Crystal structure and Hirshfeld surface analysis of 1-(2-fluoro-phen-yl)-1 H-tetra-zole-5(4 H)-thione

Abstract

In the crystal of the title compound, C₇H₅FN₄S, the mol-ecules are non-planar, with dihedral angle formed by least-squares planes of tetra-zole and benzene rings of 59.94 (8) °. The crystal packing is formed by N-H⋯S hydrogen bonds, which link the mol-ecules into centrosymmetric dimers with an R ² ₂(8) ring motif, and by the offset face-to-face π-π stacking inter-actions between the benzene rings, which join the dimers into layers parallel to (100). The Hirshfeld surface analysis shows that the most important contributions to the surface contacts are from N⋯H/H⋯N (21.9%), S⋯H/H⋯S (21.1%), H⋯H (14.6%), F⋯H/H⋯F (11.8%) and C⋯H/H⋯C (9.5%) inter-actions.

Keywords: 1H-tetra­zole-5-thione ring; crystal structure; cyclo­addition products; hydrogen bonding; π–π stacking inter­actions.