metal-organic compounds
Poly[bis(μ4-2,3,5,6-tetrafluorobenzene-1,4-dicarboxylato-κ4O1:O1′:O4:O4′)bis(tetrahydrofuran-κO)dizinc]
aDepartment of Chemistry, Soongsil University, 369 Sangdo-Ro, Dongjak-Gu, Seoul 156-743, Republic of Korea
*Correspondence e-mail: jinkukyang@ssu.ac.kr
The title compound, [Zn2(C8F4O4)2(C4H8O)2]n, has a three-dimensional metal-organic framework structure. The 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).
CCDC reference: 973266
Related literature
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
Crystal data
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Data collection: SMART (Bruker, 2007); cell 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: 973266
https://doi.org/10.1107/S1600536813031887/is5307sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813031887/is5307Isup2.hkl
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.
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).
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).
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).
Data collection: SMART (Bruker, 2007); cell
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).[Zn2(C8F4O4)2(C4H8O)2] | F(000) = 1488 |
Mr = 747.11 | Dx = 1.919 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2025 reflections |
a = 11.9339 (8) Å | θ = 2.3–27.0° |
b = 12.4369 (9) Å | µ = 1.97 mm−1 |
c = 17.9627 (12) Å | T = 173 K |
β = 104.051 (1)° | Needle, colorless |
V = 2586.3 (3) Å3 | 0.10 × 0.05 × 0.05 mm |
Z = 4 |
SMART APEX CCD diffractometer | 5980 independent reflections |
Radiation source: fine-focus sealed tube | 2859 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.111 |
phi and ω scans | θmax = 27.9°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −15→14 |
Tmin = 0.827, Tmax = 0.908 | k = −16→13 |
16096 measured reflections | l = −23→23 |
Refinement on F2 | 81 restraints |
Least-squares matrix: full | H-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 = 0.94 | Δρmax = 0.66 e Å−3 |
5980 reflections | Δρmin = −0.78 e Å−3 |
444 parameters |
[Zn2(C8F4O4)2(C4H8O)2] | V = 2586.3 (3) Å3 |
Mr = 747.11 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.9339 (8) Å | µ = 1.97 mm−1 |
b = 12.4369 (9) Å | T = 173 K |
c = 17.9627 (12) Å | 0.10 × 0.05 × 0.05 mm |
β = 104.051 (1)° |
SMART APEX CCD diffractometer | 5980 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2859 reflections with I > 2σ(I) |
Tmin = 0.827, Tmax = 0.908 | Rint = 0.111 |
16096 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 81 restraints |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.66 e Å−3 |
5980 reflections | Δρmin = −0.78 e Å−3 |
444 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.95391 (6) | 0.25834 (6) | 0.23174 (4) | 0.0190 (2) | |
Zn2 | 0.74360 (6) | 0.06295 (6) | 0.22126 (4) | 0.0197 (2) | |
F1 | 0.7946 (3) | 0.3132 (4) | −0.0193 (2) | 0.0360 (11) | |
F2 | 0.6468 (3) | 0.3797 (4) | −0.14747 (19) | 0.0380 (11) | |
F3 | 0.3476 (3) | 0.3893 (3) | −0.0176 (2) | 0.0343 (10) | |
F4 | 0.4890 (3) | 0.3084 (3) | 0.1070 (2) | 0.0350 (11) | |
F5 | 0.3829 (3) | 0.0673 (3) | 0.10356 (19) | 0.0319 (10) | |
F6 | 0.3318 (3) | 0.1509 (3) | −0.0385 (2) | 0.0314 (10) | |
F7 | 1.1600 (3) | −0.0283 (3) | 0.1343 (2) | 0.0380 (11) | |
F8 | 1.2137 (3) | −0.0770 (3) | 0.0024 (2) | 0.0363 (11) | |
O1 | 0.6808 (4) | 0.1774 (4) | 0.1436 (2) | 0.0294 (12) | |
O2 | 0.8233 (3) | 0.2972 (4) | 0.1440 (2) | 0.0231 (11) | |
O3 | 0.3584 (4) | 0.5058 (4) | −0.1657 (2) | 0.0315 (12) | |
O4 | 0.3716 (3) | 0.3404 (4) | −0.2065 (2) | 0.0211 (10) | |
O5 | 0.6454 (3) | −0.0690 (4) | 0.2015 (2) | 0.0236 (11) | |
O6 | 0.4829 (3) | −0.1595 (4) | 0.1690 (2) | 0.0217 (10) | |
O7 | 0.8535 (4) | 0.0103 (4) | 0.1569 (2) | 0.0308 (12) | |
O8 | 1.0048 (4) | 0.1237 (4) | 0.1836 (2) | 0.0264 (11) | |
C1 | 0.6473 (5) | 0.3081 (5) | 0.0487 (3) | 0.0188 (14) | |
C2 | 0.6838 (5) | 0.3309 (6) | −0.0176 (3) | 0.0222 (16) | |
C3 | 0.6081 (5) | 0.3672 (5) | −0.0829 (3) | 0.0223 (15) | |
C4 | 0.4933 (5) | 0.3872 (5) | −0.0855 (3) | 0.0215 (15) | |
C5 | 0.4593 (5) | 0.3698 (5) | −0.0191 (4) | 0.0209 (15) | |
C6 | 0.5307 (5) | 0.3282 (5) | 0.0456 (3) | 0.0208 (15) | |
C7 | 0.7248 (5) | 0.2574 (6) | 0.1181 (3) | 0.0203 (15) | |
C8 | 0.4033 (6) | 0.4161 (5) | −0.1576 (4) | 0.0224 (16) | |
C9 | 0.5536 (5) | −0.0941 (5) | 0.1541 (3) | 0.0187 (15) | |
C10 | 0.5264 (5) | −0.0450 (5) | 0.0742 (3) | 0.0197 (15) | |
C11 | 0.4409 (5) | 0.0323 (5) | 0.0528 (3) | 0.0195 (15) | |
C12 | 0.4157 (5) | 0.0753 (5) | −0.0206 (3) | 0.0171 (14) | |
C13 | 0.9406 (6) | 0.0548 (6) | 0.1450 (4) | 0.0255 (16) | |
C14 | 0.9707 (6) | 0.0254 (5) | 0.0699 (4) | 0.0233 (16) | |
C15 | 1.0804 (5) | −0.0119 (6) | 0.0676 (3) | 0.0236 (16) | |
C16 | 1.1077 (6) | −0.0371 (6) | 0.0006 (4) | 0.0256 (16) | |
O9 | 0.6305 (4) | 0.1245 (4) | 0.2867 (3) | 0.0305 (12) | |
O10 | 1.0752 (4) | 0.3383 (4) | 0.1859 (2) | 0.0315 (12) | |
C17 | 0.5732 (8) | 0.0626 (7) | 0.3327 (5) | 0.062 (3) | |
H17A | 0.6241 | 0.0039 | 0.3585 | 0.075* | 0.48 (4) |
H17B | 0.5020 | 0.0304 | 0.3004 | 0.075* | 0.48 (4) |
H17C | 0.6299 | 0.0316 | 0.3771 | 0.075* | 0.52 (4) |
H17D | 0.5294 | 0.0031 | 0.3023 | 0.075* | 0.52 (4) |
C18 | 0.544 (3) | 0.1357 (7) | 0.3906 (13) | 0.046 (8) | 0.48 (4) |
H18A | 0.6024 | 0.1297 | 0.4401 | 0.055* | 0.48 (4) |
H18B | 0.4673 | 0.1178 | 0.3990 | 0.055* | 0.48 (4) |
C21 | 0.4935 (15) | 0.1368 (7) | 0.3593 (17) | 0.044 (6) | 0.52 (4) |
H21A | 0.4879 | 0.1175 | 0.4117 | 0.053* | 0.52 (4) |
H21B | 0.4153 | 0.1338 | 0.3245 | 0.053* | 0.52 (4) |
C19 | 0.5440 (8) | 0.2459 (7) | 0.3585 (5) | 0.065 (3) | |
H19A | 0.5796 | 0.2976 | 0.3993 | 0.078* | 0.48 (4) |
H19B | 0.4641 | 0.2696 | 0.3348 | 0.078* | 0.48 (4) |
H19C | 0.5939 | 0.2643 | 0.4095 | 0.078* | 0.52 (4) |
H19D | 0.4826 | 0.3009 | 0.3440 | 0.078* | 0.52 (4) |
C20 | 0.6139 (7) | 0.2383 (6) | 0.2990 (5) | 0.046 (2) | |
H20A | 0.5722 | 0.2730 | 0.2506 | 0.055* | |
H20B | 0.6894 | 0.2746 | 0.3175 | 0.055* | |
C22 | 1.0721 (13) | 0.337 (3) | 0.1044 (4) | 0.036 (13) | 0.531 (17) |
H22A | 1.0110 | 0.3858 | 0.0757 | 0.044* | 0.531 (17) |
H22B | 1.0571 | 0.2637 | 0.0832 | 0.044* | 0.531 (17) |
C23 | 1.1889 (11) | 0.3754 (18) | 0.0989 (8) | 0.059 (6) | 0.531 (17) |
H23A | 1.2177 | 0.3313 | 0.0615 | 0.071* | 0.531 (17) |
H23B | 1.1854 | 0.4514 | 0.0822 | 0.071* | 0.531 (17) |
C24 | 1.2664 (13) | 0.3637 (18) | 0.1776 (7) | 0.057 (6) | 0.531 (17) |
H24A | 1.3007 | 0.4340 | 0.1964 | 0.069* | 0.531 (17) |
H24B | 1.3298 | 0.3127 | 0.1767 | 0.069* | 0.531 (17) |
C25 | 1.1943 (7) | 0.3222 (17) | 0.2292 (8) | 0.044 (5) | 0.531 (17) |
H25A | 1.2099 | 0.2450 | 0.2408 | 0.053* | 0.531 (17) |
H25B | 1.2102 | 0.3629 | 0.2780 | 0.053* | 0.531 (17) |
C26 | 1.1923 (7) | 0.3668 (15) | 0.2270 (8) | 0.028 (5) | 0.469 (17) |
H26A | 1.2082 | 0.3472 | 0.2820 | 0.034* | 0.469 (17) |
H26B | 1.2085 | 0.4441 | 0.2219 | 0.034* | 0.469 (17) |
C27 | 1.2578 (19) | 0.297 (2) | 0.1839 (9) | 0.085 (8) | 0.469 (17) |
H27A | 1.3343 | 0.3295 | 0.1862 | 0.102* | 0.469 (17) |
H27B | 1.2702 | 0.2253 | 0.2082 | 0.102* | 0.469 (17) |
C28 | 1.1923 (13) | 0.2859 (18) | 0.1020 (9) | 0.050 (6) | 0.469 (17) |
H28A | 1.1890 | 0.2100 | 0.0849 | 0.060* | 0.469 (17) |
H28B | 1.2265 | 0.3305 | 0.0675 | 0.060* | 0.469 (17) |
C29 | 1.0754 (15) | 0.326 (3) | 0.1053 (5) | 0.046 (18) | 0.469 (17) |
H29A | 1.0597 | 0.3965 | 0.0786 | 0.056* | 0.469 (17) |
H29B | 1.0149 | 0.2749 | 0.0799 | 0.056* | 0.469 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0188 (4) | 0.0257 (5) | 0.0107 (3) | −0.0033 (3) | 0.0004 (3) | −0.0011 (4) |
Zn2 | 0.0196 (4) | 0.0255 (5) | 0.0122 (4) | 0.0005 (4) | 0.0004 (3) | −0.0040 (4) |
F1 | 0.017 (2) | 0.068 (3) | 0.022 (2) | 0.012 (2) | 0.0021 (17) | 0.008 (2) |
F2 | 0.034 (2) | 0.067 (3) | 0.0146 (19) | 0.015 (2) | 0.0089 (18) | 0.004 (2) |
F3 | 0.017 (2) | 0.058 (3) | 0.026 (2) | 0.006 (2) | 0.0027 (17) | 0.009 (2) |
F4 | 0.026 (2) | 0.061 (3) | 0.018 (2) | 0.012 (2) | 0.0071 (18) | 0.003 (2) |
F5 | 0.035 (2) | 0.047 (3) | 0.0158 (18) | 0.0017 (19) | 0.0109 (17) | 0.012 (2) |
F6 | 0.038 (2) | 0.034 (3) | 0.021 (2) | 0.0058 (18) | 0.0038 (18) | 0.0145 (19) |
F7 | 0.033 (2) | 0.059 (3) | 0.019 (2) | −0.002 (2) | 0.0005 (18) | 0.010 (2) |
F8 | 0.022 (2) | 0.057 (3) | 0.029 (2) | −0.005 (2) | 0.0049 (18) | 0.009 (2) |
O1 | 0.022 (3) | 0.036 (3) | 0.025 (3) | 0.007 (2) | −0.003 (2) | −0.006 (2) |
O2 | 0.019 (2) | 0.031 (3) | 0.013 (2) | 0.003 (2) | −0.0070 (19) | −0.002 (2) |
O3 | 0.041 (3) | 0.026 (3) | 0.023 (3) | −0.001 (2) | 0.001 (2) | 0.008 (2) |
O4 | 0.021 (2) | 0.030 (3) | 0.011 (2) | 0.002 (2) | 0.0017 (19) | 0.001 (2) |
O5 | 0.025 (2) | 0.027 (3) | 0.013 (2) | 0.003 (2) | −0.0051 (19) | −0.007 (2) |
O6 | 0.023 (2) | 0.026 (3) | 0.016 (2) | 0.006 (2) | 0.0026 (19) | −0.005 (2) |
O7 | 0.032 (3) | 0.039 (3) | 0.026 (3) | −0.010 (2) | 0.016 (2) | −0.012 (2) |
O8 | 0.025 (3) | 0.032 (3) | 0.022 (2) | −0.014 (2) | 0.007 (2) | −0.005 (2) |
C1 | 0.018 (3) | 0.025 (4) | 0.012 (3) | 0.001 (3) | 0.000 (3) | 0.001 (3) |
C2 | 0.018 (3) | 0.033 (4) | 0.013 (3) | −0.002 (3) | 0.001 (3) | 0.000 (3) |
C3 | 0.026 (4) | 0.028 (4) | 0.011 (3) | −0.002 (3) | 0.003 (3) | −0.006 (3) |
C4 | 0.025 (4) | 0.023 (4) | 0.016 (3) | −0.004 (3) | 0.003 (3) | 0.005 (3) |
C5 | 0.017 (3) | 0.023 (4) | 0.020 (3) | −0.002 (3) | 0.000 (3) | 0.004 (3) |
C6 | 0.018 (3) | 0.032 (4) | 0.010 (3) | 0.002 (3) | −0.003 (3) | 0.001 (3) |
C7 | 0.019 (3) | 0.029 (4) | 0.012 (3) | −0.002 (3) | 0.003 (3) | 0.004 (3) |
C8 | 0.030 (4) | 0.019 (4) | 0.017 (3) | −0.005 (3) | 0.003 (3) | −0.003 (3) |
C9 | 0.025 (4) | 0.016 (4) | 0.013 (3) | 0.000 (3) | 0.001 (3) | 0.000 (3) |
C10 | 0.017 (3) | 0.026 (4) | 0.014 (3) | −0.001 (3) | 0.000 (3) | −0.002 (3) |
C11 | 0.022 (3) | 0.021 (4) | 0.014 (3) | 0.000 (3) | 0.003 (3) | 0.003 (3) |
C12 | 0.013 (3) | 0.019 (4) | 0.016 (3) | −0.002 (3) | −0.002 (3) | 0.004 (3) |
C13 | 0.031 (4) | 0.025 (4) | 0.023 (4) | −0.005 (3) | 0.012 (3) | 0.001 (3) |
C14 | 0.028 (4) | 0.021 (4) | 0.020 (3) | −0.003 (3) | 0.006 (3) | 0.001 (3) |
C15 | 0.024 (4) | 0.028 (4) | 0.016 (3) | −0.001 (3) | 0.001 (3) | 0.002 (3) |
C16 | 0.025 (4) | 0.031 (5) | 0.022 (4) | −0.006 (3) | 0.007 (3) | 0.003 (3) |
O9 | 0.031 (3) | 0.026 (3) | 0.040 (3) | −0.002 (2) | 0.019 (2) | −0.002 (2) |
O10 | 0.024 (3) | 0.045 (3) | 0.025 (3) | −0.010 (2) | 0.007 (2) | −0.009 (2) |
C17 | 0.078 (7) | 0.047 (6) | 0.084 (7) | 0.001 (5) | 0.061 (6) | −0.003 (5) |
C18 | 0.062 (18) | 0.048 (13) | 0.038 (12) | 0.003 (9) | 0.031 (13) | −0.006 (10) |
C21 | 0.045 (6) | 0.045 (6) | 0.045 (6) | −0.001 (2) | 0.012 (2) | −0.001 (2) |
C19 | 0.086 (7) | 0.050 (7) | 0.073 (6) | −0.008 (6) | 0.046 (6) | −0.003 (6) |
C20 | 0.059 (5) | 0.030 (5) | 0.055 (5) | −0.003 (4) | 0.026 (4) | 0.008 (4) |
C22 | 0.037 (13) | 0.037 (13) | 0.036 (13) | 0.000 (2) | 0.011 (4) | −0.001 (2) |
C23 | 0.059 (6) | 0.061 (6) | 0.059 (6) | 0.001 (2) | 0.017 (2) | −0.001 (2) |
C24 | 0.056 (6) | 0.059 (6) | 0.058 (6) | 0.002 (2) | 0.016 (2) | 0.000 (2) |
C25 | 0.043 (5) | 0.045 (5) | 0.044 (5) | 0.000 (2) | 0.011 (2) | −0.001 (2) |
C26 | 0.027 (5) | 0.028 (5) | 0.029 (5) | 0.000 (2) | 0.007 (2) | −0.001 (2) |
C27 | 0.084 (9) | 0.085 (9) | 0.085 (9) | −0.001 (2) | 0.021 (3) | 0.001 (2) |
C28 | 0.050 (6) | 0.051 (6) | 0.050 (6) | −0.001 (2) | 0.014 (2) | 0.001 (2) |
C29 | 0.047 (18) | 0.047 (18) | 0.046 (18) | 0.000 (2) | 0.013 (5) | −0.001 (2) |
Zn1—O2 | 1.988 (4) | O9—C20 | 1.454 (8) |
Zn1—O6i | 2.034 (4) | O10—C22 | 1.455 (6) |
Zn1—O8 | 2.043 (4) | O10—C29 | 1.456 (6) |
Zn1—O4ii | 2.058 (4) | O10—C26 | 1.457 (6) |
Zn1—O10 | 2.084 (4) | O10—C25 | 1.459 (6) |
Zn2—O5 | 1.998 (4) | C17—C18 | 1.484 (9) |
Zn2—O1 | 2.007 (5) | C17—C21 | 1.485 (9) |
Zn2—O7 | 2.055 (4) | C17—H17A | 0.9900 |
Zn2—O4ii | 2.122 (4) | C17—H17B | 0.9900 |
Zn2—O9 | 2.136 (4) | C17—H17C | 0.9900 |
Zn2—O3ii | 2.319 (4) | C17—H17D | 0.9900 |
F1—C2 | 1.348 (7) | C18—C19 | 1.487 (9) |
F2—C3 | 1.357 (7) | C18—H18A | 0.9900 |
F3—C5 | 1.362 (7) | C18—H18B | 0.9900 |
F4—C6 | 1.338 (7) | C21—C19 | 1.485 (9) |
F5—C11 | 1.344 (7) | C21—H21A | 0.9900 |
F6—C12 | 1.354 (7) | C21—H21B | 0.9900 |
F7—C15 | 1.352 (6) | C19—C20 | 1.511 (10) |
F8—C16 | 1.352 (7) | C19—H19A | 0.9900 |
O1—C7 | 1.262 (7) | C19—H19B | 0.9900 |
O2—C7 | 1.256 (7) | C19—H19C | 0.9900 |
O3—C8 | 1.231 (7) | C19—H19D | 0.9900 |
O4—C8 | 1.280 (7) | C20—H20A | 0.9900 |
O5—C9 | 1.253 (7) | C20—H20B | 0.9900 |
O6—C9 | 1.246 (7) | C22—C23 | 1.498 (8) |
O7—C13 | 1.241 (7) | C22—H22A | 0.9900 |
O8—C13 | 1.243 (7) | C22—H22B | 0.9900 |
C1—C2 | 1.393 (8) | C23—C24 | 1.497 (8) |
C1—C6 | 1.402 (8) | C23—H23A | 0.9900 |
C1—C7 | 1.499 (8) | C23—H23B | 0.9900 |
C2—C3 | 1.372 (8) | C24—C25 | 1.501 (8) |
C3—C4 | 1.382 (8) | C24—H24A | 0.9900 |
C4—C5 | 1.366 (8) | C24—H24B | 0.9900 |
C4—C8 | 1.512 (8) | C25—H25A | 0.9900 |
C5—C6 | 1.365 (8) | C25—H25B | 0.9900 |
C9—C10 | 1.521 (8) | C26—C27 | 1.501 (8) |
C10—C12iii | 1.365 (8) | C26—H26A | 0.9900 |
C10—C11 | 1.387 (8) | C26—H26B | 0.9900 |
C11—C12 | 1.388 (8) | C27—C28 | 1.496 (8) |
C12—C10iii | 1.365 (8) | C27—H27A | 0.9900 |
C13—C14 | 1.522 (8) | C27—H27B | 0.9900 |
C14—C16iv | 1.388 (8) | C28—C29 | 1.498 (8) |
C14—C15 | 1.398 (8) | C28—H28A | 0.9900 |
C15—C16 | 1.358 (8) | C28—H28B | 0.9900 |
C16—C14iv | 1.388 (8) | C29—H29A | 0.9900 |
O9—C17 | 1.420 (9) | C29—H29B | 0.9900 |
O2—Zn1—O6i | 128.65 (18) | C25—O10—Zn1 | 113.8 (6) |
O2—Zn1—O8 | 96.92 (18) | O9—C17—C18 | 107.7 (8) |
O6i—Zn1—O8 | 134.23 (17) | O9—C17—C21 | 106.6 (9) |
O2—Zn1—O4ii | 100.81 (17) | O9—C17—H17A | 110.2 |
O6i—Zn1—O4ii | 87.19 (16) | C18—C17—H17A | 110.2 |
O8—Zn1—O4ii | 88.21 (18) | O9—C17—H17B | 110.2 |
O2—Zn1—O10 | 93.25 (17) | C18—C17—H17B | 110.2 |
O6i—Zn1—O10 | 87.80 (17) | H17A—C17—H17B | 108.5 |
O8—Zn1—O10 | 85.27 (18) | O9—C17—H17C | 110.4 |
O4ii—Zn1—O10 | 165.12 (17) | C21—C17—H17C | 110.4 |
O5—Zn2—O1 | 110.81 (17) | O9—C17—H17D | 110.4 |
O5—Zn2—O7 | 93.75 (18) | C21—C17—H17D | 110.4 |
O1—Zn2—O7 | 90.97 (19) | H17C—C17—H17D | 108.6 |
O5—Zn2—O4ii | 151.45 (16) | C17—C18—C19 | 105.7 (9) |
O1—Zn2—O4ii | 96.62 (18) | C17—C18—H18A | 110.6 |
O7—Zn2—O4ii | 93.52 (16) | C19—C18—H18A | 110.6 |
O5—Zn2—O9 | 88.31 (18) | C17—C18—H18B | 110.6 |
O1—Zn2—O9 | 87.05 (18) | C19—C18—H18B | 110.6 |
O7—Zn2—O9 | 177.55 (19) | H18A—C18—H18B | 108.7 |
O4ii—Zn2—O9 | 85.28 (16) | C17—C21—C19 | 105.8 (9) |
O5—Zn2—O3ii | 92.81 (16) | C17—C21—H21A | 110.6 |
O1—Zn2—O3ii | 155.73 (18) | C19—C21—H21A | 110.6 |
O7—Zn2—O3ii | 93.03 (17) | C17—C21—H21B | 110.6 |
O4ii—Zn2—O3ii | 59.25 (17) | C19—C21—H21B | 110.6 |
O9—Zn2—O3ii | 88.19 (17) | H21A—C21—H21B | 108.7 |
C7—O1—Zn2 | 133.9 (4) | C21—C19—C20 | 104.2 (9) |
C7—O2—Zn1 | 132.9 (4) | C18—C19—C20 | 105.5 (8) |
C8—O3—Zn2v | 85.2 (4) | C18—C19—H19A | 110.6 |
C8—O4—Zn1v | 135.1 (4) | C20—C19—H19A | 110.6 |
C8—O4—Zn2v | 92.9 (4) | C18—C19—H19B | 110.6 |
Zn1v—O4—Zn2v | 112.04 (18) | C20—C19—H19B | 110.6 |
C9—O5—Zn2 | 134.8 (4) | H19A—C19—H19B | 108.8 |
C9—O6—Zn1vi | 113.0 (4) | C21—C19—H19C | 110.9 |
C13—O7—Zn2 | 129.1 (4) | C20—C19—H19C | 110.9 |
C13—O8—Zn1 | 126.5 (4) | C21—C19—H19D | 110.9 |
C2—C1—C6 | 116.3 (5) | C20—C19—H19D | 110.9 |
C2—C1—C7 | 122.6 (5) | H19C—C19—H19D | 108.9 |
C6—C1—C7 | 120.9 (5) | O9—C20—C19 | 106.7 (6) |
F1—C2—C3 | 118.8 (5) | O9—C20—H20A | 110.4 |
F1—C2—C1 | 119.8 (5) | C19—C20—H20A | 110.4 |
C3—C2—C1 | 121.3 (6) | O9—C20—H20B | 110.4 |
F2—C3—C2 | 118.5 (6) | C19—C20—H20B | 110.4 |
F2—C3—C4 | 119.4 (5) | H20A—C20—H20B | 108.6 |
C2—C3—C4 | 122.0 (6) | O10—C22—C23 | 105.5 (10) |
C5—C4—C3 | 116.4 (6) | O10—C22—H22A | 110.6 |
C5—C4—C8 | 119.1 (5) | C23—C22—H22A | 110.6 |
C3—C4—C8 | 124.3 (6) | O10—C22—H22B | 110.6 |
F3—C5—C4 | 119.2 (5) | C23—C22—H22B | 110.6 |
F3—C5—C6 | 117.5 (6) | H22A—C22—H22B | 108.8 |
C4—C5—C6 | 123.1 (6) | C24—C23—C22 | 106.1 (12) |
F4—C6—C5 | 119.4 (5) | C24—C23—H23A | 110.5 |
F4—C6—C1 | 119.9 (5) | C22—C23—H23A | 110.5 |
C5—C6—C1 | 120.6 (6) | C24—C23—H23B | 110.5 |
O2—C7—O1 | 127.7 (6) | C22—C23—H23B | 110.5 |
O2—C7—C1 | 118.4 (6) | H23A—C23—H23B | 108.7 |
O1—C7—C1 | 114.0 (5) | C23—C24—C25 | 107.5 (11) |
O3—C8—O4 | 122.6 (6) | C23—C24—H24A | 110.2 |
O3—C8—C4 | 121.0 (6) | C25—C24—H24A | 110.2 |
O4—C8—C4 | 116.2 (6) | C23—C24—H24B | 110.2 |
O6—C9—O5 | 122.8 (5) | C25—C24—H24B | 110.2 |
O6—C9—C10 | 117.7 (5) | H24A—C24—H24B | 108.5 |
O5—C9—C10 | 119.5 (6) | O10—C25—C24 | 104.7 (9) |
C12iii—C10—C11 | 117.4 (6) | O10—C25—H25A | 110.8 |
C12iii—C10—C9 | 121.7 (6) | C24—C25—H25A | 110.8 |
C11—C10—C9 | 120.8 (6) | O10—C25—H25B | 110.8 |
F5—C11—C12 | 119.5 (5) | C24—C25—H25B | 110.8 |
F5—C11—C10 | 120.2 (5) | H25A—C25—H25B | 108.9 |
C12—C11—C10 | 120.3 (6) | O10—C26—C27 | 98.8 (11) |
F6—C12—C10iii | 119.7 (5) | O10—C26—H26A | 112.0 |
F6—C12—C11 | 118.1 (5) | C27—C26—H26A | 112.0 |
C10iii—C12—C11 | 122.2 (6) | O10—C26—H26B | 112.0 |
O7—C13—O8 | 129.8 (6) | C27—C26—H26B | 112.0 |
O7—C13—C14 | 115.7 (6) | H26A—C26—H26B | 109.7 |
O8—C13—C14 | 114.5 (6) | C28—C27—C26 | 110.3 (14) |
C16iv—C14—C15 | 115.9 (6) | C28—C27—H27A | 109.6 |
C16iv—C14—C13 | 122.1 (6) | C26—C27—H27A | 109.6 |
C15—C14—C13 | 122.0 (6) | C28—C27—H27B | 109.6 |
F7—C15—C16 | 118.8 (6) | C26—C27—H27B | 109.6 |
F7—C15—C14 | 119.0 (6) | H27A—C27—H27B | 108.1 |
C16—C15—C14 | 122.1 (6) | C27—C28—C29 | 101.5 (14) |
F8—C16—C15 | 119.3 (6) | C27—C28—H28A | 111.5 |
F8—C16—C14iv | 118.7 (6) | C29—C28—H28A | 111.5 |
C15—C16—C14iv | 122.0 (6) | C27—C28—H28B | 111.5 |
C17—O9—C20 | 109.7 (5) | C29—C28—H28B | 111.5 |
C17—O9—Zn2 | 125.7 (4) | H28A—C28—H28B | 109.3 |
C20—O9—Zn2 | 124.1 (4) | O10—C29—C28 | 107.4 (11) |
C29—O10—C26 | 107.2 (11) | O10—C29—H29A | 110.2 |
C22—O10—C25 | 108.6 (9) | C28—C29—H29A | 110.2 |
C22—O10—Zn1 | 122.9 (8) | O10—C29—H29B | 110.2 |
C29—O10—Zn1 | 120.9 (12) | C28—C29—H29B | 110.2 |
C26—O10—Zn1 | 126.0 (8) | H29A—C29—H29B | 108.5 |
C6—C1—C2—F1 | −179.6 (6) | F5—C11—C12—C10iii | 178.3 (6) |
C7—C1—C2—F1 | −4.0 (10) | C10—C11—C12—C10iii | −0.6 (11) |
C6—C1—C2—C3 | −2.3 (10) | Zn2—O7—C13—O8 | 23.7 (11) |
C7—C1—C2—C3 | 173.3 (6) | Zn2—O7—C13—C14 | −152.8 (4) |
F1—C2—C3—F2 | 2.6 (10) | Zn1—O8—C13—O7 | −45.1 (11) |
C1—C2—C3—F2 | −174.8 (6) | Zn1—O8—C13—C14 | 131.4 (5) |
F1—C2—C3—C4 | −180.0 (6) | O7—C13—C14—C16iv | 55.4 (9) |
C1—C2—C3—C4 | 2.7 (11) | O8—C13—C14—C16iv | −121.6 (7) |
F2—C3—C4—C5 | 178.0 (6) | O7—C13—C14—C15 | −126.7 (7) |
C2—C3—C4—C5 | 0.6 (10) | O8—C13—C14—C15 | 56.2 (9) |
F2—C3—C4—C8 | 4.0 (10) | C16iv—C14—C15—F7 | −178.0 (6) |
C2—C3—C4—C8 | −173.4 (6) | C13—C14—C15—F7 | 4.0 (10) |
C3—C4—C5—F3 | 179.2 (6) | C16iv—C14—C15—C16 | −1.4 (11) |
C8—C4—C5—F3 | −6.4 (10) | C13—C14—C15—C16 | −179.3 (7) |
C3—C4—C5—C6 | −4.3 (10) | F7—C15—C16—F8 | −0.6 (10) |
C8—C4—C5—C6 | 170.0 (6) | C14—C15—C16—F8 | −177.3 (6) |
F3—C5—C6—F4 | 0.0 (9) | F7—C15—C16—C14iv | 178.1 (6) |
C4—C5—C6—F4 | −176.5 (6) | C14—C15—C16—C14iv | 1.4 (12) |
F3—C5—C6—C1 | −178.7 (6) | C20—O9—C17—C18 | −14.5 (17) |
C4—C5—C6—C1 | 4.8 (11) | Zn2—O9—C17—C18 | 157.5 (15) |
C2—C1—C6—F4 | −180.0 (6) | C20—O9—C17—C21 | 14.8 (14) |
C7—C1—C6—F4 | 4.3 (10) | Zn2—O9—C17—C21 | −173.2 (11) |
C2—C1—C6—C5 | −1.3 (10) | O9—C17—C18—C19 | 22 (3) |
C7—C1—C6—C5 | −177.0 (6) | C21—C17—C18—C19 | −70.7 (8) |
Zn1—O2—C7—O1 | 0.7 (10) | O9—C17—C21—C19 | −26 (2) |
Zn1—O2—C7—C1 | −179.3 (4) | C18—C17—C21—C19 | 70.9 (8) |
Zn2—O1—C7—O2 | −11.3 (11) | C17—C21—C19—C18 | −70.7 (8) |
Zn2—O1—C7—C1 | 168.7 (4) | C17—C21—C19—C20 | 26 (2) |
C2—C1—C7—O2 | 49.9 (9) | C17—C18—C19—C21 | 70.8 (8) |
C6—C1—C7—O2 | −134.7 (7) | C17—C18—C19—C20 | −20 (3) |
C2—C1—C7—O1 | −130.1 (7) | C17—O9—C20—C19 | 1.6 (9) |
C6—C1—C7—O1 | 45.3 (9) | Zn2—O9—C20—C19 | −170.6 (5) |
Zn2v—O3—C8—O4 | 0.1 (6) | C21—C19—C20—O9 | −17.1 (14) |
Zn2v—O3—C8—C4 | −175.0 (6) | C18—C19—C20—O9 | 11.8 (17) |
Zn1v—O4—C8—O3 | 125.7 (6) | C29—O10—C22—C23 | −94 (13) |
Zn2v—O4—C8—O3 | −0.1 (7) | C26—O10—C22—C23 | −5 (2) |
Zn1v—O4—C8—C4 | −59.0 (8) | C25—O10—C22—C23 | −28 (3) |
Zn2v—O4—C8—C4 | 175.3 (5) | Zn1—O10—C22—C23 | −164.3 (13) |
Zn1v—O4—C8—Zn2v | 125.8 (5) | O10—C22—C23—C24 | 18 (3) |
C5—C4—C8—O3 | 73.2 (9) | C22—C23—C24—C25 | −2 (2) |
C3—C4—C8—O3 | −113.0 (8) | C22—O10—C25—C24 | 27 (2) |
C5—C4—C8—O4 | −102.3 (7) | C29—O10—C25—C24 | 32 (2) |
C3—C4—C8—O4 | 71.6 (9) | C26—O10—C25—C24 | −64 (2) |
Zn1vi—O6—C9—O5 | −11.4 (8) | Zn1—O10—C25—C24 | 167.3 (13) |
Zn1vi—O6—C9—C10 | 167.6 (4) | C23—C24—C25—O10 | −15 (2) |
Zn2—O5—C9—O6 | −149.5 (5) | C22—O10—C26—C27 | −44 (2) |
Zn2—O5—C9—C10 | 31.5 (9) | C29—O10—C26—C27 | −38 (2) |
O6—C9—C10—C12iii | −106.3 (7) | C25—O10—C26—C27 | 53 (2) |
O5—C9—C10—C12iii | 72.7 (8) | Zn1—O10—C26—C27 | 114.9 (15) |
O6—C9—C10—C11 | 73.4 (8) | O10—C26—C27—C28 | 32 (3) |
O5—C9—C10—C11 | −107.6 (7) | C26—C27—C28—C29 | −14 (3) |
C12iii—C10—C11—F5 | −178.4 (6) | C22—O10—C29—C28 | 124 (15) |
C9—C10—C11—F5 | 2.0 (9) | C26—O10—C29—C28 | 32 (3) |
C12iii—C10—C11—C12 | 0.6 (10) | C25—O10—C29—C28 | 9 (3) |
C9—C10—C11—C12 | −179.1 (6) | Zn1—O10—C29—C28 | −122.8 (17) |
F5—C11—C12—F6 | −0.7 (9) | C27—C28—C29—O10 | −10 (3) |
C10—C11—C12—F6 | −179.7 (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) x−1/2, −y+1/2, z−1/2; (vi) −x+3/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn2(C8F4O4)2(C4H8O)2] |
Mr | 747.11 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 11.9339 (8), 12.4369 (9), 17.9627 (12) |
β (°) | 104.051 (1) |
V (Å3) | 2586.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.97 |
Crystal size (mm) | 0.10 × 0.05 × 0.05 |
Data collection | |
Diffractometer | SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.827, 0.908 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16096, 5980, 2859 |
Rint | 0.111 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.139, 0.94 |
No. of reflections | 5980 |
No. of parameters | 444 |
No. of restraints | 81 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.66, −0.78 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).
Acknowledgements
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
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).