[Journal logo]

Volume 68 
Part 11 
Page o3127  
November 2012  

Received 24 September 2012
Accepted 26 September 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.027
wR = 0.059
Data-to-parameter ratio = 22.0
Details
Open access

2,2'-Diiodoazobenzene

aDepartment of Chemistry and Chemical Biology, McMaster University, 1280 Main, Street West, Hamilton, Ontario, Canada L8S 4M1
Correspondence e-mail: vargas@chemistry.mcmaster.ca

The molecular structure of the title compound, C12H8I2N2 [systematic name: (E)-bis(2-iodophenyl)diazene], exhibits an essentially planar trans geometry [maximum deviation = 0.022 (4) Å] with the iodine atoms ortho to the azo bridge. In the crystal, offset [pi]-stacking leads to the formation of columns along the a axis [closest C...C distance = 3.383 (4) Å].

Related literature

For analogous 2,2'-dichloroazobenzenes, see: Komeyama et al. (1973[Komeyama, M., Yamamoto, S., Nishimura, N. & Hasegawa, S. (1973). Bull. Chem. Soc. Jpn, 46, 2606-2607.]); Crispini et al. (1998[Crispini, A., Ghedini, M. & Pucci, D. (1998). Acta Cryst. C54, 1869-1871.]). For the structure of a related o-halogenated azobenzene, see: Wragg et al. (2011[Wragg, D. S., Ahmed, M. A. K., Nilsen, O. & Fjellvåg, H. (2011). Acta Cryst. E67, o2326.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8I2N2

  • Mr = 433.88

  • Monoclinic, P 21 /c

  • a = 4.6306 (3) Å

  • b = 18.1105 (12) Å

  • c = 15.3748 (10) Å

  • [beta] = 98.532 (1)°

  • V = 1275.10 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.91 mm-1

  • T = 296 K

  • 0.63 × 0.09 × 0.04 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: analytical (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.322, Tmax = 0.873

  • 16726 measured reflections

  • 3186 independent reflections

  • 2536 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.059

  • S = 1.03

  • 3186 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5154 ).


Acknowledgements

The authors are grateful for financial support from the Natural Sciences and Engineering Research Council of Canada (NSERC).

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Crispini, A., Ghedini, M. & Pucci, D. (1998). Acta Cryst. C54, 1869-1871.  [CSD] [CrossRef] [details]
Komeyama, M., Yamamoto, S., Nishimura, N. & Hasegawa, S. (1973). Bull. Chem. Soc. Jpn, 46, 2606-2607.  [CrossRef] [ChemPort] [ISI]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wragg, D. S., Ahmed, M. A. K., Nilsen, O. & Fjellvåg, H. (2011). Acta Cryst. E67, o2326.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3127  [ doi:10.1107/S1600536812040718 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.