Received 4 January 2010
In the title compound, C28H18FN3·0.5C6H6, the 1H-pyrazolo[3,4-b]quinoline core is almost planar (r.m.s = 0.0371 Å, maximum deviation = 0.0571 Å) and aromatic. The solvent benzene molecules are located around inversion centres. In the crystal, molecules related by centres of symmetry form dimers, with distances of 3.932 (3) Å between best planes through the fused core due to stacking. The phenyl substituents at positions 1, 3 and 4, are twisted away from the core, making dihedral angles of 29.66 (7), 44.59 (7) and 67.94 (6)°, respectively.
For the synthesis of 1H-pyrazolo[3,4-b]quinoline derivatives, see: Chaczatrian et al. (2003, 2007). For their photophysical properties, see: Gondek et al. (2006). For the use of a fluorine derivative of 1H-pyrazolo[3,4-b]quinoline in organic light-emitting diode preparation, see: Tao et al. (2001). For the effect of substituents on aromatic ring geometry, see: Domenicano et al. (1975).
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2254 ).
The authors are grateful to the Ministry of Science and Higher Education, Poland, for financial support of this work through grant No. N N204 216734.
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