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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1317.
Published online 2009 May 20. doi:  10.1107/S1600536809015955
PMCID: PMC2969541

Pinnatane A from the bark of Walsura pinnata Hassk

Abstract

In the mol­ecule of pinnatane A, C30H48O3, isolated from the bark of Walsura pinnata Hassk, the four cyclo­hexane rings adopt chair conformations; the carboxyl and hydr­oxy substituents occupy axial positions. The cyclo­hexene ring is envelope-shaped. Adjacent mol­ecules are linked by O—H(...)O hydrogen bonds into a chain running along the c axis.

Related literature

For related structures, see: Awang et al. (2009 [triangle]); Jiang et al. (1995 [triangle]).

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Object name is e-65-o1317-scheme1.jpg

Experimental

Crystal data

  • C30H48O3
  • M r = 456.68
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1317-efi1.jpg
  • a = 7.3761 (2) Å
  • b = 16.3585 (4) Å
  • c = 20.7032 (5) Å
  • V = 2498.1 (1) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.40 × 0.15 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 17614 measured reflections
  • 3268 independent reflections
  • 2881 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.097
  • S = 1.00
  • 3268 reflections
  • 313 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015955/wn2325sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015955/wn2325Isup2.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

Chemicals from Walsura pinnata Hassk have not hitherto been reported. We have recently reported the structure of 3-oxoolean-1-en-28-oic acid (Awang et al., 2009), which was obtained from one fraction of the crude extract of the bark of this plant. The last fraction yielded the title compound, which we have named pinnatane A. A related carbon skeleton, assigned from spectroscopic measurements, has been reported (Jiang et al., 1995).

In the molecule of pinnatane A (Fig. 1) the four cyclohexane rings adopt chair comformations, with axial carboxylic acid and hydroxy substituents. The cyclohexene ring is envelope-shaped. Adjacent molecules are linked by O—H···O hydrogen bonds into a chain running along the longest axis of the orthorhombic unit cell.

Experimental

The dried and ground bark of Walsura pinnata Hassk (2.3 kg) was extracted with n-hexane for 72 h at room temperature. The solvent was evaporated to give a crude extract, which was subjected to column chromatography on silica gel (60 GF254), using n-hexane with increasing amounts of ethyl acetate as eluent. Of the twenty-four fractions collected, the twenty-fourth fraction, eluted with ethyl acetate:n-hexane (14:86) gave 2 g of the product, which was further purified by column chromatography (n-hexane:acetone, 94:6) to give the title compound (5 mg). The formulation was established by satisfactory solution NMR spectroscopy.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). The oxygen-bound H-atoms were located in a difference Fourier map, and were refined with a distance restraint of 0.84±0.01 Å; their displacement parameters were freely refined. In the absence of significant anomalous scattering effects, Friedel pairs were merged.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C30H48O3F(000) = 1008
Mr = 456.68Dx = 1.214 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3887 reflections
a = 7.3761 (2) Åθ = 2.3–28.0°
b = 16.3585 (4) ŵ = 0.08 mm1
c = 20.7032 (5) ÅT = 100 K
V = 2498.1 (1) Å3Chip, colorless
Z = 40.40 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer2881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
graphiteθmax = 27.5°, θmin = 1.6°
ω scansh = −9→9
17614 measured reflectionsk = −21→21
3268 independent reflectionsl = −26→25

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0608P)2 + 0.3281P] where P = (Fo2 + 2Fc2)/3
3268 reflections(Δ/σ)max = 0.001
313 parametersΔρmax = 0.27 e Å3
2 restraintsΔρmin = −0.17 e Å3

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

xyzUiso*/Ueq
O10.0192 (2)1.08616 (9)−0.04603 (8)0.0226 (3)
H10.022 (5)1.1379 (6)−0.0479 (15)0.054 (9)*
O20.2787 (2)1.10407 (8)0.00673 (6)0.0191 (3)
O30.5137 (2)0.74943 (9)0.43439 (7)0.0219 (3)
H30.590 (3)0.7286 (16)0.4595 (11)0.040 (8)*
C10.1662 (3)1.05839 (11)−0.01560 (9)0.0145 (4)
C20.1730 (3)0.96355 (11)−0.01453 (9)0.0131 (4)
C30.1421 (3)0.93705 (12)−0.08573 (9)0.0168 (4)
H3A0.14470.8766−0.08840.020*
H3B0.02080.9556−0.09990.020*
C40.2849 (3)0.97201 (13)−0.13099 (10)0.0209 (4)
H4A0.26951.0321−0.13330.025*
H4B0.26500.9497−0.17490.025*
C50.4827 (3)0.95261 (13)−0.10968 (9)0.0197 (4)
C60.4780 (3)0.90007 (12)−0.04821 (9)0.0181 (4)
H6A0.60420.8920−0.03320.022*
H6B0.42900.8456−0.05960.022*
C70.3656 (3)0.93451 (11)0.00866 (9)0.0129 (4)
H70.43060.98440.02420.015*
C80.5911 (3)1.03113 (14)−0.09846 (11)0.0267 (5)
H8A0.52941.0649−0.06610.040*
H8B0.60051.0616−0.13910.040*
H8C0.71291.0172−0.08300.040*
C90.5782 (4)0.90337 (16)−0.16263 (10)0.0323 (6)
H9A0.51270.8521−0.16990.049*
H9B0.70280.8913−0.14920.049*
H9C0.58020.9352−0.20270.049*
C100.3632 (3)0.87291 (11)0.06662 (9)0.0118 (4)
C110.3079 (3)0.78698 (11)0.04270 (9)0.0159 (4)
H11A0.41040.76160.02030.024*
H11B0.20510.79180.01290.024*
H11C0.27290.75310.07970.024*
C120.2315 (3)0.90314 (11)0.12067 (8)0.0116 (4)
C130.0361 (3)0.89617 (12)0.09446 (9)0.0148 (4)
H13A−0.04640.92500.12450.018*
H13B0.00090.83780.09430.018*
C140.0073 (3)0.93116 (12)0.02569 (9)0.0172 (4)
H14A−0.08050.97670.02940.021*
H14B−0.05200.8880−0.00030.021*
C150.2605 (3)0.99440 (11)0.13609 (9)0.0151 (4)
H15A0.21381.00630.17940.023*
H15B0.19581.02780.10430.023*
H15C0.39021.00710.13440.023*
C160.2508 (3)0.84795 (11)0.18263 (9)0.0116 (4)
H160.21220.79200.16880.014*
C170.4463 (3)0.83731 (11)0.20946 (9)0.0126 (4)
C180.5718 (3)0.81296 (12)0.15331 (9)0.0147 (4)
H18A0.69880.81350.16880.018*
H18B0.54270.75630.14000.018*
C190.5566 (3)0.86876 (12)0.09454 (9)0.0147 (4)
H19A0.64020.84890.06060.018*
H19B0.59550.92450.10690.018*
C200.5197 (3)0.91447 (11)0.24330 (10)0.0168 (4)
H20A0.45180.92390.28330.025*
H20B0.50570.96170.21460.025*
H20C0.64840.90680.25350.025*
C210.4437 (3)0.76507 (11)0.25864 (9)0.0136 (4)
H210.43140.71390.23250.016*
C220.2839 (3)0.76640 (11)0.30481 (9)0.0139 (4)
C230.1435 (3)0.81574 (12)0.29524 (9)0.0150 (4)
H230.05020.81610.32690.018*
C240.1219 (3)0.87123 (12)0.23765 (9)0.0151 (4)
H24A0.14610.92830.25090.018*
H24B−0.00470.86820.22200.018*
C250.6225 (3)0.75728 (12)0.29622 (10)0.0182 (4)
H25A0.72520.75430.26560.022*
H25B0.63970.80600.32390.022*
C260.6192 (3)0.68067 (12)0.33802 (10)0.0191 (4)
H26A0.59930.63210.31040.023*
H26B0.73770.67420.35990.023*
C270.4700 (3)0.68582 (11)0.38820 (9)0.0168 (4)
H270.46580.63250.41180.020*
C280.2819 (3)0.70122 (11)0.35883 (9)0.0156 (4)
C290.1487 (3)0.72131 (13)0.41332 (9)0.0199 (4)
H29A0.17240.77660.42940.030*
H29B0.16410.68200.44860.030*
H29C0.02430.71820.39690.030*
C300.2190 (3)0.62008 (12)0.32797 (10)0.0215 (4)
H30A0.30000.60590.29220.032*
H30B0.09500.62630.31170.032*
H30C0.22210.57660.36050.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0198 (8)0.0148 (7)0.0332 (8)0.0020 (6)−0.0087 (7)0.0031 (6)
O20.0224 (8)0.0151 (6)0.0198 (7)−0.0031 (6)−0.0050 (6)0.0014 (5)
O30.0293 (9)0.0174 (7)0.0190 (7)0.0024 (7)−0.0108 (7)−0.0029 (6)
C10.0152 (10)0.0161 (9)0.0121 (8)0.0021 (8)0.0016 (8)0.0006 (7)
C20.0123 (9)0.0140 (8)0.0130 (9)0.0006 (7)−0.0012 (8)0.0005 (7)
C30.0186 (10)0.0184 (9)0.0134 (9)0.0001 (8)−0.0033 (8)−0.0014 (7)
C40.0216 (11)0.0284 (11)0.0126 (9)0.0043 (9)−0.0013 (9)0.0004 (8)
C50.0208 (11)0.0254 (10)0.0128 (9)0.0072 (9)0.0044 (9)0.0035 (8)
C60.0184 (10)0.0223 (10)0.0136 (9)0.0065 (9)0.0025 (8)0.0030 (8)
C70.0119 (9)0.0146 (9)0.0121 (8)0.0012 (7)0.0002 (7)0.0005 (7)
C80.0181 (11)0.0348 (12)0.0273 (11)−0.0002 (10)0.0018 (9)0.0123 (10)
C90.0379 (15)0.0426 (14)0.0165 (10)0.0175 (12)0.0082 (10)0.0050 (10)
C100.0106 (9)0.0128 (8)0.0119 (8)0.0012 (7)0.0012 (7)0.0009 (7)
C110.0175 (10)0.0141 (9)0.0160 (9)0.0010 (8)0.0010 (8)−0.0008 (7)
C120.0111 (9)0.0126 (8)0.0112 (8)0.0006 (7)−0.0005 (7)0.0001 (6)
C130.0120 (9)0.0170 (9)0.0155 (9)0.0012 (8)0.0008 (8)0.0034 (7)
C140.0131 (10)0.0195 (9)0.0190 (9)−0.0007 (8)−0.0017 (8)0.0045 (8)
C150.0166 (10)0.0142 (9)0.0144 (8)0.0014 (8)−0.0006 (8)0.0004 (7)
C160.0114 (9)0.0105 (8)0.0129 (8)−0.0003 (7)0.0009 (7)0.0016 (6)
C170.0115 (9)0.0135 (9)0.0128 (9)0.0009 (7)0.0001 (7)0.0018 (7)
C180.0116 (10)0.0172 (9)0.0151 (9)0.0023 (8)0.0009 (7)0.0031 (7)
C190.0128 (10)0.0167 (9)0.0146 (9)0.0005 (8)0.0008 (8)0.0014 (7)
C200.0169 (10)0.0160 (9)0.0175 (9)−0.0023 (8)−0.0021 (8)0.0013 (7)
C210.0147 (10)0.0128 (9)0.0134 (9)0.0008 (7)−0.0001 (7)0.0007 (7)
C220.0168 (10)0.0136 (8)0.0114 (8)−0.0035 (7)−0.0014 (8)−0.0003 (7)
C230.0141 (10)0.0187 (9)0.0122 (8)−0.0008 (8)0.0021 (8)−0.0002 (7)
C240.0121 (10)0.0184 (9)0.0150 (9)0.0025 (8)0.0015 (8)0.0025 (7)
C250.0152 (10)0.0188 (10)0.0205 (10)0.0013 (8)−0.0003 (8)0.0053 (8)
C260.0206 (11)0.0184 (10)0.0183 (9)0.0033 (9)−0.0030 (9)0.0032 (8)
C270.0245 (11)0.0126 (9)0.0133 (9)0.0000 (8)−0.0028 (8)0.0001 (7)
C280.0198 (10)0.0137 (9)0.0131 (9)−0.0019 (8)−0.0007 (8)−0.0002 (7)
C290.0225 (11)0.0236 (10)0.0136 (9)−0.0015 (9)0.0011 (8)0.0038 (8)
C300.0281 (12)0.0192 (10)0.0172 (9)−0.0063 (9)−0.0039 (9)0.0020 (8)

Geometric parameters (Å, °)

O1—C11.334 (2)C15—H15A0.9800
O1—H10.85 (1)C15—H15B0.9800
O2—C11.208 (2)C15—H15C0.9800
O3—C271.450 (2)C16—C241.532 (3)
O3—H30.84 (1)C16—C171.555 (3)
C1—C21.552 (3)C16—H161.0000
C2—C31.553 (3)C17—C181.538 (3)
C2—C141.571 (3)C17—C201.542 (3)
C2—C71.573 (3)C17—C211.560 (2)
C3—C41.521 (3)C18—C191.525 (2)
C3—H3A0.9900C18—H18A0.9900
C3—H3B0.9900C18—H18B0.9900
C4—C51.557 (3)C19—H19A0.9900
C4—H4A0.9900C19—H19B0.9900
C4—H4B0.9900C20—H20A0.9800
C5—C91.532 (3)C20—H20B0.9800
C5—C81.531 (3)C20—H20C0.9800
C5—C61.536 (3)C21—C221.518 (3)
C6—C71.546 (3)C21—C251.536 (3)
C6—H6A0.9900C21—H211.0000
C6—H6B0.9900C22—C231.328 (3)
C7—C101.567 (2)C22—C281.545 (2)
C7—H71.0000C23—C241.507 (2)
C8—H8A0.9800C23—H230.9500
C8—H8B0.9800C24—H24A0.9900
C8—H8C0.9800C24—H24B0.9900
C9—H9A0.9800C25—C261.523 (3)
C9—H9B0.9800C25—H25A0.9900
C9—H9C0.9800C25—H25B0.9900
C10—C191.541 (3)C26—C271.516 (3)
C10—C111.545 (3)C26—H26A0.9900
C10—C121.562 (3)C26—H26B0.9900
C11—H11A0.9800C27—C281.535 (3)
C11—H11B0.9800C27—H271.0000
C11—H11C0.9800C28—C291.532 (3)
C12—C151.542 (3)C28—C301.544 (3)
C12—C131.544 (3)C29—H29A0.9800
C12—C161.575 (2)C29—H29B0.9800
C13—C141.549 (3)C29—H29C0.9800
C13—H13A0.9900C30—H30A0.9800
C13—H13B0.9900C30—H30B0.9800
C14—H14A0.9900C30—H30C0.9800
C14—H14B0.9900
C1—O1—H1110 (2)H15A—C15—H15C109.5
C27—O3—H3105.5 (19)H15B—C15—H15C109.5
O2—C1—O1121.87 (17)C24—C16—C17109.75 (15)
O2—C1—C2126.19 (18)C24—C16—C12114.01 (15)
O1—C1—C2111.93 (17)C17—C16—C12116.04 (15)
C1—C2—C3105.10 (15)C24—C16—H16105.3
C1—C2—C14108.63 (16)C17—C16—H16105.3
C3—C2—C14107.14 (16)C12—C16—H16105.3
C1—C2—C7109.60 (16)C18—C17—C20110.12 (16)
C3—C2—C7109.74 (16)C18—C17—C16108.48 (15)
C14—C2—C7116.04 (15)C20—C17—C16113.35 (16)
C4—C3—C2112.22 (16)C18—C17—C21107.73 (15)
C4—C3—H3A109.2C20—C17—C21109.15 (15)
C2—C3—H3A109.2C16—C17—C21107.84 (15)
C4—C3—H3B109.2C19—C18—C17113.81 (15)
C2—C3—H3B109.2C19—C18—H18A108.8
H3A—C3—H3B107.9C17—C18—H18A108.8
C3—C4—C5113.42 (16)C19—C18—H18B108.8
C3—C4—H4A108.9C17—C18—H18B108.8
C5—C4—H4A108.9H18A—C18—H18B107.7
C3—C4—H4B108.9C18—C19—C10113.18 (16)
C5—C4—H4B108.9C18—C19—H19A108.9
H4A—C4—H4B107.7C10—C19—H19A108.9
C9—C5—C8108.03 (19)C18—C19—H19B108.9
C9—C5—C6108.00 (16)C10—C19—H19B108.9
C8—C5—C6110.83 (17)H19A—C19—H19B107.8
C9—C5—C4109.59 (18)C17—C20—H20A109.5
C8—C5—C4111.19 (17)C17—C20—H20B109.5
C6—C5—C4109.13 (17)H20A—C20—H20B109.5
C5—C6—C7116.03 (16)C17—C20—H20C109.5
C5—C6—H6A108.3H20A—C20—H20C109.5
C7—C6—H6A108.3H20B—C20—H20C109.5
C5—C6—H6B108.3C22—C21—C25110.42 (15)
C7—C6—H6B108.3C22—C21—C17114.20 (15)
H6A—C6—H6B107.4C25—C21—C17112.50 (16)
C6—C7—C10110.77 (15)C22—C21—H21106.4
C6—C7—C2111.23 (15)C25—C21—H21106.4
C10—C7—C2114.71 (15)C17—C21—H21106.4
C6—C7—H7106.5C23—C22—C21121.36 (16)
C10—C7—H7106.5C23—C22—C28121.35 (18)
C2—C7—H7106.5C21—C22—C28116.93 (16)
C5—C8—H8A109.5C22—C23—C24124.52 (18)
C5—C8—H8B109.5C22—C23—H23117.7
H8A—C8—H8B109.5C24—C23—H23117.7
C5—C8—H8C109.5C23—C24—C16111.90 (16)
H8A—C8—H8C109.5C23—C24—H24A109.2
H8B—C8—H8C109.5C16—C24—H24A109.2
C5—C9—H9A109.5C23—C24—H24B109.2
C5—C9—H9B109.5C16—C24—H24B109.2
H9A—C9—H9B109.5H24A—C24—H24B107.9
C5—C9—H9C109.5C26—C25—C21110.02 (17)
H9A—C9—H9C109.5C26—C25—H25A109.7
H9B—C9—H9C109.5C21—C25—H25A109.7
C19—C10—C11108.97 (16)C26—C25—H25B109.7
C19—C10—C12108.72 (14)C21—C25—H25B109.7
C11—C10—C12110.67 (16)H25A—C25—H25B108.2
C19—C10—C7107.78 (15)C27—C26—C25110.80 (17)
C11—C10—C7110.03 (15)C27—C26—H26A109.5
C12—C10—C7110.60 (14)C25—C26—H26A109.5
C10—C11—H11A109.5C27—C26—H26B109.5
C10—C11—H11B109.5C25—C26—H26B109.5
H11A—C11—H11B109.5H26A—C26—H26B108.1
C10—C11—H11C109.5O3—C27—C26109.29 (17)
H11A—C11—H11C109.5O3—C27—C28110.14 (16)
H11B—C11—H11C109.5C26—C27—C28113.18 (16)
C15—C12—C13105.88 (16)O3—C27—H27108.0
C15—C12—C10111.64 (15)C26—C27—H27108.0
C13—C12—C10107.79 (14)C28—C27—H27108.0
C15—C12—C16111.95 (14)C29—C28—C27108.85 (15)
C13—C12—C16109.17 (15)C29—C28—C30107.23 (17)
C10—C12—C16110.22 (14)C27—C28—C30107.11 (16)
C12—C13—C14115.06 (16)C29—C28—C22113.01 (16)
C12—C13—H13A108.5C27—C28—C22113.06 (16)
C14—C13—H13A108.5C30—C28—C22107.25 (15)
C12—C13—H13B108.5C28—C29—H29A109.5
C14—C13—H13B108.5C28—C29—H29B109.5
H13A—C13—H13B107.5H29A—C29—H29B109.5
C13—C14—C2120.34 (17)C28—C29—H29C109.5
C13—C14—H14A107.2H29A—C29—H29C109.5
C2—C14—H14A107.2H29B—C29—H29C109.5
C13—C14—H14B107.2C28—C30—H30A109.5
C2—C14—H14B107.2C28—C30—H30B109.5
H14A—C14—H14B106.9H30A—C30—H30B109.5
C12—C15—H15A109.5C28—C30—H30C109.5
C12—C15—H15B109.5H30A—C30—H30C109.5
H15A—C15—H15B109.5H30B—C30—H30C109.5
C12—C15—H15C109.5
O2—C1—C2—C3−128.3 (2)C15—C12—C16—C17−72.0 (2)
O1—C1—C2—C350.5 (2)C13—C12—C16—C17171.15 (15)
O2—C1—C2—C14117.3 (2)C10—C12—C16—C1752.9 (2)
O1—C1—C2—C14−63.9 (2)C24—C16—C17—C18179.31 (15)
O2—C1—C2—C7−10.4 (3)C12—C16—C17—C18−49.6 (2)
O1—C1—C2—C7168.37 (15)C24—C16—C17—C20−58.05 (19)
C1—C2—C3—C459.0 (2)C12—C16—C17—C2072.99 (19)
C14—C2—C3—C4174.41 (16)C24—C16—C17—C2162.89 (19)
C7—C2—C3—C4−58.8 (2)C12—C16—C17—C21−166.06 (14)
C2—C3—C4—C554.0 (2)C20—C17—C18—C19−73.7 (2)
C3—C4—C5—C9119.69 (19)C16—C17—C18—C1950.8 (2)
C3—C4—C5—C8−120.95 (19)C21—C17—C18—C19167.33 (16)
C3—C4—C5—C61.6 (2)C17—C18—C19—C10−58.2 (2)
C9—C5—C6—C7−172.55 (19)C11—C10—C19—C18−62.8 (2)
C8—C5—C6—C769.3 (2)C12—C10—C19—C1857.9 (2)
C4—C5—C6—C7−53.5 (2)C7—C10—C19—C18177.82 (15)
C5—C6—C7—C10176.81 (17)C18—C17—C21—C22−161.11 (16)
C5—C6—C7—C248.0 (2)C20—C17—C21—C2279.3 (2)
C1—C2—C7—C6−106.48 (18)C16—C17—C21—C22−44.2 (2)
C3—C2—C7—C68.5 (2)C18—C17—C21—C2572.02 (19)
C14—C2—C7—C6130.06 (17)C20—C17—C21—C25−47.5 (2)
C1—C2—C7—C10126.83 (16)C16—C17—C21—C25−171.08 (15)
C3—C2—C7—C10−118.23 (16)C25—C21—C22—C23140.08 (18)
C14—C2—C7—C103.4 (2)C17—C21—C22—C2312.1 (2)
C6—C7—C10—C1967.88 (19)C25—C21—C22—C28−46.6 (2)
C2—C7—C10—C19−165.19 (16)C17—C21—C22—C28−174.56 (16)
C6—C7—C10—C11−50.8 (2)C21—C22—C23—C243.2 (3)
C2—C7—C10—C1176.1 (2)C28—C22—C23—C24−169.77 (18)
C6—C7—C10—C12−173.40 (16)C22—C23—C24—C1615.8 (3)
C2—C7—C10—C12−46.5 (2)C17—C16—C24—C23−48.9 (2)
C19—C10—C12—C1571.33 (18)C12—C16—C24—C23178.98 (15)
C11—C10—C12—C15−169.02 (15)C22—C21—C25—C2657.1 (2)
C7—C10—C12—C15−46.8 (2)C17—C21—C25—C26−173.99 (16)
C19—C10—C12—C13−172.80 (15)C21—C25—C26—C27−62.7 (2)
C11—C10—C12—C13−53.15 (19)C25—C26—C27—O3−67.6 (2)
C7—C10—C12—C1369.05 (18)C25—C26—C27—C2855.6 (2)
C19—C10—C12—C16−53.74 (19)O3—C27—C28—C29−46.8 (2)
C11—C10—C12—C1665.91 (19)C26—C27—C28—C29−169.46 (16)
C7—C10—C12—C16−171.90 (15)O3—C27—C28—C30−162.41 (16)
C15—C12—C13—C1472.33 (19)C26—C27—C28—C3074.91 (19)
C10—C12—C13—C14−47.3 (2)O3—C27—C28—C2279.67 (19)
C16—C12—C13—C14−166.99 (15)C26—C27—C28—C22−43.0 (2)
C12—C13—C14—C25.1 (3)C23—C22—C28—C29−22.9 (3)
C1—C2—C14—C13−106.01 (19)C21—C22—C28—C29163.82 (16)
C3—C2—C14—C13140.93 (18)C23—C22—C28—C27−147.09 (18)
C7—C2—C14—C1318.0 (2)C21—C22—C28—C2739.6 (2)
C15—C12—C16—C2457.0 (2)C23—C22—C28—C3095.1 (2)
C13—C12—C16—C24−59.8 (2)C21—C22—C28—C30−78.2 (2)
C10—C12—C16—C24−178.05 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.85 (1)1.90 (1)2.731 (2)167 (3)
O3—H3···O2ii0.84 (1)2.36 (2)3.080 (2)144 (2)

Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2325).

References

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  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
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  • Jiang, Z.-H., Zhou, R.-H., Sasuda, K. & Ageta, H. (1995). Phytochemistry, 40, 219–224.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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