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Acta Cryst. (2007). E63, m1889-m1890    [ doi:10.1107/S1600536807028437 ]

Poly[tetraaquabis([mu]4-cyclohexane-1,4-dicarboxylato-[kappa]6O:O,O':O'':O'',O''')hemi([mu]2-cyclohexane-1,4-dicarboxylato-[kappa]2O:O')hemi([mu]2-cyclohexane-1,4-dicarboxylato-[kappa]4O,O':O'',O''')dipraseodymium(III)]

M. Yu, S.-X. Liu, L.-H. Xie, R.-G. Cao and Y.-H. Ren

Abstract top

The title compound, [Pr2(C8H10O4)3(H2O)4]n is a three-dimensional metal-organic framework built of chains of edge-sharing PrIII polyhedra by the e,e-trans-cyclohexane-1,4-dicarboxylate (chdc) dianions. There are two types of Pr atoms (one in a ten-coordinate and the other in a nine-coordinate geometry) and four types of chdc ligands. One Pr atom is coordinated by eight carboxylate O atoms from five chdc and two water molecules, whereas the other is coordinated by seven carboxylate O atoms from five chdc and two water molecules. Two of the four chdc ligands are located on inversion centers. The ligation of alternate Pr atoms by the carboxylate groups of chdc ligands leads to an infinite chain; the chains are further connected with six neighboring chains through the chdc ligands, resulting in a three-dimensional network.

Comment top

Cyclohexane-1,4-dicarboxylic acid (chdcH2) is a flexible ligand for constructing functional metal-organic frameworks (Kurmoo et al., 2003, Kurmoo et al., 2006, Qi et al., 2003, Rao et al., 2007). In our previous work, we have also isolated a photoluminescent zinc cyclohexane-1,4-dicarboxylate (Yu et al., 2007). When investigating the reaction of chdcH2 and Pr3+ ions, a compound formulated as [Pr2(C8H10O4)3(H2O)4]n (I) was obtained.

The compound is a three-dimensional framework built from infinite chains of edge-sharing Pr polyhedra that are interconnected by the –C6H12– cyclohexane rings of chdc ligands. There are two Pr atoms, three chdc and four coordinated water molecules in the asymmetric unit (Figure 1). There are four types of chdc ligands and two types of Pr atoms. The four chdc dianions are in an e,e-trans conformation. Their coordination modes, shown in Figure 2, are denoted as α, β, γ and δ. The Pr1 is coordinated by eight carboxyl O atoms from five chdc (two α, two β, one γ) and two water molecules in a distorted dicapped square-antiprismatic enviroment whereas the Pr2 is coordinated by seven carboxyl O atoms from five chdc (two α, two β, one δ) and two water molecules in a distorted tricapped trigonal-prismatic enviroment. The Pr—O bond lengths range from 2.451 (3) to 2.828 (3) Å. There are hydrogen bonding interactions involving the water molecules and some carboxyl O atoms. The ligation of alternating Pr1 and Pr2 atoms by the carboxyl groups of chdc ligands leads to an infinite chain (Figure 3). Each chain connects with six neighboring chains through chdc ligands to result in a three-dimensional framework (Figure 4).

Related literature top

For related literature on metal complexes of transcyclohexane-1,4-dicarboxylic acid, see: Kurmoo et al. (2003, 2006); Qi et al. (2003); Rao et al. (2007); Yu et al. (2007); Rao et al. (2007).

Experimental top

A mixture of PrCl3.6H2O (0.5 mmol, 0.178 g), chdcH2 (0.8 mmol, 0.137 g), and water (10 ml) adjusted by dilute NaOH solution to around pH 4 was sealed in Teflon-lined autoclave and heated at 180 °C for 4 days, followed by slow cooling to room temperature. Compound (I) was collected as green block crystals with yield about 75% based on Pr.

Refinement top

H atoms on water molecules were located in a difference Fourier map, and fixed with O—H = 0.85 Å and Uiso(H) = 1.2 Ueq(O). The others on C atoms are placed in calculated positions and refined in the riding model approximation with C—H = 0.97 or 0.98 Å and Uiso(H) = 1.2 Ueq(C). The highest peak and deepest hole in the final electron-density difference map were 0.506 Å and -0.897 Å, respectively.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. ORTEP view of the asymmetric unit of (I) with displacement ellipsoids drawn at 50% probability level.
[Figure 2] Fig. 2. The coordination fashions of the four types of chdc dianions).
[Figure 3] Fig. 3. Perspective view of the infinite chain with Pr atoms represented as polyhedra.
[Figure 4] Fig. 4. Perspective view of the three-dimensional metal-organic framework along the direction of the infinite chains.
Poly[tetraaquabis(µ4-cyclohexane-1,4-dicarboxylato- κ6O:O,O':O'':O'',O''')hemi(µ2-cyclohexane- 1,4-dicarboxylato-κ2O:O')hemi(µ2-cyclohexane-1,4-dicarboxylato- κ4O,O':O'',O''')dipraseodymium(III)] top
Crystal data top
[Pr2(C8H10O4)3(H2O)4]Z = 2
Mr = 864.36F(000) = 856
Triclinic, P1Dx = 1.960 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.439 (2) ÅCell parameters from 776 reflections
b = 11.964 (2) Åθ = 3.0–25.0°
c = 12.343 (3) ŵ = 3.36 mm−1
α = 94.794 (18)°T = 298 K
β = 115.82 (3)°Block, white
γ = 101.128 (12)°0.27 × 0.26 × 0.24 mm
V = 1464.9 (7) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		5116 independent reflections
Radiation source: fine-focus sealed tube4548 reflections with I > 2σ(I)
graphiteRint = 0.029
Detector resolution: 0 pixels mm-1θmax = 25.0°, θmin = 3.0°
ω scansh = −13→12
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −14→14
Tmin = 0.419, Tmax = 0.443l = −14→14
11551 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0084P)2 + 2.1565P]
where P = (Fo2 + 2Fc2)/3
5116 reflections(Δ/σ)max = 0.001
379 parametersΔρmax = 0.51 e Å−3
0 restraintsΔρmin = −0.90 e Å−3
Crystal data top
[Pr2(C8H10O4)3(H2O)4]γ = 101.128 (12)°
Mr = 864.36V = 1464.9 (7) Å3
Triclinic, P1Z = 2
a = 11.439 (2) ÅMo Kα radiation
b = 11.964 (2) ŵ = 3.36 mm−1
c = 12.343 (3) ÅT = 298 K
α = 94.794 (18)°0.27 × 0.26 × 0.24 mm
β = 115.82 (3)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		5116 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4548 reflections with I > 2σ(I)
Tmin = 0.419, Tmax = 0.443Rint = 0.029
11551 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.051Δρmax = 0.51 e Å−3
S = 1.08Δρmin = −0.90 e Å−3
5116 reflectionsAbsolute structure: ?
379 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Pr10.488253 (18)0.430131 (16)0.319055 (17)0.01375 (6)
Pr20.462496 (17)0.167914 (16)0.025852 (16)0.01346 (6)
C10.7123 (3)0.4174 (3)0.2526 (3)0.0201 (8)
C20.8420 (3)0.4200 (3)0.2469 (3)0.0226 (8)
H20.82210.36920.17120.027*
C30.9097 (4)0.5418 (4)0.2471 (4)0.0360 (11)
H3A0.92430.59360.31900.043*
H3B0.85150.56790.17520.043*
C40.9352 (4)0.3750 (3)0.3572 (4)0.0244 (8)
H4A0.94350.41760.43170.029*
H4B0.89450.29390.35020.029*
C51.0442 (4)0.5469 (4)0.2471 (4)0.0404 (12)
H5A1.02920.49750.17330.048*
H5B1.08470.62570.24640.048*
C61.0758 (4)0.3865 (3)0.3678 (4)0.0226 (8)
H6A1.13350.36880.44580.027*
H6B1.07000.33010.30330.027*
C71.1394 (3)0.5078 (3)0.3584 (3)0.0191 (8)
H71.16090.56250.43210.023*
C81.2686 (3)0.5033 (3)0.3541 (3)0.0169 (7)
C90.2286 (4)0.2082 (3)0.0562 (3)0.0201 (8)
C100.0992 (3)0.2270 (3)0.0508 (4)0.0222 (8)
H100.11720.30630.09290.027*
C110.0512 (3)0.1417 (3)0.1181 (3)0.0206 (8)
H11A0.04980.06400.08730.025*
H11B0.11450.16140.20480.025*
C12−0.0075 (4)0.2124 (4)−0.0817 (4)0.0287 (9)
H12A−0.02060.1365−0.12620.034*
H12B0.02330.2705−0.12030.034*
C13−0.0887 (3)0.1431 (3)0.1022 (3)0.0226 (8)
H13A−0.08290.21520.14890.027*
H13B−0.11960.07980.13540.027*
C14−0.1411 (4)0.2248 (4)−0.0888 (4)0.0282 (9)
H14A−0.12910.3010−0.04550.034*
H14B−0.20660.2169−0.17380.034*
C15−0.1914 (3)0.1317 (3)−0.0317 (3)0.0170 (7)
H15−0.20290.0556−0.07670.020*
C16−0.3234 (3)0.1365 (3)−0.0334 (3)0.0175 (8)
C170.4813 (4)0.2186 (3)0.4184 (3)0.0242 (9)
C180.4814 (5)0.1149 (3)0.4800 (4)0.0323 (10)
H180.44690.12890.53870.039*
C190.6205 (5)0.0967 (4)0.5510 (4)0.0467 (12)
H19A0.67860.16560.61250.056*
H19B0.65820.08410.49570.056*
C200.3862 (5)0.0083 (4)0.3863 (4)0.0440 (12)
H20A0.4165−0.00710.32570.053*
H20B0.29730.02130.34450.053*
C210.2456 (4)0.1272 (3)−0.2847 (3)0.0220 (8)
C220.1333 (4)0.0380 (3)−0.3917 (3)0.0273 (9)
H220.1574−0.0363−0.38800.033*
C230.0041 (5)0.0232 (5)−0.3810 (4)0.0489 (13)
H23A−0.02000.0966−0.38190.059*
H23B0.01810.0004−0.30350.059*
C240.1101 (5)0.0684 (5)−0.5141 (4)0.0491 (13)
H24A0.19170.0748−0.52220.059*
H24B0.08870.1430−0.51870.059*
O10.6014 (2)0.3505 (2)0.1740 (2)0.0260 (6)
O20.7147 (3)0.4855 (2)0.3370 (3)0.0353 (7)
O30.2670 (2)0.4772 (2)0.2521 (2)0.0271 (6)
O40.6233 (2)0.4813 (2)0.5478 (2)0.0222 (6)
O50.3421 (2)0.2627 (2)0.1422 (2)0.0251 (6)
O60.2228 (3)0.1361 (2)−0.0272 (3)0.0350 (7)
O70.3943 (2)−0.0465 (2)0.0225 (2)0.0223 (6)
O80.6411 (3)0.2292 (2)−0.0383 (2)0.0250 (6)
O90.5688 (3)0.2502 (2)0.3825 (3)0.0291 (6)
O100.3942 (3)0.2739 (2)0.4051 (2)0.0242 (6)
O110.3319 (3)0.0925 (2)−0.1981 (2)0.0242 (6)
O120.2456 (3)0.2317 (2)−0.2863 (2)0.0333 (7)
O1W0.5733 (3)0.6472 (2)0.3677 (2)0.0289 (6)
H1W0.59980.67780.44180.035*
H2W0.63160.67580.34560.035*
O2W0.4036 (3)0.5128 (2)0.1098 (2)0.0301 (6)
H3W0.45830.56310.09800.036*
H4W0.34280.54570.10620.036*
O3W0.6203 (3)0.1250 (2)0.2213 (2)0.0406 (8)
H5W0.63400.15820.29090.049*
H6W0.63680.05890.22690.049*
O4W0.4041 (3)0.3423 (2)−0.0683 (2)0.0238 (6)
H7W0.34850.3204−0.14400.029*
H8W0.38950.3857−0.02000.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pr10.01010 (10)0.01528 (10)0.01643 (11)0.00264 (8)0.00685 (8)0.00308 (8)
Pr20.00806 (10)0.01611 (11)0.01489 (11)0.00227 (8)0.00499 (8)−0.00001 (8)
C10.0129 (18)0.0218 (19)0.021 (2)0.0011 (16)0.0051 (16)0.0039 (16)
C20.0127 (18)0.033 (2)0.021 (2)0.0034 (17)0.0091 (16)−0.0012 (16)
C30.018 (2)0.045 (3)0.058 (3)0.018 (2)0.022 (2)0.032 (2)
C40.0162 (19)0.023 (2)0.033 (2)0.0020 (17)0.0118 (18)0.0056 (17)
C50.022 (2)0.063 (3)0.055 (3)0.023 (2)0.024 (2)0.043 (3)
C60.0137 (18)0.025 (2)0.029 (2)0.0056 (16)0.0093 (17)0.0049 (17)
C70.0117 (18)0.0210 (19)0.027 (2)0.0048 (15)0.0107 (16)0.0029 (15)
C80.0105 (18)0.0137 (17)0.026 (2)0.0021 (15)0.0082 (17)0.0032 (15)
C90.0144 (19)0.0145 (18)0.031 (2)0.0001 (16)0.0117 (18)0.0055 (16)
C100.0111 (18)0.0197 (19)0.035 (2)0.0019 (16)0.0123 (17)−0.0006 (16)
C110.0141 (18)0.028 (2)0.0193 (19)0.0080 (16)0.0070 (16)0.0009 (16)
C120.019 (2)0.041 (2)0.038 (2)0.0105 (19)0.0202 (19)0.022 (2)
C130.0158 (19)0.031 (2)0.022 (2)0.0060 (17)0.0100 (17)0.0039 (16)
C140.0145 (19)0.038 (2)0.038 (2)0.0088 (18)0.0143 (19)0.0211 (19)
C150.0125 (17)0.0184 (18)0.022 (2)0.0033 (15)0.0102 (16)0.0030 (15)
C160.0129 (18)0.023 (2)0.0152 (18)0.0029 (16)0.0069 (15)0.0004 (15)
C170.035 (2)0.0175 (19)0.019 (2)0.0034 (18)0.0133 (18)0.0015 (15)
C180.048 (3)0.022 (2)0.037 (3)0.015 (2)0.025 (2)0.0127 (18)
C190.048 (3)0.026 (2)0.041 (3)−0.007 (2)0.004 (2)0.013 (2)
C200.043 (3)0.032 (2)0.040 (3)0.001 (2)0.005 (2)0.019 (2)
C210.019 (2)0.024 (2)0.019 (2)0.0024 (17)0.0078 (17)0.0016 (16)
C220.023 (2)0.022 (2)0.023 (2)0.0067 (18)−0.0003 (17)−0.0024 (16)
C230.035 (3)0.072 (4)0.018 (2)−0.015 (3)0.008 (2)−0.005 (2)
C240.032 (3)0.071 (4)0.025 (2)−0.019 (2)0.012 (2)−0.007 (2)
O10.0141 (13)0.0260 (14)0.0273 (15)−0.0042 (12)0.0051 (12)−0.0017 (12)
O20.0206 (15)0.0397 (17)0.0434 (18)0.0003 (13)0.0197 (14)−0.0140 (14)
O30.0164 (13)0.0446 (17)0.0224 (15)0.0104 (13)0.0106 (12)0.0020 (12)
O40.0118 (13)0.0282 (14)0.0225 (14)0.0060 (11)0.0043 (12)0.0032 (11)
O50.0131 (13)0.0353 (16)0.0244 (15)0.0034 (12)0.0084 (12)0.0017 (12)
O60.0128 (14)0.0319 (16)0.0513 (19)−0.0004 (12)0.0134 (14)−0.0151 (14)
O70.0172 (13)0.0217 (14)0.0327 (16)0.0043 (12)0.0158 (12)0.0064 (11)
O80.0199 (14)0.0232 (14)0.0402 (17)0.0076 (12)0.0201 (13)0.0068 (12)
O90.0427 (17)0.0249 (14)0.0368 (17)0.0188 (14)0.0280 (15)0.0143 (12)
O100.0315 (15)0.0195 (13)0.0281 (15)0.0088 (13)0.0181 (13)0.0066 (11)
O110.0216 (14)0.0284 (14)0.0173 (14)0.0105 (12)0.0030 (12)0.0017 (11)
O120.0361 (17)0.0226 (15)0.0232 (15)0.0028 (13)−0.0003 (13)0.0040 (12)
O1W0.0431 (17)0.0210 (14)0.0289 (16)0.0029 (13)0.0248 (14)0.0016 (12)
O2W0.0356 (16)0.0315 (15)0.0332 (16)0.0112 (14)0.0223 (14)0.0142 (13)
O3W0.061 (2)0.0359 (17)0.0158 (15)0.0285 (16)0.0040 (15)0.0004 (12)
O4W0.0281 (15)0.0207 (13)0.0180 (14)0.0050 (12)0.0079 (12)−0.0009 (11)
Geometric parameters (Å, °) top
Pr1—O22.451 (3)C11—H11A0.9700
Pr1—O32.493 (2)C11—H11B0.9700
Pr1—O42.506 (3)C12—C141.529 (5)
Pr1—O1W2.511 (3)C12—H12A0.9700
Pr1—O102.516 (3)C12—H12B0.9700
Pr1—O52.524 (3)C13—C151.530 (5)
Pr1—O92.552 (3)C13—H13A0.9700
Pr1—O2W2.684 (3)C13—H13B0.9700
Pr1—O4i2.740 (2)C14—C151.519 (5)
Pr1—O12.828 (3)C14—H14A0.9700
Pr2—O62.466 (3)C14—H14B0.9700
Pr2—O12.471 (3)C15—C161.513 (4)
Pr2—O3W2.472 (3)C15—H150.9800
Pr2—O112.481 (3)C16—O8v1.250 (4)
Pr2—O82.503 (2)C16—O7vi1.271 (4)
Pr2—O72.525 (3)C17—O101.261 (4)
Pr2—O4W2.533 (2)C17—O91.269 (5)
Pr2—O7ii2.602 (2)C17—C181.507 (5)
Pr2—O52.702 (2)C18—C201.507 (6)
C1—O21.255 (4)C18—C191.516 (6)
C1—O11.263 (4)C18—H180.9800
C1—C21.510 (5)C19—C20vii1.535 (6)
C2—C31.511 (6)C19—H19A0.9700
C2—C41.537 (5)C19—H19B0.9700
C2—H20.9800C20—C19vii1.535 (6)
C3—C51.527 (5)C20—H20A0.9700
C3—H3A0.9700C20—H20B0.9700
C3—H3B0.9700C21—O121.252 (4)
C4—C61.534 (5)C21—O111.266 (4)
C4—H4A0.9700C21—C221.513 (5)
C4—H4B0.9700C22—C241.505 (6)
C5—C71.514 (5)C22—C231.519 (6)
C5—H5A0.9700C22—H220.9800
C5—H5B0.9700C23—C24viii1.523 (6)
C6—C71.530 (5)C23—H23A0.9700
C6—H6A0.9700C23—H23B0.9700
C6—H6B0.9700C24—C23viii1.523 (6)
C7—C81.513 (4)C24—H24A0.9700
C7—H70.9800C24—H24B0.9700
C8—O3iii1.262 (4)O1W—H1W0.8500
C8—O4iv1.264 (4)O1W—H2W0.8500
C9—O61.257 (4)O2W—H3W0.8499
C9—O51.263 (4)O2W—H4W0.8501
C9—C101.513 (5)O3W—H5W0.8499
C10—C121.525 (5)O3W—H6W0.8500
C10—C111.535 (5)O4W—H7W0.8500
C10—H100.9800O4W—H8W0.8500
C11—C131.528 (5)
O2—Pr1—O3146.79 (10)C6—C7—H7108.8
O2—Pr1—O480.40 (9)O3iii—C8—O4iv119.7 (3)
O3—Pr1—O4110.50 (8)O3iii—C8—C7119.7 (3)
O2—Pr1—O1W70.10 (9)O4iv—C8—C7120.5 (3)
O3—Pr1—O1W82.36 (9)O6—C9—O5119.1 (3)
O4—Pr1—O1W74.75 (9)O6—C9—C10119.0 (3)
O2—Pr1—O10128.45 (10)O5—C9—C10121.9 (3)
O3—Pr1—O1084.50 (9)C9—C10—C12110.8 (3)
O4—Pr1—O1072.71 (9)C9—C10—C11109.0 (3)
O1W—Pr1—O10137.74 (8)C12—C10—C11111.2 (3)
O2—Pr1—O5110.28 (8)C9—C10—H10108.6
O3—Pr1—O580.23 (9)C12—C10—H10108.6
O4—Pr1—O5143.25 (8)C11—C10—H10108.6
O1W—Pr1—O5141.92 (9)C13—C11—C10112.6 (3)
O10—Pr1—O573.60 (8)C13—C11—H11A109.1
O2—Pr1—O979.70 (10)C10—C11—H11A109.1
O3—Pr1—O9132.96 (9)C13—C11—H11B109.1
O4—Pr1—O974.98 (9)C10—C11—H11B109.1
O1W—Pr1—O9140.08 (10)H11A—C11—H11B107.8
O10—Pr1—O951.45 (8)C10—C12—C14111.4 (3)
O5—Pr1—O972.78 (9)C10—C12—H12A109.3
O2—Pr1—O2W87.07 (10)C14—C12—H12A109.3
O3—Pr1—O2W65.97 (9)C10—C12—H12B109.3
O4—Pr1—O2W145.39 (8)C14—C12—H12B109.3
O1W—Pr1—O2W70.65 (9)H12A—C12—H12B108.0
O10—Pr1—O2W137.12 (9)C11—C13—C15112.9 (3)
O5—Pr1—O2W71.35 (9)C11—C13—H13A109.0
O9—Pr1—O2W134.29 (8)C15—C13—H13A109.0
O2—Pr1—O4i131.45 (8)C11—C13—H13B109.0
O3—Pr1—O4i49.08 (8)C15—C13—H13B109.0
O4—Pr1—O4i61.45 (9)H13A—C13—H13B107.8
O1W—Pr1—O4i71.63 (8)C15—C14—C12109.3 (3)
O10—Pr1—O4i69.45 (8)C15—C14—H14A109.8
O5—Pr1—O4i118.26 (8)C12—C14—H14A109.8
O9—Pr1—O4i114.39 (8)C15—C14—H14B109.8
O2W—Pr1—O4i107.14 (8)C12—C14—H14B109.8
O2—Pr1—O147.90 (8)H14A—C14—H14B108.3
O3—Pr1—O1128.93 (8)C16—C15—C14113.7 (3)
O4—Pr1—O1120.33 (8)C16—C15—C13107.2 (3)
O1W—Pr1—O1105.56 (8)C14—C15—C13110.2 (3)
O10—Pr1—O1113.86 (8)C16—C15—H15108.5
O5—Pr1—O162.49 (8)C14—C15—H15108.5
O9—Pr1—O169.17 (8)C13—C15—H15108.5
O2W—Pr1—O169.60 (8)O8v—C16—O7vi120.1 (3)
O4i—Pr1—O1176.43 (7)O8v—C16—C15120.7 (3)
O6—Pr2—O1112.17 (9)O7vi—C16—C15119.1 (3)
O6—Pr2—O3W119.77 (11)O10—C17—O9120.9 (3)
O1—Pr2—O3W70.03 (10)O10—C17—C18118.7 (3)
O6—Pr2—O1172.91 (9)O9—C17—C18120.4 (4)
O1—Pr2—O11140.80 (9)C20—C18—C17109.7 (3)
O3W—Pr2—O11143.49 (8)C20—C18—C19111.4 (4)
O6—Pr2—O8146.90 (10)C17—C18—C19113.1 (4)
O1—Pr2—O878.18 (9)C20—C18—H18107.5
O3W—Pr2—O893.32 (10)C17—C18—H18107.5
O11—Pr2—O879.83 (9)C19—C18—H18107.5
O6—Pr2—O777.83 (9)C18—C19—C20vii110.5 (4)
O1—Pr2—O7139.66 (9)C18—C19—H19A109.6
O3W—Pr2—O771.37 (9)C20vii—C19—H19A109.6
O11—Pr2—O779.35 (9)C18—C19—H19B109.6
O8—Pr2—O7115.48 (8)C20vii—C19—H19B109.6
O6—Pr2—O4W77.50 (9)H19A—C19—H19B108.1
O1—Pr2—O4W69.00 (9)C18—C20—C19vii110.2 (4)
O3W—Pr2—O4W139.02 (9)C18—C20—H20A109.6
O11—Pr2—O4W74.81 (8)C19vii—C20—H20A109.6
O8—Pr2—O4W77.52 (8)C18—C20—H20B109.6
O7—Pr2—O4W148.44 (8)C19vii—C20—H20B109.6
O6—Pr2—O7ii135.00 (8)H20A—C20—H20B108.1
O1—Pr2—O7ii112.57 (8)O12—C21—O11123.8 (3)
O3W—Pr2—O7ii72.41 (9)O12—C21—C22117.4 (3)
O11—Pr2—O7ii75.79 (8)O11—C21—C22118.7 (3)
O8—Pr2—O7ii50.64 (8)C24—C22—C21113.1 (4)
O7—Pr2—O7ii65.17 (9)C24—C22—C23109.5 (3)
O4W—Pr2—O7ii123.70 (8)C21—C22—C23109.8 (3)
O6—Pr2—O549.44 (8)C24—C22—H22108.1
O1—Pr2—O565.04 (8)C21—C22—H22108.1
O3W—Pr2—O589.86 (9)C23—C22—H22108.1
O11—Pr2—O5118.55 (8)C22—C23—C24viii111.1 (4)
O8—Pr2—O5139.43 (8)C22—C23—H23A109.4
O7—Pr2—O5103.84 (8)C24viii—C23—H23A109.4
O4W—Pr2—O573.90 (8)C22—C23—H23B109.4
O7ii—Pr2—O5161.22 (8)C24viii—C23—H23B109.4
O2—C1—O1119.1 (3)H23A—C23—H23B108.0
O2—C1—C2118.7 (3)C22—C24—C23viii111.3 (4)
O1—C1—C2122.2 (3)C22—C24—H24A109.4
C1—C2—C3110.6 (3)C23viii—C24—H24A109.4
C1—C2—C4109.2 (3)C22—C24—H24B109.4
C3—C2—C4110.2 (3)C23viii—C24—H24B109.4
C1—C2—H2108.9H24A—C24—H24B108.0
C3—C2—H2108.9C1—O1—Pr2152.8 (2)
C4—C2—H2108.9C1—O1—Pr187.1 (2)
C2—C3—C5111.3 (3)Pr2—O1—Pr1114.27 (9)
C2—C3—H3A109.4C1—O2—Pr1105.5 (2)
C5—C3—H3A109.4C8v—O3—Pr1100.9 (2)
C2—C3—H3B109.4C8iv—O4—Pr1152.0 (2)
C5—C3—H3B109.4C8iv—O4—Pr1i89.1 (2)
H3A—C3—H3B108.0Pr1—O4—Pr1i118.55 (9)
C6—C4—C2113.3 (3)C9—O5—Pr1150.7 (2)
C6—C4—H4A108.9C9—O5—Pr289.8 (2)
C2—C4—H4A108.9Pr1—O5—Pr2116.90 (9)
C6—C4—H4B108.9C9—O6—Pr2101.3 (2)
C2—C4—H4B108.9C16vi—O7—Pr2153.8 (2)
H4A—C4—H4B107.7C16vi—O7—Pr2ii91.35 (19)
C7—C5—C3111.4 (3)Pr2—O7—Pr2ii114.83 (9)
C7—C5—H5A109.3C16iii—O8—Pr296.6 (2)
C3—C5—H5A109.3C17—O9—Pr192.8 (2)
C7—C5—H5B109.3C17—O10—Pr194.7 (2)
C3—C5—H5B109.3C21—O11—Pr2132.8 (2)
H5A—C5—H5B108.0Pr1—O1W—H1W114.7
C7—C6—C4112.8 (3)Pr1—O1W—H2W116.7
C7—C6—H6A109.0H1W—O1W—H2W109.1
C4—C6—H6A109.0Pr1—O2W—H3W120.1
C7—C6—H6B109.0Pr1—O2W—H4W107.1
C4—C6—H6B109.0H3W—O2W—H4W104.8
H6A—C6—H6B107.8Pr2—O3W—H5W123.1
C8—C7—C5111.8 (3)Pr2—O3W—H6W122.1
C8—C7—C6107.4 (3)H5W—O3W—H6W109.1
C5—C7—C6111.2 (3)Pr2—O4W—H7W109.8
C8—C7—H7108.8Pr2—O4W—H8W108.2
C5—C7—H7108.8H7W—O4W—H8W121.8
O2—C1—C2—C3−53.6 (5)O1—Pr1—O4—C8iv5.7 (5)
O1—C1—C2—C3125.1 (4)O2—Pr1—O4—Pr1i148.93 (12)
O2—C1—C2—C467.8 (4)O3—Pr1—O4—Pr1i1.51 (13)
O1—C1—C2—C4−113.5 (4)O1W—Pr1—O4—Pr1i77.09 (11)
C1—C2—C3—C5177.5 (3)O10—Pr1—O4—Pr1i−75.57 (11)
C4—C2—C3—C556.6 (5)O5—Pr1—O4—Pr1i−99.92 (14)
C1—C2—C4—C6−173.7 (3)O9—Pr1—O4—Pr1i−129.26 (12)
C3—C2—C4—C6−52.0 (4)O2W—Pr1—O4—Pr1i78.59 (16)
C2—C3—C5—C7−59.6 (5)O4i—Pr1—O4—Pr1i0.0
C2—C4—C6—C749.4 (4)O1—Pr1—O4—Pr1i176.45 (8)
C3—C5—C7—C8175.4 (4)O6—C9—O5—Pr1162.5 (3)
C3—C5—C7—C655.4 (5)C10—C9—O5—Pr1−17.6 (7)
C4—C6—C7—C8−173.0 (3)O6—C9—O5—Pr25.9 (3)
C4—C6—C7—C5−50.4 (4)C10—C9—O5—Pr2−174.2 (3)
C5—C7—C8—O3iii−32.6 (5)O2—Pr1—O5—C9−148.2 (5)
C6—C7—C8—O3iii89.6 (4)O3—Pr1—O5—C9−0.9 (5)
C5—C7—C8—O4iv151.6 (4)O4—Pr1—O5—C9110.4 (5)
C6—C7—C8—O4iv−86.2 (4)O1W—Pr1—O5—C9−64.9 (5)
O6—C9—C10—C12−33.1 (5)O10—Pr1—O5—C986.2 (5)
O5—C9—C10—C12147.0 (4)O9—Pr1—O5—C9140.1 (5)
O6—C9—C10—C1189.6 (4)O2W—Pr1—O5—C9−68.7 (5)
O5—C9—C10—C11−90.3 (4)O4i—Pr1—O5—C931.2 (5)
C9—C10—C11—C13−172.1 (3)O1—Pr1—O5—C9−144.8 (5)
C12—C10—C11—C13−49.7 (4)O2—Pr1—O5—Pr25.38 (14)
C9—C10—C12—C14177.0 (3)O3—Pr1—O5—Pr2152.67 (12)
C11—C10—C12—C1455.5 (4)O4—Pr1—O5—Pr2−96.01 (14)
C10—C11—C13—C1549.9 (4)O1W—Pr1—O5—Pr288.67 (15)
C10—C12—C14—C15−60.7 (4)O10—Pr1—O5—Pr2−120.24 (12)
C12—C14—C15—C16179.7 (3)O9—Pr1—O5—Pr2−66.31 (11)
C12—C14—C15—C1359.3 (4)O2W—Pr1—O5—Pr284.88 (11)
C11—C13—C15—C16−179.0 (3)O4i—Pr1—O5—Pr2−175.23 (8)
C11—C13—C15—C14−54.8 (4)O1—Pr1—O5—Pr28.71 (9)
C14—C15—C16—O8v−24.5 (5)O6—Pr2—O5—C9−3.5 (2)
C13—C15—C16—O8v97.6 (4)O1—Pr2—O5—C9157.6 (2)
C14—C15—C16—O7vi159.5 (3)O3W—Pr2—O5—C9−134.4 (2)
C13—C15—C16—O7vi−78.4 (4)O11—Pr2—O5—C921.6 (2)
O10—C17—C18—C2086.4 (5)O8—Pr2—O5—C9130.6 (2)
O9—C17—C18—C20−94.6 (5)O7—Pr2—O5—C9−63.7 (2)
O10—C17—C18—C19−148.6 (4)O4W—Pr2—O5—C983.7 (2)
O9—C17—C18—C1930.3 (5)O7ii—Pr2—O5—C9−115.4 (3)
C20—C18—C19—C20vii−57.2 (6)O6—Pr2—O5—Pr1−170.85 (18)
C17—C18—C19—C20vii178.8 (4)O1—Pr2—O5—Pr1−9.76 (10)
C17—C18—C20—C19vii−177.0 (4)O3W—Pr2—O5—Pr158.18 (12)
C19—C18—C20—C19vii57.1 (6)O11—Pr2—O5—Pr1−145.81 (10)
O12—C21—C22—C2447.3 (5)O8—Pr2—O5—Pr1−36.76 (18)
O11—C21—C22—C24−134.1 (4)O7—Pr2—O5—Pr1128.93 (11)
O12—C21—C22—C23−75.4 (5)O4W—Pr2—O5—Pr1−83.68 (12)
O11—C21—C22—C23103.3 (4)O7ii—Pr2—O5—Pr177.2 (3)
C24—C22—C23—C24viii56.7 (6)O5—C9—O6—Pr2−6.6 (4)
C21—C22—C23—C24viii−178.6 (4)C10—C9—O6—Pr2173.5 (3)
C21—C22—C24—C23viii−179.6 (4)O1—Pr2—O6—C9−15.0 (3)
C23—C22—C24—C23viii−56.8 (6)O3W—Pr2—O6—C964.0 (3)
O2—C1—O1—Pr2−149.7 (4)O11—Pr2—O6—C9−153.6 (3)
C2—C1—O1—Pr231.5 (8)O8—Pr2—O6—C9−117.7 (2)
O2—C1—O1—Pr1−6.6 (3)O7—Pr2—O6—C9124.0 (3)
C2—C1—O1—Pr1174.7 (3)O4W—Pr2—O6—C9−75.8 (2)
O6—Pr2—O1—C1162.9 (5)O7ii—Pr2—O6—C9158.6 (2)
O3W—Pr2—O1—C147.9 (5)O5—Pr2—O6—C93.5 (2)
O11—Pr2—O1—C1−107.3 (5)O6—Pr2—O7—C16vi−27.6 (5)
O8—Pr2—O1—C1−50.1 (5)O1—Pr2—O7—C16vi82.4 (5)
O7—Pr2—O1—C165.5 (6)O3W—Pr2—O7—C16vi99.9 (5)
O4W—Pr2—O1—C1−131.1 (6)O11—Pr2—O7—C16vi−102.2 (5)
O7ii—Pr2—O1—C1−12.2 (6)O8—Pr2—O7—C16vi−175.4 (5)
O5—Pr2—O1—C1147.4 (6)O4W—Pr2—O7—C16vi−66.8 (6)
O6—Pr2—O1—Pr123.94 (14)O7ii—Pr2—O7—C16vi178.7 (6)
O3W—Pr2—O1—Pr1−91.06 (12)O5—Pr2—O7—C16vi14.8 (5)
O11—Pr2—O1—Pr1113.79 (13)O6—Pr2—O7—Pr2ii153.76 (12)
O8—Pr2—O1—Pr1170.96 (12)O1—Pr2—O7—Pr2ii−96.23 (14)
O7—Pr2—O1—Pr1−73.42 (15)O3W—Pr2—O7—Pr2ii−78.73 (12)
O4W—Pr2—O1—Pr189.94 (11)O11—Pr2—O7—Pr2ii79.15 (11)
O7ii—Pr2—O1—Pr1−151.11 (9)O8—Pr2—O7—Pr2ii5.93 (14)
O5—Pr2—O1—Pr18.51 (8)O4W—Pr2—O7—Pr2ii114.50 (14)
O2—Pr1—O1—C14.0 (2)O7ii—Pr2—O7—Pr2ii0.0
O3—Pr1—O1—C1140.0 (2)O5—Pr2—O7—Pr2ii−163.82 (10)
O1W—Pr1—O1—C147.3 (2)O6—Pr2—O8—C16iii−121.1 (2)
O10—Pr1—O1—C1−117.1 (2)O1—Pr2—O8—C16iii126.3 (2)
O5—Pr1—O1—C1−171.8 (2)O3W—Pr2—O8—C16iii57.5 (2)
O9—Pr1—O1—C1−91.0 (2)O11—Pr2—O8—C16iii−86.4 (2)
O2W—Pr1—O1—C1109.2 (2)O7—Pr2—O8—C16iii−13.4 (2)
O2—Pr1—O1—Pr2166.46 (18)O4W—Pr2—O8—C16iii−162.9 (2)
O3—Pr1—O1—Pr2−57.52 (15)O7ii—Pr2—O8—C16iii−6.47 (19)
O1W—Pr1—O1—Pr2−150.25 (11)O5—Pr2—O8—C16iii151.15 (19)
O10—Pr1—O1—Pr245.34 (13)O10—C17—O9—Pr14.0 (4)
O5—Pr1—O1—Pr2−9.33 (9)C18—C17—O9—Pr1−175.0 (3)
O9—Pr1—O1—Pr271.52 (12)O2—Pr1—O9—C17160.2 (2)
O2W—Pr1—O1—Pr2−88.32 (12)O3—Pr1—O9—C17−26.8 (3)
O1—C1—O2—Pr17.9 (4)O4—Pr1—O9—C1777.5 (2)
C2—C1—O2—Pr1−173.3 (3)O1W—Pr1—O9—C17119.3 (2)
O3—Pr1—O2—C1−103.7 (3)O10—Pr1—O9—C17−2.2 (2)
O4—Pr1—O2—C1143.3 (3)O5—Pr1—O9—C17−84.7 (2)
O1W—Pr1—O2—C1−139.5 (3)O2W—Pr1—O9—C17−124.3 (2)
O10—Pr1—O2—C184.6 (3)O4i—Pr1—O9—C1729.2 (2)
O5—Pr1—O2—C1−0.2 (3)O1—Pr1—O9—C17−151.1 (2)
O9—Pr1—O2—C167.0 (2)O9—C17—O10—Pr1−4.0 (4)
O2W—Pr1—O2—C1−69.0 (3)C18—C17—O10—Pr1174.9 (3)
O4i—Pr1—O2—C1−179.4 (2)O2—Pr1—O10—C17−20.2 (2)
O1—Pr1—O2—C1−4.1 (2)O3—Pr1—O10—C17164.4 (2)
O2—Pr1—O3—C8v−112.3 (2)O4—Pr1—O10—C17−82.1 (2)
O4—Pr1—O3—C8v−8.1 (2)O1W—Pr1—O10—C17−123.3 (2)
O1W—Pr1—O3—C8v−78.6 (2)O5—Pr1—O10—C1783.0 (2)
O10—Pr1—O3—C8v61.1 (2)O9—Pr1—O10—C172.2 (2)
O5—Pr1—O3—C8v135.4 (2)O2W—Pr1—O10—C17119.2 (2)
O9—Pr1—O3—C8v80.2 (2)O4i—Pr1—O10—C17−147.4 (2)
O2W—Pr1—O3—C8v−150.8 (2)O1—Pr1—O10—C1734.0 (2)
O4i—Pr1—O3—C8v−6.3 (2)O12—C21—O11—Pr231.6 (6)
O1—Pr1—O3—C8v177.54 (19)C22—C21—O11—Pr2−146.9 (3)
O2—Pr1—O4—C8iv−21.8 (5)O6—Pr2—O11—C2156.6 (3)
O3—Pr1—O4—C8iv−169.2 (5)O1—Pr2—O11—C21−47.7 (4)
O1W—Pr1—O4—C8iv−93.6 (5)O3W—Pr2—O11—C21173.9 (3)
O10—Pr1—O4—C8iv113.7 (5)O8—Pr2—O11—C21−104.4 (3)
O5—Pr1—O4—C8iv89.4 (5)O7—Pr2—O11—C21137.0 (3)
O9—Pr1—O4—C8iv60.0 (5)O4W—Pr2—O11—C21−24.7 (3)
O2W—Pr1—O4—C8iv−92.1 (5)O7ii—Pr2—O11—C21−156.1 (3)
O4i—Pr1—O4—C8iv−170.7 (6)O5—Pr2—O11—C2137.0 (3)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z; (vi) −x, −y, −z; (vii) −x+1, −y, −z+1; (viii) −x, −y, −z−1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W···O12ix0.852.042.882 (4)170
O1W—H1W···O10i0.851.902.720 (4)163
O2W—H3W···O4Wix0.851.942.786 (4)171
O3W—H5W···O90.851.972.722 (4)147
O3W—H6W···O11ii0.851.952.777 (4)166
O4W—H7W···O120.851.732.551 (4)161
O4W—H8W···O2W0.852.042.874 (4)165
Symmetry codes: (ix) −x+1, −y+1, −z; (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W···O12i0.852.042.882 (4)170
O1W—H1W···O10ii0.851.902.720 (4)163
O2W—H3W···O4Wi0.851.942.786 (4)171
O3W—H5W···O90.851.972.722 (4)147
O3W—H6W···O11iii0.851.952.777 (4)166
O4W—H7W···O120.851.732.551 (4)161
O4W—H8W···O2W0.852.042.874 (4)165
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z.
Acknowledgements top

This work was supported by the National Science Foundation of China (grant No. 20571014) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, the Ministry of Education.

references
References top

Brandenburg, K. (1998). DIAMOND. Version 2.1. Crystal Impact GbR, Bonn, Germany.

Bruker (2001). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Kurmoo, M., Kumagai, H., Akita-Tanaka, M., Inoue, K. & Takagi, S. (2006). Inorg. Chem. 45, 1627–1637.

Kurmoo, M., Kumagai, H., Hughes, S. M. & Kepert, C. J. (2003). Inorg. Chem. 42, 6709–6722.

Qi, Y. J., Wang, Y. H., Hu, C. W., Cao, M. H., Mao, L. & Wang, E. B. (2003). Inorg. Chem. 42, 8519–8523.

Rao, K. P., Thirumurugan, A. & Rao, C. N. R. (2007). Chem. Eur. J. 13, 3193–3201.

Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Yu, M., Xie, L. H., Liu, S. X., Wang, C. L., Cheng, H. Y., Ren, Y. H. & Su, Z. M. (2007). Inorg. Chim. Acta, 360, 3108–3112.