Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054729/is2129sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054729/is2129IIsup2.hkl |
CCDC reference: 636707
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.091
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.809 0.972 Tmin(prime) and Tmax expected: 0.902 0.971 RR(prime) = 0.896 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C35 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.06
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.43 From the CIF: _reflns_number_total 5524 Count of symmetry unique reflns 3036 Completeness (_total/calc) 181.95% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2488 Fraction of Friedel pairs measured 0.819 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 5 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.
C27H38O4SSi | F(000) = 524 |
Mr = 486.72 | Dx = 1.196 Mg m−3 |
Monoclinic, P21 | Melting point: 349 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 14.2256 (15) Å | Cell parameters from 3893 reflections |
b = 6.4531 (7) Å | θ = 2.2–24.3° |
c = 15.0426 (16) Å | µ = 0.19 mm−1 |
β = 101.8651 (14)° | T = 193 K |
V = 1351.4 (2) Å3 | Prism, colorless |
Z = 2 | 0.52 × 0.41 × 0.15 mm |
SMART 1000 CCD area detector/Bruker PLATFORM diffractometer | 5524 independent reflections |
Radiation source: fine-focus sealed tube | 4875 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 1.8° |
ω scans | h = −17→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | k = −8→8 |
Tmin = 0.809, Tmax = 0.972 | l = −18→18 |
9410 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0466P)2 + 0.1539P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5524 reflections | Δρmax = 0.22 e Å−3 |
299 parameters | Δρmin = −0.15 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2491 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (6) |
Experimental. Data for (IV): RF 0.49 (5:1 hexanes/EtOAc); [α]D +155.6 (c 0.7, CH2Cl2); 1H NMR (500 MHz, CDCl3) δ 7.42 (d, 2H, J = 8.1 Hz, ArH), 7.13 (d, 2H, J = 8.4 Hz, ArH), 5.25 (d, 1H, J = 5.9 Hz, H-1), 4.31–4.34 (dd, 1H, J = 4.6, 4.6 Hz, H-5), 4.12–4.15 (m, 1H, H-2), 3.98–4.02 (m, 1H, H-3), 3.92–3.96 (m, 1H, H-5'), 3.88–3.91 (m, 1H, H-4), 2.33 (s, 3H, ArCH3), 2.57 (d, 1H, J = 3.2 Hz, OH), 1.06 (s, 9H, C(CH3)3), 0.98 (s, 9H, C(CH3)3); 13C NMR (125 MHz, CDCl3) δ 137.9, 132.3, 130.2, 129.8, 91.4, 81.1, 80.8, 73.8, 67.3, 27.4, 27.1, 22.6, 21.1, 20.1; HRMS (ESI) m/z calculated for C20H32O4SSi + Na: 419.1683, found: 419.1680. Anal. Calcd for C20H32O4SSi: C, 60.57; H, 8.13; S, 8.08. Found: C, 60.09; H, 8.06; S, 7.66. Data for (II): RF 0.77 (5:1 hexanes/EtOAc); [α]D +157.2 (c 0.8, CH2Cl2); 1H NMR (600 MHz, CDCl3): δ 7.41–7.43 (m, 2H, ArH), 7.31–7.39 (m, 5H, ArH), 7.09–7.10 (m, 2H, ArH), 5.36 (d, 1H, J = 5.4 Hz, H-1), 4.80 (ABq, 2H, J = 12.0 Hz, PhCH2), 4.32–4.34 (m, 1H, H-5), 4.13–4.15 (m, 1H, H-3), 3.97–3.98 (m, 1H, H-2), 3.95–3.96 (m, 1H, H-5'), 3.89–3.92 (m, 1H, H-4), 2.33 (s, 3H, ArCH3), 1.08 (s, 9H, C(CH3)3), 0.99 (s, 9H, C(CH3)3); 13C NMR (125 MHz, CDCl3): δ 137.7, 137.6, 132.2, 130.4, 129.7, 128.4, 128.0, 127.8, 90.2, 86.7, 81.3, 73.7, 72.2, 67.3, 27.5, 27.1, 22.6, 21.1, 20.1; HRMS (ESI) m/z calculated for C27H38O4SSi + Na: 509.2153, found: 509.2152. Anal. Calcd for C27H38O4SSi: C, 66.62; H, 7.87; S, 6.59. Found: C, 66.82; H, 7.89; S, 6.10. |
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 | ||
S | 0.36891 (4) | 0.06482 (8) | 0.20166 (3) | 0.03877 (13) | |
Si | 0.26561 (4) | 0.02030 (8) | 0.55574 (3) | 0.03342 (14) | |
O1 | 0.26005 (12) | −0.1946 (2) | 0.28124 (9) | 0.0418 (4) | |
O2 | 0.13419 (10) | 0.2522 (2) | 0.25339 (9) | 0.0379 (3) | |
O3 | 0.24723 (10) | 0.1605 (2) | 0.46066 (8) | 0.0372 (3) | |
O5 | 0.27154 (12) | −0.2237 (2) | 0.52581 (9) | 0.0416 (4) | |
C1 | 0.25530 (14) | −0.0052 (3) | 0.23168 (13) | 0.0354 (4) | |
H1 | 0.2050 | −0.0182 | 0.1748 | 0.043* | |
C2 | 0.22492 (14) | 0.1671 (3) | 0.29213 (12) | 0.0325 (4) | |
H2 | 0.2750 | 0.2779 | 0.3055 | 0.039* | |
C3 | 0.21818 (14) | 0.0479 (3) | 0.37808 (11) | 0.0337 (4) | |
H3 | 0.1507 | −0.0014 | 0.3733 | 0.040* | |
C4 | 0.28243 (16) | −0.1364 (3) | 0.37466 (13) | 0.0371 (5) | |
H4 | 0.3513 | −0.0932 | 0.3921 | 0.044* | |
C5 | 0.26257 (18) | −0.3079 (3) | 0.43687 (13) | 0.0420 (5) | |
H5A | 0.1970 | −0.3633 | 0.4152 | 0.050* | |
H5B | 0.3090 | −0.4224 | 0.4376 | 0.050* | |
C11 | 0.37038 (14) | −0.1079 (3) | 0.11031 (13) | 0.0341 (4) | |
C12 | 0.39664 (16) | −0.0325 (4) | 0.03235 (14) | 0.0419 (5) | |
H12 | 0.4163 | 0.1077 | 0.0299 | 0.050* | |
C13 | 0.39426 (17) | −0.1609 (4) | −0.04155 (15) | 0.0469 (6) | |
H13 | 0.4135 | −0.1078 | −0.0940 | 0.056* | |
C14 | 0.36465 (16) | −0.3646 (4) | −0.04118 (14) | 0.0427 (5) | |
C15 | 0.34135 (15) | −0.4404 (4) | 0.03793 (13) | 0.0426 (5) | |
H15 | 0.3218 | −0.5808 | 0.0401 | 0.051* | |
C16 | 0.34596 (15) | −0.3160 (3) | 0.11362 (14) | 0.0394 (5) | |
H16 | 0.3324 | −0.3728 | 0.1679 | 0.047* | |
C17 | 0.3560 (2) | −0.5004 (5) | −0.12451 (15) | 0.0580 (6) | |
H17A | 0.2892 | −0.5003 | −0.1582 | 0.070* | |
H17B | 0.3753 | −0.6422 | −0.1058 | 0.070* | |
H17C | 0.3978 | −0.4466 | −0.1634 | 0.070* | |
C20 | 0.13761 (15) | 0.3861 (4) | 0.17798 (14) | 0.0398 (5) | |
H20A | 0.1627 | 0.3091 | 0.1309 | 0.048* | |
H20B | 0.1811 | 0.5042 | 0.1984 | 0.048* | |
C21 | 0.03885 (15) | 0.4642 (3) | 0.13937 (13) | 0.0371 (5) | |
C22 | −0.02716 (17) | 0.3405 (4) | 0.08259 (15) | 0.0508 (6) | |
H22 | −0.0092 | 0.2052 | 0.0676 | 0.061* | |
C23 | −0.11866 (19) | 0.4118 (5) | 0.04764 (18) | 0.0641 (8) | |
H23 | −0.1636 | 0.3251 | 0.0093 | 0.077* | |
C24 | −0.1451 (2) | 0.6087 (5) | 0.06832 (19) | 0.0662 (9) | |
H24 | −0.2082 | 0.6572 | 0.0443 | 0.079* | |
C25 | −0.0805 (2) | 0.7352 (5) | 0.1235 (2) | 0.0628 (7) | |
H25 | −0.0986 | 0.8713 | 0.1371 | 0.075* | |
C26 | 0.01122 (18) | 0.6631 (4) | 0.15908 (15) | 0.0479 (5) | |
H26 | 0.0558 | 0.7505 | 0.1974 | 0.058* | |
C31 | 0.15812 (16) | 0.0438 (4) | 0.60958 (14) | 0.0439 (5) | |
C32 | 0.1457 (2) | 0.2666 (4) | 0.64218 (18) | 0.0586 (7) | |
H32A | 0.1466 | 0.3638 | 0.5923 | 0.070* | |
H32B | 0.1983 | 0.2996 | 0.6933 | 0.070* | |
H32C | 0.0843 | 0.2780 | 0.6617 | 0.070* | |
C33 | 0.1613 (2) | −0.1078 (5) | 0.6884 (2) | 0.0667 (8) | |
H33A | 0.2179 | −0.0787 | 0.7361 | 0.080* | |
H33B | 0.1648 | −0.2500 | 0.6666 | 0.080* | |
H33C | 0.1031 | −0.0916 | 0.7131 | 0.080* | |
C34 | 0.06994 (17) | −0.0082 (5) | 0.53469 (18) | 0.0655 (8) | |
H34A | 0.0679 | 0.0852 | 0.4830 | 0.079* | |
H34B | 0.0113 | 0.0089 | 0.5586 | 0.079* | |
H34C | 0.0745 | −0.1519 | 0.5149 | 0.079* | |
C35 | 0.38587 (16) | 0.1021 (4) | 0.62455 (13) | 0.0423 (5) | |
C36 | 0.4030 (2) | 0.0133 (6) | 0.72138 (15) | 0.0683 (8) | |
H36A | 0.3977 | −0.1381 | 0.7185 | 0.082* | |
H36B | 0.3548 | 0.0691 | 0.7531 | 0.082* | |
H36C | 0.4673 | 0.0522 | 0.7544 | 0.082* | |
C37 | 0.3934 (2) | 0.3376 (4) | 0.63143 (19) | 0.0650 (8) | |
H37A | 0.3830 | 0.3974 | 0.5703 | 0.078* | |
H37B | 0.4574 | 0.3762 | 0.6653 | 0.078* | |
H37C | 0.3447 | 0.3906 | 0.6631 | 0.078* | |
C38 | 0.46591 (18) | 0.0228 (6) | 0.57923 (19) | 0.0711 (8) | |
H38A | 0.4577 | 0.0815 | 0.5180 | 0.085* | |
H38B | 0.4629 | −0.1287 | 0.5753 | 0.085* | |
H38C | 0.5284 | 0.0649 | 0.6154 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0387 (3) | 0.0404 (3) | 0.0371 (3) | −0.0045 (2) | 0.0076 (2) | −0.0048 (2) |
Si | 0.0419 (3) | 0.0320 (3) | 0.0263 (2) | 0.0017 (2) | 0.0066 (2) | −0.0008 (2) |
O1 | 0.0664 (10) | 0.0312 (8) | 0.0303 (7) | −0.0070 (7) | 0.0161 (7) | −0.0056 (6) |
O2 | 0.0375 (8) | 0.0456 (8) | 0.0303 (7) | 0.0024 (6) | 0.0062 (6) | 0.0048 (6) |
O3 | 0.0554 (9) | 0.0293 (7) | 0.0251 (6) | 0.0033 (7) | 0.0042 (6) | −0.0025 (6) |
O5 | 0.0638 (10) | 0.0304 (8) | 0.0321 (7) | 0.0033 (7) | 0.0133 (7) | −0.0011 (6) |
C1 | 0.0352 (11) | 0.0395 (12) | 0.0310 (9) | −0.0058 (9) | 0.0054 (8) | −0.0027 (9) |
C2 | 0.0348 (10) | 0.0348 (10) | 0.0270 (9) | −0.0014 (9) | 0.0042 (8) | −0.0031 (8) |
C3 | 0.0409 (10) | 0.0335 (10) | 0.0258 (8) | −0.0029 (9) | 0.0046 (8) | −0.0032 (8) |
C4 | 0.0497 (12) | 0.0326 (11) | 0.0300 (10) | −0.0020 (10) | 0.0108 (9) | −0.0053 (8) |
C5 | 0.0634 (14) | 0.0293 (11) | 0.0341 (10) | 0.0011 (10) | 0.0120 (10) | −0.0043 (9) |
C11 | 0.0323 (10) | 0.0401 (11) | 0.0297 (10) | 0.0017 (9) | 0.0055 (8) | −0.0007 (8) |
C12 | 0.0435 (12) | 0.0412 (12) | 0.0427 (11) | 0.0023 (9) | 0.0122 (10) | 0.0061 (9) |
C13 | 0.0540 (14) | 0.0550 (15) | 0.0347 (11) | 0.0066 (11) | 0.0161 (10) | 0.0069 (10) |
C14 | 0.0425 (12) | 0.0500 (13) | 0.0349 (11) | 0.0066 (10) | 0.0065 (9) | −0.0017 (9) |
C15 | 0.0462 (12) | 0.0392 (12) | 0.0433 (11) | 0.0001 (10) | 0.0115 (9) | −0.0033 (10) |
C16 | 0.0441 (12) | 0.0383 (12) | 0.0375 (11) | −0.0009 (10) | 0.0126 (9) | 0.0038 (9) |
C17 | 0.0654 (16) | 0.0670 (17) | 0.0410 (12) | 0.0011 (14) | 0.0100 (11) | −0.0094 (12) |
C20 | 0.0373 (11) | 0.0477 (13) | 0.0337 (11) | −0.0015 (10) | 0.0054 (9) | 0.0082 (9) |
C21 | 0.0385 (11) | 0.0436 (12) | 0.0284 (10) | −0.0022 (9) | 0.0051 (8) | 0.0066 (9) |
C22 | 0.0524 (14) | 0.0547 (15) | 0.0415 (12) | −0.0070 (12) | 0.0012 (11) | −0.0002 (11) |
C23 | 0.0474 (15) | 0.088 (2) | 0.0506 (15) | −0.0161 (15) | −0.0046 (12) | 0.0109 (15) |
C24 | 0.0396 (14) | 0.091 (2) | 0.0648 (17) | 0.0095 (14) | 0.0037 (12) | 0.0301 (16) |
C25 | 0.0624 (17) | 0.0560 (16) | 0.0755 (18) | 0.0132 (14) | 0.0269 (15) | 0.0188 (14) |
C26 | 0.0501 (14) | 0.0486 (13) | 0.0461 (12) | −0.0011 (11) | 0.0123 (10) | 0.0057 (11) |
C31 | 0.0491 (12) | 0.0439 (12) | 0.0415 (11) | 0.0009 (12) | 0.0155 (9) | −0.0068 (10) |
C32 | 0.0675 (17) | 0.0545 (16) | 0.0567 (15) | 0.0118 (13) | 0.0194 (13) | −0.0100 (13) |
C33 | 0.0768 (19) | 0.0608 (17) | 0.0741 (19) | 0.0030 (15) | 0.0425 (16) | 0.0088 (14) |
C34 | 0.0433 (14) | 0.083 (2) | 0.0732 (17) | −0.0029 (14) | 0.0194 (12) | −0.0190 (16) |
C35 | 0.0455 (12) | 0.0491 (14) | 0.0301 (10) | −0.0015 (10) | 0.0029 (9) | 0.0044 (9) |
C36 | 0.0670 (17) | 0.088 (2) | 0.0401 (12) | −0.0082 (17) | −0.0109 (11) | 0.0193 (15) |
C37 | 0.0670 (18) | 0.0556 (17) | 0.0625 (16) | −0.0130 (14) | −0.0094 (13) | −0.0063 (13) |
C38 | 0.0434 (14) | 0.099 (2) | 0.0711 (16) | −0.0058 (16) | 0.0128 (12) | −0.0128 (18) |
S—C1 | 1.822 (2) | C20—H20A | 0.99 |
S—C11 | 1.773 (2) | C20—H20B | 0.99 |
Si—O3 | 1.6668 (14) | C21—C22 | 1.385 (3) |
Si—O5 | 1.6447 (15) | C21—C26 | 1.392 (3) |
Si—C31 | 1.878 (2) | C22—C23 | 1.379 (4) |
Si—C35 | 1.884 (2) | C22—H22 | 0.95 |
O1—C1 | 1.426 (2) | C23—C24 | 1.379 (4) |
O1—C4 | 1.426 (2) | C23—H23 | 0.95 |
O2—C2 | 1.413 (2) | C24—C25 | 1.373 (4) |
O2—C20 | 1.435 (2) | C24—H24 | 0.95 |
O3—C3 | 1.425 (2) | C25—C26 | 1.385 (4) |
O5—C5 | 1.425 (2) | C25—H25 | 0.95 |
C1—C2 | 1.553 (3) | C26—H26 | 0.95 |
C1—H1 | 1.00 | C31—C32 | 1.541 (3) |
C2—C3 | 1.524 (3) | C31—C33 | 1.531 (3) |
C2—H2 | 1.00 | C31—C34 | 1.541 (3) |
C3—C4 | 1.507 (3) | C32—H32A | 0.98 |
C3—H3 | 1.00 | C32—H32B | 0.98 |
C4—C5 | 1.513 (3) | C32—H32C | 0.98 |
C4—H4 | 1.00 | C33—H33A | 0.98 |
C5—H5A | 0.99 | C33—H33B | 0.98 |
C5—H5B | 0.99 | C33—H33C | 0.98 |
C11—C12 | 1.390 (3) | C34—H34A | 0.98 |
C11—C16 | 1.391 (3) | C34—H34B | 0.98 |
C12—C13 | 1.381 (3) | C34—H34C | 0.98 |
C12—H12 | 0.95 | C35—C36 | 1.537 (3) |
C13—C14 | 1.380 (3) | C35—C37 | 1.526 (3) |
C13—H13 | 0.95 | C35—C38 | 1.530 (4) |
C14—C15 | 1.388 (3) | C36—H36A | 0.98 |
C14—C17 | 1.514 (3) | C36—H36B | 0.98 |
C15—C16 | 1.384 (3) | C36—H36C | 0.98 |
C15—H15 | 0.95 | C37—H37A | 0.98 |
C16—H16 | 0.95 | C37—H37B | 0.98 |
C17—H17A | 0.98 | C37—H37C | 0.98 |
C17—H17B | 0.98 | C38—H38A | 0.98 |
C17—H17C | 0.98 | C38—H38B | 0.98 |
C20—C21 | 1.493 (3) | C38—H38C | 0.98 |
C1—S—C11 | 100.87 (9) | C21—C20—H20B | 109.8 |
O3—Si—O5 | 107.01 (7) | H20A—C20—H20B | 108.3 |
O3—Si—C31 | 109.16 (9) | C20—C21—C22 | 120.7 (2) |
O3—Si—C35 | 106.50 (9) | C20—C21—C26 | 120.8 (2) |
O5—Si—C31 | 106.70 (10) | C22—C21—C26 | 118.5 (2) |
O5—Si—C35 | 109.08 (9) | C21—C22—C23 | 120.7 (3) |
C31—Si—C35 | 117.93 (10) | C21—C22—H22 | 119.6 |
C1—O1—C4 | 105.45 (14) | C23—C22—H22 | 119.6 |
C2—O2—C20 | 112.54 (14) | C22—C23—C24 | 120.0 (3) |
Si—O3—C3 | 115.95 (12) | C22—C23—H23 | 120.0 |
Si—O5—C5 | 128.46 (13) | C24—C23—H23 | 120.0 |
S—C1—O1 | 113.14 (14) | C23—C24—C25 | 120.3 (3) |
S—C1—C2 | 109.59 (14) | C23—C24—H24 | 119.8 |
S—C1—H1 | 108.9 | C25—C24—H24 | 119.8 |
O1—C1—C2 | 107.25 (15) | C24—C25—C26 | 119.6 (3) |
O1—C1—H1 | 108.9 | C24—C25—H25 | 120.2 |
C2—C1—H1 | 108.9 | C26—C25—H25 | 120.2 |
O2—C2—C1 | 112.16 (15) | C21—C26—C25 | 120.8 (2) |
O2—C2—C3 | 109.53 (16) | C21—C26—H26 | 119.6 |
O2—C2—H2 | 110.9 | C25—C26—H26 | 119.6 |
C1—C2—C3 | 102.06 (16) | Si—C31—C32 | 111.68 (17) |
C1—C2—H2 | 110.9 | Si—C31—C33 | 112.71 (17) |
C3—C2—H2 | 110.9 | Si—C31—C34 | 106.25 (14) |
O3—C3—C2 | 115.13 (16) | C32—C31—C33 | 109.7 (2) |
O3—C3—C4 | 111.27 (16) | C32—C31—C34 | 107.8 (2) |
O3—C3—H3 | 109.1 | C33—C31—C34 | 108.5 (2) |
C2—C3—C4 | 103.00 (15) | C31—C32—H32A | 109.5 |
C2—C3—H3 | 109.1 | C31—C32—H32B | 109.5 |
C4—C3—H3 | 109.1 | C31—C32—H32C | 109.5 |
O1—C4—C3 | 103.14 (16) | H32A—C32—H32B | 109.5 |
O1—C4—C5 | 112.62 (17) | H32A—C32—H32C | 109.5 |
O1—C4—H4 | 109.8 | H32B—C32—H32C | 109.5 |
C3—C4—C5 | 111.37 (17) | C31—C33—H33A | 109.5 |
C3—C4—H4 | 109.8 | C31—C33—H33B | 109.5 |
C5—C4—H4 | 109.8 | C31—C33—H33C | 109.5 |
O5—C5—C4 | 108.06 (16) | H33A—C33—H33B | 109.5 |
O5—C5—H5A | 110.1 | H33A—C33—H33C | 109.5 |
O5—C5—H5B | 110.1 | H33B—C33—H33C | 109.5 |
C4—C5—H5A | 110.1 | C31—C34—H34A | 109.5 |
C4—C5—H5B | 110.1 | C31—C34—H34B | 109.5 |
H5A—C5—H5B | 108.4 | C31—C34—H34C | 109.5 |
S—C11—C12 | 118.83 (17) | H34A—C34—H34B | 109.5 |
S—C11—C16 | 122.45 (16) | H34A—C34—H34C | 109.5 |
C12—C11—C16 | 118.7 (2) | H34B—C34—H34C | 109.5 |
C11—C12—C13 | 120.2 (2) | Si—C35—C36 | 111.41 (17) |
C11—C12—H12 | 119.9 | Si—C35—C37 | 111.09 (17) |
C13—C12—H12 | 119.9 | Si—C35—C38 | 109.65 (16) |
C12—C13—C14 | 121.7 (2) | C36—C35—C37 | 108.2 (2) |
C12—C13—H13 | 119.2 | C36—C35—C38 | 108.1 (2) |
C14—C13—H13 | 119.2 | C37—C35—C38 | 108.4 (2) |
C13—C14—C15 | 117.8 (2) | C35—C36—H36A | 109.5 |
C13—C14—C17 | 121.4 (2) | C35—C36—H36B | 109.5 |
C15—C14—C17 | 120.8 (2) | C35—C36—H36C | 109.5 |
C14—C15—C16 | 121.4 (2) | H36A—C36—H36B | 109.5 |
C14—C15—H15 | 119.3 | H36A—C36—H36C | 109.5 |
C16—C15—H15 | 119.3 | H36B—C36—H36C | 109.5 |
C11—C16—C15 | 120.0 (2) | C35—C37—H37A | 109.5 |
C11—C16—H16 | 120.0 | C35—C37—H37B | 109.5 |
C15—C16—H16 | 120.0 | C35—C37—H37C | 109.5 |
C14—C17—H17A | 109.5 | H37A—C37—H37B | 109.5 |
C14—C17—H17B | 109.5 | H37A—C37—H37C | 109.5 |
C14—C17—H17C | 109.5 | H37B—C37—H37C | 109.5 |
H17A—C17—H17B | 109.5 | C35—C38—H38A | 109.5 |
H17A—C17—H17C | 109.5 | C35—C38—H38B | 109.5 |
H17B—C17—H17C | 109.5 | C35—C38—H38C | 109.5 |
O2—C20—C21 | 109.18 (16) | H38A—C38—H38B | 109.5 |
O2—C20—H20A | 109.8 | H38A—C38—H38C | 109.5 |
O2—C20—H20B | 109.8 | H38B—C38—H38C | 109.5 |
C21—C20—H20A | 109.8 | ||
C11—S—C1—O1 | 76.26 (14) | Si—O3—C3—C4 | −49.24 (19) |
C11—S—C1—C2 | −164.11 (13) | Si—O5—C5—C4 | 20.5 (3) |
C1—S—C11—C12 | 135.25 (17) | O1—C1—C2—O2 | −115.28 (17) |
C1—S—C11—C16 | −44.6 (2) | O1—C1—C2—C3 | 1.9 (2) |
O5—Si—O3—C3 | 14.43 (15) | S—C1—C2—O2 | 121.54 (15) |
C31—Si—O3—C3 | −100.69 (15) | S—C1—C2—C3 | −121.32 (14) |
C35—Si—O3—C3 | 130.98 (14) | O2—C2—C3—O3 | −96.46 (19) |
O3—Si—O5—C5 | −0.4 (2) | O2—C2—C3—C4 | 142.24 (17) |
C31—Si—O5—C5 | 116.38 (19) | C1—C2—C3—O3 | 144.52 (16) |
C35—Si—O5—C5 | −115.22 (18) | C1—C2—C3—C4 | 23.23 (19) |
O3—Si—C31—C32 | −65.60 (17) | O3—C3—C4—O1 | −165.09 (15) |
O3—Si—C31—C33 | 170.42 (17) | O3—C3—C4—C5 | 73.9 (2) |
O3—Si—C31—C34 | 51.7 (2) | C2—C3—C4—O1 | −41.20 (19) |
O5—Si—C31—C32 | 179.08 (16) | C2—C3—C4—C5 | −162.24 (16) |
O5—Si—C31—C33 | 55.10 (19) | O1—C4—C5—O5 | −170.33 (17) |
O5—Si—C31—C34 | −63.6 (2) | C3—C4—C5—O5 | −55.0 (2) |
C35—Si—C31—C32 | 56.03 (19) | S—C11—C12—C13 | −177.05 (17) |
C35—Si—C31—C33 | −67.9 (2) | C16—C11—C12—C13 | 2.8 (3) |
C35—Si—C31—C34 | 173.38 (18) | S—C11—C16—C15 | 175.15 (16) |
O3—Si—C35—C36 | 169.58 (18) | C12—C11—C16—C15 | −4.7 (3) |
O3—Si—C35—C37 | 48.90 (19) | C11—C12—C13—C14 | 1.1 (3) |
O3—Si—C35—C38 | −70.8 (2) | C12—C13—C14—C15 | −3.0 (3) |
O5—Si—C35—C36 | −75.3 (2) | C12—C13—C14—C17 | 175.9 (2) |
O5—Si—C35—C37 | 164.06 (17) | C13—C14—C15—C16 | 1.0 (3) |
O5—Si—C35—C38 | 44.3 (2) | C17—C14—C15—C16 | −177.9 (2) |
C31—Si—C35—C36 | 46.6 (2) | C14—C15—C16—C11 | 2.8 (3) |
C31—Si—C35—C37 | −74.1 (2) | O2—C20—C21—C22 | −78.9 (2) |
C31—Si—C35—C38 | 166.17 (19) | O2—C20—C21—C26 | 101.5 (2) |
C4—O1—C1—S | 92.88 (16) | C20—C21—C22—C23 | 179.4 (2) |
C4—O1—C1—C2 | −28.1 (2) | C26—C21—C22—C23 | −1.1 (3) |
C1—O1—C4—C3 | 43.31 (19) | C20—C21—C26—C25 | −179.8 (2) |
C1—O1—C4—C5 | 163.49 (18) | C22—C21—C26—C25 | 0.6 (3) |
C20—O2—C2—C1 | −74.1 (2) | C21—C22—C23—C24 | 0.7 (4) |
C20—O2—C2—C3 | 173.37 (16) | C22—C23—C24—C25 | 0.2 (4) |
C2—O2—C20—C21 | 178.32 (17) | C23—C24—C25—C26 | −0.6 (4) |
Si—O3—C3—C2 | −165.94 (13) | C24—C25—C26—C21 | 0.2 (4) |