Cyclo-hexa-2,5-diene-1,4-dione-1,2,4,5-tetra-fluoro-3,6-diiodo-benzene (1/1).

The asymmetric unit of the title co-crystal adduct, C(6)H(4)O(2)·C(6)F(4)I(2), comprises a half-mol-ecule each of cyclo-hexa-2,5-diene-1,4-dione and 1,2,4,5-tetra-fluoro-3,6-diiodo-benzene. The C(6)F(4)I(2) mol-ecule is almost planar (r.m.s. deviation = 0.0062 Å). In the crystal, the components are connected through O⋯I halogen bonds [3.017 (11) Å], leading to the formation of wavelike chains along the a axis. The crystal packing also features C-H⋯F inter-actions.

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 = 509.95

Triclinic,

a = 5.778 (3) Å

b = 6.354 (3) Å

c = 10.013 (5) Å

α = 102.295 (5)°

β = 93.861 (5)°

γ = 97.781 (5)°

V = 354.1 (3) Å3

Z = 1

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 1.07

1291 reflections

91 parameters

H-atom parameters constrained

Δρmax = 1.34 e Å−3

Δρmin = −0.76 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015930/ds2186sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015930/ds2186Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015930/ds2186Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H4O2·C6F4I2	Z = 1
Mr = 509.95	F(000) = 234
Triclinic, P1	Dx = 2.391 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.778 (3) Å	Cell parameters from 1573 reflections
b = 6.354 (3) Å	θ = 3.3–25.5°
c = 10.013 (5) Å	µ = 4.48 mm−1
α = 102.295 (5)°	T = 296 K
β = 93.861 (5)°	Block, yellow
γ = 97.781 (5)°	0.43 × 0.30 × 0.26 mm
V = 354.1 (3) Å3

Bruker APEXII CCD diffractometer	1291 independent reflections
Radiation source: fine-focus sealed tube	1096 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
phi and ω scans	θmax = 25.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.249, Tmax = 0.389	k = −7→7
2585 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3
1291 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 1.34 e Å−3
0 restraints	Δρmin = −0.76 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.3224 (8)	0.5732 (8)	0.4260 (5)	0.0453 (11)
C2	0.3930 (9)	0.3726 (8)	0.3786 (5)	0.0466 (11)
C3	0.4339 (9)	0.6981 (8)	0.5494 (5)	0.0501 (12)
C4	0.5734 (10)	0.8493 (9)	0.0745 (6)	0.0593 (14)
C5	0.3440 (10)	0.8029 (10)	−0.0092 (6)	0.0652 (15)
H5	0.2464	0.6719	−0.0141	0.078*
C6	0.2763 (10)	0.9415 (10)	−0.0761 (6)	0.0612 (14)
H6	0.1296	0.9086	−0.1263	0.073*
F1	0.2901 (6)	0.2428 (6)	0.2593 (3)	0.0702 (9)
F2	0.3718 (6)	0.8922 (5)	0.6021 (4)	0.0712 (9)
I1	0.05048 (6)	0.67187 (6)	0.31973 (4)	0.06065 (19)
O1	0.6309 (10)	0.7170 (8)	0.1376 (5)	0.0898 (15)

	U11	U22	U33	U12	U13	U23
C1	0.045 (3)	0.048 (3)	0.043 (3)	0.0023 (19)	−0.003 (2)	0.014 (2)
C2	0.047 (3)	0.047 (3)	0.039 (3)	−0.002 (2)	−0.007 (2)	0.003 (2)
C3	0.054 (3)	0.045 (3)	0.047 (3)	0.003 (2)	0.001 (2)	0.004 (2)
C4	0.064 (3)	0.058 (3)	0.051 (3)	0.022 (3)	−0.013 (3)	0.000 (3)
C5	0.062 (3)	0.068 (4)	0.055 (3)	0.004 (3)	−0.011 (3)	0.001 (3)
C6	0.054 (3)	0.069 (4)	0.053 (3)	0.020 (3)	−0.017 (2)	−0.002 (3)
F1	0.076 (2)	0.067 (2)	0.0527 (18)	0.0096 (16)	−0.0214 (16)	−0.0097 (15)
F2	0.084 (2)	0.0544 (19)	0.068 (2)	0.0227 (16)	−0.0092 (17)	−0.0052 (16)
I1	0.0554 (3)	0.0678 (3)	0.0610 (3)	0.00885 (17)	−0.00837 (17)	0.02435 (19)
O1	0.108 (4)	0.073 (3)	0.085 (3)	0.027 (3)	−0.035 (3)	0.016 (2)

C1—C3	1.381 (7)	C4—O1	1.221 (7)
C1—C2	1.388 (7)	C4—C6ii	1.483 (9)
C1—I1	2.079 (5)	C4—C5	1.478 (8)
C2—F1	1.346 (5)	C5—C6	1.298 (9)
C2—C3i	1.373 (8)	C5—H5	0.9300
C3—F2	1.340 (6)	C6—C4ii	1.483 (9)
C3—C2i	1.373 (8)	C6—H6	0.9300
C3—C1—C2	116.9 (5)	O1—C4—C6ii	123.3 (5)
C3—C1—I1	122.0 (4)	O1—C4—C5	119.7 (6)
C2—C1—I1	121.0 (4)	C6ii—C4—C5	117.0 (5)
F1—C2—C3i	118.8 (5)	C6—C5—C4	121.2 (6)
F1—C2—C1	119.7 (4)	C6—C5—H5	119.4
C3i—C2—C1	121.6 (4)	C4—C5—H5	119.4
F2—C3—C2i	118.5 (4)	C5—C6—C4ii	121.8 (5)
F2—C3—C1	120.0 (5)	C5—C6—H6	119.1
C2i—C3—C1	121.6 (5)	C4ii—C6—H6	119.1
C3—C1—C2—F1	179.7 (5)	C2—C1—C3—C2i	0.2 (8)
I1—C1—C2—F1	2.5 (7)	I1—C1—C3—C2i	177.4 (4)
C3—C1—C2—C3i	−0.2 (8)	O1—C4—C5—C6	179.1 (6)
I1—C1—C2—C3i	−177.4 (4)	C6ii—C4—C5—C6	−1.2 (10)
C2—C1—C3—F2	−179.0 (5)	C4—C5—C6—C4ii	1.3 (10)
I1—C1—C3—F2	−1.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···F1iii	0.93	2.64	3.562	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯F1i	0.93	2.64	3.562	171

Symmetry code: (i) .