• 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

  • Pages
    11
  • From page
    1
  • To page
    11
  • 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
  • Serial Year
    2019
  • Record number

    2625405