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In the structure of the title compound, C15H20O3, the molecular conformation is supported by a strong intramol­ecular hydrogen-bond contact. A second strong intermol­ecular hydrogen bond connects the mol­ecules to form infinite zigzag chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006646/su6087sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006646/su6087Isup2.hkl
Contains datablock I

CCDC reference: 238816

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.119
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C15H20O3F(000) = 536
Mr = 248.31Dx = 1.228 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 1924 reflections
a = 10.391 (1) Åθ = 0–70°
b = 12.553 (2) ŵ = 0.68 mm1
c = 11.773 (1) ÅT = 150 K
β = 118.961 (10)°Prism, colourless
V = 1343.6 (3) Å30.38 × 0.15 × 0.15 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2070 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Horizontally mounted graphite crystal monochromatorθmax = 68.3°, θmin = 4.9°
Detector resolution: 9 pixels mm-1h = 1212
φ or ω [please specify] scansk = 1514
4716 measured reflectionsl = 1414
2452 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0676P)2 + 0.5821P]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
2452 reflectionsΔρmax = 0.25 e Å3
244 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0050 (9)
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
O20.82044 (10)0.07748 (7)0.33967 (9)0.0274 (3)
O10.85142 (11)0.08046 (8)0.19881 (10)0.0304 (3)
O30.96542 (12)0.28225 (9)0.33593 (11)0.0391 (3)
C40.90346 (16)0.20864 (11)0.23269 (14)0.0292 (3)
H410.8610 (16)0.2461 (12)0.1484 (15)0.025 (4)*
C51.01049 (16)0.12797 (12)0.23052 (15)0.0318 (4)
C60.94201 (17)0.05811 (12)0.11227 (15)0.0324 (4)
H611.0098 (18)0.0044 (14)0.1133 (15)0.035 (4)*
H620.9122 (19)0.1011 (14)0.0328 (17)0.040 (4)*
C10.80535 (15)0.00034 (11)0.09851 (13)0.0281 (3)
C20.70022 (15)0.07845 (12)0.11149 (13)0.0283 (3)
H220.6212 (18)0.0378 (14)0.1161 (15)0.035 (4)*
H210.6587 (17)0.1239 (13)0.0346 (16)0.030 (4)*
C30.77268 (14)0.15060 (11)0.23241 (12)0.0247 (3)
C151.14888 (18)0.12077 (15)0.32209 (18)0.0432 (4)
H1511.216 (2)0.0675 (15)0.3165 (18)0.051 (5)*
H1521.191 (2)0.1704 (16)0.3985 (19)0.051 (5)*
C70.72783 (19)0.06084 (15)0.02887 (16)0.0414 (4)
H710.647 (2)0.1029 (16)0.0305 (19)0.058 (6)*
H720.793 (2)0.1121 (15)0.0365 (18)0.049 (5)*
H730.693 (2)0.0102 (16)0.1020 (19)0.051 (5)*
C80.90171 (19)0.12047 (14)0.46823 (14)0.0368 (4)
H820.8853 (19)0.0693 (14)0.5251 (17)0.043 (5)*
H830.863 (2)0.1915 (16)0.4734 (18)0.047 (5)*
H811.009 (2)0.1272 (15)0.4948 (18)0.048 (5)*
C90.65644 (15)0.22742 (11)0.22922 (13)0.0290 (3)
C140.57204 (17)0.20022 (14)0.28695 (16)0.0371 (4)
H1410.5942 (19)0.1348 (15)0.3358 (17)0.043 (5)*
C130.45844 (18)0.26636 (16)0.27563 (19)0.0471 (5)
H1310.404 (2)0.2444 (16)0.320 (2)0.054 (5)*
C120.42807 (19)0.35982 (16)0.20647 (18)0.0496 (5)
H1210.352 (2)0.4070 (17)0.196 (2)0.063 (6)*
C110.5102 (2)0.38736 (16)0.14825 (19)0.0529 (5)
H1110.487 (2)0.4532 (19)0.097 (2)0.065 (6)*
C100.62422 (19)0.32253 (14)0.16001 (16)0.0421 (4)
H1010.682 (2)0.3440 (16)0.1165 (19)0.057 (5)*
H10.871 (3)0.0483 (19)0.269 (2)0.066 (7)*
H31.022 (3)0.3252 (19)0.316 (2)0.070 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0366 (6)0.0255 (5)0.0235 (5)0.0006 (4)0.0174 (4)0.0007 (4)
O10.0345 (6)0.0257 (5)0.0334 (6)0.0027 (4)0.0182 (5)0.0002 (4)
O30.0459 (7)0.0318 (6)0.0509 (7)0.0141 (5)0.0325 (6)0.0135 (5)
C40.0371 (8)0.0254 (7)0.0331 (8)0.0016 (6)0.0232 (6)0.0011 (6)
C50.0367 (8)0.0294 (7)0.0397 (8)0.0029 (6)0.0267 (7)0.0004 (6)
C60.0408 (8)0.0319 (8)0.0357 (8)0.0054 (6)0.0275 (7)0.0014 (6)
C10.0313 (7)0.0289 (7)0.0246 (7)0.0050 (6)0.0139 (6)0.0005 (6)
C20.0303 (7)0.0292 (8)0.0259 (7)0.0043 (6)0.0139 (6)0.0012 (6)
C30.0302 (7)0.0239 (7)0.0236 (7)0.0019 (5)0.0159 (6)0.0008 (5)
C150.0330 (8)0.0456 (10)0.0546 (11)0.0034 (7)0.0240 (8)0.0079 (8)
C70.0391 (9)0.0471 (10)0.0319 (9)0.0092 (8)0.0125 (7)0.0110 (7)
C80.0488 (10)0.0387 (9)0.0245 (8)0.0004 (7)0.0192 (7)0.0005 (6)
C90.0310 (7)0.0286 (7)0.0278 (7)0.0007 (6)0.0146 (6)0.0062 (6)
C140.0364 (8)0.0367 (9)0.0450 (9)0.0030 (7)0.0251 (7)0.0086 (7)
C130.0369 (9)0.0556 (11)0.0572 (11)0.0048 (8)0.0294 (8)0.0213 (9)
C120.0376 (9)0.0519 (11)0.0519 (10)0.0128 (8)0.0159 (8)0.0174 (8)
C110.0584 (11)0.0455 (11)0.0531 (11)0.0218 (9)0.0257 (9)0.0023 (9)
C100.0504 (10)0.0367 (9)0.0454 (9)0.0122 (7)0.0281 (8)0.0050 (7)
Geometric parameters (Å, º) top
O2—C81.4344 (18)C15—H1510.99 (2)
O2—C31.4410 (15)C15—H1521.00 (2)
O1—C11.4449 (16)C7—H710.98 (2)
O1—H10.85 (2)C7—H720.97 (2)
O3—C41.4100 (17)C7—H730.99 (2)
O3—H30.91 (2)C8—H821.000 (19)
C4—C51.513 (2)C8—H830.99 (2)
C4—C31.5404 (18)C8—H811.001 (19)
C4—H410.988 (16)C9—C141.387 (2)
C5—C151.318 (2)C9—C101.392 (2)
C5—C61.501 (2)C14—C131.396 (2)
C6—C11.536 (2)C14—H1410.965 (19)
C6—H610.971 (17)C13—C121.375 (3)
C6—H620.991 (18)C13—H1310.97 (2)
C1—C71.518 (2)C12—C111.373 (3)
C1—C21.5351 (18)C12—H1210.95 (2)
C2—C31.5414 (18)C11—C101.388 (2)
C2—H220.991 (17)C11—H1110.98 (2)
C2—H210.976 (16)C10—H1010.99 (2)
C3—C91.5317 (18)
C8—O2—C3117.52 (11)C4—C3—C2108.41 (10)
C1—O1—H1107.0 (15)C5—C15—H151121.2 (11)
C4—O3—H3104.4 (14)C5—C15—H152121.4 (11)
O3—C4—C5114.87 (12)H151—C15—H152117.4 (15)
O3—C4—C3110.23 (11)C1—C7—H71109.1 (12)
C5—C4—C3109.77 (11)C1—C7—H72111.2 (11)
O3—C4—H41110.5 (9)H71—C7—H72105.8 (16)
C5—C4—H41106.0 (9)C1—C7—H73109.6 (11)
C3—C4—H41105.0 (9)H71—C7—H73112.1 (16)
C15—C5—C6123.91 (14)H72—C7—H73109.0 (15)
C15—C5—C4123.49 (14)O2—C8—H82105.1 (10)
C6—C5—C4112.60 (12)O2—C8—H83110.6 (11)
C5—C6—C1112.08 (11)H82—C8—H83109.2 (14)
C5—C6—H61112.3 (10)O2—C8—H81111.0 (11)
C1—C6—H61107.3 (10)H82—C8—H81111.6 (15)
C5—C6—H62110.4 (10)H83—C8—H81109.3 (15)
C1—C6—H62108.1 (10)C14—C9—C10117.90 (14)
H61—C6—H62106.5 (14)C14—C9—C3120.74 (13)
O1—C1—C7105.46 (12)C10—C9—C3121.18 (13)
O1—C1—C2109.71 (11)C9—C14—C13120.86 (17)
C7—C1—C2110.97 (12)C9—C14—H141118.5 (11)
O1—C1—C6108.83 (11)C13—C14—H141120.7 (11)
C7—C1—C6111.38 (12)C12—C13—C14120.34 (17)
C2—C1—C6110.35 (12)C12—C13—H131122.2 (12)
C1—C2—C3114.69 (11)C14—C13—H131117.5 (12)
C1—C2—H22108.8 (10)C11—C12—C13119.39 (16)
C3—C2—H22107.4 (9)C11—C12—H121117.7 (13)
C1—C2—H21107.5 (9)C13—C12—H121122.9 (13)
C3—C2—H21108.2 (9)C12—C11—C10120.64 (18)
H22—C2—H21110.3 (13)C12—C11—H111119.7 (12)
O2—C3—C9110.82 (10)C10—C11—H111119.6 (13)
O2—C3—C4111.73 (11)C11—C10—C9120.87 (16)
C9—C3—C4112.75 (11)C11—C10—H101119.1 (12)
O2—C3—C2104.00 (10)C9—C10—H101120.0 (12)
C9—C3—C2108.69 (11)
O3—C4—C5—C154.7 (2)O3—C4—C3—C2175.11 (11)
C3—C4—C5—C15120.19 (16)C5—C4—C3—C257.39 (14)
O3—C4—C5—C6174.78 (11)C1—C2—C3—O264.18 (14)
C3—C4—C5—C660.35 (15)C1—C2—C3—C9177.72 (11)
C15—C5—C6—C1124.06 (16)C1—C2—C3—C454.84 (15)
C4—C5—C6—C156.48 (16)O2—C3—C9—C1423.55 (18)
C5—C6—C1—O170.46 (15)C4—C3—C9—C14149.63 (13)
C5—C6—C1—C7173.69 (13)C2—C3—C9—C1490.15 (15)
C5—C6—C1—C249.97 (16)O2—C3—C9—C10161.54 (13)
O1—C1—C2—C368.96 (15)C4—C3—C9—C1035.46 (18)
C7—C1—C2—C3174.90 (13)C2—C3—C9—C1084.76 (16)
C6—C1—C2—C350.95 (16)C10—C9—C14—C130.1 (2)
C8—O2—C3—C967.23 (15)C3—C9—C14—C13175.02 (14)
C8—O2—C3—C459.42 (14)C9—C14—C13—C120.2 (3)
C8—O2—C3—C2176.14 (11)C14—C13—C12—C110.2 (3)
O3—C4—C3—O270.86 (14)C13—C12—C11—C100.8 (3)
C5—C4—C3—O256.64 (14)C12—C11—C10—C91.0 (3)
O3—C4—C3—C954.73 (15)C14—C9—C10—C110.6 (2)
C5—C4—C3—C9177.77 (11)C3—C9—C10—C11174.41 (15)
 

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