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

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1431

doi:10.1107/S1600536812015930

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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

(Received 12 March 2012; accepted 12 April 2012; online 18 April 2012)

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 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 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
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.087
S = 1.07
1291 reflections
91 parameters
H-atom parameters constrained
Δρ_max = 1.34 e Å⁻³
Δρ_min = −0.76 e Å⁻³

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) -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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015930/ds2186sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812015930/ds2186Isup3.cml

checkCIF report

Comment top

The title co-crystal is part of a study on the halogen bond, which is a powerful intermolecular interaction we and others have used extensively to produce a variety of structures involving perfuorinated compounds (Ji et al. 2011; Arman et al. 2010; Cardillo et al. 2000), usually very diffcult to crystallize.

In the crystal structure, 1,2,4,5-tetrafluoro-3,6-diiodobenzene molecule is flat with the r.m.s. deviation of the 12 constituent atoms being 0.0062 Å (Fig. 1). It is noted that the cyclohexa-2,5-diene-1,4-dione molecule acts as a bidentate donor towards 1,2,4,5-tetrafluoro-3,6-diiodobenzene molecule, giving rise to chains extended throughout the whole crystal, in which the bond length of O···I halogen bond is 3.017 Å, as observed in the previous reports (Metrangolo et al. 2008; Ji et al. 2011).

In addition, the molecules are further stabilized in the crystal packing via a combination of C—H···F contacts (Table. 1), as shown in Fig. 2.

Related literature top

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 top

The starting materials were commercial obtained from Aldrich. The 1:1 adduct was obtained by dissolving in chloroform, at room temperature and in a vial, equimolecular amounts of cyclohexa-2,5-diene-1,4-dione and 1,2,4,5-tetrafluoro-3,6-diiodobenzene. The open vial was closed in a cylindrical bottle containing vaseline oil. Volatile solvents were allowed to diffuse at room temperature and, after one day, the yellow block crystals were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecular structure with atom numbering scheme and 30% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. A view in projection down the b axis showing the unit-cell contents. The O—I and C—H···F are shown as bule and purple dashed lines.

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

Crystal data top

C₆H₄O₂·C₆F₄I₂	Z = 1
M_r = 509.95	F(000) = 234
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0571P)²] where P = (F_o² + 2F_c²)/3
1291 reflections	(Δ/σ)_max < 0.001
91 parameters	Δρ_max = 1.34 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

C₆H₄O₂·C₆F₄I₂	γ = 97.781 (5)°
M_r = 509.95	V = 354.1 (3) Å³
Triclinic, P1	Z = 1
a = 5.778 (3) Å	Mo Kα radiation
b = 6.354 (3) Å	µ = 4.48 mm⁻¹
c = 10.013 (5) Å	T = 296 K
α = 102.295 (5)°	0.43 × 0.30 × 0.26 mm
β = 93.861 (5)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.07	Δρ_max = 1.34 e Å⁻³
1291 reflections	Δρ_min = −0.76 e Å⁻³
91 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₆H₄O₂·C₆F₄I₂
M_r	509.95
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.778 (3), 6.354 (3), 10.013 (5)
α, β, γ (°)	102.295 (5), 93.861 (5), 97.781 (5)
V (Å³)	354.1 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	4.48
Crystal size (mm)	0.43 × 0.30 × 0.26

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.249, 0.389
No. of measured, independent and observed [I > 2σ(I)] reflections	2585, 1291, 1096
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.087, 1.07
No. of reflections	1291
No. of parameters	91
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.34, −0.76

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z.

Acknowledgements

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

References

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