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

Acta Crystallographica Section E: Crystallographic Communications

Lynch, D.E.¹  Smith, G.² 

[1] Exilica Ltd., The Technocentre, Puma Way, Coventry CV1 2TT, England;Science and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia

关键词: CRYSTAL STRUCTURE;    TRYPTAMINE SALTS;    PHENOXYACETIC ACIDS;    HERBICIDES;    2,4-D;    3,5-D;    HYDROGEN BONDING;   

DOI  :  10.1107/S205698901500907X

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

The anhydrous salts of 2-(1H-indol-3-yl)ethanamine (tryptamine) with isomeric (2,4-di­chloro­phen­oxy)acetic acid (2,4-D) and (3,5-di­chloro­phen­oxy)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 inter­actions, two with carboxyl­ate O-atom acceptors and the third in an asymmetric three-centre bidentate carboxyl­ate O,O′ chelate [graph set R12(4)]. The indole H atom forms an N—H⋯Ocarboxyl­ate 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⋯Ocarboxyl­ate hydrogen bonds similar to (I) but with the third, a three-centre asymmetric inter­action with carboxyl­ate and phen­oxy O atoms is found [graph set R12(5)]. The chain polymeric extension is also along b. There are no π–π ring inter­actions 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.

【 授权许可】

CC BY