TY - JOUR
T1 - Three cocrystals and a cocrystal salt of pyrimidin-2-amine and glutaric acid
AU - Odiase, Isaac
AU - Nicholson, Catherine E.
AU - Ahmad, Ruksanna
AU - Cooper, Jerry
AU - Yufit, Dmitry S.
AU - Cooper, Sharon J.
PY - 2015/4/1
Y1 - 2015/4/1
N2 - Four new cocrystals of pyrimidin-2-amine and propane-1,3-dicarboxylic (glutaric) acid were crystallized from three different solvents (acetonitrile, methanol and a 50:50 wt% mixture of methanol and chloroform) and their crystal structures determined. Two of the cocrystals, namely pyrimidin-2-amine-glutaric acid (1/1), C4H5N3·C6H8O4, (I) and (II), are polymorphs. The glutaric acid molecule in (I) has a linear conformation, whereas it is twisted in (II). The pyrimidin-2-amine-glutaric acid (2/1) cocrystal, 2C4H5N3·C6H8O4, (III), contains glutaric acid in its linear form. Cocrystal-salt bis(2-aminopyrimidinium) glutarate-glutaric acid (1/2), 2C4H6N3 +·C6H6O4 2-·2C6H8O4, (IV), was crystallized from the same solvent as cocrystal (II), supporting the idea of a cocrystal-salt continuum when both the neutral and ionic forms are present in appreciable concentrations in solution. The diversity of the packing motifs in (I)-(IV) is mainly caused by the conformational flexibility of glutaric acid, while the hydrogen-bond patterns show certain similarities in all four structures.
AB - Four new cocrystals of pyrimidin-2-amine and propane-1,3-dicarboxylic (glutaric) acid were crystallized from three different solvents (acetonitrile, methanol and a 50:50 wt% mixture of methanol and chloroform) and their crystal structures determined. Two of the cocrystals, namely pyrimidin-2-amine-glutaric acid (1/1), C4H5N3·C6H8O4, (I) and (II), are polymorphs. The glutaric acid molecule in (I) has a linear conformation, whereas it is twisted in (II). The pyrimidin-2-amine-glutaric acid (2/1) cocrystal, 2C4H5N3·C6H8O4, (III), contains glutaric acid in its linear form. Cocrystal-salt bis(2-aminopyrimidinium) glutarate-glutaric acid (1/2), 2C4H6N3 +·C6H6O4 2-·2C6H8O4, (IV), was crystallized from the same solvent as cocrystal (II), supporting the idea of a cocrystal-salt continuum when both the neutral and ionic forms are present in appreciable concentrations in solution. The diversity of the packing motifs in (I)-(IV) is mainly caused by the conformational flexibility of glutaric acid, while the hydrogen-bond patterns show certain similarities in all four structures.
KW - cocrystal-salt continuum
KW - cocrystals
KW - crystal engineering
KW - crystal structure
KW - glutaric acid
KW - hydrogen bonds
KW - polymorphs
KW - pyrimidin-2-amine
U2 - 10.1107/S2053229615004283
DO - 10.1107/S2053229615004283
M3 - Article
AN - SCOPUS:84926509351
VL - 71
SP - 276
EP - 283
JO - Acta crystallographica. Section C, Structural chemistry
JF - Acta crystallographica. Section C, Structural chemistry
SN - 2053-2296
IS - 4
ER -