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

Kavitha, C. N. and Yathirajan, H. S. and Kaur, Manpreet and Hosten, Eric C. and Betz, Richard and Glidewell, Christopher (2014) Three-dimensional hydrogen-bonded framework structures in flunarizinium nicotinate and flunarizinediium bis­­(4-toluene­sulfonate) dihydrate. Acta Crystallographica Section C, 70 (8). pp. 805-811. ISSN 2053-2296

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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}, C26H28F2N22+·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.

Item Type:	Article
Uncontrolled Keywords:	crystal structure, flunarizinediium salt, flunarizinium salt, hydrogen bonding, pi-pi stacking, calcium-channel blocker
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	C Swapna Library Assistant
Date Deposited:	11 Nov 2019 05:13
Last Modified:	11 Nov 2019 05:13
URI:	http://eprints.uni-mysore.ac.in/id/eprint/9907

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