Crystal structure of 4-({(1E,2E)-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]allylidene}amino)-5-methyl-1H-1,2,4-triazole-5(4H)-thione

Abstract

The title compound, C23H22FN5S, exists in a trans conformation with respect to the methene C=C and the acyclic N=C bonds. The 1,2,4-triazole-5(4H)-thione ring makes dihedral angles of 88.66 (9) and 84.51 (10)°, respectively, with the indole and benzene rings. In the crystal, molecules are linked by pairs of N—H...S hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked via C—H...π interactions, forming chains along [1-10]. The chains are linked via π—π interactions involving inversion-related triazole rings [centroid–centroid distance = 3.4340 (13) Å], forming layers parallel to the ab plane.

Keywords

• crystal structure
• 1,2,4-triazole-5(4H)-thione
• indole
• Schiff base
• N—H...S hydrogen bonds
• C—H...π and π–π interactions