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Acta Cryst. (2009). E65, o2113    [ doi:10.1107/S1600536809030669 ]

Methyl 3-dehydroxy-3-oxoursolate

K. Awang, N. H. Abdullah, N. F. Thomas and S. W. Ng

Abstract top

Four of the five six-membered rings of the title pentacylic triterpene, C31H48O3, adopt chair conformations; the fifth, which has a C=C double bond, adopts an approximate envelope conformation.

Related literature top

The structure was previously refined to an R-index of 0.043 but atomic coordinates were not published. The reported room-temperature cell [8.109 (1), 8.618 (1), 39.148 (1) Å] is slightly larger; see: de Vivar et al. (1985). For the synthesis, see: Honda et al. (1997); Ma et al. (2005); Zhao et al. (2007).

Experimental top

The dried leaves of Primsatomoris malayana Ridley (Rubiaceae) (2 kg) were extracted with methanol (10 L). The extract was concentrated and then partitioned with petroleum ether, chloroform and ethyl acetate. The chloroform fraction (35 g) was dissolved in methanol and subjected to column chromatography by using Diaion HP-20 with methanol as the eluent to furnish 200 fractions. After confirming that the fractions contained the same material by TLC analysis, the fractions were pooled into 3 sub-fractions. One sub-fraction was purified by using column chromatography on silica gel (chloroform/methanol10:0 → 9:1) to give ursolic acid (5 g), which was identified acid from its NMR and mass spectra.

The ursolic acid was treated with trimethylsilyl diazomethane and pyridinium chlorochromate according to a literature method. The compound was purified by chromatography with a hexane and chloroform system (Ma et al., 2005). Crystals were isolated when the solvent was allowed to evaporate.

Refinement top

The carbon-bound H-atoms were generated geometrically (C—H 0.95–0.99 Å) and were allowed to ride on their parent atoms, with U(H) fixed at 1.2–1.5Ueq(C). Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker,2008); program(s) used to solve structure: SHELX97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of methyl 3-dehydroursolate. Displacement ellipsoids are drawn at the 70% probability level, and hydrogen atoms are drawn as spheres of arbitrary radius.
Methyl 3-dehydroxy-3-oxoursolate top
Crystal data top
C31H48O3F(000) = 1032
Mr = 468.69Dx = 1.171 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4540 reflections
a = 8.0298 (2) Åθ = 2.5–28.2°
b = 8.4775 (2) ŵ = 0.07 mm−1
c = 39.0492 (7) ÅT = 100 K
V = 2658.2 (1) Å3Block, colorless
Z = 40.25 × 0.15 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer		3188 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
graphiteθmax = 27.5°, θmin = 1.0°
ω scansh = −10→10
18588 measured reflectionsk = −11→10
3500 independent reflectionsl = −50→49
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-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0528P)2 + 0.4713P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3500 reflectionsΔρmax = 0.27 e Å−3
315 parametersΔρmin = −0.18 e Å−3
0 restraintsAbsolute structure: Friedel pairs were merged.
Primary atom site location: structure-invariant direct methods
Crystal data top
C31H48O3V = 2658.2 (1) Å3
Mr = 468.69Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.0298 (2) ŵ = 0.07 mm−1
b = 8.4775 (2) ÅT = 100 K
c = 39.0492 (7) Å0.25 × 0.15 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer		3188 reflections with I > 2σ(I)
18588 measured reflectionsRint = 0.041
3500 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.27 e Å−3
S = 1.05Δρmin = −0.18 e Å−3
3500 reflectionsAbsolute structure: Friedel pairs were merged.
315 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.36083 (18)−0.12139 (18)0.89475 (4)0.0258 (3)
O21.10487 (18)−0.22743 (17)0.89389 (4)0.0248 (3)
O30.49772 (19)0.76407 (17)0.78616 (4)0.0240 (3)
C11.4023 (3)−0.2216 (3)0.86615 (6)0.0379 (6)
H1A1.5215−0.21270.86120.057*
H1B1.3381−0.18890.84600.057*
H1C1.3753−0.33130.87180.057*
C21.2031 (2)−0.1362 (2)0.90610 (5)0.0165 (4)
C31.1709 (2)−0.0328 (2)0.93751 (4)0.0140 (4)
C41.2429 (2)−0.1294 (2)0.96749 (4)0.0183 (4)
H4A1.2020−0.23930.96590.022*
H4B1.3659−0.13190.96560.022*
C51.1951 (2)−0.0617 (2)1.00218 (5)0.0182 (4)
H5A1.2394−0.13041.02060.022*
H5B1.24540.04421.00490.022*
C61.0070 (2)−0.0492 (2)1.00570 (4)0.0162 (4)
H60.9602−0.15751.00260.019*
C70.9619 (3)0.0053 (3)1.04214 (5)0.0223 (4)
H7A1.0134−0.06571.05890.034*
H7B0.84070.00341.04500.034*
H7C1.00300.11291.04580.034*
C80.9321 (2)0.0558 (2)0.97752 (4)0.0153 (4)
H80.97830.16470.98020.018*
C90.7425 (2)0.0651 (3)0.98027 (5)0.0200 (4)
H9A0.71170.10851.00260.030*
H9B0.6950−0.04080.97780.030*
H9C0.69910.13350.96210.030*
C100.9816 (2)−0.0071 (2)0.94123 (4)0.0137 (4)
H100.9292−0.11360.93900.016*
C110.9163 (2)0.0908 (2)0.91111 (4)0.0134 (4)
C121.0129 (2)0.2364 (2)0.89869 (4)0.0130 (3)
C130.9586 (2)0.3774 (2)0.92132 (4)0.0159 (4)
H13A0.99660.36030.94490.024*
H13B0.83690.38640.92100.024*
H13C1.00800.47480.91240.024*
C141.2042 (2)0.2181 (2)0.90294 (4)0.0147 (4)
H14A1.24880.16350.88250.018*
H14B1.25480.32450.90370.018*
C151.2586 (2)0.1272 (2)0.93475 (4)0.0147 (4)
H15A1.23330.19070.95540.018*
H15B1.38060.11050.93390.018*
C160.7737 (2)0.0499 (2)0.89632 (5)0.0166 (4)
H160.7174−0.03900.90560.020*
C170.6929 (2)0.1307 (2)0.86633 (5)0.0185 (4)
H17A0.57660.15720.87250.022*
H17B0.68920.05620.84680.022*
C180.7820 (2)0.2819 (2)0.85481 (4)0.0132 (4)
H180.74940.36370.87200.016*
C190.9742 (2)0.2627 (2)0.85904 (4)0.0128 (3)
C201.0371 (2)0.1194 (2)0.83823 (5)0.0162 (4)
H20A0.99270.12480.81490.024*
H20B0.99940.02180.84920.024*
H20C1.15910.12090.83740.024*
C211.0636 (2)0.4126 (2)0.84642 (5)0.0143 (4)
H21A1.04700.49760.86350.017*
H21B1.18460.39100.84500.017*
C221.0031 (2)0.4709 (2)0.81144 (4)0.0147 (4)
H22A1.06300.56880.80510.018*
H22B1.02660.39030.79380.018*
C230.8158 (2)0.5030 (2)0.81302 (4)0.0132 (4)
H230.80020.56500.83460.016*
C240.7187 (2)0.3472 (2)0.81932 (4)0.0126 (4)
C250.7322 (2)0.2282 (2)0.78945 (5)0.0169 (4)
H25A0.65120.25560.77170.025*
H25B0.70910.12160.79790.025*
H25C0.84480.23180.77980.025*
C260.5327 (2)0.3877 (2)0.82365 (5)0.0162 (4)
H26A0.46800.28850.82520.019*
H26B0.51730.44570.84540.019*
C270.4635 (2)0.4882 (2)0.79402 (5)0.0194 (4)
H27A0.46280.42420.77280.023*
H27B0.34700.51800.79920.023*
C280.5640 (2)0.6353 (2)0.78803 (4)0.0161 (4)
C290.7522 (2)0.6149 (2)0.78399 (5)0.0154 (4)
C300.8357 (3)0.7772 (2)0.78758 (5)0.0221 (4)
H30A0.78330.85180.77170.033*
H30B0.95450.76800.78220.033*
H30C0.82250.81520.81110.033*
C310.7843 (3)0.5552 (2)0.74714 (5)0.0191 (4)
H31A0.75150.63680.73070.029*
H31B0.71880.45950.74300.029*
H31C0.90300.53140.74430.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0229 (8)0.0265 (8)0.0280 (7)−0.0023 (7)0.0098 (6)−0.0121 (7)
O20.0256 (8)0.0206 (7)0.0282 (7)−0.0029 (7)0.0032 (6)−0.0095 (6)
O30.0262 (8)0.0243 (7)0.0214 (7)0.0104 (7)0.0007 (6)0.0034 (6)
C10.0362 (13)0.0389 (14)0.0386 (13)−0.0035 (12)0.0176 (11)−0.0223 (12)
C20.0203 (9)0.0127 (9)0.0165 (8)0.0014 (8)0.0017 (7)0.0016 (7)
C30.0172 (9)0.0124 (9)0.0125 (8)0.0009 (7)0.0009 (7)0.0006 (7)
C40.0213 (10)0.0170 (9)0.0165 (9)0.0022 (8)0.0003 (7)0.0019 (8)
C50.0217 (10)0.0191 (9)0.0138 (8)0.0024 (8)−0.0033 (7)0.0044 (7)
C60.0215 (10)0.0140 (8)0.0130 (8)0.0003 (8)0.0010 (7)0.0010 (7)
C70.0292 (11)0.0238 (10)0.0139 (9)−0.0002 (9)0.0005 (8)0.0007 (8)
C80.0185 (10)0.0139 (9)0.0135 (8)−0.0003 (8)0.0018 (7)0.0005 (7)
C90.0200 (10)0.0241 (10)0.0158 (9)−0.0001 (8)0.0033 (7)−0.0005 (8)
C100.0155 (9)0.0126 (8)0.0130 (8)−0.0005 (7)0.0007 (7)0.0007 (7)
C110.0154 (9)0.0124 (9)0.0123 (8)0.0009 (7)0.0033 (7)0.0001 (7)
C120.0145 (8)0.0115 (8)0.0130 (8)−0.0004 (7)−0.0003 (7)0.0003 (7)
C130.0208 (10)0.0136 (9)0.0134 (8)−0.0010 (8)−0.0003 (7)−0.0014 (7)
C140.0133 (9)0.0169 (9)0.0140 (8)−0.0026 (8)0.0005 (7)0.0020 (7)
C150.0145 (9)0.0152 (9)0.0144 (8)−0.0008 (8)−0.0011 (7)−0.0006 (7)
C160.0201 (9)0.0143 (9)0.0154 (8)−0.0023 (8)0.0021 (7)0.0033 (7)
C170.0156 (9)0.0225 (10)0.0172 (9)−0.0046 (8)−0.0018 (7)0.0043 (8)
C180.0127 (8)0.0150 (9)0.0119 (8)−0.0002 (7)0.0003 (6)0.0004 (7)
C190.0110 (8)0.0143 (8)0.0131 (8)−0.0006 (7)0.0008 (6)0.0005 (7)
C200.0162 (9)0.0180 (9)0.0142 (8)0.0025 (8)0.0001 (7)−0.0026 (7)
C210.0109 (9)0.0165 (9)0.0153 (8)−0.0017 (7)−0.0006 (7)0.0034 (7)
C220.0122 (9)0.0178 (9)0.0142 (8)−0.0010 (8)0.0013 (7)0.0028 (7)
C230.0131 (9)0.0145 (9)0.0119 (8)0.0005 (7)0.0000 (6)−0.0005 (7)
C240.0110 (8)0.0149 (9)0.0117 (8)0.0008 (7)0.0003 (6)0.0007 (7)
C250.0185 (9)0.0172 (9)0.0151 (8)0.0004 (8)−0.0016 (7)−0.0007 (7)
C260.0127 (9)0.0210 (10)0.0150 (8)−0.0006 (8)0.0004 (7)0.0023 (8)
C270.0124 (9)0.0268 (11)0.0191 (9)0.0028 (8)−0.0007 (7)0.0021 (8)
C280.0181 (9)0.0228 (10)0.0074 (7)0.0048 (8)−0.0010 (6)0.0000 (7)
C290.0168 (9)0.0138 (9)0.0155 (8)0.0009 (8)−0.0009 (7)0.0023 (7)
C300.0251 (10)0.0150 (9)0.0262 (10)−0.0010 (9)−0.0042 (8)0.0030 (8)
C310.0222 (10)0.0210 (10)0.0140 (8)0.0011 (9)0.0020 (7)0.0031 (8)
Geometric parameters (Å, °) top
O1—C21.348 (2)C15—H15B0.9900
O1—C11.442 (2)C16—C171.504 (3)
O2—C21.203 (2)C16—H160.9500
O3—C281.217 (2)C17—C181.535 (3)
C1—H1A0.9800C17—H17A0.9900
C1—H1B0.9800C17—H17B0.9900
C1—H1C0.9800C18—C191.560 (2)
C2—C31.529 (3)C18—C241.577 (2)
C3—C151.532 (3)C18—H181.0000
C3—C41.542 (3)C19—C211.540 (3)
C3—C101.543 (3)C19—C201.546 (3)
C4—C51.521 (3)C20—H20A0.9800
C4—H4A0.9900C20—H20B0.9800
C4—H4B0.9900C20—H20C0.9800
C5—C61.520 (3)C21—C221.532 (2)
C5—H5A0.9900C21—H21A0.9900
C5—H5B0.9900C21—H21B0.9900
C6—C81.538 (3)C22—C231.530 (3)
C6—C71.539 (2)C22—H22A0.9900
C6—H61.0000C22—H22B0.9900
C7—H7A0.9800C23—C241.554 (3)
C7—H7B0.9800C23—C291.563 (3)
C7—H7C0.9800C23—H231.0000
C8—C91.529 (3)C24—C261.542 (3)
C8—C101.565 (2)C24—C251.546 (2)
C8—H81.0000C25—H25A0.9800
C9—H9A0.9800C25—H25B0.9800
C9—H9B0.9800C25—H25C0.9800
C9—H9C0.9800C26—C271.540 (3)
C10—C111.532 (2)C26—H26A0.9900
C10—H101.0000C26—H26B0.9900
C11—C161.328 (3)C27—C281.504 (3)
C11—C121.536 (3)C27—H27A0.9900
C12—C131.550 (3)C27—H27B0.9900
C12—C141.553 (2)C28—C291.529 (3)
C12—C191.595 (2)C29—C301.537 (3)
C13—H13A0.9800C29—C311.547 (3)
C13—H13B0.9800C30—H30A0.9800
C13—H13C0.9800C30—H30B0.9800
C14—C151.525 (2)C30—H30C0.9800
C14—H14A0.9900C31—H31A0.9800
C14—H14B0.9900C31—H31B0.9800
C15—H15A0.9900C31—H31C0.9800
C2—O1—C1114.64 (17)C16—C17—C18114.04 (16)
O1—C1—H1A109.5C16—C17—H17A108.7
O1—C1—H1B109.5C18—C17—H17A108.7
H1A—C1—H1B109.5C16—C17—H17B108.7
O1—C1—H1C109.5C18—C17—H17B108.7
H1A—C1—H1C109.5H17A—C17—H17B107.6
H1B—C1—H1C109.5C17—C18—C19110.08 (15)
O2—C2—O1123.04 (18)C17—C18—C24113.61 (15)
O2—C2—C3125.15 (18)C19—C18—C24116.65 (14)
O1—C2—C3111.67 (16)C17—C18—H18105.1
C2—C3—C15111.93 (15)C19—C18—H18105.1
C2—C3—C4103.95 (15)C24—C18—H18105.1
C15—C3—C4110.59 (15)C21—C19—C20109.13 (14)
C2—C3—C10108.83 (15)C21—C19—C18109.96 (15)
C15—C3—C10109.55 (15)C20—C19—C18110.44 (15)
C4—C3—C10111.90 (15)C21—C19—C12109.60 (14)
C5—C4—C3112.40 (15)C20—C19—C12109.65 (14)
C5—C4—H4A109.1C18—C19—C12108.04 (13)
C3—C4—H4A109.1C19—C20—H20A109.5
C5—C4—H4B109.1C19—C20—H20B109.5
C3—C4—H4B109.1H20A—C20—H20B109.5
H4A—C4—H4B107.9C19—C20—H20C109.5
C6—C5—C4110.98 (16)H20A—C20—H20C109.5
C6—C5—H5A109.4H20B—C20—H20C109.5
C4—C5—H5A109.4C22—C21—C19113.81 (15)
C6—C5—H5B109.4C22—C21—H21A108.8
C4—C5—H5B109.4C19—C21—H21A108.8
H5A—C5—H5B108.0C22—C21—H21B108.8
C5—C6—C8111.37 (15)C19—C21—H21B108.8
C5—C6—C7109.76 (16)H21A—C21—H21B107.7
C8—C6—C7113.34 (16)C23—C22—C21109.47 (15)
C5—C6—H6107.4C23—C22—H22A109.8
C8—C6—H6107.4C21—C22—H22A109.8
C7—C6—H6107.4C23—C22—H22B109.8
C6—C7—H7A109.5C21—C22—H22B109.8
C6—C7—H7B109.5H22A—C22—H22B108.2
H7A—C7—H7B109.5C22—C23—C24110.40 (15)
C6—C7—H7C109.5C22—C23—C29113.55 (15)
H7A—C7—H7C109.5C24—C23—C29117.82 (15)
H7B—C7—H7C109.5C22—C23—H23104.5
C9—C8—C6111.65 (16)C24—C23—H23104.5
C9—C8—C10109.50 (15)C29—C23—H23104.5
C6—C8—C10110.56 (15)C26—C24—C25107.21 (15)
C9—C8—H8108.3C26—C24—C23108.31 (15)
C6—C8—H8108.3C25—C24—C23113.59 (14)
C10—C8—H8108.3C26—C24—C18107.13 (14)
C8—C9—H9A109.5C25—C24—C18114.27 (15)
C8—C9—H9B109.5C23—C24—C18106.02 (14)
H9A—C9—H9B109.5C24—C25—H25A109.5
C8—C9—H9C109.5C24—C25—H25B109.5
H9A—C9—H9C109.5H25A—C25—H25B109.5
H9B—C9—H9C109.5C24—C25—H25C109.5
C11—C10—C3109.96 (15)H25A—C25—H25C109.5
C11—C10—C8115.04 (15)H25B—C25—H25C109.5
C3—C10—C8112.55 (15)C27—C26—C24112.97 (15)
C11—C10—H10106.2C27—C26—H26A109.0
C3—C10—H10106.2C24—C26—H26A109.0
C8—C10—H10106.2C27—C26—H26B109.0
C16—C11—C10119.15 (17)C24—C26—H26B109.0
C16—C11—C12120.51 (17)H26A—C26—H26B107.8
C10—C11—C12120.32 (16)C28—C27—C26112.43 (16)
C11—C12—C13107.33 (14)C28—C27—H27A109.1
C11—C12—C14112.66 (15)C26—C27—H27A109.1
C13—C12—C14107.13 (15)C28—C27—H27B109.1
C11—C12—C19108.71 (14)C26—C27—H27B109.1
C13—C12—C19113.01 (15)H27A—C27—H27B107.8
C14—C12—C19108.08 (14)O3—C28—C27121.22 (17)
C12—C13—H13A109.5O3—C28—C29121.86 (19)
C12—C13—H13B109.5C27—C28—C29116.92 (17)
H13A—C13—H13B109.5C28—C29—C30108.67 (16)
C12—C13—H13C109.5C28—C29—C31107.33 (15)
H13A—C13—H13C109.5C30—C29—C31107.77 (16)
H13B—C13—H13C109.5C28—C29—C23108.44 (15)
C15—C14—C12114.89 (15)C30—C29—C23109.54 (15)
C15—C14—H14A108.5C31—C29—C23114.94 (15)
C12—C14—H14A108.5C29—C30—H30A109.5
C15—C14—H14B108.5C29—C30—H30B109.5
C12—C14—H14B108.5H30A—C30—H30B109.5
H14A—C14—H14B107.5C29—C30—H30C109.5
C14—C15—C3111.87 (15)H30A—C30—H30C109.5
C14—C15—H15A109.2H30B—C30—H30C109.5
C3—C15—H15A109.2C29—C31—H31A109.5
C14—C15—H15B109.2C29—C31—H31B109.5
C3—C15—H15B109.2H31A—C31—H31B109.5
H15A—C15—H15B107.9C29—C31—H31C109.5
C11—C16—C17126.25 (18)H31A—C31—H31C109.5
C11—C16—H16116.9H31B—C31—H31C109.5
C17—C16—H16116.9
C1—O1—C2—O21.3 (3)C24—C18—C19—C2146.9 (2)
C1—O1—C2—C3177.10 (18)C17—C18—C19—C2057.77 (19)
O2—C2—C3—C15−145.83 (19)C24—C18—C19—C20−73.6 (2)
O1—C2—C3—C1538.5 (2)C17—C18—C19—C12−62.16 (18)
O2—C2—C3—C494.8 (2)C24—C18—C19—C12166.51 (15)
O1—C2—C3—C4−80.92 (19)C11—C12—C19—C21177.46 (14)
O2—C2—C3—C10−24.6 (3)C13—C12—C19—C2158.42 (19)
O1—C2—C3—C10159.69 (16)C14—C12—C19—C21−59.95 (18)
C2—C3—C4—C5−169.25 (16)C11—C12—C19—C20−62.76 (18)
C15—C3—C4—C570.5 (2)C13—C12—C19—C20178.20 (15)
C10—C3—C4—C5−52.0 (2)C14—C12—C19—C2059.82 (19)
C3—C4—C5—C656.4 (2)C11—C12—C19—C1857.66 (18)
C4—C5—C6—C8−58.8 (2)C13—C12—C19—C18−61.39 (19)
C4—C5—C6—C7174.87 (15)C14—C12—C19—C18−179.76 (15)
C5—C6—C8—C9178.32 (17)C20—C19—C21—C2273.64 (19)
C7—C6—C8—C9−57.3 (2)C18—C19—C21—C22−47.6 (2)
C5—C6—C8—C1056.1 (2)C12—C19—C21—C22−166.27 (15)
C7—C6—C8—C10−179.51 (16)C19—C21—C22—C2357.9 (2)
C2—C3—C10—C11−66.30 (19)C21—C22—C23—C24−65.05 (18)
C15—C3—C10—C1156.37 (19)C21—C22—C23—C29160.11 (15)
C4—C3—C10—C11179.39 (15)C22—C23—C24—C26175.43 (14)
C2—C3—C10—C8164.02 (15)C29—C23—C24—C26−51.87 (19)
C15—C3—C10—C8−73.31 (18)C22—C23—C24—C25−65.58 (19)
C4—C3—C10—C849.7 (2)C29—C23—C24—C2567.1 (2)
C9—C8—C10—C1157.7 (2)C22—C23—C24—C1860.73 (17)
C6—C8—C10—C11−178.85 (16)C29—C23—C24—C18−166.57 (15)
C9—C8—C10—C3−175.27 (16)C17—C18—C24—C2661.65 (19)
C6—C8—C10—C3−51.8 (2)C19—C18—C24—C26−168.67 (16)
C3—C10—C11—C16137.50 (18)C17—C18—C24—C25−56.9 (2)
C8—C10—C11—C16−94.2 (2)C19—C18—C24—C2572.7 (2)
C3—C10—C11—C12−43.7 (2)C17—C18—C24—C23177.16 (15)
C8—C10—C11—C1284.6 (2)C19—C18—C24—C23−53.2 (2)
C16—C11—C12—C1393.9 (2)C25—C24—C26—C27−70.3 (2)
C10—C11—C12—C13−84.86 (19)C23—C24—C26—C2752.61 (19)
C16—C11—C12—C14−148.42 (17)C18—C24—C26—C27166.58 (15)
C10—C11—C12—C1432.8 (2)C24—C26—C27—C28−53.9 (2)
C16—C11—C12—C19−28.6 (2)C26—C27—C28—O3−129.36 (18)
C10—C11—C12—C19152.60 (15)C26—C27—C28—C2951.4 (2)
C11—C12—C14—C15−35.7 (2)O3—C28—C29—C3015.4 (2)
C13—C12—C14—C1582.15 (19)C27—C28—C29—C30−165.39 (16)
C19—C12—C14—C15−155.78 (15)O3—C28—C29—C31−100.9 (2)
C12—C14—C15—C352.3 (2)C27—C28—C29—C3178.33 (19)
C2—C3—C15—C1458.1 (2)O3—C28—C29—C23134.38 (18)
C4—C3—C15—C14173.52 (15)C27—C28—C29—C23−46.4 (2)
C10—C3—C15—C14−62.68 (19)C22—C23—C29—C28179.09 (15)
C10—C11—C16—C17−179.08 (17)C24—C23—C29—C2847.8 (2)
C12—C11—C16—C172.2 (3)C22—C23—C29—C30−62.5 (2)
C11—C16—C17—C18−5.3 (3)C24—C23—C29—C30166.24 (16)
C16—C17—C18—C1935.7 (2)C22—C23—C29—C3159.0 (2)
C16—C17—C18—C24168.65 (15)C24—C23—C29—C31−72.3 (2)
C17—C18—C19—C21178.27 (14)
Acknowledgements top

We thank the University of Malaya for supporting this study.

references
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