stacking inter-actions between benzene and thio-phene rings, with centroid-to-centroid distances of 3.865 (2), 3.867 (7) and 3.853 (2) Å. Hirshfeld surface analysis has been used to confirm and qu-antify the supra-molecular inter-actions.