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

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ISSN: 2056-9890

Ethyl ent-15α-[(2-meth­­oxy­benz­yl­oxy)meth­yl]-16-oxobeyeran-20-oate

aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and bDepartment of Chemistry, New Drug Research & Development Center, Zhengzhou University, Zhengzhou 450052, People's Republic of China
*Correspondence e-mail: wuya0723@126.com

(Received 9 January 2012; accepted 15 January 2012; online 21 January 2012)

The title compound, C31H44O5, was synthesized from isostev­iol (systematic name: ent-16-ketobeyeran-19-oic acid). In the mol­ecule, 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.

Related literature

For background to isosteviol derivatives, see: Kinghorn et al. (1984[Kinghorn, A. D., Soejarto, D. D., Nanayakkara, N. P. D., Compadre, C. M., Makapugay, H. C., Hovanec, J. M., Medon, P. J. & Kamath, S. K. (1984). J. Nat. Prod. 47, 439-444.]); Yasukawa et al. (2002[Yasukawa, K., Kitanaka, S. & Seo, S. (2002). Biol. Pharm. Bull. 25, 1488-1490.]); Lin et al. (2004[Lin, L.-H., Lee, L.-W., Sheu, S.-Y. & Lin, P.-Y. (2004). Chem. Pharm. Bull. 52, 1117-1122.]); Roy et al. (2007[Roy, A., Roberts, F. G., Wilderman, P. R., Zhou, K., Peters, R. J. & Coates, R. M. (2007). J. Am. Chem. Soc. 129, 12453-12460.]); Li et al. (2011[Li, J., Zhang, D.-Y. & Wu, X.-M. (2011). Bioorg. Med. Chem. Lett. 21, 130-132.]). For a related structure, see: Shi (2010[Shi, H. (2010). Acta Cryst. E66, o154.]).

[Scheme 1]

Experimental

Crystal data
  • C31H44O5

  • Mr = 496.66

  • Orthorhombic, P 21 21 21

  • a = 8.7047 (17) Å

  • b = 10.749 (2) Å

  • c = 29.653 (6) Å

  • V = 2774.5 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.20 × 0.18 × 0.17 mm

Data collection
  • Rgaku R-AXIS-IV diffractometer

  • Absorption correction: multi-scan (RAXIS; Rigaku, 2004[Rigaku (2004). RAXIS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.984, Tmax = 0.987

  • 8377 measured reflections

  • 2876 independent reflections

  • 2419 reflections with I > 2σ(I)

  • Rint = 0.102

Refinement
  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.172

  • S = 1.08

  • 2876 reflections

  • 326 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: RAXIS (Rigaku, 2004[Rigaku (2004). RAXIS. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAXIS; data reduction: RAXIS; 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: SHELXL97.

Supporting information


Comment top

Isosteviol (ent-16-ketobeyeran-19-oic acid 1) is a tetracyclic diterpenoid with a beyerane skeleton, obtained by acid hydrolysis of stevioside (Kinghorn et al., 1984). In recent years, isosteviol derivatives have attracted scientific attention because of their remarkably broad spectrum of biological activities including anti-inflammatory, glucocorticoid agonist, antihypertension, antitumor, antiproliferation and inhibition of ent-kaurene synthase (Roy et al., 2007; Li et al., 2011; Yasukawa, et al., 2002). Especially, Lin and co-workers reported that isosteviol amide dimers had favorable antibacterial effects and cytotoxicity (Lin, et al., 2004), which prompted us to study new isosteviol derivatives to develop novel stronger antibacterial agents for therapeutic use. The title compound was synthesized from isosteviol. The molecule structure of the compound contains a fused four-ring system A/B/C/D and an aromatic ring (Fig. 1). The A/B ring and B/C junction are trans-fused, and C/D is cis-fused. The three six-membered rings adopt chair conformations, and the five-membered ring D adopts an envelope conformation with atom C14 displaced from the C8/C15/C16/C13 plane by 0.173 (5) Å. The C—C—C angles within the aromatic moiety cover a range 118.9 (4) - 121.4 (5) °.

Related literature top

For background to isosteviol derivatives, see: Kinghorn et al. (1984); Yasukawa et al. (2002); Lin et al. (2004); Roy et al. (2007); Li et al. (2011). For a related structure, see: Shi (2010).

Experimental top

The title compound was synthesized via esterification, Tollens reaction, 1,5-hydride shift from isosteviol, a kind of tetracyclo-diterpene, which has the skeleton of beyrane. To a stirred solution of ethyl-ent-15α-hydroxymethyl-16β-hydroxybeyeran-20-oate (0.378 g, 1 mmol) and ο-methoxybenzaldehyde (0.150 g, 1.1 mmol) in acetonitrile (10 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, at last the organic was washed with saturated NaCl aqueous solution, dried with MgSO4 and concentrated under vacuum. The residue was purified by column chromatography on silica (petroleum ether/ethyl acetate = 7:1, v/v) to give product (0.397 g, 80%). Colourless prisms 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 generated geometrically and refined as riding atoms with C-H = 0.93Å and Uiso(H) = 1.2 times Ueq(C).

Computing details top

Data collection: RAXIS (Rigaku, 2004); cell refinement: RAXIS (Rigaku, 2004); data reduction: RAXIS (Rigaku, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound, showing 30% probability ellipsolids.
Ethyl ent-15α-[(2-methoxybenzyloxy)methyl]-16-oxobeyeran-20-oate top
Crystal data top
C31H44O5Dx = 1.189 Mg m3
Mr = 496.66Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 398 reflections
a = 8.7047 (17) Åθ = 2.0–25.1°
b = 10.749 (2) ŵ = 0.08 mm1
c = 29.653 (6) ÅT = 293 K
V = 2774.5 (9) Å3Prism, colorless
Z = 40.20 × 0.18 × 0.17 mm
F(000) = 1080
Data collection top
Rgaku R-AXIS-IV
diffractometer
2876 independent reflections
Radiation source: fine-focus sealed tube2419 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.102
Detector resolution: 0 pixels mm-1θmax = 25.5°, θmin = 2.0°
Oscillation frames scansh = 1010
Absorption correction: multi-scan
(RAXIS; Rigaku, 2004)
k = 130
Tmin = 0.984, Tmax = 0.987l = 3535
8377 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)] = 0.065H-atom parameters constrained
wR(F2) = 0.172 w = 1/[σ2(Fo2) + (0.0776P)2 + 0.8183P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2876 reflectionsΔρmax = 0.21 e Å3
326 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.023 (3)
Crystal data top
C31H44O5V = 2774.5 (9) Å3
Mr = 496.66Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.7047 (17) ŵ = 0.08 mm1
b = 10.749 (2) ÅT = 293 K
c = 29.653 (6) Å0.20 × 0.18 × 0.17 mm
Data collection top
Rgaku R-AXIS-IV
diffractometer
2876 independent reflections
Absorption correction: multi-scan
(RAXIS; Rigaku, 2004)
2419 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.987Rint = 0.102
8377 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.08Δρmax = 0.21 e Å3
2876 reflectionsΔρmin = 0.19 e Å3
326 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
C10.6951 (6)1.1089 (5)0.18318 (14)0.0701 (13)
H1A0.66941.02270.18920.084*
H1B0.59991.15310.17750.084*
C20.7708 (7)1.1638 (5)0.22472 (15)0.0803 (16)
H2A0.70391.15260.25060.096*
H2B0.78621.25230.22030.096*
C30.9233 (7)1.1021 (6)0.23378 (15)0.0860 (17)
H3A0.97141.14330.25920.103*
H3B0.90471.01640.24240.103*
C41.0369 (6)1.1032 (4)0.19387 (14)0.0654 (13)
C50.9523 (6)1.0518 (4)0.15150 (13)0.0550 (11)
H5A0.92420.96680.16010.066*
C61.0479 (5)1.0346 (4)0.10860 (13)0.0571 (11)
H6A1.14680.99870.11630.068*
H6B1.06571.11480.09460.068*
C70.9642 (5)0.9495 (4)0.07574 (13)0.0535 (10)
H7A0.95060.86870.08980.064*
H7B1.02780.93800.04920.064*
C80.8081 (5)0.9983 (3)0.06108 (12)0.0455 (9)
C90.7129 (5)1.0364 (4)0.10343 (13)0.0520 (10)
H9A0.68910.95740.11830.062*
C100.7951 (5)1.1146 (4)0.14039 (12)0.0524 (10)
C110.5552 (6)1.0883 (5)0.08938 (16)0.0675 (12)
H11A0.56891.17190.07780.081*
H11B0.49021.09350.11590.081*
C120.4735 (6)1.0101 (6)0.05366 (19)0.0787 (15)
H12A0.42950.93710.06790.094*
H12B0.39001.05830.04090.094*
C130.5823 (5)0.9684 (5)0.01536 (16)0.0644 (12)
C140.7142 (5)0.8984 (4)0.03641 (15)0.0609 (11)
H14A0.67700.83610.05740.073*
H14B0.77580.85780.01350.073*
C150.8105 (5)1.1029 (3)0.02504 (12)0.0477 (9)
H15A0.80711.18370.04030.057*
C160.6624 (5)1.0851 (4)0.00128 (14)0.0560 (11)
C170.4945 (7)0.9018 (7)0.0217 (2)0.102 (2)
H17A0.56460.87660.04500.153*
H17B0.44460.82970.00940.153*
H17C0.41880.95690.03420.153*
C180.8167 (6)1.2505 (4)0.12605 (14)0.0586 (11)
H18A0.71841.28670.11950.088*
H18B0.86481.29600.15010.088*
H18C0.88041.25390.09970.088*
C191.1743 (7)1.0177 (5)0.20565 (17)0.0872 (17)
H19A1.22661.04990.23170.131*
H19B1.13750.93530.21200.131*
H19C1.24411.01480.18060.131*
C201.1039 (7)1.2327 (5)0.18884 (16)0.0714 (14)
C211.2797 (9)1.3612 (6)0.1511 (2)0.104 (2)
H21A1.32691.36460.12150.125*
H21B1.20071.42480.15230.125*
C221.3986 (7)1.3888 (7)0.1861 (3)0.107 (2)
H22A1.44101.47000.18080.160*
H22B1.35231.38650.21540.160*
H22C1.47891.32780.18440.160*
C230.9449 (5)1.1021 (4)0.00794 (13)0.0568 (11)
H23A1.04141.10250.00840.068*
H23B0.94131.17550.02690.068*
C241.0648 (5)0.9751 (5)0.06169 (15)0.0675 (13)
H24A1.09821.05440.07390.081*
H24B1.14750.94180.04340.081*
C251.0298 (5)0.8865 (4)0.09980 (13)0.0531 (10)
C261.1467 (6)0.8589 (4)0.12974 (14)0.0591 (11)
C271.1178 (8)0.7817 (5)0.16676 (16)0.0742 (15)
H27A1.19550.76410.18730.089*
C280.9741 (8)0.7323 (5)0.17255 (18)0.0797 (16)
H28A0.95480.68030.19700.096*
C290.8599 (7)0.7585 (5)0.14303 (18)0.0794 (15)
H29A0.76260.72450.14710.095*
C300.8885 (6)0.8363 (4)0.10678 (15)0.0628 (12)
H30A0.80940.85450.08680.075*
C311.4097 (7)0.8958 (7)0.1493 (2)0.107 (2)
H31A1.49900.93570.13700.160*
H31B1.43020.80880.15350.160*
H31C1.38480.93280.17790.160*
O11.0710 (5)1.3189 (4)0.21179 (17)0.1141 (16)
O21.2094 (5)1.2413 (3)0.15713 (12)0.0875 (11)
O30.6178 (5)1.1533 (4)0.03115 (11)0.0841 (11)
O40.9339 (3)0.9930 (3)0.03482 (9)0.0578 (8)
O51.2847 (4)0.9107 (4)0.11943 (11)0.0820 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.095 (3)0.067 (3)0.048 (2)0.006 (3)0.029 (2)0.004 (2)
C20.110 (4)0.087 (3)0.045 (2)0.020 (3)0.023 (3)0.003 (2)
C30.130 (5)0.091 (4)0.037 (2)0.012 (4)0.007 (3)0.002 (2)
C40.097 (3)0.060 (3)0.040 (2)0.017 (3)0.003 (2)0.001 (2)
C50.081 (3)0.046 (2)0.038 (2)0.009 (2)0.000 (2)0.0034 (17)
C60.068 (3)0.061 (2)0.042 (2)0.014 (2)0.001 (2)0.005 (2)
C70.067 (3)0.048 (2)0.045 (2)0.010 (2)0.011 (2)0.0031 (18)
C80.061 (2)0.0369 (18)0.0387 (19)0.0005 (19)0.0095 (18)0.0003 (15)
C90.064 (2)0.045 (2)0.047 (2)0.001 (2)0.015 (2)0.0057 (17)
C100.077 (3)0.044 (2)0.0363 (19)0.004 (2)0.014 (2)0.0018 (16)
C110.063 (3)0.077 (3)0.062 (3)0.002 (3)0.018 (2)0.009 (2)
C120.063 (3)0.096 (4)0.077 (3)0.006 (3)0.012 (3)0.008 (3)
C130.057 (3)0.071 (3)0.065 (3)0.008 (2)0.008 (2)0.014 (2)
C140.079 (3)0.048 (2)0.056 (2)0.011 (2)0.014 (2)0.006 (2)
C150.066 (2)0.0367 (18)0.0406 (19)0.001 (2)0.0022 (19)0.0032 (16)
C160.060 (2)0.063 (3)0.045 (2)0.012 (2)0.0022 (19)0.009 (2)
C170.076 (3)0.129 (5)0.100 (4)0.024 (4)0.000 (3)0.040 (4)
C180.081 (3)0.046 (2)0.049 (2)0.009 (2)0.001 (2)0.0032 (18)
C190.122 (5)0.081 (3)0.059 (3)0.032 (3)0.030 (3)0.003 (3)
C200.089 (4)0.068 (3)0.058 (3)0.014 (3)0.007 (3)0.016 (2)
C210.146 (6)0.072 (3)0.093 (4)0.019 (4)0.001 (4)0.007 (3)
C220.094 (4)0.090 (4)0.137 (6)0.006 (4)0.010 (4)0.002 (4)
C230.071 (3)0.054 (2)0.045 (2)0.021 (2)0.002 (2)0.0006 (19)
C240.063 (3)0.090 (3)0.050 (2)0.013 (3)0.012 (2)0.015 (2)
C250.064 (3)0.055 (2)0.040 (2)0.002 (2)0.000 (2)0.0003 (18)
C260.071 (3)0.065 (3)0.041 (2)0.008 (2)0.003 (2)0.006 (2)
C270.112 (4)0.064 (3)0.047 (2)0.023 (3)0.010 (3)0.001 (2)
C280.110 (4)0.071 (3)0.058 (3)0.013 (3)0.019 (3)0.016 (3)
C290.093 (4)0.068 (3)0.078 (3)0.001 (3)0.024 (3)0.013 (3)
C300.071 (3)0.062 (2)0.055 (2)0.002 (2)0.004 (2)0.007 (2)
C310.097 (4)0.124 (5)0.099 (4)0.009 (4)0.051 (4)0.005 (4)
O10.114 (3)0.094 (3)0.134 (4)0.007 (3)0.024 (3)0.064 (3)
O20.128 (3)0.067 (2)0.067 (2)0.001 (2)0.009 (2)0.0072 (17)
O30.099 (3)0.095 (2)0.0579 (19)0.024 (2)0.0141 (19)0.0073 (19)
O40.0654 (17)0.0623 (17)0.0456 (15)0.0147 (15)0.0147 (13)0.0140 (13)
O50.072 (2)0.115 (3)0.0582 (19)0.008 (2)0.0214 (17)0.011 (2)
Geometric parameters (Å, º) top
C1—C21.516 (7)C15—H15A0.9800
C1—C101.540 (5)C16—O31.213 (5)
C1—H1A0.9700C17—H17A0.9600
C1—H1B0.9700C17—H17B0.9600
C2—C31.508 (7)C17—H17C0.9600
C2—H2A0.9700C18—H18A0.9600
C2—H2B0.9700C18—H18B0.9600
C3—C41.542 (7)C18—H18C0.9600
C3—H3A0.9700C19—H19A0.9600
C3—H3B0.9700C19—H19B0.9600
C4—C201.517 (8)C19—H19C0.9600
C4—C191.549 (7)C20—O11.184 (6)
C4—C51.558 (6)C20—O21.317 (6)
C5—C61.531 (6)C21—O21.438 (7)
C5—C101.560 (6)C21—C221.495 (9)
C5—H5A0.9800C21—H21A0.9700
C6—C71.522 (6)C21—H21B0.9700
C6—H6A0.9700C22—H22A0.9600
C6—H6B0.9700C22—H22B0.9600
C7—C81.520 (6)C22—H22C0.9600
C7—H7A0.9700C23—O41.422 (5)
C7—H7B0.9700C23—H23A0.9700
C8—C141.534 (6)C23—H23B0.9700
C8—C151.552 (5)C24—O41.403 (5)
C8—C91.560 (5)C24—C251.509 (6)
C9—C111.538 (7)C24—H24A0.9700
C9—C101.556 (6)C24—H24B0.9700
C9—H9A0.9800C25—C301.359 (6)
C10—C181.533 (6)C25—C261.382 (6)
C11—C121.527 (7)C26—O51.359 (6)
C11—H11A0.9700C26—C271.398 (7)
C11—H11B0.9700C27—C281.369 (8)
C12—C131.545 (7)C27—H27A0.9300
C12—H12A0.9700C28—C291.354 (8)
C12—H12B0.9700C28—H28A0.9300
C13—C141.508 (7)C29—C301.384 (7)
C13—C161.518 (7)C29—H29A0.9300
C13—C171.518 (7)C30—H30A0.9300
C14—H14A0.9700C31—O51.413 (6)
C14—H14B0.9700C31—H31A0.9600
C15—C161.519 (6)C31—H31B0.9600
C15—C231.525 (6)C31—H31C0.9600
C2—C1—C10114.1 (4)H14A—C14—H14B108.9
C2—C1—H1A108.7C16—C15—C23108.7 (3)
C10—C1—H1A108.7C16—C15—C8104.5 (3)
C2—C1—H1B108.7C23—C15—C8116.6 (3)
C10—C1—H1B108.7C16—C15—H15A108.9
H1A—C1—H1B107.6C23—C15—H15A108.9
C3—C2—C1110.9 (4)C8—C15—H15A108.9
C3—C2—H2A109.5O3—C16—C13126.1 (4)
C1—C2—H2A109.5O3—C16—C15124.8 (4)
C3—C2—H2B109.5C13—C16—C15109.1 (4)
C1—C2—H2B109.5C13—C17—H17A109.5
H2A—C2—H2B108.1C13—C17—H17B109.5
C2—C3—C4115.1 (4)H17A—C17—H17B109.5
C2—C3—H3A108.5C13—C17—H17C109.5
C4—C3—H3A108.5H17A—C17—H17C109.5
C2—C3—H3B108.5H17B—C17—H17C109.5
C4—C3—H3B108.5C10—C18—H18A109.5
H3A—C3—H3B107.5C10—C18—H18B109.5
C20—C4—C3109.2 (4)H18A—C18—H18B109.5
C20—C4—C19105.7 (5)C10—C18—H18C109.5
C3—C4—C19108.5 (4)H18A—C18—H18C109.5
C20—C4—C5115.3 (4)H18B—C18—H18C109.5
C3—C4—C5108.2 (4)C4—C19—H19A109.5
C19—C4—C5109.7 (4)C4—C19—H19B109.5
C6—C5—C4117.1 (4)H19A—C19—H19B109.5
C6—C5—C10110.7 (3)C4—C19—H19C109.5
C4—C5—C10115.6 (3)H19A—C19—H19C109.5
C6—C5—H5A103.8H19B—C19—H19C109.5
C4—C5—H5A103.8O1—C20—O2121.6 (5)
C10—C5—H5A103.8O1—C20—C4124.6 (5)
C7—C6—C5110.2 (4)O2—C20—C4113.7 (4)
C7—C6—H6A109.6O2—C21—C22112.8 (6)
C5—C6—H6A109.6O2—C21—H21A109.0
C7—C6—H6B109.6C22—C21—H21A109.0
C5—C6—H6B109.6O2—C21—H21B109.0
H6A—C6—H6B108.1C22—C21—H21B109.0
C8—C7—C6113.8 (3)H21A—C21—H21B107.8
C8—C7—H7A108.8C21—C22—H22A109.5
C6—C7—H7A108.8C21—C22—H22B109.5
C8—C7—H7B108.8H22A—C22—H22B109.5
C6—C7—H7B108.8C21—C22—H22C109.5
H7A—C7—H7B107.7H22A—C22—H22C109.5
C7—C8—C14111.8 (3)H22B—C22—H22C109.5
C7—C8—C15115.8 (3)O4—C23—C15108.2 (3)
C14—C8—C15100.7 (3)O4—C23—H23A110.1
C7—C8—C9109.6 (3)C15—C23—H23A110.1
C14—C8—C9106.6 (3)O4—C23—H23B110.1
C15—C8—C9111.8 (3)C15—C23—H23B110.1
C11—C9—C10113.9 (3)H23A—C23—H23B108.4
C11—C9—C8110.6 (3)O4—C24—C25110.3 (4)
C10—C9—C8117.7 (3)O4—C24—H24A109.6
C11—C9—H9A104.3C25—C24—H24A109.6
C10—C9—H9A104.3O4—C24—H24B109.6
C8—C9—H9A104.3C25—C24—H24B109.6
C18—C10—C1109.6 (3)H24A—C24—H24B108.1
C18—C10—C9112.1 (3)C30—C25—C26118.9 (4)
C1—C10—C9107.4 (3)C30—C25—C24123.2 (4)
C18—C10—C5111.3 (4)C26—C25—C24117.9 (4)
C1—C10—C5107.7 (3)O5—C26—C25114.7 (4)
C9—C10—C5108.6 (3)O5—C26—C27125.3 (5)
C12—C11—C9113.8 (4)C25—C26—C27119.9 (5)
C12—C11—H11A108.8C28—C27—C26119.5 (5)
C9—C11—H11A108.8C28—C27—H27A120.2
C12—C11—H11B108.8C26—C27—H27A120.2
C9—C11—H11B108.8C29—C28—C27120.6 (5)
H11A—C11—H11B107.7C29—C28—H28A119.7
C11—C12—C13112.6 (4)C27—C28—H28A119.7
C11—C12—H12A109.1C28—C29—C30119.7 (5)
C13—C12—H12A109.1C28—C29—H29A120.2
C11—C12—H12B109.1C30—C29—H29A120.2
C13—C12—H12B109.1C25—C30—C29121.4 (5)
H12A—C12—H12B107.8C25—C30—H30A119.3
C14—C13—C16101.3 (3)C29—C30—H30A119.3
C14—C13—C17116.6 (4)O5—C31—H31A109.5
C16—C13—C17112.7 (4)O5—C31—H31B109.5
C14—C13—C12107.9 (4)H31A—C31—H31B109.5
C16—C13—C12106.3 (4)O5—C31—H31C109.5
C17—C13—C12111.2 (4)H31A—C31—H31C109.5
C13—C14—C8104.7 (3)H31B—C31—H31C109.5
C13—C14—H14A110.8C20—O2—C21116.6 (4)
C8—C14—H14A110.8C24—O4—C23112.1 (3)
C13—C14—H14B110.8C26—O5—C31119.5 (4)
C8—C14—H14B110.8

Experimental details

Crystal data
Chemical formulaC31H44O5
Mr496.66
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)8.7047 (17), 10.749 (2), 29.653 (6)
V3)2774.5 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.18 × 0.17
Data collection
DiffractometerRgaku R-AXIS-IV
diffractometer
Absorption correctionMulti-scan
(RAXIS; Rigaku, 2004)
Tmin, Tmax0.984, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
8377, 2876, 2419
Rint0.102
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.172, 1.08
No. of reflections2876
No. of parameters326
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.19

Computer programs: RAXIS (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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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