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Volume 68 
Part 1 
Page o5  
January 2012  

Received 29 September 2011
Accepted 25 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.025 Å
R = 0.091
wR = 0.258
Data-to-parameter ratio = 22.7
Details
Open access

1,2-Bis(dibromomethyl)benzene

aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
Correspondence e-mail: kyuchen@fcu.edu.tw

In the title compound, C8H6Br4, intramolecular C-H...Br hydrogen bonds generate two S(6) rings. The two geminal bromine-atom substituents point to opposite sides of the aromatic ring system. In the crystal, molecules are linked by intermolecular [pi]-[pi] interactions with centroid-centroid distances of 3.727 (9) and 3.858 (9) Å.

Related literature

For the preparation of the title compound, see: Ghorbani-Vaghei et al. (2009[Ghorbani-Vaghei, R., Chegini, M., Veisi, H. & Karimi-Tabar, M. (2009). Tetrahedron Lett. 50, 1861-1865.]). For its applications, see: Chen et al. (2002[Chen, K.-Y., Chow, T. J., Chou, P.-T., Cheng, Y.-M. & Tsai, S.-H. (2002). Tetrahedron Lett. 43, 8115-8119.], 2006[Chen, K.-Y., Hsieh, C.-C., Cheng, Y.-M., Lai, C.-H., Chou, P.-T. & Chow, T. J. (2006). J. Phys. Chem. A, 110, 12136-12144.], 2007[Chen, K.-Y., Hsing, H.-H., Wu, C.-C., Hwang, J.-J. & Chow, T. J. (2007). Chem. Commun. 10, 1065-1067.]); Chow et al. (2005[Chow, T. J., Pan, Y.-T., Yeh, Y.-S., Wen, Y.-S., Chen, K.-Y. & Chou, P.-T. (2005). Tetrahedron, 61, 6967-6975.]); Jansen et al. (2010[Jansen, G., Kahlert, B., Klärner, F.-G., Boese, R. & Bläser, D. (2010). J. Am. Chem. Soc., 132, 8581-8592.]); Pandithavidana et al. (2009[Pandithavidana, D. R., Poloukhtine, A. & Popik, V. V. (2009). J. Am. Chem. Soc. 131, 351-356.]); Swartz et al. (2005[Swartz, C. R., Parkin, S. R., Bullock, J. E., Anthony, J. E., Mayer, A. C. & Malliaras, G. G. (2005). Org. Lett. 7, 3163-3166.]). For related structures, see: Kus & Jones (2003)[Kus, P. & Jones, P. G. (2003). Acta Cryst. E59, o899-o900.]; Qin et al. (2005[Qin, S., Yin, G. & Zhou, B. (2005). Acta Cryst. E61, o3257-o3258.]); Sim et al. (2001[Sim, W., Lee, J. Y., Kim, J. S., Kim, J.-G. & Suh, I.-H. (2001). Acta Cryst. C57, 293-294.]). For graph-set theory, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C8H6Br4

  • Mr = 421.77

  • Triclinic, [P \overline 1]

  • a = 7.0222 (8) Å

  • b = 7.7313 (9) Å

  • c = 10.5927 (12) Å

  • [alpha] = 108.473 (10)°

  • [beta] = 97.108 (9)°

  • [gamma] = 90.394 (9)°

  • V = 540.61 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 14.83 mm-1

  • T = 297 K

  • 0.58 × 0.48 × 0.36 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.122, Tmax = 1.000

  • 4575 measured reflections

  • 2469 independent reflections

  • 1297 reflections with I > 2[sigma](I)

  • Rint = 0.073

Refinement
  • R[F2 > 2[sigma](F2)] = 0.091

  • wR(F2) = 0.258

  • S = 1.04

  • 2469 reflections

  • 109 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.62 e Å-3

  • [Delta][rho]min = -1.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8A...Br1 0.98 2.64 3.364 (16) 131
C8-H8A...Br2 0.98 2.78 3.420 (16) 124

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2031 ).


Acknowledgements

This work was supported by the National Science Council (NSC 99-2113-M-035-001-MY2) and Feng Chia University in Taiwan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, K.-Y., Chow, T. J., Chou, P.-T., Cheng, Y.-M. & Tsai, S.-H. (2002). Tetrahedron Lett. 43, 8115-8119.  [ISI] [CrossRef] [ChemPort]
Chen, K.-Y., Hsieh, C.-C., Cheng, Y.-M., Lai, C.-H., Chou, P.-T. & Chow, T. J. (2006). J. Phys. Chem. A, 110, 12136-12144.  [ISI] [CrossRef] [PubMed] [ChemPort]
Chen, K.-Y., Hsing, H.-H., Wu, C.-C., Hwang, J.-J. & Chow, T. J. (2007). Chem. Commun. 10, 1065-1067.  [CrossRef]
Chow, T. J., Pan, Y.-T., Yeh, Y.-S., Wen, Y.-S., Chen, K.-Y. & Chou, P.-T. (2005). Tetrahedron, 61, 6967-6975.  [ISI] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Ghorbani-Vaghei, R., Chegini, M., Veisi, H. & Karimi-Tabar, M. (2009). Tetrahedron Lett. 50, 1861-1865.  [ChemPort]
Jansen, G., Kahlert, B., Klärner, F.-G., Boese, R. & Bläser, D. (2010). J. Am. Chem. Soc., 132, 8581-8592.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Kus, P. & Jones, P. G. (2003). Acta Cryst. E59, o899-o900.  [CSD] [CrossRef] [details]
Pandithavidana, D. R., Poloukhtine, A. & Popik, V. V. (2009). J. Am. Chem. Soc. 131, 351-356.  [ISI] [CrossRef] [PubMed] [ChemPort]
Qin, S., Yin, G. & Zhou, B. (2005). Acta Cryst. E61, o3257-o3258.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sim, W., Lee, J. Y., Kim, J. S., Kim, J.-G. & Suh, I.-H. (2001). Acta Cryst. C57, 293-294.  [CSD] [CrossRef] [ChemPort] [details]
Swartz, C. R., Parkin, S. R., Bullock, J. E., Anthony, J. E., Mayer, A. C. & Malliaras, G. G. (2005). Org. Lett. 7, 3163-3166.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o5  [ doi:10.1107/S1600536811050616 ]

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