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Six ammonium carboxyl­ate salts, namely cyclo­pentyl­ammonium cinnamate, C5H12N+·C9H7O2, (I), cyclo­hexyl­ammonium cinnamate, C6H14N+·C9H7O2, (II), cyclo­heptyl­ammonium cinnamate form I, C7H16N+·C9H7O2, (IIIa), and form II, (IIIb), cyclo­octylammonium cinnamate, C8H18N+·C9H7O2, (IV), and cyclo­dodecyl­ammonium cinnamate, C12H26N+·C9H7O2, (V), are reported. Salts (II)–(V) all have a 1:1 ratio of cation to anion and feature three N+—H...O hydrogen bonds forming one-dimensional hydrogen-bonded columns consisting of repeat­ing R43(10) rings, while salt (I) has a two-dimensional network made up of alternating R44(12) and R68(20) rings. Salt (III) consists of two polymorphic forms, viz. form I having Z′ = 1 and form II with Z′ = 2. The latter polymorph has disorder of the cyclo­heptane rings in the two cations, as well as whole-mol­ecule disorder of one of the cinnamate anions. A similar, but ordered, Z′ = 2 structure is seen in salt (IV).

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The title macrocyclic amino alcohol compound, C14H30N4O, is investigated as a solid-state synthon for the design of a self-assembled tubular structure. It crystallizes in a helical column constructed by stereospecific O—H...N and N—H...N inter­actions. The hydrogen-bonding inter­actions, dependent upon macrocyclic ring helicity and mol­ecular conformation, link R,R and S,S enantio­mers in a head-to-tail fashion, forming a continuous hydro­philic inner core.
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