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Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions : supramolecular assembly in zero, one, two and three dimensions

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Date
11/2020
Author
Harish Chinthal, Chayanna
Kavitha, Channappa N.
Yathirajan, Hemmige S.
Foro, Sabine
Rathore, Ravindranath S.
Glidewell, Christopher
Keywords
Synthesis
Piperazines
Crystal structure
Molecular conformation
Absolute configuration
Disorder
Hydrogen bonding
Supramolecular assembly
QD Chemistry
DAS
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Abstract
Fifteen 4-(2-meth­oxy­phen­yl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. In the isostructural 4-chloro­benzoate and 4-bromo­benzoate salts, C11H17N2O+·C7H4ClO2− (I) and C11H17N2O+·C7H4BrO2− (II), and the 4-iodo­benzoate salt C11H17N2O+·C7H4IO2− (III), the ions are linked by N—H⋯O hydrogen bonds, forming centrosymmetric R44(12) four-ion aggregates; a similar aggregate is formed in the 2-chloro­benzoate salt (V), isomeric with (I). In the 2-fluoro­benzoate salt C11H17N2O+·C7H4FO2− (IV), and the isomorphous pair of salts, the 2-bromo­benzoate (VI), isomeric with (II) and 2-iodo­benzoate (VII), isomeric with (III), N—H⋯O and C—H⋯π(arene) interactions link the components into three-dimensional arrays. Four-ion R44(12) aggregates are also found in the 2-methyl­benzoate, 4-amino­benzoate and 4-nitro­benzoate salts, C11H17N2O+·C8H7O2− (VIII), C11H17N2O+·C7H6NO2− (IX) and C11H17N2O+·C7H4NO4− (X), but those in (IX) are linked into complex sheets by an additional N—H⋯O hydrogen bond. In the 3,5-dinitrobenzoate salt, C11H17N2O+·C7H3N2O6−·2H2O (XI), N—H⋯O and O—H⋯O hydrogen bonds link the components into a complex ribbon structure. In the picrate salt, C11H17N2O+·C6H2N3O7− (XII), the four-ion aggregates are linked into chains of rings by C—H⋯O hydrogen bonds. In the hydrogen maleate salt, C11H17N2O+·C4H3O4− (XIII), two- and three-centre hydrogen bonds link the ions into a ribbon structure while both anions contain very short but asymmetric O—H⋯O hydrogen bonds, having O⋯O distances of 2.4447 (16) and 2.4707 (17) Å. O—H⋯O Hydrogen bonds link the anions in the hydrogen fumarate salt (XIV), isomeric with (XIII), into chains that are linked into sheets via N—H⋯O hydrogen bonds. In the hydrogen (2R,3R)-tartrate salt, C11H17N2O+·C4H5O6−·1.698H2O (XV), the anions are linked into sheets by O—H⋯O hydrogen bonds. Comparisons are made with the structures of some related compounds.
Citation
Harish Chinthal , C , Kavitha , C N , Yathirajan , H S , Foro , S , Rathore , R S & Glidewell , C 2020 , ' Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions : supramolecular assembly in zero, one, two and three dimensions ' , Acta Crystallographica Section E , vol. 76 , no. Part 11 , pp. 1779-1793 . https://doi.org/10.1107/S2056989020014097
Publication
Acta Crystallographica Section E
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2056989020014097
ISSN
2056-9890
Type
Journal article
Rights
Copyright © 2020 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Description
HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/21013

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