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The title compound, C14H20O2, was synthesized by the reaction of phenol and octa­noyl chloride. All non-H atoms are coplanar, with an r.m.s. deviation of 0.031 Å. In the crystal structure, mol­ecules are linked into chains along the a axis by inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009925/ci2027sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009925/ci2027Isup2.hkl
Contains datablock I

CCDC reference: 608585

Key indicators

  • Single-crystal X-ray study
  • T = 288 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.060
  • wR factor = 0.170
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.43 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1-(2-hydroxyphenyl)octanone top
Crystal data top
C14H20O2Z = 2
Mr = 220.30F(000) = 240
Triclinic, P1Dx = 1.124 Mg m3
Hall symbol: -P 1Melting point: 294 K K
a = 6.8560 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.4850 (17) ÅCell parameters from 25 reflections
c = 11.547 (2) Åθ = 10–13°
α = 95.20 (3)°µ = 0.07 mm1
β = 102.54 (3)°T = 288 K
γ = 93.15 (3)°Block, light yellow
V = 651.1 (2) Å30.40 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1229 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 26.0°, θmin = 1.8°
ω/2θ scansh = 08
Absorption correction: ψ scan
(North et al., 1968)
k = 1010
Tmin = 0.971, Tmax = 0.986l = 1413
2781 measured reflections3 standard reflections every 200 reflections
2555 independent reflections intensity decay: none
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)] = 0.060H-atom parameters constrained
wR(F2) = 0.170 w = 1/[σ2(Fo2) + (0.07P)2 + 0.02P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2555 reflectionsΔρmax = 0.14 e Å3
146 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.029 (6)
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
O10.2599 (2)1.1164 (2)0.79697 (16)0.0762 (6)
O20.4406 (2)0.9798 (2)0.65026 (16)0.0860 (7)
H2A0.42781.04190.70630.129*
C10.5829 (5)1.4578 (4)1.2579 (3)0.0980 (11)
H1A0.56371.54031.32280.147*
H1B0.61341.35781.28530.147*
H1C0.69171.47991.19520.147*
C20.3931 (4)1.4505 (3)1.2111 (2)0.0716 (8)
H2B0.36091.55311.18620.086*
H2C0.28361.42981.27530.086*
C30.4086 (4)1.3258 (3)1.1082 (2)0.0610 (7)
H3A0.51941.34571.04450.073*
H3B0.43921.22311.13350.073*
C40.2205 (4)1.3190 (3)1.0597 (2)0.0608 (7)
H4A0.18961.42171.03450.073*
H4B0.10971.29861.12320.073*
C50.2382 (4)1.1932 (3)0.9558 (2)0.0598 (7)
H5A0.34981.21360.89280.072*
H5B0.26921.09080.98140.072*
C60.0522 (4)1.1842 (3)0.9051 (2)0.0585 (7)
H6A0.02111.28580.87830.070*
H6B0.06011.16320.96750.070*
C70.0786 (3)1.0561 (3)0.8020 (2)0.0542 (7)
H7A0.11710.95610.82850.065*
H7B0.18821.08020.73900.065*
C80.1032 (3)1.0353 (3)0.7505 (2)0.0518 (6)
C90.0935 (3)0.9179 (3)0.6472 (2)0.0464 (6)
C100.0825 (4)0.8275 (3)0.5918 (2)0.0550 (7)
H10A0.19800.84140.62030.066*
C110.0892 (4)0.7179 (3)0.4954 (2)0.0670 (8)
H11A0.20810.65810.45900.080*
C120.0832 (4)0.6972 (3)0.4529 (2)0.0685 (8)
H12A0.08030.62240.38840.082*
C130.2568 (4)0.7863 (3)0.5056 (2)0.0682 (8)
H13A0.37120.77290.47600.082*
C140.2643 (4)0.8959 (3)0.6022 (2)0.0569 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0440 (11)0.0953 (15)0.0809 (13)0.0105 (10)0.0136 (9)0.0248 (11)
O20.0407 (11)0.1209 (17)0.0946 (15)0.0048 (11)0.0255 (10)0.0173 (12)
C10.090 (2)0.114 (3)0.101 (2)0.020 (2)0.051 (2)0.009 (2)
C20.0758 (19)0.0687 (19)0.0745 (18)0.0101 (15)0.0317 (15)0.0087 (15)
C30.0563 (16)0.0619 (17)0.0656 (16)0.0073 (13)0.0193 (13)0.0037 (13)
C40.0537 (16)0.0654 (17)0.0627 (16)0.0074 (13)0.0173 (13)0.0089 (13)
C50.0503 (15)0.0659 (17)0.0626 (17)0.0052 (13)0.0158 (13)0.0053 (13)
C60.0507 (15)0.0644 (17)0.0593 (15)0.0077 (13)0.0146 (12)0.0070 (13)
C70.0449 (14)0.0622 (17)0.0551 (15)0.0039 (12)0.0144 (12)0.0028 (12)
C80.0397 (14)0.0585 (16)0.0567 (15)0.0053 (12)0.0094 (12)0.0059 (13)
C90.0405 (13)0.0513 (15)0.0489 (14)0.0047 (11)0.0141 (11)0.0025 (11)
C100.0489 (15)0.0561 (16)0.0620 (16)0.0013 (12)0.0202 (12)0.0007 (13)
C110.0633 (18)0.0629 (18)0.0717 (18)0.0049 (14)0.0176 (15)0.0091 (14)
C120.084 (2)0.0586 (18)0.0676 (18)0.0177 (16)0.0283 (16)0.0019 (14)
C130.0614 (19)0.079 (2)0.0718 (19)0.0223 (16)0.0283 (15)0.0075 (16)
C140.0430 (15)0.0684 (18)0.0615 (16)0.0067 (13)0.0171 (13)0.0042 (14)
Geometric parameters (Å, º) top
O1—C81.232 (3)C5—H5B0.97
O2—C141.348 (3)C6—C71.510 (3)
O2—H2A0.82C6—H6A0.97
C1—C21.516 (3)C6—H6B0.97
C1—H1A0.96C7—C81.505 (3)
C1—H1B0.96C7—H7A0.97
C1—H1C0.96C7—H7B0.97
C2—C31.499 (3)C8—C91.470 (3)
C2—H2B0.97C9—C101.388 (3)
C2—H2C0.97C9—C141.395 (3)
C3—C41.516 (3)C10—C111.375 (3)
C3—H3A0.97C10—H10A0.93
C3—H3B0.97C11—C121.388 (3)
C4—C51.511 (3)C11—H11A0.93
C4—H4A0.97C12—C131.365 (4)
C4—H4B0.97C12—H12A0.93
C5—C61.517 (3)C13—C141.376 (3)
C5—H5A0.97C13—H13A0.93
C14—O2—H2A109.5C7—C6—H6A109.2
C2—C1—H1A109.5C5—C6—H6A109.2
C2—C1—H1B109.5C7—C6—H6B109.2
H1A—C1—H1B109.5C5—C6—H6B109.2
C2—C1—H1C109.5H6A—C6—H6B107.9
H1A—C1—H1C109.5C8—C7—C6115.2 (2)
H1B—C1—H1C109.5C8—C7—H7A108.5
C3—C2—C1113.6 (2)C6—C7—H7A108.5
C3—C2—H2B108.9C8—C7—H7B108.5
C1—C2—H2B108.9C6—C7—H7B108.5
C3—C2—H2C108.9H7A—C7—H7B107.5
C1—C2—H2C108.9O1—C8—C9120.8 (2)
H2B—C2—H2C107.7O1—C8—C7119.0 (2)
C2—C3—C4114.0 (2)C9—C8—C7120.1 (2)
C2—C3—H3A108.8C10—C9—C14118.4 (2)
C4—C3—H3A108.8C10—C9—C8121.8 (2)
C2—C3—H3B108.8C14—C9—C8119.8 (2)
C4—C3—H3B108.8C11—C10—C9121.2 (2)
H3A—C3—H3B107.7C11—C10—H10A119.4
C5—C4—C3113.5 (2)C9—C10—H10A119.4
C5—C4—H4A108.9C10—C11—C12119.4 (3)
C3—C4—H4A108.9C10—C11—H11A120.3
C5—C4—H4B108.9C12—C11—H11A120.3
C3—C4—H4B108.9C13—C12—C11120.2 (3)
H4A—C4—H4B107.7C13—C12—H12A119.9
C4—C5—C6114.6 (2)C11—C12—H12A119.9
C4—C5—H5A108.6C12—C13—C14120.6 (3)
C6—C5—H5A108.6C12—C13—H13A119.7
C4—C5—H5B108.6C14—C13—H13A119.7
C6—C5—H5B108.6O2—C14—C13117.7 (2)
H5A—C5—H5B107.6O2—C14—C9122.1 (2)
C7—C6—C5112.2 (2)C13—C14—C9120.2 (2)
C1—C2—C3—C4179.2 (2)C14—C9—C10—C110.5 (4)
C2—C3—C4—C5179.8 (2)C8—C9—C10—C11179.9 (2)
C3—C4—C5—C6179.8 (2)C9—C10—C11—C120.0 (4)
C4—C5—C6—C7179.8 (2)C10—C11—C12—C130.8 (4)
C5—C6—C7—C8177.4 (2)C11—C12—C13—C140.9 (4)
C6—C7—C8—O12.9 (3)C12—C13—C14—O2179.9 (2)
C6—C7—C8—C9178.0 (2)C12—C13—C14—C90.3 (4)
O1—C8—C9—C10178.6 (2)C10—C9—C14—O2179.4 (2)
C7—C8—C9—C102.3 (3)C8—C9—C14—O20.2 (4)
O1—C8—C9—C141.0 (4)C10—C9—C14—C130.4 (4)
C7—C8—C9—C14178.1 (2)C8—C9—C14—C13180.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.821.822.542 (2)146
C7—H7B···O2i0.972.593.377 (3)138
Symmetry code: (i) x1, y, z.
 

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