Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents : a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene
Abstract
Co-crystallization of racemic 1-cyclohexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol (trihexyphenidyl) with 3,5-dinitrobenzoic acid gives a simple 1:1 salt, namely 1-(3-cyclohexyl-3-hydroxy-3-phenylpropyl)piperidin-1-ium 3,5-dinitrobenzoate, C20H 32NO +·C 7H 3N 2O 6 −, (I), whereas a similar co-crystallization using (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-dimethylpropan-1-amine (chlorprothixene) gives a 1:2 acid salt, namely (Z)-3-(2-chloro-9 H-thioxanthen-9-yl)- N, N-dimethylpropan-1-aminium hydrogen bis(3,5-dinitrobenzoate), C18H 19ClNS +·[H(C 7H 3N 2O 6) 2] −, (II), the anion of which contains a very short O—H⋯O hydrogen bond, with dimensions O—H = 1.04 (3) Å, H⋯O = 1.41 (3) Å, O⋯O = 2.4197 (15) Å and O—H⋯O = 161 (3)°. In the cation of (I), the cyclohexyl and piperidyl rings both adopt chair conformations, whereas in the cation of (II), the central heterocyclic ring adopts a boat conformation, so that the dihedral angle between the two aryl rings is 41.56 (4)°. A combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions of (I) into a complex chain of rings, and these chains are linked into sheets by π– π stacking interactions between inversion-related pairs of anions. In compound (II), a different combination of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds links the ions into sheets. Comparisons are made with some related structures.
Citation
Shaibah , M A E , Yathirajan , H S , Rathore , R S , Furuya , T , Haraguchi , T , Akitsu , T & Glidewell , C 2019 , ' Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents : a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O-H···O hydrogen bond with chlorprothixene ' , Acta Crystallographica Section E , vol. 75 , no. 2 , pp. 292-298 . https://doi.org/10.1107/S2056989019001385
Publication
Acta Crystallographica Section E
Status
Peer reviewed
ISSN
2056-9890Type
Journal article
Rights
Copyright © 2019 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 is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.Collections
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