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Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-eth-oxy-quinoline-4-carboxyl-ate

Bouzian Y 1 , Karrouchi K 2 , Anouar EH 3 , Bouhfid R 4 , Arshad S 5 , Essassi EM 1

Affiliations 

  • 1 Laboratory of Heterocyclic Organic Chemistry, URAC 21, Pole of Competence, Pharmacochemistry, Av Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, Morocco
  • 2 Laboratory of Plant Chemistry, Organic and Bioorganic Synthesis, URAC23, Faculty of Science, BP 1014, GEOPAC Research Center, Mohammed V University, Rabat, Morocco
  • 3 Department of Chemistry, College of Science and Humanities, Prince Sattam Bin Abdulaziz University, PO Box 830, Al Kharj, Saudi Arabia
  • 4 Moroccan Foundation for Advanced Science, Innovation and Research (MASCIR), Rabat, Morocco
  • 5 X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Acta Crystallogr E Crystallogr Commun, 2019 Jun 01;75(Pt 6):912-916.
PMID: 31391993 DOI: 10.1107/S2056989019007473

Abstract

In the title quinoline derivative, C14H14ClNO3, there is an intra-molecular C-H⋯O hydrogen bond forming an S(6) graph-set motif. The mol-ecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-eth-oxy-quinoline mean plane. In the crystal, offset π-π inter-actions with a centroid-to-centroid distance of 3.4731 (14) Å link inversion-related mol-ecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H⋯H contacts make the largest contribution (50.8%) to the Hirshfeld surface.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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