Secondary interactions in n-(chloromethyl)pyridinium chlorides (n = 2, 3, 4)

In the isomeric title compounds, viz. 2‐, 3‐ and 4‐(chloro­methyl)pyridinium chloride, C6H7ClN+·Cl−, the secondary interactions have been established as follows. Classical N—H⋯Cl− hydrogen bonds are observed in the 2‐ and 3‐isomers, whereas the 4‐isomer forms inversion‐symmetric N—H(⋯Cl−⋯)2H—N dimer...

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Bibliographic Details
Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2002-11, Vol.58 (11), p.o665-o668
Main Authors: Jones, Peter G., Vancea, Fabiola, Herbst-Irmer, Regine
Format: Article
Language:English
Subjects:
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Heterocyclic compounds
Organic compounds
Physics
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
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Summary:In the isomeric title compounds, viz. 2‐, 3‐ and 4‐(chloro­methyl)pyridinium chloride, C6H7ClN+·Cl−, the secondary interactions have been established as follows. Classical N—H⋯Cl− hydrogen bonds are observed in the 2‐ and 3‐isomers, whereas the 4‐isomer forms inversion‐symmetric N—H(⋯Cl−⋯)2H—N dimers involving three‐centre hydrogen bonds. Short Cl⋯Cl contacts are formed in both the 2‐isomer (C—Cl⋯Cl−, approximately linear at the central Cl) and the 4‐isomer (C—Cl⋯Cl—C, angles at Cl of ca 75°). Additionally, each compound displays contacts of the form C—H⋯Cl, mainly to the Cl− anion. The net effect is to create either a layer structure (3‐isomer) or a three‐dimensional packing with easily identifiable layer substructures (2‐ and 4‐isomers).
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270102017018