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The common features of the organic molecules include an almost planar, central CN<jats:sub>2<\/jats:sub>S<jats:sub>2<\/jats:sub> chromophore [r.m.s. deviation = 0.0203\u2005\u00c5 (<jats:italic>A<\/jats:italic>) and 0.0080\u2005\u00c5 (<jats:italic>B<\/jats:italic>)], an <jats:italic>E<\/jats:italic> configuration about the imine bond and an intramolecular hydroxyl-O\u2014H...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\u2005(6)\u00b0 (<jats:italic>A<\/jats:italic>) and 54.73\u2005(7)\u00b0 (<jats:italic>B<\/jats:italic>). 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 <jats:italic>A<\/jats:italic> and <jats:italic>B<\/jats:italic> molecules assemble into a two-molecule aggregate <jats:italic>via<\/jats:italic> N\u2014H...S hydrogen bonds and eight-membered {...HNCS}<jats:sub>2<\/jats:sub> synthons. The dimeric assemblies are connected into supramolecular chains <jats:italic>via<\/jats:italic> hydroxyl-O\u2014H...O(hydroxyl) hydrogen bonds and these are linked into a double-chain through hydroxy-O\u2014H...\u03c0(phenyl) interactions. The double-chains are connected into a three-dimensional architecture through phenyl-C\u2014H...O(hydroxyl) and phenyl-C\u2014H...\u03c0(phenyl) interactions. The overall assembly defines columns along the <jats:italic>a<\/jats:italic>-axis direction in which reside the chloroform molecules, which are stabilized by chloroform\u2013methine-C\u2014H...S(thione) and phenyl-C\u2014H...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 \u03c0(benzene)...\u03c0(hydrogen-bond-mediated-ring) contacts.<\/jats:p>","DOI":"10.1107\/s2056989020007070","type":"journal-article","created":{"date-parts":[[2020,6,2]],"date-time":"2020-06-02T09:38:23Z","timestamp":1591090703000},"page":"990-997","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["4-[(1<i>E<\/i>)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study"],"prefix":"10.1107","volume":"76","author":[{"given":"Nadia Liyana","family":"Khairuanuar","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karen A.","family":"Crouse","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5130-8011","authenticated-orcid":true,"given":"Huey Chong","family":"Kwong","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5343-3382","authenticated-orcid":true,"given":"Sang Loon","family":"Tan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1401-1520","authenticated-orcid":true,"given":"Edward R. 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