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

Yan-Bo Teng; Zhao-Hui Dai; Bin Wu

doi:10.1107/S1600536811006210

. 2011 Feb 23;67(Pt 3):o697. doi: 10.1107/S1600536811006210

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

Yan-Bo Teng ^a, Zhao-Hui Dai ^a, Bin Wu ^a,^*

PMCID: PMC3051918 PMID: 21522442

Abstract

In the title compound, C₂₈H₂₉FN₂O₃, the conformation about the ethene bond is E. The piperazine ring adopts a chair conformation. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds.

Related literature

For properties of cinnamic acid derivatives, see: Shi et al. (2005 ▶); Point et al. (1998 ▶). For synthetic procedures, see: Wu et al. (2008 ▶). For a related structure, see: Mouillé et al. (1975 ▶).

Experimental

Crystal data

C₂₈H₂₉FN₂O₃
M _r = 460.53
Monoclinic,
a = 10.235 (2) Å
b = 7.8420 (16) Å
c = 30.385 (6) Å
β = 96.65 (3)°
V = 2422.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968) ▶ T _min = 0.983, T _max = 0.991
4730 measured reflections
4463 independent reflections
2366 reflections with I > 2σ(I)
R _int = 0.031
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.170
S = 1.01
4463 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006210/pv2381sup1.cif

e-67-0o697-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006210/pv2381Isup2.hkl

e-67-0o697-Isup2.hkl^{(218.7KB, hkl)}

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
C5—H5A⋯O1ⁱ	0.93	2.28	3.131 (4)	152
C17—H17A⋯O3ⁱⁱ	0.93	2.60	3.499 (4)	163

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

Acknowledgments

This study was supported financially by grant No. BK2010538 from the Natural Science Foundation of Jiangsu Province. The authors extend special thanks to Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for the data collection.

supplementary crystallographic information

Comment

Cinnamic acid derivatives have been reported to possess many useful properties, including alpha-glucosidase inhibition, acyl-CoA inhibition, LDL-oxidation inhibition, tyrosinase inhibition, antioxidant, antimicrobial, neuroprotective activities (Shi et al., 2005; Point et al., 1998). We report here the synthesis and crystal structure of a novel cinnamic acid derivative.

In the title molecule (Fig. 1), the conformation about the ethene bond C7═C8 is E. The piperazine ring adopts a chair conformation. There are intramolecular and intermolecular C—H···O hydrogen bonds in the title compound (Fig. 2) which consilidate the crystal structure. The bond lenths and angles in the title compound agree well with the corresponding bond lengths and angles in a closely related compound, trans-cinnamyl-1-diphenylmethyl-4-piperazine (Mouillé et al., 1975).

Experimental

The synthesis follows the method of Wu et al. (2008). A mixture of (E)-3-(4-fluoro phenyl)acrylic acid (1.66 g; 10 mmol), dimethyl sulfoxide (4 ml) and dichloromethane (60 ml) was stirred for 6 h at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in acetone (60 ml) and reacted with 1-(bis(4-methoxyphenyl)methyl) piperazine (4.69 g; 15 mmol) in the presence of triethylamine (12 ml) for 5 h at room temperature. The resultant mixture was cooled. The solid thus obtained was filtered and recrystallized from ethanol to afford the title compound. Pale-yellow single crystals of the title compound suitable for X-ray diffraction studies were grown from a mixture of CHCl₃ and hexane (1:1) by slow evaporation at room temperature.