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

Jerry P Jasinski; Ray J Butcher; H S Yathirajan; BK Sarojini; V Musthafa Khaleel

doi:10.1107/S160053681100701X

. 2011 Mar 2;67(Pt 4):o756. doi: 10.1107/S160053681100701X

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

Jerry P Jasinski ^a,^*, Ray J Butcher ^b, H S Yathirajan ^c, BK Sarojini ^d, V Musthafa Khaleel ^d

PMCID: PMC3099984 PMID: 21754053

Abstract

In the title compound, C₁₅H₁₁ClO₂, the dihedral angle between the mean planes of the chlorobenzene and hydroxybenzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hydroxyphenyl ring and 11.5 (1)° with the chlorophenyl ring. The crystal packing is stabilized by intermolecular O—H⋯O hydrogen bonds, weak C—H⋯O, C—H⋯π and π–π stacking interactions [centroid–centroid distances = 3.7771 (7) and 3.6917 (7) Å].

Related literature

For the biological properties of chalcones, see: Nowakowska (2007 ▶) and for their role in tubulin polymerization inhibition, see: Edwards et al. (1989 ▶). For related structures, see: Jasinski et al. (2010 ▶, 2011a ▶,b ▶); Butcher et al. (2007a ▶,b ▶); Narayana et al. (2007 ▶); Sarojini et al. (2007a ▶,b ▶). For standard bond lengths, see: Allen et al., (1987 ▶).

Experimental

Crystal data

C₁₅H₁₁ClO₂
M _r = 258.69
Monoclinic,
a = 7.3570 (2) Å
b = 15.6450 (5) Å
c = 10.4954 (3) Å
β = 90.518 (3)°
V = 1207.97 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 200 K
0.51 × 0.45 × 0.36 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.984, T _max = 1.000
10126 measured reflections
4020 independent reflections
2924 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.115
S = 1.07
4020 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 datablocks global, I. DOI: 10.1107/S160053681100701X/sj5108sup1.cif

e-67-0o756-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100701X/sj5108Isup2.hkl

e-67-0o756-Isup2.hkl^{(197.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2ⁱ	0.84	1.83	2.6556 (12)	167
C6—H6A⋯O1ⁱⁱ	0.95	2.57	3.5070 (13)	169
C11—H11A⋯O1ⁱⁱ	0.95	2.55	3.3382 (15)	141
C14—H14A⋯Cg1ⁱⁱⁱ	0.95	2.79	3.7090 (14)	163

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

BKS thanks the P. A. College of Engineering for the research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Chalcones, or 1,3-diaryl-2-propen-1-ones, belong to the flavonoid family. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives. Chalcones have been reported to possess many useful properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Nowakowska, 2007). Certain chalcone derivatives are reported to inhibit the polymerization of tubulin to form microtubules and are therefore antimitotic agents which can be used as antigout agents. The chalcone derivatives are also reported to inhibit the destruction of the myelin sheath in the central nervous system of multiple sclerosis patients and are thus useful in controlling the progressive nature of the disease (Edwards et al., 1989).

In a continuation of our studies on the crystal structures of chalcones (Jasinski et al., 2010, 2011a, 2011b), we report here the synthesis and crystal structure of the title compound, C₁₅H₁₁ClO₂, (I), Fig. 2. The dihedral angle between the mean planes of the chlorobenzene and hydroxybenzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group, the active site in this molecule, makes angles of 18.0 (1)° with the hydroxy benzene and 11.5 (1)° with the chlorobenzene rings, respectively. Bond lengths are normal (Allen et al., 1987) and correspond to those observed in related compounds (Butcher et al., 2007a, 2007b; Narayana et al., 2007; Sarojini et al., 2007a, 2007b). Crystal packing is stabilized by O—H···O hydrogen bonds, weak C—H···O, C—H···Cgπ—ring (Table 1) and π—π intermolecular stacking interactions (Table 2 & Fig. 3).

Experimental

4-Hydroxyacetophenone (1.36 g, 0.01 mol) was mixed with 4-chlorobenzaldeyde (1.40 g, 0.01 mol) and dissolved in ethanol (20 ml) (Fig. 1). To this solution 4 ml of KOH (50%) (10 mL) was added at 0°C. The reaction mixture was stirred for 4 h and poured on to crushed ice. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. The resulting crude yellow solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Crystals suitable for x-ray diffraction studies were grown by the slow evaporation of the solution of the compound in acetone. M.P:419 K. Composition: Found (Calculated) for C₁₅H₁₁ClO₂, C: 69.53 (69.64); H: 4.26 (4.29).