Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000336X/qa0240sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010000336X/qa0240Isup2.hkl |
CCDC reference: 144699
The title optically active compound was prepared by the authors in a synthetic study on bryostatins (Ohmori et al., 2000). The angle of rotation [α]D22 is -6.24 ° (c 1.0, CHCl3). Crystals were grown from a hexane/ethyl acetate solution.
Hydroxyl H atoms were located from a difference synthesis and their positional parameters were refined with restraint of O—H = 0.98 Å (s.u. 0.01 Å) with Uiso(H) = 1.2Ueq(parent atom). The other H-atom positional parameters were calculated geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom). A residual density of 1.00 e Å-3 was located at 1.11 Å from the C88 atom, suggesting an orientational disorder of the tetramethylsilapropoxy group. The absolute structure was determined based on Flack parameter of 0.0 (1), which is consistent with the expected absolute configuration of 3S produced by Sharpless asymmetric epoxidation protcol. The two independent molecules are related approximately by a translation of (0.47, -0.05, 1/2), except for the methoxy O atoms.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.
C32H56O6S2Si | Dx = 1.167 Mg m−3 |
Mr = 629.00 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21 | Cell parameters from 25 reflections |
a = 6.878 (3) Å | θ = 14.3–15.0° |
b = 19.658 (3) Å | µ = 0.22 mm−1 |
c = 26.493 (2) Å | T = 298 K |
β = 91.33 (2)° | Plate-like, colourless |
V = 3581.1 (17) Å3 | 0.7 × 0.6 × 0.1 mm |
Z = 4 |
Rigaku AFC5 diffractometer | Rint = 0.030 |
ω scans | θmax = 25°, θmin = 2.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→8 |
Tmin = 0.881, Tmax = 0.977 | k = 0→23 |
7078 measured reflections | l = −31→31 |
6497 independent reflections | 3 standard reflections every 100 reflections |
4622 reflections with I > 2σ(I) | intensity decay: 1.0% |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0591P)2 + 1.2827P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.051 | (Δ/σ)max = 0.017 |
wR(F2) = 0.130 | Δρmax = 1.00 e Å−3 |
S = 1.02 | Δρmin = −0.29 e Å−3 |
6497 reflections | Absolute structure: Flack (1983), no Friedel pairs |
745 parameters | Absolute structure parameter: 0.0 (1) |
H atoms treated by a mixture of independent and constrained refinement |
C32H56O6S2Si | V = 3581.1 (17) Å3 |
Mr = 629.00 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.878 (3) Å | µ = 0.22 mm−1 |
b = 19.658 (3) Å | T = 298 K |
c = 26.493 (2) Å | 0.7 × 0.6 × 0.1 mm |
β = 91.33 (2)° |
Rigaku AFC5 diffractometer | 4622 reflections with I > 2σ(I) |
Absorption correction: integration (Coppens et al., 1965) | Rint = 0.030 |
Tmin = 0.881, Tmax = 0.977 | 3 standard reflections every 100 reflections |
7078 measured reflections | intensity decay: 1.0% |
6497 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | Δρmax = 1.00 e Å−3 |
S = 1.02 | Δρmin = −0.29 e Å−3 |
6497 reflections | Absolute structure: Flack (1983), no Friedel pairs |
745 parameters | Absolute structure parameter: 0.0 (1) |
Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt). |
x | y | z | Uiso*/Ueq | ||
S1 | −0.2505 (2) | 0.70209 (9) | 0.94213 (6) | 0.0492 (4) | |
S2 | 0.1644 (2) | 0.73805 (7) | 0.91772 (6) | 0.0447 (4) | |
S51 | −0.7194 (2) | 0.74784 (8) | 0.43871 (6) | 0.0442 (4) | |
S52 | −0.3093 (2) | 0.78914 (7) | 0.41375 (6) | 0.0433 (4) | |
Si3 | −0.1647 (3) | 0.7039 (1) | 1.13615 (7) | 0.0542 (5) | |
Si53 | −0.6388 (3) | 0.7629 (1) | 0.63296 (7) | 0.0615 (5) | |
O4 | 0.2922 (5) | 0.5363 (2) | 0.9461 (1) | 0.0413 (9) | |
O5 | 0.5343 (7) | 0.5533 (2) | 0.8298 (2) | 0.066 (1) | |
O6 | 0.3625 (8) | 0.4556 (2) | 0.8056 (2) | 0.069 (1) | |
O7 | 0.4612 (7) | 0.4198 (2) | 0.9916 (2) | 0.059 (1) | |
O8 | −0.0036 (6) | 0.7133 (2) | 1.0916 (1) | 0.048 (1) | |
O9 | −0.0102 (7) | 0.9197 (2) | 1.0391 (2) | 0.059 (1) | |
O54 | −0.1691 (5) | 0.5891 (2) | 0.4547 (1) | 0.0391 (9) | |
O55 | 0.0802 (6) | 0.5872 (2) | 0.3370 (1) | 0.046 (1) | |
O56 | −0.0697 (7) | 0.4819 (2) | 0.3261 (2) | 0.052 (1) | |
O57 | −0.0464 (8) | 0.4773 (2) | 0.5110 (2) | 0.066 (1) | |
O58 | −0.4779 (7) | 0.7729 (2) | 0.5877 (1) | 0.053 (1) | |
O59 | −0.5285 (7) | 0.9752 (2) | 0.5284 (2) | 0.067 (1) | |
C10 | −0.287 (1) | 0.7162 (4) | 0.8753 (3) | 0.069 (2) | |
C11 | −0.153 (1) | 0.7670 (4) | 0.8525 (3) | 0.072 (2) | |
C12 | 0.062 (1) | 0.7445 (4) | 0.8545 (2) | 0.064 (2) | |
C13 | 0.0076 (7) | 0.6744 (3) | 0.9477 (2) | 0.036 (1) | |
C14 | 0.0203 (8) | 0.6059 (3) | 0.9179 (2) | 0.041 (1) | |
C15 | 0.2179 (8) | 0.5767 (3) | 0.9045 (2) | 0.042 (1) | |
C16 | 0.204 (1) | 0.5312 (3) | 0.8582 (2) | 0.054 (2) | |
C17 | 0.401 (1) | 0.5019 (3) | 0.8458 (2) | 0.054 (2) | |
C18 | 0.4975 (10) | 0.4694 (3) | 0.8912 (2) | 0.050 (2) | |
C19 | 0.4871 (8) | 0.5158 (3) | 0.9380 (2) | 0.043 (1) | |
C20 | 0.5616 (9) | 0.4822 (3) | 0.9857 (3) | 0.049 (2) | |
C21 | 0.521 (1) | 0.3838 (4) | 1.0358 (3) | 0.072 (2) | |
C22 | 0.446 (1) | 0.4143 (3) | 1.0836 (3) | 0.061 (2) | |
C23 | 0.263 (1) | 0.4403 (5) | 1.0856 (3) | 0.086 (3) | |
C24 | 0.194 (2) | 0.4653 (6) | 1.1302 (5) | 0.124 (4) | |
C25 | 0.304 (3) | 0.4659 (7) | 1.1724 (5) | 0.149 (7) | |
C26 | 0.484 (3) | 0.4377 (7) | 1.1719 (4) | 0.134 (5) | |
C27 | 0.559 (2) | 0.4127 (5) | 1.1271 (4) | 0.095 (3) | |
C28 | 0.471 (1) | 0.5932 (4) | 0.7879 (3) | 0.089 (3) | |
C29 | 0.528 (1) | 0.4199 (5) | 0.7878 (3) | 0.091 (3) | |
C30 | 0.0604 (8) | 0.6700 (3) | 1.0065 (2) | 0.039 (1) | |
C31 | −0.017 (1) | 0.6017 (3) | 1.0264 (2) | 0.052 (2) | |
C32 | 0.2819 (9) | 0.6702 (3) | 1.0165 (2) | 0.049 (2) | |
C33 | −0.0362 (8) | 0.7282 (3) | 1.0386 (2) | 0.041 (1) | |
C34 | 0.0394 (9) | 0.7998 (3) | 1.0283 (2) | 0.047 (2) | |
C35 | −0.0735 (10) | 0.8540 (3) | 1.0550 (2) | 0.054 (2) | |
C36 | −0.376 (1) | 0.7621 (4) | 1.1295 (3) | 0.075 (2) | |
C37 | −0.269 (2) | 0.6166 (5) | 1.1387 (4) | 0.112 (4) | |
C38 | −0.022 (1) | 0.7215 (5) | 1.1960 (3) | 0.082 (3) | |
C39 | 0.148 (2) | 0.6724 (7) | 1.2020 (4) | 0.134 (5) | |
C40 | 0.060 (2) | 0.7939 (6) | 1.1948 (4) | 0.117 (4) | |
C41 | −0.155 (2) | 0.7137 (7) | 1.2423 (3) | 0.133 (5) | |
C60 | −0.7599 (9) | 0.7573 (4) | 0.3714 (3) | 0.056 (2) | |
C61 | −0.627 (1) | 0.8092 (4) | 0.3474 (3) | 0.068 (2) | |
C62 | −0.417 (1) | 0.7898 (4) | 0.3500 (2) | 0.060 (2) | |
C63 | −0.4573 (7) | 0.7257 (3) | 0.4462 (2) | 0.034 (1) | |
C64 | −0.4332 (8) | 0.6557 (3) | 0.4189 (2) | 0.038 (1) | |
C65 | −0.2304 (8) | 0.6256 (3) | 0.4109 (2) | 0.035 (1) | |
C66 | −0.2360 (8) | 0.5764 (3) | 0.3655 (2) | 0.041 (1) | |
C67 | −0.0466 (9) | 0.5388 (3) | 0.3584 (2) | 0.042 (1) | |
C68 | 0.0290 (9) | 0.5105 (3) | 0.4082 (2) | 0.043 (1) | |
C69 | 0.0239 (8) | 0.5625 (3) | 0.4511 (2) | 0.037 (1) | |
C70 | 0.0788 (9) | 0.5330 (3) | 0.5014 (2) | 0.047 (2) | |
C71 | 0.011 (1) | 0.4363 (4) | 0.5527 (3) | 0.077 (2) | |
C72 | −0.028 (1) | 0.4683 (4) | 0.6036 (3) | 0.070 (2) | |
C73 | −0.198 (2) | 0.4999 (6) | 0.6120 (4) | 0.109 (3) | |
C74 | −0.238 (2) | 0.5257 (7) | 0.6588 (6) | 0.144 (5) | |
C75 | −0.107 (3) | 0.5189 (8) | 0.6967 (5) | 0.147 (6) | |
C76 | 0.064 (3) | 0.4878 (8) | 0.6908 (4) | 0.146 (6) | |
C77 | 0.105 (2) | 0.4627 (6) | 0.6425 (4) | 0.113 (4) | |
C78 | 0.2619 (9) | 0.5619 (4) | 0.3221 (3) | 0.063 (2) | |
C79 | −0.150 (1) | 0.4942 (4) | 0.2772 (3) | 0.068 (2) | |
C80 | −0.4074 (8) | 0.7252 (3) | 0.5054 (2) | 0.038 (1) | |
C81 | −0.4774 (10) | 0.6572 (3) | 0.5273 (2) | 0.048 (2) | |
C82 | −0.1896 (9) | 0.7310 (3) | 0.5150 (2) | 0.049 (1) | |
C83 | −0.5125 (8) | 0.7839 (3) | 0.5345 (2) | 0.041 (1) | |
C84 | −0.4531 (9) | 0.8566 (3) | 0.5214 (2) | 0.045 (1) | |
C85 | −0.580 (1) | 0.9090 (3) | 0.5449 (3) | 0.059 (2) | |
C86 | −0.856 (1) | 0.8177 (4) | 0.6278 (3) | 0.072 (2) | |
C87 | −0.739 (2) | 0.6757 (4) | 0.6376 (4) | 0.099 (3) | |
C88 | −0.489 (1) | 0.7836 (5) | 0.6911 (3) | 0.081 (2) | |
C89 | −0.320 (1) | 0.7322 (6) | 0.6957 (3) | 0.105 (3) | |
C90 | −0.406 (1) | 0.8575 (5) | 0.6857 (3) | 0.093 (3) | |
C91 | −0.624 (2) | 0.7802 (7) | 0.7382 (3) | 0.127 (4) | |
H9 | −0.131 (6) | 0.945 (3) | 1.035 (2) | 0.0732* | |
H10A | −0.2708 | 0.6739 | 0.8580 | 0.0826* | |
H10B | −0.4189 | 0.7322 | 0.8693 | 0.0826* | |
H11A | −0.1899 | 0.7762 | 0.8183 | 0.0852* | |
H11B | −0.1596 | 0.8096 | 0.8716 | 0.0852* | |
H12A | 0.1377 | 0.7770 | 0.8353 | 0.0741* | |
H12B | 0.0701 | 0.7010 | 0.8382 | 0.0741* | |
H14A | −0.0471 | 0.5729 | 0.9372 | 0.0514* | |
H14B | −0.0513 | 0.6134 | 0.8862 | 0.0514* | |
H15 | 0.3087 | 0.6140 | 0.8984 | 0.0500* | |
H16A | 0.1114 | 0.4956 | 0.8634 | 0.0673* | |
H16B | 0.1551 | 0.5586 | 0.8292 | 0.0673* | |
H18A | 0.4319 | 0.4272 | 0.8986 | 0.0598* | |
H18B | 0.6312 | 0.4598 | 0.8843 | 0.0598* | |
H19 | 0.5645 | 0.5563 | 0.9318 | 0.0535* | |
H20A | 0.5379 | 0.5123 | 1.0142 | 0.0599* | |
H20B | 0.6989 | 0.4749 | 0.9838 | 0.0599* | |
H21A | 0.4720 | 0.3379 | 1.0333 | 0.0852* | |
H21B | 0.6603 | 0.3827 | 1.0376 | 0.0852* | |
H23 | 0.1822 | 0.4402 | 1.0542 | 0.1051* | |
H24 | 0.0527 | 0.4823 | 1.1299 | 0.1629* | |
H25 | 0.2445 | 0.4852 | 1.2038 | 0.1735* | |
H26 | 0.5709 | 0.4399 | 1.2014 | 0.1572* | |
H27 | 0.6909 | 0.3934 | 1.1255 | 0.1111* | |
H28A | 0.5717 | 0.6266 | 0.7805 | 0.1034* | |
H28B | 0.4528 | 0.5644 | 0.7592 | 0.1034* | |
H28C | 0.3541 | 0.6166 | 0.7953 | 0.1034* | |
H29A | 0.5928 | 0.3943 | 0.8146 | 0.1028* | |
H29B | 0.4923 | 0.3899 | 0.7609 | 0.1028* | |
H29C | 0.6240 | 0.4525 | 0.7751 | 0.1028* | |
H31A | −0.1546 | 0.5986 | 1.0209 | 0.0649* | |
H31B | 0.0463 | 0.5649 | 1.0096 | 0.0649* | |
H31C | 0.0120 | 0.5987 | 1.0623 | 0.0649* | |
H32A | 0.3077 | 0.6669 | 1.0530 | 0.0598* | |
H32B | 0.3423 | 0.6333 | 1.0003 | 0.0598* | |
H32C | 0.3379 | 0.7127 | 1.0053 | 0.0598* | |
H33 | −0.1767 | 0.7279 | 1.0315 | 0.0483* | |
H34A | 0.1749 | 0.8028 | 1.0395 | 0.0596* | |
H34B | 0.0325 | 0.8087 | 0.9926 | 0.0596* | |
H35A | −0.0530 | 0.8501 | 1.0913 | 0.0628* | |
H35B | −0.2104 | 0.8490 | 1.0476 | 0.0628* | |
H36A | −0.3331 | 0.8086 | 1.1303 | 0.0934* | |
H36B | −0.4426 | 0.7537 | 1.0975 | 0.0934* | |
H36C | −0.4645 | 0.7543 | 1.1563 | 0.0934* | |
H37A | −0.3620 | 0.6121 | 1.1649 | 0.1440* | |
H37B | −0.3325 | 0.6044 | 1.1067 | 0.1440* | |
H37C | −0.1662 | 0.5829 | 1.1449 | 0.1440* | |
H39A | 0.1010 | 0.6263 | 1.2046 | 0.1606* | |
H39B | 0.2356 | 0.6760 | 1.1751 | 0.1606* | |
H39C | 0.2201 | 0.6823 | 1.2338 | 0.1606* | |
H40A | 0.1270 | 0.8064 | 1.2257 | 0.1337* | |
H40B | 0.1465 | 0.8010 | 1.1670 | 0.1337* | |
H40C | −0.0464 | 0.8285 | 1.1899 | 0.1337* | |
H41A | −0.0769 | 0.7217 | 1.2734 | 0.1608* | |
H41B | −0.2623 | 0.7424 | 1.2415 | 0.1608* | |
H41C | −0.1977 | 0.6660 | 1.2443 | 0.1608* | |
H59 | −0.646 (6) | 1.000 (3) | 0.518 (3) | 0.0822* | |
H60A | −0.7383 | 0.7146 | 0.3559 | 0.0694* | |
H60B | −0.8923 | 0.7705 | 0.3656 | 0.0694* | |
H61A | −0.6663 | 0.8169 | 0.3134 | 0.0808* | |
H61B | −0.6416 | 0.8525 | 0.3654 | 0.0808* | |
H62A | −0.3450 | 0.8217 | 0.3302 | 0.0721* | |
H62B | −0.4048 | 0.7461 | 0.3361 | 0.0721* | |
H64A | −0.5043 | 0.6231 | 0.4380 | 0.0496* | |
H64B | −0.4947 | 0.6603 | 0.3857 | 0.0496* | |
H65 | −0.1381 | 0.6623 | 0.4049 | 0.0427* | |
H66A | −0.3407 | 0.5447 | 0.3703 | 0.0501* | |
H66B | −0.2688 | 0.6032 | 0.3351 | 0.0501* | |
H68A | −0.0523 | 0.4729 | 0.4178 | 0.0515* | |
H68B | 0.1595 | 0.4952 | 0.4046 | 0.0515* | |
H69 | 0.1116 | 0.6009 | 0.4431 | 0.0479* | |
H70A | 0.0672 | 0.5671 | 0.5280 | 0.0557* | |
H70B | 0.2122 | 0.5177 | 0.5017 | 0.0557* | |
H71A | −0.0556 | 0.3937 | 0.5508 | 0.0948* | |
H71B | 0.1499 | 0.4283 | 0.5510 | 0.0948* | |
H73 | −0.2880 | 0.5052 | 0.5828 | 0.1351* | |
H74 | −0.3737 | 0.5485 | 0.6625 | 0.1798* | |
H75 | −0.1367 | 0.5365 | 0.7316 | 0.1921* | |
H76 | 0.1688 | 0.4860 | 0.7172 | 0.1970* | |
H77 | 0.2210 | 0.4373 | 0.6366 | 0.1390* | |
H78A | 0.3336 | 0.5430 | 0.3512 | 0.0811* | |
H78B | 0.2474 | 0.5270 | 0.2971 | 0.0811* | |
H78C | 0.3417 | 0.5982 | 0.3085 | 0.0811* | |
H79A | −0.2816 | 0.5140 | 0.2790 | 0.0805* | |
H79B | −0.0732 | 0.5260 | 0.2581 | 0.0805* | |
H79C | −0.1624 | 0.4527 | 0.2580 | 0.0805* | |
H81A | −0.6148 | 0.6525 | 0.5213 | 0.0587* | |
H81B | −0.4104 | 0.6207 | 0.5112 | 0.0587* | |
H81C | −0.4492 | 0.6565 | 0.5629 | 0.0587* | |
H82A | −0.1596 | 0.7296 | 0.5508 | 0.0588* | |
H82B | −0.1224 | 0.6941 | 0.4989 | 0.0588* | |
H82C | −0.1388 | 0.7735 | 0.5019 | 0.0588* | |
H83 | −0.6528 | 0.7794 | 0.5278 | 0.0498* | |
H84A | −0.3219 | 0.8645 | 0.5319 | 0.0566* | |
H84B | −0.4617 | 0.8627 | 0.4844 | 0.0566* | |
H85A | −0.5665 | 0.9065 | 0.5805 | 0.0754* | |
H85B | −0.7152 | 0.9002 | 0.5350 | 0.0754* | |
H86A | −0.8143 | 0.8654 | 0.6297 | 0.0853* | |
H86B | −0.9225 | 0.8102 | 0.5968 | 0.0853* | |
H86C | −0.9383 | 0.8090 | 0.6558 | 0.0853* | |
H87A | −0.8251 | 0.6710 | 0.6637 | 0.1269* | |
H87B | −0.7968 | 0.6618 | 0.6055 | 0.1269* | |
H87C | −0.6272 | 0.6435 | 0.6437 | 0.1269* | |
H89A | −0.3643 | 0.6879 | 0.7003 | 0.1250* | |
H89B | −0.2366 | 0.7357 | 0.6672 | 0.1250* | |
H89C | −0.2362 | 0.7447 | 0.7260 | 0.1250* | |
H90A | −0.3214 | 0.8697 | 0.7147 | 0.1126* | |
H90B | −0.3235 | 0.8607 | 0.6559 | 0.1126* | |
H90C | −0.5046 | 0.8918 | 0.6825 | 0.1126* | |
H91A | −0.5568 | 0.7888 | 0.7678 | 0.1611* | |
H91B | −0.7327 | 0.8114 | 0.7331 | 0.1611* | |
H91C | −0.6807 | 0.7340 | 0.7385 | 0.1611* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0401 (8) | 0.0544 (10) | 0.0532 (10) | 0.0073 (8) | 0.0036 (7) | −0.0045 (8) |
S2 | 0.0538 (9) | 0.0369 (8) | 0.0439 (9) | −0.0065 (7) | 0.0119 (7) | −0.0032 (7) |
S51 | 0.0357 (7) | 0.0413 (9) | 0.0559 (9) | 0.0062 (7) | 0.0074 (7) | 0.0000 (7) |
S52 | 0.0503 (9) | 0.0365 (8) | 0.0437 (8) | −0.0088 (7) | 0.0125 (7) | −0.0030 (7) |
Si3 | 0.063 (1) | 0.049 (1) | 0.051 (1) | −0.0004 (9) | 0.0183 (9) | 0.0017 (9) |
Si53 | 0.081 (1) | 0.049 (1) | 0.056 (1) | −0.0009 (10) | 0.021 (1) | 0.0009 (9) |
O4 | 0.043 (2) | 0.039 (2) | 0.043 (2) | 0.002 (2) | 0.008 (2) | −0.004 (2) |
O5 | 0.088 (4) | 0.050 (3) | 0.062 (3) | −0.002 (3) | 0.030 (3) | 0.007 (2) |
O6 | 0.103 (4) | 0.050 (3) | 0.054 (3) | 0.010 (3) | 0.019 (3) | −0.018 (2) |
O7 | 0.081 (3) | 0.047 (3) | 0.050 (3) | −0.009 (2) | 0.003 (2) | 0.005 (2) |
O8 | 0.059 (3) | 0.047 (3) | 0.037 (2) | 0.002 (2) | 0.007 (2) | −0.002 (2) |
O9 | 0.059 (3) | 0.034 (2) | 0.086 (3) | 0.001 (2) | 0.012 (3) | 0.002 (2) |
O54 | 0.041 (2) | 0.036 (2) | 0.040 (2) | 0.007 (2) | 0.003 (2) | −0.003 (2) |
O55 | 0.049 (2) | 0.043 (2) | 0.047 (2) | −0.002 (2) | 0.011 (2) | −0.004 (2) |
O56 | 0.068 (3) | 0.042 (2) | 0.048 (3) | −0.002 (2) | 0.009 (2) | −0.015 (2) |
O57 | 0.090 (4) | 0.052 (3) | 0.055 (3) | −0.009 (3) | −0.008 (3) | 0.014 (2) |
O58 | 0.078 (3) | 0.045 (2) | 0.038 (2) | 0.005 (2) | 0.011 (2) | −0.002 (2) |
O59 | 0.058 (3) | 0.035 (3) | 0.109 (4) | 0.003 (2) | 0.018 (3) | 0.012 (3) |
C10 | 0.061 (4) | 0.083 (6) | 0.062 (4) | 0.021 (4) | −0.020 (4) | −0.016 (4) |
C11 | 0.096 (6) | 0.075 (5) | 0.045 (4) | 0.026 (5) | −0.005 (4) | 0.013 (4) |
C12 | 0.093 (5) | 0.057 (4) | 0.043 (4) | −0.002 (4) | 0.016 (3) | 0.002 (3) |
C13 | 0.029 (3) | 0.032 (3) | 0.046 (3) | −0.001 (2) | 0.005 (2) | −0.004 (2) |
C14 | 0.044 (3) | 0.034 (3) | 0.045 (3) | −0.001 (3) | 0.000 (3) | −0.005 (3) |
C15 | 0.046 (3) | 0.037 (3) | 0.043 (3) | 0.002 (3) | 0.007 (3) | 0.003 (3) |
C16 | 0.068 (4) | 0.047 (4) | 0.046 (4) | 0.007 (3) | 0.008 (3) | −0.011 (3) |
C17 | 0.078 (5) | 0.039 (3) | 0.046 (4) | −0.001 (3) | 0.019 (3) | −0.006 (3) |
C18 | 0.061 (4) | 0.041 (4) | 0.049 (4) | 0.010 (3) | 0.017 (3) | 0.003 (3) |
C19 | 0.038 (3) | 0.033 (3) | 0.060 (4) | 0.000 (3) | 0.013 (3) | −0.001 (3) |
C20 | 0.043 (3) | 0.042 (4) | 0.062 (4) | 0.002 (3) | 0.005 (3) | −0.006 (3) |
C21 | 0.099 (6) | 0.051 (4) | 0.066 (5) | 0.017 (4) | 0.003 (4) | 0.010 (4) |
C22 | 0.095 (6) | 0.042 (4) | 0.047 (4) | −0.001 (4) | −0.005 (4) | 0.012 (3) |
C23 | 0.116 (7) | 0.074 (6) | 0.068 (5) | 0.028 (5) | 0.005 (5) | 0.009 (4) |
C24 | 0.17 (1) | 0.090 (8) | 0.112 (9) | 0.041 (8) | 0.045 (9) | 0.000 (7) |
C25 | 0.27 (2) | 0.087 (9) | 0.090 (9) | 0.02 (1) | 0.04 (1) | −0.006 (7) |
C26 | 0.25 (2) | 0.096 (9) | 0.059 (7) | −0.027 (10) | −0.022 (9) | −0.002 (6) |
C27 | 0.116 (8) | 0.088 (7) | 0.081 (6) | −0.010 (6) | −0.017 (6) | 0.010 (5) |
C28 | 0.140 (8) | 0.067 (5) | 0.063 (5) | 0.000 (5) | 0.031 (5) | 0.016 (4) |
C29 | 0.127 (8) | 0.069 (5) | 0.079 (6) | 0.012 (5) | 0.041 (5) | −0.012 (5) |
C30 | 0.047 (3) | 0.033 (3) | 0.038 (3) | 0.002 (3) | 0.006 (3) | 0.000 (2) |
C31 | 0.073 (4) | 0.035 (3) | 0.050 (4) | −0.002 (3) | 0.014 (3) | 0.000 (3) |
C32 | 0.049 (4) | 0.054 (4) | 0.043 (3) | 0.009 (3) | 0.001 (3) | −0.004 (3) |
C33 | 0.045 (3) | 0.039 (3) | 0.039 (3) | 0.001 (3) | 0.012 (3) | 0.000 (3) |
C34 | 0.058 (4) | 0.036 (3) | 0.048 (4) | −0.002 (3) | 0.011 (3) | −0.002 (3) |
C35 | 0.068 (4) | 0.042 (4) | 0.053 (4) | 0.002 (3) | 0.018 (3) | −0.003 (3) |
C36 | 0.057 (4) | 0.082 (6) | 0.086 (5) | −0.002 (4) | 0.021 (4) | 0.011 (4) |
C37 | 0.149 (9) | 0.066 (6) | 0.123 (8) | −0.037 (6) | 0.074 (7) | −0.009 (5) |
C38 | 0.085 (6) | 0.117 (8) | 0.044 (4) | 0.001 (5) | 0.009 (4) | 0.015 (4) |
C39 | 0.111 (8) | 0.20 (1) | 0.093 (7) | 0.052 (9) | 0.016 (6) | 0.055 (8) |
C40 | 0.142 (9) | 0.132 (10) | 0.075 (6) | −0.043 (8) | −0.014 (6) | −0.022 (6) |
C41 | 0.151 (10) | 0.20 (1) | 0.048 (5) | 0.006 (10) | 0.039 (6) | −0.004 (7) |
C60 | 0.053 (4) | 0.057 (4) | 0.059 (4) | 0.010 (3) | −0.007 (3) | −0.006 (3) |
C61 | 0.093 (6) | 0.059 (5) | 0.052 (4) | 0.015 (4) | −0.004 (4) | 0.008 (4) |
C62 | 0.095 (5) | 0.046 (4) | 0.039 (3) | −0.006 (4) | 0.004 (3) | 0.009 (3) |
C63 | 0.029 (3) | 0.026 (3) | 0.046 (3) | 0.001 (2) | 0.009 (2) | −0.003 (2) |
C64 | 0.035 (3) | 0.035 (3) | 0.046 (3) | 0.000 (3) | 0.007 (3) | −0.003 (3) |
C65 | 0.032 (3) | 0.034 (3) | 0.040 (3) | 0.000 (2) | 0.001 (2) | −0.003 (2) |
C66 | 0.036 (3) | 0.039 (3) | 0.047 (3) | −0.005 (3) | 0.003 (3) | −0.004 (3) |
C67 | 0.044 (3) | 0.042 (3) | 0.041 (3) | −0.006 (3) | 0.007 (3) | −0.009 (3) |
C68 | 0.046 (3) | 0.037 (3) | 0.046 (3) | 0.005 (3) | 0.006 (3) | −0.001 (3) |
C69 | 0.037 (3) | 0.033 (3) | 0.042 (3) | 0.005 (3) | 0.002 (3) | −0.004 (3) |
C70 | 0.044 (3) | 0.045 (4) | 0.052 (4) | 0.003 (3) | −0.003 (3) | −0.001 (3) |
C71 | 0.130 (7) | 0.052 (4) | 0.049 (4) | 0.017 (5) | −0.005 (4) | 0.010 (4) |
C72 | 0.104 (6) | 0.053 (4) | 0.053 (4) | 0.012 (4) | 0.008 (4) | 0.015 (4) |
C73 | 0.122 (8) | 0.118 (9) | 0.088 (7) | 0.037 (7) | 0.029 (6) | 0.010 (6) |
C74 | 0.16 (1) | 0.14 (1) | 0.14 (1) | 0.049 (10) | 0.070 (10) | 0.015 (10) |
C75 | 0.24 (2) | 0.12 (1) | 0.085 (9) | 0.03 (1) | 0.04 (1) | 0.005 (8) |
C76 | 0.24 (2) | 0.12 (1) | 0.075 (8) | 0.01 (1) | −0.045 (9) | −0.012 (7) |
C77 | 0.151 (10) | 0.090 (7) | 0.096 (7) | 0.044 (7) | −0.026 (7) | 0.005 (6) |
C78 | 0.043 (4) | 0.084 (5) | 0.062 (4) | −0.002 (4) | 0.016 (3) | −0.015 (4) |
C79 | 0.078 (5) | 0.074 (5) | 0.053 (4) | −0.014 (4) | 0.001 (4) | −0.023 (4) |
C80 | 0.043 (3) | 0.031 (3) | 0.039 (3) | 0.000 (2) | 0.005 (2) | −0.004 (2) |
C81 | 0.065 (4) | 0.037 (3) | 0.044 (4) | 0.007 (3) | 0.013 (3) | 0.004 (3) |
C82 | 0.055 (4) | 0.048 (4) | 0.044 (3) | 0.005 (3) | 0.000 (3) | −0.010 (3) |
C83 | 0.049 (3) | 0.039 (3) | 0.035 (3) | 0.000 (3) | 0.012 (3) | −0.001 (3) |
C84 | 0.056 (4) | 0.038 (3) | 0.042 (3) | −0.001 (3) | 0.014 (3) | 0.001 (3) |
C85 | 0.066 (4) | 0.041 (4) | 0.072 (5) | 0.006 (3) | 0.019 (4) | 0.002 (3) |
C86 | 0.063 (4) | 0.080 (5) | 0.073 (5) | −0.007 (4) | 0.021 (4) | 0.000 (4) |
C87 | 0.135 (8) | 0.063 (5) | 0.102 (7) | −0.019 (6) | 0.053 (6) | 0.006 (5) |
C88 | 0.103 (6) | 0.082 (6) | 0.057 (5) | 0.013 (5) | 0.016 (4) | 0.002 (4) |
C89 | 0.098 (7) | 0.137 (9) | 0.080 (6) | 0.030 (7) | 0.007 (5) | 0.027 (6) |
C90 | 0.100 (7) | 0.097 (7) | 0.081 (6) | −0.022 (6) | 0.000 (5) | −0.029 (5) |
C91 | 0.17 (1) | 0.17 (1) | 0.051 (5) | 0.015 (9) | 0.038 (6) | 0.017 (6) |
S1—C10 | 1.805 (7) | C35—H35B | 0.96 |
S1—C13 | 1.859 (5) | C36—H36A | 0.96 |
S2—C12 | 1.807 (7) | C36—H36B | 0.97 |
S2—C13 | 1.843 (6) | C36—H36C | 0.96 |
S51—C60 | 1.807 (7) | C37—H37A | 0.96 |
S51—C63 | 1.861 (5) | C37—H37B | 0.97 |
S52—C62 | 1.829 (7) | C37—H37C | 0.98 |
S52—C63 | 1.836 (5) | C38—C39 | 1.52 (2) |
Si3—O8 | 1.648 (4) | C38—C40 | 1.53 (2) |
Si3—C36 | 1.856 (8) | C38—C41 | 1.55 (1) |
Si3—C37 | 1.864 (10) | C39—H39A | 0.96 |
Si3—C38 | 1.878 (8) | C39—H39B | 0.95 |
Si53—O58 | 1.663 (5) | C39—H39C | 0.99 |
Si53—C86 | 1.845 (8) | C40—H40A | 0.96 |
Si53—C87 | 1.853 (9) | C40—H40B | 0.97 |
Si53—C88 | 1.876 (8) | C40—H40C | 1.01 |
O4—C15 | 1.442 (7) | C41—H41A | 0.99 |
O4—C19 | 1.420 (7) | C41—H41B | 0.93 |
O5—C17 | 1.434 (8) | C41—H41C | 0.99 |
O5—C28 | 1.421 (9) | C60—C61 | 1.52 (1) |
O6—C17 | 1.421 (8) | C60—H60A | 0.95 |
O6—C29 | 1.43 (1) | C60—H60B | 0.96 |
O7—C20 | 1.418 (8) | C61—C62 | 1.49 (1) |
O7—C21 | 1.424 (9) | C61—H61A | 0.95 |
O8—C33 | 1.446 (7) | C61—H61B | 0.98 |
O9—C35 | 1.429 (8) | C62—H62A | 0.96 |
O9—H9 | 0.97 (5) | C62—H62B | 0.94 |
O54—C65 | 1.419 (6) | C63—C64 | 1.564 (8) |
O54—C69 | 1.432 (7) | C63—C80 | 1.598 (8) |
O55—C67 | 1.417 (7) | C64—C65 | 1.535 (8) |
O55—C78 | 1.410 (8) | C64—H64A | 0.96 |
O56—C67 | 1.416 (7) | C64—H64B | 0.97 |
O56—C79 | 1.416 (8) | C65—C66 | 1.544 (8) |
O57—C70 | 1.418 (8) | C65—H65 | 0.98 |
O57—C71 | 1.419 (9) | C66—C67 | 1.513 (8) |
O58—C83 | 1.439 (7) | C66—H66A | 0.96 |
O59—C85 | 1.421 (8) | C66—H66B | 0.99 |
O59—H59 | 0.98 (5) | C67—C68 | 1.513 (8) |
C10—C11 | 1.50 (1) | C68—C69 | 1.529 (8) |
C10—H10A | 0.96 | C68—H68A | 0.96 |
C10—H10B | 0.97 | C68—H68B | 0.95 |
C11—C12 | 1.54 (1) | C69—C70 | 1.495 (8) |
C11—H11A | 0.95 | C69—H69 | 0.99 |
C11—H11B | 0.98 | C70—H70A | 0.98 |
C12—H12A | 0.97 | C70—H70B | 0.97 |
C12—H12B | 0.96 | C71—C72 | 1.52 (1) |
C13—C14 | 1.564 (8) | C71—H71A | 0.96 |
C13—C30 | 1.595 (8) | C71—H71B | 0.97 |
C14—C15 | 1.525 (8) | C72—C73 | 1.34 (1) |
C14—H14A | 0.95 | C72—C77 | 1.37 (1) |
C14—H14B | 0.98 | C73—C74 | 1.37 (2) |
C15—C16 | 1.520 (8) | C73—H73 | 0.99 |
C15—H15 | 0.98 | C74—C75 | 1.35 (2) |
C16—C17 | 1.513 (10) | C74—H74 | 1.04 |
C16—H16A | 0.96 | C75—C76 | 1.33 (3) |
C16—H16B | 0.99 | C75—H75 | 1.01 |
C17—C18 | 1.503 (9) | C76—C77 | 1.41 (2) |
C18—C19 | 1.543 (9) | C76—H76 | 0.99 |
C18—H18A | 0.97 | C77—H77 | 0.96 |
C18—H18B | 0.96 | C78—H78A | 0.98 |
C19—C20 | 1.504 (9) | C78—H78B | 0.96 |
C19—H19 | 0.98 | C78—H78C | 0.97 |
C20—H20A | 0.98 | C79—H79A | 0.99 |
C20—H20B | 0.96 | C79—H79B | 0.97 |
C21—C22 | 1.50 (1) | C79—H79C | 0.97 |
C21—H21A | 0.96 | C80—C81 | 1.540 (8) |
C21—H21B | 0.96 | C80—C82 | 1.518 (8) |
C22—C23 | 1.36 (1) | C80—C83 | 1.572 (8) |
C22—C27 | 1.37 (1) | C81—H81A | 0.96 |
C23—C24 | 1.38 (2) | C81—H81B | 0.96 |
C23—H23 | 0.99 | C81—H81C | 0.96 |
C24—C25 | 1.34 (2) | C82—H82A | 0.97 |
C24—H24 | 1.026 | C82—H82B | 0.97 |
C25—C26 | 1.35 (3) | C82—H82C | 0.98 |
C25—H25 | 1.01 | C83—C84 | 1.529 (8) |
C26—C27 | 1.40 (2) | C83—H83 | 0.98 |
C26—H26 | 0.98 | C84—C85 | 1.496 (9) |
C27—H27 | 0.98 | C84—H84A | 0.95 |
C28—H28A | 0.97 | C84—H84B | 0.99 |
C28—H28B | 0.95 | C85—H85A | 0.95 |
C28—H28C | 0.95 | C85—H85B | 0.98 |
C29—H29A | 0.97 | C86—H86A | 0.98 |
C29—H29B | 0.95 | C86—H86B | 0.94 |
C29—H29C | 0.98 | C86—H86C | 0.96 |
C30—C31 | 1.543 (8) | C87—H87A | 0.92 |
C30—C32 | 1.540 (8) | C87—H87B | 0.97 |
C30—C33 | 1.582 (8) | C87—H87C | 1.00 |
C31—H31A | 0.95 | C88—C89 | 1.55 (1) |
C31—H31B | 0.96 | C88—C90 | 1.57 (1) |
C31—H31C | 0.97 | C88—C91 | 1.58 (1) |
C32—H32A | 0.98 | C89—H89A | 0.93 |
C32—H32B | 0.94 | C89—H89B | 0.96 |
C32—H32C | 0.97 | C89—H89C | 1.01 |
C33—C34 | 1.526 (8) | C90—H90A | 0.98 |
C33—H33 | 0.98 | C90—H90B | 0.98 |
C34—C35 | 1.505 (9) | C90—H90C | 0.96 |
C34—H34A | 0.97 | C91—H91A | 0.92 |
C34—H34B | 0.96 | C91—H91B | 0.97 |
C35—H35A | 0.97 | C91—H91C | 0.99 |
C10—S1—C13 | 103.5 (3) | H39A—C39—H39C | 106 |
C12—S2—C13 | 103.2 (3) | H39B—C39—H39C | 107 |
C60—S51—C63 | 104.8 (3) | C38—C40—H40A | 113 |
C62—S52—C63 | 102.7 (3) | C38—C40—H40B | 113 |
O8—Si3—C36 | 113.7 (3) | C38—C40—H40C | 111 |
O8—Si3—C37 | 113.3 (4) | H40A—C40—H40B | 108 |
O8—Si3—C38 | 103.8 (3) | H40A—C40—H40C | 105 |
C36—Si3—C37 | 105.5 (4) | H40B—C40—H40C | 105 |
C36—Si3—C38 | 111.1 (4) | C38—C41—H41A | 109 |
C37—Si3—C38 | 109.5 (4) | C38—C41—H41B | 114 |
O58—Si53—C86 | 115.4 (3) | C38—C41—H41C | 109 |
O58—Si53—C87 | 114.4 (4) | H41A—C41—H41B | 109 |
O58—Si53—C88 | 101.9 (3) | H41A—C41—H41C | 105 |
C86—Si53—C87 | 104.1 (4) | H41B—C41—H41C | 109 |
C86—Si53—C88 | 111.2 (4) | S51—C60—C61 | 113.7 (5) |
C87—Si53—C88 | 110.1 (4) | S51—C60—H60A | 109 |
C15—O4—C19 | 111.2 (4) | S51—C60—H60B | 108 |
C17—O5—C28 | 115.8 (6) | C61—C60—H60A | 108 |
C17—O6—C29 | 115.2 (6) | C61—C60—H60B | 109 |
C20—O7—C21 | 112.8 (5) | H60A—C60—H60B | 109 |
Si3—O8—C33 | 128.8 (4) | C60—C61—C62 | 113.6 (6) |
C35—O9—H9 | 103 (3) | C60—C61—H61A | 110 |
C65—O54—C69 | 112.9 (4) | C60—C61—H61B | 108 |
C67—O55—C78 | 115.6 (5) | C62—C61—H61A | 110 |
C67—O56—C79 | 117.1 (5) | C62—C61—H61B | 108 |
C70—O57—C71 | 114.7 (6) | H61A—C61—H61B | 107 |
Si53—O58—C83 | 128.8 (4) | S52—C62—C61 | 114.5 (5) |
C85—O59—H59 | 109 (3) | S52—C62—H62A | 108 |
S1—C10—C11 | 115.0 (5) | S52—C62—H62B | 108 |
S1—C10—H10A | 109 | C61—C62—H62A | 109 |
S1—C10—H10B | 109 | C61—C62—H62B | 108 |
C11—C10—H10A | 108 | H62A—C62—H62B | 109 |
C11—C10—H10B | 108 | S51—C63—S52 | 109.7 (3) |
H10A—C10—H10B | 109 | S51—C63—C64 | 105.6 (3) |
C10—C11—C12 | 113.4 (6) | S51—C63—C80 | 106.9 (3) |
C10—C11—H11A | 111 | S52—C63—C64 | 108.4 (4) |
C10—C11—H11B | 109 | S52—C63—C80 | 110.7 (3) |
C12—C11—H11A | 109 | C64—C63—C80 | 115.2 (4) |
C12—C11—H11B | 107 | C63—C64—C65 | 120.6 (4) |
H11A—C11—H11B | 108 | C63—C64—H64A | 107 |
S2—C12—C11 | 113.8 (5) | C63—C64—H64B | 107 |
S2—C12—H12A | 109 | C65—C64—H64A | 107 |
S2—C12—H12B | 109 | C65—C64—H64B | 107 |
C11—C12—H12A | 109 | H64A—C64—H64B | 109 |
C11—C12—H12B | 108 | O54—C65—C64 | 109.7 (4) |
H12A—C12—H12B | 108 | O54—C65—C66 | 108.7 (4) |
S1—C13—S2 | 109.6 (3) | O54—C65—H65 | 109 |
S1—C13—C14 | 106.1 (3) | C64—C65—C66 | 110.0 (4) |
S1—C13—C30 | 106.8 (4) | C64—C65—H65 | 110 |
S2—C13—C14 | 109.1 (4) | C66—C65—H65 | 110 |
S2—C13—C30 | 109.6 (4) | C65—C66—C67 | 113.4 (5) |
C14—C13—C30 | 115.6 (4) | C65—C66—H66A | 108 |
C13—C14—C15 | 120.1 (5) | C65—C66—H66B | 108 |
C13—C14—H14A | 107 | C67—C66—H66A | 111 |
C13—C14—H14B | 106 | C67—C66—H66B | 110 |
C15—C14—H14A | 108 | H66A—C66—H66B | 107 |
C15—C14—H14B | 107 | O55—C67—O56 | 110.4 (5) |
H14A—C14—H14B | 109 | O55—C67—C66 | 105.2 (5) |
O4—C15—C14 | 109.4 (4) | O55—C67—C68 | 113.2 (5) |
O4—C15—C16 | 107.8 (5) | O56—C67—C66 | 112.1 (5) |
O4—C15—H15 | 109 | O56—C67—C68 | 105.6 (5) |
C14—C15—C16 | 111.8 (5) | C66—C67—C68 | 110.5 (5) |
C14—C15—H15 | 110 | C67—C68—C69 | 112.8 (5) |
C16—C15—H15 | 110 | C67—C68—H68A | 109 |
C15—C16—C17 | 111.2 (5) | C67—C68—H68B | 110 |
C15—C16—H16A | 110 | C69—C68—H68A | 107 |
C15—C16—H16B | 109 | C69—C68—H68B | 109 |
C17—C16—H16A | 111 | H68A—C68—H68B | 110 |
C17—C16—H16B | 109 | O54—C69—C68 | 109.3 (4) |
H16A—C16—H16B | 107 | O54—C69—C70 | 107.3 (4) |
O5—C17—O6 | 109.9 (5) | O54—C69—H69 | 108 |
O5—C17—C16 | 112.1 (5) | C68—C69—C70 | 113.2 (5) |
O5—C17—C18 | 105.2 (5) | C68—C69—H69 | 109 |
O6—C17—C16 | 104.7 (5) | C70—C69—H69 | 110 |
O6—C17—C18 | 113.5 (5) | O57—C70—C69 | 108.5 (5) |
C16—C17—C18 | 111.6 (5) | O57—C70—H70A | 110 |
C17—C18—C19 | 111.4 (5) | O57—C70—H70B | 110 |
C17—C18—H18A | 109 | C69—C70—H70A | 111 |
C17—C18—H18B | 110 | C69—C70—H70B | 110 |
C19—C18—H18A | 108 | H70A—C70—H70B | 108 |
C19—C18—H18B | 109 | O57—C71—C72 | 113.8 (6) |
H18A—C18—H18B | 109 | O57—C71—H71A | 109 |
O4—C19—C18 | 110.5 (5) | O57—C71—H71B | 108 |
O4—C19—C20 | 107.7 (5) | C72—C71—H71A | 108 |
O4—C19—H19 | 108 | C72—C71—H71B | 108 |
C18—C19—C20 | 113.2 (5) | H71A—C71—H71B | 109 |
C18—C19—H19 | 108 | C71—C72—C73 | 121.0 (8) |
C20—C19—H19 | 109 | C71—C72—C77 | 120.2 (8) |
O7—C20—C19 | 108.3 (5) | C73—C72—C77 | 118.8 (8) |
O7—C20—H20A | 110 | C72—C73—C74 | 121 (1) |
O7—C20—H20B | 111 | C72—C73—H73 | 117 |
C19—C20—H20A | 109 | C74—C73—H73 | 121 |
C19—C20—H20B | 110 | C73—C74—C75 | 119 (1) |
H20A—C20—H20B | 108 | C73—C74—H74 | 116 |
O7—C21—C22 | 113.4 (6) | C75—C74—H74 | 124 |
O7—C21—H21A | 108 | C74—C75—C76 | 122 (1) |
O7—C21—H21B | 109 | C74—C75—H75 | 119 |
C22—C21—H21A | 108 | C76—C75—H75 | 117 |
C22—C21—H21B | 109 | C75—C76—C77 | 117 (1) |
H21A—C21—H21B | 109 | C75—C76—H76 | 123 |
C21—C22—C23 | 121.2 (7) | C77—C76—H76 | 118 |
C21—C22—C27 | 119.9 (8) | C72—C77—C76 | 120 (1) |
C23—C22—C27 | 118.8 (7) | C72—C77—H77 | 117 |
C22—C23—C24 | 120.5 (9) | C76—C77—H77 | 121 |
C22—C23—H23 | 118 | O55—C78—H78A | 110 |
C24—C23—H23 | 121 | O55—C78—H78B | 112 |
C23—C24—C25 | 121 (1) | O55—C78—H78C | 111 |
C23—C24—H24 | 117 | H78A—C78—H78B | 108 |
C25—C24—H24 | 121 | H78A—C78—H78C | 107 |
C24—C25—C26 | 119 (1) | H78B—C78—H78C | 109 |
C24—C25—H25 | 117 | O56—C79—H79A | 111 |
C26—C25—H25 | 123 | O56—C79—H79B | 112 |
C25—C26—C27 | 120 (1) | O56—C79—H79C | 112 |
C25—C26—H26 | 121 | H79A—C79—H79B | 107 |
C27—C26—H26 | 117 | H79A—C79—H79C | 107 |
C22—C27—C26 | 119 (1) | H79B—C79—H79C | 108 |
C22—C27—H27 | 119 | C63—C80—C81 | 108.2 (4) |
C26—C27—H27 | 122 | C63—C80—C82 | 110.7 (4) |
O5—C28—H28A | 109 | C63—C80—C83 | 112.8 (4) |
O5—C28—H28B | 109 | C81—C80—C82 | 108.5 (5) |
O5—C28—H28C | 110 | C81—C80—C83 | 107.5 (5) |
H28A—C28—H28B | 109 | C82—C80—C83 | 109.0 (5) |
H28A—C28—H28C | 109 | C80—C81—H81A | 110 |
H28B—C28—H28C | 111 | C80—C81—H81B | 109 |
O6—C29—H29A | 112 | C80—C81—H81C | 109 |
O6—C29—H29B | 111 | H81A—C81—H81B | 110 |
O6—C29—H29C | 110 | H81A—C81—H81C | 110 |
H29A—C29—H29B | 110 | H81B—C81—H81C | 110 |
H29A—C29—H29C | 107 | C80—C82—H82A | 111 |
H29B—C29—H29C | 108 | C80—C82—H82B | 111 |
C13—C30—C31 | 108.0 (4) | C80—C82—H82C | 111 |
C13—C30—C32 | 111.7 (4) | H82A—C82—H82B | 109 |
C13—C30—C33 | 113.4 (4) | H82A—C82—H82C | 108 |
C31—C30—C32 | 107.0 (5) | H82B—C82—H82C | 108 |
C31—C30—C33 | 107.0 (5) | O58—C83—C80 | 107.7 (4) |
C32—C30—C33 | 109.4 (5) | O58—C83—C84 | 108.8 (4) |
C30—C31—H31A | 111 | O58—C83—H83 | 108 |
C30—C31—H31B | 109 | C80—C83—C84 | 116.5 (5) |
C30—C31—H31C | 109 | C80—C83—H83 | 108 |
H31A—C31—H31B | 110 | C84—C83—H83 | 108 |
H31A—C31—H31C | 109 | C83—C84—C85 | 112.8 (5) |
H31B—C31—H31C | 109 | C83—C84—H84A | 110 |
C30—C32—H32A | 109 | C83—C84—H84B | 109 |
C30—C32—H32B | 111 | C85—C84—H84A | 109 |
C30—C32—H32C | 110 | C85—C84—H84B | 108 |
H32A—C32—H32B | 109 | H84A—C84—H84B | 108 |
H32A—C32—H32C | 107 | O59—C85—C84 | 110.5 (5) |
H32B—C32—H32C | 110 | O59—C85—H85A | 110 |
O8—C33—C30 | 108.6 (4) | O59—C85—H85B | 109 |
O8—C33—C34 | 108.3 (4) | C84—C85—H85A | 110 |
O8—C33—H33 | 108 | C84—C85—H85B | 109 |
C30—C33—C34 | 114.9 (5) | H85A—C85—H85B | 109 |
C30—C33—H33 | 109 | Si53—C86—H86A | 109 |
C34—C33—H33 | 108 | Si53—C86—H86B | 110 |
C33—C34—C35 | 112.8 (5) | Si53—C86—H86C | 109 |
C33—C34—H34A | 109 | H86A—C86—H86B | 109 |
C33—C34—H34B | 110 | H86A—C86—H86C | 108 |
C35—C34—H34A | 108 | H86B—C86—H86C | 111 |
C35—C34—H34B | 109 | Si53—C87—H87A | 113 |
H34A—C34—H34B | 108 | Si53—C87—H87B | 110 |
O9—C35—C34 | 109.7 (5) | Si53—C87—H87C | 108 |
O9—C35—H35A | 109 | H87A—C87—H87B | 111 |
O9—C35—H35B | 110 | H87A—C87—H87C | 109 |
C34—C35—H35A | 110 | H87B—C87—H87C | 105 |
C34—C35—H35B | 110 | Si53—C88—C89 | 108.7 (6) |
H35A—C35—H35B | 108 | Si53—C88—C90 | 108.7 (5) |
Si3—C36—H36A | 110 | Si53—C88—C91 | 108.6 (6) |
Si3—C36—H36B | 109 | C89—C88—C90 | 109.6 (8) |
Si3—C36—H36C | 110 | C89—C88—C91 | 111.5 (8) |
H36A—C36—H36B | 109 | C90—C88—C91 | 109.7 (8) |
H36A—C36—H36C | 110 | C88—C89—H89A | 112 |
H36B—C36—H36C | 109 | C88—C89—H89B | 111 |
Si3—C37—H37A | 112 | C88—C89—H89C | 109 |
Si3—C37—H37B | 111 | H89A—C89—H89B | 111 |
Si3—C37—H37C | 110 | H89A—C89—H89C | 108 |
H37A—C37—H37B | 108 | H89B—C89—H89C | 106 |
H37A—C37—H37C | 108 | C88—C90—H90A | 111 |
H37B—C37—H37C | 107 | C88—C90—H90B | 111 |
Si3—C38—C39 | 110.8 (7) | C88—C90—H90C | 114 |
Si3—C38—C40 | 109.9 (6) | H90A—C90—H90B | 106 |
Si3—C38—C41 | 110.1 (6) | H90A—C90—H90C | 108 |
C39—C38—C40 | 107.9 (8) | H90B—C90—H90C | 108 |
C39—C38—C41 | 108.6 (8) | C88—C91—H91A | 111 |
C40—C38—C41 | 109.5 (8) | C88—C91—H91B | 109 |
C38—C39—H39A | 110 | C88—C91—H91C | 107 |
C38—C39—H39B | 112 | H91A—C91—H91B | 111 |
C38—C39—H39C | 109 | H91A—C91—H91C | 110 |
H39A—C39—H39B | 110 | H91B—C91—H91C | 106 |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9···O4i | 0.97 (5) | 2.17 (6) | 3.035 (6) | 147 (5) |
O9—H9···O7i | 0.97 (5) | 2.41 (4) | 3.188 (7) | 136 (5) |
O59—H59···O54ii | 0.98 (5) | 2.30 (6) | 3.096 (6) | 138 (5) |
O59—H59···O57ii | 0.98 (5) | 2.28 (5) | 3.082 (7) | 139 (5) |
Symmetry codes: (i) −x, y+1/2, −z+2; (ii) −x−1, y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C32H56O6S2Si |
Mr | 629.00 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 6.878 (3), 19.658 (3), 26.493 (2) |
β (°) | 91.33 (2) |
V (Å3) | 3581.1 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.7 × 0.6 × 0.1 |
Data collection | |
Diffractometer | Rigaku AFC5 diffractometer |
Absorption correction | Integration (Coppens et al., 1965) |
Tmin, Tmax | 0.881, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7078, 6497, 4622 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.130, 1.02 |
No. of reflections | 6497 |
No. of parameters | 745 |
No. of restraints | ? |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.00, −0.29 |
Absolute structure | Flack (1983), no Friedel pairs |
Absolute structure parameter | 0.0 (1) |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), TEXSAN.
S1—C10 | 1.805 (7) | Si3—O8 | 1.648 (4) |
S1—C13 | 1.859 (5) | Si3—C36 | 1.856 (8) |
S2—C12 | 1.807 (7) | Si3—C37 | 1.864 (10) |
S2—C13 | 1.843 (6) | Si3—C38 | 1.878 (8) |
S51—C60 | 1.807 (7) | Si53—O58 | 1.663 (5) |
S51—C63 | 1.861 (5) | Si53—C86 | 1.845 (8) |
S52—C62 | 1.829 (7) | Si53—C87 | 1.853 (9) |
S52—C63 | 1.836 (5) | Si53—C88 | 1.876 (8) |
Si3—O8—C33 | 128.8 (4) | Si53—O58—C83 | 128.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9···O4i | 0.97 (5) | 2.17 (6) | 3.035 (6) | 147 (5) |
O9—H9···O7i | 0.97 (5) | 2.41 (4) | 3.188 (7) | 136 (5) |
O59—H59···O54ii | 0.98 (5) | 2.30 (6) | 3.096 (6) | 138 (5) |
O59—H59···O57ii | 0.98 (5) | 2.28 (5) | 3.082 (7) | 139 (5) |
Symmetry codes: (i) −x, y+1/2, −z+2; (ii) −x−1, y+1/2, −z+1. |
A synthetic study on bryostatin 3 has been reported (Obitsu et al., 1998).