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

• Main Authors: Md Yusof, Enis Nadia, Tiekink, Edward R. T., Jotani, Mukesh M., Simone, Michela I., Page, Alister J., Ravoof, Thahira Begum S. A.
• Format: Article
• Language: English
• Published: Elsevier 2018
• Online Access: http://psasir.upm.edu.my/id/eprint/74068/1/Synthesis%2C%20characterisation%20and%20structure%20determination%20of%203-%5B%281Z%29-%7B2-%20%5Bbis%28%7B%5B%282-methylphenyl%29methyl%5Dsulfanyl%7D%29methylidene%5Dhydrazin-1-%20ylidene%7Dmethyl%5Dbenzene-1%2C2-diol.pdf; http://psasir.upm.edu.my/id/eprint/74068/

A light-yellow crystalline product (1), which was isolated after one week from the filtrate of the reaction between S-2-methylbenzyldithiocarbazate and 2,3-dihydroxybenzaldehyde, 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-CH…N(imine) and tolyl-CH … π(tolyl) interactions; the importance of these contacts is indicated by a Hirshfeld surface analysis.