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

Yan Zhong; XiaoPing Zhang; Bin Wu

doi:10.1107/S1600536811048380

. 2011 Nov 19;67(Pt 12):o3358. doi: 10.1107/S1600536811048380

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

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

PMCID: PMC3239003 PMID: 22199852

Abstract

In the title molecule, C₂₆H₂₃Br₃N₂O, the piperazine ring adopts a chair conformation and the C=C double bond has an E configuration. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For pharmacological properties of cinnamic acid derivatives, see: Shi et al. (2005 ▶); Qian et al. (2010 ▶). For the synthesis of the title compound, see: Wu et al. (2008 ▶). For a related structure, see: Teng et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₆H₂₃Br₃N₂O
M _r = 619.19
Monoclinic,
a = 9.956 (2) Å
b = 11.624 (2) Å
c = 21.310 (4) Å
β = 101.45 (3)°
V = 2417.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 5.03 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 = 0.433, T _max = 0.633
4701 measured reflections
4432 independent reflections
2081 reflections with I > 2σ(I)
R _int = 0.098
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.082
S = 1.01
4432 reflections
289 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.42 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/S1600536811048380/pv2478sup1.cif

e-67-o3358-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048380/pv2478Isup2.hkl

e-67-o3358-Isup2.hkl^{(217.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811048380/pv2478Isup3.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	2.60	3.480 (7)	159

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

supplementary crystallographic information

Comment

Recently, many compounds containing a cinnamoyl moiety have drawn much attention owing to their significant pharmacological properties such as antimicrobial, anticancer and neuroprotective activities (Shi et al., 2005; Qian et al., 2010). As a part of our ongoing study of the substituent effect on the stuctures of cinnamide derivatives, we report herein the crystal structure of the title compound.

The title compound (Fig. 1) exhibits an E configulation with respect to the C19═C20 ethene bond [1.320 (7) Å] with a torsion angle C18—C19—C20—C21 = -177.4 (6)°. The piperazine ring adopts a chair conformation with puchering parameters (Cremer & Pople, 1975) Q = 0.542 (6)Å, θ = 4.6 (6)° and φ = 157 (9)°. In the crystal, molecules are linked by intermolecular C—H···O interactions (Tab. 1, Fig. 2).

Experimental

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(4-bromophenyl)acrylic acid (0.908 g, 4 mmol), dimethyl sulfoxide (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) piperazine (2.461 g, 6 mmol) in the presence of triethylamine (5 ml) for 12 h at room temperature. The resultant mixture was cooled. The title compound thus obtained was filtered and recrystallized from ethanol. The pale-yellow single crystals of the title compound used in X-ray diffraction studies were grown from a mixture of ethanol and chloroform (2:1) by slow evaporation at room temperature.