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Acta Cryst. (2011). E67, o829    [ doi:10.1107/S1600536811007586 ]

1-(2-Hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one

G. B. Thippeswamy, D. Vijay Kumar, B. S. Jayashree, M. A. Sridhar and J. Shashidhara Prasad

Abstract top

The molecule of the title compound, C17H16O3, exists in the E conformation with respect to the central C=C bond, is almost planar(r.m.s. deviation = 0.003 Å) and has an intramolecular O-H...O hydrogen bond, which generates an S(6) ring. In the crystal, molecules are linked by C-H...O interactions.

Comment top

Chalcones (1,3-diarylpropenones) are well known intermediates for the synthesis of various heterocyclic compounds. The compounds with chalcone backbone have been reported to possess various biological activities such as anti-oxidant (Jayashree et al., 2009), anti-inflammatory (Hsieh et al., 2000), anti-cancer (Epifano et al., 2007), anti-hyperglycemic (Satyanarayana et al., 2004), anti-viral (Onyilagna et al., 1997), anti-leishmanial (Nielsen et al.,1995), anti-tubercular (Siva Kumar et al., 2007), immunomodulatory (Barford et al., 2002), inhibition of various enzymes like leukotriene B (Deshpande et al., 1999), tyrosinase kinase (Khatib et al., 2005) and aldose reductase (Severi et al., 1998) etc. The presence of a reactive alph, beta-unsaturated ketone function in chalcones is found to be responsible for their activity. In the present communication, we report the synthesis and crystal structure of substituted 2-hydroxy-chalcone. In the title compound, C17H16O3, the dihedral angle between the ring systems is 9.57 (13)°. The central prop-2-en-1-oneunit is planar (r.m.s. deviation = 0.003 Å) and is oriented at a dihedral angle of 2.46 (10)° with respect to the methoxyphenyl ring and at 7.46 (10)° with respect to the methylphenyl ring. The angles C2—C1—O11, C12—C1—O11 and C2—C1—C12 are 118.5 (3)°, 119.9 (2)° and 121.5 (2)° respectively which indicate that the position of C1 atom is nearly in trigonal geometry. The bond lengths and bond angles of the molecule are comparable with the values reported for 1-(2-hydroxy-5-methylphenyl)-3-(3-methylthiophen-2-yl) prop-2-en-1-one (Thippeswamy et al.,2010). The atoms C4, C7 in methylphenyl ring deviate by -0.018 (2) Å, -0.014 (3) Å, and the atoms C12, C15 in methoxyphenyl ring deviate by -0.002 (2) Å, -0.003 (3)Å respectively from Cremer and Pople plane (Cremer et al.,1975) which show that the two six-membered rings are in planar conformation. The packing of the molecules is characterized by intramolecular hydrogen bond of type O–H–O.

Related literature top

For the biological activity of compounds with a chalcone backbone, see: Jayashree et al. (2009); Epifano et al. (2007); Onyilagna et al. (1997); Satyanarayana et al. (2004); Deshpande et al. (1999); Hsieh et al. (2000); Khatib et al. (2005); Barford et al. (2002); Nielsen et al. (1995); Severi et al. (1998); Siva Kumar et al. (2007). For a related structure, see: Thippeswamy et al. (2010). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared by dissolving 2-hydroxy-4- methoxyacetophenone 0.05 m mol in 15 ml of ethanol taken in a conical flask. To this 5 ml of 20° aqueous sodium hydroxide was added and kept for stirring at room temperature. To this mixture, 4-methylbenzaldehyde 0.05 m mol was added and continued stirring till the completion of reaction. The progress of the reaction was monitored by TLC using n-hexane and ethyl acetate as solvent system. After completion of the reaction, the mixture was poured into ice cold water, mixed properly and acidified with dilute hydrochloric acid. The title compound separates as precipitate which was collected by filtration and crystallized from methanol. The compound was chafacterized by spectroscope technique. The IR spectrum was recorded in KBr on FTIR-8400 (Shimadzu). The 1H NMR spectrum was recorded in CdCl3 solution at 400 MHz on AMX 400 MHz High Resolution Multinuclear FT-NMR Spectrometer (Bruker) with tetramethylsilane (TMS) as internal standard.

Computing details top

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Crystal structure of the title compound with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the b axis.
1-(2-Hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one top
Crystal data top
C17H16O3F(000) = 568
Mr = 268.30Dx = 1.270 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4137 reflections
a = 11.340 (2) Åθ = 2.2–25.0°
b = 6.8350 (7) ŵ = 0.09 mm−1
c = 20.449 (4) ÅT = 293 K
β = 117.710 (4)°Block, yellow
V = 1403.2 (4) Å30.26 × 0.24 × 0.22 mm
Z = 4
Data collection top
MacScience DIPLabo 32001
diffractometer		1502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 25.0°, θmin = 2.2°
Detector resolution: 10.0 pixels mm-1h = −13→13
ω scansk = −7→7
4137 measured reflectionsl = −24→24
2346 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.184 w = 1/[σ2(Fo2) + (0.1052P)2 + 0.0529P]
S = 1.05(Δ/σ)max = 0.010
2346 reflectionsΔρmax = 0.15 e Å−3
184 parametersΔρmin = −0.15 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (8)
Crystal data top
C17H16O3V = 1403.2 (4) Å3
Mr = 268.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.340 (2) ŵ = 0.09 mm−1
b = 6.8350 (7) ÅT = 293 K
c = 20.449 (4) Å0.26 × 0.24 × 0.22 mm
β = 117.710 (4)°
Data collection top
MacScience DIPLabo 32001
diffractometer		1502 reflections with I > 2σ(I)
4137 measured reflectionsRint = 0.029
2346 independent reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.184Δρmax = 0.15 e Å−3
S = 1.05Δρmin = −0.15 e Å−3
2346 reflectionsAbsolute structure: ?
184 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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) top
xyzUiso*/Ueq
O110.22698 (19)0.0248 (2)0.50576 (11)0.1003 (8)
O180.4503 (2)0.1776 (2)0.58182 (12)0.1010 (8)
O190.82822 (19)−0.2381 (3)0.68536 (10)0.0952 (8)
C10.2778 (3)−0.1418 (3)0.51232 (13)0.0769 (9)
C20.1894 (3)−0.3084 (4)0.47598 (14)0.0781 (9)
C30.0588 (3)−0.2910 (4)0.44711 (13)0.0788 (9)
C4−0.0439 (2)−0.4376 (4)0.40885 (12)0.0745 (9)
C5−0.0165 (3)−0.6329 (4)0.40093 (13)0.0771 (9)
C6−0.1187 (3)−0.7615 (4)0.36199 (14)0.0829 (10)
C7−0.2504 (3)−0.7042 (4)0.33000 (13)0.0853 (10)
C8−0.2767 (3)−0.5123 (5)0.34017 (15)0.0941 (11)
C9−0.1758 (3)−0.3830 (4)0.37904 (14)0.0876 (10)
C10−0.3608 (3)−0.8452 (5)0.28614 (16)0.1111 (14)
C120.4201 (2)−0.1668 (3)0.55578 (12)0.0695 (8)
C130.4837 (3)−0.3491 (3)0.56897 (14)0.0777 (9)
C140.6169 (3)−0.3701 (3)0.61167 (14)0.0833 (10)
C150.6964 (3)−0.2045 (4)0.64370 (14)0.0771 (9)
C160.6383 (3)−0.0211 (3)0.63231 (14)0.0775 (10)
C170.5025 (3)−0.0035 (3)0.58930 (13)0.0735 (9)
C200.9130 (3)−0.0751 (4)0.71775 (17)0.1034 (12)
H20.22610−0.428000.473300.0940*
H30.02810−0.168300.451800.0950*
H50.07130−0.676200.422100.0920*
H6−0.09840−0.890800.357100.0990*
H8−0.36460−0.470100.320200.1130*
H9−0.19680−0.255300.385500.1050*
H10A−0.42770−0.838000.302300.1670*
H10B−0.32560−0.975700.293400.1670*
H10C−0.39960−0.812200.234700.1670*
H130.43250−0.459800.547700.0930*
H140.65550−0.493600.619700.1000*
H160.690400.089000.653400.0930*
H180.369500.172600.555500.1510*
H20A0.906000.013400.679600.1550*
H20B1.00340−0.119300.745000.1550*
H20C0.88710−0.009100.750500.1550*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0982 (14)0.0672 (11)0.1254 (16)0.0151 (9)0.0435 (12)0.0038 (10)
O180.1048 (15)0.0578 (10)0.1353 (16)0.0064 (9)0.0516 (12)0.0001 (9)
O190.0834 (14)0.0929 (13)0.1058 (14)0.0051 (10)0.0411 (11)−0.0085 (10)
C10.0879 (18)0.0692 (14)0.0771 (15)0.0051 (12)0.0414 (14)0.0029 (11)
C20.0831 (18)0.0705 (14)0.0819 (16)0.0012 (12)0.0393 (13)−0.0014 (11)
C30.0831 (19)0.0788 (15)0.0731 (15)0.0096 (13)0.0352 (14)0.0036 (12)
C40.0741 (17)0.0851 (16)0.0634 (14)0.0081 (12)0.0313 (12)0.0052 (11)
C50.0742 (16)0.0832 (16)0.0737 (15)0.0129 (12)0.0343 (13)0.0039 (12)
C60.0848 (19)0.0857 (16)0.0788 (16)−0.0035 (14)0.0385 (14)−0.0054 (13)
C70.0818 (19)0.1053 (19)0.0654 (15)−0.0058 (15)0.0314 (13)0.0042 (13)
C80.0705 (17)0.114 (2)0.0881 (18)0.0105 (15)0.0288 (14)0.0126 (16)
C90.0760 (18)0.0920 (17)0.0909 (18)0.0163 (14)0.0355 (15)0.0095 (14)
C100.096 (2)0.141 (3)0.0857 (19)−0.0278 (19)0.0334 (16)−0.0083 (18)
C120.0817 (17)0.0599 (12)0.0743 (14)0.0020 (11)0.0426 (13)0.0004 (10)
C130.0884 (18)0.0621 (13)0.0843 (16)0.0032 (11)0.0415 (14)−0.0045 (11)
C140.096 (2)0.0649 (14)0.0892 (17)0.0089 (12)0.0433 (15)−0.0031 (12)
C150.0809 (18)0.0813 (15)0.0758 (15)0.0040 (13)0.0420 (14)−0.0022 (12)
C160.0836 (19)0.0677 (14)0.0885 (17)−0.0030 (12)0.0461 (15)−0.0061 (12)
C170.0923 (19)0.0577 (13)0.0832 (15)0.0049 (11)0.0514 (14)0.0018 (11)
C200.087 (2)0.112 (2)0.107 (2)−0.0097 (17)0.0417 (17)−0.0209 (17)
Geometric parameters (Å, °) top
O11—C11.255 (3)C14—C151.405 (4)
O18—C171.350 (3)C15—C161.385 (4)
O19—C151.352 (4)C16—C171.378 (5)
O19—C201.419 (4)C2—H20.9300
O18—H180.8200C3—H30.9300
C1—C21.470 (4)C5—H50.9300
C1—C121.445 (4)C6—H60.9300
C2—C31.320 (5)C8—H80.9300
C3—C41.458 (4)C9—H90.9300
C4—C91.379 (4)C10—H10A0.9600
C4—C51.397 (4)C10—H10B0.9600
C5—C61.375 (4)C10—H10C0.9600
C6—C71.380 (5)C13—H130.9300
C7—C81.382 (4)C14—H140.9300
C7—C101.502 (4)C16—H160.9300
C8—C91.370 (5)C20—H20A0.9600
C12—C171.412 (3)C20—H20B0.9600
C12—C131.402 (3)C20—H20C0.9600
C13—C141.356 (5)
O11···O182.502 (3)H2···C52.8200
O18···O112.502 (3)H2···C132.7100
O18···C13i3.282 (3)H2···H52.3100
O11···H32.3900H2···H132.1300
O11···H9ii2.8700H3···O112.3900
O11···H5i2.7200H3···H92.3400
O11···H181.7700H5···O11v2.7200
O18···H13i2.5600H5···C22.8200
C1···C7iii3.540 (4)H5···H22.3100
C3···C5iii3.398 (4)H6···H10B2.3600
C3···C4iii3.551 (4)H8···H10A2.5900
C4···C4iii3.488 (3)H8···C10viii2.9800
C4···C3iii3.551 (4)H9···H32.3400
C5···C3iii3.398 (4)H9···O11ii2.8700
C6···C20iv3.590 (5)H10A···H82.5900
C7···C1iii3.540 (4)H10A···C12iii2.8600
C10···C12iii3.596 (4)H10A···C17iii2.9200
C12···C10iii3.596 (4)H10B···H62.3600
C13···O18v3.282 (3)H13···O18v2.5600
C20···C6iv3.590 (5)H13···C22.6600
C1···H182.3700H13···H22.1300
C2···H132.6600H16···C202.5000
C2···H52.8200H16···H20A2.3100
C4···H20Cvi2.9800H16···H20C2.2900
C5···H22.8200H18···O111.7700
C5···H20Cvi2.9100H18···C12.3700
C6···H20Cvi2.9600H20A···C162.7300
C7···H20Cvi3.0900H20A···H162.3100
C10···H8vii2.9800H20C···C162.7300
C12···H10Aiii2.8600H20C···H162.2900
C13···H22.7100H20C···C4ix2.9800
C16···H20A2.7300H20C···C5ix2.9100
C16···H20C2.7300H20C···C6ix2.9600
C17···H10Aiii2.9200H20C···C7ix3.0900
C20···H162.5000
C15—O19—C20118.1 (2)C3—C2—H2119.00
C17—O18—H18109.00C2—C3—H3116.00
O11—C1—C2118.5 (3)C4—C3—H3116.00
O11—C1—C12119.9 (2)C4—C5—H5120.00
C2—C1—C12121.5 (2)C6—C5—H5120.00
C1—C2—C3121.1 (3)C5—C6—H6119.00
C2—C3—C4128.9 (3)C7—C6—H6119.00
C3—C4—C9118.9 (3)C7—C8—H8119.00
C5—C4—C9117.5 (3)C9—C8—H8119.00
C3—C4—C5123.6 (3)C4—C9—H9119.00
C4—C5—C6120.3 (3)C8—C9—H9119.00
C5—C6—C7121.9 (3)C7—C10—H10A110.00
C6—C7—C8117.4 (3)C7—C10—H10B109.00
C6—C7—C10121.3 (3)C7—C10—H10C109.00
C8—C7—C10121.4 (3)H10A—C10—H10B109.00
C7—C8—C9121.3 (3)H10A—C10—H10C109.00
C4—C9—C8121.6 (3)H10B—C10—H10C109.00
C1—C12—C13123.4 (2)C12—C13—H13119.00
C1—C12—C17120.2 (2)C14—C13—H13119.00
C13—C12—C17116.4 (2)C13—C14—H14120.00
C12—C13—C14122.5 (2)C15—C14—H14120.00
C13—C14—C15119.8 (2)C15—C16—H16120.00
O19—C15—C16124.1 (3)C17—C16—H16120.00
C14—C15—C16119.9 (3)O19—C20—H20A109.00
O19—C15—C14116.0 (3)O19—C20—H20B109.00
C15—C16—C17119.3 (2)O19—C20—H20C110.00
O18—C17—C16117.0 (2)H20A—C20—H20B109.00
C12—C17—C16122.1 (2)H20A—C20—H20C110.00
O18—C17—C12120.9 (3)H20B—C20—H20C109.00
C1—C2—H2119.00
C20—O19—C15—C16−1.9 (4)C5—C6—C7—C10178.6 (3)
C20—O19—C15—C14178.8 (3)C10—C7—C8—C9−178.8 (3)
C12—C1—C2—C3168.4 (3)C6—C7—C8—C91.5 (4)
O11—C1—C12—C13176.6 (3)C7—C8—C9—C40.9 (4)
C2—C1—C12—C13−2.5 (4)C17—C12—C13—C140.2 (4)
C2—C1—C12—C17179.3 (3)C1—C12—C13—C14−178.0 (3)
O11—C1—C12—C17−1.7 (4)C13—C12—C17—O18−178.0 (2)
O11—C1—C2—C3−10.7 (4)C13—C12—C17—C160.4 (4)
C1—C2—C3—C4179.5 (2)C1—C12—C17—O180.4 (4)
C2—C3—C4—C9−176.0 (3)C1—C12—C17—C16178.8 (3)
C2—C3—C4—C54.5 (4)C12—C13—C14—C15−0.9 (4)
C3—C4—C5—C6−177.9 (3)C13—C14—C15—C160.8 (4)
C5—C4—C9—C8−2.9 (4)C13—C14—C15—O19−179.9 (3)
C9—C4—C5—C62.6 (4)O19—C15—C16—C17−179.4 (3)
C3—C4—C9—C8177.6 (3)C14—C15—C16—C17−0.2 (4)
C4—C5—C6—C7−0.4 (4)C15—C16—C17—O18178.0 (3)
C5—C6—C7—C8−1.7 (4)C15—C16—C17—C12−0.5 (4)
Symmetry codes: (i) x, y+1, z; (ii) −x, −y, −z+1; (iii) −x, −y−1, −z+1; (iv) −x+1, −y−1, −z+1; (v) x, y−1, z; (vi) x−1, −y−1/2, z−1/2; (vii) −x−1, y−1/2, −z+1/2; (viii) −x−1, y+1/2, −z+1/2; (ix) x+1, −y−1/2, z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O18—H18···O110.821.772.502 (3)148
C3—H3···O110.932.392.758 (3)103
C13—H13···O18v0.932.563.282 (3)135
Symmetry codes: (v) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O18—H18···O110.821.772.502 (3)148
C13—H13···O18i0.932.563.282 (3)135
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

The authors are grateful to the DST/CSIR, New Delhi, for financial support under projects SP/I2/FOO/93 and 01/1904/03/EMR-II 2004. The authors duly acknowledge Manipal College of Pharmaceutical Sciences, Manipal, for providing facilities to carry out the synthetic work.

references
References top

Barford, L., Kemp, K., Hansen, M. & Kharazmi, A. (2002). Int. Immunopharmacol. 2, 545–550.

Cremer, D. J. A. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Deshpande, A. M., Argade, N. P., Eckman, J. & Natu, A. A. (1999). Bioorg. Med. Chem. 7, 1237–1240.

Epifano, F., Genovese, S., Menghini, L. & Curini, M. (2007). Phytochemistry, 68, 939–953.

Hsieh, H. K., Tsao, L. T. & Wang, J. P. (2000). J. Pharm. Pharmacol. 52, 163–171.

Jayashree, B. S., Shakeela, Y. & Vijay Kumar, D. (2009). Asian J. Chem. 21, 5918–5922.

Johnson, C. K. (1976). ORTEPII. Report ORNL–5138. Oak Ridge National Laboratory, Tennessee, USA.

Khatib, S., Nerya, O., Musa, R., Tamir, S. & Vaya, J. (2005). Bioorg. Med. Chem. 13, 433–441.

MacScience (2002). XPRESS. MacScience Corporation, Tokyo, Japan.

Nielsen, S. F., Chen, M., Theander, T. G. A., Kharazmi, A. & Christensen, S. B. (1995). Bioorg. Med. Chem. Lett. 5, 449–452.

Onyilagna, J. C., Malhotra, B., Elder, M. & Towers, G. H. N. (1997). Can. J. Plant Pathol. 19, 133–137.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Satyanarayana, M., Priti, T., Tripathi, K., Ram, P. & Srivastava, A. K. (2004). Bioorg. Med. Chem. 12, 883–889.

Severi, F., Benvenuti, S., Costantino, L., Vampa, G., Melegari, M. & Antolini, L. (1998). Eur. J. Med. Chem. 33, 859–866.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siva Kumar, P. M., Geetha Babu, S. K. & Mukesh, D. (2007). Chem. Pharm. Bull. 55, 44–49.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Thippeswamy, G. B., Vijay Kumar, D., Jayashree, B. S., Sridhar, M. A. & Shashidhara Prasad, J. (2010). Acta Cryst. E66, o1385.