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

Guo, A.; Zhu, R.

doi:10.1107/S1600536809021072

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 (C-C) = 0.007 Å
R = 0.043
wR = 0.091
Data-to-parameter ratio = 14.7
Details

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

Ailing Guo ^a and Ruitao Zhu ^b ^*

^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); Salbeck et al. (1997); Iour et al. (1990). For details of the synthesis, see: Marsitzky & Carter (2001).

Experimental

Crystal data

C₂₅H₁₂Br₄·0.5C₇H₈
M_r = 678.06
Monoclinic, P 2₁ /c
a = 14.6593 (18) Å
b = 29.549 (4) Å
c = 11.3753 (14) Å
= 96.878 (2)°
V = 4891.9 (10) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.189, T_max = 0.438 (expected range = 0.161-0.372)
20291 measured reflections
8616 independent reflections
5479 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.091
S = 1.01
8616 reflections
586 parameters
H-atom parameters constrained
_max = 0.56 e Å^-3
_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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
Hagen, J., Schaffrach, W., Otschik, P., Fink, R., Bacher, A., Schmidt, H.-W. & Haarer, D. (1997). Synth. Met. 89, 215-220.
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.
Salbeck, J., Yu, N., Bauer, J., Weissortel, F. & Bestgen, H. (1997). Synth. Met. 91, 209-215.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds