Aripiprazole salts. I. Aripiprazole nitrate

The crystal structure of aripiprazole nitrate (systematic name: 4-(2,3-dichloro­phen­yl)-1-{4-[(2-oxo-1,2,3,4-tetra­hydro­quino­lin-7-yl)­oxy]but­yl}piperazin-1-ium nitrate), C₂₃H₂₈Cl₂N₃O₂⁺·NO₃^- or AripH⁺·NO₃^-, is presented and the mol­ecule com­pared with the aripiprazole molecules reported so far in the literature. Bond distances and angles appear very similar, except for a slight lengthening of the C-NH distances involving the protonated N atom, and the main differences are to be found in the mol­ecular spatial arrangement (revealed by the sequence of torsion angles) and the inter­molecular inter­actions (resulting from structural elements specific to this structure, viz. the nitrate counter-ions on one hand and the extra protons on the other hand as hydrogen-bond acceptors and donors, respectively). The result is the formation of [100] strips, laterally linked by weak [pi]-[pi] and C-Cl...[pi] inter­actions, leading to a family of undulating sheets parallel to (010).

Aripiprazole salts. II. Aripiprazole perchlorate

The mol­ecular structure of aripiprazole perchlorate (systematic name: 4-(2,3-dichloro­phenyl)-1-{4-[(2-oxo-1,2,3,4-tetra­hydro­quinolin-7-yl)­oxy]­butyl}­piperazin-1-ium perchlor­ate), C₂₃H₂₈Cl₂N₃O₂⁺·ClO₄^-, does not differ substantially from the recently published structure of aripiprazole nitrate [Freire, Polla & Baggio (2012). Acta Cryst. C68, o170-o173]. Both compounds have almost identical bond distances, bond angles and torsion angles. The two different counter-ions occupy equivalent places in the two structures, giving rise to very similar first-order `packing motifs'. However, these elemental arrangements inter­act with each other in different ways in the two structures, leading to two-dimensional arrays with quite different organizations.