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

Hoong-Kun Fun; Suchada Chantrapromma; Thitipone Suwunwong

doi:10.1107/S1600536811039110

. 2011 Sep 30;67(Pt 10):o2789–o2790. doi: 10.1107/S1600536811039110

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

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

PMCID: PMC3201482 PMID: 22065835

Abstract

The title heteroaryl chalcone derivative, C₁₇H₁₇NO₄, is a condensation product of 2-acetylpyridine and 2,4,6-trimethoxybenzaldehyde. The molecule is roughly planar, the dihedral angle between the pyridine and benzene rings being 5.51 (10)°. All the three methoxy groups are almost co-planar with the bound benzene ring [r.m.s. deviation of 0.0306 (2) Å]. A weak C—H⋯O intramolecular interaction involving one of the ortho-methoxy groups generates an S(6) ring motif. In the crystal, the molecules are linked by weak C—H⋯O interactions into anti-parallel face-to-face pairs. Adjacent pairs are further connected into sheets parallel to the ab plane.

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 ▶); Fun et al. (2010 ▶, 2011 ▶). For background to and applications of chalcones and heteroaryl chalcones, see: Bandgar et al. (2010 ▶); Gacche et al. (2008 ▶); Go et al. (2005 ▶); Isomoto et al. (2005 ▶); Jung et al. (2008 ▶); Suwunwong et al. (2011 ▶); Tewtrakul et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C₁₇H₁₇NO₄
M _r = 299.32
Orthorhombic,
a = 31.563 (2) Å
b = 44.508 (3) Å
c = 3.9504 (3) Å
V = 5549.6 (7) Å³
Z = 16
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.58 × 0.14 × 0.04 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.943, T _max = 0.996
31465 measured reflections
2309 independent reflections
1908 reflections with I > 2σ(I)
R _int = 0.100

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.105
S = 1.09
2309 reflections
267 parameters
1 restraint
All H-atom parameters refined
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.27 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 datablock(s) global, I. DOI: 10.1107/S1600536811039110/rz2642sup1.cif

e-67-o2789-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039110/rz2642Isup2.hkl

e-67-o2789-Isup2.hkl^{(113.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039110/rz2642Isup3.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
C3—H3A⋯O2ⁱ	1.00 (2)	2.45 (3)	3.369 (2)	157.8 (17)
C7—H11B⋯O4	0.97 (3)	2.31 (2)	2.835 (2)	113.1 (18)
C17—H17B⋯O4ⁱⁱ	0.99 (2)	2.46 (2)	3.337 (3)	148 (2)

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

Acknowledgments

The authors thank the Thailand Research Fund (grant No. RSA5280033) and Prince of Songkla University for financial support. They also thank Universiti Sains Malaysia for the Research University 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

Chalcones and heteroaryl chalcones have drawn a lot of interests due to their wide range of biological properties including antioxidant (Gacche et al., 2008), antibacterial (Go et al., 2005; Isomoto et al., 2005), anti-inflammatory and anticancer (Bandgar et al., 2010) as well as HIV-1 protease inhibitory (Tewtrakul et al., 2003) activities. Furthermore they also exhibit fluorescent property (Jung et al., 2008; Suwunwong et al., 2011). In our on-going research on the biological and fluorescent properties of chalcones and heteroaryl chalcones (Chantrapromma et al., 2009; Fun et al., 2010, 2011; Suwunwong et al., 2011), the title heteroaryl chalcone derivative (I) was synthesized in order to study the effects of substituted postions on the fluorescent property in comparision with the closely related compounds (Fun et al., 2011; Suwunwong et al., 2011). In addition (I) was also tested for analgesic and antibacterial activities. Our results showed that (I) exhibits a moderate analgesic activity but is inactive for antibacterial activity. Herein we report the crystal structure of (I).

The molecule of the title heteroaryl chalcone derivative (Fig. 1) exists in an E configuration with respect to the C7═C8 double bond [1.341 (3) Å]. The torsion angle C6–C7–C8–C9 is 179.0 (2)°. The molecule is almost planar with a dihedral angle between the pyridine and 2,4,6-trimethoxyphenyl rings of 5.51 (10)°. Atoms of the propenone bridge (C6, C7, C8 and O1) lie on the same plane [r.m.s. deviation of 0.017 (2)] and the torsion angle O1–C6–C7–C8 is -5.8 (4)°. The mean plane through this bridge makes dihedral angles of 6.96 (16) and 11.72 (16)° with the planes of pyridine and benzene rings, respectively. All the three substituted methoxy groups of the 2,4,6-trimethoxyphenyl unit are co-planar with the phenyl ring as indicated by the torsion angles C15–O2–C10–C11 = -0.4 (3)°, C16–O3–C12–C13 = 0.9 (3)° and C17–O4–C14–C13 = -4.7 (3)°. In the molecule, a weak intramolecular C7—H7A···O4 interaction (Table 1) generates an S(6) ring motif (Bernstein et al., 1995). The bond distances are of normal values (Allen et al., 1987) and comparable with related structures (Chantrapromma et al., 2009; Fun et al., 2010; 2011).

In the crystal packing (Fig. 2), only the two ortho-methoxy groups are involved in weak C—H···O interactions (Table 1). The adjacent molecules are linked by weak C17—H17B···O4 interaction (Table 1) into anti-parallel face-to-face pairs. The adjacent pairs were further connected by weak C3—H3A···O2 interactions (Table 1) into sheets parallel to the ab plane which are stacked down the c axis. The crystal may be further stabilized by C···O [3.203 (2) Å] short contacts.

Experimental

The title compound was synthesized by the condensation reaction of 2,4,6-trimethoxybenzaldehyde (0.40 g, 2 mmol) with 2-acetylpyridine (0.20 g, 2 mmol) in ethanol (30 ml) in the presence of 30% NaOH(aq) (5 ml). After stirring in ice bath at 278 K for 4 h, the resulting pale yellow solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Pale yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from acetone/ethanol (1:1 v/v) by the evaporation of the solvent at room temperature after several days, M.p. 392-393 K.