supplementary materials


is5307 scheme

Acta Cryst. (2014). E70, m3    [ doi:10.1107/S1600536813031887 ]

Poly[bis­([mu]4-2,3,5,6-tetra­fluoro­benzene-1,4-di­carboxyl­ato-[kappa]4O1:O1':O4:O4')bis­(tetra­hydro­furan-[kappa]O)dizinc]

S. B. Choi, Y. H. Jhon, N. Ko and J. K. Yang

Abstract top

The title compound, [Zn2(C8F4O4)2(C4H8O)2]n, has a three-dimensional metal-organic framework structure. The asymmetric unit consists of two ZnII atoms, two tetrahydrofuran ligands, one 2,3,5,6-tetra­fluoro­benzene-1,4-di­carboxyl­ate ligand and two half 2,3,5,6-tetra­fluoro­benzene-1,4-di­carboxyl­ate ligands, which are completed by inversion symmetry. One ZnII atom has a distorted trigonal-bipyramidal coordination geometry, while the other has a distorted octa­hedral geometry. Two independent tetra­hydro­furan ligands are each disordered over two sets of sites with occupancy ratios of 0.48 (4):0.52 (4) and 0.469 (17):0.531 (17).

Comment top

We reported previously a porous metal-organic framework (MOF) composed of iron ions and the same ligand in the title compound (Yoon et al., 2007). In the course of making a new MOF using zinc ion, the title compound was obtained as single crystals in hot tetrahydrofurane (THF). The title compound has a three-dimensional framework of which potential void space is filled with coordinated tetrahydrofuran (THF) molecules. Related crystal structures have been reported (Hulvey et al., 2011; Seidel et al., 2011; Yu et al., 2011; Zheng et al., 2008).

Related literature top

For general background of compounds with metal-organic framework structures, see: Yoon et al. (2007). For related crystal structures, see: Hulvey et al. (2011); Seidel et al. (2011); Yoon et al. (2007); Yu et al. (2011); Zheng et al. (2008).

Experimental top

A mixture of Zn(NO3)2.6H2O (56 mg, 0.19 mmol) and tetrafluoroterephthalic acid (15 mg, 0.063 mmol) was added to tetrahydrofuran (5.0 mL) in a Teflon-lined stainless steel autoclave. The mixture was heated at 85 °C for 24 h. Colorless needle crystals were collected and washed with neat N,N-dimethylformamide.

Refinement top

Two THF molecules are statistically disordered over two sites, and their site occupancy factors were refined. Same distance and isotropic behaviour restraints (SADI and ISOR, respectively) were applied for the disordered molecules. H atoms were positions with idealized geometry (C—H = 0.99 Å) and allowed to ride with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] Fig. 1. The coordination environment of the title compound is shown with the atomic numbering scheme. Displacement ellipsoids are drawn at 50% probability level. The atoms with the symmetry codes, (iii) and (iv) are not completely labeled for simplicity. [Symmetry codes: (i) 1 –x, –y, –z; (ii) 2 –x, –y, –z; (iii) 1/2 + x, 1/2 – y, 1/2 + z; (iv) 3/2 – x, 1/2 + y, 1/2 – z.]
[Figure 2] Fig. 2. (left) A projection view along the a axis. (right) For comparison, a same packing diagram is displayed without THF molecules and F atoms.
[Figure 3] Fig. 3. (left) A projection view along the b axis. (right) For comparison, a same packing diagram is displayed without THF molecules and F atoms.
Poly[bis(µ4-2,3,5,6-tetrafluorobenzene-1,4-dicarboxylato-κ4O1:O1':O4:O4')bis(tetrahydrofuran-κO)dizinc] top
Crystal data top
[Zn2(C8F4O4)2(C4H8O)2]F(000) = 1488
Mr = 747.11Dx = 1.919 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2025 reflections
a = 11.9339 (8) Åθ = 2.3–27.0°
b = 12.4369 (9) ŵ = 1.97 mm1
c = 17.9627 (12) ÅT = 173 K
β = 104.051 (1)°Needle, colorless
V = 2586.3 (3) Å30.10 × 0.05 × 0.05 mm
Z = 4
Data collection top
SMART APEX CCD
diffractometer
5980 independent reflections
Radiation source: fine-focus sealed tube2859 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.111
phi and ω scansθmax = 27.9°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1514
Tmin = 0.827, Tmax = 0.908k = 1613
16096 measured reflectionsl = 2323
Refinement top
Refinement on F281 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.0519P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139(Δ/σ)max < 0.001
S = 0.94Δρmax = 0.66 e Å3
5980 reflectionsΔρmin = 0.78 e Å3
444 parameters
Crystal data top
[Zn2(C8F4O4)2(C4H8O)2]V = 2586.3 (3) Å3
Mr = 747.11Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.9339 (8) ŵ = 1.97 mm1
b = 12.4369 (9) ÅT = 173 K
c = 17.9627 (12) Å0.10 × 0.05 × 0.05 mm
β = 104.051 (1)°
Data collection top
SMART APEX CCD
diffractometer
5980 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2859 reflections with I > 2σ(I)
Tmin = 0.827, Tmax = 0.908Rint = 0.111
16096 measured reflectionsθmax = 27.9°
Refinement top
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.139Δρmax = 0.66 e Å3
S = 0.94Δρmin = 0.78 e Å3
5980 reflectionsAbsolute structure: ?
444 parametersAbsolute structure parameter: ?
81 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Zn10.95391 (6)0.25834 (6)0.23174 (4)0.0190 (2)
Zn20.74360 (6)0.06295 (6)0.22126 (4)0.0197 (2)
F10.7946 (3)0.3132 (4)0.0193 (2)0.0360 (11)
F20.6468 (3)0.3797 (4)0.14747 (19)0.0380 (11)
F30.3476 (3)0.3893 (3)0.0176 (2)0.0343 (10)
F40.4890 (3)0.3084 (3)0.1070 (2)0.0350 (11)
F50.3829 (3)0.0673 (3)0.10356 (19)0.0319 (10)
F60.3318 (3)0.1509 (3)0.0385 (2)0.0314 (10)
F71.1600 (3)0.0283 (3)0.1343 (2)0.0380 (11)
F81.2137 (3)0.0770 (3)0.0024 (2)0.0363 (11)
O10.6808 (4)0.1774 (4)0.1436 (2)0.0294 (12)
O20.8233 (3)0.2972 (4)0.1440 (2)0.0231 (11)
O30.3584 (4)0.5058 (4)0.1657 (2)0.0315 (12)
O40.3716 (3)0.3404 (4)0.2065 (2)0.0211 (10)
O50.6454 (3)0.0690 (4)0.2015 (2)0.0236 (11)
O60.4829 (3)0.1595 (4)0.1690 (2)0.0217 (10)
O70.8535 (4)0.0103 (4)0.1569 (2)0.0308 (12)
O81.0048 (4)0.1237 (4)0.1836 (2)0.0264 (11)
C10.6473 (5)0.3081 (5)0.0487 (3)0.0188 (14)
C20.6838 (5)0.3309 (6)0.0176 (3)0.0222 (16)
C30.6081 (5)0.3672 (5)0.0829 (3)0.0223 (15)
C40.4933 (5)0.3872 (5)0.0855 (3)0.0215 (15)
C50.4593 (5)0.3698 (5)0.0191 (4)0.0209 (15)
C60.5307 (5)0.3282 (5)0.0456 (3)0.0208 (15)
C70.7248 (5)0.2574 (6)0.1181 (3)0.0203 (15)
C80.4033 (6)0.4161 (5)0.1576 (4)0.0224 (16)
C90.5536 (5)0.0941 (5)0.1541 (3)0.0187 (15)
C100.5264 (5)0.0450 (5)0.0742 (3)0.0197 (15)
C110.4409 (5)0.0323 (5)0.0528 (3)0.0195 (15)
C120.4157 (5)0.0753 (5)0.0206 (3)0.0171 (14)
C130.9406 (6)0.0548 (6)0.1450 (4)0.0255 (16)
C140.9707 (6)0.0254 (5)0.0699 (4)0.0233 (16)
C151.0804 (5)0.0119 (6)0.0676 (3)0.0236 (16)
C161.1077 (6)0.0371 (6)0.0006 (4)0.0256 (16)
O90.6305 (4)0.1245 (4)0.2867 (3)0.0305 (12)
O101.0752 (4)0.3383 (4)0.1859 (2)0.0315 (12)
C170.5732 (8)0.0626 (7)0.3327 (5)0.062 (3)
H17A0.62410.00390.35850.075*0.48 (4)
H17B0.50200.03040.30040.075*0.48 (4)
H17C0.62990.03160.37710.075*0.52 (4)
H17D0.52940.00310.30230.075*0.52 (4)
C180.544 (3)0.1357 (7)0.3906 (13)0.046 (8)0.48 (4)
H18A0.60240.12970.44010.055*0.48 (4)
H18B0.46730.11780.39900.055*0.48 (4)
C210.4935 (15)0.1368 (7)0.3593 (17)0.044 (6)0.52 (4)
H21A0.48790.11750.41170.053*0.52 (4)
H21B0.41530.13380.32450.053*0.52 (4)
C190.5440 (8)0.2459 (7)0.3585 (5)0.065 (3)
H19A0.57960.29760.39930.078*0.48 (4)
H19B0.46410.26960.33480.078*0.48 (4)
H19C0.59390.26430.40950.078*0.52 (4)
H19D0.48260.30090.34400.078*0.52 (4)
C200.6139 (7)0.2383 (6)0.2990 (5)0.046 (2)
H20A0.57220.27300.25060.055*
H20B0.68940.27460.31750.055*
C221.0721 (13)0.337 (3)0.1044 (4)0.036 (13)0.531 (17)
H22A1.01100.38580.07570.044*0.531 (17)
H22B1.05710.26370.08320.044*0.531 (17)
C231.1889 (11)0.3754 (18)0.0989 (8)0.059 (6)0.531 (17)
H23A1.21770.33130.06150.071*0.531 (17)
H23B1.18540.45140.08220.071*0.531 (17)
C241.2664 (13)0.3637 (18)0.1776 (7)0.057 (6)0.531 (17)
H24A1.30070.43400.19640.069*0.531 (17)
H24B1.32980.31270.17670.069*0.531 (17)
C251.1943 (7)0.3222 (17)0.2292 (8)0.044 (5)0.531 (17)
H25A1.20990.24500.24080.053*0.531 (17)
H25B1.21020.36290.27800.053*0.531 (17)
C261.1923 (7)0.3668 (15)0.2270 (8)0.028 (5)0.469 (17)
H26A1.20820.34720.28200.034*0.469 (17)
H26B1.20850.44410.22190.034*0.469 (17)
C271.2578 (19)0.297 (2)0.1839 (9)0.085 (8)0.469 (17)
H27A1.33430.32950.18620.102*0.469 (17)
H27B1.27020.22530.20820.102*0.469 (17)
C281.1923 (13)0.2859 (18)0.1020 (9)0.050 (6)0.469 (17)
H28A1.18900.21000.08490.060*0.469 (17)
H28B1.22650.33050.06750.060*0.469 (17)
C291.0754 (15)0.326 (3)0.1053 (5)0.046 (18)0.469 (17)
H29A1.05970.39650.07860.056*0.469 (17)
H29B1.01490.27490.07990.056*0.469 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0188 (4)0.0257 (5)0.0107 (3)0.0033 (3)0.0004 (3)0.0011 (4)
Zn20.0196 (4)0.0255 (5)0.0122 (4)0.0005 (4)0.0004 (3)0.0040 (4)
F10.017 (2)0.068 (3)0.022 (2)0.012 (2)0.0021 (17)0.008 (2)
F20.034 (2)0.067 (3)0.0146 (19)0.015 (2)0.0089 (18)0.004 (2)
F30.017 (2)0.058 (3)0.026 (2)0.006 (2)0.0027 (17)0.009 (2)
F40.026 (2)0.061 (3)0.018 (2)0.012 (2)0.0071 (18)0.003 (2)
F50.035 (2)0.047 (3)0.0158 (18)0.0017 (19)0.0109 (17)0.012 (2)
F60.038 (2)0.034 (3)0.021 (2)0.0058 (18)0.0038 (18)0.0145 (19)
F70.033 (2)0.059 (3)0.019 (2)0.002 (2)0.0005 (18)0.010 (2)
F80.022 (2)0.057 (3)0.029 (2)0.005 (2)0.0049 (18)0.009 (2)
O10.022 (3)0.036 (3)0.025 (3)0.007 (2)0.003 (2)0.006 (2)
O20.019 (2)0.031 (3)0.013 (2)0.003 (2)0.0070 (19)0.002 (2)
O30.041 (3)0.026 (3)0.023 (3)0.001 (2)0.001 (2)0.008 (2)
O40.021 (2)0.030 (3)0.011 (2)0.002 (2)0.0017 (19)0.001 (2)
O50.025 (2)0.027 (3)0.013 (2)0.003 (2)0.0051 (19)0.007 (2)
O60.023 (2)0.026 (3)0.016 (2)0.006 (2)0.0026 (19)0.005 (2)
O70.032 (3)0.039 (3)0.026 (3)0.010 (2)0.016 (2)0.012 (2)
O80.025 (3)0.032 (3)0.022 (2)0.014 (2)0.007 (2)0.005 (2)
C10.018 (3)0.025 (4)0.012 (3)0.001 (3)0.000 (3)0.001 (3)
C20.018 (3)0.033 (4)0.013 (3)0.002 (3)0.001 (3)0.000 (3)
C30.026 (4)0.028 (4)0.011 (3)0.002 (3)0.003 (3)0.006 (3)
C40.025 (4)0.023 (4)0.016 (3)0.004 (3)0.003 (3)0.005 (3)
C50.017 (3)0.023 (4)0.020 (3)0.002 (3)0.000 (3)0.004 (3)
C60.018 (3)0.032 (4)0.010 (3)0.002 (3)0.003 (3)0.001 (3)
C70.019 (3)0.029 (4)0.012 (3)0.002 (3)0.003 (3)0.004 (3)
C80.030 (4)0.019 (4)0.017 (3)0.005 (3)0.003 (3)0.003 (3)
C90.025 (4)0.016 (4)0.013 (3)0.000 (3)0.001 (3)0.000 (3)
C100.017 (3)0.026 (4)0.014 (3)0.001 (3)0.000 (3)0.002 (3)
C110.022 (3)0.021 (4)0.014 (3)0.000 (3)0.003 (3)0.003 (3)
C120.013 (3)0.019 (4)0.016 (3)0.002 (3)0.002 (3)0.004 (3)
C130.031 (4)0.025 (4)0.023 (4)0.005 (3)0.012 (3)0.001 (3)
C140.028 (4)0.021 (4)0.020 (3)0.003 (3)0.006 (3)0.001 (3)
C150.024 (4)0.028 (4)0.016 (3)0.001 (3)0.001 (3)0.002 (3)
C160.025 (4)0.031 (5)0.022 (4)0.006 (3)0.007 (3)0.003 (3)
O90.031 (3)0.026 (3)0.040 (3)0.002 (2)0.019 (2)0.002 (2)
O100.024 (3)0.045 (3)0.025 (3)0.010 (2)0.007 (2)0.009 (2)
C170.078 (7)0.047 (6)0.084 (7)0.001 (5)0.061 (6)0.003 (5)
C180.062 (18)0.048 (13)0.038 (12)0.003 (9)0.031 (13)0.006 (10)
C210.045 (6)0.045 (6)0.045 (6)0.001 (2)0.012 (2)0.001 (2)
C190.086 (7)0.050 (7)0.073 (6)0.008 (6)0.046 (6)0.003 (6)
C200.059 (5)0.030 (5)0.055 (5)0.003 (4)0.026 (4)0.008 (4)
C220.037 (13)0.037 (13)0.036 (13)0.000 (2)0.011 (4)0.001 (2)
C230.059 (6)0.061 (6)0.059 (6)0.001 (2)0.017 (2)0.001 (2)
C240.056 (6)0.059 (6)0.058 (6)0.002 (2)0.016 (2)0.000 (2)
C250.043 (5)0.045 (5)0.044 (5)0.000 (2)0.011 (2)0.001 (2)
C260.027 (5)0.028 (5)0.029 (5)0.000 (2)0.007 (2)0.001 (2)
C270.084 (9)0.085 (9)0.085 (9)0.001 (2)0.021 (3)0.001 (2)
C280.050 (6)0.051 (6)0.050 (6)0.001 (2)0.014 (2)0.001 (2)
C290.047 (18)0.047 (18)0.046 (18)0.000 (2)0.013 (5)0.001 (2)
Geometric parameters (Å, º) top
Zn1—O21.988 (4)O9—C201.454 (8)
Zn1—O6i2.034 (4)O10—C221.455 (6)
Zn1—O82.043 (4)O10—C291.456 (6)
Zn1—O4ii2.058 (4)O10—C261.457 (6)
Zn1—O102.084 (4)O10—C251.459 (6)
Zn2—O51.998 (4)C17—C181.484 (9)
Zn2—O12.007 (5)C17—C211.485 (9)
Zn2—O72.055 (4)C17—H17A0.9900
Zn2—O4ii2.122 (4)C17—H17B0.9900
Zn2—O92.136 (4)C17—H17C0.9900
Zn2—O3ii2.319 (4)C17—H17D0.9900
F1—C21.348 (7)C18—C191.487 (9)
F2—C31.357 (7)C18—H18A0.9900
F3—C51.362 (7)C18—H18B0.9900
F4—C61.338 (7)C21—C191.485 (9)
F5—C111.344 (7)C21—H21A0.9900
F6—C121.354 (7)C21—H21B0.9900
F7—C151.352 (6)C19—C201.511 (10)
F8—C161.352 (7)C19—H19A0.9900
O1—C71.262 (7)C19—H19B0.9900
O2—C71.256 (7)C19—H19C0.9900
O3—C81.231 (7)C19—H19D0.9900
O4—C81.280 (7)C20—H20A0.9900
O5—C91.253 (7)C20—H20B0.9900
O6—C91.246 (7)C22—C231.498 (8)
O7—C131.241 (7)C22—H22A0.9900
O8—C131.243 (7)C22—H22B0.9900
C1—C21.393 (8)C23—C241.497 (8)
C1—C61.402 (8)C23—H23A0.9900
C1—C71.499 (8)C23—H23B0.9900
C2—C31.372 (8)C24—C251.501 (8)
C3—C41.382 (8)C24—H24A0.9900
C4—C51.366 (8)C24—H24B0.9900
C4—C81.512 (8)C25—H25A0.9900
C5—C61.365 (8)C25—H25B0.9900
C9—C101.521 (8)C26—C271.501 (8)
C10—C12iii1.365 (8)C26—H26A0.9900
C10—C111.387 (8)C26—H26B0.9900
C11—C121.388 (8)C27—C281.496 (8)
C12—C10iii1.365 (8)C27—H27A0.9900
C13—C141.522 (8)C27—H27B0.9900
C14—C16iv1.388 (8)C28—C291.498 (8)
C14—C151.398 (8)C28—H28A0.9900
C15—C161.358 (8)C28—H28B0.9900
C16—C14iv1.388 (8)C29—H29A0.9900
O9—C171.420 (9)C29—H29B0.9900
O2—Zn1—O6i128.65 (18)C25—O10—Zn1113.8 (6)
O2—Zn1—O896.92 (18)O9—C17—C18107.7 (8)
O6i—Zn1—O8134.23 (17)O9—C17—C21106.6 (9)
O2—Zn1—O4ii100.81 (17)O9—C17—H17A110.2
O6i—Zn1—O4ii87.19 (16)C18—C17—H17A110.2
O8—Zn1—O4ii88.21 (18)O9—C17—H17B110.2
O2—Zn1—O1093.25 (17)C18—C17—H17B110.2
O6i—Zn1—O1087.80 (17)H17A—C17—H17B108.5
O8—Zn1—O1085.27 (18)O9—C17—H17C110.4
O4ii—Zn1—O10165.12 (17)C21—C17—H17C110.4
O5—Zn2—O1110.81 (17)O9—C17—H17D110.4
O5—Zn2—O793.75 (18)C21—C17—H17D110.4
O1—Zn2—O790.97 (19)H17C—C17—H17D108.6
O5—Zn2—O4ii151.45 (16)C17—C18—C19105.7 (9)
O1—Zn2—O4ii96.62 (18)C17—C18—H18A110.6
O7—Zn2—O4ii93.52 (16)C19—C18—H18A110.6
O5—Zn2—O988.31 (18)C17—C18—H18B110.6
O1—Zn2—O987.05 (18)C19—C18—H18B110.6
O7—Zn2—O9177.55 (19)H18A—C18—H18B108.7
O4ii—Zn2—O985.28 (16)C17—C21—C19105.8 (9)
O5—Zn2—O3ii92.81 (16)C17—C21—H21A110.6
O1—Zn2—O3ii155.73 (18)C19—C21—H21A110.6
O7—Zn2—O3ii93.03 (17)C17—C21—H21B110.6
O4ii—Zn2—O3ii59.25 (17)C19—C21—H21B110.6
O9—Zn2—O3ii88.19 (17)H21A—C21—H21B108.7
C7—O1—Zn2133.9 (4)C21—C19—C20104.2 (9)
C7—O2—Zn1132.9 (4)C18—C19—C20105.5 (8)
C8—O3—Zn2v85.2 (4)C18—C19—H19A110.6
C8—O4—Zn1v135.1 (4)C20—C19—H19A110.6
C8—O4—Zn2v92.9 (4)C18—C19—H19B110.6
Zn1v—O4—Zn2v112.04 (18)C20—C19—H19B110.6
C9—O5—Zn2134.8 (4)H19A—C19—H19B108.8
C9—O6—Zn1vi113.0 (4)C21—C19—H19C110.9
C13—O7—Zn2129.1 (4)C20—C19—H19C110.9
C13—O8—Zn1126.5 (4)C21—C19—H19D110.9
C2—C1—C6116.3 (5)C20—C19—H19D110.9
C2—C1—C7122.6 (5)H19C—C19—H19D108.9
C6—C1—C7120.9 (5)O9—C20—C19106.7 (6)
F1—C2—C3118.8 (5)O9—C20—H20A110.4
F1—C2—C1119.8 (5)C19—C20—H20A110.4
C3—C2—C1121.3 (6)O9—C20—H20B110.4
F2—C3—C2118.5 (6)C19—C20—H20B110.4
F2—C3—C4119.4 (5)H20A—C20—H20B108.6
C2—C3—C4122.0 (6)O10—C22—C23105.5 (10)
C5—C4—C3116.4 (6)O10—C22—H22A110.6
C5—C4—C8119.1 (5)C23—C22—H22A110.6
C3—C4—C8124.3 (6)O10—C22—H22B110.6
F3—C5—C4119.2 (5)C23—C22—H22B110.6
F3—C5—C6117.5 (6)H22A—C22—H22B108.8
C4—C5—C6123.1 (6)C24—C23—C22106.1 (12)
F4—C6—C5119.4 (5)C24—C23—H23A110.5
F4—C6—C1119.9 (5)C22—C23—H23A110.5
C5—C6—C1120.6 (6)C24—C23—H23B110.5
O2—C7—O1127.7 (6)C22—C23—H23B110.5
O2—C7—C1118.4 (6)H23A—C23—H23B108.7
O1—C7—C1114.0 (5)C23—C24—C25107.5 (11)
O3—C8—O4122.6 (6)C23—C24—H24A110.2
O3—C8—C4121.0 (6)C25—C24—H24A110.2
O4—C8—C4116.2 (6)C23—C24—H24B110.2
O6—C9—O5122.8 (5)C25—C24—H24B110.2
O6—C9—C10117.7 (5)H24A—C24—H24B108.5
O5—C9—C10119.5 (6)O10—C25—C24104.7 (9)
C12iii—C10—C11117.4 (6)O10—C25—H25A110.8
C12iii—C10—C9121.7 (6)C24—C25—H25A110.8
C11—C10—C9120.8 (6)O10—C25—H25B110.8
F5—C11—C12119.5 (5)C24—C25—H25B110.8
F5—C11—C10120.2 (5)H25A—C25—H25B108.9
C12—C11—C10120.3 (6)O10—C26—C2798.8 (11)
F6—C12—C10iii119.7 (5)O10—C26—H26A112.0
F6—C12—C11118.1 (5)C27—C26—H26A112.0
C10iii—C12—C11122.2 (6)O10—C26—H26B112.0
O7—C13—O8129.8 (6)C27—C26—H26B112.0
O7—C13—C14115.7 (6)H26A—C26—H26B109.7
O8—C13—C14114.5 (6)C28—C27—C26110.3 (14)
C16iv—C14—C15115.9 (6)C28—C27—H27A109.6
C16iv—C14—C13122.1 (6)C26—C27—H27A109.6
C15—C14—C13122.0 (6)C28—C27—H27B109.6
F7—C15—C16118.8 (6)C26—C27—H27B109.6
F7—C15—C14119.0 (6)H27A—C27—H27B108.1
C16—C15—C14122.1 (6)C27—C28—C29101.5 (14)
F8—C16—C15119.3 (6)C27—C28—H28A111.5
F8—C16—C14iv118.7 (6)C29—C28—H28A111.5
C15—C16—C14iv122.0 (6)C27—C28—H28B111.5
C17—O9—C20109.7 (5)C29—C28—H28B111.5
C17—O9—Zn2125.7 (4)H28A—C28—H28B109.3
C20—O9—Zn2124.1 (4)O10—C29—C28107.4 (11)
C29—O10—C26107.2 (11)O10—C29—H29A110.2
C22—O10—C25108.6 (9)C28—C29—H29A110.2
C22—O10—Zn1122.9 (8)O10—C29—H29B110.2
C29—O10—Zn1120.9 (12)C28—C29—H29B110.2
C26—O10—Zn1126.0 (8)H29A—C29—H29B108.5
C6—C1—C2—F1179.6 (6)F5—C11—C12—C10iii178.3 (6)
C7—C1—C2—F14.0 (10)C10—C11—C12—C10iii0.6 (11)
C6—C1—C2—C32.3 (10)Zn2—O7—C13—O823.7 (11)
C7—C1—C2—C3173.3 (6)Zn2—O7—C13—C14152.8 (4)
F1—C2—C3—F22.6 (10)Zn1—O8—C13—O745.1 (11)
C1—C2—C3—F2174.8 (6)Zn1—O8—C13—C14131.4 (5)
F1—C2—C3—C4180.0 (6)O7—C13—C14—C16iv55.4 (9)
C1—C2—C3—C42.7 (11)O8—C13—C14—C16iv121.6 (7)
F2—C3—C4—C5178.0 (6)O7—C13—C14—C15126.7 (7)
C2—C3—C4—C50.6 (10)O8—C13—C14—C1556.2 (9)
F2—C3—C4—C84.0 (10)C16iv—C14—C15—F7178.0 (6)
C2—C3—C4—C8173.4 (6)C13—C14—C15—F74.0 (10)
C3—C4—C5—F3179.2 (6)C16iv—C14—C15—C161.4 (11)
C8—C4—C5—F36.4 (10)C13—C14—C15—C16179.3 (7)
C3—C4—C5—C64.3 (10)F7—C15—C16—F80.6 (10)
C8—C4—C5—C6170.0 (6)C14—C15—C16—F8177.3 (6)
F3—C5—C6—F40.0 (9)F7—C15—C16—C14iv178.1 (6)
C4—C5—C6—F4176.5 (6)C14—C15—C16—C14iv1.4 (12)
F3—C5—C6—C1178.7 (6)C20—O9—C17—C1814.5 (17)
C4—C5—C6—C14.8 (11)Zn2—O9—C17—C18157.5 (15)
C2—C1—C6—F4180.0 (6)C20—O9—C17—C2114.8 (14)
C7—C1—C6—F44.3 (10)Zn2—O9—C17—C21173.2 (11)
C2—C1—C6—C51.3 (10)O9—C17—C18—C1922 (3)
C7—C1—C6—C5177.0 (6)C21—C17—C18—C1970.7 (8)
Zn1—O2—C7—O10.7 (10)O9—C17—C21—C1926 (2)
Zn1—O2—C7—C1179.3 (4)C18—C17—C21—C1970.9 (8)
Zn2—O1—C7—O211.3 (11)C17—C21—C19—C1870.7 (8)
Zn2—O1—C7—C1168.7 (4)C17—C21—C19—C2026 (2)
C2—C1—C7—O249.9 (9)C17—C18—C19—C2170.8 (8)
C6—C1—C7—O2134.7 (7)C17—C18—C19—C2020 (3)
C2—C1—C7—O1130.1 (7)C17—O9—C20—C191.6 (9)
C6—C1—C7—O145.3 (9)Zn2—O9—C20—C19170.6 (5)
Zn2v—O3—C8—O40.1 (6)C21—C19—C20—O917.1 (14)
Zn2v—O3—C8—C4175.0 (6)C18—C19—C20—O911.8 (17)
Zn1v—O4—C8—O3125.7 (6)C29—O10—C22—C2394 (13)
Zn2v—O4—C8—O30.1 (7)C26—O10—C22—C235 (2)
Zn1v—O4—C8—C459.0 (8)C25—O10—C22—C2328 (3)
Zn2v—O4—C8—C4175.3 (5)Zn1—O10—C22—C23164.3 (13)
Zn1v—O4—C8—Zn2v125.8 (5)O10—C22—C23—C2418 (3)
C5—C4—C8—O373.2 (9)C22—C23—C24—C252 (2)
C3—C4—C8—O3113.0 (8)C22—O10—C25—C2427 (2)
C5—C4—C8—O4102.3 (7)C29—O10—C25—C2432 (2)
C3—C4—C8—O471.6 (9)C26—O10—C25—C2464 (2)
Zn1vi—O6—C9—O511.4 (8)Zn1—O10—C25—C24167.3 (13)
Zn1vi—O6—C9—C10167.6 (4)C23—C24—C25—O1015 (2)
Zn2—O5—C9—O6149.5 (5)C22—O10—C26—C2744 (2)
Zn2—O5—C9—C1031.5 (9)C29—O10—C26—C2738 (2)
O6—C9—C10—C12iii106.3 (7)C25—O10—C26—C2753 (2)
O5—C9—C10—C12iii72.7 (8)Zn1—O10—C26—C27114.9 (15)
O6—C9—C10—C1173.4 (8)O10—C26—C27—C2832 (3)
O5—C9—C10—C11107.6 (7)C26—C27—C28—C2914 (3)
C12iii—C10—C11—F5178.4 (6)C22—O10—C29—C28124 (15)
C9—C10—C11—F52.0 (9)C26—O10—C29—C2832 (3)
C12iii—C10—C11—C120.6 (10)C25—O10—C29—C289 (3)
C9—C10—C11—C12179.1 (6)Zn1—O10—C29—C28122.8 (17)
F5—C11—C12—F60.7 (9)C27—C28—C29—O1010 (3)
C10—C11—C12—F6179.7 (5)
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+2, y, z; (v) x1/2, y+1/2, z1/2; (vi) x+3/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Zn2(C8F4O4)2(C4H8O)2]
Mr747.11
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)11.9339 (8), 12.4369 (9), 17.9627 (12)
β (°) 104.051 (1)
V3)2586.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.97
Crystal size (mm)0.10 × 0.05 × 0.05
Data collection
DiffractometerSMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.827, 0.908
No. of measured, independent and
observed [I > 2σ(I)] reflections
16096, 5980, 2859
Rint0.111
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.139, 0.94
No. of reflections5980
No. of parameters444
No. of restraints81
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.66, 0.78

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Acknowledgements top

This research was supported by the Energy Efficiency & Resources of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant funded by the Korean Government Ministry of Knowledge Economy (No. 20122010100120).

references
References top

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Hulvey, Z., Sava, D. A., Eckert, J. & Cheetham, A. K. (2011). Inorg. Chem. 50, 403–405.

Seidel, C., Ahlers, R. & Ruschewitz, U. (2011). Cryst. Growth Des. 11, 5053–5063.

Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Yoon, J. H., Choi, S. B., Oh, Y. J., Seo, M. J., Jhon, Y. H., Lee, T.-B., Kim, D., Choi, S. H. & Kim, J. (2007). Catal. Today, 120, 324–329.

Yu, J., Zhang, Y.-F., Sun, F.-A. & Chen, Q. (2011). Acta Cryst. E67, m527–m528.

Zheng, C.-G., Hong, J.-Q., Zhang, J. & Wang, C. (2008). Acta Cryst. E64, m879.