Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1336
https://doi.org/10.1107/S1600536810016661

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

Kamal Aziz Ketuly,a‡ A. Hamid A. Hadi,a Hamid Khaledia and Edward R. T. Tiekinka*

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 5 May 2010; accepted 6 May 2010; online 15 May 2010)

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[Partridge, J. J., Faber, S. & Uskokovic, M. R. (1974). Helv. Chim. Acta, 57, 764-771.]); Khripach et al. (2002[Khripach, V. A., Zhabinskii, V. N., Konstantinova, O. V., Khripach, N. B., Antonchick, A. P. & Schneider, B. (2002). Steroids, 67, 597-603.]); Foley et al. (2010[Foley, D. A., O'Callaghan, Y., O'Brien, N. M., McCarthy, F. O. & MaGuire, A. R. (2010). J. Agric. Food Chem. 58, 1165-1173.]); Ketuly et al. (1997[Ketuly, K. A., Yufit, D. S., Brooks, C. J. W. & Freer, A. A. (1997). Acta Cryst. C53, 981-982.]). For the synthesis, see: Foley et al. (2010[Foley, D. A., O'Callaghan, Y., O'Brien, N. M., McCarthy, F. O. & MaGuire, A. R. (2010). J. Agric. Food Chem. 58, 1165-1173.]).

[Scheme 1]

Experimental

Crystal data

  • C36H54O3S

  • Mr = 566.86

  • Triclinic, P 1

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.669, Tmax = 0.746

  • 15647 measured reflections

  • 13115 independent reflections

  • 12382 reflections with I > 2σ(I)

  • Rint = 0.018
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 5643 Friedel pairs

  • Flack parameter: 0.02 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7—H7⋯O3i 0.95 2.49 3.217 (2) 134
C13—H13B⋯O6 0.99 2.54 3.519 (2) 172
C40—H40⋯O5ii 0.95 2.48 3.193 (2) 131
C42—H42A⋯O2 0.99 2.56 3.548 (2) 175
C44A—H44C⋯O2 0.98 2.54 3.390 (2) 145
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and Qmol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graphics Model. 19, 557-559.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016661/hb5438Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Structure description top

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.

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the first independent molecule in (I) displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of the second independent molecule in (I) showing displacement ellipsoids at the 50% probability level.
[Figure 3] Fig. 3. Overlap diagram highlighting the different conformations of the first (red) and second (blue) independent molecules in (I).
[Figure 4] 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.
[Figure 5] 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; and H, green.
(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 top
Crystal data top
C36H54O3SZ = 2
Mr = 566.86F(000) = 620
Triclinic, P1Dx = 1.155 Mg m−3
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 mm−1
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 top
Bruker SMART APEX CCD
diffractometer		13115 independent reflections
Radiation source: fine-focus sealed tube12382 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
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) = 0.089 w = 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 Å−3
735 parametersΔρmin = −0.37 e Å−3
3 restraintsAbsolute structure: Flack (1983), 5643 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (4)
Crystal data top
C36H54O3Sγ = 101.153 (1)°
Mr = 566.86V = 1630.23 (3) Å3
Triclinic, P1Z = 2
a = 7.0361 (1) ÅMo Kα radiation
b = 11.2350 (1) ŵ = 0.13 mm−1
c = 21.1550 (2) ÅT = 100 K
α = 90.777 (1)°0.49 × 0.37 × 0.27 mm
β = 96.166 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		13115 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		12382 reflections with I > 2σ(I)
Tmin = 0.669, Tmax = 0.746Rint = 0.018
15647 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.089Δρmax = 0.35 e Å−3
S = 1.02Δρmin = −0.37 e Å−3
13115 reflectionsAbsolute structure: Flack (1983), 5643 Friedel pairs
735 parametersAbsolute structure parameter: 0.02 (4)
3 restraints
Special details top

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) top
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC36H54O3S
Mr566.86
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.0361 (1), 11.2350 (1), 21.1550 (2)
α, β, γ (°)90.777 (1), 96.166 (1), 101.153 (1)
V (Å3)1630.23 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.13
Crystal size (mm)0.49 × 0.37 × 0.27
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.669, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		15647, 13115, 12382
Rint0.018
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.089, 1.02
No. of reflections13115
No. of parameters735
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.35, −0.37
Absolute structureFlack (1983), 5643 Friedel pairs
Absolute structure parameter0.02 (4)

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
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

‡Additional correspondence author, e-mail: kketuly@um.edu.my.

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFoley, D. A., O'Callaghan, Y., O'Brien, N. M., McCarthy, F. O. & MaGuire, A. R. (2010). J. Agric. Food Chem. 58, 1165–1173.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationGans, J. & Shalloway, D. (2001). J. Mol. Graphics Model. 19, 557–559.  Web of Science CrossRef CAS Google Scholar
 First citationKetuly, K. A., Yufit, D. S., Brooks, C. J. W. & Freer, A. A. (1997). Acta Cryst. C53, 981–982.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationKhripach, V. A., Zhabinskii, V. N., Konstantinova, O. V., Khripach, N. B., Antonchick, A. P. & Schneider, B. (2002). Steroids, 67, 597–603.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationPartridge, J. J., Faber, S. & Uskokovic, M. R. (1974). Helv. Chim. Acta, 57, 764–771.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1336
https://doi.org/10.1107/S1600536810016661
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS