Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028437/ng2275sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028437/ng2275Isup2.hkl |
CCDC reference: 654755
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.024
- wR factor = 0.051
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O2W - H4W ... ?
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O6
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Pr1 (3) 3.16 PLAT794_ALERT_5_G Check Predicted Bond Valency for Pr2 (3) 3.19
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
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).
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.
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.
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).
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).
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).
[Pr2(C8H10O4)3(H2O)4] | Z = 2 |
Mr = 864.36 | F(000) = 856 |
Triclinic, P1 | Dx = 1.960 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.439 (2) Å | Cell parameters from 776 reflections |
b = 11.964 (2) Å | θ = 3.0–25.0° |
c = 12.343 (3) Å | µ = 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 |
Rigaku R-AXIS RAPID IP diffractometer | 5116 independent reflections |
Radiation source: fine-focus sealed tube | 4548 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 0 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ω scans | h = −13→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −14→14 |
Tmin = 0.419, Tmax = 0.443 | l = −14→14 |
11551 measured reflections |
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.051 | H-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 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.90 e Å−3 |
[Pr2(C8H10O4)3(H2O)4] | γ = 101.128 (12)° |
Mr = 864.36 | V = 1464.9 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.439 (2) Å | Mo Kα radiation |
b = 11.964 (2) Å | µ = 3.36 mm−1 |
c = 12.343 (3) Å | T = 298 K |
α = 94.794 (18)° | 0.27 × 0.26 × 0.24 mm |
β = 115.82 (3)° |
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 = 0.443 | Rint = 0.029 |
11551 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.051 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.51 e Å−3 |
5116 reflections | Δρmin = −0.90 e Å−3 |
379 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Pr1 | 0.488253 (18) | 0.430131 (16) | 0.319055 (17) | 0.01375 (6) | |
Pr2 | 0.462496 (17) | 0.167914 (16) | 0.025852 (16) | 0.01346 (6) | |
C1 | 0.7123 (3) | 0.4174 (3) | 0.2526 (3) | 0.0201 (8) | |
C2 | 0.8420 (3) | 0.4200 (3) | 0.2469 (3) | 0.0226 (8) | |
H2 | 0.8221 | 0.3692 | 0.1712 | 0.027* | |
C3 | 0.9097 (4) | 0.5418 (4) | 0.2471 (4) | 0.0360 (11) | |
H3A | 0.9243 | 0.5936 | 0.3190 | 0.043* | |
H3B | 0.8515 | 0.5679 | 0.1752 | 0.043* | |
C4 | 0.9352 (4) | 0.3750 (3) | 0.3572 (4) | 0.0244 (8) | |
H4A | 0.9435 | 0.4176 | 0.4317 | 0.029* | |
H4B | 0.8945 | 0.2939 | 0.3502 | 0.029* | |
C5 | 1.0442 (4) | 0.5469 (4) | 0.2471 (4) | 0.0404 (12) | |
H5A | 1.0292 | 0.4975 | 0.1733 | 0.048* | |
H5B | 1.0847 | 0.6257 | 0.2464 | 0.048* | |
C6 | 1.0758 (4) | 0.3865 (3) | 0.3678 (4) | 0.0226 (8) | |
H6A | 1.1335 | 0.3688 | 0.4458 | 0.027* | |
H6B | 1.0700 | 0.3301 | 0.3033 | 0.027* | |
C7 | 1.1394 (3) | 0.5078 (3) | 0.3584 (3) | 0.0191 (8) | |
H7 | 1.1609 | 0.5625 | 0.4321 | 0.023* | |
C8 | 1.2686 (3) | 0.5033 (3) | 0.3541 (3) | 0.0169 (7) | |
C9 | 0.2286 (4) | 0.2082 (3) | 0.0562 (3) | 0.0201 (8) | |
C10 | 0.0992 (3) | 0.2270 (3) | 0.0508 (4) | 0.0222 (8) | |
H10 | 0.1172 | 0.3063 | 0.0929 | 0.027* | |
C11 | 0.0512 (3) | 0.1417 (3) | 0.1181 (3) | 0.0206 (8) | |
H11A | 0.0498 | 0.0640 | 0.0873 | 0.025* | |
H11B | 0.1145 | 0.1614 | 0.2048 | 0.025* | |
C12 | −0.0075 (4) | 0.2124 (4) | −0.0817 (4) | 0.0287 (9) | |
H12A | −0.0206 | 0.1365 | −0.1262 | 0.034* | |
H12B | 0.0233 | 0.2705 | −0.1203 | 0.034* | |
C13 | −0.0887 (3) | 0.1431 (3) | 0.1022 (3) | 0.0226 (8) | |
H13A | −0.0829 | 0.2152 | 0.1489 | 0.027* | |
H13B | −0.1196 | 0.0798 | 0.1354 | 0.027* | |
C14 | −0.1411 (4) | 0.2248 (4) | −0.0888 (4) | 0.0282 (9) | |
H14A | −0.1291 | 0.3010 | −0.0455 | 0.034* | |
H14B | −0.2066 | 0.2169 | −0.1738 | 0.034* | |
C15 | −0.1914 (3) | 0.1317 (3) | −0.0317 (3) | 0.0170 (7) | |
H15 | −0.2029 | 0.0556 | −0.0767 | 0.020* | |
C16 | −0.3234 (3) | 0.1365 (3) | −0.0334 (3) | 0.0175 (8) | |
C17 | 0.4813 (4) | 0.2186 (3) | 0.4184 (3) | 0.0242 (9) | |
C18 | 0.4814 (5) | 0.1149 (3) | 0.4800 (4) | 0.0323 (10) | |
H18 | 0.4469 | 0.1289 | 0.5387 | 0.039* | |
C19 | 0.6205 (5) | 0.0967 (4) | 0.5510 (4) | 0.0467 (12) | |
H19A | 0.6786 | 0.1656 | 0.6125 | 0.056* | |
H19B | 0.6582 | 0.0841 | 0.4957 | 0.056* | |
C20 | 0.3862 (5) | 0.0083 (4) | 0.3863 (4) | 0.0440 (12) | |
H20A | 0.4165 | −0.0071 | 0.3257 | 0.053* | |
H20B | 0.2973 | 0.0213 | 0.3445 | 0.053* | |
C21 | 0.2456 (4) | 0.1272 (3) | −0.2847 (3) | 0.0220 (8) | |
C22 | 0.1333 (4) | 0.0380 (3) | −0.3917 (3) | 0.0273 (9) | |
H22 | 0.1574 | −0.0363 | −0.3880 | 0.033* | |
C23 | 0.0041 (5) | 0.0232 (5) | −0.3810 (4) | 0.0489 (13) | |
H23A | −0.0200 | 0.0966 | −0.3819 | 0.059* | |
H23B | 0.0181 | 0.0004 | −0.3035 | 0.059* | |
C24 | 0.1101 (5) | 0.0684 (5) | −0.5141 (4) | 0.0491 (13) | |
H24A | 0.1917 | 0.0748 | −0.5222 | 0.059* | |
H24B | 0.0887 | 0.1430 | −0.5187 | 0.059* | |
O1 | 0.6014 (2) | 0.3505 (2) | 0.1740 (2) | 0.0260 (6) | |
O2 | 0.7147 (3) | 0.4855 (2) | 0.3370 (3) | 0.0353 (7) | |
O3 | 0.2670 (2) | 0.4772 (2) | 0.2521 (2) | 0.0271 (6) | |
O4 | 0.6233 (2) | 0.4813 (2) | 0.5478 (2) | 0.0222 (6) | |
O5 | 0.3421 (2) | 0.2627 (2) | 0.1422 (2) | 0.0251 (6) | |
O6 | 0.2228 (3) | 0.1361 (2) | −0.0272 (3) | 0.0350 (7) | |
O7 | 0.3943 (2) | −0.0465 (2) | 0.0225 (2) | 0.0223 (6) | |
O8 | 0.6411 (3) | 0.2292 (2) | −0.0383 (2) | 0.0250 (6) | |
O9 | 0.5688 (3) | 0.2502 (2) | 0.3825 (3) | 0.0291 (6) | |
O10 | 0.3942 (3) | 0.2739 (2) | 0.4051 (2) | 0.0242 (6) | |
O11 | 0.3319 (3) | 0.0925 (2) | −0.1981 (2) | 0.0242 (6) | |
O12 | 0.2456 (3) | 0.2317 (2) | −0.2863 (2) | 0.0333 (7) | |
O1W | 0.5733 (3) | 0.6472 (2) | 0.3677 (2) | 0.0289 (6) | |
H1W | 0.5998 | 0.6778 | 0.4418 | 0.035* | |
H2W | 0.6316 | 0.6758 | 0.3456 | 0.035* | |
O2W | 0.4036 (3) | 0.5128 (2) | 0.1098 (2) | 0.0301 (6) | |
H3W | 0.4583 | 0.5631 | 0.0980 | 0.036* | |
H4W | 0.3428 | 0.5457 | 0.1062 | 0.036* | |
O3W | 0.6203 (3) | 0.1250 (2) | 0.2213 (2) | 0.0406 (8) | |
H5W | 0.6340 | 0.1582 | 0.2909 | 0.049* | |
H6W | 0.6368 | 0.0589 | 0.2269 | 0.049* | |
O4W | 0.4041 (3) | 0.3423 (2) | −0.0683 (2) | 0.0238 (6) | |
H7W | 0.3485 | 0.3204 | −0.1440 | 0.029* | |
H8W | 0.3895 | 0.3857 | −0.0200 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pr1 | 0.01010 (10) | 0.01528 (10) | 0.01643 (11) | 0.00264 (8) | 0.00685 (8) | 0.00308 (8) |
Pr2 | 0.00806 (10) | 0.01611 (11) | 0.01489 (11) | 0.00227 (8) | 0.00499 (8) | −0.00001 (8) |
C1 | 0.0129 (18) | 0.0218 (19) | 0.021 (2) | 0.0011 (16) | 0.0051 (16) | 0.0039 (16) |
C2 | 0.0127 (18) | 0.033 (2) | 0.021 (2) | 0.0034 (17) | 0.0091 (16) | −0.0012 (16) |
C3 | 0.018 (2) | 0.045 (3) | 0.058 (3) | 0.018 (2) | 0.022 (2) | 0.032 (2) |
C4 | 0.0162 (19) | 0.023 (2) | 0.033 (2) | 0.0020 (17) | 0.0118 (18) | 0.0056 (17) |
C5 | 0.022 (2) | 0.063 (3) | 0.055 (3) | 0.023 (2) | 0.024 (2) | 0.043 (3) |
C6 | 0.0137 (18) | 0.025 (2) | 0.029 (2) | 0.0056 (16) | 0.0093 (17) | 0.0049 (17) |
C7 | 0.0117 (18) | 0.0210 (19) | 0.027 (2) | 0.0048 (15) | 0.0107 (16) | 0.0029 (15) |
C8 | 0.0105 (18) | 0.0137 (17) | 0.026 (2) | 0.0021 (15) | 0.0082 (17) | 0.0032 (15) |
C9 | 0.0144 (19) | 0.0145 (18) | 0.031 (2) | 0.0001 (16) | 0.0117 (18) | 0.0055 (16) |
C10 | 0.0111 (18) | 0.0197 (19) | 0.035 (2) | 0.0019 (16) | 0.0123 (17) | −0.0006 (16) |
C11 | 0.0141 (18) | 0.028 (2) | 0.0193 (19) | 0.0080 (16) | 0.0070 (16) | 0.0009 (16) |
C12 | 0.019 (2) | 0.041 (2) | 0.038 (2) | 0.0105 (19) | 0.0202 (19) | 0.022 (2) |
C13 | 0.0158 (19) | 0.031 (2) | 0.022 (2) | 0.0060 (17) | 0.0100 (17) | 0.0039 (16) |
C14 | 0.0145 (19) | 0.038 (2) | 0.038 (2) | 0.0088 (18) | 0.0143 (19) | 0.0211 (19) |
C15 | 0.0125 (17) | 0.0184 (18) | 0.022 (2) | 0.0033 (15) | 0.0102 (16) | 0.0030 (15) |
C16 | 0.0129 (18) | 0.023 (2) | 0.0152 (18) | 0.0029 (16) | 0.0069 (15) | 0.0004 (15) |
C17 | 0.035 (2) | 0.0175 (19) | 0.019 (2) | 0.0034 (18) | 0.0133 (18) | 0.0015 (15) |
C18 | 0.048 (3) | 0.022 (2) | 0.037 (3) | 0.015 (2) | 0.025 (2) | 0.0127 (18) |
C19 | 0.048 (3) | 0.026 (2) | 0.041 (3) | −0.007 (2) | 0.004 (2) | 0.013 (2) |
C20 | 0.043 (3) | 0.032 (2) | 0.040 (3) | 0.001 (2) | 0.005 (2) | 0.019 (2) |
C21 | 0.019 (2) | 0.024 (2) | 0.019 (2) | 0.0024 (17) | 0.0078 (17) | 0.0016 (16) |
C22 | 0.023 (2) | 0.022 (2) | 0.023 (2) | 0.0067 (18) | −0.0003 (17) | −0.0024 (16) |
C23 | 0.035 (3) | 0.072 (4) | 0.018 (2) | −0.015 (3) | 0.008 (2) | −0.005 (2) |
C24 | 0.032 (3) | 0.071 (4) | 0.025 (2) | −0.019 (2) | 0.012 (2) | −0.007 (2) |
O1 | 0.0141 (13) | 0.0260 (14) | 0.0273 (15) | −0.0042 (12) | 0.0051 (12) | −0.0017 (12) |
O2 | 0.0206 (15) | 0.0397 (17) | 0.0434 (18) | 0.0003 (13) | 0.0197 (14) | −0.0140 (14) |
O3 | 0.0164 (13) | 0.0446 (17) | 0.0224 (15) | 0.0104 (13) | 0.0106 (12) | 0.0020 (12) |
O4 | 0.0118 (13) | 0.0282 (14) | 0.0225 (14) | 0.0060 (11) | 0.0043 (12) | 0.0032 (11) |
O5 | 0.0131 (13) | 0.0353 (16) | 0.0244 (15) | 0.0034 (12) | 0.0084 (12) | 0.0017 (12) |
O6 | 0.0128 (14) | 0.0319 (16) | 0.0513 (19) | −0.0004 (12) | 0.0134 (14) | −0.0151 (14) |
O7 | 0.0172 (13) | 0.0217 (14) | 0.0327 (16) | 0.0043 (12) | 0.0158 (12) | 0.0064 (11) |
O8 | 0.0199 (14) | 0.0232 (14) | 0.0402 (17) | 0.0076 (12) | 0.0201 (13) | 0.0068 (12) |
O9 | 0.0427 (17) | 0.0249 (14) | 0.0368 (17) | 0.0188 (14) | 0.0280 (15) | 0.0143 (12) |
O10 | 0.0315 (15) | 0.0195 (13) | 0.0281 (15) | 0.0088 (13) | 0.0181 (13) | 0.0066 (11) |
O11 | 0.0216 (14) | 0.0284 (14) | 0.0173 (14) | 0.0105 (12) | 0.0030 (12) | 0.0017 (11) |
O12 | 0.0361 (17) | 0.0226 (15) | 0.0232 (15) | 0.0028 (13) | −0.0003 (13) | 0.0040 (12) |
O1W | 0.0431 (17) | 0.0210 (14) | 0.0289 (16) | 0.0029 (13) | 0.0248 (14) | 0.0016 (12) |
O2W | 0.0356 (16) | 0.0315 (15) | 0.0332 (16) | 0.0112 (14) | 0.0223 (14) | 0.0142 (13) |
O3W | 0.061 (2) | 0.0359 (17) | 0.0158 (15) | 0.0285 (16) | 0.0040 (15) | 0.0004 (12) |
O4W | 0.0281 (15) | 0.0207 (13) | 0.0180 (14) | 0.0050 (12) | 0.0079 (12) | −0.0009 (11) |
Pr1—O2 | 2.451 (3) | C11—H11A | 0.9700 |
Pr1—O3 | 2.493 (2) | C11—H11B | 0.9700 |
Pr1—O4 | 2.506 (3) | C12—C14 | 1.529 (5) |
Pr1—O1W | 2.511 (3) | C12—H12A | 0.9700 |
Pr1—O10 | 2.516 (3) | C12—H12B | 0.9700 |
Pr1—O5 | 2.524 (3) | C13—C15 | 1.530 (5) |
Pr1—O9 | 2.552 (3) | C13—H13A | 0.9700 |
Pr1—O2W | 2.684 (3) | C13—H13B | 0.9700 |
Pr1—O4i | 2.740 (2) | C14—C15 | 1.519 (5) |
Pr1—O1 | 2.828 (3) | C14—H14A | 0.9700 |
Pr2—O6 | 2.466 (3) | C14—H14B | 0.9700 |
Pr2—O1 | 2.471 (3) | C15—C16 | 1.513 (4) |
Pr2—O3W | 2.472 (3) | C15—H15 | 0.9800 |
Pr2—O11 | 2.481 (3) | C16—O8v | 1.250 (4) |
Pr2—O8 | 2.503 (2) | C16—O7vi | 1.271 (4) |
Pr2—O7 | 2.525 (3) | C17—O10 | 1.261 (4) |
Pr2—O4W | 2.533 (2) | C17—O9 | 1.269 (5) |
Pr2—O7ii | 2.602 (2) | C17—C18 | 1.507 (5) |
Pr2—O5 | 2.702 (2) | C18—C20 | 1.507 (6) |
C1—O2 | 1.255 (4) | C18—C19 | 1.516 (6) |
C1—O1 | 1.263 (4) | C18—H18 | 0.9800 |
C1—C2 | 1.510 (5) | C19—C20vii | 1.535 (6) |
C2—C3 | 1.511 (6) | C19—H19A | 0.9700 |
C2—C4 | 1.537 (5) | C19—H19B | 0.9700 |
C2—H2 | 0.9800 | C20—C19vii | 1.535 (6) |
C3—C5 | 1.527 (5) | C20—H20A | 0.9700 |
C3—H3A | 0.9700 | C20—H20B | 0.9700 |
C3—H3B | 0.9700 | C21—O12 | 1.252 (4) |
C4—C6 | 1.534 (5) | C21—O11 | 1.266 (4) |
C4—H4A | 0.9700 | C21—C22 | 1.513 (5) |
C4—H4B | 0.9700 | C22—C24 | 1.505 (6) |
C5—C7 | 1.514 (5) | C22—C23 | 1.519 (6) |
C5—H5A | 0.9700 | C22—H22 | 0.9800 |
C5—H5B | 0.9700 | C23—C24viii | 1.523 (6) |
C6—C7 | 1.530 (5) | C23—H23A | 0.9700 |
C6—H6A | 0.9700 | C23—H23B | 0.9700 |
C6—H6B | 0.9700 | C24—C23viii | 1.523 (6) |
C7—C8 | 1.513 (4) | C24—H24A | 0.9700 |
C7—H7 | 0.9800 | C24—H24B | 0.9700 |
C8—O3iii | 1.262 (4) | O1W—H1W | 0.8500 |
C8—O4iv | 1.264 (4) | O1W—H2W | 0.8500 |
C9—O6 | 1.257 (4) | O2W—H3W | 0.8499 |
C9—O5 | 1.263 (4) | O2W—H4W | 0.8501 |
C9—C10 | 1.513 (5) | O3W—H5W | 0.8499 |
C10—C12 | 1.525 (5) | O3W—H6W | 0.8500 |
C10—C11 | 1.535 (5) | O4W—H7W | 0.8500 |
C10—H10 | 0.9800 | O4W—H8W | 0.8500 |
C11—C13 | 1.528 (5) | ||
O2—Pr1—O3 | 146.79 (10) | C6—C7—H7 | 108.8 |
O2—Pr1—O4 | 80.40 (9) | O3iii—C8—O4iv | 119.7 (3) |
O3—Pr1—O4 | 110.50 (8) | O3iii—C8—C7 | 119.7 (3) |
O2—Pr1—O1W | 70.10 (9) | O4iv—C8—C7 | 120.5 (3) |
O3—Pr1—O1W | 82.36 (9) | O6—C9—O5 | 119.1 (3) |
O4—Pr1—O1W | 74.75 (9) | O6—C9—C10 | 119.0 (3) |
O2—Pr1—O10 | 128.45 (10) | O5—C9—C10 | 121.9 (3) |
O3—Pr1—O10 | 84.50 (9) | C9—C10—C12 | 110.8 (3) |
O4—Pr1—O10 | 72.71 (9) | C9—C10—C11 | 109.0 (3) |
O1W—Pr1—O10 | 137.74 (8) | C12—C10—C11 | 111.2 (3) |
O2—Pr1—O5 | 110.28 (8) | C9—C10—H10 | 108.6 |
O3—Pr1—O5 | 80.23 (9) | C12—C10—H10 | 108.6 |
O4—Pr1—O5 | 143.25 (8) | C11—C10—H10 | 108.6 |
O1W—Pr1—O5 | 141.92 (9) | C13—C11—C10 | 112.6 (3) |
O10—Pr1—O5 | 73.60 (8) | C13—C11—H11A | 109.1 |
O2—Pr1—O9 | 79.70 (10) | C10—C11—H11A | 109.1 |
O3—Pr1—O9 | 132.96 (9) | C13—C11—H11B | 109.1 |
O4—Pr1—O9 | 74.98 (9) | C10—C11—H11B | 109.1 |
O1W—Pr1—O9 | 140.08 (10) | H11A—C11—H11B | 107.8 |
O10—Pr1—O9 | 51.45 (8) | C10—C12—C14 | 111.4 (3) |
O5—Pr1—O9 | 72.78 (9) | C10—C12—H12A | 109.3 |
O2—Pr1—O2W | 87.07 (10) | C14—C12—H12A | 109.3 |
O3—Pr1—O2W | 65.97 (9) | C10—C12—H12B | 109.3 |
O4—Pr1—O2W | 145.39 (8) | C14—C12—H12B | 109.3 |
O1W—Pr1—O2W | 70.65 (9) | H12A—C12—H12B | 108.0 |
O10—Pr1—O2W | 137.12 (9) | C11—C13—C15 | 112.9 (3) |
O5—Pr1—O2W | 71.35 (9) | C11—C13—H13A | 109.0 |
O9—Pr1—O2W | 134.29 (8) | C15—C13—H13A | 109.0 |
O2—Pr1—O4i | 131.45 (8) | C11—C13—H13B | 109.0 |
O3—Pr1—O4i | 49.08 (8) | C15—C13—H13B | 109.0 |
O4—Pr1—O4i | 61.45 (9) | H13A—C13—H13B | 107.8 |
O1W—Pr1—O4i | 71.63 (8) | C15—C14—C12 | 109.3 (3) |
O10—Pr1—O4i | 69.45 (8) | C15—C14—H14A | 109.8 |
O5—Pr1—O4i | 118.26 (8) | C12—C14—H14A | 109.8 |
O9—Pr1—O4i | 114.39 (8) | C15—C14—H14B | 109.8 |
O2W—Pr1—O4i | 107.14 (8) | C12—C14—H14B | 109.8 |
O2—Pr1—O1 | 47.90 (8) | H14A—C14—H14B | 108.3 |
O3—Pr1—O1 | 128.93 (8) | C16—C15—C14 | 113.7 (3) |
O4—Pr1—O1 | 120.33 (8) | C16—C15—C13 | 107.2 (3) |
O1W—Pr1—O1 | 105.56 (8) | C14—C15—C13 | 110.2 (3) |
O10—Pr1—O1 | 113.86 (8) | C16—C15—H15 | 108.5 |
O5—Pr1—O1 | 62.49 (8) | C14—C15—H15 | 108.5 |
O9—Pr1—O1 | 69.17 (8) | C13—C15—H15 | 108.5 |
O2W—Pr1—O1 | 69.60 (8) | O8v—C16—O7vi | 120.1 (3) |
O4i—Pr1—O1 | 176.43 (7) | O8v—C16—C15 | 120.7 (3) |
O6—Pr2—O1 | 112.17 (9) | O7vi—C16—C15 | 119.1 (3) |
O6—Pr2—O3W | 119.77 (11) | O10—C17—O9 | 120.9 (3) |
O1—Pr2—O3W | 70.03 (10) | O10—C17—C18 | 118.7 (3) |
O6—Pr2—O11 | 72.91 (9) | O9—C17—C18 | 120.4 (4) |
O1—Pr2—O11 | 140.80 (9) | C20—C18—C17 | 109.7 (3) |
O3W—Pr2—O11 | 143.49 (8) | C20—C18—C19 | 111.4 (4) |
O6—Pr2—O8 | 146.90 (10) | C17—C18—C19 | 113.1 (4) |
O1—Pr2—O8 | 78.18 (9) | C20—C18—H18 | 107.5 |
O3W—Pr2—O8 | 93.32 (10) | C17—C18—H18 | 107.5 |
O11—Pr2—O8 | 79.83 (9) | C19—C18—H18 | 107.5 |
O6—Pr2—O7 | 77.83 (9) | C18—C19—C20vii | 110.5 (4) |
O1—Pr2—O7 | 139.66 (9) | C18—C19—H19A | 109.6 |
O3W—Pr2—O7 | 71.37 (9) | C20vii—C19—H19A | 109.6 |
O11—Pr2—O7 | 79.35 (9) | C18—C19—H19B | 109.6 |
O8—Pr2—O7 | 115.48 (8) | C20vii—C19—H19B | 109.6 |
O6—Pr2—O4W | 77.50 (9) | H19A—C19—H19B | 108.1 |
O1—Pr2—O4W | 69.00 (9) | C18—C20—C19vii | 110.2 (4) |
O3W—Pr2—O4W | 139.02 (9) | C18—C20—H20A | 109.6 |
O11—Pr2—O4W | 74.81 (8) | C19vii—C20—H20A | 109.6 |
O8—Pr2—O4W | 77.52 (8) | C18—C20—H20B | 109.6 |
O7—Pr2—O4W | 148.44 (8) | C19vii—C20—H20B | 109.6 |
O6—Pr2—O7ii | 135.00 (8) | H20A—C20—H20B | 108.1 |
O1—Pr2—O7ii | 112.57 (8) | O12—C21—O11 | 123.8 (3) |
O3W—Pr2—O7ii | 72.41 (9) | O12—C21—C22 | 117.4 (3) |
O11—Pr2—O7ii | 75.79 (8) | O11—C21—C22 | 118.7 (3) |
O8—Pr2—O7ii | 50.64 (8) | C24—C22—C21 | 113.1 (4) |
O7—Pr2—O7ii | 65.17 (9) | C24—C22—C23 | 109.5 (3) |
O4W—Pr2—O7ii | 123.70 (8) | C21—C22—C23 | 109.8 (3) |
O6—Pr2—O5 | 49.44 (8) | C24—C22—H22 | 108.1 |
O1—Pr2—O5 | 65.04 (8) | C21—C22—H22 | 108.1 |
O3W—Pr2—O5 | 89.86 (9) | C23—C22—H22 | 108.1 |
O11—Pr2—O5 | 118.55 (8) | C22—C23—C24viii | 111.1 (4) |
O8—Pr2—O5 | 139.43 (8) | C22—C23—H23A | 109.4 |
O7—Pr2—O5 | 103.84 (8) | C24viii—C23—H23A | 109.4 |
O4W—Pr2—O5 | 73.90 (8) | C22—C23—H23B | 109.4 |
O7ii—Pr2—O5 | 161.22 (8) | C24viii—C23—H23B | 109.4 |
O2—C1—O1 | 119.1 (3) | H23A—C23—H23B | 108.0 |
O2—C1—C2 | 118.7 (3) | C22—C24—C23viii | 111.3 (4) |
O1—C1—C2 | 122.2 (3) | C22—C24—H24A | 109.4 |
C1—C2—C3 | 110.6 (3) | C23viii—C24—H24A | 109.4 |
C1—C2—C4 | 109.2 (3) | C22—C24—H24B | 109.4 |
C3—C2—C4 | 110.2 (3) | C23viii—C24—H24B | 109.4 |
C1—C2—H2 | 108.9 | H24A—C24—H24B | 108.0 |
C3—C2—H2 | 108.9 | C1—O1—Pr2 | 152.8 (2) |
C4—C2—H2 | 108.9 | C1—O1—Pr1 | 87.1 (2) |
C2—C3—C5 | 111.3 (3) | Pr2—O1—Pr1 | 114.27 (9) |
C2—C3—H3A | 109.4 | C1—O2—Pr1 | 105.5 (2) |
C5—C3—H3A | 109.4 | C8v—O3—Pr1 | 100.9 (2) |
C2—C3—H3B | 109.4 | C8iv—O4—Pr1 | 152.0 (2) |
C5—C3—H3B | 109.4 | C8iv—O4—Pr1i | 89.1 (2) |
H3A—C3—H3B | 108.0 | Pr1—O4—Pr1i | 118.55 (9) |
C6—C4—C2 | 113.3 (3) | C9—O5—Pr1 | 150.7 (2) |
C6—C4—H4A | 108.9 | C9—O5—Pr2 | 89.8 (2) |
C2—C4—H4A | 108.9 | Pr1—O5—Pr2 | 116.90 (9) |
C6—C4—H4B | 108.9 | C9—O6—Pr2 | 101.3 (2) |
C2—C4—H4B | 108.9 | C16vi—O7—Pr2 | 153.8 (2) |
H4A—C4—H4B | 107.7 | C16vi—O7—Pr2ii | 91.35 (19) |
C7—C5—C3 | 111.4 (3) | Pr2—O7—Pr2ii | 114.83 (9) |
C7—C5—H5A | 109.3 | C16iii—O8—Pr2 | 96.6 (2) |
C3—C5—H5A | 109.3 | C17—O9—Pr1 | 92.8 (2) |
C7—C5—H5B | 109.3 | C17—O10—Pr1 | 94.7 (2) |
C3—C5—H5B | 109.3 | C21—O11—Pr2 | 132.8 (2) |
H5A—C5—H5B | 108.0 | Pr1—O1W—H1W | 114.7 |
C7—C6—C4 | 112.8 (3) | Pr1—O1W—H2W | 116.7 |
C7—C6—H6A | 109.0 | H1W—O1W—H2W | 109.1 |
C4—C6—H6A | 109.0 | Pr1—O2W—H3W | 120.1 |
C7—C6—H6B | 109.0 | Pr1—O2W—H4W | 107.1 |
C4—C6—H6B | 109.0 | H3W—O2W—H4W | 104.8 |
H6A—C6—H6B | 107.8 | Pr2—O3W—H5W | 123.1 |
C8—C7—C5 | 111.8 (3) | Pr2—O3W—H6W | 122.1 |
C8—C7—C6 | 107.4 (3) | H5W—O3W—H6W | 109.1 |
C5—C7—C6 | 111.2 (3) | Pr2—O4W—H7W | 109.8 |
C8—C7—H7 | 108.8 | Pr2—O4W—H8W | 108.2 |
C5—C7—H7 | 108.8 | H7W—O4W—H8W | 121.8 |
O2—C1—C2—C3 | −53.6 (5) | O1—Pr1—O4—C8iv | 5.7 (5) |
O1—C1—C2—C3 | 125.1 (4) | O2—Pr1—O4—Pr1i | 148.93 (12) |
O2—C1—C2—C4 | 67.8 (4) | O3—Pr1—O4—Pr1i | 1.51 (13) |
O1—C1—C2—C4 | −113.5 (4) | O1W—Pr1—O4—Pr1i | 77.09 (11) |
C1—C2—C3—C5 | 177.5 (3) | O10—Pr1—O4—Pr1i | −75.57 (11) |
C4—C2—C3—C5 | 56.6 (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—Pr1i | 78.59 (16) |
C2—C3—C5—C7 | −59.6 (5) | O4i—Pr1—O4—Pr1i | 0.0 |
C2—C4—C6—C7 | 49.4 (4) | O1—Pr1—O4—Pr1i | 176.45 (8) |
C3—C5—C7—C8 | 175.4 (4) | O6—C9—O5—Pr1 | 162.5 (3) |
C3—C5—C7—C6 | 55.4 (5) | C10—C9—O5—Pr1 | −17.6 (7) |
C4—C6—C7—C8 | −173.0 (3) | O6—C9—O5—Pr2 | 5.9 (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—O3iii | 89.6 (4) | O3—Pr1—O5—C9 | −0.9 (5) |
C5—C7—C8—O4iv | 151.6 (4) | O4—Pr1—O5—C9 | 110.4 (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—C9 | 86.2 (5) |
O5—C9—C10—C12 | 147.0 (4) | O9—Pr1—O5—C9 | 140.1 (5) |
O6—C9—C10—C11 | 89.6 (4) | O2W—Pr1—O5—C9 | −68.7 (5) |
O5—C9—C10—C11 | −90.3 (4) | O4i—Pr1—O5—C9 | 31.2 (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—Pr2 | 5.38 (14) |
C9—C10—C12—C14 | 177.0 (3) | O3—Pr1—O5—Pr2 | 152.67 (12) |
C11—C10—C12—C14 | 55.5 (4) | O4—Pr1—O5—Pr2 | −96.01 (14) |
C10—C11—C13—C15 | 49.9 (4) | O1W—Pr1—O5—Pr2 | 88.67 (15) |
C10—C12—C14—C15 | −60.7 (4) | O10—Pr1—O5—Pr2 | −120.24 (12) |
C12—C14—C15—C16 | 179.7 (3) | O9—Pr1—O5—Pr2 | −66.31 (11) |
C12—C14—C15—C13 | 59.3 (4) | O2W—Pr1—O5—Pr2 | 84.88 (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—Pr2 | 8.71 (9) |
C14—C15—C16—O8v | −24.5 (5) | O6—Pr2—O5—C9 | −3.5 (2) |
C13—C15—C16—O8v | 97.6 (4) | O1—Pr2—O5—C9 | 157.6 (2) |
C14—C15—C16—O7vi | 159.5 (3) | O3W—Pr2—O5—C9 | −134.4 (2) |
C13—C15—C16—O7vi | −78.4 (4) | O11—Pr2—O5—C9 | 21.6 (2) |
O10—C17—C18—C20 | 86.4 (5) | O8—Pr2—O5—C9 | 130.6 (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—C9 | 83.7 (2) |
O9—C17—C18—C19 | 30.3 (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—C20vii | 178.8 (4) | O1—Pr2—O5—Pr1 | −9.76 (10) |
C17—C18—C20—C19vii | −177.0 (4) | O3W—Pr2—O5—Pr1 | 58.18 (12) |
C19—C18—C20—C19vii | 57.1 (6) | O11—Pr2—O5—Pr1 | −145.81 (10) |
O12—C21—C22—C24 | 47.3 (5) | O8—Pr2—O5—Pr1 | −36.76 (18) |
O11—C21—C22—C24 | −134.1 (4) | O7—Pr2—O5—Pr1 | 128.93 (11) |
O12—C21—C22—C23 | −75.4 (5) | O4W—Pr2—O5—Pr1 | −83.68 (12) |
O11—C21—C22—C23 | 103.3 (4) | O7ii—Pr2—O5—Pr1 | 77.2 (3) |
C24—C22—C23—C24viii | 56.7 (6) | O5—C9—O6—Pr2 | −6.6 (4) |
C21—C22—C23—C24viii | −178.6 (4) | C10—C9—O6—Pr2 | 173.5 (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—C9 | 64.0 (3) |
O2—C1—O1—Pr2 | −149.7 (4) | O11—Pr2—O6—C9 | −153.6 (3) |
C2—C1—O1—Pr2 | 31.5 (8) | O8—Pr2—O6—C9 | −117.7 (2) |
O2—C1—O1—Pr1 | −6.6 (3) | O7—Pr2—O6—C9 | 124.0 (3) |
C2—C1—O1—Pr1 | 174.7 (3) | O4W—Pr2—O6—C9 | −75.8 (2) |
O6—Pr2—O1—C1 | 162.9 (5) | O7ii—Pr2—O6—C9 | 158.6 (2) |
O3W—Pr2—O1—C1 | 47.9 (5) | O5—Pr2—O6—C9 | 3.5 (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—C16vi | 82.4 (5) |
O7—Pr2—O1—C1 | 65.5 (6) | O3W—Pr2—O7—C16vi | 99.9 (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—C1 | 147.4 (6) | O4W—Pr2—O7—C16vi | −66.8 (6) |
O6—Pr2—O1—Pr1 | 23.94 (14) | O7ii—Pr2—O7—C16vi | 178.7 (6) |
O3W—Pr2—O1—Pr1 | −91.06 (12) | O5—Pr2—O7—C16vi | 14.8 (5) |
O11—Pr2—O1—Pr1 | 113.79 (13) | O6—Pr2—O7—Pr2ii | 153.76 (12) |
O8—Pr2—O1—Pr1 | 170.96 (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—Pr1 | 89.94 (11) | O11—Pr2—O7—Pr2ii | 79.15 (11) |
O7ii—Pr2—O1—Pr1 | −151.11 (9) | O8—Pr2—O7—Pr2ii | 5.93 (14) |
O5—Pr2—O1—Pr1 | 8.51 (8) | O4W—Pr2—O7—Pr2ii | 114.50 (14) |
O2—Pr1—O1—C1 | 4.0 (2) | O7ii—Pr2—O7—Pr2ii | 0.0 |
O3—Pr1—O1—C1 | 140.0 (2) | O5—Pr2—O7—Pr2ii | −163.82 (10) |
O1W—Pr1—O1—C1 | 47.3 (2) | O6—Pr2—O8—C16iii | −121.1 (2) |
O10—Pr1—O1—C1 | −117.1 (2) | O1—Pr2—O8—C16iii | 126.3 (2) |
O5—Pr1—O1—C1 | −171.8 (2) | O3W—Pr2—O8—C16iii | 57.5 (2) |
O9—Pr1—O1—C1 | −91.0 (2) | O11—Pr2—O8—C16iii | −86.4 (2) |
O2W—Pr1—O1—C1 | 109.2 (2) | O7—Pr2—O8—C16iii | −13.4 (2) |
O2—Pr1—O1—Pr2 | 166.46 (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—C16iii | 151.15 (19) |
O10—Pr1—O1—Pr2 | 45.34 (13) | O10—C17—O9—Pr1 | 4.0 (4) |
O5—Pr1—O1—Pr2 | −9.33 (9) | C18—C17—O9—Pr1 | −175.0 (3) |
O9—Pr1—O1—Pr2 | 71.52 (12) | O2—Pr1—O9—C17 | 160.2 (2) |
O2W—Pr1—O1—Pr2 | −88.32 (12) | O3—Pr1—O9—C17 | −26.8 (3) |
O1—C1—O2—Pr1 | 7.9 (4) | O4—Pr1—O9—C17 | 77.5 (2) |
C2—C1—O2—Pr1 | −173.3 (3) | O1W—Pr1—O9—C17 | 119.3 (2) |
O3—Pr1—O2—C1 | −103.7 (3) | O10—Pr1—O9—C17 | −2.2 (2) |
O4—Pr1—O2—C1 | 143.3 (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—C1 | 84.6 (3) | O4i—Pr1—O9—C17 | 29.2 (2) |
O5—Pr1—O2—C1 | −0.2 (3) | O1—Pr1—O9—C17 | −151.1 (2) |
O9—Pr1—O2—C1 | 67.0 (2) | O9—C17—O10—Pr1 | −4.0 (4) |
O2W—Pr1—O2—C1 | −69.0 (3) | C18—C17—O10—Pr1 | 174.9 (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—C17 | 164.4 (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—C17 | 83.0 (2) |
O10—Pr1—O3—C8v | 61.1 (2) | O9—Pr1—O10—C17 | 2.2 (2) |
O5—Pr1—O3—C8v | 135.4 (2) | O2W—Pr1—O10—C17 | 119.2 (2) |
O9—Pr1—O3—C8v | 80.2 (2) | O4i—Pr1—O10—C17 | −147.4 (2) |
O2W—Pr1—O3—C8v | −150.8 (2) | O1—Pr1—O10—C17 | 34.0 (2) |
O4i—Pr1—O3—C8v | −6.3 (2) | O12—C21—O11—Pr2 | 31.6 (6) |
O1—Pr1—O3—C8v | 177.54 (19) | C22—C21—O11—Pr2 | −146.9 (3) |
O2—Pr1—O4—C8iv | −21.8 (5) | O6—Pr2—O11—C21 | 56.6 (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—C21 | 173.9 (3) |
O10—Pr1—O4—C8iv | 113.7 (5) | O8—Pr2—O11—C21 | −104.4 (3) |
O5—Pr1—O4—C8iv | 89.4 (5) | O7—Pr2—O11—C21 | 137.0 (3) |
O9—Pr1—O4—C8iv | 60.0 (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—C21 | 37.0 (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···O12ix | 0.85 | 2.04 | 2.882 (4) | 170 |
O1W—H1W···O10i | 0.85 | 1.90 | 2.720 (4) | 163 |
O2W—H3W···O4Wix | 0.85 | 1.94 | 2.786 (4) | 171 |
O3W—H5W···O9 | 0.85 | 1.97 | 2.722 (4) | 147 |
O3W—H6W···O11ii | 0.85 | 1.95 | 2.777 (4) | 166 |
O4W—H7W···O12 | 0.85 | 1.73 | 2.551 (4) | 161 |
O4W—H8W···O2W | 0.85 | 2.04 | 2.874 (4) | 165 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z; (ix) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Pr2(C8H10O4)3(H2O)4] |
Mr | 864.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 11.439 (2), 11.964 (2), 12.343 (3) |
α, β, γ (°) | 94.794 (18), 115.82 (3), 101.128 (12) |
V (Å3) | 1464.9 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 3.36 |
Crystal size (mm) | 0.27 × 0.26 × 0.24 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.419, 0.443 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11551, 5116, 4548 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.051, 1.08 |
No. of reflections | 5116 |
No. of parameters | 379 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.51, −0.90 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···O12i | 0.85 | 2.04 | 2.882 (4) | 169.6 |
O1W—H1W···O10ii | 0.85 | 1.90 | 2.720 (4) | 163.2 |
O2W—H3W···O4Wi | 0.85 | 1.94 | 2.786 (4) | 170.8 |
O3W—H5W···O9 | 0.85 | 1.97 | 2.722 (4) | 146.7 |
O3W—H6W···O11iii | 0.85 | 1.95 | 2.777 (4) | 165.7 |
O4W—H7W···O12 | 0.85 | 1.73 | 2.551 (4) | 160.7 |
O4W—H8W···O2W | 0.85 | 2.04 | 2.874 (4) | 165.4 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z. |
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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).