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Volume 66 
Part 3 
Page o575  
March 2010  

Received 4 January 2010
Accepted 4 February 2010
Online 10 February 2010

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Key indicators
Single-crystal X-ray study
T = 293 KP 98.6 kPa
Mean [sigma](C-C) = 0.004 Å
R = 0.064
wR = 0.137
Data-to-parameter ratio = 16.2
Details
Open access

6-Fluoro-1,3,4-triphenyl-1H-pyrazolo[3,4-b]quinoline benzene hemisolvate

Pawel Szlachcica* and Katarzyna Stadnickab

aDepartment of Chemistry and Physics, Agricultural University, 30-149 Kraków, Poland, and bFaculty of Chemistry, Jagiellonian University, 30-060 Kraków, Poland
Correspondence e-mail: pszlachcic@ar.krakow.pl

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 [pi]...[pi] 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.

Related literature

For the synthesis of 1H-pyrazolo[3,4-b]quinoline derivatives, see: Chaczatrian et al. (2003[Chaczatrian, K., Chaczatrian, G., Danel, A. & Tomasik, P. (2003). Pol. J. Chem. 77, 1141-1147.], 2007[Chaczatrian, K., Chaczatrian, G., Danel, A. & Tomasik, P. (2007). Polish Patent PL 195700 B1.]). For their photophysical properties, see: Gondek et al. (2006[Gondek, E., Kityk, I. V., Sanetra, J., Szlachcic, P., Armatys, P., Wisla, A. & Danel, A. (2006). Opt. Laser Technol. 38, 487-492.]). 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[Tao, Y. T., Balasubramaniam, E., Danel, A., Jarosz, B. & Tomasik, P. (2001). Chem. Mater. 13, 1207-1212.]). For the effect of substituents on aromatic ring geometry, see: Domenicano et al. (1975[Domenicano, A., Vaciago, A. & Coulson, C. A. (1975). Acta Cryst. B31, 221-234.]).

[Scheme 1]

Experimental

Crystal data

  • C28H18FN3·0.5C6H6

  • Mr = 454.51

  • Monoclinic, P 21 /c

  • a = 13.2941 (4) Å

  • b = 9.7419 (3) Å

  • c = 20.7608 (5) Å

  • [beta] = 118.559 (2)°

  • V = 2361.58 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.40 × 0.25 × 0.03 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (HKL DENZO and SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.968, Tmax = 0.998

  • 8615 measured reflections

  • 5135 independent reflections

  • 2974 reflections with I > 2[sigma](I)

  • Rint = 0.051
Refinement

  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.137

  • S = 1.06

  • 5135 reflections

  • 317 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: HKL DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2254 ).

Acknowledgements

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.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Chaczatrian, K., Chaczatrian, G., Danel, A. & Tomasik, P. (2003). Pol. J. Chem. 77, 1141-1147.  [ChemPort]
Chaczatrian, K., Chaczatrian, G., Danel, A. & Tomasik, P. (2007). Polish Patent PL 195700 B1.
Domenicano, A., Vaciago, A. & Coulson, C. A. (1975). Acta Cryst. B31, 221-234.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gondek, E., Kityk, I. V., Sanetra, J., Szlachcic, P., Armatys, P., Wisla, A. & Danel, A. (2006). Opt. Laser Technol. 38, 487-492.  [CrossRef] [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tao, Y. T., Balasubramaniam, E., Danel, A., Jarosz, B. & Tomasik, P. (2001). Chem. Mater. 13, 1207-1212.  [ISI] [CrossRef] [ChemPort]

Acta Cryst (2010). E66, o575  [ doi:10.1107/S1600536810004496 ]

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