Three-dimensional hydrogen-bonded framework structures in flunarizinium nicotinate and flunarizinediium bis(4-toluenesulfonate) dihydrate.

The structures of two salts of flunarizine, namely 1-bis[(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine, C26H26F2N2, are reported. In flunarizinium nicotinate {systematic name: 4-bis[(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium pyridine-3-carboxylate}, C26H27F2N2(+)·C6H4NO2(-), (I), the two ionic components are linked by a short charge-assisted N-H...O hydrogen bond. The ion pairs are linked into a three-dimensional framework structure by three independent C-H...O hydrogen bonds, augmented by C-H...π(arene) hydrogen bonds and an aromatic π-π stacking interaction. In flunarizinediium bis(4-toluenesulfonate) dihydrate {systematic name: 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine-1,4-diium bis(4-methylbenzenesulfonate) dihydrate}, C26H28F2N2(2+)·2C7H7O3S(-)·2H2O, (II), one of the anions is disordered over two sites with occupancies of 0.832 (6) and 0.168 (6). The five independent components are linked into ribbons by two independent N-H...O hydrogen bonds and four independent O-H...O hydrogen bonds, and these ribbons are linked to form a three-dimensional framework by two independent C-H...O hydrogen bonds, but C-H...π(arene) hydrogen bonds and aromatic π-π stacking interactions are absent from the structure of (II). Comparisons are made with some related structures.