title: Three-dimensional hydrogen-bonded framework structures in flunarizinium nicotinate and flunarizinediium bis(4-toluenesulfonate) dihydrate.
abstract: 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.
authors.affiliation: University of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India.
authors.forename: Channappa N
authors.initials: CN
authors.lastname: Kavitha
authors.affiliation: University of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India.
authors.forename: Hemmige S
authors.initials: HS
authors.lastname: Yathirajan
authors.affiliation: University of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India.
authors.forename: Manpreet
authors.initials: M
authors.lastname: Kaur
authors.affiliation: Department of Chemistry, Nelson Mandela Metropolitan University, Summerstrand Campus (South), University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa.
authors.forename: Eric C
authors.initials: EC
authors.lastname: Hosten
authors.affiliation: Department of Chemistry, Nelson Mandela Metropolitan University, Summerstrand Campus (South), University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa.
authors.forename: Richard
authors.initials: R
authors.lastname: Betz
authors.affiliation: School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009525:Niacin / Q000737:chemistry*; D010879:Piperazines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
chemical_list: C000592715:1-(bis(4-fluorophenyl)methyl)-4-((2E)-3-phenylprop-2-en-1-yl)piperazine-1,4-diium bis(4-methylbenzenesulfonate) dihydrate; C000592713:1-bis((4-fluorophenyl)methyl)-4-((2E)-3-phenylprop-2-en-1-yl)piperazine; C000592714:4-bis((4-fluorophenyl)methyl)-1-((2E)-3-phenylprop-2-en-1-yl)piperazin-1-ium pyridine-3-carboxylate; D010879:Piperazines; D011725:Pyridines; D009525:Niacin
keywords: calcium-channel blocker; crystal structure; flunarizinediium salt; flunarizinium salt; hydrogen bonding; π–π stacking