3,6-Dibromo­phenanthrene

Yokota, R.; Kitamura, C.; Kawase, T.

doi:10.1107/S1600536812041621

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 (C-C) = 0.004 Å
R = 0.018
wR = 0.037
Data-to-parameter ratio = 15.5
Details

3,6-Dibromophenanthrene

Ruri Yokota,^a Chitoshi Kitamura ^a ^* and Takeshi Kawase ^a

^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). For the original synthesis and applications of the title compound, see: Nakamura et al. (1996).

Experimental

Crystal data

C₁₄H₈Br₂
M_r = 336.02
Monoclinic, P 2₁
a = 6.8697 (5) Å
b = 3.9809 (2) Å
c = 20.5002 (11) Å
= 93.813 (2)°
V = 559.39 (6) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.196, T_max = 0.793
5372 measured reflections
2267 independent reflections
2084 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.018
wR(F²) = 0.037
S = 1.00
2267 reflections
146 parameters
1 restraint
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.46 e Å^-3
Absolute structure: Flack (1983), 831 Friedel pairs
Flack parameter: 0.390 (10)

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 ).

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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
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.
Talele, H. R., Gohil, M. J. & Bedekar, A. V. (2009). Bull. Chem. Soc. Jpn, 82, 1182-1186.

organic compounds