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Acta Cryst. (2012). E68, o3230
[ doi:10.1107/S1600536812043309 ]

3-Methyl-1,2,3,4,5,6,1',2',3',4'-decahydrospiro[benz[f]isoquinoline-1,2'-naphthalen]-1'-one

S. Siaka, A. T. Soldatenkov, A. V. Malkova, E. A. Sorokina and V. N. Khrustalev

Abstract: The title compound, C23H23NO, is the product of a tandem transformation of the double Mannich base bis(1-oxo-1,2,3,4-tertrahydro-2-naphthoylmethyl)amine hydrochloride in HBr solution upon heating. The tetrahydropyridine ring has a non-symmetrical half-chair conformation, whereas the cyclohexadiene and cyclohexene rings adopt non-symmetrical half-boat conformations. The dihedral angle between the planes of the terminal benzene rings is 62.85 (6)°. The N atom has a trigonal-pyramidal geometry [sum of the bond angles = 332.4 (3)°]. In the crystal, molecules form [001] chains via weak non-classical C-H...N hydrogen bonds. The chains are stacked along the b axis.


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