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Volume 66 
Part 5 
Page o1034  
May 2010  

Received 23 March 2010
Accepted 31 March 2010
Online 10 April 2010

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.032
wR = 0.085
Data-to-parameter ratio = 12.3
Details
Open access

2,7-Dibromo-9,9-dimethyl-9H-fluorene

Xiao Chen,a Xinliang Fu,a Yongkuan Qiua and Jialong Yuana*

aTianjin Basechem Technology Co. Ltd, K1-4-404, No. 6 Haitaifazhan 6th Road Huayuan Industry Area, Tianjin New Technology Industry Park, Tianjin 300384, People's Republic of China
Correspondence e-mail: jialong.yuan@tjbasechem.com

The title molecule, C15H15Br2, has crystallographic m2m site symmetry. As a result, all atoms, except for those of the methyl groups, are exactly coplanar. In the crystal structure, there are weak [pi]-[pi] interactions with a centroid-centroid distance of 3.8409 (15) Å between symmetry-related molecules, which stack along the c axis.

Related literature

For applications of fluorene derivatives, see: Holder et al. (2005[Holder, E., Langeveld, B. M. W. & Schubert, U. S. (2005). Adv. Mater. 17, 1109-1121.]); Kulkarni et al. (2004[Kulkarni, A. P., Tonzola, C. J., Babel, A. & Jenekhe, S. A. (2004). Chem. Mater. 16, 4556-4573.]); Padmaperuma et al. (2006[Padmaperuma, A. B., Sapochak, L. S. & Burrows, P. E. (2006). Chem. Mater. 18, 2389-2396.]); Seneclauze et al. (2007[Seneclauze, J. B., Retailleau, P. & Ziessel, R. (2007). New J. Chem. 31, 1412-1416.]); Tsuboyama et al. (2003[Tsuboyama, A., Iwawaki, H., Furugori, M., Mukaide, T., Kamatani, J., Igawa, S., Moriyama, T., Miura, S., Takiguchi, T., Okada, S., Hoshino, M. & Ueno, K. (2003). J. Am. Chem. Soc. 125, 12971-12979.]). For the properties of fluorene-based molecules, see: Scherf & List (2002[Scherf, U. & List, E. J. W. (2002). Adv. Mater. 14, 447-487.]). For the synthesis of the title compound, see: Belfield et al. (2000[Belfield, K. D., Schafer, K. J., Mourad, W. & Reinhardt, B. A. (2000). J. Org. Chem. 65, 4475-4481.]).

[Scheme 1]

Experimental

Crystal data

  • C15H12Br2

  • Mr = 352.07

  • Orthorhombic, C m c m

  • a = 17.097 (4) Å

  • b = 11.161 (3) Å

  • c = 6.9120 (17) Å

  • V = 1319.0 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.12 mm-1

  • T = 296 K

  • 0.38 × 0.36 × 0.32 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.083, Tmax = 1.000

  • 3295 measured reflections

  • 662 independent reflections

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

  • Rint = 0.047
Refinement

  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.085

  • S = 1.05

  • 662 reflections

  • 54 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Data collection: SMART-NT (Bruker, 1998[Bruker (1998). SMART-NT and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 1998[Bruker (1998). SMART-NT and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; 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: DIAMOND (Brandenburg & Berndt, 1999[Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5021 ).

Acknowledgements

The authors acknowledge the Tianjin Binhai Hi-tech Industry Park Management Committee, Huayuan Industrial Park and Haitai Green Industrial Base for support of this work.

References

Belfield, K. D., Schafer, K. J., Mourad, W. & Reinhardt, B. A. (2000). J. Org. Chem. 65, 4475-4481.  [CrossRef] [PubMed] [ChemPort]
Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (1998). SMART-NT and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Holder, E., Langeveld, B. M. W. & Schubert, U. S. (2005). Adv. Mater. 17, 1109-1121.  [ISI] [CrossRef] [ChemPort]
Kulkarni, A. P., Tonzola, C. J., Babel, A. & Jenekhe, S. A. (2004). Chem. Mater. 16, 4556-4573.  [ISI] [CrossRef] [ChemPort]
Padmaperuma, A. B., Sapochak, L. S. & Burrows, P. E. (2006). Chem. Mater. 18, 2389-2396.  [ISI] [CSD] [CrossRef] [ChemPort]
Scherf, U. & List, E. J. W. (2002). Adv. Mater. 14, 447-487.  [ISI] [CrossRef]
Seneclauze, J. B., Retailleau, P. & Ziessel, R. (2007). New J. Chem. 31, 1412-1416.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tsuboyama, A., Iwawaki, H., Furugori, M., Mukaide, T., Kamatani, J., Igawa, S., Moriyama, T., Miura, S., Takiguchi, T., Okada, S., Hoshino, M. & Ueno, K. (2003). J. Am. Chem. Soc. 125, 12971-12979.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2010). E66, o1034  [ doi:10.1107/S1600536810012171 ]

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