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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
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Published on: May 27, 2014

2-Amino-5-fluoro-benzoic acid.

S Sreenivasa1, K E Manojkumar, P A Suchetan

  • 1Department of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary

The crystal structure of C7H6FNO2 reveals a nearly planar molecule with an intramolecular hydrogen bond. Intermolecular interactions, including hydrogen bonds and pi-pi stacking, further stabilize the crystal lattice.

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Area of Science:

  • Crystallography
  • Molecular structure analysis
  • Supramolecular chemistry

Background:

  • Understanding molecular interactions is crucial for materials science.
  • Crystal engineering relies on predicting and controlling intermolecular forces.
  • The title compound, C7H6FNO2, presents an interesting case for studying hydrogen bonding and packing motifs.

Purpose of the Study:

  • To elucidate the crystal structure of C7H6FNO2.
  • To identify and characterize intra- and intermolecular interactions within the crystal lattice.
  • To analyze the role of hydrogen bonding and other non-covalent interactions in crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Analysis of bond lengths, bond angles, and intermolecular distances.
  • Identification of hydrogen bonding networks and aromatic interactions.

Main Results:

  • The molecule C7H6FNO2 exhibits a nearly planar conformation with an r.m.s. deviation of 0.015 Å for non-hydrogen atoms.
  • An intramolecular N-H⋯O hydrogen bond forms a six-membered (S(6)) ring.
  • In the crystal, inversion dimers formed by O-H⋯O hydrogen bonds create R2(2)(8) loops, alongside weak N-H⋯F bonds, short F⋯F contacts (2.763 Å), and aromatic π-π stacking (3.557 Å).

Conclusions:

  • The crystal structure is stabilized by a combination of intramolecular and intermolecular hydrogen bonds.
  • Aromatic π-π stacking and short fluorine-fluorine contacts contribute to the overall crystal packing.
  • The detailed structural analysis provides insights into the intermolecular forces governing the solid-state arrangement of C7H6FNO2.