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Volume 68 
Part 12 
Page o3391  
December 2012  

Received 27 October 2012
Accepted 11 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.035
wR = 0.039
Data-to-parameter ratio = 32.4
Details
Open access

Iododurene

aLaboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, 25000 Constantine, Algeria, and bUMR 6226 CNRS-Université Rennes 1, Sciences Chimiques de Rennes, Equipe Matière Condensée et Systèmes Electroactifs, 263 Avenue du Général Leclerc, F-35042 Rennes, France
Correspondence e-mail: n_hamdouni@yahoo.fr

The title compound (systematic name: 1-iodo-2,3,5,6-tetramethylbenzene), C10H13I, crystallizes in the chiral space group P212121. The I atom is displaced by 0.1003 (5) Å from the mean plane of the ten C atoms [maximum deviation = 0.018 (6) Å]. In the crystal, there are no significant intermolecular interactions present.

Related literature

For the crystal structure of bromodurene, see: Charbonneau et al. (1964[Charbonneau, G., Baudour, J., Messager, J. C. & Meinnel, J. (1964). Acta Cryst. 17, 780-781.], 1965[Charbonneau, G., Baudour, J., Messager, J. C. & Meinnel, J. (1965). Bull. Soc. Fr. Minéral. Cristallogr. 88, 147-148.]). For the physical properties of mono-halogenated derivatives of durene, see: Balcou et al. (1965[Balcou, Y., Grégoire, P. & Meinnel, J. (1965). J. Chim. Phys. PCB, 62, 536-538.]). For standard bond lengths in similar compounds, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Hope et al. (1970[Hope, H., Knobler, C. & McCullough, J. D. (1970). Acta Cryst. B26, 628-640.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13I

  • Mr = 260.11

  • Orthorhombic, P 21 21 21

  • a = 5.5099 (3) Å

  • b = 11.8839 (5) Å

  • c = 15.1704 (6) Å

  • V = 993.34 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.16 mm-1

  • T = 293 K

  • 0.10 × 0.05 × 0.04 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.140, Tmax = 0.193

  • 26027 measured reflections

  • 2271 independent reflections

  • 2036 reflections with I > 3[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.039

  • S = 1.04

  • 3272 reflections

  • 101 parameters

  • 36 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.84 e Å-3

  • [Delta][rho]min = -0.71 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 925 Friedal pairs

  • Flack parameter: -0.03 (4)

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR2002 (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: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]) and DIAMOND (Brandenburg, 2012[Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: CRYSTALS.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2521 ).


Acknowledgements

The authors thank the Centre de Diffractométrie de l'Université de Rennes 1 for the opportunity to collect data on the Nonius Kappa CCD X-ray diffractometer. We would also like to thank Dr Olivier Jeannin for the useful advice he provided.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Balcou, Y., Grégoire, P. & Meinnel, J. (1965). J. Chim. Phys. PCB, 62, 536-538.  [ChemPort]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [ISI] [CrossRef] [details]
Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
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]
Charbonneau, G., Baudour, J., Messager, J. C. & Meinnel, J. (1964). Acta Cryst. 17, 780-781.  [CrossRef] [ChemPort] [details]
Charbonneau, G., Baudour, J., Messager, J. C. & Meinnel, J. (1965). Bull. Soc. Fr. Minéral. Cristallogr. 88, 147-148.  [ChemPort]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hope, H., Knobler, C. & McCullough, J. D. (1970). Acta Cryst. B26, 628-640.  [CrossRef] [ChemPort] [details] [ISI]
Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.


Acta Cryst (2012). E68, o3391  [ doi:10.1107/S1600536812046557 ]

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