2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis

Abstract

The title dithiocarbazate ester, C16H16N2O2S2, comprises two almost planar residues, i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intramolecular hydroxy-O—H...N(imine) hydrogen bond, leading to an S(6) loop, is noted. An analysis of the geometric parameters is consistent with the molecule existing as the thione tautomer, and the conformation about the C=N bond is E. The thione S and imine H atoms lie to the same side of the molecule, facilitating the formation of intermolecular N—H...S hydrogen bonds leading to eight-membered {...HNCS}2 synthons in the crystal. These aggregates are connected by phenyl-C—H...O(hydroxy) interactions into a supramolecular layer in the bc plane; these stack with no directional interactions between them. An analysis of the Hirshfeld surface confirms the nature of the intermolecular interactions.

Keywords

• crystal structure
• hydrogen bonding
• dithiocarbazate ester
• Hirshfeld surface analysis