Bis(4-hydroxy-N-isopropyl-N-methyltryptammonium) fumarate: A new crystalline form of miprocin

Abstract

The title compound, bis(4-hydroxy-N-isopropyl-N-methyltryptammonium) (4-HO-MiPT) fumarate (systematic name: bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl](methyl)propan-2-ylazanium} but-2-enedioate), 2C14H21N2O+·C4H2O4 2-, has a singly protonated tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by N - H⋯O and O - H⋯O hydrogen bonds. These chains are a combination of R 4 2(20) rings, and C 2 2(15) and C 4 4(30) parallel chains along (110). They are further consolidated by N - H⋯π interactions. There are two two-component types of disorder impacting the tryptammonium fragment with a 0.753(7):0.247(7) occupancy ratio and one of the fumarate oxygen atoms with a 0.73(8):0.27(8) ratio.