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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o516.
Published online 2008 January 25. doi:  10.1107/S1600536808002055
PMCID: PMC2960447

4-Butyl-3-(3,5-dimethoxy­phen­yl)-4-meth­oxy-2-(triisopropyl­silyl)cyclopent-2-enone

Abstract

The title mol­ecule, C27H44O4Si, bears a bulky triisopropyl­silyl group. The cyclopentene ring adopts an envelope conformation; the plane of its four coplanar C atoms and the benzene ring make a dihedral angle of 73.2 (6)°.

Related literature

For related literature, see: Allen et al. (1987 [triangle]); Frontier & Collison (2005 [triangle]); Geis & Schmalz (1998 [triangle]); Roberts et al. (2002 [triangle]); Shi et al. (2005 [triangle]); Tanaka & Fu (2001 [triangle]); Li et al. (2007 [triangle], 2008 [triangle]).

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Object name is e-64-0o516-scheme1.jpg

Experimental

Crystal data

  • C27H44O4Si
  • M r = 460.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o516-efi1.jpg
  • a = 39.294 (4) Å
  • b = 8.3327 (10) Å
  • c = 29.274 (3) Å
  • β = 146.207 (8)°
  • V = 5331.1 (15) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 113 (2) K
  • 0.26 × 0.24 × 0.10 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T min = 0.961, T max = 0.988
  • 32688 measured reflections
  • 6356 independent reflections
  • 5271 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.123
  • S = 1.09
  • 6356 reflections
  • 291 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2005).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002055/rk2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002055/rk2071Isup2.hkl

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

supplementary crystallographic information

Comment

Cyclopentenones are common structural units in bioactive natural products and useful building blocks. For a review see: (Roberts et al., 2002). While various approaches such as the Nazarov reaction (Frontier & Collison, 2005), Pauson–Khand reaction (Geis & Schmalz, 1998), Rautenstrauch rearrangement reaction (Shi et al., 2005), and intramolecular hydroacylation reaction (Tanaka & Fu, 2001) have been developed for construction of this important ring system. The title molecule was synthesized by [4 + 1] reaction of triisopropylsilyl vinyl ketene with Kobrich reagent (Li et al., 2007; Li et al., 2008).

The molecule structure of C27H44O4Si, is illustrated on Fig.1. The molecule consists of one cyclopentenone (C1–C5) and one phenyl ring (C6–C11). These rings are form the dihedral angle 73.2 (6)°. In the title molecule all bond lengths and bond angles are agree with published (Allen et al., 1987).

Experimental

A solution of the tricarbonyl chromium complexed silyl vinylketene (0.5 mmol) and CH2I2 or Br2CHCH3 (0.75 mmol) in 5 ml of Et2O was cooled to 195 K. The nBuLi (0.75 mmol) was added within 10 min by syringe. After stirring at 195 K for 1 h, the solution was allowed to warm to room temperature and stirred overnight. The resulting solution was diluted with 30 ml of Et2O and extracted with saturated NaCl (3 × 10 ml). The aqueous layer was backextracted with Et2O (3 × 10 ml). The combined organic layer was dried over anhydrous Na2SO4. After filtration, the solvent was removed under reduced pressure and the residue was purified via flash chromatography (SiO2) to afford the cyclopentenone compound (yield 78%, m.p. 332–333 K). 1H NMR (CDCl3): 6.46 (t, 1H), 6.36 (d, 2H), 3.79 (s, 6H), 3.24 (s, 3H), 2.66 (d, 1H), 2.42 (d, 1H), 1.68–1.63 (m, 1H), 1.44–1.39 (m, 1H), 1.35–1.12 (m, 7H), 0.98 (d, 9H), 0.94 (d, 9H), 0.84 (t, 3H) p.p.m.; 13C NMR (CDCl3): 210.0, 183.3, 159.8, 143.0, 137.5, 106.2, 100.2, 87.0, 55.3, 50.7, 42.2, 36.9, 26.5, 23.0, 19.2, 19.1, 14.0, 11.4 p.p.m..

Refinement

All H atoms were placed in calculated positions and refined as riding, with C—H = 0.95–1.00Å and with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecule structure of title compound with atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres with the arbitrary radius.

Crystal data

C27H44O4SiF000 = 2016
Mr = 460.71Dx = 1.148 Mg m3
Monoclinic, C2/cMelting point = 332–333 K
Hall symbol: -C 2ycMo Kα radiation λ = 0.71070 Å
a = 39.294 (4) ÅCell parameters from 374 reflections
b = 8.3327 (10) Åθ = 1.9–27.9º
c = 29.274 (3) ŵ = 0.12 mm1
β = 146.207 (8)ºT = 113 (2) K
V = 5331.1 (15) Å3Block, colourless
Z = 80.26 × 0.24 × 0.10 mm

Data collection

Rigaku Saturn diffractometer6356 independent reflections
Radiation source: rotating anode5271 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.051
Detector resolution: 7.31 pixels mm-1θmax = 27.9º
T = 113(2) Kθmin = 1.9º
ω scansh = −51→49
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −10→10
Tmin = 0.961, Tmax = 0.988l = −37→38
32688 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049  w = 1/[σ2(Fo2) + (0.0613P)2 + 2.2212P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123(Δ/σ)max = 0.001
S = 1.09Δρmax = 0.29 e Å3
6356 reflectionsΔρmin = −0.34 e Å3
291 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (3)
Secondary atom site location: difference Fourier map

Special details

Geometry. All s.u.'s (except the s.u.'s in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

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

xyzUiso*/Ueq
Si10.060076 (17)0.46916 (5)0.45150 (2)0.01708 (12)
O10.14533 (5)0.38982 (14)0.63443 (6)0.0260 (3)
O20.22955 (5)0.04752 (12)0.61756 (6)0.0191 (2)
O30.13563 (5)0.06140 (13)0.35883 (7)0.0249 (3)
O40.21072 (5)0.59302 (13)0.45866 (7)0.0257 (3)
C10.16047 (6)0.32410 (18)0.61599 (8)0.0185 (3)
C20.13558 (6)0.35913 (17)0.54188 (8)0.0162 (3)
C30.17437 (6)0.29104 (16)0.55487 (8)0.0148 (3)
C40.22794 (6)0.20168 (17)0.63719 (8)0.0166 (3)
C50.20858 (6)0.19464 (18)0.66571 (8)0.0198 (3)
H5A0.19140.08810.65420.024*
H5B0.24370.21700.72530.024*
C60.17257 (6)0.30081 (16)0.50223 (8)0.0153 (3)
C70.15364 (6)0.16823 (17)0.45500 (8)0.0171 (3)
H70.14110.07160.45550.021*
C80.15356 (6)0.18095 (17)0.40790 (8)0.0184 (3)
C90.17267 (6)0.32121 (18)0.40742 (8)0.0192 (3)
H90.17270.32800.37510.023*
C100.19146 (6)0.44980 (17)0.45446 (9)0.0179 (3)
C110.19134 (6)0.44033 (17)0.50188 (8)0.0179 (3)
H110.20420.52970.53390.021*
C120.11224 (8)−0.08178 (19)0.35246 (11)0.0313 (4)
H12A0.1013−0.15740.31590.038*
H12B0.0758−0.05660.33000.038*
H12C0.1435−0.13010.40700.038*
C130.21186 (7)0.6089 (2)0.41147 (10)0.0250 (3)
H13A0.22640.71640.41950.030*
H13B0.17050.59310.35320.030*
H13C0.23940.52820.42920.030*
C140.27015 (7)−0.06577 (18)0.68287 (9)0.0252 (3)
H14A0.2682−0.16680.66360.030*
H14B0.2582−0.08480.70140.030*
H14C0.3120−0.02370.72860.030*
C150.28884 (6)0.29106 (17)0.69819 (8)0.0180 (3)
H15A0.32190.22730.74940.022*
H15B0.29750.29680.67460.022*
C160.29095 (7)0.46110 (18)0.72010 (9)0.0214 (3)
H16A0.27670.45820.73640.026*
H16B0.26230.52970.67070.026*
C170.35466 (7)0.53686 (19)0.78964 (9)0.0233 (3)
H17A0.35340.64090.80460.028*
H17B0.38370.46620.83840.028*
C180.37830 (8)0.5645 (2)0.76797 (11)0.0303 (4)
H18A0.41930.61200.81510.036*
H18B0.35060.63740.72090.036*
H18C0.38030.46180.75390.036*
C190.07163 (7)0.69311 (19)0.47085 (10)0.0267 (3)
H190.03040.74380.42140.032*
C200.11217 (9)0.7634 (2)0.47859 (13)0.0409 (5)
H20A0.09670.73010.43130.049*
H20B0.15420.72440.52930.049*
H20C0.11170.88080.48010.049*
C210.09602 (12)0.7453 (2)0.54452 (14)0.0511 (6)
H21A0.07010.70040.53980.061*
H21B0.09560.86270.54600.061*
H21C0.13800.70640.59510.061*
C220.01096 (6)0.39689 (19)0.44564 (9)0.0225 (3)
H220.02940.44410.49440.027*
C230.01070 (8)0.2140 (2)0.45283 (11)0.0313 (4)
H23A0.05290.17480.50170.038*
H23B−0.01030.16170.40380.038*
H23C−0.01070.18900.45760.038*
C24−0.05484 (7)0.4611 (2)0.37011 (10)0.0308 (4)
H24A−0.05400.57770.36660.037*
H24B−0.07600.43590.37510.037*
H24C−0.07650.41070.32040.037*
C250.02599 (7)0.4266 (2)0.35538 (9)0.0249 (3)
H250.06000.43750.37070.030*
C260.00158 (8)0.2545 (2)0.32357 (10)0.0353 (4)
H26A0.03340.17840.36840.042*
H26B−0.00970.23410.27910.042*
H26C−0.03450.24130.30290.042*
C27−0.02368 (8)0.5469 (3)0.28563 (10)0.0382 (5)
H27A−0.00780.65640.30630.046*
H27B−0.05960.53390.26530.046*
H27C−0.03530.52710.24080.046*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Si10.01359 (19)0.0209 (2)0.01541 (19)0.00036 (15)0.01180 (17)0.00101 (15)
O10.0252 (6)0.0377 (7)0.0214 (5)0.0034 (5)0.0206 (5)0.0003 (5)
O20.0233 (5)0.0154 (5)0.0166 (5)0.0039 (4)0.0162 (5)0.0030 (4)
O30.0357 (6)0.0215 (6)0.0267 (6)−0.0029 (5)0.0277 (5)−0.0047 (4)
O40.0393 (6)0.0213 (6)0.0349 (6)−0.0050 (5)0.0342 (6)−0.0016 (5)
C10.0163 (6)0.0234 (7)0.0148 (6)−0.0019 (6)0.0127 (6)−0.0005 (5)
C20.0156 (6)0.0189 (7)0.0144 (6)−0.0024 (5)0.0125 (6)−0.0018 (5)
C30.0156 (6)0.0145 (7)0.0134 (6)−0.0025 (5)0.0119 (6)−0.0019 (5)
C40.0179 (7)0.0164 (7)0.0151 (6)0.0014 (5)0.0137 (6)0.0007 (5)
C50.0198 (7)0.0246 (8)0.0158 (7)0.0015 (6)0.0149 (6)0.0026 (6)
C60.0129 (6)0.0188 (7)0.0129 (6)0.0031 (5)0.0105 (6)0.0027 (5)
C70.0175 (6)0.0166 (7)0.0166 (6)0.0015 (5)0.0140 (6)0.0022 (5)
C80.0191 (7)0.0181 (7)0.0169 (6)0.0025 (5)0.0148 (6)0.0000 (5)
C90.0208 (7)0.0236 (8)0.0174 (7)0.0043 (6)0.0167 (6)0.0039 (6)
C100.0184 (7)0.0186 (7)0.0188 (7)0.0017 (5)0.0158 (6)0.0034 (5)
C110.0190 (7)0.0195 (7)0.0170 (7)−0.0011 (5)0.0153 (6)−0.0010 (5)
C120.0424 (10)0.0223 (8)0.0343 (9)−0.0074 (7)0.0328 (9)−0.0087 (7)
C130.0290 (8)0.0302 (9)0.0269 (8)−0.0033 (7)0.0253 (7)0.0012 (6)
C140.0263 (8)0.0210 (8)0.0208 (7)0.0051 (6)0.0182 (7)0.0056 (6)
C150.0157 (6)0.0201 (7)0.0152 (6)0.0019 (5)0.0123 (6)0.0005 (5)
C160.0206 (7)0.0216 (8)0.0209 (7)−0.0004 (6)0.0171 (7)−0.0030 (6)
C170.0223 (7)0.0230 (8)0.0200 (7)−0.0025 (6)0.0167 (7)−0.0038 (6)
C180.0303 (9)0.0297 (9)0.0350 (9)−0.0028 (7)0.0279 (8)−0.0012 (7)
C190.0281 (8)0.0224 (8)0.0327 (8)0.0022 (6)0.0258 (8)0.0034 (6)
C200.0494 (11)0.0273 (10)0.0606 (13)−0.0089 (8)0.0484 (11)−0.0047 (9)
C210.0878 (17)0.0259 (10)0.0725 (15)−0.0118 (10)0.0728 (15)−0.0132 (10)
C220.0166 (7)0.0304 (9)0.0206 (7)−0.0015 (6)0.0155 (6)−0.0009 (6)
C230.0285 (8)0.0318 (9)0.0371 (9)−0.0053 (7)0.0279 (8)−0.0001 (7)
C240.0193 (7)0.0450 (10)0.0288 (8)0.0033 (7)0.0201 (7)0.0044 (7)
C250.0162 (7)0.0404 (10)0.0163 (7)0.0005 (6)0.0131 (6)0.0019 (6)
C260.0277 (9)0.0515 (11)0.0261 (8)−0.0100 (8)0.0222 (8)−0.0146 (8)
C270.0228 (8)0.0643 (13)0.0210 (8)0.0104 (8)0.0170 (8)0.0124 (8)

Geometric parameters (Å, °)

Si1—C221.8886 (15)C15—H15A0.9900
Si1—C251.8902 (16)C15—H15B0.9900
Si1—C191.8926 (17)C16—C171.529 (2)
Si1—C21.8962 (15)C16—H16A0.9900
O1—C11.2161 (17)C16—H16B0.9900
O2—C141.4220 (17)C17—C181.516 (5)
O2—C41.4299 (17)C17—H17A0.9900
O3—C81.3674 (17)C17—H17B0.9900
O3—C121.4206 (19)C18—H18A0.9800
O4—C101.3630 (17)C18—H18B0.9800
O4—C131.425 (4)C18—H18C0.9800
C1—C21.4905 (19)C19—C211.525 (2)
C1—C51.511 (2)C19—C201.527 (6)
C2—C31.351 (4)C19—H191.0000
C3—C61.485 (4)C20—H20A0.9800
C3—C41.5366 (19)C20—H20B0.9800
C4—C51.528 (4)C20—H20C0.9800
C4—C151.5384 (19)C21—H21A0.9800
C5—H5A0.9900C21—H21B0.9800
C5—H5B0.9900C21—H21C0.9800
C6—C111.381 (2)C22—C241.536 (2)
C6—C71.4057 (19)C22—C231.540 (2)
C7—C81.380 (2)C22—H221.0000
C7—H70.9500C23—H23A0.9800
C8—C91.396 (2)C23—H23B0.9800
C9—C101.378 (2)C23—H23C0.9800
C9—H90.9500C24—H24A0.9800
C10—C111.394 (2)C24—H24B0.9800
C11—H110.9500C24—H24C0.9800
C12—H12A0.9800C25—C261.536 (2)
C12—H12B0.9800C25—C271.536 (2)
C12—H12C0.9800C25—H251.0000
C13—H13A0.9800C26—H26A0.9800
C13—H13B0.9800C26—H26B0.9800
C13—H13C0.9800C26—H26C0.9800
C14—H14A0.9800C27—H27A0.9800
C14—H14B0.9800C27—H27B0.9800
C14—H14C0.9800C27—H27C0.9800
C15—C161.529 (2)
C22—Si1—C25113.49 (7)C15—C16—C17113.52 (12)
C22—Si1—C19108.33 (7)C15—C16—H16A108.9
C25—Si1—C19109.11 (7)C17—C16—H16A108.9
C22—Si1—C2105.57 (6)C15—C16—H16B108.9
C25—Si1—C2109.74 (7)C17—C16—H16B108.9
C19—Si1—C2110.56 (7)H16A—C16—H16B107.7
C14—O2—C4115.53 (11)C18—C17—C16113.59 (13)
C8—O3—C12117.52 (12)C18—C17—H17A108.8
C10—O4—C13117.17 (12)C16—C17—H17A108.8
O1—C1—C2125.91 (13)C18—C17—H17B108.8
O1—C1—C5125.15 (13)C16—C17—H17B108.8
C2—C1—C5108.93 (12)H17A—C17—H17B107.7
C3—C2—C1106.60 (12)C17—C18—H18A109.5
C3—C2—Si1133.35 (11)C17—C18—H18B109.5
C1—C2—Si1119.92 (10)H18A—C18—H18B109.5
C2—C3—C6127.95 (12)C17—C18—H18C109.5
C2—C3—C4113.55 (12)H18A—C18—H18C109.5
C6—C3—C4118.40 (11)H18B—C18—H18C109.5
O2—C4—C5113.17 (11)C21—C19—C20109.20 (16)
O2—C4—C3105.40 (10)C21—C19—Si1114.66 (12)
C5—C4—C3102.71 (11)C20—C19—Si1112.57 (12)
O2—C4—C15110.85 (11)C21—C19—H19106.6
C5—C4—C15112.62 (11)C20—C19—H19106.6
C3—C4—C15111.59 (11)Si1—C19—H19106.6
C1—C5—C4103.81 (11)C19—C20—H20A109.5
C1—C5—H5A111.0C19—C20—H20B109.5
C4—C5—H5A111.0H20A—C20—H20B109.5
C1—C5—H5B111.0C19—C20—H20C109.5
C4—C5—H5B111.0H20A—C20—H20C109.5
H5A—C5—H5B109.0H20B—C20—H20C109.5
C11—C6—C7120.24 (13)C19—C21—H21A109.5
C11—C6—C3119.24 (12)C19—C21—H21B109.5
C7—C6—C3120.49 (12)H21A—C21—H21B109.5
C8—C7—C6118.83 (13)C19—C21—H21C109.5
C8—C7—H7120.6H21A—C21—H21C109.5
C6—C7—H7120.6H21B—C21—H21C109.5
O3—C8—C7124.39 (13)C24—C22—C23110.32 (13)
O3—C8—C9114.29 (12)C24—C22—Si1112.98 (11)
C7—C8—C9121.32 (13)C23—C22—Si1115.18 (11)
C10—C9—C8119.15 (13)C24—C22—H22105.9
C10—C9—H9120.4C23—C22—H22105.9
C8—C9—H9120.4Si1—C22—H22105.9
O4—C10—C9124.54 (13)C22—C23—H23A109.5
O4—C10—C11114.90 (13)C22—C23—H23B109.5
C9—C10—C11120.56 (13)H23A—C23—H23B109.5
C6—C11—C10119.91 (13)C22—C23—H23C109.5
C6—C11—H11120.0H23A—C23—H23C109.5
C10—C11—H11120.0H23B—C23—H23C109.5
O3—C12—H12A109.5C22—C24—H24A109.5
O3—C12—H12B109.5C22—C24—H24B109.5
H12A—C12—H12B109.5H24A—C24—H24B109.5
O3—C12—H12C109.5C22—C24—H24C109.5
H12A—C12—H12C109.5H24A—C24—H24C109.5
H12B—C12—H12C109.5H24B—C24—H24C109.5
O4—C13—H13A109.5C26—C25—C27109.87 (14)
O4—C13—H13B109.5C26—C25—Si1113.00 (11)
H13A—C13—H13B109.5C27—C25—Si1113.70 (12)
O4—C13—H13C109.5C26—C25—H25106.6
H13A—C13—H13C109.5C27—C25—H25106.6
H13B—C13—H13C109.5Si1—C25—H25106.6
O2—C14—H14A109.5C25—C26—H26A109.5
O2—C14—H14B109.5C25—C26—H26B109.5
H14A—C14—H14B109.5H26A—C26—H26B109.5
O2—C14—H14C109.5C25—C26—H26C109.5
H14A—C14—H14C109.5H26A—C26—H26C109.5
H14B—C14—H14C109.5H26B—C26—H26C109.5
C16—C15—C4115.18 (12)C25—C27—H27A109.5
C16—C15—H15A108.5C25—C27—H27B109.5
C4—C15—H15A108.5H27A—C27—H27B109.5
C16—C15—H15B108.5C25—C27—H27C109.5
C4—C15—H15B108.5H27A—C27—H27C109.5
H15A—C15—H15B107.5H27B—C27—H27C109.5
O1—C1—C2—C3165.05 (14)C6—C7—C8—O3−179.32 (13)
C5—C1—C2—C3−14.12 (16)C6—C7—C8—C91.0 (2)
O1—C1—C2—Si1−18.4 (2)O3—C8—C9—C10179.69 (12)
C5—C1—C2—Si1162.46 (10)C7—C8—C9—C10−0.6 (2)
C22—Si1—C2—C3139.93 (15)C13—O4—C10—C9−0.6 (2)
C25—Si1—C2—C317.28 (17)C13—O4—C10—C11179.85 (13)
C19—Si1—C2—C3−103.13 (15)C8—C9—C10—O4−179.59 (13)
C22—Si1—C2—C1−35.56 (13)C8—C9—C10—C11−0.1 (2)
C25—Si1—C2—C1−158.21 (11)C7—C6—C11—C100.1 (2)
C19—Si1—C2—C181.38 (12)C3—C6—C11—C10178.29 (13)
C1—C2—C3—C6−175.35 (13)O4—C10—C11—C6179.88 (12)
Si1—C2—C3—C68.7 (2)C9—C10—C11—C60.3 (2)
C1—C2—C3—C41.09 (16)O2—C4—C15—C16177.07 (11)
Si1—C2—C3—C4−174.83 (11)C5—C4—C15—C16−55.00 (16)
C14—O2—C4—C5−59.75 (15)C3—C4—C15—C1659.92 (15)
C14—O2—C4—C3−171.23 (11)C4—C15—C16—C17171.84 (12)
C14—O2—C4—C1567.88 (15)C15—C16—C17—C1864.92 (17)
C2—C3—C4—O2130.51 (12)C22—Si1—C19—C2153.07 (15)
C6—C3—C4—O2−52.67 (15)C25—Si1—C19—C21177.07 (14)
C2—C3—C4—C511.79 (15)C2—Si1—C19—C21−62.15 (15)
C6—C3—C4—C5−171.39 (12)C22—Si1—C19—C20178.71 (12)
C2—C3—C4—C15−109.09 (14)C25—Si1—C19—C20−57.29 (14)
C6—C3—C4—C1567.72 (15)C2—Si1—C19—C2063.48 (14)
O1—C1—C5—C4−158.20 (14)C25—Si1—C22—C24−54.04 (14)
C2—C1—C5—C420.98 (15)C19—Si1—C22—C2467.30 (13)
O2—C4—C5—C1−132.07 (12)C2—Si1—C22—C24−174.26 (11)
C3—C4—C5—C1−18.94 (14)C25—Si1—C22—C2373.98 (13)
C15—C4—C5—C1101.23 (13)C19—Si1—C22—C23−164.68 (12)
C2—C3—C6—C1175.56 (19)C2—Si1—C22—C23−46.23 (13)
C4—C3—C6—C11−100.74 (15)C22—Si1—C25—C26−46.17 (13)
C2—C3—C6—C7−106.22 (17)C19—Si1—C25—C26−167.07 (11)
C4—C3—C6—C777.48 (16)C2—Si1—C25—C2671.66 (12)
C11—C6—C7—C8−0.7 (2)C22—Si1—C25—C2779.96 (13)
C3—C6—C7—C8−178.91 (12)C19—Si1—C25—C27−40.94 (14)
C12—O3—C8—C73.8 (2)C2—Si1—C25—C27−162.22 (11)
C12—O3—C8—C9−176.46 (13)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2071).

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