Ethyl 1-ethyl-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate: X-ray and DFT studies

Acta Crystallogr C. 2011 Oct;67(Pt 10):o421-4. doi: 10.1107/S0108270111038649. Epub 2011 Sep 29.

Abstract

The basic building unit in the structure of the title compound, C(14)H(14)FNO(3), is pairs of molecules arranged in an antiparallel fashion, enabling weak C-H···O interactions. Each molecule is additionally involved in π-π interactions with neighbouring molecules. The pairs of molecules formed by the C-H···O hydrogen bonds and π-π interactions form ribbon-like chains running along the c axis. Theoretical calculations based on these pairs showed that, although the main intermolecular interaction is electrostatic, it is almost completely compensated by an exchange-repulsion contribution to the total energy. As a consequence, the dominating force is a dispersion interaction. The F atoms form weak C-F···H-C interactions with the H atoms of the neighbouring ethyl groups, with H···F separations in the range 2.59-2.80 Å.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Molecular Structure
  • Quantum Theory
  • Quinolines / chemistry*

Substances

  • Quinolines
  • ethyl-1-ethyl-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate