Crystal structure of S-hexyl (E)-3-(2-hy-droxy-benzyl-idene)di-thio-carbazate.

R Miyatake,M S Begum,E Zangrando,M C Sheikh,M B H Howlader

doi:10.1107/s2056989016001857

Abstract

The title compound, C14H20N2OS2 [systematic name: S-hexyl (E)-2-(2-hy-droxy-benzyl-idene)hydrazine-1-carbodi-thio-ate], crystallizes with four independent mol-ecules (A-D) in the asymmetric unit. All four mol-ecules adopt an E conformation with respect to the C=N bond of the benzyl-idene moiety and have an intra-molecular O-H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, the A and D mol-ecules are connected by a pair N-H⋯S hydrogen bonds, forming a dimer with an R 2 (2)(8) ring motif. In the case of mol-ecules B and C, they are linked to themselves by pairs of N-H⋯S hydrogen bonds, forming B-B and C-C inversion dimers with R 2 (2)(8) ring motifs.

Highlights

The title compound, C14H20N2OS2 [systematic name: S-hexyl (E)-2-(2-hydroxybenzylidene)hydrazine-1-carbodithioate], crystallizes with four independent molecules (A–D) in the asymmetric unit
The A and D molecules are connected by a pair N—HÁ Á ÁS hydrogen bonds, forming a dimer with an R22(8) ring motif
As part of our ongoing structural studies of S-containing Schiff bases, we report on the structure of a molecule having a hexyl chain, similar to other ligands reported by our group (Begum, Zangrando et al, 2015; Begum, Howlader, Miyatake et al, 2015; Howlader et al, 2015) but differing in their ability to act as tridentate ligands in metal coordination (Begum, Howlader, Sheikh et al, 2015)

Summary

Chemical context

Bidentate Schiff bases of S-methyl or S-benzyl dithiocarbazates and their metal complexes have received considerable attention for their possible bioactivities (Chan et al, 2008; How et al, 2008; Zangrando et al, 2015; Ali et al, 2002; Chew et al, 2004; Crouse et al, 2004). As part of our ongoing structural studies of S-containing Schiff bases, we report on the structure of a molecule having a hexyl chain, similar to other ligands reported by our group (Begum, Zangrando et al, 2015; Begum, Howlader, Miyatake et al, 2015; Howlader et al, 2015) but differing in their ability to act as tridentate ligands in metal coordination (Begum, Howlader, Sheikh et al, 2015)

Structural commentary

Refinement