9,10-Diiodo­phenanthrene

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

doi:10.1107/S1600536812045758

Volume 68
Part 12
Page o3323
December 2012

Received 10 October 2012
Accepted 5 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.008 Å
R = 0.033
wR = 0.083
Data-to-parameter ratio = 18.4
Details

9,10-Diiodophenanthrene

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 whole molecule of the title compound, C₁₄H₈I₂, is generated by crystallographic twofold symmetry. The molecule is planar [maximum deviation = 0.0323 (6) Å] with the I atoms displaced from the mean plane of the phenanthrene ring system by only 0.0254 (5) Å. In the crystal, molecules form face-to-face slipped antiparallel [pi] - [pi] stacking interactions along the c axis with an interplanar distance of 3.499 (7) Å.

Related literature

For the synthesis of the title compound, see: Rodrígeuz-Lojo et al. (2012). For a related structure, see: Yokota et al. (2012).

Experimental

Crystal data

C₁₄H₈I₂
M_r = 430
Monoclinic, C 2/c
a = 18.094 (2) Å
b = 9.4557 (14) Å
c = 7.4187 (10) Å
= 111.953 (3)°
V = 1177.2 (3) Å³
Z = 4
Mo K radiation
= 5.31 mm^-1
T = 223 K
0.52 × 0.08 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999) T_min = 0.388, T_max = 0.869
5595 measured reflections
1345 independent reflections
1077 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.083
S = 1.12
1345 reflections
73 parameters
H-atom parameters constrained
_max = 0.92 e Å^-3
_min = -0.92 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: JJ2155 ).

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.
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (1999). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rodrígeuz-Lojo, D., Cobas, A., Peña, D., Pérez, D. & Guitián, E. (2012). Org. Lett. 14, 1363-1365.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yokota, R., Kitamura, C. & Kawase, T. (2012). Acta Cryst. E68, o3174.

organic compounds