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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 Norman,
Wei Rong-Jyun,
Chiang Hsing-Fang,
Thrasher Joseph S.,
Wen Yuh-Sheng,
Liu Ling-Kang
Publication year - 2017
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229617011172
Subject(s) - pyridinium , chemistry , iodide , halogen , hydrogen bond , substituent , medicinal chemistry , pyridinium compounds , halogen bond , methyl iodide , hydrogen iodide , stereochemistry , inorganic chemistry , hydrogen , molecule , organic chemistry , alkyl
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, C 8 H 10 F 2 NO + ·I − , (1), has a –CH 2 OCH 2 CF 2 H substituent at the para position of the pyridinium ring and 4‐[(3‐chloro‐2,2,3,3‐tetrafluoropropoxy)methyl]pyridinium iodide, C 9 H 9 ClF 4 NO + ·I − , (2), has a –CH 2 OCH 2 CF 2 CF 2 Cl 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.