Crystal structure of a 1,1,2,2-tetrachloroethanesolvated hydrazinecarbothioamide compound

Abstract

The title compound, [(1-{4-[2-(2,4-dihydroxyphenyl)diazen-1-yl]phenyl}ethylidene)amino]thiourea, 1,1,2,2-tetrachloroethane monosolvate, C15H15N5O2S·C2H2Cl4, was prepared from 4-(4-acetylphenyldiazendiyl)resorcinol and thiosemicarbazide and recrystallized from mixed solvents of tetrachloroethane and n-hexane. 1H NMR and X-ray diffraction data are in support of the thione tautomeric form. The X-ray analysis shows the molecule crystallizes as a zwitterion, with proton transfer from the nominal phenol to the azide group; the N-N bond length is 1.291(5)Å, and an intramolecular N-H⋯O hydrogen bond is formed. In the crystal, N-H⋯O, N-H⋯N and O-H⋯S hydrogen bonds connect the molecules into a three-dimensional network. The tetrachloroethane solvent molecules are linked to this network through weak C-H⋯O linkages.