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Abstract
One-pot synthesis of a series of four quaternary cocrystals of 3,5-dihydroxybenzoic (DHB) acid is outlined strategically based on the long-range synthon Aufbau modules (LSAM) approach exploiting hierarchical hydrogen bonding interactions. In these quaternary cocrystals, heteromeric O-H(phenolic)···N(pyridine) hydrogen bonds form a discrete closed synthon and additional heteromeric O-H(carboxylic)···N(pyridine) hydrogen bonds which lead to the formation of a one-dimensional structure. Of four quaternary cocrystals isolated, two pseudopolymorphs of DHB with tetramethylpyrazine (TMP), phenazine (PHE), and pyrene (PYR) (2:1:2:1 and 2:2:1:2 stoichiometric ratio) are observed. Both these pseudopolymorphs are composed of closed 0D tetrameric synthons consisting of two identical and distinct linker bases. Among these two, the quaternary cocrystals with stoichiometry of 2:1:2:1 are linked through DHB and PHE forming a symmetrical closed tetramer synthon, whereas quaternary cocrystals with 2:2:1:2 stoichiometric ratio are connected through DHB, TMP, and PHE forming an unsymmetrical closed tetramer synthon (anomalous synthon). ©
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