Crystal structure and Hirshfeld surface analysis of 1-(2,4-dichlorobenzyl)-5-methyl-N-(thiophene-2-sulfonyl)-1H-pyrazole-3-carboxamide

Abstract

In the title compound, C16H13Cl2N3O3S2, the thiophene 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 dichlorobenzene group is also disordered over two sets of sites with the same occupancy ratio. The molecular conformation is stabilized by intramolecular C—H...Cl and C—H...N hydrogen bonds, forming rings with graph-set notation S(5). In the crystal, pairs of molecules are linked by N—H...O and C—H...O hydrogen bonds, forming inversion dimers with graph-set notation R22(8) and R12(11), which are connected by C—H...O hydrogen-bonding interactions into ribbons parallel to (100). The ribbons are further connected into a three-dimensional network by C—H...π interactions and π–π stacking interactions between benzene and thiophene 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 quantify the supramolecular interactions.

Keywords

• crystal structure
• dimer
• 1H-pyrazole ring
• thiophene ring
• disorder
• hydrogen-bonding patterns