organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-[2-(3,5-Di­fluoro­benz­yl­oxy)phen­yl]ethanone

aCollege of Science, Northwest A&F University, Yangling 712100, People's Republic of China
*Correspondence e-mail: jinminggaocn@yahoo.com.cn

(Received 22 July 2010; accepted 4 August 2010; online 11 August 2010)

In the title compound, C15H12F2O2, the dihedral angle between the aromatic rings is 70.43 (4)°. The crystal packing exhibits no significantly short inter­molecular contacts.

Related literature

For background to the Williamson reaction in organic synthesis, see: Dermer (1934[Dermer, O. C. (1934). Chem. Rev. 14, 385-430.]). For a related structure, see: Ma et al. (2010[Ma, Y.-T., Wang, J.-J., Liu, X.-W., Yang, S.-X. & Gao, J.-M. (2010). Acta Cryst. E66, o52.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12F2O2

  • Mr = 262.25

  • Triclinic, [P \overline 1]

  • a = 7.2808 (7) Å

  • b = 7.9734 (8) Å

  • c = 11.6466 (12) Å

  • α = 91.587 (1)°

  • β = 106.559 (2)°

  • γ = 95.343 (1)°

  • V = 644.22 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 298 K

  • 0.42 × 0.38 × 0.20 mm

Data collection
  • Bruker SMART CD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.956, Tmax = 0.979

  • 3373 measured reflections

  • 2239 independent reflections

  • 1402 reflections with I > 2σ(I)

  • Rint = 0.014

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.153

  • S = 1.03

  • 2239 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1996[Bruker (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1996[Bruker (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The Williamson reaction is a very useful transformation in organic synthesis since the products are of value in both industrial and academic applications. It usually involves the reaction of an alkali-metal salt of a hydroxy compound and an alkyl halide (Dermer, 1934). In the present paper, we present the structure of the title compound, C15H12F2O2 (I), which was synthesized by the reaction of 1-(2-hydroxyphenyl)ethanone, potassium carbonate and 3,5-difluorobenzyl bromide. We have previously reported the structure of a compound of this type (Ma et al., 2010). In (I) (Fig. 1), the ethanone group is close to coplanar with the benzene ring [torsion angle C4–C3–C2–O1, 178.8 (2)°] while the dihedral angle between the aromatic rings is 70.43 (4)°. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature top

For background to the Williamson reaction in organic synthesis, see: Dermer (1934). For a related structure, see: Ma et al. (2010).

Experimental top

1-(2-Hydroxyphenyl)ethanone (4 mmol), potassium carbonate (8 mmol), 3,5-difluorobenzyl bromide (4 mmol), and 40 ml acetone were mixed in a 100 ml flask. After 3 h stirring at 331 K, the crude product was obtained. Crystals of (I) were obtained by recrystallization from n-hexane/ethyl acetate.

Refinement top

The positions of all H atoms were determined geometrically and refined using a riding model with C—H = 0.93–0.97 Å and Uiso(methyl H) = 1.5Ueq(C) and 1.5Ueq for other H atoms.

Structure description top

The Williamson reaction is a very useful transformation in organic synthesis since the products are of value in both industrial and academic applications. It usually involves the reaction of an alkali-metal salt of a hydroxy compound and an alkyl halide (Dermer, 1934). In the present paper, we present the structure of the title compound, C15H12F2O2 (I), which was synthesized by the reaction of 1-(2-hydroxyphenyl)ethanone, potassium carbonate and 3,5-difluorobenzyl bromide. We have previously reported the structure of a compound of this type (Ma et al., 2010). In (I) (Fig. 1), the ethanone group is close to coplanar with the benzene ring [torsion angle C4–C3–C2–O1, 178.8 (2)°] while the dihedral angle between the aromatic rings is 70.43 (4)°. The crystal packing exhibits no significantly short intermolecular contacts.

For background to the Williamson reaction in organic synthesis, see: Dermer (1934). For a related structure, see: Ma et al. (2010).

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with atom labels, and displacement ellipsoids drawn at the 30% probability level.
1-[2-(3,5-Difluorobenzyloxy)phenyl]ethanone top
Crystal data top
C15H12F2O2Z = 2
Mr = 262.25F(000) = 272
Triclinic, P1Dx = 1.352 Mg m3
Hall symbol: -P 1Melting point = 347–348 K
a = 7.2808 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.9734 (8) ÅCell parameters from 1136 reflections
c = 11.6466 (12) Åθ = 2.9–24.8°
α = 91.587 (1)°µ = 0.11 mm1
β = 106.559 (2)°T = 298 K
γ = 95.343 (1)°Plate, colorless
V = 644.22 (11) Å30.42 × 0.38 × 0.20 mm
Data collection top
Bruker SMART CD area-detector
diffractometer
2239 independent reflections
Radiation source: fine-focus sealed tube1402 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.956, Tmax = 0.979k = 95
3373 measured reflectionsl = 1313
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) = 0.153H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0702P)2 + 0.1465P]
where P = (Fo2 + 2Fc2)/3
2239 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C15H12F2O2γ = 95.343 (1)°
Mr = 262.25V = 644.22 (11) Å3
Triclinic, P1Z = 2
a = 7.2808 (7) ÅMo Kα radiation
b = 7.9734 (8) ŵ = 0.11 mm1
c = 11.6466 (12) ÅT = 298 K
α = 91.587 (1)°0.42 × 0.38 × 0.20 mm
β = 106.559 (2)°
Data collection top
Bruker SMART CD area-detector
diffractometer
2239 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1402 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.979Rint = 0.014
3373 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.03Δρmax = 0.21 e Å3
2239 reflectionsΔρmin = 0.20 e Å3
173 parameters
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
F10.1438 (3)0.8789 (4)0.0404 (2)0.1646 (11)
F20.6758 (4)0.6785 (4)0.0348 (2)0.1880 (13)
O10.7550 (3)0.2045 (2)0.54230 (18)0.0964 (7)
O20.7176 (2)0.67975 (18)0.41603 (13)0.0629 (5)
C10.6631 (4)0.3400 (3)0.3629 (2)0.0627 (7)
H1A0.63210.22600.32920.094*
H1B0.75980.39650.33210.094*
H1C0.54950.39810.34160.094*
C20.7371 (3)0.3388 (3)0.4951 (2)0.0564 (6)
C30.7914 (3)0.4967 (3)0.57422 (19)0.0471 (5)
C40.7837 (3)0.6620 (3)0.53600 (19)0.0481 (5)
C50.8396 (3)0.7987 (3)0.6196 (2)0.0583 (6)
H50.83550.90800.59380.070*
C60.9010 (4)0.7728 (3)0.7398 (2)0.0659 (7)
H60.93790.86500.79500.079*
C70.9086 (4)0.6135 (3)0.7795 (2)0.0674 (7)
H70.95010.59660.86120.081*
C80.8540 (3)0.4786 (3)0.6971 (2)0.0590 (6)
H80.85920.37030.72470.071*
C90.7050 (4)0.8454 (3)0.3733 (2)0.0700 (7)
H9A0.83270.90480.38820.084*
H9B0.63200.90900.41380.084*
C100.6061 (4)0.8257 (3)0.2421 (2)0.0587 (6)
C110.4210 (4)0.8648 (3)0.1996 (2)0.0682 (7)
H110.35850.90690.25180.082*
C120.3289 (4)0.8415 (4)0.0801 (3)0.0856 (9)
C130.4081 (5)0.7794 (4)0.0002 (3)0.0902 (9)
H130.34050.76320.08110.108*
C140.5903 (6)0.7418 (5)0.0421 (3)0.0977 (10)
C150.6927 (5)0.7637 (4)0.1624 (3)0.0914 (9)
H150.81890.73650.18870.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0955 (15)0.243 (3)0.1260 (18)0.0644 (17)0.0240 (13)0.0392 (17)
F20.187 (3)0.284 (4)0.1253 (19)0.063 (2)0.0883 (18)0.035 (2)
O10.163 (2)0.0435 (11)0.0898 (14)0.0206 (11)0.0447 (13)0.0108 (10)
O20.0905 (12)0.0383 (9)0.0520 (10)0.0087 (8)0.0073 (8)0.0027 (7)
C10.0713 (16)0.0452 (13)0.0708 (16)0.0032 (11)0.0215 (13)0.0080 (11)
C20.0622 (15)0.0418 (13)0.0717 (16)0.0098 (10)0.0285 (12)0.0048 (11)
C30.0466 (12)0.0453 (12)0.0519 (13)0.0099 (9)0.0164 (10)0.0051 (10)
C40.0481 (12)0.0447 (12)0.0507 (13)0.0090 (9)0.0117 (10)0.0024 (10)
C50.0618 (15)0.0463 (13)0.0625 (15)0.0097 (11)0.0103 (12)0.0028 (11)
C60.0668 (16)0.0672 (17)0.0589 (16)0.0124 (12)0.0101 (12)0.0132 (12)
C70.0713 (17)0.0807 (19)0.0501 (14)0.0160 (14)0.0148 (12)0.0049 (13)
C80.0598 (14)0.0578 (15)0.0646 (16)0.0149 (11)0.0227 (12)0.0135 (12)
C90.0921 (19)0.0431 (13)0.0622 (15)0.0051 (12)0.0025 (13)0.0081 (11)
C100.0715 (16)0.0443 (13)0.0597 (15)0.0077 (11)0.0166 (12)0.0110 (11)
C110.0706 (18)0.0718 (17)0.0618 (16)0.0081 (13)0.0189 (13)0.0016 (12)
C120.0740 (19)0.099 (2)0.075 (2)0.0192 (16)0.0052 (16)0.0020 (16)
C130.102 (2)0.106 (2)0.0591 (18)0.0128 (19)0.0171 (17)0.0042 (16)
C140.117 (3)0.117 (3)0.076 (2)0.022 (2)0.052 (2)0.0050 (18)
C150.082 (2)0.105 (2)0.091 (2)0.0324 (17)0.0235 (17)0.0040 (18)
Geometric parameters (Å, º) top
F1—C121.359 (3)C6—H60.9300
F2—C141.340 (4)C7—C81.372 (3)
O1—C21.218 (3)C7—H70.9300
O2—C41.358 (2)C8—H80.9300
O2—C91.426 (3)C9—C101.489 (3)
C1—C21.480 (3)C9—H9A0.9700
C1—H1A0.9600C9—H9B0.9700
C1—H1B0.9600C10—C111.365 (3)
C1—H1C0.9600C10—C151.368 (4)
C2—C31.491 (3)C11—C121.361 (4)
C3—C81.389 (3)C11—H110.9300
C3—C41.404 (3)C12—C131.336 (4)
C4—C51.390 (3)C13—C141.342 (5)
C5—C61.371 (3)C13—H130.9300
C5—H50.9300C14—C151.384 (4)
C6—C71.365 (3)C15—H150.9300
C4—O2—C9118.86 (17)C7—C8—H8118.6
C2—C1—H1A109.5C3—C8—H8118.6
C2—C1—H1B109.5O2—C9—C10106.94 (18)
H1A—C1—H1B109.5O2—C9—H9A110.3
C2—C1—H1C109.5C10—C9—H9A110.3
H1A—C1—H1C109.5O2—C9—H9B110.3
H1B—C1—H1C109.5C10—C9—H9B110.3
O1—C2—C1119.4 (2)H9A—C9—H9B108.6
O1—C2—C3118.1 (2)C11—C10—C15118.4 (2)
C1—C2—C3122.6 (2)C11—C10—C9119.5 (2)
C8—C3—C4116.9 (2)C15—C10—C9122.0 (3)
C8—C3—C2117.04 (19)C12—C11—C10119.4 (3)
C4—C3—C2126.04 (19)C12—C11—H11120.3
O2—C4—C5122.9 (2)C10—C11—H11120.3
O2—C4—C3116.96 (18)C13—C12—F1118.0 (3)
C5—C4—C3120.2 (2)C13—C12—C11123.8 (3)
C6—C5—C4120.2 (2)F1—C12—C11118.2 (3)
C6—C5—H5119.9C12—C13—C14116.5 (3)
C4—C5—H5119.9C12—C13—H13121.7
C7—C6—C5120.9 (2)C14—C13—H13121.7
C7—C6—H6119.6F2—C14—C13118.8 (3)
C5—C6—H6119.6F2—C14—C15118.6 (4)
C6—C7—C8118.9 (2)C13—C14—C15122.6 (3)
C6—C7—H7120.5C10—C15—C14119.2 (3)
C8—C7—H7120.5C10—C15—H15120.4
C7—C8—C3122.9 (2)C14—C15—H15120.4
O1—C2—C3—C81.7 (3)C2—C3—C8—C7179.8 (2)
C1—C2—C3—C8178.3 (2)C4—O2—C9—C10173.0 (2)
O1—C2—C3—C4178.8 (2)O2—C9—C10—C11107.6 (3)
C1—C2—C3—C41.2 (3)O2—C9—C10—C1570.1 (3)
C9—O2—C4—C50.1 (3)C15—C10—C11—C120.2 (4)
C9—O2—C4—C3179.2 (2)C9—C10—C11—C12177.9 (2)
C8—C3—C4—O2178.31 (19)C10—C11—C12—C131.0 (5)
C2—C3—C4—O21.2 (3)C10—C11—C12—F1179.0 (3)
C8—C3—C4—C50.8 (3)F1—C12—C13—C14179.2 (3)
C2—C3—C4—C5179.7 (2)C11—C12—C13—C141.1 (5)
O2—C4—C5—C6178.5 (2)C12—C13—C14—F2179.7 (3)
C3—C4—C5—C60.6 (3)C12—C13—C14—C150.6 (5)
C4—C5—C6—C70.1 (4)C11—C10—C15—C140.3 (4)
C5—C6—C7—C80.1 (4)C9—C10—C15—C14177.3 (3)
C6—C7—C8—C30.2 (4)F2—C14—C15—C10179.0 (3)
C4—C3—C8—C70.6 (3)C13—C14—C15—C100.1 (5)

Experimental details

Crystal data
Chemical formulaC15H12F2O2
Mr262.25
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.2808 (7), 7.9734 (8), 11.6466 (12)
α, β, γ (°)91.587 (1), 106.559 (2), 95.343 (1)
V3)644.22 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.42 × 0.38 × 0.20
Data collection
DiffractometerBruker SMART CD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.956, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
3373, 2239, 1402
Rint0.014
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.153, 1.03
No. of reflections2239
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.20

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We would like to acknowledge funding support from the National Natural Science Foundation of China (grant No. 30971882) and the Program of Natural Science Basic Research in Shaanxi (No. 2009JM3010).

References

First citationBruker (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDermer, O. C. (1934). Chem. Rev. 14, 385–430.  CrossRef CAS Google Scholar
First citationMa, Y.-T., Wang, J.-J., Liu, X.-W., Yang, S.-X. & Gao, J.-M. (2010). Acta Cryst. E66, o52.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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