(2E)-1-(3,5-Di­hydroxy­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one

K S Ezhilarasi; D Reuben Jonathan; Shanmugam Sathya; K Prathebha; G Usha

doi:10.1107/S1600536814009155

. 2014 Apr 26;70(Pt 5):o608–o609. doi: 10.1107/S1600536814009155

(2E)-1-(3,5-Dihydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

K S Ezhilarasi ^a, D Reuben Jonathan ^b, Shanmugam Sathya ^a, K Prathebha ^a, G Usha ^a,^*

PMCID: PMC4011220 PMID: 24860401

Abstract

In the title compound, C₁₆H₁₄O₄, the benzene rings are inclined to one another by 4.91 (7)°. The conformation about the C=O and C=C bonds is trans and cis, respectively. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming inversion dimers with an R ₂ ²(14) ring motif. The dimers are linked via O—H⋯O and C—H⋯O hydrogen bonds, forming undulating two-dimensional networks lying parallel to (10-1). These networks are linked by further C—H⋯O hydrogen bonds, forming a three-dimensional structure.

Related literature

For the biological activity of chalcone derivatives, see: Shenvi et al. (2013 ▶); Sharma et al. (2012 ▶); Hsieh et al. (2012 ▶); Sashidhara et al. (2011 ▶). For related structures, see: Ahn et al. (2013 ▶); Jasinski et al. (2011 ▶). For standard bend lengths, see: Allen et al. (1987 ▶). For the synthesis, see: Shettigar et al. (2006 ▶); Patil et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). graphic file with name e-70-0o608-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₄O₄
M _r = 270.28
Monoclinic,
a = 9.1920 (9) Å
b = 13.8931 (13) Å
c = 10.9299 (10) Å
β = 106.619 (2)°
V = 1337.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.979, T _max = 0.981
13378 measured reflections
3402 independent reflections
2617 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.137
S = 0.91
3384 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814009155/su2727sup1.cif

e-70-0o608-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009155/su2727Isup2.hkl

e-70-0o608-Isup2.hkl^{(162.6KB, hkl)}

Click here for additional data file.^{(5.3KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814009155/su2727Isup3.cml

CCDC reference: 998945

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.90	2.7196 (15)	174
O3—H3A⋯O2ⁱⁱ	0.82	2.03	2.8361 (14)	167
C3—H3⋯O2ⁱⁱ	0.93	2.59	3.2875 (17)	132
C5—H5⋯O1ⁱ	0.93	2.43	3.1498 (17)	134
C12—H12⋯O4ⁱⁱⁱ	0.93	2.47	3.3926 (16)	169

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.

supplementary crystallographic information

1. Comment

Chalcones are one of the secondary metabolites in plants and belong to a class of flavonoid. They have shown diverse biological activities including anticancer (Shenvi et al., 2013), antimicrobial (Sharma et al. 2012), antidiabetic (Hsieh et al., 2012) and antiinflammatory (Sashidhara et al., 2011). As part of our attempt to investigate how the substituent effects of chalcones effect the biological activities of various compounds, the title compound was synthesized and its crystal structure is reported herein.

The molecuar structure of the title compound is illustrated in Fig. 1. The bond lengths (Allen et al., 1987) and bond angles are within normal values. The benzene rings (C1-C6 and C10-C15) are inclined to one another by 4.91 (7) °. The torsion angles about the C7═O1 and C8═C9 bonds confirm the trans and cis conformations of the respective bonds. The C8═ C9 bond distance is 1.332 (2) Å, and is in good agreement with the value [1.329 (3) Å] reported for a similar structure (Ahn et al., 2013). The methoxy C atom and hydroxy O atoms are almost coplanar with the benezene ring to which they are attached. The bond angles C4—C7—C8 = 120.4 (1)° and C8—C9—C10 = 128.2 (1)° differ slightly from the normal values but are comparable with the values reported for a similar structure (Jasinski et al., 2011).

In the crystal, molecules are linked by O—H···O hydrogen bonds forming inversion dimers with a graph set motif of R²₂(14) [Bernstein et al., 1995]. The dimers are linked by O-H···O and C-H···O hydrogen bonds forming undulating two-dimensional networks lying parallel to (10-1) [Fig. 2 and Table 1]. These networks are linked by further C-H···O hydrogen bonds forming a three-dimensional structure (Table 1).

2. Experimental

The title compound was syntheized by the base catalyzed Claisen-Schmidt reaction according to the published procedures (Shettigar et al., 2006; Patil et al., 2007). In a 250 ml round-bottomed flask 3,5-hydroxyacetophenone (0.05 mol) and 4-methoxybenzaldehyde (0.05 mol) were placed and 120 ml of absolute alcohol were added. The mixture was stirred at room temperature for 5 min. Then 20 ml of 20% sodium hydroxide solution was added and the mixture was stirred for 2 h. The precipitate generated by adding a sufficient amount of dilute hydrochloric acid was filtered, washed with water and dried. The crude product was recrystallized twice from absolute alcohol yielding colourless block-like crystals (Yield 79%; M.p. 477 K).