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The crystal structures of four azines, namely 1-3-bis(4-methoxyphenyl)-2,3-diaza-1,4-butadiene,  1 , 1,3-bis(2,3-dimethoxyphenyl)-2,3-diaza-1,4-butadiene,  2 , 1,3-bis(2-hydroxy-3-methoxyphenyl)-2,3-diaza-1,4-butadiene,  3 , and 1,3-bis(2-hydroxy-4-methoxyphenyl)-2,3-diaza-1,4-butadiene,  4 , are reported. Molecules of  3  and  4 , and both independent molecules of  2 , Mol A and Mol B, possess inversion centers. The central C=N–N=C units in each molecule is planar with an ( E , E ) conformation. The intermolecular interactions found in the four compounds are C–H···O, C–H–N, C–H---π and π---π interactions. However, there is no consistent set of intermolecular interactions for the four compounds. Compound,  1 , has a two-dimensional undulating sheet structure, generated from C–H···O and C–H···N intermolecular hydrogen bonds. The only recognized intermolecular interaction in  2  is a C–H···O hydrogen bond, which results in a zig-zag chain of alternating molecules, Mol A and Mol B. While  3  forms a puckered sheet of molecules, solely via C–H···π interactions, its isomeric compound, 4, has a more elaborate three-dimensional structure generated from a combination of C–H···O hydrogen bonds, C–H···π and π···π interactions.

zeitschrift für kristallographie - crystalline materials

Crystal structures and Hirshfeld surface analysis of four 1,4-bis(methoxyphenyl)-2,3-diazabuta-1,3-dienes: comparisons of the intermolecular interactions in related compounds