Aripiprazole salts. III. Bis(aripiprazolium) oxalate-oxalic acid (1/1).

The asymmetric unit of the title salt [systematic name: bis(4-(2,3-dichlorophenyl)-1-{4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl}piperazin-1-ium) oxalate-oxalic acid (1/1)], 2C(23)H(28)Cl(2)N(3)O(2)(+)·C(2)O(4)(2-)·C(2)H(2)O(4), consists of one protonated aripiprazole unit (HArip(+)), half an oxalate dianion and half an oxalic acid molecule, the latter two lying on inversion centres. The conformation of the HArip(+) cation differs from that in other reported salts and resembles more the conformation of neutral Arip units in reported polymorphs and solvates. The intermolecular interaction linking HArip(+) cations is also similar to those in reported Arip compounds crystallizing in the space group P1, with head-to-head N-H···O hydrogen bonds generating centrosymmetric dimers, which are further organized into planar ribbons parallel to (012). The oxalate anions and oxalic acid molecules form hydrogen-bonded chains running along [010], which 'pierce' the planar ribbons, interacting with them through a number of stronger N-H···O and weaker C-H···O hydrogen bonds, forming a three-dimensional network.