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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Dec 15;67(Pt 1):o134. doi: 10.1107/S1600536810051561

19-Benzo­yloxy-13,16-seco-ent-beyeran 13,16-lactone

Jin Cai a, Xiaoming Zha b,*
PMCID: PMC3050127  PMID: 21522644

Abstract

The title compound, C27H34O5, a beyerane-type diterpenoid prepared by peroxidation and benzoyl­ation of isosteviol, contains a fused six-membered ring system. The O atoms of the benzoic ester and the lactone are disordered with occupancy ratios of 0.6 (4):0.4 (4) and 0.6 (2):0.4 (2), respectively. Three cyclo­hexane rings have chair conformations, whereas the remaining lactone ring adopts a half-chair conformation.

Related literature

For the pharmaceutical activity of isosteviol, see: Liu et al. (2001 ▶); Braguini et al. (2003 ▶); Mizushina et al. (2005 ▶); Wong et al. (2004) ▶; Xu et al. (2007 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the synthesis of isosteviol derivatives via peroxidation and esterification, see: Chou et al. (2008 ▶); Wu et al. (2009 ▶); Chen (2010 ▶). graphic file with name e-67-0o134-scheme1.jpg

Experimental

Crystal data

  • C27H34O5

  • M r = 438.54

  • Orthorhombic, Inline graphic

  • a = 7.7425 (16) Å

  • b = 11.871 (2) Å

  • c = 25.306 (5) Å

  • V = 2325.8 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.48 × 0.46 × 0.43 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.960, T max = 0.964

  • 12234 measured reflections

  • 2362 independent reflections

  • 1500 reflections with I > 2σ(I)

  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051

  • wR(F 2) = 0.154

  • S = 1.03

  • 2362 reflections

  • 310 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051561/rn2071sup1.cif

e-67-0o134-sup1.cif (25.7KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051561/rn2071Isup2.hkl

e-67-0o134-Isup2.hkl (116.1KB, hkl)

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

Acknowledgments

We are grateful to the China Ministry of Health Foundation for Scientific Research (project No. WKJ2005–2-022) for financial support.

supplementary crystallographic information

Comment

Isosteviol, a beyerane-type tetracyclic diterpenoid obtained with stevioside by acid hydrolysis, has a broad spectrum of pharmacological activities against the diseases including hypertension, ischemia-reperfusion injury, and cancer (Wong et al., 2004; Liu et al., 2001; Xu et al., 2007; Mizushina et al., 2005). The title compound was prepared by peroxidation and benzoylation of isosteviol. The molecule contains a fused four-ring system A/B/C/D. The A/B and B/C junctions are trans-fused, and C/D is cis-fused. Six-membered rings A, B and C adopt chair conformations with puckering amplitudes Q = 0.550 (2) / 0.559 (2) / 0.581 (2) Å, θ= 179.6 (2) / 170.4 (3) / 171.8 (3) ° and φ=76 (3) / 76 (2) / 239 (3) °, while the remaining six-membered ring D adopts a half-chair conformation with puckering amplitudes Q = 0.517 (6) Å, θ = 136.0 (3)° and φ= 305 (2) °, respectively (Cremer & Pople, 1975). The bond angle of C8—C15—C14 is 111.5 (4)°. The torsion angle of C1—C2—C3—C4 is -71.8 (6)° relates to the β-orientation of the benzoyl ester group with respect to the ent-kaurane nucleus. The oxygen atoms of the benzoic ester and the lactone are disordered. O1 and O4 are the major components of the disorder. Occupancy ratios of O1/O1' and O4/O4' are 0.6 (4):0.4 (4) and 0.6 (2):0.4 (2), respectively.

Experimental

Isosteviol was obtained by acid hydrolysis of stevioside with 10% H2SO4 at 95 °C for 7 h and then recrystallization with ethanol afforded colorless crystals of isosteviol in 80% yield. To a mixture of isosteviol (10 g, 31 mmol) in 150 ml of CH3COOH, 90 ml of 30% H2O2 was added and the mixture reaction was stirred at 60°C for two days. The reaction was cooled to room temperature and poured into ice water. The crude product was filtered and purified by recrystallization with ethanol to give the intermediate 13,16-seco-ent-beyeran-19-oate 13,16-lactone (8.2 g, 80%) as white crystals.

To a mixture of 13,16-seco-ent-beyeran-19-oate 13,16-lactone (0.33 g, 0.99 mmol) in 10 ml of CH2Cl2, pyridine (0.12 ml, 1.5 mmol) and PhCOCl (0.15 ml, 1.3 mmol) was added successively. The mixture reaction was stirred at room temperature for 40 h and washed with diluted HCl, brine and saturated NaHCO3 and brine, dried (Na2SO4) and concentrated under vacuum to give the crude product. Purification of the crude product by a column chromatography (v:v petroleum ether: EtOAc= 8:1) afforded the title compound (0.28 g, 65%) as colorless crystals. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of ethanol solution at room temperature. m.p. 436–437 K; 1H NMR (300 MHz, CDCl3), δH, p.p.m.: 0.983 (s, 3H), 1.34 (s, 3H), 1.39 (s, 3H), 0.96–2.05 (m, 18H), 2.27–2.32 (d, 1H, J=13.8 Hz), 3.03–3.13 (dd, 1H, J = 18.59, 2.47 Hz), 7.47–7.52 (t, 2H, J=7.7 Hz), 7.62–7.67 (t, 2H, J=14.9 Hz), 7.99–8.02 (m, 1H); 13C NMR (75 MHz, CDCl3), δC, p.p.m.: 14.4, 18.6, 18.8, 19.6, 28.1, 28.3, 34.9, 37.9, 38.0, 38.5, 38.6, 39.8, 43.6, 45.6, 47.8, 55.9, 57.4, 128.9, 129.2, 130.3, 130.3, 134.4, 162.3, 172.2, 172.6.

Refinement

The absolute structure could not be established reliably because of insufficient anomalous scattering effects. Therefore, 1404 Friedel opposites were merged. All H atoms were placed in geometrical positions and constrained to ride on their parent atoms with C—H distances in the range 0.96–0.98 Å, and included in the final cycles of refinement using a riding model, with Uiso(H)=1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H atoms. The oxygen atoms of the benzoic ester and the lactone are disordered with occupancy ratios of 0.6 (4): 0.4 (4) and 0.6 (2): 0.4 (2), respectively.

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound with the atom-numbering scheme. H atoms have been omitted. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C27H34O5 F(000) = 944
Mr = 438.54 Dx = 1.252 Mg m−3
Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 2537 reflections
a = 7.7425 (16) Å θ = 2.4–20.3°
b = 11.871 (2) Å µ = 0.09 mm−1
c = 25.306 (5) Å T = 298 K
V = 2325.8 (8) Å3 Prism, colourless
Z = 4 0.48 × 0.46 × 0.43 mm
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Data collection

Bruker SMART CCD area-detector diffractometer 2362 independent reflections
Radiation source: fine-focus sealed tube 1500 reflections with I > 2σ(I)
graphite Rint = 0.064
phi and ω scans θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) h = −5→9
Tmin = 0.960, Tmax = 0.964 k = −14→14
12234 measured reflections l = −28→30
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051 H-atom parameters constrained
wR(F2) = 0.154 w = 1/[σ2(Fo2) + (0.0594P)2 + 1.2539P] where P = (Fo2 + 2Fc2)/3
S = 1.03 (Δ/σ)max = 0.001
2362 reflections Δρmax = 0.18 e Å−3
310 parameters Δρmin = −0.19 e Å−3
0 restraints Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods Extinction coefficient: 0.023 (3)
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
O1 0.918 (17) 0.286 (9) 0.376 (4) 0.067 (15) 0.6 (4)
O1' 0.87 (2) 0.259 (13) 0.388 (6) 0.07 (2) 0.4 (4)
O2 0.6430 (6) 0.2441 (3) 0.34276 (13) 0.0755 (11)
O3 0.5237 (5) 0.1873 (3) 0.05672 (13) 0.0754 (11)
O4 0.319 (14) 0.287 (9) 0.0949 (8) 0.087 (15) 0.6 (2)
O4' 0.388 (18) 0.324 (8) 0.0979 (18) 0.083 (18) 0.4 (2)
O5 0.8077 (6) 0.4534 (3) 0.37365 (15) 0.0865 (12)
C1 0.7924 (8) 0.2203 (4) 0.34546 (19) 0.0627 (13)
C2 0.8863 (7) 0.1252 (4) 0.31854 (18) 0.0609 (13)
C3 1.0812 (7) 0.1462 (4) 0.3150 (2) 0.0688 (15)
H3A 1.1236 0.1678 0.3496 0.083*
H3B 1.1379 0.0763 0.3052 0.083*
C4 1.1302 (7) 0.2357 (4) 0.2759 (2) 0.0733 (15)
H4A 1.2551 0.2410 0.2740 0.088*
H4B 1.0863 0.3078 0.2879 0.088*
C5 1.0590 (6) 0.2109 (5) 0.22116 (19) 0.0660 (14)
H5A 1.1146 0.1437 0.2075 0.079*
H5B 1.0879 0.2729 0.1978 0.079*
C6 0.8618 (6) 0.1932 (4) 0.22027 (17) 0.0515 (11)
C7 0.8138 (6) 0.1451 (4) 0.16440 (16) 0.0504 (11)
H7 0.8949 0.0828 0.1589 0.061*
C8 0.6345 (6) 0.0916 (4) 0.15766 (16) 0.0507 (11)
C9 0.5994 (7) 0.0101 (4) 0.20318 (16) 0.0582 (13)
H9A 0.6739 −0.0551 0.1995 0.070*
H9B 0.4808 −0.0157 0.2011 0.070*
C10 0.6299 (7) 0.0636 (4) 0.25735 (17) 0.0585 (13)
H10A 0.5532 0.1275 0.2619 0.070*
H10B 0.6049 0.0092 0.2849 0.070*
C11 0.8170 (7) 0.1023 (4) 0.26179 (17) 0.0533 (12)
H11 0.8832 0.0365 0.2502 0.064*
C12 0.8501 (7) 0.2262 (4) 0.11891 (16) 0.0631 (13)
H12A 0.7699 0.2888 0.1206 0.076*
H12B 0.9662 0.2560 0.1224 0.076*
C13 0.8323 (7) 0.1673 (4) 0.06560 (19) 0.0689 (15)
H13A 0.8412 0.2232 0.0378 0.083*
H13B 0.9274 0.1149 0.0613 0.083*
C14 0.6646 (7) 0.1041 (4) 0.05918 (18) 0.0647 (13)
C15 0.6338 (7) 0.0269 (4) 0.10523 (17) 0.0596 (12)
H15A 0.7231 −0.0304 0.1060 0.072*
H15B 0.5234 −0.0105 0.1009 0.072*
C16 0.4840 (7) 0.1744 (4) 0.15308 (18) 0.0590 (13)
H16A 0.3798 0.1352 0.1638 0.071*
H16B 0.5033 0.2343 0.1785 0.071*
C17 0.4497 (8) 0.2280 (5) 0.1007 (2) 0.0706 (15)
C18 0.8566 (9) 0.0239 (4) 0.35505 (19) 0.0830 (18)
H18A 0.9122 −0.0413 0.3405 0.124*
H18B 0.7349 0.0100 0.3582 0.124*
H18C 0.9040 0.0397 0.3893 0.124*
C19 0.6557 (9) 0.0447 (5) 0.00632 (19) 0.0854 (18)
H19A 0.6759 0.0980 −0.0215 0.128*
H19B 0.5434 0.0116 0.0020 0.128*
H19C 0.7420 −0.0133 0.0050 0.128*
C20 0.8505 (8) 0.3784 (5) 0.4017 (2) 0.0704 (14)
C21 0.8676 (7) 0.3817 (4) 0.45931 (19) 0.0642 (13)
C22 0.9247 (8) 0.2913 (5) 0.4883 (2) 0.0811 (17)
H22 0.9533 0.2242 0.4714 0.097*
C23 0.9396 (9) 0.3002 (6) 0.5427 (3) 0.0920 (19)
H23 0.9784 0.2391 0.5624 0.110*
C24 0.8976 (8) 0.3980 (6) 0.5672 (2) 0.0895 (19)
H24 0.9076 0.4035 0.6037 0.107*
C25 0.8411 (9) 0.4880 (6) 0.5388 (2) 0.0886 (18)
H25 0.8135 0.5547 0.5561 0.106*
C26 0.8243 (7) 0.4813 (5) 0.4848 (2) 0.0743 (15)
H26 0.7844 0.5428 0.4656 0.089*
C27 0.7749 (7) 0.3072 (3) 0.23161 (18) 0.0611 (13)
H27A 0.8062 0.3602 0.2046 0.092*
H27B 0.8125 0.3348 0.2654 0.092*
H27C 0.6518 0.2978 0.2319 0.092*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.07 (2) 0.064 (16) 0.067 (14) 0.010 (18) −0.005 (16) −0.014 (14)
O1' 0.07 (3) 0.06 (2) 0.07 (2) 0.01 (3) 0.00 (2) −0.01 (2)
O2 0.075 (3) 0.083 (2) 0.069 (2) 0.005 (2) 0.016 (2) −0.0057 (19)
O3 0.084 (3) 0.085 (2) 0.058 (2) 0.016 (2) 0.005 (2) 0.0064 (19)
O4 0.08 (2) 0.08 (2) 0.097 (6) 0.03 (2) −0.006 (8) 0.007 (8)
O4' 0.08 (3) 0.08 (2) 0.091 (9) 0.03 (2) 0.004 (12) 0.011 (10)
O5 0.098 (3) 0.083 (3) 0.078 (2) 0.014 (3) −0.003 (2) 0.007 (2)
C1 0.071 (4) 0.059 (3) 0.057 (3) 0.007 (3) −0.001 (3) −0.002 (3)
C2 0.071 (3) 0.053 (3) 0.059 (3) 0.007 (3) −0.001 (3) −0.003 (2)
C3 0.069 (4) 0.065 (3) 0.072 (3) 0.014 (3) −0.011 (3) −0.013 (3)
C4 0.063 (3) 0.074 (3) 0.084 (4) −0.001 (3) −0.001 (3) −0.017 (3)
C5 0.059 (3) 0.066 (3) 0.073 (3) −0.008 (3) 0.009 (3) −0.003 (3)
C6 0.052 (3) 0.047 (3) 0.055 (3) 0.000 (2) 0.008 (2) −0.002 (2)
C7 0.054 (3) 0.048 (2) 0.049 (2) 0.002 (2) 0.010 (2) −0.002 (2)
C8 0.053 (3) 0.047 (2) 0.051 (3) 0.001 (2) 0.009 (2) 0.002 (2)
C9 0.063 (3) 0.051 (3) 0.061 (3) −0.011 (2) 0.006 (2) 0.005 (2)
C10 0.065 (3) 0.055 (3) 0.056 (3) −0.006 (3) 0.008 (3) 0.012 (2)
C11 0.059 (3) 0.046 (2) 0.055 (3) 0.003 (2) 0.003 (2) 0.000 (2)
C12 0.070 (3) 0.063 (3) 0.056 (3) −0.008 (3) 0.014 (3) 0.001 (2)
C13 0.075 (4) 0.078 (3) 0.054 (3) −0.002 (3) 0.016 (3) −0.001 (3)
C14 0.067 (3) 0.073 (3) 0.054 (3) 0.005 (3) 0.011 (3) −0.003 (3)
C15 0.061 (3) 0.059 (3) 0.059 (3) 0.005 (3) 0.007 (3) −0.009 (2)
C16 0.060 (3) 0.064 (3) 0.053 (3) 0.007 (3) 0.009 (2) 0.001 (2)
C17 0.076 (4) 0.073 (4) 0.063 (3) 0.017 (3) 0.007 (3) 0.004 (3)
C18 0.116 (5) 0.065 (3) 0.068 (3) 0.011 (4) −0.011 (4) 0.011 (3)
C19 0.088 (4) 0.107 (4) 0.061 (3) 0.001 (4) 0.008 (3) −0.019 (3)
C20 0.071 (4) 0.071 (4) 0.069 (3) 0.011 (3) −0.004 (3) −0.015 (3)
C21 0.061 (3) 0.067 (3) 0.065 (3) 0.003 (3) −0.002 (3) −0.014 (3)
C22 0.085 (4) 0.080 (4) 0.079 (4) 0.005 (4) −0.011 (3) −0.012 (3)
C23 0.091 (5) 0.098 (5) 0.087 (4) −0.002 (4) −0.010 (4) 0.004 (4)
C24 0.077 (4) 0.116 (5) 0.076 (4) −0.001 (4) 0.000 (4) −0.014 (4)
C25 0.082 (4) 0.096 (4) 0.088 (4) 0.004 (4) 0.003 (4) −0.031 (4)
C26 0.069 (4) 0.077 (3) 0.076 (4) 0.005 (3) −0.001 (3) −0.018 (3)
C27 0.077 (3) 0.045 (3) 0.062 (3) 0.003 (3) 0.007 (3) 0.002 (2)
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Geometric parameters (Å, °)

O1—C20 1.38 (2) C10—H10B 0.9700
O1—C1 1.47 (9) C11—H11 0.9800
O1'—C1 1.31 (4) C12—C13 1.526 (6)
O1'—C20 1.47 (10) C12—H12A 0.9700
O2—C1 1.193 (6) C12—H12B 0.9700
O3—C17 1.341 (6) C13—C14 1.509 (7)
O3—C14 1.473 (6) C13—H13A 0.9700
O4—C17 1.24 (3) C13—H13B 0.9700
O4'—C17 1.24 (4) C14—C15 1.501 (6)
O5—C20 1.185 (6) C14—C19 1.514 (6)
C1—C2 1.505 (7) C15—H15A 0.9700
C2—C3 1.532 (8) C15—H15B 0.9700
C2—C18 1.534 (6) C16—C17 1.495 (7)
C2—C11 1.557 (6) C16—H16A 0.9700
C3—C4 1.501 (7) C16—H16B 0.9700
C3—H3A 0.9700 C18—H18A 0.9600
C3—H3B 0.9700 C18—H18B 0.9600
C4—C5 1.519 (7) C18—H18C 0.9600
C4—H4A 0.9700 C19—H19A 0.9600
C4—H4B 0.9700 C19—H19B 0.9600
C5—C6 1.541 (6) C19—H19C 0.9600
C5—H5A 0.9700 C20—C21 1.465 (7)
C5—H5B 0.9700 C21—C22 1.373 (7)
C6—C27 1.538 (6) C21—C26 1.389 (7)
C6—C11 1.546 (6) C22—C23 1.386 (8)
C6—C7 1.569 (6) C22—H22 0.9300
C7—C12 1.526 (6) C23—C24 1.355 (9)
C7—C8 1.537 (7) C23—H23 0.9300
C7—H7 0.9800 C24—C25 1.359 (8)
C8—C9 1.528 (6) C24—H24 0.9300
C8—C16 1.529 (6) C25—C26 1.375 (7)
C8—C15 1.533 (6) C25—H25 0.9300
C9—C10 1.529 (6) C26—H26 0.9300
C9—H9A 0.9700 C27—H27A 0.9600
C9—H9B 0.9700 C27—H27B 0.9600
C10—C11 1.524 (7) C27—H27C 0.9600
C10—H10A 0.9700
C20—O1—C1 115 (6) H12A—C12—H12B 108.0
C1—O1'—C20 119 (6) C14—C13—C12 113.6 (4)
C17—O3—C14 121.5 (4) C14—C13—H13A 108.8
O2—C1—O1' 113 (6) C12—C13—H13A 108.8
O2—C1—O1 123 (2) C14—C13—H13B 108.8
O1'—C1—O1 23 (6) C12—C13—H13B 108.8
O2—C1—C2 128.4 (5) H13A—C13—H13B 107.7
O1'—C1—C2 115 (3) O3—C14—C15 109.0 (4)
O1—C1—C2 108 (2) O3—C14—C13 108.0 (4)
C1—C2—C3 112.4 (4) C15—C14—C13 110.9 (4)
C1—C2—C18 104.0 (4) O3—C14—C19 104.0 (4)
C3—C2—C18 108.1 (5) C15—C14—C19 113.2 (4)
C1—C2—C11 112.4 (4) C13—C14—C19 111.5 (5)
C3—C2—C11 108.3 (4) C14—C15—C8 111.5 (4)
C18—C2—C11 111.5 (4) C14—C15—H15A 109.3
C4—C3—C2 113.8 (5) C8—C15—H15A 109.3
C4—C3—H3A 108.8 C14—C15—H15B 109.3
C2—C3—H3A 108.8 C8—C15—H15B 109.3
C4—C3—H3B 108.8 H15A—C15—H15B 108.0
C2—C3—H3B 108.8 C17—C16—C8 118.5 (4)
H3A—C3—H3B 107.7 C17—C16—H16A 107.7
C3—C4—C5 111.8 (4) C8—C16—H16A 107.7
C3—C4—H4A 109.3 C17—C16—H16B 107.7
C5—C4—H4A 109.3 C8—C16—H16B 107.7
C3—C4—H4B 109.3 H16A—C16—H16B 107.1
C5—C4—H4B 109.3 O4—C17—O4' 32.7 (15)
H4A—C4—H4B 107.9 O4—C17—O3 117.0 (11)
C4—C5—C6 113.5 (4) O4'—C17—O3 116.7 (14)
C4—C5—H5A 108.9 O4—C17—C16 119 (2)
C6—C5—H5A 108.9 O4'—C17—C16 121 (2)
C4—C5—H5B 108.9 O3—C17—C16 120.4 (5)
C6—C5—H5B 108.9 C2—C18—H18A 109.5
H5A—C5—H5B 107.7 C2—C18—H18B 109.5
C27—C6—C5 108.1 (4) H18A—C18—H18B 109.5
C27—C6—C11 112.9 (4) C2—C18—H18C 109.5
C5—C6—C11 107.9 (4) H18A—C18—H18C 109.5
C27—C6—C7 112.6 (4) H18B—C18—H18C 109.5
C5—C6—C7 107.3 (4) C14—C19—H19A 109.5
C11—C6—C7 107.8 (3) C14—C19—H19B 109.5
C12—C7—C8 110.1 (4) H19A—C19—H19B 109.5
C12—C7—C6 114.0 (4) C14—C19—H19C 109.5
C8—C7—C6 117.7 (4) H19A—C19—H19C 109.5
C12—C7—H7 104.5 H19B—C19—H19C 109.5
C8—C7—H7 104.5 O5—C20—O1 115 (5)
C6—C7—H7 104.5 O5—C20—C21 127.0 (5)
C9—C8—C16 109.2 (4) O1—C20—C21 117 (4)
C9—C8—C15 109.6 (3) O5—C20—O1' 128 (4)
C16—C8—C15 104.7 (4) O1—C20—O1' 24 (2)
C9—C8—C7 109.8 (4) C21—C20—O1' 105 (6)
C16—C8—C7 115.5 (4) C22—C21—C26 119.7 (5)
C15—C8—C7 107.8 (4) C22—C21—C20 122.7 (5)
C8—C9—C10 112.7 (4) C26—C21—C20 117.6 (5)
C8—C9—H9A 109.1 C21—C22—C23 119.8 (6)
C10—C9—H9A 109.1 C21—C22—H22 120.1
C8—C9—H9B 109.1 C23—C22—H22 120.1
C10—C9—H9B 109.1 C24—C23—C22 120.0 (6)
H9A—C9—H9B 107.8 C24—C23—H23 120.0
C11—C10—C9 109.7 (4) C22—C23—H23 120.0
C11—C10—H10A 109.7 C23—C24—C25 120.6 (6)
C9—C10—H10A 109.7 C23—C24—H24 119.7
C11—C10—H10B 109.7 C25—C24—H24 119.7
C9—C10—H10B 109.7 C24—C25—C26 120.6 (6)
H10A—C10—H10B 108.2 C24—C25—H25 119.7
C10—C11—C6 112.0 (4) C26—C25—H25 119.7
C10—C11—C2 116.6 (4) C25—C26—C21 119.2 (6)
C6—C11—C2 115.3 (4) C25—C26—H26 120.4
C10—C11—H11 103.6 C21—C26—H26 120.4
C6—C11—H11 103.6 C6—C27—H27A 109.5
C2—C11—H11 103.6 C6—C27—H27B 109.5
C13—C12—C7 111.2 (4) H27A—C27—H27B 109.5
C13—C12—H12A 109.4 C6—C27—H27C 109.5
C7—C12—H12A 109.4 H27A—C27—H27C 109.5
C13—C12—H12B 109.4 H27B—C27—H27C 109.5
C7—C12—H12B 109.4
C20—O1'—C1—O2 −51 (23) C18—C2—C11—C10 53.1 (6)
C20—O1'—C1—O1 68 (18) C1—C2—C11—C6 71.1 (6)
C20—O1'—C1—C2 148 (12) C3—C2—C11—C6 −53.7 (6)
C20—O1—C1—O2 0(15) C18—C2—C11—C6 −172.5 (4)
C20—O1—C1—O1' −73 (11) C8—C7—C12—C13 −55.7 (5)
C20—O1—C1—C2 178 (8) C6—C7—C12—C13 169.6 (4)
O2—C1—C2—C3 159.0 (5) C7—C12—C13—C14 51.1 (6)
O1'—C1—C2—C3 −44 (13) C17—O3—C14—C15 34.9 (6)
O1—C1—C2—C3 −19 (7) C17—O3—C14—C13 −85.6 (6)
O2—C1—C2—C18 −84.3 (7) C17—O3—C14—C19 155.9 (5)
O1'—C1—C2—C18 73 (13) C12—C13—C14—O3 68.0 (5)
O1—C1—C2—C18 97 (7) C12—C13—C14—C15 −51.3 (6)
O2—C1—C2—C11 36.5 (7) C12—C13—C14—C19 −178.4 (4)
O1'—C1—C2—C11 −166 (13) O3—C14—C15—C8 −61.8 (5)
O1—C1—C2—C11 −142 (7) C13—C14—C15—C8 56.8 (5)
C1—C2—C3—C4 −71.8 (6) C19—C14—C15—C8 −177.0 (5)
C18—C2—C3—C4 174.0 (4) C9—C8—C15—C14 178.9 (4)
C11—C2—C3—C4 53.0 (5) C16—C8—C15—C14 61.9 (5)
C2—C3—C4—C5 −55.2 (6) C7—C8—C15—C14 −61.6 (5)
C3—C4—C5—C6 55.2 (6) C9—C8—C16—C17 −154.6 (4)
C4—C5—C6—C27 69.4 (5) C15—C8—C16—C17 −37.3 (6)
C4—C5—C6—C11 −53.0 (5) C7—C8—C16—C17 81.1 (5)
C4—C5—C6—C7 −168.9 (4) C14—O3—C17—O4 −171 (7)
C27—C6—C7—C12 54.5 (5) C14—O3—C17—O4' 152 (9)
C5—C6—C7—C12 −64.3 (5) C14—O3—C17—C16 −11.8 (8)
C11—C6—C7—C12 179.7 (4) C8—C16—C17—O4 173 (7)
C27—C6—C7—C8 −76.6 (5) C8—C16—C17—O4' −149 (9)
C5—C6—C7—C8 164.5 (4) C8—C16—C17—O3 13.9 (8)
C11—C6—C7—C8 48.5 (5) C1—O1—C20—O5 −70 (13)
C12—C7—C8—C9 179.7 (4) C1—O1—C20—C21 121 (7)
C6—C7—C8—C9 −47.4 (5) C1—O1—C20—O1' 58 (11)
C12—C7—C8—C16 −56.3 (5) C1—O1'—C20—O5 −18 (26)
C6—C7—C8—C16 76.6 (5) C1—O1'—C20—O1 −83 (19)
C12—C7—C8—C15 60.4 (4) C1—O1'—C20—C21 152 (17)
C6—C7—C8—C15 −166.7 (4) O5—C20—C21—C22 −177.4 (6)
C16—C8—C9—C10 −76.2 (5) O1—C20—C21—C22 −9(8)
C15—C8—C9—C10 169.7 (4) O1'—C20—C21—C22 12 (9)
C7—C8—C9—C10 51.4 (5) O5—C20—C21—C26 2.3 (10)
C8—C9—C10—C11 −60.0 (5) O1—C20—C21—C26 170 (8)
C9—C10—C11—C6 61.9 (5) O1'—C20—C21—C26 −168 (9)
C9—C10—C11—C2 −162.2 (4) C26—C21—C22—C23 −0.4 (9)
C27—C6—C11—C10 70.7 (5) C20—C21—C22—C23 179.4 (6)
C5—C6—C11—C10 −169.9 (4) C21—C22—C23—C24 0.1 (10)
C7—C6—C11—C10 −54.3 (5) C22—C23—C24—C25 −0.1 (10)
C27—C6—C11—C2 −65.8 (6) C23—C24—C25—C26 0.4 (10)
C5—C6—C11—C2 53.6 (5) C24—C25—C26—C21 −0.7 (10)
C7—C6—C11—C2 169.2 (4) C22—C21—C26—C25 0.6 (9)
C1—C2—C11—C10 −63.3 (6) C20—C21—C26—C25 −179.1 (6)
C3—C2—C11—C10 171.9 (4)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2071).

References

  1. Braguini, W. L., Gomes, M. A. B., de Oliveira, B. H., Carnieri, E. G. S., Rocha, M. E. M. & de Oliveira, M. B. M. (2003). Toxicol. Lett. 143, 83–92. [DOI] [PubMed]
  2. Bruker (1999). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Chen, J. (2010). Acta Cryst. E66, o431. [DOI] [PMC free article] [PubMed]
  4. Chou, B. H., Yang, L. M., Chang, S. F., Hsu, F. L., Lo, C. H., Liaw, J. H., Liu, P. C. & Lin, S. J. (2008). J. Nat. Prod. 71, 602–607. [DOI] [PubMed]
  5. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
  6. Liu, J. C., Kao, P. E., Hsieh, M. H., Chen, Y. J. & Chen, P. (2001). Acta Cardiol. Sin. 17, 133–140.
  7. Mizushina, Y., Akihisa, T., Ukiya, M., Hamasaki, Y., Murakami-Nakai, C., Kuriyama, I., Takeuchi, T., Sugawara, F. & Yoshida, H. (2005). Life Sci. 77, 2127–2140. [DOI] [PubMed]
  8. Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
  9. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  10. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  11. Wong, K. L., Chan, P., Yang, H. Y., Hsu, F. L., Liu, I.M., Cheng, Y.W. & Cheng, J. T. (2004). Life Sci. 74, 2379–2387. [DOI] [PubMed]
  12. Wu, Y., Yang, J. H., Dai, G. F., Liu, C. J., Tian, G. Q., Ma, W. Y. & Tao, J. C. (2009). Bioorg. Med. Chem. 17, 1464–1473. [DOI] [PubMed]
  13. Xu, D. Y., Li, Y. F., Wang, J. P., Davey, A. K., Zhang, S. J. & Evans, A. M. (2007). Life Sci. 80, 269–274. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051561/rn2071sup1.cif

e-67-0o134-sup1.cif (25.7KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051561/rn2071Isup2.hkl

e-67-0o134-Isup2.hkl (116.1KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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