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

Zhong, Y.; Zhang, X.P.; Wu, B.

doi:10.1107/S1600536811052123

Volume 68
Part 1
Page o122
January 2012

Received 2 December 2011
Accepted 2 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R = 0.077
wR = 0.145
Data-to-parameter ratio = 16.0
Details

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

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

^aSchool of Chemistry and Chemical Engineering, Southeast University, Sipailou No. 2 Nanjing, Nanjing 210096, People's Republic of China,^bCentre of Laboratory Animals, Nanjing medical University, Hanzhong Road No. 140 Nanjing, Nanjing 210029, People's Republic of China, and ^cSchool of Pharmacy, Nanjing Medical University, Hanzhong Road No. 140 Nanjing, Nanjing 210029, People's Republic of China
Correspondence e-mail: wubin@njmu.edu.cn

In the title molecule, C₂₉H₃₀Br₂N₂O₃, the piperazine ring has a chair conformation and the C=C double bond has an E conformation. The dihedral angle between the bromobenzene rings is 79.1 (3)°. In the crystal, molecules are linked through C-HO and C-HBr hydrogen bonds.

Related literature

For a related structure and background to cinnamic acid derivatives, see: Teng et al. (2011); Zhong et al. (2011). For further synthetic details, see: Wu et al. (2008). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₉H₃₀Br₂N₂O₃
M_r = 614.37
Triclinic, $[P \overline 1]$
a = 8.5520 (17) Å
b = 10.355 (2) Å
c = 16.361 (3) Å
= 92.85 (3)°
= 100.52 (3)°
= 95.25 (3)°
V = 1415.3 (5) Å³
Z = 2
Mo K radiation
= 2.90 mm^-1
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.595, T_max = 0.761
5569 measured reflections
5190 independent reflections
2233 reflections with I > 2(I)
R_int = 0.098
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.077
wR(F²) = 0.145
S = 1.01
5190 reflections
325 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12AO1ⁱ	0.93	2.55	3.358 (8)	145
C20-H20AO1ⁱⁱ	0.93	2.57	3.461 (8)	161
C16-H16BBr1ⁱⁱⁱ	0.97	2.79	3.562 (7)	137
Symmetry codes: (i) x-1, y, z; (ii) -x+3, -y+1, -z; (iii) -x+2, -y+1, -z+1.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: SU2344 ).

Acknowledgements

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).

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Teng, Y.-B., Dai, Z.-H. & Wu, B. (2011). Acta Cryst. E67, o697.
Wu, B., Zhou, L. & Cai, H.-H. (2008). Chin. Chem. Lett. 19, 1163-1166.
Zhong, Y., Zhang, X. P. & Wu, B. (2011). Acta Cryst. E67, o3358.

organic compounds