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Two hydrogen-bonded, well defined compounds were synthesized from tris­(2,6-diisopropyl)phenoxysilanethiol (TDST) and triethylamine (TDST–TEA) or pyridine (TDST–py). The crystalline compounds were characterized in the solid state by variable-temperature X-ray diffraction measurements and ATR FT–IR spectroscopy. The toluene solutions of TDST–TEA and TDST–py were studied by NMR spectroscopy. The total hydrogen-bond energies and FT–IR spectra were calculated with the use of BLYP-D/TZP and B3LYP/6-31G(d,p)/GD3BJ methods. Thermochemical parameters and potential energy scans were calculated at the B3LYP/6-31G(d,p)/GD3BJ level. All results point to the higher energy of bonding in TDST–TEA both in the solid state and in solution. At the same time the potential energy scan reveals a very broad double-well hydrogen bond in TDST-py, indicating good stabilization of the system for a wide range of D—H...A distances.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616011562/eb5051sup1.cif
Contains datablocks global, tdst_et3n_90, tdst_et3n_120, tdst_et3n_150, tdst_et3n_165, tdst_et3n_180, tdst_et3n_210, tdst_et3n_temp_240, tdst_py_temp_90, tdst_py_120, tdst_py_150, tdst_py_180k, tdst_py_210, tdst_py_240, tdst_py_270

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_90sup2.hkl
Contains datablock tdst_et3n_90

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_120sup3.hkl
Contains datablock tdst_et3n_120

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_150sup4.hkl
Contains datablock tdst_et3n_150

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_165sup5.hkl
Contains datablock tdst_et3n_165

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_180sup6.hkl
Contains datablock tdst_et3n_180

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_210sup7.hkl
Contains datablock tdst_et3n_210

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_temp_240sup8.hkl
Contains datablock tdst_et3n_temp_240

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_temp_90sup9.hkl
Contains datablock tdst_py_temp_90

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_120sup10.hkl
Contains datablock tdst_py_120

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_150sup11.hkl
Contains datablock tdst_py_150

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_180ksup12.hkl
Contains datablock tdst_py_180k

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_210sup13.hkl
Contains datablock tdst_py_210

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_240sup14.hkl
Contains datablock tdst_py_240

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_270sup15.hkl
Contains datablock tdst_py_270

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520616011562/eb5051sup16.pdf
Supporting figues and tables

CCDC references: 1493986; 1493987; 1493988; 1493989; 1493990; 1493991; 1493992; 1493993; 1493994; 1493995; 1493996; 1493997; 1493998; 1493999

Computing details top

For all compounds, data collection: STOE X-AREA; cell refinement: STOE X-AREA; data reduction: STOE X-RED; program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014).

(tdst_et3n_90) top
Crystal data top
C42H67NO3SSiF(000) = 1520
Mr = 694.11Dx = 1.123 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1642 reflections
a = 11.6341 (17) Åθ = 3.4–29.4°
b = 17.8996 (16) ŵ = 0.15 mm1
c = 20.096 (3) ÅT = 90 K
β = 101.098 (12)°Block, colourless
V = 4106.7 (9) Å30.34 × 0.22 × 0.13 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
5341 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.084
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.1°
rotation method scansh = 1413
13602 measured reflectionsk = 2222
7538 independent reflectionsl = 2424
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0406P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105(Δ/σ)max < 0.001
S = 0.88Δρmax = 0.33 e Å3
7538 reflectionsΔρmin = 0.25 e Å3
452 parametersAbsolute structure: Flack x determined using 1785 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 0.03 (11)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.55624 (10)0.26080 (7)0.06091 (7)0.0109 (3)
S1140.40718 (10)0.20800 (7)0.01637 (7)0.0156 (3)
O1120.5472 (3)0.35280 (17)0.05841 (17)0.0135 (7)
O1100.5925 (3)0.23785 (18)0.14274 (16)0.0139 (7)
O1110.6746 (3)0.24698 (18)0.02831 (16)0.0138 (7)
N1090.1974 (3)0.2845 (2)0.0753 (2)0.0168 (9)
H1150.280 (5)0.271 (3)0.049 (3)0.035 (17)*
C380.7322 (4)0.1431 (3)0.0344 (2)0.0143 (10)
C780.5840 (4)0.3837 (3)0.0782 (3)0.0171 (11)
H790.53790.3430.0640.02*
C10.5327 (4)0.1953 (3)0.1825 (2)0.0142 (10)
C50.4228 (4)0.1103 (3)0.2679 (2)0.0175 (11)
H60.38570.08170.29620.021*
C310.8584 (4)0.1882 (3)0.0700 (2)0.0143 (10)
C20.4377 (4)0.2260 (3)0.2066 (2)0.0144 (10)
C390.8832 (4)0.2455 (3)0.1280 (2)0.0156 (10)
H400.80850.2580.14090.019*
C450.9330 (4)0.3174 (3)0.1022 (3)0.0213 (12)
H461.00650.30650.08920.032*
H470.94480.35420.13760.032*
H480.87890.33630.06380.032*
C100.3943 (4)0.3050 (3)0.1915 (2)0.0158 (11)
H110.43260.32480.15580.019*
C410.9653 (4)0.2154 (3)0.1908 (3)0.0222 (12)
H420.93670.16810.20320.033*
H430.96840.250.22760.033*
H441.04240.20910.18110.033*
C220.6274 (5)0.0514 (3)0.1047 (3)0.0232 (12)
H230.58430.00760.11240.035*
H240.69160.03740.08360.035*
H250.57680.08510.07550.035*
C340.9232 (4)0.0865 (3)0.0073 (3)0.0210 (12)
H350.97940.0510.00240.025*
C200.6745 (4)0.0899 (3)0.1722 (3)0.0151 (10)
H210.72430.13140.16320.018*
C30.3839 (4)0.1815 (3)0.2494 (2)0.0167 (11)
H40.32020.20060.26560.02*
C840.4998 (5)0.4393 (3)0.1200 (3)0.0244 (12)
H850.54310.48140.13170.037*
H860.44360.4560.09390.037*
H870.45970.41540.16070.037*
C950.1071 (4)0.2506 (3)0.0396 (3)0.0195 (11)
H960.12640.2640.0080.023*
H970.11160.19670.04260.023*
C300.7529 (4)0.1911 (3)0.0219 (2)0.0134 (10)
C610.7660 (4)0.5021 (3)0.0976 (3)0.0212 (12)
H620.80370.52930.13480.025*
C320.9410 (4)0.1358 (3)0.0619 (3)0.0197 (11)
H331.01040.13320.09370.024*
C680.6605 (4)0.4337 (3)0.1774 (2)0.0161 (11)
H690.60720.3910.1750.019*
C700.7713 (5)0.4154 (3)0.2297 (3)0.0220 (12)
H710.80720.37120.21590.033*
H720.75090.40710.27320.033*
H730.82530.45640.23280.033*
C1050.2222 (5)0.3985 (3)0.0029 (3)0.0265 (13)
H1060.22980.45190.00430.04*
H1070.2930.37740.02250.04*
H1080.15770.38590.01850.04*
C90.5741 (4)0.1226 (3)0.2008 (2)0.0140 (10)
C910.2930 (5)0.2676 (3)0.1766 (3)0.0267 (13)
H920.28350.24270.21960.04*
H930.36120.24850.14690.04*
H940.30190.32030.18290.04*
C160.2618 (4)0.3091 (3)0.1655 (3)0.0208 (12)
H170.24010.27540.1280.031*
H180.24040.35910.15110.031*
H190.22190.29520.20130.031*
C600.6863 (4)0.4466 (3)0.1070 (3)0.0172 (11)
C360.8195 (4)0.0918 (3)0.0397 (3)0.0188 (11)
H370.80770.05950.07660.023*
C880.1862 (4)0.2538 (3)0.1457 (3)0.0199 (11)
H890.11850.27640.17440.024*
H900.17230.20050.14460.024*
C120.4301 (4)0.3547 (3)0.2547 (3)0.0185 (11)
H130.39750.33480.29130.028*
H140.4010.40450.24460.028*
H150.51390.3560.26750.028*
C650.7323 (4)0.4777 (3)0.0212 (3)0.0205 (12)
H660.7480.48830.06390.025*
C800.6655 (5)0.3508 (3)0.1219 (3)0.0255 (13)
H810.61970.32710.1610.038*
H820.71630.31460.0960.038*
H830.71160.390.13610.038*
C980.0176 (4)0.2747 (3)0.0676 (3)0.0247 (12)
H990.03560.26560.11560.037*
H1000.02590.3270.05920.037*
H1010.07040.24670.04590.037*
C1670.6512 (4)0.4221 (3)0.0151 (2)0.0159 (11)
C590.6306 (4)0.4062 (3)0.0502 (3)0.0133 (10)
C260.7512 (5)0.0359 (3)0.2201 (3)0.0262 (13)
H270.70860.00950.22340.039*
H280.77240.05820.26420.039*
H290.82070.02490.20280.039*
C70.5177 (4)0.0821 (3)0.2440 (2)0.0160 (11)
H80.54460.03440.25720.019*
C740.5977 (5)0.5026 (3)0.1994 (3)0.0268 (13)
H750.57910.49370.24330.04*
H760.52680.51160.16710.04*
H770.6480.54540.20160.04*
C630.7901 (5)0.5176 (3)0.0344 (3)0.0222 (12)
H640.84450.55420.02920.027*
C1020.2000 (5)0.3678 (3)0.0743 (3)0.0188 (11)
H1030.12580.38680.09890.023*
H1040.26110.38520.09730.023*
C490.6212 (4)0.1456 (3)0.0887 (3)0.0173 (11)
H500.57590.18960.08030.021*
C550.5442 (5)0.0765 (3)0.0872 (3)0.0222 (12)
H560.58640.03280.09610.033*
H570.47430.08130.12120.033*
H580.52360.07220.04330.033*
C510.6506 (5)0.1535 (3)0.1600 (3)0.0239 (12)
H520.69960.19640.16110.036*
H530.57940.15940.19290.036*
H540.69090.10950.17050.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0101 (6)0.0125 (7)0.0098 (7)0.0003 (6)0.0012 (5)0.0000 (6)
S1140.0122 (6)0.0158 (6)0.0169 (7)0.0023 (5)0.0022 (5)0.0001 (5)
O1120.0111 (16)0.0179 (18)0.0112 (17)0.0007 (15)0.0015 (13)0.0005 (15)
O1100.0148 (16)0.0166 (18)0.0105 (17)0.0031 (14)0.0032 (13)0.0030 (14)
O1110.0132 (16)0.0160 (18)0.0125 (17)0.0028 (13)0.0028 (13)0.0005 (14)
N1090.014 (2)0.022 (2)0.013 (2)0.0006 (18)0.0002 (17)0.0007 (18)
C380.015 (2)0.013 (3)0.014 (3)0.002 (2)0.001 (2)0.001 (2)
C780.021 (3)0.015 (3)0.014 (3)0.002 (2)0.002 (2)0.002 (2)
C10.016 (2)0.015 (3)0.010 (2)0.0069 (19)0.0011 (19)0.001 (2)
C50.023 (3)0.019 (3)0.011 (3)0.010 (2)0.004 (2)0.000 (2)
C310.014 (2)0.013 (2)0.015 (3)0.0010 (19)0.0019 (19)0.001 (2)
C20.013 (2)0.017 (3)0.010 (2)0.0046 (19)0.0047 (19)0.001 (2)
C390.015 (2)0.016 (3)0.015 (2)0.001 (2)0.0001 (19)0.001 (2)
C450.017 (3)0.025 (3)0.021 (3)0.001 (2)0.002 (2)0.007 (2)
C100.016 (2)0.022 (3)0.011 (2)0.004 (2)0.0051 (19)0.003 (2)
C410.023 (3)0.031 (3)0.012 (3)0.002 (2)0.000 (2)0.003 (2)
C220.024 (3)0.021 (3)0.025 (3)0.005 (2)0.005 (2)0.001 (2)
C340.019 (3)0.015 (3)0.029 (3)0.007 (2)0.003 (2)0.001 (2)
C200.016 (2)0.009 (2)0.021 (3)0.0012 (19)0.005 (2)0.001 (2)
C30.014 (2)0.023 (3)0.013 (3)0.003 (2)0.004 (2)0.004 (2)
C840.025 (3)0.021 (3)0.025 (3)0.003 (2)0.003 (2)0.003 (2)
C950.020 (3)0.022 (3)0.016 (3)0.001 (2)0.001 (2)0.003 (2)
C300.012 (2)0.014 (3)0.014 (3)0.0011 (19)0.0035 (19)0.006 (2)
C610.023 (3)0.022 (3)0.015 (3)0.007 (2)0.005 (2)0.004 (2)
C320.019 (3)0.020 (3)0.018 (3)0.004 (2)0.001 (2)0.002 (2)
C680.018 (3)0.016 (3)0.014 (3)0.003 (2)0.002 (2)0.003 (2)
C700.028 (3)0.023 (3)0.014 (3)0.000 (2)0.002 (2)0.002 (2)
C1050.040 (3)0.016 (3)0.023 (3)0.001 (2)0.004 (3)0.001 (2)
C90.013 (2)0.016 (3)0.011 (3)0.0002 (19)0.0037 (19)0.003 (2)
C910.031 (3)0.033 (3)0.016 (3)0.002 (3)0.005 (2)0.006 (2)
C160.018 (3)0.028 (3)0.015 (3)0.004 (2)0.001 (2)0.001 (2)
C600.020 (3)0.017 (3)0.013 (3)0.001 (2)0.001 (2)0.001 (2)
C360.020 (3)0.020 (3)0.016 (3)0.003 (2)0.003 (2)0.005 (2)
C880.024 (3)0.021 (3)0.015 (3)0.003 (2)0.005 (2)0.002 (2)
C120.018 (3)0.017 (3)0.019 (3)0.003 (2)0.000 (2)0.002 (2)
C650.023 (3)0.021 (3)0.017 (3)0.002 (2)0.004 (2)0.004 (2)
C800.024 (3)0.032 (3)0.019 (3)0.001 (2)0.002 (2)0.007 (2)
C980.019 (3)0.037 (3)0.019 (3)0.002 (2)0.005 (2)0.004 (3)
C1670.013 (2)0.018 (3)0.016 (3)0.001 (2)0.000 (2)0.005 (2)
C590.011 (2)0.010 (2)0.018 (3)0.0000 (19)0.001 (2)0.000 (2)
C260.024 (3)0.029 (3)0.024 (3)0.008 (2)0.001 (2)0.004 (3)
C70.023 (3)0.010 (3)0.014 (3)0.002 (2)0.001 (2)0.000 (2)
C740.033 (3)0.030 (3)0.019 (3)0.004 (2)0.010 (3)0.002 (3)
C630.023 (3)0.017 (3)0.026 (3)0.008 (2)0.003 (2)0.002 (2)
C1020.027 (3)0.016 (3)0.015 (3)0.002 (2)0.006 (2)0.002 (2)
C490.017 (3)0.019 (3)0.016 (3)0.006 (2)0.001 (2)0.004 (2)
C550.025 (3)0.023 (3)0.016 (3)0.001 (2)0.001 (2)0.004 (2)
C510.029 (3)0.026 (3)0.017 (3)0.008 (2)0.005 (2)0.000 (2)
Geometric parameters (Å, º) top
Si1—O1121.650 (3)C61—C601.395 (7)
Si1—O1111.654 (3)C61—H620.93
Si1—O1101.669 (3)C32—H330.93
Si1—S1142.0258 (18)C68—C601.520 (7)
O112—C591.394 (6)C68—C701.534 (7)
O110—C11.383 (6)C68—C741.541 (7)
O111—C301.376 (6)C68—H690.98
N109—C1021.492 (7)C70—H710.96
N109—C881.498 (6)C70—H720.96
N109—C951.509 (6)C70—H730.96
N109—H1151.03 (6)C105—C1021.511 (7)
C38—C361.387 (7)C105—H1060.96
C38—C301.403 (7)C105—H1070.96
C38—C491.523 (7)C105—H1080.96
C78—C1671.519 (7)C9—C71.389 (7)
C78—C801.529 (7)C91—C881.513 (7)
C78—C841.530 (7)C91—H920.96
C78—H790.98C91—H930.96
C1—C21.401 (7)C91—H940.96
C1—C91.412 (7)C16—H170.96
C5—C31.380 (7)C16—H180.96
C5—C71.382 (7)C16—H190.96
C5—H60.93C60—C591.402 (7)
C31—C321.374 (7)C36—H370.93
C31—C301.410 (6)C88—H890.97
C31—C391.538 (7)C88—H900.97
C2—C31.404 (7)C12—H130.96
C2—C101.513 (7)C12—H140.96
C39—C411.527 (7)C12—H150.96
C39—C451.542 (7)C65—C631.387 (7)
C39—H400.98C65—C1671.392 (7)
C45—H460.96C65—H660.93
C45—H470.96C80—H810.96
C45—H480.96C80—H820.96
C10—C161.531 (6)C80—H830.96
C10—C121.542 (7)C98—H990.96
C10—H110.98C98—H1000.96
C41—H420.96C98—H1010.96
C41—H430.96C167—C591.407 (7)
C41—H440.96C26—H270.96
C22—C201.526 (7)C26—H280.96
C22—H230.96C26—H290.96
C22—H240.96C7—H80.93
C22—H250.96C74—H750.96
C34—C361.384 (7)C74—H760.96
C34—C321.392 (7)C74—H770.96
C34—H350.93C63—H640.93
C20—C91.516 (6)C102—H1030.97
C20—C261.526 (7)C102—H1040.97
C20—H210.98C49—C551.531 (7)
C3—H40.93C49—C511.542 (7)
C84—H850.96C49—H500.98
C84—H860.96C55—H560.96
C84—H870.96C55—H570.96
C95—C981.514 (7)C55—H580.96
C95—H960.97C51—H520.96
C95—H970.97C51—H530.96
C61—C631.381 (7)C51—H540.96
O112—Si1—O111100.97 (17)H71—C70—H72109.5
O112—Si1—O110106.15 (18)C68—C70—H73109.5
O111—Si1—O110106.38 (16)H71—C70—H73109.5
O112—Si1—S114114.07 (14)H72—C70—H73109.5
O111—Si1—S114117.56 (13)C102—C105—H106109.5
O110—Si1—S114110.67 (12)C102—C105—H107109.5
C59—O112—Si1130.2 (3)H106—C105—H107109.5
C1—O110—Si1130.1 (3)C102—C105—H108109.5
C30—O111—Si1139.7 (3)H106—C105—H108109.5
C102—N109—C88112.1 (4)H107—C105—H108109.5
C102—N109—C95114.1 (4)C7—C9—C1117.8 (4)
C88—N109—C95111.1 (4)C7—C9—C20121.8 (4)
C102—N109—H115102 (3)C1—C9—C20120.4 (4)
C88—N109—H115108 (3)C88—C91—H92109.5
C95—N109—H115109 (3)C88—C91—H93109.5
C36—C38—C30116.9 (4)H92—C91—H93109.5
C36—C38—C49119.8 (4)C88—C91—H94109.5
C30—C38—C49123.3 (4)H92—C91—H94109.5
C167—C78—C80112.2 (4)H93—C91—H94109.5
C167—C78—C84109.7 (4)C10—C16—H17109.5
C80—C78—C84109.7 (4)C10—C16—H18109.5
C167—C78—H79108.4H17—C16—H18109.5
C80—C78—H79108.4C10—C16—H19109.5
C84—C78—H79108.4H17—C16—H19109.5
O110—C1—C2120.2 (4)H18—C16—H19109.5
O110—C1—C9118.3 (4)C61—C60—C59118.2 (5)
C2—C1—C9121.5 (4)C61—C60—C68119.3 (4)
C3—C5—C7119.1 (5)C59—C60—C68122.5 (4)
C3—C5—H6120.4C34—C36—C38123.2 (5)
C7—C5—H6120.4C34—C36—H37118.4
C32—C31—C30118.7 (5)C38—C36—H37118.4
C32—C31—C39120.8 (4)N109—C88—C91113.5 (4)
C30—C31—C39120.5 (4)N109—C88—H89108.9
C1—C2—C3117.7 (4)C91—C88—H89108.9
C1—C2—C10123.4 (4)N109—C88—H90108.9
C3—C2—C10118.8 (4)C91—C88—H90108.9
C41—C39—C31112.8 (4)H89—C88—H90107.7
C41—C39—C45110.9 (4)C10—C12—H13109.5
C31—C39—C45109.3 (4)C10—C12—H14109.5
C41—C39—H40107.9H13—C12—H14109.5
C31—C39—H40107.9C10—C12—H15109.5
C45—C39—H40107.9H13—C12—H15109.5
C39—C45—H46109.5H14—C12—H15109.5
C39—C45—H47109.5C63—C65—C167121.9 (5)
H46—C45—H47109.5C63—C65—H66119.1
C39—C45—H48109.5C167—C65—H66119.1
H46—C45—H48109.5C78—C80—H81109.5
H47—C45—H48109.5C78—C80—H82109.5
C2—C10—C16112.9 (4)H81—C80—H82109.5
C2—C10—C12110.4 (4)C78—C80—H83109.5
C16—C10—C12110.3 (4)H81—C80—H83109.5
C2—C10—H11107.7H82—C80—H83109.5
C16—C10—H11107.7C95—C98—H99109.5
C12—C10—H11107.7C95—C98—H100109.5
C39—C41—H42109.5H99—C98—H100109.5
C39—C41—H43109.5C95—C98—H101109.5
H42—C41—H43109.5H99—C98—H101109.5
C39—C41—H44109.5H100—C98—H101109.5
H42—C41—H44109.5C65—C167—C59117.9 (4)
H43—C41—H44109.5C65—C167—C78119.8 (5)
C20—C22—H23109.5C59—C167—C78122.3 (4)
C20—C22—H24109.5O112—C59—C60118.7 (4)
H23—C22—H24109.5O112—C59—C167119.8 (4)
C20—C22—H25109.5C60—C59—C167121.3 (4)
H23—C22—H25109.5C20—C26—H27109.5
H24—C22—H25109.5C20—C26—H28109.5
C36—C34—C32118.1 (5)H27—C26—H28109.5
C36—C34—H35120.9C20—C26—H29109.5
C32—C34—H35120.9H27—C26—H29109.5
C9—C20—C26113.9 (4)H28—C26—H29109.5
C9—C20—C22109.9 (4)C5—C7—C9122.1 (5)
C26—C20—C22109.9 (4)C5—C7—H8119
C9—C20—H21107.6C9—C7—H8119
C26—C20—H21107.6C68—C74—H75109.5
C22—C20—H21107.6C68—C74—H76109.5
C5—C3—C2121.8 (5)H75—C74—H76109.5
C5—C3—H4119.1C68—C74—H77109.5
C2—C3—H4119.1H75—C74—H77109.5
C78—C84—H85109.5H76—C74—H77109.5
C78—C84—H86109.5C61—C63—C65119.0 (5)
H85—C84—H86109.5C61—C63—H64120.5
C78—C84—H87109.5C65—C63—H64120.5
H85—C84—H87109.5N109—C102—C105112.1 (4)
H86—C84—H87109.5N109—C102—H103109.2
N109—C95—C98114.5 (4)C105—C102—H103109.2
N109—C95—H96108.6N109—C102—H104109.2
C98—C95—H96108.6C105—C102—H104109.2
N109—C95—H97108.6H103—C102—H104107.9
C98—C95—H97108.6C38—C49—C55112.3 (4)
H96—C95—H97107.6C38—C49—C51111.1 (4)
O111—C30—C38120.5 (4)C55—C49—C51109.1 (4)
O111—C30—C31117.8 (4)C38—C49—H50108.1
C38—C30—C31121.4 (4)C55—C49—H50108.1
C63—C61—C60121.7 (5)C51—C49—H50108.1
C63—C61—H62119.1C49—C55—H56109.5
C60—C61—H62119.1C49—C55—H57109.5
C31—C32—C34121.7 (5)H56—C55—H57109.5
C31—C32—H33119.2C49—C55—H58109.5
C34—C32—H33119.2H56—C55—H58109.5
C60—C68—C70112.3 (4)H57—C55—H58109.5
C60—C68—C74109.6 (4)C49—C51—H52109.5
C70—C68—C74110.9 (4)C49—C51—H53109.5
C60—C68—H69108H52—C51—H53109.5
C70—C68—H69108C49—C51—H54109.5
C74—C68—H69108H52—C51—H54109.5
C68—C70—H71109.5H53—C51—H54109.5
C68—C70—H72109.5
O111—Si1—O112—C5916.4 (4)C2—C1—C9—C20178.0 (4)
O110—Si1—O112—C5994.4 (4)C26—C20—C9—C733.3 (6)
S114—Si1—O112—C59143.4 (4)C22—C20—C9—C790.6 (5)
O112—Si1—O110—C1118.5 (4)C26—C20—C9—C1148.6 (4)
O111—Si1—O110—C1134.5 (4)C22—C20—C9—C187.5 (5)
S114—Si1—O110—C15.7 (4)C63—C61—C60—C590.1 (7)
O112—Si1—O111—C30166.6 (5)C63—C61—C60—C68178.2 (5)
O110—Si1—O111—C3055.9 (5)C70—C68—C60—C6157.5 (6)
S114—Si1—O111—C3068.7 (5)C74—C68—C60—C6166.3 (6)
Si1—O110—C1—C277.3 (5)C70—C68—C60—C59124.3 (5)
Si1—O110—C1—C9106.2 (4)C74—C68—C60—C59111.9 (5)
O110—C1—C2—C3177.0 (4)C32—C34—C36—C380.9 (8)
C9—C1—C2—C30.6 (7)C30—C38—C36—C340.0 (8)
O110—C1—C2—C100.2 (7)C49—C38—C36—C34179.4 (5)
C9—C1—C2—C10176.6 (4)C102—N109—C88—C9167.6 (5)
C32—C31—C39—C4130.7 (6)C95—N109—C88—C91163.4 (4)
C30—C31—C39—C41152.8 (4)C63—C65—C167—C591.2 (7)
C32—C31—C39—C4593.2 (5)C63—C65—C167—C78175.8 (5)
C30—C31—C39—C4583.3 (5)C80—C78—C167—C6554.3 (6)
C1—C2—C10—C16130.2 (5)C84—C78—C167—C6567.9 (6)
C3—C2—C10—C1652.6 (6)C80—C78—C167—C59128.9 (5)
C1—C2—C10—C12105.9 (5)C84—C78—C167—C59108.9 (5)
C3—C2—C10—C1271.3 (5)Si1—O112—C59—C60104.2 (5)
C7—C5—C3—C20.3 (7)Si1—O112—C59—C16780.3 (5)
C1—C2—C3—C50.6 (7)C61—C60—C59—O112177.3 (4)
C10—C2—C3—C5176.8 (4)C68—C60—C59—O1120.9 (7)
C102—N109—C95—C9858.6 (6)C61—C60—C59—C1671.9 (7)
C88—N109—C95—C9869.4 (5)C68—C60—C59—C167176.4 (4)
Si1—O111—C30—C3889.7 (6)C65—C167—C59—O112177.8 (4)
Si1—O111—C30—C3196.0 (5)C78—C167—C59—O1120.9 (7)
C36—C38—C30—O111175.3 (4)C65—C167—C59—C602.4 (7)
C49—C38—C30—O1114.1 (7)C78—C167—C59—C60174.5 (4)
C36—C38—C30—C311.2 (7)C3—C5—C7—C91.1 (7)
C49—C38—C30—C31178.2 (4)C1—C9—C7—C51.1 (7)
C32—C31—C30—O111175.8 (4)C20—C9—C7—C5177.1 (5)
C39—C31—C30—O1110.7 (6)C60—C61—C63—C651.1 (8)
C32—C31—C30—C381.5 (7)C167—C65—C63—C610.5 (8)
C39—C31—C30—C38175.0 (4)C88—N109—C102—C105174.9 (4)
C30—C31—C32—C340.7 (7)C95—N109—C102—C10557.7 (6)
C39—C31—C32—C34175.9 (5)C36—C38—C49—C5569.4 (6)
C36—C34—C32—C310.5 (8)C30—C38—C49—C55111.2 (5)
O110—C1—C9—C7176.3 (4)C36—C38—C49—C5153.1 (6)
C2—C1—C9—C70.2 (7)C30—C38—C49—C51126.3 (5)
O110—C1—C9—C205.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N109—H115···S1141.03 (6)2.11 (6)3.081 (4)157 (5)
(tdst_et3n_120) top
Crystal data top
C36H51O3SSi·C6H16NF(000) = 1520
Mr = 694.11Dx = 1.119 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1743 reflections
a = 11.6463 (11) Åθ = 3.6–29.4°
b = 17.9257 (12) ŵ = 0.14 mm1
c = 20.110 (3) ÅT = 120 K
β = 101.060 (9)°Block, colourless
V = 4120.3 (7) Å30.34 × 0.22 × 0.13 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
6269 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.057
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.2°
rotation method scansh = 1414
17343 measured reflectionsk = 2122
7408 independent reflectionsl = 2424
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.043P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.19 e Å3
7408 reflectionsΔρmin = 0.19 e Å3
452 parametersAbsolute structure: Flack x determined using 2316 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 1.07 (7)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.55615 (6)0.26115 (4)0.06092 (4)0.01183 (17)
S1140.40771 (6)0.20840 (4)0.01632 (4)0.01770 (17)
O1120.54719 (16)0.35323 (10)0.05813 (12)0.0149 (4)
O1100.59264 (16)0.23835 (11)0.14271 (11)0.0149 (4)
O1110.67399 (16)0.24752 (11)0.02826 (11)0.0147 (4)
N1090.1974 (2)0.28392 (14)0.07516 (14)0.0179 (6)
H1150.259 (3)0.266 (2)0.053 (2)0.022 (10)*
C380.7320 (2)0.14369 (16)0.03376 (17)0.0170 (6)
C780.5846 (2)0.38426 (17)0.07822 (17)0.0186 (7)
H790.53870.34340.06410.022*
C10.5325 (2)0.19585 (16)0.18234 (16)0.0154 (6)
C50.4236 (3)0.11087 (18)0.26750 (18)0.0218 (7)
H60.38670.08230.29580.026*
C310.8580 (2)0.18903 (17)0.07038 (17)0.0164 (6)
C20.4378 (2)0.22605 (17)0.20641 (17)0.0169 (6)
C390.8823 (2)0.24622 (17)0.12759 (17)0.0183 (7)
H400.80750.25890.14030.022*
C450.9325 (3)0.31792 (19)0.1023 (2)0.0257 (8)
H461.00690.30720.09050.039*
H470.94230.3550.13740.039*
H480.87970.33630.06310.039*
C100.3948 (2)0.30564 (17)0.19135 (17)0.0182 (7)
H110.43290.32560.15570.022*
C410.9639 (3)0.2165 (2)0.19059 (18)0.0261 (8)
H420.93450.16980.20360.039*
H430.96780.25170.22690.039*
H441.04070.20930.18090.039*
C220.6270 (3)0.0508 (2)0.1051 (2)0.0284 (8)
H230.58210.00810.11350.043*
H240.69120.03510.08490.043*
H250.5780.08440.07490.043*
C340.9223 (3)0.08698 (18)0.0079 (2)0.0266 (8)
H350.97830.05140.00340.032*
C200.6740 (2)0.09051 (17)0.17190 (18)0.0188 (7)
H210.72340.13190.16230.023*
C30.3840 (2)0.18169 (18)0.24937 (17)0.0198 (7)
H40.32050.20060.26580.024*
C840.4992 (3)0.43962 (19)0.1198 (2)0.0292 (8)
H850.54190.48180.13170.044*
H860.44350.4560.09350.044*
H870.45890.41560.16030.044*
C950.1070 (3)0.25019 (19)0.03925 (18)0.0224 (7)
H960.12570.2640.00820.027*
H970.11150.19630.04190.027*
C300.7525 (2)0.19174 (16)0.02212 (17)0.0152 (6)
C610.7654 (3)0.50285 (19)0.0972 (2)0.0260 (8)
H620.80310.53030.13430.031*
C320.9407 (2)0.13580 (18)0.06218 (18)0.0222 (7)
H331.01020.13290.09390.027*
C680.6596 (3)0.43437 (18)0.17706 (18)0.0220 (7)
H690.60610.39180.17460.026*
C700.7694 (3)0.4162 (2)0.2294 (2)0.0301 (8)
H710.8060.37240.21550.045*
H720.74830.40730.27260.045*
H730.82290.45740.2330.045*
C1050.2230 (3)0.3986 (2)0.0028 (2)0.0325 (8)
H1060.2390.45110.00430.049*
H1070.28920.37370.02380.049*
H1080.15550.3910.01730.049*
C90.5739 (2)0.12335 (16)0.20050 (16)0.0165 (6)
C910.2934 (3)0.2664 (2)0.1760 (2)0.0306 (8)
H920.28450.24070.21850.046*
H930.36140.24790.14580.046*
H940.30240.31890.18320.046*
C160.2621 (3)0.3089 (2)0.16583 (19)0.0258 (8)
H170.24050.27470.12880.039*
H180.23990.35860.15090.039*
H190.22280.29530.20190.039*
C600.6860 (3)0.44709 (16)0.10692 (18)0.0189 (6)
C360.8198 (3)0.09168 (18)0.03957 (18)0.0218 (7)
H370.80860.05950.07650.026*
C880.1857 (3)0.25348 (19)0.14514 (18)0.0233 (7)
H890.11870.27660.17390.028*
H900.17070.20030.14410.028*
C120.4300 (3)0.35484 (17)0.25449 (19)0.0221 (7)
H130.39560.33540.29060.033*
H140.40280.40480.24420.033*
H150.51370.3550.26810.033*
C650.7313 (3)0.47825 (18)0.02166 (19)0.0241 (7)
H660.74680.4890.06430.029*
C800.6655 (3)0.3513 (2)0.1216 (2)0.0317 (8)
H810.620.32470.15910.047*
H820.71970.31770.09480.047*
H830.70780.39080.13850.047*
C980.0171 (3)0.2745 (2)0.0681 (2)0.0296 (8)
H990.03460.26430.11590.044*
H1000.02490.3270.06070.044*
H1010.07050.24750.04620.044*
C1670.6504 (2)0.42240 (17)0.01496 (17)0.0175 (7)
C590.6304 (2)0.40640 (16)0.05011 (17)0.0159 (6)
C260.7509 (3)0.0370 (2)0.2200 (2)0.0333 (9)
H270.70870.00840.22350.05*
H280.77180.05960.26390.05*
H290.82050.02610.20280.05*
C70.5182 (3)0.08218 (18)0.24365 (17)0.0209 (7)
H80.5450.03450.25670.025*
C740.5981 (3)0.5028 (2)0.1996 (2)0.0331 (8)
H750.58270.49450.24420.05*
H760.52570.51110.16850.05*
H770.64750.54580.20010.05*
C630.7888 (3)0.51793 (19)0.03410 (19)0.0273 (8)
H640.84290.55450.02880.033*
C1020.1997 (3)0.36735 (18)0.07409 (18)0.0231 (7)
H1030.12520.38610.09830.028*
H1040.260.38470.09760.028*
C490.6219 (3)0.14596 (17)0.08856 (17)0.0197 (7)
H500.57630.18970.08030.024*
C550.5449 (3)0.07651 (19)0.0872 (2)0.0268 (8)
H560.58670.0330.09710.04*
H570.47440.08170.12060.04*
H580.52560.07150.04310.04*
C510.6516 (3)0.1539 (2)0.15909 (19)0.0285 (8)
H520.70030.1970.16010.043*
H530.58080.15960.19210.043*
H540.69250.11020.16940.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0101 (3)0.0121 (4)0.0133 (5)0.0000 (3)0.0022 (3)0.0000 (3)
S1140.0134 (3)0.0158 (4)0.0219 (4)0.0024 (3)0.0016 (3)0.0002 (3)
O1120.0126 (8)0.0142 (10)0.0180 (12)0.0014 (8)0.0033 (8)0.0012 (9)
O1100.0129 (9)0.0177 (10)0.0145 (12)0.0003 (8)0.0035 (8)0.0016 (9)
O1110.0119 (8)0.0157 (11)0.0169 (12)0.0024 (7)0.0037 (8)0.0008 (8)
N1090.0155 (12)0.0218 (14)0.0154 (15)0.0007 (10)0.0002 (11)0.0019 (11)
C380.0190 (14)0.0151 (15)0.0177 (18)0.0000 (11)0.0055 (13)0.0014 (12)
C780.0197 (14)0.0191 (16)0.0171 (18)0.0034 (11)0.0037 (13)0.0020 (13)
C10.0145 (12)0.0184 (15)0.0122 (16)0.0019 (11)0.0002 (11)0.0011 (12)
C50.0260 (15)0.0233 (17)0.0174 (18)0.0071 (12)0.0070 (14)0.0001 (13)
C310.0144 (12)0.0203 (16)0.0154 (17)0.0011 (11)0.0050 (12)0.0034 (12)
C20.0138 (12)0.0200 (16)0.0160 (17)0.0018 (11)0.0006 (12)0.0009 (12)
C390.0132 (12)0.0223 (17)0.0200 (18)0.0012 (11)0.0048 (12)0.0028 (13)
C450.0206 (14)0.0268 (18)0.030 (2)0.0042 (13)0.0050 (14)0.0059 (15)
C100.0170 (13)0.0205 (16)0.0184 (18)0.0034 (11)0.0066 (12)0.0021 (13)
C410.0219 (15)0.037 (2)0.0184 (19)0.0050 (13)0.0012 (14)0.0030 (15)
C220.0319 (17)0.0295 (19)0.025 (2)0.0063 (14)0.0075 (15)0.0039 (15)
C340.0231 (16)0.0212 (16)0.035 (2)0.0081 (13)0.0037 (15)0.0006 (15)
C200.0182 (13)0.0155 (15)0.0227 (19)0.0016 (11)0.0041 (13)0.0030 (13)
C30.0196 (13)0.0249 (17)0.0165 (18)0.0017 (12)0.0078 (13)0.0018 (13)
C840.0251 (15)0.0293 (19)0.030 (2)0.0039 (14)0.0036 (15)0.0014 (16)
C950.0204 (14)0.0287 (19)0.0182 (19)0.0026 (12)0.0042 (13)0.0050 (14)
C300.0148 (13)0.0135 (15)0.0188 (17)0.0022 (10)0.0070 (12)0.0009 (12)
C610.0267 (16)0.0224 (17)0.027 (2)0.0086 (13)0.0019 (14)0.0039 (14)
C320.0151 (14)0.0243 (17)0.025 (2)0.0047 (12)0.0004 (13)0.0021 (14)
C680.0266 (15)0.0201 (16)0.0195 (19)0.0055 (12)0.0049 (13)0.0029 (13)
C700.0340 (18)0.0309 (19)0.025 (2)0.0000 (15)0.0033 (16)0.0027 (16)
C1050.047 (2)0.0217 (18)0.029 (2)0.0039 (15)0.0061 (17)0.0030 (15)
C90.0170 (13)0.0170 (15)0.0143 (17)0.0016 (11)0.0002 (12)0.0020 (12)
C910.0349 (18)0.036 (2)0.024 (2)0.0033 (15)0.0139 (16)0.0060 (16)
C160.0181 (14)0.036 (2)0.023 (2)0.0052 (13)0.0031 (14)0.0026 (15)
C600.0177 (13)0.0175 (15)0.0211 (18)0.0009 (12)0.0025 (12)0.0003 (13)
C360.0249 (15)0.0190 (16)0.0216 (19)0.0030 (12)0.0048 (14)0.0045 (13)
C880.0250 (15)0.0268 (18)0.0175 (19)0.0021 (13)0.0026 (13)0.0032 (14)
C120.0229 (15)0.0180 (16)0.025 (2)0.0054 (12)0.0047 (14)0.0010 (14)
C650.0272 (16)0.0241 (17)0.022 (2)0.0056 (13)0.0063 (14)0.0055 (14)
C800.0289 (17)0.038 (2)0.028 (2)0.0009 (15)0.0063 (16)0.0094 (16)
C980.0182 (14)0.049 (2)0.022 (2)0.0020 (14)0.0039 (14)0.0063 (17)
C1670.0174 (13)0.0164 (15)0.0190 (18)0.0005 (11)0.0044 (13)0.0008 (12)
C590.0134 (12)0.0117 (14)0.0226 (18)0.0001 (10)0.0037 (12)0.0019 (13)
C260.0293 (17)0.032 (2)0.037 (2)0.0120 (15)0.0022 (16)0.0035 (17)
C70.0254 (15)0.0167 (16)0.0192 (19)0.0034 (12)0.0010 (13)0.0027 (13)
C740.0390 (19)0.036 (2)0.026 (2)0.0058 (16)0.0093 (17)0.0007 (17)
C630.0286 (16)0.0227 (17)0.030 (2)0.0116 (13)0.0050 (15)0.0015 (15)
C1020.0277 (15)0.0204 (16)0.0219 (19)0.0022 (12)0.0065 (14)0.0024 (14)
C490.0201 (14)0.0211 (16)0.0168 (18)0.0048 (12)0.0009 (13)0.0022 (13)
C550.0246 (15)0.0287 (19)0.024 (2)0.0017 (13)0.0019 (14)0.0052 (15)
C510.0370 (18)0.0325 (19)0.0163 (19)0.0085 (15)0.0057 (15)0.0001 (15)
Geometric parameters (Å, º) top
Si1—O1111.649 (2)C61—C601.400 (4)
Si1—O1121.654 (2)C61—H620.93
Si1—O1101.669 (2)C32—H330.93
Si1—S1142.0230 (10)C68—C601.517 (5)
O112—C591.390 (3)C68—C701.527 (5)
O110—C11.385 (4)C68—C741.532 (5)
O111—C301.377 (3)C68—H690.98
N109—C881.491 (4)C70—H710.96
N109—C1021.496 (4)C70—H720.96
N109—C951.512 (4)C70—H730.96
N109—H1150.83 (4)C105—C1021.515 (5)
C38—C301.400 (4)C105—H1060.96
C38—C361.405 (4)C105—H1070.96
C38—C491.522 (4)C105—H1080.96
C78—C1671.516 (4)C9—C71.391 (4)
C78—C801.522 (5)C91—C881.521 (4)
C78—C841.534 (4)C91—H920.96
C78—H790.98C91—H930.96
C1—C21.396 (4)C91—H940.96
C1—C91.410 (4)C16—H170.96
C5—C31.376 (5)C16—H180.96
C5—C71.383 (5)C16—H190.96
C5—H60.93C60—C591.404 (4)
C31—C321.388 (4)C36—H370.93
C31—C301.412 (4)C88—H890.97
C31—C391.526 (4)C88—H900.97
C2—C31.407 (4)C12—H130.96
C2—C101.523 (4)C12—H140.96
C39—C411.527 (5)C12—H150.96
C39—C451.539 (4)C65—C631.387 (5)
C39—H400.98C65—C1671.399 (4)
C45—H460.96C65—H660.93
C45—H470.96C80—H810.96
C45—H480.96C80—H820.96
C10—C161.534 (4)C80—H830.96
C10—C121.536 (5)C98—H990.96
C10—H110.98C98—H1000.96
C41—H420.96C98—H1010.96
C41—H430.96C167—C591.402 (5)
C41—H440.96C26—H270.96
C22—C201.526 (5)C26—H280.96
C22—H230.96C26—H290.96
C22—H240.96C7—H80.93
C22—H250.96C74—H750.96
C34—C361.380 (5)C74—H760.96
C34—C321.384 (5)C74—H770.96
C34—H350.93C63—H640.93
C20—C91.514 (4)C102—H1030.97
C20—C261.525 (4)C102—H1040.97
C20—H210.98C49—C511.530 (5)
C3—H40.93C49—C551.537 (4)
C84—H850.96C49—H500.98
C84—H860.96C55—H560.96
C84—H870.96C55—H570.96
C95—C981.515 (4)C55—H580.96
C95—H960.97C51—H520.96
C95—H970.97C51—H530.96
C61—C631.375 (5)C51—H540.96
O111—Si1—O112100.74 (10)H71—C70—H72109.5
O111—Si1—O110106.39 (10)C68—C70—H73109.5
O112—Si1—O110106.28 (11)H71—C70—H73109.5
O111—Si1—S114117.38 (9)H72—C70—H73109.5
O112—Si1—S114114.11 (8)C102—C105—H106109.5
O110—Si1—S114110.90 (8)C102—C105—H107109.5
C59—O112—Si1130.32 (17)H106—C105—H107109.5
C1—O110—Si1129.83 (17)C102—C105—H108109.5
C30—O111—Si1139.58 (19)H106—C105—H108109.5
C88—N109—C102112.2 (3)H107—C105—H108109.5
C88—N109—C95111.0 (2)C7—C9—C1118.2 (3)
C102—N109—C95113.9 (3)C7—C9—C20121.1 (3)
C88—N109—H115106 (3)C1—C9—C20120.7 (3)
C102—N109—H115112 (2)C88—C91—H92109.5
C95—N109—H115102 (3)C88—C91—H93109.5
C30—C38—C36117.4 (3)H92—C91—H93109.5
C30—C38—C49123.7 (3)C88—C91—H94109.5
C36—C38—C49118.9 (3)H92—C91—H94109.5
C167—C78—C80112.8 (2)H93—C91—H94109.5
C167—C78—C84109.6 (3)C10—C16—H17109.5
C80—C78—C84110.2 (3)C10—C16—H18109.5
C167—C78—H79108H17—C16—H18109.5
C80—C78—H79108C10—C16—H19109.5
C84—C78—H79108H17—C16—H19109.5
O110—C1—C2120.4 (2)H18—C16—H19109.5
O110—C1—C9118.1 (2)C61—C60—C59118.1 (3)
C2—C1—C9121.4 (3)C61—C60—C68119.6 (3)
C3—C5—C7120.0 (3)C59—C60—C68122.3 (3)
C3—C5—H6120C34—C36—C38122.0 (3)
C7—C5—H6120C34—C36—H37119
C32—C31—C30118.3 (3)C38—C36—H37119
C32—C31—C39121.2 (3)N109—C88—C91113.3 (3)
C30—C31—C39120.4 (3)N109—C88—H89108.9
C1—C2—C3118.0 (3)C91—C88—H89108.9
C1—C2—C10123.1 (3)N109—C88—H90108.9
C3—C2—C10118.9 (3)C91—C88—H90108.9
C41—C39—C31112.8 (3)H89—C88—H90107.7
C41—C39—C45110.5 (2)C10—C12—H13109.5
C31—C39—C45109.8 (3)C10—C12—H14109.5
C41—C39—H40107.9H13—C12—H14109.5
C31—C39—H40107.9C10—C12—H15109.5
C45—C39—H40107.9H13—C12—H15109.5
C39—C45—H46109.5H14—C12—H15109.5
C39—C45—H47109.5C63—C65—C167121.3 (3)
H46—C45—H47109.5C63—C65—H66119.4
C39—C45—H48109.5C167—C65—H66119.4
H46—C45—H48109.5C78—C80—H81109.5
H47—C45—H48109.5C78—C80—H82109.5
C2—C10—C16111.9 (3)H81—C80—H82109.5
C2—C10—C12110.4 (3)C78—C80—H83109.5
C16—C10—C12110.3 (3)H81—C80—H83109.5
C2—C10—H11108H82—C80—H83109.5
C16—C10—H11108C95—C98—H99109.5
C12—C10—H11108C95—C98—H100109.5
C39—C41—H42109.5H99—C98—H100109.5
C39—C41—H43109.5C95—C98—H101109.5
H42—C41—H43109.5H99—C98—H101109.5
C39—C41—H44109.5H100—C98—H101109.5
H42—C41—H44109.5C65—C167—C59118.1 (3)
H43—C41—H44109.5C65—C167—C78118.9 (3)
C20—C22—H23109.5C59—C167—C78122.9 (3)
C20—C22—H24109.5O112—C59—C167119.5 (3)
H23—C22—H24109.5O112—C59—C60119.0 (3)
C20—C22—H25109.5C167—C59—C60121.3 (3)
H23—C22—H25109.5C20—C26—H27109.5
H24—C22—H25109.5C20—C26—H28109.5
C36—C34—C32119.4 (3)H27—C26—H28109.5
C36—C34—H35120.3C20—C26—H29109.5
C32—C34—H35120.3H27—C26—H29109.5
C9—C20—C26113.9 (3)H28—C26—H29109.5
C9—C20—C22110.1 (2)C5—C7—C9121.2 (3)
C26—C20—C22109.4 (3)C5—C7—H8119.4
C9—C20—H21107.7C9—C7—H8119.4
C26—C20—H21107.7C68—C74—H75109.5
C22—C20—H21107.7C68—C74—H76109.5
C5—C3—C2121.2 (3)H75—C74—H76109.5
C5—C3—H4119.4C68—C74—H77109.5
C2—C3—H4119.4H75—C74—H77109.5
C78—C84—H85109.5H76—C74—H77109.5
C78—C84—H86109.5C61—C63—C65119.7 (3)
H85—C84—H86109.5C61—C63—H64120.2
C78—C84—H87109.5C65—C63—H64120.2
H85—C84—H87109.5N109—C102—C105112.5 (3)
H86—C84—H87109.5N109—C102—H103109.1
N109—C95—C98113.7 (3)C105—C102—H103109.1
N109—C95—H96108.8N109—C102—H104109.1
C98—C95—H96108.8C105—C102—H104109.1
N109—C95—H97108.8H103—C102—H104107.8
C98—C95—H97108.8C38—C49—C51111.4 (3)
H96—C95—H97107.7C38—C49—C55112.2 (3)
O111—C30—C38120.3 (3)C51—C49—C55109.2 (3)
O111—C30—C31117.9 (3)C38—C49—H50108
C38—C30—C31121.5 (3)C51—C49—H50108
C63—C61—C60121.5 (3)C55—C49—H50108
C63—C61—H62119.3C49—C55—H56109.5
C60—C61—H62119.3C49—C55—H57109.5
C34—C32—C31121.5 (3)H56—C55—H57109.5
C34—C32—H33119.3C49—C55—H58109.5
C31—C32—H33119.3H56—C55—H58109.5
C60—C68—C70112.4 (3)H57—C55—H58109.5
C60—C68—C74110.1 (3)C49—C51—H52109.5
C70—C68—C74110.1 (3)C49—C51—H53109.5
C60—C68—H69108H52—C51—H53109.5
C70—C68—H69108C49—C51—H54109.5
C74—C68—H69108H52—C51—H54109.5
C68—C70—H71109.5H53—C51—H54109.5
C68—C70—H72109.5
O111—Si1—O112—C5916.9 (3)C2—C1—C9—C20177.8 (3)
O110—Si1—O112—C5993.9 (3)C26—C20—C9—C733.8 (4)
S114—Si1—O112—C59143.6 (2)C22—C20—C9—C789.5 (3)
O111—Si1—O110—C1134.6 (2)C26—C20—C9—C1148.1 (3)
O112—Si1—O110—C1118.6 (2)C22—C20—C9—C188.5 (3)
S114—Si1—O110—C15.9 (2)C63—C61—C60—C590.1 (5)
O112—Si1—O111—C30166.2 (3)C63—C61—C60—C68177.8 (3)
O110—Si1—O111—C3055.5 (3)C70—C68—C60—C6157.9 (4)
S114—Si1—O111—C3069.3 (3)C74—C68—C60—C6165.3 (4)
Si1—O110—C1—C277.3 (3)C70—C68—C60—C59124.3 (3)
Si1—O110—C1—C9106.2 (3)C74—C68—C60—C59112.5 (3)
O110—C1—C2—C3176.7 (3)C32—C34—C36—C381.4 (5)
C9—C1—C2—C30.3 (4)C30—C38—C36—C340.6 (5)
O110—C1—C2—C100.0 (4)C49—C38—C36—C34179.4 (3)
C9—C1—C2—C10176.4 (3)C102—N109—C88—C9168.6 (4)
C32—C31—C39—C4130.7 (4)C95—N109—C88—C91162.7 (3)
C30—C31—C39—C41152.8 (3)C63—C65—C167—C591.3 (5)
C32—C31—C39—C4593.0 (3)C63—C65—C167—C78176.2 (3)
C30—C31—C39—C4583.5 (3)C80—C78—C167—C6554.6 (4)
C1—C2—C10—C16130.8 (3)C84—C78—C167—C6568.7 (4)
C3—C2—C10—C1652.6 (4)C80—C78—C167—C59128.1 (3)
C1—C2—C10—C12106.0 (3)C84—C78—C167—C59108.6 (3)
C3—C2—C10—C1270.7 (3)Si1—O112—C59—C16781.0 (3)
C7—C5—C3—C20.2 (5)Si1—O112—C59—C60104.0 (3)
C1—C2—C3—C50.3 (5)C65—C167—C59—O112177.5 (3)
C10—C2—C3—C5176.5 (3)C78—C167—C59—O1120.2 (4)
C88—N109—C95—C9868.8 (4)C65—C167—C59—C602.6 (4)
C102—N109—C95—C9859.0 (4)C78—C167—C59—C60174.7 (3)
Si1—O111—C30—C3889.9 (4)C61—C60—C59—O112177.0 (3)
Si1—O111—C30—C3195.5 (3)C68—C60—C59—O1120.8 (4)
C36—C38—C30—O111175.3 (3)C61—C60—C59—C1672.1 (4)
C49—C38—C30—O1113.4 (4)C68—C60—C59—C167175.7 (3)
C36—C38—C30—C310.9 (5)C3—C5—C7—C90.9 (5)
C49—C38—C30—C31177.8 (3)C1—C9—C7—C50.9 (4)
C32—C31—C30—O111176.1 (3)C20—C9—C7—C5177.2 (3)
C39—C31—C30—O1110.5 (4)C60—C61—C63—C651.2 (5)
C32—C31—C30—C381.6 (5)C167—C65—C63—C610.6 (5)
C39—C31—C30—C38175.0 (3)C88—N109—C102—C105174.6 (3)
C36—C34—C32—C310.6 (5)C95—N109—C102—C10558.2 (4)
C30—C31—C32—C340.9 (5)C30—C38—C49—C51125.5 (3)
C39—C31—C32—C34175.7 (3)C36—C38—C49—C5153.1 (4)
O110—C1—C9—C7176.2 (3)C30—C38—C49—C55111.7 (3)
C2—C1—C9—C70.3 (4)C36—C38—C49—C5569.6 (4)
O110—C1—C9—C205.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N109—H115···S1140.83 (4)2.26 (4)3.080 (3)171 (4)
(tdst_et3n_150) top
Crystal data top
C36H51O3SSi·C6H16NF(000) = 1520
Mr = 694.11Dx = 1.113 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3815 reflections
a = 11.6801 (9) Åθ = 3.1–29.4°
b = 17.9212 (10) ŵ = 0.14 mm1
c = 20.1555 (15) ÅT = 150 K
β = 100.954 (6)°Block, colourless
V = 4142.1 (5) Å30.34 × 0.22 × 0.13 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
7216 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.039
Detector resolution: 6.67 pixels mm-1θmax = 26°, θmin = 3.2°
rotation method scansh = 1414
19022 measured reflectionsk = 1922
7810 independent reflectionsl = 2424
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.03 w = 1/[σ2(Fo2) + (0.0451P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.071(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.23 e Å3
7810 reflectionsΔρmin = 0.17 e Å3
452 parametersAbsolute structure: Flack x determined using 3205 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 0.04 (3)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.55626 (4)0.26140 (3)0.06097 (3)0.01445 (13)
S1140.40810 (5)0.20879 (3)0.01650 (3)0.02146 (13)
O1120.54732 (13)0.35346 (8)0.05794 (8)0.0181 (3)
O1100.59257 (13)0.23884 (8)0.14250 (8)0.0177 (3)
O1110.67377 (14)0.24773 (8)0.02844 (8)0.0185 (3)
N1090.19765 (18)0.28372 (11)0.07493 (10)0.0222 (4)
H1150.266 (3)0.2664 (14)0.0511 (14)0.018 (6)*
C380.7317 (2)0.14370 (12)0.03375 (12)0.0212 (5)
C780.5842 (2)0.38475 (13)0.07806 (12)0.0226 (5)
H790.53910.34360.06380.027*
C10.53260 (19)0.19626 (12)0.18209 (11)0.0174 (4)
C50.4244 (2)0.11108 (14)0.26751 (13)0.0270 (5)
H60.38820.08260.29610.032*
C310.8571 (2)0.18966 (13)0.07026 (12)0.0212 (5)
C20.4383 (2)0.22653 (13)0.20655 (12)0.0199 (5)
C390.8817 (2)0.24697 (13)0.12729 (13)0.0234 (5)
H400.80730.25980.140.028*
C450.9318 (2)0.31828 (14)0.10204 (15)0.0307 (6)
H461.00610.30750.09040.046*
H470.94150.35540.1370.046*
H480.87940.33660.06290.046*
C100.3948 (2)0.30564 (13)0.19132 (13)0.0226 (5)
H110.43290.32560.15570.027*
C410.9630 (2)0.21747 (16)0.19026 (14)0.0330 (6)
H420.93290.17130.20390.049*
H430.96790.25330.22610.049*
H441.03920.20930.18030.049*
C220.6260 (3)0.04990 (16)0.10513 (15)0.0369 (6)
H230.58470.0060.11450.055*
H240.68950.03580.08380.055*
H250.57390.08220.07560.055*
C340.9214 (2)0.08725 (14)0.00793 (15)0.0318 (6)
H350.97710.05150.00330.038*
C200.6733 (2)0.09074 (13)0.17104 (13)0.0239 (5)
H210.72170.13220.16050.029*
C30.3847 (2)0.18211 (14)0.24927 (12)0.0237 (5)
H40.32120.20090.26560.028*
C840.4982 (3)0.43934 (16)0.11949 (16)0.0368 (6)
H850.53980.48230.13070.055*
H860.44140.45460.09350.055*
H870.45970.41540.16020.055*
C950.1072 (2)0.25011 (15)0.03936 (14)0.0279 (5)
H960.12520.26420.00790.034*
H970.1120.19620.04170.034*
C300.75226 (19)0.19224 (12)0.02244 (12)0.0182 (4)
C610.7638 (2)0.50320 (14)0.09678 (15)0.0320 (6)
H620.80120.53070.13370.038*
C320.9401 (2)0.13654 (14)0.06229 (13)0.0271 (5)
H331.00940.13390.09380.033*
C680.6589 (2)0.43453 (14)0.17677 (13)0.0268 (5)
H690.60580.39190.17440.032*
C700.7683 (3)0.41673 (16)0.22852 (15)0.0370 (6)
H710.80460.37280.21470.055*
H720.74770.40820.27180.055*
H730.82160.45790.23170.055*
C1050.2240 (3)0.39817 (16)0.00330 (16)0.0403 (7)
H1060.23730.45090.0050.06*
H1070.29180.37440.02240.06*
H1080.15820.3890.01780.06*
C90.57391 (19)0.12372 (12)0.19993 (11)0.0193 (4)
C910.2937 (3)0.26519 (18)0.17497 (16)0.0392 (7)
H920.28470.24020.21780.059*
H930.36060.24560.14490.059*
H940.3040.31770.18120.059*
C160.2631 (2)0.30863 (16)0.16579 (14)0.0321 (6)
H170.24160.2730.130.048*
H180.24130.35780.14910.048*
H190.22370.2970.20220.048*
C600.6852 (2)0.44734 (12)0.10668 (13)0.0228 (5)
C360.8193 (2)0.09208 (13)0.03888 (14)0.0278 (5)
H370.80810.05960.07550.033*
C880.1863 (2)0.25263 (15)0.14504 (14)0.0304 (6)
H890.11990.27580.1740.037*
H900.17110.19950.14390.037*
C120.4296 (2)0.35478 (14)0.25411 (14)0.0287 (6)
H130.39360.33610.28980.043*
H140.40430.40510.24350.043*
H150.51290.35390.26840.043*
C650.7302 (2)0.47895 (14)0.02148 (14)0.0302 (6)
H660.74560.490.0640.036*
C800.6654 (3)0.35222 (18)0.12160 (16)0.0401 (7)
H810.62050.32460.15840.06*
H820.72080.31960.09470.06*
H830.7060.3920.13910.06*
C980.0164 (2)0.27396 (18)0.06864 (16)0.0383 (7)
H990.03310.26370.11620.058*
H1000.02460.32650.06140.058*
H1010.06980.24680.04690.058*
C1670.6498 (2)0.42274 (13)0.01519 (12)0.0220 (5)
C590.62953 (19)0.40688 (11)0.04986 (12)0.0185 (4)
C260.7517 (3)0.03854 (17)0.21967 (17)0.0413 (7)
H270.70990.00640.22530.062*
H280.77470.06270.26270.062*
H290.81990.02650.20160.062*
C70.5183 (2)0.08235 (13)0.24301 (13)0.0249 (5)
H80.54470.03450.25560.03*
C740.5974 (3)0.50292 (17)0.19895 (16)0.0410 (7)
H750.58060.49440.24310.061*
H760.52590.51150.16750.061*
H770.6470.54580.20010.061*
C630.7873 (3)0.51856 (15)0.03397 (15)0.0347 (6)
H640.84110.55530.02870.042*
C1020.1998 (2)0.36690 (14)0.07414 (14)0.0296 (6)
H1030.12530.38560.09790.036*
H1040.25950.38420.0980.036*
C490.6219 (2)0.14621 (13)0.08790 (13)0.0242 (5)
H500.57630.18990.07940.029*
C550.5457 (2)0.07665 (15)0.08719 (15)0.0342 (6)
H560.58770.03340.09740.051*
H570.47550.08190.12050.051*
H580.52610.07110.04330.051*
C510.6516 (3)0.15457 (16)0.15873 (14)0.0368 (6)
H520.69970.19790.15970.055*
H530.58090.160.19160.055*
H540.69270.1110.16910.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0134 (3)0.0145 (3)0.0158 (3)0.0002 (2)0.0036 (2)0.0000 (2)
S1140.0171 (3)0.0182 (2)0.0271 (3)0.0029 (2)0.0010 (2)0.0004 (2)
O1120.0169 (7)0.0164 (7)0.0213 (8)0.0010 (6)0.0046 (6)0.0000 (6)
O1100.0161 (7)0.0203 (7)0.0170 (8)0.0006 (6)0.0040 (6)0.0025 (6)
O1110.0179 (7)0.0179 (7)0.0209 (9)0.0020 (6)0.0068 (7)0.0000 (6)
N1090.0199 (10)0.0274 (10)0.0187 (11)0.0003 (8)0.0017 (9)0.0019 (8)
C380.0238 (12)0.0203 (11)0.0212 (12)0.0003 (9)0.0080 (10)0.0013 (9)
C780.0261 (12)0.0224 (11)0.0200 (12)0.0039 (9)0.0057 (10)0.0018 (9)
C10.0170 (10)0.0213 (11)0.0132 (11)0.0037 (8)0.0008 (9)0.0001 (8)
C50.0347 (13)0.0277 (12)0.0205 (13)0.0087 (10)0.0105 (11)0.0004 (9)
C310.0204 (11)0.0231 (11)0.0210 (12)0.0007 (9)0.0060 (10)0.0016 (9)
C20.0186 (10)0.0248 (11)0.0156 (12)0.0024 (8)0.0012 (9)0.0007 (8)
C390.0183 (11)0.0287 (13)0.0237 (13)0.0015 (9)0.0052 (10)0.0045 (9)
C450.0273 (12)0.0300 (13)0.0356 (15)0.0056 (10)0.0082 (12)0.0065 (11)
C100.0196 (11)0.0272 (12)0.0229 (13)0.0043 (9)0.0089 (10)0.0032 (9)
C410.0270 (13)0.0454 (15)0.0250 (14)0.0053 (11)0.0010 (12)0.0037 (11)
C220.0427 (16)0.0388 (15)0.0308 (15)0.0088 (12)0.0108 (13)0.0074 (12)
C340.0304 (13)0.0278 (12)0.0374 (16)0.0109 (11)0.0067 (12)0.0030 (11)
C200.0233 (11)0.0183 (11)0.0308 (14)0.0019 (9)0.0067 (11)0.0026 (9)
C30.0233 (11)0.0304 (12)0.0193 (13)0.0036 (9)0.0088 (10)0.0033 (9)
C840.0342 (14)0.0366 (14)0.0362 (16)0.0014 (12)0.0022 (13)0.0006 (12)
C950.0249 (12)0.0367 (14)0.0221 (13)0.0041 (10)0.0042 (11)0.0072 (10)
C300.0176 (10)0.0174 (10)0.0212 (12)0.0015 (8)0.0079 (10)0.0022 (8)
C610.0353 (14)0.0260 (12)0.0332 (16)0.0119 (11)0.0030 (12)0.0048 (10)
C320.0205 (12)0.0312 (12)0.0279 (15)0.0054 (10)0.0002 (11)0.0029 (10)
C680.0327 (13)0.0252 (12)0.0225 (13)0.0078 (10)0.0054 (11)0.0037 (9)
C700.0462 (16)0.0349 (14)0.0290 (16)0.0006 (12)0.0049 (13)0.0035 (11)
C1050.0588 (19)0.0290 (14)0.0332 (16)0.0056 (13)0.0092 (15)0.0036 (11)
C90.0205 (11)0.0207 (11)0.0156 (12)0.0028 (9)0.0009 (9)0.0016 (9)
C910.0455 (17)0.0459 (17)0.0300 (16)0.0051 (13)0.0171 (14)0.0095 (12)
C160.0226 (12)0.0449 (15)0.0283 (15)0.0070 (11)0.0034 (11)0.0032 (11)
C600.0248 (11)0.0182 (11)0.0249 (13)0.0025 (9)0.0034 (10)0.0001 (9)
C360.0309 (13)0.0224 (11)0.0303 (14)0.0053 (10)0.0067 (11)0.0069 (10)
C880.0314 (13)0.0379 (14)0.0214 (14)0.0039 (11)0.0034 (12)0.0056 (10)
C120.0305 (13)0.0244 (12)0.0309 (15)0.0053 (10)0.0050 (12)0.0001 (10)
C650.0354 (14)0.0292 (13)0.0268 (14)0.0082 (11)0.0083 (12)0.0055 (10)
C800.0382 (16)0.0470 (17)0.0366 (17)0.0005 (13)0.0105 (14)0.0118 (13)
C980.0236 (13)0.0629 (19)0.0285 (16)0.0019 (13)0.0048 (12)0.0086 (13)
C1670.0237 (11)0.0198 (11)0.0230 (13)0.0001 (9)0.0055 (10)0.0009 (9)
C590.0164 (10)0.0138 (10)0.0254 (13)0.0016 (8)0.0039 (10)0.0022 (9)
C260.0352 (15)0.0415 (16)0.0447 (19)0.0152 (12)0.0012 (14)0.0053 (13)
C70.0332 (13)0.0199 (11)0.0210 (13)0.0032 (9)0.0036 (11)0.0026 (9)
C740.0494 (17)0.0434 (16)0.0321 (17)0.0100 (13)0.0125 (15)0.0004 (13)
C630.0375 (14)0.0283 (13)0.0388 (16)0.0152 (11)0.0088 (13)0.0016 (11)
C1020.0363 (14)0.0260 (12)0.0273 (14)0.0022 (10)0.0083 (12)0.0023 (10)
C490.0259 (12)0.0260 (12)0.0200 (13)0.0048 (9)0.0028 (10)0.0035 (9)
C550.0349 (14)0.0355 (14)0.0298 (15)0.0033 (11)0.0004 (12)0.0047 (11)
C510.0474 (16)0.0417 (15)0.0222 (14)0.0102 (13)0.0088 (13)0.0004 (11)
Geometric parameters (Å, º) top
Si1—O1111.6481 (16)C61—C601.398 (3)
Si1—O1121.6535 (15)C61—H620.93
Si1—O1101.6670 (16)C32—H330.93
Si1—S1142.0242 (8)C68—C601.519 (3)
O112—C591.387 (3)C68—C701.522 (4)
O110—C11.386 (3)C68—C741.530 (4)
O111—C301.373 (3)C68—H690.98
N109—C1021.491 (3)C70—H710.96
N109—C881.501 (3)C70—H720.96
N109—C951.510 (3)C70—H730.96
N109—H1150.91 (3)C105—C1021.510 (4)
C38—C361.398 (3)C105—H1060.96
C38—C301.412 (3)C105—H1070.96
C38—C491.518 (4)C105—H1080.96
C78—C1671.512 (3)C9—C71.393 (3)
C78—C801.525 (4)C91—C881.509 (4)
C78—C841.531 (4)C91—H920.96
C78—H790.98C91—H930.96
C1—C21.399 (3)C91—H940.96
C1—C91.409 (3)C16—H170.96
C5—C31.381 (4)C16—H180.96
C5—C71.385 (4)C16—H190.96
C5—H60.93C60—C591.406 (3)
C31—C321.390 (3)C36—H370.93
C31—C301.408 (3)C88—H890.97
C31—C391.527 (3)C88—H900.97
C2—C31.404 (3)C12—H130.96
C2—C101.518 (3)C12—H140.96
C39—C411.527 (4)C12—H150.96
C39—C451.532 (3)C65—C631.384 (4)
C39—H400.98C65—C1671.399 (3)
C45—H460.96C65—H660.93
C45—H470.96C80—H810.96
C45—H480.96C80—H820.96
C10—C161.527 (3)C80—H830.96
C10—C121.532 (4)C98—H990.96
C10—H110.98C98—H1000.96
C41—H420.96C98—H1010.96
C41—H430.96C167—C591.405 (3)
C41—H440.96C26—H270.96
C22—C201.526 (4)C26—H280.96
C22—H230.96C26—H290.96
C22—H240.96C7—H80.93
C22—H250.96C74—H750.96
C34—C361.375 (4)C74—H760.96
C34—C321.392 (4)C74—H770.96
C34—H350.93C63—H640.93
C20—C91.515 (3)C102—H1030.97
C20—C261.527 (4)C102—H1040.97
C20—H210.98C49—C551.534 (4)
C3—H40.93C49—C511.539 (4)
C84—H850.96C49—H500.98
C84—H860.96C55—H560.96
C84—H870.96C55—H570.96
C95—C981.514 (4)C55—H580.96
C95—H960.97C51—H520.96
C95—H970.97C51—H530.96
C61—C631.373 (4)C51—H540.96
O111—Si1—O112100.67 (8)H71—C70—H72109.5
O111—Si1—O110106.32 (8)C68—C70—H73109.5
O112—Si1—O110106.32 (8)H71—C70—H73109.5
O111—Si1—S114117.46 (6)H72—C70—H73109.5
O112—Si1—S114113.94 (7)C102—C105—H106109.5
O110—Si1—S114111.07 (6)C102—C105—H107109.5
C59—O112—Si1130.74 (14)H106—C105—H107109.5
C1—O110—Si1129.73 (14)C102—C105—H108109.5
C30—O111—Si1139.73 (14)H106—C105—H108109.5
C102—N109—C88112.29 (19)H107—C105—H108109.5
C102—N109—C95113.95 (19)C7—C9—C1118.2 (2)
C88—N109—C95110.73 (19)C7—C9—C20121.0 (2)
C102—N109—H115108.9 (16)C1—C9—C20120.81 (19)
C88—N109—H115106.5 (17)C88—C91—H92109.5
C95—N109—H115103.8 (17)C88—C91—H93109.5
C36—C38—C30116.9 (2)H92—C91—H93109.5
C36—C38—C49119.8 (2)C88—C91—H94109.5
C30—C38—C49123.4 (2)H92—C91—H94109.5
C167—C78—C80112.5 (2)H93—C91—H94109.5
C167—C78—C84110.2 (2)C10—C16—H17109.5
C80—C78—C84110.2 (2)C10—C16—H18109.5
C167—C78—H79107.9H17—C16—H18109.5
C80—C78—H79107.9C10—C16—H19109.5
C84—C78—H79107.9H17—C16—H19109.5
O110—C1—C2120.47 (19)H18—C16—H19109.5
O110—C1—C9117.95 (18)C61—C60—C59117.9 (2)
C2—C1—C9121.47 (19)C61—C60—C68119.7 (2)
C3—C5—C7119.8 (2)C59—C60—C68122.4 (2)
C3—C5—H6120.1C34—C36—C38122.8 (2)
C7—C5—H6120.1C34—C36—H37118.6
C32—C31—C30118.6 (2)C38—C36—H37118.6
C32—C31—C39120.8 (2)N109—C88—C91112.9 (2)
C30—C31—C39120.5 (2)N109—C88—H89109
C1—C2—C3118.0 (2)C91—C88—H89109
C1—C2—C10123.15 (19)N109—C88—H90109
C3—C2—C10118.8 (2)C91—C88—H90109
C31—C39—C41113.0 (2)H89—C88—H90107.8
C31—C39—C45109.9 (2)C10—C12—H13109.5
C41—C39—C45110.4 (2)C10—C12—H14109.5
C31—C39—H40107.8H13—C12—H14109.5
C41—C39—H40107.8C10—C12—H15109.5
C45—C39—H40107.8H13—C12—H15109.5
C39—C45—H46109.5H14—C12—H15109.5
C39—C45—H47109.5C63—C65—C167121.7 (2)
H46—C45—H47109.5C63—C65—H66119.2
C39—C45—H48109.5C167—C65—H66119.2
H46—C45—H48109.5C78—C80—H81109.5
H47—C45—H48109.5C78—C80—H82109.5
C2—C10—C16112.2 (2)H81—C80—H82109.5
C2—C10—C12110.1 (2)C78—C80—H83109.5
C16—C10—C12110.5 (2)H81—C80—H83109.5
C2—C10—H11108H82—C80—H83109.5
C16—C10—H11108C95—C98—H99109.5
C12—C10—H11108C95—C98—H100109.5
C39—C41—H42109.5H99—C98—H100109.5
C39—C41—H43109.5C95—C98—H101109.5
H42—C41—H43109.5H99—C98—H101109.5
C39—C41—H44109.5H100—C98—H101109.5
H42—C41—H44109.5C65—C167—C59117.7 (2)
H43—C41—H44109.5C65—C167—C78119.4 (2)
C20—C22—H23109.5C59—C167—C78122.9 (2)
C20—C22—H24109.5O112—C59—C167119.5 (2)
H23—C22—H24109.5O112—C59—C60118.9 (2)
C20—C22—H25109.5C167—C59—C60121.5 (2)
H23—C22—H25109.5C20—C26—H27109.5
H24—C22—H25109.5C20—C26—H28109.5
C36—C34—C32119.1 (2)H27—C26—H28109.5
C36—C34—H35120.5C20—C26—H29109.5
C32—C34—H35120.5H27—C26—H29109.5
C9—C20—C22110.1 (2)H28—C26—H29109.5
C9—C20—C26113.7 (2)C5—C7—C9121.3 (2)
C22—C20—C26109.8 (2)C5—C7—H8119.4
C9—C20—H21107.6C9—C7—H8119.4
C22—C20—H21107.6C68—C74—H75109.5
C26—C20—H21107.6C68—C74—H76109.5
C5—C3—C2121.3 (2)H75—C74—H76109.5
C5—C3—H4119.3C68—C74—H77109.5
C2—C3—H4119.3H75—C74—H77109.5
C78—C84—H85109.5H76—C74—H77109.5
C78—C84—H86109.5C61—C63—C65119.5 (2)
H85—C84—H86109.5C61—C63—H64120.3
C78—C84—H87109.5C65—C63—H64120.3
H85—C84—H87109.5N109—C102—C105112.4 (2)
H86—C84—H87109.5N109—C102—H103109.1
N109—C95—C98113.8 (2)C105—C102—H103109.1
N109—C95—H96108.8N109—C102—H104109.1
C98—C95—H96108.8C105—C102—H104109.1
N109—C95—H97108.8H103—C102—H104107.9
C98—C95—H97108.8C38—C49—C55112.4 (2)
H96—C95—H97107.7C38—C49—C51111.2 (2)
O111—C30—C31118.1 (2)C55—C49—C51108.7 (2)
O111—C30—C38120.1 (2)C38—C49—H50108.1
C31—C30—C38121.5 (2)C55—C49—H50108.1
C63—C61—C60121.8 (3)C51—C49—H50108.1
C63—C61—H62119.1C49—C55—H56109.5
C60—C61—H62119.1C49—C55—H57109.5
C31—C32—C34121.1 (2)H56—C55—H57109.5
C31—C32—H33119.4C49—C55—H58109.5
C34—C32—H33119.4H56—C55—H58109.5
C60—C68—C70112.2 (2)H57—C55—H58109.5
C60—C68—C74109.9 (2)C49—C51—H52109.5
C70—C68—C74110.3 (2)C49—C51—H53109.5
C60—C68—H69108.1H52—C51—H53109.5
C70—C68—H69108.1C49—C51—H54109.5
C74—C68—H69108.1H52—C51—H54109.5
C68—C70—H71109.5H53—C51—H54109.5
C68—C70—H72109.5
O111—Si1—O112—C5916.9 (2)C2—C1—C9—C20177.8 (2)
O110—Si1—O112—C5993.8 (2)C22—C20—C9—C788.2 (3)
S114—Si1—O112—C59143.58 (18)C26—C20—C9—C735.5 (3)
O111—Si1—O110—C1134.53 (17)C22—C20—C9—C189.6 (3)
O112—Si1—O110—C1118.80 (17)C26—C20—C9—C1146.7 (2)
S114—Si1—O110—C15.65 (18)C63—C61—C60—C590.3 (4)
O112—Si1—O111—C30166.1 (2)C63—C61—C60—C68177.7 (3)
O110—Si1—O111—C3055.4 (2)C70—C68—C60—C6157.9 (3)
S114—Si1—O111—C3069.7 (2)C74—C68—C60—C6165.2 (3)
Si1—O110—C1—C277.8 (2)C70—C68—C60—C59124.8 (2)
Si1—O110—C1—C9105.9 (2)C74—C68—C60—C59112.1 (3)
O110—C1—C2—C3176.8 (2)C32—C34—C36—C381.2 (4)
C9—C1—C2—C30.6 (3)C30—C38—C36—C340.3 (4)
O110—C1—C2—C100.8 (3)C49—C38—C36—C34179.3 (2)
C9—C1—C2—C10177.0 (2)C102—N109—C88—C9168.9 (3)
C32—C31—C39—C4131.0 (3)C95—N109—C88—C91162.5 (2)
C30—C31—C39—C41152.6 (2)C63—C65—C167—C590.8 (4)
C32—C31—C39—C4592.8 (3)C63—C65—C167—C78176.0 (2)
C30—C31—C39—C4583.6 (3)C80—C78—C167—C6554.6 (3)
C1—C2—C10—C16130.0 (2)C84—C78—C167—C6568.7 (3)
C3—C2—C10—C1652.5 (3)C80—C78—C167—C59128.7 (2)
C1—C2—C10—C12106.5 (2)C84—C78—C167—C59107.9 (3)
C3—C2—C10—C1271.0 (3)Si1—O112—C59—C16780.8 (3)
C7—C5—C3—C20.5 (4)Si1—O112—C59—C60103.3 (2)
C1—C2—C3—C50.9 (4)C65—C167—C59—O112177.6 (2)
C10—C2—C3—C5176.8 (2)C78—C167—C59—O1121.0 (3)
C102—N109—C95—C9859.1 (3)C65—C167—C59—C601.8 (3)
C88—N109—C95—C9868.6 (3)C78—C167—C59—C60174.8 (2)
Si1—O111—C30—C3195.5 (3)C61—C60—C59—O112177.2 (2)
Si1—O111—C30—C3890.0 (3)C68—C60—C59—O1120.2 (3)
C32—C31—C30—O111176.2 (2)C61—C60—C59—C1671.4 (3)
C39—C31—C30—O1110.4 (3)C68—C60—C59—C167176.0 (2)
C32—C31—C30—C381.7 (3)C3—C5—C7—C90.1 (4)
C39—C31—C30—C38174.8 (2)C1—C9—C7—C50.4 (3)
C36—C38—C30—O111175.6 (2)C20—C9—C7—C5177.4 (2)
C49—C38—C30—O1113.4 (3)C60—C61—C63—C651.3 (4)
C36—C38—C30—C311.2 (3)C167—C65—C63—C610.8 (4)
C49—C38—C30—C31177.8 (2)C88—N109—C102—C105174.0 (2)
C30—C31—C32—C340.7 (4)C95—N109—C102—C10559.1 (3)
C39—C31—C32—C34175.8 (2)C36—C38—C49—C5568.6 (3)
C36—C34—C32—C310.7 (4)C30—C38—C49—C55112.4 (3)
O110—C1—C9—C7176.2 (2)C36—C38—C49—C5153.6 (3)
C2—C1—C9—C70.1 (3)C30—C38—C49—C51125.4 (2)
O110—C1—C9—C205.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N109—H115···S1140.91 (3)2.19 (3)3.085 (2)168 (2)
(tdst_et3n_165) top
Crystal data top
C36H51O3SSi·C6H16NF(000) = 1520
Mr = 694.11Dx = 1.109 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3002 reflections
a = 11.6874 (11) Åθ = 3.1–29.2°
b = 17.9345 (12) ŵ = 0.14 mm1
c = 20.1975 (18) ÅT = 165 K
β = 100.976 (7)°Block, colourless
V = 4156.1 (6) Å30.34 × 0.22 × 0.13 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
7217 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.051
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.2°
rotation method scansh = 1414
21609 measured reflectionsk = 1922
8083 independent reflectionsl = 2424
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0485P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.34 e Å3
8083 reflectionsΔρmin = 0.20 e Å3
452 parametersAbsolute structure: Flack x determined using 3164 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 0.04 (4)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.55628 (5)0.26160 (3)0.06094 (3)0.01606 (15)
S1140.40836 (5)0.20896 (3)0.01656 (4)0.02412 (15)
O1120.54733 (15)0.35365 (9)0.05795 (10)0.0206 (4)
O1100.59247 (15)0.23911 (10)0.14231 (9)0.0199 (4)
O1110.67364 (16)0.24789 (9)0.02840 (9)0.0205 (4)
N1090.1976 (2)0.28351 (13)0.07467 (12)0.0252 (5)
H1150.265 (3)0.2655 (17)0.0509 (17)0.023 (8)*
C380.7318 (2)0.14388 (15)0.03335 (14)0.0235 (6)
C780.5840 (2)0.38520 (15)0.07808 (14)0.0255 (6)
H790.53910.3440.06390.031*
C10.5326 (2)0.19640 (14)0.18200 (13)0.0196 (5)
C50.4246 (3)0.11129 (16)0.26724 (15)0.0300 (6)
H60.38830.08290.29580.036*
C310.8570 (2)0.18988 (15)0.07029 (14)0.0239 (6)
C20.4386 (2)0.22656 (15)0.20650 (14)0.0221 (5)
C390.8813 (2)0.24747 (15)0.12710 (15)0.0258 (6)
H400.80690.26030.13970.031*
C450.9313 (3)0.31847 (18)0.10175 (18)0.0357 (7)
H461.00530.30760.08990.054*
H470.94130.35560.13660.054*
H480.87860.33680.06280.054*
C100.3950 (2)0.30569 (15)0.19143 (15)0.0251 (6)
H110.43310.32570.1560.03*
C410.9626 (3)0.2183 (2)0.19006 (17)0.0373 (7)
H420.93150.17290.20460.056*
H430.96930.25480.22530.056*
H441.03820.20880.17980.056*
C220.6252 (3)0.04929 (19)0.10534 (18)0.0422 (8)
H230.58680.00450.11540.063*
H240.68820.03670.08310.063*
H250.57050.08050.07640.063*
C340.9210 (3)0.08760 (16)0.00818 (17)0.0351 (7)
H350.97680.05190.00360.042*
C200.6728 (2)0.09073 (15)0.17070 (16)0.0274 (6)
H210.72060.13210.15960.033*
C30.3855 (2)0.18207 (16)0.24921 (14)0.0268 (6)
H40.32230.20090.26570.032*
C840.4980 (3)0.43940 (19)0.1193 (2)0.0416 (8)
H850.53910.48260.13030.062*
H860.4410.45430.09330.062*
H870.45970.41550.160.062*
C950.1072 (3)0.24983 (17)0.03928 (16)0.0318 (7)
H960.12490.2640.00790.038*
H970.11230.19590.04150.038*
C300.7522 (2)0.19229 (14)0.02247 (13)0.0202 (5)
C610.7631 (3)0.50339 (17)0.09670 (17)0.0352 (7)
H620.80070.53080.13360.042*
C320.9399 (2)0.13699 (17)0.06233 (16)0.0309 (6)
H331.00920.13450.09370.037*
C680.6586 (3)0.43474 (16)0.17673 (15)0.0299 (6)
H690.60560.3920.17430.036*
C700.7678 (3)0.4170 (2)0.22835 (17)0.0419 (8)
H710.80440.37330.21440.063*
H720.74710.4080.27140.063*
H730.82070.45830.23180.063*
C1050.2245 (4)0.39794 (19)0.00353 (18)0.0462 (9)
H1060.23730.45070.00540.069*
H1070.29270.37450.02190.069*
H1080.15920.38860.01780.069*
C90.5738 (2)0.12395 (14)0.19974 (13)0.0222 (5)
C910.2938 (3)0.2645 (2)0.17461 (19)0.0440 (8)
H920.2840.24050.21780.066*
H930.36030.24380.14510.066*
H940.30560.3170.17990.066*
C160.2631 (3)0.30832 (19)0.16559 (17)0.0368 (7)
H170.24210.27280.12980.055*
H180.24110.35740.1490.055*
H190.22360.29640.20180.055*
C600.6848 (3)0.44762 (14)0.10648 (15)0.0257 (6)
C360.8190 (3)0.09215 (16)0.03848 (16)0.0312 (6)
H370.80760.05950.07490.037*
C880.1868 (3)0.25254 (18)0.14500 (16)0.0348 (7)
H890.1710.19950.1440.042*
H900.12080.27590.1740.042*
C120.4294 (3)0.35498 (16)0.25414 (16)0.0320 (7)
H130.39240.33680.28950.048*
H140.40490.40530.24330.048*
H150.51250.35370.26890.048*
C650.7296 (3)0.47926 (17)0.02151 (16)0.0343 (7)
H660.74510.49020.06390.041*
C800.6650 (3)0.3527 (2)0.12175 (19)0.0446 (8)
H810.61980.32630.15910.067*
H820.71910.3190.09530.067*
H830.70710.39240.13830.067*
C980.0164 (3)0.2734 (2)0.06883 (18)0.0422 (8)
H990.03210.26430.11650.063*
H1000.02550.32560.06060.063*
H1010.06990.24530.04810.063*
C1670.6496 (2)0.42314 (15)0.01512 (14)0.0246 (6)
C590.6297 (2)0.40713 (14)0.04985 (14)0.0214 (5)
C260.7519 (3)0.0395 (2)0.2193 (2)0.0464 (9)
H270.7110.00580.22510.07*
H280.77430.06390.26210.07*
H290.82030.0280.20140.07*
C70.5184 (3)0.08234 (16)0.24268 (14)0.0274 (6)
H80.54480.03450.25510.033*
C740.5968 (3)0.5028 (2)0.19881 (18)0.0456 (8)
H750.58140.49450.24320.068*
H760.52460.51070.16790.068*
H770.64550.54590.19920.068*
C630.7863 (3)0.51895 (18)0.03372 (17)0.0395 (8)
H640.83980.55590.02850.047*
C1020.1998 (3)0.36665 (17)0.07408 (16)0.0340 (7)
H1030.12510.38530.09760.041*
H1040.25910.38390.09810.041*
C490.6219 (3)0.14621 (16)0.08751 (15)0.0272 (6)
H500.57620.18980.07910.033*
C550.5460 (3)0.07686 (18)0.08677 (18)0.0378 (7)
H560.58820.03360.09660.057*
H570.47610.0820.12020.057*
H580.52610.07150.04310.057*
C510.6522 (3)0.1547 (2)0.15820 (17)0.0410 (8)
H520.70050.19790.15890.062*
H530.58180.16030.19110.062*
H540.69330.11120.16850.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0148 (3)0.0161 (3)0.0177 (4)0.0002 (3)0.0041 (3)0.0002 (3)
S1140.0194 (3)0.0204 (3)0.0302 (4)0.0033 (3)0.0009 (3)0.0005 (3)
O1120.0193 (8)0.0184 (8)0.0247 (10)0.0012 (7)0.0058 (7)0.0003 (8)
O1100.0181 (8)0.0226 (9)0.0195 (10)0.0008 (7)0.0051 (7)0.0027 (7)
O1110.0204 (9)0.0208 (9)0.0221 (10)0.0017 (7)0.0082 (8)0.0004 (7)
N1090.0226 (12)0.0296 (12)0.0222 (13)0.0004 (10)0.0014 (10)0.0025 (9)
C380.0246 (13)0.0244 (13)0.0224 (14)0.0005 (10)0.0067 (12)0.0012 (11)
C780.0295 (14)0.0260 (14)0.0218 (14)0.0037 (11)0.0070 (12)0.0014 (11)
C10.0188 (12)0.0241 (13)0.0152 (13)0.0032 (10)0.0017 (10)0.0003 (10)
C50.0392 (16)0.0298 (14)0.0230 (15)0.0087 (12)0.0110 (13)0.0009 (11)
C310.0231 (13)0.0257 (13)0.0243 (14)0.0006 (10)0.0078 (12)0.0023 (10)
C20.0203 (12)0.0272 (14)0.0183 (14)0.0019 (10)0.0023 (11)0.0006 (10)
C390.0197 (13)0.0317 (16)0.0262 (15)0.0008 (11)0.0052 (12)0.0053 (11)
C450.0306 (15)0.0373 (16)0.0402 (19)0.0062 (13)0.0092 (14)0.0088 (13)
C100.0224 (13)0.0304 (15)0.0245 (15)0.0048 (11)0.0098 (12)0.0040 (11)
C410.0313 (16)0.0521 (19)0.0265 (17)0.0053 (14)0.0003 (14)0.0045 (14)
C220.049 (2)0.0440 (18)0.0345 (19)0.0098 (15)0.0105 (16)0.0087 (14)
C340.0351 (16)0.0293 (15)0.0410 (19)0.0127 (13)0.0075 (14)0.0031 (13)
C200.0271 (13)0.0218 (13)0.0343 (16)0.0031 (11)0.0084 (13)0.0031 (11)
C30.0267 (14)0.0332 (15)0.0226 (15)0.0037 (11)0.0101 (12)0.0027 (11)
C840.0374 (17)0.0404 (17)0.043 (2)0.0016 (14)0.0026 (16)0.0007 (15)
C950.0293 (15)0.0413 (18)0.0253 (16)0.0039 (12)0.0067 (13)0.0071 (13)
C300.0199 (12)0.0196 (12)0.0228 (14)0.0016 (9)0.0083 (11)0.0019 (10)
C610.0388 (17)0.0304 (15)0.0340 (18)0.0125 (13)0.0013 (14)0.0046 (12)
C320.0222 (14)0.0351 (15)0.0336 (18)0.0058 (12)0.0010 (13)0.0023 (13)
C680.0377 (16)0.0274 (14)0.0248 (16)0.0080 (12)0.0066 (13)0.0043 (11)
C700.052 (2)0.0402 (18)0.0320 (18)0.0016 (15)0.0048 (16)0.0045 (14)
C1050.069 (2)0.0330 (17)0.0370 (19)0.0062 (16)0.0113 (19)0.0032 (14)
C90.0238 (13)0.0234 (13)0.0182 (14)0.0034 (10)0.0012 (11)0.0019 (10)
C910.051 (2)0.050 (2)0.0352 (19)0.0044 (16)0.0190 (17)0.0098 (15)
C160.0256 (15)0.052 (2)0.0330 (18)0.0080 (13)0.0051 (14)0.0037 (14)
C600.0296 (14)0.0211 (13)0.0260 (15)0.0041 (11)0.0046 (12)0.0013 (11)
C360.0348 (16)0.0247 (14)0.0344 (17)0.0049 (12)0.0073 (14)0.0069 (12)
C880.0367 (17)0.0413 (17)0.0259 (16)0.0034 (13)0.0046 (14)0.0058 (13)
C120.0346 (16)0.0279 (15)0.0335 (17)0.0064 (12)0.0063 (14)0.0003 (12)
C650.0398 (17)0.0336 (16)0.0306 (17)0.0101 (13)0.0098 (14)0.0059 (13)
C800.0429 (19)0.053 (2)0.040 (2)0.0011 (16)0.0128 (17)0.0131 (16)
C980.0259 (15)0.069 (2)0.0321 (18)0.0019 (15)0.0056 (14)0.0089 (16)
C1670.0252 (13)0.0235 (14)0.0254 (15)0.0012 (10)0.0056 (12)0.0015 (11)
C590.0201 (12)0.0160 (12)0.0283 (15)0.0009 (10)0.0055 (11)0.0031 (10)
C260.0403 (18)0.048 (2)0.048 (2)0.0164 (16)0.0010 (17)0.0036 (16)
C70.0367 (15)0.0216 (13)0.0234 (15)0.0039 (11)0.0045 (13)0.0032 (10)
C740.055 (2)0.0456 (19)0.039 (2)0.0113 (16)0.0156 (18)0.0002 (16)
C630.0423 (17)0.0317 (16)0.045 (2)0.0191 (14)0.0092 (16)0.0023 (14)
C1020.0412 (17)0.0304 (15)0.0315 (17)0.0023 (13)0.0098 (14)0.0034 (12)
C490.0294 (14)0.0292 (15)0.0225 (15)0.0053 (11)0.0035 (12)0.0043 (11)
C550.0387 (17)0.0398 (18)0.0318 (18)0.0038 (14)0.0008 (15)0.0067 (14)
C510.053 (2)0.0464 (19)0.0240 (17)0.0122 (16)0.0089 (15)0.0018 (14)
Geometric parameters (Å, º) top
Si1—O1111.6485 (18)C61—C601.395 (4)
Si1—O1121.6546 (17)C61—H620.93
Si1—O1101.6665 (19)C32—H330.93
Si1—S1142.0231 (9)C68—C701.520 (5)
O112—C591.390 (3)C68—C601.525 (4)
O110—C11.390 (3)C68—C741.527 (4)
O111—C301.376 (3)C68—H690.98
N109—C1021.491 (4)C70—H710.96
N109—C881.508 (4)C70—H720.96
N109—C951.510 (4)C70—H730.96
N109—H1150.90 (4)C105—C1021.507 (5)
C38—C361.397 (4)C105—H1060.96
C38—C301.407 (4)C105—H1070.96
C38—C491.521 (4)C105—H1080.96
C78—C1671.516 (4)C9—C71.394 (4)
C78—C841.526 (4)C91—C881.502 (5)
C78—C801.527 (4)C91—H920.96
C78—H790.98C91—H930.96
C1—C21.397 (4)C91—H940.96
C1—C91.408 (4)C16—H170.96
C5—C31.375 (4)C16—H180.96
C5—C71.388 (4)C16—H190.96
C5—H60.93C60—C591.404 (4)
C31—C321.387 (4)C36—H370.93
C31—C301.408 (4)C88—H890.97
C31—C391.530 (4)C88—H900.97
C2—C31.404 (4)C12—H130.96
C2—C101.519 (4)C12—H140.96
C39—C411.527 (5)C12—H150.96
C39—C451.529 (4)C65—C631.382 (5)
C39—H400.98C65—C1671.397 (4)
C45—H460.96C65—H660.93
C45—H470.96C80—H810.96
C45—H480.96C80—H820.96
C10—C161.531 (4)C80—H830.96
C10—C121.534 (4)C98—H990.96
C10—H110.98C98—H1000.96
C41—H420.96C98—H1010.96
C41—H430.96C167—C591.405 (4)
C41—H440.96C26—H270.96
C22—C201.525 (5)C26—H280.96
C22—H230.96C26—H290.96
C22—H240.96C7—H80.93
C22—H250.96C74—H750.96
C34—C361.374 (5)C74—H760.96
C34—C321.392 (4)C74—H770.96
C34—H350.93C63—H640.93
C20—C91.515 (4)C102—H1030.97
C20—C261.522 (4)C102—H1040.97
C20—H210.98C49—C551.529 (4)
C3—H40.93C49—C511.543 (4)
C84—H850.96C49—H500.98
C84—H860.96C55—H560.96
C84—H870.96C55—H570.96
C95—C981.514 (4)C55—H580.96
C95—H960.97C51—H520.96
C95—H970.97C51—H530.96
C61—C631.379 (5)C51—H540.96
O111—Si1—O112100.71 (9)H71—C70—H72109.5
O111—Si1—O110106.43 (9)C68—C70—H73109.5
O112—Si1—O110106.25 (10)H71—C70—H73109.5
O111—Si1—S114117.35 (8)H72—C70—H73109.5
O112—Si1—S114114.00 (8)C102—C105—H106109.5
O110—Si1—S114111.04 (7)C102—C105—H107109.5
C59—O112—Si1130.72 (16)H106—C105—H107109.5
C1—O110—Si1129.86 (16)C102—C105—H108109.5
C30—O111—Si1139.68 (16)H106—C105—H108109.5
C102—N109—C88112.0 (2)H107—C105—H108109.5
C102—N109—C95114.1 (2)C7—C9—C1118.4 (2)
C88—N109—C95110.9 (2)C7—C9—C20120.6 (2)
C102—N109—H115110 (2)C1—C9—C20120.9 (2)
C88—N109—H115106 (2)C88—C91—H92109.5
C95—N109—H115103 (2)C88—C91—H93109.5
C36—C38—C30117.0 (3)H92—C91—H93109.5
C36—C38—C49119.5 (2)C88—C91—H94109.5
C30—C38—C49123.4 (2)H92—C91—H94109.5
C167—C78—C84110.3 (2)H93—C91—H94109.5
C167—C78—C80112.7 (2)C10—C16—H17109.5
C84—C78—C80110.2 (3)C10—C16—H18109.5
C167—C78—H79107.8H17—C16—H18109.5
C84—C78—H79107.8C10—C16—H19109.5
C80—C78—H79107.8H17—C16—H19109.5
O110—C1—C2120.5 (2)H18—C16—H19109.5
O110—C1—C9118.0 (2)C61—C60—C59117.8 (3)
C2—C1—C9121.4 (2)C61—C60—C68119.6 (3)
C3—C5—C7119.8 (3)C59—C60—C68122.5 (2)
C3—C5—H6120.1C34—C36—C38122.6 (3)
C7—C5—H6120.1C34—C36—H37118.7
C32—C31—C30118.5 (3)C38—C36—H37118.7
C32—C31—C39120.9 (3)C91—C88—N109113.3 (3)
C30—C31—C39120.5 (2)C91—C88—H89108.9
C1—C2—C3117.9 (2)N109—C88—H89108.9
C1—C2—C10123.2 (2)C91—C88—H90108.9
C3—C2—C10118.9 (2)N109—C88—H90108.9
C41—C39—C45110.3 (2)H89—C88—H90107.7
C41—C39—C31113.0 (2)C10—C12—H13109.5
C45—C39—C31109.8 (2)C10—C12—H14109.5
C41—C39—H40107.8H13—C12—H14109.5
C45—C39—H40107.8C10—C12—H15109.5
C31—C39—H40107.8H13—C12—H15109.5
C39—C45—H46109.5H14—C12—H15109.5
C39—C45—H47109.5C63—C65—C167121.6 (3)
H46—C45—H47109.5C63—C65—H66119.2
C39—C45—H48109.5C167—C65—H66119.2
H46—C45—H48109.5C78—C80—H81109.5
H47—C45—H48109.5C78—C80—H82109.5
C2—C10—C16112.0 (2)H81—C80—H82109.5
C2—C10—C12110.4 (2)C78—C80—H83109.5
C16—C10—C12110.6 (2)H81—C80—H83109.5
C2—C10—H11107.9H82—C80—H83109.5
C16—C10—H11107.9C95—C98—H99109.5
C12—C10—H11107.9C95—C98—H100109.5
C39—C41—H42109.5H99—C98—H100109.5
C39—C41—H43109.5C95—C98—H101109.5
H42—C41—H43109.5H99—C98—H101109.5
C39—C41—H44109.5H100—C98—H101109.5
H42—C41—H44109.5C65—C167—C59117.8 (3)
H43—C41—H44109.5C65—C167—C78119.1 (2)
C20—C22—H23109.5C59—C167—C78123.0 (2)
C20—C22—H24109.5O112—C59—C60118.8 (2)
H23—C22—H24109.5O112—C59—C167119.5 (2)
C20—C22—H25109.5C60—C59—C167121.6 (2)
H23—C22—H25109.5C20—C26—H27109.5
H24—C22—H25109.5C20—C26—H28109.5
C36—C34—C32119.2 (3)H27—C26—H28109.5
C36—C34—H35120.4C20—C26—H29109.5
C32—C34—H35120.4H27—C26—H29109.5
C9—C20—C26113.7 (3)H28—C26—H29109.5
C9—C20—C22110.3 (2)C5—C7—C9121.0 (3)
C26—C20—C22109.9 (3)C5—C7—H8119.5
C9—C20—H21107.5C9—C7—H8119.5
C26—C20—H21107.5C68—C74—H75109.5
C22—C20—H21107.5C68—C74—H76109.5
C5—C3—C2121.6 (3)H75—C74—H76109.5
C5—C3—H4119.2C68—C74—H77109.5
C2—C3—H4119.2H75—C74—H77109.5
C78—C84—H85109.5H76—C74—H77109.5
C78—C84—H86109.5C61—C63—C65119.5 (3)
H85—C84—H86109.5C61—C63—H64120.3
C78—C84—H87109.5C65—C63—H64120.3
H85—C84—H87109.5N109—C102—C105112.3 (3)
H86—C84—H87109.5N109—C102—H103109.1
N109—C95—C98113.7 (2)C105—C102—H103109.1
N109—C95—H96108.8N109—C102—H104109.1
C98—C95—H96108.8C105—C102—H104109.1
N109—C95—H97108.8H103—C102—H104107.9
C98—C95—H97108.8C38—C49—C55112.5 (2)
H96—C95—H97107.7C38—C49—C51110.9 (3)
O111—C30—C38120.2 (2)C55—C49—C51109.0 (3)
O111—C30—C31118.0 (2)C38—C49—H50108.1
C38—C30—C31121.6 (2)C55—C49—H50108.1
C63—C61—C60121.7 (3)C51—C49—H50108.1
C63—C61—H62119.1C49—C55—H56109.5
C60—C61—H62119.1C49—C55—H57109.5
C31—C32—C34121.1 (3)H56—C55—H57109.5
C31—C32—H33119.4C49—C55—H58109.5
C34—C32—H33119.4H56—C55—H58109.5
C70—C68—C60112.3 (3)H57—C55—H58109.5
C70—C68—C74110.4 (3)C49—C51—H52109.5
C60—C68—C74109.9 (2)C49—C51—H53109.5
C70—C68—H69108H52—C51—H53109.5
C60—C68—H69108C49—C51—H54109.5
C74—C68—H69108H52—C51—H54109.5
C68—C70—H71109.5H53—C51—H54109.5
C68—C70—H72109.5
O111—Si1—O112—C5916.9 (2)C2—C1—C9—C20177.6 (3)
O110—Si1—O112—C5993.9 (2)C26—C20—C9—C736.6 (4)
S114—Si1—O112—C59143.5 (2)C22—C20—C9—C787.5 (3)
O111—Si1—O110—C1134.4 (2)C26—C20—C9—C1145.9 (3)
O112—Si1—O110—C1118.9 (2)C22—C20—C9—C190.0 (3)
S114—Si1—O110—C15.6 (2)C63—C61—C60—C590.2 (5)
O112—Si1—O111—C30165.9 (3)C63—C61—C60—C68177.6 (3)
O110—Si1—O111—C3055.3 (3)C70—C68—C60—C6157.9 (4)
S114—Si1—O111—C3069.8 (3)C74—C68—C60—C6165.5 (4)
Si1—O110—C1—C277.9 (3)C70—C68—C60—C59124.5 (3)
Si1—O110—C1—C9105.7 (2)C74—C68—C60—C59112.2 (3)
O110—C1—C2—C3176.7 (2)C32—C34—C36—C381.0 (5)
C9—C1—C2—C30.4 (4)C30—C38—C36—C340.0 (4)
O110—C1—C2—C100.7 (4)C49—C38—C36—C34179.2 (3)
C9—C1—C2—C10176.9 (3)C102—N109—C88—C9169.2 (3)
C32—C31—C39—C4131.1 (4)C95—N109—C88—C91162.0 (3)
C30—C31—C39—C41152.7 (3)C63—C65—C167—C591.1 (5)
C32—C31—C39—C4592.6 (3)C63—C65—C167—C78175.8 (3)
C30—C31—C39—C4583.6 (3)C84—C78—C167—C6568.9 (3)
C1—C2—C10—C16129.6 (3)C80—C78—C167—C6554.7 (4)
C3—C2—C10—C1653.0 (3)C84—C78—C167—C59107.8 (3)
C1—C2—C10—C12106.7 (3)C80—C78—C167—C59128.6 (3)
C3—C2—C10—C1270.7 (3)Si1—O112—C59—C60103.6 (3)
C7—C5—C3—C20.3 (4)Si1—O112—C59—C16780.9 (3)
C1—C2—C3—C50.6 (4)C61—C60—C59—O112177.1 (3)
C10—C2—C3—C5176.9 (3)C68—C60—C59—O1120.6 (4)
C102—N109—C95—C9859.2 (4)C61—C60—C59—C1671.8 (4)
C88—N109—C95—C9868.4 (3)C68—C60—C59—C167175.9 (3)
Si1—O111—C30—C3890.1 (3)C65—C167—C59—O112177.5 (2)
Si1—O111—C30—C3195.4 (3)C78—C167—C59—O1120.8 (4)
C36—C38—C30—O111175.7 (2)C65—C167—C59—C602.2 (4)
C49—C38—C30—O1113.5 (4)C78—C167—C59—C60174.5 (3)
C36—C38—C30—C311.4 (4)C3—C5—C7—C90.1 (4)
C49—C38—C30—C31177.8 (2)C1—C9—C7—C50.3 (4)
C32—C31—C30—O111176.0 (2)C20—C9—C7—C5177.3 (3)
C39—C31—C30—O1110.3 (4)C60—C61—C63—C650.9 (5)
C32—C31—C30—C381.6 (4)C167—C65—C63—C610.5 (5)
C39—C31—C30—C38174.7 (2)C88—N109—C102—C105173.4 (3)
C30—C31—C32—C340.5 (4)C95—N109—C102—C10559.5 (4)
C39—C31—C32—C34175.8 (3)C36—C38—C49—C5568.5 (3)
C36—C34—C32—C310.8 (5)C30—C38—C49—C55112.4 (3)
O110—C1—C9—C7176.4 (2)C36—C38—C49—C5153.9 (4)
C2—C1—C9—C70.0 (4)C30—C38—C49—C51125.2 (3)
O110—C1—C9—C206.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N109—H115···S1140.90 (4)2.19 (4)3.086 (3)169 (3)
(tdst_et3n_180) top
Crystal data top
C36H51O3SSi·C6H16NF(000) = 1520
Mr = 694.11Dx = 1.107 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2579 reflections
a = 11.7030 (12) Åθ = 3.1–29.4°
b = 17.9455 (13) ŵ = 0.14 mm1
c = 20.2104 (19) ÅT = 180 K
β = 101.001 (8)°Block, colourless
V = 4166.5 (7) Å30.34 × 0.22 × 0.13 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
7008 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.053
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.2°
rotation method scansh = 1414
20391 measured reflectionsk = 1922
7996 independent reflectionsl = 2424
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0471P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.28 e Å3
7996 reflectionsΔρmin = 0.18 e Å3
452 parametersAbsolute structure: Flack x determined using 3042 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 0.02 (4)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.55632 (5)0.26175 (4)0.06094 (4)0.01747 (15)
S1140.40862 (6)0.20915 (4)0.01665 (4)0.02615 (16)
O1120.54750 (16)0.35373 (9)0.05785 (10)0.0220 (4)
O1100.59240 (15)0.23942 (10)0.14228 (9)0.0214 (4)
O1110.67359 (16)0.24802 (10)0.02831 (10)0.0223 (4)
N1090.1976 (2)0.28338 (14)0.07437 (13)0.0282 (5)
H1150.265 (3)0.2656 (16)0.0512 (16)0.017 (7)*
C380.7314 (2)0.14413 (15)0.03299 (15)0.0255 (6)
C780.5838 (3)0.38514 (16)0.07811 (15)0.0282 (6)
H790.53910.34390.06390.034*
C10.5327 (2)0.19667 (14)0.18188 (13)0.0210 (5)
C50.4249 (3)0.11152 (17)0.26696 (16)0.0329 (7)
H60.38870.0830.29540.039*
C310.8564 (2)0.19032 (16)0.07033 (15)0.0259 (6)
C20.4388 (2)0.22663 (15)0.20639 (14)0.0243 (6)
C390.8811 (2)0.24776 (16)0.12708 (16)0.0288 (6)
H400.80680.26060.13970.035*
C450.9309 (3)0.31891 (18)0.10153 (19)0.0383 (7)
H461.00480.30810.08960.057*
H470.9410.35610.13630.057*
H480.87810.33710.06260.057*
C100.3953 (2)0.30564 (16)0.19133 (15)0.0273 (6)
H110.43340.32570.1560.033*
C410.9621 (3)0.2190 (2)0.18988 (18)0.0413 (8)
H420.93140.17350.20440.062*
H430.96820.25560.22510.062*
H441.03770.20980.17980.062*
C220.6245 (3)0.0487 (2)0.10569 (19)0.0474 (9)
H230.5840.00510.11610.071*
H240.68750.03430.08420.071*
H250.57170.08030.07590.071*
C340.9205 (3)0.08789 (17)0.00836 (18)0.0381 (7)
H350.97640.05240.00380.046*
C200.6723 (3)0.09078 (15)0.17032 (16)0.0293 (6)
H210.71930.13210.15850.035*
C30.3857 (2)0.18219 (17)0.24927 (15)0.0292 (6)
H40.32280.20110.2660.035*
C840.4982 (3)0.4393 (2)0.1193 (2)0.0460 (8)
H850.53940.48230.13040.069*
H860.44130.45420.09340.069*
H870.45990.41530.160.069*
C950.1072 (3)0.24943 (18)0.03943 (17)0.0350 (7)
H960.12440.26350.00780.042*
H970.11250.19560.04170.042*
C300.7521 (2)0.19247 (14)0.02268 (14)0.0221 (6)
C610.7623 (3)0.50374 (18)0.09641 (18)0.0389 (8)
H620.79980.53120.13330.047*
C320.9390 (3)0.13732 (17)0.06262 (16)0.0335 (7)
H331.00790.13460.09420.04*
C680.6578 (3)0.43506 (17)0.17623 (16)0.0329 (7)
H690.60490.39240.17390.04*
C700.7669 (3)0.4176 (2)0.22819 (19)0.0468 (9)
H710.80380.3740.21450.07*
H720.7460.40890.27120.07*
H730.81960.4590.23160.07*
C1050.2251 (4)0.3978 (2)0.0037 (2)0.0517 (10)
H1060.23920.45040.00570.078*
H1070.29250.37390.02210.078*
H1080.15940.38940.01740.078*
C90.5738 (2)0.12421 (15)0.19941 (14)0.0240 (6)
C910.2945 (4)0.2637 (2)0.1740 (2)0.0489 (9)
H920.28610.23810.21630.073*
H930.36090.24430.14340.073*
H940.30530.31590.18080.073*
C160.2636 (3)0.3082 (2)0.16539 (18)0.0410 (8)
H170.24240.27150.13060.061*
H180.24190.35680.14740.061*
H190.2240.29790.20180.061*
C600.6841 (3)0.44782 (14)0.10624 (16)0.0276 (6)
C360.8190 (3)0.09230 (17)0.03809 (17)0.0342 (7)
H370.80770.05960.07450.041*
C880.1869 (3)0.25213 (19)0.14472 (17)0.0387 (8)
H890.17070.19920.14370.046*
H900.12140.27570.17390.046*
C120.4290 (3)0.35503 (17)0.25402 (17)0.0355 (7)
H130.39190.33680.28920.053*
H140.40440.40530.2430.053*
H150.5120.35390.2690.053*
C650.7288 (3)0.47959 (18)0.02156 (17)0.0370 (7)
H660.74410.49070.0640.044*
C800.6646 (3)0.3530 (2)0.1215 (2)0.0491 (9)
H810.61970.32580.15850.074*
H820.71960.320.09480.074*
H830.70550.39270.13860.074*
C980.0158 (3)0.2728 (2)0.0691 (2)0.0483 (9)
H990.03180.26260.11660.072*
H1000.02470.32510.06190.072*
H1010.06930.24540.04780.072*
C1670.6491 (2)0.42328 (15)0.01527 (15)0.0263 (6)
C590.6293 (2)0.40719 (14)0.04964 (15)0.0228 (6)
C260.7528 (3)0.0406 (2)0.2192 (2)0.0518 (10)
H270.71190.00390.22710.078*
H280.7780.06640.2610.078*
H290.81930.02760.20020.078*
C70.5184 (3)0.08276 (16)0.24241 (15)0.0306 (6)
H80.54470.03490.25480.037*
C740.5966 (4)0.5028 (2)0.1984 (2)0.0519 (10)
H750.58020.49420.24250.078*
H760.52510.51130.16710.078*
H770.6460.54570.19950.078*
C630.7854 (3)0.51912 (19)0.03358 (18)0.0428 (8)
H640.83880.5560.02830.051*
C1020.2003 (3)0.36622 (18)0.07404 (17)0.0381 (7)
H1030.12580.38490.09770.046*
H1040.25960.38320.09810.046*
C490.6222 (3)0.14619 (16)0.08721 (15)0.0299 (6)
H500.57620.18960.07880.036*
C550.5465 (3)0.07691 (19)0.08671 (19)0.0422 (8)
H560.58940.03360.09540.063*
H570.47770.08150.1210.063*
H580.52470.07210.04340.063*
C510.6524 (4)0.1550 (2)0.15779 (18)0.0456 (8)
H520.7010.1980.15830.068*
H530.58210.1610.19060.068*
H540.69310.11150.16830.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0163 (3)0.0178 (3)0.0188 (4)0.0003 (3)0.0046 (3)0.0001 (3)
S1140.0208 (3)0.0225 (3)0.0328 (4)0.0040 (3)0.0008 (3)0.0002 (3)
O1120.0206 (9)0.0209 (9)0.0250 (10)0.0025 (8)0.0057 (8)0.0003 (8)
O1100.0200 (9)0.0237 (9)0.0210 (10)0.0009 (7)0.0052 (8)0.0029 (7)
O1110.0211 (9)0.0223 (9)0.0250 (11)0.0019 (7)0.0085 (8)0.0004 (7)
N1090.0243 (12)0.0347 (14)0.0246 (14)0.0008 (10)0.0019 (11)0.0039 (10)
C380.0281 (14)0.0243 (13)0.0251 (15)0.0005 (11)0.0076 (12)0.0014 (11)
C780.0328 (15)0.0270 (14)0.0259 (16)0.0049 (12)0.0080 (13)0.0020 (11)
C10.0203 (12)0.0258 (13)0.0165 (13)0.0041 (10)0.0023 (11)0.0004 (10)
C50.0427 (17)0.0325 (15)0.0264 (16)0.0105 (13)0.0140 (14)0.0015 (12)
C310.0240 (13)0.0296 (14)0.0255 (15)0.0003 (11)0.0083 (12)0.0022 (11)
C20.0228 (13)0.0303 (14)0.0191 (14)0.0027 (11)0.0026 (12)0.0013 (11)
C390.0210 (13)0.0370 (17)0.0290 (16)0.0022 (11)0.0060 (12)0.0054 (12)
C450.0316 (15)0.0375 (17)0.047 (2)0.0060 (13)0.0097 (15)0.0093 (14)
C100.0241 (14)0.0344 (16)0.0254 (16)0.0054 (11)0.0101 (12)0.0043 (12)
C410.0342 (17)0.058 (2)0.0296 (18)0.0056 (15)0.0000 (15)0.0065 (15)
C220.056 (2)0.049 (2)0.040 (2)0.0117 (17)0.0139 (18)0.0094 (16)
C340.0366 (17)0.0347 (16)0.043 (2)0.0146 (14)0.0072 (15)0.0039 (14)
C200.0287 (14)0.0230 (14)0.0371 (18)0.0030 (11)0.0086 (13)0.0031 (12)
C30.0277 (14)0.0378 (16)0.0245 (16)0.0046 (12)0.0107 (13)0.0026 (12)
C840.0409 (18)0.0453 (19)0.048 (2)0.0030 (15)0.0021 (17)0.0006 (16)
C950.0310 (16)0.0457 (19)0.0284 (18)0.0037 (13)0.0057 (14)0.0092 (13)
C300.0217 (13)0.0215 (13)0.0247 (15)0.0011 (10)0.0088 (12)0.0020 (10)
C610.0458 (18)0.0309 (16)0.038 (2)0.0157 (14)0.0033 (16)0.0055 (13)
C320.0241 (14)0.0397 (16)0.0345 (19)0.0081 (12)0.0001 (14)0.0027 (13)
C680.0415 (17)0.0301 (15)0.0269 (17)0.0097 (13)0.0057 (14)0.0050 (12)
C700.057 (2)0.045 (2)0.037 (2)0.0013 (17)0.0060 (18)0.0048 (15)
C1050.077 (3)0.0365 (18)0.041 (2)0.0089 (18)0.011 (2)0.0052 (15)
C90.0264 (13)0.0243 (13)0.0198 (15)0.0034 (11)0.0008 (12)0.0019 (11)
C910.057 (2)0.056 (2)0.039 (2)0.0051 (17)0.0209 (18)0.0114 (16)
C160.0272 (16)0.058 (2)0.038 (2)0.0082 (14)0.0047 (15)0.0039 (16)
C600.0298 (14)0.0242 (13)0.0283 (16)0.0045 (12)0.0043 (12)0.0016 (11)
C360.0379 (17)0.0274 (15)0.0380 (19)0.0061 (12)0.0087 (15)0.0080 (12)
C880.0398 (18)0.0476 (19)0.0277 (18)0.0060 (14)0.0041 (15)0.0057 (14)
C120.0379 (17)0.0316 (16)0.0369 (19)0.0078 (13)0.0069 (15)0.0005 (13)
C650.0417 (18)0.0355 (17)0.0348 (19)0.0105 (14)0.0097 (15)0.0063 (13)
C800.048 (2)0.058 (2)0.043 (2)0.0005 (17)0.0146 (18)0.0134 (17)
C980.0294 (16)0.080 (3)0.035 (2)0.0020 (17)0.0047 (15)0.0112 (18)
C1670.0281 (14)0.0222 (14)0.0295 (16)0.0013 (11)0.0075 (13)0.0010 (11)
C590.0203 (12)0.0175 (12)0.0302 (16)0.0018 (10)0.0041 (12)0.0021 (11)
C260.044 (2)0.052 (2)0.056 (3)0.0195 (17)0.0023 (19)0.0047 (18)
C70.0398 (16)0.0234 (14)0.0280 (17)0.0034 (12)0.0047 (14)0.0022 (11)
C740.062 (2)0.054 (2)0.042 (2)0.0148 (18)0.016 (2)0.0015 (17)
C630.0457 (19)0.0348 (17)0.049 (2)0.0199 (14)0.0125 (17)0.0027 (15)
C1020.0464 (18)0.0339 (16)0.0358 (19)0.0016 (14)0.0121 (16)0.0015 (13)
C490.0326 (15)0.0329 (16)0.0236 (16)0.0054 (12)0.0040 (13)0.0031 (12)
C550.0428 (18)0.0429 (19)0.038 (2)0.0051 (15)0.0004 (16)0.0058 (15)
C510.058 (2)0.052 (2)0.0282 (19)0.0131 (17)0.0112 (17)0.0007 (15)
Geometric parameters (Å, º) top
Si1—O1111.6507 (18)C61—C601.398 (4)
Si1—O1121.6542 (18)C61—H620.93
Si1—O1101.6664 (19)C32—H330.93
Si1—S1142.0222 (10)C68—C601.521 (4)
O112—C591.388 (3)C68—C741.521 (5)
O110—C11.390 (3)C68—C701.523 (5)
O111—C301.375 (3)C68—H690.98
N109—C1021.487 (4)C70—H710.96
N109—C951.508 (4)C70—H720.96
N109—C881.511 (4)C70—H730.96
N109—H1150.90 (3)C105—C1021.507 (5)
C38—C361.402 (4)C105—H1060.96
C38—C301.405 (4)C105—H1070.96
C38—C491.517 (4)C105—H1080.96
C78—C1671.515 (4)C9—C71.394 (4)
C78—C801.521 (4)C91—C881.504 (5)
C78—C841.524 (5)C91—H920.96
C78—H790.98C91—H930.96
C1—C21.396 (4)C91—H940.96
C1—C91.408 (4)C16—H170.96
C5—C31.373 (4)C16—H180.96
C5—C71.385 (4)C16—H190.96
C5—H60.93C60—C591.404 (4)
C31—C321.385 (4)C36—H370.93
C31—C301.404 (4)C88—H890.97
C31—C391.528 (4)C88—H900.97
C2—C31.407 (4)C12—H130.96
C2—C101.518 (4)C12—H140.96
C39—C411.522 (5)C12—H150.96
C39—C451.533 (4)C65—C631.379 (5)
C39—H400.98C65—C1671.398 (4)
C45—H460.96C65—H660.93
C45—H470.96C80—H810.96
C45—H480.96C80—H820.96
C10—C161.531 (4)C80—H830.96
C10—C121.535 (4)C98—H990.96
C10—H110.98C98—H1000.96
C41—H420.96C98—H1010.96
C41—H430.96C167—C591.405 (4)
C41—H440.96C26—H270.96
C22—C201.520 (5)C26—H280.96
C22—H230.96C26—H290.96
C22—H240.96C7—H80.93
C22—H250.96C74—H750.96
C34—C361.368 (5)C74—H760.96
C34—C321.395 (5)C74—H770.96
C34—H350.93C63—H640.93
C20—C91.514 (4)C102—H1030.97
C20—C261.523 (5)C102—H1040.97
C20—H210.98C49—C551.528 (4)
C3—H40.93C49—C511.542 (4)
C84—H850.96C49—H500.98
C84—H860.96C55—H560.96
C84—H870.96C55—H570.96
C95—C981.510 (5)C55—H580.96
C95—H960.97C51—H520.96
C95—H970.97C51—H530.96
C61—C631.376 (5)C51—H540.96
O111—Si1—O112100.63 (9)H71—C70—H72109.5
O111—Si1—O110106.54 (10)C68—C70—H73109.5
O112—Si1—O110106.23 (10)H71—C70—H73109.5
O111—Si1—S114117.33 (8)H72—C70—H73109.5
O112—Si1—S114114.03 (8)C102—C105—H106109.5
O110—Si1—S114111.02 (7)C102—C105—H107109.5
C59—O112—Si1130.91 (16)H106—C105—H107109.5
C1—O110—Si1129.81 (17)C102—C105—H108109.5
C30—O111—Si1139.54 (17)H106—C105—H108109.5
C102—N109—C95114.7 (2)H107—C105—H108109.5
C102—N109—C88111.9 (2)C7—C9—C1118.2 (2)
C95—N109—C88110.5 (2)C7—C9—C20120.6 (2)
C102—N109—H115109.8 (18)C1—C9—C20121.1 (2)
C95—N109—H115103.9 (19)C88—C91—H92109.5
C88—N109—H115105.4 (19)C88—C91—H93109.5
C36—C38—C30116.9 (3)H92—C91—H93109.5
C36—C38—C49119.3 (3)C88—C91—H94109.5
C30—C38—C49123.8 (2)H92—C91—H94109.5
C167—C78—C80112.7 (3)H93—C91—H94109.5
C167—C78—C84110.1 (3)C10—C16—H17109.5
C80—C78—C84110.1 (3)C10—C16—H18109.5
C167—C78—H79107.9H17—C16—H18109.5
C80—C78—H79107.9C10—C16—H19109.5
C84—C78—H79107.9H17—C16—H19109.5
O110—C1—C2120.5 (2)H18—C16—H19109.5
O110—C1—C9118.0 (2)C61—C60—C59117.8 (3)
C2—C1—C9121.4 (2)C61—C60—C68119.6 (3)
C3—C5—C7119.9 (3)C59—C60—C68122.5 (2)
C3—C5—H6120C34—C36—C38122.6 (3)
C7—C5—H6120C34—C36—H37118.7
C32—C31—C30118.4 (3)C38—C36—H37118.7
C32—C31—C39120.8 (3)C91—C88—N109113.1 (3)
C30—C31—C39120.8 (2)C91—C88—H89108.9
C1—C2—C3118.1 (2)N109—C88—H89108.9
C1—C2—C10123.1 (2)C91—C88—H90108.9
C3—C2—C10118.8 (2)N109—C88—H90108.9
C41—C39—C31113.3 (3)H89—C88—H90107.8
C41—C39—C45110.3 (3)C10—C12—H13109.5
C31—C39—C45109.8 (2)C10—C12—H14109.5
C41—C39—H40107.7H13—C12—H14109.5
C31—C39—H40107.7C10—C12—H15109.5
C45—C39—H40107.7H13—C12—H15109.5
C39—C45—H46109.5H14—C12—H15109.5
C39—C45—H47109.5C63—C65—C167121.6 (3)
H46—C45—H47109.5C63—C65—H66119.2
C39—C45—H48109.5C167—C65—H66119.2
H46—C45—H48109.5C78—C80—H81109.5
H47—C45—H48109.5C78—C80—H82109.5
C2—C10—C16112.0 (3)H81—C80—H82109.5
C2—C10—C12110.5 (2)C78—C80—H83109.5
C16—C10—C12110.5 (2)H81—C80—H83109.5
C2—C10—H11107.9H82—C80—H83109.5
C16—C10—H11107.9C95—C98—H99109.5
C12—C10—H11107.9C95—C98—H100109.5
C39—C41—H42109.5H99—C98—H100109.5
C39—C41—H43109.5C95—C98—H101109.5
H42—C41—H43109.5H99—C98—H101109.5
C39—C41—H44109.5H100—C98—H101109.5
H42—C41—H44109.5C65—C167—C59117.7 (3)
H43—C41—H44109.5C65—C167—C78119.3 (3)
C20—C22—H23109.5C59—C167—C78122.9 (2)
C20—C22—H24109.5O112—C59—C60118.7 (2)
H23—C22—H24109.5O112—C59—C167119.6 (2)
C20—C22—H25109.5C60—C59—C167121.6 (2)
H23—C22—H25109.5C20—C26—H27109.5
H24—C22—H25109.5C20—C26—H28109.5
C36—C34—C32119.1 (3)H27—C26—H28109.5
C36—C34—H35120.4C20—C26—H29109.5
C32—C34—H35120.4H27—C26—H29109.5
C9—C20—C22110.3 (3)H28—C26—H29109.5
C9—C20—C26113.9 (3)C5—C7—C9121.2 (3)
C22—C20—C26110.1 (3)C5—C7—H8119.4
C9—C20—H21107.4C9—C7—H8119.4
C22—C20—H21107.4C68—C74—H75109.5
C26—C20—H21107.4C68—C74—H76109.5
C5—C3—C2121.3 (3)H75—C74—H76109.5
C5—C3—H4119.4C68—C74—H77109.5
C2—C3—H4119.4H75—C74—H77109.5
C78—C84—H85109.5H76—C74—H77109.5
C78—C84—H86109.5C61—C63—C65119.6 (3)
H85—C84—H86109.5C61—C63—H64120.2
C78—C84—H87109.5C65—C63—H64120.2
H85—C84—H87109.5N109—C102—C105112.4 (3)
H86—C84—H87109.5N109—C102—H103109.1
N109—C95—C98113.8 (3)C105—C102—H103109.1
N109—C95—H96108.8N109—C102—H104109.1
C98—C95—H96108.8C105—C102—H104109.1
N109—C95—H97108.8H103—C102—H104107.9
C98—C95—H97108.8C38—C49—C55112.7 (3)
H96—C95—H97107.7C38—C49—C51111.1 (3)
O111—C30—C31118.1 (2)C55—C49—C51109.0 (3)
O111—C30—C38119.9 (2)C38—C49—H50108
C31—C30—C38121.8 (2)C55—C49—H50108
C63—C61—C60121.6 (3)C51—C49—H50108
C63—C61—H62119.2C49—C55—H56109.5
C60—C61—H62119.2C49—C55—H57109.5
C31—C32—C34121.2 (3)H56—C55—H57109.5
C31—C32—H33119.4C49—C55—H58109.5
C34—C32—H33119.4H56—C55—H58109.5
C60—C68—C74110.1 (3)H57—C55—H58109.5
C60—C68—C70112.4 (3)C49—C51—H52109.5
C74—C68—C70109.9 (3)C49—C51—H53109.5
C60—C68—H69108.1H52—C51—H53109.5
C74—C68—H69108.1C49—C51—H54109.5
C70—C68—H69108.1H52—C51—H54109.5
C68—C70—H71109.5H53—C51—H54109.5
C68—C70—H72109.5
O111—Si1—O112—C5916.9 (3)C2—C1—C9—C20177.4 (3)
O110—Si1—O112—C5994.0 (2)C22—C20—C9—C786.8 (3)
S114—Si1—O112—C59143.4 (2)C26—C20—C9—C737.7 (4)
O111—Si1—O110—C1134.2 (2)C22—C20—C9—C190.7 (3)
O112—Si1—O110—C1119.1 (2)C26—C20—C9—C1144.8 (3)
S114—Si1—O110—C15.4 (2)C63—C61—C60—C590.2 (5)
O112—Si1—O111—C30165.6 (3)C63—C61—C60—C68177.5 (3)
O110—Si1—O111—C3055.0 (3)C74—C68—C60—C6165.1 (4)
S114—Si1—O111—C3070.1 (3)C70—C68—C60—C6157.8 (4)
Si1—O110—C1—C278.1 (3)C74—C68—C60—C59112.5 (3)
Si1—O110—C1—C9105.4 (3)C70—C68—C60—C59124.6 (3)
O110—C1—C2—C3176.5 (2)C32—C34—C36—C380.9 (5)
C9—C1—C2—C30.2 (4)C30—C38—C36—C340.1 (5)
O110—C1—C2—C100.8 (4)C49—C38—C36—C34179.1 (3)
C9—C1—C2—C10177.1 (3)C102—N109—C88—C9169.4 (4)
C32—C31—C39—C4130.8 (4)C95—N109—C88—C91161.5 (3)
C30—C31—C39—C41152.6 (3)C63—C65—C167—C590.9 (5)
C32—C31—C39—C4593.0 (3)C63—C65—C167—C78176.1 (3)
C30—C31—C39—C4583.6 (3)C80—C78—C167—C6554.6 (4)
C1—C2—C10—C16129.5 (3)C84—C78—C167—C6568.7 (3)
C3—C2—C10—C1653.2 (4)C80—C78—C167—C59128.5 (3)
C1—C2—C10—C12106.9 (3)C84—C78—C167—C59108.1 (3)
C3—C2—C10—C1270.4 (3)Si1—O112—C59—C60103.8 (3)
C7—C5—C3—C20.1 (5)Si1—O112—C59—C16780.9 (3)
C1—C2—C3—C50.3 (4)C61—C60—C59—O112177.2 (3)
C10—C2—C3—C5177.1 (3)C68—C60—C59—O1120.5 (4)
C102—N109—C95—C9859.2 (4)C61—C60—C59—C1672.0 (4)
C88—N109—C95—C9868.5 (4)C68—C60—C59—C167175.7 (3)
Si1—O111—C30—C3195.3 (3)C65—C167—C59—O112177.5 (3)
Si1—O111—C30—C3890.4 (3)C78—C167—C59—O1120.6 (4)
C32—C31—C30—O111176.2 (2)C65—C167—C59—C602.3 (4)
C39—C31—C30—O1110.5 (4)C78—C167—C59—C60174.6 (3)
C32—C31—C30—C381.9 (4)C3—C5—C7—C90.3 (5)
C39—C31—C30—C38174.8 (2)C1—C9—C7—C50.5 (4)
C36—C38—C30—O111175.5 (2)C20—C9—C7—C5177.1 (3)
C49—C38—C30—O1113.5 (4)C60—C61—C63—C651.1 (6)
C36—C38—C30—C311.3 (4)C167—C65—C63—C610.8 (5)
C49—C38—C30—C31177.6 (3)C95—N109—C102—C10559.8 (4)
C30—C31—C32—C341.1 (4)C88—N109—C102—C105173.2 (3)
C39—C31—C32—C34175.6 (3)C36—C38—C49—C5568.5 (3)
C36—C34—C32—C310.3 (5)C30—C38—C49—C55112.6 (3)
O110—C1—C9—C7176.2 (2)C36—C38—C49—C5154.1 (4)
C2—C1—C9—C70.2 (4)C30—C38—C49—C51124.8 (3)
O110—C1—C9—C206.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N109—H115···S1140.90 (3)2.20 (3)3.086 (3)169 (3)
(tdst_et3n_210) top
Crystal data top
C36H51O3SSi·C6H16NF(000) = 1520
Mr = 694.11Dx = 1.099 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2159 reflections
a = 11.7471 (14) Åθ = 3.1–29.0°
b = 17.9659 (15) ŵ = 0.14 mm1
c = 20.250 (2) ÅT = 210 K
β = 100.904 (9)°Block, colourless
V = 4196.6 (7) Å30.34 × 0.22 × 0.13 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
6652 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.070
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.2°
rotation method scansh = 1414
20955 measured reflectionsk = 1922
8106 independent reflectionsl = 2424
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0546P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max < 0.001
S = 0.97Δρmax = 0.38 e Å3
8106 reflectionsΔρmin = 0.20 e Å3
452 parametersAbsolute structure: Flack x determined using 2735 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 0.05 (6)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.55640 (7)0.26217 (4)0.06094 (4)0.02175 (19)
S1140.40929 (7)0.20963 (5)0.01672 (5)0.0320 (2)
O1120.54748 (19)0.35395 (11)0.05777 (12)0.0273 (5)
O1100.59177 (19)0.23995 (12)0.14198 (12)0.0265 (5)
O1110.6731 (2)0.24827 (12)0.02840 (12)0.0275 (5)
N1090.1980 (3)0.28290 (18)0.07379 (16)0.0355 (7)
H1150.266 (3)0.2645 (19)0.0517 (19)0.021 (9)*
C380.7314 (3)0.14417 (19)0.03227 (18)0.0316 (8)
C780.5836 (3)0.3857 (2)0.07800 (19)0.0354 (8)
H790.53960.34430.06370.042*
C10.5328 (3)0.19694 (18)0.18166 (16)0.0257 (7)
C50.4258 (4)0.1120 (2)0.2667 (2)0.0412 (9)
H60.39010.08360.29540.049*
C310.8559 (3)0.1912 (2)0.07046 (19)0.0322 (8)
C20.4392 (3)0.2268 (2)0.20633 (17)0.0297 (7)
C390.8800 (3)0.2489 (2)0.1265 (2)0.0363 (9)
H400.80590.26180.1390.044*
C450.9294 (4)0.3196 (2)0.1006 (2)0.0492 (10)
H461.00360.30890.08960.074*
H470.9380.35720.13490.074*
H480.87750.3370.06130.074*
C100.3954 (3)0.3055 (2)0.19118 (19)0.0353 (8)
H110.43340.32560.15590.042*
C410.9613 (4)0.2208 (3)0.1899 (2)0.0531 (11)
H420.93050.17580.20510.08*
H430.96790.25790.22450.08*
H441.03650.2110.17970.08*
C220.6226 (5)0.0472 (3)0.1063 (3)0.0628 (13)
H230.5840.00340.11810.094*
H240.68480.03290.08430.094*
H250.56830.07750.07650.094*
C340.9189 (4)0.0883 (2)0.0093 (2)0.0487 (10)
H350.97450.05260.0050.058*
C200.6710 (3)0.0909 (2)0.1694 (2)0.0376 (8)
H210.71630.13220.15610.045*
C30.3870 (3)0.1822 (2)0.24940 (18)0.0372 (9)
H40.32460.2010.26640.045*
C840.4974 (4)0.4388 (3)0.1194 (3)0.0562 (11)
H850.53790.48160.13150.084*
H860.44130.45420.09330.084*
H870.45880.4140.15940.084*
C950.1074 (4)0.2486 (3)0.0398 (2)0.0454 (10)
H960.11330.19490.04240.054*
H970.12370.26240.00730.054*
C300.7518 (3)0.19289 (18)0.02300 (17)0.0272 (7)
C610.7604 (4)0.5043 (2)0.0962 (2)0.0478 (10)
H620.79760.53180.13290.057*
C320.9378 (3)0.1381 (2)0.0629 (2)0.0427 (9)
H331.00670.13570.09420.051*
C680.6571 (4)0.4354 (2)0.1759 (2)0.0400 (9)
H690.60480.39260.17360.048*
C700.7655 (5)0.4185 (3)0.2277 (2)0.0585 (12)
H710.80330.37550.21390.088*
H720.74440.40910.27050.088*
H730.81710.46040.23150.088*
C1050.2260 (6)0.3972 (3)0.0040 (3)0.0676 (15)
H1060.2370.450.00620.101*
H1070.29510.37470.02090.101*
H1080.16210.3870.01790.101*
C90.5736 (3)0.12466 (19)0.19869 (17)0.0296 (7)
C910.2945 (5)0.2623 (3)0.1728 (3)0.0638 (14)
H920.28560.23710.21530.096*
H930.35990.2420.14250.096*
H940.30670.31440.17910.096*
C160.2646 (3)0.3082 (3)0.1654 (2)0.0509 (11)
H170.24340.27180.13060.076*
H180.2430.35690.14770.076*
H190.2250.29770.20170.076*
C600.6833 (3)0.44843 (19)0.1060 (2)0.0350 (8)
C360.8184 (4)0.0922 (2)0.0370 (2)0.0425 (9)
H370.80720.05920.0730.051*
C880.1886 (4)0.2519 (3)0.1443 (2)0.0526 (11)
H890.17150.19910.14350.063*
H900.12410.27580.17360.063*
C120.4283 (4)0.3555 (2)0.2536 (2)0.0456 (10)
H130.39110.33740.28880.068*
H140.40340.40560.24230.068*
H150.51080.35470.26860.068*
C650.7270 (4)0.4802 (2)0.0216 (2)0.0456 (10)
H660.74230.49130.06390.055*
C800.6645 (4)0.3537 (3)0.1213 (3)0.0606 (13)
H810.61960.32880.15950.091*
H820.71650.31880.09540.091*
H830.70830.39320.13640.091*
C980.0145 (4)0.2713 (3)0.0696 (3)0.0629 (13)
H990.02890.26290.11720.094*
H1000.02480.32320.06090.094*
H1010.06790.24240.04960.094*
C1670.6481 (3)0.4240 (2)0.01525 (18)0.0329 (8)
C590.6288 (3)0.40799 (17)0.04961 (19)0.0275 (7)
C260.7535 (4)0.0430 (3)0.2183 (3)0.0655 (14)
H270.71470.00180.22750.098*
H280.77850.070.25940.098*
H290.81960.03050.1990.098*
C70.5184 (4)0.0830 (2)0.24166 (19)0.0384 (9)
H80.54410.03510.25360.046*
C740.5956 (5)0.5028 (3)0.1975 (3)0.0628 (13)
H750.57940.49450.24160.094*
H760.52430.51070.16630.094*
H770.64430.54580.19820.094*
C630.7830 (4)0.5199 (2)0.0333 (2)0.0534 (11)
H640.83580.55690.02790.064*
C1020.2008 (4)0.3656 (2)0.0741 (2)0.0497 (10)
H1030.12670.38430.09760.06*
H1040.25990.38220.09840.06*
C490.6223 (3)0.1461 (2)0.08646 (19)0.0380 (9)
H500.57640.18940.07810.046*
C550.5474 (4)0.0768 (3)0.0860 (2)0.0530 (11)
H560.590.03380.09550.08*
H570.47830.08170.11970.08*
H580.52680.07140.04260.08*
C510.6526 (5)0.1549 (3)0.1566 (2)0.0569 (12)
H520.70080.1980.15710.085*
H530.58260.16090.18940.085*
H540.69310.11150.16720.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0202 (4)0.0228 (4)0.0227 (5)0.0003 (4)0.0052 (4)0.0005 (4)
S1140.0251 (4)0.0284 (4)0.0402 (5)0.0049 (4)0.0002 (4)0.0006 (4)
O1120.0240 (11)0.0277 (11)0.0312 (13)0.0026 (10)0.0073 (10)0.0021 (10)
O1100.0234 (11)0.0319 (12)0.0253 (12)0.0025 (9)0.0075 (10)0.0032 (9)
O1110.0266 (11)0.0304 (12)0.0279 (13)0.0018 (9)0.0109 (10)0.0003 (9)
N1090.0297 (16)0.0443 (19)0.0307 (18)0.0009 (14)0.0011 (14)0.0062 (13)
C380.0341 (19)0.0315 (18)0.031 (2)0.0029 (15)0.0097 (16)0.0011 (14)
C780.039 (2)0.038 (2)0.029 (2)0.0072 (16)0.0071 (17)0.0035 (15)
C10.0242 (15)0.0326 (18)0.0194 (17)0.0044 (13)0.0016 (13)0.0010 (13)
C50.050 (2)0.045 (2)0.032 (2)0.0129 (18)0.0169 (19)0.0013 (16)
C310.0287 (17)0.0369 (19)0.033 (2)0.0001 (14)0.0101 (16)0.0023 (15)
C20.0274 (17)0.038 (2)0.0230 (18)0.0030 (14)0.0031 (15)0.0011 (14)
C390.0275 (18)0.046 (2)0.036 (2)0.0029 (15)0.0089 (16)0.0068 (16)
C450.041 (2)0.048 (2)0.061 (3)0.0089 (19)0.015 (2)0.012 (2)
C100.0313 (18)0.043 (2)0.034 (2)0.0079 (15)0.0130 (16)0.0057 (16)
C410.043 (2)0.078 (3)0.035 (2)0.008 (2)0.001 (2)0.006 (2)
C220.070 (3)0.068 (3)0.053 (3)0.018 (3)0.018 (3)0.014 (2)
C340.047 (2)0.045 (2)0.054 (3)0.017 (2)0.009 (2)0.003 (2)
C200.038 (2)0.0292 (18)0.047 (2)0.0044 (15)0.0128 (18)0.0046 (16)
C30.0356 (19)0.049 (2)0.030 (2)0.0066 (16)0.0142 (17)0.0006 (16)
C840.052 (3)0.057 (3)0.056 (3)0.004 (2)0.000 (2)0.001 (2)
C950.039 (2)0.059 (3)0.039 (2)0.0049 (18)0.0086 (19)0.0117 (19)
C300.0262 (16)0.0285 (17)0.0293 (19)0.0031 (13)0.0115 (15)0.0013 (13)
C610.053 (2)0.040 (2)0.048 (3)0.0205 (19)0.002 (2)0.0080 (18)
C320.0312 (19)0.051 (2)0.044 (3)0.0093 (17)0.0014 (18)0.0047 (18)
C680.051 (2)0.035 (2)0.033 (2)0.0109 (17)0.0071 (19)0.0073 (16)
C700.073 (3)0.059 (3)0.041 (3)0.001 (2)0.005 (2)0.006 (2)
C1050.105 (4)0.048 (3)0.050 (3)0.018 (3)0.017 (3)0.004 (2)
C90.0318 (18)0.0304 (17)0.0253 (19)0.0025 (14)0.0021 (15)0.0009 (14)
C910.074 (3)0.073 (3)0.051 (3)0.005 (3)0.028 (3)0.015 (2)
C160.034 (2)0.072 (3)0.046 (3)0.010 (2)0.006 (2)0.006 (2)
C600.0373 (19)0.0312 (18)0.035 (2)0.0059 (15)0.0037 (16)0.0019 (15)
C360.046 (2)0.034 (2)0.048 (2)0.0086 (17)0.012 (2)0.0086 (17)
C880.053 (3)0.066 (3)0.037 (2)0.006 (2)0.003 (2)0.006 (2)
C120.049 (2)0.042 (2)0.046 (2)0.0113 (19)0.009 (2)0.0011 (18)
C650.052 (2)0.043 (2)0.044 (3)0.0145 (19)0.013 (2)0.0076 (18)
C800.061 (3)0.073 (3)0.051 (3)0.002 (2)0.017 (3)0.018 (2)
C980.040 (2)0.107 (4)0.042 (3)0.005 (3)0.007 (2)0.016 (3)
C1670.0348 (19)0.0297 (18)0.035 (2)0.0026 (14)0.0083 (17)0.0027 (14)
C590.0247 (16)0.0221 (16)0.036 (2)0.0016 (13)0.0073 (15)0.0032 (14)
C260.056 (3)0.072 (3)0.066 (3)0.024 (2)0.003 (3)0.004 (3)
C70.049 (2)0.0294 (19)0.036 (2)0.0046 (16)0.0073 (18)0.0054 (15)
C740.080 (4)0.062 (3)0.050 (3)0.017 (3)0.022 (3)0.002 (2)
C630.060 (3)0.043 (2)0.059 (3)0.027 (2)0.015 (2)0.003 (2)
C1020.060 (3)0.046 (2)0.044 (3)0.005 (2)0.013 (2)0.0041 (19)
C490.041 (2)0.043 (2)0.030 (2)0.0085 (17)0.0073 (17)0.0047 (16)
C550.054 (3)0.055 (3)0.046 (3)0.007 (2)0.000 (2)0.009 (2)
C510.071 (3)0.068 (3)0.033 (2)0.016 (2)0.013 (2)0.000 (2)
Geometric parameters (Å, º) top
Si1—O1111.648 (2)C61—C601.392 (5)
Si1—O1121.653 (2)C61—H620.93
Si1—O1101.664 (2)C32—H330.93
Si1—S1142.0233 (12)C68—C741.515 (6)
O112—C591.394 (4)C68—C701.520 (6)
O110—C11.391 (4)C68—C601.523 (5)
O111—C301.377 (4)C68—H690.98
N109—C1021.486 (5)C70—H710.96
N109—C951.503 (5)C70—H720.96
N109—C881.518 (5)C70—H730.96
N109—H1150.90 (4)C105—C1021.505 (7)
C38—C361.401 (5)C105—H1060.96
C38—C301.405 (5)C105—H1070.96
C38—C491.521 (6)C105—H1080.96
C78—C1671.516 (5)C9—C71.397 (5)
C78—C841.522 (6)C91—C881.479 (7)
C78—C801.523 (6)C91—H920.96
C78—H790.98C91—H930.96
C1—C21.397 (5)C91—H940.96
C1—C91.404 (5)C16—H170.96
C5—C31.364 (6)C16—H180.96
C5—C71.385 (6)C16—H190.96
C5—H60.93C60—C591.402 (5)
C31—C321.383 (5)C36—H370.93
C31—C301.405 (5)C88—H890.97
C31—C391.523 (5)C88—H900.97
C2—C31.408 (5)C12—H130.96
C2—C101.517 (5)C12—H140.96
C39—C451.529 (6)C12—H150.96
C39—C411.533 (6)C65—C631.378 (6)
C39—H400.98C65—C1671.394 (5)
C45—H460.96C65—H660.93
C45—H470.96C80—H810.96
C45—H480.96C80—H820.96
C10—C161.528 (5)C80—H830.96
C10—C121.539 (6)C98—H990.96
C10—H110.98C98—H1000.96
C41—H420.96C98—H1010.96
C41—H430.96C167—C591.404 (5)
C41—H440.96C26—H270.96
C22—C201.518 (6)C26—H280.96
C22—H230.96C26—H290.96
C22—H240.96C7—H80.93
C22—H250.96C74—H750.96
C34—C361.363 (6)C74—H760.96
C34—C321.393 (6)C74—H770.96
C34—H350.93C63—H640.93
C20—C91.511 (5)C102—H1030.97
C20—C261.515 (6)C102—H1040.97
C20—H210.98C49—C551.525 (6)
C3—H40.93C49—C511.537 (6)
C84—H850.96C49—H500.98
C84—H860.96C55—H560.96
C84—H870.96C55—H570.96
C95—C981.502 (6)C55—H580.96
C95—H960.97C51—H520.96
C95—H970.97C51—H530.96
C61—C631.378 (6)C51—H540.96
O111—Si1—O112100.78 (12)H71—C70—H72109.5
O111—Si1—O110106.66 (12)C68—C70—H73109.5
O112—Si1—O110106.25 (12)H71—C70—H73109.5
O111—Si1—S114117.23 (10)H72—C70—H73109.5
O112—Si1—S114113.94 (10)C102—C105—H106109.5
O110—Si1—S114110.96 (9)C102—C105—H107109.5
C59—O112—Si1131.3 (2)H106—C105—H107109.5
C1—O110—Si1130.1 (2)C102—C105—H108109.5
C30—O111—Si1139.7 (2)H106—C105—H108109.5
C102—N109—C95115.5 (3)H107—C105—H108109.5
C102—N109—C88111.2 (3)C7—C9—C1118.1 (3)
C95—N109—C88110.4 (3)C7—C9—C20120.3 (3)
C102—N109—H115110 (2)C1—C9—C20121.5 (3)
C95—N109—H115105 (2)C88—C91—H92109.5
C88—N109—H115103 (2)C88—C91—H93109.5
C36—C38—C30116.9 (3)H92—C91—H93109.5
C36—C38—C49119.5 (3)C88—C91—H94109.5
C30—C38—C49123.6 (3)H92—C91—H94109.5
C167—C78—C84110.6 (3)H93—C91—H94109.5
C167—C78—C80112.8 (3)C10—C16—H17109.5
C84—C78—C80110.0 (4)C10—C16—H18109.5
C167—C78—H79107.7H17—C16—H18109.5
C84—C78—H79107.7C10—C16—H19109.5
C80—C78—H79107.7H17—C16—H19109.5
O110—C1—C2120.3 (3)H18—C16—H19109.5
O110—C1—C9118.1 (3)C61—C60—C59117.8 (4)
C2—C1—C9121.5 (3)C61—C60—C68119.7 (3)
C3—C5—C7120.0 (3)C59—C60—C68122.4 (3)
C3—C5—H6120C34—C36—C38122.4 (4)
C7—C5—H6120C34—C36—H37118.8
C32—C31—C30118.2 (3)C38—C36—H37118.8
C32—C31—C39121.0 (3)C91—C88—N109113.8 (4)
C30—C31—C39120.7 (3)C91—C88—H89108.8
C1—C2—C3117.9 (3)N109—C88—H89108.8
C1—C2—C10123.1 (3)C91—C88—H90108.8
C3—C2—C10119.0 (3)N109—C88—H90108.8
C31—C39—C45109.9 (3)H89—C88—H90107.7
C31—C39—C41113.5 (3)C10—C12—H13109.5
C45—C39—C41110.1 (3)C10—C12—H14109.5
C31—C39—H40107.7H13—C12—H14109.5
C45—C39—H40107.7C10—C12—H15109.5
C41—C39—H40107.7H13—C12—H15109.5
C39—C45—H46109.5H14—C12—H15109.5
C39—C45—H47109.5C63—C65—C167121.6 (4)
H46—C45—H47109.5C63—C65—H66119.2
C39—C45—H48109.5C167—C65—H66119.2
H46—C45—H48109.5C78—C80—H81109.5
H47—C45—H48109.5C78—C80—H82109.5
C2—C10—C16112.3 (3)H81—C80—H82109.5
C2—C10—C12110.8 (3)C78—C80—H83109.5
C16—C10—C12110.0 (3)H81—C80—H83109.5
C2—C10—H11107.9H82—C80—H83109.5
C16—C10—H11107.9C95—C98—H99109.5
C12—C10—H11107.9C95—C98—H100109.5
C39—C41—H42109.5H99—C98—H100109.5
C39—C41—H43109.5C95—C98—H101109.5
H42—C41—H43109.5H99—C98—H101109.5
C39—C41—H44109.5H100—C98—H101109.5
H42—C41—H44109.5C65—C167—C59117.6 (3)
H43—C41—H44109.5C65—C167—C78119.2 (3)
C20—C22—H23109.5C59—C167—C78123.2 (3)
C20—C22—H24109.5O112—C59—C60118.8 (3)
H23—C22—H24109.5O112—C59—C167119.3 (3)
C20—C22—H25109.5C60—C59—C167121.8 (3)
H23—C22—H25109.5C20—C26—H27109.5
H24—C22—H25109.5C20—C26—H28109.5
C36—C34—C32119.5 (4)H27—C26—H28109.5
C36—C34—H35120.3C20—C26—H29109.5
C32—C34—H35120.3H27—C26—H29109.5
C9—C20—C26114.2 (3)H28—C26—H29109.5
C9—C20—C22110.3 (3)C5—C7—C9121.1 (3)
C26—C20—C22110.3 (4)C5—C7—H8119.4
C9—C20—H21107.2C9—C7—H8119.4
C26—C20—H21107.2C68—C74—H75109.5
C22—C20—H21107.2C68—C74—H76109.5
C5—C3—C2121.5 (3)H75—C74—H76109.5
C5—C3—H4119.3C68—C74—H77109.5
C2—C3—H4119.3H75—C74—H77109.5
C78—C84—H85109.5H76—C74—H77109.5
C78—C84—H86109.5C65—C63—C61119.7 (4)
H85—C84—H86109.5C65—C63—H64120.2
C78—C84—H87109.5C61—C63—H64120.2
H85—C84—H87109.5N109—C102—C105111.9 (4)
H86—C84—H87109.5N109—C102—H103109.2
C98—C95—N109114.2 (3)C105—C102—H103109.2
C98—C95—H96108.7N109—C102—H104109.2
N109—C95—H96108.7C105—C102—H104109.2
C98—C95—H97108.7H103—C102—H104107.9
N109—C95—H97108.7C38—C49—C55112.6 (3)
H96—C95—H97107.6C38—C49—C51111.0 (3)
O111—C30—C38119.8 (3)C55—C49—C51108.9 (4)
O111—C30—C31118.2 (3)C38—C49—H50108
C38—C30—C31121.8 (3)C55—C49—H50108
C63—C61—C60121.5 (4)C51—C49—H50108
C63—C61—H62119.2C49—C55—H56109.5
C60—C61—H62119.2C49—C55—H57109.5
C31—C32—C34121.2 (4)H56—C55—H57109.5
C31—C32—H33119.4C49—C55—H58109.5
C34—C32—H33119.4H56—C55—H58109.5
C74—C68—C70110.1 (4)H57—C55—H58109.5
C74—C68—C60109.7 (3)C49—C51—H52109.5
C70—C68—C60112.5 (4)C49—C51—H53109.5
C74—C68—H69108.2H52—C51—H53109.5
C70—C68—H69108.2C49—C51—H54109.5
C60—C68—H69108.2H52—C51—H54109.5
C68—C70—H71109.5H53—C51—H54109.5
C68—C70—H72109.5
O111—Si1—O112—C5917.0 (3)C2—C1—C9—C20177.1 (3)
O110—Si1—O112—C5994.0 (3)C26—C20—C9—C740.0 (5)
S114—Si1—O112—C59143.5 (3)C22—C20—C9—C784.9 (4)
O111—Si1—O110—C1133.6 (3)C26—C20—C9—C1142.6 (4)
O112—Si1—O110—C1119.5 (3)C22—C20—C9—C192.5 (4)
S114—Si1—O110—C14.8 (3)C63—C61—C60—C590.0 (6)
O112—Si1—O111—C30165.2 (3)C63—C61—C60—C68177.4 (4)
O110—Si1—O111—C3054.4 (4)C74—C68—C60—C6165.2 (5)
S114—Si1—O111—C3070.6 (4)C70—C68—C60—C6157.6 (5)
Si1—O110—C1—C278.5 (4)C74—C68—C60—C59112.1 (4)
Si1—O110—C1—C9104.6 (3)C70—C68—C60—C59125.1 (4)
O110—C1—C2—C3176.4 (3)C32—C34—C36—C381.0 (6)
C9—C1—C2—C30.3 (5)C30—C38—C36—C340.1 (6)
O110—C1—C2—C100.9 (5)C49—C38—C36—C34179.0 (4)
C9—C1—C2—C10177.7 (3)C102—N109—C88—C9169.7 (5)
C32—C31—C39—C4593.1 (4)C95—N109—C88—C91160.8 (4)
C30—C31—C39—C4583.7 (4)C63—C65—C167—C591.1 (6)
C32—C31—C39—C4130.7 (5)C63—C65—C167—C78176.2 (4)
C30—C31—C39—C41152.5 (3)C84—C78—C167—C6569.1 (5)
C1—C2—C10—C16129.3 (4)C80—C78—C167—C6554.6 (5)
C3—C2—C10—C1653.3 (5)C84—C78—C167—C59108.0 (4)
C1—C2—C10—C12107.2 (4)C80—C78—C167—C59128.3 (4)
C3—C2—C10—C1270.1 (4)Si1—O112—C59—C60103.3 (3)
C7—C5—C3—C20.2 (6)Si1—O112—C59—C16781.0 (4)
C1—C2—C3—C50.0 (5)C61—C60—C59—O112177.3 (3)
C10—C2—C3—C5177.5 (4)C68—C60—C59—O1120.1 (5)
C102—N109—C95—C9858.6 (5)C61—C60—C59—C1671.7 (5)
C88—N109—C95—C9868.5 (5)C68—C60—C59—C167175.7 (4)
Si1—O111—C30—C3890.4 (4)C65—C167—C59—O112177.8 (3)
Si1—O111—C30—C3195.2 (4)C78—C167—C59—O1120.6 (5)
C36—C38—C30—O111175.9 (3)C65—C167—C59—C602.2 (5)
C49—C38—C30—O1113.1 (5)C78—C167—C59—C60175.0 (3)
C36—C38—C30—C311.7 (5)C3—C5—C7—C90.2 (6)
C49—C38—C30—C31177.3 (3)C1—C9—C7—C50.1 (5)
C32—C31—C30—O111176.5 (3)C20—C9—C7—C5177.3 (4)
C39—C31—C30—O1110.4 (5)C167—C65—C63—C610.5 (7)
C32—C31—C30—C382.1 (5)C60—C61—C63—C651.0 (7)
C39—C31—C30—C38174.8 (3)C95—N109—C102—C10560.9 (5)
C30—C31—C32—C341.0 (6)C88—N109—C102—C105172.4 (4)
C39—C31—C32—C34175.9 (4)C36—C38—C49—C5567.8 (4)
C36—C34—C32—C310.6 (6)C30—C38—C49—C55113.2 (4)
O110—C1—C9—C7176.4 (3)C36—C38—C49—C5154.6 (5)
C2—C1—C9—C70.4 (5)C30—C38—C49—C51124.4 (4)
O110—C1—C9—C206.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N109—H115···S1140.90 (4)2.20 (4)3.087 (3)168 (3)
(tdst_et3n_temp_240) top
Crystal data top
C36H51O3SSi·C6H16NF(000) = 1520
Mr = 694.11Dx = 1.093 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 807 reflections
a = 11.801 (2) Åθ = 3.1–27.8°
b = 18.019 (2) ŵ = 0.14 mm1
c = 20.201 (4) ÅT = 240 K
β = 100.958 (15)°Block, colourless
V = 4217.1 (13) Å30.34 × 0.22 × 0.13 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
4927 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.045
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.2°
rotation method scansh = 1214
7448 measured reflectionsk = 1722
5960 independent reflectionsl = 2423
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.059 w = 1/[σ2(Fo2) + (0.1347P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.181(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.36 e Å3
5960 reflectionsΔρmin = 0.45 e Å3
452 parametersAbsolute structure: Classical Flack method preferred over Parsons because s.u. lower.
2 restraintsAbsolute structure parameter: 0.20 (15)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.55619 (9)0.26273 (7)0.06093 (7)0.0267 (3)
S1140.41002 (11)0.21026 (7)0.01677 (8)0.0381 (3)
O1120.5485 (3)0.35391 (18)0.05773 (19)0.0311 (7)
O1100.5916 (3)0.2407 (2)0.14212 (18)0.0325 (8)
O1110.6726 (3)0.2482 (2)0.02845 (19)0.0332 (8)
N1090.1968 (4)0.2829 (3)0.0733 (3)0.0436 (12)
H1150.255 (5)0.266 (3)0.052 (3)0.019 (13)*
C380.7315 (5)0.1438 (3)0.0315 (3)0.0376 (12)
C780.5832 (5)0.3858 (3)0.0782 (3)0.0421 (13)
H790.53920.34470.06380.05*
C10.5330 (4)0.1973 (3)0.1813 (3)0.0306 (10)
C50.4270 (6)0.1127 (4)0.2666 (3)0.0501 (15)
H60.39240.08450.29580.06*
C310.8557 (5)0.1921 (3)0.0707 (3)0.0383 (12)
C20.4395 (5)0.2276 (3)0.2064 (3)0.0341 (11)
C390.8792 (5)0.2503 (4)0.1259 (3)0.0434 (13)
H400.80530.26320.13830.052*
C450.9285 (6)0.3211 (4)0.0999 (4)0.0598 (18)
H460.99830.30930.08430.09*
H470.94470.35680.13570.09*
H480.87310.34140.06340.09*
C100.3956 (5)0.3054 (3)0.1910 (3)0.0400 (12)
H110.43340.32540.15560.048*
C410.9601 (7)0.2226 (5)0.1896 (4)0.067 (2)
H420.93130.17660.20390.101*
H430.96380.25880.22480.101*
H441.03590.21490.18010.101*
C220.6227 (8)0.0464 (6)0.1071 (4)0.078 (2)
H230.59190.00060.12040.117*
H240.68370.03580.08310.117*
H250.56280.07360.07840.117*
C340.9180 (6)0.0893 (4)0.0100 (4)0.0608 (18)
H350.97330.05360.0060.073*
C200.6695 (5)0.0917 (3)0.1686 (3)0.0460 (13)
H210.71330.13280.15410.055*
C30.3877 (5)0.1825 (4)0.2492 (3)0.0453 (14)
H40.32510.20080.2660.054*
C840.4976 (7)0.4390 (5)0.1187 (4)0.067 (2)
H850.53750.48240.12950.101*
H860.44090.4530.09270.101*
H870.46020.41520.15960.101*
C950.1076 (6)0.2481 (5)0.0403 (4)0.0555 (17)
H960.12280.26180.0070.067*
H970.11480.19460.04270.067*
C300.7511 (4)0.1939 (3)0.0230 (3)0.0345 (11)
C610.7582 (7)0.5051 (4)0.0959 (4)0.0595 (18)
H620.79470.53250.13290.071*
C320.9362 (6)0.1399 (4)0.0632 (4)0.0546 (16)
H331.0050.1380.09450.065*
C680.6572 (6)0.4363 (4)0.1756 (3)0.0494 (15)
H690.60550.39340.17330.059*
C700.7646 (8)0.4195 (5)0.2268 (4)0.073 (2)
H710.79780.37380.21520.109*
H720.74520.4150.27070.109*
H730.81940.4590.22720.109*
C1050.2292 (10)0.3970 (5)0.0040 (5)0.085 (3)
H1060.23240.45010.00670.128*
H1070.30250.37840.01880.128*
H1080.17040.38290.02050.128*
C90.5735 (5)0.1252 (3)0.1981 (3)0.0355 (11)
C910.2944 (8)0.2614 (6)0.1717 (5)0.076 (2)
H920.28440.23820.21520.113*
H930.3590.23930.14210.113*
H940.30840.31350.17620.113*
C160.2662 (6)0.3072 (5)0.1649 (4)0.0607 (19)
H170.24570.26980.13090.091*
H180.24440.35510.14580.091*
H190.22670.29790.20140.091*
C600.6823 (5)0.4492 (3)0.1055 (3)0.0436 (13)
C360.8176 (6)0.0932 (4)0.0360 (4)0.0520 (15)
H370.80640.06030.07210.062*
C880.1893 (7)0.2510 (6)0.1434 (4)0.069 (2)
H890.17310.19830.1420.083*
H900.12490.2740.17340.083*
C120.4284 (6)0.3555 (4)0.2537 (4)0.0551 (16)
H130.38960.33830.28850.083*
H140.40570.40570.2420.083*
H150.51040.35350.26960.083*
C650.7243 (6)0.4807 (4)0.0220 (4)0.0576 (17)
H660.73850.49190.06460.069*
C800.6636 (7)0.3535 (6)0.1210 (4)0.073 (2)
H810.61970.32510.15720.11*
H820.71930.3220.09370.11*
H830.70280.39310.13930.11*
C980.0147 (7)0.2696 (6)0.0708 (5)0.078 (3)
H990.02590.26590.1190.117*
H1000.02880.31960.05830.117*
H1010.06740.23670.05450.117*
C1670.6474 (5)0.4240 (3)0.0153 (3)0.0404 (12)
C590.6278 (5)0.4078 (3)0.0490 (3)0.0353 (11)
C260.7544 (7)0.0450 (6)0.2183 (5)0.078 (2)
H270.71670.00070.22920.117*
H280.78080.07320.25860.117*
H290.81920.03190.19820.117*
C70.5185 (6)0.0836 (3)0.2408 (3)0.0446 (13)
H80.54350.03550.25220.054*
C740.5953 (8)0.5026 (6)0.1972 (4)0.077 (2)
H750.58510.49570.24290.115*
H760.52130.50770.16820.115*
H770.64030.54650.19450.115*
C630.7808 (7)0.5212 (5)0.0336 (4)0.070 (2)
H640.83290.55840.02830.083*
C1020.2014 (7)0.3650 (4)0.0739 (4)0.0621 (18)
H1030.12750.38420.09680.075*
H1040.25950.38080.0990.075*
C490.6228 (5)0.1459 (4)0.0859 (3)0.0446 (13)
H500.57710.18910.07730.054*
C550.5491 (7)0.0773 (5)0.0850 (4)0.066 (2)
H560.59230.03430.09320.099*
H570.48110.08130.11950.099*
H580.52710.07290.04180.099*
C510.6538 (8)0.1554 (5)0.1559 (4)0.069 (2)
H520.70790.19530.15470.104*
H530.58520.16640.18830.104*
H540.68750.11030.16850.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0205 (6)0.0342 (6)0.0260 (7)0.0011 (5)0.0060 (5)0.0003 (6)
S1140.0277 (6)0.0421 (6)0.0418 (7)0.0069 (5)0.0004 (5)0.0001 (6)
O1120.0255 (16)0.0320 (16)0.0373 (18)0.0057 (14)0.0099 (13)0.0006 (16)
O1100.0236 (16)0.047 (2)0.0277 (18)0.0050 (14)0.0067 (13)0.0013 (15)
O1110.0264 (17)0.044 (2)0.0308 (19)0.0002 (14)0.0104 (14)0.0009 (15)
N1090.029 (2)0.059 (3)0.039 (3)0.002 (2)0.001 (2)0.010 (2)
C380.033 (3)0.044 (3)0.037 (3)0.002 (2)0.009 (2)0.000 (2)
C780.044 (3)0.049 (3)0.033 (3)0.007 (2)0.009 (2)0.003 (2)
C10.024 (2)0.041 (3)0.026 (2)0.0017 (18)0.0034 (19)0.004 (2)
C50.060 (4)0.060 (4)0.035 (3)0.015 (3)0.020 (3)0.001 (3)
C310.029 (3)0.051 (3)0.034 (3)0.002 (2)0.005 (2)0.001 (2)
C20.031 (3)0.043 (3)0.030 (3)0.006 (2)0.008 (2)0.000 (2)
C390.028 (3)0.065 (4)0.038 (3)0.004 (2)0.007 (2)0.010 (3)
C450.045 (3)0.066 (4)0.069 (5)0.008 (3)0.013 (3)0.013 (4)
C100.035 (3)0.051 (3)0.037 (3)0.013 (2)0.013 (2)0.009 (2)
C410.053 (4)0.104 (6)0.041 (4)0.011 (4)0.000 (3)0.011 (4)
C220.080 (6)0.096 (6)0.057 (5)0.027 (5)0.013 (4)0.020 (4)
C340.049 (4)0.060 (4)0.073 (5)0.026 (3)0.011 (3)0.007 (4)
C200.045 (3)0.045 (3)0.051 (4)0.008 (2)0.016 (3)0.005 (3)
C30.046 (3)0.061 (4)0.033 (3)0.006 (3)0.018 (3)0.001 (3)
C840.054 (4)0.083 (5)0.058 (4)0.002 (4)0.010 (3)0.002 (4)
C950.044 (4)0.077 (5)0.046 (4)0.001 (3)0.007 (3)0.020 (3)
C300.027 (2)0.044 (3)0.034 (3)0.004 (2)0.010 (2)0.003 (2)
C610.067 (4)0.055 (4)0.056 (4)0.026 (3)0.008 (3)0.006 (3)
C320.039 (3)0.063 (4)0.059 (4)0.012 (3)0.004 (3)0.009 (3)
C680.060 (4)0.051 (3)0.037 (3)0.013 (3)0.008 (3)0.008 (3)
C700.086 (6)0.079 (5)0.051 (4)0.009 (4)0.007 (4)0.009 (4)
C1050.130 (8)0.069 (5)0.057 (5)0.024 (5)0.015 (5)0.005 (4)
C90.038 (3)0.039 (3)0.029 (3)0.001 (2)0.005 (2)0.001 (2)
C910.080 (6)0.094 (7)0.055 (5)0.003 (4)0.019 (4)0.015 (4)
C160.039 (3)0.086 (5)0.055 (4)0.017 (3)0.005 (3)0.006 (4)
C600.043 (3)0.047 (3)0.041 (3)0.005 (2)0.008 (2)0.003 (3)
C360.054 (4)0.054 (4)0.049 (4)0.012 (3)0.013 (3)0.012 (3)
C880.064 (5)0.095 (6)0.048 (4)0.009 (4)0.008 (4)0.011 (4)
C120.060 (4)0.055 (4)0.052 (4)0.013 (3)0.015 (3)0.003 (3)
C650.064 (4)0.060 (4)0.052 (4)0.024 (3)0.019 (3)0.009 (3)
C800.071 (5)0.097 (6)0.054 (4)0.003 (4)0.017 (4)0.022 (4)
C980.044 (4)0.134 (8)0.054 (5)0.003 (4)0.007 (3)0.023 (5)
C1670.040 (3)0.048 (3)0.033 (3)0.006 (2)0.007 (2)0.004 (2)
C590.030 (2)0.038 (3)0.039 (3)0.002 (2)0.007 (2)0.004 (2)
C260.061 (5)0.094 (6)0.075 (6)0.029 (4)0.001 (4)0.002 (5)
C70.055 (3)0.042 (3)0.039 (3)0.004 (2)0.013 (3)0.003 (2)
C740.082 (6)0.092 (6)0.059 (5)0.018 (5)0.021 (4)0.006 (4)
C630.069 (5)0.066 (4)0.073 (5)0.043 (4)0.012 (4)0.010 (4)
C1020.077 (5)0.053 (4)0.058 (4)0.002 (3)0.014 (4)0.003 (3)
C490.043 (3)0.056 (4)0.034 (3)0.010 (3)0.005 (2)0.004 (3)
C550.063 (5)0.076 (5)0.054 (4)0.015 (4)0.001 (3)0.013 (4)
C510.088 (6)0.087 (6)0.033 (3)0.014 (4)0.011 (3)0.000 (3)
Geometric parameters (Å, º) top
Si1—O1121.646 (3)C61—C601.386 (9)
Si1—O1111.652 (4)C61—H620.93
Si1—O1101.662 (4)C32—H330.93
Si1—S1142.0199 (18)C68—C741.508 (11)
O112—C591.382 (6)C68—C701.508 (11)
O110—C11.387 (6)C68—C601.518 (9)
O111—C301.367 (7)C68—H690.98
N109—C1021.481 (9)C70—H710.96
N109—C951.487 (8)C70—H720.96
N109—C881.516 (10)C70—H730.96
N109—H1150.80 (6)C105—C1021.502 (12)
C38—C361.381 (9)C105—H1060.96
C38—C301.408 (8)C105—H1070.96
C38—C491.523 (8)C105—H1080.96
C78—C841.514 (10)C9—C71.393 (8)
C78—C1671.515 (8)C91—C881.473 (12)
C78—C801.517 (10)C91—H920.96
C78—H790.98C91—H930.96
C1—C91.403 (7)C91—H940.96
C1—C21.408 (7)C16—H170.96
C5—C31.364 (10)C16—H180.96
C5—C71.388 (9)C16—H190.96
C5—H60.93C60—C591.412 (8)
C31—C321.365 (9)C36—H370.93
C31—C301.415 (8)C88—H890.97
C31—C391.518 (8)C88—H900.97
C2—C31.407 (8)C12—H130.96
C2—C101.507 (8)C12—H140.96
C39—C411.534 (10)C12—H150.96
C39—C451.535 (10)C65—C1671.389 (9)
C39—H400.98C65—C631.399 (11)
C45—H460.96C65—H660.93
C45—H470.96C80—H810.96
C45—H480.96C80—H820.96
C10—C161.518 (9)C80—H830.96
C10—C121.544 (10)C98—H990.96
C10—H110.98C98—H1000.96
C41—H420.96C98—H1010.96
C41—H430.96C167—C591.394 (8)
C41—H440.96C26—H270.96
C22—C201.502 (11)C26—H280.96
C22—H230.96C26—H290.96
C22—H240.96C7—H80.93
C22—H250.96C74—H750.96
C34—C361.361 (10)C74—H760.96
C34—C321.396 (11)C74—H770.96
C34—H350.93C63—H640.93
C20—C91.504 (8)C102—H1030.97
C20—C261.528 (10)C102—H1040.97
C20—H210.98C49—C551.513 (10)
C3—H40.93C49—C511.536 (10)
C84—H850.96C49—H500.98
C84—H860.96C55—H560.96
C84—H870.96C55—H570.96
C95—C981.509 (10)C55—H580.96
C95—H960.97C51—H520.96
C95—H970.97C51—H530.96
C61—C631.367 (11)C51—H540.96
O112—Si1—O111100.74 (19)H71—C70—H72109.5
O112—Si1—O110106.2 (2)C68—C70—H73109.5
O111—Si1—O110106.39 (18)H71—C70—H73109.5
O112—Si1—S114114.44 (14)H72—C70—H73109.5
O111—Si1—S114117.08 (15)C102—C105—H106109.5
O110—Si1—S114110.96 (14)C102—C105—H107109.5
C59—O112—Si1132.2 (3)H106—C105—H107109.5
C1—O110—Si1129.7 (3)C102—C105—H108109.5
C30—O111—Si1140.6 (4)H106—C105—H108109.5
C102—N109—C95117.1 (6)H107—C105—H108109.5
C102—N109—C88111.5 (6)C7—C9—C1118.1 (5)
C95—N109—C88109.8 (6)C7—C9—C20120.2 (5)
C102—N109—H115111 (4)C1—C9—C20121.6 (5)
C95—N109—H115102 (4)C88—C91—H92109.5
C88—N109—H115105 (4)C88—C91—H93109.5
C36—C38—C30117.5 (5)H92—C91—H93109.5
C36—C38—C49119.9 (5)C88—C91—H94109.5
C30—C38—C49122.6 (5)H92—C91—H94109.5
C84—C78—C167110.0 (5)H93—C91—H94109.5
C84—C78—C80111.1 (6)C10—C16—H17109.5
C167—C78—C80112.6 (5)C10—C16—H18109.5
C84—C78—H79107.6H17—C16—H18109.5
C167—C78—H79107.6C10—C16—H19109.5
C80—C78—H79107.6H17—C16—H19109.5
O110—C1—C9118.5 (4)H18—C16—H19109.5
O110—C1—C2119.7 (4)C61—C60—C59118.6 (6)
C9—C1—C2121.7 (5)C61—C60—C68119.2 (6)
C3—C5—C7120.2 (5)C59—C60—C68122.1 (5)
C3—C5—H6119.9C34—C36—C38123.0 (6)
C7—C5—H6119.9C34—C36—H37118.5
C32—C31—C30118.4 (6)C38—C36—H37118.5
C32—C31—C39121.6 (6)C91—C88—N109114.2 (6)
C30—C31—C39119.9 (5)C91—C88—H89108.7
C3—C2—C1117.3 (5)N109—C88—H89108.7
C3—C2—C10119.4 (5)C91—C88—H90108.7
C1—C2—C10123.3 (5)N109—C88—H90108.7
C31—C39—C41112.9 (6)H89—C88—H90107.6
C31—C39—C45110.5 (5)C10—C12—H13109.5
C41—C39—C45110.0 (6)C10—C12—H14109.5
C31—C39—H40107.7H13—C12—H14109.5
C41—C39—H40107.7C10—C12—H15109.5
C45—C39—H40107.7H13—C12—H15109.5
C39—C45—H46109.5H14—C12—H15109.5
C39—C45—H47109.5C167—C65—C63121.7 (6)
H46—C45—H47109.5C167—C65—H66119.2
C39—C45—H48109.5C63—C65—H66119.2
H46—C45—H48109.5C78—C80—H81109.5
H47—C45—H48109.5C78—C80—H82109.5
C2—C10—C16112.0 (6)H81—C80—H82109.5
C2—C10—C12110.6 (5)C78—C80—H83109.5
C16—C10—C12110.6 (5)H81—C80—H83109.5
C2—C10—H11107.8H82—C80—H83109.5
C16—C10—H11107.8C95—C98—H99109.5
C12—C10—H11107.8C95—C98—H100109.5
C39—C41—H42109.5H99—C98—H100109.5
C39—C41—H43109.5C95—C98—H101109.5
H42—C41—H43109.5H99—C98—H101109.5
C39—C41—H44109.5H100—C98—H101109.5
H42—C41—H44109.5C65—C167—C59118.2 (6)
H43—C41—H44109.5C65—C167—C78118.9 (5)
C20—C22—H23109.5C59—C167—C78122.8 (5)
C20—C22—H24109.5O112—C59—C167120.1 (5)
H23—C22—H24109.5O112—C59—C60119.0 (5)
C20—C22—H25109.5C167—C59—C60120.8 (5)
H23—C22—H25109.5C20—C26—H27109.5
H24—C22—H25109.5C20—C26—H28109.5
C36—C34—C32118.6 (6)H27—C26—H28109.5
C36—C34—H35120.7C20—C26—H29109.5
C32—C34—H35120.7H27—C26—H29109.5
C22—C20—C9111.1 (6)H28—C26—H29109.5
C22—C20—C26109.7 (6)C5—C7—C9121.0 (5)
C9—C20—C26114.3 (6)C5—C7—H8119.5
C22—C20—H21107.1C9—C7—H8119.5
C9—C20—H21107.1C68—C74—H75109.5
C26—C20—H21107.1C68—C74—H76109.5
C5—C3—C2121.6 (6)H75—C74—H76109.5
C5—C3—H4119.2C68—C74—H77109.5
C2—C3—H4119.2H75—C74—H77109.5
C78—C84—H85109.5H76—C74—H77109.5
C78—C84—H86109.5C61—C63—C65118.9 (6)
H85—C84—H86109.5C61—C63—H64120.6
C78—C84—H87109.5C65—C63—H64120.6
H85—C84—H87109.5N109—C102—C105112.1 (6)
H86—C84—H87109.5N109—C102—H103109.2
N109—C95—C98114.4 (6)C105—C102—H103109.2
N109—C95—H96108.7N109—C102—H104109.2
C98—C95—H96108.7C105—C102—H104109.2
N109—C95—H97108.7H103—C102—H104107.9
C98—C95—H97108.7C55—C49—C38112.2 (6)
H96—C95—H97107.6C55—C49—C51109.8 (6)
O111—C30—C38120.6 (5)C38—C49—C51110.6 (6)
O111—C30—C31118.6 (5)C55—C49—H50108
C38—C30—C31120.6 (5)C38—C49—H50108
C63—C61—C60121.8 (7)C51—C49—H50108
C63—C61—H62119.1C49—C55—H56109.5
C60—C61—H62119.1C49—C55—H57109.5
C31—C32—C34121.8 (6)H56—C55—H57109.5
C31—C32—H33119.1C49—C55—H58109.5
C34—C32—H33119.1H56—C55—H58109.5
C74—C68—C70110.5 (6)H57—C55—H58109.5
C74—C68—C60109.9 (6)C49—C51—H52109.5
C70—C68—C60112.5 (6)C49—C51—H53109.5
C74—C68—H69107.9H52—C51—H53109.5
C70—C68—H69107.9C49—C51—H54109.5
C60—C68—H69107.9H52—C51—H54109.5
C68—C70—H71109.5H53—C51—H54109.5
C68—C70—H72109.5
O111—Si1—O112—C5916.2 (5)C2—C1—C9—C20177.0 (5)
O110—Si1—O112—C5994.5 (5)C22—C20—C9—C782.7 (7)
S114—Si1—O112—C59142.7 (4)C26—C20—C9—C742.1 (8)
O112—Si1—O110—C1120.7 (4)C22—C20—C9—C194.3 (7)
O111—Si1—O110—C1132.5 (4)C26—C20—C9—C1140.9 (6)
S114—Si1—O110—C14.2 (5)C63—C61—C60—C590.3 (12)
O112—Si1—O111—C30164.7 (6)C63—C61—C60—C68177.5 (8)
O110—Si1—O111—C3054.1 (6)C74—C68—C60—C6165.5 (9)
S114—Si1—O111—C3070.6 (6)C70—C68—C60—C6158.1 (9)
Si1—O110—C1—C9104.1 (5)C74—C68—C60—C59112.2 (7)
Si1—O110—C1—C279.5 (6)C70—C68—C60—C59124.2 (7)
O110—C1—C2—C3176.2 (5)C32—C34—C36—C381.6 (12)
C9—C1—C2—C30.0 (8)C30—C38—C36—C341.0 (11)
O110—C1—C2—C102.1 (8)C49—C38—C36—C34178.5 (7)
C9—C1—C2—C10178.3 (5)C102—N109—C88—C9168.1 (9)
C32—C31—C39—C4131.2 (9)C95—N109—C88—C91160.4 (7)
C30—C31—C39—C41152.5 (6)C63—C65—C167—C590.3 (11)
C32—C31—C39—C4592.5 (8)C63—C65—C167—C78175.9 (7)
C30—C31—C39—C4583.8 (7)C84—C78—C167—C6568.4 (8)
C3—C2—C10—C1653.1 (7)C80—C78—C167—C6556.0 (9)
C1—C2—C10—C16128.6 (6)C84—C78—C167—C59107.7 (7)
C3—C2—C10—C1270.7 (7)C80—C78—C167—C59127.9 (7)
C1—C2—C10—C12107.6 (6)Si1—O112—C59—C16780.2 (7)
C7—C5—C3—C21.6 (10)Si1—O112—C59—C60104.0 (6)
C1—C2—C3—C50.9 (8)C65—C167—C59—O112177.4 (6)
C10—C2—C3—C5177.6 (6)C78—C167—C59—O1121.3 (9)
C102—N109—C95—C9859.3 (9)C65—C167—C59—C601.7 (9)
C88—N109—C95—C9869.1 (9)C78—C167—C59—C60174.5 (5)
Si1—O111—C30—C3889.3 (7)C61—C60—C59—O112177.4 (6)
Si1—O111—C30—C3194.9 (7)C68—C60—C59—O1120.3 (9)
C36—C38—C30—O111176.2 (6)C61—C60—C59—C1671.7 (9)
C49—C38—C30—O1111.2 (9)C68—C60—C59—C167176.1 (6)
C36—C38—C30—C310.4 (9)C3—C5—C7—C91.4 (10)
C49—C38—C30—C31177.0 (5)C1—C9—C7—C50.6 (8)
C32—C31—C30—O111177.0 (6)C20—C9—C7—C5177.7 (6)
C39—C31—C30—O1110.6 (8)C60—C61—C63—C651.0 (14)
C32—C31—C30—C381.2 (9)C167—C65—C63—C611.0 (13)
C39—C31—C30—C38175.2 (5)C95—N109—C102—C10562.2 (9)
C30—C31—C32—C340.5 (11)C88—N109—C102—C105170.2 (7)
C39—C31—C32—C34175.8 (6)C36—C38—C49—C5568.4 (8)
C36—C34—C32—C310.8 (12)C30—C38—C49—C55114.2 (7)
O110—C1—C9—C7176.2 (5)C36—C38—C49—C5154.6 (9)
C2—C1—C9—C70.1 (8)C30—C38—C49—C51122.8 (6)
O110—C1—C9—C206.8 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N109—H115···S1140.80 (6)2.31 (7)3.101 (5)174 (5)
(tdst_py_temp_90) top
Crystal data top
C36H51O3SSi·C5H6NF(000) = 1456
Mr = 672.02Dx = 1.134 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7852 reflections
a = 13.4301 (11) Åθ = 3–28.5°
b = 16.2937 (8) ŵ = 0.15 mm1
c = 18.8001 (14) ÅT = 90 K
β = 106.835 (6)°Plate, colorless
V = 3937.6 (5) Å30.38 × 0.31 × 0.15 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
5724 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.039
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.1°
rotation method scansh = 1316
21931 measured reflectionsk = 1920
7717 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.055P)2 + 1.3584P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7717 reflectionsΔρmax = 0.64 e Å3
440 parametersΔρmin = 0.51 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S920.59663 (4)0.52562 (3)0.08971 (2)0.01925 (12)
Si910.68561 (4)0.51389 (3)0.19666 (3)0.01487 (12)
O900.62829 (10)0.45436 (8)0.24460 (7)0.0169 (3)
O880.70800 (10)0.59826 (8)0.24731 (7)0.0179 (3)
O890.80042 (10)0.47124 (8)0.20478 (7)0.0168 (3)
C600.92939 (14)0.48577 (12)0.14139 (10)0.0188 (4)
N1030.40549 (14)0.43770 (12)0.10495 (9)0.0251 (4)
C650.84821 (15)0.35020 (13)0.05265 (10)0.0206 (4)
H650.82190.30490.02310.025*
C590.84216 (14)0.44379 (12)0.14980 (9)0.0156 (4)
C670.80149 (14)0.37435 (12)0.10706 (10)0.0171 (4)
C90.57180 (15)0.50596 (13)0.34642 (11)0.0227 (4)
C310.86545 (16)0.66447 (13)0.31481 (11)0.0241 (4)
C950.30929 (18)0.33332 (14)0.13960 (13)0.0322 (5)
H950.30660.28710.16810.039*
C630.93240 (16)0.39190 (14)0.04176 (10)0.0238 (4)
H630.96140.37550.00470.029*
C20.70613 (15)0.39916 (13)0.36697 (10)0.0205 (4)
C1010.32028 (18)0.47031 (15)0.05901 (12)0.0316 (5)
H1010.3250.51730.03210.038*
C10.63700 (14)0.45433 (12)0.32033 (10)0.0181 (4)
C800.76468 (17)0.23924 (13)0.15610 (11)0.0243 (4)
H80A0.79210.20980.12170.037*
H80B0.71220.20670.16820.037*
H80C0.81970.25050.20060.037*
C780.71662 (14)0.32046 (12)0.12066 (10)0.0184 (4)
H780.68760.34870.15620.022*
C680.97703 (16)0.55789 (13)0.18999 (12)0.0235 (4)
H680.9420.56260.22890.028*
C100.77082 (16)0.33850 (13)0.33762 (11)0.0240 (4)
H100.75870.34980.28460.029*
C610.97288 (15)0.45837 (13)0.08669 (11)0.0217 (4)
H611.03060.48550.08020.026*
C70.57957 (18)0.50193 (15)0.42215 (12)0.0315 (5)
H70.5370.53540.44090.038*
C30.71076 (17)0.39873 (15)0.44233 (11)0.0276 (5)
H30.75670.36330.47450.033*
C320.93165 (16)0.73163 (14)0.32309 (12)0.0285 (5)
H320.99260.73250.36230.034*
C930.40237 (17)0.37079 (15)0.14476 (12)0.0300 (5)
H930.46360.34940.17620.036*
C380.74883 (16)0.73069 (13)0.20427 (11)0.0230 (4)
C300.77479 (15)0.66443 (12)0.25379 (10)0.0197 (4)
C290.38266 (16)0.53717 (15)0.28616 (13)0.0308 (5)
H29A0.37290.48190.26780.046*
H29B0.33580.5730.25160.046*
H29C0.36890.53990.33340.046*
C490.64837 (17)0.73373 (14)0.14014 (12)0.0283 (5)
H490.61410.68040.13870.034*
C200.49448 (16)0.56366 (14)0.29507 (12)0.0261 (5)
H200.50610.5610.2460.031*
C390.88707 (17)0.59522 (14)0.37117 (12)0.0298 (5)
H390.85540.54530.34520.036*
C990.22541 (18)0.43448 (18)0.05136 (12)0.0381 (6)
H990.16540.45690.01930.046*
C360.81811 (18)0.79664 (14)0.21618 (13)0.0296 (5)
H360.80270.84140.18410.036*
C160.7363 (2)0.25072 (15)0.34485 (13)0.0336 (5)
H16A0.74650.23810.39630.05*
H16B0.77680.21370.32470.05*
H16C0.6640.24490.31810.05*
C970.21980 (17)0.36500 (16)0.09166 (12)0.0331 (5)
H970.15610.33970.08660.04*
C50.64865 (19)0.44976 (16)0.46993 (12)0.0334 (5)
H50.65330.4490.52020.04*
C840.62745 (16)0.30375 (14)0.05008 (11)0.0245 (4)
H84A0.59690.35490.02930.037*
H84B0.57570.27050.06220.037*
H84C0.65390.27550.01460.037*
C220.51228 (19)0.65215 (16)0.32222 (16)0.0422 (6)
H22A0.50320.65620.37090.063*
H22B0.46320.68730.28860.063*
H22C0.58170.66860.32420.063*
C340.90890 (18)0.79728 (14)0.27421 (13)0.0329 (5)
H340.95450.84150.28040.039*
C510.6675 (2)0.7454 (3)0.06600 (15)0.0678 (10)
H51A0.69640.7990.06390.102*
H51B0.6030.74040.02730.102*
H51C0.71540.70440.05940.102*
C700.9590 (3)0.63752 (16)0.14621 (16)0.0512 (8)
H70A0.99670.63630.110.077*
H70B0.98270.68280.17950.077*
H70C0.8860.64380.12150.077*
C120.88668 (19)0.34763 (18)0.3753 (2)0.0566 (9)
H12A0.9080.40260.36840.085*
H12B0.92430.30950.35390.085*
H12C0.9010.33660.42750.085*
C410.83510 (19)0.61267 (18)0.43164 (14)0.0417 (6)
H41A0.86580.66060.4590.063*
H41B0.84460.56660.46470.063*
H41C0.76210.62190.40930.063*
C550.5739 (2)0.7983 (2)0.15327 (18)0.0664 (10)
H55A0.55520.7850.19750.1*
H55B0.51250.79970.11160.1*
H55C0.60710.85110.15910.1*
C451.00251 (19)0.57803 (18)0.40586 (14)0.0418 (6)
H45A1.03520.56980.36730.063*
H45B1.01080.52960.43610.063*
H45C1.03430.62380.43610.063*
C741.09251 (19)0.54464 (19)0.22824 (19)0.0580 (9)
H74A1.10170.49570.25780.087*
H74B1.11970.59080.25960.087*
H74C1.12880.53910.19140.087*
H1030.469 (3)0.461 (2)0.1066 (17)0.062 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S920.0183 (2)0.0209 (3)0.0177 (2)0.00266 (19)0.00388 (17)0.00065 (18)
Si910.0122 (2)0.0165 (3)0.0164 (2)0.0012 (2)0.00498 (18)0.00077 (19)
O900.0151 (6)0.0199 (7)0.0167 (6)0.0007 (5)0.0064 (5)0.0001 (5)
O880.0138 (6)0.0188 (7)0.0208 (6)0.0017 (5)0.0047 (5)0.0039 (5)
O890.0139 (6)0.0205 (7)0.0173 (6)0.0002 (5)0.0064 (5)0.0023 (5)
C600.0155 (9)0.0197 (10)0.0216 (9)0.0018 (8)0.0064 (7)0.0046 (8)
N1030.0241 (9)0.0279 (10)0.0265 (9)0.0025 (8)0.0126 (7)0.0005 (7)
C650.0224 (10)0.0226 (11)0.0172 (9)0.0015 (8)0.0064 (7)0.0011 (7)
C590.0143 (9)0.0174 (9)0.0159 (8)0.0027 (7)0.0057 (7)0.0024 (7)
C670.0158 (9)0.0187 (10)0.0171 (8)0.0015 (7)0.0051 (7)0.0026 (7)
C90.0175 (9)0.0257 (11)0.0279 (10)0.0005 (8)0.0112 (8)0.0005 (8)
C310.0182 (10)0.0220 (11)0.0309 (10)0.0022 (8)0.0053 (8)0.0078 (8)
C950.0294 (12)0.0262 (12)0.0427 (13)0.0013 (9)0.0132 (10)0.0107 (10)
C630.0226 (10)0.0329 (12)0.0198 (9)0.0041 (9)0.0121 (8)0.0036 (8)
C20.0175 (9)0.0247 (11)0.0207 (9)0.0003 (8)0.0075 (7)0.0017 (8)
C1010.0365 (12)0.0364 (13)0.0288 (11)0.0098 (10)0.0204 (10)0.0126 (9)
C10.0140 (9)0.0240 (11)0.0172 (8)0.0038 (8)0.0056 (7)0.0006 (7)
C800.0271 (11)0.0196 (11)0.0285 (10)0.0010 (8)0.0114 (8)0.0017 (8)
C780.0170 (9)0.0193 (10)0.0193 (9)0.0009 (8)0.0060 (7)0.0003 (7)
C680.0196 (10)0.0202 (11)0.0339 (10)0.0027 (8)0.0128 (8)0.0008 (9)
C100.0239 (10)0.0252 (11)0.0239 (10)0.0060 (8)0.0084 (8)0.0052 (8)
C610.0169 (9)0.0272 (11)0.0243 (9)0.0004 (8)0.0112 (8)0.0070 (8)
C70.0311 (12)0.0394 (14)0.0305 (11)0.0026 (10)0.0191 (9)0.0051 (10)
C30.0253 (11)0.0351 (13)0.0217 (10)0.0015 (9)0.0059 (8)0.0056 (9)
C320.0169 (10)0.0278 (12)0.0382 (12)0.0011 (8)0.0037 (9)0.0117 (9)
C930.0217 (11)0.0326 (13)0.0337 (11)0.0021 (9)0.0049 (9)0.0087 (9)
C380.0230 (10)0.0187 (11)0.0282 (10)0.0017 (8)0.0087 (8)0.0043 (8)
C300.0163 (9)0.0196 (10)0.0248 (9)0.0014 (8)0.0084 (8)0.0066 (8)
C290.0214 (11)0.0290 (12)0.0425 (12)0.0002 (9)0.0102 (9)0.0021 (10)
C490.0301 (12)0.0220 (11)0.0282 (10)0.0008 (9)0.0013 (9)0.0003 (9)
C200.0193 (10)0.0282 (12)0.0342 (11)0.0054 (9)0.0129 (9)0.0016 (9)
C390.0243 (11)0.0280 (12)0.0300 (11)0.0001 (9)0.0035 (9)0.0033 (9)
C990.0230 (11)0.0642 (18)0.0297 (11)0.0148 (11)0.0115 (9)0.0180 (11)
C360.0343 (12)0.0189 (11)0.0376 (12)0.0028 (9)0.0136 (10)0.0016 (9)
C160.0408 (13)0.0297 (13)0.0324 (11)0.0006 (10)0.0141 (10)0.0011 (10)
C970.0191 (10)0.0477 (15)0.0347 (11)0.0034 (10)0.0110 (9)0.0017 (10)
C50.0371 (13)0.0457 (15)0.0199 (10)0.0008 (11)0.0123 (9)0.0004 (9)
C840.0219 (10)0.0263 (11)0.0259 (10)0.0045 (8)0.0078 (8)0.0019 (8)
C220.0255 (12)0.0286 (13)0.0684 (17)0.0017 (10)0.0072 (11)0.0023 (12)
C340.0276 (11)0.0257 (12)0.0491 (13)0.0096 (9)0.0168 (10)0.0127 (10)
C510.0452 (17)0.118 (3)0.0364 (14)0.0001 (19)0.0059 (12)0.0150 (17)
C700.097 (2)0.0221 (13)0.0524 (15)0.0009 (14)0.0501 (16)0.0010 (11)
C120.0229 (13)0.0400 (16)0.106 (2)0.0053 (11)0.0165 (14)0.0235 (16)
C410.0299 (13)0.0535 (17)0.0394 (13)0.0019 (12)0.0062 (10)0.0107 (12)
C550.0334 (15)0.093 (3)0.0588 (18)0.0227 (16)0.0086 (13)0.0243 (18)
C450.0309 (13)0.0511 (17)0.0369 (13)0.0141 (11)0.0007 (10)0.0017 (11)
C740.0194 (12)0.0539 (19)0.093 (2)0.0052 (12)0.0034 (13)0.0424 (17)
Geometric parameters (Å, º) top
S92—Si912.0286 (7)C93—H930.93
Si91—O881.6496 (14)C38—C361.396 (3)
Si91—O891.6576 (13)C38—C301.402 (3)
Si91—O901.6576 (13)C38—C491.528 (3)
O90—C11.394 (2)C29—C201.525 (3)
O88—C301.385 (2)C29—H29A0.96
O89—C591.385 (2)C29—H29B0.96
C60—C611.395 (3)C29—H29C0.96
C60—C591.405 (3)C49—C511.501 (4)
C60—C681.512 (3)C49—C551.520 (4)
N103—C1011.329 (3)C49—H490.98
N103—C931.330 (3)C20—C221.525 (3)
N103—H1030.93 (3)C20—H200.98
C65—C631.384 (3)C39—C411.523 (3)
C65—C671.402 (3)C39—C451.524 (3)
C65—H650.93C39—H390.98
C59—C671.404 (3)C99—C971.376 (3)
C67—C781.518 (3)C99—H990.93
C9—C71.399 (3)C36—C341.381 (3)
C9—C11.401 (3)C36—H360.93
C9—C201.521 (3)C16—H16A0.96
C31—C321.390 (3)C16—H16B0.96
C31—C301.410 (3)C16—H16C0.96
C31—C391.517 (3)C97—H970.93
C95—C931.369 (3)C5—H50.93
C95—C971.377 (3)C84—H84A0.96
C95—H950.93C84—H84B0.96
C63—C611.384 (3)C84—H84C0.96
C63—H630.93C22—H22A0.96
C2—C31.400 (3)C22—H22B0.96
C2—C11.403 (3)C22—H22C0.96
C2—C101.521 (3)C34—H340.93
C101—C991.371 (3)C51—H51A0.96
C101—H1010.93C51—H51B0.96
C80—C781.537 (3)C51—H51C0.96
C80—H80A0.96C70—H70A0.96
C80—H80B0.96C70—H70B0.96
C80—H80C0.96C70—H70C0.96
C78—C841.532 (3)C12—H12A0.96
C78—H780.98C12—H12B0.96
C68—C701.518 (3)C12—H12C0.96
C68—C741.524 (3)C41—H41A0.96
C68—H680.98C41—H41B0.96
C10—C121.519 (3)C41—H41C0.96
C10—C161.521 (3)C55—H55A0.96
C10—H100.98C55—H55B0.96
C61—H610.93C55—H55C0.96
C7—C51.381 (3)C45—H45A0.96
C7—H70.93C45—H45B0.96
C3—C51.381 (3)C45—H45C0.96
C3—H30.93C74—H74A0.96
C32—C341.385 (3)C74—H74B0.96
C32—H320.93C74—H74C0.96
O88—Si91—O89106.67 (7)H29B—C29—H29C109.5
O88—Si91—O90102.09 (7)C51—C49—C55111.1 (2)
O89—Si91—O90105.70 (7)C51—C49—C38112.8 (2)
O88—Si91—S92116.76 (5)C55—C49—C38111.48 (19)
O89—Si91—S92113.33 (5)C51—C49—H49107
O90—Si91—S92111.16 (5)C55—C49—H49107
C1—O90—Si91129.83 (12)C38—C49—H49107
C30—O88—Si91134.80 (12)C9—C20—C29111.37 (18)
C59—O89—Si91129.30 (11)C9—C20—C22111.10 (19)
C61—C60—C59117.91 (18)C29—C20—C22111.00 (18)
C61—C60—C68120.00 (17)C9—C20—H20107.7
C59—C60—C68122.09 (17)C29—C20—H20107.7
C101—N103—C93122.1 (2)C22—C20—H20107.7
C101—N103—H103118 (2)C31—C39—C41110.24 (19)
C93—N103—H103120 (2)C31—C39—C45113.6 (2)
C63—C65—C67121.83 (19)C41—C39—C45110.14 (18)
C63—C65—H65119.1C31—C39—H39107.5
C67—C65—H65119.1C41—C39—H39107.5
O89—C59—C67120.87 (16)C45—C39—H39107.5
O89—C59—C60117.24 (16)C101—C99—C97119.3 (2)
C67—C59—C60121.81 (17)C101—C99—H99120.3
C65—C67—C59117.49 (17)C97—C99—H99120.3
C65—C67—C78118.49 (17)C34—C36—C38121.8 (2)
C59—C67—C78123.82 (16)C34—C36—H36119.1
C7—C9—C1117.27 (19)C38—C36—H36119.1
C7—C9—C20120.73 (19)C10—C16—H16A109.5
C1—C9—C20122.00 (18)C10—C16—H16B109.5
C32—C31—C30117.7 (2)H16A—C16—H16B109.5
C32—C31—C39121.36 (19)C10—C16—H16C109.5
C30—C31—C39120.88 (19)H16A—C16—H16C109.5
C93—C95—C97119.0 (2)H16B—C16—H16C109.5
C93—C95—H95120.5C99—C97—C95119.5 (2)
C97—C95—H95120.5C99—C97—H97120.3
C61—C63—C65119.15 (18)C95—C97—H97120.3
C61—C63—H63120.4C3—C5—C7119.43 (19)
C65—C63—H63120.4C3—C5—H5120.3
C3—C2—C1117.59 (18)C7—C5—H5120.3
C3—C2—C10120.08 (18)C78—C84—H84A109.5
C1—C2—C10122.26 (17)C78—C84—H84B109.5
N103—C101—C99119.8 (2)H84A—C84—H84B109.5
N103—C101—H101120.1C78—C84—H84C109.5
C99—C101—H101120.1H84A—C84—H84C109.5
O90—C1—C9118.75 (17)H84B—C84—H84C109.5
O90—C1—C2118.89 (17)C20—C22—H22A109.5
C9—C1—C2122.24 (17)C20—C22—H22B109.5
C78—C80—H80A109.5H22A—C22—H22B109.5
C78—C80—H80B109.5C20—C22—H22C109.5
H80A—C80—H80B109.5H22A—C22—H22C109.5
C78—C80—H80C109.5H22B—C22—H22C109.5
H80A—C80—H80C109.5C36—C34—C32119.5 (2)
H80B—C80—H80C109.5C36—C34—H34120.2
C67—C78—C84113.18 (16)C32—C34—H34120.2
C67—C78—C80109.24 (16)C49—C51—H51A109.5
C84—C78—C80110.31 (17)C49—C51—H51B109.5
C67—C78—H78108H51A—C51—H51B109.5
C84—C78—H78108C49—C51—H51C109.5
C80—C78—H78108H51A—C51—H51C109.5
C60—C68—C70111.31 (19)H51B—C51—H51C109.5
C60—C68—C74111.69 (18)C68—C70—H70A109.5
C70—C68—C74111.0 (2)C68—C70—H70B109.5
C60—C68—H68107.5H70A—C70—H70B109.5
C70—C68—H68107.5C68—C70—H70C109.5
C74—C68—H68107.5H70A—C70—H70C109.5
C12—C10—C2112.49 (19)H70B—C70—H70C109.5
C12—C10—C16110.3 (2)C10—C12—H12A109.5
C2—C10—C16110.97 (18)C10—C12—H12B109.5
C12—C10—H10107.6H12A—C12—H12B109.5
C2—C10—H10107.6C10—C12—H12C109.5
C16—C10—H10107.6H12A—C12—H12C109.5
C63—C61—C60121.73 (18)H12B—C12—H12C109.5
C63—C61—H61119.1C39—C41—H41A109.5
C60—C61—H61119.1C39—C41—H41B109.5
C5—C7—C9121.9 (2)H41A—C41—H41B109.5
C5—C7—H7119C39—C41—H41C109.5
C9—C7—H7119H41A—C41—H41C109.5
C5—C3—C2121.5 (2)H41B—C41—H41C109.5
C5—C3—H3119.2C49—C55—H55A109.5
C2—C3—H3119.2C49—C55—H55B109.5
C34—C32—C31121.5 (2)H55A—C55—H55B109.5
C34—C32—H32119.2C49—C55—H55C109.5
C31—C32—H32119.2H55A—C55—H55C109.5
N103—C93—C95120.2 (2)H55B—C55—H55C109.5
N103—C93—H93119.9C39—C45—H45A109.5
C95—C93—H93119.9C39—C45—H45B109.5
C36—C38—C30117.39 (19)H45A—C45—H45B109.5
C36—C38—C49119.79 (19)C39—C45—H45C109.5
C30—C38—C49122.81 (19)H45A—C45—H45C109.5
O88—C30—C38120.71 (17)H45B—C45—H45C109.5
O88—C30—C31117.16 (18)C68—C74—H74A109.5
C38—C30—C31121.99 (19)C68—C74—H74B109.5
C20—C29—H29A109.5H74A—C74—H74B109.5
C20—C29—H29B109.5C68—C74—H74C109.5
H29A—C29—H29B109.5H74A—C74—H74C109.5
C20—C29—H29C109.5H74B—C74—H74C109.5
H29A—C29—H29C109.5
O88—Si91—O90—C126.71 (16)C1—C2—C10—C16112.6 (2)
O89—Si91—O90—C184.70 (16)C65—C63—C61—C601.7 (3)
S92—Si91—O90—C1151.93 (14)C59—C60—C61—C630.1 (3)
O89—Si91—O88—C3049.06 (18)C68—C60—C61—C63179.12 (18)
O90—Si91—O88—C30159.74 (17)C1—C9—C7—C50.3 (3)
S92—Si91—O88—C3078.83 (18)C20—C9—C7—C5179.6 (2)
O88—Si91—O89—C59129.62 (15)C1—C2—C3—C50.9 (3)
O90—Si91—O89—C59122.24 (15)C10—C2—C3—C5176.2 (2)
S92—Si91—O89—C590.25 (17)C30—C31—C32—C341.3 (3)
Si91—O89—C59—C6769.1 (2)C39—C31—C32—C34176.0 (2)
Si91—O89—C59—C60113.98 (17)C101—N103—C93—C950.3 (3)
C61—C60—C59—O89179.42 (16)C97—C95—C93—N1031.3 (4)
C68—C60—C59—O890.2 (3)Si91—O88—C30—C3883.4 (2)
C61—C60—C59—C672.5 (3)Si91—O88—C30—C31100.8 (2)
C68—C60—C59—C67176.72 (18)C36—C38—C30—O88177.44 (17)
C63—C65—C67—C591.1 (3)C49—C38—C30—O881.3 (3)
C63—C65—C67—C78173.97 (18)C36—C38—C30—C311.9 (3)
O89—C59—C67—C65179.76 (16)C49—C38—C30—C31176.86 (19)
C60—C59—C67—C653.0 (3)C32—C31—C30—O88178.25 (17)
O89—C59—C67—C785.0 (3)C39—C31—C30—O880.9 (3)
C60—C59—C67—C78171.79 (17)C32—C31—C30—C382.5 (3)
C67—C65—C63—C611.2 (3)C39—C31—C30—C38174.83 (18)
C93—N103—C101—C990.3 (3)C36—C38—C49—C5157.8 (3)
Si91—O90—C1—C987.2 (2)C30—C38—C49—C51123.5 (3)
Si91—O90—C1—C296.7 (2)C36—C38—C49—C5568.0 (3)
C7—C9—C1—O90177.42 (18)C30—C38—C49—C55110.6 (3)
C20—C9—C1—O901.9 (3)C7—C9—C20—C2967.5 (3)
C7—C9—C1—C21.4 (3)C1—C9—C20—C29111.9 (2)
C20—C9—C1—C2177.96 (19)C7—C9—C20—C2256.9 (3)
C3—C2—C1—O90178.01 (17)C1—C9—C20—C22123.8 (2)
C10—C2—C1—O900.9 (3)C32—C31—C39—C4190.4 (2)
C3—C2—C1—C92.0 (3)C30—C31—C39—C4186.8 (2)
C10—C2—C1—C9175.16 (19)C32—C31—C39—C4533.8 (3)
C65—C67—C78—C8454.7 (2)C30—C31—C39—C45149.0 (2)
C59—C67—C78—C84130.57 (19)N103—C101—C99—C970.1 (4)
C65—C67—C78—C8068.6 (2)C30—C38—C36—C340.0 (3)
C59—C67—C78—C80106.1 (2)C49—C38—C36—C34178.8 (2)
C61—C60—C68—C7070.3 (2)C101—C99—C97—C950.8 (4)
C59—C60—C68—C70110.5 (2)C93—C95—C97—C991.5 (4)
C61—C60—C68—C7454.4 (3)C2—C3—C5—C70.6 (4)
C59—C60—C68—C74124.8 (2)C9—C7—C5—C31.3 (4)
C3—C2—C10—C1259.8 (3)C38—C36—C34—C321.2 (3)
C1—C2—C10—C12123.2 (2)C31—C32—C34—C360.5 (3)
C3—C2—C10—C1664.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N103—H103···S920.93 (3)2.11 (3)3.0247 (19)168 (3)
(tdst_py_120) top
Crystal data top
C36H51O3SSi·C5H6NF(000) = 1456
Mr = 672.02Dx = 1.13 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14027 reflections
a = 13.4487 (12) Åθ = 3.4–29.5°
b = 16.3096 (9) ŵ = 0.15 mm1
c = 18.8302 (16) ÅT = 120 K
β = 106.902 (6)°Plate, colorless
V = 3951.9 (5) Å30.38 × 0.31 × 0.15 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
5636 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.043
Detector resolution: 6.67 pixels mm-1θmax = 26°, θmin = 3.1°
rotation method scansh = 1316
21998 measured reflectionsk = 1920
7735 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0545P)2 + 1.4509P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7735 reflectionsΔρmax = 0.47 e Å3
440 parametersΔρmin = 0.50 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S920.59619 (4)0.52584 (3)0.08988 (3)0.02097 (12)
Si910.68571 (4)0.51450 (3)0.19661 (3)0.01572 (12)
O900.62886 (10)0.45533 (8)0.24479 (7)0.0179 (3)
O880.70847 (10)0.59904 (8)0.24690 (7)0.0196 (3)
O890.80028 (10)0.47174 (8)0.20454 (7)0.0180 (3)
C600.92897 (14)0.48603 (12)0.14101 (11)0.0196 (4)
N1030.40553 (15)0.43763 (12)0.10493 (10)0.0292 (4)
C650.84730 (16)0.35089 (13)0.05268 (10)0.0224 (4)
H650.82070.30580.0230.027*
C590.84171 (14)0.44446 (12)0.14966 (10)0.0165 (4)
C670.80110 (15)0.37467 (12)0.10676 (10)0.0185 (4)
C90.57250 (16)0.50676 (14)0.34617 (12)0.0256 (5)
C310.86533 (16)0.66458 (14)0.31475 (12)0.0261 (5)
C950.30962 (18)0.33418 (15)0.14080 (14)0.0373 (6)
H950.30690.28850.16980.045*
C630.93157 (17)0.39217 (14)0.04175 (11)0.0264 (5)
H630.96050.37550.00480.032*
C20.70659 (16)0.40000 (13)0.36705 (11)0.0237 (4)
C1010.3207 (2)0.47000 (16)0.05921 (13)0.0371 (6)
H1010.32530.51680.03210.045*
C10.63759 (15)0.45528 (13)0.32044 (10)0.0197 (4)
C800.76433 (18)0.23999 (13)0.15608 (12)0.0283 (5)
H80A0.79110.21030.12160.042*
H80B0.71210.20770.16860.042*
H80C0.81980.25130.20020.042*
C780.71631 (15)0.32100 (13)0.12069 (11)0.0210 (4)
H780.68770.34940.15620.025*
C680.97654 (16)0.55822 (13)0.18936 (13)0.0268 (5)
H680.94120.56320.22790.032*
C100.77067 (17)0.33940 (14)0.33764 (12)0.0271 (5)
H100.75810.35060.28460.032*
C610.97215 (16)0.45847 (13)0.08650 (11)0.0239 (4)
H611.02990.48540.080.029*
C70.57995 (19)0.50288 (16)0.42178 (13)0.0369 (6)
H70.53740.53630.44040.044*
C30.71083 (18)0.39964 (16)0.44189 (12)0.0332 (5)
H30.75650.36410.47410.04*
C320.93201 (17)0.73172 (15)0.32306 (14)0.0330 (5)
H320.9930.73240.36230.04*
C930.40267 (18)0.37125 (16)0.14537 (13)0.0353 (5)
H930.46390.350.17680.042*
C380.75011 (17)0.73100 (13)0.20394 (12)0.0261 (5)
C300.77527 (15)0.66493 (13)0.25339 (11)0.0212 (4)
C290.38329 (18)0.53786 (16)0.28638 (15)0.0377 (6)
H29A0.37370.48230.26880.057*
H29B0.33650.57320.25140.057*
H29C0.36940.54140.33350.057*
C490.65018 (19)0.73397 (14)0.13965 (12)0.0318 (5)
H490.61680.68020.13730.038*
C200.49506 (17)0.56426 (14)0.29517 (13)0.0303 (5)
H200.50630.56150.24610.036*
C390.88655 (18)0.59586 (15)0.37126 (13)0.0340 (5)
H390.85420.54610.34560.041*
C990.22594 (19)0.4340 (2)0.05199 (14)0.0449 (7)
H990.16590.45590.01960.054*
C360.81986 (19)0.79670 (14)0.21606 (14)0.0346 (5)
H360.80530.84130.18390.041*
C160.7360 (2)0.25162 (16)0.34500 (15)0.0421 (6)
H16A0.74610.23920.39640.063*
H16B0.77640.21450.3250.063*
H16C0.66380.24590.31820.063*
C970.22047 (18)0.36545 (17)0.09280 (14)0.0391 (6)
H970.15680.34030.0880.047*
C50.6493 (2)0.45047 (18)0.46948 (13)0.0403 (6)
H50.65410.44960.51980.048*
C840.62703 (16)0.30447 (14)0.05037 (12)0.0272 (5)
H84A0.59750.35560.02910.041*
H84B0.57470.27220.06270.041*
H84C0.6530.27530.01520.041*
C220.5128 (2)0.65250 (17)0.32183 (18)0.0479 (7)
H22A0.50210.65710.36990.072*
H22B0.46480.68770.28750.072*
H22C0.58260.66840.32490.072*
C340.90967 (19)0.79704 (15)0.27453 (15)0.0381 (6)
H340.95510.84120.28120.046*
C510.6690 (3)0.7481 (3)0.06604 (17)0.0856 (14)
H51A0.69910.80140.06550.128*
H51B0.60430.74490.02740.128*
H51C0.71580.7070.0580.128*
C700.9590 (3)0.63750 (17)0.14556 (18)0.0594 (9)
H70A0.99680.6360.10950.089*
H70B0.98290.68280.17870.089*
H70C0.88620.64390.12080.089*
C120.8865 (2)0.3484 (2)0.3748 (2)0.0659 (10)
H12A0.90790.40310.36710.099*
H12B0.92370.30980.35360.099*
H12C0.90120.33820.4270.099*
C410.8358 (2)0.6140 (2)0.43148 (15)0.0503 (7)
H41A0.86680.66210.45840.075*
H41B0.84560.56830.46490.075*
H41C0.76280.62320.40940.075*
C550.5746 (3)0.7973 (3)0.1534 (2)0.0811 (13)
H55A0.55370.78160.1960.122*
H55B0.51450.80030.11070.122*
H55C0.60790.84990.16190.122*
C451.0018 (2)0.5779 (2)0.40557 (15)0.0496 (7)
H45A1.03380.56880.36680.074*
H45B1.00980.52980.43620.074*
H45C1.03440.62370.43530.074*
C741.0914 (2)0.5443 (2)0.2283 (2)0.0683 (11)
H74A1.09980.49520.25750.103*
H74B1.11860.59010.260.103*
H74C1.12830.53890.19190.103*
H1030.470 (2)0.4615 (19)0.1073 (16)0.051 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S920.0203 (2)0.0228 (3)0.0183 (2)0.0030 (2)0.00325 (18)0.00112 (19)
Si910.0132 (2)0.0169 (3)0.0175 (2)0.0017 (2)0.00519 (19)0.0012 (2)
O900.0164 (6)0.0215 (7)0.0171 (6)0.0019 (5)0.0066 (5)0.0001 (5)
O880.0163 (7)0.0190 (7)0.0228 (7)0.0012 (5)0.0044 (5)0.0040 (6)
O890.0146 (6)0.0221 (7)0.0185 (6)0.0006 (5)0.0068 (5)0.0019 (5)
C600.0150 (9)0.0210 (10)0.0233 (9)0.0026 (8)0.0061 (7)0.0052 (8)
N1030.0275 (10)0.0316 (11)0.0321 (10)0.0047 (8)0.0144 (8)0.0000 (8)
C650.0258 (10)0.0246 (11)0.0173 (9)0.0025 (8)0.0070 (8)0.0012 (8)
C590.0157 (9)0.0186 (10)0.0163 (8)0.0033 (7)0.0064 (7)0.0038 (7)
C670.0180 (9)0.0193 (10)0.0179 (9)0.0011 (8)0.0048 (7)0.0020 (7)
C90.0218 (10)0.0287 (12)0.0305 (11)0.0004 (8)0.0142 (8)0.0001 (9)
C310.0204 (10)0.0261 (12)0.0299 (11)0.0018 (8)0.0043 (8)0.0106 (9)
C950.0322 (12)0.0297 (13)0.0522 (15)0.0023 (10)0.0154 (11)0.0139 (11)
C630.0282 (11)0.0340 (12)0.0207 (10)0.0056 (9)0.0133 (8)0.0034 (9)
C20.0223 (10)0.0276 (11)0.0227 (10)0.0007 (9)0.0088 (8)0.0033 (8)
C1010.0430 (14)0.0425 (15)0.0335 (12)0.0109 (11)0.0232 (11)0.0150 (11)
C10.0176 (9)0.0246 (11)0.0187 (9)0.0035 (8)0.0081 (7)0.0004 (8)
C800.0322 (12)0.0217 (11)0.0337 (11)0.0017 (9)0.0137 (9)0.0026 (9)
C780.0216 (10)0.0208 (10)0.0216 (9)0.0027 (8)0.0077 (8)0.0017 (8)
C680.0233 (10)0.0226 (11)0.0385 (12)0.0036 (8)0.0155 (9)0.0022 (9)
C100.0277 (11)0.0289 (12)0.0262 (10)0.0079 (9)0.0102 (9)0.0064 (9)
C610.0191 (10)0.0312 (12)0.0246 (10)0.0007 (8)0.0112 (8)0.0071 (9)
C70.0379 (13)0.0465 (15)0.0349 (12)0.0045 (11)0.0239 (10)0.0042 (11)
C30.0342 (12)0.0421 (14)0.0229 (11)0.0023 (10)0.0078 (9)0.0071 (10)
C320.0201 (11)0.0303 (13)0.0452 (13)0.0021 (9)0.0038 (10)0.0152 (11)
C930.0242 (11)0.0388 (14)0.0399 (13)0.0014 (10)0.0044 (10)0.0101 (11)
C380.0266 (11)0.0194 (11)0.0326 (11)0.0004 (8)0.0091 (9)0.0054 (9)
C300.0171 (9)0.0202 (10)0.0272 (10)0.0003 (8)0.0076 (8)0.0069 (8)
C290.0245 (11)0.0373 (14)0.0511 (14)0.0012 (10)0.0106 (10)0.0037 (11)
C490.0375 (13)0.0217 (11)0.0309 (11)0.0011 (9)0.0016 (9)0.0003 (9)
C200.0245 (11)0.0305 (12)0.0403 (12)0.0068 (9)0.0161 (9)0.0006 (10)
C390.0269 (12)0.0315 (13)0.0341 (12)0.0004 (10)0.0060 (9)0.0038 (10)
C990.0271 (12)0.074 (2)0.0351 (13)0.0169 (12)0.0116 (10)0.0199 (13)
C360.0406 (13)0.0203 (12)0.0440 (13)0.0029 (10)0.0140 (11)0.0021 (10)
C160.0518 (16)0.0361 (14)0.0411 (14)0.0012 (12)0.0178 (12)0.0005 (11)
C970.0215 (11)0.0511 (16)0.0462 (14)0.0039 (11)0.0122 (10)0.0015 (12)
C50.0456 (15)0.0583 (18)0.0211 (11)0.0003 (12)0.0161 (10)0.0003 (11)
C840.0240 (11)0.0268 (12)0.0290 (11)0.0058 (9)0.0049 (9)0.0048 (9)
C220.0302 (13)0.0333 (15)0.077 (2)0.0046 (11)0.0111 (13)0.0021 (13)
C340.0328 (12)0.0277 (13)0.0565 (15)0.0115 (10)0.0173 (11)0.0150 (11)
C510.052 (2)0.160 (4)0.0393 (17)0.002 (2)0.0048 (14)0.023 (2)
C700.113 (3)0.0236 (14)0.0606 (18)0.0038 (15)0.0550 (19)0.0018 (13)
C120.0281 (14)0.0489 (19)0.118 (3)0.0043 (13)0.0173 (16)0.0282 (19)
C410.0365 (14)0.068 (2)0.0446 (15)0.0017 (13)0.0088 (12)0.0127 (14)
C550.0396 (17)0.117 (3)0.069 (2)0.0280 (19)0.0128 (16)0.029 (2)
C450.0371 (15)0.0613 (19)0.0412 (14)0.0154 (13)0.0029 (11)0.0023 (13)
C740.0250 (13)0.064 (2)0.106 (3)0.0087 (13)0.0031 (15)0.051 (2)
Geometric parameters (Å, º) top
S92—Si912.0286 (7)C93—H930.93
Si91—O881.6502 (14)C38—C361.399 (3)
Si91—O901.6561 (14)C38—C301.400 (3)
Si91—O891.6580 (14)C38—C491.526 (3)
O90—C11.395 (2)C29—C201.526 (3)
O88—C301.383 (2)C29—H29A0.96
O89—C591.382 (2)C29—H29B0.96
C60—C611.393 (3)C29—H29C0.96
C60—C591.405 (3)C49—C511.498 (4)
C60—C681.512 (3)C49—C551.523 (4)
N103—C1011.323 (3)C49—H490.98
N103—C931.331 (3)C20—C221.520 (4)
N103—H1030.93 (3)C20—H200.98
C65—C631.384 (3)C39—C411.513 (4)
C65—C671.393 (3)C39—C451.524 (3)
C65—H650.93C39—H390.98
C59—C671.411 (3)C99—C971.370 (4)
C67—C781.520 (3)C99—H990.93
C9—C11.397 (3)C36—C341.378 (4)
C9—C71.399 (3)C36—H360.93
C9—C201.518 (3)C16—H16A0.96
C31—C321.395 (3)C16—H16B0.96
C31—C301.410 (3)C16—H16C0.96
C31—C391.514 (3)C97—H970.93
C95—C931.370 (3)C5—H50.93
C95—C971.373 (3)C84—H84A0.96
C95—H950.93C84—H84B0.96
C63—C611.382 (3)C84—H84C0.96
C63—H630.93C22—H22A0.96
C2—C31.394 (3)C22—H22B0.96
C2—C11.404 (3)C22—H22C0.96
C2—C101.518 (3)C34—H340.93
C101—C991.374 (4)C51—H51A0.96
C101—H1010.93C51—H51B0.96
C80—C781.535 (3)C51—H51C0.96
C80—H80A0.96C70—H70A0.96
C80—H80B0.96C70—H70B0.96
C80—H80C0.96C70—H70C0.96
C78—C841.531 (3)C12—H12A0.96
C78—H780.98C12—H12B0.96
C68—C701.515 (3)C12—H12C0.96
C68—C741.522 (3)C41—H41A0.96
C68—H680.98C41—H41B0.96
C10—C121.518 (3)C41—H41C0.96
C10—C161.524 (3)C55—H55A0.96
C10—H100.98C55—H55B0.96
C61—H610.93C55—H55C0.96
C7—C51.385 (4)C45—H45A0.96
C7—H70.93C45—H45B0.96
C3—C51.376 (4)C45—H45C0.96
C3—H30.93C74—H74A0.96
C32—C341.379 (4)C74—H74B0.96
C32—H320.93C74—H74C0.96
O88—Si91—O90102.16 (7)H29B—C29—H29C109.5
O88—Si91—O89106.70 (7)C51—C49—C55110.7 (3)
O90—Si91—O89105.69 (7)C51—C49—C38113.1 (2)
O88—Si91—S92116.74 (6)C55—C49—C38111.4 (2)
O90—Si91—S92111.12 (5)C51—C49—H49107.1
O89—Si91—S92113.32 (5)C55—C49—H49107.1
C1—O90—Si91130.13 (12)C38—C49—H49107.1
C30—O88—Si91135.01 (13)C9—C20—C22111.3 (2)
C59—O89—Si91129.35 (11)C9—C20—C29111.6 (2)
C61—C60—C59118.10 (19)C22—C20—C29111.0 (2)
C61—C60—C68120.07 (18)C9—C20—H20107.6
C59—C60—C68121.83 (18)C22—C20—H20107.6
C101—N103—C93122.3 (2)C29—C20—H20107.6
C101—N103—H103118.3 (18)C41—C39—C31110.4 (2)
C93—N103—H103119.4 (18)C41—C39—C45110.2 (2)
C63—C65—C67122.1 (2)C31—C39—C45113.6 (2)
C63—C65—H65118.9C41—C39—H39107.5
C67—C65—H65118.9C31—C39—H39107.5
O89—C59—C60117.59 (17)C45—C39—H39107.5
O89—C59—C67120.98 (17)C97—C99—C101119.5 (2)
C60—C59—C67121.35 (17)C97—C99—H99120.2
C65—C67—C59117.55 (18)C101—C99—H99120.2
C65—C67—C78118.83 (18)C34—C36—C38121.6 (2)
C59—C67—C78123.43 (17)C34—C36—H36119.2
C1—C9—C7117.3 (2)C38—C36—H36119.2
C1—C9—C20122.39 (19)C10—C16—H16A109.5
C7—C9—C20120.3 (2)C10—C16—H16B109.5
C32—C31—C30117.4 (2)H16A—C16—H16B109.5
C32—C31—C39121.22 (19)C10—C16—H16C109.5
C30—C31—C39121.3 (2)H16A—C16—H16C109.5
C93—C95—C97119.0 (2)H16B—C16—H16C109.5
C93—C95—H95120.5C99—C97—C95119.6 (2)
C97—C95—H95120.5C99—C97—H97120.2
C61—C63—C65119.03 (19)C95—C97—H97120.2
C61—C63—H63120.5C3—C5—C7119.5 (2)
C65—C63—H63120.5C3—C5—H5120.3
C3—C2—C1117.4 (2)C7—C5—H5120.3
C3—C2—C10120.36 (19)C78—C84—H84A109.5
C1—C2—C10122.16 (18)C78—C84—H84B109.5
N103—C101—C99119.5 (2)H84A—C84—H84B109.5
N103—C101—H101120.2C78—C84—H84C109.5
C99—C101—H101120.2H84A—C84—H84C109.5
O90—C1—C9118.59 (17)H84B—C84—H84C109.5
O90—C1—C2118.88 (18)C20—C22—H22A109.5
C9—C1—C2122.41 (18)C20—C22—H22B109.5
C78—C80—H80A109.5H22A—C22—H22B109.5
C78—C80—H80B109.5C20—C22—H22C109.5
H80A—C80—H80B109.5H22A—C22—H22C109.5
C78—C80—H80C109.5H22B—C22—H22C109.5
H80A—C80—H80C109.5C36—C34—C32119.9 (2)
H80B—C80—H80C109.5C36—C34—H34120.1
C67—C78—C84113.03 (17)C32—C34—H34120.1
C67—C78—C80109.19 (16)C49—C51—H51A109.5
C84—C78—C80110.44 (17)C49—C51—H51B109.5
C67—C78—H78108H51A—C51—H51B109.5
C84—C78—H78108C49—C51—H51C109.5
C80—C78—H78108H51A—C51—H51C109.5
C60—C68—C70111.4 (2)H51B—C51—H51C109.5
C60—C68—C74111.50 (19)C68—C70—H70A109.5
C70—C68—C74111.4 (3)C68—C70—H70B109.5
C60—C68—H68107.4H70A—C70—H70B109.5
C70—C68—H68107.4C68—C70—H70C109.5
C74—C68—H68107.4H70A—C70—H70C109.5
C2—C10—C12112.6 (2)H70B—C70—H70C109.5
C2—C10—C16110.95 (19)C10—C12—H12A109.5
C12—C10—C16110.4 (2)C10—C12—H12B109.5
C2—C10—H10107.5H12A—C12—H12B109.5
C12—C10—H10107.5C10—C12—H12C109.5
C16—C10—H10107.5H12A—C12—H12C109.5
C63—C61—C60121.77 (19)H12B—C12—H12C109.5
C63—C61—H61119.1C39—C41—H41A109.5
C60—C61—H61119.1C39—C41—H41B109.5
C5—C7—C9121.6 (2)H41A—C41—H41B109.5
C5—C7—H7119.2C39—C41—H41C109.5
C9—C7—H7119.2H41A—C41—H41C109.5
C5—C3—C2121.8 (2)H41B—C41—H41C109.5
C5—C3—H3119.1C49—C55—H55A109.5
C2—C3—H3119.1C49—C55—H55B109.5
C34—C32—C31121.5 (2)H55A—C55—H55B109.5
C34—C32—H32119.2C49—C55—H55C109.5
C31—C32—H32119.2H55A—C55—H55C109.5
N103—C93—C95120.1 (2)H55B—C55—H55C109.5
N103—C93—H93120C39—C45—H45A109.5
C95—C93—H93120C39—C45—H45B109.5
C36—C38—C30117.4 (2)H45A—C45—H45B109.5
C36—C38—C49120.0 (2)C39—C45—H45C109.5
C30—C38—C49122.62 (19)H45A—C45—H45C109.5
O88—C30—C38120.94 (17)H45B—C45—H45C109.5
O88—C30—C31116.78 (19)C68—C74—H74A109.5
C38—C30—C31122.1 (2)C68—C74—H74B109.5
C20—C29—H29A109.5H74A—C74—H74B109.5
C20—C29—H29B109.5C68—C74—H74C109.5
H29A—C29—H29B109.5H74A—C74—H74C109.5
C20—C29—H29C109.5H74B—C74—H74C109.5
H29A—C29—H29C109.5
O88—Si91—O90—C126.66 (17)C1—C2—C10—C16112.8 (2)
O89—Si91—O90—C184.80 (17)C65—C63—C61—C601.6 (3)
S92—Si91—O90—C1151.87 (14)C59—C60—C61—C630.1 (3)
O90—Si91—O88—C30159.39 (17)C68—C60—C61—C63179.31 (19)
O89—Si91—O88—C3048.68 (19)C1—C9—C7—C50.3 (4)
S92—Si91—O88—C3079.20 (18)C20—C9—C7—C5179.4 (2)
O88—Si91—O89—C59129.18 (16)C1—C2—C3—C50.8 (4)
O90—Si91—O89—C59122.60 (16)C10—C2—C3—C5176.2 (2)
S92—Si91—O89—C590.68 (17)C30—C31—C32—C341.8 (3)
Si91—O89—C59—C60113.98 (17)C39—C31—C32—C34175.7 (2)
Si91—O89—C59—C6769.4 (2)C101—N103—C93—C950.3 (4)
C61—C60—C59—O89179.24 (16)C97—C95—C93—N1031.5 (4)
C68—C60—C59—O890.2 (3)Si91—O88—C30—C3883.3 (2)
C61—C60—C59—C672.6 (3)Si91—O88—C30—C31101.0 (2)
C68—C60—C59—C67176.80 (18)C36—C38—C30—O88177.51 (19)
C63—C65—C67—C591.5 (3)C49—C38—C30—O881.3 (3)
C63—C65—C67—C78173.67 (18)C36—C38—C30—C312.0 (3)
O89—C59—C67—C65179.79 (17)C49—C38—C30—C31176.8 (2)
C60—C59—C67—C653.3 (3)C32—C31—C30—O88178.35 (18)
O89—C59—C67—C784.8 (3)C39—C31—C30—O880.9 (3)
C60—C59—C67—C78171.67 (18)C32—C31—C30—C382.7 (3)
C67—C65—C63—C610.9 (3)C39—C31—C30—C38174.7 (2)
C93—N103—C101—C990.8 (4)C36—C38—C49—C5155.7 (3)
Si91—O90—C1—C987.2 (2)C30—C38—C49—C51125.4 (3)
Si91—O90—C1—C296.8 (2)C36—C38—C49—C5569.7 (3)
C7—C9—C1—O90177.37 (19)C30—C38—C49—C55109.1 (3)
C20—C9—C1—O901.8 (3)C1—C9—C20—C22123.6 (2)
C7—C9—C1—C21.5 (3)C7—C9—C20—C2257.3 (3)
C20—C9—C1—C2177.7 (2)C1—C9—C20—C29111.9 (2)
C3—C2—C1—O90177.87 (19)C7—C9—C20—C2967.2 (3)
C10—C2—C1—O901.0 (3)C32—C31—C39—C4189.8 (3)
C3—C2—C1—C92.0 (3)C30—C31—C39—C4187.5 (3)
C10—C2—C1—C9174.9 (2)C32—C31—C39—C4534.5 (3)
C65—C67—C78—C8454.7 (2)C30—C31—C39—C45148.2 (2)
C59—C67—C78—C84130.4 (2)N103—C101—C99—C970.6 (4)
C65—C67—C78—C8068.6 (2)C30—C38—C36—C340.4 (4)
C59—C67—C78—C80106.3 (2)C49—C38—C36—C34178.5 (2)
C61—C60—C68—C7069.9 (3)C101—C99—C97—C950.6 (4)
C59—C60—C68—C70110.7 (2)C93—C95—C97—C991.6 (4)
C61—C60—C68—C7455.2 (3)C2—C3—C5—C70.9 (4)
C59—C60—C68—C74124.2 (3)C9—C7—C5—C31.4 (4)
C3—C2—C10—C1260.3 (3)C38—C36—C34—C320.5 (4)
C1—C2—C10—C12122.9 (3)C31—C32—C34—C360.2 (4)
C3—C2—C10—C1664.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N103—H103···S920.93 (3)2.11 (3)3.024 (2)167 (3)
(tdst_py_150) top
Crystal data top
C36H51O3SSi·C5H6NF(000) = 1456
Mr = 672.02Dx = 1.126 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 17688 reflections
a = 13.4625 (6) Åθ = 3.4–29.4°
b = 16.3181 (5) ŵ = 0.15 mm1
c = 18.8624 (8) ÅT = 150 K
β = 106.983 (3)°Plate, colorless
V = 3963.0 (3) Å30.38 × 0.31 × 0.15 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
5331 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.049
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.1°
rotation method scansh = 1613
22240 measured reflectionsk = 1920
7758 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.063P)2 + 0.4461P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
7758 reflectionsΔρmax = 0.50 e Å3
440 parametersΔρmin = 0.33 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S920.59552 (4)0.52625 (3)0.09033 (3)0.02977 (13)
Si910.68597 (4)0.51559 (3)0.19646 (3)0.02237 (13)
O900.63001 (10)0.45687 (9)0.24520 (7)0.0255 (3)
O880.70918 (10)0.60024 (9)0.24582 (7)0.0276 (3)
O890.80002 (10)0.47280 (9)0.20390 (7)0.0254 (3)
C600.92779 (15)0.48645 (13)0.14028 (11)0.0277 (4)
N1030.40577 (16)0.43769 (14)0.10528 (11)0.0405 (5)
C650.84637 (17)0.35141 (14)0.05295 (11)0.0322 (5)
H650.81970.30630.02350.039*
C590.84112 (15)0.44543 (12)0.14920 (10)0.0239 (4)
C670.80049 (15)0.37562 (13)0.10711 (10)0.0256 (4)
C90.57326 (18)0.50879 (15)0.34581 (13)0.0375 (5)
C310.86574 (17)0.66576 (15)0.31464 (13)0.0372 (5)
C950.3108 (2)0.33654 (18)0.14292 (17)0.0545 (7)
H950.30820.29150.17260.065*
C630.93018 (17)0.39253 (15)0.04191 (12)0.0359 (5)
H630.95910.37560.00520.043*
C20.70701 (18)0.40186 (15)0.36717 (12)0.0345 (5)
C1010.3216 (2)0.46920 (19)0.05956 (14)0.0511 (7)
H1010.3260.51530.03160.061*
C10.63841 (16)0.45715 (13)0.32060 (11)0.0282 (4)
C800.7644 (2)0.24126 (15)0.15647 (14)0.0415 (6)
H80A0.78970.21090.12170.062*
H80B0.71250.20960.16990.062*
H80C0.82080.25270.20.062*
C780.71648 (16)0.32215 (13)0.12097 (11)0.0288 (4)
H780.68810.35060.15650.035*
C680.97582 (17)0.55880 (14)0.18862 (13)0.0361 (5)
H680.93950.56490.22640.043*
C100.77064 (19)0.34151 (15)0.33829 (13)0.0399 (6)
H100.75780.35260.28530.048*
C610.97049 (17)0.45896 (14)0.08605 (12)0.0336 (5)
H611.02780.48610.07930.04*
C70.5812 (2)0.50460 (19)0.42156 (15)0.0536 (7)
H70.53870.53780.44020.064*
C30.7113 (2)0.40198 (18)0.44186 (13)0.0481 (6)
H30.75690.36650.47420.058*
C320.93214 (19)0.73219 (16)0.32308 (15)0.0467 (6)
H320.99240.73310.36280.056*
C930.40329 (19)0.37290 (17)0.14667 (15)0.0494 (7)
H930.46460.35210.17830.059*
C380.75226 (18)0.73130 (14)0.20325 (13)0.0361 (5)
C300.77624 (16)0.66583 (13)0.25280 (12)0.0291 (5)
C290.3847 (2)0.53915 (19)0.28675 (18)0.0573 (7)
H29A0.37470.4840.26830.086*
H29B0.33760.5750.25260.086*
H29C0.37180.54170.33410.086*
C490.6529 (2)0.73420 (16)0.13837 (14)0.0461 (6)
H490.62040.680.13460.055*
C200.49605 (18)0.56564 (16)0.29500 (15)0.0427 (6)
H200.50690.56240.24590.051*
C390.8858 (2)0.59767 (17)0.37126 (14)0.0473 (7)
H390.8520.54810.34610.057*
C990.2270 (2)0.4338 (2)0.05317 (15)0.0610 (8)
H990.1670.45530.02050.073*
C360.8219 (2)0.79648 (16)0.21534 (16)0.0485 (6)
H360.80780.84080.18290.058*
C160.7356 (3)0.25384 (19)0.34557 (18)0.0634 (8)
H16A0.74890.24050.39710.095*
H16B0.77330.21690.32330.095*
H16C0.66260.2490.32090.095*
C970.2216 (2)0.3671 (2)0.09497 (16)0.0550 (7)
H970.15790.34250.0910.066*
C50.6502 (2)0.4527 (2)0.46907 (14)0.0583 (8)
H50.65530.45220.51930.07*
C840.62666 (18)0.30549 (16)0.05096 (13)0.0404 (6)
H84A0.59810.35660.0290.061*
H84B0.57380.27440.06380.061*
H84C0.65180.2750.01620.061*
C220.5137 (2)0.65376 (19)0.3207 (2)0.0683 (9)
H22A0.50490.65870.36920.102*
H22B0.46440.68840.28680.102*
H22C0.58290.670.32240.102*
C340.9113 (2)0.79689 (17)0.27425 (17)0.0525 (7)
H340.95720.84070.28090.063*
C510.6724 (3)0.7514 (4)0.0657 (2)0.1177 (19)
H51A0.7020.80510.06690.177*
H51B0.6080.74890.02670.177*
H51C0.71960.71130.05690.177*
C700.9606 (4)0.63716 (19)0.1445 (2)0.0829 (12)
H70A1.00010.63490.10950.124*
H70B0.98380.68270.17740.124*
H70C0.88830.64380.11840.124*
C120.8856 (2)0.3496 (2)0.3744 (3)0.0913 (14)
H12A0.90720.40440.36790.137*
H12B0.92190.31160.35210.137*
H12C0.90110.33780.42640.137*
C410.8371 (3)0.6176 (3)0.43166 (19)0.0745 (10)
H41A0.86810.66640.4570.112*
H41B0.84820.57290.46620.112*
H41C0.76390.62620.41020.112*
C550.5761 (3)0.7956 (3)0.1521 (2)0.1112 (18)
H55A0.56040.78180.19710.167*
H55B0.51340.79440.11140.167*
H55C0.60570.84950.15640.167*
C451.0006 (2)0.5784 (2)0.40479 (17)0.0710 (10)
H45A1.03190.56910.36580.106*
H45B1.00810.53020.43510.106*
H45C1.03440.62370.43460.106*
C741.0892 (2)0.5439 (3)0.2286 (3)0.0959 (15)
H74A1.0960.49490.25780.144*
H74B1.11660.58960.26030.144*
H74C1.1270.53760.19290.144*
H1030.465 (2)0.4623 (18)0.1052 (15)0.053 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S920.0284 (3)0.0330 (3)0.0259 (2)0.0044 (2)0.00491 (19)0.0017 (2)
Si910.0194 (3)0.0245 (3)0.0238 (2)0.0016 (2)0.0073 (2)0.0013 (2)
O900.0238 (7)0.0295 (8)0.0245 (6)0.0016 (6)0.0092 (5)0.0011 (6)
O880.0234 (7)0.0275 (8)0.0316 (7)0.0039 (6)0.0075 (6)0.0065 (6)
O890.0204 (6)0.0323 (8)0.0249 (6)0.0008 (6)0.0087 (5)0.0017 (6)
C600.0224 (10)0.0297 (11)0.0329 (10)0.0018 (8)0.0110 (8)0.0060 (9)
N1030.0355 (11)0.0439 (12)0.0476 (12)0.0080 (10)0.0206 (9)0.0012 (9)
C650.0356 (12)0.0357 (13)0.0265 (10)0.0008 (9)0.0109 (9)0.0031 (9)
C590.0222 (9)0.0272 (11)0.0237 (9)0.0044 (8)0.0088 (7)0.0034 (8)
C670.0249 (10)0.0280 (11)0.0243 (9)0.0017 (8)0.0077 (8)0.0025 (8)
C90.0357 (12)0.0412 (14)0.0422 (12)0.0003 (10)0.0216 (10)0.0022 (10)
C310.0294 (11)0.0365 (13)0.0429 (12)0.0014 (10)0.0064 (9)0.0122 (10)
C950.0467 (15)0.0451 (16)0.0746 (19)0.0030 (12)0.0220 (14)0.0226 (14)
C630.0360 (12)0.0468 (14)0.0314 (11)0.0064 (10)0.0201 (9)0.0023 (10)
C20.0355 (12)0.0403 (13)0.0299 (10)0.0004 (10)0.0130 (9)0.0043 (9)
C1010.0576 (16)0.0597 (18)0.0459 (14)0.0109 (14)0.0305 (12)0.0203 (13)
C10.0261 (10)0.0342 (12)0.0279 (10)0.0023 (8)0.0132 (8)0.0002 (8)
C800.0439 (14)0.0346 (13)0.0507 (14)0.0032 (11)0.0213 (11)0.0053 (11)
C780.0291 (11)0.0280 (11)0.0317 (10)0.0039 (9)0.0125 (9)0.0017 (8)
C680.0306 (11)0.0322 (12)0.0509 (13)0.0062 (9)0.0203 (10)0.0059 (10)
C100.0430 (13)0.0419 (14)0.0360 (12)0.0126 (11)0.0136 (10)0.0101 (10)
C610.0294 (11)0.0398 (13)0.0369 (11)0.0021 (9)0.0182 (9)0.0065 (10)
C70.0596 (17)0.0669 (19)0.0478 (14)0.0052 (14)0.0366 (13)0.0071 (13)
C30.0524 (15)0.0618 (18)0.0307 (12)0.0051 (13)0.0129 (11)0.0091 (11)
C320.0316 (12)0.0425 (15)0.0608 (16)0.0035 (11)0.0056 (11)0.0195 (13)
C930.0329 (13)0.0528 (17)0.0586 (16)0.0019 (11)0.0072 (11)0.0174 (13)
C380.0357 (12)0.0292 (12)0.0440 (12)0.0005 (9)0.0127 (10)0.0048 (10)
C300.0261 (10)0.0266 (11)0.0369 (11)0.0008 (8)0.0126 (9)0.0091 (9)
C290.0382 (14)0.0532 (18)0.082 (2)0.0023 (12)0.0193 (14)0.0025 (15)
C490.0549 (16)0.0299 (13)0.0459 (14)0.0032 (11)0.0026 (11)0.0021 (11)
C200.0347 (12)0.0430 (14)0.0569 (15)0.0076 (11)0.0235 (11)0.0011 (12)
C390.0416 (14)0.0435 (15)0.0439 (13)0.0003 (11)0.0077 (11)0.0048 (11)
C990.0358 (14)0.099 (3)0.0499 (15)0.0187 (15)0.0156 (12)0.0258 (16)
C360.0575 (16)0.0305 (13)0.0601 (16)0.0075 (12)0.0211 (13)0.0024 (12)
C160.082 (2)0.0497 (18)0.0639 (18)0.0020 (16)0.0300 (16)0.0007 (15)
C970.0319 (13)0.070 (2)0.0657 (17)0.0059 (13)0.0182 (12)0.0062 (15)
C50.0707 (19)0.079 (2)0.0313 (12)0.0035 (16)0.0243 (12)0.0008 (13)
C840.0376 (13)0.0407 (14)0.0424 (12)0.0099 (10)0.0109 (10)0.0080 (10)
C220.0481 (16)0.0472 (18)0.110 (3)0.0069 (14)0.0232 (17)0.0050 (17)
C340.0486 (15)0.0372 (15)0.0748 (19)0.0180 (12)0.0230 (14)0.0201 (14)
C510.083 (3)0.211 (6)0.052 (2)0.009 (3)0.0088 (19)0.033 (3)
C700.157 (4)0.0335 (16)0.084 (2)0.009 (2)0.076 (2)0.0045 (16)
C120.0405 (17)0.077 (3)0.151 (4)0.0133 (16)0.019 (2)0.037 (3)
C410.059 (2)0.097 (3)0.069 (2)0.0060 (18)0.0196 (16)0.0229 (19)
C550.058 (2)0.156 (5)0.097 (3)0.037 (3)0.013 (2)0.037 (3)
C450.0545 (19)0.089 (3)0.0574 (17)0.0221 (17)0.0020 (14)0.0033 (17)
C740.0342 (16)0.097 (3)0.138 (3)0.0080 (17)0.0031 (19)0.068 (3)
Geometric parameters (Å, º) top
S92—Si912.0239 (7)C93—H930.93
Si91—O881.6439 (14)C38—C361.392 (3)
Si91—O901.6540 (14)C38—C301.394 (3)
Si91—O891.6550 (14)C38—C491.528 (3)
O90—C11.393 (2)C29—C201.523 (4)
O88—C301.381 (3)C29—H29A0.96
O89—C591.380 (2)C29—H29B0.96
C60—C611.386 (3)C29—H29C0.96
C60—C591.397 (3)C49—C511.495 (5)
C60—C681.516 (3)C49—C551.515 (5)
N103—C1011.312 (3)C49—H490.98
N103—C931.321 (3)C20—C221.514 (4)
N103—H1030.89 (3)C20—H200.98
C65—C631.380 (3)C39—C411.507 (4)
C65—C671.396 (3)C39—C451.522 (4)
C65—H650.93C39—H390.98
C59—C671.405 (3)C99—C971.358 (4)
C67—C781.510 (3)C99—H990.93
C9—C11.396 (3)C36—C341.379 (4)
C9—C71.403 (3)C36—H360.93
C9—C201.509 (3)C16—H16A0.96
C31—C321.384 (4)C16—H16B0.96
C31—C301.411 (3)C16—H16C0.96
C31—C391.510 (4)C97—H970.93
C95—C931.363 (4)C5—H50.93
C95—C971.369 (4)C84—H84A0.96
C95—H950.93C84—H84B0.96
C63—C611.378 (3)C84—H84C0.96
C63—H630.93C22—H22A0.96
C2—C31.393 (3)C22—H22B0.96
C2—C11.402 (3)C22—H22C0.96
C2—C101.508 (3)C34—H340.93
C101—C991.371 (4)C51—H51A0.96
C101—H1010.93C51—H51B0.96
C80—C781.534 (3)C51—H51C0.96
C80—H80A0.96C70—H70A0.96
C80—H80B0.96C70—H70B0.96
C80—H80C0.96C70—H70C0.96
C78—C841.532 (3)C12—H12A0.96
C78—H780.98C12—H12B0.96
C68—C701.507 (4)C12—H12C0.96
C68—C741.511 (4)C41—H41A0.96
C68—H680.98C41—H41B0.96
C10—C121.504 (4)C41—H41C0.96
C10—C161.525 (4)C55—H55A0.96
C10—H100.98C55—H55B0.96
C61—H610.93C55—H55C0.96
C7—C51.377 (4)C45—H45A0.96
C7—H70.93C45—H45B0.96
C3—C51.368 (4)C45—H45C0.96
C3—H30.93C74—H74A0.96
C32—C341.375 (4)C74—H74B0.96
C32—H320.93C74—H74C0.96
O88—Si91—O90102.36 (7)H29B—C29—H29C109.5
O88—Si91—O89106.76 (7)C51—C49—C55110.1 (3)
O90—Si91—O89105.68 (7)C51—C49—C38113.1 (3)
O88—Si91—S92116.61 (6)C55—C49—C38111.4 (2)
O90—Si91—S92111.07 (5)C51—C49—H49107.3
O89—Si91—S92113.29 (5)C55—C49—H49107.3
C1—O90—Si91130.63 (13)C38—C49—H49107.3
C30—O88—Si91135.71 (13)C9—C20—C22111.5 (2)
C59—O89—Si91129.64 (12)C9—C20—C29111.4 (2)
C61—C60—C59118.3 (2)C22—C20—C29111.1 (2)
C61—C60—C68119.99 (19)C9—C20—H20107.6
C59—C60—C68121.67 (19)C22—C20—H20107.6
C101—N103—C93122.4 (2)C29—C20—H20107.6
C101—N103—H103115.0 (18)C41—C39—C31110.4 (2)
C93—N103—H103122.6 (19)C41—C39—C45110.1 (2)
C63—C65—C67121.9 (2)C31—C39—C45113.3 (3)
C63—C65—H65119C41—C39—H39107.6
C67—C65—H65119C31—C39—H39107.6
O89—C59—C60117.81 (18)C45—C39—H39107.6
O89—C59—C67120.67 (17)C97—C99—C101119.5 (2)
C60—C59—C67121.42 (18)C97—C99—H99120.3
C65—C67—C59117.42 (19)C101—C99—H99120.3
C65—C67—C78118.48 (19)C34—C36—C38121.5 (3)
C59—C67—C78123.92 (18)C34—C36—H36119.2
C1—C9—C7116.7 (2)C38—C36—H36119.2
C1—C9—C20122.6 (2)C10—C16—H16A109.5
C7—C9—C20120.7 (2)C10—C16—H16B109.5
C32—C31—C30117.5 (2)H16A—C16—H16B109.5
C32—C31—C39121.2 (2)C10—C16—H16C109.5
C30—C31—C39121.2 (2)H16A—C16—H16C109.5
C93—C95—C97119.2 (3)H16B—C16—H16C109.5
C93—C95—H95120.4C99—C97—C95119.4 (3)
C97—C95—H95120.4C99—C97—H97120.3
C61—C63—C65119.1 (2)C95—C97—H97120.3
C61—C63—H63120.4C3—C5—C7119.5 (2)
C65—C63—H63120.4C3—C5—H5120.2
C3—C2—C1117.2 (2)C7—C5—H5120.2
C3—C2—C10120.4 (2)C78—C84—H84A109.5
C1—C2—C10122.27 (19)C78—C84—H84B109.5
N103—C101—C99119.7 (3)H84A—C84—H84B109.5
N103—C101—H101120.2C78—C84—H84C109.5
C99—C101—H101120.2H84A—C84—H84C109.5
O90—C1—C9118.54 (19)H84B—C84—H84C109.5
O90—C1—C2118.68 (19)C20—C22—H22A109.5
C9—C1—C2122.7 (2)C20—C22—H22B109.5
C78—C80—H80A109.5H22A—C22—H22B109.5
C78—C80—H80B109.5C20—C22—H22C109.5
H80A—C80—H80B109.5H22A—C22—H22C109.5
C78—C80—H80C109.5H22B—C22—H22C109.5
H80A—C80—H80C109.5C32—C34—C36119.7 (2)
H80B—C80—H80C109.5C32—C34—H34120.1
C67—C78—C84113.30 (18)C36—C34—H34120.1
C67—C78—C80109.40 (18)C49—C51—H51A109.5
C84—C78—C80110.41 (19)C49—C51—H51B109.5
C67—C78—H78107.8H51A—C51—H51B109.5
C84—C78—H78107.8C49—C51—H51C109.5
C80—C78—H78107.8H51A—C51—H51C109.5
C70—C68—C74111.5 (3)H51B—C51—H51C109.5
C70—C68—C60111.3 (2)C68—C70—H70A109.5
C74—C68—C60111.4 (2)C68—C70—H70B109.5
C70—C68—H68107.5H70A—C70—H70B109.5
C74—C68—H68107.5C68—C70—H70C109.5
C60—C68—H68107.5H70A—C70—H70C109.5
C12—C10—C2113.4 (2)H70B—C70—H70C109.5
C12—C10—C16110.2 (3)C10—C12—H12A109.5
C2—C10—C16110.9 (2)C10—C12—H12B109.5
C12—C10—H10107.3H12A—C12—H12B109.5
C2—C10—H10107.3C10—C12—H12C109.5
C16—C10—H10107.3H12A—C12—H12C109.5
C63—C61—C60121.7 (2)H12B—C12—H12C109.5
C63—C61—H61119.2C39—C41—H41A109.5
C60—C61—H61119.2C39—C41—H41B109.5
C5—C7—C9122.0 (3)H41A—C41—H41B109.5
C5—C7—H7119C39—C41—H41C109.5
C9—C7—H7119H41A—C41—H41C109.5
C5—C3—C2121.9 (2)H41B—C41—H41C109.5
C5—C3—H3119C49—C55—H55A109.5
C2—C3—H3119C49—C55—H55B109.5
C34—C32—C31121.7 (2)H55A—C55—H55B109.5
C34—C32—H32119.2C49—C55—H55C109.5
C31—C32—H32119.2H55A—C55—H55C109.5
N103—C93—C95119.9 (2)H55B—C55—H55C109.5
N103—C93—H93120.1C39—C45—H45A109.5
C95—C93—H93120.1C39—C45—H45B109.5
C36—C38—C30117.6 (2)H45A—C45—H45B109.5
C36—C38—C49119.9 (2)C39—C45—H45C109.5
C30—C38—C49122.5 (2)H45A—C45—H45C109.5
O88—C30—C38120.86 (18)H45B—C45—H45C109.5
O88—C30—C31117.0 (2)C68—C74—H74A109.5
C38—C30—C31122.0 (2)C68—C74—H74B109.5
C20—C29—H29A109.5H74A—C74—H74B109.5
C20—C29—H29B109.5C68—C74—H74C109.5
H29A—C29—H29B109.5H74A—C74—H74C109.5
C20—C29—H29C109.5H74B—C74—H74C109.5
H29A—C29—H29C109.5
O88—Si91—O90—C126.15 (18)C1—C2—C10—C16112.7 (3)
O89—Si91—O90—C185.45 (17)C65—C63—C61—C601.2 (3)
S92—Si91—O90—C1151.30 (15)C59—C60—C61—C630.6 (3)
O90—Si91—O88—C30158.28 (18)C68—C60—C61—C63178.8 (2)
O89—Si91—O88—C3047.5 (2)C1—C9—C7—C50.5 (4)
S92—Si91—O88—C3080.29 (19)C20—C9—C7—C5179.3 (3)
O88—Si91—O89—C59128.60 (16)C1—C2—C3—C51.0 (4)
O90—Si91—O89—C59122.93 (16)C10—C2—C3—C5176.3 (3)
S92—Si91—O89—C591.10 (18)C30—C31—C32—C341.4 (4)
Si91—O89—C59—C60113.97 (18)C39—C31—C32—C34176.0 (2)
Si91—O89—C59—C6769.7 (2)C101—N103—C93—C950.2 (4)
C61—C60—C59—O89179.30 (17)C97—C95—C93—N1031.2 (5)
C68—C60—C59—O890.1 (3)Si91—O88—C30—C3883.2 (3)
C61—C60—C59—C673.0 (3)Si91—O88—C30—C31100.9 (2)
C68—C60—C59—C67176.37 (19)C36—C38—C30—O88177.8 (2)
C63—C65—C67—C591.7 (3)C49—C38—C30—O881.0 (3)
C63—C65—C67—C78173.7 (2)C36—C38—C30—C312.0 (3)
O89—C59—C67—C65179.73 (17)C49—C38—C30—C31176.8 (2)
C60—C59—C67—C653.6 (3)C32—C31—C30—O88178.5 (2)
O89—C59—C67—C784.6 (3)C39—C31—C30—O881.2 (3)
C60—C59—C67—C78171.55 (19)C32—C31—C30—C382.6 (3)
C67—C65—C63—C610.6 (3)C39—C31—C30—C38174.8 (2)
C93—N103—C101—C990.8 (4)C36—C38—C49—C5153.1 (4)
Si91—O90—C1—C986.7 (2)C30—C38—C49—C51128.1 (3)
Si91—O90—C1—C297.3 (2)C36—C38—C49—C5571.6 (4)
C7—C9—C1—O90177.4 (2)C30—C38—C49—C55107.2 (3)
C20—C9—C1—O901.5 (3)C1—C9—C20—C22123.2 (3)
C7—C9—C1—C21.6 (4)C7—C9—C20—C2257.9 (3)
C20—C9—C1—C2177.2 (2)C1—C9—C20—C29112.0 (3)
C3—C2—C1—O90178.1 (2)C7—C9—C20—C2966.8 (3)
C10—C2—C1—O900.9 (3)C32—C31—C39—C4188.0 (3)
C3—C2—C1—C92.4 (3)C30—C31—C39—C4189.2 (3)
C10—C2—C1—C9174.9 (2)C32—C31—C39—C4536.0 (3)
C65—C67—C78—C8455.0 (3)C30—C31—C39—C45146.7 (2)
C59—C67—C78—C84129.9 (2)N103—C101—C99—C970.8 (5)
C65—C67—C78—C8068.7 (2)C30—C38—C36—C340.3 (4)
C59—C67—C78—C80106.4 (2)C49—C38—C36—C34178.5 (3)
C61—C60—C68—C7068.5 (3)C101—C99—C97—C950.2 (5)
C59—C60—C68—C70112.1 (3)C93—C95—C97—C991.2 (5)
C61—C60—C68—C7456.7 (3)C2—C3—C5—C71.0 (5)
C59—C60—C68—C74122.7 (3)C9—C7—C5—C31.7 (5)
C3—C2—C10—C1260.2 (4)C31—C32—C34—C360.3 (4)
C1—C2—C10—C12122.6 (3)C38—C36—C34—C320.8 (4)
C3—C2—C10—C1664.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C101—H101···S92i0.932.883.330 (3)111
N103—H103···S920.89 (3)2.13 (3)3.019 (2)172 (3)
Symmetry code: (i) x+1, y+1, z.
(tdst_py_180k) top
Crystal data top
C36H51O3SSi·C5H6NF(000) = 1456
Mr = 672.02Dx = 1.121 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11321 reflections
a = 13.4813 (14) Åθ = 3.0–29.5°
b = 16.3521 (10) ŵ = 0.15 mm1
c = 18.8926 (18) ÅT = 180 K
β = 107.073 (8)°Plate, colorless
V = 3981.3 (6) Å30.38 × 0.31 × 0.15 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
5344 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.049
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.1°
rotation method scansh = 1613
22334 measured reflectionsk = 1920
7795 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0626P)2 + 0.4715P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
7795 reflectionsΔρmax = 0.49 e Å3
440 parametersΔρmin = 0.34 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S920.59552 (4)0.52625 (3)0.09033 (3)0.02984 (13)
Si910.68596 (4)0.51559 (3)0.19646 (3)0.02243 (13)
O900.63001 (10)0.45687 (9)0.24521 (7)0.0255 (3)
O880.70919 (10)0.60025 (9)0.24582 (7)0.0277 (3)
O890.80002 (10)0.47279 (9)0.20391 (7)0.0255 (3)
C600.92779 (15)0.48645 (13)0.14028 (11)0.0278 (4)
N1030.40577 (16)0.43768 (14)0.10528 (11)0.0407 (5)
C650.84637 (17)0.35142 (14)0.05295 (11)0.0323 (5)
H650.81970.30630.02350.039*
C590.84111 (15)0.44544 (13)0.14921 (10)0.0240 (4)
C670.80048 (15)0.37561 (13)0.10712 (10)0.0257 (4)
C90.57325 (18)0.50881 (15)0.34582 (13)0.0376 (5)
C310.86574 (17)0.66577 (15)0.31464 (13)0.0373 (5)
C950.3108 (2)0.33654 (18)0.14290 (17)0.0547 (7)
H950.30830.29160.17250.066*
C630.93019 (17)0.39253 (15)0.04191 (12)0.0360 (5)
H630.9590.37570.00520.043*
C20.70701 (18)0.40185 (15)0.36717 (12)0.0346 (5)
C1010.3216 (2)0.46921 (19)0.05955 (14)0.0512 (7)
H1010.3260.51520.03170.061*
C10.63842 (16)0.45715 (13)0.32060 (11)0.0283 (4)
C800.7644 (2)0.24127 (15)0.15647 (14)0.0415 (6)
H80A0.78960.2110.12180.062*
H80B0.71260.20970.16980.062*
H80C0.82080.25260.20.062*
C780.71648 (16)0.32216 (13)0.12096 (11)0.0289 (4)
H780.68820.35050.15640.035*
C680.97583 (17)0.55878 (14)0.18862 (13)0.0362 (5)
H680.93960.56480.22630.043*
C100.77063 (19)0.34151 (15)0.33829 (13)0.0400 (6)
H100.75770.35260.28540.048*
C610.97049 (17)0.45895 (14)0.08605 (12)0.0336 (5)
H611.02770.4860.07930.04*
C70.5812 (2)0.50460 (19)0.42157 (15)0.0538 (7)
H70.53870.53780.44020.065*
C30.7113 (2)0.40199 (18)0.44186 (13)0.0483 (6)
H30.75690.36660.47410.058*
C320.93213 (19)0.73218 (16)0.32308 (15)0.0469 (6)
H320.99240.73310.36280.056*
C930.40327 (19)0.37290 (17)0.14667 (15)0.0496 (7)
H930.46450.35220.17830.06*
C380.75224 (18)0.73130 (14)0.20324 (13)0.0362 (5)
C300.77625 (16)0.66582 (13)0.25280 (12)0.0292 (5)
C290.3847 (2)0.53916 (19)0.28675 (18)0.0575 (7)
H29A0.37470.48410.26840.086*
H29B0.33760.57490.25260.086*
H29C0.37190.54170.33410.086*
C490.6529 (2)0.73420 (16)0.13838 (14)0.0463 (6)
H490.62040.68010.13460.056*
C200.49605 (18)0.56564 (16)0.29500 (15)0.0428 (6)
H200.50680.56240.2460.051*
C390.8858 (2)0.59768 (17)0.37127 (14)0.0475 (7)
H390.8520.54830.3460.057*
C990.2270 (2)0.4338 (2)0.05317 (15)0.0612 (8)
H990.1670.45530.02050.073*
C360.8219 (2)0.79647 (16)0.21535 (16)0.0486 (6)
H360.80780.84070.1830.058*
C160.7356 (3)0.25384 (19)0.34557 (18)0.0635 (8)
H16A0.74890.24050.3970.095*
H16B0.77330.2170.32340.095*
H16C0.66270.2490.32090.095*
C970.2216 (2)0.3671 (2)0.09497 (16)0.0551 (7)
H970.1580.34260.0910.066*
C50.6502 (2)0.4527 (2)0.46907 (14)0.0585 (8)
H50.65530.45220.51920.07*
C840.62667 (18)0.30550 (16)0.05097 (13)0.0405 (6)
H84A0.59810.35650.0290.061*
H84B0.57390.27450.06370.061*
H84C0.65180.2750.01630.061*
C220.5137 (2)0.65377 (19)0.3207 (2)0.0684 (9)
H22A0.50490.65870.36910.103*
H22B0.46450.68840.28670.103*
H22C0.58280.670.32240.103*
C340.9113 (2)0.79690 (17)0.27426 (17)0.0526 (7)
H340.95720.84070.2810.063*
C510.6723 (3)0.7514 (4)0.0657 (2)0.1182 (19)
H51A0.7020.80490.06690.177*
H51B0.6080.74890.02670.177*
H51C0.71950.71140.0570.177*
C700.9606 (4)0.63715 (19)0.1445 (2)0.0829 (12)
H70A10.63490.10960.124*
H70B0.98380.68260.17740.124*
H70C0.88840.64380.11830.124*
C120.8856 (2)0.3496 (2)0.3745 (3)0.0917 (14)
H12A0.90710.40430.36790.138*
H12B0.92180.31160.35220.138*
H12C0.90110.33790.42640.138*
C410.8371 (3)0.6176 (3)0.43166 (19)0.0747 (10)
H41A0.86820.66630.4570.112*
H41B0.84820.5730.46620.112*
H41C0.76390.62620.41020.112*
C550.5761 (3)0.7956 (3)0.1521 (2)0.1118 (18)
H55A0.56040.78180.1970.168*
H55B0.51350.79440.11140.168*
H55C0.60570.84940.15640.168*
C451.0006 (2)0.5784 (2)0.40480 (17)0.0713 (10)
H45A1.03180.56910.36590.107*
H45B1.00810.53030.4350.107*
H45C1.03440.62360.43460.107*
C741.0892 (2)0.5439 (3)0.2286 (3)0.0963 (15)
H74A1.0960.4950.25780.144*
H74B1.11660.58950.26020.144*
H74C1.12690.53760.1930.144*
H1030.465 (2)0.4622 (18)0.1052 (15)0.053 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S920.0284 (3)0.0332 (3)0.0259 (2)0.0044 (2)0.00488 (19)0.0017 (2)
Si910.0195 (3)0.0246 (3)0.0238 (2)0.0016 (2)0.0073 (2)0.0013 (2)
O900.0238 (7)0.0296 (8)0.0246 (6)0.0015 (6)0.0092 (5)0.0011 (6)
O880.0234 (7)0.0276 (8)0.0317 (7)0.0039 (6)0.0075 (6)0.0065 (6)
O890.0204 (6)0.0325 (8)0.0250 (6)0.0007 (6)0.0087 (5)0.0017 (6)
C600.0224 (10)0.0299 (11)0.0329 (10)0.0017 (8)0.0110 (8)0.0059 (9)
N1030.0355 (11)0.0441 (12)0.0477 (12)0.0080 (10)0.0205 (9)0.0011 (9)
C650.0357 (12)0.0357 (13)0.0266 (10)0.0007 (9)0.0109 (9)0.0033 (9)
C590.0222 (9)0.0273 (11)0.0238 (9)0.0042 (8)0.0087 (7)0.0035 (8)
C670.0249 (10)0.0282 (11)0.0243 (9)0.0018 (8)0.0078 (8)0.0025 (8)
C90.0356 (12)0.0415 (14)0.0423 (12)0.0004 (10)0.0215 (10)0.0023 (10)
C310.0296 (11)0.0365 (13)0.0430 (12)0.0015 (10)0.0064 (9)0.0120 (10)
C950.0466 (15)0.0453 (16)0.0748 (19)0.0030 (12)0.0222 (14)0.0227 (14)
C630.0361 (12)0.0471 (14)0.0315 (11)0.0063 (10)0.0203 (9)0.0023 (10)
C20.0355 (12)0.0406 (13)0.0300 (10)0.0003 (10)0.0131 (9)0.0044 (9)
C1010.0576 (16)0.0599 (18)0.0460 (14)0.0109 (14)0.0306 (12)0.0204 (13)
C10.0261 (10)0.0343 (12)0.0279 (10)0.0021 (9)0.0133 (8)0.0001 (8)
C800.0439 (14)0.0346 (13)0.0508 (14)0.0032 (11)0.0214 (11)0.0053 (11)
C780.0291 (11)0.0281 (11)0.0317 (10)0.0039 (9)0.0124 (9)0.0019 (9)
C680.0306 (11)0.0322 (12)0.0510 (13)0.0061 (9)0.0202 (10)0.0059 (10)
C100.0430 (13)0.0423 (14)0.0361 (12)0.0125 (11)0.0136 (10)0.0102 (10)
C610.0294 (11)0.0400 (13)0.0370 (11)0.0021 (9)0.0182 (9)0.0065 (10)
C70.0597 (17)0.0674 (19)0.0477 (14)0.0053 (14)0.0366 (13)0.0072 (13)
C30.0525 (16)0.0621 (18)0.0308 (12)0.0049 (13)0.0128 (11)0.0091 (11)
C320.0317 (12)0.0427 (15)0.0610 (16)0.0036 (11)0.0055 (11)0.0196 (13)
C930.0330 (13)0.0531 (17)0.0588 (16)0.0021 (11)0.0071 (11)0.0176 (13)
C380.0357 (12)0.0294 (12)0.0441 (13)0.0005 (9)0.0127 (10)0.0048 (10)
C300.0261 (10)0.0268 (11)0.0370 (11)0.0007 (8)0.0125 (9)0.0090 (9)
C290.0383 (14)0.0535 (18)0.082 (2)0.0024 (12)0.0193 (14)0.0025 (15)
C490.0549 (16)0.0300 (13)0.0460 (14)0.0031 (11)0.0026 (12)0.0022 (11)
C200.0347 (13)0.0431 (14)0.0569 (15)0.0075 (11)0.0234 (11)0.0012 (12)
C390.0416 (14)0.0437 (15)0.0440 (14)0.0003 (11)0.0078 (11)0.0047 (11)
C990.0358 (14)0.100 (3)0.0501 (15)0.0187 (15)0.0156 (12)0.0259 (16)
C360.0576 (17)0.0305 (13)0.0603 (16)0.0076 (12)0.0212 (13)0.0023 (12)
C160.082 (2)0.0499 (18)0.0640 (18)0.0020 (16)0.0301 (16)0.0007 (15)
C970.0319 (13)0.070 (2)0.0657 (17)0.0058 (13)0.0183 (12)0.0063 (15)
C50.0706 (19)0.080 (2)0.0314 (12)0.0035 (16)0.0244 (13)0.0008 (13)
C840.0376 (13)0.0410 (14)0.0425 (13)0.0099 (10)0.0110 (10)0.0080 (10)
C220.0482 (17)0.0475 (18)0.110 (3)0.0070 (14)0.0234 (17)0.0050 (17)
C340.0486 (15)0.0372 (15)0.0751 (19)0.0182 (12)0.0228 (14)0.0203 (14)
C510.083 (3)0.212 (6)0.052 (2)0.009 (3)0.0088 (19)0.033 (3)
C700.157 (4)0.0336 (16)0.084 (2)0.009 (2)0.076 (2)0.0046 (16)
C120.0405 (17)0.077 (3)0.151 (4)0.0132 (16)0.019 (2)0.037 (3)
C410.059 (2)0.097 (3)0.069 (2)0.0062 (18)0.0195 (16)0.0230 (19)
C550.058 (2)0.157 (5)0.097 (3)0.037 (3)0.013 (2)0.037 (3)
C450.0548 (19)0.090 (3)0.0576 (18)0.0221 (17)0.0022 (14)0.0033 (17)
C740.0343 (16)0.097 (3)0.139 (3)0.0081 (17)0.0032 (19)0.068 (3)
Geometric parameters (Å, º) top
S92—Si912.0252 (7)C93—H930.93
Si91—O881.6469 (14)C38—C361.394 (3)
Si91—O891.6574 (14)C38—C301.396 (3)
Si91—O901.6575 (14)C38—C491.528 (3)
O90—C11.395 (2)C29—C201.525 (4)
O88—C301.384 (3)C29—H29A0.96
O89—C591.382 (2)C29—H29B0.96
C60—C611.389 (3)C29—H29C0.96
C60—C591.400 (3)C49—C511.498 (5)
C60—C681.518 (3)C49—C551.518 (5)
N103—C1011.313 (3)C49—H490.98
N103—C931.323 (3)C20—C221.517 (4)
N103—H1030.89 (3)C20—H200.98
C65—C631.382 (3)C39—C411.510 (4)
C65—C671.399 (3)C39—C451.524 (4)
C65—H650.93C39—H390.98
C59—C671.407 (3)C99—C971.361 (4)
C67—C781.513 (3)C99—H990.93
C9—C11.399 (3)C36—C341.379 (4)
C9—C71.405 (3)C36—H360.93
C9—C201.511 (3)C16—H16A0.96
C31—C321.386 (4)C16—H16B0.96
C31—C301.412 (3)C16—H16C0.96
C31—C391.512 (4)C97—H970.93
C95—C931.364 (4)C5—H50.93
C95—C971.370 (4)C84—H84A0.96
C95—H950.93C84—H84B0.96
C63—C611.380 (3)C84—H84C0.96
C63—H630.93C22—H22A0.96
C2—C31.395 (3)C22—H22B0.96
C2—C11.403 (3)C22—H22C0.96
C2—C101.510 (3)C34—H340.93
C101—C991.373 (4)C51—H51A0.96
C101—H1010.93C51—H51B0.96
C80—C781.537 (3)C51—H51C0.96
C80—H80A0.96C70—H70A0.96
C80—H80B0.96C70—H70B0.96
C80—H80C0.96C70—H70C0.96
C78—C841.533 (3)C12—H12A0.96
C78—H780.98C12—H12B0.96
C68—C701.510 (4)C12—H12C0.96
C68—C741.512 (4)C41—H41A0.96
C68—H680.98C41—H41B0.96
C10—C121.505 (4)C41—H41C0.96
C10—C161.528 (4)C55—H55A0.96
C10—H100.98C55—H55B0.96
C61—H610.93C55—H55C0.96
C7—C51.378 (4)C45—H45A0.96
C7—H70.93C45—H45B0.96
C3—C51.371 (4)C45—H45C0.96
C3—H30.93C74—H74A0.96
C32—C341.377 (4)C74—H74B0.96
C32—H320.93C74—H74C0.96
O88—Si91—O89106.82 (7)H29B—C29—H29C109.5
O88—Si91—O90102.37 (7)C51—C49—C55110.1 (3)
O89—Si91—O90105.69 (7)C51—C49—C38113.1 (3)
O88—Si91—S92116.57 (6)C55—C49—C38111.4 (2)
O89—Si91—S92113.22 (5)C51—C49—H49107.3
O90—Si91—S92111.10 (5)C55—C49—H49107.3
C1—O90—Si91130.65 (13)C38—C49—H49107.3
C30—O88—Si91135.70 (13)C9—C20—C22111.5 (2)
C59—O89—Si91129.68 (12)C9—C20—C29111.3 (2)
C61—C60—C59118.4 (2)C22—C20—C29111.1 (2)
C61—C60—C68119.99 (19)C9—C20—H20107.6
C59—C60—C68121.64 (19)C22—C20—H20107.6
C101—N103—C93122.4 (2)C29—C20—H20107.6
C101—N103—H103114.9 (18)C41—C39—C31110.4 (2)
C93—N103—H103122.7 (19)C41—C39—C45110.2 (2)
C63—C65—C67122.0 (2)C31—C39—C45113.3 (3)
C63—C65—H65119C41—C39—H39107.6
C67—C65—H65119C31—C39—H39107.6
O89—C59—C60117.84 (18)C45—C39—H39107.6
O89—C59—C67120.67 (17)C97—C99—C101119.5 (2)
C60—C59—C67121.39 (18)C97—C99—H99120.2
C65—C67—C59117.41 (19)C101—C99—H99120.2
C65—C67—C78118.51 (19)C34—C36—C38121.5 (3)
C59—C67—C78123.91 (18)C34—C36—H36119.2
C1—C9—C7116.7 (2)C38—C36—H36119.2
C1—C9—C20122.6 (2)C10—C16—H16A109.5
C7—C9—C20120.7 (2)C10—C16—H16B109.5
C32—C31—C30117.4 (2)H16A—C16—H16B109.5
C32—C31—C39121.3 (2)C10—C16—H16C109.5
C30—C31—C39121.2 (2)H16A—C16—H16C109.5
C93—C95—C97119.1 (3)H16B—C16—H16C109.5
C93—C95—H95120.4C99—C97—C95119.4 (3)
C97—C95—H95120.4C99—C97—H97120.3
C61—C63—C65119.1 (2)C95—C97—H97120.3
C61—C63—H63120.5C3—C5—C7119.5 (2)
C65—C63—H63120.5C3—C5—H5120.2
C3—C2—C1117.2 (2)C7—C5—H5120.2
C3—C2—C10120.5 (2)C78—C84—H84A109.5
C1—C2—C10122.28 (19)C78—C84—H84B109.5
N103—C101—C99119.6 (3)H84A—C84—H84B109.5
N103—C101—H101120.2C78—C84—H84C109.5
C99—C101—H101120.2H84A—C84—H84C109.5
O90—C1—C9118.59 (19)H84B—C84—H84C109.5
O90—C1—C2118.62 (19)C20—C22—H22A109.5
C9—C1—C2122.7 (2)C20—C22—H22B109.5
C78—C80—H80A109.5H22A—C22—H22B109.5
C78—C80—H80B109.5C20—C22—H22C109.5
H80A—C80—H80B109.5H22A—C22—H22C109.5
C78—C80—H80C109.5H22B—C22—H22C109.5
H80A—C80—H80C109.5C32—C34—C36119.7 (2)
H80B—C80—H80C109.5C32—C34—H34120.2
C67—C78—C84113.28 (18)C36—C34—H34120.2
C67—C78—C80109.44 (18)C49—C51—H51A109.5
C84—C78—C80110.35 (19)C49—C51—H51B109.5
C67—C78—H78107.9H51A—C51—H51B109.5
C84—C78—H78107.9C49—C51—H51C109.5
C80—C78—H78107.9H51A—C51—H51C109.5
C70—C68—C74111.5 (3)H51B—C51—H51C109.5
C70—C68—C60111.4 (2)C68—C70—H70A109.5
C74—C68—C60111.4 (2)C68—C70—H70B109.5
C70—C68—H68107.5H70A—C70—H70B109.5
C74—C68—H68107.5C68—C70—H70C109.5
C60—C68—H68107.5H70A—C70—H70C109.5
C12—C10—C2113.4 (2)H70B—C70—H70C109.5
C12—C10—C16110.2 (3)C10—C12—H12A109.5
C2—C10—C16110.9 (2)C10—C12—H12B109.5
C12—C10—H10107.3H12A—C12—H12B109.5
C2—C10—H10107.3C10—C12—H12C109.5
C16—C10—H10107.3H12A—C12—H12C109.5
C63—C61—C60121.7 (2)H12B—C12—H12C109.5
C63—C61—H61119.1C39—C41—H41A109.5
C60—C61—H61119.1C39—C41—H41B109.5
C5—C7—C9121.9 (3)H41A—C41—H41B109.5
C5—C7—H7119C39—C41—H41C109.5
C9—C7—H7119H41A—C41—H41C109.5
C5—C3—C2122.0 (2)H41B—C41—H41C109.5
C5—C3—H3119C49—C55—H55A109.5
C2—C3—H3119C49—C55—H55B109.5
C34—C32—C31121.8 (2)H55A—C55—H55B109.5
C34—C32—H32119.1C49—C55—H55C109.5
C31—C32—H32119.1H55A—C55—H55C109.5
N103—C93—C95120.0 (2)H55B—C55—H55C109.5
N103—C93—H93120C39—C45—H45A109.5
C95—C93—H93120C39—C45—H45B109.5
C36—C38—C30117.6 (2)H45A—C45—H45B109.5
C36—C38—C49119.8 (2)C39—C45—H45C109.5
C30—C38—C49122.5 (2)H45A—C45—H45C109.5
O88—C30—C38120.93 (18)H45B—C45—H45C109.5
O88—C30—C31117.0 (2)C68—C74—H74A109.5
C38—C30—C31121.9 (2)C68—C74—H74B109.5
C20—C29—H29A109.5H74A—C74—H74B109.5
C20—C29—H29B109.5C68—C74—H74C109.5
H29A—C29—H29B109.5H74A—C74—H74C109.5
C20—C29—H29C109.5H74B—C74—H74C109.5
H29A—C29—H29C109.5
O88—Si91—O90—C126.14 (18)C1—C2—C10—C16112.8 (3)
O89—Si91—O90—C185.54 (17)C65—C63—C61—C601.2 (3)
S92—Si91—O90—C1151.27 (15)C59—C60—C61—C630.6 (3)
O89—Si91—O88—C3047.5 (2)C68—C60—C61—C63178.8 (2)
O90—Si91—O88—C30158.30 (18)C1—C9—C7—C50.5 (4)
S92—Si91—O88—C3080.25 (19)C20—C9—C7—C5179.3 (3)
O88—Si91—O89—C59128.56 (16)C1—C2—C3—C51.1 (4)
O90—Si91—O89—C59122.94 (16)C10—C2—C3—C5176.2 (3)
S92—Si91—O89—C591.11 (18)C30—C31—C32—C341.4 (4)
Si91—O89—C59—C60113.90 (18)C39—C31—C32—C34176.0 (3)
Si91—O89—C59—C6769.8 (2)C101—N103—C93—C950.2 (4)
C61—C60—C59—O89179.29 (17)C97—C95—C93—N1031.2 (5)
C68—C60—C59—O890.1 (3)Si91—O88—C30—C3883.2 (3)
C61—C60—C59—C673.0 (3)Si91—O88—C30—C31100.9 (2)
C68—C60—C59—C67176.35 (19)C36—C38—C30—O88177.8 (2)
C63—C65—C67—C591.7 (3)C49—C38—C30—O881.0 (3)
C63—C65—C67—C78173.7 (2)C36—C38—C30—C312.1 (3)
O89—C59—C67—C65179.73 (17)C49—C38—C30—C31176.7 (2)
C60—C59—C67—C653.6 (3)C32—C31—C30—O88178.5 (2)
O89—C59—C67—C784.6 (3)C39—C31—C30—O881.1 (3)
C60—C59—C67—C78171.57 (19)C32—C31—C30—C382.6 (3)
C67—C65—C63—C610.6 (3)C39—C31—C30—C38174.8 (2)
C93—N103—C101—C990.8 (4)C36—C38—C49—C5153.1 (4)
Si91—O90—C1—C986.7 (2)C30—C38—C49—C51128.1 (3)
Si91—O90—C1—C297.4 (2)C36—C38—C49—C5571.6 (4)
C7—C9—C1—O90177.4 (2)C30—C38—C49—C55107.2 (3)
C20—C9—C1—O901.5 (3)C1—C9—C20—C22123.2 (3)
C7—C9—C1—C21.6 (4)C7—C9—C20—C2258.0 (3)
C20—C9—C1—C2177.2 (2)C1—C9—C20—C29112.1 (3)
C3—C2—C1—O90178.1 (2)C7—C9—C20—C2966.7 (3)
C10—C2—C1—O900.9 (3)C32—C31—C39—C4188.0 (3)
C3—C2—C1—C92.4 (3)C30—C31—C39—C4189.2 (3)
C10—C2—C1—C9174.9 (2)C32—C31—C39—C4536.1 (3)
C65—C67—C78—C8455.0 (3)C30—C31—C39—C45146.7 (2)
C59—C67—C78—C84129.9 (2)N103—C101—C99—C970.8 (5)
C65—C67—C78—C8068.6 (2)C30—C38—C36—C340.3 (4)
C59—C67—C78—C80106.5 (2)C49—C38—C36—C34178.5 (3)
C61—C60—C68—C7068.4 (3)C101—C99—C97—C950.2 (5)
C59—C60—C68—C70112.2 (3)C93—C95—C97—C991.1 (5)
C61—C60—C68—C7456.7 (3)C2—C3—C5—C70.9 (5)
C59—C60—C68—C74122.7 (3)C9—C7—C5—C31.7 (5)
C3—C2—C10—C1260.3 (4)C31—C32—C34—C360.3 (4)
C1—C2—C10—C12122.5 (3)C38—C36—C34—C320.8 (4)
C3—C2—C10—C1664.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C101—H101···S92i0.932.893.336 (3)111
N103—H103···S920.89 (3)2.14 (3)3.024 (2)172 (3)
Symmetry code: (i) x+1, y+1, z.
(tdst_py_210) top
Crystal data top
C36H51O3SSi·C5H6NF(000) = 1456
Mr = 672.02Dx = 1.114 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11992 reflections
a = 13.5052 (13) Åθ = 3–29.4°
b = 16.382 (1) ŵ = 0.15 mm1
c = 18.9409 (18) ÅT = 210 K
β = 107.106 (7)°Plate, colorless
V = 4005.1 (6) Å30.38 × 0.31 × 0.15 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
4399 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.066
Detector resolution: 6.67 pixels mm-1θmax = 26°, θmin = 3.1°
rotation method scansh = 1316
22528 measured reflectionsk = 2020
7841 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0591P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
7841 reflectionsΔρmax = 0.31 e Å3
440 parametersΔρmin = 0.31 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S920.59524 (5)0.52640 (5)0.09064 (3)0.03577 (18)
Si910.68620 (5)0.51613 (5)0.19644 (4)0.02701 (17)
O900.63079 (13)0.45791 (11)0.24549 (8)0.0301 (4)
O880.70985 (13)0.60078 (11)0.24550 (9)0.0327 (4)
O890.79972 (12)0.47322 (11)0.20388 (8)0.0297 (4)
C600.92693 (19)0.48708 (17)0.14009 (13)0.0315 (6)
N1030.4057 (2)0.43769 (18)0.10531 (15)0.0484 (7)
C650.8459 (2)0.35176 (19)0.05341 (14)0.0387 (7)
H650.81960.30640.02450.046*
C590.84067 (19)0.44578 (16)0.14901 (13)0.0274 (5)
C670.8002 (2)0.37621 (16)0.10702 (13)0.0311 (6)
C90.5740 (2)0.5096 (2)0.34572 (16)0.0447 (7)
C310.8657 (2)0.66625 (19)0.31437 (16)0.0431 (7)
C950.3109 (3)0.3379 (2)0.1437 (2)0.0640 (10)
H950.30840.29350.17370.077*
C630.9290 (2)0.3927 (2)0.04195 (15)0.0434 (7)
H630.95750.37580.00530.052*
C20.7070 (2)0.40291 (19)0.36708 (14)0.0408 (7)
C1010.3216 (3)0.4686 (2)0.05961 (17)0.0588 (9)
H1010.32590.5140.03110.071*
C10.6391 (2)0.45814 (17)0.32071 (13)0.0334 (6)
C800.7640 (3)0.24220 (19)0.15656 (18)0.0496 (8)
H80A0.78890.21170.1220.074*
H80B0.71250.21090.17030.074*
H80C0.82060.25370.19980.074*
C780.7163 (2)0.32239 (17)0.12103 (14)0.0343 (6)
H780.68790.35070.15630.041*
C680.9749 (2)0.55907 (18)0.18758 (17)0.0428 (7)
H680.93810.56570.22470.051*
C100.7704 (2)0.3426 (2)0.33887 (16)0.0468 (8)
H100.75750.35360.28610.056*
C610.9692 (2)0.45900 (19)0.08557 (15)0.0398 (7)
H611.02630.48590.07860.048*
C70.5822 (3)0.5057 (3)0.42166 (19)0.0652 (10)
H70.540.53880.44040.078*
C30.7114 (3)0.4034 (2)0.44184 (16)0.0581 (9)
H30.7570.36820.47420.07*
C320.9321 (2)0.7325 (2)0.3228 (2)0.0546 (9)
H320.9920.73350.36270.066*
C930.4033 (3)0.3737 (2)0.14691 (19)0.0593 (9)
H930.46460.35310.17840.071*
C380.7536 (2)0.73133 (19)0.20259 (16)0.0443 (7)
C300.7773 (2)0.66615 (17)0.25278 (14)0.0333 (6)
C290.3853 (3)0.5403 (2)0.2867 (2)0.0682 (10)
H29A0.37560.48460.27030.102*
H29B0.33860.57470.2510.102*
H29C0.37140.54520.33340.102*
C490.6545 (3)0.7344 (2)0.13784 (17)0.0558 (9)
H490.62280.68010.13360.067*
C200.4966 (2)0.5661 (2)0.29514 (19)0.0502 (8)
H200.50710.56260.24620.06*
C390.8854 (3)0.5987 (2)0.37133 (17)0.0556 (9)
H390.85080.54950.34650.067*
C990.2276 (3)0.4340 (3)0.05409 (19)0.0701 (12)
H990.16760.45560.02180.084*
C360.8230 (3)0.7963 (2)0.2155 (2)0.0571 (9)
H360.80880.84080.18370.069*
C160.7348 (4)0.2552 (2)0.3457 (2)0.0755 (11)
H16A0.74660.24210.39690.113*
H16B0.77320.21830.32440.113*
H16C0.66230.25050.320.113*
C970.2225 (3)0.3678 (3)0.0960 (2)0.0657 (10)
H970.15910.34320.09210.079*
C50.6511 (3)0.4540 (3)0.46846 (19)0.0720 (12)
H50.65650.45360.51860.086*
C840.6272 (2)0.3059 (2)0.05143 (17)0.0486 (8)
H84A0.59890.35680.02940.073*
H84B0.57430.27520.06410.073*
H84C0.65230.27530.0170.073*
C220.5136 (3)0.6547 (2)0.3200 (3)0.0788 (12)
H22A0.50340.66030.36780.118*
H22B0.46510.68880.28520.118*
H22C0.58290.67070.32260.118*
C340.9118 (3)0.7964 (2)0.2740 (2)0.0610 (10)
H340.95810.83980.28050.073*
C510.6746 (4)0.7523 (5)0.0654 (2)0.135 (3)
H51A0.70310.80610.06670.203*
H51B0.61070.74910.02610.203*
H51C0.72270.7130.0570.203*
C700.9608 (5)0.6370 (2)0.1435 (2)0.0958 (16)
H70A1.00290.63540.11060.144*
H70B0.98110.68260.17640.144*
H70C0.88930.64270.11530.144*
C120.8856 (3)0.3500 (3)0.3745 (3)0.1072 (18)
H12A0.90770.40420.36690.161*
H12B0.9210.31110.35270.161*
H12C0.90140.33950.42650.161*
C410.8379 (3)0.6192 (3)0.4322 (2)0.0891 (14)
H41A0.86980.66760.45750.134*
H41B0.84870.57460.46650.134*
H41C0.76490.62840.41120.134*
C550.5762 (4)0.7946 (4)0.1516 (3)0.129 (2)
H55A0.56080.78030.19640.193*
H55B0.51370.79280.1110.193*
H55C0.60460.84880.1560.193*
C450.9992 (3)0.5784 (3)0.4045 (2)0.0854 (14)
H45A1.02980.56830.36550.128*
H45B1.00590.53050.43480.128*
H45C1.03380.62330.4340.128*
C741.0883 (3)0.5433 (3)0.2289 (3)0.111 (2)
H74A1.09360.49570.25940.166*
H74B1.11630.58960.25930.166*
H74C1.12650.53460.19410.166*
H1030.463 (3)0.462 (2)0.1070 (19)0.068 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S920.0345 (4)0.0397 (4)0.0301 (3)0.0049 (3)0.0049 (3)0.0022 (3)
Si910.0238 (3)0.0292 (4)0.0284 (3)0.0024 (3)0.0083 (3)0.0013 (3)
O900.0280 (9)0.0350 (11)0.0296 (8)0.0014 (8)0.0121 (7)0.0008 (7)
O880.0305 (10)0.0321 (11)0.0352 (9)0.0045 (8)0.0090 (7)0.0064 (8)
O890.0234 (8)0.0391 (11)0.0280 (8)0.0024 (8)0.0098 (6)0.0033 (8)
C600.0272 (13)0.0339 (15)0.0350 (13)0.0006 (11)0.0116 (10)0.0035 (11)
N1030.0425 (16)0.0503 (17)0.0577 (16)0.0083 (14)0.0229 (13)0.0003 (13)
C650.0442 (17)0.0407 (18)0.0327 (13)0.0013 (13)0.0136 (12)0.0035 (12)
C590.0252 (12)0.0303 (14)0.0274 (11)0.0033 (10)0.0088 (10)0.0039 (10)
C670.0304 (14)0.0327 (15)0.0301 (12)0.0009 (11)0.0088 (10)0.0017 (11)
C90.0436 (16)0.050 (2)0.0480 (16)0.0042 (14)0.0242 (13)0.0009 (14)
C310.0349 (15)0.0390 (18)0.0507 (16)0.0001 (13)0.0055 (13)0.0147 (14)
C950.055 (2)0.054 (2)0.086 (3)0.0008 (17)0.0250 (19)0.027 (2)
C630.0484 (17)0.0496 (19)0.0388 (15)0.0060 (15)0.0231 (13)0.0003 (14)
C20.0412 (16)0.0481 (19)0.0346 (14)0.0025 (14)0.0136 (12)0.0074 (13)
C1010.068 (2)0.066 (2)0.0533 (18)0.013 (2)0.0351 (17)0.0238 (18)
C10.0335 (14)0.0379 (17)0.0336 (13)0.0034 (12)0.0173 (11)0.0010 (12)
C800.056 (2)0.0379 (18)0.0607 (19)0.0035 (15)0.0257 (15)0.0043 (15)
C780.0362 (15)0.0330 (16)0.0354 (14)0.0031 (12)0.0130 (11)0.0041 (12)
C680.0375 (16)0.0379 (17)0.0590 (17)0.0057 (13)0.0235 (14)0.0034 (14)
C100.0518 (18)0.048 (2)0.0412 (15)0.0150 (15)0.0137 (13)0.0125 (14)
C610.0360 (15)0.0467 (19)0.0428 (15)0.0007 (13)0.0210 (12)0.0077 (13)
C70.074 (2)0.080 (3)0.057 (2)0.004 (2)0.0427 (18)0.0133 (19)
C30.064 (2)0.076 (3)0.0368 (16)0.0079 (19)0.0187 (15)0.0111 (16)
C320.0370 (17)0.050 (2)0.070 (2)0.0043 (15)0.0056 (15)0.0230 (18)
C930.0410 (19)0.062 (2)0.069 (2)0.0039 (16)0.0059 (16)0.0187 (18)
C380.0486 (18)0.0331 (18)0.0504 (17)0.0022 (14)0.0135 (14)0.0071 (14)
C300.0303 (14)0.0301 (15)0.0407 (14)0.0005 (11)0.0122 (11)0.0110 (12)
C290.0447 (19)0.068 (3)0.094 (3)0.0049 (18)0.0227 (18)0.002 (2)
C490.070 (2)0.0347 (18)0.0513 (18)0.0032 (16)0.0007 (16)0.0045 (15)
C200.0417 (17)0.051 (2)0.067 (2)0.0078 (15)0.0300 (15)0.0019 (16)
C390.048 (2)0.054 (2)0.0507 (18)0.0006 (16)0.0073 (15)0.0058 (16)
C990.043 (2)0.112 (3)0.057 (2)0.019 (2)0.0176 (16)0.033 (2)
C360.067 (2)0.0332 (19)0.072 (2)0.0102 (16)0.0221 (19)0.0042 (16)
C160.095 (3)0.058 (3)0.080 (3)0.001 (2)0.037 (2)0.001 (2)
C970.0373 (18)0.083 (3)0.080 (2)0.0064 (18)0.0221 (17)0.011 (2)
C50.086 (3)0.098 (3)0.0397 (17)0.001 (2)0.0306 (18)0.002 (2)
C840.0420 (18)0.049 (2)0.0521 (18)0.0120 (14)0.0104 (14)0.0110 (15)
C220.057 (2)0.058 (3)0.120 (3)0.0098 (19)0.024 (2)0.003 (2)
C340.050 (2)0.048 (2)0.088 (3)0.0214 (17)0.0250 (19)0.023 (2)
C510.097 (4)0.238 (8)0.065 (3)0.008 (4)0.016 (3)0.039 (4)
C700.180 (5)0.040 (2)0.095 (3)0.012 (3)0.084 (3)0.007 (2)
C120.053 (3)0.092 (4)0.168 (5)0.012 (2)0.020 (3)0.041 (3)
C410.074 (3)0.116 (4)0.080 (3)0.007 (3)0.028 (2)0.025 (3)
C550.067 (3)0.184 (6)0.109 (4)0.050 (4)0.015 (3)0.040 (4)
C450.071 (3)0.100 (4)0.069 (2)0.026 (2)0.005 (2)0.006 (2)
C740.044 (2)0.109 (4)0.158 (5)0.006 (2)0.004 (3)0.077 (4)
Geometric parameters (Å, º) top
S92—Si912.0261 (9)C93—H930.93
Si91—O881.6473 (18)C38—C361.391 (4)
Si91—O891.6545 (18)C38—C301.403 (4)
Si91—O901.6558 (18)C38—C491.527 (4)
O90—C11.396 (3)C29—C201.524 (5)
O88—C301.387 (3)C29—H29A0.96
O89—C591.388 (3)C29—H29B0.96
C60—C611.397 (4)C29—H29C0.96
C60—C591.400 (3)C49—C511.504 (6)
C60—C681.509 (4)C49—C551.524 (6)
N103—C1011.311 (4)C49—H490.98
N103—C931.317 (4)C20—C221.522 (5)
N103—H1030.86 (4)C20—H200.98
C65—C631.379 (4)C39—C411.513 (5)
C65—C671.393 (4)C39—C451.516 (5)
C65—H650.93C39—H390.98
C59—C671.405 (4)C99—C971.357 (5)
C67—C781.520 (4)C99—H990.93
C9—C11.398 (4)C36—C341.374 (5)
C9—C71.411 (4)C36—H360.93
C9—C201.509 (4)C16—H16A0.96
C31—C321.387 (4)C16—H16B0.96
C31—C301.402 (4)C16—H16C0.96
C31—C391.513 (5)C97—H970.93
C95—C971.359 (5)C5—H50.93
C95—C931.365 (5)C84—H84A0.96
C95—H950.93C84—H84B0.96
C63—C611.376 (4)C84—H84C0.96
C63—H630.93C22—H22A0.96
C2—C11.399 (4)C22—H22B0.96
C2—C31.399 (4)C22—H22C0.96
C2—C101.505 (4)C34—H340.93
C101—C991.366 (5)C51—H51A0.96
C101—H1010.93C51—H51B0.96
C80—C781.529 (4)C51—H51C0.96
C80—H80A0.96C70—H70A0.96
C80—H80B0.96C70—H70B0.96
C80—H80C0.96C70—H70C0.96
C78—C841.525 (4)C12—H12A0.96
C78—H780.98C12—H12B0.96
C68—C701.507 (5)C12—H12C0.96
C68—C741.523 (5)C41—H41A0.96
C68—H680.98C41—H41B0.96
C10—C121.507 (5)C41—H41C0.96
C10—C161.527 (5)C55—H55A0.96
C10—H100.98C55—H55B0.96
C61—H610.93C55—H55C0.96
C7—C51.372 (5)C45—H45A0.96
C7—H70.93C45—H45B0.96
C3—C51.359 (5)C45—H45C0.96
C3—H30.93C74—H74A0.96
C32—C341.370 (5)C74—H74B0.96
C32—H320.93C74—H74C0.96
O88—Si91—O89106.77 (9)H29B—C29—H29C109.5
O88—Si91—O90102.30 (9)C51—C49—C55110.5 (4)
O89—Si91—O90105.54 (9)C51—C49—C38112.8 (4)
O88—Si91—S92116.65 (8)C55—C49—C38111.9 (3)
O89—Si91—S92113.36 (7)C51—C49—H49107.1
O90—Si91—S92111.11 (7)C55—C49—H49107.1
C1—O90—Si91131.10 (16)C38—C49—H49107.1
C30—O88—Si91135.97 (16)C9—C20—C22112.0 (3)
C59—O89—Si91129.59 (15)C9—C20—C29112.0 (3)
C61—C60—C59117.8 (2)C22—C20—C29110.6 (3)
C61—C60—C68120.0 (2)C9—C20—H20107.3
C59—C60—C68122.2 (2)C22—C20—H20107.3
C101—N103—C93122.3 (3)C29—C20—H20107.3
C101—N103—H103116 (2)C41—C39—C31110.9 (3)
C93—N103—H103122 (3)C41—C39—C45109.8 (3)
C63—C65—C67122.0 (3)C31—C39—C45113.6 (3)
C63—C65—H65119C41—C39—H39107.4
C67—C65—H65119C31—C39—H39107.4
O89—C59—C60117.6 (2)C45—C39—H39107.4
O89—C59—C67120.8 (2)C97—C99—C101119.6 (3)
C60—C59—C67121.5 (2)C97—C99—H99120.2
C65—C67—C59117.6 (2)C101—C99—H99120.2
C65—C67—C78118.3 (2)C34—C36—C38121.8 (3)
C59—C67—C78123.9 (2)C34—C36—H36119.1
C1—C9—C7116.7 (3)C38—C36—H36119.1
C1—C9—C20122.8 (3)C10—C16—H16A109.5
C7—C9—C20120.5 (3)C10—C16—H16B109.5
C32—C31—C30117.4 (3)H16A—C16—H16B109.5
C32—C31—C39121.2 (3)C10—C16—H16C109.5
C30—C31—C39121.4 (3)H16A—C16—H16C109.5
C97—C95—C93119.2 (3)H16B—C16—H16C109.5
C97—C95—H95120.4C99—C97—C95119.4 (3)
C93—C95—H95120.4C99—C97—H97120.3
C61—C63—C65119.0 (3)C95—C97—H97120.3
C61—C63—H63120.5C3—C5—C7120.2 (3)
C65—C63—H63120.5C3—C5—H5119.9
C1—C2—C3117.2 (3)C7—C5—H5119.9
C1—C2—C10122.6 (2)C78—C84—H84A109.5
C3—C2—C10120.2 (3)C78—C84—H84B109.5
N103—C101—C99119.7 (3)H84A—C84—H84B109.5
N103—C101—H101120.2C78—C84—H84C109.5
C99—C101—H101120.2H84A—C84—H84C109.5
O90—C1—C9118.5 (2)H84B—C84—H84C109.5
O90—C1—C2118.7 (2)C20—C22—H22A109.5
C9—C1—C2122.6 (2)C20—C22—H22B109.5
C78—C80—H80A109.5H22A—C22—H22B109.5
C78—C80—H80B109.5C20—C22—H22C109.5
H80A—C80—H80B109.5H22A—C22—H22C109.5
C78—C80—H80C109.5H22B—C22—H22C109.5
H80A—C80—H80C109.5C32—C34—C36119.8 (3)
H80B—C80—H80C109.5C32—C34—H34120.1
C67—C78—C84113.0 (2)C36—C34—H34120.1
C67—C78—C80109.6 (2)C49—C51—H51A109.5
C84—C78—C80110.6 (3)C49—C51—H51B109.5
C67—C78—H78107.8H51A—C51—H51B109.5
C84—C78—H78107.8C49—C51—H51C109.5
C80—C78—H78107.8H51A—C51—H51C109.5
C70—C68—C60111.7 (3)H51B—C51—H51C109.5
C70—C68—C74111.9 (4)C68—C70—H70A109.5
C60—C68—C74111.4 (3)C68—C70—H70B109.5
C70—C68—H68107.2H70A—C70—H70B109.5
C60—C68—H68107.2C68—C70—H70C109.5
C74—C68—H68107.2H70A—C70—H70C109.5
C2—C10—C12114.1 (3)H70B—C70—H70C109.5
C2—C10—C16111.0 (3)C10—C12—H12A109.5
C12—C10—C16110.3 (3)C10—C12—H12B109.5
C2—C10—H10107H12A—C12—H12B109.5
C12—C10—H10107C10—C12—H12C109.5
C16—C10—H10107H12A—C12—H12C109.5
C63—C61—C60121.9 (3)H12B—C12—H12C109.5
C63—C61—H61119C39—C41—H41A109.5
C60—C61—H61119C39—C41—H41B109.5
C5—C7—C9121.5 (3)H41A—C41—H41B109.5
C5—C7—H7119.3C39—C41—H41C109.5
C9—C7—H7119.3H41A—C41—H41C109.5
C5—C3—C2121.8 (3)H41B—C41—H41C109.5
C5—C3—H3119.1C49—C55—H55A109.5
C2—C3—H3119.1C49—C55—H55B109.5
C34—C32—C31121.7 (3)H55A—C55—H55B109.5
C34—C32—H32119.1C49—C55—H55C109.5
C31—C32—H32119.1H55A—C55—H55C109.5
N103—C93—C95119.9 (3)H55B—C55—H55C109.5
N103—C93—H93120.1C39—C45—H45A109.5
C95—C93—H93120.1C39—C45—H45B109.5
C36—C38—C30117.1 (3)H45A—C45—H45B109.5
C36—C38—C49120.2 (3)C39—C45—H45C109.5
C30—C38—C49122.7 (3)H45A—C45—H45C109.5
O88—C30—C31117.2 (3)H45B—C45—H45C109.5
O88—C30—C38120.5 (2)C68—C74—H74A109.5
C31—C30—C38122.1 (3)C68—C74—H74B109.5
C20—C29—H29A109.5H74A—C74—H74B109.5
C20—C29—H29B109.5C68—C74—H74C109.5
H29A—C29—H29B109.5H74A—C74—H74C109.5
C20—C29—H29C109.5H74B—C74—H74C109.5
H29A—C29—H29C109.5
O88—Si91—O90—C126.0 (2)C3—C2—C10—C1665.1 (4)
O89—Si91—O90—C185.6 (2)C65—C63—C61—C601.4 (4)
S92—Si91—O90—C1151.15 (19)C59—C60—C61—C630.5 (4)
O89—Si91—O88—C3047.1 (3)C68—C60—C61—C63178.8 (3)
O90—Si91—O88—C30157.7 (2)C1—C9—C7—C50.3 (5)
S92—Si91—O88—C3080.9 (2)C20—C9—C7—C5179.2 (3)
O88—Si91—O89—C59128.3 (2)C1—C2—C3—C51.4 (5)
O90—Si91—O89—C59123.4 (2)C10—C2—C3—C5176.4 (4)
S92—Si91—O89—C591.5 (2)C30—C31—C32—C341.3 (5)
Si91—O89—C59—C60113.5 (2)C39—C31—C32—C34175.9 (3)
Si91—O89—C59—C6770.0 (3)C101—N103—C93—C950.5 (6)
C61—C60—C59—O89179.2 (2)C97—C95—C93—N1031.5 (6)
C68—C60—C59—O890.1 (4)Si91—O88—C30—C31101.0 (3)
C61—C60—C59—C672.7 (4)Si91—O88—C30—C3882.8 (3)
C68—C60—C59—C67176.6 (2)C32—C31—C30—O88178.5 (2)
C63—C65—C67—C591.1 (4)C39—C31—C30—O881.3 (4)
C63—C65—C67—C78173.8 (3)C32—C31—C30—C382.4 (4)
O89—C59—C67—C65179.4 (2)C39—C31—C30—C38174.8 (3)
C60—C59—C67—C653.0 (4)C36—C38—C30—O88177.2 (3)
O89—C59—C67—C784.8 (4)C49—C38—C30—O880.3 (4)
C60—C59—C67—C78171.6 (2)C36—C38—C30—C311.3 (4)
C67—C65—C63—C611.1 (4)C49—C38—C30—C31176.3 (3)
C93—N103—C101—C990.2 (5)C36—C38—C49—C5153.3 (5)
Si91—O90—C1—C986.7 (3)C30—C38—C49—C51129.2 (4)
Si91—O90—C1—C297.7 (3)C36—C38—C49—C5572.1 (5)
C7—C9—C1—O90177.7 (3)C30—C38—C49—C55105.4 (4)
C20—C9—C1—O901.2 (4)C1—C9—C20—C22123.0 (4)
C7—C9—C1—C22.2 (5)C7—C9—C20—C2258.2 (4)
C20—C9—C1—C2176.7 (3)C1—C9—C20—C29112.1 (3)
C3—C2—C1—O90178.5 (3)C7—C9—C20—C2966.7 (4)
C10—C2—C1—O900.8 (4)C32—C31—C39—C4187.1 (4)
C3—C2—C1—C93.0 (5)C30—C31—C39—C4190.0 (4)
C10—C2—C1—C9174.7 (3)C32—C31—C39—C4537.1 (4)
C65—C67—C78—C8455.4 (3)C30—C31—C39—C45145.7 (3)
C59—C67—C78—C84130.0 (3)N103—C101—C99—C970.1 (6)
C65—C67—C78—C8068.4 (3)C30—C38—C36—C341.0 (5)
C59—C67—C78—C80106.1 (3)C49—C38—C36—C34178.7 (3)
C61—C60—C68—C7067.9 (4)C101—C99—C97—C951.0 (6)
C59—C60—C68—C70112.8 (3)C93—C95—C97—C991.7 (6)
C61—C60—C68—C7458.1 (4)C2—C3—C5—C70.9 (6)
C59—C60—C68—C74121.2 (4)C9—C7—C5—C31.8 (6)
C1—C2—C10—C12122.1 (4)C31—C32—C34—C360.9 (5)
C3—C2—C10—C1260.3 (5)C38—C36—C34—C322.1 (6)
C1—C2—C10—C16112.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N103—H103···S920.86 (4)2.18 (4)3.026 (3)170 (3)
(tdst_py_240) top
Crystal data top
C36H51O3SSi·C5H6NF(000) = 1456
Mr = 672.02Dx = 1.11 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10921 reflections
a = 13.5221 (18) Åθ = 1.6–29.3°
b = 16.3924 (13) ŵ = 0.15 mm1
c = 18.982 (2) ÅT = 240 K
β = 107.079 (10)°Plate, colorless
V = 4022.0 (8) Å30.38 × 0.31 × 0.15 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
4513 reflections with I > 2σ(I)
Parabolic x-ray mirror monochromatorRint = 0.063
Detector resolution: 6.67 pixels mm-1θmax = 26°, θmin = 3.1°
rotation method scansh = 1216
22221 measured reflectionsk = 1920
7876 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.0653P)2 + 0.1544P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
7876 reflectionsΔρmax = 0.33 e Å3
440 parametersΔρmin = 0.28 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S920.59510 (5)0.52651 (5)0.09091 (3)0.04049 (18)
Si910.68647 (5)0.51657 (5)0.19639 (3)0.03007 (17)
O900.63149 (13)0.45864 (11)0.24571 (9)0.0345 (4)
O880.71034 (13)0.60122 (11)0.24506 (9)0.0363 (4)
O890.79959 (12)0.47364 (11)0.20351 (8)0.0336 (4)
C600.92631 (19)0.48725 (17)0.13961 (13)0.0354 (6)
N1030.4062 (2)0.43817 (18)0.10533 (15)0.0556 (7)
C650.8459 (2)0.35254 (19)0.05347 (14)0.0438 (7)
H650.81930.30750.02420.053*
C590.84062 (18)0.44613 (16)0.14882 (13)0.0320 (6)
C670.79984 (19)0.37644 (16)0.10716 (13)0.0336 (6)
C90.5747 (2)0.5101 (2)0.34565 (16)0.0502 (7)
C310.8658 (2)0.66671 (19)0.31436 (17)0.0472 (7)
C950.3116 (3)0.3391 (2)0.1446 (2)0.0739 (11)
H950.30930.29510.1750.089*
C630.9288 (2)0.3931 (2)0.04225 (15)0.0485 (7)
H630.95750.3760.00580.058*
C20.7075 (2)0.4040 (2)0.36726 (15)0.0477 (7)
C1010.3223 (3)0.4687 (2)0.06006 (19)0.0680 (10)
H1010.32620.5140.03150.082*
C10.6391 (2)0.45883 (17)0.32058 (13)0.0378 (6)
C800.7644 (3)0.2432 (2)0.15721 (19)0.0573 (8)
H80A0.78970.21280.12290.086*
H80B0.7130.21160.17080.086*
H80C0.82060.2550.20040.086*
C780.7162 (2)0.32307 (17)0.12141 (15)0.0398 (6)
H780.6880.35160.15660.048*
C680.9748 (2)0.55942 (19)0.18699 (17)0.0474 (7)
H680.93740.56660.22360.057*
C100.7700 (2)0.3432 (2)0.33904 (16)0.0533 (8)
H100.75740.35420.28640.064*
C610.9691 (2)0.45975 (19)0.08580 (15)0.0444 (7)
H611.0260.48680.07890.053*
C70.5827 (3)0.5066 (3)0.4213 (2)0.0747 (11)
H70.54070.54010.43980.09*
C30.7117 (3)0.4047 (3)0.44171 (17)0.0683 (10)
H30.75750.36970.4740.082*
C320.9316 (3)0.7327 (2)0.3226 (2)0.0608 (9)
H320.99130.73370.36240.073*
C930.4034 (3)0.3746 (2)0.1473 (2)0.0687 (10)
H930.46450.35390.17880.082*
C380.7543 (2)0.73151 (19)0.20240 (17)0.0489 (7)
C300.7775 (2)0.66640 (17)0.25219 (15)0.0378 (6)
C290.3862 (3)0.5409 (3)0.2865 (3)0.0813 (12)
H29A0.37620.48550.26930.122*
H29B0.33940.57590.25170.122*
H29C0.3730.54480.33340.122*
C490.6557 (3)0.7344 (2)0.13723 (17)0.0602 (9)
H490.62420.68010.13290.072*
C200.4974 (2)0.5667 (2)0.29460 (19)0.0575 (8)
H200.5080.5630.24580.069*
C390.8849 (3)0.5994 (2)0.37117 (18)0.0621 (10)
H390.84980.55040.34650.075*
C990.2282 (3)0.4336 (3)0.0547 (2)0.0803 (13)
H990.16820.45450.02210.096*
C360.8243 (3)0.7959 (2)0.2149 (2)0.0654 (10)
H360.81150.83970.18230.078*
C160.7336 (4)0.2559 (3)0.3459 (2)0.0894 (13)
H16A0.74510.24290.3970.134*
H16B0.77170.21870.32480.134*
H16C0.66120.25150.32030.134*
C970.2237 (3)0.3687 (3)0.0972 (2)0.0726 (11)
H970.16040.34430.09390.087*
C50.6511 (3)0.4549 (3)0.46841 (19)0.0799 (12)
H50.6560.45420.51830.096*
C840.6266 (2)0.3059 (2)0.05202 (17)0.0556 (8)
H84A0.59710.35660.03040.083*
H84B0.57470.27420.06490.083*
H84C0.65190.27610.01730.083*
C220.5144 (3)0.6550 (3)0.3193 (3)0.0905 (14)
H22A0.50070.66120.36590.136*
H22B0.46850.68940.28330.136*
H22C0.58470.67010.32440.136*
C340.9120 (3)0.7966 (2)0.2742 (2)0.0701 (11)
H340.95770.84030.28140.084*
C510.6761 (5)0.7524 (5)0.0654 (3)0.147 (3)
H51A0.70680.80550.06750.221*
H51B0.61210.75110.02630.221*
H51C0.72240.71220.05620.221*
C700.9617 (5)0.6369 (3)0.1430 (3)0.1106 (19)
H70A0.99950.6330.10750.166*
H70B0.98760.6820.17540.166*
H70C0.88970.64530.11790.166*
C120.8846 (3)0.3505 (3)0.3748 (4)0.123 (2)
H12A0.90770.40330.36450.185*
H12B0.91980.3090.35560.185*
H12C0.89950.34370.42710.185*
C410.8377 (4)0.6209 (4)0.4319 (2)0.0999 (15)
H41A0.87350.66690.45910.15*
H41B0.84370.57520.46440.15*
H41C0.7660.63440.41060.15*
C550.5776 (4)0.7942 (4)0.1506 (3)0.144 (3)
H55A0.55960.77830.19390.216*
H55B0.51660.79410.10890.216*
H55C0.6070.84790.15740.216*
C450.9986 (3)0.5785 (3)0.4041 (2)0.0965 (16)
H45A1.02870.56740.36520.145*
H45B1.00510.53120.4350.145*
H45C1.03380.62360.43290.145*
C741.0871 (3)0.5424 (3)0.2292 (3)0.127 (2)
H74A1.09080.49550.26020.191*
H74B1.11570.58880.25920.191*
H74C1.12580.53220.19510.191*
H1030.472 (3)0.459 (2)0.103 (2)0.086 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S920.0383 (4)0.0460 (4)0.0333 (3)0.0057 (3)0.0046 (3)0.0028 (3)
Si910.0260 (3)0.0334 (4)0.0309 (3)0.0021 (3)0.0086 (3)0.0014 (3)
O900.0332 (9)0.0392 (11)0.0330 (8)0.0012 (8)0.0128 (7)0.0009 (7)
O880.0330 (9)0.0374 (11)0.0376 (9)0.0040 (8)0.0090 (7)0.0064 (8)
O890.0285 (8)0.0420 (11)0.0314 (8)0.0007 (8)0.0107 (7)0.0032 (8)
C600.0326 (13)0.0379 (15)0.0372 (13)0.0019 (11)0.0127 (10)0.0054 (11)
N1030.0469 (16)0.0589 (18)0.0662 (17)0.0108 (14)0.0247 (14)0.0008 (14)
C650.0487 (16)0.0482 (18)0.0359 (14)0.0022 (13)0.0145 (12)0.0046 (12)
C590.0275 (12)0.0370 (15)0.0315 (12)0.0042 (10)0.0086 (10)0.0031 (10)
C670.0338 (13)0.0352 (15)0.0323 (12)0.0002 (11)0.0102 (10)0.0016 (11)
C90.0493 (17)0.055 (2)0.0539 (16)0.0010 (15)0.0275 (14)0.0024 (15)
C310.0366 (15)0.0458 (18)0.0553 (17)0.0001 (13)0.0077 (13)0.0163 (14)
C950.066 (2)0.064 (3)0.095 (3)0.0009 (19)0.029 (2)0.033 (2)
C630.0526 (17)0.061 (2)0.0401 (14)0.0065 (15)0.0265 (13)0.0025 (14)
C20.0491 (17)0.059 (2)0.0365 (14)0.0023 (14)0.0145 (12)0.0062 (13)
C1010.076 (2)0.078 (3)0.061 (2)0.016 (2)0.0375 (18)0.0287 (19)
C10.0364 (14)0.0467 (17)0.0346 (13)0.0008 (12)0.0173 (11)0.0002 (11)
C800.063 (2)0.045 (2)0.069 (2)0.0036 (16)0.0278 (16)0.0087 (16)
C780.0389 (14)0.0375 (16)0.0431 (14)0.0058 (12)0.0123 (12)0.0036 (12)
C680.0421 (16)0.0432 (18)0.0635 (18)0.0096 (13)0.0255 (14)0.0069 (14)
C100.0585 (19)0.058 (2)0.0450 (16)0.0169 (16)0.0170 (14)0.0150 (15)
C610.0404 (15)0.0520 (19)0.0480 (15)0.0009 (13)0.0240 (12)0.0061 (13)
C70.086 (3)0.092 (3)0.064 (2)0.008 (2)0.050 (2)0.011 (2)
C30.079 (2)0.088 (3)0.0383 (16)0.008 (2)0.0176 (16)0.0105 (17)
C320.0442 (18)0.054 (2)0.077 (2)0.0059 (15)0.0072 (16)0.0269 (19)
C930.0464 (19)0.072 (3)0.079 (2)0.0011 (17)0.0054 (17)0.022 (2)
C380.0533 (18)0.0368 (18)0.0564 (18)0.0044 (14)0.0159 (14)0.0082 (14)
C300.0348 (14)0.0319 (15)0.0476 (15)0.0006 (11)0.0135 (11)0.0107 (12)
C290.052 (2)0.077 (3)0.117 (3)0.0024 (19)0.030 (2)0.005 (2)
C490.076 (2)0.0403 (19)0.0524 (18)0.0035 (16)0.0003 (16)0.0038 (14)
C200.0505 (18)0.056 (2)0.075 (2)0.0093 (16)0.0327 (16)0.0047 (17)
C390.055 (2)0.059 (2)0.0566 (19)0.0031 (16)0.0077 (16)0.0068 (16)
C990.047 (2)0.127 (4)0.068 (2)0.021 (2)0.0182 (17)0.032 (2)
C360.077 (2)0.039 (2)0.082 (2)0.0105 (17)0.026 (2)0.0032 (17)
C160.120 (4)0.068 (3)0.087 (3)0.007 (3)0.040 (3)0.002 (2)
C970.0431 (18)0.091 (3)0.088 (3)0.0078 (19)0.0261 (18)0.010 (2)
C50.098 (3)0.106 (4)0.0430 (18)0.009 (3)0.0328 (19)0.003 (2)
C840.0471 (18)0.058 (2)0.0584 (18)0.0169 (15)0.0100 (15)0.0124 (15)
C220.064 (2)0.061 (3)0.144 (4)0.006 (2)0.027 (3)0.006 (3)
C340.061 (2)0.054 (2)0.097 (3)0.0232 (18)0.025 (2)0.026 (2)
C510.115 (4)0.249 (9)0.071 (3)0.008 (5)0.015 (3)0.043 (4)
C700.209 (6)0.046 (2)0.107 (3)0.014 (3)0.093 (4)0.009 (2)
C120.060 (3)0.110 (4)0.190 (6)0.020 (3)0.021 (3)0.045 (4)
C410.083 (3)0.132 (5)0.087 (3)0.007 (3)0.029 (2)0.028 (3)
C550.080 (3)0.202 (7)0.121 (4)0.052 (4)0.016 (3)0.040 (4)
C450.075 (3)0.119 (4)0.077 (3)0.027 (3)0.007 (2)0.009 (3)
C740.051 (2)0.125 (5)0.177 (5)0.007 (3)0.010 (3)0.089 (4)
Geometric parameters (Å, º) top
S92—Si912.0271 (9)C93—H930.93
Si91—O881.6457 (18)C38—C361.392 (5)
Si91—O891.6528 (18)C38—C301.399 (4)
Si91—O901.6552 (18)C38—C491.530 (4)
O90—C11.394 (3)C29—C201.526 (5)
O88—C301.382 (3)C29—H29A0.96
O89—C591.388 (3)C29—H29B0.96
C60—C611.388 (4)C29—H29C0.96
C60—C591.395 (4)C49—C511.498 (6)
C60—C681.514 (4)C49—C551.516 (6)
N103—C1011.305 (4)C49—H490.98
N103—C931.319 (4)C20—C221.517 (5)
N103—H1030.96 (4)C20—H200.98
C65—C631.374 (4)C39—C411.514 (6)
C65—C671.397 (4)C39—C451.519 (5)
C65—H650.93C39—H390.98
C59—C671.407 (4)C99—C971.348 (5)
C67—C781.516 (4)C99—H990.93
C9—C11.392 (4)C36—C341.374 (5)
C9—C71.409 (4)C36—H360.93
C9—C201.516 (4)C16—H16A0.96
C31—C321.380 (5)C16—H16B0.96
C31—C301.411 (4)C16—H16C0.96
C31—C391.511 (5)C97—H970.93
C95—C971.353 (5)C5—H50.93
C95—C931.357 (5)C84—H84A0.96
C95—H950.93C84—H84B0.96
C63—C611.381 (4)C84—H84C0.96
C63—H630.93C22—H22A0.96
C2—C31.398 (4)C22—H22B0.96
C2—C11.403 (4)C22—H22C0.96
C2—C101.504 (4)C34—H340.93
C101—C991.371 (5)C51—H51A0.96
C101—H1010.93C51—H51B0.96
C80—C781.530 (4)C51—H51C0.96
C80—H80A0.96C70—H70A0.96
C80—H80B0.96C70—H70B0.96
C80—H80C0.96C70—H70C0.96
C78—C841.531 (4)C12—H12A0.96
C78—H780.98C12—H12B0.96
C68—C701.502 (5)C12—H12C0.96
C68—C741.521 (5)C41—H41A0.96
C68—H680.98C41—H41B0.96
C10—C121.502 (5)C41—H41C0.96
C10—C161.531 (5)C55—H55A0.96
C10—H100.98C55—H55B0.96
C61—H610.93C55—H55C0.96
C7—C51.374 (5)C45—H45A0.96
C7—H70.93C45—H45B0.96
C3—C51.360 (5)C45—H45C0.96
C3—H30.93C74—H74A0.96
C32—C341.367 (5)C74—H74B0.96
C32—H320.93C74—H74C0.96
O88—Si91—O89106.79 (9)H29B—C29—H29C109.5
O88—Si91—O90102.29 (9)C51—C49—C55110.4 (4)
O89—Si91—O90105.55 (9)C51—C49—C38113.1 (4)
O88—Si91—S92116.67 (7)C55—C49—C38111.7 (3)
O89—Si91—S92113.32 (7)C51—C49—H49107.1
O90—Si91—S92111.11 (7)C55—C49—H49107.1
C1—O90—Si91131.61 (16)C38—C49—H49107.1
C30—O88—Si91136.18 (17)C9—C20—C22111.9 (3)
C59—O89—Si91129.85 (14)C9—C20—C29111.6 (3)
C61—C60—C59118.4 (3)C22—C20—C29110.6 (3)
C61—C60—C68119.3 (2)C9—C20—H20107.5
C59—C60—C68122.3 (2)C22—C20—H20107.5
C101—N103—C93121.7 (3)C29—C20—H20107.5
C101—N103—H103118 (2)C31—C39—C41110.6 (3)
C93—N103—H103120 (2)C31—C39—C45113.5 (3)
C63—C65—C67122.4 (3)C41—C39—C45110.0 (3)
C63—C65—H65118.8C31—C39—H39107.5
C67—C65—H65118.8C41—C39—H39107.5
O89—C59—C60117.8 (2)C45—C39—H39107.5
O89—C59—C67120.5 (2)C97—C99—C101119.4 (3)
C60—C59—C67121.7 (2)C97—C99—H99120.3
C65—C67—C59116.9 (2)C101—C99—H99120.3
C65—C67—C78118.9 (2)C34—C36—C38121.7 (4)
C59—C67—C78123.9 (2)C34—C36—H36119.1
C1—C9—C7117.1 (3)C38—C36—H36119.1
C1—C9—C20122.3 (3)C10—C16—H16A109.5
C7—C9—C20120.6 (3)C10—C16—H16B109.5
C32—C31—C30117.2 (3)H16A—C16—H16B109.5
C32—C31—C39121.5 (3)C10—C16—H16C109.5
C30—C31—C39121.3 (3)H16A—C16—H16C109.5
C97—C95—C93119.1 (3)H16B—C16—H16C109.5
C97—C95—H95120.4C99—C97—C95119.7 (4)
C93—C95—H95120.4C99—C97—H97120.2
C65—C63—C61119.1 (3)C95—C97—H97120.2
C65—C63—H63120.5C3—C5—C7119.7 (3)
C61—C63—H63120.5C3—C5—H5120.2
C3—C2—C1117.2 (3)C7—C5—H5120.2
C3—C2—C10120.4 (3)C78—C84—H84A109.5
C1—C2—C10122.4 (2)C78—C84—H84B109.5
N103—C101—C99119.8 (3)H84A—C84—H84B109.5
N103—C101—H101120.1C78—C84—H84C109.5
C99—C101—H101120.1H84A—C84—H84C109.5
C9—C1—O90118.9 (2)H84B—C84—H84C109.5
C9—C1—C2122.3 (3)C20—C22—H22A109.5
O90—C1—C2118.7 (2)C20—C22—H22B109.5
C78—C80—H80A109.5H22A—C22—H22B109.5
C78—C80—H80B109.5C20—C22—H22C109.5
H80A—C80—H80B109.5H22A—C22—H22C109.5
C78—C80—H80C109.5H22B—C22—H22C109.5
H80A—C80—H80C109.5C32—C34—C36119.7 (3)
H80B—C80—H80C109.5C32—C34—H34120.2
C67—C78—C80109.3 (2)C36—C34—H34120.2
C67—C78—C84113.3 (2)C49—C51—H51A109.5
C80—C78—C84110.5 (3)C49—C51—H51B109.5
C67—C78—H78107.8H51A—C51—H51B109.5
C80—C78—H78107.8C49—C51—H51C109.5
C84—C78—H78107.8H51A—C51—H51C109.5
C70—C68—C60111.8 (3)H51B—C51—H51C109.5
C70—C68—C74112.6 (4)C68—C70—H70A109.5
C60—C68—C74111.2 (3)C68—C70—H70B109.5
C70—C68—H68107H70A—C70—H70B109.5
C60—C68—H68107C68—C70—H70C109.5
C74—C68—H68107H70A—C70—H70C109.5
C12—C10—C2113.6 (3)H70B—C70—H70C109.5
C12—C10—C16110.5 (3)C10—C12—H12A109.5
C2—C10—C16111.1 (3)C10—C12—H12B109.5
C12—C10—H10107.1H12A—C12—H12B109.5
C2—C10—H10107.1C10—C12—H12C109.5
C16—C10—H10107.1H12A—C12—H12C109.5
C63—C61—C60121.4 (3)H12B—C12—H12C109.5
C63—C61—H61119.3C39—C41—H41A109.5
C60—C61—H61119.3C39—C41—H41B109.5
C5—C7—C9121.6 (3)H41A—C41—H41B109.5
C5—C7—H7119.2C39—C41—H41C109.5
C9—C7—H7119.2H41A—C41—H41C109.5
C5—C3—C2122.1 (3)H41B—C41—H41C109.5
C5—C3—H3118.9C49—C55—H55A109.5
C2—C3—H3118.9C49—C55—H55B109.5
C34—C32—C31122.2 (3)H55A—C55—H55B109.5
C34—C32—H32118.9C49—C55—H55C109.5
C31—C32—H32118.9H55A—C55—H55C109.5
N103—C93—C95120.3 (3)H55B—C55—H55C109.5
N103—C93—H93119.9C39—C45—H45A109.5
C95—C93—H93119.9C39—C45—H45B109.5
C36—C38—C30117.2 (3)H45A—C45—H45B109.5
C36—C38—C49120.1 (3)C39—C45—H45C109.5
C30—C38—C49122.6 (3)H45A—C45—H45C109.5
O88—C30—C38120.9 (2)H45B—C45—H45C109.5
O88—C30—C31117.0 (3)C68—C74—H74A109.5
C38—C30—C31121.9 (3)C68—C74—H74B109.5
C20—C29—H29A109.5H74A—C74—H74B109.5
C20—C29—H29B109.5C68—C74—H74C109.5
H29A—C29—H29B109.5H74A—C74—H74C109.5
C20—C29—H29C109.5H74B—C74—H74C109.5
H29A—C29—H29C109.5
O88—Si91—O90—C125.5 (2)C1—C2—C10—C16111.7 (3)
O89—Si91—O90—C186.0 (2)C65—C63—C61—C601.1 (4)
S92—Si91—O90—C1150.8 (2)C59—C60—C61—C630.3 (4)
O89—Si91—O88—C3046.9 (3)C68—C60—C61—C63178.7 (3)
O90—Si91—O88—C30157.6 (2)C1—C9—C7—C50.0 (6)
S92—Si91—O88—C3081.0 (2)C20—C9—C7—C5179.0 (4)
O88—Si91—O89—C59128.1 (2)C1—C2—C3—C51.3 (6)
O90—Si91—O89—C59123.6 (2)C10—C2—C3—C5175.4 (4)
S92—Si91—O89—C591.8 (2)C30—C31—C32—C341.7 (5)
Si91—O89—C59—C60113.3 (2)C39—C31—C32—C34175.7 (3)
Si91—O89—C59—C6770.0 (3)C101—N103—C93—C950.4 (6)
C61—C60—C59—O89179.1 (2)C97—C95—C93—N1031.6 (7)
C68—C60—C59—O890.2 (4)Si91—O88—C30—C3882.8 (3)
C61—C60—C59—C672.5 (4)Si91—O88—C30—C31101.5 (3)
C68—C60—C59—C67176.5 (2)C36—C38—C30—O88177.9 (3)
C63—C65—C67—C591.6 (4)C49—C38—C30—O880.9 (4)
C63—C65—C67—C78173.5 (3)C36—C38—C30—C312.5 (5)
O89—C59—C67—C65179.7 (2)C49—C38—C30—C31176.4 (3)
C60—C59—C67—C653.1 (4)C32—C31—C30—O88178.5 (3)
O89—C59—C67—C784.8 (4)C39—C31—C30—O881.0 (4)
C60—C59—C67—C78171.8 (2)C32—C31—C30—C382.8 (4)
C67—C65—C63—C610.4 (4)C39—C31—C30—C38174.6 (3)
C93—N103—C101—C990.8 (6)C36—C38—C49—C5152.0 (5)
C7—C9—C1—O90178.1 (3)C30—C38—C49—C51129.2 (4)
C20—C9—C1—O900.9 (4)C36—C38—C49—C5573.3 (5)
C7—C9—C1—C21.8 (5)C30—C38—C49—C55105.6 (5)
C20—C9—C1—C2177.2 (3)C1—C9—C20—C22123.2 (4)
Si91—O90—C1—C986.2 (3)C7—C9—C20—C2257.9 (5)
Si91—O90—C1—C297.3 (3)C1—C9—C20—C29112.3 (4)
C3—C2—C1—C92.4 (5)C7—C9—C20—C2966.7 (4)
C10—C2—C1—C9174.2 (3)C32—C31—C39—C4186.4 (4)
C3—C2—C1—O90178.8 (3)C30—C31—C39—C4190.9 (4)
C10—C2—C1—O902.1 (4)C32—C31—C39—C4537.7 (5)
C65—C67—C78—C8068.8 (3)C30—C31—C39—C45145.0 (3)
C59—C67—C78—C80106.0 (3)N103—C101—C99—C970.9 (6)
C65—C67—C78—C8454.9 (3)C30—C38—C36—C341.0 (5)
C59—C67—C78—C84130.3 (3)C49—C38—C36—C34177.9 (4)
C61—C60—C68—C7067.5 (4)C101—C99—C97—C950.3 (7)
C59—C60—C68—C70113.5 (4)C93—C95—C97—C991.5 (7)
C61—C60—C68—C7459.3 (4)C2—C3—C5—C70.4 (7)
C59—C60—C68—C74119.7 (4)C9—C7—C5—C31.1 (7)
C3—C2—C10—C1260.5 (5)C31—C32—C34—C360.3 (6)
C1—C2—C10—C12123.0 (4)C38—C36—C34—C320.1 (6)
C3—C2—C10—C1664.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N103—H103···S920.96 (4)2.07 (4)3.017 (3)167 (3)
(tdst_py_270) top
Crystal data top
C36H51O3SSi·C5H6NF(000) = 1456
Mr = 672.02Dx = 1.103 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9082 reflections
a = 13.5393 (17) Åθ = 3.0–29.3°
b = 16.4475 (16) ŵ = 0.15 mm1
c = 19.021 (2) ÅT = 270 K
β = 107.159 (9)°Plate, colorless
V = 4047.2 (8) Å30.38 × 0.31 × 0.15 mm
Z = 4
Data collection top
STOE IPDS 2T
diffractometer
3787 reflections with I > 2u(I)
Parabolic x-ray mirror monochromatorRint = 0.071
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.7°
rotation method scansh = 1613
23099 measured reflectionsk = 1920
7927 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0604P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
7927 reflectionsΔρmax = 0.22 e Å3
440 parametersΔρmin = 0.29 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6392 (2)0.45978 (19)0.32092 (14)0.0465 (7)
C20.7078 (3)0.4049 (2)0.36738 (16)0.0571 (9)
C30.7109 (3)0.4057 (3)0.44165 (19)0.0812 (12)
H30.75550.37010.4740.097*
C50.6513 (4)0.4563 (3)0.4681 (2)0.0963 (15)
H50.65630.4560.51790.116*
C70.5836 (3)0.5079 (3)0.4211 (2)0.0844 (12)
H70.5420.54150.43960.101*
C90.5751 (3)0.5114 (2)0.34554 (17)0.0592 (9)
C100.7702 (3)0.3442 (2)0.33953 (18)0.0641 (10)
H100.75770.35510.2870.077*
C120.8849 (4)0.3506 (4)0.3753 (4)0.138 (2)
H12A0.90730.4050.36970.207*
H12B0.92010.31310.35230.207*
H12C0.90060.33790.42670.207*
C160.7331 (4)0.2572 (3)0.3462 (3)0.1021 (15)
H16A0.74360.24440.39710.153*
H16B0.77170.21990.32570.153*
H16C0.6610.25290.31990.153*
C200.4978 (3)0.5674 (2)0.2944 (2)0.0685 (10)
H200.50820.5630.24560.082*
C220.5154 (4)0.6556 (3)0.3182 (3)0.1038 (16)
H22A0.50270.66240.36490.156*
H22B0.46920.68960.28220.156*
H22C0.58550.67050.32250.156*
C290.3863 (3)0.5423 (3)0.2864 (3)0.0958 (14)
H29A0.37590.48690.27010.144*
H29B0.33990.57690.2510.144*
H29C0.3730.54750.3330.144*
C300.7780 (2)0.66672 (18)0.25228 (16)0.0466 (7)
C310.8656 (2)0.6669 (2)0.31442 (18)0.0561 (8)
C320.9316 (3)0.7323 (3)0.3230 (2)0.0731 (11)
H320.99080.73340.36310.088*
C340.9126 (3)0.7959 (3)0.2741 (3)0.0819 (12)
H340.95880.83910.2810.098*
C360.8251 (3)0.7952 (2)0.2148 (2)0.0760 (11)
H360.81210.83890.18240.091*
C380.7550 (3)0.7308 (2)0.20209 (18)0.0573 (8)
C390.8838 (3)0.6004 (2)0.37121 (19)0.0733 (11)
H390.84780.55170.34680.088*
C410.8386 (4)0.6222 (4)0.4317 (3)0.1165 (18)
H41A0.87250.66970.45690.175*
H41B0.84810.57780.46580.175*
H41C0.76610.63310.41120.175*
C450.9976 (4)0.5784 (3)0.4038 (3)0.1144 (18)
H45A1.02690.56620.36480.172*
H45B1.00360.53160.4350.172*
H45C1.03380.62330.43210.172*
C490.6570 (3)0.7340 (2)0.13710 (19)0.0713 (11)
H490.62580.67970.13250.086*
C510.6780 (5)0.7520 (5)0.0653 (3)0.160 (3)
H51A0.70810.80520.06740.24*
H51B0.61440.75010.0260.24*
H51C0.72510.71230.05670.24*
C550.5784 (4)0.7925 (5)0.1494 (3)0.163 (3)
H55A0.56010.77670.19260.245*
H55B0.51780.79170.10760.245*
H55C0.6070.84630.1560.245*
C590.8399 (2)0.44663 (17)0.14842 (14)0.0388 (6)
C600.9260 (2)0.48751 (18)0.13918 (14)0.0436 (7)
C610.9679 (2)0.4595 (2)0.08533 (16)0.0526 (8)
H611.02490.4860.07830.063*
C630.9276 (3)0.3937 (2)0.04231 (16)0.0574 (8)
H630.95570.37690.00560.069*
C650.8450 (2)0.3526 (2)0.05375 (16)0.0519 (8)
H650.81880.30740.02490.062*
C670.7996 (2)0.37687 (18)0.10719 (14)0.0418 (7)
C680.9736 (2)0.5593 (2)0.18655 (19)0.0567 (8)
H680.93590.56670.22290.068*
C700.9634 (5)0.6363 (3)0.1433 (3)0.124 (2)
H70A1.00680.63370.11160.186*
H70B0.98390.68150.17630.186*
H70C0.89270.64330.11410.186*
C741.0859 (3)0.5430 (3)0.2286 (3)0.141 (3)
H74A1.08990.49750.2610.212*
H74B1.11490.59020.2570.212*
H74C1.1240.53110.19450.212*
C780.7160 (2)0.32381 (19)0.12179 (16)0.0480 (7)
H780.68780.35230.15680.058*
C800.7640 (3)0.2438 (2)0.1573 (2)0.0684 (10)
H80A0.7910.21430.12350.103*
H80B0.7120.21160.16940.103*
H80C0.81880.25520.20130.103*
C840.6269 (3)0.3064 (2)0.05232 (18)0.0685 (10)
H84A0.59690.35680.03080.103*
H84B0.57540.27430.06490.103*
H84C0.65260.27720.01770.103*
C930.4034 (3)0.3757 (3)0.1479 (2)0.0818 (12)
H930.46450.35580.180.098*
C950.3121 (3)0.3398 (3)0.1455 (2)0.0877 (13)
H950.30980.29570.17560.105*
C970.2242 (3)0.3698 (3)0.0979 (2)0.0858 (13)
H970.16080.3460.09480.103*
C990.2293 (3)0.4341 (3)0.0554 (2)0.0940 (15)
H990.16940.45510.02290.113*
C1010.3233 (3)0.4683 (3)0.0603 (2)0.0803 (12)
H1010.32750.5130.03130.096*
N1030.4067 (2)0.4381 (2)0.10564 (16)0.0640 (8)
O880.71080 (14)0.60160 (12)0.24456 (9)0.0435 (5)
O890.79937 (13)0.47423 (12)0.20331 (9)0.0406 (4)
O900.63215 (13)0.45945 (12)0.24599 (9)0.0414 (5)
S920.59497 (6)0.52665 (5)0.09127 (4)0.0491 (2)
Si910.68648 (5)0.51703 (5)0.19649 (4)0.03759 (19)
H1030.480 (4)0.465 (3)0.099 (2)0.132 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0452 (16)0.056 (2)0.0425 (14)0.0034 (14)0.0200 (12)0.0004 (14)
C20.061 (2)0.067 (2)0.0460 (16)0.0037 (17)0.0196 (15)0.0095 (16)
C30.094 (3)0.101 (3)0.052 (2)0.012 (3)0.026 (2)0.016 (2)
C50.119 (4)0.124 (4)0.055 (2)0.012 (3)0.039 (2)0.005 (2)
C70.099 (3)0.099 (3)0.076 (2)0.003 (3)0.058 (2)0.015 (2)
C90.061 (2)0.065 (2)0.0622 (18)0.0026 (18)0.0351 (16)0.0035 (17)
C100.071 (2)0.066 (3)0.0561 (19)0.0201 (19)0.0207 (17)0.0155 (17)
C120.066 (3)0.130 (5)0.200 (6)0.023 (3)0.011 (3)0.044 (4)
C160.130 (4)0.077 (3)0.110 (3)0.005 (3)0.052 (3)0.001 (3)
C200.062 (2)0.066 (3)0.088 (2)0.0093 (19)0.0378 (19)0.001 (2)
C220.080 (3)0.071 (3)0.162 (4)0.012 (2)0.037 (3)0.012 (3)
C290.067 (3)0.087 (3)0.140 (4)0.001 (2)0.040 (3)0.012 (3)
C300.0444 (17)0.0385 (18)0.0578 (17)0.0004 (14)0.0165 (14)0.0112 (14)
C310.0454 (18)0.051 (2)0.0661 (19)0.0008 (15)0.0072 (15)0.0174 (16)
C320.055 (2)0.064 (3)0.092 (3)0.0058 (19)0.0092 (19)0.025 (2)
C340.074 (3)0.059 (3)0.117 (3)0.027 (2)0.034 (2)0.030 (2)
C360.086 (3)0.048 (2)0.096 (3)0.012 (2)0.029 (2)0.005 (2)
C380.065 (2)0.041 (2)0.067 (2)0.0043 (16)0.0204 (17)0.0069 (16)
C390.067 (2)0.068 (3)0.065 (2)0.004 (2)0.0092 (18)0.0052 (19)
C410.100 (4)0.155 (5)0.099 (3)0.008 (3)0.037 (3)0.025 (3)
C450.092 (4)0.133 (5)0.095 (3)0.033 (3)0.008 (3)0.013 (3)
C490.089 (3)0.046 (2)0.067 (2)0.006 (2)0.0042 (19)0.0051 (17)
C510.131 (5)0.265 (9)0.076 (3)0.012 (5)0.018 (3)0.039 (4)
C550.094 (4)0.233 (8)0.131 (5)0.064 (5)0.017 (3)0.041 (5)
C590.0362 (15)0.0425 (17)0.0391 (13)0.0024 (12)0.0132 (11)0.0028 (12)
C600.0385 (15)0.0442 (18)0.0495 (15)0.0010 (13)0.0152 (12)0.0051 (13)
C610.0518 (18)0.060 (2)0.0565 (17)0.0003 (15)0.0322 (14)0.0056 (16)
C630.065 (2)0.069 (2)0.0498 (17)0.0050 (18)0.0348 (15)0.0005 (17)
C650.060 (2)0.053 (2)0.0461 (16)0.0016 (16)0.0214 (14)0.0063 (14)
C670.0408 (15)0.0433 (18)0.0417 (14)0.0008 (13)0.0127 (12)0.0025 (13)
C680.0531 (19)0.048 (2)0.078 (2)0.0087 (15)0.0323 (17)0.0072 (17)
C700.230 (7)0.051 (3)0.125 (4)0.022 (3)0.106 (4)0.009 (3)
C740.058 (3)0.142 (5)0.192 (5)0.004 (3)0.013 (3)0.091 (4)
C780.0490 (18)0.0433 (19)0.0540 (17)0.0071 (14)0.0186 (14)0.0029 (14)
C800.074 (2)0.052 (2)0.084 (2)0.0030 (19)0.0320 (19)0.0084 (19)
C840.061 (2)0.072 (3)0.069 (2)0.0187 (19)0.0131 (18)0.0136 (18)
C930.060 (2)0.083 (3)0.093 (3)0.002 (2)0.009 (2)0.024 (2)
C950.078 (3)0.077 (3)0.112 (3)0.005 (2)0.033 (3)0.035 (3)
C970.051 (2)0.105 (4)0.104 (3)0.011 (2)0.026 (2)0.013 (3)
C990.056 (2)0.140 (4)0.085 (3)0.019 (3)0.019 (2)0.041 (3)
C1010.089 (3)0.095 (3)0.071 (2)0.016 (3)0.044 (2)0.035 (2)
N1030.0568 (18)0.067 (2)0.0738 (19)0.0095 (16)0.0283 (15)0.0018 (16)
O880.0407 (11)0.0421 (12)0.0472 (10)0.0051 (9)0.0122 (8)0.0082 (9)
O890.0344 (9)0.0506 (13)0.0388 (9)0.0006 (9)0.0138 (7)0.0026 (9)
O900.0393 (10)0.0476 (13)0.0403 (9)0.0015 (9)0.0163 (8)0.0021 (8)
S920.0458 (4)0.0547 (5)0.0426 (4)0.0065 (4)0.0064 (3)0.0030 (4)
Si910.0331 (4)0.0415 (5)0.0385 (4)0.0024 (4)0.0112 (3)0.0013 (3)
Geometric parameters (Å, º) top
C1—C91.391 (4)C49—H490.98
C1—O901.400 (3)C51—H51A0.96
C1—C21.404 (4)C51—H51B0.96
C2—C31.401 (4)C51—H51C0.96
C2—C101.502 (5)C55—H55A0.96
C3—C51.355 (6)C55—H55B0.96
C3—H30.93C55—H55C0.96
C5—C71.370 (6)C59—O891.391 (3)
C5—H50.93C59—C601.401 (4)
C7—C91.408 (5)C59—C671.406 (4)
C7—H70.93C60—C611.389 (4)
C9—C201.512 (5)C60—C681.509 (4)
C10—C121.505 (6)C61—C631.369 (4)
C10—C161.534 (6)C61—H610.93
C10—H100.98C63—C651.378 (4)
C12—H12A0.96C63—H630.93
C12—H12B0.96C65—C671.392 (4)
C12—H12C0.96C65—H650.93
C16—H16A0.96C67—C781.519 (4)
C16—H16B0.96C68—C701.496 (5)
C16—H16C0.96C68—C741.519 (5)
C20—C221.518 (5)C68—H680.98
C20—C291.529 (5)C70—H70A0.96
C20—H200.98C70—H70B0.96
C22—H22A0.96C70—H70C0.96
C22—H22B0.96C74—H74A0.96
C22—H22C0.96C74—H74B0.96
C29—H29A0.96C74—H74C0.96
C29—H29B0.96C78—C841.531 (4)
C29—H29C0.96C78—C801.534 (4)
C30—O881.385 (3)C78—H780.98
C30—C381.394 (4)C80—H80A0.96
C30—C311.406 (4)C80—H80B0.96
C31—C321.377 (5)C80—H80C0.96
C31—C391.506 (5)C84—H84A0.96
C32—C341.373 (6)C84—H84B0.96
C32—H320.93C84—H84C0.96
C34—C361.374 (5)C93—N1031.313 (5)
C34—H340.93C93—C951.360 (5)
C36—C381.395 (5)C93—H930.93
C36—H360.93C95—C971.356 (5)
C38—C491.524 (5)C95—H950.93
C39—C411.499 (6)C97—C991.345 (6)
C39—C451.524 (5)C97—H970.93
C39—H390.98C99—C1011.370 (6)
C41—H41A0.96C99—H990.93
C41—H41B0.96C101—N1031.301 (5)
C41—H41C0.96C101—H1010.93
C45—H45A0.96N103—H1031.12 (5)
C45—H45B0.96O88—Si911.644 (2)
C45—H45C0.96O89—Si911.6528 (19)
C49—C551.504 (7)O90—Si911.6533 (19)
C49—C511.505 (6)S92—Si912.0254 (10)
C9—C1—O90118.9 (3)C38—C49—H49106.9
C9—C1—C2122.9 (3)C49—C51—H51A109.5
O90—C1—C2118.2 (3)C49—C51—H51B109.5
C3—C2—C1116.5 (3)H51A—C51—H51B109.5
C3—C2—C10120.6 (3)C49—C51—H51C109.5
C1—C2—C10122.8 (3)H51A—C51—H51C109.5
C5—C3—C2122.4 (4)H51B—C51—H51C109.5
C5—C3—H3118.8C49—C55—H55A109.5
C2—C3—H3118.8C49—C55—H55B109.5
C3—C5—C7119.7 (4)H55A—C55—H55B109.5
C3—C5—H5120.1C49—C55—H55C109.5
C7—C5—H5120.1H55A—C55—H55C109.5
C5—C7—C9121.9 (4)H55B—C55—H55C109.5
C5—C7—H7119O89—C59—C60117.7 (2)
C9—C7—H7119O89—C59—C67120.8 (2)
C1—C9—C7116.5 (3)C60—C59—C67121.4 (3)
C1—C9—C20122.5 (3)C61—C60—C59118.0 (3)
C7—C9—C20121.0 (3)C61—C60—C68120.3 (3)
C2—C10—C12114.0 (3)C59—C60—C68121.7 (3)
C2—C10—C16111.1 (3)C63—C61—C60121.7 (3)
C12—C10—C16110.3 (4)C63—C61—H61119.2
C2—C10—H10107C60—C61—H61119.2
C12—C10—H10107C61—C63—C65119.5 (3)
C16—C10—H10107C61—C63—H63120.2
C10—C12—H12A109.5C65—C63—H63120.2
C10—C12—H12B109.5C63—C65—C67121.9 (3)
H12A—C12—H12B109.5C63—C65—H65119.1
C10—C12—H12C109.5C67—C65—H65119.1
H12A—C12—H12C109.5C65—C67—C59117.4 (3)
H12B—C12—H12C109.5C65—C67—C78118.8 (3)
C10—C16—H16A109.5C59—C67—C78123.6 (3)
C10—C16—H16B109.5C70—C68—C60112.3 (3)
H16A—C16—H16B109.5C70—C68—C74110.8 (4)
C10—C16—H16C109.5C60—C68—C74111.2 (3)
H16A—C16—H16C109.5C70—C68—H68107.4
H16B—C16—H16C109.5C60—C68—H68107.4
C9—C20—C22111.8 (3)C74—C68—H68107.4
C9—C20—C29112.1 (3)C68—C70—H70A109.5
C22—C20—C29110.5 (3)C68—C70—H70B109.5
C9—C20—H20107.4H70A—C70—H70B109.5
C22—C20—H20107.4C68—C70—H70C109.5
C29—C20—H20107.4H70A—C70—H70C109.5
C20—C22—H22A109.5H70B—C70—H70C109.5
C20—C22—H22B109.5C68—C74—H74A109.5
H22A—C22—H22B109.5C68—C74—H74B109.5
C20—C22—H22C109.5H74A—C74—H74B109.5
H22A—C22—H22C109.5C68—C74—H74C109.5
H22B—C22—H22C109.5H74A—C74—H74C109.5
C20—C29—H29A109.5H74B—C74—H74C109.5
C20—C29—H29B109.5C67—C78—C84112.9 (3)
H29A—C29—H29B109.5C67—C78—C80109.4 (3)
C20—C29—H29C109.5C84—C78—C80110.1 (3)
H29A—C29—H29C109.5C67—C78—H78108.1
H29B—C29—H29C109.5C84—C78—H78108.1
O88—C30—C38120.3 (3)C80—C78—H78108.1
O88—C30—C31117.1 (3)C78—C80—H80A109.5
C38—C30—C31122.5 (3)C78—C80—H80B109.5
C32—C31—C30117.3 (3)H80A—C80—H80B109.5
C32—C31—C39121.3 (3)C78—C80—H80C109.5
C30—C31—C39121.4 (3)H80A—C80—H80C109.5
C34—C32—C31122.0 (3)H80B—C80—H80C109.5
C34—C32—H32119C78—C84—H84A109.5
C31—C32—H32119C78—C84—H84B109.5
C32—C34—C36119.6 (4)H84A—C84—H84B109.5
C32—C34—H34120.2C78—C84—H84C109.5
C36—C34—H34120.2H84A—C84—H84C109.5
C34—C36—C38121.8 (4)H84B—C84—H84C109.5
C34—C36—H36119.1N103—C93—C95120.9 (4)
C38—C36—H36119.1N103—C93—H93119.5
C30—C38—C36116.8 (3)C95—C93—H93119.5
C30—C38—C49123.2 (3)C97—C95—C93118.3 (4)
C36—C38—C49120.0 (3)C97—C95—H95120.8
C41—C39—C31111.1 (4)C93—C95—H95120.8
C41—C39—C45109.7 (3)C99—C97—C95119.8 (4)
C31—C39—C45113.4 (4)C99—C97—H97120.1
C41—C39—H39107.5C95—C97—H97120.1
C31—C39—H39107.5C97—C99—C101119.6 (4)
C45—C39—H39107.5C97—C99—H99120.2
C39—C41—H41A109.5C101—C99—H99120.2
C39—C41—H41B109.5N103—C101—C99119.7 (4)
H41A—C41—H41B109.5N103—C101—H101120.2
C39—C41—H41C109.5C99—C101—H101120.2
H41A—C41—H41C109.5C101—N103—C93121.7 (4)
H41B—C41—H41C109.5C101—N103—H103113 (2)
C39—C45—H45A109.5C93—N103—H103125 (2)
C39—C45—H45B109.5C30—O88—Si91136.96 (18)
H45A—C45—H45B109.5C59—O89—Si91129.81 (15)
C39—C45—H45C109.5C1—O90—Si91132.00 (18)
H45A—C45—H45C109.5O88—Si91—O89106.73 (10)
H45B—C45—H45C109.5O88—Si91—O90102.57 (10)
C55—C49—C51110.3 (5)O89—Si91—O90105.53 (10)
C55—C49—C38112.5 (3)O88—Si91—S92116.57 (8)
C51—C49—C38113.0 (4)O89—Si91—S92113.13 (7)
C55—C49—H49106.9O90—Si91—S92111.24 (7)
C51—C49—H49106.9
C9—C1—C2—C31.5 (5)O89—C59—C60—C61178.9 (2)
O90—C1—C2—C3178.5 (3)C67—C59—C60—C613.1 (4)
C9—C1—C2—C10174.5 (3)O89—C59—C60—C680.2 (4)
O90—C1—C2—C102.5 (5)C67—C59—C60—C68176.1 (3)
C1—C2—C3—C50.0 (6)C59—C60—C61—C630.3 (4)
C10—C2—C3—C5176.1 (4)C68—C60—C61—C63178.9 (3)
C2—C3—C5—C71.4 (7)C60—C61—C63—C651.8 (5)
C3—C5—C7—C91.4 (7)C61—C63—C65—C671.2 (5)
O90—C1—C9—C7178.4 (3)C63—C65—C67—C591.5 (4)
C2—C1—C9—C71.5 (5)C63—C65—C67—C78174.0 (3)
O90—C1—C9—C200.0 (5)O89—C59—C67—C65179.4 (2)
C2—C1—C9—C20177.0 (3)C60—C59—C67—C653.6 (4)
C5—C7—C9—C10.0 (6)O89—C59—C67—C784.2 (4)
C5—C7—C9—C20178.4 (4)C60—C59—C67—C78171.6 (3)
C3—C2—C10—C1260.9 (5)C61—C60—C68—C7066.0 (4)
C1—C2—C10—C12123.3 (4)C59—C60—C68—C70114.8 (4)
C3—C2—C10—C1664.5 (5)C61—C60—C68—C7458.8 (5)
C1—C2—C10—C16111.3 (4)C59—C60—C68—C74120.3 (4)
C1—C9—C20—C22123.0 (4)C65—C67—C78—C8454.7 (4)
C7—C9—C20—C2258.6 (5)C59—C67—C78—C84130.2 (3)
C1—C9—C20—C29112.3 (4)C65—C67—C78—C8068.3 (3)
C7—C9—C20—C2966.1 (5)C59—C67—C78—C80106.8 (3)
O88—C30—C31—C32178.8 (3)N103—C93—C95—C970.3 (7)
C38—C30—C31—C322.5 (5)C93—C95—C97—C990.7 (7)
O88—C30—C31—C391.7 (5)C95—C97—C99—C1010.4 (8)
C38—C30—C31—C39174.7 (3)C97—C99—C101—N1030.4 (7)
C30—C31—C32—C341.2 (6)C99—C101—N103—C930.8 (6)
C39—C31—C32—C34175.9 (4)C95—C93—N103—C1010.5 (7)
C31—C32—C34—C360.4 (6)C38—C30—O88—Si9182.4 (4)
C32—C34—C36—C381.0 (6)C31—C30—O88—Si91101.1 (3)
O88—C30—C38—C36178.2 (3)C60—C59—O89—Si91113.6 (2)
C31—C30—C38—C361.9 (5)C67—C59—O89—Si9170.5 (3)
O88—C30—C38—C490.2 (5)C9—C1—O90—Si9185.2 (3)
C31—C30—C38—C49176.1 (3)C2—C1—O90—Si9197.7 (3)
C34—C36—C38—C300.1 (6)C30—O88—Si91—O8946.1 (3)
C34—C36—C38—C49177.9 (4)C30—O88—Si91—O90156.8 (3)
C32—C31—C39—C4185.3 (5)C30—O88—Si91—S9281.4 (3)
C30—C31—C39—C4191.8 (4)C59—O89—Si91—O88127.8 (2)
C32—C31—C39—C4538.9 (5)C59—O89—Si91—O90123.6 (2)
C30—C31—C39—C45144.1 (4)C59—O89—Si91—S921.7 (3)
C30—C38—C49—C55104.5 (5)C1—O90—Si91—O8824.9 (3)
C36—C38—C49—C5573.4 (6)C1—O90—Si91—O8986.7 (2)
C30—C38—C49—C51129.8 (5)C1—O90—Si91—S92150.3 (2)
C36—C38—C49—C5152.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N103—H103···S921.12 (5)1.90 (5)3.017 (3)172 (4)
 

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