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

Mehmet Akkurt,Gulnara Sh Duruskari,Abel M Maharramov,Flavien A A Toze,Ali N Khalilov

doi:10.1107/s2056989018011155

Abstract

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) Å and 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.

Highlights

In the cation of the title salt, C15H15N4S+ÁBrÀÁH2O, the central thiazolidine ring adopts an envelope conformation with puckering parameters Q(2) = 0.279 (4) Aand ’(2) = 222.5 (9)
The cations, anions and water molecules are linked into a three-dimensional network, which forms cross layers parallel to the (120) and (120) planes via O—HÁ Á ÁBr, N—HÁ Á ÁBr and N—HÁ Á ÁN hydrogen bonds
Hirshfeld surface analysis and 2D fingerprint plots indicate that the most important contributions to the crystal packing are from HÁ Á ÁH (35.5%), CÁ Á ÁH/HÁ Á ÁC (23.9%), BrÁ Á ÁH/HÁ Á ÁBr (16.4%), NÁ Á ÁH/HÁ Á ÁN (10.6%) and SÁ Á ÁH/HÁ Á ÁS (7.9%) interactions

Summary

Chemical context

Schiff bases and related hydrazone compounds play an important role in coordination and medicinal chemistry due to their high coordination ability (Mahmoudi et al, 2017a,b,c; Mitoraj et al, 2018; Shixaliyev et al, 2013a), application of those metal complexes in catalysis (Jlassi et al, 2014; Gurbanov et al, 2018; Mahmudov et al, 2014; Shixaliyev et al, 2013b, 2014), biological properties (Abedi et al, 2014), etc. We found strong O—HÁ Á ÁBrÀ and N+—HÁ Á ÁBrÀ types of chargeassisted hydrogen bonds in (E)-5-phenyl-3-[(pyridin-4-ylmethylidene)amino]thiazolidin-2-iminium bromide monohydrate

Structural commentary

Supramolecular features and Hirshfeld surface analysis

Database survey

Synthesis and crystallization

Findings

C14 H14A C15 H15A