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

Jerry P Jasinski; James A Golen; Prakash S Nayak; B Narayana; H S Yathirajan

doi:10.1107/S1600536812000505

. 2012 Jan 11;68(Pt 2):o366. doi: 10.1107/S1600536812000505

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

Jerry P Jasinski ^a,^*, James A Golen ^a, Prakash S Nayak ^b, B Narayana ^b, H S Yathirajan ^c

PMCID: PMC3275046 PMID: 22346991

Abstract

In the title compound, C₁₅H₁₀Cl₂O₂, the dihedral angle between the mean planes of the two benzene rings is 7.7 (6)°. The crystal packing is influenced by O—H⋯O hydrogen bonds, which form chains along [010]. Weak π–π stacking interactions [centroid–centroid distance = 3.6697 (13) Å] are observed, which may contribute to the crystal packing stability.

Related literature

For the pharmacological activity of chalcones, see: Bandgar et al. (2010 ▶); Cheng et al. (2008 ▶); Dhar (1981 ▶); Dimmock et al. (1999 ▶); Nowakowska (2007 ▶). For the synthesis of chalcone derivatives, see: Samshuddin et al. (2010 ▶; 2011 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011 ▶). For related structures, see: Fun et al. (2011 ▶); Jasinski et al. (2011 ▶).

Experimental

Crystal data

C₁₅H₁₀Cl₂O₂
M _r = 293.13
Triclinic,
a = 7.2551 (6) Å
b = 7.8351 (7) Å
c = 12.8049 (11) Å
α = 92.367 (7)°
β = 102.946 (8)°
γ = 109.011 (8)°
V = 665.51 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 173 K
0.34 × 0.15 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.854, T _max = 0.972
5430 measured reflections
3174 independent reflections
2417 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.115
S = 1.01
3174 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000505/vm2148sup1.cif

e-68-0o366-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000505/vm2148Isup2.hkl

e-68-0o366-Isup2.hkl^{(155.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812000505/vm2148Isup3.cml

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
O2—H2O⋯O1ⁱ	0.84 (2)	1.88 (2)	2.7168 (17)	176 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

PSN thanks Mangalore University for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Chalcones are abundant in edible plants and considered as the precursors of flavonoids and isoflavonoids. They have also been shown to display a diverse array of pharmacological activities (Dhar, 1981; Nowakowska, 2007) including anti-infective, anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor, anticancer and mutagenic properties (Dimmock et al., 1999; Cheng et al., 2008; Bandgar et al., 2010). The basic skeleton of chalcones which possess an α,β-unsaturated carbonyl group is a useful synthone for the synthesis of various biodynamic cyclic derivatives such as pyrazoline, isoxazoline, 2,4,6-triaryl pyridine, benzodiazepine and cyclohexenone derivatives (Samshuddin et al., 2010; 2011; Fun et al., 2010; Jasinski et al., 2010; Baktır et al., 2011). The crystal structures of some chalcones, viz., (2E)-3-[3-(benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one (Fun et al., 2011), (2E)-3-(4-chlorophenyl)-1-(4-hydroxyphenyl) prop-2-en-1-one (Jasinski et al., 2011), have been reported. In continuation of our studies on chalcones and their derivatives, the title compound (I) was prepared and its crystal structure is reported.

In the title compound, C₁₅H₁₀Cl₂O₂, the dihedral angle between the mean planes of the two benzene rings is 7.7 (6)° (Fig. 1). O—H···O hydrogen bonds (Table 1) are observed between the hydroxyl hydrogen and propene oxygen atoms forming 1-D polymeric chains along [010]. In addition, weak π–π stacking interactions (Cg1···Cg2 distance of 3.6697 (13) Å; Cg1 and Cg2 are the centroids of the C1–C5 ring and C10–C15 ring, respectively) are observed which may contribute to crystal packing stability.

Experimental

To a mixture of 2-hydroxybenzaldehyde (1.22 g, 0.01 mol) and 3,4-dichloroacetophenone (1.89 g, 0.01 mol) in ethanol (40 ml), 10 ml of 10% sodium hydroxide solution was added and stirred at 278–288 K for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from DMF by the slow evaporation method. The yield of the compound was 86%. (M.P.: 392 K).