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

ABSTRACT: In the cation of the title salt, C16H14Cl2N3S+·Br-, the central thia-zolidine ring adopts an envelope conformation. The phenyl ring is disordered over two sites with a refined occupancy ratio of 0.541 (9):0.459 (9). In the crystal, C-H⋯Br and N-H⋯Br hydrogen bonds link the components into a three-dimensional network with the cations and anions stacked along the b-axis direction. Weak C-H⋯π inter-actions, which only involve the minor disorder component of the ring, also contribute to the mol-ecular packing. In addition, there are also inversion-related Cl⋯Cl halogen bonds and C-Cl⋯π (ring) contacts. A Hirshfeld surface analysis was conducted to verify the contributions of the different inter-molecular inter-actions.

SUBMITTER: Akkurt M

PROVIDER: S-EPMC6072981 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-3-[(4-chloro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide.

Project description:The title salt, C16H15ClN3S+·Br-, is isotypic with (E)-3-[(4-fluoro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide [Khalilov et al. (2019 ▸). Acta Cryst. E75, 662-666]. In the cation of the title salt, the atoms of the phenyl ring attached to the central thia-zolidine ring and the atom joining the thia-zolidine 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 thia-zolidine 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-fluoro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide, C-H⋯π inter-actions and π-π stacking inter-actions [centroid-to-centroid distance = 3.897 (2) Å] between the major components of the disordered phenyl ring contribute to the stabilization of the mol-ecular 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%) inter-actions.

| S-EPMC6690452 | biostudies-literature

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