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Volume 68 
Part 11 
Page o3174  
November 2012  

Received 5 October 2012
Accepted 10 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.008 Å
R = 0.033
wR = 0.116
Data-to-parameter ratio = 17.2
Details
Open access

9,10-Dibromophenanthrene

aDepartment of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan
Correspondence e-mail: kitamura@eng.u-hyogo.ac.jp

The molecule of the title compound, C14H8Br2, is almost planar [maximum deviation 0.0355 (7) Å] and possesses crystallographic twofold (C2) symmetry. In the crystal, the molecules form face-to-face slipped antiparallel [pi]-[pi] stacking interactions along the c axis with an interplanar distance 3.471 (7) Å, centroid-centroid distances of 3.617 (5)-3.803 (6) Å.

Related literature

For the first synthesis of the title compound, see: Schmidt & Ladner (1904[Schmidt, J. & Ladner, G. (1904). Chem. Ber. 37, 4402-4405.]). For the synthesis of 2,2'-bis(dibromomethyl)biphenyl, see: Bacon & Bankhead (1963[Bacon, R. G. R. & Bankhead, R. (1963). J. Chem. Soc. pp. 839-845.]). For a related structure, see: Yokota et al. (2012[Yokota, R., Kitamura, C. & Kawase, T. (2012). Acta Cryst. E68, o3100.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8Br2

  • Mr = 336.02

  • Monoclinic, C 2/c

  • a = 18.2630 (15) Å

  • b = 9.0963 (8) Å

  • c = 7.3025 (6) Å

  • [beta] = 114.499 (2)°

  • V = 1103.91 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 7.31 mm-1

  • T = 223 K

  • 0.5 × 0.1 × 0.08 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.160, Tmax = 0.558

  • 5151 measured reflections

  • 1257 independent reflections

  • 1011 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.116

  • S = 1.25

  • 1257 reflections

  • 73 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.67 e Å-3

  • [Delta][rho]min = -1.49 e Å-3

Data collection: RAPID-AUTO (Rigaku, 1999[Rigaku (1999). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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: RZ5013 ).


Acknowledgements

This work was supported by Grants-in-Aid for Scientific Research from the JSPS and MEXT.

References

Bacon, R. G. R. & Bankhead, R. (1963). J. Chem. Soc. pp. 839-845.  [CrossRef]
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (1999). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Schmidt, J. & Ladner, G. (1904). Chem. Ber. 37, 4402-4405.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yokota, R., Kitamura, C. & Kawase, T. (2012). Acta Cryst. E68, o3100.  [CrossRef] [details]


Acta Cryst (2012). E68, o3174  [ doi:10.1107/S1600536812042353 ]

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