4-[(E)-(4-Fluorobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione

Abstract

In the asymmetric unit of the title compound, C10H9FN4S, there are two independent mol­ecules in which the dihedral angles between the 1,2,4-triazole and benzene rings are 36.85 (10) and 7.81 (10)°. In the crystal, N—H⋯S inter­actions link pairs of independent mol­ecules into dimers. There are also π–π inter­actions between the triazole and benzene rings of inversion-related pairs of the more planar mol­ecule [centroid–centroid distance = 3.6430 (13) Å].

3-Methyl-4-{(E)-[4-(methylsulfanyl)benzylidene]amino}-1H-1,2,4-triazole-5(4H)-thione

“…In the title compound ( Fig. 1), the bond lengths and angles have values in the normal ranges (Allen et al, 1987) and are comparable with closely related structures (Devarajegowda et al, 2012;Fun et al, 2008;Wang et al, 2008). The dihedral angle between the triazole ring (N1/N2/C3/N4/C5) and the benzene ring (C9-C14) is 21.31 5…”

“…For biological applications of sulfur-and nitrogen-containing compounds, see: Wei et al (1981Wei et al ( , 1982; Thieme et al (1973a,b); Dornow et al (1964); Barrera et al (1985); Malik et al, (2011). For related structures, see: Devarajegowda et al (2012); Fun et al (2008); Wang et al (2008). For standard bond-length data, see: Allen et al (1987).…”

The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione

“…Compounds (IV) (Devarajegowda et al, 2012) and (V) (Sarojini, Manjula, Kaur et al, 2014) both crystallize in the triclinic space group P1, but they are not isostructural, as they crystallize with Z 0 values of 2 and 1, respectively. However, their supramolecular assembly is rather similar: in the structure of compound (IV), two independent N-HÁ Á ÁS hydrogen bonds link the two molecules of the selected asymmetric unit into a cyclic dimeric aggregate, while in compound (V) inversion-related pairs of molecules are linked by N-HÁ Á ÁS hydrogen bonds to form a cyclic centrosymmetric R 2 2 (8) dimer, analogous to those found in both polymorphs of compound (III Part of the crystal structure of the monoclinic polymorph of compound (III) showing the formation of a hydrogen-bonded R 2 2 (8) dimer.…”