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.

Gulnara Sh Duruskari,Abel M Maharramov,Sevim Türktekin Çelikesir,Ali N Khalilov,Gunay Z Mammadova,Anzurat A Akobirshoeva,Mehmet Akkurt

doi:10.1107/s2056989020012712

Abstract

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) Å and 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.

Highlights

Each cation is connected to two anions by N—HÁ Á Á Br hydrogen bonds, forming an R24(8) motif parallel to the (101) plane. van der Waals interactions between the cations, anions and N,Ndimethylformamide molecules further stabilize the crystal structure in three dimensions
The most important contributions to the surface contacts are from HÁ Á ÁH (55.6%), CÁ Á ÁH/HÁ Á ÁC (17.9%) and BrÁ Á ÁH/HÁ Á ÁBr (7.0%) interactions, as concluded from a Hirshfeld analysis
As part of our ongoing structural studies (Akkurt et al, 2018a,b; Khalilov et al, 2011, 2019), we report the crystal structure and Hirshfeld surface analysis of the title compound, (E)-3-[(4-methylbenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide N,N-dimethylformamide monosolvate

Summary

Chemical context

Sulfur and nitrogen-containing heterocyclic systems are of great interests in the fields of organic synthesis, drug design and material science (Abdelhamid et al, 2014; Pathania et al, 2019; Yin et al, 2020). In this context, thiazolidine derivatives play an important role in pharmaceutical and medicinal chemistry. Compounds incorporating thiazolidine and azomethine structural motifs have found applications in coordination chemistry, catalysis, crystal design and material science (Asadov et al, 2016; Akbari Afkhami et al, 2017; Maharramov et al, 2018; Mahmudov et al, 2019, 2020). As part of our ongoing structural studies (Akkurt et al, 2018a,b; Khalilov et al, 2011, 2019), we report the crystal structure and Hirshfeld surface analysis of the title compound, (E)-3-[(4-methylbenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide N,N-dimethylformamide monosolvate

Structural commentary

Supramolecular features

Hirshfeld surface analysis

Database survey

Findings

Synthesis and crystallization