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In the crystalline state, the title compound, C9H16O5S, forms hydrogen-bonded chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049634/at2162sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049634/at2162Isup2.hkl
Contains datablock I

CCDC reference: 629418

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.052
  • wR factor = 0.130
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.33 Ratio
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT354_ALERT_3_C Short O-H Bond (0.82A) O5 - H5O ... 0.70 Ang. PLAT420_ALERT_2_C D-H Without Acceptor S1 - H1S ... ?
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 27.55 From the CIF: _reflns_number_total 2324 Count of symmetry unique reflns 1369 Completeness (_total/calc) 169.76% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 955 Fraction of Friedel pairs measured 0.698 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

1,2-O-Isopropylidene-6-thio-α-D-glucofuranose top
Crystal data top
C9H16O5SF(000) = 252
Mr = 236.28Dx = 1.452 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1135 reflections
a = 9.1655 (8) Åθ = 1.0–27.5°
b = 5.8452 (5) ŵ = 0.30 mm1
c = 10.5282 (9) ÅT = 100 K
β = 106.563 (4)°Poor quality needle, colourless
V = 540.58 (8) Å30.5 × 0.1 × 0.1 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
2020 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
Graphite monochromatorθmax = 27.6°, θmin = 2.6°
Detector resolution: 1242 (horizontal) x 1152 (vertical) pixels, CCD pixel size is 22.5 x 22.5 µm which gives at the imput a pixel of 110 x 110 µm (with 2 x 2 binning) pixels mm-1h = 1111
128 frames via φ rotation (rotation angle 2.0°) and 2*200 s per frame scansk = 77
3891 measured reflectionsl = 1313
2324 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0298P)2 + 1.2765P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.010
2324 reflectionsΔρmax = 0.40 e Å3
150 parametersΔρmin = 0.45 e Å3
1 restraintAbsolute structure: Flack (1983), 955 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (15)
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
S10.84545 (13)0.32232 (19)0.48802 (9)0.0282 (3)
O30.6188 (3)0.1600 (5)1.0033 (2)0.0193 (6)
O10.8451 (3)0.1534 (5)0.8378 (2)0.0203 (6)
O20.8766 (3)0.2299 (4)1.0650 (2)0.0173 (6)
O50.5637 (3)0.1627 (5)0.5813 (3)0.0206 (6)
O40.5725 (4)0.3961 (5)0.6778 (3)0.0213 (7)
C50.7066 (5)0.0447 (6)0.6358 (4)0.0156 (7)
H50.71150.08650.57930.019*
C30.5805 (5)0.2177 (6)0.7720 (3)0.0173 (8)
H30.48130.14540.76150.021*
C40.7039 (4)0.0423 (7)0.7719 (4)0.0166 (8)
H40.69110.08910.82550.020*
C70.7571 (4)0.1161 (6)1.1057 (4)0.0173 (8)
C10.8187 (5)0.3089 (7)0.9343 (3)0.0178 (8)
H10.85940.46080.92440.021*
C20.6456 (4)0.3191 (7)0.9097 (3)0.0165 (8)
H20.60770.47330.91870.020*
C80.7460 (5)0.2190 (7)1.2346 (4)0.0235 (9)
H8A0.73970.38251.22650.035*
H8B0.83470.17801.30490.035*
H8C0.65670.16161.25430.035*
C90.7878 (5)0.1397 (7)1.1160 (4)0.0210 (8)
H9A0.70150.21761.13010.032*
H9B0.87610.16971.18900.032*
H9C0.80520.19351.03540.032*
C60.8424 (5)0.1982 (7)0.6456 (4)0.0218 (9)
H6A0.84200.32080.70760.026*
H6B0.93480.11010.68100.026*
H5O0.576 (6)0.263 (9)0.620 (5)0.028 (15)*
H4O0.520 (5)0.357 (7)0.606 (4)0.012 (10)*
H1S0.721 (6)0.472 (10)0.468 (5)0.052 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0343 (6)0.0310 (6)0.0181 (4)0.0033 (5)0.0057 (4)0.0076 (5)
O30.0207 (14)0.0227 (14)0.0130 (11)0.0012 (13)0.0025 (10)0.0025 (12)
O10.0207 (14)0.0240 (15)0.0141 (11)0.0014 (13)0.0016 (10)0.0067 (12)
O20.0162 (14)0.0211 (15)0.0130 (11)0.0032 (11)0.0015 (10)0.0016 (10)
O50.0274 (17)0.0172 (15)0.0139 (13)0.0003 (13)0.0004 (12)0.0022 (12)
O40.0303 (17)0.0180 (14)0.0108 (13)0.0004 (12)0.0016 (13)0.0003 (11)
C50.0214 (19)0.0098 (15)0.0140 (16)0.0037 (15)0.0024 (15)0.0013 (13)
C30.021 (2)0.016 (2)0.0126 (16)0.0017 (15)0.0007 (14)0.0021 (14)
C40.015 (2)0.0207 (19)0.0114 (16)0.0040 (16)0.0004 (14)0.0020 (14)
C70.019 (2)0.019 (2)0.0138 (16)0.0036 (15)0.0028 (15)0.0010 (13)
C10.025 (2)0.0146 (18)0.0107 (16)0.0078 (16)0.0004 (15)0.0031 (13)
C20.021 (2)0.0150 (18)0.0119 (16)0.0074 (16)0.0027 (14)0.0003 (14)
C80.034 (2)0.022 (2)0.0159 (17)0.0025 (17)0.0086 (17)0.0015 (15)
C90.023 (2)0.018 (2)0.0225 (19)0.0023 (17)0.0064 (16)0.0004 (16)
C60.024 (2)0.026 (2)0.0118 (17)0.0013 (17)0.0012 (15)0.0071 (15)
Geometric parameters (Å, º) top
S1—C61.818 (4)C3—C41.527 (5)
S1—H1S1.41 (6)C3—H30.9800
O3—C21.426 (5)C4—H40.9800
O3—C71.434 (5)C7—C81.514 (5)
O1—C11.434 (4)C7—C91.520 (5)
O1—C41.437 (5)C1—C21.534 (5)
O2—C11.405 (4)C1—H10.9800
O2—C71.447 (4)C2—H20.9800
O5—C51.446 (5)C8—H8A0.9600
O5—H5O0.71 (5)C8—H8B0.9600
O4—C31.427 (4)C8—H8C0.9600
O4—H4O0.80 (4)C9—H9A0.9600
C5—C61.514 (6)C9—H9B0.9600
C5—C41.527 (5)C9—H9C0.9600
C5—H50.9800C6—H6A0.9700
C3—C21.522 (5)C6—H6B0.9700
C6—S1—H1S99 (2)O2—C1—O1113.2 (3)
C2—O3—C7110.3 (3)O2—C1—C2105.2 (3)
C1—O1—C4108.5 (3)O1—C1—C2106.3 (3)
C1—O2—C7109.6 (3)O2—C1—H1110.7
C5—O5—H5O101 (4)O1—C1—H1110.7
C3—O4—H4O110 (3)C2—C1—H1110.7
O5—C5—C6112.2 (3)O3—C2—C3107.8 (3)
O5—C5—C4106.1 (3)O3—C2—C1103.4 (3)
C6—C5—C4111.5 (3)C3—C2—C1104.6 (3)
O5—C5—H5109.0O3—C2—H2113.4
C6—C5—H5109.0C3—C2—H2113.4
C4—C5—H5109.0C1—C2—H2113.4
O4—C3—C2107.8 (3)C7—C8—H8A109.5
O4—C3—C4112.4 (3)C7—C8—H8B109.5
C2—C3—C4100.0 (3)H8A—C8—H8B109.5
O4—C3—H3112.0C7—C8—H8C109.5
C2—C3—H3112.0H8A—C8—H8C109.5
C4—C3—H3112.0H8B—C8—H8C109.5
O1—C4—C3105.2 (3)C7—C9—H9A109.5
O1—C4—C5110.5 (3)C7—C9—H9B109.5
C3—C4—C5115.8 (3)H9A—C9—H9B109.5
O1—C4—H4108.4C7—C9—H9C109.5
C3—C4—H4108.4H9A—C9—H9C109.5
C5—C4—H4108.4H9B—C9—H9C109.5
O3—C7—O2106.1 (3)C5—C6—S1113.6 (3)
O3—C7—C8109.4 (3)C5—C6—H6A108.8
O2—C7—C8109.4 (3)S1—C6—H6A108.8
O3—C7—C9109.6 (3)C5—C6—H6B108.8
O2—C7—C9109.4 (3)S1—C6—H6B108.8
C8—C7—C9112.7 (3)H6A—C6—H6B107.7
 

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