To enable a comparison between a C-H...X hydrogen bond and a halogen bond, the structures of two fluorous-substituted pyridinium iodide salts have been determined. 4-[(2,2-Difluoroethoxy)methyl]pyridinium iodide, CHFNO·I, (1), has a -CHOCHCFH substituent at the para position of the pyridinium ring and 4-[(3-chloro-2,2,3,3-tetrafluoropropoxy)methyl]pyridinium iodide, CHClFNO·I, (2), has a -CHOCHCFCFCl substituent at the para position of the pyridinium ring. In salt (1), the iodide anion is involved in one N-H...I and three C-H...I hydrogen bonds, which, together with C-H...F hydrogen bonds, link the cations and anions into a three-dimensional network. For salt (2), the iodide anion is involved in one N-H...I hydrogen bond, two C-H...I hydrogen bonds and one C-Cl...I halogen bond; additional C-H...F and C-F...F interactions link the cations and anions into a three-dimensional arrangement.

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http://dx.doi.org/10.1107/S2053229617011172DOI Listing

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