9,10-Dibromo­phenanthrene

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

doi:10.1107/S1600536812042353

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 (C-C) = 0.008 Å
R = 0.033
wR = 0.116
Data-to-parameter ratio = 17.2
Details

9,10-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 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). For the synthesis of 2,2'-bis(dibromomethyl)biphenyl, see: Bacon & Bankhead (1963). For a related structure, see: Yokota et al. (2012).

Experimental

Crystal data

C₁₄H₈Br₂
M_r = 336.02
Monoclinic, C 2/c
a = 18.2630 (15) Å
b = 9.0963 (8) Å
c = 7.3025 (6) Å
= 114.499 (2)°
V = 1103.91 (16) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.160, T_max = 0.558
5151 measured reflections
1257 independent reflections
1011 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.116
S = 1.25
1257 reflections
73 parameters
H-atom parameters constrained
_max = 0.67 e Å^-3
_min = -1.49 e Å^-3

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: 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.
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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yokota, R., Kitamura, C. & Kawase, T. (2012). Acta Cryst. E68, o3100.

organic compounds