The crystalline forms of nine hydrochloride salts of substituted tryptamines

The crystal structures of the hydrochloride salts of nine substituted tryptamines, namely, 1-methyltryptammonium chloride, C 11 H 15 N 2 + ·Cl − , ( 1 ), 2-methyl-1-phenyltryptammonium chloride, C 17 H 19 N 2 + ·Cl − , ( 2 ), 5-methoxytryptammonium chloride, C 11 H 15 N 2 O + ·Cl − , ( 3 ), 5-bromotryptammonium chloride, C 10 H 12 BrN 2 + ·Cl − , ( 4 ), 5-chlorotryptammonium chloride, C 10 H 12 ClN 2 + ·Cl − , ( 5 ), 5-fluorotryptammonium chloride, C 10 H 12 FN 2 + ·Cl − , ( 6 ), 5-methyltryptammonium chloride, C 11 H 15 N 2 + ·Cl − , ( 7 ), 6-fluorotryptammonium chloride, C 10 H 12 FN 2 + ·Cl − , ( 8 ), and 7-methyltryptammonium chloride, C 11 H 15 N 2 + ·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 R 4 2 (8) and R 4 2 (18) rings, and C 2 1 (4) and C 2 1 (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.