Cyclo­hexa-2,5-diene-1,4-dione–1,2,4,5-tetra­fluoro-3,6-diiodo­benzene (1/1)

Liu, P.; Ruan, C.; Li, T.; Ji, B.

doi:10.1107/S1600536812015930

Volume 68
Part 5
Page o1431
May 2012

Received 12 March 2012
Accepted 12 April 2012
Online 18 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.008 Å
R = 0.033
wR = 0.087
Data-to-parameter ratio = 14.2
Details

Cyclohexa-2,5-diene-1,4-dione-1,2,4,5-tetrafluoro-3,6-diiodobenzene (1/1)

Peng Liu,^a,^b Chuansheng Ruan,^a,^b Tiesheng Li ^a ^* and Baoming Ji ^b

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
Correspondence e-mail: lyhxxjbm@126.com

The asymmetric unit of the title co-crystal adduct, C₆H₄O₂·C₆F₄I₂, comprises a half-molecule each of cyclohexa-2,5-diene-1,4-dione and 1,2,4,5-tetrafluoro-3,6-diiodobenzene. The C₆F₄I₂ molecule is almost planar (r.m.s. deviation = 0.0062 Å). In the crystal, the components are connected through OI halogen bonds [3.017 (11) Å], leading to the formation of wavelike chains along the a axis. The crystal packing also features C-HF interactions.

Related literature

For related studies on co-crystal formation, see: Bhogala & Nangia (2008); Ji et al. (2011); Arman et al. (2010); Cardillo et al. (2000). For background to halogen bonding, see: Metrangolo et al. (2008).

Experimental

Crystal data

C₆H₄O₂·C₆F₄I₂
M_r = 509.95
Triclinic, $[P \overline 1]$
a = 5.778 (3) Å
b = 6.354 (3) Å
c = 10.013 (5) Å
= 102.295 (5)°
= 93.861 (5)°
= 97.781 (5)°
V = 354.1 (3) Å³
Z = 1
Mo K radiation
= 4.48 mm^-1
T = 296 K
0.43 × 0.30 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.249, T_max = 0.389
2585 measured reflections
1291 independent reflections
1096 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.087
S = 1.07
1291 reflections
91 parameters
H-atom parameters constrained
_max = 1.34 e Å^-3
_min = -0.76 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6F1ⁱ	0.93	2.64	3.562	171
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2186 ).

Acknowledgements

We are grateful to the National Natural Science Foundation of China (grant No. 21072089) for financial support.

References

Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2683.
Bhogala, B. R. & Nangia, A. (2008). New J. Chem. 32, 800-807.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cardillo, P., Corradi, E., Lunghi, A., Meille, S. V., Messina, M. T., Metrangolo, P. & Resnati, G. (2000). Tetrahedron, 56, 5535-5550.
Ji, B. M., Wang, W. Z., Deng, D. S. & Zhang, Y. (2011). Cryst. Growth Des. 11, 3622-3629.
Metrangolo, P., Resnati, G., Pilati, T. & Biella, S. (2008). Struct. Bond. 126, 105-136.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds