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4-Chloro-curcumin.

Phuong-Truc T Pham1, Mamoun M Bader2

  • 1Department of Chemistry Pennsylvania State Scranton Dunmore PA 18512 USA.

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Summary
This summary is machine-generated.

This study details the crystal structure of 4-chloro-5-hydroxy-1,7-bis-(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one. The molecule exhibits a near-planar conformation with intramolecular hydrogen bonds and forms chains in the crystal lattice via intermolecular hydrogen bonds and pi-pi stacking.

Keywords:
crystal structurecurcumin derivativehydrogen bonds

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the three-dimensional structure of organic compounds is crucial for predicting their properties and reactivity.
  • Detailed structural analysis provides insights into intermolecular interactions that govern material properties.

Purpose of the Study:

  • To elucidate the crystal structure of 4-chloro-5-hydroxy-1,7-bis-(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one.
  • To investigate the molecular conformation and intermolecular interactions in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
  • Analysis of bond lengths, bond angles, dihedral angles, and hydrogen bonding networks.

Main Results:

  • The title compound, C21H19ClO6, adopts a nearly planar conformation with a dihedral angle of 2.61(7)° between the terminal phenyl groups.
  • Three intramolecular O-H⋯O hydrogen bonds were identified within the molecule.
  • In the crystal lattice, molecules are arranged into [201] chains through intermolecular O-H⋯O hydrogen bonds.
  • Weak aromatic π-π stacking interactions were observed, with the shortest centroid-centroid separation measuring 3.7279(8) Å.

Conclusions:

  • The crystal structure reveals a specific arrangement of molecules driven by hydrogen bonding and π-π stacking.
  • The near-planar geometry and identified hydrogen bonds are key features influencing the compound's solid-state packing and potential properties.