Abstract
In the title compound, C16H13Cl2N3O3S2, 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 S(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 R22(8) and R12(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.
Highlights
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 molecular conformation is stabilized by intramolecular C—HÁ Á ÁCl and C— HÁ Á ÁN hydrogen bonds, forming rings with graph-set notation S(5)
Pairs of molecules are linked by N—HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds, forming inversion dimers with graph-set notation R22(8) and R21(11), which are connected by C—HÁ Á ÁO hydrogen-bonding interactions into ribbons parallel to (100)
Summary
The pyrazole core structure has been widely used as a common heterocyclic scaffold in medicinal chemistry to produce novel drug candidates with a great variety of pharmacological activities including anti-inflammatory, antiplatelet, anticancer, antimycobacterial, antidepressant and anticonvulsant properties (Kuc ̧ukguzel & Senkardes, 2015; Calıskan et al, 2013; Ding et al, 2009; Baraldi et al, 2004; Palaska et al, 2008). Pyrazole-carboxamide derivatives have been shown to exhibit antimycobacterial, antifungal and antiviral activities (Sun & Zhou, 2015; Yan et al, 2018; Comber et al, 1992). We report the crystallographic characterization and Hirshfeld surface analysis of one of these compounds bearing the 2,4dichlorobenzyl substituent at one of the pyrazole nitrogen atoms
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