Insights into the nature of weak noncovalent interactions in 3-(4-fluoropheny1)-6-(2-fluoropheny1)-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole, a potential bioactive agent: X-ray, QTAIM and molecular docking analysis

A thorough examination of weak interactions present in the crystal structure of the title compound was investigated. Intramolecular C-H center dot center dot center dot N and F center dot center dot center dot S interactions make the molecule as fused 6,5,5,5,6,6-membered ring system. Two of the closely related structures show 1D-isostructurality with the title compound. The crystal structure is stabilized by different types of weak intermolecular C-H center dot center dot center dot N, C-H center dot center dot center dot F, C-H center dot center dot center dot pi and S center dot center dot center dot pi and pi center dot center dot center dot pi interactions. The first two strongest dimers are stabilized by stacking interactions. The nature of these interactions and their role was established through quantum theory of atoms-in-molecules approach. The Hirshfeld surface analysis clearly reveals that the para-substituted fluorine substantially change the contribution of intermolecular H center dot center dot center dot H and H center dot center dot center dot C contacts. The molecular docking analysis suggests that the title compound shows anti-inflammatory activity and selective against cyclooxygenase-1 (COX-1) enzyme and the 2-fluorophenyl and triazole moieties of the title compound are involved in the pi center dot center dot center dot pi interactions with active site aromatic residues. (C) 2019 Elsevier B.V. All rights reserved.