N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea

Abstract

The title compound, [systematic name: ethyl ({[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]amino}carbonothioyl)carbamate], C13H16N5O2S, exists in the 3-aryl-5-thioureido-1H-1,2,4-triazole tautomeric form. The molecular structure is stabilized by intramolecular hydrogen bonding (N—H...S=C between the endocyclic N-bound H atom and the thioureido S atom, and N—H...O=C within the ethoxycarbonylthiourea unit), both arranged in an S(6) graph-set motif. The mean planes of the phenyl and 1,2,4-triazole rings make a dihedral angle of 6.59 (10)°. In the crystal structure, the molecules form two types of centrosymmetric dimers connected by intermolecular hydrogen bonds; in the first, the N—NH triazole sides of two molecules are connected [R22(6) graph-set motif] and the second is an N—H...S=C interaction between the imide H atoms and the thiocarbonyl S atoms [R22(8) graph-set motif]. Together, they form a network parallel to the (111) plane.