1,3-Diphenyl-8-trifluoromethyl-1H-pyrazolo[3,4-b]quinoline

The 1H-pyrazolo[3,4-b]quinoline (PQ) core of the title molecule, C23H14F3N3, is aromatic and essentially planar (r.m.s. deviation = 0.015 Å) and the two phenyl substituents at positions 1 and 3 are twisted relative to this fragment by 29.74 (7) and 25.63 (7)°, respectively. In the crystal, molecules are arranged along the b axis into stacks via π–π interactions, with an interplanar distance of the PQ core of 3.489 (4) Å.

The 1H-pyrazolo [3,4-b]quinoline (PQ) core of the title molecule, C 23 H 14 F 3 N 3 , is aromatic and essentially planar (r.m.s. deviation = 0.015 Å ) and the two phenyl substituents at positions 1 and 3 are twisted relative to this fragment by 29.74 (7) and 25.63 (7) , respectively. In the crystal, molecules are arranged along the b axis into stacks viainteractions, with an interplanar distance of the PQ core of 3.489 (4) Å .
The product was purified by column chromatography (SilicaGel 60, toluene/petroleum ether 1:1 as the eluent) followed by preparative TLC (SilicaGel 60, 2 mm, toluene/petroleum ether 1:1 as the eluent) to give 50 mg (2.6% yield -the low yield is caused by strong induction electron-withdrawing effect of the trifluoromethyl group in ortho-position to the amine group) of yellow crystalline solid, mp. suitable for X-ray diffraction were grown by slow evaporation from toluene solution.

Refinement
As the structure contains only C, H, N and F atoms Friedel pairs were merged and absolute structure was not determined.
H atoms were included into refinement in geometrically calculated positions, with C-H = 0.93 Å, and U iso (H) = 1.2U eq ( C) for the aromatic CH groups, and constrained as a part of a riding model.  Projection of the unit-cell contents along [100] showing layered structure. The unit cell origin is at the lower right-hand corner of the cell with a axis pointed down. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.16 e Å −3 Δρ min = −0.18 e Å −3

Special details
Geometry. All e.s.d.'s 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. 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.