Crystal structure and DFT study of 8-hy-droxy-1,2,3,5,6,7-hexa-hydro-pyrido[3,2,1-ij]quinoline-9-carbaldehyde.

Md Serajul Haque Faizi,Maria L Malysheva,Necmi Dege

doi:10.1107/s2056989017005886

Abstract

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.

Highlights

Julolidine is chemically an aniline derivative with two N-alkyl substituents forming rings back to the aromatic ring; the fused rings lock the nitrogen lone-pair of electrons into conjugation with the aromatic ring leading to unusual reactivity
The present work is a part of an ongoing structural study of Schiff bases based on the julolidine ring system (Faizi et al, 2016, 2017)
We report here the crystal structure and Density functional theory (DFT) computational calculation of the title julolidine compound (I)

Summary

Chemical context

Julolidine is chemically an aniline derivative with two N-alkyl substituents forming rings back to the aromatic ring; the fused rings lock the nitrogen lone-pair of electrons into conjugation with the aromatic ring leading to unusual reactivity. Julolidine malononitrile acts as a ‘push–pull’ molecule with large hyperpolarizability and is used as a model system for understanding the non-linear optical properties of molecules (Mennucci et al, 2009). Schiff bases and their applications as sensors for metal ions (Park et al, 2014; Lee et al, 2014; Kim et al, 2016). The present work is a part of an ongoing structural study of Schiff bases based on the julolidine ring system (Faizi et al, 2016, 2017). We report here the crystal structure and DFT computational calculation of the title julolidine compound (I).

Structural commentary

DFT study

Database survey

Crystallization

Refinement