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Inter- and intramolecular C-H...pi interactions in morphine bis(1-naphthoate)
Nicholas Gathergood1, Peter J Scammells, Gary D Fallon
1Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, Parkville, Victoria 3052, Australia. nicholas.gathergood@vcp.monash.edu.au
Summary
The crystal structure of morphine bis(1-naphthoate) reveals significant C--H...pi interactions, influencing crystal packing. These interactions create distinct regions for aromatic groups and the opiate backbone, leading to dense packing.
Area of Science:
- Crystallography
- Organic Chemistry
- Medicinal Chemistry
Background:
- Morphine derivatives are crucial in pain management.
- Understanding the structural basis of opiate activity is essential.
- Crystal structure analysis provides insights into molecular interactions.
Purpose of the Study:
- To determine the crystal structure of morphine bis(1-naphthoate).
- To investigate the role of C--H...pi interactions in its crystal lattice.
- To compare the structural strain and packing with morphine.
Main Methods:
- X-ray crystallography at 123 K.
- Analysis of intermolecular and intramolecular C--H...pi interactions.
- Comparison of opiate scaffold strain.
Main Results:
- The crystal structure of morphine bis(1-naphthoate) was determined.
- Extensive C--H...pi interactions were observed, including an intramolecular interaction between naphthoyl groups.
- Distinct packing regions for aromatic and opiate backbone components were identified.
- A small increase in strain was noted due to the naphthoyl groups' steric bulk.
Conclusions:
- C--H...pi interactions play a significant role in the crystal packing of morphine bis(1-naphthoate).
- The molecule exhibits a densely packed aromatic region due to these interactions.
- The opiate scaffold remains relatively unstrained despite the bulky substituents.