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The asymmetric unit of the title compound, C15H19FO4, contains two independent mol­ecules that hydrogen bond to form dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017019/na6099sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017019/na6099Isup2.hkl
Contains datablock I

CCDC reference: 177217

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.049
  • wR factor = 0.113
  • Data-to-parameter ratio = 13.3

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 5012 Count of symmetry unique reflns 2630 Completeness (_total/calc) 190.57% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2382 Fraction of Friedel pairs measured 0.906 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).

(2S)-1-(4-fluorophenyl)-2-hydroxy-2-[(2S,5R)-5-(1-hydroxy-1-methylethyl)- tetrahydrofuran-2-yl]ethanone top
Crystal data top
C15H19FO4Dx = 1.292 Mg m3
Mr = 282.30Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 23180 reflections
a = 10.973 (2) Åθ = 3.1–25.0°
b = 12.764 (3) ŵ = 0.10 mm1
c = 20.721 (4) ÅT = 150 K
V = 2902.2 (10) Å3Block, colourless
Z = 80.10 × 0.10 × 0.10 mm
F(000) = 1200
Data collection top
Nonius Kappa CCD area-detector
diffractometer
2859 reflections with I > 2σ(I)
Radiation source: Nonius FR591 Rotating anodeRint = 0.096
Graphite monochromatorθmax = 25.0°, θmin = 3.1°
Detector resolution: 9.091 pixels mm1 pixels mm-1h = 1113
φ and ω scans to fill the Ewald spherek = 1315
23180 measured reflectionsl = 2224
5012 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0381P)2]
where P = (Fo2 + 2Fc2)/3
5012 reflections(Δ/σ)max = 0.048
378 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.16 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
H030.281 (5)0.455 (3)0.498 (3)0.12 (2)*
H050.378 (3)0.433 (3)0.606 (2)0.059 (14)*
H070.170 (4)0.317 (3)0.524 (3)0.12 (2)*
H010.101 (8)0.467 (7)0.390 (5)0.29 (5)*
F10.9054 (2)0.6714 (2)0.35904 (15)0.1113 (10)
O10.0690 (3)0.4227 (3)0.35724 (17)0.0885 (9)
O20.3240 (2)0.43508 (15)0.37016 (13)0.0562 (7)
O30.3327 (2)0.4025 (2)0.50992 (14)0.0688 (8)
O40.3905 (2)0.5942 (2)0.48140 (15)0.0830 (9)
C10.0825 (4)0.3644 (3)0.2500 (2)0.0832 (14)
H1A0.00550.39930.23950.125*
H1B0.06610.29300.26500.125*
H1C0.13410.36180.21140.125*
C20.1712 (4)0.5381 (3)0.2822 (3)0.0938 (15)
H2A0.09350.57170.27160.141*
H2B0.22410.53830.24410.141*
H2C0.21090.57670.31730.141*
C30.1483 (3)0.4259 (3)0.3033 (2)0.0599 (10)
C40.2670 (3)0.3738 (2)0.3201 (2)0.0574 (10)
H40.32090.37350.28120.069*
C50.2618 (4)0.2636 (3)0.3481 (3)0.0923 (16)
H5A0.17990.24910.36600.111*
H5B0.27980.21100.31430.111*
C60.3559 (3)0.2594 (3)0.4002 (2)0.0666 (11)
H6A0.41890.20640.39010.080*
H6B0.31810.24180.44220.080*
C70.4108 (3)0.3688 (2)0.40180 (18)0.0525 (10)
H70.48820.36870.37630.063*
C80.4357 (3)0.4150 (3)0.46785 (19)0.0528 (9)
H80.50660.37730.48720.063*
C90.4672 (4)0.5305 (3)0.4633 (2)0.0590 (10)
C100.5834 (3)0.5647 (3)0.43559 (19)0.0531 (9)
C110.6798 (3)0.4960 (3)0.42333 (19)0.0556 (10)
H110.67090.42370.43320.067*
C120.7878 (4)0.5316 (3)0.3971 (2)0.0651 (11)
H120.85280.48470.38800.078*
C130.7984 (4)0.6350 (4)0.3849 (2)0.0742 (12)
C140.7092 (5)0.7064 (3)0.3978 (2)0.0851 (14)
H140.72150.77890.38970.102*
C150.5991 (4)0.6701 (3)0.4233 (2)0.0715 (12)
H150.53500.71800.43220.086*
F20.3763 (2)0.69292 (18)0.59889 (14)0.1072 (10)
O50.4228 (3)0.4280 (2)0.63817 (17)0.0687 (8)
O60.1594 (2)0.43280 (16)0.64255 (12)0.0544 (7)
O70.1263 (3)0.2666 (2)0.54482 (15)0.0730 (9)
O80.0838 (2)0.4567 (2)0.49763 (14)0.0752 (8)
C160.4304 (4)0.4763 (3)0.7483 (2)0.0838 (13)
H16A0.44710.40310.75960.126*
H16B0.38650.51020.78380.126*
H16C0.50750.51310.74070.126*
C170.3274 (4)0.5927 (3)0.6677 (3)0.0864 (14)
H17A0.27850.59360.62820.130*
H17B0.40470.62920.66010.130*
H17C0.28260.62810.70240.130*
C180.3527 (3)0.4802 (3)0.6872 (2)0.0569 (10)
C190.2337 (3)0.4215 (2)0.6987 (2)0.0542 (9)
H190.19070.45270.73670.065*
C200.2415 (3)0.3037 (2)0.7072 (2)0.0645 (11)
H20A0.30630.27350.67960.077*
H20B0.25790.28500.75270.077*
C210.1168 (3)0.2657 (3)0.6863 (2)0.0633 (11)
H21A0.06400.25280.72420.076*
H21B0.12340.20030.66090.076*
C220.0659 (3)0.3547 (2)0.64493 (19)0.0538 (9)
H220.00790.38460.66650.065*
C230.0346 (3)0.3272 (3)0.57498 (19)0.0567 (10)
H230.04250.28550.57500.068*
C240.0111 (3)0.4291 (3)0.5388 (2)0.0541 (10)
C250.0923 (3)0.4969 (3)0.55743 (19)0.0502 (9)
C260.2003 (3)0.4575 (3)0.58240 (19)0.0580 (10)
H260.20790.38440.59010.070*
C270.2960 (3)0.5227 (3)0.5961 (2)0.0622 (11)
H270.37030.49570.61270.075*
C280.2819 (4)0.6274 (3)0.5853 (2)0.0682 (12)
C290.1778 (4)0.6701 (3)0.5614 (2)0.0692 (11)
H290.17070.74360.55510.083*
C300.0824 (3)0.6037 (3)0.5466 (2)0.0630 (11)
H300.00940.63150.52880.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.102 (2)0.120 (2)0.112 (2)0.0515 (16)0.0059 (18)0.0066 (18)
O10.0553 (17)0.139 (3)0.072 (2)0.0022 (17)0.0102 (18)0.010 (2)
O20.0600 (16)0.0481 (12)0.0605 (18)0.0021 (12)0.0084 (13)0.0050 (12)
O30.0618 (18)0.0861 (19)0.0585 (19)0.0050 (15)0.0154 (16)0.0016 (15)
O40.0786 (19)0.0768 (17)0.094 (3)0.0223 (15)0.0129 (18)0.0191 (16)
C10.077 (3)0.100 (3)0.073 (4)0.010 (2)0.012 (3)0.021 (3)
C20.120 (4)0.069 (3)0.093 (4)0.001 (2)0.032 (3)0.015 (2)
C30.056 (2)0.077 (3)0.047 (3)0.0027 (19)0.001 (2)0.003 (2)
C40.057 (2)0.060 (2)0.055 (3)0.0079 (18)0.002 (2)0.0071 (19)
C50.103 (4)0.057 (2)0.117 (4)0.009 (2)0.036 (3)0.003 (2)
C60.068 (3)0.051 (2)0.081 (3)0.0061 (17)0.007 (3)0.002 (2)
C70.046 (2)0.059 (2)0.053 (3)0.0054 (17)0.007 (2)0.0034 (18)
C80.043 (2)0.065 (2)0.050 (3)0.0081 (17)0.008 (2)0.0024 (19)
C90.058 (3)0.062 (2)0.057 (3)0.009 (2)0.005 (2)0.0032 (19)
C100.061 (2)0.046 (2)0.052 (3)0.0007 (17)0.010 (2)0.0000 (17)
C110.054 (2)0.053 (2)0.060 (3)0.0028 (18)0.010 (2)0.0045 (18)
C120.059 (3)0.068 (2)0.068 (3)0.0102 (19)0.002 (2)0.004 (2)
C130.066 (3)0.089 (3)0.068 (3)0.028 (3)0.006 (2)0.003 (2)
C140.110 (4)0.059 (3)0.086 (4)0.015 (3)0.015 (3)0.009 (2)
C150.081 (3)0.066 (3)0.067 (3)0.007 (2)0.011 (3)0.002 (2)
F20.0923 (17)0.0889 (16)0.140 (3)0.0324 (14)0.0103 (19)0.0046 (16)
O50.0529 (17)0.095 (2)0.058 (2)0.0003 (14)0.0054 (18)0.0081 (17)
O60.0567 (15)0.0523 (13)0.0542 (18)0.0049 (11)0.0057 (14)0.0066 (11)
O70.0700 (19)0.0668 (17)0.082 (2)0.0047 (15)0.0121 (18)0.0201 (17)
O80.0657 (19)0.103 (2)0.057 (2)0.0025 (15)0.0132 (16)0.0101 (16)
C160.066 (3)0.120 (3)0.065 (3)0.019 (2)0.012 (3)0.022 (3)
C170.094 (3)0.063 (3)0.102 (4)0.021 (2)0.001 (3)0.007 (2)
C180.053 (2)0.066 (2)0.052 (3)0.0069 (18)0.000 (2)0.015 (2)
C190.055 (2)0.057 (2)0.051 (3)0.0015 (17)0.003 (2)0.0017 (18)
C200.068 (3)0.067 (2)0.058 (3)0.0040 (19)0.009 (2)0.010 (2)
C210.060 (3)0.055 (2)0.075 (3)0.0068 (17)0.003 (2)0.007 (2)
C220.049 (2)0.052 (2)0.060 (3)0.0081 (17)0.004 (2)0.0005 (19)
C230.046 (2)0.064 (2)0.059 (3)0.0068 (17)0.002 (2)0.013 (2)
C240.048 (2)0.068 (2)0.046 (3)0.0114 (18)0.002 (2)0.0056 (19)
C250.046 (2)0.055 (2)0.050 (2)0.0055 (16)0.002 (2)0.0001 (17)
C260.052 (2)0.064 (2)0.058 (3)0.0017 (18)0.003 (2)0.0060 (19)
C270.049 (2)0.074 (3)0.064 (3)0.0006 (19)0.003 (2)0.007 (2)
C280.061 (3)0.073 (3)0.071 (3)0.010 (2)0.000 (2)0.003 (2)
C290.077 (3)0.061 (2)0.070 (3)0.002 (2)0.002 (3)0.007 (2)
C300.057 (2)0.071 (3)0.061 (3)0.009 (2)0.001 (2)0.004 (2)
Geometric parameters (Å, º) top
F1—C131.372 (5)F2—C281.360 (4)
O1—C31.417 (5)O5—C181.437 (4)
O1—H010.95 (10)O5—H050.83 (4)
O2—C71.433 (4)O6—C191.429 (4)
O2—C41.441 (4)O6—C221.431 (3)
O3—C81.436 (4)O7—C231.414 (4)
O3—H030.91 (4)O7—H070.91 (5)
O4—C91.229 (4)O8—C241.219 (4)
C1—C31.536 (5)C16—C181.528 (5)
C1—H1A0.9800C16—H16A0.9800
C1—H1B0.9800C16—H16B0.9800
C1—H1C0.9800C16—H16C0.9800
C2—C31.518 (5)C17—C181.518 (5)
C2—H2A0.9800C17—H17A0.9800
C2—H2B0.9800C17—H17B0.9800
C2—H2C0.9800C17—H17C0.9800
C3—C41.503 (5)C18—C191.524 (5)
C4—C51.522 (4)C19—C201.516 (4)
C4—H41.0000C19—H191.0000
C5—C61.495 (5)C20—C211.515 (5)
C5—H5A0.9900C20—H20A0.9900
C5—H5B0.9900C20—H20B0.9900
C6—C71.521 (4)C21—C221.528 (5)
C6—H6A0.9900C21—H21A0.9900
C6—H6B0.9900C21—H21B0.9900
C7—C81.515 (5)C22—C231.530 (5)
C7—H71.0000C22—H221.0000
C8—C91.517 (5)C23—C241.524 (5)
C8—H81.0000C23—H231.0000
C9—C101.465 (5)C24—C251.478 (5)
C10—C151.380 (5)C25—C301.386 (4)
C10—C111.396 (5)C25—C261.388 (4)
C11—C121.381 (5)C26—C271.370 (5)
C11—H110.9500C26—H260.9500
C12—C131.349 (5)C27—C281.364 (5)
C12—H120.9500C27—H270.9500
C13—C141.364 (6)C28—C291.359 (5)
C14—C151.397 (6)C29—C301.381 (5)
C14—H140.9500C29—H290.9500
C15—H150.9500C30—H300.9500
C3—O1—H01108 (6)C18—O5—H05102 (3)
C7—O2—C4107.3 (2)C19—O6—C22108.1 (3)
C8—O3—H03105 (4)C23—O7—H07102 (3)
C3—C1—H1A109.5C18—C16—H16A109.5
C3—C1—H1B109.5C18—C16—H16B109.5
H1A—C1—H1B109.5H16A—C16—H16B109.5
C3—C1—H1C109.5C18—C16—H16C109.5
H1A—C1—H1C109.5H16A—C16—H16C109.5
H1B—C1—H1C109.5H16B—C16—H16C109.5
C3—C2—H2A109.5C18—C17—H17A109.5
C3—C2—H2B109.5C18—C17—H17B109.5
H2A—C2—H2B109.5H17A—C17—H17B109.5
C3—C2—H2C109.5C18—C17—H17C109.5
H2A—C2—H2C109.5H17A—C17—H17C109.5
H2B—C2—H2C109.5H17B—C17—H17C109.5
O1—C3—C4109.7 (3)O5—C18—C17110.4 (4)
O1—C3—C2110.9 (4)O5—C18—C19110.0 (3)
C4—C3—C2109.9 (3)C17—C18—C19110.5 (3)
O1—C3—C1105.3 (3)O5—C18—C16105.8 (3)
C4—C3—C1110.3 (3)C17—C18—C16110.7 (3)
C2—C3—C1110.6 (4)C19—C18—C16109.4 (3)
O2—C4—C3107.6 (3)O6—C19—C20103.1 (3)
O2—C4—C5104.1 (3)O6—C19—C18108.1 (3)
C3—C4—C5117.7 (3)C20—C19—C18117.2 (3)
O2—C4—H4109.1O6—C19—H19109.4
C3—C4—H4109.1C20—C19—H19109.4
C5—C4—H4109.1C18—C19—H19109.4
C6—C5—C4106.4 (3)C21—C20—C19103.4 (3)
C6—C5—H5A110.4C21—C20—H20A111.1
C4—C5—H5A110.4C19—C20—H20A111.1
C6—C5—H5B110.4C21—C20—H20B111.1
C4—C5—H5B110.4C19—C20—H20B111.1
H5A—C5—H5B108.6H20A—C20—H20B109.0
C5—C6—C7104.8 (3)C20—C21—C22104.7 (3)
C5—C6—H6A110.8C20—C21—H21A110.8
C7—C6—H6A110.8C22—C21—H21A110.8
C5—C6—H6B110.8C20—C21—H21B110.8
C7—C6—H6B110.8C22—C21—H21B110.8
H6A—C6—H6B108.9H21A—C21—H21B108.9
O2—C7—C8107.6 (3)O6—C22—C21106.0 (3)
O2—C7—C6105.6 (3)O6—C22—C23106.7 (3)
C8—C7—C6116.6 (3)C21—C22—C23116.3 (3)
O2—C7—H7108.9O6—C22—H22109.2
C8—C7—H7108.9C21—C22—H22109.2
C6—C7—H7108.9C23—C22—H22109.2
O3—C8—C7111.3 (3)O7—C23—C24111.7 (3)
O3—C8—C9109.0 (3)O7—C23—C22112.6 (3)
C7—C8—C9111.3 (3)C24—C23—C22108.0 (3)
O3—C8—H8108.4O7—C23—H23108.1
C7—C8—H8108.4C24—C23—H23108.1
C9—C8—H8108.4C22—C23—H23108.1
O4—C9—C10121.3 (3)O8—C24—C25121.1 (3)
O4—C9—C8117.9 (3)O8—C24—C23118.7 (3)
C10—C9—C8120.8 (3)C25—C24—C23120.1 (3)
C15—C10—C11118.9 (4)C30—C25—C26119.0 (3)
C15—C10—C9118.1 (3)C30—C25—C24118.2 (3)
C11—C10—C9123.0 (3)C26—C25—C24122.7 (3)
C12—C11—C10121.0 (3)C27—C26—C25120.7 (3)
C12—C11—H11119.5C27—C26—H26119.6
C10—C11—H11119.5C25—C26—H26119.6
C13—C12—C11118.0 (4)C28—C27—C26118.3 (3)
C13—C12—H12121.0C28—C27—H27120.8
C11—C12—H12121.0C26—C27—H27120.8
C12—C13—C14123.7 (4)C29—C28—F2118.0 (4)
C12—C13—F1118.5 (4)C29—C28—C27123.2 (4)
C14—C13—F1117.7 (4)F2—C28—C27118.8 (4)
C13—C14—C15118.3 (4)C28—C29—C30118.2 (4)
C13—C14—H14120.9C28—C29—H29120.9
C15—C14—H14120.9C30—C29—H29120.9
C10—C15—C14120.0 (4)C29—C30—C25120.5 (3)
C10—C15—H15120.0C29—C30—H30119.7
C14—C15—H15120.0C25—C30—H30119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H05···O30.83 (4)2.09 (4)2.854 (5)153 (3)
O7—H07···O30.91 (5)2.11 (4)2.943 (4)150 (4)
O1—H01···O80.95 (10)2.25 (11)2.946 (5)130 (7)
O3—H03···O80.93 (8)2.17 (9)2.831 (5)127 (6)
 

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