Synthesis, co-crystal structure and characterization of pyrazinamide with m-hydroxybenzoic acid, p-hydroxybenzoic acid and 3,4-dihydroxy benzolic acid

We here reported a series of co-crystal structure of pyrazinamide (PZA) with m-hydroxybenzoic acid (MHBA), p-hydroxybenzoic acid (PHBA) and 3,4-dihydroxy benzolic acid (3,4-DHBA) and obtained three co-crystals (co-crystal 1-3, respectively) under the same conditions. These crystal structures were characterized by single-crystal X-ray diffraction, IR spectra, thermogravimetric analyses, differential scanning calorimetry, and Raman spectrum analysis. The images of single crystal diffraction revealed that 1 was a 1:1 (PZA:MHBA) co-crystal, 2 was a 1:1 (PZA:PHBA) co-crystal, and 3 was a 1:1 (PZA:3,4-DHBA). The strong O-H center dot center dot center dot O, N-H center dot center dot center dot O hydrogen bonding interactions between PZA and hydroxyl-substituted benzoic acid primarily made the structure of co-crystals stabilized. Hirshfeld surface and fingerprint plots of the three co-crystals showed that the structures were stabilized by H center dot center dot center dot H, O-H center dot center dot center dot O, N-H center dot center dot center dot O C-H center dot center dot center dot pi, and pi center dot center dot center dot pi intermolecular interactions.