N -Cyclohexyltryptamine: freebase, bromide and fumarate

The solid-state structures of N -cyclohexyltryptamine ( I ) {systematic name: N -[2-(1 H -indol-3-yl)ethyl]cyclohexanamine}, C 16 H 22 N 2 , and two of its salts, N -cyclohexyltryptammonium bromide ( II ) {systematic name: N -[2-(1 H -indol-3-yl)ethyl]cyclohexanaminium bromide}, C 16 H 23 N 2 + ·Br...

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Bibliographic Details
Published in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2023-08, Vol.79 (8), p.752-756
Main Authors: Naeem, Marilyn, Le, Alexander N., Bauer, Barbara E., Chadeayne, Andrew R., Golen, James A., Manke, David R.
Format: Article
Language:English
Subjects:
crystal structure
hydrogen bonds
indoles
tryptamines
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Summary:The solid-state structures of N -cyclohexyltryptamine ( I ) {systematic name: N -[2-(1 H -indol-3-yl)ethyl]cyclohexanamine}, C 16 H 22 N 2 , and two of its salts, N -cyclohexyltryptammonium bromide ( II ) {systematic name: N -[2-(1 H -indol-3-yl)ethyl]cyclohexanaminium bromide}, C 16 H 23 N 2 + ·Br − , and N -cyclohexyltryptammonium fumarate ( III ) (systematic name: bis{ N -[2-(1 H -indol-3-yl)ethyl]cyclohexanaminium} (2 E )-but-2-enedioate), 2C 16 H 23 N 2 + ·C 4 H 2 O 4 2− , were determined by single-crystal X-ray diffraction. The freebase compound forms infinite chains along [010] through N—H...N hydrogen bonds. The bromide salt is held together by N—H...Br interactions in two-dimensional sheets along (001). The fumarate salt is held together in infinite three-dimensional frameworks by N—H...O hydrogen bonds.
ISSN:2056-9890
2056-9890
DOI:10.1107/S2056989023006217