(1E,4E)-1,5-Bis(2,4,5-trimethoxy­phen­yl)penta-1,4-dien-3-one

Hoong-Kun Fun; Pumsak Ruanwas; Suchada Chantrapromma

doi:10.1107/S1600536809055421

. 2010 Jan 9;66(Pt 2):o307–o308. doi: 10.1107/S1600536809055421

(1E,4E)-1,5-Bis(2,4,5-trimethoxyphenyl)penta-1,4-dien-3-one¹

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

PMCID: PMC2979664 PMID: 21579739

Abstract

There are three molecules in the asymmetric unit of the title compound, C₂₃H₂₆O₇, in which the dihedral angles between two benzene rings are 4.34 (9), 18.11 (8) and 8.54 (8)°. The central penta-1,4-dien-3-one fragment makes dihedral angles of 3.95 (9) and 3.32 (16)° with the two adjacent benzene rings in one molecule, whereas the corresponding pairs of angles in the other two molecules are 10.34 (9)/17.46 (8)° and 7.87 (8)/13.33 (8)°. In the crystal, molecules are linked by intermolecular C—H⋯O and C—H⋯π weak interactions into a three-dimensional network. Finally, π–π interactions [centroid⋯centroid distances = 3.5984 (10) and 3.5545 (10) Å] are observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Harrison et al. (2006 ▶). For background to and applications of chalcones, see: Baeyer & von Villiger (1902 ▶); Gomes et al. (2009 ▶); Gould et al. (1995 ▶); Masuda et al. (1993 ▶); Quincoces et al. (2002 ▶; 2003 ▶; 2008 ▶); Uchida et al. (1998 ▶). For the stability of the temperature controller, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C₂₃H₂₆O₇
M _r = 414.44
Monoclinic,
a = 9.4157 (1) Å
b = 36.8613 (5) Å
c = 19.1226 (3) Å
β = 107.737 (1)°
V = 6321.49 (15) Å³
Z = 12
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.37 × 0.22 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.965, T _max = 0.988
81495 measured reflections
18387 independent reflections
12498 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.150
S = 1.06
18387 reflections
829 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.26 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/S1600536809055421/hb5282sup1.cif

e-66-0o307-sup1.cif^{(47.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055421/hb5282Isup2.hkl

e-66-0o307-Isup2.hkl^{(898.6KB, hkl)}

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

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

Cg3 and Cg4 are the centroids of the C1C–C6C and C12C–C17C rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10B—H10B⋯O1Cⁱ	0.93	2.29	3.149 (2)	153
C10C—H10C⋯O1B	0.93	2.33	3.195 (2)	155
C14B—H14B⋯O1Aⁱⁱ	0.93	2.52	3.353 (2)	149
C21A—H21B⋯O3Aⁱⁱⁱ	0.96	2.49	3.301 (2)	142
C22A—H22C⋯O7C^iv	0.96	2.50	3.435 (2)	165
C22B—H22D⋯O2A^v	0.96	2.50	3.407 (2)	158
C22B—H22F⋯O1Aⁱⁱ	0.96	2.58	3.227 (2)	125
C23A—H23A⋯O5Aⁱ	0.96	2.52	3.308 (2)	140
C23A—H23C⋯O3C	0.96	2.53	3.452 (2)	161
C23C—H23G⋯O5Cⁱ	0.96	2.54	3.305 (2)	136
C18C—H18H⋯Cg4ⁱⁱ	0.96	2.80	3.678 (2)	152
C20A—H20B⋯Cg3^vi	0.96	2.94	3.855 (2)	159

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

Acknowledgments

PR thanks the Graduate School, Prince of Songkla University, for a research grant. The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Bischalcones with the general formula Ar—CH=CH—CO—CH=CH—Ar (Baeyer & Villiger, 1902) are an important class of compounds because they are widely used in many fields such as in organic solid-state photochemistry (Gould et al., 1995), anti-oxidative and anti-inflammatory activities (Masuda et al., 1993), cytotoxicity (Quincoces et al., 2002; 2003; 2008) and activities involving their non-linear optical (Uchida et al., 1998) and fluorescence properties (Gomes et al., 2009). However not much crystal structures of this type of compound were reported. The title bischalcone (I) was synthesized on the account of its fluorescence property which will be reported elsewhere together with the other bichalcone derivatives. We reported herein the crystal structure of (I).

There are three crystallographic independent molecules A, B and C in the asymmetric unit of (I) (Fig. 1) with slight differences in bond angles. The molecular structure of (I), C₂₃H₂₆O₇, is not planar. The dihedral angle between the C1–C6 and C12–C17 benzene rings is 4.34 (9)° in molecule A whereas its is 18.11 (8) and 8.54 (8)° in molecules B and C, respectively. The central penta-1,4-dien-3-one fragment (C7–C11/O1) is planar with the r.m.s. 0.0204 (2) Å for molecule A [0.0227 (2) and 0.0252 (2) Å for molecule B and C, respectively]. This fragment makes the dihedral angles of 3.95 (9) and 3.32 (16)° with the two adjacent C1–C6 and C12–C17 benzene rings, respectively in molecule A whereas the corresponding values are 10.34 (9) and 17.46 (8)° in molecule B; and 7.87 (8) and 13.33 (8)° in the molecule C. The three methoxy groups on C1–C6 benzene ring are essentially planarly attached [C18–O2–C1–C2, C19–O3–C3–C2 and C20–O4–C4–C5 torsion angles of -3.7 (2), 1.4 (3) and -3.9 (2)° in molecule A; -0.2 (3), 3.5 (3) and -1.7 (2)° in molecule B; 3.8 (3), 4.4 (3) and -4.3 (3)° in molecule C]. The middle methoxy group of the 2,4,5-trimethoxyphenyl moeity is co-planar with the C12–C17 benzene ring, with the C22–O6–C15–C14 torsion angle being 1.1 (3)° whereas the other two methoxy groups are twisted with the torsion angles C21–O5–C13–C14 and C23–O7–C16–C17 being -111.48 (18) and -14.4 (3)°, respectively in molecule A [the three corresponding values are -7.6 (3), -30.2 (2) and 9.6 (2)° in molecule B and 0.4 (3), 73.5 (2) and -8.2 (3)° in molecule C]. Intramolecular C—H···O weak interactions (Table 1) generate S(5) ring motifs (Bernstein et al., 1995). The bond distances agree with the literature values (Allen et al., 1987) and are comparable with the related structure (Harrison et al., 2006).

In the crystal packing (Fig. 2), the molecules are linked by intermolecular C—H···O weak interactions (Table 1) into a supramolecular three-dimensional network. The crystal is stabilized by intra- and intermolecular C—H···O weak interactions and C—H···π interactions (Table 1). π–π interactions were observed with the distances of Cg₁···Cg₄ = 3.5984 (10) Å (symmetry code: x, y, z) and Cg₂···Cg₅ = 3.5984 (10) Å (symmetry code: 1 + x, 3/2 - y, 1/2 + z); Cg₁, Cg₂, Cg₃, Cg₄ and Cg₅ are the centroids of C12A–C17A, C1B–C6B, C12B–C17B, C1C–C6C and C12C–C17B rings, respectively.

Experimental

The title compound was synthesized by dissolving 2,4,5-trimethoxybenzaldehyde (0.5 g, 4.85 mmol) in acetone (50 ml). NaOH 50% aqueous solution (2 ml) was then added. After stirring at room temperature for 1 hr, the resulting orange solid was collected by filtration, washed with distilled water and dried. Pale yellow blocks of (I) were recrystalized from acetone/ethanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after a week, Mp. 441–442 K.