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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1448.
Published online 2009 May 29. doi:  10.1107/S1600536809019710
PMCID: PMC2969586

8,14-Secogammacera-7,14(27)-diene-3,21-dione–8,14-secogammacera-7,14-diene-3,21-dione (1.5/0.5) from the bark of Lansium domesticum Corr.

Abstract

The components of the title cocrystal, 1.5C30H40O2·0.5C30H40O2, each have two tetra­hydro­deca­lin-type fused rings connected through an ethyl­ene fragment [R—CH2—CH2R′ torsion angles: 158.1 (7) ° in the major component and 157.5 (6)° in the minor component]. The structure is a non-merohedral twin, with a minor twin component of 26%. The exocyclic double-bonded C atom of the major component of the cocrystal is disordered over two sites of equal occupancy.

Related literature

For another compound from the seeds of this plant, see: Mayanti et al. (2009 [triangle]). For related compounds, see: Habaguchi et al. (1968 [triangle]); Kiang et al. (1967 [triangle]); Nishizawa et al. (1982 [triangle], 1983 [triangle], 1984 [triangle]); Tanaka et al. (2002 [triangle]). For the procedure to TwinRotMat the diffraction data, see: Spek (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1448-scheme1.jpg

Experimental

Crystal data

  • 1.5C30H46O4·0.5C30H46O4
  • M r = 877.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1448-efi1.jpg
  • a = 8.4522 (2) Å
  • b = 11.7144 (2) Å
  • c = 14.1292 (3) Å
  • α = 107.484 (1)°
  • β = 90.249 (1)°
  • γ = 104.871 (1)°
  • V = 1284.60 (5) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 118 K
  • 0.42 × 0.08 × 0.06 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 9450 measured reflections
  • 4459 independent reflections
  • 3954 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.084
  • wR(F 2) = 0.249
  • S = 1.12
  • 4459 reflections
  • 603 parameters
  • 66 restraints
  • H-atom parameters constrained
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.41 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]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019710/tk2453sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019710/tk2453Isup2.hkl

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

Acknowledgments

This work was supported by the Directorate of Higher Education, Indonesia, the University of Padjadjaran (I-MHERE Project) and the Science Fund (12–02-03–2063).

supplementary crystallographic information

Experimental

Lansium domesticum Corr (Meliaceae) was collected in Cililin, Bandung, Indonesia, in 2006. The plant was identified by the staff at the Department of Biology, Padjadjaran University. The dried and milled bark of L.domesticum (3 kg) was extracted exhaustively by methanol at room temperature. The methanol extract (200 g) was partitioned between n-hexane and 10% aqueous methanol to give an n-hexane soluble fraction (70 g); 11 g of the n-hexane extract was subjected to column chromatography on silica gel 60 by using a step gradient of n-hexane and ethyl acetate (8:2) followed by separation with preparative thin layer chromatography on silica gel. The co-crystal was eluted with an ethyl acetate: n-hexane (9:1) mixture; onoceradienedione (33 mg) was obtained as a powder along with several crystals when the solvent was allowed to evaporate.

The formulation of the co-crystal, i.e., a 75% component having an excocyclic double bond and a 25% component having an endocyclic double bond, was established by NMR spectroscopic analysis.

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 U(H) set to 1.2–1.5U(C).

The structure is a non-merohdral twin. The twin law, as given by PLATON (Spek, 2003), is (1.010 0.030 0.013, -0.670 - 1.010 - 0.004, 0.000 0.000 - 1.000), which lowered the R1 index from 10.4% to 8.40%. A total of X Friedel pairs were merged.

The exocyclic double-bonded carbon atom of major component of the co-crystal is disordered over two sites (the ring carbon is the carbon atom at the 14 position according to IUPAC nomenclature); the occupancy was arbitrarily set as 50:50. The disorder required the ring carbon at 13 position to be disordered. The exocyclic carbon-carbon double-bond distance was restrained to 1.35±0.01 Å (in the umprimed fragment) and the exocyclic carbon-carbon single bond was restrained to 1.54±0.01 Å (in the primed fragment). The endocylic single- and double-bond distances were similarly restrained. The anisotropic displacement parameters of the primed atoms were set to those of the umprimed ones, and these were restrained to be nearly isotropic.

The disorder also affected the two methyl groups at carbon atom adjacent to the carbonyl group at the 21 position. For the four carbon atoms connected to this atom, the 1,2-related distances were restrained to 1.54±0.01 Å and the 1,3-related ones to 2.51±0.01 Å. The anisotropic displacement parameters of all five atoms were restrained to be nearly isotropic. Finally, the distance between the H46b and H57d atoms was restrained to 2.00±0.01 Å; this additional restraint was applied to the C57 methyl group.

The assignment of the atoms was guided by NMR spectral measurements. The ratio of the two chemically similar molecules were furnished by proton NMR spectral integration.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the major component of co-crystal C30H40O2–C30H40O2 (1.5/0.5) (with the exocyclic double bond at the 14 position) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Thermal ellipsoid plot (Barbour, 2001) of the minor component of co-crystal C30H40O2–C30H40O2 (1.5/0.5) (with the endocyclic double bond at the 13 position) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. ...

Crystal data

1.5C30H46O4·0.5C30H46O4Z = 1
Mr = 877.34F(000) = 484
Triclinic, P1Dx = 1.134 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4522 (2) ÅCell parameters from 4429 reflections
b = 11.7144 (2) Åθ = 2.5–28.2°
c = 14.1292 (3) ŵ = 0.07 mm1
α = 107.484 (1)°T = 118 K
β = 90.249 (1)°Irregular fragment, colorless
γ = 104.871 (1)°0.42 × 0.08 × 0.06 mm
V = 1284.60 (5) Å3

Data collection

Bruker SMART APEX diffractometer3954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
graphiteθmax = 25.0°, θmin = 1.5°
ω scansh = −10→10
9450 measured reflectionsk = −13→13
4459 independent reflectionsl = −16→16

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.084w = 1/[σ2(Fo2) + (0.1369P)2 + 1.7886P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.249(Δ/σ)max = 0.001
S = 1.12Δρmax = 0.51 e Å3
4459 reflectionsΔρmin = −0.41 e Å3
603 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
66 restraintsExtinction coefficient: 0.034 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Friedel pairs were merged
Secondary atom site location: difference Fourier map

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

xyzUiso*/UeqOcc. (<1)
O10.4978 (7)0.4989 (6)0.5001 (4)0.0358 (14)
O20.8406 (8)0.2884 (7)−0.2153 (5)0.0456 (16)
O30.6627 (8)−0.0020 (6)0.8831 (4)0.0416 (15)
O40.2865 (10)0.1987 (9)0.2699 (6)0.065 (2)
C10.4206 (10)0.5309 (7)0.4436 (5)0.0263 (16)
C20.2372 (10)0.5138 (7)0.4471 (5)0.0270 (16)
C30.1500 (9)0.4964 (7)0.3425 (5)0.0252 (16)
H30.12750.40550.30650.030*
C40.2476 (10)0.5601 (7)0.2708 (5)0.0247 (16)
C50.4184 (9)0.5382 (7)0.2690 (5)0.0269 (16)
H5A0.40770.44790.24320.032*
H5B0.48260.57800.22340.032*
C60.5098 (9)0.5913 (8)0.3728 (6)0.0292 (17)
H6A0.62110.57850.36870.035*
H6B0.52190.68190.39810.035*
C70.2225 (11)0.6324 (8)0.5296 (6)0.0343 (19)
H7A0.27990.63890.59220.051*
H7B0.10630.62700.53900.051*
H7C0.27200.70600.50970.051*
C80.1579 (11)0.4018 (8)0.4801 (6)0.0360 (19)
H8A0.19220.41960.55060.054*
H8B0.19240.32960.44010.054*
H8C0.03800.38390.47100.054*
C90.2587 (11)0.6997 (7)0.3003 (6)0.0306 (17)
H9A0.29030.73800.37190.046*
H9B0.15160.71060.28450.046*
H9C0.34130.73950.26330.046*
C10−0.0194 (10)0.5195 (8)0.3499 (5)0.0312 (18)
H10A−0.08760.46500.38460.037*
H10B−0.00820.60680.39030.037*
C11−0.1049 (10)0.4950 (9)0.2495 (6)0.036 (2)
H11−0.21870.49020.24520.044*
C12−0.0271 (10)0.4793 (8)0.1648 (6)0.0304 (18)
C130.1536 (9)0.4923 (7)0.1643 (5)0.0223 (15)
H130.16650.40590.14370.027*
C14−0.1296 (11)0.4461 (11)0.0675 (7)0.048 (2)
H14A−0.24630.42870.07910.072*
H14B−0.10860.37230.02000.072*
H14C−0.10020.51570.04030.072*
C150.2347 (10)0.5529 (7)0.0862 (5)0.0256 (16)
H15A0.17470.61220.07800.031*
H15B0.34920.60080.11210.031*
C160.2363 (9)0.4589 (7)−0.0161 (5)0.0252 (16)
H16A0.25530.3830−0.00650.030*
H16B0.12720.4351−0.05330.030*
C170.3681 (8)0.5090 (6)−0.0784 (5)0.0199 (14)
H170.46910.5536−0.03150.024*
C180.3311 (10)0.6044 (7)−0.1215 (5)0.0263 (16)
C190.4661 (11)0.6623 (8)−0.1720 (7)0.0348 (18)
H19A0.55980.7138−0.12220.042*
H19B0.42870.7176−0.20260.042*
C200.5233 (11)0.5650 (7)−0.2525 (6)0.0313 (18)
H20A0.61980.6065−0.28100.038*
H20B0.43440.5202−0.30680.038*
C210.5690 (9)0.4728 (6)−0.2079 (5)0.0206 (14)
H210.64850.5257−0.14900.025*
C220.6670 (9)0.3905 (7)−0.2771 (5)0.0243 (16)
C230.7036 (10)0.3031 (7)−0.2234 (6)0.0290 (17)
C240.5618 (10)0.2319 (7)−0.1828 (6)0.0296 (17)
H24A0.60200.1844−0.14530.035*
H24B0.48330.1719−0.23870.035*
C250.4741 (9)0.3192 (7)−0.1143 (5)0.0231 (15)
H25A0.54910.3712−0.05420.028*
H25B0.37710.2687−0.09250.028*
C260.4176 (9)0.4046 (6)−0.1630 (5)0.0209 (15)
C270.1888 (11)0.6331 (9)−0.1156 (7)0.040 (2)
H27A0.17130.6928−0.14460.048*
H27B0.10440.5940−0.08250.048*
C280.5751 (10)0.3063 (7)−0.3786 (5)0.0282 (17)
H28A0.64970.2649−0.41960.042*
H28B0.53620.3569−0.41260.042*
H28C0.48100.2437−0.36800.042*
C290.8282 (10)0.4723 (8)−0.2964 (7)0.038 (2)
H29A0.89870.4200−0.32850.056*
H29B0.88430.5312−0.23300.056*
H29C0.80480.5182−0.34000.056*
C300.2681 (9)0.3305 (6)−0.2379 (5)0.0207 (14)
H30A0.29290.2578−0.28480.031*
H30B0.24180.3832−0.27460.031*
H30C0.17390.3029−0.20230.031*
C310.7311 (10)−0.0360 (7)0.8087 (6)0.0261 (16)
C320.9146 (9)−0.0262 (7)0.8147 (6)0.0229 (15)
C330.9937 (8)−0.0113 (6)0.7161 (5)0.0186 (14)
H331.02100.07990.72560.022*
C340.8886 (9)−0.0729 (6)0.6156 (5)0.0193 (14)
C350.7205 (9)−0.0454 (7)0.6294 (5)0.0246 (16)
H35A0.73570.04560.64950.030*
H35B0.6513−0.08340.56530.030*
C360.6330 (9)−0.0967 (8)0.7086 (6)0.0289 (17)
H36A0.5230−0.08130.71360.035*
H36B0.6177−0.18770.68870.035*
C371.0002 (12)0.0875 (8)0.9011 (6)0.037 (2)
H37A0.96180.07600.96380.055*
H37B0.97490.16120.89280.055*
H37C1.11930.09870.90240.055*
C380.9304 (11)−0.1429 (7)0.8389 (6)0.0303 (17)
H38A0.8772−0.14710.89970.045*
H38B1.0469−0.13850.84890.045*
H38C0.8771−0.21720.78350.045*
C390.8652 (9)−0.2147 (6)0.5766 (5)0.0226 (15)
H39A0.8354−0.25020.63070.034*
H39B0.9678−0.23160.55220.034*
H39C0.7775−0.25230.52210.034*
C401.1577 (8)−0.0420 (7)0.7075 (5)0.0225 (15)
H40A1.23220.01060.76760.027*
H40B1.1412−0.13000.70420.027*
C411.2368 (8)−0.0216 (7)0.6165 (5)0.0229 (15)
H411.3492−0.02070.61190.027*
C421.1577 (8)−0.0047 (6)0.5418 (5)0.0203 (14)
C430.9770 (8)−0.0119 (6)0.5391 (5)0.0175 (14)
H430.96900.07580.56030.021*
C441.2528 (10)0.0256 (8)0.4583 (6)0.0319 (17)
H44A1.36930.03330.47260.048*
H44B1.24040.10420.45260.048*
H44C1.2104−0.04100.39560.048*
C450.8865 (8)−0.0753 (6)0.4324 (5)0.0203 (14)
H45A0.9389−0.14000.39530.024*
H45B0.7712−0.11760.43840.024*
C460.8863 (10)0.0133 (8)0.3714 (6)0.0316 (18)
H46A0.87660.09370.41670.038*
H46B0.99280.02930.34210.038*
C470.7467 (9)−0.0368 (7)0.2873 (5)0.0215 (15)
H470.6471−0.07790.31490.026*0.50
H47'0.6473−0.07660.31580.026*0.50
C480.786 (4)−0.142 (2)0.198 (3)0.032 (3)0.50
C490.677 (4)−0.165 (2)0.1035 (18)0.032 (4)0.50
H49A0.7501−0.17180.04890.038*0.50
H49B0.6007−0.24870.09080.038*0.50
C48'0.763 (3)−0.129 (3)0.198 (3)0.032 (3)0.50
C49'0.646 (3)−0.189 (2)0.1219 (18)0.032 (4)0.50
H49'0.6088−0.27720.09330.038*0.50
C500.5790 (12)−0.0908 (9)0.0873 (6)0.042 (2)
H50A0.4733−0.14670.05140.050*0.50
H50B0.6343−0.04540.04250.050*0.50
H50C0.6627−0.04790.05160.050*0.50
H50D0.4783−0.13420.04130.050*0.50
C510.5411 (9)0.0035 (6)0.1783 (5)0.0297 (17)
H510.4662−0.04890.21280.036*
C520.4376 (9)0.0838 (7)0.1550 (5)0.040 (2)
C530.4158 (10)0.1782 (7)0.2527 (5)0.0352 (19)
C540.5677 (11)0.2462 (9)0.3207 (6)0.0370 (19)
H54A0.53930.30110.38260.044*
H54B0.64430.29940.28850.044*
C550.6537 (9)0.1592 (7)0.3472 (5)0.0258 (16)
H55A0.58020.11030.38380.031*
H55B0.75410.20920.39190.031*
C560.7009 (9)0.0698 (6)0.2548 (5)0.0212 (15)
C570.844 (2)−0.2388 (15)0.1999 (12)0.035 (3)0.50
H57A0.8162−0.31360.14540.042*0.50
H57B0.9128−0.23190.25580.042*0.50
C57'0.935 (2)−0.1516 (16)0.1936 (12)0.035 (3)0.50
H57C0.9524−0.18770.24560.053*0.50
H57D1.0186−0.07260.20440.053*0.50
H57E0.9425−0.20910.12820.053*0.50
C580.5217 (12)0.1574 (8)0.0869 (6)0.053 (3)
H58A0.62610.21500.12080.080*
H58B0.45000.20450.07150.080*
H58C0.54240.09970.02490.080*
C590.2678 (11)0.0000 (10)0.1045 (8)0.081 (4)
H59A0.20210.05130.08960.121*
H59B0.2115−0.04350.14940.121*
H59C0.2820−0.06090.04250.121*
C600.8467 (11)0.1366 (8)0.2113 (7)0.0333 (18)
H60A0.82040.20540.19470.050*
H60B0.87090.07820.15090.050*
H60C0.94270.16920.26030.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.036 (3)0.052 (4)0.030 (3)0.023 (3)−0.003 (2)0.018 (3)
O20.025 (3)0.066 (4)0.061 (4)0.024 (3)0.012 (3)0.032 (3)
O30.048 (4)0.057 (4)0.037 (3)0.028 (3)0.025 (3)0.027 (3)
O40.055 (5)0.100 (6)0.053 (4)0.052 (4)0.009 (4)0.018 (4)
C10.034 (4)0.022 (4)0.022 (4)0.014 (3)−0.001 (3)0.001 (3)
C20.028 (4)0.032 (4)0.022 (4)0.015 (3)−0.002 (3)0.003 (3)
C30.024 (4)0.034 (4)0.018 (3)0.013 (3)0.003 (3)0.006 (3)
C40.037 (4)0.024 (4)0.012 (3)0.008 (3)−0.005 (3)0.005 (3)
C50.025 (4)0.034 (4)0.022 (4)0.009 (3)0.002 (3)0.008 (3)
C60.017 (4)0.041 (4)0.029 (4)0.003 (3)0.001 (3)0.014 (3)
C70.047 (5)0.038 (5)0.019 (4)0.021 (4)0.002 (3)0.002 (3)
C80.041 (5)0.047 (5)0.024 (4)0.014 (4)0.000 (3)0.017 (4)
C90.039 (5)0.029 (4)0.025 (4)0.015 (3)−0.002 (3)0.006 (3)
C100.032 (4)0.049 (5)0.018 (4)0.016 (4)0.007 (3)0.013 (3)
C110.018 (4)0.067 (6)0.029 (4)0.015 (4)0.005 (3)0.018 (4)
C120.025 (4)0.044 (5)0.023 (4)0.010 (4)0.001 (3)0.012 (3)
C130.021 (4)0.031 (4)0.014 (3)0.007 (3)0.002 (3)0.006 (3)
C140.029 (5)0.086 (8)0.028 (4)0.011 (5)−0.001 (4)0.019 (5)
C150.030 (4)0.026 (4)0.021 (4)0.008 (3)0.003 (3)0.008 (3)
C160.028 (4)0.028 (4)0.016 (3)0.002 (3)0.003 (3)0.006 (3)
C170.017 (3)0.025 (4)0.015 (3)0.003 (3)−0.001 (3)0.004 (3)
C180.035 (4)0.024 (4)0.021 (4)0.012 (3)0.001 (3)0.004 (3)
C190.037 (5)0.030 (4)0.037 (4)0.008 (3)0.010 (4)0.011 (3)
C200.039 (5)0.024 (4)0.031 (4)0.004 (3)0.010 (3)0.013 (3)
C210.021 (4)0.021 (3)0.015 (3)−0.001 (3)0.001 (3)0.004 (3)
C220.022 (4)0.024 (4)0.025 (4)−0.001 (3)0.009 (3)0.010 (3)
C230.027 (4)0.032 (4)0.026 (4)0.011 (3)0.002 (3)0.002 (3)
C240.028 (4)0.031 (4)0.036 (4)0.009 (3)0.007 (3)0.017 (3)
C250.024 (4)0.029 (4)0.018 (3)0.005 (3)0.003 (3)0.011 (3)
C260.027 (4)0.018 (3)0.013 (3)0.002 (3)−0.001 (3)0.003 (3)
C270.035 (5)0.059 (6)0.041 (5)0.021 (4)0.011 (4)0.030 (4)
C280.039 (5)0.029 (4)0.019 (3)0.015 (3)0.006 (3)0.006 (3)
C290.025 (4)0.039 (5)0.050 (5)0.007 (4)0.019 (4)0.016 (4)
C300.020 (4)0.019 (3)0.021 (3)0.003 (3)0.003 (3)0.006 (3)
C310.036 (4)0.026 (4)0.028 (4)0.015 (3)0.014 (3)0.019 (3)
C320.022 (4)0.020 (3)0.030 (4)0.006 (3)0.006 (3)0.011 (3)
C330.017 (3)0.020 (3)0.018 (3)0.004 (3)0.003 (3)0.005 (3)
C340.024 (4)0.023 (4)0.017 (3)0.014 (3)0.001 (3)0.008 (3)
C350.026 (4)0.032 (4)0.021 (4)0.014 (3)0.003 (3)0.011 (3)
C360.018 (4)0.043 (4)0.035 (4)0.013 (3)0.007 (3)0.022 (4)
C370.051 (5)0.033 (4)0.021 (4)0.003 (4)0.006 (4)0.009 (3)
C380.040 (5)0.026 (4)0.031 (4)0.012 (3)0.001 (3)0.016 (3)
C390.023 (4)0.023 (4)0.020 (3)0.004 (3)−0.002 (3)0.006 (3)
C400.013 (3)0.035 (4)0.023 (4)0.010 (3)−0.001 (3)0.009 (3)
C410.012 (3)0.031 (4)0.022 (4)0.002 (3)−0.001 (3)0.004 (3)
C420.016 (3)0.019 (3)0.022 (3)0.003 (3)0.005 (3)0.003 (3)
C430.017 (3)0.015 (3)0.021 (3)0.005 (3)0.005 (3)0.007 (3)
C440.027 (4)0.037 (4)0.031 (4)0.004 (3)0.006 (3)0.014 (3)
C450.017 (3)0.024 (4)0.023 (4)0.007 (3)0.004 (3)0.011 (3)
C460.028 (4)0.038 (4)0.034 (4)0.000 (3)0.003 (3)0.026 (4)
C470.022 (4)0.030 (4)0.016 (3)0.006 (3)0.006 (3)0.012 (3)
C480.055 (7)0.035 (6)0.026 (4)0.034 (4)0.011 (5)0.018 (4)
C490.038 (8)0.022 (8)0.031 (8)0.002 (6)0.002 (6)0.005 (5)
C48'0.055 (7)0.035 (6)0.026 (4)0.034 (4)0.011 (5)0.018 (4)
C49'0.038 (8)0.022 (8)0.031 (8)0.002 (6)0.002 (6)0.005 (5)
C500.051 (5)0.052 (5)0.020 (4)0.018 (4)−0.006 (4)0.004 (4)
C510.031 (4)0.034 (4)0.021 (3)0.008 (3)−0.001 (3)0.007 (3)
C520.043 (5)0.059 (5)0.026 (4)0.025 (4)−0.001 (3)0.013 (4)
C530.036 (4)0.051 (5)0.034 (4)0.027 (4)0.009 (3)0.023 (4)
C540.038 (5)0.046 (5)0.031 (4)0.023 (4)0.009 (4)0.007 (4)
C550.021 (4)0.034 (4)0.022 (4)0.009 (3)0.004 (3)0.006 (3)
C560.025 (4)0.025 (4)0.016 (3)0.009 (3)0.007 (3)0.008 (3)
C570.044 (6)0.035 (5)0.027 (5)0.016 (5)0.007 (5)0.005 (4)
C57'0.044 (6)0.035 (5)0.027 (5)0.016 (5)0.007 (5)0.005 (4)
C580.067 (5)0.069 (5)0.043 (4)0.043 (4)0.009 (4)0.025 (4)
C590.063 (8)0.092 (9)0.075 (8)0.039 (7)−0.043 (7)−0.005 (7)
C600.038 (5)0.040 (5)0.041 (4)0.027 (4)0.015 (4)0.028 (4)

Geometric parameters (Å, °)

O1—C11.227 (9)C32—C331.585 (10)
O2—C231.224 (10)C33—C401.516 (9)
O3—C311.212 (9)C33—C341.540 (9)
O4—C531.189 (10)C33—H331.0000
C1—C61.493 (11)C34—C351.537 (10)
C1—C21.514 (11)C34—C391.543 (10)
C2—C81.520 (12)C34—C431.560 (9)
C2—C71.556 (10)C35—C361.532 (10)
C2—C31.581 (10)C35—H35A0.9900
C3—C101.522 (11)C35—H35B0.9900
C3—C41.552 (10)C36—H36A0.9900
C3—H31.0000C36—H36B0.9900
C4—C51.529 (11)C37—H37A0.9800
C4—C91.539 (11)C37—H37B0.9800
C4—C131.573 (9)C37—H37C0.9800
C5—C61.526 (10)C38—H38A0.9800
C5—H5A0.9900C38—H38B0.9800
C5—H5B0.9900C38—H38C0.9800
C6—H6A0.9900C39—H39A0.9800
C6—H6B0.9900C39—H39B0.9800
C7—H7A0.9800C39—H39C0.9800
C7—H7B0.9800C40—C411.506 (10)
C7—H7C0.9800C40—H40A0.9900
C8—H8A0.9800C40—H40B0.9900
C8—H8B0.9800C41—C421.337 (10)
C8—H8C0.9800C41—H410.9500
C9—H9A0.9800C42—C431.508 (9)
C9—H9B0.9800C42—C441.508 (10)
C9—H9C0.9800C43—C451.560 (10)
C10—C111.502 (11)C43—H431.0000
C10—H10A0.9900C44—H44A0.9800
C10—H10B0.9900C44—H44B0.9800
C11—C121.355 (11)C44—H44C0.9800
C11—H110.9500C45—C461.537 (10)
C12—C131.496 (11)C45—H45A0.9900
C12—C141.512 (11)C45—H45B0.9900
C13—C151.555 (10)C46—C471.537 (10)
C13—H131.0000C46—H46A0.9900
C14—H14A0.9800C46—H46B0.9900
C14—H14B0.9800C47—C48'1.43 (3)
C14—H14C0.9800C47—C481.59 (3)
C15—C161.535 (10)C47—C561.585 (9)
C15—H15A0.9900C47—H471.0000
C15—H15B0.9900C47—H47'1.0000
C16—C171.531 (10)C48—C571.352 (10)
C16—H16A0.9900C48—C491.534 (10)
C16—H16B0.9900C49—C501.40 (3)
C17—C181.518 (10)C49—H49A0.9900
C17—C261.577 (9)C49—H49B0.9900
C17—H171.0000C48'—C49'1.342 (10)
C18—C271.326 (12)C48'—C57'1.540 (10)
C18—C191.474 (11)C49'—C501.60 (3)
C19—C201.528 (11)C49'—H49'0.9500
C19—H19A0.9900C50—C511.518 (11)
C19—H19B0.9900C50—H50A0.9900
C20—C211.528 (10)C50—H50B0.9900
C20—H20A0.9900C50—H50C0.9900
C20—H20B0.9900C50—H50D0.9900
C21—C221.556 (10)C51—C521.538 (7)
C21—C261.570 (9)C51—C561.594 (10)
C21—H211.0000C51—H511.0000
C22—C291.529 (10)C52—C531.534 (7)
C22—C231.533 (11)C52—C581.538 (8)
C22—C281.542 (10)C52—C591.542 (8)
C23—C241.496 (11)C53—C541.487 (12)
C24—C251.527 (11)C54—C551.521 (11)
C24—H24A0.9900C54—H54A0.9900
C24—H24B0.9900C54—H54B0.9900
C25—C261.537 (10)C55—C561.535 (9)
C25—H25A0.9900C55—H55A0.9900
C25—H25B0.9900C55—H55B0.9900
C26—C301.531 (9)C56—C601.519 (11)
C27—H27A0.9500C57—H57A0.9500
C27—H27B0.9500C57—H57B0.9500
C28—H28A0.9800C57'—H57C0.9800
C28—H28B0.9800C57'—H57D0.9800
C28—H28C0.9800C57'—H57E0.9800
C29—H29A0.9800C58—H58A0.9800
C29—H29B0.9800C58—H58B0.9800
C29—H29C0.9800C58—H58C0.9800
C30—H30A0.9800C59—H59A0.9800
C30—H30B0.9800C59—H59B0.9800
C30—H30C0.9800C59—H59C0.9800
C31—C361.508 (11)C60—H60A0.9800
C31—C321.525 (11)C60—H60B0.9800
C32—C371.519 (11)C60—H60C0.9800
C32—C381.542 (10)
O1—C1—C6119.5 (7)C35—C34—C33108.1 (6)
O1—C1—C2120.9 (7)C35—C34—C39109.8 (6)
C6—C1—C2119.6 (6)C33—C34—C39112.5 (5)
C1—C2—C8110.8 (7)C35—C34—C43109.2 (5)
C1—C2—C7104.1 (6)C33—C34—C43107.7 (6)
C8—C2—C7108.0 (7)C39—C34—C43109.5 (5)
C1—C2—C3112.0 (6)C36—C35—C34111.2 (6)
C8—C2—C3108.7 (6)C36—C35—H35A109.4
C7—C2—C3113.1 (6)C34—C35—H35A109.4
C10—C3—C4110.2 (6)C36—C35—H35B109.4
C10—C3—C2113.0 (6)C34—C35—H35B109.4
C4—C3—C2119.1 (6)H35A—C35—H35B108.0
C10—C3—H3104.3C31—C36—C35110.8 (6)
C4—C3—H3104.3C31—C36—H36A109.5
C2—C3—H3104.3C35—C36—H36A109.5
C5—C4—C9111.2 (6)C31—C36—H36B109.5
C5—C4—C3108.1 (6)C35—C36—H36B109.5
C9—C4—C3112.5 (6)H36A—C36—H36B108.1
C5—C4—C13108.8 (6)C32—C37—H37A109.5
C9—C4—C13109.5 (6)C32—C37—H37B109.5
C3—C4—C13106.5 (6)H37A—C37—H37B109.5
C6—C5—C4111.3 (6)C32—C37—H37C109.5
C6—C5—H5A109.4H37A—C37—H37C109.5
C4—C5—H5A109.4H37B—C37—H37C109.5
C6—C5—H5B109.4C32—C38—H38A109.5
C4—C5—H5B109.4C32—C38—H38B109.5
H5A—C5—H5B108.0H38A—C38—H38B109.5
C1—C6—C5111.4 (6)C32—C38—H38C109.5
C1—C6—H6A109.3H38A—C38—H38C109.5
C5—C6—H6A109.3H38B—C38—H38C109.5
C1—C6—H6B109.3C34—C39—H39A109.5
C5—C6—H6B109.3C34—C39—H39B109.5
H6A—C6—H6B108.0H39A—C39—H39B109.5
C2—C7—H7A109.5C34—C39—H39C109.5
C2—C7—H7B109.5H39A—C39—H39C109.5
H7A—C7—H7B109.5H39B—C39—H39C109.5
C2—C7—H7C109.5C41—C40—C33111.9 (6)
H7A—C7—H7C109.5C41—C40—H40A109.2
H7B—C7—H7C109.5C33—C40—H40A109.2
C2—C8—H8A109.5C41—C40—H40B109.2
C2—C8—H8B109.5C33—C40—H40B109.2
H8A—C8—H8B109.5H40A—C40—H40B107.9
C2—C8—H8C109.5C42—C41—C40123.7 (6)
H8A—C8—H8C109.5C42—C41—H41118.2
H8B—C8—H8C109.5C40—C41—H41118.2
C4—C9—H9A109.5C41—C42—C43122.3 (6)
C4—C9—H9B109.5C41—C42—C44119.1 (6)
H9A—C9—H9B109.5C43—C42—C44118.6 (6)
C4—C9—H9C109.5C42—C43—C45113.1 (6)
H9A—C9—H9C109.5C42—C43—C34112.2 (6)
H9B—C9—H9C109.5C45—C43—C34111.5 (5)
C11—C10—C3112.3 (6)C42—C43—H43106.5
C11—C10—H10A109.1C45—C43—H43106.5
C3—C10—H10A109.1C34—C43—H43106.5
C11—C10—H10B109.1C42—C44—H44A109.5
C3—C10—H10B109.1C42—C44—H44B109.5
H10A—C10—H10B107.9H44A—C44—H44B109.5
C12—C11—C10123.0 (7)C42—C44—H44C109.5
C12—C11—H11118.5H44A—C44—H44C109.5
C10—C11—H11118.5H44B—C44—H44C109.5
C11—C12—C13122.7 (7)C46—C45—C43114.8 (6)
C11—C12—C14117.8 (7)C46—C45—H45A108.6
C13—C12—C14119.5 (7)C43—C45—H45A108.6
C12—C13—C15113.2 (6)C46—C45—H45B108.6
C12—C13—C4112.6 (6)C43—C45—H45B108.6
C15—C13—C4111.5 (6)H45A—C45—H45B107.5
C12—C13—H13106.3C47—C46—C45113.6 (6)
C15—C13—H13106.3C47—C46—H46A108.8
C4—C13—H13106.3C45—C46—H46A108.8
C12—C14—H14A109.5C47—C46—H46B108.8
C12—C14—H14B109.5C45—C46—H46B108.8
H14A—C14—H14B109.5H46A—C46—H46B107.7
C12—C14—H14C109.5C48'—C47—C46118.7 (9)
H14A—C14—H14C109.5C46—C47—C48110.2 (10)
H14B—C14—H14C109.5C48'—C47—C56106.5 (13)
C16—C15—C13113.7 (6)C46—C47—C56112.9 (6)
C16—C15—H15A108.8C48—C47—C56113.8 (11)
C13—C15—H15A108.8C48'—C47—H47105.0
C16—C15—H15B108.8C46—C47—H47106.4
C13—C15—H15B108.8C48—C47—H47106.4
H15A—C15—H15B107.7C56—C47—H47106.4
C17—C16—C15113.2 (6)C48'—C47—H47'105.9
C17—C16—H16A108.9C46—C47—H47'105.9
C15—C16—H16A108.9C48—C47—H47'107.4
C17—C16—H16B108.9C56—C47—H47'105.9
C15—C16—H16B108.9C57—C48—C49115 (2)
H16A—C16—H16B107.8C57—C48—C47129 (3)
C18—C17—C16114.8 (6)C49—C48—C47110.1 (15)
C18—C17—C26109.8 (5)C50—C49—C48128 (2)
C16—C17—C26114.0 (6)C50—C49—H49A105.4
C18—C17—H17105.8C48—C49—H49A105.4
C16—C17—H17105.8C50—C49—H49B105.4
C26—C17—H17105.8C48—C49—H49B105.4
C27—C18—C19122.2 (7)H49A—C49—H49B106.0
C27—C18—C17123.3 (7)C49'—C48'—C47125 (2)
C19—C18—C17114.5 (7)C49'—C48'—C57'122 (3)
C18—C19—C20111.7 (7)C47—C48'—C57'113.0 (17)
C18—C19—H19A109.3C48'—C49'—C50109.4 (19)
C20—C19—H19A109.3C48'—C49'—H49'125.3
C18—C19—H19B109.3C50—C49'—H49'125.3
C20—C19—H19B109.3C49—C50—C51117.3 (12)
H19A—C19—H19B107.9C51—C50—C49'109.2 (11)
C19—C20—C21109.9 (6)C49—C50—H50A108.0
C19—C20—H20A109.7C51—C50—H50A108.0
C21—C20—H20A109.7C49'—C50—H50A98.8
C19—C20—H20B109.7C49—C50—H50B108.0
C21—C20—H20B109.7C51—C50—H50B108.0
H20A—C20—H20B108.2C49'—C50—H50B124.4
C20—C21—C22113.2 (6)H50A—C50—H50B107.2
C20—C21—C26110.8 (6)C49—C50—H50C93.3
C22—C21—C26117.2 (5)C51—C50—H50C109.8
C20—C21—H21104.8C49'—C50—H50C109.8
C22—C21—H21104.8H50A—C50—H50C120.4
C26—C21—H21104.8C49—C50—H50D116.6
C29—C22—C23109.7 (7)C51—C50—H50D109.8
C29—C22—C28108.2 (6)C49'—C50—H50D109.8
C23—C22—C28106.1 (6)H50C—C50—H50D108.3
C29—C22—C21110.0 (6)C50—C51—C52114.6 (6)
C23—C22—C21107.4 (6)C50—C51—C56110.1 (6)
C28—C22—C21115.2 (6)C52—C51—C56118.8 (6)
O2—C23—C24120.5 (8)C50—C51—H51103.8
O2—C23—C22122.6 (7)C52—C51—H51103.8
C24—C23—C22116.9 (6)C56—C51—H51103.8
C23—C24—C25111.0 (6)C53—C52—C51108.9 (5)
C23—C24—H24A109.4C53—C52—C58107.5 (6)
C25—C24—H24A109.4C51—C52—C58111.9 (5)
C23—C24—H24B109.4C53—C52—C59109.6 (6)
C25—C24—H24B109.4C51—C52—C59109.6 (7)
H24A—C24—H24B108.0C58—C52—C59109.3 (6)
C24—C25—C26113.8 (6)O4—C53—C54122.9 (7)
C24—C25—H25A108.8O4—C53—C52121.4 (7)
C26—C25—H25A108.8C54—C53—C52115.6 (6)
C24—C25—H25B108.8C53—C54—C55112.5 (7)
C26—C25—H25B108.8C53—C54—H54A109.1
H25A—C25—H25B107.7C55—C54—H54A109.1
C30—C26—C25110.2 (5)C53—C54—H54B109.1
C30—C26—C21114.7 (5)C55—C54—H54B109.1
C25—C26—C21108.2 (6)H54A—C54—H54B107.8
C30—C26—C17109.1 (6)C54—C55—C56112.4 (6)
C25—C26—C17108.1 (5)C54—C55—H55A109.1
C21—C26—C17106.3 (5)C56—C55—H55A109.1
C18—C27—H27A120.0C54—C55—H55B109.1
C18—C27—H27B120.0C56—C55—H55B109.1
H27A—C27—H27B120.0H55A—C55—H55B107.9
C22—C28—H28A109.5C60—C56—C55111.3 (6)
C22—C28—H28B109.5C60—C56—C47109.6 (6)
H28A—C28—H28B109.5C55—C56—C47108.0 (5)
C22—C28—H28C109.5C60—C56—C51113.8 (6)
H28A—C28—H28C109.5C55—C56—C51107.9 (6)
H28B—C28—H28C109.5C47—C56—C51106.1 (5)
C22—C29—H29A109.5C48—C57—H57A120.0
C22—C29—H29B109.5C48—C57—H57B120.0
H29A—C29—H29B109.5H57A—C57—H57B120.0
C22—C29—H29C109.5C48'—C57'—H57C109.5
H29A—C29—H29C109.5C48'—C57'—H57D109.5
H29B—C29—H29C109.5H57C—C57'—H57D109.5
C26—C30—H30A109.5C48'—C57'—H57E109.5
C26—C30—H30B109.5H57C—C57'—H57E109.5
H30A—C30—H30B109.5H57D—C57'—H57E109.5
C26—C30—H30C109.5C52—C58—H58A109.5
H30A—C30—H30C109.5C52—C58—H58B109.5
H30B—C30—H30C109.5H58A—C58—H58B109.5
O3—C31—C36120.0 (7)C52—C58—H58C109.5
O3—C31—C32121.2 (7)H58A—C58—H58C109.5
C36—C31—C32118.7 (6)H58B—C58—H58C109.5
C37—C32—C31108.7 (7)C52—C59—H59A109.5
C37—C32—C38108.3 (6)C52—C59—H59B109.5
C31—C32—C38105.8 (6)H59A—C59—H59B109.5
C37—C32—C33108.2 (6)C52—C59—H59C109.5
C31—C32—C33111.9 (6)H59A—C59—H59C109.5
C38—C32—C33113.8 (6)H59B—C59—H59C109.5
C40—C33—C34109.9 (5)C56—C60—H60A109.5
C40—C33—C32112.0 (6)C56—C60—H60B109.5
C34—C33—C32119.3 (6)H60A—C60—H60B109.5
C40—C33—H33104.8C56—C60—H60C109.5
C34—C33—H33104.8H60A—C60—H60C109.5
C32—C33—H33104.8H60B—C60—H60C109.5
O1—C1—C2—C8−30.2 (10)C37—C32—C33—C34−151.3 (6)
C6—C1—C2—C8151.8 (7)C31—C32—C33—C34−31.6 (8)
O1—C1—C2—C785.7 (8)C38—C32—C33—C3488.2 (8)
C6—C1—C2—C7−92.3 (8)C40—C33—C34—C35176.9 (6)
O1—C1—C2—C3−151.7 (7)C32—C33—C34—C3545.7 (8)
C6—C1—C2—C330.3 (9)C40—C33—C34—C3955.5 (8)
C1—C2—C3—C10−162.0 (7)C32—C33—C34—C39−75.7 (8)
C8—C2—C3—C1075.2 (8)C40—C33—C34—C43−65.3 (7)
C7—C2—C3—C10−44.7 (10)C32—C33—C34—C43163.5 (6)
C1—C2—C3—C4−30.3 (9)C33—C34—C35—C36−59.7 (8)
C8—C2—C3—C4−153.0 (7)C39—C34—C35—C3663.3 (8)
C7—C2—C3—C487.1 (8)C43—C34—C35—C36−176.6 (6)
C10—C3—C4—C5178.0 (6)O3—C31—C36—C35136.2 (7)
C2—C3—C4—C545.0 (8)C32—C31—C36—C35−47.7 (9)
C10—C3—C4—C954.7 (8)C34—C35—C36—C3161.9 (8)
C2—C3—C4—C9−78.2 (8)C34—C33—C40—C4147.9 (8)
C10—C3—C4—C13−65.2 (8)C32—C33—C40—C41−177.1 (6)
C2—C3—C4—C13161.9 (6)C33—C40—C41—C42−13.5 (10)
C9—C4—C5—C664.8 (8)C40—C41—C42—C43−3.6 (11)
C3—C4—C5—C6−59.2 (8)C40—C41—C42—C44174.9 (7)
C13—C4—C5—C6−174.6 (6)C41—C42—C43—C45−141.8 (7)
O1—C1—C6—C5135.6 (7)C44—C42—C43—C4539.6 (8)
C2—C1—C6—C5−46.4 (9)C41—C42—C43—C34−14.6 (9)
C4—C5—C6—C161.1 (9)C44—C42—C43—C34166.9 (6)
C4—C3—C10—C1147.6 (9)C35—C34—C43—C42164.7 (6)
C2—C3—C10—C11−176.5 (7)C33—C34—C43—C4247.6 (7)
C3—C10—C11—C12−12.6 (13)C39—C34—C43—C42−75.0 (7)
C10—C11—C12—C13−3.6 (14)C35—C34—C43—C45−67.2 (7)
C10—C11—C12—C14175.7 (9)C33—C34—C43—C45175.7 (5)
C11—C12—C13—C15−143.3 (8)C39—C34—C43—C4553.0 (7)
C14—C12—C13—C1537.5 (11)C42—C43—C45—C46−88.7 (7)
C11—C12—C13—C4−15.7 (11)C34—C43—C45—C46143.6 (6)
C14—C12—C13—C4165.0 (8)C43—C45—C46—C47−157.6 (6)
C5—C4—C13—C12164.8 (6)C45—C46—C47—C48'−78.0 (19)
C9—C4—C13—C12−73.5 (8)C45—C46—C47—C48−75.0 (17)
C3—C4—C13—C1248.4 (8)C45—C46—C47—C56156.4 (6)
C5—C4—C13—C15−66.8 (8)C48'—C47—C48—C57−152 (21)
C9—C4—C13—C1555.0 (8)C46—C47—C48—C5745 (4)
C3—C4—C13—C15176.9 (6)C56—C47—C48—C57173 (3)
C12—C13—C15—C16−90.1 (8)C48'—C47—C48—C490(16)
C4—C13—C15—C16141.7 (7)C46—C47—C48—C49−163.3 (18)
C13—C15—C16—C17−158.1 (6)C56—C47—C48—C49−35 (3)
C15—C16—C17—C18−73.5 (8)C57—C48—C49—C50169 (2)
C15—C16—C17—C26158.6 (6)C47—C48—C49—C5013 (4)
C16—C17—C18—C27−7.1 (10)C46—C47—C48'—C49'173 (2)
C26—C17—C18—C27122.9 (8)C56—C47—C48'—C49'−58 (3)
C16—C17—C18—C19173.6 (6)C46—C47—C48'—C57'−8(3)
C26—C17—C18—C19−56.4 (8)C56—C47—C48'—C57'121 (2)
C27—C18—C19—C20−125.1 (9)C47—C48'—C49'—C5053 (4)
C17—C18—C19—C2054.2 (9)C57'—C48'—C49'—C50−126 (3)
C18—C19—C20—C21−54.6 (9)C48—C49—C50—C51−17 (3)
C19—C20—C21—C22−166.2 (6)C48—C49—C50—C49'−81 (6)
C19—C20—C21—C2659.9 (8)C48'—C49'—C50—C4974 (7)
C20—C21—C22—C2960.8 (8)C48'—C49'—C50—C51−48 (3)
C26—C21—C22—C29−168.4 (6)C49—C50—C51—C52178.4 (13)
C20—C21—C22—C23−179.8 (6)C49'—C50—C51—C52−165.9 (11)
C26—C21—C22—C23−49.0 (8)C49—C50—C51—C5641.4 (15)
C20—C21—C22—C28−61.8 (8)C49'—C50—C51—C5657.1 (12)
C26—C21—C22—C2869.0 (8)C50—C51—C52—C53−177.4 (7)
C29—C22—C23—O2−12.1 (10)C56—C51—C52—C53−44.3 (8)
C28—C22—C23—O2104.6 (9)C50—C51—C52—C58−58.7 (9)
C21—C22—C23—O2−131.6 (8)C56—C51—C52—C5874.4 (8)
C29—C22—C23—C24169.7 (7)C50—C51—C52—C5962.8 (9)
C28—C22—C23—C24−73.6 (8)C56—C51—C52—C59−164.1 (7)
C21—C22—C23—C2450.2 (8)C51—C52—C53—O4−136.3 (9)
O2—C23—C24—C25127.2 (8)C58—C52—C53—O4102.3 (9)
C22—C23—C24—C25−54.5 (9)C59—C52—C53—O4−16.4 (11)
C23—C24—C25—C2654.9 (9)C51—C52—C53—C5447.0 (9)
C24—C25—C26—C3073.9 (8)C58—C52—C53—C54−74.4 (8)
C24—C25—C26—C21−52.2 (7)C59—C52—C53—C54166.9 (8)
C24—C25—C26—C17−166.9 (6)O4—C53—C54—C55127.5 (9)
C20—C21—C26—C3059.7 (7)C52—C53—C54—C55−55.8 (9)
C22—C21—C26—C30−72.2 (8)C53—C54—C55—C5658.3 (9)
C20—C21—C26—C25−176.8 (6)C54—C55—C56—C6073.9 (8)
C22—C21—C26—C2551.3 (7)C54—C55—C56—C47−165.8 (6)
C20—C21—C26—C17−60.9 (7)C54—C55—C56—C51−51.6 (8)
C22—C21—C26—C17167.2 (6)C48'—C47—C56—C60−68.1 (13)
C18—C17—C26—C30−66.9 (7)C46—C47—C56—C6063.9 (8)
C16—C17—C26—C3063.5 (7)C48—C47—C56—C60−62.8 (15)
C18—C17—C26—C25173.2 (6)C48'—C47—C56—C55170.6 (12)
C16—C17—C26—C25−56.3 (7)C46—C47—C56—C55−57.5 (8)
C18—C17—C26—C2157.3 (7)C48—C47—C56—C55175.8 (14)
C16—C17—C26—C21−172.3 (6)C48'—C47—C56—C5155.1 (13)
O3—C31—C32—C37−32.7 (9)C46—C47—C56—C51−172.9 (6)
C36—C31—C32—C37151.3 (7)C48—C47—C56—C5160.4 (15)
O3—C31—C32—C3883.4 (8)C50—C51—C56—C6058.7 (8)
C36—C31—C32—C38−92.6 (8)C52—C51—C56—C60−76.3 (8)
O3—C31—C32—C33−152.1 (7)C50—C51—C56—C55−177.3 (6)
C36—C31—C32—C3331.9 (9)C52—C51—C56—C5547.7 (8)
C37—C32—C33—C4078.4 (8)C50—C51—C56—C47−61.9 (7)
C31—C32—C33—C40−161.9 (6)C52—C51—C56—C47163.2 (6)
C38—C32—C33—C40−42.1 (8)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2453).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Habaguchi, K., Watanabe, M., Nakadaira, Y., Nakanishi, K., Kiang, A. K. & Lim, F. L. (1968). Tetrahedron Lett.9, 3731–3734.
  • Kiang, A. K., Tan, E. L., Lim, F. Y., Habaguchi, K., Nakanishi, K., Fachan, L. & Ourisson, G. (1967). Tetrahedron Lett.8, 3571–3574.
  • Mayanti, T., Supratman, U., Mukhtar, M. R., Awang, K. & Ng, S. W. (2009). Acta Cryst. E65, o750. [PMC free article] [PubMed]
  • Nishizawa, M., Nishide, H. & Hayashi, Y. (1984). Tetrahedron Lett.25, 5071–5074.
  • Nishizawa, M., Nishide, H., Hayashi, Y. & Kosela, S. (1982). Tetrahedron Lett.23, 1349–1350.
  • Nishizawa, M., Nishide, H., Kosela, S. & Hayashi, Y. (1983). J. Org. Chem.48, 4462–4466.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Tanaka, T., Ishibaschi, M., Fujimoto, H., Okuyama, E., Koyano, T., Kowithayakorn, T., Hayashi, M. & Komiyama, K. (2002). J. Nat. Prod.65, 1709–1711. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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