Molecular structures of 3‐[(2, 2, 3, 3‐tetrafluoropropoxy)methyl]‐ and 3‐[(2, 2, 3, 3, 3‐pentafluoropropoxy)methyl]pyridinium saccharinates. Issue 8 (6th July 2017)

• Record Type: Journal Article
• Authors: Lu, Norman; Chiang, Hsing-Fang; Wei, Rong-Jyun; Wen, Yuh-Sheng; Liu, Ling-Kang
• Is Part Of: Acta crystallographica. Volume 73:Issue 8(2017)
• Page Start: 593
• Page End: 599
• Publication Date: 2017-07-06
• Subjects: weak interaction -- hydrogen bonding -- pyridinium salt -- supramolecular interaction -- synthon -- saccharinate -- fluorinated -- crystal structure; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229617009512
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : Two saccharinate salts of pyridinium with –CH2 OCH2 CF2 CF2 H and –CH2 OCH2 CF2 CF3 meta substituents 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. Abstract : The salts 3‐[(2, 2, 3, 3‐tetrafluoropropoxy)methyl]pyridinium saccharinate, C9 H10 F4 NO + ·C7 H4 NO3 S −, (1), and 3‐[(2, 2, 3, 3, 3‐pentafluoropropoxy)methyl]pyridinium saccharinate, C9 H9 F5 NO + ·C7 H4 NO3 S −, (2), i.e. saccharinate (or 1, 1‐dioxo‐1λ 6, 2‐benzothiazol‐3‐olate) salts of pyridinium with –CH2 OCH2 CF2 CF2 H and –CH2 OCH2 CF2 CF3 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).