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organic compounds
[4-(Di-tert-butylfluorosilanyl)phenyl]methanol
aFakultät Chemie, Technische Universität Dortmund, 44221 Dortmund, Germany
*Correspondence e-mail: klaus.jurkschat@tu-dortmund.de
The 15H25FOSi, 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.
of the title compound, CRelated literature
For synthetic background, see: Iovkova et al. (2009). For related structures, see: Iovkova et al. (2009
); Bradtmöller et al. (2006
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell CrysAlis RED (Oxford Diffraction, 2008
); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: DIAMOND (Brandenburg, 2006
); software used to prepare material for publication: publCIF (Westrip, 2010
).
Supporting information
https://doi.org/10.1107/S160053681003148X/tk2698sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003148X/tk2698Isup2.hkl
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.
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).
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.
For synthetic background and in the context of application [of the title compound?] in positron emission tomography (PET), see: Iovkova et al. (2009). For related structures, see: Iovkova et al. (2009); Bradtmöller et al. (2006).
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell
CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C15H25FOSi | F(000) = 584 |
Mr = 268.44 | Dx = 1.139 Mg m−3 |
Triclinic, P1 | Melting point: 355 K |
a = 8.3213 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.4011 (7) Å | Cell parameters from 5698 reflections |
c = 17.1036 (9) Å | θ = 2.5–25.5° |
α = 103.581 (5)° | µ = 0.15 mm−1 |
β = 101.553 (5)° | T = 173 K |
γ = 107.487 (5)° | Block, colourless |
V = 1564.96 (18) Å3 | 0.26 × 0.14 × 0.12 mm |
Z = 4 |
Xcalibur2 CCD diffractometer | 5698 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3074 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 16.0560 pixels mm-1 | θmax = 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) scans | h = −10→9 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008) | k = −15→14 |
Tmin = 0.928, Tmax = 1.000 | l = 0→20 |
5698 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | w = 1/[σ2(Fo2) + (0.0317P)2] where P = (Fo2 + 2Fc2)/3 |
5698 reflections | (Δ/σ)max = 0.001 |
337 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C15H25FOSi | γ = 107.487 (5)° |
Mr = 268.44 | V = 1564.96 (18) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.3213 (5) Å | Mo Kα radiation |
b = 12.4011 (7) Å | µ = 0.15 mm−1 |
c = 17.1036 (9) Å | T = 173 K |
α = 103.581 (5)° | 0.26 × 0.14 × 0.12 mm |
β = 101.553 (5)° |
Xcalibur2 CCD diffractometer | 5698 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008) | 3074 reflections with I > 2σ(I) |
Tmin = 0.928, Tmax = 1.000 | Rint = 0.042 |
5698 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.27 e Å−3 |
5698 reflections | Δρmin = −0.24 e Å−3 |
337 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Si1 | 0.21087 (9) | 0.53468 (5) | 0.86407 (4) | 0.02174 (17) | |
Si2 | 0.14914 (9) | −0.00184 (5) | 0.27572 (4) | 0.02178 (17) | |
F1 | 0.20462 (15) | 0.44023 (10) | 0.91521 (7) | 0.0292 (3) | |
F2 | 0.05148 (16) | −0.13240 (9) | 0.28033 (7) | 0.0329 (3) | |
O7 | 0.5783 (3) | 0.43277 (19) | 0.53749 (11) | 0.0423 (6) | |
O27 | −0.1288 (3) | 0.40525 (16) | 0.50475 (12) | 0.0451 (6) | |
H7A | 0.660 (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 |
H7B | 0.519 (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 |
C1 | 0.2944 (3) | 0.48053 (18) | 0.77482 (12) | 0.0195 (5) | |
C2 | 0.3008 (3) | 0.36675 (18) | 0.75402 (12) | 0.0233 (5) | |
H2A | 0.2634 | 0.3177 | 0.7855 | 0.028* | |
C3 | 0.3610 (3) | 0.32447 (18) | 0.68797 (13) | 0.0259 (6) | |
H3A | 0.3619 | 0.2475 | 0.6755 | 0.031* | |
C4 | 0.4204 (3) | 0.39537 (19) | 0.64003 (12) | 0.0215 (5) | |
C5 | 0.4156 (3) | 0.50816 (19) | 0.65974 (13) | 0.0296 (6) | |
H5A | 0.4551 | 0.5573 | 0.6286 | 0.035* | |
C6 | 0.3529 (3) | 0.54993 (18) | 0.72536 (13) | 0.0280 (6) | |
H6A | 0.3498 | 0.6263 | 0.7367 | 0.034* | |
C7 | 0.4856 (3) | 0.3454 (2) | 0.56882 (13) | 0.0325 (6) | |
H7D | 0.5621 | 0.3055 | 0.5882 | 0.039* | |
H7C | 0.3856 | 0.2862 | 0.5234 | 0.039* | |
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 | −0.2566 | 0.3745 | 0.7601 | 0.056* | |
H12B | −0.1266 | 0.3472 | 0.8258 | 0.056* | |
H12C | −0.0923 | 0.3513 | 0.7395 | 0.056* | |
C13 | −0.0466 (3) | 0.5789 (2) | 0.75359 (14) | 0.0400 (7) | |
H13A | −0.1687 | 0.5664 | 0.7317 | 0.060* | |
H13B | −0.0053 | 0.5444 | 0.7091 | 0.060* | |
H13C | 0.0207 | 0.6629 | 0.7769 | 0.060* | |
C14 | −0.0985 (3) | 0.5731 (2) | 0.89152 (14) | 0.0403 (7) | |
H14A | −0.2219 | 0.5556 | 0.8681 | 0.060* | |
H14B | −0.0373 | 0.6579 | 0.9133 | 0.060* | |
H14C | −0.0823 | 0.5391 | 0.9361 | 0.060* | |
C15 | 0.3711 (3) | 0.68180 (18) | 0.94140 (13) | 0.0271 (6) | |
C16 | 0.5595 (3) | 0.6837 (2) | 0.94900 (14) | 0.0395 (6) | |
H16A | 0.6419 | 0.7539 | 0.9930 | 0.059* | |
H16B | 0.5850 | 0.6840 | 0.8967 | 0.059* | |
H16C | 0.5691 | 0.6142 | 0.9620 | 0.059* | |
C17 | 0.3552 (3) | 0.78949 (19) | 0.91528 (14) | 0.0437 (7) | |
H17A | 0.4439 | 0.8614 | 0.9551 | 0.066* | |
H17B | 0.2407 | 0.7923 | 0.9140 | 0.066* | |
H17C | 0.3710 | 0.7820 | 0.8604 | 0.066* | |
C18 | 0.3433 (3) | 0.6950 (2) | 1.02885 (13) | 0.0445 (7) | |
H18A | 0.4252 | 0.7703 | 1.0676 | 0.067* | |
H18B | 0.3620 | 0.6317 | 1.0479 | 0.067* | |
H18C | 0.2251 | 0.6914 | 1.0256 | 0.067* | |
C21 | 0.0847 (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 | −0.0251 | 0.4002 | 0.034* | |
C23 | −0.0583 (3) | 0.1263 (2) | 0.46184 (13) | 0.0319 (6) | |
H23 | −0.1194 | 0.0935 | 0.4957 | 0.038* | |
C24 | −0.0194 (3) | 0.24503 (19) | 0.47002 (13) | 0.0251 (6) | |
C25 | 0.0705 (3) | 0.29039 (19) | 0.41831 (13) | 0.0320 (6) | |
H25 | 0.0965 | 0.3700 | 0.4218 | 0.038* | |
C26 | 0.1225 (3) | 0.21910 (18) | 0.36147 (12) | 0.0276 (6) | |
H26 | 0.1846 | 0.2525 | 0.3281 | 0.033* | |
C27 | −0.0724 (3) | 0.3224 (2) | 0.53407 (14) | 0.0399 (7) | |
H27C | −0.1666 | 0.2721 | 0.5495 | 0.048* | |
H27D | 0.0272 | 0.3648 | 0.5843 | 0.048* | |
C31 | 0.0532 (3) | −0.00873 (18) | 0.16479 (12) | 0.0264 (5) | |
C32 | 0.1582 (3) | 0.0998 (2) | 0.14295 (13) | 0.0487 (7) | |
H32A | 0.2772 | 0.1034 | 0.1497 | 0.073* | |
H32B | 0.1581 | 0.1713 | 0.1798 | 0.073* | |
H32C | 0.1046 | 0.0922 | 0.0858 | 0.073* | |
C33 | −0.1372 (3) | −0.0130 (2) | 0.15359 (14) | 0.0466 (7) | |
H33A | −0.2040 | −0.0803 | 0.1671 | 0.070* | |
H33B | −0.1898 | −0.0203 | 0.0963 | 0.070* | |
H33C | −0.1363 | 0.0589 | 0.1904 | 0.070* | |
C34 | 0.0475 (3) | −0.1222 (2) | 0.10223 (13) | 0.0426 (7) | |
H34A | −0.0180 | −0.1908 | 0.1149 | 0.064* | |
H34B | 0.1654 | −0.1200 | 0.1067 | 0.064* | |
H34C | −0.0084 | −0.1268 | 0.0461 | 0.064* | |
C35 | 0.3920 (3) | 0.02815 (18) | 0.31370 (12) | 0.0226 (5) | |
C36 | 0.4563 (3) | −0.0465 (2) | 0.25128 (14) | 0.0396 (7) | |
H36A | 0.3878 | −0.1295 | 0.2381 | 0.059* | |
H36B | 0.5781 | −0.0321 | 0.2758 | 0.059* | |
H36C | 0.4432 | −0.0247 | 0.2007 | 0.059* | |
C37 | 0.5025 (3) | 0.15982 (19) | 0.33339 (14) | 0.0395 (6) | |
H37A | 0.4636 | 0.2078 | 0.3725 | 0.059* | |
H37B | 0.4888 | 0.1806 | 0.2825 | 0.059* | |
H37C | 0.6243 | 0.1736 | 0.3575 | 0.059* | |
C38 | 0.4238 (3) | −0.0041 (2) | 0.39535 (14) | 0.0447 (7) | |
H38A | 0.3555 | −0.0865 | 0.3842 | 0.067* | |
H38B | 0.3894 | 0.0445 | 0.4363 | 0.067* | |
H38C | 0.5466 | 0.0098 | 0.4166 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.0253 (4) | 0.0237 (4) | 0.0206 (4) | 0.0121 (3) | 0.0116 (3) | 0.0066 (3) |
Si2 | 0.0236 (4) | 0.0189 (4) | 0.0209 (4) | 0.0072 (3) | 0.0062 (3) | 0.0039 (3) |
F1 | 0.0361 (9) | 0.0327 (7) | 0.0269 (7) | 0.0165 (7) | 0.0139 (7) | 0.0150 (6) |
F2 | 0.0346 (9) | 0.0207 (7) | 0.0438 (8) | 0.0079 (7) | 0.0158 (7) | 0.0103 (6) |
O7 | 0.0370 (15) | 0.0663 (13) | 0.0395 (13) | 0.0232 (11) | 0.0288 (11) | 0.0246 (10) |
O27 | 0.0452 (14) | 0.0305 (12) | 0.0754 (15) | 0.0197 (11) | 0.0415 (12) | 0.0170 (10) |
C1 | 0.0163 (13) | 0.0234 (13) | 0.0196 (12) | 0.0072 (11) | 0.0062 (11) | 0.0073 (10) |
C2 | 0.0263 (15) | 0.0230 (13) | 0.0254 (13) | 0.0091 (12) | 0.0149 (12) | 0.0101 (11) |
C3 | 0.0264 (15) | 0.0213 (13) | 0.0298 (14) | 0.0102 (12) | 0.0106 (12) | 0.0035 (11) |
C4 | 0.0155 (14) | 0.0312 (14) | 0.0190 (12) | 0.0107 (11) | 0.0070 (11) | 0.0053 (11) |
C5 | 0.0349 (16) | 0.0336 (15) | 0.0322 (14) | 0.0161 (13) | 0.0205 (13) | 0.0182 (12) |
C6 | 0.0383 (17) | 0.0234 (13) | 0.0294 (14) | 0.0173 (13) | 0.0163 (13) | 0.0076 (11) |
C7 | 0.0378 (17) | 0.0440 (16) | 0.0269 (14) | 0.0253 (14) | 0.0162 (13) | 0.0121 (12) |
C11 | 0.0287 (15) | 0.0222 (13) | 0.0260 (13) | 0.0137 (12) | 0.0116 (12) | 0.0084 (11) |
C12 | 0.0235 (16) | 0.0381 (16) | 0.0454 (16) | 0.0085 (13) | 0.0065 (13) | 0.0101 (13) |
C13 | 0.0327 (17) | 0.0486 (17) | 0.0431 (16) | 0.0206 (14) | 0.0060 (14) | 0.0189 (14) |
C14 | 0.0360 (18) | 0.0456 (16) | 0.0499 (17) | 0.0237 (14) | 0.0239 (15) | 0.0130 (13) |
C15 | 0.0295 (15) | 0.0238 (13) | 0.0273 (14) | 0.0099 (12) | 0.0124 (12) | 0.0031 (11) |
C16 | 0.0307 (17) | 0.0383 (15) | 0.0377 (15) | 0.0089 (13) | 0.0068 (13) | −0.0017 (12) |
C17 | 0.0462 (19) | 0.0288 (15) | 0.0499 (17) | 0.0106 (14) | 0.0173 (15) | 0.0025 (13) |
C18 | 0.0477 (19) | 0.0450 (17) | 0.0286 (15) | 0.0115 (15) | 0.0133 (14) | −0.0050 (12) |
C21 | 0.0217 (14) | 0.0258 (14) | 0.0173 (12) | 0.0109 (11) | 0.0037 (11) | 0.0077 (10) |
C22 | 0.0283 (15) | 0.0249 (13) | 0.0330 (14) | 0.0096 (12) | 0.0092 (13) | 0.0103 (12) |
C23 | 0.0263 (16) | 0.0484 (17) | 0.0275 (14) | 0.0163 (13) | 0.0134 (13) | 0.0158 (13) |
C24 | 0.0247 (15) | 0.0349 (15) | 0.0202 (13) | 0.0178 (12) | 0.0072 (12) | 0.0071 (11) |
C25 | 0.0435 (17) | 0.0268 (14) | 0.0307 (14) | 0.0189 (13) | 0.0142 (13) | 0.0070 (12) |
C26 | 0.0383 (17) | 0.0277 (15) | 0.0234 (13) | 0.0133 (13) | 0.0169 (13) | 0.0116 (11) |
C27 | 0.0365 (18) | 0.0518 (17) | 0.0350 (16) | 0.0263 (15) | 0.0126 (14) | 0.0051 (13) |
C31 | 0.0300 (15) | 0.0261 (14) | 0.0183 (12) | 0.0101 (12) | 0.0023 (11) | 0.0028 (10) |
C32 | 0.067 (2) | 0.0525 (18) | 0.0264 (15) | 0.0215 (16) | 0.0095 (15) | 0.0157 (13) |
C33 | 0.0416 (18) | 0.0554 (18) | 0.0326 (15) | 0.0267 (15) | −0.0075 (14) | −0.0004 (13) |
C34 | 0.0434 (18) | 0.0502 (17) | 0.0240 (14) | 0.0211 (15) | −0.0011 (13) | −0.0029 (12) |
C35 | 0.0231 (15) | 0.0227 (13) | 0.0200 (13) | 0.0063 (12) | 0.0067 (12) | 0.0055 (10) |
C36 | 0.0311 (17) | 0.0461 (16) | 0.0456 (16) | 0.0189 (14) | 0.0148 (14) | 0.0123 (13) |
C37 | 0.0265 (16) | 0.0366 (16) | 0.0409 (16) | 0.0061 (13) | −0.0006 (13) | 0.0022 (12) |
C38 | 0.0347 (18) | 0.0645 (19) | 0.0401 (16) | 0.0214 (15) | 0.0070 (14) | 0.0247 (14) |
Si1—F1 | 1.6131 (11) | C16—H16C | 0.9600 |
Si1—C1 | 1.8677 (19) | C17—H17A | 0.9600 |
Si1—C15 | 1.885 (2) | C17—H17B | 0.9600 |
Si1—C11 | 1.886 (2) | C17—H17C | 0.9600 |
Si2—F2 | 1.6072 (11) | C18—H18A | 0.9600 |
Si2—C21 | 1.865 (2) | C18—H18B | 0.9600 |
Si2—C31 | 1.876 (2) | C18—H18C | 0.9600 |
Si2—C35 | 1.885 (2) | C21—C22 | 1.389 (2) |
O7—C7 | 1.412 (3) | C21—C26 | 1.394 (3) |
O7—H7A | 0.74 (5) | C22—C23 | 1.377 (3) |
O7—H7B | 0.70 (4) | C22—H22 | 0.9300 |
O27—C27 | 1.402 (3) | C23—C24 | 1.376 (3) |
O27—H27A | 0.76 (3) | C23—H23 | 0.9300 |
O27—H27B | 0.80 (4) | C24—C25 | 1.380 (3) |
C1—C2 | 1.392 (3) | C24—C27 | 1.506 (3) |
C1—C6 | 1.396 (2) | C25—C26 | 1.381 (3) |
C2—C3 | 1.382 (2) | C25—H25 | 0.9300 |
C2—H2A | 0.9300 | C26—H26 | 0.9300 |
C3—C4 | 1.389 (2) | C27—H27C | 0.9700 |
C3—H3A | 0.9300 | C27—H27D | 0.9700 |
C4—C5 | 1.374 (3) | C31—C34 | 1.536 (3) |
C4—C7 | 1.508 (3) | C31—C32 | 1.540 (3) |
C5—C6 | 1.387 (3) | C31—C33 | 1.540 (3) |
C5—H5A | 0.9300 | C32—H32A | 0.9600 |
C6—H6A | 0.9300 | C32—H32B | 0.9600 |
C7—H7D | 0.9700 | C32—H32C | 0.9600 |
C7—H7C | 0.9700 | C33—H33A | 0.9600 |
C11—C14 | 1.538 (3) | C33—H33B | 0.9600 |
C11—C13 | 1.538 (3) | C33—H33C | 0.9600 |
C11—C12 | 1.541 (3) | C34—H34A | 0.9600 |
C12—H12A | 0.9600 | C34—H34B | 0.9600 |
C12—H12B | 0.9600 | C34—H34C | 0.9600 |
C12—H12C | 0.9600 | C35—C37 | 1.530 (3) |
C13—H13A | 0.9600 | C35—C36 | 1.531 (3) |
C13—H13B | 0.9600 | C35—C38 | 1.535 (2) |
C13—H13C | 0.9600 | C36—H36A | 0.9600 |
C14—H14A | 0.9600 | C36—H36B | 0.9600 |
C14—H14B | 0.9600 | C36—H36C | 0.9600 |
C14—H14C | 0.9600 | C37—H37A | 0.9600 |
C15—C17 | 1.537 (3) | C37—H37B | 0.9600 |
C15—C18 | 1.538 (3) | C37—H37C | 0.9600 |
C15—C16 | 1.540 (3) | C38—H38A | 0.9600 |
C16—H16A | 0.9600 | C38—H38B | 0.9600 |
C16—H16B | 0.9600 | C38—H38C | 0.9600 |
F1—Si1—C1 | 104.81 (8) | C15—C17—H17C | 109.5 |
F1—Si1—C15 | 104.91 (8) | H17A—C17—H17C | 109.5 |
C1—Si1—C15 | 112.43 (9) | H17B—C17—H17C | 109.5 |
F1—Si1—C11 | 105.55 (8) | C15—C18—H18A | 109.5 |
C1—Si1—C11 | 109.86 (9) | C15—C18—H18B | 109.5 |
C15—Si1—C11 | 118.05 (10) | H18A—C18—H18B | 109.5 |
F2—Si2—C21 | 104.23 (8) | C15—C18—H18C | 109.5 |
F2—Si2—C31 | 105.14 (8) | H18A—C18—H18C | 109.5 |
C21—Si2—C31 | 111.74 (9) | H18B—C18—H18C | 109.5 |
F2—Si2—C35 | 105.42 (8) | C22—C21—C26 | 115.72 (18) |
C21—Si2—C35 | 110.49 (10) | C22—C21—Si2 | 120.48 (15) |
C31—Si2—C35 | 118.46 (9) | C26—C21—Si2 | 123.79 (14) |
C7—O7—H7A | 131 (3) | C23—C22—C21 | 122.27 (19) |
C7—O7—H7B | 111 (4) | C23—C22—H22 | 118.9 |
H7A—O7—H7B | 109 (5) | C21—C22—H22 | 118.9 |
C27—O27—H27A | 127 (4) | C24—C23—C22 | 121.22 (18) |
C27—O27—H27B | 108 (3) | C24—C23—H23 | 119.4 |
H27A—O27—H27B | 122 (5) | C22—C23—H23 | 119.4 |
C2—C1—C6 | 116.25 (17) | C23—C24—C25 | 117.76 (19) |
C2—C1—Si1 | 120.95 (14) | C23—C24—C27 | 120.68 (18) |
C6—C1—Si1 | 122.80 (15) | C25—C24—C27 | 121.56 (19) |
C3—C2—C1 | 122.00 (17) | C24—C25—C26 | 120.90 (19) |
C3—C2—H2A | 119.0 | C24—C25—H25 | 119.5 |
C1—C2—H2A | 119.0 | C26—C25—H25 | 119.5 |
C2—C3—C4 | 120.86 (19) | C25—C26—C21 | 122.12 (18) |
C2—C3—H3A | 119.6 | C25—C26—H26 | 118.9 |
C4—C3—H3A | 119.6 | C21—C26—H26 | 118.9 |
C5—C4—C3 | 118.02 (17) | O27—C27—C24 | 112.91 (17) |
C5—C4—C7 | 123.09 (17) | O27—C27—H27C | 109.0 |
C3—C4—C7 | 118.89 (18) | C24—C27—H27C | 109.0 |
C4—C5—C6 | 121.05 (18) | O27—C27—H27D | 109.0 |
C4—C5—H5A | 119.5 | C24—C27—H27D | 109.0 |
C6—C5—H5A | 119.5 | H27C—C27—H27D | 107.8 |
C5—C6—C1 | 121.81 (19) | C34—C31—C32 | 108.43 (17) |
C5—C6—H6A | 119.1 | C34—C31—C33 | 108.07 (19) |
C1—C6—H6A | 119.1 | C32—C31—C33 | 108.64 (18) |
O7—C7—C4 | 113.41 (18) | C34—C31—Si2 | 110.55 (14) |
O7—C7—H7D | 108.9 | C32—C31—Si2 | 112.49 (15) |
C4—C7—H7D | 108.9 | C33—C31—Si2 | 108.54 (14) |
O7—C7—H7C | 108.9 | C31—C32—H32A | 109.5 |
C4—C7—H7C | 108.9 | C31—C32—H32B | 109.5 |
H7D—C7—H7C | 107.7 | H32A—C32—H32B | 109.5 |
C14—C11—C13 | 108.45 (17) | C31—C32—H32C | 109.5 |
C14—C11—C12 | 108.59 (17) | H32A—C32—H32C | 109.5 |
C13—C11—C12 | 108.09 (18) | H32B—C32—H32C | 109.5 |
C14—C11—Si1 | 113.09 (15) | C31—C33—H33A | 109.5 |
C13—C11—Si1 | 111.37 (14) | C31—C33—H33B | 109.5 |
C12—C11—Si1 | 107.10 (14) | H33A—C33—H33B | 109.5 |
C11—C12—H12A | 109.5 | C31—C33—H33C | 109.5 |
C11—C12—H12B | 109.5 | H33A—C33—H33C | 109.5 |
H12A—C12—H12B | 109.5 | H33B—C33—H33C | 109.5 |
C11—C12—H12C | 109.5 | C31—C34—H34A | 109.5 |
H12A—C12—H12C | 109.5 | C31—C34—H34B | 109.5 |
H12B—C12—H12C | 109.5 | H34A—C34—H34B | 109.5 |
C11—C13—H13A | 109.5 | C31—C34—H34C | 109.5 |
C11—C13—H13B | 109.5 | H34A—C34—H34C | 109.5 |
H13A—C13—H13B | 109.5 | H34B—C34—H34C | 109.5 |
C11—C13—H13C | 109.5 | C37—C35—C36 | 108.51 (16) |
H13A—C13—H13C | 109.5 | C37—C35—C38 | 108.29 (18) |
H13B—C13—H13C | 109.5 | C36—C35—C38 | 108.12 (17) |
C11—C14—H14A | 109.5 | C37—C35—Si2 | 111.45 (15) |
C11—C14—H14B | 109.5 | C36—C35—Si2 | 113.31 (15) |
H14A—C14—H14B | 109.5 | C38—C35—Si2 | 106.99 (13) |
C11—C14—H14C | 109.5 | C35—C36—H36A | 109.5 |
H14A—C14—H14C | 109.5 | C35—C36—H36B | 109.5 |
H14B—C14—H14C | 109.5 | H36A—C36—H36B | 109.5 |
C17—C15—C18 | 108.54 (17) | C35—C36—H36C | 109.5 |
C17—C15—C16 | 108.67 (18) | H36A—C36—H36C | 109.5 |
C18—C15—C16 | 107.65 (19) | H36B—C36—H36C | 109.5 |
C17—C15—Si1 | 113.11 (16) | C35—C37—H37A | 109.5 |
C18—C15—Si1 | 110.18 (14) | C35—C37—H37B | 109.5 |
C16—C15—Si1 | 108.54 (15) | H37A—C37—H37B | 109.5 |
C15—C16—H16A | 109.5 | C35—C37—H37C | 109.5 |
C15—C16—H16B | 109.5 | H37A—C37—H37C | 109.5 |
H16A—C16—H16B | 109.5 | H37B—C37—H37C | 109.5 |
C15—C16—H16C | 109.5 | C35—C38—H38A | 109.5 |
H16A—C16—H16C | 109.5 | C35—C38—H38B | 109.5 |
H16B—C16—H16C | 109.5 | H38A—C38—H38B | 109.5 |
C15—C17—H17A | 109.5 | C35—C38—H38C | 109.5 |
C15—C17—H17B | 109.5 | H38A—C38—H38C | 109.5 |
H17A—C17—H17B | 109.5 | H38B—C38—H38C | 109.5 |
F1—Si1—C1—C2 | 13.58 (19) | F2—Si2—C21—C22 | 7.40 (19) |
C15—Si1—C1—C2 | 126.97 (18) | C31—Si2—C21—C22 | 120.43 (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—C6 | 80.4 (2) | C35—Si2—C21—C26 | 75.4 (2) |
C6—C1—C2—C3 | −0.2 (3) | C26—C21—C22—C23 | −0.7 (3) |
Si1—C1—C2—C3 | 179.61 (17) | Si2—C21—C22—C23 | −179.99 (17) |
C1—C2—C3—C4 | 0.9 (3) | C21—C22—C23—C24 | 0.6 (3) |
C2—C3—C4—C5 | −0.6 (3) | C22—C23—C24—C25 | 0.4 (3) |
C2—C3—C4—C7 | 179.7 (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—C6 | 179.4 (2) | C27—C24—C25—C26 | 178.2 (2) |
C4—C5—C6—C1 | 0.9 (3) | C24—C25—C26—C21 | 1.1 (3) |
C2—C1—C6—C5 | −0.6 (3) | C22—C21—C26—C25 | −0.1 (3) |
Si1—C1—C6—C5 | 179.53 (17) | Si2—C21—C26—C25 | 179.14 (18) |
C5—C4—C7—O7 | 14.0 (3) | C23—C24—C27—O27 | −141.9 (2) |
C3—C4—C7—O7 | −166.4 (2) | C25—C24—C27—O27 | 38.8 (3) |
F1—Si1—C11—C14 | 72.77 (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—C34 | 70.95 (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—C32 | 79.72 (17) |
C15—Si1—C11—C13 | 78.40 (16) | C35—Si2—C31—C32 | −50.43 (18) |
F1—Si1—C11—C12 | −46.82 (14) | F2—Si2—C31—C33 | 71.93 (16) |
C1—Si1—C11—C12 | 65.68 (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—C17 | 84.19 (17) | C21—Si2—C35—C37 | −54.03 (15) |
C11—Si1—C15—C17 | −45.33 (17) | C31—Si2—C35—C37 | 76.69 (16) |
F1—Si1—C15—C18 | −40.80 (17) | F2—Si2—C35—C36 | 71.20 (14) |
C1—Si1—C15—C18 | −154.13 (14) | C21—Si2—C35—C36 | −176.76 (13) |
C11—Si1—C15—C18 | 76.35 (17) | C31—Si2—C35—C36 | −46.05 (17) |
F1—Si1—C15—C16 | 76.84 (14) | F2—Si2—C35—C38 | −47.87 (15) |
C1—Si1—C15—C16 | −36.49 (17) | C21—Si2—C35—C38 | 64.17 (15) |
C11—Si1—C15—C16 | −166.01 (13) | C31—Si2—C35—C38 | −165.11 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O27i | 0.74 (5) | 2.01 (5) | 2.707 (3) | 157 (5) |
O27—H27A···O27ii | 0.76 (3) | 2.00 (3) | 2.727 (3) | 160 (5) |
O7—H7B···O7iii | 0.70 (4) | 2.14 (3) | 2.787 (4) | 154 (5) |
O27—H27B···O7iv | 0.80 (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. |
Experimental details
Crystal data | |
Chemical formula | C15H25FOSi |
Mr | 268.44 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 8.3213 (5), 12.4011 (7), 17.1036 (9) |
α, β, γ (°) | 103.581 (5), 101.553 (5), 107.487 (5) |
V (Å3) | 1564.96 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.26 × 0.14 × 0.12 |
Data collection | |
Diffractometer | Xcalibur2 CCD diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2008) |
Tmin, Tmax | 0.928, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5698, 5698, 3074 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.070, 0.81 |
No. of reflections | 5698 |
No. of parameters | 337 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.24 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O27i | 0.74 (5) | 2.01 (5) | 2.707 (3) | 157 (5) |
O27—H27A···O27ii | 0.76 (3) | 2.00 (3) | 2.727 (3) | 160 (5) |
O7—H7B···O7iii | 0.70 (4) | 2.14 (3) | 2.787 (4) | 154 (5) |
O27—H27B···O7iv | 0.80 (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. |
References
Bradtmöller, G., Jurkschat, K. & Schürmann, M. (2006). Acta Cryst. E62, o1393–o1394. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Iovkova, L., Wängler, B., Schirrmacher, E., Schirrmacher, R., Quandt, G., Boening, G., Schürmann, M. & Jurkschat, K. (2009). Chem. Eur. J. 15, 2140–2147. Web of Science CSD CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.