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; J Shashidhara Prasad

doi:10.1107/S1600536811007586

. 2011 Mar 9;67(Pt 4):o829. doi: 10.1107/S1600536811007586

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

G B Thippeswamy ^a, D Vijay Kumar ^b, B S Jayashree ^b, M A Sridhar ^a,^*, J Shashidhara Prasad ^a

PMCID: PMC3100019 PMID: 21754113

Abstract

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.

Related literature

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

Crystal data

C₁₇H₁₆O₃
M _r = 268.30
Monoclinic,
a = 11.340 (2) Å
b = 6.8350 (7) Å
c = 20.449 (4) Å
β = 117.710 (4)°
V = 1403.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.26 × 0.24 × 0.22 mm

Data collection

MacScience DIPLabo 32001 diffractometer
4137 measured reflections
2346 independent reflections
1502 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.184
S = 1.05
2346 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007586/jh2240sup1.cif

e-67-0o829-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007586/jh2240Isup2.hkl

e-67-0o829-Isup2.hkl^{(115.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O18—H18⋯O11	0.82	1.77	2.502 (3)	148
C13—H13⋯O18ⁱ	0.93	2.56	3.282 (3)	135

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Symmetry code: (i) Inline graphic .

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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.