PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2802–o2803.
Published online 2010 October 13. doi:  10.1107/S1600536810039942
PMCID: PMC3009069

R,4R,4aR,6aS,7R,8S,10R,11S)-Methyl α-acet­oxy-4-(3-furan­yl)-10-hy­droxy-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzopyran-8-acetate (6-O-acetyl­swietenolide) from the seeds of Swietenia macrophylla

Abstract

The mol­ecule of O-acetyl­swietenolide, C29H36O9, isolated from the seeds of Swietenia macrophylla, features four six-membered rings connected together in the shape of a bowl; one of the inner rings adopts a twisted chair conformation owing to the C=C double bond. The furyl substitutent is connected to an outer ring, and it points away from the bowl cavity. The hy­droxy group is connected to a carbonyl O atom of an adjacent mol­ecule by an O—H(...)O hydrogen bond, generating a chain running along the b axis.

Related literature

For the absolute stereochemistry assignment, see: Bickii et al. (2000 [triangle]); Kadota et al. (1990 [triangle]); Mootoo et al. (1999 [triangle]); Narender et al. (2008 [triangle]). For another swietenolide isolated from Swietenia macrophylla, see: Goh et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2802-scheme1.jpg

Experimental

Crystal data

  • C29H36O9
  • M r = 528.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2802-efi1.jpg
  • a = 11.5648 (9) Å
  • b = 8.4355 (6) Å
  • c = 14.5082 (11) Å
  • β = 112.985 (1)°
  • V = 1302.98 (17) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.35 × 0.15 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 12419 measured reflections
  • 3178 independent reflections
  • 2952 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.100
  • S = 1.00
  • 3178 reflections
  • 353 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039942/bt5372sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039942/bt5372Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Sweietenia macrophylla is a large mahogany tree growing in the rainforests of Malaysia. The extracts of the seeds contain flavonoids, saponins and alkaloids that are commecialized in local herbal products. A previous study reports the crystal structure of swietenolide diactate (Goh et al., 2010). The title compound (Scheme I, Fig. 1), which was isolated from the same plant, differs only in having a hydroxy group in place of a acetoxy group. The hydroxy group engages in O–H···O hydrogen bonding to generate a chain structure.

Experimental

The finely ground seeds ofSweietenia macrophylla (600 g) were soaked in ethanol at room temperature for three days. The mixture was filtered and the solvent evaporated to give a dark yellow crude material (70 g). A portion (40 g) was successively extracted with n-hexane, ethyl acetate and water to give an n-hexane-insoluble residue. The residue was partitioned between ethyl acetate-water (1:1) to give an ethyl acetate-soluble fraction (30 g, 80%).

This fraction (3 g) was subjected to column chromatography on silica gel (70–230 mesh, 300 g), with initial elution by n-hexane, followed by increasing proportions of chloroform. Eleven fractions were obtained. The fourth fraction (2 g) was further subjected to column chromatography (70–230 mesh,200 g), initially eluting with n-hexane and later with acetone to give twelve fractions.

The eighth fraction (600 mg) was dissolved in methanol and kept in a refrigerator. A white solid was obtained after two days, and a second crop was obtained after another two days. Recrystallization of the first crop from chloroform yielded colorless crystals of the swietenolide diacetate (yield 15 mg). The ninth fraction (80 mg) yielded O-acetylswietenolide (13 mg) after recrystalization from chloroform.

Refinement

Carbon-bound H atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The hydroxy H-atom was located in a difference Fourier map, and was refined isotropically with a distance restraint of O–H 0.84±0.01 Å.

2201 Friedel pairs were merged.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C29H36O9 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C29H36O9F(000) = 564
Mr = 528.58Dx = 1.347 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4876 reflections
a = 11.5648 (9) Åθ = 2.9–28.1°
b = 8.4355 (6) ŵ = 0.10 mm1
c = 14.5082 (11) ÅT = 100 K
β = 112.985 (1)°Prism, colorless
V = 1302.98 (17) Å30.35 × 0.15 × 0.05 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer2952 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
graphiteθmax = 27.5°, θmin = 1.9°
ω scansh = −15→15
12419 measured reflectionsk = −10→10
3178 independent reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0733P)2 + 0.1429P] where P = (Fo2 + 2Fc2)/3
3178 reflections(Δ/σ)max = 0.001
353 parametersΔρmax = 0.27 e Å3
2 restraintsΔρmin = −0.20 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.61851 (17)0.5009 (2)1.01707 (12)0.0283 (4)
O20.47929 (19)1.1423 (2)0.73073 (15)0.0344 (4)
O30.55291 (15)0.92107 (19)0.81247 (12)0.0198 (3)
O40.87219 (16)0.6373 (2)0.44745 (12)0.0257 (4)
O50.89022 (14)0.99908 (19)0.69927 (12)0.0200 (3)
H50.945 (2)1.059 (3)0.7393 (18)0.024 (7)*
O60.92901 (15)0.6390 (2)0.91487 (12)0.0264 (4)
O71.12489 (15)0.5429 (2)0.96568 (11)0.0224 (4)
O81.06597 (15)0.21550 (19)0.82808 (12)0.0218 (3)
O91.10687 (14)0.46053 (18)0.78928 (12)0.0169 (3)
C10.4977 (2)0.5532 (3)0.98089 (18)0.0268 (5)
H10.43650.52021.00540.032*
C20.4760 (2)0.6575 (3)0.90604 (17)0.0237 (5)
H20.39900.70970.86880.028*
C30.5928 (2)0.6741 (3)0.89368 (16)0.0184 (4)
C40.6748 (2)0.5781 (3)0.96307 (17)0.0252 (5)
H40.76050.56600.97300.030*
C50.61902 (19)0.7714 (3)0.81867 (16)0.0162 (4)
H5A0.71120.79370.84510.019*
C60.5376 (2)1.0223 (3)0.73623 (17)0.0200 (4)
C70.5993 (2)0.9818 (3)0.66575 (16)0.0174 (4)
H7A0.68141.03700.68920.021*
H7B0.54711.02610.59930.021*
C80.62213 (18)0.8084 (3)0.65186 (15)0.0144 (4)
C90.57977 (19)0.6948 (3)0.71383 (16)0.0156 (4)
C100.4363 (2)0.6743 (3)0.66379 (17)0.0203 (5)
H10A0.41330.63340.59570.030*
H10B0.39550.77700.66100.030*
H10C0.40880.59950.70280.030*
C110.6478 (2)0.5347 (2)0.72606 (16)0.0159 (4)
H11A0.73480.54600.77620.019*
H11B0.60460.45530.75170.019*
C120.6513 (2)0.4750 (3)0.62825 (16)0.0178 (4)
H12A0.56460.45030.58130.021*
H12B0.70020.37510.64150.021*
C130.70907 (19)0.5924 (3)0.57788 (16)0.0159 (4)
H130.66770.57060.50440.019*
C140.67811 (19)0.7634 (3)0.59133 (15)0.0148 (4)
C150.7178 (2)0.8800 (3)0.53024 (16)0.0183 (4)
H15A0.70450.98910.54930.022*
H15B0.66380.86550.45850.022*
C160.8571 (2)0.8611 (3)0.54462 (17)0.0186 (4)
H160.87120.92380.49140.022*
C170.8692 (2)0.6869 (3)0.52527 (16)0.0189 (4)
C180.85658 (19)0.5781 (3)0.60545 (16)0.0153 (4)
C190.8895 (2)0.4080 (3)0.58576 (17)0.0189 (4)
H19A0.83200.37420.51890.028*
H19B0.88130.33640.63610.028*
H19C0.97600.40500.58970.028*
C200.93657 (19)0.6467 (2)0.71258 (15)0.0125 (4)
H200.87500.70490.73290.015*
C211.03242 (19)0.7743 (3)0.71073 (16)0.0154 (4)
C220.9545 (2)0.9152 (3)0.64803 (17)0.0185 (4)
H221.01390.99060.63610.022*
C231.1253 (2)0.7223 (3)0.66323 (18)0.0211 (5)
H23A1.18430.64420.70670.032*
H23B1.17190.81490.65550.032*
H23C1.07850.67480.59750.032*
C241.1129 (2)0.8349 (3)0.81604 (17)0.0198 (5)
H24A1.17010.75080.85410.030*
H24B1.05820.86560.85030.030*
H24C1.16180.92700.81100.030*
C250.99178 (19)0.5175 (2)0.79253 (15)0.0146 (4)
H250.93100.42710.77530.018*
C261.0111 (2)0.5757 (3)0.89756 (16)0.0179 (4)
C271.1475 (3)0.5980 (4)1.06570 (19)0.0352 (7)
H27A1.23820.60541.10470.053*
H27B1.11050.52331.09820.053*
H27C1.10920.70271.06200.053*
C281.1339 (2)0.3050 (3)0.80775 (16)0.0166 (4)
C291.2531 (2)0.2641 (3)0.79648 (18)0.0216 (5)
H29A1.23560.24380.72580.032*
H29B1.28980.16910.83590.032*
H29C1.31230.35260.82040.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0289 (9)0.0383 (10)0.0209 (8)−0.0019 (8)0.0133 (7)0.0061 (7)
O20.0402 (11)0.0271 (9)0.0458 (11)0.0131 (9)0.0274 (9)0.0032 (9)
O30.0224 (8)0.0193 (7)0.0225 (8)−0.0008 (6)0.0140 (7)−0.0051 (6)
O40.0284 (9)0.0365 (9)0.0172 (8)0.0106 (8)0.0142 (7)0.0037 (7)
O50.0157 (7)0.0171 (7)0.0276 (9)0.0008 (6)0.0090 (7)0.0000 (6)
O60.0182 (8)0.0465 (10)0.0158 (8)0.0061 (8)0.0079 (6)−0.0018 (8)
O70.0201 (8)0.0307 (9)0.0139 (7)0.0063 (7)0.0038 (6)0.0016 (7)
O80.0229 (8)0.0159 (7)0.0267 (9)0.0003 (6)0.0097 (7)0.0020 (7)
O90.0141 (7)0.0146 (7)0.0230 (8)0.0029 (6)0.0084 (6)0.0025 (6)
C10.0251 (11)0.0347 (13)0.0254 (12)−0.0046 (10)0.0150 (10)−0.0012 (10)
C20.0208 (11)0.0304 (12)0.0249 (12)−0.0033 (10)0.0142 (9)−0.0012 (10)
C30.0196 (10)0.0231 (11)0.0150 (10)−0.0037 (9)0.0096 (8)−0.0058 (8)
C40.0219 (11)0.0363 (13)0.0198 (11)−0.0019 (10)0.0105 (9)0.0025 (10)
C50.0134 (9)0.0197 (10)0.0170 (10)−0.0018 (8)0.0077 (8)−0.0030 (8)
C60.0172 (10)0.0220 (10)0.0223 (11)0.0000 (9)0.0095 (9)−0.0044 (9)
C70.0158 (10)0.0195 (10)0.0182 (10)0.0031 (8)0.0081 (8)0.0009 (8)
C80.0081 (9)0.0189 (10)0.0132 (10)0.0018 (7)0.0010 (7)−0.0003 (8)
C90.0116 (9)0.0203 (10)0.0151 (9)−0.0016 (8)0.0053 (8)−0.0032 (8)
C100.0137 (10)0.0282 (12)0.0199 (10)−0.0035 (9)0.0076 (8)−0.0071 (9)
C110.0161 (9)0.0175 (10)0.0167 (10)−0.0035 (8)0.0094 (8)−0.0018 (8)
C120.0165 (10)0.0189 (10)0.0200 (10)−0.0024 (8)0.0091 (8)−0.0044 (8)
C130.0116 (9)0.0201 (10)0.0152 (10)0.0017 (8)0.0045 (8)−0.0032 (8)
C140.0105 (9)0.0203 (10)0.0124 (9)0.0026 (8)0.0031 (7)0.0008 (8)
C150.0147 (10)0.0249 (10)0.0156 (10)0.0057 (9)0.0063 (8)0.0051 (9)
C160.0183 (11)0.0241 (11)0.0182 (10)0.0055 (8)0.0123 (9)0.0081 (9)
C170.0136 (10)0.0274 (11)0.0172 (10)0.0050 (8)0.0077 (8)0.0045 (9)
C180.0131 (9)0.0193 (10)0.0146 (9)0.0019 (8)0.0066 (8)0.0007 (8)
C190.0188 (10)0.0228 (11)0.0174 (10)0.0027 (9)0.0096 (9)−0.0033 (8)
C200.0108 (8)0.0141 (9)0.0127 (9)0.0029 (7)0.0045 (7)0.0010 (7)
C210.0129 (9)0.0161 (9)0.0201 (10)0.0013 (8)0.0096 (8)0.0029 (8)
C220.0154 (10)0.0159 (10)0.0260 (11)0.0030 (8)0.0102 (9)0.0068 (8)
C230.0134 (10)0.0234 (10)0.0303 (12)0.0039 (8)0.0126 (9)0.0074 (9)
C240.0148 (10)0.0168 (10)0.0259 (12)−0.0007 (8)0.0058 (9)0.0002 (8)
C250.0127 (9)0.0145 (9)0.0173 (10)0.0012 (8)0.0065 (8)0.0014 (8)
C260.0169 (10)0.0218 (10)0.0157 (10)−0.0007 (9)0.0071 (8)0.0028 (8)
C270.0271 (13)0.0530 (18)0.0161 (11)0.0144 (13)−0.0017 (10)−0.0026 (11)
C280.0178 (10)0.0147 (10)0.0139 (10)0.0019 (8)0.0026 (8)−0.0014 (8)
C290.0183 (10)0.0187 (10)0.0276 (12)0.0055 (9)0.0089 (9)−0.0002 (9)

Geometric parameters (Å, °)

O1—C11.360 (3)C12—H12B0.9900
O1—C41.364 (3)C13—C141.518 (3)
O2—C61.202 (3)C13—C181.597 (3)
O3—C61.353 (3)C13—H131.0000
O3—C51.461 (3)C14—C151.510 (3)
O4—C171.217 (3)C15—C161.550 (3)
O5—C221.427 (3)C15—H15A0.9900
O5—H50.84 (1)C15—H15B0.9900
O6—C261.198 (3)C16—C171.513 (3)
O7—C261.330 (3)C16—C221.552 (3)
O7—C271.447 (3)C16—H161.0000
O8—C281.206 (3)C17—C181.533 (3)
O9—C281.351 (3)C18—C191.540 (3)
O9—C251.433 (2)C18—C201.576 (3)
C1—C21.343 (4)C19—H19A0.9800
C1—H10.9500C19—H19B0.9800
C2—C31.438 (3)C19—H19C0.9800
C2—H20.9500C20—C251.537 (3)
C3—C41.350 (3)C20—C211.553 (3)
C3—C51.486 (3)C20—H201.0000
C4—H40.9500C21—C241.533 (3)
C5—C91.548 (3)C21—C231.549 (3)
C5—H5A1.0000C21—C221.553 (3)
C6—C71.497 (3)C22—H221.0000
C7—C81.513 (3)C23—H23A0.9800
C7—H7A0.9900C23—H23B0.9800
C7—H7B0.9900C23—H23C0.9800
C8—C141.333 (3)C24—H24A0.9800
C8—C91.520 (3)C24—H24B0.9800
C9—C111.538 (3)C24—H24C0.9800
C9—C101.539 (3)C25—C261.532 (3)
C10—H10A0.9800C25—H251.0000
C10—H10B0.9800C27—H27A0.9800
C10—H10C0.9800C27—H27B0.9800
C11—C121.521 (3)C27—H27C0.9800
C11—H11A0.9900C28—C291.490 (3)
C11—H11B0.9900C29—H29A0.9800
C12—C131.530 (3)C29—H29B0.9800
C12—H12A0.9900C29—H29C0.9800
C1—O1—C4105.78 (19)C17—C16—C22112.35 (18)
C6—O3—C5119.61 (16)C15—C16—C22115.07 (18)
C22—O5—H5104 (2)C17—C16—H16108.4
C26—O7—C27114.67 (18)C15—C16—H16108.4
C28—O9—C25117.71 (17)C22—C16—H16108.4
C2—C1—O1111.4 (2)O4—C17—C16123.0 (2)
C2—C1—H1124.3O4—C17—C18122.9 (2)
O1—C1—H1124.3C16—C17—C18113.45 (18)
C1—C2—C3106.0 (2)C17—C18—C19108.29 (17)
C1—C2—H2127.0C17—C18—C20109.63 (18)
C3—C2—H2127.0C19—C18—C20115.63 (17)
C4—C3—C2105.6 (2)C17—C18—C13100.00 (16)
C4—C3—C5126.4 (2)C19—C18—C13109.91 (18)
C2—C3—C5128.0 (2)C20—C18—C13112.19 (16)
C3—C4—O1111.2 (2)C18—C19—H19A109.5
C3—C4—H4124.4C18—C19—H19B109.5
O1—C4—H4124.4H19A—C19—H19B109.5
O3—C5—C3105.74 (16)C18—C19—H19C109.5
O3—C5—C9110.76 (17)H19A—C19—H19C109.5
C3—C5—C9115.06 (18)H19B—C19—H19C109.5
O3—C5—H5A108.4C25—C20—C21114.55 (16)
C3—C5—H5A108.4C25—C20—C18113.28 (17)
C9—C5—H5A108.4C21—C20—C18112.67 (16)
O2—C6—O3118.5 (2)C25—C20—H20105.1
O2—C6—C7123.5 (2)C21—C20—H20105.1
O3—C6—C7117.99 (19)C18—C20—H20105.1
C6—C7—C8117.74 (19)C24—C21—C23106.33 (18)
C6—C7—H7A107.9C24—C21—C20111.93 (17)
C8—C7—H7A107.9C23—C21—C20115.78 (18)
C6—C7—H7B107.9C24—C21—C22108.43 (18)
C8—C7—H7B107.9C23—C21—C22107.51 (17)
H7A—C7—H7B107.2C20—C21—C22106.60 (16)
C14—C8—C7121.15 (19)O5—C22—C16108.69 (17)
C14—C8—C9124.17 (19)O5—C22—C21112.06 (17)
C7—C8—C9114.66 (17)C16—C22—C21112.18 (18)
C8—C9—C11110.70 (16)O5—C22—H22107.9
C8—C9—C10109.21 (18)C16—C22—H22107.9
C11—C9—C10111.35 (18)C21—C22—H22107.9
C8—C9—C5106.23 (16)C21—C23—H23A109.5
C11—C9—C5108.21 (17)C21—C23—H23B109.5
C10—C9—C5111.03 (17)H23A—C23—H23B109.5
C9—C10—H10A109.5C21—C23—H23C109.5
C9—C10—H10B109.5H23A—C23—H23C109.5
H10A—C10—H10B109.5H23B—C23—H23C109.5
C9—C10—H10C109.5C21—C24—H24A109.5
H10A—C10—H10C109.5C21—C24—H24B109.5
H10B—C10—H10C109.5H24A—C24—H24B109.5
C12—C11—C9112.46 (17)C21—C24—H24C109.5
C12—C11—H11A109.1H24A—C24—H24C109.5
C9—C11—H11A109.1H24B—C24—H24C109.5
C12—C11—H11B109.1O9—C25—C26111.32 (17)
C9—C11—H11B109.1O9—C25—C20109.29 (16)
H11A—C11—H11B107.8C26—C25—C20112.31 (17)
C11—C12—C13114.02 (17)O9—C25—H25107.9
C11—C12—H12A108.7C26—C25—H25107.9
C13—C12—H12A108.7C20—C25—H25107.9
C11—C12—H12B108.7O6—C26—O7124.9 (2)
C13—C12—H12B108.7O6—C26—C25122.11 (19)
H12A—C12—H12B107.6O7—C26—C25112.95 (18)
C14—C13—C12112.65 (17)O7—C27—H27A109.5
C14—C13—C18108.77 (17)O7—C27—H27B109.5
C12—C13—C18117.01 (18)H27A—C27—H27B109.5
C14—C13—H13105.9O7—C27—H27C109.5
C12—C13—H13105.9H27A—C27—H27C109.5
C18—C13—H13105.9H27B—C27—H27C109.5
C8—C14—C15122.6 (2)O8—C28—O9122.2 (2)
C8—C14—C13123.70 (19)O8—C28—C29126.9 (2)
C15—C14—C13113.74 (17)O9—C28—C29110.79 (19)
C14—C15—C16113.10 (17)C28—C29—H29A109.5
C14—C15—H15A109.0C28—C29—H29B109.5
C16—C15—H15A109.0H29A—C29—H29B109.5
C14—C15—H15B109.0C28—C29—H29C109.5
C16—C15—H15B109.0H29A—C29—H29C109.5
H15A—C15—H15B107.8H29B—C29—H29C109.5
C17—C16—C15103.94 (19)
C4—O1—C1—C20.9 (3)C15—C16—C17—C18−68.0 (2)
O1—C1—C2—C3−0.4 (3)C22—C16—C17—C1857.1 (2)
C1—C2—C3—C4−0.3 (3)O4—C17—C18—C1917.1 (3)
C1—C2—C3—C5177.9 (2)C16—C17—C18—C19−171.89 (18)
C2—C3—C4—O10.9 (3)O4—C17—C18—C20144.1 (2)
C5—C3—C4—O1−177.3 (2)C16—C17—C18—C20−44.9 (2)
C1—O1—C4—C3−1.1 (3)O4—C17—C18—C13−97.9 (2)
C6—O3—C5—C3−166.70 (18)C16—C17—C18—C1373.1 (2)
C6—O3—C5—C9−41.4 (2)C14—C13—C18—C17−62.5 (2)
C4—C3—C5—O3−140.9 (2)C12—C13—C18—C17168.46 (18)
C2—C3—C5—O341.3 (3)C14—C13—C18—C19−176.26 (17)
C4—C3—C5—C996.5 (3)C12—C13—C18—C1954.7 (2)
C2—C3—C5—C9−81.3 (3)C14—C13—C18—C2053.6 (2)
C5—O3—C6—O2177.6 (2)C12—C13—C18—C20−75.4 (2)
C5—O3—C6—C7−5.1 (3)C17—C18—C20—C25−147.54 (17)
O2—C6—C7—C8−155.4 (2)C19—C18—C20—C25−24.8 (2)
O3—C6—C7—C827.5 (3)C13—C18—C20—C25102.3 (2)
C6—C7—C8—C14−179.1 (2)C17—C18—C20—C21−15.5 (2)
C6—C7—C8—C9−0.7 (3)C19—C18—C20—C21107.2 (2)
C14—C8—C9—C1119.3 (3)C13—C18—C20—C21−125.63 (18)
C7—C8—C9—C11−159.00 (18)C25—C20—C21—C24−46.3 (2)
C14—C8—C9—C10−103.6 (2)C18—C20—C21—C24−177.77 (17)
C7—C8—C9—C1078.1 (2)C25—C20—C21—C2375.7 (2)
C14—C8—C9—C5136.6 (2)C18—C20—C21—C23−55.7 (2)
C7—C8—C9—C5−41.7 (2)C25—C20—C21—C22−164.74 (17)
O3—C5—C9—C863.6 (2)C18—C20—C21—C2263.8 (2)
C3—C5—C9—C8−176.52 (18)C17—C16—C22—O5−129.80 (18)
O3—C5—C9—C11−177.45 (16)C15—C16—C22—O5−11.1 (2)
C3—C5—C9—C11−57.6 (2)C17—C16—C22—C21−5.3 (2)
O3—C5—C9—C10−55.0 (2)C15—C16—C22—C21113.3 (2)
C3—C5—C9—C1064.9 (2)C24—C21—C22—O5−49.9 (2)
C8—C9—C11—C12−45.1 (2)C23—C21—C22—O5−164.50 (18)
C10—C9—C11—C1276.6 (2)C20—C21—C22—O570.7 (2)
C5—C9—C11—C12−161.11 (17)C24—C21—C22—C16−172.51 (17)
C9—C11—C12—C1355.3 (2)C23—C21—C22—C1672.9 (2)
C11—C12—C13—C14−35.6 (3)C20—C21—C22—C16−51.8 (2)
C11—C12—C13—C1891.5 (2)C28—O9—C25—C2690.9 (2)
C7—C8—C14—C15−2.3 (3)C28—O9—C25—C20−144.50 (18)
C9—C8—C14—C15179.45 (19)C21—C20—C25—O9−47.2 (2)
C7—C8—C14—C13177.06 (19)C18—C20—C25—O984.0 (2)
C9—C8—C14—C13−1.2 (3)C21—C20—C25—C2676.9 (2)
C12—C13—C14—C88.9 (3)C18—C20—C25—C26−151.96 (17)
C18—C13—C14—C8−122.5 (2)C27—O7—C26—O6−3.3 (4)
C12—C13—C14—C15−171.68 (18)C27—O7—C26—C25179.2 (2)
C18—C13—C14—C1556.9 (2)O9—C25—C26—O6174.3 (2)
C8—C14—C15—C16127.9 (2)C20—C25—C26—O651.4 (3)
C13—C14—C15—C16−51.6 (3)O9—C25—C26—O7−8.1 (3)
C14—C15—C16—C1752.2 (2)C20—C25—C26—O7−131.01 (19)
C14—C15—C16—C22−71.1 (2)C25—O9—C28—O8−1.2 (3)
C15—C16—C17—O4103.1 (2)C25—O9—C28—C29177.21 (17)
C22—C16—C17—O4−131.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5···O8i0.84 (1)1.99 (1)2.827 (2)175 (3)

Symmetry codes: (i) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5372).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bickii, J., Njifutie, N., Ayafo Foyere, J., Basco, L. K. & Ringwald, P. (2000). J. Enthnopharmacol.69, 27–33. [PubMed]
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Goh, B. H., Abdul Kadir, H., Abdul Malek, S. N. & Ng, S. W. (2010). Acta Cryst. E66, o1396. [PMC free article] [PubMed]
  • Kadota, S., Maraung, L., Kikuchi, T. & Ekimoto, H. (1990). Chem. Pharm. Bull.36, 639–651.
  • Mootoo, B. S., Ali, A., Motilal, R., Pingal, R., Ramlal, A., Khan, A., Reynolds, W. F. & McLean, S. (1999). J. Nat. Prod.62, 1515–1517. [PubMed]
  • Narender, T., Khaliq, T. & Shweta, T. (2008). Nat. Prod. Res. A22, 763–800. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography