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

Yan Zhong; Xiao-Ping Zhang; Bin Wu

doi:10.1107/S1600536812012767

. 2012 Mar 31;68(Pt 4):o1259. doi: 10.1107/S1600536812012767

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

Yan Zhong ^a, Xiao-Ping Zhang ^b, Bin Wu ^c,^*

PMCID: PMC3344185 PMID: 22606188

Abstract

In the molecule of the title compound, C₃₁H₃₆N₂O₅, the piperazine ring displays a chair conformation. The dihedral angle between the benzene rings of the bis(4-methoxyphenyl)methyl group is 83.42 (15)°. In the crystal, centrosymmetrically related molecules are linked through pairs of C—H⋯O hydrogen bonds into dimers, generating an R ₂ ²(10) ring motif. The dimers are further connected into chains parallel to [2-10] by C—H⋯O hydrogen bonds involving the methoxy groups.

Related literature

For a related structure and background to cinnamic acid derivatives, see: Teng et al. (2011 ▶); Zhong et al. (2012 ▶). For synthetic details, see: Wu et al. (2008 ▶).

Experimental

Crystal data

C₃₁H₃₆N₂O₅
M _r = 516.62
Triclinic,
a = 8.7450 (17) Å
b = 11.635 (2) Å
c = 13.967 (3) Å
α = 84.07 (3)°
β = 78.80 (3)°
γ = 80.48 (3)°
V = 1371.1 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.975, T _max = 0.992
5385 measured reflections
5029 independent reflections
2919 reflections with I > 2σ(I)
R _int = 0.024
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.185
S = 1.00
5029 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012767/rz2721sup1.cif

e-68-o1259-sup1.cif^{(25.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012767/rz2721Isup2.hkl

e-68-o1259-Isup2.hkl^{(246.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012767/rz2721Isup3.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
C17—H17A⋯O2ⁱ	0.97	2.44	3.286 (4)	146
C22—H22A⋯O3ⁱⁱ	0.93	2.60	3.476 (3)	157

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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 Jiangsu Province (No. BK2010538).

supplementary crystallographic information

Comment

As a continuation of our study on the characterization of cinnamic acid derivatives (Teng et al., 2011; Zhong & Wu, 2012), we present here the crystal structure title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related compounds (Teng et al., 2011; Zhong et al., 2012). The molecule exists in an E configulation with respect to the C21═C22 ethene bond [1.325 (4) Å]. The piperazine ring adopts a chair conformation with puckering parameters Q = 0.569 (3) Å, θ = 4.9 (3)° and φ = 4(4)°. In the crystal (Fig. 2), centrosymmetrically related molecules are linked by intermolecular C—H···O hydrogen bonds into dimers (Table 1), generating an R²₂(10) ring motif. The dimers are further connected into chains parallel to the [2 -1 0] direction by intermolecular C—H···O hydrogen bonds involving the O2 methoxy oxygen atom.

Experimental

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(4-ethoxy-3-methoxyphenyl) acrylic acid (0.889 g; 4 mmol), thionyl chloride (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)iperazine (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 obtained was filtered and was recrystallized from ethanol. The colourless single crystals of the title compound used for X-ray diffraction studies were grown by slow evaporation at room temperature of an ethanol:ethyl acetate:chloroform (3:1:1 v/i>v/i>v) solution.