α,α-Trehalose octa­acetate ethyl acetate solvate

All hydroxy groups on the parent compound, trehalose, have been substituted with acetate groups and the solvent of recrystallization, ethyl acetate, has been incorporated into the crystal lattice to give the title compound, C₂₈H₃₈O₁₉·C₄H₈O₂.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.096
• Data-to-parameter ratio = 9.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.47
         From the CIF: _reflns_number_total               4833
         Count of symmetry unique reflns         4892
         Completeness (_total/calc)             98.79%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

S1. Comment

Trehalose is implicated in the preservation of life without water (Branca et al., 1999) and it is used in certain drug formulations (Hatley & Blair, 1999). The role of hydrogen bonding in trehalose and its derivatives is of continuing interest (Clow et al., 2001). Polymorphic forms of α,α-trehalose octaacetate monohydrate have been reported previously (Park & Shin, 1993) and the crystal structure of sucrose octaacetate has been studied (Oliver & Strickland, 1984). We now report the crystal structure of the α,α-trehalose octaacetate ethyl acetate solvate, (I) and base the stereochemistry of the molecule on the known absolute stereochemistry of trehalose.

No hydrogen bonds are present in (I). The substitution at C1/C1' is α,α, with C1—O1 = C1'—O1 = 1.416 (3) Å and C1—O1—C1' = 113.4 (2)°. The absolute configuration is R at the carbons C1, C2, C4 and C5 (also at C1', C2', C4' and C5') and S at C3 and C3'. The two six-membered rings adopt chair conformations with puckering parameters (Cremer & Pople, 1975) calculated with PLATON (Spek, 1998) of Q = 0.549 (2) Å, θ = 4.5 (3)°, ø = 14 (3)° (primed atoms) and Q = 0.563 (2) Å, θ = 4.3 (3)° and ø = 106 (4)° (unprimed atoms).

S2. Experimental

The title compound was prepared by reacting anhydrous α,α-trehalose with acetic anhydride. Purification was achieved through a combination of column chromatography and recrystallization from methanol. Crystals for X-ray work were obtained by slow evaporation from ethyl acetate.

S3. Refinement

The H atoms were initially placed in calculated positions and thereafter allowed to ride on their attached atoms. Each H atom was given an equivalent isotropic displacement parameter 1.2 greater than their attached atom. The H atoms of the methyl groups were allowed to rotate about the local threefold axes to maximize the sum of the electron density at the calculated H-atom positions.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

Figures

Fig. 1. The atomic arrangement in the title molecule. Displacement ellipsoids are shown at the 50% probability level.

2,3,4,6-tetra-O-acetyl-1-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl) -α-D-glucopyranose ethyl acetate solvate

Crystal data

C28H38O19·C4H8O2	Dx = 1.323 Mg m^−3
Mr = 766.69	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4833 reflections
a = 14.1406 (1) Å	θ = 2.0–27.3°
b = 15.2215 (1) Å	µ = 0.11 mm^−1
c = 17.8879 (2) Å	T = 293 K
V = 3850.21 (6) Å^3	Prism, colourless
Z = 4	0.4 × 0.3 × 0.2 mm
F(000) = 1624

Data collection

Enraf-Nonius KappaCCD area-detector diffractometer	4833 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode	3409 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.0°
ϕ and ω scans to fill Ewald sphere	h = −17→18
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995)	k = −18→18
Tmin = 0.957, Tmax = 0.978	l = −23→23
41400 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0569P)^2] where P = (Fo^2 + 2Fc^2)/3
4833 reflections	(Δ/σ)max = 0.002
488 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.24761 (12)	0.50657 (11)	0.69258 (8)	0.0198 (4)
O2	0.35494 (11)	0.49212 (12)	0.82096 (9)	0.0240 (4)
O3	0.37678 (14)	0.62401 (14)	0.87406 (12)	0.0396 (5)
O4	0.23379 (13)	0.37729 (11)	0.89904 (9)	0.0233 (4)
O5	0.12059 (11)	0.56622 (12)	0.75952 (9)	0.0219 (4)
O6	0.29369 (16)	0.25888 (13)	0.84058 (11)	0.0447 (6)
O7	0.05778 (13)	0.34412 (11)	0.81954 (9)	0.0248 (4)
O8	−0.00552 (17)	0.34988 (14)	0.93443 (11)	0.0511 (6)
O9	−0.07106 (13)	0.54943 (13)	0.70486 (11)	0.0350 (5)
O10	−0.1617 (2)	0.43297 (16)	0.67996 (14)	0.0618 (7)
C1	0.21990 (16)	0.55554 (16)	0.75623 (13)	0.0188 (5)
H1	0.2501	0.6134	0.7547	0.023*
C2	0.25432 (17)	0.50563 (17)	0.82486 (13)	0.0201 (5)
H2	0.2391	0.5393	0.8700	0.024*
C3	0.20747 (17)	0.41666 (16)	0.82907 (13)	0.0190 (5)
H3	0.2274	0.3796	0.7871	0.023*
C4	0.10119 (17)	0.42917 (17)	0.82853 (13)	0.0208 (5)
H4	0.0804	0.4561	0.8755	0.025*
C5	0.06921 (17)	0.48476 (16)	0.76238 (14)	0.0220 (5)
H5	0.0784	0.4521	0.7157	0.026*
C6	−0.03384 (18)	0.5084 (2)	0.77136 (16)	0.0324 (7)
H6A	−0.0699	0.4556	0.7821	0.039*
H6B	−0.0409	0.5482	0.8134	0.039*
C7	0.40958 (19)	0.55695 (19)	0.84991 (14)	0.0264 (6)
C8	0.5118 (2)	0.5332 (2)	0.84639 (17)	0.0361 (7)
H8A	0.5475	0.5729	0.8771	0.043*
H8B	0.5334	0.5373	0.7956	0.043*
H8C	0.5202	0.4742	0.8642	0.043*
C9	0.27802 (19)	0.29815 (18)	0.89714 (15)	0.0280 (6)
C10	0.3050 (2)	0.27072 (19)	0.97357 (15)	0.0390 (7)
H10A	0.3269	0.2111	0.9726	0.047*
H10B	0.2511	0.2751	1.0060	0.047*
H10C	0.3545	0.3082	0.9918	0.047*
C11	0.00421 (19)	0.31286 (18)	0.87611 (15)	0.0282 (6)
C12	−0.0418 (2)	0.2294 (2)	0.85412 (19)	0.0472 (9)
H12A	−0.1057	0.2409	0.8389	0.057*
H12B	−0.0419	0.1898	0.8959	0.057*
H12C	−0.0076	0.2035	0.8133	0.057*
C13	−0.1377 (2)	0.5059 (2)	0.66567 (17)	0.0371 (7)
C14	−0.1751 (3)	0.5612 (2)	0.60460 (19)	0.0553 (9)
H14A	−0.2152	0.6061	0.6251	0.066*
H14B	−0.2110	0.5255	0.5707	0.066*
H14C	−0.1235	0.5881	0.5783	0.066*
O2'	0.17063 (12)	0.43271 (11)	0.56594 (9)	0.0247 (4)
O3'	0.07217 (15)	0.53484 (14)	0.51939 (13)	0.0420 (5)
O4'	0.33362 (13)	0.39523 (11)	0.48537 (9)	0.0232 (4)
O5'	0.33080 (12)	0.61010 (11)	0.62208 (9)	0.0232 (4)
O6'	0.38886 (16)	0.26963 (13)	0.53495 (11)	0.0417 (5)
O7'	0.50650 (12)	0.44301 (12)	0.57832 (9)	0.0253 (4)
O8'	0.54067 (14)	0.42584 (15)	0.45635 (10)	0.0412 (5)
O9'	0.4719 (2)	0.80295 (16)	0.63503 (14)	0.0659 (8)
O10'	0.49899 (14)	0.67524 (12)	0.69349 (9)	0.0324 (5)
C1'	0.24934 (18)	0.55685 (16)	0.62600 (13)	0.0215 (5)
H1'	0.1929	0.5941	0.6240	0.026*
C2'	0.24842 (17)	0.49390 (17)	0.56036 (13)	0.0204 (5)
H2'	0.2422	0.5276	0.5139	0.025*
C3'	0.33764 (17)	0.43937 (16)	0.55684 (13)	0.0205 (5)
H3'	0.3381	0.3961	0.5974	0.025*
C4'	0.42535 (17)	0.49699 (16)	0.56123 (13)	0.0216 (5)
H4'	0.4350	0.5285	0.5141	0.026*
C5'	0.41790 (17)	0.56145 (17)	0.62628 (14)	0.0222 (5)
H5'	0.4206	0.5293	0.6737	0.027*
C6'	0.4969 (2)	0.62841 (19)	0.62355 (15)	0.0308 (6)
H6'A	0.5569	0.5991	0.6153	0.037*
H6'B	0.4863	0.6692	0.5827	0.037*
C7'	0.08524 (19)	0.4614 (2)	0.54100 (14)	0.0283 (6)
C8'	0.0144 (2)	0.3895 (2)	0.54421 (16)	0.0398 (7)
H8'A	−0.0462	0.4115	0.5288	0.048*
H8'B	0.0101	0.3677	0.5945	0.048*
H8'C	0.0334	0.3427	0.5115	0.048*
C9'	0.35853 (18)	0.30908 (17)	0.48195 (15)	0.0255 (6)
C10'	0.3451 (2)	0.27493 (19)	0.40502 (15)	0.0334 (7)
H10D	0.3494	0.2120	0.4055	0.040*
H10E	0.3932	0.2985	0.3729	0.040*
H10F	0.2840	0.2922	0.3869	0.040*
C11'	0.55735 (19)	0.40935 (18)	0.52039 (16)	0.0294 (6)
C12'	0.6326 (2)	0.3503 (2)	0.54965 (16)	0.0374 (7)
H12D	0.6811	0.3435	0.5126	0.045*
H12E	0.6058	0.2939	0.5612	0.045*
H12F	0.6594	0.3754	0.5941	0.045*
C13'	0.4874 (2)	0.7633 (2)	0.69125 (18)	0.0431 (8)
C14'	0.4987 (3)	0.8022 (2)	0.76725 (19)	0.0660 (11)
H14D	0.4592	0.8532	0.7716	0.079*
H14E	0.5635	0.8186	0.7748	0.079*
H14F	0.4806	0.7597	0.8043	0.079*
O11	0.74712 (16)	0.56486 (15)	0.82116 (12)	0.0490 (6)
O12	0.71925 (17)	0.55070 (17)	0.94391 (12)	0.0548 (6)
C15	0.8210 (3)	0.7094 (2)	0.8284 (2)	0.0550 (9)
H15A	0.8571	0.6980	0.7840	0.066*
H15B	0.8570	0.6919	0.8715	0.066*
H15C	0.8070	0.7710	0.8315	0.066*
C16	0.7312 (2)	0.6585 (2)	0.82579 (19)	0.0456 (8)
H16A	0.6945	0.6712	0.8703	0.055*
H16B	0.6947	0.6772	0.7828	0.055*
C17	0.7390 (2)	0.5199 (2)	0.8839 (2)	0.0459 (8)
C18	0.7531 (3)	0.4221 (3)	0.8711 (2)	0.0674 (11)
H18A	0.6982	0.3907	0.8880	0.081*
H18B	0.8075	0.4024	0.8984	0.081*
H18C	0.7623	0.4112	0.8187	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0229 (9)	0.0183 (8)	0.0182 (8)	−0.0004 (8)	0.0047 (7)	0.0010 (7)
O2	0.0195 (9)	0.0256 (9)	0.0268 (9)	−0.0002 (8)	−0.0012 (7)	−0.0016 (8)
O3	0.0302 (11)	0.0328 (12)	0.0557 (13)	−0.0046 (10)	−0.0040 (10)	−0.0127 (10)
O4	0.0304 (10)	0.0220 (9)	0.0176 (9)	0.0040 (8)	−0.0001 (7)	0.0009 (7)
O5	0.0191 (9)	0.0234 (9)	0.0231 (9)	−0.0002 (7)	0.0021 (7)	0.0014 (7)
O6	0.0684 (16)	0.0346 (12)	0.0312 (11)	0.0202 (11)	−0.0044 (10)	−0.0064 (9)
O7	0.0273 (10)	0.0218 (9)	0.0253 (9)	−0.0078 (8)	0.0038 (8)	−0.0042 (7)
O8	0.0765 (17)	0.0455 (13)	0.0314 (11)	−0.0313 (13)	0.0196 (12)	−0.0086 (10)
O9	0.0269 (11)	0.0413 (12)	0.0368 (11)	−0.0018 (10)	−0.0098 (8)	0.0084 (9)
O10	0.0861 (19)	0.0407 (14)	0.0587 (15)	−0.0096 (15)	−0.0148 (14)	−0.0125 (12)
C1	0.0177 (13)	0.0180 (13)	0.0207 (12)	0.0004 (10)	0.0021 (9)	−0.0033 (10)
C2	0.0169 (12)	0.0237 (13)	0.0196 (12)	0.0001 (11)	0.0027 (10)	0.0001 (10)
C3	0.0222 (13)	0.0212 (13)	0.0136 (12)	0.0007 (10)	0.0000 (9)	0.0018 (10)
C4	0.0226 (13)	0.0209 (13)	0.0190 (13)	−0.0036 (11)	0.0019 (10)	−0.0017 (11)
C5	0.0192 (13)	0.0256 (14)	0.0212 (13)	−0.0014 (11)	0.0008 (10)	0.0009 (11)
C6	0.0207 (14)	0.0432 (17)	0.0332 (15)	−0.0006 (13)	−0.0005 (11)	0.0113 (13)
C7	0.0229 (14)	0.0286 (16)	0.0278 (14)	−0.0065 (13)	−0.0015 (11)	0.0028 (12)
C8	0.0217 (15)	0.0430 (18)	0.0437 (17)	−0.0053 (13)	−0.0048 (12)	0.0053 (14)
C9	0.0291 (15)	0.0237 (14)	0.0313 (15)	0.0002 (12)	−0.0019 (11)	0.0022 (12)
C10	0.056 (2)	0.0273 (16)	0.0335 (16)	0.0078 (14)	−0.0074 (14)	0.0041 (13)
C11	0.0314 (15)	0.0257 (15)	0.0276 (14)	−0.0065 (12)	0.0042 (12)	0.0006 (12)
C12	0.051 (2)	0.0342 (18)	0.057 (2)	−0.0168 (16)	0.0208 (16)	−0.0109 (16)
C13	0.0327 (16)	0.0384 (19)	0.0403 (17)	0.0089 (15)	−0.0049 (12)	−0.0122 (14)
C14	0.058 (2)	0.055 (2)	0.052 (2)	0.016 (2)	−0.0237 (17)	−0.0106 (17)
O2'	0.0228 (9)	0.0245 (9)	0.0268 (9)	−0.0045 (8)	0.0000 (7)	−0.0001 (8)
O3'	0.0297 (12)	0.0381 (13)	0.0581 (14)	0.0002 (10)	−0.0094 (10)	0.0038 (11)
O4'	0.0306 (10)	0.0178 (9)	0.0212 (9)	0.0034 (8)	−0.0006 (8)	−0.0019 (7)
O5'	0.0254 (9)	0.0201 (9)	0.0242 (9)	−0.0027 (8)	0.0032 (8)	0.0012 (7)
O6'	0.0623 (15)	0.0266 (11)	0.0363 (12)	0.0119 (10)	−0.0011 (10)	0.0025 (9)
O7'	0.0227 (9)	0.0291 (10)	0.0241 (9)	0.0024 (8)	0.0009 (7)	−0.0005 (8)
O8'	0.0406 (12)	0.0567 (14)	0.0263 (11)	0.0167 (11)	0.0079 (9)	0.0025 (10)
O9'	0.108 (2)	0.0369 (14)	0.0532 (15)	0.0125 (14)	−0.0084 (15)	0.0014 (12)
O10'	0.0407 (12)	0.0288 (11)	0.0276 (10)	−0.0099 (9)	0.0002 (8)	−0.0051 (8)
C1'	0.0208 (13)	0.0201 (13)	0.0237 (12)	0.0018 (11)	0.0009 (11)	0.0029 (10)
C2'	0.0201 (13)	0.0215 (13)	0.0197 (12)	−0.0007 (11)	0.0020 (10)	0.0036 (10)
C3'	0.0262 (13)	0.0206 (13)	0.0148 (11)	0.0006 (12)	−0.0009 (10)	0.0004 (10)
C4'	0.0232 (13)	0.0215 (13)	0.0201 (13)	0.0026 (12)	0.0022 (10)	0.0017 (11)
C5'	0.0210 (13)	0.0230 (13)	0.0225 (13)	−0.0013 (11)	0.0026 (10)	0.0028 (11)
C6'	0.0323 (16)	0.0331 (16)	0.0268 (14)	−0.0083 (13)	0.0043 (12)	−0.0074 (12)
C7'	0.0226 (15)	0.0369 (18)	0.0254 (15)	−0.0014 (13)	0.0008 (11)	−0.0056 (12)
C8'	0.0323 (17)	0.0478 (19)	0.0393 (17)	−0.0096 (15)	0.0021 (13)	−0.0054 (14)
C9'	0.0262 (15)	0.0204 (14)	0.0299 (14)	0.0019 (11)	0.0039 (11)	−0.0003 (12)
C10'	0.0386 (17)	0.0276 (15)	0.0339 (15)	0.0025 (14)	0.0014 (13)	−0.0080 (12)
C11'	0.0262 (15)	0.0308 (15)	0.0313 (16)	0.0000 (12)	0.0082 (12)	−0.0001 (12)
C12'	0.0315 (16)	0.0411 (18)	0.0397 (17)	0.0104 (14)	0.0058 (13)	0.0020 (14)
C13'	0.052 (2)	0.0328 (18)	0.0445 (19)	−0.0065 (16)	0.0037 (15)	−0.0057 (15)
C14'	0.102 (3)	0.046 (2)	0.051 (2)	−0.012 (2)	0.008 (2)	−0.0194 (17)
O11	0.0480 (13)	0.0491 (14)	0.0499 (13)	0.0045 (12)	0.0118 (11)	0.0089 (11)
O12	0.0546 (15)	0.0721 (18)	0.0376 (13)	−0.0106 (13)	−0.0039 (11)	0.0091 (12)
C15	0.062 (2)	0.047 (2)	0.056 (2)	0.0005 (19)	0.0007 (18)	0.0093 (17)
C16	0.050 (2)	0.0387 (18)	0.0486 (19)	0.0053 (16)	0.0095 (16)	0.0055 (15)
C17	0.0206 (16)	0.062 (2)	0.055 (2)	−0.0041 (15)	−0.0004 (14)	0.0170 (18)
C18	0.052 (2)	0.056 (2)	0.094 (3)	0.007 (2)	0.021 (2)	0.028 (2)

Geometric parameters (Å, º)

O1—C1'	1.416 (3)	O3'—C7'	1.197 (3)
O1—C1	1.416 (3)	O4'—C9'	1.359 (3)
O2—C7	1.356 (3)	O4'—C3'	1.445 (3)
O2—C2	1.439 (3)	O5'—C1'	1.410 (3)
O3—C7	1.201 (3)	O5'—C5'	1.439 (3)
O4—C9	1.358 (3)	O6'—C9'	1.202 (3)
O4—C3	1.437 (3)	O7'—C11'	1.361 (3)
O5—C1	1.415 (3)	O7'—C4'	1.444 (3)
O5—C5	1.438 (3)	O8'—C11'	1.196 (3)
O6—C9	1.196 (3)	O9'—C13'	1.193 (4)
O7—C11	1.351 (3)	O10'—C13'	1.351 (4)
O7—C4	1.442 (3)	O10'—C6'	1.440 (3)
O8—C11	1.194 (3)	C1'—C2'	1.516 (3)
O9—C13	1.348 (4)	C2'—C3'	1.512 (4)
O9—C6	1.443 (3)	C3'—C4'	1.521 (3)
O10—C13	1.189 (4)	C4'—C5'	1.526 (3)
C1—C2	1.523 (3)	C5'—C6'	1.513 (4)
C2—C3	1.510 (3)	C7'—C8'	1.486 (4)
C3—C4	1.515 (3)	C9'—C10'	1.483 (4)
C4—C5	1.523 (3)	C11'—C12'	1.488 (4)
C5—C6	1.510 (4)	C13'—C14'	1.491 (4)
C7—C8	1.491 (4)	O11—C17	1.319 (4)
C9—C10	1.479 (4)	O11—C16	1.445 (4)
C11—C12	1.480 (4)	O12—C17	1.204 (4)
C13—C14	1.477 (4)	C15—C16	1.488 (5)
O2'—C7'	1.359 (3)	C17—C18	1.520 (5)
O2'—C2'	1.445 (3)
C1'—O1—C1	113.36 (17)	C1'—O5'—C5'	113.63 (17)
C7—O2—C2	116.1 (2)	C11'—O7'—C4'	118.20 (19)
C9—O4—C3	117.88 (19)	C13'—O10'—C6'	117.6 (2)
C1—O5—C5	113.81 (19)	O5'—C1'—O1	111.50 (19)
C11—O7—C4	118.13 (19)	O5'—C1'—C2'	109.38 (19)
C13—O9—C6	118.1 (2)	O1—C1'—C2'	108.04 (19)
O5—C1—O1	111.63 (18)	O2'—C2'—C3'	106.5 (2)
O5—C1—C2	109.93 (18)	O2'—C2'—C1'	111.13 (19)
O1—C1—C2	107.28 (19)	C3'—C2'—C1'	111.9 (2)
O2—C2—C3	107.9 (2)	O4'—C3'—C2'	105.02 (18)
O2—C2—C1	110.37 (18)	O4'—C3'—C4'	110.23 (19)
C3—C2—C1	110.32 (19)	C2'—C3'—C4'	111.2 (2)
O4—C3—C2	107.69 (18)	O7'—C4'—C3'	109.31 (19)
O4—C3—C4	108.36 (18)	O7'—C4'—C5'	105.03 (18)
C2—C3—C4	108.8 (2)	C3'—C4'—C5'	110.72 (19)
O7—C4—C3	108.1 (2)	O5'—C5'—C6'	106.5 (2)
O7—C4—C5	106.60 (19)	O5'—C5'—C4'	110.50 (19)
C3—C4—C5	111.7 (2)	C6'—C5'—C4'	111.0 (2)
O5—C5—C6	106.6 (2)	O10'—C6'—C5'	108.7 (2)
O5—C5—C4	110.89 (19)	O3'—C7'—O2'	122.9 (3)
C6—C5—C4	109.7 (2)	O3'—C7'—C8'	126.6 (3)
O9—C6—C5	111.6 (2)	O2'—C7'—C8'	110.5 (3)
O3—C7—O2	122.4 (2)	O6'—C9'—O4'	122.6 (2)
O3—C7—C8	126.5 (3)	O6'—C9'—C10'	127.1 (2)
O2—C7—C8	111.1 (2)	O4'—C9'—C10'	110.3 (2)
O6—C9—O4	123.4 (2)	O8'—C11'—O7'	123.1 (2)
O6—C9—C10	126.4 (2)	O8'—C11'—C12'	127.2 (3)
O4—C9—C10	110.2 (2)	O7'—C11'—C12'	109.7 (2)
O8—C11—O7	123.6 (2)	O9'—C13'—O10'	123.3 (3)
O8—C11—C12	125.9 (3)	O9'—C13'—C14'	126.0 (3)
O7—C11—C12	110.5 (2)	O10'—C13'—C14'	110.7 (3)
O10—C13—O9	123.1 (3)	C17—O11—C16	116.7 (3)
O10—C13—C14	126.1 (3)	O11—C16—C15	112.5 (3)
O9—C13—C14	110.8 (3)	O12—C17—O11	125.2 (3)
C7'—O2'—C2'	116.5 (2)	O12—C17—C18	123.1 (3)
C9'—O4'—C3'	118.56 (19)	O11—C17—C18	111.6 (3)
C5—O5—C1—O1	59.3 (2)	C1—O1—C1'—O5'	77.7 (2)
C5—O5—C1—C2	−59.6 (2)	C1—O1—C1'—C2'	−162.07 (19)
C1'—O1—C1—O5	79.5 (2)	C7'—O2'—C2'—C3'	−155.0 (2)
C1'—O1—C1—C2	−160.06 (19)	C7'—O2'—C2'—C1'	83.0 (2)
C7—O2—C2—C3	−151.17 (19)	O5'—C1'—C2'—O2'	174.74 (18)
C7—O2—C2—C1	88.2 (2)	O1—C1'—C2'—O2'	53.2 (3)
O5—C1—C2—O2	178.29 (19)	O5'—C1'—C2'—C3'	55.8 (3)
O1—C1—C2—O2	56.7 (2)	O1—C1'—C2'—C3'	−65.7 (2)
O5—C1—C2—C3	59.1 (2)	C9'—O4'—C3'—C2'	−137.4 (2)
O1—C1—C2—C3	−62.5 (2)	C9'—O4'—C3'—C4'	102.8 (2)
C9—O4—C3—C2	−122.3 (2)	O2'—C2'—C3'—O4'	68.3 (2)
C9—O4—C3—C4	120.1 (2)	C1'—C2'—C3'—O4'	−170.08 (18)
O2—C2—C3—O4	66.1 (2)	O2'—C2'—C3'—C4'	−172.47 (19)
C1—C2—C3—O4	−173.23 (18)	C1'—C2'—C3'—C4'	−50.9 (3)
O2—C2—C3—C4	−176.64 (18)	C11'—O7'—C4'—C3'	91.2 (2)
C1—C2—C3—C4	−56.0 (2)	C11'—O7'—C4'—C5'	−149.9 (2)
C11—O7—C4—C3	115.5 (2)	O4'—C3'—C4'—O7'	−79.6 (2)
C11—O7—C4—C5	−124.3 (2)	C2'—C3'—C4'—O7'	164.37 (18)
O4—C3—C4—O7	−72.9 (2)	O4'—C3'—C4'—C5'	165.19 (19)
C2—C3—C4—O7	170.24 (17)	C2'—C3'—C4'—C5'	49.1 (3)
O4—C3—C4—C5	170.13 (18)	C1'—O5'—C5'—C6'	−178.4 (2)
C2—C3—C4—C5	53.3 (3)	C1'—O5'—C5'—C4'	61.0 (2)
C1—O5—C5—C6	175.94 (19)	O7'—C4'—C5'—O5'	−170.84 (18)
C1—O5—C5—C4	56.6 (2)	C3'—C4'—C5'—O5'	−52.9 (2)
O7—C4—C5—O5	−170.68 (17)	O7'—C4'—C5'—C6'	71.3 (3)
C3—C4—C5—O5	−52.9 (3)	C3'—C4'—C5'—C6'	−170.8 (2)
O7—C4—C5—C6	71.8 (3)	C13'—O10'—C6'—C5'	−120.9 (3)
C3—C4—C5—C6	−170.3 (2)	O5'—C5'—C6'—O10'	71.9 (3)
C13—O9—C6—C5	113.7 (3)	C4'—C5'—C6'—O10'	−167.8 (2)
O5—C5—C6—O9	68.7 (3)	C2'—O2'—C7'—O3'	−4.3 (4)
C4—C5—C6—O9	−171.2 (2)	C2'—O2'—C7'—C8'	175.2 (2)
C2—O2—C7—O3	−3.7 (3)	C3'—O4'—C9'—O6'	−4.4 (4)
C2—O2—C7—C8	176.9 (2)	C3'—O4'—C9'—C10'	177.2 (2)
C3—O4—C9—O6	−2.1 (4)	C4'—O7'—C11'—O8'	3.7 (4)
C3—O4—C9—C10	176.4 (2)	C4'—O7'—C11'—C12'	−175.5 (2)
C4—O7—C11—O8	−3.7 (4)	C6'—O10'—C13'—O9'	3.0 (5)
C4—O7—C11—C12	174.5 (2)	C6'—O10'—C13'—C14'	−175.7 (3)
C6—O9—C13—O10	−6.0 (4)	C17—O11—C16—C15	100.1 (3)
C6—O9—C13—C14	173.7 (3)	C16—O11—C17—O12	0.3 (5)
C5'—O5'—C1'—O1	57.8 (2)	C16—O11—C17—C18	177.5 (3)
C5'—O5'—C1'—C2'	−61.6 (2)