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Volume 65 
Part 6 
Page o1220  
June 2009  

Received 3 April 2009
Accepted 28 April 2009
Online 7 May 2009


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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.006 Å
R = 0.035
wR = 0.090
Data-to-parameter ratio = 45.1
Details

1,2-Diiodo-4,5-dimethylbenzene

Bruce A. Hathaway,a* Uriah J. Kilgorea and Marcus R. Bonda

aDepartment of Chemistry, Southeast Missouri State University, Cape Girardeau, Missouri 63701, USA
Correspondence e-mail: bahathaway@semo.edu

The structure of the title compound, C8H8I2, conforms closely to the mm2 symmetry expected for the free molecule and is the first reported structure of a diiododimethylbenzene. Repulsion by neighboring I atoms and the neighboring methyl groups opposite to them results in a slight elongation of the molecule along the approximate twofold rotation axis that bisects the ring between the two I atoms. In the extended structure, the molecules form inversion-related pairs which are organized in approximately hexagonal close-packed layers and the layers then stacked so that molecules in neighboring layers abut head-to-tail in a manner that optimizes dipole-dipole interactions.

Related literature

For the synthesis see: Suzuki (1988[Suzuki, H. (1988). Org. Synth. 6, 700-704.]). For the structure of 1,2-diiodo-4,5-dimethoxybenzene, see: Cukiernik et al. (2008[Cukiernik, F. D., Zelcer, A., Garland, M. T. & Baggio, R. (2008). Acta Cryst. C64, o604-o608.]). For methods of iodinating substituted benzenes, see: Hathaway et al. (2007[Hathaway, B. A., White, K. L. & McGill, M. E. (2007). Synth. Commun. 37, 3855-3860.]). For related work on diacetylenes, see: Hathaway (1988[Hathaway, B. A. (1988). Molecules, 3, M75. http://www.mdpi.org/molbank/m0075.htm .]); Hathaway & Scates (1997[Hathaway, B. A. & Scates, A. M. (1997). J. Chem. Educ. 74, 111.]).

[Scheme 1]

Experimental

Crystal data

  • C8H8I2

  • Mr = 357.94

  • Monoclinic, P 21 /n

  • a = 9.4458 (1) Å

  • b = 8.1334 (1) Å

  • c = 13.4562 (2) Å

  • [beta] = 110.109 (1)°

  • V = 970.77 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.41 mm-1

  • T = 298 K

  • 0.3 × 0.2 × 0.18 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.184, Tmax = 0.316

  • 32763 measured reflections

  • 4243 independent reflections

  • 2520 reflections with I > 2[sigma](I)

  • Rint = 0.057
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.090

  • S = 1.10

  • 4243 reflections

  • 94 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.90 e Å-3

  • [Delta][rho]min = -0.75 e Å-3

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. London: Academic Press.]); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. London: Academic Press.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (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: IS2407 ).

Acknowledgements

The authors thank the National Science Foundation DUE CCLI-A&I program (grant No. 9951348) and Southeast Missouri State University for funding the X-ray diffraction facility.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Cukiernik, F. D., Zelcer, A., Garland, M. T. & Baggio, R. (2008). Acta Cryst. C64, o604-o608.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [details]
Hathaway, B. A. (1988). Molecules, 3, M75. http://www.mdpi.org/molbank/m0075.htm .
Hathaway, B. A. & Scates, A. M. (1997). J. Chem. Educ. 74, 111.
Hathaway, B. A., White, K. L. & McGill, M. E. (2007). Synth. Commun. 37, 3855-3860.  [CrossRef] [ChemPort]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. London: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Suzuki, H. (1988). Org. Synth. 6, 700-704.

Acta Cryst (2009). E65, o1220  [ doi:10.1107/S1600536809016018 ]

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