Chlorimipraminium picrate

Abstract

The title compound {systematic name: 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepinium picrate}, C19H24ClN2+·C6H2N3O7−, crystallizes with two independent cation–anion pairs in the asymmetric unit. The chlorimipraminium cation contains two benzene rings (one with a chloro substituent) fused to a V-shaped seven-membered azepine ring whose mean planes are separated by 61.1 (0) and 66.5 (8)° with a 3-(dimethylamino)propyl group extending away from the apex of this ring. In the picrate anion, the mean planes of the two o-NO2 groups in each anion are twisted by 3.7 (2)/31.9 (3) and 31.3 (1)/11.4 (0)°, respectively, with respect to the mean plane of the six-membered benzene ring. The phenolate O atoms are bent slightly away from the mean plane of the benzene ring. The mean planes of the p-NO2 groups are twisted by 6.6 (1) and 2.88°, respectively, from the mean plane of the benzene ring. The crystal packing features bifurcated N—H...(O,O) intermolecular hydrogen-bond interaction, which connects each cation–anion pair. Additional π–π ring and C—H...π weak intermolecular interactions are also observed.