1-(p-carbamoylphenyl)-3,3-dimethyltriazene, an antitumour agent

Abstract

In the crystal structure of the title compound, 4-(3,3-dimethyl-l-triazeno)benzamide, C[subscript 9]H[subscript I2]N[subscript 4]0, (2), the N=N double bond [1.282 (8) [Angstrom]] is 0.030 [Angstrom] shorter than the N-N single bond [1.312 (8) [Angstrom]], 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.