Mehta, G. ; Sen, S. (2010) Modulating the preferred O-H···O hydrogen-bonding motif in a conformationally constrained environment through hydroxy-group derivatization Acta Crystallographica Section C: Crystal Structure Communications, 66 (2). o59-o63. ISSN 0108-2701
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Official URL: http://scripts.iucr.org/cgi-bin/paper?S01082701090...
Related URL: http://dx.doi.org/10.1107/S0108270109054870
Abstract
The crystal structures of three conformationally locked esters, namely the centrosymmetric tetrabenzoate of all-axial perhydronaphthalene-2,3,4a,6,7,8a-hexaol, viz. trans-4a,8a-dihydroxyperhydronaphthalene-2,3,6,7-tetrayl tetrabenzoate, C38H34O10, and the diacetate and dibenzoate of all-axial perhydronaphthalene-2,3,4a,8a-tetraol, viz. (2R∗ ,3R∗,4aS∗,8aS∗)-4a,8a-dihydroxyperhydronaphthalene-2,3-diyl diacetate, C14H22O6, and (2R∗,3R∗,4aS∗,8aS∗)-4a,8a-dihydroxyperhydronaphthalene-2,3-diyl dibenzoate, C24H26O6, have been analyzed in order to examine the preference of their supramolecular assemblies towards competing inter- and intramolecular O-HO hydrogen bonds. It was anticipated that the supramolecular assembly of the esters under study would adopt two principal hydrogen-bonding modes, namely one that employs intermolecular O-HO hydrogen bonds (mode 1) and another that sacrifices those for intramolecular O-H...O hydrogen bonds and settles for a crystal packing dictated by weak intermolecular interactions alone (mode 2). Thus, while the molecular assembly of the two crystalline diacyl derivatives conformed to a combination of hydrogen-bonding modes 1 and 2, the crystal packing in the tetrabenzoate preferred to follow mode 2 exclusively.
Item Type: | Article |
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Source: | Copyright of this article belongs to International Union of Crystallography. |
ID Code: | 29208 |
Deposited On: | 17 Dec 2010 08:24 |
Last Modified: | 08 Jun 2011 04:54 |
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