1,3,4,6-Tetra-O-acetyl-2-(trifluoro­methyl­sulfon­yl)-β-d-mannopyran­ose

Zhu, H.-Y.; Jiang, S.-D.

doi:10.1107/S1600536807019770

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1,3,4,6-Tetra-O-acetyl-2-(trifluoromethylsulfonyl)-β-D-mannopyranose

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

Two independent molecules comprise the asymmetric unit of the title compound, C₁₅H₁₉F₃O₁₂S, which was synthesized by reacting 1,3,4,6-tetra-O-acetyl-β-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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019770/hb2374sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019770/hb2374Isup2.hkl Contains datablock I

CCDC reference: 651566

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.041
wR factor = 0.102
Data-to-parameter ratio = 6.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.68
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         400 Deg.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        F1'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        F2'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         F3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O3'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O6'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C8
PLAT431_ALERT_2_C Short Inter HL..A Contact  F4'    ..  O10     ..       2.97 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  F5     ..  O10     ..       2.94 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.00 Deg.
              O6   -S1   -O6'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.10 Deg.
              O3   -C9   -O3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      10.40 Deg.
              F3   -C11  -F3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.60 Deg.
              F2   -C11  -F2'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.50 Deg.
              F1'  -C11  -F1      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.50 Deg.
              O15' -C24  -O15     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.80 Deg.
              F5   -C26  -F5'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.10 Deg.
              F6'  -C26  -F6      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      17.20 Deg.
              F4'  -C26  -F4      1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _reflns_number_total               4322
           Count of symmetry unique reflns         3666
           Completeness (_total/calc)            117.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       656
           Fraction of Friedel pairs measured     0.179
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20    = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  27 ALERT level C = Check and explain
  14 ALERT level G = General alerts; check

  16 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  20 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

Structure description top

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

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

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

C₁₅H₁₉F₃O₁₂S	Z = 2
M_r = 480.36	F(000) = 496
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD diffractometer	4322 independent reflections
Radiation source: fine-focus sealed tube	3520 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→6
T_min = 0.940, T_max = 0.953	k = −10→9
5327 measured reflections	l = −17→18

Refinement top

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(F_o²) + (0.0498P)² + 0.1781P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
4322 reflections	Δρ_max = 0.22 e Å⁻³
647 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₉F₃O₁₂S	γ = 90.271 (4)°
M_r = 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)°

Data collection top

Bruker SMART CCD diffractometer	4322 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3520 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.953	R_int = 0.022
5327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.102	Δρ_max = 0.22 e Å⁻³
S = 1.05	Δρ_min = −0.27 e Å⁻³
4322 reflections	Absolute structure: Flack (1983), 678 Friedel Pairs
647 parameters	Absolute structure 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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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)
T_min, T_max	0.940, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	5327, 4322, 3520
R_int	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
Δρ_max, Δρ_min (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.

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1,3,4,6-Tetra-O-acetyl-2-(trifluoro­methyl­sulfon­yl)-β-D-mannopyran­ose