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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Apr 7;67(Pt 5):o1027. doi: 10.1107/S1600536811010968

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

Jun-yi Hu a,*, Ying-qian Xu a, Guo-bo Xu b, Kang Wang a, Peng Lei a
PMCID: PMC3089225  PMID: 21754358

Abstract

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 ▶); Liu (1995 ▶); Matsuda et al. (1999 ▶); Sun et al. (2003 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). graphic file with name e-67-o1027-scheme1.jpg

Experimental

Crystal data

  • C39H56O5

  • M r = 604.84

  • Orthorhombic, Inline graphic

  • 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 ▶)T min = 0.980, T max = 0.991

  • 31130 measured reflections

  • 4606 independent reflections

  • 4201 reflections with I > 2σ(I)

  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050

  • wR(F 2) = 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 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010968/yk2003sup1.cif

e-67-o1027-sup1.cif (32.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010968/yk2003Isup2.hkl

e-67-o1027-Isup2.hkl (225.7KB, hkl)

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.

Fig. 1.

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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.

Crystal data

C39H56O5 F(000) = 1320
Mr = 604.84 Dx = 1.184 Mg m−3
Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 6474 reflections
a = 6.9775 (3) Å θ = 1.7–27.9°
b = 12.4235 (5) Å µ = 0.08 mm−1
c = 39.1480 (16) Å T = 113 K
V = 3393.5 (2) Å3 Block, colourless
Z = 4 0.16 × 0.14 × 0.12 mm
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Data collection

Rigaku Saturn diffractometer 4606 independent reflections
Radiation source: rotating anode 4201 reflections with I > 2σ(I)
confocal Rint = 0.061
Detector resolution: 7.31 pixels mm-1 θmax = 27.9°, θmin = 1.7°
ω scans h = −8→9
Absorption correction: multi-scan CrystalClear k = −16→16
Tmin = 0.980, Tmax = 0.991 l = −48→51
31130 measured reflections
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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)] = 0.050 H-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 reflections Δρmax = 0.24 e Å−3
406 parameters Δρmin = −0.18 e Å−3
0 restraints Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods Extinction coefficient: 0.0053 (7)
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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
O1 0.9465 (2) 0.71768 (14) 0.64283 (4) 0.0274 (4)
O2 1.2672 (3) 0.74643 (14) 0.64732 (5) 0.0335 (4)
O3 0.6349 (3) 0.89260 (13) 0.85384 (4) 0.0277 (4)
O4 0.3626 (3) 0.60770 (14) 0.90948 (5) 0.0315 (4)
O5 0.5121 (3) 0.45703 (13) 0.92650 (5) 0.0314 (4)
C1 0.7536 (4) 0.80684 (18) 0.72827 (6) 0.0250 (5)
H1A 0.6580 0.8629 0.7340 0.030*
H1B 0.8770 0.8280 0.7388 0.030*
C2 0.7781 (4) 0.80269 (19) 0.68926 (6) 0.0267 (5)
H2A 0.6533 0.7870 0.6783 0.032*
H2B 0.8236 0.8733 0.6808 0.032*
C3 0.9216 (4) 0.71608 (18) 0.67993 (5) 0.0242 (5)
H3 1.0471 0.7333 0.6910 0.029*
C4 0.8594 (4) 0.60222 (18) 0.69087 (6) 0.0240 (5)
C5 0.8254 (3) 0.60835 (17) 0.73047 (6) 0.0224 (5)
H5 0.9535 0.6277 0.7401 0.027*
C6 0.6882 (3) 0.69845 (18) 0.74376 (6) 0.0217 (5)
C7 0.7249 (3) 0.70419 (16) 0.78349 (5) 0.0211 (5)
H7 0.8628 0.7250 0.7856 0.025*
C8 0.7082 (3) 0.59695 (17) 0.80415 (6) 0.0209 (5)
C9 0.8147 (4) 0.50465 (17) 0.78578 (6) 0.0257 (5)
H9A 0.9541 0.5134 0.7895 0.031*
H9B 0.7757 0.4353 0.7961 0.031*
C10 0.7762 (4) 0.50003 (17) 0.74724 (6) 0.0260 (5)
H10A 0.6396 0.4829 0.7432 0.031*
H10B 0.8547 0.4423 0.7368 0.031*
C11 0.6151 (4) 0.79569 (18) 0.80144 (6) 0.0250 (5)
H11A 0.6530 0.8647 0.7908 0.030*
H11B 0.4765 0.7855 0.7971 0.030*
C12 0.6455 (3) 0.80507 (17) 0.83995 (6) 0.0216 (5)
C13 0.6707 (3) 0.70130 (17) 0.85983 (5) 0.0202 (5)
H13 0.5409 0.6672 0.8594 0.024*
C14 0.8015 (3) 0.61930 (17) 0.84082 (6) 0.0209 (5)
C15 0.8127 (4) 0.51426 (17) 0.86228 (6) 0.0236 (5)
H15A 0.6891 0.4756 0.8603 0.028*
H15B 0.9136 0.4674 0.8526 0.028*
C16 0.8564 (4) 0.53346 (18) 0.90039 (6) 0.0246 (5)
H16A 0.8545 0.4636 0.9126 0.030*
H16B 0.9867 0.5641 0.9026 0.030*
C17 0.7116 (3) 0.61004 (18) 0.91721 (6) 0.0222 (5)
C18 0.7123 (3) 0.71981 (17) 0.89836 (5) 0.0204 (5)
H18 0.6031 0.7628 0.9077 0.025*
C19 0.8967 (4) 0.78302 (18) 0.90615 (6) 0.0239 (5)
H19A 0.8898 0.8535 0.8944 0.029*
H19B 1.0070 0.7432 0.8965 0.029*
C20 0.9346 (4) 0.8027 (2) 0.94448 (6) 0.0275 (5)
C21 0.9352 (4) 0.6923 (2) 0.96255 (6) 0.0286 (5)
H21A 1.0479 0.6506 0.9547 0.034*
H21B 0.9485 0.7037 0.9875 0.034*
C22 0.7538 (4) 0.62654 (18) 0.95579 (6) 0.0262 (5)
H22A 0.6433 0.6635 0.9665 0.031*
H22B 0.7672 0.5552 0.9668 0.031*
C23 1.0282 (4) 0.52563 (19) 0.68376 (6) 0.0310 (6)
H23A 1.0650 0.5309 0.6597 0.046*
H23B 0.9897 0.4515 0.6889 0.046*
H23C 1.1374 0.5457 0.6982 0.046*
C24 0.6862 (4) 0.5619 (2) 0.67035 (6) 0.0311 (6)
H24A 0.5830 0.6153 0.6715 0.047*
H24B 0.6413 0.4936 0.6800 0.047*
H24C 0.7237 0.5511 0.6465 0.047*
C25 0.4751 (4) 0.6817 (2) 0.73452 (6) 0.0286 (5)
H25A 0.4432 0.6051 0.7363 0.043*
H25B 0.4522 0.7065 0.7111 0.043*
H25C 0.3946 0.7229 0.7503 0.043*
C26 0.4960 (4) 0.56045 (19) 0.80771 (6) 0.0276 (5)
H26A 0.4524 0.5294 0.7860 0.041*
H26B 0.4160 0.6226 0.8135 0.041*
H26C 0.4860 0.5062 0.8258 0.041*
C27 1.0085 (3) 0.66348 (18) 0.83667 (6) 0.0232 (5)
H27A 1.0857 0.6423 0.8565 0.035*
H27B 1.0046 0.7422 0.8351 0.035*
H27C 1.0658 0.6338 0.8158 0.035*
C28 0.5095 (4) 0.56109 (18) 0.91635 (6) 0.0252 (5)
C29 1.1334 (4) 0.8542 (2) 0.94813 (7) 0.0374 (7)
H29A 1.1345 0.9240 0.9365 0.056*
H29B 1.2300 0.8070 0.9378 0.056*
H29C 1.1626 0.8646 0.9724 0.056*
C30 0.7847 (4) 0.8789 (2) 0.96021 (6) 0.0360 (6)
H30A 0.8141 0.8902 0.9844 0.054*
H30B 0.6569 0.8469 0.9580 0.054*
H30C 0.7877 0.9481 0.9482 0.054*
C31 0.3242 (4) 0.4050 (2) 0.92880 (8) 0.0384 (7)
H31A 0.2654 0.3995 0.9059 0.046*
H31B 0.2378 0.4475 0.9437 0.046*
C32 0.3546 (4) 0.29481 (19) 0.94361 (7) 0.0304 (6)
C33 0.3912 (4) 0.2077 (2) 0.92240 (7) 0.0326 (6)
H33 0.3971 0.2183 0.8984 0.039*
C34 0.4195 (4) 0.1051 (2) 0.93572 (7) 0.0350 (6)
H34 0.4449 0.0461 0.9210 0.042*
C35 0.4104 (4) 0.0901 (2) 0.97059 (7) 0.0383 (7)
H35 0.4310 0.0204 0.9799 0.046*
C36 0.3715 (5) 0.1755 (2) 0.99212 (7) 0.0436 (7)
H36 0.3623 0.1642 1.0161 0.052*
C37 0.3456 (4) 0.2783 (2) 0.97862 (7) 0.0394 (7)
H37 0.3218 0.3373 0.9935 0.047*
C38 1.1264 (4) 0.72903 (19) 0.63014 (6) 0.0276 (5)
C39 1.1258 (4) 0.7154 (2) 0.59200 (6) 0.0372 (6)
H39A 1.2318 0.7566 0.5821 0.056*
H39B 1.0040 0.7416 0.5827 0.056*
H39C 1.1412 0.6390 0.5864 0.056*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0211 (9) 0.0358 (9) 0.0254 (8) −0.0005 (7) 0.0013 (7) −0.0001 (7)
O2 0.0235 (10) 0.0373 (10) 0.0396 (10) −0.0029 (8) 0.0000 (8) 0.0018 (8)
O3 0.0323 (10) 0.0215 (7) 0.0294 (8) 0.0048 (8) −0.0013 (8) 0.0008 (7)
O4 0.0194 (9) 0.0304 (9) 0.0448 (10) 0.0015 (8) 0.0003 (8) 0.0097 (8)
O5 0.0194 (10) 0.0228 (8) 0.0519 (11) −0.0029 (7) −0.0005 (8) 0.0109 (8)
C1 0.0280 (13) 0.0216 (11) 0.0253 (11) 0.0038 (10) −0.0015 (10) 0.0005 (9)
C2 0.0298 (14) 0.0257 (11) 0.0246 (11) 0.0007 (11) −0.0001 (10) 0.0022 (9)
C3 0.0230 (13) 0.0275 (11) 0.0222 (11) −0.0019 (10) −0.0010 (9) −0.0012 (9)
C4 0.0228 (12) 0.0238 (10) 0.0254 (11) −0.0008 (10) −0.0001 (10) −0.0032 (9)
C5 0.0221 (13) 0.0194 (10) 0.0259 (11) 0.0016 (10) −0.0034 (10) −0.0003 (9)
C6 0.0213 (12) 0.0193 (10) 0.0246 (11) 0.0010 (9) −0.0013 (9) 0.0008 (9)
C7 0.0212 (12) 0.0160 (9) 0.0260 (11) 0.0025 (9) −0.0020 (9) 0.0008 (8)
C8 0.0189 (12) 0.0174 (9) 0.0265 (11) −0.0015 (9) −0.0012 (9) 0.0017 (8)
C9 0.0333 (14) 0.0162 (10) 0.0278 (12) 0.0015 (10) −0.0020 (11) −0.0004 (9)
C10 0.0293 (14) 0.0193 (10) 0.0294 (12) −0.0002 (10) −0.0007 (11) −0.0031 (9)
C11 0.0245 (13) 0.0238 (11) 0.0267 (11) 0.0047 (10) −0.0031 (10) 0.0042 (9)
C12 0.0173 (12) 0.0202 (10) 0.0273 (11) 0.0023 (9) 0.0002 (9) 0.0036 (9)
C13 0.0183 (12) 0.0187 (9) 0.0237 (10) 0.0007 (9) −0.0012 (9) 0.0019 (8)
C14 0.0186 (12) 0.0182 (10) 0.0259 (11) −0.0001 (9) −0.0015 (9) 0.0017 (8)
C15 0.0228 (13) 0.0197 (10) 0.0283 (12) 0.0028 (9) 0.0005 (10) 0.0030 (9)
C16 0.0219 (13) 0.0234 (11) 0.0285 (12) 0.0022 (10) −0.0002 (10) 0.0056 (9)
C17 0.0182 (12) 0.0210 (10) 0.0276 (11) −0.0015 (9) −0.0017 (9) 0.0033 (9)
C18 0.0194 (12) 0.0182 (10) 0.0237 (10) 0.0016 (9) 0.0004 (9) 0.0021 (8)
C19 0.0244 (13) 0.0226 (11) 0.0248 (11) −0.0009 (10) −0.0001 (10) 0.0024 (9)
C20 0.0267 (14) 0.0311 (12) 0.0246 (11) −0.0018 (11) −0.0016 (10) 0.0011 (10)
C21 0.0277 (14) 0.0337 (13) 0.0245 (11) −0.0022 (11) −0.0042 (10) 0.0027 (10)
C22 0.0279 (14) 0.0265 (11) 0.0241 (11) −0.0008 (10) −0.0005 (10) 0.0061 (9)
C23 0.0331 (15) 0.0277 (12) 0.0321 (13) 0.0029 (11) 0.0023 (11) −0.0036 (10)
C24 0.0301 (15) 0.0324 (12) 0.0308 (13) −0.0079 (11) −0.0045 (11) −0.0049 (10)
C25 0.0240 (13) 0.0334 (12) 0.0283 (12) 0.0022 (11) −0.0040 (10) 0.0003 (10)
C26 0.0216 (13) 0.0292 (12) 0.0320 (12) −0.0039 (11) −0.0038 (11) 0.0020 (10)
C27 0.0180 (12) 0.0249 (10) 0.0267 (11) 0.0007 (10) 0.0002 (10) 0.0017 (9)
C28 0.0242 (14) 0.0247 (11) 0.0269 (12) −0.0003 (10) 0.0002 (10) 0.0026 (9)
C29 0.0408 (17) 0.0415 (14) 0.0300 (13) −0.0147 (13) −0.0062 (13) 0.0002 (11)
C30 0.0464 (18) 0.0291 (12) 0.0324 (13) −0.0015 (13) 0.0032 (13) −0.0028 (10)
C31 0.0182 (14) 0.0337 (13) 0.0634 (18) −0.0061 (12) −0.0007 (13) 0.0156 (13)
C32 0.0164 (13) 0.0277 (12) 0.0471 (14) −0.0044 (11) −0.0001 (11) 0.0088 (11)
C33 0.0228 (14) 0.0357 (13) 0.0394 (14) −0.0028 (11) 0.0000 (11) 0.0079 (12)
C34 0.0292 (15) 0.0295 (12) 0.0462 (15) −0.0054 (12) −0.0002 (12) −0.0010 (11)
C35 0.0344 (17) 0.0305 (13) 0.0500 (17) −0.0054 (12) −0.0004 (13) 0.0100 (12)
C36 0.052 (2) 0.0412 (15) 0.0375 (14) −0.0041 (15) 0.0039 (14) 0.0095 (12)
C37 0.0404 (18) 0.0333 (13) 0.0447 (15) −0.0041 (13) 0.0060 (13) 0.0006 (12)
C38 0.0220 (13) 0.0239 (11) 0.0370 (13) 0.0023 (10) 0.0025 (11) 0.0024 (10)
C39 0.0291 (15) 0.0497 (16) 0.0329 (13) 0.0043 (13) 0.0057 (12) 0.0002 (12)
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Geometric parameters (Å, °)

O1—C38 1.357 (3) C18—C19 1.538 (3)
O1—C3 1.463 (3) C18—H18 1.0000
O2—C38 1.210 (3) C19—C20 1.543 (3)
O3—C12 1.218 (3) C19—H19A 0.9900
O4—C28 1.208 (3) C19—H19B 0.9900
O5—C28 1.353 (3) C20—C29 1.535 (4)
O5—C31 1.465 (3) C20—C30 1.539 (4)
C1—C2 1.537 (3) C20—C21 1.543 (3)
C1—C6 1.546 (3) C21—C22 1.529 (3)
C1—H1A 0.9900 C21—H21A 0.9900
C1—H1B 0.9900 C21—H21B 0.9900
C2—C3 1.514 (3) C22—H22A 0.9900
C2—H2A 0.9900 C22—H22B 0.9900
C2—H2B 0.9900 C23—H23A 0.9800
C3—C4 1.540 (3) C23—H23B 0.9800
C3—H3 1.0000 C23—H23C 0.9800
C4—C24 1.536 (3) C24—H24A 0.9800
C4—C23 1.540 (3) C24—H24B 0.9800
C4—C5 1.570 (3) C24—H24C 0.9800
C5—C10 1.536 (3) C25—H25A 0.9800
C5—C6 1.562 (3) C25—H25B 0.9800
C5—H5 1.0000 C25—H25C 0.9800
C6—C25 1.545 (3) C26—H26A 0.9800
C6—C7 1.578 (3) C26—H26B 0.9800
C7—C11 1.540 (3) C26—H26C 0.9800
C7—C8 1.563 (3) C27—H27A 0.9800
C7—H7 1.0000 C27—H27B 0.9800
C8—C9 1.544 (3) C27—H27C 0.9800
C8—C26 1.554 (3) C29—H29A 0.9800
C8—C14 1.601 (3) C29—H29B 0.9800
C9—C10 1.533 (3) C29—H29C 0.9800
C9—H9A 0.9900 C30—H30A 0.9800
C9—H9B 0.9900 C30—H30B 0.9800
C10—H10A 0.9900 C30—H30C 0.9800
C10—H10B 0.9900 C31—C32 1.502 (3)
C11—C12 1.527 (3) C31—H31A 0.9900
C11—H11A 0.9900 C31—H31B 0.9900
C11—H11B 0.9900 C32—C37 1.387 (4)
C12—C13 1.516 (3) C32—C33 1.388 (4)
C13—C18 1.553 (3) C33—C34 1.391 (4)
C13—C14 1.557 (3) C33—H33 0.9500
C13—H13 1.0000 C34—C35 1.379 (4)
C14—C27 1.554 (3) C34—H34 0.9500
C14—C15 1.554 (3) C35—C36 1.382 (4)
C15—C16 1.542 (3) C35—H35 0.9500
C15—H15A 0.9900 C36—C37 1.394 (4)
C15—H15B 0.9900 C36—H36 0.9500
C16—C17 1.536 (3) C37—H37 0.9500
C16—H16A 0.9900 C38—C39 1.503 (3)
C16—H16B 0.9900 C39—H39A 0.9800
C17—C28 1.535 (3) C39—H39B 0.9800
C17—C18 1.551 (3) C39—H39C 0.9800
C17—C22 1.552 (3)
C38—O1—C3 118.35 (19) C17—C18—H18 107.0
C28—O5—C31 115.34 (19) C13—C18—H18 107.0
C2—C1—C6 113.16 (18) C18—C19—C20 114.63 (19)
C2—C1—H1A 108.9 C18—C19—H19A 108.6
C6—C1—H1A 108.9 C20—C19—H19A 108.6
C2—C1—H1B 108.9 C18—C19—H19B 108.6
C6—C1—H1B 108.9 C20—C19—H19B 108.6
H1A—C1—H1B 107.8 H19A—C19—H19B 107.6
C3—C2—C1 109.71 (19) C29—C20—C30 108.7 (2)
C3—C2—H2A 109.7 C29—C20—C19 108.1 (2)
C1—C2—H2A 109.7 C30—C20—C19 111.7 (2)
C3—C2—H2B 109.7 C29—C20—C21 109.0 (2)
C1—C2—H2B 109.7 C30—C20—C21 111.4 (2)
H2A—C2—H2B 108.2 C19—C20—C21 107.8 (2)
O1—C3—C2 107.98 (18) C22—C21—C20 113.1 (2)
O1—C3—C4 108.78 (18) C22—C21—H21A 109.0
C2—C3—C4 113.5 (2) C20—C21—H21A 109.0
O1—C3—H3 108.8 C22—C21—H21B 109.0
C2—C3—H3 108.8 C20—C21—H21B 109.0
C4—C3—H3 108.8 H21A—C21—H21B 107.8
C24—C4—C23 107.83 (19) C21—C22—C17 113.34 (19)
C24—C4—C3 112.1 (2) C21—C22—H22A 108.9
C23—C4—C3 107.6 (2) C17—C22—H22A 108.9
C24—C4—C5 114.4 (2) C21—C22—H22B 108.9
C23—C4—C5 108.91 (19) C17—C22—H22B 108.9
C3—C4—C5 105.82 (17) H22A—C22—H22B 107.7
C10—C5—C6 110.40 (19) C4—C23—H23A 109.5
C10—C5—C4 114.42 (18) C4—C23—H23B 109.5
C6—C5—C4 117.15 (18) H23A—C23—H23B 109.5
C10—C5—H5 104.4 C4—C23—H23C 109.5
C6—C5—H5 104.4 H23A—C23—H23C 109.5
C4—C5—H5 104.4 H23B—C23—H23C 109.5
C25—C6—C1 108.03 (19) C4—C24—H24A 109.5
C25—C6—C5 114.53 (19) C4—C24—H24B 109.5
C1—C6—C5 108.23 (19) H24A—C24—H24B 109.5
C25—C6—C7 113.15 (19) C4—C24—H24C 109.5
C1—C6—C7 107.43 (17) H24A—C24—H24C 109.5
C5—C6—C7 105.16 (17) H24B—C24—H24C 109.5
C11—C7—C8 110.84 (18) C6—C25—H25A 109.5
C11—C7—C6 113.74 (18) C6—C25—H25B 109.5
C8—C7—C6 117.36 (17) H25A—C25—H25B 109.5
C11—C7—H7 104.5 C6—C25—H25C 109.5
C8—C7—H7 104.5 H25A—C25—H25C 109.5
C6—C7—H7 104.5 H25B—C25—H25C 109.5
C9—C8—C26 106.47 (19) C8—C26—H26A 109.5
C9—C8—C7 110.85 (18) C8—C26—H26B 109.5
C26—C8—C7 111.48 (19) H26A—C26—H26B 109.5
C9—C8—C14 110.53 (18) C8—C26—H26C 109.5
C26—C8—C14 110.96 (19) H26A—C26—H26C 109.5
C7—C8—C14 106.62 (17) H26B—C26—H26C 109.5
C10—C9—C8 113.69 (19) C14—C27—H27A 109.5
C10—C9—H9A 108.8 C14—C27—H27B 109.5
C8—C9—H9A 108.8 H27A—C27—H27B 109.5
C10—C9—H9B 108.8 C14—C27—H27C 109.5
C8—C9—H9B 108.8 H27A—C27—H27C 109.5
H9A—C9—H9B 107.7 H27B—C27—H27C 109.5
C9—C10—C5 110.40 (18) O4—C28—O5 122.3 (2)
C9—C10—H10A 109.6 O4—C28—C17 126.5 (2)
C5—C10—H10A 109.6 O5—C28—C17 111.1 (2)
C9—C10—H10B 109.6 C20—C29—H29A 109.5
C5—C10—H10B 109.6 C20—C29—H29B 109.5
H10A—C10—H10B 108.1 H29A—C29—H29B 109.5
C12—C11—C7 115.97 (18) C20—C29—H29C 109.5
C12—C11—H11A 108.3 H29A—C29—H29C 109.5
C7—C11—H11A 108.3 H29B—C29—H29C 109.5
C12—C11—H11B 108.3 C20—C30—H30A 109.5
C7—C11—H11B 108.3 C20—C30—H30B 109.5
H11A—C11—H11B 107.4 H30A—C30—H30B 109.5
O3—C12—C13 122.5 (2) C20—C30—H30C 109.5
O3—C12—C11 120.04 (19) H30A—C30—H30C 109.5
C13—C12—C11 117.27 (19) H30B—C30—H30C 109.5
C12—C13—C18 113.23 (17) O5—C31—C32 107.4 (2)
C12—C13—C14 112.28 (18) O5—C31—H31A 110.2
C18—C13—C14 116.85 (18) C32—C31—H31A 110.2
C12—C13—H13 104.3 O5—C31—H31B 110.2
C18—C13—H13 104.3 C32—C31—H31B 110.2
C14—C13—H13 104.3 H31A—C31—H31B 108.5
C27—C14—C15 107.85 (18) C37—C32—C33 119.0 (2)
C27—C14—C13 111.32 (18) C37—C32—C31 120.7 (3)
C15—C14—C13 108.69 (18) C33—C32—C31 120.4 (2)
C27—C14—C8 110.22 (18) C32—C33—C34 121.1 (2)
C15—C14—C8 111.08 (17) C32—C33—H33 119.5
C13—C14—C8 107.69 (18) C34—C33—H33 119.5
C16—C15—C14 113.79 (18) C35—C34—C33 119.2 (3)
C16—C15—H15A 108.8 C35—C34—H34 120.4
C14—C15—H15A 108.8 C33—C34—H34 120.4
C16—C15—H15B 108.8 C34—C35—C36 120.6 (3)
C14—C15—H15B 108.8 C34—C35—H35 119.7
H15A—C15—H15B 107.7 C36—C35—H35 119.7
C17—C16—C15 112.36 (19) C35—C36—C37 119.8 (3)
C17—C16—H16A 109.1 C35—C36—H36 120.1
C15—C16—H16A 109.1 C37—C36—H36 120.1
C17—C16—H16B 109.1 C32—C37—C36 120.3 (3)
C15—C16—H16B 109.1 C32—C37—H37 119.8
H16A—C16—H16B 107.9 C36—C37—H37 119.8
C28—C17—C16 110.44 (19) O2—C38—O1 124.5 (2)
C28—C17—C18 109.94 (18) O2—C38—C39 125.1 (2)
C16—C17—C18 109.78 (18) O1—C38—C39 110.4 (2)
C28—C17—C22 104.36 (19) C38—C39—H39A 109.5
C16—C17—C22 111.95 (19) C38—C39—H39B 109.5
C18—C17—C22 110.26 (18) H39A—C39—H39B 109.5
C19—C18—C17 110.94 (18) C38—C39—H39C 109.5
C19—C18—C13 115.12 (18) H39A—C39—H39C 109.5
C17—C18—C13 109.36 (17) H39B—C39—H39C 109.5
C19—C18—H18 107.0
C6—C1—C2—C3 −57.7 (3) C26—C8—C14—C27 −175.96 (17)
C38—O1—C3—C2 124.9 (2) C7—C8—C14—C27 −54.4 (2)
C38—O1—C3—C4 −111.5 (2) C9—C8—C14—C15 −53.3 (2)
C1—C2—C3—O1 −177.77 (19) C26—C8—C14—C15 64.6 (2)
C1—C2—C3—C4 61.5 (3) C7—C8—C14—C15 −173.87 (19)
O1—C3—C4—C24 −51.8 (3) C9—C8—C14—C13 −172.22 (18)
C2—C3—C4—C24 68.4 (3) C26—C8—C14—C13 −54.3 (2)
O1—C3—C4—C23 66.5 (2) C7—C8—C14—C13 67.2 (2)
C2—C3—C4—C23 −173.21 (19) C27—C14—C15—C16 72.6 (2)
O1—C3—C4—C5 −177.16 (18) C13—C14—C15—C16 −48.2 (3)
C2—C3—C4—C5 −56.9 (2) C8—C14—C15—C16 −166.6 (2)
C24—C4—C5—C10 60.5 (3) C14—C15—C16—C17 55.9 (3)
C23—C4—C5—C10 −60.3 (3) C15—C16—C17—C28 62.7 (2)
C3—C4—C5—C10 −175.7 (2) C15—C16—C17—C18 −58.7 (3)
C24—C4—C5—C6 −71.1 (3) C15—C16—C17—C22 178.55 (19)
C23—C4—C5—C6 168.2 (2) C28—C17—C18—C19 166.22 (19)
C3—C4—C5—C6 52.8 (3) C16—C17—C18—C19 −72.1 (2)
C2—C1—C6—C25 −73.3 (2) C22—C17—C18—C19 51.7 (3)
C2—C1—C6—C5 51.3 (3) C28—C17—C18—C13 −65.7 (2)
C2—C1—C6—C7 164.3 (2) C16—C17—C18—C13 55.9 (3)
C10—C5—C6—C25 −63.7 (2) C22—C17—C18—C13 179.73 (19)
C4—C5—C6—C25 69.6 (3) C12—C13—C18—C19 −61.1 (3)
C10—C5—C6—C1 175.72 (18) C14—C13—C18—C19 71.7 (2)
C4—C5—C6—C1 −50.9 (3) C12—C13—C18—C17 173.25 (19)
C10—C5—C6—C7 61.1 (2) C14—C13—C18—C17 −53.9 (3)
C4—C5—C6—C7 −165.52 (19) C17—C18—C19—C20 −56.2 (3)
C25—C6—C7—C11 −59.2 (3) C13—C18—C19—C20 178.95 (19)
C1—C6—C7—C11 59.9 (3) C18—C19—C20—C29 173.4 (2)
C5—C6—C7—C11 175.05 (19) C18—C19—C20—C30 −67.1 (3)
C25—C6—C7—C8 72.5 (3) C18—C19—C20—C21 55.7 (3)
C1—C6—C7—C8 −168.4 (2) C29—C20—C21—C22 −171.2 (2)
C5—C6—C7—C8 −53.3 (3) C30—C20—C21—C22 68.9 (3)
C11—C7—C8—C9 178.83 (19) C19—C20—C21—C22 −54.0 (3)
C6—C7—C8—C9 45.8 (3) C20—C21—C22—C17 54.9 (3)
C11—C7—C8—C26 60.4 (2) C28—C17—C22—C21 −170.27 (19)
C6—C7—C8—C26 −72.6 (3) C16—C17—C22—C21 70.3 (2)
C11—C7—C8—C14 −60.8 (2) C18—C17—C22—C21 −52.3 (3)
C6—C7—C8—C14 166.19 (19) C31—O5—C28—O4 −0.4 (4)
C26—C8—C9—C10 76.6 (2) C31—O5—C28—C17 176.0 (2)
C7—C8—C9—C10 −44.8 (3) C16—C17—C28—O4 −137.1 (2)
C14—C8—C9—C10 −162.80 (19) C18—C17—C28—O4 −15.8 (3)
C8—C9—C10—C5 55.7 (3) C22—C17—C28—O4 102.4 (3)
C6—C5—C10—C9 −65.2 (3) C16—C17—C28—O5 46.6 (3)
C4—C5—C10—C9 160.1 (2) C18—C17—C28—O5 167.90 (18)
C8—C7—C11—C12 45.3 (3) C22—C17—C28—O5 −73.9 (2)
C6—C7—C11—C12 −179.96 (19) C28—O5—C31—C32 −174.5 (2)
C7—C11—C12—O3 149.9 (2) O5—C31—C32—C37 91.0 (3)
C7—C11—C12—C13 −35.4 (3) O5—C31—C32—C33 −89.4 (3)
O3—C12—C13—C18 −8.7 (3) C37—C32—C33—C34 −0.2 (4)
C11—C12—C13—C18 176.7 (2) C31—C32—C33—C34 −179.9 (3)
O3—C12—C13—C14 −143.7 (2) C32—C33—C34—C35 0.2 (4)
C11—C12—C13—C14 41.7 (3) C33—C34—C35—C36 0.7 (5)
C12—C13—C14—C27 63.6 (2) C34—C35—C36—C37 −1.5 (5)
C18—C13—C14—C27 −69.7 (2) C33—C32—C37—C36 −0.5 (4)
C12—C13—C14—C15 −177.79 (19) C31—C32—C37—C36 179.1 (3)
C18—C13—C14—C15 49.0 (3) C35—C36—C37—C32 1.4 (5)
C12—C13—C14—C8 −57.4 (2) C3—O1—C38—O2 −6.1 (3)
C18—C13—C14—C8 169.39 (18) C3—O1—C38—C39 173.1 (2)
C9—C8—C14—C27 66.2 (2)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2003).

References

  1. 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.
  2. Honda, Y., Honda, T., Roy, S. & Gribble, G. W. (2003). J. Org. Chem. 68, 4991–4993. [DOI] [PubMed]
  3. Liu, J. (1995). J. Ethnopharmacol. 49, 57–68. [DOI] [PubMed]
  4. Matsuda, H., Li, Y. H., Murakami, T., Yamahara, J. & Yoshikawa, M. (1999). Bioorg. Med. Chem. 7, 323–327. [DOI] [PubMed]
  5. Rigaku/MSC (2005). CrystalClear Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Sun, H.-X., Ye, Y.-P., Wang, K.-W. & Pan, Y.-J. (2003). Acta Cryst. E59, o989–o991.

Associated Data

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

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010968/yk2003sup1.cif

e-67-o1027-sup1.cif (32.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010968/yk2003Isup2.hkl

e-67-o1027-Isup2.hkl (225.7KB, 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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