ABSTRACT
The crystal structures of the hydrochloride salts of nine substituted tryptamines, namely, 1-methyltryptammonium chloride, C11H15N2+·Cl-, (1), 2-methyl-1-phenyltryptammonium chloride, C17H19N2+·Cl-, (2), 5-methoxytryptammonium chloride, C11H15N2O+·Cl-, (3), 5-bromotryptammonium chloride, C10H12BrN2+·Cl-, (4), 5-chlorotryptammonium chloride, C10H12ClN2+·Cl-, (5), 5-fluorotryptammonium chloride, C10H12FN2+·Cl-, (6), 5-methyltryptammonium chloride, C11H15N2+·Cl-, (7), 6-fluorotryptammonium chloride, C10H12FN2+·Cl-, (8), and 7-methyltryptammonium chloride, C11H15N2+·Cl-, (9), are reported. The seven tryptamines with N-H indoles, (3)-(9), show very similar structures, with N-H...Cl hydrogen-bonding networks forming two-dimensional sheets in the crystals. These sheets are combinations of R42(8) and R42(18) rings, and C21(4) and C21(9) chains. Substitution at the indole N atom reduces the dimensionality of the hydrogen-bonding network, with compounds (1) and (2) demonstrating one-dimensional chains that are a combination of different rings and parallel chains.
