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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 [sigma](C-C) = 0.008 Å
R = 0.033
wR = 0.083
Data-to-parameter ratio = 18.4
Details
Open access

9,10-Diiodophenanthrene

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[Rodrígeuz-Lojo, D., Cobas, A., Peña, D., Pérez, D. & Guitián, E. (2012). Org. Lett. 14, 1363-1365.]). For a related structure, see: Yokota et al. (2012[Yokota, R., Kitamura, C. & Kawase, T. (2012). Acta Cryst. E68, o3174.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8I2

  • Mr = 430

  • Monoclinic, C 2/c

  • a = 18.094 (2) Å

  • b = 9.4557 (14) Å

  • c = 7.4187 (10) Å

  • [beta] = 111.953 (3)°

  • V = 1177.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.388, Tmax = 0.869

  • 5595 measured reflections

  • 1345 independent reflections

  • 1077 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.083

  • S = 1.12

  • 1345 reflections

  • 73 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.92 e Å-3

  • [Delta][rho]min = -0.92 e Å-3

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: 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.  [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]
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.  [ISI] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yokota, R., Kitamura, C. & Kawase, T. (2012). Acta Cryst. E68, o3174.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3323  [ doi:10.1107/S1600536812045758 ]

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