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Acta Cryst. (2012). E68, o2342    [ doi:10.1107/S1600536812029418 ]

Ethyl ent-15[alpha]-[(2-nitrobenzyloxy)methyl]-16-oxobeyeran-20-oate

Y. Wu, X. Wang, J. Gong and J. Tao

Abstract top

In the title compound, C30H41NO6, the three six-membered rings adopt chair conformations and the stereochemistry of the A/B and B/C ring junctions are trans. The five-membered ring D adopts an envelope conformation, with the methylene C atom as the flap. The title compound was synthesized via esterification, Tollens reaction, 1,5-hydride shift from the natural tetracyclic diterpenoid isosteviol

Comment top

The natural tetracyclic diterpenoid isosteviol (ent-16-ketobeyeran-19-oic acid) and its derivatives have a remarkably broad spectrum of biological activities including anti-inflammatory (Yasukawa et al., 2002), glucocorticoid agonist (Chang et al., 2008), antihypertension (Liu et al., 2001), antitumor (Li et al., 2011), antiproliferation (Wong et al., 2006) and inhibition of ent-kaurene synthase (Roy et al., 2007). The title compound was synthesized via esterification, Tollens reaction, 1,5-hydride shift from isosteviol in order to develop a new antitumor for therapeutic use. The crystal structures of some related compounds have already been published (Wu et al., 2009, 2012).

In the title compound the three six-membered rings adopt chair conformations and the stereochemistry of the A/B and B/C ring junctions are trans. The five-membered ring D adopts an envelope conformation, with atom C14 displaced from the C8/C15/C16/C13 plane by 0.172 (2) Å.

Related literature top

For related structures, see: Wu et al. (2009, 2012). For the biological activity of the tetracyclic diterpenoid isosteviol (ent-16-ketobeyeran-19-oic acid) and its derivatives, see: Chang et al. (2008); Li et al. (2011); Liu et al. (2001); Roy et al. (2007); Wong et al. (2006); Yasukawa et al. (2002).

Experimental top

To a stirred solution of ethyl-ent-15α-hydroxymethyl-16β-hydroxybeyeran -20-oate (0.378 g, 1 mmol) and ο-nitrobenzaldehyde (0.167 g, 1.1 mmol) in acetonitrile (8 mL) was added sulfuric acid (0.1 mmol). After stirring for 4 h at room temperature, the mixture was concentrated under vacuum and extracted with CHCl3 and H2O. The organic compound was washed with a saturated aqueous solution of NaCl, dried with MgSO4 and concentrated under vacuum. The residue was purified by column chromatography on silica (petroleum ether/ethyl acetate 6:1, v/v) to give the product C30H41NO6 (0.429 g, 84%). Colorless single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.

Refinement top

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. H atoms were positioned geometrically and refined as riding atoms with Csp2—H = 0.93 Å, Cmethyl—H = 0.96 Å, Cmethylene—H = 0.97 Å, Cmethine—H = 0.98 Å; Uiso(H) = xUeq(C), where x = 1.5 for methyl H and 1.2 for all other H atoms.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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. View of the title compound, with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. A view, along the b axis, of the crystal packing.
Ethyl ent-15α-[(2-nitrobenzyloxy)methyl]-16-oxobeyeran-20-oate top
Crystal data top
C30H41NO6Dx = 1.239 Mg m−3
Mr = 511.64Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 399 reflections
a = 8.3711 (17) Åθ = 2–25.0°
b = 11.419 (2) ŵ = 0.09 mm−1
c = 28.685 (6) ÅT = 291 K
V = 2742.0 (10) Å3PRISMATIC, colorless
Z = 40.20 × 0.18 × 0.17 mm
F(000) = 1104
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer		2688 independent reflections
Radiation source: fine-focus sealed tube2350 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 0 pixels mm-1θmax = 25.0°, θmin = 1.4°
Oscillation frames scansh = −9→9
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = −13→0
Tmin = 0.983, Tmax = 0.986l = −33→33
7952 measured reflections
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)] = 0.070H-atom parameters constrained
wR(F2) = 0.186 w = 1/[σ2(Fo2) + (0.107P)2 + 0.9805P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
2688 reflectionsΔρmax = 0.18 e Å−3
335 parametersΔρmin = −0.17 e Å−3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.006 (2)
Crystal data top
C30H41NO6V = 2742.0 (10) Å3
Mr = 511.64Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.3711 (17) ŵ = 0.09 mm−1
b = 11.419 (2) ÅT = 291 K
c = 28.685 (6) Å0.20 × 0.18 × 0.17 mm
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer		2688 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		2350 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.986Rint = 0.056
7952 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.070H-atom parameters constrained
wR(F2) = 0.186Δρmax = 0.18 e Å−3
S = 1.10Δρmin = −0.17 e Å−3
2688 reflectionsAbsolute structure: ?
335 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
O10.1611 (7)0.3605 (5)0.97148 (15)0.0846 (16)
O20.6339 (6)0.2134 (3)1.23213 (12)0.0575 (11)
O30.7511 (5)0.2638 (3)1.16532 (11)0.0556 (11)
O40.5036 (5)0.4970 (3)0.96537 (11)0.0542 (11)
O50.9724 (5)0.6750 (4)0.86124 (15)0.0677 (13)
O60.8962 (6)0.4991 (4)0.87463 (16)0.0717 (13)
C10.2466 (7)0.4154 (5)1.19284 (16)0.0486 (14)
H1A0.22250.49771.19730.058*
H1B0.14640.37471.18780.058*
C20.3243 (8)0.3678 (5)1.23739 (17)0.0553 (16)
H2A0.25490.38281.26380.066*
H2B0.33820.28371.23470.066*
C30.4854 (9)0.4252 (5)1.24562 (16)0.0534 (16)
H3A0.53350.39111.27320.064*
H3B0.46900.50791.25170.064*
C40.6014 (7)0.4119 (4)1.20465 (15)0.0411 (12)
C50.5184 (7)0.4587 (4)1.15953 (14)0.0366 (11)
H5A0.49270.54031.16700.044*
C60.6193 (6)0.4677 (4)1.11497 (15)0.0376 (11)
H6A0.72400.49881.12260.045*
H6B0.63370.39021.10170.045*
C70.5394 (6)0.5462 (4)1.07967 (15)0.0368 (12)
H7A0.60650.55101.05220.044*
H7B0.53090.62441.09270.044*
C80.3731 (6)0.5052 (4)1.06500 (15)0.0351 (11)
C90.2718 (6)0.4759 (5)1.10952 (15)0.0390 (12)
H9A0.25100.55211.12400.047*
C100.3516 (6)0.4019 (4)1.14892 (15)0.0347 (11)
C110.1045 (7)0.4302 (6)1.09511 (18)0.0580 (17)
H11A0.11470.35101.08320.070*
H11B0.03630.42741.12240.070*
C120.0253 (7)0.5071 (8)1.0579 (2)0.074 (2)
H12A−0.01390.57821.07240.089*
H12B−0.06580.46581.04500.089*
C130.1400 (7)0.5402 (6)1.01787 (18)0.0572 (16)
C140.2821 (7)0.6015 (5)1.03878 (16)0.0439 (13)
H14A0.24820.66281.06000.053*
H14B0.34830.63581.01460.053*
C150.3684 (7)0.4026 (5)1.02853 (16)0.0436 (13)
H15A0.35880.32801.04520.052*
C160.2121 (8)0.4254 (6)1.00117 (17)0.0539 (15)
C170.0516 (9)0.6066 (9)0.9796 (2)0.092 (3)
H17A−0.03710.56060.96890.138*
H17B0.12300.62130.95410.138*
H17C0.01330.67970.99180.138*
C180.3684 (7)0.2712 (4)1.13629 (18)0.0451 (13)
H18A0.26480.23891.13000.068*
H18B0.41650.23001.16190.068*
H18C0.43450.26341.10910.068*
C190.7519 (9)0.4865 (6)1.2151 (2)0.0624 (17)
H19A0.80300.45771.24280.094*
H19B0.72120.56671.21960.094*
H19C0.82470.48131.18930.094*
C200.6598 (7)0.2851 (5)1.20244 (16)0.0433 (13)
C210.8085 (9)0.1435 (5)1.15962 (19)0.0641 (18)
H21A0.83880.13111.12740.077*
H21B0.72270.08951.16690.077*
C220.9494 (9)0.1178 (6)1.1906 (2)0.0694 (19)
H22A0.98240.03801.18620.104*
H22B0.91980.12971.22250.104*
H22C1.03600.16921.18270.104*
C230.5060 (8)0.3940 (5)0.99388 (17)0.0490 (14)
H23A0.60690.38851.01040.059*
H23B0.49390.32470.97470.059*
C240.6239 (7)0.4964 (5)0.93124 (18)0.0495 (14)
H24A0.62670.42100.91570.059*
H24B0.72720.51000.94560.059*
C250.5875 (7)0.5928 (5)0.89623 (15)0.0428 (13)
C260.4326 (8)0.6335 (6)0.89139 (19)0.0576 (16)
H26A0.35290.60380.91060.069*
C270.3939 (8)0.7177 (6)0.8584 (2)0.0614 (17)
H27A0.28930.74440.85610.074*
C280.5086 (9)0.7620 (6)0.82890 (19)0.0622 (17)
H28A0.48120.81670.80630.075*
C290.6655 (8)0.7244 (5)0.83320 (17)0.0496 (14)
H29A0.74530.75520.81430.060*
C300.7004 (7)0.6404 (4)0.86617 (16)0.0398 (12)
N10.8701 (6)0.6027 (4)0.86772 (14)0.0447 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.100 (4)0.095 (4)0.059 (2)−0.034 (3)−0.024 (3)−0.007 (2)
O20.074 (3)0.044 (2)0.054 (2)0.007 (2)0.004 (2)0.0114 (18)
O30.071 (3)0.050 (2)0.0460 (18)0.022 (2)0.0126 (19)0.0083 (16)
O40.074 (3)0.047 (2)0.0411 (17)0.011 (2)0.0228 (19)0.0073 (16)
O50.052 (3)0.075 (3)0.076 (3)−0.024 (3)0.006 (2)−0.005 (2)
O60.062 (3)0.063 (3)0.090 (3)0.011 (2)0.020 (3)0.003 (2)
C10.047 (3)0.055 (3)0.043 (3)0.002 (3)0.015 (2)0.005 (2)
C20.065 (4)0.062 (4)0.040 (3)0.009 (3)0.018 (3)0.011 (2)
C30.082 (4)0.046 (3)0.032 (2)0.012 (3)0.005 (3)−0.004 (2)
C40.051 (3)0.036 (3)0.036 (2)−0.003 (3)−0.006 (2)0.002 (2)
C50.044 (3)0.031 (2)0.034 (2)0.001 (2)0.002 (2)0.0024 (19)
C60.035 (3)0.037 (3)0.041 (2)−0.006 (2)0.003 (2)−0.001 (2)
C70.042 (3)0.033 (2)0.036 (2)−0.005 (2)0.004 (2)0.006 (2)
C80.034 (3)0.040 (3)0.031 (2)−0.001 (2)0.003 (2)0.003 (2)
C90.032 (3)0.049 (3)0.037 (2)0.001 (2)0.003 (2)0.004 (2)
C100.033 (3)0.039 (3)0.032 (2)−0.004 (2)0.007 (2)−0.0005 (19)
C110.032 (3)0.094 (5)0.048 (3)−0.006 (3)0.009 (2)0.015 (3)
C120.035 (3)0.128 (6)0.061 (4)0.012 (4)0.003 (3)0.012 (4)
C130.044 (3)0.083 (4)0.045 (3)0.004 (3)−0.005 (3)0.014 (3)
C140.043 (3)0.049 (3)0.039 (2)0.009 (3)0.005 (2)0.005 (2)
C150.053 (3)0.042 (3)0.036 (2)−0.006 (3)0.008 (2)0.009 (2)
C160.060 (4)0.065 (4)0.036 (2)−0.024 (3)−0.006 (3)0.007 (3)
C170.059 (4)0.147 (7)0.070 (4)0.016 (5)−0.012 (4)0.030 (5)
C180.047 (3)0.043 (3)0.045 (3)−0.006 (3)0.004 (3)0.004 (2)
C190.073 (4)0.055 (4)0.059 (3)−0.009 (3)−0.020 (3)−0.001 (3)
C200.050 (3)0.042 (3)0.038 (2)0.001 (3)−0.005 (2)0.001 (2)
C210.084 (5)0.058 (4)0.051 (3)0.027 (4)0.000 (3)−0.006 (3)
C220.059 (4)0.066 (4)0.083 (4)0.019 (4)−0.004 (4)−0.004 (3)
C230.068 (4)0.040 (3)0.039 (2)0.010 (3)0.006 (3)0.008 (2)
C240.047 (3)0.058 (3)0.043 (3)−0.001 (3)0.007 (2)0.003 (2)
C250.051 (3)0.046 (3)0.031 (2)−0.007 (3)0.004 (2)−0.004 (2)
C260.053 (4)0.072 (4)0.047 (3)−0.003 (3)0.014 (3)0.003 (3)
C270.055 (4)0.071 (4)0.058 (3)0.011 (3)−0.001 (3)0.004 (3)
C280.077 (5)0.063 (4)0.047 (3)0.011 (4)0.005 (3)0.012 (3)
C290.060 (4)0.044 (3)0.044 (3)−0.007 (3)0.010 (3)0.001 (2)
C300.048 (3)0.034 (3)0.037 (2)−0.006 (2)0.002 (2)−0.012 (2)
N10.049 (3)0.051 (3)0.034 (2)−0.006 (3)0.003 (2)−0.0093 (19)
Geometric parameters (Å, º) top
O1—C161.207 (7)C12—H12A0.9700
O2—C201.201 (6)C12—H12B0.9700
O3—C201.333 (6)C13—C141.505 (8)
O3—C211.465 (7)C13—C161.520 (9)
O4—C241.405 (6)C13—C171.525 (8)
O4—C231.432 (6)C14—H14A0.9700
O5—N11.204 (6)C14—H14B0.9700
O6—N11.219 (6)C15—C231.525 (8)
C1—C21.534 (7)C15—C161.548 (8)
C1—C101.544 (6)C15—H15A0.9800
C1—H1A0.9700C17—H17A0.9600
C1—H1B0.9700C17—H17B0.9600
C2—C31.518 (9)C17—H17C0.9600
C2—H2A0.9700C18—H18A0.9600
C2—H2B0.9700C18—H18B0.9600
C3—C41.532 (8)C18—H18C0.9600
C3—H3A0.9700C19—H19A0.9600
C3—H3B0.9700C19—H19B0.9600
C4—C201.530 (7)C19—H19C0.9600
C4—C191.550 (8)C21—C221.505 (9)
C4—C51.563 (6)C21—H21A0.9700
C5—C61.535 (6)C21—H21B0.9700
C5—C101.569 (7)C22—H22A0.9600
C5—H5A0.9800C22—H22B0.9600
C6—C71.509 (7)C22—H22C0.9600
C6—H6A0.9700C23—H23A0.9700
C6—H6B0.9700C23—H23B0.9700
C7—C81.527 (7)C24—C251.521 (7)
C7—H7A0.9700C24—H24A0.9700
C7—H7B0.9700C24—H24B0.9700
C8—C141.535 (7)C25—C261.384 (8)
C8—C91.569 (6)C25—C301.390 (7)
C8—C151.572 (7)C26—C271.388 (9)
C9—C111.551 (8)C26—H26A0.9300
C9—C101.561 (7)C27—C281.376 (9)
C9—H9A0.9800C27—H27A0.9300
C10—C181.542 (7)C28—C291.387 (9)
C11—C121.534 (9)C28—H28A0.9300
C11—H11A0.9700C29—C301.378 (7)
C11—H11B0.9700C29—H29A0.9300
C12—C131.543 (8)C30—N11.485 (7)
C20—O3—C21116.6 (4)C13—C14—H14A110.8
C24—O4—C23112.6 (4)C8—C14—H14A110.8
C2—C1—C10113.8 (5)C13—C14—H14B110.8
C2—C1—H1A108.8C8—C14—H14B110.8
C10—C1—H1A108.8H14A—C14—H14B108.9
C2—C1—H1B108.8C23—C15—C16108.6 (4)
C10—C1—H1B108.8C23—C15—C8117.6 (5)
H1A—C1—H1B107.7C16—C15—C8103.5 (4)
C3—C2—C1110.7 (5)C23—C15—H15A108.9
C3—C2—H2A109.5C16—C15—H15A108.9
C1—C2—H2A109.5C8—C15—H15A108.9
C3—C2—H2B109.5O1—C16—C13127.7 (6)
C1—C2—H2B109.5O1—C16—C15123.6 (6)
H2A—C2—H2B108.1C13—C16—C15108.7 (4)
C2—C3—C4113.6 (4)C13—C17—H17A109.5
C2—C3—H3A108.8C13—C17—H17B109.5
C4—C3—H3A108.8H17A—C17—H17B109.5
C2—C3—H3B108.8C13—C17—H17C109.5
C4—C3—H3B108.8H17A—C17—H17C109.5
H3A—C3—H3B107.7H17B—C17—H17C109.5
C20—C4—C3109.2 (4)C10—C18—H18A109.5
C20—C4—C19105.6 (5)C10—C18—H18B109.5
C3—C4—C19108.2 (5)H18A—C18—H18B109.5
C20—C4—C5115.6 (4)C10—C18—H18C109.5
C3—C4—C5108.6 (4)H18A—C18—H18C109.5
C19—C4—C5109.4 (4)H18B—C18—H18C109.5
C6—C5—C4117.9 (4)C4—C19—H19A109.5
C6—C5—C10110.8 (4)C4—C19—H19B109.5
C4—C5—C10114.5 (4)H19A—C19—H19B109.5
C6—C5—H5A103.9C4—C19—H19C109.5
C4—C5—H5A103.9H19A—C19—H19C109.5
C10—C5—H5A103.9H19B—C19—H19C109.5
C7—C6—C5110.7 (4)O2—C20—O3123.1 (5)
C7—C6—H6A109.5O2—C20—C4123.9 (5)
C5—C6—H6A109.5O3—C20—C4112.9 (4)
C7—C6—H6B109.5O3—C21—C22112.0 (5)
C5—C6—H6B109.5O3—C21—H21A109.2
H6A—C6—H6B108.1C22—C21—H21A109.2
C6—C7—C8114.0 (4)O3—C21—H21B109.2
C6—C7—H7A108.8C22—C21—H21B109.2
C8—C7—H7A108.8H21A—C21—H21B107.9
C6—C7—H7B108.8C21—C22—H22A109.5
C8—C7—H7B108.8C21—C22—H22B109.5
H7A—C7—H7B107.7H22A—C22—H22B109.5
C7—C8—C14111.6 (4)C21—C22—H22C109.5
C7—C8—C9109.5 (4)H22A—C22—H22C109.5
C14—C8—C9106.5 (4)H22B—C22—H22C109.5
C7—C8—C15115.8 (4)O4—C23—C15108.0 (4)
C14—C8—C15101.3 (4)O4—C23—H23A110.1
C9—C8—C15111.7 (4)C15—C23—H23A110.1
C11—C9—C10113.4 (4)O4—C23—H23B110.1
C11—C9—C8110.1 (4)C15—C23—H23B110.1
C10—C9—C8118.3 (4)H23A—C23—H23B108.4
C11—C9—H9A104.5O4—C24—C25108.3 (5)
C10—C9—H9A104.5O4—C24—H24A110.0
C8—C9—H9A104.5C25—C24—H24A110.0
C18—C10—C1109.9 (4)O4—C24—H24B110.0
C18—C10—C9113.1 (4)C25—C24—H24B110.0
C1—C10—C9107.0 (4)H24A—C24—H24B108.4
C18—C10—C5111.4 (4)C26—C25—C30116.3 (5)
C1—C10—C5107.9 (4)C26—C25—C24119.8 (5)
C9—C10—C5107.3 (4)C30—C25—C24123.8 (5)
C12—C11—C9112.5 (5)C25—C26—C27121.3 (6)
C12—C11—H11A109.1C25—C26—H26A119.3
C9—C11—H11A109.1C27—C26—H26A119.3
C12—C11—H11B109.1C28—C27—C26120.7 (6)
C9—C11—H11B109.1C28—C27—H27A119.6
H11A—C11—H11B107.8C26—C27—H27A119.6
C11—C12—C13112.9 (5)C27—C28—C29119.5 (6)
C11—C12—H12A109.0C27—C28—H28A120.3
C13—C12—H12A109.0C29—C28—H28A120.3
C11—C12—H12B109.0C30—C29—C28118.5 (5)
C13—C12—H12B109.0C30—C29—H29A120.8
H12A—C12—H12B107.8C28—C29—H29A120.8
C14—C13—C16102.3 (5)C29—C30—C25123.6 (5)
C14—C13—C17116.0 (6)C29—C30—N1115.2 (5)
C16—C13—C17113.3 (5)C25—C30—N1121.2 (5)
C14—C13—C12108.0 (4)O5—N1—O6124.3 (5)
C16—C13—C12105.7 (6)O5—N1—C30118.5 (5)
C17—C13—C12110.7 (5)O6—N1—C30117.2 (5)
C13—C14—C8104.7 (5)
C10—C1—C2—C356.0 (6)C9—C8—C14—C13−72.8 (5)
C1—C2—C3—C4−56.2 (6)C15—C8—C14—C1344.0 (5)
C2—C3—C4—C20−72.3 (6)C7—C8—C15—C23−30.1 (6)
C2—C3—C4—C19173.2 (5)C14—C8—C15—C2390.7 (5)
C2—C3—C4—C554.5 (6)C9—C8—C15—C23−156.3 (4)
C20—C4—C5—C6−64.0 (6)C7—C8—C15—C16−149.8 (4)
C3—C4—C5—C6172.9 (4)C14—C8—C15—C16−29.0 (5)
C19—C4—C5—C654.9 (6)C9—C8—C15—C1684.0 (4)
C20—C4—C5—C1069.0 (6)C14—C13—C16—O1−157.8 (6)
C3—C4—C5—C10−54.0 (5)C17—C13—C16—O1−32.2 (9)
C19—C4—C5—C10−172.0 (4)C12—C13—C16—O189.2 (7)
C4—C5—C6—C7−162.9 (4)C14—C13—C16—C1521.6 (5)
C10—C5—C6—C762.4 (5)C17—C13—C16—C15147.2 (5)
C5—C6—C7—C8−59.3 (5)C12—C13—C16—C15−91.4 (5)
C6—C7—C8—C14166.3 (4)C23—C15—C16—O158.8 (7)
C6—C7—C8—C948.7 (5)C8—C15—C16—O1−175.5 (5)
C6—C7—C8—C15−78.6 (5)C23—C15—C16—C13−120.7 (5)
C7—C8—C9—C11−178.2 (5)C8—C15—C16—C135.0 (5)
C14—C8—C9—C1161.1 (6)C21—O3—C20—O25.5 (8)
C15—C8—C9—C11−48.6 (6)C21—O3—C20—C4−178.2 (5)
C7—C8—C9—C10−45.6 (6)C3—C4—C20—O2−9.0 (8)
C14—C8—C9—C10−166.3 (4)C19—C4—C20—O2107.1 (6)
C15—C8—C9—C1084.0 (5)C5—C4—C20—O2−131.8 (6)
C2—C1—C10—C1868.0 (6)C3—C4—C20—O3174.7 (5)
C2—C1—C10—C9−168.8 (5)C19—C4—C20—O3−69.2 (5)
C2—C1—C10—C5−53.6 (6)C5—C4—C20—O351.9 (6)
C11—C9—C10—C1856.8 (6)C20—O3—C21—C22−79.3 (7)
C8—C9—C10—C18−74.3 (6)C24—O4—C23—C15−178.5 (4)
C11—C9—C10—C1−64.3 (6)C16—C15—C23—O453.3 (6)
C8—C9—C10—C1164.6 (4)C8—C15—C23—O4−63.6 (6)
C11—C9—C10—C5−180.0 (4)C23—O4—C24—C25166.8 (4)
C8—C9—C10—C549.0 (5)O4—C24—C25—C26−22.9 (7)
C6—C5—C10—C1869.1 (5)O4—C24—C25—C30160.5 (5)
C4—C5—C10—C18−67.2 (5)C30—C25—C26—C27−0.3 (9)
C6—C5—C10—C1−170.3 (4)C24—C25—C26—C27−177.1 (5)
C4—C5—C10—C153.4 (5)C25—C26—C27—C281.0 (10)
C6—C5—C10—C9−55.2 (5)C26—C27—C28—C29−1.8 (10)
C4—C5—C10—C9168.5 (4)C27—C28—C29—C302.1 (9)
C10—C9—C11—C12177.6 (5)C28—C29—C30—C25−1.5 (8)
C8—C9—C11—C12−47.4 (7)C28—C29—C30—N1178.5 (5)
C9—C11—C12—C1345.6 (8)C26—C25—C30—C290.6 (8)
C11—C12—C13—C14−57.4 (8)C24—C25—C30—C29177.3 (5)
C11—C12—C13—C1651.6 (7)C26—C25—C30—N1−179.3 (5)
C11—C12—C13—C17174.6 (7)C24—C25—C30—N1−2.7 (7)
C16—C13—C14—C8−40.9 (5)C29—C30—N1—O537.0 (6)
C17—C13—C14—C8−164.7 (5)C25—C30—N1—O5−143.0 (5)
C12—C13—C14—C870.4 (6)C29—C30—N1—O6−141.5 (5)
C7—C8—C14—C13167.8 (4)C25—C30—N1—O638.4 (7)
Acknowledgements top

The authors thank the Doctoral Research fund of Henan University of Traditional Chinese Medicine for financial support (No. BSJJ2009–41).

references
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