1-[Bis(4-fluoro­phen­yl)meth­yl]-4-[2-(2-methyl­phen­oxy)eth­yl]piperazine

Zhao-Hui Dai; Yan Zhong; Bin Wu

doi:10.1107/S1600536812010744

. 2012 Mar 17;68(Pt 4):o1077. doi: 10.1107/S1600536812010744

1-[Bis(4-fluorophenyl)methyl]-4-[2-(2-methylphenoxy)ethyl]piperazine

Zhao-Hui Dai ^a, Yan Zhong ^b, Bin Wu ^a,^*

PMCID: PMC3344032 PMID: 22589941

Abstract

In the title molecule, C₂₆H₂₈F₂N₂O, the piperazine ring adopts a chair conformation, with the N-bonded substituents in equatorial orientations. The dihedral angle between the fluorobenzene rings is 69.10 (15).

Related literature

For related structures and background to 1-(bis(4-fluorophenyl)methyl)piperazine derivatives, see: Wu et al. (2008 ▶); Dayananda et al. (2012 ▶); Zhong et al. (2011 ▶).

Experimental

Crystal data

C₂₆H₂₈F₂N₂O
M _r = 422.50
Monoclinic,
a = 10.021 (2) Å
b = 15.203 (3) Å
c = 15.868 (3) Å
β = 100.54 (3)°
V = 2376.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonious CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968) ▶ T _min = 0.976, T _max = 0.992
4618 measured reflections
4355 independent reflections
2404 reflections with I > 2σ(I)
R _int = 0.040
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.191
S = 1.03
4355 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010744/hb6677sup1.cif

e-68-o1077-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010744/hb6677Isup2.hkl

e-68-o1077-Isup2.hkl^{(213.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010744/hb6677Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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 of 1-(bis(4-fluorophenyl)methyl)piperazine derivatives (Wu et al., 2008; Zhong et al., 2011), 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 (Zhong et al., 2011). The piperazine ring adopts a chair conformation with puchering parameters Q = 0.591 (3), Theta = 1.7 (3), Phi = 333 (6). The dihedral angle between the fluorobenzene rings is 69.10 (15).

Experimental

A mixture of 1-(2-bromoethoxy)-2-methylbenzene (10 mmol), 1-(bis(4-fluorophenyl)methyl)piperazine (15 mmol) and triethylamine (5 ml) were mixed along with 40 ml acetonitrile and then refluxed for about 24 h. The progress of the reaction was monitored by TLC. After confirming that the reaction was completed, the solvent was removed under reduced pressure. The resultant mixture was cooled. The solid, 1-(bis(4-fluorophenyl)methyl)-4-(2-(2-methylphenoxy)ethyl)piperazine obtained was filtered and was recrystallized from ethanol. The colorless blocks of the title compound were grown in ethanol by a slow evaporation at room temperature.