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Acta Cryst. (2007). E63, o2833    [ doi:10.1107/S1600536807019770 ]

1,3,4,6-Tetra-O-acetyl-2-(trifluoromethylsulfonyl)-[beta]-D-mannopyranose

H.-Y. Zhu and S.-D. Jiang

Abstract top

Two independent molecules comprise the asymmetric unit of the title compound, C15H19F3O12S, which was synthesized by reacting 1,3,4,6-tetra-O-acetyl-[beta]-D-mannopyranose with trifluoromethanesulfonic anhydride. In one molecule three F atoms and one O of the -SO2CF3 side chains are disordered equally over two positions; in the other molecule the three F atoms are equally disordered over two positions.

Comment top

1,3,4,6-Tetra-O-acetyl-2-trifluoromethansulfonyl-beta-D-mannopyranose (I) (Fowler et al., 1986) is used for the synthesis of 2-deoxy-2-[18F]fluoro-D-glucose (Fowler et al., 1997) which is a widely used radiopharmaceutical for tumor treatment using positron emission tomography (PET). We have prepared (I) from 1,3,4,6-tetra-O-acetyl-beta-D-mannopyranose and in our recently developped process to synthesize 2-deoxy-2-[18F]fluoro-D-glucose using (I) as a staring material, the crystal structure of (I) has been determined. A view of the molecular structure of (I) is shown in Fig. 1. The trifluoromethansulfonyl side chains are disordered in both molecules. With no H bond interactions, the crystal structure must be stablized by van der Waals forces. The absolute configuration of the stereogenic centres are as follows: C1 S, C2 S, C3 S, C4 R, C5 R, C16 S, C17 S, C18 S, C19 R, C20 R.

Related literature top

For background literature, see: Fowler & Wolf (1986, 1997). For the synthesis, see Pavliak & Kováč (1991).

Experimental top

The title compound was synthesized according to the procedure of Pavliak et al. (1991). Crystals of (I) suitable for X-Ray analysis were grown by slow evaporation of a mixture of ethyl acetate (5 ml) and petroleum ether (10 ml) at room temperature over a period of 5 days.

Refinement top

The H atoms were positioned geometrically (C—H = 0.96–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).
1,3,4,6-Tetra-O-acetyl-2-(trifluoromethylsulfonyl)-β-D-mannopyranose top
Crystal data top
C15H19F3O12SZ = 2
Mr = 480.36F(000) = 496
Triclinic, P1Dx = 1.535 Mg m−3
Hall symbol: P 1Melting point = 394–395 K
a = 7.885 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.542 (2) ÅCell parameters from 2166 reflections
c = 15.629 (4) Åθ = 2.6–22.8°
α = 99.103 (4)°µ = 0.24 mm−1
β = 90.958 (4)°T = 293 K
γ = 90.271 (4)°Block, colourless
V = 1039.2 (5) Å30.26 × 0.24 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer		4322 independent reflections
Radiation source: fine-focus sealed tube3520 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→6
Tmin = 0.940, Tmax = 0.953k = −10→9
5327 measured reflectionsl = −17→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)] = 0.041H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0498P)2 + 0.1781P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.003
4322 reflectionsΔρmax = 0.22 e Å−3
647 parametersΔρmin = −0.27 e Å−3
197 restraintsAbsolute structure: Flack (1983), 678 Friedel Pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (10)
Crystal data top
C15H19F3O12Sγ = 90.271 (4)°
Mr = 480.36V = 1039.2 (5) Å3
Triclinic, P1Z = 2
a = 7.885 (2) ÅMo Kα radiation
b = 8.542 (2) ŵ = 0.24 mm−1
c = 15.629 (4) ÅT = 293 K
α = 99.103 (4)°0.26 × 0.24 × 0.20 mm
β = 90.958 (4)°
Data collection top
Bruker SMART CCD
diffractometer		4322 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3520 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 0.953Rint = 0.022
5327 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.102Δρmax = 0.22 e Å−3
S = 1.05Δρmin = −0.27 e Å−3
4322 reflectionsAbsolute structure: Flack (1983), 678 Friedel Pairs
647 parametersFlack parameter: 0.02 (10)
197 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 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) top
xyzUiso*/UeqOcc. (<1)
S1−0.02275 (18)0.39160 (14)0.59984 (9)0.0604 (4)
S20.30286 (17)1.08151 (14)0.27349 (9)0.0575 (4)
F1−0.2372 (11)0.1807 (9)0.5496 (6)0.070 (3)0.50
F2−0.0571 (11)0.1715 (9)0.4551 (5)0.085 (3)0.50
F3−0.2327 (16)0.3640 (14)0.4687 (8)0.098 (5)0.50
F1'−0.2084 (14)0.1471 (9)0.5269 (7)0.095 (4)0.50
F2'−0.0168 (11)0.2427 (12)0.4501 (5)0.097 (3)0.50
F3'−0.2485 (14)0.3694 (12)0.4820 (8)0.079 (4)0.50
F40.4851 (15)0.9080 (12)0.3465 (8)0.087 (4)0.50
F50.2613 (13)0.9564 (11)0.4163 (7)0.079 (3)0.50
F60.4972 (12)1.1337 (10)0.4036 (6)0.088 (3)0.50
F4'0.4747 (16)0.8990 (12)0.3704 (8)0.077 (3)0.50
F5'0.2438 (13)1.0102 (12)0.4231 (7)0.079 (3)0.50
F6'0.4299 (13)1.1494 (11)0.4317 (6)0.087 (3)0.50
O10.3293 (4)0.2628 (3)0.77341 (18)0.0414 (7)
O20.1262 (4)0.4414 (3)0.7840 (2)0.0471 (8)
O30.0199 (15)0.4611 (11)0.9144 (5)0.070 (3)0.50
O3'−0.0585 (14)0.4445 (12)0.8892 (8)0.084 (3)0.50
O40.1010 (4)0.2671 (3)0.62718 (19)0.0450 (8)
O5−0.1479 (6)0.4347 (5)0.6611 (3)0.0928 (15)
O60.0638 (16)0.5204 (12)0.5858 (7)0.072 (3)0.50
O6'0.0854 (18)0.4832 (14)0.5478 (8)0.084 (4)0.50
O70.0675 (4)−0.0513 (3)0.59600 (18)0.0435 (7)
O8−0.1597 (5)−0.1509 (5)0.6510 (3)0.0739 (11)
O90.3581 (4)−0.1525 (3)0.68326 (19)0.0485 (8)
O100.4592 (6)−0.1711 (5)0.5502 (2)0.0789 (13)
O110.6069 (4)0.1596 (4)0.8673 (2)0.0589 (9)
O120.8653 (5)0.0630 (4)0.8535 (2)0.0682 (10)
O13−0.0337 (4)0.8573 (3)0.09217 (18)0.0433 (7)
O140.1755 (4)1.0269 (3)0.0859 (2)0.0490 (8)
O150.3477 (16)0.9738 (15)−0.0237 (9)0.085 (4)0.40
O15'0.2645 (13)0.9757 (9)−0.0476 (4)0.077 (3)0.60
O160.1826 (4)0.9410 (3)0.24162 (19)0.0437 (7)
O170.2047 (6)1.2164 (4)0.2950 (3)0.0832 (13)
O180.4455 (5)1.0799 (5)0.2206 (3)0.0852 (13)
O190.2162 (4)0.6368 (3)0.26959 (18)0.0445 (8)
O200.4479 (6)0.5157 (5)0.2153 (3)0.0816 (12)
O21−0.0754 (4)0.4915 (3)0.18026 (19)0.0470 (8)
O22−0.1672 (6)0.5425 (5)0.3149 (2)0.0806 (12)
O23−0.3150 (4)0.7048 (4)−0.0025 (2)0.0603 (9)
O24−0.5749 (5)0.6116 (5)0.0092 (3)0.0723 (11)
C10.1529 (6)0.2768 (5)0.7796 (3)0.0400 (11)
H10.11310.24030.83220.048*
C20.0628 (5)0.1897 (4)0.7007 (3)0.0360 (10)
H2−0.05980.19090.71000.043*
C30.1234 (6)0.0205 (5)0.6802 (3)0.0368 (10)
H30.0768−0.03990.72280.044*
C40.3146 (6)0.0103 (5)0.6835 (3)0.0388 (10)
H40.36450.05030.63410.047*
C50.3806 (6)0.1027 (5)0.7684 (3)0.0402 (10)
H50.33190.05810.81660.048*
C60.5699 (6)0.1050 (6)0.7775 (3)0.0504 (12)
H6A0.6152−0.00040.76000.061*
H6B0.61920.17600.74190.061*
C70.7565 (6)0.1263 (5)0.8976 (3)0.0462 (11)
C80.7708 (7)0.1779 (8)0.9924 (3)0.0778 (18)
H8A0.88160.15281.01250.117*
H8B0.68640.12421.02080.117*
H8C0.75370.29031.00540.117*
C90.0366 (8)0.5174 (6)0.8494 (3)0.0575 (14)
C100.0188 (7)0.6868 (5)0.8422 (4)0.0613 (14)
H10A−0.06490.73370.88210.092*
H10B−0.01600.69680.78420.092*
H10C0.12570.74000.85570.092*
C11−0.1335 (7)0.2770 (6)0.5116 (3)0.0723 (17)
C12−0.0774 (7)−0.1369 (5)0.5893 (3)0.0465 (12)
C13−0.1140 (7)−0.2048 (6)0.4981 (3)0.0614 (14)
H13A−0.2319−0.23360.49130.092*
H13B−0.0459−0.29720.48200.092*
H13C−0.0882−0.12770.46160.092*
C140.4319 (6)−0.2312 (6)0.6123 (3)0.0503 (13)
C150.4722 (8)−0.3947 (6)0.6236 (4)0.0735 (17)
H15A0.4723−0.46140.56810.110*
H15B0.3884−0.43270.65940.110*
H15C0.5820−0.39680.65080.110*
C160.1418 (6)0.8664 (5)0.0881 (3)0.0414 (11)
H160.18250.80010.03560.050*
C170.2274 (6)0.8213 (5)0.1680 (3)0.0396 (10)
H170.35070.81820.16110.048*
C180.1624 (6)0.6630 (5)0.1861 (3)0.0395 (11)
H180.20800.57890.14280.047*
C19−0.0287 (6)0.6536 (5)0.1815 (3)0.0381 (10)
H19−0.07870.72180.23090.046*
C20−0.0891 (6)0.6993 (5)0.0971 (3)0.0412 (10)
H20−0.04160.62610.04890.049*
C21−0.2793 (6)0.6997 (6)0.0875 (3)0.0502 (12)
H21A−0.32780.60480.10430.060*
H21B−0.32630.79160.12360.060*
C22−0.4661 (6)0.6519 (6)−0.0341 (3)0.0515 (12)
C23−0.4770 (8)0.6516 (8)−0.1288 (4)0.0798 (18)
H23A−0.38420.5922−0.15640.120*
H23B−0.47150.7586−0.14030.120*
H23C−0.58230.6036−0.15120.120*
C240.2547 (7)1.0678 (6)0.0179 (3)0.0561 (13)
C250.2774 (8)1.2410 (5)0.0276 (4)0.0614 (14)
H25A0.32501.2682−0.02430.092*
H25B0.35261.27600.07590.092*
H25C0.16951.29160.03750.092*
C260.3761 (7)1.0261 (6)0.3745 (4)0.0744 (18)
C270.3637 (7)0.5579 (5)0.2761 (3)0.0469 (12)
C280.4025 (8)0.5389 (6)0.3675 (3)0.0627 (15)
H28A0.45620.43850.36850.094*
H28B0.29920.54310.39940.094*
H28C0.47730.62280.39350.094*
C29−0.1476 (6)0.4521 (6)0.2528 (3)0.0532 (13)
C30−0.1937 (8)0.2835 (6)0.2386 (4)0.0713 (16)
H30A−0.19880.24650.29340.107*
H30B−0.11000.22440.20340.107*
H30C−0.30240.26920.20980.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0637 (9)0.0489 (7)0.0696 (9)0.0102 (6)−0.0230 (7)0.0150 (6)
S20.0620 (9)0.0460 (7)0.0648 (8)−0.0196 (6)−0.0161 (7)0.0117 (5)
F10.068 (5)0.051 (4)0.087 (5)−0.004 (4)−0.007 (4)0.000 (4)
F20.096 (6)0.082 (5)0.074 (5)0.006 (4)−0.012 (4)0.001 (4)
F30.098 (8)0.115 (8)0.086 (7)0.024 (6)−0.034 (6)0.031 (5)
F1'0.113 (7)0.054 (5)0.111 (7)0.025 (4)−0.049 (5)−0.009 (4)
F2'0.105 (6)0.121 (7)0.058 (4)0.036 (5)0.001 (4)−0.009 (5)
F3'0.084 (7)0.090 (6)0.065 (5)0.021 (5)−0.038 (5)0.017 (4)
F40.087 (6)0.082 (5)0.101 (7)−0.005 (4)−0.033 (5)0.047 (4)
F50.096 (6)0.078 (6)0.065 (5)0.011 (5)−0.013 (4)0.014 (4)
F60.094 (6)0.081 (5)0.084 (6)−0.023 (4)−0.034 (5)0.000 (4)
F4'0.083 (6)0.085 (6)0.067 (5)0.008 (5)−0.010 (4)0.028 (4)
F5'0.098 (6)0.082 (6)0.060 (5)0.024 (5)0.005 (4)0.020 (4)
F6'0.098 (6)0.084 (5)0.069 (5)−0.006 (5)−0.027 (5)−0.015 (4)
O10.0347 (18)0.0427 (16)0.0462 (17)0.0050 (14)−0.0028 (14)0.0052 (13)
O20.056 (2)0.0376 (16)0.0471 (19)0.0096 (15)0.0068 (16)0.0026 (13)
O30.104 (7)0.063 (5)0.042 (4)0.019 (5)0.013 (4)0.006 (4)
O3'0.088 (7)0.063 (5)0.102 (7)0.008 (5)0.039 (6)0.010 (5)
O40.0440 (19)0.0519 (16)0.0411 (17)0.0108 (15)−0.0024 (14)0.0139 (14)
O50.084 (3)0.111 (3)0.074 (3)0.065 (3)−0.019 (2)−0.014 (2)
O60.090 (6)0.048 (5)0.084 (6)0.001 (4)−0.008 (5)0.026 (4)
O6'0.091 (7)0.079 (6)0.091 (7)−0.004 (5)−0.017 (6)0.048 (5)
O70.0473 (19)0.0488 (16)0.0327 (15)−0.0019 (15)−0.0050 (14)0.0020 (13)
O80.063 (3)0.097 (3)0.059 (2)−0.026 (2)0.001 (2)0.005 (2)
O90.058 (2)0.0460 (16)0.0414 (17)0.0168 (15)0.0015 (15)0.0066 (14)
O100.097 (3)0.092 (3)0.046 (2)0.040 (2)0.009 (2)0.002 (2)
O110.0363 (19)0.090 (2)0.0448 (19)0.0184 (18)−0.0064 (15)−0.0054 (16)
O120.044 (2)0.092 (3)0.066 (2)0.014 (2)−0.0028 (18)0.006 (2)
O130.0420 (19)0.0479 (17)0.0423 (16)−0.0030 (14)−0.0003 (14)0.0146 (13)
O140.064 (2)0.0408 (16)0.0437 (18)−0.0073 (15)0.0129 (16)0.0115 (13)
O150.082 (7)0.080 (6)0.094 (8)−0.001 (6)0.037 (6)0.013 (6)
O15'0.118 (6)0.070 (4)0.042 (4)−0.033 (4)0.016 (4)0.007 (3)
O160.0446 (19)0.0471 (16)0.0384 (16)−0.0102 (14)0.0014 (14)0.0035 (13)
O170.098 (3)0.043 (2)0.105 (3)−0.003 (2)−0.035 (3)0.0041 (19)
O180.065 (3)0.091 (3)0.103 (3)−0.042 (2)0.003 (2)0.026 (2)
O190.047 (2)0.0536 (17)0.0333 (16)−0.0029 (16)−0.0033 (14)0.0082 (13)
O200.074 (3)0.113 (3)0.062 (2)0.038 (3)0.002 (2)0.025 (2)
O210.052 (2)0.0489 (18)0.0405 (17)−0.0148 (15)−0.0002 (15)0.0096 (13)
O220.104 (3)0.094 (3)0.044 (2)−0.032 (2)0.015 (2)0.009 (2)
O230.041 (2)0.098 (3)0.0454 (18)−0.0156 (19)−0.0113 (16)0.0230 (17)
O240.045 (2)0.098 (3)0.076 (3)−0.014 (2)0.002 (2)0.024 (2)
C10.045 (3)0.041 (2)0.034 (2)0.009 (2)0.003 (2)0.0040 (18)
C20.033 (2)0.040 (2)0.035 (2)0.0086 (19)0.0017 (19)0.0068 (18)
C30.038 (3)0.041 (2)0.030 (2)0.001 (2)−0.0017 (18)0.0031 (18)
C40.046 (3)0.041 (2)0.031 (2)0.011 (2)0.0026 (19)0.0074 (18)
C50.035 (2)0.049 (2)0.037 (2)0.004 (2)0.0025 (19)0.0068 (19)
C60.041 (3)0.069 (3)0.039 (3)0.014 (2)0.002 (2)0.003 (2)
C70.034 (3)0.054 (3)0.051 (3)0.001 (2)−0.001 (2)0.010 (2)
C80.052 (4)0.123 (5)0.056 (3)0.007 (4)−0.012 (3)0.008 (3)
C90.071 (4)0.046 (3)0.056 (3)0.011 (3)0.016 (3)0.007 (2)
C100.062 (4)0.046 (3)0.071 (3)0.010 (2)−0.004 (3)−0.003 (2)
C110.076 (4)0.077 (4)0.065 (4)0.029 (4)−0.016 (3)0.014 (3)
C120.056 (3)0.033 (2)0.050 (3)0.004 (2)−0.008 (3)0.005 (2)
C130.070 (4)0.056 (3)0.054 (3)−0.002 (3)−0.022 (3)−0.003 (2)
C140.046 (3)0.057 (3)0.044 (3)0.018 (2)−0.012 (2)−0.006 (2)
C150.072 (4)0.065 (3)0.077 (4)0.024 (3)−0.014 (3)−0.010 (3)
C160.041 (3)0.040 (2)0.045 (3)−0.006 (2)0.005 (2)0.0086 (19)
C170.032 (2)0.047 (2)0.040 (2)−0.009 (2)0.0052 (19)0.0048 (19)
C180.047 (3)0.041 (2)0.030 (2)−0.002 (2)0.0011 (19)0.0062 (18)
C190.040 (3)0.043 (2)0.031 (2)−0.006 (2)0.0013 (19)0.0060 (18)
C200.036 (3)0.050 (2)0.037 (2)−0.004 (2)0.0010 (19)0.0081 (19)
C210.041 (3)0.071 (3)0.040 (3)−0.014 (2)0.000 (2)0.014 (2)
C220.039 (3)0.065 (3)0.050 (3)0.003 (3)−0.006 (2)0.006 (2)
C230.050 (4)0.129 (5)0.059 (4)0.002 (4)−0.011 (3)0.009 (3)
C240.062 (4)0.058 (3)0.051 (3)−0.004 (3)0.012 (3)0.016 (3)
C250.066 (4)0.051 (3)0.073 (4)−0.009 (3)0.006 (3)0.026 (2)
C260.083 (5)0.058 (3)0.078 (4)−0.011 (4)−0.036 (4)−0.001 (3)
C270.055 (3)0.042 (2)0.046 (3)0.003 (2)−0.005 (2)0.012 (2)
C280.083 (4)0.057 (3)0.049 (3)−0.004 (3)−0.017 (3)0.013 (2)
C290.050 (3)0.072 (3)0.039 (3)−0.027 (3)−0.012 (2)0.018 (2)
C300.069 (4)0.076 (4)0.075 (4)−0.027 (3)−0.011 (3)0.031 (3)
Geometric parameters (Å, °) top
S1—O61.342 (11)C2—C31.512 (5)
S1—O51.396 (5)C2—H20.9800
S1—O6'1.489 (13)C3—C41.511 (6)
S1—O41.551 (3)C3—H30.9800
S1—C111.774 (6)C4—C51.516 (6)
S2—O171.391 (4)C4—H40.9800
S2—O181.405 (4)C5—C61.497 (6)
S2—O161.540 (3)C5—H50.9800
S2—C261.805 (6)C6—H6A0.9700
F1—C111.365 (8)C6—H6B0.9700
F2—C111.313 (7)C7—C81.479 (7)
F3—C111.326 (8)C8—H8A0.9600
F1'—C111.312 (8)C8—H8B0.9600
F2'—C111.341 (8)C8—H8C0.9600
F3'—C111.329 (8)C9—C101.476 (7)
F4—C261.353 (9)C10—H10A0.9600
F5—C261.318 (9)C10—H10B0.9600
F6—C261.344 (8)C10—H10C0.9600
F4'—C261.332 (9)C12—C131.475 (7)
F5'—C261.320 (9)C13—H13A0.9600
F6'—C261.331 (8)C13—H13B0.9600
O1—C11.400 (5)C13—H13C0.9600
O1—C51.418 (5)C14—C151.471 (7)
O2—C91.335 (6)C15—H15A0.9600
O2—C11.413 (5)C15—H15B0.9600
O3—C91.201 (8)C15—H15C0.9600
O3'—C91.213 (8)C16—C171.513 (6)
O4—C21.449 (5)C16—H160.9800
O7—C121.347 (6)C17—C181.513 (6)
O7—C31.423 (5)C17—H170.9800
O8—C121.192 (6)C18—C191.509 (6)
O9—C141.346 (6)C18—H180.9800
O9—C41.433 (5)C19—C201.504 (6)
O10—C141.189 (6)C19—H190.9800
O11—C71.313 (6)C20—C211.505 (6)
O11—C61.432 (5)C20—H200.9800
O12—C71.187 (6)C21—H21A0.9700
O13—C161.388 (5)C21—H21B0.9700
O13—C201.431 (5)C22—C231.480 (7)
O14—C241.334 (6)C23—H23A0.9599
O14—C161.401 (5)C23—H23B0.9600
O15—C241.208 (9)C23—H23C0.9600
O15'—C241.192 (7)C24—C251.473 (7)
O16—C171.463 (5)C25—H25A0.9600
O19—C271.358 (6)C25—H25B0.9600
O19—C181.417 (5)C25—H25C0.9600
O20—C271.179 (6)C27—C281.489 (7)
O21—C291.364 (6)C28—H28A0.9600
O21—C191.428 (5)C28—H28B0.9600
O22—C291.154 (6)C28—H28C0.9600
O23—C221.332 (6)C29—C301.465 (7)
O23—C211.437 (5)C30—H30A0.9600
O24—C221.185 (6)C30—H30B0.9600
C1—C21.501 (6)C30—H30C0.9600
C1—H10.9800
O6—S1—O5110.1 (5)C12—C13—H13B109.5
O6—S1—O6'26.0 (6)H13A—C13—H13B109.5
O5—S1—O6'133.4 (5)C12—C13—H13C109.5
O6—S1—O4110.0 (5)H13A—C13—H13C109.5
O5—S1—O4112.4 (2)H13B—C13—H13C109.5
O6'—S1—O4103.3 (5)O10—C14—O9122.4 (4)
O6—S1—C11118.7 (5)O10—C14—C15126.6 (5)
O5—S1—C11104.1 (3)O9—C14—C15111.0 (5)
O6'—S1—C1197.2 (5)C14—C15—H15A109.5
O4—S1—C11101.25 (19)C14—C15—H15B109.5
O17—S2—O18122.0 (3)H15A—C15—H15B109.5
O17—S2—O16108.0 (2)C14—C15—H15C109.5
O18—S2—O16111.5 (2)H15A—C15—H15C109.5
O17—S2—C26106.5 (3)H15B—C15—H15C109.5
O18—S2—C26106.6 (3)O13—C16—O14104.4 (3)
O16—S2—C2699.8 (2)O13—C16—C17111.8 (4)
C1—O1—C5111.4 (3)O14—C16—C17108.5 (3)
C9—O2—C1118.7 (4)O13—C16—H16110.7
C2—O4—S1120.0 (3)O14—C16—H16110.7
C12—O7—C3117.9 (4)C17—C16—H16110.7
C14—O9—C4118.0 (4)O16—C17—C16107.5 (3)
C7—O11—C6117.6 (4)O16—C17—C18107.4 (3)
C16—O13—C20111.3 (3)C16—C17—C18111.1 (3)
C24—O14—C16119.3 (4)O16—C17—H17110.3
C17—O16—S2120.6 (3)C16—C17—H17110.3
C27—O19—C18117.8 (3)C18—C17—H17110.3
C29—O21—C19117.6 (4)O19—C18—C19108.2 (3)
C22—O23—C21117.5 (4)O19—C18—C17110.6 (3)
O1—C1—O2103.3 (3)C19—C18—C17111.8 (4)
O1—C1—C2111.8 (3)O19—C18—H18108.7
O2—C1—C2109.2 (3)C19—C18—H18108.7
O1—C1—H1110.7C17—C18—H18108.7
O2—C1—H1110.7O21—C19—C20107.3 (3)
C2—C1—H1110.7O21—C19—C18107.3 (3)
O4—C2—C1108.8 (3)C20—C19—C18108.9 (4)
O4—C2—C3107.5 (3)O21—C19—H19111.1
C1—C2—C3111.0 (3)C20—C19—H19111.1
O4—C2—H2109.8C18—C19—H19111.1
C1—C2—H2109.8O13—C20—C19109.5 (3)
C3—C2—H2109.8O13—C20—C21106.1 (4)
O7—C3—C4107.7 (3)C19—C20—C21113.2 (4)
O7—C3—C2111.0 (3)O13—C20—H20109.3
C4—C3—C2112.0 (3)C19—C20—H20109.3
O7—C3—H3108.7C21—C20—H20109.3
C4—C3—H3108.7O23—C21—C20106.1 (4)
C2—C3—H3108.7O23—C21—H21A110.5
O9—C4—C3107.7 (3)C20—C21—H21A110.5
O9—C4—C5107.1 (3)O23—C21—H21B110.5
C3—C4—C5109.3 (3)C20—C21—H21B110.5
O9—C4—H4110.9H21A—C21—H21B108.7
C3—C4—H4110.9O24—C22—O23123.3 (5)
C5—C4—H4110.9O24—C22—C23125.9 (5)
O1—C5—C6106.6 (4)O23—C22—C23110.8 (5)
O1—C5—C4108.5 (3)C22—C23—H23A109.5
C6—C5—C4113.9 (4)C22—C23—H23B109.5
O1—C5—H5109.2H23A—C23—H23B109.5
C6—C5—H5109.2C22—C23—H23C109.5
C4—C5—H5109.2H23A—C23—H23C109.5
O11—C6—C5106.0 (4)H23B—C23—H23C109.5
O11—C6—H6A110.5O15'—C24—O1536.5 (7)
C5—C6—H6A110.5O15'—C24—O14120.2 (6)
O11—C6—H6B110.5O15—C24—O14119.3 (8)
C5—C6—H6B110.5O15'—C24—C25126.5 (6)
H6A—C6—H6B108.7O15—C24—C25123.7 (8)
O12—C7—O11123.5 (5)O14—C24—C25111.0 (4)
O12—C7—C8125.1 (5)C24—C25—H25A109.5
O11—C7—C8111.4 (4)C24—C25—H25B109.5
C7—C8—H8A109.5H25A—C25—H25B109.5
C7—C8—H8B109.5C24—C25—H25C109.5
H8A—C8—H8B109.5H25A—C25—H25C109.5
C7—C8—H8C109.5H25B—C25—H25C109.5
H8A—C8—H8C109.5F5—C26—F5'20.8 (7)
H8B—C8—H8C109.5F5—C26—F6'104.4 (8)
O3—C9—O3'35.1 (7)F5'—C26—F6'89.9 (8)
O3—C9—O2120.2 (6)F5—C26—F4'90.2 (8)
O3'—C9—O2120.4 (6)F5'—C26—F4'109.9 (9)
O3—C9—C10125.5 (6)F6'—C26—F4'113.9 (8)
O3'—C9—C10124.4 (7)F5—C26—F6131.0 (8)
O2—C9—C10111.1 (4)F5'—C26—F6119.6 (8)
C9—C10—H10A109.5F6'—C26—F630.1 (6)
C9—C10—H10B109.5F4'—C26—F696.4 (8)
H10A—C10—H10B109.5F5—C26—F4103.6 (8)
C9—C10—H10C109.5F5'—C26—F4124.2 (9)
H10A—C10—H10C109.5F6'—C26—F4119.5 (8)
H10B—C10—H10C109.5F4'—C26—F417.2 (9)
F1'—C11—F280.0 (7)F6—C26—F495.3 (8)
F1'—C11—F3112.8 (10)F5—C26—S2115.0 (6)
F2—C11—F3108.5 (8)F5'—C26—S2108.9 (6)
F1'—C11—F3'108.9 (8)F6'—C26—S2113.0 (6)
F2—C11—F3'118.0 (9)F4'—C26—S2117.5 (6)
F3—C11—F3'10.4 (11)F6—C26—S2104.5 (6)
F1'—C11—F2'110.5 (7)F4—C26—S2101.5 (6)
F2—C11—F2'30.6 (5)O20—C27—O19121.8 (4)
F3—C11—F2'97.0 (8)O20—C27—C28126.7 (5)
F3'—C11—F2'107.4 (8)O19—C27—C28111.5 (5)
F1'—C11—F120.5 (6)C27—C28—H28A109.5
F2—C11—F1100.5 (6)C27—C28—H28B109.5
F3—C11—F1107.0 (8)H28A—C28—H28B109.5
F3'—C11—F1100.0 (8)C27—C28—H28C109.5
F2'—C11—F1131.0 (7)H28A—C28—H28C109.5
F1'—C11—S1116.8 (6)H28B—C28—H28C109.5
F2—C11—S1122.2 (6)O22—C29—O21123.0 (5)
F3—C11—S1112.7 (7)O22—C29—C30126.9 (5)
F3'—C11—S1108.0 (6)O21—C29—C30110.1 (5)
F2'—C11—S1104.7 (6)C29—C30—H30A109.5
F1—C11—S1104.2 (5)C29—C30—H30B109.5
O8—C12—O7122.1 (4)H30A—C30—H30B109.5
O8—C12—C13127.4 (5)C29—C30—H30C109.5
O7—C12—C13110.5 (5)H30A—C30—H30C109.5
C12—C13—H13A109.5H30B—C30—H30C109.5
O6—S1—O4—C2133.4 (5)O6'—S1—C11—F1178.3 (7)
O5—S1—O4—C210.3 (4)O4—S1—C11—F173.2 (5)
O6'—S1—O4—C2159.6 (5)C3—O7—C12—O81.5 (6)
C11—S1—O4—C2−100.2 (3)C3—O7—C12—C13−178.9 (4)
O17—S2—O16—C17140.1 (3)C4—O9—C14—O10−1.2 (7)
O18—S2—O16—C173.4 (4)C4—O9—C14—C15178.5 (4)
C26—S2—O16—C17−108.9 (3)C20—O13—C16—O14−178.5 (3)
C5—O1—C1—O2179.9 (3)C20—O13—C16—C17−61.5 (4)
C5—O1—C1—C2−62.7 (4)C24—O14—C16—O13−119.7 (4)
C9—O2—C1—O1−126.7 (4)C24—O14—C16—C17121.0 (4)
C9—O2—C1—C2114.2 (5)S2—O16—C17—C16−96.3 (4)
S1—O4—C2—C1−95.6 (4)S2—O16—C17—C18144.1 (3)
S1—O4—C2—C3144.1 (3)O13—C16—C17—O16−65.5 (4)
O1—C1—C2—O4−66.7 (4)O14—C16—C17—O1649.1 (4)
O2—C1—C2—O447.1 (4)O13—C16—C17—C1851.7 (5)
O1—C1—C2—C351.5 (5)O14—C16—C17—C18166.3 (3)
O2—C1—C2—C3165.3 (3)C27—O19—C18—C19145.2 (4)
C12—O7—C3—C4142.6 (4)C27—O19—C18—C17−92.0 (4)
C12—O7—C3—C2−94.5 (4)O16—C17—C18—O19−50.8 (5)
O4—C2—C3—O7−48.1 (4)C16—C17—C18—O19−168.1 (4)
C1—C2—C3—O7−167.1 (4)O16—C17—C18—C1969.8 (4)
O4—C2—C3—C472.4 (4)C16—C17—C18—C19−47.4 (5)
C1—C2—C3—C4−46.6 (5)C29—O21—C19—C20−134.5 (4)
C14—O9—C4—C3110.9 (4)C29—O21—C19—C18108.6 (4)
C14—O9—C4—C5−131.6 (4)O19—C18—C19—O21−70.5 (4)
O7—C3—C4—O9−70.7 (4)C17—C18—C19—O21167.5 (3)
C2—C3—C4—O9166.9 (3)O19—C18—C19—C20173.7 (3)
O7—C3—C4—C5173.3 (3)C17—C18—C19—C2051.6 (4)
C2—C3—C4—C550.9 (5)C16—O13—C20—C1965.9 (4)
C1—O1—C5—C6−170.4 (3)C16—O13—C20—C21−171.6 (4)
C1—O1—C5—C466.5 (4)O21—C19—C20—O13−175.5 (3)
O9—C4—C5—O1−176.0 (3)C18—C19—C20—O13−59.7 (4)
C3—C4—C5—O1−59.6 (4)O21—C19—C20—C2166.3 (5)
O9—C4—C5—C665.4 (5)C18—C19—C20—C21−177.8 (4)
C3—C4—C5—C6−178.2 (4)C22—O23—C21—C20157.2 (4)
C7—O11—C6—C5159.1 (4)O13—C20—C21—O2374.3 (4)
O1—C5—C6—O1174.9 (4)C19—C20—C21—O23−165.6 (4)
C4—C5—C6—O11−165.5 (4)C21—O23—C22—O245.2 (7)
C6—O11—C7—O125.2 (7)C21—O23—C22—C23−174.8 (5)
C6—O11—C7—C8−175.1 (4)C16—O14—C24—O15'15.9 (9)
C1—O2—C9—O320.4 (10)C16—O14—C24—O15−26.4 (11)
C1—O2—C9—O3'−20.5 (10)C16—O14—C24—C25179.7 (4)
C1—O2—C9—C10−178.7 (4)O17—S2—C26—F576.1 (6)
O6—S1—C11—F1'176.2 (8)O18—S2—C26—F5−152.2 (6)
O5—S1—C11—F1'−61.0 (7)O16—S2—C26—F5−36.1 (6)
O6'—S1—C11—F1'160.8 (8)O17—S2—C26—F5'54.7 (6)
O4—S1—C11—F1'55.7 (7)O18—S2—C26—F5'−173.7 (6)
O6—S1—C11—F281.2 (8)O16—S2—C26—F5'−57.6 (6)
O5—S1—C11—F2−156.0 (6)O17—S2—C26—F6'−43.6 (7)
O6'—S1—C11—F265.9 (8)O18—S2—C26—F6'88.0 (7)
O4—S1—C11—F2−39.2 (6)O16—S2—C26—F6'−155.9 (6)
O6—S1—C11—F3−50.8 (10)O17—S2—C26—F4'−179.6 (8)
O5—S1—C11—F372.0 (8)O18—S2—C26—F4'−47.9 (8)
O6'—S1—C11—F3−66.1 (9)O16—S2—C26—F4'68.2 (8)
O4—S1—C11—F3−171.2 (7)O17—S2—C26—F6−74.2 (6)
O6—S1—C11—F3'−60.7 (9)O18—S2—C26—F657.5 (6)
O5—S1—C11—F3'62.1 (7)O16—S2—C26—F6173.6 (5)
O6'—S1—C11—F3'−76.1 (8)O17—S2—C26—F4−172.9 (6)
O4—S1—C11—F3'178.8 (7)O18—S2—C26—F4−41.2 (7)
O6—S1—C11—F2'53.6 (8)O16—S2—C26—F474.9 (7)
O5—S1—C11—F2'176.4 (5)C18—O19—C27—O202.0 (6)
O6'—S1—C11—F2'38.2 (7)C18—O19—C27—C28−179.7 (4)
O4—S1—C11—F2'−66.9 (5)C19—O21—C29—O22−2.4 (7)
O6—S1—C11—F1−166.4 (7)C19—O21—C29—C30177.5 (4)
O5—S1—C11—F1−43.6 (5)
references
References top

Bruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

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

Fowler, J. S. & Wolf, A. P. (1986). Appl. Radiat. Isot. 37, 663–668.

Fowler, J. S. & Wolf, A. P. (1997). Acc. Chem. Res. 30, 181–188.

Pavliak, V. & Kováč, P. (1991). Carbohydr. Res. 210, 333–337.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany