1-[N-Methyl-N-(Phenyl)amino]-3-(4-Methylphenyl)Thiourea

The title compound, 1-[N-methyl-N-(phenyl) amino]-3-(4-methylphenyl)thiourea (1), was synthesized by the reaction of 1-methyl-1-phenyl hydrazine and 4-tolyl isothiocyanate, and was characterized by spectroscopy (H-1 and C-13{H-1} NMR, IR, and UV), elemental analysis as well as by single crystal X-ray crystallography. In the solid state, the molecule exists as the thioamide tautomer and features an anti-disposition of the thioamide-N-H atoms; an intramolecular N-H center dot center dot center dot N hydrogen bond is noted. The molecular conformation resembles that of the letter L. In the molecular packing, thioamide-N1-H center dot center dot center dot S1(thione) hydrogen bonds lead to centrosymmetric eight-membered {center dot center dot center dot HNCS}(2) synthons. The dimers are assembled into a supramolecular layer in the bc-plane by phenyl- and methyl-C-H center dot center dot center dot p (phenyl) interactions.