Received 18 January 2013
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: firstname.lastname@example.org
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-HOwater-HO(S)]2 hydrogen-bonded asymmetric unit is connected by further O-HO hydrogen bonds linking the components into chains along .
For cinnarizine (systematic name: 1-benzhydryl-4-cinnamyl-piperazine) as a nootropic drug, see: Towse (1980). For cinnarizine in allergic disorders, see: Barrett & Zolov (1960). For related structures, see: Bertolasi et al. (1980); Dayananda et al. (2012); Jasinski et al. (2011); Mouillé et al. (1975); Smith et al. (2001); Song et al. (2012). For puckering parameters, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5578 ).
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.
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