5-(4-Fluorophenyl)-3-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothioamide

In the title compound, C20H19FN6S, 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 thiourea group is coplanar with the pyrazole ring [N—N—C—S torsion angle = −179.93 (11)°], which enables the formation of an intramolecular N—H⋯N hydrogen bond. In the crystal, inversion-related molecules associate via N—H⋯S hydrogen bonds and eight-membered {⋯HNCS}2 synthons feature in the crystal packing. These synthons are connected into supramolecular 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.

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 thiourea group is coplanar with the pyrazole ring [N-N-C-S torsion angle = À179.93 (11) ], which enables the formation of an intramolecular N-HÁ Á ÁN hydrogen bond. In the crystal, inversion-related molecules associate via N-HÁ Á ÁS hydrogen bonds and eight-membered {Á Á ÁHNCS} 2 synthons feature in the crystal packing. These synthons are connected into supramolecular chains along the a axis via N-HÁ Á ÁF hydrogen bonds, and the chains are consolidated into layers in the ab plane via C-HÁ Á ÁS and C-HÁ Á ÁF contacts.
The pyrazole ring in (I), Fig. 1, adopts an envelope conformation (r.m.s. deviation = 0.138 Å) with the methine-C2 atom being the flap atom. The dihedral angle between the least-squares plane through this ring and the adjacent triazole ring is 7.59 (9)°. The benzene ring connected to the triazole ring is twisted out of its plane, forming a dihedral angle of 74.79 (9)°. The N3-N2-C1-S1 torsion angle of -179.93 (11)° indicates that the thiourea moiety is coplanar with the pyrazole ring. This arrangement coupled with the orientation of the amino group towards the ring enables the formation of an intramolecular N-H···N hydrogen bond (Table 1).
In the crystal, centrosymmetrically related molecules associate via N-H···S hydrogen bonds and eight-membered {···HNCS} 2 synthons feature in the crystal packing (Table 1). These are connected into supramolecular chains along the a axis via N-H···F hydrogen bonds ( Fig. 2 and Table 1). Chains are connected into layers in the ab plane via C-H···S and C-H···F contacts (Table 1). Layers inter-digitate along the c axis with no specific interactions between them (Fig. 3).

Experimental
The title compound was prepared according to the reported method (Abdel-Wahab et al., 2012a). Crystals were obtained from its DMF solution by slow evaporation at room temperature.

Refinement
C-bound H atoms were placed in calculated positions [C-H = 0.95 to 1.00 Å, U iso (H) = 1.2U eq (C) or 1.5U eq (C) for methyl H atoms] and were included in the refinement in the riding model approximation. The N-bound H atoms were freely refined.  The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.   Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.