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The absolute chemical configuration of the title compound, C13H22O8S, was determined unambiguously by X-ray diffraction for the first time.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013455/hg6051sup1.cif
Contains datablocks II, paper

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013455/hg6051IIsup2.hkl
Contains datablock II

CCDC reference: 248801

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.090
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.50 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.25 From the CIF: _reflns_number_total 2686 Count of symmetry unique reflns 1679 Completeness (_total/calc) 159.98% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1007 Fraction of Friedel pairs measured 0.600 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: IPDS (Stoe & Cie, 1997); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.

1.2.5.6-Di-O-isopropylidene-3-O-methylsulfonyl-α-D-glucofuranose top
Crystal data top
C13H22O8SDx = 1.408 Mg m3
Mr = 338.37Melting point: 355(1) K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 8.866 (3) ÅCell parameters from 5000 reflections
b = 9.2962 (16) Åθ = 2.5–25.0°
c = 19.361 (3) ŵ = 0.24 mm1
V = 1595.8 (7) Å3T = 150 K
Z = 4Block, white
F(000) = 7200.48 × 0.40 × 0.20 mm
Data collection top
Stoe IPDS
diffractometer
2236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.086
Planar graphite monochromatorθmax = 25.3°, θmin = 2.5°
Detector resolution: 6.667 pixels mm-1h = 1010
φ scansk = 118
6444 measured reflectionsl = 1923
2686 independent 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) + (0.0459P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090(Δ/σ)max = 0.005
S = 0.93Δρmax = 0.23 e Å3
2686 reflectionsΔρmin = 0.43 e Å3
209 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.010 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (10)
Special details top

Experimental. Recrystallized from methylcyclohexane. During data collection the crystal was in cold N2 gas of the Cryostream Cooler (Oxford Cryosystems) mounted on a φ-axis diffractometer supplied with an area detector.

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
C10.3896 (3)0.1403 (3)0.23268 (14)0.0162 (6)
H10.32430.22790.23030.019*
C20.5182 (3)0.1668 (3)0.28368 (14)0.0172 (6)
H20.56280.26510.27890.026 (9)*
C30.4396 (3)0.1454 (4)0.35284 (15)0.0177 (6)
H30.50820.10690.38940.010 (7)*
C40.2208 (3)0.2415 (3)0.39829 (15)0.0193 (6)
C50.3071 (3)0.0434 (3)0.33604 (14)0.0186 (6)
H50.31780.05050.36070.011 (7)*
C60.4290 (3)0.0925 (4)0.16034 (14)0.0196 (7)
H60.49340.00420.16160.015 (7)*
C70.2869 (3)0.0664 (4)0.11592 (14)0.0261 (7)
H7A0.27410.03740.10600.031*
H7B0.19550.10210.13980.031*
C80.4667 (3)0.1935 (4)0.05373 (15)0.0205 (7)
C90.5659 (3)0.0832 (4)0.01820 (17)0.0294 (7)
H9A0.67060.11720.01800.035*
H9B0.53140.06960.02940.035*
H9C0.56000.00840.04310.035*
C100.4739 (3)0.3396 (4)0.02064 (17)0.0263 (7)
H10A0.40700.40580.04540.032*
H10B0.44180.33250.02770.032*
H10C0.57770.37580.02260.032*
C110.8813 (3)0.1886 (4)0.24291 (18)0.0283 (7)
H11A0.86930.14800.19650.034*
H11B0.98890.19790.25360.034*
H11C0.83360.28370.24470.034*
C120.1165 (3)0.3639 (4)0.38226 (18)0.0286 (7)
H12A0.11780.38280.33250.034*
H12B0.14980.45000.40710.034*
H12C0.01390.33880.39670.034*
C130.2290 (3)0.2040 (4)0.47382 (17)0.0288 (7)
H13A0.13000.17080.48970.035*
H13B0.25890.28920.50030.035*
H13C0.30360.12750.48070.035*
O10.36905 (19)0.2773 (2)0.37190 (11)0.0197 (5)
O20.17704 (19)0.1184 (2)0.35810 (11)0.0231 (5)
O30.3061 (2)0.0241 (2)0.26381 (10)0.0208 (5)
O40.31308 (19)0.1447 (3)0.05423 (10)0.0258 (5)
O50.50549 (19)0.2067 (2)0.12545 (10)0.0210 (5)
O60.62951 (18)0.0529 (2)0.27332 (10)0.0193 (5)
O70.8601 (2)0.0646 (3)0.29966 (12)0.0293 (5)
O80.7867 (2)0.1481 (3)0.36831 (11)0.0278 (5)
S0.79571 (7)0.07493 (8)0.30346 (4)0.01918 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0147 (12)0.0147 (14)0.0192 (15)0.0019 (10)0.0014 (10)0.0020 (13)
C20.0145 (11)0.0161 (16)0.0212 (15)0.0015 (10)0.0009 (10)0.0035 (13)
C30.0184 (12)0.0185 (16)0.0162 (15)0.0011 (12)0.0036 (10)0.0000 (14)
C40.0136 (12)0.0227 (16)0.0217 (15)0.0045 (12)0.0056 (11)0.0005 (13)
C50.0213 (12)0.0178 (16)0.0168 (14)0.0013 (13)0.0028 (11)0.0007 (12)
C60.0178 (12)0.0237 (17)0.0175 (15)0.0035 (11)0.0015 (10)0.0037 (14)
C70.0230 (13)0.0385 (18)0.0168 (14)0.0135 (15)0.0032 (11)0.0021 (15)
C80.0127 (12)0.0281 (18)0.0208 (16)0.0036 (11)0.0005 (10)0.0012 (14)
C90.0282 (14)0.0322 (19)0.0276 (18)0.0021 (14)0.0060 (12)0.0011 (18)
C100.0244 (13)0.0270 (18)0.0276 (17)0.0015 (13)0.0015 (12)0.0030 (15)
C110.0235 (14)0.0283 (19)0.0331 (19)0.0012 (13)0.0045 (12)0.0009 (16)
C120.0253 (13)0.0296 (18)0.0310 (18)0.0048 (14)0.0002 (13)0.0062 (16)
C130.0296 (15)0.0322 (19)0.0246 (17)0.0052 (13)0.0071 (12)0.0017 (16)
O10.0174 (8)0.0205 (11)0.0211 (11)0.0043 (8)0.0067 (8)0.0031 (10)
O20.0172 (9)0.0260 (12)0.0260 (11)0.0046 (8)0.0036 (8)0.0092 (10)
O30.0204 (9)0.0234 (11)0.0186 (11)0.0068 (9)0.0012 (8)0.0035 (9)
O40.0143 (8)0.0364 (13)0.0266 (12)0.0054 (9)0.0054 (8)0.0053 (10)
O50.0180 (9)0.0283 (12)0.0166 (10)0.0064 (8)0.0014 (7)0.0023 (10)
O60.0125 (8)0.0221 (11)0.0234 (10)0.0001 (8)0.0026 (7)0.0059 (10)
O70.0212 (8)0.0285 (12)0.0380 (13)0.0034 (9)0.0032 (9)0.0009 (13)
O80.0192 (8)0.0398 (13)0.0243 (11)0.0009 (10)0.0032 (8)0.0086 (11)
S0.0141 (3)0.0223 (4)0.0211 (4)0.0011 (3)0.0019 (3)0.0020 (3)
Geometric parameters (Å, º) top
C1—O31.442 (3)C8—O51.436 (4)
C1—C61.510 (4)C8—O41.436 (3)
C1—C21.528 (4)C8—C101.503 (5)
C1—H11.0000C8—C91.516 (4)
C2—O61.462 (3)C9—H9A0.9800
C2—C31.522 (4)C9—H9B0.9800
C2—H21.0000C9—H9C0.9800
C3—O11.425 (4)C10—H10A0.9800
C3—C51.544 (4)C10—H10B0.9800
C3—H31.0000C10—H10C0.9800
C4—O21.437 (4)C11—S1.752 (3)
C4—O11.449 (3)C11—H11A0.9800
C4—C121.498 (4)C11—H11B0.9800
C4—C131.505 (4)C11—H11C0.9800
C5—O31.410 (3)C12—H12A0.9800
C5—O21.414 (3)C12—H12B0.9800
C5—H51.0000C12—H12C0.9800
C6—O51.429 (4)C13—H13A0.9800
C6—C71.545 (3)C13—H13B0.9800
C6—H61.0000C13—H13C0.9800
C7—O41.418 (4)O6—S1.5982 (17)
C7—H7A0.9900O7—S1.419 (2)
C7—H7B0.9900O8—S1.430 (2)
O3—C1—C6106.6 (2)O5—C8—C9110.9 (2)
O3—C1—C2103.5 (2)O4—C8—C9109.9 (3)
C6—C1—C2118.3 (2)C10—C8—C9113.1 (3)
O3—C1—H1109.3C8—C9—H9A109.5
C6—C1—H1109.3C8—C9—H9B109.5
C2—C1—H1109.3H9A—C9—H9B109.5
O6—C2—C3109.6 (2)C8—C9—H9C109.5
O6—C2—C1107.4 (2)H9A—C9—H9C109.5
C3—C2—C1101.9 (2)H9B—C9—H9C109.5
O6—C2—H2112.5C8—C10—H10A109.5
C3—C2—H2112.5C8—C10—H10B109.5
C1—C2—H2112.5H10A—C10—H10B109.5
O1—C3—C2108.4 (2)C8—C10—H10C109.5
O1—C3—C5104.4 (2)H10A—C10—H10C109.5
C2—C3—C5104.1 (2)H10B—C10—H10C109.5
O1—C3—H3113.1S—C11—H11A109.5
C2—C3—H3113.1S—C11—H11B109.5
C5—C3—H3113.1H11A—C11—H11B109.5
O2—C4—O1103.7 (2)S—C11—H11C109.5
O2—C4—C12109.0 (2)H11A—C11—H11C109.5
O1—C4—C12108.2 (2)H11B—C11—H11C109.5
O2—C4—C13110.8 (3)C4—C12—H12A109.5
O1—C4—C13110.6 (2)C4—C12—H12B109.5
C12—C4—C13114.0 (3)H12A—C12—H12B109.5
O3—C5—O2110.9 (2)C4—C12—H12C109.5
O3—C5—C3107.0 (2)H12A—C12—H12C109.5
O2—C5—C3104.7 (2)H12B—C12—H12C109.5
O3—C5—H5111.3C4—C13—H13A109.5
O2—C5—H5111.3C4—C13—H13B109.5
C3—C5—H5111.3H13A—C13—H13B109.5
O5—C6—C1109.2 (2)C4—C13—H13C109.5
O5—C6—C7103.9 (2)H13A—C13—H13C109.5
C1—C6—C7112.0 (2)H13B—C13—H13C109.5
O5—C6—H6110.5C3—O1—C4107.0 (2)
C1—C6—H6110.5C5—O2—C4109.64 (19)
C7—C6—H6110.5C5—O3—C1108.4 (2)
O4—C7—C6104.8 (2)C7—O4—C8108.9 (2)
O4—C7—H7A110.8C6—O5—C8106.3 (2)
C6—C7—H7A110.8C2—O6—S118.66 (17)
O4—C7—H7B110.8O7—S—O8120.19 (14)
C6—C7—H7B110.8O7—S—O6103.55 (12)
H7A—C7—H7B108.9O8—S—O6109.27 (11)
O5—C8—O4104.3 (2)O7—S—C11110.05 (15)
O5—C8—C10109.0 (3)O8—S—C11108.94 (16)
O4—C8—C10109.2 (2)O6—S—C11103.46 (13)
O3—C1—C2—O677.0 (2)O3—C5—O2—C4126.2 (2)
C6—C1—C2—O640.6 (3)C3—C5—O2—C411.2 (3)
O3—C1—C2—C338.1 (3)O1—C4—O2—C527.3 (3)
C6—C1—C2—C3155.7 (3)C12—C4—O2—C5142.4 (2)
O6—C2—C3—O1161.88 (19)C13—C4—O2—C591.3 (3)
C1—C2—C3—O184.6 (3)O2—C5—O3—C194.1 (2)
O6—C2—C3—C587.4 (2)C3—C5—O3—C119.6 (3)
C1—C2—C3—C526.1 (3)C6—C1—O3—C5162.1 (2)
O1—C3—C5—O3108.3 (2)C2—C1—O3—C536.6 (3)
C2—C3—C5—O35.3 (3)C6—C7—O4—C89.6 (3)
O1—C3—C5—O29.5 (3)O5—C8—O4—C727.7 (3)
C2—C3—C5—O2123.1 (2)C10—C8—O4—C7144.1 (3)
O3—C1—C6—O5177.01 (19)C9—C8—O4—C791.3 (3)
C2—C1—C6—O567.0 (3)C1—C6—O5—C8148.7 (2)
O3—C1—C6—C762.5 (3)C7—C6—O5—C829.0 (3)
C2—C1—C6—C7178.4 (3)O4—C8—O5—C635.5 (3)
O5—C6—C7—O411.9 (3)C10—C8—O5—C6152.0 (2)
C1—C6—C7—O4129.7 (3)C9—C8—O5—C682.8 (3)
C2—C3—O1—C4136.9 (2)C3—C2—O6—S87.0 (2)
C5—C3—O1—C426.4 (3)C1—C2—O6—S163.10 (17)
O2—C4—O1—C333.4 (3)C2—O6—S—O7166.3 (2)
C12—C4—O1—C3149.1 (2)C2—O6—S—O837.0 (2)
C13—C4—O1—C385.4 (3)C2—O6—S—C1178.9 (2)
 

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