Title of article :
Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-chlorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide
Author/Authors :
Duruskari, Gulnara Sh. Organic Chemistry Department - Baku State University, Azerbaijan , Khalilov, Ali N. Organic Chemistry Department - Baku State University, Azerbaijan , Akkurt, Mehmet Department of Physics - Faculty of Sciences - Erciyes University, Turkey , Mammadova, Gunay Z. Organic Chemistry Department - Baku State University, Azerbaijan , Chyrka, Taras Department of Theoretical and Industrial Heat Engineering (TPT) - National Technical University of Ukraine "Igor Sikorsky Kyiv Polytechnic Institute", Ukraine , Maharramov, Abel M. Organic Chemistry Department - Baku State University, Azerbaijan
Abstract :
The title salt, C16H15ClN3S+·Br−, is isotypic with (E)-3-[(4-fluorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide [Khalilov et al. (2019[Khalilov, A. N., Atioğlu, Z., Akkurt, M., Duruskari, G. S., Toze, F. A. A. & Huseynova, A. T. (2019). Acta Cryst. E75, 662-666.]). Acta Cryst. E75, 662–666]. In the cation of the title salt, the atoms of the phenyl ring attached to the central thiazolidine ring and the atom joining the thiazolidine ring to the benzene ring are disordered over two sets of sites with occupancies of 0.570 (3) and 0.430 (3). The major and minor components of the disordered thiazolidine ring adopt slightly distorted envelope conformations, with the C atom bearing the phenyl ring as the flap atom. 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 contacts into chains parallel to the a axis. Furthermore, not existing in the earlier report of (E)-3-[(4-fluorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide, C—H⋯π interactions and π–π stacking interactions [centroid-to-centroid distance = 3.897 (2) Å] between the major components of the disordered phenyl ring contribute to the stabilization of the molecular packing. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions for the crystal packing are from H⋯H (30.5%), Br⋯H/H⋯Br (21.2%), C⋯H/H⋯C (19.2%), Cl⋯H/H⋯Cl (13.0%) and S⋯H/H⋯S (5.0%) interactions.
Keywords :
crystal structure. , Hirshfeld surface analysis , isotypic , charge-assisted hydrogen bonding , thiazolidine ring , disorder
Journal title :
Acta Crystallographica Section E: Crystallographic Communications