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The title compound, C24H28O9, was prepared from macrocalyxin A and is built up from five fused rings, viz. three six-membered rings and two five-membered rings. Two unique mol­ecules are present in the asymmetric unit; both independent mol­ecules have the same absolute configuration, which was deduced from the chirality of the starting material.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000328/ww6454sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000328/ww6454Isup2.hkl
Contains datablock I

CCDC reference: 298571

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.103
  • Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found




Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.778 1.000 Tmin(prime) and Tmax expected: 0.948 0.984 RR(prime) = 0.807 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.72 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 5153 Count of symmetry unique reflns 5192 Completeness (_total/calc) 99.25% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(19R)-5,19-Bis(acetyloxy)-10,13-dideoxy-10-oxo-5β-enmein top
Crystal data top
C24H28O9F(000) = 976
Mr = 460.46Dx = 1.347 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4846 reflections
a = 13.4851 (13) Åθ = 4.5–47.6°
b = 12.7578 (12) ŵ = 0.10 mm1
c = 13.6537 (13) ÅT = 293 K
β = 104.796 (2)°Plate, colourless
V = 2271.1 (4) Å30.50 × 0.49 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
5153 independent reflections
Radiation source: fine-focus sealed tube3988 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.092
φ and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1716
Tmin = 0.778, Tmax = 1.000k = 1616
13256 measured reflectionsl = 817
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
5153 reflections(Δ/σ)max = 0.050
603 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.21 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5230 (2)0.0194 (2)0.1343 (2)0.0773 (7)
O20.4804 (3)0.0428 (2)0.0741 (3)0.1005 (10)
O30.41617 (14)0.21791 (17)0.03507 (14)0.0514 (5)
O40.51939 (18)0.2551 (2)0.18735 (16)0.0658 (6)
O50.68963 (14)0.31886 (15)0.03952 (13)0.0436 (4)
O60.7613 (3)0.3904 (3)0.1538 (2)0.1185 (13)
O70.9210 (2)0.0450 (3)0.11726 (19)0.0915 (9)
O90.8282 (2)0.0345 (2)0.0272 (2)0.0783 (8)
O160.67477 (16)0.0928 (2)0.17131 (15)0.0628 (6)
O1'0.07463 (16)0.4541 (2)0.45155 (18)0.0647 (6)
O2'0.09419 (17)0.50388 (19)0.24111 (17)0.0615 (6)
O3'0.12108 (13)0.67906 (16)0.44771 (14)0.0473 (5)
O4'0.0477 (2)0.6348 (3)0.60807 (17)0.0969 (11)
O5'0.19787 (13)0.74664 (15)0.48179 (13)0.0438 (4)
O6'0.3042 (2)0.8619 (3)0.4408 (2)0.0938 (9)
O7'0.3685 (2)0.5239 (3)0.2671 (2)0.0933 (9)
O9'0.24116 (19)0.4271 (2)0.29275 (17)0.0685 (6)
O16'0.08955 (14)0.46006 (17)0.52316 (15)0.0516 (5)
C10.4839 (3)0.0513 (3)0.0746 (3)0.0615 (9)
C20.4208 (2)0.1232 (3)0.1511 (2)0.0603 (9)
C30.4590 (2)0.2314 (3)0.1234 (2)0.0504 (7)
H30.40290.28240.14110.060*
C40.5456 (2)0.2602 (3)0.1733 (2)0.0505 (7)
H4A0.53430.22380.23760.061*
H4B0.54290.33480.18710.061*
C50.6518 (2)0.2325 (2)0.10825 (18)0.0429 (6)
H50.69780.22400.15290.051*
C60.65664 (19)0.1326 (2)0.0459 (2)0.0424 (6)
H60.65100.07480.09430.051*
C70.7570 (2)0.1121 (2)0.0364 (2)0.0457 (7)
C80.7726 (3)0.0076 (3)0.0459 (3)0.0651 (9)
H8A0.81150.02630.11370.078*
H8B0.70710.04360.03120.078*
C100.8726 (3)0.0495 (3)0.0545 (2)0.0644 (9)
C110.8538 (2)0.1447 (3)0.0040 (2)0.0531 (7)
H110.83750.20470.04210.064*
C120.9525 (2)0.1706 (3)0.0911 (2)0.0659 (10)
C130.9201 (2)0.2305 (3)0.1752 (2)0.0671 (9)
H13A0.98030.24460.23000.080*
H13B0.89060.29730.14890.080*
C140.8423 (2)0.1697 (3)0.2166 (2)0.0646 (9)
H14A0.86880.10050.23820.077*
H14B0.82960.20610.27460.077*
C150.7450 (2)0.1604 (3)0.13536 (19)0.0492 (7)
H150.71410.23010.12110.059*
C170.5833 (2)0.0729 (2)0.1067 (2)0.0549 (8)
C180.5608 (2)0.1201 (2)0.0010 (2)0.0450 (6)
C190.5026 (2)0.2255 (2)0.0090 (2)0.0412 (6)
H190.54770.28470.01790.049*
C200.3471 (3)0.0878 (5)0.2280 (3)0.1017 (17)
H20A0.33390.01630.23500.122*
H20B0.30870.13450.27500.122*
C211.0149 (3)0.0731 (4)0.1349 (3)0.0911 (14)
H21A1.03520.03650.08180.127*
H21B0.97360.02770.16450.127*
H21C1.07480.09400.18590.127*
C221.0205 (3)0.2419 (5)0.0460 (3)0.0947 (15)
H22A0.98410.30530.02180.122*
H22B1.03820.20660.00930.122*
H22C1.08190.25850.09710.122*
C230.4351 (2)0.2381 (3)0.1353 (2)0.0524 (7)
C240.3398 (3)0.2353 (5)0.1714 (3)0.0973 (15)
H24A0.35180.27030.23560.126*
H24B0.32080.16380.17880.126*
H24C0.28550.27010.12310.126*
C250.7389 (3)0.3963 (3)0.0739 (3)0.0611 (8)
C260.7633 (3)0.4840 (3)0.0019 (3)0.0723 (10)
H26A0.76660.45910.06510.109*
H26B0.71100.53670.02040.109*
H26C0.82840.51360.00360.109*
C1'0.0637 (2)0.5823 (2)0.2863 (2)0.0433 (6)
C2'0.0895 (2)0.6926 (2)0.2532 (2)0.0450 (6)
C3'0.0350 (2)0.7640 (2)0.3375 (2)0.0437 (6)
H3'0.07730.82520.34260.052*
C4'0.0717 (2)0.7980 (2)0.3272 (2)0.0473 (7)
H4'10.06910.80530.25590.057*
H4'20.08800.86610.35870.057*
C5'0.1572 (2)0.7213 (2)0.3751 (2)0.0414 (6)
H5'0.21250.72910.34110.050*
C6'0.12280 (19)0.6067 (2)0.36663 (19)0.0370 (5)
H6'0.11190.58860.29490.044*
C7'0.20036 (19)0.5253 (2)0.42501 (19)0.0369 (6)
C8'0.1799 (2)0.4222 (2)0.3655 (2)0.0515 (7)
H8'10.20010.36280.41050.062*
H8'20.10770.41560.33130.062*
C10'0.3136 (3)0.5025 (3)0.3201 (2)0.0616 (9)
C11'0.31215 (19)0.5482 (2)0.4211 (2)0.0462 (7)
H11'0.32210.62420.41940.055*
C12'0.3999 (2)0.4999 (3)0.5057 (2)0.0529 (7)
C13'0.3711 (2)0.5064 (3)0.6072 (2)0.0564 (7)
H13C0.42420.47270.65910.068*
H13D0.36820.57950.62580.068*
C14'0.2690 (2)0.4551 (3)0.6041 (2)0.0502 (7)
H14C0.26960.38280.58220.060*
H14D0.25690.45580.67110.060*
C15'0.18564 (19)0.5149 (2)0.53118 (19)0.0413 (6)
H15'0.18070.58510.55860.050*
C17'0.0055 (2)0.4964 (2)0.4565 (2)0.0469 (7)
C18'0.01451 (18)0.5898 (2)0.39108 (19)0.0381 (6)
C19'0.02093 (19)0.6941 (2)0.4304 (2)0.0410 (6)
H19'0.02910.72200.48980.049*
C20'0.1498 (3)0.7173 (3)0.1652 (2)0.0698 (9)
H20C0.17910.66480.11970.084*
H20D0.16360.78730.14810.084*
C21'0.4264 (3)0.3868 (3)0.4855 (3)0.0698 (10)
H21D0.44730.38360.42350.105*
H21E0.36720.34320.48010.105*
H21F0.48130.36250.54040.105*
C22'0.4967 (3)0.5661 (4)0.5124 (4)0.0846 (12)
H22D0.55190.53960.56570.127*
H22E0.48330.63770.52650.127*
H22F0.51550.56230.44920.127*
C23'0.1232 (2)0.6464 (3)0.5414 (3)0.0617 (9)
C24'0.2295 (3)0.6246 (4)0.5484 (3)0.0773 (11)
H24D0.23430.63780.61630.116*
H24E0.24620.55270.53130.116*
H24F0.27660.66930.50230.116*
C25'0.2720 (2)0.8199 (3)0.5043 (3)0.0536 (7)
C26'0.3037 (2)0.8418 (3)0.6141 (3)0.0689 (9)
H26D0.35160.89910.62670.103*
H26E0.33570.78070.64950.103*
H26F0.24460.86010.63750.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0866 (16)0.0635 (15)0.0985 (18)0.0066 (14)0.0542 (15)0.0199 (14)
O20.125 (2)0.0476 (16)0.145 (3)0.0316 (16)0.064 (2)0.0318 (17)
O30.0422 (9)0.0590 (12)0.0562 (11)0.0024 (9)0.0180 (9)0.0172 (10)
O40.0694 (14)0.0766 (16)0.0504 (12)0.0078 (13)0.0133 (11)0.0096 (12)
O50.0493 (10)0.0420 (10)0.0411 (10)0.0057 (9)0.0146 (8)0.0029 (8)
O60.181 (3)0.117 (3)0.0814 (19)0.082 (3)0.076 (2)0.0192 (18)
O70.0773 (15)0.141 (3)0.0667 (15)0.0241 (18)0.0380 (13)0.0107 (16)
O90.0860 (17)0.0728 (17)0.0872 (17)0.0303 (15)0.0424 (15)0.0015 (14)
O160.0608 (12)0.0808 (16)0.0560 (12)0.0180 (12)0.0318 (10)0.0277 (12)
O1'0.0432 (11)0.0642 (14)0.0881 (16)0.0106 (11)0.0193 (11)0.0190 (13)
O2'0.0631 (13)0.0494 (12)0.0628 (13)0.0046 (11)0.0010 (10)0.0175 (11)
O3'0.0330 (9)0.0578 (12)0.0535 (11)0.0004 (9)0.0154 (8)0.0094 (9)
O4'0.0714 (15)0.176 (3)0.0447 (13)0.036 (2)0.0171 (12)0.0032 (16)
O5'0.0405 (9)0.0410 (10)0.0503 (10)0.0078 (9)0.0124 (8)0.0059 (8)
O6'0.0921 (18)0.100 (2)0.0873 (18)0.0562 (17)0.0190 (15)0.0038 (16)
O7'0.0921 (17)0.123 (3)0.0840 (17)0.0273 (19)0.0580 (15)0.0275 (18)
O9'0.0801 (15)0.0719 (16)0.0594 (13)0.0173 (14)0.0286 (11)0.0140 (12)
O16'0.0398 (10)0.0575 (12)0.0609 (12)0.0005 (9)0.0188 (9)0.0222 (10)
C10.068 (2)0.0464 (19)0.082 (2)0.0164 (16)0.0408 (19)0.0224 (17)
C20.0539 (17)0.073 (2)0.0580 (18)0.0203 (17)0.0213 (15)0.0269 (17)
C30.0433 (14)0.0580 (18)0.0469 (15)0.0074 (14)0.0059 (12)0.0082 (14)
C40.0554 (16)0.0531 (18)0.0390 (14)0.0033 (14)0.0047 (12)0.0019 (13)
C50.0482 (14)0.0464 (15)0.0352 (13)0.0018 (13)0.0129 (11)0.0002 (12)
C60.0474 (14)0.0408 (14)0.0423 (14)0.0036 (12)0.0175 (12)0.0018 (12)
C70.0499 (15)0.0500 (17)0.0426 (14)0.0093 (13)0.0216 (12)0.0092 (13)
C80.076 (2)0.057 (2)0.070 (2)0.0280 (18)0.0331 (18)0.0153 (17)
C100.0570 (18)0.087 (3)0.0529 (18)0.0207 (19)0.0219 (16)0.0002 (18)
C110.0487 (15)0.070 (2)0.0461 (16)0.0096 (16)0.0220 (13)0.0042 (15)
C120.0452 (15)0.097 (3)0.0580 (19)0.0110 (18)0.0189 (14)0.0031 (18)
C130.0522 (16)0.093 (3)0.0538 (17)0.0124 (19)0.0087 (14)0.0091 (19)
C140.0608 (18)0.095 (3)0.0409 (15)0.0242 (19)0.0182 (14)0.0056 (17)
C150.0512 (15)0.0615 (19)0.0403 (15)0.0151 (15)0.0218 (13)0.0104 (14)
C170.0638 (19)0.0443 (17)0.0671 (19)0.0063 (15)0.0362 (17)0.0108 (15)
C180.0487 (15)0.0389 (15)0.0538 (16)0.0009 (12)0.0248 (13)0.0002 (13)
C190.0385 (12)0.0391 (15)0.0470 (14)0.0017 (12)0.0126 (11)0.0070 (12)
C200.082 (3)0.141 (5)0.085 (3)0.041 (3)0.027 (2)0.057 (3)
C210.066 (2)0.132 (4)0.075 (2)0.049 (3)0.0165 (18)0.010 (3)
C220.0516 (18)0.148 (5)0.087 (3)0.017 (3)0.0234 (19)0.002 (3)
C230.0565 (17)0.0501 (17)0.0534 (17)0.0017 (15)0.0189 (15)0.0126 (14)
C240.078 (2)0.135 (4)0.096 (3)0.000 (3)0.052 (2)0.037 (3)
C250.0668 (19)0.059 (2)0.0596 (19)0.0196 (17)0.0202 (16)0.0044 (16)
C260.075 (2)0.056 (2)0.087 (2)0.0211 (18)0.024 (2)0.0038 (18)
C1'0.0389 (13)0.0465 (16)0.0442 (14)0.0013 (13)0.0101 (11)0.0093 (13)
C2'0.0404 (14)0.0454 (16)0.0489 (16)0.0036 (12)0.0106 (12)0.0016 (13)
C3'0.0409 (13)0.0384 (14)0.0510 (16)0.0071 (12)0.0101 (12)0.0043 (12)
C4'0.0506 (15)0.0394 (15)0.0523 (16)0.0023 (13)0.0137 (13)0.0029 (13)
C5'0.0444 (14)0.0386 (14)0.0450 (14)0.0003 (12)0.0181 (12)0.0016 (12)
C6'0.0390 (12)0.0375 (14)0.0369 (12)0.0017 (11)0.0144 (10)0.0022 (11)
C7'0.0357 (12)0.0367 (14)0.0398 (13)0.0005 (11)0.0125 (11)0.0004 (11)
C8'0.0541 (16)0.0425 (16)0.0584 (17)0.0064 (14)0.0152 (14)0.0028 (14)
C10'0.0574 (17)0.075 (2)0.0609 (19)0.0246 (19)0.0310 (16)0.0160 (18)
C11'0.0419 (14)0.0435 (15)0.0608 (17)0.0044 (12)0.0267 (13)0.0049 (13)
C12'0.0370 (14)0.0567 (18)0.0675 (19)0.0012 (14)0.0179 (13)0.0012 (16)
C13'0.0439 (14)0.069 (2)0.0515 (16)0.0029 (16)0.0031 (13)0.0045 (16)
C14'0.0503 (15)0.0573 (18)0.0451 (15)0.0084 (14)0.0162 (13)0.0095 (14)
C15'0.0410 (13)0.0435 (15)0.0433 (14)0.0020 (12)0.0181 (12)0.0034 (12)
C17'0.0425 (14)0.0475 (16)0.0545 (16)0.0025 (13)0.0195 (13)0.0062 (14)
C18'0.0327 (12)0.0391 (14)0.0439 (13)0.0022 (11)0.0123 (11)0.0033 (12)
C19'0.0342 (12)0.0464 (15)0.0437 (14)0.0037 (11)0.0123 (11)0.0084 (12)
C20'0.080 (2)0.055 (2)0.062 (2)0.0000 (18)0.0037 (17)0.0037 (17)
C21'0.0527 (18)0.067 (2)0.091 (2)0.0187 (17)0.0212 (17)0.0061 (19)
C22'0.0385 (15)0.097 (3)0.118 (3)0.0081 (18)0.0192 (17)0.015 (3)
C23'0.0515 (17)0.081 (2)0.059 (2)0.0119 (17)0.0246 (16)0.0184 (17)
C24'0.0628 (19)0.076 (3)0.108 (3)0.0101 (19)0.050 (2)0.010 (2)
C25'0.0424 (15)0.0428 (16)0.074 (2)0.0087 (14)0.0107 (15)0.0029 (16)
C26'0.0530 (18)0.066 (2)0.078 (2)0.0104 (17)0.0011 (16)0.0148 (18)
Geometric parameters (Å, º) top
O1—C171.193 (3)C21—H21B0.9600
O2—C11.202 (4)C21—H21C0.9600
O3—C231.351 (3)C22—H22A0.9600
O3—C191.445 (3)C22—H22B0.9600
O4—C231.196 (4)C22—H22C0.9600
O5—C251.341 (4)C23—C241.490 (5)
O5—C51.453 (3)C24—H24A0.9600
O6—C251.205 (4)C24—H24B0.9600
O7—C101.204 (4)C24—H24C0.9600
O9—C101.326 (5)C25—C261.470 (5)
O9—C81.435 (4)C26—H26A0.9600
O16—C171.344 (4)C26—H26B0.9600
O16—C151.456 (4)C26—H26C0.9600
O1'—C17'1.195 (3)C1'—C2'1.491 (4)
O2'—C1'1.192 (4)C1'—C18'1.549 (4)
O3'—C23'1.353 (4)C2'—C20'1.306 (4)
O3'—C19'1.442 (3)C2'—C3'1.504 (4)
O4'—C23'1.189 (4)C3'—C19'1.523 (4)
O5'—C25'1.345 (3)C3'—C4'1.542 (4)
O5'—C5'1.455 (3)C3'—H3'0.9800
O6'—C25'1.192 (4)C4'—C5'1.526 (4)
O7'—C10'1.191 (4)C4'—H4'10.9700
O9'—C10'1.354 (5)C4'—H4'20.9700
O9'—C8'1.446 (4)C5'—C6'1.529 (4)
O16'—C17'1.342 (3)C5'—H5'0.9800
O16'—C15'1.452 (3)C6'—C7'1.543 (4)
C1—C21.483 (5)C6'—C18'1.594 (3)
C1—C181.539 (4)C6'—H6'0.9800
C2—C201.327 (5)C7'—C15'1.518 (3)
C2—C31.489 (5)C7'—C8'1.534 (4)
C3—C191.524 (4)C7'—C11'1.550 (3)
C3—C41.540 (4)C8'—H8'10.9700
C3—H30.9800C8'—H8'20.9700
C4—C51.521 (4)C10'—C11'1.502 (4)
C4—H4A0.9700C11'—C12'1.555 (4)
C4—H4B0.9700C11'—H11'0.9800
C5—C61.525 (4)C12'—C21'1.528 (5)
C5—H50.9800C12'—C13'1.534 (4)
C6—C71.544 (4)C12'—C22'1.538 (5)
C6—C181.590 (4)C13'—C14'1.515 (4)
C6—H60.9800C13'—H13C0.9700
C7—C151.531 (4)C13'—H13D0.9700
C7—C111.538 (4)C14'—C15'1.505 (4)
C7—C81.543 (5)C14'—H14C0.9700
C8—H8A0.9700C14'—H14D0.9700
C8—H8B0.9700C15'—H15'0.9800
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C11—C121.577 (5)C18'—C19'1.554 (4)
C11—H110.9800C19'—H19'0.9800
C12—C221.528 (6)C20'—H20C0.9300
C12—C131.533 (5)C20'—H20D0.9300
C12—C211.535 (6)C21'—H21D0.9600
C13—C141.524 (5)C21'—H21E0.9600
C13—H13A0.9700C21'—H21F0.9600
C13—H13B0.9700C22'—H22D0.9600
C14—C151.491 (4)C22'—H22E0.9600
C14—H14A0.9700C22'—H22F0.9600
C14—H14B0.9700C23'—C24'1.486 (4)
C15—H150.9800C24'—H24D0.9600
C17—C181.521 (4)C24'—H24E0.9600
C18—C191.545 (4)C24'—H24F0.9600
C19—H190.9800C25'—C26'1.477 (5)
C20—H20A0.9300C26'—H26D0.9600
C20—H20B0.9300C26'—H26E0.9600
C21—H21A0.9600C26'—H26F0.9600
C23—O3—C19116.4 (2)H26A—C26—H26B109.5
C25—O5—C5117.1 (2)C25—C26—H26C109.5
C10—O9—C8110.8 (3)H26A—C26—H26C109.5
C17—O16—C15117.2 (2)H26B—C26—H26C109.5
C23'—O3'—C19'116.3 (2)O2'—C1'—C2'127.8 (3)
C25'—O5'—C5'116.8 (2)O2'—C1'—C18'126.4 (3)
C10'—O9'—C8'109.8 (2)C2'—C1'—C18'105.8 (2)
C17'—O16'—C15'117.9 (2)C20'—C2'—C1'123.3 (3)
O2—C1—C2127.3 (4)C20'—C2'—C3'128.7 (3)
O2—C1—C18125.9 (4)C1'—C2'—C3'108.0 (2)
C2—C1—C18106.7 (3)C2'—C3'—C19'102.4 (2)
C20—C2—C1121.7 (4)C2'—C3'—C4'112.7 (2)
C20—C2—C3131.1 (4)C19'—C3'—C4'108.7 (2)
C1—C2—C3107.1 (2)C2'—C3'—H3'110.9
C2—C3—C19103.5 (3)C19'—C3'—H3'110.9
C2—C3—C4111.1 (3)C4'—C3'—H3'110.9
C19—C3—C4109.1 (2)C5'—C4'—C3'113.6 (2)
C2—C3—H3111.0C5'—C4'—H4'1108.8
C19—C3—H3111.0C3'—C4'—H4'1108.8
C4—C3—H3111.0C5'—C4'—H4'2108.8
C5—C4—C3113.2 (2)C3'—C4'—H4'2108.8
C5—C4—H4A108.9H4'1—C4'—H4'2107.7
C3—C4—H4A108.9O5'—C5'—C4'109.7 (2)
C5—C4—H4B108.9O5'—C5'—C6'108.6 (2)
C3—C4—H4B108.9C4'—C5'—C6'113.5 (2)
H4A—C4—H4B107.8O5'—C5'—H5'108.3
O5—C5—C4108.9 (2)C4'—C5'—H5'108.3
O5—C5—C6108.38 (19)C6'—C5'—H5'108.3
C4—C5—C6114.8 (2)C5'—C6'—C7'116.8 (2)
O5—C5—H5108.2C5'—C6'—C18'112.9 (2)
C4—C5—H5108.2C7'—C6'—C18'109.7 (2)
C6—C5—H5108.2C5'—C6'—H6'105.4
C5—C6—C7116.9 (2)C7'—C6'—H6'105.4
C5—C6—C18112.7 (2)C18'—C6'—H6'105.4
C7—C6—C18110.0 (2)C15'—C7'—C8'112.4 (2)
C5—C6—H6105.4C15'—C7'—C6'108.4 (2)
C7—C6—H6105.4C8'—C7'—C6'107.3 (2)
C18—C6—H6105.4C15'—C7'—C11'114.5 (2)
C15—C7—C11115.7 (3)C8'—C7'—C11'100.8 (2)
C15—C7—C8111.6 (2)C6'—C7'—C11'113.1 (2)
C11—C7—C8100.6 (2)O9'—C8'—C7'105.7 (2)
C15—C7—C6107.7 (2)O9'—C8'—H8'1110.6
C11—C7—C6113.3 (2)C7'—C8'—H8'1110.6
C8—C7—C6107.7 (3)O9'—C8'—H8'2110.6
O9—C8—C7105.2 (3)C7'—C8'—H8'2110.6
O9—C8—H8A110.7H8'1—C8'—H8'2108.7
C7—C8—H8A110.7O7'—C10'—O9'120.8 (4)
O9—C8—H8B110.7O7'—C10'—C11'128.7 (4)
C7—C8—H8B110.7O9'—C10'—C11'110.6 (3)
H8A—C8—H8B108.8C10'—C11'—C7'101.5 (2)
O7—C10—O9121.8 (4)C10'—C11'—C12'110.1 (2)
O7—C10—C11127.5 (4)C7'—C11'—C12'117.6 (2)
O9—C10—C11110.6 (2)C10'—C11'—H11'109.1
C10—C11—C7101.8 (3)C7'—C11'—H11'109.1
C10—C11—C12110.1 (3)C12'—C11'—H11'109.1
C7—C11—C12117.0 (2)C21'—C12'—C13'109.8 (3)
C10—C11—H11109.2C21'—C12'—C22'107.2 (3)
C7—C11—H11109.2C13'—C12'—C22'108.9 (3)
C12—C11—H11109.2C21'—C12'—C11'114.1 (3)
C22—C12—C13108.7 (4)C13'—C12'—C11'109.2 (2)
C22—C12—C21108.3 (3)C22'—C12'—C11'107.5 (3)
C13—C12—C21110.2 (3)C14'—C13'—C12'112.9 (3)
C22—C12—C11107.4 (3)C14'—C13'—H13C109.0
C13—C12—C11108.8 (2)C12'—C13'—H13C109.0
C21—C12—C11113.4 (3)C14'—C13'—H13D109.0
C14—C13—C12112.3 (3)C12'—C13'—H13D109.0
C14—C13—H13A109.2H13C—C13'—H13D107.8
C12—C13—H13A109.2C15'—C14'—C13'108.7 (2)
C14—C13—H13B109.2C15'—C14'—H14C110.0
C12—C13—H13B109.2C13'—C14'—H14C110.0
H13A—C13—H13B107.9C15'—C14'—H14D110.0
C15—C14—C13108.9 (2)C13'—C14'—H14D110.0
C15—C14—H14A109.9H14C—C14'—H14D108.3
C13—C14—H14A109.9O16'—C15'—C14'107.9 (2)
C15—C14—H14B109.9O16'—C15'—C7'107.6 (2)
C13—C14—H14B109.9C14'—C15'—C7'114.7 (2)
H14A—C14—H14B108.3O16'—C15'—H15'108.8
O16—C15—C14108.7 (2)C14'—C15'—H15'108.8
O16—C15—C7106.5 (2)C7'—C15'—H15'108.8
C14—C15—C7114.7 (2)O1'—C17'—O16'118.5 (3)
O16—C15—H15108.9O1'—C17'—C18'122.1 (3)
C14—C15—H15108.9O16'—C17'—C18'119.4 (2)
C7—C15—H15108.9C17'—C18'—C1'111.0 (2)
O1—C17—O16119.1 (3)C17'—C18'—C19'113.1 (2)
O1—C17—C18122.6 (3)C1'—C18'—C19'100.1 (2)
O16—C17—C18118.3 (2)C17'—C18'—C6'116.5 (2)
C17—C18—C1110.4 (3)C1'—C18'—C6'105.00 (19)
C17—C18—C19113.7 (2)C19'—C18'—C6'109.6 (2)
C1—C18—C19101.3 (2)O3'—C19'—C3'107.0 (2)
C17—C18—C6115.9 (2)O3'—C19'—C18'109.1 (2)
C1—C18—C6105.4 (2)C3'—C19'—C18'101.4 (2)
C19—C18—C6108.9 (2)O3'—C19'—H19'112.9
O3—C19—C3106.8 (2)C3'—C19'—H19'112.9
O3—C19—C18110.5 (2)C18'—C19'—H19'112.9
C3—C19—C18100.9 (2)C2'—C20'—H20C120.0
O3—C19—H19112.6C2'—C20'—H20D120.0
C3—C19—H19112.6H20C—C20'—H20D120.0
C18—C19—H19112.6C12'—C21'—H21D109.5
C2—C20—H20A120.0C12'—C21'—H21E109.5
C2—C20—H20B120.0H21D—C21'—H21E109.5
H20A—C20—H20B120.0C12'—C21'—H21F109.5
C12—C21—H21A109.5H21D—C21'—H21F109.5
C12—C21—H21B109.5H21E—C21'—H21F109.5
H21A—C21—H21B109.5C12'—C22'—H22D109.5
C12—C21—H21C109.5C12'—C22'—H22E109.5
H21A—C21—H21C109.5H22D—C22'—H22E109.5
H21B—C21—H21C109.5C12'—C22'—H22F109.5
C12—C22—H22A109.5H22D—C22'—H22F109.5
C12—C22—H22B109.5H22E—C22'—H22F109.5
H22A—C22—H22B109.5O4'—C23'—O3'122.8 (3)
C12—C22—H22C109.5O4'—C23'—C24'125.3 (4)
H22A—C22—H22C109.5O3'—C23'—C24'111.9 (3)
H22B—C22—H22C109.5C23'—C24'—H24D109.5
O4—C23—O3122.8 (3)C23'—C24'—H24E109.5
O4—C23—C24125.2 (3)H24D—C24'—H24E109.5
O3—C23—C24112.0 (3)C23'—C24'—H24F109.5
C23—C24—H24A109.5H24D—C24'—H24F109.5
C23—C24—H24B109.5H24E—C24'—H24F109.5
H24A—C24—H24B109.5O6'—C25'—O5'122.2 (3)
C23—C24—H24C109.5O6'—C25'—C26'126.0 (3)
H24A—C24—H24C109.5O5'—C25'—C26'111.7 (3)
H24B—C24—H24C109.5C25'—C26'—H26D109.5
O6—C25—O5122.1 (3)C25'—C26'—H26E109.5
O6—C25—C26125.9 (3)H26D—C26'—H26E109.5
O5—C25—C26111.9 (3)C25'—C26'—H26F109.5
C25—C26—H26A109.5H26D—C26'—H26F109.5
C25—C26—H26B109.5H26E—C26'—H26F109.5
O2—C1—C2—C203.4 (5)O2'—C1'—C2'—C20'1.8 (5)
C18—C1—C2—C20179.5 (3)C18'—C1'—C2'—C20'176.4 (3)
O2—C1—C2—C3175.5 (3)O2'—C1'—C2'—C3'178.1 (3)
C18—C1—C2—C30.6 (3)C18'—C1'—C2'—C3'3.7 (3)
C20—C2—C3—C19153.6 (3)C20'—C2'—C3'—C19'154.7 (3)
C1—C2—C3—C1927.7 (3)C1'—C2'—C3'—C19'25.1 (3)
C20—C2—C3—C489.5 (4)C20'—C2'—C3'—C4'88.7 (4)
C1—C2—C3—C489.3 (3)C1'—C2'—C3'—C4'91.4 (3)
C2—C3—C4—C590.3 (3)C2'—C3'—C4'—C5'86.9 (3)
C19—C3—C4—C523.2 (4)C19'—C3'—C4'—C5'25.9 (3)
C25—O5—C5—C486.8 (3)C25'—O5'—C5'—C4'85.7 (3)
C25—O5—C5—C6147.7 (2)C25'—O5'—C5'—C6'149.8 (2)
C3—C4—C5—O586.6 (3)C3'—C4'—C5'—O5'87.2 (3)
C3—C4—C5—C635.1 (3)C3'—C4'—C5'—C6'34.4 (3)
O5—C5—C6—C746.6 (3)O5'—C5'—C6'—C7'50.0 (3)
C4—C5—C6—C7168.5 (2)C4'—C5'—C6'—C7'172.3 (2)
O5—C5—C6—C1882.2 (3)O5'—C5'—C6'—C18'78.6 (2)
C4—C5—C6—C1839.8 (3)C4'—C5'—C6'—C18'43.6 (3)
C5—C6—C7—C1591.4 (3)C5'—C6'—C7'—C15'88.7 (3)
C18—C6—C7—C1538.7 (3)C18'—C6'—C7'—C15'41.5 (3)
C5—C6—C7—C1137.9 (3)C5'—C6'—C7'—C8'149.8 (2)
C18—C6—C7—C11168.0 (2)C18'—C6'—C7'—C8'80.1 (2)
C5—C6—C7—C8148.2 (2)C5'—C6'—C7'—C11'39.5 (3)
C18—C6—C7—C881.7 (3)C18'—C6'—C7'—C11'169.7 (2)
C10—O9—C8—C718.5 (4)C10'—O9'—C8'—C7'16.8 (3)
C15—C7—C8—O9153.9 (2)C15'—C7'—C8'—O9'153.0 (2)
C11—C7—C8—O930.6 (3)C6'—C7'—C8'—O9'87.9 (3)
C6—C7—C8—O988.2 (3)C11'—C7'—C8'—O9'30.7 (3)
C8—O9—C10—O7178.0 (3)C8'—O9'—C10'—O7'175.5 (3)
C8—O9—C10—C112.5 (4)C8'—O9'—C10'—C11'5.4 (3)
O7—C10—C11—C7158.4 (3)O7'—C10'—C11'—C7'156.2 (3)
O9—C10—C11—C722.2 (3)O9'—C10'—C11'—C7'24.7 (3)
O7—C10—C11—C1276.8 (4)O7'—C10'—C11'—C12'78.5 (4)
O9—C10—C11—C12102.5 (3)O9'—C10'—C11'—C12'100.6 (3)
C15—C7—C11—C10151.0 (2)C15'—C7'—C11'—C10'153.1 (2)
C8—C7—C11—C1030.7 (3)C8'—C7'—C11'—C10'32.3 (3)
C6—C7—C11—C1083.9 (3)C6'—C7'—C11'—C10'82.0 (3)
C15—C7—C11—C1231.0 (4)C15'—C7'—C11'—C12'33.1 (4)
C8—C7—C11—C1289.3 (3)C8'—C7'—C11'—C12'87.8 (3)
C6—C7—C11—C12156.1 (3)C6'—C7'—C11'—C12'158.0 (2)
C10—C11—C12—C2287.7 (4)C10'—C11'—C12'—C21'31.6 (3)
C7—C11—C12—C22156.8 (3)C7'—C11'—C12'—C21'83.9 (3)
C10—C11—C12—C13154.9 (3)C10'—C11'—C12'—C13'154.9 (3)
C7—C11—C12—C1339.3 (4)C7'—C11'—C12'—C13'39.4 (4)
C10—C11—C12—C2131.9 (4)C10'—C11'—C12'—C22'87.1 (4)
C7—C11—C12—C2183.6 (3)C7'—C11'—C12'—C22'157.4 (3)
C22—C12—C13—C14173.6 (3)C21'—C12'—C13'—C14'70.3 (3)
C21—C12—C13—C1467.9 (4)C22'—C12'—C13'—C14'172.6 (3)
C11—C12—C13—C1457.0 (4)C11'—C12'—C13'—C14'55.6 (4)
C12—C13—C14—C1566.1 (4)C12'—C13'—C14'—C15'64.5 (3)
C17—O16—C15—C14178.3 (3)C17'—O16'—C15'—C14'175.7 (2)
C17—O16—C15—C754.2 (3)C17'—O16'—C15'—C7'51.4 (3)
C13—C14—C15—O16173.9 (3)C13'—C14'—C15'—O16'175.6 (2)
C13—C14—C15—C754.9 (4)C13'—C14'—C15'—C7'55.7 (3)
C11—C7—C15—O16159.0 (2)C8'—C7'—C15'—O16'46.7 (3)
C8—C7—C15—O1644.8 (3)C6'—C7'—C15'—O16'71.7 (3)
C6—C7—C15—O1673.1 (3)C11'—C7'—C15'—O16'161.0 (2)
C11—C7—C15—C1438.7 (4)C8'—C7'—C15'—C14'73.4 (3)
C8—C7—C15—C1475.4 (4)C6'—C7'—C15'—C14'168.2 (2)
C6—C7—C15—C14166.6 (3)C11'—C7'—C15'—C14'40.9 (3)
C15—O16—C17—O1178.6 (3)C15'—O16'—C17'—O1'177.6 (3)
C15—O16—C17—C181.3 (4)C15'—O16'—C17'—C18'1.7 (4)
O1—C17—C18—C127.7 (4)O1'—C17'—C18'—C1'33.1 (4)
O16—C17—C18—C1152.4 (3)O16'—C17'—C18'—C1'147.7 (2)
O1—C17—C18—C1985.3 (4)O1'—C17'—C18'—C19'78.5 (4)
O16—C17—C18—C1994.5 (3)O16'—C17'—C18'—C19'100.7 (3)
O1—C17—C18—C6147.3 (3)O1'—C17'—C18'—C6'153.2 (3)
O16—C17—C18—C632.8 (4)O16'—C17'—C18'—C6'27.6 (4)
O2—C1—C18—C1737.0 (4)O2'—C1'—C18'—C17'31.9 (4)
C2—C1—C18—C17146.9 (2)C2'—C1'—C18'—C17'149.8 (2)
O2—C1—C18—C19157.7 (3)O2'—C1'—C18'—C19'151.5 (3)
C2—C1—C18—C1926.1 (3)C2'—C1'—C18'—C19'30.2 (2)
O2—C1—C18—C688.8 (4)O2'—C1'—C18'—C6'94.8 (3)
C2—C1—C18—C687.3 (3)C2'—C1'—C18'—C6'83.5 (2)
C5—C6—C18—C17142.9 (2)C5'—C6'—C18'—C17'137.0 (2)
C7—C6—C18—C1710.6 (3)C7'—C6'—C18'—C17'4.8 (3)
C5—C6—C18—C194.8 (3)C5'—C6'—C18'—C1'99.7 (2)
C7—C6—C18—C1133.0 (3)C7'—C6'—C18'—C1'128.0 (2)
C5—C6—C18—C1913.2 (3)C5'—C6'—C18'—C19'7.0 (3)
C7—C6—C18—C19119.0 (2)C7'—C6'—C18'—C19'125.2 (2)
C23—O3—C19—C3163.9 (2)C23'—O3'—C19'—C3'161.0 (2)
C23—O3—C19—C1887.2 (3)C23'—O3'—C19'—C18'90.1 (3)
C2—C3—C19—O372.1 (3)C2'—C3'—C19'—O3'70.4 (2)
C4—C3—C19—O3169.6 (2)C4'—C3'—C19'—O3'170.2 (2)
C2—C3—C19—C1843.4 (3)C2'—C3'—C19'—C18'43.8 (2)
C4—C3—C19—C1874.9 (3)C4'—C3'—C19'—C18'75.6 (2)
C17—C18—C19—O347.8 (3)C17'—C18'—C19'—O3'50.9 (3)
C1—C18—C19—O370.6 (3)C1'—C18'—C19'—O3'67.3 (2)
C6—C18—C19—O3178.67 (19)C6'—C18'—C19'—O3'177.32 (19)
C17—C18—C19—C3160.5 (2)C17'—C18'—C19'—C3'163.5 (2)
C1—C18—C19—C342.1 (3)C1'—C18'—C19'—C3'45.3 (2)
C6—C18—C19—C368.6 (3)C6'—C18'—C19'—C3'64.7 (2)
C19—O3—C23—O44.5 (4)C19'—O3'—C23'—O4'3.2 (5)
C19—O3—C23—C24176.1 (3)C19'—O3'—C23'—C24'175.0 (3)
C5—O5—C25—O67.9 (5)C5'—O5'—C25'—O6'0.7 (4)
C5—O5—C25—C26173.8 (3)C5'—O5'—C25'—C26'177.6 (3)
 

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