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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2346–o2347.
Published online 2010 August 18. doi:  10.1107/S1600536810032514
PMCID: PMC3007889

(E)-3-(4-Eth­oxy­phen­yl)-1-(2-hy­droxy­phen­yl)prop-2-en-1-one

Abstract

In the title compound, C17H16O3, the carbonyl group is in an s-cis configuration with respect to the olefinic double bond. The dihedral angle between the two benzene rings is 2.85 (3)°. The prop-2-en-1-one bridge makes dihedral angles of 4.77 (4) and 4.15 (4)°, respectively, with the 2-hy­droxy­phenyl and 4-eth­oxy­phenyl rings. The eth­oxy group is coplanar with the attached phenyl ring [Car—O—C—C = 179.72 (5)°]. An intra­molecular O—H(...)O hydrogen bond generates an S(6) ring motif. In the crystal structure, mol­ecules are stacked in an anti­parallel manner to form columns along the b axis. The columnar structure is stabilized by C—H(...)π inter­actions involving the 2-hy­droxy­phenyl ring.

Related literature

For background on the applications of chalcones, see: Jun et al. (2007 [triangle]); Nowakowska (2007 [triangle]); Patil & Dharmaprakash (2008 [triangle]); Saydam et al. (2003 [triangle]); Svetlichny et al. (2007 [triangle]); Tewtrakul et al. (2003 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For related structures, see: Fun et al. (2008 [triangle]); Patil et al. (2007 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2346-scheme1.jpg

Experimental

Crystal data

  • C17H16O3
  • M r = 268.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2346-efi1.jpg
  • a = 6.8305 (2) Å
  • b = 6.8790 (2) Å
  • c = 14.8188 (3) Å
  • α = 88.533 (1)°
  • β = 80.380 (1)°
  • γ = 77.469 (1)°
  • V = 670.11 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.60 × 0.38 × 0.36 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.948, T max = 0.969
  • 24772 measured reflections
  • 5849 independent reflections
  • 5179 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.124
  • S = 1.04
  • 5848 reflections
  • 186 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032514/ci5143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032514/ci5143Isup2.hkl

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

Acknowledgments

The authors thank the Thailand Research Fund (TRF) for the research grant (grant No. RSA 5280033) and the Prince of Songkla University for financial support. The authors also thank the Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University is acknowledged for the bacterial assay.

supplementary crystallographic information

Comment

Chalcones is an interesting class of compounds which have been reported to posses various useful properties such as non-linear optical (NLO) (Patil & Dharmaprakash, 2008) and fluorescent properties (Svetlichny et al., 2007). Synthetic and naturally occurring chalcones have been found to exhibit many useful biological activities, including anti-inflammatory, antileishmanial, antimicrobial, antioxidant (Nowakowska, 2007; Saydam et al., 2003), HIV-1 protease inhibitory (Tewtrakul et al., 2003) and tyrosinase inhibitory (Jun et al., 2007) activities. Our on going research on NLO properties and bioactivities of the synthetic chalcones led us to synthesize the title chalcone in order to study its NLO properties, antibacterial and tyrosinase inhibitory activities. The results show that the title compound, (I), crystallized in centrosymmetric P1 space group which prohibits the second order NLO properties. Our biological testing found that (I) was inactive against the tested bacteria which are Gram-positive bacteria i.e. Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Methicillin-Resistant Staphylococcus aureus and Vancomycin-Resistant Enterococcus faecalis and Gram-negative bacteria i.e. Pseudomonas aeruginosa, Salmonella typhi and Shigella sonnei. Nevertheless (I) shows moderate tyrosinase inhibitory activity which will be reported elsewhere with some other chalcones. Herein the crystal structure of (I) is reported.

The title molecule (Fig. 1) exists in an E configuration with respect to the C8═C9 ethenyl bond [1.3475 (8) Å]; the C7–C8–C9–C10 torsion angle is -178.73 (6)°. The molecule is almost planar with the dihedral angle between the 2-hydroxyphenyl and 4-ethoxyphenyl rings being 2.85 (3)°. The substituted ethoxy group is coplanar with the attached phenyl ring with the torsion angle C13–O3–C16–C17 = 179.72 (5)°. The prop-2-en-1-one unit (C7–C9/O1) is planar [r.m.s. deviation 0.0098 (1) Å] and the torsion angle O1–C7–C8–C9 being 3.15 (10)°. This bridge makes dihedral angles of 4.77 (4) and 4.15 (4)° with the 2-hydroxyphenyl and 4-ethoxyphenyl rings, respectively. Intramolecular O2—H1O2···O1 hydrogen bond generates an S(6) ring motif (Fig. 1) (Bernstein et al., 1995) which helps to stabilize the planarity of the chalcone skeleton. The bond distances are of normal values (Allen et al., 1987) and are comparable with those observed in related structures (Fun et al., 2008; Patil et al., 2007).

In the crystal packing, the molecules are stacked in an antiparallel manner into columns along the b axis (Fig. 2). This arrangement is stabilized by C—H···π interactions (Table 1) involving the hydroxy phenyl ring. In addition C···O short contacts [3.2894 (8)–3.4003 (9) Å] were also observed.

Experimental

The title compound was synthesized by the condensation of 4-ethoxycarboxaldehyde (0.30 g, 2 mmol) with 2-hydroxyacetophenone (0.24 ml, 2 mmol) in ethanol (40 ml) in the presence of 30% aqueous NaOH (5 ml) at room temperature. After stirring for 3 h, 20% H2SO4(aq) (5 ml) was added dropwise into the solution. After the reaction mixture was kept at room temperature for a day, a yellow solid appeared and was then collected by filtration, washed with acetone and dried in air. Yellow block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from acetone by slow evaporation of the solvent at room temperature after several days (m.p. 387–388 K).

Refinement

Hydroxyl H atom was located in a difference map and refined isotropically. The remaining H atoms were placed in calculated positions, with C–H = 0.93 Å, Uiso = 1.2Ueq(C) for aromatic and CH, C–H = 0.96 Å, Uiso = 1.2Ueq(C) for CH2, and C–H = 0.97 Å, Uiso = 1.5Ueq(C) for CH3 atoms. A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular O—H···O hydrogen bond is shown as a dashed line.
Fig. 2.
The crystal packing of the title compound viewed along the a axis, showing antiparallel stacked columns running along the b axis.

Crystal data

C17H16O3Z = 2
Mr = 268.30F(000) = 284
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Melting point = 387–388 K
a = 6.8305 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.8790 (2) ÅCell parameters from 5849 reflections
c = 14.8188 (3) Åθ = 1.4–35.0°
α = 88.533 (1)°µ = 0.09 mm1
β = 80.380 (1)°T = 100 K
γ = 77.469 (1)°Block, yellow
V = 670.11 (3) Å30.60 × 0.38 × 0.36 mm

Data collection

Bruker APEXII CCD area-detector diffractometer5849 independent reflections
Radiation source: sealed tube5179 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 35.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −11→11
Tmin = 0.948, Tmax = 0.969k = −10→11
24772 measured reflectionsl = −23→23

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0744P)2 + 0.1118P] where P = (Fo2 + 2Fc2)/3
5848 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = −0.44 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O11.46060 (7)0.63044 (8)0.13054 (3)0.01858 (10)
O21.59166 (7)0.61854 (8)0.27959 (4)0.01890 (11)
H1O21.589 (2)0.614 (2)0.2173 (11)0.052 (4)*
O30.61756 (7)0.84310 (8)−0.23045 (3)0.01749 (10)
C11.39580 (9)0.65747 (9)0.32040 (4)0.01353 (11)
C21.35615 (10)0.66707 (10)0.41620 (4)0.01724 (12)
H2A1.46360.64740.44900.021*
C31.15843 (11)0.70553 (11)0.46221 (5)0.02141 (13)
H3A1.13330.71230.52580.026*
C40.99566 (11)0.73437 (12)0.41364 (5)0.02221 (14)
H4A0.86260.75940.44480.027*
C51.03359 (10)0.72550 (10)0.31877 (4)0.01683 (12)
H5A0.92480.74470.28690.020*
C61.23305 (9)0.68816 (9)0.26988 (4)0.01237 (10)
C71.27920 (9)0.67709 (9)0.16865 (4)0.01267 (10)
C81.11547 (9)0.72198 (9)0.11403 (4)0.01350 (11)
H8A0.98110.76300.14250.016*
C91.16056 (9)0.70358 (9)0.02217 (4)0.01346 (11)
H9A1.29720.6595−0.00240.016*
C101.01927 (9)0.74506 (9)−0.04275 (4)0.01229 (10)
C110.80665 (9)0.79158 (9)−0.01582 (4)0.01357 (11)
H11A0.75170.79990.04610.016*
C120.67867 (9)0.82501 (9)−0.08002 (4)0.01398 (11)
H12A0.53860.8566−0.06110.017*
C130.75873 (9)0.81164 (9)−0.17369 (4)0.01315 (10)
C140.96900 (9)0.76806 (10)−0.20234 (4)0.01477 (11)
H14A1.02330.7606−0.26430.018*
C151.09656 (9)0.73581 (9)−0.13654 (4)0.01429 (11)
H15A1.23670.7074−0.15550.017*
C160.68663 (9)0.83005 (9)−0.32736 (4)0.01484 (11)
H16A0.76850.6985−0.34450.018*
H16B0.76800.9278−0.34650.018*
C170.49767 (11)0.87050 (11)−0.37121 (5)0.01895 (12)
H17A0.53580.8690−0.43660.028*
H17B0.41550.9986−0.35140.028*
H17C0.42170.7696−0.35360.028*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.01206 (19)0.0280 (3)0.0151 (2)−0.00354 (17)−0.00144 (15)−0.00028 (17)
O20.01199 (19)0.0265 (2)0.0186 (2)−0.00291 (17)−0.00501 (16)−0.00171 (18)
O30.01373 (19)0.0271 (3)0.01164 (19)−0.00273 (17)−0.00437 (14)0.00013 (16)
C10.0135 (2)0.0129 (2)0.0151 (2)−0.00301 (18)−0.00482 (18)0.00005 (18)
C20.0209 (3)0.0179 (3)0.0145 (2)−0.0041 (2)−0.0076 (2)0.00091 (19)
C30.0244 (3)0.0268 (3)0.0130 (2)−0.0054 (2)−0.0034 (2)0.0009 (2)
C40.0174 (3)0.0329 (4)0.0149 (3)−0.0044 (2)−0.0001 (2)0.0007 (2)
C50.0130 (2)0.0228 (3)0.0145 (2)−0.0035 (2)−0.00232 (19)0.0006 (2)
C60.0120 (2)0.0133 (2)0.0122 (2)−0.00281 (17)−0.00315 (17)0.00025 (17)
C70.0127 (2)0.0131 (2)0.0129 (2)−0.00335 (17)−0.00318 (17)0.00039 (17)
C80.0128 (2)0.0150 (2)0.0130 (2)−0.00247 (18)−0.00374 (18)−0.00015 (18)
C90.0138 (2)0.0146 (2)0.0129 (2)−0.00401 (18)−0.00363 (17)0.00107 (18)
C100.0129 (2)0.0128 (2)0.0116 (2)−0.00302 (17)−0.00291 (17)0.00046 (17)
C110.0136 (2)0.0159 (2)0.0113 (2)−0.00358 (18)−0.00181 (17)0.00037 (17)
C120.0124 (2)0.0167 (2)0.0125 (2)−0.00295 (18)−0.00149 (17)−0.00021 (18)
C130.0127 (2)0.0145 (2)0.0126 (2)−0.00236 (18)−0.00379 (17)0.00019 (18)
C140.0134 (2)0.0191 (3)0.0111 (2)−0.00229 (19)−0.00181 (17)−0.00019 (18)
C150.0122 (2)0.0177 (3)0.0124 (2)−0.00208 (18)−0.00191 (17)−0.00048 (18)
C160.0169 (2)0.0151 (2)0.0129 (2)−0.00269 (19)−0.00430 (18)0.00006 (18)
C170.0206 (3)0.0204 (3)0.0173 (3)−0.0031 (2)−0.0091 (2)0.0003 (2)

Geometric parameters (Å, °)

O1—C71.2491 (7)C9—C101.4543 (8)
O2—C11.3452 (8)C9—H9A0.93
O2—H1O20.928 (16)C10—C151.3998 (8)
O3—C131.3621 (7)C10—C111.4078 (8)
O3—C161.4334 (7)C11—C121.3791 (8)
C1—C21.4006 (9)C11—H11A0.93
C1—C61.4174 (8)C12—C131.4019 (8)
C2—C31.3803 (10)C12—H12A0.93
C2—H2A0.93C13—C141.3960 (8)
C3—C41.3993 (10)C14—C151.3957 (8)
C3—H3A0.93C14—H14A0.93
C4—C51.3868 (9)C15—H15A0.93
C4—H4A0.93C16—C171.5102 (9)
C5—C61.4053 (8)C16—H16A0.97
C5—H5A0.93C16—H16B0.97
C6—C71.4808 (8)C17—H17A0.96
C7—C81.4632 (8)C17—H17B0.96
C8—C91.3475 (8)C17—H17C0.96
C8—H8A0.93
C1—O2—H1O2105.5 (10)C15—C10—C9118.97 (5)
C13—O3—C16118.56 (5)C11—C10—C9123.04 (5)
O2—C1—C2117.49 (5)C12—C11—C10120.91 (5)
O2—C1—C6122.28 (5)C12—C11—H11A119.5
C2—C1—C6120.23 (6)C10—C11—H11A119.5
C3—C2—C1120.32 (6)C11—C12—C13120.33 (5)
C3—C2—H2A119.8C11—C12—H12A119.8
C1—C2—H2A119.8C13—C12—H12A119.8
C2—C3—C4120.34 (6)O3—C13—C14125.05 (5)
C2—C3—H3A119.8O3—C13—C12114.98 (5)
C4—C3—H3A119.8C14—C13—C12119.97 (5)
C5—C4—C3119.71 (6)C15—C14—C13119.03 (5)
C5—C4—H4A120.1C15—C14—H14A120.5
C3—C4—H4A120.1C13—C14—H14A120.5
C4—C5—C6121.34 (6)C14—C15—C10121.76 (5)
C4—C5—H5A119.3C14—C15—H15A119.1
C6—C5—H5A119.3C10—C15—H15A119.1
C5—C6—C1118.06 (5)O3—C16—C17106.17 (5)
C5—C6—C7122.80 (5)O3—C16—H16A110.5
C1—C6—C7119.14 (5)C17—C16—H16A110.5
O1—C7—C8120.46 (5)O3—C16—H16B110.5
O1—C7—C6118.86 (5)C17—C16—H16B110.5
C8—C7—C6120.67 (5)H16A—C16—H16B108.7
C9—C8—C7119.61 (5)C16—C17—H17A109.5
C9—C8—H8A120.2C16—C17—H17B109.5
C7—C8—H8A120.2H17A—C17—H17B109.5
C8—C9—C10127.21 (5)C16—C17—H17C109.5
C8—C9—H9A116.4H17A—C17—H17C109.5
C10—C9—H9A116.4H17B—C17—H17C109.5
C15—C10—C11117.98 (5)
O2—C1—C2—C3−179.69 (6)C7—C8—C9—C10−178.73 (5)
C6—C1—C2—C30.31 (10)C8—C9—C10—C15173.80 (6)
C1—C2—C3—C40.31 (11)C8—C9—C10—C11−7.18 (10)
C2—C3—C4—C5−0.43 (12)C15—C10—C11—C120.63 (9)
C3—C4—C5—C6−0.06 (11)C9—C10—C11—C12−178.39 (5)
C4—C5—C6—C10.65 (10)C10—C11—C12—C130.49 (9)
C4—C5—C6—C7179.82 (6)C16—O3—C13—C140.40 (9)
O2—C1—C6—C5179.22 (6)C16—O3—C13—C12−179.35 (5)
C2—C1—C6—C5−0.78 (9)C11—C12—C13—O3178.52 (5)
O2—C1—C6—C70.03 (9)C11—C12—C13—C14−1.24 (9)
C2—C1—C6—C7−179.97 (5)O3—C13—C14—C15−178.90 (6)
C5—C6—C7—O1−175.37 (6)C12—C13—C14—C150.83 (9)
C1—C6—C7—O13.79 (9)C13—C14—C15—C100.32 (10)
C5—C6—C7—C85.26 (9)C11—C10—C15—C14−1.04 (9)
C1—C6—C7—C8−175.59 (5)C9—C10—C15—C14178.03 (6)
O1—C7—C8—C93.15 (9)C13—O3—C16—C17179.71 (5)
C6—C7—C8—C9−177.48 (5)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O2,C1–C6 ring?
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O10.93 (2)1.66 (2)2.5113 (7)151 (1)
C16—H16A···Cg1i0.972.703.5762 (7)151
C16—H16B···Cg1ii0.972.663.5339 (7)151

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5143).

References

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