2,2′-Diiodo­azobenzene

Elder, P.J.W.; Vargas-Baca, I.

doi:10.1107/S1600536812040718

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 (C-C) = 0.004 Å
R = 0.027
wR = 0.059
Data-to-parameter ratio = 22.0
Details

2,2'-Diiodoazobenzene

Philip J. W. Elder ^a and Ignacio Vargas-Baca ^a ^*

^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 CC distance = 3.383 (4) Å].

Related literature

For analogous 2,2'-dichloroazobenzenes, see: Komeyama et al. (1973); Crispini et al. (1998). For the structure of a related o-halogenated azobenzene, see: Wragg et al. (2011).

Experimental

Crystal data

C₁₂H₈I₂N₂
M_r = 433.88
Monoclinic, P 2₁ /c
a = 4.6306 (3) Å
b = 18.1105 (12) Å
c = 15.3748 (10) Å
= 98.532 (1)°
V = 1275.10 (14) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.322, T_max = 0.873
16726 measured reflections
3186 independent reflections
2536 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.059
S = 1.03
3186 reflections
145 parameters
H-atom parameters constrained
_max = 0.56 e Å^-3
_min = -0.56 e Å^-3

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); 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.
Komeyama, M., Yamamoto, S., Nishimura, N. & Hasegawa, S. (1973). Bull. Chem. Soc. Jpn, 46, 2606-2607.
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.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wragg, D. S., Ahmed, M. A. K., Nilsen, O. & Fjellvåg, H. (2011). Acta Cryst. E67, o2326.

organic compounds