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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1336.
Published online 2010 May 15. doi:  10.1107/S1600536810016661
PMCID: PMC2979557

5,22-Stigmastadien-3β-yl p-toluene­sulfonate

Abstract

The asymmetric unit of the title compound {systematic name: (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methyl­hept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodeca­hydro-1H-cyclo­penta­[a]phenanthren-3-yl p-toluene­sulfonate}, C36H54O3S, comprises two independent mol­ecules that differ significantly in terms of the relative orientations of the peripheral groups; the conformation about the C=C bond of the side chain is E. In the crystal, mol­ecules associate into linear supra­molecular chains aligned along the a axis via C—H(...)O inter­actions.

Related literature

For the use of 5,22-stigmastadien-3β-yl p-toluene­sulfonate, see: Partridge et al. (1974 [triangle]); Khripach et al. (2002 [triangle]); Foley et al. (2010 [triangle]); Ketuly et al. (1997 [triangle]). For the synthesis, see: Foley et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1336-scheme1.jpg

Experimental

Crystal data

  • C36H54O3S
  • M r = 566.86
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1336-efi1.jpg
  • a = 7.0361 (1) Å
  • b = 11.2350 (1) Å
  • c = 21.1550 (2) Å
  • α = 90.777 (1)°
  • β = 96.166 (1)°
  • γ = 101.153 (1)°
  • V = 1630.23 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 100 K
  • 0.49 × 0.37 × 0.27 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.669, T max = 0.746
  • 15647 measured reflections
  • 13115 independent reflections
  • 12382 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.089
  • S = 1.02
  • 13115 reflections
  • 735 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.37 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 5643 Friedel pairs
  • Flack parameter: 0.02 (4)

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]), DIAMOND (Brandenburg, 2006 [triangle]) and Qmol (Gans & Shalloway, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016661/hb5438sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016661/hb5438Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The title compound, (I), a stigmasterol tosylate, has been used as a precursor for the synthesis of cholesterol and other sterols with variable side-chains (Partridge et al. 1974; Khripach et al. 2002; Foley et al. 2010) and for the determination of absolute configuration (Ketuly et al. 1997). Herein, (I) has been characterised by crystallography and shown to crystallise with two independent molecules in the crystallographic asymmetric unit, Figs 1 and 2. While the central steroid residues in the independent molecules are virtually superimposable, as seen from Fig. 3, the peripheral groups have quite different orientations. These differences are quantified in the values of the C5–S1–O1–C8 and C38–S2–O4–C41 torsion angles of 67.92 (13) and -63.53 (14) °, respectively, which indicate that the tosylate groups lie to either side of the respective molecule. The differences in the orientation of the terminal iso-propyl group are best quantified in the C27–C28–C29–C30, C31 torsion angles of 45.2 (2) and 168.45 (16) °, respectively, compared with 58.2 (2) and -66.8 (2) ° for C60–C61–C62–C63,C64, respectively. The conformation about the C═C [C26═C27 = 1.322 (3) Å and C59═C60 = 1.324 (2) Å] double bond of the side-chain in each molecule is E.

In the crystal structure, the molecules associate into linear supramolecular chains aligned along the a axis mediated by C–H···O interactions, Fig. 2 and Table 1. The chains inter-digitate along the b axis as shown in Fig. 5.

Experimental

Stigmasterol (40 g, 97 mmol) was dissolved in dried and redistilled pyridine (250 ml) and p-toluenesulfonyl chloride (30 g, 157.4 mmol) added, and the solution was then stirred at room temperature for 28 h. The reaction mixture was mixed with 5% aqueous sodium bicarbonate and the solid precipitate filtered, washed with water, dried at room temperature, and recovered (52 g). The crude product was recrystallized from acetone, yielding fine crystals of stigmasterol tosylate (45.8 g), m.pt. 407–410 K. The compound was further recrystallised and colourless blocks of (I) were grown from n-hexane:carbon tetrachloride (1/1), m.pt. 415–417 K [Lit. 415–417 K (Foley et al. , 2010)].

Refinement

The H atoms were geometrically placed (C–H = 0.95–1.00 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of the first independent molecule in (I) displacement ellipsoids at the 50% probability level.
Fig. 2.
The molecular structure of the second independent molecule in (I) showing displacement ellipsoids at the 50% probability level.
Fig. 3.
Overlap diagram highlighting the different conformations of the first (red) and second (blue) independent molecules in (I).
Fig. 4.
A view of a supramolecular chain in (I) aligned along the a axis. The C–H···O contacts are shown as orange dashed lines. Colour code: O, red; C, grey; and H, green.
Fig. 5.
A view in projection down the a axis of the unit cell contents in (I) showing the inter-digitation of supramolecular chains. The C–H···O contacts are shown as orange dashed lines, respectively. Colour code: O, red; C, grey; ...

Crystal data

C36H54O3SZ = 2
Mr = 566.86F(000) = 620
Triclinic, P1Dx = 1.155 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0361 (1) ÅCell parameters from 8182 reflections
b = 11.2350 (1) Åθ = 2.6–30.5°
c = 21.1550 (2) ŵ = 0.13 mm1
α = 90.777 (1)°T = 100 K
β = 96.166 (1)°Block, colourless
γ = 101.153 (1)°0.49 × 0.37 × 0.27 mm
V = 1630.23 (3) Å3

Data collection

Bruker SMART APEX CCD diffractometer13115 independent reflections
Radiation source: fine-focus sealed tube12382 reflections with I > 2σ(I)
graphiteRint = 0.018
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.669, Tmax = 0.746k = −14→14
15647 measured reflectionsl = −27→27

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.089w = 1/[σ2(Fo2) + (0.049P)2 + 0.2642P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
13115 reflectionsΔρmax = 0.35 e Å3
735 parametersΔρmin = −0.37 e Å3
3 restraintsAbsolute structure: Flack (1983), 5643 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (4)

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.69443 (5)0.84972 (3)0.44298 (2)0.01550 (9)
O10.67495 (19)0.97242 (11)0.47537 (6)0.0185 (3)
O20.62261 (19)0.85861 (12)0.37793 (6)0.0202 (3)
O30.88690 (18)0.82684 (12)0.45847 (6)0.0213 (3)
C10.1261 (3)0.48353 (19)0.57090 (10)0.0283 (5)
H1A0.14840.50090.61690.042*
H1B0.14500.40110.56190.042*
H1C−0.00740.49030.55510.042*
C20.2679 (3)0.57305 (17)0.53824 (9)0.0208 (4)
C30.4643 (3)0.56629 (17)0.54289 (9)0.0190 (4)
H30.50880.50340.56630.023*
C40.5962 (3)0.65025 (16)0.51380 (8)0.0174 (4)
H40.73010.64520.51720.021*
C50.5300 (3)0.74157 (16)0.47974 (8)0.0155 (3)
C60.3344 (3)0.74989 (18)0.47399 (10)0.0214 (4)
H60.29030.81250.45030.026*
C70.2052 (3)0.66572 (18)0.50327 (10)0.0240 (4)
H70.07130.67090.49960.029*
C80.7474 (3)0.99334 (17)0.54366 (8)0.0172 (4)
H80.78880.91890.56110.021*
C90.9196 (3)1.09800 (17)0.54931 (9)0.0206 (4)
H9A0.88141.16930.52820.025*
H9B1.02631.07540.52780.025*
C100.9908 (3)1.13062 (17)0.61942 (9)0.0193 (4)
H10A1.09691.20320.62200.023*
H10B1.04671.06300.63820.023*
C110.8321 (3)1.15659 (15)0.66011 (8)0.0171 (4)
C11A0.7752 (3)1.27858 (16)0.64174 (9)0.0223 (4)
H11A0.73401.27680.59590.034*
H11B0.88781.34480.65240.034*
H11C0.66781.29170.66520.034*
C120.6484 (3)1.05841 (16)0.64686 (9)0.0172 (4)
C130.5805 (3)1.02109 (17)0.57757 (9)0.0198 (4)
H13A0.47480.94830.57520.024*
H13B0.52771.08740.55610.024*
C140.5425 (3)1.01280 (16)0.69279 (8)0.0192 (3)
H140.43070.95130.68080.023*
C150.5868 (3)1.05133 (16)0.76192 (8)0.0190 (3)
H15A0.62300.98290.78630.023*
H15B0.46751.06970.77750.023*
C160.7520 (3)1.16293 (15)0.77506 (8)0.0162 (3)
H160.69781.23740.76520.019*
C170.9115 (3)1.15600 (16)0.73162 (8)0.0161 (3)
H170.94781.07490.73830.019*
C181.0995 (3)1.25072 (17)0.74971 (9)0.0205 (4)
H18A1.07681.33110.73590.025*
H18B1.20351.23010.72610.025*
C191.1718 (3)1.26021 (17)0.82118 (9)0.0204 (4)
H19A1.21661.18480.83390.024*
H19B1.28431.32870.82950.024*
C201.0109 (3)1.27989 (15)0.86124 (8)0.0162 (3)
C20A0.9540 (3)1.40312 (16)0.84761 (9)0.0226 (4)
H20A1.06931.46800.85650.034*
H20B0.85481.41580.87480.034*
H20C0.90161.40410.80280.034*
C210.8384 (3)1.17209 (16)0.84454 (8)0.0167 (3)
H210.89241.09690.85230.020*
C220.7035 (3)1.17900 (18)0.89584 (9)0.0234 (4)
H22A0.62701.09770.90320.028*
H22B0.61271.23420.88380.028*
C230.8437 (3)1.22925 (17)0.95564 (9)0.0217 (4)
H23A0.84211.16650.98810.026*
H23B0.80381.30070.97420.026*
C241.0514 (3)1.26601 (17)0.93432 (9)0.0172 (4)
H241.11801.19550.94120.021*
C251.1738 (3)1.37487 (16)0.97497 (8)0.0210 (4)
H251.11001.44630.96700.025*
C25A1.3849 (3)1.4103 (2)0.95873 (10)0.0347 (5)
H25A1.45601.47740.98730.052*
H25B1.38441.43570.91460.052*
H25C1.44881.34030.96400.052*
C261.1761 (3)1.34890 (17)1.04477 (9)0.0207 (4)
H261.23461.28381.05990.025*
C271.1020 (3)1.41072 (16)1.08631 (9)0.0188 (4)
H271.03901.47311.06990.023*
C281.1069 (3)1.39278 (16)1.15671 (8)0.0198 (4)
H281.16681.32061.16700.024*
C290.9004 (3)1.36906 (17)1.17799 (8)0.0216 (4)
H290.85341.44761.17670.026*
C300.7557 (3)1.2771 (2)1.13373 (10)0.0328 (5)
H30A0.80601.20211.13020.049*
H30B0.73841.31091.09150.049*
H30C0.63001.25941.15110.049*
C310.8994 (3)1.3254 (2)1.24636 (10)0.0323 (5)
H31A0.77001.32251.26010.048*
H31B0.99671.38181.27460.048*
H31C0.93091.24421.24810.048*
C321.2370 (3)1.50536 (19)1.19232 (9)0.0277 (4)
H32A1.18361.57801.17990.033*
H32B1.23071.49641.23860.033*
C331.4489 (3)1.5262 (3)1.17963 (12)0.0451 (6)
H33A1.50611.45741.19460.068*
H33B1.52071.60091.20220.068*
H33C1.45681.53381.13390.068*
S20.30849 (5)1.27220 (3)0.44943 (2)0.01603 (9)
O40.32421 (19)1.14814 (11)0.41769 (6)0.0179 (3)
O50.11769 (19)1.29670 (12)0.43282 (6)0.0219 (3)
O60.3765 (2)1.26274 (12)0.51495 (6)0.0215 (3)
C340.8898 (3)1.64290 (19)0.32767 (10)0.0264 (4)
H34A1.00671.67060.35770.040*
H34B0.83161.71250.31470.040*
H34C0.92551.60410.29010.040*
C350.7448 (3)1.55291 (17)0.35912 (9)0.0203 (4)
C360.5459 (3)1.55371 (17)0.34939 (9)0.0198 (4)
H360.50151.61390.32380.024*
C370.4116 (3)1.46780 (17)0.37652 (9)0.0182 (4)
H370.27641.46900.36950.022*
C380.4769 (3)1.38034 (16)0.41391 (9)0.0164 (4)
C390.6743 (3)1.37796 (17)0.42510 (9)0.0192 (4)
H390.71821.31830.45120.023*
C400.8067 (3)1.46471 (18)0.39740 (9)0.0213 (4)
H400.94191.46370.40480.026*
C410.2679 (3)1.12867 (16)0.34818 (8)0.0170 (4)
H410.21721.20010.33060.020*
C420.4461 (3)1.11455 (17)0.31752 (9)0.0179 (4)
H42A0.50071.04670.33660.021*
H42B0.54671.18970.32500.021*
C430.3909 (3)1.08909 (16)0.24600 (9)0.0179 (4)
H43A0.50851.07800.22660.022*
H43B0.34801.16100.22710.022*
C440.2286 (2)0.97669 (16)0.22859 (8)0.0154 (3)
C44A0.3072 (3)0.86021 (16)0.24517 (9)0.0183 (4)
H44A0.42140.85810.22270.027*
H44B0.20570.78880.23210.027*
H44C0.34430.86000.29120.027*
C450.0589 (3)0.98035 (16)0.26753 (8)0.0160 (3)
C460.1093 (3)1.01536 (17)0.33770 (9)0.0193 (4)
H46A0.15380.94750.36040.023*
H46B−0.00881.03000.35560.023*
C47−0.1263 (2)0.94840 (16)0.24258 (8)0.0195 (4)
H47−0.22390.95350.26970.023*
C48−0.1933 (3)0.90488 (18)0.17491 (9)0.0224 (4)
H48A−0.25610.96670.15270.027*
H48B−0.29280.82930.17480.027*
C49−0.0279 (2)0.88027 (17)0.13799 (8)0.0169 (4)
H490.00210.79950.14990.020*
C500.1550 (2)0.97888 (16)0.15671 (8)0.0152 (3)
H500.11381.05860.15020.018*
C510.3161 (3)0.97594 (17)0.11341 (8)0.0195 (4)
H51A0.37520.90430.12340.023*
H51B0.41921.04930.12310.023*
C520.2445 (3)0.97042 (16)0.04174 (8)0.0192 (4)
H52A0.20081.04670.03010.023*
H52B0.35340.96270.01700.023*
C530.0754 (2)0.86221 (15)0.02491 (8)0.0154 (3)
C53A0.1438 (3)0.74110 (16)0.03621 (9)0.0198 (4)
H53A0.18510.73510.08160.030*
H53B0.25360.73780.01180.030*
H53C0.03630.67340.02240.030*
C54−0.0868 (2)0.87808 (16)0.06625 (8)0.0175 (4)
H54−0.11780.95960.05660.021*
C55−0.2647 (3)0.78459 (19)0.03754 (9)0.0265 (4)
H55A−0.38730.81120.04440.032*
H55B−0.26560.70440.05650.032*
C56−0.2399 (3)0.77885 (19)−0.03430 (9)0.0254 (4)
H56A−0.34470.8107−0.05950.030*
H56B−0.24560.6940−0.04890.030*
C57−0.0379 (3)0.85800 (17)−0.04245 (9)0.0179 (4)
H57−0.05870.9421−0.05120.021*
C580.0537 (3)0.81453 (16)−0.09941 (8)0.0186 (3)
H580.07520.7303−0.09150.022*
C58A0.2503 (3)0.89545 (18)−0.10828 (9)0.0248 (4)
H58A0.29190.8736−0.14890.037*
H58B0.34780.8838−0.07340.037*
H58C0.23700.9807−0.10820.037*
C59−0.0795 (3)0.81142 (16)−0.16047 (8)0.0195 (4)
H59−0.11950.8850−0.17210.023*
C60−0.1459 (3)0.71560 (17)−0.19935 (9)0.0189 (4)
H60−0.11820.6399−0.18570.023*
C61−0.2616 (3)0.71673 (16)−0.26345 (9)0.0207 (4)
H61−0.27840.8022−0.27030.025*
C62−0.4672 (3)0.63669 (18)−0.26825 (10)0.0252 (4)
H62−0.53540.6497−0.31080.030*
C63−0.5848 (3)0.6760 (2)−0.21817 (11)0.0367 (5)
H63A−0.71940.6306−0.22540.055*
H63B−0.58390.7631−0.22110.055*
H63C−0.52680.6595−0.17580.055*
C64−0.4669 (3)0.50155 (19)−0.26452 (12)0.0360 (5)
H64A−0.40800.4846−0.22230.054*
H64B−0.39120.4774−0.29710.054*
H64C−0.60110.4556−0.27180.054*
C65−0.1447 (3)0.68280 (19)−0.31588 (9)0.0284 (4)
H65A−0.09750.6076−0.30440.034*
H65B−0.23230.6655−0.35620.034*
C660.0285 (3)0.7812 (2)−0.32658 (10)0.0336 (5)
H66A−0.01700.8557−0.33870.050*
H66B0.09620.7544−0.36070.050*
H66C0.11830.7971−0.28730.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0165 (2)0.0165 (2)0.0130 (2)0.00202 (16)0.00175 (15)0.00057 (16)
O10.0251 (7)0.0152 (6)0.0144 (7)0.0033 (5)−0.0008 (5)0.0006 (5)
O20.0240 (7)0.0214 (7)0.0139 (7)0.0021 (5)0.0004 (5)0.0000 (5)
O30.0172 (7)0.0258 (7)0.0209 (7)0.0030 (5)0.0039 (5)0.0028 (6)
C10.0279 (11)0.0257 (10)0.0296 (11)−0.0027 (8)0.0108 (9)0.0005 (9)
C20.0235 (10)0.0180 (9)0.0194 (10)−0.0013 (7)0.0056 (8)−0.0040 (7)
C30.0246 (10)0.0154 (9)0.0165 (9)0.0023 (7)0.0026 (7)−0.0002 (7)
C40.0179 (9)0.0180 (9)0.0160 (9)0.0037 (7)0.0009 (7)−0.0007 (7)
C50.0164 (9)0.0157 (8)0.0138 (9)0.0008 (7)0.0027 (7)−0.0001 (7)
C60.0155 (9)0.0222 (10)0.0267 (10)0.0047 (7)0.0007 (7)0.0030 (8)
C70.0142 (9)0.0255 (10)0.0320 (11)0.0027 (7)0.0033 (8)0.0000 (8)
C80.0215 (9)0.0165 (9)0.0120 (9)0.0006 (7)−0.0001 (7)0.0002 (7)
C90.0237 (10)0.0206 (9)0.0149 (9)−0.0023 (7)0.0029 (7)−0.0007 (7)
C100.0208 (9)0.0180 (9)0.0166 (9)−0.0026 (7)0.0031 (7)−0.0013 (7)
C110.0198 (9)0.0130 (8)0.0161 (9)−0.0013 (7)0.0001 (7)0.0012 (6)
C11A0.0281 (10)0.0172 (9)0.0202 (9)0.0015 (7)0.0013 (7)0.0008 (7)
C120.0188 (9)0.0156 (8)0.0167 (9)0.0033 (7)0.0005 (7)−0.0010 (7)
C130.0212 (9)0.0178 (9)0.0182 (9)−0.0008 (7)0.0008 (7)0.0000 (7)
C140.0173 (8)0.0190 (8)0.0194 (9)−0.0007 (6)0.0008 (7)−0.0024 (7)
C150.0176 (9)0.0210 (8)0.0174 (9)0.0004 (7)0.0042 (7)−0.0006 (7)
C160.0151 (8)0.0152 (8)0.0171 (9)0.0007 (6)0.0011 (7)−0.0007 (6)
C170.0174 (9)0.0153 (8)0.0149 (8)0.0005 (6)0.0029 (7)0.0006 (6)
C180.0199 (9)0.0216 (9)0.0169 (9)−0.0035 (7)0.0025 (7)−0.0006 (7)
C190.0188 (9)0.0226 (9)0.0176 (9)−0.0004 (7)0.0008 (7)−0.0006 (7)
C200.0179 (9)0.0147 (8)0.0149 (9)0.0015 (7)0.0004 (7)−0.0002 (6)
C20A0.0284 (10)0.0172 (8)0.0210 (9)0.0051 (7)−0.0033 (7)−0.0003 (7)
C210.0181 (9)0.0171 (8)0.0149 (8)0.0028 (7)0.0031 (7)0.0004 (6)
C220.0212 (9)0.0288 (10)0.0183 (9)−0.0005 (7)0.0046 (7)−0.0043 (7)
C230.0228 (9)0.0242 (9)0.0172 (9)0.0019 (7)0.0040 (7)−0.0014 (7)
C240.0184 (9)0.0174 (9)0.0159 (9)0.0041 (7)0.0009 (7)0.0001 (7)
C250.0217 (9)0.0216 (9)0.0184 (9)0.0015 (7)0.0015 (7)−0.0034 (7)
C25A0.0263 (11)0.0478 (13)0.0241 (11)−0.0071 (9)0.0037 (8)−0.0120 (9)
C260.0203 (9)0.0213 (9)0.0193 (9)0.0044 (7)−0.0033 (7)−0.0012 (7)
C270.0191 (9)0.0178 (9)0.0178 (9)0.0015 (7)−0.0011 (7)0.0007 (7)
C280.0227 (9)0.0193 (8)0.0178 (9)0.0055 (7)0.0019 (7)−0.0007 (7)
C290.0235 (9)0.0222 (9)0.0178 (9)0.0015 (7)0.0021 (7)0.0002 (7)
C300.0290 (11)0.0367 (11)0.0269 (11)−0.0078 (9)0.0038 (8)−0.0029 (9)
C310.0363 (12)0.0353 (11)0.0225 (10)−0.0018 (9)0.0065 (9)0.0018 (8)
C320.0286 (11)0.0327 (11)0.0194 (10)0.0001 (8)0.0027 (8)−0.0040 (8)
C330.0288 (12)0.0666 (17)0.0329 (13)−0.0074 (11)0.0047 (10)−0.0145 (11)
S20.0179 (2)0.0153 (2)0.0151 (2)0.00321 (16)0.00275 (16)−0.00007 (16)
O40.0229 (7)0.0170 (6)0.0137 (6)0.0044 (5)0.0004 (5)−0.0008 (5)
O50.0204 (7)0.0202 (7)0.0262 (8)0.0048 (5)0.0056 (6)0.0024 (6)
O60.0286 (7)0.0208 (7)0.0151 (7)0.0042 (6)0.0031 (5)−0.0006 (5)
C340.0282 (11)0.0248 (10)0.0256 (11)0.0006 (8)0.0090 (8)0.0007 (8)
C350.0239 (10)0.0187 (9)0.0175 (9)0.0008 (7)0.0046 (7)−0.0046 (7)
C360.0256 (10)0.0189 (9)0.0144 (9)0.0045 (7)0.0001 (7)0.0000 (7)
C370.0185 (9)0.0198 (9)0.0160 (9)0.0051 (7)−0.0003 (7)−0.0033 (7)
C380.0201 (9)0.0137 (8)0.0145 (9)0.0010 (7)0.0033 (7)−0.0018 (7)
C390.0206 (9)0.0179 (9)0.0198 (9)0.0065 (7)0.0008 (7)−0.0001 (7)
C400.0175 (9)0.0216 (9)0.0246 (10)0.0038 (7)0.0031 (7)−0.0032 (7)
C410.0195 (9)0.0169 (9)0.0135 (9)0.0028 (7)−0.0018 (7)−0.0004 (7)
C420.0167 (9)0.0183 (9)0.0170 (9)−0.0006 (7)0.0019 (7)−0.0013 (7)
C430.0145 (9)0.0194 (9)0.0185 (9)−0.0001 (7)0.0019 (7)−0.0015 (7)
C440.0156 (8)0.0173 (8)0.0131 (8)0.0031 (7)0.0006 (6)−0.0005 (6)
C44A0.0183 (9)0.0186 (8)0.0178 (9)0.0050 (7)−0.0016 (7)−0.0005 (7)
C450.0175 (9)0.0144 (8)0.0158 (9)0.0012 (6)0.0040 (7)−0.0003 (6)
C460.0191 (9)0.0198 (9)0.0185 (9)0.0007 (7)0.0051 (7)0.0017 (7)
C470.0154 (8)0.0242 (9)0.0190 (9)0.0022 (7)0.0061 (7)−0.0020 (7)
C480.0131 (8)0.0319 (10)0.0207 (9)0.0010 (7)0.0023 (7)−0.0028 (7)
C490.0119 (8)0.0222 (9)0.0159 (9)0.0024 (7)0.0011 (6)−0.0007 (7)
C500.0134 (8)0.0159 (8)0.0154 (9)0.0015 (6)−0.0001 (6)0.0000 (6)
C510.0136 (9)0.0252 (9)0.0175 (9)−0.0019 (7)0.0019 (7)−0.0019 (7)
C520.0200 (9)0.0199 (9)0.0158 (9)−0.0012 (7)0.0032 (7)−0.0015 (7)
C530.0139 (8)0.0166 (8)0.0143 (8)0.0010 (6)−0.0007 (6)0.0010 (6)
C53A0.0207 (9)0.0207 (9)0.0187 (9)0.0071 (7)0.0006 (7)0.0013 (7)
C540.0133 (8)0.0206 (9)0.0178 (9)0.0034 (7)−0.0012 (7)−0.0009 (7)
C550.0152 (9)0.0408 (11)0.0201 (9)−0.0015 (8)−0.0006 (7)−0.0052 (8)
C560.0163 (9)0.0367 (11)0.0209 (10)0.0025 (8)−0.0019 (7)−0.0050 (8)
C570.0181 (9)0.0197 (9)0.0154 (9)0.0054 (7)−0.0024 (7)−0.0019 (7)
C580.0214 (9)0.0181 (8)0.0167 (9)0.0067 (7)−0.0005 (7)−0.0026 (6)
C58A0.0224 (10)0.0318 (10)0.0189 (9)0.0017 (8)0.0033 (7)−0.0055 (7)
C590.0237 (9)0.0181 (8)0.0173 (9)0.0072 (7)−0.0001 (7)−0.0002 (7)
C600.0185 (9)0.0175 (8)0.0204 (9)0.0045 (7)−0.0002 (7)0.0000 (7)
C610.0218 (9)0.0193 (8)0.0193 (9)0.0029 (7)−0.0030 (7)−0.0028 (7)
C620.0197 (9)0.0284 (10)0.0262 (10)0.0036 (8)−0.0006 (7)−0.0034 (8)
C630.0240 (11)0.0482 (13)0.0390 (13)0.0088 (9)0.0057 (9)−0.0063 (10)
C640.0259 (11)0.0259 (10)0.0538 (14)−0.0008 (8)0.0049 (9)0.0004 (9)
C650.0276 (11)0.0337 (11)0.0198 (10)−0.0015 (8)−0.0007 (8)−0.0072 (8)
C660.0340 (12)0.0375 (12)0.0263 (11)−0.0018 (9)0.0048 (9)0.0044 (9)

Geometric parameters (Å, °)

S1—O21.4257 (13)S2—O61.4292 (14)
S1—O31.4315 (13)S2—O51.4304 (14)
S1—O11.5674 (13)S2—O41.5671 (13)
S1—C51.7593 (18)S2—C381.7617 (19)
O1—C81.479 (2)O4—C411.483 (2)
C1—C21.504 (3)C34—C351.507 (3)
C1—H1A0.9800C34—H34A0.9800
C1—H1B0.9800C34—H34B0.9800
C1—H1C0.9800C34—H34C0.9800
C2—C31.392 (3)C35—C401.393 (3)
C2—C71.398 (3)C35—C361.394 (3)
C3—C41.389 (3)C36—C371.390 (3)
C3—H30.9500C36—H360.9500
C4—C51.386 (2)C37—C381.386 (3)
C4—H40.9500C37—H370.9500
C5—C61.390 (3)C38—C391.389 (3)
C6—C71.382 (3)C39—C401.394 (3)
C6—H60.9500C39—H390.9500
C7—H70.9500C40—H400.9500
C8—C91.510 (3)C41—C421.505 (3)
C8—C131.519 (3)C41—C461.518 (3)
C8—H81.0000C41—H411.0000
C9—C101.530 (3)C42—C431.530 (2)
C9—H9A0.9900C42—H42A0.9900
C9—H9B0.9900C42—H42B0.9900
C10—C111.549 (2)C43—C441.541 (2)
C10—H10A0.9900C43—H43A0.9900
C10—H10B0.9900C43—H43B0.9900
C11—C121.526 (2)C44—C451.528 (2)
C11—C11A1.544 (2)C44—C44A1.547 (2)
C11—C171.556 (2)C44—C501.555 (2)
C11A—H11A0.9800C44A—H44A0.9800
C11A—H11B0.9800C44A—H44B0.9800
C11A—H11C0.9800C44A—H44C0.9800
C12—C141.335 (2)C45—C471.331 (2)
C12—C131.519 (3)C45—C461.517 (3)
C13—H13A0.9900C46—H46A0.9900
C13—H13B0.9900C46—H46B0.9900
C14—C151.502 (2)C47—C481.503 (2)
C14—H140.9500C47—H470.9500
C15—C161.536 (2)C48—C491.534 (2)
C15—H15A0.9900C48—H48A0.9900
C15—H15B0.9900C48—H48B0.9900
C16—C211.523 (2)C49—C541.528 (2)
C16—C171.537 (2)C49—C501.539 (2)
C16—H161.0000C49—H491.0000
C17—C181.538 (2)C50—C511.536 (2)
C17—H171.0000C50—H501.0000
C18—C191.538 (2)C51—C521.542 (2)
C18—H18A0.9900C51—H51A0.9900
C18—H18B0.9900C51—H51B0.9900
C19—C201.532 (2)C52—C531.535 (2)
C19—H19A0.9900C52—H52A0.9900
C19—H19B0.9900C52—H52B0.9900
C20—C20A1.536 (2)C53—C53A1.542 (2)
C20—C211.547 (2)C53—C541.545 (2)
C20—C241.557 (2)C53—C571.552 (2)
C20A—H20A0.9800C53A—H53A0.9800
C20A—H20B0.9800C53A—H53B0.9800
C20A—H20C0.9800C53A—H53C0.9800
C21—C221.527 (2)C54—C551.533 (3)
C21—H211.0000C54—H541.0000
C22—C231.546 (3)C55—C561.550 (3)
C22—H22A0.9900C55—H55A0.9900
C22—H22B0.9900C55—H55B0.9900
C23—C241.556 (3)C56—C571.552 (3)
C23—H23A0.9900C56—H56A0.9900
C23—H23B0.9900C56—H56B0.9900
C24—C251.543 (3)C57—C581.542 (2)
C24—H241.0000C57—H571.0000
C25—C261.508 (3)C58—C591.508 (2)
C25—C25A1.539 (3)C58—C58A1.533 (3)
C25—H251.0000C58—H581.0000
C25A—H25A0.9800C58A—H58A0.9800
C25A—H25B0.9800C58A—H58B0.9800
C25A—H25C0.9800C58A—H58C0.9800
C26—C271.322 (3)C59—C601.324 (2)
C26—H260.9500C59—H590.9500
C27—C281.503 (2)C60—C611.506 (2)
C27—H270.9500C60—H600.9500
C28—C291.542 (3)C61—C651.536 (3)
C28—C321.544 (3)C61—C621.541 (3)
C28—H281.0000C61—H611.0000
C29—C301.531 (3)C62—C641.522 (3)
C29—C311.534 (3)C62—C631.523 (3)
C29—H291.0000C62—H621.0000
C30—H30A0.9800C63—H63A0.9800
C30—H30B0.9800C63—H63B0.9800
C30—H30C0.9800C63—H63C0.9800
C31—H31A0.9800C64—H64A0.9800
C31—H31B0.9800C64—H64B0.9800
C31—H31C0.9800C64—H64C0.9800
C32—C331.518 (3)C65—C661.518 (3)
C32—H32A0.9900C65—H65A0.9900
C32—H32B0.9900C65—H65B0.9900
C33—H33A0.9800C66—H66A0.9800
C33—H33B0.9800C66—H66B0.9800
C33—H33C0.9800C66—H66C0.9800
O2—S1—O3119.33 (8)O6—S2—O5119.26 (8)
O2—S1—O1104.43 (7)O6—S2—O4104.35 (7)
O3—S1—O1110.39 (8)O5—S2—O4109.84 (8)
O2—S1—C5109.95 (8)O6—S2—C38109.82 (9)
O3—S1—C5108.60 (8)O5—S2—C38108.38 (8)
O1—S1—C5102.86 (8)O4—S2—C38104.11 (8)
C8—O1—S1117.46 (11)C41—O4—S2118.40 (11)
C2—C1—H1A109.5C35—C34—H34A109.5
C2—C1—H1B109.5C35—C34—H34B109.5
H1A—C1—H1B109.5H34A—C34—H34B109.5
C2—C1—H1C109.5C35—C34—H34C109.5
H1A—C1—H1C109.5H34A—C34—H34C109.5
H1B—C1—H1C109.5H34B—C34—H34C109.5
C3—C2—C7118.71 (17)C40—C35—C36118.45 (18)
C3—C2—C1120.74 (18)C40—C35—C34120.45 (18)
C7—C2—C1120.55 (18)C36—C35—C34121.08 (18)
C4—C3—C2120.85 (17)C37—C36—C35121.01 (17)
C4—C3—H3119.6C37—C36—H36119.5
C2—C3—H3119.6C35—C36—H36119.5
C5—C4—C3119.17 (17)C38—C37—C36119.37 (17)
C5—C4—H4120.4C38—C37—H37120.3
C3—C4—H4120.4C36—C37—H37120.3
C4—C5—C6121.14 (17)C37—C38—C39121.01 (17)
C4—C5—S1120.04 (14)C37—C38—S2119.81 (14)
C6—C5—S1118.82 (14)C39—C38—S2119.16 (14)
C7—C6—C5118.96 (18)C38—C39—C40118.78 (17)
C7—C6—H6120.5C38—C39—H39120.6
C5—C6—H6120.5C40—C39—H39120.6
C6—C7—C2121.17 (18)C35—C40—C39121.38 (18)
C6—C7—H7119.4C35—C40—H40119.3
C2—C7—H7119.4C39—C40—H40119.3
O1—C8—C9107.66 (14)O4—C41—C42108.23 (14)
O1—C8—C13107.31 (15)O4—C41—C46107.85 (14)
C9—C8—C13112.22 (15)C42—C41—C46111.52 (15)
O1—C8—H8109.9O4—C41—H41109.7
C9—C8—H8109.9C42—C41—H41109.7
C13—C8—H8109.9C46—C41—H41109.7
C8—C9—C10110.04 (15)C41—C42—C43109.48 (15)
C8—C9—H9A109.7C41—C42—H42A109.8
C10—C9—H9A109.7C43—C42—H42A109.8
C8—C9—H9B109.7C41—C42—H42B109.8
C10—C9—H9B109.7C43—C42—H42B109.8
H9A—C9—H9B108.2H42A—C42—H42B108.2
C9—C10—C11114.88 (16)C42—C43—C44114.46 (15)
C9—C10—H10A108.5C42—C43—H43A108.6
C11—C10—H10A108.5C44—C43—H43A108.6
C9—C10—H10B108.5C42—C43—H43B108.6
C11—C10—H10B108.5C44—C43—H43B108.6
H10A—C10—H10B107.5H43A—C43—H43B107.6
C12—C11—C11A107.17 (15)C45—C44—C43109.69 (14)
C12—C11—C10110.18 (14)C45—C44—C44A107.78 (14)
C11A—C11—C10109.72 (15)C43—C44—C44A109.68 (15)
C12—C11—C17108.98 (14)C45—C44—C50108.97 (14)
C11A—C11—C17112.24 (14)C43—C44—C50108.65 (14)
C10—C11—C17108.54 (14)C44A—C44—C50112.04 (14)
C11—C11A—H11A109.5C44—C44A—H44A109.5
C11—C11A—H11B109.5C44—C44A—H44B109.5
H11A—C11A—H11B109.5H44A—C44A—H44B109.5
C11—C11A—H11C109.5C44—C44A—H44C109.5
H11A—C11A—H11C109.5H44A—C44A—H44C109.5
H11B—C11A—H11C109.5H44B—C44A—H44C109.5
C14—C12—C13120.64 (16)C47—C45—C46120.50 (16)
C14—C12—C11122.48 (16)C47—C45—C44122.27 (16)
C13—C12—C11116.71 (15)C46—C45—C44117.15 (15)
C8—C13—C12110.98 (15)C45—C46—C41111.39 (15)
C8—C13—H13A109.4C45—C46—H46A109.3
C12—C13—H13A109.4C41—C46—H46A109.3
C8—C13—H13B109.4C45—C46—H46B109.3
C12—C13—H13B109.4C41—C46—H46B109.3
H13A—C13—H13B108.0H46A—C46—H46B108.0
C12—C14—C15124.96 (16)C45—C47—C48125.15 (16)
C12—C14—H14117.5C45—C47—H47117.4
C15—C14—H14117.5C48—C47—H47117.4
C14—C15—C16113.52 (14)C47—C48—C49113.49 (14)
C14—C15—H15A108.9C47—C48—H48A108.9
C16—C15—H15A108.9C49—C48—H48A108.9
C14—C15—H15B108.9C47—C48—H48B108.9
C16—C15—H15B108.9C49—C48—H48B108.9
H15A—C15—H15B107.7H48A—C48—H48B107.7
C21—C16—C15111.21 (14)C54—C49—C48111.06 (14)
C21—C16—C17110.09 (14)C54—C49—C50110.31 (14)
C15—C16—C17109.65 (14)C48—C49—C50109.12 (14)
C21—C16—H16108.6C54—C49—H49108.8
C15—C16—H16108.6C48—C49—H49108.8
C17—C16—H16108.6C50—C49—H49108.8
C16—C17—C18113.36 (14)C51—C50—C49112.82 (14)
C16—C17—C11111.53 (14)C51—C50—C44112.92 (14)
C18—C17—C11113.09 (14)C49—C50—C44111.62 (14)
C16—C17—H17106.1C51—C50—H50106.3
C18—C17—H17106.1C49—C50—H50106.3
C11—C17—H17106.1C44—C50—H50106.3
C17—C18—C19114.33 (15)C50—C51—C52114.02 (14)
C17—C18—H18A108.7C50—C51—H51A108.7
C19—C18—H18A108.7C52—C51—H51A108.7
C17—C18—H18B108.7C50—C51—H51B108.7
C19—C18—H18B108.7C52—C51—H51B108.7
H18A—C18—H18B107.6H51A—C51—H51B107.6
C20—C19—C18111.48 (15)C53—C52—C51110.86 (14)
C20—C19—H19A109.3C53—C52—H52A109.5
C18—C19—H19A109.3C51—C52—H52A109.5
C20—C19—H19B109.3C53—C52—H52B109.5
C18—C19—H19B109.3C51—C52—H52B109.5
H19A—C19—H19B108.0H52A—C52—H52B108.1
C19—C20—C20A110.43 (15)C52—C53—C53A110.86 (14)
C19—C20—C21106.59 (14)C52—C53—C54106.80 (14)
C20A—C20—C21112.48 (15)C53A—C53—C54112.19 (14)
C19—C20—C24116.53 (14)C52—C53—C57116.91 (14)
C20A—C20—C24110.01 (14)C53A—C53—C57109.47 (14)
C21—C20—C24100.44 (13)C54—C53—C57100.16 (13)
C20—C20A—H20A109.5C53—C53A—H53A109.5
C20—C20A—H20B109.5C53—C53A—H53B109.5
H20A—C20A—H20B109.5H53A—C53A—H53B109.5
C20—C20A—H20C109.5C53—C53A—H53C109.5
H20A—C20A—H20C109.5H53A—C53A—H53C109.5
H20B—C20A—H20C109.5H53B—C53A—H53C109.5
C16—C21—C22118.58 (15)C49—C54—C55118.65 (15)
C16—C21—C20114.46 (14)C49—C54—C53114.87 (14)
C22—C21—C20104.56 (14)C55—C54—C53104.15 (14)
C16—C21—H21106.1C49—C54—H54106.1
C22—C21—H21106.1C55—C54—H54106.1
C20—C21—H21106.1C53—C54—H54106.1
C21—C22—C23104.07 (14)C54—C55—C56104.04 (15)
C21—C22—H22A110.9C54—C55—H55A110.9
C23—C22—H22A110.9C56—C55—H55A110.9
C21—C22—H22B110.9C54—C55—H55B110.9
C23—C22—H22B110.9C56—C55—H55B110.9
H22A—C22—H22B109.0H55A—C55—H55B109.0
C22—C23—C24107.21 (14)C55—C56—C57106.77 (14)
C22—C23—H23A110.3C55—C56—H56A110.4
C24—C23—H23A110.3C57—C56—H56A110.4
C22—C23—H23B110.3C55—C56—H56B110.4
C24—C23—H23B110.3C57—C56—H56B110.4
H23A—C23—H23B108.5H56A—C56—H56B108.6
C25—C24—C23111.24 (14)C58—C57—C56112.65 (15)
C25—C24—C20118.58 (15)C58—C57—C53118.51 (14)
C23—C24—C20103.41 (14)C56—C57—C53103.44 (14)
C25—C24—H24107.7C58—C57—H57107.2
C23—C24—H24107.7C56—C57—H57107.2
C20—C24—H24107.7C53—C57—H57107.2
C26—C25—C25A109.16 (16)C59—C58—C58A108.23 (15)
C26—C25—C24110.43 (15)C59—C58—C57111.30 (14)
C25A—C25—C24113.53 (15)C58A—C58—C57112.29 (14)
C26—C25—H25107.8C59—C58—H58108.3
C25A—C25—H25107.8C58A—C58—H58108.3
C24—C25—H25107.8C57—C58—H58108.3
C25—C25A—H25A109.5C58—C58A—H58A109.5
C25—C25A—H25B109.5C58—C58A—H58B109.5
H25A—C25A—H25B109.5H58A—C58A—H58B109.5
C25—C25A—H25C109.5C58—C58A—H58C109.5
H25A—C25A—H25C109.5H58A—C58A—H58C109.5
H25B—C25A—H25C109.5H58B—C58A—H58C109.5
C27—C26—C25124.38 (17)C60—C59—C58125.96 (16)
C27—C26—H26117.8C60—C59—H59117.0
C25—C26—H26117.8C58—C59—H59117.0
C26—C27—C28126.95 (17)C59—C60—C61125.34 (16)
C26—C27—H27116.5C59—C60—H60117.3
C28—C27—H27116.5C61—C60—H60117.3
C27—C28—C29111.71 (15)C60—C61—C65109.78 (15)
C27—C28—C32108.93 (15)C60—C61—C62113.62 (16)
C29—C28—C32111.10 (15)C65—C61—C62111.72 (15)
C27—C28—H28108.3C60—C61—H61107.1
C29—C28—H28108.3C65—C61—H61107.1
C32—C28—H28108.3C62—C61—H61107.1
C30—C29—C31109.07 (16)C64—C62—C63110.29 (18)
C30—C29—C28112.32 (15)C64—C62—C61113.65 (16)
C31—C29—C28112.07 (16)C63—C62—C61111.00 (16)
C30—C29—H29107.7C64—C62—H62107.2
C31—C29—H29107.7C63—C62—H62107.2
C28—C29—H29107.7C61—C62—H62107.2
C29—C30—H30A109.5C62—C63—H63A109.5
C29—C30—H30B109.5C62—C63—H63B109.5
H30A—C30—H30B109.5H63A—C63—H63B109.5
C29—C30—H30C109.5C62—C63—H63C109.5
H30A—C30—H30C109.5H63A—C63—H63C109.5
H30B—C30—H30C109.5H63B—C63—H63C109.5
C29—C31—H31A109.5C62—C64—H64A109.5
C29—C31—H31B109.5C62—C64—H64B109.5
H31A—C31—H31B109.5H64A—C64—H64B109.5
C29—C31—H31C109.5C62—C64—H64C109.5
H31A—C31—H31C109.5H64A—C64—H64C109.5
H31B—C31—H31C109.5H64B—C64—H64C109.5
C33—C32—C28114.20 (17)C66—C65—C61113.44 (16)
C33—C32—H32A108.7C66—C65—H65A108.9
C28—C32—H32A108.7C61—C65—H65A108.9
C33—C32—H32B108.7C66—C65—H65B108.9
C28—C32—H32B108.7C61—C65—H65B108.9
H32A—C32—H32B107.6H65A—C65—H65B107.7
C32—C33—H33A109.5C65—C66—H66A109.5
C32—C33—H33B109.5C65—C66—H66B109.5
H33A—C33—H33B109.5H66A—C66—H66B109.5
C32—C33—H33C109.5C65—C66—H66C109.5
H33A—C33—H33C109.5H66A—C66—H66C109.5
H33B—C33—H33C109.5H66B—C66—H66C109.5
O2—S1—O1—C8−177.24 (12)O6—S2—O4—C41−178.70 (12)
O3—S1—O1—C8−47.79 (14)O5—S2—O4—C4152.34 (14)
C5—S1—O1—C867.92 (13)C38—S2—O4—C41−63.53 (14)
C7—C2—C3—C40.4 (3)C40—C35—C36—C37−0.8 (3)
C1—C2—C3—C4−178.74 (18)C34—C35—C36—C37177.58 (17)
C2—C3—C4—C5−0.1 (3)C35—C36—C37—C380.2 (3)
C3—C4—C5—C6−0.4 (3)C36—C37—C38—C390.6 (3)
C3—C4—C5—S1179.51 (14)C36—C37—C38—S2179.16 (14)
O2—S1—C5—C4129.06 (15)O6—S2—C38—C37−132.77 (15)
O3—S1—C5—C4−3.17 (17)O5—S2—C38—C37−0.91 (17)
O1—S1—C5—C4−120.16 (15)O4—S2—C38—C37115.98 (15)
O2—S1—C5—C6−51.05 (17)O6—S2—C38—C3945.84 (16)
O3—S1—C5—C6176.72 (14)O5—S2—C38—C39177.70 (14)
O1—S1—C5—C659.72 (16)O4—S2—C38—C39−65.41 (16)
C4—C5—C6—C70.4 (3)C37—C38—C39—C40−0.7 (3)
S1—C5—C6—C7−179.44 (15)S2—C38—C39—C40−179.27 (14)
C5—C6—C7—C2−0.1 (3)C36—C35—C40—C390.7 (3)
C3—C2—C7—C6−0.4 (3)C34—C35—C40—C39−177.70 (17)
C1—C2—C7—C6178.82 (19)C38—C39—C40—C350.1 (3)
S1—O1—C8—C9113.97 (14)S2—O4—C41—C42116.19 (14)
S1—O1—C8—C13−125.04 (13)S2—O4—C41—C46−123.02 (13)
O1—C8—C9—C10175.44 (15)O4—C41—C42—C43177.69 (14)
C13—C8—C9—C1057.6 (2)C46—C41—C42—C4359.2 (2)
C8—C9—C10—C11−54.0 (2)C41—C42—C43—C44−57.0 (2)
C9—C10—C11—C1246.7 (2)C42—C43—C44—C4548.1 (2)
C9—C10—C11—C11A−71.1 (2)C42—C43—C44—C44A−70.12 (19)
C9—C10—C11—C17165.97 (15)C42—C43—C44—C50167.10 (14)
C11A—C11—C12—C14−100.7 (2)C43—C44—C45—C47139.53 (17)
C10—C11—C12—C14140.00 (18)C44A—C44—C45—C47−101.10 (19)
C17—C11—C12—C1421.0 (2)C50—C44—C45—C4720.7 (2)
C11A—C11—C12—C1374.55 (19)C43—C44—C45—C46−43.9 (2)
C10—C11—C12—C13−44.8 (2)C44A—C44—C45—C4675.46 (19)
C17—C11—C12—C13−163.77 (15)C50—C44—C45—C46−162.74 (14)
O1—C8—C13—C12−173.35 (14)C47—C45—C46—C41−135.25 (18)
C9—C8—C13—C12−55.3 (2)C44—C45—C46—C4148.1 (2)
C14—C12—C13—C8−134.95 (18)O4—C41—C46—C45−173.52 (14)
C11—C12—C13—C849.7 (2)C42—C41—C46—C45−54.8 (2)
C13—C12—C14—C15−174.45 (16)C46—C45—C47—C48−176.09 (17)
C11—C12—C14—C150.6 (3)C44—C45—C47—C480.4 (3)
C12—C14—C15—C168.2 (3)C45—C47—C48—C499.2 (3)
C14—C15—C16—C21−160.27 (14)C47—C48—C49—C54−161.03 (15)
C14—C15—C16—C17−38.3 (2)C47—C48—C49—C50−39.2 (2)
C21—C16—C17—C18−46.6 (2)C54—C49—C50—C51−47.0 (2)
C15—C16—C17—C18−169.27 (14)C48—C49—C50—C51−169.30 (15)
C21—C16—C17—C11−175.61 (13)C54—C49—C50—C44−175.44 (14)
C15—C16—C17—C1161.72 (18)C48—C49—C50—C4462.29 (18)
C12—C11—C17—C16−51.84 (18)C45—C44—C50—C51179.78 (14)
C11A—C11—C17—C1666.72 (18)C43—C44—C50—C5160.30 (18)
C10—C11—C17—C16−171.84 (14)C44A—C44—C50—C51−61.04 (19)
C12—C11—C17—C18179.01 (15)C45—C44—C50—C49−51.86 (18)
C11A—C11—C17—C18−62.44 (19)C43—C44—C50—C49−171.34 (14)
C10—C11—C17—C1859.00 (18)C44A—C44—C50—C4967.32 (18)
C16—C17—C18—C1946.6 (2)C49—C50—C51—C5248.9 (2)
C11—C17—C18—C19174.85 (15)C44—C50—C51—C52176.59 (14)
C17—C18—C19—C20−52.9 (2)C50—C51—C52—C53−55.0 (2)
C18—C19—C20—C20A−65.06 (19)C51—C52—C53—C53A−64.76 (18)
C18—C19—C20—C2157.39 (18)C51—C52—C53—C5457.74 (18)
C18—C19—C20—C24168.49 (15)C51—C52—C53—C57168.83 (14)
C15—C16—C21—C22−57.8 (2)C48—C49—C54—C55−59.8 (2)
C17—C16—C21—C22−179.55 (15)C50—C49—C54—C55179.12 (15)
C15—C16—C21—C20177.98 (14)C48—C49—C54—C53176.18 (15)
C17—C16—C21—C2056.24 (18)C50—C49—C54—C5355.06 (19)
C19—C20—C21—C16−61.51 (18)C52—C53—C54—C49−60.29 (18)
C20A—C20—C21—C1659.65 (19)C53A—C53—C54—C4961.37 (19)
C24—C20—C21—C16176.56 (14)C57—C53—C54—C49177.40 (14)
C19—C20—C21—C22167.10 (14)C52—C53—C54—C55168.28 (14)
C20A—C20—C21—C22−71.74 (18)C53A—C53—C54—C55−70.06 (18)
C24—C20—C21—C2245.18 (16)C57—C53—C54—C5545.97 (17)
C16—C21—C22—C23−161.85 (15)C49—C54—C55—C56−161.69 (15)
C20—C21—C22—C23−32.90 (18)C53—C54—C55—C56−32.50 (18)
C21—C22—C23—C247.61 (19)C54—C55—C56—C576.2 (2)
C22—C23—C24—C25148.40 (15)C55—C56—C57—C58151.20 (15)
C22—C23—C24—C2020.06 (18)C55—C56—C57—C5322.03 (18)
C19—C20—C24—C2582.57 (19)C52—C53—C57—C5878.6 (2)
C20A—C20—C24—C25−44.1 (2)C53A—C53—C57—C58−48.5 (2)
C21—C20—C24—C25−162.83 (15)C54—C53—C57—C58−166.58 (15)
C19—C20—C24—C23−153.79 (15)C52—C53—C57—C56−155.95 (15)
C20A—C20—C24—C2379.55 (17)C53A—C53—C57—C5676.96 (17)
C21—C20—C24—C23−39.18 (16)C54—C53—C57—C56−41.10 (16)
C23—C24—C25—C2653.5 (2)C56—C57—C58—C5956.8 (2)
C20—C24—C25—C26173.16 (15)C53—C57—C58—C59177.69 (15)
C23—C24—C25—C25A176.46 (17)C56—C57—C58—C58A178.32 (15)
C20—C24—C25—C25A−63.9 (2)C53—C57—C58—C58A−60.8 (2)
C25A—C25—C26—C27117.9 (2)C58A—C58—C59—C60112.9 (2)
C24—C25—C26—C27−116.6 (2)C57—C58—C59—C60−123.2 (2)
C25—C26—C27—C28−177.30 (17)C58—C59—C60—C61−173.26 (17)
C26—C27—C28—C29−123.9 (2)C59—C60—C61—C65115.6 (2)
C26—C27—C28—C32113.0 (2)C59—C60—C61—C62−118.5 (2)
C27—C28—C29—C3045.2 (2)C60—C61—C62—C64−66.8 (2)
C32—C28—C29—C30167.11 (16)C65—C61—C62—C6458.0 (2)
C27—C28—C29—C31168.45 (16)C60—C61—C62—C6358.2 (2)
C32—C28—C29—C31−69.7 (2)C65—C61—C62—C63−176.96 (17)
C27—C28—C32—C33−63.3 (2)C60—C61—C65—C66−71.4 (2)
C29—C28—C32—C33173.28 (18)C62—C61—C65—C66161.63 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O3i0.952.493.217 (2)134
C13—H13b···O60.992.543.519 (2)172
C40—H40···O5ii0.952.483.193 (2)131
C42—H42a···O20.992.563.548 (2)175
C44a—H44c···O20.982.543.390 (2)145

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5438).

References

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