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Volume 69 
Part 1 
Pages o142-o143  
January 2013  

Received 9 December 2012
Accepted 18 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.121
Data-to-parameter ratio = 15.5
Details
Open access

Cinnarizinium fumarate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: jjasinski@keene.edu

In the title salt {systematic name: 4-diphenylmethyl-1-[(E)-3-phenylprop-2-en-1-yl]piperazin-1-ium (2Z)-3-carboxyprop-2-enoate}, C26H29N2+·C4H3O4-, the piperazine ring in the cation adopts a distorted chair conformation and contains a positively charged N atom with quaternary character. The dihedral angle between the mean planes of the phenyl rings of the diphenylmethyl group is 74.2 (7)° and those between these rings and the phenyl ring of the 3-phenylprop-2-en-1-yl group are 12.7 (9) and 80.6 (8)°. In the crystal, N-H...O and O-H...O hydrogen bonds form chains along [001]. Weak C-H...O interactions connect parallel chains along [010], forming layers perpendicular to the a-axis direction.

Related literature

For cinnarizine as a calcium channel blocker, see: Terland & Flatmark (1999[Terland, O. & Flatmark, T. (1999). Neuropharmacology, 38, 879-882.]), as a nootropic drug, see: Towse (1980[Towse, G. (1980). J. Laryngol. Otol. 94, 1009-1015.]) and for a clinical evaluation in various allergic disorders, see: Barrett & Zolov (1960[Barrett, R. J. & Zolov, B. (1960). J. Maine Med. Assoc. 51, 454-457.]). For related structures, see: Bertolasi et al. (1980[Bertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 1975-1977.]); Dayananda et al. (2012[Dayananda, A. S., Yathirajan, H. S., Gerber, T., Hosten, E. & Betz, R. (2012). Acta Cryst. E68, o1165-o1166.]); Jasinski et al. (2011[Jasinski, J. P., Butcher, R. J., Siddegowda, M. S., Yathirajan, H. S. & Chidan Kumar, C. S. (2011). Acta Cryst. E67, o500-o501.]); Mouillé et al. (1975[Mouillé, Y., Cotrait, M., Hospital, M. & Marsau, P. (1975). Acta Cryst. B31, 1495-1496.]); Siddegowda et al. (2011[Siddegowda, M. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Swamy, M. T. (2011). Acta Cryst. E67, o2296.]); Song et al. (2012[Song, Y., Chidan Kumar, C. S., Nethravathi, G. B., Naveen, S. & Li, H. (2012). Acta Cryst. E68, o1747.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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
  • C26H29N2+·C4H3O4-

  • Mr = 484.58

  • Monoclinic, P 21 /c

  • a = 21.9467 (4) Å

  • b = 10.43729 (18) Å

  • c = 11.20623 (19) Å

  • [beta] = 90.0458 (15)°

  • V = 2566.95 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 123 K

  • 0.60 × 0.30 × 0.25 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED and CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]) Tmin = 0.732, Tmax = 1.000

  • 9777 measured reflections

  • 5146 independent reflections

  • 4289 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.121

  • S = 1.02

  • 5146 reflections

  • 333 parameters

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

  • [Delta][rho]max = 0.27 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
N2-H1N...O4 0.943 (19) 1.740 (19) 2.6750 (15) 170.9 (17)
O1-H1O1...O4i 0.94 (3) 1.70 (3) 2.6270 (15) 168 (2)
C18-H18B...O3ii 0.97 2.56 3.3839 (18) 143
C15-H15A...O3ii 0.97 2.47 3.3463 (18) 151
C15-H15B...O2iii 0.97 2.46 3.1941 (19) 132
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}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2527 ).


Acknowledgements

CNK thanks the University of Mysore for research facilities. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2011). 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.
Barrett, R. J. & Zolov, B. (1960). J. Maine Med. Assoc. 51, 454-457.  [PubMed]
Bertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 1975-1977.  [CrossRef] [details] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dayananda, A. S., Yathirajan, H. S., Gerber, T., Hosten, E. & Betz, R. (2012). Acta Cryst. E68, o1165-o1166.  [CrossRef] [details]
Jasinski, J. P., Butcher, R. J., Siddegowda, M. S., Yathirajan, H. S. & Chidan Kumar, C. S. (2011). Acta Cryst. E67, o500-o501.  [CSD] [CrossRef] [details]
Mouillé, Y., Cotrait, M., Hospital, M. & Marsau, P. (1975). Acta Cryst. B31, 1495-1496.  [CrossRef] [details] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siddegowda, M. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Swamy, M. T. (2011). Acta Cryst. E67, o2296.  [CSD] [CrossRef] [details]
Song, Y., Chidan Kumar, C. S., Nethravathi, G. B., Naveen, S. & Li, H. (2012). Acta Cryst. E68, o1747.  [CSD] [CrossRef] [details]
Terland, O. & Flatmark, T. (1999). Neuropharmacology, 38, 879-882.  [CrossRef] [PubMed] [ChemPort]
Towse, G. (1980). J. Laryngol. Otol. 94, 1009-1015.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o142-o143   [ doi:10.1107/S1600536812051239 ]

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