supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, o2472-o2473    [ doi:10.1107/S1600536808039494 ]

2,3,4,6-Tetra-O-acetyl-[beta]-D-galactopyranosyl 2,3,4,6-tetra-O-acetyl-[beta]-D-glucopyranosyl disulfide tetrahydrofuran solvate

I. Brito, L. Szilágyi and M. López-Rodríguez

Abstract top

The asymmetric unit of title compound, C28H38O18S2·C4H8O, comprises one disulfide-bridged sugar molecule and one solvent molecule. No significant differences in structural parameters are found between the present structure and the previously determined unsolvated form [Brito, López-Rodríguez, Bényei & Szilagyi (2006). Carbohydr. Res. 341, 2967-2972]. The compounds are characterized by a compact structure with spatial proximity of the two pyranosyl rings. One of the carbonyl atoms is disordered over two sites [site occupancy = 0.69 (7) for major component] and the displacement parameters for the THF species are unsually large.

Comment top

The disulfide linkage which plays an essential role in stabilizing the tertiary structure of proteins, was not known in carbohydrate chemistry until recently when it was introduced as a new interglycosidic connecting element (Szilágyi & Varela, 2006). Diglycosyl disulfides were proposed as novel carbohydrate scaffolds with potential biological activity (Szilágyi & Varela, 2006, Chakka et al., 2005). This has recently been demonstrated in binding studies with galectins and in assays with tumor cells (André et al., 2006). We report herein the crystal and molecular structure of the title compound, (I), Fig. 1. The averaged bond lengths [C—O 1.429 (6), O—C 1.341 (8), C=O 1.181 (8), C—C 1.478 (10) Å] and other parameters, Table 1, compare well with those for the previously determined unsolvated form (Brito et al., 2006). The pyranosyl rings adopt chair conformations with Cremer & Pople (1975) puckering parameters: QT = 0.604 (6) (Glc) and 0.566 (5) Å (Gal), θ = 2.4 (5) (Glc) and 9.6 (6)°(Gal), φ = 15 (11) (Glc) and 9(4)° (Gal); these parameters are similar to those for the unsolvated form. The conformations of the acetyl groups are in agreement with the observation that in acetylated pyranoses, the carbonyl C=O bonds tend to align so that they nearly eclipse the axial-H atoms atoms on the common ring C atoms.

Related literature top

For analysis of conformation, see: Cremer & Pople (1975). For the synthesis, see: Szilágyi et al. (2001). For background to disulfide linkage and diglycosyl disulfides, see: André et al. (2006); Chakka et al. (2005); Pérez et al. (1978); Szilágyi & Varela (2006). For the structure of the unsolvated form, see: Brito et al. (2006).

Experimental top

Compound (I) was synthesized as described by Szilágyi et al. (2001).

Refinement top

The H atoms were geometrically placed (C—H = 0.96–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl-C). The O29 atom was refined over two sites using a disorder model, with occupancies of 0.69 (7) and 0.31 (7). The THF molecule is disordered and was modelled with restraints for distances and anisotropic displacement parameters using a 'rigid-bond' restraint to Uij, implemented as the DELU instruction in SHELXL97 (Sheldrick, 2008).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN(Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. All H atoms have been omitted for clarity.
2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl disulfide tetrahydrofuran solvate top
Crystal data top
C28H38O18S2·C4H8OF(000) = 844
Mr = 798.81Dx = 1.281 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4312 reflections
a = 14.6499 (14) Åθ = 2.4–25.0°
b = 10.0096 (10) ŵ = 0.20 mm−1
c = 15.4029 (15) ÅT = 298 K
β = 113.573 (2)°Prism, yellow
V = 2070.2 (4) Å30.40 × 0.30 × 0.20 mm
Z = 2
Data collection top
Nonius KappaCCD area-detector
diffractometer		7410 independent reflections
Radiation source: fine-focus sealed tube4763 reflections with I > 2σ(I)
graphiteRint = 0.046
φ scans, and ω scans with κ offsetsθmax = 25.2°, θmin = 2.5°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		h = −17→16
Tmin = 0.920, Tmax = 0.960k = −12→11
13257 measured reflectionsl = −18→18
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)] = 0.054H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0875P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max = 0.042
7410 reflectionsΔρmax = 0.34 e Å−3
497 parametersΔρmin = −0.19 e Å−3
45 restraintsAbsolute structure: Flack, (1983), 3438 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (9)
Crystal data top
C28H38O18S2·C4H8OV = 2070.2 (4) Å3
Mr = 798.81Z = 2
Monoclinic, P21Mo Kα radiation
a = 14.6499 (14) ŵ = 0.20 mm−1
b = 10.0096 (10) ÅT = 298 K
c = 15.4029 (15) Å0.40 × 0.30 × 0.20 mm
β = 113.573 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer		7410 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		4763 reflections with I > 2σ(I)
Tmin = 0.920, Tmax = 0.960Rint = 0.046
13257 measured reflectionsθmax = 25.2°
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.151Δρmax = 0.34 e Å−3
S = 0.85Δρmin = −0.19 e Å−3
7410 reflectionsAbsolute structure: Flack, (1983), 3438 Friedel pairs
497 parametersFlack parameter: 0.02 (9)
45 restraints
Special details top

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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*/UeqOcc. (<1)
S10.94859 (8)0.98543 (12)0.93468 (8)0.0609 (3)
O10.8235 (2)1.1214 (3)0.98368 (19)0.0587 (7)
O20.5745 (2)1.1063 (3)0.7358 (2)0.0692 (8)
O30.5648 (4)1.2681 (6)0.6357 (3)0.146 (2)
O40.7645 (2)1.0285 (3)0.7398 (2)0.0644 (8)
O50.6752 (4)0.8414 (4)0.7054 (3)0.1135 (14)
O60.8497 (3)1.2956 (4)1.1307 (2)0.0822 (9)
O70.8713 (4)1.0964 (5)1.2001 (3)0.1132 (14)
O80.5850 (2)1.2941 (3)0.8764 (2)0.0684 (8)
O90.5145 (3)1.1965 (4)0.9648 (3)0.1042 (13)
C10.8424 (3)1.0964 (4)0.9008 (3)0.0546 (10)
H10.86121.18140.88090.066*
C20.7471 (3)1.0494 (4)0.8225 (3)0.0548 (10)
H20.72530.96580.84120.066*
C30.6682 (3)1.1554 (4)0.8047 (3)0.0580 (11)
H30.68741.23650.78060.07*
C40.6549 (3)1.1872 (5)0.8953 (3)0.0624 (11)
H40.63011.10830.91660.075*
C50.7552 (3)1.2286 (4)0.9704 (3)0.0601 (11)
H50.77931.30790.94870.072*
C60.5307 (4)1.1702 (7)0.6531 (4)0.0865 (16)
C70.4395 (5)1.1036 (8)0.5895 (4)0.116 (2)
H7A0.38861.11440.61350.174*
H7B0.45241.01020.58590.174*
H7C0.41751.14260.52750.174*
C80.7260 (4)0.9197 (6)0.6875 (4)0.0773 (14)
C90.7533 (5)0.9114 (8)0.6047 (4)0.116 (2)
H9A0.77720.82310.60090.175*
H9B0.80460.97540.61170.175*
H9C0.69590.93020.54780.175*
C100.7520 (4)1.2569 (6)1.0644 (3)0.0802 (15)
H10A0.70491.32821.0580.096*
H10B0.73021.17791.08730.096*
C110.9038 (5)1.2052 (7)1.1941 (4)0.0896 (17)
C121.0060 (5)1.2548 (8)1.2510 (4)0.122 (2)
H12A1.04421.18551.29290.183*
H12B1.00251.33091.28750.183*
H12C1.03741.28011.20940.183*
C130.5199 (3)1.2900 (6)0.9193 (3)0.0704 (12)
C140.4608 (4)1.4138 (5)0.9033 (4)0.0890 (16)
H14A0.40281.39780.91610.133*
H14B0.44081.44170.83860.133*
H14C0.50051.48260.94470.133*
S20.89370 (8)0.80485 (11)0.95029 (7)0.0611 (3)
O210.98609 (19)0.7760 (3)1.13641 (18)0.0584 (7)
O220.7552 (2)0.5961 (3)1.1697 (2)0.0684 (8)
O230.6851 (3)0.7007 (4)1.2553 (3)0.0950 (11)
O240.7182 (2)0.7573 (3)1.0062 (2)0.0678 (8)
O250.6962 (4)0.5714 (5)0.9230 (3)0.1235 (16)
O261.1652 (2)0.8389 (4)1.2729 (2)0.0751 (9)
O271.1690 (4)0.9965 (5)1.3749 (4)0.1336 (17)
O280.9183 (2)0.7190 (4)1.3348 (2)0.0803 (9)
O29A0.988 (5)0.519 (4)1.3922 (18)0.103 (15)0.31 (7)
O29B0.921 (4)0.5063 (16)1.3697 (18)0.155 (9)0.69 (7)
C210.8909 (3)0.8131 (4)1.0674 (3)0.0531 (9)
H210.87390.90371.07990.064*
C220.8144 (3)0.7149 (4)1.0712 (3)0.0576 (10)
H220.82880.6261.05310.069*
C230.8154 (3)0.7094 (5)1.1694 (3)0.0601 (11)
H230.78530.7911.18150.072*
C240.9198 (3)0.6941 (4)1.2442 (3)0.0593 (11)
H240.9430.60281.24240.071*
C250.9914 (3)0.7911 (5)1.2309 (3)0.0593 (10)
H250.9740.88271.24070.071*
C260.6918 (4)0.6043 (5)1.2123 (4)0.0740 (13)
C270.6347 (5)0.4806 (6)1.2017 (5)0.1028 (18)
H27A0.5840.4941.22560.154*
H27B0.67850.41031.23670.154*
H27C0.60420.45661.1360.154*
C280.6681 (4)0.6785 (6)0.9334 (4)0.0798 (14)
C290.5757 (4)0.7449 (7)0.8683 (4)0.105 (2)
H29A0.59180.83060.85020.157*
H29B0.53130.75640.89970.157*
H29C0.54410.69070.81290.157*
C2101.0967 (3)0.7613 (5)1.2966 (3)0.0708 (13)
H21A1.10560.78081.36120.085*
H21B1.11020.66711.29280.085*
C2111.1968 (4)0.9552 (5)1.3177 (4)0.0830 (15)
C2121.2625 (6)1.0235 (7)1.2826 (6)0.128 (2)
H21C1.27371.11321.30670.191*
H21D1.23241.02571.21460.191*
H21E1.32490.97691.30320.191*
C2130.9328 (8)0.6160 (10)1.3954 (5)0.115 (3)
C2140.9212 (7)0.6644 (11)1.4834 (5)0.174 (4)
H21F0.97010.62191.53810.261*
H21G0.85570.64261.47920.261*
H21H0.93040.75951.48880.261*
O310.7418 (11)0.0601 (14)0.3640 (9)0.306 (5)
C310.6827 (15)0.2535 (13)0.4405 (8)0.301 (9)
H31A0.65590.33860.41130.361*
H31B0.710.2650.50870.361*
C320.7705 (12)0.2047 (18)0.4071 (10)0.291 (7)
H32A0.77510.26540.35990.349*
H32B0.83430.2030.46080.349*
C330.6337 (11)0.0251 (15)0.3603 (6)0.235 (5)
H33A0.58780.01380.29470.282*
H33B0.637−0.0590.39270.282*
C340.5917 (12)0.1382 (19)0.4080 (8)0.281 (6)
H34A0.58180.10360.46240.337*
H34B0.52930.17460.3630.337*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0625 (6)0.0635 (6)0.0677 (7)0.0038 (6)0.0377 (5)0.0038 (6)
O10.0704 (18)0.0570 (17)0.0581 (17)0.0048 (13)0.0358 (15)0.0102 (15)
O20.0641 (19)0.0688 (19)0.071 (2)−0.0002 (16)0.0228 (16)−0.0020 (16)
O30.132 (4)0.165 (5)0.098 (3)0.056 (3)0.001 (3)−0.036 (4)
O40.081 (2)0.0657 (19)0.0530 (17)−0.0031 (15)0.0335 (15)−0.0036 (16)
O50.157 (4)0.073 (3)0.121 (3)−0.025 (2)0.066 (3)−0.029 (3)
O60.110 (3)0.070 (2)0.0621 (19)0.0011 (18)0.0296 (19)0.023 (2)
O70.144 (4)0.103 (3)0.106 (3)0.029 (3)0.064 (3)0.023 (3)
O80.0714 (19)0.0543 (17)0.089 (2)0.0138 (16)0.0425 (17)0.0106 (16)
O90.117 (3)0.098 (3)0.135 (3)0.041 (3)0.090 (3)0.031 (2)
C10.063 (3)0.051 (2)0.059 (2)0.004 (2)0.033 (2)0.000 (2)
C20.061 (3)0.053 (2)0.055 (2)0.0059 (19)0.028 (2)−0.002 (2)
C30.056 (3)0.054 (2)0.062 (3)0.002 (2)0.021 (2)−0.002 (2)
C40.063 (3)0.058 (3)0.073 (3)0.011 (2)0.034 (2)0.007 (2)
C50.075 (3)0.048 (2)0.066 (3)0.004 (2)0.037 (2)0.008 (2)
C60.088 (4)0.098 (4)0.071 (4)0.003 (3)0.030 (3)0.001 (3)
C70.092 (4)0.161 (6)0.077 (4)−0.009 (4)0.016 (3)−0.015 (4)
C80.090 (4)0.069 (3)0.067 (3)−0.005 (3)0.025 (3)0.003 (3)
C90.137 (6)0.140 (6)0.069 (4)−0.033 (4)0.039 (4)0.000 (5)
C100.087 (4)0.087 (4)0.071 (3)0.001 (3)0.036 (3)0.020 (3)
C110.125 (5)0.082 (4)0.076 (4)0.014 (3)0.054 (4)0.030 (4)
C120.116 (5)0.149 (7)0.079 (4)0.012 (4)0.017 (4)0.024 (5)
C130.069 (3)0.075 (3)0.074 (3)0.000 (3)0.036 (2)0.006 (3)
C140.084 (4)0.081 (4)0.108 (4)−0.003 (3)0.046 (3)0.013 (3)
S20.0789 (7)0.0549 (6)0.0570 (6)0.0025 (5)0.0350 (5)0.0060 (6)
O210.0597 (17)0.0695 (19)0.0547 (16)0.0044 (13)0.0320 (14)0.0082 (14)
O220.080 (2)0.0643 (18)0.080 (2)−0.0035 (16)0.0514 (18)−0.0061 (17)
O230.105 (3)0.095 (3)0.118 (3)−0.019 (2)0.079 (2)−0.014 (2)
O240.0570 (18)0.079 (2)0.0675 (18)−0.0007 (16)0.0246 (16)0.0021 (16)
O250.129 (4)0.086 (3)0.124 (4)−0.026 (3)0.017 (3)−0.016 (3)
O260.070 (2)0.091 (3)0.0701 (19)−0.0123 (18)0.0342 (16)−0.0047 (18)
O270.186 (5)0.107 (3)0.133 (4)−0.030 (3)0.090 (4)0.005 (4)
O280.095 (2)0.097 (2)0.0640 (19)0.0000 (19)0.0475 (18)0.002 (2)
O29A0.14 (3)0.077 (17)0.066 (10)0.025 (8)0.016 (13)0.010 (13)
O29B0.23 (3)0.128 (9)0.093 (8)0.030 (6)0.052 (14)−0.045 (10)
C210.056 (2)0.054 (2)0.052 (2)0.005 (2)0.0246 (19)0.012 (2)
C220.064 (3)0.055 (2)0.060 (2)0.005 (2)0.031 (2)0.009 (2)
C230.067 (3)0.058 (3)0.068 (3)0.005 (2)0.041 (2)0.010 (2)
C240.078 (3)0.061 (3)0.051 (2)0.006 (2)0.038 (2)0.011 (2)
C250.062 (3)0.069 (3)0.054 (2)0.002 (2)0.031 (2)0.006 (2)
C260.081 (3)0.070 (3)0.092 (3)−0.006 (3)0.055 (3)−0.001 (3)
C270.124 (5)0.090 (4)0.130 (5)−0.011 (4)0.088 (4)−0.024 (4)
C280.074 (4)0.075 (4)0.087 (4)0.000 (3)0.028 (3)−0.024 (3)
C290.073 (3)0.137 (5)0.086 (4)0.028 (4)0.013 (3)−0.014 (4)
C2100.067 (3)0.091 (4)0.062 (3)0.005 (2)0.034 (2)0.007 (3)
C2110.094 (4)0.072 (4)0.082 (4)−0.001 (3)0.035 (3)0.016 (3)
C2120.145 (6)0.086 (4)0.176 (7)−0.019 (4)0.089 (6)−0.021 (4)
C2130.156 (8)0.133 (7)0.066 (4)0.007 (5)0.055 (4)−0.037 (7)
C2140.240 (10)0.230 (11)0.092 (5)−0.013 (6)0.109 (6)−0.051 (8)
O310.397 (14)0.285 (12)0.252 (10)0.024 (9)0.148 (11)0.016 (11)
C310.48 (2)0.171 (9)0.103 (7)0.016 (6)−0.034 (11)0.121 (11)
C320.372 (14)0.227 (12)0.150 (11)0.082 (9)−0.024 (10)0.003 (12)
C330.352 (13)0.214 (10)0.069 (5)0.032 (5)0.011 (7)0.003 (10)
C340.376 (13)0.332 (17)0.094 (7)0.074 (8)0.050 (9)0.126 (12)
Geometric parameters (Å, °) top
S1—C11.810 (4)O24—C221.429 (5)
S1—S22.0313 (16)O25—C281.182 (7)
O1—C51.425 (5)O26—C2111.339 (6)
O1—C11.432 (4)O26—C2101.427 (5)
O2—C61.338 (7)O27—C2111.183 (6)
O2—C31.445 (5)O28—C2131.349 (8)
O3—C61.178 (7)O28—C241.427 (5)
O4—C81.337 (6)O29A—C2131.27 (3)
O4—C21.410 (5)O29B—C2131.156 (17)
O5—C81.187 (6)C21—C221.509 (6)
O6—C111.335 (6)C21—H210.98
O6—C101.440 (6)C22—C231.509 (6)
O7—C111.207 (7)C22—H220.98
O8—C131.361 (5)C23—C241.510 (6)
O8—C41.428 (5)C23—H230.98
O9—C131.191 (6)C24—C251.503 (6)
C1—C21.510 (6)C24—H240.98
C1—H10.98C25—C2101.497 (6)
C2—C31.511 (6)C25—H250.98
C2—H20.98C26—C271.466 (7)
C3—C41.517 (6)C27—H27A0.96
C3—H30.98C27—H27B0.96
C4—C51.520 (6)C27—H27C0.96
C4—H40.98C28—C291.481 (7)
C5—C101.495 (6)C29—H29A0.96
C5—H50.98C29—H29B0.96
C6—C71.463 (8)C29—H29C0.96
C7—H7A0.96C210—H21A0.97
C7—H7B0.96C210—H21B0.97
C7—H7C0.96C211—C2121.450 (9)
C8—C91.484 (8)C212—H21C0.96
C9—H9A0.96C212—H21D0.96
C9—H9B0.96C212—H21E0.96
C9—H9C0.96C213—C2141.513 (9)
C10—H10A0.97C214—H21F0.96
C10—H10B0.97C214—H21G0.96
C11—C121.486 (9)C214—H21H0.96
C12—H12A0.96O31—C321.578 (16)
C12—H12B0.96O31—C331.601 (14)
C12—H12C0.96C31—C321.640 (17)
C13—C141.475 (7)C31—C341.68 (2)
C14—H14A0.96C31—H31A0.97
C14—H14B0.96C31—H31B0.97
C14—H14C0.96C32—H32A0.97
S2—C211.823 (4)C32—H32B0.97
O21—C211.424 (4)C33—C341.601 (15)
O21—C251.434 (4)C33—H33A0.97
O22—C261.337 (5)C33—H33B0.97
O22—C231.437 (5)C34—H34A0.97
O23—C261.196 (6)C34—H34B0.97
O24—C281.326 (6)
C1—S1—S2104.17 (14)C21—C22—C23110.7 (4)
C5—O1—C1112.2 (3)O24—C22—H22109.5
C6—O2—C3119.4 (4)C21—C22—H22109.5
C8—O4—C2118.8 (4)C23—C22—H22109.5
C11—O6—C10117.9 (5)O22—C23—C22105.8 (3)
C13—O8—C4117.6 (3)O22—C23—C24110.7 (4)
O1—C1—C2108.7 (3)C22—C23—C24111.6 (3)
O1—C1—S1107.5 (3)O22—C23—H23109.6
C2—C1—S1116.9 (3)C22—C23—H23109.6
O1—C1—H1107.8C24—C23—H23109.6
C2—C1—H1107.8O28—C24—C25107.8 (3)
S1—C1—H1107.8O28—C24—C23108.8 (3)
O4—C2—C1109.0 (3)C25—C24—C23112.4 (3)
O4—C2—C3110.0 (3)O28—C24—H24109.3
C1—C2—C3108.8 (3)C25—C24—H24109.3
O4—C2—H2109.7C23—C24—H24109.3
C1—C2—H2109.7O21—C25—C210106.7 (3)
C3—C2—H2109.7O21—C25—C24108.2 (3)
O2—C3—C2109.1 (3)C210—C25—C24111.5 (4)
O2—C3—C4108.3 (3)O21—C25—H25110.1
C2—C3—C4110.6 (3)C210—C25—H25110.1
O2—C3—H3109.6C24—C25—H25110.1
C2—C3—H3109.6O23—C26—O22123.2 (5)
C4—C3—H3109.6O23—C26—C27125.0 (4)
O8—C4—C3108.4 (3)O22—C26—C27111.8 (4)
O8—C4—C5110.3 (3)C26—C27—H27A109.5
C3—C4—C5108.4 (3)C26—C27—H27B109.5
O8—C4—H4109.9H27A—C27—H27B109.5
C3—C4—H4109.9C26—C27—H27C109.5
C5—C4—H4109.9H27A—C27—H27C109.5
O1—C5—C10107.2 (3)H27B—C27—H27C109.5
O1—C5—C4108.3 (3)O25—C28—O24123.3 (5)
C10—C5—C4113.1 (4)O25—C28—C29126.1 (6)
O1—C5—H5109.4O24—C28—C29110.6 (5)
C10—C5—H5109.4C28—C29—H29A109.5
C4—C5—H5109.4C28—C29—H29B109.5
O3—C6—O2121.9 (6)H29A—C29—H29B109.5
O3—C6—C7125.7 (6)C28—C29—H29C109.5
O2—C6—C7112.4 (6)H29A—C29—H29C109.5
C6—C7—H7A109.5H29B—C29—H29C109.5
C6—C7—H7B109.5O26—C210—C25111.0 (4)
H7A—C7—H7B109.5O26—C210—H21A109.4
C6—C7—H7C109.5C25—C210—H21A109.4
H7A—C7—H7C109.5O26—C210—H21B109.4
H7B—C7—H7C109.5C25—C210—H21B109.4
O5—C8—O4123.3 (5)H21A—C210—H21B108
O5—C8—C9124.9 (6)O27—C211—O26122.4 (6)
O4—C8—C9111.8 (5)O27—C211—C212126.2 (6)
C8—C9—H9A109.5O26—C211—C212111.2 (5)
C8—C9—H9B109.5C211—C212—H21C109.5
H9A—C9—H9B109.5C211—C212—H21D109.5
C8—C9—H9C109.5H21C—C212—H21D109.5
H9A—C9—H9C109.5C211—C212—H21E109.5
H9B—C9—H9C109.5H21C—C212—H21E109.5
O6—C10—C5109.3 (4)H21D—C212—H21E109.5
O6—C10—H10A109.8O29B—C213—O29A43.8 (10)
C5—C10—H10A109.8O29B—C213—O28121.9 (11)
O6—C10—H10B109.8O29A—C213—O28118.7 (18)
C5—C10—H10B109.8O29B—C213—C214123.7 (11)
H10A—C10—H10B108.3O29A—C213—C214125.3 (12)
O7—C11—O6122.0 (6)O28—C213—C214109.4 (8)
O7—C11—C12126.3 (6)C213—C214—H21F109.5
O6—C11—C12111.6 (6)C213—C214—H21G109.5
C11—C12—H12A109.5H21F—C214—H21G109.5
C11—C12—H12B109.5C213—C214—H21H109.5
H12A—C12—H12B109.5H21F—C214—H21H109.5
C11—C12—H12C109.5H21G—C214—H21H109.5
H12A—C12—H12C109.5C32—O31—C33108.0 (14)
H12B—C12—H12C109.5C32—C31—C34109.3 (9)
O9—C13—O8122.3 (4)C32—C31—H31A109.8
O9—C13—C14125.9 (4)C34—C31—H31A109.8
O8—C13—C14111.8 (5)C32—C31—H31B109.8
C13—C14—H14A109.5C34—C31—H31B109.8
C13—C14—H14B109.5H31A—C31—H31B108.3
H14A—C14—H14B109.5O31—C32—C31107.2 (12)
C13—C14—H14C109.5O31—C32—H32A110.3
H14A—C14—H14C109.5C31—C32—H32A110.3
H14B—C14—H14C109.5O31—C32—H32B110.3
C21—S2—S1104.10 (15)C31—C32—H32B110.3
C21—O21—C25111.7 (3)H32A—C32—H32B108.5
C26—O22—C23120.0 (4)C34—C33—O31112.7 (12)
C28—O24—C22118.2 (4)C34—C33—H33A109.1
C211—O26—C210118.4 (4)O31—C33—H33A109
C213—O28—C24118.9 (5)C34—C33—H33B109.1
O21—C21—C22108.8 (3)O31—C33—H33B109
O21—C21—S2108.9 (2)H33A—C33—H33B107.8
C22—C21—S2108.6 (3)C33—C34—C31102.6 (10)
O21—C21—H21110.2C33—C34—H34A111.2
C22—C21—H21110.2C31—C34—H34A111.3
S2—C21—H21110.2C33—C34—H34B111.2
O24—C22—C21108.6 (3)C31—C34—H34B111.3
O24—C22—C23108.9 (3)H34A—C34—H34B109.2
C5—O1—C1—C2−64.8 (4)S1—S2—C21—C22156.3 (2)
C5—O1—C1—S1167.8 (3)C28—O24—C22—C21116.5 (4)
S2—S1—C1—O174.3 (3)C28—O24—C22—C23−122.8 (4)
S2—S1—C1—C2−48.2 (3)O21—C21—C22—O24176.3 (3)
C8—O4—C2—C1137.4 (4)S2—C21—C22—O24−65.2 (3)
C8—O4—C2—C3−103.4 (4)O21—C21—C22—C2356.8 (4)
O1—C1—C2—O4178.3 (3)S2—C21—C22—C23175.2 (3)
S1—C1—C2—O4−59.9 (4)C26—O22—C23—C22−138.6 (4)
O1—C1—C2—C358.3 (4)C26—O22—C23—C24100.4 (4)
S1—C1—C2—C3−179.9 (3)O24—C22—C23—O2271.7 (4)
C6—O2—C3—C2−118.1 (4)C21—C22—C23—O22−169.0 (3)
C6—O2—C3—C4121.5 (4)O24—C22—C23—C24−167.9 (4)
O4—C2—C3—O265.7 (4)C21—C22—C23—C24−48.5 (5)
C1—C2—C3—O2−175.0 (3)C213—O28—C24—C25−128.2 (6)
O4—C2—C3—C4−175.3 (3)C213—O28—C24—C23109.8 (6)
C1—C2—C3—C4−56.0 (4)O22—C23—C24—O28−75.1 (4)
C13—O8—C4—C3142.4 (4)C22—C23—C24—O28167.4 (4)
C13—O8—C4—C5−99.0 (4)O22—C23—C24—C25165.7 (3)
O2—C3—C4—O8−64.5 (4)C22—C23—C24—C2548.1 (5)
C2—C3—C4—O8175.9 (3)C21—O21—C25—C210−175.0 (4)
O2—C3—C4—C5175.6 (3)C21—O21—C25—C2464.9 (4)
C2—C3—C4—C556.1 (4)O28—C24—C25—O21−174.4 (3)
C1—O1—C5—C10−172.6 (4)C23—C24—C25—O21−54.6 (4)
C1—O1—C5—C465.0 (4)O28—C24—C25—C21068.6 (4)
O8—C4—C5—O1−177.4 (3)C23—C24—C25—C210−171.6 (4)
C3—C4—C5—O1−58.8 (4)C23—O22—C26—O23−3.7 (8)
O8—C4—C5—C1063.9 (5)C23—O22—C26—C27177.8 (4)
C3—C4—C5—C10−177.6 (4)C22—O24—C28—O255.0 (7)
C3—O2—C6—O3−2.4 (8)C22—O24—C28—C29−173.7 (4)
C3—O2—C6—C7176.9 (4)C211—O26—C210—C2593.8 (5)
C2—O4—C8—O52.4 (7)O21—C25—C210—O2652.3 (5)
C2—O4—C8—C9−178.6 (4)C24—C25—C210—O26170.2 (4)
C11—O6—C10—C5−102.8 (5)C210—O26—C211—O27−1.1 (8)
O1—C5—C10—O660.9 (5)C210—O26—C211—C212−177.6 (5)
C4—C5—C10—O6−179.8 (4)C24—O28—C213—O29B−20 (3)
C10—O6—C11—O7−3.9 (7)C24—O28—C213—O29A31 (3)
C10—O6—C11—C12174.3 (4)C24—O28—C213—C214−176.2 (6)
C4—O8—C13—O9−6.1 (7)C33—O31—C32—C315.7 (13)
C4—O8—C13—C14172.9 (4)C34—C31—C32—O31−4.8 (14)
C1—S1—S2—C21−80.25 (19)C32—O31—C33—C34−4.8 (13)
C25—O21—C21—C22−66.6 (4)O31—C33—C34—C311.7 (12)
C25—O21—C21—S2175.1 (3)C32—C31—C34—C331.9 (12)
S1—S2—C21—O21−85.4 (3)
Table 1
Selected geometric parameters (Å, °) top
S1—C11.810 (4)S2—C211.823 (4)
S1—S22.0313 (16)
C1—S1—S2104.17 (14)O1—C1—S1107.5 (3)
C1—S1—S2—C21−80.25 (19)
Acknowledgements top

This study was supported by grants from the Hungarian National Science Fund [OTKA T48713 (to LSz)]. We thank the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the Cambridge Structural Database.

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

André, S., Pei, Z. C., Siebert, H. C., Ramström, O. & Gabius, H. J. (2006). Bioorg. Med. Chem. 14, 6314–6326.

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Brito, I., López-Rodríguez, M., Bényei, A. & Szilagyi, L. (2006). Carbohydr. Res. 341, 2967–2972.

Chakka, N., Johnston, B. D. & Pinto, B. M. (2005). Can. J. Chem. 83, 929–936.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Pérez, S., Stpierre, J. & Marchessault, R. H. (1978). Can. J. Chem. 56, 2866–2871.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Szilágyi, L., Illyés, T. Z. & Herczegh, P. (2001). Tetrahedron Lett. 42, 3901–3903.

Szilágyi, L. & Varela, O. (2006). Curr. Org. Chem. 10, 1745–1770.