Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C26H38O16S, crystallizes with two unique half mol­ecules in the asymmetric unit, where the central S atom in each of the unique mol­ecules is positioned on a twofold rotation axis. The only major conformational difference between the two mol­ecules concerns one of the acetyl groups. Except for that acetyl group, the atoms of the two different mol­ecules, in an overlay of one mol­ecule on the other, differ on average by only 0.06 (6) Å from each other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047150/sj2366sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047150/sj2366Isup2.hkl
Contains datablock I

CCDC reference: 667263

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.039
  • wR factor = 0.110
  • Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent O Ueq(max)/Ueq(min) ... 4.95 Ratio
Author Response: This is a dynamic disorder of the carbonyl oxygen quite normal for a protected saccharide without strong intermolecular hydrogen bonds. Most probably the whole acetate group is involved in the dynamic disorder but it is most clearly visible at this carbonyl oxygen atom. The movement is perpendicular to the C=O bond direction which is also physically sound.
PLAT220_ALERT_2_A Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       4.87 Ratio
Author Response: This is a dynamic disorder of the carbonyl oxygen quite normal for a protected saccharide without strong intermolecular hydrogen bonds. Most probably the whole acetate group is involved in the dynamic disorder but it is most clearly visible at this carbonyl oxygen atom. The movement is perpendicular to the C=O bond direction which is also physically sound.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for       C16A
Author Response: This is also related to the dynamic disorder of the acetate groups when intermolecular bonding is weak, as it is in this protected saccharide. The C16A is the carbonyl carbon where the oxygen is exhibiting a large movement.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for       C24A
Author Response: This is also related to the dynamic disorder of the acetate groups when intermolecular bonding is weak, as it is in this protected saccharide. The C16A is the carbonyl carbon where the oxygen is exhibiting a large movement.

Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C14A
Author Response: This is also related to the dynamic disorder of the acetate groups when intermolecular bonding is weak, as it is in this protected saccharide. The C16A is the carbonyl carbon where the oxygen is exhibiting a large movement.

Alert level C PLAT213_ALERT_2_C Atom O24B has ADP max/min Ratio ............. 3.60 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio
Author Response: This is a dynamic disorder of the carbonyl oxygen quite normal for a protected saccharide without strong intermolecular hydrogen bonds. Most probably the whole acetate group is involved in the dynamic disorder but it is most clearly visible at this carbonyl oxygen atom. The movement is perpendicular to the C=O bond direction which is also physically sound.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.56 Ratio
Author Response: This is a dynamic disorder of the carbonyl oxygen quite normal for a protected saccharide without strong intermolecular hydrogen bonds. Most probably the whole acetate group is involved in the dynamic disorder but it is most clearly visible at this carbonyl oxygen atom. The movement is perpendicular to the C=O bond direction which is also physically sound.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.60 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C12A
Author Response: This is also related to the dynamic disorder of the acetate groups when intermolecular bonding is weak, as it is in this protected saccharide. The C16A is the carbonyl carbon where the oxygen is exhibiting a large movement.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        O21
Author Response: This is also related to the dynamic disorder of the acetate groups when intermolecular bonding is weak, as it is in this protected saccharide. The C16A is the carbonyl carbon where the oxygen is exhibiting a large movement.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C22A
Author Response: This is also related to the dynamic disorder of the acetate groups when intermolecular bonding is weak, as it is in this protected saccharide. The C16A is the carbonyl carbon where the oxygen is exhibiting a large movement.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C26A
Author Response: This is also related to the dynamic disorder of the acetate groups when intermolecular bonding is weak, as it is in this protected saccharide. The C16A is the carbonyl carbon where the oxygen is exhibiting a large movement.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.992 Tmax scaled 0.992 Tmin scaled 0.942 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 25.68 From the CIF: _reflns_number_total 4492 Count of symmetry unique reflns 3391 Completeness (_total/calc) 132.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1101 Fraction of Friedel pairs measured 0.325 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 C12 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25 = . R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
4 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 13 ALERT level G = General alerts; check 10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 12 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound (I) was synthesized as part of a program towards the synthesis of thioether-linked disaccharides as new glycomimetics (Cumpstey, 2006). The title compound crystallizes with two unique half molecules in the asymmetric unit. Both molecules are shown in Fig. 1. Both of the sulfur atoms are positioned on a two fold axis whereby the second half of each molecule is generated through the two fold rotation. A packing view of the structure is shown in Fig 2. The conformations of the sugar rings in the two molecules are very similar as can be seen from corresponding geometrical parameters for the two rings. The Cremer Pople parameters (Cremer & Pople, 1975) for the ring O15 C11 C12 C13 C14 C15 are: Q=0.587 (3) Å, θ=0.0 (3)° and φ=159 (9)° while for the ring O25 C21 C22 C23 C24 C25 they are: Q=0.597 (3) Å, θ=1.3 (3)° and φ=244 (7)°. Both rings are on C-form. The major conformational difference between the molecules is shown in an overlay of the two unique half molecules (Fig. 3), the acetyl group starting at O16 in one of the molecules deviates significantly from the corresponding acetyl group, beginning with O26 in the other molecule. The rest of the atoms, except for these two acetyl groups, have an average deviation of 0.06 (6)Å between the atoms of one residue and the overlaid residue.

Related literature top

For general background, see: Cumpstey (2006). For synthesis of the trifluoromethanesulfonate precursor to the title compound, see: Grandjean & Lukacs (1996). For geometrical calculations, see: Cremer & Pople (1975); Norrestam (1991).

Experimental top

The title compound (I) was prepared from the trifluoromethanesulfonate derivative (III) (Grandjean & Lukacs, 1996) as follows: sodium sulfide nonahydrate (475 mg, 2.0 mmol) was dried by heating under vacuum and then allowed to cool to RT. Molecular sieves 4Å (ca 500 mg) and acetonitrile (6 ml) were added, followed by trifluoromethanesulfonate (III) (500 mg, 1.0 mmol). The mixture was stirred at 50°C for 3 h, after which time it was diluted with dichloromethane (50 ml) and filtered through Celite. The filtrate was washed with HCl (1M, 50 ml) then NaHCO3 (sat. 50 ml), then dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (3:1 pentane:ethyl acetate) to give the thioether (II) (331 mg, 90%). Thioether (II) (214 mg) was dissolved in THF (3 ml) and cooled to -78 C, while ammonia (ca 20 ml) was condensed in. Sodium (ca 140 mg) was added to give a deep blue solution, followed by MeOH (0.04 ml). After 2 min, NH4Cl was added until the blue colour disappeared and the solvents were allowed to evaporate. The crude material was then acetylated with acetic anhydride (3 + 1.6 ml) and pyridine (3 + 1.6 ml) overnight. Methanol (8 ml) and ethyl acetate (40 ml) were then added and the mixture was washed with HCl (1M, 30 ml) then NaHCO3 (sat. 30 ml), then dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (2:1 toluene:ethyl acetate) to give the title compound (I) (131 mg, 71%). Crystals were grown from methanol solution by slow evaporation of the solvent.

Refinement top

Several of the O-acyl groups showed substantial disorder most clearly shown by the elongated ellipsoids especially of O14B, O16B and O24B. This disorder most probably occurs due to the absence of strong intermolecular hydrogen bonding interactions. Attempts to model the disorder did not improve the fit, thus it is represented only by the elongated ellipsoids. All hydrogen atoms were geometrically positioned and refined with riding motion, d(C—H)=0.96, 0.97,0.98 Å for CH3, CH2 and CH respectivly. The Uiso(H) = 1.5Ueq(C) for CH3 and 1.2Ueq(C) for CH2 and CH. The transformation for the overlay (Fig. 3) was calculated with the program ROTERA (Norrestam, 1991).

Structure description top

The title compound (I) was synthesized as part of a program towards the synthesis of thioether-linked disaccharides as new glycomimetics (Cumpstey, 2006). The title compound crystallizes with two unique half molecules in the asymmetric unit. Both molecules are shown in Fig. 1. Both of the sulfur atoms are positioned on a two fold axis whereby the second half of each molecule is generated through the two fold rotation. A packing view of the structure is shown in Fig 2. The conformations of the sugar rings in the two molecules are very similar as can be seen from corresponding geometrical parameters for the two rings. The Cremer Pople parameters (Cremer & Pople, 1975) for the ring O15 C11 C12 C13 C14 C15 are: Q=0.587 (3) Å, θ=0.0 (3)° and φ=159 (9)° while for the ring O25 C21 C22 C23 C24 C25 they are: Q=0.597 (3) Å, θ=1.3 (3)° and φ=244 (7)°. Both rings are on C-form. The major conformational difference between the molecules is shown in an overlay of the two unique half molecules (Fig. 3), the acetyl group starting at O16 in one of the molecules deviates significantly from the corresponding acetyl group, beginning with O26 in the other molecule. The rest of the atoms, except for these two acetyl groups, have an average deviation of 0.06 (6)Å between the atoms of one residue and the overlaid residue.

For general background, see: Cumpstey (2006). For synthesis of the trifluoromethanesulfonate precursor to the title compound, see: Grandjean & Lukacs (1996). For geometrical calculations, see: Cremer & Pople (1975); Norrestam (1991).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The two unique molecules of (I). Both sulfur atoms lie on twofold rotation axes so that the labelled atoms are related to the unlabelled atoms by the symmetry operations [-x,y,-z + 1] for the upper molecule and [-x + 1,y,-z] for the lower molecule. Displacement ellipsoids are drawn at the 50% level. Hydrogen atoms shown as small circles of arbitrary radii.
[Figure 2] Fig. 2. Packing view of (I) along the b axis.
[Figure 3] Fig. 3. Stereoview of an overlay of the two unique half molecules of the title compound. The yellow atom is the central sulfur atom of each complete molecule while the red or blue atoms designate each unique residue. The two residues differ from each other only after the C16/C26 and the atoms in the acetyl group attached to C16/C26.
[Figure 4] Fig. 4. The formation of the title compound.
Bis(methyl 2,4,6-tri-O-acetyl-β-D-allofuranosid-3-yl)sulfane top
Crystal data top
C26H38O16SF(000) = 1352
Mr = 638.62Dx = 1.292 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 5794 reflections
a = 22.6458 (13) Åθ = 3.8–32.1°
b = 7.2018 (3) ŵ = 0.17 mm1
c = 21.3260 (12) ÅT = 293 K
β = 109.258 (7)°Prism, colourless
V = 3283.4 (3) Å30.30 × 0.05 × 0.05 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur-II with Sapphire-III CCD
diffractometer
4492 independent reflections
Radiation source: Enhance (Mo) X-ray Source3486 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 16.5467 pixels mm-1θmax = 25.7°, θmin = 3.9°
ω scans at different θh = 2725
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 58
Tmin = 0.95, Tmax = 1.00l = 2526
10820 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0718P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.24 e Å3
4492 reflectionsΔρmin = 0.27 e Å3
398 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0036 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1101 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (9)
Crystal data top
C26H38O16SV = 3283.4 (3) Å3
Mr = 638.62Z = 4
Monoclinic, C2Mo Kα radiation
a = 22.6458 (13) ŵ = 0.17 mm1
b = 7.2018 (3) ÅT = 293 K
c = 21.3260 (12) Å0.30 × 0.05 × 0.05 mm
β = 109.258 (7)°
Data collection top
Oxford Diffraction Xcalibur-II with Sapphire-III CCD
diffractometer
4492 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
3486 reflections with I > 2σ(I)
Tmin = 0.95, Tmax = 1.00Rint = 0.021
10820 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.110Δρmax = 0.24 e Å3
S = 1.05Δρmin = 0.27 e Å3
4492 reflectionsAbsolute structure: Flack (1983), 1101 Friedel pairs
398 parametersAbsolute structure parameter: 0.03 (9)
1 restraint
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*/Ueq
S10.00000.92953 (13)0.50000.0534 (3)
C130.06297 (12)0.7707 (4)0.49958 (13)0.0444 (6)
H130.04470.65450.47770.053*
C140.10871 (13)0.7272 (4)0.56881 (13)0.0473 (7)
H140.13960.63800.56390.057*
C150.14320 (13)0.8986 (5)0.60214 (13)0.0520 (7)
H150.11310.98930.60780.062*
O150.17528 (8)0.9763 (3)0.56093 (9)0.0549 (5)
C110.13600 (12)1.0308 (4)0.49624 (13)0.0479 (7)
H110.10641.12680.49920.057*
C120.10163 (12)0.8597 (4)0.46103 (13)0.0465 (7)
H120.13240.76920.45670.056*
O140.07742 (10)0.6447 (3)0.61058 (10)0.0607 (6)
C14A0.08051 (18)0.4616 (6)0.6179 (2)0.0791 (10)
O14B0.1048 (3)0.3678 (5)0.5886 (3)0.173 (2)
C14C0.0512 (3)0.3921 (8)0.6656 (3)0.127 (2)
H14A0.03960.26430.65610.191*
H14B0.01460.46430.66200.191*
H14C0.08040.40240.70990.191*
C160.19207 (16)0.8600 (6)0.66876 (16)0.0745 (10)
H16A0.21400.97380.68690.089*
H16B0.17220.81320.69950.089*
O160.23542 (11)0.7255 (5)0.66035 (11)0.0822 (8)
C16A0.2510 (2)0.5855 (8)0.6984 (2)0.1022 (15)
O16B0.2344 (4)0.5756 (11)0.7444 (3)0.272 (5)
C16C0.2925 (2)0.4510 (10)0.6811 (3)0.1246 (19)
H16C0.33510.49240.69920.187*
H16D0.28100.44160.63370.187*
H16E0.28850.33160.69930.187*
O110.17385 (10)1.0956 (4)0.46204 (11)0.0665 (6)
C11A0.1962 (3)1.2802 (7)0.4788 (3)0.1078 (17)
H11A0.16221.36610.46250.162*
H11B0.22761.30730.45890.162*
H11C0.21401.29140.52620.162*
O120.06299 (9)0.9156 (3)0.39597 (9)0.0605 (6)
C12A0.05499 (17)0.7933 (6)0.34735 (16)0.0647 (9)
O12B0.07856 (16)0.6436 (5)0.35551 (13)0.1047 (10)
C12C0.0102 (2)0.8648 (7)0.28403 (17)0.0952 (14)
H12A0.00150.76910.25090.143*
H12B0.02810.97010.26940.143*
H12C0.02800.90120.29100.143*
S20.50000.97527 (14)0.00000.0504 (3)
C230.46337 (14)0.8177 (4)0.04313 (13)0.0484 (7)
H230.48890.70500.05550.058*
C240.39672 (15)0.7633 (4)0.00179 (14)0.0545 (8)
H240.38070.67560.02740.065*
C250.35471 (13)0.9327 (5)0.01386 (14)0.0555 (7)
H250.37061.02340.03860.067*
O250.35581 (8)1.0108 (3)0.04826 (9)0.0588 (6)
C210.41579 (12)1.0751 (5)0.08979 (13)0.0510 (7)
H210.43161.17370.06790.061*
C220.45988 (13)0.9110 (5)0.10616 (13)0.0495 (7)
H220.44470.82040.13150.059*
O210.40895 (10)1.1376 (4)0.14776 (10)0.0702 (7)
C21A0.3779 (2)1.3135 (9)0.1412 (2)0.124 (2)
H21A0.40721.41110.14240.186*
H21B0.36161.32960.17710.186*
H21C0.34421.31770.09970.186*
O220.52012 (8)0.9780 (3)0.14720 (8)0.0509 (5)
C22A0.55538 (16)0.8637 (6)0.19447 (15)0.0627 (9)
O22B0.53879 (16)0.7114 (5)0.20135 (15)0.1117 (11)
C22C0.61622 (14)0.9470 (7)0.23186 (15)0.0776 (11)
H22A0.62870.90630.27720.116*
H22B0.61261.07980.23020.116*
H22C0.64700.90900.21250.116*
O240.39636 (12)0.6743 (3)0.05891 (11)0.0684 (6)
C24A0.3899 (2)0.4933 (6)0.06424 (18)0.0844 (11)
O24B0.3825 (4)0.4096 (5)0.0215 (2)0.248 (4)
C24C0.3930 (3)0.4115 (7)0.1262 (2)0.1039 (14)
H24A0.39880.27970.12080.156*
H24B0.42740.46470.13680.156*
H24C0.35470.43660.16160.156*
C260.28733 (15)0.8875 (6)0.05192 (17)0.0718 (10)
H26A0.28540.81410.09070.086*
H26B0.27010.81360.02410.086*
O260.25050 (9)1.0513 (4)0.07258 (10)0.0655 (6)
C26A0.24722 (15)1.1191 (6)0.13217 (16)0.0696 (10)
O26B0.27403 (14)1.0533 (6)0.16579 (13)0.1082 (11)
C26C0.2064 (2)1.2840 (9)0.1493 (2)0.1140 (19)
H26C0.20381.32690.19280.171*
H26D0.22361.38050.11740.171*
H26E0.16541.25200.14890.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0376 (5)0.0389 (6)0.0859 (7)0.0000.0233 (5)0.000
C130.0406 (14)0.0391 (15)0.0542 (15)0.0011 (12)0.0165 (13)0.0042 (13)
C140.0430 (15)0.0508 (17)0.0515 (15)0.0151 (13)0.0202 (13)0.0019 (14)
C150.0488 (15)0.061 (2)0.0486 (15)0.0013 (15)0.0193 (13)0.0055 (14)
O150.0415 (9)0.0675 (14)0.0551 (11)0.0040 (10)0.0153 (8)0.0043 (11)
C110.0423 (14)0.0547 (18)0.0510 (15)0.0002 (13)0.0211 (13)0.0010 (14)
C120.0439 (15)0.0516 (17)0.0445 (14)0.0054 (13)0.0154 (12)0.0029 (13)
O140.0732 (13)0.0534 (14)0.0690 (12)0.0163 (11)0.0415 (11)0.0114 (11)
C14A0.097 (3)0.051 (2)0.107 (3)0.014 (2)0.059 (2)0.012 (2)
O14B0.297 (6)0.0479 (18)0.278 (5)0.008 (3)0.233 (5)0.002 (3)
C14C0.173 (5)0.080 (3)0.176 (5)0.033 (3)0.120 (4)0.059 (4)
C160.070 (2)0.094 (3)0.0546 (19)0.008 (2)0.0140 (17)0.009 (2)
O160.0631 (14)0.117 (2)0.0610 (13)0.0220 (15)0.0127 (12)0.0186 (16)
C16A0.123 (4)0.104 (4)0.086 (3)0.003 (3)0.043 (3)0.030 (3)
O16B0.424 (10)0.215 (7)0.290 (7)0.180 (7)0.271 (8)0.177 (6)
C16C0.123 (4)0.121 (5)0.118 (3)0.048 (4)0.023 (3)0.018 (4)
O110.0615 (13)0.0736 (16)0.0782 (13)0.0127 (12)0.0416 (11)0.0053 (13)
C11A0.131 (4)0.090 (3)0.133 (4)0.048 (3)0.085 (3)0.014 (3)
O120.0692 (12)0.0607 (14)0.0450 (11)0.0031 (11)0.0101 (9)0.0033 (11)
C12A0.074 (2)0.073 (3)0.0491 (18)0.009 (2)0.0232 (17)0.0021 (18)
O12B0.138 (3)0.097 (3)0.0672 (15)0.026 (2)0.0173 (16)0.0258 (17)
C12C0.115 (3)0.100 (3)0.057 (2)0.021 (3)0.011 (2)0.004 (2)
S20.0613 (6)0.0382 (5)0.0579 (6)0.0000.0282 (5)0.000
C230.0598 (18)0.0373 (16)0.0488 (15)0.0016 (13)0.0190 (14)0.0019 (13)
C240.071 (2)0.0448 (17)0.0457 (15)0.0159 (16)0.0166 (15)0.0003 (14)
C250.0516 (15)0.061 (2)0.0480 (15)0.0126 (15)0.0085 (13)0.0003 (15)
O250.0420 (10)0.0770 (16)0.0533 (11)0.0082 (10)0.0100 (9)0.0079 (11)
C210.0415 (15)0.0599 (18)0.0476 (15)0.0003 (14)0.0093 (12)0.0031 (14)
C220.0518 (15)0.0502 (17)0.0466 (14)0.0089 (14)0.0164 (12)0.0023 (14)
O210.0554 (12)0.097 (2)0.0535 (11)0.0139 (13)0.0119 (10)0.0157 (12)
C21A0.102 (3)0.154 (5)0.091 (3)0.076 (4)0.001 (3)0.036 (3)
O220.0438 (9)0.0566 (12)0.0459 (9)0.0004 (10)0.0060 (8)0.0055 (10)
C22A0.066 (2)0.076 (3)0.0431 (16)0.0171 (19)0.0140 (16)0.0132 (17)
O22B0.119 (2)0.087 (2)0.100 (2)0.007 (2)0.0042 (18)0.044 (2)
C22C0.0615 (19)0.111 (3)0.0533 (17)0.012 (2)0.0090 (15)0.004 (2)
O240.1048 (17)0.0452 (13)0.0560 (11)0.0225 (12)0.0276 (12)0.0062 (10)
C24A0.143 (3)0.047 (2)0.066 (2)0.011 (2)0.037 (2)0.0012 (19)
O24B0.606 (13)0.048 (2)0.171 (4)0.011 (4)0.237 (6)0.003 (3)
C24C0.156 (4)0.069 (3)0.088 (3)0.025 (3)0.042 (3)0.024 (2)
C260.062 (2)0.074 (3)0.068 (2)0.0157 (19)0.0062 (17)0.0081 (19)
O260.0550 (12)0.0881 (17)0.0511 (11)0.0059 (12)0.0145 (9)0.0006 (12)
C26A0.062 (2)0.091 (3)0.0586 (19)0.0005 (19)0.0241 (17)0.0071 (19)
O26B0.126 (2)0.138 (3)0.0759 (16)0.043 (2)0.0538 (17)0.0097 (18)
C26C0.118 (4)0.132 (5)0.106 (3)0.047 (4)0.055 (3)0.041 (3)
Geometric parameters (Å, º) top
S1—C13i1.831 (3)S2—C231.824 (3)
S1—C131.831 (3)S2—C23ii1.824 (3)
C13—C121.526 (4)C23—C241.527 (4)
C13—C141.530 (4)C23—C221.528 (4)
C13—H130.9800C23—H230.9800
C14—O141.437 (3)C24—O241.442 (4)
C14—C151.508 (5)C24—C251.515 (5)
C14—H140.9800C24—H240.9800
C15—O151.426 (3)C25—O251.432 (4)
C15—C161.511 (4)C25—C261.509 (4)
C15—H150.9800C25—H250.9800
O15—C111.428 (3)O25—C211.432 (3)
C11—O111.377 (3)C21—O211.372 (3)
C11—C121.517 (4)C21—C221.511 (4)
C11—H110.9800C21—H210.9800
C12—O121.432 (3)C22—O221.439 (3)
C12—H120.9800C22—H220.9800
O14—C14A1.327 (5)O21—C21A1.432 (6)
C14A—O14B1.173 (5)C21A—H21A0.9600
C14A—C14C1.474 (5)C21A—H21B0.9600
C14C—H14A0.9600C21A—H21C0.9600
C14C—H14B0.9600O22—C22A1.342 (4)
C14C—H14C0.9600C22A—O22B1.184 (5)
C16—O161.432 (5)C22A—C22C1.473 (5)
C16—H16A0.9700C22C—H22A0.9600
C16—H16B0.9700C22C—H22B0.9600
O16—C16A1.269 (6)C22C—H22C0.9600
C16A—O16B1.163 (5)O24—C24A1.313 (5)
C16A—C16C1.478 (8)C24A—O24B1.151 (5)
C16C—H16C0.9600C24A—C24C1.470 (6)
C16C—H16D0.9600C24C—H24A0.9600
C16C—H16E0.9600C24C—H24B0.9600
O11—C11A1.425 (6)C24C—H24C0.9600
C11A—H11A0.9600C26—O261.428 (5)
C11A—H11B0.9600C26—H26A0.9700
C11A—H11C0.9600C26—H26B0.9700
O12—C12A1.327 (4)O26—C26A1.340 (4)
C12A—O12B1.190 (5)C26A—O26B1.181 (4)
C12A—C12C1.488 (5)C26A—C26C1.474 (7)
C12C—H12A0.9600C26C—H26C0.9600
C12C—H12B0.9600C26C—H26D0.9600
C12C—H12C0.9600C26C—H26E0.9600
C13i—S1—C13102.64 (18)C23—S2—C23ii103.03 (19)
C12—C13—C14106.2 (2)C24—C23—C22107.0 (2)
C12—C13—S1109.04 (19)C24—C23—S2113.33 (19)
C14—C13—S1113.80 (18)C22—C23—S2109.5 (2)
C12—C13—H13109.2C24—C23—H23109.0
C14—C13—H13109.2C22—C23—H23109.0
S1—C13—H13109.2S2—C23—H23109.0
O14—C14—C15109.3 (2)O24—C24—C25110.0 (2)
O14—C14—C13111.6 (2)O24—C24—C23110.1 (2)
C15—C14—C13111.6 (2)C25—C24—C23110.5 (2)
O14—C14—H14108.1O24—C24—H24108.7
C15—C14—H14108.1C25—C24—H24108.7
C13—C14—H14108.1C23—C24—H24108.7
O15—C15—C14108.7 (2)O25—C25—C26106.8 (2)
O15—C15—C16106.7 (2)O25—C25—C24107.1 (2)
C14—C15—C16113.4 (3)C26—C25—C24113.2 (3)
O15—C15—H15109.3O25—C25—H25109.9
C14—C15—H15109.3C26—C25—H25109.9
C16—C15—H15109.3C24—C25—H25109.9
C15—O15—C11114.94 (19)C25—O25—C21115.02 (19)
O11—C11—O15107.9 (2)O21—C21—O25107.3 (2)
O11—C11—C12108.7 (2)O21—C21—C22108.1 (2)
O15—C11—C12108.0 (2)O25—C21—C22108.0 (3)
O11—C11—H11110.7O21—C21—H21111.1
O15—C11—H11110.7O25—C21—H21111.1
C12—C11—H11110.7C22—C21—H21111.1
O12—C12—C11107.5 (2)O22—C22—C21107.4 (2)
O12—C12—C13111.4 (2)O22—C22—C23111.6 (2)
C11—C12—C13111.5 (2)C21—C22—C23111.3 (2)
O12—C12—H12108.8O22—C22—H22108.8
C11—C12—H12108.8C21—C22—H22108.8
C13—C12—H12108.8C23—C22—H22108.8
C14A—O14—C14117.8 (2)C21—O21—C21A113.5 (3)
O14B—C14A—O14121.7 (3)O21—C21A—H21A109.5
O14B—C14A—C14C124.7 (4)O21—C21A—H21B109.5
O14—C14A—C14C113.6 (3)H21A—C21A—H21B109.5
C14A—C14C—H14A109.5O21—C21A—H21C109.5
C14A—C14C—H14B109.5H21A—C21A—H21C109.5
H14A—C14C—H14B109.5H21B—C21A—H21C109.5
C14A—C14C—H14C109.5C22A—O22—C22117.4 (3)
H14A—C14C—H14C109.5O22B—C22A—O22121.8 (3)
H14B—C14C—H14C109.5O22B—C22A—C22C126.1 (3)
O16—C16—C15109.1 (3)O22—C22A—C22C112.0 (3)
O16—C16—H16A109.9C22A—C22C—H22A109.5
C15—C16—H16A109.9C22A—C22C—H22B109.5
O16—C16—H16B109.9H22A—C22C—H22B109.5
C15—C16—H16B109.9C22A—C22C—H22C109.5
H16A—C16—H16B108.3H22A—C22C—H22C109.5
C16A—O16—C16121.0 (3)H22B—C22C—H22C109.5
O16B—C16A—O16119.3 (6)C24A—O24—C24119.1 (3)
O16B—C16A—C16C125.4 (5)O24B—C24A—O24119.5 (4)
O16—C16A—C16C115.3 (4)O24B—C24A—C24C124.4 (4)
C16A—C16C—H16C109.5O24—C24A—C24C116.1 (3)
C16A—C16C—H16D109.5C24A—C24C—H24A109.5
H16C—C16C—H16D109.5C24A—C24C—H24B109.5
C16A—C16C—H16E109.5H24A—C24C—H24B109.5
H16C—C16C—H16E109.5C24A—C24C—H24C109.5
H16D—C16C—H16E109.5H24A—C24C—H24C109.5
C11—O11—C11A114.5 (3)H24B—C24C—H24C109.5
O11—C11A—H11A109.5O26—C26—C25111.8 (3)
O11—C11A—H11B109.5O26—C26—H26A109.2
H11A—C11A—H11B109.5C25—C26—H26A109.2
O11—C11A—H11C109.5O26—C26—H26B109.2
H11A—C11A—H11C109.5C25—C26—H26B109.2
H11B—C11A—H11C109.5H26A—C26—H26B107.9
C12A—O12—C12116.9 (3)C26A—O26—C26116.0 (3)
O12B—C12A—O12123.2 (3)O26B—C26A—O26123.4 (4)
O12B—C12A—C12C125.8 (4)O26B—C26A—C26C125.3 (4)
O12—C12A—C12C110.9 (4)O26—C26A—C26C111.3 (3)
C12A—C12C—H12A109.5C26A—C26C—H26C109.5
C12A—C12C—H12B109.5C26A—C26C—H26D109.5
H12A—C12C—H12B109.5H26C—C26C—H26D109.5
C12A—C12C—H12C109.5C26A—C26C—H26E109.5
H12A—C12C—H12C109.5H26C—C26C—H26E109.5
H12B—C12C—H12C109.5H26D—C26C—H26E109.5
C13i—S1—C13—C12147.8 (2)C23ii—S2—C23—C22151.4 (2)
C13i—S1—C13—C1493.8 (2)C23ii—S2—C23—C2489.2 (2)
C12—C13—C14—O14179.1 (2)C22—C23—C24—O24179.8 (2)
S1—C13—C14—O1459.1 (3)S2—C23—C24—O2459.0 (3)
C12—C13—C14—C1556.5 (3)C22—C23—C24—C2558.1 (3)
S1—C13—C14—C1563.5 (3)S2—C23—C24—C2562.8 (3)
O14—C14—C15—O15178.6 (2)O24—C24—C25—O25178.4 (2)
C13—C14—C15—O1557.6 (3)C23—C24—C25—O2559.8 (3)
O14—C14—C15—C1660.0 (3)O24—C24—C25—C2660.9 (3)
C13—C14—C15—C16176.1 (2)C23—C24—C25—C26177.2 (2)
C14—C15—O15—C1160.2 (3)C26—C25—O25—C21175.8 (3)
C16—C15—O15—C11177.1 (3)C24—C25—O25—C2162.6 (3)
C15—O15—C11—O11177.7 (3)C25—O25—C21—O21177.5 (3)
C15—O15—C11—C1260.4 (3)C25—O25—C21—C2261.2 (3)
O11—C11—C12—O1262.6 (3)O21—C21—C22—O2264.9 (3)
O15—C11—C12—O12179.32 (19)O25—C21—C22—O22179.29 (18)
O11—C11—C12—C13175.1 (2)O21—C21—C22—C23172.7 (2)
O15—C11—C12—C1358.4 (3)O25—C21—C22—C2356.8 (3)
C14—C13—C12—O12177.0 (2)C24—C23—C22—O22176.6 (2)
S1—C13—C12—O1254.0 (3)S2—C23—C22—O2253.4 (3)
C14—C13—C12—C1156.9 (3)C24—C23—C22—C2156.6 (3)
S1—C13—C12—C1166.1 (3)S2—C23—C22—C2166.6 (3)
C15—C14—O14—C14A136.4 (3)O25—C21—O21—C21A74.9 (4)
C13—C14—O14—C14A99.7 (3)C22—C21—O21—C21A168.8 (3)
C14—O14—C14A—O14B4.3 (7)C21—C22—O22—C22A145.7 (2)
C14—O14—C14A—C14C175.5 (4)C23—C22—O22—C22A92.1 (3)
O15—C15—C16—O1662.7 (4)C22—O22—C22A—O22B2.1 (5)
C14—C15—C16—O1657.0 (4)C22—O22—C22A—C22C178.7 (2)
C15—C16—O16—C16A132.0 (4)C25—C24—O24—C24A134.0 (4)
C16—O16—C16A—O16B7.2 (9)C23—C24—O24—C24A104.0 (4)
C16—O16—C16A—C16C175.8 (4)C24—O24—C24A—O24B2.7 (8)
O15—C11—O11—C11A78.7 (4)C24—O24—C24A—C24C177.2 (3)
C12—C11—O11—C11A164.4 (3)O25—C25—C26—O2669.2 (3)
C11—C12—O12—C12A146.0 (3)C24—C25—C26—O26173.2 (3)
C13—C12—O12—C12A91.5 (3)C25—C26—O26—C26A89.9 (3)
C12—O12—C12A—O12B0.7 (5)C26—O26—C26A—O26B2.0 (5)
C12—O12—C12A—C12C175.7 (3)C26—O26—C26A—C26C178.1 (4)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC26H38O16S
Mr638.62
Crystal system, space groupMonoclinic, C2
Temperature (K)293
a, b, c (Å)22.6458 (13), 7.2018 (3), 21.3260 (12)
β (°) 109.258 (7)
V3)3283.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.30 × 0.05 × 0.05
Data collection
DiffractometerOxford Diffraction Xcalibur-II with Sapphire-III CCD
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.95, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
10820, 4492, 3486
Rint0.021
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.110, 1.05
No. of reflections4492
No. of parameters398
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.27
Absolute structureFlack (1983), 1101 Friedel pairs
Absolute structure parameter0.03 (9)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996), PLATON (Spek, 2003).

 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds