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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2381.
Published online 2010 August 21. doi:  10.1107/S1600536810032101
PMCID: PMC3007948

rac-(3aR,6aR)-(E)-Methyl 2-(3a-methyl­perhydro­furo[3,2-b]furan-2-yl­idene)acetate

Abstract

The constitution and relative configuration at the stereogenic centres and stereochemistry of the C—C double bond formed during PdII-catalysed domino reaction was established by X-ray analysis of the title compound, C10H14O4. The asymmetric unit contains two mol­ecules.

Related literature

The title compound was prepared from 4-methyl­pent-4-en-1,3-diol (Breit & Zahn, 2001 [triangle]) by a modified procedure for carbonyl­ation of alkene-3-ol (Semmelhack & Epa, 1993 [triangle]).

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Object name is e-66-o2381-scheme1.jpg

Experimental

Crystal data

  • C10H14O4
  • M r = 198.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2381-efi1.jpg
  • a = 12.159 (1) Å
  • b = 5.8100 (3) Å
  • c = 28.509 (1) Å
  • β = 101.51 (1)°
  • V = 1973.5 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.84 × 0.36 × 0.12 mm

Data collection

  • Oxford Diffraction Gemini R CCD diffractometer
  • Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010 [triangle]); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995 [triangle])] T min = 0.941, T max = 0.988
  • 59312 measured reflections
  • 4033 independent reflections
  • 3571 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.091
  • S = 1.05
  • 4025 reflections
  • 254 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: enCIFer (Allen et al., 2004 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032101/bv2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032101/bv2142Isup2.hkl

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

Acknowledgments

The authors thank the Grant Agency of Slovak Republic, Grant Nos. VEGA 1/0817/08 and VEGA 1/0115/10, and the Structural Funds, Inter­reg IIIA, for financial support in purchasing the diffractometer.

supplementary crystallographic information

Comment

As a part of our long term program directed towards the application of palladium(II)-catalysed oxycarbonylation of unsaturated polyols in the natural product synthesis we studied the domino Pd(II)-promoted reactions. The title compound, [(I): alternative name: (±)-(1'R, 5'R)-(E)-methyl 2-(5'-methyl-2',6'-dioxabicyclo[3.3.0]octa-3'-ylidene) acetate] represents a product of the first diastereoselective domino intramolecular Wacker-type cyclization - Heck reaction - cyclization of 4-methylpent-4-en-1,3-diol with methyl acrylate. The asymmetric unit contains two molecules of the same chirality (Z' = 2), but as the space group is centrosymmetric, both enantiomers are present in the unit cell.

Experimental

The title compound was prepared from 4-methylpent-4-en-1,3-diol (Breit and Zahn, 2001) by a modified procedure for carbonylation of alkene-3-ol (Semmelhack and Epa, 1993). A mixture of 4-methylpent-4-en-1,3-diol (200 mg, 1.70 mmol, 1 equivalent) and CuCl freshly recrystallized (170 mg, 1.70 mmol, 1 equivalent) in dry DMF (7 ml) was stirred at r.t for 10 min. under oxygen atmosphere (balloon). The methyl acrylate (0.8 ml, 8.60 mmol, 5 equivalents) and palladium acetate (39 mg, 0.17 mmol, 0.1 equivalent) were then added. The mixture was stirred for 56 h, then diluted by ethyl acetate (100 ml). The organic solution was washed three times with sat. aq. ammonium chloride solution, driedover anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, ethyl acetate-hexane-3:1, Rf 0.73). The title compound was slowly crystallized from hexane to give white crystals [m.p. 65–67 °C].1H NMR (300 MHz, Varian, CDCl3): δ(p.p.m.) = 1.43 (s, 3H, CH3); 2.17 (m, 2H, H-8'); 2.96 3.64 (2xd, 2H, J=19.7, H-4'); 3.69–4.04 (m, 6H, H-1', H-7', OCH3); 4.66 (d, 1H, J= 6.3 Hz, H-2). 13C NMR (75 MHz, CDCl3): δ(p.p.m.) = 22.7 (q, CH3), 32.7 (t, C-8'), 44.2 (t, C-4'), 50.8 (q, OCH3), 66.9 (t, C-7'), 87.7 (s, C-5'), 89.9 (d, C-1'), 91.3 (d, C-2), 168.7 (s, C-1), 175.7 (d, C-3'). IČ, film: ν(cm-1) = 3479 (w), 2975 (m), 2951 (m), 2874 (w), 1789 (w), 1705 (s), 1645 (s), 1437 (s), 1410 (w), 1364 (s), 1317 (m), 1274 (m), 1193 (s), 1148 (s), 1106 (s), 1093 (s), 1039 (s), 1010 (m), 978 (m), 950 (w), 933 (w), 900 (w), 871 (w), 822 (m), 734 (w), 592 (w) [cm-1]

Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms (C—H = 0.93, 0.96 and 0.97 Å) and Uiso(H) values were taken to be equal to 1.2 Ueq(C) all H atoms.

Figures

Fig. 1.
The numbering scheme of title compound. Displacement ellipsoids are shown at the 50% probability level.
Fig. 2.
Synthesis of rac-(3aR, 6aR)-(E)-methyl 2-(3a-methyl-tetrahydrofuro [3,2-b]furan-2-ylidene)acetate.

Crystal data

C10H14O4F(000) = 848
Mr = 198.21Dx = 1.334 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 35551 reflections
a = 12.159 (1) Åθ = 3.6–29.5°
b = 5.8100 (3) ŵ = 0.10 mm1
c = 28.509 (1) ÅT = 293 K
β = 101.51 (1)°Block, colorless
V = 1973.5 (2) Å30.84 × 0.36 × 0.12 mm
Z = 8

Data collection

Oxford Diffraction Gemini R CCD diffractometer4033 independent reflections
Radiation source: Enhance (Mo) X-ray Source3571 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 10.4340 pixels mm-1θmax = 26.4°, θmin = 3.6°
Rotation method data acquisition using ω and [var phi] scansh = −15→15
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010); analytical numeric absorption correction using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]k = −7→7
Tmin = 0.941, Tmax = 0.988l = −35→35
59312 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.091w = 1/[σ2(Fo2) + (0.0375P)2 + 1.2579P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4025 reflectionsΔρmax = 0.32 e Å3
254 parametersΔρmin = −0.22 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0031 (7)

Special details

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.62 (release 16-03-2010 CrysAlis171 .NET) (compiled Mar 16 2010,16:26:05) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.independent reflections were 4033, 7 inconsistent equivalents, 4025 were used in the refinement

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

xyzUiso*/Ueq
C20.35925 (10)0.2368 (2)0.34753 (4)0.0173 (3)
C30.35197 (10)0.4998 (2)0.34359 (4)0.0174 (3)
H3A0.40740.56380.32650.021*
C40.36899 (10)0.5847 (2)0.39470 (4)0.0195 (3)
H4B0.33190.73110.39670.023*
H4A0.44810.59970.40890.023*
C50.31418 (11)0.3932 (2)0.41825 (4)0.0212 (3)
H5B0.34750.38290.45210.025*
H5A0.23440.42140.41490.025*
C70.18323 (10)0.3541 (2)0.30141 (4)0.0177 (3)
C80.26323 (10)0.1555 (2)0.30792 (4)0.0192 (3)
H8B0.28970.12370.27860.023*
H8A0.22820.01800.31750.023*
C90.47359 (10)0.1376 (2)0.34558 (5)0.0212 (3)
H9C0.4713−0.02700.34840.025*
H9B0.52860.19890.37150.025*
H9A0.49330.17790.31570.025*
C100.07393 (10)0.3673 (2)0.28094 (4)0.0197 (3)
H10A0.03790.50890.27990.024*
C110.01014 (10)0.1674 (2)0.26033 (4)0.0189 (3)
C14−0.16945 (12)0.0392 (3)0.22261 (6)0.0306 (3)
H14C−0.24460.09460.21180.037*
H14B−0.1693−0.07910.24610.037*
H14A−0.1416−0.02250.19600.037*
C160.86595 (10)0.9608 (2)0.38508 (4)0.0190 (3)
C170.96259 (11)1.0068 (2)0.42723 (4)0.0200 (3)
H17A0.95891.16010.44120.024*
C181.06680 (11)0.9721 (2)0.40691 (5)0.0247 (3)
H18B1.13030.92770.43160.030*
H18A1.08571.10980.39100.030*
C191.03089 (11)0.7781 (3)0.37159 (5)0.0255 (3)
H19B1.07140.78550.34560.031*
H19A1.04520.62990.38730.031*
C210.85362 (10)0.7177 (2)0.45081 (4)0.0177 (3)
C220.78158 (10)0.8268 (2)0.40773 (4)0.0206 (3)
H22B0.72640.92900.41690.025*
H22A0.74310.71110.38590.025*
C230.81782 (12)1.1718 (2)0.35705 (5)0.0270 (3)
H23C0.75811.12630.33140.032*
H23B0.87561.24670.34420.032*
H23A0.78931.27600.37790.032*
C240.83161 (10)0.5412 (2)0.47796 (4)0.0190 (3)
H24A0.88720.49030.50310.023*
C250.72309 (11)0.4285 (2)0.46889 (4)0.0201 (3)
C280.61577 (12)0.1322 (3)0.49483 (5)0.0279 (3)
H28C0.62340.00620.51700.033*
H28B0.59130.07510.46280.033*
H28A0.56150.23950.50210.033*
O10.33343 (8)0.18484 (15)0.39400 (3)0.0210 (2)
O60.23724 (7)0.54910 (15)0.31945 (3)0.0197 (2)
O120.04472 (8)−0.02687 (16)0.25726 (3)0.0231 (2)
O13−0.09856 (7)0.22621 (17)0.24354 (3)0.0248 (2)
O150.91270 (7)0.81006 (17)0.35392 (3)0.0232 (2)
O200.95504 (7)0.82156 (16)0.46110 (3)0.0205 (2)
O260.64051 (8)0.48260 (19)0.43955 (4)0.0318 (3)
O270.72256 (7)0.24603 (16)0.49859 (3)0.0239 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C20.0185 (6)0.0160 (6)0.0180 (6)−0.0016 (5)0.0051 (5)−0.0007 (5)
C30.0155 (6)0.0168 (6)0.0198 (6)−0.0014 (5)0.0032 (4)0.0003 (5)
C40.0191 (6)0.0178 (6)0.0204 (6)0.0004 (5)0.0012 (5)−0.0026 (5)
C50.0257 (6)0.0192 (6)0.0193 (6)0.0023 (5)0.0059 (5)−0.0015 (5)
C70.0227 (6)0.0163 (6)0.0147 (5)−0.0028 (5)0.0050 (5)−0.0003 (5)
C80.0192 (6)0.0168 (6)0.0217 (6)−0.0007 (5)0.0041 (5)−0.0019 (5)
C90.0190 (6)0.0199 (6)0.0246 (6)0.0001 (5)0.0044 (5)−0.0008 (5)
C100.0214 (6)0.0181 (6)0.0189 (6)0.0016 (5)0.0024 (5)−0.0004 (5)
C110.0195 (6)0.0226 (6)0.0150 (5)−0.0006 (5)0.0041 (5)0.0002 (5)
C140.0212 (7)0.0321 (8)0.0356 (8)−0.0056 (6)−0.0011 (6)−0.0088 (6)
C160.0199 (6)0.0196 (6)0.0176 (6)0.0025 (5)0.0041 (5)−0.0012 (5)
C170.0246 (6)0.0179 (6)0.0168 (6)−0.0026 (5)0.0022 (5)0.0013 (5)
C180.0198 (6)0.0295 (7)0.0242 (6)−0.0041 (5)0.0029 (5)0.0051 (6)
C190.0200 (6)0.0307 (7)0.0265 (7)0.0047 (5)0.0062 (5)0.0011 (6)
C210.0163 (6)0.0210 (6)0.0160 (6)0.0008 (5)0.0032 (4)−0.0031 (5)
C220.0178 (6)0.0242 (6)0.0195 (6)0.0029 (5)0.0029 (5)0.0025 (5)
C230.0314 (7)0.0261 (7)0.0234 (6)0.0069 (6)0.0052 (5)0.0065 (6)
C240.0166 (6)0.0231 (6)0.0165 (6)0.0007 (5)0.0012 (4)0.0012 (5)
C250.0206 (6)0.0233 (6)0.0171 (6)−0.0001 (5)0.0055 (5)−0.0002 (5)
C280.0256 (7)0.0306 (7)0.0281 (7)−0.0105 (6)0.0070 (5)0.0010 (6)
O10.0282 (5)0.0169 (4)0.0198 (4)−0.0007 (4)0.0090 (4)0.0002 (3)
O60.0196 (4)0.0157 (4)0.0214 (4)−0.0003 (3)−0.0013 (3)−0.0007 (3)
O120.0236 (5)0.0209 (5)0.0239 (5)−0.0012 (4)0.0029 (4)−0.0036 (4)
O130.0181 (4)0.0262 (5)0.0274 (5)−0.0016 (4)−0.0014 (4)−0.0060 (4)
O150.0203 (5)0.0283 (5)0.0209 (4)0.0026 (4)0.0038 (4)−0.0062 (4)
O200.0195 (4)0.0232 (5)0.0175 (4)−0.0042 (4)0.0003 (3)0.0037 (4)
O260.0184 (5)0.0438 (6)0.0305 (5)−0.0051 (4)−0.0022 (4)0.0121 (5)
O270.0211 (5)0.0237 (5)0.0264 (5)−0.0046 (4)0.0033 (4)0.0048 (4)

Geometric parameters (Å, °)

C2—O11.4529 (14)C16—O151.4424 (15)
C2—C91.5164 (17)C16—C231.5157 (18)
C2—C81.5283 (17)C16—C171.5274 (17)
C2—C31.5333 (17)C16—C221.5297 (17)
C3—O61.4555 (14)C17—O201.4610 (15)
C3—C41.5131 (17)C17—C181.5082 (18)
C3—H3A0.9800C17—H17A0.9800
C4—C51.5203 (18)C18—C191.517 (2)
C4—H4B0.9700C18—H18B0.9700
C4—H4A0.9700C18—H18A0.9700
C5—O11.4359 (15)C19—O151.4369 (15)
C5—H5B0.9700C19—H19B0.9700
C5—H5A0.9700C19—H19A0.9700
C7—C101.3428 (18)C21—C241.3433 (18)
C7—O61.3581 (15)C21—O201.3516 (15)
C7—C81.4967 (17)C21—C221.4994 (17)
C8—H8B0.9700C22—H22B0.9700
C8—H8A0.9700C22—H22A0.9700
C9—H9C0.9600C23—H23C0.9600
C9—H9B0.9600C23—H23B0.9600
C9—H9A0.9600C23—H23A0.9600
C10—C111.4537 (17)C24—C251.4494 (17)
C10—H10A0.9300C24—H24A0.9300
C11—O121.2139 (16)C25—O261.2131 (16)
C11—O131.3565 (15)C25—O271.3576 (16)
C14—O131.4403 (16)C28—O271.4420 (15)
C14—H14C0.9600C28—H28C0.9600
C14—H14B0.9600C28—H28B0.9600
C14—H14A0.9600C28—H28A0.9600
O1—C2—C9108.71 (10)O15—C16—C22109.33 (10)
O1—C2—C8109.72 (10)C23—C16—C22114.41 (11)
C9—C2—C8115.22 (10)C17—C16—C22103.44 (10)
O1—C2—C3104.73 (10)O20—C17—C18108.89 (10)
C9—C2—C3114.60 (10)O20—C17—C16104.54 (10)
C8—C2—C3103.27 (10)C18—C17—C16104.34 (10)
O6—C3—C4108.98 (10)O20—C17—H17A112.8
O6—C3—C2105.46 (9)C18—C17—H17A112.8
C4—C3—C2105.03 (10)C16—C17—H17A112.8
O6—C3—H3A112.3C17—C18—C19101.64 (10)
C4—C3—H3A112.3C17—C18—H18B111.4
C2—C3—H3A112.3C19—C18—H18B111.4
C3—C4—C5101.48 (10)C17—C18—H18A111.4
C3—C4—H4B111.5C19—C18—H18A111.4
C5—C4—H4B111.5H18B—C18—H18A109.3
C3—C4—H4A111.5O15—C19—C18105.78 (11)
C5—C4—H4A111.5O15—C19—H19B110.6
H4B—C4—H4A109.3C18—C19—H19B110.6
O1—C5—C4106.05 (10)O15—C19—H19A110.6
O1—C5—H5B110.5C18—C19—H19A110.6
C4—C5—H5B110.5H19B—C19—H19A108.7
O1—C5—H5A110.5C24—C21—O20119.59 (11)
C4—C5—H5A110.5C24—C21—C22130.07 (11)
H5B—C5—H5A108.7O20—C21—C22110.34 (11)
C10—C7—O6118.61 (11)C21—C22—C16103.27 (10)
C10—C7—C8131.31 (12)C21—C22—H22B111.1
O6—C7—C8110.06 (10)C16—C22—H22B111.1
C7—C8—C2103.59 (10)C21—C22—H22A111.1
C7—C8—H8B111.0C16—C22—H22A111.1
C2—C8—H8B111.0H22B—C22—H22A109.1
C7—C8—H8A111.0C16—C23—H23C109.5
C2—C8—H8A111.0C16—C23—H23B109.5
H8B—C8—H8A109.0H23C—C23—H23B109.5
C2—C9—H9C109.5C16—C23—H23A109.5
C2—C9—H9B109.5H23C—C23—H23A109.5
H9C—C9—H9B109.5H23B—C23—H23A109.5
C2—C9—H9A109.5C21—C24—C25121.40 (11)
H9C—C9—H9A109.5C21—C24—H24A119.3
H9B—C9—H9A109.5C25—C24—H24A119.3
C7—C10—C11122.15 (12)O26—C25—O27121.75 (12)
C7—C10—H10A118.9O26—C25—C24127.21 (12)
C11—C10—H10A118.9O27—C25—C24111.04 (11)
O12—C11—O13122.40 (12)O27—C28—H28C109.5
O12—C11—C10127.40 (12)O27—C28—H28B109.5
O13—C11—C10110.20 (11)H28C—C28—H28B109.5
O13—C14—H14C109.5O27—C28—H28A109.5
O13—C14—H14B109.5H28C—C28—H28A109.5
H14C—C14—H14B109.5H28B—C28—H28A109.5
O13—C14—H14A109.5C5—O1—C2110.45 (9)
H14C—C14—H14A109.5C7—O6—C3111.12 (9)
H14B—C14—H14A109.5C11—O13—C14114.63 (11)
O15—C16—C23108.93 (10)C19—O15—C16110.61 (9)
O15—C16—C17104.78 (10)C21—O20—C17111.13 (9)
C23—C16—C17115.38 (11)C25—O27—C28115.34 (10)
O1—C2—C3—O6−92.66 (10)O20—C21—C22—C1616.47 (13)
C9—C2—C3—O6148.3 (1)O15—C16—C22—C2185.89 (11)
C8—C2—C3—O622.21 (12)C23—C16—C22—C21−151.64 (11)
O1—C2—C3—C422.4 (1)C17—C16—C22—C21−25.31 (12)
C9—C2—C3—C4−96.62 (12)O20—C21—C24—C25178.52 (11)
C8—C2—C3—C4137.27 (10)C22—C21—C24—C25−2.3 (2)
O6—C3—C4—C579.11 (11)C21—C24—C25—O26−4.7 (2)
C2—C3—C4—C5−33.49 (12)C21—C24—C25—O27175.91 (11)
C3—C4—C5—O133.07 (12)C4—C5—O1—C2−20.25 (13)
C10—C7—C8—C2−161.49 (13)C9—C2—O1—C5121.59 (11)
O6—C7—C8—C219.87 (13)C8—C2—O1—C5−111.59 (11)
O1—C2—C8—C786.28 (11)C3—C2—O1—C5−1.33 (13)
C9—C2—C8—C7−150.66 (10)C10—C7—O6—C3175.36 (11)
C3—C2—C8—C7−24.94 (12)C8—C7—O6—C3−5.81 (13)
O6—C7—C10—C11179.36 (11)C4—C3—O6—C7−123.13 (11)
C8—C7—C10—C110.8 (2)C2—C3—O6—C7−10.82 (13)
C7—C10—C11—O12−2.6 (2)O12—C11—O13—C140.98 (17)
C7—C10—C11—O13177.98 (11)C10—C11—O13—C14−179.57 (11)
O15—C16—C17—O20−88.79 (11)C18—C19—O15—C16−17.45 (14)
C23—C16—C17—O20151.4 (1)C23—C16—O15—C19119.00 (12)
C22—C16—C17—O2025.73 (12)C17—C16—O15—C19−4.99 (13)
O15—C16—C17—C1825.5 (1)C22—C16—O15—C19−115.31 (11)
C23—C16—C17—C18−94.26 (13)C24—C21—O20—C17179.38 (11)
C22—C16—C17—C18140.03 (11)C22—C21—O20—C170.07 (14)
O20—C17—C18—C1976.14 (12)C18—C17—O20—C21−127.75 (11)
C16—C17—C18—C19−35.04 (13)C16—C17—O20—C21−16.70 (13)
C17—C18—C19—O1532.43 (13)O26—C25—O27—C28−3.84 (18)
C24—C21—C22—C16−162.75 (13)C24—C25—O27—C28175.63 (11)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2142).

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