Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 9 (September 2013)

organic compounds

Acta Cryst. (2013). C69, 1055-1061    [ doi:10.1107/S0108270113019823 ]

A new structure of a serotonin salt: comparison and conformational analysis of all known serotonin complexes

D. Rychkov, E. V. Boldyreva and N. A. Tumanov

Abstract: Four serotonin salt structures (serotonin adipate, C10H13N2O+·C6H9O4-, is a previously unknown structure) were analysed to understand the influence of the anion on serotonin conformation. Hydrogen bonding alone favours a flat conformation, whereas additional stacking inter­actions between ions may possibly account for the nonplanar conformation. Since mol­ecular conformation, stability and biological activity are inter­related, one can consider influencing the chemical and biological properties of serotonin by selecting an appropriate counter-ion for salt formation.

Formula: C10H13N2O+·C6H9O4-

Keywords: crystal structure; serotonin adipate; conformation; hydrogen bonding; stacking inter­actions; Hirshfeld surfaces.

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[ doi:10.1107/S0108270113019823/yf3040Isup6.cml ]
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[ doi:10.1107/S0108270113019823/yf3040sup3.pdf ]
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