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

Hoong-Kun Fun; Thawanrat Kobkeatthawin; Pumsak Ruanwas; Suchada Chantrapromma

doi:10.1107/S1600536810026346

. 2010 Jul 10;66(Pt 8):o1973–o1974. doi: 10.1107/S1600536810026346

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

Hoong-Kun Fun ^a,^*,^‡, Thawanrat Kobkeatthawin ^b, Pumsak Ruanwas ^b, Suchada Chantrapromma ^b,^§

PMCID: PMC3007376 PMID: 21588292

Abstract

Molecules of the title aminochalcone, C₁₈H₁₉NO₄, are twisted, with a dihedral angle of 11.26 (6)° between the 4-aminophenyl and 2,4,5-trimethoxyphenyl rings. The conformations of the three methoxy groups with respect to the benzene ring are slightly different. Two methoxy groups are almost coplanar with the attached benzene ring [C—O—C—C torsion angles of −1.45 (19) and 1.5 (2)°], while the third is (−)-synclinal with the attached benzene ring [C—O—C—C = −81.36 (17)°]. In the crystal structure, molecules are stacked into columns along the b axis and molecules in adjacent columns are linked by N—H⋯O hydrogen bonds into V-shaped double columns. Weak π–π interactions are also observed, with a centroid-centroid distance of 3.7532 (8) Å.

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 ▶, 2010 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Batovska et al. (2007 ▶); Jung et al. (2008 ▶); Kim et al. (2010 ▶); Nielsen et al. (2004 ▶); Niu et al. (2006 ▶); Romagnoli et al. (2008 ▶); Tewtrakul et al. (2003 ▶); Won et al. (2005 ▶); Xia et al. (2000 ▶).

Experimental

Crystal data

C₁₈H₁₉NO₄
M _r = 313.34
Monoclinic,
a = 13.6117 (2) Å
b = 10.3540 (2) Å
c = 22.3920 (4) Å
β = 100.879 (1)°
V = 3099.11 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.38 × 0.32 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.965, T _max = 0.991
19818 measured reflections
4506 independent reflections
3581 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.131
S = 1.05
4506 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.23 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/S1600536810026346/fj2326sup1.cif

e-66-o1973-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026346/fj2326Isup2.hkl

e-66-o1973-Isup2.hkl^{(220.9KB, 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
N1—H1N1⋯O1ⁱ	0.86 (2)	2.12 (2)	2.9692 (16)	170.4 (17)
N1—H2N1⋯O1ⁱⁱ	0.88 (2)	2.21 (2)	3.0176 (17)	153.4 (19)

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

Acknowledgments

The authors thank the Thailand Research Fund (TRF) for the research grant (RSA5280033), Prince of Songkla University and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. TK and PR thank the Graduate School, Prince of Songkla University, for partial financial support.

supplementary crystallographic information

Comment

Chalcones are important compounds which have considerable interesting applications involving biological activities such as antibacterial (Nielsen et al., 2004), antifungal (Batovska et al., 2007), anti-inflammatory (Won et al., 2005), anti-HIV-1 protease inhibition (Tewtrakul et al., 2003) and antitumor (Romagnoli et al., 2008) properties. Moreover they also show electroactive fluorescent properties (Jung et al., 2008; Niu et al., 2006). From previous reports, aminochalcone showed good cytotoxicity in vitro against human tumor cell lines (Xia et al., 2000) and was a new class of both activator and inhibitor of the TREK2 channel which turn out to be an important channel in charge of tuning neuronal transmitter and hormone levels (Kim et al., 2010). In continuing our on-going research on bioactivity and fluorescence properties of chalcones (Chantrapromma et al., 2009; 2010; Suwunwong et al., 2009), the title aminochalcone (I) was synthesized. (I) doesn't possess antibacterial and cytotoxic activities. However (I) exhibits fluorescence with the maximum emission at 480 nm when the compound is excited at 320 nm in chloroform solution.

The molecule of the title aminochalcone, (Fig. 1), exists in an E configuration with respect to the C8═C9 double bond [1.3407 (19) Å] with torsion angle C7–C8–C9–C10 = 177.99 (13)°. The whole molecule is not planar indicated by the dihedral angle between 4-aminophenyl and 2,4,5-trimethoxyphenyl rings being 11.26 (6)°. The propenone unit (C7—C9/O1) is planar with the r.m.s. deviation 0.0031 (1) Å. The mean plane through the propenone unit makes dihedral angles of 11.70 (9) and 9.19 (9)° respectively with the planes of 4-aminophenyl and 2,4,5-trimethoxyphenyl rings. The three methoxy groups of 2,4,5-trimethoxyphenyl unit have two different orientations: two methoxy groups (at atom C11 and C13 positions) are co-planar with the attached benzene ring with torsion angles C16–O2–C11–C12 = -1.45 (19)° and C17–O3–C13–C12 = 1.5 (2)° whereas the one at atom C14 position is (-)-syn-clinally attached with the torsion angle C18–O4–C14–C13 = -81.36 (17)°. Weak C9—H9A···O1 and C9—H9A···O2 intramolecular interactions generate two S(5) motifs (Bernstein et al., 1995) (Fig. 1 and Table 1). The bond distances and angles are of normal values (Allen et al., 1987) and are comparable with the related structures (Chantrapromma et al., 2009; 2010; Suwunwong et al., 2009).

In the crystal packing (Fig. 2), the molecules are stacked into columns along the b axis. The molecules in the adjacent columns are linked by N—H···O hydrogen bonds (Table 1) into a V-shape double columns. π–π interaction was observed with the Cg₁···Cg₂ distance of 3.7532 (8) Å (symmetry code -1/2 - x, 3/2 - y, 1 - z); Cg₁ and Cg₂ are the centroids of C1–C6 and C10–C15 rings, respectively.

Experimental

The title compound was synthesized by the condensation of 2,4,5-trimethoxybenzaldehyde (0.40 g, 2 mmol) with 4-aminoacetophenone (0.28 g, 2 mmol) in ethanol (30 ml) in the presence of 30% NaOH(aq) (5 ml). After stirring for 3 h at room temperature, the resulting orange solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Orange block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystallized from acetone by the slow evaporation of the solvent at room temperature after several days, Mp. 393–394 K.