(E)-3-(3,5-Dimeth­oxy­phen­yl)-1-(1-hy­droxy­naphthalen-2-yl)prop-2-en-1-one

Ha-Jin Lee; Yoongho Lim; Dongsoo Koh

doi:10.1107/S1600536812046715

. 2012 Nov 24;68(Pt 12):o3403. doi: 10.1107/S1600536812046715

(E)-3-(3,5-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one

Ha-Jin Lee ^a, Yoongho Lim ^b, Dongsoo Koh ^c,^*

PMCID: PMC3588993 PMID: 23476229

Abstract

In the title molecule, C₂₁H₁₈O₄, the C=C bond of the central enone group adopts a trans conformation. The dihedral angle formed by the naphthalene ring system and the benzene ring is 2.97 (11)°. The hydroxy group is involved in an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into chains along [001].

Related literature

For the synthesis and biological properties of chalcone derivatives, see: Sharma et al. (2012 ▶); Singh et al. (2012 ▶); Bandgar et al. (2010 ▶); Hans et al. (2010 ▶); Hwang et al. (2011 ▶). For related structures, see: Fadzillah et al. (2012 ▶); Jasinski et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₁H₁₈O₄
M _r = 334.35
Orthorhombic,
a = 30.179 (3) Å
b = 3.9127 (3) Å
c = 13.7363 (12) Å
V = 1622.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.24 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
11095 measured reflections
3479 independent reflections
1828 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.102
S = 0.94
3479 reflections
229 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Click here for additional data file.^{(19.4KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046715/lh5555sup1.cif

e-68-o3403-sup1.cif^{(19.4KB, cif)}

Click here for additional data file.^{(170.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046715/lh5555Isup2.hkl

e-68-o3403-Isup2.hkl^{(170.6KB, hkl)}

Click here for additional data file.^{(6.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812046715/lh5555Isup3.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
O4—H4⋯O1	0.84	1.75	2.503 (3)	147
C7—H7C⋯O1ⁱ	0.98	2.59	3.157 (4)	117
C10—H10B⋯O2ⁱ	0.98	2.54	3.344 (4)	139

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Chalcones are one of the secondary metabolites in plants and belong to a flavonoid class with a C6—C3—C6 skeleton and C3 skeleton which is an α,β-unsaturated carbonyl (enone) group. Because of their diverse biological activities including anticancer (Singh et al., 2012), anti-inflammatory (Bandgar et al., 2010), anti-tubercular (Hans et al., 2010), and antimicrobial (Sharma et al., 2012), various chlacones have been isolated from natural sources and syntheized. In continuation of our research to develop novel chalcone derivatives which show broad range of biological activities (Hwang et al., 2011) the title compound was synthesized and and its crystal structure was determined.

The molecular structure of the title compound is shown in Fig .1. The C2═C3 bond of the central enone group adopts a trans configuration. The dihedral angle formed by the naphthalene ring system and the benzene ring is 2.97 (11)°. The C1═O1 bond [1.242 (3) Å] is slightly longer than the standard value (Allen et al. 1987) as this group is involved in an intramolecular O—H···O hydrogen bond with the hydroxy group. In the crystal, weak C—H···O hydrogen bonds link the molecules into one-dimensional chains along [001] (Fig. 2). Examples of structures of substituted prop-2-en-1-one compounds have been published (Fadzillah et al., 2012; Jasinski et al., 2011).

Experimental

A solution of 1-hydroxy-2-acetonaphthone (186 mg, 1 mmol) and 3,5-dimethoxybenzaldehyde (166 mg, 1 mmol) was dissolved in 10 ml of ethanol and the temperature was adjusted to around 276-277K in an ice-bath. To the cooled reaction mixture was added 0.5 ml of 50% aqueous KOH solution, and the reaction mixture was stirred at room temperature for 24 h. This mixture was poured into iced water (20 ml) was acidified with 6 N HCl solution. The mixture was extracted with ethylacetate (3 × 20 ml) and the combined organic layers were dried under MgSO₄. Filtration and evaporation of the filtrate gave a residue which was purified by flash chromatography to give the title compound (210 mg, 63%). Recrystallization of the title compound in ethanol gave orange colored crystals (mp: 422-424K).