Crystal structure of (E)- N-cyclo-hexyl-2-(2-hy-droxy-3-methyl-benzyl-idene)hydrazine-1-carbo-thio-amide

Acta Crystallogr E Crystallogr Commun. 2019 Jun 28;75(Pt 7):1065-1068. doi: 10.1107/S2056989019008946. eCollection 2019 Jul 1.

Abstract

The asymmetric unit of the title compound, C15H21N3OS, comprises of two crystallographically independent mol-ecules (A and B). Each mol-ecule consists of a cyclo-hexane ring and a 2-hy-droxy-3-methyl-benzyl-idene ring bridged by a hydrazinecarbo-thio-amine unit. Both mol-ecules exhibit an E configuration with respect to the azomethine C=N bond. There is an intra-molecular O-H⋯N hydrogen bond in each mol-ecule forming an S(6) ring motif. The cyclo-hexane ring in each mol-ecule has a chair conformation. The benzene ring is inclined to the mean plane of the cyclo-hexane ring by 47.75 (9)° in mol-ecule A and 66.99 (9)° in mol-ecule B. The mean plane of the cyclo-hexane ring is inclined to the mean plane of the thio-urea moiety [N-C(=S)-N] by 55.69 (9) and 58.50 (8)° in mol-ecules A and B, respectively. In the crystal, the A and B mol-ecules are linked by N-H⋯S hydrogen bonds, forming 'dimers'. The A mol-ecules are further linked by a C-H⋯π inter-action, hence linking the A-B units to form ribbons propagating along the b-axis direction. The conformation of a number of related cyclo-hexa-nehydrazinecarbo-thio-amides are compared to that of the title compound.

Keywords: Schiff base; crystal structure; hydrazinecarbo­thio­amide; inter­molecular inter­actions.

Grants and funding

This work was funded by Universiti Sains Malaysia grant 1001/PKIMIA/811269. The World Academy of Sciences grant . Shahjalal University of Science and Technology grant PS/2018/1/04, 2018–2019 to Md. A. Arafath. Malaysian Government grant MyBrain15 to H. C. Kwong.