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

Marwa Chaabene (1) , Abderrahim Khatyr (2) , Michael Knorr (2) , Moheddine Askri (1) , Yoann Rousselin (3) , Marek M. Kubicki (3)

1 CHPNR - Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité [Monastir]
2 UTINAM - Univers, Transport, Interfaces, Nanostructures, Atmosphère et environnement, Molécules (UMR 6213)
3 ICMUB - Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon]

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.

Mots clés: crystal structure; substituted 2-azabuta-1; 3-diene; weak hydrogen bonding; halogen bonding; pi-pi interactions; 1; 1-diphenyl-2-aza-1; 3-butadienes; 4; 4-dichloro-1; 1-diphenyl-2-azabuta-1; additions; bond

Domaines: Chimie

Marwa Chaabene, Abderrahim Khatyr, Michael Knorr, Moheddine Askri, Yoann Rousselin, et al.. Crystal structure of 4,4-dibromo-1-(3,4-dimethoxyphenyl)-2-azabuta-1,3-diene-1-carbonitrile. Acta crystallographica Section E : Crystallographic communications [2015-..], 2016, 72 (8), pp.1167 - 1170. ⟨10.1107/S2056989016011075⟩. ⟨hal-01400188⟩