5-(4-Fluoro-phen-yl)-3-[5-methyl-1-(4-methyl-phen-yl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothio-amide

Abstract

In the title compound, C(20)H(19)FN(6)S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angle between the least-squares plane through the pyrazole and triazole rings is 7.59 (9)°, and the triazole and attached benzene ring form a dihedral angle of 74.79 (9)°. The thio-urea group is coplanar with the pyrazole ring [N-N-C-S torsion angle = -179.93 (11)°], which enables the formation of an intra-molecular N-H⋯N hydrogen bond. In the crystal, inversion-related mol-ecules associate via N-H⋯S hydrogen bonds and eight-membered {⋯HNCS}(2) synthons feature in the crystal packing. These synthons are connected into supra-molecular chains along the a axis via N-H⋯F hydrogen bonds, and the chains are consolidated into layers in the ab plane via C-H⋯S and C-H⋯F contacts.

Fig. 1.

The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.

Fig. 2.

A view of a supramolecular chain along the a axis in (I). The N—H···S and N—H···F hydrogen bonds are shown as blue and orange dashed lines, respectively.

Fig. 3.

A view in projection down the b axis of the unit-cell contents for (I) highlighting the inter-digitation of layers along the c axis. The N—H···S, N—H···F, C—H···S and C—H···F interactions are shown as blue, orange, purple and brown dashed lines, respectively.