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Volume 69 
Part 2 
Pages o260-o261  
February 2013  

Received 9 November 2012
Accepted 8 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.081
Data-to-parameter ratio = 10.4
Details
Open access

4-[Bis(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium 3-carboxypropanoate

aUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India,bMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title salt, C26H27F2N2+·C4H5O4-, the piperazine N atom bearing the vinylic substituent is protonated. The piperazine ring adopts a chair conformation. In ther crystal, the succinate monoanions are connected via short O-H...O hydrogen bonds between the carboxylic acid and carboxylate groups into undulating chains extending along [001] and the flunarizinium monocations are attached to these chains via N+-H...O- hydrogen bonds. C-H...O interactions connect these chains into a three-dimensional network. The shortest centroid-centroid distance of 3.7256 (10) Å was found between one of the fluorinated benzene rings and the non-fluorinated phenyl ring in the neighbouring molecule related by a glide plane.

Related literature

For pharmaceutical properties of flunarizine, see: Holmes et al. (1984[Holmes, B., Brogden, R. N., Heel, R. C., Speight, T. M. & Avery, G. S. (1984). Drugs, 27, 6-44.]); Amery (1983[Amery, W. K. (1983). Headache, 23, 70-74.]) and of piperazine derivatives, see: Brockunier et al. (2004[Brockunier, L. L., He, J., Colwell, L. F. Jr, Habulihaz, B., He, H., Leiting, B., Lyons, K. A., Marsilio, F., Patel, R. A., Teffera, Y., Wu, J. K., Thornberry, N. A., Weber, A. E. & Parmee, E. R. (2004). Bioorg. Med. Chem. Lett. 14, 4763-4766.]); Bogatcheva et al. (2006[Bogatcheva, E., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Barbosa, F., Einck, L., Nacy, C. A. & Protopopova, M. (2006). J. Med. Chem. 49, 3045-3048.]); Elliott (2011[Elliott, S. (2011). Drug. Test. Anal. 3, 430-438.]). For related structures, see: Betz et al. (2011a[Betz, R., Gerber, T., Hosten, E., Dayananda, A. S. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o2783-o2784.],b[Betz, R., Gerber, T., Hosten, E., Dayananda, A. S., Yathirajan, H. S. & Narayana, B. (2011b). Acta Cryst. E67, o2587-o2588.]); Dayananda et al. (2012a[Dayananda, A. S., Dutkiewicz, G., Yathirajan, H. S., Ramesha, A. R. & Kubicki, M. (2012a). Acta Cryst. E68, o2817.],b[Dayananda, A. S., Yathirajan, H. S., Keeley, A. C. & Jasinski, J. P. (2012b). Acta Cryst. E68, o2237.]); Fillers & Hawkinson (1982[Fillers, J. P. & Hawkinson, S. W. (1982). Acta Cryst. B38, 3041-3045.]); Vanier & Brisse (1983[Vanier, M. & Brisse, F. (1983). Acta Cryst. C39, 912-914.]). For puckering analysis of six-membered rings, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Boeyens (1978[Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C26H27F2N2+·C4H5O4-

  • Mr = 522.58

  • Monoclinic, P c

  • a = 10.7824 (2) Å

  • b = 10.6270 (2) Å

  • c = 11.2364 (2) Å

  • [beta] = 91.678 (1)°

  • V = 1286.97 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 200 K

  • 0.56 × 0.29 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS . Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.947, Tmax = 0.985

  • 16870 measured reflections

  • 3619 independent reflections

  • 3524 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.081

  • S = 1.03

  • 3619 reflections

  • 348 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H72...O1 0.96 (2) 1.73 (2) 2.6795 (16) 174 (2)
O3-H3...O1i 0.84 1.84 2.6564 (16) 162
C4-H4A...O4ii 0.99 2.58 3.287 (3) 128
C4-H4B...O2iii 0.99 2.39 3.3167 (19) 155
C25-H25...O2iv 0.95 2.53 3.4168 (19) 155
C12-H12...Cgv 0.95 2.81 3.7511 (17) 170
Symmetry codes: (i) [x, -y+2, z+{\script{1\over 2}}]; (ii) [x, -y+2, z-{\script{1\over 2}}]; (iii) [x, -y+1, z-{\script{1\over 2}}]; (iv) [x+1, -y+1, z-{\script{1\over 2}}]; (v) [x, -y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2534 ).


Acknowledgements

CNK thanks the University of Mysore for research facilities and the Principal of Maharani's Science College for Women for permission to do research.

References

Amery, W. K. (1983). Headache, 23, 70-74.  [CrossRef] [ChemPort] [PubMed]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Betz, R., Gerber, T., Hosten, E., Dayananda, A. S. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o2783-o2784.  [CSD] [CrossRef] [details]
Betz, R., Gerber, T., Hosten, E., Dayananda, A. S., Yathirajan, H. S. & Narayana, B. (2011b). Acta Cryst. E67, o2587-o2588.  [CSD] [CrossRef] [details]
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.  [CrossRef]
Bogatcheva, E., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Barbosa, F., Einck, L., Nacy, C. A. & Protopopova, M. (2006). J. Med. Chem. 49, 3045-3048.  [ISI] [CrossRef] [PubMed] [ChemPort]
Brockunier, L. L., He, J., Colwell, L. F. Jr, Habulihaz, B., He, H., Leiting, B., Lyons, K. A., Marsilio, F., Patel, R. A., Teffera, Y., Wu, J. K., Thornberry, N. A., Weber, A. E. & Parmee, E. R. (2004). Bioorg. Med. Chem. Lett. 14, 4763-4766.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). SADABS . Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dayananda, A. S., Dutkiewicz, G., Yathirajan, H. S., Ramesha, A. R. & Kubicki, M. (2012a). Acta Cryst. E68, o2817.  [CSD] [CrossRef] [details]
Dayananda, A. S., Yathirajan, H. S., Keeley, A. C. & Jasinski, J. P. (2012b). Acta Cryst. E68, o2237.  [CSD] [CrossRef] [details]
Elliott, S. (2011). Drug. Test. Anal. 3, 430-438.  [CrossRef] [ChemPort] [PubMed]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fillers, J. P. & Hawkinson, S. W. (1982). Acta Cryst. B38, 3041-3045.  [CrossRef] [ISI] [details]
Holmes, B., Brogden, R. N., Heel, R. C., Speight, T. M. & Avery, G. S. (1984). Drugs, 27, 6-44.  [CrossRef] [ChemPort] [PubMed] [ISI]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vanier, M. & Brisse, F. (1983). Acta Cryst. C39, 912-914.  [CrossRef] [details]


Acta Cryst (2013). E69, o260-o261   [ doi:10.1107/S1600536813000706 ]

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