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, mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via C-H⋯π inter-actions, forming chains along [1-10]. The chains are linked via π-π inter-actions involving inversion-related triazole rings [centroid-centroid distance = 3.4340 (13) Å], forming layers parallel to the ab plane.

Highlights

  • The title compound, C23H22FN5S, exists in a trans conformation with respect to the methene C C and the acyclic N C bonds

  • The synthesis and functionalization of indoles has been a major area of focus for researchers for several decades

  • Indoles are of great importance in view of their natural occurrence as a prominent sub-structure of a large number of alkaloids (Somei & Yamada, 2003; Hibino & Choshi, 2002)

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Summary

Chemical context

The synthesis and functionalization of indoles has been a major area of focus for researchers for several decades. Wide-ranging biological activities (Gribble, 1995). They constitute an important moiety of various drugs. 1,2,4-triazoles are an important class of heterocyclic compounds which are well known for their potential antimicrobial properties. The proper design of indoles and triazoles can be used to prepare Schiff bases. The wide spectrum of biological applications of 1,2,4-triazoles prompted us to synthesize Schiff bases derived from triazole and indole derivatives. CH N is thought to be the main reason for the biological properties of Schiff bases. We have reported a number of metal complexes of Schiff bases, recently, which possess very good antimicrobial properties (Kulkarni et al, 2009a,b, 2011)

Structural commentary
Supramolecular features
Synthesis and crystallization
Refinement
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