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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006857/bt6040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006857/bt6040Isup2.hkl
Contains datablock I

CCDC reference: 165669

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.

Comment top

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).

Experimental top

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.

Refinement top

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 top

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 top
[Figure 1] 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 top
Crystal data top
C28H38O19·C4H8O2Dx = 1.323 Mg m3
Mr = 766.69Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4833 reflections
a = 14.1406 (1) Åθ = 2.0–27.3°
b = 15.2215 (1) ŵ = 0.11 mm1
c = 17.8879 (2) ÅT = 293 K
V = 3850.21 (6) Å3Prism, colourless
Z = 40.4 × 0.3 × 0.2 mm
F(000) = 1624
Data collection top
Enraf-Nonius KappaCCD area-detector
diffractometer
4833 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode3409 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.0°
ϕ and ω scans to fill Ewald sphereh = 1718
Absorption correction: multi-scan
using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995)
k = 1818
Tmin = 0.957, Tmax = 0.978l = 2323
41400 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0569P)2]
where P = (Fo2 + 2Fc2)/3
4833 reflections(Δ/σ)max = 0.002
488 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C28H38O19·C4H8O2V = 3850.21 (6) Å3
Mr = 766.69Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 14.1406 (1) ŵ = 0.11 mm1
b = 15.2215 (1) ÅT = 293 K
c = 17.8879 (2) Å0.4 × 0.3 × 0.2 mm
Data collection top
Enraf-Nonius KappaCCD area-detector
diffractometer
4833 independent reflections
Absorption correction: multi-scan
using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995)
3409 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.978Rint = 0.084
41400 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.00Δρmax = 0.54 e Å3
4833 reflectionsΔρmin = 0.34 e Å3
488 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.24761 (12)0.50657 (11)0.69258 (8)0.0198 (4)
O20.35494 (11)0.49212 (12)0.82096 (9)0.0240 (4)
O30.37678 (14)0.62401 (14)0.87406 (12)0.0396 (5)
O40.23379 (13)0.37729 (11)0.89904 (9)0.0233 (4)
O50.12059 (11)0.56622 (12)0.75952 (9)0.0219 (4)
O60.29369 (16)0.25888 (13)0.84058 (11)0.0447 (6)
O70.05778 (13)0.34412 (11)0.81954 (9)0.0248 (4)
O80.00552 (17)0.34988 (14)0.93443 (11)0.0511 (6)
O90.07106 (13)0.54943 (13)0.70486 (11)0.0350 (5)
O100.1617 (2)0.43297 (16)0.67996 (14)0.0618 (7)
C10.21990 (16)0.55554 (16)0.75623 (13)0.0188 (5)
H10.25010.61340.75470.023*
C20.25432 (17)0.50563 (17)0.82486 (13)0.0201 (5)
H20.23910.53930.87000.024*
C30.20747 (17)0.41666 (16)0.82907 (13)0.0190 (5)
H30.22740.37960.78710.023*
C40.10119 (17)0.42917 (17)0.82853 (13)0.0208 (5)
H40.08040.45610.87550.025*
C50.06921 (17)0.48476 (16)0.76238 (14)0.0220 (5)
H50.07840.45210.71570.026*
C60.03384 (18)0.5084 (2)0.77136 (16)0.0324 (7)
H6A0.06990.45560.78210.039*
H6B0.04090.54820.81340.039*
C70.40958 (19)0.55695 (19)0.84991 (14)0.0264 (6)
C80.5118 (2)0.5332 (2)0.84639 (17)0.0361 (7)
H8A0.54750.57290.87710.043*
H8B0.53340.53730.79560.043*
H8C0.52020.47420.86420.043*
C90.27802 (19)0.29815 (18)0.89714 (15)0.0280 (6)
C100.3050 (2)0.27072 (19)0.97357 (15)0.0390 (7)
H10A0.32690.21110.97260.047*
H10B0.25110.27511.00600.047*
H10C0.35450.30820.99180.047*
C110.00421 (19)0.31286 (18)0.87611 (15)0.0282 (6)
C120.0418 (2)0.2294 (2)0.85412 (19)0.0472 (9)
H12A0.10570.24090.83890.057*
H12B0.04190.18980.89590.057*
H12C0.00760.20350.81330.057*
C130.1377 (2)0.5059 (2)0.66567 (17)0.0371 (7)
C140.1751 (3)0.5612 (2)0.60460 (19)0.0553 (9)
H14A0.21520.60610.62510.066*
H14B0.21100.52550.57070.066*
H14C0.12350.58810.57830.066*
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)
H1'0.19290.59410.62400.026*
C2'0.24842 (17)0.49390 (17)0.56036 (13)0.0204 (5)
H2'0.24220.52760.51390.025*
C3'0.33764 (17)0.43937 (16)0.55684 (13)0.0205 (5)
H3'0.33810.39610.59740.025*
C4'0.42535 (17)0.49699 (16)0.56123 (13)0.0216 (5)
H4'0.43500.52850.51410.026*
C5'0.41790 (17)0.56145 (17)0.62628 (14)0.0222 (5)
H5'0.42060.52930.67370.027*
C6'0.4969 (2)0.62841 (19)0.62355 (15)0.0308 (6)
H6'A0.55690.59910.61530.037*
H6'B0.48630.66920.58270.037*
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'A0.04620.41150.52880.048*
H8'B0.01010.36770.59450.048*
H8'C0.03340.34270.51150.048*
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)
H10D0.34940.21200.40550.040*
H10E0.39320.29850.37290.040*
H10F0.28400.29220.38690.040*
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)
H12D0.68110.34350.51260.045*
H12E0.60580.29390.56120.045*
H12F0.65940.37540.59410.045*
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)
H14D0.45920.85320.77160.079*
H14E0.56350.81860.77480.079*
H14F0.48060.75970.80430.079*
O110.74712 (16)0.56486 (15)0.82116 (12)0.0490 (6)
O120.71925 (17)0.55070 (17)0.94391 (12)0.0548 (6)
C150.8210 (3)0.7094 (2)0.8284 (2)0.0550 (9)
H15A0.85710.69800.78400.066*
H15B0.85700.69190.87150.066*
H15C0.80700.77100.83150.066*
C160.7312 (2)0.6585 (2)0.82579 (19)0.0456 (8)
H16A0.69450.67120.87030.055*
H16B0.69470.67720.78280.055*
C170.7390 (2)0.5199 (2)0.8839 (2)0.0459 (8)
C180.7531 (3)0.4221 (3)0.8711 (2)0.0674 (11)
H18A0.69820.39070.88800.081*
H18B0.80750.40240.89840.081*
H18C0.76230.41120.81870.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0229 (9)0.0183 (8)0.0182 (8)0.0004 (8)0.0047 (7)0.0010 (7)
O20.0195 (9)0.0256 (9)0.0268 (9)0.0002 (8)0.0012 (7)0.0016 (8)
O30.0302 (11)0.0328 (12)0.0557 (13)0.0046 (10)0.0040 (10)0.0127 (10)
O40.0304 (10)0.0220 (9)0.0176 (9)0.0040 (8)0.0001 (7)0.0009 (7)
O50.0191 (9)0.0234 (9)0.0231 (9)0.0002 (7)0.0021 (7)0.0014 (7)
O60.0684 (16)0.0346 (12)0.0312 (11)0.0202 (11)0.0044 (10)0.0064 (9)
O70.0273 (10)0.0218 (9)0.0253 (9)0.0078 (8)0.0038 (8)0.0042 (7)
O80.0765 (17)0.0455 (13)0.0314 (11)0.0313 (13)0.0196 (12)0.0086 (10)
O90.0269 (11)0.0413 (12)0.0368 (11)0.0018 (10)0.0098 (8)0.0084 (9)
O100.0861 (19)0.0407 (14)0.0587 (15)0.0096 (15)0.0148 (14)0.0125 (12)
C10.0177 (13)0.0180 (13)0.0207 (12)0.0004 (10)0.0021 (9)0.0033 (10)
C20.0169 (12)0.0237 (13)0.0196 (12)0.0001 (11)0.0027 (10)0.0001 (10)
C30.0222 (13)0.0212 (13)0.0136 (12)0.0007 (10)0.0000 (9)0.0018 (10)
C40.0226 (13)0.0209 (13)0.0190 (13)0.0036 (11)0.0019 (10)0.0017 (11)
C50.0192 (13)0.0256 (14)0.0212 (13)0.0014 (11)0.0008 (10)0.0009 (11)
C60.0207 (14)0.0432 (17)0.0332 (15)0.0006 (13)0.0005 (11)0.0113 (13)
C70.0229 (14)0.0286 (16)0.0278 (14)0.0065 (13)0.0015 (11)0.0028 (12)
C80.0217 (15)0.0430 (18)0.0437 (17)0.0053 (13)0.0048 (12)0.0053 (14)
C90.0291 (15)0.0237 (14)0.0313 (15)0.0002 (12)0.0019 (11)0.0022 (12)
C100.056 (2)0.0273 (16)0.0335 (16)0.0078 (14)0.0074 (14)0.0041 (13)
C110.0314 (15)0.0257 (15)0.0276 (14)0.0065 (12)0.0042 (12)0.0006 (12)
C120.051 (2)0.0342 (18)0.057 (2)0.0168 (16)0.0208 (16)0.0109 (16)
C130.0327 (16)0.0384 (19)0.0403 (17)0.0089 (15)0.0049 (12)0.0122 (14)
C140.058 (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)
O110.0480 (13)0.0491 (14)0.0499 (13)0.0045 (12)0.0118 (11)0.0089 (11)
O120.0546 (15)0.0721 (18)0.0376 (13)0.0106 (13)0.0039 (11)0.0091 (12)
C150.062 (2)0.047 (2)0.056 (2)0.0005 (19)0.0007 (18)0.0093 (17)
C160.050 (2)0.0387 (18)0.0486 (19)0.0053 (16)0.0095 (16)0.0055 (15)
C170.0206 (16)0.062 (2)0.055 (2)0.0041 (15)0.0004 (14)0.0170 (18)
C180.052 (2)0.056 (2)0.094 (3)0.007 (2)0.021 (2)0.028 (2)
Geometric parameters (Å, º) top
O1—C1'1.416 (3)O3'—C7'1.197 (3)
O1—C11.416 (3)O4'—C9'1.359 (3)
O2—C71.356 (3)O4'—C3'1.445 (3)
O2—C21.439 (3)O5'—C1'1.410 (3)
O3—C71.201 (3)O5'—C5'1.439 (3)
O4—C91.358 (3)O6'—C9'1.202 (3)
O4—C31.437 (3)O7'—C11'1.361 (3)
O5—C11.415 (3)O7'—C4'1.444 (3)
O5—C51.438 (3)O8'—C11'1.196 (3)
O6—C91.196 (3)O9'—C13'1.193 (4)
O7—C111.351 (3)O10'—C13'1.351 (4)
O7—C41.442 (3)O10'—C6'1.440 (3)
O8—C111.194 (3)C1'—C2'1.516 (3)
O9—C131.348 (4)C2'—C3'1.512 (4)
O9—C61.443 (3)C3'—C4'1.521 (3)
O10—C131.189 (4)C4'—C5'1.526 (3)
C1—C21.523 (3)C5'—C6'1.513 (4)
C2—C31.510 (3)C7'—C8'1.486 (4)
C3—C41.515 (3)C9'—C10'1.483 (4)
C4—C51.523 (3)C11'—C12'1.488 (4)
C5—C61.510 (4)C13'—C14'1.491 (4)
C7—C81.491 (4)O11—C171.319 (4)
C9—C101.479 (4)O11—C161.445 (4)
C11—C121.480 (4)O12—C171.204 (4)
C13—C141.477 (4)C15—C161.488 (5)
O2'—C7'1.359 (3)C17—C181.520 (5)
O2'—C2'1.445 (3)
C1'—O1—C1113.36 (17)C1'—O5'—C5'113.63 (17)
C7—O2—C2116.1 (2)C11'—O7'—C4'118.20 (19)
C9—O4—C3117.88 (19)C13'—O10'—C6'117.6 (2)
C1—O5—C5113.81 (19)O5'—C1'—O1111.50 (19)
C11—O7—C4118.13 (19)O5'—C1'—C2'109.38 (19)
C13—O9—C6118.1 (2)O1—C1'—C2'108.04 (19)
O5—C1—O1111.63 (18)O2'—C2'—C3'106.5 (2)
O5—C1—C2109.93 (18)O2'—C2'—C1'111.13 (19)
O1—C1—C2107.28 (19)C3'—C2'—C1'111.9 (2)
O2—C2—C3107.9 (2)O4'—C3'—C2'105.02 (18)
O2—C2—C1110.37 (18)O4'—C3'—C4'110.23 (19)
C3—C2—C1110.32 (19)C2'—C3'—C4'111.2 (2)
O4—C3—C2107.69 (18)O7'—C4'—C3'109.31 (19)
O4—C3—C4108.36 (18)O7'—C4'—C5'105.03 (18)
C2—C3—C4108.8 (2)C3'—C4'—C5'110.72 (19)
O7—C4—C3108.1 (2)O5'—C5'—C6'106.5 (2)
O7—C4—C5106.60 (19)O5'—C5'—C4'110.50 (19)
C3—C4—C5111.7 (2)C6'—C5'—C4'111.0 (2)
O5—C5—C6106.6 (2)O10'—C6'—C5'108.7 (2)
O5—C5—C4110.89 (19)O3'—C7'—O2'122.9 (3)
C6—C5—C4109.7 (2)O3'—C7'—C8'126.6 (3)
O9—C6—C5111.6 (2)O2'—C7'—C8'110.5 (3)
O3—C7—O2122.4 (2)O6'—C9'—O4'122.6 (2)
O3—C7—C8126.5 (3)O6'—C9'—C10'127.1 (2)
O2—C7—C8111.1 (2)O4'—C9'—C10'110.3 (2)
O6—C9—O4123.4 (2)O8'—C11'—O7'123.1 (2)
O6—C9—C10126.4 (2)O8'—C11'—C12'127.2 (3)
O4—C9—C10110.2 (2)O7'—C11'—C12'109.7 (2)
O8—C11—O7123.6 (2)O9'—C13'—O10'123.3 (3)
O8—C11—C12125.9 (3)O9'—C13'—C14'126.0 (3)
O7—C11—C12110.5 (2)O10'—C13'—C14'110.7 (3)
O10—C13—O9123.1 (3)C17—O11—C16116.7 (3)
O10—C13—C14126.1 (3)O11—C16—C15112.5 (3)
O9—C13—C14110.8 (3)O12—C17—O11125.2 (3)
C7'—O2'—C2'116.5 (2)O12—C17—C18123.1 (3)
C9'—O4'—C3'118.56 (19)O11—C17—C18111.6 (3)
C5—O5—C1—O159.3 (2)C1—O1—C1'—O5'77.7 (2)
C5—O5—C1—C259.6 (2)C1—O1—C1'—C2'162.07 (19)
C1'—O1—C1—O579.5 (2)C7'—O2'—C2'—C3'155.0 (2)
C1'—O1—C1—C2160.06 (19)C7'—O2'—C2'—C1'83.0 (2)
C7—O2—C2—C3151.17 (19)O5'—C1'—C2'—O2'174.74 (18)
C7—O2—C2—C188.2 (2)O1—C1'—C2'—O2'53.2 (3)
O5—C1—C2—O2178.29 (19)O5'—C1'—C2'—C3'55.8 (3)
O1—C1—C2—O256.7 (2)O1—C1'—C2'—C3'65.7 (2)
O5—C1—C2—C359.1 (2)C9'—O4'—C3'—C2'137.4 (2)
O1—C1—C2—C362.5 (2)C9'—O4'—C3'—C4'102.8 (2)
C9—O4—C3—C2122.3 (2)O2'—C2'—C3'—O4'68.3 (2)
C9—O4—C3—C4120.1 (2)C1'—C2'—C3'—O4'170.08 (18)
O2—C2—C3—O466.1 (2)O2'—C2'—C3'—C4'172.47 (19)
C1—C2—C3—O4173.23 (18)C1'—C2'—C3'—C4'50.9 (3)
O2—C2—C3—C4176.64 (18)C11'—O7'—C4'—C3'91.2 (2)
C1—C2—C3—C456.0 (2)C11'—O7'—C4'—C5'149.9 (2)
C11—O7—C4—C3115.5 (2)O4'—C3'—C4'—O7'79.6 (2)
C11—O7—C4—C5124.3 (2)C2'—C3'—C4'—O7'164.37 (18)
O4—C3—C4—O772.9 (2)O4'—C3'—C4'—C5'165.19 (19)
C2—C3—C4—O7170.24 (17)C2'—C3'—C4'—C5'49.1 (3)
O4—C3—C4—C5170.13 (18)C1'—O5'—C5'—C6'178.4 (2)
C2—C3—C4—C553.3 (3)C1'—O5'—C5'—C4'61.0 (2)
C1—O5—C5—C6175.94 (19)O7'—C4'—C5'—O5'170.84 (18)
C1—O5—C5—C456.6 (2)C3'—C4'—C5'—O5'52.9 (2)
O7—C4—C5—O5170.68 (17)O7'—C4'—C5'—C6'71.3 (3)
C3—C4—C5—O552.9 (3)C3'—C4'—C5'—C6'170.8 (2)
O7—C4—C5—C671.8 (3)C13'—O10'—C6'—C5'120.9 (3)
C3—C4—C5—C6170.3 (2)O5'—C5'—C6'—O10'71.9 (3)
C13—O9—C6—C5113.7 (3)C4'—C5'—C6'—O10'167.8 (2)
O5—C5—C6—O968.7 (3)C2'—O2'—C7'—O3'4.3 (4)
C4—C5—C6—O9171.2 (2)C2'—O2'—C7'—C8'175.2 (2)
C2—O2—C7—O33.7 (3)C3'—O4'—C9'—O6'4.4 (4)
C2—O2—C7—C8176.9 (2)C3'—O4'—C9'—C10'177.2 (2)
C3—O4—C9—O62.1 (4)C4'—O7'—C11'—O8'3.7 (4)
C3—O4—C9—C10176.4 (2)C4'—O7'—C11'—C12'175.5 (2)
C4—O7—C11—O83.7 (4)C6'—O10'—C13'—O9'3.0 (5)
C4—O7—C11—C12174.5 (2)C6'—O10'—C13'—C14'175.7 (3)
C6—O9—C13—O106.0 (4)C17—O11—C16—C15100.1 (3)
C6—O9—C13—C14173.7 (3)C16—O11—C17—O120.3 (5)
C5'—O5'—C1'—O157.8 (2)C16—O11—C17—C18177.5 (3)
C5'—O5'—C1'—C2'61.6 (2)

Experimental details

Crystal data
Chemical formulaC28H38O19·C4H8O2
Mr766.69
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)14.1406 (1), 15.2215 (1), 17.8879 (2)
V3)3850.21 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.4 × 0.3 × 0.2
Data collection
DiffractometerEnraf-Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995)
Tmin, Tmax0.957, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
41400, 4833, 3409
Rint0.084
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.096, 1.00
No. of reflections4833
No. of parameters488
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.34

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SIR97 (Altomare et al.,1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top
O1—C1'1.416 (3)O5—C51.438 (3)
O1—C11.416 (3)O5'—C1'1.410 (3)
O5—C11.415 (3)O5'—C5'1.439 (3)
C1'—O1—C1113.36 (17)O4'—C3'—C2'105.02 (18)
C1—O5—C5113.81 (19)O8'—C11'—C12'127.2 (3)
C1'—O5'—C5'113.63 (17)
 

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