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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Nov 13;64(Pt 12):o2326. doi: 10.1107/S1600536808036659

3-[4-(Benz­yloxy)phen­yl]-1-(2-fur­yl)-3-hydroxy­prop-2-en-1-one

Chun-Yang Zheng a,*, Dun-Jia Wang b, Ling Fan b
PMCID: PMC2959881  PMID: 21581301

Abstract

In the crystal structure of the title compound, C20H16O4, which is in the enol form, the central benzene ring makes dihedral angles of 63.42 (9) and 5.19 (10)° with the phenyl and furan rings, respectively. There is a short strong intra­molecular O—H⋯O hydrogen bond.

Related literature

For hydrogen bonds in 1,3-diketones, see: Bertolasi et al. (1991 ▶); Gilli et al. (2004 ▶); Vila et al. (1991 ▶). For 1,3-diketones as ligands, see: Baskar & Roesky (2005 ▶); Bassett et al. (2004 ▶); Jang et al. (2006 ▶); Soldatov et al. (2003 ▶).graphic file with name e-64-o2326-scheme1.jpg

Experimental

Crystal data

  • C20H16O4

  • M r = 320.33

  • Triclinic, Inline graphic

  • a = 5.8927 (6) Å

  • b = 11.3365 (11) Å

  • c = 13.3039 (13) Å

  • α = 112.111 (3)°

  • β = 96.687 (3)°

  • γ = 98.638 (3)°

  • V = 799.39 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 (2) K

  • 0.32 × 0.20 × 0.12 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.983

  • 6611 measured reflections

  • 3439 independent reflections

  • 2268 reflections with I > 2σ(I)

  • R int = 0.078

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056

  • wR(F 2) = 0.147

  • S = 0.95

  • 3439 reflections

  • 220 parameters

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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.29 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036659/is2357sup1.cif

e-64-o2326-sup1.cif (19KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036659/is2357Isup2.hkl

e-64-o2326-Isup2.hkl (168.6KB, 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⋯O3 1.15 (3) 1.38 (3) 2.5030 (16) 162 (2)
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Acknowledgments

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

supplementary crystallographic information

Comment

1,3-Diketones in their enolic tautomeric forms have been extensively studied owing to their ability to form strong intermolecular or intramolecular hydrogen bonds (Vila et al., 1991; Bertolasi et al., 1991; Gilli et al., 2004). They are among the most studied ligands in the chemistry of metal complexes and used widely in the chemistry of metallocomplexes (Baskar & Roesky, 2005; Bassett et al., 2004; Jang et al., 2006; Soldatov et al., 2003).

The crystal structure of the title compound, (I), is in the enol form stabilized by an intramolecular hydrogen bond (Fig. 1). The distances of O2—H2 and O3···H2 are 1.15 (3) and 1.38 (3) Å, respectively. The central benzene ring (C8—C13) makes dihedral angles of 63.42 and 5.19° with two aromatic rings (C1—C6) and (C17—O4), respectively. The crystal packing is stabilized by van der Waals forces.

Experimental

1-[4-(Benzyloxy)phenyl]ethanone (2.26 g, 0.01 mol), methyl furan-2-carboxylate (1.26 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 an ethanol solution to give the title compound (I) (yield 1.75 g, 54.7%; m.p. 403 K). Crystals suitable for X-ray diffraction were grown by slow evaporation of a CH2Cl2—EtOH (1:4) solution 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 0.97 Å, and with Uiso(H) = 1.2Ueq(C). The H atom of the hydroxyl group was located in a difference Fourier map and its position was refined freely, with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.

Fig. 1.

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View of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates an intramolecular hydrogen bond.

Crystal data

C20H16O4 Z = 2
Mr = 320.33 F000 = 336
Triclinic, P1 Dx = 1.331 Mg m−3
Hall symbol: -P 1 Melting point: 403 K
a = 5.8927 (6) Å Mo Kα radiation λ = 0.71073 Å
b = 11.3365 (11) Å Cell parameters from 1997 reflections
c = 13.3039 (13) Å θ = 3.1–26.1º
α = 112.111 (3)º µ = 0.09 mm−1
β = 96.687 (3)º T = 298 (2) K
γ = 98.638 (3)º Block, yellow
V = 799.39 (14) Å3 0.32 × 0.20 × 0.12 mm
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Data collection

Bruker SMART APEX CCD area-detector diffractometer 3439 independent reflections
Radiation source: fine-focus sealed tube 2268 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.078
T = 298(2) K θmax = 27.0º
φ and ω scans θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996) h = −7→7
Tmin = 0.978, Tmax = 0.983 k = −14→14
6611 measured reflections l = −16→16
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147   w = 1/[σ2(Fo2) + (0.0676P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95 (Δ/σ)max < 0.001
3439 reflections Δρmax = 0.18 e Å−3
220 parameters Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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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 −0.1919 (3) 0.94140 (17) −0.21175 (14) 0.0561 (4)
H1 −0.2852 0.9490 −0.1588 0.067*
C2 −0.2151 (3) 1.01001 (18) −0.27760 (15) 0.0624 (5)
H2 −0.3229 1.0636 −0.2686 0.075*
C3 −0.0791 (3) 0.99904 (18) −0.35624 (13) 0.0628 (5)
H3 −0.0943 1.0449 −0.4008 0.075*
C4 0.0791 (4) 0.9200 (2) −0.36863 (14) 0.0707 (5)
H4 0.1716 0.9124 −0.4219 0.085*
C5 0.1021 (3) 0.85205 (18) −0.30303 (14) 0.0625 (5)
H5 0.2100 0.7986 −0.3124 0.075*
C6 −0.0332 (3) 0.86224 (15) −0.22321 (12) 0.0470 (4)
C7 −0.0042 (3) 0.78860 (17) −0.15223 (14) 0.0543 (4)
H7A −0.1266 0.7946 −0.1088 0.065*
H7B −0.0133 0.6975 −0.1976 0.065*
C8 0.2985 (3) 0.78337 (14) −0.01798 (12) 0.0437 (4)
C9 0.1650 (3) 0.67956 (17) −0.00705 (15) 0.0572 (5)
H9 0.0099 0.6479 −0.0432 0.069*
C10 0.2624 (3) 0.62314 (17) 0.05756 (14) 0.0566 (5)
H10 0.1708 0.5530 0.0641 0.068*
C11 0.4923 (3) 0.66708 (14) 0.11326 (12) 0.0430 (4)
C12 0.6215 (3) 0.77425 (15) 0.10371 (12) 0.0487 (4)
H12 0.7755 0.8073 0.1413 0.058*
C13 0.5265 (3) 0.83230 (15) 0.04000 (13) 0.0493 (4)
H13 0.6155 0.9047 0.0357 0.059*
C14 0.5877 (3) 0.60034 (15) 0.17882 (12) 0.0459 (4)
C15 0.8145 (3) 0.63971 (16) 0.23933 (13) 0.0493 (4)
H15 0.9149 0.7099 0.2370 0.059*
C16 0.8939 (3) 0.57587 (17) 0.30329 (13) 0.0523 (4)
C17 1.1263 (3) 0.62181 (18) 0.37217 (13) 0.0561 (4)
C18 1.2389 (4) 0.5838 (2) 0.44496 (16) 0.0779 (6)
H18 1.1821 0.5149 0.4632 0.094*
C19 1.4595 (4) 0.6689 (3) 0.48793 (17) 0.0878 (7)
H19 1.5767 0.6671 0.5402 0.105*
C20 1.4681 (4) 0.7517 (2) 0.43989 (17) 0.0821 (7)
H20 1.5957 0.8185 0.4537 0.099*
O1 0.22079 (19) 0.84506 (10) −0.08083 (9) 0.0549 (3)
O2 0.4480 (2) 0.49997 (11) 0.17879 (10) 0.0593 (3)
O3 0.7661 (2) 0.47547 (13) 0.30691 (11) 0.0682 (4)
O4 1.2673 (2) 0.72692 (13) 0.36792 (9) 0.0661 (4)
H2A 0.573 (4) 0.473 (2) 0.2360 (18) 0.099*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0612 (10) 0.0584 (11) 0.0545 (10) 0.0197 (8) 0.0132 (8) 0.0256 (9)
C2 0.0691 (11) 0.0551 (11) 0.0649 (11) 0.0249 (9) 0.0015 (9) 0.0249 (9)
C3 0.0835 (13) 0.0586 (11) 0.0460 (10) 0.0101 (10) −0.0026 (9) 0.0268 (9)
C4 0.0881 (13) 0.0858 (15) 0.0494 (10) 0.0291 (11) 0.0207 (10) 0.0330 (10)
C5 0.0706 (11) 0.0704 (12) 0.0559 (10) 0.0315 (9) 0.0166 (9) 0.0281 (9)
C6 0.0533 (9) 0.0446 (9) 0.0408 (8) 0.0094 (7) 0.0023 (7) 0.0167 (7)
C7 0.0536 (9) 0.0518 (10) 0.0594 (10) 0.0085 (7) 0.0032 (8) 0.0277 (8)
C8 0.0538 (9) 0.0380 (8) 0.0411 (8) 0.0099 (7) 0.0076 (7) 0.0181 (7)
C9 0.0489 (9) 0.0528 (10) 0.0709 (11) −0.0024 (7) −0.0039 (8) 0.0354 (9)
C10 0.0540 (10) 0.0505 (10) 0.0702 (11) −0.0013 (8) 0.0000 (8) 0.0375 (9)
C11 0.0491 (8) 0.0407 (8) 0.0413 (8) 0.0096 (7) 0.0095 (7) 0.0183 (7)
C12 0.0481 (9) 0.0494 (9) 0.0481 (9) 0.0015 (7) 0.0031 (7) 0.0239 (8)
C13 0.0536 (9) 0.0434 (9) 0.0515 (9) −0.0011 (7) 0.0056 (7) 0.0251 (8)
C14 0.0568 (9) 0.0432 (9) 0.0421 (8) 0.0121 (7) 0.0144 (7) 0.0198 (7)
C15 0.0556 (9) 0.0494 (9) 0.0468 (9) 0.0114 (7) 0.0077 (7) 0.0239 (8)
C16 0.0633 (10) 0.0554 (11) 0.0463 (9) 0.0246 (8) 0.0171 (8) 0.0230 (8)
C17 0.0650 (10) 0.0659 (12) 0.0482 (10) 0.0312 (9) 0.0164 (8) 0.0267 (9)
C18 0.0854 (15) 0.1060 (17) 0.0697 (12) 0.0522 (13) 0.0222 (11) 0.0510 (12)
C19 0.0787 (15) 0.128 (2) 0.0584 (13) 0.0552 (14) 0.0019 (10) 0.0304 (13)
C20 0.0648 (12) 0.0965 (17) 0.0662 (13) 0.0287 (11) −0.0040 (10) 0.0124 (12)
O1 0.0627 (7) 0.0467 (7) 0.0560 (7) 0.0009 (5) −0.0054 (5) 0.0302 (6)
O2 0.0605 (7) 0.0568 (7) 0.0712 (8) 0.0060 (6) 0.0086 (6) 0.0408 (7)
O3 0.0772 (9) 0.0687 (9) 0.0799 (9) 0.0223 (7) 0.0166 (7) 0.0498 (7)
O4 0.0671 (8) 0.0683 (9) 0.0576 (8) 0.0189 (7) 0.0014 (6) 0.0208 (7)
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Geometric parameters (Å, °)

C1—C6 1.373 (2) C10—H10 0.9300
C1—C2 1.381 (2) C11—C12 1.390 (2)
C1—H1 0.9300 C11—C14 1.469 (2)
C2—C3 1.371 (3) C12—C13 1.373 (2)
C2—H2 0.9300 C12—H12 0.9300
C3—C4 1.369 (3) C13—H13 0.9300
C3—H3 0.9300 C14—O2 1.3000 (19)
C4—C5 1.373 (2) C14—C15 1.391 (2)
C4—H4 0.9300 C15—C16 1.393 (2)
C5—C6 1.382 (2) C15—H15 0.9300
C5—H5 0.9300 C16—O3 1.287 (2)
C6—C7 1.489 (2) C16—C17 1.456 (3)
C7—O1 1.4364 (19) C17—C18 1.347 (2)
C7—H7A 0.9700 C17—O4 1.371 (2)
C7—H7B 0.9700 C18—C19 1.408 (3)
C8—O1 1.3583 (17) C18—H18 0.9300
C8—C9 1.379 (2) C19—C20 1.318 (3)
C8—C13 1.386 (2) C19—H19 0.9300
C9—C10 1.374 (2) C20—O4 1.352 (2)
C9—H9 0.9300 C20—H20 0.9300
C10—C11 1.385 (2) O2—H2A 1.15 (3)
C6—C1—C2 121.06 (16) C10—C11—C14 119.56 (13)
C6—C1—H1 119.5 C12—C11—C14 123.34 (14)
C2—C1—H1 119.5 C13—C12—C11 121.39 (14)
C3—C2—C1 119.91 (17) C13—C12—H12 119.3
C3—C2—H2 120.0 C11—C12—H12 119.3
C1—C2—H2 120.0 C12—C13—C8 120.24 (14)
C4—C3—C2 119.52 (16) C12—C13—H13 119.9
C4—C3—H3 120.2 C8—C13—H13 119.9
C2—C3—H3 120.2 O2—C14—C15 119.95 (14)
C3—C4—C5 120.50 (17) O2—C14—C11 116.68 (14)
C3—C4—H4 119.8 C15—C14—C11 123.37 (14)
C5—C4—H4 119.8 C14—C15—C16 121.14 (15)
C4—C5—C6 120.71 (17) C14—C15—H15 119.4
C4—C5—H5 119.6 C16—C15—H15 119.4
C6—C5—H5 119.6 O3—C16—C15 122.40 (16)
C1—C6—C5 118.30 (15) O3—C16—C17 116.31 (15)
C1—C6—C7 121.80 (15) C15—C16—C17 121.28 (16)
C5—C6—C7 119.90 (15) C18—C17—O4 109.43 (17)
O1—C7—C6 107.58 (12) C18—C17—C16 133.19 (19)
O1—C7—H7A 110.2 O4—C17—C16 117.37 (14)
C6—C7—H7A 110.2 C17—C18—C19 106.5 (2)
O1—C7—H7B 110.2 C17—C18—H18 126.7
C6—C7—H7B 110.2 C19—C18—H18 126.7
H7A—C7—H7B 108.5 C20—C19—C18 106.89 (19)
O1—C8—C9 124.48 (14) C20—C19—H19 126.6
O1—C8—C13 116.21 (13) C18—C19—H19 126.6
C9—C8—C13 119.29 (14) C19—C20—O4 111.2 (2)
C10—C9—C8 119.65 (15) C19—C20—H20 124.4
C10—C9—H9 120.2 O4—C20—H20 124.4
C8—C9—H9 120.2 C8—O1—C7 118.05 (11)
C9—C10—C11 122.26 (15) C14—O2—H2A 99.0 (11)
C9—C10—H10 118.9 C16—O3—H2A 95.5 (9)
C11—C10—H10 118.9 C20—O4—C17 105.94 (16)
C10—C11—C12 117.10 (14)
C6—C1—C2—C3 0.3 (3) C12—C11—C14—O2 −178.85 (14)
C1—C2—C3—C4 −0.1 (3) C10—C11—C14—C15 −178.45 (15)
C2—C3—C4—C5 0.0 (3) C12—C11—C14—C15 1.4 (2)
C3—C4—C5—C6 −0.1 (3) O2—C14—C15—C16 −2.1 (2)
C2—C1—C6—C5 −0.4 (2) C11—C14—C15—C16 177.71 (14)
C2—C1—C6—C7 179.38 (15) C14—C15—C16—O3 2.4 (2)
C4—C5—C6—C1 0.4 (3) C14—C15—C16—C17 −176.10 (14)
C4—C5—C6—C7 −179.47 (17) O3—C16—C17—C18 −3.0 (3)
C1—C6—C7—O1 −111.01 (17) C15—C16—C17—C18 175.63 (18)
C5—C6—C7—O1 68.82 (19) O3—C16—C17—O4 178.65 (13)
O1—C8—C9—C10 179.06 (15) C15—C16—C17—O4 −2.7 (2)
C13—C8—C9—C10 −2.5 (3) O4—C17—C18—C19 0.0 (2)
C8—C9—C10—C11 0.2 (3) C16—C17—C18—C19 −178.42 (17)
C9—C10—C11—C12 1.7 (3) C17—C18—C19—C20 0.0 (2)
C9—C10—C11—C14 −178.47 (15) C18—C19—C20—O4 0.0 (2)
C10—C11—C12—C13 −1.3 (2) C9—C8—O1—C7 −8.7 (2)
C14—C11—C12—C13 178.88 (14) C13—C8—O1—C7 172.83 (13)
C11—C12—C13—C8 −1.0 (2) C6—C7—O1—C8 −171.88 (13)
O1—C8—C13—C12 −178.53 (13) C19—C20—O4—C17 0.0 (2)
C9—C8—C13—C12 2.9 (2) C18—C17—O4—C20 −0.02 (19)
C10—C11—C14—O2 1.3 (2) C16—C17—O4—C20 178.72 (15)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O2—H2A···O3 1.15 (3) 1.38 (3) 2.5030 (16) 162 (2)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2357).

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. Gilli, P., Bertolasi, V., Pretto, L., Ferretti, V. & Gilli, G. (2004). J. Am. Chem. Soc.126, 3845–3855. [DOI] [PubMed]
  7. Jang, H., Shin, C.-H., Jung, B.-J., Kim, D.-H., Shim, H.-K. & Do, Y. (2006). Eur. J. Inorg. Chem.4, 718–725.
  8. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  9. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  10. Soldatov, D. V., Zanina, A. S., Enright, G. D., Ratcliffe, C. I. & Ripmeester, J. A. (2003). Cryst. Growth Des.3, 1005–1013.
  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/S1600536808036659/is2357sup1.cif

e-64-o2326-sup1.cif (19KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036659/is2357Isup2.hkl

e-64-o2326-Isup2.hkl (168.6KB, 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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