Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017981/tk6081sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017981/tk6081Isup2.hkl |
CCDC reference: 200720
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.014 Å Some non-H atoms missing
- R factor = 0.057
- wR factor = 0.181
- Data-to-parameter ratio = 21.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
ABSMU_01 Alert A The ratio of given/expected absorption coefficient lies outside the range 0.90 <> 1.10 Calculated value of mu = 0.353 Value of mu given = 0.705 CHEMW_01 Alert A The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.90 <> 1.10 Calculated formula weight = 654.1136 Formula weight given = 1308.2000
Alert Level C:
CHEMW_01 Alert C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C23 H53 N1 O8 Zr2 Atom count from the _atom_site data: C46 H54 N2 O16 Zr4 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C23 H53 N O8 Zr2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 92.00 184.00 -92.00 H 212.00 216.00 -4.00 N 4.00 8.00 -4.00 O 32.00 64.00 -32.00 Zr 8.00 16.00 -8.00 Difference between formula and atom_site contents detected. ALERT: Large difference may be due to a symmetry error - see SYMMG tests CHEMW_03 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_weight 1308.20 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 46.00 552.51 H 1.01 54.00 54.43 N 14.01 2.00 28.01 O 16.00 16.00 255.98 Zr 91.22 4.00 364.90 Calculated formula weight 1255.83 The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.99 <> 1.01
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996) and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX (Farrugia, 1997, 1999); software used to prepare material for publication: SHELXL97.
[Zr4(C5H11NO2)2(C3H7O)12] | Dx = 1.388 Mg m−3 |
Mr = 1308.2 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 8192 reflections |
a = 18.271 (6) Å | θ = 2.5–24.8° |
b = 16.941 (5) Å | µ = 0.71 mm−1 |
c = 20.221 (6) Å | T = 170 K |
V = 6259 (3) Å3 | Block, colourless |
Z = 4 | 0.70 × 0.40 × 0.20 mm |
F(000) = 2736 |
Siemens SMART CCD area-detector diffractometer | 6435 independent reflections |
Radiation source: fine-focus sealed tube | 4298 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.5°, θmin = 2.2° |
φ and ω scans | h = −22→22 |
Absorption correction: multi-scan (Blessing, 1995) | k = −21→18 |
Tmin = 0.555, Tmax = 0.868 | l = −25→25 |
75801 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0932P)2 + 16.9738P] where P = (Fo2 + 2Fc2)/3 |
6435 reflections | (Δ/σ)max = 0.001 |
306 parameters | Δρmax = 1.14 e Å−3 |
2 restraints | Δρmin = −1.05 e Å−3 |
Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 0.8 mm diameter collimator was used. |
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. Conformational disorder in the methyliminodiethanolate (MDEA), bridging n-propanolate (O4) and in terminal n-propanolate ligands except those at O6 were modelled by two conformations (a/b) and a common isotropic thermal parameter. Specifically in the MDEA, C72a/C72b had final occupancies of 0.701 (13)/0.299 (13) and U of 0.054 (2) Å2; C21a,C22a,C23a/C21b,C22b,C23b 0.585 (11)/0.415 (11) and U of 0.099 (2) Å2; C31a,C32a,c33a/C31b,C32b,C33b 0.540 (11)/0.460 (11) and U of 0.103 (3) Å2 C41a,C43a/C42b,C43b 0.54 (2)/0.46 (2) and U of 0.076 (2) Å2. There was further disorder in the O6 n-propanolate which could only be modelled by constraining the sum occupancy of atoms C62a, C63a, C62b, C63b, C63c to be two carbon atoms (SHELXL SUMP function) with final common U of 0.103 (3) Å2; atoms 62a & 63a had the same occupancy at 0.390 (13); C63b is a common site for at least two of the conformations refining to an occupancy of 0.660 (14). The bondlength C41—C42a and C41—C42b were constrained to be the same length (SADI with e.s.d. 0.03). 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 | Occ. (<1) | |
Zr1 | 0.22290 (3) | 0.62102 (3) | 0.45075 (3) | 0.04461 (18) | |
Zr2 | 0.07741 (3) | 0.51066 (3) | 0.44276 (2) | 0.03602 (16) | |
O1 | 0.3132 (2) | 0.5694 (3) | 0.4774 (3) | 0.0731 (14) | |
O2 | 0.2592 (2) | 0.6754 (3) | 0.3716 (2) | 0.0595 (11) | |
O3 | 0.2162 (3) | 0.7104 (3) | 0.5124 (2) | 0.0672 (13) | |
O4 | 0.15329 (19) | 0.5458 (2) | 0.51802 (18) | 0.0437 (8) | |
O5 | 0.10460 (19) | 0.6317 (2) | 0.42051 (19) | 0.0427 (8) | |
O6 | 0.0300 (2) | 0.4872 (3) | 0.3598 (2) | 0.0590 (11) | |
O7 | 0.1850 (2) | 0.5178 (2) | 0.3941 (2) | 0.0503 (10) | |
O8 | 0.02044 (19) | 0.4349 (2) | 0.51333 (18) | 0.0424 (8) | |
N1 | 0.1353 (3) | 0.3828 (3) | 0.4456 (3) | 0.0628 (15) | |
C11 | 0.3819 (5) | 0.5387 (7) | 0.4935 (7) | 0.136 (5) | |
H11A | 0.4041 | 0.5142 | 0.4539 | 0.163* | |
H11B | 0.3765 | 0.4975 | 0.5279 | 0.163* | |
C12 | 0.4349 (5) | 0.6094 (8) | 0.5208 (7) | 0.137 (5) | |
H12A | 0.4832 | 0.5871 | 0.5327 | 0.164* | |
H12B | 0.4424 | 0.6488 | 0.4853 | 0.164* | |
C13 | 0.4027 (8) | 0.6482 (9) | 0.5789 (8) | 0.159 (5)* | |
H13A | 0.3532 | 0.6664 | 0.5682 | 0.191* | |
H13B | 0.4330 | 0.6936 | 0.5915 | 0.191* | |
H13C | 0.4005 | 0.6107 | 0.6157 | 0.191* | |
C41 | 0.1458 (3) | 0.5526 (4) | 0.5871 (3) | 0.0589 (16) | |
H41A | 0.1064 | 0.5176 | 0.6036 | 0.071* | |
H41B | 0.1344 | 0.6077 | 0.5999 | 0.071* | |
C51 | 0.0886 (3) | 0.6703 (4) | 0.3589 (3) | 0.0556 (15) | |
H51A | 0.0382 | 0.6567 | 0.3450 | 0.067* | |
H51B | 0.1227 | 0.6509 | 0.3245 | 0.067* | |
C52 | 0.0953 (4) | 0.7578 (4) | 0.3642 (4) | 0.074 (2) | |
H52A | 0.1453 | 0.7718 | 0.3787 | 0.089* | |
H52B | 0.0603 | 0.7778 | 0.3976 | 0.089* | |
C53 | 0.0792 (6) | 0.7968 (6) | 0.2962 (5) | 0.124 (4) | |
H53A | 0.0842 | 0.8542 | 0.3001 | 0.186* | |
H53B | 0.0292 | 0.7838 | 0.2824 | 0.186* | |
H53C | 0.1140 | 0.7770 | 0.2633 | 0.186* | |
C61 | 0.0054 (8) | 0.4677 (8) | 0.2969 (5) | 0.143 (5) | |
C71 | 0.2267 (4) | 0.4495 (4) | 0.3801 (4) | 0.076 (2) | |
H71A | 0.2790 | 0.4637 | 0.3759 | 0.091* | |
H71B | 0.2104 | 0.4262 | 0.3377 | 0.091* | |
C21A | 0.2733 (10) | 0.6898 (11) | 0.3040 (10) | 0.099 (2)* | 0.596 (11) |
C22A | 0.3471 (10) | 0.6611 (10) | 0.2866 (9) | 0.099 (2)* | 0.596 (11) |
C23A | 0.3602 (10) | 0.6742 (11) | 0.2098 (9) | 0.099 (2)* | 0.596 (11) |
C31A | 0.1610 (13) | 0.7661 (12) | 0.5369 (11) | 0.103 (3)* | 0.538 (12) |
C32A | 0.1792 (11) | 0.7859 (12) | 0.6047 (11) | 0.103 (3)* | 0.538 (12) |
C33A | 0.1246 (12) | 0.8457 (12) | 0.6358 (10) | 0.103 (3)* | 0.538 (12) |
C42A | 0.2246 (8) | 0.5258 (12) | 0.6162 (9) | 0.077 (2)* | 0.547 (20) |
C43A | 0.2230 (10) | 0.5369 (12) | 0.6918 (8) | 0.077 (2)* | 0.547 (20) |
C62A | −0.0183 (16) | 0.5324 (16) | 0.2500 (15) | 0.103 (3)* | 0.374 (13) |
C63A | −0.031 (2) | 0.5132 (17) | 0.1750 (15) | 0.103 (3)* | 0.374 (13) |
C72A | 0.2171 (5) | 0.3918 (6) | 0.4338 (5) | 0.055 (2)* | 0.701 (13) |
H72A | 0.2416 | 0.4107 | 0.4745 | 0.066* | 0.701 (13) |
H72B | 0.2388 | 0.3404 | 0.4212 | 0.066* | 0.701 (13) |
C73 | 0.0989 (6) | 0.3271 (5) | 0.4010 (5) | 0.105 (3) | |
H73A | 0.1181 | 0.2738 | 0.4087 | 0.126* | |
H73B | 0.1082 | 0.3425 | 0.3551 | 0.126* | |
H73C | 0.0461 | 0.3277 | 0.4095 | 0.126* | |
C74 | 0.1269 (4) | 0.3530 (4) | 0.5127 (4) | 0.076 (2) | |
H74A | 0.1580 | 0.3840 | 0.5433 | 0.092* | |
H74B | 0.1427 | 0.2972 | 0.5147 | 0.092* | |
C81 | 0.0474 (4) | 0.3598 (4) | 0.5332 (4) | 0.0672 (19) | |
H81A | 0.0184 | 0.3175 | 0.5119 | 0.081* | |
H82B | 0.0430 | 0.3540 | 0.5817 | 0.081* | |
C21B | 0.3011 (16) | 0.6567 (16) | 0.3159 (14) | 0.099 (2)* | 0.404 (11) |
C22B | 0.2876 (13) | 0.7218 (15) | 0.2626 (14) | 0.099 (2)* | 0.404 (11) |
C23B | 0.3481 (15) | 0.7236 (17) | 0.2049 (13) | 0.099 (2)* | 0.404 (11) |
C31B | 0.1973 (15) | 0.7565 (15) | 0.5688 (14) | 0.103 (3)* | 0.462 (12) |
C32B | 0.1141 (15) | 0.7752 (14) | 0.5568 (12) | 0.103 (3)* | 0.462 (12) |
C33B | 0.0852 (14) | 0.8211 (14) | 0.6201 (12) | 0.103 (3)* | 0.462 (12) |
C42B | 0.2163 (10) | 0.5566 (14) | 0.6246 (10) | 0.077 (2)* | 0.453 (20) |
C43B | 0.2016 (12) | 0.5721 (14) | 0.6982 (10) | 0.077 (2)* | 0.453 (20) |
C62B | 0.0419 (10) | 0.4968 (9) | 0.2456 (9) | 0.103 (3)* | 0.658 (14) |
C63B | 0.012 (4) | 0.501 (3) | 0.177 (3) | 0.103 (3)* | 0.202 (22) |
C63C | 0.1066 (16) | 0.4898 (15) | 0.2367 (14) | 0.103 (3)* | 0.392 (17) |
C72B | 0.1955 (12) | 0.3817 (12) | 0.3963 (12) | 0.055 (2)* | 0.299 (13) |
H72C | 0.2342 | 0.3463 | 0.4133 | 0.066* | 0.299 (13) |
H72D | 0.1762 | 0.3576 | 0.3553 | 0.066* | 0.299 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zr1 | 0.0334 (3) | 0.0465 (3) | 0.0540 (4) | −0.0050 (2) | 0.0023 (2) | 0.0042 (2) |
Zr2 | 0.0311 (3) | 0.0354 (3) | 0.0415 (3) | −0.00093 (19) | 0.0041 (2) | −0.0025 (2) |
O1 | 0.035 (2) | 0.098 (4) | 0.087 (3) | 0.006 (2) | −0.002 (2) | 0.021 (3) |
O2 | 0.053 (2) | 0.067 (3) | 0.058 (3) | −0.014 (2) | 0.014 (2) | 0.003 (2) |
O3 | 0.071 (3) | 0.063 (3) | 0.068 (3) | −0.019 (2) | 0.014 (2) | −0.013 (2) |
O4 | 0.040 (2) | 0.049 (2) | 0.042 (2) | −0.0041 (17) | 0.0013 (16) | 0.0055 (17) |
O5 | 0.0370 (19) | 0.045 (2) | 0.046 (2) | 0.0017 (16) | 0.0017 (16) | 0.0048 (16) |
O6 | 0.046 (2) | 0.079 (3) | 0.052 (2) | −0.009 (2) | −0.0001 (19) | −0.016 (2) |
O7 | 0.045 (2) | 0.045 (2) | 0.061 (3) | −0.0006 (17) | 0.0145 (19) | −0.0053 (18) |
O8 | 0.0393 (19) | 0.0360 (18) | 0.052 (2) | 0.0024 (15) | 0.0088 (17) | 0.0028 (16) |
N1 | 0.058 (3) | 0.041 (3) | 0.089 (4) | 0.002 (2) | 0.029 (3) | −0.006 (3) |
C11 | 0.064 (6) | 0.133 (9) | 0.210 (14) | 0.025 (6) | −0.007 (7) | 0.068 (9) |
C12 | 0.064 (6) | 0.177 (12) | 0.169 (12) | 0.017 (7) | −0.036 (7) | 0.028 (10) |
C41 | 0.054 (4) | 0.086 (5) | 0.037 (3) | −0.020 (3) | −0.007 (3) | 0.005 (3) |
C51 | 0.045 (3) | 0.063 (4) | 0.059 (4) | 0.002 (3) | 0.000 (3) | 0.016 (3) |
C52 | 0.064 (4) | 0.065 (4) | 0.093 (6) | 0.014 (3) | 0.014 (4) | 0.032 (4) |
C53 | 0.134 (9) | 0.105 (7) | 0.133 (9) | 0.026 (6) | 0.013 (7) | 0.081 (7) |
C61 | 0.193 (13) | 0.179 (11) | 0.057 (6) | −0.038 (10) | −0.035 (7) | −0.022 (7) |
C71 | 0.056 (4) | 0.064 (4) | 0.109 (6) | 0.006 (3) | 0.035 (4) | −0.013 (4) |
C73 | 0.148 (9) | 0.062 (5) | 0.106 (7) | −0.002 (5) | 0.029 (7) | −0.017 (5) |
C74 | 0.068 (5) | 0.057 (4) | 0.105 (6) | 0.016 (3) | 0.021 (4) | 0.015 (4) |
C81 | 0.064 (4) | 0.048 (3) | 0.090 (5) | 0.014 (3) | 0.024 (4) | 0.018 (3) |
Zr1—O1 | 1.944 (4) | C51—C52 | 1.490 (10) |
Zr1—O2 | 1.962 (4) | C51—H51A | 0.9900 |
Zr1—O3 | 1.965 (5) | C51—H51B | 0.9900 |
Zr1—O7 | 2.202 (4) | C52—C53 | 1.552 (11) |
Zr1—O5 | 2.253 (4) | C52—H52A | 0.9900 |
Zr1—O4 | 2.256 (4) | C52—H52B | 0.9900 |
Zr2—O6 | 1.929 (4) | C53—H53A | 0.9800 |
Zr2—O4 | 2.143 (4) | C53—H53B | 0.9800 |
Zr2—O5 | 2.158 (4) | C53—H53C | 0.9800 |
Zr2—O8 | 2.183 (3) | C61—C62B | 1.33 (2) |
Zr2—O8i | 2.199 (3) | C61—C62A | 1.51 (3) |
Zr2—O7 | 2.202 (4) | C71—C72B | 1.32 (2) |
Zr2—N1 | 2.412 (5) | C71—C72A | 1.472 (12) |
O1—C11 | 1.396 (9) | C71—H71A | 0.9900 |
O2—C21B | 1.40 (3) | C71—H71B | 0.9900 |
O2—C21A | 1.41 (2) | C21A—C22A | 1.48 (3) |
O3—C31B | 1.42 (3) | C22A—C23A | 1.59 (2) |
O3—C31A | 1.47 (2) | C31A—C32A | 1.45 (3) |
O4—C41 | 1.409 (7) | C32A—C33A | 1.56 (3) |
O5—C51 | 1.437 (7) | C42A—C43A | 1.54 (2) |
O6—C61 | 1.389 (10) | C62A—C63A | 1.57 (4) |
O7—C71 | 1.413 (7) | C72A—H72A | 0.9900 |
O8—C81 | 1.422 (7) | C72A—H72B | 0.9900 |
O8—Zr2i | 2.199 (3) | C73—H73A | 0.9800 |
N1—C74 | 1.455 (10) | C73—H73B | 0.9800 |
N1—C73 | 1.465 (11) | C73—H73C | 0.9800 |
N1—C72B | 1.48 (2) | C74—C81 | 1.515 (10) |
N1—C72A | 1.521 (11) | C74—H74A | 0.9900 |
C11—C12 | 1.635 (17) | C74—H74B | 0.9900 |
C11—H11A | 0.9900 | C81—H81A | 0.9900 |
C11—H11B | 0.9900 | C81—H82B | 0.9900 |
C12—C13 | 1.469 (17) | C21B—C22B | 1.56 (4) |
C12—H12A | 0.9900 | C22B—C23B | 1.61 (4) |
C12—H12B | 0.9900 | C31B—C32B | 1.57 (4) |
C13—H13A | 0.9800 | C32B—C33B | 1.59 (3) |
C13—H13B | 0.9800 | C42B—C43B | 1.53 (3) |
C13—H13C | 0.9800 | C62B—C63C | 1.20 (3) |
C41—C42B | 1.496 (17) | C62B—C63B | 1.49 (6) |
C41—C42A | 1.621 (15) | C72B—H72C | 0.9900 |
C41—H41A | 0.9900 | C72B—H72D | 0.9900 |
C41—H41B | 0.9900 | ||
O1—Zr1—O2 | 98.7 (2) | H13B—C13—H13C | 109.5 |
O1—Zr1—O3 | 102.9 (2) | O4—C41—C42B | 115.0 (10) |
O2—Zr1—O3 | 100.18 (19) | O4—C41—C42A | 104.5 (8) |
O1—Zr1—O7 | 93.1 (2) | C42B—C41—C42A | 20.6 (9) |
O2—Zr1—O7 | 93.15 (17) | O4—C41—H41A | 110.9 |
O3—Zr1—O7 | 157.25 (16) | C42B—C41—H41A | 118.8 |
O1—Zr1—O5 | 157.78 (18) | C42A—C41—H41A | 110.9 |
O2—Zr1—O5 | 93.72 (16) | O4—C41—H41B | 110.9 |
O3—Zr1—O5 | 92.87 (17) | C42B—C41—H41B | 90.3 |
O7—Zr1—O5 | 67.75 (14) | C42A—C41—H41B | 110.9 |
O1—Zr1—O4 | 93.29 (17) | H41A—C41—H41B | 108.9 |
O2—Zr1—O4 | 161.33 (16) | O5—C51—C52 | 112.0 (6) |
O3—Zr1—O4 | 91.00 (17) | O5—C51—H51A | 109.2 |
O7—Zr1—O4 | 71.82 (14) | C52—C51—H51A | 109.2 |
O5—Zr1—O4 | 70.64 (13) | O5—C51—H51B | 109.2 |
O6—Zr2—O4 | 164.83 (16) | C52—C51—H51B | 109.2 |
O6—Zr2—O5 | 96.78 (17) | H51A—C51—H51B | 107.9 |
O4—Zr2—O5 | 74.63 (14) | C51—C52—C53 | 110.1 (7) |
O6—Zr2—O8 | 103.47 (16) | C51—C52—H52A | 109.6 |
O4—Zr2—O8 | 90.44 (14) | C53—C52—H52A | 109.6 |
O5—Zr2—O8 | 143.59 (14) | C51—C52—H52B | 109.6 |
O6—Zr2—O8i | 94.16 (16) | C53—C52—H52B | 109.6 |
O4—Zr2—O8i | 97.05 (14) | H52A—C52—H52B | 108.1 |
O5—Zr2—O8i | 82.69 (13) | C52—C53—H53A | 109.5 |
O8—Zr2—O8i | 66.11 (15) | C52—C53—H53B | 109.5 |
O6—Zr2—O7 | 91.37 (17) | H53A—C53—H53B | 109.5 |
O4—Zr2—O7 | 73.99 (15) | C52—C53—H53C | 109.5 |
O5—Zr2—O7 | 69.45 (14) | H53A—C53—H53C | 109.5 |
O8—Zr2—O7 | 138.59 (14) | H53B—C53—H53C | 109.5 |
O8i—Zr2—O7 | 152.05 (13) | C62B—C61—O6 | 117.7 (13) |
O6—Zr2—N1 | 91.9 (2) | C62B—C61—C62A | 52.0 (13) |
O4—Zr2—N1 | 87.07 (18) | O6—C61—C62A | 119.6 (15) |
O5—Zr2—N1 | 139.28 (16) | C72B—C71—O7 | 115.4 (10) |
O8—Zr2—N1 | 70.45 (15) | C72B—C71—C72A | 35.8 (10) |
O8i—Zr2—N1 | 136.36 (15) | O7—C71—C72A | 109.4 (6) |
O7—Zr2—N1 | 70.64 (16) | C72B—C71—H71A | 130.4 |
C11—O1—Zr1 | 174.2 (6) | O7—C71—H71A | 109.8 |
C21B—O2—C21A | 32.8 (11) | C72A—C71—H71A | 109.8 |
C21B—O2—Zr1 | 137.4 (12) | C72B—C71—H71B | 74.9 |
C21A—O2—Zr1 | 158.8 (8) | O7—C71—H71B | 109.8 |
C31B—O3—C31A | 37.8 (11) | C72A—C71—H71B | 109.8 |
C31B—O3—Zr1 | 161.0 (10) | H71A—C71—H71B | 108.3 |
C31A—O3—Zr1 | 138.8 (9) | O2—C21A—C22A | 109.9 (15) |
C41—O4—Zr2 | 131.6 (3) | C21A—C22A—C23A | 108.9 (15) |
C41—O4—Zr1 | 127.4 (3) | C32A—C31A—O3 | 108.1 (19) |
Zr2—O4—Zr1 | 95.36 (14) | C31A—C32A—C33A | 112.7 (19) |
C51—O5—Zr2 | 124.5 (3) | C43A—C42A—C41 | 108.0 (11) |
C51—O5—Zr1 | 117.8 (3) | C61—C62A—C63A | 120 (2) |
Zr2—O5—Zr1 | 95.03 (14) | C71—C72A—N1 | 107.4 (7) |
C61—O6—Zr2 | 172.1 (7) | C71—C72A—H72A | 110.2 |
C71—O7—Zr2 | 121.7 (4) | N1—C72A—H72A | 110.2 |
C71—O7—Zr1 | 125.8 (4) | C71—C72A—H72B | 110.2 |
Zr2—O7—Zr1 | 95.28 (15) | N1—C72A—H72B | 110.2 |
C81—O8—Zr2 | 123.0 (3) | H72A—C72A—H72B | 108.5 |
C81—O8—Zr2i | 122.9 (3) | N1—C73—H73A | 109.5 |
Zr2—O8—Zr2i | 113.89 (15) | N1—C73—H73B | 109.5 |
C74—N1—C73 | 107.6 (6) | N1—C73—H73C | 109.5 |
C74—N1—C72B | 134.4 (11) | N1—C74—C81 | 109.2 (6) |
C73—N1—C72B | 85.1 (11) | N1—C74—H74A | 109.8 |
C74—N1—C72A | 106.5 (6) | C81—C74—H74A | 109.8 |
C73—N1—C72A | 114.5 (7) | N1—C74—H74B | 109.8 |
C72B—N1—C72A | 33.7 (9) | C81—C74—H74B | 109.8 |
C74—N1—Zr2 | 106.7 (4) | H74A—C74—H74B | 108.3 |
C73—N1—Zr2 | 111.4 (5) | O8—C81—C74 | 108.8 (5) |
C72B—N1—Zr2 | 108.6 (8) | O8—C81—H81A | 109.9 |
C72A—N1—Zr2 | 109.7 (4) | C74—C81—H81A | 109.9 |
O1—C11—C12 | 109.8 (9) | O8—C81—H82B | 109.9 |
O1—C11—H11A | 109.7 | C74—C81—H82B | 109.9 |
C12—C11—H11A | 109.7 | H81A—C81—H82B | 108.3 |
O1—C11—H11B | 109.7 | O2—C21B—C22B | 108 (2) |
C12—C11—H11B | 109.7 | C21B—C22B—C23B | 114 (2) |
H11A—C11—H11B | 108.2 | O3—C31B—C32B | 103 (2) |
C13—C12—C11 | 111.2 (11) | C31B—C32B—C33B | 107 (2) |
C13—C12—H12A | 109.4 | C41—C42B—C43B | 110.4 (14) |
C11—C12—H12A | 109.4 | C63C—C62B—C61 | 125 (2) |
C13—C12—H12B | 109.4 | C63C—C62B—C63B | 103 (3) |
C11—C12—H12B | 109.4 | C61—C62B—C63B | 124 (3) |
H12A—C12—H12B | 108.0 | C71—C72B—N1 | 118.4 (16) |
C12—C13—H13A | 109.5 | C71—C72B—H72C | 107.7 |
C12—C13—H13B | 109.5 | N1—C72B—H72C | 107.7 |
H13A—C13—H13B | 109.5 | C71—C72B—H72D | 107.7 |
C12—C13—H13C | 109.5 | N1—C72B—H72D | 107.7 |
H13A—C13—H13C | 109.5 | H72C—C72B—H72D | 107.1 |
O1—Zr1—O2—C21B | 47.3 (17) | O4—Zr1—O7—Zr2 | 35.00 (13) |
O3—Zr1—O2—C21B | 152.2 (17) | O6—Zr2—O8—C81 | 96.3 (5) |
O7—Zr1—O2—C21B | −46.3 (17) | O4—Zr2—O8—C81 | −77.6 (5) |
O5—Zr1—O2—C21B | −114.2 (17) | O5—Zr2—O8—C81 | −141.8 (5) |
O4—Zr1—O2—C21B | −81.9 (18) | O8i—Zr2—O8—C81 | −175.1 (6) |
O1—Zr1—O3—C31A | −162.1 (14) | O7—Zr2—O8—C81 | −11.7 (6) |
O2—Zr1—O3—C31A | 96.5 (14) | N1—Zr2—O8—C81 | 9.1 (5) |
O7—Zr1—O3—C31A | −28.4 (15) | O6—Zr2—O8—Zr2i | −88.6 (2) |
O5—Zr1—O3—C31A | 2.2 (14) | O4—Zr2—O8—Zr2i | 97.52 (18) |
O4—Zr1—O3—C31A | −68.5 (14) | O5—Zr2—O8—Zr2i | 33.4 (3) |
O6—Zr2—O4—C41 | 174.0 (7) | O7—Zr2—O8—Zr2i | 163.43 (17) |
O5—Zr2—O4—C41 | 117.0 (5) | N1—Zr2—O8—Zr2i | −175.8 (2) |
O8—Zr2—O4—C41 | −29.3 (5) | O6—Zr2—N1—C74 | −135.5 (5) |
O8i—Zr2—O4—C41 | 36.7 (5) | O4—Zr2—N1—C74 | 59.7 (5) |
O7—Zr2—O4—C41 | −170.4 (5) | O5—Zr2—N1—C74 | 121.9 (4) |
N1—Zr2—O4—C41 | −99.7 (5) | O8—Zr2—N1—C74 | −31.8 (4) |
O6—Zr2—O4—Zr1 | 20.0 (7) | O8i—Zr2—N1—C74 | −37.5 (6) |
O5—Zr2—O4—Zr1 | −36.93 (13) | O7—Zr2—N1—C74 | 133.7 (5) |
O8—Zr2—O4—Zr1 | 176.71 (14) | O6—Zr2—N1—C73 | −18.3 (5) |
O8i—Zr2—O4—Zr1 | −117.31 (14) | O4—Zr2—N1—C73 | 176.9 (5) |
O7—Zr2—O4—Zr1 | 35.62 (13) | O5—Zr2—N1—C73 | −120.9 (5) |
N1—Zr2—O4—Zr1 | 106.32 (17) | O8—Zr2—N1—C73 | 85.4 (5) |
O1—Zr1—O4—C41 | 76.1 (5) | O8i—Zr2—N1—C73 | 79.7 (6) |
O2—Zr1—O4—C41 | −154.0 (6) | O7—Zr2—N1—C73 | −109.1 (5) |
O3—Zr1—O4—C41 | −26.9 (5) | O6—Zr2—N1—C72B | 73.8 (11) |
O7—Zr1—O4—C41 | 168.3 (5) | O4—Zr2—N1—C72B | −91.1 (11) |
O5—Zr1—O4—C41 | −119.6 (5) | O5—Zr2—N1—C72B | −28.8 (12) |
O1—Zr1—O4—Zr2 | −128.3 (2) | O8—Zr2—N1—C72B | 177.4 (11) |
O2—Zr1—O4—Zr2 | 1.6 (6) | O8i—Zr2—N1—C72B | 171.8 (11) |
O3—Zr1—O4—Zr2 | 128.71 (19) | O7—Zr2—N1—C72B | −17.0 (11) |
O7—Zr1—O4—Zr2 | −36.11 (14) | O6—Zr2—N1—C72A | 109.5 (6) |
O5—Zr1—O4—Zr2 | 36.01 (13) | O4—Zr2—N1—C72A | −55.3 (5) |
O6—Zr2—O5—C51 | −1.3 (4) | O5—Zr2—N1—C72A | 6.9 (7) |
O4—Zr2—O5—C51 | 166.0 (4) | O8—Zr2—N1—C72A | −146.8 (6) |
O8—Zr2—O5—C51 | −125.1 (4) | O8i—Zr2—N1—C72A | −152.5 (5) |
O8i—Zr2—O5—C51 | −94.6 (4) | O7—Zr2—N1—C72A | 18.7 (5) |
O7—Zr2—O5—C51 | 87.6 (4) | O1—C11—C12—C13 | 58.2 (14) |
N1—Zr2—O5—C51 | 99.6 (5) | Zr2—O4—C41—C42B | 163.2 (11) |
O6—Zr2—O5—Zr1 | −130.29 (16) | Zr1—O4—C41—C42B | −50.1 (12) |
O4—Zr2—O5—Zr1 | 36.96 (13) | Zr2—O4—C41—C42A | 144.4 (8) |
O8—Zr2—O5—Zr1 | 105.9 (2) | Zr1—O4—C41—C42A | −69.0 (9) |
O8i—Zr2—O5—Zr1 | 136.37 (16) | Zr2—O5—C51—C52 | 164.7 (4) |
O7—Zr2—O5—Zr1 | −41.37 (15) | Zr1—O5—C51—C52 | −76.4 (6) |
N1—Zr2—O5—Zr1 | −29.4 (3) | O5—C51—C52—C53 | 178.8 (6) |
O1—Zr1—O5—C51 | −123.7 (6) | Zr2—O7—C71—C72B | 2.0 (16) |
O2—Zr1—O5—C51 | 0.2 (4) | Zr1—O7—C71—C72B | 127.4 (14) |
O3—Zr1—O5—C51 | 100.6 (4) | Zr2—O7—C71—C72A | −36.3 (9) |
O7—Zr1—O5—C51 | −91.6 (4) | Zr1—O7—C71—C72A | 89.0 (7) |
O4—Zr1—O5—C51 | −169.3 (4) | O2—C21A—C22A—C23A | 177.3 (13) |
O1—Zr1—O5—Zr2 | 9.9 (5) | Zr1—O3—C31A—C32A | 147.9 (11) |
O2—Zr1—O5—Zr2 | 133.84 (17) | O3—C31A—C32A—C33A | 179.3 (15) |
O3—Zr1—O5—Zr2 | −125.75 (18) | O4—C41—C42A—C43A | 176.2 (10) |
O7—Zr1—O5—Zr2 | 41.96 (14) | C72B—C71—C72A—N1 | −56.7 (17) |
O4—Zr1—O5—Zr2 | −35.70 (13) | O7—C71—C72A—N1 | 50.1 (9) |
O6—Zr2—O7—C71 | −82.3 (5) | C74—N1—C72A—C71 | −157.5 (7) |
O4—Zr2—O7—C71 | 101.8 (5) | C73—N1—C72A—C71 | 83.6 (9) |
O5—Zr2—O7—C71 | −179.0 (6) | C72B—N1—C72A—C71 | 51.9 (16) |
O8—Zr2—O7—C71 | 30.0 (6) | Zr2—N1—C72A—C71 | −42.4 (8) |
O8i—Zr2—O7—C71 | 176.2 (5) | C73—N1—C74—C81 | −69.3 (8) |
N1—Zr2—O7—C71 | 9.2 (5) | C72B—N1—C74—C81 | −170.1 (13) |
O6—Zr2—O7—Zr1 | 139.31 (18) | C72A—N1—C74—C81 | 167.5 (6) |
O4—Zr2—O7—Zr1 | −36.64 (14) | Zr2—N1—C74—C81 | 50.4 (7) |
O5—Zr2—O7—Zr1 | 42.59 (14) | Zr2—O8—C81—C74 | 14.8 (8) |
O8—Zr2—O7—Zr1 | −108.4 (2) | Zr2i—O8—C81—C74 | −159.9 (5) |
O8i—Zr2—O7—Zr1 | 37.8 (4) | N1—C74—C81—O8 | −44.0 (8) |
N1—Zr2—O7—Zr1 | −129.2 (2) | C21A—O2—C21B—C22B | 13.5 (19) |
O1—Zr1—O7—C71 | −8.4 (5) | Zr1—O2—C21B—C22B | 162.3 (11) |
O2—Zr1—O7—C71 | 90.5 (5) | O2—C21B—C22B—C23B | 163.1 (19) |
O3—Zr1—O7—C71 | −143.5 (6) | C31A—O3—C31B—C32B | 18.6 (18) |
O5—Zr1—O7—C71 | −176.8 (5) | Zr1—O3—C31B—C32B | −73 (4) |
O4—Zr1—O7—C71 | −100.8 (5) | O3—C31B—C32B—C33B | 175.6 (16) |
O1—Zr1—O7—Zr2 | 127.45 (19) | O4—C41—C42B—C43B | 174.4 (11) |
O2—Zr1—O7—Zr2 | −133.70 (18) | C42A—C41—C42B—C43B | −123 (4) |
O3—Zr1—O7—Zr2 | −7.6 (5) | C74—N1—C72B—C71 | −112.9 (17) |
O5—Zr1—O7—Zr2 | −40.96 (14) |
Symmetry code: (i) −x, −y+1, −z+1. |