Co-crystallization of 3,5-di-nitro-benzoic acid with two anti-psychotic 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-cyclo-hexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol (trihexyphenid-yl) with 3,5-di-nitro-benzoic acid gives a simple 1:1 salt, namely 1-(3-cyclo-hexyl-3-hy-droxy-3-phenyl-prop-yl)piperidin-1-ium 3,5-di-nitro-benzoate, C₂₀H₃₂NO⁺·C₇H₃N₂O₆ ^-, (I), whereas a similar co-crystallization using (Z)-3-(2-chloro-9H-thioxanthen-9-yl)-N,N-di-methyl-propan-1-amine (chlorprothixene) gives a 1:2 acid salt, namely (Z)-3-(2-chloro-9H-thioxanthen-9-yl)-N,N-di-methyl-propan-1-aminium hydrogen bis-(3,5-di-nitro-benzoate), C₁₈H₁₉ClNS⁺·[H(C₇H₃N₂O₆)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 cyclo-hexyl 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 ?-? stacking inter-actions 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.

SUBMITTER: Shaibah MAE 

PROVIDER: S-EPMC6362656 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature