Synthesis, characterisation and structure determination of 3-[(1Z)-{2-[bis({[(2-methylphenyl)methyl]sulfanyl})methylidene]hydrazin-1-ylidene}methyl]benzene-1,2-diol

Abstract

A light-yellow crystalline product (1), which was isolated after one week from the filtrate of the reaction between S-2-methylbenzyldithiocarbazate and 2,3dihydroxybenzaldehyde, was characterised by single crystal X-ray diffraction, FTIR and NMR spectroscopic analyses. The experimental molecular structure of 1 has been established by X-ray crystallography and showed, to a first approximation, a planar C2N2S2 + dihydroxyphenyl region that has an almost orthogonal relationship to the rings of the pendant S-bound benzyl groups. This structure has been verified via density functional theory calculations using the B3LYP/6311G(d,p) level of theory. The molecular packing featured linear supramolecular chains along the b-axis sustained by tolyl-C-H…N(imine) and tolyl-C-H…π(tolyl) interactions; the importance of these contacts is indicated by a Hirshfeld surface analysis.

Utilizing Hirshfeld surface calculations, non-covalent interaction (NCI) plots and the calculation of interaction energies in the analysis of molecular packing

“…in the crystal of 3- Fig. 3(a) (Yusof et al, 2018). As an example, the donor and the acceptors of intermolecular C-HÁ Á Á contacts can be recognized as blue and red regions A view of the Hirshfeld surface for (I) mapped over the calculated electrostatic potential in the range À0.077 to +0.056 atomic units (the red and blue regions represent negative and positive electrostatic potentials, respectively).…”