3-[(E)-3-(2,4-Dichloro­phen­yl)prop-2-en­oyl]-4-hy­droxy-2H-chromen-2-one

Mohammad Asad; Chuan-Wei Oo; Hasnah Osman; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S1600536810043837

. 2010 Oct 31;66(Pt 11):o3022–o3023. doi: 10.1107/S1600536810043837

3-[(E)-3-(2,4-Dichlorophenyl)prop-2-enoyl]-4-hydroxy-2H-chromen-2-one

Mohammad Asad ^a, Chuan-Wei Oo ^a,^‡, Hasnah Osman ^a, Ching Kheng Quah ^b,^§, Hoong-Kun Fun ^b,^*,^¶

PMCID: PMC3009251 PMID: 21589179

Abstract

In the title compound, C₁₈H₁₀Cl₂O₄, the chromen-2-one ring system is almost planar [maximum deviation = 0.028 (1) Å] and is inclined at an angle of 16.35 (4)° with respect to the benzene ring. The C=C bond has an E configuration. The molecular conformation is stabilized by an almost symmetric intramolecular O⋯H⋯O hydrogen bond and a C—H⋯O interaction, both of which form S(6) ring motifs. In the crystal structure, molecules are linked into sheets lying parallel to (100) via intermolecular C—H⋯O hydrogen bonds. The crystal packing is further consolidated by π–π stacking interactions [centroid-to-centroid separation = 3.6615 (6) Å].

Related literature

For general background to and the biological activity of chalcones, see: Claisen et al. (1881 ▶); Siddiqui et al. (2008 ▶); Harborne & Mabry (1982 ▶); Bandgar et al. (2010 ▶). For related structures, see: Arshad et al. (2010 ▶); Asad et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₈H₁₀Cl₂O₄
M _r = 361.16
Monoclinic,
a = 4.5233 (2) Å
b = 21.2099 (9) Å
c = 15.6304 (7) Å
β = 91.607 (1)°
V = 1498.97 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.857, T _max = 0.959
25117 measured reflections
6698 independent reflections
5270 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.101
S = 1.05
6698 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043837/hb5700sup1.cif

e-66-o3022-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043837/hb5700Isup2.hkl

e-66-o3022-Isup2.hkl^{(327.8KB, 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
O3—H1O⋯O4	1.27 (2)	1.17 (2)	2.3947 (11)	156 (2)
C11—H11A⋯O2	0.93	2.29	2.8704 (12)	120
C4—H4A⋯O4ⁱ	0.93	2.45	3.2514 (13)	144
C17—H17A⋯O1ⁱⁱ	0.93	2.54	3.3966 (13)	154

Open in a new tab

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

Acknowledgments

The authors are grateful to Universiti Sains Malaysia (USM) for providing the necessary research facilities and RU research funding under grant No. 1001/PKIMIA/811134. HKF and CKQ thank USM for Research University Grant No. 1001/PFIZIK/811160. MA thanks USM for the award of a postdoctoral fellowship. CKQ thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

Chalcones are generally prepared from aldehydes and methyl ketones under basic conditions by applying the Claisen–Schmidt condensation (Claisen et al., 1881; Siddiqui et al., 2008). A large number of chalcones and their derivatives are found in natural and synthetic products and are also biogenetically precursors of known flavonoids, isoflavonoids (Harborne & Mabry, 1982) which exhibited a potential variety of biological activities (Bandgar et al., 2010).

In the title molecule, (I), (Fig. 1), the chromen-2-one (O1/C1–C9) ring system is nearly planar (maximum deviation = 0.028 (1) Å for atom C1) and is inclined at an angle of 16.35 (4) ° with the phenyl ring (C13–C18). The C11═C12 bond has an E configuration. The molecule is stabilized by intramolecular O3—H1O···O4 and C11—H11A···O2 hydrogen bonds, which form S(6) ring motifs (Bernstein et al., 1995). Bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable with the related structures (Arshad et al., 2010; Asad et al., 2010).

In the crystal packing (Fig. 2), the molecules are linked into two-dimensional sheets parallel to (100) via intermolecular C4—H4A···O4 and C17—H17A···O1 hydrogen bonds (Table 1). Short intermolecular distances [3.6615 (6) Å] between symmetry-related O1/C1/C2/C7–C9 (centroid Cg1) and C2–C7 (centroid Cg2) rings [symmetry code: -1+x, y, z] indicate the existence of π–π stacking interactions.

Experimental

To a stirred solution of 3-acetyl-4-hydroxycoumarin (0.98 mmol, 200 mg) in ethyl alcohol (10 ml), 2,4-dichlorobenzaldehyde (0.98 mmol, 171 mg) was added in the presence of one drop of piperidine. The mixture was refluxed on water bath for 14 h. After cooling at room temperature, a yellow solid was obtained, filtered, washed with ethanol–water, dried and recrystallized from chloroform as shining yellow needles of (I) in 70% yield.