A monoclinic polymorph of N-ethoxycarbonyl-N′-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea

Abstract

The title compound, C12H13N5O2S {systematic name: ethyl N-[N-(3-phenyl-1H-1,2,4-triazol-5-yl)carbamothioyl]carbamate}, is a monoclinic polymorph (space group P21/c) which crystallizes with three similar independent molecules in the asymmetric unit. The triazole ring makes dihedral angles of 6.6 (2), 8.4 (2) and 10.6 (2)° with the phenyl ring in the three independent molecules. The structure was previously reported [Dolzhenko et al. (2010a). Acta Cryst., E46, o425] as a triclinic polymorph crystallizing in space group Poverline{1}. Molecules in both polymorphs possess two S(6) rings generated by intramolecular N—H...S and N—H...O hydrogen bonds, resulting in similar molecular geometries. However, the two polymorphs differ in the crystal packing. In contrast to the dimers of the triclinic polymorph, molecules of the monoclinic polymorph are connected by intermolecular N—H...S and N—H...N hydrogen bonds, forming pseudosymmetric trimers arranged in sheets parallel to (302).