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Crystal packing patterns for a range of chloroquine derivatives have been investigated. For species where the amine-bound R substituent carries atoms not capable of forming significant hydrogen bonding interactions, i.e. R ¼ methyl (1), n-propyl (2), n-butyl (3), 2-chloroethyl (4), 2-azidoethyl (5), N-H/N hydrogen bonding between the amine and pyridine groups predominate leading to supramolecular chains. In species carrying hydroxyl groups, i.e. R ¼ 2-hydroxylethyl ( 6), 1-butanol (7), and (S)-1-butanol ( 8), the N-H/N interactions are subverted by O-H/N and N-H/O hydrogen bonding that results in the formation of 2-D arrays, establishing an hierarchy of hydrogen bonding interactions in these systems. Despite the differences in hydrogen bonding, globally, the crystal packing in all structures is similar in that the N-H/N mediated supramolecular chains of (1-5) aggregate into layers usually via C-H/p, C-Cl/p and p/p interactions. These layers, as with those formed in (6-8), stack into a 3-D arrangement being consolidated via C-H/Cl and p/p or C-Cl/p interactions.

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