1-(2,4-Dichloro­phen­yl)-3-(4-methyl­phen­yl)prop-2-en-1-one

Hoong-Kun Fun; Samuel Robinson Jebas; P S Patil; S M Dharmaprakash

doi:10.1107/S1600536808011008

. 2008 Apr 30;64(Pt 5):o936. doi: 10.1107/S1600536808011008

1-(2,4-Dichlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*, Samuel Robinson Jebas ^a,^‡, P S Patil ^b, S M Dharmaprakash ^b

PMCID: PMC2961235 PMID: 21202417

Abstract

The molecule of the title compound, C₁₆H₁₂Cl₂O, adopts an E configuration. The dihedral angle between the two benzene rings is 42.09 (5)°. In the crystal structure, molecules are linked into a three-dimensional framework by weak C—H⋯O interactions and by C—H⋯π interactions involving the methylphenyl ring.

Related literature

For related literature, see: Agrinskaya et al. (1999 ▶); Gu et al. (2008 ▶); Patil et al. (2006 ▶); Patil, Dharmaprakash et al. (2007 ▶); Patil, Teh et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₂Cl₂O
M _r = 291.16
Orthorhombic,
a = 12.54850 (1) Å
b = 7.47750 (1) Å
c = 28.7764 (3) Å
V = 2700.13 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 100.0 (1) K
0.47 × 0.39 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.811, T _max = 0.914
50054 measured reflections
7296 independent reflections
4995 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.148
S = 1.07
7296 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011008/ci2584sup1.cif

e-64-0o936-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011008/ci2584Isup2.hkl

e-64-0o936-Isup2.hkl^{(349.9KB, 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
C2—H2⋯O1ⁱ	0.93	2.55	3.4352 (15)	159
C8—H8⋯O1ⁱⁱ	0.93	2.55	3.1995 (14)	127
C11—H11⋯Cg1ⁱⁱⁱ	0.93	2.81	3.5611 (13)	139
C14—H14⋯Cg1^iv	0.93	2.93	3.7066 (13)	142

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C10–C15 benzene ring.

Acknowledgments

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for the award of a post-doctoral research fellowship. PSP thanks the DRDO, Government of India, for a Senior Research Fellowship (SRF). This work is also supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006.

supplementary crystallographic information

Comment

Chalcone derivatives have been studied extensively owing to their fascinating, technologically relevant nonlinear optical properties (Gu et al., 2008; Agrinskaya et al., 1999; Patil et al., 2006; Patil, Dharmaprakash et al., 2007; Patil, Teh et al., 2007).

The title molecule exhibits an E configuration with respect to the C8═C9 double bond [1.3424 (14) Å]; the C7—C8—-C9—-C10 torsion angle is 179.61 (11)°. The dihedral angle between the two benzene rings is 42.09 (5)°. The bond lengths and angles in the title molecule have normal values.

The crystal structure is stabilized by weak C—H···O intermolecular hydrogen bonding interactions (Table 1), which link the molecules into a three-dimensional framework (Fig. 2). In addition weak C—H..π interactions involving the C10—C15 benzene ring (centroid Cg1) is observed.

Experimental

The title compound was synthesized by the condensation of p-tolualdehyde (0.01 mol) with 2,4-dichloroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 2 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 collected by filtration and dried. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of an acetone solution at room temperature.