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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2805.
Published online 2009 October 23. doi:  10.1107/S1600536809041877
PMCID: PMC2971044

1-Phenyl-3-(2,4,6-trimethoxy­phen­yl)prop-2-en-1-one

Abstract

In the title compound, C18H18O4, a derivative of biologically active chalcones, the dihedral angle between the two rings is 7.43 (7)°. The molecule adopts an E configuration about the central olefinic bonds. In the crystal, there are no strong inter­actions between the mol­ecules.

Related literature

For related structures, see: Subbiah Pandi et al. (2003 [triangle]); Low et al. (2002 [triangle]); Yathirajan et al. (2006 [triangle]); Suwunwong et al. (2009 [triangle]); Jasinski et al. (2009 [triangle]). For background to and applications of chalcones, see: Dimmock et al. (1999 [triangle]); Sivakumar et al. (2009 [triangle]); Echeverria et al. (2009 [triangle]); Kontogiorgis et al. (2008 [triangle]); Dominguez et al. (2005 [triangle]); Nowakowska (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2805-scheme1.jpg

Experimental

Crystal data

  • C18H18O4
  • M r = 298.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2805-efi1.jpg
  • a = 9.0052 (10) Å
  • b = 14.9245 (17) Å
  • c = 11.7658 (14) Å
  • β = 104.315 (2)°
  • V = 1532.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 273 K
  • 0.12 × 0.10 × 0.05 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.989, T max = 0.996
  • 7895 measured reflections
  • 2701 independent reflections
  • 2125 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.132
  • S = 1.00
  • 2701 reflections
  • 203 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041877/wn2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041877/wn2350Isup2.hkl

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

Acknowledgments

This work was supported by Zhejiang Province Extremely Key Subject Building Funding (Pharmacology and Biochemical Pharmaceutics 2008), the Department of Education of Zhejiang Province (No. 20070907) and the Wenzhou Administration of Science and Technology project (No. Y20080016).

supplementary crystallographic information

Comment

Chalcones, which have the common skeleton of 1,3-diaryl-2-propen-1-ones, are natural products, distributed widely in fruits, vegetables etc. Natural and synthetical chalcones have wide-ranging biological properties, including antimicrobial, antifungal, antioxidant, antiangiogenic, antitumor and anti-inflammatory activities (Dimmock et al., 1999; Sivakumar et al., 2009; Echeverria et al., 2009; Kontogiorgis et al., 2008). The chalcone derivatives with trimethoxyphenyl substitution have also been reported to have a wide range of biological activities (Suwunwong et al., 2009; Jasinski et al., 2009; Dominguez et al., 2005; Nowakowska, 2007).

The present investigation is a continuation of our broad program of work on the synthesis and structural study of chalcones and their derivatives. Investigation of these structures may be helpful in the design and synthesis of new compounds. In order to understand the geometrical features and the underlying intermolecular interactions which hold the assembly of molecules in the crystal structure, an X-ray study of the title compound was carried out.

It is approximately planar and the dihedral angle between the two rings is 7.43 (7)°. The H atoms of the central propenone group are trans. The average value of the bond distances [1.385 (5) Å] and exocyclic bond angles [120.7 (4)°] in the benzene and phenyl rings have normal values which agree quite well with the values reported in the literature for some analogous structures (Subbiah Pandi et al., 2003; Low et al., 2002; Yathirajan et al., 2006).

Experimental

Acetophenone (15 mmol) was dissolved in ethanol (5 ml) and crushed KOH (15 mmol) was added. The flask was immersed in a bath of crushed ice and a solution of 2,4,6-trimethoxybenzaldehyde (15 mmol) in ethanol (5 mmol) was added. The reaction mixture was stirred at 300 K and completion of the reaction was monitored by thin-layer chromatography. Ice-cold water was added to the reaction mixture after 48 h and the yellow solid that separated was filtered off, washed with water and cold ethanol, dried and purified by column chromatography on silica gel (yield:68%). Single crystals of the title compound were grown in a CH2Cl2/CH3OH mixture (5:2 v/v) by slow evaporation (mp 436–437 K).

Refinement

The H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% displacement ellipsoids for the non-hydrogen atoms. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H18O4F(000) = 632
Mr = 298.32Dx = 1.293 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3499 reflections
a = 9.0052 (10) Åθ = 2.7–27.9°
b = 14.9245 (17) ŵ = 0.09 mm1
c = 11.7658 (14) ÅT = 273 K
β = 104.315 (2)°Block, colorless
V = 1532.2 (3) Å30.12 × 0.10 × 0.05 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer2701 independent reflections
Radiation source: fine-focus sealed tube2125 reflections with I > 2σ(I)
graphiteRint = 0.044
[var phi] and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −10→10
Tmin = 0.989, Tmax = 0.996k = −17→15
7895 measured reflectionsl = −13→13

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) = 0.132w = 1/[σ2(Fo2) + (0.0938P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
2701 reflectionsΔρmax = 0.14 e Å3
203 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.353 (18)

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
C10.9745 (2)−0.05689 (12)0.14050 (16)0.0745 (5)
H1A1.0183−0.03760.21960.112*
H1B1.0548−0.06620.10120.112*
H1C0.9196−0.11190.14150.112*
C20.65289 (18)−0.07567 (10)0.42207 (13)0.0599 (4)
H2A0.6579−0.12850.37650.090*
H2B0.6153−0.09130.48900.090*
H2C0.7534−0.05000.44790.090*
C30.44257 (19)0.21153 (10)−0.08152 (13)0.0619 (4)
H3A0.53730.2441−0.06050.093*
H3B0.36080.2517−0.11660.093*
H3C0.44990.1652−0.13640.093*
C40.74716 (15)0.02951 (9)0.11985 (12)0.0466 (4)
C50.72022 (14)−0.00525 (9)0.22193 (11)0.0462 (4)
H50.7898−0.04430.26870.055*
C60.58735 (14)0.01944 (9)0.25291 (11)0.0424 (4)
C70.47895 (14)0.07868 (8)0.18520 (11)0.0407 (4)
C80.51526 (15)0.11331 (9)0.08332 (11)0.0437 (4)
C90.64562 (16)0.08890 (9)0.05100 (12)0.0483 (4)
H90.66580.1122−0.01700.058*
C100.34214 (15)0.10052 (9)0.22290 (12)0.0456 (4)
H100.33690.07430.29350.055*
C110.22244 (15)0.15177 (10)0.17373 (12)0.0509 (4)
H110.21750.17750.10090.061*
C120.09861 (15)0.16858 (10)0.23113 (12)0.0512 (4)
C13−0.02269 (14)0.23528 (9)0.17775 (12)0.0469 (4)
C14−0.01819 (17)0.28712 (10)0.08031 (13)0.0557 (4)
H140.06000.27840.04260.067*
C15−0.12880 (19)0.35148 (11)0.03909 (15)0.0658 (5)
H15−0.12390.3863−0.02550.079*
C16−0.24600 (18)0.36410 (12)0.09338 (15)0.0665 (5)
H16−0.31970.40790.06610.080*
C17−0.25405 (17)0.31221 (12)0.18758 (15)0.0650 (5)
H17−0.33460.32000.22320.078*
C18−0.14374 (16)0.24862 (11)0.22991 (13)0.0568 (4)
H18−0.15010.21410.29430.068*
O10.09525 (13)0.13297 (9)0.32420 (10)0.0788 (4)
O20.41260 (11)0.17261 (7)0.02032 (8)0.0580 (3)
O30.87208 (11)0.01000 (7)0.08015 (9)0.0645 (4)
O40.55259 (11)−0.01253 (7)0.35229 (9)0.0568 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0661 (10)0.0857 (12)0.0833 (11)0.0327 (9)0.0404 (9)0.0290 (10)
C20.0601 (9)0.0681 (10)0.0523 (9)0.0107 (8)0.0156 (7)0.0195 (7)
C30.0716 (10)0.0603 (10)0.0518 (9)0.0047 (8)0.0115 (8)0.0158 (7)
C40.0438 (7)0.0485 (8)0.0512 (8)0.0025 (6)0.0186 (6)0.0020 (6)
C50.0450 (8)0.0464 (8)0.0483 (8)0.0063 (6)0.0137 (6)0.0071 (6)
C60.0441 (7)0.0449 (7)0.0390 (7)−0.0012 (6)0.0119 (6)0.0025 (6)
C70.0407 (7)0.0426 (7)0.0384 (7)0.0006 (5)0.0088 (5)−0.0029 (5)
C80.0455 (8)0.0414 (7)0.0421 (7)0.0021 (6)0.0067 (6)0.0006 (6)
C90.0540 (8)0.0510 (8)0.0423 (8)0.0014 (6)0.0164 (6)0.0065 (6)
C100.0455 (8)0.0499 (8)0.0409 (7)0.0007 (6)0.0097 (6)−0.0048 (6)
C110.0463 (8)0.0626 (9)0.0430 (8)0.0072 (6)0.0097 (6)−0.0019 (6)
C120.0445 (8)0.0646 (9)0.0433 (8)0.0024 (7)0.0086 (6)−0.0059 (7)
C130.0392 (7)0.0536 (8)0.0460 (8)−0.0003 (6)0.0071 (6)−0.0107 (6)
C140.0504 (8)0.0632 (9)0.0559 (9)0.0055 (7)0.0174 (7)−0.0042 (7)
C150.0666 (10)0.0660 (10)0.0647 (10)0.0118 (8)0.0159 (8)0.0051 (8)
C160.0532 (9)0.0684 (11)0.0751 (11)0.0148 (8)0.0107 (8)−0.0029 (9)
C170.0444 (8)0.0741 (11)0.0801 (12)0.0072 (7)0.0221 (8)−0.0086 (9)
C180.0496 (8)0.0657 (9)0.0580 (9)−0.0010 (7)0.0188 (7)−0.0053 (7)
O10.0688 (8)0.1132 (10)0.0602 (7)0.0294 (7)0.0272 (6)0.0240 (7)
O20.0577 (6)0.0647 (7)0.0522 (6)0.0165 (5)0.0150 (5)0.0177 (5)
O30.0587 (7)0.0769 (8)0.0675 (7)0.0206 (5)0.0340 (6)0.0224 (5)
O40.0533 (6)0.0719 (7)0.0500 (6)0.0154 (5)0.0216 (5)0.0200 (5)

Geometric parameters (Å, °)

C1—O31.4241 (17)C8—O21.3596 (15)
C1—H1A0.9600C8—C91.3697 (19)
C1—H1B0.9600C9—H90.9300
C1—H1C0.9600C10—C111.3317 (19)
C2—O41.4182 (16)C10—H100.9300
C2—H2A0.9600C11—C121.4611 (19)
C2—H2B0.9600C11—H110.9300
C2—H2C0.9600C12—O11.2244 (17)
C3—O21.4163 (17)C12—C131.496 (2)
C3—H3A0.9600C13—C181.391 (2)
C3—H3B0.9600C13—C141.392 (2)
C3—H3C0.9600C14—C151.382 (2)
C4—O31.3521 (16)C14—H140.9300
C4—C91.3827 (19)C15—C161.375 (2)
C4—C51.3836 (19)C15—H150.9300
C5—C61.3842 (17)C16—C171.369 (2)
C5—H50.9300C16—H160.9300
C6—O41.3688 (15)C17—C181.375 (2)
C6—C71.4088 (18)C17—H170.9300
C7—C81.4158 (18)C18—H180.9300
C7—C101.4461 (18)
O3—C1—H1A109.5C8—C9—C4119.73 (12)
O3—C1—H1B109.5C8—C9—H9120.1
H1A—C1—H1B109.5C4—C9—H9120.1
O3—C1—H1C109.5C11—C10—C7130.97 (13)
H1A—C1—H1C109.5C11—C10—H10114.5
H1B—C1—H1C109.5C7—C10—H10114.5
O4—C2—H2A109.5C10—C11—C12121.74 (13)
O4—C2—H2B109.5C10—C11—H11119.1
H2A—C2—H2B109.5C12—C11—H11119.1
O4—C2—H2C109.5O1—C12—C11121.96 (13)
H2A—C2—H2C109.5O1—C12—C13119.16 (13)
H2B—C2—H2C109.5C11—C12—C13118.79 (13)
O2—C3—H3A109.5C18—C13—C14117.99 (13)
O2—C3—H3B109.5C18—C13—C12118.71 (13)
H3A—C3—H3B109.5C14—C13—C12123.26 (12)
O2—C3—H3C109.5C15—C14—C13120.66 (14)
H3A—C3—H3C109.5C15—C14—H14119.7
H3B—C3—H3C109.5C13—C14—H14119.7
O3—C4—C9114.95 (12)C14—C15—C16120.09 (16)
O3—C4—C5123.95 (12)C14—C15—H15120.0
C9—C4—C5121.09 (12)C16—C15—H15120.0
C6—C5—C4118.50 (12)C15—C16—C17119.95 (15)
C6—C5—H5120.7C15—C16—H16120.0
C4—C5—H5120.7C17—C16—H16120.0
O4—C6—C5121.82 (11)C16—C17—C18120.38 (14)
O4—C6—C7115.41 (11)C16—C17—H17119.8
C5—C6—C7122.77 (11)C18—C17—H17119.8
C6—C7—C8115.79 (11)C13—C18—C17120.91 (15)
C6—C7—C10119.45 (11)C13—C18—H18119.6
C8—C7—C10124.75 (12)C17—C18—H18119.5
O2—C8—C9122.39 (12)C8—O2—C3118.82 (11)
O2—C8—C7115.53 (11)C4—O3—C1118.07 (11)
C9—C8—C7122.08 (12)C6—O4—C2118.61 (10)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2350).

References

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