Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate

Authors : Hasan Inaç

Pages : 72-78

Doi:10.47897/bilmes.1316337

View : 128 | Download : 44

Publication Date : 2023-12-31

Article Type : Research Paper

Abstract :The title compound (1), C19H20N2O2, crystallized with single molecule in the asymmetric unit and is present in the zwitterionic form. The compound was synthesized from the condensation reaction of 8-hydroxyjulolidine-9-carbaldehyde and 3-aminophenol. In solid state compound adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N—H···O hydrogen bond with an S(6) ring motif. The conformation about the C=N bond is E. The aromatic ring of the julolidine moiety is inclined to the phenol ring by 13.00 (10)°. The fused non-aromatic rings of the julolidine moiety adopts a screw-boat conformations. In the crystal, the molecules are connected by N—H···O and O—H···O hydrogen bonds, with adjacent molecules related by a 21 screw axis, generating– A–B–A–B–zigzag chains extending along [010]. Furthermore, adjacent molecules are linked by pairs of C—H···O interactions, forming a ladder-like structure propagating along the a-axis direction. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.
Keywords : Crystal structure, schiff base, julolidine, 8 hydroxyjulolidine 9 carboxaldehyde, hydrogen bonding, zwitterion, 3 aminophenol

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