Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019770/hb2374sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019770/hb2374Isup2.hkl |
CCDC reference: 651566
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.
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).
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.
For background literature, see: Fowler & Wolf (1986, 1997). For the synthesis, see Pavliak & Kováč (1991).
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.
Fig. 1. The molecular structure of (I), shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). |
C15H19F3O12S | Z = 2 |
Mr = 480.36 | F(000) = 496 |
Triclinic, P1 | Dx = 1.535 Mg m−3 |
Hall symbol: P 1 | Melting point = 394–395 K |
a = 7.885 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.542 (2) Å | Cell parameters from 2166 reflections |
c = 15.629 (4) Å | θ = 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) Å3 | 0.26 × 0.24 × 0.20 mm |
Bruker SMART CCD diffractometer | 4322 independent reflections |
Radiation source: fine-focus sealed tube | 3520 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→6 |
Tmin = 0.940, Tmax = 0.953 | k = −10→9 |
5327 measured reflections | l = −17→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-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 reflections | Δρmax = 0.22 e Å−3 |
647 parameters | Δρmin = −0.27 e Å−3 |
197 restraints | Absolute structure: Flack (1983), 678 Friedel Pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (10) |
C15H19F3O12S | γ = 90.271 (4)° |
Mr = 480.36 | V = 1039.2 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.885 (2) Å | Mo Kα radiation |
b = 8.542 (2) Å | µ = 0.24 mm−1 |
c = 15.629 (4) Å | T = 293 K |
α = 99.103 (4)° | 0.26 × 0.24 × 0.20 mm |
β = 90.958 (4)° |
Bruker SMART CCD diffractometer | 4322 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3520 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.953 | Rint = 0.022 |
5327 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.102 | Δρmax = 0.22 e Å−3 |
S = 1.05 | Δρmin = −0.27 e Å−3 |
4322 reflections | Absolute structure: Flack (1983), 678 Friedel Pairs |
647 parameters | Absolute structure parameter: 0.02 (10) |
197 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | −0.02275 (18) | 0.39160 (14) | 0.59984 (9) | 0.0604 (4) | |
S2 | 0.30286 (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 |
F4 | 0.4851 (15) | 0.9080 (12) | 0.3465 (8) | 0.087 (4) | 0.50 |
F5 | 0.2613 (13) | 0.9564 (11) | 0.4163 (7) | 0.079 (3) | 0.50 |
F6 | 0.4972 (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 |
O1 | 0.3293 (4) | 0.2628 (3) | 0.77341 (18) | 0.0414 (7) | |
O2 | 0.1262 (4) | 0.4414 (3) | 0.7840 (2) | 0.0471 (8) | |
O3 | 0.0199 (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 |
O4 | 0.1010 (4) | 0.2671 (3) | 0.62718 (19) | 0.0450 (8) | |
O5 | −0.1479 (6) | 0.4347 (5) | 0.6611 (3) | 0.0928 (15) | |
O6 | 0.0638 (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 |
O7 | 0.0675 (4) | −0.0513 (3) | 0.59600 (18) | 0.0435 (7) | |
O8 | −0.1597 (5) | −0.1509 (5) | 0.6510 (3) | 0.0739 (11) | |
O9 | 0.3581 (4) | −0.1525 (3) | 0.68326 (19) | 0.0485 (8) | |
O10 | 0.4592 (6) | −0.1711 (5) | 0.5502 (2) | 0.0789 (13) | |
O11 | 0.6069 (4) | 0.1596 (4) | 0.8673 (2) | 0.0589 (9) | |
O12 | 0.8653 (5) | 0.0630 (4) | 0.8535 (2) | 0.0682 (10) | |
O13 | −0.0337 (4) | 0.8573 (3) | 0.09217 (18) | 0.0433 (7) | |
O14 | 0.1755 (4) | 1.0269 (3) | 0.0859 (2) | 0.0490 (8) | |
O15 | 0.3477 (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 |
O16 | 0.1826 (4) | 0.9410 (3) | 0.24162 (19) | 0.0437 (7) | |
O17 | 0.2047 (6) | 1.2164 (4) | 0.2950 (3) | 0.0832 (13) | |
O18 | 0.4455 (5) | 1.0799 (5) | 0.2206 (3) | 0.0852 (13) | |
O19 | 0.2162 (4) | 0.6368 (3) | 0.26959 (18) | 0.0445 (8) | |
O20 | 0.4479 (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) | |
C1 | 0.1529 (6) | 0.2768 (5) | 0.7796 (3) | 0.0400 (11) | |
H1 | 0.1131 | 0.2403 | 0.8322 | 0.048* | |
C2 | 0.0628 (5) | 0.1897 (4) | 0.7007 (3) | 0.0360 (10) | |
H2 | −0.0598 | 0.1909 | 0.7100 | 0.043* | |
C3 | 0.1234 (6) | 0.0205 (5) | 0.6802 (3) | 0.0368 (10) | |
H3 | 0.0768 | −0.0399 | 0.7228 | 0.044* | |
C4 | 0.3146 (6) | 0.0103 (5) | 0.6835 (3) | 0.0388 (10) | |
H4 | 0.3645 | 0.0503 | 0.6341 | 0.047* | |
C5 | 0.3806 (6) | 0.1027 (5) | 0.7684 (3) | 0.0402 (10) | |
H5 | 0.3319 | 0.0581 | 0.8166 | 0.048* | |
C6 | 0.5699 (6) | 0.1050 (6) | 0.7775 (3) | 0.0504 (12) | |
H6A | 0.6152 | −0.0004 | 0.7600 | 0.061* | |
H6B | 0.6192 | 0.1760 | 0.7419 | 0.061* | |
C7 | 0.7565 (6) | 0.1263 (5) | 0.8976 (3) | 0.0462 (11) | |
C8 | 0.7708 (7) | 0.1779 (8) | 0.9924 (3) | 0.0778 (18) | |
H8A | 0.8816 | 0.1528 | 1.0125 | 0.117* | |
H8B | 0.6864 | 0.1242 | 1.0208 | 0.117* | |
H8C | 0.7537 | 0.2903 | 1.0054 | 0.117* | |
C9 | 0.0366 (8) | 0.5174 (6) | 0.8494 (3) | 0.0575 (14) | |
C10 | 0.0188 (7) | 0.6868 (5) | 0.8422 (4) | 0.0613 (14) | |
H10A | −0.0649 | 0.7337 | 0.8821 | 0.092* | |
H10B | −0.0160 | 0.6968 | 0.7842 | 0.092* | |
H10C | 0.1257 | 0.7400 | 0.8557 | 0.092* | |
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 | −0.2336 | 0.4913 | 0.092* | |
H13B | −0.0459 | −0.2972 | 0.4820 | 0.092* | |
H13C | −0.0882 | −0.1277 | 0.4616 | 0.092* | |
C14 | 0.4319 (6) | −0.2312 (6) | 0.6123 (3) | 0.0503 (13) | |
C15 | 0.4722 (8) | −0.3947 (6) | 0.6236 (4) | 0.0735 (17) | |
H15A | 0.4723 | −0.4614 | 0.5681 | 0.110* | |
H15B | 0.3884 | −0.4327 | 0.6594 | 0.110* | |
H15C | 0.5820 | −0.3968 | 0.6508 | 0.110* | |
C16 | 0.1418 (6) | 0.8664 (5) | 0.0881 (3) | 0.0414 (11) | |
H16 | 0.1825 | 0.8001 | 0.0356 | 0.050* | |
C17 | 0.2274 (6) | 0.8213 (5) | 0.1680 (3) | 0.0396 (10) | |
H17 | 0.3507 | 0.8182 | 0.1611 | 0.048* | |
C18 | 0.1624 (6) | 0.6630 (5) | 0.1861 (3) | 0.0395 (11) | |
H18 | 0.2080 | 0.5789 | 0.1428 | 0.047* | |
C19 | −0.0287 (6) | 0.6536 (5) | 0.1815 (3) | 0.0381 (10) | |
H19 | −0.0787 | 0.7218 | 0.2309 | 0.046* | |
C20 | −0.0891 (6) | 0.6993 (5) | 0.0971 (3) | 0.0412 (10) | |
H20 | −0.0416 | 0.6261 | 0.0489 | 0.049* | |
C21 | −0.2793 (6) | 0.6997 (6) | 0.0875 (3) | 0.0502 (12) | |
H21A | −0.3278 | 0.6048 | 0.1043 | 0.060* | |
H21B | −0.3263 | 0.7916 | 0.1236 | 0.060* | |
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 | −0.3842 | 0.5922 | −0.1564 | 0.120* | |
H23B | −0.4715 | 0.7586 | −0.1403 | 0.120* | |
H23C | −0.5823 | 0.6036 | −0.1512 | 0.120* | |
C24 | 0.2547 (7) | 1.0678 (6) | 0.0179 (3) | 0.0561 (13) | |
C25 | 0.2774 (8) | 1.2410 (5) | 0.0276 (4) | 0.0614 (14) | |
H25A | 0.3250 | 1.2682 | −0.0243 | 0.092* | |
H25B | 0.3526 | 1.2760 | 0.0759 | 0.092* | |
H25C | 0.1695 | 1.2916 | 0.0375 | 0.092* | |
C26 | 0.3761 (7) | 1.0261 (6) | 0.3745 (4) | 0.0744 (18) | |
C27 | 0.3637 (7) | 0.5579 (5) | 0.2761 (3) | 0.0469 (12) | |
C28 | 0.4025 (8) | 0.5389 (6) | 0.3675 (3) | 0.0627 (15) | |
H28A | 0.4562 | 0.4385 | 0.3685 | 0.094* | |
H28B | 0.2992 | 0.5431 | 0.3994 | 0.094* | |
H28C | 0.4773 | 0.6228 | 0.3935 | 0.094* | |
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 | −0.1988 | 0.2465 | 0.2934 | 0.107* | |
H30B | −0.1100 | 0.2244 | 0.2034 | 0.107* | |
H30C | −0.3024 | 0.2692 | 0.2098 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0637 (9) | 0.0489 (7) | 0.0696 (9) | 0.0102 (6) | −0.0230 (7) | 0.0150 (6) |
S2 | 0.0620 (9) | 0.0460 (7) | 0.0648 (8) | −0.0196 (6) | −0.0161 (7) | 0.0117 (5) |
F1 | 0.068 (5) | 0.051 (4) | 0.087 (5) | −0.004 (4) | −0.007 (4) | 0.000 (4) |
F2 | 0.096 (6) | 0.082 (5) | 0.074 (5) | 0.006 (4) | −0.012 (4) | 0.001 (4) |
F3 | 0.098 (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) |
F4 | 0.087 (6) | 0.082 (5) | 0.101 (7) | −0.005 (4) | −0.033 (5) | 0.047 (4) |
F5 | 0.096 (6) | 0.078 (6) | 0.065 (5) | 0.011 (5) | −0.013 (4) | 0.014 (4) |
F6 | 0.094 (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) |
O1 | 0.0347 (18) | 0.0427 (16) | 0.0462 (17) | 0.0050 (14) | −0.0028 (14) | 0.0052 (13) |
O2 | 0.056 (2) | 0.0376 (16) | 0.0471 (19) | 0.0096 (15) | 0.0068 (16) | 0.0026 (13) |
O3 | 0.104 (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) |
O4 | 0.0440 (19) | 0.0519 (16) | 0.0411 (17) | 0.0108 (15) | −0.0024 (14) | 0.0139 (14) |
O5 | 0.084 (3) | 0.111 (3) | 0.074 (3) | 0.065 (3) | −0.019 (2) | −0.014 (2) |
O6 | 0.090 (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) |
O7 | 0.0473 (19) | 0.0488 (16) | 0.0327 (15) | −0.0019 (15) | −0.0050 (14) | 0.0020 (13) |
O8 | 0.063 (3) | 0.097 (3) | 0.059 (2) | −0.026 (2) | 0.001 (2) | 0.005 (2) |
O9 | 0.058 (2) | 0.0460 (16) | 0.0414 (17) | 0.0168 (15) | 0.0015 (15) | 0.0066 (14) |
O10 | 0.097 (3) | 0.092 (3) | 0.046 (2) | 0.040 (2) | 0.009 (2) | 0.002 (2) |
O11 | 0.0363 (19) | 0.090 (2) | 0.0448 (19) | 0.0184 (18) | −0.0064 (15) | −0.0054 (16) |
O12 | 0.044 (2) | 0.092 (3) | 0.066 (2) | 0.014 (2) | −0.0028 (18) | 0.006 (2) |
O13 | 0.0420 (19) | 0.0479 (17) | 0.0423 (16) | −0.0030 (14) | −0.0003 (14) | 0.0146 (13) |
O14 | 0.064 (2) | 0.0408 (16) | 0.0437 (18) | −0.0073 (15) | 0.0129 (16) | 0.0115 (13) |
O15 | 0.082 (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) |
O16 | 0.0446 (19) | 0.0471 (16) | 0.0384 (16) | −0.0102 (14) | 0.0014 (14) | 0.0035 (13) |
O17 | 0.098 (3) | 0.043 (2) | 0.105 (3) | −0.003 (2) | −0.035 (3) | 0.0041 (19) |
O18 | 0.065 (3) | 0.091 (3) | 0.103 (3) | −0.042 (2) | 0.003 (2) | 0.026 (2) |
O19 | 0.047 (2) | 0.0536 (17) | 0.0333 (16) | −0.0029 (16) | −0.0033 (14) | 0.0082 (13) |
O20 | 0.074 (3) | 0.113 (3) | 0.062 (2) | 0.038 (3) | 0.002 (2) | 0.025 (2) |
O21 | 0.052 (2) | 0.0489 (18) | 0.0405 (17) | −0.0148 (15) | −0.0002 (15) | 0.0096 (13) |
O22 | 0.104 (3) | 0.094 (3) | 0.044 (2) | −0.032 (2) | 0.015 (2) | 0.009 (2) |
O23 | 0.041 (2) | 0.098 (3) | 0.0454 (18) | −0.0156 (19) | −0.0113 (16) | 0.0230 (17) |
O24 | 0.045 (2) | 0.098 (3) | 0.076 (3) | −0.014 (2) | 0.002 (2) | 0.024 (2) |
C1 | 0.045 (3) | 0.041 (2) | 0.034 (2) | 0.009 (2) | 0.003 (2) | 0.0040 (18) |
C2 | 0.033 (2) | 0.040 (2) | 0.035 (2) | 0.0086 (19) | 0.0017 (19) | 0.0068 (18) |
C3 | 0.038 (3) | 0.041 (2) | 0.030 (2) | 0.001 (2) | −0.0017 (18) | 0.0031 (18) |
C4 | 0.046 (3) | 0.041 (2) | 0.031 (2) | 0.011 (2) | 0.0026 (19) | 0.0074 (18) |
C5 | 0.035 (2) | 0.049 (2) | 0.037 (2) | 0.004 (2) | 0.0025 (19) | 0.0068 (19) |
C6 | 0.041 (3) | 0.069 (3) | 0.039 (3) | 0.014 (2) | 0.002 (2) | 0.003 (2) |
C7 | 0.034 (3) | 0.054 (3) | 0.051 (3) | 0.001 (2) | −0.001 (2) | 0.010 (2) |
C8 | 0.052 (4) | 0.123 (5) | 0.056 (3) | 0.007 (4) | −0.012 (3) | 0.008 (3) |
C9 | 0.071 (4) | 0.046 (3) | 0.056 (3) | 0.011 (3) | 0.016 (3) | 0.007 (2) |
C10 | 0.062 (4) | 0.046 (3) | 0.071 (3) | 0.010 (2) | −0.004 (3) | −0.003 (2) |
C11 | 0.076 (4) | 0.077 (4) | 0.065 (4) | 0.029 (4) | −0.016 (3) | 0.014 (3) |
C12 | 0.056 (3) | 0.033 (2) | 0.050 (3) | 0.004 (2) | −0.008 (3) | 0.005 (2) |
C13 | 0.070 (4) | 0.056 (3) | 0.054 (3) | −0.002 (3) | −0.022 (3) | −0.003 (2) |
C14 | 0.046 (3) | 0.057 (3) | 0.044 (3) | 0.018 (2) | −0.012 (2) | −0.006 (2) |
C15 | 0.072 (4) | 0.065 (3) | 0.077 (4) | 0.024 (3) | −0.014 (3) | −0.010 (3) |
C16 | 0.041 (3) | 0.040 (2) | 0.045 (3) | −0.006 (2) | 0.005 (2) | 0.0086 (19) |
C17 | 0.032 (2) | 0.047 (2) | 0.040 (2) | −0.009 (2) | 0.0052 (19) | 0.0048 (19) |
C18 | 0.047 (3) | 0.041 (2) | 0.030 (2) | −0.002 (2) | 0.0011 (19) | 0.0062 (18) |
C19 | 0.040 (3) | 0.043 (2) | 0.031 (2) | −0.006 (2) | 0.0013 (19) | 0.0060 (18) |
C20 | 0.036 (3) | 0.050 (2) | 0.037 (2) | −0.004 (2) | 0.0010 (19) | 0.0081 (19) |
C21 | 0.041 (3) | 0.071 (3) | 0.040 (3) | −0.014 (2) | 0.000 (2) | 0.014 (2) |
C22 | 0.039 (3) | 0.065 (3) | 0.050 (3) | 0.003 (3) | −0.006 (2) | 0.006 (2) |
C23 | 0.050 (4) | 0.129 (5) | 0.059 (4) | 0.002 (4) | −0.011 (3) | 0.009 (3) |
C24 | 0.062 (4) | 0.058 (3) | 0.051 (3) | −0.004 (3) | 0.012 (3) | 0.016 (3) |
C25 | 0.066 (4) | 0.051 (3) | 0.073 (4) | −0.009 (3) | 0.006 (3) | 0.026 (2) |
C26 | 0.083 (5) | 0.058 (3) | 0.078 (4) | −0.011 (4) | −0.036 (4) | −0.001 (3) |
C27 | 0.055 (3) | 0.042 (2) | 0.046 (3) | 0.003 (2) | −0.005 (2) | 0.012 (2) |
C28 | 0.083 (4) | 0.057 (3) | 0.049 (3) | −0.004 (3) | −0.017 (3) | 0.013 (2) |
C29 | 0.050 (3) | 0.072 (3) | 0.039 (3) | −0.027 (3) | −0.012 (2) | 0.018 (2) |
C30 | 0.069 (4) | 0.076 (4) | 0.075 (4) | −0.027 (3) | −0.011 (3) | 0.031 (3) |
S1—O6 | 1.342 (11) | C2—C3 | 1.512 (5) |
S1—O5 | 1.396 (5) | C2—H2 | 0.9800 |
S1—O6' | 1.489 (13) | C3—C4 | 1.511 (6) |
S1—O4 | 1.551 (3) | C3—H3 | 0.9800 |
S1—C11 | 1.774 (6) | C4—C5 | 1.516 (6) |
S2—O17 | 1.391 (4) | C4—H4 | 0.9800 |
S2—O18 | 1.405 (4) | C5—C6 | 1.497 (6) |
S2—O16 | 1.540 (3) | C5—H5 | 0.9800 |
S2—C26 | 1.805 (6) | C6—H6A | 0.9700 |
F1—C11 | 1.365 (8) | C6—H6B | 0.9700 |
F2—C11 | 1.313 (7) | C7—C8 | 1.479 (7) |
F3—C11 | 1.326 (8) | C8—H8A | 0.9600 |
F1'—C11 | 1.312 (8) | C8—H8B | 0.9600 |
F2'—C11 | 1.341 (8) | C8—H8C | 0.9600 |
F3'—C11 | 1.329 (8) | C9—C10 | 1.476 (7) |
F4—C26 | 1.353 (9) | C10—H10A | 0.9600 |
F5—C26 | 1.318 (9) | C10—H10B | 0.9600 |
F6—C26 | 1.344 (8) | C10—H10C | 0.9600 |
F4'—C26 | 1.332 (9) | C12—C13 | 1.475 (7) |
F5'—C26 | 1.320 (9) | C13—H13A | 0.9600 |
F6'—C26 | 1.331 (8) | C13—H13B | 0.9600 |
O1—C1 | 1.400 (5) | C13—H13C | 0.9600 |
O1—C5 | 1.418 (5) | C14—C15 | 1.471 (7) |
O2—C9 | 1.335 (6) | C15—H15A | 0.9600 |
O2—C1 | 1.413 (5) | C15—H15B | 0.9600 |
O3—C9 | 1.201 (8) | C15—H15C | 0.9600 |
O3'—C9 | 1.213 (8) | C16—C17 | 1.513 (6) |
O4—C2 | 1.449 (5) | C16—H16 | 0.9800 |
O7—C12 | 1.347 (6) | C17—C18 | 1.513 (6) |
O7—C3 | 1.423 (5) | C17—H17 | 0.9800 |
O8—C12 | 1.192 (6) | C18—C19 | 1.509 (6) |
O9—C14 | 1.346 (6) | C18—H18 | 0.9800 |
O9—C4 | 1.433 (5) | C19—C20 | 1.504 (6) |
O10—C14 | 1.189 (6) | C19—H19 | 0.9800 |
O11—C7 | 1.313 (6) | C20—C21 | 1.505 (6) |
O11—C6 | 1.432 (5) | C20—H20 | 0.9800 |
O12—C7 | 1.187 (6) | C21—H21A | 0.9700 |
O13—C16 | 1.388 (5) | C21—H21B | 0.9700 |
O13—C20 | 1.431 (5) | C22—C23 | 1.480 (7) |
O14—C24 | 1.334 (6) | C23—H23A | 0.9599 |
O14—C16 | 1.401 (5) | C23—H23B | 0.9600 |
O15—C24 | 1.208 (9) | C23—H23C | 0.9600 |
O15'—C24 | 1.192 (7) | C24—C25 | 1.473 (7) |
O16—C17 | 1.463 (5) | C25—H25A | 0.9600 |
O19—C27 | 1.358 (6) | C25—H25B | 0.9600 |
O19—C18 | 1.417 (5) | C25—H25C | 0.9600 |
O20—C27 | 1.179 (6) | C27—C28 | 1.489 (7) |
O21—C29 | 1.364 (6) | C28—H28A | 0.9600 |
O21—C19 | 1.428 (5) | C28—H28B | 0.9600 |
O22—C29 | 1.154 (6) | C28—H28C | 0.9600 |
O23—C22 | 1.332 (6) | C29—C30 | 1.465 (7) |
O23—C21 | 1.437 (5) | C30—H30A | 0.9600 |
O24—C22 | 1.185 (6) | C30—H30B | 0.9600 |
C1—C2 | 1.501 (6) | C30—H30C | 0.9600 |
C1—H1 | 0.9800 | ||
O6—S1—O5 | 110.1 (5) | C12—C13—H13B | 109.5 |
O6—S1—O6' | 26.0 (6) | H13A—C13—H13B | 109.5 |
O5—S1—O6' | 133.4 (5) | C12—C13—H13C | 109.5 |
O6—S1—O4 | 110.0 (5) | H13A—C13—H13C | 109.5 |
O5—S1—O4 | 112.4 (2) | H13B—C13—H13C | 109.5 |
O6'—S1—O4 | 103.3 (5) | O10—C14—O9 | 122.4 (4) |
O6—S1—C11 | 118.7 (5) | O10—C14—C15 | 126.6 (5) |
O5—S1—C11 | 104.1 (3) | O9—C14—C15 | 111.0 (5) |
O6'—S1—C11 | 97.2 (5) | C14—C15—H15A | 109.5 |
O4—S1—C11 | 101.25 (19) | C14—C15—H15B | 109.5 |
O17—S2—O18 | 122.0 (3) | H15A—C15—H15B | 109.5 |
O17—S2—O16 | 108.0 (2) | C14—C15—H15C | 109.5 |
O18—S2—O16 | 111.5 (2) | H15A—C15—H15C | 109.5 |
O17—S2—C26 | 106.5 (3) | H15B—C15—H15C | 109.5 |
O18—S2—C26 | 106.6 (3) | O13—C16—O14 | 104.4 (3) |
O16—S2—C26 | 99.8 (2) | O13—C16—C17 | 111.8 (4) |
C1—O1—C5 | 111.4 (3) | O14—C16—C17 | 108.5 (3) |
C9—O2—C1 | 118.7 (4) | O13—C16—H16 | 110.7 |
C2—O4—S1 | 120.0 (3) | O14—C16—H16 | 110.7 |
C12—O7—C3 | 117.9 (4) | C17—C16—H16 | 110.7 |
C14—O9—C4 | 118.0 (4) | O16—C17—C16 | 107.5 (3) |
C7—O11—C6 | 117.6 (4) | O16—C17—C18 | 107.4 (3) |
C16—O13—C20 | 111.3 (3) | C16—C17—C18 | 111.1 (3) |
C24—O14—C16 | 119.3 (4) | O16—C17—H17 | 110.3 |
C17—O16—S2 | 120.6 (3) | C16—C17—H17 | 110.3 |
C27—O19—C18 | 117.8 (3) | C18—C17—H17 | 110.3 |
C29—O21—C19 | 117.6 (4) | O19—C18—C19 | 108.2 (3) |
C22—O23—C21 | 117.5 (4) | O19—C18—C17 | 110.6 (3) |
O1—C1—O2 | 103.3 (3) | C19—C18—C17 | 111.8 (4) |
O1—C1—C2 | 111.8 (3) | O19—C18—H18 | 108.7 |
O2—C1—C2 | 109.2 (3) | C19—C18—H18 | 108.7 |
O1—C1—H1 | 110.7 | C17—C18—H18 | 108.7 |
O2—C1—H1 | 110.7 | O21—C19—C20 | 107.3 (3) |
C2—C1—H1 | 110.7 | O21—C19—C18 | 107.3 (3) |
O4—C2—C1 | 108.8 (3) | C20—C19—C18 | 108.9 (4) |
O4—C2—C3 | 107.5 (3) | O21—C19—H19 | 111.1 |
C1—C2—C3 | 111.0 (3) | C20—C19—H19 | 111.1 |
O4—C2—H2 | 109.8 | C18—C19—H19 | 111.1 |
C1—C2—H2 | 109.8 | O13—C20—C19 | 109.5 (3) |
C3—C2—H2 | 109.8 | O13—C20—C21 | 106.1 (4) |
O7—C3—C4 | 107.7 (3) | C19—C20—C21 | 113.2 (4) |
O7—C3—C2 | 111.0 (3) | O13—C20—H20 | 109.3 |
C4—C3—C2 | 112.0 (3) | C19—C20—H20 | 109.3 |
O7—C3—H3 | 108.7 | C21—C20—H20 | 109.3 |
C4—C3—H3 | 108.7 | O23—C21—C20 | 106.1 (4) |
C2—C3—H3 | 108.7 | O23—C21—H21A | 110.5 |
O9—C4—C3 | 107.7 (3) | C20—C21—H21A | 110.5 |
O9—C4—C5 | 107.1 (3) | O23—C21—H21B | 110.5 |
C3—C4—C5 | 109.3 (3) | C20—C21—H21B | 110.5 |
O9—C4—H4 | 110.9 | H21A—C21—H21B | 108.7 |
C3—C4—H4 | 110.9 | O24—C22—O23 | 123.3 (5) |
C5—C4—H4 | 110.9 | O24—C22—C23 | 125.9 (5) |
O1—C5—C6 | 106.6 (4) | O23—C22—C23 | 110.8 (5) |
O1—C5—C4 | 108.5 (3) | C22—C23—H23A | 109.5 |
C6—C5—C4 | 113.9 (4) | C22—C23—H23B | 109.5 |
O1—C5—H5 | 109.2 | H23A—C23—H23B | 109.5 |
C6—C5—H5 | 109.2 | C22—C23—H23C | 109.5 |
C4—C5—H5 | 109.2 | H23A—C23—H23C | 109.5 |
O11—C6—C5 | 106.0 (4) | H23B—C23—H23C | 109.5 |
O11—C6—H6A | 110.5 | O15'—C24—O15 | 36.5 (7) |
C5—C6—H6A | 110.5 | O15'—C24—O14 | 120.2 (6) |
O11—C6—H6B | 110.5 | O15—C24—O14 | 119.3 (8) |
C5—C6—H6B | 110.5 | O15'—C24—C25 | 126.5 (6) |
H6A—C6—H6B | 108.7 | O15—C24—C25 | 123.7 (8) |
O12—C7—O11 | 123.5 (5) | O14—C24—C25 | 111.0 (4) |
O12—C7—C8 | 125.1 (5) | C24—C25—H25A | 109.5 |
O11—C7—C8 | 111.4 (4) | C24—C25—H25B | 109.5 |
C7—C8—H8A | 109.5 | H25A—C25—H25B | 109.5 |
C7—C8—H8B | 109.5 | C24—C25—H25C | 109.5 |
H8A—C8—H8B | 109.5 | H25A—C25—H25C | 109.5 |
C7—C8—H8C | 109.5 | H25B—C25—H25C | 109.5 |
H8A—C8—H8C | 109.5 | F5—C26—F5' | 20.8 (7) |
H8B—C8—H8C | 109.5 | F5—C26—F6' | 104.4 (8) |
O3—C9—O3' | 35.1 (7) | F5'—C26—F6' | 89.9 (8) |
O3—C9—O2 | 120.2 (6) | F5—C26—F4' | 90.2 (8) |
O3'—C9—O2 | 120.4 (6) | F5'—C26—F4' | 109.9 (9) |
O3—C9—C10 | 125.5 (6) | F6'—C26—F4' | 113.9 (8) |
O3'—C9—C10 | 124.4 (7) | F5—C26—F6 | 131.0 (8) |
O2—C9—C10 | 111.1 (4) | F5'—C26—F6 | 119.6 (8) |
C9—C10—H10A | 109.5 | F6'—C26—F6 | 30.1 (6) |
C9—C10—H10B | 109.5 | F4'—C26—F6 | 96.4 (8) |
H10A—C10—H10B | 109.5 | F5—C26—F4 | 103.6 (8) |
C9—C10—H10C | 109.5 | F5'—C26—F4 | 124.2 (9) |
H10A—C10—H10C | 109.5 | F6'—C26—F4 | 119.5 (8) |
H10B—C10—H10C | 109.5 | F4'—C26—F4 | 17.2 (9) |
F1'—C11—F2 | 80.0 (7) | F6—C26—F4 | 95.3 (8) |
F1'—C11—F3 | 112.8 (10) | F5—C26—S2 | 115.0 (6) |
F2—C11—F3 | 108.5 (8) | F5'—C26—S2 | 108.9 (6) |
F1'—C11—F3' | 108.9 (8) | F6'—C26—S2 | 113.0 (6) |
F2—C11—F3' | 118.0 (9) | F4'—C26—S2 | 117.5 (6) |
F3—C11—F3' | 10.4 (11) | F6—C26—S2 | 104.5 (6) |
F1'—C11—F2' | 110.5 (7) | F4—C26—S2 | 101.5 (6) |
F2—C11—F2' | 30.6 (5) | O20—C27—O19 | 121.8 (4) |
F3—C11—F2' | 97.0 (8) | O20—C27—C28 | 126.7 (5) |
F3'—C11—F2' | 107.4 (8) | O19—C27—C28 | 111.5 (5) |
F1'—C11—F1 | 20.5 (6) | C27—C28—H28A | 109.5 |
F2—C11—F1 | 100.5 (6) | C27—C28—H28B | 109.5 |
F3—C11—F1 | 107.0 (8) | H28A—C28—H28B | 109.5 |
F3'—C11—F1 | 100.0 (8) | C27—C28—H28C | 109.5 |
F2'—C11—F1 | 131.0 (7) | H28A—C28—H28C | 109.5 |
F1'—C11—S1 | 116.8 (6) | H28B—C28—H28C | 109.5 |
F2—C11—S1 | 122.2 (6) | O22—C29—O21 | 123.0 (5) |
F3—C11—S1 | 112.7 (7) | O22—C29—C30 | 126.9 (5) |
F3'—C11—S1 | 108.0 (6) | O21—C29—C30 | 110.1 (5) |
F2'—C11—S1 | 104.7 (6) | C29—C30—H30A | 109.5 |
F1—C11—S1 | 104.2 (5) | C29—C30—H30B | 109.5 |
O8—C12—O7 | 122.1 (4) | H30A—C30—H30B | 109.5 |
O8—C12—C13 | 127.4 (5) | C29—C30—H30C | 109.5 |
O7—C12—C13 | 110.5 (5) | H30A—C30—H30C | 109.5 |
C12—C13—H13A | 109.5 | H30B—C30—H30C | 109.5 |
O6—S1—O4—C2 | 133.4 (5) | O6'—S1—C11—F1 | 178.3 (7) |
O5—S1—O4—C2 | 10.3 (4) | O4—S1—C11—F1 | 73.2 (5) |
O6'—S1—O4—C2 | 159.6 (5) | C3—O7—C12—O8 | 1.5 (6) |
C11—S1—O4—C2 | −100.2 (3) | C3—O7—C12—C13 | −178.9 (4) |
O17—S2—O16—C17 | 140.1 (3) | C4—O9—C14—O10 | −1.2 (7) |
O18—S2—O16—C17 | 3.4 (4) | C4—O9—C14—C15 | 178.5 (4) |
C26—S2—O16—C17 | −108.9 (3) | C20—O13—C16—O14 | −178.5 (3) |
C5—O1—C1—O2 | 179.9 (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—C17 | 121.0 (4) |
C9—O2—C1—C2 | 114.2 (5) | S2—O16—C17—C16 | −96.3 (4) |
S1—O4—C2—C1 | −95.6 (4) | S2—O16—C17—C18 | 144.1 (3) |
S1—O4—C2—C3 | 144.1 (3) | O13—C16—C17—O16 | −65.5 (4) |
O1—C1—C2—O4 | −66.7 (4) | O14—C16—C17—O16 | 49.1 (4) |
O2—C1—C2—O4 | 47.1 (4) | O13—C16—C17—C18 | 51.7 (5) |
O1—C1—C2—C3 | 51.5 (5) | O14—C16—C17—C18 | 166.3 (3) |
O2—C1—C2—C3 | 165.3 (3) | C27—O19—C18—C19 | 145.2 (4) |
C12—O7—C3—C4 | 142.6 (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—C19 | 69.8 (4) |
O4—C2—C3—C4 | 72.4 (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—C3 | 110.9 (4) | C29—O21—C19—C18 | 108.6 (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—O21 | 167.5 (3) |
C2—C3—C4—O9 | 166.9 (3) | O19—C18—C19—C20 | 173.7 (3) |
O7—C3—C4—C5 | 173.3 (3) | C17—C18—C19—C20 | 51.6 (4) |
C2—C3—C4—C5 | 50.9 (5) | C16—O13—C20—C19 | 65.9 (4) |
C1—O1—C5—C6 | −170.4 (3) | C16—O13—C20—C21 | −171.6 (4) |
C1—O1—C5—C4 | 66.5 (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—C21 | 66.3 (5) |
O9—C4—C5—C6 | 65.4 (5) | C18—C19—C20—C21 | −177.8 (4) |
C3—C4—C5—C6 | −178.2 (4) | C22—O23—C21—C20 | 157.2 (4) |
C7—O11—C6—C5 | 159.1 (4) | O13—C20—C21—O23 | 74.3 (4) |
O1—C5—C6—O11 | 74.9 (4) | C19—C20—C21—O23 | −165.6 (4) |
C4—C5—C6—O11 | −165.5 (4) | C21—O23—C22—O24 | 5.2 (7) |
C6—O11—C7—O12 | 5.2 (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—O3 | 20.4 (10) | C16—O14—C24—O15 | −26.4 (11) |
C1—O2—C9—O3' | −20.5 (10) | C16—O14—C24—C25 | 179.7 (4) |
C1—O2—C9—C10 | −178.7 (4) | O17—S2—C26—F5 | 76.1 (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—F2 | 81.2 (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—F2 | 65.9 (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—F3 | 72.0 (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—F6 | 57.5 (6) |
O5—S1—C11—F3' | 62.1 (7) | O16—S2—C26—F6 | 173.6 (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—F4 | 74.9 (7) |
O5—S1—C11—F2' | 176.4 (5) | C18—O19—C27—O20 | 2.0 (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—C30 | 177.5 (4) |
O5—S1—C11—F1 | −43.6 (5) |
Experimental details
Crystal data | |
Chemical formula | C15H19F3O12S |
Mr | 480.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.885 (2), 8.542 (2), 15.629 (4) |
α, β, γ (°) | 99.103 (4), 90.958 (4), 90.271 (4) |
V (Å3) | 1039.2 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.26 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.940, 0.953 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5327, 4322, 3520 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.102, 1.05 |
No. of reflections | 4322 |
No. of parameters | 647 |
No. of restraints | 197 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.27 |
Absolute structure | Flack (1983), 678 Friedel Pairs |
Absolute structure parameter | 0.02 (10) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
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.