1,4-Di-[2-phenyl-1-diazenyl]perhydro-1,4-diazepine: X-ray crystal structure

Abstract

1,4-Di-[2-phenyl-1-diazenyl]perhydro-1,4-diazepine (1) has been synthesized by reaction of benzenediazonium chloride with homopiperazine (perhydro-1,4-diazepine). The crystal structure of 1 has been determined by single crystal X-ray diffraction analysis. The bis-triazene (1) adopts an extended conformation which precludes any close intramolecular interaction of the phenyl rings. The heterocyclic seven-membered ring adopts a chair conformation, with the triazene side chains occupying alternate axial and equatorial positions consistent with cis-geometry. Internal torsion angles of the seven-membered ring have been measured. The crystal packing is determined by short contacts between C=H groups of phenyl rings and nitrogens of triazene moieties and by van der Waal’s interactions, with no evidence for intermolecular π–π interactions. This work establishes the structure of the product of diazonium coupling with homopiperazine as 1,4-di[(E)-2-phenyl-1-diazenyl]perhydro-1,4-diazepine. Crystal data: 1 C17H20N6, monoclinic, space group P21/n, a = 9.1838(5) A, b = 12.1095(6) A, c = 15.0081(8) A, β = 101.320(2)∘, V = 1636.6(2) A,3 for Z = 4.