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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1027

3β-Acet­­oxy-12-oxoolean-28-oic acid benzyl ester

aSchool of Chemical Engineering, University of Science and Technology Liaoning, Liaoning Anshan, 114051, People's Republic of China, and bAnshan Industry Research Institute, Liaoning Anshan, 114000, People's Republic of China
*Correspondence e-mail: hjy741110@yahoo.com.cn

(Received 24 February 2011; accepted 24 March 2011; online 7 April 2011)

The mol­ecule of title compound, C39H56O5, contains five fused six-membered rings, four of which (rings A, B, D and E) adopt a chair conformation, while the other (ring C) has a half chair conformation. The acet­oxy and carb­oxy­benzyl groups occupy equatorial positions.

Related literature

For oleanolic acid derivatives, see: Honda et al. (2003[Honda, Y., Honda, T., Roy, S. & Gribble, G. W. (2003). J. Org. Chem. 68, 4991-4993.]); Liu (1995[Liu, J. (1995). J. Ethnopharmacol. 49, 57-68.]); Matsuda et al. (1999[Matsuda, H., Li, Y. H., Murakami, T., Yamahara, J. & Yoshikawa, M. (1999). Bioorg. Med. Chem. 7, 323-327.]); Sun et al. (2003[Sun, H.-X., Ye, Y.-P., Wang, K.-W. & Pan, Y.-J. (2003). Acta Cryst. E59, o989-o991.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C39H56O5

  • Mr = 604.84

  • Orthorhombic, P 21 21 21

  • a = 6.9775 (3) Å

  • b = 12.4235 (5) Å

  • c = 39.1480 (16) Å

  • V = 3393.5 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 113 K

  • 0.16 × 0.14 × 0.12 mm

Data collection
  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.])Tmin = 0.980, Tmax = 0.991

  • 31130 measured reflections

  • 4606 independent reflections

  • 4201 reflections with I > 2σ(I)

  • Rint = 0.061

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.114

  • S = 1.09

  • 4606 reflections

  • 406 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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

Oleanolic acid derivatives are triterpenoid compounds that exist widely in food, medicinal herbs and other plants (Liu, 1995; Honda et al., 2003; Matsuda et al., 1999). Recently, our laboratories have disclosed the design and synthesis of a novel series of ETA receptor selective antagonists, based on oleanolic acid derivatives. Herewith, we report the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1) bond lengths and angles are generally within normal ranges (Allen et al., 1987). It contains five cyclohexane rings [A(C1—C6), B(C5—C10), C(C7,C8,C11—C14), D(C13—C18) and E(C17—C22)]. The ring A, B, D and E take a chair conformation, and the ring C has a half-chair conformation, in which the carboxybenzyl and acetoxy groups occupy the equatorial positions.

Related literature top

For oleanolic acid derivatives, see: Honda et al. (2003); Liu (1995); Matsuda et al. (1999); Sun et al. (2003). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Commercially available oleanolic acid, benzyl bromide and K2CO3 in dry tetrahydrofuran was stirred at room temperature overnight to give benzyl ester in 91% yield. Reaction of benzyl ester with acetic anhydride in dry pyridine gave acetyl oleanolic acid benzyl ester in 96% yield. Treatment of acetyl oleanolic acid benzyl ester with 1,4-dioxane-acetic acid mixture, followed by adding the solution of H2O2 in acetic acid, afforded the title compound (yield 64% after column chromatography purification). Crystals suitable for X-ray structure analysis were obtained by slow evaporation of a solution in methanol at room temperature.

Refinement top

The absolute configuration could not be established because of the absence of significant anomalous effects and has been assigned arbitrary. Friedel pairs were merged. H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.95–1.00 Å and Uiso(H) =1.2Ueq(parent) or 1.5Ueq(parent).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 molecule of C39H56O5 showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 35% probability level. H atoms are omitted for clarity.
3β-Acetoxy-12-oxoolean-28-oic acid benzyl ester top
Crystal data top
C39H56O5F(000) = 1320
Mr = 604.84Dx = 1.184 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6474 reflections
a = 6.9775 (3) Åθ = 1.7–27.9°
b = 12.4235 (5) ŵ = 0.08 mm1
c = 39.1480 (16) ÅT = 113 K
V = 3393.5 (2) Å3Block, colourless
Z = 40.16 × 0.14 × 0.12 mm
Data collection top
Rigaku Saturn
diffractometer
4606 independent reflections
Radiation source: rotating anode4201 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.061
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.7°
ω scansh = 89
Absorption correction: multi-scan
CrystalClear
k = 1616
Tmin = 0.980, Tmax = 0.991l = 4851
31130 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)] = 0.050H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0532P)2 + 0.4893P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
4606 reflectionsΔρmax = 0.24 e Å3
406 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0053 (7)
Crystal data top
C39H56O5V = 3393.5 (2) Å3
Mr = 604.84Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.9775 (3) ŵ = 0.08 mm1
b = 12.4235 (5) ÅT = 113 K
c = 39.1480 (16) Å0.16 × 0.14 × 0.12 mm
Data collection top
Rigaku Saturn
diffractometer
4606 independent reflections
Absorption correction: multi-scan
CrystalClear
4201 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.991Rint = 0.061
31130 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.09Δρmax = 0.24 e Å3
4606 reflectionsΔρmin = 0.18 e Å3
406 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
O10.9465 (2)0.71768 (14)0.64283 (4)0.0274 (4)
O21.2672 (3)0.74643 (14)0.64732 (5)0.0335 (4)
O30.6349 (3)0.89260 (13)0.85384 (4)0.0277 (4)
O40.3626 (3)0.60770 (14)0.90948 (5)0.0315 (4)
O50.5121 (3)0.45703 (13)0.92650 (5)0.0314 (4)
C10.7536 (4)0.80684 (18)0.72827 (6)0.0250 (5)
H1A0.65800.86290.73400.030*
H1B0.87700.82800.73880.030*
C20.7781 (4)0.80269 (19)0.68926 (6)0.0267 (5)
H2A0.65330.78700.67830.032*
H2B0.82360.87330.68080.032*
C30.9216 (4)0.71608 (18)0.67993 (5)0.0242 (5)
H31.04710.73330.69100.029*
C40.8594 (4)0.60222 (18)0.69087 (6)0.0240 (5)
C50.8254 (3)0.60835 (17)0.73047 (6)0.0224 (5)
H50.95350.62770.74010.027*
C60.6882 (3)0.69845 (18)0.74376 (6)0.0217 (5)
C70.7249 (3)0.70419 (16)0.78349 (5)0.0211 (5)
H70.86280.72500.78560.025*
C80.7082 (3)0.59695 (17)0.80415 (6)0.0209 (5)
C90.8147 (4)0.50465 (17)0.78578 (6)0.0257 (5)
H9A0.95410.51340.78950.031*
H9B0.77570.43530.79610.031*
C100.7762 (4)0.50003 (17)0.74724 (6)0.0260 (5)
H10A0.63960.48290.74320.031*
H10B0.85470.44230.73680.031*
C110.6151 (4)0.79569 (18)0.80144 (6)0.0250 (5)
H11A0.65300.86470.79080.030*
H11B0.47650.78550.79710.030*
C120.6455 (3)0.80507 (17)0.83995 (6)0.0216 (5)
C130.6707 (3)0.70130 (17)0.85983 (5)0.0202 (5)
H130.54090.66720.85940.024*
C140.8015 (3)0.61930 (17)0.84082 (6)0.0209 (5)
C150.8127 (4)0.51426 (17)0.86228 (6)0.0236 (5)
H15A0.68910.47560.86030.028*
H15B0.91360.46740.85260.028*
C160.8564 (4)0.53346 (18)0.90039 (6)0.0246 (5)
H16A0.85450.46360.91260.030*
H16B0.98670.56410.90260.030*
C170.7116 (3)0.61004 (18)0.91721 (6)0.0222 (5)
C180.7123 (3)0.71981 (17)0.89836 (5)0.0204 (5)
H180.60310.76280.90770.025*
C190.8967 (4)0.78302 (18)0.90615 (6)0.0239 (5)
H19A0.88980.85350.89440.029*
H19B1.00700.74320.89650.029*
C200.9346 (4)0.8027 (2)0.94448 (6)0.0275 (5)
C210.9352 (4)0.6923 (2)0.96255 (6)0.0286 (5)
H21A1.04790.65060.95470.034*
H21B0.94850.70370.98750.034*
C220.7538 (4)0.62654 (18)0.95579 (6)0.0262 (5)
H22A0.64330.66350.96650.031*
H22B0.76720.55520.96680.031*
C231.0282 (4)0.52563 (19)0.68376 (6)0.0310 (6)
H23A1.06500.53090.65970.046*
H23B0.98970.45150.68890.046*
H23C1.13740.54570.69820.046*
C240.6862 (4)0.5619 (2)0.67035 (6)0.0311 (6)
H24A0.58300.61530.67150.047*
H24B0.64130.49360.68000.047*
H24C0.72370.55110.64650.047*
C250.4751 (4)0.6817 (2)0.73452 (6)0.0286 (5)
H25A0.44320.60510.73630.043*
H25B0.45220.70650.71110.043*
H25C0.39460.72290.75030.043*
C260.4960 (4)0.56045 (19)0.80771 (6)0.0276 (5)
H26A0.45240.52940.78600.041*
H26B0.41600.62260.81350.041*
H26C0.48600.50620.82580.041*
C271.0085 (3)0.66348 (18)0.83667 (6)0.0232 (5)
H27A1.08570.64230.85650.035*
H27B1.00460.74220.83510.035*
H27C1.06580.63380.81580.035*
C280.5095 (4)0.56109 (18)0.91635 (6)0.0252 (5)
C291.1334 (4)0.8542 (2)0.94813 (7)0.0374 (7)
H29A1.13450.92400.93650.056*
H29B1.23000.80700.93780.056*
H29C1.16260.86460.97240.056*
C300.7847 (4)0.8789 (2)0.96021 (6)0.0360 (6)
H30A0.81410.89020.98440.054*
H30B0.65690.84690.95800.054*
H30C0.78770.94810.94820.054*
C310.3242 (4)0.4050 (2)0.92880 (8)0.0384 (7)
H31A0.26540.39950.90590.046*
H31B0.23780.44750.94370.046*
C320.3546 (4)0.29481 (19)0.94361 (7)0.0304 (6)
C330.3912 (4)0.2077 (2)0.92240 (7)0.0326 (6)
H330.39710.21830.89840.039*
C340.4195 (4)0.1051 (2)0.93572 (7)0.0350 (6)
H340.44490.04610.92100.042*
C350.4104 (4)0.0901 (2)0.97059 (7)0.0383 (7)
H350.43100.02040.97990.046*
C360.3715 (5)0.1755 (2)0.99212 (7)0.0436 (7)
H360.36230.16421.01610.052*
C370.3456 (4)0.2783 (2)0.97862 (7)0.0394 (7)
H370.32180.33730.99350.047*
C381.1264 (4)0.72903 (19)0.63014 (6)0.0276 (5)
C391.1258 (4)0.7154 (2)0.59200 (6)0.0372 (6)
H39A1.23180.75660.58210.056*
H39B1.00400.74160.58270.056*
H39C1.14120.63900.58640.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0211 (9)0.0358 (9)0.0254 (8)0.0005 (7)0.0013 (7)0.0001 (7)
O20.0235 (10)0.0373 (10)0.0396 (10)0.0029 (8)0.0000 (8)0.0018 (8)
O30.0323 (10)0.0215 (7)0.0294 (8)0.0048 (8)0.0013 (8)0.0008 (7)
O40.0194 (9)0.0304 (9)0.0448 (10)0.0015 (8)0.0003 (8)0.0097 (8)
O50.0194 (10)0.0228 (8)0.0519 (11)0.0029 (7)0.0005 (8)0.0109 (8)
C10.0280 (13)0.0216 (11)0.0253 (11)0.0038 (10)0.0015 (10)0.0005 (9)
C20.0298 (14)0.0257 (11)0.0246 (11)0.0007 (11)0.0001 (10)0.0022 (9)
C30.0230 (13)0.0275 (11)0.0222 (11)0.0019 (10)0.0010 (9)0.0012 (9)
C40.0228 (12)0.0238 (10)0.0254 (11)0.0008 (10)0.0001 (10)0.0032 (9)
C50.0221 (13)0.0194 (10)0.0259 (11)0.0016 (10)0.0034 (10)0.0003 (9)
C60.0213 (12)0.0193 (10)0.0246 (11)0.0010 (9)0.0013 (9)0.0008 (9)
C70.0212 (12)0.0160 (9)0.0260 (11)0.0025 (9)0.0020 (9)0.0008 (8)
C80.0189 (12)0.0174 (9)0.0265 (11)0.0015 (9)0.0012 (9)0.0017 (8)
C90.0333 (14)0.0162 (10)0.0278 (12)0.0015 (10)0.0020 (11)0.0004 (9)
C100.0293 (14)0.0193 (10)0.0294 (12)0.0002 (10)0.0007 (11)0.0031 (9)
C110.0245 (13)0.0238 (11)0.0267 (11)0.0047 (10)0.0031 (10)0.0042 (9)
C120.0173 (12)0.0202 (10)0.0273 (11)0.0023 (9)0.0002 (9)0.0036 (9)
C130.0183 (12)0.0187 (9)0.0237 (10)0.0007 (9)0.0012 (9)0.0019 (8)
C140.0186 (12)0.0182 (10)0.0259 (11)0.0001 (9)0.0015 (9)0.0017 (8)
C150.0228 (13)0.0197 (10)0.0283 (12)0.0028 (9)0.0005 (10)0.0030 (9)
C160.0219 (13)0.0234 (11)0.0285 (12)0.0022 (10)0.0002 (10)0.0056 (9)
C170.0182 (12)0.0210 (10)0.0276 (11)0.0015 (9)0.0017 (9)0.0033 (9)
C180.0194 (12)0.0182 (10)0.0237 (10)0.0016 (9)0.0004 (9)0.0021 (8)
C190.0244 (13)0.0226 (11)0.0248 (11)0.0009 (10)0.0001 (10)0.0024 (9)
C200.0267 (14)0.0311 (12)0.0246 (11)0.0018 (11)0.0016 (10)0.0011 (10)
C210.0277 (14)0.0337 (13)0.0245 (11)0.0022 (11)0.0042 (10)0.0027 (10)
C220.0279 (14)0.0265 (11)0.0241 (11)0.0008 (10)0.0005 (10)0.0061 (9)
C230.0331 (15)0.0277 (12)0.0321 (13)0.0029 (11)0.0023 (11)0.0036 (10)
C240.0301 (15)0.0324 (12)0.0308 (13)0.0079 (11)0.0045 (11)0.0049 (10)
C250.0240 (13)0.0334 (12)0.0283 (12)0.0022 (11)0.0040 (10)0.0003 (10)
C260.0216 (13)0.0292 (12)0.0320 (12)0.0039 (11)0.0038 (11)0.0020 (10)
C270.0180 (12)0.0249 (10)0.0267 (11)0.0007 (10)0.0002 (10)0.0017 (9)
C280.0242 (14)0.0247 (11)0.0269 (12)0.0003 (10)0.0002 (10)0.0026 (9)
C290.0408 (17)0.0415 (14)0.0300 (13)0.0147 (13)0.0062 (13)0.0002 (11)
C300.0464 (18)0.0291 (12)0.0324 (13)0.0015 (13)0.0032 (13)0.0028 (10)
C310.0182 (14)0.0337 (13)0.0634 (18)0.0061 (12)0.0007 (13)0.0156 (13)
C320.0164 (13)0.0277 (12)0.0471 (14)0.0044 (11)0.0001 (11)0.0088 (11)
C330.0228 (14)0.0357 (13)0.0394 (14)0.0028 (11)0.0000 (11)0.0079 (12)
C340.0292 (15)0.0295 (12)0.0462 (15)0.0054 (12)0.0002 (12)0.0010 (11)
C350.0344 (17)0.0305 (13)0.0500 (17)0.0054 (12)0.0004 (13)0.0100 (12)
C360.052 (2)0.0412 (15)0.0375 (14)0.0041 (15)0.0039 (14)0.0095 (12)
C370.0404 (18)0.0333 (13)0.0447 (15)0.0041 (13)0.0060 (13)0.0006 (12)
C380.0220 (13)0.0239 (11)0.0370 (13)0.0023 (10)0.0025 (11)0.0024 (10)
C390.0291 (15)0.0497 (16)0.0329 (13)0.0043 (13)0.0057 (12)0.0002 (12)
Geometric parameters (Å, º) top
O1—C381.357 (3)C18—C191.538 (3)
O1—C31.463 (3)C18—H181.0000
O2—C381.210 (3)C19—C201.543 (3)
O3—C121.218 (3)C19—H19A0.9900
O4—C281.208 (3)C19—H19B0.9900
O5—C281.353 (3)C20—C291.535 (4)
O5—C311.465 (3)C20—C301.539 (4)
C1—C21.537 (3)C20—C211.543 (3)
C1—C61.546 (3)C21—C221.529 (3)
C1—H1A0.9900C21—H21A0.9900
C1—H1B0.9900C21—H21B0.9900
C2—C31.514 (3)C22—H22A0.9900
C2—H2A0.9900C22—H22B0.9900
C2—H2B0.9900C23—H23A0.9800
C3—C41.540 (3)C23—H23B0.9800
C3—H31.0000C23—H23C0.9800
C4—C241.536 (3)C24—H24A0.9800
C4—C231.540 (3)C24—H24B0.9800
C4—C51.570 (3)C24—H24C0.9800
C5—C101.536 (3)C25—H25A0.9800
C5—C61.562 (3)C25—H25B0.9800
C5—H51.0000C25—H25C0.9800
C6—C251.545 (3)C26—H26A0.9800
C6—C71.578 (3)C26—H26B0.9800
C7—C111.540 (3)C26—H26C0.9800
C7—C81.563 (3)C27—H27A0.9800
C7—H71.0000C27—H27B0.9800
C8—C91.544 (3)C27—H27C0.9800
C8—C261.554 (3)C29—H29A0.9800
C8—C141.601 (3)C29—H29B0.9800
C9—C101.533 (3)C29—H29C0.9800
C9—H9A0.9900C30—H30A0.9800
C9—H9B0.9900C30—H30B0.9800
C10—H10A0.9900C30—H30C0.9800
C10—H10B0.9900C31—C321.502 (3)
C11—C121.527 (3)C31—H31A0.9900
C11—H11A0.9900C31—H31B0.9900
C11—H11B0.9900C32—C371.387 (4)
C12—C131.516 (3)C32—C331.388 (4)
C13—C181.553 (3)C33—C341.391 (4)
C13—C141.557 (3)C33—H330.9500
C13—H131.0000C34—C351.379 (4)
C14—C271.554 (3)C34—H340.9500
C14—C151.554 (3)C35—C361.382 (4)
C15—C161.542 (3)C35—H350.9500
C15—H15A0.9900C36—C371.394 (4)
C15—H15B0.9900C36—H360.9500
C16—C171.536 (3)C37—H370.9500
C16—H16A0.9900C38—C391.503 (3)
C16—H16B0.9900C39—H39A0.9800
C17—C281.535 (3)C39—H39B0.9800
C17—C181.551 (3)C39—H39C0.9800
C17—C221.552 (3)
C38—O1—C3118.35 (19)C17—C18—H18107.0
C28—O5—C31115.34 (19)C13—C18—H18107.0
C2—C1—C6113.16 (18)C18—C19—C20114.63 (19)
C2—C1—H1A108.9C18—C19—H19A108.6
C6—C1—H1A108.9C20—C19—H19A108.6
C2—C1—H1B108.9C18—C19—H19B108.6
C6—C1—H1B108.9C20—C19—H19B108.6
H1A—C1—H1B107.8H19A—C19—H19B107.6
C3—C2—C1109.71 (19)C29—C20—C30108.7 (2)
C3—C2—H2A109.7C29—C20—C19108.1 (2)
C1—C2—H2A109.7C30—C20—C19111.7 (2)
C3—C2—H2B109.7C29—C20—C21109.0 (2)
C1—C2—H2B109.7C30—C20—C21111.4 (2)
H2A—C2—H2B108.2C19—C20—C21107.8 (2)
O1—C3—C2107.98 (18)C22—C21—C20113.1 (2)
O1—C3—C4108.78 (18)C22—C21—H21A109.0
C2—C3—C4113.5 (2)C20—C21—H21A109.0
O1—C3—H3108.8C22—C21—H21B109.0
C2—C3—H3108.8C20—C21—H21B109.0
C4—C3—H3108.8H21A—C21—H21B107.8
C24—C4—C23107.83 (19)C21—C22—C17113.34 (19)
C24—C4—C3112.1 (2)C21—C22—H22A108.9
C23—C4—C3107.6 (2)C17—C22—H22A108.9
C24—C4—C5114.4 (2)C21—C22—H22B108.9
C23—C4—C5108.91 (19)C17—C22—H22B108.9
C3—C4—C5105.82 (17)H22A—C22—H22B107.7
C10—C5—C6110.40 (19)C4—C23—H23A109.5
C10—C5—C4114.42 (18)C4—C23—H23B109.5
C6—C5—C4117.15 (18)H23A—C23—H23B109.5
C10—C5—H5104.4C4—C23—H23C109.5
C6—C5—H5104.4H23A—C23—H23C109.5
C4—C5—H5104.4H23B—C23—H23C109.5
C25—C6—C1108.03 (19)C4—C24—H24A109.5
C25—C6—C5114.53 (19)C4—C24—H24B109.5
C1—C6—C5108.23 (19)H24A—C24—H24B109.5
C25—C6—C7113.15 (19)C4—C24—H24C109.5
C1—C6—C7107.43 (17)H24A—C24—H24C109.5
C5—C6—C7105.16 (17)H24B—C24—H24C109.5
C11—C7—C8110.84 (18)C6—C25—H25A109.5
C11—C7—C6113.74 (18)C6—C25—H25B109.5
C8—C7—C6117.36 (17)H25A—C25—H25B109.5
C11—C7—H7104.5C6—C25—H25C109.5
C8—C7—H7104.5H25A—C25—H25C109.5
C6—C7—H7104.5H25B—C25—H25C109.5
C9—C8—C26106.47 (19)C8—C26—H26A109.5
C9—C8—C7110.85 (18)C8—C26—H26B109.5
C26—C8—C7111.48 (19)H26A—C26—H26B109.5
C9—C8—C14110.53 (18)C8—C26—H26C109.5
C26—C8—C14110.96 (19)H26A—C26—H26C109.5
C7—C8—C14106.62 (17)H26B—C26—H26C109.5
C10—C9—C8113.69 (19)C14—C27—H27A109.5
C10—C9—H9A108.8C14—C27—H27B109.5
C8—C9—H9A108.8H27A—C27—H27B109.5
C10—C9—H9B108.8C14—C27—H27C109.5
C8—C9—H9B108.8H27A—C27—H27C109.5
H9A—C9—H9B107.7H27B—C27—H27C109.5
C9—C10—C5110.40 (18)O4—C28—O5122.3 (2)
C9—C10—H10A109.6O4—C28—C17126.5 (2)
C5—C10—H10A109.6O5—C28—C17111.1 (2)
C9—C10—H10B109.6C20—C29—H29A109.5
C5—C10—H10B109.6C20—C29—H29B109.5
H10A—C10—H10B108.1H29A—C29—H29B109.5
C12—C11—C7115.97 (18)C20—C29—H29C109.5
C12—C11—H11A108.3H29A—C29—H29C109.5
C7—C11—H11A108.3H29B—C29—H29C109.5
C12—C11—H11B108.3C20—C30—H30A109.5
C7—C11—H11B108.3C20—C30—H30B109.5
H11A—C11—H11B107.4H30A—C30—H30B109.5
O3—C12—C13122.5 (2)C20—C30—H30C109.5
O3—C12—C11120.04 (19)H30A—C30—H30C109.5
C13—C12—C11117.27 (19)H30B—C30—H30C109.5
C12—C13—C18113.23 (17)O5—C31—C32107.4 (2)
C12—C13—C14112.28 (18)O5—C31—H31A110.2
C18—C13—C14116.85 (18)C32—C31—H31A110.2
C12—C13—H13104.3O5—C31—H31B110.2
C18—C13—H13104.3C32—C31—H31B110.2
C14—C13—H13104.3H31A—C31—H31B108.5
C27—C14—C15107.85 (18)C37—C32—C33119.0 (2)
C27—C14—C13111.32 (18)C37—C32—C31120.7 (3)
C15—C14—C13108.69 (18)C33—C32—C31120.4 (2)
C27—C14—C8110.22 (18)C32—C33—C34121.1 (2)
C15—C14—C8111.08 (17)C32—C33—H33119.5
C13—C14—C8107.69 (18)C34—C33—H33119.5
C16—C15—C14113.79 (18)C35—C34—C33119.2 (3)
C16—C15—H15A108.8C35—C34—H34120.4
C14—C15—H15A108.8C33—C34—H34120.4
C16—C15—H15B108.8C34—C35—C36120.6 (3)
C14—C15—H15B108.8C34—C35—H35119.7
H15A—C15—H15B107.7C36—C35—H35119.7
C17—C16—C15112.36 (19)C35—C36—C37119.8 (3)
C17—C16—H16A109.1C35—C36—H36120.1
C15—C16—H16A109.1C37—C36—H36120.1
C17—C16—H16B109.1C32—C37—C36120.3 (3)
C15—C16—H16B109.1C32—C37—H37119.8
H16A—C16—H16B107.9C36—C37—H37119.8
C28—C17—C16110.44 (19)O2—C38—O1124.5 (2)
C28—C17—C18109.94 (18)O2—C38—C39125.1 (2)
C16—C17—C18109.78 (18)O1—C38—C39110.4 (2)
C28—C17—C22104.36 (19)C38—C39—H39A109.5
C16—C17—C22111.95 (19)C38—C39—H39B109.5
C18—C17—C22110.26 (18)H39A—C39—H39B109.5
C19—C18—C17110.94 (18)C38—C39—H39C109.5
C19—C18—C13115.12 (18)H39A—C39—H39C109.5
C17—C18—C13109.36 (17)H39B—C39—H39C109.5
C19—C18—H18107.0
C6—C1—C2—C357.7 (3)C26—C8—C14—C27175.96 (17)
C38—O1—C3—C2124.9 (2)C7—C8—C14—C2754.4 (2)
C38—O1—C3—C4111.5 (2)C9—C8—C14—C1553.3 (2)
C1—C2—C3—O1177.77 (19)C26—C8—C14—C1564.6 (2)
C1—C2—C3—C461.5 (3)C7—C8—C14—C15173.87 (19)
O1—C3—C4—C2451.8 (3)C9—C8—C14—C13172.22 (18)
C2—C3—C4—C2468.4 (3)C26—C8—C14—C1354.3 (2)
O1—C3—C4—C2366.5 (2)C7—C8—C14—C1367.2 (2)
C2—C3—C4—C23173.21 (19)C27—C14—C15—C1672.6 (2)
O1—C3—C4—C5177.16 (18)C13—C14—C15—C1648.2 (3)
C2—C3—C4—C556.9 (2)C8—C14—C15—C16166.6 (2)
C24—C4—C5—C1060.5 (3)C14—C15—C16—C1755.9 (3)
C23—C4—C5—C1060.3 (3)C15—C16—C17—C2862.7 (2)
C3—C4—C5—C10175.7 (2)C15—C16—C17—C1858.7 (3)
C24—C4—C5—C671.1 (3)C15—C16—C17—C22178.55 (19)
C23—C4—C5—C6168.2 (2)C28—C17—C18—C19166.22 (19)
C3—C4—C5—C652.8 (3)C16—C17—C18—C1972.1 (2)
C2—C1—C6—C2573.3 (2)C22—C17—C18—C1951.7 (3)
C2—C1—C6—C551.3 (3)C28—C17—C18—C1365.7 (2)
C2—C1—C6—C7164.3 (2)C16—C17—C18—C1355.9 (3)
C10—C5—C6—C2563.7 (2)C22—C17—C18—C13179.73 (19)
C4—C5—C6—C2569.6 (3)C12—C13—C18—C1961.1 (3)
C10—C5—C6—C1175.72 (18)C14—C13—C18—C1971.7 (2)
C4—C5—C6—C150.9 (3)C12—C13—C18—C17173.25 (19)
C10—C5—C6—C761.1 (2)C14—C13—C18—C1753.9 (3)
C4—C5—C6—C7165.52 (19)C17—C18—C19—C2056.2 (3)
C25—C6—C7—C1159.2 (3)C13—C18—C19—C20178.95 (19)
C1—C6—C7—C1159.9 (3)C18—C19—C20—C29173.4 (2)
C5—C6—C7—C11175.05 (19)C18—C19—C20—C3067.1 (3)
C25—C6—C7—C872.5 (3)C18—C19—C20—C2155.7 (3)
C1—C6—C7—C8168.4 (2)C29—C20—C21—C22171.2 (2)
C5—C6—C7—C853.3 (3)C30—C20—C21—C2268.9 (3)
C11—C7—C8—C9178.83 (19)C19—C20—C21—C2254.0 (3)
C6—C7—C8—C945.8 (3)C20—C21—C22—C1754.9 (3)
C11—C7—C8—C2660.4 (2)C28—C17—C22—C21170.27 (19)
C6—C7—C8—C2672.6 (3)C16—C17—C22—C2170.3 (2)
C11—C7—C8—C1460.8 (2)C18—C17—C22—C2152.3 (3)
C6—C7—C8—C14166.19 (19)C31—O5—C28—O40.4 (4)
C26—C8—C9—C1076.6 (2)C31—O5—C28—C17176.0 (2)
C7—C8—C9—C1044.8 (3)C16—C17—C28—O4137.1 (2)
C14—C8—C9—C10162.80 (19)C18—C17—C28—O415.8 (3)
C8—C9—C10—C555.7 (3)C22—C17—C28—O4102.4 (3)
C6—C5—C10—C965.2 (3)C16—C17—C28—O546.6 (3)
C4—C5—C10—C9160.1 (2)C18—C17—C28—O5167.90 (18)
C8—C7—C11—C1245.3 (3)C22—C17—C28—O573.9 (2)
C6—C7—C11—C12179.96 (19)C28—O5—C31—C32174.5 (2)
C7—C11—C12—O3149.9 (2)O5—C31—C32—C3791.0 (3)
C7—C11—C12—C1335.4 (3)O5—C31—C32—C3389.4 (3)
O3—C12—C13—C188.7 (3)C37—C32—C33—C340.2 (4)
C11—C12—C13—C18176.7 (2)C31—C32—C33—C34179.9 (3)
O3—C12—C13—C14143.7 (2)C32—C33—C34—C350.2 (4)
C11—C12—C13—C1441.7 (3)C33—C34—C35—C360.7 (5)
C12—C13—C14—C2763.6 (2)C34—C35—C36—C371.5 (5)
C18—C13—C14—C2769.7 (2)C33—C32—C37—C360.5 (4)
C12—C13—C14—C15177.79 (19)C31—C32—C37—C36179.1 (3)
C18—C13—C14—C1549.0 (3)C35—C36—C37—C321.4 (5)
C12—C13—C14—C857.4 (2)C3—O1—C38—O26.1 (3)
C18—C13—C14—C8169.39 (18)C3—O1—C38—C39173.1 (2)
C9—C8—C14—C2766.2 (2)

Experimental details

Crystal data
Chemical formulaC39H56O5
Mr604.84
Crystal system, space groupOrthorhombic, P212121
Temperature (K)113
a, b, c (Å)6.9775 (3), 12.4235 (5), 39.1480 (16)
V3)3393.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.16 × 0.14 × 0.12
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
CrystalClear
Tmin, Tmax0.980, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
31130, 4606, 4201
Rint0.061
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.114, 1.09
No. of reflections4606
No. of parameters406
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.18

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This project was supported financially by the Higher Education Department of Liaoning Province Research Foundation (grant LS2020089), the Graduate Education Innovation Program 2010 and the Science and Technology Department of Liaoning Province Science Foundation (grant 2010226003).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationHonda, Y., Honda, T., Roy, S. & Gribble, G. W. (2003). J. Org. Chem. 68, 4991–4993.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLiu, J. (1995). J. Ethnopharmacol. 49, 57–68.  CrossRef CAS PubMed Web of Science Google Scholar
First citationMatsuda, H., Li, Y. H., Murakami, T., Yamahara, J. & Yoshikawa, M. (1999). Bioorg. Med. Chem. 7, 323–327.  Web of Science CrossRef PubMed CAS Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, H.-X., Ye, Y.-P., Wang, K.-W. & Pan, Y.-J. (2003). Acta Cryst. E59, o989–o991.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1027
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