Syntheses and crystal structures of three salts of 1-(4-nitrophenyl)piperazine

The crystal structures and Hirshfeld surface analyses of three salts of 1-(4-nitrophenyl)piperazine with 2-chlorobenzoic acid, 2-bromobenzoic acid and 2-iodobenzoic acid are reported. The chlorobenzoate salt, C10H14N3O2+center dot- C7H4ClO2-, contains whole-ion-disordered cations and anions, which were modeled with two equivalent conformations with occupancies of 0.745 (10)/0.255 (10) and 0.563 (13)/0.437 (13), respectively. The bromobenzoate and iodobenzoate derivatives are isomorphous and crystallize as hemihydrates, viz. C10H14N3O2+center dot C7H4BrO2-center dot 0.5H(2)O and C10H14N3O2+center dot C7H4IO2-center dot 0.5H(2)O, respectively [the water molecule is disordered over two locations with occupancies of 0.276 (3)/0.223 (3) for the iodobenzoate derivative]. In the extended structures, all three salts feature an R44(12) loop of two anions and two cations linked by N-H center dot center dot center dot O hydrogen bonds.