Weak hydrogen and halogen bonding in 4-[(2,2-difluoroethoxy)methyl]pyridinium iodide and 4-[(3-chloro-2,2,3,3-tetrafluoropropoxy)methyl]pyridinium iodide.

Author(s) Lu, N.; Wei, R.Jyun; Chiang, H.Fang; Thrasher, J.S.; Wen, Y.Sheng; Liu, L.Kang
Journal Acta Crystallogr C Struct Chem
Date Published 2017 Sep 01
Abstract

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, C8H10F2NO(+)·I(-), (1), has a -CH2OCH2CF2H substituent at the para position of the pyridinium ring and 4-[(3-chloro-2,2,3,3-tetrafluoropropoxy)methyl]pyridinium iodide, C9H9ClF4NO(+)·I(-), (2), has a -CH2OCH2CF2CF2Cl 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.

DOI 10.1107/S2053229617011172
ISSN 2053-2296
Citation Lu N, Wei RJ, Chiang HF, Thrasher JS, Wen YS, Liu LK. Weak hydrogen and halogen bonding in 4-[(2,2-difluoroethoxy)methyl]pyridinium iodide and 4-[(3-chloro-2,2,3,3-tetrafluoropropoxy)methyl]pyridinium iodide. Acta Crystallogr C Struct Chem. 2017;73(Pt 9):682-687.

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