Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014751/om6048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014751/om6048Isup2.hkl |
CCDC reference: 175328
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.008 Å
- R factor = 0.054
- wR factor = 0.128
- Data-to-parameter ratio = 13.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.284 Value of mu given = 0.280 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 8481 Count of symmetry unique reflns 4410 Completeness (_total/calc) 192.31% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4071 Fraction of Friedel pairs measured 0.923 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound, (I), was synthesized by combining acenaphthylene (4.60 g, 75% pure by 1H NMR, 22.7 mmol) and activated calcium (2.1 g, 52 mmol); THF (150 ml) was condensed into the vessel. The clear yellow solution with calcium on the bottom turned into a brown turbid mixture after stirring overnight at room temperature. The product was extracted with hot THF until the extract became colorless. The raw product was washed twice with benzene (2 × 50 ml) and dried under reduced pressure. Isolation gave 5.05 g (10.33 mmol, 91%) of a green–yellow product. The 1H NMR spectrum showed one isomer (rac) was present. Crystals suitable for X-ray analysis were obtained by slow cooling of a hot saturated THF solution of the title compound. 1H NMR (500.13 MHz, THF-d8): δ 6.87 (d, 1JHH = 8.25 Hz, 2H, H-5), 6.60 (dd, 3JHH = 9.68 Hz, 4JHH = 1.93 Hz, 2H, H-6), 6.40 (dd, 3JHH = 8.25 Hz, 3JHH = 6.50 Hz, 2H, H-4), 6.33 (d, 3JHH = 3.14 Hz, 2H, H-2), 6.22 (d, 3JHH = 6.50 Hz, 2H, H-3), 5.99 (dd, 3JHH = 9.68 Hz, 3JHH = 3.53 Hz, 2H, H-7), 5.59 (d, 3JHH = 3.14 Hz, 2H, H-1), 4.54 (br, 2H, H-8); 3.58 (m, 8H, THF), 1.73 (m, 8H, THF). 13C NMR (125.77 MHz, THF-d8): δ 135.56 (d, 1JCH = 157.7 Hz), 128.61 (s), 127.24 (1JCH = 155.5 Hz), 124.22 (s), 120.70 (d, 1JCH = 154.3 Hz), 119.00 (d, 1JCH = 154.5 Hz), 113.52 (d, 1JCH = 159.0 Hz), 112.68 (d, 1JCH = 151.5 Hz), 112.14 (s), 96.18 (d, 1JCH = 163.0 Hz), 67.4 (m, THF), 50.00 (d, 1JCH = 130.7 Hz, C-8), 25.32 (m, THF).
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 1998); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: XCIF in SHELXTL.
[Ca(C24H12)(C4H8O)2] | Dx = 1.321 Mg m−3 |
Mr = 488.66 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 928 reflections |
a = 16.1497 (14) Å | θ = 2.3–22.5° |
b = 8.6805 (7) Å | µ = 0.28 mm−1 |
c = 35.047 (3) Å | T = 203 K |
V = 4913.2 (7) Å3 | Plate, yellow |
Z = 8 | 0.24 × 0.14 × 0.05 mm |
F(000) = 2080 |
Siemens SMART 1K diffractometer | 8481 independent reflections |
Radiation source: normal-focus sealed tube | 5906 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 8.3 pixels mm-1 | θmax = 25.0°, θmin = 1.2° |
ω scans | h = −16→19 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1999) | k = −10→10 |
Tmin = 0.935, Tmax = 0.986 | l = −39→41 |
36582 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0614P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
8481 reflections | Δρmax = 0.78 e Å−3 |
631 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.11 (5) |
[Ca(C24H12)(C4H8O)2] | V = 4913.2 (7) Å3 |
Mr = 488.66 | Z = 8 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 16.1497 (14) Å | µ = 0.28 mm−1 |
b = 8.6805 (7) Å | T = 203 K |
c = 35.047 (3) Å | 0.24 × 0.14 × 0.05 mm |
Siemens SMART 1K diffractometer | 8481 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1999) | 5906 reflections with I > 2σ(I) |
Tmin = 0.935, Tmax = 0.986 | Rint = 0.074 |
36582 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.128 | Δρmax = 0.78 e Å−3 |
S = 1.01 | Δρmin = −0.22 e Å−3 |
8481 reflections | Absolute structure: Flack (1983) |
631 parameters | Absolute structure parameter: 0.11 (5) |
1 restraint |
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 | ||
Ca1 | 0.51912 (5) | 0.87989 (10) | 0.71242 (3) | 0.0257 (2) | |
Ca2 | 0.74135 (6) | 0.62116 (10) | 0.95906 (3) | 0.0261 (2) | |
O1 | 0.4545 (2) | 1.0156 (4) | 0.66276 (14) | 0.0361 (11) | |
O2 | 0.4462 (2) | 1.0374 (4) | 0.75569 (11) | 0.0356 (9) | |
O3 | 0.8108 (2) | 0.4611 (4) | 0.91529 (11) | 0.0366 (9) | |
O4 | 0.8075 (2) | 0.4819 (4) | 1.00788 (13) | 0.0341 (10) | |
C1 | 0.4263 (3) | 0.6385 (5) | 0.73784 (14) | 0.0336 (12) | |
H1A | 0.3855 | 0.6428 | 0.7589 | 0.040* | |
C2 | 0.5101 (3) | 0.5901 (5) | 0.74127 (16) | 0.0327 (12) | |
H2A | 0.5366 | 0.5559 | 0.7653 | 0.039* | |
C3 | 0.5450 (3) | 0.5732 (5) | 0.70455 (14) | 0.0265 (11) | |
C4 | 0.4814 (3) | 0.6095 (5) | 0.67860 (13) | 0.0263 (11) | |
C5 | 0.4073 (3) | 0.6487 (5) | 0.69852 (14) | 0.0289 (12) | |
C6 | 0.3370 (3) | 0.6875 (6) | 0.67624 (16) | 0.0364 (12) | |
H6A | 0.2868 | 0.7139 | 0.6881 | 0.044* | |
C7 | 0.3431 (3) | 0.6861 (6) | 0.63736 (18) | 0.0454 (15) | |
H7A | 0.2957 | 0.7090 | 0.6229 | 0.055* | |
C8 | 0.4182 (3) | 0.6512 (6) | 0.61791 (15) | 0.0385 (13) | |
H8A | 0.4199 | 0.6538 | 0.5911 | 0.046* | |
C9 | 0.4881 (3) | 0.6138 (5) | 0.63823 (13) | 0.0291 (11) | |
C10 | 0.5699 (3) | 0.5784 (6) | 0.62399 (15) | 0.0356 (13) | |
H10A | 0.5791 | 0.5804 | 0.5975 | 0.043* | |
C11 | 0.6329 (3) | 0.5428 (6) | 0.64711 (17) | 0.0367 (13) | |
H11A | 0.6844 | 0.5244 | 0.6355 | 0.044* | |
C12 | 0.6297 (3) | 0.5294 (6) | 0.68978 (18) | 0.0312 (13) | |
H12A | 0.6396 | 0.4202 | 0.6965 | 0.037* | |
C13 | 0.7014 (2) | 0.6292 (5) | 0.70832 (16) | 0.0304 (10) | |
H13A | 0.7525 | 0.6118 | 0.6933 | 0.037* | |
C14 | 0.7175 (3) | 0.5758 (6) | 0.74873 (15) | 0.0351 (12) | |
H14A | 0.7336 | 0.4725 | 0.7519 | 0.042* | |
C15 | 0.7110 (3) | 0.6607 (6) | 0.78015 (15) | 0.0391 (14) | |
H15A | 0.7211 | 0.6150 | 0.8040 | 0.047* | |
C16 | 0.6886 (3) | 0.8229 (6) | 0.77835 (16) | 0.0384 (13) | |
C17 | 0.6817 (3) | 0.9251 (8) | 0.80853 (18) | 0.0534 (19) | |
H17A | 0.6892 | 0.8898 | 0.8336 | 0.064* | |
C18 | 0.6636 (4) | 1.0822 (8) | 0.8019 (2) | 0.057 (2) | |
H18A | 0.6591 | 1.1486 | 0.8230 | 0.068* | |
C19 | 0.6523 (3) | 1.1424 (7) | 0.7659 (2) | 0.0478 (17) | |
H19A | 0.6407 | 1.2475 | 0.7623 | 0.057* | |
C20 | 0.6588 (3) | 1.0396 (7) | 0.73423 (16) | 0.0346 (14) | |
C21 | 0.6768 (3) | 0.8831 (6) | 0.74184 (16) | 0.0317 (12) | |
C22 | 0.6828 (2) | 0.7996 (5) | 0.70767 (15) | 0.0271 (10) | |
C23 | 0.6665 (3) | 0.9076 (6) | 0.67852 (16) | 0.0311 (12) | |
H23A | 0.6763 | 0.8878 | 0.6511 | 0.037* | |
C24 | 0.6521 (3) | 1.0550 (7) | 0.69406 (17) | 0.0377 (15) | |
H24A | 0.6509 | 1.1532 | 0.6797 | 0.045* | |
C25 | 0.4869 (3) | 1.0557 (7) | 0.62539 (14) | 0.0409 (13) | |
H25A | 0.4653 | 0.9857 | 0.6058 | 0.049* | |
H25B | 0.5475 | 1.0507 | 0.6252 | 0.049* | |
C26 | 0.4575 (3) | 1.2185 (6) | 0.61837 (16) | 0.0453 (14) | |
H26A | 0.4421 | 1.2330 | 0.5916 | 0.054* | |
H26B | 0.5008 | 1.2931 | 0.6250 | 0.054* | |
C27 | 0.3819 (3) | 1.2373 (6) | 0.64451 (16) | 0.0440 (14) | |
H27A | 0.3918 | 1.3167 | 0.6639 | 0.053* | |
H27B | 0.3326 | 1.2652 | 0.6298 | 0.053* | |
C28 | 0.3718 (3) | 1.0802 (5) | 0.66276 (16) | 0.0351 (12) | |
H28A | 0.3505 | 1.0896 | 0.6888 | 0.042* | |
H28B | 0.3339 | 1.0158 | 0.6479 | 0.042* | |
C29 | 0.4316 (3) | 1.2035 (5) | 0.75306 (14) | 0.0394 (13) | |
H29A | 0.3766 | 1.2249 | 0.7426 | 0.047* | |
H29B | 0.4733 | 1.2527 | 0.7368 | 0.047* | |
C30 | 0.4382 (4) | 1.2609 (6) | 0.79376 (14) | 0.0438 (14) | |
H30A | 0.4945 | 1.2972 | 0.7992 | 0.053* | |
H30B | 0.3993 | 1.3456 | 0.7983 | 0.053* | |
C31 | 0.4170 (4) | 1.1237 (6) | 0.81850 (16) | 0.0520 (16) | |
H31A | 0.3641 | 1.1393 | 0.8316 | 0.062* | |
H31B | 0.4603 | 1.1052 | 0.8376 | 0.062* | |
C32 | 0.4115 (5) | 0.9899 (6) | 0.7903 (2) | 0.059 (2) | |
H32A | 0.4417 | 0.9005 | 0.8002 | 0.070* | |
H32B | 0.3536 | 0.9602 | 0.7865 | 0.070* | |
C33 | 0.6091 (3) | 0.4527 (7) | 0.97951 (16) | 0.0369 (14) | |
H33A | 0.6116 | 0.3563 | 0.9945 | 0.044* | |
C34 | 0.5944 (3) | 0.5996 (6) | 0.99498 (16) | 0.0311 (12) | |
H34A | 0.5854 | 0.6212 | 1.0224 | 0.037* | |
C35 | 0.5781 (2) | 0.7049 (5) | 0.96506 (14) | 0.0258 (11) | |
C36 | 0.5818 (3) | 0.6192 (6) | 0.93077 (15) | 0.0305 (12) | |
C37 | 0.6005 (3) | 0.4598 (7) | 0.93902 (18) | 0.0368 (14) | |
C38 | 0.6042 (3) | 0.3610 (7) | 0.9071 (2) | 0.0489 (16) | |
H38A | 0.6163 | 0.2560 | 0.9105 | 0.059* | |
C39 | 0.5903 (4) | 0.4176 (8) | 0.8714 (2) | 0.056 (2) | |
H39A | 0.5921 | 0.3487 | 0.8507 | 0.067* | |
C40 | 0.5736 (3) | 0.5730 (8) | 0.86388 (19) | 0.0477 (18) | |
H40A | 0.5661 | 0.6065 | 0.8386 | 0.057* | |
C41 | 0.5681 (3) | 0.6761 (7) | 0.89330 (16) | 0.0367 (14) | |
C42 | 0.5457 (3) | 0.8392 (6) | 0.89178 (15) | 0.0367 (13) | |
H42A | 0.5346 | 0.8847 | 0.8680 | 0.044* | |
C43 | 0.5405 (3) | 0.9257 (6) | 0.92341 (16) | 0.0370 (13) | |
H43A | 0.5227 | 1.0280 | 0.9202 | 0.044* | |
C44 | 0.5603 (3) | 0.8757 (5) | 0.96372 (14) | 0.0303 (11) | |
H44A | 0.5105 | 0.8947 | 0.9795 | 0.036* | |
C45 | 0.6317 (3) | 0.9770 (6) | 0.98009 (19) | 0.0342 (14) | |
H45A | 0.6218 | 1.0842 | 0.9716 | 0.041* | |
C46 | 0.6308 (3) | 0.9764 (6) | 1.02358 (18) | 0.0382 (14) | |
H46A | 0.5809 | 1.0043 | 1.0355 | 0.046* | |
C47 | 0.6943 (3) | 0.9398 (6) | 1.04645 (16) | 0.0389 (13) | |
H47A | 0.6863 | 0.9421 | 1.0730 | 0.047* | |
C48 | 0.7759 (3) | 0.8963 (5) | 1.03141 (14) | 0.0319 (11) | |
C49 | 0.8458 (3) | 0.8600 (5) | 1.05177 (15) | 0.0380 (13) | |
H49A | 0.8447 | 0.8625 | 1.0786 | 0.046* | |
C50 | 0.9197 (3) | 0.8186 (6) | 1.03237 (16) | 0.0376 (13) | |
H50A | 0.9668 | 0.7935 | 1.0468 | 0.045* | |
C51 | 0.9250 (3) | 0.8138 (6) | 0.99377 (17) | 0.0383 (13) | |
H51A | 0.9749 | 0.7856 | 0.9819 | 0.046* | |
C52 | 0.8544 (3) | 0.8519 (5) | 0.97141 (14) | 0.0308 (12) | |
C53 | 0.7807 (3) | 0.8944 (5) | 0.99139 (14) | 0.0269 (11) | |
C54 | 0.7175 (3) | 0.9294 (5) | 0.96558 (14) | 0.0283 (11) | |
C55 | 0.7506 (3) | 0.9078 (5) | 0.92894 (15) | 0.0306 (12) | |
H55A | 0.7235 | 0.9405 | 0.9049 | 0.037* | |
C56 | 0.8338 (3) | 0.8596 (5) | 0.93203 (15) | 0.0334 (12) | |
H56A | 0.8737 | 0.8533 | 0.9107 | 0.040* | |
C57 | 0.8388 (5) | 0.5107 (7) | 0.8775 (2) | 0.062 (2) | |
H57A | 0.8949 | 0.5530 | 0.8791 | 0.074* | |
H57B | 0.8019 | 0.5907 | 0.8675 | 0.074* | |
C58 | 0.8377 (4) | 0.3745 (6) | 0.85227 (17) | 0.0543 (16) | |
H58A | 0.8916 | 0.3612 | 0.8399 | 0.065* | |
H58B | 0.7953 | 0.3862 | 0.8325 | 0.065* | |
C59 | 0.8183 (4) | 0.2373 (6) | 0.87749 (15) | 0.0462 (14) | |
H59A | 0.7621 | 0.1993 | 0.8727 | 0.055* | |
H59B | 0.8577 | 0.1534 | 0.8730 | 0.055* | |
C60 | 0.8261 (4) | 0.2977 (6) | 0.91709 (16) | 0.0470 (15) | |
H60A | 0.7857 | 0.2477 | 0.9339 | 0.056* | |
H60B | 0.8818 | 0.2776 | 0.9271 | 0.056* | |
C61 | 0.8914 (3) | 0.4250 (6) | 1.00745 (16) | 0.0355 (12) | |
H61A | 0.9282 | 0.4932 | 1.0220 | 0.043* | |
H61B | 0.9122 | 0.4165 | 0.9813 | 0.043* | |
C62 | 0.8860 (3) | 0.2692 (6) | 1.02590 (16) | 0.0434 (14) | |
H62A | 0.9394 | 0.2385 | 1.0368 | 0.052* | |
H62B | 0.8680 | 0.1907 | 1.0076 | 0.052* | |
C63 | 0.8217 (3) | 0.2932 (6) | 1.05692 (15) | 0.0408 (13) | |
H63A | 0.8482 | 0.3076 | 1.0818 | 0.049* | |
H63B | 0.7839 | 0.2051 | 1.0584 | 0.049* | |
C64 | 0.7755 (3) | 0.4391 (7) | 1.04469 (14) | 0.0419 (13) | |
H64A | 0.7159 | 0.4191 | 1.0431 | 0.050* | |
H64B | 0.7849 | 0.5221 | 1.0632 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ca1 | 0.0204 (5) | 0.0258 (4) | 0.0308 (5) | −0.0008 (4) | 0.0022 (4) | −0.0010 (5) |
Ca2 | 0.0223 (5) | 0.0255 (4) | 0.0305 (5) | −0.0012 (4) | 0.0018 (4) | 0.0000 (5) |
O1 | 0.030 (2) | 0.042 (2) | 0.037 (3) | 0.0089 (16) | 0.0032 (18) | 0.0068 (17) |
O2 | 0.038 (2) | 0.0350 (19) | 0.034 (2) | 0.0083 (17) | 0.0047 (17) | −0.007 (2) |
O3 | 0.038 (2) | 0.042 (2) | 0.031 (2) | −0.0023 (18) | 0.0103 (16) | 0.000 (2) |
O4 | 0.0192 (19) | 0.051 (2) | 0.032 (3) | 0.0018 (15) | 0.0009 (16) | 0.0067 (17) |
C1 | 0.031 (3) | 0.037 (3) | 0.033 (3) | −0.006 (2) | 0.009 (2) | 0.000 (2) |
C2 | 0.034 (3) | 0.027 (3) | 0.037 (3) | −0.009 (2) | 0.000 (2) | 0.006 (2) |
C3 | 0.027 (3) | 0.022 (2) | 0.030 (3) | −0.0064 (19) | 0.001 (2) | 0.000 (2) |
C4 | 0.025 (3) | 0.023 (2) | 0.031 (3) | −0.005 (2) | −0.004 (2) | 0.000 (2) |
C5 | 0.024 (3) | 0.022 (2) | 0.041 (3) | −0.004 (2) | 0.005 (2) | 0.000 (2) |
C6 | 0.019 (3) | 0.038 (3) | 0.052 (4) | −0.003 (2) | −0.004 (2) | 0.001 (3) |
C7 | 0.028 (3) | 0.044 (3) | 0.064 (4) | −0.008 (3) | −0.015 (3) | 0.010 (3) |
C8 | 0.037 (3) | 0.043 (3) | 0.036 (3) | −0.006 (2) | −0.009 (2) | 0.003 (3) |
C9 | 0.028 (3) | 0.022 (2) | 0.037 (3) | −0.007 (2) | −0.003 (2) | −0.003 (2) |
C10 | 0.036 (3) | 0.044 (3) | 0.027 (3) | −0.004 (2) | 0.002 (2) | −0.005 (2) |
C11 | 0.033 (3) | 0.035 (3) | 0.042 (4) | 0.001 (2) | 0.011 (3) | −0.017 (3) |
C12 | 0.028 (3) | 0.027 (3) | 0.038 (4) | 0.007 (2) | 0.003 (2) | 0.000 (3) |
C13 | 0.018 (2) | 0.033 (2) | 0.040 (3) | 0.003 (2) | −0.002 (2) | 0.000 (2) |
C14 | 0.022 (3) | 0.039 (3) | 0.044 (4) | 0.002 (2) | −0.007 (2) | 0.006 (3) |
C15 | 0.022 (3) | 0.060 (4) | 0.035 (3) | 0.003 (2) | −0.008 (2) | 0.011 (3) |
C16 | 0.027 (3) | 0.051 (4) | 0.037 (3) | −0.002 (2) | −0.001 (2) | −0.009 (3) |
C17 | 0.038 (4) | 0.083 (6) | 0.039 (4) | 0.008 (3) | −0.007 (3) | −0.018 (3) |
C18 | 0.048 (4) | 0.065 (5) | 0.058 (5) | −0.002 (3) | −0.002 (3) | −0.032 (4) |
C19 | 0.038 (3) | 0.036 (3) | 0.069 (5) | 0.000 (3) | −0.002 (3) | −0.019 (3) |
C20 | 0.025 (3) | 0.042 (3) | 0.036 (4) | −0.003 (3) | −0.002 (2) | −0.005 (3) |
C21 | 0.018 (3) | 0.035 (3) | 0.043 (3) | −0.003 (2) | −0.002 (2) | −0.010 (3) |
C22 | 0.017 (2) | 0.030 (2) | 0.035 (3) | −0.0032 (19) | −0.001 (2) | 0.004 (2) |
C23 | 0.022 (3) | 0.038 (3) | 0.033 (3) | −0.010 (2) | −0.001 (2) | 0.003 (2) |
C24 | 0.020 (3) | 0.029 (3) | 0.064 (5) | −0.011 (2) | 0.001 (3) | 0.004 (3) |
C25 | 0.038 (3) | 0.051 (3) | 0.033 (3) | 0.004 (3) | 0.012 (3) | 0.009 (3) |
C26 | 0.043 (3) | 0.039 (3) | 0.054 (4) | −0.008 (3) | 0.005 (3) | 0.009 (3) |
C27 | 0.040 (3) | 0.034 (3) | 0.058 (4) | 0.003 (2) | 0.000 (3) | −0.004 (3) |
C28 | 0.025 (3) | 0.038 (3) | 0.042 (3) | 0.006 (2) | 0.001 (2) | 0.000 (2) |
C29 | 0.045 (3) | 0.031 (3) | 0.041 (3) | 0.007 (2) | 0.007 (3) | −0.005 (2) |
C30 | 0.054 (4) | 0.036 (3) | 0.041 (3) | 0.011 (3) | −0.003 (3) | −0.005 (3) |
C31 | 0.066 (4) | 0.049 (4) | 0.041 (3) | 0.002 (3) | 0.004 (3) | −0.008 (3) |
C32 | 0.088 (5) | 0.034 (4) | 0.054 (6) | −0.008 (3) | 0.030 (4) | −0.009 (3) |
C33 | 0.024 (3) | 0.043 (3) | 0.044 (4) | −0.008 (2) | 0.000 (2) | 0.005 (3) |
C34 | 0.020 (3) | 0.033 (3) | 0.040 (3) | −0.001 (2) | 0.007 (2) | 0.001 (2) |
C35 | 0.014 (2) | 0.028 (3) | 0.036 (3) | −0.0025 (19) | 0.004 (2) | −0.005 (2) |
C36 | 0.015 (2) | 0.039 (3) | 0.037 (3) | −0.007 (2) | −0.003 (2) | −0.005 (3) |
C37 | 0.019 (3) | 0.031 (3) | 0.060 (5) | −0.005 (2) | 0.003 (3) | −0.003 (3) |
C38 | 0.034 (3) | 0.035 (3) | 0.077 (5) | −0.003 (3) | −0.012 (3) | −0.015 (3) |
C39 | 0.044 (4) | 0.063 (5) | 0.061 (5) | 0.009 (3) | −0.012 (3) | −0.037 (4) |
C40 | 0.030 (3) | 0.070 (5) | 0.043 (4) | −0.002 (3) | −0.005 (3) | −0.009 (3) |
C41 | 0.023 (3) | 0.053 (4) | 0.035 (3) | −0.004 (2) | 0.002 (2) | −0.004 (3) |
C42 | 0.029 (3) | 0.048 (4) | 0.034 (3) | −0.002 (2) | −0.007 (2) | 0.008 (3) |
C43 | 0.029 (3) | 0.031 (3) | 0.051 (4) | 0.004 (2) | −0.001 (2) | 0.008 (3) |
C44 | 0.023 (3) | 0.028 (3) | 0.040 (3) | 0.003 (2) | 0.009 (2) | −0.001 (2) |
C45 | 0.030 (3) | 0.032 (3) | 0.040 (4) | 0.000 (2) | −0.001 (2) | −0.008 (3) |
C46 | 0.035 (3) | 0.040 (3) | 0.039 (4) | 0.003 (2) | 0.004 (3) | −0.011 (3) |
C47 | 0.042 (3) | 0.041 (3) | 0.034 (3) | −0.005 (3) | 0.009 (3) | −0.012 (3) |
C48 | 0.036 (3) | 0.029 (3) | 0.031 (3) | 0.000 (2) | −0.001 (2) | −0.001 (2) |
C49 | 0.052 (4) | 0.031 (3) | 0.031 (3) | −0.008 (3) | −0.006 (3) | −0.004 (2) |
C50 | 0.032 (3) | 0.038 (3) | 0.043 (4) | −0.004 (2) | −0.013 (3) | 0.006 (3) |
C51 | 0.026 (3) | 0.029 (3) | 0.059 (4) | −0.002 (2) | −0.002 (3) | 0.003 (3) |
C52 | 0.020 (3) | 0.026 (3) | 0.046 (3) | −0.007 (2) | 0.002 (2) | −0.003 (2) |
C53 | 0.024 (3) | 0.024 (2) | 0.033 (3) | −0.004 (2) | 0.001 (2) | −0.005 (2) |
C54 | 0.029 (3) | 0.024 (3) | 0.031 (3) | −0.0019 (19) | 0.003 (2) | −0.003 (2) |
C55 | 0.038 (3) | 0.027 (3) | 0.026 (3) | −0.003 (2) | 0.002 (2) | 0.003 (2) |
C56 | 0.025 (3) | 0.035 (3) | 0.040 (3) | −0.005 (2) | 0.007 (2) | −0.003 (2) |
C57 | 0.106 (6) | 0.051 (5) | 0.029 (5) | 0.001 (3) | 0.021 (4) | 0.003 (3) |
C58 | 0.073 (4) | 0.048 (3) | 0.042 (4) | −0.002 (3) | 0.012 (3) | −0.004 (3) |
C59 | 0.053 (4) | 0.042 (3) | 0.045 (3) | 0.000 (3) | −0.004 (3) | −0.008 (3) |
C60 | 0.060 (4) | 0.035 (3) | 0.047 (4) | 0.009 (3) | 0.001 (3) | −0.001 (3) |
C61 | 0.028 (3) | 0.041 (3) | 0.037 (3) | 0.000 (2) | −0.001 (2) | −0.002 (3) |
C62 | 0.038 (3) | 0.044 (3) | 0.048 (4) | 0.002 (3) | 0.001 (3) | 0.002 (3) |
C63 | 0.046 (3) | 0.031 (3) | 0.046 (3) | −0.001 (2) | 0.010 (3) | 0.003 (2) |
C64 | 0.039 (3) | 0.053 (3) | 0.034 (3) | 0.004 (3) | −0.003 (2) | −0.003 (3) |
Ca1—O1 | 2.346 (4) | C27—C28 | 1.516 (7) |
Ca1—O2 | 2.357 (4) | C27—H27A | 0.9800 |
Ca1—C23 | 2.671 (5) | C27—H27B | 0.9800 |
Ca1—C4 | 2.699 (4) | C28—H28A | 0.9800 |
Ca1—C3 | 2.709 (4) | C28—H28B | 0.9800 |
Ca1—C24 | 2.709 (5) | C29—C30 | 1.515 (7) |
Ca1—C2 | 2.715 (5) | C29—H29A | 0.9800 |
Ca1—C1 | 2.726 (5) | C29—H29B | 0.9800 |
Ca1—C22 | 2.739 (4) | C30—C31 | 1.512 (7) |
Ca1—C5 | 2.744 (5) | C30—H30A | 0.9800 |
Ca1—C21 | 2.748 (5) | C30—H30B | 0.9800 |
Ca1—C20 | 2.756 (6) | C31—C32 | 1.528 (8) |
Ca2—O4 | 2.351 (4) | C31—H31A | 0.9800 |
Ca2—O3 | 2.354 (4) | C31—H31B | 0.9800 |
Ca2—C33 | 2.686 (5) | C32—H32A | 0.9800 |
Ca2—C34 | 2.692 (5) | C32—H32B | 0.9800 |
Ca2—C53 | 2.705 (4) | C33—C34 | 1.406 (7) |
Ca2—C55 | 2.707 (5) | C33—C37 | 1.427 (8) |
Ca2—C54 | 2.713 (5) | C33—H33A | 0.9900 |
Ca2—C56 | 2.722 (5) | C34—C35 | 1.415 (7) |
Ca2—C35 | 2.742 (4) | C34—H34A | 0.9900 |
Ca2—C52 | 2.745 (4) | C35—C36 | 1.414 (7) |
Ca2—C36 | 2.761 (5) | C35—C44 | 1.511 (6) |
Ca2—C37 | 2.762 (5) | C36—C41 | 1.420 (7) |
O1—C28 | 1.448 (6) | C36—C37 | 1.446 (7) |
O1—C25 | 1.453 (6) | C37—C38 | 1.410 (8) |
O2—C32 | 1.397 (8) | C38—C39 | 1.364 (9) |
O2—C29 | 1.464 (6) | C38—H38A | 0.9400 |
O3—C60 | 1.442 (6) | C39—C40 | 1.401 (9) |
O3—C57 | 1.463 (8) | C39—H39A | 0.9400 |
O4—C64 | 1.438 (7) | C40—C41 | 1.368 (8) |
O4—C61 | 1.444 (6) | C40—H40A | 0.9400 |
C1—C5 | 1.415 (7) | C41—C42 | 1.463 (8) |
C1—C2 | 1.422 (7) | C42—C43 | 1.341 (7) |
C1—H1A | 0.9900 | C42—H42A | 0.9400 |
C2—C3 | 1.412 (7) | C43—C44 | 1.512 (7) |
C2—H2A | 0.9900 | C43—H43A | 0.9400 |
C3—C4 | 1.407 (6) | C44—C45 | 1.559 (7) |
C3—C12 | 1.511 (7) | C44—H44A | 0.9900 |
C4—C9 | 1.419 (6) | C45—C46 | 1.524 (9) |
C4—C5 | 1.428 (7) | C45—C54 | 1.532 (7) |
C5—C6 | 1.418 (7) | C45—H45A | 0.9900 |
C6—C7 | 1.366 (7) | C46—C47 | 1.339 (8) |
C6—H6A | 0.9400 | C46—H46A | 0.9400 |
C7—C8 | 1.424 (7) | C47—C48 | 1.469 (7) |
C7—H7A | 0.9400 | C47—H47A | 0.9400 |
C8—C9 | 1.374 (7) | C48—C49 | 1.371 (7) |
C8—H8A | 0.9400 | C48—C53 | 1.405 (7) |
C9—C10 | 1.444 (7) | C49—C50 | 1.421 (7) |
C10—C11 | 1.338 (7) | C49—H49A | 0.9400 |
C10—H10A | 0.9400 | C50—C51 | 1.356 (7) |
C11—C12 | 1.501 (8) | C50—H50A | 0.9400 |
C11—H11A | 0.9400 | C51—C52 | 1.422 (7) |
C12—C13 | 1.586 (7) | C51—H51A | 0.9400 |
C12—H12A | 0.9900 | C52—C56 | 1.421 (7) |
C13—C22 | 1.510 (6) | C52—C53 | 1.430 (6) |
C13—C14 | 1.512 (7) | C53—C54 | 1.397 (7) |
C13—H13A | 0.9900 | C54—C55 | 1.404 (7) |
C14—C15 | 1.329 (7) | C55—C56 | 1.411 (7) |
C14—H14A | 0.9400 | C55—H55A | 0.9900 |
C15—C16 | 1.455 (7) | C56—H56A | 0.9900 |
C15—H15A | 0.9400 | C57—C58 | 1.477 (8) |
C16—C17 | 1.385 (8) | C57—H57A | 0.9800 |
C16—C21 | 1.395 (8) | C57—H57B | 0.9800 |
C17—C18 | 1.414 (10) | C58—C59 | 1.515 (7) |
C17—H17A | 0.9400 | C58—H58A | 0.9800 |
C18—C19 | 1.377 (9) | C58—H58B | 0.9800 |
C18—H18A | 0.9400 | C59—C60 | 1.489 (7) |
C19—C20 | 1.428 (8) | C59—H59A | 0.9800 |
C19—H19A | 0.9400 | C59—H59B | 0.9800 |
C20—C21 | 1.414 (7) | C60—H60A | 0.9800 |
C20—C24 | 1.419 (7) | C60—H60B | 0.9800 |
C21—C22 | 1.403 (7) | C61—C62 | 1.502 (7) |
C22—C23 | 1.411 (7) | C61—H61A | 0.9800 |
C23—C24 | 1.410 (8) | C61—H61B | 0.9800 |
C23—H23A | 0.9900 | C62—C63 | 1.518 (7) |
C24—H24A | 0.9900 | C62—H62A | 0.9800 |
C25—C26 | 1.511 (7) | C62—H62B | 0.9800 |
C25—H25A | 0.9800 | C63—C64 | 1.531 (7) |
C25—H25B | 0.9800 | C63—H63A | 0.9800 |
C26—C27 | 1.536 (7) | C63—H63B | 0.9800 |
C26—H26A | 0.9800 | C64—H64A | 0.9800 |
C26—H26B | 0.9800 | C64—H64B | 0.9800 |
O1—Ca1—O2 | 87.93 (13) | C22—C23—H23A | 124.0 |
O1—Ca1—C23 | 91.21 (15) | Ca1—C23—H23A | 124.0 |
O2—Ca1—C23 | 132.79 (15) | C23—C24—C20 | 106.6 (6) |
O1—Ca1—C4 | 90.61 (14) | C23—C24—Ca1 | 73.3 (3) |
O2—Ca1—C4 | 132.40 (14) | C20—C24—Ca1 | 76.8 (4) |
C23—Ca1—C4 | 94.80 (15) | C23—C24—H24A | 126.0 |
O1—Ca1—C3 | 119.11 (15) | C20—C24—H24A | 126.0 |
O2—Ca1—C3 | 135.45 (15) | Ca1—C24—H24A | 126.0 |
C23—Ca1—C3 | 84.59 (15) | O1—C25—C26 | 105.0 (4) |
O1—Ca1—C24 | 83.94 (16) | O1—C25—H25A | 110.8 |
O2—Ca1—C24 | 102.92 (16) | C26—C25—H25A | 110.8 |
C4—Ca1—C24 | 124.22 (16) | O1—C25—H25B | 110.8 |
C3—Ca1—C24 | 113.89 (16) | C26—C25—H25B | 110.8 |
O1—Ca1—C2 | 135.85 (15) | H25A—C25—H25B | 108.8 |
O2—Ca1—C2 | 105.72 (15) | C25—C26—C27 | 104.6 (4) |
C23—Ca1—C2 | 107.26 (16) | C25—C26—H26A | 110.8 |
C24—Ca1—C2 | 130.61 (17) | C27—C26—H26A | 110.8 |
O1—Ca1—C1 | 112.57 (14) | C25—C26—H26B | 110.8 |
O2—Ca1—C1 | 87.75 (15) | C27—C26—H26B | 110.8 |
C23—Ca1—C1 | 134.79 (15) | H26A—C26—H26B | 108.9 |
C3—Ca1—C1 | 50.41 (14) | C28—C27—C26 | 104.0 (4) |
C24—Ca1—C1 | 160.91 (16) | C28—C27—H27A | 111.0 |
O1—Ca1—C22 | 120.78 (15) | C26—C27—H27A | 111.0 |
O2—Ca1—C22 | 132.00 (15) | C28—C27—H27B | 111.0 |
C4—Ca1—C22 | 88.26 (14) | C26—C27—H27B | 111.0 |
C3—Ca1—C22 | 66.10 (13) | H27A—C27—H27B | 109.0 |
C24—Ca1—C22 | 50.44 (15) | O1—C28—C27 | 104.4 (4) |
C2—Ca1—C22 | 80.72 (14) | O1—C28—H28A | 110.9 |
C1—Ca1—C22 | 110.80 (14) | C27—C28—H28A | 110.9 |
O1—Ca1—C5 | 86.72 (13) | O1—C28—H28B | 110.9 |
O2—Ca1—C5 | 102.09 (14) | C27—C28—H28B | 110.9 |
C23—Ca1—C5 | 124.99 (15) | H28A—C28—H28B | 108.9 |
C3—Ca1—C5 | 50.55 (14) | O2—C29—C30 | 104.7 (4) |
C24—Ca1—C5 | 152.91 (16) | O2—C29—H29A | 110.8 |
C22—Ca1—C5 | 116.01 (14) | C30—C29—H29A | 110.8 |
O1—Ca1—C21 | 133.26 (16) | O2—C29—H29B | 110.8 |
O2—Ca1—C21 | 102.47 (14) | C30—C29—H29B | 110.8 |
C4—Ca1—C21 | 112.50 (15) | H29A—C29—H29B | 108.9 |
C3—Ca1—C21 | 84.57 (15) | C31—C30—C29 | 105.4 (4) |
C2—Ca1—C21 | 85.38 (16) | C31—C30—H30A | 110.7 |
C1—Ca1—C21 | 113.27 (16) | C29—C30—H30A | 110.7 |
C5—Ca1—C21 | 133.19 (15) | C31—C30—H30B | 110.7 |
O1—Ca1—C20 | 108.49 (16) | C29—C30—H30B | 110.7 |
O2—Ca1—C20 | 86.51 (16) | H30A—C30—H30B | 108.8 |
C4—Ca1—C20 | 138.05 (16) | C30—C31—C32 | 103.9 (5) |
C3—Ca1—C20 | 113.34 (17) | C30—C31—H31A | 111.0 |
C2—Ca1—C20 | 113.99 (17) | C32—C31—H31A | 111.0 |
C1—Ca1—C20 | 138.26 (17) | C30—C31—H31B | 111.0 |
C5—Ca1—C20 | 162.95 (16) | C32—C31—H31B | 111.0 |
O4—Ca2—O3 | 87.39 (14) | H31A—C31—H31B | 109.0 |
O4—Ca2—C33 | 83.52 (16) | O2—C32—C31 | 108.3 (5) |
O3—Ca2—C33 | 103.40 (16) | O2—C32—H32A | 110.0 |
O4—Ca2—C34 | 91.39 (15) | C31—C32—H32A | 110.0 |
O3—Ca2—C34 | 133.13 (15) | O2—C32—H32B | 110.0 |
O4—Ca2—C53 | 92.25 (14) | C31—C32—H32B | 110.0 |
O3—Ca2—C53 | 132.74 (14) | H32A—C32—H32B | 108.4 |
C33—Ca2—C53 | 123.54 (17) | C34—C33—C37 | 109.2 (6) |
C34—Ca2—C53 | 94.13 (15) | C34—C33—Ca2 | 75.1 (3) |
O4—Ca2—C55 | 136.99 (15) | C37—C33—Ca2 | 77.8 (3) |
O3—Ca2—C55 | 105.19 (14) | C34—C33—H33A | 124.7 |
C33—Ca2—C55 | 130.41 (17) | C37—C33—H33A | 124.7 |
C34—Ca2—C55 | 107.14 (15) | Ca2—C33—H33A | 124.7 |
O4—Ca2—C54 | 120.68 (15) | C33—C34—C35 | 109.3 (5) |
O3—Ca2—C54 | 134.80 (15) | C33—C34—Ca2 | 74.6 (3) |
C33—Ca2—C54 | 113.66 (17) | C35—C34—Ca2 | 76.9 (3) |
C34—Ca2—C54 | 84.48 (15) | C33—C34—H34A | 124.8 |
O4—Ca2—C56 | 113.27 (14) | C35—C34—H34A | 124.8 |
O3—Ca2—C56 | 87.74 (14) | Ca2—C34—H34A | 124.8 |
C33—Ca2—C56 | 160.54 (17) | C36—C35—C34 | 106.4 (4) |
C34—Ca2—C56 | 134.32 (15) | C36—C35—C44 | 119.8 (5) |
C54—Ca2—C56 | 50.01 (14) | C34—C35—C44 | 133.8 (5) |
O4—Ca2—C35 | 121.12 (14) | C36—C35—Ca2 | 75.8 (3) |
O3—Ca2—C35 | 131.64 (14) | C34—C35—Ca2 | 73.0 (3) |
C33—Ca2—C35 | 50.15 (16) | C44—C35—Ca2 | 116.1 (3) |
C53—Ca2—C35 | 87.78 (14) | C35—C36—C41 | 126.6 (5) |
C55—Ca2—C35 | 80.76 (15) | C35—C36—C37 | 110.0 (5) |
C54—Ca2—C35 | 66.14 (14) | C41—C36—C37 | 123.4 (5) |
C56—Ca2—C35 | 110.63 (14) | C35—C36—Ca2 | 74.4 (3) |
O4—Ca2—C52 | 87.61 (14) | C41—C36—Ca2 | 118.4 (3) |
O3—Ca2—C52 | 102.50 (14) | C37—C36—Ca2 | 74.9 (3) |
C33—Ca2—C52 | 152.16 (16) | C38—C37—C33 | 139.3 (6) |
C34—Ca2—C52 | 124.27 (15) | C38—C37—C36 | 115.6 (6) |
C54—Ca2—C52 | 50.33 (14) | C33—C37—C36 | 105.1 (6) |
C35—Ca2—C52 | 115.72 (14) | C38—C37—Ca2 | 118.3 (4) |
O4—Ca2—C36 | 133.00 (15) | C33—C37—Ca2 | 71.9 (3) |
O3—Ca2—C36 | 101.96 (15) | C36—C37—Ca2 | 74.8 (3) |
C53—Ca2—C36 | 112.03 (15) | C39—C38—C37 | 120.1 (6) |
C55—Ca2—C36 | 85.24 (16) | C39—C38—H38A | 119.9 |
C54—Ca2—C36 | 84.47 (15) | C37—C38—H38A | 119.9 |
C56—Ca2—C36 | 113.04 (16) | C38—C39—C40 | 123.5 (5) |
C52—Ca2—C36 | 133.00 (16) | C38—C39—H39A | 118.3 |
O4—Ca2—C37 | 107.35 (16) | C40—C39—H39A | 118.3 |
O3—Ca2—C37 | 85.84 (16) | C41—C40—C39 | 120.0 (6) |
C34—Ca2—C37 | 50.06 (18) | C41—C40—H40A | 120.0 |
C53—Ca2—C37 | 138.14 (16) | C39—C40—H40A | 120.0 |
C55—Ca2—C37 | 114.36 (18) | C40—C41—C36 | 117.4 (5) |
C54—Ca2—C37 | 113.86 (16) | C40—C41—C42 | 128.4 (5) |
C56—Ca2—C37 | 138.48 (17) | C36—C41—C42 | 114.1 (5) |
C35—Ca2—C37 | 50.38 (16) | C43—C42—C41 | 121.8 (5) |
C52—Ca2—C37 | 163.35 (17) | C43—C42—H42A | 119.1 |
C28—O1—C25 | 103.8 (4) | C41—C42—H42A | 119.1 |
C28—O1—Ca1 | 127.2 (3) | C42—C43—C44 | 126.8 (5) |
C25—O1—Ca1 | 129.0 (3) | C42—C43—H43A | 116.6 |
C32—O2—C29 | 106.3 (4) | C44—C43—H43A | 116.6 |
C32—O2—Ca1 | 125.9 (3) | C35—C44—C43 | 110.6 (4) |
C29—O2—Ca1 | 127.7 (3) | C35—C44—C45 | 113.7 (4) |
C60—O3—C57 | 106.0 (4) | C43—C44—C45 | 109.8 (4) |
C60—O3—Ca2 | 129.3 (3) | C35—C44—H44A | 107.5 |
C57—O3—Ca2 | 124.3 (3) | C43—C44—H44A | 107.5 |
C64—O4—C61 | 104.9 (4) | C45—C44—H44A | 107.5 |
C64—O4—Ca2 | 128.5 (3) | C46—C45—C54 | 109.9 (5) |
C61—O4—Ca2 | 126.5 (3) | C46—C45—C44 | 111.0 (5) |
C5—C1—C2 | 107.9 (4) | C54—C45—C44 | 113.2 (4) |
C5—C1—Ca1 | 75.7 (3) | C46—C45—H45A | 107.5 |
C2—C1—Ca1 | 74.4 (3) | C54—C45—H45A | 107.5 |
C5—C1—H1A | 125.5 | C44—C45—H45A | 107.5 |
C2—C1—H1A | 125.5 | C47—C46—C45 | 126.3 (5) |
Ca1—C1—H1A | 125.5 | C47—C46—H46A | 116.9 |
C3—C2—C1 | 109.5 (5) | C45—C46—H46A | 116.9 |
C3—C2—Ca1 | 74.7 (3) | C46—C47—C48 | 122.2 (5) |
C1—C2—Ca1 | 75.3 (3) | C46—C47—H47A | 118.9 |
C3—C2—H2A | 124.9 | C48—C47—H47A | 118.9 |
C1—C2—H2A | 124.9 | C49—C48—C53 | 118.1 (5) |
Ca1—C2—H2A | 124.9 | C49—C48—C47 | 127.6 (5) |
C4—C3—C2 | 106.0 (4) | C53—C48—C47 | 114.2 (4) |
C4—C3—C12 | 119.7 (5) | C48—C49—C50 | 120.0 (5) |
C2—C3—C12 | 134.4 (5) | C48—C49—H49A | 120.0 |
C4—C3—Ca1 | 74.6 (3) | C50—C49—H49A | 120.0 |
C2—C3—Ca1 | 75.1 (3) | C51—C50—C49 | 122.5 (5) |
C12—C3—Ca1 | 115.0 (3) | C51—C50—H50A | 118.7 |
C3—C4—C9 | 126.5 (4) | C49—C50—H50A | 118.7 |
C3—C4—C5 | 110.4 (4) | C50—C51—C52 | 119.5 (5) |
C9—C4—C5 | 123.0 (4) | C50—C51—H51A | 120.2 |
C3—C4—Ca1 | 75.3 (2) | C52—C51—H51A | 120.2 |
C9—C4—Ca1 | 113.4 (3) | C56—C52—C51 | 137.2 (5) |
C5—C4—Ca1 | 76.5 (3) | C56—C52—C53 | 105.6 (4) |
C1—C5—C6 | 136.5 (5) | C51—C52—C53 | 117.2 (5) |
C1—C5—C4 | 106.2 (4) | C56—C52—Ca2 | 74.0 (3) |
C6—C5—C4 | 117.3 (4) | C51—C52—Ca2 | 116.8 (3) |
C1—C5—Ca1 | 74.3 (3) | C53—C52—Ca2 | 73.2 (2) |
C6—C5—Ca1 | 116.8 (3) | C54—C53—C48 | 127.1 (5) |
C4—C5—Ca1 | 73.1 (2) | C54—C53—C52 | 110.3 (4) |
C7—C6—C5 | 119.3 (5) | C48—C53—C52 | 122.5 (5) |
C7—C6—H6A | 120.3 | C54—C53—Ca2 | 75.4 (3) |
C5—C6—H6A | 120.3 | C48—C53—Ca2 | 114.6 (3) |
C6—C7—C8 | 122.7 (5) | C52—C53—Ca2 | 76.3 (2) |
C6—C7—H7A | 118.7 | C53—C54—C55 | 106.5 (4) |
C8—C7—H7A | 118.7 | C53—C54—C45 | 120.3 (5) |
C9—C8—C7 | 120.1 (5) | C55—C54—C45 | 133.2 (5) |
C9—C8—H8A | 119.9 | C53—C54—Ca2 | 74.7 (3) |
C7—C8—H8A | 119.9 | C55—C54—Ca2 | 74.8 (3) |
C8—C9—C4 | 117.4 (4) | C45—C54—Ca2 | 115.0 (3) |
C8—C9—C10 | 128.5 (5) | C54—C55—C56 | 109.4 (5) |
C4—C9—C10 | 114.1 (4) | C54—C55—Ca2 | 75.2 (3) |
C11—C10—C9 | 122.4 (5) | C56—C55—Ca2 | 75.5 (3) |
C11—C10—H10A | 118.8 | C54—C55—H55A | 124.8 |
C9—C10—H10A | 118.8 | C56—C55—H55A | 124.8 |
C10—C11—C12 | 126.5 (5) | Ca2—C55—H55A | 124.8 |
C10—C11—H11A | 116.8 | C55—C56—C52 | 108.2 (4) |
C12—C11—H11A | 116.8 | C55—C56—Ca2 | 74.3 (3) |
C11—C12—C3 | 110.7 (4) | C52—C56—Ca2 | 75.8 (3) |
C11—C12—C13 | 109.9 (4) | C55—C56—H56A | 125.4 |
C3—C12—C13 | 112.6 (4) | C52—C56—H56A | 125.4 |
C11—C12—H12A | 107.8 | Ca2—C56—H56A | 125.4 |
C3—C12—H12A | 107.8 | O3—C57—C58 | 107.6 (5) |
C13—C12—H12A | 107.8 | O3—C57—H57A | 110.2 |
C22—C13—C14 | 110.4 (4) | C58—C57—H57A | 110.2 |
C22—C13—C12 | 112.5 (4) | O3—C57—H57B | 110.2 |
C14—C13—C12 | 110.0 (4) | C58—C57—H57B | 110.2 |
C22—C13—H13A | 107.9 | H57A—C57—H57B | 108.5 |
C14—C13—H13A | 107.9 | C57—C58—C59 | 106.4 (5) |
C12—C13—H13A | 107.9 | C57—C58—H58A | 110.5 |
C15—C14—C13 | 126.3 (5) | C59—C58—H58A | 110.5 |
C15—C14—H14A | 116.8 | C57—C58—H58B | 110.5 |
C13—C14—H14A | 116.8 | C59—C58—H58B | 110.5 |
C14—C15—C16 | 121.3 (5) | H58A—C58—H58B | 108.6 |
C14—C15—H15A | 119.3 | C60—C59—C58 | 104.5 (4) |
C16—C15—H15A | 119.3 | C60—C59—H59A | 110.9 |
C17—C16—C21 | 116.7 (5) | C58—C59—H59A | 110.9 |
C17—C16—C15 | 127.4 (6) | C60—C59—H59B | 110.9 |
C21—C16—C15 | 115.9 (5) | C58—C59—H59B | 110.9 |
C16—C17—C18 | 120.6 (6) | H59A—C59—H59B | 108.9 |
C16—C17—H17A | 119.7 | O3—C60—C59 | 106.9 (4) |
C18—C17—H17A | 119.7 | O3—C60—H60A | 110.3 |
C19—C18—C17 | 123.0 (6) | C59—C60—H60A | 110.3 |
C19—C18—H18A | 118.5 | O3—C60—H60B | 110.3 |
C17—C18—H18A | 118.5 | C59—C60—H60B | 110.3 |
C18—C19—C20 | 117.7 (6) | H60A—C60—H60B | 108.6 |
C18—C19—H19A | 121.1 | O4—C61—C62 | 104.4 (4) |
C20—C19—H19A | 121.1 | O4—C61—H61A | 110.9 |
C21—C20—C24 | 107.1 (6) | C62—C61—H61A | 110.9 |
C21—C20—C19 | 118.0 (5) | O4—C61—H61B | 110.9 |
C24—C20—C19 | 135.0 (6) | C62—C61—H61B | 110.9 |
C21—C20—Ca1 | 74.8 (3) | H61A—C61—H61B | 108.9 |
C24—C20—Ca1 | 73.1 (3) | C61—C62—C63 | 103.0 (4) |
C19—C20—Ca1 | 118.0 (4) | C61—C62—H62A | 111.2 |
C16—C21—C22 | 125.4 (5) | C63—C62—H62A | 111.2 |
C16—C21—C20 | 124.1 (5) | C61—C62—H62B | 111.2 |
C22—C21—C20 | 110.5 (5) | C63—C62—H62B | 111.2 |
C16—C21—Ca1 | 117.8 (3) | H62A—C62—H62B | 109.1 |
C22—C21—Ca1 | 74.8 (3) | C62—C63—C64 | 104.3 (4) |
C20—C21—Ca1 | 75.4 (3) | C62—C63—H63A | 110.9 |
C21—C22—C23 | 105.2 (4) | C64—C63—H63A | 110.9 |
C21—C22—C13 | 120.5 (5) | C62—C63—H63B | 110.9 |
C23—C22—C13 | 134.3 (5) | C64—C63—H63B | 110.9 |
C21—C22—Ca1 | 75.5 (3) | H63A—C63—H63B | 108.9 |
C23—C22—Ca1 | 72.2 (3) | O4—C64—C63 | 106.9 (4) |
C13—C22—Ca1 | 116.1 (3) | O4—C64—H64A | 110.3 |
C24—C23—C22 | 110.7 (5) | C63—C64—H64A | 110.3 |
C24—C23—Ca1 | 76.3 (3) | O4—C64—H64B | 110.3 |
C22—C23—Ca1 | 77.6 (3) | C63—C64—H64B | 110.3 |
C24—C23—H23A | 124.0 | H64A—C64—H64B | 108.6 |
O2—Ca1—O1—C28 | −33.6 (4) | C21—Ca1—C23—C22 | 37.8 (3) |
C23—Ca1—O1—C28 | −166.4 (4) | C20—Ca1—C23—C22 | 77.5 (3) |
C4—Ca1—O1—C28 | 98.8 (4) | C22—C23—C24—C20 | −0.5 (6) |
C3—Ca1—O1—C28 | 109.2 (4) | Ca1—C23—C24—C20 | 70.3 (4) |
C24—Ca1—O1—C28 | −136.8 (4) | C22—C23—C24—Ca1 | −70.8 (3) |
C2—Ca1—O1—C28 | 77.0 (4) | C21—C20—C24—C23 | −0.2 (6) |
C1—Ca1—O1—C28 | 53.1 (4) | C19—C20—C24—C23 | 179.2 (6) |
C22—Ca1—O1—C28 | −172.8 (3) | Ca1—C20—C24—C23 | −67.9 (3) |
C5—Ca1—O1—C28 | 68.7 (4) | C21—C20—C24—Ca1 | 67.7 (4) |
C21—Ca1—O1—C28 | −138.8 (4) | C19—C20—C24—Ca1 | −113.0 (7) |
C20—Ca1—O1—C28 | −119.2 (4) | O1—Ca1—C24—C23 | −102.9 (3) |
O2—Ca1—O1—C25 | 146.0 (4) | O2—Ca1—C24—C23 | 170.7 (3) |
C23—Ca1—O1—C25 | 13.2 (4) | C4—Ca1—C24—C23 | −16.3 (4) |
C4—Ca1—O1—C25 | −81.6 (4) | C3—Ca1—C24—C23 | 16.3 (4) |
C3—Ca1—O1—C25 | −71.3 (4) | C2—Ca1—C24—C23 | 46.4 (4) |
C24—Ca1—O1—C25 | 42.7 (4) | C1—Ca1—C24—C23 | 48.0 (7) |
C2—Ca1—O1—C25 | −103.4 (4) | C22—Ca1—C24—C23 | 36.2 (3) |
C1—Ca1—O1—C25 | −127.3 (4) | C5—Ca1—C24—C23 | −32.4 (6) |
C22—Ca1—O1—C25 | 6.7 (5) | C21—Ca1—C24—C23 | 75.2 (3) |
C5—Ca1—O1—C25 | −111.8 (4) | C20—Ca1—C24—C23 | 112.1 (5) |
C21—Ca1—O1—C25 | 40.7 (5) | O1—Ca1—C24—C20 | 145.1 (4) |
C20—Ca1—O1—C25 | 60.3 (5) | O2—Ca1—C24—C20 | 58.6 (4) |
O1—Ca1—O2—C32 | 141.7 (5) | C23—Ca1—C24—C20 | −112.1 (5) |
C23—Ca1—O2—C32 | −128.6 (5) | C4—Ca1—C24—C20 | −128.3 (4) |
C4—Ca1—O2—C32 | 52.8 (6) | C3—Ca1—C24—C20 | −95.7 (4) |
C3—Ca1—O2—C32 | 10.6 (6) | C2—Ca1—C24—C20 | −65.7 (4) |
C24—Ca1—O2—C32 | −135.0 (5) | C1—Ca1—C24—C20 | −64.1 (7) |
C2—Ca1—O2—C32 | 4.3 (6) | C22—Ca1—C24—C20 | −75.9 (4) |
C1—Ca1—O2—C32 | 29.0 (5) | C5—Ca1—C24—C20 | −144.4 (4) |
C22—Ca1—O2—C32 | −87.3 (5) | C21—Ca1—C24—C20 | −36.9 (3) |
C5—Ca1—O2—C32 | 55.5 (5) | C28—O1—C25—C26 | 40.5 (5) |
C21—Ca1—O2—C32 | −84.3 (5) | Ca1—O1—C25—C26 | −139.1 (4) |
C20—Ca1—O2—C32 | −109.6 (5) | O1—C25—C26—C27 | −22.5 (6) |
O1—Ca1—O2—C29 | −41.7 (4) | C25—C26—C27—C28 | −2.9 (6) |
C23—Ca1—O2—C29 | 48.0 (5) | C25—O1—C28—C27 | −42.4 (5) |
C4—Ca1—O2—C29 | −130.6 (4) | Ca1—O1—C28—C27 | 137.2 (4) |
C3—Ca1—O2—C29 | −172.8 (4) | C26—C27—C28—O1 | 27.3 (6) |
C24—Ca1—O2—C29 | 41.6 (4) | C32—O2—C29—C30 | 34.7 (6) |
C2—Ca1—O2—C29 | −179.1 (4) | Ca1—O2—C29—C30 | −142.4 (4) |
C1—Ca1—O2—C29 | −154.4 (4) | O2—C29—C30—C31 | −25.4 (6) |
C22—Ca1—O2—C29 | 89.3 (4) | C29—C30—C31—C32 | 7.8 (7) |
C5—Ca1—O2—C29 | −127.9 (4) | C29—O2—C32—C31 | −30.3 (7) |
C21—Ca1—O2—C29 | 92.2 (4) | Ca1—O2—C32—C31 | 146.9 (4) |
C20—Ca1—O2—C29 | 67.0 (4) | C30—C31—C32—O2 | 13.5 (8) |
O4—Ca2—O3—C60 | 40.6 (4) | O4—Ca2—C33—C34 | 104.0 (3) |
C33—Ca2—O3—C60 | −42.1 (4) | O3—Ca2—C33—C34 | −170.2 (3) |
C34—Ca2—O3—C60 | −48.9 (5) | C53—Ca2—C33—C34 | 15.6 (4) |
C53—Ca2—O3—C60 | 131.2 (4) | C55—Ca2—C33—C34 | −46.4 (4) |
C55—Ca2—O3—C60 | 178.8 (4) | C54—Ca2—C33—C34 | −16.7 (4) |
C54—Ca2—O3—C60 | 173.0 (4) | C56—Ca2—C33—C34 | −46.7 (6) |
C56—Ca2—O3—C60 | 154.0 (4) | C35—Ca2—C33—C34 | −36.5 (3) |
C35—Ca2—O3—C60 | −90.1 (4) | C52—Ca2—C33—C34 | 31.8 (6) |
C52—Ca2—O3—C60 | 127.6 (4) | C36—Ca2—C33—C34 | −75.8 (4) |
C36—Ca2—O3—C60 | −92.9 (4) | C37—Ca2—C33—C34 | −113.9 (5) |
C37—Ca2—O3—C60 | −67.0 (4) | O4—Ca2—C33—C37 | −142.1 (4) |
O4—Ca2—O3—C57 | −147.3 (5) | O3—Ca2—C33—C37 | −56.3 (4) |
C33—Ca2—O3—C57 | 130.0 (5) | C34—Ca2—C33—C37 | 113.9 (5) |
C34—Ca2—O3—C57 | 123.2 (5) | C53—Ca2—C33—C37 | 129.5 (3) |
C53—Ca2—O3—C57 | −56.7 (6) | C55—Ca2—C33—C37 | 67.5 (4) |
C55—Ca2—O3—C57 | −9.1 (5) | C54—Ca2—C33—C37 | 97.2 (4) |
C54—Ca2—O3—C57 | −14.9 (6) | C56—Ca2—C33—C37 | 67.2 (7) |
C56—Ca2—O3—C57 | −33.9 (5) | C35—Ca2—C33—C37 | 77.4 (4) |
C35—Ca2—O3—C57 | 82.0 (5) | C52—Ca2—C33—C37 | 145.7 (4) |
C52—Ca2—O3—C57 | −60.4 (5) | C36—Ca2—C33—C37 | 38.1 (3) |
C36—Ca2—O3—C57 | 79.2 (5) | C37—C33—C34—C35 | −1.4 (6) |
C37—Ca2—O3—C57 | 105.1 (5) | Ca2—C33—C34—C35 | 69.7 (3) |
O3—Ca2—O4—C64 | −143.9 (4) | C37—C33—C34—Ca2 | −71.1 (4) |
C33—Ca2—O4—C64 | −40.1 (4) | O4—Ca2—C34—C33 | −74.6 (3) |
C34—Ca2—O4—C64 | −10.8 (4) | O3—Ca2—C34—C33 | 13.1 (4) |
C53—Ca2—O4—C64 | 83.4 (4) | C53—Ca2—C34—C33 | −167.0 (3) |
C55—Ca2—O4—C64 | 106.5 (4) | C55—Ca2—C34—C33 | 144.8 (3) |
C54—Ca2—O4—C64 | 73.6 (4) | C54—Ca2—C34—C33 | 164.7 (3) |
C56—Ca2—O4—C64 | 129.7 (4) | C56—Ca2—C34—C33 | 160.2 (3) |
C35—Ca2—O4—C64 | −5.3 (5) | C35—Ca2—C34—C33 | 114.6 (5) |
C52—Ca2—O4—C64 | 113.5 (4) | C52—Ca2—C34—C33 | −162.7 (3) |
C36—Ca2—O4—C64 | −39.9 (5) | C36—Ca2—C34—C33 | 77.2 (4) |
C37—Ca2—O4—C64 | −59.1 (4) | C37—Ca2—C34—C33 | 37.0 (3) |
O3—Ca2—O4—C61 | 38.4 (4) | O4—Ca2—C34—C35 | 170.7 (3) |
C33—Ca2—O4—C61 | 142.2 (4) | O3—Ca2—C34—C35 | −101.5 (3) |
C34—Ca2—O4—C61 | 171.5 (4) | C33—Ca2—C34—C35 | −114.6 (5) |
C53—Ca2—O4—C61 | −94.3 (4) | C53—Ca2—C34—C35 | 78.4 (3) |
C55—Ca2—O4—C61 | −71.2 (4) | C55—Ca2—C34—C35 | 30.1 (3) |
C54—Ca2—O4—C61 | −104.1 (4) | C54—Ca2—C34—C35 | 50.1 (3) |
C56—Ca2—O4—C61 | −48.0 (4) | C56—Ca2—C34—C35 | 45.6 (4) |
C35—Ca2—O4—C61 | 176.9 (3) | C52—Ca2—C34—C35 | 82.7 (3) |
C52—Ca2—O4—C61 | −64.3 (4) | C36—Ca2—C34—C35 | −37.4 (3) |
C36—Ca2—O4—C61 | 142.3 (3) | C37—Ca2—C34—C35 | −77.6 (3) |
C37—Ca2—O4—C61 | 123.2 (4) | C33—C34—C35—C36 | 0.8 (5) |
O1—Ca1—C1—C5 | 32.4 (3) | Ca2—C34—C35—C36 | 69.1 (3) |
O2—Ca1—C1—C5 | 119.2 (3) | C33—C34—C35—C44 | −178.4 (5) |
C23—Ca1—C1—C5 | −84.0 (3) | Ca2—C34—C35—C44 | −110.1 (5) |
C4—Ca1—C1—C5 | −37.8 (3) | C33—C34—C35—Ca2 | −68.2 (3) |
C3—Ca1—C1—C5 | −77.5 (3) | O4—Ca2—C35—C36 | −123.3 (3) |
C24—Ca1—C1—C5 | −116.0 (5) | O3—Ca2—C35—C36 | −5.5 (4) |
C2—Ca1—C1—C5 | −113.6 (4) | C33—Ca2—C35—C36 | −75.8 (3) |
C22—Ca1—C1—C5 | −106.3 (3) | C34—Ca2—C35—C36 | −112.5 (4) |
C21—Ca1—C1—C5 | −138.2 (3) | C53—Ca2—C35—C36 | 145.4 (3) |
C20—Ca1—C1—C5 | −158.6 (3) | C55—Ca2—C35—C36 | 96.6 (3) |
O1—Ca1—C1—C2 | 146.0 (3) | C54—Ca2—C35—C36 | 124.1 (3) |
O2—Ca1—C1—C2 | −127.2 (3) | C56—Ca2—C35—C36 | 100.6 (3) |
C23—Ca1—C1—C2 | 29.6 (4) | C52—Ca2—C35—C36 | 133.0 (3) |
C4—Ca1—C1—C2 | 75.8 (3) | C37—Ca2—C35—C36 | −36.0 (3) |
C3—Ca1—C1—C2 | 36.1 (3) | O4—Ca2—C35—C34 | −10.8 (3) |
C24—Ca1—C1—C2 | −2.4 (7) | O3—Ca2—C35—C34 | 106.9 (3) |
C22—Ca1—C1—C2 | 7.3 (3) | C33—Ca2—C35—C34 | 36.7 (3) |
C5—Ca1—C1—C2 | 113.6 (4) | C53—Ca2—C35—C34 | −102.1 (3) |
C21—Ca1—C1—C2 | −24.6 (3) | C55—Ca2—C35—C34 | −150.9 (3) |
C20—Ca1—C1—C2 | −45.0 (4) | C54—Ca2—C35—C34 | −123.5 (3) |
C5—C1—C2—C3 | 1.4 (5) | C56—Ca2—C35—C34 | −146.9 (3) |
Ca1—C1—C2—C3 | −67.5 (3) | C52—Ca2—C35—C34 | −114.5 (3) |
C5—C1—C2—Ca1 | 68.9 (3) | C36—Ca2—C35—C34 | 112.5 (4) |
O1—Ca1—C2—C3 | 67.5 (3) | C37—Ca2—C35—C34 | 76.4 (3) |
O2—Ca1—C2—C3 | 171.2 (3) | O4—Ca2—C35—C44 | 120.1 (3) |
C23—Ca1—C2—C3 | −43.1 (3) | O3—Ca2—C35—C44 | −122.1 (3) |
C4—Ca1—C2—C3 | 38.1 (3) | C33—Ca2—C35—C44 | 167.6 (4) |
C24—Ca1—C2—C3 | −65.6 (4) | C34—Ca2—C35—C44 | 131.0 (5) |
C1—Ca1—C2—C3 | 115.4 (4) | C53—Ca2—C35—C44 | 28.8 (3) |
C22—Ca1—C2—C3 | −57.6 (3) | C55—Ca2—C35—C44 | −20.0 (3) |
C5—Ca1—C2—C3 | 78.5 (3) | C54—Ca2—C35—C44 | 7.5 (3) |
C21—Ca1—C2—C3 | −87.1 (3) | C56—Ca2—C35—C44 | −16.0 (4) |
C20—Ca1—C2—C3 | −95.6 (3) | C52—Ca2—C35—C44 | 16.4 (4) |
O1—Ca1—C2—C1 | −47.9 (4) | C36—Ca2—C35—C44 | −116.6 (5) |
O2—Ca1—C2—C1 | 55.8 (3) | C37—Ca2—C35—C44 | −152.6 (4) |
C23—Ca1—C2—C1 | −158.5 (3) | C34—C35—C36—C41 | 178.9 (5) |
C4—Ca1—C2—C1 | −77.3 (3) | C44—C35—C36—C41 | −1.8 (7) |
C3—Ca1—C2—C1 | −115.4 (4) | Ca2—C35—C36—C41 | −114.0 (5) |
C24—Ca1—C2—C1 | 179.0 (3) | C34—C35—C36—C37 | 0.0 (5) |
C22—Ca1—C2—C1 | −173.1 (3) | C44—C35—C36—C37 | 179.3 (4) |
C5—Ca1—C2—C1 | −36.9 (3) | Ca2—C35—C36—C37 | 67.1 (3) |
C21—Ca1—C2—C1 | 157.4 (3) | C34—C35—C36—Ca2 | −67.1 (3) |
C20—Ca1—C2—C1 | 149.0 (3) | C44—C35—C36—Ca2 | 112.3 (4) |
C1—C2—C3—C4 | −0.8 (5) | O4—Ca2—C36—C35 | 78.1 (4) |
Ca1—C2—C3—C4 | −68.7 (3) | O3—Ca2—C36—C35 | 175.8 (3) |
C1—C2—C3—C12 | 178.5 (5) | C33—Ca2—C36—C35 | 78.3 (3) |
Ca1—C2—C3—C12 | 110.6 (5) | C34—Ca2—C36—C35 | 37.9 (3) |
C1—C2—C3—Ca1 | 67.9 (3) | C53—Ca2—C36—C35 | −37.7 (3) |
O1—Ca1—C3—C4 | −20.9 (3) | C55—Ca2—C36—C35 | −79.7 (3) |
O2—Ca1—C3—C4 | 99.5 (3) | C54—Ca2—C36—C35 | −49.6 (3) |
C23—Ca1—C3—C4 | −109.3 (3) | C56—Ca2—C36—C35 | −91.6 (3) |
C24—Ca1—C3—C4 | −117.5 (3) | C52—Ca2—C36—C35 | −64.2 (4) |
C2—Ca1—C3—C4 | 111.6 (4) | C37—Ca2—C36—C35 | 116.3 (5) |
C1—Ca1—C3—C4 | 75.4 (3) | O4—Ca2—C36—C41 | −158.4 (4) |
C22—Ca1—C3—C4 | −134.1 (3) | O3—Ca2—C36—C41 | −60.7 (4) |
C5—Ca1—C3—C4 | 36.2 (3) | C33—Ca2—C36—C41 | −158.2 (5) |
C21—Ca1—C3—C4 | −158.2 (3) | C34—Ca2—C36—C41 | 161.5 (5) |
C20—Ca1—C3—C4 | −150.4 (3) | C53—Ca2—C36—C41 | 85.8 (4) |
O1—Ca1—C3—C2 | −132.6 (3) | C55—Ca2—C36—C41 | 43.9 (4) |
O2—Ca1—C3—C2 | −12.1 (4) | C54—Ca2—C36—C41 | 74.0 (4) |
C23—Ca1—C3—C2 | 139.1 (3) | C56—Ca2—C36—C41 | 32.0 (5) |
C4—Ca1—C3—C2 | −111.6 (4) | C35—Ca2—C36—C41 | 123.6 (6) |
C24—Ca1—C3—C2 | 130.9 (3) | C52—Ca2—C36—C41 | 59.3 (5) |
C1—Ca1—C3—C2 | −36.3 (3) | C37—Ca2—C36—C41 | −120.1 (6) |
C22—Ca1—C3—C2 | 114.2 (3) | O4—Ca2—C36—C37 | −38.2 (4) |
C5—Ca1—C3—C2 | −75.4 (3) | O3—Ca2—C36—C37 | 59.5 (3) |
C21—Ca1—C3—C2 | 90.1 (3) | C33—Ca2—C36—C37 | −38.0 (3) |
C20—Ca1—C3—C2 | 98.0 (3) | C34—Ca2—C36—C37 | −78.4 (4) |
O1—Ca1—C3—C12 | 95.0 (4) | C53—Ca2—C36—C37 | −154.0 (3) |
O2—Ca1—C3—C12 | −144.5 (4) | C55—Ca2—C36—C37 | 164.0 (3) |
C23—Ca1—C3—C12 | 6.7 (4) | C54—Ca2—C36—C37 | −165.9 (3) |
C4—Ca1—C3—C12 | 116.0 (5) | C56—Ca2—C36—C37 | 152.1 (3) |
C24—Ca1—C3—C12 | −1.5 (4) | C35—Ca2—C36—C37 | −116.3 (5) |
C2—Ca1—C3—C12 | −132.4 (5) | C52—Ca2—C36—C37 | 179.4 (3) |
C1—Ca1—C3—C12 | −168.7 (4) | C34—C33—C37—C38 | −178.1 (6) |
C22—Ca1—C3—C12 | −18.2 (4) | Ca2—C33—C37—C38 | 112.7 (7) |
C5—Ca1—C3—C12 | 152.2 (4) | C34—C33—C37—C36 | 1.3 (6) |
C21—Ca1—C3—C12 | −42.3 (4) | Ca2—C33—C37—C36 | −68.0 (3) |
C20—Ca1—C3—C12 | −34.4 (4) | C34—C33—C37—Ca2 | 69.3 (4) |
C2—C3—C4—C9 | 177.6 (4) | C35—C36—C37—C38 | 178.8 (4) |
C12—C3—C4—C9 | −1.8 (7) | C41—C36—C37—C38 | −0.2 (7) |
Ca1—C3—C4—C9 | 108.5 (4) | Ca2—C36—C37—C38 | −114.5 (4) |
C2—C3—C4—C5 | 0.0 (5) | C35—C36—C37—C33 | −0.8 (5) |
C12—C3—C4—C5 | −179.5 (4) | C41—C36—C37—C33 | −179.7 (4) |
Ca1—C3—C4—C5 | −69.2 (3) | Ca2—C36—C37—C33 | 66.0 (3) |
C2—C3—C4—Ca1 | 69.2 (3) | C35—C36—C37—Ca2 | −66.7 (3) |
C12—C3—C4—Ca1 | −110.3 (4) | C41—C36—C37—Ca2 | 114.3 (5) |
O1—Ca1—C4—C3 | 161.8 (3) | O4—Ca2—C37—C38 | −97.1 (5) |
O2—Ca1—C4—C3 | −110.4 (3) | O3—Ca2—C37—C38 | −11.1 (5) |
C23—Ca1—C4—C3 | 70.5 (3) | C33—Ca2—C37—C38 | −136.9 (7) |
C24—Ca1—C4—C3 | 78.7 (3) | C34—Ca2—C37—C38 | −173.9 (6) |
C2—Ca1—C4—C3 | −38.2 (3) | C53—Ca2—C37—C38 | 148.7 (4) |
C1—Ca1—C4—C3 | −78.5 (3) | C55—Ca2—C37—C38 | 93.7 (5) |
C22—Ca1—C4—C3 | 41.0 (3) | C54—Ca2—C37—C38 | 126.6 (5) |
C5—Ca1—C4—C3 | −115.7 (4) | C56—Ca2—C37—C38 | 70.7 (6) |
C21—Ca1—C4—C3 | 23.6 (3) | C35—Ca2—C37—C38 | 146.5 (6) |
C20—Ca1—C4—C3 | 42.7 (4) | C52—Ca2—C37—C38 | 109.8 (7) |
O1—Ca1—C4—C9 | 38.0 (3) | C36—Ca2—C37—C38 | 111.2 (6) |
O2—Ca1—C4—C9 | 125.7 (3) | O4—Ca2—C37—C33 | 39.8 (4) |
C23—Ca1—C4—C9 | −53.3 (4) | O3—Ca2—C37—C33 | 125.8 (4) |
C3—Ca1—C4—C9 | −123.8 (5) | C34—Ca2—C37—C33 | −37.0 (3) |
C24—Ca1—C4—C9 | −45.1 (4) | C53—Ca2—C37—C33 | −74.4 (4) |
C2—Ca1—C4—C9 | −162.0 (4) | C55—Ca2—C37—C33 | −129.4 (4) |
C1—Ca1—C4—C9 | 157.7 (4) | C54—Ca2—C37—C33 | −96.5 (4) |
C22—Ca1—C4—C9 | −82.8 (3) | C56—Ca2—C37—C33 | −152.4 (3) |
C5—Ca1—C4—C9 | 120.5 (5) | C35—Ca2—C37—C33 | −76.6 (4) |
C21—Ca1—C4—C9 | −100.3 (4) | C52—Ca2—C37—C33 | −113.3 (6) |
C20—Ca1—C4—C9 | −81.1 (4) | C36—Ca2—C37—C33 | −111.9 (5) |
O1—Ca1—C4—C5 | −82.5 (3) | O4—Ca2—C37—C36 | 151.7 (3) |
O2—Ca1—C4—C5 | 5.3 (3) | O3—Ca2—C37—C36 | −122.4 (3) |
C23—Ca1—C4—C5 | −173.7 (3) | C33—Ca2—C37—C36 | 111.9 (5) |
C3—Ca1—C4—C5 | 115.7 (4) | C34—Ca2—C37—C36 | 74.9 (3) |
C24—Ca1—C4—C5 | −165.6 (3) | C53—Ca2—C37—C36 | 37.5 (4) |
C2—Ca1—C4—C5 | 77.5 (3) | C55—Ca2—C37—C36 | −17.6 (4) |
C1—Ca1—C4—C5 | 37.2 (3) | C54—Ca2—C37—C36 | 15.4 (4) |
C22—Ca1—C4—C5 | 156.8 (3) | C56—Ca2—C37—C36 | −40.5 (4) |
C21—Ca1—C4—C5 | 139.3 (3) | C35—Ca2—C37—C36 | 35.3 (3) |
C20—Ca1—C4—C5 | 158.4 (3) | C52—Ca2—C37—C36 | −1.4 (8) |
C2—C1—C5—C6 | 179.3 (5) | C33—C37—C38—C39 | 179.0 (6) |
Ca1—C1—C5—C6 | −112.6 (6) | C36—C37—C38—C39 | −0.2 (8) |
C2—C1—C5—C4 | −1.4 (5) | Ca2—C37—C38—C39 | −86.1 (6) |
Ca1—C1—C5—C4 | 66.6 (3) | C37—C38—C39—C40 | 1.3 (9) |
C2—C1—C5—Ca1 | −68.0 (3) | C38—C39—C40—C41 | −1.9 (9) |
C3—C4—C5—C1 | 0.9 (5) | C39—C40—C41—C36 | 1.4 (8) |
C9—C4—C5—C1 | −176.9 (4) | C39—C40—C41—C42 | −175.4 (5) |
Ca1—C4—C5—C1 | −67.5 (3) | C35—C36—C41—C40 | −179.1 (5) |
C3—C4—C5—C6 | −179.7 (4) | C37—C36—C41—C40 | −0.4 (7) |
C9—C4—C5—C6 | 2.6 (6) | Ca2—C36—C41—C40 | 89.7 (5) |
Ca1—C4—C5—C6 | 111.9 (4) | C35—C36—C41—C42 | −2.0 (7) |
C3—C4—C5—Ca1 | 68.4 (3) | C37—C36—C41—C42 | 176.8 (4) |
C9—C4—C5—Ca1 | −109.4 (4) | Ca2—C36—C41—C42 | −93.1 (5) |
O1—Ca1—C5—C1 | −150.3 (3) | C40—C41—C42—C43 | 178.0 (5) |
O2—Ca1—C5—C1 | −63.1 (3) | C36—C41—C42—C43 | 1.2 (7) |
C23—Ca1—C5—C1 | 120.5 (3) | C41—C42—C43—C44 | 3.5 (8) |
C4—Ca1—C5—C1 | 112.9 (4) | C36—C35—C44—C43 | 5.5 (6) |
C3—Ca1—C5—C1 | 77.0 (3) | C34—C35—C44—C43 | −175.3 (5) |
C24—Ca1—C5—C1 | 139.8 (4) | Ca2—C35—C44—C43 | 93.6 (4) |
C2—Ca1—C5—C1 | 37.3 (3) | C36—C35—C44—C45 | −118.4 (5) |
C22—Ca1—C5—C1 | 86.8 (3) | C34—C35—C44—C45 | 60.7 (7) |
C21—Ca1—C5—C1 | 57.1 (3) | Ca2—C35—C44—C45 | −30.3 (5) |
C20—Ca1—C5—C1 | 55.9 (6) | C42—C43—C44—C35 | −6.7 (7) |
O1—Ca1—C5—C6 | −15.7 (4) | C42—C43—C44—C45 | 119.5 (6) |
O2—Ca1—C5—C6 | 71.4 (4) | C35—C44—C45—C46 | −78.1 (5) |
C23—Ca1—C5—C6 | −104.9 (4) | C43—C44—C45—C46 | 157.5 (4) |
C4—Ca1—C5—C6 | −112.5 (5) | C35—C44—C45—C54 | 46.0 (6) |
C3—Ca1—C5—C6 | −148.4 (5) | C43—C44—C45—C54 | −78.4 (6) |
C24—Ca1—C5—C6 | −85.6 (5) | C54—C45—C46—C47 | −0.2 (8) |
C2—Ca1—C5—C6 | 171.9 (5) | C44—C45—C46—C47 | 125.8 (6) |
C1—Ca1—C5—C6 | 134.6 (5) | C45—C46—C47—C48 | 0.9 (9) |
C22—Ca1—C5—C6 | −138.6 (4) | C46—C47—C48—C49 | 178.5 (5) |
C21—Ca1—C5—C6 | −168.3 (4) | C46—C47—C48—C53 | −0.9 (7) |
C20—Ca1—C5—C6 | −169.5 (5) | C53—C48—C49—C50 | −1.4 (7) |
O1—Ca1—C5—C4 | 96.8 (3) | C47—C48—C49—C50 | 179.3 (5) |
O2—Ca1—C5—C4 | −176.0 (3) | C48—C49—C50—C51 | 0.4 (8) |
C23—Ca1—C5—C4 | 7.6 (3) | C49—C50—C51—C52 | 0.2 (8) |
C3—Ca1—C5—C4 | −35.9 (3) | C50—C51—C52—C56 | −179.1 (5) |
C24—Ca1—C5—C4 | 26.9 (5) | C50—C51—C52—C53 | 0.3 (7) |
C2—Ca1—C5—C4 | −75.5 (3) | C50—C51—C52—Ca2 | −83.8 (5) |
C1—Ca1—C5—C4 | −112.9 (4) | O4—Ca2—C52—C56 | 149.3 (3) |
C22—Ca1—C5—C4 | −26.0 (3) | O3—Ca2—C52—C56 | 62.5 (3) |
C21—Ca1—C5—C4 | −55.8 (3) | C33—Ca2—C52—C56 | −139.4 (4) |
C20—Ca1—C5—C4 | −56.9 (6) | C34—Ca2—C52—C56 | −120.7 (3) |
C1—C5—C6—C7 | 179.1 (6) | C53—Ca2—C52—C56 | −112.2 (4) |
C4—C5—C6—C7 | −0.1 (7) | C55—Ca2—C52—C56 | −37.0 (3) |
Ca1—C5—C6—C7 | 83.8 (5) | C54—Ca2—C52—C56 | −76.5 (3) |
C5—C6—C7—C8 | −1.8 (8) | C35—Ca2—C52—C56 | −87.1 (3) |
C6—C7—C8—C9 | 1.4 (8) | C36—Ca2—C52—C56 | −57.3 (3) |
C7—C8—C9—C4 | 1.0 (7) | C37—Ca2—C52—C56 | −56.3 (7) |
C7—C8—C9—C10 | −178.6 (5) | O4—Ca2—C52—C51 | 14.0 (4) |
C3—C4—C9—C8 | 179.6 (4) | O3—Ca2—C52—C51 | −72.8 (4) |
C5—C4—C9—C8 | −3.0 (7) | C33—Ca2—C52—C51 | 85.3 (5) |
Ca1—C4—C9—C8 | −91.7 (4) | C34—Ca2—C52—C51 | 104.0 (4) |
C3—C4—C9—C10 | −0.8 (7) | C53—Ca2—C52—C51 | 112.5 (5) |
C5—C4—C9—C10 | 176.6 (4) | C55—Ca2—C52—C51 | −172.3 (5) |
Ca1—C4—C9—C10 | 87.9 (4) | C54—Ca2—C52—C51 | 148.2 (5) |
C8—C9—C10—C11 | −179.6 (5) | C56—Ca2—C52—C51 | −135.3 (5) |
C4—C9—C10—C11 | 0.8 (7) | C35—Ca2—C52—C51 | 137.6 (4) |
C9—C10—C11—C12 | 1.9 (9) | C36—Ca2—C52—C51 | 167.4 (3) |
C10—C11—C12—C3 | −4.1 (8) | C37—Ca2—C52—C51 | 168.4 (6) |
C10—C11—C12—C13 | −129.0 (6) | O4—Ca2—C52—C53 | −98.6 (3) |
C4—C3—C12—C11 | 3.8 (6) | O3—Ca2—C52—C53 | 174.6 (3) |
C2—C3—C12—C11 | −175.4 (5) | C33—Ca2—C52—C53 | −27.3 (5) |
Ca1—C3—C12—C11 | −82.0 (5) | C34—Ca2—C52—C53 | −8.5 (3) |
C4—C3—C12—C13 | 127.3 (5) | C55—Ca2—C52—C53 | 75.2 (3) |
C2—C3—C12—C13 | −52.0 (7) | C54—Ca2—C52—C53 | 35.7 (3) |
Ca1—C3—C12—C13 | 41.4 (5) | C56—Ca2—C52—C53 | 112.2 (4) |
C11—C12—C13—C22 | 75.7 (6) | C35—Ca2—C52—C53 | 25.1 (3) |
C3—C12—C13—C22 | −48.2 (6) | C36—Ca2—C52—C53 | 54.9 (4) |
C11—C12—C13—C14 | −160.8 (4) | C37—Ca2—C52—C53 | 55.8 (7) |
C3—C12—C13—C14 | 75.4 (5) | C49—C48—C53—C54 | −179.2 (4) |
C22—C13—C14—C15 | 4.4 (6) | C47—C48—C53—C54 | 0.3 (7) |
C12—C13—C14—C15 | −120.3 (5) | C49—C48—C53—C52 | 1.9 (7) |
C13—C14—C15—C16 | −1.6 (8) | C47—C48—C53—C52 | −178.7 (4) |
C14—C15—C16—C17 | −178.3 (5) | C49—C48—C53—Ca2 | 91.0 (5) |
C14—C15—C16—C21 | −1.6 (7) | C47—C48—C53—Ca2 | −89.6 (4) |
C21—C16—C17—C18 | 0.0 (8) | C56—C52—C53—C54 | −0.9 (5) |
C15—C16—C17—C18 | 176.6 (5) | C51—C52—C53—C54 | 179.6 (4) |
C16—C17—C18—C19 | −0.3 (10) | Ca2—C52—C53—C54 | −68.5 (3) |
C17—C18—C19—C20 | 0.4 (9) | C56—C52—C53—C48 | 178.2 (4) |
C18—C19—C20—C21 | −0.3 (8) | C51—C52—C53—C48 | −1.3 (7) |
C18—C19—C20—C24 | −179.6 (6) | Ca2—C52—C53—C48 | 110.6 (4) |
C18—C19—C20—Ca1 | 86.6 (6) | C56—C52—C53—Ca2 | 67.6 (3) |
O1—Ca1—C20—C21 | −150.5 (3) | C51—C52—C53—Ca2 | −112.0 (4) |
O2—Ca1—C20—C21 | 122.8 (3) | O4—Ca2—C53—C54 | −162.9 (3) |
C23—Ca1—C20—C21 | −75.5 (3) | O3—Ca2—C53—C54 | 108.5 (3) |
C4—Ca1—C20—C21 | −37.6 (4) | C33—Ca2—C53—C54 | −79.2 (3) |
C3—Ca1—C20—C21 | −15.9 (4) | C34—Ca2—C53—C54 | −71.4 (3) |
C24—Ca1—C20—C21 | −113.6 (5) | C55—Ca2—C53—C54 | 37.8 (3) |
C2—Ca1—C20—C21 | 17.2 (4) | C56—Ca2—C53—C54 | 77.9 (3) |
C1—Ca1—C20—C21 | 40.2 (4) | C35—Ca2—C53—C54 | −41.9 (3) |
C22—Ca1—C20—C21 | −35.4 (3) | C52—Ca2—C53—C54 | 115.6 (4) |
C5—Ca1—C20—C21 | 1.7 (7) | C36—Ca2—C53—C54 | −24.2 (3) |
O1—Ca1—C20—C24 | −36.9 (4) | C37—Ca2—C53—C54 | −43.5 (4) |
O2—Ca1—C20—C24 | −123.5 (4) | O4—Ca2—C53—C48 | −38.4 (4) |
C23—Ca1—C20—C24 | 38.2 (3) | O3—Ca2—C53—C48 | −127.0 (3) |
C4—Ca1—C20—C24 | 76.0 (4) | C33—Ca2—C53—C48 | 45.3 (4) |
C3—Ca1—C20—C24 | 97.8 (4) | C34—Ca2—C53—C48 | 53.1 (4) |
C2—Ca1—C20—C24 | 130.8 (4) | C55—Ca2—C53—C48 | 162.3 (4) |
C1—Ca1—C20—C24 | 153.8 (3) | C54—Ca2—C53—C48 | 124.5 (5) |
C22—Ca1—C20—C24 | 78.2 (4) | C56—Ca2—C53—C48 | −157.6 (4) |
C5—Ca1—C20—C24 | 115.3 (6) | C35—Ca2—C53—C48 | 82.6 (4) |
C21—Ca1—C20—C24 | 113.6 (5) | C52—Ca2—C53—C48 | −119.8 (5) |
O1—Ca1—C20—C19 | 95.5 (5) | C36—Ca2—C53—C48 | 100.4 (4) |
O2—Ca1—C20—C19 | 8.9 (5) | C37—Ca2—C53—C48 | 81.0 (4) |
C23—Ca1—C20—C19 | 170.6 (6) | O4—Ca2—C53—C52 | 81.4 (3) |
C4—Ca1—C20—C19 | −151.6 (4) | O3—Ca2—C53—C52 | −7.1 (4) |
C3—Ca1—C20—C19 | −129.8 (5) | C33—Ca2—C53—C52 | 165.1 (3) |
C24—Ca1—C20—C19 | 132.5 (7) | C34—Ca2—C53—C52 | 173.0 (3) |
C2—Ca1—C20—C19 | −96.8 (5) | C55—Ca2—C53—C52 | −77.8 (3) |
C1—Ca1—C20—C19 | −73.8 (6) | C54—Ca2—C53—C52 | −115.6 (4) |
C22—Ca1—C20—C19 | −149.4 (6) | C56—Ca2—C53—C52 | −37.7 (3) |
C5—Ca1—C20—C19 | −112.2 (6) | C35—Ca2—C53—C52 | −157.5 (3) |
C21—Ca1—C20—C19 | −113.9 (6) | C36—Ca2—C53—C52 | −139.8 (3) |
C17—C16—C21—C22 | 178.7 (5) | C37—Ca2—C53—C52 | −159.2 (3) |
C15—C16—C21—C22 | 1.7 (7) | C48—C53—C54—C55 | −178.5 (5) |
C17—C16—C21—C20 | 0.2 (7) | C52—C53—C54—C55 | 0.5 (5) |
C15—C16—C21—C20 | −176.8 (5) | Ca2—C53—C54—C55 | −68.6 (3) |
C17—C16—C21—Ca1 | −90.6 (5) | C48—C53—C54—C45 | 0.4 (7) |
C15—C16—C21—Ca1 | 92.4 (5) | C52—C53—C54—C45 | 179.4 (4) |
C24—C20—C21—C16 | 179.5 (5) | Ca2—C53—C54—C45 | 110.4 (4) |
C19—C20—C21—C16 | 0.0 (7) | C48—C53—C54—Ca2 | −110.0 (5) |
Ca1—C20—C21—C16 | −114.0 (5) | C52—C53—C54—Ca2 | 69.1 (3) |
C24—C20—C21—C22 | 0.8 (6) | C46—C45—C54—C53 | −0.4 (6) |
C19—C20—C21—C22 | −178.7 (4) | C44—C45—C54—C53 | −125.2 (5) |
Ca1—C20—C21—C22 | 67.3 (3) | C46—C45—C54—C55 | 178.1 (5) |
C24—C20—C21—Ca1 | −66.5 (4) | C44—C45—C54—C55 | 53.4 (8) |
C19—C20—C21—Ca1 | 114.0 (5) | C46—C45—C54—Ca2 | 85.9 (4) |
O1—Ca1—C21—C16 | 161.1 (4) | C44—C45—C54—Ca2 | −38.9 (6) |
O2—Ca1—C21—C16 | 62.0 (4) | O4—Ca2—C54—C53 | 19.9 (3) |
C23—Ca1—C21—C16 | −160.9 (5) | O3—Ca2—C54—C53 | −101.0 (3) |
C4—Ca1—C21—C16 | −85.0 (4) | C33—Ca2—C54—C53 | 116.6 (3) |
C3—Ca1—C21—C16 | −73.4 (4) | C34—Ca2—C54—C53 | 108.3 (3) |
C24—Ca1—C21—C16 | 158.4 (5) | C55—Ca2—C54—C53 | −112.4 (4) |
C2—Ca1—C21—C16 | −43.1 (4) | C56—Ca2—C54—C53 | −75.9 (3) |
C1—Ca1—C21—C16 | −30.9 (4) | C35—Ca2—C54—C53 | 133.2 (3) |
C22—Ca1—C21—C16 | −122.4 (6) | C52—Ca2—C54—C53 | −36.4 (3) |
C5—Ca1—C21—C16 | −58.1 (5) | C36—Ca2—C54—C53 | 157.6 (3) |
C20—Ca1—C21—C16 | 121.2 (5) | C37—Ca2—C54—C53 | 149.8 (3) |
O1—Ca1—C21—C22 | −76.5 (4) | O4—Ca2—C54—C55 | 132.3 (3) |
O2—Ca1—C21—C22 | −175.6 (3) | O3—Ca2—C54—C55 | 11.3 (4) |
C23—Ca1—C21—C22 | −38.5 (3) | C33—Ca2—C54—C55 | −131.0 (3) |
C4—Ca1—C21—C22 | 37.4 (3) | C34—Ca2—C54—C55 | −139.4 (3) |
C3—Ca1—C21—C22 | 49.0 (3) | C53—Ca2—C54—C55 | 112.4 (4) |
C24—Ca1—C21—C22 | −79.1 (3) | C56—Ca2—C54—C55 | 36.4 (3) |
C2—Ca1—C21—C22 | 79.3 (3) | C35—Ca2—C54—C55 | −114.5 (3) |
C1—Ca1—C21—C22 | 91.5 (3) | C52—Ca2—C54—C55 | 76.0 (3) |
C5—Ca1—C21—C22 | 64.3 (4) | C36—Ca2—C54—C55 | −90.1 (3) |
C20—Ca1—C21—C22 | −116.4 (5) | C37—Ca2—C54—C55 | −97.8 (3) |
O1—Ca1—C21—C20 | 39.9 (4) | O4—Ca2—C54—C45 | −96.8 (4) |
O2—Ca1—C21—C20 | −59.2 (3) | O3—Ca2—C54—C45 | 142.3 (4) |
C23—Ca1—C21—C20 | 77.9 (4) | C33—Ca2—C54—C45 | −0.1 (4) |
C4—Ca1—C21—C20 | 153.8 (3) | C34—Ca2—C54—C45 | −8.4 (4) |
C3—Ca1—C21—C20 | 165.4 (3) | C53—Ca2—C54—C45 | −116.7 (5) |
C24—Ca1—C21—C20 | 37.2 (3) | C55—Ca2—C54—C45 | 130.9 (5) |
C2—Ca1—C21—C20 | −164.3 (3) | C56—Ca2—C54—C45 | 167.4 (5) |
C1—Ca1—C21—C20 | −152.1 (3) | C35—Ca2—C54—C45 | 16.5 (4) |
C22—Ca1—C21—C20 | 116.4 (5) | C52—Ca2—C54—C45 | −153.1 (5) |
C5—Ca1—C21—C20 | −179.3 (3) | C36—Ca2—C54—C45 | 40.9 (4) |
C16—C21—C22—C23 | −179.7 (5) | C37—Ca2—C54—C45 | 33.1 (4) |
C20—C21—C22—C23 | −1.1 (5) | C53—C54—C55—C56 | 0.1 (5) |
Ca1—C21—C22—C23 | 66.6 (3) | C45—C54—C55—C56 | −178.6 (5) |
C16—C21—C22—C13 | 1.5 (7) | Ca2—C54—C55—C56 | −68.5 (3) |
C20—C21—C22—C13 | −179.8 (4) | C53—C54—C55—Ca2 | 68.5 (3) |
Ca1—C21—C22—C13 | −112.1 (4) | C45—C54—C55—Ca2 | −110.2 (5) |
C16—C21—C22—Ca1 | 113.6 (5) | O4—Ca2—C55—C54 | −68.9 (4) |
C20—C21—C22—Ca1 | −67.7 (4) | O3—Ca2—C55—C54 | −171.7 (3) |
C14—C13—C22—C21 | −4.2 (6) | C33—Ca2—C55—C54 | 65.2 (4) |
C12—C13—C22—C21 | 119.1 (5) | C34—Ca2—C55—C54 | 42.7 (3) |
C14—C13—C22—C23 | 177.5 (5) | C53—Ca2—C55—C54 | −37.6 (3) |
C12—C13—C22—C23 | −59.2 (7) | C56—Ca2—C55—C54 | −115.0 (5) |
C14—C13—C22—Ca1 | −92.2 (4) | C35—Ca2—C55—C54 | 57.5 (3) |
C12—C13—C22—Ca1 | 31.1 (6) | C52—Ca2—C55—C54 | −78.0 (3) |
O1—Ca1—C22—C21 | 124.5 (3) | C36—Ca2—C55—C54 | 87.2 (3) |
O2—Ca1—C22—C21 | 5.8 (4) | C37—Ca2—C55—C54 | 96.0 (3) |
C23—Ca1—C22—C21 | 111.5 (4) | O4—Ca2—C55—C56 | 46.1 (4) |
C4—Ca1—C22—C21 | −145.9 (3) | O3—Ca2—C55—C56 | −56.7 (3) |
C3—Ca1—C22—C21 | −124.7 (3) | C33—Ca2—C55—C56 | −179.8 (3) |
C24—Ca1—C22—C21 | 75.1 (3) | C34—Ca2—C55—C56 | 157.7 (3) |
C2—Ca1—C22—C21 | −97.0 (3) | C53—Ca2—C55—C56 | 77.4 (3) |
C1—Ca1—C22—C21 | −100.8 (3) | C54—Ca2—C55—C56 | 115.0 (5) |
C5—Ca1—C22—C21 | −133.0 (3) | C35—Ca2—C55—C56 | 172.5 (3) |
C20—Ca1—C22—C21 | 35.6 (3) | C52—Ca2—C55—C56 | 37.0 (3) |
O1—Ca1—C22—C23 | 13.0 (4) | C36—Ca2—C55—C56 | −157.8 (3) |
O2—Ca1—C22—C23 | −105.7 (3) | C37—Ca2—C55—C56 | −149.0 (3) |
C4—Ca1—C22—C23 | 102.6 (3) | C54—C55—C56—C52 | −0.6 (5) |
C3—Ca1—C22—C23 | 123.8 (3) | Ca2—C55—C56—C52 | −68.9 (3) |
C24—Ca1—C22—C23 | −36.4 (3) | C54—C55—C56—Ca2 | 68.3 (3) |
C2—Ca1—C22—C23 | 151.5 (3) | C51—C52—C56—C55 | −179.7 (5) |
C1—Ca1—C22—C23 | 147.7 (3) | C53—C52—C56—C55 | 0.9 (5) |
C5—Ca1—C22—C23 | 115.5 (3) | Ca2—C52—C56—C55 | 67.9 (3) |
C21—Ca1—C22—C23 | −111.5 (4) | C51—C52—C56—Ca2 | 112.4 (6) |
C20—Ca1—C22—C23 | −75.9 (3) | C53—C52—C56—Ca2 | −67.0 (3) |
O1—Ca1—C22—C13 | −118.4 (4) | O4—Ca2—C56—C55 | −147.6 (3) |
O2—Ca1—C22—C13 | 123.0 (4) | O3—Ca2—C56—C55 | 126.2 (3) |
C23—Ca1—C22—C13 | −131.3 (6) | C33—Ca2—C56—C55 | 0.4 (7) |
C4—Ca1—C22—C13 | −28.7 (4) | C34—Ca2—C56—C55 | −30.5 (4) |
C3—Ca1—C22—C13 | −7.5 (4) | C53—Ca2—C56—C55 | −75.8 (3) |
C24—Ca1—C22—C13 | −167.7 (5) | C54—Ca2—C56—C55 | −36.3 (3) |
C2—Ca1—C22—C13 | 20.1 (4) | C35—Ca2—C56—C55 | −7.9 (3) |
C1—Ca1—C22—C13 | 16.4 (4) | C52—Ca2—C56—C55 | −113.9 (4) |
C5—Ca1—C22—C13 | −15.8 (4) | C36—Ca2—C56—C55 | 24.1 (3) |
C21—Ca1—C22—C13 | 117.2 (5) | C37—Ca2—C56—C55 | 45.0 (4) |
C20—Ca1—C22—C13 | 152.8 (5) | O4—Ca2—C56—C52 | −33.8 (3) |
C21—C22—C23—C24 | 0.9 (5) | O3—Ca2—C56—C52 | −119.9 (3) |
C13—C22—C23—C24 | 179.4 (4) | C33—Ca2—C56—C52 | 114.3 (5) |
Ca1—C22—C23—C24 | 69.9 (3) | C34—Ca2—C56—C52 | 83.4 (3) |
C21—C22—C23—Ca1 | −69.0 (3) | C53—Ca2—C56—C52 | 38.1 (3) |
C13—C22—C23—Ca1 | 109.5 (5) | C55—Ca2—C56—C52 | 113.9 (4) |
O1—Ca1—C23—C24 | 75.8 (3) | C54—Ca2—C56—C52 | 77.6 (3) |
O2—Ca1—C23—C24 | −12.5 (4) | C35—Ca2—C56—C52 | 106.0 (3) |
C4—Ca1—C23—C24 | 166.6 (3) | C36—Ca2—C56—C52 | 138.0 (3) |
C3—Ca1—C23—C24 | −165.0 (3) | C37—Ca2—C56—C52 | 158.9 (3) |
C2—Ca1—C23—C24 | −144.9 (3) | C60—O3—C57—C58 | 23.0 (7) |
C1—Ca1—C23—C24 | −160.0 (3) | Ca2—O3—C57—C58 | −150.7 (4) |
C22—Ca1—C23—C24 | −115.3 (5) | O3—C57—C58—C59 | −6.9 (8) |
C5—Ca1—C23—C24 | 162.7 (3) | C57—C58—C59—C60 | −11.1 (7) |
C21—Ca1—C23—C24 | −77.5 (4) | C57—O3—C60—C59 | −30.3 (6) |
C20—Ca1—C23—C24 | −37.7 (3) | Ca2—O3—C60—C59 | 142.9 (4) |
O1—Ca1—C23—C22 | −168.9 (3) | C58—C59—C60—O3 | 25.5 (6) |
O2—Ca1—C23—C22 | 102.8 (3) | C64—O4—C61—C62 | 41.2 (5) |
C4—Ca1—C23—C22 | −78.2 (3) | Ca2—O4—C61—C62 | −140.6 (4) |
C3—Ca1—C23—C22 | −49.8 (3) | O4—C61—C62—C63 | −37.0 (5) |
C24—Ca1—C23—C22 | 115.3 (5) | C61—C62—C63—C64 | 19.1 (5) |
C2—Ca1—C23—C22 | −29.6 (3) | C61—O4—C64—C63 | −28.5 (5) |
C1—Ca1—C23—C22 | −44.7 (4) | Ca2—O4—C64—C63 | 153.4 (3) |
C5—Ca1—C23—C22 | −82.0 (3) | C62—C63—C64—O4 | 5.1 (6) |
Experimental details
Crystal data | |
Chemical formula | [Ca(C24H12)(C4H8O)2] |
Mr | 488.66 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 203 |
a, b, c (Å) | 16.1497 (14), 8.6805 (7), 35.047 (3) |
V (Å3) | 4913.2 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.24 × 0.14 × 0.05 |
Data collection | |
Diffractometer | Siemens SMART 1K diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.935, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36582, 8481, 5906 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.128, 1.01 |
No. of reflections | 8481 |
No. of parameters | 631 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.78, −0.22 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.11 (5) |
Computer programs: SMART (Bruker, 1998), SMART, SAINT-Plus (Bruker, 1999), XS in SHELXTL (Sheldrick, 1998), XL in SHELXTL, XP in SHELXTL, XCIF in SHELXTL.
(2) | (3) | (4) | (5) | (6) | |
Ca-Cp(cent)Å | 2.39 | 2.40 | 2.35 | 2.45 | 2.38 |
Ca-OÅ | - | 2.38 | 2.42 | 2.34 | 2.39 |
Cp-Ca-Cp° | 119.1 | 120.4 | 119.9 | 118.6 | 121.3 |
Dihedral° | 61.1 | 61.3 | 63.0 | 66.2 | 59.6 |
Note: Average values given. |
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We have continued our studies on the synthesis of ansa-calcocenes as useful reagents for ligand transfer reactions, and have synthesized and structurally characterized the title rac-(acenaphthylenide)2calcium(THF)2 complex, (I). This complex is synthesized by coupling the neutral ligand with HgCl2 activated calcium in the presence of THF. A similar synthesis was recently described in the literature (Fedushkin, Petovskaya et al., 2001).
Complex (I) crystallizes in the orthorhombic system Pca21 with two independent molecules in the asymmetric unit. The coupling induced by the actived calcium exclusively yields the C2-symmetric rac-ansa complex, and both enantiomers are present and are shown in Fig. 1. The calcium center is η5-bonded to both cyclopentadienyl (Cp) moieties of the biacenaphthylenide framework and η1 to both tetrahydrofuran molecules, resulting in a distorted pseudo-tetrahedral enviroment and a four-coordinate calcium. Most of the geometrical features of both enantiomers (identified by the central Ca atom) are essentially identical: Ca—Cp(centroid) [Ca1: 2.347 (4) and 2.446 (4) Å; Ca2: 2.446 (4) and 2.438 (4) Å]; Ca—O distances [Ca1: 2.346 (4) and 2.354 (4) Å; Ca2: 2.357 (4) and 2.351 (4) Å]; Cp—Ca—Cp(centroid) angles [Ca1: 119.1 (2); Ca2: 118.8 (2)]; O—Ca—O angles [Ca1: 87.93 (13); Ca2: 87.39 (14)]. The dihedral angles between the acene rings in (I) are 62.49 (7) (Ca1) and 61.50 (7)° (Ca2).
Complex (I) displays many similarities with the few structurally characterized ansa-calcocenes in general. These main structural features are given in Table 1 for the following complexes: Me4C2(η5-C5H4)2Ca{(CH3)3CN(CH)2NC(CH3)3}, (II) (Reickhoff et al., 1993), cis- and trans-Ph2C2H2(η5-C5H4)2Ca(thf)2, (III) and (IV) (Matare et al., 1998; Kane et al., 1997), trans-Ph2C2H2-rac-(η5-4,7-Me2C9H4)2Ca(thf)2, (V) (Shapiro et al., 1999), and trans-Ph2(CH3)2C2(η5-C5H4)2Ca(DME), (VI) (Twamley et al., 2001).
The fused acene unit has also been observed in the lanthanide complexes rac-(C12H6)2Ln(C4H8O)2 (Ln = Yb, Sm; Fedushkin, Dechert & Schumann, 2001). These complexes are isostructural with (I) and show similar geometry [acene dihedral angles: 63.9 and 62.7° (Yb); 63.6° (Sm)]. The fusion C—C bond distance in the lanthanide complexes [1.556 (4) and 1.573 (4) Å (Yb), and 1.568 (3) Å (Sm)] is similar to that in (I) [1.586 (7) and 1.559 (7) Å].