3-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-N-phenyl-5-[4-(piperidin-1-yl)phenyl]-4,5-dihydro-1H-pyrazole-1-carbothioamide dimethylformamide hemisolvate

The essentially planar pyrazole ring (r.m.s. deviation = 0.013 Å) in the title hemisolvate, C31H33N7S·0.5C3H7NO, is almost coplanar with the pendant thiourea residue [N—N—C—S torsion angle = −173.2 (4)°] and slightly twisted with respect to the triazole ring [dihedral angle = 7.7 (3)°]. An intramolecular thiourea–pyrazole N—H⋯N hydrogen bond, via an S(5) loop, is formed. Supramolecular chains along the c axis are formed in the crystal via piperidine–triazole C—H⋯N interactions. These are bridged into loosely associated double chains via C—H⋯O interactions involving the disordered (over two positions) dimethylformamide solvent molecules. The thiourea-bound phenyl ring is also disordered over two positions of equal occupancy.

The essentially planar pyrazole ring (r.m.s. deviation = 0.013 Å ) in the title hemisolvate, C 31 H 33 N 7 SÁ0.5C 3 H 7 NO, is almost coplanar with the pendant thiourea residue [N-N-C-S torsion angle = À173.2 (4) ] and slightly twisted with respect to the triazole ring [dihedral angle = 7.7 (3) ]. An intramolecular thiourea-pyrazole N-HÁ Á ÁN hydrogen bond, via an S(5) loop, is formed. Supramolecular chains along the c axis are formed in the crystal via piperidine-triazole C-HÁ Á ÁN interactions. These are bridged into loosely associated double chains via C-HÁ Á ÁO interactions involving the disordered (over two positions) dimethylformamide solvent molecules. The thiourea-bound phenyl ring is also disordered over two positions of equal occupancy.
In (I), Fig. 1, the pyrazole ring is planar with a r.m.s. deviation = 0.013 Å; the maximum deviation is 0.005 (6) Å for the N2 atom. The thiourea group is close to co-planar with the ring [the N3-N2-C7-S1 torsion angle = -173.2 (4)°] and the connected triazole ring is slightly twisted out of the plane [dihedral angle = 7.7 (3)°]. There is a significant twist between the triazole and attached benzene rings with the dihedral angle being 49.4 (3)°. The conformation of the piperidinyl ring is close to a chair. The thiourea-N-H atom is orientated towards the pyrazole-N3 atom and forms a hydrogen bond via an S(5) loop, Table 1.
In the crystal packing, connections between molecules are of the type piperidinyl-C-H···N(triazole), Table 1, leading to the formation of a supramolecular chain along the c axis. Two chains are connected by the (disordered) dimethylformamide molecules via methyl-C13-H···O1 interactions into a loosely associated double chain, Fig. 2 and Table 1.

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
The H-atoms were placed in calculated positions [N-H = 0.88 Å; C-H = 0.95 to 0.98 Å, U iso (H) = 1.2-1.5U eq (N,C)] and were included in the refinement in the riding model approximation.
The phenyl ring is disordered over two positions in an assumed 1:1 ratio; the ring was refined as a rigid hexagon with 1.39 Å sides. The displacement factors of the primed atoms were set to those of the unprimed ones.
The DMF molecule is disordered over a twofold rotation axis. The C-O distance was restrained to 1.25±0.01 Å and the N-C carbonyl distance to 1.35±0.01 Å; the other two N-C distances were restrained to 1.45±0.01 Å. Additionally, the 1,3related distances were also restrained. The anisotropic displacement parameters were tightly restrained to be nearly isotropic.
The absolute structure could not be refined despite the presence of a sulfur atom as the crystal is a racemic twin; 1153 Friedel pairs were merged. The maximum and minimum residual electron density peaks of 0.71 and 1.06 e Å -3 , respectively, were located 0.71 Å and 0.82 Å, respectively, from the S1 atom.

Figure 1
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.