title: Supramolecular hydrogen-bonding patterns of co-crystals containing the active pharmaceutical ingredient (API) phloroglucinol and N-heterocycles.
abstract: The active pharmaceutical ingredient phloroglucinol (PHL) has been taken as an illustrative molecule to explore the intermolecular interactions which can be established with other molecular entities to build PHL pharmaceutical co-crystals. The crystal structures of five newly synthesized co-crystals are reported, where PHL is crystallized with N-heterocycles, namely 2-hydroxy-6-methylpyridine (1), 2,4-dimethyl-6-hydroxypyrimidine (2), 4-phenylpyridine (3), 2-hydroxypyridine (4) and 2,3,5,6-tetramethylpyrazine (5). The structural characteristics of these co-crystals, as far as the hydrogen-bonding networks and the crystalline architectures are concerned, are strongly dependent on the chemical features of the coformer molecules, as well as on their size and shape. A detailed analysis of the intermolecular interactions established in all the PHL co-crystals of known structures has allowed the recognition of some regularities in the packing modes that can be useful in the design of new supramolecular adducts forming predictable structural motifs.
authors.affiliation: Faculty of Medical Sciences, University Goce Delcev, Krste Misirkov bb, 2000 PO 201, Štip The Former Yugoslav Republic of Macedonia.
authors.forename: Aleksandar
authors.initials: A
authors.lastname: Cvetkovski
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Ferrara, via Fossato di Mortara 17-27, I-44121 Ferrara, Italy.
authors.forename: Valerio
authors.initials: V
authors.lastname: Bertolasi
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Ferrara, via Fossato di Mortara 17-27, I-44121 Ferrara, Italy.
authors.forename: Valeria
authors.initials: V
authors.lastname: Ferretti
mesh_terms: D003460:Crystallization; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D010696:Phloroglucinol / Q000737:chemistry*; D011719:Pyrazines / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D011728:Pyridones / Q000737:chemistry
chemical_list: D011719:Pyrazines; D011725:Pyridines; D011728:Pyridones; C051448:4-phenylpyridine; C017679:2-hydroxypyridine; D010696:Phloroglucinol
keywords: crystal packing; hydrogen bonding; pharmaceutical co-crystals; phloroglucinol