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Volume 69 
Part 11 
Page o1641  
November 2013  

Received 10 September 2013
Accepted 10 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.017
wR = 0.039
Data-to-parameter ratio = 19.1
Details
Open access

(5Z,7Z,9Z)-5,10-Di­bromo­benzo[8]annulene

aDepartment of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, AB, T1K3M4, Canada
Correspondence e-mail: boere@uleth.ca

In the structure of the title compound, C12H8Br2, the two bromine substituents are oriented exo to the boat-shaped cyclo­octa­tetra­ene at the two ring sites that are [beta] to the ring fusion positions. The average Br-C bond distance is 1.919 (2) Å, the average distance for C=C double bonds that are Br substituted is 1.328 (2) Å, while the other two double-bond distances are 1.327 (2) and 1.398 (2) Å for the non-fused and fused bonds, respectively. Each type of ring inter­atomic distance is within s.u. of the average values for the four known structures, including the title compound, of benzo-fused cyclo­ocata­tetra­enes that are not coordinated to a metal atom. The crystal structure features short Br...Br [3.6620 (3) Å] and C...H [2.834 (2) and 2.841 (2) Å] contacts.

Related literature

For general background to photochemical conversions of benzo­cyclo­octa­tetra­enes, see: Bender et al. (1982[Bender, C. O., Bengtson, D. L., Dolman, D., Herle, C. E. L. & O'Shea, S. F. (1982). Can. J. Chem. 60, 1942-1952.], 1986[Bender, C. O., Bengtson, D. L., Dolman, D. & O'Shea, S. F. (1986). Can. J. Chem. 64, 237-245.], 1988[Bender, C. O., Dolman, D. & Murthy, G. K. (1988). Can. J. Chem. 66, 1656-1662.], 1991[Bender, C. O., Clyne, D. S. & Dolman, D. (1991). Can. J. Chem. 69, 70-76.]). For details of the synthesis, see: Barton et al. (1964[Barton, J. W., Henn, D. E., McLaughlan, K. A. & McOmie, J. F. W. (1964). J. Chem. Soc. pp. 1622-1625.]). For related structures, see: Bohshar et al. (1984[Bohshar, M., Maas, G., Heydt, H. & Regitz, M. (1984). Tetrahedron, 40, 5171-5176.]); Çelik et al. (2002[Çelik, I., Tutar, A., Akkurt, M., Özcan, Y. & Çakmak, O. (2002). Acta Cryst. E58, o314-o316.]); Jones et al. (1994[Jones, R., Scheffer, J. R., Trotter, J. & Yap, M. (1994). Acta Cryst. B50, 597-600.]), Kidokoro et al. (1983[Kidokoro, H., Saito, Y., Sato, M., Ebine, S., Sato, S., Hata, T. & Tamura, C. (1983). Bull. Chem. Soc. Jpn, 56, 1192-1195.]); Li et al. (1983[Li, W.-K., Chiu, S.-W., Mak, T. C. W. & Huang, N. Z. (1983). J. Mol. Struct. (THEOCHEM), 94, 285-291.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the PLATON suite of crystallographic software, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8Br2

  • Mr = 312.00

  • Monoclinic, P 21 /c

  • a = 8.5289 (5) Å

  • b = 8.3630 (5) Å

  • c = 15.5645 (9) Å

  • [beta] = 105.2980 (6)°

  • V = 1070.83 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 7.52 mm-1

  • T = 173 K

  • 0.16 × 0.09 × 0.08 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.510, Tmax = 0.746

  • 15053 measured reflections

  • 2426 independent reflections

  • 2217 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.017

  • wR(F2) = 0.039

  • S = 1.04

  • 2426 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXD (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5345 ).


Acknowledgements

This research was supported by the Natural Sciences and Engineering Research Council of Canada. The diffractometer at the University of Lethbridge X-ray Diffraction Facility was purchased with the help of NSERC and the University.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Barton, J. W., Henn, D. E., McLaughlan, K. A. & McOmie, J. F. W. (1964). J. Chem. Soc. pp. 1622-1625.  [CrossRef]
Bender, C. O., Bengtson, D. L., Dolman, D., Herle, C. E. L. & O'Shea, S. F. (1982). Can. J. Chem. 60, 1942-1952.  [CrossRef] [ChemPort] [Web of Science]
Bender, C. O., Bengtson, D. L., Dolman, D. & O'Shea, S. F. (1986). Can. J. Chem. 64, 237-245.  [CrossRef] [ChemPort] [Web of Science]
Bender, C. O., Clyne, D. S. & Dolman, D. (1991). Can. J. Chem. 69, 70-76.  [CrossRef] [ChemPort] [Web of Science]
Bender, C. O., Dolman, D. & Murthy, G. K. (1988). Can. J. Chem. 66, 1656-1662.  [CrossRef] [ChemPort] [Web of Science]
Bohshar, M., Maas, G., Heydt, H. & Regitz, M. (1984). Tetrahedron, 40, 5171-5176.
Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Çelik, I., Tutar, A., Akkurt, M., Özcan, Y. & Çakmak, O. (2002). Acta Cryst. E58, o314-o316.  [CSD] [CrossRef] [IUCr Journals]
Jones, R., Scheffer, J. R., Trotter, J. & Yap, M. (1994). Acta Cryst. B50, 597-600.  [CSD] [CrossRef] [IUCr Journals]
Kidokoro, H., Saito, Y., Sato, M., Ebine, S., Sato, S., Hata, T. & Tamura, C. (1983). Bull. Chem. Soc. Jpn, 56, 1192-1195.  [CrossRef] [ChemPort] [Web of Science]
Li, W.-K., Chiu, S.-W., Mak, T. C. W. & Huang, N. Z. (1983). J. Mol. Struct. (THEOCHEM), 94, 285-291.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1641  [ doi:10.1107/S1600536813027797 ]

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