[Journal logo]

Volume 65 
Part 7 
Page o1528  
July 2009  

Received 24 May 2009
Accepted 3 June 2009
Online 10 June 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.043
wR = 0.091
Data-to-parameter ratio = 14.7
Details
Open access

2,2',7,7'-Tetrabromo-9,9'-spirobifluorene toluene hemisolvate

aDepartment of Traditional Chinese Pharmacology, Shanxi University of Traditional Chinese Medicine, Taiyuan 030024, People's Republic of China, and bDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
Correspondence e-mail: ruitaozhu@126.com

There are two independent molecules and one toluene solvent molecule in the asymmetric unit of the title compound, C25H12Br4·0.5C7H8. The dihedral angles between the fluorene ring systems are 85.30 (6) and 84.95 (6)° in the two molecules. The disortions in angles from the ideal sp3-hybridization geometry around the tetrahedral C atoms are due to the strain imposed by the central five-membered ring and steric effects.

Related literature

For applications of spirobifluorene compounds, see: Hagen et al. (1997[Hagen, J., Schaffrach, W., Otschik, P., Fink, R., Bacher, A., Schmidt, H.-W. & Haarer, D. (1997). Synth. Met. 89, 215-220.]); Pudzich et al. (2006[Pudzich, R., Fuhrmann-Lieker, T. & Salbeck, J. (2006). Adv. Polym. Sci. 199, 83-142.]); Salbeck et al. (1997[Salbeck, J., Yu, N., Bauer, J., Weissortel, F. & Bestgen, H. (1997). Synth. Met. 91, 209-215.]); Iour et al. (1990[Iour, J. M., Wu, R. L. & Schumn, J. S. (1990). J. Am. Chem. Soc. 112, 5662-5663.]). For details of the synthesis, see: Marsitzky & Carter (2001[Marsitzky, D. & Carter, K. R. (2001). Polym. Prepr. 42, 450-451.]).

[Scheme 1]

Experimental

Crystal data
  • C25H12Br4·0.5C7H8

  • Mr = 678.06

  • Monoclinic, P 21 /c

  • a = 14.6593 (18) Å

  • b = 29.549 (4) Å

  • c = 11.3753 (14) Å

  • [beta] = 96.878 (2)°

  • V = 4891.9 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 6.60 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.15 mm

Data collection
  • Bruker SMART-CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.189, Tmax = 0.438 (expected range = 0.161-0.372)

  • 20291 measured reflections

  • 8616 independent reflections

  • 5479 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.091

  • S = 1.01

  • 8616 reflections

  • 586 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Selected bond angles (°)

C19-C9-C8 112.9 (3)
C19-C9-C21 101.0 (4)
C8-C9-C21 116.8 (4)
C19-C9-C6 113.4 (4)
C8-C9-C6 101.6 (3)
C21-C9-C6 111.6 (3)
C31-C34-C33 100.9 (4)
C31-C34-C46 114.2 (4)
C33-C34-C46 116.9 (4)
C31-C34-C44 113.7 (4)
C33-C34-C44 110.2 (4)
C46-C34-C44 101.5 (4)

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2831 ).


Acknowledgements

The authors thank Professors Bo Liu and Jianping Guo for supporting this work.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Marsitzky, D. & Carter, K. R. (2001). Polym. Prepr. 42, 450-451.  [ChemPort]
Hagen, J., Schaffrach, W., Otschik, P., Fink, R., Bacher, A., Schmidt, H.-W. & Haarer, D. (1997). Synth. Met. 89, 215-220.  [CrossRef] [ChemPort] [ISI]
Iour, J. M., Wu, R. L. & Schumn, J. S. (1990). J. Am. Chem. Soc. 112, 5662-5663.
Pudzich, R., Fuhrmann-Lieker, T. & Salbeck, J. (2006). Adv. Polym. Sci. 199, 83-142.  [CrossRef] [ChemPort]
Salbeck, J., Yu, N., Bauer, J., Weissortel, F. & Bestgen, H. (1997). Synth. Met. 91, 209-215.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2009). E65, o1528  [ doi:10.1107/S1600536809021072 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.