Bis(4-hydroxy-N-isopropyl-N-methyltryptammonium) fumarate: a new crystalline form of miprocin
A.r. Chadeayne, Duyen N. K. Pham, James A. Golen, David R. Manke
Acta Crystallographica Section E Crystallographic Communications March 10, 2020 DOI: 10.1107/s2056989020002923 via OpenAlex
Summary
The crystal structure of the 4-HO-MiPT fumarate salt was determined. The compound consists of singly protonated tryptammonium cations and fumarate dianions. These ions form one-dimensional chains held together by N—H...O and O—H...O hydrogen bonds, which include R₄²(20) rings and C₂²(15) and C₄⁴(30) parallel chains along the (110) direction. Additional N—H...π interactions stabilize the structure. Two types of disorder affect the tryptammonium fragment (with a 0.753:0.247 occupancy ratio) and one fumarate oxygen atom (with a 0.73:0.27 ratio).
Study at a glance
| Characteristics | Crystallographic study Peer reviewed |
|---|---|
| Keywords | Protonation Isopropyl Dimethyl fumarate Hydrogen bond Medicinal chemistry |
| Citations | 12 |
| Key finding | The 4-HO-MiPT fumarate crystal structure exhibits one-dimensional hydrogen-bonded chains with two types of disorder in the tryptammonium and fumarate ions. |
Abstract
The title compound, bis(4-hydroxy- N -isopropyl- N -methyltryptammonium) (4-HO-MiPT) fumarate (systematic name: bis{[2-(4-hydroxy-1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium} but-2-enedioate), 2C 14 H 21 N 2 O + ·C 4 H 2 O 4 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.