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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1402.
Published online 2009 May 29. doi:  10.1107/S1600536809018121
PMCID: PMC2969700

3-(4-Fluoro­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

Abstract

The title compound, C16H13FO2, was prepared from 4-methoxy­hypnone and 4-fluoro­benzophenone by Claisen–Schmidt condensation. All the bond lengths and bond angles are in normal ranges. The dihedral angle formed by the two benzene rings is 33.49 (2)°. The crystal packing is stabilized by inter­molecular C—H(...)O hydrogen-bonding inter­actions.

Related literature

For the biological activity of chalcones, see: Hsieh et al. (1998 [triangle]); Anto et al. (1994 [triangle]). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000 [triangle]); Dimmock et al. (1998 [triangle]). For a related structure, see: Guo et al. (2008 [triangle]).

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Object name is e-65-o1402-scheme1.jpg

Experimental

Crystal data

  • C16H13FO2
  • M r = 256.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1402-efi1.jpg
  • a = 7.457 (4) Å
  • b = 11.072 (6) Å
  • c = 31.063 (18) Å
  • V = 2565 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 273 K
  • 0.13 × 0.12 × 0.09 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 14904 measured reflections
  • 3050 independent reflections
  • 2203 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.116
  • S = 1.01
  • 3050 reflections
  • 173 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018121/at2773sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018121/at2773Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of Shandong (Y2007B14; Y2008B29) and Weifang University for research grants.

supplementary crystallographic information

Comment

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al., 1998) and antioxidant (Anto et al., 1994). Of particular interest, the effectiveness of chalcones againist cancer has been investigated (De Vincenzo et al., 2000; Dimmock et al., 1998). As part of our search for new biologically active compounds we synthesized the title compound (I) and report its crystal structure here.

In the crystal structure of compound (I) (Fig. 1), the dihedral angle formed by the benzene rings (C1–C6) and (C7–C12) is 33.49 (2)°. All the bond lengths and bond angles are in normal ranges. (Guo et al., 2008). There are intra- and intermolecular C—H···O hydrogen-bond interactions to stabilize the crystal structure (Table 1, Fig. 2).

Experimental

A mixture of the 4-methoxyhypnone (0.02 mol), 4-fluorobenzophenone (0.02 mol) and 10% NaOH (10 ml) was stirred in ethanol (30 ml) for 3 h to afford the title compound (yield 83%). Single crystals suitable for X-ray measurements were obtailed by recrystallization from ethanol at room temperature.

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.96 Å, respectively, and with Uiso(H) = 1.2 or 1.5Ueq of the parent atoms.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
The packing and the hydrogen bonding interactions of (I),viewed down a axis.

Crystal data

C16H13FO2F(000) = 1072
Mr = 256.26Dx = 1.327 Mg m3Dm = 1.327 Mg m3Dm measured by not measured
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4576 reflections
a = 7.457 (4) Åθ = 2.6–27.2°
b = 11.072 (6) ŵ = 0.10 mm1
c = 31.063 (18) ÅT = 273 K
V = 2565 (3) Å3Bar, yellow
Z = 80.13 × 0.12 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer2203 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
graphiteθmax = 28.1°, θmin = 2.6°
[var phi] and ω scansh = −8→9
14904 measured reflectionsk = −14→14
3050 independent reflectionsl = −31→40

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.116w = 1/[σ2(Fo2) + (0.0529P)2 + 0.3952P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3050 reflectionsΔρmax = 0.17 e Å3
173 parametersΔρmin = −0.12 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0151 (14)

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.

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

xyzUiso*/Ueq
O20.19197 (16)0.39463 (9)0.32285 (3)0.0679 (3)
O10.09858 (15)0.57395 (10)0.13185 (3)0.0674 (3)
C160.15026 (17)0.49647 (12)0.31027 (4)0.0497 (3)
C90.13654 (16)0.52293 (11)0.26375 (4)0.0447 (3)
C150.06589 (19)0.56911 (13)0.38189 (5)0.0567 (4)
H15A0.06890.48830.39000.068*
C100.07845 (18)0.63325 (11)0.24765 (4)0.0484 (3)
H10A0.04850.69450.26680.058*
C120.10839 (18)0.56345 (12)0.17528 (4)0.0504 (3)
F−0.15021 (16)0.89082 (12)0.50973 (3)0.1015 (4)
C140.10856 (19)0.59300 (12)0.34157 (4)0.0535 (3)
H14A0.11250.67310.33260.064*
C110.06382 (18)0.65460 (12)0.20395 (4)0.0498 (3)
H11A0.02460.72920.19390.060*
C40.0339 (2)0.77956 (13)0.41030 (4)0.0578 (4)
H4A0.08540.80980.38520.069*
C80.17978 (19)0.43239 (12)0.23404 (5)0.0550 (4)
H8A0.21850.35750.24390.066*
C70.1660 (2)0.45230 (13)0.19088 (5)0.0600 (4)
H7A0.19530.39100.17170.072*
C30.01471 (18)0.65509 (13)0.41510 (4)0.0533 (3)
C5−0.0214 (2)0.85891 (16)0.44174 (5)0.0668 (4)
H5A−0.00840.94180.43810.080*
C6−0.0961 (2)0.81261 (18)0.47852 (5)0.0702 (4)
C2−0.0617 (2)0.61339 (16)0.45340 (5)0.0682 (4)
H2A−0.07530.53070.45760.082*
C130.0497 (2)0.68788 (15)0.11415 (5)0.0679 (4)
H13A0.04690.68220.08330.102*
H13B0.13600.74770.12260.102*
H13C−0.06670.71060.12460.102*
C1−0.1175 (2)0.69190 (19)0.48511 (5)0.0755 (5)
H1A−0.16860.66310.51040.091*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0827 (8)0.0466 (6)0.0744 (7)0.0011 (5)−0.0083 (6)0.0087 (5)
O10.0825 (8)0.0703 (7)0.0494 (6)0.0061 (6)−0.0002 (5)−0.0128 (5)
C160.0457 (7)0.0435 (7)0.0600 (8)−0.0068 (5)−0.0021 (6)0.0038 (6)
C90.0386 (6)0.0389 (6)0.0567 (7)−0.0051 (5)0.0001 (5)−0.0038 (5)
C150.0590 (8)0.0532 (8)0.0578 (8)−0.0064 (6)−0.0015 (6)0.0086 (6)
C100.0546 (7)0.0400 (6)0.0504 (7)−0.0005 (5)0.0041 (6)−0.0071 (5)
C120.0474 (7)0.0532 (8)0.0508 (7)−0.0031 (6)0.0009 (6)−0.0102 (6)
F0.1113 (9)0.1308 (10)0.0624 (6)0.0123 (7)0.0144 (6)−0.0209 (6)
C140.0613 (8)0.0466 (7)0.0525 (8)−0.0033 (6)−0.0038 (6)0.0037 (6)
C110.0551 (8)0.0425 (7)0.0516 (7)0.0011 (6)0.0011 (6)−0.0035 (5)
C40.0687 (9)0.0642 (9)0.0407 (7)−0.0032 (7)−0.0014 (6)0.0075 (6)
C80.0549 (8)0.0407 (7)0.0693 (9)0.0032 (6)−0.0018 (6)−0.0069 (6)
C70.0638 (9)0.0497 (8)0.0665 (9)0.0064 (6)0.0020 (7)−0.0202 (7)
C30.0531 (7)0.0624 (9)0.0443 (7)−0.0044 (6)−0.0045 (6)0.0098 (6)
C50.0815 (11)0.0689 (10)0.0501 (8)0.0018 (8)−0.0055 (7)0.0013 (7)
C60.0671 (10)0.0968 (13)0.0467 (8)0.0076 (9)−0.0016 (7)−0.0049 (8)
C20.0699 (10)0.0777 (10)0.0571 (9)−0.0075 (8)0.0018 (7)0.0184 (8)
C130.0723 (10)0.0804 (11)0.0508 (8)−0.0039 (8)0.0007 (7)−0.0011 (7)
C10.0704 (10)0.1107 (15)0.0454 (8)−0.0035 (10)0.0081 (7)0.0135 (9)

Geometric parameters (Å, °)

O2—C161.2334 (17)C4—C51.377 (2)
O1—C121.3561 (18)C4—C31.394 (2)
O1—C131.424 (2)C4—H4A0.9300
C16—C91.478 (2)C8—C71.363 (2)
C16—C141.478 (2)C8—H8A0.9300
C9—C101.3892 (19)C7—H7A0.9300
C9—C81.4002 (19)C3—C21.398 (2)
C15—C141.319 (2)C5—C61.371 (2)
C15—C31.455 (2)C5—H5A0.9300
C15—H15A0.9300C6—C11.362 (3)
C10—C111.382 (2)C2—C11.378 (3)
C10—H10A0.9300C2—H2A0.9300
C12—C111.3864 (19)C13—H13A0.9600
C12—C71.391 (2)C13—H13B0.9600
F—C61.361 (2)C13—H13C0.9600
C14—H14A0.9300C1—H1A0.9300
C11—H11A0.9300
C12—O1—C13118.30 (11)C7—C8—H8A119.5
O2—C16—C9120.57 (12)C9—C8—H8A119.5
O2—C16—C14120.38 (13)C8—C7—C12120.62 (12)
C9—C16—C14119.03 (12)C8—C7—H7A119.7
C10—C9—C8117.65 (13)C12—C7—H7A119.7
C10—C9—C16123.23 (12)C4—C3—C2117.37 (14)
C8—C9—C16119.11 (12)C4—C3—C15122.98 (12)
C14—C15—C3127.26 (14)C2—C3—C15119.63 (14)
C14—C15—H15A116.4C6—C5—C4118.32 (16)
C3—C15—H15A116.4C6—C5—H5A120.8
C11—C10—C9121.91 (12)C4—C5—H5A120.8
C11—C10—H10A119.0F—C6—C1118.87 (15)
C9—C10—H10A119.0F—C6—C5118.44 (18)
O1—C12—C11124.31 (13)C1—C6—C5122.70 (16)
O1—C12—C7116.05 (12)C1—C2—C3121.55 (16)
C11—C12—C7119.64 (13)C1—C2—H2A119.2
C15—C14—C16122.03 (13)C3—C2—H2A119.2
C15—C14—H14A119.0O1—C13—H13A109.5
C16—C14—H14A119.0O1—C13—H13B109.5
C10—C11—C12119.17 (13)H13A—C13—H13B109.5
C10—C11—H11A120.4O1—C13—H13C109.5
C12—C11—H11A120.4H13A—C13—H13C109.5
C5—C4—C3121.62 (14)H13B—C13—H13C109.5
C5—C4—H4A119.2C6—C1—C2118.45 (15)
C3—C4—H4A119.2C6—C1—H1A120.8
C7—C8—C9121.01 (13)C2—C1—H1A120.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11A···O2i0.932.503.376 (2)158
C15—H15A···O20.932.502.825 (2)101

Symmetry codes: (i) −x, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2773).

References

  • Anto, R. J., Kuttan, G., Kuttan, R., Sathyanarayana, K. & Rao, M. N. A. (1994). J. Clin. Biochem. Nutr.17, 73–80.
  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • De Vincenzo, R., Ferlini, C., Distefano, M., Gaggini, C., Riva, A., Bombardelli, E., Morazzoni, P., Valenti, P., Belluti, F., Ranelletti, F. O., Mancuso, S. & Scambia, G. (2000). Cancer Chemother. Pharmacol.46, 305–312. [PubMed]
  • Dimmock, J. R., Kandepu, N. M., Hetherington, M., Quail, J. W., Pugazhenthi, U., Sudom, A. M., Chamankhah, M., Rose, P., Pass, E., Allen, T. M., Halleran, S., Szydlowski, J., Mutus, B., Tannous, M., Manavathu, E. K., Myers, T. G., De Clercq, E. & Balzarini, J. (1998). J. Med. Chem.41, 1014–1026. [PubMed]
  • Guo, H.-M., Liu, L. & Jian, F.-F. (2008). Acta Cryst. E64, o1626. [PMC free article] [PubMed]
  • Hsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res.15, 39–46. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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