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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Dec 17;65(Pt 1):o150. doi: 10.1107/S1600536808042372

3-(4-tert-Butyl­phen­yl)-1-(4-fluoro­phen­yl)-3-hydroxy­prop-2-en-1-one

Chunyang Zheng a,*, Dunjia Wang b, Ling Fan b
PMCID: PMC2968064  PMID: 21581608

Abstract

The title mol­ecule, C19H19FO2, exits in the enol form with a dihedral angle of 33.06 (8)° between the two benzene rings. The mol­ecular conformation is stabilized in part by an intra­molecular O—H⋯O hydrogen bond.

Related literature

For background information on 1,3-diketones, see: Baskar & Roesky (2005 ▶); Bassett et al. (2004 ▶); Bertolasi et al. (1991 ▶); Jang et al. (2006 ▶); Soldatov et al. (2003 ▶); Vila et al. (1991 ▶).graphic file with name e-65-0o150-scheme1.jpg

Experimental

Crystal data

  • C19H19FO2

  • M r = 298.34

  • Monoclinic, Inline graphic

  • a = 9.8349 (12) Å

  • b = 10.0163 (13) Å

  • c = 16.232 (2) Å

  • β = 97.788 (2)°

  • V = 1584.3 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 (2) K

  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.993, T max = 0.995

  • 12039 measured reflections

  • 3099 independent reflections

  • 2199 reflections with I > 2σ(I)

  • R int = 0.074

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050

  • wR(F 2) = 0.131

  • S = 1.00

  • 3099 reflections

  • 205 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042372/lh2743sup1.cif

e-65-0o150-sup1.cif (19.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042372/lh2743Isup2.hkl

e-65-0o150-Isup2.hkl (152.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2A⋯O1 1.16 (2) 1.38 (2) 2.4720 (16) 154 (2)
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Acknowledgments

The authors are grateful to Hubei Normal University for financial support.

supplementary crystallographic information

Comment

1,3-Diketones are interesting due to their enolic tautomeric forms and their ability to form strong intermolecular or intramolecular hydrogen bonds (Bertolasi et al., 1991; Vila et al., 1991). They are used widely in the chemistry of metallocomplexes (Baskar et al., 2005; Bassett et al., 2004; Jang et al., 2006; Soldatov et al., 2003). The title compound (I) (Fig. 1), is in the enol form stabilized by an intramolecular O-H···O hydrogen bond (see Table 1).

Experimental

1-(4-fluorophenyl)ethanone (1.38 g, 0.01 mol), methyl 4-tert-butylbenzoate (1.92 g, 0.01 mol), NaNH2 (0.78 g, 0.02 mol) and dry ether (60 ml) were placed into round bottom flask. The mixture was stirred for 6 h at room temperature under a blanket of nitrogen, acidified with dilute hydrochloric acid, and stirring was continued until all solids dissolved. The ether layer was separated and washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4 and was removed by evaporation. The residual solid was recrystallized from ethanol solution to give the title compound (I) (yield 1.78 g, 59.6%, m.p. 388 K). Crystals suitable for X-ray diffraction were grown by slow evaporation of a CHCl3—EtOH (1:4) solution of the title compound at room temperature.

Refinement

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93 to 0.96 Å, and with Uiso(H) = 1.2 Ueq(C). The H atom of the hydroxyl group was located in a difference Fourier map and its position was refined freely, with Uiso(H) = 1.5 Uiso(O).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a intramolecular hydrogen bond.

Crystal data

C19H19FO2 F(000) = 632
Mr = 298.34 Dx = 1.251 Mg m−3
Monoclinic, P21/n Melting point: 388 K
Hall symbol: -P 2yn Mo Kα radiation, λ = 0.71073 Å
a = 9.8349 (12) Å Cell parameters from 3223 reflections
b = 10.0163 (13) Å θ = 2.3–22.9°
c = 16.232 (2) Å µ = 0.09 mm−1
β = 97.788 (2)° T = 298 K
V = 1584.3 (3) Å3 Block, colorless
Z = 4 0.20 × 0.10 × 0.10 mm
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Data collection

Bruker SMART CCD diffractometer 3099 independent reflections
Radiation source: fine-focus sealed tube 2199 reflections with I > 2σ(I)
graphite Rint = 0.074
φ and ω scans θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −11→12
Tmin = 0.993, Tmax = 0.995 k = −12→12
12039 measured reflections l = −19→19
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131 H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
3099 reflections (Δ/σ)max = 0.001
205 parameters Δρmax = 0.17 e Å−3
0 restraints Δρmin = −0.18 e Å−3
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.12996 (18) 0.09274 (19) −0.07276 (10) 0.0599 (5)
C2 0.0803 (2) 0.2198 (2) −0.08119 (10) 0.0666 (5)
H2 0.0522 0.2559 −0.1335 0.080*
C3 0.07296 (18) 0.29335 (17) −0.01033 (9) 0.0587 (5)
H3 0.0401 0.3805 −0.0150 0.070*
C4 0.11376 (15) 0.23969 (16) 0.06796 (9) 0.0457 (4)
C5 0.16498 (16) 0.11083 (17) 0.07303 (9) 0.0545 (4)
H5 0.1943 0.0741 0.1250 0.065*
C6 0.17340 (17) 0.03602 (18) 0.00290 (10) 0.0596 (5)
H6 0.2076 −0.0506 0.0068 0.071*
C7 0.09992 (16) 0.32242 (16) 0.14225 (9) 0.0491 (4)
C8 0.11727 (16) 0.27023 (16) 0.22333 (9) 0.0499 (4)
H8 0.1464 0.1824 0.2321 0.060*
C9 0.09179 (16) 0.34703 (16) 0.29012 (9) 0.0498 (4)
C10 0.09963 (16) 0.29479 (16) 0.37555 (9) 0.0475 (4)
C11 0.01481 (18) 0.34617 (16) 0.42948 (10) 0.0561 (4)
H11 −0.0459 0.4148 0.4118 0.067*
C12 0.01961 (17) 0.29659 (17) 0.50883 (10) 0.0565 (4)
H12 −0.0396 0.3319 0.5432 0.068*
C13 0.10956 (15) 0.19580 (15) 0.53959 (9) 0.0464 (4)
C14 0.19521 (17) 0.14742 (17) 0.48502 (9) 0.0557 (4)
H14 0.2580 0.0808 0.5032 0.067*
C15 0.19034 (17) 0.19472 (17) 0.40495 (9) 0.0541 (4)
H15 0.2488 0.1589 0.3702 0.065*
C16 0.11634 (16) 0.14446 (16) 0.62880 (9) 0.0512 (4)
C17 −0.02548 (19) 0.1488 (2) 0.65807 (11) 0.0744 (6)
H17A −0.0544 0.2400 0.6614 0.112*
H17B −0.0205 0.1080 0.7119 0.112*
H17C −0.0903 0.1012 0.6193 0.112*
C18 0.2134 (2) 0.2360 (2) 0.68505 (10) 0.0774 (6)
H18A 0.3020 0.2364 0.6664 0.116*
H18B 0.2221 0.2039 0.7412 0.116*
H18C 0.1770 0.3250 0.6827 0.116*
C19 0.1691 (2) 0.00150 (18) 0.63681 (12) 0.0791 (6)
H19A 0.1140 −0.0541 0.5973 0.119*
H19B 0.1639 −0.0305 0.6920 0.119*
H19C 0.2628 −0.0010 0.6262 0.119*
F1 0.13561 (14) 0.01881 (12) −0.14199 (6) 0.0933 (4)
O1 0.06597 (13) 0.44469 (12) 0.12968 (7) 0.0671 (4)
O2 0.05431 (14) 0.47163 (12) 0.27994 (8) 0.0720 (4)
H2A 0.050 (2) 0.485 (2) 0.2088 (15) 0.108*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0655 (12) 0.0679 (12) 0.0478 (9) 0.0042 (9) 0.0136 (8) −0.0004 (8)
C2 0.0872 (14) 0.0695 (13) 0.0436 (9) 0.0131 (10) 0.0110 (8) 0.0131 (8)
C3 0.0709 (12) 0.0531 (10) 0.0526 (10) 0.0069 (9) 0.0105 (8) 0.0105 (8)
C4 0.0383 (9) 0.0509 (10) 0.0480 (9) −0.0008 (7) 0.0060 (6) 0.0057 (7)
C5 0.0546 (10) 0.0619 (11) 0.0458 (9) 0.0075 (8) 0.0026 (7) 0.0083 (8)
C6 0.0628 (12) 0.0584 (11) 0.0574 (10) 0.0130 (9) 0.0080 (8) 0.0037 (8)
C7 0.0445 (9) 0.0480 (10) 0.0540 (9) −0.0026 (7) 0.0035 (7) 0.0054 (7)
C8 0.0547 (10) 0.0466 (10) 0.0475 (9) 0.0040 (8) 0.0040 (7) 0.0024 (7)
C9 0.0493 (10) 0.0455 (10) 0.0525 (9) −0.0028 (7) −0.0003 (7) −0.0013 (7)
C10 0.0484 (9) 0.0456 (9) 0.0468 (8) −0.0007 (7) 0.0004 (7) −0.0062 (7)
C11 0.0625 (11) 0.0490 (10) 0.0560 (10) 0.0152 (8) 0.0049 (8) 0.0000 (7)
C12 0.0612 (11) 0.0559 (11) 0.0537 (10) 0.0124 (9) 0.0128 (8) −0.0052 (8)
C13 0.0465 (9) 0.0443 (9) 0.0475 (8) −0.0021 (7) 0.0028 (7) −0.0069 (7)
C14 0.0547 (10) 0.0603 (11) 0.0507 (9) 0.0163 (8) 0.0017 (7) 0.0021 (7)
C15 0.0531 (10) 0.0615 (11) 0.0480 (9) 0.0132 (8) 0.0075 (7) −0.0049 (7)
C16 0.0502 (10) 0.0554 (10) 0.0471 (9) −0.0006 (8) 0.0029 (7) −0.0021 (7)
C17 0.0699 (13) 0.0938 (15) 0.0614 (11) −0.0013 (11) 0.0153 (9) 0.0105 (10)
C18 0.0857 (14) 0.0914 (15) 0.0515 (10) −0.0224 (12) −0.0039 (9) −0.0023 (9)
C19 0.1093 (17) 0.0651 (13) 0.0644 (12) 0.0161 (12) 0.0167 (11) 0.0115 (9)
F1 0.1407 (12) 0.0884 (9) 0.0527 (6) 0.0260 (7) 0.0201 (6) −0.0074 (5)
O1 0.0956 (10) 0.0484 (7) 0.0566 (7) 0.0054 (7) 0.0083 (6) 0.0085 (5)
O2 0.1083 (11) 0.0459 (7) 0.0598 (8) 0.0109 (7) 0.0044 (7) −0.0007 (5)
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Geometric parameters (Å, °)

C1—F1 1.3532 (19) C11—H11 0.9300
C1—C2 1.364 (3) C12—C13 1.390 (2)
C1—C6 1.368 (2) C12—H12 0.9300
C2—C3 1.376 (2) C13—C14 1.390 (2)
C2—H2 0.9300 C13—C16 1.530 (2)
C3—C4 1.388 (2) C14—C15 1.378 (2)
C3—H3 0.9300 C14—H14 0.9300
C4—C5 1.384 (2) C15—H15 0.9300
C4—C7 1.485 (2) C16—C19 1.523 (2)
C5—C6 1.375 (2) C16—C18 1.533 (2)
C5—H5 0.9300 C16—C17 1.534 (2)
C6—H6 0.9300 C17—H17A 0.9600
C7—O1 1.2784 (19) C17—H17B 0.9600
C7—C8 1.405 (2) C17—H17C 0.9600
C8—C9 1.380 (2) C18—H18A 0.9600
C8—H8 0.9300 C18—H18B 0.9600
C9—O2 1.3054 (19) C18—H18C 0.9600
C9—C10 1.474 (2) C19—H19A 0.9600
C10—C15 1.383 (2) C19—H19B 0.9600
C10—C11 1.387 (2) C19—H19C 0.9600
C11—C12 1.375 (2) O2—H2A 1.16 (2)
F1—C1—C2 118.81 (15) C14—C13—C12 115.83 (14)
F1—C1—C6 118.39 (16) C14—C13—C16 122.26 (14)
C2—C1—C6 122.81 (16) C12—C13—C16 121.89 (14)
C1—C2—C3 118.32 (15) C15—C14—C13 122.32 (15)
C1—C2—H2 120.8 C15—C14—H14 118.8
C3—C2—H2 120.8 C13—C14—H14 118.8
C2—C3—C4 121.11 (16) C14—C15—C10 120.86 (15)
C2—C3—H3 119.4 C14—C15—H15 119.6
C4—C3—H3 119.4 C10—C15—H15 119.6
C5—C4—C3 118.25 (14) C19—C16—C13 111.57 (14)
C5—C4—C7 123.03 (13) C19—C16—C18 109.51 (15)
C3—C4—C7 118.72 (14) C13—C16—C18 107.85 (13)
C6—C5—C4 121.43 (14) C19—C16—C17 108.31 (15)
C6—C5—H5 119.3 C13—C16—C17 111.03 (13)
C4—C5—H5 119.3 C18—C16—C17 108.51 (15)
C1—C6—C5 118.07 (16) C16—C17—H17A 109.5
C1—C6—H6 121.0 C16—C17—H17B 109.5
C5—C6—H6 121.0 H17A—C17—H17B 109.5
O1—C7—C8 120.13 (14) C16—C17—H17C 109.5
O1—C7—C4 117.12 (13) H17A—C17—H17C 109.5
C8—C7—C4 122.71 (14) H17B—C17—H17C 109.5
C9—C8—C7 121.11 (15) C16—C18—H18A 109.5
C9—C8—H8 119.4 C16—C18—H18B 109.5
C7—C8—H8 119.4 H18A—C18—H18B 109.5
O2—C9—C8 120.78 (14) C16—C18—H18C 109.5
O2—C9—C10 115.86 (14) H18A—C18—H18C 109.5
C8—C9—C10 123.32 (15) H18B—C18—H18C 109.5
C15—C10—C11 117.77 (15) C16—C19—H19A 109.5
C15—C10—C9 122.06 (14) C16—C19—H19B 109.5
C11—C10—C9 120.17 (15) H19A—C19—H19B 109.5
C12—C11—C10 120.64 (15) C16—C19—H19C 109.5
C12—C11—H11 119.7 H19A—C19—H19C 109.5
C10—C11—H11 119.7 H19B—C19—H19C 109.5
C11—C12—C13 122.56 (15) C7—O1—H2A 101.2 (10)
C11—C12—H12 118.7 C7—O1—H2A 101.2 (10)
C13—C12—H12 118.7 C9—O2—H2A 102.1 (11)
F1—C1—C2—C3 178.96 (17) O2—C9—C10—C11 29.4 (2)
C6—C1—C2—C3 −0.5 (3) C8—C9—C10—C11 −148.40 (16)
C1—C2—C3—C4 −0.5 (3) C15—C10—C11—C12 −1.3 (3)
C2—C3—C4—C5 1.3 (3) C9—C10—C11—C12 178.87 (15)
C2—C3—C4—C7 −178.35 (16) C10—C11—C12—C13 1.2 (3)
C3—C4—C5—C6 −1.2 (2) C11—C12—C13—C14 0.0 (3)
C7—C4—C5—C6 178.49 (15) C11—C12—C13—C16 178.28 (15)
F1—C1—C6—C5 −178.81 (15) C12—C13—C14—C15 −0.9 (3)
C2—C1—C6—C5 0.6 (3) C16—C13—C14—C15 −179.20 (15)
C4—C5—C6—C1 0.2 (3) C13—C14—C15—C10 0.7 (3)
C5—C4—C7—O1 172.32 (15) C11—C10—C15—C14 0.4 (3)
C3—C4—C7—O1 −8.0 (2) C9—C10—C15—C14 −179.79 (15)
C5—C4—C7—C8 −10.2 (2) C14—C13—C16—C19 −27.3 (2)
C3—C4—C7—C8 169.45 (15) C12—C13—C16—C19 154.50 (16)
O1—C7—C8—C9 3.2 (2) C14—C13—C16—C18 93.01 (19)
C4—C7—C8—C9 −174.20 (14) C12—C13—C16—C18 −85.19 (19)
C7—C8—C9—O2 −1.8 (2) C14—C13—C16—C17 −148.23 (16)
C7—C8—C9—C10 175.89 (14) C12—C13—C16—C17 33.6 (2)
O2—C9—C10—C15 −150.37 (16) C8—C7—O1—H2A −3.3 (9)
C8—C9—C10—C15 31.8 (2) C4—C7—O1—H2A 174.2 (9)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O2—H2A···O1 1.16 (2) 1.38 (2) 2.4720 (16) 154 (2)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2743).

References

  1. Baskar, V. & Roesky, P. W. (2005). Z. Anorg. Allg. Chem.631, 2782–2785.
  2. Bassett, A. P., Magennis, S. W., Glover, P. B., Lewis, D. J., Spencer, N., Parsons, S., Williams, R. M., Cola, L. D. & Pikramenou, Z. (2004). J. Am. Chem. Soc.126, 9413–9424. [DOI] [PubMed]
  3. Bertolasi, V., Cilli, P., Ferretti, V. & Gilli, G. (1991). J. Am. Chem. Soc.113, 4917–4925.
  4. Bruker (1997). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  5. Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  6. Jang, H., Shin, C. H., Jung, B. J., Kim, D. H., Shim, H. K. & Do, Y. (2006). Eur. J. Inorg. Chem.4, 718–725.
  7. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  8. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  9. Soldatov, D. V., Zanina, A. S., Enright, G. D., Ratcliffe, C. I. & Ripmeester, J. A. (2003). Cryst. Growth & Des.3, 1005–1013.
  10. Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  11. Vila, A. J., Lagier, C. M. & Olivieri, A. C. (1991). J. Phys. Chem.95, 5069–5073.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042372/lh2743sup1.cif

e-65-0o150-sup1.cif (19.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042372/lh2743Isup2.hkl

e-65-0o150-Isup2.hkl (152.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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