(E)-1-(4-Meth­oxy­phen­yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

P S Carvalho-Jr; L O Sallum; A F Cidade; G L B Aquino; H B Napolitano

doi:10.1107/S1600536811028984

. 2011 Jul 23;67(Pt 8):o2126. doi: 10.1107/S1600536811028984

(E)-1-(4-Methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

P S Carvalho-Jr ^a,^*, L O Sallum ^a, A F Cidade ^a, G L B Aquino ^a, H B Napolitano ^a

PMCID: PMC3213567 PMID: 22091144

Abstract

The title compound, C₁₉H₂₀O₅, was synthesized by reaction of 4-methoxyacetophenone and 3,4,5-trimethoxy-benzaldehyde. The aromatic rings form a dihedral angle of 36.39 (7)°. Two intramolecular C—H⋯O hydrogen bonds occur. The crystal packing features weak C—H⋯O interactions.

Related literature

For background to chalcones and the biological activity and derivatives, see: Dhar (1981 ▶); Dimmock et al. (1999 ▶). For their applications as organic non-linear optical materials, see: Sarojini et al. (2006 ▶) and for their choleretic and hepatoprotective activity, see: Ni et al. (2004 ▶). For the synthesis of chalcones, see: Patil et al. (2009 ▶). For the potential use of these compounds or chalcone-rich plant extracts as drugs or food preservatives, see: Di Carlo et al. (1999 ▶). For related structures, see: Sathiya Moorthi et al. (2005 ▶); Cai et al. (2011 ▶); Vijay Kumar et al. (2011 ▶); Bibila Mayaya Bisseyou et al. (2007 ▶). The title compound wss prepared by an aldol Claisen–Schmidt condensation reaction, see: Bandgar et al. (2009 ▶, 2010 ▶); Hathaway (1987 ▶).

Experimental

Crystal data

C₁₉H₂₀O₅
M _r = 328.35
Monoclinic,
a = 7.5770 (1) Å
b = 16.2530 (3) Å
c = 14.0850 (3) Å
β = 107.528 (1)°
V = 1654.02 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.2 × 0.1 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer
27371 measured reflections
3733 independent reflections
2907 reflections with I > 2σ(I)
R _int = 0.130

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.174
S = 1.02
3733 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028984/zj2014sup1.cif

e-67-o2126-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028984/zj2014Isup2.hkl

e-67-o2126-Isup2.hkl^{(179.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811028984/zj2014Isup3.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
C9—H9⋯O2	0.93	2.51	3.415 (2)	165
C16—H16A⋯O2	0.96	2.55	3.484 (2)	165
C18—H18C⋯O1ⁱ	0.96	2.53	3.332 (2)	142

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Brazilian Federal Agency CAPES.

supplementary crystallographic information

Comment

Chalcones are a medicinally important class of compounds and are known for possessing various biological activities such as antibacterial, antiviral, anthelmintic, amoebicidal, antiulcer, insecticidal, antiprotozoal, anticancer, cytotoxic, immunosuppressive activities and other bioactivities (Dhar, 1981; Dimmock et al., 1999). Recently, some chalcones were approved for therapeutical use, such as methoxychalcone (E)-3-(4-methoxyphenyl)-1-(2,4-methoxyphenyl)prop-2-en-1-one, marketed in France and Italy, with choleretic and hepatoprotective activities (Ni et al., 2004). Moreover, a literature survey showed dimethoxy and trimethoxychalcone derivatives as effective anti-inflammatory agents (Bandgar et al., 2010).

The (E)-3-(3,4,5-trimethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one is a methoxychalcone which the structure shows two aromatic rings linked by prop-2-en-1-one group. The refined molecular structure is shown in Fig. 1. Due to p-π conjugation, the C_sp²—O bonds [O2—C7 = 1.2249 (2) Å] are significantly shorter than the C_sp³—O bonds [O1—C19 = 1.4240 (2) Å; O3—C18 = 1.415 (2) Å; O4—C17 = 1.413 (2) Å and O5—C16 = 1.4294 (2) Å]. The methoxy substituted groups around the benzene rings are almost planar and the dihedral angles C5—C6—C7—C8, C6—C7—C8—C9, C7—C8—C9—C10 and C8—C9—C10—C11 are -23.0 (2)°, 169.3 (2)°, 177.7 (2)° and -4.4 (2)°, respectively, indicating the molecule has a non-planar conformation.

The crystal structure is stabilized by C—H···O contacts (Table 1). There is intermolecular hydrogen bonding involving C9 acting as H-bond donor, via H9, to O2 in the adjacent molecules at -x+1, -y+1, -z resulting in a dimer.

Experimental

The title compound, C₁₉H₂₀O₅, has been prepared by the aldol Claisen-Schmidt condensation (Hathaway, 1987; Bandgar et al., 2009) by the reaction of a mixture of 4-methoxy-acetophenone (0,3 mg; 2 mmol) and 3,4,5-trimethoxy-benzaldehyde (0,39 mg; 2 mmol) and NaOH (50% p/v) at 257 K for 24 h. The light yellow solid (m.p. 404.25 - 405.65 K) thus obtained was filtered, washed with water and dried. Crystals of suitable quality for single crystal X-ray diffraction were grown in methanol.