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Volume 68 
Part 11 
Page o3100  
November 2012  

Received 28 September 2012
Accepted 4 October 2012
Online 10 October 2012

Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.004 Å
R = 0.018
wR = 0.037
Data-to-parameter ratio = 15.5
Details
Open access

3,6-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 phenanthrene ring in the title compound, C14H8Br2, is approximately planar [maximum deviation = 0.039 (3) Å]. In contrast, the two bromo atoms are displaced slightly from the phenanthrene plane [maximum deviation = 0.1637 (3) Å]. In the crystal, the molecules adopt a herringbone-like arrangement and form face-to-face slipped [pi]-[pi] stacking interactions along the b axis, with an interplanar distance of 3.544 (3) Å and slippage of 1.81 Å. The crystal studied was a racemic twin with a minor twin fraction of 0.390 (10).

Related literature

For the synthesis of the title compound using the improved photocyclization of 4,4'-dibromo-trans-stilbene, see: Talele et al. (2009[Talele, H. R., Gohil, M. J. & Bedekar, A. V. (2009). Bull. Chem. Soc. Jpn, 82, 1182-1186.]). For the original synthesis and applications of the title compound, see: Nakamura et al. (1996[Nakamura, Y., Tsuihiji, T., Mita, T., Minowa, T., Tobita, S., Shizuka, H. & Nishimura, J. (1996). J. Am. Chem. Soc. 118, 1006-1012.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8Br2

  • Mr = 336.02

  • Monoclinic, P 21

  • a = 6.8697 (5) Å

  • b = 3.9809 (2) Å

  • c = 20.5002 (11) Å

  • [beta] = 93.813 (2)°

  • V = 559.39 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 7.21 mm-1

  • T = 223 K

  • 0.62 × 0.08 × 0.03 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.196, Tmax = 0.793

  • 5372 measured reflections

  • 2267 independent reflections

  • 2084 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.018

  • wR(F2) = 0.037

  • S = 1.00

  • 2267 reflections

  • 146 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 831 Friedel pairs

  • Flack parameter: 0.390 (10)

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: QK2043 ).


Acknowledgements

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

References

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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Nakamura, Y., Tsuihiji, T., Mita, T., Minowa, T., Tobita, S., Shizuka, H. & Nishimura, J. (1996). J. Am. Chem. Soc. 118, 1006-1012.  [CrossRef] [ChemPort] [ISI]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (1999). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Talele, H. R., Gohil, M. J. & Bedekar, A. V. (2009). Bull. Chem. Soc. Jpn, 82, 1182-1186.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3100  [ doi:10.1107/S1600536812041621 ]

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