A cinnamaldehyde Schiff base of -(4-methyl-benz-yl) di-thio-carbazate: crystal structure, Hirshfeld surface analysis and computational study.

The title di-thio-carbazate ester (I), CHNS [systematic name: ()-4-methyl-benzyl 2-[()-3-phenyl-allyl-idene]hydrazinecarbodi-thio-ate, comprises an almost planar central CNS residue [r.m.s. deviation = 0.0131 Å]. The methyl-ene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the mol-ecule approximates mirror symmetry with the 4-tolyl group bis-ected by the plane. The configuration about both double bonds in the N-N=C-C=C chain is ; the chain has an all conformation. In the crystal, eight-membered centrosymmetric thio-amide synthons, {⋯HNCS}, are formed N-H⋯S(thione) hydrogen bonds. Connections between the dimers C-H⋯π inter-actions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an inter-action profile similar to that of a closely related analogue with an -bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connected N-H⋯S hydrogen bonds is about 0.94 kcal mol more stable than that in (I).