4-Chloro-N-(2-chloro-phen-yl)benzamide
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the molecular structure of a dichloro compound, C(13)H(9)Cl(2)NO, revealing specific dihedral angles between its phenyl rings and amide plane. Molecules form columns via hydrogen bonds, distinct from its fluoro analog.
Area of Science:
- Crystallography
- Molecular structure analysis
- Organic chemistry
Background:
- Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Dichloro-substituted aromatic amides represent a class of compounds with potential applications in materials science and medicinal chemistry.
Purpose of the Study:
- To elucidate the detailed molecular structure of the title compound, C(13)H(9)Cl(2)NO, using single-crystal X-ray diffraction.
- To investigate the intermolecular interactions and crystal packing of the compound.
- To compare the structural features with related halogenated analogs.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular geometry.
- Identification of intermolecular interactions, including hydrogen bonds, was performed.
Main Results:
- The molecular structure reveals specific dihedral angles between the amide plane and the two distinct chlorophenyl rings (31.53(8)° and 36.23(8)°).
- A small dihedral angle (6.25(8)°) was observed between the two chlorophenyl rings.
- Molecules are arranged in columns along the b-axis, facilitated by intermolecular N-H⋯O hydrogen bonds and further stabilized by C-H⋯O interactions.
- The crystal structure is not isomorphous with the corresponding fluoro analog, indicating differences in packing and intermolecular forces.
Conclusions:
- The study provides a precise description of the solid-state structure of C(13)H(9)Cl(2)NO.
- Intermolecular hydrogen bonding plays a significant role in the crystal packing, leading to a columnar arrangement.
- Structural differences exist between this dichloro compound and its fluoro analog, highlighting the influence of halogen substituents on crystal engineering.
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