Disruption of a robust supramolecular heterosynthon in achiral benzylammonium and (pyridylmethyl)ammonium m-iodobenzoate salts

The X-ray crystal structures of five achiral ammonium carboxylate salts are presented: (benzylammonium)·(m-iodobenzoate) (1), ((2-pyridylmethyl) ammonium)·(m-iodobenzoate) (2), ((3-pyridylmethyl)ammonium)·(m- iodobenzoate) (3), (4-pyridylmethyl)ammonium)·(m-iodobenzoate) (4) and (4-pyridylmethyl)ammonium)·(m-iodobenzoate)·(m-iodobenzoic acid) (5). The absence of a chiral ammonium group on the cation disrupts the formation of the well-established type II robust supramolecular heterosynthon in compunds 1 and 3. All five salts have I⋯I halogen bonds and salts 1, 3 and 4 have additional C-H⋯π hydrogen bonds.