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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Aug 8;65(Pt 9):o2114. doi: 10.1107/S1600536809030657

Methyl 3-acet­oxy-3-dehydroxy­ursolate

Nor Hayati Abdullah a, Khalijah Awang b, Noel F Thomas b, Seik Weng Ng b,*
PMCID: PMC2969982  PMID: 21577529

Abstract

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

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 ▶).graphic file with name e-65-o2114-scheme1.jpg

Experimental

Crystal data

  • C33H52O4

  • M r = 512.75

  • Orthorhombic, Inline graphic

  • a = 6.8245 (1) Å

  • b = 13.4874 (2) Å

  • c = 32.2233 (5) Å

  • V = 2965.99 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.30 × 0.15 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 28565 measured reflections

  • 3886 independent reflections

  • 3612 reflections with I > 2σ(I)

  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036

  • wR(F 2) = 0.099

  • S = 1.07

  • 3886 reflections

  • 343 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030657/xu2574sup1.cif

e-65-o2114-sup1.cif (28.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030657/xu2574Isup2.hkl

e-65-o2114-Isup2.hkl (190.5KB, hkl)

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

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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.

Crystal data

C33H52O4 F(000) = 1128
Mr = 512.75 Dx = 1.148 Mg m−3
Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 9010 reflections
a = 6.8245 (1) Å θ = 2.4–28.2°
b = 13.4874 (2) Å µ = 0.07 mm−1
c = 32.2233 (5) Å T = 100 K
V = 2965.99 (8) Å3 Block, colorless
Z = 4 0.30 × 0.15 × 0.05 mm
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Data collection

Bruker SMART APEX diffractometer 3612 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.034
graphite θmax = 27.5°, θmin = 1.6°
ω scans h = −8→8
28565 measured reflections k = −17→17
3886 independent reflections l = −41→41
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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)] = 0.036 H-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 reflections Δρmax = 0.35 e Å−3
343 parameters Δρmin = −0.18 e Å−3
0 restraints Absolute structure: Friedel pairs were merged.
Primary atom site location: structure-invariant direct methods
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.8683 (2) 0.63811 (9) 0.94880 (4) 0.0230 (3)
O2 0.5731 (2) 0.69609 (13) 0.93041 (6) 0.0470 (4)
O3 1.03757 (18) −0.18360 (9) 0.86981 (4) 0.0233 (3)
O4 1.20002 (18) −0.09494 (10) 0.82218 (4) 0.0260 (3)
C1 0.8406 (3) 0.54575 (12) 0.92596 (5) 0.0186 (3)
H1 0.7088 0.5471 0.9124 0.022*
C2 0.8468 (3) 0.45891 (13) 0.95692 (5) 0.0182 (3)
C3 0.8466 (2) 0.36120 (12) 0.93090 (5) 0.0149 (3)
H3 0.7162 0.3605 0.9167 0.018*
C4 0.8493 (3) 0.26628 (12) 0.95708 (5) 0.0180 (3)
H4A 0.9840 0.2539 0.9672 0.022*
H4B 0.7628 0.2747 0.9815 0.022*
C5 0.7799 (3) 0.17749 (12) 0.93146 (5) 0.0170 (3)
H5A 0.6399 0.1869 0.9245 0.020*
H5B 0.7903 0.1169 0.9487 0.020*
C6 0.8959 (2) 0.16124 (12) 0.89087 (5) 0.0130 (3)
C7 0.7757 (2) 0.09206 (12) 0.86003 (5) 0.0132 (3)
C8 0.7354 (2) −0.00924 (12) 0.88113 (5) 0.0157 (3)
H8A 0.8521 −0.0281 0.8976 0.019*
H8B 0.6246 −0.0013 0.9007 0.019*
C9 0.6875 (2) −0.09377 (12) 0.85118 (5) 0.0161 (3)
H9A 0.5591 −0.0809 0.8379 0.019*
H9B 0.6772 −0.1566 0.8669 0.019*
C10 0.8445 (2) −0.10472 (12) 0.81746 (5) 0.0153 (3)
C11 0.8054 (3) −0.19544 (12) 0.78927 (6) 0.0194 (3)
H11A 0.9208 −0.2068 0.7713 0.023*
H11B 0.7873 −0.2550 0.8068 0.023*
C12 0.6244 (3) −0.18105 (13) 0.76217 (6) 0.0226 (4)
H12A 0.5069 −0.1769 0.7801 0.027*
H12B 0.6088 −0.2393 0.7438 0.027*
C13 0.6387 (3) −0.08737 (13) 0.73579 (6) 0.0236 (4)
H13 0.7532 −0.0950 0.7167 0.028*
C14 0.6737 (3) 0.00559 (12) 0.76254 (5) 0.0180 (3)
H14 0.5554 0.0166 0.7803 0.022*
C15 0.8546 (2) −0.00871 (12) 0.79156 (5) 0.0148 (3)
H15 0.9717 −0.0151 0.7731 0.018*
C16 0.8921 (2) 0.08048 (12) 0.81955 (5) 0.0130 (3)
C17 1.0181 (2) 0.14961 (12) 0.80750 (5) 0.0158 (3)
H17 1.0886 0.1375 0.7826 0.019*
C18 1.0591 (3) 0.24517 (12) 0.82969 (5) 0.0173 (3)
H18A 1.0380 0.3009 0.8102 0.021*
H18B 1.1986 0.2462 0.8381 0.021*
C19 0.9313 (2) 0.26154 (11) 0.86828 (5) 0.0135 (3)
H19 0.8000 0.2808 0.8571 0.016*
C20 0.9982 (2) 0.35270 (12) 0.89520 (5) 0.0144 (3)
C21 0.9818 (3) 0.44612 (12) 0.86787 (5) 0.0189 (3)
H21A 1.0873 0.4448 0.8468 0.023*
H21B 0.8549 0.4447 0.8530 0.023*
C22 0.9963 (3) 0.54291 (12) 0.89246 (5) 0.0206 (4)
H22A 1.1277 0.5482 0.9053 0.025*
H22B 0.9788 0.6000 0.8735 0.025*
C23 0.7261 (3) 0.70689 (15) 0.94762 (6) 0.0280 (4)
C24 0.7851 (4) 0.79780 (15) 0.97118 (7) 0.0381 (5)
H24A 0.6719 0.8420 0.9740 0.057*
H24B 0.8899 0.8322 0.9562 0.057*
H24C 0.8322 0.7787 0.9988 0.057*
C25 1.0202 (3) 0.46737 (14) 0.98688 (6) 0.0256 (4)
H25A 0.9960 0.5213 1.0066 0.038*
H25B 1.1401 0.4813 0.9712 0.038*
H25C 1.0357 0.4049 1.0020 0.038*
C26 0.6580 (3) 0.46347 (15) 0.98272 (6) 0.0260 (4)
H26A 0.6476 0.5286 0.9960 0.039*
H26B 0.6611 0.4117 1.0041 0.039*
H26C 0.5447 0.4530 0.9646 0.039*
C27 1.0929 (2) 0.11123 (12) 0.90219 (5) 0.0166 (3)
H27A 1.1746 0.1581 0.9177 0.025*
H27B 1.1610 0.0914 0.8767 0.025*
H27C 1.0679 0.0525 0.9193 0.025*
C28 0.5736 (2) 0.13716 (12) 0.84835 (5) 0.0167 (3)
H28A 0.4877 0.0848 0.8377 0.025*
H28B 0.5916 0.1879 0.8269 0.025*
H28C 0.5142 0.1672 0.8730 0.025*
C29 1.0468 (3) −0.12439 (12) 0.83603 (5) 0.0173 (3)
C30 1.2249 (3) −0.20894 (15) 0.88788 (7) 0.0288 (4)
H30A 1.2043 −0.2512 0.9122 0.043*
H30B 1.2930 −0.1482 0.8963 0.043*
H30C 1.3043 −0.2445 0.8674 0.043*
C31 0.4540 (4) −0.07768 (16) 0.70914 (8) 0.0413 (6)
H31A 0.4315 −0.1398 0.6941 0.062*
H31B 0.4711 −0.0235 0.6892 0.062*
H31C 0.3412 −0.0636 0.7270 0.062*
C32 0.7024 (3) 0.09685 (14) 0.73502 (5) 0.0263 (4)
H32A 0.5835 0.1083 0.7187 0.039*
H32B 0.8135 0.0858 0.7163 0.039*
H32C 0.7285 0.1549 0.7525 0.039*
C33 1.2140 (3) 0.34623 (13) 0.91040 (6) 0.0202 (4)
H33A 1.2638 0.4131 0.9158 0.030*
H33B 1.2945 0.3145 0.8890 0.030*
H33C 1.2198 0.3070 0.9360 0.030*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0271 (7) 0.0157 (6) 0.0262 (6) 0.0066 (5) −0.0052 (5) −0.0058 (5)
O2 0.0382 (9) 0.0427 (9) 0.0601 (10) 0.0214 (8) −0.0182 (8) −0.0115 (8)
O3 0.0138 (6) 0.0226 (6) 0.0335 (7) −0.0004 (5) −0.0040 (5) 0.0111 (5)
O4 0.0120 (6) 0.0300 (7) 0.0360 (7) 0.0001 (5) 0.0007 (5) 0.0086 (6)
C1 0.0201 (8) 0.0162 (8) 0.0194 (8) 0.0032 (7) −0.0043 (7) −0.0043 (6)
C2 0.0202 (8) 0.0180 (8) 0.0164 (7) 0.0022 (7) −0.0036 (6) −0.0038 (6)
C3 0.0133 (7) 0.0177 (8) 0.0137 (7) −0.0002 (6) −0.0020 (6) −0.0023 (6)
C4 0.0213 (8) 0.0201 (8) 0.0127 (7) 0.0002 (7) −0.0005 (6) 0.0000 (6)
C5 0.0181 (8) 0.0191 (8) 0.0139 (7) −0.0029 (7) 0.0037 (6) 0.0006 (6)
C6 0.0113 (7) 0.0148 (7) 0.0130 (7) −0.0007 (6) 0.0005 (6) 0.0012 (6)
C7 0.0107 (7) 0.0136 (7) 0.0154 (7) −0.0012 (6) 0.0003 (6) −0.0008 (6)
C8 0.0142 (8) 0.0156 (7) 0.0173 (7) −0.0021 (6) 0.0028 (6) 0.0011 (6)
C9 0.0118 (7) 0.0138 (7) 0.0226 (8) −0.0017 (6) 0.0005 (6) 0.0011 (6)
C10 0.0112 (7) 0.0135 (7) 0.0212 (8) 0.0001 (6) 0.0002 (6) −0.0008 (6)
C11 0.0173 (8) 0.0151 (8) 0.0258 (8) 0.0002 (7) 0.0015 (7) −0.0032 (7)
C12 0.0201 (8) 0.0196 (8) 0.0280 (9) −0.0004 (7) −0.0019 (7) −0.0087 (7)
C13 0.0247 (9) 0.0220 (8) 0.0241 (8) 0.0043 (8) −0.0052 (7) −0.0084 (7)
C14 0.0171 (8) 0.0189 (8) 0.0180 (8) 0.0051 (7) −0.0038 (7) −0.0051 (6)
C15 0.0124 (7) 0.0141 (7) 0.0179 (7) 0.0018 (6) −0.0006 (6) −0.0011 (6)
C16 0.0115 (7) 0.0145 (7) 0.0131 (7) 0.0027 (6) −0.0016 (6) −0.0003 (6)
C17 0.0162 (8) 0.0173 (8) 0.0139 (7) 0.0011 (7) 0.0016 (6) −0.0008 (6)
C18 0.0190 (8) 0.0166 (7) 0.0163 (7) −0.0049 (7) 0.0051 (7) −0.0004 (6)
C19 0.0127 (7) 0.0143 (7) 0.0136 (7) −0.0012 (6) 0.0006 (6) 0.0000 (6)
C20 0.0138 (7) 0.0152 (7) 0.0140 (7) −0.0011 (6) −0.0009 (6) −0.0010 (6)
C21 0.0239 (8) 0.0152 (7) 0.0176 (8) −0.0023 (7) 0.0016 (7) −0.0008 (6)
C22 0.0257 (9) 0.0139 (7) 0.0223 (8) −0.0009 (7) 0.0003 (7) −0.0007 (6)
C23 0.0335 (11) 0.0246 (9) 0.0259 (9) 0.0117 (9) 0.0013 (8) 0.0008 (7)
C24 0.0532 (14) 0.0212 (9) 0.0398 (11) 0.0116 (10) 0.0032 (11) −0.0044 (9)
C25 0.0317 (10) 0.0211 (9) 0.0241 (9) 0.0026 (8) −0.0143 (8) −0.0051 (7)
C26 0.0303 (10) 0.0269 (10) 0.0208 (8) 0.0014 (8) 0.0049 (7) −0.0077 (7)
C27 0.0135 (7) 0.0177 (8) 0.0185 (7) 0.0003 (6) −0.0024 (6) 0.0012 (6)
C28 0.0109 (7) 0.0184 (8) 0.0209 (8) 0.0008 (6) −0.0002 (6) −0.0031 (6)
C29 0.0141 (8) 0.0137 (7) 0.0241 (8) 0.0007 (6) −0.0006 (6) −0.0005 (6)
C30 0.0181 (8) 0.0290 (9) 0.0395 (10) 0.0015 (8) −0.0091 (8) 0.0122 (8)
C31 0.0456 (13) 0.0302 (10) 0.0481 (13) 0.0059 (10) −0.0271 (11) −0.0149 (10)
C32 0.0353 (10) 0.0229 (9) 0.0206 (8) 0.0057 (8) −0.0093 (8) −0.0014 (7)
C33 0.0138 (8) 0.0193 (8) 0.0276 (8) −0.0004 (7) −0.0022 (7) −0.0045 (7)
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Geometric parameters (Å, °)

O1—C23 1.343 (2) C14—H14 1.0000
O1—C1 1.459 (2) C15—C16 1.525 (2)
O2—C23 1.191 (3) C15—H15 1.0000
O3—C29 1.351 (2) C16—C17 1.326 (2)
O3—C30 1.446 (2) C17—C18 1.500 (2)
O4—C29 1.205 (2) C17—H17 0.9500
C1—C22 1.515 (2) C18—C19 1.535 (2)
C1—C2 1.539 (2) C18—H18A 0.9900
C1—H1 1.0000 C18—H18B 0.9900
C2—C25 1.532 (2) C19—C20 1.572 (2)
C2—C26 1.535 (3) C19—H19 1.0000
C2—C3 1.562 (2) C20—C21 1.541 (2)
C3—C4 1.533 (2) C20—C33 1.554 (2)
C3—C20 1.552 (2) C21—C22 1.530 (2)
C3—H3 1.0000 C21—H21A 0.9900
C4—C5 1.530 (2) C21—H21B 0.9900
C4—H4A 0.9900 C22—H22A 0.9900
C4—H4B 0.9900 C22—H22B 0.9900
C5—C6 1.544 (2) C23—C24 1.497 (3)
C5—H5A 0.9900 C24—H24A 0.9800
C5—H5B 0.9900 C24—H24B 0.9800
C6—C27 1.548 (2) C24—H24C 0.9800
C6—C19 1.555 (2) C25—H25A 0.9800
C6—C7 1.591 (2) C25—H25B 0.9800
C7—C16 1.535 (2) C25—H25C 0.9800
C7—C8 1.551 (2) C26—H26A 0.9800
C7—C28 1.554 (2) C26—H26B 0.9800
C8—C9 1.529 (2) C26—H26C 0.9800
C8—H8A 0.9900 C27—H27A 0.9800
C8—H8B 0.9900 C27—H27B 0.9800
C9—C10 1.533 (2) C27—H27C 0.9800
C9—H9A 0.9900 C28—H28A 0.9800
C9—H9B 0.9900 C28—H28B 0.9800
C10—C29 1.528 (2) C28—H28C 0.9800
C10—C15 1.542 (2) C30—H30A 0.9800
C10—C11 1.547 (2) C30—H30B 0.9800
C11—C12 1.525 (2) C30—H30C 0.9800
C11—H11A 0.9900 C31—H31A 0.9800
C11—H11B 0.9900 C31—H31B 0.9800
C12—C13 1.526 (3) C31—H31C 0.9800
C12—H12A 0.9900 C32—H32A 0.9800
C12—H12B 0.9900 C32—H32B 0.9800
C13—C31 1.530 (3) C32—H32C 0.9800
C13—C14 1.540 (2) C33—H33A 0.9800
C13—H13 1.0000 C33—H33B 0.9800
C14—C32 1.530 (2) C33—H33C 0.9800
C14—C15 1.561 (2)
C23—O1—C1 118.81 (15) C15—C16—C7 119.72 (14)
C29—O3—C30 115.02 (14) C16—C17—C18 125.83 (15)
O1—C1—C22 106.87 (14) C16—C17—H17 117.1
O1—C1—C2 108.62 (13) C18—C17—H17 117.1
C22—C1—C2 115.04 (14) C17—C18—C19 113.80 (13)
O1—C1—H1 108.7 C17—C18—H18A 108.8
C22—C1—H1 108.7 C19—C18—H18A 108.8
C2—C1—H1 108.7 C17—C18—H18B 108.8
C25—C2—C26 107.72 (14) C19—C18—H18B 108.8
C25—C2—C1 111.91 (15) H18A—C18—H18B 107.7
C26—C2—C1 107.31 (15) C18—C19—C6 110.02 (12)
C25—C2—C3 113.71 (14) C18—C19—C20 113.22 (13)
C26—C2—C3 108.88 (14) C6—C19—C20 117.85 (12)
C1—C2—C3 107.11 (12) C18—C19—H19 104.8
C4—C3—C20 109.75 (13) C6—C19—H19 104.8
C4—C3—C2 114.15 (12) C20—C19—H19 104.8
C20—C3—C2 117.36 (14) C21—C20—C3 108.33 (13)
C4—C3—H3 104.7 C21—C20—C33 107.15 (14)
C20—C3—H3 104.7 C3—C20—C33 113.73 (13)
C2—C3—H3 104.7 C21—C20—C19 107.63 (12)
C5—C4—C3 110.66 (13) C3—C20—C19 105.84 (13)
C5—C4—H4A 109.5 C33—C20—C19 113.90 (13)
C3—C4—H4A 109.5 C22—C21—C20 113.38 (13)
C5—C4—H4B 109.5 C22—C21—H21A 108.9
C3—C4—H4B 109.5 C20—C21—H21A 108.9
H4A—C4—H4B 108.1 C22—C21—H21B 108.9
C4—C5—C6 114.17 (14) C20—C21—H21B 108.9
C4—C5—H5A 108.7 H21A—C21—H21B 107.7
C6—C5—H5A 108.7 C1—C22—C21 110.20 (14)
C4—C5—H5B 108.7 C1—C22—H22A 109.6
C6—C5—H5B 108.7 C21—C22—H22A 109.6
H5A—C5—H5B 107.6 C1—C22—H22B 109.6
C5—C6—C27 107.91 (12) C21—C22—H22B 109.6
C5—C6—C19 110.64 (12) H22A—C22—H22B 108.1
C27—C6—C19 110.76 (13) O2—C23—O1 124.20 (19)
C5—C6—C7 110.36 (12) O2—C23—C24 124.88 (19)
C27—C6—C7 109.84 (12) O1—C23—C24 110.92 (18)
C19—C6—C7 107.34 (12) C23—C24—H24A 109.5
C16—C7—C8 112.01 (13) C23—C24—H24B 109.5
C16—C7—C28 107.05 (12) H24A—C24—H24B 109.5
C8—C7—C28 107.09 (13) C23—C24—H24C 109.5
C16—C7—C6 108.88 (12) H24A—C24—H24C 109.5
C8—C7—C6 109.53 (12) H24B—C24—H24C 109.5
C28—C7—C6 112.29 (12) C2—C25—H25A 109.5
C9—C8—C7 114.71 (13) C2—C25—H25B 109.5
C9—C8—H8A 108.6 H25A—C25—H25B 109.5
C7—C8—H8A 108.6 C2—C25—H25C 109.5
C9—C8—H8B 108.6 H25A—C25—H25C 109.5
C7—C8—H8B 108.6 H25B—C25—H25C 109.5
H8A—C8—H8B 107.6 C2—C26—H26A 109.5
C8—C9—C10 111.69 (13) C2—C26—H26B 109.5
C8—C9—H9A 109.3 H26A—C26—H26B 109.5
C10—C9—H9A 109.3 C2—C26—H26C 109.5
C8—C9—H9B 109.3 H26A—C26—H26C 109.5
C10—C9—H9B 109.3 H26B—C26—H26C 109.5
H9A—C9—H9B 107.9 C6—C27—H27A 109.5
C29—C10—C9 111.76 (13) C6—C27—H27B 109.5
C29—C10—C15 108.50 (13) H27A—C27—H27B 109.5
C9—C10—C15 109.50 (13) C6—C27—H27C 109.5
C29—C10—C11 104.39 (13) H27A—C27—H27C 109.5
C9—C10—C11 111.83 (13) H27B—C27—H27C 109.5
C15—C10—C11 110.73 (13) C7—C28—H28A 109.5
C12—C11—C10 112.04 (14) C7—C28—H28B 109.5
C12—C11—H11A 109.2 H28A—C28—H28B 109.5
C10—C11—H11A 109.2 C7—C28—H28C 109.5
C12—C11—H11B 109.2 H28A—C28—H28C 109.5
C10—C11—H11B 109.2 H28B—C28—H28C 109.5
H11A—C11—H11B 107.9 O4—C29—O3 122.26 (16)
C11—C12—C13 111.89 (15) O4—C29—C10 125.60 (15)
C11—C12—H12A 109.2 O3—C29—C10 112.09 (14)
C13—C12—H12A 109.2 O3—C30—H30A 109.5
C11—C12—H12B 109.2 O3—C30—H30B 109.5
C13—C12—H12B 109.2 H30A—C30—H30B 109.5
H12A—C12—H12B 107.9 O3—C30—H30C 109.5
C12—C13—C31 109.33 (17) H30A—C30—H30C 109.5
C12—C13—C14 111.85 (14) H30B—C30—H30C 109.5
C31—C13—C14 111.87 (15) C13—C31—H31A 109.5
C12—C13—H13 107.9 C13—C31—H31B 109.5
C31—C13—H13 107.9 H31A—C31—H31B 109.5
C14—C13—H13 107.9 C13—C31—H31C 109.5
C32—C14—C13 110.53 (14) H31A—C31—H31C 109.5
C32—C14—C15 110.22 (14) H31B—C31—H31C 109.5
C13—C14—C15 110.96 (13) C14—C32—H32A 109.5
C32—C14—H14 108.4 C14—C32—H32B 109.5
C13—C14—H14 108.3 H32A—C32—H32B 109.5
C15—C14—H14 108.3 C14—C32—H32C 109.5
C16—C15—C10 110.48 (12) H32A—C32—H32C 109.5
C16—C15—C14 112.93 (13) H32B—C32—H32C 109.5
C10—C15—C14 113.12 (13) C20—C33—H33A 109.5
C16—C15—H15 106.6 C20—C33—H33B 109.5
C10—C15—H15 106.6 H33A—C33—H33B 109.5
C14—C15—H15 106.6 C20—C33—H33C 109.5
C17—C16—C15 119.36 (14) H33A—C33—H33C 109.5
C17—C16—C7 120.84 (14) H33B—C33—H33C 109.5
C23—O1—C1—C22 115.74 (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—C25 72.79 (18) C10—C15—C16—C17 137.94 (15)
O1—C1—C2—C26 71.06 (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—C7 82.41 (17)
C22—C1—C2—C3 −52.46 (19) C8—C7—C16—C17 −147.40 (15)
C25—C2—C3—C4 56.7 (2) C28—C7—C16—C17 95.51 (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—C15 36.01 (19)
C25—C2—C3—C20 −73.76 (18) C28—C7—C16—C15 −81.08 (16)
C26—C2—C3—C20 166.14 (14) C6—C7—C16—C15 157.30 (13)
C1—C2—C3—C20 50.40 (18) C15—C16—C17—C18 174.87 (15)
C20—C3—C4—C5 −65.11 (17) C7—C16—C17—C18 −1.7 (3)
C2—C3—C4—C5 160.77 (15) C16—C17—C18—C19 −3.2 (2)
C3—C4—C5—C6 55.33 (19) C17—C18—C19—C6 36.47 (18)
C4—C5—C6—C27 77.97 (17) C17—C18—C19—C20 170.68 (13)
C4—C5—C6—C19 −43.35 (18) C5—C6—C19—C18 175.97 (13)
C4—C5—C6—C7 −162.01 (13) C27—C6—C19—C18 56.35 (16)
C5—C6—C7—C16 178.09 (13) C7—C6—C19—C18 −63.56 (16)
C27—C6—C7—C16 −63.05 (15) C5—C6—C19—C20 44.13 (19)
C19—C6—C7—C16 57.44 (15) C27—C6—C19—C20 −75.49 (17)
C5—C6—C7—C8 −59.12 (16) C7—C6—C19—C20 164.60 (13)
C27—C6—C7—C8 59.74 (16) C4—C3—C20—C21 176.26 (13)
C19—C6—C7—C8 −179.77 (12) C2—C3—C20—C21 −51.26 (18)
C5—C6—C7—C28 59.72 (16) C4—C3—C20—C33 −64.72 (17)
C27—C6—C7—C28 178.58 (12) C2—C3—C20—C33 67.75 (18)
C19—C6—C7—C28 −60.93 (15) C4—C3—C20—C19 61.07 (15)
C16—C7—C8—C9 −38.61 (19) C2—C3—C20—C19 −166.46 (13)
C28—C7—C8—C9 78.46 (16) C18—C19—C20—C21 61.10 (17)
C6—C7—C8—C9 −159.53 (13) C6—C19—C20—C21 −168.51 (13)
C7—C8—C9—C10 53.32 (19) C18—C19—C20—C3 176.77 (13)
C8—C9—C10—C29 58.72 (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—C11 175.34 (13) C6—C19—C20—C33 72.85 (17)
C29—C10—C11—C12 −170.26 (14) C3—C20—C21—C22 52.64 (18)
C9—C10—C11—C12 68.73 (18) C33—C20—C21—C22 −70.44 (17)
C15—C10—C11—C12 −53.68 (18) C19—C20—C21—C22 166.66 (15)
C10—C11—C12—C13 56.19 (19) O1—C1—C22—C21 178.07 (13)
C11—C12—C13—C31 179.52 (15) C2—C1—C22—C21 57.41 (19)
C11—C12—C13—C14 −56.0 (2) C20—C21—C22—C1 −56.75 (19)
C12—C13—C14—C32 175.81 (16) C1—O1—C23—O2 3.3 (3)
C31—C13—C14—C32 −61.2 (2) C1—O1—C23—C24 −177.37 (15)
C12—C13—C14—C15 53.2 (2) C30—O3—C29—O4 −0.1 (3)
C31—C13—C14—C15 176.25 (16) C30—O3—C29—C10 177.34 (15)
C29—C10—C15—C16 −66.28 (16) C9—C10—C29—O4 −145.43 (17)
C9—C10—C15—C16 55.95 (17) C15—C10—C29—O4 −24.6 (2)
C11—C10—C15—C16 179.71 (13) C11—C10—C29—O4 93.5 (2)
C29—C10—C15—C14 166.00 (13) C9—C10—C29—O3 37.18 (19)
C9—C10—C15—C14 −71.78 (16) C15—C10—C29—O3 158.02 (13)
C11—C10—C15—C14 51.99 (17) C11—C10—C29—O3 −83.87 (16)
C32—C14—C15—C16 58.75 (17)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2574).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  2. Bruker (2008). APEX2 nd SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. 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. [DOI] [PubMed]
  4. Paton, W. F. & Paul, I. C. (1979). Cryst. Struct. Commun.8, 207–211.
  5. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  6. Simon, A., Delage, C., Saux, M., Chulia, A. J., Najid, A. & Rigaud, M. (1992). Acta Cryst. C48, 726–728.
  7. Stout, G. H. & Stevens, K. L. (1963). J. Org. Chem.28, 1259–1262.
  8. Westrip, S. P. (2009). publCIF In preparation.

Associated Data

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

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030657/xu2574sup1.cif

e-65-o2114-sup1.cif (28.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030657/xu2574Isup2.hkl

e-65-o2114-Isup2.hkl (190.5KB, 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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