Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 10 (October 2008)

organic compounds

gd3241 scheme

Acta Cryst. (2008). C64, o561-o565 [ doi:10.1107/S0108270108028771 ]

3-Acetylanilinium bromide, nitrate and dihydrogen phosphate: hydrogen-bonding motifs in one, two and three dimensions

D. Cincic and B. Kaitner

Abstract: In the title compounds, namely 3-acetylanilinium bromide, C₈H₁₀NO⁺·Br^-, (I), 3-acetylanilinium nitrate, C₈H₁₀NO⁺·NO₃^-, (II), and 3-acetylanilinium dihydrogen phosphate, C₈H₁₀NO⁺·H₂PO₄^-, (III), each asymmetric unit contains a discrete cation, with a protonated amino group, and an anion. In the crystal structure of (I), the ions are connected via N-HBr and N-HO hydrogen bonds into a chain of spiro-fused R²₂(14) and R²₄(8) rings. In compound (II), the non-H atoms of the cation all lie on a mirror plane in the space group Pnma, while the nitrate ion lies across a mirror plane. The crystal structures of compounds (II) and (III) are characterized by hydrogen-bonded networks in two and three dimensions, respectively. The ions in (II) are connected via N-HO hydrogen bonds, with three characteristic graph-set motifs, viz. C²₂(6), R²₁(4) and R⁴₆(14). The ions in (III) are connected via N-HO and O-HO hydrogen bonds, with five characteristic graph-set motifs, viz. D, C(4), C¹₂(4), R³₃(10) and R⁴₄(12). The significance of this study lies in its illustration of the differences between the supramolecular aggregations in the bromide, nitrate and dihydrogen phosphate salts of a small organic molecule. The different geometry of the counter-ions and their different potential for hydrogen-bond formation result in markedly different hydrogen-bonding arrangements.

Formula: C₈H₁₀NO⁺·Br^-, C₈H₁₀NO⁺·NO₃^- and C₈H₁₀NO⁺·H₂O₄P^-


	Structure factor file (CIF format) (87.2 kbytes) [ doi:10.1107/S0108270108028771/gd3241Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (52.8 kbytes) [ doi:10.1107/S0108270108028771/gd3241IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (109.3 kbytes) [ doi:10.1107/S0108270108028771/gd3241IIIsup4.hkl ] Contains datablock III

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