Abstract

In the title compound, C16H10Cl2N2O2S, the dihedral angles formed by the chloro-substituted benzene rings with the central oxa-diazole ring are 6.54 (9) and 6.94 (8)°. In the crystal, C-H⋯N hydrogen bonding links the mol-ecules into undulating ribbons running parallel to the b axis. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H⋯C (18%), H⋯H (17%), H⋯Cl (16.6%), H⋯O (10.4%), H⋯N (8.9%) and H⋯S (5.9%) inter-actions.

Highlights

  • C—H N hydrogen bonding links the molecules into undulating ribbons running parallel to the b axis

  • Heterocyclic compounds are well known for their applications in agriculture (Jakobi et al, 1999) and for the synthesis of pharmaceuticals (Vitaku et al, 2014)

  • The title compound (Fig. 1) is an oxadiazole derivative containing two chlorophenyl substituents attached to a central oxadiazole thioethanone unit

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Summary

Chemical context

Heterocyclic compounds are well known for their applications in agriculture (Jakobi et al, 1999) and for the synthesis of pharmaceuticals (Vitaku et al, 2014). The wide range of applications and biological activities of this class of compounds is due to the presence of heteroatoms (N, O, S) in the molecule (Kashtoh et al, 2014). Oxadiazoles are among the most widely studied moieties of organic chemistry due to their many important chemical and biological properties including antimycobacterial (Jha et al., 2009), antioxidant (Fadda et al, 2011), anticancer (Zhang et al, 2011), antitumor (Loetchutinat et al, 2003), antimicrobial (Şahin et al, 2002), antifungal (Zou et al, 2002), anti-inflammatory (Palaska et al, 2002) and hypotensive (Tyagi & Kumar, 2002) activities. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level

Structural commentary
Supramolecular features
Synthesis and crystallization
Funding information
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