Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029405/cf6456sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029405/cf6456Isup2.hkl |
CCDC reference: 287499
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.112
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Si2 PLAT396_ALERT_2_C Deviating Si-O-Si Angle from 150 Deg for O1 164.20 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
The crystal used for this study was obtained in low yield (<10%) from dimethylmethoxy(2-pyridyl)silane and triphenylsilanol. A subsequently optimized synthesis is described. Ph3SiOH (0.915 g, 3.3 mmol) in tetrahydrofuran (20 ml) was treated with SiMe2Cl2 (0.21 g, 1.65 mmol) in the presence of pyridine (1 ml). The reaction mixture was dried in vacuo and the residue was extracted with hexanes (20 ml). After concentration of the extract, pure colorless crystals of the title compund were formed (0.51 g, 0.84 mmol, 51%).
H-atoms were placed in calculated positions, with C—H distances 0.95 (aromatic) and 0.98 Å (CH3), and with Uiso(H) = 1.2Ueq(C), and refined as riding, with a rigid rotator model for CH3.
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
C38H36O2Si3 | F(000) = 3864 |
Mr = 608.94 | Least Squares Treatment of 25 SET4 setting angles. |
Monoclinic, C2/c | Dx = 1.216 Mg m−3 |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 47.7051 (5) Å | Cell parameters from 11325 reflections |
b = 7.6270 (1) Å | θ = 1.0–27.5° |
c = 33.1200 (5) Å | µ = 0.18 mm−1 |
β = 124.1246 (6)° | T = 150 K |
V = 9975.7 (2) Å3 | Plate, colorless |
Z = 12 | 0.30 × 0.27 × 0.09 mm |
Nonius KappaCCD diffractometer | 7490 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.066 |
Graphite monochromator | θmax = 27.4°, θmin = 1.0° |
Detector resolution: 18.4 pixels mm-1 | h = −60→61 |
ω and ϕ scans | k = −9→9 |
43681 measured reflections | l = −40→42 |
11325 independent 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0388P)2 + 6.4055P] where P = (Fo2 + 2Fc2)/3 |
11325 reflections | (Δ/σ)max = 0.001 |
585 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C38H36O2Si3 | V = 9975.7 (2) Å3 |
Mr = 608.94 | Z = 12 |
Monoclinic, C2/c | Mo Kα radiation |
a = 47.7051 (5) Å | µ = 0.18 mm−1 |
b = 7.6270 (1) Å | T = 150 K |
c = 33.1200 (5) Å | 0.30 × 0.27 × 0.09 mm |
β = 124.1246 (6)° |
Nonius KappaCCD diffractometer | 7490 reflections with I > 2σ(I) |
43681 measured reflections | Rint = 0.066 |
11325 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.36 e Å−3 |
11325 reflections | Δρmin = −0.31 e Å−3 |
585 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
Si1 | 0.21757 (1) | 0.93704 (7) | 0.08503 (2) | 0.0288 (2) | |
Si2 | 0.16404 (1) | 1.20332 (7) | 0.08047 (2) | 0.0262 (2) | |
Si3 | 0.10338 (1) | 0.99794 (7) | 0.07132 (2) | 0.0265 (2) | |
O1 | 0.19035 (4) | 1.05358 (19) | 0.08788 (6) | 0.0405 (5) | |
O2 | 0.12822 (3) | 1.10900 (17) | 0.06149 (5) | 0.0314 (4) | |
C1 | 0.18013 (7) | 1.3050 (4) | 0.13982 (10) | 0.0660 (11) | |
C2 | 0.15787 (6) | 1.3605 (3) | 0.03434 (10) | 0.0553 (9) | |
C11 | 0.23818 (5) | 0.7857 (3) | 0.13829 (7) | 0.0313 (7) | |
C12 | 0.24582 (6) | 0.8474 (3) | 0.18323 (8) | 0.0493 (9) | |
C13 | 0.26384 (7) | 0.7463 (4) | 0.22483 (9) | 0.0602 (10) | |
C14 | 0.27468 (6) | 0.5809 (4) | 0.22301 (9) | 0.0524 (9) | |
C15 | 0.26718 (6) | 0.5164 (3) | 0.17929 (9) | 0.0467 (9) | |
C16 | 0.24906 (5) | 0.6173 (3) | 0.13742 (8) | 0.0384 (7) | |
C21 | 0.25160 (5) | 1.0801 (3) | 0.09126 (7) | 0.0292 (6) | |
C22 | 0.28530 (6) | 1.0600 (3) | 0.13014 (8) | 0.0417 (8) | |
C23 | 0.31055 (6) | 1.1680 (4) | 0.13585 (9) | 0.0544 (9) | |
C24 | 0.30251 (6) | 1.2991 (3) | 0.10250 (10) | 0.0510 (9) | |
C25 | 0.26949 (6) | 1.3217 (3) | 0.06314 (9) | 0.0458 (9) | |
C26 | 0.24431 (6) | 1.2126 (3) | 0.05773 (8) | 0.0377 (8) | |
C31 | 0.19521 (5) | 0.8179 (3) | 0.02576 (7) | 0.0305 (6) | |
C32 | 0.21320 (6) | 0.7361 (3) | 0.00915 (8) | 0.0430 (8) | |
C33 | 0.19698 (7) | 0.6385 (3) | −0.03342 (9) | 0.0534 (9) | |
C34 | 0.16230 (7) | 0.6228 (3) | −0.06062 (9) | 0.0512 (9) | |
C35 | 0.14378 (6) | 0.7028 (3) | −0.04552 (8) | 0.0478 (8) | |
C36 | 0.16011 (5) | 0.7989 (3) | −0.00266 (8) | 0.0374 (7) | |
C41 | 0.12807 (5) | 0.8911 (3) | 0.13269 (7) | 0.0295 (6) | |
C42 | 0.11778 (6) | 0.8993 (3) | 0.16466 (8) | 0.0403 (8) | |
C43 | 0.13575 (7) | 0.8163 (3) | 0.20936 (8) | 0.0489 (9) | |
C44 | 0.16432 (6) | 0.7211 (3) | 0.22331 (8) | 0.0471 (8) | |
C45 | 0.17532 (6) | 0.7106 (3) | 0.19272 (8) | 0.0414 (7) | |
C46 | 0.15741 (5) | 0.7956 (3) | 0.14791 (8) | 0.0351 (7) | |
C51 | 0.07199 (5) | 1.1542 (3) | 0.06818 (7) | 0.0276 (6) | |
C52 | 0.03746 (5) | 1.1471 (3) | 0.03205 (7) | 0.0295 (6) | |
C53 | 0.01501 (5) | 1.2697 (3) | 0.02989 (8) | 0.0344 (7) | |
C54 | 0.02687 (6) | 1.4013 (3) | 0.06419 (8) | 0.0369 (8) | |
C55 | 0.06100 (6) | 1.4117 (3) | 0.10064 (8) | 0.0398 (8) | |
C56 | 0.08329 (6) | 1.2892 (3) | 0.10257 (8) | 0.0360 (7) | |
C61 | 0.08224 (5) | 0.8321 (3) | 0.02176 (7) | 0.0268 (6) | |
C62 | 0.08465 (5) | 0.6517 (3) | 0.03032 (8) | 0.0357 (7) | |
C63 | 0.07039 (6) | 0.5320 (3) | −0.00781 (9) | 0.0426 (8) | |
C64 | 0.05357 (6) | 0.5898 (3) | −0.05518 (9) | 0.0431 (8) | |
C65 | 0.05024 (6) | 0.7674 (3) | −0.06489 (8) | 0.0412 (8) | |
C66 | 0.06459 (5) | 0.8860 (3) | −0.02699 (8) | 0.0351 (7) | |
Si4 | 0.05770 (1) | 0.58038 (7) | 0.26019 (2) | 0.0243 (2) | |
Si5 | 0.00000 | 0.33836 (9) | 0.25000 | 0.0234 (2) | |
O3 | 0.02398 (3) | 0.46381 (16) | 0.24161 (5) | 0.0276 (4) | |
C3 | 0.02646 (6) | 0.2052 (3) | 0.30502 (8) | 0.0414 (8) | |
C71 | 0.07144 (5) | 0.6937 (2) | 0.31855 (7) | 0.0269 (6) | |
C72 | 0.04964 (5) | 0.7226 (3) | 0.33323 (7) | 0.0306 (7) | |
C73 | 0.06014 (6) | 0.8095 (3) | 0.37615 (8) | 0.0349 (7) | |
C74 | 0.09282 (6) | 0.8712 (3) | 0.40567 (8) | 0.0394 (8) | |
C75 | 0.11484 (6) | 0.8452 (4) | 0.39206 (9) | 0.0573 (9) | |
C76 | 0.10430 (6) | 0.7576 (4) | 0.34919 (8) | 0.0493 (9) | |
C81 | 0.09287 (5) | 0.4354 (2) | 0.27077 (7) | 0.0270 (6) | |
C82 | 0.10700 (5) | 0.3121 (3) | 0.30845 (8) | 0.0381 (8) | |
C83 | 0.13310 (6) | 0.2034 (3) | 0.31717 (9) | 0.0487 (8) | |
C84 | 0.14572 (6) | 0.2136 (3) | 0.28883 (9) | 0.0476 (9) | |
C85 | 0.13223 (6) | 0.3334 (3) | 0.25146 (9) | 0.0449 (8) | |
C86 | 0.10621 (5) | 0.4431 (3) | 0.24275 (8) | 0.0347 (7) | |
C91 | 0.04681 (5) | 0.7432 (2) | 0.21130 (7) | 0.0246 (6) | |
C92 | 0.05670 (5) | 0.9183 (3) | 0.22156 (8) | 0.0341 (7) | |
C93 | 0.04870 (6) | 1.0362 (3) | 0.18475 (9) | 0.0427 (8) | |
C94 | 0.03049 (6) | 0.9840 (3) | 0.13689 (8) | 0.0375 (8) | |
C95 | 0.02036 (6) | 0.8118 (3) | 0.12567 (8) | 0.0370 (7) | |
C96 | 0.02836 (5) | 0.6925 (3) | 0.16220 (7) | 0.0317 (7) | |
H1A | 0.18190 | 1.21610 | 0.16250 | 0.0990* | |
H1B | 0.16460 | 1.39790 | 0.13590 | 0.0990* | |
H1C | 0.20250 | 1.35540 | 0.15280 | 0.0990* | |
H2A | 0.17950 | 1.41750 | 0.04550 | 0.0830* | |
H2B | 0.14130 | 1.44930 | 0.02920 | 0.0830* | |
H2C | 0.14950 | 1.29890 | 0.00360 | 0.0830* | |
H12 | 0.23850 | 0.96110 | 0.18510 | 0.0590* | |
H13 | 0.26880 | 0.79100 | 0.25490 | 0.0720* | |
H14 | 0.28720 | 0.51200 | 0.25180 | 0.0630* | |
H15 | 0.27450 | 0.40210 | 0.17780 | 0.0560* | |
H16 | 0.24390 | 0.57050 | 0.10740 | 0.0460* | |
H22 | 0.29110 | 0.96970 | 0.15330 | 0.0500* | |
H23 | 0.33330 | 1.15180 | 0.16270 | 0.0650* | |
H24 | 0.31980 | 1.37450 | 0.10660 | 0.0610* | |
H25 | 0.26410 | 1.41130 | 0.03990 | 0.0550* | |
H26 | 0.22160 | 1.22850 | 0.03060 | 0.0450* | |
H32 | 0.23710 | 0.74790 | 0.02750 | 0.0520* | |
H33 | 0.20970 | 0.58280 | −0.04380 | 0.0640* | |
H34 | 0.15110 | 0.55650 | −0.09000 | 0.0610* | |
H35 | 0.11980 | 0.69190 | −0.06450 | 0.0570* | |
H36 | 0.14710 | 0.85300 | 0.00760 | 0.0450* | |
H42 | 0.09800 | 0.96340 | 0.15540 | 0.0480* | |
H43 | 0.12840 | 0.82510 | 0.23060 | 0.0590* | |
H44 | 0.17640 | 0.66270 | 0.25390 | 0.0570* | |
H45 | 0.19510 | 0.64540 | 0.20230 | 0.0500* | |
H46 | 0.16530 | 0.78880 | 0.12720 | 0.0420* | |
H52 | 0.02900 | 1.05650 | 0.00830 | 0.0350* | |
H53 | −0.00840 | 1.26260 | 0.00480 | 0.0410* | |
H54 | 0.01160 | 1.48490 | 0.06280 | 0.0440* | |
H55 | 0.06920 | 1.50240 | 0.12430 | 0.0480* | |
H56 | 0.10670 | 1.29740 | 0.12780 | 0.0430* | |
H62 | 0.09630 | 0.61000 | 0.06290 | 0.0430* | |
H63 | 0.07230 | 0.40990 | −0.00110 | 0.0510* | |
H64 | 0.04430 | 0.50780 | −0.08120 | 0.0520* | |
H65 | 0.03810 | 0.80770 | −0.09770 | 0.0490* | |
H66 | 0.06240 | 1.00780 | −0.03410 | 0.0420* | |
H3A | 0.04030 | 0.12490 | 0.30010 | 0.0620* | |
H3B | 0.01200 | 0.13730 | 0.31150 | 0.0620* | |
H3C | 0.04120 | 0.28210 | 0.33280 | 0.0620* | |
H72 | 0.02700 | 0.68150 | 0.31330 | 0.0370* | |
H73 | 0.04470 | 0.82690 | 0.38530 | 0.0420* | |
H74 | 0.10000 | 0.93110 | 0.43510 | 0.0470* | |
H75 | 0.13740 | 0.88740 | 0.41210 | 0.0690* | |
H76 | 0.11990 | 0.74060 | 0.34040 | 0.0590* | |
H82 | 0.09860 | 0.30260 | 0.32840 | 0.0460* | |
H83 | 0.14240 | 0.12080 | 0.34310 | 0.0580* | |
H84 | 0.16360 | 0.13860 | 0.29500 | 0.0570* | |
H85 | 0.14070 | 0.34110 | 0.23160 | 0.0540* | |
H86 | 0.09730 | 0.52590 | 0.21690 | 0.0420* | |
H92 | 0.06920 | 0.95750 | 0.25440 | 0.0410* | |
H93 | 0.05590 | 1.15460 | 0.19280 | 0.0510* | |
H94 | 0.02490 | 1.06570 | 0.11180 | 0.0450* | |
H95 | 0.00780 | 0.77450 | 0.09260 | 0.0440* | |
H96 | 0.02120 | 0.57410 | 0.15380 | 0.0380* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.0251 (3) | 0.0311 (3) | 0.0320 (3) | 0.0042 (2) | 0.0172 (3) | 0.0021 (3) |
Si2 | 0.0247 (3) | 0.0244 (3) | 0.0304 (3) | −0.0002 (2) | 0.0160 (3) | −0.0008 (2) |
Si3 | 0.0246 (3) | 0.0289 (3) | 0.0285 (3) | 0.0010 (2) | 0.0164 (3) | 0.0030 (2) |
O1 | 0.0350 (9) | 0.0413 (9) | 0.0550 (10) | 0.0110 (7) | 0.0313 (8) | 0.0087 (8) |
O2 | 0.0242 (7) | 0.0371 (8) | 0.0343 (8) | −0.0014 (6) | 0.0173 (7) | 0.0041 (6) |
C1 | 0.0628 (19) | 0.079 (2) | 0.0629 (18) | −0.0296 (16) | 0.0394 (16) | −0.0404 (16) |
C2 | 0.0432 (15) | 0.0511 (15) | 0.0713 (18) | 0.0055 (12) | 0.0319 (14) | 0.0267 (14) |
C11 | 0.0257 (11) | 0.0358 (12) | 0.0343 (12) | 0.0034 (9) | 0.0180 (10) | 0.0046 (10) |
C12 | 0.0535 (16) | 0.0560 (16) | 0.0376 (14) | 0.0231 (13) | 0.0250 (13) | 0.0072 (12) |
C13 | 0.0598 (17) | 0.085 (2) | 0.0354 (14) | 0.0295 (16) | 0.0265 (14) | 0.0149 (14) |
C14 | 0.0419 (15) | 0.0668 (18) | 0.0458 (15) | 0.0181 (13) | 0.0230 (13) | 0.0257 (14) |
C15 | 0.0448 (15) | 0.0354 (13) | 0.0597 (17) | 0.0078 (11) | 0.0292 (13) | 0.0123 (12) |
C16 | 0.0392 (13) | 0.0338 (12) | 0.0420 (13) | 0.0008 (10) | 0.0226 (12) | 0.0003 (10) |
C21 | 0.0272 (11) | 0.0319 (11) | 0.0328 (11) | 0.0019 (9) | 0.0195 (10) | −0.0046 (9) |
C22 | 0.0332 (13) | 0.0500 (14) | 0.0414 (13) | −0.0027 (11) | 0.0207 (11) | −0.0026 (11) |
C23 | 0.0334 (14) | 0.0749 (19) | 0.0478 (15) | −0.0135 (13) | 0.0185 (12) | −0.0074 (14) |
C24 | 0.0442 (15) | 0.0517 (16) | 0.0655 (18) | −0.0194 (12) | 0.0359 (14) | −0.0187 (14) |
C25 | 0.0526 (16) | 0.0369 (13) | 0.0627 (17) | −0.0031 (11) | 0.0414 (15) | −0.0001 (12) |
C26 | 0.0343 (13) | 0.0391 (13) | 0.0435 (13) | 0.0012 (10) | 0.0242 (11) | −0.0003 (11) |
C31 | 0.0274 (11) | 0.0312 (11) | 0.0313 (11) | 0.0002 (9) | 0.0155 (10) | 0.0057 (9) |
C32 | 0.0349 (13) | 0.0561 (15) | 0.0380 (13) | −0.0060 (11) | 0.0204 (11) | −0.0082 (11) |
C33 | 0.0549 (17) | 0.0650 (17) | 0.0428 (15) | −0.0074 (14) | 0.0290 (14) | −0.0136 (13) |
C34 | 0.0557 (17) | 0.0514 (15) | 0.0332 (13) | −0.0101 (13) | 0.0168 (13) | −0.0058 (11) |
C35 | 0.0327 (13) | 0.0479 (15) | 0.0407 (14) | −0.0055 (11) | 0.0071 (12) | 0.0068 (12) |
C36 | 0.0318 (12) | 0.0343 (12) | 0.0394 (13) | 0.0008 (10) | 0.0158 (11) | 0.0078 (10) |
C41 | 0.0299 (11) | 0.0283 (11) | 0.0305 (11) | −0.0008 (9) | 0.0170 (10) | 0.0022 (9) |
C42 | 0.0426 (14) | 0.0453 (14) | 0.0400 (13) | −0.0002 (11) | 0.0275 (12) | 0.0041 (11) |
C43 | 0.0617 (17) | 0.0526 (16) | 0.0385 (14) | −0.0070 (13) | 0.0319 (14) | 0.0052 (12) |
C44 | 0.0589 (17) | 0.0365 (13) | 0.0317 (13) | −0.0070 (12) | 0.0167 (13) | 0.0062 (10) |
C45 | 0.0392 (13) | 0.0303 (12) | 0.0365 (13) | 0.0042 (10) | 0.0101 (11) | 0.0018 (10) |
C46 | 0.0378 (13) | 0.0328 (12) | 0.0321 (12) | 0.0007 (10) | 0.0180 (11) | 0.0001 (10) |
C51 | 0.0289 (11) | 0.0294 (11) | 0.0301 (11) | 0.0010 (9) | 0.0200 (10) | 0.0058 (9) |
C52 | 0.0315 (11) | 0.0267 (10) | 0.0335 (11) | 0.0000 (9) | 0.0202 (10) | 0.0021 (9) |
C53 | 0.0306 (12) | 0.0334 (12) | 0.0414 (13) | 0.0056 (10) | 0.0215 (11) | 0.0102 (10) |
C54 | 0.0423 (14) | 0.0325 (12) | 0.0492 (14) | 0.0084 (10) | 0.0338 (12) | 0.0073 (11) |
C55 | 0.0501 (15) | 0.0352 (12) | 0.0440 (14) | −0.0004 (11) | 0.0325 (13) | −0.0052 (10) |
C56 | 0.0339 (12) | 0.0397 (13) | 0.0356 (12) | 0.0009 (10) | 0.0203 (11) | −0.0011 (10) |
C61 | 0.0239 (10) | 0.0313 (11) | 0.0312 (11) | 0.0003 (9) | 0.0191 (9) | 0.0016 (9) |
C62 | 0.0326 (12) | 0.0338 (12) | 0.0372 (12) | −0.0009 (10) | 0.0175 (11) | 0.0063 (10) |
C63 | 0.0414 (14) | 0.0285 (12) | 0.0549 (16) | −0.0023 (10) | 0.0252 (13) | −0.0024 (11) |
C64 | 0.0390 (14) | 0.0470 (14) | 0.0447 (14) | −0.0049 (11) | 0.0243 (12) | −0.0167 (12) |
C65 | 0.0455 (14) | 0.0496 (15) | 0.0335 (12) | 0.0041 (11) | 0.0253 (12) | −0.0002 (11) |
C66 | 0.0450 (14) | 0.0320 (12) | 0.0368 (12) | 0.0029 (10) | 0.0282 (11) | 0.0025 (10) |
Si4 | 0.0250 (3) | 0.0255 (3) | 0.0237 (3) | 0.0007 (2) | 0.0145 (2) | 0.0006 (2) |
Si5 | 0.0279 (4) | 0.0211 (4) | 0.0237 (4) | 0.0000 | 0.0160 (4) | 0.0000 |
O3 | 0.0270 (7) | 0.0286 (7) | 0.0284 (7) | −0.0010 (6) | 0.0163 (6) | 0.0022 (6) |
C3 | 0.0442 (14) | 0.0425 (13) | 0.0435 (13) | 0.0102 (11) | 0.0283 (12) | 0.0182 (11) |
C71 | 0.0281 (11) | 0.0271 (10) | 0.0257 (10) | 0.0016 (9) | 0.0153 (9) | 0.0020 (9) |
C72 | 0.0333 (12) | 0.0270 (11) | 0.0341 (12) | −0.0033 (9) | 0.0205 (10) | −0.0048 (9) |
C73 | 0.0436 (14) | 0.0300 (11) | 0.0409 (13) | −0.0007 (10) | 0.0297 (12) | −0.0043 (10) |
C74 | 0.0411 (14) | 0.0471 (14) | 0.0308 (12) | −0.0044 (11) | 0.0206 (11) | −0.0106 (10) |
C75 | 0.0361 (14) | 0.092 (2) | 0.0420 (14) | −0.0168 (14) | 0.0208 (12) | −0.0293 (14) |
C76 | 0.0326 (13) | 0.0806 (18) | 0.0402 (14) | −0.0102 (12) | 0.0237 (12) | −0.0195 (13) |
C81 | 0.0250 (11) | 0.0266 (10) | 0.0277 (10) | −0.0025 (8) | 0.0137 (9) | −0.0025 (9) |
C82 | 0.0344 (13) | 0.0410 (13) | 0.0373 (13) | 0.0058 (10) | 0.0191 (11) | 0.0079 (10) |
C83 | 0.0392 (14) | 0.0413 (14) | 0.0535 (15) | 0.0136 (11) | 0.0186 (13) | 0.0117 (12) |
C84 | 0.0345 (13) | 0.0397 (14) | 0.0621 (17) | 0.0078 (11) | 0.0231 (13) | −0.0093 (13) |
C85 | 0.0412 (14) | 0.0483 (14) | 0.0540 (15) | 0.0016 (12) | 0.0320 (13) | −0.0087 (12) |
C86 | 0.0344 (12) | 0.0363 (12) | 0.0358 (12) | 0.0011 (10) | 0.0211 (11) | −0.0010 (10) |
C91 | 0.0240 (10) | 0.0252 (10) | 0.0295 (11) | 0.0009 (8) | 0.0181 (9) | 0.0015 (8) |
C92 | 0.0407 (13) | 0.0287 (11) | 0.0366 (12) | −0.0049 (10) | 0.0239 (11) | −0.0038 (10) |
C93 | 0.0535 (15) | 0.0261 (12) | 0.0580 (16) | −0.0024 (10) | 0.0370 (14) | 0.0043 (11) |
C94 | 0.0437 (14) | 0.0359 (12) | 0.0455 (14) | 0.0112 (10) | 0.0327 (12) | 0.0155 (11) |
C95 | 0.0419 (13) | 0.0403 (13) | 0.0297 (11) | 0.0056 (10) | 0.0207 (11) | 0.0054 (10) |
C96 | 0.0390 (12) | 0.0256 (11) | 0.0323 (11) | 0.0007 (9) | 0.0211 (10) | 0.0021 (9) |
Si1—O1 | 1.619 (2) | C14—H14 | 0.950 |
Si1—C11 | 1.861 (2) | C15—H15 | 0.950 |
Si1—C21 | 1.869 (3) | C16—H16 | 0.950 |
Si1—C31 | 1.862 (2) | C22—H22 | 0.950 |
Si2—O1 | 1.611 (2) | C23—H23 | 0.950 |
Si2—O2 | 1.6209 (17) | C24—H24 | 0.950 |
Si2—C1 | 1.834 (3) | C25—H25 | 0.950 |
Si2—C2 | 1.831 (3) | C26—H26 | 0.950 |
Si3—O2 | 1.6312 (17) | C32—H32 | 0.950 |
Si3—C41 | 1.870 (2) | C33—H33 | 0.950 |
Si3—C51 | 1.871 (3) | C34—H34 | 0.950 |
Si3—C61 | 1.859 (2) | C35—H35 | 0.950 |
Si4—C71 | 1.869 (2) | C36—H36 | 0.950 |
Si4—C81 | 1.871 (2) | C42—H42 | 0.950 |
Si4—O3 | 1.6268 (17) | C43—H43 | 0.950 |
Si4—C91 | 1.8680 (19) | C44—H44 | 0.950 |
Si5—O3i | 1.6303 (16) | C45—H45 | 0.950 |
Si5—C3i | 1.834 (2) | C46—H46 | 0.950 |
Si5—O3 | 1.6303 (16) | C52—H52 | 0.950 |
Si5—C3 | 1.834 (2) | C53—H53 | 0.950 |
C11—C12 | 1.400 (3) | C54—H54 | 0.950 |
C11—C16 | 1.392 (3) | C55—H55 | 0.950 |
C12—C13 | 1.380 (3) | C56—H56 | 0.950 |
C13—C14 | 1.378 (4) | C62—H62 | 0.950 |
C14—C15 | 1.373 (4) | C63—H63 | 0.950 |
C15—C16 | 1.385 (3) | C64—H64 | 0.950 |
C21—C26 | 1.394 (3) | C65—H65 | 0.950 |
C21—C22 | 1.394 (4) | C66—H66 | 0.950 |
C22—C23 | 1.382 (4) | C71—C72 | 1.391 (4) |
C23—C24 | 1.375 (4) | C71—C76 | 1.393 (4) |
C24—C25 | 1.381 (4) | C72—C73 | 1.383 (3) |
C25—C26 | 1.388 (4) | C73—C74 | 1.378 (4) |
C31—C36 | 1.394 (4) | C74—C75 | 1.370 (5) |
C31—C32 | 1.399 (4) | C75—C76 | 1.384 (4) |
C32—C33 | 1.384 (3) | C81—C82 | 1.397 (3) |
C33—C34 | 1.375 (5) | C81—C86 | 1.390 (4) |
C34—C35 | 1.378 (5) | C82—C83 | 1.385 (4) |
C35—C36 | 1.385 (3) | C83—C84 | 1.372 (4) |
C41—C46 | 1.397 (4) | C84—C85 | 1.374 (3) |
C41—C42 | 1.396 (4) | C85—C86 | 1.387 (4) |
C42—C43 | 1.380 (3) | C91—C92 | 1.394 (3) |
C43—C44 | 1.375 (4) | C91—C96 | 1.401 (3) |
C44—C45 | 1.380 (4) | C92—C93 | 1.385 (3) |
C45—C46 | 1.389 (3) | C93—C94 | 1.371 (3) |
C51—C52 | 1.392 (3) | C94—C95 | 1.377 (3) |
C51—C56 | 1.400 (3) | C95—C96 | 1.385 (3) |
C52—C53 | 1.393 (4) | C3—H3A | 0.980 |
C53—C54 | 1.377 (3) | C3—H3B | 0.980 |
C54—C55 | 1.382 (4) | C3—H3C | 0.980 |
C55—C56 | 1.390 (4) | C72—H72 | 0.950 |
C61—C62 | 1.397 (3) | C73—H73 | 0.950 |
C61—C66 | 1.400 (3) | C74—H74 | 0.950 |
C62—C63 | 1.388 (3) | C75—H75 | 0.950 |
C63—C64 | 1.374 (3) | C76—H76 | 0.950 |
C64—C65 | 1.381 (3) | C82—H82 | 0.950 |
C65—C66 | 1.378 (3) | C83—H83 | 0.950 |
C1—H1A | 0.980 | C84—H84 | 0.950 |
C1—H1B | 0.980 | C85—H85 | 0.950 |
C1—H1C | 0.980 | C86—H86 | 0.950 |
C2—H2A | 0.980 | C92—H92 | 0.950 |
C2—H2B | 0.980 | C93—H93 | 0.950 |
C2—H2C | 0.980 | C94—H94 | 0.950 |
C12—H12 | 0.950 | C95—H95 | 0.950 |
C13—H13 | 0.950 | C96—H96 | 0.950 |
O1—Si1—C11 | 107.44 (11) | C25—C24—H24 | 120.0 |
O1—Si1—C21 | 110.39 (10) | C23—C24—H24 | 120.0 |
O1—Si1—C31 | 108.99 (11) | C24—C25—H25 | 120.0 |
C11—Si1—C21 | 107.04 (11) | C26—C25—H25 | 120.0 |
C11—Si1—C31 | 112.46 (10) | C25—C26—H26 | 119.0 |
C21—Si1—C31 | 110.47 (11) | C21—C26—H26 | 119.0 |
O1—Si2—O2 | 107.83 (9) | C31—C32—H32 | 119.0 |
O1—Si2—C1 | 108.35 (12) | C33—C32—H32 | 119.0 |
O1—Si2—C2 | 109.76 (12) | C32—C33—H33 | 120.0 |
O2—Si2—C1 | 108.65 (13) | C34—C33—H33 | 120.0 |
O2—Si2—C2 | 109.02 (11) | C35—C34—H34 | 120.0 |
C1—Si2—C2 | 113.09 (13) | C33—C34—H34 | 120.0 |
O2—Si3—C41 | 110.98 (10) | C34—C35—H35 | 120.0 |
O2—Si3—C51 | 107.86 (9) | C36—C35—H35 | 120.0 |
O2—Si3—C61 | 105.79 (10) | C31—C36—H36 | 119.0 |
C41—Si3—C51 | 109.55 (10) | C35—C36—H36 | 119.0 |
C41—Si3—C61 | 111.24 (10) | C41—C42—H42 | 119.0 |
C51—Si3—C61 | 111.33 (11) | C43—C42—H42 | 119.0 |
C81—Si4—C91 | 109.85 (11) | C44—C43—H43 | 120.0 |
C71—Si4—C91 | 110.78 (8) | C42—C43—H43 | 120.0 |
C71—Si4—C81 | 108.80 (10) | C43—C44—H44 | 120.0 |
O3—Si4—C71 | 110.03 (10) | C45—C44—H44 | 120.0 |
O3—Si4—C81 | 109.90 (8) | C44—C45—H45 | 120.0 |
O3—Si4—C91 | 107.48 (9) | C46—C45—H45 | 120.0 |
O3—Si5—C3i | 108.25 (10) | C41—C46—H46 | 119.0 |
O3i—Si5—C3 | 108.25 (10) | C45—C46—H46 | 119.0 |
C3—Si5—C3i | 112.76 (11) | C51—C52—H52 | 119.0 |
O3—Si5—O3i | 108.13 (8) | C53—C52—H52 | 119.0 |
O3—Si5—C3 | 109.67 (11) | C52—C53—H53 | 120.0 |
O3i—Si5—C3i | 109.67 (11) | C54—C53—H53 | 120.0 |
Si1—O1—Si2 | 164.17 (13) | C53—C54—H54 | 120.0 |
Si2—O2—Si3 | 151.51 (10) | C55—C54—H54 | 120.0 |
Si4—O3—Si5 | 153.62 (10) | C54—C55—H55 | 120.0 |
C12—C11—C16 | 117.0 (2) | C56—C55—H55 | 120.0 |
Si1—C11—C12 | 118.88 (17) | C55—C56—H56 | 119.0 |
Si1—C11—C16 | 123.89 (16) | C51—C56—H56 | 119.0 |
C11—C12—C13 | 121.2 (2) | C63—C62—H62 | 119.0 |
C12—C13—C14 | 120.5 (2) | C61—C62—H62 | 119.0 |
C13—C14—C15 | 119.5 (2) | C64—C63—H63 | 120.0 |
C14—C15—C16 | 120.3 (2) | C62—C63—H63 | 120.0 |
C11—C16—C15 | 121.5 (2) | C63—C64—H64 | 120.0 |
C22—C21—C26 | 117.3 (2) | C65—C64—H64 | 120.0 |
Si1—C21—C26 | 121.49 (19) | C66—C65—H65 | 120.0 |
Si1—C21—C22 | 121.20 (17) | C64—C65—H65 | 120.0 |
C21—C22—C23 | 121.7 (2) | C65—C66—H66 | 119.0 |
C22—C23—C24 | 119.6 (3) | C61—C66—H66 | 119.0 |
C23—C24—C25 | 120.4 (3) | Si4—C71—C72 | 122.54 (17) |
C24—C25—C26 | 119.6 (2) | Si4—C71—C76 | 120.9 (2) |
C21—C26—C25 | 121.4 (2) | C72—C71—C76 | 116.5 (2) |
Si1—C31—C36 | 121.56 (19) | C71—C72—C73 | 121.7 (2) |
Si1—C31—C32 | 121.14 (19) | C72—C73—C74 | 120.4 (3) |
C32—C31—C36 | 117.2 (2) | C73—C74—C75 | 119.2 (2) |
C31—C32—C33 | 121.6 (3) | C74—C75—C76 | 120.2 (3) |
C32—C33—C34 | 119.6 (3) | C71—C76—C75 | 122.0 (3) |
C33—C34—C35 | 120.3 (2) | Si4—C81—C82 | 119.85 (19) |
C34—C35—C36 | 120.0 (3) | Si4—C81—C86 | 123.24 (15) |
C31—C36—C35 | 121.3 (3) | C82—C81—C86 | 116.9 (2) |
Si3—C41—C46 | 120.80 (18) | C81—C82—C83 | 121.1 (2) |
Si3—C41—C42 | 121.99 (19) | C82—C83—C84 | 120.8 (2) |
C42—C41—C46 | 117.2 (2) | C83—C84—C85 | 119.4 (3) |
C41—C42—C43 | 121.5 (3) | C84—C85—C86 | 120.1 (3) |
C42—C43—C44 | 120.3 (3) | C81—C86—C85 | 121.8 (2) |
C43—C44—C45 | 119.8 (2) | Si4—C91—C92 | 122.29 (15) |
C44—C45—C46 | 119.9 (3) | Si4—C91—C96 | 120.71 (14) |
C41—C46—C45 | 121.3 (2) | C92—C91—C96 | 116.99 (18) |
Si3—C51—C52 | 123.20 (17) | C91—C92—C93 | 121.3 (2) |
Si3—C51—C56 | 119.51 (19) | C92—C93—C94 | 120.8 (2) |
C52—C51—C56 | 117.3 (2) | C93—C94—C95 | 119.2 (2) |
C51—C52—C53 | 121.5 (2) | C94—C95—C96 | 120.5 (2) |
C52—C53—C54 | 119.9 (2) | C91—C96—C95 | 121.2 (2) |
C53—C54—C55 | 120.0 (3) | Si5—C3—H3A | 109.0 |
C54—C55—C56 | 119.9 (2) | Si5—C3—H3B | 110.0 |
C51—C56—C55 | 121.4 (2) | Si5—C3—H3C | 109.0 |
Si3—C61—C66 | 119.74 (17) | H3A—C3—H3B | 109.0 |
Si3—C61—C62 | 123.31 (15) | H3A—C3—H3C | 110.0 |
C62—C61—C66 | 116.8 (2) | H3B—C3—H3C | 110.0 |
C61—C62—C63 | 121.4 (2) | C71—C72—H72 | 119.0 |
C62—C63—C64 | 120.1 (2) | C73—C72—H72 | 119.0 |
C63—C64—C65 | 119.9 (2) | C72—C73—H73 | 120.0 |
C64—C65—C66 | 119.9 (2) | C74—C73—H73 | 120.0 |
C61—C66—C65 | 121.9 (2) | C73—C74—H74 | 120.0 |
Si2—C1—H1A | 109.0 | C75—C74—H74 | 120.0 |
Si2—C1—H1C | 110.0 | C74—C75—H75 | 120.0 |
H1A—C1—H1B | 110.0 | C76—C75—H75 | 120.0 |
Si2—C1—H1B | 109.0 | C71—C76—H76 | 119.0 |
H1B—C1—H1C | 109.0 | C75—C76—H76 | 119.0 |
H1A—C1—H1C | 109.0 | C81—C82—H82 | 120.0 |
Si2—C2—H2C | 110.0 | C83—C82—H82 | 119.0 |
Si2—C2—H2B | 109.0 | C82—C83—H83 | 120.0 |
Si2—C2—H2A | 109.0 | C84—C83—H83 | 120.0 |
H2B—C2—H2C | 109.0 | C83—C84—H84 | 120.0 |
H2A—C2—H2B | 110.0 | C85—C84—H84 | 120.0 |
H2A—C2—H2C | 109.0 | C84—C85—H85 | 120.0 |
C11—C12—H12 | 119.0 | C86—C85—H85 | 120.0 |
C13—C12—H12 | 119.0 | C81—C86—H86 | 119.0 |
C12—C13—H13 | 120.0 | C85—C86—H86 | 119.0 |
C14—C13—H13 | 120.0 | C91—C92—H92 | 119.0 |
C13—C14—H14 | 120.0 | C93—C92—H92 | 119.0 |
C15—C14—H14 | 120.0 | C92—C93—H93 | 120.0 |
C16—C15—H15 | 120.0 | C94—C93—H93 | 120.0 |
C14—C15—H15 | 120.0 | C93—C94—H94 | 120.0 |
C11—C16—H16 | 119.0 | C95—C94—H94 | 120.0 |
C15—C16—H16 | 119.0 | C94—C95—H95 | 120.0 |
C21—C22—H22 | 119.0 | C96—C95—H95 | 120.0 |
C23—C22—H22 | 119.0 | C91—C96—H96 | 119.0 |
C24—C23—H23 | 120.0 | C95—C96—H96 | 119.0 |
C22—C23—H23 | 120.0 |
Symmetry code: (i) −x, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C38H36O2Si3 |
Mr | 608.94 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 150 |
a, b, c (Å) | 47.7051 (5), 7.6270 (1), 33.1200 (5) |
β (°) | 124.1246 (6) |
V (Å3) | 9975.7 (2) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.30 × 0.27 × 0.09 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 43681, 11325, 7490 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.112, 1.02 |
No. of reflections | 11325 |
No. of parameters | 585 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.31 |
Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), DENZO, SHELXS86 (Sheldrick, 1985), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
Si1—O1 | 1.619 (2) | Si3—O2 | 1.6312 (17) |
Si2—O1 | 1.611 (2) | Si4—O3 | 1.6268 (17) |
Si2—O2 | 1.6209 (17) | Si5—O3 | 1.6303 (16) |
Si2—C1 | 1.834 (3) | Si5—C3 | 1.834 (2) |
Si2—C2 | 1.831 (3) | ||
O1—Si2—O2 | 107.83 (9) | C3—Si5—C3i | 112.76 (11) |
O1—Si2—C1 | 108.35 (12) | O3—Si5—O3i | 108.13 (8) |
O1—Si2—C2 | 109.76 (12) | O3—Si5—C3 | 109.67 (11) |
O2—Si2—C1 | 108.65 (13) | O3i—Si5—C3i | 109.67 (11) |
O2—Si2—C2 | 109.02 (11) | Si1—O1—Si2 | 164.17 (13) |
C1—Si2—C2 | 113.09 (13) | Si2—O2—Si3 | 151.51 (10) |
O3—Si5—C3i | 108.25 (10) | Si4—O3—Si5 | 153.62 (10) |
O3i—Si5—C3 | 108.25 (10) |
Symmetry code: (i) −x, y, −z+1/2. |
The symmetrical title compound, (I), was obtained unintentially in an attempt to synthesize the unsymmetrical compound 1,1-dimethyl-3,3,3-triphenyl-1-(2-pyridyl)disiloxane (i.e. with one of the two triphenylsiloxy groups substituted by a covalently bonded pyridyl group).
The unit cell contains eight equivalent molecules of (I) in general positions and four equivalent molecules located in positions with imposed crystallographic twofold rotation symmetry (Fig. 1). The two independent molecules have very similar conformations as illustrated by the quaternion fit (Mackay, 1984; Spek 2003) plot shown in Fig. 2. The approximate molecular twofold axes are approximately parallel to the monoclinic b axis.
The Si—O—Si angles range from 151.51 (10) to 164.17 (10)° (Table 1). Similar values in the range 160–163° have been reported by Graalmann et al. (1984) in the related siloxane structure 1,1,5,5-tetra-tert-butyl-1,5-dihydroxy-3,3-dimethyl-1,3,5-trisiloxane.
Molecules are stacked in planes parallel to (102) with an interplanar distance of approximately 8.3 Å (Fig. 3). Each layer contains the two types of molecules (general and special positions) in a 2:1 ratio.