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

Yuepiao Cai; Zhankun Wang; Zhe Li; Meiling Zhang; Jianzhang Wu

doi:10.1107/S1600536811017788

. 2011 May 14;67(Pt 6):o1432. doi: 10.1107/S1600536811017788

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

Yuepiao Cai ^a, Zhankun Wang ^b, Zhe Li ^c, Meiling Zhang ^a,^*, Jianzhang Wu ^a

PMCID: PMC3120626 PMID: 21754811

Abstract

In the title compound, C₁₉H₂₀O₅, the dihedral angle between the two aromatic rings is 18.23 (4)°. The crystal structure exhibits only weak C—H⋯π and C—H⋯O contacts between the molecules.

Related literature

For related structures, see: Wu et al. (2011 ▶); Peng et al. (2010 ▶); Huang et al. (2010 ▶); Zhao et al. (2010 ▶). For background and applications of chalcones, see: Wu et al. (2010 ▶, 2011) ▶; Liu et al. (2008 ▶); Zhao et al. (2010 ▶); Nielsen et al. (2005 ▶).

Experimental

Crystal data

C₁₉H₂₀O₅
M _r = 328.35
Orthorhombic,
a = 7.3339 (6) Å
b = 16.8260 (14) Å
c = 26.677 (2) Å
V = 3291.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 133 K
0.35 × 0.33 × 0.31 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.967, T _max = 0.971
22257 measured reflections
3593 independent reflections
3380 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.108
S = 1.02
3593 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536811017788/ff2009sup1.cif

e-67-o1432-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017788/ff2009Isup2.hkl

e-67-o1432-Isup2.hkl^{(176.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811017788/ff2009Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg2ⁱ	0.95	2.89	3.6744 (12)	140
C4—H4⋯Cg1ⁱⁱ	0.95	2.94	3.6921 (12)	137
C17—H17a⋯Cg1ⁱⁱⁱ	0.98	2.96	3.8913 (13)	159
C19—H19a⋯Cg2^iv	0.98	2.82	3.4705 (13)	125
C16—H16c⋯O3^v	0.98	2.51	3.4074 (16)	152
C18—H18a⋯O5^vi	0.98	2.48	3.1578 (16)	126

Open in a new tab

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

Acknowledgments

The authors are grateful for financial support from the Project of Wenzhou Sci. & Tech. Bureau (S20100045), Zhejiang Provincial Natural Science Foundation of China (Y2101108 & Y4090379) and the University Students in Zhejiang science and technology innovation projects (2010R413018).

supplementary crystallographic information

Comment

Chalcones, with the common skeleton of 1,3-diaryl-2-propen-1-one, are essential compounds in flavonoid biosynthesis in plants. They consist of two aromatic rings linked by a three-carbon α,β-unsaturated carbonyl system (Peng et al., 2010; Huang et al., 2010; Zhao et al., 2010.).

Both natural and synthetic chalcones have active biological properties such as antiinflammatory, antitumoral, antioxidant, antibacterial (Wu et al. 2011; Liu et al., 2008; Wu et al. 2010; Zhao, et al. 2010; Nielsen et al. 2005).

In order to investigate activity of chalcones, the title compound has been synthesised. Subsequently, its single-crystal X-ray study was carried out.

The dihedral angle between the two aromatic rings is 18.23 (4)°. There are weak C—H···π and C—H···O intermolecular interactions in the crystal structure. One of the methoxy groups in ortho position of 2,4,6-trimethoxyphenyl ring is slightly bent out of the ring plane [C14-C15-O4-C9 = 16.90 (16)°] while the other methoxy groups are almost coplanar with their parent ring planes [C-C-O-CH₃ = 176.37 (10)°, 176.22 (9)° and -174.09 (10)°].

Experimental

2,4,6-trimethoxybenzaldehyde (2 mmol) and 1-(4-dimethoxyphenyl)ethanone (2 mmol) were dissolved in ehanol (15 ml). The reaction temperature were about 305 K. The reaction was catalyzed by NaOH (20%, 5 drops). The reaction was monitored by thin-layer chromatography. After 10 h, 15 ml H₂O was added and a yellow solid precipitated. The solid was washed with the mixture of water and cold ethanol, and dried. The pure compound was obtained by column chromatography on silica gel (yield: 67%). Single crystals of the compound were grown in a CH₂Cl₂/CH₃CH₂OH mixture (1:1 v/v) at 277 K.