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Volume 69 
Part 4 
Pages o485-o486  
April 2013  

Received 18 January 2013
Accepted 8 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.054
wR = 0.140
Data-to-parameter ratio = 14.2
Details
Open access

Cinnarizinium bis(p-toluenesulfonate) dihydrate

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

The asymmetric unit of the title salt [systematic name: 1-benzhydryl-4-cinnamylpiperazine-1,4-diium bis(p-toluenesulfonate) dihydrate], C26H30N22+·2C7H7O3S-·2H2O, consists of a diprotonated cinnarizinium cation hydrogen bonded through two water molecules to two independent p-toluenesulfonate anions, one which is disordered over two sets of sites in a 0.793 (3):0.207 (3) ratio. In the cation, the piperazine ring adopts a chair configuration and contains two positively charged N atoms with quarternery character. The dihedral angle between the two benzene rings in the benzhydryl group is 71.8 (1)°. The benzene ring flanked opposite the piperazine ring is twisted by 75.9 (9) and 8.8 (3)° from these two benzene rings. In the crystal, the [N-H...Owater-H...O([pdbond]S)]2 hydrogen-bonded asymmetric unit is connected by further O-H...O hydrogen bonds linking the components into chains along [100].

Related literature

For cinnarizine (systematic name: 1-benzhydryl-4-cinnamyl-piperazine) as a nootropic drug, see: Towse (1980[Towse, G. (1980). J. Laryngol. Otol. 94, 1009-1015.]). For cinnarizine in 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.]); Smith et al. (2001[Smith, G., Bott, R. C. & Wermuth, U. D. (2001). Acta Cryst. E57, o640-o642.]); 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
  • C26H30N22+·2C7H7O3S-·2H2O

  • Mr = 748.92

  • Monoclinic, P 21 /n

  • a = 10.0845 (2) Å

  • b = 14.6026 (3) Å

  • c = 25.8591 (6) Å

  • [beta] = 93.414 (2)°

  • V = 3801.25 (14) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.72 mm-1

  • T = 100 K

  • 0.47 × 0.28 × 0.17 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.705, Tmax = 1.000

  • 14591 measured reflections

  • 7666 independent reflections

  • 7051 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.140

  • S = 1.06

  • 7666 reflections

  • 541 parameters

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

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1W 0.84 (3) 1.86 (3) 2.699 (2) 174 (3)
N2-H2N...O2W 0.98 (3) 1.69 (3) 2.661 (3) 173 (3)
O1W-H1W1...O1Bi 0.84 (3) 1.86 (3) 2.685 (2) 167 (3)
O1W-H1W1...O3Ci 0.84 (3) 2.07 (3) 2.826 (9) 149 (3)
O1W-H1W2...O3A 0.91 (4) 1.85 (4) 2.747 (2) 168 (4)
O2W-H2W1...O2Aii 0.86 (4) 1.88 (4) 2.739 (3) 176 (3)
O2W-H2W2...O1C 0.83 (5) 1.59 (5) 2.336 (10) 147 (4)
O2W-H2W2...O1B 0.83 (5) 2.01 (5) 2.830 (3) 169 (4)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, 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: LH5578 ).


Acknowledgements

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

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, 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.  [CSD] [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]
Smith, G., Bott, R. C. & Wermuth, U. D. (2001). Acta Cryst. E57, o640-o642.  [CSD] [CrossRef] [details]
Song, Y., Chidan Kumar, C. S., Nethravathi, G. B., Naveen, S. & Li, H. (2012). Acta Cryst. E68, o1747.  [CSD] [CrossRef] [details]
Towse, G. (1980). J. Laryngol. Otol. 94, 1009-1015.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o485-o486   [ doi:10.1107/S1600536813003991 ]

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