4-[(1E)-({[(Benzyl­sulfan­yl)methane­thio­yl]amino}­imino)­meth­yl]benzene-1,3-diol chloro­form hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

The title hydrazine carbodi­thio­ate chloro­form hemisolvate, 2C15H14N2O2S2·CHCl3, comprises two independent hydrazine carbodi­thio­ate mol­ecules, A and B, and a chloro­form mol­ecule; the latter is statistically disordered about its mol­ecular threefold axis. The common features of the organic mol­ecules include an almost planar, central CN2S2 chromophore [r.m.s. deviation = 0.0203 Å (A) and 0.0080 Å (B)], an E configuration about the imine bond and an intra­molecular hydroxyl-O—H⋯N(imine) hydrogen bond. The major conformational difference between the mol­ecules is seen in the relative dispositions of the phenyl rings as indicated by the values of the dihedral angles between the central plane and phenyl ring of 71.21 (6)° (A) and 54.73 (7)° (B). Finally, a difference is seen in the disposition of the outer hydroxyl-H atoms, having opposite relative orientations. In the calculated gas-phase structure, the entire mol­ecule is planar with the exception of the perpendicular phenyl ring. In the mol­ecular packing, the A and B mol­ecules assemble into a two-mol­ecule aggregate via N—H⋯S hydrogen bonds and eight-membered {⋯HNCS}2 synthons. The dimeric assemblies are connected into supra­molecular chains via hydroxyl-O—H⋯O(hydrox­yl) hydrogen bonds and these are linked into a double-chain through hy­droxy-O—H⋯π(phen­yl) inter­actions. The double-chains are connected into a three-dimensional architecture through phenyl-C—H⋯O(hydrox­yl) and phenyl-C—H⋯π(phen­yl) inter­actions. The overall assembly defines columns along the a-axis direction in which reside the chloro­form mol­ecules, which are stabilized by chloro­form–methine-C—H⋯S(thione) and phenyl-C—H⋯Cl contacts. The analysis of the calculated Hirshfeld surfaces, non-covalent inter­action plots and inter­action energies confirm the importance of the above-mentioned inter­actions, but also of cooperative, non-standard inter­actions such as π(benzene)⋯π(hydrogen-bond-mediated-ring) contacts.