Halogen, chalcogen, and hydrogen bonding in organoiodine cocrystals of heterocyclic thio­nes: imidazolidine-2-thione, 2-mercaptobenzimidazole, 2-mercapto-5-methyl­benzimidazole, 2-mercaptobenzoxazole, and 2-mercaptobenzo­thia­zole

Through the combination of heterocyclic thio­nes with variation in the identity of the heterocyclic elements, namely, imidazolidine-2-thione, 2-mercaptobenzimid­azole, 2-mercapto-5-methyl­benz­imidazole, 2-mercaptobenzoxazole, and 2-mer­captobenzo­thia­zole with the common halogen-bond donors 1,2-, 1,3-, and 1,4-di­iodo­tetra­fluoro­benzene, 1,3,5-tri­fluoro­tri­iodo­benzene, and tetra­iodo­ethyl­ene, a series of 18 new crystalline structures were characterized. In most cases, N—H⋯S hydrogen bonding was observed, with these inter­actions in imidazole-con­taining structures typically resulting in two-dimensional motifs (i.e. ribbons). Lacking the second N—H group, the thia­zole and oxazole hydrogen bonding resulted in only dimeric pairs. C—I⋯S and C—I⋯I halogen bonding, as well as C=S⋯I chalcogen bonding, served to consolidate the packing by linking the hydrogen-bonding ribbons or dimeric pairs.