Poly[bis­(ethanol)(μ4-2,3,5,6-tetra­fluoro­benzene-1,4-di­carboxyl­ato)cadmium]

Ko, N.; Kim, J.

doi:10.1107/S1600536813026287

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages m577-m578

doi:10.1107/S1600536813026287

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Poly[bis(ethanol)(μ₄-2,3,5,6-tetrafluorobenzene-1,4-dicarboxylato)cadmium]

Nakeun Ko ^a and Jaheon Kim ^a ^*

^aDepartment of Chemistry, Soongsil University, 369 Sangdo-Ro, Dongjak-Gu, Seoul, 156-743, South Korea
^*Correspondence e-mail: jaheon@ssu.ac.kr

(Received 19 September 2013; accepted 23 September 2013; online 2 October 2013)

In the title compound, [Cd(C₈F₄O₄)(C₂H₅OH)₂]_n, the Cd^II cation sits on an inversion centre and is coordinated by six O atoms from four tetrafluorobenzene-1,4-dicarboxylate anions and two ethanol molecules in a distorted octahedral geometry. The anionic ligand is also located on an inversion centre, and connects four Cd^II cations, generating a two-dimensional polymeric layer parallel to the ab plane. Within the layer, the ethanol molecule links F and O atoms of the nearest anionic ligands via O—H⋯O and O—H⋯F hydrogen bonds. The ethyl group of the ethanol molecule is disordered over two positions with an occupancy ratio of 0.567 (10):0.433 (10).

CCDC reference: 962922

Related literature

For metal-organic frameworks composed of metal ions and 2,3,5,6-tetrafluorobenzene-1,4-dicarboxylate (or tetrafluoroterephthalate), see: Chen et al. (2006 , 2009 ); Hulvey, Ayala et al. (2009 ); Hulvey, Ayala & Cheetham et al. (2009 ); Hulvey, Falco et al. (2009 ); Hulvey et al. (2011 ); Kitaura et al. (2004 ); MacNeill et al. (2011 ); Mikhalyova et al. (2011 ); Seidel et al. (2011 ); Seidel et al. (2012 ); Yoon et al. (2007 ); Yu et al. (2011 ); Zheng et al. (2008 ); Zhu et al. (2009 ).

Experimental

Crystal data

[Cd(C₈F₄O₄)(C₂H₆O)₂]
M_r = 440.61
Triclinic, $[P \overline 1]$
a = 4.8367 (3) Å
b = 9.0903 (6) Å
c = 9.4078 (6) Å
α = 108.091 (1)°
β = 100.637 (1)°
γ = 102.275 (1)°
V = 369.95 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.55 mm⁻¹
T = 173 K
0.35 × 0.20 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.613, T_max = 0.913
2308 measured reflections
1576 independent reflections
1569 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.054
S = 1.11
1576 reflections
131 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O1	2.2526 (15)
Cd1—O2ⁱ	2.3194 (15)
Cd1—O3	2.2929 (18)
Symmetry code: (i) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3OA⋯O2ⁱⁱ	0.85 (1)	1.94 (2)	2.719 (2)	152 (4)
O3—H3OB⋯F2ⁱ	0.85 (1)	2.40 (2)	3.196 (2)	156 (4)
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+1, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 962922

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813026287/xu5740sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026287/xu5740Isup2.hkl

checkCIF report

Comment top

We reported previously a metal-organic framework (MOF) composed of iron ions and 2,3,5,6-tetrafluorobenzene-1,4-dicarboxylate (or tetrafluoroterephthalate) linkers (Yoon et al., 2007). The title compound in this work was obtained in the course of making a new MOF using cadmium ion with the same organic linker. However, unlike other MOFs prepared through solvothermal reactions in common amine solvent such as N,N-dimethylformamide, the title compound could be obtained as single crystals in hot ethanol.

Related literature top

For metal-organic frameworks composed of metal ions and 2,3,5,6-tetrafluorobenzene-1,4-dicarboxylate (or tetrafluoroterephthalate), see: Chen et al. (2006, 2009); Hulvey, Ayala et al. (2009); Hulvey, Ayala & Cheetham et al. (2009); Hulvey, Falco et al. (2009); Hulvey et al. (2011); Kitaura et al. (2004); MacNeill et al. (2011); Mikhalyova et al. (2011); Seidel et al. (2011); Seidel et al. (2012); Yoon et al. (2007); Yu et al. (2011); Zheng et al. (2008); Zhu et al. (2009).

Experimental top

The title compound was obtained as colorless plate crystals by a solvothermal reaction between cadmium(II) nitrate tetrahydrate (25 mg) and tetrafluorobenzene-1,4-dicarboxylic acid (12 mg) in ethanol (8 ml)in a Teflon-lined vessel (23 ml) at 353 K and for 2 days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. An asymmetric unit of the title compound is shown with the atomic numbering scheme. Displacement ellipsoids are drawn at 50% probability level.
	Fig. 2. The coordination environment of the title compound is shown with H-bonds (dotted lines).
	Fig. 3. A packing diagram of the title compound is displayed along the c axis. Hydrogen bonds are shown with light blue dotted lines.
	Fig. 4. A packing diagram of the title compound is displayed along the a axis. Hydrogen bonds are shown with light blue dotted lines.

Poly[bis(ethanol)(µ₄-2,3,5,6-tetrafluorobenzene-1,4-dicarboxylato)cadmium] top

Crystal data top

[Cd(C₈F₄O₄)(C₂H₆O)₂]	Z = 1
M_r = 440.61	F(000) = 216
Triclinic, P1	D_x = 1.978 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8367 (3) Å	Cell parameters from 2269 reflections
b = 9.0903 (6) Å	θ = 2.4–28.2°
c = 9.4078 (6) Å	µ = 1.55 mm⁻¹
α = 108.091 (1)°	T = 173 K
β = 100.637 (1)°	Plate, colorless
γ = 102.275 (1)°	0.35 × 0.20 × 0.06 mm
V = 369.95 (4) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	1576 independent reflections
Radiation source: fine-focus sealed tube	1569 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
phi and ω scans	θ_max = 27.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→6
T_min = 0.613, T_max = 0.913	k = −11→11
2308 measured reflections	l = −12→8

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.020	w = 1/[σ²(F_o²) + (0.0317P)² + 0.1686P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.054	(Δ/σ)_max < 0.001
S = 1.11	Δρ_max = 0.40 e Å⁻³
1576 reflections	Δρ_min = −0.54 e Å⁻³
131 parameters

Crystal data top

[Cd(C₈F₄O₄)(C₂H₆O)₂]	γ = 102.275 (1)°
M_r = 440.61	V = 369.95 (4) Å³
Triclinic, P1	Z = 1
a = 4.8367 (3) Å	Mo Kα radiation
b = 9.0903 (6) Å	µ = 1.55 mm⁻¹
c = 9.4078 (6) Å	T = 173 K
α = 108.091 (1)°	0.35 × 0.20 × 0.06 mm
β = 100.637 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	1576 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1569 reflections with I > 2σ(I)
T_min = 0.613, T_max = 0.913	R_int = 0.014
2308 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	6 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.40 e Å⁻³
1576 reflections	Δρ_min = −0.54 e Å⁻³
131 parameters

Special details top

Geometry. 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 > 2sigma(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	Occ. (<1)
Cd1	1.0000	0.5000	1.0000	0.02063 (9)
F1	0.1389 (4)	0.24768 (17)	1.27515 (16)	0.0358 (3)
F2	0.2660 (3)	0.01945 (17)	0.77434 (17)	0.0349 (3)
O1	0.6687 (3)	0.28942 (19)	1.0084 (2)	0.0271 (3)
O2	0.3899 (3)	0.43185 (17)	1.12102 (18)	0.0227 (3)
C1	0.4446 (4)	0.3017 (2)	1.0543 (2)	0.0205 (4)
C2	0.2191 (4)	0.1450 (2)	1.0267 (2)	0.0194 (4)
C3	0.0738 (5)	0.1268 (3)	1.1375 (2)	0.0226 (4)
C4	0.1397 (5)	0.0137 (3)	0.8888 (3)	0.0219 (4)
O3	1.0823 (4)	0.3384 (2)	0.7802 (2)	0.0327 (4)
H3OA	1.249 (5)	0.393 (5)	0.781 (5)	0.039*	0.567 (10)
H3OB	1.137 (15)	0.267 (5)	0.809 (5)	0.039*	0.433 (10)
C5	0.8671 (16)	0.2366 (7)	0.6350 (7)	0.055 (2)	0.567 (10)
H5A	0.6914	0.1769	0.6553	0.065*	0.567 (10)
H5B	0.9502	0.1568	0.5726	0.065*	0.567 (10)
C6	0.783 (2)	0.3392 (10)	0.5484 (8)	0.094 (4)	0.567 (10)
H6A	0.6335	0.2711	0.4509	0.141*	0.567 (10)
H6B	0.9566	0.3951	0.5257	0.141*	0.567 (10)
H6C	0.7039	0.4190	0.6115	0.141*	0.567 (10)
C5A	0.9372 (18)	0.3012 (15)	0.6188 (7)	0.064 (3)	0.433 (10)
H5AA	0.9215	0.4015	0.6017	0.076*	0.433 (10)
H5AB	1.0524	0.2508	0.5514	0.076*	0.433 (10)
C6A	0.6405 (16)	0.1883 (14)	0.5801 (9)	0.077 (4)	0.433 (10)
H6AA	0.5410	0.1599	0.4705	0.116*	0.433 (10)
H6AB	0.5261	0.2403	0.6452	0.116*	0.433 (10)
H6AC	0.6579	0.0902	0.5990	0.116*	0.433 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01309 (12)	0.01499 (12)	0.03701 (14)	0.00397 (8)	0.01226 (8)	0.01066 (9)
F1	0.0477 (9)	0.0235 (7)	0.0292 (7)	−0.0016 (6)	0.0166 (6)	0.0042 (6)
F2	0.0434 (8)	0.0268 (7)	0.0387 (7)	0.0039 (6)	0.0284 (6)	0.0117 (6)
O1	0.0160 (7)	0.0204 (8)	0.0512 (10)	0.0062 (6)	0.0155 (7)	0.0174 (7)
O2	0.0184 (7)	0.0165 (7)	0.0331 (8)	0.0035 (6)	0.0083 (6)	0.0094 (6)
C1	0.0137 (9)	0.0186 (10)	0.0310 (10)	0.0029 (7)	0.0061 (7)	0.0127 (8)
C2	0.0128 (8)	0.0175 (9)	0.0320 (10)	0.0050 (7)	0.0081 (7)	0.0131 (8)
C3	0.0214 (10)	0.0188 (10)	0.0273 (10)	0.0045 (8)	0.0079 (8)	0.0079 (8)
C4	0.0196 (10)	0.0219 (10)	0.0302 (10)	0.0063 (8)	0.0140 (8)	0.0132 (8)
O3	0.0258 (8)	0.0301 (9)	0.0332 (9)	0.0046 (7)	0.0055 (7)	0.0032 (7)
C5	0.051 (5)	0.033 (3)	0.049 (3)	−0.001 (3)	−0.009 (3)	−0.005 (3)
C6	0.109 (7)	0.128 (8)	0.040 (4)	0.079 (7)	0.002 (4)	0.004 (4)
C5A	0.053 (5)	0.072 (7)	0.033 (4)	−0.028 (5)	−0.004 (3)	0.015 (4)
C6A	0.033 (4)	0.124 (9)	0.036 (4)	−0.017 (5)	0.000 (3)	0.009 (4)

Geometric parameters (Å, º) top

Cd1—O1ⁱ	2.2526 (15)	O3—C5	1.444 (4)
Cd1—O1	2.2526 (15)	O3—C5A	1.449 (5)
Cd1—O2ⁱⁱ	2.3194 (15)	O3—H3OA	0.850 (5)
Cd1—O2ⁱⁱⁱ	2.3194 (15)	O3—H3OB	0.849 (5)
Cd1—O3ⁱ	2.2929 (18)	C5—C6	1.487 (5)
Cd1—O3	2.2929 (18)	C5—H5A	0.9900
F1—C3	1.343 (3)	C5—H5B	0.9900
F2—C4	1.342 (2)	C6—H6A	0.9800
O1—C1	1.252 (3)	C6—H6B	0.9800
O2—C1	1.264 (3)	C6—H6C	0.9800
O2—Cd1^iv	2.3194 (15)	C5A—C6A	1.481 (5)
C1—C2	1.513 (3)	C5A—H5AA	0.9900
C2—C4	1.384 (3)	C5A—H5AB	0.9900
C2—C3	1.391 (3)	C6A—H6AA	0.9800
C3—C4^v	1.382 (3)	C6A—H6AB	0.9800
C4—C3^v	1.382 (3)	C6A—H6AC	0.9800

O1ⁱ—Cd1—O1	180.0	C5—O3—H3OA	120 (3)
O1ⁱ—Cd1—O3ⁱ	91.52 (7)	C5A—O3—H3OA	97 (3)
O1—Cd1—O3ⁱ	88.48 (6)	Cd1—O3—H3OA	103 (3)
O1ⁱ—Cd1—O3	88.48 (6)	C5—O3—H3OB	100 (4)
O1—Cd1—O3	91.52 (7)	C5A—O3—H3OB	120 (3)
O3ⁱ—Cd1—O3	180.0	Cd1—O3—H3OB	103 (3)
O1ⁱ—Cd1—O2ⁱⁱ	87.93 (6)	H3OA—O3—H3OB	98 (6)
O1—Cd1—O2ⁱⁱ	92.07 (6)	O3—C5—C6	109.1 (5)
O3ⁱ—Cd1—O2ⁱⁱ	97.63 (6)	O3—C5—H5A	109.9
O3—Cd1—O2ⁱⁱ	82.37 (6)	C6—C5—H5A	109.9
O1ⁱ—Cd1—O2ⁱⁱⁱ	92.07 (5)	O3—C5—H5B	109.9
O1—Cd1—O2ⁱⁱⁱ	87.93 (6)	C6—C5—H5B	109.9
O3ⁱ—Cd1—O2ⁱⁱⁱ	82.37 (6)	H5A—C5—H5B	108.3
O3—Cd1—O2ⁱⁱⁱ	97.63 (6)	C5—C6—H6A	109.5
O2ⁱⁱ—Cd1—O2ⁱⁱⁱ	180.0	C5—C6—H6B	109.5
C1—O1—Cd1	123.39 (14)	H6A—C6—H6B	109.5
C1—O2—Cd1^iv	120.48 (13)	C5—C6—H6C	109.5
O1—C1—O2	126.19 (19)	H6A—C6—H6C	109.5
O1—C1—C2	116.46 (19)	H6B—C6—H6C	109.5
O2—C1—C2	117.36 (18)	C6A—C5A—O3	108.5 (5)
C4—C2—C3	116.23 (19)	C6A—C5A—H5AA	110.0
C4—C2—C1	122.13 (19)	O3—C5A—H5AA	110.0
C3—C2—C1	121.62 (19)	C6A—C5A—H5AB	110.0
F1—C3—C4^v	117.7 (2)	O3—C5A—H5AB	110.0
F1—C3—C2	120.24 (19)	H5AA—C5A—H5AB	108.4
C4^v—C3—C2	122.0 (2)	C5A—C6A—H6AA	109.5
F2—C4—C3^v	117.5 (2)	C5A—C6A—H6AB	109.5
F2—C4—C2	120.81 (19)	H6AA—C6A—H6AB	109.5
C3^v—C4—C2	121.7 (2)	C5A—C6A—H6AC	109.5
C5—O3—Cd1	127.3 (4)	H6AA—C6A—H6AC	109.5
C5A—O3—Cd1	129.2 (6)	H6AB—C6A—H6AC	109.5

Cd1—O1—C1—O2	−10.2 (3)	C4—C2—C3—C4^v	−0.6 (3)
Cd1—O1—C1—C2	169.78 (13)	C1—C2—C3—C4^v	177.71 (19)
Cd1^iv—O2—C1—O1	113.9 (2)	C3—C2—C4—F2	179.70 (19)
Cd1^iv—O2—C1—C2	−66.1 (2)	C1—C2—C4—F2	1.4 (3)
O1—C1—C2—C4	−41.9 (3)	C3—C2—C4—C3^v	0.6 (3)
O2—C1—C2—C4	138.0 (2)	C1—C2—C4—C3^v	−177.70 (19)
O1—C1—C2—C3	139.9 (2)	C5A—O3—C5—C6	−28.4 (13)
O2—C1—C2—C3	−40.1 (3)	Cd1—O3—C5—C6	76.5 (7)
C4—C2—C3—F1	179.42 (19)	C5—O3—C5A—C6A	23.6 (10)
C1—C2—C3—F1	−2.3 (3)	Cd1—O3—C5A—C6A	−73.7 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3OA···O2ⁱ	0.85 (1)	1.94 (2)	2.719 (2)	152 (4)
O3—H3OB···F2ⁱⁱ	0.85 (1)	2.40 (2)	3.196 (2)	156 (4)

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

Selected bond lengths (Å) top

Cd1—O1	2.2526 (15)	Cd1—O3	2.2929 (18)
Cd1—O2ⁱ	2.3194 (15)

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3OA···O2ⁱⁱ	0.850 (5)	1.94 (2)	2.719 (2)	152 (4)
O3—H3OB···F2ⁱ	0.849 (5)	2.402 (18)	3.196 (2)	156 (4)

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

Acknowledgements

This research was supported by the Ministry of Knowledge Economy (MKE) and the Korea Institute for Advancement in Technology (KIAT) through the Workforce Development Program in Strategic Technology.

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