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
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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.
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
Acta Crystallographica Section E
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DescriptionHSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.
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