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Three‐dimensional hydrogen‐bonded framework structures in flunarizinium nicotinate and flunarizinediium bis(4‐toluenesulfonate) dihydrate
Author(s) -
Kavitha Channappa N.,
Yathirajan Hemmige S.,
Kaur Manpreet,
Hosten Eric C.,
Betz Richard,
Glidewell Christopher
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229614016532
Subject(s) - hydrogen bond , stacking , piperazine , crystallography , chemistry , carboxylate , pyridine , ionic bonding , stereochemistry , molecule , ion , medicinal chemistry , organic chemistry
The structures of two salts of flunarizine, namely 1‐bis[(4‐fluorophenyl)methyl]‐4‐[(2 E )‐3‐phenylprop‐2‐en‐1‐yl]piperazine, C 26 H 26 F 2 N 2 , are reported. In flunarizinium nicotinate {systematic name: 4‐bis[(4‐fluorophenyl)methyl]‐1‐[(2 E )‐3‐phenylprop‐2‐en‐1‐yl]piperazin‐1‐ium pyridine‐3‐carboxylate}, C 26 H 27 F 2 N 2 + ·C 6 H 4 NO 2 − , (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‐[(2 E )‐3‐phenylprop‐2‐en‐1‐yl]piperazine‐1,4‐diium bis(4‐methylbenzenesulfonate) dihydrate}, C 26 H 28 F 2 N 2 2+ ·2C 7 H 7 O 3 S − ·2H 2 O, (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.