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 P (1) over bar, a = 23.267(5), b = 8.848(2), c = 22.385(5) Angstrom, alpha = 67.93(3), beta = 70.18(3), gamma = 67.56(3)degrees, Z = 2. The homoconjugated anions with the [N-H ... N](-) bridges of 2.852(2)Angstrom 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 (d(N ... N) = 2.595(2) Angstrom) 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 degrees(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.