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Co-crystals formed between anthranilic acid and each of 4,4′-bipyridine ( 1 ), 1,2-trans-1,2-bis(4-pyridyl)ethene ( 2 ) and 1,2-bis(4-pyridyl)ethane ( 3 ) have been formed from solutions containing 2:1 stoichiometric quantities of the reagents. Each structure features a centrosymmetric three-molecule aggregate mediated by O—H…N(pyridyl) hydrogen bonds indicating the robustness of the seven-membered {…HOCO…HCN} heterosynthon. The structures of ( 1 )–( 3 ) are isomorphous whereby the three-molecule aggregates are connected into flattened helical chains by amino-N—H…O(carbonyl) hydrogen bonds; the chains are consolidated into the three-dimensional structure by π…π interactions. The magnitude of the O—H…N hydrogen bonds in ( 1 )–( 3 ) are correlated with the basicity of the pyridine residue.

Persistence of the {…HOCO…HCN} heterosynthon in the co-crystals formed between anthranilic acid and three bipyridine-containing molecules