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 π-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 Å) aza­diene mol­ecules form one-dimensional double-wide ribbons through inter­molecular halogen bonds (C—Br⋯O and C—Br⋯Br—C), which then stack in a slipped manner through weak C—H⋯Br and π–π inter­actions to generate a three-dimensional network.

标题化合物C₁₂H₁₀Br₂N₂O₂属于平面π共轭（planar π-conjugated）的2-氮杂丁二烯分子，其既是用于后续有机转化反应的极具应用价值的起始原料，同时也是金属有机配位化学中的潜在配体。其分子结构参数符合(CH)₃位未取代的2-氮杂-1,3-丁二烯类化合物的典型特征。在晶体中，近乎平面（均方根偏差r.m.s. deviation = 0.0658 Å）的氮杂丁二烯分子通过分子间卤键（C—Br⋯O与C—Br⋯Br—C）形成一维双宽带状结构；随后该带状结构借助弱C—H⋯Br相互作用与π-π相互作用以滑移方式堆叠，最终构筑出三维网状结构。