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

Thitipone Suwunwong; Suchada Chantrapromma; Hoong-Kun Fun

doi:10.1107/S1600536808041780

. 2008 Dec 13;65(Pt 1):o120. doi: 10.1107/S1600536808041780

(E)-1-(4-Bromophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one¹

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

PMCID: PMC2968041 PMID: 21581582

Abstract

In the title compound, C₁₈H₁₇BrO₄, the dihedral angle between the 4-bromophenyl and 3,4,5-trimethoxyphenyl rings is 44.18 (6)°. In the crystal structure, the molecules are linked by C—H⋯O and C—H⋯π interactions.

Related literature

For background and applications to chalcones, see: Jung et al. (2008 ▶); Patil et al. (2007 ▶); Patil & Dharmaprakash (2008 ▶); Prasad et al. (2008 ▶); Schlogl & Egger (1963 ▶). For related structures, see: Ng et al. (2006 ▶); Patil et al. (2006 ▶; 2007 ▶). For on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₈H₁₇BrO₄
M _r = 377.22
Tetragonal,
a = 26.6517 (3) Å
c = 4.4238 (1) Å
V = 3142.28 (9) Å³
Z = 8
Mo Kα radiation
μ = 2.63 mm⁻¹
T = 100.0 (1) K
0.55 × 0.12 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.320, T _max = 0.726
142737 measured reflections
9693 independent reflections
6638 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.097
S = 1.07
9693 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.56 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041780/pk2134sup1.cif

e-65-0o120-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041780/pk2134Isup2.hkl

e-65-0o120-Isup2.hkl^{(474.1KB, 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
C11—H11A⋯O1ⁱ	0.93	2.52	3.4391 (16)	170
C17—H17C⋯O3ⁱⁱ	0.96	2.52	3.2789 (16)	136
C16—H16B⋯Cg1ⁱⁱⁱ	0.96	2.97	3.8080 (14)	147

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C10–C15 ring.

Acknowledgments

The authors thank the Thailand Research Fund (TRF) and Prince of Songkla University for financial support and also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Chalcones are compounds in a family of aromatic ketones with two aromatic groups bridged by an enone linkage (Ar-COCH=CH—Ar) (Schlogl & Egger, 1963). They have a wide range of applications covering non-linear optical (NLO) (Patil & Dharmaprakash, 2008) and electro-active fluorescent materials (Jung et al., 2008) to materials with various biological activities. As an example, 1-(4-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)-propenone was found to be able to inhibit growth of some bacteria (Prasad et al., 2008). These interesting properties of chalcones led us to synthesize the title compound so as to study for its antibacterial and cytotoxic activities.

The molecule of the title chalcone derivative (Fig. 1) exists in an E configuration with respect to the C8═C9 double bond [1.3428 (17) Å] with torsion angle C7–C8–C9–C10 = -173.04 (12)°. The whole molecule is not planar as the interplanar angle between 4-bromophenyl and 3,4,5-trimethoxyphenyl rings is 44.18 (6)°. The propenone unit (C7—C9/O1) is nearly planar with the torsion angle O1–C7–C8–C9 = 3.4 (2)°. Atoms O1, C6, C7, C8 and C9 lie on the same plane with the most deviation of -0.018 (1) Å for atom C8. The mean plane through O1/C6/C7/C8/C9 makes interplanar angles of 30.82 (7)° and 13.37 (7)° with the planes of 4-bromophenyl and 3,4,5-trimethoxyphenyl rings, respectively. The three methoxy groups of 3,4,5-trimethoxyphenyl unit have three difference orientations: one methoxy group (at atom C14 position) is co-planar with the attached benzene ring with torsion angle C18–O4–C14–C15 = 0.71 (17)° whereas the one at atom C12 position is twisted with the torsion angle C16–O2–C12–C11 = 10.38 (16)° and one is (+)-syn-clinally attached at atom C13 with the torsion angle C17–O3–C13—C14 = 74.48 (14)°. The bond distances are of normal values (Allen et al., 1987) and are comparable with the closely related structures (Ng et al., 2006; Patil et al., 2006; 2007).

In the crystal packing (Fig. 2), the molecules are linked by weak C11—H11A···O1 intermolcular interactions (Table 1) into cyclic centrosymmetric R²₂(14) dimers (Bernstein et al., 1995). These dimers are stacked along the c axis (Fig. 2) and molecules within the stacks are interlinked by weak C17—H17C···O3 intermolecular interactions. The crystal is stabilized by weak C—H···O interactions (Table 1) and a C—H···π interaction (C16—H16B···Cg₁ = 3.8080 (14) Å), where Cg₁ is the centroid of the C10–C15 ring.

Experimental

The title compound was synthesized by the condensation of 3,4,5-trimethoxybenzaldehyde (0.4 g, 2 mmol) with 4-bromoacetophenone (0.4 g, 2 mmol) in ethanol (50 ml) in the presence of 30% NaOH(aq) (10 ml). After stirring 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. Colorless block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from acetone/methanol (1:1 v/v) by the slow evaporation of the solvent at room temperature over several days, Mp. 403–404 K.