
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619008817/fp3073sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008817/fp3073Isup2.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008817/fp3073IIIsup3.hkl |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619008817/fp3073sup4.pdf |
CCDC references: 1935527; 1935526
For both structures, data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2015a) for (I); SHELXT (Sheldrick, 2015a) for (III). For both structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
C16H22O11 | Dx = 1.344 Mg m−3 |
Mr = 390.33 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 9740 reflections |
a = 8.8434 (4) Å | θ = 3.6–71.7° |
b = 15.1918 (6) Å | µ = 1.00 mm−1 |
c = 43.0639 (17) Å | T = 120 K |
V = 5785.5 (4) Å3 | Needle, clear colourless |
Z = 12 | 0.17 × 0.05 × 0.02 mm |
F(000) = 2472 |
Bruker APEXII CCD diffractometer | 11335 independent reflections |
Radiation source: Incoatec micro-focus | 10694 reflections with I > 2σ(I) |
Detector resolution: 8.33 pixels mm-1 | Rint = 0.046 |
φ and ω scans | θmax = 72.0°, θmin = 2.1° |
Absorption correction: numerical (SADABS; Krause et al., 2015) | h = −10→10 |
Tmin = 0.692, Tmax = 0.939 | k = −18→18 |
78838 measured reflections | l = −52→53 |
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) = 0.110 | w = 1/[σ2(Fo2) + (0.0764P)2 + 0.596P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.030 |
11335 reflections | Δρmax = 0.45 e Å−3 |
754 parameters | Δρmin = −0.25 e Å−3 |
6 restraints | Absolute structure: Flack x determined using 4495 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.07 (4) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.9767 (2) | 0.00373 (13) | 0.86654 (5) | 0.0373 (4) | |
O2 | 0.7275 (2) | 0.16020 (14) | 0.83026 (4) | 0.0354 (4) | |
O3 | 0.9626 (2) | 0.27328 (13) | 0.84368 (4) | 0.0313 (4) | |
O4 | 0.9383 (2) | 0.26391 (12) | 0.91044 (4) | 0.0284 (3) | |
O5 | 0.7509 (2) | 0.06018 (13) | 0.88578 (4) | 0.0340 (4) | |
O6 | 0.6934 (2) | 0.05736 (13) | 0.94909 (4) | 0.0352 (4) | |
O7 | 0.8723 (3) | −0.13120 (17) | 0.87041 (7) | 0.0633 (7) | |
O8 | 0.8086 (3) | 0.16490 (18) | 0.78083 (5) | 0.0500 (5) | |
O9 | 1.1672 (2) | 0.21730 (17) | 0.81960 (5) | 0.0429 (5) | |
O10 | 0.7728 (2) | 0.37476 (12) | 0.90327 (5) | 0.0329 (4) | |
O11 | 0.5252 (2) | 0.12778 (15) | 0.97930 (4) | 0.0392 (4) | |
C1 | 0.8326 (3) | 0.0412 (2) | 0.85888 (6) | 0.0358 (6) | |
H1 | 0.774070 | −0.000980 | 0.845705 | 0.043* | |
C2 | 0.8690 (3) | 0.12350 (18) | 0.84016 (6) | 0.0319 (5) | |
H2 | 0.932930 | 0.108214 | 0.821784 | 0.038* | |
C3 | 0.9490 (3) | 0.19183 (17) | 0.86044 (5) | 0.0281 (5) | |
H3 | 1.051307 | 0.169929 | 0.866614 | 0.034* | |
C4 | 0.8535 (3) | 0.20927 (17) | 0.88918 (5) | 0.0273 (5) | |
H4 | 0.756423 | 0.238677 | 0.883313 | 0.033* | |
C5 | 0.8219 (3) | 0.12249 (17) | 0.90626 (6) | 0.0285 (5) | |
H5 | 0.918113 | 0.097548 | 0.914732 | 0.034* | |
C6 | 0.7110 (3) | 0.13890 (18) | 0.93223 (6) | 0.0311 (5) | |
H6A | 0.749400 | 0.185560 | 0.946203 | 0.037* | |
H6B | 0.612435 | 0.158116 | 0.923675 | 0.037* | |
C7 | 0.9792 (4) | −0.0839 (2) | 0.87404 (7) | 0.0448 (7) | |
C8 | 1.1298 (5) | −0.1089 (2) | 0.88671 (9) | 0.0553 (8) | |
H8A | 1.206276 | −0.103700 | 0.870352 | 0.083* | |
H8B | 1.126326 | −0.169851 | 0.894161 | 0.083* | |
H8C | 1.155867 | −0.069710 | 0.903968 | 0.083* | |
C9 | 0.7113 (3) | 0.17773 (19) | 0.79951 (6) | 0.0356 (6) | |
C10 | 0.5576 (3) | 0.2142 (2) | 0.79296 (7) | 0.0421 (6) | |
H10D | 0.487287 | 0.165803 | 0.788771 | 0.063* | |
H10E | 0.562541 | 0.253063 | 0.774821 | 0.063* | |
H10F | 0.522229 | 0.247733 | 0.811000 | 0.063* | |
C11 | 1.0754 (3) | 0.2756 (2) | 0.82214 (6) | 0.0347 (6) | |
C12 | 1.0653 (3) | 0.3563 (2) | 0.80258 (7) | 0.0444 (7) | |
H12D | 0.972912 | 0.354107 | 0.790038 | 0.067* | |
H12E | 1.153551 | 0.359463 | 0.788859 | 0.067* | |
H12F | 1.062818 | 0.408420 | 0.815980 | 0.067* | |
C13 | 0.8819 (3) | 0.34529 (16) | 0.91630 (5) | 0.0253 (4) | |
C14 | 0.9733 (3) | 0.39184 (18) | 0.94041 (6) | 0.0323 (5) | |
H14D | 0.994674 | 0.351468 | 0.957603 | 0.049* | |
H14E | 0.916508 | 0.442654 | 0.948193 | 0.049* | |
H14F | 1.068657 | 0.411945 | 0.931240 | 0.049* | |
C15 | 0.5985 (3) | 0.0631 (2) | 0.97333 (6) | 0.0354 (6) | |
C16 | 0.5976 (4) | −0.0210 (2) | 0.99180 (8) | 0.0494 (8) | |
H16D | 0.625341 | −0.070293 | 0.978270 | 0.074* | |
H16E | 0.496233 | −0.030940 | 1.000300 | 0.074* | |
H16F | 0.670598 | −0.016511 | 1.008842 | 0.074* | |
O1' | 0.5508 (2) | 0.77458 (17) | 0.86961 (5) | 0.0429 (5) | |
O2' | 0.6585 (2) | 0.70816 (13) | 0.79238 (4) | 0.0317 (4) | |
O3' | 0.5477 (2) | 0.87430 (13) | 0.77922 (4) | 0.0372 (4) | |
O4' | 0.2354 (2) | 0.85397 (12) | 0.80419 (4) | 0.0302 (4) | |
O5' | 0.4374 (2) | 0.66848 (12) | 0.83775 (4) | 0.0306 (4) | |
O6' | 0.1257 (2) | 0.62495 (14) | 0.84823 (4) | 0.0350 (4) | |
O7' | 0.6885 (4) | 0.6944 (2) | 0.90233 (6) | 0.0670 (8) | |
O8' | 0.8780 (2) | 0.77943 (16) | 0.78301 (6) | 0.0481 (5) | |
O9' | 0.5090 (12) | 1.0047 (3) | 0.80002 (15) | 0.082 (2) | 0.5 |
O9'A | 0.6386 (11) | 0.9883 (4) | 0.80298 (11) | 0.073 (2) | 0.5 |
O10' | 0.2298 (3) | 0.86657 (17) | 0.75210 (5) | 0.0488 (5) | |
O11' | −0.0852 (3) | 0.5949 (2) | 0.82206 (6) | 0.0630 (8) | |
C1' | 0.5725 (3) | 0.7125 (2) | 0.84450 (6) | 0.0355 (6) | |
H1' | 0.652303 | 0.668884 | 0.850323 | 0.043* | |
C2' | 0.6271 (3) | 0.76826 (19) | 0.81744 (6) | 0.0327 (5) | |
H2' | 0.721125 | 0.800744 | 0.823367 | 0.039* | |
C3' | 0.5046 (3) | 0.83272 (17) | 0.80802 (6) | 0.0304 (5) | |
H3' | 0.494186 | 0.878735 | 0.824488 | 0.037* | |
C4' | 0.3527 (3) | 0.78810 (16) | 0.80318 (6) | 0.0269 (5) | |
H4' | 0.350702 | 0.755904 | 0.782927 | 0.032* | |
C5' | 0.3137 (3) | 0.72593 (17) | 0.83007 (5) | 0.0276 (5) | |
H5' | 0.285480 | 0.761406 | 0.848749 | 0.033* | |
C6' | 0.1825 (3) | 0.66883 (18) | 0.82081 (6) | 0.0316 (5) | |
H6'A | 0.101785 | 0.705309 | 0.811414 | 0.038* | |
H6'B | 0.215460 | 0.624755 | 0.805295 | 0.038* | |
C7' | 0.6210 (5) | 0.7594 (3) | 0.89692 (7) | 0.0528 (9) | |
C8' | 0.5978 (6) | 0.8342 (3) | 0.91894 (8) | 0.0713 (13) | |
H8'A | 0.637414 | 0.888469 | 0.909715 | 0.107* | |
H8'B | 0.651134 | 0.822022 | 0.938413 | 0.107* | |
H8'C | 0.489496 | 0.841180 | 0.923132 | 0.107* | |
C9' | 0.7929 (3) | 0.72002 (19) | 0.77746 (6) | 0.0338 (5) | |
C10' | 0.8177 (3) | 0.6495 (2) | 0.75383 (6) | 0.0398 (6) | |
H10A | 0.785708 | 0.592713 | 0.762358 | 0.060* | |
H10B | 0.925322 | 0.646901 | 0.748445 | 0.060* | |
H10C | 0.758514 | 0.662741 | 0.735164 | 0.060* | |
C11' | 0.5809 (6) | 0.9573 (2) | 0.77935 (7) | 0.0571 (10) | |
C12' | 0.6175 (5) | 0.9932 (2) | 0.74801 (6) | 0.0468 (7) | |
H12A | 0.627887 | 0.944612 | 0.733197 | 0.070* | |
H12B | 0.712645 | 1.026173 | 0.749015 | 0.070* | |
H12C | 0.536049 | 1.032492 | 0.741211 | 0.070* | |
C13' | 0.1829 (3) | 0.88749 (18) | 0.77697 (7) | 0.0342 (5) | |
C14' | 0.0634 (4) | 0.9549 (2) | 0.78346 (8) | 0.0423 (6) | |
H14A | −0.016083 | 0.928679 | 0.796341 | 0.064* | |
H14B | 0.019614 | 0.975294 | 0.763832 | 0.064* | |
H14C | 0.108461 | 1.004920 | 0.794473 | 0.064* | |
C15' | −0.0117 (3) | 0.5882 (2) | 0.84508 (7) | 0.0408 (7) | |
C16' | −0.0578 (4) | 0.5371 (3) | 0.87305 (9) | 0.0655 (12) | |
H16A | 0.030224 | 0.527999 | 0.886493 | 0.098* | |
H16B | −0.098396 | 0.479885 | 0.866611 | 0.098* | |
H16C | −0.135631 | 0.569734 | 0.884440 | 0.098* | |
O1" | 0.50928 (19) | 0.47554 (12) | 0.86740 (4) | 0.0269 (3) | |
O2" | 0.25074 (19) | 0.56673 (11) | 0.92338 (4) | 0.0287 (3) | |
O3" | 0.4895 (2) | 0.55590 (14) | 0.96268 (4) | 0.0356 (4) | |
O4" | 0.54649 (19) | 0.37000 (13) | 0.96282 (4) | 0.0292 (4) | |
O5" | 0.31376 (19) | 0.40220 (11) | 0.89322 (4) | 0.0256 (3) | |
O6" | 0.3832 (2) | 0.21389 (12) | 0.89309 (4) | 0.0299 (4) | |
O7" | 0.3793 (3) | 0.43791 (19) | 0.82464 (5) | 0.0502 (6) | |
O8" | 0.3069 (3) | 0.71143 (15) | 0.92369 (7) | 0.0584 (7) | |
O9" | 0.7442 (3) | 0.55746 (18) | 0.96681 (6) | 0.0531 (6) | |
O10" | 0.3819 (3) | 0.3575 (2) | 1.00200 (5) | 0.0553 (7) | |
O11" | 0.2509 (3) | 0.10262 (15) | 0.91357 (5) | 0.0481 (5) | |
C1" | 0.3679 (3) | 0.48445 (16) | 0.88336 (5) | 0.0264 (5) | |
H1" | 0.292166 | 0.511928 | 0.869094 | 0.032* | |
C2" | 0.3979 (3) | 0.54644 (16) | 0.91045 (6) | 0.0273 (5) | |
H2" | 0.448361 | 0.601393 | 0.902967 | 0.033* | |
C3" | 0.4943 (3) | 0.50176 (17) | 0.93516 (5) | 0.0272 (5) | |
H3" | 0.600919 | 0.496605 | 0.927667 | 0.033* | |
C4" | 0.4337 (3) | 0.41107 (17) | 0.94344 (5) | 0.0260 (5) | |
H4" | 0.335371 | 0.416076 | 0.954773 | 0.031* | |
C5" | 0.4147 (3) | 0.35635 (16) | 0.91387 (5) | 0.0251 (5) | |
H5" | 0.515227 | 0.348809 | 0.903582 | 0.030* | |
C6" | 0.3453 (3) | 0.26701 (16) | 0.91980 (5) | 0.0272 (5) | |
H6"A | 0.387263 | 0.240685 | 0.938984 | 0.033* | |
H6"B | 0.234173 | 0.271960 | 0.922067 | 0.033* | |
C7" | 0.4974 (3) | 0.44895 (19) | 0.83724 (6) | 0.0335 (5) | |
C8" | 0.6514 (3) | 0.4363 (2) | 0.82323 (6) | 0.0405 (6) | |
H8"A | 0.703663 | 0.493094 | 0.822193 | 0.061* | |
H8"B | 0.641003 | 0.412030 | 0.802253 | 0.061* | |
H8"C | 0.709991 | 0.395486 | 0.836109 | 0.061* | |
C9" | 0.2192 (3) | 0.65288 (18) | 0.92846 (7) | 0.0350 (6) | |
C10" | 0.0619 (4) | 0.6648 (2) | 0.94069 (8) | 0.0451 (7) | |
H10G | 0.013454 | 0.607150 | 0.942986 | 0.068* | |
H10H | 0.003376 | 0.700874 | 0.926148 | 0.068* | |
H10I | 0.065997 | 0.694173 | 0.960934 | 0.068* | |
C11" | 0.6224 (4) | 0.5788 (2) | 0.97605 (8) | 0.0480 (7) | |
C12" | 0.5907 (6) | 0.6325 (5) | 1.00451 (14) | 0.106 (2) | |
H12G | 0.522923 | 0.681246 | 0.999159 | 0.159* | |
H12H | 0.685796 | 0.656105 | 1.012710 | 0.159* | |
H12I | 0.542662 | 0.595313 | 1.020267 | 0.159* | |
C13" | 0.5084 (3) | 0.35107 (18) | 0.99243 (6) | 0.0310 (5) | |
C14" | 0.6434 (3) | 0.3206 (2) | 1.01054 (6) | 0.0372 (6) | |
H14G | 0.670201 | 0.260669 | 1.004141 | 0.056* | |
H14H | 0.619403 | 0.321026 | 1.032756 | 0.056* | |
H14I | 0.728795 | 0.360100 | 1.006558 | 0.056* | |
C15" | 0.3287 (3) | 0.13076 (18) | 0.89315 (6) | 0.0313 (5) | |
C16" | 0.3787 (3) | 0.08173 (19) | 0.86474 (7) | 0.0376 (6) | |
H16G | 0.296177 | 0.080599 | 0.849567 | 0.056* | |
H16H | 0.405915 | 0.021315 | 0.870442 | 0.056* | |
H16I | 0.466774 | 0.111222 | 0.855648 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0384 (10) | 0.0295 (9) | 0.0440 (10) | −0.0014 (8) | 0.0122 (8) | −0.0054 (8) |
O2 | 0.0282 (9) | 0.0507 (11) | 0.0273 (9) | −0.0038 (8) | 0.0015 (7) | −0.0084 (8) |
O3 | 0.0292 (9) | 0.0381 (10) | 0.0266 (8) | −0.0031 (7) | 0.0026 (7) | −0.0001 (7) |
O4 | 0.0253 (8) | 0.0339 (9) | 0.0260 (8) | 0.0032 (7) | −0.0030 (6) | −0.0050 (7) |
O5 | 0.0298 (9) | 0.0414 (10) | 0.0307 (9) | −0.0081 (8) | 0.0067 (7) | −0.0084 (8) |
O6 | 0.0382 (10) | 0.0384 (10) | 0.0292 (9) | 0.0003 (8) | 0.0090 (7) | −0.0010 (7) |
O7 | 0.0706 (17) | 0.0417 (13) | 0.0775 (17) | −0.0180 (12) | 0.0127 (14) | −0.0039 (12) |
O8 | 0.0511 (12) | 0.0631 (14) | 0.0359 (10) | 0.0032 (11) | 0.0144 (10) | 0.0094 (10) |
O9 | 0.0314 (10) | 0.0617 (13) | 0.0357 (10) | −0.0003 (9) | 0.0081 (8) | −0.0013 (9) |
O10 | 0.0248 (8) | 0.0341 (9) | 0.0399 (10) | 0.0010 (7) | −0.0028 (7) | 0.0010 (7) |
O11 | 0.0344 (10) | 0.0509 (12) | 0.0323 (9) | 0.0028 (9) | 0.0085 (8) | −0.0026 (8) |
C1 | 0.0346 (13) | 0.0409 (14) | 0.0318 (13) | −0.0078 (11) | 0.0071 (10) | −0.0103 (11) |
C2 | 0.0267 (11) | 0.0417 (14) | 0.0272 (11) | −0.0029 (10) | 0.0043 (9) | −0.0079 (10) |
C3 | 0.0250 (11) | 0.0340 (12) | 0.0252 (10) | −0.0008 (9) | 0.0021 (9) | −0.0048 (9) |
C4 | 0.0244 (11) | 0.0349 (12) | 0.0225 (10) | −0.0004 (9) | −0.0002 (8) | −0.0047 (9) |
C5 | 0.0246 (11) | 0.0338 (12) | 0.0270 (11) | −0.0003 (9) | 0.0013 (9) | −0.0044 (9) |
C6 | 0.0292 (12) | 0.0373 (13) | 0.0270 (11) | 0.0041 (10) | 0.0049 (9) | 0.0001 (10) |
C7 | 0.0559 (18) | 0.0343 (14) | 0.0442 (16) | −0.0040 (13) | 0.0194 (14) | −0.0048 (12) |
C8 | 0.065 (2) | 0.0384 (16) | 0.063 (2) | 0.0113 (15) | 0.0145 (17) | 0.0056 (14) |
C9 | 0.0402 (14) | 0.0365 (13) | 0.0301 (12) | −0.0117 (11) | 0.0049 (11) | −0.0029 (10) |
C10 | 0.0399 (15) | 0.0477 (16) | 0.0389 (14) | −0.0107 (13) | −0.0049 (11) | −0.0005 (12) |
C11 | 0.0278 (12) | 0.0500 (16) | 0.0265 (11) | −0.0085 (11) | −0.0007 (9) | −0.0033 (11) |
C12 | 0.0369 (14) | 0.0595 (19) | 0.0367 (14) | −0.0118 (13) | −0.0005 (11) | 0.0093 (13) |
C13 | 0.0220 (10) | 0.0310 (12) | 0.0228 (10) | −0.0007 (9) | 0.0039 (8) | 0.0021 (8) |
C14 | 0.0319 (12) | 0.0347 (13) | 0.0305 (12) | 0.0004 (10) | −0.0030 (10) | −0.0030 (10) |
C15 | 0.0332 (13) | 0.0439 (15) | 0.0289 (12) | −0.0084 (11) | 0.0029 (10) | −0.0033 (11) |
C16 | 0.061 (2) | 0.0432 (17) | 0.0437 (16) | −0.0075 (14) | 0.0148 (15) | 0.0015 (13) |
O1' | 0.0362 (10) | 0.0635 (14) | 0.0290 (9) | −0.0090 (10) | 0.0000 (8) | −0.0081 (9) |
O2' | 0.0252 (8) | 0.0383 (10) | 0.0318 (9) | −0.0027 (7) | 0.0029 (7) | −0.0037 (7) |
O3' | 0.0470 (11) | 0.0334 (9) | 0.0312 (9) | −0.0094 (8) | 0.0154 (8) | −0.0059 (8) |
O4' | 0.0308 (8) | 0.0286 (8) | 0.0312 (9) | 0.0022 (7) | 0.0074 (7) | 0.0004 (7) |
O5' | 0.0245 (8) | 0.0347 (9) | 0.0325 (9) | −0.0004 (7) | −0.0011 (7) | 0.0032 (7) |
O6' | 0.0248 (8) | 0.0439 (10) | 0.0363 (9) | −0.0062 (8) | −0.0043 (7) | 0.0137 (8) |
O7' | 0.0810 (19) | 0.0656 (18) | 0.0544 (15) | −0.0216 (15) | −0.0280 (14) | 0.0111 (13) |
O8' | 0.0376 (11) | 0.0500 (12) | 0.0568 (13) | −0.0117 (10) | 0.0170 (10) | −0.0063 (10) |
O9' | 0.166 (8) | 0.025 (2) | 0.053 (3) | −0.013 (4) | 0.050 (4) | −0.007 (2) |
O9'A | 0.144 (6) | 0.050 (3) | 0.023 (2) | −0.054 (4) | −0.008 (3) | 0.0031 (19) |
O10' | 0.0587 (13) | 0.0562 (13) | 0.0316 (10) | 0.0180 (11) | 0.0070 (9) | 0.0089 (9) |
O11' | 0.0481 (13) | 0.0875 (19) | 0.0533 (13) | −0.0363 (13) | −0.0227 (11) | 0.0363 (13) |
C1' | 0.0250 (12) | 0.0505 (16) | 0.0310 (12) | −0.0047 (11) | −0.0014 (9) | 0.0008 (11) |
C2' | 0.0271 (11) | 0.0407 (14) | 0.0303 (12) | −0.0072 (10) | 0.0027 (10) | −0.0069 (10) |
C3' | 0.0325 (12) | 0.0318 (12) | 0.0271 (11) | −0.0073 (10) | 0.0070 (9) | −0.0035 (9) |
C4' | 0.0258 (11) | 0.0266 (11) | 0.0283 (11) | −0.0006 (9) | 0.0025 (9) | −0.0010 (9) |
C5' | 0.0233 (10) | 0.0310 (12) | 0.0285 (11) | −0.0008 (9) | 0.0006 (9) | 0.0020 (9) |
C6' | 0.0288 (12) | 0.0361 (13) | 0.0297 (12) | −0.0051 (10) | −0.0032 (10) | 0.0066 (10) |
C7' | 0.061 (2) | 0.063 (2) | 0.0344 (15) | −0.0304 (18) | −0.0099 (14) | 0.0079 (14) |
C8' | 0.086 (3) | 0.093 (3) | 0.0351 (16) | −0.047 (3) | −0.0007 (18) | −0.0128 (18) |
C9' | 0.0287 (12) | 0.0402 (14) | 0.0325 (12) | 0.0023 (11) | 0.0025 (10) | 0.0044 (11) |
C10' | 0.0362 (13) | 0.0508 (16) | 0.0324 (13) | 0.0057 (12) | 0.0031 (11) | −0.0015 (12) |
C11' | 0.109 (3) | 0.0355 (15) | 0.0266 (13) | −0.0179 (18) | 0.0029 (16) | −0.0024 (12) |
C12' | 0.071 (2) | 0.0417 (15) | 0.0272 (13) | −0.0109 (15) | 0.0044 (13) | −0.0010 (11) |
C13' | 0.0355 (13) | 0.0302 (12) | 0.0369 (14) | 0.0009 (10) | 0.0056 (11) | 0.0061 (10) |
C14' | 0.0432 (15) | 0.0327 (13) | 0.0512 (17) | 0.0071 (12) | 0.0077 (13) | 0.0085 (12) |
C15' | 0.0303 (13) | 0.0478 (16) | 0.0443 (15) | −0.0107 (12) | −0.0085 (12) | 0.0172 (13) |
C16' | 0.0458 (18) | 0.100 (3) | 0.0510 (19) | −0.035 (2) | −0.0163 (15) | 0.038 (2) |
O1" | 0.0242 (8) | 0.0342 (9) | 0.0222 (8) | −0.0027 (6) | −0.0022 (6) | 0.0036 (6) |
O2" | 0.0241 (8) | 0.0276 (8) | 0.0344 (8) | 0.0023 (7) | 0.0009 (7) | 0.0026 (7) |
O3" | 0.0316 (9) | 0.0426 (10) | 0.0325 (9) | 0.0048 (8) | −0.0045 (7) | −0.0118 (8) |
O4" | 0.0233 (8) | 0.0413 (10) | 0.0230 (8) | 0.0039 (7) | −0.0011 (6) | 0.0045 (7) |
O5" | 0.0224 (7) | 0.0299 (8) | 0.0246 (8) | −0.0024 (6) | −0.0042 (6) | 0.0033 (6) |
O6" | 0.0304 (8) | 0.0306 (9) | 0.0287 (8) | −0.0025 (7) | 0.0033 (7) | 0.0003 (7) |
O7" | 0.0399 (11) | 0.0844 (17) | 0.0264 (9) | −0.0170 (12) | −0.0060 (8) | −0.0035 (10) |
O8" | 0.0451 (12) | 0.0293 (10) | 0.101 (2) | −0.0015 (9) | 0.0163 (13) | −0.0031 (12) |
O9" | 0.0357 (11) | 0.0617 (14) | 0.0619 (14) | 0.0011 (10) | −0.0137 (10) | −0.0217 (12) |
O10" | 0.0381 (11) | 0.094 (2) | 0.0340 (10) | 0.0128 (12) | 0.0083 (9) | 0.0176 (11) |
O11" | 0.0595 (14) | 0.0405 (11) | 0.0443 (11) | −0.0166 (10) | 0.0164 (10) | −0.0042 (9) |
C1" | 0.0218 (10) | 0.0315 (12) | 0.0259 (11) | −0.0007 (9) | −0.0018 (9) | 0.0038 (9) |
C2" | 0.0230 (11) | 0.0281 (11) | 0.0308 (11) | 0.0000 (9) | 0.0003 (9) | 0.0025 (9) |
C3" | 0.0247 (11) | 0.0322 (12) | 0.0246 (11) | 0.0000 (9) | −0.0022 (9) | −0.0042 (9) |
C4" | 0.0210 (10) | 0.0340 (12) | 0.0231 (10) | 0.0024 (9) | −0.0011 (8) | 0.0033 (9) |
C5" | 0.0203 (10) | 0.0314 (12) | 0.0236 (10) | 0.0006 (8) | −0.0009 (8) | 0.0035 (9) |
C6" | 0.0257 (11) | 0.0294 (12) | 0.0266 (11) | 0.0015 (9) | 0.0025 (9) | 0.0021 (9) |
C7" | 0.0349 (13) | 0.0423 (14) | 0.0234 (11) | −0.0101 (11) | −0.0011 (10) | 0.0034 (10) |
C8" | 0.0364 (15) | 0.0563 (17) | 0.0289 (12) | −0.0117 (12) | 0.0048 (11) | −0.0050 (12) |
C9" | 0.0331 (13) | 0.0292 (12) | 0.0428 (14) | 0.0020 (10) | −0.0001 (10) | 0.0021 (10) |
C10" | 0.0387 (15) | 0.0365 (14) | 0.0600 (19) | 0.0075 (12) | 0.0087 (13) | −0.0014 (13) |
C11" | 0.0409 (16) | 0.0539 (18) | 0.0493 (17) | 0.0037 (14) | −0.0125 (14) | −0.0195 (14) |
C12" | 0.073 (3) | 0.144 (5) | 0.101 (4) | 0.017 (3) | −0.026 (3) | −0.089 (4) |
C13" | 0.0319 (12) | 0.0366 (13) | 0.0246 (11) | 0.0000 (10) | −0.0025 (9) | 0.0016 (9) |
C14" | 0.0399 (15) | 0.0443 (15) | 0.0274 (12) | −0.0005 (12) | −0.0099 (11) | 0.0042 (10) |
C15" | 0.0283 (12) | 0.0322 (12) | 0.0334 (12) | −0.0021 (10) | −0.0011 (10) | 0.0010 (10) |
C16" | 0.0361 (13) | 0.0382 (14) | 0.0385 (14) | −0.0054 (11) | 0.0050 (11) | −0.0073 (11) |
O1—C7 | 1.370 (4) | C4'—H4' | 1.0000 |
O1—C1 | 1.435 (4) | C5'—C6' | 1.503 (3) |
O2—C9 | 1.358 (3) | C5'—H5' | 1.0000 |
O2—C2 | 1.435 (3) | C6'—H6'A | 0.9900 |
O3—C11 | 1.363 (3) | C6'—H6'B | 0.9900 |
O3—C3 | 1.438 (3) | C7'—C8' | 1.494 (6) |
O4—C13 | 1.357 (3) | C8'—H8'A | 0.9800 |
O4—C4 | 1.446 (3) | C8'—H8'B | 0.9800 |
O5—C1 | 1.395 (3) | C8'—H8'C | 0.9800 |
O5—C5 | 1.438 (3) | C9'—C10' | 1.494 (4) |
O6—C15 | 1.342 (3) | C10'—H10A | 0.9800 |
O6—C6 | 1.444 (3) | C10'—H10B | 0.9800 |
O7—C7 | 1.198 (4) | C10'—H10C | 0.9800 |
O8—C9 | 1.194 (4) | C11'—C12' | 1.492 (4) |
O9—C11 | 1.206 (4) | C12'—H12A | 0.9800 |
O10—C13 | 1.202 (3) | C12'—H12B | 0.9800 |
O11—C15 | 1.205 (4) | C12'—H12C | 0.9800 |
C1—C2 | 1.522 (4) | C13'—C14' | 1.498 (4) |
C1—H1 | 1.0000 | C14'—H14A | 0.9800 |
C2—C3 | 1.530 (3) | C14'—H14B | 0.9800 |
C2—H2 | 1.0000 | C14'—H14C | 0.9800 |
C3—C4 | 1.521 (3) | C15'—C16' | 1.490 (4) |
C3—H3 | 1.0000 | C16'—H16A | 0.9800 |
C4—C5 | 1.535 (4) | C16'—H16B | 0.9800 |
C4—H4 | 1.0000 | C16'—H16C | 0.9800 |
C5—C6 | 1.508 (3) | O1"—C7" | 1.364 (3) |
C5—H5 | 1.0000 | O1"—C1" | 1.433 (3) |
C6—H6A | 0.9900 | O2"—C9" | 1.356 (3) |
C6—H6B | 0.9900 | O2"—C2" | 1.449 (3) |
C7—C8 | 1.488 (5) | O3"—C11" | 1.354 (4) |
C8—H8A | 0.9800 | O3"—C3" | 1.443 (3) |
C8—H8B | 0.9800 | O4"—C13" | 1.350 (3) |
C8—H8C | 0.9800 | O4"—C4" | 1.442 (3) |
C9—C10 | 1.494 (4) | O5"—C1" | 1.404 (3) |
C10—H10D | 0.9800 | O5"—C5" | 1.439 (3) |
C10—H10E | 0.9800 | O6"—C15" | 1.352 (3) |
C10—H10F | 0.9800 | O6"—C6" | 1.445 (3) |
C11—C12 | 1.491 (4) | O7"—C7" | 1.188 (4) |
C12—H12D | 0.9800 | O8"—C9" | 1.198 (4) |
C12—H12E | 0.9800 | O9"—C11" | 1.193 (4) |
C12—H12F | 0.9800 | O10"—C13" | 1.196 (4) |
C13—C14 | 1.494 (3) | O11"—C15" | 1.196 (4) |
C14—H14D | 0.9800 | C1"—C2" | 1.523 (3) |
C14—H14E | 0.9800 | C1"—H1" | 1.0000 |
C14—H14F | 0.9800 | C2"—C3" | 1.523 (3) |
C15—C16 | 1.505 (4) | C2"—H2" | 1.0000 |
C16—H16D | 0.9800 | C3"—C4" | 1.520 (3) |
C16—H16E | 0.9800 | C3"—H3" | 1.0000 |
C16—H16F | 0.9800 | C4"—C5" | 1.530 (3) |
O1'—C7' | 1.349 (4) | C4"—H4" | 1.0000 |
O1'—C1' | 1.448 (3) | C5"—C6" | 1.512 (3) |
O2'—C9' | 1.363 (3) | C5"—H5" | 1.0000 |
O2'—C2' | 1.441 (3) | C6"—H6"A | 0.9900 |
O3'—C11' | 1.294 (4) | C6"—H6"B | 0.9900 |
O3'—C3' | 1.443 (3) | C7"—C8" | 1.502 (4) |
O4'—C13' | 1.360 (3) | C8"—H8"A | 0.9800 |
O4'—C4' | 1.442 (3) | C8"—H8"B | 0.9800 |
O5'—C1' | 1.399 (3) | C8"—H8"C | 0.9800 |
O5'—C5' | 1.438 (3) | C9"—C10" | 1.499 (4) |
O6'—C15' | 1.344 (3) | C10"—H10G | 0.9800 |
O6'—C6' | 1.446 (3) | C10"—H10H | 0.9800 |
O7'—C7' | 1.178 (5) | C10"—H10I | 0.9800 |
O8'—C9' | 1.199 (4) | C11"—C12" | 1.499 (5) |
O9'—C11' | 1.310 (7) | C12"—H12G | 0.9800 |
O9'A—C11' | 1.232 (6) | C12"—H12H | 0.9800 |
O10'—C13' | 1.192 (4) | C12"—H12I | 0.9800 |
O11'—C15' | 1.190 (4) | C13"—C14" | 1.499 (3) |
C1'—C2' | 1.519 (4) | C14"—H14G | 0.9800 |
C1'—H1' | 1.0000 | C14"—H14H | 0.9800 |
C2'—C3' | 1.516 (4) | C14"—H14I | 0.9800 |
C2'—H2' | 1.0000 | C15"—C16" | 1.499 (4) |
C3'—C4' | 1.519 (3) | C16"—H16G | 0.9800 |
C3'—H3' | 1.0000 | C16"—H16H | 0.9800 |
C4'—C5' | 1.534 (3) | C16"—H16I | 0.9800 |
C7—O1—C1 | 117.0 (2) | C7'—C8'—H8'A | 109.5 |
C9—O2—C2 | 117.3 (2) | C7'—C8'—H8'B | 109.5 |
C11—O3—C3 | 115.1 (2) | H8'A—C8'—H8'B | 109.5 |
C13—O4—C4 | 116.72 (19) | C7'—C8'—H8'C | 109.5 |
C1—O5—C5 | 114.78 (19) | H8'A—C8'—H8'C | 109.5 |
C15—O6—C6 | 113.7 (2) | H8'B—C8'—H8'C | 109.5 |
O5—C1—O1 | 110.5 (2) | O8'—C9'—O2' | 123.6 (3) |
O5—C1—C2 | 112.3 (2) | O8'—C9'—C10' | 125.6 (3) |
O1—C1—C2 | 105.0 (2) | O2'—C9'—C10' | 110.8 (2) |
O5—C1—H1 | 109.6 | C9'—C10'—H10A | 109.5 |
O1—C1—H1 | 109.6 | C9'—C10'—H10B | 109.5 |
C2—C1—H1 | 109.6 | H10A—C10'—H10B | 109.5 |
O2—C2—C1 | 107.0 (2) | C9'—C10'—H10C | 109.5 |
O2—C2—C3 | 108.0 (2) | H10A—C10'—H10C | 109.5 |
C1—C2—C3 | 110.7 (2) | H10B—C10'—H10C | 109.5 |
O2—C2—H2 | 110.4 | O9'A—C11'—O3' | 118.0 (4) |
C1—C2—H2 | 110.4 | O3'—C11'—O9' | 115.4 (4) |
C3—C2—H2 | 110.4 | O9'A—C11'—C12' | 121.1 (4) |
O3—C3—C4 | 107.8 (2) | O3'—C11'—C12' | 113.7 (3) |
O3—C3—C2 | 109.6 (2) | O9'—C11'—C12' | 121.3 (4) |
C4—C3—C2 | 109.0 (2) | C11'—C12'—H12A | 109.5 |
O3—C3—H3 | 110.1 | C11'—C12'—H12B | 109.5 |
C4—C3—H3 | 110.1 | H12A—C12'—H12B | 109.5 |
C2—C3—H3 | 110.1 | C11'—C12'—H12C | 109.5 |
O4—C4—C3 | 109.08 (19) | H12A—C12'—H12C | 109.5 |
O4—C4—C5 | 106.48 (19) | H12B—C12'—H12C | 109.5 |
C3—C4—C5 | 109.9 (2) | O10'—C13'—O4' | 123.8 (3) |
O4—C4—H4 | 110.4 | O10'—C13'—C14' | 126.6 (3) |
C3—C4—H4 | 110.4 | O4'—C13'—C14' | 109.6 (2) |
C5—C4—H4 | 110.4 | C13'—C14'—H14A | 109.5 |
O5—C5—C6 | 106.2 (2) | C13'—C14'—H14B | 109.5 |
O5—C5—C4 | 110.5 (2) | H14A—C14'—H14B | 109.5 |
C6—C5—C4 | 109.4 (2) | C13'—C14'—H14C | 109.5 |
O5—C5—H5 | 110.2 | H14A—C14'—H14C | 109.5 |
C6—C5—H5 | 110.2 | H14B—C14'—H14C | 109.5 |
C4—C5—H5 | 110.2 | O11'—C15'—O6' | 122.8 (3) |
O6—C6—C5 | 107.5 (2) | O11'—C15'—C16' | 124.7 (3) |
O6—C6—H6A | 110.2 | O6'—C15'—C16' | 112.5 (2) |
C5—C6—H6A | 110.2 | C15'—C16'—H16A | 109.5 |
O6—C6—H6B | 110.2 | C15'—C16'—H16B | 109.5 |
C5—C6—H6B | 110.2 | H16A—C16'—H16B | 109.5 |
H6A—C6—H6B | 108.5 | C15'—C16'—H16C | 109.5 |
O7—C7—O1 | 122.6 (4) | H16A—C16'—H16C | 109.5 |
O7—C7—C8 | 126.9 (3) | H16B—C16'—H16C | 109.5 |
O1—C7—C8 | 110.4 (3) | C7"—O1"—C1" | 114.65 (19) |
C7—C8—H8A | 109.5 | C9"—O2"—C2" | 116.9 (2) |
C7—C8—H8B | 109.5 | C11"—O3"—C3" | 118.1 (2) |
H8A—C8—H8B | 109.5 | C13"—O4"—C4" | 117.79 (19) |
C7—C8—H8C | 109.5 | C1"—O5"—C5" | 113.96 (18) |
H8A—C8—H8C | 109.5 | C15"—O6"—C6" | 115.95 (19) |
H8B—C8—H8C | 109.5 | O5"—C1"—O1" | 111.01 (19) |
O8—C9—O2 | 123.3 (3) | O5"—C1"—C2" | 112.22 (19) |
O8—C9—C10 | 126.1 (3) | O1"—C1"—C2" | 105.89 (19) |
O2—C9—C10 | 110.7 (2) | O5"—C1"—H1" | 109.2 |
C9—C10—H10D | 109.5 | O1"—C1"—H1" | 109.2 |
C9—C10—H10E | 109.5 | C2"—C1"—H1" | 109.2 |
H10D—C10—H10E | 109.5 | O2"—C2"—C1" | 105.65 (19) |
C9—C10—H10F | 109.5 | O2"—C2"—C3" | 109.19 (19) |
H10D—C10—H10F | 109.5 | C1"—C2"—C3" | 110.9 (2) |
H10E—C10—H10F | 109.5 | O2"—C2"—H2" | 110.3 |
O9—C11—O3 | 122.4 (3) | C1"—C2"—H2" | 110.3 |
O9—C11—C12 | 126.4 (3) | C3"—C2"—H2" | 110.3 |
O3—C11—C12 | 111.2 (3) | O3"—C3"—C4" | 108.3 (2) |
C11—C12—H12D | 109.5 | O3"—C3"—C2" | 107.7 (2) |
C11—C12—H12E | 109.5 | C4"—C3"—C2" | 111.74 (19) |
H12D—C12—H12E | 109.5 | O3"—C3"—H3" | 109.7 |
C11—C12—H12F | 109.5 | C4"—C3"—H3" | 109.7 |
H12D—C12—H12F | 109.5 | C2"—C3"—H3" | 109.7 |
H12E—C12—H12F | 109.5 | O4"—C4"—C3" | 106.50 (19) |
O10—C13—O4 | 123.2 (2) | O4"—C4"—C5" | 108.81 (19) |
O10—C13—C14 | 125.6 (2) | C3"—C4"—C5" | 109.63 (19) |
O4—C13—C14 | 111.2 (2) | O4"—C4"—H4" | 110.6 |
C13—C14—H14D | 109.5 | C3"—C4"—H4" | 110.6 |
C13—C14—H14E | 109.5 | C5"—C4"—H4" | 110.6 |
H14D—C14—H14E | 109.5 | O5"—C5"—C6" | 106.69 (19) |
C13—C14—H14F | 109.5 | O5"—C5"—C4" | 108.63 (19) |
H14D—C14—H14F | 109.5 | C6"—C5"—C4" | 113.06 (19) |
H14E—C14—H14F | 109.5 | O5"—C5"—H5" | 109.5 |
O11—C15—O6 | 123.8 (3) | C6"—C5"—H5" | 109.5 |
O11—C15—C16 | 125.2 (3) | C4"—C5"—H5" | 109.5 |
O6—C15—C16 | 111.0 (3) | O6"—C6"—C5" | 105.81 (18) |
C15—C16—H16D | 109.5 | O6"—C6"—H6"A | 110.6 |
C15—C16—H16E | 109.5 | C5"—C6"—H6"A | 110.6 |
H16D—C16—H16E | 109.5 | O6"—C6"—H6"B | 110.6 |
C15—C16—H16F | 109.5 | C5"—C6"—H6"B | 110.6 |
H16D—C16—H16F | 109.5 | H6"A—C6"—H6"B | 108.7 |
H16E—C16—H16F | 109.5 | O7"—C7"—O1" | 123.0 (3) |
C7'—O1'—C1' | 118.6 (3) | O7"—C7"—C8" | 126.5 (2) |
C9'—O2'—C2' | 115.9 (2) | O1"—C7"—C8" | 110.5 (2) |
C11'—O3'—C3' | 118.9 (2) | C7"—C8"—H8"A | 109.5 |
C13'—O4'—C4' | 118.63 (19) | C7"—C8"—H8"B | 109.5 |
C1'—O5'—C5' | 114.0 (2) | H8"A—C8"—H8"B | 109.5 |
C15'—O6'—C6' | 115.0 (2) | C7"—C8"—H8"C | 109.5 |
O5'—C1'—O1' | 110.7 (2) | H8"A—C8"—H8"C | 109.5 |
O5'—C1'—C2' | 112.2 (2) | H8"B—C8"—H8"C | 109.5 |
O1'—C1'—C2' | 104.6 (2) | O8"—C9"—O2" | 123.8 (3) |
O5'—C1'—H1' | 109.7 | O8"—C9"—C10" | 124.8 (3) |
O1'—C1'—H1' | 109.7 | O2"—C9"—C10" | 111.4 (2) |
C2'—C1'—H1' | 109.7 | C9"—C10"—H10G | 109.5 |
O2'—C2'—C3' | 110.3 (2) | C9"—C10"—H10H | 109.5 |
O2'—C2'—C1' | 106.4 (2) | H10G—C10"—H10H | 109.5 |
C3'—C2'—C1' | 109.8 (2) | C9"—C10"—H10I | 109.5 |
O2'—C2'—H2' | 110.1 | H10G—C10"—H10I | 109.5 |
C3'—C2'—H2' | 110.1 | H10H—C10"—H10I | 109.5 |
C1'—C2'—H2' | 110.1 | O9"—C11"—O3" | 124.9 (3) |
O3'—C3'—C2' | 108.9 (2) | O9"—C11"—C12" | 126.1 (3) |
O3'—C3'—C4' | 108.1 (2) | O3"—C11"—C12" | 109.0 (3) |
C2'—C3'—C4' | 112.4 (2) | C11"—C12"—H12G | 109.5 |
O3'—C3'—H3' | 109.1 | C11"—C12"—H12H | 109.5 |
C2'—C3'—H3' | 109.1 | H12G—C12"—H12H | 109.5 |
C4'—C3'—H3' | 109.1 | C11"—C12"—H12I | 109.5 |
O4'—C4'—C3' | 108.81 (19) | H12G—C12"—H12I | 109.5 |
O4'—C4'—C5' | 104.05 (18) | H12H—C12"—H12I | 109.5 |
C3'—C4'—C5' | 111.7 (2) | O10"—C13"—O4" | 122.8 (2) |
O4'—C4'—H4' | 110.7 | O10"—C13"—C14" | 126.2 (2) |
C3'—C4'—H4' | 110.7 | O4"—C13"—C14" | 111.0 (2) |
C5'—C4'—H4' | 110.7 | C13"—C14"—H14G | 109.5 |
O5'—C5'—C6' | 107.4 (2) | C13"—C14"—H14H | 109.5 |
O5'—C5'—C4' | 112.11 (19) | H14G—C14"—H14H | 109.5 |
C6'—C5'—C4' | 109.20 (19) | C13"—C14"—H14I | 109.5 |
O5'—C5'—H5' | 109.4 | H14G—C14"—H14I | 109.5 |
C6'—C5'—H5' | 109.4 | H14H—C14"—H14I | 109.5 |
C4'—C5'—H5' | 109.4 | O11"—C15"—O6" | 122.7 (3) |
O6'—C6'—C5' | 108.5 (2) | O11"—C15"—C16" | 126.3 (3) |
O6'—C6'—H6'A | 110.0 | O6"—C15"—C16" | 111.0 (2) |
C5'—C6'—H6'A | 110.0 | C15"—C16"—H16G | 109.5 |
O6'—C6'—H6'B | 110.0 | C15"—C16"—H16H | 109.5 |
C5'—C6'—H6'B | 110.0 | H16G—C16"—H16H | 109.5 |
H6'A—C6'—H6'B | 108.4 | C15"—C16"—H16I | 109.5 |
O7'—C7'—O1' | 123.3 (4) | H16G—C16"—H16I | 109.5 |
O7'—C7'—C8' | 125.6 (4) | H16H—C16"—H16I | 109.5 |
O1'—C7'—C8' | 111.1 (4) | ||
C5—O5—C1—O1 | 60.8 (3) | C2'—C3'—C4'—C5' | 47.5 (3) |
C5—O5—C1—C2 | −56.2 (3) | C1'—O5'—C5'—C6' | 175.1 (2) |
C7—O1—C1—O5 | 79.9 (3) | C1'—O5'—C5'—C4' | 55.2 (3) |
C7—O1—C1—C2 | −158.7 (2) | O4'—C4'—C5'—O5' | −165.49 (19) |
C9—O2—C2—C1 | −127.8 (2) | C3'—C4'—C5'—O5' | −48.3 (3) |
C9—O2—C2—C3 | 113.0 (2) | O4'—C4'—C5'—C6' | 75.7 (2) |
O5—C1—C2—O2 | −63.4 (3) | C3'—C4'—C5'—C6' | −167.1 (2) |
O1—C1—C2—O2 | 176.36 (19) | C15'—O6'—C6'—C5' | 165.1 (2) |
O5—C1—C2—C3 | 54.0 (3) | O5'—C5'—C6'—O6' | 70.8 (3) |
O1—C1—C2—C3 | −66.2 (3) | C4'—C5'—C6'—O6' | −167.5 (2) |
C11—O3—C3—C4 | 163.37 (19) | C1'—O1'—C7'—O7' | −6.8 (5) |
C11—O3—C3—C2 | −78.1 (3) | C1'—O1'—C7'—C8' | 174.5 (3) |
O2—C2—C3—O3 | −54.9 (3) | C2'—O2'—C9'—O8' | −4.5 (4) |
C1—C2—C3—O3 | −171.7 (2) | C2'—O2'—C9'—C10' | 175.4 (2) |
O2—C2—C3—C4 | 62.8 (3) | C3'—O3'—C11'—O9'A | 31.5 (8) |
C1—C2—C3—C4 | −54.0 (3) | C3'—O3'—C11'—O9' | −30.9 (7) |
C13—O4—C4—C3 | 115.8 (2) | C3'—O3'—C11'—C12' | −177.7 (3) |
C13—O4—C4—C5 | −125.6 (2) | C4'—O4'—C13'—O10' | −1.2 (4) |
O3—C3—C4—O4 | −69.2 (2) | C4'—O4'—C13'—C14' | −179.5 (2) |
C2—C3—C4—O4 | 171.9 (2) | C6'—O6'—C15'—O11' | −3.8 (5) |
O3—C3—C4—C5 | 174.35 (19) | C6'—O6'—C15'—C16' | 174.7 (3) |
C2—C3—C4—C5 | 55.4 (3) | C5"—O5"—C1"—O1" | 59.3 (2) |
C1—O5—C5—C6 | 175.7 (2) | C5"—O5"—C1"—C2" | −59.0 (3) |
C1—O5—C5—C4 | 57.1 (3) | C7"—O1"—C1"—O5" | 79.7 (2) |
O4—C4—C5—O5 | −174.18 (18) | C7"—O1"—C1"—C2" | −158.2 (2) |
C3—C4—C5—O5 | −56.1 (3) | C9"—O2"—C2"—C1" | −130.9 (2) |
O4—C4—C5—C6 | 69.2 (2) | C9"—O2"—C2"—C3" | 109.7 (2) |
C3—C4—C5—C6 | −172.7 (2) | O5"—C1"—C2"—O2" | −67.9 (2) |
C15—O6—C6—C5 | 179.1 (2) | O1"—C1"—C2"—O2" | 170.83 (18) |
O5—C5—C6—O6 | 65.0 (2) | O5"—C1"—C2"—C3" | 50.3 (3) |
C4—C5—C6—O6 | −175.72 (19) | O1"—C1"—C2"—C3" | −71.0 (2) |
C1—O1—C7—O7 | 10.2 (4) | C11"—O3"—C3"—C4" | 110.3 (3) |
C1—O1—C7—C8 | −170.0 (2) | C11"—O3"—C3"—C2" | −128.7 (3) |
C2—O2—C9—O8 | −0.8 (4) | O2"—C2"—C3"—O3" | −51.3 (3) |
C2—O2—C9—C10 | 179.2 (2) | C1"—C2"—C3"—O3" | −167.32 (19) |
C3—O3—C11—O9 | −7.6 (4) | O2"—C2"—C3"—C4" | 67.5 (2) |
C3—O3—C11—C12 | 170.9 (2) | C1"—C2"—C3"—C4" | −48.5 (3) |
C4—O4—C13—O10 | −5.0 (3) | C13"—O4"—C4"—C3" | 115.9 (2) |
C4—O4—C13—C14 | 175.5 (2) | C13"—O4"—C4"—C5" | −126.0 (2) |
C6—O6—C15—O11 | 5.4 (4) | O3"—C3"—C4"—O4" | −70.9 (2) |
C6—O6—C15—C16 | −174.1 (2) | C2"—C3"—C4"—O4" | 170.65 (18) |
C5'—O5'—C1'—O1' | 56.8 (3) | O3"—C3"—C4"—C5" | 171.52 (18) |
C5'—O5'—C1'—C2' | −59.6 (3) | C2"—C3"—C4"—C5" | 53.1 (2) |
C7'—O1'—C1'—O5' | 113.1 (3) | C1"—O5"—C5"—C6" | −175.25 (18) |
C7'—O1'—C1'—C2' | −125.8 (3) | C1"—O5"—C5"—C4" | 62.6 (2) |
C9'—O2'—C2'—C3' | 108.0 (2) | O4"—C4"—C5"—O5" | −174.17 (18) |
C9'—O2'—C2'—C1' | −133.0 (2) | C3"—C4"—C5"—O5" | −58.1 (2) |
O5'—C1'—C2'—O2' | −63.2 (3) | O4"—C4"—C5"—C6" | 67.6 (2) |
O1'—C1'—C2'—O2' | 176.8 (2) | C3"—C4"—C5"—C6" | −176.29 (19) |
O5'—C1'—C2'—C3' | 56.2 (3) | C15"—O6"—C6"—C5" | −178.52 (19) |
O1'—C1'—C2'—C3' | −63.9 (3) | O5"—C5"—C6"—O6" | 80.3 (2) |
C11'—O3'—C3'—C2' | −112.0 (3) | C4"—C5"—C6"—O6" | −160.38 (18) |
C11'—O3'—C3'—C4' | 125.7 (3) | C1"—O1"—C7"—O7" | 3.4 (4) |
O2'—C2'—C3'—O3' | −53.4 (3) | C1"—O1"—C7"—C8" | −176.5 (2) |
C1'—C2'—C3'—O3' | −170.3 (2) | C2"—O2"—C9"—O8" | −2.1 (4) |
O2'—C2'—C3'—C4' | 66.4 (3) | C2"—O2"—C9"—C10" | 177.8 (2) |
C1'—C2'—C3'—C4' | −50.5 (3) | C3"—O3"—C11"—O9" | −0.1 (5) |
C13'—O4'—C4'—C3' | 96.8 (3) | C3"—O3"—C11"—C12" | −178.5 (4) |
C13'—O4'—C4'—C5' | −144.0 (2) | C4"—O4"—C13"—O10" | 8.8 (4) |
O3'—C3'—C4'—O4' | −77.9 (2) | C4"—O4"—C13"—C14" | −172.1 (2) |
C2'—C3'—C4'—O4' | 161.83 (19) | C6"—O6"—C15"—O11" | 1.6 (4) |
O3'—C3'—C4'—C5' | 167.7 (2) | C6"—O6"—C15"—C16" | −178.6 (2) |
C40H54O27 | F(000) = 1020 |
Mr = 966.83 | Dx = 1.190 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.1043 (2) Å | Cell parameters from 9335 reflections |
b = 21.4770 (5) Å | θ = 3.8–71.6° |
c = 13.8106 (3) Å | µ = 0.88 mm−1 |
β = 91.8362 (8)° | T = 120 K |
V = 2699.04 (10) Å3 | Block, colorless |
Z = 2 | 0.19 × 0.15 × 0.12 mm |
Bruker APEXII CCD diffractometer | 9999 independent reflections |
Radiation source: Incoatec micro-focus | 9956 reflections with I > 2σ(I) |
MONTEL Multi-layer monochromator | Rint = 0.022 |
Detector resolution: 8.33 pixels mm-1 | θmax = 71.7°, θmin = 3.2° |
combination of ω and φ–scans | h = −11→11 |
Absorption correction: numerical (SADABS; Krause et al., 2015) | k = −24→26 |
Tmin = 0.864, Tmax = 0.950 | l = −16→16 |
72001 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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.061P)2 + 0.580P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.025 |
9999 reflections | Δρmax = 0.53 e Å−3 |
629 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack x determined using 4517 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: dual | Absolute structure parameter: 0.069 (17) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. One acetate was disordered over two sites. This group was modeled with occupancies summed to unity yielding a 0.83:0.17 ratio. Minor component atoms were modeled with isotropic displacement parameters. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.32946 (18) | 0.79339 (9) | 1.24283 (13) | 0.0372 (4) | |
O2 | 0.96145 (17) | 0.77217 (8) | 1.32418 (11) | 0.0288 (3) | |
O4 | 0.97619 (18) | 0.85795 (8) | 1.04730 (11) | 0.0297 (3) | |
O5 | 1.16089 (19) | 0.86883 (8) | 1.28676 (12) | 0.0335 (4) | |
O6 | 0.9541 (2) | 0.96229 (9) | 1.24464 (14) | 0.0455 (5) | |
O7 | 1.4749 (2) | 0.83303 (14) | 1.36352 (16) | 0.0594 (6) | |
O8 | 0.9267 (2) | 0.66907 (10) | 1.34400 (13) | 0.0423 (4) | |
O9 | 0.7595 (3) | 0.90429 (15) | 1.07179 (17) | 0.0676 (7) | |
O10 | 0.9104 (3) | 1.05340 (11) | 1.1710 (2) | 0.0629 (6) | |
C1 | 1.2023 (2) | 0.80665 (12) | 1.29819 (16) | 0.0304 (5) | |
H1 | 1.225878 | 0.798368 | 1.368235 | 0.036* | |
C2 | 1.0832 (2) | 0.76164 (11) | 1.26250 (15) | 0.0260 (4) | |
H2 | 1.118160 | 0.717596 | 1.267805 | 0.031* | |
C3 | 1.0383 (2) | 0.77745 (10) | 1.15805 (15) | 0.0231 (4) | |
H3 | 1.122849 | 0.768689 | 1.115607 | 0.028* | |
C4 | 0.9978 (2) | 0.84550 (11) | 1.14916 (15) | 0.0266 (4) | |
H4 | 0.905619 | 0.854203 | 1.184211 | 0.032* | |
C5 | 1.1236 (3) | 0.88684 (12) | 1.18868 (17) | 0.0319 (5) | |
H5 | 1.211328 | 0.880545 | 1.148084 | 0.038* | |
C6 | 1.0861 (4) | 0.95461 (13) | 1.1895 (2) | 0.0432 (6) | |
H6A | 1.168052 | 0.978744 | 1.219787 | 0.052* | |
H6B | 1.068916 | 0.969851 | 1.122453 | 0.052* | |
C7 | 1.4610 (3) | 0.81115 (18) | 1.2824 (2) | 0.0480 (7) | |
C8 | 1.5798 (3) | 0.8039 (2) | 1.2107 (2) | 0.0555 (8) | |
H8A | 1.566931 | 0.764318 | 1.176192 | 0.083* | |
H8B | 1.675891 | 0.804394 | 1.244747 | 0.083* | |
H8C | 1.574348 | 0.838348 | 1.164096 | 0.083* | |
C9 | 0.8956 (2) | 0.72171 (13) | 1.36255 (15) | 0.0329 (5) | |
C10 | 0.7813 (3) | 0.74238 (18) | 1.4313 (2) | 0.0484 (7) | |
H10A | 0.825860 | 0.770644 | 1.479556 | 0.073* | |
H10B | 0.741024 | 0.705974 | 1.464011 | 0.073* | |
H10C | 0.702105 | 0.764043 | 1.395252 | 0.073* | |
C11 | 0.8490 (3) | 0.88528 (13) | 1.0181 (2) | 0.0393 (6) | |
C12 | 0.8394 (4) | 0.88916 (14) | 0.9092 (2) | 0.0465 (7) | |
H12A | 0.933593 | 0.903646 | 0.885174 | 0.070* | |
H12B | 0.761638 | 0.918447 | 0.889362 | 0.070* | |
H12C | 0.816890 | 0.847902 | 0.882344 | 0.070* | |
C13 | 0.8733 (4) | 1.01297 (15) | 1.2252 (2) | 0.0507 (7) | |
C14 | 0.7319 (5) | 1.0111 (2) | 1.2775 (3) | 0.0684 (10) | |
H14A | 0.660227 | 0.985652 | 1.240745 | 0.103* | |
H14B | 0.693640 | 1.053466 | 1.284127 | 0.103* | |
H14C | 0.749204 | 0.992874 | 1.341944 | 0.103* | |
O1' | 0.91482 (15) | 0.74073 (7) | 1.12571 (10) | 0.0231 (3) | |
O3' | 0.60166 (16) | 0.60693 (8) | 1.01198 (11) | 0.0291 (3) | |
O4' | 0.77799 (18) | 0.54379 (7) | 1.15035 (12) | 0.0294 (3) | |
O5' | 1.03456 (15) | 0.65715 (7) | 1.05320 (11) | 0.0244 (3) | |
O6' | 1.21573 (19) | 0.59833 (9) | 1.19189 (15) | 0.0409 (4) | |
O7' | 0.46227 (19) | 0.68752 (10) | 1.05404 (16) | 0.0470 (5) | |
O8' | 0.8241 (3) | 0.45956 (10) | 1.06250 (19) | 0.0619 (7) | |
O9' | 1.3643 (3) | 0.51718 (13) | 1.1744 (2) | 0.0691 (7) | |
C1' | 0.9394 (2) | 0.70827 (10) | 1.03845 (14) | 0.0225 (4) | |
H1' | 0.983770 | 0.737512 | 0.991232 | 0.027* | |
C2' | 0.7874 (2) | 0.68834 (10) | 0.99914 (14) | 0.0217 (4) | |
H2' | 0.718829 | 0.724672 | 1.000364 | 0.026* | |
C3' | 0.7268 (2) | 0.63544 (10) | 1.06026 (15) | 0.0229 (4) | |
H3' | 0.696472 | 0.652549 | 1.123922 | 0.028* | |
C4' | 0.8386 (2) | 0.58428 (11) | 1.07812 (16) | 0.0257 (4) | |
H4' | 0.857478 | 0.560947 | 1.017110 | 0.031* | |
C5' | 0.9804 (2) | 0.61240 (11) | 1.12112 (16) | 0.0265 (4) | |
H5' | 0.959247 | 0.633807 | 1.183451 | 0.032* | |
C6' | 1.1005 (3) | 0.56551 (12) | 1.1382 (2) | 0.0354 (5) | |
H6'A | 1.064624 | 0.529754 | 1.176010 | 0.042* | |
H6'B | 1.136820 | 0.549934 | 1.075865 | 0.042* | |
C7' | 0.4762 (2) | 0.63990 (13) | 1.00940 (17) | 0.0329 (5) | |
C8' | 0.3613 (3) | 0.61019 (18) | 0.9454 (2) | 0.0481 (7) | |
H8'A | 0.380027 | 0.620060 | 0.877657 | 0.072* | |
H8'B | 0.264364 | 0.626033 | 0.962009 | 0.072* | |
H8'C | 0.364067 | 0.564955 | 0.954608 | 0.072* | |
C9' | 0.7745 (3) | 0.48212 (12) | 1.1325 (2) | 0.0365 (5) | |
C10' | 0.7014 (3) | 0.44865 (13) | 1.2128 (2) | 0.0445 (6) | |
H10D | 0.727363 | 0.468794 | 1.274682 | 0.067* | |
H10E | 0.734245 | 0.405206 | 1.214591 | 0.067* | |
H10F | 0.594556 | 0.450027 | 1.201744 | 0.067* | |
C11' | 1.3425 (3) | 0.56770 (15) | 1.2054 (2) | 0.0401 (6) | |
C12' | 1.4512 (3) | 0.60624 (18) | 1.2644 (2) | 0.0502 (7) | |
H12D | 1.444318 | 0.649862 | 1.243953 | 0.075* | |
H12E | 1.550943 | 0.590841 | 1.254420 | 0.075* | |
H12F | 1.429081 | 0.603040 | 1.333213 | 0.075* | |
O1" | 0.79559 (16) | 0.66567 (7) | 0.90249 (10) | 0.0245 (3) | |
O2" | 0.65352 (16) | 0.72501 (8) | 0.67704 (11) | 0.0301 (3) | |
O3" | 0.7728 (2) | 0.61961 (10) | 0.59800 (13) | 0.0403 (4) | |
O4" | 1.06682 (19) | 0.64213 (9) | 0.62981 (12) | 0.0364 (4) | |
O5" | 0.90143 (15) | 0.74439 (7) | 0.81021 (11) | 0.0252 (3) | |
O6" | 1.19047 (17) | 0.77016 (9) | 0.85856 (12) | 0.0342 (4) | |
O7" | 0.44704 (19) | 0.66900 (10) | 0.64753 (14) | 0.0432 (4) | |
O8" | 0.6641 (4) | 0.53560 (15) | 0.6712 (3) | 0.0749 (12) | 0.827 (5) |
O8"A | 0.8960 (18) | 0.5289 (8) | 0.6032 (12) | 0.067 (4)* | 0.173 (5) |
O9" | 1.11849 (19) | 0.71860 (11) | 0.52457 (12) | 0.0426 (5) | |
O10" | 1.4233 (2) | 0.78024 (13) | 0.81525 (15) | 0.0535 (6) | |
C1" | 0.7713 (2) | 0.71123 (11) | 0.83031 (15) | 0.0252 (4) | |
H1" | 0.696169 | 0.741383 | 0.853092 | 0.030* | |
C2" | 0.7082 (2) | 0.67716 (11) | 0.74130 (16) | 0.0289 (5) | |
H2" | 0.626432 | 0.648987 | 0.759996 | 0.035* | |
C3" | 0.8267 (3) | 0.64023 (12) | 0.69179 (16) | 0.0309 (5) | |
H3" | 0.856099 | 0.603497 | 0.732466 | 0.037* | |
C4" | 0.9596 (2) | 0.68095 (12) | 0.67517 (16) | 0.0293 (5) | |
H4" | 0.931504 | 0.716337 | 0.631313 | 0.035* | |
C5" | 1.0168 (2) | 0.70609 (11) | 0.77303 (15) | 0.0262 (4) | |
H5" | 1.039210 | 0.670872 | 0.818503 | 0.031* | |
C6" | 1.1499 (3) | 0.74652 (13) | 0.76334 (17) | 0.0343 (5) | |
H6"A | 1.231806 | 0.722003 | 0.737239 | 0.041* | |
H6"B | 1.127658 | 0.781453 | 0.718454 | 0.041* | |
C7" | 0.5163 (2) | 0.71590 (14) | 0.63722 (15) | 0.0334 (5) | |
C8" | 0.4666 (3) | 0.77199 (17) | 0.58164 (19) | 0.0459 (7) | |
H8"A | 0.428342 | 0.803021 | 0.626344 | 0.069* | |
H8"B | 0.389012 | 0.760127 | 0.534374 | 0.069* | |
H8"C | 0.549749 | 0.789685 | 0.547678 | 0.069* | |
C9" | 0.6923 (5) | 0.56459 (19) | 0.5992 (3) | 0.0590 (12) | 0.827 (5) |
C10" | 0.6462 (8) | 0.5496 (3) | 0.4958 (5) | 0.094 (2) | 0.827 (5) |
H10G | 0.575481 | 0.580872 | 0.471818 | 0.141* | 0.827 (5) |
H10H | 0.600520 | 0.508332 | 0.493071 | 0.141* | 0.827 (5) |
H10I | 0.732697 | 0.550003 | 0.455325 | 0.141* | 0.827 (5) |
C9"A | 0.8129 (19) | 0.5637 (9) | 0.5572 (12) | 0.046 (4)* | 0.173 (5) |
C10A | 0.751 (2) | 0.5543 (9) | 0.4603 (12) | 0.043 (4)* | 0.173 (5) |
H10J | 0.697893 | 0.591805 | 0.439312 | 0.064* | 0.173 (5) |
H10K | 0.683720 | 0.518809 | 0.460329 | 0.064* | 0.173 (5) |
H10L | 0.830701 | 0.545972 | 0.415848 | 0.064* | 0.173 (5) |
C11" | 1.1276 (3) | 0.66525 (16) | 0.54952 (17) | 0.0389 (6) | |
C12" | 1.2047 (4) | 0.6143 (2) | 0.4952 (2) | 0.0578 (9) | |
H12G | 1.259581 | 0.587797 | 0.541411 | 0.087* | |
H12H | 1.272811 | 0.633023 | 0.450011 | 0.087* | |
H12I | 1.131801 | 0.589177 | 0.459122 | 0.087* | |
C13" | 1.3317 (2) | 0.78755 (12) | 0.87336 (17) | 0.0309 (5) | |
C14" | 1.3529 (3) | 0.81831 (13) | 0.97007 (18) | 0.0354 (5) | |
H14D | 1.283633 | 0.852989 | 0.975086 | 0.053* | |
H14E | 1.453731 | 0.834090 | 0.976987 | 0.053* | |
H14F | 1.335362 | 0.787995 | 1.021456 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0215 (8) | 0.0545 (12) | 0.0355 (9) | −0.0020 (7) | −0.0005 (6) | −0.0056 (8) |
O2 | 0.0247 (7) | 0.0377 (9) | 0.0242 (7) | 0.0046 (6) | 0.0023 (6) | 0.0047 (6) |
O4 | 0.0352 (8) | 0.0295 (8) | 0.0243 (7) | −0.0031 (6) | −0.0011 (6) | 0.0047 (6) |
O5 | 0.0375 (9) | 0.0344 (9) | 0.0282 (8) | −0.0027 (7) | −0.0034 (6) | −0.0044 (6) |
O6 | 0.0686 (13) | 0.0332 (10) | 0.0346 (9) | 0.0104 (9) | 0.0013 (8) | −0.0015 (7) |
O7 | 0.0420 (11) | 0.0921 (19) | 0.0433 (11) | −0.0109 (11) | −0.0121 (9) | 0.0029 (11) |
O8 | 0.0493 (11) | 0.0454 (12) | 0.0322 (9) | −0.0117 (9) | 0.0031 (8) | 0.0055 (8) |
O9 | 0.0548 (13) | 0.099 (2) | 0.0487 (12) | 0.0307 (14) | 0.0019 (10) | 0.0128 (12) |
O10 | 0.0669 (14) | 0.0381 (12) | 0.0818 (17) | −0.0008 (10) | −0.0240 (12) | 0.0112 (12) |
C1 | 0.0242 (10) | 0.0406 (13) | 0.0262 (10) | 0.0017 (9) | −0.0013 (8) | −0.0023 (9) |
C2 | 0.0227 (10) | 0.0304 (12) | 0.0249 (10) | 0.0018 (8) | 0.0014 (8) | −0.0002 (8) |
C3 | 0.0173 (8) | 0.0271 (11) | 0.0248 (10) | −0.0013 (8) | 0.0005 (7) | 0.0013 (8) |
C4 | 0.0287 (10) | 0.0289 (12) | 0.0221 (9) | −0.0023 (8) | 0.0004 (8) | 0.0019 (8) |
C5 | 0.0373 (12) | 0.0318 (13) | 0.0266 (11) | −0.0067 (10) | −0.0002 (9) | −0.0024 (9) |
C6 | 0.0641 (17) | 0.0309 (14) | 0.0345 (13) | −0.0069 (12) | −0.0010 (12) | −0.0008 (10) |
C7 | 0.0286 (12) | 0.078 (2) | 0.0372 (14) | −0.0008 (13) | −0.0060 (10) | 0.0171 (13) |
C8 | 0.0259 (12) | 0.097 (3) | 0.0431 (15) | −0.0058 (14) | −0.0042 (11) | 0.0111 (16) |
C9 | 0.0281 (11) | 0.0481 (16) | 0.0222 (9) | −0.0015 (10) | −0.0026 (8) | 0.0061 (9) |
C10 | 0.0343 (13) | 0.076 (2) | 0.0354 (13) | 0.0078 (13) | 0.0104 (10) | 0.0155 (13) |
C11 | 0.0389 (13) | 0.0395 (14) | 0.0394 (13) | −0.0001 (11) | −0.0027 (10) | 0.0117 (11) |
C12 | 0.0604 (17) | 0.0399 (15) | 0.0381 (14) | −0.0014 (13) | −0.0146 (12) | 0.0119 (11) |
C13 | 0.0659 (19) | 0.0357 (15) | 0.0489 (16) | 0.0058 (14) | −0.0224 (14) | −0.0088 (12) |
C14 | 0.072 (2) | 0.055 (2) | 0.077 (2) | 0.0185 (18) | −0.0012 (19) | −0.0107 (18) |
O1' | 0.0190 (6) | 0.0274 (8) | 0.0228 (7) | −0.0023 (6) | 0.0017 (5) | −0.0001 (6) |
O3' | 0.0196 (7) | 0.0344 (9) | 0.0332 (8) | −0.0050 (6) | −0.0014 (6) | −0.0022 (6) |
O4' | 0.0308 (8) | 0.0260 (9) | 0.0314 (8) | −0.0018 (6) | 0.0018 (6) | 0.0030 (6) |
O5' | 0.0172 (6) | 0.0269 (8) | 0.0292 (7) | 0.0011 (5) | 0.0017 (5) | 0.0004 (6) |
O6' | 0.0251 (8) | 0.0450 (11) | 0.0520 (11) | 0.0065 (7) | −0.0089 (7) | 0.0010 (8) |
O7' | 0.0261 (8) | 0.0524 (12) | 0.0621 (12) | 0.0081 (8) | −0.0041 (8) | −0.0075 (10) |
O8' | 0.0851 (17) | 0.0298 (11) | 0.0729 (15) | −0.0036 (11) | 0.0384 (13) | −0.0094 (10) |
O9' | 0.0382 (11) | 0.0646 (16) | 0.103 (2) | 0.0222 (11) | −0.0150 (12) | −0.0050 (15) |
C1' | 0.0194 (9) | 0.0250 (11) | 0.0231 (9) | 0.0004 (8) | 0.0011 (7) | 0.0022 (8) |
C2' | 0.0185 (9) | 0.0240 (10) | 0.0226 (9) | 0.0006 (7) | 0.0000 (7) | 0.0012 (8) |
C3' | 0.0164 (8) | 0.0270 (10) | 0.0253 (9) | −0.0026 (8) | −0.0011 (7) | −0.0003 (8) |
C4' | 0.0208 (9) | 0.0271 (11) | 0.0293 (10) | −0.0009 (8) | 0.0021 (8) | 0.0007 (8) |
C5' | 0.0224 (10) | 0.0260 (11) | 0.0309 (10) | 0.0018 (8) | −0.0002 (8) | 0.0031 (8) |
C6' | 0.0237 (10) | 0.0315 (13) | 0.0506 (14) | 0.0027 (9) | −0.0037 (9) | 0.0025 (10) |
C7' | 0.0201 (10) | 0.0457 (15) | 0.0328 (11) | −0.0009 (9) | 0.0003 (8) | 0.0048 (10) |
C8' | 0.0253 (12) | 0.075 (2) | 0.0436 (14) | −0.0093 (12) | −0.0057 (10) | −0.0007 (14) |
C9' | 0.0339 (12) | 0.0261 (13) | 0.0497 (14) | 0.0010 (9) | 0.0037 (10) | 0.0027 (10) |
C10' | 0.0458 (14) | 0.0316 (14) | 0.0563 (16) | −0.0016 (11) | 0.0045 (12) | 0.0132 (12) |
C11' | 0.0256 (11) | 0.0552 (18) | 0.0396 (13) | 0.0072 (11) | 0.0002 (9) | 0.0143 (12) |
C12' | 0.0298 (12) | 0.085 (2) | 0.0349 (13) | 0.0026 (13) | −0.0076 (10) | 0.0069 (14) |
O1" | 0.0223 (7) | 0.0292 (8) | 0.0218 (7) | 0.0010 (6) | −0.0010 (5) | 0.0015 (6) |
O2" | 0.0210 (7) | 0.0436 (10) | 0.0254 (7) | 0.0025 (6) | −0.0026 (6) | 0.0071 (6) |
O3" | 0.0364 (9) | 0.0518 (12) | 0.0318 (9) | 0.0058 (8) | −0.0106 (7) | −0.0108 (8) |
O4" | 0.0329 (8) | 0.0456 (11) | 0.0307 (8) | 0.0138 (7) | −0.0002 (6) | −0.0053 (7) |
O5" | 0.0194 (7) | 0.0294 (8) | 0.0268 (7) | 0.0009 (6) | 0.0022 (5) | 0.0015 (6) |
O6" | 0.0216 (7) | 0.0519 (11) | 0.0292 (8) | −0.0055 (7) | 0.0043 (6) | −0.0076 (7) |
O7" | 0.0292 (8) | 0.0564 (12) | 0.0432 (10) | −0.0028 (8) | −0.0102 (7) | 0.0026 (9) |
O8" | 0.077 (2) | 0.0451 (17) | 0.099 (3) | −0.0130 (14) | −0.0519 (19) | 0.0082 (16) |
O9" | 0.0305 (9) | 0.0683 (14) | 0.0290 (8) | 0.0070 (8) | 0.0016 (6) | 0.0020 (9) |
O10" | 0.0249 (8) | 0.0895 (17) | 0.0465 (11) | −0.0099 (9) | 0.0095 (8) | −0.0226 (11) |
C1" | 0.0189 (9) | 0.0320 (11) | 0.0245 (9) | 0.0000 (8) | 0.0000 (7) | 0.0033 (8) |
C2" | 0.0218 (9) | 0.0366 (13) | 0.0281 (10) | −0.0008 (8) | −0.0052 (8) | 0.0042 (9) |
C3" | 0.0303 (11) | 0.0361 (13) | 0.0256 (10) | 0.0033 (9) | −0.0091 (8) | −0.0012 (9) |
C4" | 0.0246 (10) | 0.0385 (13) | 0.0248 (10) | 0.0076 (9) | −0.0005 (8) | −0.0004 (9) |
C5" | 0.0203 (9) | 0.0348 (13) | 0.0235 (9) | 0.0038 (8) | 0.0012 (7) | −0.0008 (8) |
C6" | 0.0243 (10) | 0.0513 (15) | 0.0275 (10) | −0.0030 (10) | 0.0038 (8) | −0.0014 (10) |
C7" | 0.0214 (10) | 0.0575 (16) | 0.0214 (9) | 0.0056 (10) | 0.0013 (8) | 0.0008 (10) |
C8" | 0.0278 (12) | 0.075 (2) | 0.0347 (13) | 0.0109 (12) | −0.0026 (10) | 0.0181 (13) |
C9" | 0.061 (2) | 0.043 (2) | 0.070 (3) | 0.0132 (17) | −0.041 (2) | −0.0164 (19) |
C10" | 0.110 (5) | 0.076 (4) | 0.092 (4) | 0.025 (3) | −0.067 (4) | −0.044 (3) |
C11" | 0.0257 (11) | 0.0667 (19) | 0.0239 (10) | 0.0133 (11) | −0.0040 (8) | −0.0069 (11) |
C12" | 0.0461 (16) | 0.089 (3) | 0.0379 (14) | 0.0265 (16) | −0.0003 (12) | −0.0200 (15) |
C13" | 0.0233 (10) | 0.0370 (13) | 0.0323 (11) | 0.0007 (9) | 0.0026 (8) | 0.0010 (9) |
C14" | 0.0278 (11) | 0.0433 (15) | 0.0349 (12) | −0.0026 (10) | −0.0008 (9) | −0.0024 (10) |
O1—C7 | 1.355 (3) | C5'—H5' | 1.0000 |
O1—C1 | 1.436 (3) | C6'—H6'A | 0.9900 |
O2—C9 | 1.355 (3) | C6'—H6'B | 0.9900 |
O2—C2 | 1.437 (3) | C7'—C8' | 1.491 (4) |
O4—C11 | 1.348 (3) | C8'—H8'A | 0.9800 |
O4—C4 | 1.439 (3) | C8'—H8'B | 0.9800 |
O5—C1 | 1.395 (3) | C8'—H8'C | 0.9800 |
O5—C5 | 1.439 (3) | C9'—C10' | 1.496 (4) |
O6—C13 | 1.336 (4) | C10'—H10D | 0.9800 |
O6—C6 | 1.452 (4) | C10'—H10E | 0.9800 |
O7—C7 | 1.217 (4) | C10'—H10F | 0.9800 |
O8—C9 | 1.195 (4) | C11'—C12' | 1.510 (4) |
O9—C11 | 1.191 (4) | C12'—H12D | 0.9800 |
O10—C13 | 1.202 (4) | C12'—H12E | 0.9800 |
C1—C2 | 1.523 (3) | C12'—H12F | 0.9800 |
C1—H1 | 1.0000 | O1"—C1" | 1.409 (3) |
C2—C3 | 1.525 (3) | O2"—C7" | 1.363 (3) |
C2—H2 | 1.0000 | O2"—C2" | 1.436 (3) |
C3—O1' | 1.433 (2) | O3"—C9"A | 1.380 (19) |
C3—C4 | 1.511 (3) | O3"—C9" | 1.391 (5) |
C3—H3 | 1.0000 | O3"—C3" | 1.440 (3) |
C4—C5 | 1.535 (3) | O4"—C11" | 1.350 (3) |
C4—H4 | 1.0000 | O4"—C4" | 1.442 (3) |
C5—C6 | 1.495 (4) | O5"—C1" | 1.418 (3) |
C5—H5 | 1.0000 | O5"—C5" | 1.441 (2) |
C6—H6A | 0.9900 | O6"—C13" | 1.348 (3) |
C6—H6B | 0.9900 | O6"—C6" | 1.446 (3) |
C7—C8 | 1.499 (4) | O7"—C7" | 1.199 (4) |
C8—H8A | 0.9800 | O8"—C9" | 1.208 (6) |
C8—H8B | 0.9800 | O8"A—C9"A | 1.23 (2) |
C8—H8C | 0.9800 | O9"—C11" | 1.199 (4) |
C9—C10 | 1.498 (3) | O10"—C13" | 1.186 (3) |
C10—H10A | 0.9800 | C1"—C2" | 1.527 (3) |
C10—H10B | 0.9800 | C1"—H1" | 1.0000 |
C10—H10C | 0.9800 | C2"—C3" | 1.519 (3) |
C11—C12 | 1.506 (4) | C2"—H2" | 1.0000 |
C12—H12A | 0.9800 | C3"—C4" | 1.516 (3) |
C12—H12B | 0.9800 | C3"—H3" | 1.0000 |
C12—H12C | 0.9800 | C4"—C5" | 1.531 (3) |
C13—C14 | 1.498 (6) | C4"—H4" | 1.0000 |
C14—H14A | 0.9800 | C5"—C6" | 1.501 (3) |
C14—H14B | 0.9800 | C5"—H5" | 1.0000 |
C14—H14C | 0.9800 | C6"—H6"A | 0.9900 |
O1'—C1' | 1.416 (2) | C6"—H6"B | 0.9900 |
O3'—C7' | 1.343 (3) | C7"—C8" | 1.491 (4) |
O3'—C3' | 1.438 (2) | C8"—H8"A | 0.9800 |
O4'—C9' | 1.347 (3) | C8"—H8"B | 0.9800 |
O4'—C4' | 1.446 (3) | C8"—H8"C | 0.9800 |
O5'—C1' | 1.409 (3) | C9"—C10" | 1.510 (6) |
O5'—C5' | 1.441 (3) | C10"—H10G | 0.9800 |
O6'—C11' | 1.336 (3) | C10"—H10H | 0.9800 |
O6'—C6' | 1.449 (3) | C10"—H10I | 0.9800 |
O7'—C7' | 1.203 (3) | C9"A—C10A | 1.45 (2) |
O8'—C9' | 1.184 (3) | C10A—H10J | 0.9800 |
O9'—C11' | 1.185 (4) | C10A—H10K | 0.9800 |
C1'—C2' | 1.531 (3) | C10A—H10L | 0.9800 |
C1'—H1' | 1.0000 | C11"—C12" | 1.511 (4) |
C2'—O1" | 1.425 (2) | C12"—H12G | 0.9800 |
C2'—C3' | 1.529 (3) | C12"—H12H | 0.9800 |
C2'—H2' | 1.0000 | C12"—H12I | 0.9800 |
C3'—C4' | 1.512 (3) | C13"—C14" | 1.497 (3) |
C3'—H3' | 1.0000 | C14"—H14D | 0.9800 |
C4'—C5' | 1.528 (3) | C14"—H14E | 0.9800 |
C4'—H4' | 1.0000 | C14"—H14F | 0.9800 |
C5'—C6' | 1.500 (3) | ||
C7—O1—C1 | 116.5 (2) | H6'A—C6'—H6'B | 108.8 |
C9—O2—C2 | 117.74 (18) | O7'—C7'—O3' | 122.6 (2) |
C11—O4—C4 | 117.53 (19) | O7'—C7'—C8' | 125.7 (2) |
C1—O5—C5 | 114.75 (18) | O3'—C7'—C8' | 111.7 (2) |
C13—O6—C6 | 116.5 (3) | C7'—C8'—H8'A | 109.5 |
O5—C1—O1 | 110.4 (2) | C7'—C8'—H8'B | 109.5 |
O5—C1—C2 | 112.55 (18) | H8'A—C8'—H8'B | 109.5 |
O1—C1—C2 | 106.23 (18) | C7'—C8'—H8'C | 109.5 |
O5—C1—H1 | 109.2 | H8'A—C8'—H8'C | 109.5 |
O1—C1—H1 | 109.2 | H8'B—C8'—H8'C | 109.5 |
C2—C1—H1 | 109.2 | O8'—C9'—O4' | 123.0 (2) |
O2—C2—C1 | 105.25 (17) | O8'—C9'—C10' | 126.8 (3) |
O2—C2—C3 | 109.71 (16) | O4'—C9'—C10' | 110.2 (2) |
C1—C2—C3 | 109.35 (18) | C9'—C10'—H10D | 109.5 |
O2—C2—H2 | 110.8 | C9'—C10'—H10E | 109.5 |
C1—C2—H2 | 110.8 | H10D—C10'—H10E | 109.5 |
C3—C2—H2 | 110.8 | C9'—C10'—H10F | 109.5 |
O1'—C3—C4 | 108.66 (16) | H10D—C10'—H10F | 109.5 |
O1'—C3—C2 | 110.86 (16) | H10E—C10'—H10F | 109.5 |
C4—C3—C2 | 110.45 (18) | O9'—C11'—O6' | 123.7 (3) |
O1'—C3—H3 | 108.9 | O9'—C11'—C12' | 125.6 (3) |
C4—C3—H3 | 108.9 | O6'—C11'—C12' | 110.7 (3) |
C2—C3—H3 | 108.9 | C11'—C12'—H12D | 109.5 |
O4—C4—C3 | 106.53 (18) | C11'—C12'—H12E | 109.5 |
O4—C4—C5 | 108.50 (17) | H12D—C12'—H12E | 109.5 |
C3—C4—C5 | 110.68 (18) | C11'—C12'—H12F | 109.5 |
O4—C4—H4 | 110.3 | H12D—C12'—H12F | 109.5 |
C3—C4—H4 | 110.3 | H12E—C12'—H12F | 109.5 |
C5—C4—H4 | 110.3 | C1"—O1"—C2' | 114.44 (16) |
O5—C5—C6 | 107.6 (2) | C7"—O2"—C2" | 116.23 (19) |
O5—C5—C4 | 109.28 (18) | C9"A—O3"—C3" | 123.2 (7) |
C6—C5—C4 | 113.5 (2) | C9"—O3"—C3" | 114.6 (3) |
O5—C5—H5 | 108.8 | C11"—O4"—C4" | 116.4 (2) |
C6—C5—H5 | 108.8 | C1"—O5"—C5" | 113.96 (17) |
C4—C5—H5 | 108.8 | C13"—O6"—C6" | 116.71 (17) |
O6—C6—C5 | 107.9 (2) | O1"—C1"—O5" | 111.97 (16) |
O6—C6—H6A | 110.1 | O1"—C1"—C2" | 106.46 (18) |
C5—C6—H6A | 110.1 | O5"—C1"—C2" | 112.22 (17) |
O6—C6—H6B | 110.1 | O1"—C1"—H1" | 108.7 |
C5—C6—H6B | 110.1 | O5"—C1"—H1" | 108.7 |
H6A—C6—H6B | 108.4 | C2"—C1"—H1" | 108.7 |
O7—C7—O1 | 123.0 (3) | O2"—C2"—C3" | 109.43 (18) |
O7—C7—C8 | 126.3 (3) | O2"—C2"—C1" | 105.58 (18) |
O1—C7—C8 | 110.6 (2) | C3"—C2"—C1" | 111.01 (17) |
C7—C8—H8A | 109.5 | O2"—C2"—H2" | 110.2 |
C7—C8—H8B | 109.5 | C3"—C2"—H2" | 110.2 |
H8A—C8—H8B | 109.5 | C1"—C2"—H2" | 110.2 |
C7—C8—H8C | 109.5 | O3"—C3"—C4" | 106.99 (19) |
H8A—C8—H8C | 109.5 | O3"—C3"—C2" | 109.80 (18) |
H8B—C8—H8C | 109.5 | C4"—C3"—C2" | 110.4 (2) |
O8—C9—O2 | 124.2 (2) | O3"—C3"—H3" | 109.9 |
O8—C9—C10 | 126.2 (3) | C4"—C3"—H3" | 109.9 |
O2—C9—C10 | 109.6 (2) | C2"—C3"—H3" | 109.9 |
C9—C10—H10A | 109.5 | O4"—C4"—C3" | 106.7 (2) |
C9—C10—H10B | 109.5 | O4"—C4"—C5" | 111.83 (17) |
H10A—C10—H10B | 109.5 | C3"—C4"—C5" | 108.67 (18) |
C9—C10—H10C | 109.5 | O4"—C4"—H4" | 109.9 |
H10A—C10—H10C | 109.5 | C3"—C4"—H4" | 109.9 |
H10B—C10—H10C | 109.5 | C5"—C4"—H4" | 109.9 |
O9—C11—O4 | 124.2 (3) | O5"—C5"—C6" | 107.54 (19) |
O9—C11—C12 | 125.7 (3) | O5"—C5"—C4" | 106.55 (16) |
O4—C11—C12 | 110.1 (2) | C6"—C5"—C4" | 112.21 (18) |
C11—C12—H12A | 109.5 | O5"—C5"—H5" | 110.1 |
C11—C12—H12B | 109.5 | C6"—C5"—H5" | 110.1 |
H12A—C12—H12B | 109.5 | C4"—C5"—H5" | 110.1 |
C11—C12—H12C | 109.5 | O6"—C6"—C5" | 107.78 (17) |
H12A—C12—H12C | 109.5 | O6"—C6"—H6"A | 110.2 |
H12B—C12—H12C | 109.5 | C5"—C6"—H6"A | 110.2 |
O10—C13—O6 | 123.4 (3) | O6"—C6"—H6"B | 110.2 |
O10—C13—C14 | 125.7 (3) | C5"—C6"—H6"B | 110.2 |
O6—C13—C14 | 110.9 (3) | H6"A—C6"—H6"B | 108.5 |
C13—C14—H14A | 109.5 | O7"—C7"—O2" | 123.5 (2) |
C13—C14—H14B | 109.5 | O7"—C7"—C8" | 126.0 (2) |
H14A—C14—H14B | 109.5 | O2"—C7"—C8" | 110.5 (2) |
C13—C14—H14C | 109.5 | C7"—C8"—H8"A | 109.5 |
H14A—C14—H14C | 109.5 | C7"—C8"—H8"B | 109.5 |
H14B—C14—H14C | 109.5 | H8"A—C8"—H8"B | 109.5 |
C1'—O1'—C3 | 113.11 (15) | C7"—C8"—H8"C | 109.5 |
C7'—O3'—C3' | 116.62 (18) | H8"A—C8"—H8"C | 109.5 |
C9'—O4'—C4' | 118.19 (19) | H8"B—C8"—H8"C | 109.5 |
C1'—O5'—C5' | 113.07 (15) | O8"—C9"—O3" | 125.0 (3) |
C11'—O6'—C6' | 116.1 (2) | O8"—C9"—C10" | 127.5 (5) |
O5'—C1'—O1' | 111.93 (16) | O3"—C9"—C10" | 107.5 (5) |
O5'—C1'—C2' | 112.21 (17) | C9"—C10"—H10G | 109.5 |
O1'—C1'—C2' | 105.90 (16) | C9"—C10"—H10H | 109.5 |
O5'—C1'—H1' | 108.9 | H10G—C10"—H10H | 109.5 |
O1'—C1'—H1' | 108.9 | C9"—C10"—H10I | 109.5 |
C2'—C1'—H1' | 108.9 | H10G—C10"—H10I | 109.5 |
O1"—C2'—C3' | 107.08 (17) | H10H—C10"—H10I | 109.5 |
O1"—C2'—C1' | 110.75 (16) | O8"A—C9"A—O3" | 119.1 (15) |
C3'—C2'—C1' | 110.49 (16) | O8"A—C9"A—C10A | 127.4 (18) |
O1"—C2'—H2' | 109.5 | O3"—C9"A—C10A | 113.5 (14) |
C3'—C2'—H2' | 109.5 | C9"A—C10A—H10J | 109.5 |
C1'—C2'—H2' | 109.5 | C9"A—C10A—H10K | 109.5 |
O3'—C3'—C4' | 106.58 (17) | H10J—C10A—H10K | 109.5 |
O3'—C3'—C2' | 110.79 (16) | C9"A—C10A—H10L | 109.5 |
C4'—C3'—C2' | 112.14 (16) | H10J—C10A—H10L | 109.5 |
O3'—C3'—H3' | 109.1 | H10K—C10A—H10L | 109.5 |
C4'—C3'—H3' | 109.1 | O9"—C11"—O4" | 124.2 (2) |
C2'—C3'—H3' | 109.1 | O9"—C11"—C12" | 125.3 (3) |
O4'—C4'—C3' | 106.25 (16) | O4"—C11"—C12" | 110.5 (3) |
O4'—C4'—C5' | 107.81 (17) | C11"—C12"—H12G | 109.5 |
C3'—C4'—C5' | 109.39 (18) | C11"—C12"—H12H | 109.5 |
O4'—C4'—H4' | 111.1 | H12G—C12"—H12H | 109.5 |
C3'—C4'—H4' | 111.1 | C11"—C12"—H12I | 109.5 |
C5'—C4'—H4' | 111.1 | H12G—C12"—H12I | 109.5 |
O5'—C5'—C6' | 106.68 (18) | H12H—C12"—H12I | 109.5 |
O5'—C5'—C4' | 108.25 (17) | O10"—C13"—O6" | 123.3 (2) |
C6'—C5'—C4' | 113.47 (19) | O10"—C13"—C14" | 126.0 (2) |
O5'—C5'—H5' | 109.4 | O6"—C13"—C14" | 110.66 (19) |
C6'—C5'—H5' | 109.4 | C13"—C14"—H14D | 109.5 |
C4'—C5'—H5' | 109.4 | C13"—C14"—H14E | 109.5 |
O6'—C6'—C5' | 105.4 (2) | H14D—C14"—H14E | 109.5 |
O6'—C6'—H6'A | 110.7 | C13"—C14"—H14F | 109.5 |
C5'—C6'—H6'A | 110.7 | H14D—C14"—H14F | 109.5 |
O6'—C6'—H6'B | 110.7 | H14E—C14"—H14F | 109.5 |
C5'—C6'—H6'B | 110.7 | ||
C5—O5—C1—O1 | 60.1 (2) | C1'—O5'—C5'—C4' | 64.3 (2) |
C5—O5—C1—C2 | −58.4 (2) | O4'—C4'—C5'—O5' | −174.82 (17) |
C7—O1—C1—O5 | 79.9 (3) | C3'—C4'—C5'—O5' | −59.7 (2) |
C7—O1—C1—C2 | −157.8 (2) | O4'—C4'—C5'—C6' | 67.0 (2) |
C9—O2—C2—C1 | −132.62 (19) | C3'—C4'—C5'—C6' | −177.91 (19) |
C9—O2—C2—C3 | 109.8 (2) | C11'—O6'—C6'—C5' | −172.2 (2) |
O5—C1—C2—O2 | −63.7 (2) | O5'—C5'—C6'—O6' | 69.4 (2) |
O1—C1—C2—O2 | 175.35 (17) | C4'—C5'—C6'—O6' | −171.50 (19) |
O5—C1—C2—C3 | 54.1 (2) | C3'—O3'—C7'—O7' | −8.3 (3) |
O1—C1—C2—C3 | −66.9 (2) | C3'—O3'—C7'—C8' | 171.5 (2) |
O2—C2—C3—O1' | −58.4 (2) | C4'—O4'—C9'—O8' | 3.1 (4) |
C1—C2—C3—O1' | −173.35 (17) | C4'—O4'—C9'—C10' | −177.1 (2) |
O2—C2—C3—C4 | 62.1 (2) | C6'—O6'—C11'—O9' | 1.6 (4) |
C1—C2—C3—C4 | −52.8 (2) | C6'—O6'—C11'—C12' | −178.5 (2) |
C11—O4—C4—C3 | 127.6 (2) | C3'—C2'—O1"—C1" | 147.46 (16) |
C11—O4—C4—C5 | −113.2 (2) | C1'—C2'—O1"—C1" | −92.0 (2) |
O1'—C3—C4—O4 | −65.6 (2) | C2'—O1"—C1"—O5" | 85.0 (2) |
C2—C3—C4—O4 | 172.57 (16) | C2'—O1"—C1"—C2" | −152.05 (16) |
O1'—C3—C4—C5 | 176.61 (16) | C5"—O5"—C1"—O1" | 62.2 (2) |
C2—C3—C4—C5 | 54.8 (2) | C5"—O5"—C1"—C2" | −57.5 (2) |
C1—O5—C5—C6 | −178.5 (2) | C7"—O2"—C2"—C3" | 107.3 (2) |
C1—O5—C5—C4 | 57.9 (3) | C7"—O2"—C2"—C1" | −133.17 (19) |
O4—C4—C5—O5 | −171.84 (18) | O1"—C1"—C2"—O2" | 167.27 (16) |
C3—C4—C5—O5 | −55.3 (2) | O5"—C1"—C2"—O2" | −69.9 (2) |
O4—C4—C5—C6 | 68.1 (2) | O1"—C1"—C2"—C3" | −74.2 (2) |
C3—C4—C5—C6 | −175.3 (2) | O5"—C1"—C2"—C3" | 48.6 (2) |
C13—O6—C6—C5 | −156.1 (2) | C9"A—O3"—C3"—C4" | 94.1 (9) |
O5—C5—C6—O6 | −65.2 (3) | C9"—O3"—C3"—C4" | 155.8 (2) |
C4—C5—C6—O6 | 55.8 (3) | C9"A—O3"—C3"—C2" | −146.1 (9) |
C1—O1—C7—O7 | 5.3 (4) | C9"—O3"—C3"—C2" | −84.3 (3) |
C1—O1—C7—C8 | −170.9 (3) | O2"—C2"—C3"—O3" | −51.7 (3) |
C2—O2—C9—O8 | −4.5 (3) | C1"—C2"—C3"—O3" | −167.86 (19) |
C2—O2—C9—C10 | 174.87 (19) | O2"—C2"—C3"—C4" | 66.0 (2) |
C4—O4—C11—O9 | 6.5 (4) | C1"—C2"—C3"—C4" | −50.1 (2) |
C4—O4—C11—C12 | −174.7 (2) | C11"—O4"—C4"—C3" | 130.7 (2) |
C6—O6—C13—O10 | −5.7 (4) | C11"—O4"—C4"—C5" | −110.7 (2) |
C6—O6—C13—C14 | 172.9 (3) | O3"—C3"—C4"—O4" | −61.6 (2) |
C4—C3—O1'—C1' | 111.97 (18) | C2"—C3"—C4"—O4" | 178.99 (16) |
C2—C3—O1'—C1' | −126.47 (18) | O3"—C3"—C4"—C5" | 177.71 (18) |
C5'—O5'—C1'—O1' | 59.1 (2) | C2"—C3"—C4"—C5" | 58.3 (2) |
C5'—O5'—C1'—C2' | −59.8 (2) | C1"—O5"—C5"—C6" | −175.40 (16) |
C3—O1'—C1'—O5' | 74.0 (2) | C1"—O5"—C5"—C4" | 64.1 (2) |
C3—O1'—C1'—C2' | −163.46 (16) | O4"—C4"—C5"—O5" | 179.36 (18) |
O5'—C1'—C2'—O1" | −68.7 (2) | C3"—C4"—C5"—O5" | −63.2 (2) |
O1'—C1'—C2'—O1" | 168.93 (16) | O4"—C4"—C5"—C6" | 61.9 (3) |
O5'—C1'—C2'—C3' | 49.8 (2) | C3"—C4"—C5"—C6" | 179.4 (2) |
O1'—C1'—C2'—C3' | −72.6 (2) | C13"—O6"—C6"—C5" | 156.3 (2) |
C7'—O3'—C3'—C4' | 164.71 (18) | O5"—C5"—C6"—O6" | 60.4 (2) |
C7'—O3'—C3'—C2' | −73.0 (2) | C4"—C5"—C6"—O6" | 177.25 (19) |
O1"—C2'—C3'—O3' | −46.1 (2) | C2"—O2"—C7"—O7" | −5.8 (3) |
C1'—C2'—C3'—O3' | −166.79 (16) | C2"—O2"—C7"—C8" | 173.5 (2) |
O1"—C2'—C3'—C4' | 72.8 (2) | C3"—O3"—C9"—O8" | 1.7 (5) |
C1'—C2'—C3'—C4' | −47.8 (2) | C3"—O3"—C9"—C10" | −179.4 (3) |
C9'—O4'—C4'—C3' | 129.7 (2) | C3"—O3"—C9"A—O8"A | 2 (2) |
C9'—O4'—C4'—C5' | −113.1 (2) | C3"—O3"—C9"A—C10A | −176.8 (10) |
O3'—C3'—C4'—O4' | −69.0 (2) | C4"—O4"—C11"—O9" | 13.9 (3) |
C2'—C3'—C4'—O4' | 169.62 (16) | C4"—O4"—C11"—C12" | −164.8 (2) |
O3'—C3'—C4'—C5' | 174.90 (16) | C6"—O6"—C13"—O10" | −5.4 (4) |
C2'—C3'—C4'—C5' | 53.5 (2) | C6"—O6"—C13"—C14" | 172.8 (2) |
C1'—O5'—C5'—C6' | −173.25 (18) |
Molecular Parameter | αMan(OAc)5, (I) | MeαMan(OAc)4, (II) | Man3(OAc)11, (III) |
Bond lengths (Å) | |||
rCC (endocyclic) | 1.524 ± 0.006 | 1.525 ± 0.005 | 1.523 ± 0.009 |
rC5,C6 | 1.508 ± 0.005 | 1.511 (2) | 1.500 ± 0.003 |
rC,Ob | 1.443 ± 0.004 | 1.441 ± 0.002 | 1.442 ± 0.006 |
rO,Ccar | 1.356 ± 0.008 | 1.353 ± 0.009 | 1.348 ± 0.008 |
rCcar,Ocar | 1.195 ± 0.007 | 1.198 ± 0.006 | 1.197 ± 0.01 |
rCcar,CMe | 1.496 ± 0.005 | 1.494 ± 0.001 | 1.500 ± 0.008 |
Bond angles (°) | |||
C5—O5—C1 | 114.2 ± 0.5 | 113.61 (12) | 113.9 ± 0.8 |
C—O—Ccar | 116.7 ± 1.6 | 116.7 ± 0.7 | 116.9 ± 0.8 |
O—Ccar—Ocar | 123.3 ± 0.7 | 123.4 ± 0.4 | 123.6 ± 0.7 |
O—Ccar—CMe | 111.0 ± 1.1 | 111.1 ± 0.3 | 110.6 ± 0.7 |
Ocar—Ccar—CMe | 125.9 ± 0.7 | 125.5 ± 0.5 | 125.9 ± 0.5 |
Torsion angles (°) | |||
C—O—Ccar—CMe | 180.1 ± 5.4 (trans) | 178.4 ± 7.4 (trans) | 180.0 ± 8.1 (trans) |
-65.5 (3) (gg) (R1) | |||
O5—C5—C6—O6 | 72.0 ± 7.7 (gt) | 65.16 (16) (gt) | 69.5 (2) (gt) (R2) |
60.5 (2) (gt) (R3) |
Notes: (a) values ± standard deviations; `car' denotes carbonyl C atoms and `Me' denotes methyl C atoms, in an O-acetyl side chain. (b) Only C—O bonds involved in O-acetylation. gg = gauche–gauche and gt = gauche–trans. |
Cx/Ox—Cy—Oy—Ccar torsion anglea | Torsion angle (°) | Deviation from idealized rotamerb (°) |
(Ia) | ||
O5—C1—O1—C1car | 79.9 (3) | -40.1 |
C1—C2—O2—C2car | -127.8 (2) | -7.8 |
C2—C3—O3—C3car | -78.1 (3) | +41.9 |
C3—C4—O4—C4car | 115.8 (2) | -4.2 |
C5—C6—O6—C6car | 179.1 (2) | -0.9 |
(Ib) | ||
O5—C1—O1—C1car | 113.1 (3) | -6.9 |
C1—C2—O2—C2car | -133.0 (2) | -13.0 |
C3—C4—O4—C4car | 96.8 (2) | -23.2 |
C5—C6—O6—C6car | 165.2 (2) | -14.8 |
(Ic) | ||
O5—C1—O1—C1car | 79.7 (2) | -40.3 |
C1—C2—O2—C2car | -131.0 (2) | -11.0 |
C2—C3—O3—C3car | -128.7 (3) | -8.7 |
C3—C4—O4—C4car | 115.9 (2) | -4.1 |
C5—C6—O6—C6car | -178.52 (19) (181.48) | +1.5 |
(II) | ||
C1—C2—O2—C2car | -136.57 (14) | -16.6 |
C2—C3—O3—C3car | -78.87 (17) | +41.1 |
C3—C4—O4—C4car | 124.93 (15) | +4.9 |
C5—C6—O6—C6car | 138.41 (15) | -41.6 |
(III) (R1) | ||
O5—C1—O1—C1car | 79.9 (3) | -40.1 |
C1—C2—O2—C2car | -132.62 (19) | -12.6 |
C3—C4—O4—C4car | 127.6 (2) | +7.6 |
C5—C6—O6—C6car | -156.1 (2) (203.9) | +23.9 |
(III) (R2) | ||
C2—C3—O3—C3car | -73.0 (2) | +47.0 |
C3—C4—O4—C4car | 129.7 (2) | +9.7 |
C5–C6—O6—C6car | -172.2 (2) (187.8) | +7.8 |
(III) (R3) | ||
C1—C2—O2—C2car | -133.17 (19) | -13.2 |
C3—C4—O4—C4car | 130.7 (2) | +10.7 |
C5—C6—O6—C6car | 156.3 (2) (203.7) | +23.7 |
Notes: (a) subscript `car' denotes the carbonyl C atom in an O-acetyl side chain. (b) Idealized C—O torsion angles are as follows: O5—C1—O1—C1car = 120°, C1—C2—O2—C2car = -120°, C2—C3—O3—C3car = -120°, C3—C4—O4—C4car = 120°, and C5—C6—O6—C6car = 180°. Values were calculated as [observed value - idealized value]. Some values (noted in parentheses) were calculated against the positive rotation value. |
Compound | θ (°) | φ (°) | Q (Å) | q2 (Å) | q3 (Å) |
(Ia) | 4.2 (3) | 215 (4) | 0.555 (3) | 0.038 (3) | 0.554 (3) |
(Ib) | 5.6 (3) | 62 (3) | 0.523 (3) | 0.047 (3) | 0.521 (3) |
(Ic) | 6.5 (3) | 298 (2) | 0.553 (3) | 0.067 (3) | 0.550 (3) |
(II) | 4.82 (18) | 282 (2) | 0.5757 (17) | 0.0485 (18) | 0.5737 (17) |
(III) (R1)a | 0.6 (2) | 236 (7) | 0.553 (2) | 0.019 (2) | 0.553 (2) |
(III) (R2) | 8.1 (2) | 302.3 (15) | 0.562 (2) | 0.082 (2) | 0.557 (2) |
(III) (R3) | 10.2 (2) | 276.0 (2) | 0.581 (2) | 0.104 (2) | 0.572 (2) |
(IV)b | 1.2 | 286 | 0.557 | 0.0118 | 0.5569 |
(V) (R1) | 10.7 (3) | 100.1 (18) | 0.521 (3) | 0.097 (3) | 0.512 (3) |
(V) (R2) | 3.9 (3) | 199 (5) | 0.535 (3) | 0.036 (3) | 0.534 (3) |
Average | 5.6 ± 3.4 | 226 ± 84 |
Notes: (a) for definitions of residues R1–R3 in (III) and R1–R2 in (V), see structures (III) and (V) in the text. (b) Errors were not reported for structure (IV). |
Structural parametera | (Ia) | (Ib) | (Ic) |
Bond lengths (Å) | |||
C1—C2 | 1.522 (4) | 1.519 (4) | 1.523 (3) |
C2—C3 | 1.530 (3) | 1.516 (4) | 1.523 (3) |
C3—C4 | 1.522 (3) | 1.519 (3) | 1.520 (3) |
C4—C5 | 1.535 (4) | 1.533 (3) | 1.530 (3) |
C5—C6 | 1.508 (3) | 1.503 (3) | 1.512 (3) |
C1—O1 | 1.435 (4) | 1.448 (3) | 1.433 (3) |
C1—O5 | 1.395 (3) | 1.399 (3) | 1.404 (3) |
C2—O2 | 1.435 (3) | 1.440 (3) | 1.449 (3) |
C3—O3 | 1.437 (3) | 1.443 (3) | 1.443 (3) |
C4—O4 | 1.446 (3) | 1.442 (3) | 1.442 (3) |
C5—O5 | 1.439 (3) | 1.439 (3) | 1.440 (3) |
C6—O6 | 1.444 (3) | 1.446 (3) | 1.445 (3) |
O1—C1car | 1.370 (4) | 1.350 (4) | 1.364 (3) |
O2—C2car | 1.358 (3) | 1.363 (3) | 1.356 (3) |
O3—C3car | 1.363 (3) | disordered | 1.354 (4) |
O4—C4car | 1.357 (3) | 1.360 (3) | 1.350 (3) |
O6—C6car | 1.342 (3) | 1.344 (3) | 1.352 (3) |
C1car—O1car | 1.198 (4) | 1.177 (5) | 1.188 (4) |
C2car—O2car | 1.194 (4) | 1.199 (4) | 1.198 (4) |
C3car—O3car | 1.206 (4) | disordered | 1.193 (4) |
C4car—O4car | 1.202 (3) | 1.192 (4) | 1.195 (4) |
C6car—O6car | 1.205 (4) | 1.190 (4) | 1.196 (4) |
O1car—C1Me | 1.489 (5) | 1.494 (6) | 1.502 (4) |
O2car—C2Me | 1.495 (4) | 1.494 (4) | 1.498 (4) |
O3car—C3Me | 1.491 (4) | 1.491 (4) | 1.499 (5) |
O4car—C4Me | 1.494 (3) | 1.498 (4) | 1.499 (3) |
O6car—C6Me | 1.505 (4) | 1.489 (4) | 1.499 (4) |
Bond angles (°) | |||
C5—O5—C1 | 114.78 (19) | 114.0 (2) | 113.96 (18) |
C1—O1—C1car | 117.0 (2) | 118.6 (3) | 114.66 (19) |
C2—O2—C2car | 117.3 (2) | 115.9 (2) | 116.9 (2) |
C3—O3—C3car | 115.1 (2) | 118.9 (2) | 118.1 (2) |
C4—O4—C4car | 116.72 (19) | 118.64 (19) | 117.81 (19) |
C6—O6—C6car | 113.7 (2) | 115.0 (2) | 115.94 (19) |
O1—C1car—O1car | 122.6 (3) | 123.3 (4) | 123.0 (3) |
O2—C2car—O2car | 123.3 (3) | 123.6 (3) | 123.8 (3) |
O3—C3car—O3car | 122.4 (3) | disordered | 124.9 (3) |
O4—C4car—O4car | 123.2 (2) | 123.8 (3) | 122.8 (2) |
O6—C6car—O6car | 123.8 (3) | 122.9 (3) | 122.7 (2) |
O1—C1car—C1Me | 110.4 (3) | 111.1 (4) | 110.5 (2) |
O2—C2car—C2Me | 110.7 (2) | 110.8 (2) | 111.4 (2) |
O3—C3car—C3Me | 111.2 (3) | 113.7 (3) | 109.0 (3) |
O4—C4car—C4Me | 111.2 (2) | 109.6 (2) | 111.0 (2) |
O6—C6car—C6Me | 111.0 (3) | 112.5 (2) | 110.9 (2) |
O1car—C1car—C1Me | 126.9 (3) | 125.6 (4) | 126.5 (2) |
O2car—C2car—C2Me | 126.1 (2) | 125.6 (3) | 124.8 (3) |
O3car—C3car—C3Me | 126.4 (3) | disordered | 126.1 (3) |
O4car—C4car—C4Me | 125.6 (2) | 126.6 (3) | 126.2 (2) |
O6car—C6car—C6Me | 125.2 (3) | 124.6 (3) | 126.3 (3) |
Torsion angles (°) | |||
C1—C2—C3—C4 | -54.0 (3) | -50.5 (3) | -48.5 (3) |
C1—O5—C5—C4 | 57.1 (3) | 55.2 (3) | 62.5 (2) |
O5—C1—O1—C1car | 79.9 (3) | 113.1 (3) | 79.7 (2) |
C1—C2—O2—C2car | -127.8 (2) | -133.0 (2) | -131.0 (2) |
C2—C3—O3—C3car | -78.1 (3) | -112.0 (3) | -128.7 (3) |
C3—C4—O4—C4car | 115.8 (2) | 96.8 (2) | 115.9 (2) |
C5—C6—O6—C6car | 179.1 (2) | 165.2 (2) | -178.52 (19) |
C1—O1—C1car—C1Me | -170.0 (2) | 174.6 (3) | -176.5 (2) |
C2—O2—C2car—C2Me | 179.1 (2) | 175.4 (2) | 177.8 (2) |
C3—O3—C3car—C3Me | 170.9 (2) | -177.7 (3) | -178.4 (4) |
C4—O4—C4car—C4Me | 175.5 (2) | -179.5 (2) | -172.1 (2) |
C6—O6—C6car—C6Me | -174.2 (2) | 174.8 (3) | -178.6 (2) |
O5—C5—C6—O6 | 65.0 (2) (gt) | 70.8 (3) (gt) | 80.3 (2) (gt) |
Notes: (a) subscripts `car' denote carbonyl C atoms and subscripts `Me' denote methyl C atoms in an O-acetyl side chain. gg = gauche–trans. |
Structural parametera | Redetermined structure | Reported structureb |
Bond lengths (Å) | ||
C1—C2 | 1.524 (2) | 1.522 |
C2—C3 | 1.528 (2) | 1.531 |
C3—C4 | 1.517 (2) | 1.513 |
C4—C5 | 1.529 (2) | 1.531 |
C5—C6 | 1.511 (2) | 1.508 |
C1—O1 | 1.400 (2) | 1.402 |
C1—O5 | 1.418 (2) | 1.417 |
C2—O2 | 1.440 (2) | 1.441 |
C3—O3 | 1.4394 (19) | 1.439 |
C4—O4 | 1.4418 (19) | 1.444 |
C5—O5 | 1.4362 (19) | 1.438 |
C6—O6 | 1.443 (2) | 1.445 |
O1—CH3 | 1.431 (2) | 1.433 |
O2—C2car | 1.360 (2) | 1.360 |
O3—C3car | 1.355 (2) | 1.351 |
O4—C4car | 1.357 (2) | 1.360 |
O6—C6car | 1.339 (2) | 1.341 |
C2car—O2car | 1.201 (2) | 1.201 |
C3car—O3car | 1.205 (2) | 1.204 |
C4car—O4car | 1.191 (3) | 1.191 |
C6car—O6car | 1.195 (2) | 1.197 |
C2car—C2Me | 1.494 (2) | 1.498 |
C3car—C3Me | 1.494 (2) | 1.499 |
C4car—C4Me | 1.492 (3) | 1.490 |
C6car—C6Me | 1.494 (2) | 1.493 |
Bond angles (°) | ||
C5—O5—C1 | 113.61 (12) | 113.53 |
C1—O1—CH3 | 112.64 (13) | 112.59 |
C2—O2—C2car | 116.10 (13) | 116.03 |
C3—O3—C3car | 116.21 (13) | 116.40 |
C4—O4—C4car | 116.91 (13) | 116.71 |
C6—O6—C6car | 117.69 (14) | 117.49 |
O2—C2car—O2car | 123.34 (16) | 123.32 |
O3—C3car—O3car | 123.48 (16) | 123.54 |
O4—C4car—O4car | 122.91 (17) | 123.09 |
O6—C6car—O6car | 123.75 (17) | 123.92 |
O2—C2car—C2Me | 111.38 (14) | 111.29 |
O3—C3car—C3Me | 110.58 (15) | 110.75 |
O4—C4car—C4Me | 111.14 (15) | 110.85 |
O6—C6car—C6Me | 111.23 (15) | 111.12 |
O2car—C2car—C2Me | 125.28 (16) | 125.38 |
O3car—C3car—C3Me | 125.93 (16) | 125.70 |
O4car—C4car—C4Me | 125.94 (18) | 126.05 |
O6car—C6car—C6Me | 125.01 (17) | 124.96 |
Torsion angles (°) | ||
C1—C2—C3—C4 | -52.21 (17) | -52.06 |
C1—O5—C5—C4 | 62.50 (17) | 62.02 |
O5—C1—O1—CH3 | 63.15 (18) | 63.08 |
C1—C2—O2—C2car | -136.57 (14) | -136.66 |
C2—C3—O3—C3car | -78.87 (17) | -78.58 |
C3—C4—O4—C4car | 124.93 (15) | 125.25 |
C5—C6—O6—C6car | 138.41 (15) | 137.57 |
C2—O2—C2car—C2Me | 169.26 (14) | 168.68 |
C3—O3—C3car—C3Me | -179.18 (15) | -179.12 |
C4—O4—C4car—C4Me | -173.07 (14) | -173.23 |
C6—O6—C6car—C6Me | 176.78 (14) | 177.16 |
O5—C5—C6—O6 | 65.16 (16) (gt) | 64.94 (gt) |
Notes: (a) subscripts `car' denote carbonyl C atoms and subscripts `Me' denote methyl C atoms in an O-acetyl side chain. (b) Data taken from Szeleszczuk et al. (2017). gt = gauche–trans. |
Structural parametera | R1b | R2 | R3 |
Bond lengths (Å) | |||
C1—C2 | 1.521 (3) | 1.527 (3) | 1.528 (3) |
C2—C3 | 1.522 (3) | 1.532 (3) | 1.520 (3) |
C3—C4 | 1.507 (3) | 1.514 (3) | 1.511 (3) |
C4—C5 | 1.533 (3) | 1.528 (3) | 1.532 (3) |
C5—C6 | 1.500 (4) | 1.497 (3) | 1.503 (3) |
C1—O1 | 1.437 (3) | 1.417 (2) | 1.411 (3) |
C1—O5 | 1.394 (3) | 1.410 (3) | 1.417 (3) |
C2—O2 | 1.438 (3) | 1.429 (2) | 1.441 (3) |
C3—O3 | 1.436 (2) | 1.436 (2) | 1.438 (3) |
C4—O4 | 1.438 (3) | 1.447 (3) | 1.439 (3) |
C5—O5 | 1.439 (3) | 1.439 (3) | 1.442 (3) |
C6—O6 | 1.457 (4) | 1.448 (3) | 1.441 (3) |
O1—C1car | 1.354 (3) | ||
O2—C2car | 1.355 (3) | 1.363 (3) | |
O3—C3car | 1.341 (3) | disordered | |
O4—C4car | 1.347 (3) | 1.347 (3) | 1.349 (3) |
O6—C6car | 1.337 (4) | 1.337 (3) | 1.346 (3) |
C1car—O1car | 1.215 (4) | ||
C2car—O2car | 1.190 (4) | 1.191 (4) | |
C3car—O3car | 1.206 (3) | disordered | |
C4car—O4car | 1.194 (4) | 1.186 (4) | 1.201 (4) |
C6car—O6car | 1.210 (4) | 1.188 (4) | 1.189 (3) |
O1car—C1Me | 1.499 (4) | ||
O2car—C2Me | 1.502(4 | 1.495 (4) | |
O3car—C3Me | 1.493 (4) | 1.509 (6) | |
O4car—C4Me | 1.506 (4) | 1.494 (4) | 1.513 (4) |
O6car—C6Me | 1.487 (6) | 1.508 (4) | 1.496 (3) |
Bond angles (°) | |||
C5—O5—C1 | 114.59 (18) | 113.06 (15) | 113.99 (17) |
C1—O1—C1car | 116.6 (2) | ||
C2—O2—C2car | 117.88 (19) | 115.86 (19) | |
C3—O3—C3car | 116.73 (19) | disordered | |
C4—O4—C4car | 117.72 (19) | 118.31 (19) | 116.7 (2) |
C6—O6—C6car | 116.7 (3) | 116.1 (2) | 116.72 (17) |
O1—C1car—O1car | 123.1 (3) | ||
O2—C2car—O2car | 124.2 (2) | 124.0 (2) | |
O3—C3car—O3car | 122.6 (2) | 124.9 (3) | |
O4—C4car—O4car | 124.2 (3) | 122.8 (3) | 124.0 (2) |
O6—C6car—O6car | 122.8 (3) | 123.6 (3) | 123.3 (2) |
O1—C1car—C1Me | 110.5 (3) | ||
O2—C2car—C2Me | 109.5 (2) | 110.1 (2) | |
O3—C3car—C3Me | 111.9 (2) | disordered | |
O4—C4car—C4Me | 110.2 (2) | 110.3 (2) | 110.8 (3) |
O6—C6car—C6Me | 111.3 (3) | 110.6 (3) | 110.72 (19) |
O1car—C1car—C1Me | 126.3 (3) | ||
O2car—C2car-C2Me | 126.3 (3) | 125.8 (2) | |
O3car—C3car-C3Me | 125.5 (2) | disordered | |
O4car—C4car-C4Me | 125.6 (3) | 126.8 (3) | 125.2 (3) |
O6car—C6car-C6Me | 125.9 (3) | 125.8 (3) | 126.0 (2) |
C1"—O1"—C2' | 114.18 (17) | ||
C1'—O1'—C3 | 113.13 (15) | ||
Torsion angles (°) | |||
C1—C2—C3—C4 | –52.8 (2) | –47.7 (2) | –49.6 (2) |
C1—O5—C5—C4 | 58.0 (3) | 64.5 (2) | 63.9 (2) |
O5—C1—O1—C1car | 79.8 (3) | ||
C1—C2—O2—C2car | –132.42 (19) | –133.34 (19) | |
C2—C3—O3—C3car | –73.1 (2) | disordered | |
C3—C4—O4—C4car | 127.6 (2) | 129.7 (2) | 130.5 (2) |
C5—C6—O6—C6car | –155.8 (2) | –172.0 (2) | 156.2 (2) |
C1—O1—C1car—C1Me | –170.8 (3) | ||
C2—O2—C2car—C2Me | 174.93 (19) | 173.5 (2) | |
C3—O3—C3car—C3Me | 171.6 (2) | disordered | |
C4—O4—C4car—C4Me | –174.7 (2) | –177.2 (2) | –164.9 (2) |
C6—O6—C6car—C6Me | 173.2 (3) | –178.5 (2) | 172.9 (2) |
O5—C5—C6—O6 | –65.5 (3) (gg) | ||
O5'—C5'—C6'—O6' | 69.5 (2) (gt) | ||
O5"—C5"—C6"—O6" | 60.5 (2) (gt) | ||
C2"—C1"—O1"—C2' | –152.08 (16) | ||
C1"—O1"—C2'—C1' | –92.1 (2) | ||
C1"—O1"—C2'—C3' | 147.46 (16) | ||
C2'—C1'—O1'—C3 | –163.29 (17) | ||
C1'—O1'—C3—C2 | –126.53 (18) | ||
C1'—O1'—C3—C4 | 111.79 (19) |
Notes: (a) subscripts `car' denote carbonyl C atoms, and subscripts `Me' denote methyl C atoms in an O-acetyl side chain. (b) R1, R2 and R3 refer to the three Man residues in (III) [see structure (III) in text for assignments]. gg = gauche–gauche and gt = gauche–trans. |
Bond lengths (Å) | Bond lengths (Å) | ||
C1—C2 | 1.524 | C2—O2 | 1.415 |
C2—C3 | 1.529 | C3—O3 | 1.422 |
C3—C4 | 1.519 | C4—O4 | 1.430 |
C4—C5 | 1.529 | C5—O5 | 1.435 |
C5—C6 | 1.518 | C6—O6 | 1.413 |
C1—O1 | 1.400 | O1—CH3 | 1.423 |
C1—O5 | 1.415 | ||
Bond angles (°) | |||
C5—O5—C1 | 114.29 | C1—O1—CH3 | 113.91 |
Torsion angles (°) | |||
C1—C2—C3—C4 | -53.37 | ||
C1—O5—C5—C4 | 59.13 | ||
O5—C1—O1—CH3 | 60.51 | ||
O5—C5—C6—O6 | -65.10 (gg) |
Note: (a) data taken from Jeffrey et al. (1977). gg = gauche–gauche. |
Structural Parameter | R1a | R2 |
Bond lengths (Å) | ||
C1—C2 | 1.522 (1.522)b | 1.513 (1.520) |
C2—C3 | 1.520 (1.524) | 1.521 (1.525) |
C3—C4 | 1.517 (1.524) | 1.517 (1.517) |
C4—C5 | 1.525 (1.534) | 1.517 (1.536)c |
C5—C6 | 1.517 (1.521) | 1.517 (1.515) |
C1—O1 | 1.397 (1.408) | 1.403 (1.411) |
C1—O5 | 1.417 (1.413) | 1.411 (1.411) |
C2—O2 | 1.432 (1.439) | 1.430 (1.432) |
C3—O3 | 1.427 (1.423) | 1.416 (1.424) |
C4—O4 | 1.430 (1.438) | 1.431 (1.429) |
C5—O5 | 1.430 (1.436) | 1.447 (1.445) |
C6—O6 | 1.439 (1.434) | 1.425 (1.426) |
O1—CH3 | 1.428 (1.439) | |
Bond angles (°) | ||
C5—O5—C1 | 115.66 (115.57) | |
C5'—O5'—C1' | 115.65 (115.78) | |
C1'—O1'—C2 | 114.02 (113.78) | |
C1—O1—CH3 | 112.96 (112.29) | |
Torsion angles (°) | ||
C1—C2—C3—C4 | -54.22 (-53.86) | |
C1—O5—C5—C4 | 49.74 (50.34) | |
C1'—C2'—C3'—C4' | -53.72 (-54.39) | |
C1'—O5'—C5'—C4' | 54.73 (54.22) | |
C2—C1—O1—CH3 (φ) | -177.67 (-178.83) | |
O5—C1—O1—CH3 (φ) | 60.09 (59.17) | |
H1—C1—O1—CH3 (φ) | -53.92 (-61.61) | |
C2'—C1'—O1'—C2 (φ') | -172.08 (-172.26) | |
O5'—C1'—O1'—C2 (φ') | 64.24 (64.33) | |
H1'—C1'—O1'—C2 (φ') | -53.99 (-55.32) | |
C1'—O1'—C2—C1 (ψ') | -105.30 (-104.08) | |
C1'—O1'—C2—C3 (ψ') | 136.12 (136.62) | |
C1'—O1'—C2—H2 (ψ') | 14.89 (16.99) | |
O5—C5—C6—O6 | -54.76 (-54.30) (gg) | |
O5'—C5'—C6'—O6' | -67.43 (-66.88) (gg) |
Notes: (a) R1 and R2 refer to the two αManp residues in disaccharide (V); see structure (V) in the text for assignments. The primed atoms in R2 are identified as unprimed for the bond lengths to simplify the table. (b) Values in parentheses pertain to the new low temperature X-ray structure redetermination of (V) solved in this study. (c) Values shown in bold font are those showing large differences between the two structures. gg = gauche–gauche. |
1H NMR (600 MHz, CDCl3) |
δ: 2.01 (s, 3H), 2.05 (s, 6H), 2.08 (s, 3H), 2.10 (s, 3H), 2.12 (s, 3H), 2.13 (s, 3H), 2.14 (s, 3H), 2.16 (s, 6H), 2.23 (s, 3H), 3.91 (dd, J = 3.0, 2.1 Hz, 1H), 3.97 (m, 2H), 4.10 (dd, J = 12.6, 2.5 Hz, 1H), 4.11-4.24 (m, 6H), 4.26 (dd, J = 12.5, 5.1 Hz, 1H), 4.85 (d, J = 1.9 Hz, 1H), 5.13 (dd, J = 9.9, 3.1 Hz, 1H), 5.14 (d, J = 2.0 Hz, 1H), 5.26 (m, 2H), 5.30 (t, J = 10.0 Hz, 1H), 5.34 (t, J = 10.0 Hz, 2H), 5.39 (dd, J = 10.0, 3.3 Hz, 1H), 6.10 (d, J = 1.9 Hz, 1H) |
13C NMR (150 MHz, CDCl3) |
δ: 20.5, 20.6 (×2), 20.7, 20.7, 20.7 (×2), 20.7, 20.8, 20.8, 21.0, 62.0, 62.0, 62.5, 65.5, 66.3, 67.4, 68.3, 69.4, 69.4, 69.5, 69.5, 69.6, 70.5, 74.4, 77.9, 90.5, 99.6, 99.8, 167.8, 169.4 (×2), 169.5, 169.7, 169.8, 170.0, 170.2, 170.3, 170.6, 170.7. |