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3β,6β-Di­hydroxy­olean-12-en-27-oic acid, C30H48O4, a cytotoxic and apoptosis-inducing oleanane triterpenoid, which was isolated from the rhizome of Astilbe chinensis, consists of a linear array of five fused six-membered rings. The central ring has a slightly distorted half-chair conformation, while the four outer rings adopt chair conformations. Two hydroxy groups and one carboxy group serve simultaneously as hydrogen-bond donors and acceptors, forming molecular chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104005530/fa1051sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104005530/fa1051Isup2.hkl
Contains datablock I

CCDC reference: 237954

Comment top

Astilbe chinensis (Haxim.) Franch. et Savat. (Saxiffagaceae) is a perennial herbaceous plant growing at an altitude of 390–3600 m in China, Russia Japan and Korea. Its rhizome, known as 'Luo Xinfu' (Chinese name), has been used for headache, arthralgia, chronic bronchitis and stomachalgia in traditional Chinese medicine (Pan, 1985, 1995). Pharmacological experiments indicate that extracts from A. chinensis have antineoplastic and immunopotentiating activities (Chen et al., 1996). Previously, we have isolated β-sitosterol palmitate, daucosterol, β-sitosterol and bergenin from the rhizome of A. chinensis (Sun et al., 2002). To investigate the bioactive natural products from A. chinensis, chemical studies on the rhizome of A. chinensis were undertaken by screening using antineoplastic tests in vitro, and we have obtained a cytotoxic and apoptotic-inducing triterpenoid, 3β,6β-dihydroxyolean-12-en-27-oic acid, (I), from the petroleum ether extract. Compound (I) exhibits significant cytotoxic activity against the human ovarian carcinoma cell (HO-8910), the human cervical squamous carcinoma cell (Hela), the human leukemia cell (HL60), the human colorectal carcinoma cell line (COLO 205), human androgen-independent prostate adenocarcinoma (PC3), human breast cancer (Bcap37) and human chronic myelogenous leukemia (K562) in vitro. The 50% inhibitory concentration (IC50) values are 22.24 (0.57), 11.91 (1.02), 24.24 (3.82), 29.08 (0.16), 30.59 (2.56), 28.91 (0.76) and 31.08 (0.92) µg ml−1, respectively. Moreover, (I) induced apoptosis of COLO 205 by disturbing DNA replication, down-regulating bcl-2 expression and up-regulating bax expression, lowering relative mitochondrial transmembrane potential and activating caspase-3 pathway (Sun et al., 2004). The structure of (I) was elucidated by extensive spectroscopic analysis including two-dimensional NMR spectroscopy and confirmed by single-crystal X-ray diffraction analysis.

Compound (I) was obtained as colorless prisms in the orthorhombic space group P212121. Our X-ray data allowed determination of the relative stereochemistry of the molecules in the crystal studied; a view of the molecule of (I) with our numbering scheme is shown in Fig. 1 and selected dimensions are given in Table 1. The molecule is composed of five six-membered rings, viz. A (C1–C5/C10), B (C5–C10), C (C8/C9/C11–C14), (D (C13–C18) and E (C17–C22). Rings A, B, D and E adopt chair conformations, while ring C adopts a slightly distorted half-chair conformation as a result of the double bond between atoms C12 and C13. All rings are trans fused, except for the D/E junction, which is cis fused. The configurations at the other chiral centers are as follows: C5—H, C6—OH, C18—H, C8—Me, C17—Me and the carboxy group at C14 are axial, and C3–OH is equatorial.

The hydroxy groups located at stoms C3 and C6, and the carboxy group located at atom C14, participate in hydrogen bonding. The three groups serve simultaneously as hydrogen-bond donors and acceptors (Table 2), resulting in three intermolecular O—H···O hydrogen bonds. All of the hydrogen bonds are between molecules of different asymmetric units. The significant inhibitory effect of I on the HO-8910, Hela, HL60, COLO 205, PC3, Bcap37 and K562 cell lines in vitro, and the elevated 50% inhibitory concentration (IC50) values of its disodiumphosphate, implied that the hydroxy groups help the molecule to bind to enzymes in the tumor cell and that these groups are implicated in inhibitory activity.

Experimental top

The rhizomes of A. chinensis were collected in Anji county, Zhejiang Province, Peopl's Republic of China, in August 2001. The plants were identified as A. chinensis (Haxim.) Franch. et Savat. by Professor Xiang-Ji Xue, College of Pharmaceutical Science, Zhejiang University. A voucher specimen (No. 200120) was deposited in the Laboratory of Nature and Biochemistry, Zhejiang University. The rhizomes of A. chinensis were dried in the dark, in a ventilated hood, and ground. The material (5.0 kg) was extracted three times with MeOH (each 25 l) at room temperature. The MeOH extract (366 g) was partitioned between petroleum ether (20 l) and water (2 l). The petroleum ether solution was concentrated in vacuo to give of a gelatinous material (41.2 g). Part of the extract (40.0 g) was absorbed onto silica gel (60 g) and chromatographied on a silica-gel (600 g) column eluted with petroleum ether–EtoAc (50:1, 30:1, 15:1, 5:1, 3:1, 2:1) gradients. The eluted fractions were evaluated by thin-layer chromatography and combined to give Frs. 1–19, respectively. Fr. 13 was recrystallized with EtOAC–CH3OH (1:1) to afford the pure title compound, (I) (4.2 g, m.p. 512–514 K). 13C NMR (125 MHz, C5ND5, p.p.m): 179.8 (C27), 133.2 (C13), 128.5(C12), 79.1 (C3), 60.2 (C18), 55.9 (C14), 55.1 (C5), 46.8 (C9), 40.9 (C22), 39.8 (C19), 39.8 (C8), 38.7 (C1), 38.6 (C4), 37.5 (C20), 36.9 (C10), 36.6 (C7), 33.7 (C17), 30.4 (C21), 29.0 (C28), 28.9 (C16), 28.1 (C23), 27.0 (C2), 22.7 (C11), 22.4 (C15), 21.3 (C30), 18.2 (C6), 18.2 (C26), 17.8 (C29), 16.5 (C25), 15.7 (C24). Crystals suitable for X-ray structure analysis were obtained by slow evaporation from the methanol solvent at room temperature.

Refinement top

Hydroxy atoms H10, H20 and H40 were located from diffraction measurements and refined with distance restraints on their bonds to atoms O1, O2 and O4, respectively. Other H atoms were placed at calculated positions and allowed to ride on their parent atoms using SHELXL97 (Sheldrick, 1997) defaults. The absolute structure could not be refined because of the absence of significant anomalous effects. Friedel pairs were merged before the final cycles of the refinement.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL/PC (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Figures top
[Figure 1] Fig. 1. A view of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The intermolecular hydrogen bonding in (I), viewed normal to the (001) plane. H atoms have been omitted for clarity, except for those involved in hydrogen bonds. Hydrogen bonds are shown as dashed lines.
3β,6β-dihydroxy-olean-12-en-27-oic acid top
Crystal data top
C30H48O4Dx = 1.199 Mg m3
Mr = 472.68Melting point: 513 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 12.016 (2) ÅCell parameters from 36 reflections
b = 14.141 (2) Åθ = 5.8–14.2°
c = 15.406 (2) ŵ = 0.08 mm1
V = 2617.6 (4) Å3T = 288 K
Z = 4Prism, colorless
F(000) = 10400.58 × 0.58 × 0.38 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.007
Radiation source: normal-focus sealed tubeθmax = 27.0°, θmin = 2.0°
Graphite monochromatorh = 015
ω scansk = 018
3481 measured reflectionsl = 119
3209 independent reflections3 standard reflections every 97 reflections
2549 reflections with I > 2σ(I) intensity decay: 2.1%
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)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0509P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max < 0.001
3209 reflectionsΔρmax = 0.22 e Å3
327 parametersΔρmin = 0.16 e Å3
3 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0030 (5)
Crystal data top
C30H48O4V = 2617.6 (4) Å3
Mr = 472.68Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.016 (2) ŵ = 0.08 mm1
b = 14.141 (2) ÅT = 288 K
c = 15.406 (2) Å0.58 × 0.58 × 0.38 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.007
3481 measured reflections3 standard reflections every 97 reflections
3209 independent reflections intensity decay: 2.1%
2549 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0373 restraints
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.22 e Å3
3209 reflectionsΔρmin = 0.16 e Å3
327 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
O10.41431 (16)0.56850 (12)0.80579 (11)0.0381 (4)
O20.59346 (14)0.25242 (11)0.63496 (11)0.0348 (4)
O30.32604 (13)0.41372 (12)0.35577 (11)0.0371 (4)
O40.31939 (14)0.25658 (13)0.34323 (13)0.0434 (5)
C10.53468 (19)0.56935 (15)0.58009 (14)0.0265 (5)
H1A0.59200.60950.55540.032*
H1B0.46660.58080.54800.032*
C20.5163 (2)0.59848 (16)0.67434 (15)0.0325 (6)
H2A0.58660.59630.70520.039*
H2B0.48900.66300.67630.039*
C30.4335 (2)0.53390 (15)0.71851 (14)0.0287 (5)
H30.36310.53810.68670.034*
C40.47061 (18)0.42926 (15)0.71842 (14)0.0265 (5)
C50.48714 (17)0.40284 (14)0.62007 (14)0.0219 (4)
H50.41500.41990.59480.026*
C60.49456 (19)0.29644 (14)0.60042 (14)0.0245 (5)
H60.43130.26680.63000.029*
C70.47814 (19)0.27848 (14)0.50355 (14)0.0255 (5)
H7A0.40080.29100.48970.031*
H7B0.49130.21180.49270.031*
C80.55112 (17)0.33587 (14)0.44020 (14)0.0216 (4)
C90.54956 (18)0.44216 (14)0.46777 (13)0.0210 (4)
H90.47360.46370.45580.025*
C100.56922 (17)0.46450 (14)0.56680 (14)0.0218 (5)
C110.6234 (2)0.50020 (16)0.40749 (14)0.0294 (5)
H11A0.60970.56690.41750.035*
H11B0.70080.48760.42110.035*
C120.60304 (18)0.47827 (15)0.31432 (14)0.0264 (5)
H120.63210.52040.27380.032*
C130.54763 (17)0.40468 (15)0.28359 (14)0.0229 (5)
C140.50139 (18)0.32693 (14)0.34306 (14)0.0230 (5)
C150.5305 (2)0.22913 (15)0.30318 (15)0.0299 (5)
H15A0.60880.21650.31340.036*
H15B0.48820.18090.33340.036*
C160.5075 (2)0.22026 (15)0.20549 (15)0.0335 (6)
H16A0.53170.15850.18570.040*
H16B0.42800.22500.19550.040*
C170.56720 (19)0.29681 (16)0.15263 (15)0.0282 (5)
C180.53032 (18)0.39438 (15)0.18595 (14)0.0241 (5)
H180.57990.44060.15850.029*
C190.41134 (19)0.41996 (17)0.15634 (15)0.0312 (5)
H19A0.35910.37620.18260.037*
H19B0.39330.48300.17670.037*
C200.3980 (2)0.41655 (19)0.05701 (16)0.0366 (6)
C210.4278 (2)0.31673 (19)0.02688 (16)0.0397 (6)
H21A0.37370.27260.05010.048*
H21B0.42320.31410.03590.048*
C220.5428 (2)0.28644 (19)0.05488 (16)0.0374 (6)
H22A0.59710.32350.02290.045*
H22B0.55330.22070.03880.045*
C230.3744 (2)0.37145 (16)0.75525 (16)0.0363 (6)
H23A0.39740.30690.76240.044*
H23B0.31240.37410.71600.044*
H23C0.35270.39700.81050.044*
C240.5715 (2)0.41357 (18)0.77786 (15)0.0376 (6)
H24A0.54880.41960.83740.045*
H24B0.62750.45990.76510.045*
H24C0.60110.35140.76830.045*
C250.69269 (18)0.45571 (16)0.59580 (15)0.0296 (5)
H25A0.70540.49540.64540.036*
H25B0.74050.47510.54920.036*
H25C0.70840.39120.61080.036*
C260.67168 (19)0.29729 (16)0.44107 (16)0.0313 (5)
H26A0.70790.31630.49380.038*
H26B0.71170.32220.39220.038*
H26C0.67010.22950.43770.038*
C270.37316 (19)0.33784 (16)0.34782 (14)0.0269 (5)
C280.69407 (19)0.28671 (19)0.16289 (17)0.0394 (6)
H28A0.71680.22520.14340.047*
H28B0.71380.29440.22290.047*
H28C0.73070.33430.12880.047*
C290.2759 (2)0.4348 (3)0.03349 (19)0.0624 (9)
H29A0.26700.43170.02840.075*
H29B0.25430.49630.05370.075*
H29C0.22980.38770.06040.075*
C300.4695 (3)0.49310 (19)0.01424 (17)0.0558 (9)
H30A0.54680.47850.02260.067*
H30B0.45310.55330.04010.067*
H30C0.45340.49550.04680.067*
H1O0.3520 (14)0.552 (2)0.822 (2)0.077 (13)*
H2O0.575 (2)0.1992 (11)0.6498 (19)0.053 (9)*
H4O0.2520 (10)0.265 (2)0.347 (2)0.075 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0493 (12)0.0345 (9)0.0305 (9)0.0014 (9)0.0061 (9)0.0078 (8)
O20.0380 (10)0.0246 (8)0.0420 (10)0.0053 (8)0.0054 (8)0.0077 (8)
O30.0263 (8)0.0430 (10)0.0420 (10)0.0056 (8)0.0012 (8)0.0035 (8)
O40.0287 (10)0.0413 (10)0.0602 (12)0.0150 (9)0.0005 (9)0.0013 (9)
C10.0282 (12)0.0201 (10)0.0311 (12)0.0027 (9)0.0016 (10)0.0018 (9)
C20.0424 (14)0.0223 (11)0.0329 (13)0.0019 (11)0.0013 (11)0.0024 (10)
C30.0338 (13)0.0281 (11)0.0242 (11)0.0025 (10)0.0001 (10)0.0042 (9)
C40.0304 (12)0.0247 (10)0.0245 (11)0.0014 (10)0.0003 (10)0.0004 (9)
C50.0217 (10)0.0190 (9)0.0249 (11)0.0006 (9)0.0024 (9)0.0028 (9)
C60.0271 (12)0.0191 (10)0.0274 (12)0.0018 (10)0.0002 (10)0.0033 (9)
C70.0302 (12)0.0175 (9)0.0288 (12)0.0015 (9)0.0006 (10)0.0007 (9)
C80.0216 (11)0.0186 (9)0.0248 (11)0.0032 (9)0.0004 (9)0.0014 (9)
C90.0209 (10)0.0188 (10)0.0232 (11)0.0012 (8)0.0017 (9)0.0035 (9)
C100.0216 (10)0.0199 (10)0.0240 (11)0.0012 (9)0.0017 (9)0.0010 (9)
C110.0325 (13)0.0261 (11)0.0294 (12)0.0091 (10)0.0009 (11)0.0023 (10)
C120.0296 (12)0.0234 (11)0.0262 (11)0.0041 (10)0.0031 (10)0.0056 (9)
C130.0222 (11)0.0219 (10)0.0246 (11)0.0032 (9)0.0021 (9)0.0010 (9)
C140.0232 (10)0.0197 (10)0.0261 (11)0.0009 (9)0.0000 (10)0.0008 (9)
C150.0337 (13)0.0227 (11)0.0334 (12)0.0025 (10)0.0010 (11)0.0001 (10)
C160.0402 (14)0.0244 (11)0.0358 (13)0.0005 (11)0.0032 (12)0.0067 (10)
C170.0288 (12)0.0265 (11)0.0293 (12)0.0031 (10)0.0003 (10)0.0024 (10)
C180.0246 (11)0.0240 (11)0.0236 (11)0.0004 (10)0.0009 (9)0.0009 (9)
C190.0318 (12)0.0340 (13)0.0279 (12)0.0073 (11)0.0010 (10)0.0004 (11)
C200.0339 (13)0.0491 (15)0.0267 (12)0.0120 (12)0.0044 (11)0.0006 (12)
C210.0420 (15)0.0498 (16)0.0273 (13)0.0011 (13)0.0053 (12)0.0070 (12)
C220.0425 (14)0.0379 (13)0.0317 (13)0.0044 (12)0.0017 (12)0.0076 (11)
C230.0469 (15)0.0304 (12)0.0316 (13)0.0051 (12)0.0112 (12)0.0011 (11)
C240.0451 (15)0.0379 (13)0.0297 (13)0.0062 (12)0.0047 (12)0.0014 (11)
C250.0257 (12)0.0335 (12)0.0295 (12)0.0035 (10)0.0033 (10)0.0011 (10)
C260.0302 (12)0.0315 (12)0.0322 (12)0.0065 (11)0.0035 (11)0.0013 (11)
C270.0267 (11)0.0333 (12)0.0208 (11)0.0052 (11)0.0013 (10)0.0007 (10)
C280.0315 (13)0.0440 (14)0.0425 (15)0.0090 (12)0.0035 (12)0.0002 (12)
C290.0491 (18)0.098 (3)0.0399 (17)0.0270 (18)0.0109 (14)0.0056 (17)
C300.086 (2)0.0484 (17)0.0335 (15)0.0080 (17)0.0013 (16)0.0053 (13)
Geometric parameters (Å, º) top
O1—C31.449 (3)C15—C161.535 (3)
O1—H1O0.826 (10)C15—H15A0.9700
O2—C61.443 (3)C15—H15B0.9700
O2—H2O0.817 (10)C16—C171.533 (3)
O3—C271.219 (3)C16—H16A0.9700
O4—C271.320 (3)C16—H16B0.9700
O4—H4O0.820 (10)C17—C181.537 (3)
C1—C21.525 (3)C17—C281.539 (3)
C1—C101.553 (3)C17—C221.541 (3)
C1—H1A0.9700C18—C191.544 (3)
C1—H1B0.9700C18—H180.9800
C2—C31.512 (3)C19—C201.539 (3)
C2—H2A0.9700C19—H19A0.9700
C2—H2B0.9700C19—H19B0.9700
C3—C41.546 (3)C20—C211.528 (4)
C3—H30.9800C20—C301.531 (4)
C4—C231.526 (3)C20—C291.534 (4)
C4—C241.535 (3)C21—C221.510 (3)
C4—C51.573 (3)C21—H21A0.9700
C5—C61.537 (3)C21—H21B0.9700
C5—C101.551 (3)C22—H22A0.9700
C5—H50.9800C22—H22B0.9700
C6—C71.527 (3)C23—H23A0.9600
C6—H60.9800C23—H23B0.9600
C7—C81.543 (3)C23—H23C0.9600
C7—H7A0.9700C24—H24A0.9600
C7—H7B0.9700C24—H24B0.9600
C8—C261.548 (3)C24—H24C0.9600
C8—C91.562 (3)C25—H25A0.9600
C8—C141.616 (3)C25—H25B0.9600
C9—C111.524 (3)C25—H25C0.9600
C9—C101.576 (3)C26—H26A0.9600
C9—H90.9800C26—H26B0.9600
C10—C251.554 (3)C26—H26C0.9600
C11—C121.489 (3)C28—H28A0.9600
C11—H11A0.9700C28—H28B0.9600
C11—H11B0.9700C28—H28C0.9600
C12—C131.323 (3)C29—H29A0.9600
C12—H120.9300C29—H29B0.9600
C13—C181.526 (3)C29—H29C0.9600
C13—C141.535 (3)C30—H30A0.9600
C14—C271.550 (3)C30—H30B0.9600
C14—C151.553 (3)C30—H30C0.9600
C3—O1—H1O109 (2)C17—C16—C15112.24 (19)
C6—O2—H2O106 (2)C17—C16—H16A109.2
C27—O4—H4O111 (2)C15—C16—H16A109.2
C2—C1—C10114.96 (18)C17—C16—H16B109.2
C2—C1—H1A108.5C15—C16—H16B109.2
C10—C1—H1A108.5H16A—C16—H16B107.9
C2—C1—H1B108.5C16—C17—C18108.74 (18)
C10—C1—H1B108.5C16—C17—C28110.1 (2)
H1A—C1—H1B107.5C18—C17—C28109.54 (19)
C3—C2—C1111.13 (19)C16—C17—C22111.3 (2)
C3—C2—H2A109.4C18—C17—C22110.91 (19)
C1—C2—H2A109.4C28—C17—C22106.2 (2)
C3—C2—H2B109.4C13—C18—C17112.06 (18)
C1—C2—H2B109.4C13—C18—C19113.28 (19)
H2A—C2—H2B108.0C17—C18—C19112.25 (18)
O1—C3—C2108.56 (18)C13—C18—H18106.2
O1—C3—C4111.71 (18)C17—C18—H18106.2
C2—C3—C4112.83 (19)C19—C18—H18106.2
O1—C3—H3107.9C20—C19—C18112.51 (19)
C2—C3—H3107.9C20—C19—H19A109.1
C4—C3—H3107.9C18—C19—H19A109.1
C23—C4—C24107.41 (19)C20—C19—H19B109.1
C23—C4—C3107.09 (19)C18—C19—H19B109.1
C24—C4—C3111.45 (18)H19A—C19—H19B107.8
C23—C4—C5109.06 (18)C21—C20—C30113.0 (2)
C24—C4—C5116.14 (18)C21—C20—C29107.9 (2)
C3—C4—C5105.34 (17)C30—C20—C29108.5 (2)
C6—C5—C10114.14 (17)C21—C20—C19107.9 (2)
C6—C5—C4115.43 (17)C30—C20—C19110.3 (2)
C10—C5—C4117.15 (17)C29—C20—C19109.2 (2)
C6—C5—H5102.3C22—C21—C20112.9 (2)
C10—C5—H5102.3C22—C21—H21A109.0
C4—C5—H5102.3C20—C21—H21A109.0
O2—C6—C7113.27 (18)C22—C21—H21B109.0
O2—C6—C5113.40 (17)C20—C21—H21B109.0
C7—C6—C5110.36 (17)H21A—C21—H21B107.8
O2—C6—H6106.4C21—C22—C17115.2 (2)
C7—C6—H6106.4C21—C22—H22A108.5
C5—C6—H6106.4C17—C22—H22A108.5
C6—C7—C8117.22 (18)C21—C22—H22B108.5
C6—C7—H7A108.0C17—C22—H22B108.5
C8—C7—H7A108.0H22A—C22—H22B107.5
C6—C7—H7B108.0C4—C23—H23A109.5
C8—C7—H7B108.0C4—C23—H23B109.5
H7A—C7—H7B107.2H23A—C23—H23B109.5
C7—C8—C26109.95 (17)C4—C23—H23C109.5
C7—C8—C9109.11 (17)H23A—C23—H23C109.5
C26—C8—C9110.36 (17)H23B—C23—H23C109.5
C7—C8—C14109.54 (16)C4—C24—H24A109.5
C26—C8—C14109.05 (17)C4—C24—H24B109.5
C9—C8—C14108.82 (16)H24A—C24—H24B109.5
C11—C9—C8110.21 (17)C4—C24—H24C109.5
C11—C9—C10113.24 (17)H24A—C24—H24C109.5
C8—C9—C10117.02 (16)H24B—C24—H24C109.5
C11—C9—H9105.0C10—C25—H25A109.5
C8—C9—H9105.0C10—C25—H25B109.5
C10—C9—H9105.0H25A—C25—H25B109.5
C5—C10—C1107.27 (17)C10—C25—H25C109.5
C5—C10—C25114.20 (17)H25A—C25—H25C109.5
C1—C10—C25107.06 (17)H25B—C25—H25C109.5
C5—C10—C9107.71 (16)C8—C26—H26A109.5
C1—C10—C9106.20 (16)C8—C26—H26B109.5
C25—C10—C9113.91 (17)H26A—C26—H26B109.5
C12—C11—C9112.30 (18)C8—C26—H26C109.5
C12—C11—H11A109.1H26A—C26—H26C109.5
C9—C11—H11A109.1H26B—C26—H26C109.5
C12—C11—H11B109.1O3—C27—O4123.0 (2)
C9—C11—H11B109.1O3—C27—C14123.6 (2)
H11A—C11—H11B107.9O4—C27—C14113.4 (2)
C13—C12—C11126.3 (2)C17—C28—H28A109.5
C13—C12—H12116.9C17—C28—H28B109.5
C11—C12—H12116.9H28A—C28—H28B109.5
C12—C13—C18119.8 (2)C17—C28—H28C109.5
C12—C13—C14122.1 (2)H28A—C28—H28C109.5
C18—C13—C14118.09 (18)H28B—C28—H28C109.5
C13—C14—C27108.46 (18)C20—C29—H29A109.5
C13—C14—C15108.67 (17)C20—C29—H29B109.5
C27—C14—C15109.34 (18)H29A—C29—H29B109.5
C13—C14—C8111.27 (16)C20—C29—H29C109.5
C27—C14—C8108.42 (17)H29A—C29—H29C109.5
C15—C14—C8110.64 (17)H29B—C29—H29C109.5
C16—C15—C14114.82 (18)C20—C30—H30A109.5
C16—C15—H15A108.6C20—C30—H30B109.5
C14—C15—H15A108.6H30A—C30—H30B109.5
C16—C15—H15B108.6C20—C30—H30C109.5
C14—C15—H15B108.6H30A—C30—H30C109.5
H15A—C15—H15B107.5H30B—C30—H30C109.5
C10—C1—C2—C354.3 (3)C12—C13—C14—C27107.1 (2)
C1—C2—C3—O1176.49 (19)C18—C13—C14—C2774.2 (2)
C1—C2—C3—C459.1 (3)C12—C13—C14—C15134.1 (2)
O1—C3—C4—C2363.7 (2)C18—C13—C14—C1544.6 (3)
C2—C3—C4—C23173.67 (19)C12—C13—C14—C812.0 (3)
O1—C3—C4—C2453.5 (3)C18—C13—C14—C8166.68 (18)
C2—C3—C4—C2469.1 (2)C7—C8—C14—C13162.73 (17)
O1—C3—C4—C5179.73 (18)C26—C8—C14—C1376.9 (2)
C2—C3—C4—C557.6 (2)C9—C8—C14—C1343.5 (2)
C23—C4—C5—C650.1 (2)C7—C8—C14—C2743.5 (2)
C24—C4—C5—C671.4 (3)C26—C8—C14—C27163.90 (17)
C3—C4—C5—C6164.77 (18)C9—C8—C14—C2775.7 (2)
C23—C4—C5—C10171.05 (18)C7—C8—C14—C1576.4 (2)
C24—C4—C5—C1067.5 (2)C26—C8—C14—C1544.0 (2)
C3—C4—C5—C1056.4 (2)C9—C8—C14—C15164.44 (17)
C10—C5—C6—O272.7 (2)C13—C14—C15—C1646.2 (3)
C4—C5—C6—O267.3 (2)C27—C14—C15—C1672.1 (2)
C10—C5—C6—C755.6 (2)C8—C14—C15—C16168.61 (18)
C4—C5—C6—C7164.36 (18)C14—C15—C16—C1755.8 (3)
O2—C6—C7—C876.6 (2)C15—C16—C17—C1857.6 (2)
C5—C6—C7—C851.7 (3)C15—C16—C17—C2862.5 (3)
C6—C7—C8—C2674.3 (2)C15—C16—C17—C22179.99 (19)
C6—C7—C8—C946.9 (2)C12—C13—C18—C17127.9 (2)
C6—C7—C8—C14165.93 (18)C14—C13—C18—C1750.9 (3)
C7—C8—C9—C11178.62 (18)C12—C13—C18—C19103.9 (2)
C26—C8—C9—C1157.7 (2)C14—C13—C18—C1977.4 (2)
C14—C8—C9—C1161.9 (2)C16—C17—C18—C1354.2 (2)
C7—C8—C9—C1047.3 (2)C28—C17—C18—C1366.2 (2)
C26—C8—C9—C1073.6 (2)C22—C17—C18—C13176.89 (19)
C14—C8—C9—C10166.80 (17)C16—C17—C18—C1974.6 (2)
C6—C5—C10—C1168.63 (17)C28—C17—C18—C19165.0 (2)
C4—C5—C10—C152.0 (2)C22—C17—C18—C1948.1 (2)
C6—C5—C10—C2572.9 (2)C13—C18—C19—C20175.6 (2)
C4—C5—C10—C2566.4 (2)C17—C18—C19—C2056.2 (3)
C6—C5—C10—C954.7 (2)C18—C19—C20—C2158.4 (3)
C4—C5—C10—C9165.97 (17)C18—C19—C20—C3065.5 (3)
C2—C1—C10—C548.9 (2)C18—C19—C20—C29175.4 (2)
C2—C1—C10—C2574.1 (2)C30—C20—C21—C2266.2 (3)
C2—C1—C10—C9163.86 (19)C29—C20—C21—C22173.9 (2)
C11—C9—C10—C5178.56 (18)C19—C20—C21—C2256.0 (3)
C8—C9—C10—C551.6 (2)C20—C21—C22—C1752.6 (3)
C11—C9—C10—C163.9 (2)C16—C17—C22—C2174.1 (3)
C8—C9—C10—C1166.23 (17)C18—C17—C22—C2147.1 (3)
C11—C9—C10—C2553.7 (2)C28—C17—C22—C21166.1 (2)
C8—C9—C10—C2576.2 (2)C13—C14—C27—O343.0 (3)
C8—C9—C11—C1247.0 (2)C15—C14—C27—O3161.4 (2)
C10—C9—C11—C12179.72 (19)C8—C14—C27—O377.9 (3)
C9—C11—C12—C1314.2 (3)C13—C14—C27—O4137.59 (19)
C11—C12—C13—C18177.7 (2)C15—C14—C27—O419.2 (3)
C11—C12—C13—C143.6 (4)C8—C14—C27—O4101.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O3i0.83 (1)2.26 (2)2.999 (2)150 (3)
O2—H2O···O1ii0.82 (1)1.98 (1)2.758 (2)160 (3)
O4—H4O···O2iii0.82 (1)1.94 (1)2.738 (2)164 (3)
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x+1, y1/2, z+3/2; (iii) x1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC30H48O4
Mr472.68
Crystal system, space groupOrthorhombic, P212121
Temperature (K)288
a, b, c (Å)12.016 (2), 14.141 (2), 15.406 (2)
V3)2617.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.58 × 0.58 × 0.38
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3481, 3209, 2549
Rint0.007
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.086, 0.94
No. of reflections3209
No. of parameters327
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.16

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL/PC (Siemens, 1991), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL/PC.

Selected geometric parameters (Å, º) top
O1—C31.449 (3)C8—C141.616 (3)
O2—C61.443 (3)C11—C121.489 (3)
O3—C271.219 (3)C12—C131.323 (3)
O4—C271.320 (3)
O1—C3—C2108.56 (18)C12—C13—C18119.8 (2)
O1—C3—C4111.71 (18)C12—C13—C14122.1 (2)
C2—C3—C4112.83 (19)C18—C13—C14118.09 (18)
O2—C6—C7113.27 (18)O3—C27—O4123.0 (2)
O2—C6—C5113.40 (17)O3—C27—C14123.6 (2)
C7—C6—C5110.36 (17)O4—C27—C14113.4 (2)
C1—C2—C3—O1176.49 (19)C13—C14—C27—O343.0 (3)
O1—C3—C4—C2363.7 (2)C15—C14—C27—O3161.4 (2)
O1—C3—C4—C2453.5 (3)C8—C14—C27—O377.9 (3)
O1—C3—C4—C5179.73 (18)C13—C14—C27—O4137.59 (19)
C10—C5—C6—O272.7 (2)C15—C14—C27—O419.2 (3)
C4—C5—C6—O267.3 (2)C8—C14—C27—O4101.5 (2)
O2—C6—C7—C876.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O3i0.826 (10)2.255 (19)2.999 (2)150 (3)
O2—H2O···O1ii0.817 (10)1.975 (14)2.758 (2)160 (3)
O4—H4O···O2iii0.820 (10)1.940 (14)2.738 (2)164 (3)
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x+1, y1/2, z+3/2; (iii) x1/2, y+1/2, z+1.
 

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