(E)-3-(2,6-Dichloro­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

Lotfi Benmekhbi; Ratiba Belhouas; Sofiane Bouacida; Salima Mosbah; Leila Bencharif

doi:10.1107/S1600536809020145

. 2009 Jun 6;65(Pt 7):o1472–o1473. doi: 10.1107/S1600536809020145

(E)-3-(2,6-Dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

Lotfi Benmekhbi ^a, Ratiba Belhouas ^b,^*, Sofiane Bouacida ^c, Salima Mosbah ^d, Leila Bencharif ^d

PMCID: PMC2969433 PMID: 21582775

Abstract

In the title compound, C₁₆H₁₂Cl₂O₂, the dichlorophenyl and methoxyphenyl groups are linked by a prop-2-en-1-one group. The C=C double bond is trans configured. The molecule is not planar, as can be seen from the dihedral angle of 6.21 (7)° between the planes of the two rings. The crystal structure can be described by two types of crossed layers which are parallel to (110) and (1 Inline graphic 0).

Related literature

For background to the applications of chalcones, see: Liu et al. (2003 ▶); Li et al. (1995 ▶); Hsieh et al. (1998 ▶); Barford et al. (2002 ▶); Rojas et al. (2002 ▶); Nerya et al. (2006 ▶); Yang et al. (2000 ▶); Ducki et al. (1998 ▶); Goto et al. (1991 ▶); Indira et al. (2002 ▶); Lawrence et al. (2001 ▶); Nielsen et al. (2005 ▶); Sarker & Nahar (2004 ▶); Sarojini et al. (2006 ▶). For related structures, see: Yathirajan et al. (2007 ▶); Butcher et al. (2007 ▶); Fischer et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₂Cl₂O₂
M _r = 307.16
Orthorhombic,
a = 6.4793 (2) Å
b = 12.9807 (5) Å
c = 16.7819 (8) Å
V = 1411.46 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 100 K
0.37 × 0.28 × 0.2 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS, Bruker, 1998 ▶) T _min = 0.824, T _max = 0.913
6643 measured reflections
3211 independent reflections
2964 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.090
S = 1.05
3211 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 1331 Friedel pairs
Flack parameter: 0.01 (6)

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020145/bq2141sup1.cif

e-65-o1472-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020145/bq2141Isup2.hkl

e-65-o1472-Isup2.hkl^{(154.3KB, 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
C4—H4⋯Cg1ⁱ	0.95	2.84	3.727	157
C7—H7⋯Cg2ⁱ	0.95	2.85	3.360	115

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Symmetry code: (i) Inline graphic . Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

Acknowledgments

The authors are grateful to Dr Thierry Roisnel, Centre de Diffractométrie X (CDIFX) de Rennes, Université de Rennes 1, France, for the data-collection facilities.

supplementary crystallographic information

Comment

For a structurally simple group of compounds, chalcones have displayed an impressive array for biological activities, among which anti-malarial (Liu et al., 2003), anti protozoal (Li et al., 1995), anti-inflammatory (Hsieh et al., 1998), immunomodulatory (Barford et al., 2002), nitric oxid inhibition (Rojas et al., 2002), tyronase inhibition (Nerya et al., 2006), cytotoxic (Yang et al., 2000) and anticancer (Ducki et al., 1998) activities have been cited in literature.

Chalcone may be useful for the chemotherapy of leishmanisis among others (Lawrence et al., 2001), they are also used as antibiotics (Nielsen et al., 2005). They were synthesized by a base catalyzed Claisen-Schmidt condensation of aromatic aldehydes and ketones. A natural medicine genus Angelica is known to contain large number of naturally occurring chalcones (Sarker et al., 2004). Chalcone derivatives are recognized for NLO properties and have good crystallization ability (Goto et al., 1991; Indira et al., 2002; Sarojini et al., 2006).

Structure of few related chalcones viz., (2E) -1- (2,4-dichlorophenyl) -3-(2-hydrox-3-metoxyphenyl)prop -2-en-1-one (Yathirajan et al., 2007), (2E) -1- (3-hydroxyphenyl) -3-(4-methylphenyl)prop-2-en-1-one (Butcher et al., 2007), (2E)-3-(biphenyl-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (Fischer et al., 2007).

The molecular structure of (I), and the atomic numbering used, is illustrated in Fig. 1. A diagram of the layered crystal packing in the unit cell of (I) is shown in Fig. 2. A substituted chalcone adopts an E configuration with respect to the C=C bond of the enone unit. The molecule is not planar, as can be seen from the dihedral angle of 6.21 (7)° between the two rings. The crystal structure can be described by two types of crossed layers, parallel to (110) and (1–10) respectively (Fig. 2).

The packing is stabilized by Van der Walls interactions and by C—H···π interactions resulting in the formation of three dimensional network (Table 1.).

Experimental

To a mixture of 2,6 dichlorobenzaldehyde (1.75 g, 0.01 mol) and 4-methoxyacetophenone (1.50 g, 0.01 mol) in ethanol 20 ml in the presence of a catalytic amount of sodium hydroxide solution (5 ml) was added slowly with stirring (6 h), the contents of the flask were poured into ice cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and purified by recrystallization in ethanol. Crystal suitable for x-ray analysis was grown by slow evaporation of an acetone solution at room temperature.