Crystal structure and DFT study of 8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline-9-carbaldehyde
نویسندگان
چکیده
In the title compound, C13H15NO2, the fused non-aromatic rings of the julolidine moiety adopt envelope conformations. The hy-droxy group forms an intra-molecular hydrogen bond to the aldehyde O atom, generating an S(6) ring motif. Weak inter-molecular C-H⋯O hydrogen bonds help to stabilize the crystal structure. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state.
منابع مشابه
8-{(E)-[(4-Chlorophenyl)imino]methyl}-1,1,7,7-tetramethyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-ol
The title Schiff base, C23H27ClN2O adopts the phenol-imine tautomeric form, with an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. Three C atoms of the heterocyclic moiety of the hexa-hydro-pyrido-quinoline unit, as well as the two methyl groups bonded to one of these C atoms, are disordered over two set of sites, with anoccupancy ratio of 0.740 (4):0.260 (4).
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The title compound, C23H29N3O, was synthesized from the condensation reaction of 8-hy-droxy-julolidine-9-carbaldehyde and N,N-diethyl-p-phenyl-enedi-amine. The hy-droxy group forms a intra-molecular hydrogen bond to the imine N atom and generates an S(6) ring motif. The conformation about the C=N bond is E, and the aromatic ring of the julolidine moiety is inclined to the benzene ring by 3.74 (...
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In the title mol-ecule, C(14)H(15)NO(3), the six-membered heterocyclic ring exhibits an envelope conformation. In the crystal, C-H⋯π inter-actions link the mol-ecules into centrosymmetric dimers, and weak inter-molecular C-H⋯O hydrogen bonds link these dimers into columns propagated along [100].
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The mol-ecule of the title compound, C11H9NO2, is essentially planar [r.m.s. deviation of the non-H atoms = 0.056 (1) Å]. In the crystal, strong O-H⋯O hydrogen bonds form zigzag chains along the b axis. The mol-ecules form stacks along the a axis due to π-π inter-actions, the shortest distance between the centroids of the benzene and pyridinone rings being 3.6146 (7) Å.
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