Inter- and intramolecular C-H...pi 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)], C(39)H(31)NO(5), determined at 123 K, shows extensive C--H...pi interactions in the crystal lattice. Of particular interest is an intramolecular C--H...pi 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...pi interactions lead to a densely packed aromatic region in the crystal lattice.
Gathergood
Nicholas
N
Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, Parkville, Victoria 3052, Australia. nicholas.gathergood@vcp.monash.edu.au
Scammells
Peter J
PJ
Fallon
Gary D
GD