Acta Crystallographica Section C

Crystal Structure Communications

Volume 62, Part 2 (February 2006)

organic compounds

hj1079 scheme

Acta Cryst. (2006). C62, o53-o57 [ doi:10.1107/S0108270105041235 ]

Three 4-aminoquinolines of antimalarial interest

S. A. Bourne, K. De Villiers and T. J. Egan

Abstract: The structures of three compounds with potential antimalarial activity are reported. In N,N-diethyl-N'-(7-iodoquinolin-4-yl)ethane-1,2-diamine, C₁₅H₂₀IN₃, (I), the molecules are linked into ribbons by N-HN and C-HN hydrogen bonds. In N-(7-bromoquinolin-4-yl)-N',N'-diethylethane-1,2-diamine dihydrate, C₁₅H₂₀BrN₃·2H₂O, (II), two aminoquinoline molecules and four water molecules form an R₅⁴(13) hydrogen-bonded ring which links to its neighbours to form a T5(2) one-dimensional infinite tape with pendant hydrogen bonds to the aminoquinolines. The phosphate salt 7-chloro-4-[2-(diethylammonio)ethylamino]quinolinium bis(dihydrogenphosphate) phosphoric acid, C₁₅H₂₂ClN₃²⁺·2H₂PO₄^-·H₃PO₄, (III), was prepared in order to establish the protonation sites of these compounds. The phosphate ions form a two-dimensional hydrogen-bonded sheet, while the aminoquinoline cations are linked to the phosphates by N-HO hydrogen bonds from each of their three N atoms. While the conformation of the quinoline region hardly varies between (I), (II) and (III), the amino side chain is much more flexible and adopts a significantly different conformation in each case. Aromatic [pi] - [pi] stacking interactions are the only supramolecular interactions seen in all three structures.

Formula: C₁₅H₂₀IN₃, C₁₅H₂₀BrN₃·2H₂O and C₁₅H₂₂ClN₃²⁺·2H₂O₄P^-·H₃O₄P


	Structure factor file (CIF format) (163.6 kbytes) [ doi:10.1107/S0108270105041235/hj1079Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (167.1 kbytes) [ doi:10.1107/S0108270105041235/hj1079IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (477.8 kbytes) [ doi:10.1107/S0108270105041235/hj1079IIIsup4.hkl ] Contains datablock III

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