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
| 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 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_90sup2.hkl Contains datablock tdst_et3n_90 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_120sup3.hkl Contains datablock tdst_et3n_120 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_150sup4.hkl Contains datablock tdst_et3n_150 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_165sup5.hkl Contains datablock tdst_et3n_165 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_180sup6.hkl Contains datablock tdst_et3n_180 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_210sup7.hkl Contains datablock tdst_et3n_210 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_et3n_temp_240sup8.hkl Contains datablock tdst_et3n_temp_240 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_temp_90sup9.hkl Contains datablock tdst_py_temp_90 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_120sup10.hkl Contains datablock tdst_py_120 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_150sup11.hkl Contains datablock tdst_py_150 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_180ksup12.hkl Contains datablock tdst_py_180k |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_210sup13.hkl Contains datablock tdst_py_210 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_240sup14.hkl Contains datablock tdst_py_240 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011562/eb5051tdst_py_270sup15.hkl Contains datablock tdst_py_270 |
| 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
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).
Crystal data top
C42H67NO3SSi | F(000) = 1520 |
Mr = 694.11 | Dx = 1.123 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 1642 reflections |
a = 11.6341 (17) Å | θ = 3.4–29.4° |
b = 17.8996 (16) Å | µ = 0.15 mm−1 |
c = 20.096 (3) Å | T = 90 K |
β = 101.098 (12)° | Block, colourless |
V = 4106.7 (9) Å3 | 0.34 × 0.22 × 0.13 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 5341 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.084 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.1° |
rotation method scans | h = −14→13 |
13602 measured reflections | k = −22→22 |
7538 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 0.88 | Δρmax = 0.33 e Å−3 |
7538 reflections | Δρmin = −0.25 e Å−3 |
452 parameters | Absolute structure: Flack x determined using 1785 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
Si1 | 0.55624 (10) | 0.26080 (7) | 0.06091 (7) | 0.0109 (3) | |
S114 | 0.40718 (10) | 0.20800 (7) | 0.01637 (7) | 0.0156 (3) | |
O112 | 0.5472 (3) | 0.35280 (17) | 0.05841 (17) | 0.0135 (7) | |
O110 | 0.5925 (3) | 0.23785 (18) | 0.14274 (16) | 0.0139 (7) | |
O111 | 0.6746 (3) | 0.24698 (18) | 0.02831 (16) | 0.0138 (7) | |
N109 | 0.1974 (3) | 0.2845 (2) | −0.0753 (2) | 0.0168 (9) | |
H115 | 0.280 (5) | 0.271 (3) | −0.049 (3) | 0.035 (17)* | |
C38 | 0.7322 (4) | 0.1431 (3) | −0.0344 (2) | 0.0143 (10) | |
C78 | 0.5840 (4) | 0.3837 (3) | −0.0782 (3) | 0.0171 (11) | |
H79 | 0.5379 | 0.343 | −0.064 | 0.02* | |
C1 | 0.5327 (4) | 0.1953 (3) | 0.1825 (2) | 0.0142 (10) | |
C5 | 0.4228 (4) | 0.1103 (3) | 0.2679 (2) | 0.0175 (11) | |
H6 | 0.3857 | 0.0817 | 0.2962 | 0.021* | |
C31 | 0.8584 (4) | 0.1882 (3) | 0.0700 (2) | 0.0143 (10) | |
C2 | 0.4377 (4) | 0.2260 (3) | 0.2066 (2) | 0.0144 (10) | |
C39 | 0.8832 (4) | 0.2455 (3) | 0.1280 (2) | 0.0156 (10) | |
H40 | 0.8085 | 0.258 | 0.1409 | 0.019* | |
C45 | 0.9330 (4) | 0.3174 (3) | 0.1022 (3) | 0.0213 (12) | |
H46 | 1.0065 | 0.3065 | 0.0892 | 0.032* | |
H47 | 0.9448 | 0.3542 | 0.1376 | 0.032* | |
H48 | 0.8789 | 0.3363 | 0.0638 | 0.032* | |
C10 | 0.3943 (4) | 0.3050 (3) | 0.1915 (2) | 0.0158 (11) | |
H11 | 0.4326 | 0.3248 | 0.1558 | 0.019* | |
C41 | 0.9653 (4) | 0.2154 (3) | 0.1908 (3) | 0.0222 (12) | |
H42 | 0.9367 | 0.1681 | 0.2032 | 0.033* | |
H43 | 0.9684 | 0.25 | 0.2276 | 0.033* | |
H44 | 1.0424 | 0.2091 | 0.1811 | 0.033* | |
C22 | 0.6274 (5) | 0.0514 (3) | 0.1047 (3) | 0.0232 (12) | |
H23 | 0.5843 | 0.0076 | 0.1124 | 0.035* | |
H24 | 0.6916 | 0.0374 | 0.0836 | 0.035* | |
H25 | 0.5768 | 0.0851 | 0.0755 | 0.035* | |
C34 | 0.9232 (4) | 0.0865 (3) | 0.0073 (3) | 0.0210 (12) | |
H35 | 0.9794 | 0.051 | 0.0024 | 0.025* | |
C20 | 0.6745 (4) | 0.0899 (3) | 0.1722 (3) | 0.0151 (10) | |
H21 | 0.7243 | 0.1314 | 0.1632 | 0.018* | |
C3 | 0.3839 (4) | 0.1815 (3) | 0.2494 (2) | 0.0167 (11) | |
H4 | 0.3202 | 0.2006 | 0.2656 | 0.02* | |
C84 | 0.4998 (5) | 0.4393 (3) | −0.1200 (3) | 0.0244 (12) | |
H85 | 0.5431 | 0.4814 | −0.1317 | 0.037* | |
H86 | 0.4436 | 0.456 | −0.0939 | 0.037* | |
H87 | 0.4597 | 0.4154 | −0.1607 | 0.037* | |
C95 | 0.1071 (4) | 0.2506 (3) | −0.0396 (3) | 0.0195 (11) | |
H96 | 0.1264 | 0.264 | 0.008 | 0.023* | |
H97 | 0.1116 | 0.1967 | −0.0426 | 0.023* | |
C30 | 0.7529 (4) | 0.1911 (3) | 0.0219 (2) | 0.0134 (10) | |
C61 | 0.7660 (4) | 0.5021 (3) | 0.0976 (3) | 0.0212 (12) | |
H62 | 0.8037 | 0.5293 | 0.1348 | 0.025* | |
C32 | 0.9410 (4) | 0.1358 (3) | 0.0619 (3) | 0.0197 (11) | |
H33 | 1.0104 | 0.1332 | 0.0937 | 0.024* | |
C68 | 0.6605 (4) | 0.4337 (3) | 0.1774 (2) | 0.0161 (11) | |
H69 | 0.6072 | 0.391 | 0.175 | 0.019* | |
C70 | 0.7713 (5) | 0.4154 (3) | 0.2297 (3) | 0.0220 (12) | |
H71 | 0.8072 | 0.3712 | 0.2159 | 0.033* | |
H72 | 0.7509 | 0.4071 | 0.2732 | 0.033* | |
H73 | 0.8253 | 0.4564 | 0.2328 | 0.033* | |
C105 | 0.2222 (5) | 0.3985 (3) | −0.0029 (3) | 0.0265 (13) | |
H106 | 0.2298 | 0.4519 | −0.0043 | 0.04* | |
H107 | 0.293 | 0.3774 | 0.0225 | 0.04* | |
H108 | 0.1577 | 0.3859 | 0.0185 | 0.04* | |
C9 | 0.5741 (4) | 0.1226 (3) | 0.2008 (2) | 0.0140 (10) | |
C91 | 0.2930 (5) | 0.2676 (3) | −0.1766 (3) | 0.0267 (13) | |
H92 | 0.2835 | 0.2427 | −0.2196 | 0.04* | |
H93 | 0.3612 | 0.2485 | −0.1469 | 0.04* | |
H94 | 0.3019 | 0.3203 | −0.1829 | 0.04* | |
C16 | 0.2618 (4) | 0.3091 (3) | 0.1655 (3) | 0.0208 (12) | |
H17 | 0.2401 | 0.2754 | 0.128 | 0.031* | |
H18 | 0.2404 | 0.3591 | 0.1511 | 0.031* | |
H19 | 0.2219 | 0.2952 | 0.2013 | 0.031* | |
C60 | 0.6863 (4) | 0.4466 (3) | 0.1070 (3) | 0.0172 (11) | |
C36 | 0.8195 (4) | 0.0918 (3) | −0.0397 (3) | 0.0188 (11) | |
H37 | 0.8077 | 0.0595 | −0.0766 | 0.023* | |
C88 | 0.1862 (4) | 0.2538 (3) | −0.1457 (3) | 0.0199 (11) | |
H89 | 0.1185 | 0.2764 | −0.1744 | 0.024* | |
H90 | 0.1723 | 0.2005 | −0.1446 | 0.024* | |
C12 | 0.4301 (4) | 0.3547 (3) | 0.2547 (3) | 0.0185 (11) | |
H13 | 0.3975 | 0.3348 | 0.2913 | 0.028* | |
H14 | 0.401 | 0.4045 | 0.2446 | 0.028* | |
H15 | 0.5139 | 0.356 | 0.2675 | 0.028* | |
C65 | 0.7323 (4) | 0.4777 (3) | −0.0212 (3) | 0.0205 (12) | |
H66 | 0.748 | 0.4883 | −0.0639 | 0.025* | |
C80 | 0.6655 (5) | 0.3508 (3) | −0.1219 (3) | 0.0255 (13) | |
H81 | 0.6197 | 0.3271 | −0.161 | 0.038* | |
H82 | 0.7163 | 0.3146 | −0.096 | 0.038* | |
H83 | 0.7116 | 0.39 | −0.1361 | 0.038* | |
C98 | −0.0176 (4) | 0.2747 (3) | −0.0676 (3) | 0.0247 (12) | |
H99 | −0.0356 | 0.2656 | −0.1156 | 0.037* | |
H100 | −0.0259 | 0.327 | −0.0592 | 0.037* | |
H101 | −0.0704 | 0.2467 | −0.0459 | 0.037* | |
C167 | 0.6512 (4) | 0.4221 (3) | −0.0151 (2) | 0.0159 (11) | |
C59 | 0.6306 (4) | 0.4062 (3) | 0.0502 (3) | 0.0133 (10) | |
C26 | 0.7512 (5) | 0.0359 (3) | 0.2201 (3) | 0.0262 (13) | |
H27 | 0.7086 | −0.0095 | 0.2234 | 0.039* | |
H28 | 0.7724 | 0.0582 | 0.2642 | 0.039* | |
H29 | 0.8207 | 0.0249 | 0.2028 | 0.039* | |
C7 | 0.5177 (4) | 0.0821 (3) | 0.2440 (2) | 0.0160 (11) | |
H8 | 0.5446 | 0.0344 | 0.2572 | 0.019* | |
C74 | 0.5977 (5) | 0.5026 (3) | 0.1994 (3) | 0.0268 (13) | |
H75 | 0.5791 | 0.4937 | 0.2433 | 0.04* | |
H76 | 0.5268 | 0.5116 | 0.1671 | 0.04* | |
H77 | 0.648 | 0.5454 | 0.2016 | 0.04* | |
C63 | 0.7901 (5) | 0.5176 (3) | 0.0344 (3) | 0.0222 (12) | |
H64 | 0.8445 | 0.5542 | 0.0292 | 0.027* | |
C102 | 0.2000 (5) | 0.3678 (3) | −0.0743 (3) | 0.0188 (11) | |
H103 | 0.1258 | 0.3868 | −0.0989 | 0.023* | |
H104 | 0.2611 | 0.3852 | −0.0973 | 0.023* | |
C49 | 0.6212 (4) | 0.1456 (3) | −0.0887 (3) | 0.0173 (11) | |
H50 | 0.5759 | 0.1896 | −0.0803 | 0.021* | |
C55 | 0.5442 (5) | 0.0765 (3) | −0.0872 (3) | 0.0222 (12) | |
H56 | 0.5864 | 0.0328 | −0.0961 | 0.033* | |
H57 | 0.4743 | 0.0813 | −0.1212 | 0.033* | |
H58 | 0.5236 | 0.0722 | −0.0433 | 0.033* | |
C51 | 0.6506 (5) | 0.1535 (3) | −0.1600 (3) | 0.0239 (12) | |
H52 | 0.6996 | 0.1964 | −0.1611 | 0.036* | |
H53 | 0.5794 | 0.1594 | −0.1929 | 0.036* | |
H54 | 0.6909 | 0.1095 | −0.1705 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0101 (6) | 0.0125 (7) | 0.0098 (7) | −0.0003 (6) | 0.0012 (5) | 0.0000 (6) |
S114 | 0.0122 (6) | 0.0158 (6) | 0.0169 (7) | −0.0023 (5) | −0.0022 (5) | 0.0001 (5) |
O112 | 0.0111 (16) | 0.0179 (18) | 0.0112 (17) | −0.0007 (15) | 0.0015 (13) | −0.0005 (15) |
O110 | 0.0148 (16) | 0.0166 (18) | 0.0105 (17) | −0.0031 (14) | 0.0032 (13) | 0.0030 (14) |
O111 | 0.0132 (16) | 0.0160 (18) | 0.0125 (17) | 0.0028 (13) | 0.0028 (13) | 0.0005 (14) |
N109 | 0.014 (2) | 0.022 (2) | 0.013 (2) | −0.0006 (18) | −0.0002 (17) | 0.0007 (18) |
C38 | 0.015 (2) | 0.013 (3) | 0.014 (3) | 0.002 (2) | 0.001 (2) | 0.001 (2) |
C78 | 0.021 (3) | 0.015 (3) | 0.014 (3) | −0.002 (2) | 0.002 (2) | −0.002 (2) |
C1 | 0.016 (2) | 0.015 (3) | 0.010 (2) | −0.0069 (19) | −0.0011 (19) | −0.001 (2) |
C5 | 0.023 (3) | 0.019 (3) | 0.011 (3) | −0.010 (2) | 0.004 (2) | 0.000 (2) |
C31 | 0.014 (2) | 0.013 (2) | 0.015 (3) | −0.0010 (19) | 0.0019 (19) | 0.001 (2) |
C2 | 0.013 (2) | 0.017 (3) | 0.010 (2) | −0.0046 (19) | −0.0047 (19) | −0.001 (2) |
C39 | 0.015 (2) | 0.016 (3) | 0.015 (2) | −0.001 (2) | −0.0001 (19) | −0.001 (2) |
C45 | 0.017 (3) | 0.025 (3) | 0.021 (3) | −0.001 (2) | 0.002 (2) | −0.007 (2) |
C10 | 0.016 (2) | 0.022 (3) | 0.011 (2) | 0.004 (2) | 0.0051 (19) | 0.003 (2) |
C41 | 0.023 (3) | 0.031 (3) | 0.012 (3) | −0.002 (2) | 0.000 (2) | −0.003 (2) |
C22 | 0.024 (3) | 0.021 (3) | 0.025 (3) | 0.005 (2) | 0.005 (2) | −0.001 (2) |
C34 | 0.019 (3) | 0.015 (3) | 0.029 (3) | 0.007 (2) | 0.003 (2) | 0.001 (2) |
C20 | 0.016 (2) | 0.009 (2) | 0.021 (3) | 0.0012 (19) | 0.005 (2) | 0.001 (2) |
C3 | 0.014 (2) | 0.023 (3) | 0.013 (3) | −0.003 (2) | 0.004 (2) | −0.004 (2) |
C84 | 0.025 (3) | 0.021 (3) | 0.025 (3) | 0.003 (2) | −0.003 (2) | −0.003 (2) |
C95 | 0.020 (3) | 0.022 (3) | 0.016 (3) | −0.001 (2) | 0.001 (2) | 0.003 (2) |
C30 | 0.012 (2) | 0.014 (3) | 0.014 (3) | 0.0011 (19) | 0.0035 (19) | 0.006 (2) |
C61 | 0.023 (3) | 0.022 (3) | 0.015 (3) | −0.007 (2) | −0.005 (2) | −0.004 (2) |
C32 | 0.019 (3) | 0.020 (3) | 0.018 (3) | 0.004 (2) | −0.001 (2) | 0.002 (2) |
C68 | 0.018 (3) | 0.016 (3) | 0.014 (3) | −0.003 (2) | 0.002 (2) | −0.003 (2) |
C70 | 0.028 (3) | 0.023 (3) | 0.014 (3) | 0.000 (2) | 0.002 (2) | 0.002 (2) |
C105 | 0.040 (3) | 0.016 (3) | 0.023 (3) | 0.001 (2) | 0.004 (3) | −0.001 (2) |
C9 | 0.013 (2) | 0.016 (3) | 0.011 (3) | 0.0002 (19) | −0.0037 (19) | −0.003 (2) |
C91 | 0.031 (3) | 0.033 (3) | 0.016 (3) | −0.002 (3) | 0.005 (2) | −0.006 (2) |
C16 | 0.018 (3) | 0.028 (3) | 0.015 (3) | 0.004 (2) | 0.001 (2) | 0.001 (2) |
C60 | 0.020 (3) | 0.017 (3) | 0.013 (3) | 0.001 (2) | 0.001 (2) | −0.001 (2) |
C36 | 0.020 (3) | 0.020 (3) | 0.016 (3) | 0.003 (2) | 0.003 (2) | −0.005 (2) |
C88 | 0.024 (3) | 0.021 (3) | 0.015 (3) | 0.003 (2) | 0.005 (2) | −0.002 (2) |
C12 | 0.018 (3) | 0.017 (3) | 0.019 (3) | 0.003 (2) | 0.000 (2) | 0.002 (2) |
C65 | 0.023 (3) | 0.021 (3) | 0.017 (3) | −0.002 (2) | 0.004 (2) | 0.004 (2) |
C80 | 0.024 (3) | 0.032 (3) | 0.019 (3) | −0.001 (2) | 0.002 (2) | −0.007 (2) |
C98 | 0.019 (3) | 0.037 (3) | 0.019 (3) | −0.002 (2) | 0.005 (2) | 0.004 (3) |
C167 | 0.013 (2) | 0.018 (3) | 0.016 (3) | 0.001 (2) | 0.000 (2) | −0.005 (2) |
C59 | 0.011 (2) | 0.010 (2) | 0.018 (3) | 0.0000 (19) | 0.001 (2) | 0.000 (2) |
C26 | 0.024 (3) | 0.029 (3) | 0.024 (3) | 0.008 (2) | −0.001 (2) | −0.004 (3) |
C7 | 0.023 (3) | 0.010 (3) | 0.014 (3) | −0.002 (2) | 0.001 (2) | 0.000 (2) |
C74 | 0.033 (3) | 0.030 (3) | 0.019 (3) | 0.004 (2) | 0.010 (3) | −0.002 (3) |
C63 | 0.023 (3) | 0.017 (3) | 0.026 (3) | −0.008 (2) | 0.003 (2) | −0.002 (2) |
C102 | 0.027 (3) | 0.016 (3) | 0.015 (3) | 0.002 (2) | 0.006 (2) | −0.002 (2) |
C49 | 0.017 (3) | 0.019 (3) | 0.016 (3) | 0.006 (2) | 0.001 (2) | −0.004 (2) |
C55 | 0.025 (3) | 0.023 (3) | 0.016 (3) | 0.001 (2) | −0.001 (2) | −0.004 (2) |
C51 | 0.029 (3) | 0.026 (3) | 0.017 (3) | 0.008 (2) | 0.005 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
Si1—O112 | 1.650 (3) | C61—C60 | 1.395 (7) |
Si1—O111 | 1.654 (3) | C61—H62 | 0.93 |
Si1—O110 | 1.669 (3) | C32—H33 | 0.93 |
Si1—S114 | 2.0258 (18) | C68—C60 | 1.520 (7) |
O112—C59 | 1.394 (6) | C68—C70 | 1.534 (7) |
O110—C1 | 1.383 (6) | C68—C74 | 1.541 (7) |
O111—C30 | 1.376 (6) | C68—H69 | 0.98 |
N109—C102 | 1.492 (7) | C70—H71 | 0.96 |
N109—C88 | 1.498 (6) | C70—H72 | 0.96 |
N109—C95 | 1.509 (6) | C70—H73 | 0.96 |
N109—H115 | 1.03 (6) | C105—C102 | 1.511 (7) |
C38—C36 | 1.387 (7) | C105—H106 | 0.96 |
C38—C30 | 1.403 (7) | C105—H107 | 0.96 |
C38—C49 | 1.523 (7) | C105—H108 | 0.96 |
C78—C167 | 1.519 (7) | C9—C7 | 1.389 (7) |
C78—C80 | 1.529 (7) | C91—C88 | 1.513 (7) |
C78—C84 | 1.530 (7) | C91—H92 | 0.96 |
C78—H79 | 0.98 | C91—H93 | 0.96 |
C1—C2 | 1.401 (7) | C91—H94 | 0.96 |
C1—C9 | 1.412 (7) | C16—H17 | 0.96 |
C5—C3 | 1.380 (7) | C16—H18 | 0.96 |
C5—C7 | 1.382 (7) | C16—H19 | 0.96 |
C5—H6 | 0.93 | C60—C59 | 1.402 (7) |
C31—C32 | 1.374 (7) | C36—H37 | 0.93 |
C31—C30 | 1.410 (6) | C88—H89 | 0.97 |
C31—C39 | 1.538 (7) | C88—H90 | 0.97 |
C2—C3 | 1.404 (7) | C12—H13 | 0.96 |
C2—C10 | 1.513 (7) | C12—H14 | 0.96 |
C39—C41 | 1.527 (7) | C12—H15 | 0.96 |
C39—C45 | 1.542 (7) | C65—C63 | 1.387 (7) |
C39—H40 | 0.98 | C65—C167 | 1.392 (7) |
C45—H46 | 0.96 | C65—H66 | 0.93 |
C45—H47 | 0.96 | C80—H81 | 0.96 |
C45—H48 | 0.96 | C80—H82 | 0.96 |
C10—C16 | 1.531 (6) | C80—H83 | 0.96 |
C10—C12 | 1.542 (7) | C98—H99 | 0.96 |
C10—H11 | 0.98 | C98—H100 | 0.96 |
C41—H42 | 0.96 | C98—H101 | 0.96 |
C41—H43 | 0.96 | C167—C59 | 1.407 (7) |
C41—H44 | 0.96 | C26—H27 | 0.96 |
C22—C20 | 1.526 (7) | C26—H28 | 0.96 |
C22—H23 | 0.96 | C26—H29 | 0.96 |
C22—H24 | 0.96 | C7—H8 | 0.93 |
C22—H25 | 0.96 | C74—H75 | 0.96 |
C34—C36 | 1.384 (7) | C74—H76 | 0.96 |
C34—C32 | 1.392 (7) | C74—H77 | 0.96 |
C34—H35 | 0.93 | C63—H64 | 0.93 |
C20—C9 | 1.516 (6) | C102—H103 | 0.97 |
C20—C26 | 1.526 (7) | C102—H104 | 0.97 |
C20—H21 | 0.98 | C49—C55 | 1.531 (7) |
C3—H4 | 0.93 | C49—C51 | 1.542 (7) |
C84—H85 | 0.96 | C49—H50 | 0.98 |
C84—H86 | 0.96 | C55—H56 | 0.96 |
C84—H87 | 0.96 | C55—H57 | 0.96 |
C95—C98 | 1.514 (7) | C55—H58 | 0.96 |
C95—H96 | 0.97 | C51—H52 | 0.96 |
C95—H97 | 0.97 | C51—H53 | 0.96 |
C61—C63 | 1.381 (7) | C51—H54 | 0.96 |
| | | |
O112—Si1—O111 | 100.97 (17) | H71—C70—H72 | 109.5 |
O112—Si1—O110 | 106.15 (18) | C68—C70—H73 | 109.5 |
O111—Si1—O110 | 106.38 (16) | H71—C70—H73 | 109.5 |
O112—Si1—S114 | 114.07 (14) | H72—C70—H73 | 109.5 |
O111—Si1—S114 | 117.56 (13) | C102—C105—H106 | 109.5 |
O110—Si1—S114 | 110.67 (12) | C102—C105—H107 | 109.5 |
C59—O112—Si1 | 130.2 (3) | H106—C105—H107 | 109.5 |
C1—O110—Si1 | 130.1 (3) | C102—C105—H108 | 109.5 |
C30—O111—Si1 | 139.7 (3) | H106—C105—H108 | 109.5 |
C102—N109—C88 | 112.1 (4) | H107—C105—H108 | 109.5 |
C102—N109—C95 | 114.1 (4) | C7—C9—C1 | 117.8 (4) |
C88—N109—C95 | 111.1 (4) | C7—C9—C20 | 121.8 (4) |
C102—N109—H115 | 102 (3) | C1—C9—C20 | 120.4 (4) |
C88—N109—H115 | 108 (3) | C88—C91—H92 | 109.5 |
C95—N109—H115 | 109 (3) | C88—C91—H93 | 109.5 |
C36—C38—C30 | 116.9 (4) | H92—C91—H93 | 109.5 |
C36—C38—C49 | 119.8 (4) | C88—C91—H94 | 109.5 |
C30—C38—C49 | 123.3 (4) | H92—C91—H94 | 109.5 |
C167—C78—C80 | 112.2 (4) | H93—C91—H94 | 109.5 |
C167—C78—C84 | 109.7 (4) | C10—C16—H17 | 109.5 |
C80—C78—C84 | 109.7 (4) | C10—C16—H18 | 109.5 |
C167—C78—H79 | 108.4 | H17—C16—H18 | 109.5 |
C80—C78—H79 | 108.4 | C10—C16—H19 | 109.5 |
C84—C78—H79 | 108.4 | H17—C16—H19 | 109.5 |
O110—C1—C2 | 120.2 (4) | H18—C16—H19 | 109.5 |
O110—C1—C9 | 118.3 (4) | C61—C60—C59 | 118.2 (5) |
C2—C1—C9 | 121.5 (4) | C61—C60—C68 | 119.3 (4) |
C3—C5—C7 | 119.1 (5) | C59—C60—C68 | 122.5 (4) |
C3—C5—H6 | 120.4 | C34—C36—C38 | 123.2 (5) |
C7—C5—H6 | 120.4 | C34—C36—H37 | 118.4 |
C32—C31—C30 | 118.7 (5) | C38—C36—H37 | 118.4 |
C32—C31—C39 | 120.8 (4) | N109—C88—C91 | 113.5 (4) |
C30—C31—C39 | 120.5 (4) | N109—C88—H89 | 108.9 |
C1—C2—C3 | 117.7 (4) | C91—C88—H89 | 108.9 |
C1—C2—C10 | 123.4 (4) | N109—C88—H90 | 108.9 |
C3—C2—C10 | 118.8 (4) | C91—C88—H90 | 108.9 |
C41—C39—C31 | 112.8 (4) | H89—C88—H90 | 107.7 |
C41—C39—C45 | 110.9 (4) | C10—C12—H13 | 109.5 |
C31—C39—C45 | 109.3 (4) | C10—C12—H14 | 109.5 |
C41—C39—H40 | 107.9 | H13—C12—H14 | 109.5 |
C31—C39—H40 | 107.9 | C10—C12—H15 | 109.5 |
C45—C39—H40 | 107.9 | H13—C12—H15 | 109.5 |
C39—C45—H46 | 109.5 | H14—C12—H15 | 109.5 |
C39—C45—H47 | 109.5 | C63—C65—C167 | 121.9 (5) |
H46—C45—H47 | 109.5 | C63—C65—H66 | 119.1 |
C39—C45—H48 | 109.5 | C167—C65—H66 | 119.1 |
H46—C45—H48 | 109.5 | C78—C80—H81 | 109.5 |
H47—C45—H48 | 109.5 | C78—C80—H82 | 109.5 |
C2—C10—C16 | 112.9 (4) | H81—C80—H82 | 109.5 |
C2—C10—C12 | 110.4 (4) | C78—C80—H83 | 109.5 |
C16—C10—C12 | 110.3 (4) | H81—C80—H83 | 109.5 |
C2—C10—H11 | 107.7 | H82—C80—H83 | 109.5 |
C16—C10—H11 | 107.7 | C95—C98—H99 | 109.5 |
C12—C10—H11 | 107.7 | C95—C98—H100 | 109.5 |
C39—C41—H42 | 109.5 | H99—C98—H100 | 109.5 |
C39—C41—H43 | 109.5 | C95—C98—H101 | 109.5 |
H42—C41—H43 | 109.5 | H99—C98—H101 | 109.5 |
C39—C41—H44 | 109.5 | H100—C98—H101 | 109.5 |
H42—C41—H44 | 109.5 | C65—C167—C59 | 117.9 (4) |
H43—C41—H44 | 109.5 | C65—C167—C78 | 119.8 (5) |
C20—C22—H23 | 109.5 | C59—C167—C78 | 122.3 (4) |
C20—C22—H24 | 109.5 | O112—C59—C60 | 118.7 (4) |
H23—C22—H24 | 109.5 | O112—C59—C167 | 119.8 (4) |
C20—C22—H25 | 109.5 | C60—C59—C167 | 121.3 (4) |
H23—C22—H25 | 109.5 | C20—C26—H27 | 109.5 |
H24—C22—H25 | 109.5 | C20—C26—H28 | 109.5 |
C36—C34—C32 | 118.1 (5) | H27—C26—H28 | 109.5 |
C36—C34—H35 | 120.9 | C20—C26—H29 | 109.5 |
C32—C34—H35 | 120.9 | H27—C26—H29 | 109.5 |
C9—C20—C26 | 113.9 (4) | H28—C26—H29 | 109.5 |
C9—C20—C22 | 109.9 (4) | C5—C7—C9 | 122.1 (5) |
C26—C20—C22 | 109.9 (4) | C5—C7—H8 | 119 |
C9—C20—H21 | 107.6 | C9—C7—H8 | 119 |
C26—C20—H21 | 107.6 | C68—C74—H75 | 109.5 |
C22—C20—H21 | 107.6 | C68—C74—H76 | 109.5 |
C5—C3—C2 | 121.8 (5) | H75—C74—H76 | 109.5 |
C5—C3—H4 | 119.1 | C68—C74—H77 | 109.5 |
C2—C3—H4 | 119.1 | H75—C74—H77 | 109.5 |
C78—C84—H85 | 109.5 | H76—C74—H77 | 109.5 |
C78—C84—H86 | 109.5 | C61—C63—C65 | 119.0 (5) |
H85—C84—H86 | 109.5 | C61—C63—H64 | 120.5 |
C78—C84—H87 | 109.5 | C65—C63—H64 | 120.5 |
H85—C84—H87 | 109.5 | N109—C102—C105 | 112.1 (4) |
H86—C84—H87 | 109.5 | N109—C102—H103 | 109.2 |
N109—C95—C98 | 114.5 (4) | C105—C102—H103 | 109.2 |
N109—C95—H96 | 108.6 | N109—C102—H104 | 109.2 |
C98—C95—H96 | 108.6 | C105—C102—H104 | 109.2 |
N109—C95—H97 | 108.6 | H103—C102—H104 | 107.9 |
C98—C95—H97 | 108.6 | C38—C49—C55 | 112.3 (4) |
H96—C95—H97 | 107.6 | C38—C49—C51 | 111.1 (4) |
O111—C30—C38 | 120.5 (4) | C55—C49—C51 | 109.1 (4) |
O111—C30—C31 | 117.8 (4) | C38—C49—H50 | 108.1 |
C38—C30—C31 | 121.4 (4) | C55—C49—H50 | 108.1 |
C63—C61—C60 | 121.7 (5) | C51—C49—H50 | 108.1 |
C63—C61—H62 | 119.1 | C49—C55—H56 | 109.5 |
C60—C61—H62 | 119.1 | C49—C55—H57 | 109.5 |
C31—C32—C34 | 121.7 (5) | H56—C55—H57 | 109.5 |
C31—C32—H33 | 119.2 | C49—C55—H58 | 109.5 |
C34—C32—H33 | 119.2 | H56—C55—H58 | 109.5 |
C60—C68—C70 | 112.3 (4) | H57—C55—H58 | 109.5 |
C60—C68—C74 | 109.6 (4) | C49—C51—H52 | 109.5 |
C70—C68—C74 | 110.9 (4) | C49—C51—H53 | 109.5 |
C60—C68—H69 | 108 | H52—C51—H53 | 109.5 |
C70—C68—H69 | 108 | C49—C51—H54 | 109.5 |
C74—C68—H69 | 108 | H52—C51—H54 | 109.5 |
C68—C70—H71 | 109.5 | H53—C51—H54 | 109.5 |
C68—C70—H72 | 109.5 | | |
| | | |
O111—Si1—O112—C59 | −16.4 (4) | C2—C1—C9—C20 | 178.0 (4) |
O110—Si1—O112—C59 | 94.4 (4) | C26—C20—C9—C7 | −33.3 (6) |
S114—Si1—O112—C59 | −143.4 (4) | C22—C20—C9—C7 | 90.6 (5) |
O112—Si1—O110—C1 | 118.5 (4) | C26—C20—C9—C1 | 148.6 (4) |
O111—Si1—O110—C1 | −134.5 (4) | C22—C20—C9—C1 | −87.5 (5) |
S114—Si1—O110—C1 | −5.7 (4) | C63—C61—C60—C59 | 0.1 (7) |
O112—Si1—O111—C30 | 166.6 (5) | C63—C61—C60—C68 | −178.2 (5) |
O110—Si1—O111—C30 | 55.9 (5) | C70—C68—C60—C61 | −57.5 (6) |
S114—Si1—O111—C30 | −68.7 (5) | C74—C68—C60—C61 | 66.3 (6) |
Si1—O110—C1—C2 | −77.3 (5) | C70—C68—C60—C59 | 124.3 (5) |
Si1—O110—C1—C9 | 106.2 (4) | C74—C68—C60—C59 | −111.9 (5) |
O110—C1—C2—C3 | −177.0 (4) | C32—C34—C36—C38 | −0.9 (8) |
C9—C1—C2—C3 | −0.6 (7) | C30—C38—C36—C34 | 0.0 (8) |
O110—C1—C2—C10 | 0.2 (7) | C49—C38—C36—C34 | 179.4 (5) |
C9—C1—C2—C10 | 176.6 (4) | C102—N109—C88—C91 | 67.6 (5) |
C32—C31—C39—C41 | −30.7 (6) | C95—N109—C88—C91 | −163.4 (4) |
C30—C31—C39—C41 | 152.8 (4) | C63—C65—C167—C59 | −1.2 (7) |
C32—C31—C39—C45 | 93.2 (5) | C63—C65—C167—C78 | 175.8 (5) |
C30—C31—C39—C45 | −83.3 (5) | C80—C78—C167—C65 | 54.3 (6) |
C1—C2—C10—C16 | 130.2 (5) | C84—C78—C167—C65 | −67.9 (6) |
C3—C2—C10—C16 | −52.6 (6) | C80—C78—C167—C59 | −128.9 (5) |
C1—C2—C10—C12 | −105.9 (5) | C84—C78—C167—C59 | 108.9 (5) |
C3—C2—C10—C12 | 71.3 (5) | Si1—O112—C59—C60 | −104.2 (5) |
C7—C5—C3—C2 | 0.3 (7) | Si1—O112—C59—C167 | 80.3 (5) |
C1—C2—C3—C5 | 0.6 (7) | C61—C60—C59—O112 | −177.3 (4) |
C10—C2—C3—C5 | −176.8 (4) | C68—C60—C59—O112 | 0.9 (7) |
C102—N109—C95—C98 | 58.6 (6) | C61—C60—C59—C167 | −1.9 (7) |
C88—N109—C95—C98 | −69.4 (5) | C68—C60—C59—C167 | 176.4 (4) |
Si1—O111—C30—C38 | 89.7 (6) | C65—C167—C59—O112 | 177.8 (4) |
Si1—O111—C30—C31 | −96.0 (5) | C78—C167—C59—O112 | 0.9 (7) |
C36—C38—C30—O111 | 175.3 (4) | C65—C167—C59—C60 | 2.4 (7) |
C49—C38—C30—O111 | −4.1 (7) | C78—C167—C59—C60 | −174.5 (4) |
C36—C38—C30—C31 | 1.2 (7) | C3—C5—C7—C9 | −1.1 (7) |
C49—C38—C30—C31 | −178.2 (4) | C1—C9—C7—C5 | 1.1 (7) |
C32—C31—C30—O111 | −175.8 (4) | C20—C9—C7—C5 | −177.1 (5) |
C39—C31—C30—O111 | 0.7 (6) | C60—C61—C63—C65 | 1.1 (8) |
C32—C31—C30—C38 | −1.5 (7) | C167—C65—C63—C61 | −0.5 (8) |
C39—C31—C30—C38 | 175.0 (4) | C88—N109—C102—C105 | −174.9 (4) |
C30—C31—C32—C34 | 0.7 (7) | C95—N109—C102—C105 | 57.7 (6) |
C39—C31—C32—C34 | −175.9 (5) | C36—C38—C49—C55 | 69.4 (6) |
C36—C34—C32—C31 | 0.5 (8) | C30—C38—C49—C55 | −111.2 (5) |
O110—C1—C9—C7 | 176.3 (4) | C36—C38—C49—C51 | −53.1 (6) |
C2—C1—C9—C7 | −0.2 (7) | C30—C38—C49—C51 | 126.3 (5) |
O110—C1—C9—C20 | −5.5 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N109—H115···S114 | 1.03 (6) | 2.11 (6) | 3.081 (4) | 157 (5) |
Crystal data top
C36H51O3SSi·C6H16N | F(000) = 1520 |
Mr = 694.11 | Dx = 1.119 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 1743 reflections |
a = 11.6463 (11) Å | θ = 3.6–29.4° |
b = 17.9257 (12) Å | µ = 0.14 mm−1 |
c = 20.110 (3) Å | T = 120 K |
β = 101.060 (9)° | Block, colourless |
V = 4120.3 (7) Å3 | 0.34 × 0.22 × 0.13 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 6269 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.057 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.2° |
rotation method scans | h = −14→14 |
17343 measured reflections | k = −21→22 |
7408 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 0.98 | Δρmax = 0.19 e Å−3 |
7408 reflections | Δρmin = −0.19 e Å−3 |
452 parameters | Absolute structure: Flack x determined using 2316 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
Si1 | 0.55615 (6) | 0.26115 (4) | 0.06092 (4) | 0.01183 (17) | |
S114 | 0.40771 (6) | 0.20840 (4) | 0.01632 (4) | 0.01770 (17) | |
O112 | 0.54719 (16) | 0.35323 (10) | 0.05813 (12) | 0.0149 (4) | |
O110 | 0.59264 (16) | 0.23835 (11) | 0.14271 (11) | 0.0149 (4) | |
O111 | 0.67399 (16) | 0.24752 (11) | 0.02826 (11) | 0.0147 (4) | |
N109 | 0.1974 (2) | 0.28392 (14) | −0.07516 (14) | 0.0179 (6) | |
H115 | 0.259 (3) | 0.266 (2) | −0.053 (2) | 0.022 (10)* | |
C38 | 0.7320 (2) | 0.14369 (16) | −0.03376 (17) | 0.0170 (6) | |
C78 | 0.5846 (2) | 0.38426 (17) | −0.07822 (17) | 0.0186 (7) | |
H79 | 0.5387 | 0.3434 | −0.0641 | 0.022* | |
C1 | 0.5325 (2) | 0.19585 (16) | 0.18234 (16) | 0.0154 (6) | |
C5 | 0.4236 (3) | 0.11087 (18) | 0.26750 (18) | 0.0218 (7) | |
H6 | 0.3867 | 0.0823 | 0.2958 | 0.026* | |
C31 | 0.8580 (2) | 0.18903 (17) | 0.07038 (17) | 0.0164 (6) | |
C2 | 0.4378 (2) | 0.22605 (17) | 0.20641 (17) | 0.0169 (6) | |
C39 | 0.8823 (2) | 0.24622 (17) | 0.12759 (17) | 0.0183 (7) | |
H40 | 0.8075 | 0.2589 | 0.1403 | 0.022* | |
C45 | 0.9325 (3) | 0.31792 (19) | 0.1023 (2) | 0.0257 (8) | |
H46 | 1.0069 | 0.3072 | 0.0905 | 0.039* | |
H47 | 0.9423 | 0.355 | 0.1374 | 0.039* | |
H48 | 0.8797 | 0.3363 | 0.0631 | 0.039* | |
C10 | 0.3948 (2) | 0.30564 (17) | 0.19135 (17) | 0.0182 (7) | |
H11 | 0.4329 | 0.3256 | 0.1557 | 0.022* | |
C41 | 0.9639 (3) | 0.2165 (2) | 0.19059 (18) | 0.0261 (8) | |
H42 | 0.9345 | 0.1698 | 0.2036 | 0.039* | |
H43 | 0.9678 | 0.2517 | 0.2269 | 0.039* | |
H44 | 1.0407 | 0.2093 | 0.1809 | 0.039* | |
C22 | 0.6270 (3) | 0.0508 (2) | 0.1051 (2) | 0.0284 (8) | |
H23 | 0.5821 | 0.0081 | 0.1135 | 0.043* | |
H24 | 0.6912 | 0.0351 | 0.0849 | 0.043* | |
H25 | 0.578 | 0.0844 | 0.0749 | 0.043* | |
C34 | 0.9223 (3) | 0.08698 (18) | 0.0079 (2) | 0.0266 (8) | |
H35 | 0.9783 | 0.0514 | 0.0034 | 0.032* | |
C20 | 0.6740 (2) | 0.09051 (17) | 0.17190 (18) | 0.0188 (7) | |
H21 | 0.7234 | 0.1319 | 0.1623 | 0.023* | |
C3 | 0.3840 (2) | 0.18169 (18) | 0.24937 (17) | 0.0198 (7) | |
H4 | 0.3205 | 0.2006 | 0.2658 | 0.024* | |
C84 | 0.4992 (3) | 0.43962 (19) | −0.1198 (2) | 0.0292 (8) | |
H85 | 0.5419 | 0.4818 | −0.1317 | 0.044* | |
H86 | 0.4435 | 0.456 | −0.0935 | 0.044* | |
H87 | 0.4589 | 0.4156 | −0.1603 | 0.044* | |
C95 | 0.1070 (3) | 0.25019 (19) | −0.03925 (18) | 0.0224 (7) | |
H96 | 0.1257 | 0.264 | 0.0082 | 0.027* | |
H97 | 0.1115 | 0.1963 | −0.0419 | 0.027* | |
C30 | 0.7525 (2) | 0.19174 (16) | 0.02212 (17) | 0.0152 (6) | |
C61 | 0.7654 (3) | 0.50285 (19) | 0.0972 (2) | 0.0260 (8) | |
H62 | 0.8031 | 0.5303 | 0.1343 | 0.031* | |
C32 | 0.9407 (2) | 0.13580 (18) | 0.06218 (18) | 0.0222 (7) | |
H33 | 1.0102 | 0.1329 | 0.0939 | 0.027* | |
C68 | 0.6596 (3) | 0.43437 (18) | 0.17706 (18) | 0.0220 (7) | |
H69 | 0.6061 | 0.3918 | 0.1746 | 0.026* | |
C70 | 0.7694 (3) | 0.4162 (2) | 0.2294 (2) | 0.0301 (8) | |
H71 | 0.806 | 0.3724 | 0.2155 | 0.045* | |
H72 | 0.7483 | 0.4073 | 0.2726 | 0.045* | |
H73 | 0.8229 | 0.4574 | 0.233 | 0.045* | |
C105 | 0.2230 (3) | 0.3986 (2) | −0.0028 (2) | 0.0325 (8) | |
H106 | 0.239 | 0.4511 | −0.0043 | 0.049* | |
H107 | 0.2892 | 0.3737 | 0.0238 | 0.049* | |
H108 | 0.1555 | 0.391 | 0.0173 | 0.049* | |
C9 | 0.5739 (2) | 0.12335 (16) | 0.20050 (16) | 0.0165 (6) | |
C91 | 0.2934 (3) | 0.2664 (2) | −0.1760 (2) | 0.0306 (8) | |
H92 | 0.2845 | 0.2407 | −0.2185 | 0.046* | |
H93 | 0.3614 | 0.2479 | −0.1458 | 0.046* | |
H94 | 0.3024 | 0.3189 | −0.1832 | 0.046* | |
C16 | 0.2621 (3) | 0.3089 (2) | 0.16583 (19) | 0.0258 (8) | |
H17 | 0.2405 | 0.2747 | 0.1288 | 0.039* | |
H18 | 0.2399 | 0.3586 | 0.1509 | 0.039* | |
H19 | 0.2228 | 0.2953 | 0.2019 | 0.039* | |
C60 | 0.6860 (3) | 0.44709 (16) | 0.10692 (18) | 0.0189 (6) | |
C36 | 0.8198 (3) | 0.09168 (18) | −0.03957 (18) | 0.0218 (7) | |
H37 | 0.8086 | 0.0595 | −0.0765 | 0.026* | |
C88 | 0.1857 (3) | 0.25348 (19) | −0.14514 (18) | 0.0233 (7) | |
H89 | 0.1187 | 0.2766 | −0.1739 | 0.028* | |
H90 | 0.1707 | 0.2003 | −0.1441 | 0.028* | |
C12 | 0.4300 (3) | 0.35484 (17) | 0.25449 (19) | 0.0221 (7) | |
H13 | 0.3956 | 0.3354 | 0.2906 | 0.033* | |
H14 | 0.4028 | 0.4048 | 0.2442 | 0.033* | |
H15 | 0.5137 | 0.355 | 0.2681 | 0.033* | |
C65 | 0.7313 (3) | 0.47825 (18) | −0.02166 (19) | 0.0241 (7) | |
H66 | 0.7468 | 0.489 | −0.0643 | 0.029* | |
C80 | 0.6655 (3) | 0.3513 (2) | −0.1216 (2) | 0.0317 (8) | |
H81 | 0.62 | 0.3247 | −0.1591 | 0.047* | |
H82 | 0.7197 | 0.3177 | −0.0948 | 0.047* | |
H83 | 0.7078 | 0.3908 | −0.1385 | 0.047* | |
C98 | −0.0171 (3) | 0.2745 (2) | −0.0681 (2) | 0.0296 (8) | |
H99 | −0.0346 | 0.2643 | −0.1159 | 0.044* | |
H100 | −0.0249 | 0.327 | −0.0607 | 0.044* | |
H101 | −0.0705 | 0.2475 | −0.0462 | 0.044* | |
C167 | 0.6504 (2) | 0.42240 (17) | −0.01496 (17) | 0.0175 (7) | |
C59 | 0.6304 (2) | 0.40640 (16) | 0.05011 (17) | 0.0159 (6) | |
C26 | 0.7509 (3) | 0.0370 (2) | 0.2200 (2) | 0.0333 (9) | |
H27 | 0.7087 | −0.0084 | 0.2235 | 0.05* | |
H28 | 0.7718 | 0.0596 | 0.2639 | 0.05* | |
H29 | 0.8205 | 0.0261 | 0.2028 | 0.05* | |
C7 | 0.5182 (3) | 0.08218 (18) | 0.24365 (17) | 0.0209 (7) | |
H8 | 0.545 | 0.0345 | 0.2567 | 0.025* | |
C74 | 0.5981 (3) | 0.5028 (2) | 0.1996 (2) | 0.0331 (8) | |
H75 | 0.5827 | 0.4945 | 0.2442 | 0.05* | |
H76 | 0.5257 | 0.5111 | 0.1685 | 0.05* | |
H77 | 0.6475 | 0.5458 | 0.2001 | 0.05* | |
C63 | 0.7888 (3) | 0.51793 (19) | 0.03410 (19) | 0.0273 (8) | |
H64 | 0.8429 | 0.5545 | 0.0288 | 0.033* | |
C102 | 0.1997 (3) | 0.36735 (18) | −0.07409 (18) | 0.0231 (7) | |
H103 | 0.1252 | 0.3861 | −0.0983 | 0.028* | |
H104 | 0.26 | 0.3847 | −0.0976 | 0.028* | |
C49 | 0.6219 (3) | 0.14596 (17) | −0.08856 (17) | 0.0197 (7) | |
H50 | 0.5763 | 0.1897 | −0.0803 | 0.024* | |
C55 | 0.5449 (3) | 0.07651 (19) | −0.0872 (2) | 0.0268 (8) | |
H56 | 0.5867 | 0.033 | −0.0971 | 0.04* | |
H57 | 0.4744 | 0.0817 | −0.1206 | 0.04* | |
H58 | 0.5256 | 0.0715 | −0.0431 | 0.04* | |
C51 | 0.6516 (3) | 0.1539 (2) | −0.15909 (19) | 0.0285 (8) | |
H52 | 0.7003 | 0.197 | −0.1601 | 0.043* | |
H53 | 0.5808 | 0.1596 | −0.1921 | 0.043* | |
H54 | 0.6925 | 0.1102 | −0.1694 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0101 (3) | 0.0121 (4) | 0.0133 (5) | 0.0000 (3) | 0.0022 (3) | 0.0000 (3) |
S114 | 0.0134 (3) | 0.0158 (4) | 0.0219 (4) | −0.0024 (3) | −0.0016 (3) | 0.0002 (3) |
O112 | 0.0126 (8) | 0.0142 (10) | 0.0180 (12) | −0.0014 (8) | 0.0033 (8) | −0.0012 (9) |
O110 | 0.0129 (9) | 0.0177 (10) | 0.0145 (12) | −0.0003 (8) | 0.0035 (8) | 0.0016 (9) |
O111 | 0.0119 (8) | 0.0157 (11) | 0.0169 (12) | 0.0024 (7) | 0.0037 (8) | 0.0008 (8) |
N109 | 0.0155 (12) | 0.0218 (14) | 0.0154 (15) | 0.0007 (10) | 0.0002 (11) | 0.0019 (11) |
C38 | 0.0190 (14) | 0.0151 (15) | 0.0177 (18) | 0.0000 (11) | 0.0055 (13) | 0.0014 (12) |
C78 | 0.0197 (14) | 0.0191 (16) | 0.0171 (18) | −0.0034 (11) | 0.0037 (13) | 0.0020 (13) |
C1 | 0.0145 (12) | 0.0184 (15) | 0.0122 (16) | −0.0019 (11) | 0.0002 (11) | 0.0011 (12) |
C5 | 0.0260 (15) | 0.0233 (17) | 0.0174 (18) | −0.0071 (12) | 0.0070 (14) | 0.0001 (13) |
C31 | 0.0144 (12) | 0.0203 (16) | 0.0154 (17) | −0.0011 (11) | 0.0050 (12) | 0.0034 (12) |
C2 | 0.0138 (12) | 0.0200 (16) | 0.0160 (17) | −0.0018 (11) | 0.0006 (12) | −0.0009 (12) |
C39 | 0.0132 (12) | 0.0223 (17) | 0.0200 (18) | −0.0012 (11) | 0.0048 (12) | −0.0028 (13) |
C45 | 0.0206 (14) | 0.0268 (18) | 0.030 (2) | −0.0042 (13) | 0.0050 (14) | −0.0059 (15) |
C10 | 0.0170 (13) | 0.0205 (16) | 0.0184 (18) | 0.0034 (11) | 0.0066 (12) | 0.0021 (13) |
C41 | 0.0219 (15) | 0.037 (2) | 0.0184 (19) | −0.0050 (13) | 0.0012 (14) | −0.0030 (15) |
C22 | 0.0319 (17) | 0.0295 (19) | 0.025 (2) | 0.0063 (14) | 0.0075 (15) | −0.0039 (15) |
C34 | 0.0231 (16) | 0.0212 (16) | 0.035 (2) | 0.0081 (13) | 0.0037 (15) | −0.0006 (15) |
C20 | 0.0182 (13) | 0.0155 (15) | 0.0227 (19) | 0.0016 (11) | 0.0041 (13) | 0.0030 (13) |
C3 | 0.0196 (13) | 0.0249 (17) | 0.0165 (18) | −0.0017 (12) | 0.0078 (13) | −0.0018 (13) |
C84 | 0.0251 (15) | 0.0293 (19) | 0.030 (2) | 0.0039 (14) | −0.0036 (15) | −0.0014 (16) |
C95 | 0.0204 (14) | 0.0287 (19) | 0.0182 (19) | −0.0026 (12) | 0.0042 (13) | 0.0050 (14) |
C30 | 0.0148 (13) | 0.0135 (15) | 0.0188 (17) | 0.0022 (10) | 0.0070 (12) | 0.0009 (12) |
C61 | 0.0267 (16) | 0.0224 (17) | 0.027 (2) | −0.0086 (13) | 0.0019 (14) | −0.0039 (14) |
C32 | 0.0151 (14) | 0.0243 (17) | 0.025 (2) | 0.0047 (12) | −0.0004 (13) | 0.0021 (14) |
C68 | 0.0266 (15) | 0.0201 (16) | 0.0195 (19) | −0.0055 (12) | 0.0049 (13) | −0.0029 (13) |
C70 | 0.0340 (18) | 0.0309 (19) | 0.025 (2) | 0.0000 (15) | 0.0033 (16) | 0.0027 (16) |
C105 | 0.047 (2) | 0.0217 (18) | 0.029 (2) | 0.0039 (15) | 0.0061 (17) | −0.0030 (15) |
C9 | 0.0170 (13) | 0.0170 (15) | 0.0143 (17) | −0.0016 (11) | 0.0002 (12) | −0.0020 (12) |
C91 | 0.0349 (18) | 0.036 (2) | 0.024 (2) | −0.0033 (15) | 0.0139 (16) | −0.0060 (16) |
C16 | 0.0181 (14) | 0.036 (2) | 0.023 (2) | 0.0052 (13) | 0.0031 (14) | 0.0026 (15) |
C60 | 0.0177 (13) | 0.0175 (15) | 0.0211 (18) | −0.0009 (12) | 0.0025 (12) | −0.0003 (13) |
C36 | 0.0249 (15) | 0.0190 (16) | 0.0216 (19) | 0.0030 (12) | 0.0048 (14) | −0.0045 (13) |
C88 | 0.0250 (15) | 0.0268 (18) | 0.0175 (19) | −0.0021 (13) | 0.0026 (13) | −0.0032 (14) |
C12 | 0.0229 (15) | 0.0180 (16) | 0.025 (2) | 0.0054 (12) | 0.0047 (14) | 0.0010 (14) |
C65 | 0.0272 (16) | 0.0241 (17) | 0.022 (2) | −0.0056 (13) | 0.0063 (14) | 0.0055 (14) |
C80 | 0.0289 (17) | 0.038 (2) | 0.028 (2) | −0.0009 (15) | 0.0063 (16) | −0.0094 (16) |
C98 | 0.0182 (14) | 0.049 (2) | 0.022 (2) | −0.0020 (14) | 0.0039 (14) | 0.0063 (17) |
C167 | 0.0174 (13) | 0.0164 (15) | 0.0190 (18) | 0.0005 (11) | 0.0044 (13) | 0.0008 (12) |
C59 | 0.0134 (12) | 0.0117 (14) | 0.0226 (18) | −0.0001 (10) | 0.0037 (12) | 0.0019 (13) |
C26 | 0.0293 (17) | 0.032 (2) | 0.037 (2) | 0.0120 (15) | 0.0022 (16) | 0.0035 (17) |
C7 | 0.0254 (15) | 0.0167 (16) | 0.0192 (19) | −0.0034 (12) | 0.0010 (13) | 0.0027 (13) |
C74 | 0.0390 (19) | 0.036 (2) | 0.026 (2) | 0.0058 (16) | 0.0093 (17) | −0.0007 (17) |
C63 | 0.0286 (16) | 0.0227 (17) | 0.030 (2) | −0.0116 (13) | 0.0050 (15) | 0.0015 (15) |
C102 | 0.0277 (15) | 0.0204 (16) | 0.0219 (19) | 0.0022 (12) | 0.0065 (14) | 0.0024 (14) |
C49 | 0.0201 (14) | 0.0211 (16) | 0.0168 (18) | 0.0048 (12) | 0.0009 (13) | −0.0022 (13) |
C55 | 0.0246 (15) | 0.0287 (19) | 0.024 (2) | −0.0017 (13) | −0.0019 (14) | −0.0052 (15) |
C51 | 0.0370 (18) | 0.0325 (19) | 0.0163 (19) | 0.0085 (15) | 0.0057 (15) | −0.0001 (15) |
Geometric parameters (Å, º) top
Si1—O111 | 1.649 (2) | C61—C60 | 1.400 (4) |
Si1—O112 | 1.654 (2) | C61—H62 | 0.93 |
Si1—O110 | 1.669 (2) | C32—H33 | 0.93 |
Si1—S114 | 2.0230 (10) | C68—C60 | 1.517 (5) |
O112—C59 | 1.390 (3) | C68—C70 | 1.527 (5) |
O110—C1 | 1.385 (4) | C68—C74 | 1.532 (5) |
O111—C30 | 1.377 (3) | C68—H69 | 0.98 |
N109—C88 | 1.491 (4) | C70—H71 | 0.96 |
N109—C102 | 1.496 (4) | C70—H72 | 0.96 |
N109—C95 | 1.512 (4) | C70—H73 | 0.96 |
N109—H115 | 0.83 (4) | C105—C102 | 1.515 (5) |
C38—C30 | 1.400 (4) | C105—H106 | 0.96 |
C38—C36 | 1.405 (4) | C105—H107 | 0.96 |
C38—C49 | 1.522 (4) | C105—H108 | 0.96 |
C78—C167 | 1.516 (4) | C9—C7 | 1.391 (4) |
C78—C80 | 1.522 (5) | C91—C88 | 1.521 (4) |
C78—C84 | 1.534 (4) | C91—H92 | 0.96 |
C78—H79 | 0.98 | C91—H93 | 0.96 |
C1—C2 | 1.396 (4) | C91—H94 | 0.96 |
C1—C9 | 1.410 (4) | C16—H17 | 0.96 |
C5—C3 | 1.376 (5) | C16—H18 | 0.96 |
C5—C7 | 1.383 (5) | C16—H19 | 0.96 |
C5—H6 | 0.93 | C60—C59 | 1.404 (4) |
C31—C32 | 1.388 (4) | C36—H37 | 0.93 |
C31—C30 | 1.412 (4) | C88—H89 | 0.97 |
C31—C39 | 1.526 (4) | C88—H90 | 0.97 |
C2—C3 | 1.407 (4) | C12—H13 | 0.96 |
C2—C10 | 1.523 (4) | C12—H14 | 0.96 |
C39—C41 | 1.527 (5) | C12—H15 | 0.96 |
C39—C45 | 1.539 (4) | C65—C63 | 1.387 (5) |
C39—H40 | 0.98 | C65—C167 | 1.399 (4) |
C45—H46 | 0.96 | C65—H66 | 0.93 |
C45—H47 | 0.96 | C80—H81 | 0.96 |
C45—H48 | 0.96 | C80—H82 | 0.96 |
C10—C16 | 1.534 (4) | C80—H83 | 0.96 |
C10—C12 | 1.536 (5) | C98—H99 | 0.96 |
C10—H11 | 0.98 | C98—H100 | 0.96 |
C41—H42 | 0.96 | C98—H101 | 0.96 |
C41—H43 | 0.96 | C167—C59 | 1.402 (5) |
C41—H44 | 0.96 | C26—H27 | 0.96 |
C22—C20 | 1.526 (5) | C26—H28 | 0.96 |
C22—H23 | 0.96 | C26—H29 | 0.96 |
C22—H24 | 0.96 | C7—H8 | 0.93 |
C22—H25 | 0.96 | C74—H75 | 0.96 |
C34—C36 | 1.380 (5) | C74—H76 | 0.96 |
C34—C32 | 1.384 (5) | C74—H77 | 0.96 |
C34—H35 | 0.93 | C63—H64 | 0.93 |
C20—C9 | 1.514 (4) | C102—H103 | 0.97 |
C20—C26 | 1.525 (4) | C102—H104 | 0.97 |
C20—H21 | 0.98 | C49—C51 | 1.530 (5) |
C3—H4 | 0.93 | C49—C55 | 1.537 (4) |
C84—H85 | 0.96 | C49—H50 | 0.98 |
C84—H86 | 0.96 | C55—H56 | 0.96 |
C84—H87 | 0.96 | C55—H57 | 0.96 |
C95—C98 | 1.515 (4) | C55—H58 | 0.96 |
C95—H96 | 0.97 | C51—H52 | 0.96 |
C95—H97 | 0.97 | C51—H53 | 0.96 |
C61—C63 | 1.375 (5) | C51—H54 | 0.96 |
| | | |
O111—Si1—O112 | 100.74 (10) | H71—C70—H72 | 109.5 |
O111—Si1—O110 | 106.39 (10) | C68—C70—H73 | 109.5 |
O112—Si1—O110 | 106.28 (11) | H71—C70—H73 | 109.5 |
O111—Si1—S114 | 117.38 (9) | H72—C70—H73 | 109.5 |
O112—Si1—S114 | 114.11 (8) | C102—C105—H106 | 109.5 |
O110—Si1—S114 | 110.90 (8) | C102—C105—H107 | 109.5 |
C59—O112—Si1 | 130.32 (17) | H106—C105—H107 | 109.5 |
C1—O110—Si1 | 129.83 (17) | C102—C105—H108 | 109.5 |
C30—O111—Si1 | 139.58 (19) | H106—C105—H108 | 109.5 |
C88—N109—C102 | 112.2 (3) | H107—C105—H108 | 109.5 |
C88—N109—C95 | 111.0 (2) | C7—C9—C1 | 118.2 (3) |
C102—N109—C95 | 113.9 (3) | C7—C9—C20 | 121.1 (3) |
C88—N109—H115 | 106 (3) | C1—C9—C20 | 120.7 (3) |
C102—N109—H115 | 112 (2) | C88—C91—H92 | 109.5 |
C95—N109—H115 | 102 (3) | C88—C91—H93 | 109.5 |
C30—C38—C36 | 117.4 (3) | H92—C91—H93 | 109.5 |
C30—C38—C49 | 123.7 (3) | C88—C91—H94 | 109.5 |
C36—C38—C49 | 118.9 (3) | H92—C91—H94 | 109.5 |
C167—C78—C80 | 112.8 (2) | H93—C91—H94 | 109.5 |
C167—C78—C84 | 109.6 (3) | C10—C16—H17 | 109.5 |
C80—C78—C84 | 110.2 (3) | C10—C16—H18 | 109.5 |
C167—C78—H79 | 108 | H17—C16—H18 | 109.5 |
C80—C78—H79 | 108 | C10—C16—H19 | 109.5 |
C84—C78—H79 | 108 | H17—C16—H19 | 109.5 |
O110—C1—C2 | 120.4 (2) | H18—C16—H19 | 109.5 |
O110—C1—C9 | 118.1 (2) | C61—C60—C59 | 118.1 (3) |
C2—C1—C9 | 121.4 (3) | C61—C60—C68 | 119.6 (3) |
C3—C5—C7 | 120.0 (3) | C59—C60—C68 | 122.3 (3) |
C3—C5—H6 | 120 | C34—C36—C38 | 122.0 (3) |
C7—C5—H6 | 120 | C34—C36—H37 | 119 |
C32—C31—C30 | 118.3 (3) | C38—C36—H37 | 119 |
C32—C31—C39 | 121.2 (3) | N109—C88—C91 | 113.3 (3) |
C30—C31—C39 | 120.4 (3) | N109—C88—H89 | 108.9 |
C1—C2—C3 | 118.0 (3) | C91—C88—H89 | 108.9 |
C1—C2—C10 | 123.1 (3) | N109—C88—H90 | 108.9 |
C3—C2—C10 | 118.9 (3) | C91—C88—H90 | 108.9 |
C41—C39—C31 | 112.8 (3) | H89—C88—H90 | 107.7 |
C41—C39—C45 | 110.5 (2) | C10—C12—H13 | 109.5 |
C31—C39—C45 | 109.8 (3) | C10—C12—H14 | 109.5 |
C41—C39—H40 | 107.9 | H13—C12—H14 | 109.5 |
C31—C39—H40 | 107.9 | C10—C12—H15 | 109.5 |
C45—C39—H40 | 107.9 | H13—C12—H15 | 109.5 |
C39—C45—H46 | 109.5 | H14—C12—H15 | 109.5 |
C39—C45—H47 | 109.5 | C63—C65—C167 | 121.3 (3) |
H46—C45—H47 | 109.5 | C63—C65—H66 | 119.4 |
C39—C45—H48 | 109.5 | C167—C65—H66 | 119.4 |
H46—C45—H48 | 109.5 | C78—C80—H81 | 109.5 |
H47—C45—H48 | 109.5 | C78—C80—H82 | 109.5 |
C2—C10—C16 | 111.9 (3) | H81—C80—H82 | 109.5 |
C2—C10—C12 | 110.4 (3) | C78—C80—H83 | 109.5 |
C16—C10—C12 | 110.3 (3) | H81—C80—H83 | 109.5 |
C2—C10—H11 | 108 | H82—C80—H83 | 109.5 |
C16—C10—H11 | 108 | C95—C98—H99 | 109.5 |
C12—C10—H11 | 108 | C95—C98—H100 | 109.5 |
C39—C41—H42 | 109.5 | H99—C98—H100 | 109.5 |
C39—C41—H43 | 109.5 | C95—C98—H101 | 109.5 |
H42—C41—H43 | 109.5 | H99—C98—H101 | 109.5 |
C39—C41—H44 | 109.5 | H100—C98—H101 | 109.5 |
H42—C41—H44 | 109.5 | C65—C167—C59 | 118.1 (3) |
H43—C41—H44 | 109.5 | C65—C167—C78 | 118.9 (3) |
C20—C22—H23 | 109.5 | C59—C167—C78 | 122.9 (3) |
C20—C22—H24 | 109.5 | O112—C59—C167 | 119.5 (3) |
H23—C22—H24 | 109.5 | O112—C59—C60 | 119.0 (3) |
C20—C22—H25 | 109.5 | C167—C59—C60 | 121.3 (3) |
H23—C22—H25 | 109.5 | C20—C26—H27 | 109.5 |
H24—C22—H25 | 109.5 | C20—C26—H28 | 109.5 |
C36—C34—C32 | 119.4 (3) | H27—C26—H28 | 109.5 |
C36—C34—H35 | 120.3 | C20—C26—H29 | 109.5 |
C32—C34—H35 | 120.3 | H27—C26—H29 | 109.5 |
C9—C20—C26 | 113.9 (3) | H28—C26—H29 | 109.5 |
C9—C20—C22 | 110.1 (2) | C5—C7—C9 | 121.2 (3) |
C26—C20—C22 | 109.4 (3) | C5—C7—H8 | 119.4 |
C9—C20—H21 | 107.7 | C9—C7—H8 | 119.4 |
C26—C20—H21 | 107.7 | C68—C74—H75 | 109.5 |
C22—C20—H21 | 107.7 | C68—C74—H76 | 109.5 |
C5—C3—C2 | 121.2 (3) | H75—C74—H76 | 109.5 |
C5—C3—H4 | 119.4 | C68—C74—H77 | 109.5 |
C2—C3—H4 | 119.4 | H75—C74—H77 | 109.5 |
C78—C84—H85 | 109.5 | H76—C74—H77 | 109.5 |
C78—C84—H86 | 109.5 | C61—C63—C65 | 119.7 (3) |
H85—C84—H86 | 109.5 | C61—C63—H64 | 120.2 |
C78—C84—H87 | 109.5 | C65—C63—H64 | 120.2 |
H85—C84—H87 | 109.5 | N109—C102—C105 | 112.5 (3) |
H86—C84—H87 | 109.5 | N109—C102—H103 | 109.1 |
N109—C95—C98 | 113.7 (3) | C105—C102—H103 | 109.1 |
N109—C95—H96 | 108.8 | N109—C102—H104 | 109.1 |
C98—C95—H96 | 108.8 | C105—C102—H104 | 109.1 |
N109—C95—H97 | 108.8 | H103—C102—H104 | 107.8 |
C98—C95—H97 | 108.8 | C38—C49—C51 | 111.4 (3) |
H96—C95—H97 | 107.7 | C38—C49—C55 | 112.2 (3) |
O111—C30—C38 | 120.3 (3) | C51—C49—C55 | 109.2 (3) |
O111—C30—C31 | 117.9 (3) | C38—C49—H50 | 108 |
C38—C30—C31 | 121.5 (3) | C51—C49—H50 | 108 |
C63—C61—C60 | 121.5 (3) | C55—C49—H50 | 108 |
C63—C61—H62 | 119.3 | C49—C55—H56 | 109.5 |
C60—C61—H62 | 119.3 | C49—C55—H57 | 109.5 |
C34—C32—C31 | 121.5 (3) | H56—C55—H57 | 109.5 |
C34—C32—H33 | 119.3 | C49—C55—H58 | 109.5 |
C31—C32—H33 | 119.3 | H56—C55—H58 | 109.5 |
C60—C68—C70 | 112.4 (3) | H57—C55—H58 | 109.5 |
C60—C68—C74 | 110.1 (3) | C49—C51—H52 | 109.5 |
C70—C68—C74 | 110.1 (3) | C49—C51—H53 | 109.5 |
C60—C68—H69 | 108 | H52—C51—H53 | 109.5 |
C70—C68—H69 | 108 | C49—C51—H54 | 109.5 |
C74—C68—H69 | 108 | H52—C51—H54 | 109.5 |
C68—C70—H71 | 109.5 | H53—C51—H54 | 109.5 |
C68—C70—H72 | 109.5 | | |
| | | |
O111—Si1—O112—C59 | −16.9 (3) | C2—C1—C9—C20 | 177.8 (3) |
O110—Si1—O112—C59 | 93.9 (3) | C26—C20—C9—C7 | −33.8 (4) |
S114—Si1—O112—C59 | −143.6 (2) | C22—C20—C9—C7 | 89.5 (3) |
O111—Si1—O110—C1 | −134.6 (2) | C26—C20—C9—C1 | 148.1 (3) |
O112—Si1—O110—C1 | 118.6 (2) | C22—C20—C9—C1 | −88.5 (3) |
S114—Si1—O110—C1 | −5.9 (2) | C63—C61—C60—C59 | 0.1 (5) |
O112—Si1—O111—C30 | 166.2 (3) | C63—C61—C60—C68 | −177.8 (3) |
O110—Si1—O111—C30 | 55.5 (3) | C70—C68—C60—C61 | −57.9 (4) |
S114—Si1—O111—C30 | −69.3 (3) | C74—C68—C60—C61 | 65.3 (4) |
Si1—O110—C1—C2 | −77.3 (3) | C70—C68—C60—C59 | 124.3 (3) |
Si1—O110—C1—C9 | 106.2 (3) | C74—C68—C60—C59 | −112.5 (3) |
O110—C1—C2—C3 | −176.7 (3) | C32—C34—C36—C38 | −1.4 (5) |
C9—C1—C2—C3 | −0.3 (4) | C30—C38—C36—C34 | 0.6 (5) |
O110—C1—C2—C10 | 0.0 (4) | C49—C38—C36—C34 | 179.4 (3) |
C9—C1—C2—C10 | 176.4 (3) | C102—N109—C88—C91 | 68.6 (4) |
C32—C31—C39—C41 | −30.7 (4) | C95—N109—C88—C91 | −162.7 (3) |
C30—C31—C39—C41 | 152.8 (3) | C63—C65—C167—C59 | −1.3 (5) |
C32—C31—C39—C45 | 93.0 (3) | C63—C65—C167—C78 | 176.2 (3) |
C30—C31—C39—C45 | −83.5 (3) | C80—C78—C167—C65 | 54.6 (4) |
C1—C2—C10—C16 | 130.8 (3) | C84—C78—C167—C65 | −68.7 (4) |
C3—C2—C10—C16 | −52.6 (4) | C80—C78—C167—C59 | −128.1 (3) |
C1—C2—C10—C12 | −106.0 (3) | C84—C78—C167—C59 | 108.6 (3) |
C3—C2—C10—C12 | 70.7 (3) | Si1—O112—C59—C167 | 81.0 (3) |
C7—C5—C3—C2 | 0.2 (5) | Si1—O112—C59—C60 | −104.0 (3) |
C1—C2—C3—C5 | 0.3 (5) | C65—C167—C59—O112 | 177.5 (3) |
C10—C2—C3—C5 | −176.5 (3) | C78—C167—C59—O112 | 0.2 (4) |
C88—N109—C95—C98 | −68.8 (4) | C65—C167—C59—C60 | 2.6 (4) |
C102—N109—C95—C98 | 59.0 (4) | C78—C167—C59—C60 | −174.7 (3) |
Si1—O111—C30—C38 | 89.9 (4) | C61—C60—C59—O112 | −177.0 (3) |
Si1—O111—C30—C31 | −95.5 (3) | C68—C60—C59—O112 | 0.8 (4) |
C36—C38—C30—O111 | 175.3 (3) | C61—C60—C59—C167 | −2.1 (4) |
C49—C38—C30—O111 | −3.4 (4) | C68—C60—C59—C167 | 175.7 (3) |
C36—C38—C30—C31 | 0.9 (5) | C3—C5—C7—C9 | −0.9 (5) |
C49—C38—C30—C31 | −177.8 (3) | C1—C9—C7—C5 | 0.9 (4) |
C32—C31—C30—O111 | −176.1 (3) | C20—C9—C7—C5 | −177.2 (3) |
C39—C31—C30—O111 | 0.5 (4) | C60—C61—C63—C65 | 1.2 (5) |
C32—C31—C30—C38 | −1.6 (5) | C167—C65—C63—C61 | −0.6 (5) |
C39—C31—C30—C38 | 175.0 (3) | C88—N109—C102—C105 | −174.6 (3) |
C36—C34—C32—C31 | 0.6 (5) | C95—N109—C102—C105 | 58.2 (4) |
C30—C31—C32—C34 | 0.9 (5) | C30—C38—C49—C51 | 125.5 (3) |
C39—C31—C32—C34 | −175.7 (3) | C36—C38—C49—C51 | −53.1 (4) |
O110—C1—C9—C7 | 176.2 (3) | C30—C38—C49—C55 | −111.7 (3) |
C2—C1—C9—C7 | −0.3 (4) | C36—C38—C49—C55 | 69.6 (4) |
O110—C1—C9—C20 | −5.7 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N109—H115···S114 | 0.83 (4) | 2.26 (4) | 3.080 (3) | 171 (4) |
Crystal data top
C36H51O3SSi·C6H16N | F(000) = 1520 |
Mr = 694.11 | Dx = 1.113 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 3815 reflections |
a = 11.6801 (9) Å | θ = 3.1–29.4° |
b = 17.9212 (10) Å | µ = 0.14 mm−1 |
c = 20.1555 (15) Å | T = 150 K |
β = 100.954 (6)° | Block, colourless |
V = 4142.1 (5) Å3 | 0.34 × 0.22 × 0.13 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 7216 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.039 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26°, θmin = 3.2° |
rotation method scans | h = −14→14 |
19022 measured reflections | k = −19→22 |
7810 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.01 | Δρmax = 0.23 e Å−3 |
7810 reflections | Δρmin = −0.17 e Å−3 |
452 parameters | Absolute structure: Flack x determined using 3205 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
Si1 | 0.55626 (4) | 0.26140 (3) | 0.06097 (3) | 0.01445 (13) | |
S114 | 0.40810 (5) | 0.20879 (3) | 0.01650 (3) | 0.02146 (13) | |
O112 | 0.54732 (13) | 0.35346 (8) | 0.05794 (8) | 0.0181 (3) | |
O110 | 0.59257 (13) | 0.23884 (8) | 0.14250 (8) | 0.0177 (3) | |
O111 | 0.67377 (14) | 0.24773 (8) | 0.02844 (8) | 0.0185 (3) | |
N109 | 0.19765 (18) | 0.28372 (11) | −0.07493 (10) | 0.0222 (4) | |
H115 | 0.266 (3) | 0.2664 (14) | −0.0511 (14) | 0.018 (6)* | |
C38 | 0.7317 (2) | 0.14370 (12) | −0.03375 (12) | 0.0212 (5) | |
C78 | 0.5842 (2) | 0.38475 (13) | −0.07806 (12) | 0.0226 (5) | |
H79 | 0.5391 | 0.3436 | −0.0638 | 0.027* | |
C1 | 0.53260 (19) | 0.19626 (12) | 0.18209 (11) | 0.0174 (4) | |
C5 | 0.4244 (2) | 0.11108 (14) | 0.26751 (13) | 0.0270 (5) | |
H6 | 0.3882 | 0.0826 | 0.2961 | 0.032* | |
C31 | 0.8571 (2) | 0.18966 (13) | 0.07026 (12) | 0.0212 (5) | |
C2 | 0.4383 (2) | 0.22653 (13) | 0.20655 (12) | 0.0199 (5) | |
C39 | 0.8817 (2) | 0.24697 (13) | 0.12729 (13) | 0.0234 (5) | |
H40 | 0.8073 | 0.2598 | 0.14 | 0.028* | |
C45 | 0.9318 (2) | 0.31828 (14) | 0.10204 (15) | 0.0307 (6) | |
H46 | 1.0061 | 0.3075 | 0.0904 | 0.046* | |
H47 | 0.9415 | 0.3554 | 0.137 | 0.046* | |
H48 | 0.8794 | 0.3366 | 0.0629 | 0.046* | |
C10 | 0.3948 (2) | 0.30564 (13) | 0.19132 (13) | 0.0226 (5) | |
H11 | 0.4329 | 0.3256 | 0.1557 | 0.027* | |
C41 | 0.9630 (2) | 0.21747 (16) | 0.19026 (14) | 0.0330 (6) | |
H42 | 0.9329 | 0.1713 | 0.2039 | 0.049* | |
H43 | 0.9679 | 0.2533 | 0.2261 | 0.049* | |
H44 | 1.0392 | 0.2093 | 0.1803 | 0.049* | |
C22 | 0.6260 (3) | 0.04990 (16) | 0.10513 (15) | 0.0369 (6) | |
H23 | 0.5847 | 0.006 | 0.1145 | 0.055* | |
H24 | 0.6895 | 0.0358 | 0.0838 | 0.055* | |
H25 | 0.5739 | 0.0822 | 0.0756 | 0.055* | |
C34 | 0.9214 (2) | 0.08725 (14) | 0.00793 (15) | 0.0318 (6) | |
H35 | 0.9771 | 0.0515 | 0.0033 | 0.038* | |
C20 | 0.6733 (2) | 0.09074 (13) | 0.17104 (13) | 0.0239 (5) | |
H21 | 0.7217 | 0.1322 | 0.1605 | 0.029* | |
C3 | 0.3847 (2) | 0.18211 (14) | 0.24927 (12) | 0.0237 (5) | |
H4 | 0.3212 | 0.2009 | 0.2656 | 0.028* | |
C84 | 0.4982 (3) | 0.43934 (16) | −0.11949 (16) | 0.0368 (6) | |
H85 | 0.5398 | 0.4823 | −0.1307 | 0.055* | |
H86 | 0.4414 | 0.4546 | −0.0935 | 0.055* | |
H87 | 0.4597 | 0.4154 | −0.1602 | 0.055* | |
C95 | 0.1072 (2) | 0.25011 (15) | −0.03936 (14) | 0.0279 (5) | |
H96 | 0.1252 | 0.2642 | 0.0079 | 0.034* | |
H97 | 0.112 | 0.1962 | −0.0417 | 0.034* | |
C30 | 0.75226 (19) | 0.19224 (12) | 0.02244 (12) | 0.0182 (4) | |
C61 | 0.7638 (2) | 0.50320 (14) | 0.09678 (15) | 0.0320 (6) | |
H62 | 0.8012 | 0.5307 | 0.1337 | 0.038* | |
C32 | 0.9401 (2) | 0.13654 (14) | 0.06229 (13) | 0.0271 (5) | |
H33 | 1.0094 | 0.1339 | 0.0938 | 0.033* | |
C68 | 0.6589 (2) | 0.43453 (14) | 0.17677 (13) | 0.0268 (5) | |
H69 | 0.6058 | 0.3919 | 0.1744 | 0.032* | |
C70 | 0.7683 (3) | 0.41673 (16) | 0.22852 (15) | 0.0370 (6) | |
H71 | 0.8046 | 0.3728 | 0.2147 | 0.055* | |
H72 | 0.7477 | 0.4082 | 0.2718 | 0.055* | |
H73 | 0.8216 | 0.4579 | 0.2317 | 0.055* | |
C105 | 0.2240 (3) | 0.39817 (16) | −0.00330 (16) | 0.0403 (7) | |
H106 | 0.2373 | 0.4509 | −0.005 | 0.06* | |
H107 | 0.2918 | 0.3744 | 0.0224 | 0.06* | |
H108 | 0.1582 | 0.389 | 0.0178 | 0.06* | |
C9 | 0.57391 (19) | 0.12372 (12) | 0.19993 (11) | 0.0193 (4) | |
C91 | 0.2937 (3) | 0.26519 (18) | −0.17497 (16) | 0.0392 (7) | |
H92 | 0.2847 | 0.2402 | −0.2178 | 0.059* | |
H93 | 0.3606 | 0.2456 | −0.1449 | 0.059* | |
H94 | 0.304 | 0.3177 | −0.1812 | 0.059* | |
C16 | 0.2631 (2) | 0.30863 (16) | 0.16579 (14) | 0.0321 (6) | |
H17 | 0.2416 | 0.273 | 0.13 | 0.048* | |
H18 | 0.2413 | 0.3578 | 0.1491 | 0.048* | |
H19 | 0.2237 | 0.297 | 0.2022 | 0.048* | |
C60 | 0.6852 (2) | 0.44734 (12) | 0.10668 (13) | 0.0228 (5) | |
C36 | 0.8193 (2) | 0.09208 (13) | −0.03888 (14) | 0.0278 (5) | |
H37 | 0.8081 | 0.0596 | −0.0755 | 0.033* | |
C88 | 0.1863 (2) | 0.25263 (15) | −0.14504 (14) | 0.0304 (6) | |
H89 | 0.1199 | 0.2758 | −0.174 | 0.037* | |
H90 | 0.1711 | 0.1995 | −0.1439 | 0.037* | |
C12 | 0.4296 (2) | 0.35478 (14) | 0.25411 (14) | 0.0287 (6) | |
H13 | 0.3936 | 0.3361 | 0.2898 | 0.043* | |
H14 | 0.4043 | 0.4051 | 0.2435 | 0.043* | |
H15 | 0.5129 | 0.3539 | 0.2684 | 0.043* | |
C65 | 0.7302 (2) | 0.47895 (14) | −0.02148 (14) | 0.0302 (6) | |
H66 | 0.7456 | 0.49 | −0.064 | 0.036* | |
C80 | 0.6654 (3) | 0.35222 (18) | −0.12160 (16) | 0.0401 (7) | |
H81 | 0.6205 | 0.3246 | −0.1584 | 0.06* | |
H82 | 0.7208 | 0.3196 | −0.0947 | 0.06* | |
H83 | 0.706 | 0.392 | −0.1391 | 0.06* | |
C98 | −0.0164 (2) | 0.27396 (18) | −0.06864 (16) | 0.0383 (7) | |
H99 | −0.0331 | 0.2637 | −0.1162 | 0.058* | |
H100 | −0.0246 | 0.3265 | −0.0614 | 0.058* | |
H101 | −0.0698 | 0.2468 | −0.0469 | 0.058* | |
C167 | 0.6498 (2) | 0.42274 (13) | −0.01519 (12) | 0.0220 (5) | |
C59 | 0.62953 (19) | 0.40688 (11) | 0.04986 (12) | 0.0185 (4) | |
C26 | 0.7517 (3) | 0.03854 (17) | 0.21967 (17) | 0.0413 (7) | |
H27 | 0.7099 | −0.0064 | 0.2253 | 0.062* | |
H28 | 0.7747 | 0.0627 | 0.2627 | 0.062* | |
H29 | 0.8199 | 0.0265 | 0.2016 | 0.062* | |
C7 | 0.5183 (2) | 0.08235 (13) | 0.24301 (13) | 0.0249 (5) | |
H8 | 0.5447 | 0.0345 | 0.2556 | 0.03* | |
C74 | 0.5974 (3) | 0.50292 (17) | 0.19895 (16) | 0.0410 (7) | |
H75 | 0.5806 | 0.4944 | 0.2431 | 0.061* | |
H76 | 0.5259 | 0.5115 | 0.1675 | 0.061* | |
H77 | 0.647 | 0.5458 | 0.2001 | 0.061* | |
C63 | 0.7873 (3) | 0.51856 (15) | 0.03397 (15) | 0.0347 (6) | |
H64 | 0.8411 | 0.5553 | 0.0287 | 0.042* | |
C102 | 0.1998 (2) | 0.36690 (14) | −0.07414 (14) | 0.0296 (6) | |
H103 | 0.1253 | 0.3856 | −0.0979 | 0.036* | |
H104 | 0.2595 | 0.3842 | −0.098 | 0.036* | |
C49 | 0.6219 (2) | 0.14621 (13) | −0.08790 (13) | 0.0242 (5) | |
H50 | 0.5763 | 0.1899 | −0.0794 | 0.029* | |
C55 | 0.5457 (2) | 0.07665 (15) | −0.08719 (15) | 0.0342 (6) | |
H56 | 0.5877 | 0.0334 | −0.0974 | 0.051* | |
H57 | 0.4755 | 0.0819 | −0.1205 | 0.051* | |
H58 | 0.5261 | 0.0711 | −0.0433 | 0.051* | |
C51 | 0.6516 (3) | 0.15457 (16) | −0.15873 (14) | 0.0368 (6) | |
H52 | 0.6997 | 0.1979 | −0.1597 | 0.055* | |
H53 | 0.5809 | 0.16 | −0.1916 | 0.055* | |
H54 | 0.6927 | 0.111 | −0.1691 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0134 (3) | 0.0145 (3) | 0.0158 (3) | −0.0002 (2) | 0.0036 (2) | 0.0000 (2) |
S114 | 0.0171 (3) | 0.0182 (2) | 0.0271 (3) | −0.0029 (2) | −0.0010 (2) | 0.0004 (2) |
O112 | 0.0169 (7) | 0.0164 (7) | 0.0213 (8) | −0.0010 (6) | 0.0046 (6) | 0.0000 (6) |
O110 | 0.0161 (7) | 0.0203 (7) | 0.0170 (8) | −0.0006 (6) | 0.0040 (6) | 0.0025 (6) |
O111 | 0.0179 (7) | 0.0179 (7) | 0.0209 (9) | 0.0020 (6) | 0.0068 (7) | 0.0000 (6) |
N109 | 0.0199 (10) | 0.0274 (10) | 0.0187 (11) | 0.0003 (8) | 0.0017 (9) | 0.0019 (8) |
C38 | 0.0238 (12) | 0.0203 (11) | 0.0212 (12) | 0.0003 (9) | 0.0080 (10) | 0.0013 (9) |
C78 | 0.0261 (12) | 0.0224 (11) | 0.0200 (12) | −0.0039 (9) | 0.0057 (10) | 0.0018 (9) |
C1 | 0.0170 (10) | 0.0213 (11) | 0.0132 (11) | −0.0037 (8) | 0.0008 (9) | 0.0001 (8) |
C5 | 0.0347 (13) | 0.0277 (12) | 0.0205 (13) | −0.0087 (10) | 0.0105 (11) | 0.0004 (9) |
C31 | 0.0204 (11) | 0.0231 (11) | 0.0210 (12) | −0.0007 (9) | 0.0060 (10) | 0.0016 (9) |
C2 | 0.0186 (10) | 0.0248 (11) | 0.0156 (12) | −0.0024 (8) | 0.0012 (9) | −0.0007 (8) |
C39 | 0.0183 (11) | 0.0287 (13) | 0.0237 (13) | −0.0015 (9) | 0.0052 (10) | −0.0045 (9) |
C45 | 0.0273 (12) | 0.0300 (13) | 0.0356 (15) | −0.0056 (10) | 0.0082 (12) | −0.0065 (11) |
C10 | 0.0196 (11) | 0.0272 (12) | 0.0229 (13) | 0.0043 (9) | 0.0089 (10) | 0.0032 (9) |
C41 | 0.0270 (13) | 0.0454 (15) | 0.0250 (14) | −0.0053 (11) | 0.0010 (12) | −0.0037 (11) |
C22 | 0.0427 (16) | 0.0388 (15) | 0.0308 (15) | 0.0088 (12) | 0.0108 (13) | −0.0074 (12) |
C34 | 0.0304 (13) | 0.0278 (12) | 0.0374 (16) | 0.0109 (11) | 0.0067 (12) | −0.0030 (11) |
C20 | 0.0233 (11) | 0.0183 (11) | 0.0308 (14) | 0.0019 (9) | 0.0067 (11) | 0.0026 (9) |
C3 | 0.0233 (11) | 0.0304 (12) | 0.0193 (13) | −0.0036 (9) | 0.0088 (10) | −0.0033 (9) |
C84 | 0.0342 (14) | 0.0366 (14) | 0.0362 (16) | 0.0014 (12) | −0.0022 (13) | −0.0006 (12) |
C95 | 0.0249 (12) | 0.0367 (14) | 0.0221 (13) | −0.0041 (10) | 0.0042 (11) | 0.0072 (10) |
C30 | 0.0176 (10) | 0.0174 (10) | 0.0212 (12) | 0.0015 (8) | 0.0079 (10) | 0.0022 (8) |
C61 | 0.0353 (14) | 0.0260 (12) | 0.0332 (16) | −0.0119 (11) | 0.0030 (12) | −0.0048 (10) |
C32 | 0.0205 (12) | 0.0312 (12) | 0.0279 (15) | 0.0054 (10) | 0.0002 (11) | 0.0029 (10) |
C68 | 0.0327 (13) | 0.0252 (12) | 0.0225 (13) | −0.0078 (10) | 0.0054 (11) | −0.0037 (9) |
C70 | 0.0462 (16) | 0.0349 (14) | 0.0290 (16) | 0.0006 (12) | 0.0049 (13) | 0.0035 (11) |
C105 | 0.0588 (19) | 0.0290 (14) | 0.0332 (16) | 0.0056 (13) | 0.0092 (15) | −0.0036 (11) |
C9 | 0.0205 (11) | 0.0207 (11) | 0.0156 (12) | −0.0028 (9) | 0.0009 (9) | −0.0016 (9) |
C91 | 0.0455 (17) | 0.0459 (17) | 0.0300 (16) | −0.0051 (13) | 0.0171 (14) | −0.0095 (12) |
C16 | 0.0226 (12) | 0.0449 (15) | 0.0283 (15) | 0.0070 (11) | 0.0034 (11) | 0.0032 (11) |
C60 | 0.0248 (11) | 0.0182 (11) | 0.0249 (13) | −0.0025 (9) | 0.0034 (10) | −0.0001 (9) |
C36 | 0.0309 (13) | 0.0224 (11) | 0.0303 (14) | 0.0053 (10) | 0.0067 (11) | −0.0069 (10) |
C88 | 0.0314 (13) | 0.0379 (14) | 0.0214 (14) | −0.0039 (11) | 0.0034 (12) | −0.0056 (10) |
C12 | 0.0305 (13) | 0.0244 (12) | 0.0309 (15) | 0.0053 (10) | 0.0050 (12) | −0.0001 (10) |
C65 | 0.0354 (14) | 0.0292 (13) | 0.0268 (14) | −0.0082 (11) | 0.0083 (12) | 0.0055 (10) |
C80 | 0.0382 (16) | 0.0470 (17) | 0.0366 (17) | 0.0005 (13) | 0.0105 (14) | −0.0118 (13) |
C98 | 0.0236 (13) | 0.0629 (19) | 0.0285 (16) | −0.0019 (13) | 0.0048 (12) | 0.0086 (13) |
C167 | 0.0237 (11) | 0.0198 (11) | 0.0230 (13) | −0.0001 (9) | 0.0055 (10) | 0.0009 (9) |
C59 | 0.0164 (10) | 0.0138 (10) | 0.0254 (13) | −0.0016 (8) | 0.0039 (10) | 0.0022 (9) |
C26 | 0.0352 (15) | 0.0415 (16) | 0.0447 (19) | 0.0152 (12) | 0.0012 (14) | 0.0053 (13) |
C7 | 0.0332 (13) | 0.0199 (11) | 0.0210 (13) | −0.0032 (9) | 0.0036 (11) | 0.0026 (9) |
C74 | 0.0494 (17) | 0.0434 (16) | 0.0321 (17) | 0.0100 (13) | 0.0125 (15) | −0.0004 (13) |
C63 | 0.0375 (14) | 0.0283 (13) | 0.0388 (16) | −0.0152 (11) | 0.0088 (13) | 0.0016 (11) |
C102 | 0.0363 (14) | 0.0260 (12) | 0.0273 (14) | 0.0022 (10) | 0.0083 (12) | 0.0023 (10) |
C49 | 0.0259 (12) | 0.0260 (12) | 0.0200 (13) | 0.0048 (9) | 0.0028 (10) | −0.0035 (9) |
C55 | 0.0349 (14) | 0.0355 (14) | 0.0298 (15) | −0.0033 (11) | −0.0004 (12) | −0.0047 (11) |
C51 | 0.0474 (16) | 0.0417 (15) | 0.0222 (14) | 0.0102 (13) | 0.0088 (13) | −0.0004 (11) |
Geometric parameters (Å, º) top
Si1—O111 | 1.6481 (16) | C61—C60 | 1.398 (3) |
Si1—O112 | 1.6535 (15) | C61—H62 | 0.93 |
Si1—O110 | 1.6670 (16) | C32—H33 | 0.93 |
Si1—S114 | 2.0242 (8) | C68—C60 | 1.519 (3) |
O112—C59 | 1.387 (3) | C68—C70 | 1.522 (4) |
O110—C1 | 1.386 (3) | C68—C74 | 1.530 (4) |
O111—C30 | 1.373 (3) | C68—H69 | 0.98 |
N109—C102 | 1.491 (3) | C70—H71 | 0.96 |
N109—C88 | 1.501 (3) | C70—H72 | 0.96 |
N109—C95 | 1.510 (3) | C70—H73 | 0.96 |
N109—H115 | 0.91 (3) | C105—C102 | 1.510 (4) |
C38—C36 | 1.398 (3) | C105—H106 | 0.96 |
C38—C30 | 1.412 (3) | C105—H107 | 0.96 |
C38—C49 | 1.518 (4) | C105—H108 | 0.96 |
C78—C167 | 1.512 (3) | C9—C7 | 1.393 (3) |
C78—C80 | 1.525 (4) | C91—C88 | 1.509 (4) |
C78—C84 | 1.531 (4) | C91—H92 | 0.96 |
C78—H79 | 0.98 | C91—H93 | 0.96 |
C1—C2 | 1.399 (3) | C91—H94 | 0.96 |
C1—C9 | 1.409 (3) | C16—H17 | 0.96 |
C5—C3 | 1.381 (4) | C16—H18 | 0.96 |
C5—C7 | 1.385 (4) | C16—H19 | 0.96 |
C5—H6 | 0.93 | C60—C59 | 1.406 (3) |
C31—C32 | 1.390 (3) | C36—H37 | 0.93 |
C31—C30 | 1.408 (3) | C88—H89 | 0.97 |
C31—C39 | 1.527 (3) | C88—H90 | 0.97 |
C2—C3 | 1.404 (3) | C12—H13 | 0.96 |
C2—C10 | 1.518 (3) | C12—H14 | 0.96 |
C39—C41 | 1.527 (4) | C12—H15 | 0.96 |
C39—C45 | 1.532 (3) | C65—C63 | 1.384 (4) |
C39—H40 | 0.98 | C65—C167 | 1.399 (3) |
C45—H46 | 0.96 | C65—H66 | 0.93 |
C45—H47 | 0.96 | C80—H81 | 0.96 |
C45—H48 | 0.96 | C80—H82 | 0.96 |
C10—C16 | 1.527 (3) | C80—H83 | 0.96 |
C10—C12 | 1.532 (4) | C98—H99 | 0.96 |
C10—H11 | 0.98 | C98—H100 | 0.96 |
C41—H42 | 0.96 | C98—H101 | 0.96 |
C41—H43 | 0.96 | C167—C59 | 1.405 (3) |
C41—H44 | 0.96 | C26—H27 | 0.96 |
C22—C20 | 1.526 (4) | C26—H28 | 0.96 |
C22—H23 | 0.96 | C26—H29 | 0.96 |
C22—H24 | 0.96 | C7—H8 | 0.93 |
C22—H25 | 0.96 | C74—H75 | 0.96 |
C34—C36 | 1.375 (4) | C74—H76 | 0.96 |
C34—C32 | 1.392 (4) | C74—H77 | 0.96 |
C34—H35 | 0.93 | C63—H64 | 0.93 |
C20—C9 | 1.515 (3) | C102—H103 | 0.97 |
C20—C26 | 1.527 (4) | C102—H104 | 0.97 |
C20—H21 | 0.98 | C49—C55 | 1.534 (4) |
C3—H4 | 0.93 | C49—C51 | 1.539 (4) |
C84—H85 | 0.96 | C49—H50 | 0.98 |
C84—H86 | 0.96 | C55—H56 | 0.96 |
C84—H87 | 0.96 | C55—H57 | 0.96 |
C95—C98 | 1.514 (4) | C55—H58 | 0.96 |
C95—H96 | 0.97 | C51—H52 | 0.96 |
C95—H97 | 0.97 | C51—H53 | 0.96 |
C61—C63 | 1.373 (4) | C51—H54 | 0.96 |
| | | |
O111—Si1—O112 | 100.67 (8) | H71—C70—H72 | 109.5 |
O111—Si1—O110 | 106.32 (8) | C68—C70—H73 | 109.5 |
O112—Si1—O110 | 106.32 (8) | H71—C70—H73 | 109.5 |
O111—Si1—S114 | 117.46 (6) | H72—C70—H73 | 109.5 |
O112—Si1—S114 | 113.94 (7) | C102—C105—H106 | 109.5 |
O110—Si1—S114 | 111.07 (6) | C102—C105—H107 | 109.5 |
C59—O112—Si1 | 130.74 (14) | H106—C105—H107 | 109.5 |
C1—O110—Si1 | 129.73 (14) | C102—C105—H108 | 109.5 |
C30—O111—Si1 | 139.73 (14) | H106—C105—H108 | 109.5 |
C102—N109—C88 | 112.29 (19) | H107—C105—H108 | 109.5 |
C102—N109—C95 | 113.95 (19) | C7—C9—C1 | 118.2 (2) |
C88—N109—C95 | 110.73 (19) | C7—C9—C20 | 121.0 (2) |
C102—N109—H115 | 108.9 (16) | C1—C9—C20 | 120.81 (19) |
C88—N109—H115 | 106.5 (17) | C88—C91—H92 | 109.5 |
C95—N109—H115 | 103.8 (17) | C88—C91—H93 | 109.5 |
C36—C38—C30 | 116.9 (2) | H92—C91—H93 | 109.5 |
C36—C38—C49 | 119.8 (2) | C88—C91—H94 | 109.5 |
C30—C38—C49 | 123.4 (2) | H92—C91—H94 | 109.5 |
C167—C78—C80 | 112.5 (2) | H93—C91—H94 | 109.5 |
C167—C78—C84 | 110.2 (2) | C10—C16—H17 | 109.5 |
C80—C78—C84 | 110.2 (2) | C10—C16—H18 | 109.5 |
C167—C78—H79 | 107.9 | H17—C16—H18 | 109.5 |
C80—C78—H79 | 107.9 | C10—C16—H19 | 109.5 |
C84—C78—H79 | 107.9 | H17—C16—H19 | 109.5 |
O110—C1—C2 | 120.47 (19) | H18—C16—H19 | 109.5 |
O110—C1—C9 | 117.95 (18) | C61—C60—C59 | 117.9 (2) |
C2—C1—C9 | 121.47 (19) | C61—C60—C68 | 119.7 (2) |
C3—C5—C7 | 119.8 (2) | C59—C60—C68 | 122.4 (2) |
C3—C5—H6 | 120.1 | C34—C36—C38 | 122.8 (2) |
C7—C5—H6 | 120.1 | C34—C36—H37 | 118.6 |
C32—C31—C30 | 118.6 (2) | C38—C36—H37 | 118.6 |
C32—C31—C39 | 120.8 (2) | N109—C88—C91 | 112.9 (2) |
C30—C31—C39 | 120.5 (2) | N109—C88—H89 | 109 |
C1—C2—C3 | 118.0 (2) | C91—C88—H89 | 109 |
C1—C2—C10 | 123.15 (19) | N109—C88—H90 | 109 |
C3—C2—C10 | 118.8 (2) | C91—C88—H90 | 109 |
C31—C39—C41 | 113.0 (2) | H89—C88—H90 | 107.8 |
C31—C39—C45 | 109.9 (2) | C10—C12—H13 | 109.5 |
C41—C39—C45 | 110.4 (2) | C10—C12—H14 | 109.5 |
C31—C39—H40 | 107.8 | H13—C12—H14 | 109.5 |
C41—C39—H40 | 107.8 | C10—C12—H15 | 109.5 |
C45—C39—H40 | 107.8 | H13—C12—H15 | 109.5 |
C39—C45—H46 | 109.5 | H14—C12—H15 | 109.5 |
C39—C45—H47 | 109.5 | C63—C65—C167 | 121.7 (2) |
H46—C45—H47 | 109.5 | C63—C65—H66 | 119.2 |
C39—C45—H48 | 109.5 | C167—C65—H66 | 119.2 |
H46—C45—H48 | 109.5 | C78—C80—H81 | 109.5 |
H47—C45—H48 | 109.5 | C78—C80—H82 | 109.5 |
C2—C10—C16 | 112.2 (2) | H81—C80—H82 | 109.5 |
C2—C10—C12 | 110.1 (2) | C78—C80—H83 | 109.5 |
C16—C10—C12 | 110.5 (2) | H81—C80—H83 | 109.5 |
C2—C10—H11 | 108 | H82—C80—H83 | 109.5 |
C16—C10—H11 | 108 | C95—C98—H99 | 109.5 |
C12—C10—H11 | 108 | C95—C98—H100 | 109.5 |
C39—C41—H42 | 109.5 | H99—C98—H100 | 109.5 |
C39—C41—H43 | 109.5 | C95—C98—H101 | 109.5 |
H42—C41—H43 | 109.5 | H99—C98—H101 | 109.5 |
C39—C41—H44 | 109.5 | H100—C98—H101 | 109.5 |
H42—C41—H44 | 109.5 | C65—C167—C59 | 117.7 (2) |
H43—C41—H44 | 109.5 | C65—C167—C78 | 119.4 (2) |
C20—C22—H23 | 109.5 | C59—C167—C78 | 122.9 (2) |
C20—C22—H24 | 109.5 | O112—C59—C167 | 119.5 (2) |
H23—C22—H24 | 109.5 | O112—C59—C60 | 118.9 (2) |
C20—C22—H25 | 109.5 | C167—C59—C60 | 121.5 (2) |
H23—C22—H25 | 109.5 | C20—C26—H27 | 109.5 |
H24—C22—H25 | 109.5 | C20—C26—H28 | 109.5 |
C36—C34—C32 | 119.1 (2) | H27—C26—H28 | 109.5 |
C36—C34—H35 | 120.5 | C20—C26—H29 | 109.5 |
C32—C34—H35 | 120.5 | H27—C26—H29 | 109.5 |
C9—C20—C22 | 110.1 (2) | H28—C26—H29 | 109.5 |
C9—C20—C26 | 113.7 (2) | C5—C7—C9 | 121.3 (2) |
C22—C20—C26 | 109.8 (2) | C5—C7—H8 | 119.4 |
C9—C20—H21 | 107.6 | C9—C7—H8 | 119.4 |
C22—C20—H21 | 107.6 | C68—C74—H75 | 109.5 |
C26—C20—H21 | 107.6 | C68—C74—H76 | 109.5 |
C5—C3—C2 | 121.3 (2) | H75—C74—H76 | 109.5 |
C5—C3—H4 | 119.3 | C68—C74—H77 | 109.5 |
C2—C3—H4 | 119.3 | H75—C74—H77 | 109.5 |
C78—C84—H85 | 109.5 | H76—C74—H77 | 109.5 |
C78—C84—H86 | 109.5 | C61—C63—C65 | 119.5 (2) |
H85—C84—H86 | 109.5 | C61—C63—H64 | 120.3 |
C78—C84—H87 | 109.5 | C65—C63—H64 | 120.3 |
H85—C84—H87 | 109.5 | N109—C102—C105 | 112.4 (2) |
H86—C84—H87 | 109.5 | N109—C102—H103 | 109.1 |
N109—C95—C98 | 113.8 (2) | C105—C102—H103 | 109.1 |
N109—C95—H96 | 108.8 | N109—C102—H104 | 109.1 |
C98—C95—H96 | 108.8 | C105—C102—H104 | 109.1 |
N109—C95—H97 | 108.8 | H103—C102—H104 | 107.9 |
C98—C95—H97 | 108.8 | C38—C49—C55 | 112.4 (2) |
H96—C95—H97 | 107.7 | C38—C49—C51 | 111.2 (2) |
O111—C30—C31 | 118.1 (2) | C55—C49—C51 | 108.7 (2) |
O111—C30—C38 | 120.1 (2) | C38—C49—H50 | 108.1 |
C31—C30—C38 | 121.5 (2) | C55—C49—H50 | 108.1 |
C63—C61—C60 | 121.8 (3) | C51—C49—H50 | 108.1 |
C63—C61—H62 | 119.1 | C49—C55—H56 | 109.5 |
C60—C61—H62 | 119.1 | C49—C55—H57 | 109.5 |
C31—C32—C34 | 121.1 (2) | H56—C55—H57 | 109.5 |
C31—C32—H33 | 119.4 | C49—C55—H58 | 109.5 |
C34—C32—H33 | 119.4 | H56—C55—H58 | 109.5 |
C60—C68—C70 | 112.2 (2) | H57—C55—H58 | 109.5 |
C60—C68—C74 | 109.9 (2) | C49—C51—H52 | 109.5 |
C70—C68—C74 | 110.3 (2) | C49—C51—H53 | 109.5 |
C60—C68—H69 | 108.1 | H52—C51—H53 | 109.5 |
C70—C68—H69 | 108.1 | C49—C51—H54 | 109.5 |
C74—C68—H69 | 108.1 | H52—C51—H54 | 109.5 |
C68—C70—H71 | 109.5 | H53—C51—H54 | 109.5 |
C68—C70—H72 | 109.5 | | |
| | | |
O111—Si1—O112—C59 | −16.9 (2) | C2—C1—C9—C20 | 177.8 (2) |
O110—Si1—O112—C59 | 93.8 (2) | C22—C20—C9—C7 | 88.2 (3) |
S114—Si1—O112—C59 | −143.58 (18) | C26—C20—C9—C7 | −35.5 (3) |
O111—Si1—O110—C1 | −134.53 (17) | C22—C20—C9—C1 | −89.6 (3) |
O112—Si1—O110—C1 | 118.80 (17) | C26—C20—C9—C1 | 146.7 (2) |
S114—Si1—O110—C1 | −5.65 (18) | C63—C61—C60—C59 | −0.3 (4) |
O112—Si1—O111—C30 | 166.1 (2) | C63—C61—C60—C68 | −177.7 (3) |
O110—Si1—O111—C30 | 55.4 (2) | C70—C68—C60—C61 | −57.9 (3) |
S114—Si1—O111—C30 | −69.7 (2) | C74—C68—C60—C61 | 65.2 (3) |
Si1—O110—C1—C2 | −77.8 (2) | C70—C68—C60—C59 | 124.8 (2) |
Si1—O110—C1—C9 | 105.9 (2) | C74—C68—C60—C59 | −112.1 (3) |
O110—C1—C2—C3 | −176.8 (2) | C32—C34—C36—C38 | −1.2 (4) |
C9—C1—C2—C3 | −0.6 (3) | C30—C38—C36—C34 | 0.3 (4) |
O110—C1—C2—C10 | 0.8 (3) | C49—C38—C36—C34 | 179.3 (2) |
C9—C1—C2—C10 | 177.0 (2) | C102—N109—C88—C91 | 68.9 (3) |
C32—C31—C39—C41 | −31.0 (3) | C95—N109—C88—C91 | −162.5 (2) |
C30—C31—C39—C41 | 152.6 (2) | C63—C65—C167—C59 | −0.8 (4) |
C32—C31—C39—C45 | 92.8 (3) | C63—C65—C167—C78 | 176.0 (2) |
C30—C31—C39—C45 | −83.6 (3) | C80—C78—C167—C65 | 54.6 (3) |
C1—C2—C10—C16 | 130.0 (2) | C84—C78—C167—C65 | −68.7 (3) |
C3—C2—C10—C16 | −52.5 (3) | C80—C78—C167—C59 | −128.7 (2) |
C1—C2—C10—C12 | −106.5 (2) | C84—C78—C167—C59 | 107.9 (3) |
C3—C2—C10—C12 | 71.0 (3) | Si1—O112—C59—C167 | 80.8 (3) |
C7—C5—C3—C2 | −0.5 (4) | Si1—O112—C59—C60 | −103.3 (2) |
C1—C2—C3—C5 | 0.9 (4) | C65—C167—C59—O112 | 177.6 (2) |
C10—C2—C3—C5 | −176.8 (2) | C78—C167—C59—O112 | 1.0 (3) |
C102—N109—C95—C98 | 59.1 (3) | C65—C167—C59—C60 | 1.8 (3) |
C88—N109—C95—C98 | −68.6 (3) | C78—C167—C59—C60 | −174.8 (2) |
Si1—O111—C30—C31 | −95.5 (3) | C61—C60—C59—O112 | −177.2 (2) |
Si1—O111—C30—C38 | 90.0 (3) | C68—C60—C59—O112 | 0.2 (3) |
C32—C31—C30—O111 | −176.2 (2) | C61—C60—C59—C167 | −1.4 (3) |
C39—C31—C30—O111 | 0.4 (3) | C68—C60—C59—C167 | 176.0 (2) |
C32—C31—C30—C38 | −1.7 (3) | C3—C5—C7—C9 | −0.1 (4) |
C39—C31—C30—C38 | 174.8 (2) | C1—C9—C7—C5 | 0.4 (3) |
C36—C38—C30—O111 | 175.6 (2) | C20—C9—C7—C5 | −177.4 (2) |
C49—C38—C30—O111 | −3.4 (3) | C60—C61—C63—C65 | 1.3 (4) |
C36—C38—C30—C31 | 1.2 (3) | C167—C65—C63—C61 | −0.8 (4) |
C49—C38—C30—C31 | −177.8 (2) | C88—N109—C102—C105 | −174.0 (2) |
C30—C31—C32—C34 | 0.7 (4) | C95—N109—C102—C105 | 59.1 (3) |
C39—C31—C32—C34 | −175.8 (2) | C36—C38—C49—C55 | 68.6 (3) |
C36—C34—C32—C31 | 0.7 (4) | C30—C38—C49—C55 | −112.4 (3) |
O110—C1—C9—C7 | 176.2 (2) | C36—C38—C49—C51 | −53.6 (3) |
C2—C1—C9—C7 | −0.1 (3) | C30—C38—C49—C51 | 125.4 (2) |
O110—C1—C9—C20 | −5.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N109—H115···S114 | 0.91 (3) | 2.19 (3) | 3.085 (2) | 168 (2) |
Crystal data top
C36H51O3SSi·C6H16N | F(000) = 1520 |
Mr = 694.11 | Dx = 1.109 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 3002 reflections |
a = 11.6874 (11) Å | θ = 3.1–29.2° |
b = 17.9345 (12) Å | µ = 0.14 mm−1 |
c = 20.1975 (18) Å | T = 165 K |
β = 100.976 (7)° | Block, colourless |
V = 4156.1 (6) Å3 | 0.34 × 0.22 × 0.13 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 7217 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.051 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.2° |
rotation method scans | h = −14→14 |
21609 measured reflections | k = −19→22 |
8083 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 0.98 | Δρmax = 0.34 e Å−3 |
8083 reflections | Δρmin = −0.20 e Å−3 |
452 parameters | Absolute structure: Flack x determined using 3164 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
Si1 | 0.55628 (5) | 0.26160 (3) | 0.06094 (3) | 0.01606 (15) | |
S114 | 0.40836 (5) | 0.20896 (3) | 0.01656 (4) | 0.02412 (15) | |
O112 | 0.54733 (15) | 0.35365 (9) | 0.05795 (10) | 0.0206 (4) | |
O110 | 0.59247 (15) | 0.23911 (10) | 0.14231 (9) | 0.0199 (4) | |
O111 | 0.67364 (16) | 0.24789 (9) | 0.02840 (9) | 0.0205 (4) | |
N109 | 0.1976 (2) | 0.28351 (13) | −0.07467 (12) | 0.0252 (5) | |
H115 | 0.265 (3) | 0.2655 (17) | −0.0509 (17) | 0.023 (8)* | |
C38 | 0.7318 (2) | 0.14388 (15) | −0.03335 (14) | 0.0235 (6) | |
C78 | 0.5840 (2) | 0.38520 (15) | −0.07808 (14) | 0.0255 (6) | |
H79 | 0.5391 | 0.344 | −0.0639 | 0.031* | |
C1 | 0.5326 (2) | 0.19640 (14) | 0.18200 (13) | 0.0196 (5) | |
C5 | 0.4246 (3) | 0.11129 (16) | 0.26724 (15) | 0.0300 (6) | |
H6 | 0.3883 | 0.0829 | 0.2958 | 0.036* | |
C31 | 0.8570 (2) | 0.18988 (15) | 0.07029 (14) | 0.0239 (6) | |
C2 | 0.4386 (2) | 0.22656 (15) | 0.20650 (14) | 0.0221 (5) | |
C39 | 0.8813 (2) | 0.24747 (15) | 0.12710 (15) | 0.0258 (6) | |
H40 | 0.8069 | 0.2603 | 0.1397 | 0.031* | |
C45 | 0.9313 (3) | 0.31847 (18) | 0.10175 (18) | 0.0357 (7) | |
H46 | 1.0053 | 0.3076 | 0.0899 | 0.054* | |
H47 | 0.9413 | 0.3556 | 0.1366 | 0.054* | |
H48 | 0.8786 | 0.3368 | 0.0628 | 0.054* | |
C10 | 0.3950 (2) | 0.30569 (15) | 0.19143 (15) | 0.0251 (6) | |
H11 | 0.4331 | 0.3257 | 0.156 | 0.03* | |
C41 | 0.9626 (3) | 0.2183 (2) | 0.19006 (17) | 0.0373 (7) | |
H42 | 0.9315 | 0.1729 | 0.2046 | 0.056* | |
H43 | 0.9693 | 0.2548 | 0.2253 | 0.056* | |
H44 | 1.0382 | 0.2088 | 0.1798 | 0.056* | |
C22 | 0.6252 (3) | 0.04929 (19) | 0.10534 (18) | 0.0422 (8) | |
H23 | 0.5868 | 0.0045 | 0.1154 | 0.063* | |
H24 | 0.6882 | 0.0367 | 0.0831 | 0.063* | |
H25 | 0.5705 | 0.0805 | 0.0764 | 0.063* | |
C34 | 0.9210 (3) | 0.08760 (16) | 0.00818 (17) | 0.0351 (7) | |
H35 | 0.9768 | 0.0519 | 0.0036 | 0.042* | |
C20 | 0.6728 (2) | 0.09073 (15) | 0.17070 (16) | 0.0274 (6) | |
H21 | 0.7206 | 0.1321 | 0.1596 | 0.033* | |
C3 | 0.3855 (2) | 0.18207 (16) | 0.24921 (14) | 0.0268 (6) | |
H4 | 0.3223 | 0.2009 | 0.2657 | 0.032* | |
C84 | 0.4980 (3) | 0.43940 (19) | −0.1193 (2) | 0.0416 (8) | |
H85 | 0.5391 | 0.4826 | −0.1303 | 0.062* | |
H86 | 0.441 | 0.4543 | −0.0933 | 0.062* | |
H87 | 0.4597 | 0.4155 | −0.16 | 0.062* | |
C95 | 0.1072 (3) | 0.24983 (17) | −0.03928 (16) | 0.0318 (7) | |
H96 | 0.1249 | 0.264 | 0.0079 | 0.038* | |
H97 | 0.1123 | 0.1959 | −0.0415 | 0.038* | |
C30 | 0.7522 (2) | 0.19229 (14) | 0.02247 (13) | 0.0202 (5) | |
C61 | 0.7631 (3) | 0.50339 (17) | 0.09670 (17) | 0.0352 (7) | |
H62 | 0.8007 | 0.5308 | 0.1336 | 0.042* | |
C32 | 0.9399 (2) | 0.13699 (17) | 0.06233 (16) | 0.0309 (6) | |
H33 | 1.0092 | 0.1345 | 0.0937 | 0.037* | |
C68 | 0.6586 (3) | 0.43474 (16) | 0.17673 (15) | 0.0299 (6) | |
H69 | 0.6056 | 0.392 | 0.1743 | 0.036* | |
C70 | 0.7678 (3) | 0.4170 (2) | 0.22835 (17) | 0.0419 (8) | |
H71 | 0.8044 | 0.3733 | 0.2144 | 0.063* | |
H72 | 0.7471 | 0.408 | 0.2714 | 0.063* | |
H73 | 0.8207 | 0.4583 | 0.2318 | 0.063* | |
C105 | 0.2245 (4) | 0.39794 (19) | −0.00353 (18) | 0.0462 (9) | |
H106 | 0.2373 | 0.4507 | −0.0054 | 0.069* | |
H107 | 0.2927 | 0.3745 | 0.0219 | 0.069* | |
H108 | 0.1592 | 0.3886 | 0.0178 | 0.069* | |
C9 | 0.5738 (2) | 0.12395 (14) | 0.19974 (13) | 0.0222 (5) | |
C91 | 0.2938 (3) | 0.2645 (2) | −0.17461 (19) | 0.0440 (8) | |
H92 | 0.284 | 0.2405 | −0.2178 | 0.066* | |
H93 | 0.3603 | 0.2438 | −0.1451 | 0.066* | |
H94 | 0.3056 | 0.317 | −0.1799 | 0.066* | |
C16 | 0.2631 (3) | 0.30832 (19) | 0.16559 (17) | 0.0368 (7) | |
H17 | 0.2421 | 0.2728 | 0.1298 | 0.055* | |
H18 | 0.2411 | 0.3574 | 0.149 | 0.055* | |
H19 | 0.2236 | 0.2964 | 0.2018 | 0.055* | |
C60 | 0.6848 (3) | 0.44762 (14) | 0.10648 (15) | 0.0257 (6) | |
C36 | 0.8190 (3) | 0.09215 (16) | −0.03848 (16) | 0.0312 (6) | |
H37 | 0.8076 | 0.0595 | −0.0749 | 0.037* | |
C88 | 0.1868 (3) | 0.25254 (18) | −0.14500 (16) | 0.0348 (7) | |
H89 | 0.171 | 0.1995 | −0.144 | 0.042* | |
H90 | 0.1208 | 0.2759 | −0.174 | 0.042* | |
C12 | 0.4294 (3) | 0.35498 (16) | 0.25414 (16) | 0.0320 (7) | |
H13 | 0.3924 | 0.3368 | 0.2895 | 0.048* | |
H14 | 0.4049 | 0.4053 | 0.2433 | 0.048* | |
H15 | 0.5125 | 0.3537 | 0.2689 | 0.048* | |
C65 | 0.7296 (3) | 0.47926 (17) | −0.02151 (16) | 0.0343 (7) | |
H66 | 0.7451 | 0.4902 | −0.0639 | 0.041* | |
C80 | 0.6650 (3) | 0.3527 (2) | −0.12175 (19) | 0.0446 (8) | |
H81 | 0.6198 | 0.3263 | −0.1591 | 0.067* | |
H82 | 0.7191 | 0.319 | −0.0953 | 0.067* | |
H83 | 0.7071 | 0.3924 | −0.1383 | 0.067* | |
C98 | −0.0164 (3) | 0.2734 (2) | −0.06883 (18) | 0.0422 (8) | |
H99 | −0.0321 | 0.2643 | −0.1165 | 0.063* | |
H100 | −0.0255 | 0.3256 | −0.0606 | 0.063* | |
H101 | −0.0699 | 0.2453 | −0.0481 | 0.063* | |
C167 | 0.6496 (2) | 0.42314 (15) | −0.01512 (14) | 0.0246 (6) | |
C59 | 0.6297 (2) | 0.40713 (14) | 0.04985 (14) | 0.0214 (5) | |
C26 | 0.7519 (3) | 0.0395 (2) | 0.2193 (2) | 0.0464 (9) | |
H27 | 0.711 | −0.0058 | 0.2251 | 0.07* | |
H28 | 0.7743 | 0.0639 | 0.2621 | 0.07* | |
H29 | 0.8203 | 0.028 | 0.2014 | 0.07* | |
C7 | 0.5184 (3) | 0.08234 (16) | 0.24268 (14) | 0.0274 (6) | |
H8 | 0.5448 | 0.0345 | 0.2551 | 0.033* | |
C74 | 0.5968 (3) | 0.5028 (2) | 0.19881 (18) | 0.0456 (8) | |
H75 | 0.5814 | 0.4945 | 0.2432 | 0.068* | |
H76 | 0.5246 | 0.5107 | 0.1679 | 0.068* | |
H77 | 0.6455 | 0.5459 | 0.1992 | 0.068* | |
C63 | 0.7863 (3) | 0.51895 (18) | 0.03372 (17) | 0.0395 (8) | |
H64 | 0.8398 | 0.5559 | 0.0285 | 0.047* | |
C102 | 0.1998 (3) | 0.36665 (17) | −0.07408 (16) | 0.0340 (7) | |
H103 | 0.1251 | 0.3853 | −0.0976 | 0.041* | |
H104 | 0.2591 | 0.3839 | −0.0981 | 0.041* | |
C49 | 0.6219 (3) | 0.14621 (16) | −0.08751 (15) | 0.0272 (6) | |
H50 | 0.5762 | 0.1898 | −0.0791 | 0.033* | |
C55 | 0.5460 (3) | 0.07686 (18) | −0.08677 (18) | 0.0378 (7) | |
H56 | 0.5882 | 0.0336 | −0.0966 | 0.057* | |
H57 | 0.4761 | 0.082 | −0.1202 | 0.057* | |
H58 | 0.5261 | 0.0715 | −0.0431 | 0.057* | |
C51 | 0.6522 (3) | 0.1547 (2) | −0.15820 (17) | 0.0410 (8) | |
H52 | 0.7005 | 0.1979 | −0.1589 | 0.062* | |
H53 | 0.5818 | 0.1603 | −0.1911 | 0.062* | |
H54 | 0.6933 | 0.1112 | −0.1685 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0148 (3) | 0.0161 (3) | 0.0177 (4) | −0.0002 (3) | 0.0041 (3) | 0.0002 (3) |
S114 | 0.0194 (3) | 0.0204 (3) | 0.0302 (4) | −0.0033 (3) | −0.0009 (3) | 0.0005 (3) |
O112 | 0.0193 (8) | 0.0184 (8) | 0.0247 (10) | −0.0012 (7) | 0.0058 (7) | −0.0003 (8) |
O110 | 0.0181 (8) | 0.0226 (9) | 0.0195 (10) | −0.0008 (7) | 0.0051 (7) | 0.0027 (7) |
O111 | 0.0204 (9) | 0.0208 (9) | 0.0221 (10) | 0.0017 (7) | 0.0082 (8) | −0.0004 (7) |
N109 | 0.0226 (12) | 0.0296 (12) | 0.0222 (13) | 0.0004 (10) | 0.0014 (10) | 0.0025 (9) |
C38 | 0.0246 (13) | 0.0244 (13) | 0.0224 (14) | 0.0005 (10) | 0.0067 (12) | 0.0012 (11) |
C78 | 0.0295 (14) | 0.0260 (14) | 0.0218 (14) | −0.0037 (11) | 0.0070 (12) | 0.0014 (11) |
C1 | 0.0188 (12) | 0.0241 (13) | 0.0152 (13) | −0.0032 (10) | 0.0017 (10) | 0.0003 (10) |
C5 | 0.0392 (16) | 0.0298 (14) | 0.0230 (15) | −0.0087 (12) | 0.0110 (13) | 0.0009 (11) |
C31 | 0.0231 (13) | 0.0257 (13) | 0.0243 (14) | −0.0006 (10) | 0.0078 (12) | 0.0023 (10) |
C2 | 0.0203 (12) | 0.0272 (14) | 0.0183 (14) | −0.0019 (10) | 0.0023 (11) | −0.0006 (10) |
C39 | 0.0197 (13) | 0.0317 (16) | 0.0262 (15) | −0.0008 (11) | 0.0052 (12) | −0.0053 (11) |
C45 | 0.0306 (15) | 0.0373 (16) | 0.0402 (19) | −0.0062 (13) | 0.0092 (14) | −0.0088 (13) |
C10 | 0.0224 (13) | 0.0304 (15) | 0.0245 (15) | 0.0048 (11) | 0.0098 (12) | 0.0040 (11) |
C41 | 0.0313 (16) | 0.0521 (19) | 0.0265 (17) | −0.0053 (14) | 0.0003 (14) | −0.0045 (14) |
C22 | 0.049 (2) | 0.0440 (18) | 0.0345 (19) | 0.0098 (15) | 0.0105 (16) | −0.0087 (14) |
C34 | 0.0351 (16) | 0.0293 (15) | 0.0410 (19) | 0.0127 (13) | 0.0075 (14) | −0.0031 (13) |
C20 | 0.0271 (13) | 0.0218 (13) | 0.0343 (16) | 0.0031 (11) | 0.0084 (13) | 0.0031 (11) |
C3 | 0.0267 (14) | 0.0332 (15) | 0.0226 (15) | −0.0037 (11) | 0.0101 (12) | −0.0027 (11) |
C84 | 0.0374 (17) | 0.0404 (17) | 0.043 (2) | 0.0016 (14) | −0.0026 (16) | 0.0007 (15) |
C95 | 0.0293 (15) | 0.0413 (18) | 0.0253 (16) | −0.0039 (12) | 0.0067 (13) | 0.0071 (13) |
C30 | 0.0199 (12) | 0.0196 (12) | 0.0228 (14) | 0.0016 (9) | 0.0083 (11) | 0.0019 (10) |
C61 | 0.0388 (17) | 0.0304 (15) | 0.0340 (18) | −0.0125 (13) | 0.0013 (14) | −0.0046 (12) |
C32 | 0.0222 (14) | 0.0351 (15) | 0.0336 (18) | 0.0058 (12) | 0.0010 (13) | 0.0023 (13) |
C68 | 0.0377 (16) | 0.0274 (14) | 0.0248 (16) | −0.0080 (12) | 0.0066 (13) | −0.0043 (11) |
C70 | 0.052 (2) | 0.0402 (18) | 0.0320 (18) | 0.0016 (15) | 0.0048 (16) | 0.0045 (14) |
C105 | 0.069 (2) | 0.0330 (17) | 0.0370 (19) | 0.0062 (16) | 0.0113 (19) | −0.0032 (14) |
C9 | 0.0238 (13) | 0.0234 (13) | 0.0182 (14) | −0.0034 (10) | 0.0012 (11) | −0.0019 (10) |
C91 | 0.051 (2) | 0.050 (2) | 0.0352 (19) | −0.0044 (16) | 0.0190 (17) | −0.0098 (15) |
C16 | 0.0256 (15) | 0.052 (2) | 0.0330 (18) | 0.0080 (13) | 0.0051 (14) | 0.0037 (14) |
C60 | 0.0296 (14) | 0.0211 (13) | 0.0260 (15) | −0.0041 (11) | 0.0046 (12) | −0.0013 (11) |
C36 | 0.0348 (16) | 0.0247 (14) | 0.0344 (17) | 0.0049 (12) | 0.0073 (14) | −0.0069 (12) |
C88 | 0.0367 (17) | 0.0413 (17) | 0.0259 (16) | −0.0034 (13) | 0.0046 (14) | −0.0058 (13) |
C12 | 0.0346 (16) | 0.0279 (15) | 0.0335 (17) | 0.0064 (12) | 0.0063 (14) | −0.0003 (12) |
C65 | 0.0398 (17) | 0.0336 (16) | 0.0306 (17) | −0.0101 (13) | 0.0098 (14) | 0.0059 (13) |
C80 | 0.0429 (19) | 0.053 (2) | 0.040 (2) | 0.0011 (16) | 0.0128 (17) | −0.0131 (16) |
C98 | 0.0259 (15) | 0.069 (2) | 0.0321 (18) | −0.0019 (15) | 0.0056 (14) | 0.0089 (16) |
C167 | 0.0252 (13) | 0.0235 (14) | 0.0254 (15) | −0.0012 (10) | 0.0056 (12) | 0.0015 (11) |
C59 | 0.0201 (12) | 0.0160 (12) | 0.0283 (15) | −0.0009 (10) | 0.0055 (11) | 0.0031 (10) |
C26 | 0.0403 (18) | 0.048 (2) | 0.048 (2) | 0.0164 (16) | 0.0010 (17) | 0.0036 (16) |
C7 | 0.0367 (15) | 0.0216 (13) | 0.0234 (15) | −0.0039 (11) | 0.0045 (13) | 0.0032 (10) |
C74 | 0.055 (2) | 0.0456 (19) | 0.039 (2) | 0.0113 (16) | 0.0156 (18) | −0.0002 (16) |
C63 | 0.0423 (17) | 0.0317 (16) | 0.045 (2) | −0.0191 (14) | 0.0092 (16) | 0.0023 (14) |
C102 | 0.0412 (17) | 0.0304 (15) | 0.0315 (17) | 0.0023 (13) | 0.0098 (14) | 0.0034 (12) |
C49 | 0.0294 (14) | 0.0292 (15) | 0.0225 (15) | 0.0053 (11) | 0.0035 (12) | −0.0043 (11) |
C55 | 0.0387 (17) | 0.0398 (18) | 0.0318 (18) | −0.0038 (14) | −0.0008 (15) | −0.0067 (14) |
C51 | 0.053 (2) | 0.0464 (19) | 0.0240 (17) | 0.0122 (16) | 0.0089 (15) | 0.0018 (14) |
Geometric parameters (Å, º) top
Si1—O111 | 1.6485 (18) | C61—C60 | 1.395 (4) |
Si1—O112 | 1.6546 (17) | C61—H62 | 0.93 |
Si1—O110 | 1.6665 (19) | C32—H33 | 0.93 |
Si1—S114 | 2.0231 (9) | C68—C70 | 1.520 (5) |
O112—C59 | 1.390 (3) | C68—C60 | 1.525 (4) |
O110—C1 | 1.390 (3) | C68—C74 | 1.527 (4) |
O111—C30 | 1.376 (3) | C68—H69 | 0.98 |
N109—C102 | 1.491 (4) | C70—H71 | 0.96 |
N109—C88 | 1.508 (4) | C70—H72 | 0.96 |
N109—C95 | 1.510 (4) | C70—H73 | 0.96 |
N109—H115 | 0.90 (4) | C105—C102 | 1.507 (5) |
C38—C36 | 1.397 (4) | C105—H106 | 0.96 |
C38—C30 | 1.407 (4) | C105—H107 | 0.96 |
C38—C49 | 1.521 (4) | C105—H108 | 0.96 |
C78—C167 | 1.516 (4) | C9—C7 | 1.394 (4) |
C78—C84 | 1.526 (4) | C91—C88 | 1.502 (5) |
C78—C80 | 1.527 (4) | C91—H92 | 0.96 |
C78—H79 | 0.98 | C91—H93 | 0.96 |
C1—C2 | 1.397 (4) | C91—H94 | 0.96 |
C1—C9 | 1.408 (4) | C16—H17 | 0.96 |
C5—C3 | 1.375 (4) | C16—H18 | 0.96 |
C5—C7 | 1.388 (4) | C16—H19 | 0.96 |
C5—H6 | 0.93 | C60—C59 | 1.404 (4) |
C31—C32 | 1.387 (4) | C36—H37 | 0.93 |
C31—C30 | 1.408 (4) | C88—H89 | 0.97 |
C31—C39 | 1.530 (4) | C88—H90 | 0.97 |
C2—C3 | 1.404 (4) | C12—H13 | 0.96 |
C2—C10 | 1.519 (4) | C12—H14 | 0.96 |
C39—C41 | 1.527 (5) | C12—H15 | 0.96 |
C39—C45 | 1.529 (4) | C65—C63 | 1.382 (5) |
C39—H40 | 0.98 | C65—C167 | 1.397 (4) |
C45—H46 | 0.96 | C65—H66 | 0.93 |
C45—H47 | 0.96 | C80—H81 | 0.96 |
C45—H48 | 0.96 | C80—H82 | 0.96 |
C10—C16 | 1.531 (4) | C80—H83 | 0.96 |
C10—C12 | 1.534 (4) | C98—H99 | 0.96 |
C10—H11 | 0.98 | C98—H100 | 0.96 |
C41—H42 | 0.96 | C98—H101 | 0.96 |
C41—H43 | 0.96 | C167—C59 | 1.405 (4) |
C41—H44 | 0.96 | C26—H27 | 0.96 |
C22—C20 | 1.525 (5) | C26—H28 | 0.96 |
C22—H23 | 0.96 | C26—H29 | 0.96 |
C22—H24 | 0.96 | C7—H8 | 0.93 |
C22—H25 | 0.96 | C74—H75 | 0.96 |
C34—C36 | 1.374 (5) | C74—H76 | 0.96 |
C34—C32 | 1.392 (4) | C74—H77 | 0.96 |
C34—H35 | 0.93 | C63—H64 | 0.93 |
C20—C9 | 1.515 (4) | C102—H103 | 0.97 |
C20—C26 | 1.522 (4) | C102—H104 | 0.97 |
C20—H21 | 0.98 | C49—C55 | 1.529 (4) |
C3—H4 | 0.93 | C49—C51 | 1.543 (4) |
C84—H85 | 0.96 | C49—H50 | 0.98 |
C84—H86 | 0.96 | C55—H56 | 0.96 |
C84—H87 | 0.96 | C55—H57 | 0.96 |
C95—C98 | 1.514 (4) | C55—H58 | 0.96 |
C95—H96 | 0.97 | C51—H52 | 0.96 |
C95—H97 | 0.97 | C51—H53 | 0.96 |
C61—C63 | 1.379 (5) | C51—H54 | 0.96 |
| | | |
O111—Si1—O112 | 100.71 (9) | H71—C70—H72 | 109.5 |
O111—Si1—O110 | 106.43 (9) | C68—C70—H73 | 109.5 |
O112—Si1—O110 | 106.25 (10) | H71—C70—H73 | 109.5 |
O111—Si1—S114 | 117.35 (8) | H72—C70—H73 | 109.5 |
O112—Si1—S114 | 114.00 (8) | C102—C105—H106 | 109.5 |
O110—Si1—S114 | 111.04 (7) | C102—C105—H107 | 109.5 |
C59—O112—Si1 | 130.72 (16) | H106—C105—H107 | 109.5 |
C1—O110—Si1 | 129.86 (16) | C102—C105—H108 | 109.5 |
C30—O111—Si1 | 139.68 (16) | H106—C105—H108 | 109.5 |
C102—N109—C88 | 112.0 (2) | H107—C105—H108 | 109.5 |
C102—N109—C95 | 114.1 (2) | C7—C9—C1 | 118.4 (2) |
C88—N109—C95 | 110.9 (2) | C7—C9—C20 | 120.6 (2) |
C102—N109—H115 | 110 (2) | C1—C9—C20 | 120.9 (2) |
C88—N109—H115 | 106 (2) | C88—C91—H92 | 109.5 |
C95—N109—H115 | 103 (2) | C88—C91—H93 | 109.5 |
C36—C38—C30 | 117.0 (3) | H92—C91—H93 | 109.5 |
C36—C38—C49 | 119.5 (2) | C88—C91—H94 | 109.5 |
C30—C38—C49 | 123.4 (2) | H92—C91—H94 | 109.5 |
C167—C78—C84 | 110.3 (2) | H93—C91—H94 | 109.5 |
C167—C78—C80 | 112.7 (2) | C10—C16—H17 | 109.5 |
C84—C78—C80 | 110.2 (3) | C10—C16—H18 | 109.5 |
C167—C78—H79 | 107.8 | H17—C16—H18 | 109.5 |
C84—C78—H79 | 107.8 | C10—C16—H19 | 109.5 |
C80—C78—H79 | 107.8 | H17—C16—H19 | 109.5 |
O110—C1—C2 | 120.5 (2) | H18—C16—H19 | 109.5 |
O110—C1—C9 | 118.0 (2) | C61—C60—C59 | 117.8 (3) |
C2—C1—C9 | 121.4 (2) | C61—C60—C68 | 119.6 (3) |
C3—C5—C7 | 119.8 (3) | C59—C60—C68 | 122.5 (2) |
C3—C5—H6 | 120.1 | C34—C36—C38 | 122.6 (3) |
C7—C5—H6 | 120.1 | C34—C36—H37 | 118.7 |
C32—C31—C30 | 118.5 (3) | C38—C36—H37 | 118.7 |
C32—C31—C39 | 120.9 (3) | C91—C88—N109 | 113.3 (3) |
C30—C31—C39 | 120.5 (2) | C91—C88—H89 | 108.9 |
C1—C2—C3 | 117.9 (2) | N109—C88—H89 | 108.9 |
C1—C2—C10 | 123.2 (2) | C91—C88—H90 | 108.9 |
C3—C2—C10 | 118.9 (2) | N109—C88—H90 | 108.9 |
C41—C39—C45 | 110.3 (2) | H89—C88—H90 | 107.7 |
C41—C39—C31 | 113.0 (2) | C10—C12—H13 | 109.5 |
C45—C39—C31 | 109.8 (2) | C10—C12—H14 | 109.5 |
C41—C39—H40 | 107.8 | H13—C12—H14 | 109.5 |
C45—C39—H40 | 107.8 | C10—C12—H15 | 109.5 |
C31—C39—H40 | 107.8 | H13—C12—H15 | 109.5 |
C39—C45—H46 | 109.5 | H14—C12—H15 | 109.5 |
C39—C45—H47 | 109.5 | C63—C65—C167 | 121.6 (3) |
H46—C45—H47 | 109.5 | C63—C65—H66 | 119.2 |
C39—C45—H48 | 109.5 | C167—C65—H66 | 119.2 |
H46—C45—H48 | 109.5 | C78—C80—H81 | 109.5 |
H47—C45—H48 | 109.5 | C78—C80—H82 | 109.5 |
C2—C10—C16 | 112.0 (2) | H81—C80—H82 | 109.5 |
C2—C10—C12 | 110.4 (2) | C78—C80—H83 | 109.5 |
C16—C10—C12 | 110.6 (2) | H81—C80—H83 | 109.5 |
C2—C10—H11 | 107.9 | H82—C80—H83 | 109.5 |
C16—C10—H11 | 107.9 | C95—C98—H99 | 109.5 |
C12—C10—H11 | 107.9 | C95—C98—H100 | 109.5 |
C39—C41—H42 | 109.5 | H99—C98—H100 | 109.5 |
C39—C41—H43 | 109.5 | C95—C98—H101 | 109.5 |
H42—C41—H43 | 109.5 | H99—C98—H101 | 109.5 |
C39—C41—H44 | 109.5 | H100—C98—H101 | 109.5 |
H42—C41—H44 | 109.5 | C65—C167—C59 | 117.8 (3) |
H43—C41—H44 | 109.5 | C65—C167—C78 | 119.1 (2) |
C20—C22—H23 | 109.5 | C59—C167—C78 | 123.0 (2) |
C20—C22—H24 | 109.5 | O112—C59—C60 | 118.8 (2) |
H23—C22—H24 | 109.5 | O112—C59—C167 | 119.5 (2) |
C20—C22—H25 | 109.5 | C60—C59—C167 | 121.6 (2) |
H23—C22—H25 | 109.5 | C20—C26—H27 | 109.5 |
H24—C22—H25 | 109.5 | C20—C26—H28 | 109.5 |
C36—C34—C32 | 119.2 (3) | H27—C26—H28 | 109.5 |
C36—C34—H35 | 120.4 | C20—C26—H29 | 109.5 |
C32—C34—H35 | 120.4 | H27—C26—H29 | 109.5 |
C9—C20—C26 | 113.7 (3) | H28—C26—H29 | 109.5 |
C9—C20—C22 | 110.3 (2) | C5—C7—C9 | 121.0 (3) |
C26—C20—C22 | 109.9 (3) | C5—C7—H8 | 119.5 |
C9—C20—H21 | 107.5 | C9—C7—H8 | 119.5 |
C26—C20—H21 | 107.5 | C68—C74—H75 | 109.5 |
C22—C20—H21 | 107.5 | C68—C74—H76 | 109.5 |
C5—C3—C2 | 121.6 (3) | H75—C74—H76 | 109.5 |
C5—C3—H4 | 119.2 | C68—C74—H77 | 109.5 |
C2—C3—H4 | 119.2 | H75—C74—H77 | 109.5 |
C78—C84—H85 | 109.5 | H76—C74—H77 | 109.5 |
C78—C84—H86 | 109.5 | C61—C63—C65 | 119.5 (3) |
H85—C84—H86 | 109.5 | C61—C63—H64 | 120.3 |
C78—C84—H87 | 109.5 | C65—C63—H64 | 120.3 |
H85—C84—H87 | 109.5 | N109—C102—C105 | 112.3 (3) |
H86—C84—H87 | 109.5 | N109—C102—H103 | 109.1 |
N109—C95—C98 | 113.7 (2) | C105—C102—H103 | 109.1 |
N109—C95—H96 | 108.8 | N109—C102—H104 | 109.1 |
C98—C95—H96 | 108.8 | C105—C102—H104 | 109.1 |
N109—C95—H97 | 108.8 | H103—C102—H104 | 107.9 |
C98—C95—H97 | 108.8 | C38—C49—C55 | 112.5 (2) |
H96—C95—H97 | 107.7 | C38—C49—C51 | 110.9 (3) |
O111—C30—C38 | 120.2 (2) | C55—C49—C51 | 109.0 (3) |
O111—C30—C31 | 118.0 (2) | C38—C49—H50 | 108.1 |
C38—C30—C31 | 121.6 (2) | C55—C49—H50 | 108.1 |
C63—C61—C60 | 121.7 (3) | C51—C49—H50 | 108.1 |
C63—C61—H62 | 119.1 | C49—C55—H56 | 109.5 |
C60—C61—H62 | 119.1 | C49—C55—H57 | 109.5 |
C31—C32—C34 | 121.1 (3) | H56—C55—H57 | 109.5 |
C31—C32—H33 | 119.4 | C49—C55—H58 | 109.5 |
C34—C32—H33 | 119.4 | H56—C55—H58 | 109.5 |
C70—C68—C60 | 112.3 (3) | H57—C55—H58 | 109.5 |
C70—C68—C74 | 110.4 (3) | C49—C51—H52 | 109.5 |
C60—C68—C74 | 109.9 (2) | C49—C51—H53 | 109.5 |
C70—C68—H69 | 108 | H52—C51—H53 | 109.5 |
C60—C68—H69 | 108 | C49—C51—H54 | 109.5 |
C74—C68—H69 | 108 | H52—C51—H54 | 109.5 |
C68—C70—H71 | 109.5 | H53—C51—H54 | 109.5 |
C68—C70—H72 | 109.5 | | |
| | | |
O111—Si1—O112—C59 | −16.9 (2) | C2—C1—C9—C20 | 177.6 (3) |
O110—Si1—O112—C59 | 93.9 (2) | C26—C20—C9—C7 | −36.6 (4) |
S114—Si1—O112—C59 | −143.5 (2) | C22—C20—C9—C7 | 87.5 (3) |
O111—Si1—O110—C1 | −134.4 (2) | C26—C20—C9—C1 | 145.9 (3) |
O112—Si1—O110—C1 | 118.9 (2) | C22—C20—C9—C1 | −90.0 (3) |
S114—Si1—O110—C1 | −5.6 (2) | C63—C61—C60—C59 | 0.2 (5) |
O112—Si1—O111—C30 | 165.9 (3) | C63—C61—C60—C68 | −177.6 (3) |
O110—Si1—O111—C30 | 55.3 (3) | C70—C68—C60—C61 | −57.9 (4) |
S114—Si1—O111—C30 | −69.8 (3) | C74—C68—C60—C61 | 65.5 (4) |
Si1—O110—C1—C2 | −77.9 (3) | C70—C68—C60—C59 | 124.5 (3) |
Si1—O110—C1—C9 | 105.7 (2) | C74—C68—C60—C59 | −112.2 (3) |
O110—C1—C2—C3 | −176.7 (2) | C32—C34—C36—C38 | −1.0 (5) |
C9—C1—C2—C3 | −0.4 (4) | C30—C38—C36—C34 | 0.0 (4) |
O110—C1—C2—C10 | 0.7 (4) | C49—C38—C36—C34 | 179.2 (3) |
C9—C1—C2—C10 | 176.9 (3) | C102—N109—C88—C91 | 69.2 (3) |
C32—C31—C39—C41 | −31.1 (4) | C95—N109—C88—C91 | −162.0 (3) |
C30—C31—C39—C41 | 152.7 (3) | C63—C65—C167—C59 | −1.1 (5) |
C32—C31—C39—C45 | 92.6 (3) | C63—C65—C167—C78 | 175.8 (3) |
C30—C31—C39—C45 | −83.6 (3) | C84—C78—C167—C65 | −68.9 (3) |
C1—C2—C10—C16 | 129.6 (3) | C80—C78—C167—C65 | 54.7 (4) |
C3—C2—C10—C16 | −53.0 (3) | C84—C78—C167—C59 | 107.8 (3) |
C1—C2—C10—C12 | −106.7 (3) | C80—C78—C167—C59 | −128.6 (3) |
C3—C2—C10—C12 | 70.7 (3) | Si1—O112—C59—C60 | −103.6 (3) |
C7—C5—C3—C2 | −0.3 (4) | Si1—O112—C59—C167 | 80.9 (3) |
C1—C2—C3—C5 | 0.6 (4) | C61—C60—C59—O112 | −177.1 (3) |
C10—C2—C3—C5 | −176.9 (3) | C68—C60—C59—O112 | 0.6 (4) |
C102—N109—C95—C98 | 59.2 (4) | C61—C60—C59—C167 | −1.8 (4) |
C88—N109—C95—C98 | −68.4 (3) | C68—C60—C59—C167 | 175.9 (3) |
Si1—O111—C30—C38 | 90.1 (3) | C65—C167—C59—O112 | 177.5 (2) |
Si1—O111—C30—C31 | −95.4 (3) | C78—C167—C59—O112 | 0.8 (4) |
C36—C38—C30—O111 | 175.7 (2) | C65—C167—C59—C60 | 2.2 (4) |
C49—C38—C30—O111 | −3.5 (4) | C78—C167—C59—C60 | −174.5 (3) |
C36—C38—C30—C31 | 1.4 (4) | C3—C5—C7—C9 | −0.1 (4) |
C49—C38—C30—C31 | −177.8 (2) | C1—C9—C7—C5 | 0.3 (4) |
C32—C31—C30—O111 | −176.0 (2) | C20—C9—C7—C5 | −177.3 (3) |
C39—C31—C30—O111 | 0.3 (4) | C60—C61—C63—C65 | 0.9 (5) |
C32—C31—C30—C38 | −1.6 (4) | C167—C65—C63—C61 | −0.5 (5) |
C39—C31—C30—C38 | 174.7 (2) | C88—N109—C102—C105 | −173.4 (3) |
C30—C31—C32—C34 | 0.5 (4) | C95—N109—C102—C105 | 59.5 (4) |
C39—C31—C32—C34 | −175.8 (3) | C36—C38—C49—C55 | 68.5 (3) |
C36—C34—C32—C31 | 0.8 (5) | C30—C38—C49—C55 | −112.4 (3) |
O110—C1—C9—C7 | 176.4 (2) | C36—C38—C49—C51 | −53.9 (4) |
C2—C1—C9—C7 | 0.0 (4) | C30—C38—C49—C51 | 125.2 (3) |
O110—C1—C9—C20 | −6.1 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N109—H115···S114 | 0.90 (4) | 2.19 (4) | 3.086 (3) | 169 (3) |
Crystal data top
C36H51O3SSi·C6H16N | F(000) = 1520 |
Mr = 694.11 | Dx = 1.107 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 2579 reflections |
a = 11.7030 (12) Å | θ = 3.1–29.4° |
b = 17.9455 (13) Å | µ = 0.14 mm−1 |
c = 20.2104 (19) Å | T = 180 K |
β = 101.001 (8)° | Block, colourless |
V = 4166.5 (7) Å3 | 0.34 × 0.22 × 0.13 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 7008 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.053 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.2° |
rotation method scans | h = −14→14 |
20391 measured reflections | k = −19→22 |
7996 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 0.98 | Δρmax = 0.28 e Å−3 |
7996 reflections | Δρmin = −0.18 e Å−3 |
452 parameters | Absolute structure: Flack x determined using 3042 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
Si1 | 0.55632 (5) | 0.26175 (4) | 0.06094 (4) | 0.01747 (15) | |
S114 | 0.40862 (6) | 0.20915 (4) | 0.01665 (4) | 0.02615 (16) | |
O112 | 0.54750 (16) | 0.35373 (9) | 0.05785 (10) | 0.0220 (4) | |
O110 | 0.59240 (15) | 0.23942 (10) | 0.14228 (9) | 0.0214 (4) | |
O111 | 0.67359 (16) | 0.24802 (10) | 0.02831 (10) | 0.0223 (4) | |
N109 | 0.1976 (2) | 0.28338 (14) | −0.07437 (13) | 0.0282 (5) | |
H115 | 0.265 (3) | 0.2656 (16) | −0.0512 (16) | 0.017 (7)* | |
C38 | 0.7314 (2) | 0.14413 (15) | −0.03299 (15) | 0.0255 (6) | |
C78 | 0.5838 (3) | 0.38514 (16) | −0.07811 (15) | 0.0282 (6) | |
H79 | 0.5391 | 0.3439 | −0.0639 | 0.034* | |
C1 | 0.5327 (2) | 0.19667 (14) | 0.18188 (13) | 0.0210 (5) | |
C5 | 0.4249 (3) | 0.11152 (17) | 0.26696 (16) | 0.0329 (7) | |
H6 | 0.3887 | 0.083 | 0.2954 | 0.039* | |
C31 | 0.8564 (2) | 0.19032 (16) | 0.07033 (15) | 0.0259 (6) | |
C2 | 0.4388 (2) | 0.22663 (15) | 0.20639 (14) | 0.0243 (6) | |
C39 | 0.8811 (2) | 0.24776 (16) | 0.12708 (16) | 0.0288 (6) | |
H40 | 0.8068 | 0.2606 | 0.1397 | 0.035* | |
C45 | 0.9309 (3) | 0.31891 (18) | 0.10153 (19) | 0.0383 (7) | |
H46 | 1.0048 | 0.3081 | 0.0896 | 0.057* | |
H47 | 0.941 | 0.3561 | 0.1363 | 0.057* | |
H48 | 0.8781 | 0.3371 | 0.0626 | 0.057* | |
C10 | 0.3953 (2) | 0.30564 (16) | 0.19133 (15) | 0.0273 (6) | |
H11 | 0.4334 | 0.3257 | 0.156 | 0.033* | |
C41 | 0.9621 (3) | 0.2190 (2) | 0.18988 (18) | 0.0413 (8) | |
H42 | 0.9314 | 0.1735 | 0.2044 | 0.062* | |
H43 | 0.9682 | 0.2556 | 0.2251 | 0.062* | |
H44 | 1.0377 | 0.2098 | 0.1798 | 0.062* | |
C22 | 0.6245 (3) | 0.0487 (2) | 0.10569 (19) | 0.0474 (9) | |
H23 | 0.584 | 0.0051 | 0.1161 | 0.071* | |
H24 | 0.6875 | 0.0343 | 0.0842 | 0.071* | |
H25 | 0.5717 | 0.0803 | 0.0759 | 0.071* | |
C34 | 0.9205 (3) | 0.08789 (17) | 0.00836 (18) | 0.0381 (7) | |
H35 | 0.9764 | 0.0524 | 0.0038 | 0.046* | |
C20 | 0.6723 (3) | 0.09078 (15) | 0.17032 (16) | 0.0293 (6) | |
H21 | 0.7193 | 0.1321 | 0.1585 | 0.035* | |
C3 | 0.3857 (2) | 0.18219 (17) | 0.24927 (15) | 0.0292 (6) | |
H4 | 0.3228 | 0.2011 | 0.266 | 0.035* | |
C84 | 0.4982 (3) | 0.4393 (2) | −0.1193 (2) | 0.0460 (8) | |
H85 | 0.5394 | 0.4823 | −0.1304 | 0.069* | |
H86 | 0.4413 | 0.4542 | −0.0934 | 0.069* | |
H87 | 0.4599 | 0.4153 | −0.16 | 0.069* | |
C95 | 0.1072 (3) | 0.24943 (18) | −0.03943 (17) | 0.0350 (7) | |
H96 | 0.1244 | 0.2635 | 0.0078 | 0.042* | |
H97 | 0.1125 | 0.1956 | −0.0417 | 0.042* | |
C30 | 0.7521 (2) | 0.19247 (14) | 0.02268 (14) | 0.0221 (6) | |
C61 | 0.7623 (3) | 0.50374 (18) | 0.09641 (18) | 0.0389 (8) | |
H62 | 0.7998 | 0.5312 | 0.1333 | 0.047* | |
C32 | 0.9390 (3) | 0.13732 (17) | 0.06262 (16) | 0.0335 (7) | |
H33 | 1.0079 | 0.1346 | 0.0942 | 0.04* | |
C68 | 0.6578 (3) | 0.43506 (17) | 0.17623 (16) | 0.0329 (7) | |
H69 | 0.6049 | 0.3924 | 0.1739 | 0.04* | |
C70 | 0.7669 (3) | 0.4176 (2) | 0.22819 (19) | 0.0468 (9) | |
H71 | 0.8038 | 0.374 | 0.2145 | 0.07* | |
H72 | 0.746 | 0.4089 | 0.2712 | 0.07* | |
H73 | 0.8196 | 0.459 | 0.2316 | 0.07* | |
C105 | 0.2251 (4) | 0.3978 (2) | −0.0037 (2) | 0.0517 (10) | |
H106 | 0.2392 | 0.4504 | −0.0057 | 0.078* | |
H107 | 0.2925 | 0.3739 | 0.0221 | 0.078* | |
H108 | 0.1594 | 0.3894 | 0.0174 | 0.078* | |
C9 | 0.5738 (2) | 0.12421 (15) | 0.19941 (14) | 0.0240 (6) | |
C91 | 0.2945 (4) | 0.2637 (2) | −0.1740 (2) | 0.0489 (9) | |
H92 | 0.2861 | 0.2381 | −0.2163 | 0.073* | |
H93 | 0.3609 | 0.2443 | −0.1434 | 0.073* | |
H94 | 0.3053 | 0.3159 | −0.1808 | 0.073* | |
C16 | 0.2636 (3) | 0.3082 (2) | 0.16539 (18) | 0.0410 (8) | |
H17 | 0.2424 | 0.2715 | 0.1306 | 0.061* | |
H18 | 0.2419 | 0.3568 | 0.1474 | 0.061* | |
H19 | 0.224 | 0.2979 | 0.2018 | 0.061* | |
C60 | 0.6841 (3) | 0.44782 (14) | 0.10624 (16) | 0.0276 (6) | |
C36 | 0.8190 (3) | 0.09230 (17) | −0.03809 (17) | 0.0342 (7) | |
H37 | 0.8077 | 0.0596 | −0.0745 | 0.041* | |
C88 | 0.1869 (3) | 0.25213 (19) | −0.14472 (17) | 0.0387 (8) | |
H89 | 0.1707 | 0.1992 | −0.1437 | 0.046* | |
H90 | 0.1214 | 0.2757 | −0.1739 | 0.046* | |
C12 | 0.4290 (3) | 0.35503 (17) | 0.25402 (17) | 0.0355 (7) | |
H13 | 0.3919 | 0.3368 | 0.2892 | 0.053* | |
H14 | 0.4044 | 0.4053 | 0.243 | 0.053* | |
H15 | 0.512 | 0.3539 | 0.269 | 0.053* | |
C65 | 0.7288 (3) | 0.47959 (18) | −0.02156 (17) | 0.0370 (7) | |
H66 | 0.7441 | 0.4907 | −0.064 | 0.044* | |
C80 | 0.6646 (3) | 0.3530 (2) | −0.1215 (2) | 0.0491 (9) | |
H81 | 0.6197 | 0.3258 | −0.1585 | 0.074* | |
H82 | 0.7196 | 0.32 | −0.0948 | 0.074* | |
H83 | 0.7055 | 0.3927 | −0.1386 | 0.074* | |
C98 | −0.0158 (3) | 0.2728 (2) | −0.0691 (2) | 0.0483 (9) | |
H99 | −0.0318 | 0.2626 | −0.1166 | 0.072* | |
H100 | −0.0247 | 0.3251 | −0.0619 | 0.072* | |
H101 | −0.0693 | 0.2454 | −0.0478 | 0.072* | |
C167 | 0.6491 (2) | 0.42328 (15) | −0.01527 (15) | 0.0263 (6) | |
C59 | 0.6293 (2) | 0.40719 (14) | 0.04964 (15) | 0.0228 (6) | |
C26 | 0.7528 (3) | 0.0406 (2) | 0.2192 (2) | 0.0518 (10) | |
H27 | 0.7119 | −0.0039 | 0.2271 | 0.078* | |
H28 | 0.778 | 0.0664 | 0.261 | 0.078* | |
H29 | 0.8193 | 0.0276 | 0.2002 | 0.078* | |
C7 | 0.5184 (3) | 0.08276 (16) | 0.24241 (15) | 0.0306 (6) | |
H8 | 0.5447 | 0.0349 | 0.2548 | 0.037* | |
C74 | 0.5966 (4) | 0.5028 (2) | 0.1984 (2) | 0.0519 (10) | |
H75 | 0.5802 | 0.4942 | 0.2425 | 0.078* | |
H76 | 0.5251 | 0.5113 | 0.1671 | 0.078* | |
H77 | 0.646 | 0.5457 | 0.1995 | 0.078* | |
C63 | 0.7854 (3) | 0.51912 (19) | 0.03358 (18) | 0.0428 (8) | |
H64 | 0.8388 | 0.556 | 0.0283 | 0.051* | |
C102 | 0.2003 (3) | 0.36622 (18) | −0.07404 (17) | 0.0381 (7) | |
H103 | 0.1258 | 0.3849 | −0.0977 | 0.046* | |
H104 | 0.2596 | 0.3832 | −0.0981 | 0.046* | |
C49 | 0.6222 (3) | 0.14619 (16) | −0.08721 (15) | 0.0299 (6) | |
H50 | 0.5762 | 0.1896 | −0.0788 | 0.036* | |
C55 | 0.5465 (3) | 0.07691 (19) | −0.08671 (19) | 0.0422 (8) | |
H56 | 0.5894 | 0.0336 | −0.0954 | 0.063* | |
H57 | 0.4777 | 0.0815 | −0.121 | 0.063* | |
H58 | 0.5247 | 0.0721 | −0.0434 | 0.063* | |
C51 | 0.6524 (4) | 0.1550 (2) | −0.15779 (18) | 0.0456 (8) | |
H52 | 0.701 | 0.198 | −0.1583 | 0.068* | |
H53 | 0.5821 | 0.161 | −0.1906 | 0.068* | |
H54 | 0.6931 | 0.1115 | −0.1683 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0163 (3) | 0.0178 (3) | 0.0188 (4) | −0.0003 (3) | 0.0046 (3) | 0.0001 (3) |
S114 | 0.0208 (3) | 0.0225 (3) | 0.0328 (4) | −0.0040 (3) | −0.0008 (3) | 0.0002 (3) |
O112 | 0.0206 (9) | 0.0209 (9) | 0.0250 (10) | −0.0025 (8) | 0.0057 (8) | −0.0003 (8) |
O110 | 0.0200 (9) | 0.0237 (9) | 0.0210 (10) | −0.0009 (7) | 0.0052 (8) | 0.0029 (7) |
O111 | 0.0211 (9) | 0.0223 (9) | 0.0250 (11) | 0.0019 (7) | 0.0085 (8) | −0.0004 (7) |
N109 | 0.0243 (12) | 0.0347 (14) | 0.0246 (14) | 0.0008 (10) | 0.0019 (11) | 0.0039 (10) |
C38 | 0.0281 (14) | 0.0243 (13) | 0.0251 (15) | 0.0005 (11) | 0.0076 (12) | 0.0014 (11) |
C78 | 0.0328 (15) | 0.0270 (14) | 0.0259 (16) | −0.0049 (12) | 0.0080 (13) | 0.0020 (11) |
C1 | 0.0203 (12) | 0.0258 (13) | 0.0165 (13) | −0.0041 (10) | 0.0023 (11) | −0.0004 (10) |
C5 | 0.0427 (17) | 0.0325 (15) | 0.0264 (16) | −0.0105 (13) | 0.0140 (14) | 0.0015 (12) |
C31 | 0.0240 (13) | 0.0296 (14) | 0.0255 (15) | −0.0003 (11) | 0.0083 (12) | 0.0022 (11) |
C2 | 0.0228 (13) | 0.0303 (14) | 0.0191 (14) | −0.0027 (11) | 0.0026 (12) | −0.0013 (11) |
C39 | 0.0210 (13) | 0.0370 (17) | 0.0290 (16) | −0.0022 (11) | 0.0060 (12) | −0.0054 (12) |
C45 | 0.0316 (15) | 0.0375 (17) | 0.047 (2) | −0.0060 (13) | 0.0097 (15) | −0.0093 (14) |
C10 | 0.0241 (14) | 0.0344 (16) | 0.0254 (16) | 0.0054 (11) | 0.0101 (12) | 0.0043 (12) |
C41 | 0.0342 (17) | 0.058 (2) | 0.0296 (18) | −0.0056 (15) | 0.0000 (15) | −0.0065 (15) |
C22 | 0.056 (2) | 0.049 (2) | 0.040 (2) | 0.0117 (17) | 0.0139 (18) | −0.0094 (16) |
C34 | 0.0366 (17) | 0.0347 (16) | 0.043 (2) | 0.0146 (14) | 0.0072 (15) | −0.0039 (14) |
C20 | 0.0287 (14) | 0.0230 (14) | 0.0371 (18) | 0.0030 (11) | 0.0086 (13) | 0.0031 (12) |
C3 | 0.0277 (14) | 0.0378 (16) | 0.0245 (16) | −0.0046 (12) | 0.0107 (13) | −0.0026 (12) |
C84 | 0.0409 (18) | 0.0453 (19) | 0.048 (2) | 0.0030 (15) | −0.0021 (17) | −0.0006 (16) |
C95 | 0.0310 (16) | 0.0457 (19) | 0.0284 (18) | −0.0037 (13) | 0.0057 (14) | 0.0092 (13) |
C30 | 0.0217 (13) | 0.0215 (13) | 0.0247 (15) | 0.0011 (10) | 0.0088 (12) | 0.0020 (10) |
C61 | 0.0458 (18) | 0.0309 (16) | 0.038 (2) | −0.0157 (14) | 0.0033 (16) | −0.0055 (13) |
C32 | 0.0241 (14) | 0.0397 (16) | 0.0345 (19) | 0.0081 (12) | −0.0001 (14) | 0.0027 (13) |
C68 | 0.0415 (17) | 0.0301 (15) | 0.0269 (17) | −0.0097 (13) | 0.0057 (14) | −0.0050 (12) |
C70 | 0.057 (2) | 0.045 (2) | 0.037 (2) | 0.0013 (17) | 0.0060 (18) | 0.0048 (15) |
C105 | 0.077 (3) | 0.0365 (18) | 0.041 (2) | 0.0089 (18) | 0.011 (2) | −0.0052 (15) |
C9 | 0.0264 (13) | 0.0243 (13) | 0.0198 (15) | −0.0034 (11) | 0.0008 (12) | −0.0019 (11) |
C91 | 0.057 (2) | 0.056 (2) | 0.039 (2) | −0.0051 (17) | 0.0209 (18) | −0.0114 (16) |
C16 | 0.0272 (16) | 0.058 (2) | 0.038 (2) | 0.0082 (14) | 0.0047 (15) | 0.0039 (16) |
C60 | 0.0298 (14) | 0.0242 (13) | 0.0283 (16) | −0.0045 (12) | 0.0043 (12) | −0.0016 (11) |
C36 | 0.0379 (17) | 0.0274 (15) | 0.0380 (19) | 0.0061 (12) | 0.0087 (15) | −0.0080 (12) |
C88 | 0.0398 (18) | 0.0476 (19) | 0.0277 (18) | −0.0060 (14) | 0.0041 (15) | −0.0057 (14) |
C12 | 0.0379 (17) | 0.0316 (16) | 0.0369 (19) | 0.0078 (13) | 0.0069 (15) | −0.0005 (13) |
C65 | 0.0417 (18) | 0.0355 (17) | 0.0348 (19) | −0.0105 (14) | 0.0097 (15) | 0.0063 (13) |
C80 | 0.048 (2) | 0.058 (2) | 0.043 (2) | 0.0005 (17) | 0.0146 (18) | −0.0134 (17) |
C98 | 0.0294 (16) | 0.080 (3) | 0.035 (2) | −0.0020 (17) | 0.0047 (15) | 0.0112 (18) |
C167 | 0.0281 (14) | 0.0222 (14) | 0.0295 (16) | −0.0013 (11) | 0.0075 (13) | 0.0010 (11) |
C59 | 0.0203 (12) | 0.0175 (12) | 0.0302 (16) | −0.0018 (10) | 0.0041 (12) | 0.0021 (11) |
C26 | 0.044 (2) | 0.052 (2) | 0.056 (3) | 0.0195 (17) | 0.0023 (19) | 0.0047 (18) |
C7 | 0.0398 (16) | 0.0234 (14) | 0.0280 (17) | −0.0034 (12) | 0.0047 (14) | 0.0022 (11) |
C74 | 0.062 (2) | 0.054 (2) | 0.042 (2) | 0.0148 (18) | 0.016 (2) | −0.0015 (17) |
C63 | 0.0457 (19) | 0.0348 (17) | 0.049 (2) | −0.0199 (14) | 0.0125 (17) | 0.0027 (15) |
C102 | 0.0464 (18) | 0.0339 (16) | 0.0358 (19) | 0.0016 (14) | 0.0121 (16) | 0.0015 (13) |
C49 | 0.0326 (15) | 0.0329 (16) | 0.0236 (16) | 0.0054 (12) | 0.0040 (13) | −0.0031 (12) |
C55 | 0.0428 (18) | 0.0429 (19) | 0.038 (2) | −0.0051 (15) | −0.0004 (16) | −0.0058 (15) |
C51 | 0.058 (2) | 0.052 (2) | 0.0282 (19) | 0.0131 (17) | 0.0112 (17) | 0.0007 (15) |
Geometric parameters (Å, º) top
Si1—O111 | 1.6507 (18) | C61—C60 | 1.398 (4) |
Si1—O112 | 1.6542 (18) | C61—H62 | 0.93 |
Si1—O110 | 1.6664 (19) | C32—H33 | 0.93 |
Si1—S114 | 2.0222 (10) | C68—C60 | 1.521 (4) |
O112—C59 | 1.388 (3) | C68—C74 | 1.521 (5) |
O110—C1 | 1.390 (3) | C68—C70 | 1.523 (5) |
O111—C30 | 1.375 (3) | C68—H69 | 0.98 |
N109—C102 | 1.487 (4) | C70—H71 | 0.96 |
N109—C95 | 1.508 (4) | C70—H72 | 0.96 |
N109—C88 | 1.511 (4) | C70—H73 | 0.96 |
N109—H115 | 0.90 (3) | C105—C102 | 1.507 (5) |
C38—C36 | 1.402 (4) | C105—H106 | 0.96 |
C38—C30 | 1.405 (4) | C105—H107 | 0.96 |
C38—C49 | 1.517 (4) | C105—H108 | 0.96 |
C78—C167 | 1.515 (4) | C9—C7 | 1.394 (4) |
C78—C80 | 1.521 (4) | C91—C88 | 1.504 (5) |
C78—C84 | 1.524 (5) | C91—H92 | 0.96 |
C78—H79 | 0.98 | C91—H93 | 0.96 |
C1—C2 | 1.396 (4) | C91—H94 | 0.96 |
C1—C9 | 1.408 (4) | C16—H17 | 0.96 |
C5—C3 | 1.373 (4) | C16—H18 | 0.96 |
C5—C7 | 1.385 (4) | C16—H19 | 0.96 |
C5—H6 | 0.93 | C60—C59 | 1.404 (4) |
C31—C32 | 1.385 (4) | C36—H37 | 0.93 |
C31—C30 | 1.404 (4) | C88—H89 | 0.97 |
C31—C39 | 1.528 (4) | C88—H90 | 0.97 |
C2—C3 | 1.407 (4) | C12—H13 | 0.96 |
C2—C10 | 1.518 (4) | C12—H14 | 0.96 |
C39—C41 | 1.522 (5) | C12—H15 | 0.96 |
C39—C45 | 1.533 (4) | C65—C63 | 1.379 (5) |
C39—H40 | 0.98 | C65—C167 | 1.398 (4) |
C45—H46 | 0.96 | C65—H66 | 0.93 |
C45—H47 | 0.96 | C80—H81 | 0.96 |
C45—H48 | 0.96 | C80—H82 | 0.96 |
C10—C16 | 1.531 (4) | C80—H83 | 0.96 |
C10—C12 | 1.535 (4) | C98—H99 | 0.96 |
C10—H11 | 0.98 | C98—H100 | 0.96 |
C41—H42 | 0.96 | C98—H101 | 0.96 |
C41—H43 | 0.96 | C167—C59 | 1.405 (4) |
C41—H44 | 0.96 | C26—H27 | 0.96 |
C22—C20 | 1.520 (5) | C26—H28 | 0.96 |
C22—H23 | 0.96 | C26—H29 | 0.96 |
C22—H24 | 0.96 | C7—H8 | 0.93 |
C22—H25 | 0.96 | C74—H75 | 0.96 |
C34—C36 | 1.368 (5) | C74—H76 | 0.96 |
C34—C32 | 1.395 (5) | C74—H77 | 0.96 |
C34—H35 | 0.93 | C63—H64 | 0.93 |
C20—C9 | 1.514 (4) | C102—H103 | 0.97 |
C20—C26 | 1.523 (5) | C102—H104 | 0.97 |
C20—H21 | 0.98 | C49—C55 | 1.528 (4) |
C3—H4 | 0.93 | C49—C51 | 1.542 (4) |
C84—H85 | 0.96 | C49—H50 | 0.98 |
C84—H86 | 0.96 | C55—H56 | 0.96 |
C84—H87 | 0.96 | C55—H57 | 0.96 |
C95—C98 | 1.510 (5) | C55—H58 | 0.96 |
C95—H96 | 0.97 | C51—H52 | 0.96 |
C95—H97 | 0.97 | C51—H53 | 0.96 |
C61—C63 | 1.376 (5) | C51—H54 | 0.96 |
| | | |
O111—Si1—O112 | 100.63 (9) | H71—C70—H72 | 109.5 |
O111—Si1—O110 | 106.54 (10) | C68—C70—H73 | 109.5 |
O112—Si1—O110 | 106.23 (10) | H71—C70—H73 | 109.5 |
O111—Si1—S114 | 117.33 (8) | H72—C70—H73 | 109.5 |
O112—Si1—S114 | 114.03 (8) | C102—C105—H106 | 109.5 |
O110—Si1—S114 | 111.02 (7) | C102—C105—H107 | 109.5 |
C59—O112—Si1 | 130.91 (16) | H106—C105—H107 | 109.5 |
C1—O110—Si1 | 129.81 (17) | C102—C105—H108 | 109.5 |
C30—O111—Si1 | 139.54 (17) | H106—C105—H108 | 109.5 |
C102—N109—C95 | 114.7 (2) | H107—C105—H108 | 109.5 |
C102—N109—C88 | 111.9 (2) | C7—C9—C1 | 118.2 (2) |
C95—N109—C88 | 110.5 (2) | C7—C9—C20 | 120.6 (2) |
C102—N109—H115 | 109.8 (18) | C1—C9—C20 | 121.1 (2) |
C95—N109—H115 | 103.9 (19) | C88—C91—H92 | 109.5 |
C88—N109—H115 | 105.4 (19) | C88—C91—H93 | 109.5 |
C36—C38—C30 | 116.9 (3) | H92—C91—H93 | 109.5 |
C36—C38—C49 | 119.3 (3) | C88—C91—H94 | 109.5 |
C30—C38—C49 | 123.8 (2) | H92—C91—H94 | 109.5 |
C167—C78—C80 | 112.7 (3) | H93—C91—H94 | 109.5 |
C167—C78—C84 | 110.1 (3) | C10—C16—H17 | 109.5 |
C80—C78—C84 | 110.1 (3) | C10—C16—H18 | 109.5 |
C167—C78—H79 | 107.9 | H17—C16—H18 | 109.5 |
C80—C78—H79 | 107.9 | C10—C16—H19 | 109.5 |
C84—C78—H79 | 107.9 | H17—C16—H19 | 109.5 |
O110—C1—C2 | 120.5 (2) | H18—C16—H19 | 109.5 |
O110—C1—C9 | 118.0 (2) | C61—C60—C59 | 117.8 (3) |
C2—C1—C9 | 121.4 (2) | C61—C60—C68 | 119.6 (3) |
C3—C5—C7 | 119.9 (3) | C59—C60—C68 | 122.5 (2) |
C3—C5—H6 | 120 | C34—C36—C38 | 122.6 (3) |
C7—C5—H6 | 120 | C34—C36—H37 | 118.7 |
C32—C31—C30 | 118.4 (3) | C38—C36—H37 | 118.7 |
C32—C31—C39 | 120.8 (3) | C91—C88—N109 | 113.1 (3) |
C30—C31—C39 | 120.8 (2) | C91—C88—H89 | 108.9 |
C1—C2—C3 | 118.1 (2) | N109—C88—H89 | 108.9 |
C1—C2—C10 | 123.1 (2) | C91—C88—H90 | 108.9 |
C3—C2—C10 | 118.8 (2) | N109—C88—H90 | 108.9 |
C41—C39—C31 | 113.3 (3) | H89—C88—H90 | 107.8 |
C41—C39—C45 | 110.3 (3) | C10—C12—H13 | 109.5 |
C31—C39—C45 | 109.8 (2) | C10—C12—H14 | 109.5 |
C41—C39—H40 | 107.7 | H13—C12—H14 | 109.5 |
C31—C39—H40 | 107.7 | C10—C12—H15 | 109.5 |
C45—C39—H40 | 107.7 | H13—C12—H15 | 109.5 |
C39—C45—H46 | 109.5 | H14—C12—H15 | 109.5 |
C39—C45—H47 | 109.5 | C63—C65—C167 | 121.6 (3) |
H46—C45—H47 | 109.5 | C63—C65—H66 | 119.2 |
C39—C45—H48 | 109.5 | C167—C65—H66 | 119.2 |
H46—C45—H48 | 109.5 | C78—C80—H81 | 109.5 |
H47—C45—H48 | 109.5 | C78—C80—H82 | 109.5 |
C2—C10—C16 | 112.0 (3) | H81—C80—H82 | 109.5 |
C2—C10—C12 | 110.5 (2) | C78—C80—H83 | 109.5 |
C16—C10—C12 | 110.5 (2) | H81—C80—H83 | 109.5 |
C2—C10—H11 | 107.9 | H82—C80—H83 | 109.5 |
C16—C10—H11 | 107.9 | C95—C98—H99 | 109.5 |
C12—C10—H11 | 107.9 | C95—C98—H100 | 109.5 |
C39—C41—H42 | 109.5 | H99—C98—H100 | 109.5 |
C39—C41—H43 | 109.5 | C95—C98—H101 | 109.5 |
H42—C41—H43 | 109.5 | H99—C98—H101 | 109.5 |
C39—C41—H44 | 109.5 | H100—C98—H101 | 109.5 |
H42—C41—H44 | 109.5 | C65—C167—C59 | 117.7 (3) |
H43—C41—H44 | 109.5 | C65—C167—C78 | 119.3 (3) |
C20—C22—H23 | 109.5 | C59—C167—C78 | 122.9 (2) |
C20—C22—H24 | 109.5 | O112—C59—C60 | 118.7 (2) |
H23—C22—H24 | 109.5 | O112—C59—C167 | 119.6 (2) |
C20—C22—H25 | 109.5 | C60—C59—C167 | 121.6 (2) |
H23—C22—H25 | 109.5 | C20—C26—H27 | 109.5 |
H24—C22—H25 | 109.5 | C20—C26—H28 | 109.5 |
C36—C34—C32 | 119.1 (3) | H27—C26—H28 | 109.5 |
C36—C34—H35 | 120.4 | C20—C26—H29 | 109.5 |
C32—C34—H35 | 120.4 | H27—C26—H29 | 109.5 |
C9—C20—C22 | 110.3 (3) | H28—C26—H29 | 109.5 |
C9—C20—C26 | 113.9 (3) | C5—C7—C9 | 121.2 (3) |
C22—C20—C26 | 110.1 (3) | C5—C7—H8 | 119.4 |
C9—C20—H21 | 107.4 | C9—C7—H8 | 119.4 |
C22—C20—H21 | 107.4 | C68—C74—H75 | 109.5 |
C26—C20—H21 | 107.4 | C68—C74—H76 | 109.5 |
C5—C3—C2 | 121.3 (3) | H75—C74—H76 | 109.5 |
C5—C3—H4 | 119.4 | C68—C74—H77 | 109.5 |
C2—C3—H4 | 119.4 | H75—C74—H77 | 109.5 |
C78—C84—H85 | 109.5 | H76—C74—H77 | 109.5 |
C78—C84—H86 | 109.5 | C61—C63—C65 | 119.6 (3) |
H85—C84—H86 | 109.5 | C61—C63—H64 | 120.2 |
C78—C84—H87 | 109.5 | C65—C63—H64 | 120.2 |
H85—C84—H87 | 109.5 | N109—C102—C105 | 112.4 (3) |
H86—C84—H87 | 109.5 | N109—C102—H103 | 109.1 |
N109—C95—C98 | 113.8 (3) | C105—C102—H103 | 109.1 |
N109—C95—H96 | 108.8 | N109—C102—H104 | 109.1 |
C98—C95—H96 | 108.8 | C105—C102—H104 | 109.1 |
N109—C95—H97 | 108.8 | H103—C102—H104 | 107.9 |
C98—C95—H97 | 108.8 | C38—C49—C55 | 112.7 (3) |
H96—C95—H97 | 107.7 | C38—C49—C51 | 111.1 (3) |
O111—C30—C31 | 118.1 (2) | C55—C49—C51 | 109.0 (3) |
O111—C30—C38 | 119.9 (2) | C38—C49—H50 | 108 |
C31—C30—C38 | 121.8 (2) | C55—C49—H50 | 108 |
C63—C61—C60 | 121.6 (3) | C51—C49—H50 | 108 |
C63—C61—H62 | 119.2 | C49—C55—H56 | 109.5 |
C60—C61—H62 | 119.2 | C49—C55—H57 | 109.5 |
C31—C32—C34 | 121.2 (3) | H56—C55—H57 | 109.5 |
C31—C32—H33 | 119.4 | C49—C55—H58 | 109.5 |
C34—C32—H33 | 119.4 | H56—C55—H58 | 109.5 |
C60—C68—C74 | 110.1 (3) | H57—C55—H58 | 109.5 |
C60—C68—C70 | 112.4 (3) | C49—C51—H52 | 109.5 |
C74—C68—C70 | 109.9 (3) | C49—C51—H53 | 109.5 |
C60—C68—H69 | 108.1 | H52—C51—H53 | 109.5 |
C74—C68—H69 | 108.1 | C49—C51—H54 | 109.5 |
C70—C68—H69 | 108.1 | H52—C51—H54 | 109.5 |
C68—C70—H71 | 109.5 | H53—C51—H54 | 109.5 |
C68—C70—H72 | 109.5 | | |
| | | |
O111—Si1—O112—C59 | −16.9 (3) | C2—C1—C9—C20 | 177.4 (3) |
O110—Si1—O112—C59 | 94.0 (2) | C22—C20—C9—C7 | 86.8 (3) |
S114—Si1—O112—C59 | −143.4 (2) | C26—C20—C9—C7 | −37.7 (4) |
O111—Si1—O110—C1 | −134.2 (2) | C22—C20—C9—C1 | −90.7 (3) |
O112—Si1—O110—C1 | 119.1 (2) | C26—C20—C9—C1 | 144.8 (3) |
S114—Si1—O110—C1 | −5.4 (2) | C63—C61—C60—C59 | 0.2 (5) |
O112—Si1—O111—C30 | 165.6 (3) | C63—C61—C60—C68 | −177.5 (3) |
O110—Si1—O111—C30 | 55.0 (3) | C74—C68—C60—C61 | 65.1 (4) |
S114—Si1—O111—C30 | −70.1 (3) | C70—C68—C60—C61 | −57.8 (4) |
Si1—O110—C1—C2 | −78.1 (3) | C74—C68—C60—C59 | −112.5 (3) |
Si1—O110—C1—C9 | 105.4 (3) | C70—C68—C60—C59 | 124.6 (3) |
O110—C1—C2—C3 | −176.5 (2) | C32—C34—C36—C38 | −0.9 (5) |
C9—C1—C2—C3 | −0.2 (4) | C30—C38—C36—C34 | 0.1 (5) |
O110—C1—C2—C10 | 0.8 (4) | C49—C38—C36—C34 | 179.1 (3) |
C9—C1—C2—C10 | 177.1 (3) | C102—N109—C88—C91 | 69.4 (4) |
C32—C31—C39—C41 | −30.8 (4) | C95—N109—C88—C91 | −161.5 (3) |
C30—C31—C39—C41 | 152.6 (3) | C63—C65—C167—C59 | −0.9 (5) |
C32—C31—C39—C45 | 93.0 (3) | C63—C65—C167—C78 | 176.1 (3) |
C30—C31—C39—C45 | −83.6 (3) | C80—C78—C167—C65 | 54.6 (4) |
C1—C2—C10—C16 | 129.5 (3) | C84—C78—C167—C65 | −68.7 (3) |
C3—C2—C10—C16 | −53.2 (4) | C80—C78—C167—C59 | −128.5 (3) |
C1—C2—C10—C12 | −106.9 (3) | C84—C78—C167—C59 | 108.1 (3) |
C3—C2—C10—C12 | 70.4 (3) | Si1—O112—C59—C60 | −103.8 (3) |
C7—C5—C3—C2 | −0.1 (5) | Si1—O112—C59—C167 | 80.9 (3) |
C1—C2—C3—C5 | 0.3 (4) | C61—C60—C59—O112 | −177.2 (3) |
C10—C2—C3—C5 | −177.1 (3) | C68—C60—C59—O112 | 0.5 (4) |
C102—N109—C95—C98 | 59.2 (4) | C61—C60—C59—C167 | −2.0 (4) |
C88—N109—C95—C98 | −68.5 (4) | C68—C60—C59—C167 | 175.7 (3) |
Si1—O111—C30—C31 | −95.3 (3) | C65—C167—C59—O112 | 177.5 (3) |
Si1—O111—C30—C38 | 90.4 (3) | C78—C167—C59—O112 | 0.6 (4) |
C32—C31—C30—O111 | −176.2 (2) | C65—C167—C59—C60 | 2.3 (4) |
C39—C31—C30—O111 | 0.5 (4) | C78—C167—C59—C60 | −174.6 (3) |
C32—C31—C30—C38 | −1.9 (4) | C3—C5—C7—C9 | −0.3 (5) |
C39—C31—C30—C38 | 174.8 (2) | C1—C9—C7—C5 | 0.5 (4) |
C36—C38—C30—O111 | 175.5 (2) | C20—C9—C7—C5 | −177.1 (3) |
C49—C38—C30—O111 | −3.5 (4) | C60—C61—C63—C65 | 1.1 (6) |
C36—C38—C30—C31 | 1.3 (4) | C167—C65—C63—C61 | −0.8 (5) |
C49—C38—C30—C31 | −177.6 (3) | C95—N109—C102—C105 | 59.8 (4) |
C30—C31—C32—C34 | 1.1 (4) | C88—N109—C102—C105 | −173.2 (3) |
C39—C31—C32—C34 | −175.6 (3) | C36—C38—C49—C55 | 68.5 (3) |
C36—C34—C32—C31 | 0.3 (5) | C30—C38—C49—C55 | −112.6 (3) |
O110—C1—C9—C7 | 176.2 (2) | C36—C38—C49—C51 | −54.1 (4) |
C2—C1—C9—C7 | −0.2 (4) | C30—C38—C49—C51 | 124.8 (3) |
O110—C1—C9—C20 | −6.2 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N109—H115···S114 | 0.90 (3) | 2.20 (3) | 3.086 (3) | 169 (3) |
Crystal data top
C36H51O3SSi·C6H16N | F(000) = 1520 |
Mr = 694.11 | Dx = 1.099 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 2159 reflections |
a = 11.7471 (14) Å | θ = 3.1–29.0° |
b = 17.9659 (15) Å | µ = 0.14 mm−1 |
c = 20.250 (2) Å | T = 210 K |
β = 100.904 (9)° | Block, colourless |
V = 4196.6 (7) Å3 | 0.34 × 0.22 × 0.13 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 6652 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.070 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.2° |
rotation method scans | h = −14→14 |
20955 measured reflections | k = −19→22 |
8106 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 0.97 | Δρmax = 0.38 e Å−3 |
8106 reflections | Δρmin = −0.20 e Å−3 |
452 parameters | Absolute structure: Flack x determined using 2735 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
Si1 | 0.55640 (7) | 0.26217 (4) | 0.06094 (4) | 0.02175 (19) | |
S114 | 0.40929 (7) | 0.20963 (5) | 0.01672 (5) | 0.0320 (2) | |
O112 | 0.54748 (19) | 0.35395 (11) | 0.05777 (12) | 0.0273 (5) | |
O110 | 0.59177 (19) | 0.23995 (12) | 0.14198 (12) | 0.0265 (5) | |
O111 | 0.6731 (2) | 0.24827 (12) | 0.02840 (12) | 0.0275 (5) | |
N109 | 0.1980 (3) | 0.28290 (18) | −0.07379 (16) | 0.0355 (7) | |
H115 | 0.266 (3) | 0.2645 (19) | −0.0517 (19) | 0.021 (9)* | |
C38 | 0.7314 (3) | 0.14417 (19) | −0.03227 (18) | 0.0316 (8) | |
C78 | 0.5836 (3) | 0.3857 (2) | −0.07800 (19) | 0.0354 (8) | |
H79 | 0.5396 | 0.3443 | −0.0637 | 0.042* | |
C1 | 0.5328 (3) | 0.19694 (18) | 0.18166 (16) | 0.0257 (7) | |
C5 | 0.4258 (4) | 0.1120 (2) | 0.2667 (2) | 0.0412 (9) | |
H6 | 0.3901 | 0.0836 | 0.2954 | 0.049* | |
C31 | 0.8559 (3) | 0.1912 (2) | 0.07046 (19) | 0.0322 (8) | |
C2 | 0.4392 (3) | 0.2268 (2) | 0.20633 (17) | 0.0297 (7) | |
C39 | 0.8800 (3) | 0.2489 (2) | 0.1265 (2) | 0.0363 (9) | |
H40 | 0.8059 | 0.2618 | 0.139 | 0.044* | |
C45 | 0.9294 (4) | 0.3196 (2) | 0.1006 (2) | 0.0492 (10) | |
H46 | 1.0036 | 0.3089 | 0.0896 | 0.074* | |
H47 | 0.938 | 0.3572 | 0.1349 | 0.074* | |
H48 | 0.8775 | 0.337 | 0.0613 | 0.074* | |
C10 | 0.3954 (3) | 0.3055 (2) | 0.19118 (19) | 0.0353 (8) | |
H11 | 0.4334 | 0.3256 | 0.1559 | 0.042* | |
C41 | 0.9613 (4) | 0.2208 (3) | 0.1899 (2) | 0.0531 (11) | |
H42 | 0.9305 | 0.1758 | 0.2051 | 0.08* | |
H43 | 0.9679 | 0.2579 | 0.2245 | 0.08* | |
H44 | 1.0365 | 0.211 | 0.1797 | 0.08* | |
C22 | 0.6226 (5) | 0.0472 (3) | 0.1063 (3) | 0.0628 (13) | |
H23 | 0.584 | 0.0034 | 0.1181 | 0.094* | |
H24 | 0.6848 | 0.0329 | 0.0843 | 0.094* | |
H25 | 0.5683 | 0.0775 | 0.0765 | 0.094* | |
C34 | 0.9189 (4) | 0.0883 (2) | 0.0093 (2) | 0.0487 (10) | |
H35 | 0.9745 | 0.0526 | 0.005 | 0.058* | |
C20 | 0.6710 (3) | 0.0909 (2) | 0.1694 (2) | 0.0376 (8) | |
H21 | 0.7163 | 0.1322 | 0.1561 | 0.045* | |
C3 | 0.3870 (3) | 0.1822 (2) | 0.24940 (18) | 0.0372 (9) | |
H4 | 0.3246 | 0.201 | 0.2664 | 0.045* | |
C84 | 0.4974 (4) | 0.4388 (3) | −0.1194 (3) | 0.0562 (11) | |
H85 | 0.5379 | 0.4816 | −0.1315 | 0.084* | |
H86 | 0.4413 | 0.4542 | −0.0933 | 0.084* | |
H87 | 0.4588 | 0.414 | −0.1594 | 0.084* | |
C95 | 0.1074 (4) | 0.2486 (3) | −0.0398 (2) | 0.0454 (10) | |
H96 | 0.1133 | 0.1949 | −0.0424 | 0.054* | |
H97 | 0.1237 | 0.2624 | 0.0073 | 0.054* | |
C30 | 0.7518 (3) | 0.19289 (18) | 0.02300 (17) | 0.0272 (7) | |
C61 | 0.7604 (4) | 0.5043 (2) | 0.0962 (2) | 0.0478 (10) | |
H62 | 0.7976 | 0.5318 | 0.1329 | 0.057* | |
C32 | 0.9378 (3) | 0.1381 (2) | 0.0629 (2) | 0.0427 (9) | |
H33 | 1.0067 | 0.1357 | 0.0942 | 0.051* | |
C68 | 0.6571 (4) | 0.4354 (2) | 0.1759 (2) | 0.0400 (9) | |
H69 | 0.6048 | 0.3926 | 0.1736 | 0.048* | |
C70 | 0.7655 (5) | 0.4185 (3) | 0.2277 (2) | 0.0585 (12) | |
H71 | 0.8033 | 0.3755 | 0.2139 | 0.088* | |
H72 | 0.7444 | 0.4091 | 0.2705 | 0.088* | |
H73 | 0.8171 | 0.4604 | 0.2315 | 0.088* | |
C105 | 0.2260 (6) | 0.3972 (3) | −0.0040 (3) | 0.0676 (15) | |
H106 | 0.237 | 0.45 | −0.0062 | 0.101* | |
H107 | 0.2951 | 0.3747 | 0.0209 | 0.101* | |
H108 | 0.1621 | 0.387 | 0.0179 | 0.101* | |
C9 | 0.5736 (3) | 0.12466 (19) | 0.19869 (17) | 0.0296 (7) | |
C91 | 0.2945 (5) | 0.2623 (3) | −0.1728 (3) | 0.0638 (14) | |
H92 | 0.2856 | 0.2371 | −0.2153 | 0.096* | |
H93 | 0.3599 | 0.242 | −0.1425 | 0.096* | |
H94 | 0.3067 | 0.3144 | −0.1791 | 0.096* | |
C16 | 0.2646 (3) | 0.3082 (3) | 0.1654 (2) | 0.0509 (11) | |
H17 | 0.2434 | 0.2718 | 0.1306 | 0.076* | |
H18 | 0.243 | 0.3569 | 0.1477 | 0.076* | |
H19 | 0.225 | 0.2977 | 0.2017 | 0.076* | |
C60 | 0.6833 (3) | 0.44843 (19) | 0.1060 (2) | 0.0350 (8) | |
C36 | 0.8184 (4) | 0.0922 (2) | −0.0370 (2) | 0.0425 (9) | |
H37 | 0.8072 | 0.0592 | −0.073 | 0.051* | |
C88 | 0.1886 (4) | 0.2519 (3) | −0.1443 (2) | 0.0526 (11) | |
H89 | 0.1715 | 0.1991 | −0.1435 | 0.063* | |
H90 | 0.1241 | 0.2758 | −0.1736 | 0.063* | |
C12 | 0.4283 (4) | 0.3555 (2) | 0.2536 (2) | 0.0456 (10) | |
H13 | 0.3911 | 0.3374 | 0.2888 | 0.068* | |
H14 | 0.4034 | 0.4056 | 0.2423 | 0.068* | |
H15 | 0.5108 | 0.3547 | 0.2686 | 0.068* | |
C65 | 0.7270 (4) | 0.4802 (2) | −0.0216 (2) | 0.0456 (10) | |
H66 | 0.7423 | 0.4913 | −0.0639 | 0.055* | |
C80 | 0.6645 (4) | 0.3537 (3) | −0.1213 (3) | 0.0606 (13) | |
H81 | 0.6196 | 0.3288 | −0.1595 | 0.091* | |
H82 | 0.7165 | 0.3188 | −0.0954 | 0.091* | |
H83 | 0.7083 | 0.3932 | −0.1364 | 0.091* | |
C98 | −0.0145 (4) | 0.2713 (3) | −0.0696 (3) | 0.0629 (13) | |
H99 | −0.0289 | 0.2629 | −0.1172 | 0.094* | |
H100 | −0.0248 | 0.3232 | −0.0609 | 0.094* | |
H101 | −0.0679 | 0.2424 | −0.0496 | 0.094* | |
C167 | 0.6481 (3) | 0.4240 (2) | −0.01525 (18) | 0.0329 (8) | |
C59 | 0.6288 (3) | 0.40799 (17) | 0.04961 (19) | 0.0275 (7) | |
C26 | 0.7535 (4) | 0.0430 (3) | 0.2183 (3) | 0.0655 (14) | |
H27 | 0.7147 | −0.0018 | 0.2275 | 0.098* | |
H28 | 0.7785 | 0.07 | 0.2594 | 0.098* | |
H29 | 0.8196 | 0.0305 | 0.199 | 0.098* | |
C7 | 0.5184 (4) | 0.0830 (2) | 0.24166 (19) | 0.0384 (9) | |
H8 | 0.5441 | 0.0351 | 0.2536 | 0.046* | |
C74 | 0.5956 (5) | 0.5028 (3) | 0.1975 (3) | 0.0628 (13) | |
H75 | 0.5794 | 0.4945 | 0.2416 | 0.094* | |
H76 | 0.5243 | 0.5107 | 0.1663 | 0.094* | |
H77 | 0.6443 | 0.5458 | 0.1982 | 0.094* | |
C63 | 0.7830 (4) | 0.5199 (2) | 0.0333 (2) | 0.0534 (11) | |
H64 | 0.8358 | 0.5569 | 0.0279 | 0.064* | |
C102 | 0.2008 (4) | 0.3656 (2) | −0.0741 (2) | 0.0497 (10) | |
H103 | 0.1267 | 0.3843 | −0.0976 | 0.06* | |
H104 | 0.2599 | 0.3822 | −0.0984 | 0.06* | |
C49 | 0.6223 (3) | 0.1461 (2) | −0.08646 (19) | 0.0380 (9) | |
H50 | 0.5764 | 0.1894 | −0.0781 | 0.046* | |
C55 | 0.5474 (4) | 0.0768 (3) | −0.0860 (2) | 0.0530 (11) | |
H56 | 0.59 | 0.0338 | −0.0955 | 0.08* | |
H57 | 0.4783 | 0.0817 | −0.1197 | 0.08* | |
H58 | 0.5268 | 0.0714 | −0.0426 | 0.08* | |
C51 | 0.6526 (5) | 0.1549 (3) | −0.1566 (2) | 0.0569 (12) | |
H52 | 0.7008 | 0.198 | −0.1571 | 0.085* | |
H53 | 0.5826 | 0.1609 | −0.1894 | 0.085* | |
H54 | 0.6931 | 0.1115 | −0.1672 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0202 (4) | 0.0228 (4) | 0.0227 (5) | −0.0003 (4) | 0.0052 (4) | 0.0005 (4) |
S114 | 0.0251 (4) | 0.0284 (4) | 0.0402 (5) | −0.0049 (4) | −0.0002 (4) | 0.0006 (4) |
O112 | 0.0240 (11) | 0.0277 (11) | 0.0312 (13) | −0.0026 (10) | 0.0073 (10) | −0.0021 (10) |
O110 | 0.0234 (11) | 0.0319 (12) | 0.0253 (12) | −0.0025 (9) | 0.0075 (10) | 0.0032 (9) |
O111 | 0.0266 (11) | 0.0304 (12) | 0.0279 (13) | 0.0018 (9) | 0.0109 (10) | −0.0003 (9) |
N109 | 0.0297 (16) | 0.0443 (19) | 0.0307 (18) | 0.0009 (14) | 0.0011 (14) | 0.0062 (13) |
C38 | 0.0341 (19) | 0.0315 (18) | 0.031 (2) | 0.0029 (15) | 0.0097 (16) | 0.0011 (14) |
C78 | 0.039 (2) | 0.038 (2) | 0.029 (2) | −0.0072 (16) | 0.0071 (17) | 0.0035 (15) |
C1 | 0.0242 (15) | 0.0326 (18) | 0.0194 (17) | −0.0044 (13) | 0.0016 (13) | 0.0010 (13) |
C5 | 0.050 (2) | 0.045 (2) | 0.032 (2) | −0.0129 (18) | 0.0169 (19) | 0.0013 (16) |
C31 | 0.0287 (17) | 0.0369 (19) | 0.033 (2) | −0.0001 (14) | 0.0101 (16) | 0.0023 (15) |
C2 | 0.0274 (17) | 0.038 (2) | 0.0230 (18) | −0.0030 (14) | 0.0031 (15) | −0.0011 (14) |
C39 | 0.0275 (18) | 0.046 (2) | 0.036 (2) | −0.0029 (15) | 0.0089 (16) | −0.0068 (16) |
C45 | 0.041 (2) | 0.048 (2) | 0.061 (3) | −0.0089 (19) | 0.015 (2) | −0.012 (2) |
C10 | 0.0313 (18) | 0.043 (2) | 0.034 (2) | 0.0079 (15) | 0.0130 (16) | 0.0057 (16) |
C41 | 0.043 (2) | 0.078 (3) | 0.035 (2) | −0.008 (2) | −0.001 (2) | −0.006 (2) |
C22 | 0.070 (3) | 0.068 (3) | 0.053 (3) | 0.018 (3) | 0.018 (3) | −0.014 (2) |
C34 | 0.047 (2) | 0.045 (2) | 0.054 (3) | 0.017 (2) | 0.009 (2) | −0.003 (2) |
C20 | 0.038 (2) | 0.0292 (18) | 0.047 (2) | 0.0044 (15) | 0.0128 (18) | 0.0046 (16) |
C3 | 0.0356 (19) | 0.049 (2) | 0.030 (2) | −0.0066 (16) | 0.0142 (17) | −0.0006 (16) |
C84 | 0.052 (3) | 0.057 (3) | 0.056 (3) | 0.004 (2) | 0.000 (2) | 0.001 (2) |
C95 | 0.039 (2) | 0.059 (3) | 0.039 (2) | −0.0049 (18) | 0.0086 (19) | 0.0117 (19) |
C30 | 0.0262 (16) | 0.0285 (17) | 0.0293 (19) | 0.0031 (13) | 0.0115 (15) | 0.0013 (13) |
C61 | 0.053 (2) | 0.040 (2) | 0.048 (3) | −0.0205 (19) | 0.002 (2) | −0.0080 (18) |
C32 | 0.0312 (19) | 0.051 (2) | 0.044 (3) | 0.0093 (17) | 0.0014 (18) | 0.0047 (18) |
C68 | 0.051 (2) | 0.035 (2) | 0.033 (2) | −0.0109 (17) | 0.0071 (19) | −0.0073 (16) |
C70 | 0.073 (3) | 0.059 (3) | 0.041 (3) | 0.001 (2) | 0.005 (2) | 0.006 (2) |
C105 | 0.105 (4) | 0.048 (3) | 0.050 (3) | 0.018 (3) | 0.017 (3) | −0.004 (2) |
C9 | 0.0318 (18) | 0.0304 (17) | 0.0253 (19) | −0.0025 (14) | 0.0021 (15) | −0.0009 (14) |
C91 | 0.074 (3) | 0.073 (3) | 0.051 (3) | −0.005 (3) | 0.028 (3) | −0.015 (2) |
C16 | 0.034 (2) | 0.072 (3) | 0.046 (3) | 0.010 (2) | 0.006 (2) | 0.006 (2) |
C60 | 0.0373 (19) | 0.0312 (18) | 0.035 (2) | −0.0059 (15) | 0.0037 (16) | −0.0019 (15) |
C36 | 0.046 (2) | 0.034 (2) | 0.048 (2) | 0.0086 (17) | 0.012 (2) | −0.0086 (17) |
C88 | 0.053 (3) | 0.066 (3) | 0.037 (2) | −0.006 (2) | 0.003 (2) | −0.006 (2) |
C12 | 0.049 (2) | 0.042 (2) | 0.046 (2) | 0.0113 (19) | 0.009 (2) | −0.0011 (18) |
C65 | 0.052 (2) | 0.043 (2) | 0.044 (3) | −0.0145 (19) | 0.013 (2) | 0.0076 (18) |
C80 | 0.061 (3) | 0.073 (3) | 0.051 (3) | 0.002 (2) | 0.017 (3) | −0.018 (2) |
C98 | 0.040 (2) | 0.107 (4) | 0.042 (3) | −0.005 (3) | 0.007 (2) | 0.016 (3) |
C167 | 0.0348 (19) | 0.0297 (18) | 0.035 (2) | −0.0026 (14) | 0.0083 (17) | 0.0027 (14) |
C59 | 0.0247 (16) | 0.0221 (16) | 0.036 (2) | −0.0016 (13) | 0.0073 (15) | 0.0032 (14) |
C26 | 0.056 (3) | 0.072 (3) | 0.066 (3) | 0.024 (2) | 0.003 (3) | 0.004 (3) |
C7 | 0.049 (2) | 0.0294 (19) | 0.036 (2) | −0.0046 (16) | 0.0073 (18) | 0.0054 (15) |
C74 | 0.080 (4) | 0.062 (3) | 0.050 (3) | 0.017 (3) | 0.022 (3) | 0.002 (2) |
C63 | 0.060 (3) | 0.043 (2) | 0.059 (3) | −0.027 (2) | 0.015 (2) | 0.003 (2) |
C102 | 0.060 (3) | 0.046 (2) | 0.044 (3) | 0.005 (2) | 0.013 (2) | 0.0041 (19) |
C49 | 0.041 (2) | 0.043 (2) | 0.030 (2) | 0.0085 (17) | 0.0073 (17) | −0.0047 (16) |
C55 | 0.054 (3) | 0.055 (3) | 0.046 (3) | −0.007 (2) | 0.000 (2) | −0.009 (2) |
C51 | 0.071 (3) | 0.068 (3) | 0.033 (2) | 0.016 (2) | 0.013 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
Si1—O111 | 1.648 (2) | C61—C60 | 1.392 (5) |
Si1—O112 | 1.653 (2) | C61—H62 | 0.93 |
Si1—O110 | 1.664 (2) | C32—H33 | 0.93 |
Si1—S114 | 2.0233 (12) | C68—C74 | 1.515 (6) |
O112—C59 | 1.394 (4) | C68—C70 | 1.520 (6) |
O110—C1 | 1.391 (4) | C68—C60 | 1.523 (5) |
O111—C30 | 1.377 (4) | C68—H69 | 0.98 |
N109—C102 | 1.486 (5) | C70—H71 | 0.96 |
N109—C95 | 1.503 (5) | C70—H72 | 0.96 |
N109—C88 | 1.518 (5) | C70—H73 | 0.96 |
N109—H115 | 0.90 (4) | C105—C102 | 1.505 (7) |
C38—C36 | 1.401 (5) | C105—H106 | 0.96 |
C38—C30 | 1.405 (5) | C105—H107 | 0.96 |
C38—C49 | 1.521 (6) | C105—H108 | 0.96 |
C78—C167 | 1.516 (5) | C9—C7 | 1.397 (5) |
C78—C84 | 1.522 (6) | C91—C88 | 1.479 (7) |
C78—C80 | 1.523 (6) | C91—H92 | 0.96 |
C78—H79 | 0.98 | C91—H93 | 0.96 |
C1—C2 | 1.397 (5) | C91—H94 | 0.96 |
C1—C9 | 1.404 (5) | C16—H17 | 0.96 |
C5—C3 | 1.364 (6) | C16—H18 | 0.96 |
C5—C7 | 1.385 (6) | C16—H19 | 0.96 |
C5—H6 | 0.93 | C60—C59 | 1.402 (5) |
C31—C32 | 1.383 (5) | C36—H37 | 0.93 |
C31—C30 | 1.405 (5) | C88—H89 | 0.97 |
C31—C39 | 1.523 (5) | C88—H90 | 0.97 |
C2—C3 | 1.408 (5) | C12—H13 | 0.96 |
C2—C10 | 1.517 (5) | C12—H14 | 0.96 |
C39—C45 | 1.529 (6) | C12—H15 | 0.96 |
C39—C41 | 1.533 (6) | C65—C63 | 1.378 (6) |
C39—H40 | 0.98 | C65—C167 | 1.394 (5) |
C45—H46 | 0.96 | C65—H66 | 0.93 |
C45—H47 | 0.96 | C80—H81 | 0.96 |
C45—H48 | 0.96 | C80—H82 | 0.96 |
C10—C16 | 1.528 (5) | C80—H83 | 0.96 |
C10—C12 | 1.539 (6) | C98—H99 | 0.96 |
C10—H11 | 0.98 | C98—H100 | 0.96 |
C41—H42 | 0.96 | C98—H101 | 0.96 |
C41—H43 | 0.96 | C167—C59 | 1.404 (5) |
C41—H44 | 0.96 | C26—H27 | 0.96 |
C22—C20 | 1.518 (6) | C26—H28 | 0.96 |
C22—H23 | 0.96 | C26—H29 | 0.96 |
C22—H24 | 0.96 | C7—H8 | 0.93 |
C22—H25 | 0.96 | C74—H75 | 0.96 |
C34—C36 | 1.363 (6) | C74—H76 | 0.96 |
C34—C32 | 1.393 (6) | C74—H77 | 0.96 |
C34—H35 | 0.93 | C63—H64 | 0.93 |
C20—C9 | 1.511 (5) | C102—H103 | 0.97 |
C20—C26 | 1.515 (6) | C102—H104 | 0.97 |
C20—H21 | 0.98 | C49—C55 | 1.525 (6) |
C3—H4 | 0.93 | C49—C51 | 1.537 (6) |
C84—H85 | 0.96 | C49—H50 | 0.98 |
C84—H86 | 0.96 | C55—H56 | 0.96 |
C84—H87 | 0.96 | C55—H57 | 0.96 |
C95—C98 | 1.502 (6) | C55—H58 | 0.96 |
C95—H96 | 0.97 | C51—H52 | 0.96 |
C95—H97 | 0.97 | C51—H53 | 0.96 |
C61—C63 | 1.378 (6) | C51—H54 | 0.96 |
| | | |
O111—Si1—O112 | 100.78 (12) | H71—C70—H72 | 109.5 |
O111—Si1—O110 | 106.66 (12) | C68—C70—H73 | 109.5 |
O112—Si1—O110 | 106.25 (12) | H71—C70—H73 | 109.5 |
O111—Si1—S114 | 117.23 (10) | H72—C70—H73 | 109.5 |
O112—Si1—S114 | 113.94 (10) | C102—C105—H106 | 109.5 |
O110—Si1—S114 | 110.96 (9) | C102—C105—H107 | 109.5 |
C59—O112—Si1 | 131.3 (2) | H106—C105—H107 | 109.5 |
C1—O110—Si1 | 130.1 (2) | C102—C105—H108 | 109.5 |
C30—O111—Si1 | 139.7 (2) | H106—C105—H108 | 109.5 |
C102—N109—C95 | 115.5 (3) | H107—C105—H108 | 109.5 |
C102—N109—C88 | 111.2 (3) | C7—C9—C1 | 118.1 (3) |
C95—N109—C88 | 110.4 (3) | C7—C9—C20 | 120.3 (3) |
C102—N109—H115 | 110 (2) | C1—C9—C20 | 121.5 (3) |
C95—N109—H115 | 105 (2) | C88—C91—H92 | 109.5 |
C88—N109—H115 | 103 (2) | C88—C91—H93 | 109.5 |
C36—C38—C30 | 116.9 (3) | H92—C91—H93 | 109.5 |
C36—C38—C49 | 119.5 (3) | C88—C91—H94 | 109.5 |
C30—C38—C49 | 123.6 (3) | H92—C91—H94 | 109.5 |
C167—C78—C84 | 110.6 (3) | H93—C91—H94 | 109.5 |
C167—C78—C80 | 112.8 (3) | C10—C16—H17 | 109.5 |
C84—C78—C80 | 110.0 (4) | C10—C16—H18 | 109.5 |
C167—C78—H79 | 107.7 | H17—C16—H18 | 109.5 |
C84—C78—H79 | 107.7 | C10—C16—H19 | 109.5 |
C80—C78—H79 | 107.7 | H17—C16—H19 | 109.5 |
O110—C1—C2 | 120.3 (3) | H18—C16—H19 | 109.5 |
O110—C1—C9 | 118.1 (3) | C61—C60—C59 | 117.8 (4) |
C2—C1—C9 | 121.5 (3) | C61—C60—C68 | 119.7 (3) |
C3—C5—C7 | 120.0 (3) | C59—C60—C68 | 122.4 (3) |
C3—C5—H6 | 120 | C34—C36—C38 | 122.4 (4) |
C7—C5—H6 | 120 | C34—C36—H37 | 118.8 |
C32—C31—C30 | 118.2 (3) | C38—C36—H37 | 118.8 |
C32—C31—C39 | 121.0 (3) | C91—C88—N109 | 113.8 (4) |
C30—C31—C39 | 120.7 (3) | C91—C88—H89 | 108.8 |
C1—C2—C3 | 117.9 (3) | N109—C88—H89 | 108.8 |
C1—C2—C10 | 123.1 (3) | C91—C88—H90 | 108.8 |
C3—C2—C10 | 119.0 (3) | N109—C88—H90 | 108.8 |
C31—C39—C45 | 109.9 (3) | H89—C88—H90 | 107.7 |
C31—C39—C41 | 113.5 (3) | C10—C12—H13 | 109.5 |
C45—C39—C41 | 110.1 (3) | C10—C12—H14 | 109.5 |
C31—C39—H40 | 107.7 | H13—C12—H14 | 109.5 |
C45—C39—H40 | 107.7 | C10—C12—H15 | 109.5 |
C41—C39—H40 | 107.7 | H13—C12—H15 | 109.5 |
C39—C45—H46 | 109.5 | H14—C12—H15 | 109.5 |
C39—C45—H47 | 109.5 | C63—C65—C167 | 121.6 (4) |
H46—C45—H47 | 109.5 | C63—C65—H66 | 119.2 |
C39—C45—H48 | 109.5 | C167—C65—H66 | 119.2 |
H46—C45—H48 | 109.5 | C78—C80—H81 | 109.5 |
H47—C45—H48 | 109.5 | C78—C80—H82 | 109.5 |
C2—C10—C16 | 112.3 (3) | H81—C80—H82 | 109.5 |
C2—C10—C12 | 110.8 (3) | C78—C80—H83 | 109.5 |
C16—C10—C12 | 110.0 (3) | H81—C80—H83 | 109.5 |
C2—C10—H11 | 107.9 | H82—C80—H83 | 109.5 |
C16—C10—H11 | 107.9 | C95—C98—H99 | 109.5 |
C12—C10—H11 | 107.9 | C95—C98—H100 | 109.5 |
C39—C41—H42 | 109.5 | H99—C98—H100 | 109.5 |
C39—C41—H43 | 109.5 | C95—C98—H101 | 109.5 |
H42—C41—H43 | 109.5 | H99—C98—H101 | 109.5 |
C39—C41—H44 | 109.5 | H100—C98—H101 | 109.5 |
H42—C41—H44 | 109.5 | C65—C167—C59 | 117.6 (3) |
H43—C41—H44 | 109.5 | C65—C167—C78 | 119.2 (3) |
C20—C22—H23 | 109.5 | C59—C167—C78 | 123.2 (3) |
C20—C22—H24 | 109.5 | O112—C59—C60 | 118.8 (3) |
H23—C22—H24 | 109.5 | O112—C59—C167 | 119.3 (3) |
C20—C22—H25 | 109.5 | C60—C59—C167 | 121.8 (3) |
H23—C22—H25 | 109.5 | C20—C26—H27 | 109.5 |
H24—C22—H25 | 109.5 | C20—C26—H28 | 109.5 |
C36—C34—C32 | 119.5 (4) | H27—C26—H28 | 109.5 |
C36—C34—H35 | 120.3 | C20—C26—H29 | 109.5 |
C32—C34—H35 | 120.3 | H27—C26—H29 | 109.5 |
C9—C20—C26 | 114.2 (3) | H28—C26—H29 | 109.5 |
C9—C20—C22 | 110.3 (3) | C5—C7—C9 | 121.1 (3) |
C26—C20—C22 | 110.3 (4) | C5—C7—H8 | 119.4 |
C9—C20—H21 | 107.2 | C9—C7—H8 | 119.4 |
C26—C20—H21 | 107.2 | C68—C74—H75 | 109.5 |
C22—C20—H21 | 107.2 | C68—C74—H76 | 109.5 |
C5—C3—C2 | 121.5 (3) | H75—C74—H76 | 109.5 |
C5—C3—H4 | 119.3 | C68—C74—H77 | 109.5 |
C2—C3—H4 | 119.3 | H75—C74—H77 | 109.5 |
C78—C84—H85 | 109.5 | H76—C74—H77 | 109.5 |
C78—C84—H86 | 109.5 | C65—C63—C61 | 119.7 (4) |
H85—C84—H86 | 109.5 | C65—C63—H64 | 120.2 |
C78—C84—H87 | 109.5 | C61—C63—H64 | 120.2 |
H85—C84—H87 | 109.5 | N109—C102—C105 | 111.9 (4) |
H86—C84—H87 | 109.5 | N109—C102—H103 | 109.2 |
C98—C95—N109 | 114.2 (3) | C105—C102—H103 | 109.2 |
C98—C95—H96 | 108.7 | N109—C102—H104 | 109.2 |
N109—C95—H96 | 108.7 | C105—C102—H104 | 109.2 |
C98—C95—H97 | 108.7 | H103—C102—H104 | 107.9 |
N109—C95—H97 | 108.7 | C38—C49—C55 | 112.6 (3) |
H96—C95—H97 | 107.6 | C38—C49—C51 | 111.0 (3) |
O111—C30—C38 | 119.8 (3) | C55—C49—C51 | 108.9 (4) |
O111—C30—C31 | 118.2 (3) | C38—C49—H50 | 108 |
C38—C30—C31 | 121.8 (3) | C55—C49—H50 | 108 |
C63—C61—C60 | 121.5 (4) | C51—C49—H50 | 108 |
C63—C61—H62 | 119.2 | C49—C55—H56 | 109.5 |
C60—C61—H62 | 119.2 | C49—C55—H57 | 109.5 |
C31—C32—C34 | 121.2 (4) | H56—C55—H57 | 109.5 |
C31—C32—H33 | 119.4 | C49—C55—H58 | 109.5 |
C34—C32—H33 | 119.4 | H56—C55—H58 | 109.5 |
C74—C68—C70 | 110.1 (4) | H57—C55—H58 | 109.5 |
C74—C68—C60 | 109.7 (3) | C49—C51—H52 | 109.5 |
C70—C68—C60 | 112.5 (4) | C49—C51—H53 | 109.5 |
C74—C68—H69 | 108.2 | H52—C51—H53 | 109.5 |
C70—C68—H69 | 108.2 | C49—C51—H54 | 109.5 |
C60—C68—H69 | 108.2 | H52—C51—H54 | 109.5 |
C68—C70—H71 | 109.5 | H53—C51—H54 | 109.5 |
C68—C70—H72 | 109.5 | | |
| | | |
O111—Si1—O112—C59 | −17.0 (3) | C2—C1—C9—C20 | 177.1 (3) |
O110—Si1—O112—C59 | 94.0 (3) | C26—C20—C9—C7 | −40.0 (5) |
S114—Si1—O112—C59 | −143.5 (3) | C22—C20—C9—C7 | 84.9 (4) |
O111—Si1—O110—C1 | −133.6 (3) | C26—C20—C9—C1 | 142.6 (4) |
O112—Si1—O110—C1 | 119.5 (3) | C22—C20—C9—C1 | −92.5 (4) |
S114—Si1—O110—C1 | −4.8 (3) | C63—C61—C60—C59 | 0.0 (6) |
O112—Si1—O111—C30 | 165.2 (3) | C63—C61—C60—C68 | −177.4 (4) |
O110—Si1—O111—C30 | 54.4 (4) | C74—C68—C60—C61 | 65.2 (5) |
S114—Si1—O111—C30 | −70.6 (4) | C70—C68—C60—C61 | −57.6 (5) |
Si1—O110—C1—C2 | −78.5 (4) | C74—C68—C60—C59 | −112.1 (4) |
Si1—O110—C1—C9 | 104.6 (3) | C70—C68—C60—C59 | 125.1 (4) |
O110—C1—C2—C3 | −176.4 (3) | C32—C34—C36—C38 | −1.0 (6) |
C9—C1—C2—C3 | 0.3 (5) | C30—C38—C36—C34 | −0.1 (6) |
O110—C1—C2—C10 | 0.9 (5) | C49—C38—C36—C34 | 179.0 (4) |
C9—C1—C2—C10 | 177.7 (3) | C102—N109—C88—C91 | 69.7 (5) |
C32—C31—C39—C45 | 93.1 (4) | C95—N109—C88—C91 | −160.8 (4) |
C30—C31—C39—C45 | −83.7 (4) | C63—C65—C167—C59 | −1.1 (6) |
C32—C31—C39—C41 | −30.7 (5) | C63—C65—C167—C78 | 176.2 (4) |
C30—C31—C39—C41 | 152.5 (3) | C84—C78—C167—C65 | −69.1 (5) |
C1—C2—C10—C16 | 129.3 (4) | C80—C78—C167—C65 | 54.6 (5) |
C3—C2—C10—C16 | −53.3 (5) | C84—C78—C167—C59 | 108.0 (4) |
C1—C2—C10—C12 | −107.2 (4) | C80—C78—C167—C59 | −128.3 (4) |
C3—C2—C10—C12 | 70.1 (4) | Si1—O112—C59—C60 | −103.3 (3) |
C7—C5—C3—C2 | −0.2 (6) | Si1—O112—C59—C167 | 81.0 (4) |
C1—C2—C3—C5 | 0.0 (5) | C61—C60—C59—O112 | −177.3 (3) |
C10—C2—C3—C5 | −177.5 (4) | C68—C60—C59—O112 | 0.1 (5) |
C102—N109—C95—C98 | 58.6 (5) | C61—C60—C59—C167 | −1.7 (5) |
C88—N109—C95—C98 | −68.5 (5) | C68—C60—C59—C167 | 175.7 (4) |
Si1—O111—C30—C38 | 90.4 (4) | C65—C167—C59—O112 | 177.8 (3) |
Si1—O111—C30—C31 | −95.2 (4) | C78—C167—C59—O112 | 0.6 (5) |
C36—C38—C30—O111 | 175.9 (3) | C65—C167—C59—C60 | 2.2 (5) |
C49—C38—C30—O111 | −3.1 (5) | C78—C167—C59—C60 | −175.0 (3) |
C36—C38—C30—C31 | 1.7 (5) | C3—C5—C7—C9 | 0.2 (6) |
C49—C38—C30—C31 | −177.3 (3) | C1—C9—C7—C5 | 0.1 (5) |
C32—C31—C30—O111 | −176.5 (3) | C20—C9—C7—C5 | −177.3 (4) |
C39—C31—C30—O111 | 0.4 (5) | C167—C65—C63—C61 | −0.5 (7) |
C32—C31—C30—C38 | −2.1 (5) | C60—C61—C63—C65 | 1.0 (7) |
C39—C31—C30—C38 | 174.8 (3) | C95—N109—C102—C105 | 60.9 (5) |
C30—C31—C32—C34 | 1.0 (6) | C88—N109—C102—C105 | −172.4 (4) |
C39—C31—C32—C34 | −175.9 (4) | C36—C38—C49—C55 | 67.8 (4) |
C36—C34—C32—C31 | 0.6 (6) | C30—C38—C49—C55 | −113.2 (4) |
O110—C1—C9—C7 | 176.4 (3) | C36—C38—C49—C51 | −54.6 (5) |
C2—C1—C9—C7 | −0.4 (5) | C30—C38—C49—C51 | 124.4 (4) |
O110—C1—C9—C20 | −6.1 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N109—H115···S114 | 0.90 (4) | 2.20 (4) | 3.087 (3) | 168 (3) |
Crystal data top
C36H51O3SSi·C6H16N | F(000) = 1520 |
Mr = 694.11 | Dx = 1.093 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 807 reflections |
a = 11.801 (2) Å | θ = 3.1–27.8° |
b = 18.019 (2) Å | µ = 0.14 mm−1 |
c = 20.201 (4) Å | T = 240 K |
β = 100.958 (15)° | Block, colourless |
V = 4217.1 (13) Å3 | 0.34 × 0.22 × 0.13 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 4927 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.045 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.2° |
rotation method scans | h = −12→14 |
7448 measured reflections | k = −17→22 |
5960 independent reflections | l = −24→23 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.04 | Δρmax = 0.36 e Å−3 |
5960 reflections | Δρmin = −0.45 e Å−3 |
452 parameters | Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. |
2 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
Si1 | 0.55619 (9) | 0.26273 (7) | 0.06093 (7) | 0.0267 (3) | |
S114 | 0.41002 (11) | 0.21026 (7) | 0.01677 (8) | 0.0381 (3) | |
O112 | 0.5485 (3) | 0.35391 (18) | 0.05773 (19) | 0.0311 (7) | |
O110 | 0.5916 (3) | 0.2407 (2) | 0.14212 (18) | 0.0325 (8) | |
O111 | 0.6726 (3) | 0.2482 (2) | 0.02845 (19) | 0.0332 (8) | |
N109 | 0.1968 (4) | 0.2829 (3) | −0.0733 (3) | 0.0436 (12) | |
H115 | 0.255 (5) | 0.266 (3) | −0.052 (3) | 0.019 (13)* | |
C38 | 0.7315 (5) | 0.1438 (3) | −0.0315 (3) | 0.0376 (12) | |
C78 | 0.5832 (5) | 0.3858 (3) | −0.0782 (3) | 0.0421 (13) | |
H79 | 0.5392 | 0.3447 | −0.0638 | 0.05* | |
C1 | 0.5330 (4) | 0.1973 (3) | 0.1813 (3) | 0.0306 (10) | |
C5 | 0.4270 (6) | 0.1127 (4) | 0.2666 (3) | 0.0501 (15) | |
H6 | 0.3924 | 0.0845 | 0.2958 | 0.06* | |
C31 | 0.8557 (5) | 0.1921 (3) | 0.0707 (3) | 0.0383 (12) | |
C2 | 0.4395 (5) | 0.2276 (3) | 0.2064 (3) | 0.0341 (11) | |
C39 | 0.8792 (5) | 0.2503 (4) | 0.1259 (3) | 0.0434 (13) | |
H40 | 0.8053 | 0.2632 | 0.1383 | 0.052* | |
C45 | 0.9285 (6) | 0.3211 (4) | 0.0999 (4) | 0.0598 (18) | |
H46 | 0.9983 | 0.3093 | 0.0843 | 0.09* | |
H47 | 0.9447 | 0.3568 | 0.1357 | 0.09* | |
H48 | 0.8731 | 0.3414 | 0.0634 | 0.09* | |
C10 | 0.3956 (5) | 0.3054 (3) | 0.1910 (3) | 0.0400 (12) | |
H11 | 0.4334 | 0.3254 | 0.1556 | 0.048* | |
C41 | 0.9601 (7) | 0.2226 (5) | 0.1896 (4) | 0.067 (2) | |
H42 | 0.9313 | 0.1766 | 0.2039 | 0.101* | |
H43 | 0.9638 | 0.2588 | 0.2248 | 0.101* | |
H44 | 1.0359 | 0.2149 | 0.1801 | 0.101* | |
C22 | 0.6227 (8) | 0.0464 (6) | 0.1071 (4) | 0.078 (2) | |
H23 | 0.5919 | 0.0006 | 0.1204 | 0.117* | |
H24 | 0.6837 | 0.0358 | 0.0831 | 0.117* | |
H25 | 0.5628 | 0.0736 | 0.0784 | 0.117* | |
C34 | 0.9180 (6) | 0.0893 (4) | 0.0100 (4) | 0.0608 (18) | |
H35 | 0.9733 | 0.0536 | 0.006 | 0.073* | |
C20 | 0.6695 (5) | 0.0917 (3) | 0.1686 (3) | 0.0460 (13) | |
H21 | 0.7133 | 0.1328 | 0.1541 | 0.055* | |
C3 | 0.3877 (5) | 0.1825 (4) | 0.2492 (3) | 0.0453 (14) | |
H4 | 0.3251 | 0.2008 | 0.266 | 0.054* | |
C84 | 0.4976 (7) | 0.4390 (5) | −0.1187 (4) | 0.067 (2) | |
H85 | 0.5375 | 0.4824 | −0.1295 | 0.101* | |
H86 | 0.4409 | 0.453 | −0.0927 | 0.101* | |
H87 | 0.4602 | 0.4152 | −0.1596 | 0.101* | |
C95 | 0.1076 (6) | 0.2481 (5) | −0.0403 (4) | 0.0555 (17) | |
H96 | 0.1228 | 0.2618 | 0.007 | 0.067* | |
H97 | 0.1148 | 0.1946 | −0.0427 | 0.067* | |
C30 | 0.7511 (4) | 0.1939 (3) | 0.0230 (3) | 0.0345 (11) | |
C61 | 0.7582 (7) | 0.5051 (4) | 0.0959 (4) | 0.0595 (18) | |
H62 | 0.7947 | 0.5325 | 0.1329 | 0.071* | |
C32 | 0.9362 (6) | 0.1399 (4) | 0.0632 (4) | 0.0546 (16) | |
H33 | 1.005 | 0.138 | 0.0945 | 0.065* | |
C68 | 0.6572 (6) | 0.4363 (4) | 0.1756 (3) | 0.0494 (15) | |
H69 | 0.6055 | 0.3934 | 0.1733 | 0.059* | |
C70 | 0.7646 (8) | 0.4195 (5) | 0.2268 (4) | 0.073 (2) | |
H71 | 0.7978 | 0.3738 | 0.2152 | 0.109* | |
H72 | 0.7452 | 0.415 | 0.2707 | 0.109* | |
H73 | 0.8194 | 0.459 | 0.2272 | 0.109* | |
C105 | 0.2292 (10) | 0.3970 (5) | −0.0040 (5) | 0.085 (3) | |
H106 | 0.2324 | 0.4501 | −0.0067 | 0.128* | |
H107 | 0.3025 | 0.3784 | 0.0188 | 0.128* | |
H108 | 0.1704 | 0.3829 | 0.0205 | 0.128* | |
C9 | 0.5735 (5) | 0.1252 (3) | 0.1981 (3) | 0.0355 (11) | |
C91 | 0.2944 (8) | 0.2614 (6) | −0.1717 (5) | 0.076 (2) | |
H92 | 0.2844 | 0.2382 | −0.2152 | 0.113* | |
H93 | 0.359 | 0.2393 | −0.1421 | 0.113* | |
H94 | 0.3084 | 0.3135 | −0.1762 | 0.113* | |
C16 | 0.2662 (6) | 0.3072 (5) | 0.1649 (4) | 0.0607 (19) | |
H17 | 0.2457 | 0.2698 | 0.1309 | 0.091* | |
H18 | 0.2444 | 0.3551 | 0.1458 | 0.091* | |
H19 | 0.2267 | 0.2979 | 0.2014 | 0.091* | |
C60 | 0.6823 (5) | 0.4492 (3) | 0.1055 (3) | 0.0436 (13) | |
C36 | 0.8176 (6) | 0.0932 (4) | −0.0360 (4) | 0.0520 (15) | |
H37 | 0.8064 | 0.0603 | −0.0721 | 0.062* | |
C88 | 0.1893 (7) | 0.2510 (6) | −0.1434 (4) | 0.069 (2) | |
H89 | 0.1731 | 0.1983 | −0.142 | 0.083* | |
H90 | 0.1249 | 0.274 | −0.1734 | 0.083* | |
C12 | 0.4284 (6) | 0.3555 (4) | 0.2537 (4) | 0.0551 (16) | |
H13 | 0.3896 | 0.3383 | 0.2885 | 0.083* | |
H14 | 0.4057 | 0.4057 | 0.242 | 0.083* | |
H15 | 0.5104 | 0.3535 | 0.2696 | 0.083* | |
C65 | 0.7243 (6) | 0.4807 (4) | −0.0220 (4) | 0.0576 (17) | |
H66 | 0.7385 | 0.4919 | −0.0646 | 0.069* | |
C80 | 0.6636 (7) | 0.3535 (6) | −0.1210 (4) | 0.073 (2) | |
H81 | 0.6197 | 0.3251 | −0.1572 | 0.11* | |
H82 | 0.7193 | 0.322 | −0.0937 | 0.11* | |
H83 | 0.7028 | 0.3931 | −0.1393 | 0.11* | |
C98 | −0.0147 (7) | 0.2696 (6) | −0.0708 (5) | 0.078 (3) | |
H99 | −0.0259 | 0.2659 | −0.119 | 0.117* | |
H100 | −0.0288 | 0.3196 | −0.0583 | 0.117* | |
H101 | −0.0674 | 0.2367 | −0.0545 | 0.117* | |
C167 | 0.6474 (5) | 0.4240 (3) | −0.0153 (3) | 0.0404 (12) | |
C59 | 0.6278 (5) | 0.4078 (3) | 0.0490 (3) | 0.0353 (11) | |
C26 | 0.7544 (7) | 0.0450 (6) | 0.2183 (5) | 0.078 (2) | |
H27 | 0.7167 | 0.0007 | 0.2292 | 0.117* | |
H28 | 0.7808 | 0.0732 | 0.2586 | 0.117* | |
H29 | 0.8192 | 0.0319 | 0.1982 | 0.117* | |
C7 | 0.5185 (6) | 0.0836 (3) | 0.2408 (3) | 0.0446 (13) | |
H8 | 0.5435 | 0.0355 | 0.2522 | 0.054* | |
C74 | 0.5953 (8) | 0.5026 (6) | 0.1972 (4) | 0.077 (2) | |
H75 | 0.5851 | 0.4957 | 0.2429 | 0.115* | |
H76 | 0.5213 | 0.5077 | 0.1682 | 0.115* | |
H77 | 0.6403 | 0.5465 | 0.1945 | 0.115* | |
C63 | 0.7808 (7) | 0.5212 (5) | 0.0336 (4) | 0.070 (2) | |
H64 | 0.8329 | 0.5584 | 0.0283 | 0.083* | |
C102 | 0.2014 (7) | 0.3650 (4) | −0.0739 (4) | 0.0621 (18) | |
H103 | 0.1275 | 0.3842 | −0.0968 | 0.075* | |
H104 | 0.2595 | 0.3808 | −0.099 | 0.075* | |
C49 | 0.6228 (5) | 0.1459 (4) | −0.0859 (3) | 0.0446 (13) | |
H50 | 0.5771 | 0.1891 | −0.0773 | 0.054* | |
C55 | 0.5491 (7) | 0.0773 (5) | −0.0850 (4) | 0.066 (2) | |
H56 | 0.5923 | 0.0343 | −0.0932 | 0.099* | |
H57 | 0.4811 | 0.0813 | −0.1195 | 0.099* | |
H58 | 0.5271 | 0.0729 | −0.0418 | 0.099* | |
C51 | 0.6538 (8) | 0.1554 (5) | −0.1559 (4) | 0.069 (2) | |
H52 | 0.7079 | 0.1953 | −0.1547 | 0.104* | |
H53 | 0.5852 | 0.1664 | −0.1883 | 0.104* | |
H54 | 0.6875 | 0.1103 | −0.1685 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0205 (6) | 0.0342 (6) | 0.0260 (7) | −0.0011 (5) | 0.0060 (5) | −0.0003 (6) |
S114 | 0.0277 (6) | 0.0421 (6) | 0.0418 (7) | −0.0069 (5) | −0.0004 (5) | −0.0001 (6) |
O112 | 0.0255 (16) | 0.0320 (16) | 0.0373 (18) | −0.0057 (14) | 0.0099 (13) | −0.0006 (16) |
O110 | 0.0236 (16) | 0.047 (2) | 0.0277 (18) | −0.0050 (14) | 0.0067 (13) | 0.0013 (15) |
O111 | 0.0264 (17) | 0.044 (2) | 0.0308 (19) | −0.0002 (14) | 0.0104 (14) | −0.0009 (15) |
N109 | 0.029 (2) | 0.059 (3) | 0.039 (3) | 0.002 (2) | −0.001 (2) | 0.010 (2) |
C38 | 0.033 (3) | 0.044 (3) | 0.037 (3) | 0.002 (2) | 0.009 (2) | 0.000 (2) |
C78 | 0.044 (3) | 0.049 (3) | 0.033 (3) | −0.007 (2) | 0.009 (2) | 0.003 (2) |
C1 | 0.024 (2) | 0.041 (3) | 0.026 (2) | −0.0017 (18) | 0.0034 (19) | 0.004 (2) |
C5 | 0.060 (4) | 0.060 (4) | 0.035 (3) | −0.015 (3) | 0.020 (3) | 0.001 (3) |
C31 | 0.029 (3) | 0.051 (3) | 0.034 (3) | −0.002 (2) | 0.005 (2) | 0.001 (2) |
C2 | 0.031 (3) | 0.043 (3) | 0.030 (3) | −0.006 (2) | 0.008 (2) | 0.000 (2) |
C39 | 0.028 (3) | 0.065 (4) | 0.038 (3) | −0.004 (2) | 0.007 (2) | −0.010 (3) |
C45 | 0.045 (3) | 0.066 (4) | 0.069 (5) | −0.008 (3) | 0.013 (3) | −0.013 (4) |
C10 | 0.035 (3) | 0.051 (3) | 0.037 (3) | 0.013 (2) | 0.013 (2) | 0.009 (2) |
C41 | 0.053 (4) | 0.104 (6) | 0.041 (4) | −0.011 (4) | 0.000 (3) | −0.011 (4) |
C22 | 0.080 (6) | 0.096 (6) | 0.057 (5) | 0.027 (5) | 0.013 (4) | −0.020 (4) |
C34 | 0.049 (4) | 0.060 (4) | 0.073 (5) | 0.026 (3) | 0.011 (3) | −0.007 (4) |
C20 | 0.045 (3) | 0.045 (3) | 0.051 (4) | 0.008 (2) | 0.016 (3) | 0.005 (3) |
C3 | 0.046 (3) | 0.061 (4) | 0.033 (3) | −0.006 (3) | 0.018 (3) | 0.001 (3) |
C84 | 0.054 (4) | 0.083 (5) | 0.058 (4) | 0.002 (4) | −0.010 (3) | 0.002 (4) |
C95 | 0.044 (4) | 0.077 (5) | 0.046 (4) | −0.001 (3) | 0.007 (3) | 0.020 (3) |
C30 | 0.027 (2) | 0.044 (3) | 0.034 (3) | 0.004 (2) | 0.010 (2) | 0.003 (2) |
C61 | 0.067 (4) | 0.055 (4) | 0.056 (4) | −0.026 (3) | 0.008 (3) | −0.006 (3) |
C32 | 0.039 (3) | 0.063 (4) | 0.059 (4) | 0.012 (3) | 0.004 (3) | 0.009 (3) |
C68 | 0.060 (4) | 0.051 (3) | 0.037 (3) | −0.013 (3) | 0.008 (3) | −0.008 (3) |
C70 | 0.086 (6) | 0.079 (5) | 0.051 (4) | 0.009 (4) | 0.007 (4) | 0.009 (4) |
C105 | 0.130 (8) | 0.069 (5) | 0.057 (5) | 0.024 (5) | 0.015 (5) | −0.005 (4) |
C9 | 0.038 (3) | 0.039 (3) | 0.029 (3) | 0.001 (2) | 0.005 (2) | 0.001 (2) |
C91 | 0.080 (6) | 0.094 (7) | 0.055 (5) | −0.003 (4) | 0.019 (4) | −0.015 (4) |
C16 | 0.039 (3) | 0.086 (5) | 0.055 (4) | 0.017 (3) | 0.005 (3) | 0.006 (4) |
C60 | 0.043 (3) | 0.047 (3) | 0.041 (3) | −0.005 (2) | 0.008 (2) | −0.003 (3) |
C36 | 0.054 (4) | 0.054 (4) | 0.049 (4) | 0.012 (3) | 0.013 (3) | −0.012 (3) |
C88 | 0.064 (5) | 0.095 (6) | 0.048 (4) | −0.009 (4) | 0.008 (4) | −0.011 (4) |
C12 | 0.060 (4) | 0.055 (4) | 0.052 (4) | 0.013 (3) | 0.015 (3) | 0.003 (3) |
C65 | 0.064 (4) | 0.060 (4) | 0.052 (4) | −0.024 (3) | 0.019 (3) | 0.009 (3) |
C80 | 0.071 (5) | 0.097 (6) | 0.054 (4) | −0.003 (4) | 0.017 (4) | −0.022 (4) |
C98 | 0.044 (4) | 0.134 (8) | 0.054 (5) | −0.003 (4) | 0.007 (3) | 0.023 (5) |
C167 | 0.040 (3) | 0.048 (3) | 0.033 (3) | −0.006 (2) | 0.007 (2) | 0.004 (2) |
C59 | 0.030 (2) | 0.038 (3) | 0.039 (3) | 0.002 (2) | 0.007 (2) | 0.004 (2) |
C26 | 0.061 (5) | 0.094 (6) | 0.075 (6) | 0.029 (4) | 0.001 (4) | 0.002 (5) |
C7 | 0.055 (3) | 0.042 (3) | 0.039 (3) | −0.004 (2) | 0.013 (3) | 0.003 (2) |
C74 | 0.082 (6) | 0.092 (6) | 0.059 (5) | 0.018 (5) | 0.021 (4) | −0.006 (4) |
C63 | 0.069 (5) | 0.066 (4) | 0.073 (5) | −0.043 (4) | 0.012 (4) | 0.010 (4) |
C102 | 0.077 (5) | 0.053 (4) | 0.058 (4) | 0.002 (3) | 0.014 (4) | 0.003 (3) |
C49 | 0.043 (3) | 0.056 (4) | 0.034 (3) | 0.010 (3) | 0.005 (2) | −0.004 (3) |
C55 | 0.063 (5) | 0.076 (5) | 0.054 (4) | −0.015 (4) | 0.001 (3) | −0.013 (4) |
C51 | 0.088 (6) | 0.087 (6) | 0.033 (3) | 0.014 (4) | 0.011 (3) | 0.000 (3) |
Geometric parameters (Å, º) top
Si1—O112 | 1.646 (3) | C61—C60 | 1.386 (9) |
Si1—O111 | 1.652 (4) | C61—H62 | 0.93 |
Si1—O110 | 1.662 (4) | C32—H33 | 0.93 |
Si1—S114 | 2.0199 (18) | C68—C74 | 1.508 (11) |
O112—C59 | 1.382 (6) | C68—C70 | 1.508 (11) |
O110—C1 | 1.387 (6) | C68—C60 | 1.518 (9) |
O111—C30 | 1.367 (7) | C68—H69 | 0.98 |
N109—C102 | 1.481 (9) | C70—H71 | 0.96 |
N109—C95 | 1.487 (8) | C70—H72 | 0.96 |
N109—C88 | 1.516 (10) | C70—H73 | 0.96 |
N109—H115 | 0.80 (6) | C105—C102 | 1.502 (12) |
C38—C36 | 1.381 (9) | C105—H106 | 0.96 |
C38—C30 | 1.408 (8) | C105—H107 | 0.96 |
C38—C49 | 1.523 (8) | C105—H108 | 0.96 |
C78—C84 | 1.514 (10) | C9—C7 | 1.393 (8) |
C78—C167 | 1.515 (8) | C91—C88 | 1.473 (12) |
C78—C80 | 1.517 (10) | C91—H92 | 0.96 |
C78—H79 | 0.98 | C91—H93 | 0.96 |
C1—C9 | 1.403 (7) | C91—H94 | 0.96 |
C1—C2 | 1.408 (7) | C16—H17 | 0.96 |
C5—C3 | 1.364 (10) | C16—H18 | 0.96 |
C5—C7 | 1.388 (9) | C16—H19 | 0.96 |
C5—H6 | 0.93 | C60—C59 | 1.412 (8) |
C31—C32 | 1.365 (9) | C36—H37 | 0.93 |
C31—C30 | 1.415 (8) | C88—H89 | 0.97 |
C31—C39 | 1.518 (8) | C88—H90 | 0.97 |
C2—C3 | 1.407 (8) | C12—H13 | 0.96 |
C2—C10 | 1.507 (8) | C12—H14 | 0.96 |
C39—C41 | 1.534 (10) | C12—H15 | 0.96 |
C39—C45 | 1.535 (10) | C65—C167 | 1.389 (9) |
C39—H40 | 0.98 | C65—C63 | 1.399 (11) |
C45—H46 | 0.96 | C65—H66 | 0.93 |
C45—H47 | 0.96 | C80—H81 | 0.96 |
C45—H48 | 0.96 | C80—H82 | 0.96 |
C10—C16 | 1.518 (9) | C80—H83 | 0.96 |
C10—C12 | 1.544 (10) | C98—H99 | 0.96 |
C10—H11 | 0.98 | C98—H100 | 0.96 |
C41—H42 | 0.96 | C98—H101 | 0.96 |
C41—H43 | 0.96 | C167—C59 | 1.394 (8) |
C41—H44 | 0.96 | C26—H27 | 0.96 |
C22—C20 | 1.502 (11) | C26—H28 | 0.96 |
C22—H23 | 0.96 | C26—H29 | 0.96 |
C22—H24 | 0.96 | C7—H8 | 0.93 |
C22—H25 | 0.96 | C74—H75 | 0.96 |
C34—C36 | 1.361 (10) | C74—H76 | 0.96 |
C34—C32 | 1.396 (11) | C74—H77 | 0.96 |
C34—H35 | 0.93 | C63—H64 | 0.93 |
C20—C9 | 1.504 (8) | C102—H103 | 0.97 |
C20—C26 | 1.528 (10) | C102—H104 | 0.97 |
C20—H21 | 0.98 | C49—C55 | 1.513 (10) |
C3—H4 | 0.93 | C49—C51 | 1.536 (10) |
C84—H85 | 0.96 | C49—H50 | 0.98 |
C84—H86 | 0.96 | C55—H56 | 0.96 |
C84—H87 | 0.96 | C55—H57 | 0.96 |
C95—C98 | 1.509 (10) | C55—H58 | 0.96 |
C95—H96 | 0.97 | C51—H52 | 0.96 |
C95—H97 | 0.97 | C51—H53 | 0.96 |
C61—C63 | 1.367 (11) | C51—H54 | 0.96 |
| | | |
O112—Si1—O111 | 100.74 (19) | H71—C70—H72 | 109.5 |
O112—Si1—O110 | 106.2 (2) | C68—C70—H73 | 109.5 |
O111—Si1—O110 | 106.39 (18) | H71—C70—H73 | 109.5 |
O112—Si1—S114 | 114.44 (14) | H72—C70—H73 | 109.5 |
O111—Si1—S114 | 117.08 (15) | C102—C105—H106 | 109.5 |
O110—Si1—S114 | 110.96 (14) | C102—C105—H107 | 109.5 |
C59—O112—Si1 | 132.2 (3) | H106—C105—H107 | 109.5 |
C1—O110—Si1 | 129.7 (3) | C102—C105—H108 | 109.5 |
C30—O111—Si1 | 140.6 (4) | H106—C105—H108 | 109.5 |
C102—N109—C95 | 117.1 (6) | H107—C105—H108 | 109.5 |
C102—N109—C88 | 111.5 (6) | C7—C9—C1 | 118.1 (5) |
C95—N109—C88 | 109.8 (6) | C7—C9—C20 | 120.2 (5) |
C102—N109—H115 | 111 (4) | C1—C9—C20 | 121.6 (5) |
C95—N109—H115 | 102 (4) | C88—C91—H92 | 109.5 |
C88—N109—H115 | 105 (4) | C88—C91—H93 | 109.5 |
C36—C38—C30 | 117.5 (5) | H92—C91—H93 | 109.5 |
C36—C38—C49 | 119.9 (5) | C88—C91—H94 | 109.5 |
C30—C38—C49 | 122.6 (5) | H92—C91—H94 | 109.5 |
C84—C78—C167 | 110.0 (5) | H93—C91—H94 | 109.5 |
C84—C78—C80 | 111.1 (6) | C10—C16—H17 | 109.5 |
C167—C78—C80 | 112.6 (5) | C10—C16—H18 | 109.5 |
C84—C78—H79 | 107.6 | H17—C16—H18 | 109.5 |
C167—C78—H79 | 107.6 | C10—C16—H19 | 109.5 |
C80—C78—H79 | 107.6 | H17—C16—H19 | 109.5 |
O110—C1—C9 | 118.5 (4) | H18—C16—H19 | 109.5 |
O110—C1—C2 | 119.7 (4) | C61—C60—C59 | 118.6 (6) |
C9—C1—C2 | 121.7 (5) | C61—C60—C68 | 119.2 (6) |
C3—C5—C7 | 120.2 (5) | C59—C60—C68 | 122.1 (5) |
C3—C5—H6 | 119.9 | C34—C36—C38 | 123.0 (6) |
C7—C5—H6 | 119.9 | C34—C36—H37 | 118.5 |
C32—C31—C30 | 118.4 (6) | C38—C36—H37 | 118.5 |
C32—C31—C39 | 121.6 (6) | C91—C88—N109 | 114.2 (6) |
C30—C31—C39 | 119.9 (5) | C91—C88—H89 | 108.7 |
C3—C2—C1 | 117.3 (5) | N109—C88—H89 | 108.7 |
C3—C2—C10 | 119.4 (5) | C91—C88—H90 | 108.7 |
C1—C2—C10 | 123.3 (5) | N109—C88—H90 | 108.7 |
C31—C39—C41 | 112.9 (6) | H89—C88—H90 | 107.6 |
C31—C39—C45 | 110.5 (5) | C10—C12—H13 | 109.5 |
C41—C39—C45 | 110.0 (6) | C10—C12—H14 | 109.5 |
C31—C39—H40 | 107.7 | H13—C12—H14 | 109.5 |
C41—C39—H40 | 107.7 | C10—C12—H15 | 109.5 |
C45—C39—H40 | 107.7 | H13—C12—H15 | 109.5 |
C39—C45—H46 | 109.5 | H14—C12—H15 | 109.5 |
C39—C45—H47 | 109.5 | C167—C65—C63 | 121.7 (6) |
H46—C45—H47 | 109.5 | C167—C65—H66 | 119.2 |
C39—C45—H48 | 109.5 | C63—C65—H66 | 119.2 |
H46—C45—H48 | 109.5 | C78—C80—H81 | 109.5 |
H47—C45—H48 | 109.5 | C78—C80—H82 | 109.5 |
C2—C10—C16 | 112.0 (6) | H81—C80—H82 | 109.5 |
C2—C10—C12 | 110.6 (5) | C78—C80—H83 | 109.5 |
C16—C10—C12 | 110.6 (5) | H81—C80—H83 | 109.5 |
C2—C10—H11 | 107.8 | H82—C80—H83 | 109.5 |
C16—C10—H11 | 107.8 | C95—C98—H99 | 109.5 |
C12—C10—H11 | 107.8 | C95—C98—H100 | 109.5 |
C39—C41—H42 | 109.5 | H99—C98—H100 | 109.5 |
C39—C41—H43 | 109.5 | C95—C98—H101 | 109.5 |
H42—C41—H43 | 109.5 | H99—C98—H101 | 109.5 |
C39—C41—H44 | 109.5 | H100—C98—H101 | 109.5 |
H42—C41—H44 | 109.5 | C65—C167—C59 | 118.2 (6) |
H43—C41—H44 | 109.5 | C65—C167—C78 | 118.9 (5) |
C20—C22—H23 | 109.5 | C59—C167—C78 | 122.8 (5) |
C20—C22—H24 | 109.5 | O112—C59—C167 | 120.1 (5) |
H23—C22—H24 | 109.5 | O112—C59—C60 | 119.0 (5) |
C20—C22—H25 | 109.5 | C167—C59—C60 | 120.8 (5) |
H23—C22—H25 | 109.5 | C20—C26—H27 | 109.5 |
H24—C22—H25 | 109.5 | C20—C26—H28 | 109.5 |
C36—C34—C32 | 118.6 (6) | H27—C26—H28 | 109.5 |
C36—C34—H35 | 120.7 | C20—C26—H29 | 109.5 |
C32—C34—H35 | 120.7 | H27—C26—H29 | 109.5 |
C22—C20—C9 | 111.1 (6) | H28—C26—H29 | 109.5 |
C22—C20—C26 | 109.7 (6) | C5—C7—C9 | 121.0 (5) |
C9—C20—C26 | 114.3 (6) | C5—C7—H8 | 119.5 |
C22—C20—H21 | 107.1 | C9—C7—H8 | 119.5 |
C9—C20—H21 | 107.1 | C68—C74—H75 | 109.5 |
C26—C20—H21 | 107.1 | C68—C74—H76 | 109.5 |
C5—C3—C2 | 121.6 (6) | H75—C74—H76 | 109.5 |
C5—C3—H4 | 119.2 | C68—C74—H77 | 109.5 |
C2—C3—H4 | 119.2 | H75—C74—H77 | 109.5 |
C78—C84—H85 | 109.5 | H76—C74—H77 | 109.5 |
C78—C84—H86 | 109.5 | C61—C63—C65 | 118.9 (6) |
H85—C84—H86 | 109.5 | C61—C63—H64 | 120.6 |
C78—C84—H87 | 109.5 | C65—C63—H64 | 120.6 |
H85—C84—H87 | 109.5 | N109—C102—C105 | 112.1 (6) |
H86—C84—H87 | 109.5 | N109—C102—H103 | 109.2 |
N109—C95—C98 | 114.4 (6) | C105—C102—H103 | 109.2 |
N109—C95—H96 | 108.7 | N109—C102—H104 | 109.2 |
C98—C95—H96 | 108.7 | C105—C102—H104 | 109.2 |
N109—C95—H97 | 108.7 | H103—C102—H104 | 107.9 |
C98—C95—H97 | 108.7 | C55—C49—C38 | 112.2 (6) |
H96—C95—H97 | 107.6 | C55—C49—C51 | 109.8 (6) |
O111—C30—C38 | 120.6 (5) | C38—C49—C51 | 110.6 (6) |
O111—C30—C31 | 118.6 (5) | C55—C49—H50 | 108 |
C38—C30—C31 | 120.6 (5) | C38—C49—H50 | 108 |
C63—C61—C60 | 121.8 (7) | C51—C49—H50 | 108 |
C63—C61—H62 | 119.1 | C49—C55—H56 | 109.5 |
C60—C61—H62 | 119.1 | C49—C55—H57 | 109.5 |
C31—C32—C34 | 121.8 (6) | H56—C55—H57 | 109.5 |
C31—C32—H33 | 119.1 | C49—C55—H58 | 109.5 |
C34—C32—H33 | 119.1 | H56—C55—H58 | 109.5 |
C74—C68—C70 | 110.5 (6) | H57—C55—H58 | 109.5 |
C74—C68—C60 | 109.9 (6) | C49—C51—H52 | 109.5 |
C70—C68—C60 | 112.5 (6) | C49—C51—H53 | 109.5 |
C74—C68—H69 | 107.9 | H52—C51—H53 | 109.5 |
C70—C68—H69 | 107.9 | C49—C51—H54 | 109.5 |
C60—C68—H69 | 107.9 | H52—C51—H54 | 109.5 |
C68—C70—H71 | 109.5 | H53—C51—H54 | 109.5 |
C68—C70—H72 | 109.5 | | |
| | | |
O111—Si1—O112—C59 | −16.2 (5) | C2—C1—C9—C20 | 177.0 (5) |
O110—Si1—O112—C59 | 94.5 (5) | C22—C20—C9—C7 | 82.7 (7) |
S114—Si1—O112—C59 | −142.7 (4) | C26—C20—C9—C7 | −42.1 (8) |
O112—Si1—O110—C1 | 120.7 (4) | C22—C20—C9—C1 | −94.3 (7) |
O111—Si1—O110—C1 | −132.5 (4) | C26—C20—C9—C1 | 140.9 (6) |
S114—Si1—O110—C1 | −4.2 (5) | C63—C61—C60—C59 | 0.3 (12) |
O112—Si1—O111—C30 | 164.7 (6) | C63—C61—C60—C68 | −177.5 (8) |
O110—Si1—O111—C30 | 54.1 (6) | C74—C68—C60—C61 | 65.5 (9) |
S114—Si1—O111—C30 | −70.6 (6) | C70—C68—C60—C61 | −58.1 (9) |
Si1—O110—C1—C9 | 104.1 (5) | C74—C68—C60—C59 | −112.2 (7) |
Si1—O110—C1—C2 | −79.5 (6) | C70—C68—C60—C59 | 124.2 (7) |
O110—C1—C2—C3 | −176.2 (5) | C32—C34—C36—C38 | −1.6 (12) |
C9—C1—C2—C3 | 0.0 (8) | C30—C38—C36—C34 | 1.0 (11) |
O110—C1—C2—C10 | 2.1 (8) | C49—C38—C36—C34 | 178.5 (7) |
C9—C1—C2—C10 | 178.3 (5) | C102—N109—C88—C91 | 68.1 (9) |
C32—C31—C39—C41 | −31.2 (9) | C95—N109—C88—C91 | −160.4 (7) |
C30—C31—C39—C41 | 152.5 (6) | C63—C65—C167—C59 | −0.3 (11) |
C32—C31—C39—C45 | 92.5 (8) | C63—C65—C167—C78 | 175.9 (7) |
C30—C31—C39—C45 | −83.8 (7) | C84—C78—C167—C65 | −68.4 (8) |
C3—C2—C10—C16 | −53.1 (7) | C80—C78—C167—C65 | 56.0 (9) |
C1—C2—C10—C16 | 128.6 (6) | C84—C78—C167—C59 | 107.7 (7) |
C3—C2—C10—C12 | 70.7 (7) | C80—C78—C167—C59 | −127.9 (7) |
C1—C2—C10—C12 | −107.6 (6) | Si1—O112—C59—C167 | 80.2 (7) |
C7—C5—C3—C2 | −1.6 (10) | Si1—O112—C59—C60 | −104.0 (6) |
C1—C2—C3—C5 | 0.9 (8) | C65—C167—C59—O112 | 177.4 (6) |
C10—C2—C3—C5 | −177.6 (6) | C78—C167—C59—O112 | 1.3 (9) |
C102—N109—C95—C98 | 59.3 (9) | C65—C167—C59—C60 | 1.7 (9) |
C88—N109—C95—C98 | −69.1 (9) | C78—C167—C59—C60 | −174.5 (5) |
Si1—O111—C30—C38 | 89.3 (7) | C61—C60—C59—O112 | −177.4 (6) |
Si1—O111—C30—C31 | −94.9 (7) | C68—C60—C59—O112 | 0.3 (9) |
C36—C38—C30—O111 | 176.2 (6) | C61—C60—C59—C167 | −1.7 (9) |
C49—C38—C30—O111 | −1.2 (9) | C68—C60—C59—C167 | 176.1 (6) |
C36—C38—C30—C31 | 0.4 (9) | C3—C5—C7—C9 | 1.4 (10) |
C49—C38—C30—C31 | −177.0 (5) | C1—C9—C7—C5 | −0.6 (8) |
C32—C31—C30—O111 | −177.0 (6) | C20—C9—C7—C5 | −177.7 (6) |
C39—C31—C30—O111 | −0.6 (8) | C60—C61—C63—C65 | 1.0 (14) |
C32—C31—C30—C38 | −1.2 (9) | C167—C65—C63—C61 | −1.0 (13) |
C39—C31—C30—C38 | 175.2 (5) | C95—N109—C102—C105 | 62.2 (9) |
C30—C31—C32—C34 | 0.5 (11) | C88—N109—C102—C105 | −170.2 (7) |
C39—C31—C32—C34 | −175.8 (6) | C36—C38—C49—C55 | 68.4 (8) |
C36—C34—C32—C31 | 0.8 (12) | C30—C38—C49—C55 | −114.2 (7) |
O110—C1—C9—C7 | 176.2 (5) | C36—C38—C49—C51 | −54.6 (9) |
C2—C1—C9—C7 | −0.1 (8) | C30—C38—C49—C51 | 122.8 (6) |
O110—C1—C9—C20 | −6.8 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N109—H115···S114 | 0.80 (6) | 2.31 (7) | 3.101 (5) | 174 (5) |
Crystal data top
C36H51O3SSi·C5H6N | F(000) = 1456 |
Mr = 672.02 | Dx = 1.134 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7852 reflections |
a = 13.4301 (11) Å | θ = 3–28.5° |
b = 16.2937 (8) Å | µ = 0.15 mm−1 |
c = 18.8001 (14) Å | T = 90 K |
β = 106.835 (6)° | Plate, colorless |
V = 3937.6 (5) Å3 | 0.38 × 0.31 × 0.15 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 5724 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.039 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.1° |
rotation method scans | h = −13→16 |
21931 measured reflections | k = −19→20 |
7717 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H 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 reflections | Δρmax = 0.64 e Å−3 |
440 parameters | Δρmin = −0.51 e Å−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 | x | y | z | Uiso*/Ueq | |
S92 | 0.59663 (4) | 0.52562 (3) | 0.08971 (2) | 0.01925 (12) | |
Si91 | 0.68561 (4) | 0.51389 (3) | 0.19666 (3) | 0.01487 (12) | |
O90 | 0.62829 (10) | 0.45436 (8) | 0.24460 (7) | 0.0169 (3) | |
O88 | 0.70800 (10) | 0.59826 (8) | 0.24731 (7) | 0.0179 (3) | |
O89 | 0.80042 (10) | 0.47124 (8) | 0.20478 (7) | 0.0168 (3) | |
C60 | 0.92939 (14) | 0.48577 (12) | 0.14139 (10) | 0.0188 (4) | |
N103 | 0.40549 (14) | 0.43770 (12) | 0.10495 (9) | 0.0251 (4) | |
C65 | 0.84821 (15) | 0.35020 (13) | 0.05265 (10) | 0.0206 (4) | |
H65 | 0.8219 | 0.3049 | 0.0231 | 0.025* | |
C59 | 0.84216 (14) | 0.44379 (12) | 0.14980 (9) | 0.0156 (4) | |
C67 | 0.80149 (14) | 0.37435 (12) | 0.10706 (10) | 0.0171 (4) | |
C9 | 0.57180 (15) | 0.50596 (13) | 0.34642 (11) | 0.0227 (4) | |
C31 | 0.86545 (16) | 0.66447 (13) | 0.31481 (11) | 0.0241 (4) | |
C95 | 0.30929 (18) | 0.33332 (14) | 0.13960 (13) | 0.0322 (5) | |
H95 | 0.3066 | 0.2871 | 0.1681 | 0.039* | |
C63 | 0.93240 (16) | 0.39190 (14) | 0.04176 (10) | 0.0238 (4) | |
H63 | 0.9614 | 0.3755 | 0.0047 | 0.029* | |
C2 | 0.70613 (15) | 0.39916 (13) | 0.36697 (10) | 0.0205 (4) | |
C101 | 0.32028 (18) | 0.47031 (15) | 0.05901 (12) | 0.0316 (5) | |
H101 | 0.325 | 0.5173 | 0.0321 | 0.038* | |
C1 | 0.63700 (14) | 0.45433 (12) | 0.32033 (10) | 0.0181 (4) | |
C80 | 0.76468 (17) | 0.23924 (13) | 0.15610 (11) | 0.0243 (4) | |
H80A | 0.7921 | 0.2098 | 0.1217 | 0.037* | |
H80B | 0.7122 | 0.2067 | 0.1682 | 0.037* | |
H80C | 0.8197 | 0.2505 | 0.2006 | 0.037* | |
C78 | 0.71662 (14) | 0.32046 (12) | 0.12066 (10) | 0.0184 (4) | |
H78 | 0.6876 | 0.3487 | 0.1562 | 0.022* | |
C68 | 0.97703 (16) | 0.55789 (13) | 0.18999 (12) | 0.0235 (4) | |
H68 | 0.942 | 0.5626 | 0.2289 | 0.028* | |
C10 | 0.77082 (16) | 0.33850 (13) | 0.33762 (11) | 0.0240 (4) | |
H10 | 0.7587 | 0.3498 | 0.2846 | 0.029* | |
C61 | 0.97288 (15) | 0.45837 (13) | 0.08669 (11) | 0.0217 (4) | |
H61 | 1.0306 | 0.4855 | 0.0802 | 0.026* | |
C7 | 0.57957 (18) | 0.50193 (15) | 0.42215 (12) | 0.0315 (5) | |
H7 | 0.537 | 0.5354 | 0.4409 | 0.038* | |
C3 | 0.71076 (17) | 0.39873 (15) | 0.44233 (11) | 0.0276 (5) | |
H3 | 0.7567 | 0.3633 | 0.4745 | 0.033* | |
C32 | 0.93165 (16) | 0.73163 (14) | 0.32309 (12) | 0.0285 (5) | |
H32 | 0.9926 | 0.7325 | 0.3623 | 0.034* | |
C93 | 0.40237 (17) | 0.37079 (15) | 0.14476 (12) | 0.0300 (5) | |
H93 | 0.4636 | 0.3494 | 0.1762 | 0.036* | |
C38 | 0.74883 (16) | 0.73069 (13) | 0.20427 (11) | 0.0230 (4) | |
C30 | 0.77479 (15) | 0.66443 (12) | 0.25379 (10) | 0.0197 (4) | |
C29 | 0.38266 (16) | 0.53717 (15) | 0.28616 (13) | 0.0308 (5) | |
H29A | 0.3729 | 0.4819 | 0.2678 | 0.046* | |
H29B | 0.3358 | 0.573 | 0.2516 | 0.046* | |
H29C | 0.3689 | 0.5399 | 0.3334 | 0.046* | |
C49 | 0.64837 (17) | 0.73373 (14) | 0.14014 (12) | 0.0283 (5) | |
H49 | 0.6141 | 0.6804 | 0.1387 | 0.034* | |
C20 | 0.49448 (16) | 0.56366 (14) | 0.29507 (12) | 0.0261 (5) | |
H20 | 0.5061 | 0.561 | 0.246 | 0.031* | |
C39 | 0.88707 (17) | 0.59522 (14) | 0.37117 (12) | 0.0298 (5) | |
H39 | 0.8554 | 0.5453 | 0.3452 | 0.036* | |
C99 | 0.22541 (18) | 0.43448 (18) | 0.05136 (12) | 0.0381 (6) | |
H99 | 0.1654 | 0.4569 | 0.0193 | 0.046* | |
C36 | 0.81811 (18) | 0.79664 (14) | 0.21618 (13) | 0.0296 (5) | |
H36 | 0.8027 | 0.8414 | 0.1841 | 0.036* | |
C16 | 0.7363 (2) | 0.25072 (15) | 0.34485 (13) | 0.0336 (5) | |
H16A | 0.7465 | 0.2381 | 0.3963 | 0.05* | |
H16B | 0.7768 | 0.2137 | 0.3247 | 0.05* | |
H16C | 0.664 | 0.2449 | 0.3181 | 0.05* | |
C97 | 0.21980 (17) | 0.36500 (16) | 0.09166 (12) | 0.0331 (5) | |
H97 | 0.1561 | 0.3397 | 0.0866 | 0.04* | |
C5 | 0.64865 (19) | 0.44976 (16) | 0.46993 (12) | 0.0334 (5) | |
H5 | 0.6533 | 0.449 | 0.5202 | 0.04* | |
C84 | 0.62745 (16) | 0.30375 (14) | 0.05008 (11) | 0.0245 (4) | |
H84A | 0.5969 | 0.3549 | 0.0293 | 0.037* | |
H84B | 0.5757 | 0.2705 | 0.0622 | 0.037* | |
H84C | 0.6539 | 0.2755 | 0.0146 | 0.037* | |
C22 | 0.51228 (19) | 0.65215 (16) | 0.32222 (16) | 0.0422 (6) | |
H22A | 0.5032 | 0.6562 | 0.3709 | 0.063* | |
H22B | 0.4632 | 0.6873 | 0.2886 | 0.063* | |
H22C | 0.5817 | 0.6686 | 0.3242 | 0.063* | |
C34 | 0.90890 (18) | 0.79728 (14) | 0.27421 (13) | 0.0329 (5) | |
H34 | 0.9545 | 0.8415 | 0.2804 | 0.039* | |
C51 | 0.6675 (2) | 0.7454 (3) | 0.06600 (15) | 0.0678 (10) | |
H51A | 0.6964 | 0.799 | 0.0639 | 0.102* | |
H51B | 0.603 | 0.7404 | 0.0273 | 0.102* | |
H51C | 0.7154 | 0.7044 | 0.0594 | 0.102* | |
C70 | 0.9590 (3) | 0.63752 (16) | 0.14621 (16) | 0.0512 (8) | |
H70A | 0.9967 | 0.6363 | 0.11 | 0.077* | |
H70B | 0.9827 | 0.6828 | 0.1795 | 0.077* | |
H70C | 0.886 | 0.6438 | 0.1215 | 0.077* | |
C12 | 0.88668 (19) | 0.34763 (18) | 0.3753 (2) | 0.0566 (9) | |
H12A | 0.908 | 0.4026 | 0.3684 | 0.085* | |
H12B | 0.9243 | 0.3095 | 0.3539 | 0.085* | |
H12C | 0.901 | 0.3366 | 0.4275 | 0.085* | |
C41 | 0.83510 (19) | 0.61267 (18) | 0.43164 (14) | 0.0417 (6) | |
H41A | 0.8658 | 0.6606 | 0.459 | 0.063* | |
H41B | 0.8446 | 0.5666 | 0.4647 | 0.063* | |
H41C | 0.7621 | 0.6219 | 0.4093 | 0.063* | |
C55 | 0.5739 (2) | 0.7983 (2) | 0.15327 (18) | 0.0664 (10) | |
H55A | 0.5552 | 0.785 | 0.1975 | 0.1* | |
H55B | 0.5125 | 0.7997 | 0.1116 | 0.1* | |
H55C | 0.6071 | 0.8511 | 0.1591 | 0.1* | |
C45 | 1.00251 (19) | 0.57803 (18) | 0.40586 (14) | 0.0418 (6) | |
H45A | 1.0352 | 0.5698 | 0.3673 | 0.063* | |
H45B | 1.0108 | 0.5296 | 0.4361 | 0.063* | |
H45C | 1.0343 | 0.6238 | 0.4361 | 0.063* | |
C74 | 1.09251 (19) | 0.54464 (19) | 0.22824 (19) | 0.0580 (9) | |
H74A | 1.1017 | 0.4957 | 0.2578 | 0.087* | |
H74B | 1.1197 | 0.5908 | 0.2596 | 0.087* | |
H74C | 1.1288 | 0.5391 | 0.1914 | 0.087* | |
H103 | 0.469 (3) | 0.461 (2) | 0.1066 (17) | 0.062 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S92 | 0.0183 (2) | 0.0209 (3) | 0.0177 (2) | −0.00266 (19) | 0.00388 (17) | 0.00065 (18) |
Si91 | 0.0122 (2) | 0.0165 (3) | 0.0164 (2) | −0.0012 (2) | 0.00498 (18) | −0.00077 (19) |
O90 | 0.0151 (6) | 0.0199 (7) | 0.0167 (6) | −0.0007 (5) | 0.0064 (5) | 0.0001 (5) |
O88 | 0.0138 (6) | 0.0188 (7) | 0.0208 (6) | −0.0017 (5) | 0.0047 (5) | −0.0039 (5) |
O89 | 0.0139 (6) | 0.0205 (7) | 0.0173 (6) | −0.0002 (5) | 0.0064 (5) | −0.0023 (5) |
C60 | 0.0155 (9) | 0.0197 (10) | 0.0216 (9) | 0.0018 (8) | 0.0064 (7) | 0.0046 (8) |
N103 | 0.0241 (9) | 0.0279 (10) | 0.0265 (9) | −0.0025 (8) | 0.0126 (7) | 0.0005 (7) |
C65 | 0.0224 (10) | 0.0226 (11) | 0.0172 (9) | 0.0015 (8) | 0.0064 (7) | −0.0011 (7) |
C59 | 0.0143 (9) | 0.0174 (9) | 0.0159 (8) | 0.0027 (7) | 0.0057 (7) | 0.0024 (7) |
C67 | 0.0158 (9) | 0.0187 (10) | 0.0171 (8) | 0.0015 (7) | 0.0051 (7) | 0.0026 (7) |
C9 | 0.0175 (9) | 0.0257 (11) | 0.0279 (10) | −0.0005 (8) | 0.0112 (8) | −0.0005 (8) |
C31 | 0.0182 (10) | 0.0220 (11) | 0.0309 (10) | 0.0022 (8) | 0.0053 (8) | −0.0078 (8) |
C95 | 0.0294 (12) | 0.0262 (12) | 0.0427 (13) | −0.0013 (9) | 0.0132 (10) | 0.0107 (10) |
C63 | 0.0226 (10) | 0.0329 (12) | 0.0198 (9) | 0.0041 (9) | 0.0121 (8) | 0.0036 (8) |
C2 | 0.0175 (9) | 0.0247 (11) | 0.0207 (9) | 0.0003 (8) | 0.0075 (7) | 0.0017 (8) |
C101 | 0.0365 (12) | 0.0364 (13) | 0.0288 (11) | 0.0098 (10) | 0.0204 (10) | 0.0126 (9) |
C1 | 0.0140 (9) | 0.0240 (11) | 0.0172 (8) | −0.0038 (8) | 0.0056 (7) | −0.0006 (7) |
C80 | 0.0271 (11) | 0.0196 (11) | 0.0285 (10) | −0.0010 (8) | 0.0114 (8) | 0.0017 (8) |
C78 | 0.0170 (9) | 0.0193 (10) | 0.0193 (9) | −0.0009 (8) | 0.0060 (7) | −0.0003 (7) |
C68 | 0.0196 (10) | 0.0202 (11) | 0.0339 (10) | −0.0027 (8) | 0.0128 (8) | −0.0008 (9) |
C10 | 0.0239 (10) | 0.0252 (11) | 0.0239 (10) | 0.0060 (8) | 0.0084 (8) | 0.0052 (8) |
C61 | 0.0169 (9) | 0.0272 (11) | 0.0243 (9) | 0.0004 (8) | 0.0112 (8) | 0.0070 (8) |
C7 | 0.0311 (12) | 0.0394 (14) | 0.0305 (11) | 0.0026 (10) | 0.0191 (9) | −0.0051 (10) |
C3 | 0.0253 (11) | 0.0351 (13) | 0.0217 (10) | 0.0015 (9) | 0.0059 (8) | 0.0056 (9) |
C32 | 0.0169 (10) | 0.0278 (12) | 0.0382 (12) | −0.0011 (8) | 0.0037 (9) | −0.0117 (9) |
C93 | 0.0217 (11) | 0.0326 (13) | 0.0337 (11) | 0.0021 (9) | 0.0049 (9) | 0.0087 (9) |
C38 | 0.0230 (10) | 0.0187 (11) | 0.0282 (10) | 0.0017 (8) | 0.0087 (8) | −0.0043 (8) |
C30 | 0.0163 (9) | 0.0196 (10) | 0.0248 (9) | −0.0014 (8) | 0.0084 (8) | −0.0066 (8) |
C29 | 0.0214 (11) | 0.0290 (12) | 0.0425 (12) | 0.0002 (9) | 0.0102 (9) | −0.0021 (10) |
C49 | 0.0301 (12) | 0.0220 (11) | 0.0282 (10) | 0.0008 (9) | 0.0013 (9) | −0.0003 (9) |
C20 | 0.0193 (10) | 0.0282 (12) | 0.0342 (11) | 0.0054 (9) | 0.0129 (9) | 0.0016 (9) |
C39 | 0.0243 (11) | 0.0280 (12) | 0.0300 (11) | −0.0001 (9) | −0.0035 (9) | −0.0033 (9) |
C99 | 0.0230 (11) | 0.0642 (18) | 0.0297 (11) | 0.0148 (11) | 0.0115 (9) | 0.0180 (11) |
C36 | 0.0343 (12) | 0.0189 (11) | 0.0376 (12) | −0.0028 (9) | 0.0136 (10) | −0.0016 (9) |
C16 | 0.0408 (13) | 0.0297 (13) | 0.0324 (11) | −0.0006 (10) | 0.0141 (10) | 0.0011 (10) |
C97 | 0.0191 (10) | 0.0477 (15) | 0.0347 (11) | −0.0034 (10) | 0.0110 (9) | 0.0017 (10) |
C5 | 0.0371 (13) | 0.0457 (15) | 0.0199 (10) | −0.0008 (11) | 0.0123 (9) | 0.0004 (9) |
C84 | 0.0219 (10) | 0.0263 (11) | 0.0259 (10) | −0.0045 (8) | 0.0078 (8) | −0.0019 (8) |
C22 | 0.0255 (12) | 0.0286 (13) | 0.0684 (17) | 0.0017 (10) | 0.0072 (11) | −0.0023 (12) |
C34 | 0.0276 (11) | 0.0257 (12) | 0.0491 (13) | −0.0096 (9) | 0.0168 (10) | −0.0127 (10) |
C51 | 0.0452 (17) | 0.118 (3) | 0.0364 (14) | −0.0001 (19) | 0.0059 (12) | 0.0150 (17) |
C70 | 0.097 (2) | 0.0221 (13) | 0.0524 (15) | −0.0009 (14) | 0.0501 (16) | −0.0010 (11) |
C12 | 0.0229 (13) | 0.0400 (16) | 0.106 (2) | 0.0053 (11) | 0.0165 (14) | −0.0235 (16) |
C41 | 0.0299 (13) | 0.0535 (17) | 0.0394 (13) | 0.0019 (12) | 0.0062 (10) | 0.0107 (12) |
C55 | 0.0334 (15) | 0.093 (3) | 0.0588 (18) | 0.0227 (16) | −0.0086 (13) | −0.0243 (18) |
C45 | 0.0309 (13) | 0.0511 (17) | 0.0369 (13) | 0.0141 (11) | −0.0007 (10) | 0.0017 (11) |
C74 | 0.0194 (12) | 0.0539 (19) | 0.093 (2) | −0.0052 (12) | 0.0034 (13) | −0.0424 (17) |
Geometric parameters (Å, º) top
S92—Si91 | 2.0286 (7) | C93—H93 | 0.93 |
Si91—O88 | 1.6496 (14) | C38—C36 | 1.396 (3) |
Si91—O89 | 1.6576 (13) | C38—C30 | 1.402 (3) |
Si91—O90 | 1.6576 (13) | C38—C49 | 1.528 (3) |
O90—C1 | 1.394 (2) | C29—C20 | 1.525 (3) |
O88—C30 | 1.385 (2) | C29—H29A | 0.96 |
O89—C59 | 1.385 (2) | C29—H29B | 0.96 |
C60—C61 | 1.395 (3) | C29—H29C | 0.96 |
C60—C59 | 1.405 (3) | C49—C51 | 1.501 (4) |
C60—C68 | 1.512 (3) | C49—C55 | 1.520 (4) |
N103—C101 | 1.329 (3) | C49—H49 | 0.98 |
N103—C93 | 1.330 (3) | C20—C22 | 1.525 (3) |
N103—H103 | 0.93 (3) | C20—H20 | 0.98 |
C65—C63 | 1.384 (3) | C39—C41 | 1.523 (3) |
C65—C67 | 1.402 (3) | C39—C45 | 1.524 (3) |
C65—H65 | 0.93 | C39—H39 | 0.98 |
C59—C67 | 1.404 (3) | C99—C97 | 1.376 (3) |
C67—C78 | 1.518 (3) | C99—H99 | 0.93 |
C9—C7 | 1.399 (3) | C36—C34 | 1.381 (3) |
C9—C1 | 1.401 (3) | C36—H36 | 0.93 |
C9—C20 | 1.521 (3) | C16—H16A | 0.96 |
C31—C32 | 1.390 (3) | C16—H16B | 0.96 |
C31—C30 | 1.410 (3) | C16—H16C | 0.96 |
C31—C39 | 1.517 (3) | C97—H97 | 0.93 |
C95—C93 | 1.369 (3) | C5—H5 | 0.93 |
C95—C97 | 1.377 (3) | C84—H84A | 0.96 |
C95—H95 | 0.93 | C84—H84B | 0.96 |
C63—C61 | 1.384 (3) | C84—H84C | 0.96 |
C63—H63 | 0.93 | C22—H22A | 0.96 |
C2—C3 | 1.400 (3) | C22—H22B | 0.96 |
C2—C1 | 1.403 (3) | C22—H22C | 0.96 |
C2—C10 | 1.521 (3) | C34—H34 | 0.93 |
C101—C99 | 1.371 (3) | C51—H51A | 0.96 |
C101—H101 | 0.93 | C51—H51B | 0.96 |
C80—C78 | 1.537 (3) | C51—H51C | 0.96 |
C80—H80A | 0.96 | C70—H70A | 0.96 |
C80—H80B | 0.96 | C70—H70B | 0.96 |
C80—H80C | 0.96 | C70—H70C | 0.96 |
C78—C84 | 1.532 (3) | C12—H12A | 0.96 |
C78—H78 | 0.98 | C12—H12B | 0.96 |
C68—C70 | 1.518 (3) | C12—H12C | 0.96 |
C68—C74 | 1.524 (3) | C41—H41A | 0.96 |
C68—H68 | 0.98 | C41—H41B | 0.96 |
C10—C12 | 1.519 (3) | C41—H41C | 0.96 |
C10—C16 | 1.521 (3) | C55—H55A | 0.96 |
C10—H10 | 0.98 | C55—H55B | 0.96 |
C61—H61 | 0.93 | C55—H55C | 0.96 |
C7—C5 | 1.381 (3) | C45—H45A | 0.96 |
C7—H7 | 0.93 | C45—H45B | 0.96 |
C3—C5 | 1.381 (3) | C45—H45C | 0.96 |
C3—H3 | 0.93 | C74—H74A | 0.96 |
C32—C34 | 1.385 (3) | C74—H74B | 0.96 |
C32—H32 | 0.93 | C74—H74C | 0.96 |
| | | |
O88—Si91—O89 | 106.67 (7) | H29B—C29—H29C | 109.5 |
O88—Si91—O90 | 102.09 (7) | C51—C49—C55 | 111.1 (2) |
O89—Si91—O90 | 105.70 (7) | C51—C49—C38 | 112.8 (2) |
O88—Si91—S92 | 116.76 (5) | C55—C49—C38 | 111.48 (19) |
O89—Si91—S92 | 113.33 (5) | C51—C49—H49 | 107 |
O90—Si91—S92 | 111.16 (5) | C55—C49—H49 | 107 |
C1—O90—Si91 | 129.83 (12) | C38—C49—H49 | 107 |
C30—O88—Si91 | 134.80 (12) | C9—C20—C29 | 111.37 (18) |
C59—O89—Si91 | 129.30 (11) | C9—C20—C22 | 111.10 (19) |
C61—C60—C59 | 117.91 (18) | C29—C20—C22 | 111.00 (18) |
C61—C60—C68 | 120.00 (17) | C9—C20—H20 | 107.7 |
C59—C60—C68 | 122.09 (17) | C29—C20—H20 | 107.7 |
C101—N103—C93 | 122.1 (2) | C22—C20—H20 | 107.7 |
C101—N103—H103 | 118 (2) | C31—C39—C41 | 110.24 (19) |
C93—N103—H103 | 120 (2) | C31—C39—C45 | 113.6 (2) |
C63—C65—C67 | 121.83 (19) | C41—C39—C45 | 110.14 (18) |
C63—C65—H65 | 119.1 | C31—C39—H39 | 107.5 |
C67—C65—H65 | 119.1 | C41—C39—H39 | 107.5 |
O89—C59—C67 | 120.87 (16) | C45—C39—H39 | 107.5 |
O89—C59—C60 | 117.24 (16) | C101—C99—C97 | 119.3 (2) |
C67—C59—C60 | 121.81 (17) | C101—C99—H99 | 120.3 |
C65—C67—C59 | 117.49 (17) | C97—C99—H99 | 120.3 |
C65—C67—C78 | 118.49 (17) | C34—C36—C38 | 121.8 (2) |
C59—C67—C78 | 123.82 (16) | C34—C36—H36 | 119.1 |
C7—C9—C1 | 117.27 (19) | C38—C36—H36 | 119.1 |
C7—C9—C20 | 120.73 (19) | C10—C16—H16A | 109.5 |
C1—C9—C20 | 122.00 (18) | C10—C16—H16B | 109.5 |
C32—C31—C30 | 117.7 (2) | H16A—C16—H16B | 109.5 |
C32—C31—C39 | 121.36 (19) | C10—C16—H16C | 109.5 |
C30—C31—C39 | 120.88 (19) | H16A—C16—H16C | 109.5 |
C93—C95—C97 | 119.0 (2) | H16B—C16—H16C | 109.5 |
C93—C95—H95 | 120.5 | C99—C97—C95 | 119.5 (2) |
C97—C95—H95 | 120.5 | C99—C97—H97 | 120.3 |
C61—C63—C65 | 119.15 (18) | C95—C97—H97 | 120.3 |
C61—C63—H63 | 120.4 | C3—C5—C7 | 119.43 (19) |
C65—C63—H63 | 120.4 | C3—C5—H5 | 120.3 |
C3—C2—C1 | 117.59 (18) | C7—C5—H5 | 120.3 |
C3—C2—C10 | 120.08 (18) | C78—C84—H84A | 109.5 |
C1—C2—C10 | 122.26 (17) | C78—C84—H84B | 109.5 |
N103—C101—C99 | 119.8 (2) | H84A—C84—H84B | 109.5 |
N103—C101—H101 | 120.1 | C78—C84—H84C | 109.5 |
C99—C101—H101 | 120.1 | H84A—C84—H84C | 109.5 |
O90—C1—C9 | 118.75 (17) | H84B—C84—H84C | 109.5 |
O90—C1—C2 | 118.89 (17) | C20—C22—H22A | 109.5 |
C9—C1—C2 | 122.24 (17) | C20—C22—H22B | 109.5 |
C78—C80—H80A | 109.5 | H22A—C22—H22B | 109.5 |
C78—C80—H80B | 109.5 | C20—C22—H22C | 109.5 |
H80A—C80—H80B | 109.5 | H22A—C22—H22C | 109.5 |
C78—C80—H80C | 109.5 | H22B—C22—H22C | 109.5 |
H80A—C80—H80C | 109.5 | C36—C34—C32 | 119.5 (2) |
H80B—C80—H80C | 109.5 | C36—C34—H34 | 120.2 |
C67—C78—C84 | 113.18 (16) | C32—C34—H34 | 120.2 |
C67—C78—C80 | 109.24 (16) | C49—C51—H51A | 109.5 |
C84—C78—C80 | 110.31 (17) | C49—C51—H51B | 109.5 |
C67—C78—H78 | 108 | H51A—C51—H51B | 109.5 |
C84—C78—H78 | 108 | C49—C51—H51C | 109.5 |
C80—C78—H78 | 108 | H51A—C51—H51C | 109.5 |
C60—C68—C70 | 111.31 (19) | H51B—C51—H51C | 109.5 |
C60—C68—C74 | 111.69 (18) | C68—C70—H70A | 109.5 |
C70—C68—C74 | 111.0 (2) | C68—C70—H70B | 109.5 |
C60—C68—H68 | 107.5 | H70A—C70—H70B | 109.5 |
C70—C68—H68 | 107.5 | C68—C70—H70C | 109.5 |
C74—C68—H68 | 107.5 | H70A—C70—H70C | 109.5 |
C12—C10—C2 | 112.49 (19) | H70B—C70—H70C | 109.5 |
C12—C10—C16 | 110.3 (2) | C10—C12—H12A | 109.5 |
C2—C10—C16 | 110.97 (18) | C10—C12—H12B | 109.5 |
C12—C10—H10 | 107.6 | H12A—C12—H12B | 109.5 |
C2—C10—H10 | 107.6 | C10—C12—H12C | 109.5 |
C16—C10—H10 | 107.6 | H12A—C12—H12C | 109.5 |
C63—C61—C60 | 121.73 (18) | H12B—C12—H12C | 109.5 |
C63—C61—H61 | 119.1 | C39—C41—H41A | 109.5 |
C60—C61—H61 | 119.1 | C39—C41—H41B | 109.5 |
C5—C7—C9 | 121.9 (2) | H41A—C41—H41B | 109.5 |
C5—C7—H7 | 119 | C39—C41—H41C | 109.5 |
C9—C7—H7 | 119 | H41A—C41—H41C | 109.5 |
C5—C3—C2 | 121.5 (2) | H41B—C41—H41C | 109.5 |
C5—C3—H3 | 119.2 | C49—C55—H55A | 109.5 |
C2—C3—H3 | 119.2 | C49—C55—H55B | 109.5 |
C34—C32—C31 | 121.5 (2) | H55A—C55—H55B | 109.5 |
C34—C32—H32 | 119.2 | C49—C55—H55C | 109.5 |
C31—C32—H32 | 119.2 | H55A—C55—H55C | 109.5 |
N103—C93—C95 | 120.2 (2) | H55B—C55—H55C | 109.5 |
N103—C93—H93 | 119.9 | C39—C45—H45A | 109.5 |
C95—C93—H93 | 119.9 | C39—C45—H45B | 109.5 |
C36—C38—C30 | 117.39 (19) | H45A—C45—H45B | 109.5 |
C36—C38—C49 | 119.79 (19) | C39—C45—H45C | 109.5 |
C30—C38—C49 | 122.81 (19) | H45A—C45—H45C | 109.5 |
O88—C30—C38 | 120.71 (17) | H45B—C45—H45C | 109.5 |
O88—C30—C31 | 117.16 (18) | C68—C74—H74A | 109.5 |
C38—C30—C31 | 121.99 (19) | C68—C74—H74B | 109.5 |
C20—C29—H29A | 109.5 | H74A—C74—H74B | 109.5 |
C20—C29—H29B | 109.5 | C68—C74—H74C | 109.5 |
H29A—C29—H29B | 109.5 | H74A—C74—H74C | 109.5 |
C20—C29—H29C | 109.5 | H74B—C74—H74C | 109.5 |
H29A—C29—H29C | 109.5 | | |
| | | |
O88—Si91—O90—C1 | −26.71 (16) | C1—C2—C10—C16 | −112.6 (2) |
O89—Si91—O90—C1 | 84.70 (16) | C65—C63—C61—C60 | −1.7 (3) |
S92—Si91—O90—C1 | −151.93 (14) | C59—C60—C61—C63 | −0.1 (3) |
O89—Si91—O88—C30 | 49.06 (18) | C68—C60—C61—C63 | 179.12 (18) |
O90—Si91—O88—C30 | 159.74 (17) | C1—C9—C7—C5 | 0.3 (3) |
S92—Si91—O88—C30 | −78.83 (18) | C20—C9—C7—C5 | 179.6 (2) |
O88—Si91—O89—C59 | −129.62 (15) | C1—C2—C3—C5 | 0.9 (3) |
O90—Si91—O89—C59 | 122.24 (15) | C10—C2—C3—C5 | −176.2 (2) |
S92—Si91—O89—C59 | 0.25 (17) | C30—C31—C32—C34 | 1.3 (3) |
Si91—O89—C59—C67 | −69.1 (2) | C39—C31—C32—C34 | −176.0 (2) |
Si91—O89—C59—C60 | 113.98 (17) | C101—N103—C93—C95 | −0.3 (3) |
C61—C60—C59—O89 | 179.42 (16) | C97—C95—C93—N103 | 1.3 (4) |
C68—C60—C59—O89 | 0.2 (3) | Si91—O88—C30—C38 | 83.4 (2) |
C61—C60—C59—C67 | 2.5 (3) | Si91—O88—C30—C31 | −100.8 (2) |
C68—C60—C59—C67 | −176.72 (18) | C36—C38—C30—O88 | 177.44 (17) |
C63—C65—C67—C59 | 1.1 (3) | C49—C38—C30—O88 | −1.3 (3) |
C63—C65—C67—C78 | −173.97 (18) | C36—C38—C30—C31 | 1.9 (3) |
O89—C59—C67—C65 | −179.76 (16) | C49—C38—C30—C31 | −176.86 (19) |
C60—C59—C67—C65 | −3.0 (3) | C32—C31—C30—O88 | −178.25 (17) |
O89—C59—C67—C78 | −5.0 (3) | C39—C31—C30—O88 | −0.9 (3) |
C60—C59—C67—C78 | 171.79 (17) | C32—C31—C30—C38 | −2.5 (3) |
C67—C65—C63—C61 | 1.2 (3) | C39—C31—C30—C38 | 174.83 (18) |
C93—N103—C101—C99 | −0.3 (3) | C36—C38—C49—C51 | 57.8 (3) |
Si91—O90—C1—C9 | 87.2 (2) | C30—C38—C49—C51 | −123.5 (3) |
Si91—O90—C1—C2 | −96.7 (2) | C36—C38—C49—C55 | −68.0 (3) |
C7—C9—C1—O90 | 177.42 (18) | C30—C38—C49—C55 | 110.6 (3) |
C20—C9—C1—O90 | −1.9 (3) | C7—C9—C20—C29 | −67.5 (3) |
C7—C9—C1—C2 | 1.4 (3) | C1—C9—C20—C29 | 111.9 (2) |
C20—C9—C1—C2 | −177.96 (19) | C7—C9—C20—C22 | 56.9 (3) |
C3—C2—C1—O90 | −178.01 (17) | C1—C9—C20—C22 | −123.8 (2) |
C10—C2—C1—O90 | −0.9 (3) | C32—C31—C39—C41 | 90.4 (2) |
C3—C2—C1—C9 | −2.0 (3) | C30—C31—C39—C41 | −86.8 (2) |
C10—C2—C1—C9 | 175.16 (19) | C32—C31—C39—C45 | −33.8 (3) |
C65—C67—C78—C84 | −54.7 (2) | C30—C31—C39—C45 | 149.0 (2) |
C59—C67—C78—C84 | 130.57 (19) | N103—C101—C99—C97 | 0.1 (4) |
C65—C67—C78—C80 | 68.6 (2) | C30—C38—C36—C34 | 0.0 (3) |
C59—C67—C78—C80 | −106.1 (2) | C49—C38—C36—C34 | 178.8 (2) |
C61—C60—C68—C70 | 70.3 (2) | C101—C99—C97—C95 | 0.8 (4) |
C59—C60—C68—C70 | −110.5 (2) | C93—C95—C97—C99 | −1.5 (4) |
C61—C60—C68—C74 | −54.4 (3) | C2—C3—C5—C7 | 0.6 (4) |
C59—C60—C68—C74 | 124.8 (2) | C9—C7—C5—C3 | −1.3 (4) |
C3—C2—C10—C12 | −59.8 (3) | C38—C36—C34—C32 | −1.2 (3) |
C1—C2—C10—C12 | 123.2 (2) | C31—C32—C34—C36 | 0.5 (3) |
C3—C2—C10—C16 | 64.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N103—H103···S92 | 0.93 (3) | 2.11 (3) | 3.0247 (19) | 168 (3) |
Crystal data top
C36H51O3SSi·C5H6N | F(000) = 1456 |
Mr = 672.02 | Dx = 1.13 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 14027 reflections |
a = 13.4487 (12) Å | θ = 3.4–29.5° |
b = 16.3096 (9) Å | µ = 0.15 mm−1 |
c = 18.8302 (16) Å | T = 120 K |
β = 106.902 (6)° | Plate, colorless |
V = 3951.9 (5) Å3 | 0.38 × 0.31 × 0.15 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 5636 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.043 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26°, θmin = 3.1° |
rotation method scans | h = −13→16 |
21998 measured reflections | k = −19→20 |
7735 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H 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 reflections | Δρmax = 0.47 e Å−3 |
440 parameters | Δρmin = −0.50 e Å−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 | x | y | z | Uiso*/Ueq | |
S92 | 0.59619 (4) | 0.52584 (3) | 0.08988 (3) | 0.02097 (12) | |
Si91 | 0.68571 (4) | 0.51450 (3) | 0.19661 (3) | 0.01572 (12) | |
O90 | 0.62886 (10) | 0.45533 (8) | 0.24479 (7) | 0.0179 (3) | |
O88 | 0.70847 (10) | 0.59904 (8) | 0.24690 (7) | 0.0196 (3) | |
O89 | 0.80028 (10) | 0.47174 (8) | 0.20454 (7) | 0.0180 (3) | |
C60 | 0.92897 (14) | 0.48603 (12) | 0.14101 (11) | 0.0196 (4) | |
N103 | 0.40553 (15) | 0.43763 (12) | 0.10493 (10) | 0.0292 (4) | |
C65 | 0.84730 (16) | 0.35089 (13) | 0.05268 (10) | 0.0224 (4) | |
H65 | 0.8207 | 0.3058 | 0.023 | 0.027* | |
C59 | 0.84171 (14) | 0.44446 (12) | 0.14966 (10) | 0.0165 (4) | |
C67 | 0.80110 (15) | 0.37467 (12) | 0.10676 (10) | 0.0185 (4) | |
C9 | 0.57250 (16) | 0.50676 (14) | 0.34617 (12) | 0.0256 (5) | |
C31 | 0.86533 (16) | 0.66458 (14) | 0.31475 (12) | 0.0261 (5) | |
C95 | 0.30962 (18) | 0.33418 (15) | 0.14080 (14) | 0.0373 (6) | |
H95 | 0.3069 | 0.2885 | 0.1698 | 0.045* | |
C63 | 0.93157 (17) | 0.39217 (14) | 0.04175 (11) | 0.0264 (5) | |
H63 | 0.9605 | 0.3755 | 0.0048 | 0.032* | |
C2 | 0.70659 (16) | 0.40000 (13) | 0.36705 (11) | 0.0237 (4) | |
C101 | 0.3207 (2) | 0.47000 (16) | 0.05921 (13) | 0.0371 (6) | |
H101 | 0.3253 | 0.5168 | 0.0321 | 0.045* | |
C1 | 0.63759 (15) | 0.45528 (13) | 0.32044 (10) | 0.0197 (4) | |
C80 | 0.76433 (18) | 0.23999 (13) | 0.15608 (12) | 0.0283 (5) | |
H80A | 0.7911 | 0.2103 | 0.1216 | 0.042* | |
H80B | 0.7121 | 0.2077 | 0.1686 | 0.042* | |
H80C | 0.8198 | 0.2513 | 0.2002 | 0.042* | |
C78 | 0.71631 (15) | 0.32100 (13) | 0.12069 (11) | 0.0210 (4) | |
H78 | 0.6877 | 0.3494 | 0.1562 | 0.025* | |
C68 | 0.97654 (16) | 0.55822 (13) | 0.18936 (13) | 0.0268 (5) | |
H68 | 0.9412 | 0.5632 | 0.2279 | 0.032* | |
C10 | 0.77067 (17) | 0.33940 (14) | 0.33764 (12) | 0.0271 (5) | |
H10 | 0.7581 | 0.3506 | 0.2846 | 0.032* | |
C61 | 0.97215 (16) | 0.45847 (13) | 0.08650 (11) | 0.0239 (4) | |
H61 | 1.0299 | 0.4854 | 0.08 | 0.029* | |
C7 | 0.57995 (19) | 0.50288 (16) | 0.42178 (13) | 0.0369 (6) | |
H7 | 0.5374 | 0.5363 | 0.4404 | 0.044* | |
C3 | 0.71083 (18) | 0.39964 (16) | 0.44189 (12) | 0.0332 (5) | |
H3 | 0.7565 | 0.3641 | 0.4741 | 0.04* | |
C32 | 0.93201 (17) | 0.73172 (15) | 0.32306 (14) | 0.0330 (5) | |
H32 | 0.993 | 0.7324 | 0.3623 | 0.04* | |
C93 | 0.40267 (18) | 0.37125 (16) | 0.14537 (13) | 0.0353 (5) | |
H93 | 0.4639 | 0.35 | 0.1768 | 0.042* | |
C38 | 0.75011 (17) | 0.73100 (13) | 0.20394 (12) | 0.0261 (5) | |
C30 | 0.77527 (15) | 0.66493 (13) | 0.25339 (11) | 0.0212 (4) | |
C29 | 0.38329 (18) | 0.53786 (16) | 0.28638 (15) | 0.0377 (6) | |
H29A | 0.3737 | 0.4823 | 0.2688 | 0.057* | |
H29B | 0.3365 | 0.5732 | 0.2514 | 0.057* | |
H29C | 0.3694 | 0.5414 | 0.3335 | 0.057* | |
C49 | 0.65018 (19) | 0.73397 (14) | 0.13965 (12) | 0.0318 (5) | |
H49 | 0.6168 | 0.6802 | 0.1373 | 0.038* | |
C20 | 0.49506 (17) | 0.56426 (14) | 0.29517 (13) | 0.0303 (5) | |
H20 | 0.5063 | 0.5615 | 0.2461 | 0.036* | |
C39 | 0.88655 (18) | 0.59586 (15) | 0.37126 (13) | 0.0340 (5) | |
H39 | 0.8542 | 0.5461 | 0.3456 | 0.041* | |
C99 | 0.22594 (19) | 0.4340 (2) | 0.05199 (14) | 0.0449 (7) | |
H99 | 0.1659 | 0.4559 | 0.0196 | 0.054* | |
C36 | 0.81986 (19) | 0.79670 (14) | 0.21606 (14) | 0.0346 (5) | |
H36 | 0.8053 | 0.8413 | 0.1839 | 0.041* | |
C16 | 0.7360 (2) | 0.25162 (16) | 0.34500 (15) | 0.0421 (6) | |
H16A | 0.7461 | 0.2392 | 0.3964 | 0.063* | |
H16B | 0.7764 | 0.2145 | 0.325 | 0.063* | |
H16C | 0.6638 | 0.2459 | 0.3182 | 0.063* | |
C97 | 0.22047 (18) | 0.36545 (17) | 0.09280 (14) | 0.0391 (6) | |
H97 | 0.1568 | 0.3403 | 0.088 | 0.047* | |
C5 | 0.6493 (2) | 0.45047 (18) | 0.46948 (13) | 0.0403 (6) | |
H5 | 0.6541 | 0.4496 | 0.5198 | 0.048* | |
C84 | 0.62703 (16) | 0.30447 (14) | 0.05037 (12) | 0.0272 (5) | |
H84A | 0.5975 | 0.3556 | 0.0291 | 0.041* | |
H84B | 0.5747 | 0.2722 | 0.0627 | 0.041* | |
H84C | 0.653 | 0.2753 | 0.0152 | 0.041* | |
C22 | 0.5128 (2) | 0.65250 (17) | 0.32183 (18) | 0.0479 (7) | |
H22A | 0.5021 | 0.6571 | 0.3699 | 0.072* | |
H22B | 0.4648 | 0.6877 | 0.2875 | 0.072* | |
H22C | 0.5826 | 0.6684 | 0.3249 | 0.072* | |
C34 | 0.90967 (19) | 0.79704 (15) | 0.27453 (15) | 0.0381 (6) | |
H34 | 0.9551 | 0.8412 | 0.2812 | 0.046* | |
C51 | 0.6690 (3) | 0.7481 (3) | 0.06604 (17) | 0.0856 (14) | |
H51A | 0.6991 | 0.8014 | 0.0655 | 0.128* | |
H51B | 0.6043 | 0.7449 | 0.0274 | 0.128* | |
H51C | 0.7158 | 0.707 | 0.058 | 0.128* | |
C70 | 0.9590 (3) | 0.63750 (17) | 0.14556 (18) | 0.0594 (9) | |
H70A | 0.9968 | 0.636 | 0.1095 | 0.089* | |
H70B | 0.9829 | 0.6828 | 0.1787 | 0.089* | |
H70C | 0.8862 | 0.6439 | 0.1208 | 0.089* | |
C12 | 0.8865 (2) | 0.3484 (2) | 0.3748 (2) | 0.0659 (10) | |
H12A | 0.9079 | 0.4031 | 0.3671 | 0.099* | |
H12B | 0.9237 | 0.3098 | 0.3536 | 0.099* | |
H12C | 0.9012 | 0.3382 | 0.427 | 0.099* | |
C41 | 0.8358 (2) | 0.6140 (2) | 0.43148 (15) | 0.0503 (7) | |
H41A | 0.8668 | 0.6621 | 0.4584 | 0.075* | |
H41B | 0.8456 | 0.5683 | 0.4649 | 0.075* | |
H41C | 0.7628 | 0.6232 | 0.4094 | 0.075* | |
C55 | 0.5746 (3) | 0.7973 (3) | 0.1534 (2) | 0.0811 (13) | |
H55A | 0.5537 | 0.7816 | 0.196 | 0.122* | |
H55B | 0.5145 | 0.8003 | 0.1107 | 0.122* | |
H55C | 0.6079 | 0.8499 | 0.1619 | 0.122* | |
C45 | 1.0018 (2) | 0.5779 (2) | 0.40557 (15) | 0.0496 (7) | |
H45A | 1.0338 | 0.5688 | 0.3668 | 0.074* | |
H45B | 1.0098 | 0.5298 | 0.4362 | 0.074* | |
H45C | 1.0344 | 0.6237 | 0.4353 | 0.074* | |
C74 | 1.0914 (2) | 0.5443 (2) | 0.2283 (2) | 0.0683 (11) | |
H74A | 1.0998 | 0.4952 | 0.2575 | 0.103* | |
H74B | 1.1186 | 0.5901 | 0.26 | 0.103* | |
H74C | 1.1283 | 0.5389 | 0.1919 | 0.103* | |
H103 | 0.470 (2) | 0.4615 (19) | 0.1073 (16) | 0.051 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S92 | 0.0203 (2) | 0.0228 (3) | 0.0183 (2) | −0.0030 (2) | 0.00325 (18) | 0.00112 (19) |
Si91 | 0.0132 (2) | 0.0169 (3) | 0.0175 (2) | −0.0017 (2) | 0.00519 (19) | −0.0012 (2) |
O90 | 0.0164 (6) | 0.0215 (7) | 0.0171 (6) | −0.0019 (5) | 0.0066 (5) | −0.0001 (5) |
O88 | 0.0163 (7) | 0.0190 (7) | 0.0228 (7) | −0.0012 (5) | 0.0044 (5) | −0.0040 (6) |
O89 | 0.0146 (6) | 0.0221 (7) | 0.0185 (6) | −0.0006 (5) | 0.0068 (5) | −0.0019 (5) |
C60 | 0.0150 (9) | 0.0210 (10) | 0.0233 (9) | 0.0026 (8) | 0.0061 (7) | 0.0052 (8) |
N103 | 0.0275 (10) | 0.0316 (11) | 0.0321 (10) | −0.0047 (8) | 0.0144 (8) | 0.0000 (8) |
C65 | 0.0258 (10) | 0.0246 (11) | 0.0173 (9) | 0.0025 (8) | 0.0070 (8) | −0.0012 (8) |
C59 | 0.0157 (9) | 0.0186 (10) | 0.0163 (8) | 0.0033 (7) | 0.0064 (7) | 0.0038 (7) |
C67 | 0.0180 (9) | 0.0193 (10) | 0.0179 (9) | 0.0011 (8) | 0.0048 (7) | 0.0020 (7) |
C9 | 0.0218 (10) | 0.0287 (12) | 0.0305 (11) | 0.0004 (8) | 0.0142 (8) | 0.0001 (9) |
C31 | 0.0204 (10) | 0.0261 (12) | 0.0299 (11) | 0.0018 (8) | 0.0043 (8) | −0.0106 (9) |
C95 | 0.0322 (12) | 0.0297 (13) | 0.0522 (15) | −0.0023 (10) | 0.0154 (11) | 0.0139 (11) |
C63 | 0.0282 (11) | 0.0340 (12) | 0.0207 (10) | 0.0056 (9) | 0.0133 (8) | 0.0034 (9) |
C2 | 0.0223 (10) | 0.0276 (11) | 0.0227 (10) | 0.0007 (9) | 0.0088 (8) | 0.0033 (8) |
C101 | 0.0430 (14) | 0.0425 (15) | 0.0335 (12) | 0.0109 (11) | 0.0232 (11) | 0.0150 (11) |
C1 | 0.0176 (9) | 0.0246 (11) | 0.0187 (9) | −0.0035 (8) | 0.0081 (7) | −0.0004 (8) |
C80 | 0.0322 (12) | 0.0217 (11) | 0.0337 (11) | −0.0017 (9) | 0.0137 (9) | 0.0026 (9) |
C78 | 0.0216 (10) | 0.0208 (10) | 0.0216 (9) | −0.0027 (8) | 0.0077 (8) | −0.0017 (8) |
C68 | 0.0233 (10) | 0.0226 (11) | 0.0385 (12) | −0.0036 (8) | 0.0155 (9) | −0.0022 (9) |
C10 | 0.0277 (11) | 0.0289 (12) | 0.0262 (10) | 0.0079 (9) | 0.0102 (9) | 0.0064 (9) |
C61 | 0.0191 (10) | 0.0312 (12) | 0.0246 (10) | 0.0007 (8) | 0.0112 (8) | 0.0071 (9) |
C7 | 0.0379 (13) | 0.0465 (15) | 0.0349 (12) | 0.0045 (11) | 0.0239 (10) | −0.0042 (11) |
C3 | 0.0342 (12) | 0.0421 (14) | 0.0229 (11) | 0.0023 (10) | 0.0078 (9) | 0.0071 (10) |
C32 | 0.0201 (11) | 0.0303 (13) | 0.0452 (13) | −0.0021 (9) | 0.0038 (10) | −0.0152 (11) |
C93 | 0.0242 (11) | 0.0388 (14) | 0.0399 (13) | 0.0014 (10) | 0.0044 (10) | 0.0101 (11) |
C38 | 0.0266 (11) | 0.0194 (11) | 0.0326 (11) | −0.0004 (8) | 0.0091 (9) | −0.0054 (9) |
C30 | 0.0171 (9) | 0.0202 (10) | 0.0272 (10) | −0.0003 (8) | 0.0076 (8) | −0.0069 (8) |
C29 | 0.0245 (11) | 0.0373 (14) | 0.0511 (14) | 0.0012 (10) | 0.0106 (10) | −0.0037 (11) |
C49 | 0.0375 (13) | 0.0217 (11) | 0.0309 (11) | −0.0011 (9) | 0.0016 (9) | 0.0003 (9) |
C20 | 0.0245 (11) | 0.0305 (12) | 0.0403 (12) | 0.0068 (9) | 0.0161 (9) | 0.0006 (10) |
C39 | 0.0269 (12) | 0.0315 (13) | 0.0341 (12) | 0.0004 (10) | −0.0060 (9) | −0.0038 (10) |
C99 | 0.0271 (12) | 0.074 (2) | 0.0351 (13) | 0.0169 (12) | 0.0116 (10) | 0.0199 (13) |
C36 | 0.0406 (13) | 0.0203 (12) | 0.0440 (13) | −0.0029 (10) | 0.0140 (11) | −0.0021 (10) |
C16 | 0.0518 (16) | 0.0361 (14) | 0.0411 (14) | −0.0012 (12) | 0.0178 (12) | 0.0005 (11) |
C97 | 0.0215 (11) | 0.0511 (16) | 0.0462 (14) | −0.0039 (11) | 0.0122 (10) | 0.0015 (12) |
C5 | 0.0456 (15) | 0.0583 (18) | 0.0211 (11) | −0.0003 (12) | 0.0161 (10) | −0.0003 (11) |
C84 | 0.0240 (11) | 0.0268 (12) | 0.0290 (11) | −0.0058 (9) | 0.0049 (9) | −0.0048 (9) |
C22 | 0.0302 (13) | 0.0333 (15) | 0.077 (2) | 0.0046 (11) | 0.0111 (13) | −0.0021 (13) |
C34 | 0.0328 (12) | 0.0277 (13) | 0.0565 (15) | −0.0115 (10) | 0.0173 (11) | −0.0150 (11) |
C51 | 0.052 (2) | 0.160 (4) | 0.0393 (17) | 0.002 (2) | 0.0048 (14) | 0.023 (2) |
C70 | 0.113 (3) | 0.0236 (14) | 0.0606 (18) | −0.0038 (15) | 0.0550 (19) | −0.0018 (13) |
C12 | 0.0281 (14) | 0.0489 (19) | 0.118 (3) | 0.0043 (13) | 0.0173 (16) | −0.0282 (19) |
C41 | 0.0365 (14) | 0.068 (2) | 0.0446 (15) | 0.0017 (13) | 0.0088 (12) | 0.0127 (14) |
C55 | 0.0396 (17) | 0.117 (3) | 0.069 (2) | 0.0280 (19) | −0.0128 (16) | −0.029 (2) |
C45 | 0.0371 (15) | 0.0613 (19) | 0.0412 (14) | 0.0154 (13) | −0.0029 (11) | 0.0023 (13) |
C74 | 0.0250 (13) | 0.064 (2) | 0.106 (3) | −0.0087 (13) | 0.0031 (15) | −0.051 (2) |
Geometric parameters (Å, º) top
S92—Si91 | 2.0286 (7) | C93—H93 | 0.93 |
Si91—O88 | 1.6502 (14) | C38—C36 | 1.399 (3) |
Si91—O90 | 1.6561 (14) | C38—C30 | 1.400 (3) |
Si91—O89 | 1.6580 (14) | C38—C49 | 1.526 (3) |
O90—C1 | 1.395 (2) | C29—C20 | 1.526 (3) |
O88—C30 | 1.383 (2) | C29—H29A | 0.96 |
O89—C59 | 1.382 (2) | C29—H29B | 0.96 |
C60—C61 | 1.393 (3) | C29—H29C | 0.96 |
C60—C59 | 1.405 (3) | C49—C51 | 1.498 (4) |
C60—C68 | 1.512 (3) | C49—C55 | 1.523 (4) |
N103—C101 | 1.323 (3) | C49—H49 | 0.98 |
N103—C93 | 1.331 (3) | C20—C22 | 1.520 (4) |
N103—H103 | 0.93 (3) | C20—H20 | 0.98 |
C65—C63 | 1.384 (3) | C39—C41 | 1.513 (4) |
C65—C67 | 1.393 (3) | C39—C45 | 1.524 (3) |
C65—H65 | 0.93 | C39—H39 | 0.98 |
C59—C67 | 1.411 (3) | C99—C97 | 1.370 (4) |
C67—C78 | 1.520 (3) | C99—H99 | 0.93 |
C9—C1 | 1.397 (3) | C36—C34 | 1.378 (4) |
C9—C7 | 1.399 (3) | C36—H36 | 0.93 |
C9—C20 | 1.518 (3) | C16—H16A | 0.96 |
C31—C32 | 1.395 (3) | C16—H16B | 0.96 |
C31—C30 | 1.410 (3) | C16—H16C | 0.96 |
C31—C39 | 1.514 (3) | C97—H97 | 0.93 |
C95—C93 | 1.370 (3) | C5—H5 | 0.93 |
C95—C97 | 1.373 (3) | C84—H84A | 0.96 |
C95—H95 | 0.93 | C84—H84B | 0.96 |
C63—C61 | 1.382 (3) | C84—H84C | 0.96 |
C63—H63 | 0.93 | C22—H22A | 0.96 |
C2—C3 | 1.394 (3) | C22—H22B | 0.96 |
C2—C1 | 1.404 (3) | C22—H22C | 0.96 |
C2—C10 | 1.518 (3) | C34—H34 | 0.93 |
C101—C99 | 1.374 (4) | C51—H51A | 0.96 |
C101—H101 | 0.93 | C51—H51B | 0.96 |
C80—C78 | 1.535 (3) | C51—H51C | 0.96 |
C80—H80A | 0.96 | C70—H70A | 0.96 |
C80—H80B | 0.96 | C70—H70B | 0.96 |
C80—H80C | 0.96 | C70—H70C | 0.96 |
C78—C84 | 1.531 (3) | C12—H12A | 0.96 |
C78—H78 | 0.98 | C12—H12B | 0.96 |
C68—C70 | 1.515 (3) | C12—H12C | 0.96 |
C68—C74 | 1.522 (3) | C41—H41A | 0.96 |
C68—H68 | 0.98 | C41—H41B | 0.96 |
C10—C12 | 1.518 (3) | C41—H41C | 0.96 |
C10—C16 | 1.524 (3) | C55—H55A | 0.96 |
C10—H10 | 0.98 | C55—H55B | 0.96 |
C61—H61 | 0.93 | C55—H55C | 0.96 |
C7—C5 | 1.385 (4) | C45—H45A | 0.96 |
C7—H7 | 0.93 | C45—H45B | 0.96 |
C3—C5 | 1.376 (4) | C45—H45C | 0.96 |
C3—H3 | 0.93 | C74—H74A | 0.96 |
C32—C34 | 1.379 (4) | C74—H74B | 0.96 |
C32—H32 | 0.93 | C74—H74C | 0.96 |
| | | |
O88—Si91—O90 | 102.16 (7) | H29B—C29—H29C | 109.5 |
O88—Si91—O89 | 106.70 (7) | C51—C49—C55 | 110.7 (3) |
O90—Si91—O89 | 105.69 (7) | C51—C49—C38 | 113.1 (2) |
O88—Si91—S92 | 116.74 (6) | C55—C49—C38 | 111.4 (2) |
O90—Si91—S92 | 111.12 (5) | C51—C49—H49 | 107.1 |
O89—Si91—S92 | 113.32 (5) | C55—C49—H49 | 107.1 |
C1—O90—Si91 | 130.13 (12) | C38—C49—H49 | 107.1 |
C30—O88—Si91 | 135.01 (13) | C9—C20—C22 | 111.3 (2) |
C59—O89—Si91 | 129.35 (11) | C9—C20—C29 | 111.6 (2) |
C61—C60—C59 | 118.10 (19) | C22—C20—C29 | 111.0 (2) |
C61—C60—C68 | 120.07 (18) | C9—C20—H20 | 107.6 |
C59—C60—C68 | 121.83 (18) | C22—C20—H20 | 107.6 |
C101—N103—C93 | 122.3 (2) | C29—C20—H20 | 107.6 |
C101—N103—H103 | 118.3 (18) | C41—C39—C31 | 110.4 (2) |
C93—N103—H103 | 119.4 (18) | C41—C39—C45 | 110.2 (2) |
C63—C65—C67 | 122.1 (2) | C31—C39—C45 | 113.6 (2) |
C63—C65—H65 | 118.9 | C41—C39—H39 | 107.5 |
C67—C65—H65 | 118.9 | C31—C39—H39 | 107.5 |
O89—C59—C60 | 117.59 (17) | C45—C39—H39 | 107.5 |
O89—C59—C67 | 120.98 (17) | C97—C99—C101 | 119.5 (2) |
C60—C59—C67 | 121.35 (17) | C97—C99—H99 | 120.2 |
C65—C67—C59 | 117.55 (18) | C101—C99—H99 | 120.2 |
C65—C67—C78 | 118.83 (18) | C34—C36—C38 | 121.6 (2) |
C59—C67—C78 | 123.43 (17) | C34—C36—H36 | 119.2 |
C1—C9—C7 | 117.3 (2) | C38—C36—H36 | 119.2 |
C1—C9—C20 | 122.39 (19) | C10—C16—H16A | 109.5 |
C7—C9—C20 | 120.3 (2) | C10—C16—H16B | 109.5 |
C32—C31—C30 | 117.4 (2) | H16A—C16—H16B | 109.5 |
C32—C31—C39 | 121.22 (19) | C10—C16—H16C | 109.5 |
C30—C31—C39 | 121.3 (2) | H16A—C16—H16C | 109.5 |
C93—C95—C97 | 119.0 (2) | H16B—C16—H16C | 109.5 |
C93—C95—H95 | 120.5 | C99—C97—C95 | 119.6 (2) |
C97—C95—H95 | 120.5 | C99—C97—H97 | 120.2 |
C61—C63—C65 | 119.03 (19) | C95—C97—H97 | 120.2 |
C61—C63—H63 | 120.5 | C3—C5—C7 | 119.5 (2) |
C65—C63—H63 | 120.5 | C3—C5—H5 | 120.3 |
C3—C2—C1 | 117.4 (2) | C7—C5—H5 | 120.3 |
C3—C2—C10 | 120.36 (19) | C78—C84—H84A | 109.5 |
C1—C2—C10 | 122.16 (18) | C78—C84—H84B | 109.5 |
N103—C101—C99 | 119.5 (2) | H84A—C84—H84B | 109.5 |
N103—C101—H101 | 120.2 | C78—C84—H84C | 109.5 |
C99—C101—H101 | 120.2 | H84A—C84—H84C | 109.5 |
O90—C1—C9 | 118.59 (17) | H84B—C84—H84C | 109.5 |
O90—C1—C2 | 118.88 (18) | C20—C22—H22A | 109.5 |
C9—C1—C2 | 122.41 (18) | C20—C22—H22B | 109.5 |
C78—C80—H80A | 109.5 | H22A—C22—H22B | 109.5 |
C78—C80—H80B | 109.5 | C20—C22—H22C | 109.5 |
H80A—C80—H80B | 109.5 | H22A—C22—H22C | 109.5 |
C78—C80—H80C | 109.5 | H22B—C22—H22C | 109.5 |
H80A—C80—H80C | 109.5 | C36—C34—C32 | 119.9 (2) |
H80B—C80—H80C | 109.5 | C36—C34—H34 | 120.1 |
C67—C78—C84 | 113.03 (17) | C32—C34—H34 | 120.1 |
C67—C78—C80 | 109.19 (16) | C49—C51—H51A | 109.5 |
C84—C78—C80 | 110.44 (17) | C49—C51—H51B | 109.5 |
C67—C78—H78 | 108 | H51A—C51—H51B | 109.5 |
C84—C78—H78 | 108 | C49—C51—H51C | 109.5 |
C80—C78—H78 | 108 | H51A—C51—H51C | 109.5 |
C60—C68—C70 | 111.4 (2) | H51B—C51—H51C | 109.5 |
C60—C68—C74 | 111.50 (19) | C68—C70—H70A | 109.5 |
C70—C68—C74 | 111.4 (3) | C68—C70—H70B | 109.5 |
C60—C68—H68 | 107.4 | H70A—C70—H70B | 109.5 |
C70—C68—H68 | 107.4 | C68—C70—H70C | 109.5 |
C74—C68—H68 | 107.4 | H70A—C70—H70C | 109.5 |
C2—C10—C12 | 112.6 (2) | H70B—C70—H70C | 109.5 |
C2—C10—C16 | 110.95 (19) | C10—C12—H12A | 109.5 |
C12—C10—C16 | 110.4 (2) | C10—C12—H12B | 109.5 |
C2—C10—H10 | 107.5 | H12A—C12—H12B | 109.5 |
C12—C10—H10 | 107.5 | C10—C12—H12C | 109.5 |
C16—C10—H10 | 107.5 | H12A—C12—H12C | 109.5 |
C63—C61—C60 | 121.77 (19) | H12B—C12—H12C | 109.5 |
C63—C61—H61 | 119.1 | C39—C41—H41A | 109.5 |
C60—C61—H61 | 119.1 | C39—C41—H41B | 109.5 |
C5—C7—C9 | 121.6 (2) | H41A—C41—H41B | 109.5 |
C5—C7—H7 | 119.2 | C39—C41—H41C | 109.5 |
C9—C7—H7 | 119.2 | H41A—C41—H41C | 109.5 |
C5—C3—C2 | 121.8 (2) | H41B—C41—H41C | 109.5 |
C5—C3—H3 | 119.1 | C49—C55—H55A | 109.5 |
C2—C3—H3 | 119.1 | C49—C55—H55B | 109.5 |
C34—C32—C31 | 121.5 (2) | H55A—C55—H55B | 109.5 |
C34—C32—H32 | 119.2 | C49—C55—H55C | 109.5 |
C31—C32—H32 | 119.2 | H55A—C55—H55C | 109.5 |
N103—C93—C95 | 120.1 (2) | H55B—C55—H55C | 109.5 |
N103—C93—H93 | 120 | C39—C45—H45A | 109.5 |
C95—C93—H93 | 120 | C39—C45—H45B | 109.5 |
C36—C38—C30 | 117.4 (2) | H45A—C45—H45B | 109.5 |
C36—C38—C49 | 120.0 (2) | C39—C45—H45C | 109.5 |
C30—C38—C49 | 122.62 (19) | H45A—C45—H45C | 109.5 |
O88—C30—C38 | 120.94 (17) | H45B—C45—H45C | 109.5 |
O88—C30—C31 | 116.78 (19) | C68—C74—H74A | 109.5 |
C38—C30—C31 | 122.1 (2) | C68—C74—H74B | 109.5 |
C20—C29—H29A | 109.5 | H74A—C74—H74B | 109.5 |
C20—C29—H29B | 109.5 | C68—C74—H74C | 109.5 |
H29A—C29—H29B | 109.5 | H74A—C74—H74C | 109.5 |
C20—C29—H29C | 109.5 | H74B—C74—H74C | 109.5 |
H29A—C29—H29C | 109.5 | | |
| | | |
O88—Si91—O90—C1 | −26.66 (17) | C1—C2—C10—C16 | −112.8 (2) |
O89—Si91—O90—C1 | 84.80 (17) | C65—C63—C61—C60 | −1.6 (3) |
S92—Si91—O90—C1 | −151.87 (14) | C59—C60—C61—C63 | −0.1 (3) |
O90—Si91—O88—C30 | 159.39 (17) | C68—C60—C61—C63 | 179.31 (19) |
O89—Si91—O88—C30 | 48.68 (19) | C1—C9—C7—C5 | 0.3 (4) |
S92—Si91—O88—C30 | −79.20 (18) | C20—C9—C7—C5 | 179.4 (2) |
O88—Si91—O89—C59 | −129.18 (16) | C1—C2—C3—C5 | 0.8 (4) |
O90—Si91—O89—C59 | 122.60 (16) | C10—C2—C3—C5 | −176.2 (2) |
S92—Si91—O89—C59 | 0.68 (17) | C30—C31—C32—C34 | 1.8 (3) |
Si91—O89—C59—C60 | 113.98 (17) | C39—C31—C32—C34 | −175.7 (2) |
Si91—O89—C59—C67 | −69.4 (2) | C101—N103—C93—C95 | −0.3 (4) |
C61—C60—C59—O89 | 179.24 (16) | C97—C95—C93—N103 | 1.5 (4) |
C68—C60—C59—O89 | −0.2 (3) | Si91—O88—C30—C38 | 83.3 (2) |
C61—C60—C59—C67 | 2.6 (3) | Si91—O88—C30—C31 | −101.0 (2) |
C68—C60—C59—C67 | −176.80 (18) | C36—C38—C30—O88 | 177.51 (19) |
C63—C65—C67—C59 | 1.5 (3) | C49—C38—C30—O88 | −1.3 (3) |
C63—C65—C67—C78 | −173.67 (18) | C36—C38—C30—C31 | 2.0 (3) |
O89—C59—C67—C65 | −179.79 (17) | C49—C38—C30—C31 | −176.8 (2) |
C60—C59—C67—C65 | −3.3 (3) | C32—C31—C30—O88 | −178.35 (18) |
O89—C59—C67—C78 | −4.8 (3) | C39—C31—C30—O88 | −0.9 (3) |
C60—C59—C67—C78 | 171.67 (18) | C32—C31—C30—C38 | −2.7 (3) |
C67—C65—C63—C61 | 0.9 (3) | C39—C31—C30—C38 | 174.7 (2) |
C93—N103—C101—C99 | −0.8 (4) | C36—C38—C49—C51 | 55.7 (3) |
Si91—O90—C1—C9 | 87.2 (2) | C30—C38—C49—C51 | −125.4 (3) |
Si91—O90—C1—C2 | −96.8 (2) | C36—C38—C49—C55 | −69.7 (3) |
C7—C9—C1—O90 | 177.37 (19) | C30—C38—C49—C55 | 109.1 (3) |
C20—C9—C1—O90 | −1.8 (3) | C1—C9—C20—C22 | −123.6 (2) |
C7—C9—C1—C2 | 1.5 (3) | C7—C9—C20—C22 | 57.3 (3) |
C20—C9—C1—C2 | −177.7 (2) | C1—C9—C20—C29 | 111.9 (2) |
C3—C2—C1—O90 | −177.87 (19) | C7—C9—C20—C29 | −67.2 (3) |
C10—C2—C1—O90 | −1.0 (3) | C32—C31—C39—C41 | 89.8 (3) |
C3—C2—C1—C9 | −2.0 (3) | C30—C31—C39—C41 | −87.5 (3) |
C10—C2—C1—C9 | 174.9 (2) | C32—C31—C39—C45 | −34.5 (3) |
C65—C67—C78—C84 | −54.7 (2) | C30—C31—C39—C45 | 148.2 (2) |
C59—C67—C78—C84 | 130.4 (2) | N103—C101—C99—C97 | 0.6 (4) |
C65—C67—C78—C80 | 68.6 (2) | C30—C38—C36—C34 | −0.4 (4) |
C59—C67—C78—C80 | −106.3 (2) | C49—C38—C36—C34 | 178.5 (2) |
C61—C60—C68—C70 | 69.9 (3) | C101—C99—C97—C95 | 0.6 (4) |
C59—C60—C68—C70 | −110.7 (2) | C93—C95—C97—C99 | −1.6 (4) |
C61—C60—C68—C74 | −55.2 (3) | C2—C3—C5—C7 | 0.9 (4) |
C59—C60—C68—C74 | 124.2 (3) | C9—C7—C5—C3 | −1.4 (4) |
C3—C2—C10—C12 | −60.3 (3) | C38—C36—C34—C32 | −0.5 (4) |
C1—C2—C10—C12 | 122.9 (3) | C31—C32—C34—C36 | −0.2 (4) |
C3—C2—C10—C16 | 64.0 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N103—H103···S92 | 0.93 (3) | 2.11 (3) | 3.024 (2) | 167 (3) |
Crystal data top
C36H51O3SSi·C5H6N | F(000) = 1456 |
Mr = 672.02 | Dx = 1.126 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 17688 reflections |
a = 13.4625 (6) Å | θ = 3.4–29.4° |
b = 16.3181 (5) Å | µ = 0.15 mm−1 |
c = 18.8624 (8) Å | T = 150 K |
β = 106.983 (3)° | Plate, colorless |
V = 3963.0 (3) Å3 | 0.38 × 0.31 × 0.15 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 5331 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.049 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.1° |
rotation method scans | h = −16→13 |
22240 measured reflections | k = −19→20 |
7758 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H 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 reflections | Δρmax = 0.50 e Å−3 |
440 parameters | Δρmin = −0.33 e Å−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 | x | y | z | Uiso*/Ueq | |
S92 | 0.59552 (4) | 0.52625 (3) | 0.09033 (3) | 0.02977 (13) | |
Si91 | 0.68597 (4) | 0.51559 (3) | 0.19646 (3) | 0.02237 (13) | |
O90 | 0.63001 (10) | 0.45687 (9) | 0.24520 (7) | 0.0255 (3) | |
O88 | 0.70918 (10) | 0.60024 (9) | 0.24582 (7) | 0.0276 (3) | |
O89 | 0.80002 (10) | 0.47280 (9) | 0.20390 (7) | 0.0254 (3) | |
C60 | 0.92779 (15) | 0.48645 (13) | 0.14028 (11) | 0.0277 (4) | |
N103 | 0.40577 (16) | 0.43769 (14) | 0.10528 (11) | 0.0405 (5) | |
C65 | 0.84637 (17) | 0.35141 (14) | 0.05295 (11) | 0.0322 (5) | |
H65 | 0.8197 | 0.3063 | 0.0235 | 0.039* | |
C59 | 0.84112 (15) | 0.44543 (12) | 0.14920 (10) | 0.0239 (4) | |
C67 | 0.80049 (15) | 0.37562 (13) | 0.10711 (10) | 0.0256 (4) | |
C9 | 0.57326 (18) | 0.50879 (15) | 0.34581 (13) | 0.0375 (5) | |
C31 | 0.86574 (17) | 0.66576 (15) | 0.31464 (13) | 0.0372 (5) | |
C95 | 0.3108 (2) | 0.33654 (18) | 0.14292 (17) | 0.0545 (7) | |
H95 | 0.3082 | 0.2915 | 0.1726 | 0.065* | |
C63 | 0.93018 (17) | 0.39253 (15) | 0.04191 (12) | 0.0359 (5) | |
H63 | 0.9591 | 0.3756 | 0.0052 | 0.043* | |
C2 | 0.70701 (18) | 0.40186 (15) | 0.36717 (12) | 0.0345 (5) | |
C101 | 0.3216 (2) | 0.46920 (19) | 0.05956 (14) | 0.0511 (7) | |
H101 | 0.326 | 0.5153 | 0.0316 | 0.061* | |
C1 | 0.63841 (16) | 0.45715 (13) | 0.32060 (11) | 0.0282 (4) | |
C80 | 0.7644 (2) | 0.24126 (15) | 0.15647 (14) | 0.0415 (6) | |
H80A | 0.7897 | 0.2109 | 0.1217 | 0.062* | |
H80B | 0.7125 | 0.2096 | 0.1699 | 0.062* | |
H80C | 0.8208 | 0.2527 | 0.2 | 0.062* | |
C78 | 0.71648 (16) | 0.32215 (13) | 0.12097 (11) | 0.0288 (4) | |
H78 | 0.6881 | 0.3506 | 0.1565 | 0.035* | |
C68 | 0.97582 (17) | 0.55880 (14) | 0.18862 (13) | 0.0361 (5) | |
H68 | 0.9395 | 0.5649 | 0.2264 | 0.043* | |
C10 | 0.77064 (19) | 0.34151 (15) | 0.33829 (13) | 0.0399 (6) | |
H10 | 0.7578 | 0.3526 | 0.2853 | 0.048* | |
C61 | 0.97049 (17) | 0.45896 (14) | 0.08605 (12) | 0.0336 (5) | |
H61 | 1.0278 | 0.4861 | 0.0793 | 0.04* | |
C7 | 0.5812 (2) | 0.50460 (19) | 0.42156 (15) | 0.0536 (7) | |
H7 | 0.5387 | 0.5378 | 0.4402 | 0.064* | |
C3 | 0.7113 (2) | 0.40198 (18) | 0.44186 (13) | 0.0481 (6) | |
H3 | 0.7569 | 0.3665 | 0.4742 | 0.058* | |
C32 | 0.93214 (19) | 0.73219 (16) | 0.32308 (15) | 0.0467 (6) | |
H32 | 0.9924 | 0.7331 | 0.3628 | 0.056* | |
C93 | 0.40329 (19) | 0.37290 (17) | 0.14667 (15) | 0.0494 (7) | |
H93 | 0.4646 | 0.3521 | 0.1783 | 0.059* | |
C38 | 0.75226 (18) | 0.73130 (14) | 0.20325 (13) | 0.0361 (5) | |
C30 | 0.77624 (16) | 0.66583 (13) | 0.25280 (12) | 0.0291 (5) | |
C29 | 0.3847 (2) | 0.53915 (19) | 0.28675 (18) | 0.0573 (7) | |
H29A | 0.3747 | 0.484 | 0.2683 | 0.086* | |
H29B | 0.3376 | 0.575 | 0.2526 | 0.086* | |
H29C | 0.3718 | 0.5417 | 0.3341 | 0.086* | |
C49 | 0.6529 (2) | 0.73420 (16) | 0.13837 (14) | 0.0461 (6) | |
H49 | 0.6204 | 0.68 | 0.1346 | 0.055* | |
C20 | 0.49605 (18) | 0.56564 (16) | 0.29500 (15) | 0.0427 (6) | |
H20 | 0.5069 | 0.5624 | 0.2459 | 0.051* | |
C39 | 0.8858 (2) | 0.59767 (17) | 0.37126 (14) | 0.0473 (7) | |
H39 | 0.852 | 0.5481 | 0.3461 | 0.057* | |
C99 | 0.2270 (2) | 0.4338 (2) | 0.05317 (15) | 0.0610 (8) | |
H99 | 0.167 | 0.4553 | 0.0205 | 0.073* | |
C36 | 0.8219 (2) | 0.79648 (16) | 0.21534 (16) | 0.0485 (6) | |
H36 | 0.8078 | 0.8408 | 0.1829 | 0.058* | |
C16 | 0.7356 (3) | 0.25384 (19) | 0.34557 (18) | 0.0634 (8) | |
H16A | 0.7489 | 0.2405 | 0.3971 | 0.095* | |
H16B | 0.7733 | 0.2169 | 0.3233 | 0.095* | |
H16C | 0.6626 | 0.249 | 0.3209 | 0.095* | |
C97 | 0.2216 (2) | 0.3671 (2) | 0.09497 (16) | 0.0550 (7) | |
H97 | 0.1579 | 0.3425 | 0.091 | 0.066* | |
C5 | 0.6502 (2) | 0.4527 (2) | 0.46907 (14) | 0.0583 (8) | |
H5 | 0.6553 | 0.4522 | 0.5193 | 0.07* | |
C84 | 0.62666 (18) | 0.30549 (16) | 0.05096 (13) | 0.0404 (6) | |
H84A | 0.5981 | 0.3566 | 0.029 | 0.061* | |
H84B | 0.5738 | 0.2744 | 0.0638 | 0.061* | |
H84C | 0.6518 | 0.275 | 0.0162 | 0.061* | |
C22 | 0.5137 (2) | 0.65376 (19) | 0.3207 (2) | 0.0683 (9) | |
H22A | 0.5049 | 0.6587 | 0.3692 | 0.102* | |
H22B | 0.4644 | 0.6884 | 0.2868 | 0.102* | |
H22C | 0.5829 | 0.67 | 0.3224 | 0.102* | |
C34 | 0.9113 (2) | 0.79689 (17) | 0.27425 (17) | 0.0525 (7) | |
H34 | 0.9572 | 0.8407 | 0.2809 | 0.063* | |
C51 | 0.6724 (3) | 0.7514 (4) | 0.0657 (2) | 0.1177 (19) | |
H51A | 0.702 | 0.8051 | 0.0669 | 0.177* | |
H51B | 0.608 | 0.7489 | 0.0267 | 0.177* | |
H51C | 0.7196 | 0.7113 | 0.0569 | 0.177* | |
C70 | 0.9606 (4) | 0.63716 (19) | 0.1445 (2) | 0.0829 (12) | |
H70A | 1.0001 | 0.6349 | 0.1095 | 0.124* | |
H70B | 0.9838 | 0.6827 | 0.1774 | 0.124* | |
H70C | 0.8883 | 0.6438 | 0.1184 | 0.124* | |
C12 | 0.8856 (2) | 0.3496 (2) | 0.3744 (3) | 0.0913 (14) | |
H12A | 0.9072 | 0.4044 | 0.3679 | 0.137* | |
H12B | 0.9219 | 0.3116 | 0.3521 | 0.137* | |
H12C | 0.9011 | 0.3378 | 0.4264 | 0.137* | |
C41 | 0.8371 (3) | 0.6176 (3) | 0.43166 (19) | 0.0745 (10) | |
H41A | 0.8681 | 0.6664 | 0.457 | 0.112* | |
H41B | 0.8482 | 0.5729 | 0.4662 | 0.112* | |
H41C | 0.7639 | 0.6262 | 0.4102 | 0.112* | |
C55 | 0.5761 (3) | 0.7956 (3) | 0.1521 (2) | 0.1112 (18) | |
H55A | 0.5604 | 0.7818 | 0.1971 | 0.167* | |
H55B | 0.5134 | 0.7944 | 0.1114 | 0.167* | |
H55C | 0.6057 | 0.8495 | 0.1564 | 0.167* | |
C45 | 1.0006 (2) | 0.5784 (2) | 0.40479 (17) | 0.0710 (10) | |
H45A | 1.0319 | 0.5691 | 0.3658 | 0.106* | |
H45B | 1.0081 | 0.5302 | 0.4351 | 0.106* | |
H45C | 1.0344 | 0.6237 | 0.4346 | 0.106* | |
C74 | 1.0892 (2) | 0.5439 (3) | 0.2286 (3) | 0.0959 (15) | |
H74A | 1.096 | 0.4949 | 0.2578 | 0.144* | |
H74B | 1.1166 | 0.5896 | 0.2603 | 0.144* | |
H74C | 1.127 | 0.5376 | 0.1929 | 0.144* | |
H103 | 0.465 (2) | 0.4623 (18) | 0.1052 (15) | 0.053 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S92 | 0.0284 (3) | 0.0330 (3) | 0.0259 (2) | −0.0044 (2) | 0.00491 (19) | 0.0017 (2) |
Si91 | 0.0194 (3) | 0.0245 (3) | 0.0238 (2) | −0.0016 (2) | 0.0073 (2) | −0.0013 (2) |
O90 | 0.0238 (7) | 0.0295 (8) | 0.0245 (6) | −0.0016 (6) | 0.0092 (5) | 0.0011 (6) |
O88 | 0.0234 (7) | 0.0275 (8) | 0.0316 (7) | −0.0039 (6) | 0.0075 (6) | −0.0065 (6) |
O89 | 0.0204 (6) | 0.0323 (8) | 0.0249 (6) | −0.0008 (6) | 0.0087 (5) | −0.0017 (6) |
C60 | 0.0224 (10) | 0.0297 (11) | 0.0329 (10) | 0.0018 (8) | 0.0110 (8) | 0.0060 (9) |
N103 | 0.0355 (11) | 0.0439 (12) | 0.0476 (12) | −0.0080 (10) | 0.0206 (9) | −0.0012 (9) |
C65 | 0.0356 (12) | 0.0357 (13) | 0.0265 (10) | 0.0008 (9) | 0.0109 (9) | −0.0031 (9) |
C59 | 0.0222 (9) | 0.0272 (11) | 0.0237 (9) | 0.0044 (8) | 0.0088 (7) | 0.0034 (8) |
C67 | 0.0249 (10) | 0.0280 (11) | 0.0243 (9) | 0.0017 (8) | 0.0077 (8) | 0.0025 (8) |
C9 | 0.0357 (12) | 0.0412 (14) | 0.0422 (12) | −0.0003 (10) | 0.0216 (10) | −0.0022 (10) |
C31 | 0.0294 (11) | 0.0365 (13) | 0.0429 (12) | 0.0014 (10) | 0.0064 (9) | −0.0122 (10) |
C95 | 0.0467 (15) | 0.0451 (16) | 0.0746 (19) | −0.0030 (12) | 0.0220 (14) | 0.0226 (14) |
C63 | 0.0360 (12) | 0.0468 (14) | 0.0314 (11) | 0.0064 (10) | 0.0201 (9) | 0.0023 (10) |
C2 | 0.0355 (12) | 0.0403 (13) | 0.0299 (10) | 0.0004 (10) | 0.0130 (9) | 0.0043 (9) |
C101 | 0.0576 (16) | 0.0597 (18) | 0.0459 (14) | 0.0109 (14) | 0.0305 (12) | 0.0203 (13) |
C1 | 0.0261 (10) | 0.0342 (12) | 0.0279 (10) | −0.0023 (8) | 0.0132 (8) | −0.0002 (8) |
C80 | 0.0439 (14) | 0.0346 (13) | 0.0507 (14) | −0.0032 (11) | 0.0213 (11) | 0.0053 (11) |
C78 | 0.0291 (11) | 0.0280 (11) | 0.0317 (10) | −0.0039 (9) | 0.0125 (9) | −0.0017 (8) |
C68 | 0.0306 (11) | 0.0322 (12) | 0.0509 (13) | −0.0062 (9) | 0.0203 (10) | −0.0059 (10) |
C10 | 0.0430 (13) | 0.0419 (14) | 0.0360 (12) | 0.0126 (11) | 0.0136 (10) | 0.0101 (10) |
C61 | 0.0294 (11) | 0.0398 (13) | 0.0369 (11) | −0.0021 (9) | 0.0182 (9) | 0.0065 (10) |
C7 | 0.0596 (17) | 0.0669 (19) | 0.0478 (14) | 0.0052 (14) | 0.0366 (13) | −0.0071 (13) |
C3 | 0.0524 (15) | 0.0618 (18) | 0.0307 (12) | 0.0051 (13) | 0.0129 (11) | 0.0091 (11) |
C32 | 0.0316 (12) | 0.0425 (15) | 0.0608 (16) | −0.0035 (11) | 0.0056 (11) | −0.0195 (13) |
C93 | 0.0329 (13) | 0.0528 (17) | 0.0586 (16) | 0.0019 (11) | 0.0072 (11) | 0.0174 (13) |
C38 | 0.0357 (12) | 0.0292 (12) | 0.0440 (12) | 0.0005 (9) | 0.0127 (10) | −0.0048 (10) |
C30 | 0.0261 (10) | 0.0266 (11) | 0.0369 (11) | −0.0008 (8) | 0.0126 (9) | −0.0091 (9) |
C29 | 0.0382 (14) | 0.0532 (18) | 0.082 (2) | 0.0023 (12) | 0.0193 (14) | −0.0025 (15) |
C49 | 0.0549 (16) | 0.0299 (13) | 0.0459 (14) | −0.0032 (11) | 0.0026 (11) | 0.0021 (11) |
C20 | 0.0347 (12) | 0.0430 (14) | 0.0569 (15) | 0.0076 (11) | 0.0235 (11) | −0.0011 (12) |
C39 | 0.0416 (14) | 0.0435 (15) | 0.0439 (13) | −0.0003 (11) | −0.0077 (11) | −0.0048 (11) |
C99 | 0.0358 (14) | 0.099 (3) | 0.0499 (15) | 0.0187 (15) | 0.0156 (12) | 0.0258 (16) |
C36 | 0.0575 (16) | 0.0305 (13) | 0.0601 (16) | −0.0075 (12) | 0.0211 (13) | −0.0024 (12) |
C16 | 0.082 (2) | 0.0497 (18) | 0.0639 (18) | −0.0020 (16) | 0.0300 (16) | −0.0007 (15) |
C97 | 0.0319 (13) | 0.070 (2) | 0.0657 (17) | −0.0059 (13) | 0.0182 (12) | 0.0062 (15) |
C5 | 0.0707 (19) | 0.079 (2) | 0.0313 (12) | 0.0035 (16) | 0.0243 (12) | 0.0008 (13) |
C84 | 0.0376 (13) | 0.0407 (14) | 0.0424 (12) | −0.0099 (10) | 0.0109 (10) | −0.0080 (10) |
C22 | 0.0481 (16) | 0.0472 (18) | 0.110 (3) | 0.0069 (14) | 0.0232 (17) | −0.0050 (17) |
C34 | 0.0486 (15) | 0.0372 (15) | 0.0748 (19) | −0.0180 (12) | 0.0230 (14) | −0.0201 (14) |
C51 | 0.083 (3) | 0.211 (6) | 0.052 (2) | 0.009 (3) | 0.0088 (19) | 0.033 (3) |
C70 | 0.157 (4) | 0.0335 (16) | 0.084 (2) | −0.009 (2) | 0.076 (2) | −0.0045 (16) |
C12 | 0.0405 (17) | 0.077 (3) | 0.151 (4) | 0.0133 (16) | 0.019 (2) | −0.037 (3) |
C41 | 0.059 (2) | 0.097 (3) | 0.069 (2) | 0.0060 (18) | 0.0196 (16) | 0.0229 (19) |
C55 | 0.058 (2) | 0.156 (5) | 0.097 (3) | 0.037 (3) | −0.013 (2) | −0.037 (3) |
C45 | 0.0545 (19) | 0.089 (3) | 0.0574 (17) | 0.0221 (17) | −0.0020 (14) | 0.0033 (17) |
C74 | 0.0342 (16) | 0.097 (3) | 0.138 (3) | −0.0080 (17) | −0.0031 (19) | −0.068 (3) |
Geometric parameters (Å, º) top
S92—Si91 | 2.0239 (7) | C93—H93 | 0.93 |
Si91—O88 | 1.6439 (14) | C38—C36 | 1.392 (3) |
Si91—O90 | 1.6540 (14) | C38—C30 | 1.394 (3) |
Si91—O89 | 1.6550 (14) | C38—C49 | 1.528 (3) |
O90—C1 | 1.393 (2) | C29—C20 | 1.523 (4) |
O88—C30 | 1.381 (3) | C29—H29A | 0.96 |
O89—C59 | 1.380 (2) | C29—H29B | 0.96 |
C60—C61 | 1.386 (3) | C29—H29C | 0.96 |
C60—C59 | 1.397 (3) | C49—C51 | 1.495 (5) |
C60—C68 | 1.516 (3) | C49—C55 | 1.515 (5) |
N103—C101 | 1.312 (3) | C49—H49 | 0.98 |
N103—C93 | 1.321 (3) | C20—C22 | 1.514 (4) |
N103—H103 | 0.89 (3) | C20—H20 | 0.98 |
C65—C63 | 1.380 (3) | C39—C41 | 1.507 (4) |
C65—C67 | 1.396 (3) | C39—C45 | 1.522 (4) |
C65—H65 | 0.93 | C39—H39 | 0.98 |
C59—C67 | 1.405 (3) | C99—C97 | 1.358 (4) |
C67—C78 | 1.510 (3) | C99—H99 | 0.93 |
C9—C1 | 1.396 (3) | C36—C34 | 1.379 (4) |
C9—C7 | 1.403 (3) | C36—H36 | 0.93 |
C9—C20 | 1.509 (3) | C16—H16A | 0.96 |
C31—C32 | 1.384 (4) | C16—H16B | 0.96 |
C31—C30 | 1.411 (3) | C16—H16C | 0.96 |
C31—C39 | 1.510 (4) | C97—H97 | 0.93 |
C95—C93 | 1.363 (4) | C5—H5 | 0.93 |
C95—C97 | 1.369 (4) | C84—H84A | 0.96 |
C95—H95 | 0.93 | C84—H84B | 0.96 |
C63—C61 | 1.378 (3) | C84—H84C | 0.96 |
C63—H63 | 0.93 | C22—H22A | 0.96 |
C2—C3 | 1.393 (3) | C22—H22B | 0.96 |
C2—C1 | 1.402 (3) | C22—H22C | 0.96 |
C2—C10 | 1.508 (3) | C34—H34 | 0.93 |
C101—C99 | 1.371 (4) | C51—H51A | 0.96 |
C101—H101 | 0.93 | C51—H51B | 0.96 |
C80—C78 | 1.534 (3) | C51—H51C | 0.96 |
C80—H80A | 0.96 | C70—H70A | 0.96 |
C80—H80B | 0.96 | C70—H70B | 0.96 |
C80—H80C | 0.96 | C70—H70C | 0.96 |
C78—C84 | 1.532 (3) | C12—H12A | 0.96 |
C78—H78 | 0.98 | C12—H12B | 0.96 |
C68—C70 | 1.507 (4) | C12—H12C | 0.96 |
C68—C74 | 1.511 (4) | C41—H41A | 0.96 |
C68—H68 | 0.98 | C41—H41B | 0.96 |
C10—C12 | 1.504 (4) | C41—H41C | 0.96 |
C10—C16 | 1.525 (4) | C55—H55A | 0.96 |
C10—H10 | 0.98 | C55—H55B | 0.96 |
C61—H61 | 0.93 | C55—H55C | 0.96 |
C7—C5 | 1.377 (4) | C45—H45A | 0.96 |
C7—H7 | 0.93 | C45—H45B | 0.96 |
C3—C5 | 1.368 (4) | C45—H45C | 0.96 |
C3—H3 | 0.93 | C74—H74A | 0.96 |
C32—C34 | 1.375 (4) | C74—H74B | 0.96 |
C32—H32 | 0.93 | C74—H74C | 0.96 |
| | | |
O88—Si91—O90 | 102.36 (7) | H29B—C29—H29C | 109.5 |
O88—Si91—O89 | 106.76 (7) | C51—C49—C55 | 110.1 (3) |
O90—Si91—O89 | 105.68 (7) | C51—C49—C38 | 113.1 (3) |
O88—Si91—S92 | 116.61 (6) | C55—C49—C38 | 111.4 (2) |
O90—Si91—S92 | 111.07 (5) | C51—C49—H49 | 107.3 |
O89—Si91—S92 | 113.29 (5) | C55—C49—H49 | 107.3 |
C1—O90—Si91 | 130.63 (13) | C38—C49—H49 | 107.3 |
C30—O88—Si91 | 135.71 (13) | C9—C20—C22 | 111.5 (2) |
C59—O89—Si91 | 129.64 (12) | C9—C20—C29 | 111.4 (2) |
C61—C60—C59 | 118.3 (2) | C22—C20—C29 | 111.1 (2) |
C61—C60—C68 | 119.99 (19) | C9—C20—H20 | 107.6 |
C59—C60—C68 | 121.67 (19) | C22—C20—H20 | 107.6 |
C101—N103—C93 | 122.4 (2) | C29—C20—H20 | 107.6 |
C101—N103—H103 | 115.0 (18) | C41—C39—C31 | 110.4 (2) |
C93—N103—H103 | 122.6 (19) | C41—C39—C45 | 110.1 (2) |
C63—C65—C67 | 121.9 (2) | C31—C39—C45 | 113.3 (3) |
C63—C65—H65 | 119 | C41—C39—H39 | 107.6 |
C67—C65—H65 | 119 | C31—C39—H39 | 107.6 |
O89—C59—C60 | 117.81 (18) | C45—C39—H39 | 107.6 |
O89—C59—C67 | 120.67 (17) | C97—C99—C101 | 119.5 (2) |
C60—C59—C67 | 121.42 (18) | C97—C99—H99 | 120.3 |
C65—C67—C59 | 117.42 (19) | C101—C99—H99 | 120.3 |
C65—C67—C78 | 118.48 (19) | C34—C36—C38 | 121.5 (3) |
C59—C67—C78 | 123.92 (18) | C34—C36—H36 | 119.2 |
C1—C9—C7 | 116.7 (2) | C38—C36—H36 | 119.2 |
C1—C9—C20 | 122.6 (2) | C10—C16—H16A | 109.5 |
C7—C9—C20 | 120.7 (2) | C10—C16—H16B | 109.5 |
C32—C31—C30 | 117.5 (2) | H16A—C16—H16B | 109.5 |
C32—C31—C39 | 121.2 (2) | C10—C16—H16C | 109.5 |
C30—C31—C39 | 121.2 (2) | H16A—C16—H16C | 109.5 |
C93—C95—C97 | 119.2 (3) | H16B—C16—H16C | 109.5 |
C93—C95—H95 | 120.4 | C99—C97—C95 | 119.4 (3) |
C97—C95—H95 | 120.4 | C99—C97—H97 | 120.3 |
C61—C63—C65 | 119.1 (2) | C95—C97—H97 | 120.3 |
C61—C63—H63 | 120.4 | C3—C5—C7 | 119.5 (2) |
C65—C63—H63 | 120.4 | C3—C5—H5 | 120.2 |
C3—C2—C1 | 117.2 (2) | C7—C5—H5 | 120.2 |
C3—C2—C10 | 120.4 (2) | C78—C84—H84A | 109.5 |
C1—C2—C10 | 122.27 (19) | C78—C84—H84B | 109.5 |
N103—C101—C99 | 119.7 (3) | H84A—C84—H84B | 109.5 |
N103—C101—H101 | 120.2 | C78—C84—H84C | 109.5 |
C99—C101—H101 | 120.2 | H84A—C84—H84C | 109.5 |
O90—C1—C9 | 118.54 (19) | H84B—C84—H84C | 109.5 |
O90—C1—C2 | 118.68 (19) | C20—C22—H22A | 109.5 |
C9—C1—C2 | 122.7 (2) | C20—C22—H22B | 109.5 |
C78—C80—H80A | 109.5 | H22A—C22—H22B | 109.5 |
C78—C80—H80B | 109.5 | C20—C22—H22C | 109.5 |
H80A—C80—H80B | 109.5 | H22A—C22—H22C | 109.5 |
C78—C80—H80C | 109.5 | H22B—C22—H22C | 109.5 |
H80A—C80—H80C | 109.5 | C32—C34—C36 | 119.7 (2) |
H80B—C80—H80C | 109.5 | C32—C34—H34 | 120.1 |
C67—C78—C84 | 113.30 (18) | C36—C34—H34 | 120.1 |
C67—C78—C80 | 109.40 (18) | C49—C51—H51A | 109.5 |
C84—C78—C80 | 110.41 (19) | C49—C51—H51B | 109.5 |
C67—C78—H78 | 107.8 | H51A—C51—H51B | 109.5 |
C84—C78—H78 | 107.8 | C49—C51—H51C | 109.5 |
C80—C78—H78 | 107.8 | H51A—C51—H51C | 109.5 |
C70—C68—C74 | 111.5 (3) | H51B—C51—H51C | 109.5 |
C70—C68—C60 | 111.3 (2) | C68—C70—H70A | 109.5 |
C74—C68—C60 | 111.4 (2) | C68—C70—H70B | 109.5 |
C70—C68—H68 | 107.5 | H70A—C70—H70B | 109.5 |
C74—C68—H68 | 107.5 | C68—C70—H70C | 109.5 |
C60—C68—H68 | 107.5 | H70A—C70—H70C | 109.5 |
C12—C10—C2 | 113.4 (2) | H70B—C70—H70C | 109.5 |
C12—C10—C16 | 110.2 (3) | C10—C12—H12A | 109.5 |
C2—C10—C16 | 110.9 (2) | C10—C12—H12B | 109.5 |
C12—C10—H10 | 107.3 | H12A—C12—H12B | 109.5 |
C2—C10—H10 | 107.3 | C10—C12—H12C | 109.5 |
C16—C10—H10 | 107.3 | H12A—C12—H12C | 109.5 |
C63—C61—C60 | 121.7 (2) | H12B—C12—H12C | 109.5 |
C63—C61—H61 | 119.2 | C39—C41—H41A | 109.5 |
C60—C61—H61 | 119.2 | C39—C41—H41B | 109.5 |
C5—C7—C9 | 122.0 (3) | H41A—C41—H41B | 109.5 |
C5—C7—H7 | 119 | C39—C41—H41C | 109.5 |
C9—C7—H7 | 119 | H41A—C41—H41C | 109.5 |
C5—C3—C2 | 121.9 (2) | H41B—C41—H41C | 109.5 |
C5—C3—H3 | 119 | C49—C55—H55A | 109.5 |
C2—C3—H3 | 119 | C49—C55—H55B | 109.5 |
C34—C32—C31 | 121.7 (2) | H55A—C55—H55B | 109.5 |
C34—C32—H32 | 119.2 | C49—C55—H55C | 109.5 |
C31—C32—H32 | 119.2 | H55A—C55—H55C | 109.5 |
N103—C93—C95 | 119.9 (2) | H55B—C55—H55C | 109.5 |
N103—C93—H93 | 120.1 | C39—C45—H45A | 109.5 |
C95—C93—H93 | 120.1 | C39—C45—H45B | 109.5 |
C36—C38—C30 | 117.6 (2) | H45A—C45—H45B | 109.5 |
C36—C38—C49 | 119.9 (2) | C39—C45—H45C | 109.5 |
C30—C38—C49 | 122.5 (2) | H45A—C45—H45C | 109.5 |
O88—C30—C38 | 120.86 (18) | H45B—C45—H45C | 109.5 |
O88—C30—C31 | 117.0 (2) | C68—C74—H74A | 109.5 |
C38—C30—C31 | 122.0 (2) | C68—C74—H74B | 109.5 |
C20—C29—H29A | 109.5 | H74A—C74—H74B | 109.5 |
C20—C29—H29B | 109.5 | C68—C74—H74C | 109.5 |
H29A—C29—H29B | 109.5 | H74A—C74—H74C | 109.5 |
C20—C29—H29C | 109.5 | H74B—C74—H74C | 109.5 |
H29A—C29—H29C | 109.5 | | |
| | | |
O88—Si91—O90—C1 | −26.15 (18) | C1—C2—C10—C16 | −112.7 (3) |
O89—Si91—O90—C1 | 85.45 (17) | C65—C63—C61—C60 | −1.2 (3) |
S92—Si91—O90—C1 | −151.30 (15) | C59—C60—C61—C63 | −0.6 (3) |
O90—Si91—O88—C30 | 158.28 (18) | C68—C60—C61—C63 | 178.8 (2) |
O89—Si91—O88—C30 | 47.5 (2) | C1—C9—C7—C5 | 0.5 (4) |
S92—Si91—O88—C30 | −80.29 (19) | C20—C9—C7—C5 | 179.3 (3) |
O88—Si91—O89—C59 | −128.60 (16) | C1—C2—C3—C5 | 1.0 (4) |
O90—Si91—O89—C59 | 122.93 (16) | C10—C2—C3—C5 | −176.3 (3) |
S92—Si91—O89—C59 | 1.10 (18) | C30—C31—C32—C34 | 1.4 (4) |
Si91—O89—C59—C60 | 113.97 (18) | C39—C31—C32—C34 | −176.0 (2) |
Si91—O89—C59—C67 | −69.7 (2) | C101—N103—C93—C95 | −0.2 (4) |
C61—C60—C59—O89 | 179.30 (17) | C97—C95—C93—N103 | 1.2 (5) |
C68—C60—C59—O89 | −0.1 (3) | Si91—O88—C30—C38 | 83.2 (3) |
C61—C60—C59—C67 | 3.0 (3) | Si91—O88—C30—C31 | −100.9 (2) |
C68—C60—C59—C67 | −176.37 (19) | C36—C38—C30—O88 | 177.8 (2) |
C63—C65—C67—C59 | 1.7 (3) | C49—C38—C30—O88 | −1.0 (3) |
C63—C65—C67—C78 | −173.7 (2) | C36—C38—C30—C31 | 2.0 (3) |
O89—C59—C67—C65 | −179.73 (17) | C49—C38—C30—C31 | −176.8 (2) |
C60—C59—C67—C65 | −3.6 (3) | C32—C31—C30—O88 | −178.5 (2) |
O89—C59—C67—C78 | −4.6 (3) | C39—C31—C30—O88 | −1.2 (3) |
C60—C59—C67—C78 | 171.55 (19) | C32—C31—C30—C38 | −2.6 (3) |
C67—C65—C63—C61 | 0.6 (3) | C39—C31—C30—C38 | 174.8 (2) |
C93—N103—C101—C99 | −0.8 (4) | C36—C38—C49—C51 | 53.1 (4) |
Si91—O90—C1—C9 | 86.7 (2) | C30—C38—C49—C51 | −128.1 (3) |
Si91—O90—C1—C2 | −97.3 (2) | C36—C38—C49—C55 | −71.6 (4) |
C7—C9—C1—O90 | 177.4 (2) | C30—C38—C49—C55 | 107.2 (3) |
C20—C9—C1—O90 | −1.5 (3) | C1—C9—C20—C22 | −123.2 (3) |
C7—C9—C1—C2 | 1.6 (4) | C7—C9—C20—C22 | 57.9 (3) |
C20—C9—C1—C2 | −177.2 (2) | C1—C9—C20—C29 | 112.0 (3) |
C3—C2—C1—O90 | −178.1 (2) | C7—C9—C20—C29 | −66.8 (3) |
C10—C2—C1—O90 | −0.9 (3) | C32—C31—C39—C41 | 88.0 (3) |
C3—C2—C1—C9 | −2.4 (3) | C30—C31—C39—C41 | −89.2 (3) |
C10—C2—C1—C9 | 174.9 (2) | C32—C31—C39—C45 | −36.0 (3) |
C65—C67—C78—C84 | −55.0 (3) | C30—C31—C39—C45 | 146.7 (2) |
C59—C67—C78—C84 | 129.9 (2) | N103—C101—C99—C97 | 0.8 (5) |
C65—C67—C78—C80 | 68.7 (2) | C30—C38—C36—C34 | −0.3 (4) |
C59—C67—C78—C80 | −106.4 (2) | C49—C38—C36—C34 | 178.5 (3) |
C61—C60—C68—C70 | 68.5 (3) | C101—C99—C97—C95 | 0.2 (5) |
C59—C60—C68—C70 | −112.1 (3) | C93—C95—C97—C99 | −1.2 (5) |
C61—C60—C68—C74 | −56.7 (3) | C2—C3—C5—C7 | 1.0 (5) |
C59—C60—C68—C74 | 122.7 (3) | C9—C7—C5—C3 | −1.7 (5) |
C3—C2—C10—C12 | −60.2 (4) | C31—C32—C34—C36 | 0.3 (4) |
C1—C2—C10—C12 | 122.6 (3) | C38—C36—C34—C32 | −0.8 (4) |
C3—C2—C10—C16 | 64.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C101—H101···S92i | 0.93 | 2.88 | 3.330 (3) | 111 |
N103—H103···S92 | 0.89 (3) | 2.13 (3) | 3.019 (2) | 172 (3) |
Symmetry code: (i) −x+1, −y+1, −z. |
Crystal data top
C36H51O3SSi·C5H6N | F(000) = 1456 |
Mr = 672.02 | Dx = 1.121 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11321 reflections |
a = 13.4813 (14) Å | θ = 3.0–29.5° |
b = 16.3521 (10) Å | µ = 0.15 mm−1 |
c = 18.8926 (18) Å | T = 180 K |
β = 107.073 (8)° | Plate, colorless |
V = 3981.3 (6) Å3 | 0.38 × 0.31 × 0.15 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 5344 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.049 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.1° |
rotation method scans | h = −16→13 |
22334 measured reflections | k = −19→20 |
7795 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H 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 reflections | Δρmax = 0.49 e Å−3 |
440 parameters | Δρmin = −0.34 e Å−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 | x | y | z | Uiso*/Ueq | |
S92 | 0.59552 (4) | 0.52625 (3) | 0.09033 (3) | 0.02984 (13) | |
Si91 | 0.68596 (4) | 0.51559 (3) | 0.19646 (3) | 0.02243 (13) | |
O90 | 0.63001 (10) | 0.45687 (9) | 0.24521 (7) | 0.0255 (3) | |
O88 | 0.70919 (10) | 0.60025 (9) | 0.24582 (7) | 0.0277 (3) | |
O89 | 0.80002 (10) | 0.47279 (9) | 0.20391 (7) | 0.0255 (3) | |
C60 | 0.92779 (15) | 0.48645 (13) | 0.14028 (11) | 0.0278 (4) | |
N103 | 0.40577 (16) | 0.43768 (14) | 0.10528 (11) | 0.0407 (5) | |
C65 | 0.84637 (17) | 0.35142 (14) | 0.05295 (11) | 0.0323 (5) | |
H65 | 0.8197 | 0.3063 | 0.0235 | 0.039* | |
C59 | 0.84111 (15) | 0.44544 (13) | 0.14921 (10) | 0.0240 (4) | |
C67 | 0.80048 (15) | 0.37561 (13) | 0.10712 (10) | 0.0257 (4) | |
C9 | 0.57325 (18) | 0.50881 (15) | 0.34582 (13) | 0.0376 (5) | |
C31 | 0.86574 (17) | 0.66577 (15) | 0.31464 (13) | 0.0373 (5) | |
C95 | 0.3108 (2) | 0.33654 (18) | 0.14290 (17) | 0.0547 (7) | |
H95 | 0.3083 | 0.2916 | 0.1725 | 0.066* | |
C63 | 0.93019 (17) | 0.39253 (15) | 0.04191 (12) | 0.0360 (5) | |
H63 | 0.959 | 0.3757 | 0.0052 | 0.043* | |
C2 | 0.70701 (18) | 0.40185 (15) | 0.36717 (12) | 0.0346 (5) | |
C101 | 0.3216 (2) | 0.46921 (19) | 0.05955 (14) | 0.0512 (7) | |
H101 | 0.326 | 0.5152 | 0.0317 | 0.061* | |
C1 | 0.63842 (16) | 0.45715 (13) | 0.32060 (11) | 0.0283 (4) | |
C80 | 0.7644 (2) | 0.24127 (15) | 0.15647 (14) | 0.0415 (6) | |
H80A | 0.7896 | 0.211 | 0.1218 | 0.062* | |
H80B | 0.7126 | 0.2097 | 0.1698 | 0.062* | |
H80C | 0.8208 | 0.2526 | 0.2 | 0.062* | |
C78 | 0.71648 (16) | 0.32216 (13) | 0.12096 (11) | 0.0289 (4) | |
H78 | 0.6882 | 0.3505 | 0.1564 | 0.035* | |
C68 | 0.97583 (17) | 0.55878 (14) | 0.18862 (13) | 0.0362 (5) | |
H68 | 0.9396 | 0.5648 | 0.2263 | 0.043* | |
C10 | 0.77063 (19) | 0.34151 (15) | 0.33829 (13) | 0.0400 (6) | |
H10 | 0.7577 | 0.3526 | 0.2854 | 0.048* | |
C61 | 0.97049 (17) | 0.45895 (14) | 0.08605 (12) | 0.0336 (5) | |
H61 | 1.0277 | 0.486 | 0.0793 | 0.04* | |
C7 | 0.5812 (2) | 0.50460 (19) | 0.42157 (15) | 0.0538 (7) | |
H7 | 0.5387 | 0.5378 | 0.4402 | 0.065* | |
C3 | 0.7113 (2) | 0.40199 (18) | 0.44186 (13) | 0.0483 (6) | |
H3 | 0.7569 | 0.3666 | 0.4741 | 0.058* | |
C32 | 0.93213 (19) | 0.73218 (16) | 0.32308 (15) | 0.0469 (6) | |
H32 | 0.9924 | 0.7331 | 0.3628 | 0.056* | |
C93 | 0.40327 (19) | 0.37290 (17) | 0.14667 (15) | 0.0496 (7) | |
H93 | 0.4645 | 0.3522 | 0.1783 | 0.06* | |
C38 | 0.75224 (18) | 0.73130 (14) | 0.20324 (13) | 0.0362 (5) | |
C30 | 0.77625 (16) | 0.66582 (13) | 0.25280 (12) | 0.0292 (5) | |
C29 | 0.3847 (2) | 0.53916 (19) | 0.28675 (18) | 0.0575 (7) | |
H29A | 0.3747 | 0.4841 | 0.2684 | 0.086* | |
H29B | 0.3376 | 0.5749 | 0.2526 | 0.086* | |
H29C | 0.3719 | 0.5417 | 0.3341 | 0.086* | |
C49 | 0.6529 (2) | 0.73420 (16) | 0.13838 (14) | 0.0463 (6) | |
H49 | 0.6204 | 0.6801 | 0.1346 | 0.056* | |
C20 | 0.49605 (18) | 0.56564 (16) | 0.29500 (15) | 0.0428 (6) | |
H20 | 0.5068 | 0.5624 | 0.246 | 0.051* | |
C39 | 0.8858 (2) | 0.59768 (17) | 0.37127 (14) | 0.0475 (7) | |
H39 | 0.852 | 0.5483 | 0.346 | 0.057* | |
C99 | 0.2270 (2) | 0.4338 (2) | 0.05317 (15) | 0.0612 (8) | |
H99 | 0.167 | 0.4553 | 0.0205 | 0.073* | |
C36 | 0.8219 (2) | 0.79647 (16) | 0.21535 (16) | 0.0486 (6) | |
H36 | 0.8078 | 0.8407 | 0.183 | 0.058* | |
C16 | 0.7356 (3) | 0.25384 (19) | 0.34557 (18) | 0.0635 (8) | |
H16A | 0.7489 | 0.2405 | 0.397 | 0.095* | |
H16B | 0.7733 | 0.217 | 0.3234 | 0.095* | |
H16C | 0.6627 | 0.249 | 0.3209 | 0.095* | |
C97 | 0.2216 (2) | 0.3671 (2) | 0.09497 (16) | 0.0551 (7) | |
H97 | 0.158 | 0.3426 | 0.091 | 0.066* | |
C5 | 0.6502 (2) | 0.4527 (2) | 0.46907 (14) | 0.0585 (8) | |
H5 | 0.6553 | 0.4522 | 0.5192 | 0.07* | |
C84 | 0.62667 (18) | 0.30550 (16) | 0.05097 (13) | 0.0405 (6) | |
H84A | 0.5981 | 0.3565 | 0.029 | 0.061* | |
H84B | 0.5739 | 0.2745 | 0.0637 | 0.061* | |
H84C | 0.6518 | 0.275 | 0.0163 | 0.061* | |
C22 | 0.5137 (2) | 0.65377 (19) | 0.3207 (2) | 0.0684 (9) | |
H22A | 0.5049 | 0.6587 | 0.3691 | 0.103* | |
H22B | 0.4645 | 0.6884 | 0.2867 | 0.103* | |
H22C | 0.5828 | 0.67 | 0.3224 | 0.103* | |
C34 | 0.9113 (2) | 0.79690 (17) | 0.27426 (17) | 0.0526 (7) | |
H34 | 0.9572 | 0.8407 | 0.281 | 0.063* | |
C51 | 0.6723 (3) | 0.7514 (4) | 0.0657 (2) | 0.1182 (19) | |
H51A | 0.702 | 0.8049 | 0.0669 | 0.177* | |
H51B | 0.608 | 0.7489 | 0.0267 | 0.177* | |
H51C | 0.7195 | 0.7114 | 0.057 | 0.177* | |
C70 | 0.9606 (4) | 0.63715 (19) | 0.1445 (2) | 0.0829 (12) | |
H70A | 1 | 0.6349 | 0.1096 | 0.124* | |
H70B | 0.9838 | 0.6826 | 0.1774 | 0.124* | |
H70C | 0.8884 | 0.6438 | 0.1183 | 0.124* | |
C12 | 0.8856 (2) | 0.3496 (2) | 0.3745 (3) | 0.0917 (14) | |
H12A | 0.9071 | 0.4043 | 0.3679 | 0.138* | |
H12B | 0.9218 | 0.3116 | 0.3522 | 0.138* | |
H12C | 0.9011 | 0.3379 | 0.4264 | 0.138* | |
C41 | 0.8371 (3) | 0.6176 (3) | 0.43166 (19) | 0.0747 (10) | |
H41A | 0.8682 | 0.6663 | 0.457 | 0.112* | |
H41B | 0.8482 | 0.573 | 0.4662 | 0.112* | |
H41C | 0.7639 | 0.6262 | 0.4102 | 0.112* | |
C55 | 0.5761 (3) | 0.7956 (3) | 0.1521 (2) | 0.1118 (18) | |
H55A | 0.5604 | 0.7818 | 0.197 | 0.168* | |
H55B | 0.5135 | 0.7944 | 0.1114 | 0.168* | |
H55C | 0.6057 | 0.8494 | 0.1564 | 0.168* | |
C45 | 1.0006 (2) | 0.5784 (2) | 0.40480 (17) | 0.0713 (10) | |
H45A | 1.0318 | 0.5691 | 0.3659 | 0.107* | |
H45B | 1.0081 | 0.5303 | 0.435 | 0.107* | |
H45C | 1.0344 | 0.6236 | 0.4346 | 0.107* | |
C74 | 1.0892 (2) | 0.5439 (3) | 0.2286 (3) | 0.0963 (15) | |
H74A | 1.096 | 0.495 | 0.2578 | 0.144* | |
H74B | 1.1166 | 0.5895 | 0.2602 | 0.144* | |
H74C | 1.1269 | 0.5376 | 0.193 | 0.144* | |
H103 | 0.465 (2) | 0.4622 (18) | 0.1052 (15) | 0.053 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S92 | 0.0284 (3) | 0.0332 (3) | 0.0259 (2) | −0.0044 (2) | 0.00488 (19) | 0.0017 (2) |
Si91 | 0.0195 (3) | 0.0246 (3) | 0.0238 (2) | −0.0016 (2) | 0.0073 (2) | −0.0013 (2) |
O90 | 0.0238 (7) | 0.0296 (8) | 0.0246 (6) | −0.0015 (6) | 0.0092 (5) | 0.0011 (6) |
O88 | 0.0234 (7) | 0.0276 (8) | 0.0317 (7) | −0.0039 (6) | 0.0075 (6) | −0.0065 (6) |
O89 | 0.0204 (6) | 0.0325 (8) | 0.0250 (6) | −0.0007 (6) | 0.0087 (5) | −0.0017 (6) |
C60 | 0.0224 (10) | 0.0299 (11) | 0.0329 (10) | 0.0017 (8) | 0.0110 (8) | 0.0059 (9) |
N103 | 0.0355 (11) | 0.0441 (12) | 0.0477 (12) | −0.0080 (10) | 0.0205 (9) | −0.0011 (9) |
C65 | 0.0357 (12) | 0.0357 (13) | 0.0266 (10) | 0.0007 (9) | 0.0109 (9) | −0.0033 (9) |
C59 | 0.0222 (9) | 0.0273 (11) | 0.0238 (9) | 0.0042 (8) | 0.0087 (7) | 0.0035 (8) |
C67 | 0.0249 (10) | 0.0282 (11) | 0.0243 (9) | 0.0018 (8) | 0.0078 (8) | 0.0025 (8) |
C9 | 0.0356 (12) | 0.0415 (14) | 0.0423 (12) | −0.0004 (10) | 0.0215 (10) | −0.0023 (10) |
C31 | 0.0296 (11) | 0.0365 (13) | 0.0430 (12) | 0.0015 (10) | 0.0064 (9) | −0.0120 (10) |
C95 | 0.0466 (15) | 0.0453 (16) | 0.0748 (19) | −0.0030 (12) | 0.0222 (14) | 0.0227 (14) |
C63 | 0.0361 (12) | 0.0471 (14) | 0.0315 (11) | 0.0063 (10) | 0.0203 (9) | 0.0023 (10) |
C2 | 0.0355 (12) | 0.0406 (13) | 0.0300 (10) | 0.0003 (10) | 0.0131 (9) | 0.0044 (9) |
C101 | 0.0576 (16) | 0.0599 (18) | 0.0460 (14) | 0.0109 (14) | 0.0306 (12) | 0.0204 (13) |
C1 | 0.0261 (10) | 0.0343 (12) | 0.0279 (10) | −0.0021 (9) | 0.0133 (8) | −0.0001 (8) |
C80 | 0.0439 (14) | 0.0346 (13) | 0.0508 (14) | −0.0032 (11) | 0.0214 (11) | 0.0053 (11) |
C78 | 0.0291 (11) | 0.0281 (11) | 0.0317 (10) | −0.0039 (9) | 0.0124 (9) | −0.0019 (9) |
C68 | 0.0306 (11) | 0.0322 (12) | 0.0510 (13) | −0.0061 (9) | 0.0202 (10) | −0.0059 (10) |
C10 | 0.0430 (13) | 0.0423 (14) | 0.0361 (12) | 0.0125 (11) | 0.0136 (10) | 0.0102 (10) |
C61 | 0.0294 (11) | 0.0400 (13) | 0.0370 (11) | −0.0021 (9) | 0.0182 (9) | 0.0065 (10) |
C7 | 0.0597 (17) | 0.0674 (19) | 0.0477 (14) | 0.0053 (14) | 0.0366 (13) | −0.0072 (13) |
C3 | 0.0525 (16) | 0.0621 (18) | 0.0308 (12) | 0.0049 (13) | 0.0128 (11) | 0.0091 (11) |
C32 | 0.0317 (12) | 0.0427 (15) | 0.0610 (16) | −0.0036 (11) | 0.0055 (11) | −0.0196 (13) |
C93 | 0.0330 (13) | 0.0531 (17) | 0.0588 (16) | 0.0021 (11) | 0.0071 (11) | 0.0176 (13) |
C38 | 0.0357 (12) | 0.0294 (12) | 0.0441 (13) | 0.0005 (9) | 0.0127 (10) | −0.0048 (10) |
C30 | 0.0261 (10) | 0.0268 (11) | 0.0370 (11) | −0.0007 (8) | 0.0125 (9) | −0.0090 (9) |
C29 | 0.0383 (14) | 0.0535 (18) | 0.082 (2) | 0.0024 (12) | 0.0193 (14) | −0.0025 (15) |
C49 | 0.0549 (16) | 0.0300 (13) | 0.0460 (14) | −0.0031 (11) | 0.0026 (12) | 0.0022 (11) |
C20 | 0.0347 (13) | 0.0431 (14) | 0.0569 (15) | 0.0075 (11) | 0.0234 (11) | −0.0012 (12) |
C39 | 0.0416 (14) | 0.0437 (15) | 0.0440 (14) | −0.0003 (11) | −0.0078 (11) | −0.0047 (11) |
C99 | 0.0358 (14) | 0.100 (3) | 0.0501 (15) | 0.0187 (15) | 0.0156 (12) | 0.0259 (16) |
C36 | 0.0576 (17) | 0.0305 (13) | 0.0603 (16) | −0.0076 (12) | 0.0212 (13) | −0.0023 (12) |
C16 | 0.082 (2) | 0.0499 (18) | 0.0640 (18) | −0.0020 (16) | 0.0301 (16) | −0.0007 (15) |
C97 | 0.0319 (13) | 0.070 (2) | 0.0657 (17) | −0.0058 (13) | 0.0183 (12) | 0.0063 (15) |
C5 | 0.0706 (19) | 0.080 (2) | 0.0314 (12) | 0.0035 (16) | 0.0244 (13) | 0.0008 (13) |
C84 | 0.0376 (13) | 0.0410 (14) | 0.0425 (13) | −0.0099 (10) | 0.0110 (10) | −0.0080 (10) |
C22 | 0.0482 (17) | 0.0475 (18) | 0.110 (3) | 0.0070 (14) | 0.0234 (17) | −0.0050 (17) |
C34 | 0.0486 (15) | 0.0372 (15) | 0.0751 (19) | −0.0182 (12) | 0.0228 (14) | −0.0203 (14) |
C51 | 0.083 (3) | 0.212 (6) | 0.052 (2) | 0.009 (3) | 0.0088 (19) | 0.033 (3) |
C70 | 0.157 (4) | 0.0336 (16) | 0.084 (2) | −0.009 (2) | 0.076 (2) | −0.0046 (16) |
C12 | 0.0405 (17) | 0.077 (3) | 0.151 (4) | 0.0132 (16) | 0.019 (2) | −0.037 (3) |
C41 | 0.059 (2) | 0.097 (3) | 0.069 (2) | 0.0062 (18) | 0.0195 (16) | 0.0230 (19) |
C55 | 0.058 (2) | 0.157 (5) | 0.097 (3) | 0.037 (3) | −0.013 (2) | −0.037 (3) |
C45 | 0.0548 (19) | 0.090 (3) | 0.0576 (18) | 0.0221 (17) | −0.0022 (14) | 0.0033 (17) |
C74 | 0.0343 (16) | 0.097 (3) | 0.139 (3) | −0.0081 (17) | −0.0032 (19) | −0.068 (3) |
Geometric parameters (Å, º) top
S92—Si91 | 2.0252 (7) | C93—H93 | 0.93 |
Si91—O88 | 1.6469 (14) | C38—C36 | 1.394 (3) |
Si91—O89 | 1.6574 (14) | C38—C30 | 1.396 (3) |
Si91—O90 | 1.6575 (14) | C38—C49 | 1.528 (3) |
O90—C1 | 1.395 (2) | C29—C20 | 1.525 (4) |
O88—C30 | 1.384 (3) | C29—H29A | 0.96 |
O89—C59 | 1.382 (2) | C29—H29B | 0.96 |
C60—C61 | 1.389 (3) | C29—H29C | 0.96 |
C60—C59 | 1.400 (3) | C49—C51 | 1.498 (5) |
C60—C68 | 1.518 (3) | C49—C55 | 1.518 (5) |
N103—C101 | 1.313 (3) | C49—H49 | 0.98 |
N103—C93 | 1.323 (3) | C20—C22 | 1.517 (4) |
N103—H103 | 0.89 (3) | C20—H20 | 0.98 |
C65—C63 | 1.382 (3) | C39—C41 | 1.510 (4) |
C65—C67 | 1.399 (3) | C39—C45 | 1.524 (4) |
C65—H65 | 0.93 | C39—H39 | 0.98 |
C59—C67 | 1.407 (3) | C99—C97 | 1.361 (4) |
C67—C78 | 1.513 (3) | C99—H99 | 0.93 |
C9—C1 | 1.399 (3) | C36—C34 | 1.379 (4) |
C9—C7 | 1.405 (3) | C36—H36 | 0.93 |
C9—C20 | 1.511 (3) | C16—H16A | 0.96 |
C31—C32 | 1.386 (4) | C16—H16B | 0.96 |
C31—C30 | 1.412 (3) | C16—H16C | 0.96 |
C31—C39 | 1.512 (4) | C97—H97 | 0.93 |
C95—C93 | 1.364 (4) | C5—H5 | 0.93 |
C95—C97 | 1.370 (4) | C84—H84A | 0.96 |
C95—H95 | 0.93 | C84—H84B | 0.96 |
C63—C61 | 1.380 (3) | C84—H84C | 0.96 |
C63—H63 | 0.93 | C22—H22A | 0.96 |
C2—C3 | 1.395 (3) | C22—H22B | 0.96 |
C2—C1 | 1.403 (3) | C22—H22C | 0.96 |
C2—C10 | 1.510 (3) | C34—H34 | 0.93 |
C101—C99 | 1.373 (4) | C51—H51A | 0.96 |
C101—H101 | 0.93 | C51—H51B | 0.96 |
C80—C78 | 1.537 (3) | C51—H51C | 0.96 |
C80—H80A | 0.96 | C70—H70A | 0.96 |
C80—H80B | 0.96 | C70—H70B | 0.96 |
C80—H80C | 0.96 | C70—H70C | 0.96 |
C78—C84 | 1.533 (3) | C12—H12A | 0.96 |
C78—H78 | 0.98 | C12—H12B | 0.96 |
C68—C70 | 1.510 (4) | C12—H12C | 0.96 |
C68—C74 | 1.512 (4) | C41—H41A | 0.96 |
C68—H68 | 0.98 | C41—H41B | 0.96 |
C10—C12 | 1.505 (4) | C41—H41C | 0.96 |
C10—C16 | 1.528 (4) | C55—H55A | 0.96 |
C10—H10 | 0.98 | C55—H55B | 0.96 |
C61—H61 | 0.93 | C55—H55C | 0.96 |
C7—C5 | 1.378 (4) | C45—H45A | 0.96 |
C7—H7 | 0.93 | C45—H45B | 0.96 |
C3—C5 | 1.371 (4) | C45—H45C | 0.96 |
C3—H3 | 0.93 | C74—H74A | 0.96 |
C32—C34 | 1.377 (4) | C74—H74B | 0.96 |
C32—H32 | 0.93 | C74—H74C | 0.96 |
| | | |
O88—Si91—O89 | 106.82 (7) | H29B—C29—H29C | 109.5 |
O88—Si91—O90 | 102.37 (7) | C51—C49—C55 | 110.1 (3) |
O89—Si91—O90 | 105.69 (7) | C51—C49—C38 | 113.1 (3) |
O88—Si91—S92 | 116.57 (6) | C55—C49—C38 | 111.4 (2) |
O89—Si91—S92 | 113.22 (5) | C51—C49—H49 | 107.3 |
O90—Si91—S92 | 111.10 (5) | C55—C49—H49 | 107.3 |
C1—O90—Si91 | 130.65 (13) | C38—C49—H49 | 107.3 |
C30—O88—Si91 | 135.70 (13) | C9—C20—C22 | 111.5 (2) |
C59—O89—Si91 | 129.68 (12) | C9—C20—C29 | 111.3 (2) |
C61—C60—C59 | 118.4 (2) | C22—C20—C29 | 111.1 (2) |
C61—C60—C68 | 119.99 (19) | C9—C20—H20 | 107.6 |
C59—C60—C68 | 121.64 (19) | C22—C20—H20 | 107.6 |
C101—N103—C93 | 122.4 (2) | C29—C20—H20 | 107.6 |
C101—N103—H103 | 114.9 (18) | C41—C39—C31 | 110.4 (2) |
C93—N103—H103 | 122.7 (19) | C41—C39—C45 | 110.2 (2) |
C63—C65—C67 | 122.0 (2) | C31—C39—C45 | 113.3 (3) |
C63—C65—H65 | 119 | C41—C39—H39 | 107.6 |
C67—C65—H65 | 119 | C31—C39—H39 | 107.6 |
O89—C59—C60 | 117.84 (18) | C45—C39—H39 | 107.6 |
O89—C59—C67 | 120.67 (17) | C97—C99—C101 | 119.5 (2) |
C60—C59—C67 | 121.39 (18) | C97—C99—H99 | 120.2 |
C65—C67—C59 | 117.41 (19) | C101—C99—H99 | 120.2 |
C65—C67—C78 | 118.51 (19) | C34—C36—C38 | 121.5 (3) |
C59—C67—C78 | 123.91 (18) | C34—C36—H36 | 119.2 |
C1—C9—C7 | 116.7 (2) | C38—C36—H36 | 119.2 |
C1—C9—C20 | 122.6 (2) | C10—C16—H16A | 109.5 |
C7—C9—C20 | 120.7 (2) | C10—C16—H16B | 109.5 |
C32—C31—C30 | 117.4 (2) | H16A—C16—H16B | 109.5 |
C32—C31—C39 | 121.3 (2) | C10—C16—H16C | 109.5 |
C30—C31—C39 | 121.2 (2) | H16A—C16—H16C | 109.5 |
C93—C95—C97 | 119.1 (3) | H16B—C16—H16C | 109.5 |
C93—C95—H95 | 120.4 | C99—C97—C95 | 119.4 (3) |
C97—C95—H95 | 120.4 | C99—C97—H97 | 120.3 |
C61—C63—C65 | 119.1 (2) | C95—C97—H97 | 120.3 |
C61—C63—H63 | 120.5 | C3—C5—C7 | 119.5 (2) |
C65—C63—H63 | 120.5 | C3—C5—H5 | 120.2 |
C3—C2—C1 | 117.2 (2) | C7—C5—H5 | 120.2 |
C3—C2—C10 | 120.5 (2) | C78—C84—H84A | 109.5 |
C1—C2—C10 | 122.28 (19) | C78—C84—H84B | 109.5 |
N103—C101—C99 | 119.6 (3) | H84A—C84—H84B | 109.5 |
N103—C101—H101 | 120.2 | C78—C84—H84C | 109.5 |
C99—C101—H101 | 120.2 | H84A—C84—H84C | 109.5 |
O90—C1—C9 | 118.59 (19) | H84B—C84—H84C | 109.5 |
O90—C1—C2 | 118.62 (19) | C20—C22—H22A | 109.5 |
C9—C1—C2 | 122.7 (2) | C20—C22—H22B | 109.5 |
C78—C80—H80A | 109.5 | H22A—C22—H22B | 109.5 |
C78—C80—H80B | 109.5 | C20—C22—H22C | 109.5 |
H80A—C80—H80B | 109.5 | H22A—C22—H22C | 109.5 |
C78—C80—H80C | 109.5 | H22B—C22—H22C | 109.5 |
H80A—C80—H80C | 109.5 | C32—C34—C36 | 119.7 (2) |
H80B—C80—H80C | 109.5 | C32—C34—H34 | 120.2 |
C67—C78—C84 | 113.28 (18) | C36—C34—H34 | 120.2 |
C67—C78—C80 | 109.44 (18) | C49—C51—H51A | 109.5 |
C84—C78—C80 | 110.35 (19) | C49—C51—H51B | 109.5 |
C67—C78—H78 | 107.9 | H51A—C51—H51B | 109.5 |
C84—C78—H78 | 107.9 | C49—C51—H51C | 109.5 |
C80—C78—H78 | 107.9 | H51A—C51—H51C | 109.5 |
C70—C68—C74 | 111.5 (3) | H51B—C51—H51C | 109.5 |
C70—C68—C60 | 111.4 (2) | C68—C70—H70A | 109.5 |
C74—C68—C60 | 111.4 (2) | C68—C70—H70B | 109.5 |
C70—C68—H68 | 107.5 | H70A—C70—H70B | 109.5 |
C74—C68—H68 | 107.5 | C68—C70—H70C | 109.5 |
C60—C68—H68 | 107.5 | H70A—C70—H70C | 109.5 |
C12—C10—C2 | 113.4 (2) | H70B—C70—H70C | 109.5 |
C12—C10—C16 | 110.2 (3) | C10—C12—H12A | 109.5 |
C2—C10—C16 | 110.9 (2) | C10—C12—H12B | 109.5 |
C12—C10—H10 | 107.3 | H12A—C12—H12B | 109.5 |
C2—C10—H10 | 107.3 | C10—C12—H12C | 109.5 |
C16—C10—H10 | 107.3 | H12A—C12—H12C | 109.5 |
C63—C61—C60 | 121.7 (2) | H12B—C12—H12C | 109.5 |
C63—C61—H61 | 119.1 | C39—C41—H41A | 109.5 |
C60—C61—H61 | 119.1 | C39—C41—H41B | 109.5 |
C5—C7—C9 | 121.9 (3) | H41A—C41—H41B | 109.5 |
C5—C7—H7 | 119 | C39—C41—H41C | 109.5 |
C9—C7—H7 | 119 | H41A—C41—H41C | 109.5 |
C5—C3—C2 | 122.0 (2) | H41B—C41—H41C | 109.5 |
C5—C3—H3 | 119 | C49—C55—H55A | 109.5 |
C2—C3—H3 | 119 | C49—C55—H55B | 109.5 |
C34—C32—C31 | 121.8 (2) | H55A—C55—H55B | 109.5 |
C34—C32—H32 | 119.1 | C49—C55—H55C | 109.5 |
C31—C32—H32 | 119.1 | H55A—C55—H55C | 109.5 |
N103—C93—C95 | 120.0 (2) | H55B—C55—H55C | 109.5 |
N103—C93—H93 | 120 | C39—C45—H45A | 109.5 |
C95—C93—H93 | 120 | C39—C45—H45B | 109.5 |
C36—C38—C30 | 117.6 (2) | H45A—C45—H45B | 109.5 |
C36—C38—C49 | 119.8 (2) | C39—C45—H45C | 109.5 |
C30—C38—C49 | 122.5 (2) | H45A—C45—H45C | 109.5 |
O88—C30—C38 | 120.93 (18) | H45B—C45—H45C | 109.5 |
O88—C30—C31 | 117.0 (2) | C68—C74—H74A | 109.5 |
C38—C30—C31 | 121.9 (2) | C68—C74—H74B | 109.5 |
C20—C29—H29A | 109.5 | H74A—C74—H74B | 109.5 |
C20—C29—H29B | 109.5 | C68—C74—H74C | 109.5 |
H29A—C29—H29B | 109.5 | H74A—C74—H74C | 109.5 |
C20—C29—H29C | 109.5 | H74B—C74—H74C | 109.5 |
H29A—C29—H29C | 109.5 | | |
| | | |
O88—Si91—O90—C1 | −26.14 (18) | C1—C2—C10—C16 | −112.8 (3) |
O89—Si91—O90—C1 | 85.54 (17) | C65—C63—C61—C60 | −1.2 (3) |
S92—Si91—O90—C1 | −151.27 (15) | C59—C60—C61—C63 | −0.6 (3) |
O89—Si91—O88—C30 | 47.5 (2) | C68—C60—C61—C63 | 178.8 (2) |
O90—Si91—O88—C30 | 158.30 (18) | C1—C9—C7—C5 | 0.5 (4) |
S92—Si91—O88—C30 | −80.25 (19) | C20—C9—C7—C5 | 179.3 (3) |
O88—Si91—O89—C59 | −128.56 (16) | C1—C2—C3—C5 | 1.1 (4) |
O90—Si91—O89—C59 | 122.94 (16) | C10—C2—C3—C5 | −176.2 (3) |
S92—Si91—O89—C59 | 1.11 (18) | C30—C31—C32—C34 | 1.4 (4) |
Si91—O89—C59—C60 | 113.90 (18) | C39—C31—C32—C34 | −176.0 (3) |
Si91—O89—C59—C67 | −69.8 (2) | C101—N103—C93—C95 | −0.2 (4) |
C61—C60—C59—O89 | 179.29 (17) | C97—C95—C93—N103 | 1.2 (5) |
C68—C60—C59—O89 | −0.1 (3) | Si91—O88—C30—C38 | 83.2 (3) |
C61—C60—C59—C67 | 3.0 (3) | Si91—O88—C30—C31 | −100.9 (2) |
C68—C60—C59—C67 | −176.35 (19) | C36—C38—C30—O88 | 177.8 (2) |
C63—C65—C67—C59 | 1.7 (3) | C49—C38—C30—O88 | −1.0 (3) |
C63—C65—C67—C78 | −173.7 (2) | C36—C38—C30—C31 | 2.1 (3) |
O89—C59—C67—C65 | −179.73 (17) | C49—C38—C30—C31 | −176.7 (2) |
C60—C59—C67—C65 | −3.6 (3) | C32—C31—C30—O88 | −178.5 (2) |
O89—C59—C67—C78 | −4.6 (3) | C39—C31—C30—O88 | −1.1 (3) |
C60—C59—C67—C78 | 171.57 (19) | C32—C31—C30—C38 | −2.6 (3) |
C67—C65—C63—C61 | 0.6 (3) | C39—C31—C30—C38 | 174.8 (2) |
C93—N103—C101—C99 | −0.8 (4) | C36—C38—C49—C51 | 53.1 (4) |
Si91—O90—C1—C9 | 86.7 (2) | C30—C38—C49—C51 | −128.1 (3) |
Si91—O90—C1—C2 | −97.4 (2) | C36—C38—C49—C55 | −71.6 (4) |
C7—C9—C1—O90 | 177.4 (2) | C30—C38—C49—C55 | 107.2 (3) |
C20—C9—C1—O90 | −1.5 (3) | C1—C9—C20—C22 | −123.2 (3) |
C7—C9—C1—C2 | 1.6 (4) | C7—C9—C20—C22 | 58.0 (3) |
C20—C9—C1—C2 | −177.2 (2) | C1—C9—C20—C29 | 112.1 (3) |
C3—C2—C1—O90 | −178.1 (2) | C7—C9—C20—C29 | −66.7 (3) |
C10—C2—C1—O90 | −0.9 (3) | C32—C31—C39—C41 | 88.0 (3) |
C3—C2—C1—C9 | −2.4 (3) | C30—C31—C39—C41 | −89.2 (3) |
C10—C2—C1—C9 | 174.9 (2) | C32—C31—C39—C45 | −36.1 (3) |
C65—C67—C78—C84 | −55.0 (3) | C30—C31—C39—C45 | 146.7 (2) |
C59—C67—C78—C84 | 129.9 (2) | N103—C101—C99—C97 | 0.8 (5) |
C65—C67—C78—C80 | 68.6 (2) | C30—C38—C36—C34 | −0.3 (4) |
C59—C67—C78—C80 | −106.5 (2) | C49—C38—C36—C34 | 178.5 (3) |
C61—C60—C68—C70 | 68.4 (3) | C101—C99—C97—C95 | 0.2 (5) |
C59—C60—C68—C70 | −112.2 (3) | C93—C95—C97—C99 | −1.1 (5) |
C61—C60—C68—C74 | −56.7 (3) | C2—C3—C5—C7 | 0.9 (5) |
C59—C60—C68—C74 | 122.7 (3) | C9—C7—C5—C3 | −1.7 (5) |
C3—C2—C10—C12 | −60.3 (4) | C31—C32—C34—C36 | 0.3 (4) |
C1—C2—C10—C12 | 122.5 (3) | C38—C36—C34—C32 | −0.8 (4) |
C3—C2—C10—C16 | 64.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C101—H101···S92i | 0.93 | 2.89 | 3.336 (3) | 111 |
N103—H103···S92 | 0.89 (3) | 2.14 (3) | 3.024 (2) | 172 (3) |
Symmetry code: (i) −x+1, −y+1, −z. |
Crystal data top
C36H51O3SSi·C5H6N | F(000) = 1456 |
Mr = 672.02 | Dx = 1.114 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11992 reflections |
a = 13.5052 (13) Å | θ = 3–29.4° |
b = 16.382 (1) Å | µ = 0.15 mm−1 |
c = 18.9409 (18) Å | T = 210 K |
β = 107.106 (7)° | Plate, colorless |
V = 4005.1 (6) Å3 | 0.38 × 0.31 × 0.15 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 4399 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.066 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26°, θmin = 3.1° |
rotation method scans | h = −13→16 |
22528 measured reflections | k = −20→20 |
7841 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H 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 reflections | Δρmax = 0.31 e Å−3 |
440 parameters | Δρmin = −0.31 e Å−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 | x | y | z | Uiso*/Ueq | |
S92 | 0.59524 (5) | 0.52640 (5) | 0.09064 (3) | 0.03577 (18) | |
Si91 | 0.68620 (5) | 0.51613 (5) | 0.19644 (4) | 0.02701 (17) | |
O90 | 0.63079 (13) | 0.45791 (11) | 0.24549 (8) | 0.0301 (4) | |
O88 | 0.70985 (13) | 0.60078 (11) | 0.24550 (9) | 0.0327 (4) | |
O89 | 0.79972 (12) | 0.47322 (11) | 0.20388 (8) | 0.0297 (4) | |
C60 | 0.92693 (19) | 0.48708 (17) | 0.14009 (13) | 0.0315 (6) | |
N103 | 0.4057 (2) | 0.43769 (18) | 0.10531 (15) | 0.0484 (7) | |
C65 | 0.8459 (2) | 0.35176 (19) | 0.05341 (14) | 0.0387 (7) | |
H65 | 0.8196 | 0.3064 | 0.0245 | 0.046* | |
C59 | 0.84067 (19) | 0.44578 (16) | 0.14901 (13) | 0.0274 (5) | |
C67 | 0.8002 (2) | 0.37621 (16) | 0.10702 (13) | 0.0311 (6) | |
C9 | 0.5740 (2) | 0.5096 (2) | 0.34572 (16) | 0.0447 (7) | |
C31 | 0.8657 (2) | 0.66625 (19) | 0.31437 (16) | 0.0431 (7) | |
C95 | 0.3109 (3) | 0.3379 (2) | 0.1437 (2) | 0.0640 (10) | |
H95 | 0.3084 | 0.2935 | 0.1737 | 0.077* | |
C63 | 0.9290 (2) | 0.3927 (2) | 0.04195 (15) | 0.0434 (7) | |
H63 | 0.9575 | 0.3758 | 0.0053 | 0.052* | |
C2 | 0.7070 (2) | 0.40291 (19) | 0.36708 (14) | 0.0408 (7) | |
C101 | 0.3216 (3) | 0.4686 (2) | 0.05961 (17) | 0.0588 (9) | |
H101 | 0.3259 | 0.514 | 0.0311 | 0.071* | |
C1 | 0.6391 (2) | 0.45814 (17) | 0.32071 (13) | 0.0334 (6) | |
C80 | 0.7640 (3) | 0.24220 (19) | 0.15656 (18) | 0.0496 (8) | |
H80A | 0.7889 | 0.2117 | 0.122 | 0.074* | |
H80B | 0.7125 | 0.2109 | 0.1703 | 0.074* | |
H80C | 0.8206 | 0.2537 | 0.1998 | 0.074* | |
C78 | 0.7163 (2) | 0.32239 (17) | 0.12103 (14) | 0.0343 (6) | |
H78 | 0.6879 | 0.3507 | 0.1563 | 0.041* | |
C68 | 0.9749 (2) | 0.55907 (18) | 0.18758 (17) | 0.0428 (7) | |
H68 | 0.9381 | 0.5657 | 0.2247 | 0.051* | |
C10 | 0.7704 (2) | 0.3426 (2) | 0.33887 (16) | 0.0468 (8) | |
H10 | 0.7575 | 0.3536 | 0.2861 | 0.056* | |
C61 | 0.9692 (2) | 0.45900 (19) | 0.08557 (15) | 0.0398 (7) | |
H61 | 1.0263 | 0.4859 | 0.0786 | 0.048* | |
C7 | 0.5822 (3) | 0.5057 (3) | 0.42166 (19) | 0.0652 (10) | |
H7 | 0.54 | 0.5388 | 0.4404 | 0.078* | |
C3 | 0.7114 (3) | 0.4034 (2) | 0.44184 (16) | 0.0581 (9) | |
H3 | 0.757 | 0.3682 | 0.4742 | 0.07* | |
C32 | 0.9321 (2) | 0.7325 (2) | 0.3228 (2) | 0.0546 (9) | |
H32 | 0.992 | 0.7335 | 0.3627 | 0.066* | |
C93 | 0.4033 (3) | 0.3737 (2) | 0.14691 (19) | 0.0593 (9) | |
H93 | 0.4646 | 0.3531 | 0.1784 | 0.071* | |
C38 | 0.7536 (2) | 0.73133 (19) | 0.20259 (16) | 0.0443 (7) | |
C30 | 0.7773 (2) | 0.66615 (17) | 0.25278 (14) | 0.0333 (6) | |
C29 | 0.3853 (3) | 0.5403 (2) | 0.2867 (2) | 0.0682 (10) | |
H29A | 0.3756 | 0.4846 | 0.2703 | 0.102* | |
H29B | 0.3386 | 0.5747 | 0.251 | 0.102* | |
H29C | 0.3714 | 0.5452 | 0.3334 | 0.102* | |
C49 | 0.6545 (3) | 0.7344 (2) | 0.13784 (17) | 0.0558 (9) | |
H49 | 0.6228 | 0.6801 | 0.1336 | 0.067* | |
C20 | 0.4966 (2) | 0.5661 (2) | 0.29514 (19) | 0.0502 (8) | |
H20 | 0.5071 | 0.5626 | 0.2462 | 0.06* | |
C39 | 0.8854 (3) | 0.5987 (2) | 0.37133 (17) | 0.0556 (9) | |
H39 | 0.8508 | 0.5495 | 0.3465 | 0.067* | |
C99 | 0.2276 (3) | 0.4340 (3) | 0.05409 (19) | 0.0701 (12) | |
H99 | 0.1676 | 0.4556 | 0.0218 | 0.084* | |
C36 | 0.8230 (3) | 0.7963 (2) | 0.2155 (2) | 0.0571 (9) | |
H36 | 0.8088 | 0.8408 | 0.1837 | 0.069* | |
C16 | 0.7348 (4) | 0.2552 (2) | 0.3457 (2) | 0.0755 (11) | |
H16A | 0.7466 | 0.2421 | 0.3969 | 0.113* | |
H16B | 0.7732 | 0.2183 | 0.3244 | 0.113* | |
H16C | 0.6623 | 0.2505 | 0.32 | 0.113* | |
C97 | 0.2225 (3) | 0.3678 (3) | 0.0960 (2) | 0.0657 (10) | |
H97 | 0.1591 | 0.3432 | 0.0921 | 0.079* | |
C5 | 0.6511 (3) | 0.4540 (3) | 0.46846 (19) | 0.0720 (12) | |
H5 | 0.6565 | 0.4536 | 0.5186 | 0.086* | |
C84 | 0.6272 (2) | 0.3059 (2) | 0.05143 (17) | 0.0486 (8) | |
H84A | 0.5989 | 0.3568 | 0.0294 | 0.073* | |
H84B | 0.5743 | 0.2752 | 0.0641 | 0.073* | |
H84C | 0.6523 | 0.2753 | 0.017 | 0.073* | |
C22 | 0.5136 (3) | 0.6547 (2) | 0.3200 (3) | 0.0788 (12) | |
H22A | 0.5034 | 0.6603 | 0.3678 | 0.118* | |
H22B | 0.4651 | 0.6888 | 0.2852 | 0.118* | |
H22C | 0.5829 | 0.6707 | 0.3226 | 0.118* | |
C34 | 0.9118 (3) | 0.7964 (2) | 0.2740 (2) | 0.0610 (10) | |
H34 | 0.9581 | 0.8398 | 0.2805 | 0.073* | |
C51 | 0.6746 (4) | 0.7523 (5) | 0.0654 (2) | 0.135 (3) | |
H51A | 0.7031 | 0.8061 | 0.0667 | 0.203* | |
H51B | 0.6107 | 0.7491 | 0.0261 | 0.203* | |
H51C | 0.7227 | 0.713 | 0.057 | 0.203* | |
C70 | 0.9608 (5) | 0.6370 (2) | 0.1435 (2) | 0.0958 (16) | |
H70A | 1.0029 | 0.6354 | 0.1106 | 0.144* | |
H70B | 0.9811 | 0.6826 | 0.1764 | 0.144* | |
H70C | 0.8893 | 0.6427 | 0.1153 | 0.144* | |
C12 | 0.8856 (3) | 0.3500 (3) | 0.3745 (3) | 0.1072 (18) | |
H12A | 0.9077 | 0.4042 | 0.3669 | 0.161* | |
H12B | 0.921 | 0.3111 | 0.3527 | 0.161* | |
H12C | 0.9014 | 0.3395 | 0.4265 | 0.161* | |
C41 | 0.8379 (3) | 0.6192 (3) | 0.4322 (2) | 0.0891 (14) | |
H41A | 0.8698 | 0.6676 | 0.4575 | 0.134* | |
H41B | 0.8487 | 0.5746 | 0.4665 | 0.134* | |
H41C | 0.7649 | 0.6284 | 0.4112 | 0.134* | |
C55 | 0.5762 (4) | 0.7946 (4) | 0.1516 (3) | 0.129 (2) | |
H55A | 0.5608 | 0.7803 | 0.1964 | 0.193* | |
H55B | 0.5137 | 0.7928 | 0.111 | 0.193* | |
H55C | 0.6046 | 0.8488 | 0.156 | 0.193* | |
C45 | 0.9992 (3) | 0.5784 (3) | 0.4045 (2) | 0.0854 (14) | |
H45A | 1.0298 | 0.5683 | 0.3655 | 0.128* | |
H45B | 1.0059 | 0.5305 | 0.4348 | 0.128* | |
H45C | 1.0338 | 0.6233 | 0.434 | 0.128* | |
C74 | 1.0883 (3) | 0.5433 (3) | 0.2289 (3) | 0.111 (2) | |
H74A | 1.0936 | 0.4957 | 0.2594 | 0.166* | |
H74B | 1.1163 | 0.5896 | 0.2593 | 0.166* | |
H74C | 1.1265 | 0.5346 | 0.1941 | 0.166* | |
H103 | 0.463 (3) | 0.462 (2) | 0.1070 (19) | 0.068 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S92 | 0.0345 (4) | 0.0397 (4) | 0.0301 (3) | −0.0049 (3) | 0.0049 (3) | 0.0022 (3) |
Si91 | 0.0238 (3) | 0.0292 (4) | 0.0284 (3) | −0.0024 (3) | 0.0083 (3) | −0.0013 (3) |
O90 | 0.0280 (9) | 0.0350 (11) | 0.0296 (8) | −0.0014 (8) | 0.0121 (7) | 0.0008 (7) |
O88 | 0.0305 (10) | 0.0321 (11) | 0.0352 (9) | −0.0045 (8) | 0.0090 (7) | −0.0064 (8) |
O89 | 0.0234 (8) | 0.0391 (11) | 0.0280 (8) | −0.0024 (8) | 0.0098 (6) | −0.0033 (8) |
C60 | 0.0272 (13) | 0.0339 (15) | 0.0350 (13) | −0.0006 (11) | 0.0116 (10) | 0.0035 (11) |
N103 | 0.0425 (16) | 0.0503 (17) | 0.0577 (16) | −0.0083 (14) | 0.0229 (13) | 0.0003 (13) |
C65 | 0.0442 (17) | 0.0407 (18) | 0.0327 (13) | 0.0013 (13) | 0.0136 (12) | −0.0035 (12) |
C59 | 0.0252 (12) | 0.0303 (14) | 0.0274 (11) | 0.0033 (10) | 0.0088 (10) | 0.0039 (10) |
C67 | 0.0304 (14) | 0.0327 (15) | 0.0301 (12) | 0.0009 (11) | 0.0088 (10) | 0.0017 (11) |
C9 | 0.0436 (16) | 0.050 (2) | 0.0480 (16) | 0.0042 (14) | 0.0242 (13) | −0.0009 (14) |
C31 | 0.0349 (15) | 0.0390 (18) | 0.0507 (16) | 0.0001 (13) | 0.0055 (13) | −0.0147 (14) |
C95 | 0.055 (2) | 0.054 (2) | 0.086 (3) | −0.0008 (17) | 0.0250 (19) | 0.027 (2) |
C63 | 0.0484 (17) | 0.0496 (19) | 0.0388 (15) | 0.0060 (15) | 0.0231 (13) | −0.0003 (14) |
C2 | 0.0412 (16) | 0.0481 (19) | 0.0346 (14) | 0.0025 (14) | 0.0136 (12) | 0.0074 (13) |
C101 | 0.068 (2) | 0.066 (2) | 0.0533 (18) | 0.013 (2) | 0.0351 (17) | 0.0238 (18) |
C1 | 0.0335 (14) | 0.0379 (17) | 0.0336 (13) | −0.0034 (12) | 0.0173 (11) | 0.0010 (12) |
C80 | 0.056 (2) | 0.0379 (18) | 0.0607 (19) | −0.0035 (15) | 0.0257 (15) | 0.0043 (15) |
C78 | 0.0362 (15) | 0.0330 (16) | 0.0354 (14) | −0.0031 (12) | 0.0130 (11) | −0.0041 (12) |
C68 | 0.0375 (16) | 0.0379 (17) | 0.0590 (17) | −0.0057 (13) | 0.0235 (14) | −0.0034 (14) |
C10 | 0.0518 (18) | 0.048 (2) | 0.0412 (15) | 0.0150 (15) | 0.0137 (13) | 0.0125 (14) |
C61 | 0.0360 (15) | 0.0467 (19) | 0.0428 (15) | −0.0007 (13) | 0.0210 (12) | 0.0077 (13) |
C7 | 0.074 (2) | 0.080 (3) | 0.057 (2) | 0.004 (2) | 0.0427 (18) | −0.0133 (19) |
C3 | 0.064 (2) | 0.076 (3) | 0.0368 (16) | 0.0079 (19) | 0.0187 (15) | 0.0111 (16) |
C32 | 0.0370 (17) | 0.050 (2) | 0.070 (2) | −0.0043 (15) | 0.0056 (15) | −0.0230 (18) |
C93 | 0.0410 (19) | 0.062 (2) | 0.069 (2) | 0.0039 (16) | 0.0059 (16) | 0.0187 (18) |
C38 | 0.0486 (18) | 0.0331 (18) | 0.0504 (17) | −0.0022 (14) | 0.0135 (14) | −0.0071 (14) |
C30 | 0.0303 (14) | 0.0301 (15) | 0.0407 (14) | −0.0005 (11) | 0.0122 (11) | −0.0110 (12) |
C29 | 0.0447 (19) | 0.068 (3) | 0.094 (3) | 0.0049 (18) | 0.0227 (18) | −0.002 (2) |
C49 | 0.070 (2) | 0.0347 (18) | 0.0513 (18) | −0.0032 (16) | −0.0007 (16) | 0.0045 (15) |
C20 | 0.0417 (17) | 0.051 (2) | 0.067 (2) | 0.0078 (15) | 0.0300 (15) | −0.0019 (16) |
C39 | 0.048 (2) | 0.054 (2) | 0.0507 (18) | −0.0006 (16) | −0.0073 (15) | −0.0058 (16) |
C99 | 0.043 (2) | 0.112 (3) | 0.057 (2) | 0.019 (2) | 0.0176 (16) | 0.033 (2) |
C36 | 0.067 (2) | 0.0332 (19) | 0.072 (2) | −0.0102 (16) | 0.0221 (19) | −0.0042 (16) |
C16 | 0.095 (3) | 0.058 (3) | 0.080 (3) | −0.001 (2) | 0.037 (2) | 0.001 (2) |
C97 | 0.0373 (18) | 0.083 (3) | 0.080 (2) | −0.0064 (18) | 0.0221 (17) | 0.011 (2) |
C5 | 0.086 (3) | 0.098 (3) | 0.0397 (17) | 0.001 (2) | 0.0306 (18) | 0.002 (2) |
C84 | 0.0420 (18) | 0.049 (2) | 0.0521 (18) | −0.0120 (14) | 0.0104 (14) | −0.0110 (15) |
C22 | 0.057 (2) | 0.058 (3) | 0.120 (3) | 0.0098 (19) | 0.024 (2) | −0.003 (2) |
C34 | 0.050 (2) | 0.048 (2) | 0.088 (3) | −0.0214 (17) | 0.0250 (19) | −0.023 (2) |
C51 | 0.097 (4) | 0.238 (8) | 0.065 (3) | 0.008 (4) | 0.016 (3) | 0.039 (4) |
C70 | 0.180 (5) | 0.040 (2) | 0.095 (3) | −0.012 (3) | 0.084 (3) | −0.007 (2) |
C12 | 0.053 (3) | 0.092 (4) | 0.168 (5) | 0.012 (2) | 0.020 (3) | −0.041 (3) |
C41 | 0.074 (3) | 0.116 (4) | 0.080 (3) | 0.007 (3) | 0.028 (2) | 0.025 (3) |
C55 | 0.067 (3) | 0.184 (6) | 0.109 (4) | 0.050 (4) | −0.015 (3) | −0.040 (4) |
C45 | 0.071 (3) | 0.100 (4) | 0.069 (2) | 0.026 (2) | −0.005 (2) | 0.006 (2) |
C74 | 0.044 (2) | 0.109 (4) | 0.158 (5) | −0.006 (2) | −0.004 (3) | −0.077 (4) |
Geometric parameters (Å, º) top
S92—Si91 | 2.0261 (9) | C93—H93 | 0.93 |
Si91—O88 | 1.6473 (18) | C38—C36 | 1.391 (4) |
Si91—O89 | 1.6545 (18) | C38—C30 | 1.403 (4) |
Si91—O90 | 1.6558 (18) | C38—C49 | 1.527 (4) |
O90—C1 | 1.396 (3) | C29—C20 | 1.524 (5) |
O88—C30 | 1.387 (3) | C29—H29A | 0.96 |
O89—C59 | 1.388 (3) | C29—H29B | 0.96 |
C60—C61 | 1.397 (4) | C29—H29C | 0.96 |
C60—C59 | 1.400 (3) | C49—C51 | 1.504 (6) |
C60—C68 | 1.509 (4) | C49—C55 | 1.524 (6) |
N103—C101 | 1.311 (4) | C49—H49 | 0.98 |
N103—C93 | 1.317 (4) | C20—C22 | 1.522 (5) |
N103—H103 | 0.86 (4) | C20—H20 | 0.98 |
C65—C63 | 1.379 (4) | C39—C41 | 1.513 (5) |
C65—C67 | 1.393 (4) | C39—C45 | 1.516 (5) |
C65—H65 | 0.93 | C39—H39 | 0.98 |
C59—C67 | 1.405 (4) | C99—C97 | 1.357 (5) |
C67—C78 | 1.520 (4) | C99—H99 | 0.93 |
C9—C1 | 1.398 (4) | C36—C34 | 1.374 (5) |
C9—C7 | 1.411 (4) | C36—H36 | 0.93 |
C9—C20 | 1.509 (4) | C16—H16A | 0.96 |
C31—C32 | 1.387 (4) | C16—H16B | 0.96 |
C31—C30 | 1.402 (4) | C16—H16C | 0.96 |
C31—C39 | 1.513 (5) | C97—H97 | 0.93 |
C95—C97 | 1.359 (5) | C5—H5 | 0.93 |
C95—C93 | 1.365 (5) | C84—H84A | 0.96 |
C95—H95 | 0.93 | C84—H84B | 0.96 |
C63—C61 | 1.376 (4) | C84—H84C | 0.96 |
C63—H63 | 0.93 | C22—H22A | 0.96 |
C2—C1 | 1.399 (4) | C22—H22B | 0.96 |
C2—C3 | 1.399 (4) | C22—H22C | 0.96 |
C2—C10 | 1.505 (4) | C34—H34 | 0.93 |
C101—C99 | 1.366 (5) | C51—H51A | 0.96 |
C101—H101 | 0.93 | C51—H51B | 0.96 |
C80—C78 | 1.529 (4) | C51—H51C | 0.96 |
C80—H80A | 0.96 | C70—H70A | 0.96 |
C80—H80B | 0.96 | C70—H70B | 0.96 |
C80—H80C | 0.96 | C70—H70C | 0.96 |
C78—C84 | 1.525 (4) | C12—H12A | 0.96 |
C78—H78 | 0.98 | C12—H12B | 0.96 |
C68—C70 | 1.507 (5) | C12—H12C | 0.96 |
C68—C74 | 1.523 (5) | C41—H41A | 0.96 |
C68—H68 | 0.98 | C41—H41B | 0.96 |
C10—C12 | 1.507 (5) | C41—H41C | 0.96 |
C10—C16 | 1.527 (5) | C55—H55A | 0.96 |
C10—H10 | 0.98 | C55—H55B | 0.96 |
C61—H61 | 0.93 | C55—H55C | 0.96 |
C7—C5 | 1.372 (5) | C45—H45A | 0.96 |
C7—H7 | 0.93 | C45—H45B | 0.96 |
C3—C5 | 1.359 (5) | C45—H45C | 0.96 |
C3—H3 | 0.93 | C74—H74A | 0.96 |
C32—C34 | 1.370 (5) | C74—H74B | 0.96 |
C32—H32 | 0.93 | C74—H74C | 0.96 |
| | | |
O88—Si91—O89 | 106.77 (9) | H29B—C29—H29C | 109.5 |
O88—Si91—O90 | 102.30 (9) | C51—C49—C55 | 110.5 (4) |
O89—Si91—O90 | 105.54 (9) | C51—C49—C38 | 112.8 (4) |
O88—Si91—S92 | 116.65 (8) | C55—C49—C38 | 111.9 (3) |
O89—Si91—S92 | 113.36 (7) | C51—C49—H49 | 107.1 |
O90—Si91—S92 | 111.11 (7) | C55—C49—H49 | 107.1 |
C1—O90—Si91 | 131.10 (16) | C38—C49—H49 | 107.1 |
C30—O88—Si91 | 135.97 (16) | C9—C20—C22 | 112.0 (3) |
C59—O89—Si91 | 129.59 (15) | C9—C20—C29 | 112.0 (3) |
C61—C60—C59 | 117.8 (2) | C22—C20—C29 | 110.6 (3) |
C61—C60—C68 | 120.0 (2) | C9—C20—H20 | 107.3 |
C59—C60—C68 | 122.2 (2) | C22—C20—H20 | 107.3 |
C101—N103—C93 | 122.3 (3) | C29—C20—H20 | 107.3 |
C101—N103—H103 | 116 (2) | C41—C39—C31 | 110.9 (3) |
C93—N103—H103 | 122 (3) | C41—C39—C45 | 109.8 (3) |
C63—C65—C67 | 122.0 (3) | C31—C39—C45 | 113.6 (3) |
C63—C65—H65 | 119 | C41—C39—H39 | 107.4 |
C67—C65—H65 | 119 | C31—C39—H39 | 107.4 |
O89—C59—C60 | 117.6 (2) | C45—C39—H39 | 107.4 |
O89—C59—C67 | 120.8 (2) | C97—C99—C101 | 119.6 (3) |
C60—C59—C67 | 121.5 (2) | C97—C99—H99 | 120.2 |
C65—C67—C59 | 117.6 (2) | C101—C99—H99 | 120.2 |
C65—C67—C78 | 118.3 (2) | C34—C36—C38 | 121.8 (3) |
C59—C67—C78 | 123.9 (2) | C34—C36—H36 | 119.1 |
C1—C9—C7 | 116.7 (3) | C38—C36—H36 | 119.1 |
C1—C9—C20 | 122.8 (3) | C10—C16—H16A | 109.5 |
C7—C9—C20 | 120.5 (3) | C10—C16—H16B | 109.5 |
C32—C31—C30 | 117.4 (3) | H16A—C16—H16B | 109.5 |
C32—C31—C39 | 121.2 (3) | C10—C16—H16C | 109.5 |
C30—C31—C39 | 121.4 (3) | H16A—C16—H16C | 109.5 |
C97—C95—C93 | 119.2 (3) | H16B—C16—H16C | 109.5 |
C97—C95—H95 | 120.4 | C99—C97—C95 | 119.4 (3) |
C93—C95—H95 | 120.4 | C99—C97—H97 | 120.3 |
C61—C63—C65 | 119.0 (3) | C95—C97—H97 | 120.3 |
C61—C63—H63 | 120.5 | C3—C5—C7 | 120.2 (3) |
C65—C63—H63 | 120.5 | C3—C5—H5 | 119.9 |
C1—C2—C3 | 117.2 (3) | C7—C5—H5 | 119.9 |
C1—C2—C10 | 122.6 (2) | C78—C84—H84A | 109.5 |
C3—C2—C10 | 120.2 (3) | C78—C84—H84B | 109.5 |
N103—C101—C99 | 119.7 (3) | H84A—C84—H84B | 109.5 |
N103—C101—H101 | 120.2 | C78—C84—H84C | 109.5 |
C99—C101—H101 | 120.2 | H84A—C84—H84C | 109.5 |
O90—C1—C9 | 118.5 (2) | H84B—C84—H84C | 109.5 |
O90—C1—C2 | 118.7 (2) | C20—C22—H22A | 109.5 |
C9—C1—C2 | 122.6 (2) | C20—C22—H22B | 109.5 |
C78—C80—H80A | 109.5 | H22A—C22—H22B | 109.5 |
C78—C80—H80B | 109.5 | C20—C22—H22C | 109.5 |
H80A—C80—H80B | 109.5 | H22A—C22—H22C | 109.5 |
C78—C80—H80C | 109.5 | H22B—C22—H22C | 109.5 |
H80A—C80—H80C | 109.5 | C32—C34—C36 | 119.8 (3) |
H80B—C80—H80C | 109.5 | C32—C34—H34 | 120.1 |
C67—C78—C84 | 113.0 (2) | C36—C34—H34 | 120.1 |
C67—C78—C80 | 109.6 (2) | C49—C51—H51A | 109.5 |
C84—C78—C80 | 110.6 (3) | C49—C51—H51B | 109.5 |
C67—C78—H78 | 107.8 | H51A—C51—H51B | 109.5 |
C84—C78—H78 | 107.8 | C49—C51—H51C | 109.5 |
C80—C78—H78 | 107.8 | H51A—C51—H51C | 109.5 |
C70—C68—C60 | 111.7 (3) | H51B—C51—H51C | 109.5 |
C70—C68—C74 | 111.9 (4) | C68—C70—H70A | 109.5 |
C60—C68—C74 | 111.4 (3) | C68—C70—H70B | 109.5 |
C70—C68—H68 | 107.2 | H70A—C70—H70B | 109.5 |
C60—C68—H68 | 107.2 | C68—C70—H70C | 109.5 |
C74—C68—H68 | 107.2 | H70A—C70—H70C | 109.5 |
C2—C10—C12 | 114.1 (3) | H70B—C70—H70C | 109.5 |
C2—C10—C16 | 111.0 (3) | C10—C12—H12A | 109.5 |
C12—C10—C16 | 110.3 (3) | C10—C12—H12B | 109.5 |
C2—C10—H10 | 107 | H12A—C12—H12B | 109.5 |
C12—C10—H10 | 107 | C10—C12—H12C | 109.5 |
C16—C10—H10 | 107 | H12A—C12—H12C | 109.5 |
C63—C61—C60 | 121.9 (3) | H12B—C12—H12C | 109.5 |
C63—C61—H61 | 119 | C39—C41—H41A | 109.5 |
C60—C61—H61 | 119 | C39—C41—H41B | 109.5 |
C5—C7—C9 | 121.5 (3) | H41A—C41—H41B | 109.5 |
C5—C7—H7 | 119.3 | C39—C41—H41C | 109.5 |
C9—C7—H7 | 119.3 | H41A—C41—H41C | 109.5 |
C5—C3—C2 | 121.8 (3) | H41B—C41—H41C | 109.5 |
C5—C3—H3 | 119.1 | C49—C55—H55A | 109.5 |
C2—C3—H3 | 119.1 | C49—C55—H55B | 109.5 |
C34—C32—C31 | 121.7 (3) | H55A—C55—H55B | 109.5 |
C34—C32—H32 | 119.1 | C49—C55—H55C | 109.5 |
C31—C32—H32 | 119.1 | H55A—C55—H55C | 109.5 |
N103—C93—C95 | 119.9 (3) | H55B—C55—H55C | 109.5 |
N103—C93—H93 | 120.1 | C39—C45—H45A | 109.5 |
C95—C93—H93 | 120.1 | C39—C45—H45B | 109.5 |
C36—C38—C30 | 117.1 (3) | H45A—C45—H45B | 109.5 |
C36—C38—C49 | 120.2 (3) | C39—C45—H45C | 109.5 |
C30—C38—C49 | 122.7 (3) | H45A—C45—H45C | 109.5 |
O88—C30—C31 | 117.2 (3) | H45B—C45—H45C | 109.5 |
O88—C30—C38 | 120.5 (2) | C68—C74—H74A | 109.5 |
C31—C30—C38 | 122.1 (3) | C68—C74—H74B | 109.5 |
C20—C29—H29A | 109.5 | H74A—C74—H74B | 109.5 |
C20—C29—H29B | 109.5 | C68—C74—H74C | 109.5 |
H29A—C29—H29B | 109.5 | H74A—C74—H74C | 109.5 |
C20—C29—H29C | 109.5 | H74B—C74—H74C | 109.5 |
H29A—C29—H29C | 109.5 | | |
| | | |
O88—Si91—O90—C1 | −26.0 (2) | C3—C2—C10—C16 | 65.1 (4) |
O89—Si91—O90—C1 | 85.6 (2) | C65—C63—C61—C60 | −1.4 (4) |
S92—Si91—O90—C1 | −151.15 (19) | C59—C60—C61—C63 | −0.5 (4) |
O89—Si91—O88—C30 | 47.1 (3) | C68—C60—C61—C63 | 178.8 (3) |
O90—Si91—O88—C30 | 157.7 (2) | C1—C9—C7—C5 | 0.3 (5) |
S92—Si91—O88—C30 | −80.9 (2) | C20—C9—C7—C5 | 179.2 (3) |
O88—Si91—O89—C59 | −128.3 (2) | C1—C2—C3—C5 | 1.4 (5) |
O90—Si91—O89—C59 | 123.4 (2) | C10—C2—C3—C5 | −176.4 (4) |
S92—Si91—O89—C59 | 1.5 (2) | C30—C31—C32—C34 | 1.3 (5) |
Si91—O89—C59—C60 | 113.5 (2) | C39—C31—C32—C34 | −175.9 (3) |
Si91—O89—C59—C67 | −70.0 (3) | C101—N103—C93—C95 | −0.5 (6) |
C61—C60—C59—O89 | 179.2 (2) | C97—C95—C93—N103 | 1.5 (6) |
C68—C60—C59—O89 | −0.1 (4) | Si91—O88—C30—C31 | −101.0 (3) |
C61—C60—C59—C67 | 2.7 (4) | Si91—O88—C30—C38 | 82.8 (3) |
C68—C60—C59—C67 | −176.6 (2) | C32—C31—C30—O88 | −178.5 (2) |
C63—C65—C67—C59 | 1.1 (4) | C39—C31—C30—O88 | −1.3 (4) |
C63—C65—C67—C78 | −173.8 (3) | C32—C31—C30—C38 | −2.4 (4) |
O89—C59—C67—C65 | −179.4 (2) | C39—C31—C30—C38 | 174.8 (3) |
C60—C59—C67—C65 | −3.0 (4) | C36—C38—C30—O88 | 177.2 (3) |
O89—C59—C67—C78 | −4.8 (4) | C49—C38—C30—O88 | −0.3 (4) |
C60—C59—C67—C78 | 171.6 (2) | C36—C38—C30—C31 | 1.3 (4) |
C67—C65—C63—C61 | 1.1 (4) | C49—C38—C30—C31 | −176.3 (3) |
C93—N103—C101—C99 | −0.2 (5) | C36—C38—C49—C51 | 53.3 (5) |
Si91—O90—C1—C9 | 86.7 (3) | C30—C38—C49—C51 | −129.2 (4) |
Si91—O90—C1—C2 | −97.7 (3) | C36—C38—C49—C55 | −72.1 (5) |
C7—C9—C1—O90 | 177.7 (3) | C30—C38—C49—C55 | 105.4 (4) |
C20—C9—C1—O90 | −1.2 (4) | C1—C9—C20—C22 | −123.0 (4) |
C7—C9—C1—C2 | 2.2 (5) | C7—C9—C20—C22 | 58.2 (4) |
C20—C9—C1—C2 | −176.7 (3) | C1—C9—C20—C29 | 112.1 (3) |
C3—C2—C1—O90 | −178.5 (3) | C7—C9—C20—C29 | −66.7 (4) |
C10—C2—C1—O90 | −0.8 (4) | C32—C31—C39—C41 | 87.1 (4) |
C3—C2—C1—C9 | −3.0 (5) | C30—C31—C39—C41 | −90.0 (4) |
C10—C2—C1—C9 | 174.7 (3) | C32—C31—C39—C45 | −37.1 (4) |
C65—C67—C78—C84 | −55.4 (3) | C30—C31—C39—C45 | 145.7 (3) |
C59—C67—C78—C84 | 130.0 (3) | N103—C101—C99—C97 | −0.1 (6) |
C65—C67—C78—C80 | 68.4 (3) | C30—C38—C36—C34 | 1.0 (5) |
C59—C67—C78—C80 | −106.1 (3) | C49—C38—C36—C34 | 178.7 (3) |
C61—C60—C68—C70 | 67.9 (4) | C101—C99—C97—C95 | 1.0 (6) |
C59—C60—C68—C70 | −112.8 (3) | C93—C95—C97—C99 | −1.7 (6) |
C61—C60—C68—C74 | −58.1 (4) | C2—C3—C5—C7 | 0.9 (6) |
C59—C60—C68—C74 | 121.2 (4) | C9—C7—C5—C3 | −1.8 (6) |
C1—C2—C10—C12 | 122.1 (4) | C31—C32—C34—C36 | 0.9 (5) |
C3—C2—C10—C12 | −60.3 (5) | C38—C36—C34—C32 | −2.1 (6) |
C1—C2—C10—C16 | −112.5 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N103—H103···S92 | 0.86 (4) | 2.18 (4) | 3.026 (3) | 170 (3) |
Crystal data top
C36H51O3SSi·C5H6N | F(000) = 1456 |
Mr = 672.02 | Dx = 1.11 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10921 reflections |
a = 13.5221 (18) Å | θ = 1.6–29.3° |
b = 16.3924 (13) Å | µ = 0.15 mm−1 |
c = 18.982 (2) Å | T = 240 K |
β = 107.079 (10)° | Plate, colorless |
V = 4022.0 (8) Å3 | 0.38 × 0.31 × 0.15 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 4513 reflections with I > 2σ(I) |
Parabolic x-ray mirror monochromator | Rint = 0.063 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26°, θmin = 3.1° |
rotation method scans | h = −12→16 |
22221 measured reflections | k = −19→20 |
7876 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H 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 reflections | Δρmax = 0.33 e Å−3 |
440 parameters | Δρmin = −0.28 e Å−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 | x | y | z | Uiso*/Ueq | |
S92 | 0.59510 (5) | 0.52651 (5) | 0.09091 (3) | 0.04049 (18) | |
Si91 | 0.68647 (5) | 0.51657 (5) | 0.19639 (3) | 0.03007 (17) | |
O90 | 0.63149 (13) | 0.45864 (11) | 0.24571 (9) | 0.0345 (4) | |
O88 | 0.71034 (13) | 0.60122 (11) | 0.24506 (9) | 0.0363 (4) | |
O89 | 0.79959 (12) | 0.47364 (11) | 0.20351 (8) | 0.0336 (4) | |
C60 | 0.92631 (19) | 0.48725 (17) | 0.13961 (13) | 0.0354 (6) | |
N103 | 0.4062 (2) | 0.43817 (18) | 0.10533 (15) | 0.0556 (7) | |
C65 | 0.8459 (2) | 0.35254 (19) | 0.05347 (14) | 0.0438 (7) | |
H65 | 0.8193 | 0.3075 | 0.0242 | 0.053* | |
C59 | 0.84062 (18) | 0.44613 (16) | 0.14882 (13) | 0.0320 (6) | |
C67 | 0.79984 (19) | 0.37644 (16) | 0.10716 (13) | 0.0336 (6) | |
C9 | 0.5747 (2) | 0.5101 (2) | 0.34565 (16) | 0.0502 (7) | |
C31 | 0.8658 (2) | 0.66671 (19) | 0.31436 (17) | 0.0472 (7) | |
C95 | 0.3116 (3) | 0.3391 (2) | 0.1446 (2) | 0.0739 (11) | |
H95 | 0.3093 | 0.2951 | 0.175 | 0.089* | |
C63 | 0.9288 (2) | 0.3931 (2) | 0.04225 (15) | 0.0485 (7) | |
H63 | 0.9575 | 0.376 | 0.0058 | 0.058* | |
C2 | 0.7075 (2) | 0.4040 (2) | 0.36726 (15) | 0.0477 (7) | |
C101 | 0.3223 (3) | 0.4687 (2) | 0.06006 (19) | 0.0680 (10) | |
H101 | 0.3262 | 0.514 | 0.0315 | 0.082* | |
C1 | 0.6391 (2) | 0.45883 (17) | 0.32058 (13) | 0.0378 (6) | |
C80 | 0.7644 (3) | 0.2432 (2) | 0.15721 (19) | 0.0573 (8) | |
H80A | 0.7897 | 0.2128 | 0.1229 | 0.086* | |
H80B | 0.713 | 0.2116 | 0.1708 | 0.086* | |
H80C | 0.8206 | 0.255 | 0.2004 | 0.086* | |
C78 | 0.7162 (2) | 0.32307 (17) | 0.12141 (15) | 0.0398 (6) | |
H78 | 0.688 | 0.3516 | 0.1566 | 0.048* | |
C68 | 0.9748 (2) | 0.55942 (19) | 0.18699 (17) | 0.0474 (7) | |
H68 | 0.9374 | 0.5666 | 0.2236 | 0.057* | |
C10 | 0.7700 (2) | 0.3432 (2) | 0.33904 (16) | 0.0533 (8) | |
H10 | 0.7574 | 0.3542 | 0.2864 | 0.064* | |
C61 | 0.9691 (2) | 0.45975 (19) | 0.08580 (15) | 0.0444 (7) | |
H61 | 1.026 | 0.4868 | 0.0789 | 0.053* | |
C7 | 0.5827 (3) | 0.5066 (3) | 0.4213 (2) | 0.0747 (11) | |
H7 | 0.5407 | 0.5401 | 0.4398 | 0.09* | |
C3 | 0.7117 (3) | 0.4047 (3) | 0.44171 (17) | 0.0683 (10) | |
H3 | 0.7575 | 0.3697 | 0.474 | 0.082* | |
C32 | 0.9316 (3) | 0.7327 (2) | 0.3226 (2) | 0.0608 (9) | |
H32 | 0.9913 | 0.7337 | 0.3624 | 0.073* | |
C93 | 0.4034 (3) | 0.3746 (2) | 0.1473 (2) | 0.0687 (10) | |
H93 | 0.4645 | 0.3539 | 0.1788 | 0.082* | |
C38 | 0.7543 (2) | 0.73151 (19) | 0.20240 (17) | 0.0489 (7) | |
C30 | 0.7775 (2) | 0.66640 (17) | 0.25219 (15) | 0.0378 (6) | |
C29 | 0.3862 (3) | 0.5409 (3) | 0.2865 (3) | 0.0813 (12) | |
H29A | 0.3762 | 0.4855 | 0.2693 | 0.122* | |
H29B | 0.3394 | 0.5759 | 0.2517 | 0.122* | |
H29C | 0.373 | 0.5448 | 0.3334 | 0.122* | |
C49 | 0.6557 (3) | 0.7344 (2) | 0.13723 (17) | 0.0602 (9) | |
H49 | 0.6242 | 0.6801 | 0.1329 | 0.072* | |
C20 | 0.4974 (2) | 0.5667 (2) | 0.29460 (19) | 0.0575 (8) | |
H20 | 0.508 | 0.563 | 0.2458 | 0.069* | |
C39 | 0.8849 (3) | 0.5994 (2) | 0.37117 (18) | 0.0621 (10) | |
H39 | 0.8498 | 0.5504 | 0.3465 | 0.075* | |
C99 | 0.2282 (3) | 0.4336 (3) | 0.0547 (2) | 0.0803 (13) | |
H99 | 0.1682 | 0.4545 | 0.0221 | 0.096* | |
C36 | 0.8243 (3) | 0.7959 (2) | 0.2149 (2) | 0.0654 (10) | |
H36 | 0.8115 | 0.8397 | 0.1823 | 0.078* | |
C16 | 0.7336 (4) | 0.2559 (3) | 0.3459 (2) | 0.0894 (13) | |
H16A | 0.7451 | 0.2429 | 0.397 | 0.134* | |
H16B | 0.7717 | 0.2187 | 0.3248 | 0.134* | |
H16C | 0.6612 | 0.2515 | 0.3203 | 0.134* | |
C97 | 0.2237 (3) | 0.3687 (3) | 0.0972 (2) | 0.0726 (11) | |
H97 | 0.1604 | 0.3443 | 0.0939 | 0.087* | |
C5 | 0.6511 (3) | 0.4549 (3) | 0.46841 (19) | 0.0799 (12) | |
H5 | 0.656 | 0.4542 | 0.5183 | 0.096* | |
C84 | 0.6266 (2) | 0.3059 (2) | 0.05202 (17) | 0.0556 (8) | |
H84A | 0.5971 | 0.3566 | 0.0304 | 0.083* | |
H84B | 0.5747 | 0.2742 | 0.0649 | 0.083* | |
H84C | 0.6519 | 0.2761 | 0.0173 | 0.083* | |
C22 | 0.5144 (3) | 0.6550 (3) | 0.3193 (3) | 0.0905 (14) | |
H22A | 0.5007 | 0.6612 | 0.3659 | 0.136* | |
H22B | 0.4685 | 0.6894 | 0.2833 | 0.136* | |
H22C | 0.5847 | 0.6701 | 0.3244 | 0.136* | |
C34 | 0.9120 (3) | 0.7966 (2) | 0.2742 (2) | 0.0701 (11) | |
H34 | 0.9577 | 0.8403 | 0.2814 | 0.084* | |
C51 | 0.6761 (5) | 0.7524 (5) | 0.0654 (3) | 0.147 (3) | |
H51A | 0.7068 | 0.8055 | 0.0675 | 0.221* | |
H51B | 0.6121 | 0.7511 | 0.0263 | 0.221* | |
H51C | 0.7224 | 0.7122 | 0.0562 | 0.221* | |
C70 | 0.9617 (5) | 0.6369 (3) | 0.1430 (3) | 0.1106 (19) | |
H70A | 0.9995 | 0.633 | 0.1075 | 0.166* | |
H70B | 0.9876 | 0.682 | 0.1754 | 0.166* | |
H70C | 0.8897 | 0.6453 | 0.1179 | 0.166* | |
C12 | 0.8846 (3) | 0.3505 (3) | 0.3748 (4) | 0.123 (2) | |
H12A | 0.9077 | 0.4033 | 0.3645 | 0.185* | |
H12B | 0.9198 | 0.309 | 0.3556 | 0.185* | |
H12C | 0.8995 | 0.3437 | 0.4271 | 0.185* | |
C41 | 0.8377 (4) | 0.6209 (4) | 0.4319 (2) | 0.0999 (15) | |
H41A | 0.8735 | 0.6669 | 0.4591 | 0.15* | |
H41B | 0.8437 | 0.5752 | 0.4644 | 0.15* | |
H41C | 0.766 | 0.6344 | 0.4106 | 0.15* | |
C55 | 0.5776 (4) | 0.7942 (4) | 0.1506 (3) | 0.144 (3) | |
H55A | 0.5596 | 0.7783 | 0.1939 | 0.216* | |
H55B | 0.5166 | 0.7941 | 0.1089 | 0.216* | |
H55C | 0.607 | 0.8479 | 0.1574 | 0.216* | |
C45 | 0.9986 (3) | 0.5785 (3) | 0.4041 (2) | 0.0965 (16) | |
H45A | 1.0287 | 0.5674 | 0.3652 | 0.145* | |
H45B | 1.0051 | 0.5312 | 0.435 | 0.145* | |
H45C | 1.0338 | 0.6236 | 0.4329 | 0.145* | |
C74 | 1.0871 (3) | 0.5424 (3) | 0.2292 (3) | 0.127 (2) | |
H74A | 1.0908 | 0.4955 | 0.2602 | 0.191* | |
H74B | 1.1157 | 0.5888 | 0.2592 | 0.191* | |
H74C | 1.1258 | 0.5322 | 0.1951 | 0.191* | |
H103 | 0.472 (3) | 0.459 (2) | 0.103 (2) | 0.086 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S92 | 0.0383 (4) | 0.0460 (4) | 0.0333 (3) | −0.0057 (3) | 0.0046 (3) | 0.0028 (3) |
Si91 | 0.0260 (3) | 0.0334 (4) | 0.0309 (3) | −0.0021 (3) | 0.0086 (3) | −0.0014 (3) |
O90 | 0.0332 (9) | 0.0392 (11) | 0.0330 (8) | −0.0012 (8) | 0.0128 (7) | 0.0009 (7) |
O88 | 0.0330 (9) | 0.0374 (11) | 0.0376 (9) | −0.0040 (8) | 0.0090 (7) | −0.0064 (8) |
O89 | 0.0285 (8) | 0.0420 (11) | 0.0314 (8) | −0.0007 (8) | 0.0107 (7) | −0.0032 (8) |
C60 | 0.0326 (13) | 0.0379 (15) | 0.0372 (13) | 0.0019 (11) | 0.0127 (10) | 0.0054 (11) |
N103 | 0.0469 (16) | 0.0589 (18) | 0.0662 (17) | −0.0108 (14) | 0.0247 (14) | −0.0008 (14) |
C65 | 0.0487 (16) | 0.0482 (18) | 0.0359 (14) | 0.0022 (13) | 0.0145 (12) | −0.0046 (12) |
C59 | 0.0275 (12) | 0.0370 (15) | 0.0315 (12) | 0.0042 (10) | 0.0086 (10) | 0.0031 (10) |
C67 | 0.0338 (13) | 0.0352 (15) | 0.0323 (12) | 0.0002 (11) | 0.0102 (10) | 0.0016 (11) |
C9 | 0.0493 (17) | 0.055 (2) | 0.0539 (16) | 0.0010 (15) | 0.0275 (14) | −0.0024 (15) |
C31 | 0.0366 (15) | 0.0458 (18) | 0.0553 (17) | 0.0001 (13) | 0.0077 (13) | −0.0163 (14) |
C95 | 0.066 (2) | 0.064 (3) | 0.095 (3) | −0.0009 (19) | 0.029 (2) | 0.033 (2) |
C63 | 0.0526 (17) | 0.061 (2) | 0.0401 (14) | 0.0065 (15) | 0.0265 (13) | 0.0025 (14) |
C2 | 0.0491 (17) | 0.059 (2) | 0.0365 (14) | 0.0023 (14) | 0.0145 (12) | 0.0062 (13) |
C101 | 0.076 (2) | 0.078 (3) | 0.061 (2) | 0.016 (2) | 0.0375 (18) | 0.0287 (19) |
C1 | 0.0364 (14) | 0.0467 (17) | 0.0346 (13) | −0.0008 (12) | 0.0173 (11) | 0.0002 (11) |
C80 | 0.063 (2) | 0.045 (2) | 0.069 (2) | −0.0036 (16) | 0.0278 (16) | 0.0087 (16) |
C78 | 0.0389 (14) | 0.0375 (16) | 0.0431 (14) | −0.0058 (12) | 0.0123 (12) | −0.0036 (12) |
C68 | 0.0421 (16) | 0.0432 (18) | 0.0635 (18) | −0.0096 (13) | 0.0255 (14) | −0.0069 (14) |
C10 | 0.0585 (19) | 0.058 (2) | 0.0450 (16) | 0.0169 (16) | 0.0170 (14) | 0.0150 (15) |
C61 | 0.0404 (15) | 0.0520 (19) | 0.0480 (15) | −0.0009 (13) | 0.0240 (12) | 0.0061 (13) |
C7 | 0.086 (3) | 0.092 (3) | 0.064 (2) | 0.008 (2) | 0.050 (2) | −0.011 (2) |
C3 | 0.079 (2) | 0.088 (3) | 0.0383 (16) | 0.008 (2) | 0.0176 (16) | 0.0105 (17) |
C32 | 0.0442 (18) | 0.054 (2) | 0.077 (2) | −0.0059 (15) | 0.0072 (16) | −0.0269 (19) |
C93 | 0.0464 (19) | 0.072 (3) | 0.079 (2) | −0.0011 (17) | 0.0054 (17) | 0.022 (2) |
C38 | 0.0533 (18) | 0.0368 (18) | 0.0564 (18) | −0.0044 (14) | 0.0159 (14) | −0.0082 (14) |
C30 | 0.0348 (14) | 0.0319 (15) | 0.0476 (15) | 0.0006 (11) | 0.0135 (11) | −0.0107 (12) |
C29 | 0.052 (2) | 0.077 (3) | 0.117 (3) | 0.0024 (19) | 0.030 (2) | −0.005 (2) |
C49 | 0.076 (2) | 0.0403 (19) | 0.0524 (18) | −0.0035 (16) | −0.0003 (16) | 0.0038 (14) |
C20 | 0.0505 (18) | 0.056 (2) | 0.075 (2) | 0.0093 (16) | 0.0327 (16) | −0.0047 (17) |
C39 | 0.055 (2) | 0.059 (2) | 0.0566 (19) | −0.0031 (16) | −0.0077 (16) | −0.0068 (16) |
C99 | 0.047 (2) | 0.127 (4) | 0.068 (2) | 0.021 (2) | 0.0182 (17) | 0.032 (2) |
C36 | 0.077 (2) | 0.039 (2) | 0.082 (2) | −0.0105 (17) | 0.026 (2) | −0.0032 (17) |
C16 | 0.120 (4) | 0.068 (3) | 0.087 (3) | −0.007 (3) | 0.040 (3) | −0.002 (2) |
C97 | 0.0431 (18) | 0.091 (3) | 0.088 (3) | −0.0078 (19) | 0.0261 (18) | 0.010 (2) |
C5 | 0.098 (3) | 0.106 (4) | 0.0430 (18) | 0.009 (3) | 0.0328 (19) | 0.003 (2) |
C84 | 0.0471 (18) | 0.058 (2) | 0.0584 (18) | −0.0169 (15) | 0.0100 (15) | −0.0124 (15) |
C22 | 0.064 (2) | 0.061 (3) | 0.144 (4) | 0.006 (2) | 0.027 (3) | −0.006 (3) |
C34 | 0.061 (2) | 0.054 (2) | 0.097 (3) | −0.0232 (18) | 0.025 (2) | −0.026 (2) |
C51 | 0.115 (4) | 0.249 (9) | 0.071 (3) | 0.008 (5) | 0.015 (3) | 0.043 (4) |
C70 | 0.209 (6) | 0.046 (2) | 0.107 (3) | −0.014 (3) | 0.093 (4) | −0.009 (2) |
C12 | 0.060 (3) | 0.110 (4) | 0.190 (6) | 0.020 (3) | 0.021 (3) | −0.045 (4) |
C41 | 0.083 (3) | 0.132 (5) | 0.087 (3) | 0.007 (3) | 0.029 (2) | 0.028 (3) |
C55 | 0.080 (3) | 0.202 (7) | 0.121 (4) | 0.052 (4) | −0.016 (3) | −0.040 (4) |
C45 | 0.075 (3) | 0.119 (4) | 0.077 (3) | 0.027 (3) | −0.007 (2) | 0.009 (3) |
C74 | 0.051 (2) | 0.125 (5) | 0.177 (5) | −0.007 (3) | −0.010 (3) | −0.089 (4) |
Geometric parameters (Å, º) top
S92—Si91 | 2.0271 (9) | C93—H93 | 0.93 |
Si91—O88 | 1.6457 (18) | C38—C36 | 1.392 (5) |
Si91—O89 | 1.6528 (18) | C38—C30 | 1.399 (4) |
Si91—O90 | 1.6552 (18) | C38—C49 | 1.530 (4) |
O90—C1 | 1.394 (3) | C29—C20 | 1.526 (5) |
O88—C30 | 1.382 (3) | C29—H29A | 0.96 |
O89—C59 | 1.388 (3) | C29—H29B | 0.96 |
C60—C61 | 1.388 (4) | C29—H29C | 0.96 |
C60—C59 | 1.395 (4) | C49—C51 | 1.498 (6) |
C60—C68 | 1.514 (4) | C49—C55 | 1.516 (6) |
N103—C101 | 1.305 (4) | C49—H49 | 0.98 |
N103—C93 | 1.319 (4) | C20—C22 | 1.517 (5) |
N103—H103 | 0.96 (4) | C20—H20 | 0.98 |
C65—C63 | 1.374 (4) | C39—C41 | 1.514 (6) |
C65—C67 | 1.397 (4) | C39—C45 | 1.519 (5) |
C65—H65 | 0.93 | C39—H39 | 0.98 |
C59—C67 | 1.407 (4) | C99—C97 | 1.348 (5) |
C67—C78 | 1.516 (4) | C99—H99 | 0.93 |
C9—C1 | 1.392 (4) | C36—C34 | 1.374 (5) |
C9—C7 | 1.409 (4) | C36—H36 | 0.93 |
C9—C20 | 1.516 (4) | C16—H16A | 0.96 |
C31—C32 | 1.380 (5) | C16—H16B | 0.96 |
C31—C30 | 1.411 (4) | C16—H16C | 0.96 |
C31—C39 | 1.511 (5) | C97—H97 | 0.93 |
C95—C97 | 1.353 (5) | C5—H5 | 0.93 |
C95—C93 | 1.357 (5) | C84—H84A | 0.96 |
C95—H95 | 0.93 | C84—H84B | 0.96 |
C63—C61 | 1.381 (4) | C84—H84C | 0.96 |
C63—H63 | 0.93 | C22—H22A | 0.96 |
C2—C3 | 1.398 (4) | C22—H22B | 0.96 |
C2—C1 | 1.403 (4) | C22—H22C | 0.96 |
C2—C10 | 1.504 (4) | C34—H34 | 0.93 |
C101—C99 | 1.371 (5) | C51—H51A | 0.96 |
C101—H101 | 0.93 | C51—H51B | 0.96 |
C80—C78 | 1.530 (4) | C51—H51C | 0.96 |
C80—H80A | 0.96 | C70—H70A | 0.96 |
C80—H80B | 0.96 | C70—H70B | 0.96 |
C80—H80C | 0.96 | C70—H70C | 0.96 |
C78—C84 | 1.531 (4) | C12—H12A | 0.96 |
C78—H78 | 0.98 | C12—H12B | 0.96 |
C68—C70 | 1.502 (5) | C12—H12C | 0.96 |
C68—C74 | 1.521 (5) | C41—H41A | 0.96 |
C68—H68 | 0.98 | C41—H41B | 0.96 |
C10—C12 | 1.502 (5) | C41—H41C | 0.96 |
C10—C16 | 1.531 (5) | C55—H55A | 0.96 |
C10—H10 | 0.98 | C55—H55B | 0.96 |
C61—H61 | 0.93 | C55—H55C | 0.96 |
C7—C5 | 1.374 (5) | C45—H45A | 0.96 |
C7—H7 | 0.93 | C45—H45B | 0.96 |
C3—C5 | 1.360 (5) | C45—H45C | 0.96 |
C3—H3 | 0.93 | C74—H74A | 0.96 |
C32—C34 | 1.367 (5) | C74—H74B | 0.96 |
C32—H32 | 0.93 | C74—H74C | 0.96 |
| | | |
O88—Si91—O89 | 106.79 (9) | H29B—C29—H29C | 109.5 |
O88—Si91—O90 | 102.29 (9) | C51—C49—C55 | 110.4 (4) |
O89—Si91—O90 | 105.55 (9) | C51—C49—C38 | 113.1 (4) |
O88—Si91—S92 | 116.67 (7) | C55—C49—C38 | 111.7 (3) |
O89—Si91—S92 | 113.32 (7) | C51—C49—H49 | 107.1 |
O90—Si91—S92 | 111.11 (7) | C55—C49—H49 | 107.1 |
C1—O90—Si91 | 131.61 (16) | C38—C49—H49 | 107.1 |
C30—O88—Si91 | 136.18 (17) | C9—C20—C22 | 111.9 (3) |
C59—O89—Si91 | 129.85 (14) | C9—C20—C29 | 111.6 (3) |
C61—C60—C59 | 118.4 (3) | C22—C20—C29 | 110.6 (3) |
C61—C60—C68 | 119.3 (2) | C9—C20—H20 | 107.5 |
C59—C60—C68 | 122.3 (2) | C22—C20—H20 | 107.5 |
C101—N103—C93 | 121.7 (3) | C29—C20—H20 | 107.5 |
C101—N103—H103 | 118 (2) | C31—C39—C41 | 110.6 (3) |
C93—N103—H103 | 120 (2) | C31—C39—C45 | 113.5 (3) |
C63—C65—C67 | 122.4 (3) | C41—C39—C45 | 110.0 (3) |
C63—C65—H65 | 118.8 | C31—C39—H39 | 107.5 |
C67—C65—H65 | 118.8 | C41—C39—H39 | 107.5 |
O89—C59—C60 | 117.8 (2) | C45—C39—H39 | 107.5 |
O89—C59—C67 | 120.5 (2) | C97—C99—C101 | 119.4 (3) |
C60—C59—C67 | 121.7 (2) | C97—C99—H99 | 120.3 |
C65—C67—C59 | 116.9 (2) | C101—C99—H99 | 120.3 |
C65—C67—C78 | 118.9 (2) | C34—C36—C38 | 121.7 (4) |
C59—C67—C78 | 123.9 (2) | C34—C36—H36 | 119.1 |
C1—C9—C7 | 117.1 (3) | C38—C36—H36 | 119.1 |
C1—C9—C20 | 122.3 (3) | C10—C16—H16A | 109.5 |
C7—C9—C20 | 120.6 (3) | C10—C16—H16B | 109.5 |
C32—C31—C30 | 117.2 (3) | H16A—C16—H16B | 109.5 |
C32—C31—C39 | 121.5 (3) | C10—C16—H16C | 109.5 |
C30—C31—C39 | 121.3 (3) | H16A—C16—H16C | 109.5 |
C97—C95—C93 | 119.1 (3) | H16B—C16—H16C | 109.5 |
C97—C95—H95 | 120.4 | C99—C97—C95 | 119.7 (4) |
C93—C95—H95 | 120.4 | C99—C97—H97 | 120.2 |
C65—C63—C61 | 119.1 (3) | C95—C97—H97 | 120.2 |
C65—C63—H63 | 120.5 | C3—C5—C7 | 119.7 (3) |
C61—C63—H63 | 120.5 | C3—C5—H5 | 120.2 |
C3—C2—C1 | 117.2 (3) | C7—C5—H5 | 120.2 |
C3—C2—C10 | 120.4 (3) | C78—C84—H84A | 109.5 |
C1—C2—C10 | 122.4 (2) | C78—C84—H84B | 109.5 |
N103—C101—C99 | 119.8 (3) | H84A—C84—H84B | 109.5 |
N103—C101—H101 | 120.1 | C78—C84—H84C | 109.5 |
C99—C101—H101 | 120.1 | H84A—C84—H84C | 109.5 |
C9—C1—O90 | 118.9 (2) | H84B—C84—H84C | 109.5 |
C9—C1—C2 | 122.3 (3) | C20—C22—H22A | 109.5 |
O90—C1—C2 | 118.7 (2) | C20—C22—H22B | 109.5 |
C78—C80—H80A | 109.5 | H22A—C22—H22B | 109.5 |
C78—C80—H80B | 109.5 | C20—C22—H22C | 109.5 |
H80A—C80—H80B | 109.5 | H22A—C22—H22C | 109.5 |
C78—C80—H80C | 109.5 | H22B—C22—H22C | 109.5 |
H80A—C80—H80C | 109.5 | C32—C34—C36 | 119.7 (3) |
H80B—C80—H80C | 109.5 | C32—C34—H34 | 120.2 |
C67—C78—C80 | 109.3 (2) | C36—C34—H34 | 120.2 |
C67—C78—C84 | 113.3 (2) | C49—C51—H51A | 109.5 |
C80—C78—C84 | 110.5 (3) | C49—C51—H51B | 109.5 |
C67—C78—H78 | 107.8 | H51A—C51—H51B | 109.5 |
C80—C78—H78 | 107.8 | C49—C51—H51C | 109.5 |
C84—C78—H78 | 107.8 | H51A—C51—H51C | 109.5 |
C70—C68—C60 | 111.8 (3) | H51B—C51—H51C | 109.5 |
C70—C68—C74 | 112.6 (4) | C68—C70—H70A | 109.5 |
C60—C68—C74 | 111.2 (3) | C68—C70—H70B | 109.5 |
C70—C68—H68 | 107 | H70A—C70—H70B | 109.5 |
C60—C68—H68 | 107 | C68—C70—H70C | 109.5 |
C74—C68—H68 | 107 | H70A—C70—H70C | 109.5 |
C12—C10—C2 | 113.6 (3) | H70B—C70—H70C | 109.5 |
C12—C10—C16 | 110.5 (3) | C10—C12—H12A | 109.5 |
C2—C10—C16 | 111.1 (3) | C10—C12—H12B | 109.5 |
C12—C10—H10 | 107.1 | H12A—C12—H12B | 109.5 |
C2—C10—H10 | 107.1 | C10—C12—H12C | 109.5 |
C16—C10—H10 | 107.1 | H12A—C12—H12C | 109.5 |
C63—C61—C60 | 121.4 (3) | H12B—C12—H12C | 109.5 |
C63—C61—H61 | 119.3 | C39—C41—H41A | 109.5 |
C60—C61—H61 | 119.3 | C39—C41—H41B | 109.5 |
C5—C7—C9 | 121.6 (3) | H41A—C41—H41B | 109.5 |
C5—C7—H7 | 119.2 | C39—C41—H41C | 109.5 |
C9—C7—H7 | 119.2 | H41A—C41—H41C | 109.5 |
C5—C3—C2 | 122.1 (3) | H41B—C41—H41C | 109.5 |
C5—C3—H3 | 118.9 | C49—C55—H55A | 109.5 |
C2—C3—H3 | 118.9 | C49—C55—H55B | 109.5 |
C34—C32—C31 | 122.2 (3) | H55A—C55—H55B | 109.5 |
C34—C32—H32 | 118.9 | C49—C55—H55C | 109.5 |
C31—C32—H32 | 118.9 | H55A—C55—H55C | 109.5 |
N103—C93—C95 | 120.3 (3) | H55B—C55—H55C | 109.5 |
N103—C93—H93 | 119.9 | C39—C45—H45A | 109.5 |
C95—C93—H93 | 119.9 | C39—C45—H45B | 109.5 |
C36—C38—C30 | 117.2 (3) | H45A—C45—H45B | 109.5 |
C36—C38—C49 | 120.1 (3) | C39—C45—H45C | 109.5 |
C30—C38—C49 | 122.6 (3) | H45A—C45—H45C | 109.5 |
O88—C30—C38 | 120.9 (2) | H45B—C45—H45C | 109.5 |
O88—C30—C31 | 117.0 (3) | C68—C74—H74A | 109.5 |
C38—C30—C31 | 121.9 (3) | C68—C74—H74B | 109.5 |
C20—C29—H29A | 109.5 | H74A—C74—H74B | 109.5 |
C20—C29—H29B | 109.5 | C68—C74—H74C | 109.5 |
H29A—C29—H29B | 109.5 | H74A—C74—H74C | 109.5 |
C20—C29—H29C | 109.5 | H74B—C74—H74C | 109.5 |
H29A—C29—H29C | 109.5 | | |
| | | |
O88—Si91—O90—C1 | −25.5 (2) | C1—C2—C10—C16 | −111.7 (3) |
O89—Si91—O90—C1 | 86.0 (2) | C65—C63—C61—C60 | −1.1 (4) |
S92—Si91—O90—C1 | −150.8 (2) | C59—C60—C61—C63 | −0.3 (4) |
O89—Si91—O88—C30 | 46.9 (3) | C68—C60—C61—C63 | 178.7 (3) |
O90—Si91—O88—C30 | 157.6 (2) | C1—C9—C7—C5 | 0.0 (6) |
S92—Si91—O88—C30 | −81.0 (2) | C20—C9—C7—C5 | 179.0 (4) |
O88—Si91—O89—C59 | −128.1 (2) | C1—C2—C3—C5 | 1.3 (6) |
O90—Si91—O89—C59 | 123.6 (2) | C10—C2—C3—C5 | −175.4 (4) |
S92—Si91—O89—C59 | 1.8 (2) | C30—C31—C32—C34 | 1.7 (5) |
Si91—O89—C59—C60 | 113.3 (2) | C39—C31—C32—C34 | −175.7 (3) |
Si91—O89—C59—C67 | −70.0 (3) | C101—N103—C93—C95 | −0.4 (6) |
C61—C60—C59—O89 | 179.1 (2) | C97—C95—C93—N103 | 1.6 (7) |
C68—C60—C59—O89 | 0.2 (4) | Si91—O88—C30—C38 | 82.8 (3) |
C61—C60—C59—C67 | 2.5 (4) | Si91—O88—C30—C31 | −101.5 (3) |
C68—C60—C59—C67 | −176.5 (2) | C36—C38—C30—O88 | 177.9 (3) |
C63—C65—C67—C59 | 1.6 (4) | C49—C38—C30—O88 | −0.9 (4) |
C63—C65—C67—C78 | −173.5 (3) | C36—C38—C30—C31 | 2.5 (5) |
O89—C59—C67—C65 | −179.7 (2) | C49—C38—C30—C31 | −176.4 (3) |
C60—C59—C67—C65 | −3.1 (4) | C32—C31—C30—O88 | −178.5 (3) |
O89—C59—C67—C78 | −4.8 (4) | C39—C31—C30—O88 | −1.0 (4) |
C60—C59—C67—C78 | 171.8 (2) | C32—C31—C30—C38 | −2.8 (4) |
C67—C65—C63—C61 | 0.4 (4) | C39—C31—C30—C38 | 174.6 (3) |
C93—N103—C101—C99 | −0.8 (6) | C36—C38—C49—C51 | 52.0 (5) |
C7—C9—C1—O90 | 178.1 (3) | C30—C38—C49—C51 | −129.2 (4) |
C20—C9—C1—O90 | −0.9 (4) | C36—C38—C49—C55 | −73.3 (5) |
C7—C9—C1—C2 | 1.8 (5) | C30—C38—C49—C55 | 105.6 (5) |
C20—C9—C1—C2 | −177.2 (3) | C1—C9—C20—C22 | −123.2 (4) |
Si91—O90—C1—C9 | 86.2 (3) | C7—C9—C20—C22 | 57.9 (5) |
Si91—O90—C1—C2 | −97.3 (3) | C1—C9—C20—C29 | 112.3 (4) |
C3—C2—C1—C9 | −2.4 (5) | C7—C9—C20—C29 | −66.7 (4) |
C10—C2—C1—C9 | 174.2 (3) | C32—C31—C39—C41 | 86.4 (4) |
C3—C2—C1—O90 | −178.8 (3) | C30—C31—C39—C41 | −90.9 (4) |
C10—C2—C1—O90 | −2.1 (4) | C32—C31—C39—C45 | −37.7 (5) |
C65—C67—C78—C80 | 68.8 (3) | C30—C31—C39—C45 | 145.0 (3) |
C59—C67—C78—C80 | −106.0 (3) | N103—C101—C99—C97 | 0.9 (6) |
C65—C67—C78—C84 | −54.9 (3) | C30—C38—C36—C34 | −1.0 (5) |
C59—C67—C78—C84 | 130.3 (3) | C49—C38—C36—C34 | 177.9 (4) |
C61—C60—C68—C70 | 67.5 (4) | C101—C99—C97—C95 | 0.3 (7) |
C59—C60—C68—C70 | −113.5 (4) | C93—C95—C97—C99 | −1.5 (7) |
C61—C60—C68—C74 | −59.3 (4) | C2—C3—C5—C7 | 0.4 (7) |
C59—C60—C68—C74 | 119.7 (4) | C9—C7—C5—C3 | −1.1 (7) |
C3—C2—C10—C12 | −60.5 (5) | C31—C32—C34—C36 | −0.3 (6) |
C1—C2—C10—C12 | 123.0 (4) | C38—C36—C34—C32 | −0.1 (6) |
C3—C2—C10—C16 | 64.9 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N103—H103···S92 | 0.96 (4) | 2.07 (4) | 3.017 (3) | 167 (3) |
Crystal data top
C36H51O3SSi·C5H6N | F(000) = 1456 |
Mr = 672.02 | Dx = 1.103 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9082 reflections |
a = 13.5393 (17) Å | θ = 3.0–29.3° |
b = 16.4475 (16) Å | µ = 0.15 mm−1 |
c = 19.021 (2) Å | T = 270 K |
β = 107.159 (9)° | Plate, colorless |
V = 4047.2 (8) Å3 | 0.38 × 0.31 × 0.15 mm |
Z = 4 | |
Data collection top
STOE IPDS 2T diffractometer | 3787 reflections with I > 2u(I) |
Parabolic x-ray mirror monochromator | Rint = 0.071 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.7° |
rotation method scans | h = −16→13 |
23099 measured reflections | k = −19→20 |
7927 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H 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 reflections | Δρmax = 0.22 e Å−3 |
440 parameters | Δρmin = −0.29 e Å−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 | x | y | z | Uiso*/Ueq | |
C1 | 0.6392 (2) | 0.45978 (19) | 0.32092 (14) | 0.0465 (7) | |
C2 | 0.7078 (3) | 0.4049 (2) | 0.36738 (16) | 0.0571 (9) | |
C3 | 0.7109 (3) | 0.4057 (3) | 0.44165 (19) | 0.0812 (12) | |
H3 | 0.7555 | 0.3701 | 0.474 | 0.097* | |
C5 | 0.6513 (4) | 0.4563 (3) | 0.4681 (2) | 0.0963 (15) | |
H5 | 0.6563 | 0.456 | 0.5179 | 0.116* | |
C7 | 0.5836 (3) | 0.5079 (3) | 0.4211 (2) | 0.0844 (12) | |
H7 | 0.542 | 0.5415 | 0.4396 | 0.101* | |
C9 | 0.5751 (3) | 0.5114 (2) | 0.34554 (17) | 0.0592 (9) | |
C10 | 0.7702 (3) | 0.3442 (2) | 0.33953 (18) | 0.0641 (10) | |
H10 | 0.7577 | 0.3551 | 0.287 | 0.077* | |
C12 | 0.8849 (4) | 0.3506 (4) | 0.3753 (4) | 0.138 (2) | |
H12A | 0.9073 | 0.405 | 0.3697 | 0.207* | |
H12B | 0.9201 | 0.3131 | 0.3523 | 0.207* | |
H12C | 0.9006 | 0.3379 | 0.4267 | 0.207* | |
C16 | 0.7331 (4) | 0.2572 (3) | 0.3462 (3) | 0.1021 (15) | |
H16A | 0.7436 | 0.2444 | 0.3971 | 0.153* | |
H16B | 0.7717 | 0.2199 | 0.3257 | 0.153* | |
H16C | 0.661 | 0.2529 | 0.3199 | 0.153* | |
C20 | 0.4978 (3) | 0.5674 (2) | 0.2944 (2) | 0.0685 (10) | |
H20 | 0.5082 | 0.563 | 0.2456 | 0.082* | |
C22 | 0.5154 (4) | 0.6556 (3) | 0.3182 (3) | 0.1038 (16) | |
H22A | 0.5027 | 0.6624 | 0.3649 | 0.156* | |
H22B | 0.4692 | 0.6896 | 0.2822 | 0.156* | |
H22C | 0.5855 | 0.6705 | 0.3225 | 0.156* | |
C29 | 0.3863 (3) | 0.5423 (3) | 0.2864 (3) | 0.0958 (14) | |
H29A | 0.3759 | 0.4869 | 0.2701 | 0.144* | |
H29B | 0.3399 | 0.5769 | 0.251 | 0.144* | |
H29C | 0.373 | 0.5475 | 0.333 | 0.144* | |
C30 | 0.7780 (2) | 0.66672 (18) | 0.25228 (16) | 0.0466 (7) | |
C31 | 0.8656 (2) | 0.6669 (2) | 0.31442 (18) | 0.0561 (8) | |
C32 | 0.9316 (3) | 0.7323 (3) | 0.3230 (2) | 0.0731 (11) | |
H32 | 0.9908 | 0.7334 | 0.3631 | 0.088* | |
C34 | 0.9126 (3) | 0.7959 (3) | 0.2741 (3) | 0.0819 (12) | |
H34 | 0.9588 | 0.8391 | 0.281 | 0.098* | |
C36 | 0.8251 (3) | 0.7952 (2) | 0.2148 (2) | 0.0760 (11) | |
H36 | 0.8121 | 0.8389 | 0.1824 | 0.091* | |
C38 | 0.7550 (3) | 0.7308 (2) | 0.20209 (18) | 0.0573 (8) | |
C39 | 0.8838 (3) | 0.6004 (2) | 0.37121 (19) | 0.0733 (11) | |
H39 | 0.8478 | 0.5517 | 0.3468 | 0.088* | |
C41 | 0.8386 (4) | 0.6222 (4) | 0.4317 (3) | 0.1165 (18) | |
H41A | 0.8725 | 0.6697 | 0.4569 | 0.175* | |
H41B | 0.8481 | 0.5778 | 0.4658 | 0.175* | |
H41C | 0.7661 | 0.6331 | 0.4112 | 0.175* | |
C45 | 0.9976 (4) | 0.5784 (3) | 0.4038 (3) | 0.1144 (18) | |
H45A | 1.0269 | 0.5662 | 0.3648 | 0.172* | |
H45B | 1.0036 | 0.5316 | 0.435 | 0.172* | |
H45C | 1.0338 | 0.6233 | 0.4321 | 0.172* | |
C49 | 0.6570 (3) | 0.7340 (2) | 0.13710 (19) | 0.0713 (11) | |
H49 | 0.6258 | 0.6797 | 0.1325 | 0.086* | |
C51 | 0.6780 (5) | 0.7520 (5) | 0.0653 (3) | 0.160 (3) | |
H51A | 0.7081 | 0.8052 | 0.0674 | 0.24* | |
H51B | 0.6144 | 0.7501 | 0.026 | 0.24* | |
H51C | 0.7251 | 0.7123 | 0.0567 | 0.24* | |
C55 | 0.5784 (4) | 0.7925 (5) | 0.1494 (3) | 0.163 (3) | |
H55A | 0.5601 | 0.7767 | 0.1926 | 0.245* | |
H55B | 0.5178 | 0.7917 | 0.1076 | 0.245* | |
H55C | 0.607 | 0.8463 | 0.156 | 0.245* | |
C59 | 0.8399 (2) | 0.44663 (17) | 0.14842 (14) | 0.0388 (6) | |
C60 | 0.9260 (2) | 0.48751 (18) | 0.13918 (14) | 0.0436 (7) | |
C61 | 0.9679 (2) | 0.4595 (2) | 0.08533 (16) | 0.0526 (8) | |
H61 | 1.0249 | 0.486 | 0.0783 | 0.063* | |
C63 | 0.9276 (3) | 0.3937 (2) | 0.04231 (16) | 0.0574 (8) | |
H63 | 0.9557 | 0.3769 | 0.0056 | 0.069* | |
C65 | 0.8450 (2) | 0.3526 (2) | 0.05375 (16) | 0.0519 (8) | |
H65 | 0.8188 | 0.3074 | 0.0249 | 0.062* | |
C67 | 0.7996 (2) | 0.37687 (18) | 0.10719 (14) | 0.0418 (7) | |
C68 | 0.9736 (2) | 0.5593 (2) | 0.18655 (19) | 0.0567 (8) | |
H68 | 0.9359 | 0.5667 | 0.2229 | 0.068* | |
C70 | 0.9634 (5) | 0.6363 (3) | 0.1433 (3) | 0.124 (2) | |
H70A | 1.0068 | 0.6337 | 0.1116 | 0.186* | |
H70B | 0.9839 | 0.6815 | 0.1763 | 0.186* | |
H70C | 0.8927 | 0.6433 | 0.1141 | 0.186* | |
C74 | 1.0859 (3) | 0.5430 (3) | 0.2286 (3) | 0.141 (3) | |
H74A | 1.0899 | 0.4975 | 0.261 | 0.212* | |
H74B | 1.1149 | 0.5902 | 0.257 | 0.212* | |
H74C | 1.124 | 0.5311 | 0.1945 | 0.212* | |
C78 | 0.7160 (2) | 0.32381 (19) | 0.12179 (16) | 0.0480 (7) | |
H78 | 0.6878 | 0.3523 | 0.1568 | 0.058* | |
C80 | 0.7640 (3) | 0.2438 (2) | 0.1573 (2) | 0.0684 (10) | |
H80A | 0.791 | 0.2143 | 0.1235 | 0.103* | |
H80B | 0.712 | 0.2116 | 0.1694 | 0.103* | |
H80C | 0.8188 | 0.2552 | 0.2013 | 0.103* | |
C84 | 0.6269 (3) | 0.3064 (2) | 0.05232 (18) | 0.0685 (10) | |
H84A | 0.5969 | 0.3568 | 0.0308 | 0.103* | |
H84B | 0.5754 | 0.2743 | 0.0649 | 0.103* | |
H84C | 0.6526 | 0.2772 | 0.0177 | 0.103* | |
C93 | 0.4034 (3) | 0.3757 (3) | 0.1479 (2) | 0.0818 (12) | |
H93 | 0.4645 | 0.3558 | 0.18 | 0.098* | |
C95 | 0.3121 (3) | 0.3398 (3) | 0.1455 (2) | 0.0877 (13) | |
H95 | 0.3098 | 0.2957 | 0.1756 | 0.105* | |
C97 | 0.2242 (3) | 0.3698 (3) | 0.0979 (2) | 0.0858 (13) | |
H97 | 0.1608 | 0.346 | 0.0948 | 0.103* | |
C99 | 0.2293 (3) | 0.4341 (3) | 0.0554 (2) | 0.0940 (15) | |
H99 | 0.1694 | 0.4551 | 0.0229 | 0.113* | |
C101 | 0.3233 (3) | 0.4683 (3) | 0.0603 (2) | 0.0803 (12) | |
H101 | 0.3275 | 0.513 | 0.0313 | 0.096* | |
N103 | 0.4067 (2) | 0.4381 (2) | 0.10564 (16) | 0.0640 (8) | |
O88 | 0.71080 (14) | 0.60160 (12) | 0.24456 (9) | 0.0435 (5) | |
O89 | 0.79937 (13) | 0.47423 (12) | 0.20331 (9) | 0.0406 (4) | |
O90 | 0.63215 (13) | 0.45945 (12) | 0.24599 (9) | 0.0414 (5) | |
S92 | 0.59497 (6) | 0.52665 (5) | 0.09127 (4) | 0.0491 (2) | |
Si91 | 0.68648 (5) | 0.51703 (5) | 0.19649 (4) | 0.03759 (19) | |
H103 | 0.480 (4) | 0.465 (3) | 0.099 (2) | 0.132 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0452 (16) | 0.056 (2) | 0.0425 (14) | −0.0034 (14) | 0.0200 (12) | −0.0004 (14) |
C2 | 0.061 (2) | 0.067 (2) | 0.0460 (16) | 0.0037 (17) | 0.0196 (15) | 0.0095 (16) |
C3 | 0.094 (3) | 0.101 (3) | 0.052 (2) | 0.012 (3) | 0.026 (2) | 0.016 (2) |
C5 | 0.119 (4) | 0.124 (4) | 0.055 (2) | 0.012 (3) | 0.039 (2) | 0.005 (2) |
C7 | 0.099 (3) | 0.099 (3) | 0.076 (2) | 0.003 (3) | 0.058 (2) | −0.015 (2) |
C9 | 0.061 (2) | 0.065 (2) | 0.0622 (18) | 0.0026 (18) | 0.0351 (16) | −0.0035 (17) |
C10 | 0.071 (2) | 0.066 (3) | 0.0561 (19) | 0.0201 (19) | 0.0207 (17) | 0.0155 (17) |
C12 | 0.066 (3) | 0.130 (5) | 0.200 (6) | 0.023 (3) | 0.011 (3) | −0.044 (4) |
C16 | 0.130 (4) | 0.077 (3) | 0.110 (3) | −0.005 (3) | 0.052 (3) | 0.001 (3) |
C20 | 0.062 (2) | 0.066 (3) | 0.088 (2) | 0.0093 (19) | 0.0378 (19) | −0.001 (2) |
C22 | 0.080 (3) | 0.071 (3) | 0.162 (4) | 0.012 (2) | 0.037 (3) | −0.012 (3) |
C29 | 0.067 (3) | 0.087 (3) | 0.140 (4) | 0.001 (2) | 0.040 (3) | −0.012 (3) |
C30 | 0.0444 (17) | 0.0385 (18) | 0.0578 (17) | −0.0004 (14) | 0.0165 (14) | −0.0112 (14) |
C31 | 0.0454 (18) | 0.051 (2) | 0.0661 (19) | −0.0008 (15) | 0.0072 (15) | −0.0174 (16) |
C32 | 0.055 (2) | 0.064 (3) | 0.092 (3) | −0.0058 (19) | 0.0092 (19) | −0.025 (2) |
C34 | 0.074 (3) | 0.059 (3) | 0.117 (3) | −0.027 (2) | 0.034 (2) | −0.030 (2) |
C36 | 0.086 (3) | 0.048 (2) | 0.096 (3) | −0.012 (2) | 0.029 (2) | −0.005 (2) |
C38 | 0.065 (2) | 0.041 (2) | 0.067 (2) | −0.0043 (16) | 0.0204 (17) | −0.0069 (16) |
C39 | 0.067 (2) | 0.068 (3) | 0.065 (2) | −0.004 (2) | −0.0092 (18) | −0.0052 (19) |
C41 | 0.100 (4) | 0.155 (5) | 0.099 (3) | 0.008 (3) | 0.037 (3) | 0.025 (3) |
C45 | 0.092 (4) | 0.133 (5) | 0.095 (3) | 0.033 (3) | −0.008 (3) | 0.013 (3) |
C49 | 0.089 (3) | 0.046 (2) | 0.067 (2) | −0.006 (2) | 0.0042 (19) | 0.0051 (17) |
C51 | 0.131 (5) | 0.265 (9) | 0.076 (3) | 0.012 (5) | 0.018 (3) | 0.039 (4) |
C55 | 0.094 (4) | 0.233 (8) | 0.131 (5) | 0.064 (5) | −0.017 (3) | −0.041 (5) |
C59 | 0.0362 (15) | 0.0425 (17) | 0.0391 (13) | 0.0024 (12) | 0.0132 (11) | 0.0028 (12) |
C60 | 0.0385 (15) | 0.0442 (18) | 0.0495 (15) | −0.0010 (13) | 0.0152 (12) | 0.0051 (13) |
C61 | 0.0518 (18) | 0.060 (2) | 0.0565 (17) | −0.0003 (15) | 0.0322 (14) | 0.0056 (16) |
C63 | 0.065 (2) | 0.069 (2) | 0.0498 (17) | 0.0050 (18) | 0.0348 (15) | −0.0005 (17) |
C65 | 0.060 (2) | 0.053 (2) | 0.0461 (16) | −0.0016 (16) | 0.0214 (14) | −0.0063 (14) |
C67 | 0.0408 (15) | 0.0433 (18) | 0.0417 (14) | 0.0008 (13) | 0.0127 (12) | 0.0025 (13) |
C68 | 0.0531 (19) | 0.048 (2) | 0.078 (2) | −0.0087 (15) | 0.0323 (17) | −0.0072 (17) |
C70 | 0.230 (7) | 0.051 (3) | 0.125 (4) | −0.022 (3) | 0.106 (4) | −0.009 (3) |
C74 | 0.058 (3) | 0.142 (5) | 0.192 (5) | −0.004 (3) | −0.013 (3) | −0.091 (4) |
C78 | 0.0490 (18) | 0.0433 (19) | 0.0540 (17) | −0.0071 (14) | 0.0186 (14) | −0.0029 (14) |
C80 | 0.074 (2) | 0.052 (2) | 0.084 (2) | −0.0030 (19) | 0.0320 (19) | 0.0084 (19) |
C84 | 0.061 (2) | 0.072 (3) | 0.069 (2) | −0.0187 (19) | 0.0131 (18) | −0.0136 (18) |
C93 | 0.060 (2) | 0.083 (3) | 0.093 (3) | 0.002 (2) | 0.009 (2) | 0.024 (2) |
C95 | 0.078 (3) | 0.077 (3) | 0.112 (3) | −0.005 (2) | 0.033 (3) | 0.035 (3) |
C97 | 0.051 (2) | 0.105 (4) | 0.104 (3) | −0.011 (2) | 0.026 (2) | 0.013 (3) |
C99 | 0.056 (2) | 0.140 (4) | 0.085 (3) | 0.019 (3) | 0.019 (2) | 0.041 (3) |
C101 | 0.089 (3) | 0.095 (3) | 0.071 (2) | 0.016 (3) | 0.044 (2) | 0.035 (2) |
N103 | 0.0568 (18) | 0.067 (2) | 0.0738 (19) | −0.0095 (16) | 0.0283 (15) | 0.0018 (16) |
O88 | 0.0407 (11) | 0.0421 (12) | 0.0472 (10) | −0.0051 (9) | 0.0122 (8) | −0.0082 (9) |
O89 | 0.0344 (9) | 0.0506 (13) | 0.0388 (9) | 0.0006 (9) | 0.0138 (7) | −0.0026 (9) |
O90 | 0.0393 (10) | 0.0476 (13) | 0.0403 (9) | −0.0015 (9) | 0.0163 (8) | 0.0021 (8) |
S92 | 0.0458 (4) | 0.0547 (5) | 0.0426 (4) | −0.0065 (4) | 0.0064 (3) | 0.0030 (4) |
Si91 | 0.0331 (4) | 0.0415 (5) | 0.0385 (4) | −0.0024 (4) | 0.0112 (3) | −0.0013 (3) |
Geometric parameters (Å, º) top
C1—C9 | 1.391 (4) | C49—H49 | 0.98 |
C1—O90 | 1.400 (3) | C51—H51A | 0.96 |
C1—C2 | 1.404 (4) | C51—H51B | 0.96 |
C2—C3 | 1.401 (4) | C51—H51C | 0.96 |
C2—C10 | 1.502 (5) | C55—H55A | 0.96 |
C3—C5 | 1.355 (6) | C55—H55B | 0.96 |
C3—H3 | 0.93 | C55—H55C | 0.96 |
C5—C7 | 1.370 (6) | C59—O89 | 1.391 (3) |
C5—H5 | 0.93 | C59—C60 | 1.401 (4) |
C7—C9 | 1.408 (5) | C59—C67 | 1.406 (4) |
C7—H7 | 0.93 | C60—C61 | 1.389 (4) |
C9—C20 | 1.512 (5) | C60—C68 | 1.509 (4) |
C10—C12 | 1.505 (6) | C61—C63 | 1.369 (4) |
C10—C16 | 1.534 (6) | C61—H61 | 0.93 |
C10—H10 | 0.98 | C63—C65 | 1.378 (4) |
C12—H12A | 0.96 | C63—H63 | 0.93 |
C12—H12B | 0.96 | C65—C67 | 1.392 (4) |
C12—H12C | 0.96 | C65—H65 | 0.93 |
C16—H16A | 0.96 | C67—C78 | 1.519 (4) |
C16—H16B | 0.96 | C68—C70 | 1.496 (5) |
C16—H16C | 0.96 | C68—C74 | 1.519 (5) |
C20—C22 | 1.518 (5) | C68—H68 | 0.98 |
C20—C29 | 1.529 (5) | C70—H70A | 0.96 |
C20—H20 | 0.98 | C70—H70B | 0.96 |
C22—H22A | 0.96 | C70—H70C | 0.96 |
C22—H22B | 0.96 | C74—H74A | 0.96 |
C22—H22C | 0.96 | C74—H74B | 0.96 |
C29—H29A | 0.96 | C74—H74C | 0.96 |
C29—H29B | 0.96 | C78—C84 | 1.531 (4) |
C29—H29C | 0.96 | C78—C80 | 1.534 (4) |
C30—O88 | 1.385 (3) | C78—H78 | 0.98 |
C30—C38 | 1.394 (4) | C80—H80A | 0.96 |
C30—C31 | 1.406 (4) | C80—H80B | 0.96 |
C31—C32 | 1.377 (5) | C80—H80C | 0.96 |
C31—C39 | 1.506 (5) | C84—H84A | 0.96 |
C32—C34 | 1.373 (6) | C84—H84B | 0.96 |
C32—H32 | 0.93 | C84—H84C | 0.96 |
C34—C36 | 1.374 (5) | C93—N103 | 1.313 (5) |
C34—H34 | 0.93 | C93—C95 | 1.360 (5) |
C36—C38 | 1.395 (5) | C93—H93 | 0.93 |
C36—H36 | 0.93 | C95—C97 | 1.356 (5) |
C38—C49 | 1.524 (5) | C95—H95 | 0.93 |
C39—C41 | 1.499 (6) | C97—C99 | 1.345 (6) |
C39—C45 | 1.524 (5) | C97—H97 | 0.93 |
C39—H39 | 0.98 | C99—C101 | 1.370 (6) |
C41—H41A | 0.96 | C99—H99 | 0.93 |
C41—H41B | 0.96 | C101—N103 | 1.301 (5) |
C41—H41C | 0.96 | C101—H101 | 0.93 |
C45—H45A | 0.96 | N103—H103 | 1.12 (5) |
C45—H45B | 0.96 | O88—Si91 | 1.644 (2) |
C45—H45C | 0.96 | O89—Si91 | 1.6528 (19) |
C49—C55 | 1.504 (7) | O90—Si91 | 1.6533 (19) |
C49—C51 | 1.505 (6) | S92—Si91 | 2.0254 (10) |
| | | |
C9—C1—O90 | 118.9 (3) | C38—C49—H49 | 106.9 |
C9—C1—C2 | 122.9 (3) | C49—C51—H51A | 109.5 |
O90—C1—C2 | 118.2 (3) | C49—C51—H51B | 109.5 |
C3—C2—C1 | 116.5 (3) | H51A—C51—H51B | 109.5 |
C3—C2—C10 | 120.6 (3) | C49—C51—H51C | 109.5 |
C1—C2—C10 | 122.8 (3) | H51A—C51—H51C | 109.5 |
C5—C3—C2 | 122.4 (4) | H51B—C51—H51C | 109.5 |
C5—C3—H3 | 118.8 | C49—C55—H55A | 109.5 |
C2—C3—H3 | 118.8 | C49—C55—H55B | 109.5 |
C3—C5—C7 | 119.7 (4) | H55A—C55—H55B | 109.5 |
C3—C5—H5 | 120.1 | C49—C55—H55C | 109.5 |
C7—C5—H5 | 120.1 | H55A—C55—H55C | 109.5 |
C5—C7—C9 | 121.9 (4) | H55B—C55—H55C | 109.5 |
C5—C7—H7 | 119 | O89—C59—C60 | 117.7 (2) |
C9—C7—H7 | 119 | O89—C59—C67 | 120.8 (2) |
C1—C9—C7 | 116.5 (3) | C60—C59—C67 | 121.4 (3) |
C1—C9—C20 | 122.5 (3) | C61—C60—C59 | 118.0 (3) |
C7—C9—C20 | 121.0 (3) | C61—C60—C68 | 120.3 (3) |
C2—C10—C12 | 114.0 (3) | C59—C60—C68 | 121.7 (3) |
C2—C10—C16 | 111.1 (3) | C63—C61—C60 | 121.7 (3) |
C12—C10—C16 | 110.3 (4) | C63—C61—H61 | 119.2 |
C2—C10—H10 | 107 | C60—C61—H61 | 119.2 |
C12—C10—H10 | 107 | C61—C63—C65 | 119.5 (3) |
C16—C10—H10 | 107 | C61—C63—H63 | 120.2 |
C10—C12—H12A | 109.5 | C65—C63—H63 | 120.2 |
C10—C12—H12B | 109.5 | C63—C65—C67 | 121.9 (3) |
H12A—C12—H12B | 109.5 | C63—C65—H65 | 119.1 |
C10—C12—H12C | 109.5 | C67—C65—H65 | 119.1 |
H12A—C12—H12C | 109.5 | C65—C67—C59 | 117.4 (3) |
H12B—C12—H12C | 109.5 | C65—C67—C78 | 118.8 (3) |
C10—C16—H16A | 109.5 | C59—C67—C78 | 123.6 (3) |
C10—C16—H16B | 109.5 | C70—C68—C60 | 112.3 (3) |
H16A—C16—H16B | 109.5 | C70—C68—C74 | 110.8 (4) |
C10—C16—H16C | 109.5 | C60—C68—C74 | 111.2 (3) |
H16A—C16—H16C | 109.5 | C70—C68—H68 | 107.4 |
H16B—C16—H16C | 109.5 | C60—C68—H68 | 107.4 |
C9—C20—C22 | 111.8 (3) | C74—C68—H68 | 107.4 |
C9—C20—C29 | 112.1 (3) | C68—C70—H70A | 109.5 |
C22—C20—C29 | 110.5 (3) | C68—C70—H70B | 109.5 |
C9—C20—H20 | 107.4 | H70A—C70—H70B | 109.5 |
C22—C20—H20 | 107.4 | C68—C70—H70C | 109.5 |
C29—C20—H20 | 107.4 | H70A—C70—H70C | 109.5 |
C20—C22—H22A | 109.5 | H70B—C70—H70C | 109.5 |
C20—C22—H22B | 109.5 | C68—C74—H74A | 109.5 |
H22A—C22—H22B | 109.5 | C68—C74—H74B | 109.5 |
C20—C22—H22C | 109.5 | H74A—C74—H74B | 109.5 |
H22A—C22—H22C | 109.5 | C68—C74—H74C | 109.5 |
H22B—C22—H22C | 109.5 | H74A—C74—H74C | 109.5 |
C20—C29—H29A | 109.5 | H74B—C74—H74C | 109.5 |
C20—C29—H29B | 109.5 | C67—C78—C84 | 112.9 (3) |
H29A—C29—H29B | 109.5 | C67—C78—C80 | 109.4 (3) |
C20—C29—H29C | 109.5 | C84—C78—C80 | 110.1 (3) |
H29A—C29—H29C | 109.5 | C67—C78—H78 | 108.1 |
H29B—C29—H29C | 109.5 | C84—C78—H78 | 108.1 |
O88—C30—C38 | 120.3 (3) | C80—C78—H78 | 108.1 |
O88—C30—C31 | 117.1 (3) | C78—C80—H80A | 109.5 |
C38—C30—C31 | 122.5 (3) | C78—C80—H80B | 109.5 |
C32—C31—C30 | 117.3 (3) | H80A—C80—H80B | 109.5 |
C32—C31—C39 | 121.3 (3) | C78—C80—H80C | 109.5 |
C30—C31—C39 | 121.4 (3) | H80A—C80—H80C | 109.5 |
C34—C32—C31 | 122.0 (3) | H80B—C80—H80C | 109.5 |
C34—C32—H32 | 119 | C78—C84—H84A | 109.5 |
C31—C32—H32 | 119 | C78—C84—H84B | 109.5 |
C32—C34—C36 | 119.6 (4) | H84A—C84—H84B | 109.5 |
C32—C34—H34 | 120.2 | C78—C84—H84C | 109.5 |
C36—C34—H34 | 120.2 | H84A—C84—H84C | 109.5 |
C34—C36—C38 | 121.8 (4) | H84B—C84—H84C | 109.5 |
C34—C36—H36 | 119.1 | N103—C93—C95 | 120.9 (4) |
C38—C36—H36 | 119.1 | N103—C93—H93 | 119.5 |
C30—C38—C36 | 116.8 (3) | C95—C93—H93 | 119.5 |
C30—C38—C49 | 123.2 (3) | C97—C95—C93 | 118.3 (4) |
C36—C38—C49 | 120.0 (3) | C97—C95—H95 | 120.8 |
C41—C39—C31 | 111.1 (4) | C93—C95—H95 | 120.8 |
C41—C39—C45 | 109.7 (3) | C99—C97—C95 | 119.8 (4) |
C31—C39—C45 | 113.4 (4) | C99—C97—H97 | 120.1 |
C41—C39—H39 | 107.5 | C95—C97—H97 | 120.1 |
C31—C39—H39 | 107.5 | C97—C99—C101 | 119.6 (4) |
C45—C39—H39 | 107.5 | C97—C99—H99 | 120.2 |
C39—C41—H41A | 109.5 | C101—C99—H99 | 120.2 |
C39—C41—H41B | 109.5 | N103—C101—C99 | 119.7 (4) |
H41A—C41—H41B | 109.5 | N103—C101—H101 | 120.2 |
C39—C41—H41C | 109.5 | C99—C101—H101 | 120.2 |
H41A—C41—H41C | 109.5 | C101—N103—C93 | 121.7 (4) |
H41B—C41—H41C | 109.5 | C101—N103—H103 | 113 (2) |
C39—C45—H45A | 109.5 | C93—N103—H103 | 125 (2) |
C39—C45—H45B | 109.5 | C30—O88—Si91 | 136.96 (18) |
H45A—C45—H45B | 109.5 | C59—O89—Si91 | 129.81 (15) |
C39—C45—H45C | 109.5 | C1—O90—Si91 | 132.00 (18) |
H45A—C45—H45C | 109.5 | O88—Si91—O89 | 106.73 (10) |
H45B—C45—H45C | 109.5 | O88—Si91—O90 | 102.57 (10) |
C55—C49—C51 | 110.3 (5) | O89—Si91—O90 | 105.53 (10) |
C55—C49—C38 | 112.5 (3) | O88—Si91—S92 | 116.57 (8) |
C51—C49—C38 | 113.0 (4) | O89—Si91—S92 | 113.13 (7) |
C55—C49—H49 | 106.9 | O90—Si91—S92 | 111.24 (7) |
C51—C49—H49 | 106.9 | | |
| | | |
C9—C1—C2—C3 | −1.5 (5) | O89—C59—C60—C61 | 178.9 (2) |
O90—C1—C2—C3 | −178.5 (3) | C67—C59—C60—C61 | 3.1 (4) |
C9—C1—C2—C10 | 174.5 (3) | O89—C59—C60—C68 | −0.2 (4) |
O90—C1—C2—C10 | −2.5 (5) | C67—C59—C60—C68 | −176.1 (3) |
C1—C2—C3—C5 | 0.0 (6) | C59—C60—C61—C63 | −0.3 (4) |
C10—C2—C3—C5 | −176.1 (4) | C68—C60—C61—C63 | 178.9 (3) |
C2—C3—C5—C7 | 1.4 (7) | C60—C61—C63—C65 | −1.8 (5) |
C3—C5—C7—C9 | −1.4 (7) | C61—C63—C65—C67 | 1.2 (5) |
O90—C1—C9—C7 | 178.4 (3) | C63—C65—C67—C59 | 1.5 (4) |
C2—C1—C9—C7 | 1.5 (5) | C63—C65—C67—C78 | −174.0 (3) |
O90—C1—C9—C20 | 0.0 (5) | O89—C59—C67—C65 | −179.4 (2) |
C2—C1—C9—C20 | −177.0 (3) | C60—C59—C67—C65 | −3.6 (4) |
C5—C7—C9—C1 | 0.0 (6) | O89—C59—C67—C78 | −4.2 (4) |
C5—C7—C9—C20 | 178.4 (4) | C60—C59—C67—C78 | 171.6 (3) |
C3—C2—C10—C12 | −60.9 (5) | C61—C60—C68—C70 | 66.0 (4) |
C1—C2—C10—C12 | 123.3 (4) | C59—C60—C68—C70 | −114.8 (4) |
C3—C2—C10—C16 | 64.5 (5) | C61—C60—C68—C74 | −58.8 (5) |
C1—C2—C10—C16 | −111.3 (4) | C59—C60—C68—C74 | 120.3 (4) |
C1—C9—C20—C22 | −123.0 (4) | C65—C67—C78—C84 | −54.7 (4) |
C7—C9—C20—C22 | 58.6 (5) | C59—C67—C78—C84 | 130.2 (3) |
C1—C9—C20—C29 | 112.3 (4) | C65—C67—C78—C80 | 68.3 (3) |
C7—C9—C20—C29 | −66.1 (5) | C59—C67—C78—C80 | −106.8 (3) |
O88—C30—C31—C32 | −178.8 (3) | N103—C93—C95—C97 | 0.3 (7) |
C38—C30—C31—C32 | −2.5 (5) | C93—C95—C97—C99 | −0.7 (7) |
O88—C30—C31—C39 | −1.7 (5) | C95—C97—C99—C101 | 0.4 (8) |
C38—C30—C31—C39 | 174.7 (3) | C97—C99—C101—N103 | 0.4 (7) |
C30—C31—C32—C34 | 1.2 (6) | C99—C101—N103—C93 | −0.8 (6) |
C39—C31—C32—C34 | −175.9 (4) | C95—C93—N103—C101 | 0.5 (7) |
C31—C32—C34—C36 | 0.4 (6) | C38—C30—O88—Si91 | 82.4 (4) |
C32—C34—C36—C38 | −1.0 (6) | C31—C30—O88—Si91 | −101.1 (3) |
O88—C30—C38—C36 | 178.2 (3) | C60—C59—O89—Si91 | 113.6 (2) |
C31—C30—C38—C36 | 1.9 (5) | C67—C59—O89—Si91 | −70.5 (3) |
O88—C30—C38—C49 | 0.2 (5) | C9—C1—O90—Si91 | 85.2 (3) |
C31—C30—C38—C49 | −176.1 (3) | C2—C1—O90—Si91 | −97.7 (3) |
C34—C36—C38—C30 | −0.1 (6) | C30—O88—Si91—O89 | 46.1 (3) |
C34—C36—C38—C49 | 177.9 (4) | C30—O88—Si91—O90 | 156.8 (3) |
C32—C31—C39—C41 | 85.3 (5) | C30—O88—Si91—S92 | −81.4 (3) |
C30—C31—C39—C41 | −91.8 (4) | C59—O89—Si91—O88 | −127.8 (2) |
C32—C31—C39—C45 | −38.9 (5) | C59—O89—Si91—O90 | 123.6 (2) |
C30—C31—C39—C45 | 144.1 (4) | C59—O89—Si91—S92 | 1.7 (3) |
C30—C38—C49—C55 | 104.5 (5) | C1—O90—Si91—O88 | −24.9 (3) |
C36—C38—C49—C55 | −73.4 (6) | C1—O90—Si91—O89 | 86.7 (2) |
C30—C38—C49—C51 | −129.8 (5) | C1—O90—Si91—S92 | −150.3 (2) |
C36—C38—C49—C51 | 52.3 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N103—H103···S92 | 1.12 (5) | 1.90 (5) | 3.017 (3) | 172 (4) |