Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620014481/dk5101sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014481/dk5101Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620014481/dk5101sup3.pdf |
CCDC reference: 1960049
Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28c; cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28c; data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28c; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2018); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018).
C25H34O2S | Dx = 1.177 Mg m−3 |
Mr = 398.58 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pca21 | Cell parameters from 5154 reflections |
a = 54.285 (5) Å | θ = 3.2–72.5° |
b = 5.5843 (3) Å | µ = 1.40 mm−1 |
c = 14.8411 (10) Å | T = 90 K |
V = 4499.0 (5) Å3 | Needle, colourless |
Z = 8 | 0.38 × 0.02 × 0.01 mm |
F(000) = 1728 |
SuperNova diffractometer (Agilent Technologies) with Atlas detector | 8461 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 5907 reflections with I > 2σ(I) |
Detector resolution: 10.4498 pixels mm-1 | Rint = 0.113 |
ω scans | θmax = 70.1°, θmin = 3.3° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.28c Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −65→66 |
Tmin = 0.562, Tmax = 1.000 | k = −6→4 |
34886 measured reflections | l = −18→17 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.115 | w = 1/[σ2(Fo2) + (0.0856P)2 + 26.8267P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.299 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.71 e Å−3 |
8461 reflections | Δρmin = −0.87 e Å−3 |
456 parameters | Absolute structure: Refined as an inversion twin. |
1 restraint | Absolute structure parameter: 0.53 (7) |
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. |
Refinement. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.70254 (5) | 1.0527 (5) | 0.5261 (2) | 0.0284 (6) | |
O1 | 0.81714 (12) | 0.6704 (13) | 0.5206 (6) | 0.0233 (16) | |
O2 | 0.70193 (14) | 0.6414 (14) | 0.4367 (5) | 0.0270 (18) | |
C1 | 0.9562 (2) | −0.125 (2) | 0.4845 (13) | 0.051 (4) | |
H1A | 0.948242 | −0.276140 | 0.501254 | 0.076* | |
H1B | 0.972695 | −0.118103 | 0.510798 | 0.076* | |
H1C | 0.957359 | −0.114412 | 0.418718 | 0.076* | |
C2 | 0.9408 (2) | 0.084 (2) | 0.5198 (10) | 0.037 (3) | |
H2A | 0.940673 | 0.080157 | 0.586526 | 0.044* | |
H2B | 0.948525 | 0.236858 | 0.500858 | 0.044* | |
C3 | 0.9144 (2) | 0.075 (2) | 0.4850 (10) | 0.033 (3) | |
H3A | 0.914712 | 0.079526 | 0.418370 | 0.040* | |
H3B | 0.906939 | −0.079266 | 0.503312 | 0.040* | |
C4 | 0.89805 (19) | 0.278 (2) | 0.5189 (9) | 0.030 (3) | |
H4A | 0.898054 | 0.276596 | 0.585568 | 0.036* | |
H4B | 0.905265 | 0.432720 | 0.499264 | 0.036* | |
C5 | 0.8715 (2) | 0.266 (2) | 0.4859 (10) | 0.032 (3) | |
H5A | 0.871431 | 0.263492 | 0.419240 | 0.039* | |
H5B | 0.864027 | 0.114325 | 0.507244 | 0.039* | |
C6 | 0.85616 (19) | 0.475 (2) | 0.5189 (9) | 0.029 (3) | |
H6A | 0.857308 | 0.484389 | 0.585351 | 0.035* | |
H6B | 0.862963 | 0.625358 | 0.493788 | 0.035* | |
C7 | 0.8297 (2) | 0.454 (2) | 0.4924 (8) | 0.030 (3) | |
H7A | 0.828286 | 0.433943 | 0.426297 | 0.036* | |
H7B | 0.822170 | 0.312504 | 0.521816 | 0.036* | |
C8 | 0.7924 (2) | 0.684 (2) | 0.5076 (7) | 0.024 (2) | |
C9 | 0.78118 (19) | 0.8933 (18) | 0.5403 (7) | 0.0215 (16) | |
H9 | 0.790929 | 1.014788 | 0.567403 | 0.026* | |
C10 | 0.75625 (18) | 0.9225 (18) | 0.5330 (8) | 0.0215 (16) | |
H10 | 0.748770 | 1.060062 | 0.558910 | 0.026* | |
C11 | 0.74165 (19) | 0.7567 (19) | 0.4891 (7) | 0.0206 (16) | |
C12 | 0.7531 (2) | 0.5488 (18) | 0.4545 (7) | 0.0206 (16) | |
H12 | 0.743390 | 0.430408 | 0.425124 | 0.025* | |
C13 | 0.7783 (2) | 0.5163 (19) | 0.4630 (7) | 0.022 (2) | |
H13 | 0.785839 | 0.377970 | 0.438071 | 0.026* | |
C14 | 0.7145 (2) | 0.7824 (18) | 0.4766 (7) | 0.021 (2) | |
C15 | 0.6707 (2) | 1.0303 (18) | 0.5073 (8) | 0.0220 (17) | |
C16 | 0.6586 (2) | 1.2189 (18) | 0.4625 (7) | 0.0220 (17) | |
H16 | 0.667699 | 1.349052 | 0.438403 | 0.026* | |
C17 | 0.6331 (2) | 1.2129 (19) | 0.4538 (8) | 0.0235 (17) | |
H17 | 0.625037 | 1.344025 | 0.425715 | 0.028* | |
C18 | 0.6190 (2) | 1.0219 (18) | 0.4848 (8) | 0.0235 (17) | |
C19 | 0.6314 (2) | 0.831 (2) | 0.5259 (9) | 0.028 (2) | |
H19 | 0.622289 | 0.698177 | 0.547804 | 0.033* | |
C20 | 0.6571 (2) | 0.8326 (19) | 0.5352 (9) | 0.028 (3) | |
H20 | 0.665253 | 0.698176 | 0.560725 | 0.033* | |
C21 | 0.5915 (2) | 1.024 (2) | 0.4737 (9) | 0.029 (3) | |
H21A | 0.587813 | 1.036311 | 0.408563 | 0.035* | |
H21B | 0.585117 | 1.171635 | 0.502604 | 0.035* | |
C22 | 0.5772 (2) | 0.813 (2) | 0.5113 (8) | 0.030 (3) | |
H22A | 0.584302 | 0.663579 | 0.486569 | 0.036* | |
H22B | 0.579386 | 0.809190 | 0.577505 | 0.036* | |
C23 | 0.5501 (2) | 0.818 (2) | 0.4905 (10) | 0.036 (3) | |
H23A | 0.547893 | 0.822104 | 0.424247 | 0.043* | |
H23B | 0.542982 | 0.968040 | 0.515116 | 0.043* | |
C24 | 0.5358 (2) | 0.607 (2) | 0.5281 (11) | 0.045 (3) | |
H24A | 0.538015 | 0.603603 | 0.594342 | 0.054* | |
H24B | 0.542909 | 0.457785 | 0.503480 | 0.054* | |
C25 | 0.5084 (2) | 0.611 (3) | 0.5076 (12) | 0.052 (4) | |
H25A | 0.501542 | 0.767157 | 0.524106 | 0.078* | |
H25B | 0.500129 | 0.485025 | 0.542306 | 0.078* | |
H25C | 0.505829 | 0.582671 | 0.443094 | 0.078* | |
S2 | 0.81465 (5) | 0.5362 (5) | 0.2188 (2) | 0.0321 (7) | |
O3 | 0.69885 (13) | 0.1982 (13) | 0.2227 (6) | 0.0268 (18) | |
O4 | 0.81437 (14) | 0.1144 (13) | 0.3015 (6) | 0.0267 (18) | |
C31 | 0.5588 (2) | −0.579 (2) | 0.2692 (12) | 0.049 (4) | |
H31A | 0.564954 | −0.728314 | 0.243345 | 0.074* | |
H31B | 0.541513 | −0.555919 | 0.251583 | 0.074* | |
H31C | 0.559915 | −0.585833 | 0.335071 | 0.074* | |
C32 | 0.5741 (2) | −0.369 (2) | 0.2345 (11) | 0.038 (3) | |
H32A | 0.573327 | −0.367095 | 0.167853 | 0.045* | |
H32B | 0.566809 | −0.217827 | 0.256608 | 0.045* | |
C33 | 0.6008 (2) | −0.378 (2) | 0.2629 (9) | 0.034 (3) | |
H33A | 0.601449 | −0.383781 | 0.329544 | 0.040* | |
H33B | 0.608017 | −0.529809 | 0.240312 | 0.040* | |
C34 | 0.6168 (2) | −0.175 (2) | 0.2314 (9) | 0.032 (3) | |
H34A | 0.609978 | −0.023654 | 0.255975 | 0.039* | |
H34B | 0.615690 | −0.165337 | 0.164921 | 0.039* | |
C35 | 0.6435 (2) | −0.191 (2) | 0.2574 (8) | 0.026 (2) | |
H35A | 0.650396 | −0.340706 | 0.232263 | 0.031* | |
H35B | 0.644629 | −0.201394 | 0.323863 | 0.031* | |
C36 | 0.65937 (19) | 0.019 (2) | 0.2256 (8) | 0.025 (2) | |
H36A | 0.658320 | 0.031630 | 0.159201 | 0.030* | |
H36B | 0.652901 | 0.169428 | 0.251710 | 0.030* | |
C37 | 0.6859 (2) | −0.011 (2) | 0.2527 (9) | 0.030 (3) | |
H37A | 0.687219 | −0.027321 | 0.318959 | 0.037* | |
H37B | 0.692898 | −0.156391 | 0.224416 | 0.037* | |
C38 | 0.7237 (2) | 0.2029 (18) | 0.2367 (7) | 0.0217 (10) | |
C39 | 0.7371 (2) | 0.0252 (19) | 0.2793 (7) | 0.0217 (10) | |
H39 | 0.728971 | −0.110623 | 0.303848 | 0.026* | |
C40 | 0.7626 (2) | 0.0463 (19) | 0.2860 (7) | 0.0217 (10) | |
H40 | 0.771823 | −0.077852 | 0.313775 | 0.026* | |
C41 | 0.7747 (2) | 0.2490 (18) | 0.2523 (8) | 0.0217 (10) | |
C42 | 0.76084 (19) | 0.4248 (18) | 0.2098 (7) | 0.0217 (10) | |
H42 | 0.768912 | 0.560140 | 0.184672 | 0.026* | |
C43 | 0.73565 (19) | 0.4065 (18) | 0.2034 (7) | 0.0217 (10) | |
H43 | 0.726388 | 0.531748 | 0.176338 | 0.026* | |
C44 | 0.8018 (2) | 0.2642 (18) | 0.2628 (7) | 0.021 (2) | |
C45 | 0.8464 (2) | 0.4997 (18) | 0.2383 (7) | 0.022 (2) | |
C46 | 0.8597 (2) | 0.3110 (18) | 0.2039 (8) | 0.025 (3) | |
H46 | 0.851341 | 0.186616 | 0.172673 | 0.030* | |
C47 | 0.88527 (19) | 0.2989 (18) | 0.2142 (8) | 0.023 (2) | |
H47 | 0.894132 | 0.167360 | 0.189755 | 0.028* | |
C48 | 0.8979 (2) | 0.482 (2) | 0.2606 (9) | 0.027 (3) | |
C49 | 0.8842 (2) | 0.6700 (18) | 0.2939 (8) | 0.027 (2) | |
H49 | 0.892408 | 0.796441 | 0.324302 | 0.032* | |
C50 | 0.8589 (2) | 0.681 (2) | 0.2844 (8) | 0.027 (3) | |
H50 | 0.849993 | 0.811941 | 0.309280 | 0.032* | |
C51 | 0.9255 (2) | 0.474 (2) | 0.2752 (8) | 0.029 (3) | |
H51A | 0.928563 | 0.481097 | 0.340883 | 0.034* | |
H51B | 0.932645 | 0.620433 | 0.248403 | 0.034* | |
C52 | 0.9395 (2) | 0.261 (2) | 0.2382 (9) | 0.031 (3) | |
H52A | 0.937408 | 0.256868 | 0.171907 | 0.038* | |
H52B | 0.932267 | 0.112607 | 0.263033 | 0.038* | |
C53 | 0.9668 (2) | 0.266 (2) | 0.2598 (10) | 0.038 (3) | |
H53A | 0.973893 | 0.418207 | 0.237511 | 0.046* | |
H53B | 0.968925 | 0.262618 | 0.326057 | 0.046* | |
C54 | 0.9811 (2) | 0.062 (2) | 0.2197 (12) | 0.046 (4) | |
H54A | 0.978784 | 0.064789 | 0.153533 | 0.055* | |
H54B | 0.973946 | −0.090121 | 0.242207 | 0.055* | |
C55 | 1.0084 (3) | 0.062 (3) | 0.2397 (13) | 0.065 (5) | |
H55A | 1.015667 | 0.212678 | 0.218903 | 0.098* | |
H55B | 1.016249 | −0.072462 | 0.208327 | 0.098* | |
H55C | 1.010985 | 0.045278 | 0.304733 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0266 (14) | 0.0289 (14) | 0.0297 (15) | −0.0006 (11) | −0.0009 (12) | −0.0067 (14) |
O1 | 0.024 (4) | 0.023 (4) | 0.022 (4) | 0.002 (3) | 0.000 (3) | −0.004 (4) |
O2 | 0.031 (4) | 0.024 (4) | 0.025 (4) | 0.001 (3) | −0.006 (3) | −0.007 (4) |
C1 | 0.031 (7) | 0.036 (8) | 0.086 (12) | 0.002 (5) | 0.003 (7) | 0.003 (8) |
C2 | 0.028 (6) | 0.035 (7) | 0.047 (8) | 0.007 (5) | −0.002 (6) | 0.000 (6) |
C3 | 0.026 (6) | 0.030 (6) | 0.043 (8) | −0.007 (5) | 0.000 (5) | −0.011 (6) |
C4 | 0.030 (6) | 0.027 (6) | 0.034 (7) | −0.004 (4) | 0.000 (5) | −0.011 (6) |
C5 | 0.028 (6) | 0.031 (6) | 0.038 (7) | −0.001 (5) | 0.001 (5) | −0.004 (6) |
C6 | 0.025 (6) | 0.031 (6) | 0.031 (7) | 0.000 (4) | 0.002 (5) | 0.004 (6) |
C7 | 0.023 (6) | 0.035 (7) | 0.030 (7) | 0.000 (5) | 0.005 (5) | 0.002 (6) |
C8 | 0.027 (6) | 0.027 (6) | 0.017 (6) | −0.001 (4) | −0.006 (4) | 0.001 (5) |
C9 | 0.030 (4) | 0.016 (4) | 0.019 (4) | −0.002 (3) | −0.001 (3) | −0.005 (3) |
C10 | 0.030 (4) | 0.016 (4) | 0.019 (4) | −0.002 (3) | −0.001 (3) | −0.005 (3) |
C11 | 0.028 (4) | 0.018 (3) | 0.016 (4) | −0.006 (3) | 0.003 (3) | −0.007 (3) |
C12 | 0.028 (4) | 0.018 (3) | 0.016 (4) | −0.006 (3) | 0.003 (3) | −0.007 (3) |
C13 | 0.029 (6) | 0.018 (5) | 0.018 (5) | −0.002 (4) | 0.003 (4) | −0.004 (4) |
C14 | 0.036 (6) | 0.020 (5) | 0.007 (5) | 0.004 (4) | 0.000 (4) | −0.003 (4) |
C15 | 0.033 (4) | 0.009 (3) | 0.024 (4) | 0.003 (3) | 0.004 (3) | −0.004 (3) |
C16 | 0.033 (4) | 0.009 (3) | 0.024 (4) | 0.003 (3) | 0.004 (3) | −0.004 (3) |
C17 | 0.036 (5) | 0.012 (4) | 0.023 (4) | 0.002 (3) | 0.002 (3) | −0.010 (3) |
C18 | 0.036 (5) | 0.012 (4) | 0.023 (4) | 0.002 (3) | 0.002 (3) | −0.010 (3) |
C19 | 0.029 (6) | 0.032 (6) | 0.022 (6) | 0.000 (4) | 0.000 (5) | −0.001 (6) |
C20 | 0.034 (6) | 0.020 (6) | 0.030 (7) | −0.003 (4) | 0.004 (5) | 0.001 (5) |
C21 | 0.036 (7) | 0.020 (6) | 0.032 (7) | 0.002 (5) | 0.003 (5) | −0.009 (5) |
C22 | 0.036 (6) | 0.024 (6) | 0.029 (7) | 0.002 (5) | 0.002 (5) | −0.009 (5) |
C23 | 0.031 (7) | 0.028 (6) | 0.049 (8) | 0.001 (5) | −0.002 (6) | −0.002 (6) |
C24 | 0.029 (7) | 0.049 (8) | 0.056 (9) | −0.004 (5) | −0.005 (7) | −0.003 (8) |
C25 | 0.032 (7) | 0.052 (9) | 0.070 (12) | −0.001 (6) | −0.007 (7) | 0.003 (8) |
S2 | 0.0255 (14) | 0.0320 (15) | 0.0387 (18) | −0.0015 (11) | −0.0004 (13) | 0.0052 (16) |
O3 | 0.026 (4) | 0.027 (4) | 0.028 (5) | 0.000 (3) | 0.001 (4) | −0.002 (4) |
O4 | 0.033 (4) | 0.018 (4) | 0.029 (5) | 0.002 (3) | −0.002 (3) | −0.001 (3) |
C31 | 0.027 (7) | 0.045 (8) | 0.076 (11) | −0.002 (6) | −0.003 (7) | −0.009 (8) |
C32 | 0.020 (6) | 0.037 (7) | 0.056 (9) | 0.001 (5) | 0.003 (6) | −0.011 (7) |
C33 | 0.031 (7) | 0.037 (7) | 0.033 (7) | −0.003 (5) | 0.000 (5) | −0.002 (6) |
C34 | 0.027 (6) | 0.041 (7) | 0.029 (7) | 0.001 (5) | 0.004 (5) | −0.004 (6) |
C35 | 0.033 (6) | 0.028 (6) | 0.016 (5) | −0.001 (5) | 0.003 (5) | −0.003 (5) |
C36 | 0.026 (6) | 0.029 (6) | 0.021 (6) | 0.001 (4) | 0.001 (5) | −0.006 (5) |
C37 | 0.024 (6) | 0.031 (6) | 0.036 (7) | 0.001 (5) | 0.002 (5) | −0.006 (5) |
C38 | 0.029 (2) | 0.017 (2) | 0.018 (2) | 0.0014 (17) | −0.0002 (19) | −0.009 (2) |
C39 | 0.029 (2) | 0.017 (2) | 0.018 (2) | 0.0014 (17) | −0.0002 (19) | −0.009 (2) |
C40 | 0.029 (2) | 0.017 (2) | 0.018 (2) | 0.0014 (17) | −0.0002 (19) | −0.009 (2) |
C41 | 0.029 (2) | 0.017 (2) | 0.018 (2) | 0.0014 (17) | −0.0002 (19) | −0.009 (2) |
C42 | 0.029 (2) | 0.017 (2) | 0.018 (2) | 0.0014 (17) | −0.0002 (19) | −0.009 (2) |
C43 | 0.029 (2) | 0.017 (2) | 0.018 (2) | 0.0014 (17) | −0.0002 (19) | −0.009 (2) |
C44 | 0.030 (6) | 0.020 (5) | 0.012 (5) | 0.002 (4) | 0.002 (4) | −0.002 (4) |
C45 | 0.034 (6) | 0.011 (5) | 0.022 (6) | −0.004 (4) | 0.004 (5) | −0.009 (4) |
C46 | 0.042 (7) | 0.013 (5) | 0.019 (6) | −0.007 (4) | −0.001 (5) | 0.000 (5) |
C47 | 0.030 (6) | 0.016 (5) | 0.023 (6) | −0.003 (4) | 0.004 (5) | 0.000 (5) |
C48 | 0.022 (6) | 0.030 (6) | 0.030 (6) | −0.004 (5) | 0.000 (5) | −0.003 (5) |
C49 | 0.041 (7) | 0.009 (5) | 0.031 (6) | −0.002 (4) | −0.002 (5) | 0.000 (5) |
C50 | 0.038 (7) | 0.019 (6) | 0.023 (6) | 0.003 (5) | 0.004 (5) | 0.003 (5) |
C51 | 0.034 (7) | 0.024 (6) | 0.027 (6) | −0.001 (5) | −0.003 (5) | −0.004 (5) |
C52 | 0.028 (6) | 0.032 (6) | 0.034 (7) | −0.002 (5) | −0.002 (5) | 0.000 (5) |
C53 | 0.032 (7) | 0.032 (7) | 0.051 (8) | 0.001 (5) | −0.002 (6) | 0.000 (6) |
C54 | 0.033 (7) | 0.042 (8) | 0.063 (10) | 0.003 (5) | −0.002 (7) | −0.019 (8) |
C55 | 0.038 (8) | 0.066 (11) | 0.092 (14) | 0.011 (7) | −0.010 (8) | −0.023 (10) |
S1—C15 | 1.753 (12) | S2—C45 | 1.759 (11) |
S1—C14 | 1.800 (11) | S2—C44 | 1.795 (11) |
O1—C8 | 1.358 (13) | O3—C38 | 1.364 (12) |
O1—C7 | 1.450 (13) | O3—C37 | 1.436 (14) |
O2—C14 | 1.199 (13) | O4—C44 | 1.224 (13) |
C1—C2 | 1.527 (17) | C31—C32 | 1.527 (18) |
C1—H1A | 0.9800 | C31—H31A | 0.9800 |
C1—H1B | 0.9800 | C31—H31B | 0.9800 |
C1—H1C | 0.9800 | C31—H31C | 0.9800 |
C2—C3 | 1.526 (15) | C32—C33 | 1.509 (16) |
C2—H2A | 0.9900 | C32—H32A | 0.9900 |
C2—H2B | 0.9900 | C32—H32B | 0.9900 |
C3—C4 | 1.526 (15) | C33—C34 | 1.504 (16) |
C3—H3A | 0.9900 | C33—H33A | 0.9900 |
C3—H3B | 0.9900 | C33—H33B | 0.9900 |
C4—C5 | 1.521 (15) | C34—C35 | 1.504 (15) |
C4—H4A | 0.9900 | C34—H34A | 0.9900 |
C4—H4B | 0.9900 | C34—H34B | 0.9900 |
C5—C6 | 1.518 (16) | C35—C36 | 1.528 (15) |
C5—H5A | 0.9900 | C35—H35A | 0.9900 |
C5—H5B | 0.9900 | C35—H35B | 0.9900 |
C6—C7 | 1.494 (15) | C36—C37 | 1.503 (14) |
C6—H6A | 0.9900 | C36—H36A | 0.9900 |
C6—H6B | 0.9900 | C36—H36B | 0.9900 |
C7—H7A | 0.9900 | C37—H37A | 0.9900 |
C7—H7B | 0.9900 | C37—H37B | 0.9900 |
C8—C13 | 1.379 (15) | C38—C39 | 1.384 (15) |
C8—C9 | 1.406 (15) | C38—C43 | 1.400 (15) |
C9—C10 | 1.368 (14) | C39—C40 | 1.391 (14) |
C9—H9 | 0.9500 | C39—H39 | 0.9500 |
C10—C11 | 1.382 (13) | C40—C41 | 1.402 (15) |
C10—H10 | 0.9500 | C40—H40 | 0.9500 |
C11—C12 | 1.412 (14) | C41—C42 | 1.390 (15) |
C11—C14 | 1.492 (15) | C41—C44 | 1.478 (15) |
C12—C13 | 1.386 (15) | C42—C43 | 1.375 (14) |
C12—H12 | 0.9500 | C42—H42 | 0.9500 |
C13—H13 | 0.9500 | C43—H43 | 0.9500 |
C15—C20 | 1.392 (15) | C45—C46 | 1.375 (14) |
C15—C16 | 1.411 (15) | C45—C50 | 1.399 (15) |
C16—C17 | 1.387 (16) | C46—C47 | 1.399 (15) |
C16—H16 | 0.9500 | C46—H46 | 0.9500 |
C17—C18 | 1.391 (15) | C47—C48 | 1.411 (15) |
C17—H17 | 0.9500 | C47—H47 | 0.9500 |
C18—C19 | 1.401 (15) | C48—C49 | 1.381 (15) |
C18—C21 | 1.504 (16) | C48—C51 | 1.512 (15) |
C19—C20 | 1.400 (15) | C49—C50 | 1.381 (16) |
C19—H19 | 0.9500 | C49—H49 | 0.9500 |
C20—H20 | 0.9500 | C50—H50 | 0.9500 |
C21—C22 | 1.518 (16) | C51—C52 | 1.512 (15) |
C21—H21A | 0.9900 | C51—H51A | 0.9900 |
C21—H21B | 0.9900 | C51—H51B | 0.9900 |
C22—C23 | 1.506 (16) | C52—C53 | 1.519 (16) |
C22—H22A | 0.9900 | C52—H52A | 0.9900 |
C22—H22B | 0.9900 | C52—H52B | 0.9900 |
C23—C24 | 1.518 (17) | C53—C54 | 1.499 (17) |
C23—H23A | 0.9900 | C53—H53A | 0.9900 |
C23—H23B | 0.9900 | C53—H53B | 0.9900 |
C24—C25 | 1.518 (16) | C54—C55 | 1.513 (17) |
C24—H24A | 0.9900 | C54—H54A | 0.9900 |
C24—H24B | 0.9900 | C54—H54B | 0.9900 |
C25—H25A | 0.9800 | C55—H55A | 0.9800 |
C25—H25B | 0.9800 | C55—H55B | 0.9800 |
C25—H25C | 0.9800 | C55—H55C | 0.9800 |
C15—S1—C14 | 103.4 (5) | C45—S2—C44 | 103.0 (5) |
C8—O1—C7 | 118.0 (8) | C38—O3—C37 | 116.9 (8) |
C2—C1—H1A | 109.5 | C32—C31—H31A | 109.5 |
C2—C1—H1B | 109.5 | C32—C31—H31B | 109.5 |
H1A—C1—H1B | 109.5 | H31A—C31—H31B | 109.5 |
C2—C1—H1C | 109.5 | C32—C31—H31C | 109.5 |
H1A—C1—H1C | 109.5 | H31A—C31—H31C | 109.5 |
H1B—C1—H1C | 109.5 | H31B—C31—H31C | 109.5 |
C3—C2—C1 | 111.8 (12) | C33—C32—C31 | 113.8 (12) |
C3—C2—H2A | 109.3 | C33—C32—H32A | 108.8 |
C1—C2—H2A | 109.3 | C31—C32—H32A | 108.8 |
C3—C2—H2B | 109.3 | C33—C32—H32B | 108.8 |
C1—C2—H2B | 109.3 | C31—C32—H32B | 108.8 |
H2A—C2—H2B | 107.9 | H32A—C32—H32B | 107.7 |
C4—C3—C2 | 114.2 (10) | C34—C33—C32 | 116.1 (11) |
C4—C3—H3A | 108.7 | C34—C33—H33A | 108.3 |
C2—C3—H3A | 108.7 | C32—C33—H33A | 108.3 |
C4—C3—H3B | 108.7 | C34—C33—H33B | 108.3 |
C2—C3—H3B | 108.7 | C32—C33—H33B | 108.3 |
H3A—C3—H3B | 107.6 | H33A—C33—H33B | 107.4 |
C5—C4—C3 | 114.1 (10) | C33—C34—C35 | 115.5 (10) |
C5—C4—H4A | 108.7 | C33—C34—H34A | 108.4 |
C3—C4—H4A | 108.7 | C35—C34—H34A | 108.4 |
C5—C4—H4B | 108.7 | C33—C34—H34B | 108.4 |
C3—C4—H4B | 108.7 | C35—C34—H34B | 108.4 |
H4A—C4—H4B | 107.6 | H34A—C34—H34B | 107.5 |
C6—C5—C4 | 112.4 (10) | C34—C35—C36 | 114.8 (10) |
C6—C5—H5A | 109.1 | C34—C35—H35A | 108.6 |
C4—C5—H5A | 109.1 | C36—C35—H35A | 108.6 |
C6—C5—H5B | 109.1 | C34—C35—H35B | 108.6 |
C4—C5—H5B | 109.1 | C36—C35—H35B | 108.6 |
H5A—C5—H5B | 107.9 | H35A—C35—H35B | 107.6 |
C7—C6—C5 | 112.5 (10) | C37—C36—C35 | 111.8 (10) |
C7—C6—H6A | 109.1 | C37—C36—H36A | 109.3 |
C5—C6—H6A | 109.1 | C35—C36—H36A | 109.3 |
C7—C6—H6B | 109.1 | C37—C36—H36B | 109.3 |
C5—C6—H6B | 109.1 | C35—C36—H36B | 109.3 |
H6A—C6—H6B | 107.8 | H36A—C36—H36B | 107.9 |
O1—C7—C6 | 108.0 (10) | O3—C37—C36 | 107.2 (9) |
O1—C7—H7A | 110.1 | O3—C37—H37A | 110.3 |
C6—C7—H7A | 110.1 | C36—C37—H37A | 110.3 |
O1—C7—H7B | 110.1 | O3—C37—H37B | 110.3 |
C6—C7—H7B | 110.1 | C36—C37—H37B | 110.3 |
H7A—C7—H7B | 108.4 | H37A—C37—H37B | 108.5 |
O1—C8—C13 | 125.5 (10) | O3—C38—C39 | 125.2 (10) |
O1—C8—C9 | 115.2 (9) | O3—C38—C43 | 114.8 (9) |
C13—C8—C9 | 119.2 (10) | C39—C38—C43 | 120.0 (10) |
C10—C9—C8 | 120.1 (9) | C38—C39—C40 | 119.7 (10) |
C10—C9—H9 | 119.9 | C38—C39—H39 | 120.2 |
C8—C9—H9 | 119.9 | C40—C39—H39 | 120.2 |
C9—C10—C11 | 121.6 (9) | C39—C40—C41 | 120.7 (10) |
C9—C10—H10 | 119.2 | C39—C40—H40 | 119.6 |
C11—C10—H10 | 119.2 | C41—C40—H40 | 119.6 |
C10—C11—C12 | 118.1 (10) | C42—C41—C40 | 118.5 (11) |
C10—C11—C14 | 124.1 (9) | C42—C41—C44 | 123.1 (10) |
C12—C11—C14 | 117.8 (9) | C40—C41—C44 | 118.5 (9) |
C13—C12—C11 | 120.5 (9) | C43—C42—C41 | 121.3 (10) |
C13—C12—H12 | 119.8 | C43—C42—H42 | 119.4 |
C11—C12—H12 | 119.8 | C41—C42—H42 | 119.4 |
C8—C13—C12 | 120.3 (10) | C42—C43—C38 | 119.8 (10) |
C8—C13—H13 | 119.8 | C42—C43—H43 | 120.1 |
C12—C13—H13 | 119.8 | C38—C43—H43 | 120.1 |
O2—C14—C11 | 124.1 (9) | O4—C44—C41 | 124.4 (10) |
O2—C14—S1 | 123.1 (9) | O4—C44—S2 | 122.0 (9) |
C11—C14—S1 | 112.7 (7) | C41—C44—S2 | 113.4 (7) |
C20—C15—C16 | 118.9 (10) | C46—C45—C50 | 118.8 (10) |
C20—C15—S1 | 122.2 (9) | C46—C45—S2 | 122.8 (8) |
C16—C15—S1 | 118.9 (8) | C50—C45—S2 | 118.1 (8) |
C17—C16—C15 | 119.5 (10) | C45—C46—C47 | 121.2 (10) |
C17—C16—H16 | 120.2 | C45—C46—H46 | 119.4 |
C15—C16—H16 | 120.2 | C47—C46—H46 | 119.4 |
C16—C17—C18 | 122.4 (10) | C46—C47—C48 | 120.1 (10) |
C16—C17—H17 | 118.8 | C46—C47—H47 | 119.9 |
C18—C17—H17 | 118.8 | C48—C47—H47 | 119.9 |
C17—C18—C19 | 117.6 (11) | C49—C48—C47 | 117.5 (10) |
C17—C18—C21 | 120.2 (10) | C49—C48—C51 | 120.4 (10) |
C19—C18—C21 | 122.2 (10) | C47—C48—C51 | 122.1 (10) |
C20—C19—C18 | 121.1 (10) | C48—C49—C50 | 122.4 (10) |
C20—C19—H19 | 119.4 | C48—C49—H49 | 118.8 |
C18—C19—H19 | 119.4 | C50—C49—H49 | 118.8 |
C15—C20—C19 | 120.3 (11) | C49—C50—C45 | 119.9 (10) |
C15—C20—H20 | 119.8 | C49—C50—H50 | 120.0 |
C19—C20—H20 | 119.8 | C45—C50—H50 | 120.0 |
C18—C21—C22 | 117.4 (10) | C48—C51—C52 | 117.9 (10) |
C18—C21—H21A | 107.9 | C48—C51—H51A | 107.8 |
C22—C21—H21A | 107.9 | C52—C51—H51A | 107.8 |
C18—C21—H21B | 107.9 | C48—C51—H51B | 107.8 |
C22—C21—H21B | 107.9 | C52—C51—H51B | 107.8 |
H21A—C21—H21B | 107.2 | H51A—C51—H51B | 107.2 |
C23—C22—C21 | 114.2 (10) | C51—C52—C53 | 113.7 (10) |
C23—C22—H22A | 108.7 | C51—C52—H52A | 108.8 |
C21—C22—H22A | 108.7 | C53—C52—H52A | 108.8 |
C23—C22—H22B | 108.7 | C51—C52—H52B | 108.8 |
C21—C22—H22B | 108.7 | C53—C52—H52B | 108.8 |
H22A—C22—H22B | 107.6 | H52A—C52—H52B | 107.7 |
C22—C23—C24 | 114.1 (11) | C54—C53—C52 | 114.0 (11) |
C22—C23—H23A | 108.7 | C54—C53—H53A | 108.8 |
C24—C23—H23A | 108.7 | C52—C53—H53A | 108.8 |
C22—C23—H23B | 108.7 | C54—C53—H53B | 108.8 |
C24—C23—H23B | 108.7 | C52—C53—H53B | 108.8 |
H23A—C23—H23B | 107.6 | H53A—C53—H53B | 107.7 |
C23—C24—C25 | 114.6 (12) | C53—C54—C55 | 115.3 (12) |
C23—C24—H24A | 108.6 | C53—C54—H54A | 108.5 |
C25—C24—H24A | 108.6 | C55—C54—H54A | 108.5 |
C23—C24—H24B | 108.6 | C53—C54—H54B | 108.5 |
C25—C24—H24B | 108.6 | C55—C54—H54B | 108.5 |
H24A—C24—H24B | 107.6 | H54A—C54—H54B | 107.5 |
C24—C25—H25A | 109.5 | C54—C55—H55A | 109.5 |
C24—C25—H25B | 109.5 | C54—C55—H55B | 109.5 |
H25A—C25—H25B | 109.5 | H55A—C55—H55B | 109.5 |
C24—C25—H25C | 109.5 | C54—C55—H55C | 109.5 |
H25A—C25—H25C | 109.5 | H55A—C55—H55C | 109.5 |
H25B—C25—H25C | 109.5 | H55B—C55—H55C | 109.5 |
C1—C2—C3—C4 | 179.4 (12) | C31—C32—C33—C34 | −179.3 (12) |
C2—C3—C4—C5 | −178.6 (11) | C32—C33—C34—C35 | −177.9 (11) |
C3—C4—C5—C6 | −178.3 (11) | C33—C34—C35—C36 | −179.4 (10) |
C4—C5—C6—C7 | −175.8 (11) | C34—C35—C36—C37 | −179.1 (10) |
C8—O1—C7—C6 | −176.4 (9) | C38—O3—C37—C36 | −177.0 (9) |
C5—C6—C7—O1 | −175.5 (10) | C35—C36—C37—O3 | −177.9 (9) |
C7—O1—C8—C13 | −5.4 (16) | C37—O3—C38—C39 | −1.6 (16) |
C7—O1—C8—C9 | 177.1 (10) | C37—O3—C38—C43 | 177.7 (9) |
O1—C8—C9—C10 | −178.1 (9) | O3—C38—C39—C40 | 177.2 (9) |
C13—C8—C9—C10 | 4.3 (16) | C43—C38—C39—C40 | −2.1 (15) |
C8—C9—C10—C11 | −4.1 (17) | C38—C39—C40—C41 | 1.8 (14) |
C9—C10—C11—C12 | 2.6 (17) | C39—C40—C41—C42 | −1.8 (15) |
C9—C10—C11—C14 | −178.0 (10) | C39—C40—C41—C44 | 178.9 (9) |
C10—C11—C12—C13 | −1.4 (16) | C40—C41—C42—C43 | 2.3 (15) |
C14—C11—C12—C13 | 179.2 (10) | C44—C41—C42—C43 | −178.4 (9) |
O1—C8—C13—C12 | 179.5 (10) | C41—C42—C43—C38 | −2.7 (15) |
C9—C8—C13—C12 | −3.1 (17) | O3—C38—C43—C42 | −176.8 (9) |
C11—C12—C13—C8 | 1.7 (16) | C39—C38—C43—C42 | 2.6 (15) |
C10—C11—C14—O2 | 178.2 (11) | C42—C41—C44—O4 | 178.5 (11) |
C12—C11—C14—O2 | −2.4 (16) | C40—C41—C44—O4 | −2.3 (15) |
C10—C11—C14—S1 | −0.6 (14) | C42—C41—C44—S2 | 2.1 (13) |
C12—C11—C14—S1 | 178.8 (8) | C40—C41—C44—S2 | −178.6 (8) |
C15—S1—C14—O2 | 4.2 (11) | C45—S2—C44—O4 | 4.8 (11) |
C15—S1—C14—C11 | −177.0 (8) | C45—S2—C44—C41 | −178.8 (7) |
C14—S1—C15—C20 | 54.8 (11) | C44—S2—C45—C46 | 58.3 (11) |
C14—S1—C15—C16 | −125.2 (9) | C44—S2—C45—C50 | −127.1 (9) |
C20—C15—C16—C17 | 5.3 (16) | C50—C45—C46—C47 | −0.2 (17) |
S1—C15—C16—C17 | −174.7 (8) | S2—C45—C46—C47 | 174.3 (8) |
C15—C16—C17—C18 | −2.6 (16) | C45—C46—C47—C48 | 0.2 (17) |
C16—C17—C18—C19 | 0.0 (16) | C46—C47—C48—C49 | −0.7 (17) |
C16—C17—C18—C21 | 180.0 (10) | C46—C47—C48—C51 | 178.6 (11) |
C17—C18—C19—C20 | −0.1 (17) | C47—C48—C49—C50 | 1.2 (18) |
C21—C18—C19—C20 | 179.9 (11) | C51—C48—C49—C50 | −178.1 (11) |
C16—C15—C20—C19 | −5.5 (17) | C48—C49—C50—C45 | −1.3 (17) |
S1—C15—C20—C19 | 174.5 (9) | C46—C45—C50—C49 | 0.8 (17) |
C18—C19—C20—C15 | 3.0 (18) | S2—C45—C50—C49 | −174.1 (9) |
C17—C18—C21—C22 | −178.4 (10) | C49—C48—C51—C52 | 179.3 (11) |
C19—C18—C21—C22 | 1.6 (16) | C47—C48—C51—C52 | 0.0 (17) |
C18—C21—C22—C23 | −174.9 (10) | C48—C51—C52—C53 | −177.6 (11) |
C21—C22—C23—C24 | −179.9 (11) | C51—C52—C53—C54 | −177.3 (12) |
C22—C23—C24—C25 | 180.0 (12) | C52—C53—C54—C55 | 179.7 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O3i | 0.95 | 2.58 | 3.377 (13) | 141 |
C16—H16···O2ii | 0.95 | 2.47 | 3.355 (13) | 154 |
C20—H20···S2iii | 0.95 | 2.74 | 3.538 (13) | 142 |
C50—H50···O4ii | 0.95 | 2.57 | 3.429 (14) | 151 |
C7—H7A···O4 | 0.99 | 2.68 | 3.508 (15) | 141 |
C37—H37A···O2iv | 0.99 | 2.67 | 3.461 (16) | 137 |
Symmetry codes: (i) −x+3/2, y+1, z+1/2; (ii) x, y+1, z; (iii) −x+3/2, y, z+1/2; (iv) x, y−1, z. |
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