(E)-1-{4-[Bis(4-meth­oxy­phen­yl)meth­yl]piperazin-1-yl}-3-(4-methyl­phen­yl)prop-2-en-1-one

Yan Zhong; Bin Wu

doi:10.1107/S1600536811039353

. 2011 Sep 30;67(Pt 10):o2791. doi: 10.1107/S1600536811039353

(E)-1-{4-[Bis(4-methoxyphenyl)methyl]piperazin-1-yl}-3-(4-methylphenyl)prop-2-en-1-one

Yan Zhong ^a, Bin Wu ^b,^*

PMCID: PMC3201336 PMID: 22064692

Abstract

In the title molecule, C₂₉H₃₂N₂O₃, the piperazine ring has a chair conformation. The amide N atom is almost planar (bond angle sum = 359.5°), whereas the other N atom is clearly pyramidal (bond angle sum = 330.4°). The dihedral angle between the methoxybenzene rings is 81.29 (16)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds.

Related literature

For structures and properties of cinnamic acid derivatives, see: Shi et al. (2005 ▶); Qian et al. (2010 ▶). For the synthesis, see: Wu et al. (2008 ▶). For related structures, see: Mouillé et al. (1975) ▶; Teng et al. (2011 ▶).

Experimental

Crystal data

C₂₉H₃₂N₂O₃
M _r = 456.57
Monoclinic,
a = 10.114 (2) Å
b = 11.867 (2) Å
c = 21.573 (4) Å
β = 97.12 (3)°
V = 2569.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
5002 measured reflections
4718 independent reflections
2269 reflections with I > 2σ(I)
R _int = 0.037
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.189
S = 1.01
4718 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811039353/hb6419sup1.cif

e-67-o2791-sup1.cif^{(24KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039353/hb6419Isup2.hkl

e-67-o2791-Isup2.hkl^{(231.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039353/hb6419Isup3.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
C11—H11A⋯O1ⁱ	0.93	2.60	3.360 (4)	140
C22—H22A⋯O3ⁱⁱ	0.93	2.59	3.483 (4)	160

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

Acknowledgments

The authors thank Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for the diffraction measurements. This work was supported by the Natural Science Foundation of the Education Department of Jiangsu Province (No. 05KJB350084) and the Natural Science Foundation of Jiangsu Province (No. BK2010538).

supplementary crystallographic information

Comment

Recently, many compounds containing a cinnamoyl moiety have drawn much attention owing to their significant pharacological properties such as antimicrobial, anticancer and neuroprotective activities (Shi et al., 2005; Qian et al., 2010). As a part of our ongoing study of the substituent effect on the stuctures of cinnamide derivatives, we report herein the crystal structure of the title compound. The molecule of the title compound exists an E configulation with respect to the C21=C22 ethene bond [1.318 (4)] and the torsion angle C20—C21—C22—C23 = -178.7 (3). The piperazine ring adopts a chair conformation. In the crystal, moleculaes are linked by intermolecular C—H···O interactions.

Experimental

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(4-methylphenyl)acrylic acid (0.649 g; 4 mmol), dimethyl sulfoxide (2 ml) and dichloromethane (30 ml) for 6 h at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in acetone (15 ml) and reacted with 1-(bis(4-methoxyphenyl)methyl) piperazine (1.874 g; 6 mmol) in the presence of triethylamine (5 ml) for 12 h at room temperature. The resultant mixture was cooled. The solid, (E)-1-(4-(bis(4-methoxyphenyl)methyl) piperazin-1-yl)-3- (4-methylphenyl)prop-2-en-1-one obtained was filtered and was recrystallized from ethanol. The colorless single crystals of the title compound used in x-ray diffraction studies were grown in ethanol by a slow evaporation at room temperature.