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The anhydrous salts of 2-(1H-indol-3-yl)ethanamine (tryptamine) with isomeric (2,4-di-chloro-phen-oxy)acetic acid (2,4-D) and (3,5-di-chloro-phen-oxy)acetic (3,5-D), both C10H13N2 (+)·C8H5Cl2O3 (-) [(I) and (II), respectively], have been determined and their one-dimensional hydrogen-bonded polymeric structures are described. In the crystal of (I), the aminium H atoms are involved in three separate inter-species N-H⋯O hydrogen-bonding inter-actions, two with carboxyl-ate O-atom acceptors and the third in an asymmetric three-centre bidentate carboxyl-ate O,O' chelate [graph set R 1 (2)(4)]. The indole H atom forms an N-H⋯Ocarboxyl-ate hydrogen bond, extending the chain structure along the b-axis direction. In (II), two of the three aminium H atoms are also involved in N-H⋯Ocarboxyl-ate hydrogen bonds similar to (I) but with the third, a three-centre asymmetric inter-action with carboxyl-ate and phen-oxy O atoms is found [graph set R 1 (2)(5)]. The chain polymeric extension is also along b. There are no π-π ring inter-actions in either of the structures. The aminium side-chain conformations differ significantly between the two structures, reflecting the conformational ambivalence of the tryptaminium cation, as found also in the benzoate salts.

acta crystallographica. section e, crystallographic communications

Crystal structures and hydrogen bonding in the anhydrous tryptaminium salts of the isomeric (2,4-dichlorophenoxy)acetic and (3,5-dichlorophenoxy)acetic acids