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Figure 1
(a) Naftopidil (1) and coformers benzoic acid (2), 2-hy­droxy­benzoic acid, (3) 2,3-di­hydroxy­benzoic acid (4), 2,4-di­hydroxy­benzoic acid (5) and 2,6-di­hydroxy­benzoic acid (6) used for cocrystallization; and (b) the ionic synthon of the [R_2^2](9) graph set that is observed in all single-crystal structures (salts). In the synthon, complete proton transfer produces an N+—H⋯O− and O—H⋯O hydrogen-bonded cyclic motif.

IUCrJ
Volume 5| Part 6| November 2018| Pages 816-822
ISSN: 2052-2525
https://doi.org/10.1107/S2052252518014057