2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-[(4-fluorophenyl)diazenyl]-4-methylthiazole

Pairs of molecules related by inversion symmetry are linked by intermolecular C—H⋯F contacts with R(8)2 2 geometry.

The molecule of the title compound, C 25 H 18 ClF 2 N 5 S, comprises almost coplanar fluorophenyl, methylthiazolyl, pyrazolyl and chlorophenyl rings with the second fluorophenyl ring almost perpendicular to this plane. One fluorophenyl group is disordered over two components of occupancy ratio 0.767 (10):0.233 (10) related by a 24.2 (8) twist. In the crystal, two molecules related by inversion symmetry are linked by a pair of C-HÁ Á ÁF contacts in an R(8) 2 2 geometry.

data reports
Rings A-D are close to coplanar with twist angles A/B, B/C and C/D of 4.76 (10) , 6.51 (11) and 10.46 (11) respectively. Ring E is almost perpendicular to A-D with a C/E twist angle of 72.66 (3) for the major component of E.
In the crystal structure, two molecules related by inversion symmetry are linked by a pair of C-HÁ Á ÁF contacts (Table 1, Fig. 2) with R(8) 2 2 geometry to form a dimer. The pyrazolyl and fluorophenyl rings of neighbouring molecules are almost parallel with a centroid-to-centroid distance of 3.6510 (13) Å .

Figure 2
A segment of the crystal structure showing intermolecular contacts for the major component of the disordered structure.

Figure 1
ORTEP representation of the title molecule showing 50% probability ellipsoids.
where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.14 e Å −3 Δρ min = −0.21 e Å −3 data reports data-2 IUCrData (2020). 5, x200700 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Non-hydrogen atoms were refined with anisotropic diaplacement parameters. All hydrogen atoms were placed in calculated positions and refined using a riding model. Difference Fourier maps showed that the methyl hydrogen atoms were disordered. The methyl group was therefore modelled as two components related by a 60° rotation about the C-C bond and the C-H bond distances were fixed at 0.96 Å, with displacement parameters 1.5 times Ueq(C). The hydrogen atoms were allowed to rotate freely and the occupancy ratio for the two components refined to 57 (3):43 (3)%. C-H distances for sp 2 hybridized groups were set to 0.93Å and their U iso (H) set to 1.2 times the U eq (C). Methine and methylene C-H bond distances were fixed at 0.98 Å and 0.97 Å with displacement parameters 1.2 times Ueq(C).