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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 [sigma](C-C) = 0.009 Å
R = 0.077
wR = 0.145
Data-to-parameter ratio = 16.0
Details
Open access

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

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-H...O and C-H...Br hydrogen bonds.

Related literature

For a related structure and background to cinnamic acid derivatives, see: Teng et al. (2011[Teng, Y.-B., Dai, Z.-H. & Wu, B. (2011). Acta Cryst. E67, o697.]); Zhong et al. (2011[Zhong, Y., Zhang, X. P. & Wu, B. (2011). Acta Cryst. E67, o3358.]). For further synthetic details, see: Wu et al. (2008[Wu, B., Zhou, L. & Cai, H.-H. (2008). Chin. Chem. Lett. 19, 1163-1166.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C29H30Br2N2O3

  • Mr = 614.37

  • Triclinic, [P \overline 1]

  • a = 8.5520 (17) Å

  • b = 10.355 (2) Å

  • c = 16.361 (3) Å

  • [alpha] = 92.85 (3)°

  • [beta] = 100.52 (3)°

  • [gamma] = 95.25 (3)°

  • V = 1415.3 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.90 mm-1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.595, Tmax = 0.761

  • 5569 measured reflections

  • 5190 independent reflections

  • 2233 reflections with I > 2[sigma](I)

  • Rint = 0.098

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.145

  • S = 1.01

  • 5190 reflections

  • 325 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12A...O1i 0.93 2.55 3.358 (8) 145
C20-H20A...O1ii 0.93 2.57 3.461 (8) 161
C16-H16B...Br1iii 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[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Teng, Y.-B., Dai, Z.-H. & Wu, B. (2011). Acta Cryst. E67, o697.  [CSD] [CrossRef] [details]
Wu, B., Zhou, L. & Cai, H.-H. (2008). Chin. Chem. Lett. 19, 1163-1166.  [CrossRef] [ChemPort]
Zhong, Y., Zhang, X. P. & Wu, B. (2011). Acta Cryst. E67, o3358.  [CrossRef] [details]


Acta Cryst (2012). E68, o122  [ doi:10.1107/S1600536811052123 ]

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