Abstract
The solid-state structures of N-cyclohexyltryptamine (I) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanamine}, C16H22N2, and two of its salts, N-cyclohexyltryptammonium bromide (II) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium bromide}, C16H23N2+center dot Br-, and N-cyclohexyl-tryptammonium fumarate (III) (systematic name: bis{N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium} (2E)-but-2-enedioate), 2C(16)H(23)N(2)(+)center dot C4H2O42-, were determined by single-crystal X-ray diffraction. The freebase compound forms infinite chains along [010] through N-H center dot center dot center dot N hydrogen bonds. The bromide salt is held together by N-H center dot center dot center dot Br interactions in two-dimensional sheets along (001). The fumarate salt is held together in infinite three-dimensional frameworks by N-H center dot center dot center dot O hydrogen bonds.