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

Hoong-Kun Fun; Suchada Chantrapromma; P S Patil; S M Dharmaprakash

doi:10.1107/S160053680801413X

. 2008 May 17;64(Pt 6):o1086. doi: 10.1107/S160053680801413X

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

Hoong-Kun Fun ^a,^*, Suchada Chantrapromma ^b,^‡, P S Patil ^c, S M Dharmaprakash ^c

PMCID: PMC2961590 PMID: 21202601

Abstract

In the title chalcone derivative, C₁₅H₉Cl₃O, the dihedral angle between the 2-chlorophenyl and 2,4-dichlorophenyl rings is 41.79 (14)°. Weak C—H⋯O and C—H⋯Cl intramolecular interactions involving the enone unit generate S(5) ring motifs. In the crystal structure, the molecules are arranged in a head-to-tail manner along the a axis. These chains are stacked along the b axis.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see, for example: Fun, Chantrapromma et al. (2007 ▶); Fun, Patil et al. (2007 ▶); Patil, Chantrapromma et al. (2007 ▶; Patil, Fun et al. (2007 ▶). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ▶); Gu et al. (2008 ▶); Patil, Dharmaprakash et al. (2007 ▶).

Experimental

Crystal data

C₁₅H₉Cl₃O
M _r = 311.57
Monoclinic,
a = 50.177 (2) Å
b = 3.8082 (2) Å
c = 13.7297 (7) Å
β = 95.307 (3)°
V = 2612.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 100.0 (1) K
0.39 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.775, T _max = 0.910
13605 measured reflections
2976 independent reflections
2374 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.189
S = 1.13
2976 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.58 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/S160053680801413X/is2291sup1.cif

e-64-o1086-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801413X/is2291Isup2.hkl

e-64-o1086-Isup2.hkl^{(146.2KB, 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—H9A⋯Cl3	0.93	2.66	3.042 (5)	106
C9—H9A⋯O1	0.93	2.53	2.841 (6)	100

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Acknowledgments

This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Nonlinear optical properties of chalcone derivatives have been widely investigated recently (Agrinskaya et al., 1999; Fun, Chantrapromma et al., 2007; Fun, Patil et al., 2007; Patil, Dharmaprakash et al., 2007; Patil, Chantrapromma et al., 2007; Patil, Fun et al., 2007). These molecules show potential in optical-limiting applications due to their large excited-state absorption cross sections (Gu et al., 2008). In view of the importance of chalcones and the continuation of our non-linear optic materials research the title chalcone derivative, (I), was synthesized and its crystal structure is reported here.

In the structure of the title chalcone derivative (Fig. 1), the enone unit O1/C6–C8, the 2-chlorophenyl and 2,4-dichlorophenyl rings are individually planar, with the maximum deviations of 0.016 (6), -0.017 (6) and 0.022 (5) Å for atom C7, C11 and C2, respectively. The molecule is slightly twisted about the C6–C7 bond as indicated by the torsion angles C1–C6–C7–C8 = 132.8 (5)°, C6–C7–C8–C9 = 171.6 (5)°, C7–C8–C9–C10 = -179.7 (5)° and C8–C9–C10–C15 = -160.7 (5)°. The dihedral angles between the 2-chlorophenyl and 2,4-dichlorophenyl rings is 41.79 (14)°. The least-squares plane through the enone unit makes dihedral angles of 10.3 (3)° and 46.9 (2)° with the 2-chlorophenyl and 2,4-dichlorophenyl rings, respectively. The orientation of the prop-2-en-1-one unit can be indicated by the torsion angle O1–C7–C8–C9 = -11.5 (8)°. Bond lengths and angles in (I) are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Fun, Chantrapromma et al., 2007; Fun, Patil et al., 2007; Patil, Dharmaprakash et al., 2007; Patil, Chantrapromma et al., 2007; Patil, Fun et al., 2007).

In the molecular structure, both weak C9—H9A···O1 and C9—H9A···Cl1 intramolecular interactions (Table 1) generate S(5) ring motifs (Bernstein et al., 1995). In the crystal structure (Fig. 2), the molecules are arranged in a head-to-tail manner along the a-axis. These chains are stacked along the b axis.

Experimental

The title compound was synthesized by the condensation of 2-chlorobenzaldehyde (0.01 mol) with 2,4-dichloroacetophenones (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring (4 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 6 h. The resulting crude solid was filtered and dried. Colorless block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from acetone by slow evaporation of the solvent at room temperature.