Molecular Structure Analysis of Benzamide Neuroleptics and Analogs. XII: (Exo)‐2, 3‐dimethoxy‐N‐[8]‐(Phenylmethyl)‐8 ‐AZA ‐Bicyclo [3.2.1] Oct ‐ 3 ‐ YL] Thiobenzamide, Hydrochloride

C23H28N2O2S.HCLI2 (two molecules in the asymmetric unit), Mr = 866.0, monoclinic, P21/c, a = 21.523(1), b = 13.274(1), c = 15.679(2) A, β = 94.19(1)*, V = 4467.54 A3. Z = 4, Dc = 1.29 g·cm−3, Cu Kα, λ = 1.54178 A, μ = 24.34 cm−1. F(000) = 1840, final Rw = 0.05 for 3799 observed reflections (1 ≥ 2.5 σ(1)). Bond distances and angles show a delocalization of the Π orbitals in the thioamide moiety without significant delocalization to the phenyl ring. Comparison with a very active analog, the tropepride, suggests that the decrease of the title compound antipsychotic activity is due to the lack of a strong intrabenzamidic hydrogen bond which is present in the active benzmides.