Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 7 (July 2013)

organic compounds

bx2445 scheme

Acta Cryst. (2013). E69, o1131-o1132    [ doi:10.1107/S1600536813016589 ]

4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride

R. Centore and V. Piccialli

Abstract: The title compound, C8H13N10+·Cl-, is the monochlorhydrate salt of an aromatic bis(diaminotriazole). The cation is centrosymmetric, lying about an inversion centre (Ci symmetry) because the acidic H atom is disordered over two centrosymmetrically related ring N atoms, with equal multiplicity. It is noteworthy that protonation occurs at an N atom of the ring, instead of at the C-NH2 or N-NH2 amino groups. The chloride anions are also in special positions, as they lie on binary axes, and so the crystallographically independent unit contains half of a formula unit. The N atom of the C-NH2 group is sp2-hybridized and the amino group is coplanar with the triazole ring [dihedral angle = 5 (3)°], while the N atom of the N-NH2 amino group is pyramidal. The C=C bonds are in E conformations and the cation is flat because the conformation of the carbon chain is fully extended. The chloride anions are hexacoordinated, in a distorted trigonal-prismatic geometry, and they are involved, as acceptors, in six hydrogen bonds. Chains of hydrogen-bonded cations, running along c and a + c, are generated by c-glide and C2 rotation, respectively. This combination of N-H...Cl and N-H...N hydrogen bonds leads to the formation of a three-dimensional network.

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