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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3210.
Published online 2010 November 17. doi:  10.1107/S1600536810046362
PMCID: PMC3011509

(3R,6R,12R,20S,24S)-20,24-Ep­oxy­dammarane-3,6,12,25-tetraol dihydrate

Abstract

The title compound, C30H52O5·2H2O, was degraded from pseudoginsenoside F11 which was extracted and seperated from Panax quinquefolium saponin. The three six-membered rings are in chair conformations. The five-membered ring is in an envelope conformation and the tetra­hydro­furan ring has a conformation inter­mediate between half-chair and envelope. In the crystal, inter­molecular O—H(...)O hydrogen bonds link mol­ecules into a three-dimensional network. Intra­molecular O—H(...)O hydrogen bonds also occur.

Related literature

For background and the medicinal properties of Panax ginseng and Panax quinquefolium, see: Iljin et al. (1982 [triangle]); Shi et al. (1992 [triangle]); Shibata et al. (1985 [triangle]); Takano et al. (1999 [triangle]); Yu et al. (2007 [triangle]).

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Object name is e-66-o3210-scheme1.jpg

Experimental

Crystal data

  • C30H52O5·2H2O
  • M r = 528.75
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3210-efi1.jpg
  • a = 11.4575 (15) Å
  • b = 15.457 (2) Å
  • c = 16.726 (2) Å
  • V = 2962.2 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.51 × 0.38 × 0.32 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 15595 measured reflections
  • 3095 independent reflections
  • 2768 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.108
  • S = 1.05
  • 3095 reflections
  • 346 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046362/lh5154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046362/lh5154Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors would like to thank the Shandong Provincial Natural Science Foundation, China (Y2007C138), the Scientific Reasearch Foundation of the Higher Education Institutions of Shandong Province, China (J07WE26) and the National Natural Science Foundation of China (No.81001358) for research grants.

supplementary crystallographic information

Comment

Both Panax ginseng and Panax quinquefolium, belonging to Araliaceae, are well known traditional medicinal herbs. They are used as tonics and for the treatment for diseases, such as tumor and myocardial ischemia. Panax ginseng contains a number of saponins, namely ginsenoside and an oleanolic acid-type saponin in addition to the major protopanaxadiol and protopanaxatriol-type saponins (Shibata et al.,1985). Panax quinquefolium contains an ocotillol-type (20S, 24R-epoxyside) saponin with high anti-tumor activity (Takano et al.,1999), as well as oleanolic acid-type saponin, protopanaxadiol and protopanaxatriol-type saponins. (3R,6R,12R,20S,24S)-20,24-epoxy-dammarane-3,6,12,25-tetraol is found to possess cardioprotective effects on myocardial injury induced by isoproterenol in rats (Yu et al.,2007). As part of our ongoing investigation of ocotillol-type compounds and their cardioprotective effect on myocardial injury, we report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. In the molecule, all bond lengths and angles are within normal ranges (Shi et al.,1992; Iljin et al.,1982). The six-membered rings A(C3/C4/C5/C6/C7/C8), B(C7/C8/C10/C11/C12/C14), and C(C12/C14/C15/C16/C17/C18) are in chair conformations that depart significantly from ideal geometry to accommodate for intramolecular non-bonded 1,3-diaxial interactions involving the methyl groups. The five-membered ring D(C13/C14/C15/C16/C17) has an envelope form with C18 as the out-of-plane atom. The tetrahydrofuran ring has a conformation intermediate between half-chair and envelope forms. In the crystal structure intermolecular O-H···O hydrogen bonds link molecules into a three-dimensional network.

Experimental

Pseudoginsenoside F11 was extracted and seperated from Panax quinquefolium saponin. (3R,6R,12R,20S,24S)-20,24-epoxy-dammarane-3,6,12,25-tetraol was degraded from Pseudoginsenoside F11 with sodium in glycerine and seperated by flash chromatography. Finally, the crystals were dried at room temperature. Single crystals of compound (I) suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

Refinement

H atoms bonded to C atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances in the range 0.96–0.98 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). The H atoms bonded to hydroxy O atoms were included with O-H = 0.82Å and Uiso(H) = 1.5Ueq(O) and water H atoms were included in 'as-found' positions with Uiso(H) = 0.12Å3. In the absence of anomlaous dispersion effects Friedel pairs were merged. The absolute configuration is based on unchanging stereochemical centers in the synthesis.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are not shown.

Crystal data

C30H52O5·2H2OF(000) = 1168
Mr = 528.75Dx = 1.186 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5972 reflections
a = 11.4575 (15) Åθ = 2.4–28.0°
b = 15.457 (2) ŵ = 0.08 mm1
c = 16.726 (2) ÅT = 298 K
V = 2962.2 (7) Å3Block, colourless
Z = 40.51 × 0.38 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer2768 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
graphiteθmax = 25.5°, θmin = 2.2°
[var phi] and ω scansh = −13→13
15595 measured reflectionsk = −18→18
3095 independent reflectionsl = −10→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0592P)2 + 0.5608P] where P = (Fo2 + 2Fc2)/3
3095 reflections(Δ/σ)max < 0.001
346 parametersΔρmax = 0.18 e Å3
6 restraintsΔρmin = −0.16 e Å3

Special details

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)

xyzUiso*/Ueq
C10.7657 (3)0.50304 (19)0.18423 (19)0.0600 (8)
H1A0.78410.55410.15410.090*
H1B0.83260.48590.21490.090*
H1C0.70170.51490.21960.090*
C20.6080 (2)0.44716 (19)0.09599 (19)0.0546 (7)
H2A0.60270.50580.07740.082*
H2B0.55310.43840.13860.082*
H2C0.59040.40830.05280.082*
C30.7318 (2)0.42959 (16)0.12652 (17)0.0436 (6)
C40.8223 (2)0.43365 (17)0.05835 (17)0.0453 (6)
H4A0.89990.43270.08310.054*
C50.8168 (3)0.35892 (18)0.00041 (16)0.0485 (7)
H5A0.87690.3658−0.04000.058*
H5B0.74170.3588−0.02620.058*
C60.8343 (3)0.27323 (17)0.04358 (15)0.0437 (6)
H6A0.91260.27160.06540.052*
H6B0.82760.22650.00510.052*
C70.7463 (2)0.25757 (16)0.11176 (14)0.0367 (5)
C80.7455 (2)0.33919 (15)0.16833 (15)0.0370 (5)
H80.82370.34050.19200.044*
C90.6270 (2)0.23805 (18)0.07120 (16)0.0452 (6)
H9A0.62000.27180.02320.068*
H9B0.56480.25270.10720.068*
H9C0.62270.17770.05810.068*
C100.6633 (2)0.32106 (15)0.23917 (16)0.0402 (6)
H100.58640.30640.21730.048*
C110.7058 (2)0.24394 (16)0.28745 (15)0.0431 (6)
H11A0.65100.23390.33070.052*
H11B0.78020.25890.31140.052*
C120.7209 (2)0.15891 (15)0.24068 (14)0.0363 (5)
C130.5974 (2)0.12287 (18)0.22259 (17)0.0451 (6)
H13A0.56190.10350.27140.068*
H13B0.60360.07520.18600.068*
H13C0.55040.16760.19920.068*
C140.7921 (2)0.17999 (15)0.16346 (15)0.0359 (5)
H140.86780.20000.18360.043*
C150.8217 (2)0.09726 (16)0.11639 (15)0.0416 (6)
H15A0.75000.07130.09700.050*
H15B0.86900.11240.07040.050*
C160.8869 (2)0.03177 (16)0.16698 (15)0.0397 (6)
H160.95970.05830.18560.048*
C170.8132 (2)0.00865 (15)0.23932 (14)0.0367 (5)
H170.7367−0.00910.21900.044*
C180.7928 (2)0.09115 (16)0.29063 (15)0.0404 (6)
C190.9103 (3)0.12856 (18)0.32081 (17)0.0514 (7)
H19A0.89690.16240.36810.077*
H19B0.94390.16450.28010.077*
H19C0.96280.08200.33300.077*
C200.7324 (3)0.05094 (18)0.36378 (15)0.0518 (7)
H20A0.73300.09050.40880.062*
H20B0.65230.03530.35160.062*
C210.8061 (3)−0.02966 (19)0.38146 (16)0.0542 (7)
H21A0.7589−0.07390.40680.065*
H21B0.8705−0.01530.41670.065*
C220.8527 (2)−0.06215 (16)0.29903 (15)0.0414 (6)
H220.9382−0.06290.30080.050*
C230.8091 (2)−0.15422 (16)0.28113 (15)0.0406 (6)
C240.8690 (3)−0.2194 (2)0.33484 (18)0.0605 (8)
H24A0.8404−0.27630.32300.091*
H24B0.8529−0.20570.38970.091*
H24C0.9517−0.21740.32580.091*
C250.6758 (2)−0.16592 (19)0.28239 (19)0.0530 (7)
H25A0.6509−0.19160.33250.064*
H25B0.6368−0.11060.27590.064*
C260.6484 (3)−0.2245 (3)0.2139 (2)0.0717 (10)
H26A0.5886−0.19910.18030.086*
H26B0.6202−0.27980.23340.086*
C270.7600 (2)−0.23660 (17)0.16702 (16)0.0441 (6)
H270.7902−0.29480.17770.053*
C280.7516 (3)−0.22421 (18)0.07639 (16)0.0462 (6)
C290.6604 (3)−0.2842 (2)0.0421 (2)0.0706 (9)
H29A0.5848−0.26810.06190.106*
H29B0.6775−0.34260.05770.106*
H29C0.6609−0.2800−0.01520.106*
C300.8687 (3)−0.2400 (2)0.03777 (18)0.0629 (9)
H30A0.8627−0.2304−0.01880.094*
H30B0.8925−0.29860.04750.094*
H30C0.9253−0.20110.06000.094*
O10.71201 (17)−0.13798 (12)0.05889 (13)0.0524 (5)
H10.7640−0.10330.06930.079*
O20.84059 (14)−0.17448 (10)0.19926 (10)0.0380 (4)
O30.91541 (18)−0.04074 (11)0.11696 (11)0.0491 (5)
H30.8984−0.08580.14010.074*
O40.64852 (19)0.39272 (12)0.29256 (12)0.0552 (5)
H40.71000.40200.31610.083*
O50.81123 (18)0.51420 (12)0.01735 (13)0.0559 (5)
H50.86790.5214−0.01180.084*
O60.1664 (2)0.9510 (2)0.11289 (16)0.1016 (10)
H6D0.09260.95190.10580.122*
H7A0.44710.41800.43650.122*
H6C0.19890.99330.09210.122*
H7B0.52680.42940.37560.122*
O70.5037 (2)0.44817 (18)0.42014 (16)0.0821 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.077 (2)0.0443 (14)0.0584 (17)−0.0088 (15)0.0047 (17)0.0012 (14)
C20.0428 (15)0.0536 (16)0.0674 (19)0.0066 (13)0.0042 (14)0.0095 (15)
C30.0435 (14)0.0405 (13)0.0469 (15)0.0016 (11)0.0028 (12)0.0015 (12)
C40.0392 (14)0.0479 (14)0.0489 (15)−0.0018 (11)−0.0019 (12)0.0084 (12)
C50.0513 (16)0.0557 (15)0.0385 (14)0.0009 (13)0.0068 (12)0.0082 (12)
C60.0470 (15)0.0483 (14)0.0359 (13)0.0034 (12)0.0053 (12)−0.0002 (11)
C70.0348 (12)0.0427 (13)0.0326 (12)−0.0015 (10)−0.0013 (11)−0.0019 (10)
C80.0348 (12)0.0408 (13)0.0354 (12)−0.0015 (10)−0.0010 (11)−0.0029 (11)
C90.0441 (15)0.0518 (15)0.0399 (14)−0.0022 (12)−0.0043 (12)−0.0057 (13)
C100.0409 (13)0.0398 (12)0.0398 (14)−0.0012 (11)0.0048 (12)−0.0081 (11)
C110.0495 (15)0.0466 (14)0.0334 (13)−0.0027 (12)0.0083 (12)−0.0058 (11)
C120.0376 (13)0.0400 (12)0.0312 (12)0.0008 (11)0.0044 (10)−0.0047 (10)
C130.0391 (13)0.0484 (14)0.0477 (15)−0.0028 (11)0.0068 (12)−0.0014 (12)
C140.0329 (12)0.0419 (13)0.0329 (12)−0.0004 (10)0.0018 (10)−0.0022 (10)
C150.0482 (15)0.0442 (13)0.0325 (12)0.0013 (11)0.0102 (12)−0.0013 (11)
C160.0392 (13)0.0406 (13)0.0392 (13)−0.0002 (10)0.0073 (11)−0.0032 (11)
C170.0353 (12)0.0402 (12)0.0346 (12)−0.0016 (10)0.0010 (10)−0.0024 (10)
C180.0450 (13)0.0440 (13)0.0322 (12)−0.0006 (11)0.0014 (11)−0.0038 (11)
C190.0578 (16)0.0504 (15)0.0462 (16)−0.0017 (13)−0.0124 (14)−0.0044 (13)
C200.0724 (19)0.0519 (15)0.0312 (13)0.0021 (14)0.0074 (13)−0.0040 (12)
C210.072 (2)0.0576 (16)0.0334 (13)0.0012 (15)0.0019 (14)0.0001 (13)
C220.0397 (13)0.0500 (14)0.0345 (12)−0.0008 (11)−0.0013 (11)0.0006 (11)
C230.0420 (13)0.0451 (13)0.0349 (13)0.0025 (11)0.0070 (11)0.0045 (11)
C240.077 (2)0.0574 (17)0.0470 (16)0.0101 (16)−0.0033 (16)0.0092 (15)
C250.0437 (15)0.0515 (15)0.0639 (19)−0.0012 (13)0.0115 (14)0.0044 (15)
C260.0505 (17)0.106 (3)0.0582 (19)−0.0272 (18)0.0041 (16)0.001 (2)
C270.0484 (15)0.0363 (12)0.0478 (15)−0.0050 (11)−0.0073 (13)0.0052 (11)
C280.0482 (15)0.0462 (14)0.0442 (14)0.0077 (12)−0.0062 (13)0.0008 (12)
C290.075 (2)0.070 (2)0.067 (2)−0.0067 (18)−0.0228 (19)−0.0056 (18)
C300.068 (2)0.075 (2)0.0459 (16)0.0217 (17)0.0027 (15)−0.0087 (16)
O10.0506 (11)0.0523 (11)0.0543 (11)0.0097 (9)−0.0071 (10)0.0098 (10)
O20.0353 (8)0.0418 (9)0.0370 (9)0.0006 (7)0.0022 (8)0.0003 (8)
O30.0587 (11)0.0409 (9)0.0476 (10)0.0016 (9)0.0195 (10)−0.0005 (9)
O40.0682 (13)0.0476 (10)0.0500 (12)0.0035 (10)0.0078 (10)−0.0130 (9)
O50.0558 (13)0.0523 (11)0.0595 (12)−0.0010 (9)0.0062 (10)0.0165 (10)
O60.0586 (15)0.175 (3)0.0714 (16)0.0095 (18)0.0082 (13)0.021 (2)
O70.0564 (13)0.1091 (19)0.0807 (16)−0.0227 (13)0.0062 (12)−0.0208 (16)

Geometric parameters (Å, °)

C1—C31.540 (4)C17—C181.555 (3)
C1—H1A0.9600C17—H170.9800
C1—H1B0.9600C18—C201.537 (4)
C1—H1C0.9600C18—C191.549 (4)
C2—C31.532 (4)C19—H19A0.9600
C2—H2A0.9600C19—H19B0.9600
C2—H2B0.9600C19—H19C0.9600
C2—H2C0.9600C20—C211.534 (4)
C3—C41.543 (4)C20—H20A0.9700
C3—C81.570 (3)C20—H20B0.9700
C4—O51.427 (3)C21—C221.561 (4)
C4—C51.509 (4)C21—H21A0.9700
C4—H4A0.9800C21—H21B0.9700
C5—C61.522 (4)C22—C231.538 (4)
C5—H5A0.9700C22—H220.9800
C5—H5B0.9700C23—O21.450 (3)
C6—C71.541 (3)C23—C241.514 (4)
C6—H6A0.9700C23—C251.538 (4)
C6—H6B0.9700C24—H24A0.9600
C7—C91.555 (3)C24—H24B0.9600
C7—C141.569 (3)C24—H24C0.9600
C7—C81.577 (3)C25—C261.494 (5)
C8—C101.539 (3)C25—H25A0.9700
C8—H80.9800C25—H25B0.9700
C9—H9A0.9600C26—C271.511 (4)
C9—H9B0.9600C26—H26A0.9700
C9—H9C0.9600C26—H26B0.9700
C10—O41.433 (3)C27—O21.437 (3)
C10—C111.520 (4)C27—C281.531 (4)
C10—H100.9800C27—H270.9800
C11—C121.539 (3)C28—O11.438 (3)
C11—H11A0.9700C28—C301.509 (4)
C11—H11B0.9700C28—C291.511 (4)
C12—C131.550 (4)C29—H29A0.9600
C12—C141.562 (3)C29—H29B0.9600
C12—C181.573 (4)C29—H29C0.9600
C13—H13A0.9600C30—H30A0.9600
C13—H13B0.9600C30—H30B0.9600
C13—H13C0.9600C30—H30C0.9600
C14—C151.539 (3)O1—H10.8200
C14—H140.9800O3—H30.8200
C15—C161.516 (4)O4—H40.8200
C15—H15A0.9700O5—H50.8200
C15—H15B0.9700O6—H6D0.8537
C16—O31.436 (3)O6—H6C0.8296
C16—C171.518 (3)O7—H7A0.8443
C16—H160.9800O7—H7B0.8426
C17—C221.549 (3)
C3—C1—H1A109.5C15—C16—H16108.5
C3—C1—H1B109.5C17—C16—H16108.5
H1A—C1—H1B109.5C16—C17—C22121.2 (2)
C3—C1—H1C109.5C16—C17—C18109.29 (19)
H1A—C1—H1C109.5C22—C17—C18105.51 (18)
H1B—C1—H1C109.5C16—C17—H17106.7
C3—C2—H2A109.5C22—C17—H17106.7
C3—C2—H2B109.5C18—C17—H17106.7
H2A—C2—H2B109.5C20—C18—C19106.4 (2)
C3—C2—H2C109.5C20—C18—C17100.10 (19)
H2A—C2—H2C109.5C19—C18—C17110.8 (2)
H2B—C2—H2C109.5C20—C18—C12117.1 (2)
C2—C3—C1108.2 (2)C19—C18—C12112.3 (2)
C2—C3—C4111.7 (2)C17—C18—C12109.37 (19)
C1—C3—C4105.3 (2)C18—C19—H19A109.5
C2—C3—C8113.5 (2)C18—C19—H19B109.5
C1—C3—C8110.6 (2)H19A—C19—H19B109.5
C4—C3—C8107.3 (2)C18—C19—H19C109.5
O5—C4—C5110.8 (2)H19A—C19—H19C109.5
O5—C4—C3109.3 (2)H19B—C19—H19C109.5
C5—C4—C3114.5 (2)C21—C20—C18103.5 (2)
O5—C4—H4A107.3C21—C20—H20A111.1
C5—C4—H4A107.3C18—C20—H20A111.1
C3—C4—H4A107.3C21—C20—H20B111.1
C4—C5—C6110.9 (2)C18—C20—H20B111.1
C4—C5—H5A109.5H20A—C20—H20B109.0
C6—C5—H5A109.5C20—C21—C22106.2 (2)
C4—C5—H5B109.5C20—C21—H21A110.5
C6—C5—H5B109.5C22—C21—H21A110.5
H5A—C5—H5B108.1C20—C21—H21B110.5
C5—C6—C7113.7 (2)C22—C21—H21B110.5
C5—C6—H6A108.8H21A—C21—H21B108.7
C7—C6—H6A108.8C23—C22—C17115.7 (2)
C5—C6—H6B108.8C23—C22—C21111.0 (2)
C7—C6—H6B108.8C17—C22—C21104.0 (2)
H6A—C6—H6B107.7C23—C22—H22108.6
C6—C7—C9106.4 (2)C17—C22—H22108.6
C6—C7—C14108.0 (2)C21—C22—H22108.6
C9—C7—C14112.7 (2)O2—C23—C24107.7 (2)
C6—C7—C8108.8 (2)O2—C23—C22107.6 (2)
C9—C7—C8114.3 (2)C24—C23—C22110.7 (2)
C14—C7—C8106.43 (19)O2—C23—C25103.6 (2)
C10—C8—C3116.3 (2)C24—C23—C25111.3 (2)
C10—C8—C7108.65 (19)C22—C23—C25115.4 (2)
C3—C8—C7116.4 (2)C23—C24—H24A109.5
C10—C8—H8104.7C23—C24—H24B109.5
C3—C8—H8104.7H24A—C24—H24B109.5
C7—C8—H8104.7C23—C24—H24C109.5
C7—C9—H9A109.5H24A—C24—H24C109.5
C7—C9—H9B109.5H24B—C24—H24C109.5
H9A—C9—H9B109.5C26—C25—C23105.6 (2)
C7—C9—H9C109.5C26—C25—H25A110.6
H9A—C9—H9C109.5C23—C25—H25A110.6
H9B—C9—H9C109.5C26—C25—H25B110.6
O4—C10—C11108.2 (2)C23—C25—H25B110.6
O4—C10—C8114.3 (2)H25A—C25—H25B108.7
C11—C10—C8110.8 (2)C25—C26—C27107.1 (2)
O4—C10—H10107.8C25—C26—H26A110.3
C11—C10—H10107.8C27—C26—H26A110.3
C8—C10—H10107.8C25—C26—H26B110.3
C10—C11—C12115.8 (2)C27—C26—H26B110.3
C10—C11—H11A108.3H26A—C26—H26B108.5
C12—C11—H11A108.3O2—C27—C26105.5 (2)
C10—C11—H11B108.3O2—C27—C28109.2 (2)
C12—C11—H11B108.3C26—C27—C28116.4 (3)
H11A—C11—H11B107.4O2—C27—H27108.5
C11—C12—C13107.6 (2)C26—C27—H27108.5
C11—C12—C14107.51 (19)C28—C27—H27108.5
C13—C12—C14113.0 (2)O1—C28—C30110.1 (2)
C11—C12—C18111.0 (2)O1—C28—C29105.9 (2)
C13—C12—C18110.0 (2)C30—C28—C29110.6 (3)
C14—C12—C18107.74 (19)O1—C28—C27109.7 (2)
C12—C13—H13A109.5C30—C28—C27110.4 (2)
C12—C13—H13B109.5C29—C28—C27110.1 (3)
H13A—C13—H13B109.5C28—C29—H29A109.5
C12—C13—H13C109.5C28—C29—H29B109.5
H13A—C13—H13C109.5H29A—C29—H29B109.5
H13B—C13—H13C109.5C28—C29—H29C109.5
C15—C14—C12111.37 (19)H29A—C29—H29C109.5
C15—C14—C7115.3 (2)H29B—C29—H29C109.5
C12—C14—C7116.13 (19)C28—C30—H30A109.5
C15—C14—H14104.1C28—C30—H30B109.5
C12—C14—H14104.1H30A—C30—H30B109.5
C7—C14—H14104.1C28—C30—H30C109.5
C16—C15—C14112.2 (2)H30A—C30—H30C109.5
C16—C15—H15A109.2H30B—C30—H30C109.5
C14—C15—H15A109.2C28—O1—H1109.5
C16—C15—H15B109.2C27—O2—C23109.80 (19)
C14—C15—H15B109.2C16—O3—H3109.5
H15A—C15—H15B107.9C10—O4—H4109.5
O3—C16—C15107.9 (2)C4—O5—H5109.5
O3—C16—C17114.01 (19)H6D—O6—H6C111.9
C15—C16—C17109.1 (2)H7A—O7—H7B109.7
O3—C16—H16108.5
C2—C3—C4—O553.7 (3)O3—C16—C17—C18177.5 (2)
C1—C3—C4—O5−63.5 (3)C15—C16—C17—C18−61.8 (3)
C8—C3—C4—O5178.7 (2)C16—C17—C18—C20−173.0 (2)
C2—C3—C4—C5−71.3 (3)C22—C17—C18—C20−41.2 (3)
C1—C3—C4—C5171.5 (2)C16—C17—C18—C19−60.9 (3)
C8—C3—C4—C553.7 (3)C22—C17—C18—C1970.9 (2)
O5—C4—C5—C6177.4 (2)C16—C17—C18—C1263.4 (3)
C3—C4—C5—C6−58.4 (3)C22—C17—C18—C12−164.77 (19)
C4—C5—C6—C756.6 (3)C11—C12—C18—C2070.8 (3)
C5—C6—C7—C972.3 (3)C13—C12—C18—C20−48.2 (3)
C5—C6—C7—C14−166.4 (2)C14—C12—C18—C20−171.7 (2)
C5—C6—C7—C8−51.3 (3)C11—C12—C18—C19−52.8 (3)
C2—C3—C8—C10−56.4 (3)C13—C12—C18—C19−171.8 (2)
C1—C3—C8—C1065.4 (3)C14—C12—C18—C1964.6 (2)
C4—C3—C8—C10179.7 (2)C11—C12—C18—C17−176.3 (2)
C2—C3—C8—C773.7 (3)C13—C12—C18—C1764.7 (2)
C1—C3—C8—C7−164.5 (2)C14—C12—C18—C17−58.9 (2)
C4—C3—C8—C7−50.2 (3)C19—C18—C20—C21−71.0 (3)
C6—C7—C8—C10−176.5 (2)C17—C18—C20—C2144.4 (3)
C9—C7—C8—C1064.7 (3)C12—C18—C20—C21162.5 (2)
C14—C7—C8—C10−60.4 (2)C18—C20—C21—C22−32.0 (3)
C6—C7—C8—C349.8 (3)C16—C17—C22—C23−91.4 (3)
C9—C7—C8—C3−69.0 (3)C18—C17—C22—C23143.9 (2)
C14—C7—C8—C3165.9 (2)C16—C17—C22—C21146.6 (2)
C3—C8—C10—O4−42.3 (3)C18—C17—C22—C2121.9 (3)
C7—C8—C10—O4−176.0 (2)C20—C21—C22—C23−119.1 (3)
C3—C8—C10—C11−164.9 (2)C20—C21—C22—C176.0 (3)
C7—C8—C10—C1161.4 (3)C17—C22—C23—O253.1 (3)
O4—C10—C11—C12177.1 (2)C21—C22—C23—O2171.4 (2)
C8—C10—C11—C12−56.9 (3)C17—C22—C23—C24170.6 (2)
C10—C11—C12—C13−73.3 (3)C21—C22—C23—C24−71.2 (3)
C10—C11—C12—C1448.7 (3)C17—C22—C23—C25−61.9 (3)
C10—C11—C12—C18166.3 (2)C21—C22—C23—C2556.3 (3)
C11—C12—C14—C15174.7 (2)O2—C23—C25—C2622.3 (3)
C13—C12—C14—C15−66.7 (3)C24—C23—C25—C26−93.1 (3)
C18—C12—C14—C1555.1 (3)C22—C23—C25—C26139.7 (3)
C11—C12—C14—C7−50.7 (3)C23—C25—C26—C27−7.6 (4)
C13—C12—C14—C768.0 (3)C25—C26—C27—O2−10.2 (3)
C18—C12—C14—C7−170.30 (19)C25—C26—C27—C28−131.4 (3)
C6—C7—C14—C15−52.5 (3)O2—C27—C28—O1−59.5 (3)
C9—C7—C14—C1564.7 (3)C26—C27—C28—O159.7 (3)
C8—C7—C14—C15−169.2 (2)O2—C27—C28—C3061.9 (3)
C6—C7—C14—C12174.6 (2)C26—C27—C28—C30−178.8 (3)
C9—C7—C14—C12−68.1 (3)O2—C27—C28—C29−175.7 (2)
C8—C7—C14—C1258.0 (3)C26—C27—C28—C29−56.4 (3)
C12—C14—C15—C16−56.1 (3)C26—C27—O2—C2325.7 (3)
C7—C14—C15—C16168.9 (2)C28—C27—O2—C23151.5 (2)
C14—C15—C16—O3−177.17 (19)C24—C23—O2—C2787.9 (2)
C14—C15—C16—C1758.4 (3)C22—C23—O2—C27−152.78 (19)
O3—C16—C17—C2254.6 (3)C25—C23—O2—C27−30.1 (2)
C15—C16—C17—C22175.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7B···O40.842.052.836 (3)155
O6—H6C···O5i0.832.242.791 (3)124
O7—H7A···O1ii0.842.022.829 (3)160
O6—H6D···O3iii0.852.042.879 (3)167
O5—H5···O7iv0.821.922.734 (3)174
O4—H4···O6v0.822.002.795 (3)164
O3—H3···O20.821.822.627 (2)170
O1—H1···O30.822.142.938 (3)164

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x−1, y+1, z; (iv) −x+3/2, −y+1, z−1/2; (v) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5154).

References

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  • Shi, Q., Hen, K., Jioka, T. & Mhiwada, Y. (1992). J. Nat. Prod.55, 1488–1497. [PubMed]
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  • Yu, C., Fu, H., Yu, X., Han, B. & Zhu, M. (2007). Arzneimittelforschung, 111, 568–572. [PubMed]

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