(E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate

Abstract

The title 1,2,4-triazole compound, C13H11N5OS·C3H7NO, crystallizes as a 1:1 dimethylformamide (DMF) solvate. The main molecule exists in a trans configuration with respect to the acyclic C=N bond. An intramolecular C—H...S hydrogen bond generates an S(6) ring motif. In the synthesis, a proton is transferred from the O atom of a hydroxy group to the quinoline group N atom. The essentially planar triazole ring and quinoline ring system [maximum deviations of 0.001 (2) and 0.013 (2) Å, respectively] form a dihedral angle of 5.86 (9)°. In the crystal structure, molecules of (E)-4-[(2-hydroxy-3-quinolyl)methyleneamino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione are linked into R22(8) centrosymmteric dimers via N—H...O hydrogen bonds. These dimers are further linked into an extended three-dimensional structure by the DMF solvent molecules via intermolecular N—H...O and C—H...O hydrogen bonds. The crystal structure is consolidated by two different intermolecular π–π interactions [centroid–centroid distances = 3.6593 (12) and 3.6892 (12) Å].