4-{1-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole

In the title compound, C28H22BrFN6S, the central pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angles between the least-squares plane through this ring and the adjacent thiazole [18.81 (15)°] and triazole [1.83 (16)°] rings indicate a twist in the molecule. A further twist is evident by the dihedral angle of 64.48 (16)° between the triazole ring and the attached benzene ring. In the crystal, C—H⋯N, C—H⋯F, C—H⋯π and π–π interactions [occurring between the thiazole and triazole rings, centroid–centroid distance = 3.571 (2) Å] link molecules into a three-dimensional architecture. The sample studied was a non-merohedral twin; the minor twin component refined to 47.16 (7)%.

In the title compound, C 28 H 22 BrFN 6 S, the central pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angles between the leastsquares plane through this ring and the adjacent thiazole [18.81 (15) ] and triazole [1.83 (16) ] rings indicate a twist in the molecule. A further twist is evident by the dihedral angle of 64.48 (16) between the triazole ring and the attached benzene ring. In the crystal, C-HÁ Á ÁN, C-HÁ Á ÁF, C-HÁ Á Á andinteractions [occurring between the thiazole and triazole rings, centroid-centroid distance = 3.571 (2) Å ] link molecules into a three-dimensional architecture. The sample studied was a non-merohedral twin; the minor twin component refined to 47.16 (7)%.

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 [N-H = 0.88 Å and C-H = 0.95 to 1.00 Å, U iso (H) = 1.2U eq (N,C) or = 1.5U eq (C-methyl)] and were included in the refinement in the riding model approximation. The sample studied is a non-merohedral twin and a full sphere of reflections was measured. As it was not possible to separate the diffraction spots in two domains, the twin domains were separated using the TwinRotMat routine of PLATON (Spek, 2009). The minor twin component refined to 47.16 (7)%. Two reflections, i.e. (-11 -8 2) and (0 -2 4), were omitted owing to poor agreement. The maximum and minimum residual electron density peaks of 1.44 and 0.53 e Å -3 , respectively, were located 0.51 Å and 0.81 Å from the H13C and F9 atoms, respectively. structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figure 1
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.

Figure 2
A view in projection down the c axis of the unit-cell contents for (I). The C-H···N, C-H···F, C-H···π and π-π interactions are shown as blue, orange, purple and brown dashed lines, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq