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Published on: July 30, 2017
2-Chloro-N-(3-chloro-phen-yl)benzamide
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the molecular structure of a dichloro-substituted amide, revealing specific spatial arrangements of its functional groups and rings. Molecules form chains via intermolecular hydrogen bonds, impacting crystal structure.
Area of Science:
- Crystallography and Molecular Structure
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Amide functional groups and substituted aromatic rings are common motifs in pharmaceuticals and materials science, necessitating detailed structural analysis.
Purpose of the Study:
- To elucidate the detailed crystal structure of the title compound, C(13)H(9)Cl(2)NO.
- To analyze the conformation and relative orientation of the amide group, benzoyl ring, and aniline ring.
- To investigate the intermolecular interactions governing the crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided conformational insights.
- Identification of intermolecular hydrogen bonds characterized the crystal lattice.
Main Results:
- The N-H and C=O groups of the amide moiety were found to be in a trans conformation.
- Specific syn/anti relationships were observed between the carbonyl group and the ortho-chloro substituent, and the N-H bond and the meta-chloro substituent.
- Significant dihedral angles were measured between the amide group and the aromatic rings (89.11° and 22.58°), and between the benzoyl and aniline rings (69.74°).
- Molecules were observed to form infinite chains through intermolecular N-H⋯O hydrogen bonds.
Conclusions:
- The study provides a precise structural description of C(13)H(9)Cl(2)NO, highlighting the influence of chloro-substituents on molecular conformation.
- The observed intermolecular hydrogen bonding network dictates the formation of one-dimensional supramolecular chains, a key feature of its solid-state structure.
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