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A low-temperature structure of ginkgolide A monohydrate, (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-3-(1,1-dimethylethyl)-hexa­hydro-4,7b-di­hydroxy-8-methyl-9H-1,7a-epoxymethano-1H,6aH-cyclo­penta­[c]­furo­[2,3-b]­furo­[3′,2′:3,4]­cyclopenta­[1,2-d]­furan-5,9,12(4H)-trione monohydrate, C20H24O9·H2O, obtained from Mo Kα data, is a factor of three more precise than the previous room-temperature determination. A refinement of the ginkgolide A monohydrate structure with Cu Kα data has allowed the assignment of the absolute configuration of the series of compounds. Ginkgolide C sesquihydrate, (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11S,11aR)-3-(1,1-di­methyl­ethyl)-hexa­hydro-2,4,7b,11-tetrahydroxy-8-methyl-9H-1,7a-epoxy­methano-1H,6aH-cyclopenta­[c]­furo­[2,3-b]­furo­[3′,2′:3,4]­cyclo­penta­[1,2-d]­furan-5,9,12(4H)-trione sesquihydrate, C20H24O11·1.5H2O, has two independent diterpene mol­ecules, both of which exhibit intramolecular hydrogen bonding between OH groups. Ginkgolide J dihydrate, (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-3-(1,1-di­methyl­ethyl)-hexa­hydro-2,4,7b-tri­hydroxy-8-methyl-9H-1,7a-epoxy­methano-1H,6aH-cyclo­penta­[c]­furo­[2,3-b]furo[3′,2′:3,4]­cyclo­penta­[1,2-d]­furan-5,9,12(4H)-trione dihydrate, C20H24O10·2H2O, has the same basic skeleton as the other ginkgolides, with its three OH groups having the same configurations as those in ginkgolide C. The conformations of the six five-membered rings are quite similar across ­ginkgolides A–C and J, except for the A and F rings of ginkgolide A.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102000689/bk1627sup1.cif
Contains datablocks global, I, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102000689/bk1627Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102000689/bk1627IIIsup3.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102000689/bk1627IVsup4.hkl
Contains datablock IV

txt

Text file https://doi.org/10.1107/S0108270102000689/bk1627sup5.cif
CIF for Cu refinement of ginkgolide A monohydrate

txt

Text file https://doi.org/10.1107/S0108270102000689/bk1627sup6.hkl
Structure factors for Cu refinement of ginkgolide A monohydrate

CCDC references: 183038; 183039; 183040

Comment top

The highly oxygenated diterpene trilactone-type caged molecules ginkgolide A, B, C and J were isolated from standardized extracts of Ginkgo biloba L. and were characterized by detailed high-field two-dimensional NMR studies. They are the major biochemical markers of Ginkgo biloba, which is considered an important vascular and neurological botanical and displays potent antagonistic activity against platelet-activating factor (PAF, PAF/acether, AGEPC) (Braquet, 1988; Braquet & Godfroid, 1986; Van Beek et al., 1998).

Out of five reported ginkgolides (Roumestand et al., 1989; Van Beek & Lankhorst, 1996; Weinges et al., 1987), the relative stereochemistries of ginkgolide A, B and C were previously determined by X-ray crystallography (Dupont et al., 1986; Sakabe et al., 1967; Sbit et al., 1987) in a study of the monohydrates of (I) and (II), and the ethanol 1.5-hydrate of (III). In order to prove conclusively the configurations of all 11 asymmetric centers of ginkgolide J, (IV), and especially to ascertain how it correlates with other ginkgolides [(I) and (III)], crystal structure determinations were undertaken. Crystallization from undried solvents yielded hydrates, namely ginkgolide A monohydrate (C20H24O9·H2O), ginkgolide C sesquihydrate (C20H24O11·1.5H2O), and ginkgolide J dihydrate (C20H24O10·2H2O), which also allowed direct determination of their comparative caged configurations. The structures reported herein are in agreement with the tentative assignments using NMR methods.

Our low-temperature determination of ginkgolide A monohydrate, (I)·H2O, with Mo Kα data confirms the earlier results of Sbit et al. (1987) and represents a substantial improvement in precision over their room-temperature structure. We have also measured room-temperature data with Cu Kα radiation at 296 K, and refinement using 3776 reflections (1439 Friedel pairs) yielded R = 0.028 and a Flack (1983) parameter of -0.02 (12). We have adopted this absolute structure for all three compounds reported herein, and it is consistent with the absolute configuration reported by Sakabe et al. (1967) for the p-bromobenzoate ester at C3. Their absolute configuration, determined from the diethanol solvate, was somewhat in doubt because of a rather high R value (0.190) from visually estimated film data with no absorption correction. Our room-temperature cell dimensions for the monohydrate are a = 8.992 (2), b = 12.438 (2), c = 17.819 (3) Å and V = 1992.9 (6) Å2, based on 25 reflections having 22.8 < θ < 43.1°, measured on an Enraf–Nonius CAD-4 diffractometer. The results of the Cu Kα refinement have been deposited as supplementary data.

Our low-temperature determination of the structure of ginkgolide C as the sesquihydrate, (III)·1.5H2O, represents an increase in precision of a factor of four over that of Sbit et al. (1987) for the sesquihydrate monoethanol solvate at room temperature. For their structure, as well as ours, Z' = 2. In both independent molecules of our structure, there is an intramolecular hydrogen bond between OH groups O1 and O5, with O1 as donor. The conformations of all the OH groups agree well between the A and B molecules, despite the differences in intermolecular hydrogen bonding (Table 3). In the structure of Sbit et al., the intramolecular hydrogen bond is reported to have O5 as the donor and O1 as the acceptor, although they were unable to locate all hydroxy H atoms. In the present structure, there are three independent water molecules, two of which are disordered into pairs of sites. O2W occupies sites of occupancy 0.72 (3) and 0.28 (3), separated by 0.641 (17) Å, while O3W occupies sites of equal occupancy [0.494 (10) and 0.506 (10)], separated by 0.849 (4) Å. All five water sites accept hydrogen bonds from ginkgolide C molecules; hydrogen bonding between water molecules is less unambiguous, because of the inability to locate the water H atoms.

The structure of the trihydroxy compound ginkgolide J, (IV), for which no crystal structure has been previously reported, is shown in Fig. 3 as the dihydrate, i.e. (IV)·2H2O. The configurations of all the asymmetric centers in the basic ginkgolide skeleton are shown to agree with those of ginkgolides A, B, and C. The OH groups have been confirmed to lie at C3, C7, and C10, with the same configurations as the OH groups at those positions in ginkgolide C.

The conformations of the six five-membered rings (A—F in the Scheme) of the ginkgolide skeleton have been discussed by Dupont et al. (1986) and Sbit et al. (1987). They found that the skeleton was fairly rigid, with the conformations of rings B—E differing little in ginkgolides A, B, and C, while those of the A and F rings of ginkgolide A differed from the pattern. They suggested that the anomalous A– and F-ring conformations of ginkgolide A are related to hydrogen bonding, as ginkgolide A carries no OH group at C1, while ginkgolides B and C do. Our results for the endocyclic torsion angles of the five-membered rings are given in Table 1. We also note little variation (11° or less) across the entire spectrum of torsion angles, except for the A and F rings of ginkgolide A. Notably, the conformations of the A and F rings in ginkgolide J, which, like ginkgolide A, carries no OH group at C1, fits the normal pattern.

The hydrogen bonding to the two independent molecules in ginkgolide C sesquihydrate differs (Table 3), which allows direct observation of the conformational differences caused by differences in intermolecular hydrogen bonding. The differences in torsion angles (Table 1) are small, with the overall mean deviation among 30 pairs of torsion angles only 2.7°. The A ring shows the largest deviation, with a mean of 5.1°, with the other rings having mean deviations as follows: B 1.6, C 1.0, D 2.9, E 4.1, F 1.2°.

Experimental top

Ginkgolides A, B, C and J were isolated in large scale from standardized extract (Neutrasource Inc. San Carlos, CA) of Ginkgo biloba L. (Ginkgoaceae) using a sodium acetate-impregnated silica-gel chromatographic technique (van Beek & Lelyveld, 1997) with the combination of a preseparation by normal column chromatography. Ginkgolide A, (I), was recrystallized from methanol (MeOH) as plates [m.p. 583 K; [α]D -38 (c, 0.069, dioxane) and -56° (c, 0.06, MeOH)], Ginkgolide C, (III), was recrystallized as plates from acetone/n-hexane [m.p. 558 K; [α]D -16° (c, 0.055, dioxane)] and ginkgolide J, (IV), was recrystallized as needles from acetone/n-hexane [m.p. 563 K; [α]D +1.6° (c, 0.061, dioxane)]. The initial physical and NMR data recorded at 500 (1H) and 125 (13C) MHz using a Bruker Avance DRX-500 instrument, were in agreement with those reported in the literature (Roumestand et al., 1989; Van Beek & Lankhorst, 1996; Weinges et al., 1987).

Refinement top

Population parameters of the disordered water sites in ginkgolide C sesquihydrate were refined, with each pair (O2W/O2W' and O3W/O3W') constrained to sum to unity. H atoms were placed in calculated positions, with C—H bond distances in the range 0.96–1.00 Å and thereafter treated as riding. A torsional parameter was refined for each methyl group. OH and H2O H atoms were placed from difference maps and refined as follows: for ginkgolide A monohydrate and ginkgolide J dihydrate, hydroxy O—H distances were constrained to be 0.82 Å and torsional parameters were refined, while water H-atom positions were refined individually. For ginkgolide C sesquihydrate, hydroxy O—H distances were constrained to be 0.84 Å and torsional parameters were refined, while water H atoms could not be unambiguously placed. For all compounds, Uiso = 1.2Ueq of the attached atom (1.5 for methyl groups and H atoms on O atoms).

Computing details top

For all compounds, data collection: COLLECT (Nonius 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996). Software used to prepare material for publication: SHELXL97 for (I), (III); SHELXL97 (Sheldrick, 1997) for (IV).

Figures top
[Figure 1] Fig. 1. View of ginkgolide A monohydrate showing the atom-numbering scheme and ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. View of one of the two independent molecules of ginkgolide C sesquihydrate showing the atom-numbering scheme and ellipsoids at the 50% probability level.
[Figure 3] Fig. 3. View of ginkgolide J dihydrate showing the atom-numbering scheme and ellipsoids at the 50% probability level.
(I) (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS) 3- (1,1dimethylethyl)hexahydro-4,7 b-dihydroxy-8-methyl-9H-1,7a- (epoxymethano)-1H,6aH-cyclopenta[c]furo[2,3 b]furo[3',2':3,4] cyclopenta[1,2-d]furan-5,9,12(4H)-trione monohydrate top
Crystal data top
C20H24O9·H2ODx = 1.446 Mg m3
Mr = 426.41Melting point: 583 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 8.931 (2) ÅCell parameters from 19931 reflections
b = 12.338 (2) Åθ = 2.5–33.2°
c = 17.779 (3) ŵ = 0.12 mm1
V = 1959.2 (6) Å3T = 120 K
Z = 4Fragment, colorless
F(000) = 9040.48 × 0.37 × 0.35 mm
Data collection top
KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
3936 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 33.2°, θmin = 2.5°
ω scans with κ offsetsh = 1313
19931 measured reflectionsk = 1818
4144 independent reflectionsl = 2727
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0419P)2 + 0.373P]
where P = (Fo2 + 2Fc2)/3
4144 reflections(Δ/σ)max < 0.001
283 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C20H24O9·H2OV = 1959.2 (6) Å3
Mr = 426.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.931 (2) ŵ = 0.12 mm1
b = 12.338 (2) ÅT = 120 K
c = 17.779 (3) Å0.48 × 0.37 × 0.35 mm
Data collection top
KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
3936 reflections with I > 2σ(I)
19931 measured reflectionsRint = 0.017
4144 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.29 e Å3
4144 reflectionsΔρmin = 0.21 e Å3
283 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 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
O20.58578 (10)0.27144 (8)0.31825 (5)0.02002 (18)
H2O0.61260.21900.34520.030*
O30.24970 (10)0.41947 (7)0.27989 (5)0.01649 (16)
O40.41751 (11)0.23326 (9)0.16733 (5)0.02142 (19)
O50.04901 (11)0.11715 (7)0.30436 (5)0.01907 (17)
H5O0.12840.10010.32680.029*
O60.07587 (11)0.27195 (9)0.42798 (5)0.02288 (19)
O70.03324 (10)0.39217 (7)0.35017 (5)0.01712 (16)
O80.50061 (11)0.40372 (9)0.17777 (6)0.0236 (2)
O90.27240 (10)0.30683 (7)0.44388 (5)0.01737 (17)
O100.28594 (13)0.47482 (8)0.48987 (6)0.0244 (2)
C10.26641 (14)0.16387 (10)0.34871 (7)0.0164 (2)
H1A0.16820.15150.37310.020*
H1B0.31520.09280.34040.020*
C20.36437 (13)0.23569 (10)0.39779 (6)0.0156 (2)
H20.43450.19170.42930.019*
C30.44985 (13)0.31425 (10)0.34594 (7)0.0160 (2)
C40.34378 (13)0.32591 (9)0.27695 (6)0.01434 (19)
C50.24565 (13)0.22449 (9)0.27271 (6)0.01373 (18)
C60.30576 (14)0.16278 (10)0.20308 (7)0.0175 (2)
H60.34910.09080.21710.021*
C70.17387 (15)0.15090 (11)0.15005 (7)0.0191 (2)
H7A0.11200.08720.16360.023*
H7B0.20800.14320.09730.023*
C80.08596 (14)0.25680 (10)0.16095 (6)0.0156 (2)
H80.15230.31540.14090.019*
C90.08828 (12)0.27060 (9)0.24849 (6)0.01333 (18)
C100.04446 (13)0.22997 (10)0.29420 (6)0.01510 (19)
H100.13830.25250.26780.018*
C110.03200 (13)0.29514 (10)0.36653 (7)0.0163 (2)
C120.09822 (13)0.38938 (9)0.27503 (6)0.01452 (19)
H120.04250.43850.24010.017*
C130.43176 (13)0.32779 (11)0.20352 (7)0.0180 (2)
C140.46471 (14)0.41759 (10)0.39373 (7)0.0179 (2)
H140.45400.48380.36170.021*
C150.33331 (14)0.40665 (10)0.44711 (7)0.0182 (2)
C160.61053 (16)0.42162 (13)0.43927 (9)0.0270 (3)
H16A0.60730.48310.47410.041*
H16B0.69560.43010.40500.041*
H16C0.62180.35420.46780.041*
C170.06227 (15)0.26571 (11)0.11536 (7)0.0189 (2)
C180.17177 (17)0.17144 (12)0.12845 (8)0.0257 (3)
H18A0.20210.17020.18140.039*
H18B0.12260.10290.11570.039*
H18C0.26030.18120.09660.039*
C190.01925 (18)0.26524 (14)0.03146 (7)0.0282 (3)
H19A0.02530.19510.01840.042*
H19B0.05330.32310.02170.042*
H19C0.10900.27710.00080.042*
C200.14044 (16)0.37442 (11)0.13101 (8)0.0227 (2)
H20A0.22850.38130.09840.034*
H20B0.07090.43400.12080.034*
H20C0.17180.37720.18380.034*
O1W0.32204 (11)0.57887 (8)0.12744 (6)0.02132 (18)
H1W0.372 (3)0.5233 (17)0.1416 (12)0.032*
H2W0.301 (2)0.5633 (17)0.0835 (12)0.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0155 (4)0.0230 (4)0.0216 (4)0.0046 (4)0.0025 (3)0.0049 (4)
O30.0133 (4)0.0133 (3)0.0229 (4)0.0006 (3)0.0003 (3)0.0021 (3)
O40.0182 (4)0.0271 (5)0.0190 (4)0.0010 (4)0.0060 (3)0.0002 (4)
O50.0197 (4)0.0137 (3)0.0238 (4)0.0018 (3)0.0045 (3)0.0006 (3)
O60.0242 (4)0.0269 (5)0.0176 (4)0.0017 (4)0.0067 (3)0.0003 (4)
O70.0192 (4)0.0154 (4)0.0168 (3)0.0002 (3)0.0039 (3)0.0022 (3)
O80.0178 (4)0.0277 (5)0.0252 (4)0.0012 (4)0.0049 (3)0.0101 (4)
O90.0179 (4)0.0184 (4)0.0158 (3)0.0007 (3)0.0015 (3)0.0011 (3)
O100.0306 (5)0.0213 (4)0.0212 (4)0.0029 (4)0.0015 (4)0.0025 (4)
C10.0179 (5)0.0143 (5)0.0169 (4)0.0005 (4)0.0000 (4)0.0028 (4)
C20.0160 (5)0.0162 (5)0.0147 (4)0.0013 (4)0.0010 (4)0.0023 (4)
C30.0138 (4)0.0172 (5)0.0171 (5)0.0014 (4)0.0002 (4)0.0023 (4)
C40.0140 (4)0.0144 (4)0.0146 (4)0.0007 (4)0.0016 (4)0.0023 (4)
C50.0139 (4)0.0133 (4)0.0140 (4)0.0010 (4)0.0021 (4)0.0008 (4)
C60.0177 (5)0.0176 (5)0.0173 (5)0.0038 (4)0.0034 (4)0.0005 (4)
C70.0215 (5)0.0192 (5)0.0165 (5)0.0027 (5)0.0012 (4)0.0030 (4)
C80.0168 (5)0.0169 (5)0.0131 (4)0.0008 (4)0.0004 (4)0.0002 (4)
C90.0134 (4)0.0130 (4)0.0136 (4)0.0011 (4)0.0014 (4)0.0005 (4)
C100.0154 (5)0.0143 (4)0.0156 (4)0.0003 (4)0.0019 (4)0.0006 (4)
C110.0142 (5)0.0166 (5)0.0181 (5)0.0008 (4)0.0023 (4)0.0002 (4)
C120.0143 (4)0.0139 (4)0.0154 (4)0.0007 (4)0.0011 (4)0.0006 (4)
C130.0133 (4)0.0230 (5)0.0179 (5)0.0033 (4)0.0020 (4)0.0049 (4)
C140.0178 (5)0.0172 (5)0.0188 (5)0.0017 (4)0.0001 (4)0.0004 (4)
C150.0187 (5)0.0195 (5)0.0165 (5)0.0014 (4)0.0024 (4)0.0013 (4)
C160.0213 (6)0.0284 (7)0.0314 (7)0.0029 (5)0.0064 (5)0.0035 (6)
C170.0205 (5)0.0198 (5)0.0164 (5)0.0001 (5)0.0026 (4)0.0007 (4)
C180.0268 (6)0.0251 (6)0.0253 (6)0.0063 (5)0.0068 (5)0.0002 (5)
C190.0327 (7)0.0359 (7)0.0159 (5)0.0036 (7)0.0035 (5)0.0004 (5)
C200.0209 (6)0.0221 (6)0.0252 (6)0.0034 (5)0.0056 (5)0.0007 (5)
O1W0.0223 (4)0.0192 (4)0.0224 (4)0.0011 (4)0.0016 (4)0.0011 (4)
Geometric parameters (Å, º) top
O2—C31.413 (2)C7—H7A0.9900
O2—H2O0.8400C7—H7B0.9900
O3—C121.406 (2)C8—C171.556 (2)
O3—C41.429 (2)C8—C91.566 (2)
O4—C131.338 (2)C8—H81.0000
O4—C61.469 (2)C9—C101.522 (2)
O5—C101.404 (2)C9—C121.542 (2)
O5—H5O0.8400C10—C111.521 (2)
O6—C111.196 (2)C10—H101.0000
O7—C111.363 (2)C12—H121.0000
O7—C121.457 (2)C14—C151.515 (2)
O8—C131.210 (2)C14—C161.534 (2)
O9—C151.348 (2)C14—H141.0000
O9—C21.455 (2)C16—H16A0.9800
O10—C151.210 (2)C16—H16B0.9800
C1—C21.521 (2)C16—H16C0.9800
C1—C51.555 (2)C17—C181.537 (2)
C1—H1A0.9900C17—C201.538 (2)
C1—H1B0.9900C17—C191.540 (2)
C2—C31.540 (2)C18—H18A0.9800
C2—H21.0000C18—H18B0.9800
C3—C141.538 (2)C18—H18C0.9800
C3—C41.556 (2)C19—H19A0.9800
C4—C131.524 (2)C19—H19B0.9800
C4—C51.530 (2)C19—H19C0.9800
C5—C61.549 (2)C20—H20A0.9800
C5—C91.576 (2)C20—H20B0.9800
C6—C71.516 (2)C20—H20C0.9800
C6—H61.0000O1W—H1W0.86 (2)
C7—C81.537 (2)O1W—H2W0.83 (2)
C3—O2—H2O109.5C8—C9—C5104.13 (9)
C12—O3—C4110.52 (9)O5—C10—C11114.68 (10)
C13—O4—C6111.89 (9)O5—C10—C9114.69 (10)
C10—O5—H5O109.5C11—C10—C9102.73 (9)
C11—O7—C12110.20 (9)O5—C10—H10108.1
C15—O9—C2110.34 (9)C11—C10—H10108.1
C2—C1—C5106.67 (9)C9—C10—H10108.1
C2—C1—H1A110.4O6—C11—O7123.06 (11)
C5—C1—H1A110.4O6—C11—C10128.49 (11)
C2—C1—H1B110.4O7—C11—C10108.38 (10)
C5—C1—H1B110.4O3—C12—O7108.71 (9)
H1A—C1—H1B108.6O3—C12—C9108.98 (9)
O9—C2—C1110.49 (10)O7—C12—C9106.26 (9)
O9—C2—C3103.72 (9)O3—C12—H12110.9
C1—C2—C3107.97 (9)O7—C12—H12110.9
O9—C2—H2111.5C9—C12—H12110.9
C1—C2—H2111.5O8—C13—O4122.76 (12)
C3—C2—H2111.5O8—C13—C4126.71 (12)
O2—C3—C14115.37 (10)O4—C13—C4110.46 (10)
O2—C3—C2113.54 (10)C15—C14—C16109.25 (10)
C14—C3—C2103.53 (9)C15—C14—C3101.85 (10)
O2—C3—C4106.43 (9)C16—C14—C3113.06 (11)
C14—C3—C4114.28 (10)C15—C14—H14110.8
C2—C3—C4103.18 (9)C16—C14—H14110.8
O3—C4—C13108.80 (9)C3—C14—H14110.8
O3—C4—C5109.01 (9)O10—C15—O9121.40 (12)
C13—C4—C5105.41 (9)O10—C15—C14127.04 (12)
O3—C4—C3113.81 (9)O9—C15—C14111.54 (10)
C13—C4—C3111.26 (9)C14—C16—H16A109.5
C5—C4—C3108.18 (9)C14—C16—H16B109.5
C4—C5—C6104.05 (9)H16A—C16—H16B109.5
C4—C5—C1106.40 (9)C14—C16—H16C109.5
C6—C5—C1114.61 (9)H16A—C16—H16C109.5
C4—C5—C9103.25 (9)H16B—C16—H16C109.5
C6—C5—C9105.55 (9)C18—C17—C20110.10 (11)
C1—C5—C9121.14 (9)C18—C17—C19107.61 (11)
O4—C6—C7108.43 (10)C20—C17—C19106.97 (11)
O4—C6—C5106.87 (10)C18—C17—C8114.14 (10)
C7—C6—C5105.98 (9)C20—C17—C8110.71 (10)
O4—C6—H6111.8C19—C17—C8106.97 (11)
C7—C6—H6111.8C17—C18—H18A109.5
C5—C6—H6111.8C17—C18—H18B109.5
C6—C7—C8103.68 (10)H18A—C18—H18B109.5
C6—C7—H7A111.0C17—C18—H18C109.5
C8—C7—H7A111.0H18A—C18—H18C109.5
C6—C7—H7B111.0H18B—C18—H18C109.5
C8—C7—H7B111.0C17—C19—H19A109.5
H7A—C7—H7B109.0C17—C19—H19B109.5
C7—C8—C17115.41 (10)H19A—C19—H19B109.5
C7—C8—C9102.18 (9)C17—C19—H19C109.5
C17—C8—C9121.42 (10)H19A—C19—H19C109.5
C7—C8—H8105.5H19B—C19—H19C109.5
C17—C8—H8105.5C17—C20—H20A109.5
C9—C8—H8105.5C17—C20—H20B109.5
C10—C9—C12101.22 (9)H20A—C20—H20B109.5
C10—C9—C8118.98 (10)C17—C20—H20C109.5
C12—C9—C8114.09 (9)H20A—C20—H20C109.5
C10—C9—C5115.45 (9)H20B—C20—H20C109.5
C12—C9—C5102.01 (9)H1W—O1W—H2W102.1 (19)
C15—O9—C2—C1139.48 (10)C4—C5—C9—C1223.49 (10)
C15—O9—C2—C323.99 (12)C6—C5—C9—C12132.43 (9)
C5—C1—C2—O992.01 (11)C1—C5—C9—C1295.26 (11)
C5—C1—C2—C320.79 (12)C4—C5—C9—C895.44 (10)
O9—C2—C3—O2155.81 (9)C6—C5—C9—C813.49 (11)
C1—C2—C3—O286.93 (12)C1—C5—C9—C8145.80 (10)
O9—C2—C3—C1429.98 (11)C12—C9—C10—O5157.45 (10)
C1—C2—C3—C14147.23 (10)C8—C9—C10—O576.71 (13)
O9—C2—C3—C489.42 (10)C5—C9—C10—O548.22 (14)
C1—C2—C3—C427.84 (12)C12—C9—C10—C1132.36 (11)
C12—O3—C4—C13112.18 (10)C8—C9—C10—C11158.20 (10)
C12—O3—C4—C52.29 (12)C5—C9—C10—C1176.87 (12)
C12—O3—C4—C3123.14 (10)C12—O7—C11—O6169.98 (12)
O2—C3—C4—O3143.58 (9)C12—O7—C11—C1013.07 (13)
C14—C3—C4—O315.03 (14)O5—C10—C11—O628.67 (19)
C2—C3—C4—O396.64 (11)C9—C10—C11—O6153.76 (13)
O2—C3—C4—C1320.23 (13)O5—C10—C11—O7154.60 (10)
C14—C3—C4—C13108.32 (11)C9—C10—C11—O729.50 (12)
C2—C3—C4—C13140.01 (10)C4—O3—C12—O7101.34 (10)
O2—C3—C4—C595.11 (11)C4—O3—C12—C914.06 (12)
C14—C3—C4—C5136.35 (10)C11—O7—C12—O3125.77 (10)
C2—C3—C4—C524.67 (12)C11—O7—C12—C98.61 (12)
O3—C4—C5—C6126.92 (9)C10—C9—C12—O3142.97 (9)
C13—C4—C5—C610.27 (11)C8—C9—C12—O388.00 (12)
C3—C4—C5—C6108.84 (10)C5—C9—C12—O323.62 (11)
O3—C4—C5—C1111.67 (10)C10—C9—C12—O725.99 (11)
C13—C4—C5—C1131.68 (9)C8—C9—C12—O7155.02 (9)
C3—C4—C5—C112.57 (12)C5—C9—C12—O793.36 (10)
O3—C4—C5—C916.88 (11)C6—O4—C13—O8168.83 (11)
C13—C4—C5—C999.78 (10)C6—O4—C13—C48.17 (13)
C3—C4—C5—C9141.11 (9)O3—C4—C13—O848.26 (16)
C2—C1—C5—C44.88 (12)C5—C4—C13—O8165.05 (12)
C2—C1—C5—C6119.29 (11)C3—C4—C13—O877.91 (15)
C2—C1—C5—C9112.30 (11)O3—C4—C13—O4128.59 (10)
C13—O4—C6—C7112.67 (11)C5—C4—C13—O411.80 (13)
C13—O4—C6—C51.17 (13)C3—C4—C13—O4105.24 (11)
C4—C5—C6—O46.06 (12)O2—C3—C14—C15149.59 (10)
C1—C5—C6—O4121.83 (10)C2—C3—C14—C1524.93 (11)
C9—C5—C6—O4102.29 (10)C4—C3—C14—C1586.53 (11)
C4—C5—C6—C7121.56 (10)O2—C3—C14—C1632.50 (15)
C1—C5—C6—C7122.67 (11)C2—C3—C14—C1692.16 (12)
C9—C5—C6—C713.21 (12)C4—C3—C14—C16156.38 (11)
O4—C6—C7—C878.97 (11)C2—O9—C15—O10170.55 (12)
C5—C6—C7—C835.47 (12)C2—O9—C15—C147.87 (13)
C6—C7—C8—C17177.37 (10)C16—C14—C15—O1070.15 (17)
C6—C7—C8—C943.50 (12)C3—C14—C15—O10170.04 (13)
C7—C8—C9—C1095.57 (12)C16—C14—C15—O9108.16 (12)
C17—C8—C9—C1034.69 (16)C3—C14—C15—O911.65 (13)
C7—C8—C9—C12145.01 (10)C7—C8—C17—C1854.85 (14)
C17—C8—C9—C1284.73 (14)C9—C8—C17—C1869.48 (15)
C7—C8—C9—C534.67 (11)C7—C8—C17—C20179.74 (10)
C17—C8—C9—C5164.93 (10)C9—C8—C17—C2055.41 (15)
C4—C5—C9—C10132.25 (10)C7—C8—C17—C1964.05 (14)
C6—C5—C9—C10118.82 (11)C9—C8—C17—C19171.62 (11)
C1—C5—C9—C1013.49 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O1Wi0.841.892.694 (2)160
O5—H5O···O1Wii0.841.932.764 (2)172
O1W—H1W···O80.86 (2)1.98 (2)2.831 (2)175 (2)
O1W—H2W···O10iii0.83 (2)1.90 (2)2.711 (2)169 (2)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y1/2, z+1/2; (iii) x+1/2, y+1, z1/2.
(III) (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11S,11aR) 3-(1,1-dimethylethyl) hexahydro-2,4,7 b,11-tetrahydroxy-8-methyl-9H-1,7a-(epoxymethano)-1H,6aH– cyclopenta[c]furo[2,3 b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12 (4H)-trione sesquihydrate top
Crystal data top
C20H24O11·1.5H2ODx = 1.526 Mg m3
Mr = 467.42Melting point: 558 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.4945 (15) ÅCell parameters from 5587 reflections
b = 12.973 (3) Åθ = 2.5–29.6°
c = 20.934 (4) ŵ = 0.13 mm1
β = 91.00 (2)°T = 120 K
V = 2035.0 (7) Å3Prism, colorless
Z = 40.47 × 0.27 × 0.25 mm
F(000) = 988
Data collection top
KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
5752 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 29.6°, θmin = 2.7°
ω scans with κ offsetsh = 1010
22429 measured reflectionsk = 1813
5921 independent reflectionsl = 2929
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0549P)2 + 0.4304P]
where P = (Fo2 + 2Fc2)/3
5921 reflections(Δ/σ)max = 0.001
622 parametersΔρmax = 0.37 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C20H24O11·1.5H2OV = 2035.0 (7) Å3
Mr = 467.42Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.4945 (15) ŵ = 0.13 mm1
b = 12.973 (3) ÅT = 120 K
c = 20.934 (4) Å0.47 × 0.27 × 0.25 mm
β = 91.00 (2)°
Data collection top
KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
5752 reflections with I > 2σ(I)
22429 measured reflectionsRint = 0.019
5921 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0311 restraint
wR(F2) = 0.086H-atom parameters constrained
S = 1.05Δρmax = 0.37 e Å3
5921 reflectionsΔρmin = 0.18 e Å3
622 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 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*/UeqOcc. (<1)
O1A0.10445 (15)0.32753 (11)0.53160 (6)0.0182 (2)
H1HA0.08630.35370.49560.027*
O2A0.18859 (17)0.13714 (10)0.69354 (6)0.0183 (2)
H2HA0.28810.11640.70750.027*
O3A0.47719 (15)0.21528 (10)0.57649 (6)0.0149 (2)
O4A0.15237 (17)0.04164 (10)0.53658 (6)0.0174 (2)
O5A0.11116 (16)0.38425 (10)0.43266 (6)0.0179 (2)
H5HA0.10800.43120.40510.027*
O6A0.33504 (18)0.52395 (10)0.50839 (6)0.0204 (3)
O7A0.48890 (16)0.38203 (10)0.53639 (6)0.0164 (2)
O8A0.37947 (19)0.00138 (10)0.60183 (6)0.0211 (3)
O9A0.01476 (17)0.33786 (10)0.67684 (6)0.0193 (2)
O10A0.1254 (2)0.42475 (12)0.75432 (7)0.0286 (3)
O11A0.07426 (19)0.03387 (11)0.40540 (6)0.0219 (3)
H11A0.13570.01360.42190.033*
C1A0.0605 (2)0.30858 (13)0.56292 (8)0.0136 (3)
H1A0.12850.37460.56740.016*
C2A0.0309 (2)0.26188 (13)0.62915 (8)0.0154 (3)
H2A0.06060.20580.62700.018*
C3A0.2144 (2)0.21871 (13)0.64991 (8)0.0141 (3)
C4A0.2974 (2)0.18345 (13)0.58571 (8)0.0129 (3)
C5A0.1790 (2)0.22646 (12)0.53140 (7)0.0116 (3)
C6A0.0753 (2)0.13291 (13)0.50537 (8)0.0147 (3)
H6A0.05590.13900.51240.018*
C7A0.1199 (2)0.12857 (13)0.43446 (8)0.0153 (3)
H7A0.04910.18370.41230.018*
C8A0.3188 (2)0.16099 (13)0.43317 (7)0.0134 (3)
H8A0.38700.10580.45630.016*
C9A0.3177 (2)0.25622 (12)0.47859 (7)0.0116 (3)
C10A0.2891 (2)0.36256 (13)0.44944 (8)0.0139 (3)
H10A0.36280.36790.41020.017*
C11A0.3674 (2)0.43433 (14)0.49988 (8)0.0151 (3)
C12A0.4887 (2)0.27250 (13)0.51990 (7)0.0131 (3)
H12A0.59780.25360.49570.016*
C13A0.2857 (2)0.06556 (13)0.57760 (8)0.0155 (3)
C14A0.2983 (2)0.31438 (13)0.68223 (8)0.0166 (3)
H14A0.34540.36000.64790.020*
C15A0.1343 (3)0.36608 (14)0.70958 (9)0.0204 (3)
C16A0.4481 (3)0.29640 (16)0.73098 (9)0.0252 (4)
H16A0.48750.36270.74870.038*
H16B0.54840.26250.71020.038*
H16C0.40470.25240.76550.038*
C17A0.4033 (2)0.17030 (14)0.36585 (8)0.0171 (3)
C18A0.2843 (3)0.23041 (17)0.31799 (8)0.0226 (4)
H18A0.33950.23000.27590.034*
H18B0.27120.30170.33270.034*
H18C0.16650.19770.31500.034*
C19A0.4275 (3)0.06132 (16)0.33818 (9)0.0270 (4)
H19A0.31010.03050.32960.040*
H19B0.49390.01860.36900.040*
H19C0.49380.06560.29830.040*
C20A0.5922 (2)0.21718 (16)0.37150 (8)0.0206 (3)
H20A0.66410.17700.40210.031*
H20B0.58390.28860.38640.031*
H20C0.64870.21570.32960.031*
O1B0.37642 (16)0.23496 (10)0.00320 (6)0.0178 (2)
H1HB0.39200.27760.02640.027*
O2B0.61554 (18)0.04031 (11)0.16805 (6)0.0207 (3)
H2HB0.70720.01210.18370.031*
O3B0.94462 (16)0.10996 (10)0.06296 (6)0.0166 (2)
O4B0.62239 (17)0.04148 (9)0.00060 (6)0.0170 (2)
O5B0.64412 (17)0.31774 (10)0.08190 (6)0.0180 (2)
H5HB0.65620.36660.10780.027*
O6B0.84724 (19)0.43445 (11)0.01391 (7)0.0235 (3)
O7B0.97973 (16)0.28380 (10)0.03741 (6)0.0182 (2)
O8B0.80101 (19)0.09892 (11)0.07933 (6)0.0225 (3)
O9B0.45961 (19)0.25553 (11)0.15083 (6)0.0220 (3)
O10B0.6126 (2)0.33470 (12)0.22943 (7)0.0292 (3)
O11B0.57728 (19)0.02014 (11)0.13452 (6)0.0222 (3)
H11B0.62260.07470.12000.033*
C1B0.5365 (2)0.22233 (13)0.03826 (8)0.0133 (3)
H1B0.59870.29010.04330.016*
C2B0.4957 (2)0.17680 (13)0.10383 (8)0.0165 (3)
H2B0.39390.12710.10050.020*
C3B0.6665 (2)0.12164 (13)0.12719 (8)0.0159 (3)
C4B0.7584 (2)0.08721 (13)0.06466 (8)0.0139 (3)
C5B0.6639 (2)0.14185 (12)0.00859 (7)0.0118 (3)
C6B0.5623 (2)0.05577 (12)0.02715 (8)0.0141 (3)
H6B0.43000.06440.02480.017*
C7B0.6286 (2)0.06384 (13)0.09516 (8)0.0146 (3)
H7B0.57300.12700.11430.018*
C8B0.8299 (2)0.08659 (13)0.08607 (7)0.0130 (3)
H8B0.88170.02560.06320.016*
C9B0.82132 (19)0.17495 (13)0.03565 (7)0.0119 (3)
C10B0.8125 (2)0.28688 (13)0.05862 (8)0.0143 (3)
H10B0.90110.29630.09330.017*
C11B0.8768 (2)0.34667 (14)0.00000 (8)0.0171 (3)
C12B0.9781 (2)0.17819 (13)0.01261 (8)0.0151 (3)
H12B1.09320.16130.00840.018*
C13B0.7335 (2)0.02818 (14)0.05136 (8)0.0162 (3)
C14B0.7643 (2)0.20958 (14)0.16239 (8)0.0187 (3)
H14B0.82690.25140.12950.022*
C15B0.6111 (3)0.27390 (15)0.18651 (8)0.0215 (3)
C16B0.9015 (3)0.18147 (17)0.21383 (9)0.0277 (4)
H16D0.93860.24390.23690.042*
H16E1.00550.14990.19400.042*
H16F0.84870.13260.24380.042*
C17B0.9404 (2)0.09985 (14)0.14806 (8)0.0162 (3)
C18B0.8508 (2)0.17222 (15)0.19726 (8)0.0196 (3)
H18D0.84510.24210.17960.029*
H18E0.72980.14760.20710.029*
H18F0.92060.17300.23640.029*
C19B0.9631 (3)0.00728 (15)0.17895 (9)0.0232 (4)
H19D0.84700.03190.19500.035*
H19E1.01050.05580.14700.035*
H19F1.04610.00220.21450.035*
C20B1.1300 (2)0.13842 (16)0.13184 (9)0.0205 (3)
H20D1.20220.13710.17040.031*
H20E1.18460.09360.09930.031*
H20F1.12400.20910.11550.031*
O1W0.5019 (2)0.53009 (13)0.26802 (8)0.0334 (3)
O2W0.2407 (13)0.0403 (4)0.1721 (4)0.0346 (16)0.72 (3)
O2W'0.181 (3)0.0269 (7)0.1514 (11)0.032 (3)0.28 (3)
O3W0.2362 (6)0.5574 (3)0.36358 (18)0.0241 (11)0.494 (10)
O3W'0.1490 (7)0.5294 (3)0.34387 (18)0.0307 (14)0.506 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0114 (5)0.0213 (6)0.0219 (6)0.0031 (4)0.0002 (4)0.0012 (5)
O2A0.0233 (6)0.0159 (6)0.0158 (5)0.0005 (5)0.0049 (5)0.0039 (5)
O3A0.0113 (5)0.0201 (6)0.0133 (5)0.0004 (4)0.0003 (4)0.0039 (4)
O4A0.0214 (6)0.0121 (5)0.0186 (5)0.0019 (4)0.0004 (5)0.0007 (4)
O5A0.0142 (5)0.0172 (6)0.0219 (6)0.0033 (4)0.0042 (4)0.0038 (5)
O6A0.0229 (6)0.0132 (6)0.0252 (6)0.0018 (5)0.0001 (5)0.0016 (5)
O7A0.0156 (5)0.0152 (6)0.0182 (5)0.0021 (4)0.0034 (4)0.0006 (4)
O8A0.0283 (7)0.0165 (6)0.0185 (6)0.0067 (5)0.0021 (5)0.0021 (5)
O9A0.0240 (6)0.0169 (6)0.0171 (6)0.0029 (5)0.0070 (5)0.0025 (5)
O10A0.0425 (8)0.0221 (7)0.0213 (6)0.0017 (6)0.0048 (6)0.0078 (5)
O11A0.0278 (7)0.0159 (6)0.0220 (6)0.0058 (5)0.0020 (5)0.0050 (5)
C1A0.0111 (6)0.0134 (7)0.0164 (7)0.0004 (5)0.0008 (5)0.0011 (6)
C2A0.0161 (7)0.0127 (7)0.0175 (7)0.0004 (6)0.0056 (6)0.0019 (6)
C3A0.0178 (7)0.0117 (6)0.0130 (7)0.0004 (5)0.0034 (5)0.0001 (5)
C4A0.0129 (6)0.0129 (7)0.0130 (7)0.0002 (5)0.0015 (5)0.0005 (5)
C5A0.0105 (6)0.0121 (6)0.0122 (6)0.0000 (5)0.0008 (5)0.0003 (5)
C6A0.0145 (7)0.0111 (6)0.0185 (7)0.0012 (5)0.0007 (5)0.0006 (6)
C7A0.0170 (7)0.0136 (7)0.0152 (7)0.0022 (6)0.0004 (6)0.0028 (6)
C8A0.0148 (7)0.0130 (7)0.0126 (7)0.0004 (5)0.0014 (5)0.0003 (5)
C9A0.0108 (6)0.0129 (6)0.0111 (6)0.0006 (5)0.0000 (5)0.0001 (5)
C10A0.0131 (7)0.0133 (7)0.0154 (7)0.0004 (5)0.0005 (5)0.0011 (6)
C11A0.0146 (7)0.0152 (7)0.0155 (7)0.0015 (6)0.0012 (6)0.0013 (6)
C12A0.0115 (6)0.0147 (7)0.0132 (6)0.0004 (5)0.0002 (5)0.0008 (6)
C13A0.0186 (7)0.0140 (7)0.0140 (7)0.0008 (6)0.0053 (6)0.0005 (6)
C14A0.0210 (7)0.0144 (7)0.0144 (7)0.0025 (6)0.0011 (6)0.0010 (6)
C15A0.0298 (9)0.0144 (7)0.0170 (7)0.0001 (6)0.0039 (6)0.0003 (6)
C16A0.0286 (9)0.0267 (9)0.0201 (8)0.0026 (7)0.0060 (7)0.0021 (7)
C17A0.0197 (7)0.0182 (8)0.0136 (7)0.0015 (6)0.0023 (6)0.0008 (6)
C18A0.0241 (8)0.0298 (9)0.0137 (7)0.0017 (7)0.0020 (6)0.0009 (7)
C19A0.0405 (11)0.0212 (9)0.0196 (8)0.0026 (8)0.0096 (8)0.0040 (7)
C20A0.0180 (7)0.0280 (9)0.0159 (7)0.0024 (7)0.0049 (6)0.0030 (7)
O1B0.0120 (5)0.0169 (6)0.0243 (6)0.0014 (4)0.0005 (4)0.0046 (5)
O2B0.0267 (6)0.0183 (6)0.0173 (5)0.0028 (5)0.0045 (5)0.0066 (5)
O3B0.0114 (5)0.0216 (6)0.0169 (5)0.0020 (4)0.0013 (4)0.0017 (5)
O4B0.0192 (6)0.0120 (5)0.0198 (6)0.0018 (4)0.0004 (5)0.0013 (4)
O5B0.0166 (5)0.0156 (6)0.0218 (6)0.0004 (5)0.0008 (4)0.0038 (5)
O6B0.0246 (6)0.0163 (6)0.0298 (7)0.0043 (5)0.0037 (5)0.0054 (5)
O7B0.0164 (5)0.0199 (6)0.0183 (5)0.0045 (5)0.0014 (4)0.0033 (5)
O8B0.0293 (7)0.0165 (6)0.0218 (6)0.0071 (5)0.0010 (5)0.0052 (5)
O9B0.0280 (7)0.0205 (6)0.0176 (6)0.0070 (5)0.0067 (5)0.0007 (5)
O10B0.0503 (9)0.0204 (7)0.0170 (6)0.0047 (6)0.0058 (6)0.0024 (5)
O11B0.0271 (7)0.0181 (6)0.0214 (6)0.0053 (5)0.0026 (5)0.0067 (5)
C1B0.0105 (6)0.0133 (7)0.0161 (7)0.0006 (5)0.0022 (5)0.0018 (6)
C2B0.0177 (7)0.0144 (7)0.0177 (7)0.0026 (6)0.0061 (6)0.0011 (6)
C3B0.0199 (7)0.0141 (7)0.0137 (7)0.0016 (6)0.0028 (6)0.0028 (6)
C4B0.0140 (7)0.0144 (7)0.0132 (7)0.0010 (5)0.0001 (5)0.0009 (5)
C5B0.0104 (6)0.0117 (6)0.0133 (6)0.0007 (5)0.0006 (5)0.0018 (5)
C6B0.0128 (6)0.0116 (7)0.0179 (7)0.0011 (5)0.0007 (5)0.0002 (6)
C7B0.0149 (7)0.0141 (7)0.0147 (7)0.0023 (5)0.0018 (5)0.0020 (6)
C8B0.0132 (7)0.0126 (7)0.0132 (6)0.0002 (5)0.0003 (5)0.0001 (5)
C9B0.0080 (6)0.0143 (7)0.0136 (6)0.0012 (5)0.0019 (5)0.0003 (5)
C10B0.0138 (7)0.0131 (7)0.0160 (7)0.0012 (5)0.0022 (5)0.0001 (6)
C11B0.0141 (7)0.0182 (7)0.0192 (7)0.0061 (6)0.0036 (6)0.0014 (6)
C12B0.0122 (7)0.0168 (7)0.0161 (7)0.0007 (6)0.0001 (5)0.0011 (6)
C13B0.0168 (7)0.0158 (7)0.0162 (7)0.0025 (6)0.0042 (6)0.0002 (6)
C14B0.0247 (8)0.0181 (8)0.0134 (7)0.0003 (6)0.0006 (6)0.0010 (6)
C15B0.0321 (9)0.0173 (8)0.0152 (7)0.0027 (7)0.0045 (7)0.0029 (6)
C16B0.0341 (10)0.0276 (10)0.0212 (9)0.0033 (8)0.0090 (8)0.0028 (8)
C17B0.0159 (7)0.0183 (7)0.0145 (7)0.0012 (6)0.0028 (5)0.0003 (6)
C18B0.0227 (8)0.0220 (8)0.0141 (7)0.0016 (7)0.0015 (6)0.0010 (6)
C19B0.0284 (9)0.0202 (8)0.0212 (8)0.0040 (7)0.0059 (7)0.0037 (7)
C20B0.0157 (7)0.0259 (9)0.0199 (8)0.0001 (6)0.0039 (6)0.0006 (7)
O1W0.0482 (9)0.0226 (7)0.0288 (7)0.0042 (7)0.0135 (7)0.0040 (6)
O2W0.036 (3)0.0330 (14)0.035 (2)0.0011 (15)0.001 (2)0.0102 (15)
O2W'0.035 (6)0.024 (3)0.037 (6)0.006 (3)0.007 (5)0.011 (3)
O3W0.024 (2)0.0230 (15)0.0255 (16)0.0037 (13)0.0003 (14)0.0079 (12)
O3W'0.036 (3)0.0327 (18)0.0235 (17)0.0104 (18)0.0065 (17)0.0123 (14)
Geometric parameters (Å, º) top
O1A—C1A1.411 (2)O1B—H1HB0.8400
O1A—H1HA0.8400O2B—C3B1.415 (2)
O2A—C3A1.413 (2)O2B—H2HB0.8400
O2A—H2HA0.8400O3B—C12B1.402 (2)
O3A—C12A1.402 (2)O3B—C4B1.427 (2)
O3A—C4A1.426 (2)O4B—C13B1.350 (2)
O4A—C13A1.342 (2)O4B—C6B1.457 (2)
O4A—C6A1.466 (2)O5B—C10B1.403 (2)
O5A—C10A1.402 (2)O5B—H5HB0.8400
O5A—H5HA0.8400O6B—C11B1.197 (2)
O6A—C11A1.202 (2)O7B—C11B1.361 (2)
O7A—C11A1.360 (2)O7B—C12B1.465 (2)
O7A—C12A1.462 (2)O8B—C13B1.196 (2)
O8A—C13A1.197 (2)O9B—C15B1.369 (2)
O9A—C15A1.351 (2)O9B—C2B1.447 (2)
O9A—C2A1.448 (2)O10B—C15B1.196 (2)
O10A—C15A1.210 (2)O11B—C7B1.415 (2)
O11A—C7A1.410 (2)O11B—H11B0.8400
O11A—H11A0.8400C1B—C2B1.530 (2)
C1A—C2A1.533 (2)C1B—C5B1.552 (2)
C1A—C5A1.543 (2)C1B—H1B1.0000
C1A—H1A1.0000C2B—C3B1.539 (2)
C2A—C3A1.540 (2)C2B—H2B1.0000
C2A—H2A1.0000C3B—C14B1.537 (2)
C3A—C14A1.542 (2)C3B—C4B1.555 (2)
C3A—C4A1.559 (2)C4B—C13B1.533 (2)
C4A—C5A1.535 (2)C4B—C5B1.534 (2)
C4A—C13A1.541 (2)C5B—C6B1.538 (2)
C5A—C6A1.536 (2)C5B—C9B1.572 (2)
C5A—C9A1.578 (2)C6B—C7B1.520 (2)
C6A—C7A1.528 (2)C6B—H6B1.0000
C6A—H6A1.0000C7B—C8B1.546 (2)
C7A—C8A1.550 (2)C7B—H7B1.0000
C7A—H7A1.0000C8B—C9B1.560 (2)
C8A—C9A1.559 (2)C8B—C17B1.561 (2)
C8A—C17A1.560 (2)C8B—H8B1.0000
C8A—H8A1.0000C9B—C10B1.531 (2)
C9A—C10A1.522 (2)C9B—C12B1.537 (2)
C9A—C12A1.548 (2)C10B—C11B1.523 (2)
C10A—C11A1.518 (2)C10B—H10B1.0000
C10A—H10A1.0000C12B—H12B1.0000
C12A—H12A1.0000C14B—C15B1.513 (3)
C14A—C15A1.521 (3)C14B—C16B1.520 (3)
C14A—C16A1.522 (2)C14B—H14B1.0000
C14A—H14A1.0000C16B—H16D0.9800
C16A—H16A0.9800C16B—H16E0.9800
C16A—H16B0.9800C16B—H16F0.9800
C16A—H16C0.9800C17B—C20B1.539 (2)
C17A—C19A1.540 (3)C17B—C18B1.539 (2)
C17A—C18A1.542 (2)C17B—C19B1.543 (3)
C17A—C20A1.544 (2)C18B—H18D0.9800
C18A—H18A0.9800C18B—H18E0.9800
C18A—H18B0.9800C18B—H18F0.9800
C18A—H18C0.9800C19B—H19D0.9800
C19A—H19A0.9800C19B—H19E0.9800
C19A—H19B0.9800C19B—H19F0.9800
C19A—H19C0.9800C20B—H20D0.9800
C20A—H20A0.9800C20B—H20E0.9800
C20A—H20B0.9800C20B—H20F0.9800
C20A—H20C0.9800O2W—O2W'0.641 (17)
O1B—C1B1.405 (2)O3W—O3W'0.849 (4)
C1A—O1A—H1HA109.5C1B—O1B—H1HB109.5
C3A—O2A—H2HA109.5C3B—O2B—H2HB109.5
C12A—O3A—C4A109.87 (12)C12B—O3B—C4B109.70 (12)
C13A—O4A—C6A112.43 (13)C13B—O4B—C6B112.67 (13)
C10A—O5A—H5HA109.5C10B—O5B—H5HB109.5
C11A—O7A—C12A110.74 (13)C11B—O7B—C12B110.82 (13)
C15A—O9A—C2A109.33 (13)C15B—O9B—C2B109.33 (14)
C7A—O11A—H11A109.5C7B—O11B—H11B109.5
O1A—C1A—C2A110.46 (13)O1B—C1B—C2B109.35 (13)
O1A—C1A—C5A115.33 (13)O1B—C1B—C5B113.27 (13)
C2A—C1A—C5A101.98 (13)C2B—C1B—C5B103.50 (13)
O1A—C1A—H1A109.6O1B—C1B—H1B110.2
C2A—C1A—H1A109.6C2B—C1B—H1B110.2
C5A—C1A—H1A109.6C5B—C1B—H1B110.2
O9A—C2A—C1A113.22 (14)O9B—C2B—C1B112.34 (14)
O9A—C2A—C3A105.87 (13)O9B—C2B—C3B106.04 (14)
C1A—C2A—C3A104.84 (13)C1B—C2B—C3B106.63 (13)
O9A—C2A—H2A110.9O9B—C2B—H2B110.6
C1A—C2A—H2A110.9C1B—C2B—H2B110.6
C3A—C2A—H2A110.9C3B—C2B—H2B110.6
O2A—C3A—C2A108.85 (13)O2B—C3B—C14B113.27 (13)
O2A—C3A—C14A112.22 (13)O2B—C3B—C2B107.87 (13)
C2A—C3A—C14A100.75 (13)C14B—C3B—C2B101.21 (14)
O2A—C3A—C4A113.48 (13)O2B—C3B—C4B115.01 (14)
C2A—C3A—C4A103.36 (13)C14B—C3B—C4B113.70 (14)
C14A—C3A—C4A116.64 (13)C2B—C3B—C4B104.15 (13)
O3A—C4A—C5A109.25 (12)O3B—C4B—C13B108.28 (13)
O3A—C4A—C13A108.94 (13)O3B—C4B—C5B108.92 (13)
C5A—C4A—C13A104.36 (13)C13B—C4B—C5B105.00 (13)
O3A—C4A—C3A115.08 (13)O3B—C4B—C3B114.15 (13)
C5A—C4A—C3A107.33 (13)C13B—C4B—C3B112.25 (13)
C13A—C4A—C3A111.31 (13)C5B—C4B—C3B107.81 (13)
C4A—C5A—C6A104.95 (13)C4B—C5B—C6B104.77 (13)
C4A—C5A—C1A105.29 (13)C4B—C5B—C1B106.49 (13)
C6A—C5A—C1A113.94 (13)C6B—C5B—C1B112.36 (13)
C4A—C5A—C9A103.23 (12)C4B—C5B—C9B103.63 (12)
C6A—C5A—C9A106.26 (12)C6B—C5B—C9B106.37 (12)
C1A—C5A—C9A121.45 (13)C1B—C5B—C9B121.68 (13)
O4A—C6A—C7A108.19 (13)O4B—C6B—C7B109.24 (13)
O4A—C6A—C5A106.67 (13)O4B—C6B—C5B106.73 (12)
C7A—C6A—C5A104.83 (13)C7B—C6B—C5B103.81 (12)
O4A—C6A—H6A112.2O4B—C6B—H6B112.2
C7A—C6A—H6A112.2C7B—C6B—H6B112.2
C5A—C6A—H6A112.2C5B—C6B—H6B112.2
O11A—C7A—C6A113.31 (14)O11B—C7B—C6B113.75 (14)
O11A—C7A—C8A117.05 (14)O11B—C7B—C8B118.25 (14)
C6A—C7A—C8A103.51 (13)C6B—C7B—C8B103.41 (12)
O11A—C7A—H7A107.5O11B—C7B—H7B106.9
C6A—C7A—H7A107.5C6B—C7B—H7B106.9
C8A—C7A—H7A107.5C8B—C7B—H7B106.9
C7A—C8A—C9A100.88 (12)C7B—C8B—C9B99.89 (12)
C7A—C8A—C17A116.27 (13)C7B—C8B—C17B116.72 (13)
C9A—C8A—C17A119.77 (13)C9B—C8B—C17B120.67 (13)
C7A—C8A—H8A106.3C7B—C8B—H8B106.1
C9A—C8A—H8A106.3C9B—C8B—H8B106.1
C17A—C8A—H8A106.3C17B—C8B—H8B106.1
C10A—C9A—C12A102.09 (12)C10B—C9B—C12B102.06 (13)
C10A—C9A—C8A118.41 (12)C10B—C9B—C8B119.11 (13)
C12A—C9A—C8A115.82 (13)C12B—C9B—C8B115.13 (13)
C10A—C9A—C5A114.39 (13)C10B—C9B—C5B114.54 (13)
C12A—C9A—C5A101.00 (12)C12B—C9B—C5B101.14 (12)
C8A—C9A—C5A104.13 (12)C8B—C9B—C5B103.77 (12)
O5A—C10A—C11A113.93 (14)O5B—C10B—C11B113.89 (14)
O5A—C10A—C9A114.13 (13)O5B—C10B—C9B114.43 (13)
C11A—C10A—C9A103.12 (13)C11B—C10B—C9B102.63 (13)
O5A—C10A—H10A108.5O5B—C10B—H10B108.5
C11A—C10A—H10A108.5C11B—C10B—H10B108.5
C9A—C10A—H10A108.5C9B—C10B—H10B108.5
O6A—C11A—O7A122.30 (16)O6B—C11B—O7B122.39 (17)
O6A—C11A—C10A128.32 (16)O6B—C11B—C10B128.53 (17)
O7A—C11A—C10A109.38 (14)O7B—C11B—C10B109.08 (15)
O3A—C12A—O7A108.35 (13)O3B—C12B—O7B108.93 (13)
O3A—C12A—C9A109.72 (12)O3B—C12B—C9B109.39 (13)
O7A—C12A—C9A105.19 (13)O7B—C12B—C9B105.07 (13)
O3A—C12A—H12A111.1O3B—C12B—H12B111.1
O7A—C12A—H12A111.1O7B—C12B—H12B111.1
C9A—C12A—H12A111.1C9B—C12B—H12B111.1
O8A—C13A—O4A122.38 (16)O8B—C13B—O4B122.50 (17)
O8A—C13A—C4A127.71 (16)O8B—C13B—C4B127.64 (16)
O4A—C13A—C4A109.89 (14)O4B—C13B—C4B109.84 (14)
C15A—C14A—C16A114.00 (15)C15B—C14B—C16B113.80 (15)
C15A—C14A—C3A101.17 (14)C15B—C14B—C3B102.16 (15)
C16A—C14A—C3A117.47 (15)C16B—C14B—C3B118.20 (16)
C15A—C14A—H14A107.9C15B—C14B—H14B107.4
C16A—C14A—H14A107.9C16B—C14B—H14B107.4
C3A—C14A—H14A107.9C3B—C14B—H14B107.4
O10A—C15A—O9A120.49 (18)O10B—C15B—O9B121.46 (18)
O10A—C15A—C14A128.64 (19)O10B—C15B—C14B128.11 (19)
O9A—C15A—C14A110.87 (14)O9B—C15B—C14B110.42 (15)
C14A—C16A—H16A109.5C14B—C16B—H16D109.5
C14A—C16A—H16B109.5C14B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C14A—C16A—H16C109.5C14B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
C19A—C17A—C18A106.88 (15)C20B—C17B—C18B109.87 (15)
C19A—C17A—C20A106.08 (15)C20B—C17B—C19B106.12 (15)
C18A—C17A—C20A111.73 (15)C18B—C17B—C19B108.58 (14)
C19A—C17A—C8A108.73 (14)C20B—C17B—C8B110.70 (13)
C18A—C17A—C8A112.76 (14)C18B—C17B—C8B113.07 (14)
C20A—C17A—C8A110.34 (13)C19B—C17B—C8B108.23 (14)
C17A—C18A—H18A109.5C17B—C18B—H18D109.5
C17A—C18A—H18B109.5C17B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C17A—C19A—H19A109.5C17B—C19B—H19D109.5
C17A—C19A—H19B109.5C17B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C17A—C19A—H19C109.5C17B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C17A—C20A—H20A109.5C17B—C20B—H20D109.5
C17A—C20A—H20B109.5C17B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
C17A—C20A—H20C109.5C17B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
C15A—O9A—C2A—C1A95.94 (16)C15B—O9B—C2B—C1B97.88 (16)
C15A—O9A—C2A—C3A18.37 (17)C15B—O9B—C2B—C3B18.23 (17)
O1A—C1A—C2A—O9A79.85 (17)O1B—C1B—C2B—O9B88.63 (17)
C5A—C1A—C2A—O9A157.05 (13)C5B—C1B—C2B—O9B150.38 (13)
O1A—C1A—C2A—C3A165.21 (13)O1B—C1B—C2B—C3B155.62 (13)
C5A—C1A—C2A—C3A42.12 (15)C5B—C1B—C2B—C3B34.63 (17)
O9A—C2A—C3A—O2A86.17 (15)O9B—C2B—C3B—O2B88.43 (15)
C1A—C2A—C3A—O2A153.87 (13)C1B—C2B—C3B—O2B151.66 (13)
O9A—C2A—C3A—C14A31.97 (15)O9B—C2B—C3B—C14B30.72 (16)
C1A—C2A—C3A—C14A87.99 (14)C1B—C2B—C3B—C14B89.19 (15)
O9A—C2A—C3A—C4A152.92 (13)O9B—C2B—C3B—C4B148.92 (13)
C1A—C2A—C3A—C4A32.96 (16)C1B—C2B—C3B—C4B29.01 (17)
C12A—O3A—C4A—C5A1.92 (17)C12B—O3B—C4B—C13B116.35 (14)
C12A—O3A—C4A—C13A111.51 (15)C12B—O3B—C4B—C5B2.69 (18)
C12A—O3A—C4A—C3A122.70 (15)C12B—O3B—C4B—C3B117.84 (15)
O2A—C3A—C4A—O3A109.38 (16)O2B—C3B—C4B—O3B109.10 (16)
C2A—C3A—C4A—O3A132.90 (14)C14B—C3B—C4B—O3B23.8 (2)
C14A—C3A—C4A—O3A23.4 (2)C2B—C3B—C4B—O3B133.07 (14)
O2A—C3A—C4A—C5A128.79 (14)O2B—C3B—C4B—C13B14.6 (2)
C2A—C3A—C4A—C5A11.07 (16)C14B—C3B—C4B—C13B147.53 (14)
C14A—C3A—C4A—C5A98.42 (16)C2B—C3B—C4B—C13B103.23 (15)
O2A—C3A—C4A—C13A15.17 (19)O2B—C3B—C4B—C5B129.76 (14)
C2A—C3A—C4A—C13A102.55 (15)C14B—C3B—C4B—C5B97.32 (16)
C14A—C3A—C4A—C13A147.96 (15)C2B—C3B—C4B—C5B11.93 (17)
O3A—C4A—C5A—C6A128.63 (13)O3B—C4B—C5B—C6B125.49 (13)
C13A—C4A—C5A—C6A12.25 (16)C13B—C4B—C5B—C6B9.70 (16)
C3A—C4A—C5A—C6A105.97 (14)C3B—C4B—C5B—C6B110.15 (14)
O3A—C4A—C5A—C1A110.81 (14)O3B—C4B—C5B—C1B115.28 (14)
C13A—C4A—C5A—C1A132.81 (13)C13B—C4B—C5B—C1B128.93 (13)
C3A—C4A—C5A—C1A14.59 (16)C3B—C4B—C5B—C1B9.08 (17)
O3A—C4A—C5A—C9A17.50 (16)O3B—C4B—C5B—C9B14.16 (16)
C13A—C4A—C5A—C9A98.89 (14)C13B—C4B—C5B—C9B101.63 (14)
C3A—C4A—C5A—C9A142.90 (13)C3B—C4B—C5B—C9B138.52 (13)
O1A—C1A—C5A—C4A154.23 (13)O1B—C1B—C5B—C4B144.86 (13)
C2A—C1A—C5A—C4A34.51 (15)C2B—C1B—C5B—C4B26.55 (16)
O1A—C1A—C5A—C6A39.77 (19)O1B—C1B—C5B—C6B30.71 (18)
C2A—C1A—C5A—C6A79.96 (16)C2B—C1B—C5B—C6B87.60 (15)
O1A—C1A—C5A—C9A89.32 (17)O1B—C1B—C5B—C9B97.02 (17)
C2A—C1A—C5A—C9A150.95 (13)C2B—C1B—C5B—C9B144.68 (14)
C13A—O4A—C6A—C7A112.63 (15)C13B—O4B—C6B—C7B116.95 (14)
C13A—O4A—C6A—C5A0.33 (17)C13B—O4B—C6B—C5B5.30 (17)
C4A—C5A—C6A—O4A8.27 (16)C4B—C5B—C6B—O4B9.29 (16)
C1A—C5A—C6A—O4A122.93 (14)C1B—C5B—C6B—O4B124.49 (14)
C9A—C5A—C6A—O4A100.68 (13)C9B—C5B—C6B—O4B100.06 (14)
C4A—C5A—C6A—C7A122.87 (13)C4B—C5B—C6B—C7B124.64 (13)
C1A—C5A—C6A—C7A122.47 (14)C1B—C5B—C6B—C7B120.16 (14)
C9A—C5A—C6A—C7A13.92 (16)C9B—C5B—C6B—C7B15.29 (16)
O4A—C6A—C7A—O11A51.43 (18)O4B—C6B—C7B—O11B55.60 (17)
C5A—C6A—C7A—O11A164.96 (14)C5B—C6B—C7B—O11B169.16 (13)
O4A—C6A—C7A—C8A76.37 (15)O4B—C6B—C7B—C8B73.92 (15)
C5A—C6A—C7A—C8A37.16 (16)C5B—C6B—C7B—C8B39.63 (15)
O11A—C7A—C8A—C9A170.92 (14)O11B—C7B—C8B—C9B174.74 (14)
C6A—C7A—C8A—C9A45.49 (15)C6B—C7B—C8B—C9B48.01 (15)
O11A—C7A—C8A—C17A57.9 (2)O11B—C7B—C8B—C17B53.4 (2)
C6A—C7A—C8A—C17A176.69 (14)C6B—C7B—C8B—C17B179.89 (13)
C7A—C8A—C9A—C10A92.30 (15)C7B—C8B—C9B—C10B91.47 (15)
C17A—C8A—C9A—C10A36.7 (2)C17B—C8B—C9B—C10B37.9 (2)
C7A—C8A—C9A—C12A145.94 (13)C7B—C8B—C9B—C12B146.83 (13)
C17A—C8A—C9A—C12A85.07 (17)C17B—C8B—C9B—C12B83.82 (18)
C7A—C8A—C9A—C5A36.04 (14)C7B—C8B—C9B—C5B37.28 (14)
C17A—C8A—C9A—C5A165.03 (14)C17B—C8B—C9B—C5B166.63 (13)
C4A—C5A—C9A—C10A133.24 (13)C4B—C5B—C9B—C10B132.54 (14)
C6A—C5A—C9A—C10A116.60 (14)C6B—C5B—C9B—C10B117.31 (14)
C1A—C5A—C9A—C10A15.8 (2)C1B—C5B—C9B—C10B13.0 (2)
C4A—C5A—C9A—C12A24.43 (15)C4B—C5B—C9B—C12B23.63 (15)
C6A—C5A—C9A—C12A134.59 (13)C6B—C5B—C9B—C12B133.78 (13)
C1A—C5A—C9A—C12A93.04 (16)C1B—C5B—C9B—C12B95.89 (16)
C4A—C5A—C9A—C8A96.00 (13)C4B—C5B—C9B—C8B95.97 (14)
C6A—C5A—C9A—C8A14.16 (15)C6B—C5B—C9B—C8B14.18 (15)
C1A—C5A—C9A—C8A146.53 (14)C1B—C5B—C9B—C8B144.51 (14)
C12A—C9A—C10A—O5A153.96 (13)C12B—C9B—C10B—O5B154.98 (13)
C8A—C9A—C10A—O5A77.56 (18)C8B—C9B—C10B—O5B76.99 (17)
C5A—C9A—C10A—O5A45.82 (18)C5B—C9B—C10B—O5B46.64 (18)
C12A—C9A—C10A—C11A29.85 (15)C12B—C9B—C10B—C11B31.09 (15)
C8A—C9A—C10A—C11A158.33 (13)C8B—C9B—C10B—C11B159.13 (13)
C5A—C9A—C10A—C11A78.29 (15)C5B—C9B—C10B—C11B77.25 (16)
C12A—O7A—C11A—O6A174.33 (16)C12B—O7B—C11B—O6B173.99 (15)
C12A—O7A—C11A—C10A6.51 (17)C12B—O7B—C11B—C10B6.06 (17)
O5A—C10A—C11A—O6A32.9 (2)O5B—C10B—C11B—O6B31.7 (2)
C9A—C10A—C11A—O6A157.15 (17)C9B—C10B—C11B—O6B155.94 (17)
O5A—C10A—C11A—O7A148.00 (14)O5B—C10B—C11B—O7B148.36 (13)
C9A—C10A—C11A—O7A23.76 (16)C9B—C10B—C11B—O7B24.11 (16)
C4A—O3A—C12A—O7A99.00 (14)C4B—O3B—C12B—O7B94.98 (14)
C4A—O3A—C12A—C9A15.34 (17)C4B—O3B—C12B—C9B19.36 (17)
C11A—O7A—C12A—O3A130.56 (13)C11B—O7B—C12B—O3B131.72 (13)
C11A—O7A—C12A—C9A13.28 (16)C11B—O7B—C12B—C9B14.61 (16)
C10A—C9A—C12A—O3A143.27 (13)C10B—C9B—C12B—O3B145.27 (13)
C8A—C9A—C12A—O3A86.62 (16)C8B—C9B—C12B—O3B84.21 (16)
C5A—C9A—C12A—O3A25.12 (16)C5B—C9B—C12B—O3B26.92 (16)
C10A—C9A—C12A—O7A26.92 (15)C10B—C9B—C12B—O7B28.47 (15)
C8A—C9A—C12A—O7A157.03 (13)C8B—C9B—C12B—O7B158.99 (12)
C5A—C9A—C12A—O7A91.23 (13)C5B—C9B—C12B—O7B89.88 (13)
C6A—O4A—C13A—O8A170.71 (15)C6B—O4B—C13B—O8B177.69 (16)
C6A—O4A—C13A—C4A7.94 (18)C6B—O4B—C13B—C4B1.15 (18)
O3A—C4A—C13A—O8A49.2 (2)O3B—C4B—C13B—O8B55.5 (2)
C5A—C4A—C13A—O8A165.76 (16)C5B—C4B—C13B—O8B171.69 (17)
C3A—C4A—C13A—O8A78.8 (2)C3B—C4B—C13B—O8B71.5 (2)
O3A—C4A—C13A—O4A129.40 (13)O3B—C4B—C13B—O4B123.30 (14)
C5A—C4A—C13A—O4A12.80 (17)C5B—C4B—C13B—O4B7.07 (18)
C3A—C4A—C13A—O4A102.66 (15)C3B—C4B—C13B—O4B109.78 (15)
O2A—C3A—C14A—C15A83.24 (16)O2B—C3B—C14B—C15B84.36 (17)
C2A—C3A—C14A—C15A32.40 (15)C2B—C3B—C14B—C15B30.85 (15)
C4A—C3A—C14A—C15A143.40 (14)C4B—C3B—C14B—C15B141.89 (14)
O2A—C3A—C14A—C16A41.5 (2)O2B—C3B—C14B—C16B41.4 (2)
C2A—C3A—C14A—C16A157.14 (15)C2B—C3B—C14B—C16B156.58 (16)
C4A—C3A—C14A—C16A91.86 (18)C4B—C3B—C14B—C16B92.38 (19)
C2A—O9A—C15A—O10A175.77 (17)C2B—O9B—C15B—O10B178.39 (17)
C2A—O9A—C15A—C14A3.89 (19)C2B—O9B—C15B—C14B2.70 (19)
C16A—C14A—C15A—O10A28.5 (3)C16B—C14B—C15B—O10B30.4 (3)
C3A—C14A—C15A—O10A155.55 (19)C3B—C14B—C15B—O10B158.99 (19)
C16A—C14A—C15A—O9A151.13 (16)C16B—C14B—C15B—O9B150.75 (16)
C3A—C14A—C15A—O9A24.07 (18)C3B—C14B—C15B—O9B22.19 (18)
C7A—C8A—C17A—C19A71.80 (19)C7B—C8B—C17B—C20B171.23 (14)
C9A—C8A—C17A—C19A166.55 (15)C9B—C8B—C17B—C20B49.8 (2)
C7A—C8A—C17A—C18A46.5 (2)C7B—C8B—C17B—C18B47.5 (2)
C9A—C8A—C17A—C18A75.11 (19)C9B—C8B—C17B—C18B74.01 (19)
C7A—C8A—C17A—C20A172.26 (14)C7B—C8B—C17B—C19B72.86 (18)
C9A—C8A—C17A—C20A50.6 (2)C9B—C8B—C17B—C19B165.67 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1HA···O5A0.842.042.749 (2)142
O1A—H1HA···O4Ai0.842.583.141 (2)126
O2A—H2HA···O1Wii0.841.992.809 (2)164
O5A—H5HA···O3W0.842.092.839 (3)148
O5A—H5HA···O3W0.841.842.664 (3)169
O11A—H11A···O1Aiii0.842.292.991 (2)141
O1B—H1HB···O5B0.842.302.911 (2)131
O1B—H1HB···O8Biv0.842.413.052 (2)133
O1B—H1HB···O4Biv0.842.412.901 (2)118
O2B—H2HB···O10Aii0.842.122.924 (2)161
O5B—H5HB···O2Wiv0.841.982.786 (3)162
O5B—H5HB···O2Wiv0.842.072.821 (8)149
O11B—H11B···O9Bv0.842.372.943 (2)126
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x, y1/2, z+1; (iv) x+1, y+1/2, z; (v) x+1, y1/2, z.
(IV) (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS) 3-(1,1-dimethylethyl) hexahydro-2,4,7 b-trihydroxy-8-methyl-9H-1,7a-(epoxymethano)-1H, 6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d] furan-5,9,12(4H)-trione dihydrate top
Crystal data top
C20H24O10·2H2ODx = 1.518 Mg m3
Mr = 460.42Melting point: 563 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 11.403 (2) ÅCell parameters from 14293 reflections
b = 12.950 (3) Åθ = 2.8–27.9°
c = 13.646 (3) ŵ = 0.13 mm1
V = 2015.0 (6) Å3T = 120 K
Z = 4Fragment, colorless
F(000) = 9760.25 × 0.22 × 0.17 mm
Data collection top
KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
2586 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 27.9°, θmin = 2.8°
ω scans with κ offsetsh = 1415
14293 measured reflectionsk = 1617
2694 independent reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0386P)2 + 0.6511P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2694 reflectionsΔρmax = 0.26 e Å3
309 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (3)
Crystal data top
C20H24O10·2H2OV = 2015.0 (6) Å3
Mr = 460.42Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.403 (2) ŵ = 0.13 mm1
b = 12.950 (3) ÅT = 120 K
c = 13.646 (3) Å0.25 × 0.22 × 0.17 mm
Data collection top
KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
2586 reflections with I > 2σ(I)
14293 measured reflectionsRint = 0.019
2694 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.26 e Å3
2694 reflectionsΔρmin = 0.17 e Å3
309 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 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
O20.89516 (11)0.43124 (9)0.08845 (9)0.0162 (3)
H2O0.90310.48940.06200.024*
O30.63959 (10)0.55267 (9)0.18044 (9)0.0145 (2)
O40.63682 (11)0.36463 (9)0.00180 (8)0.0181 (3)
O50.44990 (12)0.27533 (9)0.31404 (9)0.0190 (3)
H5O0.40120.25690.35680.029*
O60.53218 (12)0.42106 (10)0.46168 (9)0.0203 (3)
O70.55683 (11)0.53109 (9)0.33608 (8)0.0172 (3)
O80.70092 (12)0.52541 (10)0.02604 (9)0.0194 (3)
O90.90598 (11)0.33764 (10)0.29614 (9)0.0191 (3)
O101.02699 (12)0.45612 (12)0.35842 (10)0.0252 (3)
O110.41869 (13)0.27086 (10)0.01610 (9)0.0225 (3)
H11O0.42340.20650.02280.034*
C10.69230 (15)0.31630 (13)0.25775 (12)0.0160 (3)
H1A0.68090.34940.32250.019*
H1B0.67380.24180.26310.019*
C20.81734 (15)0.33285 (13)0.22017 (12)0.0160 (3)
H20.83790.27800.17160.019*
C30.81882 (14)0.43986 (13)0.17012 (11)0.0137 (3)
C40.68881 (14)0.45976 (12)0.14137 (11)0.0131 (3)
C50.61617 (15)0.36872 (12)0.17859 (12)0.0136 (3)
C60.59242 (15)0.30448 (13)0.08526 (12)0.0161 (3)
H60.62900.23440.08890.019*
C70.45905 (16)0.29877 (13)0.07781 (12)0.0168 (3)
H70.42970.24710.12640.020*
C80.41981 (15)0.40776 (13)0.11068 (13)0.0151 (3)
H80.45230.45730.06150.018*
C90.49548 (14)0.42006 (12)0.20512 (12)0.0136 (3)
C100.44483 (15)0.38219 (12)0.30251 (12)0.0153 (3)
H100.36100.40440.30670.018*
C110.51543 (15)0.44340 (13)0.37697 (12)0.0163 (3)
C120.53437 (15)0.53106 (12)0.22918 (12)0.0144 (3)
H120.47210.58210.21140.017*
C130.67654 (14)0.45726 (13)0.03025 (12)0.0154 (3)
C140.86641 (15)0.51005 (13)0.25073 (12)0.0161 (3)
H140.79890.52800.29430.019*
C150.94412 (15)0.43648 (14)0.30749 (12)0.0186 (3)
C160.92400 (16)0.61125 (14)0.22032 (14)0.0209 (4)
H16A0.95710.64530.27820.031*
H16B0.86530.65640.19010.031*
H16C0.98670.59710.17310.031*
C170.28463 (15)0.42727 (13)0.11447 (13)0.0191 (4)
C180.21603 (16)0.33658 (15)0.15828 (15)0.0246 (4)
H18A0.24230.32440.22570.037*
H18B0.22980.27450.11890.037*
H18C0.13210.35290.15830.037*
C190.24266 (16)0.44408 (15)0.00800 (14)0.0247 (4)
H19A0.15690.44910.00690.037*
H19B0.26770.38570.03270.037*
H19C0.27670.50810.01770.037*
C200.25540 (16)0.52809 (14)0.16890 (15)0.0245 (4)
H20A0.30200.58470.14150.037*
H20B0.27380.52010.23860.037*
H20C0.17180.54360.16120.037*
O1W0.81086 (15)0.26008 (11)0.53321 (12)0.0322 (3)
H1W0.731 (3)0.233 (2)0.521 (2)0.048*
H2W0.812 (3)0.324 (2)0.514 (2)0.048*
O2W0.58843 (14)0.18812 (13)0.49780 (13)0.0344 (4)
H3W0.553 (3)0.152 (2)0.552 (2)0.052*
H4W0.541 (3)0.234 (3)0.490 (2)0.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0187 (6)0.0163 (5)0.0135 (6)0.0022 (5)0.0050 (5)0.0002 (5)
O30.0141 (5)0.0117 (5)0.0177 (6)0.0004 (4)0.0023 (5)0.0006 (4)
O40.0233 (6)0.0178 (6)0.0133 (5)0.0006 (5)0.0017 (5)0.0021 (5)
O50.0237 (6)0.0144 (5)0.0190 (6)0.0039 (5)0.0039 (5)0.0012 (5)
O60.0238 (6)0.0225 (6)0.0147 (6)0.0024 (5)0.0003 (5)0.0019 (5)
O70.0217 (6)0.0160 (5)0.0139 (5)0.0045 (5)0.0005 (5)0.0032 (4)
O80.0225 (6)0.0210 (6)0.0145 (5)0.0008 (5)0.0002 (5)0.0027 (5)
O90.0178 (6)0.0217 (6)0.0179 (6)0.0024 (5)0.0030 (5)0.0040 (5)
O100.0196 (6)0.0337 (7)0.0222 (6)0.0009 (6)0.0063 (5)0.0010 (6)
O110.0319 (7)0.0174 (6)0.0183 (6)0.0011 (5)0.0077 (6)0.0057 (5)
C10.0181 (8)0.0147 (7)0.0153 (7)0.0015 (6)0.0005 (6)0.0020 (6)
C20.0174 (7)0.0158 (7)0.0147 (7)0.0024 (6)0.0016 (7)0.0020 (6)
C30.0159 (7)0.0147 (7)0.0104 (7)0.0013 (6)0.0017 (6)0.0009 (6)
C40.0163 (7)0.0119 (7)0.0110 (7)0.0015 (6)0.0007 (6)0.0007 (6)
C50.0159 (7)0.0120 (7)0.0128 (7)0.0013 (6)0.0004 (6)0.0004 (6)
C60.0205 (8)0.0135 (7)0.0143 (7)0.0009 (6)0.0001 (7)0.0015 (6)
C70.0207 (8)0.0148 (7)0.0149 (7)0.0010 (6)0.0030 (7)0.0015 (6)
C80.0166 (7)0.0142 (7)0.0146 (7)0.0005 (6)0.0028 (6)0.0006 (6)
C90.0148 (7)0.0121 (7)0.0138 (7)0.0002 (6)0.0005 (6)0.0010 (6)
C100.0174 (7)0.0143 (7)0.0143 (7)0.0009 (6)0.0008 (7)0.0009 (6)
C110.0159 (7)0.0170 (7)0.0159 (8)0.0002 (6)0.0028 (6)0.0031 (6)
C120.0150 (7)0.0150 (7)0.0131 (7)0.0005 (6)0.0003 (6)0.0016 (6)
C130.0140 (7)0.0191 (8)0.0131 (7)0.0026 (6)0.0007 (6)0.0026 (6)
C140.0147 (7)0.0208 (8)0.0129 (7)0.0014 (6)0.0008 (6)0.0020 (6)
C150.0166 (8)0.0257 (8)0.0135 (7)0.0031 (7)0.0019 (6)0.0003 (7)
C160.0211 (8)0.0186 (8)0.0230 (9)0.0026 (7)0.0013 (7)0.0028 (7)
C170.0158 (7)0.0186 (8)0.0228 (9)0.0002 (7)0.0023 (7)0.0023 (7)
C180.0183 (8)0.0264 (9)0.0292 (9)0.0066 (7)0.0005 (8)0.0013 (8)
C190.0207 (8)0.0266 (9)0.0266 (9)0.0000 (8)0.0087 (8)0.0005 (8)
C200.0174 (8)0.0240 (9)0.0322 (10)0.0032 (7)0.0021 (8)0.0055 (8)
O1W0.0398 (8)0.0215 (7)0.0353 (8)0.0014 (6)0.0159 (7)0.0042 (6)
O2W0.0295 (7)0.0339 (8)0.0399 (9)0.0050 (7)0.0022 (7)0.0138 (7)
Geometric parameters (Å, º) top
O2—C31.419 (2)C7—H71.0000
O2—H2O0.8400C8—C91.559 (2)
O3—C121.400 (2)C8—C171.563 (2)
O3—C41.431 (2)C8—H81.0000
O4—C131.340 (2)C9—C101.530 (2)
O4—C61.470 (2)C9—C121.540 (2)
O5—C101.394 (2)C10—C111.519 (2)
O5—H5O0.8400C10—H101.0000
O6—C111.207 (2)C12—H121.0000
O7—C111.350 (2)C14—C151.514 (2)
O7—C121.481 (2)C14—C161.523 (2)
O8—C131.203 (2)C14—H141.0000
O9—C151.361 (2)C16—H16A0.9800
O9—C21.449 (2)C16—H16B0.9800
O10—C151.200 (2)C16—H16C0.9800
O11—C71.409 (2)C17—C181.533 (3)
O11—H11O0.8400C17—C201.539 (2)
C1—C21.530 (2)C17—C191.545 (2)
C1—C51.543 (2)C18—H18A0.9800
C1—H1A0.9900C18—H18B0.9800
C1—H1B0.9900C18—H18C0.9800
C2—C31.545 (2)C19—H19A0.9800
C2—H21.0000C19—H19B0.9800
C3—C141.527 (2)C19—H19C0.9800
C3—C41.555 (2)C20—H20A0.9800
C4—C131.523 (2)C20—H20B0.9800
C4—C51.528 (2)C20—H20C0.9800
C5—C61.545 (2)O1W—H1W0.98 (3)
C5—C91.571 (2)O1W—H2W0.87 (3)
C6—C71.526 (2)O2W—H3W0.96 (3)
C6—H61.0000O2W—H4W0.81 (3)
C7—C81.547 (2)
C3—O2—H2O109.5C8—C9—C5104.54 (13)
C12—O3—C4110.19 (12)O5—C10—C11114.86 (14)
C13—O4—C6111.49 (12)O5—C10—C9113.61 (13)
C10—O5—H5O109.5C11—C10—C9102.34 (13)
C11—O7—C12110.26 (12)O5—C10—H10108.6
C15—O9—C2110.16 (13)C11—C10—H10108.6
C7—O11—H11O109.5C9—C10—H10108.6
C2—C1—C5103.18 (13)O6—C11—O7122.82 (16)
C2—C1—H1A111.1O6—C11—C10126.82 (16)
C5—C1—H1A111.1O7—C11—C10110.34 (14)
C2—C1—H1B111.1O3—C12—O7108.64 (13)
C5—C1—H1B111.1O3—C12—C9109.40 (13)
H1A—C1—H1B109.1O7—C12—C9105.07 (13)
O9—C2—C1114.59 (13)O3—C12—H12111.2
O9—C2—C3105.68 (13)O7—C12—H12111.2
C1—C2—C3106.49 (13)C9—C12—H12111.2
O9—C2—H2110.0O8—C13—O4123.38 (15)
C1—C2—H2110.0O8—C13—C4126.80 (16)
C3—C2—H2110.0O4—C13—C4109.79 (14)
O2—C3—C14113.25 (13)C15—C14—C16115.36 (15)
O2—C3—C2106.47 (13)C15—C14—C3101.65 (13)
C14—C3—C2102.67 (13)C16—C14—C3117.97 (14)
O2—C3—C4113.57 (13)C15—C14—H14107.1
C14—C3—C4114.96 (13)C16—C14—H14107.1
C2—C3—C4104.46 (13)C3—C14—H14107.1
O3—C4—C13110.66 (13)O10—C15—O9121.12 (17)
O3—C4—C5108.20 (12)O10—C15—C14128.58 (17)
C13—C4—C5105.35 (13)O9—C15—C14110.28 (14)
O3—C4—C3114.79 (13)C14—C16—H16A109.5
C13—C4—C3109.58 (13)C14—C16—H16B109.5
C5—C4—C3107.77 (13)H16A—C16—H16B109.5
C4—C5—C1105.50 (13)C14—C16—H16C109.5
C4—C5—C6103.68 (13)H16A—C16—H16C109.5
C1—C5—C6116.02 (13)H16B—C16—H16C109.5
C4—C5—C9103.01 (12)C18—C17—C20110.57 (15)
C1—C5—C9121.18 (13)C18—C17—C19108.47 (15)
C6—C5—C9105.33 (13)C20—C17—C19105.50 (15)
O4—C6—C7108.50 (14)C18—C17—C8113.10 (15)
O4—C6—C5107.04 (13)C20—C17—C8111.52 (14)
C7—C6—C5104.81 (13)C19—C17—C8107.29 (15)
O4—C6—H6112.0C17—C18—H18A109.5
C7—C6—H6112.0C17—C18—H18B109.5
C5—C6—H6112.0H18A—C18—H18B109.5
O11—C7—C6113.49 (15)C17—C18—H18C109.5
O11—C7—C8113.79 (14)H18A—C18—H18C109.5
C6—C7—C8102.98 (14)H18B—C18—H18C109.5
O11—C7—H7108.8C17—C19—H19A109.5
C6—C7—H7108.8C17—C19—H19B109.5
C8—C7—H7108.8H19A—C19—H19B109.5
C7—C8—C999.95 (13)C17—C19—H19C109.5
C7—C8—C17116.25 (14)H19A—C19—H19C109.5
C9—C8—C17120.14 (15)H19B—C19—H19C109.5
C7—C8—H8106.5C17—C20—H20A109.5
C9—C8—H8106.5C17—C20—H20B109.5
C17—C8—H8106.5H20A—C20—H20B109.5
C10—C9—C12102.87 (13)C17—C20—H20C109.5
C10—C9—C8118.45 (14)H20A—C20—H20C109.5
C12—C9—C8115.53 (13)H20B—C20—H20C109.5
C10—C9—C5113.30 (13)H1W—O1W—H2W107 (3)
C12—C9—C5101.07 (12)H3W—O2W—H4W100 (3)
C15—O9—C2—C1106.89 (16)C1—C5—C9—C1019.3 (2)
C15—O9—C2—C310.03 (17)C6—C5—C9—C10114.89 (14)
C5—C1—C2—O9151.68 (13)C4—C5—C9—C1227.40 (15)
C5—C1—C2—C335.23 (16)C1—C5—C9—C1290.01 (17)
O9—C2—C3—O293.77 (14)C6—C5—C9—C12135.77 (13)
C1—C2—C3—O2143.96 (13)C4—C5—C9—C892.89 (14)
O9—C2—C3—C1425.46 (16)C1—C5—C9—C8149.70 (14)
C1—C2—C3—C1496.81 (15)C6—C5—C9—C815.47 (16)
O9—C2—C3—C4145.77 (13)C12—C9—C10—O5153.82 (14)
C1—C2—C3—C423.50 (16)C8—C9—C10—O577.38 (19)
C12—O3—C4—C13107.78 (15)C5—C9—C10—O545.59 (19)
C12—O3—C4—C57.17 (16)C12—C9—C10—C1129.39 (15)
C12—O3—C4—C3127.55 (13)C8—C9—C10—C11158.19 (14)
O2—C3—C4—O3121.28 (14)C5—C9—C10—C1178.83 (16)
C14—C3—C4—O311.42 (19)C12—O7—C11—O6173.33 (16)
C2—C3—C4—O3123.13 (14)C12—O7—C11—C108.16 (18)
O2—C3—C4—C133.96 (19)O5—C10—C11—O633.7 (2)
C14—C3—C4—C13136.66 (15)C9—C10—C11—O6157.25 (17)
C2—C3—C4—C13111.63 (14)O5—C10—C11—O7147.91 (15)
O2—C3—C4—C5118.10 (14)C9—C10—C11—O724.32 (17)
C14—C3—C4—C5109.20 (15)C4—O3—C12—O7102.28 (14)
C2—C3—C4—C52.51 (16)C4—O3—C12—C911.91 (17)
O3—C4—C5—C1105.61 (14)C11—O7—C12—O3128.49 (14)
C13—C4—C5—C1136.00 (13)C11—O7—C12—C911.50 (17)
C3—C4—C5—C119.07 (16)C10—C9—C12—O3142.18 (13)
O3—C4—C5—C6131.98 (13)C8—C9—C12—O387.23 (16)
C13—C4—C5—C613.59 (16)C5—C9—C12—O324.92 (16)
C3—C4—C5—C6103.35 (14)C10—C9—C12—O725.70 (16)
O3—C4—C5—C922.38 (15)C8—C9—C12—O7156.29 (13)
C13—C4—C5—C996.02 (14)C5—C9—C12—O791.56 (14)
C3—C4—C5—C9147.05 (13)C6—O4—C13—O8168.71 (16)
C2—C1—C5—C433.15 (16)C6—O4—C13—C413.12 (18)
C2—C1—C5—C680.96 (17)O3—C4—C13—O848.2 (2)
C2—C1—C5—C9149.31 (14)C5—C4—C13—O8164.88 (17)
C13—O4—C6—C7108.74 (15)C3—C4—C13—O879.4 (2)
C13—O4—C6—C53.88 (18)O3—C4—C13—O4133.75 (14)
C4—C5—C6—O46.70 (16)C5—C4—C13—O417.02 (18)
C1—C5—C6—O4121.84 (15)C3—C4—C13—O498.67 (15)
C9—C5—C6—O4101.17 (14)O2—C3—C14—C1584.48 (16)
C4—C5—C6—C7121.81 (14)C2—C3—C14—C1529.90 (16)
C1—C5—C6—C7123.05 (15)C4—C3—C14—C15142.67 (14)
C9—C5—C6—C713.94 (17)O2—C3—C14—C1642.7 (2)
O4—C6—C7—O1147.91 (18)C2—C3—C14—C16157.11 (14)
C5—C6—C7—O11162.00 (13)C4—C3—C14—C1690.12 (17)
O4—C6—C7—C875.55 (15)C2—O9—C15—O10171.24 (16)
C5—C6—C7—C838.53 (16)C2—O9—C15—C1410.22 (18)
O11—C7—C8—C9170.61 (14)C16—C14—C15—O1026.7 (3)
C6—C7—C8—C947.34 (15)C3—C14—C15—O10155.60 (18)
O11—C7—C8—C1758.5 (2)C16—C14—C15—O9154.89 (15)
C6—C7—C8—C17178.25 (15)C3—C14—C15—O926.00 (17)
C7—C8—C9—C1089.10 (16)C7—C8—C17—C1842.1 (2)
C17—C8—C9—C1039.3 (2)C9—C8—C17—C1878.49 (19)
C7—C8—C9—C12148.25 (14)C7—C8—C17—C20167.48 (15)
C17—C8—C9—C1283.35 (19)C9—C8—C17—C2046.9 (2)
C7—C8—C9—C538.15 (15)C7—C8—C17—C1977.46 (18)
C17—C8—C9—C5166.54 (14)C9—C8—C17—C19161.94 (14)
C4—C5—C9—C10136.75 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O6i0.841.942.709 (2)152
O5—H5O···O1Wii0.841.832.659 (2)167
O11—H11O···O2iii0.842.022.810 (2)156
O1W—H1W···O2W0.98 (3)1.76 (3)2.745 (2)178 (3)
O1W—H2W···O8iv0.87 (3)2.03 (3)2.896 (2)175 (3)
O2W—H3W···O10ii0.96 (3)1.89 (3)2.798 (2)158 (3)
O2W—H3W···O9ii0.96 (3)2.67 (3)3.514 (2)147 (2)
O2W—H4W···O60.81 (3)2.46 (3)3.123 (2)140 (3)
O2W—H4W···O1Wii0.81 (3)2.64 (3)3.263 (2)135 (3)
O2W—H4W···O50.81 (3)2.67 (3)3.172 (2)122 (3)
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x1/2, y+1/2, z+1; (iii) x1/2, y+1/2, z; (iv) x+3/2, y+1, z+1/2.

Experimental details

(I)(III)(IV)
Crystal data
Chemical formulaC20H24O9·H2OC20H24O11·1.5H2OC20H24O10·2H2O
Mr426.41467.42460.42
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21Orthorhombic, P212121
Temperature (K)120120120
a, b, c (Å)8.931 (2), 12.338 (2), 17.779 (3)7.4945 (15), 12.973 (3), 20.934 (4)11.403 (2), 12.950 (3), 13.646 (3)
α, β, γ (°)90, 90, 9090, 91.00 (2), 9090, 90, 90
V3)1959.2 (6)2035.0 (7)2015.0 (6)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.120.130.13
Crystal size (mm)0.48 × 0.37 × 0.350.47 × 0.27 × 0.250.25 × 0.22 × 0.17
Data collection
DiffractometerKappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
KappaCCD (with Oxford Cryosystems Cryostream cooler)
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19931, 4144, 3936 22429, 5921, 5752 14293, 2694, 2586
Rint0.0170.0190.019
(sin θ/λ)max1)0.7700.6950.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.083, 1.06 0.031, 0.086, 1.05 0.029, 0.074, 1.03
No. of reflections414459212694
No. of parameters283622309
No. of restraints010
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.210.37, 0.180.26, 0.17

Computer programs: COLLECT (Nonius 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O1Wi0.841.892.694 (2)160
O5—H5O···O1Wii0.841.932.764 (2)172
O1W—H1W···O80.86 (2)1.98 (2)2.831 (2)175 (2)
O1W—H2W···O10iii0.83 (2)1.90 (2)2.711 (2)169 (2)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y1/2, z+1/2; (iii) x+1/2, y+1, z1/2.
Endocyclic torsion angles (°) in ginkgolides A, C, and J hydrates top
AtomsGinkgolide AGinkgolide CGinkgolide CGinkgolide J
Molecule AMolecule B
Ring A
C1-C2-C3-C427.84 (12)-32.96 (16)-29.01 (17)-23.50 (16)
C2-C3-C4-C5-24.67 (12)11.07 (16)11.93 (17)2.51 (16)
C3-C4-C5-C112.57 (12)14.59 (16)9.08 (17)19.07 (16)
C4-C5-C1-C24.88 (12)-34.51 (15)-26.55 (16)-33.15 (16)
C5-C1-C2-C3-20.79 (12)42.12 (15)34.63 (17)35.23 (16)
Ring B
C9-C5-C6-C7-13.21 (12)-13.92 (16)-15.29 (16)-13.94 (17)
C5-C6-C7-C835.47 (12)37.16 (16)39.63 (15)38.53 (16)
C6-C7-C8-C9-43.50 (12)-45.49 (15)-48.01 (15)-47.34 (15)
C7-C8-C9-C534.67 (11)36.04 (14)37.28 (14)38.15 (15)
C8-C9-C5-C6-13.49 (11)-14.16 (15)-14.18 (15)-15.47 (16)
Ring C
C12-C9-C10-C11-32.36 (11)-29.85 (15)-31.09 (15)-29.39 (15)
C9-C10-C11-O729.50 (12)23.76 (16)24.11 (16)24.32 (17)
C10-C11-O7-C12-13.07 (13)-6.51 (17)-6.06 (17)-8.16 (18)
C11-O7-C12-C9-8.61 (12)-13.28 (16)-14.61 (16)-11.50 (17)
O7-C12-C9-C1025.99 (11)26.92 (15)28.47 (15)25.70 (16)
Ring D
O3-C4-C5-C916.88 (11)17.50 (16)14.16 (16)22.38 (15)
C4-C5-C9-C12-23.49 (10)-24.43 (15)-23.63 (15)-27.40 (15)
C5-C9-C12-O323.62 (11)25.12 (16)26.92 (16)24.92 (16)
C9-C12-O3-C4-14.06 (12)-15.34 (17)-19.36 (17)-11.91 (17)
C5-C4-O3-C12-2.29 (12)-1.92 (17)2.69 (18)-7.17 (16)
Ring E
C13-C4-C5-C610.27 (11)12.25 (16)9.70 (16)13.59 (16)
C4-C5-C6-O4-6.06 (12)-8.27 (16)-9.29 (16)-6.70 (16)
C5-C6-O4-C13-1.17 (13)0.33 (17)5.30 (17)-3.88 (18)
C6-O4-C13-C48.17 (13)7.94 (18)1.15 (18)13.12 (18)
O4-C13-C4-C5-11.80 (13)-12.80 (17)-7.07 (18)-17.02 (18)
Ring F
O9-C2-C3-C1429.98 (11)-31.97 (15)-30.72 (16)-25.46 (16)
C2-C3-C14-C15-24.93 (11)32.40 (15)30.85 (15)29.90 (16)
C3-C14-C15-O911.65 (13)-24.07 (18)-22.19 (18)-26.00 (17)
C14-C15-O9-C27.87 (13)3.89 (19)2.70 (19)10.22 (18)
C15-O9-C2-C3-23.99 (12)18.37 (17)18.23 (17)10.03 (17)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O1A—H1HA···O5A0.842.042.749 (2)142.2
O1A—H1HA···O4Ai0.842.583.141 (2)125.7
O2A—H2HA···O1Wii0.841.992.809 (2)164.1
O5A—H5HA···O3W0.842.092.839 (3)147.7
O5A—H5HA···O3W'0.841.842.664 (3)168.6
O11A—H11A···O1Aiii0.842.292.991 (2)140.7
O1B—H1HB···O5B0.842.302.911 (2)130.5
O1B—H1HB···O8Biv0.842.413.052 (2)133.3
O1B—H1HB···O4Biv0.842.412.901 (2)118.0
O2B—H2HB···O10Aii0.842.122.924 (2)160.7
O5B—H5HB···O2Wiv0.841.982.786 (3)161.5
O5B—H5HB···O2W'iv0.842.072.821 (8)149.4
O11B—H11B···O9Bv0.842.372.943 (2)125.6
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x, y1/2, z+1; (iv) x+1, y+1/2, z; (v) x+1, y1/2, z.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O6i0.841.942.709 (2)152
O5—H5O···O1Wii0.841.832.659 (2)167
O11—H11O···O2iii0.842.022.810 (2)156
O1W—H1W···O2W0.98 (3)1.76 (3)2.745 (2)178 (3)
O1W—H2W···O8iv0.87 (3)2.03 (3)2.896 (2)175 (3)
O2W—H3W···O10ii0.96 (3)1.89 (3)2.798 (2)158 (3)
O2W—H3W···O9ii0.96 (3)2.67 (3)3.514 (2)147 (2)
O2W—H4W···O60.81 (3)2.46 (3)3.123 (2)140 (3)
O2W—H4W···O1Wii0.81 (3)2.64 (3)3.263 (2)135 (3)
O2W—H4W···O50.81 (3)2.67 (3)3.172 (2)122 (3)
Symmetry codes: (i) x+3/2, y+1, z1/2; (ii) x1/2, y+1/2, z+1; (iii) x1/2, y+1/2, z; (iv) x+3/2, y+1, z+1/2.
 

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