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Volume 69 
Part 8 
Page o1344  
August 2013  

Received 16 July 2013
Accepted 22 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.136
Data-to-parameter ratio = 15.3
Details
Open access

Flunarizinium hydrogen maleate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cR. L. Fine Chem., Bangalore 560 064, India
Correspondence e-mail: jjasinski@keene.edu

In the cation of the title salt {systematic name: 4-[bis(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium hydrogen maleate}, C26H27F2N2+·C4H3O4-, the protonated piperazine ring is in a chair conformation. The dihedral angle between the 4-fluorophenyl rings is 68.2 (2)°. An intramolecular O-H...O hydrogen bond occurs in the anion. In the crystal, N-H...O, C-H...O and C-H...F interactions are observed, which link the ions into [001] chains.

Related literature

For backgorund to flunarizine, see: Amery (1983[Amery, W. K. (1983). Headache, 23, 70-74.]); Holmes et al. (1984[Holmes, B., Brogden, R. N., Heel, R. C., Speight, T. M. & Avery, G. S. (1984). Drugs. 27, 6-44.]). For related structures, see: Jasinski, Butcher et al. (2010[Jasinski, J. P., Butcher, R. J., Hakim Al-Arique, Q. N. M., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o366-o367.]); Jasinski, Pek et al. (2010[Jasinski, J. P., Pek, A. E., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o2012-o2013.]); Kavitha et al. (2013[Kavitha, C. N., Yathirajan, H. S., Narayana, B., Gerber, T., van Brecht, B. & Betz, R. (2013). Acta Cryst. E69, o260-o261.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C26H27F2N2+·C4H3O4-

  • Mr = 520.56

  • Monoclinic, P 21 /c

  • a = 22.1215 (5) Å

  • b = 10.8620 (2) Å

  • c = 11.3215 (2) Å

  • [beta] = 98.879 (2)°

  • V = 2687.77 (9) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.79 mm-1

  • T = 173 K

  • 0.42 × 0.38 × 0.26 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.871, Tmax = 1.000

  • 17207 measured reflections

  • 5260 independent reflections

  • 4484 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.136

  • S = 1.03

  • 5260 reflections

  • 344 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1S-H1S...O4S 0.82 1.63 2.451 (2) 177
N1-H1...O3S 0.91 1.83 2.7190 (18) 165
C1-H1B...O2Si 0.97 2.51 3.354 (2) 146
C26-H26...O3Sii 0.93 2.53 3.278 (2) 138
C2S-H2S...O4Siii 0.93 2.46 3.386 (2) 171
C23-H23...F1iv 0.93 2.53 3.342 (2) 145
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7110 ).


Acknowledgements

CNK thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to do research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Amery, W. K. (1983). Headache, 23, 70-74.  [CrossRef] [ChemPort] [PubMed]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Holmes, B., Brogden, R. N., Heel, R. C., Speight, T. M. & Avery, G. S. (1984). Drugs. 27, 6-44.  [CrossRef] [ChemPort] [PubMed]
Jasinski, J. P., Butcher, R. J., Hakim Al-Arique, Q. N. M., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o366-o367.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Jasinski, J. P., Pek, A. E., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o2012-o2013.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kavitha, C. N., Yathirajan, H. S., Narayana, B., Gerber, T., van Brecht, B. & Betz, R. (2013). Acta Cryst. E69, o260-o261.  [CrossRef] [ChemPort] [IUCr Journals]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1344  [ doi:10.1107/S1600536813020291 ]

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