3-Chloro-N-(2-chloro-phen-yl)benzamide

Area of Science:

• Organic Chemistry
• Crystallography
• Molecular Structure

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their chemical and physical properties.
• Substituent effects, such as halogenation, can significantly influence molecular conformation and intermolecular interactions.
• Crystal structure analysis provides definitive insights into molecular geometry and packing in the solid state.

Purpose of the Study:

• To elucidate the detailed crystal structure of a specific dichlorinated benzanilide compound (C(13)H(9)Cl(2)NO).
• To analyze the conformational preferences of the benzoyl and aniline rings.
• To identify and characterize the intermolecular interactions stabilizing the crystal lattice.

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 conformational information.
• Identification of hydrogen bonding networks and their role in crystal packing.

Main Results:

• The crystal structure reveals a meta-chlorine atom on the benzoyl ring positioned anti to the carbonyl group and an ortho-chlorine atom on the aniline ring positioned syn to the N-H bond.
• The two aromatic rings exhibit a near-coplanar arrangement, with a small dihedral angle of 4.73(5)°.
• The crystal lattice is stabilized by intermolecular N-H⋯O hydrogen bonds, forming chains along the b-axis.

Conclusions:

• The specific positioning of chlorine substituents influences the relative orientation of the aromatic rings.
• The near-planar conformation and the observed hydrogen bonding pattern are key features of this dichlorinated benzanilide's solid-state structure.
• The N-H⋯O hydrogen bonds play a critical role in directing the self-assembly of molecules into one-dimensional chains.