Cinnarizinium bis-(p-toluene-sulfonate) dihydrate

Abstract

THE ASYMMETRIC UNIT OF THE TITLE SALT [SYSTEMATIC NAME: 1-benzhydryl-4-cinnamylpiperazine-1,4-diium bis-(p-toluene-sulfonate) dihydrate], C26H30N2 (2+)·2C7H7O3S(-)·2H2O, consists of a diprotonated cinnarizinium cation hydrogen bonded through two water mol-ecules to two independent p-toluene-sulfonate 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 benzhydr-yl 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( S)]2 hydrogen-bonded asymmetric unit is connected by further O-H⋯O hydrogen bonds linking the components into chains along [100].

Fig. 1.

Molecular structure of the title compound showing 30% probability displacement ellipsoids. Dashed lines indicate N—H···O and O—H···O hydrogen bonds. One of the two independent p-toluenesulfonate anions is disordered in a 0.793 (3):0.207 (3) ratio and only the major component (B) is displayed.

Fig. 2.

Packing diagram of the title compound viewed along the c axis. Dashed lines indicate N—H···O, and O—H···O hydrogen bonds. H atoms not involved in hydrogen bonding have been removed for clarity.