(E)-1-(2-Fur­yl)-3-(2,4,6-trimeth­oxy­phen­yl)prop-2-en-1-one

Hoong-Kun Fun; Thitipone Suwunwong; Suchada Chantrapromma; Chatchanok Karalai

doi:10.1107/S1600536810035762

. 2010 Sep 15;66(Pt 10):o2559–o2560. doi: 10.1107/S1600536810035762

(E)-1-(2-Furyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Thitipone Suwunwong ^b, Suchada Chantrapromma ^b,^§, Chatchanok Karalai ^b

PMCID: PMC2983191 PMID: 21587546

Abstract

In the title heteroaryl chalcone derivative, C₁₆H₁₆O₅, the dihedral angle between the furan and benzene rings is 14.45 (6)°. The three methoxy groups are almost coplanar with their attached benzene ring [C—C—O—C torsion angles = 2.07 (17), −5.04 (17) and 2.85 (16)°]. An intramolecular C—H⋯O hydrogen bond occurs. In the crystal, adjacent molecules are linked into X-shaped chains along the c axis by weak C—H⋯O(enone) interactions. These chains are stacked along the b axis. C⋯O [3.3308 (13)–3.4123 (14) Å] short contacts are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2009 ▶); Suwunwong et al. (2009 ▶. For background to and applications of chalcones and heteroaryl chalcones, see: Gaber et al. (2008 ▶); Go et al. (2005 ▶); Jung et al. (2008 ▶); Ng et al. (2009 ▶); Ni et al. (2004 ▶); Nowakowska (2007 ▶); Patil & Dharmaprakash (2008 ▶) and Tewtrakul et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C₁₆H₁₆O₅
M _r = 288.29
Monoclinic,
a = 38.5688 (5) Å
b = 3.93493 (5) Å
c = 18.2638 (3) Å
β = 103.901 (1)°
V = 2690.68 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.41 × 0.15 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.957, T _max = 0.990
20657 measured reflections
3941 independent reflections
3077 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.113
S = 1.06
3941 reflections
254 parameters
All H-atom parameters refined
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035762/hb5630sup1.cif

e-66-o2559-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035762/hb5630Isup2.hkl

e-66-o2559-Isup2.hkl^{(193.3KB, 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
C1—H1⋯O2ⁱ	0.956 (15)	2.496 (15)	3.3512 (14)	148.9 (13)
C6—H6⋯O5	0.965 (15)	2.260 (14)	2.8197 (15)	116.0 (11)
C14—H14A⋯O4ⁱⁱ	0.975 (15)	2.589 (16)	3.4462 (14)	146.7 (11)
C15—H15A⋯O1ⁱⁱⁱ	0.989 (16)	2.546 (16)	3.4293 (18)	148.6 (12)
C16—H16A⋯O1ⁱⁱⁱ	0.982 (16)	2.575 (16)	3.4120 (16)	143.0 (12)

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

Acknowledgments

The authors thank the Thailand Research Fund (TRF) for a research grant (RSA 5280033) and the Prince of Songkla University for financial support. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811160. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is acknowledged for the bacterial assay.

supplementary crystallographic information

Comment

Chalcone and heteroaryl chalcones are very interesting due to their variety of applications with biological activities. Many of them possess analgesic, anti-inflammatory and antibacterial properties (Go et al., 2005; Ni et al., 2004; Nowakowska, 2007) as well as HIV-1 protease inhibitory (Tewtrakul et al., 2003) and tyrosinase inhibitory (Ng et al., 2009) activities. Moreover synthetic chalcones and heteroaryl chalcones have also been found to exhibit non-linear optical (Patil & Dharmaprakash, 2008), fluorescent (Jung et al., 2008) and laser properties (Gaber et al., 2008) . In continuing our on-going research on antibacterial activities and fluorescence properties of chalcones and heteroaryl chalcone derivatives, the title heteroaryl chalcone was synthesized in order to study its antibacterial and fluorescence properties. However our results show that (I) do not possess fluorescence property. In addition our biological testing found that (I) was inactive against the tested bacteria strains which are Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecalis, Pseudomonas aeruginosa, Salmonella typhi and Shigella sonnei. Herein we report the crystal structure of (I).

The molecule of the title heteroaryl chalcone (Fig. 1) exists in an E configuration with respect to the C6═C7 double bond [1.3512 (16) Å] with the C5–C6–C7–C8 torsion angle being -176.44 (12)°. The whole molecule is slightly twisted with the dihedral angle between the furan and benzene rings being 14.45 (6)°. Atoms of the propenone unit (C5, C6, C7 and O1) lie on the same plane [r.m.s. 0.0179 (1)]. This plane makes dihedral angles of 11.38 (8) and 9.12 (8)° with furan and phenyl rings, respectively. All the three substituted methoxy groups of 2,4,6-trimethoxyphenyl unit are almost co-planar with the phenyl ring as indicated by torsion angles C14–O3–C9–C10 = 2.07 (17)°, C15–O4–C11–C12 = -5.04 (17)° and C16–O5–C13–C12 = 2.85 (16)°. In the structure, a weak intramolecular C6—H6···O5 interaction generates an S(6) ring motif (Bernstein et al., 1995) (Table 1). The bond lengths have normal values (Allen et al., 1987) and bond lengths and angles are comparable with its related structures (Chantrapromma et al., 2009; Suwunwong et al., 2009).

In the crystal packing, all the three methoxy groups involve in weak intermolecular C—H···O interactions (Table 1). The adjacent molecules are linked into X-shape chains along the c axis through the enone unit by weak C—H···O interactions (Fig. 2, Table 1). The adjacent chains are arranged into face-to-face manner (Fig. 3) and stacked along the b axis (Fig. 3). The crystal is further stabilized by C···O[3.3308 (13)-3.4123 (14) Å] short contacts.

Experimental

The title compound was prepared by the condensation of the solution of 2-furyl methylketone (2 mmol, 0.22 g) in ethanol (15 ml) and 2,4,6-trimethoxybenzaldehyde (2 mmol, 0.40 g) in ethanol (15 ml) in the presence of 20% NaOH (aq) 5 ml at 278 K for 5 hr. The resulting solid which was obtained was further collected by filtration, washed with distilled water and dried in air. Colorless blocks of (I) were recrystalized from acetone/ethanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after several days, Mp. 390–391 K.