Dimethyl and diethyl esters of 5,6-bis(pyridin-2-yl)pyrazine-2,3-dicarboxylic acid: a comparison

Abstract

In dimethyl 5,6-bis(pyridin-2-yl)pyrazine-2,3-dicarboxylate, C18H14N4O4, (I), and diethyl 5,6-bis(pyridin-2-yl)pyrazine-2,3-dicarboxylate, C20H18N4O4, (II), the dimethyl and diethyl esters of 5,6-bis(pyridin-2-yl)pyrazine-2,3-dicarboxylic acid, the orientation of the two pyridine rings differ. In (I), pyridine ringBis inclined to pyrazine ringAby 44.8 (2)° and the pyridine and pyrazine N atoms aretransto one another, while pyridine ringCis inclined to the pyrazine ring by 50.3 (2)°, with the pyridine and pyrazine N atomscisto one another. In compound (II), the diethyl ester, which possesses twofold rotation symmetry, the pyridine ring is inclined to the pyrazine ring by 40.7 (1)°, with the pyridine and pyrazine N atomstransto one another. In the crystal of (I), molecules are linked by C—H...N hydrogen bonds, forming chains along [001]. The chains are linked by C—H...π interactions, forming a three-dimensional structure. In the crystal of (II), molecules are linkedviaC—H...O hydrogen bonds, forming a three-dimensional framework. There are C—H...π interactions present within the framework.