Crystal structure of 4,4-dibromo-1-(3,4-dimethoxyphenyl)-2-azabuta-1,3-diene-1-carbonitrile

The title compound, C12H10Br2N2O2, represents an example of a planar pi-conjugated 2-azabutadiene molecule, which is both an interesting starting material for further organic transformations and a potential ligand in organometallic coordination chemistry. Its metric molecular parameters are typical for the family of 2-azabuta-1,3-dienes not substituted at the (CH) 3-position. In the crystal, the almost planar (r.m.s. deviation = 0.0658 angstrom) azadiene molecules form one-dimensional double-wide ribbons through intermolecular halogen bonds (C-Br center dot center dot center dot O and C-Br center dot center dot center dot Br-C), which then stack in a slipped manner through weak C-H center dot center dot center dot Br and pi-pi interactions to generate a three-dimensional network.