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The X-ray crystal structure of N-(1-octyl)-d-talonamide and a consideration of its hydrogen-bonding scheme

✍ Scribed by Christoph André; Peter Luger; Sönke Svenson; Jürgen-Hinrich Fuhrhop

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
619 KB
Volume
240
Category
Article
ISSN
0008-6215

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✦ Synopsis

The crystal structure of N-(l-octyl)-o-talonamide [space group P2,2,21, a = 914.0(2), b = 581.4(l), c =6257(l) pm] shows two independent molecules in the asymmetric unit. The oligomethylene chains of both molecules are extended. The talonic acid moieties have a gauche-bend along C-l-C-2-C-3-C-4 thereby avoiding a 1,3-syn interaction (0110) between O-2 and O-4, whereas the resulting Cl10 orientation between C-l and O-4 is tolerated. The molecular packing is a symmetric tail-to-tail bilayer sheet comparable to that of the diastereomeric gulonamide analogue, but in contrast to the head-to-tail packing in the gluconamide analogue. This experimental result is explained by the occurrence of different hydrogen-bond patterns between hydroxyl groups (i) of adjacent crystal sheets (talon-and gulon-amide derivative) or (ii) within one crystal sheet (gluconamide derivative).

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