4-Hy­droxy-3-[(E)-3-phenyl­prop-2-eno­yl]-2H-chromen-2-one

Afef Ghouili; Rached Ben Hassen

doi:10.1107/S1600536811029801

. 2011 Jul 30;67(Pt 8):o2209. doi: 10.1107/S1600536811029801

4-Hydroxy-3-[(E)-3-phenylprop-2-enoyl]-2H-chromen-2-one

Afef Ghouili ^a, Rached Ben Hassen ^a,^*

PMCID: PMC3213638 PMID: 22091215

Abstract

In the title molecule, C₁₈H₁₂O₄, the phenyl ring is twisted by 23.2 (1)° from the mean plane of the chromene system. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules into zigzag chains extending in the [010] direction. An intramolecular O—H⋯O hydrogen bond is also present.

Related literature

For related structures, see: Traven et al. (2000 ▶); Sun & Cui (2008 ▶); Mechi et al. (2009 ▶); Hamdi et al. (2010 ▶); Asad et al. (2010 ▶). For the synthesis of coumarin chalcones, see: Claisen & Claparede (1881 ▶).

Experimental

Crystal data

C₁₈H₁₂O₄
M _r = 292.28
Monoclinic,
a = 11.8040 (5) Å
b = 3.8860 (5) Å
c = 29.7190 (5) Å
β = 97.164 (5)°
V = 1352.58 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.3 × 0.14 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: numerical (SADABS; Bruker, 2003 ▶) T _min = 0.861, T _max = 0.865
11154 measured reflections
2983 independent reflections
1404 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.300
S = 1.04
2983 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029801/cv5125sup1.cif

e-67-o2209-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029801/cv5125Isup2.hkl

e-67-o2209-Isup2.hkl^{(143.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029801/cv5125Isup3.cml

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
C5—H5⋯O3ⁱ	0.93	2.57	3.350 (5)	142
O1—H2⋯O2	0.99 (7)	1.51 (7)	2.413 (4)	149 (6)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Professor A. Ben Salah is acknowledged for his contribution to the X-ray diffraction data collection at the Laboratory of Materials Science and the Environment, University of Sfax, Tunisia.

supplementary crystallographic information

Comment

In continuation of our structural and biological studies of coumarin derivatives (Mechi et al., 2009; Hamdi et al., 2010), we present the crystal structure of the title compound (I) - a new chalcone of the coumarin.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related structures (Mechi et al., 2009; Asad et al., 2010). The presence of α, β-unsaturated ketone is indicated by the short O2–C10 and C11–C12 bond lengths of 1.289 (5)Å and 1.327 (5) Å, respectively, and the O2–C10–C11 and C10–C11–C12 bond angles of 118.2 (4) ° and 121.8 (4) °, respectively. The structure exhibits intramolecular hydrogen bonding between the hydroxyl oxygen and the ketonic oxygen in the coumarin group (Table 1). The chromen-2-one is twisted out of the plane of the phenyl ring (C13– C14) at 23.2 (1) °. The linkage between the coumarin system and phenyl ring is quite conjugated with bond lengths C10–C11 = 1.457 (5) Å, C11–C12 = 1.327 (5) Å, and C12–C13 = 1.440 (5) Å, suggesting that all non-hydrogen atoms between the electron-donors and acceptors are highly conjugated, leading to a π-bridge for the charge transfer from phenyl ring to coumarin system. Similar geometry has been observed in coumarin chalcone analogues (Mechi et al., 2009; Sun & Cui, 2008). Consequently, the C10–O2 = 1.289 (5) Å is elongated as compared with its mean value found in 3-acetyl-4hydroxycoumarin (1.253 Å) (Traven et al., 2000) owing to the localization of the hydroxyl hydrogen (H2) between the O2 ketonic oxygen and the hydroxyl oxygen O1. The O1–H2 distance (0.99 (7) Å) in (I) is shorter than that in related compounds - C₁₈H₁₀O₇ (1.22 (7) Å) (Mechi et al., 2009) and C₁₈H₁₀Cl₂O₄ (1.27 (2) Å) (Asad et al., 2010). It should be noted that the C9–O4 bond length (1.198 (5) Å) is less than that (1.210 Å) observed in 3-acetyl-4hydroxycoumarin (Traven et al., 2000). It was concluded that it was a substantial difference for stabilizing the H atom of the hydroxyl group when we changed the nature of the substituted R group (from H to Cl and to OCH3).

In the crystal structure, weak intermolecular C– H···O hydrogen bonds (Table 1) link molecules into zigzag chains extended in [010].

Experimental

The new chalcone (I) was synthesized using the Claisen Schmidt reaction (Claisen & Claparede, 1881), by the condensation of 3-acetyl-4hydroxycoumarin (1g, 4.9 mmol) and aromatic benzaldehyde (6.4 mmol, 0.5 ml) in chloroform (5 ml) in the presence of one drop of piperidine. The mixture was refluxed in a water bath for 2 h. After cooling at room temperature, a yellow solid was obtained in good yield, filtered, washed with ethanol, and dried in air. Yellow block-shaped single crystals of the title compound, suitable for X-ray structure determination, were recrystalized by slow evaporation of dichloromethane (CH₂Cl₂) at room temperature after several days. Yield: 1.1 g (80%). mp= 499K. IR: ν 3468 (OH), 1690(s) (>C=O), 1578 (C= C), 1272(s) (sym) (C-O-C); 1HNMR: δppm: 7.4-8.1 (m, 10H, Ar-H+ Hethyl), 16.1(s,1H,OH). 13C NMR (ppm): 192.6(CO); 181.56 (C2); 160.22 (C9); 100.8 (C8), 116.32-147.368 (C arom); 124.39 (Cethyl1), 154.79 (Cethyl2),