Abstract
The enhanced influence of charge-assisted hydrogen bonds upon the resulting crystal structure in the presence of competing noncovalent interactions has been examined using single-crystal X-ray diffraction. The crystal structures of six organic salts are presented: 4-chlorobenzylammonium 2,4-dichlorobenzoate, 3-chlorobenzylammonium 2,4-dichlorobenzoate, 4-methylbenzylammonium pentafluorobenzoate, 4-chlorobenzylammonium pentafluorobenzoate, 3-methylbenzylammonium benzoate, and 4-chlorobenzylammonium benzoate monohydrate. All structures are dominated by charge-assisted \( - {\text{NH}}_{\text{3}}^{\text{ + }} \cdot \cdot \cdot ^ - {\text{OOC}} -\)hydrogen bonds that generate either one-dimensional ribbons or two-dimensional sheets. The structural influence of weaker intermolecular interactions is limited as there are very few short, halogen-halogen, π-π, or \({\text{C}} - {\text{H}} \cdot \cdot \cdot {\text{X}}\) distances in this series of compounds.
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REFERENCES
Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989. (b) Desiraju, G. R. Angew. Chem. Int. Ed. Engl. 1995, 34, 2311.
Gavezzotti, A. Acc. Chem. Res. 1994, 27, 309.
Aakeröy, C. B. Acta Crystallogr. Sect. B., 1997, 53, 569. (b) Zaworotko, M. J. Nature 1997, 386, 220.
Braga, D.; Grepioni, F.; Desiraju, G. R. Chem. Rev. 1998, 98, 1375.
Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc. Perkin Trans. 2, 1994, 2353-2360.
Price, S. L.; Stone, A. J.; Lucas, J.; Rowland, R. S.; Thornley, A. J. Am. Chem. Soc. 1994, 116, 4910. (b) Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. A. J. Am. Chem. Soc. 1996, 118, 3108.
Dunitz, J. D.; Taylor, R. Chemistry—A European J. 1997, 3, 89.
Nyburg, S. C.; Wong-Ng, W. Proc. R. Soc. London. Ser. A 1971, 367, 29.
Braga, D.; Angeloni, A.; Grepioni, F. J. Chem. Soc., Dalton Trans. 1998, 1961.
Sheldrick, G. M. SHELXL-93, University of Göttingen.
Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. Sect. B 1990, 46, 256.
Allen, F. H.; Kennard, O. Chem. Design Automation News 1993, 8, 1 and 31–37.
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Aakeröy, C.B., Beatty, A.M. & Lorimer, K.R. Charge-Assisted Hydrogen Bonds and Halogen-Halogen Interactions in Organic Salts: Benzylammonium Benzoates and Pentafluorobenzoates. Structural Chemistry 10, 229–242 (1999). https://doi.org/10.1023/A:1021892631355
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DOI: https://doi.org/10.1023/A:1021892631355