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Updated: Jun 1, 2026
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
4-Chloro-N-(2,6-dichloro-phen-yl)benzamide
Summary
This study details the crystal structure of a chlorinated amide compound, revealing varied molecular conformations and stabilization through hydrogen bonds and aromatic interactions. The findings offer insights into the solid-state behavior of such molecules.
Area of Science:
- Crystallography
- Solid-state chemistry
- Organic chemistry
Background:
- Understanding the conformational flexibility and intermolecular interactions of organic molecules in the solid state is crucial for predicting material properties.
- Amide-containing compounds are prevalent in pharmaceuticals and materials science, necessitating detailed structural analysis.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(13)H(8)Cl(3)NO.
- To analyze the molecular conformation, including dihedral angles of the amide group and aromatic rings.
- To identify and characterize the intermolecular interactions stabilizing the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
- Analysis of crystallographic data included the measurement of dihedral angles and identification of hydrogen bonds and other non-covalent interactions.
Main Results:
- The asymmetric unit contains four molecules, exhibiting a range of dihedral angles for the central amide group relative to the benzoyl and anilino rings.
- Significant twisting of the amide group out of the anilino ring plane was observed, with dihedral angles ranging from 74.3° to 88.1°.
- The crystal structure is stabilized by intermolecular N-H⋯O hydrogen bonds, π-π stacking, C-H⋯Cl hydrogen bonds, and Cl⋯Cl contacts, forming chains along the c-axis.
Conclusions:
- The study reveals considerable conformational diversity among the four molecules in the crystal lattice.
- Intermolecular interactions, including hydrogen bonding and halogen bonding (Cl⋯Cl contacts), play a vital role in the crystal packing and stability.
- The formation of an inversion dimer highlights the importance of π-π stacking and Cl⋯Cl interactions in the solid-state architecture.
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