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Molecular structures of 3‐[(2,2,3,3‐tetrafluoropropoxy)methyl]‐ and 3‐[(2,2,3,3,3‐pentafluoropropoxy)methyl]pyridinium saccharinates
Author(s) -
Lu Norman,
Chiang Hsing-Fang,
Wei Rong-Jyun,
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/s2053229617009512
Subject(s) - pyridinium , chemistry , hydrogen bond , synthon , crystallography , pyridinium compounds , ring (chemistry) , salt (chemistry) , stereochemistry , medicinal chemistry , molecule , organic chemistry
The salts 3‐[(2,2,3,3‐tetrafluoropropoxy)methyl]pyridinium saccharinate, C 9 H 10 F 4 NO + ·C 7 H 4 NO 3 S − , (1), and 3‐[(2,2,3,3,3‐pentafluoropropoxy)methyl]pyridinium saccharinate, C 9 H 9 F 5 NO + ·C 7 H 4 NO 3 S − , (2), i.e. saccharinate (or 1,1‐dioxo‐1λ 6 ,2‐benzothiazol‐3‐olate) salts of pyridinium with –CH 2 OCH 2 CF 2 CF 2 H and –CH 2 OCH 2 CF 2 CF 3 meta substituents, respectively, were investigated crystallographically in order to compare their fluorine‐related weak interactions in the solid state. Both salts demonstrate a stable synthon formed by the pyridinium cation and the saccharinate anion, in which a seven‐membered ring reveals a double hydrogen‐bonding pattern. The twist between the pyridinium plane and the saccharinate plane in (2) is 21.26 (8)° and that in (1) is 8.03 (6)°. Both salts also show stacks of alternating cation–anion π‐interactions. The layer distances, calculated from the centroid of the saccharinate plane to the neighbouring pyridinium planes, above and below, are 3.406 (2) and 3.517 (2) Å in (1), and 3.409 (3) and 3.458 (3) Å in (2).