1,1′-Dimeth-oxy-3,3′-dimethyl-3,3′-(hexane-1,6-di-yl) bis(triazen-2-ium-2-olate): A nitric oxide donor

Abstract

The title compound, C10H24N6O4, is the most stable type of nitric oxide (NO) donor among the broad category of discrete N-diazeniumdiolates (NO adducts of nucleophilic small mol-ecule amines). Sitting astride a crystallographic inversion center, the mol-ecule contains a symmetric dimethyl-hexane-1,6-diamine structure bearing two planar O 2-methyl-ated N-di-azeniumdiolate functional groups [N(O)=NOMe]. These two groups are parallel to each other and have the potential to release four mol-ecules of NO. The methyl-ated diazenium-diolate substituent removes the negative charge from the typical N(O)=NO- group, thereby increasing the stability of the diazeniumdiolate structure. The crystal was nonmerohedrally twinned by a 180° rotation about the real [101] axis. This is the first N-based bis-diazeniumdiolate compound with a flexible aliphatic main unit to have its structure analyzed and this work demonstrates the utility of stabilizing the N-dia-zeniumdiolate functional group by methyl - ation. © 2009 International Union of Crystallography.