Abstract
4-(E)-2-[3-(3-[(E)-2-(4-cyanophenyl)-1-diazenyl]hexahydro-1-pyrimidinylmethyl)hexahydro-1-pyrimidinyl]-1-diazenylbenzonitrile (1) has been synthesized by reaction of p-cyanobenzene diazonium chloride with a mixture of formaldehyde and 1,3-propanediamine. The crystal structure has been determined by single crystal X-ray diffraction analysis. The bis-triazene (1) adopts a folded conformation, similar to previously studied ethylenediamine analogues, and there is evidence of π-stacking in the crystal packing. The two planar phenyltriazenyl groups are almost parallel, forming an angle of 6.6(1)∘, and display weak intermolecular π ⋅s π interactions between molecules. This result establishes the structure of the product of this diazonium coupling reaction as the 1-(1-hexahydropyimidinylmethyl)hexahydropyrimidine derivative and not the alternate tetraazabicyclo[5.5.1]tridecane derivative. Crystal data: 1C23H26N10, monoclinic, space group P21/c, a = 10.717(1) A, b = 7.749(1) A, c = 28.252(2) A, β = 97.223(2)∘, V = 2327.5(5) A3, for Z = 4.
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