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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1227.
Published online 2009 May 7. doi:  10.1107/S1600536809015694
PMCID: PMC2969703

4,5,6-Tri-O-acetyl-2,3-di-S-ethyl-2,3-dithio-d-allose diethyl dithio­acetal

Abstract

The title compound, C20H36O6S4, was obtained by ethanethiol­ysis of 3,5,6-tri-O-acetyl-1,2-O-isopropyl­idene-α-d-gluco­furan­­ose. One of the ethyl groups is disordered over two sites with refined occupancies of 0.869 (6) and 0.131 (6). Compared with the precursor, the absolute configuration of the stereocenters at positions C-3 and C-2 are inverted and maintained, respectively.

Related literature

For the bioactiviy of nucleosides, see: Zhang et al. (2007 [triangle]); Merino et al. (2008 [triangle]). For the structure of the precursor, 3,5,6-tri-O-acetyl-1,2-O-isopropyl­idene-α-d-glucofuran­ose, see: Wu et al. (2009 [triangle]). For related structures, see: Bethel & Ferrier (1972 [triangle]); Berrang & Hortor (1970 [triangle]); Divjaković et al. (1992 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1227-scheme1.jpg

Experimental

Crystal data

  • C20H36O6S4
  • M r = 500.73
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1227-efi1.jpg
  • a = 8.3395 (12) Å
  • b = 16.726 (2) Å
  • c = 9.2027 (14) Å
  • β = 95.772 (5)°
  • V = 1277.2 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 113 K
  • 0.26 × 0.20 × 0.18 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.902, T max = 0.931
  • 16052 measured reflections
  • 6060 independent reflections
  • 5802 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.066
  • S = 1.04
  • 6060 reflections
  • 298 parameters
  • 23 restraints
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.29 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2919 Friedel pairs
  • Flack parameter: −0.03 (4)

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015694/lh2804sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015694/lh2804Isup2.hkl

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

Acknowledgments

The authors thank the National Science Foundation of China (30340070) and the Ministry of Science and Technology of China (2006 A A100216) for financial support.

supplementary crystallographic information

Comment

Nucleosides are important compounds due to their extensive bioactivity in antitumor and antivirus (Zhang et al., 2007, Merino et al., 2008). In the course of our studies in the synthesis of nucleoside analogues, an ethanethio substituted thioacetal product was obtained as ethanethiolysis of 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (Wu et al., 2009). The purpose of the structure determination was to establish the position of the substituents of the ethanethio groups and the molecular conformation of the title compound. In contrast to its precursor, the absolute configuration of C-3 and C-2 are inverted and maintained, respectively, which is similar to the documented results (Berrang & Hortor, 1970; Bethel & Ferrier, 1972), but disagrees with the molecular structure reported by Divjaković (Divjakovic et al., 1992). Both the molecular conformation and structure are consistent with our desired intermediates for the synthesis of the corresponding 2',3'-dideoxy-2',3'-dimercaptoribonucleosides.

Experimental

ZnBr2 (0.54 g, 2.4 mmol) was added to a solution of 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (0.67 g, 2.0 mmol) and ethanethiol (0.78 ml, 10 mmol) in dry CH2Cl2 (10 ml). After 5 h, saturated aqueous solution of NaHCO3 (20 ml) was added and separated. The organic layer was washed with brine, dried with MgSO4 and concentrated under reduced pressure. The residue was isolated through short column chromatography on silica gel, which was eluded with EtOAc-petroleum to give the target compound (0.78 g, 78%). M. p. 62°, 1H-NMR(CDCl3, p.p.m.): 1.28 (m, 12 H), 2.06 (m, 9 H), 2.75 (m, 8 H), 3.07 (dd, 1 H), 3.48 (dd, 1 H), 4.20 (m, 1 H), 4.49 (dd, 1 H), 4.6 4 (d, 1 H), 5.54 (m, 1 H), 5.89 (dd, 1 H); 13C-NMR(CDCl3, p.p.m.):14.60, 14.74, 14.85, 14.92, 15.02, 21.23, 21.27, 25.79, 26.39, 28.31, 30.24, 51.47, 57.30, 57.48, 62.56, 71.96, 72.78, 169.19, 169.61, 170.82; HRMS (EI) m/z calculated for C20H36O6S4 500.13, found 500.14.

50 mg of the obtained product was dissolved in petroleum ether (5 ml) and the solution was kept at room temperature for 2 days to give colorless single crystals.

Refinement

C—H were included in the riding model approximation with C—H distances 0.98–1.00 Å, and with Uiso=1.2Ueq(C) or 1.5Ueq(Cmethyl).

One of the ethyl groups is disordered over two sites with refined occupancies of 0.869 (6) and 0.131 (6). The restained distance of C13—C14 refined to 1.513 (4)Å and C13'-C14' refined to 1.502 (19) Å.

Figures

Fig. 1.
Molecular structure of the title compound with thermal displacement ellipsoids drawn at the 30% probability level. Open bonds show the disorder component.

Crystal data

C20H36O6S4F(000) = 536
Mr = 500.73Dx = 1.302 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ybCell parameters from 4760 reflections
a = 8.3395 (12) Åθ = 2.2–27.9°
b = 16.726 (2) ŵ = 0.40 mm1
c = 9.2027 (14) ÅT = 113 K
β = 95.772 (5)°Block, colorless
V = 1277.2 (3) Å30.26 × 0.20 × 0.18 mm
Z = 2

Data collection

Rigaku Saturn diffractometer6060 independent reflections
Radiation source: rotating anode5802 reflections with I > 2σ(I)
confocalRint = 0.032
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 2.2°
ω scansh = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −21→22
Tmin = 0.902, Tmax = 0.931l = −12→12
16052 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.066w = 1/[σ2(Fo2) + (0.0326P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6060 reflectionsΔρmax = 0.20 e Å3
298 parametersΔρmin = −0.29 e Å3
23 restraintsAbsolute structure: Flack (1983), 2919 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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*/UeqOcc. (<1)
S10.74081 (5)−0.08494 (3)0.79166 (5)0.02103 (10)
S20.70511 (5)0.08746 (3)0.88989 (5)0.02203 (10)
S30.41930 (5)0.00547 (3)0.66199 (5)0.01940 (10)
S40.85901 (5)0.02564 (3)0.42590 (5)0.02148 (10)
O10.56270 (15)−0.06561 (7)0.23706 (13)0.0182 (3)
O20.32000 (18)−0.12020 (10)0.25917 (18)0.0405 (4)
O30.54225 (14)0.14186 (7)0.33931 (12)0.0169 (3)
O40.68402 (15)0.21225 (8)0.18563 (14)0.0269 (3)
O50.25647 (13)0.10093 (8)0.19236 (13)0.0209 (3)
O60.26208 (18)0.22570 (8)0.10243 (18)0.0378 (4)
C10.74322 (19)0.02080 (11)0.74033 (17)0.0171 (3)
H10.85210.03360.70990.021*
C20.61765 (18)0.03465 (11)0.60845 (18)0.0156 (3)
H20.61430.09330.58730.019*
C30.66042 (18)−0.00888 (10)0.46908 (17)0.0147 (3)
H30.6708−0.06700.49330.018*
C40.53286 (19)−0.00125 (11)0.33657 (17)0.0148 (3)
H40.4224−0.00680.36890.018*
C50.5413 (2)0.07353 (10)0.24304 (18)0.0164 (4)
H50.64400.07270.19570.020*
C60.3999 (2)0.08169 (12)0.12490 (18)0.0202 (4)
H6A0.42270.12440.05540.024*
H6B0.38430.03090.07000.024*
C70.8968 (2)−0.08772 (14)0.94224 (19)0.0284 (4)
H7A0.8763−0.04441.01120.034*
H7B0.8888−0.13910.99440.034*
C81.0684 (2)−0.07889 (15)0.9010 (3)0.0398 (5)
H8A1.0926−0.12300.83660.060*
H8B1.1441−0.08010.98960.060*
H8C1.0788−0.02790.85030.060*
C90.8906 (2)0.14400 (14)0.9124 (2)0.0311 (5)
H9A0.89240.17591.00310.037*
H9B0.98210.10610.92470.037*
C100.9154 (3)0.19954 (14)0.7876 (3)0.0395 (5)
H10A0.92220.16830.69840.059*
H10B1.01550.22970.81040.059*
H10C0.82450.23680.77290.059*
C110.2932 (2)0.08823 (13)0.59307 (19)0.0237 (4)
H11A0.31060.09750.48960.028*
H11B0.17890.07300.59620.028*
C120.3242 (2)0.16570 (13)0.6765 (2)0.0302 (5)
H12A0.29850.15850.77730.045*
H12B0.25610.20800.62960.045*
H12C0.43780.18060.67660.045*
C130.9482 (3)−0.06248 (16)0.3541 (3)0.0317 (8)0.869 (6)
H13A0.8677−0.08830.28260.038*0.869 (6)
H13B1.0406−0.04610.30130.038*0.869 (6)
C141.0059 (4)−0.1230 (2)0.4699 (3)0.0428 (9)0.869 (6)
H14A1.0905−0.09910.53780.064*0.869 (6)
H14B1.0490−0.17000.42330.064*0.869 (6)
H14C0.9154−0.13920.52350.064*0.869 (6)
C13'0.9867 (15)−0.0625 (8)0.4615 (17)0.024 (5)0.131 (6)
H13C1.0967−0.04880.43790.029*0.131 (6)
H13D0.9937−0.07410.56740.029*0.131 (6)
C14'0.935 (2)−0.1377 (8)0.381 (2)0.036 (4)0.131 (6)
H14D0.8573−0.16650.43390.054*0.131 (6)
H14E1.0297−0.17170.37220.054*0.131 (6)
H14F0.8855−0.12400.28270.054*0.131 (6)
C150.4443 (2)−0.12014 (11)0.20382 (19)0.0200 (4)
C160.4899 (3)−0.17588 (12)0.0885 (2)0.0277 (4)
H16A0.4155−0.22140.08050.042*
H16B0.6000−0.19520.11430.042*
H16C0.4843−0.1477−0.00530.042*
C170.6157 (2)0.20907 (11)0.2941 (2)0.0209 (4)
C180.5959 (3)0.27634 (12)0.3979 (2)0.0326 (5)
H18A0.64850.32440.36440.049*
H18B0.64540.26170.49540.049*
H18C0.48100.28710.40210.049*
C190.2065 (2)0.17773 (11)0.1783 (2)0.0221 (4)
C200.0766 (2)0.19526 (13)0.2743 (2)0.0301 (5)
H20A0.12460.20330.37480.045*
H20B0.00120.15020.27120.045*
H20C0.01870.24370.23970.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0232 (2)0.0209 (2)0.0183 (2)−0.00083 (19)−0.00179 (18)0.00364 (18)
S20.0236 (2)0.0275 (2)0.0155 (2)−0.00207 (19)0.00384 (17)−0.00323 (19)
S30.0155 (2)0.0251 (2)0.0183 (2)−0.00173 (18)0.00489 (16)0.00091 (18)
S40.01363 (19)0.0294 (3)0.0218 (2)−0.00129 (18)0.00362 (16)0.00257 (19)
O10.0183 (6)0.0201 (7)0.0166 (6)−0.0007 (5)0.0034 (5)−0.0072 (5)
O20.0312 (8)0.0411 (9)0.0523 (10)−0.0176 (7)0.0194 (7)−0.0234 (8)
O30.0213 (6)0.0138 (6)0.0157 (6)−0.0013 (5)0.0026 (5)0.0002 (5)
O40.0221 (7)0.0292 (8)0.0298 (7)−0.0023 (6)0.0050 (6)0.0102 (6)
O50.0175 (6)0.0194 (7)0.0253 (7)0.0012 (5)−0.0005 (5)0.0021 (5)
O60.0368 (8)0.0244 (8)0.0556 (10)0.0038 (6)0.0209 (8)0.0118 (7)
C10.0174 (8)0.0212 (9)0.0128 (8)−0.0003 (7)0.0018 (6)−0.0010 (7)
C20.0128 (8)0.0171 (8)0.0167 (8)−0.0016 (7)0.0006 (6)−0.0001 (6)
C30.0146 (8)0.0165 (9)0.0133 (8)0.0000 (7)0.0028 (6)0.0000 (7)
C40.0153 (8)0.0159 (8)0.0132 (8)0.0026 (7)0.0009 (6)−0.0056 (7)
C50.0152 (8)0.0166 (9)0.0172 (9)0.0016 (7)0.0016 (6)−0.0023 (7)
C60.0209 (9)0.0257 (10)0.0138 (8)0.0023 (8)0.0011 (7)−0.0024 (7)
C70.0352 (10)0.0305 (11)0.0176 (9)0.0017 (9)−0.0064 (8)0.0041 (9)
C80.0276 (11)0.0400 (13)0.0482 (14)0.0029 (10)−0.0139 (9)0.0012 (11)
C90.0263 (10)0.0344 (12)0.0317 (11)−0.0028 (9)−0.0008 (8)−0.0138 (9)
C100.0338 (11)0.0283 (12)0.0586 (15)−0.0064 (10)0.0160 (11)−0.0079 (11)
C110.0174 (8)0.0356 (11)0.0182 (9)0.0039 (8)0.0029 (7)0.0010 (9)
C120.0293 (11)0.0346 (12)0.0271 (11)0.0066 (9)0.0041 (8)−0.0036 (9)
C130.0213 (12)0.0515 (18)0.0234 (15)0.0072 (11)0.0073 (10)−0.0077 (11)
C140.0442 (17)0.046 (2)0.0393 (18)0.0195 (14)0.0118 (13)−0.0025 (14)
C13'0.007 (7)0.045 (12)0.022 (10)−0.005 (6)0.004 (6)0.002 (7)
C14'0.032 (7)0.024 (7)0.050 (8)0.010 (6)−0.009 (6)−0.005 (6)
C150.0265 (10)0.0197 (9)0.0138 (9)−0.0023 (8)0.0025 (7)−0.0008 (7)
C160.0377 (11)0.0240 (10)0.0222 (10)−0.0048 (9)0.0067 (8)−0.0076 (8)
C170.0155 (8)0.0178 (9)0.0281 (10)0.0003 (7)−0.0037 (7)0.0074 (8)
C180.0386 (12)0.0200 (10)0.0382 (13)−0.0062 (9)−0.0003 (10)−0.0018 (8)
C190.0166 (8)0.0230 (10)0.0253 (10)0.0003 (8)−0.0043 (7)0.0008 (8)
C200.0242 (10)0.0332 (12)0.0329 (12)0.0057 (9)0.0033 (8)0.0084 (9)

Geometric parameters (Å, °)

S1—C71.8035 (18)C9—C101.507 (3)
S1—C11.8313 (19)C9—H9A0.9900
S2—C91.807 (2)C9—H9B0.9900
S2—C11.8238 (17)C10—H10A0.9800
S3—C111.814 (2)C10—H10B0.9800
S3—C21.8387 (16)C10—H10C0.9800
S4—C131.806 (2)C11—C121.515 (3)
S4—C13'1.829 (13)C11—H11A0.9900
S4—C31.8348 (16)C11—H11B0.9900
O1—C151.357 (2)C12—H12A0.9800
O1—C41.4510 (19)C12—H12B0.9800
O2—C151.200 (2)C12—H12C0.9800
O3—C171.365 (2)C13—C141.513 (4)
O3—C51.446 (2)C13—H13A0.9900
O4—C171.199 (2)C13—H13B0.9900
O5—C191.352 (2)C14—H14A0.9800
O5—C61.439 (2)C14—H14B0.9800
O6—C191.188 (2)C14—H14C0.9800
C1—C21.539 (2)C13'—C14'1.502 (19)
C1—H11.0000C13'—H13C0.9900
C2—C31.547 (2)C13'—H13D0.9900
C2—H21.0000C14'—H14D0.9800
C3—C41.541 (2)C14'—H14E0.9800
C3—H31.0000C14'—H14F0.9800
C4—C51.524 (2)C15—C161.491 (2)
C4—H41.0000C16—H16A0.9800
C5—C61.527 (2)C16—H16B0.9800
C5—H51.0000C16—H16C0.9800
C6—H6A0.9900C17—C181.496 (3)
C6—H6B0.9900C18—H18A0.9800
C7—C81.524 (3)C18—H18B0.9800
C7—H7A0.9900C18—H18C0.9800
C7—H7B0.9900C19—C201.495 (3)
C8—H8A0.9800C20—H20A0.9800
C8—H8B0.9800C20—H20B0.9800
C8—H8C0.9800C20—H20C0.9800
C7—S1—C1101.38 (9)C9—C10—H10A109.5
C9—S2—C1101.20 (9)C9—C10—H10B109.5
C11—S3—C2102.08 (8)H10A—C10—H10B109.5
C13—S4—C13'32.2 (5)C9—C10—H10C109.5
C13—S4—C3103.66 (10)H10A—C10—H10C109.5
C13'—S4—C3103.3 (4)H10B—C10—H10C109.5
C15—O1—C4118.30 (13)C12—C11—S3114.35 (13)
C17—O3—C5116.06 (13)C12—C11—H11A108.7
C19—O5—C6115.63 (14)S3—C11—H11A108.7
C2—C1—S2110.29 (11)C12—C11—H11B108.7
C2—C1—S1108.94 (11)S3—C11—H11B108.7
S2—C1—S1112.86 (9)H11A—C11—H11B107.6
C2—C1—H1108.2C11—C12—H12A109.5
S2—C1—H1108.2C11—C12—H12B109.5
S1—C1—H1108.2H12A—C12—H12B109.5
C1—C2—C3112.81 (13)C11—C12—H12C109.5
C1—C2—S3107.93 (11)H12A—C12—H12C109.5
C3—C2—S3112.69 (11)H12B—C12—H12C109.5
C1—C2—H2107.7C14—C13—S4113.70 (19)
C3—C2—H2107.7C14—C13—H13A108.8
S3—C2—H2107.7S4—C13—H13A108.8
C4—C3—C2114.75 (13)C14—C13—H13B108.8
C4—C3—S4111.65 (11)S4—C13—H13B108.8
C2—C3—S4108.65 (11)H13A—C13—H13B107.7
C4—C3—H3107.1C14'—C13'—S4117.0 (11)
C2—C3—H3107.1C14'—C13'—H13C108.0
S4—C3—H3107.1S4—C13'—H13C108.0
O1—C4—C5103.41 (12)C14'—C13'—H13D108.0
O1—C4—C3106.83 (13)S4—C13'—H13D108.0
C5—C4—C3116.60 (14)H13C—C13'—H13D107.3
O1—C4—H4109.9C13'—C14'—H14D109.5
C5—C4—H4109.9C13'—C14'—H14E109.5
C3—C4—H4109.9H14D—C14'—H14E109.5
O3—C5—C4107.49 (13)C13'—C14'—H14F109.5
O3—C5—C6108.79 (13)H14D—C14'—H14F109.5
C4—C5—C6113.55 (14)H14E—C14'—H14F109.5
O3—C5—H5109.0O2—C15—O1123.03 (17)
C4—C5—H5109.0O2—C15—C16126.52 (18)
C6—C5—H5109.0O1—C15—C16110.42 (15)
O5—C6—C5109.18 (13)C15—C16—H16A109.5
O5—C6—H6A109.8C15—C16—H16B109.5
C5—C6—H6A109.8H16A—C16—H16B109.5
O5—C6—H6B109.8C15—C16—H16C109.5
C5—C6—H6B109.8H16A—C16—H16C109.5
H6A—C6—H6B108.3H16B—C16—H16C109.5
C8—C7—S1115.40 (14)O4—C17—O3123.77 (18)
C8—C7—H7A108.4O4—C17—C18126.18 (18)
S1—C7—H7A108.4O3—C17—C18110.05 (15)
C8—C7—H7B108.4C17—C18—H18A109.5
S1—C7—H7B108.4C17—C18—H18B109.5
H7A—C7—H7B107.5H18A—C18—H18B109.5
C7—C8—H8A109.5C17—C18—H18C109.5
C7—C8—H8B109.5H18A—C18—H18C109.5
H8A—C8—H8B109.5H18B—C18—H18C109.5
C7—C8—H8C109.5O6—C19—O5124.29 (17)
H8A—C8—H8C109.5O6—C19—C20124.31 (18)
H8B—C8—H8C109.5O5—C19—C20111.37 (16)
C10—C9—S2114.64 (15)C19—C20—H20A109.5
C10—C9—H9A108.6C19—C20—H20B109.5
S2—C9—H9A108.6H20A—C20—H20B109.5
C10—C9—H9B108.6C19—C20—H20C109.5
S2—C9—H9B108.6H20A—C20—H20C109.5
H9A—C9—H9B107.6H20B—C20—H20C109.5
C9—S2—C1—C2−119.35 (13)S4—C3—C4—C5−39.69 (17)
C9—S2—C1—S1118.55 (11)C17—O3—C5—C4153.04 (14)
C7—S1—C1—C2178.77 (11)C17—O3—C5—C6−83.62 (17)
C7—S1—C1—S2−58.37 (11)O1—C4—C5—O3−169.73 (12)
S2—C1—C2—C3169.79 (11)C3—C4—C5—O3−52.85 (18)
S1—C1—C2—C3−65.83 (15)O1—C4—C5—C669.89 (16)
S2—C1—C2—S3−65.04 (13)C3—C4—C5—C6−173.23 (13)
S1—C1—C2—S359.34 (13)C19—O5—C6—C5104.90 (17)
C11—S3—C2—C1134.39 (12)O3—C5—C6—O5−48.42 (19)
C11—S3—C2—C3−100.37 (12)C4—C5—C6—O571.22 (18)
C1—C2—C3—C4176.29 (14)C1—S1—C7—C8−71.74 (18)
S3—C2—C3—C453.74 (17)C1—S2—C9—C1068.51 (17)
C1—C2—C3—S4−57.96 (16)C2—S3—C11—C12−71.05 (15)
S3—C2—C3—S4179.49 (9)C13'—S4—C13—C1418.1 (8)
C13—S4—C3—C4−87.95 (15)C3—S4—C13—C14−75.1 (2)
C13'—S4—C3—C4−121.1 (5)C13—S4—C13'—C14'−38.2 (11)
C13—S4—C3—C2144.51 (13)C3—S4—C13'—C14'56.4 (13)
C13'—S4—C3—C2111.4 (5)C4—O1—C15—O2−4.4 (3)
C15—O1—C4—C5−116.96 (15)C4—O1—C15—C16173.80 (15)
C15—O1—C4—C3119.46 (15)C5—O3—C17—O4−3.9 (2)
C2—C3—C4—O1−160.52 (13)C5—O3—C17—C18175.50 (14)
S4—C3—C4—O175.30 (15)C6—O5—C19—O68.6 (3)
C2—C3—C4—C584.49 (17)C6—O5—C19—C20−169.42 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2804).

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