Building organic assemblies with 2-pyridone and dicarboxylic acids: Relating molecular conformation and synthon stability to crystal structure

The syntheses and crystal structures of five cocrystals; 2-pyridone oxalic acid (2/1), 2-pyridone succinic acid (2/1), 2-pyridone adipic acid (2/1) di hydrate, 2-pyridone suberic acid (2/1), and 2-pyridone sebacic acid (2/1), are reported. The competition between two similar self-complementary hydrog en-bonded synthons (carboxylic acid and 2-pyridone) are examined systematic ally in this series of cocrystals. In each case, the crystal structure cont ains planar dimers of 2-pyridone which are bridged by a dicarboxylic acid v ia a combination of C-H ... O and O-H ... O hydrogen bonds to generate infi nite 1-D ribbons. The orientation of these ribbons is determined by changes in molecular shape and conformational flexibility of the dicarboxylic acid . (C) 1999 Elsevier Science Ltd.