1,1′-Dimeth­oxy-3,3′-dimethyl-3,3′-(hexane-1,6-di­yl)bis(triazen-2-ium-2-olate): a nitric oxide donor

The title compound, C(10)H(24)N(6)O(4), is the most stable type of nitric oxide (NO) donor among the broad category of discrete N-diazeniumdiolates (NO adducts of nucleophilic small mol­ecule amines). Sitting astride a crystallographic inversion center, the mol­ecule contains a symmetric dimethyl­hexane-1,6-diamine structure bearing two planar O (2)-methyl­ated N-di­azeniumdiolate functional groups [N(O)=NOMe]. These two groups are parallel to each other and have the potential to release four mol­ecules of NO. The methyl­ated diazenium­diolate 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-dia­zeniumdiolate functional group by methyl­­ation.