K. Jarzembska, A. Hoser, S. Varughese
Aug 8, 2017
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Journal
Crystal Growth & Design
Abstract
Four new cocrystals of pharmaceutically active N-donor compounds, pyrazinamide (P) and nicotinamide (N), with a series of dihydroxybenzoic acids, i.e., 2,3-dihydroxybenzoic acid (23DHB), 2,4-dihydroxybenzoic acid (24DHB), and 2,6-dihydroxybenzoic acid (26DHB), were synthesized and structurally evaluated in order to study basic recognition patterns and crystal lattice energetic features. The literature-reported structures of this kind, i.e., N:24DHB, N:25DHB and N:26DHB (the last two were crystallized and remeasured by us at 100 K) and P:25DHB, completed the series. The analysis of interaction networks in the examined cocrystals reflects the relative affinity of the COOH and OH groups toward N-donor compounds. A major factor that governs the primary synthon formation is the basic character of the proton acceptors in the heterocyclic compounds. In a crystal lattice, the more rigid pyrazinamide tends to form its primary structural motifs, and hence is less influenced by the molecular surrounding than nicotin...