Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-fluoro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide

Acta Crystallogr E Crystallogr Commun. 2019 Apr 18;75(Pt 5):662-666. doi: 10.1107/S2056989019004973. eCollection 2019 May 1.

Abstract

In the cation of the title salt, C16H15FN3S+·Br-, the phenyl ring is disordered over two sets of sites with a refined occupancy ratio of 0.503 (4):0.497 (4). The mean plane of the thia-zolidine ring makes dihedral angles of 13.51 (14), 48.6 (3) and 76.5 (3)° with the fluoro-phenyl ring and the major- and minor-disorder components of the phenyl ring, respectively. The central thia-zolidine ring adopts an envelope conformation. In the crystal, centrosymmetrically related cations and anions are linked into dimeric units via N-H⋯Br hydrogen bonds, which are further connected by weak C-H⋯Br hydrogen bonds into chains parallel to [110]. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (44.3%), Br⋯H/H⋯Br (16.8%), C⋯H/H⋯C (13.9%), F⋯H/H⋯F (10.3%) and S⋯H/H⋯S (3.8%) inter-actions.

Keywords: Hirshfeld surface analysis.; charge assisted hydrogen bonding; crystal structure; disorder; thia­zolidine ring.