organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aSchool of Pharmacy, Yantai University, Yantai 264005, People's Republic of China, and bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: mqg@ytu.edu.cn

(Received 12 January 2011; accepted 7 March 2011; online 12 March 2011)

In the title compound, C30H52O5, the three six-membered rings are in chair conformations, the five-membered ring is in an envelope form and the tetra­hydro­furan ring has a conformation inter­mediate between half-chair and sofa. Intra­molecular O—H⋯O hydrogen bonds may influence the conformation of the mol­ecule. In the crystal, mol­ecules are linked by inter­molecular O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

The title compound was prepared from 20(S)-protopanaxatriol which was degraded from Panax quinquefolium saponin. For background to and the medicinal properties of Panax ginseng and Panax quinquefolium, see: Shibata et al. (1985[Shibata, S., Tanaka, L., Shoji, L. & Saito, H. (1985). Econ. Med. Res. 1, 217-284.]); Takano et al. (1999[Takano, K., Midori, T., Eiichiro, I. & Teruo, M. (1999). Cancer Lett. 147, 11-16.]); Yu et al. (2007[Yu, C., Fu, F. H., Yu, X., Han, B. & Zhu, M. (2007). Arzneimittelforschung, 57, 568-572.]); Wang et al. (2010[Wang, T., Meng, Q. G., Zhang, J. F., Bi, Y. & Jiang, N. C. (2010). Fitoterapia, 81, 783-787.]). For related structures, see: Shi et al. (1992[Shi, Q., Hen, K., Jioka, T. & Mhiwada, Y. (1992). J. Nat. Prod. pp. 1488-1497.]); Meng et al. (2010[Meng, Q.-G., Liu, L.-D., Guo, H.-M., Bi, Y. & Wang, L. (2010). Acta Cryst. E66, o3210.]).

[Scheme 1]

Experimental

Crystal data
  • C30H52O5

  • Mr = 492.72

  • Orthorhombic, P 21 21 21

  • a = 12.7918 (6) Å

  • b = 13.7842 (7) Å

  • c = 16.0902 (8) Å

  • V = 2837.1 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.54 × 0.50 × 0.50 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 16320 measured reflections

  • 3141 independent reflections

  • 2911 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.113

  • S = 1.05

  • 3141 reflections

  • 325 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O2 0.82 2.41 2.882 (3) 117
O2—H2⋯O5 0.82 1.95 2.697 (2) 152
O3—H3⋯O4i 0.82 2.12 2.929 (3) 169
O4—H4⋯O2ii 0.82 2.13 2.890 (2) 153
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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 numbers 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, protopanaxadiol and protopanaxatriol-type saponins. (3R,6R,12R,20S,24S)-20,24-Epoxy-dammarane-3,6,12,25-tetraol and (3R,12R,20S,24R)-20,24-epoxy-dammarane-3,12,25-triol are found to possess cardioprotective effect on myocardial injury induced by isoproterenol in rats (Yu et al.,2007; Wang et al., 2010). As part of our ongoing investigation of ocotillol-type compounds and their cardioprotective effect on myocardial injury, we report herein 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; Meng et al., 2010). The six-membered rings A(C11,C13,C16,C17,C18,C19), B(C13,C15,C16,C22,C32,C33), and C(C22,C24,C25,C26,C29,C32) are in chair conformations. Ring D(C8,C9,C10,C11,C19) has an envelope form with atom C11 forming the flap. The tetrahydrofuran ring has a conformation intermediate between half-chair and sofa forms. In the crystal, molecules are linked by O—H···O hydrogen bonds (Table 1) to form a three-dimensional network.

Related literature top

The title compound was prepared from 20(S)-protopanaxatriol which was degraded from Panax quinquefolium saponin. For background to and medicinal properties of Panax ginseng and Panax quinquefolium, see: Shibata et al. (1985); Takano et al. (1999); Yu et al. (2007); Wang et al. (2010). For related structures, see: Shi et al. (1992); Meng et al. (2010).

Experimental top

20(S)-protopanaxatriol was degraded from Panax quinquefolium saponin with sodium in glycerine at about 473 - 503K and seperated by silica flash chromatography. (3R,6R,12R,20S,24R)-20,24-Epoxy-dammarane-3,6,12,25-tetraol was synthesized from 20(S)-protopanaxatriol in the presence of N,N-dimethylaminopyridine, pyridine and acetic anhydride. The esters were oxidized by m-CPBA and the title compound was obtained by saponification with sodium hydroxide in DMSO and seperated by silica flash chromatography. Finally, the crystals were dried at room temperature the title compound was crystallized from ethyl acetate. Single crystals suitable for X-ray measurements were obtained by recrystallization of an acetone solution of the title compound at room temperature.

Refinement top

In the absence of significant anomalous dispersion effects the Friedel pairs were merged. All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances in the range 0.93–0.97 Å; O—H = 0.86Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl,O). The absolute configuration is based on unchanging stereochemical centers in the synthesis

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing ellipsoids drawn at the 30% probability level. H atoms are not shown.
(3R,6R,12R,20S,24R)-20,24-Epoxydammarane- 3,6,12,25-tetraol top
Crystal data top
C30H52O5F(000) = 1088
Mr = 492.72Dx = 1.154 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 8789 reflections
a = 12.7918 (6) Åθ = 2.2–28.0°
b = 13.7842 (7) ŵ = 0.08 mm1
c = 16.0902 (8) ÅT = 298 K
V = 2837.1 (2) Å3Block, colourless
Z = 40.54 × 0.50 × 0.50 mm
Data collection top
Bruker SMART CCD
diffractometer
2911 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
ϕ and ω scansh = 1415
16320 measured reflectionsk = 1617
3141 independent reflectionsl = 1719
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0809P)2 + 0.2644P]
where P = (Fo2 + 2Fc2)/3
3141 reflections(Δ/σ)max < 0.001
325 parametersΔρmax = 0.26 e Å3
6 restraintsΔρmin = 0.24 e Å3
Crystal data top
C30H52O5V = 2837.1 (2) Å3
Mr = 492.72Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.7918 (6) ŵ = 0.08 mm1
b = 13.7842 (7) ÅT = 298 K
c = 16.0902 (8) Å0.54 × 0.50 × 0.50 mm
Data collection top
Bruker SMART CCD
diffractometer
2911 reflections with I > 2σ(I)
16320 measured reflectionsRint = 0.020
3141 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0426 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.05Δρmax = 0.26 e Å3
3141 reflectionsΔρmin = 0.24 e Å3
325 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
C10.17647 (17)0.49883 (16)0.21123 (14)0.0410 (5)
H10.24350.46960.22670.049*
C20.18569 (19)0.53311 (15)0.12319 (15)0.0449 (5)
H2A0.12380.57000.10850.054*
H2B0.24570.57570.11820.054*
C30.19786 (18)0.44819 (14)0.06334 (13)0.0403 (5)
H3A0.20300.47300.00710.048*
H3B0.26250.41440.07580.048*
C40.10599 (15)0.37543 (13)0.06804 (12)0.0301 (4)
C50.00765 (18)0.42793 (16)0.03552 (15)0.0450 (5)
H5A0.00500.42290.02400.067*
H5B0.05360.39850.05900.067*
H5C0.01040.49510.05120.067*
C60.09851 (15)0.34065 (13)0.16103 (11)0.0308 (4)
H60.16500.30780.17230.037*
C70.09008 (17)0.42290 (15)0.22863 (13)0.0400 (5)
C80.0189 (2)0.4691 (2)0.23163 (19)0.0588 (7)
H8A0.02800.51060.18430.088*
H8B0.07110.41910.23090.088*
H8C0.02580.50660.28160.088*
C90.1152 (3)0.3832 (2)0.31603 (15)0.0661 (8)
H9A0.13020.43620.35280.099*
H9B0.05610.34760.33670.099*
H9C0.17480.34100.31300.099*
C100.01445 (17)0.26102 (15)0.16760 (12)0.0360 (4)
H100.05250.28700.14810.043*
C110.04459 (17)0.17408 (14)0.11425 (12)0.0362 (4)
H11A0.10930.14710.13550.043*
H11B0.00910.12480.12000.043*
C120.05889 (14)0.19643 (13)0.02208 (11)0.0282 (4)
C130.05053 (15)0.21586 (16)0.01561 (14)0.0406 (5)
H13A0.08950.25740.02090.061*
H13B0.04290.24680.06870.061*
H13C0.08700.15550.02240.061*
C140.13479 (14)0.28469 (13)0.01349 (11)0.0279 (4)
H140.20120.26150.03640.033*
C150.15847 (17)0.30546 (14)0.07854 (12)0.0363 (4)
H15A0.20950.35740.08190.044*
H15B0.09500.32780.10540.044*
C160.20003 (16)0.21773 (15)0.12529 (11)0.0344 (4)
H160.26760.19940.10130.041*
C170.12547 (14)0.13222 (13)0.11688 (11)0.0298 (4)
H170.05740.15340.13810.036*
C180.11087 (14)0.10824 (13)0.02336 (11)0.0300 (4)
C190.21614 (17)0.07853 (14)0.01680 (13)0.0385 (4)
H19A0.25560.04010.02180.058*
H19B0.25510.13570.03100.058*
H19C0.20290.04130.06610.058*
C200.04667 (18)0.01370 (14)0.02911 (13)0.0395 (5)
H20A0.02540.02700.04390.047*
H20B0.04820.02160.02300.047*
C210.1027 (2)0.04328 (15)0.09838 (14)0.0446 (5)
H21A0.15720.08390.07510.054*
H21B0.05340.08430.12780.054*
C220.15043 (17)0.03336 (14)0.15818 (12)0.0363 (4)
H220.22650.02480.15880.044*
C230.10904 (18)0.01715 (16)0.24673 (13)0.0407 (5)
C240.1500 (3)0.07978 (18)0.28034 (17)0.0605 (7)
H24A0.22500.08020.27810.091*
H24B0.12310.13190.24710.091*
H24C0.12770.08790.33690.091*
C250.0109 (2)0.0249 (2)0.25591 (16)0.0551 (6)
H25A0.04260.04610.20420.066*
H25B0.04070.03720.27140.066*
C260.0286 (3)0.0990 (3)0.3237 (2)0.0756 (9)
H26A0.08010.07590.36330.091*
H26B0.05250.16000.30040.091*
C270.0770 (2)0.11130 (18)0.36501 (14)0.0534 (6)
H270.08550.06040.40700.064*
C280.0987 (3)0.20971 (19)0.40561 (17)0.0663 (8)
C290.2120 (4)0.2150 (2)0.4350 (2)0.0942 (13)
H29A0.25790.20940.38800.141*
H29B0.22550.16290.47310.141*
H29C0.22380.27590.46230.141*
C300.0201 (4)0.2255 (3)0.4772 (2)0.1030 (14)
H30A0.02990.28900.50040.155*
H30B0.03140.17750.51950.155*
H30C0.04990.21980.45620.155*
O20.21633 (15)0.24775 (12)0.21002 (9)0.0491 (4)
H20.21760.19990.24030.074*
O30.00324 (17)0.22871 (13)0.25149 (10)0.0572 (5)
H30.04040.18520.25350.086*
O40.15864 (14)0.57985 (12)0.26633 (12)0.0549 (4)
H40.20560.61980.26050.082*
O50.14937 (13)0.09411 (11)0.29913 (9)0.0426 (4)
O10.0805 (2)0.28725 (13)0.34886 (13)0.0759 (7)
H1A0.06920.26510.30240.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0381 (10)0.0370 (10)0.0478 (11)0.0032 (9)0.0025 (9)0.0145 (10)
C20.0528 (13)0.0297 (9)0.0523 (12)0.0109 (9)0.0068 (10)0.0062 (9)
C30.0486 (11)0.0319 (9)0.0404 (10)0.0103 (9)0.0084 (9)0.0051 (9)
C40.0328 (9)0.0250 (8)0.0325 (9)0.0007 (7)0.0008 (8)0.0003 (7)
C50.0497 (12)0.0345 (10)0.0506 (12)0.0115 (9)0.0102 (10)0.0001 (9)
C60.0314 (9)0.0294 (8)0.0316 (9)0.0007 (8)0.0010 (8)0.0027 (7)
C70.0443 (11)0.0367 (10)0.0392 (10)0.0067 (9)0.0064 (9)0.0094 (8)
C80.0474 (13)0.0524 (14)0.0767 (18)0.0077 (11)0.0191 (13)0.0309 (13)
C90.101 (2)0.0597 (15)0.0372 (12)0.0213 (16)0.0000 (14)0.0098 (11)
C100.0418 (10)0.0342 (10)0.0320 (9)0.0079 (8)0.0071 (8)0.0030 (8)
C110.0455 (11)0.0275 (9)0.0356 (10)0.0072 (8)0.0075 (9)0.0016 (8)
C120.0299 (9)0.0253 (8)0.0294 (8)0.0028 (7)0.0015 (7)0.0011 (7)
C130.0282 (9)0.0448 (11)0.0488 (11)0.0021 (8)0.0024 (8)0.0086 (10)
C140.0277 (8)0.0264 (8)0.0295 (8)0.0035 (7)0.0004 (7)0.0007 (7)
C150.0470 (11)0.0305 (9)0.0315 (9)0.0093 (9)0.0028 (8)0.0016 (8)
C160.0359 (9)0.0395 (10)0.0279 (9)0.0100 (8)0.0030 (8)0.0016 (8)
C170.0286 (9)0.0328 (9)0.0279 (8)0.0036 (7)0.0001 (7)0.0026 (7)
C180.0311 (9)0.0272 (9)0.0318 (9)0.0030 (7)0.0011 (8)0.0006 (7)
C190.0437 (11)0.0328 (9)0.0390 (10)0.0067 (8)0.0070 (9)0.0011 (8)
C200.0494 (11)0.0307 (9)0.0386 (10)0.0109 (9)0.0044 (9)0.0005 (8)
C210.0600 (13)0.0328 (10)0.0411 (11)0.0061 (10)0.0015 (10)0.0038 (9)
C220.0369 (10)0.0344 (9)0.0377 (10)0.0020 (8)0.0017 (8)0.0059 (8)
C230.0485 (11)0.0377 (11)0.0359 (10)0.0063 (9)0.0050 (9)0.0084 (9)
C240.091 (2)0.0439 (13)0.0467 (13)0.0027 (13)0.0142 (14)0.0139 (11)
C250.0490 (13)0.0685 (16)0.0480 (12)0.0168 (12)0.0038 (10)0.0152 (12)
C260.0608 (17)0.091 (2)0.0746 (19)0.0033 (17)0.0135 (15)0.0000 (19)
C270.0756 (17)0.0478 (12)0.0369 (11)0.0024 (12)0.0091 (11)0.0098 (10)
C280.112 (2)0.0402 (12)0.0463 (13)0.0050 (15)0.0070 (15)0.0074 (11)
C290.161 (4)0.0472 (15)0.074 (2)0.010 (2)0.046 (2)0.0026 (15)
C300.171 (4)0.067 (2)0.071 (2)0.009 (2)0.040 (2)0.0019 (16)
O20.0687 (10)0.0474 (9)0.0311 (7)0.0241 (8)0.0123 (7)0.0037 (7)
O30.0882 (13)0.0489 (10)0.0346 (7)0.0240 (9)0.0183 (8)0.0033 (7)
O40.0598 (10)0.0438 (9)0.0610 (10)0.0155 (8)0.0113 (9)0.0241 (8)
O50.0519 (9)0.0414 (8)0.0346 (7)0.0059 (7)0.0038 (6)0.0064 (6)
O10.1141 (18)0.0473 (10)0.0663 (12)0.0204 (12)0.0115 (12)0.0160 (9)
Geometric parameters (Å, º) top
C1—O41.444 (2)C16—H160.9800
C1—C21.498 (3)C17—C221.549 (3)
C1—C71.548 (3)C17—C181.552 (2)
C1—H10.9800C17—H170.9800
C2—C31.524 (3)C18—C201.543 (2)
C2—H2A0.9700C18—C191.549 (3)
C2—H2B0.9700C19—H19A0.9600
C3—C41.547 (3)C19—H19B0.9600
C3—H3A0.9700C19—H19C0.9600
C3—H3B0.9700C20—C211.540 (3)
C4—C51.543 (3)C20—H20A0.9700
C4—C141.572 (2)C20—H20B0.9700
C4—C61.574 (3)C21—C221.554 (3)
C5—H5A0.9600C21—H21A0.9700
C5—H5B0.9600C21—H21B0.9700
C5—H5C0.9600C22—C231.536 (3)
C6—C101.540 (3)C22—H220.9800
C6—C71.575 (3)C23—O51.450 (3)
C6—H60.9800C23—C241.534 (3)
C7—C81.534 (3)C23—C251.546 (3)
C7—C91.543 (3)C24—H24A0.9600
C8—H8A0.9600C24—H24B0.9600
C8—H8B0.9600C24—H24C0.9600
C8—H8C0.9600C25—C261.510 (4)
C9—H9A0.9600C25—H25A0.9700
C9—H9B0.9600C25—H25B0.9700
C9—H9C0.9600C26—C271.515 (4)
C10—O31.428 (2)C26—H26A0.9700
C10—C111.524 (3)C26—H26B0.9700
C10—H100.9800C27—O51.427 (3)
C11—C121.526 (3)C27—C281.531 (4)
C11—H11A0.9700C27—H270.9800
C11—H11B0.9700C28—O11.425 (3)
C12—C131.549 (3)C28—C291.525 (5)
C12—C141.563 (2)C28—C301.544 (5)
C12—C181.567 (2)C29—H29A0.9600
C13—H13A0.9600C29—H29B0.9600
C13—H13B0.9600C29—H29C0.9600
C13—H13C0.9600C30—H30A0.9600
C14—C151.538 (3)C30—H30B0.9600
C14—H140.9800C30—H30C0.9600
C15—C161.520 (3)O2—H20.8200
C15—H15A0.9700O3—H30.8200
C15—H15B0.9700O4—H40.8200
C16—O21.440 (2)O1—H1A0.8200
C16—C171.522 (2)
O4—C1—C2110.43 (18)O2—C16—H16108.6
O4—C1—C7107.41 (16)C15—C16—H16108.6
C2—C1—C7116.14 (18)C17—C16—H16108.6
O4—C1—H1107.5C16—C17—C22120.91 (15)
C2—C1—H1107.5C16—C17—C18109.06 (15)
C7—C1—H1107.5C22—C17—C18104.68 (15)
C1—C2—C3111.31 (17)C16—C17—H17107.2
C1—C2—H2A109.4C22—C17—H17107.2
C3—C2—H2A109.4C18—C17—H17107.2
C1—C2—H2B109.4C20—C18—C19105.34 (16)
C3—C2—H2B109.4C20—C18—C17100.71 (15)
H2A—C2—H2B108.0C19—C18—C17110.87 (15)
C2—C3—C4112.93 (17)C20—C18—C12117.21 (15)
C2—C3—H3A109.0C19—C18—C12112.30 (15)
C4—C3—H3A109.0C17—C18—C12109.77 (15)
C2—C3—H3B109.0C18—C19—H19A109.5
C4—C3—H3B109.0C18—C19—H19B109.5
H3A—C3—H3B107.8H19A—C19—H19B109.5
C5—C4—C3107.38 (16)C18—C19—H19C109.5
C5—C4—C14112.02 (16)H19A—C19—H19C109.5
C3—C4—C14108.10 (15)H19B—C19—H19C109.5
C5—C4—C6114.56 (17)C21—C20—C18103.09 (16)
C3—C4—C6106.87 (15)C21—C20—H20A111.1
C14—C4—C6107.61 (14)C18—C20—H20A111.1
C4—C5—H5A109.5C21—C20—H20B111.1
C4—C5—H5B109.5C18—C20—H20B111.1
H5A—C5—H5B109.5H20A—C20—H20B109.1
C4—C5—H5C109.5C20—C21—C22106.51 (16)
H5A—C5—H5C109.5C20—C21—H21A110.4
H5B—C5—H5C109.5C22—C21—H21A110.4
C10—C6—C4108.96 (15)C20—C21—H21B110.4
C10—C6—C7114.70 (15)C22—C21—H21B110.4
C4—C6—C7116.19 (16)H21A—C21—H21B108.6
C10—C6—H6105.3C23—C22—C17117.05 (17)
C4—C6—H6105.3C23—C22—C21109.87 (17)
C7—C6—H6105.3C17—C22—C21104.55 (15)
C8—C7—C9107.9 (2)C23—C22—H22108.4
C8—C7—C1111.95 (19)C17—C22—H22108.4
C9—C7—C1104.9 (2)C21—C22—H22108.4
C8—C7—C6112.53 (18)O5—C23—C24108.09 (17)
C9—C7—C6111.07 (19)O5—C23—C22108.07 (16)
C1—C7—C6108.25 (16)C24—C23—C22109.6 (2)
C7—C8—H8A109.5O5—C23—C25104.3 (2)
C7—C8—H8B109.5C24—C23—C25111.5 (2)
H8A—C8—H8B109.5C22—C23—C25114.89 (19)
C7—C8—H8C109.5C23—C24—H24A109.5
H8A—C8—H8C109.5C23—C24—H24B109.5
H8B—C8—H8C109.5H24A—C24—H24B109.5
C7—C9—H9A109.5C23—C24—H24C109.5
C7—C9—H9B109.5H24A—C24—H24C109.5
H9A—C9—H9B109.5H24B—C24—H24C109.5
C7—C9—H9C109.5C26—C25—C23105.3 (2)
H9A—C9—H9C109.5C26—C25—H25A110.7
H9B—C9—H9C109.5C23—C25—H25A110.7
O3—C10—C11108.21 (17)C26—C25—H25B110.7
O3—C10—C6110.93 (17)C23—C25—H25B110.7
C11—C10—C6110.19 (16)H25A—C25—H25B108.8
O3—C10—H10109.2C25—C26—C27105.0 (2)
C11—C10—H10109.2C25—C26—H26A110.7
C6—C10—H10109.2C27—C26—H26A110.7
C10—C11—C12114.79 (16)C25—C26—H26B110.7
C10—C11—H11A108.6C27—C26—H26B110.7
C12—C11—H11A108.6H26A—C26—H26B108.8
C10—C11—H11B108.6O5—C27—C26103.5 (2)
C12—C11—H11B108.6O5—C27—C28110.3 (2)
H11A—C11—H11B107.5C26—C27—C28116.6 (3)
C11—C12—C13107.89 (16)O5—C27—H27108.7
C11—C12—C14108.52 (15)C26—C27—H27108.7
C13—C12—C14113.09 (16)C28—C27—H27108.7
C11—C12—C18110.36 (15)O1—C28—C29108.6 (3)
C13—C12—C18109.58 (15)O1—C28—C27111.2 (2)
C14—C12—C18107.41 (14)C29—C28—C27110.3 (3)
C12—C13—H13A109.5O1—C28—C30105.4 (3)
C12—C13—H13B109.5C29—C28—C30112.4 (3)
H13A—C13—H13B109.5C27—C28—C30108.9 (3)
C12—C13—H13C109.5C28—C29—H29A109.5
H13A—C13—H13C109.5C28—C29—H29B109.5
H13B—C13—H13C109.5H29A—C29—H29B109.5
C15—C14—C12110.63 (14)C28—C29—H29C109.5
C15—C14—C4115.82 (15)H29A—C29—H29C109.5
C12—C14—C4115.13 (14)H29B—C29—H29C109.5
C15—C14—H14104.6C28—C30—H30A109.5
C12—C14—H14104.6C28—C30—H30B109.5
C4—C14—H14104.6H30A—C30—H30B109.5
C16—C15—C14113.40 (16)C28—C30—H30C109.5
C16—C15—H15A108.9H30A—C30—H30C109.5
C14—C15—H15A108.9H30B—C30—H30C109.5
C16—C15—H15B108.9C16—O2—H2109.5
C14—C15—H15B108.9C10—O3—H3109.5
H15A—C15—H15B107.7C1—O4—H4109.5
O2—C16—C15106.89 (16)C27—O5—C23108.82 (18)
O2—C16—C17113.42 (15)C28—O1—H1A109.5
C15—C16—C17110.66 (15)
O4—C1—C2—C3176.51 (18)O2—C16—C17—C18178.19 (16)
C7—C1—C2—C353.9 (3)C15—C16—C17—C1858.1 (2)
C1—C2—C3—C458.2 (3)C16—C17—C18—C20172.77 (15)
C2—C3—C4—C566.8 (2)C22—C17—C18—C2042.05 (18)
C2—C3—C4—C14172.11 (17)C16—C17—C18—C1961.7 (2)
C2—C3—C4—C656.5 (2)C22—C17—C18—C1969.06 (18)
C5—C4—C6—C1066.2 (2)C16—C17—C18—C1263.00 (19)
C3—C4—C6—C10174.97 (15)C22—C17—C18—C12166.28 (14)
C14—C4—C6—C1059.06 (19)C11—C12—C18—C2066.3 (2)
C5—C4—C6—C765.2 (2)C13—C12—C18—C2052.4 (2)
C3—C4—C6—C753.6 (2)C14—C12—C18—C20175.57 (15)
C14—C4—C6—C7169.54 (15)C11—C12—C18—C1955.9 (2)
O4—C1—C7—C847.7 (3)C13—C12—C18—C19174.53 (16)
C2—C1—C7—C876.5 (2)C14—C12—C18—C1962.25 (19)
O4—C1—C7—C969.1 (2)C11—C12—C18—C17179.69 (15)
C2—C1—C7—C9166.7 (2)C13—C12—C18—C1761.64 (19)
O4—C1—C7—C6172.26 (17)C14—C12—C18—C1761.57 (18)
C2—C1—C7—C648.1 (2)C19—C18—C20—C2171.6 (2)
C10—C6—C7—C853.4 (3)C17—C18—C20—C2143.78 (19)
C4—C6—C7—C875.3 (2)C12—C18—C20—C21162.75 (17)
C10—C6—C7—C967.8 (2)C18—C20—C21—C2229.8 (2)
C4—C6—C7—C9163.6 (2)C16—C17—C22—C2390.9 (2)
C10—C6—C7—C1177.61 (18)C18—C17—C22—C23145.68 (17)
C4—C6—C7—C149.0 (2)C16—C17—C22—C21147.28 (18)
C4—C6—C10—O3178.68 (17)C18—C17—C22—C2123.9 (2)
C7—C6—C10—O346.5 (2)C20—C21—C22—C23122.8 (2)
C4—C6—C10—C1161.5 (2)C20—C21—C22—C173.6 (2)
C7—C6—C10—C11166.30 (17)C17—C22—C23—O556.9 (2)
O3—C10—C11—C12179.57 (18)C21—C22—C23—O5175.92 (17)
C6—C10—C11—C1259.0 (2)C17—C22—C23—C24174.54 (19)
C10—C11—C12—C1371.6 (2)C21—C22—C23—C2466.5 (2)
C10—C11—C12—C1451.3 (2)C17—C22—C23—C2559.0 (3)
C10—C11—C12—C18168.72 (16)C21—C22—C23—C2560.0 (3)
C11—C12—C14—C15175.74 (16)O5—C23—C25—C267.7 (3)
C13—C12—C14—C1564.6 (2)C24—C23—C25—C26108.7 (2)
C18—C12—C14—C1556.43 (19)C22—C23—C25—C26125.8 (2)
C11—C12—C14—C450.6 (2)C23—C25—C26—C2713.9 (3)
C13—C12—C14—C469.1 (2)C25—C26—C27—O530.9 (3)
C18—C12—C14—C4169.89 (14)C25—C26—C27—C28152.2 (2)
C5—C4—C14—C1560.1 (2)O5—C27—C28—O164.9 (3)
C3—C4—C14—C1558.1 (2)C26—C27—C28—O152.7 (3)
C6—C4—C14—C15173.16 (15)O5—C27—C28—C2955.5 (3)
C5—C4—C14—C1271.2 (2)C26—C27—C28—C29173.2 (3)
C3—C4—C14—C12170.70 (16)O5—C27—C28—C30179.3 (3)
C6—C4—C14—C1255.6 (2)C26—C27—C28—C3063.0 (3)
C12—C14—C15—C1654.5 (2)C26—C27—O5—C2337.5 (2)
C4—C14—C15—C16172.13 (16)C28—C27—O5—C23163.0 (2)
C14—C15—C16—O2178.89 (16)C24—C23—O5—C2790.3 (2)
C14—C15—C16—C1754.9 (2)C22—C23—O5—C27151.15 (18)
O2—C16—C17—C2260.5 (2)C25—C23—O5—C2728.5 (2)
C15—C16—C17—C22179.36 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.822.412.882 (3)117
O2—H2···O50.821.952.697 (2)152
O3—H3···O4i0.822.122.929 (3)169
O4—H4···O2ii0.822.132.890 (2)153
Symmetry codes: (i) x, y1/2, z1/2; (ii) x+1/2, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC30H52O5
Mr492.72
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)12.7918 (6), 13.7842 (7), 16.0902 (8)
V3)2837.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.54 × 0.50 × 0.50
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16320, 3141, 2911
Rint0.020
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.113, 1.05
No. of reflections3141
No. of parameters325
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.822.412.882 (3)117
O2—H2···O50.821.952.697 (2)152
O3—H3···O4i0.822.122.929 (3)169
O4—H4···O2ii0.822.132.890 (2)153
Symmetry codes: (i) x, y1/2, z1/2; (ii) x+1/2, y+1, z1/2.
 

Acknowledgements

The authors thank Mr Lian-Dong Liu (College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, People's Republic of China) for his invaluable support of the X-ray data collection. The authors would like to thank Shandong Provincial Natural Science Foundation, China (Y2007C138,Y2008B29), the Scientific Reasearch Foundation of the Higher Education Institutions of Shandong Province, China (J07WE26), the National Natural Science Foundation of China (No.81001358) and the Promotive Research Fund for Excellent Young and Middle-aged sScientisits of Shandong Province (No. BS2010YY073) for research grants.

References

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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShi, Q., Hen, K., Jioka, T. & Mhiwada, Y. (1992). J. Nat. Prod. pp. 1488–1497.  CSD CrossRef Web of Science Google Scholar
First citationShibata, S., Tanaka, L., Shoji, L. & Saito, H. (1985). Econ. Med. Res. 1, 217–284.  Google Scholar
First citationTakano, K., Midori, T., Eiichiro, I. & Teruo, M. (1999). Cancer Lett. 147, 11–16.  Web of Science PubMed Google Scholar
First citationWang, T., Meng, Q. G., Zhang, J. F., Bi, Y. & Jiang, N. C. (2010). Fitoterapia, 81, 783–787.  Web of Science CrossRef CAS PubMed Google Scholar
First citationYu, C., Fu, F. H., Yu, X., Han, B. & Zhu, M. (2007). Arzneimittelforschung, 57, 568–572.  Web of Science PubMed CAS Google Scholar

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