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The absolute configuration was determined for the title compound, (-)-C32H56O6S2Si, (I), which was prepared in a synthetic study on the natural products bryostatins. Two independent mol­ecules show similar conformations, except for the orientation of the methoxy groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000336X/qa0240sup1.cif
Contains datablocks top, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000336X/qa0240Isup2.hkl
Contains datablock I

CCDC reference: 144699

Comment top

A synthetic study on bryostatin 3 has been reported (Obitsu et al., 1998).

Experimental top

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.

Refinement top

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.

Computing details top

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.

(I) top
Crystal data top
C32H56O6S2SiDx = 1.167 Mg m3
Mr = 629.00Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21Cell parameters from 25 reflections
a = 6.878 (3) Åθ = 14.3–15.0°
b = 19.658 (3) ŵ = 0.22 mm1
c = 26.493 (2) ÅT = 298 K
β = 91.33 (2)°Plate-like, colourless
V = 3581.1 (17) Å30.7 × 0.6 × 0.1 mm
Z = 4
Data collection top
Rigaku AFC5
diffractometer
Rint = 0.030
ω scansθmax = 25°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 08
Tmin = 0.881, Tmax = 0.977k = 023
7078 measured reflectionsl = 3131
6497 independent reflections3 standard reflections every 100 reflections
4622 reflections with I > 2σ(I) intensity decay: 1.0%
Refinement top
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) = 0.130Δρmax = 1.00 e Å3
S = 1.02Δρmin = 0.29 e Å3
6497 reflectionsAbsolute structure: Flack (1983), no Friedel pairs
745 parametersAbsolute structure parameter: 0.0 (1)
H atoms treated by a mixture of independent and constrained refinement
Crystal data top
C32H56O6S2SiV = 3581.1 (17) Å3
Mr = 629.00Z = 4
Monoclinic, P21Mo Kα radiation
a = 6.878 (3) ŵ = 0.22 mm1
b = 19.658 (3) ÅT = 298 K
c = 26.493 (2) Å0.7 × 0.6 × 0.1 mm
β = 91.33 (2)°
Data collection top
Rigaku AFC5
diffractometer
4622 reflections with I > 2σ(I)
Absorption correction: integration
(Coppens et al., 1965)
Rint = 0.030
Tmin = 0.881, Tmax = 0.9773 standard reflections every 100 reflections
7078 measured reflections intensity decay: 1.0%
6497 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130Δρmax = 1.00 e Å3
S = 1.02Δρmin = 0.29 e Å3
6497 reflectionsAbsolute structure: Flack (1983), no Friedel pairs
745 parametersAbsolute structure parameter: 0.0 (1)
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.2505 (2)0.70209 (9)0.94213 (6)0.0492 (4)
S20.1644 (2)0.73805 (7)0.91772 (6)0.0447 (4)
S510.7194 (2)0.74784 (8)0.43871 (6)0.0442 (4)
S520.3093 (2)0.78914 (7)0.41375 (6)0.0433 (4)
Si30.1647 (3)0.7039 (1)1.13615 (7)0.0542 (5)
Si530.6388 (3)0.7629 (1)0.63296 (7)0.0615 (5)
O40.2922 (5)0.5363 (2)0.9461 (1)0.0413 (9)
O50.5343 (7)0.5533 (2)0.8298 (2)0.066 (1)
O60.3625 (8)0.4556 (2)0.8056 (2)0.069 (1)
O70.4612 (7)0.4198 (2)0.9916 (2)0.059 (1)
O80.0036 (6)0.7133 (2)1.0916 (1)0.048 (1)
O90.0102 (7)0.9197 (2)1.0391 (2)0.059 (1)
O540.1691 (5)0.5891 (2)0.4547 (1)0.0391 (9)
O550.0802 (6)0.5872 (2)0.3370 (1)0.046 (1)
O560.0697 (7)0.4819 (2)0.3261 (2)0.052 (1)
O570.0464 (8)0.4773 (2)0.5110 (2)0.066 (1)
O580.4779 (7)0.7729 (2)0.5877 (1)0.053 (1)
O590.5285 (7)0.9752 (2)0.5284 (2)0.067 (1)
C100.287 (1)0.7162 (4)0.8753 (3)0.069 (2)
C110.153 (1)0.7670 (4)0.8525 (3)0.072 (2)
C120.062 (1)0.7445 (4)0.8545 (2)0.064 (2)
C130.0076 (7)0.6744 (3)0.9477 (2)0.036 (1)
C140.0203 (8)0.6059 (3)0.9179 (2)0.041 (1)
C150.2179 (8)0.5767 (3)0.9045 (2)0.042 (1)
C160.204 (1)0.5312 (3)0.8582 (2)0.054 (2)
C170.401 (1)0.5019 (3)0.8458 (2)0.054 (2)
C180.4975 (10)0.4694 (3)0.8912 (2)0.050 (2)
C190.4871 (8)0.5158 (3)0.9380 (2)0.043 (1)
C200.5616 (9)0.4822 (3)0.9857 (3)0.049 (2)
C210.521 (1)0.3838 (4)1.0358 (3)0.072 (2)
C220.446 (1)0.4143 (3)1.0836 (3)0.061 (2)
C230.263 (1)0.4403 (5)1.0856 (3)0.086 (3)
C240.194 (2)0.4653 (6)1.1302 (5)0.124 (4)
C250.304 (3)0.4659 (7)1.1724 (5)0.149 (7)
C260.484 (3)0.4377 (7)1.1719 (4)0.134 (5)
C270.559 (2)0.4127 (5)1.1271 (4)0.095 (3)
C280.471 (1)0.5932 (4)0.7879 (3)0.089 (3)
C290.528 (1)0.4199 (5)0.7878 (3)0.091 (3)
C300.0604 (8)0.6700 (3)1.0065 (2)0.039 (1)
C310.017 (1)0.6017 (3)1.0264 (2)0.052 (2)
C320.2819 (9)0.6702 (3)1.0165 (2)0.049 (2)
C330.0362 (8)0.7282 (3)1.0386 (2)0.041 (1)
C340.0394 (9)0.7998 (3)1.0283 (2)0.047 (2)
C350.0735 (10)0.8540 (3)1.0550 (2)0.054 (2)
C360.376 (1)0.7621 (4)1.1295 (3)0.075 (2)
C370.269 (2)0.6166 (5)1.1387 (4)0.112 (4)
C380.022 (1)0.7215 (5)1.1960 (3)0.082 (3)
C390.148 (2)0.6724 (7)1.2020 (4)0.134 (5)
C400.060 (2)0.7939 (6)1.1948 (4)0.117 (4)
C410.155 (2)0.7137 (7)1.2423 (3)0.133 (5)
C600.7599 (9)0.7573 (4)0.3714 (3)0.056 (2)
C610.627 (1)0.8092 (4)0.3474 (3)0.068 (2)
C620.417 (1)0.7898 (4)0.3500 (2)0.060 (2)
C630.4573 (7)0.7257 (3)0.4462 (2)0.034 (1)
C640.4332 (8)0.6557 (3)0.4189 (2)0.038 (1)
C650.2304 (8)0.6256 (3)0.4109 (2)0.035 (1)
C660.2360 (8)0.5764 (3)0.3655 (2)0.041 (1)
C670.0466 (9)0.5388 (3)0.3584 (2)0.042 (1)
C680.0290 (9)0.5105 (3)0.4082 (2)0.043 (1)
C690.0239 (8)0.5625 (3)0.4511 (2)0.037 (1)
C700.0788 (9)0.5330 (3)0.5014 (2)0.047 (2)
C710.011 (1)0.4363 (4)0.5527 (3)0.077 (2)
C720.028 (1)0.4683 (4)0.6036 (3)0.070 (2)
C730.198 (2)0.4999 (6)0.6120 (4)0.109 (3)
C740.238 (2)0.5257 (7)0.6588 (6)0.144 (5)
C750.107 (3)0.5189 (8)0.6967 (5)0.147 (6)
C760.064 (3)0.4878 (8)0.6908 (4)0.146 (6)
C770.105 (2)0.4627 (6)0.6425 (4)0.113 (4)
C780.2619 (9)0.5619 (4)0.3221 (3)0.063 (2)
C790.150 (1)0.4942 (4)0.2772 (3)0.068 (2)
C800.4074 (8)0.7252 (3)0.5054 (2)0.038 (1)
C810.4774 (10)0.6572 (3)0.5273 (2)0.048 (2)
C820.1896 (9)0.7310 (3)0.5150 (2)0.049 (1)
C830.5125 (8)0.7839 (3)0.5345 (2)0.041 (1)
C840.4531 (9)0.8566 (3)0.5214 (2)0.045 (1)
C850.580 (1)0.9090 (3)0.5449 (3)0.059 (2)
C860.856 (1)0.8177 (4)0.6278 (3)0.072 (2)
C870.739 (2)0.6757 (4)0.6376 (4)0.099 (3)
C880.489 (1)0.7836 (5)0.6911 (3)0.081 (2)
C890.320 (1)0.7322 (6)0.6957 (3)0.105 (3)
C900.406 (1)0.8575 (5)0.6857 (3)0.093 (3)
C910.624 (2)0.7802 (7)0.7382 (3)0.127 (4)
H90.131 (6)0.945 (3)1.035 (2)0.0732*
H10A0.27080.67390.85800.0826*
H10B0.41890.73220.86930.0826*
H11A0.18990.77620.81830.0852*
H11B0.15960.80960.87160.0852*
H12A0.13770.77700.83530.0741*
H12B0.07010.70100.83820.0741*
H14A0.04710.57290.93720.0514*
H14B0.05130.61340.88620.0514*
H150.30870.61400.89840.0500*
H16A0.11140.49560.86340.0673*
H16B0.15510.55860.82920.0673*
H18A0.43190.42720.89860.0598*
H18B0.63120.45980.88430.0598*
H190.56450.55630.93180.0535*
H20A0.53790.51231.01420.0599*
H20B0.69890.47490.98380.0599*
H21A0.47200.33791.03330.0852*
H21B0.66030.38271.03760.0852*
H230.18220.44021.05420.1051*
H240.05270.48231.12990.1629*
H250.24450.48521.20380.1735*
H260.57090.43991.20140.1572*
H270.69090.39341.12550.1111*
H28A0.57170.62660.78050.1034*
H28B0.45280.56440.75920.1034*
H28C0.35410.61660.79530.1034*
H29A0.59280.39430.81460.1028*
H29B0.49230.38990.76090.1028*
H29C0.62400.45250.77510.1028*
H31A0.15460.59861.02090.0649*
H31B0.04630.56491.00960.0649*
H31C0.01200.59871.06230.0649*
H32A0.30770.66691.05300.0598*
H32B0.34230.63331.00030.0598*
H32C0.33790.71271.00530.0598*
H330.17670.72791.03150.0483*
H34A0.17490.80281.03950.0596*
H34B0.03250.80870.99260.0596*
H35A0.05300.85011.09130.0628*
H35B0.21040.84901.04760.0628*
H36A0.33310.80861.13030.0934*
H36B0.44260.75371.09750.0934*
H36C0.46450.75431.15630.0934*
H37A0.36200.61211.16490.1440*
H37B0.33250.60441.10670.1440*
H37C0.16620.58291.14490.1440*
H39A0.10100.62631.20460.1606*
H39B0.23560.67601.17510.1606*
H39C0.22010.68231.23380.1606*
H40A0.12700.80641.22570.1337*
H40B0.14650.80101.16700.1337*
H40C0.04640.82851.18990.1337*
H41A0.07690.72171.27340.1608*
H41B0.26230.74241.24150.1608*
H41C0.19770.66601.24430.1608*
H590.646 (6)1.000 (3)0.518 (3)0.0822*
H60A0.73830.71460.35590.0694*
H60B0.89230.77050.36560.0694*
H61A0.66630.81690.31340.0808*
H61B0.64160.85250.36540.0808*
H62A0.34500.82170.33020.0721*
H62B0.40480.74610.33610.0721*
H64A0.50430.62310.43800.0496*
H64B0.49470.66030.38570.0496*
H650.13810.66230.40490.0427*
H66A0.34070.54470.37030.0501*
H66B0.26880.60320.33510.0501*
H68A0.05230.47290.41780.0515*
H68B0.15950.49520.40460.0515*
H690.11160.60090.44310.0479*
H70A0.06720.56710.52800.0557*
H70B0.21220.51770.50170.0557*
H71A0.05560.39370.55080.0948*
H71B0.14990.42830.55100.0948*
H730.28800.50520.58280.1351*
H740.37370.54850.66250.1798*
H750.13670.53650.73160.1921*
H760.16880.48600.71720.1970*
H770.22100.43730.63660.1390*
H78A0.33360.54300.35120.0811*
H78B0.24740.52700.29710.0811*
H78C0.34170.59820.30850.0811*
H79A0.28160.51400.27900.0805*
H79B0.07320.52600.25810.0805*
H79C0.16240.45270.25800.0805*
H81A0.61480.65250.52130.0587*
H81B0.41040.62070.51120.0587*
H81C0.44920.65650.56290.0587*
H82A0.15960.72960.55080.0588*
H82B0.12240.69410.49890.0588*
H82C0.13880.77350.50190.0588*
H830.65280.77940.52780.0498*
H84A0.32190.86450.53190.0566*
H84B0.46170.86270.48440.0566*
H85A0.56650.90650.58050.0754*
H85B0.71520.90020.53500.0754*
H86A0.81430.86540.62970.0853*
H86B0.92250.81020.59680.0853*
H86C0.93830.80900.65580.0853*
H87A0.82510.67100.66370.1269*
H87B0.79680.66180.60550.1269*
H87C0.62720.64350.64370.1269*
H89A0.36430.68790.70030.1250*
H89B0.23660.73570.66720.1250*
H89C0.23620.74470.72600.1250*
H90A0.32140.86970.71470.1126*
H90B0.32350.86070.65590.1126*
H90C0.50460.89180.68250.1126*
H91A0.55680.78880.76780.1611*
H91B0.73270.81140.73310.1611*
H91C0.68070.73400.73850.1611*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0401 (8)0.0544 (10)0.0532 (10)0.0073 (8)0.0036 (7)0.0045 (8)
S20.0538 (9)0.0369 (8)0.0439 (9)0.0065 (7)0.0119 (7)0.0032 (7)
S510.0357 (7)0.0413 (9)0.0559 (9)0.0062 (7)0.0074 (7)0.0000 (7)
S520.0503 (9)0.0365 (8)0.0437 (8)0.0088 (7)0.0125 (7)0.0030 (7)
Si30.063 (1)0.049 (1)0.051 (1)0.0004 (9)0.0183 (9)0.0017 (9)
Si530.081 (1)0.049 (1)0.056 (1)0.0009 (10)0.021 (1)0.0009 (9)
O40.043 (2)0.039 (2)0.043 (2)0.002 (2)0.008 (2)0.004 (2)
O50.088 (4)0.050 (3)0.062 (3)0.002 (3)0.030 (3)0.007 (2)
O60.103 (4)0.050 (3)0.054 (3)0.010 (3)0.019 (3)0.018 (2)
O70.081 (3)0.047 (3)0.050 (3)0.009 (2)0.003 (2)0.005 (2)
O80.059 (3)0.047 (3)0.037 (2)0.002 (2)0.007 (2)0.002 (2)
O90.059 (3)0.034 (2)0.086 (3)0.001 (2)0.012 (3)0.002 (2)
O540.041 (2)0.036 (2)0.040 (2)0.007 (2)0.003 (2)0.003 (2)
O550.049 (2)0.043 (2)0.047 (2)0.002 (2)0.011 (2)0.004 (2)
O560.068 (3)0.042 (2)0.048 (3)0.002 (2)0.009 (2)0.015 (2)
O570.090 (4)0.052 (3)0.055 (3)0.009 (3)0.008 (3)0.014 (2)
O580.078 (3)0.045 (2)0.038 (2)0.005 (2)0.011 (2)0.002 (2)
O590.058 (3)0.035 (3)0.109 (4)0.003 (2)0.018 (3)0.012 (3)
C100.061 (4)0.083 (6)0.062 (4)0.021 (4)0.020 (4)0.016 (4)
C110.096 (6)0.075 (5)0.045 (4)0.026 (5)0.005 (4)0.013 (4)
C120.093 (5)0.057 (4)0.043 (4)0.002 (4)0.016 (3)0.002 (3)
C130.029 (3)0.032 (3)0.046 (3)0.001 (2)0.005 (2)0.004 (2)
C140.044 (3)0.034 (3)0.045 (3)0.001 (3)0.000 (3)0.005 (3)
C150.046 (3)0.037 (3)0.043 (3)0.002 (3)0.007 (3)0.003 (3)
C160.068 (4)0.047 (4)0.046 (4)0.007 (3)0.008 (3)0.011 (3)
C170.078 (5)0.039 (3)0.046 (4)0.001 (3)0.019 (3)0.006 (3)
C180.061 (4)0.041 (4)0.049 (4)0.010 (3)0.017 (3)0.003 (3)
C190.038 (3)0.033 (3)0.060 (4)0.000 (3)0.013 (3)0.001 (3)
C200.043 (3)0.042 (4)0.062 (4)0.002 (3)0.005 (3)0.006 (3)
C210.099 (6)0.051 (4)0.066 (5)0.017 (4)0.003 (4)0.010 (4)
C220.095 (6)0.042 (4)0.047 (4)0.001 (4)0.005 (4)0.012 (3)
C230.116 (7)0.074 (6)0.068 (5)0.028 (5)0.005 (5)0.009 (4)
C240.17 (1)0.090 (8)0.112 (9)0.041 (8)0.045 (9)0.000 (7)
C250.27 (2)0.087 (9)0.090 (9)0.02 (1)0.04 (1)0.006 (7)
C260.25 (2)0.096 (9)0.059 (7)0.027 (10)0.022 (9)0.002 (6)
C270.116 (8)0.088 (7)0.081 (6)0.010 (6)0.017 (6)0.010 (5)
C280.140 (8)0.067 (5)0.063 (5)0.000 (5)0.031 (5)0.016 (4)
C290.127 (8)0.069 (5)0.079 (6)0.012 (5)0.041 (5)0.012 (5)
C300.047 (3)0.033 (3)0.038 (3)0.002 (3)0.006 (3)0.000 (2)
C310.073 (4)0.035 (3)0.050 (4)0.002 (3)0.014 (3)0.000 (3)
C320.049 (4)0.054 (4)0.043 (3)0.009 (3)0.001 (3)0.004 (3)
C330.045 (3)0.039 (3)0.039 (3)0.001 (3)0.012 (3)0.000 (3)
C340.058 (4)0.036 (3)0.048 (4)0.002 (3)0.011 (3)0.002 (3)
C350.068 (4)0.042 (4)0.053 (4)0.002 (3)0.018 (3)0.003 (3)
C360.057 (4)0.082 (6)0.086 (5)0.002 (4)0.021 (4)0.011 (4)
C370.149 (9)0.066 (6)0.123 (8)0.037 (6)0.074 (7)0.009 (5)
C380.085 (6)0.117 (8)0.044 (4)0.001 (5)0.009 (4)0.015 (4)
C390.111 (8)0.20 (1)0.093 (7)0.052 (9)0.016 (6)0.055 (8)
C400.142 (9)0.132 (10)0.075 (6)0.043 (8)0.014 (6)0.022 (6)
C410.151 (10)0.20 (1)0.048 (5)0.006 (10)0.039 (6)0.004 (7)
C600.053 (4)0.057 (4)0.059 (4)0.010 (3)0.007 (3)0.006 (3)
C610.093 (6)0.059 (5)0.052 (4)0.015 (4)0.004 (4)0.008 (4)
C620.095 (5)0.046 (4)0.039 (3)0.006 (4)0.004 (3)0.009 (3)
C630.029 (3)0.026 (3)0.046 (3)0.001 (2)0.009 (2)0.003 (2)
C640.035 (3)0.035 (3)0.046 (3)0.000 (3)0.007 (3)0.003 (3)
C650.032 (3)0.034 (3)0.040 (3)0.000 (2)0.001 (2)0.003 (2)
C660.036 (3)0.039 (3)0.047 (3)0.005 (3)0.003 (3)0.004 (3)
C670.044 (3)0.042 (3)0.041 (3)0.006 (3)0.007 (3)0.009 (3)
C680.046 (3)0.037 (3)0.046 (3)0.005 (3)0.006 (3)0.001 (3)
C690.037 (3)0.033 (3)0.042 (3)0.005 (3)0.002 (3)0.004 (3)
C700.044 (3)0.045 (4)0.052 (4)0.003 (3)0.003 (3)0.001 (3)
C710.130 (7)0.052 (4)0.049 (4)0.017 (5)0.005 (4)0.010 (4)
C720.104 (6)0.053 (4)0.053 (4)0.012 (4)0.008 (4)0.015 (4)
C730.122 (8)0.118 (9)0.088 (7)0.037 (7)0.029 (6)0.010 (6)
C740.16 (1)0.14 (1)0.14 (1)0.049 (10)0.070 (10)0.015 (10)
C750.24 (2)0.12 (1)0.085 (9)0.03 (1)0.04 (1)0.005 (8)
C760.24 (2)0.12 (1)0.075 (8)0.01 (1)0.045 (9)0.012 (7)
C770.151 (10)0.090 (7)0.096 (7)0.044 (7)0.026 (7)0.005 (6)
C780.043 (4)0.084 (5)0.062 (4)0.002 (4)0.016 (3)0.015 (4)
C790.078 (5)0.074 (5)0.053 (4)0.014 (4)0.001 (4)0.023 (4)
C800.043 (3)0.031 (3)0.039 (3)0.000 (2)0.005 (2)0.004 (2)
C810.065 (4)0.037 (3)0.044 (4)0.007 (3)0.013 (3)0.004 (3)
C820.055 (4)0.048 (4)0.044 (3)0.005 (3)0.000 (3)0.010 (3)
C830.049 (3)0.039 (3)0.035 (3)0.000 (3)0.012 (3)0.001 (3)
C840.056 (4)0.038 (3)0.042 (3)0.001 (3)0.014 (3)0.001 (3)
C850.066 (4)0.041 (4)0.072 (5)0.006 (3)0.019 (4)0.002 (3)
C860.063 (4)0.080 (5)0.073 (5)0.007 (4)0.021 (4)0.000 (4)
C870.135 (8)0.063 (5)0.102 (7)0.019 (6)0.053 (6)0.006 (5)
C880.103 (6)0.082 (6)0.057 (5)0.013 (5)0.016 (4)0.002 (4)
C890.098 (7)0.137 (9)0.080 (6)0.030 (7)0.007 (5)0.027 (6)
C900.100 (7)0.097 (7)0.081 (6)0.022 (6)0.000 (5)0.029 (5)
C910.17 (1)0.17 (1)0.051 (5)0.015 (9)0.038 (6)0.017 (6)
Geometric parameters (Å, º) top
S1—C101.805 (7)C35—H35B0.96
S1—C131.859 (5)C36—H36A0.96
S2—C121.807 (7)C36—H36B0.97
S2—C131.843 (6)C36—H36C0.96
S51—C601.807 (7)C37—H37A0.96
S51—C631.861 (5)C37—H37B0.97
S52—C621.829 (7)C37—H37C0.98
S52—C631.836 (5)C38—C391.52 (2)
Si3—O81.648 (4)C38—C401.53 (2)
Si3—C361.856 (8)C38—C411.55 (1)
Si3—C371.864 (10)C39—H39A0.96
Si3—C381.878 (8)C39—H39B0.95
Si53—O581.663 (5)C39—H39C0.99
Si53—C861.845 (8)C40—H40A0.96
Si53—C871.853 (9)C40—H40B0.97
Si53—C881.876 (8)C40—H40C1.01
O4—C151.442 (7)C41—H41A0.99
O4—C191.420 (7)C41—H41B0.93
O5—C171.434 (8)C41—H41C0.99
O5—C281.421 (9)C60—C611.52 (1)
O6—C171.421 (8)C60—H60A0.95
O6—C291.43 (1)C60—H60B0.96
O7—C201.418 (8)C61—C621.49 (1)
O7—C211.424 (9)C61—H61A0.95
O8—C331.446 (7)C61—H61B0.98
O9—C351.429 (8)C62—H62A0.96
O9—H90.97 (5)C62—H62B0.94
O54—C651.419 (6)C63—C641.564 (8)
O54—C691.432 (7)C63—C801.598 (8)
O55—C671.417 (7)C64—C651.535 (8)
O55—C781.410 (8)C64—H64A0.96
O56—C671.416 (7)C64—H64B0.97
O56—C791.416 (8)C65—C661.544 (8)
O57—C701.418 (8)C65—H650.98
O57—C711.419 (9)C66—C671.513 (8)
O58—C831.439 (7)C66—H66A0.96
O59—C851.421 (8)C66—H66B0.99
O59—H590.98 (5)C67—C681.513 (8)
C10—C111.50 (1)C68—C691.529 (8)
C10—H10A0.96C68—H68A0.96
C10—H10B0.97C68—H68B0.95
C11—C121.54 (1)C69—C701.495 (8)
C11—H11A0.95C69—H690.99
C11—H11B0.98C70—H70A0.98
C12—H12A0.97C70—H70B0.97
C12—H12B0.96C71—C721.52 (1)
C13—C141.564 (8)C71—H71A0.96
C13—C301.595 (8)C71—H71B0.97
C14—C151.525 (8)C72—C731.34 (1)
C14—H14A0.95C72—C771.37 (1)
C14—H14B0.98C73—C741.37 (2)
C15—C161.520 (8)C73—H730.99
C15—H150.98C74—C751.35 (2)
C16—C171.513 (10)C74—H741.04
C16—H16A0.96C75—C761.33 (3)
C16—H16B0.99C75—H751.01
C17—C181.503 (9)C76—C771.41 (2)
C18—C191.543 (9)C76—H760.99
C18—H18A0.97C77—H770.96
C18—H18B0.96C78—H78A0.98
C19—C201.504 (9)C78—H78B0.96
C19—H190.98C78—H78C0.97
C20—H20A0.98C79—H79A0.99
C20—H20B0.96C79—H79B0.97
C21—C221.50 (1)C79—H79C0.97
C21—H21A0.96C80—C811.540 (8)
C21—H21B0.96C80—C821.518 (8)
C22—C231.36 (1)C80—C831.572 (8)
C22—C271.37 (1)C81—H81A0.96
C23—C241.38 (2)C81—H81B0.96
C23—H230.99C81—H81C0.96
C24—C251.34 (2)C82—H82A0.97
C24—H241.026C82—H82B0.97
C25—C261.35 (3)C82—H82C0.98
C25—H251.01C83—C841.529 (8)
C26—C271.40 (2)C83—H830.98
C26—H260.98C84—C851.496 (9)
C27—H270.98C84—H84A0.95
C28—H28A0.97C84—H84B0.99
C28—H28B0.95C85—H85A0.95
C28—H28C0.95C85—H85B0.98
C29—H29A0.97C86—H86A0.98
C29—H29B0.95C86—H86B0.94
C29—H29C0.98C86—H86C0.96
C30—C311.543 (8)C87—H87A0.92
C30—C321.540 (8)C87—H87B0.97
C30—C331.582 (8)C87—H87C1.00
C31—H31A0.95C88—C891.55 (1)
C31—H31B0.96C88—C901.57 (1)
C31—H31C0.97C88—C911.58 (1)
C32—H32A0.98C89—H89A0.93
C32—H32B0.94C89—H89B0.96
C32—H32C0.97C89—H89C1.01
C33—C341.526 (8)C90—H90A0.98
C33—H330.98C90—H90B0.98
C34—C351.505 (9)C90—H90C0.96
C34—H34A0.97C91—H91A0.92
C34—H34B0.96C91—H91B0.97
C35—H35A0.97C91—H91C0.99
C10—S1—C13103.5 (3)H39A—C39—H39C106
C12—S2—C13103.2 (3)H39B—C39—H39C107
C60—S51—C63104.8 (3)C38—C40—H40A113
C62—S52—C63102.7 (3)C38—C40—H40B113
O8—Si3—C36113.7 (3)C38—C40—H40C111
O8—Si3—C37113.3 (4)H40A—C40—H40B108
O8—Si3—C38103.8 (3)H40A—C40—H40C105
C36—Si3—C37105.5 (4)H40B—C40—H40C105
C36—Si3—C38111.1 (4)C38—C41—H41A109
C37—Si3—C38109.5 (4)C38—C41—H41B114
O58—Si53—C86115.4 (3)C38—C41—H41C109
O58—Si53—C87114.4 (4)H41A—C41—H41B109
O58—Si53—C88101.9 (3)H41A—C41—H41C105
C86—Si53—C87104.1 (4)H41B—C41—H41C109
C86—Si53—C88111.2 (4)S51—C60—C61113.7 (5)
C87—Si53—C88110.1 (4)S51—C60—H60A109
C15—O4—C19111.2 (4)S51—C60—H60B108
C17—O5—C28115.8 (6)C61—C60—H60A108
C17—O6—C29115.2 (6)C61—C60—H60B109
C20—O7—C21112.8 (5)H60A—C60—H60B109
Si3—O8—C33128.8 (4)C60—C61—C62113.6 (6)
C35—O9—H9103 (3)C60—C61—H61A110
C65—O54—C69112.9 (4)C60—C61—H61B108
C67—O55—C78115.6 (5)C62—C61—H61A110
C67—O56—C79117.1 (5)C62—C61—H61B108
C70—O57—C71114.7 (6)H61A—C61—H61B107
Si53—O58—C83128.8 (4)S52—C62—C61114.5 (5)
C85—O59—H59109 (3)S52—C62—H62A108
S1—C10—C11115.0 (5)S52—C62—H62B108
S1—C10—H10A109C61—C62—H62A109
S1—C10—H10B109C61—C62—H62B108
C11—C10—H10A108H62A—C62—H62B109
C11—C10—H10B108S51—C63—S52109.7 (3)
H10A—C10—H10B109S51—C63—C64105.6 (3)
C10—C11—C12113.4 (6)S51—C63—C80106.9 (3)
C10—C11—H11A111S52—C63—C64108.4 (4)
C10—C11—H11B109S52—C63—C80110.7 (3)
C12—C11—H11A109C64—C63—C80115.2 (4)
C12—C11—H11B107C63—C64—C65120.6 (4)
H11A—C11—H11B108C63—C64—H64A107
S2—C12—C11113.8 (5)C63—C64—H64B107
S2—C12—H12A109C65—C64—H64A107
S2—C12—H12B109C65—C64—H64B107
C11—C12—H12A109H64A—C64—H64B109
C11—C12—H12B108O54—C65—C64109.7 (4)
H12A—C12—H12B108O54—C65—C66108.7 (4)
S1—C13—S2109.6 (3)O54—C65—H65109
S1—C13—C14106.1 (3)C64—C65—C66110.0 (4)
S1—C13—C30106.8 (4)C64—C65—H65110
S2—C13—C14109.1 (4)C66—C65—H65110
S2—C13—C30109.6 (4)C65—C66—C67113.4 (5)
C14—C13—C30115.6 (4)C65—C66—H66A108
C13—C14—C15120.1 (5)C65—C66—H66B108
C13—C14—H14A107C67—C66—H66A111
C13—C14—H14B106C67—C66—H66B110
C15—C14—H14A108H66A—C66—H66B107
C15—C14—H14B107O55—C67—O56110.4 (5)
H14A—C14—H14B109O55—C67—C66105.2 (5)
O4—C15—C14109.4 (4)O55—C67—C68113.2 (5)
O4—C15—C16107.8 (5)O56—C67—C66112.1 (5)
O4—C15—H15109O56—C67—C68105.6 (5)
C14—C15—C16111.8 (5)C66—C67—C68110.5 (5)
C14—C15—H15110C67—C68—C69112.8 (5)
C16—C15—H15110C67—C68—H68A109
C15—C16—C17111.2 (5)C67—C68—H68B110
C15—C16—H16A110C69—C68—H68A107
C15—C16—H16B109C69—C68—H68B109
C17—C16—H16A111H68A—C68—H68B110
C17—C16—H16B109O54—C69—C68109.3 (4)
H16A—C16—H16B107O54—C69—C70107.3 (4)
O5—C17—O6109.9 (5)O54—C69—H69108
O5—C17—C16112.1 (5)C68—C69—C70113.2 (5)
O5—C17—C18105.2 (5)C68—C69—H69109
O6—C17—C16104.7 (5)C70—C69—H69110
O6—C17—C18113.5 (5)O57—C70—C69108.5 (5)
C16—C17—C18111.6 (5)O57—C70—H70A110
C17—C18—C19111.4 (5)O57—C70—H70B110
C17—C18—H18A109C69—C70—H70A111
C17—C18—H18B110C69—C70—H70B110
C19—C18—H18A108H70A—C70—H70B108
C19—C18—H18B109O57—C71—C72113.8 (6)
H18A—C18—H18B109O57—C71—H71A109
O4—C19—C18110.5 (5)O57—C71—H71B108
O4—C19—C20107.7 (5)C72—C71—H71A108
O4—C19—H19108C72—C71—H71B108
C18—C19—C20113.2 (5)H71A—C71—H71B109
C18—C19—H19108C71—C72—C73121.0 (8)
C20—C19—H19109C71—C72—C77120.2 (8)
O7—C20—C19108.3 (5)C73—C72—C77118.8 (8)
O7—C20—H20A110C72—C73—C74121 (1)
O7—C20—H20B111C72—C73—H73117
C19—C20—H20A109C74—C73—H73121
C19—C20—H20B110C73—C74—C75119 (1)
H20A—C20—H20B108C73—C74—H74116
O7—C21—C22113.4 (6)C75—C74—H74124
O7—C21—H21A108C74—C75—C76122 (1)
O7—C21—H21B109C74—C75—H75119
C22—C21—H21A108C76—C75—H75117
C22—C21—H21B109C75—C76—C77117 (1)
H21A—C21—H21B109C75—C76—H76123
C21—C22—C23121.2 (7)C77—C76—H76118
C21—C22—C27119.9 (8)C72—C77—C76120 (1)
C23—C22—C27118.8 (7)C72—C77—H77117
C22—C23—C24120.5 (9)C76—C77—H77121
C22—C23—H23118O55—C78—H78A110
C24—C23—H23121O55—C78—H78B112
C23—C24—C25121 (1)O55—C78—H78C111
C23—C24—H24117H78A—C78—H78B108
C25—C24—H24121H78A—C78—H78C107
C24—C25—C26119 (1)H78B—C78—H78C109
C24—C25—H25117O56—C79—H79A111
C26—C25—H25123O56—C79—H79B112
C25—C26—C27120 (1)O56—C79—H79C112
C25—C26—H26121H79A—C79—H79B107
C27—C26—H26117H79A—C79—H79C107
C22—C27—C26119 (1)H79B—C79—H79C108
C22—C27—H27119C63—C80—C81108.2 (4)
C26—C27—H27122C63—C80—C82110.7 (4)
O5—C28—H28A109C63—C80—C83112.8 (4)
O5—C28—H28B109C81—C80—C82108.5 (5)
O5—C28—H28C110C81—C80—C83107.5 (5)
H28A—C28—H28B109C82—C80—C83109.0 (5)
H28A—C28—H28C109C80—C81—H81A110
H28B—C28—H28C111C80—C81—H81B109
O6—C29—H29A112C80—C81—H81C109
O6—C29—H29B111H81A—C81—H81B110
O6—C29—H29C110H81A—C81—H81C110
H29A—C29—H29B110H81B—C81—H81C110
H29A—C29—H29C107C80—C82—H82A111
H29B—C29—H29C108C80—C82—H82B111
C13—C30—C31108.0 (4)C80—C82—H82C111
C13—C30—C32111.7 (4)H82A—C82—H82B109
C13—C30—C33113.4 (4)H82A—C82—H82C108
C31—C30—C32107.0 (5)H82B—C82—H82C108
C31—C30—C33107.0 (5)O58—C83—C80107.7 (4)
C32—C30—C33109.4 (5)O58—C83—C84108.8 (4)
C30—C31—H31A111O58—C83—H83108
C30—C31—H31B109C80—C83—C84116.5 (5)
C30—C31—H31C109C80—C83—H83108
H31A—C31—H31B110C84—C83—H83108
H31A—C31—H31C109C83—C84—C85112.8 (5)
H31B—C31—H31C109C83—C84—H84A110
C30—C32—H32A109C83—C84—H84B109
C30—C32—H32B111C85—C84—H84A109
C30—C32—H32C110C85—C84—H84B108
H32A—C32—H32B109H84A—C84—H84B108
H32A—C32—H32C107O59—C85—C84110.5 (5)
H32B—C32—H32C110O59—C85—H85A110
O8—C33—C30108.6 (4)O59—C85—H85B109
O8—C33—C34108.3 (4)C84—C85—H85A110
O8—C33—H33108C84—C85—H85B109
C30—C33—C34114.9 (5)H85A—C85—H85B109
C30—C33—H33109Si53—C86—H86A109
C34—C33—H33108Si53—C86—H86B110
C33—C34—C35112.8 (5)Si53—C86—H86C109
C33—C34—H34A109H86A—C86—H86B109
C33—C34—H34B110H86A—C86—H86C108
C35—C34—H34A108H86B—C86—H86C111
C35—C34—H34B109Si53—C87—H87A113
H34A—C34—H34B108Si53—C87—H87B110
O9—C35—C34109.7 (5)Si53—C87—H87C108
O9—C35—H35A109H87A—C87—H87B111
O9—C35—H35B110H87A—C87—H87C109
C34—C35—H35A110H87B—C87—H87C105
C34—C35—H35B110Si53—C88—C89108.7 (6)
H35A—C35—H35B108Si53—C88—C90108.7 (5)
Si3—C36—H36A110Si53—C88—C91108.6 (6)
Si3—C36—H36B109C89—C88—C90109.6 (8)
Si3—C36—H36C110C89—C88—C91111.5 (8)
H36A—C36—H36B109C90—C88—C91109.7 (8)
H36A—C36—H36C110C88—C89—H89A112
H36B—C36—H36C109C88—C89—H89B111
Si3—C37—H37A112C88—C89—H89C109
Si3—C37—H37B111H89A—C89—H89B111
Si3—C37—H37C110H89A—C89—H89C108
H37A—C37—H37B108H89B—C89—H89C106
H37A—C37—H37C108C88—C90—H90A111
H37B—C37—H37C107C88—C90—H90B111
Si3—C38—C39110.8 (7)C88—C90—H90C114
Si3—C38—C40109.9 (6)H90A—C90—H90B106
Si3—C38—C41110.1 (6)H90A—C90—H90C108
C39—C38—C40107.9 (8)H90B—C90—H90C108
C39—C38—C41108.6 (8)C88—C91—H91A111
C40—C38—C41109.5 (8)C88—C91—H91B109
C38—C39—H39A110C88—C91—H91C107
C38—C39—H39B112H91A—C91—H91B111
C38—C39—H39C109H91A—C91—H91C110
H39A—C39—H39B110H91B—C91—H91C106
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9···O4i0.97 (5)2.17 (6)3.035 (6)147 (5)
O9—H9···O7i0.97 (5)2.41 (4)3.188 (7)136 (5)
O59—H59···O54ii0.98 (5)2.30 (6)3.096 (6)138 (5)
O59—H59···O57ii0.98 (5)2.28 (5)3.082 (7)139 (5)
Symmetry codes: (i) x, y+1/2, z+2; (ii) x1, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC32H56O6S2Si
Mr629.00
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)6.878 (3), 19.658 (3), 26.493 (2)
β (°) 91.33 (2)
V3)3581.1 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.7 × 0.6 × 0.1
Data collection
DiffractometerRigaku AFC5
diffractometer
Absorption correctionIntegration
(Coppens et al., 1965)
Tmin, Tmax0.881, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
7078, 6497, 4622
Rint0.030
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.130, 1.02
No. of reflections6497
No. of parameters745
No. of restraints?
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.00, 0.29
Absolute structureFlack (1983), no Friedel pairs
Absolute structure parameter0.0 (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.

Selected geometric parameters (Å, º) top
S1—C101.805 (7)Si3—O81.648 (4)
S1—C131.859 (5)Si3—C361.856 (8)
S2—C121.807 (7)Si3—C371.864 (10)
S2—C131.843 (6)Si3—C381.878 (8)
S51—C601.807 (7)Si53—O581.663 (5)
S51—C631.861 (5)Si53—C861.845 (8)
S52—C621.829 (7)Si53—C871.853 (9)
S52—C631.836 (5)Si53—C881.876 (8)
Si3—O8—C33128.8 (4)Si53—O58—C83128.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9···O4i0.97 (5)2.17 (6)3.035 (6)147 (5)
O9—H9···O7i0.97 (5)2.41 (4)3.188 (7)136 (5)
O59—H59···O54ii0.98 (5)2.30 (6)3.096 (6)138 (5)
O59—H59···O57ii0.98 (5)2.28 (5)3.082 (7)139 (5)
Symmetry codes: (i) x, y+1/2, z+2; (ii) x1, y+1/2, z+1.
 

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