Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-fluorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide

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 thiazolidine ring makes dihedral angles of 13.51 (14), 48.6 (3) and 76.5 (3)° with the fluorophenyl ring and the major- and minor-disorder components of the phenyl ring, respectively. The central thiazolidine 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%) interactions.

Keywords

• crystal structure
• charge assisted hydrogen bonding
• thiazolidine ring
• disorder
• Hirshfeld surface analysis.