The 2:1 adducts of (benzoylmethylene)triphenylphosphorane with fumaric and terephthalic acids

Co-crystals of the ylide (benzoylmethylene)triphenylphosphorane (BPPY) with either fumaric acid, viz. (benzoylmethylene)triphenylphosphorane-fumaric acid (2/1), C(26)H(21)OP.0.5C(4)H(4)O(4), or terephthalic acid, viz. (benzoylmethylene)triphenylphosphorane-terephthalic acid (2/1), C(26)H(21)OP.0.5C(8)H(6)O(4), have a stoichiometric ratio of 2:1 between the ylide and the corresponding dicarboxylic acid. In both adducts, the acid component lies across a centre of inversion. In neither case is the ylide protonated by the organic acid; instead the H atoms of the non-ionized dicarboxylic acid molecules participate in the formation of strong O-H...O hydrogen bonds with the benzoyl O atom of the ylide species. These structures are the first reported examples of co-crystals containing non-protonated BPPY.