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Acta Cryst. (2009). E65, o2114    [ doi:10.1107/S1600536809030657 ]

Methyl 3-acetoxy-3-dehydroxyursolate

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

Abstract top

Four of the five six-membered rings of the title pentacyclic triterpene, C33H52O4, adopt chair conformations; the fifth, which has a C=C double bond, adopts an approximate envelope conformation.

Related literature top

For the synthesis, see: Ma et al. (2005). The crystal structure of ursolic acid is known from its ethanol solvate; see: Simon et al. (1992). For methyl uroslate-3-bromoacetate, see: Stout & Stevens (1963). For methyl ursolate-3-p-bromobenzoate, see: Paton & Paul (1979).

Experimental top

The dried leaves of Primsatomorismalayana 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 acetic anhydride and pyridine 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: 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. The molecular structure of the methyl ursolate-3-acetate. Displacement ellipsoids are drawn at the 70% probability level, and hydrogen atoms are drawn as spheres of arbitrary radius.
Methyl 3-acetoxy-3-dehydroxyursolate top
Crystal data top
C33H52O4F(000) = 1128
Mr = 512.75Dx = 1.148 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9010 reflections
a = 6.8245 (1) Åθ = 2.4–28.2°
b = 13.4874 (2) ŵ = 0.07 mm−1
c = 32.2233 (5) ÅT = 100 K
V = 2965.99 (8) Å3Block, colorless
Z = 40.30 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		3612 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
graphiteθmax = 27.5°, θmin = 1.6°
ω scansh = −8→8
28565 measured reflectionsk = −17→17
3886 independent reflectionsl = −41→41
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0647P)2 + 0.329P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3886 reflectionsΔρmax = 0.35 e Å−3
343 parametersΔρmin = −0.18 e Å−3
0 restraintsAbsolute structure: Friedel pairs were merged.
Primary atom site location: structure-invariant direct methods
Crystal data top
C33H52O4V = 2965.99 (8) Å3
Mr = 512.75Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.8245 (1) ŵ = 0.07 mm−1
b = 13.4874 (2) ÅT = 100 K
c = 32.2233 (5) Å0.30 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		3612 reflections with I > 2σ(I)
28565 measured reflectionsRint = 0.034
3886 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.099Δρmax = 0.35 e Å−3
S = 1.07Δρmin = −0.18 e Å−3
3886 reflectionsAbsolute structure: Friedel pairs were merged.
343 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8683 (2)0.63811 (9)0.94880 (4)0.0230 (3)
O20.5731 (2)0.69609 (13)0.93041 (6)0.0470 (4)
O31.03757 (18)−0.18360 (9)0.86981 (4)0.0233 (3)
O41.20002 (18)−0.09494 (10)0.82218 (4)0.0260 (3)
C10.8406 (3)0.54575 (12)0.92596 (5)0.0186 (3)
H10.70880.54710.91240.022*
C20.8468 (3)0.45891 (13)0.95692 (5)0.0182 (3)
C30.8466 (2)0.36120 (12)0.93090 (5)0.0149 (3)
H30.71620.36050.91670.018*
C40.8493 (3)0.26628 (12)0.95708 (5)0.0180 (3)
H4A0.98400.25390.96720.022*
H4B0.76280.27470.98150.022*
C50.7799 (3)0.17749 (12)0.93146 (5)0.0170 (3)
H5A0.63990.18690.92450.020*
H5B0.79030.11690.94870.020*
C60.8959 (2)0.16124 (12)0.89087 (5)0.0130 (3)
C70.7757 (2)0.09206 (12)0.86003 (5)0.0132 (3)
C80.7354 (2)−0.00924 (12)0.88113 (5)0.0157 (3)
H8A0.8521−0.02810.89760.019*
H8B0.6246−0.00130.90070.019*
C90.6875 (2)−0.09377 (12)0.85118 (5)0.0161 (3)
H9A0.5591−0.08090.83790.019*
H9B0.6772−0.15660.86690.019*
C100.8445 (2)−0.10472 (12)0.81746 (5)0.0153 (3)
C110.8054 (3)−0.19544 (12)0.78927 (6)0.0194 (3)
H11A0.9208−0.20680.77130.023*
H11B0.7873−0.25500.80680.023*
C120.6244 (3)−0.18105 (13)0.76217 (6)0.0226 (4)
H12A0.5069−0.17690.78010.027*
H12B0.6088−0.23930.74380.027*
C130.6387 (3)−0.08737 (13)0.73579 (6)0.0236 (4)
H130.7532−0.09500.71670.028*
C140.6737 (3)0.00559 (12)0.76254 (5)0.0180 (3)
H140.55540.01660.78030.022*
C150.8546 (2)−0.00871 (12)0.79156 (5)0.0148 (3)
H150.9717−0.01510.77310.018*
C160.8921 (2)0.08048 (12)0.81955 (5)0.0130 (3)
C171.0181 (2)0.14961 (12)0.80750 (5)0.0158 (3)
H171.08860.13750.78260.019*
C181.0591 (3)0.24517 (12)0.82969 (5)0.0173 (3)
H18A1.03800.30090.81020.021*
H18B1.19860.24620.83810.021*
C190.9313 (2)0.26154 (11)0.86828 (5)0.0135 (3)
H190.80000.28080.85710.016*
C200.9982 (2)0.35270 (12)0.89520 (5)0.0144 (3)
C210.9818 (3)0.44612 (12)0.86787 (5)0.0189 (3)
H21A1.08730.44480.84680.023*
H21B0.85490.44470.85300.023*
C220.9963 (3)0.54291 (12)0.89246 (5)0.0206 (4)
H22A1.12770.54820.90530.025*
H22B0.97880.60000.87350.025*
C230.7261 (3)0.70689 (15)0.94762 (6)0.0280 (4)
C240.7851 (4)0.79780 (15)0.97118 (7)0.0381 (5)
H24A0.67190.84200.97400.057*
H24B0.88990.83220.95620.057*
H24C0.83220.77870.99880.057*
C251.0202 (3)0.46737 (14)0.98688 (6)0.0256 (4)
H25A0.99600.52131.00660.038*
H25B1.14010.48130.97120.038*
H25C1.03570.40491.00200.038*
C260.6580 (3)0.46347 (15)0.98272 (6)0.0260 (4)
H26A0.64760.52860.99600.039*
H26B0.66110.41171.00410.039*
H26C0.54470.45300.96460.039*
C271.0929 (2)0.11123 (12)0.90219 (5)0.0166 (3)
H27A1.17460.15810.91770.025*
H27B1.16100.09140.87670.025*
H27C1.06790.05250.91930.025*
C280.5736 (2)0.13716 (12)0.84835 (5)0.0167 (3)
H28A0.48770.08480.83770.025*
H28B0.59160.18790.82690.025*
H28C0.51420.16720.87300.025*
C291.0468 (3)−0.12439 (12)0.83603 (5)0.0173 (3)
C301.2249 (3)−0.20894 (15)0.88788 (7)0.0288 (4)
H30A1.2043−0.25120.91220.043*
H30B1.2930−0.14820.89630.043*
H30C1.3043−0.24450.86740.043*
C310.4540 (4)−0.07768 (16)0.70914 (8)0.0413 (6)
H31A0.4315−0.13980.69410.062*
H31B0.4711−0.02350.68920.062*
H31C0.3412−0.06360.72700.062*
C320.7024 (3)0.09685 (14)0.73502 (5)0.0263 (4)
H32A0.58350.10830.71870.039*
H32B0.81350.08580.71630.039*
H32C0.72850.15490.75250.039*
C331.2140 (3)0.34623 (13)0.91040 (6)0.0202 (4)
H33A1.26380.41310.91580.030*
H33B1.29450.31450.88900.030*
H33C1.21980.30700.93600.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0271 (7)0.0157 (6)0.0262 (6)0.0066 (5)−0.0052 (5)−0.0058 (5)
O20.0382 (9)0.0427 (9)0.0601 (10)0.0214 (8)−0.0182 (8)−0.0115 (8)
O30.0138 (6)0.0226 (6)0.0335 (7)−0.0004 (5)−0.0040 (5)0.0111 (5)
O40.0120 (6)0.0300 (7)0.0360 (7)0.0001 (5)0.0007 (5)0.0086 (6)
C10.0201 (8)0.0162 (8)0.0194 (8)0.0032 (7)−0.0043 (7)−0.0043 (6)
C20.0202 (8)0.0180 (8)0.0164 (7)0.0022 (7)−0.0036 (6)−0.0038 (6)
C30.0133 (7)0.0177 (8)0.0137 (7)−0.0002 (6)−0.0020 (6)−0.0023 (6)
C40.0213 (8)0.0201 (8)0.0127 (7)0.0002 (7)−0.0005 (6)0.0000 (6)
C50.0181 (8)0.0191 (8)0.0139 (7)−0.0029 (7)0.0037 (6)0.0006 (6)
C60.0113 (7)0.0148 (7)0.0130 (7)−0.0007 (6)0.0005 (6)0.0012 (6)
C70.0107 (7)0.0136 (7)0.0154 (7)−0.0012 (6)0.0003 (6)−0.0008 (6)
C80.0142 (8)0.0156 (7)0.0173 (7)−0.0021 (6)0.0028 (6)0.0011 (6)
C90.0118 (7)0.0138 (7)0.0226 (8)−0.0017 (6)0.0005 (6)0.0011 (6)
C100.0112 (7)0.0135 (7)0.0212 (8)0.0001 (6)0.0002 (6)−0.0008 (6)
C110.0173 (8)0.0151 (8)0.0258 (8)0.0002 (7)0.0015 (7)−0.0032 (7)
C120.0201 (8)0.0196 (8)0.0280 (9)−0.0004 (7)−0.0019 (7)−0.0087 (7)
C130.0247 (9)0.0220 (8)0.0241 (8)0.0043 (8)−0.0052 (7)−0.0084 (7)
C140.0171 (8)0.0189 (8)0.0180 (8)0.0051 (7)−0.0038 (7)−0.0051 (6)
C150.0124 (7)0.0141 (7)0.0179 (7)0.0018 (6)−0.0006 (6)−0.0011 (6)
C160.0115 (7)0.0145 (7)0.0131 (7)0.0027 (6)−0.0016 (6)−0.0003 (6)
C170.0162 (8)0.0173 (8)0.0139 (7)0.0011 (7)0.0016 (6)−0.0008 (6)
C180.0190 (8)0.0166 (7)0.0163 (7)−0.0049 (7)0.0051 (7)−0.0004 (6)
C190.0127 (7)0.0143 (7)0.0136 (7)−0.0012 (6)0.0006 (6)0.0000 (6)
C200.0138 (7)0.0152 (7)0.0140 (7)−0.0011 (6)−0.0009 (6)−0.0010 (6)
C210.0239 (8)0.0152 (7)0.0176 (8)−0.0023 (7)0.0016 (7)−0.0008 (6)
C220.0257 (9)0.0139 (7)0.0223 (8)−0.0009 (7)0.0003 (7)−0.0007 (6)
C230.0335 (11)0.0246 (9)0.0259 (9)0.0117 (9)0.0013 (8)0.0008 (7)
C240.0532 (14)0.0212 (9)0.0398 (11)0.0116 (10)0.0032 (11)−0.0044 (9)
C250.0317 (10)0.0211 (9)0.0241 (9)0.0026 (8)−0.0143 (8)−0.0051 (7)
C260.0303 (10)0.0269 (10)0.0208 (8)0.0014 (8)0.0049 (7)−0.0077 (7)
C270.0135 (7)0.0177 (8)0.0185 (7)0.0003 (6)−0.0024 (6)0.0012 (6)
C280.0109 (7)0.0184 (8)0.0209 (8)0.0008 (6)−0.0002 (6)−0.0031 (6)
C290.0141 (8)0.0137 (7)0.0241 (8)0.0007 (6)−0.0006 (6)−0.0005 (6)
C300.0181 (8)0.0290 (9)0.0395 (10)0.0015 (8)−0.0091 (8)0.0122 (8)
C310.0456 (13)0.0302 (10)0.0481 (13)0.0059 (10)−0.0271 (11)−0.0149 (10)
C320.0353 (10)0.0229 (9)0.0206 (8)0.0057 (8)−0.0093 (8)−0.0014 (7)
C330.0138 (8)0.0193 (8)0.0276 (8)−0.0004 (7)−0.0022 (7)−0.0045 (7)
Geometric parameters (Å, °) top
O1—C231.343 (2)C14—H141.0000
O1—C11.459 (2)C15—C161.525 (2)
O2—C231.191 (3)C15—H151.0000
O3—C291.351 (2)C16—C171.326 (2)
O3—C301.446 (2)C17—C181.500 (2)
O4—C291.205 (2)C17—H170.9500
C1—C221.515 (2)C18—C191.535 (2)
C1—C21.539 (2)C18—H18A0.9900
C1—H11.0000C18—H18B0.9900
C2—C251.532 (2)C19—C201.572 (2)
C2—C261.535 (3)C19—H191.0000
C2—C31.562 (2)C20—C211.541 (2)
C3—C41.533 (2)C20—C331.554 (2)
C3—C201.552 (2)C21—C221.530 (2)
C3—H31.0000C21—H21A0.9900
C4—C51.530 (2)C21—H21B0.9900
C4—H4A0.9900C22—H22A0.9900
C4—H4B0.9900C22—H22B0.9900
C5—C61.544 (2)C23—C241.497 (3)
C5—H5A0.9900C24—H24A0.9800
C5—H5B0.9900C24—H24B0.9800
C6—C271.548 (2)C24—H24C0.9800
C6—C191.555 (2)C25—H25A0.9800
C6—C71.591 (2)C25—H25B0.9800
C7—C161.535 (2)C25—H25C0.9800
C7—C81.551 (2)C26—H26A0.9800
C7—C281.554 (2)C26—H26B0.9800
C8—C91.529 (2)C26—H26C0.9800
C8—H8A0.9900C27—H27A0.9800
C8—H8B0.9900C27—H27B0.9800
C9—C101.533 (2)C27—H27C0.9800
C9—H9A0.9900C28—H28A0.9800
C9—H9B0.9900C28—H28B0.9800
C10—C291.528 (2)C28—H28C0.9800
C10—C151.542 (2)C30—H30A0.9800
C10—C111.547 (2)C30—H30B0.9800
C11—C121.525 (2)C30—H30C0.9800
C11—H11A0.9900C31—H31A0.9800
C11—H11B0.9900C31—H31B0.9800
C12—C131.526 (3)C31—H31C0.9800
C12—H12A0.9900C32—H32A0.9800
C12—H12B0.9900C32—H32B0.9800
C13—C311.530 (3)C32—H32C0.9800
C13—C141.540 (2)C33—H33A0.9800
C13—H131.0000C33—H33B0.9800
C14—C321.530 (2)C33—H33C0.9800
C14—C151.561 (2)
C23—O1—C1118.81 (15)C15—C16—C7119.72 (14)
C29—O3—C30115.02 (14)C16—C17—C18125.83 (15)
O1—C1—C22106.87 (14)C16—C17—H17117.1
O1—C1—C2108.62 (13)C18—C17—H17117.1
C22—C1—C2115.04 (14)C17—C18—C19113.80 (13)
O1—C1—H1108.7C17—C18—H18A108.8
C22—C1—H1108.7C19—C18—H18A108.8
C2—C1—H1108.7C17—C18—H18B108.8
C25—C2—C26107.72 (14)C19—C18—H18B108.8
C25—C2—C1111.91 (15)H18A—C18—H18B107.7
C26—C2—C1107.31 (15)C18—C19—C6110.02 (12)
C25—C2—C3113.71 (14)C18—C19—C20113.22 (13)
C26—C2—C3108.88 (14)C6—C19—C20117.85 (12)
C1—C2—C3107.11 (12)C18—C19—H19104.8
C4—C3—C20109.75 (13)C6—C19—H19104.8
C4—C3—C2114.15 (12)C20—C19—H19104.8
C20—C3—C2117.36 (14)C21—C20—C3108.33 (13)
C4—C3—H3104.7C21—C20—C33107.15 (14)
C20—C3—H3104.7C3—C20—C33113.73 (13)
C2—C3—H3104.7C21—C20—C19107.63 (12)
C5—C4—C3110.66 (13)C3—C20—C19105.84 (13)
C5—C4—H4A109.5C33—C20—C19113.90 (13)
C3—C4—H4A109.5C22—C21—C20113.38 (13)
C5—C4—H4B109.5C22—C21—H21A108.9
C3—C4—H4B109.5C20—C21—H21A108.9
H4A—C4—H4B108.1C22—C21—H21B108.9
C4—C5—C6114.17 (14)C20—C21—H21B108.9
C4—C5—H5A108.7H21A—C21—H21B107.7
C6—C5—H5A108.7C1—C22—C21110.20 (14)
C4—C5—H5B108.7C1—C22—H22A109.6
C6—C5—H5B108.7C21—C22—H22A109.6
H5A—C5—H5B107.6C1—C22—H22B109.6
C5—C6—C27107.91 (12)C21—C22—H22B109.6
C5—C6—C19110.64 (12)H22A—C22—H22B108.1
C27—C6—C19110.76 (13)O2—C23—O1124.20 (19)
C5—C6—C7110.36 (12)O2—C23—C24124.88 (19)
C27—C6—C7109.84 (12)O1—C23—C24110.92 (18)
C19—C6—C7107.34 (12)C23—C24—H24A109.5
C16—C7—C8112.01 (13)C23—C24—H24B109.5
C16—C7—C28107.05 (12)H24A—C24—H24B109.5
C8—C7—C28107.09 (13)C23—C24—H24C109.5
C16—C7—C6108.88 (12)H24A—C24—H24C109.5
C8—C7—C6109.53 (12)H24B—C24—H24C109.5
C28—C7—C6112.29 (12)C2—C25—H25A109.5
C9—C8—C7114.71 (13)C2—C25—H25B109.5
C9—C8—H8A108.6H25A—C25—H25B109.5
C7—C8—H8A108.6C2—C25—H25C109.5
C9—C8—H8B108.6H25A—C25—H25C109.5
C7—C8—H8B108.6H25B—C25—H25C109.5
H8A—C8—H8B107.6C2—C26—H26A109.5
C8—C9—C10111.69 (13)C2—C26—H26B109.5
C8—C9—H9A109.3H26A—C26—H26B109.5
C10—C9—H9A109.3C2—C26—H26C109.5
C8—C9—H9B109.3H26A—C26—H26C109.5
C10—C9—H9B109.3H26B—C26—H26C109.5
H9A—C9—H9B107.9C6—C27—H27A109.5
C29—C10—C9111.76 (13)C6—C27—H27B109.5
C29—C10—C15108.50 (13)H27A—C27—H27B109.5
C9—C10—C15109.50 (13)C6—C27—H27C109.5
C29—C10—C11104.39 (13)H27A—C27—H27C109.5
C9—C10—C11111.83 (13)H27B—C27—H27C109.5
C15—C10—C11110.73 (13)C7—C28—H28A109.5
C12—C11—C10112.04 (14)C7—C28—H28B109.5
C12—C11—H11A109.2H28A—C28—H28B109.5
C10—C11—H11A109.2C7—C28—H28C109.5
C12—C11—H11B109.2H28A—C28—H28C109.5
C10—C11—H11B109.2H28B—C28—H28C109.5
H11A—C11—H11B107.9O4—C29—O3122.26 (16)
C11—C12—C13111.89 (15)O4—C29—C10125.60 (15)
C11—C12—H12A109.2O3—C29—C10112.09 (14)
C13—C12—H12A109.2O3—C30—H30A109.5
C11—C12—H12B109.2O3—C30—H30B109.5
C13—C12—H12B109.2H30A—C30—H30B109.5
H12A—C12—H12B107.9O3—C30—H30C109.5
C12—C13—C31109.33 (17)H30A—C30—H30C109.5
C12—C13—C14111.85 (14)H30B—C30—H30C109.5
C31—C13—C14111.87 (15)C13—C31—H31A109.5
C12—C13—H13107.9C13—C31—H31B109.5
C31—C13—H13107.9H31A—C31—H31B109.5
C14—C13—H13107.9C13—C31—H31C109.5
C32—C14—C13110.53 (14)H31A—C31—H31C109.5
C32—C14—C15110.22 (14)H31B—C31—H31C109.5
C13—C14—C15110.96 (13)C14—C32—H32A109.5
C32—C14—H14108.4C14—C32—H32B109.5
C13—C14—H14108.3H32A—C32—H32B109.5
C15—C14—H14108.3C14—C32—H32C109.5
C16—C15—C10110.48 (12)H32A—C32—H32C109.5
C16—C15—C14112.93 (13)H32B—C32—H32C109.5
C10—C15—C14113.12 (13)C20—C33—H33A109.5
C16—C15—H15106.6C20—C33—H33B109.5
C10—C15—H15106.6H33A—C33—H33B109.5
C14—C15—H15106.6C20—C33—H33C109.5
C17—C16—C15119.36 (14)H33A—C33—H33C109.5
C17—C16—C7120.84 (14)H33B—C33—H33C109.5
C23—O1—C1—C22115.74 (17)C13—C14—C15—C16−178.48 (14)
C23—O1—C1—C2−119.58 (17)C32—C14—C15—C10−174.81 (13)
O1—C1—C2—C25−46.91 (19)C13—C14—C15—C10−52.05 (18)
C22—C1—C2—C2572.79 (18)C10—C15—C16—C17137.94 (15)
O1—C1—C2—C2671.06 (17)C14—C15—C16—C17−94.23 (18)
C22—C1—C2—C26−169.24 (14)C10—C15—C16—C7−45.42 (19)
O1—C1—C2—C3−172.16 (14)C14—C15—C16—C782.41 (17)
C22—C1—C2—C3−52.46 (19)C8—C7—C16—C17−147.40 (15)
C25—C2—C3—C456.7 (2)C28—C7—C16—C1795.51 (18)
C26—C2—C3—C4−63.39 (18)C6—C7—C16—C17−26.1 (2)
C1—C2—C3—C4−179.13 (15)C8—C7—C16—C1536.01 (19)
C25—C2—C3—C20−73.76 (18)C28—C7—C16—C15−81.08 (16)
C26—C2—C3—C20166.14 (14)C6—C7—C16—C15157.30 (13)
C1—C2—C3—C2050.40 (18)C15—C16—C17—C18174.87 (15)
C20—C3—C4—C5−65.11 (17)C7—C16—C17—C18−1.7 (3)
C2—C3—C4—C5160.77 (15)C16—C17—C18—C19−3.2 (2)
C3—C4—C5—C655.33 (19)C17—C18—C19—C636.47 (18)
C4—C5—C6—C2777.97 (17)C17—C18—C19—C20170.68 (13)
C4—C5—C6—C19−43.35 (18)C5—C6—C19—C18175.97 (13)
C4—C5—C6—C7−162.01 (13)C27—C6—C19—C1856.35 (16)
C5—C6—C7—C16178.09 (13)C7—C6—C19—C18−63.56 (16)
C27—C6—C7—C16−63.05 (15)C5—C6—C19—C2044.13 (19)
C19—C6—C7—C1657.44 (15)C27—C6—C19—C20−75.49 (17)
C5—C6—C7—C8−59.12 (16)C7—C6—C19—C20164.60 (13)
C27—C6—C7—C859.74 (16)C4—C3—C20—C21176.26 (13)
C19—C6—C7—C8−179.77 (12)C2—C3—C20—C21−51.26 (18)
C5—C6—C7—C2859.72 (16)C4—C3—C20—C33−64.72 (17)
C27—C6—C7—C28178.58 (12)C2—C3—C20—C3367.75 (18)
C19—C6—C7—C28−60.93 (15)C4—C3—C20—C1961.07 (15)
C16—C7—C8—C9−38.61 (19)C2—C3—C20—C19−166.46 (13)
C28—C7—C8—C978.46 (16)C18—C19—C20—C2161.10 (17)
C6—C7—C8—C9−159.53 (13)C6—C19—C20—C21−168.51 (13)
C7—C8—C9—C1053.32 (19)C18—C19—C20—C3176.77 (13)
C8—C9—C10—C2958.72 (17)C6—C19—C20—C3−52.84 (17)
C8—C9—C10—C15−61.54 (17)C18—C19—C20—C33−57.54 (18)
C8—C9—C10—C11175.34 (13)C6—C19—C20—C3372.85 (17)
C29—C10—C11—C12−170.26 (14)C3—C20—C21—C2252.64 (18)
C9—C10—C11—C1268.73 (18)C33—C20—C21—C22−70.44 (17)
C15—C10—C11—C12−53.68 (18)C19—C20—C21—C22166.66 (15)
C10—C11—C12—C1356.19 (19)O1—C1—C22—C21178.07 (13)
C11—C12—C13—C31179.52 (15)C2—C1—C22—C2157.41 (19)
C11—C12—C13—C14−56.0 (2)C20—C21—C22—C1−56.75 (19)
C12—C13—C14—C32175.81 (16)C1—O1—C23—O23.3 (3)
C31—C13—C14—C32−61.2 (2)C1—O1—C23—C24−177.37 (15)
C12—C13—C14—C1553.2 (2)C30—O3—C29—O4−0.1 (3)
C31—C13—C14—C15176.25 (16)C30—O3—C29—C10177.34 (15)
C29—C10—C15—C16−66.28 (16)C9—C10—C29—O4−145.43 (17)
C9—C10—C15—C1655.95 (17)C15—C10—C29—O4−24.6 (2)
C11—C10—C15—C16179.71 (13)C11—C10—C29—O493.5 (2)
C29—C10—C15—C14166.00 (13)C9—C10—C29—O337.18 (19)
C9—C10—C15—C14−71.78 (16)C15—C10—C29—O3158.02 (13)
C11—C10—C15—C1451.99 (17)C11—C10—C29—O3−83.87 (16)
C32—C14—C15—C1658.75 (17)
Acknowledgements top

We thank the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 nd SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Ma, C.-M., Cai, S.-Q., Chui, J. R., Wang, R.-Q., Tu, P.-F., Hattori, M. & Daneshtalab, M. (2005). Eur. J. Med. Chem. 40, 582–589.

Paton, W. F. & Paul, I. C. (1979). Cryst. Struct. Commun. 8, 207–211.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Simon, A., Delage, C., Saux, M., Chulia, A. J., Najid, A. & Rigaud, M. (1992). Acta Cryst. C48, 726–728.

Stout, G. H. & Stevens, K. L. (1963). J. Org. Chem. 28, 1259–1262.

Westrip, S. P. (2009). publCIF. In preparation.