Crystal structure of a 1,1,2,2-tetrachloroethane-solvated 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.

Keywords

• crystal structure
• Schiff base
• hydrogen bonding
• tautomerism