Acta Crystallographica Section C
Crystal Structure Communications
Volume 64, Part 12 (December 2008)
organic compounds
The hydrogen-bonding patterns of 3-phenylpropylammonium benzoate and 3-phenylpropylammonium 3-iodobenzoate: generation of chiral crystals from achiral molecules
Abstract: The crystal structures and hydrogen-bonding patterns of 3-phenylpropylammonium benzoate, C9H14N+·C7H5O2-, (I), and 3-phenylpropylammonium 3-iodobenzoate, C9H14N+·C7H4IO2-, (II), are reported and compared. The addition of the I atom on the anion in (II) produces a different hydrogen-bonding pattern to that of (I). In addition, the supramolecular heterosynthon of (II) produces a chiral crystal packing not observed in (I). Compound (I) packs in a centrosymmetric fashion and forms achiral one-dimensional hydrogen-bonded columns through charge-assisted N-H
O hydrogen bonds. Compound (II) packs in a chiral space group and forms helical one-dimensional hydrogen-bonded columns with 21 symmetry, consisting of repeating R43(10) hydrogen-bonded rings that are commonly observed in ammonium carboxylate salts containing chiral molecules. This hydrogen-bond pattern, which has been observed repeatedly in ammonium carboxylate salts, thus provides a means of producing chiral crystal structures from achiral molecules.
Formula: C9H14N+·C7H5O2- and C9H14N+·C7H4IO2-
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