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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2515.
Published online 2009 September 26. doi:  10.1107/S1600536809037635
PMCID: PMC2970387

(E)-3-(4-Fluoro­phen­yl)-1-phenyl-2-propen-1-one

Abstract

In the title compound, C15H11FO, the configuration of the keto group with respect to the olefinic double bond is s–cis. The dihedral angle between the planes of the two benzene rings is 10.61 (10)°. The crystal packing is stabilized by C—H(...)π inter­actions involving both benzene rings.

Related literature

For the synthesis, see: Chimenti et al. (2008 [triangle]). For the biological activity of chalcone derivatives, see: Dimmock et al. (1999 [triangle]).

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Object name is e-65-o2515-scheme1.jpg

Experimental

Crystal data

  • C15H11FO
  • M r = 226.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2515-efi1.jpg
  • a = 24.926 (9) Å
  • b = 5.6940 (19) Å
  • c = 7.749 (3) Å
  • β = 94.747 (5)°
  • V = 1096.0 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 93 K
  • 0.40 × 0.33 × 0.30 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: none
  • 4214 measured reflections
  • 1256 independent reflections
  • 1174 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.066
  • S = 1.05
  • 1256 reflections
  • 154 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037635/ci2914sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037635/ci2914Isup2.hkl

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

Acknowledgments

The author thanks the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

supplementary crystallographic information

Comment

Chalcone derivatives are a class of important compounds that possess antiprotzoal, antihelmintic, amoebicidal, anti-ulcer, antiviral, insecticidal, antibacterial, anticancer, cytotoxic and immunosuppressive activities (Dimmock et al., 1999). The author reports here the crystal structure of the title compound, a chalocone derivative.

Bond lengths and angles in the title molecule (Fig.1) are normal. The configuration of the keto group with respect to the olefinic double bond is s-cis, with a O1—C7—C8—C9 torsion angle of -7.1 (3)°. The C1-C6 and C10-C15 benzene rings form a dihedral angle of 10.61 (10)°.

The crystal packing is stabilized by C—H···π interactions involving both benzene rings (Table 1; Cg1 and Cg2 are centroids of the C1-C6 and C10-C15 rings, respectively).

Experimental

The title compound was synthesized according to the method reported in the literature (Chimenti et al., 2008). Colourless single crystals suitable for X-ray diffraction were obtained by slow evaporation of a acetone solution of the compound.

Refinement

H atoms were placed in calculated positions, with C-H = 0.95 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.

Crystal data

C15H11FOF(000) = 472
Mr = 226.24Dx = 1.371 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1803 reflections
a = 24.926 (9) Åθ = 3.2–27.5°
b = 5.6940 (19) ŵ = 0.10 mm1
c = 7.749 (3) ÅT = 93 K
β = 94.747 (5)°Block, colourless
V = 1096.0 (6) Å30.40 × 0.33 × 0.30 mm
Z = 4

Data collection

Rigaku SPIDER diffractometer1174 reflections with I > 2σ(I)
Radiation source: Rotating anodeRint = 0.027
graphiteθmax = 27.5°, θmin = 3.3°
ω scansh = −32→32
4214 measured reflectionsk = −7→6
1256 independent reflectionsl = −10→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.02P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3
1256 reflections(Δ/σ)max = 0.010
154 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = −0.14 e Å3

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
F10.78252 (5)−0.0769 (2)0.41272 (15)0.0283 (3)
O10.54146 (6)0.8936 (3)0.5750 (2)0.0298 (4)
C10.43870 (9)0.9349 (4)0.4181 (3)0.0201 (5)
H10.45261.05840.49120.024*
C20.38614 (9)0.9458 (4)0.3436 (3)0.0224 (5)
H20.36421.07670.36600.027*
C30.36564 (8)0.7667 (4)0.2369 (3)0.0220 (5)
H30.32960.77490.18680.026*
C40.39742 (9)0.5758 (4)0.2026 (3)0.0222 (5)
H40.38340.45390.12820.027*
C50.45022 (9)0.5632 (4)0.2780 (3)0.0205 (5)
H50.47200.43150.25550.025*
C60.47111 (8)0.7420 (4)0.3855 (3)0.0180 (4)
C70.52705 (8)0.7380 (4)0.4726 (3)0.0205 (4)
C80.56390 (9)0.5435 (4)0.4363 (3)0.0217 (5)
H80.55120.41420.36690.026*
C90.61504 (8)0.5513 (4)0.5016 (3)0.0199 (4)
H90.62500.68360.57180.024*
C100.65773 (9)0.3806 (4)0.4783 (3)0.0185 (4)
C110.64836 (9)0.1657 (4)0.3938 (3)0.0214 (5)
H110.61270.12390.35260.026*
C120.69023 (9)0.0130 (4)0.3692 (3)0.0225 (5)
H120.6838−0.13100.30910.027*
C130.74170 (9)0.0754 (4)0.4343 (3)0.0211 (5)
C140.75290 (8)0.2834 (4)0.5203 (3)0.0212 (4)
H140.78860.32160.56350.025*
C150.71063 (9)0.4355 (4)0.5420 (3)0.0207 (4)
H150.71760.57990.60120.025*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0222 (7)0.0284 (7)0.0342 (8)0.0079 (6)0.0022 (5)0.0009 (6)
O10.0228 (8)0.0330 (9)0.0326 (9)0.0047 (7)−0.0034 (7)−0.0121 (8)
C10.0228 (11)0.0192 (11)0.0185 (11)−0.0002 (9)0.0021 (8)−0.0011 (9)
C20.0221 (11)0.0227 (11)0.0227 (11)0.0043 (9)0.0032 (9)0.0017 (9)
C30.0177 (10)0.0265 (11)0.0218 (11)0.0006 (9)0.0017 (9)0.0031 (9)
C40.0218 (11)0.0232 (11)0.0215 (11)−0.0036 (9)0.0012 (8)−0.0011 (9)
C50.0218 (11)0.0205 (11)0.0196 (10)0.0027 (9)0.0046 (9)0.0002 (9)
C60.0177 (10)0.0206 (11)0.0161 (10)0.0007 (8)0.0031 (8)0.0028 (8)
C70.0187 (10)0.0230 (11)0.0199 (10)0.0001 (9)0.0026 (8)0.0005 (9)
C80.0228 (10)0.0215 (11)0.0206 (10)0.0014 (9)0.0012 (8)−0.0019 (9)
C90.0209 (10)0.0209 (11)0.0178 (10)0.0023 (9)0.0012 (8)−0.0003 (9)
C100.0179 (10)0.0210 (10)0.0163 (10)0.0021 (9)0.0004 (8)0.0033 (9)
C110.0177 (10)0.0249 (11)0.0211 (11)−0.0018 (9)−0.0013 (8)0.0021 (9)
C120.0247 (11)0.0222 (11)0.0206 (11)0.0014 (9)0.0012 (9)0.0005 (9)
C130.0191 (11)0.0229 (11)0.0217 (12)0.0047 (9)0.0040 (8)0.0042 (9)
C140.0155 (10)0.0259 (11)0.0218 (10)−0.0017 (9)−0.0005 (8)0.0030 (10)
C150.0214 (11)0.0204 (10)0.0199 (11)−0.0005 (9)−0.0009 (8)0.0004 (9)

Geometric parameters (Å, °)

F1—C131.358 (2)C8—C91.333 (3)
O1—C71.223 (3)C8—H80.95
C1—C21.389 (3)C9—C101.463 (3)
C1—C61.399 (3)C9—H90.95
C1—H10.95C10—C111.398 (3)
C2—C31.384 (3)C10—C151.404 (3)
C2—H20.95C11—C121.383 (3)
C3—C41.384 (3)C11—H110.95
C3—H30.95C12—C131.386 (3)
C4—C51.397 (3)C12—H120.95
C4—H40.95C13—C141.376 (3)
C5—C61.389 (3)C14—C151.385 (3)
C5—H50.95C14—H140.95
C6—C71.498 (3)C15—H150.95
C7—C81.481 (3)
C2—C1—C6119.9 (2)C7—C8—H8120.3
C2—C1—H1120.0C8—C9—C10127.8 (2)
C6—C1—H1120.0C8—C9—H9116.1
C3—C2—C1120.3 (2)C10—C9—H9116.1
C3—C2—H2119.8C11—C10—C15118.37 (19)
C1—C2—H2119.8C11—C10—C9122.95 (19)
C2—C3—C4120.3 (2)C15—C10—C9118.68 (19)
C2—C3—H3119.8C12—C11—C10121.0 (2)
C4—C3—H3119.8C12—C11—H11119.5
C3—C4—C5119.6 (2)C10—C11—H11119.5
C3—C4—H4120.2C11—C12—C13118.4 (2)
C5—C4—H4120.2C11—C12—H12120.8
C6—C5—C4120.43 (19)C13—C12—H12120.8
C6—C5—H5119.8F1—C13—C14119.03 (19)
C4—C5—H5119.8F1—C13—C12118.19 (19)
C5—C6—C1119.37 (19)C14—C13—C12122.8 (2)
C5—C6—C7123.20 (18)C13—C14—C15118.11 (19)
C1—C6—C7117.42 (18)C13—C14—H14120.9
O1—C7—C8120.79 (19)C15—C14—H14120.9
O1—C7—C6119.56 (19)C14—C15—C10121.3 (2)
C8—C7—C6119.64 (18)C14—C15—H15119.3
C9—C8—C7119.4 (2)C10—C15—H15119.3
C9—C8—H8120.3
C6—C1—C2—C3−0.1 (3)C7—C8—C9—C10−178.7 (2)
C1—C2—C3—C4−0.3 (3)C8—C9—C10—C11−6.7 (3)
C2—C3—C4—C50.7 (3)C8—C9—C10—C15172.6 (2)
C3—C4—C5—C6−0.6 (3)C15—C10—C11—C12−1.7 (3)
C4—C5—C6—C10.2 (3)C9—C10—C11—C12177.7 (2)
C4—C5—C6—C7179.0 (2)C10—C11—C12—C131.6 (3)
C2—C1—C6—C50.2 (3)C11—C12—C13—F1178.78 (19)
C2—C1—C6—C7−178.7 (2)C11—C12—C13—C14−0.8 (3)
C5—C6—C7—O1−175.0 (2)F1—C13—C14—C15−179.54 (18)
C1—C6—C7—O13.9 (3)C12—C13—C14—C150.0 (3)
C5—C6—C7—C84.0 (3)C13—C14—C15—C10−0.1 (3)
C1—C6—C7—C8−177.2 (2)C11—C10—C15—C140.9 (3)
O1—C7—C8—C9−7.1 (3)C9—C10—C15—C14−178.5 (2)
C6—C7—C8—C9174.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···Cg1i0.952.893.592 (3)132
C4—H4···Cg1ii0.952.933.646 (6)133
C12—H12···Cg2iii0.952.853.505 (8)127

Symmetry codes: (i) x+1/2, y+5/2, z; (ii) x+1/2, y+3/2, z−1; (iii) x+1/2, y+1/2, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2914).

References

  • Chimenti, F., Fioravanti, R., Bolasco, A., Manna, F., Chimenti, P., Secci, D., Rossi, F., Turini, P., Ortuso, F., Alcaro, S. & Cardia, M. C. (2008). Eur. J. Med. Chem.43, 2262–2267. [PubMed]
  • Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem.6, 1125–1149. [PubMed]
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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