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Supramolecular structures of substituted α,α′‐trehalose derivatives
Author(s) -
Baddeley Thomas C.,
Davidson Iain G.,
Glidewell Christopher,
Low John N.,
Skakle Janet M. S.,
Wardell James L.
Publication year - 2004
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
eISSN - 1600-5740
pISSN - 0108-7681
DOI - 10.1107/s0108768104010912
Subject(s) - trehalose , molecule , hydrogen bond , chemistry , crystallography , stereochemistry , supramolecular chemistry , crystal structure , organic chemistry
The structures of five substituted α,α′‐trehalose trehalose derivatives have been determined, and these are compared with those of four previously published analogues. In 2,2′,3,3′,4,4′‐hexaacetato‐6,6′‐bis‐ O ‐methylsulfonyl‐α,α′‐trehalose, C 26 H 38 O 21 S 2 , where the molecules lie across twofold rotation axes in the space group C 2, a single C—H⋯O=S hydrogen bond links the molecules into sheets. 2,2′,3,3′,4,4′‐Hexaacetato‐6,6′‐bis‐ O ‐(4‐toluenesulfonyl)‐α,α′‐trehalose, C 38 H 46 O 21 S 2 , crystallizes with Z ′ = 2 in the space group P 2 1 2 1 2 1 and a combination of three C—H⋯O hydrogen bonds, each having a carbonyl O atom as an acceptor, and a C—H⋯π(arene) hydrogen bond link the molecules into a three‐dimensional framework. 2,2′,3,3′,4,4′‐Hexaacetato‐6,6′‐diazido‐α,α′‐trehalose, C 24 H 32 N 6 O 15 , crystallizes as a partial ethanol solvate and three C—H⋯O hydrogen bonds link the substituted trehalose molecules into a three‐dimensional framework. In 2,2′,3,3′‐tetraacetato‐6,6′‐bis( N ‐acetylamino)‐α,α′‐trehalose dihydrate, C 24 H 36 N 2 O 15 ·2H 2 O, the substituted trehalose molecules lie across twofold rotation axes in the space group P 2 1 2 1 2 and a three‐dimensional framework is generated by the combination of O—H⋯O and N—H⋯O hydrogen bonds. The diaminotrehalose molecules in 6,6′‐diamino‐α,α′‐trehalose dihydrate, C 12 H 24 N 2 O 9 .2(H 2 O), lie across twofold rotation axes in the space group P 4 3 2 1 2: a single O—H⋯N hydrogen bond links the trehalose molecules into sheets, which are linked into a three‐dimensional framework by O—H⋯O hydrogen bonds.

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