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In the title compound, C14H30O4Si, the bond angles around Si are in the range 105.4 (3)–112.1 (4)° and the tetra­hydro­furan ring adopts a distorted envelope conformation. There is one intra­molecular and one inter­molecular O—H...O hydrogen bond in the crystal structure. A spiral of mol­ecules forms around the 41 axis (c axis) of the crystal structure via the inter­molecular O—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016831/sj6091sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016831/sj6091Isup2.hkl
Contains datablock I

CCDC reference: 277781

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.067
  • wR factor = 0.182
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 12
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 25.36 From the CIF: _reflns_number_total 1607 From the CIF: _diffrn_reflns_limit_ max hkl 14. 10. 13. From the CIF: _diffrn_reflns_limit_ min hkl -14. -10. -13. TEST1: Expected hkl limits for theta max Calculated maximum hkl 14. 14. 13. Calculated minimum hkl -14. -14. -13. 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 25.36 From the CIF: _reflns_number_total 1607 Count of symmetry unique reflns 1639 Completeness (_total/calc) 98.05% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).

(2S,3R,4R,5R)-2-(tert-Butyldimethylsilyloxymethyl)-2,4,5- trimethyltetrahydrofuran-3,4-diol top
Crystal data top
C14H30O4SiDx = 1.130 Mg m3
Mr = 290.47Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41Cell parameters from 20589 reflections
Hall symbol: P 4wθ = 3.0–25.4°
a = 12.3616 (12) ŵ = 0.15 mm1
c = 11.1685 (11) ÅT = 173 K
V = 1706.6 (3) Å3Needle, colourless
Z = 40.36 × 0.08 × 0.08 mm
F(000) = 640
Data collection top
Nonius KappaCCD
diffractometer
1227 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 25.4°, θmin = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 1414
ω scansk = 1010
20589 measured reflectionsl = 1313
1607 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0495P)2 + 4.0462P]
where P = (Fo2 + 2Fc2)/3
1607 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.26 e Å3
Special details top

Experimental. 221 frames via ω-rotation (Δω=2°) and two times 60 s per frame (five sets at different κ-angles)

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
Si0.80268 (19)0.21735 (18)0.0049 (2)0.0342 (5)
O10.7408 (4)0.1343 (4)0.3753 (5)0.0379 (14)
O20.7934 (5)0.3766 (4)0.4828 (6)0.0403 (14)
H20.77540.44040.48380.060*
O30.5930 (4)0.2760 (5)0.2654 (5)0.0382 (14)
H30.63790.24630.22250.057*
O40.7780 (4)0.2226 (5)0.1419 (5)0.0393 (15)
C10.8184 (7)0.2211 (7)0.3552 (8)0.038 (2)
C20.7553 (6)0.3271 (6)0.3747 (7)0.0301 (18)
H2B0.76480.37590.30640.036*
C30.6371 (7)0.2892 (6)0.3840 (7)0.0356 (19)
C40.6537 (7)0.1786 (7)0.4409 (9)0.043 (2)
H4A0.67680.18880.52400.052*
C50.9163 (6)0.2053 (7)0.4405 (9)0.041 (2)
H5A0.95400.14010.41930.062*
H5B0.89100.20000.52150.062*
H5C0.96440.26590.43340.062*
C60.5614 (7)0.3637 (7)0.4507 (8)0.043 (2)
H6A0.49010.33280.45200.065*
H6B0.55910.43260.41120.065*
H6C0.58680.37310.53130.065*
C70.5597 (7)0.1014 (8)0.4393 (9)0.051 (2)
H7A0.58450.03000.45890.076*
H7B0.52770.10080.36090.076*
H7C0.50680.12400.49700.076*
C80.8610 (7)0.2057 (7)0.2277 (8)0.040 (2)
H8A0.91950.25630.21320.048*
H8B0.88950.13300.21910.048*
C90.8615 (8)0.0826 (7)0.0397 (9)0.052 (3)
H9A0.92830.07380.00310.077*
H9B0.87500.07750.12420.077*
H9C0.81170.02700.01620.077*
C100.8998 (7)0.3231 (7)0.0482 (9)0.046 (2)
H10A0.97100.30260.02270.069*
H10B0.88000.39020.01080.069*
H10C0.89890.33170.13360.069*
C110.6661 (7)0.2363 (8)0.0798 (8)0.041 (2)
C120.5898 (7)0.1440 (8)0.0436 (9)0.058 (3)
H12A0.52170.15260.08370.086*
H12B0.57870.14570.04150.086*
H12C0.62150.07590.06580.086*
C130.6200 (7)0.3467 (8)0.0455 (8)0.052 (2)
H13A0.55000.35560.08140.078*
H13B0.66760.40260.07350.078*
H13C0.61350.35130.04000.078*
C140.6838 (8)0.2326 (8)0.2153 (8)0.047 (2)
H14A0.61520.22690.25510.070*
H14B0.72770.17120.23520.070*
H14C0.71970.29760.24060.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si0.0373 (13)0.0351 (13)0.0301 (11)0.0008 (11)0.0017 (11)0.0029 (11)
O10.044 (3)0.026 (3)0.043 (3)0.003 (3)0.004 (3)0.001 (3)
O20.044 (3)0.035 (3)0.042 (3)0.005 (3)0.003 (3)0.013 (3)
O30.033 (3)0.045 (3)0.037 (3)0.003 (3)0.001 (3)0.004 (3)
O40.031 (3)0.054 (4)0.033 (3)0.001 (3)0.004 (3)0.001 (3)
C10.033 (5)0.043 (5)0.039 (5)0.004 (4)0.005 (4)0.008 (4)
C20.030 (4)0.032 (4)0.028 (4)0.002 (4)0.008 (4)0.007 (4)
C30.046 (5)0.036 (5)0.024 (4)0.001 (4)0.000 (4)0.002 (4)
C40.040 (5)0.047 (5)0.042 (5)0.004 (4)0.008 (4)0.003 (4)
C50.029 (4)0.046 (5)0.050 (6)0.003 (4)0.002 (4)0.005 (5)
C60.041 (5)0.041 (5)0.048 (6)0.001 (4)0.006 (4)0.009 (4)
C70.038 (5)0.058 (6)0.055 (6)0.015 (4)0.010 (5)0.001 (5)
C80.032 (4)0.051 (5)0.037 (5)0.004 (4)0.001 (4)0.002 (4)
C90.056 (6)0.041 (5)0.058 (7)0.013 (4)0.011 (5)0.004 (5)
C100.044 (5)0.046 (5)0.048 (6)0.002 (4)0.003 (5)0.007 (4)
C110.040 (5)0.052 (5)0.031 (5)0.004 (4)0.002 (4)0.000 (4)
C120.039 (5)0.082 (7)0.052 (7)0.015 (5)0.003 (5)0.007 (6)
C130.049 (6)0.071 (7)0.035 (6)0.010 (5)0.002 (4)0.002 (5)
C140.057 (6)0.051 (6)0.033 (5)0.001 (5)0.004 (4)0.006 (4)
Geometric parameters (Å, º) top
Si—O41.669 (6)C6—H6C0.9600
Si—C101.839 (9)C7—H7A0.9600
Si—C91.859 (8)C7—H7B0.9600
Si—C111.899 (9)C7—H7C0.9600
O1—C41.413 (10)C8—H8A0.9700
O1—C11.457 (10)C8—H8B0.9700
O2—C21.433 (10)C9—H9A0.9600
O2—H20.8200C9—H9B0.9600
O3—C31.442 (10)C9—H9C0.9600
O3—H30.8200C10—H10A0.9600
O4—C81.419 (10)C10—H10B0.9600
C1—C81.530 (13)C10—H10C0.9600
C1—C21.540 (11)C11—C131.528 (13)
C1—C51.552 (12)C11—C141.530 (12)
C2—C31.539 (11)C11—C121.534 (12)
C2—H2B0.9800C12—H12A0.9600
C3—C61.509 (11)C12—H12B0.9600
C3—C41.521 (11)C12—H12C0.9600
C4—C71.504 (12)C13—H13A0.9600
C4—H4A0.9800C13—H13B0.9600
C5—H5A0.9600C13—H13C0.9600
C5—H5B0.9600C14—H14A0.9600
C5—H5C0.9600C14—H14B0.9600
C6—H6A0.9600C14—H14C0.9600
C6—H6B0.9600
O4—Si—C10110.5 (4)C4—C7—H7B109.5
O4—Si—C9108.2 (4)H7A—C7—H7B109.5
C10—Si—C9109.0 (4)C4—C7—H7C109.5
O4—Si—C11105.4 (3)H7A—C7—H7C109.5
C10—Si—C11112.1 (4)H7B—C7—H7C109.5
C9—Si—C11111.5 (4)O4—C8—C1111.2 (6)
C4—O1—C1107.3 (6)O4—C8—H8A109.4
C2—O2—H2109.5C1—C8—H8A109.4
C3—O3—H3109.5O4—C8—H8B109.4
C8—O4—Si121.7 (5)C1—C8—H8B109.4
O1—C1—C8106.2 (7)H8A—C8—H8B108.0
O1—C1—C2105.7 (6)Si—C9—H9A109.5
C8—C1—C2114.3 (7)Si—C9—H9B109.5
O1—C1—C5109.0 (7)H9A—C9—H9B109.5
C8—C1—C5106.7 (7)Si—C9—H9C109.5
C2—C1—C5114.5 (7)H9A—C9—H9C109.5
O2—C2—C3112.6 (7)H9B—C9—H9C109.5
O2—C2—C1108.4 (6)Si—C10—H10A109.5
C3—C2—C1103.4 (6)Si—C10—H10B109.5
O2—C2—H2B110.7H10A—C10—H10B109.5
C3—C2—H2B110.7Si—C10—H10C109.5
C1—C2—H2B110.7H10A—C10—H10C109.5
O3—C3—C6106.8 (7)H10B—C10—H10C109.5
O3—C3—C4109.4 (7)C13—C11—C14109.1 (8)
C6—C3—C4115.2 (7)C13—C11—C12111.7 (8)
O3—C3—C2109.3 (6)C14—C11—C12109.1 (8)
C6—C3—C2115.9 (7)C13—C11—Si109.3 (6)
C4—C3—C2100.0 (7)C14—C11—Si107.8 (6)
O1—C4—C7109.7 (7)C12—C11—Si109.8 (6)
O1—C4—C3103.6 (7)C11—C12—H12A109.5
C7—C4—C3117.5 (8)C11—C12—H12B109.5
O1—C4—H4A108.6H12A—C12—H12B109.5
C7—C4—H4A108.6C11—C12—H12C109.5
C3—C4—H4A108.6H12A—C12—H12C109.5
C1—C5—H5A109.5H12B—C12—H12C109.5
C1—C5—H5B109.5C11—C13—H13A109.5
H5A—C5—H5B109.5C11—C13—H13B109.5
C1—C5—H5C109.5H13A—C13—H13B109.5
H5A—C5—H5C109.5C11—C13—H13C109.5
H5B—C5—H5C109.5H13A—C13—H13C109.5
C3—C6—H6A109.5H13B—C13—H13C109.5
C3—C6—H6B109.5C11—C14—H14A109.5
H6A—C6—H6B109.5C11—C14—H14B109.5
C3—C6—H6C109.5H14A—C14—H14B109.5
H6A—C6—H6C109.5C11—C14—H14C109.5
H6B—C6—H6C109.5H14A—C14—H14C109.5
C4—C7—H7A109.5H14B—C14—H14C109.5
C10—Si—O4—C862.0 (7)O3—C3—C4—O170.2 (8)
C9—Si—O4—C857.3 (7)C6—C3—C4—O1169.5 (7)
C11—Si—O4—C8176.6 (6)C2—C3—C4—O144.5 (7)
C4—O1—C1—C8140.7 (7)O3—C3—C4—C750.9 (10)
C4—O1—C1—C218.9 (8)C6—C3—C4—C769.4 (10)
C4—O1—C1—C5104.6 (8)C2—C3—C4—C7165.6 (8)
O1—C1—C2—O2110.2 (7)Si—O4—C8—C1176.8 (6)
C8—C1—C2—O2133.4 (7)O1—C1—C8—O466.0 (8)
C5—C1—C2—O29.8 (9)C2—C1—C8—O450.2 (9)
O1—C1—C2—C39.6 (8)C5—C1—C8—O4177.9 (7)
C8—C1—C2—C3106.8 (8)O4—Si—C11—C1361.3 (7)
C5—C1—C2—C3129.6 (7)C10—Si—C11—C1359.0 (7)
O2—C2—C3—O3160.2 (6)C9—Si—C11—C13178.5 (6)
C1—C2—C3—O383.0 (7)O4—Si—C11—C14179.8 (6)
O2—C2—C3—C639.5 (10)C10—Si—C11—C1459.5 (8)
C1—C2—C3—C6156.3 (7)C9—Si—C11—C1463.1 (8)
O2—C2—C3—C485.0 (7)O4—Si—C11—C1261.5 (7)
C1—C2—C3—C431.8 (8)C10—Si—C11—C12178.2 (7)
C1—O1—C4—C7166.6 (7)C9—Si—C11—C1255.6 (7)
C1—O1—C4—C340.3 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.822.022.834 (7)170
O3—H3···O40.821.972.750 (8)158
Symmetry code: (i) y+1, x, z+1/4.
 

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