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

Yan Zhong; XiaoPing Zhang; Bin Wu

doi:10.1107/S1600536812003820

. 2012 Feb 4;68(Pt 3):o605. doi: 10.1107/S1600536812003820

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

Yan Zhong ^a, XiaoPing Zhang ^b, Bin Wu ^c,^*

PMCID: PMC3297328 PMID: 22412518

Abstract

In the title compound, C₂₇H₂₆Br₂N₂O, the piperazine ring adopts a chair conformation with the N—C bonds in equatorial orientations. The C=C double bond has an E configuration. The dihedral angle between the bromobenzene rings is 83.0 (4)°. In the crystal, inversion dimers linked through pairs of C—H⋯O hydrogen bonds generate R ₂ ²(10) loops.

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

C₂₇H₂₆Br₂N₂O
M _r = 554.32
Monoclinic,
a = 10.050 (2) Å
b = 11.622 (2) Å
c = 21.259 (4) Å
β = 101.72 (3)°
V = 2431.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.36 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 = 0.553, T _max = 0.730
4720 measured reflections
4452 independent reflections
1998 reflections with I > 2σ(I)
R _int = 0.097
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.075
wR(F ²) = 0.155
S = 1.00
4452 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: XCAD4 (Harms & Wocadlo, 1995 ▶); data reduction: XCAD4; 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/S1600536812003820/hb6616sup1.cif

e-68-0o605-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003820/hb6616Isup2.hkl

e-68-0o605-Isup2.hkl^{(218.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812003820/hb6616Isup3.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
C20—H20A⋯Oⁱ	0.93	2.55	3.445 (10)	162

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Symmetry code: (i) Inline graphic .

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 [1.317 (10)]. The piperazine ring adopts a chair conformation with puchering parameters Q = 0.574 (8), Theta = 5.0 (7), Phi = 2(10). In the crystal, molecules are linked by C—H···O hydrogen bonds to form inversion dimers.

Experimental

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(4-methylphenyl) acrylic acid (0.649 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-bromophenyl)methyl)iperazine (2.461 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-(bis(4-bromophenyl)methyl)piperazin-1-yl) -3-(4-methylphenyl)prop-2-en-1-one obtained was filtered and was recrystallized from ethanol. Colourless blocks were grown from an ethanol:ethyl acetate (1:1) solution by slow evaporation at room temperature.