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Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

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Published on: February 15, 2016

6-Chloro-quinolin-2(1H)-one.

Chen-Guang Zhang1, Yang-Hui Luo

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 20, 2012
PubMed
Summary

This study details the crystal structure of a chloroquinoline compound, revealing significant deviation of the chlorine atom from the ring plane. Molecular interactions, including hydrogen bonds and pi-stacking, dictate its crystalline arrangement.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties.
  • Quinoline derivatives are important scaffolds in medicinal chemistry and materials science.
  • Detailed structural analysis provides insights into intermolecular forces and crystal packing.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(9)H(6)ClNO.
  • To analyze the molecular geometry, including the position of the chlorine atom relative to the quinoline ring.
  • To identify and characterize intermolecular interactions present in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of atomic coordinates and bond lengths/angles.
  • Identification of hydrogen bonds and π-π stacking interactions based on interatomic distances and geometry.

Main Results:

  • The chlorine atom exhibits a notable deviation of 0.142(1) Å from the mean plane of the quinoline ring.
  • Root-mean-square deviation of the quinoline ring atoms from the mean plane is 0.013 Å.
  • Molecules are linked into [010] C(4) chains via N-H⋯O hydrogen bonds.
  • Aromatic π-π stacking interactions were observed with a shortest centroid-to-centroid distance of 3.685(3) Å.

Conclusions:

  • The crystal structure of C(9)H(6)ClNO is characterized by a non-planar chlorine substitution on the quinoline ring.
  • Intermolecular hydrogen bonding and π-π stacking are key interactions governing the crystal packing.
  • These findings contribute to the understanding of structure-property relationships in substituted quinolines.