A cinnamaldehyde Schiff base of S-(4-methyl­benz­yl) di­thio­carbazate: crystal structure, Hirshfeld surface analysis and computational study

The title di­thio­carbazate ester (I), C18H18N2S2 [systematic name: (E)-4-methyl­benzyl 2-[(E)-3-phenyl­allyl­idene]hydrazinecarbodi­thio­ate, comprises an almost planar central CN2S2 residue [r.m.s. deviation = 0.0131 Å]. The methyl­ene(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 mol­ecule approximates mirror symmetry with the 4-tolyl group bis­ected by the plane. The configuration about both double bonds in the N—N=C—C=C chain is E; the chain has an all trans conformation. In the crystal, eight-membered centrosymmetric thio­amide synthons, {⋯HNCS}2, are formed via N—H⋯S(thione) hydrogen bonds. Connections between the dimers via C—H⋯π inter­actions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an inter­action profile similar to that of a closely related analogue with an S-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connected via N—H⋯S hydrogen bonds is about 0.94 kcal mol−1 more stable than that in (I).