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

In the title compound, C26H23FN6S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The thiourea group is close to being coplanar with the pyrazole N atoms [N—N—C—S torsion angle = 176.78 (15)°], which allows for an intramolecular N—H⋯N hydrogen bond; the connected triazole ring is nearly coplanar with this ring [N—C—C—N = −172.65 (19)°]. There is a significant twist between the pyrazole ring and attached fluorobenzene ring [N—C—C—C = −18.8 (3)°] and a greater twist between triazole and attached tolyl ring [dihedral angle = 58.25 (14)°]. In the crystal, supramolecular chains aligned along [40,10] are consolidated by π–π interactions between the triazole and phenyl rings [centroid–centroid distance = 3.7053 (13) Å].

In the title compound, C 26 H 23 FN 6 S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The thiourea group is close to being coplanar with the pyrazole N atoms [N-N-C-S torsion angle = 176.78 (15) ], which allows for an intramolecular N-HÁ Á ÁN hydrogen bond; the connected triazole ring is nearly coplanar with this ring [N-C-C-N = À172. 65 (19) ]. There is a significant twist between the pyrazole ring and attached fluorobenzene ring [N-C-C-C = À18.8 (3) ] and a greater twist between triazole and attached tolyl ring [dihedral angle = 58.25 (14) ]. In the crystal, supramolecular chains aligned along [40,10] are consolidated byinteractions between the triazole and phenyl rings [centroid-centroid distance = 3.7053 (13) Å ].   Table 1 Hydrogen-bond geometry (Å , ).

Comment
In connection with studies into the biological studies on related pyrazolines (Abdel-Wahab, Abdel-Latif et al., 2012), the title compound, (I), was investigated.
In (I), Fig. 1, the pyrazole ring has an envelope conformation with the methine-C8 atom being the flap atom. The thiourea group is close to co-planar with the N atoms of this ring [the N3-N2-C7-S1 torsion angle = 176.78 (15)°], which allows for an intramolecular N1-H···N3 hydrogen bond, Table 1, and the connected triazole ring is slightly

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

Refinement
Carbon-bound H-atoms were placed in calculated positions (C-H = 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U iso (H) = 1.2-1.5U equiv (C). The nitrogen-bound H-atom was refined freely.     A view of the crystal packing in projection down the a axis. The π-π interactions are shown as purple dashed lines.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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.