(E)-1-(4-Chloro­phen­yl)-3-(4-methyl­phen­yl)prop-2-en-1-one

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

doi:10.1107/S160053680801324X

. 2008 May 10;64(Pt 6):o1038. doi: 10.1107/S160053680801324X

(E)-1-(4-Chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one

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

PMCID: PMC2961484 PMID: 21202560

Abstract

The title compound, C₁₆H₁₃ClO, adopts an E configuration with respect to the C=C double bond of the propenone unit. The dihedral angle between the two benzene rings is 45.9 (2)°. In the crystal structure, molecules are arranged into sheets parallel to the ac plane and the sheets are stacked along the b axis. This arrangement is stabilized by weak intermolecular C—H⋯π interactions involving both aromatic rings.

Related literature

For applications of chalcones in non-linear optics, see: Agrinskaya et al. (1999 ▶). For related structures, see: Patil, Dharmaprakash et al. (2007 ▶); Patil, Fun et al. (2007 ▶); Patil, Rosli et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₃ClO
M _r = 256.71
Monoclinic,
a = 15.2632 (3) Å
b = 14.0146 (3) Å
c = 5.8487 (1) Å
β = 92.154 (1)°
V = 1250.20 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100.0 (1) K
0.34 × 0.18 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.908, T _max = 0.986
15494 measured reflections
3661 independent reflections
2534 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.129
S = 1.04
3661 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.27 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/S160053680801324X/ci2595sup1.cif

e-64-o1038-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801324X/ci2595Isup2.hkl

e-64-o1038-Isup2.hkl^{(175.9KB, 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
C9—H9⋯O1	0.93	2.50	2.820 (2)	100
C5—H5⋯Cg1ⁱ	0.93	2.98	3.525	119
C2—H2⋯Cg2ⁱⁱ	0.93	2.93	3.563	127
C14—H14⋯Cg2ⁱⁱⁱ	0.93	2.80	3.495	132

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

Acknowledgments

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

supplementary crystallographic information

Comment

Recently, significant progress has been achieved in the growth of noncentrosymmetric crystals for second harmonic generation (SHG), mostly that of chalcone derivatives substituted with different donor/acceptor substituents (Agrinskaya et al., 1999; Patil, Dharmaprakash et al., 2007; Patil, Fun et al., 2007; Patil, Rosli et al., 2007). Herein we report the crystal structure of the title compound.

The title molecule (Fig.1) exhibits an E configuration with respect to the C8?C9 double bond, with the C7—C8—C9—C10 torsion angle being -175.3 (2)°. The bond lengths and angles are comparable to those observed in related structures (Patil, Dharmaprakash et al., 2007; Patil, Fun et al., 2007; Patil, Rosli et al., 2007). The dihedral angle between the two benzene rings is 45.9 (1)°.

In the molecular structure, an intramolecular C—H···O hydrogen bond generates an S(5) ring motif. In the crystal structure, the molecules are arranged into sheets parallel to the ac plane and the sheets are stacked along the b axis (Fig. 2). This arrangement is stabilized by weak intermolecular C—H···π interactions involving both aromatic rings, Table 1.

Experimental

The title compound was synthesized by the condensation of p-tolualdehyde (0.01 mol) with 4-chloroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 6 h, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 12 h. The resulting crude solid was filtered and dried. Single crystals suitable for X-ray diffraction were grown by slow evaporation of an acetone solution at room temperature.