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Acta Cryst. (2009). E65, o1026    [ doi:10.1107/S160053680901188X ]

(20R,24R,25S)-3[alpha],7[alpha],12[alpha],27-Tetraacetoxy-24,26-epoxy-5[beta]-cholestane

K. A. Ketuly, A. H. A. Hadi and S. W. Ng

Abstract top

In the title anhydroscymnol tetraacetate, C35H54O9, the fused chair conformation of the cyclohexane A/B ring junction is cis with a 5[beta]-H configuration. The compound has a trimethylene oxide ring at position 24,26 and four acetate groups at the 3[alpha],7[alpha],12[alpha],27 positions.

Related literature top

For the synthesis from shark bile sterol sodium scymnol sulfate, see: Cross (1961). For the assignment of the absolute configuration of the carbon at the 20-position in (20S)-6β-methoxy-20-(p-toluenesulfoxymethyl)-3α,5-cyclo-5α-pregnane see: Ketuly et al. (1997). For the crystal structure of the unacetylated anhydroscymnol, see: Ishida et al. (1991, 1994); other studies have not mentioned the configuration at C20.

Experimental top

Anhydroscymnol (1 mmol) was reacted with acetic anhydride (1.3 mmol) in dry pyridine at 343 K for 2 hours. Water was added to the mixture, and the product extracted with ethyl acetate. The solvent was removed and the product was fractionated over a silica gel column and eluted with hexane:ethyl acetate (3:1 v/v). The semicrystalline fraction was recrystallized with hexane:ethyl acetate; m.p. 423–425 K [Lit. 420–423 K (Cross, 1961)].

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C).

The absolute configuration of the carbon atom at position 20 is based on the absolute configuration of (20S)-6β-methoxy-20-(p-toluenesulfoxymethyl)-3α,5-cyclo-5α-pregnane (Ketuly et al., 1997).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (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. Thermal ellipsoid plot (Barbour, 2001) of C35H54O9 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
(20R,24R,25S)-3α,7α,12α,27-Tetraacetoxy-24,26-epoxy- 5β-cholestane top
Crystal data top
C35H54O9F(000) = 1344
Mr = 618.78Dx = 1.244 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9970 reflections
a = 10.9474 (2) Åθ = 2.5–28.1°
b = 14.7638 (2) ŵ = 0.09 mm−1
c = 20.4477 (3) ÅT = 100 K
V = 3304.86 (9) Å3Block, colorless
Z = 40.35 × 0.30 × 0.25 mm
Data collection top
Bruker SMART APEX
diffractometer		4212 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 28.3°, θmin = 1.7°
ω scansh = −14→14
28923 measured reflectionsk = −19→19
4552 independent reflectionsl = −27→27
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0562P)2 + 0.4501P]
where P = (Fo2 + 2Fc2)/3
4552 reflections(Δ/σ)max = 0.001
404 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C35H54O9V = 3304.86 (9) Å3
Mr = 618.78Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.9474 (2) ŵ = 0.09 mm−1
b = 14.7638 (2) ÅT = 100 K
c = 20.4477 (3) Å0.35 × 0.30 × 0.25 mm
Data collection top
Bruker SMART APEX
diffractometer		4212 reflections with I > 2σ(I)
28923 measured reflectionsRint = 0.031
4552 independent reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.085Δρmax = 0.29 e Å−3
S = 1.00Δρmin = −0.16 e Å−3
4552 reflectionsAbsolute structure: ?
404 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
O10.68083 (10)−0.09988 (7)0.82696 (6)0.0191 (2)
O20.53071 (12)−0.18393 (9)0.87116 (7)0.0294 (3)
O30.70747 (10)0.17227 (7)0.96918 (5)0.0168 (2)
O40.65553 (13)0.15801 (9)1.07531 (6)0.0288 (3)
O50.91968 (10)0.28801 (8)0.82837 (6)0.0192 (2)
O61.00233 (15)0.27411 (10)0.72826 (7)0.0399 (4)
O71.13334 (12)0.85069 (8)0.92430 (7)0.0295 (3)
O81.19343 (14)0.96010 (11)0.85535 (8)0.0431 (4)
O91.29555 (10)0.62411 (8)0.99315 (6)0.0209 (2)
C10.59639 (14)−0.02458 (10)0.81801 (8)0.0179 (3)
H10.5146−0.04820.80440.021*
C20.58408 (15)0.02767 (10)0.88158 (8)0.0178 (3)
H2A0.66600.04730.89640.021*
H2B0.5495−0.01260.91560.021*
C30.50121 (14)0.11141 (10)0.87363 (7)0.0168 (3)
H30.41780.08840.86270.020*
C40.54085 (14)0.17409 (10)0.81621 (8)0.0165 (3)
C50.56181 (15)0.11502 (11)0.75483 (8)0.0201 (3)
H5A0.48180.09170.73980.024*
H5B0.59500.15390.71960.024*
C60.64795 (16)0.03487 (11)0.76451 (8)0.0194 (3)
H6A0.65520.00000.72340.023*
H6B0.73020.05670.77700.023*
C70.48981 (14)0.16309 (10)0.93883 (8)0.0178 (3)
H7A0.41440.20010.93760.021*
H7B0.48060.11840.97460.021*
C80.59733 (14)0.22508 (10)0.95498 (7)0.0155 (3)
H80.57630.26330.99380.019*
C90.63102 (14)0.28605 (10)0.89768 (7)0.0143 (3)
H90.55800.32420.88740.017*
C100.65823 (14)0.22709 (10)0.83682 (7)0.0136 (3)
H100.71910.18060.85100.016*
C110.43540 (15)0.23919 (12)0.79937 (9)0.0223 (3)
H11A0.36740.20480.78060.033*
H11B0.46380.28420.76760.033*
H11C0.40800.27000.83920.033*
C120.71774 (15)0.27970 (11)0.78018 (7)0.0172 (3)
H12A0.75070.23580.74810.021*
H12B0.65400.31580.75780.021*
C130.82089 (14)0.34333 (10)0.80156 (7)0.0161 (3)
H130.85120.37880.76320.019*
C140.77911 (13)0.40776 (10)0.85570 (7)0.0136 (3)
C150.73613 (13)0.34986 (10)0.91417 (7)0.0134 (3)
H150.80680.31130.92770.016*
C160.67683 (15)0.46758 (11)0.82692 (8)0.0190 (3)
H16A0.60340.43080.82000.029*
H16B0.70380.49300.78510.029*
H16C0.65830.51690.85740.029*
C170.71512 (15)0.41932 (10)0.96898 (8)0.0172 (3)
H17A0.73080.39211.01240.021*
H17B0.63040.44280.96790.021*
C180.80838 (14)0.49564 (10)0.95403 (7)0.0163 (3)
H18A0.86690.50220.99060.020*
H18B0.76560.55410.94780.020*
C190.87656 (14)0.46804 (10)0.89041 (7)0.0143 (3)
H190.94650.42820.90310.017*
C200.92883 (14)0.54939 (10)0.85230 (8)0.0160 (3)
H200.85790.58260.83300.019*
C211.01046 (16)0.51931 (11)0.79530 (8)0.0207 (3)
H21A1.05520.57170.77820.031*
H21B0.95970.49340.76060.031*
H21C1.06870.47360.81070.031*
C220.99790 (15)0.61701 (10)0.89648 (8)0.0172 (3)
H22A1.02010.67060.86990.021*
H22B0.94150.63780.93120.021*
C231.11407 (15)0.58050 (10)0.92896 (8)0.0179 (3)
H23A1.09200.53450.96220.021*
H23B1.16630.55100.89570.021*
C241.18393 (14)0.65683 (10)0.96117 (8)0.0168 (3)
H241.13140.69280.99160.020*
C251.25942 (15)0.71781 (11)0.91536 (8)0.0190 (3)
H251.24660.70440.86790.023*
C261.25669 (16)0.81756 (11)0.93112 (11)0.0277 (4)
H26A1.28560.82760.97640.033*
H26B1.31150.85080.90100.033*
C271.37105 (16)0.66966 (12)0.94467 (9)0.0243 (4)
H27A1.41130.62750.91380.029*
H27B1.43140.71180.96410.029*
C280.63620 (16)−0.17487 (11)0.85596 (8)0.0207 (3)
C290.73426 (17)−0.24348 (12)0.86679 (9)0.0252 (4)
H29A0.6974−0.30360.87180.038*
H29B0.7800−0.22810.90640.038*
H29C0.7898−0.24390.82920.038*
C300.72559 (15)0.14408 (10)1.03085 (8)0.0185 (3)
C310.84298 (16)0.09206 (11)1.03599 (9)0.0231 (3)
H31A0.86740.08791.08200.035*
H31B0.90680.12331.01110.035*
H31C0.83130.03101.01820.035*
C321.00340 (17)0.25635 (12)0.78586 (10)0.0270 (4)
C331.09408 (17)0.19690 (14)0.81905 (12)0.0389 (5)
H33A1.12690.15320.78760.058*
H33B1.05420.16440.85500.058*
H33C1.16080.23400.83650.058*
C341.11389 (17)0.92218 (11)0.88489 (8)0.0229 (3)
C350.98074 (18)0.94542 (13)0.88180 (10)0.0304 (4)
H35A0.97131.01080.87530.046*
H35B0.94110.92760.92280.046*
H35C0.94270.91300.84530.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0182 (5)0.0162 (5)0.0229 (5)0.0002 (4)0.0016 (4)−0.0014 (4)
O20.0229 (6)0.0231 (6)0.0421 (8)0.0000 (5)0.0072 (6)0.0067 (6)
O30.0157 (5)0.0189 (5)0.0157 (5)0.0019 (4)0.0015 (4)0.0019 (4)
O40.0374 (7)0.0318 (7)0.0172 (6)0.0029 (6)0.0043 (5)0.0002 (5)
O50.0146 (5)0.0204 (5)0.0225 (6)−0.0001 (4)0.0033 (4)−0.0054 (5)
O60.0486 (9)0.0355 (7)0.0356 (8)−0.0047 (7)0.0239 (7)−0.0119 (6)
O70.0256 (6)0.0192 (6)0.0438 (8)0.0011 (5)0.0051 (6)0.0090 (6)
O80.0308 (7)0.0471 (9)0.0515 (9)−0.0036 (7)0.0047 (7)0.0246 (8)
O90.0181 (5)0.0223 (6)0.0224 (6)−0.0028 (5)−0.0049 (5)0.0037 (5)
C10.0170 (7)0.0155 (7)0.0212 (8)−0.0003 (6)−0.0003 (6)−0.0007 (6)
C20.0194 (7)0.0147 (7)0.0194 (7)−0.0011 (6)0.0019 (6)0.0005 (6)
C30.0133 (6)0.0171 (7)0.0201 (7)−0.0026 (6)0.0006 (6)0.0001 (6)
C40.0137 (7)0.0162 (7)0.0195 (7)−0.0028 (6)−0.0028 (6)0.0007 (6)
C50.0227 (8)0.0196 (7)0.0179 (7)−0.0056 (7)−0.0042 (6)−0.0007 (6)
C60.0225 (8)0.0197 (7)0.0159 (7)−0.0044 (6)0.0019 (6)−0.0025 (6)
C70.0142 (7)0.0170 (7)0.0223 (7)−0.0005 (6)0.0051 (6)−0.0004 (6)
C80.0143 (7)0.0158 (7)0.0164 (7)0.0018 (6)0.0027 (5)−0.0002 (6)
C90.0130 (6)0.0142 (6)0.0157 (7)−0.0011 (5)0.0009 (5)0.0004 (5)
C100.0130 (6)0.0135 (6)0.0144 (7)−0.0017 (5)−0.0010 (5)0.0000 (5)
C110.0172 (7)0.0217 (8)0.0280 (9)−0.0014 (6)−0.0069 (7)0.0027 (7)
C120.0200 (7)0.0180 (7)0.0136 (7)−0.0048 (6)−0.0008 (6)0.0005 (6)
C130.0173 (7)0.0162 (7)0.0147 (7)−0.0039 (6)0.0012 (6)−0.0011 (6)
C140.0132 (6)0.0129 (6)0.0148 (7)−0.0008 (6)−0.0019 (6)0.0005 (5)
C150.0124 (6)0.0136 (6)0.0141 (7)−0.0005 (5)0.0002 (5)−0.0001 (5)
C160.0168 (7)0.0167 (7)0.0236 (8)−0.0008 (6)−0.0058 (6)0.0027 (6)
C170.0172 (7)0.0171 (7)0.0174 (7)0.0000 (6)0.0013 (6)−0.0025 (6)
C180.0181 (7)0.0132 (6)0.0174 (7)0.0009 (6)−0.0009 (6)−0.0011 (5)
C190.0136 (6)0.0142 (6)0.0150 (7)0.0003 (5)−0.0015 (5)−0.0001 (5)
C200.0158 (7)0.0139 (6)0.0184 (7)−0.0009 (6)−0.0015 (6)0.0010 (6)
C210.0236 (8)0.0194 (7)0.0190 (7)−0.0059 (7)0.0027 (6)−0.0006 (6)
C220.0177 (7)0.0134 (6)0.0206 (7)0.0005 (6)−0.0026 (6)−0.0003 (6)
C230.0190 (7)0.0134 (7)0.0212 (8)−0.0024 (6)−0.0027 (6)0.0005 (6)
C240.0170 (7)0.0167 (7)0.0168 (7)−0.0012 (6)−0.0013 (6)0.0007 (6)
C250.0198 (7)0.0178 (7)0.0194 (7)−0.0028 (6)−0.0002 (6)0.0003 (6)
C260.0226 (8)0.0176 (8)0.0429 (10)−0.0041 (7)−0.0020 (8)0.0021 (7)
C270.0194 (8)0.0236 (8)0.0299 (9)0.0000 (7)0.0009 (7)0.0048 (7)
C280.0250 (8)0.0173 (7)0.0196 (8)0.0003 (6)0.0015 (6)−0.0029 (6)
C290.0260 (8)0.0217 (8)0.0279 (9)0.0047 (7)0.0022 (7)0.0001 (7)
C300.0229 (7)0.0158 (7)0.0167 (7)−0.0053 (6)−0.0031 (6)−0.0019 (6)
C310.0224 (8)0.0211 (8)0.0258 (8)−0.0013 (7)−0.0075 (7)0.0020 (7)
C320.0204 (8)0.0226 (8)0.0378 (10)−0.0089 (7)0.0113 (8)−0.0168 (7)
C330.0193 (8)0.0362 (10)0.0612 (14)0.0036 (8)0.0024 (9)−0.0261 (10)
C340.0307 (9)0.0185 (7)0.0196 (8)−0.0006 (7)0.0027 (7)−0.0002 (6)
C350.0300 (9)0.0277 (9)0.0335 (10)0.0056 (8)0.0092 (8)0.0070 (8)
Geometric parameters (Å, °) top
O1—C281.348 (2)C14—C191.560 (2)
O1—C11.4574 (19)C15—C171.536 (2)
O2—C281.203 (2)C15—H151.0000
O3—C301.3427 (19)C16—H16A0.9800
O3—C81.4650 (18)C16—H16B0.9800
O4—C301.207 (2)C16—H16C0.9800
O5—C321.347 (2)C17—C181.551 (2)
O5—C131.4619 (19)C17—H17A0.9900
O6—C321.207 (3)C17—H17B0.9900
O7—C341.345 (2)C18—C191.554 (2)
O7—C261.443 (2)C18—H18A0.9900
O8—C341.199 (2)C18—H18B0.9900
O9—C271.455 (2)C19—C201.542 (2)
O9—C241.4678 (19)C19—H191.0000
C1—C61.512 (2)C20—C211.534 (2)
C1—C21.518 (2)C20—C221.544 (2)
C1—H11.0000C20—H201.0000
C2—C31.542 (2)C21—H21A0.9800
C2—H2A0.9900C21—H21B0.9800
C2—H2B0.9900C21—H21C0.9800
C3—C71.541 (2)C22—C231.533 (2)
C3—C41.557 (2)C22—H22A0.9900
C3—H31.0000C22—H22B0.9900
C4—C111.541 (2)C23—C241.513 (2)
C4—C51.545 (2)C23—H23A0.9900
C4—C101.562 (2)C23—H23B0.9900
C5—C61.526 (2)C24—C251.540 (2)
C5—H5A0.9900C24—H241.0000
C5—H5B0.9900C25—C261.508 (2)
C6—H6A0.9900C25—C271.536 (2)
C6—H6B0.9900C25—H251.0000
C7—C81.527 (2)C26—H26A0.9900
C7—H7A0.9900C26—H26B0.9900
C7—H7B0.9900C27—H27A0.9900
C8—C91.523 (2)C27—H27B0.9900
C8—H81.0000C28—C291.492 (2)
C9—C151.525 (2)C29—H29A0.9800
C9—C101.548 (2)C29—H29B0.9800
C9—H91.0000C29—H29C0.9800
C10—C121.539 (2)C30—C311.501 (2)
C10—H101.0000C31—H31A0.9800
C11—H11A0.9800C31—H31B0.9800
C11—H11B0.9800C31—H31C0.9800
C11—H11C0.9800C32—C331.489 (3)
C12—C131.533 (2)C33—H33A0.9800
C12—H12A0.9900C33—H33B0.9800
C12—H12B0.9900C33—H33C0.9800
C13—C141.529 (2)C34—C351.499 (3)
C13—H131.0000C35—H35A0.9800
C14—C161.543 (2)C35—H35B0.9800
C14—C151.543 (2)C35—H35C0.9800
C28—O1—C1116.87 (12)C15—C17—H17A110.9
C30—O3—C8118.21 (12)C18—C17—H17A110.9
C32—O5—C13117.09 (14)C15—C17—H17B110.9
C34—O7—C26118.17 (14)C18—C17—H17B110.9
C27—O9—C2490.99 (11)H17A—C17—H17B109.0
O1—C1—C6107.27 (13)C17—C18—C19106.89 (12)
O1—C1—C2109.66 (13)C17—C18—H18A110.3
C6—C1—C2110.96 (12)C19—C18—H18A110.3
O1—C1—H1109.6C17—C18—H18B110.3
C6—C1—H1109.6C19—C18—H18B110.3
C2—C1—H1109.6H18A—C18—H18B108.6
C1—C2—C3111.69 (13)C20—C19—C18113.40 (12)
C1—C2—H2A109.3C20—C19—C14117.92 (12)
C3—C2—H2A109.3C18—C19—C14101.66 (12)
C1—C2—H2B109.3C20—C19—H19107.8
C3—C2—H2B109.3C18—C19—H19107.8
H2A—C2—H2B107.9C14—C19—H19107.8
C7—C3—C2110.69 (13)C21—C20—C19112.00 (12)
C7—C3—C4112.39 (12)C21—C20—C22110.27 (13)
C2—C3—C4113.09 (13)C19—C20—C22112.93 (12)
C7—C3—H3106.7C21—C20—H20107.1
C2—C3—H3106.7C19—C20—H20107.1
C4—C3—H3106.7C22—C20—H20107.1
C11—C4—C5106.37 (13)C20—C21—H21A109.5
C11—C4—C3109.29 (13)C20—C21—H21B109.5
C5—C4—C3108.57 (12)H21A—C21—H21B109.5
C11—C4—C10111.35 (12)C20—C21—H21C109.5
C5—C4—C10112.31 (13)H21A—C21—H21C109.5
C3—C4—C10108.87 (12)H21B—C21—H21C109.5
C6—C5—C4115.09 (13)C23—C22—C20115.62 (12)
C6—C5—H5A108.5C23—C22—H22A108.4
C4—C5—H5A108.5C20—C22—H22A108.4
C6—C5—H5B108.5C23—C22—H22B108.4
C4—C5—H5B108.5C20—C22—H22B108.4
H5A—C5—H5B107.5H22A—C22—H22B107.4
C1—C6—C5108.26 (13)C24—C23—C22110.25 (12)
C1—C6—H6A110.0C24—C23—H23A109.6
C5—C6—H6A110.0C22—C23—H23A109.6
C1—C6—H6B110.0C24—C23—H23B109.6
C5—C6—H6B110.0C22—C23—H23B109.6
H6A—C6—H6B108.4H23A—C23—H23B108.1
C8—C7—C3114.92 (13)O9—C24—C23111.69 (12)
C8—C7—H7A108.5O9—C24—C2590.95 (11)
C3—C7—H7A108.5C23—C24—C25116.24 (13)
C8—C7—H7B108.5O9—C24—H24112.1
C3—C7—H7B108.5C23—C24—H24112.1
H7A—C7—H7B107.5C25—C24—H24112.1
O3—C8—C9105.53 (11)C26—C25—C27112.61 (14)
O3—C8—C7110.99 (12)C26—C25—C24115.49 (14)
C9—C8—C7111.99 (13)C27—C25—C2485.35 (12)
O3—C8—H8109.4C26—C25—H25113.5
C9—C8—H8109.4C27—C25—H25113.5
C7—C8—H8109.4C24—C25—H25113.5
C8—C9—C15112.19 (12)O7—C26—C25109.20 (14)
C8—C9—C10109.44 (12)O7—C26—H26A109.8
C15—C9—C10112.34 (12)C25—C26—H26A109.8
C8—C9—H9107.5O7—C26—H26B109.8
C15—C9—H9107.5C25—C26—H26B109.8
C10—C9—H9107.5H26A—C26—H26B108.3
C12—C10—C9113.74 (12)O9—C27—C2591.60 (12)
C12—C10—C4113.44 (12)O9—C27—H27A113.4
C9—C10—C4109.90 (12)C25—C27—H27A113.4
C12—C10—H10106.4O9—C27—H27B113.4
C9—C10—H10106.4C25—C27—H27B113.4
C4—C10—H10106.4H27A—C27—H27B110.7
C4—C11—H11A109.5O2—C28—O1123.57 (16)
C4—C11—H11B109.5O2—C28—C29125.20 (16)
H11A—C11—H11B109.5O1—C28—C29111.23 (14)
C4—C11—H11C109.5C28—C29—H29A109.5
H11A—C11—H11C109.5C28—C29—H29B109.5
H11B—C11—H11C109.5H29A—C29—H29B109.5
C13—C12—C10113.99 (12)C28—C29—H29C109.5
C13—C12—H12A108.8H29A—C29—H29C109.5
C10—C12—H12A108.8H29B—C29—H29C109.5
C13—C12—H12B108.8O4—C30—O3124.10 (16)
C10—C12—H12B108.8O4—C30—C31125.36 (15)
H12A—C12—H12B107.7O3—C30—C31110.54 (14)
O5—C13—C14107.30 (12)C30—C31—H31A109.5
O5—C13—C12108.04 (12)C30—C31—H31B109.5
C14—C13—C12111.55 (13)H31A—C31—H31B109.5
O5—C13—H13110.0C30—C31—H31C109.5
C14—C13—H13110.0H31A—C31—H31C109.5
C12—C13—H13110.0H31B—C31—H31C109.5
C13—C14—C16107.28 (12)O6—C32—O5123.22 (19)
C13—C14—C15107.91 (11)O6—C32—C33125.41 (18)
C16—C14—C15113.03 (13)O5—C32—C33111.36 (17)
C13—C14—C19118.66 (12)C32—C33—H33A109.5
C16—C14—C19110.07 (12)C32—C33—H33B109.5
C15—C14—C1999.90 (11)H33A—C33—H33B109.5
C9—C15—C17117.44 (12)C32—C33—H33C109.5
C9—C15—C14113.63 (12)H33A—C33—H33C109.5
C17—C15—C14103.95 (12)H33B—C33—H33C109.5
C9—C15—H15107.1O8—C34—O7123.61 (17)
C17—C15—H15107.1O8—C34—C35125.34 (17)
C14—C15—H15107.1O7—C34—C35111.03 (15)
C14—C16—H16A109.5C34—C35—H35A109.5
C14—C16—H16B109.5C34—C35—H35B109.5
H16A—C16—H16B109.5H35A—C35—H35B109.5
C14—C16—H16C109.5C34—C35—H35C109.5
H16A—C16—H16C109.5H35A—C35—H35C109.5
H16B—C16—H16C109.5H35B—C35—H35C109.5
C15—C17—C18104.04 (12)
C28—O1—C1—C6−159.24 (13)C8—C9—C15—C17−62.70 (17)
C28—O1—C1—C280.16 (16)C10—C9—C15—C17173.51 (12)
O1—C1—C2—C3176.76 (12)C8—C9—C15—C14175.73 (12)
C6—C1—C2—C358.43 (17)C10—C9—C15—C1451.94 (16)
C1—C2—C3—C7179.80 (12)C13—C14—C15—C9−59.54 (16)
C1—C2—C3—C4−53.08 (17)C16—C14—C15—C958.92 (16)
C7—C3—C4—C11−69.76 (16)C19—C14—C15—C9175.84 (12)
C2—C3—C4—C11164.02 (13)C13—C14—C15—C17171.63 (12)
C7—C3—C4—C5174.61 (12)C16—C14—C15—C17−69.90 (15)
C2—C3—C4—C548.39 (16)C19—C14—C15—C1747.02 (14)
C7—C3—C4—C1052.06 (16)C9—C15—C17—C18−156.59 (13)
C2—C3—C4—C10−74.16 (15)C14—C15—C17—C18−30.13 (15)
C11—C4—C5—C6−170.10 (13)C15—C17—C18—C191.41 (16)
C3—C4—C5—C6−52.59 (17)C17—C18—C19—C20154.78 (12)
C10—C4—C5—C667.85 (17)C17—C18—C19—C1427.19 (14)
O1—C1—C6—C5−179.27 (12)C13—C14—C19—C2073.75 (17)
C2—C1—C6—C5−59.50 (17)C16—C14—C19—C20−50.32 (17)
C4—C5—C6—C158.59 (17)C15—C14—C19—C20−169.43 (12)
C2—C3—C7—C880.19 (16)C13—C14—C19—C18−161.62 (12)
C4—C3—C7—C8−47.32 (18)C16—C14—C19—C1874.31 (14)
C30—O3—C8—C9151.13 (13)C15—C14—C19—C18−44.81 (13)
C30—O3—C8—C7−87.34 (16)C18—C19—C20—C21171.99 (13)
C3—C7—C8—O3−68.55 (16)C14—C19—C20—C21−69.42 (17)
C3—C7—C8—C949.11 (17)C18—C19—C20—C2246.78 (17)
O3—C8—C9—C15−60.65 (15)C14—C19—C20—C22165.36 (13)
C7—C8—C9—C15178.47 (12)C21—C20—C22—C23−61.34 (17)
O3—C8—C9—C1064.75 (15)C19—C20—C22—C2364.81 (18)
C7—C8—C9—C10−56.13 (16)C20—C22—C23—C24170.42 (13)
C8—C9—C10—C12−168.46 (12)C27—O9—C24—C23110.70 (14)
C15—C9—C10—C12−43.15 (17)C27—O9—C24—C25−8.14 (12)
C8—C9—C10—C463.12 (15)C22—C23—C24—O9179.66 (12)
C15—C9—C10—C4−171.56 (12)C22—C23—C24—C25−77.87 (17)
C11—C4—C10—C12−68.69 (17)O9—C24—C25—C26−105.13 (15)
C5—C4—C10—C1250.48 (17)C23—C24—C25—C26140.01 (15)
C3—C4—C10—C12170.75 (12)O9—C24—C25—C277.74 (11)
C11—C4—C10—C959.89 (17)C23—C24—C25—C27−107.12 (15)
C5—C4—C10—C9179.06 (12)C34—O7—C26—C25−125.74 (16)
C3—C4—C10—C9−60.67 (15)C27—C25—C26—O7−158.84 (15)
C9—C10—C12—C1344.55 (18)C24—C25—C26—O7−63.0 (2)
C4—C10—C12—C13171.13 (13)C24—O9—C27—C258.17 (12)
C32—O5—C13—C14−152.07 (13)C26—C25—C27—O9107.91 (15)
C32—O5—C13—C1287.54 (15)C24—C25—C27—O9−7.81 (11)
C10—C12—C13—O564.29 (16)C1—O1—C28—O24.1 (2)
C10—C12—C13—C14−53.40 (17)C1—O1—C28—C29−175.51 (13)
O5—C13—C14—C16178.76 (11)C8—O3—C30—O41.5 (2)
C12—C13—C14—C16−63.10 (15)C8—O3—C30—C31−179.50 (12)
O5—C13—C14—C15−59.16 (15)C13—O5—C32—O62.6 (2)
C12—C13—C14—C1558.98 (16)C13—O5—C32—C33−176.65 (13)
O5—C13—C14—C1953.33 (16)C26—O7—C34—O8−0.3 (3)
C12—C13—C14—C19171.47 (12)C26—O7—C34—C35178.09 (16)
Acknowledgements top

We thank the University of Malaya for supporting this study.

references
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