(E)-3-[4-(Dimethyl­amino)phen­yl]-1-(4-methyl­phen­yl)prop-2-en-1-one

Lei Wang; Li-Ying Ma; Yu-Ling Huang; Bai-Yu Zheng

doi:10.1107/S1600536809052398

. 2009 Dec 16;66(Pt 1):o174. doi: 10.1107/S1600536809052398

(E)-3-[4-(Dimethylamino)phenyl]-1-(4-methylphenyl)prop-2-en-1-one

Lei Wang ^a,^*, Li-Ying Ma ^a, Yu-Ling Huang ^a, Bai-Yu Zheng ^a

PMCID: PMC2980133 PMID: 21580060

Abstract

In the title compound, C₁₈H₁₉NO, the dihedral angle between 4-methylphenyl and 4-(dimethylamino)phenyl rings is 45.5 (3)°. The C—C=C—C torsion angle of 173.8 (3)° indicates that the molecule adopts an E configuration. The dimethylamino group is nearly coplanar with the attached benzene ring, making a dihedral angle of 2.7 (3)°. Weak intermolecular C—H⋯π interactions are observed in the crystal structure.

Related literature

The title compound is a chalcone derivative; for the biological activiy of chalcones, see: Modzelewska et al. (2006 ▶); Opletalova & Sedivy (1999 ▶); Lin et al. (2002 ▶); Hsieh et al. (1998 ▶); Lunardi et al. (2003 ▶); Tang et al. (2008 ▶). For the organic non-linear optical properties of chalcones, see: Indira et al. (2002 ▶); Ravindra et al. (2009 ▶). For related structures, see: Wang et al. (2004 ▶); Yang et al. (2006 ▶).

Experimental

Crystal data

C₁₈H₁₉NO
M _r = 265.34
Orthorhombic,
a = 7.276 (2) Å
b = 11.567 (3) Å
c = 17.642 (5) Å
V = 1484.8 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 193 K
0.59 × 0.35 × 0.18 mm

Data collection

Rigaku Mercury diffractometer
16704 measured reflections
1958 independent reflections
1846 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.136
S = 1.31
1958 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052398/xu2690sup1.cif

e-66-0o174-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052398/xu2690Isup2.hkl

e-66-0o174-Isup2.hkl^{(96.4KB, hkl)}

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 C7–C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1ⁱ	0.95	2.94	3.697 (3)	138
C9—H9⋯Cg2ⁱⁱ	0.95	2.93	3.712 (3)	141
C16—H16B⋯Cg2ⁱⁱⁱ	0.98	2.70	3.643 (3)	161

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

Acknowledgments

The authors are grateful to Binzhou Medical University for financial support (grant No. BY2007KJ57).

supplementary crystallographic information

Comment

Chalcones are open chain flavonoids which consist of two substituted benzene rings bridged by a prop-2-en-1-one group. They are renowned for their broad biological activities (Opletalova & Sedivy, 1999), such as anticancer (Modzelewska et al., 2006), antitubercular (Lin et al., 2002), anti-inflammatory (Hsieh et al., 1998), trypanocidal (Lunardi et al., 2003) and antibacterial properties (Tang et al. 2008). In addition, chalcones are also finding applications as organic non-linear optical (NLO) materials for their excellent blue light transmittance and good crystal stabitily (Indira et al., 2002; Ravindra et al., 2009). As a part of our searches for NLO materials based on chalcones (Wang, et al., 2004; Yang, et al., 2006), the title compound (I) was synthesized and its crystal structure is reported. The crystal should exhibit second-order NLO properties, because it crystallizes in a non-centrosymmetric space group.

In the title compound(I) (Fig.1), the molecule adopts an E configuration with respect to C13═C14 double bond [1.340 (4) Å]: the torsion angle C1—C13—C14—C15=173.8 (3)°. The dihedral angle between the C1—C6 ring (Plane A) and the C7—C12 ring (Plane B) is 45.5 (3)°, showing the two phenyl rings are rotated oppositely with respect to the enone segment. The mean plane of C1—C13=C14—C15 (Plane C) makes dihedral angles of 8.7 (3)° and 36.7 (4)° with plane A and plane B, respectively. The phenone O1 atom deviates from plane C by 0.240 (3) Å, suggesting C=O is not coplanar with Plane C. The dimethylamino group (Plane D) is nearly coplanar with the phenyl ring to which it is bound. The dehedral angel beween plane A and plane D is 2.7 (3)°. While no classical hydrogen bonds are present, weak intermolecular C—H···π interactions are observed, which contribute to the stability of crystal packing (Table 1).

Experimental

The synthesis of the title compound was carried out by adding an aqueous solution of sodium hydroxide (10%, 10 ml) to a solution of 4-methylacetophenone (0.02 mol) and 4-(dimethylamino)benzaldehyde (0.02 mol). The reaction mixture was stirred for 5 h at room temperature and then neutralized with HCl solution (10%). The product was recrystallized three times from ethanol (95%). Crystals suitable for X-ray analysis were grown by slow evaporation of the acetone solution at room temperature.