A network of hydrogen bonds in the polyanion of 2-amino-4,5-dicyanoimidazole formed in the 2:1 adduct with 1,8-bis(dimethylamino)naphthalene

Crystals of the 2:1 adducts of 2-amino-4,5-dicyanoimidazole (ADCI) with 1,8-bis(dimethylamino)naphthalene (DMAN) have been grown. The triclinic lattice is formed with the space group P1̄, a = 23.267(5), b = 8.848(2), c = 22.385(5) Å, α = 67.93(3), β = 70.18(3), gg = 67.56(3)°, Z = 2. The homoconjugated anions with the [NH…N]− bridges of 2.852(2) Å are linked by additional hydrogen bonds formed by the NH2 group in such a way that polyanions of a puckered tape type are created. The two tapes are attached to each other with an opposite orientation of asymmetrical [NH…N]− bridges. The DMAN·H+ cations with asymmetrical [NH…N]+ bridges (dN…N = 2.595(2) Å) form pairs with an opposite orientation of cationic groups. The DMAN·H+ cations are ordered in stacks and form with the imidazole and imidazolate planes the angles of 56.4(2) and 64.1°(2), respectively. Relatively weak [NH…N]− bridges are well reflected in IR spectra where v(NH…N)− stretching vibration band is located at about 2800 cm−1. The asymmetry of the NH2 groups causes a considerable decoupling of v(NH) vibrations.