3-Chloro-N,N-di­methyl­propan-1-aminium chloride

The organic cation in the title mol­ecular salt, C(5)H(13)NCl(+)·Cl(−), exhibits the gauche effect with a C—H bond of the C atom β to the chloro group donating electrons to the anti­bonding orbital of the C—Cl bond to stabilize the gauche conformation [Cl—C—C—C = −68.6 (6)°], as confirmed by DFT geometry optimizations that show a lengthening of the C—Cl bond relative to that of the anti conformation. Of further inter­est is the higher point group symmetry of the crystal ( [Image: see text] ), compared that of the that of the mol­ecular cation, which arises from a supra­molecular head-to-tail square arrangement of four mol­ecular cations that circulate in a counterclockwise direction when viewed down the tetra­gonal c axis. [Image: see text]