Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011844/om6097sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011844/om6097Isup2.hkl |
CCDC reference: 193755
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.090
- Data-to-parameter ratio = 11.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.50 From the CIF: _reflns_number_total 6629 Count of symmetry unique reflns 6654 Completeness (_total/calc) 99.62% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no 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.
Data collection: COLLECT (Nonius 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare, et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C21H22O10 | F(000) = 912 |
Mr = 434.39 | Dx = 1.380 Mg m−3 |
Monoclinic, P21 | Melting point: 492-495K K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 7.646 (2) Å | Cell parameters from 6013 reflections |
b = 11.633 (2) Å | θ = 2.5–30.5° |
c = 23.709 (4) Å | µ = 0.11 mm−1 |
β = 97.385 (6)° | T = 120 K |
V = 2091.3 (7) Å3 | Fragment, colorless |
Z = 4 | 0.47 × 0.35 × 0.25 mm |
KappaCCD (with Oxford Cryosystems Cryostream cooler) diffractometer | 5688 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 30.5°, θmin = 2.6° |
ω scans with κ offsets | h = −10→10 |
23672 measured reflections | k = −16→16 |
6629 independent reflections | l = −33→33 |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0326P)2 + 0.6091P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
6629 reflections | Δρmax = 0.26 e Å−3 |
568 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0074 (11) |
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 | ||
O1 | 0.28331 (18) | 0.00036 (13) | 0.56993 (6) | 0.0204 (3) | |
O2 | 0.4839 (2) | −0.13872 (14) | 0.58788 (7) | 0.0301 (4) | |
O3 | −0.0298 (2) | 0.51331 (16) | 0.64556 (7) | 0.0310 (4) | |
O4 | 0.2757 (2) | 0.42377 (13) | 0.69863 (6) | 0.0238 (3) | |
O5 | 0.5202 (2) | 0.38905 (14) | 0.60432 (8) | 0.0297 (4) | |
O6 | 0.3654 (2) | 0.55119 (13) | 0.58477 (7) | 0.0255 (3) | |
O7 | 0.1026 (2) | 0.41375 (14) | 0.51292 (6) | 0.0264 (3) | |
O8 | 0.32393 (19) | 0.14307 (13) | 0.72733 (6) | 0.0210 (3) | |
O9 | 0.4951 (3) | 0.23224 (19) | 0.79823 (7) | 0.0481 (5) | |
O10 | 0.4073 (2) | 0.06612 (18) | 0.87590 (6) | 0.0356 (4) | |
C1 | 0.0588 (3) | 0.46590 (19) | 0.61429 (9) | 0.0218 (4) | |
C2 | −0.0085 (3) | 0.4581 (2) | 0.55216 (9) | 0.0244 (4) | |
H2 | −0.0881 | 0.5223 | 0.5371 | 0.029* | |
C3 | −0.0461 (3) | 0.3451 (2) | 0.52319 (9) | 0.0252 (4) | |
H3 | −0.1475 | 0.3436 | 0.4920 | 0.030* | |
C4 | −0.0081 (3) | 0.23570 (19) | 0.55482 (9) | 0.0212 (4) | |
C5 | 0.1542 (3) | 0.19118 (18) | 0.55784 (8) | 0.0189 (4) | |
H5 | 0.2275 | 0.2184 | 0.5313 | 0.023* | |
C6 | 0.2292 (3) | 0.10277 (17) | 0.59921 (8) | 0.0178 (4) | |
H6 | 0.1422 | 0.0819 | 0.6256 | 0.021* | |
C7 | 0.4028 (2) | 0.14662 (17) | 0.63311 (8) | 0.0169 (4) | |
H7 | 0.4636 | 0.1951 | 0.6067 | 0.020* | |
C8 | 0.3806 (3) | 0.22003 (17) | 0.68512 (8) | 0.0186 (4) | |
H8 | 0.4956 | 0.2564 | 0.7002 | 0.022* | |
C9 | 0.2383 (3) | 0.31119 (18) | 0.67457 (8) | 0.0184 (4) | |
H9 | 0.1176 | 0.2824 | 0.6791 | 0.022* | |
C10 | 0.2377 (3) | 0.41435 (18) | 0.63764 (8) | 0.0192 (4) | |
C11 | 0.5075 (3) | 0.03793 (17) | 0.64365 (8) | 0.0192 (4) | |
C12 | 0.4309 (3) | −0.04565 (19) | 0.59978 (9) | 0.0214 (4) | |
C13 | 0.6469 (3) | 0.0153 (2) | 0.68150 (10) | 0.0263 (4) | |
H13A | 0.7032 | −0.0575 | 0.6815 | 0.032* | |
H13B | 0.6904 | 0.0720 | 0.7086 | 0.032* | |
C14 | 0.3923 (3) | 0.44635 (18) | 0.60680 (9) | 0.0206 (4) | |
C15 | −0.1576 (3) | 0.1900 (2) | 0.58351 (11) | 0.0322 (5) | |
H15A | −0.1287 | 0.1124 | 0.5979 | 0.048* | |
H15B | −0.2650 | 0.1874 | 0.5561 | 0.048* | |
H15C | −0.1766 | 0.2405 | 0.6153 | 0.048* | |
C16 | 0.5048 (3) | 0.5918 (2) | 0.55366 (11) | 0.0345 (6) | |
H16A | 0.6180 | 0.5877 | 0.5782 | 0.052* | |
H16B | 0.4810 | 0.6716 | 0.5418 | 0.052* | |
H16C | 0.5094 | 0.5436 | 0.5200 | 0.052* | |
C17 | 0.3967 (3) | 0.1562 (2) | 0.78179 (9) | 0.0247 (4) | |
C18 | 0.3360 (3) | 0.0594 (2) | 0.81694 (8) | 0.0265 (5) | |
C19 | 0.4686 (4) | −0.0255 (3) | 0.84194 (10) | 0.0384 (6) | |
H19 | 0.4200 | −0.1033 | 0.8489 | 0.046* | |
C20 | 0.1442 (3) | 0.0270 (2) | 0.80486 (10) | 0.0305 (5) | |
H20A | 0.1177 | −0.0331 | 0.8314 | 0.046* | |
H20B | 0.1191 | −0.0016 | 0.7658 | 0.046* | |
H20C | 0.0711 | 0.0947 | 0.8095 | 0.046* | |
C21 | 0.6602 (4) | −0.0239 (4) | 0.83443 (13) | 0.0579 (10) | |
H21A | 0.6960 | 0.0549 | 0.8269 | 0.087* | |
H21B | 0.6797 | −0.0733 | 0.8023 | 0.087* | |
H21C | 0.7303 | −0.0523 | 0.8692 | 0.087* | |
O1' | 0.0386 (2) | 0.32377 (15) | 0.80503 (8) | 0.0325 (4) | |
O2' | −0.1587 (2) | 0.27579 (18) | 0.73059 (8) | 0.0408 (5) | |
O3' | 0.3925 (3) | 0.74747 (19) | 0.97808 (9) | 0.0484 (5) | |
O4' | 0.1170 (2) | 0.78812 (14) | 0.89640 (7) | 0.0291 (4) | |
O5' | −0.1968 (2) | 0.6498 (2) | 0.92501 (7) | 0.0422 (5) | |
O6' | −0.0378 (2) | 0.67878 (16) | 1.01044 (6) | 0.0324 (4) | |
O7' | 0.1772 (3) | 0.48272 (17) | 1.00935 (7) | 0.0399 (4) | |
O8' | 0.0889 (2) | 0.66154 (13) | 0.77327 (6) | 0.0232 (3) | |
O9' | −0.1085 (2) | 0.79615 (16) | 0.73917 (7) | 0.0322 (4) | |
O10' | 0.1378 (2) | 0.88097 (14) | 0.67055 (7) | 0.0288 (4) | |
C1' | 0.2801 (3) | 0.6750 (2) | 0.97469 (10) | 0.0310 (5) | |
C2' | 0.3103 (4) | 0.5696 (3) | 1.01063 (11) | 0.0389 (6) | |
H2' | 0.3791 | 0.5827 | 1.0489 | 0.047* | |
C3' | 0.3360 (4) | 0.4551 (3) | 0.98589 (12) | 0.0408 (6) | |
H3' | 0.4201 | 0.4028 | 1.0093 | 0.049* | |
C4' | 0.3201 (3) | 0.4383 (2) | 0.92300 (11) | 0.0329 (5) | |
C5' | 0.1609 (3) | 0.4155 (2) | 0.89486 (11) | 0.0297 (5) | |
H5' | 0.0744 | 0.3871 | 0.9167 | 0.036* | |
C6' | 0.1056 (3) | 0.42999 (19) | 0.83278 (10) | 0.0255 (4) | |
H6' | 0.2061 | 0.4603 | 0.8140 | 0.031* | |
C7' | −0.0517 (3) | 0.51425 (19) | 0.82377 (9) | 0.0214 (4) | |
H7' | −0.1223 | 0.5031 | 0.8560 | 0.026* | |
C8' | −0.0007 (3) | 0.64063 (19) | 0.82299 (8) | 0.0210 (4) | |
H8' | −0.1080 | 0.6902 | 0.8217 | 0.025* | |
C9' | 0.1359 (3) | 0.67680 (19) | 0.87163 (9) | 0.0225 (4) | |
H9' | 0.2597 | 0.6586 | 0.8652 | 0.027* | |
C10' | 0.1133 (3) | 0.6892 (2) | 0.93238 (9) | 0.0233 (4) | |
C11' | −0.1584 (3) | 0.4677 (2) | 0.77121 (9) | 0.0252 (4) | |
C12' | −0.1006 (3) | 0.3470 (2) | 0.76492 (10) | 0.0285 (5) | |
C13' | −0.2837 (3) | 0.5162 (3) | 0.73547 (11) | 0.0365 (6) | |
H13C | −0.3408 | 0.4736 | 0.7042 | 0.044* | |
H13D | −0.3167 | 0.5937 | 0.7410 | 0.044* | |
C14' | −0.0607 (3) | 0.6692 (2) | 0.95423 (9) | 0.0270 (5) | |
C15' | 0.4883 (3) | 0.4532 (3) | 0.89726 (14) | 0.0469 (7) | |
H15D | 0.4667 | 0.4365 | 0.8565 | 0.070* | |
H15E | 0.5780 | 0.4003 | 0.9156 | 0.070* | |
H15F | 0.5301 | 0.5325 | 0.9030 | 0.070* | |
C16' | −0.1851 (4) | 0.6423 (3) | 1.03954 (11) | 0.0406 (6) | |
H16D | −0.2917 | 0.6842 | 1.0240 | 0.061* | |
H16E | −0.1581 | 0.6585 | 1.0803 | 0.061* | |
H16F | −0.2044 | 0.5596 | 1.0339 | 0.061* | |
C17' | 0.0271 (3) | 0.74616 (19) | 0.73718 (9) | 0.0221 (4) | |
C18' | 0.1573 (3) | 0.76786 (19) | 0.69522 (9) | 0.0228 (4) | |
C19' | 0.0878 (3) | 0.78337 (19) | 0.63437 (9) | 0.0240 (4) | |
H19' | 0.1737 | 0.7639 | 0.6074 | 0.029* | |
C20' | 0.3439 (3) | 0.7284 (2) | 0.71172 (10) | 0.0294 (5) | |
H20D | 0.4147 | 0.7482 | 0.6815 | 0.044* | |
H20E | 0.3455 | 0.6449 | 0.7173 | 0.044* | |
H20F | 0.3932 | 0.7663 | 0.7471 | 0.044* | |
C21' | −0.1019 (3) | 0.7762 (2) | 0.60909 (9) | 0.0279 (5) | |
H21D | −0.1761 | 0.7670 | 0.6396 | 0.042* | |
H21E | −0.1184 | 0.7101 | 0.5833 | 0.042* | |
H21F | −0.1353 | 0.8468 | 0.5878 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0241 (7) | 0.0172 (7) | 0.0198 (7) | 0.0006 (6) | 0.0024 (5) | −0.0044 (5) |
O2 | 0.0316 (8) | 0.0197 (8) | 0.0393 (9) | 0.0041 (7) | 0.0061 (7) | −0.0060 (7) |
O3 | 0.0330 (8) | 0.0332 (9) | 0.0280 (8) | 0.0100 (8) | 0.0093 (7) | 0.0000 (7) |
O4 | 0.0349 (8) | 0.0175 (7) | 0.0184 (7) | 0.0022 (6) | 0.0014 (6) | −0.0034 (6) |
O5 | 0.0249 (8) | 0.0223 (8) | 0.0429 (10) | 0.0016 (7) | 0.0075 (7) | 0.0051 (7) |
O6 | 0.0300 (8) | 0.0178 (7) | 0.0301 (8) | 0.0002 (6) | 0.0094 (6) | 0.0022 (6) |
O7 | 0.0348 (8) | 0.0249 (8) | 0.0202 (7) | 0.0041 (7) | 0.0059 (6) | 0.0034 (6) |
O8 | 0.0267 (7) | 0.0203 (7) | 0.0152 (6) | −0.0013 (6) | −0.0003 (5) | 0.0018 (6) |
O9 | 0.0603 (12) | 0.0593 (14) | 0.0232 (8) | −0.0322 (11) | 0.0002 (8) | −0.0074 (9) |
O10 | 0.0405 (9) | 0.0518 (11) | 0.0135 (7) | 0.0097 (9) | −0.0003 (6) | 0.0000 (7) |
C1 | 0.0256 (10) | 0.0189 (10) | 0.0213 (9) | 0.0011 (8) | 0.0046 (8) | 0.0025 (8) |
C2 | 0.0277 (10) | 0.0228 (11) | 0.0227 (10) | 0.0082 (9) | 0.0026 (8) | 0.0035 (9) |
C3 | 0.0238 (10) | 0.0271 (11) | 0.0233 (10) | 0.0061 (9) | −0.0017 (8) | 0.0005 (9) |
C4 | 0.0236 (10) | 0.0218 (10) | 0.0174 (9) | −0.0002 (8) | −0.0007 (8) | −0.0021 (8) |
C5 | 0.0226 (9) | 0.0191 (9) | 0.0147 (8) | −0.0013 (8) | 0.0018 (7) | −0.0011 (7) |
C6 | 0.0206 (9) | 0.0153 (9) | 0.0179 (9) | −0.0002 (7) | 0.0034 (7) | −0.0016 (7) |
C7 | 0.0183 (8) | 0.0155 (9) | 0.0169 (8) | 0.0006 (7) | 0.0021 (7) | −0.0007 (7) |
C8 | 0.0205 (9) | 0.0171 (9) | 0.0176 (9) | −0.0016 (8) | −0.0001 (7) | 0.0005 (7) |
C9 | 0.0230 (9) | 0.0183 (10) | 0.0141 (8) | −0.0006 (8) | 0.0035 (7) | −0.0013 (7) |
C10 | 0.0246 (9) | 0.0161 (9) | 0.0169 (9) | 0.0020 (8) | 0.0026 (7) | −0.0011 (7) |
C11 | 0.0196 (9) | 0.0161 (9) | 0.0225 (9) | 0.0005 (8) | 0.0044 (8) | 0.0007 (8) |
C12 | 0.0233 (10) | 0.0179 (10) | 0.0236 (10) | −0.0006 (8) | 0.0050 (8) | −0.0001 (8) |
C13 | 0.0264 (10) | 0.0228 (11) | 0.0295 (11) | 0.0048 (9) | 0.0033 (9) | −0.0004 (9) |
C14 | 0.0232 (9) | 0.0168 (10) | 0.0213 (10) | −0.0016 (8) | 0.0012 (8) | −0.0004 (8) |
C15 | 0.0203 (10) | 0.0392 (14) | 0.0371 (13) | 0.0003 (10) | 0.0035 (9) | 0.0041 (11) |
C16 | 0.0426 (13) | 0.0194 (11) | 0.0450 (14) | −0.0030 (10) | 0.0193 (12) | 0.0021 (10) |
C17 | 0.0272 (10) | 0.0301 (12) | 0.0164 (9) | 0.0006 (9) | 0.0015 (8) | −0.0032 (8) |
C18 | 0.0345 (11) | 0.0319 (12) | 0.0127 (8) | 0.0054 (10) | 0.0012 (8) | −0.0003 (8) |
C19 | 0.0492 (14) | 0.0469 (16) | 0.0189 (11) | 0.0188 (13) | 0.0038 (10) | 0.0041 (11) |
C20 | 0.0394 (13) | 0.0287 (12) | 0.0232 (10) | −0.0042 (10) | 0.0030 (9) | 0.0056 (9) |
C21 | 0.0482 (16) | 0.093 (3) | 0.0322 (14) | 0.0318 (18) | 0.0022 (12) | 0.0055 (16) |
O1' | 0.0320 (8) | 0.0233 (8) | 0.0412 (10) | −0.0031 (7) | 0.0011 (7) | −0.0070 (7) |
O2' | 0.0382 (10) | 0.0407 (11) | 0.0444 (11) | −0.0114 (9) | 0.0088 (8) | −0.0192 (9) |
O3' | 0.0399 (11) | 0.0505 (13) | 0.0506 (12) | −0.0194 (10) | −0.0100 (9) | −0.0005 (10) |
O4' | 0.0435 (9) | 0.0199 (8) | 0.0236 (8) | −0.0050 (7) | 0.0034 (7) | 0.0006 (6) |
O5' | 0.0294 (8) | 0.0682 (14) | 0.0293 (9) | −0.0098 (9) | 0.0056 (7) | −0.0127 (9) |
O6' | 0.0359 (9) | 0.0419 (10) | 0.0201 (7) | −0.0041 (8) | 0.0063 (6) | 0.0004 (7) |
O7' | 0.0518 (11) | 0.0369 (10) | 0.0291 (9) | −0.0025 (9) | −0.0024 (8) | 0.0091 (8) |
O8' | 0.0280 (7) | 0.0239 (8) | 0.0183 (7) | 0.0038 (6) | 0.0052 (6) | 0.0039 (6) |
O9' | 0.0347 (9) | 0.0345 (10) | 0.0285 (9) | 0.0121 (8) | 0.0085 (7) | 0.0093 (7) |
O10' | 0.0434 (9) | 0.0188 (8) | 0.0249 (8) | −0.0024 (7) | 0.0063 (7) | 0.0020 (6) |
C1' | 0.0302 (11) | 0.0385 (14) | 0.0229 (10) | −0.0043 (11) | −0.0024 (9) | −0.0040 (10) |
C2' | 0.0391 (14) | 0.0446 (16) | 0.0287 (12) | 0.0003 (12) | −0.0123 (10) | 0.0031 (11) |
C3' | 0.0405 (14) | 0.0392 (15) | 0.0374 (14) | 0.0076 (12) | −0.0156 (11) | 0.0075 (12) |
C4' | 0.0323 (12) | 0.0275 (12) | 0.0367 (13) | 0.0052 (10) | −0.0042 (10) | 0.0026 (10) |
C5' | 0.0304 (11) | 0.0219 (11) | 0.0350 (12) | 0.0009 (9) | −0.0023 (9) | 0.0070 (9) |
C6' | 0.0238 (10) | 0.0216 (11) | 0.0303 (11) | −0.0014 (9) | 0.0007 (9) | −0.0010 (9) |
C7' | 0.0216 (9) | 0.0240 (10) | 0.0186 (9) | −0.0011 (8) | 0.0021 (7) | 0.0013 (8) |
C8' | 0.0244 (10) | 0.0232 (10) | 0.0158 (9) | 0.0018 (8) | 0.0041 (7) | 0.0020 (8) |
C9' | 0.0258 (10) | 0.0209 (10) | 0.0209 (9) | −0.0010 (8) | 0.0034 (8) | 0.0025 (8) |
C10' | 0.0271 (10) | 0.0246 (11) | 0.0175 (9) | −0.0050 (9) | −0.0002 (8) | 0.0017 (8) |
C11' | 0.0236 (10) | 0.0316 (12) | 0.0207 (10) | −0.0058 (9) | 0.0044 (8) | −0.0037 (9) |
C12' | 0.0264 (10) | 0.0319 (12) | 0.0284 (11) | −0.0057 (10) | 0.0085 (9) | −0.0046 (10) |
C13' | 0.0286 (11) | 0.0478 (16) | 0.0311 (12) | −0.0028 (12) | −0.0035 (9) | −0.0068 (12) |
C14' | 0.0318 (11) | 0.0290 (12) | 0.0208 (10) | −0.0026 (10) | 0.0055 (9) | −0.0010 (9) |
C15' | 0.0288 (12) | 0.0494 (18) | 0.0598 (18) | 0.0036 (13) | −0.0038 (12) | −0.0117 (15) |
C16' | 0.0456 (14) | 0.0474 (16) | 0.0326 (13) | −0.0018 (13) | 0.0192 (11) | 0.0008 (12) |
C17' | 0.0283 (11) | 0.0201 (10) | 0.0180 (9) | −0.0011 (8) | 0.0032 (8) | −0.0001 (8) |
C18' | 0.0294 (11) | 0.0187 (10) | 0.0206 (9) | −0.0005 (9) | 0.0044 (8) | 0.0023 (8) |
C19' | 0.0327 (11) | 0.0200 (10) | 0.0192 (9) | 0.0002 (9) | 0.0027 (8) | 0.0026 (8) |
C20' | 0.0249 (11) | 0.0355 (13) | 0.0281 (11) | −0.0016 (10) | 0.0052 (9) | 0.0040 (10) |
C21' | 0.0312 (11) | 0.0304 (12) | 0.0216 (10) | 0.0055 (10) | 0.0017 (9) | 0.0025 (9) |
O1—C12 | 1.362 (3) | O1'—C12' | 1.360 (3) |
O1—C6 | 1.465 (2) | O1'—C6' | 1.461 (3) |
O2—C12 | 1.202 (3) | O2'—C12' | 1.205 (3) |
O3—C1 | 1.201 (3) | O3'—C1' | 1.199 (3) |
O4—C10 | 1.442 (2) | O4'—C10' | 1.435 (3) |
O4—C9 | 1.442 (3) | O4'—C9' | 1.437 (3) |
O5—C14 | 1.192 (3) | O5'—C14' | 1.195 (3) |
O6—C14 | 1.332 (3) | O6'—C14' | 1.326 (3) |
O6—C16 | 1.451 (3) | O6'—C16' | 1.457 (3) |
O7—C2 | 1.434 (3) | O7'—C2' | 1.432 (3) |
O7—C3 | 1.435 (3) | O7'—C3' | 1.435 (4) |
O8—C17 | 1.347 (2) | O8'—C17' | 1.350 (3) |
O8—C8 | 1.450 (2) | O8'—C8' | 1.458 (2) |
O9—C17 | 1.193 (3) | O9'—C17' | 1.194 (3) |
O10—C18 | 1.436 (3) | O10'—C18' | 1.440 (3) |
O10—C19 | 1.449 (3) | O10'—C19' | 1.445 (3) |
C1—C2 | 1.499 (3) | C1'—C2' | 1.494 (4) |
C1—C10 | 1.530 (3) | C1'—C10' | 1.527 (3) |
C2—C3 | 1.494 (3) | C2'—C3' | 1.478 (4) |
C2—H2 | 1.0000 | C2'—H2' | 1.0000 |
C3—C4 | 1.487 (3) | C3'—C4' | 1.493 (4) |
C3—H3 | 1.0000 | C3'—H3' | 1.0000 |
C4—C5 | 1.338 (3) | C4'—C5' | 1.338 (3) |
C4—C15 | 1.500 (3) | C4'—C15' | 1.503 (4) |
C5—C6 | 1.485 (3) | C5'—C6' | 1.488 (3) |
C5—H5 | 0.9500 | C5'—H5' | 0.9500 |
C6—C7 | 1.547 (3) | C6'—C7' | 1.545 (3) |
C6—H6 | 1.0000 | C6'—H6' | 1.0000 |
C7—C11 | 1.500 (3) | C7'—C11' | 1.500 (3) |
C7—C8 | 1.527 (3) | C7'—C8' | 1.522 (3) |
C7—H7 | 1.0000 | C7'—H7' | 1.0000 |
C8—C9 | 1.517 (3) | C8'—C9' | 1.513 (3) |
C8—H8 | 1.0000 | C8'—H8' | 1.0000 |
C9—C10 | 1.485 (3) | C9'—C10' | 1.480 (3) |
C9—H9 | 1.0000 | C9'—H9' | 1.0000 |
C10—C14 | 1.514 (3) | C10'—C14' | 1.507 (3) |
C11—C13 | 1.329 (3) | C11'—C13' | 1.321 (3) |
C11—C12 | 1.488 (3) | C11'—C12' | 1.486 (3) |
C13—H13A | 0.9500 | C13'—H13C | 0.9500 |
C13—H13B | 0.9500 | C13'—H13D | 0.9500 |
C15—H15A | 0.9800 | C15'—H15D | 0.9800 |
C15—H15B | 0.9800 | C15'—H15E | 0.9800 |
C15—H15C | 0.9800 | C15'—H15F | 0.9800 |
C16—H16A | 0.9800 | C16'—H16D | 0.9800 |
C16—H16B | 0.9800 | C16'—H16E | 0.9800 |
C16—H16C | 0.9800 | C16'—H16F | 0.9800 |
C17—C18 | 1.509 (3) | C17'—C18' | 1.516 (3) |
C18—C19 | 1.483 (3) | C18'—C19' | 1.483 (3) |
C18—C20 | 1.506 (3) | C18'—C20' | 1.502 (3) |
C19—C21 | 1.499 (4) | C19'—C21' | 1.499 (3) |
C19—H19 | 1.0000 | C19'—H19' | 1.0000 |
C20—H20A | 0.9800 | C20'—H20D | 0.9800 |
C20—H20B | 0.9800 | C20'—H20E | 0.9800 |
C20—H20C | 0.9800 | C20'—H20F | 0.9800 |
C21—H21A | 0.9800 | C21'—H21D | 0.9800 |
C21—H21B | 0.9800 | C21'—H21E | 0.9800 |
C21—H21C | 0.9800 | C21'—H21F | 0.9800 |
C12—O1—C6 | 109.82 (15) | C12'—O1'—C6' | 110.15 (18) |
C10—O4—C9 | 61.98 (13) | C10'—O4'—C9' | 62.02 (14) |
C14—O6—C16 | 114.27 (17) | C14'—O6'—C16' | 116.2 (2) |
C2—O7—C3 | 62.74 (14) | C2'—O7'—C3' | 62.09 (18) |
C17—O8—C8 | 117.91 (16) | C17'—O8'—C8' | 118.14 (16) |
C18—O10—C19 | 61.88 (15) | C18'—O10'—C19' | 61.87 (14) |
O3—C1—C2 | 118.98 (19) | O3'—C1'—C2' | 118.8 (2) |
O3—C1—C10 | 120.39 (19) | O3'—C1'—C10' | 119.9 (2) |
C2—C1—C10 | 120.64 (17) | C2'—C1'—C10' | 121.2 (2) |
O7—C2—C3 | 58.68 (13) | O7'—C2'—C3' | 59.07 (18) |
O7—C2—C1 | 120.14 (18) | O7'—C2'—C1' | 120.6 (2) |
C3—C2—C1 | 121.80 (19) | C3'—C2'—C1' | 122.1 (2) |
O7—C2—H2 | 114.9 | O7'—C2'—H2' | 114.6 |
C3—C2—H2 | 114.9 | C3'—C2'—H2' | 114.6 |
C1—C2—H2 | 114.9 | C1'—C2'—H2' | 114.6 |
O7—C3—C4 | 117.00 (18) | O7'—C3'—C2' | 58.84 (18) |
O7—C3—C2 | 58.58 (14) | O7'—C3'—C4' | 116.9 (2) |
C4—C3—C2 | 120.49 (18) | C2'—C3'—C4' | 121.1 (2) |
O7—C3—H3 | 116.1 | O7'—C3'—H3' | 115.9 |
C4—C3—H3 | 116.1 | C2'—C3'—H3' | 115.9 |
C2—C3—H3 | 116.1 | C4'—C3'—H3' | 115.9 |
C5—C4—C3 | 118.57 (19) | C5'—C4'—C3' | 118.4 (2) |
C5—C4—C15 | 126.4 (2) | C5'—C4'—C15' | 126.3 (2) |
C3—C4—C15 | 114.88 (19) | C3'—C4'—C15' | 115.2 (2) |
C4—C5—C6 | 125.48 (19) | C4'—C5'—C6' | 126.5 (2) |
C4—C5—H5 | 117.3 | C4'—C5'—H5' | 116.7 |
C6—C5—H5 | 117.3 | C6'—C5'—H5' | 116.7 |
O1—C6—C5 | 111.04 (16) | O1'—C6'—C5' | 112.82 (19) |
O1—C6—C7 | 103.80 (15) | O1'—C6'—C7' | 104.64 (17) |
C5—C6—C7 | 110.34 (17) | C5'—C6'—C7' | 109.01 (18) |
O1—C6—H6 | 110.5 | O1'—C6'—H6' | 110.1 |
C5—C6—H6 | 110.5 | C5'—C6'—H6' | 110.1 |
C7—C6—H6 | 110.5 | C7'—C6'—H6' | 110.1 |
C11—C7—C8 | 116.67 (17) | C11'—C7'—C8' | 116.83 (18) |
C11—C7—C6 | 102.26 (16) | C11'—C7'—C6' | 102.49 (18) |
C8—C7—C6 | 115.27 (16) | C8'—C7'—C6' | 114.75 (17) |
C11—C7—H7 | 107.4 | C11'—C7'—H7' | 107.4 |
C8—C7—H7 | 107.4 | C8'—C7'—H7' | 107.4 |
C6—C7—H7 | 107.4 | C6'—C7'—H7' | 107.4 |
O8—C8—C9 | 105.89 (16) | O8'—C8'—C9' | 102.68 (16) |
O8—C8—C7 | 106.62 (16) | O8'—C8'—C7' | 108.59 (17) |
C9—C8—C7 | 114.17 (16) | C9'—C8'—C7' | 114.35 (18) |
O8—C8—H8 | 110.0 | O8'—C8'—H8' | 110.3 |
C9—C8—H8 | 110.0 | C9'—C8'—H8' | 110.3 |
C7—C8—H8 | 110.0 | C7'—C8'—H8' | 110.3 |
O4—C9—C10 | 58.99 (13) | O4'—C9'—C10' | 58.93 (14) |
O4—C9—C8 | 117.91 (17) | O4'—C9'—C8' | 117.80 (18) |
C10—C9—C8 | 127.58 (17) | C10'—C9'—C8' | 127.83 (19) |
O4—C9—H9 | 113.6 | O4'—C9'—H9' | 113.6 |
C10—C9—H9 | 113.6 | C10'—C9'—H9' | 113.6 |
C8—C9—H9 | 113.6 | C8'—C9'—H9' | 113.6 |
O4—C10—C9 | 59.02 (12) | O4'—C10'—C9' | 59.05 (13) |
O4—C10—C14 | 113.36 (17) | O4'—C10'—C14' | 114.45 (19) |
C9—C10—C14 | 122.68 (18) | C9'—C10'—C14' | 122.59 (19) |
O4—C10—C1 | 112.86 (16) | O4'—C10'—C1' | 113.48 (18) |
C9—C10—C1 | 117.70 (17) | C9'—C10'—C1' | 115.90 (19) |
C14—C10—C1 | 116.47 (17) | C14'—C10'—C1' | 117.23 (18) |
C13—C11—C12 | 123.5 (2) | C13'—C11'—C12' | 122.7 (2) |
C13—C11—C7 | 130.1 (2) | C13'—C11'—C7' | 130.6 (2) |
C12—C11—C7 | 106.30 (17) | C12'—C11'—C7' | 106.72 (19) |
O2—C12—O1 | 120.9 (2) | O2'—C12'—O1' | 121.5 (2) |
O2—C12—C11 | 129.7 (2) | O2'—C12'—C11' | 129.0 (2) |
O1—C12—C11 | 109.38 (17) | O1'—C12'—C11' | 109.5 (2) |
C11—C13—H13A | 120.0 | C11'—C13'—H13C | 120.0 |
C11—C13—H13B | 120.0 | C11'—C13'—H13D | 120.0 |
H13A—C13—H13B | 120.0 | H13C—C13'—H13D | 120.0 |
O5—C14—O6 | 125.4 (2) | O5'—C14'—O6' | 126.2 (2) |
O5—C14—C10 | 125.7 (2) | O5'—C14'—C10' | 124.9 (2) |
O6—C14—C10 | 108.88 (17) | O6'—C14'—C10' | 108.91 (19) |
C4—C15—H15A | 109.5 | C4'—C15'—H15D | 109.5 |
C4—C15—H15B | 109.5 | C4'—C15'—H15E | 109.5 |
H15A—C15—H15B | 109.5 | H15D—C15'—H15E | 109.5 |
C4—C15—H15C | 109.5 | C4'—C15'—H15F | 109.5 |
H15A—C15—H15C | 109.5 | H15D—C15'—H15F | 109.5 |
H15B—C15—H15C | 109.5 | H15E—C15'—H15F | 109.5 |
O6—C16—H16A | 109.5 | O6'—C16'—H16D | 109.5 |
O6—C16—H16B | 109.5 | O6'—C16'—H16E | 109.5 |
H16A—C16—H16B | 109.5 | H16D—C16'—H16E | 109.5 |
O6—C16—H16C | 109.5 | O6'—C16'—H16F | 109.5 |
H16A—C16—H16C | 109.5 | H16D—C16'—H16F | 109.5 |
H16B—C16—H16C | 109.5 | H16E—C16'—H16F | 109.5 |
O9—C17—O8 | 124.2 (2) | O9'—C17'—O8' | 124.41 (19) |
O9—C17—C18 | 126.7 (2) | O9'—C17'—C18' | 126.2 (2) |
O8—C17—C18 | 109.04 (18) | O8'—C17'—C18' | 109.35 (18) |
O10—C18—C19 | 59.51 (15) | O10'—C18'—C19' | 59.22 (13) |
O10—C18—C20 | 115.93 (18) | O10'—C18'—C20' | 115.50 (19) |
C19—C18—C20 | 120.5 (2) | C19'—C18'—C20' | 119.99 (19) |
O10—C18—C17 | 113.10 (19) | O10'—C18'—C17' | 112.10 (18) |
C19—C18—C17 | 118.4 (2) | C19'—C18'—C17' | 118.39 (19) |
C20—C18—C17 | 116.28 (19) | C20'—C18'—C17' | 117.39 (18) |
O10—C19—C18 | 58.61 (15) | O10'—C19'—C18' | 58.91 (13) |
O10—C19—C21 | 116.6 (3) | O10'—C19'—C21' | 116.72 (19) |
C18—C19—C21 | 124.9 (3) | C18'—C19'—C21' | 126.10 (19) |
O10—C19—H19 | 114.8 | O10'—C19'—H19' | 114.4 |
C18—C19—H19 | 114.8 | C18'—C19'—H19' | 114.4 |
C21—C19—H19 | 114.8 | C21'—C19'—H19' | 114.4 |
C18—C20—H20A | 109.5 | C18'—C20'—H20D | 109.5 |
C18—C20—H20B | 109.5 | C18'—C20'—H20E | 109.5 |
H20A—C20—H20B | 109.5 | H20D—C20'—H20E | 109.5 |
C18—C20—H20C | 109.5 | C18'—C20'—H20F | 109.5 |
H20A—C20—H20C | 109.5 | H20D—C20'—H20F | 109.5 |
H20B—C20—H20C | 109.5 | H20E—C20'—H20F | 109.5 |
C19—C21—H21A | 109.5 | C19'—C21'—H21D | 109.5 |
C19—C21—H21B | 109.5 | C19'—C21'—H21E | 109.5 |
H21A—C21—H21B | 109.5 | H21D—C21'—H21E | 109.5 |
C19—C21—H21C | 109.5 | C19'—C21'—H21F | 109.5 |
H21A—C21—H21C | 109.5 | H21D—C21'—H21F | 109.5 |
H21B—C21—H21C | 109.5 | H21E—C21'—H21F | 109.5 |
C3—O7—C2—C1 | 111.1 (2) | C3'—O7'—C2'—C1' | 111.5 (3) |
O3—C1—C2—O7 | 172.9 (2) | O3'—C1'—C2'—O7' | 177.9 (2) |
C10—C1—C2—O7 | −7.1 (3) | C10'—C1'—C2'—O7' | −4.7 (4) |
O3—C1—C2—C3 | −117.4 (2) | O3'—C1'—C2'—C3' | −111.6 (3) |
C10—C1—C2—C3 | 62.6 (3) | C10'—C1'—C2'—C3' | 65.8 (3) |
C2—O7—C3—C4 | −110.9 (2) | C2'—O7'—C3'—C4' | −111.7 (3) |
C1—C2—C3—O7 | −108.3 (2) | C1'—C2'—C3'—O7' | −109.0 (3) |
O7—C2—C3—C4 | 104.9 (2) | O7'—C2'—C3'—C4' | 104.6 (3) |
C1—C2—C3—C4 | −3.4 (3) | C1'—C2'—C3'—C4' | −4.4 (4) |
O7—C3—C4—C5 | −18.6 (3) | O7'—C3'—C4'—C5' | −19.7 (4) |
C2—C3—C4—C5 | −86.3 (3) | C2'—C3'—C4'—C5' | −87.9 (3) |
O7—C3—C4—C15 | 157.90 (19) | O7'—C3'—C4'—C15' | 158.2 (2) |
C2—C3—C4—C15 | 90.2 (2) | C2'—C3'—C4'—C15' | 90.1 (3) |
C3—C4—C5—C6 | 162.63 (19) | C3'—C4'—C5'—C6' | 160.5 (2) |
C15—C4—C5—C6 | −13.4 (3) | C15'—C4'—C5'—C6' | −17.3 (4) |
C12—O1—C6—C5 | 144.82 (17) | C12'—O1'—C6'—C5' | 141.55 (19) |
C12—O1—C6—C7 | 26.3 (2) | C12'—O1'—C6'—C7' | 23.2 (2) |
C4—C5—C6—O1 | 121.6 (2) | C4'—C5'—C6'—O1' | 123.2 (3) |
C4—C5—C6—C7 | −123.9 (2) | C4'—C5'—C6'—C7' | −121.0 (3) |
O1—C6—C7—C11 | −28.47 (18) | O1'—C6'—C7'—C11' | −25.1 (2) |
C5—C6—C7—C11 | −147.49 (16) | C5'—C6'—C7'—C11' | −146.00 (19) |
O1—C6—C7—C8 | −156.10 (16) | O1'—C6'—C7'—C8' | −152.76 (18) |
C5—C6—C7—C8 | 84.9 (2) | C5'—C6'—C7'—C8' | 86.3 (2) |
C17—O8—C8—C9 | −100.1 (2) | C17'—O8'—C8'—C9' | −112.44 (19) |
C17—O8—C8—C7 | 137.91 (17) | C17'—O8'—C8'—C7' | 126.12 (19) |
C11—C7—C8—O8 | −48.8 (2) | C11'—C7'—C8'—O8' | −54.3 (2) |
C6—C7—C8—O8 | 71.2 (2) | C6'—C7'—C8'—O8' | 65.7 (2) |
C11—C7—C8—C9 | −165.40 (17) | C11'—C7'—C8'—C9' | −168.29 (18) |
C6—C7—C8—C9 | −45.4 (2) | C6'—C7'—C8'—C9' | −48.3 (2) |
C10—O4—C9—C8 | 119.14 (19) | C10'—O4'—C9'—C8' | 119.5 (2) |
O8—C8—C9—O4 | 105.09 (18) | O8'—C8'—C9'—O4' | 100.69 (19) |
C7—C8—C9—O4 | −137.93 (17) | C7'—C8'—C9'—O4' | −141.89 (18) |
O8—C8—C9—C10 | 175.94 (18) | O8'—C8'—C9'—C10' | 171.5 (2) |
C7—C8—C9—C10 | −67.1 (3) | C7'—C8'—C9'—C10' | −71.1 (3) |
C9—O4—C10—C14 | −115.26 (19) | C9'—O4'—C10'—C14' | −114.7 (2) |
C9—O4—C10—C1 | 109.59 (19) | C9'—O4'—C10'—C1' | 107.1 (2) |
C8—C9—C10—O4 | −103.1 (2) | C8'—C9'—C10'—O4' | −102.8 (2) |
O4—C9—C10—C14 | 99.5 (2) | O4'—C9'—C10'—C14' | 100.9 (2) |
C8—C9—C10—C14 | −3.6 (3) | C8'—C9'—C10'—C14' | −1.9 (4) |
O4—C9—C10—C1 | −101.34 (19) | O4'—C9'—C10'—C1' | −103.0 (2) |
C8—C9—C10—C1 | 155.57 (19) | C8'—C9'—C10'—C1' | 154.2 (2) |
O3—C1—C10—O4 | 3.6 (3) | O3'—C1'—C10'—O4' | 5.1 (3) |
C2—C1—C10—O4 | −176.40 (18) | C2'—C1'—C10'—O4' | −172.2 (2) |
O3—C1—C10—C9 | 69.4 (3) | O3'—C1'—C10'—C9' | 70.8 (3) |
C2—C1—C10—C9 | −110.6 (2) | C2'—C1'—C10'—C9' | −106.6 (3) |
O3—C1—C10—C14 | −130.1 (2) | O3'—C1'—C10'—C14' | −131.8 (3) |
C2—C1—C10—C14 | 49.9 (3) | C2'—C1'—C10'—C14' | 50.8 (3) |
C8—C7—C11—C13 | −34.8 (3) | C8'—C7'—C11'—C13' | −36.0 (3) |
C6—C7—C11—C13 | −161.6 (2) | C6'—C7'—C11'—C13' | −162.3 (2) |
C8—C7—C11—C12 | 148.26 (17) | C8'—C7'—C11'—C12' | 145.28 (18) |
C6—C7—C11—C12 | 21.52 (19) | C6'—C7'—C11'—C12' | 18.9 (2) |
C6—O1—C12—O2 | 169.49 (19) | C6'—O1'—C12'—O2' | 167.9 (2) |
C6—O1—C12—C11 | −12.8 (2) | C6'—O1'—C12'—C11' | −11.3 (2) |
C13—C11—C12—O2 | −6.3 (4) | C13'—C11'—C12'—O2' | −3.7 (4) |
C7—C11—C12—O2 | 170.9 (2) | C7'—C11'—C12'—O2' | 175.1 (2) |
C13—C11—C12—O1 | 176.30 (19) | C13'—C11'—C12'—O1' | 175.3 (2) |
C7—C11—C12—O1 | −6.5 (2) | C7'—C11'—C12'—O1' | −5.8 (2) |
C16—O6—C14—O5 | 2.8 (3) | C16'—O6'—C14'—O5' | 11.5 (4) |
C16—O6—C14—C10 | −179.70 (18) | C16'—O6'—C14'—C10' | −169.5 (2) |
O4—C10—C14—O5 | 74.4 (3) | O4'—C10'—C14'—O5' | 62.3 (3) |
C9—C10—C14—O5 | 7.3 (3) | C9'—C10'—C14'—O5' | −5.3 (4) |
C1—C10—C14—O5 | −152.1 (2) | C1'—C10'—C14'—O5' | −161.1 (3) |
O4—C10—C14—O6 | −103.05 (19) | O4'—C10'—C14'—O6' | −116.6 (2) |
C9—C10—C14—O6 | −170.16 (18) | C9'—C10'—C14'—O6' | 175.7 (2) |
C1—C10—C14—O6 | 30.4 (2) | C1'—C10'—C14'—O6' | 20.0 (3) |
C8—O8—C17—O9 | 5.7 (3) | C8'—O8'—C17'—O9' | −9.5 (3) |
C8—O8—C17—C18 | −173.30 (17) | C8'—O8'—C17'—C18' | 169.62 (17) |
C19—O10—C18—C20 | 111.7 (3) | C19'—O10'—C18'—C20' | 111.1 (2) |
C19—O10—C18—C17 | −110.4 (2) | C19'—O10'—C18'—C17' | −110.8 (2) |
O9—C17—C18—O10 | 1.0 (3) | O9'—C17'—C18'—O10' | 21.3 (3) |
O8—C17—C18—O10 | 179.94 (17) | O8'—C17'—C18'—O10' | −157.75 (17) |
O9—C17—C18—C19 | −65.7 (3) | O9'—C17'—C18'—C19' | −44.6 (3) |
O8—C17—C18—C19 | 113.3 (2) | O8'—C17'—C18'—C19' | 136.36 (19) |
O9—C17—C18—C20 | 138.8 (3) | O9'—C17'—C18'—C20' | 158.5 (2) |
O8—C17—C18—C20 | −42.3 (3) | O8'—C17'—C18'—C20' | −20.6 (3) |
C18—O10—C19—C21 | 116.4 (3) | C18'—O10'—C19'—C21' | 117.8 (2) |
C20—C18—C19—O10 | −104.0 (2) | C20'—C18'—C19'—O10' | −103.6 (2) |
C17—C18—C19—O10 | 101.5 (2) | C17'—C18'—C19'—O10' | 100.1 (2) |
O10—C18—C19—C21 | −102.3 (3) | O10'—C18'—C19'—C21' | −102.1 (3) |
C20—C18—C19—C21 | 153.7 (3) | C20'—C18'—C19'—C21' | 154.3 (2) |
C17—C18—C19—C21 | −0.8 (4) | C17'—C18'—C19'—C21' | −2.0 (3) |