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rac-2-Methyl-3,4,5,6-tetrahydro-2H-2,6-methano-1,3-benzoxazocin-4-one
| Content Provider | Semantic Scholar |
|---|---|
| Author | Kettmann, Viktor Světlík, Jan Veizerová, Lucia |
| Copyright Year | 2010 |
| Abstract | The title compound, C(12)H(13)NO(2), represents a conformationally restricted 2-pyridone analogue of 1,4-dihydro-pyridine-type calcium antagonists and was selected for a crystal structure determination in order to explore some aspects of drug-receptor inter-action. In the mol-ecule, two stereogenic centres are of opposite chirality, whereas a racemate occurs in the crystal. It was found that the formally aminic N atom of the heterocycle is essentially sp(2)-hybridized with the lone-pair electrons partially delocalized through conjugation with the adjacent carbonyl bond. As a result, the central pyridone ring assumes an unsymmetrical half-chair conformation. The critical 4-phenyl ring is fixed in a pseudo-axial and perpendicular orientation [dihedral angle 85.8 (1)°] with respect to the pyridone ring via an oxygen bridge. In the crystal a pair of centrosymmetric N-H⋯O hydrogen bonds connect mol-ecules of opposite chirality into a dimer. The dimers are packed by hydrophobic van der Waals inter-actions. |
| Starting Page | o1402 |
| Ending Page | o1402 |
| Page Count | 1 |
| File Format | PDF HTM / HTML |
| DOI | 10.1107/S1600536810017848 |
| PubMed reference number | 21579481 |
| Journal | Medline |
| Volume Number | 66 |
| Journal | Acta crystallographica. Section E, Structure reports online |
| Alternate Webpage(s) | http://journals.iucr.org/e/issues/2010/06/00/kp2259/kp2259.pdf |
| Alternate Webpage(s) | https://doi.org/10.1107/S1600536810017848 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
