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

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 center dot center dot center dot S = C between the endocyclic N-bound H atom and the thioureido S atom, and N-H center dot center dot center dot 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)degrees. 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 [R-2(2)(6) graph-set motif] and the second is an N-H center dot center dot center dot S C interaction between the imide H atoms and the thiocarbonyl S atoms [R-2(2)(8) graph-set motif]. Together, they form a network parallel to the (111) plane.