Synthesis and X-ray Studies of Novel Azaphenanthrenes

Two azaphenanthrenes were synthesised by a facile synthetic pathway and characterised by X-ray crystallography. Molecular packing of 4-(2,4-dichlorophenyl)-2-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile exhibits C–H…N and C–H…Cl hydrogen bonds in addition to intermolecular C–H…π, Cl…π and π…π...

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Bibliographic Details
Published in:Journal of chemical research 2018-02, Vol.42 (2), p.90-95
Main Authors: Girgis, Adel S., Aziz, Marian N., Shalaby, ElSayed M., Asaad, Fahmy M., Farag, I.S. Ahmed
Format: Article
Language:English
Subjects:
Chemical bonds
Chemical synthesis
Crystal structure
Crystallography
Density functional theory
Hydrogen bonds
Quinoline
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Summary:Two azaphenanthrenes were synthesised by a facile synthetic pathway and characterised by X-ray crystallography. Molecular packing of 4-(2,4-dichlorophenyl)-2-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile exhibits C–H…N and C–H…Cl hydrogen bonds in addition to intermolecular C–H…π, Cl…π and π…π (π-ring) stacking interactions. However, molecules of the 2-ethoxy derivative are linked into chains by one hydrogen bond of the C–H…N type and the crystal structure reveals an intermolecular C–H…π (π-ring) interaction. Computational studies by AM1, PM3, and density functional theory (DFT) techniques provide good approximations to the experimental X-ray data. The root mean square errors between the experimental and calculated bond lengths using AM1, PM3 and DFT methods for the 2-methoxy and 2-ethoxy derivatives are 0.0187, 0.0193, 0.0120 and 0.0197, 0.0195 and 0.0116 respectively.
ISSN:1747-5198
2047-6507
DOI:10.3184/174751918X15183538282993