Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-methyl-benzyl-idene)amino]-5-phenylthiazolidin-2-iminium bromide N,N-di-methyl-formamide monosolvate.

In the cation of the title salt, C17H18N3S+·Br-·C3H7NO, the central thia-zolidine ring adopts an envelope conformation with puckering parameters Q(2) = 0.310 (3) Šand φ(2) = 42.2 (6)°. In the crystal, each cation is connected to two anions by N-H⋯ Br hydrogen bonds, forming an R 4 2(8) motif parallel to the (10) plane. van der Waals inter-actions between the cations, anions and N,N-di-methyl-formamide mol-ecules further stabilize the crystal structure in three dimensions. The most important contributions to the surface contacts are from H⋯H (55.6%), C⋯H/H⋯C (17.9%) and Br⋯H/H⋯Br (7.0%) inter-actions, as concluded from a Hirshfeld analysis.

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

The central thia-zolidine ring of the title salt, C16H16N3S+·Br-, adopts an envelope conformation, with the C atom bearing the phenyl ring as the flap atom. In the crystal, the cations and anions are linked by N-H⋯Br hydrogen bonds, forming chains parallel to the b-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (46.4%), C⋯H/H⋯C (18.6%) and H⋯Br/Br⋯H (17.5%) inter-actions.

Crystal structure and Hirshfeld surface analysis of 3-amino-5-phenyl-thia-zolidin-2-iminium bromide.

In the cation of the title salt, C9H12N3S+·Br-, the thia-zolidine ring adopts an envelope conformation with the C atom adjacent to the phenyl ring as the flap. In the crystal, N-H⋯Br hydrogen bonds link the components into a three-dimensional network. Weak π-π stacking inter-actions between the phenyl rings of adjacent cations also contribute to the mol-ecular packing. A Hirshfeld surface analysis was conducted to qu-antify the contributions of the different inter-molecular inter-actions and contacts.

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

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.

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

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.

Crystal structure and Hirshfeld surface analysis of (E)-5-phenyl-3-[(pyridin-4-yl-methyl-idene)amino]-thia-zolidin-2-iminium bromide monohydrate.

In the cation of the title salt, C15H15N4S+·Br-·H2O, the central thia-zolidine ring adopts an envelope conformation with puckering parameters Q(2) = 0.279 (4) Šand φ(2) = 222.5 (9)°. The mean plane of the thia-zolidine ring makes dihedral angles of 12.4 (2) and 66.8 (3)° with the pyridine and phenyl rings, respectively. The pyridine ring in the title mol-ecule is essentially planar (r.m.s deviation = 0.005 Å). In the crystal, the cations, anions and water mol-ecules are linked into a three-dimensional network, which forms cross layers parallel to the (120) and (20) planes via O-H⋯Br, N-H⋯Br and N-H⋯N hydrogen bonds. C-H⋯π inter-actions also help in the stabilization of the mol-ecular packing. Hirshfeld surface analysis and 2D (two-dimensional) fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (35.5%), C⋯H/H⋯C (23.9%), Br⋯H/H⋯Br (16.4%), N⋯H/H⋯N (10.6%) and S⋯H/H⋯S (7.9%) inter-actions.

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

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.