Inter- and intramolecular C-H...π interactions in morphine bis­(1-naph­tho­ate)

The crystal structure of morphine bis­(1‐naph­tho­ate) [or 7,8‐di­de­hydro‐4,5‐epoxy‐17‐methyl­morphinan‐2,6‐diyl bis­(naph­thal­ene‐1‐carboxyl­ate)], C39H31NO5, determined at 123 K, shows extensive C—H...π interactions in the crystal lattice. Of particular interest is an intramolecular C—H...π inte...

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Bibliographic Details
Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2003-09, Vol.59 (9), p.o485-o487
Main Authors: Gathergood, Nicholas, Scammells, Peter J., Fallon, Gary D.
Format: Article
Language:English
Subjects:
Analgesics
Biological and medical sciences
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Heterocyclic compounds
Medical sciences
Neuropharmacology
Organic compounds
Pharmacology. Drug treatments
Physics
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
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Summary:The crystal structure of morphine bis­(1‐naph­tho­ate) [or 7,8‐di­de­hydro‐4,5‐epoxy‐17‐methyl­morphinan‐2,6‐diyl bis­(naph­thal­ene‐1‐carboxyl­ate)], C39H31NO5, determined at 123 K, shows extensive C—H...π interactions in the crystal lattice. Of particular interest is an intramolecular C—H...π interaction within the unit cell between the two naphthoyl groups. Comparison of the opiate scaffolds of morphine bis­(1‐naph­tho­ate) and morphine shows only a small increase in strain due to the steric bulk of the naphthoyl groups. The crystal packing shows distinct areas of packing for the naphthalene/aromatic groups and the opiate backbone. Extensive inter‐ and intramolecular C—H...π interactions lead to a densely packed aromatic region in the crystal lattice.
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270103015622