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

Yan Zhong; Bin Wu

doi:10.1107/S1600536812024130

. 2012 May 31;68(Pt 6):o1975. doi: 10.1107/S1600536812024130

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

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

PMCID: PMC3379522 PMID: 22719720

Abstract

In the title compound, C₂₈H₂₈F₂N₂O₂, the piperazine ring has a chair conformation with the pendant N—C bonds in equatorial orientations. The C=C double bond has an E conformation and the dihedral angle between the fluorobenzene rings is 70.8 (3)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯F hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₂₈H₂₈F₂N₂O₂
M _r = 462.52
Orthorhombic,
a = 8.8550 (18) Å
b = 12.827 (3) Å
c = 22.432 (5) Å
V = 2547.9 (9) Å³
Z = 4
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
5217 measured reflections
2677 independent reflections
1328 reflections with I > 2σ(I)
R _int = 0.092
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.160
S = 1.00
2677 reflections
307 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.12 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/S1600536812024130/hb6812sup1.cif

e-68-o1975-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024130/hb6812Isup2.hkl

e-68-o1975-Isup2.hkl^{(131.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812024130/hb6812Isup3.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
C5—H5A⋯O1ⁱ	0.93	2.44	3.316 (6)	156
C15—H15A⋯F2ⁱⁱ	0.97	2.36	3.241 (6)	150
C25—H25A⋯F1ⁱⁱⁱ	0.93	2.55	3.166 (7)	124

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

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 (grant No. BK2010538).

supplementary crystallographic information

Comment

As a continuation of our study of cinnamic acid derivatives (Teng et al., 2011; Zhong et al., 2012), we present here the 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 of (I) exists an E configulation with respect to the C19=C20 ethene bond [1.296 (6)]. The piperazine ring adopts a chair conformation with puchering parameters Q = 0.498 (6), Theta = 8.6 (6), Phi = 136 (4). The molecular structure is stabilized by intramolecular C—H···O and C—H···F hydrogen bonds. In the crystal, molecules are linked by intermolecular C—H···O and C—H···F hydrogen bonds.

Experimental

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(2-ethoxyphenyl)acrylic acid (0.769 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-((2-fluorophenyl)(4-fluorophenyl)methyl)piperazine (1.730 g; 6 mmol) in the presence of triethylamine (5 ml) for 12 h at room temperature. The resultant mixture was cooled. The solid, (E)-3-(2-ethoxyphenyl)-1-(4-((2- fluorophenyl)(4-fluorophenyl)methyl)piperazin-1-yl)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.