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

S Sathya; D Reuben Jonathan; K Prathebha; G Usha; J Jovita

doi:10.1107/S1600536814008757

. 2014 Apr 26;70(Pt 5):o593–o594. doi: 10.1107/S1600536814008757

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

S Sathya ^a, D Reuben Jonathan ^b, K Prathebha ^a, G Usha ^a,^*, J Jovita ^a

PMCID: PMC4011235 PMID: 24860391

Abstract

In the title compound, C₁₆H₁₄O₄, there is an intramolecular O—H⋯O hydrogen bond. The benzene rings are inclined to one another by 13.89 (9)°. The prop-2-en-1-one group is twisted slightly, the O=C—C_ar—C_ar (ar = aromatic) and C=C—C=O torsion angles being −10.4 (3) and −7.4 (3)°, respectively. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming chains along [100]. These chains are further linked by O—H⋯O hydrogen bonds, forming corrugated sheets lying parallel to (010). There are C—H⋯π interactions present within the sheets.

Related literature

For the biological activity of chalcones and chalcone derivatives, see: Marais et al. (2005 ▶); Di Carlo et al. (1999 ▶); Troeberg et al. (2000 ▶); Ni et al. (2004 ▶). For a related structure, see: Jasinski et al. (2011 ▶). For the synthesis, see: Sidharthan et al. (2012 ▶); Chitra et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). graphic file with name e-70-0o593-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₄O₄
M _r = 270.27
Orthorhombic,
a = 16.2808 (8) Å
b = 10.4348 (5) Å
c = 16.2905 (7) Å
V = 2767.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.968, T _max = 0.977
12921 measured reflections
3441 independent reflections
1935 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.128
S = 1.05
3344 reflections
189 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 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/S1600536814008757/su2713sup1.cif

e-70-0o593-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008757/su2713Isup2.hkl

e-70-0o593-Isup2.hkl^{(160.8KB, hkl)}

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

Supporting information file. DOI: 10.1107/S1600536814008757/su2713Isup3.cml

CCDC reference: 991699

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

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

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3	0.86 (2)	2.20 (3)	2.655 (2)	113 (2)
O2—H2O⋯O1ⁱ	0.87 (2)	1.87 (2)	2.7349 (18)	173 (2)
O4—H4O⋯O1ⁱⁱ	0.86 (2)	2.22 (2)	2.937 (2)	141 (3)
C16—H16A⋯Cg ⁱⁱ	0.96	2.86	3.747 (3)	155

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

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 known as the precursors of all flavonoid type natural products in biosynthesis (Marais et al., 2005). They are a major class of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based food stuff and have been the subjects of interest for their significant pharmacological activities (Di Carlo et al., 1999). Many chalcones have been described for their high anti-malarial activity, probably as a result of addition of nucleophilic species to the double bond of the enone (Troeberg et al., 2000). A review of anti-infective and anti-inflammatory chalcones and recent advances in therapeutic chalcones have been reported (Ni et al., 2004). To understand the three dimensional features of this class of compounds, we report herein on the crystal structure of the title compound.

The molecular structure of the title molecule is illustrated in Fig. 1. The bond lengths (Allen et al., 1987) and bond angles are within normal values. The bond angles C6—C7—C8 = 119.12 (14) ° and C8═C9—C10 = 127.20 (17) ° are comparable with those in a similar reported structure (E)-3-(3,4-Dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (2E)-3-(3,4-Dimethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (Jasinski et al., 2011). This may be due to the presence of the keto group and associated steric forces. The prop-2-en-1-one group is twisted slightly with torsion angles O1═C7—C8—C9 and C5—C6—C7═O1 being -10.4 (3) and -7.4 (3) °, respectively. These values are comparable with the value of -6.9 (2) and -15.9 (2) ° reported for the above mentioned structure.

In the crystal, molecules are linked by O—H···O hydrogen bonds forming chains propagating along the a axis (Table 1 and Fig. 2). These chains are linked by further O—H···O hydrogen bonds forming corrugated sheets lying parallel to (010). Within the sheets there are C—H···π interactions present (Table 1). In total each molecule is linked to four neighbours by O—H···O hydrogen bonds (Table 1 and Fig. 2). Atom O4 acts as a bifurcated donor forming intra- and inter-molecular O—H···O hydrogen bonds (Table 1 and Fig. 2).

2. Experimental

The title compound was synthesized by a published procedure using the acid catalyzed Claisen-Schmidt reaction (Sidharthan et al., 2012; Chitra et al., 2013) Dry HCl gas was passed through a well cooled and stirred solution of 4-hydroxyacetophenone (0.02 mol) and vanillin (0.02 mol) in 125 ml of dry ethanol, placed in a 250 ml round-bottomed flask, for about 1 h. A wine-red coloured solution was formed to which ice cold water was added. Yellow block-like crystals of the title compound separated and were washed with double distilled water and re-crystallized from hot ethanol (Yield 85%; M.p. 454 K).