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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3013.
Published online 2009 November 7. doi:  10.1107/S1600536809045759
PMCID: PMC2971992

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

Abstract

The title compound, C16H13FO2, was prepared from 4-methoxy­hypnone and 2-fluoro­benzophenone by a Claisen–Schmidt condensation reaction. The dihedral angle between the two benzene rings is 31.99 (2)°. In the crystal structure, mol­ecules are linked by weak inter­molecular C—H(...)O hydrogen bonds along [010].

Related literature

For the biological activity of chalcones, see: Hsieh et al. (1998 [triangle]); Anto et al. (1994 [triangle]); De Vincenzo et al. (2000 [triangle]); Dimmock et al. (1998 [triangle]). For related structures, see: Fun et al. (2008 [triangle]); Zhao et al. (2009 [triangle]).

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Object name is e-65-o3013-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-o3013-efi1.jpg
  • a = 7.4511 (6) Å
  • b = 11.0541 (8) Å
  • c = 31.031 (3) Å
  • V = 2555.9 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.30 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 15509 measured reflections
  • 3162 independent reflections
  • 2162 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.117
  • S = 1.05
  • 3162 reflections
  • 173 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.19 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/S1600536809045759/lh2941sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045759/lh2941Isup2.hkl

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

Acknowledgments

The author would like to thank the Natural Science Foundation of Shandong Province (Y2008B29) and the Yuan-Du Scholar Fund of Weifang City.

supplementary crystallographic information

Comment

Chalcones have been identified as interesting compounds having multiple biological activities which include antiinflammatory (Hsieh et al.,1998) and antioxidant (Anto et al.,1994). The effectiveness of chalcone compounds against 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 herein.

The molecular structure of (I) is shown in Fig.1. The dihedral angle between the two benzene rings (C1—C6 and C7—C12) is 31.99 (2)°. The bond lengths and bond angles are within normal ranges and comparable to those in a related structures (Fun et al., 2008; Zhao et al., 2009). In the crystal structure, molecules are linked by weak intermolecular C-H···O hydrogen bonds into one-dimensional chains along [010] (Fig. 2).

Experimental

A mixture of 4-methoxyhypnone (0.02 mol) and 2-fluorobenzophenone (0.02 mol) and 10% NaOH (10ml) was stirred in ethanol (30 ml) for 2 h to afford the title compound (yield 85%). Single crystals suitable for X-ray measurements were obtailed by recrystallization of an ethyl acetate solution of the title compound at room temperature.

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq 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 30% probability level.

Crystal data

C16H13FO2F(000) = 1072
Mr = 256.26Dx = 1.332 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2162 reflections
a = 7.4511 (6) Åθ = 2.6–28.4°
b = 11.0541 (8) ŵ = 0.10 mm1
c = 31.031 (3) ÅT = 298 K
V = 2555.9 (3) Å3Bar, yellow
Z = 80.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer2162 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 28.4°, θmin = 2.6°
[var phi] and ω scansh = −8→9
15509 measured reflectionsk = −13→14
3162 independent reflectionsl = −39→36

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.117w = 1/[σ2(Fo2) + (0.0479P)2 + 0.3713P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3162 reflectionsΔρmax = 0.16 e Å3
173 parametersΔρmin = −0.19 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: 0.0083 (9)

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
C90.14251 (16)0.07378 (11)0.24089 (4)0.0474 (3)
C160.16025 (17)0.04544 (11)0.19449 (5)0.0530 (3)
O20.20708 (16)−0.05586 (9)0.18272 (3)0.0723 (3)
C110.06705 (19)0.20676 (12)0.30007 (4)0.0539 (3)
H11A0.02710.28170.30970.065*
C100.08333 (18)0.18431 (11)0.25647 (4)0.0507 (3)
H10A0.05370.24510.23700.061*
C120.11063 (18)0.11693 (12)0.32916 (4)0.0548 (3)
C150.0866 (2)0.11137 (13)0.12171 (5)0.0598 (4)
H15A0.10290.03070.11420.072*
C140.11574 (19)0.13923 (12)0.16225 (5)0.0565 (4)
H14A0.10820.21970.17090.068*
O10.09938 (16)0.12870 (10)0.37267 (3)0.0747 (3)
C40.03134 (19)0.19281 (13)0.08723 (4)0.0567 (4)
C80.1842 (2)−0.01562 (12)0.27107 (5)0.0597 (4)
H8A0.2232−0.09090.26160.072*
F−0.04947 (18)0.02464 (10)0.04543 (3)0.1056 (4)
C70.1688 (2)0.00549 (13)0.31425 (5)0.0656 (4)
H7A0.1975−0.05530.33380.079*
C50.0374 (2)0.31898 (13)0.09031 (5)0.0638 (4)
H5A0.08620.35460.11480.077*
C3−0.0402 (2)0.14689 (15)0.04940 (5)0.0698 (4)
C6−0.0271 (3)0.39113 (16)0.05794 (5)0.0783 (5)
H6A−0.02270.47480.06080.094*
C130.0495 (2)0.24277 (16)0.39010 (5)0.0743 (5)
H13A0.04650.23760.42100.112*
H13B−0.06710.26490.37960.112*
H13C0.13540.30280.38150.112*
C2−0.1052 (3)0.21693 (19)0.01653 (5)0.0822 (5)
H2A−0.15250.1818−0.00820.099*
C1−0.0987 (3)0.3404 (2)0.02105 (5)0.0849 (5)
H1A−0.14260.3900−0.00080.102*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C90.0380 (6)0.0385 (6)0.0657 (8)−0.0049 (5)−0.0016 (5)0.0041 (5)
C160.0447 (7)0.0411 (7)0.0731 (9)−0.0071 (5)0.0028 (6)−0.0035 (6)
O20.0834 (8)0.0458 (6)0.0876 (8)0.0051 (5)0.0089 (6)−0.0080 (5)
C110.0565 (8)0.0436 (7)0.0616 (8)−0.0001 (6)−0.0029 (6)0.0026 (6)
C100.0531 (8)0.0393 (6)0.0597 (8)−0.0011 (6)−0.0050 (6)0.0066 (5)
C120.0481 (7)0.0579 (8)0.0585 (8)−0.0039 (6)−0.0017 (6)0.0110 (6)
C150.0627 (9)0.0495 (7)0.0672 (9)−0.0063 (7)0.0071 (7)−0.0087 (6)
C140.0617 (9)0.0461 (7)0.0616 (8)−0.0032 (6)0.0036 (6)−0.0055 (6)
O10.0864 (8)0.0769 (7)0.0608 (7)0.0062 (6)−0.0007 (5)0.0141 (5)
C40.0545 (8)0.0621 (8)0.0535 (8)−0.0062 (7)0.0087 (6)−0.0085 (6)
C80.0562 (8)0.0419 (7)0.0809 (10)0.0065 (6)0.0026 (7)0.0073 (6)
F0.1581 (12)0.0820 (7)0.0768 (7)−0.0307 (7)−0.0027 (6)−0.0256 (5)
C70.0654 (9)0.0541 (8)0.0773 (10)0.0088 (7)−0.0005 (8)0.0223 (7)
C50.0702 (10)0.0624 (9)0.0587 (8)−0.0028 (8)0.0039 (7)−0.0065 (7)
C30.0782 (11)0.0721 (10)0.0592 (9)−0.0144 (8)0.0106 (8)−0.0159 (8)
C60.0958 (13)0.0692 (10)0.0698 (10)0.0077 (9)0.0080 (9)0.0008 (8)
C130.0755 (11)0.0871 (12)0.0604 (9)−0.0049 (9)−0.0012 (8)0.0005 (8)
C20.0839 (12)0.1103 (15)0.0525 (9)−0.0108 (11)0.0016 (8)−0.0104 (9)
C10.0877 (13)0.1064 (15)0.0607 (10)0.0128 (11)0.0051 (9)0.0075 (10)

Geometric parameters (Å, °)

C9—C101.3859 (18)C4—C51.399 (2)
C9—C81.3964 (18)C8—C71.365 (2)
C9—C161.4794 (19)C8—H8A0.9300
C16—O21.2285 (15)F—C31.3587 (19)
C16—C141.478 (2)C7—H7A0.9300
C11—C121.3807 (18)C5—C61.370 (2)
C11—C101.3808 (19)C5—H5A0.9300
C11—H11A0.9300C3—C21.369 (2)
C10—H10A0.9300C6—C11.382 (2)
C12—O11.3591 (17)C6—H6A0.9300
C12—C71.385 (2)C13—H13A0.9600
C15—C141.3134 (19)C13—H13B0.9600
C15—C41.457 (2)C13—H13C0.9600
C15—H15A0.9300C2—C11.373 (3)
C14—H14A0.9300C2—H2A0.9300
O1—C131.421 (2)C1—H1A0.9300
C4—C31.386 (2)
C10—C9—C8117.44 (13)C7—C8—H8A119.4
C10—C9—C16123.68 (12)C9—C8—H8A119.4
C8—C9—C16118.87 (12)C8—C7—C12120.40 (13)
O2—C16—C14120.11 (13)C8—C7—H7A119.8
O2—C16—C9120.52 (13)C12—C7—H7A119.8
C14—C16—C9119.34 (11)C6—C5—C4121.29 (15)
C12—C11—C10119.38 (13)C6—C5—H5A119.4
C12—C11—H11A120.3C4—C5—H5A119.4
C10—C11—H11A120.3F—C3—C2118.48 (15)
C11—C10—C9121.88 (12)F—C3—C4117.44 (15)
C11—C10—H10A119.1C2—C3—C4124.06 (16)
C9—C10—H10A119.1C5—C6—C1120.44 (17)
O1—C12—C11124.49 (13)C5—C6—H6A119.8
O1—C12—C7115.86 (12)C1—C6—H6A119.8
C11—C12—C7119.65 (13)O1—C13—H13A109.5
C14—C15—C4127.23 (13)O1—C13—H13B109.5
C14—C15—H15A116.4H13A—C13—H13B109.5
C4—C15—H15A116.4O1—C13—H13C109.5
C15—C14—C16121.39 (13)H13A—C13—H13C109.5
C15—C14—H14A119.3H13B—C13—H13C109.5
C16—C14—H14A119.3C3—C2—C1118.28 (16)
C12—O1—C13118.62 (12)C3—C2—H2A120.9
C3—C4—C5115.82 (14)C1—C2—H2A120.9
C3—C4—C15120.28 (14)C2—C1—C6120.11 (17)
C5—C4—C15123.83 (13)C2—C1—H1A119.9
C7—C8—C9121.24 (13)C6—C1—H1A119.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11A···O2i0.932.513.3679 (18)153

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: LH2941).

References

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  • Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.
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