(2Z)-2-(5-Fluoro-1-methyl-2-oxoindolin-3-ylidene)-N-(3-fluorophenyl)hydrazine-1-carbothioamide

Abstract

In the title compound, C16H12F2N4OS, the whole molecule is essentially planar (r.m.s deviation = 0.003 Å), with only the H atoms of the methyl group lying out of the molecular plane. A planar indole fused-ring system (r.m.s deviation = 0.004 Å) is linked through a hydrazine–carbothioamide bridge to a fluorobenzene ring, with the indole ring system and inclined to the fluorobenzene ring by 4.26 (14)°. The planarity of the molecule is strengthened by three intramolecular N—H...N, N—H...O and C—H...S hydrogen bonds that generateS(5),S(6) andS(6) ring motifs, respectively. In the crystal, π–π stacking interactions combine with C—H...·F hydrogen bonds to link the molecules into layers parallel to the (10-1) plane.