(E)-1-(4-Benzhydrylpiperazin-1-yl)-3-(3,4-dieth­oxy­phen­yl)prop-2-en-1-one ethanol monosolvate

Yan Zhong; Bin Wu

doi:10.1107/S1600536811042267

. 2011 Oct 22;67(Pt 11):o2992. doi: 10.1107/S1600536811042267

(E)-1-(4-Benzhydrylpiperazin-1-yl)-3-(3,4-diethoxyphenyl)prop-2-en-1-one ethanol monosolvate

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

PMCID: PMC3247394 PMID: 22220012

Abstract

In the title compound, C₃₀H₃₄N₂O₃·C₂H₆O, the piperazine ring adopts a chair conformation and the ethene bond exhibits an E conformation. In the crystal, the two components are linked by an O—H⋯O hydrogen bond.

Related literature

For biological properties of cinnamic acid derivatives, see: Shi et al. (2005 ▶); Qian et al. (2010 ▶). For the synthesis, see: Wu et al. (2008 ▶). For a related structure, see: Teng et al. (2011 ▶).

Experimental

Crystal data

C₃₀H₃₄N₂O₃·C₂H₆O
M _r = 516.66
Triclinic,
a = 7.9590 (16) Å
b = 12.039 (2) Å
c = 16.298 (3) Å
α = 104.27 (3)°
β = 100.09 (3)°
γ = 100.02 (3)°
V = 1450.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 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 = 0.977, T _max = 0.992
5753 measured reflections
5335 independent reflections
3341 reflections with I > 2.0σ(I)
R _int = 0.019
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.166
S = 1.00
5335 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.25 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: SHELXL97 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042267/pv2451sup1.cif

e-67-o2992-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042267/pv2451Isup2.hkl

e-67-o2992-Isup2.hkl^{(261.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042267/pv2451Isup3.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
O4—H4B⋯O3	0.82	1.94	2.765 (3)	177

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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 Education Department of Jiangsu Province (No. 05KJB350084) and the Natural Science Foundation of Jiangsu Province (No. BK2010538).

supplementary crystallographic information

Comment

There has been much research interest in cinnamic acid and its derivatives due to their biological activities (Shi et al., 2005; Qian et al., 2010). In this work, we report the crystal structure of the title compound. The title compound (Fig. 1) exists an E-conformation with respect to the C11═C12 ethene bond [1.327 (3) Å] and the torsion angle C3—C11—C12—C13 is 175.4 (2)°. The piperazine ring adopts a chair conformation. The molecular structure is stabilized by intramolecular O—H···O and C—H···O interactions between the title compound and the ethanol molecule of solvation.

Experimental

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(3,4-diethoxyphenyl)acrylic acid (0.945 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-benzhydrylpiperazine (1.514 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-(benzhydrylpiperazin-1-yl)-3-(3,4-diethoxyphenyl)prop-2-en-1- one obtained was filtered and was recrystallized from ethanol. The pale-yellow single crystals of the title compound used in X-ray diffraction studies were grown in ethanol by slow evaporation at room temperature.