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Updated: Jun 5, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Ethyl 4-chloro-3-nitro-benzoate.
This study reveals a unique intra-molecular hydrogen bond in a C(9)H(8)ClNO(4) molecule, forming a planar ring structure. Crystal analysis further identified inter-molecular hydrogen bonds contributing to the overall molecular arrangement.
Area of Science:
- Crystallography
- Molecular Chemistry
- Supramolecular Chemistry
Background:
- Understanding molecular interactions and crystal packing is crucial in chemistry.
- Intra- and inter-molecular hydrogen bonds significantly influence molecular conformation and material properties.
Purpose of the Study:
- To elucidate the crystal structure and bonding characteristics of the title compound, C(9)H(8)ClNO(4).
- To investigate the role of intra-molecular and inter-molecular hydrogen bonds in the compound's structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks, including intra- and inter-molecular interactions.
Main Results:
- A key finding is the formation of a planar five-membered ring due to an intra-molecular C-H⋯O hydrogen bond.
- This ring system is nearly coplanar with an adjacent six-membered ring, with a dihedral angle of 4.40(3)°.
- Inter-molecular C-H⋯O hydrogen bonds were observed, mediating the linkage of molecules within the crystal lattice.
Conclusions:
- The intra-molecular hydrogen bond dictates a specific, nearly planar conformation of the C(9)H(8)ClNO(4) molecule.
- The observed crystal packing is stabilized by a network of inter-molecular C-H⋯O hydrogen bonds, highlighting their importance in supramolecular assembly.
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