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The mol­ecules of the title compound, C15H20O4, link via a single intermolecular hydrogen bond to form chains running along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017007/na6098sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017007/na6098Isup2.hkl
Contains datablock I

CCDC reference: 177216

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.146
  • Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 2254 Count of symmetry unique reflns 1447 Completeness (_total/calc) 155.77% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 807 Fraction of Friedel pairs measured 0.558 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997), COLLECT and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).

2-Hydroxy-2-[5-(1-hydroxy-1-methyl-ethyl)-tetrahydro-furan-2-yl]-1-phenyl- ethanone top
Crystal data top
C15H20O4Dx = 1.258 Mg m3
Mr = 264.31Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4487 reflections
a = 7.5556 (3) Åθ = 3.2–25.0°
b = 8.0446 (3) ŵ = 0.09 mm1
c = 22.9549 (8) ÅT = 150 K
V = 1395.24 (9) Å3Block, colourless
Z = 40.25 × 0.10 × 0.08 mm
F(000) = 568
Data collection top
Nonius KappaCCD area-detector
diffractometer
2254 independent reflections
Radiation source: Nonius FR591 Rotating anode1917 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 9.091 pixels mm1 pixels mm-1θmax = 25.0°, θmin = 3.2°
φ and ω scans to fill the Ewald sphereh = 78
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
k = 97
Tmin = 0.978, Tmax = 0.993l = 2622
4487 measured 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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0959P)2]
where P = (Fo2 + 2Fc2)/3
2254 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.24 e Å3
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
C10.7265 (3)0.3088 (3)0.89577 (11)0.0364 (6)
C20.8244 (3)0.3590 (4)0.94465 (11)0.0435 (6)
H20.85370.47290.94970.052*
C30.8783 (4)0.2435 (4)0.98544 (13)0.0512 (8)
H30.94530.27851.01820.061*
C40.8357 (4)0.0782 (4)0.97901 (13)0.0488 (7)
H40.87140.00001.00770.059*
C50.7405 (4)0.0257 (4)0.93061 (12)0.0451 (7)
H50.71250.08870.92600.054*
C60.6867 (3)0.1399 (3)0.88922 (11)0.0390 (6)
H60.62230.10350.85610.047*
C70.6666 (3)0.4387 (3)0.85403 (11)0.0370 (6)
C80.5324 (3)0.3935 (3)0.80714 (10)0.0372 (6)
H80.56390.28310.79000.045*
C90.3489 (4)0.3819 (3)0.83639 (11)0.0376 (6)
H90.34220.27650.85940.045*
C100.1930 (4)0.3880 (3)0.79365 (13)0.0456 (7)
H10A0.22900.35020.75430.055*
H10B0.09310.31880.80740.055*
C110.1443 (4)0.5721 (4)0.79354 (13)0.0429 (7)
H11A0.21700.63470.76510.051*
H11B0.01760.58820.78410.051*
C120.1844 (3)0.6261 (3)0.85529 (12)0.0382 (6)
H120.07780.60480.88000.046*
C130.2429 (4)0.8045 (3)0.86423 (11)0.0393 (6)
C140.1094 (4)0.9239 (4)0.83689 (14)0.0512 (8)
H14A0.14861.03870.84300.077*
H14B0.00670.90790.85510.077*
H14C0.10060.90180.79500.077*
C150.2691 (5)0.8429 (4)0.92893 (12)0.0528 (7)
H15A0.30690.95870.93350.079*
H15B0.35970.76890.94500.079*
H15C0.15730.82580.94970.079*
O10.7172 (2)0.5827 (3)0.85810 (9)0.0489 (5)
O20.5341 (3)0.5156 (2)0.76291 (7)0.0457 (5)
H2A0.55000.46970.73050.069*
O30.3264 (2)0.5208 (2)0.87512 (7)0.0379 (4)
O40.4087 (2)0.8337 (2)0.83451 (8)0.0399 (5)
H4A0.47330.74910.83750.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0292 (13)0.0453 (14)0.0348 (13)0.0003 (11)0.0008 (9)0.0016 (11)
C20.0364 (13)0.0527 (16)0.0414 (14)0.0028 (13)0.0020 (11)0.0047 (13)
C30.0437 (17)0.068 (2)0.0415 (16)0.0005 (16)0.0060 (12)0.0022 (15)
C40.0442 (15)0.0602 (18)0.0419 (15)0.0067 (15)0.0003 (12)0.0073 (14)
C50.0392 (14)0.0465 (15)0.0497 (14)0.0038 (13)0.0023 (12)0.0003 (13)
C60.0359 (13)0.0447 (14)0.0365 (13)0.0040 (12)0.0003 (10)0.0017 (11)
C70.0304 (12)0.0401 (13)0.0403 (14)0.0008 (12)0.0056 (10)0.0027 (11)
C80.0416 (14)0.0392 (14)0.0309 (12)0.0057 (12)0.0009 (10)0.0034 (11)
C90.0377 (13)0.0359 (13)0.0392 (14)0.0035 (11)0.0040 (10)0.0000 (11)
C100.0413 (15)0.0427 (15)0.0530 (16)0.0034 (12)0.0150 (12)0.0005 (13)
C110.0357 (14)0.0434 (14)0.0496 (15)0.0040 (12)0.0096 (11)0.0032 (12)
C120.0291 (12)0.0417 (14)0.0439 (14)0.0010 (11)0.0026 (10)0.0051 (11)
C130.0400 (13)0.0424 (14)0.0356 (13)0.0005 (12)0.0045 (12)0.0024 (11)
C140.0498 (17)0.0432 (15)0.0606 (19)0.0065 (14)0.0043 (13)0.0036 (14)
C150.0659 (18)0.0500 (16)0.0424 (15)0.0027 (15)0.0073 (14)0.0058 (14)
O10.0418 (11)0.0471 (11)0.0578 (12)0.0067 (9)0.0070 (9)0.0048 (10)
O20.0565 (12)0.0472 (11)0.0335 (9)0.0081 (10)0.0042 (8)0.0019 (8)
O30.0353 (9)0.0425 (10)0.0357 (9)0.0031 (8)0.0013 (7)0.0002 (8)
O40.0378 (10)0.0409 (10)0.0410 (9)0.0051 (8)0.0035 (7)0.0026 (9)
Geometric parameters (Å, º) top
C1—C61.399 (4)C10—C111.526 (4)
C1—C21.403 (4)C10—H10A0.9900
C1—C71.488 (4)C10—H10B0.9900
C2—C31.380 (4)C11—C121.513 (4)
C2—H20.9500C11—H11A0.9900
C3—C41.376 (5)C11—H11B0.9900
C3—H30.9500C12—O31.441 (3)
C4—C51.389 (4)C12—C131.516 (4)
C4—H40.9500C12—H121.0000
C5—C61.383 (4)C13—O41.446 (3)
C5—H50.9500C13—C141.528 (4)
C6—H60.9500C13—C151.530 (4)
C7—O11.223 (4)C14—H14A0.9800
C7—C81.523 (4)C14—H14B0.9800
C8—O21.413 (3)C14—H14C0.9800
C8—C91.543 (4)C15—H15A0.9800
C8—H81.0000C15—H15B0.9800
C9—O31.438 (3)C15—H15C0.9800
C9—C101.533 (4)O2—H2A0.8400
C9—H91.0000O4—H4A0.8400
C6—C1—C2118.6 (3)C11—C10—H10B111.3
C6—C1—C7123.2 (2)C9—C10—H10B111.3
C2—C1—C7118.2 (3)H10A—C10—H10B109.2
C3—C2—C1120.3 (3)C12—C11—C10103.2 (2)
C3—C2—H2119.8C12—C11—H11A111.1
C1—C2—H2119.8C10—C11—H11A111.1
C4—C3—C2120.6 (3)C12—C11—H11B111.1
C4—C3—H3119.7C10—C11—H11B111.1
C2—C3—H3119.7H11A—C11—H11B109.1
C3—C4—C5120.1 (3)O3—C12—C11106.0 (2)
C3—C4—H4120.0O3—C12—C13107.3 (2)
C5—C4—H4120.0C11—C12—C13117.2 (2)
C6—C5—C4119.9 (3)O3—C12—H12108.7
C6—C5—H5120.0C11—C12—H12108.7
C4—C5—H5120.0C13—C12—H12108.7
C5—C6—C1120.6 (3)O4—C13—C12110.0 (2)
C5—C6—H6119.7O4—C13—C14106.0 (2)
C1—C6—H6119.7C12—C13—C14110.3 (2)
O1—C7—C1121.4 (2)O4—C13—C15108.3 (2)
O1—C7—C8119.2 (2)C12—C13—C15111.1 (2)
C1—C7—C8119.3 (2)C14—C13—C15110.9 (2)
O2—C8—C7109.6 (2)C13—C14—H14A109.5
O2—C8—C9111.3 (2)C13—C14—H14B109.5
C7—C8—C9107.8 (2)H14A—C14—H14B109.5
O2—C8—H8109.4C13—C14—H14C109.5
C7—C8—H8109.4H14A—C14—H14C109.5
C9—C8—H8109.4H14B—C14—H14C109.5
O3—C9—C10106.3 (2)C13—C15—H15A109.5
O3—C9—C8109.1 (2)C13—C15—H15B109.5
C10—C9—C8114.2 (2)H15A—C15—H15B109.5
O3—C9—H9109.1C13—C15—H15C109.5
C10—C9—H9109.1H15A—C15—H15C109.5
C8—C9—H9109.1H15B—C15—H15C109.5
C11—C10—C9102.6 (2)C8—O2—H2A109.5
C11—C10—H10A111.3C9—O3—C12110.46 (19)
C9—C10—H10A111.3C13—O4—H4A109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O4i0.841.882.707 (3)170
O4—H4A···O30.842.312.756 (3)113
O4—H4A···O10.842.333.131 (3)161
O4—H4A···O20.842.583.186 (3)130
Symmetry code: (i) x+1, y1/2, z+3/2.
 

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