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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2281.
Published online 2010 August 11. doi:  10.1107/S160053681003148X
PMCID: PMC3007959

[4-(Di-tert-butyl­fluoro­silan­yl)phenyl]methanol

Abstract

The asymmetric unit of the title compound, C15H25FOSi, contains two independent mol­ecules. Each of the Si atoms approximates the expected tetra­hedral geometry with Si—F bond lengths of 1.6128 (11) and 1.6068 (11) Å in the two independent mol­ecules. In the crystal, supra­molecular chains along a are found mediated by O—H(...)O hydrogen bonds.

Related literature

For synthetic background, see: Iovkova et al. (2009 [triangle]). For related structures, see: Iovkova et al. (2009 [triangle]); Bradtmöller et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2281-scheme1.jpg

Experimental

Crystal data

  • C15H25FOSi
  • M r = 268.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2281-efi1.jpg
  • a = 8.3213 (5) Å
  • b = 12.4011 (7) Å
  • c = 17.1036 (9) Å
  • α = 103.581 (5)°
  • β = 101.553 (5)°
  • γ = 107.487 (5)°
  • V = 1564.96 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.15 mm−1
  • T = 173 K
  • 0.26 × 0.14 × 0.12 mm

Data collection

  • Xcalibur2 CCD diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.928, T max = 1.000
  • 5698 measured reflections
  • 5698 independent reflections
  • 3074 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.070
  • S = 0.81
  • 5698 reflections
  • 337 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2006 [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/S160053681003148X/tk2698sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003148X/tk2698Isup2.hkl

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

supplementary crystallographic information

Comment

In the title compound, (I), the Si atoms show a distorted tetrahedral configuration, with bond angles ranging from 104.23 (7) ° (F2—Si2—C21) to 118.45 (9) ° (C31—Si2—C35). The Si—F bond lengths of 1.6128 (11) Å (Si1—F1) and 1.6068 (11) Å (Si2—F2) are comparable with that in tert-butylfluorodiphenylsilane, Si—F = 1.6004 (10) Å (Bradtmöller et al., 2006). In the crystal packing, molecules aggregate into supramolecular chains along a via O–H···O hydrogen bonding, Table 1 and Fig. 2.

Experimental

The title compound was prepared according to a literature procedure (Iovkova et al., 2009). The crude product was recrystallized from hexane to give colourless crystals.

Refinement

The C-bound H atoms were geometrically placed (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The O—H atoms were located in a difference Fourier map but for each OH-groups, this was disordered over two positions of equal weight (from isotropic refinement).

Figures

Fig. 1.
The molecular structure of the first independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 30% probability level. Only one orientation of the disordered H atom of the OH group (bound to C7) is shown and the remaining ...
Fig. 2.
The molecular structure of the second independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 30% probability level. Only one orientation of the disordered H atom of the OH group (bound to C27) is shown and the ...
Fig. 3.
Supramolecular chain in the crystal of (I). One dimensional polymer is formed in a direction via OH···O-bridges. Each of the displayed H atoms is present 50% of the time and other H atoms have been omitted.

Crystal data

C15H25FOSiF(000) = 584
Mr = 268.44Dx = 1.139 Mg m3
Triclinic, P1Melting point: 355 K
a = 8.3213 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.4011 (7) ÅCell parameters from 5698 reflections
c = 17.1036 (9) Åθ = 2.5–25.5°
α = 103.581 (5)°µ = 0.15 mm1
β = 101.553 (5)°T = 173 K
γ = 107.487 (5)°Block, colourless
V = 1564.96 (18) Å30.26 × 0.14 × 0.12 mm
Z = 4

Data collection

Xcalibur2 CCD diffractometer5698 independent reflections
Radiation source: Enhance (Mo) X-ray Source3074 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 16.0560 pixels mm-1θmax = 25.5°, θmin = 2.5°
489 frames via ω–rotation (Δω = 1°) and two times 40 s per frame (8 sets at different κ–angles) scansh = −10→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −15→14
Tmin = 0.928, Tmax = 1.000l = 0→20
5698 measured reflections

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) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 0.81w = 1/[σ2(Fo2) + (0.0317P)2] where P = (Fo2 + 2Fc2)/3
5698 reflections(Δ/σ)max = 0.001
337 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.24 e Å3

Special details

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.

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

xyzUiso*/UeqOcc. (<1)
Si10.21087 (9)0.53468 (5)0.86407 (4)0.02174 (17)
Si20.14914 (9)−0.00184 (5)0.27572 (4)0.02178 (17)
F10.20462 (15)0.44023 (10)0.91521 (7)0.0292 (3)
F20.05148 (16)−0.13240 (9)0.28033 (7)0.0329 (3)
O70.5783 (3)0.43277 (19)0.53749 (11)0.0423 (6)
O27−0.1288 (3)0.40525 (16)0.50475 (12)0.0451 (6)
H7A0.660 (6)0.441 (4)0.525 (3)0.026*0.50
H27A−0.074 (5)0.456 (3)0.492 (3)0.025*0.50
H7B0.519 (6)0.447 (4)0.510 (3)0.017*0.50
H27B−0.213 (6)0.408 (3)0.520 (2)0.015*0.50
C10.2944 (3)0.48053 (18)0.77482 (12)0.0195 (5)
C20.3008 (3)0.36675 (18)0.75402 (12)0.0233 (5)
H2A0.26340.31770.78550.028*
C30.3610 (3)0.32447 (18)0.68797 (13)0.0259 (6)
H3A0.36190.24750.67550.031*
C40.4204 (3)0.39537 (19)0.64003 (12)0.0215 (5)
C50.4156 (3)0.50816 (19)0.65974 (13)0.0296 (6)
H5A0.45510.55730.62860.035*
C60.3529 (3)0.54993 (18)0.72536 (13)0.0280 (6)
H6A0.34980.62630.73670.034*
C70.4856 (3)0.3454 (2)0.56882 (13)0.0325 (6)
H7D0.56210.30550.58820.039*
H7C0.38560.28620.52340.039*
C11−0.0251 (3)0.51978 (18)0.82264 (13)0.0239 (5)
C12−0.1355 (3)0.38556 (19)0.78331 (14)0.0375 (6)
H12A−0.25660.37450.76010.056*
H12B−0.12660.34720.82580.056*
H12C−0.09230.35130.73950.056*
C13−0.0466 (3)0.5789 (2)0.75359 (14)0.0400 (7)
H13A−0.16870.56640.73170.060*
H13B−0.00530.54440.70910.060*
H13C0.02070.66290.77690.060*
C14−0.0985 (3)0.5731 (2)0.89152 (14)0.0403 (7)
H14A−0.22190.55560.86810.060*
H14B−0.03730.65790.91330.060*
H14C−0.08230.53910.93610.060*
C150.3711 (3)0.68180 (18)0.94140 (13)0.0271 (6)
C160.5595 (3)0.6837 (2)0.94900 (14)0.0395 (6)
H16A0.64190.75390.99300.059*
H16B0.58500.68400.89670.059*
H16C0.56910.61420.96200.059*
C170.3552 (3)0.78949 (19)0.91528 (14)0.0437 (7)
H17A0.44390.86140.95510.066*
H17B0.24070.79230.91400.066*
H17C0.37100.78200.86040.066*
C180.3433 (3)0.6950 (2)1.02885 (13)0.0445 (7)
H18A0.42520.77031.06760.067*
H18B0.36200.63171.04790.067*
H18C0.22510.69141.02560.067*
C210.0847 (3)0.09866 (18)0.35247 (12)0.0212 (5)
C22−0.0082 (3)0.05502 (19)0.40438 (13)0.0285 (6)
H22−0.0377−0.02510.40020.034*
C23−0.0583 (3)0.1263 (2)0.46184 (13)0.0319 (6)
H23−0.11940.09350.49570.038*
C24−0.0194 (3)0.24503 (19)0.47002 (13)0.0251 (6)
C250.0705 (3)0.29039 (19)0.41831 (13)0.0320 (6)
H250.09650.37000.42180.038*
C260.1225 (3)0.21910 (18)0.36147 (12)0.0276 (6)
H260.18460.25250.32810.033*
C27−0.0724 (3)0.3224 (2)0.53407 (14)0.0399 (7)
H27C−0.16660.27210.54950.048*
H27D0.02720.36480.58430.048*
C310.0532 (3)−0.00873 (18)0.16479 (12)0.0264 (5)
C320.1582 (3)0.0998 (2)0.14295 (13)0.0487 (7)
H32A0.27720.10340.14970.073*
H32B0.15810.17130.17980.073*
H32C0.10460.09220.08580.073*
C33−0.1372 (3)−0.0130 (2)0.15359 (14)0.0466 (7)
H33A−0.2040−0.08030.16710.070*
H33B−0.1898−0.02030.09630.070*
H33C−0.13630.05890.19040.070*
C340.0475 (3)−0.1222 (2)0.10223 (13)0.0426 (7)
H34A−0.0180−0.19080.11490.064*
H34B0.1654−0.12000.10670.064*
H34C−0.0084−0.12680.04610.064*
C350.3920 (3)0.02815 (18)0.31370 (12)0.0226 (5)
C360.4563 (3)−0.0465 (2)0.25128 (14)0.0396 (7)
H36A0.3878−0.12950.23810.059*
H36B0.5781−0.03210.27580.059*
H36C0.4432−0.02470.20070.059*
C370.5025 (3)0.15982 (19)0.33339 (14)0.0395 (6)
H37A0.46360.20780.37250.059*
H37B0.48880.18060.28250.059*
H37C0.62430.17360.35750.059*
C380.4238 (3)−0.0041 (2)0.39535 (14)0.0447 (7)
H38A0.3555−0.08650.38420.067*
H38B0.38940.04450.43630.067*
H38C0.54660.00980.41660.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Si10.0253 (4)0.0237 (4)0.0206 (4)0.0121 (3)0.0116 (3)0.0066 (3)
Si20.0236 (4)0.0189 (4)0.0209 (4)0.0072 (3)0.0062 (3)0.0039 (3)
F10.0361 (9)0.0327 (7)0.0269 (7)0.0165 (7)0.0139 (7)0.0150 (6)
F20.0346 (9)0.0207 (7)0.0438 (8)0.0079 (7)0.0158 (7)0.0103 (6)
O70.0370 (15)0.0663 (13)0.0395 (13)0.0232 (11)0.0288 (11)0.0246 (10)
O270.0452 (14)0.0305 (12)0.0754 (15)0.0197 (11)0.0415 (12)0.0170 (10)
C10.0163 (13)0.0234 (13)0.0196 (12)0.0072 (11)0.0062 (11)0.0073 (10)
C20.0263 (15)0.0230 (13)0.0254 (13)0.0091 (12)0.0149 (12)0.0101 (11)
C30.0264 (15)0.0213 (13)0.0298 (14)0.0102 (12)0.0106 (12)0.0035 (11)
C40.0155 (14)0.0312 (14)0.0190 (12)0.0107 (11)0.0070 (11)0.0053 (11)
C50.0349 (16)0.0336 (15)0.0322 (14)0.0161 (13)0.0205 (13)0.0182 (12)
C60.0383 (17)0.0234 (13)0.0294 (14)0.0173 (13)0.0163 (13)0.0076 (11)
C70.0378 (17)0.0440 (16)0.0269 (14)0.0253 (14)0.0162 (13)0.0121 (12)
C110.0287 (15)0.0222 (13)0.0260 (13)0.0137 (12)0.0116 (12)0.0084 (11)
C120.0235 (16)0.0381 (16)0.0454 (16)0.0085 (13)0.0065 (13)0.0101 (13)
C130.0327 (17)0.0486 (17)0.0431 (16)0.0206 (14)0.0060 (14)0.0189 (14)
C140.0360 (18)0.0456 (16)0.0499 (17)0.0237 (14)0.0239 (15)0.0130 (13)
C150.0295 (15)0.0238 (13)0.0273 (14)0.0099 (12)0.0124 (12)0.0031 (11)
C160.0307 (17)0.0383 (15)0.0377 (15)0.0089 (13)0.0068 (13)−0.0017 (12)
C170.0462 (19)0.0288 (15)0.0499 (17)0.0106 (14)0.0173 (15)0.0025 (13)
C180.0477 (19)0.0450 (17)0.0286 (15)0.0115 (15)0.0133 (14)−0.0050 (12)
C210.0217 (14)0.0258 (14)0.0173 (12)0.0109 (11)0.0037 (11)0.0077 (10)
C220.0283 (15)0.0249 (13)0.0330 (14)0.0096 (12)0.0092 (13)0.0103 (12)
C230.0263 (16)0.0484 (17)0.0275 (14)0.0163 (13)0.0134 (13)0.0158 (13)
C240.0247 (15)0.0349 (15)0.0202 (13)0.0178 (12)0.0072 (12)0.0071 (11)
C250.0435 (17)0.0268 (14)0.0307 (14)0.0189 (13)0.0142 (13)0.0070 (12)
C260.0383 (17)0.0277 (15)0.0234 (13)0.0133 (13)0.0169 (13)0.0116 (11)
C270.0365 (18)0.0518 (17)0.0350 (16)0.0263 (15)0.0126 (14)0.0051 (13)
C310.0300 (15)0.0261 (14)0.0183 (12)0.0101 (12)0.0023 (11)0.0028 (10)
C320.067 (2)0.0525 (18)0.0264 (15)0.0215 (16)0.0095 (15)0.0157 (13)
C330.0416 (18)0.0554 (18)0.0326 (15)0.0267 (15)−0.0075 (14)−0.0004 (13)
C340.0434 (18)0.0502 (17)0.0240 (14)0.0211 (15)−0.0011 (13)−0.0029 (12)
C350.0231 (15)0.0227 (13)0.0200 (13)0.0063 (12)0.0067 (12)0.0055 (10)
C360.0311 (17)0.0461 (16)0.0456 (16)0.0189 (14)0.0148 (14)0.0123 (13)
C370.0265 (16)0.0366 (16)0.0409 (16)0.0061 (13)−0.0006 (13)0.0022 (12)
C380.0347 (18)0.0645 (19)0.0401 (16)0.0214 (15)0.0070 (14)0.0247 (14)

Geometric parameters (Å, °)

Si1—F11.6131 (11)C16—H16C0.9600
Si1—C11.8677 (19)C17—H17A0.9600
Si1—C151.885 (2)C17—H17B0.9600
Si1—C111.886 (2)C17—H17C0.9600
Si2—F21.6072 (11)C18—H18A0.9600
Si2—C211.865 (2)C18—H18B0.9600
Si2—C311.876 (2)C18—H18C0.9600
Si2—C351.885 (2)C21—C221.389 (2)
O7—C71.412 (3)C21—C261.394 (3)
O7—H7A0.74 (5)C22—C231.377 (3)
O7—H7B0.70 (4)C22—H220.9300
O27—C271.402 (3)C23—C241.376 (3)
O27—H27A0.76 (3)C23—H230.9300
O27—H27B0.80 (4)C24—C251.380 (3)
C1—C21.392 (3)C24—C271.506 (3)
C1—C61.396 (2)C25—C261.381 (3)
C2—C31.382 (2)C25—H250.9300
C2—H2A0.9300C26—H260.9300
C3—C41.389 (2)C27—H27C0.9700
C3—H3A0.9300C27—H27D0.9700
C4—C51.374 (3)C31—C341.536 (3)
C4—C71.508 (3)C31—C321.540 (3)
C5—C61.387 (3)C31—C331.540 (3)
C5—H5A0.9300C32—H32A0.9600
C6—H6A0.9300C32—H32B0.9600
C7—H7D0.9700C32—H32C0.9600
C7—H7C0.9700C33—H33A0.9600
C11—C141.538 (3)C33—H33B0.9600
C11—C131.538 (3)C33—H33C0.9600
C11—C121.541 (3)C34—H34A0.9600
C12—H12A0.9600C34—H34B0.9600
C12—H12B0.9600C34—H34C0.9600
C12—H12C0.9600C35—C371.530 (3)
C13—H13A0.9600C35—C361.531 (3)
C13—H13B0.9600C35—C381.535 (2)
C13—H13C0.9600C36—H36A0.9600
C14—H14A0.9600C36—H36B0.9600
C14—H14B0.9600C36—H36C0.9600
C14—H14C0.9600C37—H37A0.9600
C15—C171.537 (3)C37—H37B0.9600
C15—C181.538 (3)C37—H37C0.9600
C15—C161.540 (3)C38—H38A0.9600
C16—H16A0.9600C38—H38B0.9600
C16—H16B0.9600C38—H38C0.9600
F1—Si1—C1104.81 (8)C15—C17—H17C109.5
F1—Si1—C15104.91 (8)H17A—C17—H17C109.5
C1—Si1—C15112.43 (9)H17B—C17—H17C109.5
F1—Si1—C11105.55 (8)C15—C18—H18A109.5
C1—Si1—C11109.86 (9)C15—C18—H18B109.5
C15—Si1—C11118.05 (10)H18A—C18—H18B109.5
F2—Si2—C21104.23 (8)C15—C18—H18C109.5
F2—Si2—C31105.14 (8)H18A—C18—H18C109.5
C21—Si2—C31111.74 (9)H18B—C18—H18C109.5
F2—Si2—C35105.42 (8)C22—C21—C26115.72 (18)
C21—Si2—C35110.49 (10)C22—C21—Si2120.48 (15)
C31—Si2—C35118.46 (9)C26—C21—Si2123.79 (14)
C7—O7—H7A131 (3)C23—C22—C21122.27 (19)
C7—O7—H7B111 (4)C23—C22—H22118.9
H7A—O7—H7B109 (5)C21—C22—H22118.9
C27—O27—H27A127 (4)C24—C23—C22121.22 (18)
C27—O27—H27B108 (3)C24—C23—H23119.4
H27A—O27—H27B122 (5)C22—C23—H23119.4
C2—C1—C6116.25 (17)C23—C24—C25117.76 (19)
C2—C1—Si1120.95 (14)C23—C24—C27120.68 (18)
C6—C1—Si1122.80 (15)C25—C24—C27121.56 (19)
C3—C2—C1122.00 (17)C24—C25—C26120.90 (19)
C3—C2—H2A119.0C24—C25—H25119.5
C1—C2—H2A119.0C26—C25—H25119.5
C2—C3—C4120.86 (19)C25—C26—C21122.12 (18)
C2—C3—H3A119.6C25—C26—H26118.9
C4—C3—H3A119.6C21—C26—H26118.9
C5—C4—C3118.02 (17)O27—C27—C24112.91 (17)
C5—C4—C7123.09 (17)O27—C27—H27C109.0
C3—C4—C7118.89 (18)C24—C27—H27C109.0
C4—C5—C6121.05 (18)O27—C27—H27D109.0
C4—C5—H5A119.5C24—C27—H27D109.0
C6—C5—H5A119.5H27C—C27—H27D107.8
C5—C6—C1121.81 (19)C34—C31—C32108.43 (17)
C5—C6—H6A119.1C34—C31—C33108.07 (19)
C1—C6—H6A119.1C32—C31—C33108.64 (18)
O7—C7—C4113.41 (18)C34—C31—Si2110.55 (14)
O7—C7—H7D108.9C32—C31—Si2112.49 (15)
C4—C7—H7D108.9C33—C31—Si2108.54 (14)
O7—C7—H7C108.9C31—C32—H32A109.5
C4—C7—H7C108.9C31—C32—H32B109.5
H7D—C7—H7C107.7H32A—C32—H32B109.5
C14—C11—C13108.45 (17)C31—C32—H32C109.5
C14—C11—C12108.59 (17)H32A—C32—H32C109.5
C13—C11—C12108.09 (18)H32B—C32—H32C109.5
C14—C11—Si1113.09 (15)C31—C33—H33A109.5
C13—C11—Si1111.37 (14)C31—C33—H33B109.5
C12—C11—Si1107.10 (14)H33A—C33—H33B109.5
C11—C12—H12A109.5C31—C33—H33C109.5
C11—C12—H12B109.5H33A—C33—H33C109.5
H12A—C12—H12B109.5H33B—C33—H33C109.5
C11—C12—H12C109.5C31—C34—H34A109.5
H12A—C12—H12C109.5C31—C34—H34B109.5
H12B—C12—H12C109.5H34A—C34—H34B109.5
C11—C13—H13A109.5C31—C34—H34C109.5
C11—C13—H13B109.5H34A—C34—H34C109.5
H13A—C13—H13B109.5H34B—C34—H34C109.5
C11—C13—H13C109.5C37—C35—C36108.51 (16)
H13A—C13—H13C109.5C37—C35—C38108.29 (18)
H13B—C13—H13C109.5C36—C35—C38108.12 (17)
C11—C14—H14A109.5C37—C35—Si2111.45 (15)
C11—C14—H14B109.5C36—C35—Si2113.31 (15)
H14A—C14—H14B109.5C38—C35—Si2106.99 (13)
C11—C14—H14C109.5C35—C36—H36A109.5
H14A—C14—H14C109.5C35—C36—H36B109.5
H14B—C14—H14C109.5H36A—C36—H36B109.5
C17—C15—C18108.54 (17)C35—C36—H36C109.5
C17—C15—C16108.67 (18)H36A—C36—H36C109.5
C18—C15—C16107.65 (19)H36B—C36—H36C109.5
C17—C15—Si1113.11 (16)C35—C37—H37A109.5
C18—C15—Si1110.18 (14)C35—C37—H37B109.5
C16—C15—Si1108.54 (15)H37A—C37—H37B109.5
C15—C16—H16A109.5C35—C37—H37C109.5
C15—C16—H16B109.5H37A—C37—H37C109.5
H16A—C16—H16B109.5H37B—C37—H37C109.5
C15—C16—H16C109.5C35—C38—H38A109.5
H16A—C16—H16C109.5C35—C38—H38B109.5
H16B—C16—H16C109.5H38A—C38—H38B109.5
C15—C17—H17A109.5C35—C38—H38C109.5
C15—C17—H17B109.5H38A—C38—H38C109.5
H17A—C17—H17B109.5H38B—C38—H38C109.5
F1—Si1—C1—C213.58 (19)F2—Si2—C21—C227.40 (19)
C15—Si1—C1—C2126.97 (18)C31—Si2—C21—C22120.43 (18)
C11—Si1—C1—C2−99.40 (18)C35—Si2—C21—C22−105.41 (18)
F1—Si1—C1—C6−166.59 (17)F2—Si2—C21—C26−171.79 (17)
C15—Si1—C1—C6−53.2 (2)C31—Si2—C21—C26−58.8 (2)
C11—Si1—C1—C680.4 (2)C35—Si2—C21—C2675.4 (2)
C6—C1—C2—C3−0.2 (3)C26—C21—C22—C23−0.7 (3)
Si1—C1—C2—C3179.61 (17)Si2—C21—C22—C23−179.99 (17)
C1—C2—C3—C40.9 (3)C21—C22—C23—C240.6 (3)
C2—C3—C4—C5−0.6 (3)C22—C23—C24—C250.4 (3)
C2—C3—C4—C7179.7 (2)C22—C23—C24—C27−179.0 (2)
C3—C4—C5—C6−0.2 (3)C23—C24—C25—C26−1.2 (3)
C7—C4—C5—C6179.4 (2)C27—C24—C25—C26178.2 (2)
C4—C5—C6—C10.9 (3)C24—C25—C26—C211.1 (3)
C2—C1—C6—C5−0.6 (3)C22—C21—C26—C25−0.1 (3)
Si1—C1—C6—C5179.53 (17)Si2—C21—C26—C25179.14 (18)
C5—C4—C7—O714.0 (3)C23—C24—C27—O27−141.9 (2)
C3—C4—C7—O7−166.4 (2)C25—C24—C27—O2738.8 (3)
F1—Si1—C11—C1472.77 (15)F2—Si2—C31—C34−46.43 (16)
C1—Si1—C11—C14−174.73 (14)C21—Si2—C31—C34−158.90 (15)
C15—Si1—C11—C14−44.03 (17)C35—Si2—C31—C3470.95 (17)
F1—Si1—C11—C13−164.80 (14)F2—Si2—C31—C32−167.81 (14)
C1—Si1—C11—C13−52.30 (17)C21—Si2—C31—C3279.72 (17)
C15—Si1—C11—C1378.40 (16)C35—Si2—C31—C32−50.43 (18)
F1—Si1—C11—C12−46.82 (14)F2—Si2—C31—C3371.93 (16)
C1—Si1—C11—C1265.68 (14)C21—Si2—C31—C33−40.53 (17)
C15—Si1—C11—C12−163.61 (12)C35—Si2—C31—C33−170.68 (14)
F1—Si1—C15—C17−162.48 (14)F2—Si2—C35—C37−166.07 (12)
C1—Si1—C15—C1784.19 (17)C21—Si2—C35—C37−54.03 (15)
C11—Si1—C15—C17−45.33 (17)C31—Si2—C35—C3776.69 (16)
F1—Si1—C15—C18−40.80 (17)F2—Si2—C35—C3671.20 (14)
C1—Si1—C15—C18−154.13 (14)C21—Si2—C35—C36−176.76 (13)
C11—Si1—C15—C1876.35 (17)C31—Si2—C35—C36−46.05 (17)
F1—Si1—C15—C1676.84 (14)F2—Si2—C35—C38−47.87 (15)
C1—Si1—C15—C16−36.49 (17)C21—Si2—C35—C3864.17 (15)
C11—Si1—C15—C16−166.01 (13)C31—Si2—C35—C38−165.11 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7A···O27i0.74 (5)2.01 (5)2.707 (3)157 (5)
O27—H27A···O27ii0.76 (3)2.00 (3)2.727 (3)160 (5)
O7—H7B···O7iii0.70 (4)2.14 (3)2.787 (4)154 (5)
O27—H27B···O7iv0.80 (4)1.92 (5)2.707 (3)167 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2698).

References

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  • Brandenburg, K. (2006). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Iovkova, L., Wängler, B., Schirrmacher, E., Schirrmacher, R., Quandt, G., Boening, G., Schürmann, M. & Jurkschat, K. (2009). Chem. Eur. J.15, 2140–2147. [PubMed]
  • Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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