Desipramine hydrochloride: a non-merohedrally twinned structure

Abstract

The title compound, C18H23N2 +·Cl−, is a non-merohedrally twinned salt [domains 0.9288 (3) and 0.0712 (3)] which crystallizes with four independent cation–anion pairs in the asymmetric unit. The seven-membered ring in each of the cations adopts a boat conformation, thus creating a butterfly effect within the ring system. The average value of the dihedral angle between the two aromatic rings in the four cations is 57.1 (1)°. The crystal packing is stabilized only slightly by a collection of inter­mediate N—H⋯Cl hydrogen-bonding inter­actions, which produce a weak, but cooperative, infinite, one-dimensional, inter­molecular hydrogen-bond network along the a axis. A MOPAC PM3 computational calculation gives support to these observations.

Syntheses, crystal structures and Hirshfeld surface analyses of four molecular salts of amitriptynol

“…Lastly, entry YEYTUS (Portalone et al, 2007) is the free-base amitriptynol, from which salts I-IV were prepared. Other related structures, not returned in the above CSD search, include nortriptyline hydrochloride (JINGIW; Klein et al, 1991), three tricyclic neuroleptics (MEAPOT11, YOVYUD, and YOVZEO; Klein et al, 1994), amitriptylinium picrate (DIKWEA; Bindya et al, 2007), desipraminium chloride (PUKGEI; Jasinski et al, 2010), desipraminium picrate (HISHEX; Swamy et al, 2007), imipramine hydrochloride and desipramine hydrochloride (PAJTON and PALBOX; Aree, 2020b).…”