1-(p-Carbamoylphenyl)-3,3-dimethyltriazene, an Antitumour Agent

Article abstract of DOI:10.1107/S0108270195008419

In the crystal structure of the title compound, 4-(3,3-dimethyl-1-triazeno)benzamide, C9H12N4O, (2), the N=N double bond <1.282 (8) Angstroem> is 0.030 Angstroem shorter than the N-N single bond <1.312 (8) Angstroem>, but both bonds are shorter than an isolated N-N single bond suggesting that there is double-bond character in each N-N bond, although it is unequally distributed.The molecule adopts a trans geometry around the N=N bond, but there is a significant deviation from planarity between the benzene ring and the plane of the triazene moiety.Compound (2) forms chains in the solid state in which the molecules are linked by C=O^...H-N hydrogen bonds between carbamoyl groups.These chains are cross-linked into sheets by hydrogen bonding between the second N-H moiety and triazene units in adjacent chains.