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 [R 2 2(6) graph-set motif] and the second is an N—H⋯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.