Received 28 September 2012
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 - 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).
For the synthesis of the title compound using the improved photocyclization of 4,4'-dibromo-trans-stilbene, see: Talele et al. (2009). For the original synthesis and applications of the title compound, see: Nakamura et al. (1996).
Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2043 ).
This work was supported by Grants-in-Aid for Scientific Research from the JSPS and MEXT.
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