2-Chloro-N-(4-meth-oxy-phen-yl)benzamide

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the solid-state structure of organic molecules is crucial for predicting their physical and chemical properties.
• Substituted benzene derivatives are common motifs in pharmaceuticals and materials science, necessitating detailed structural analysis.

Purpose of the Study:

• To elucidate the detailed three-dimensional crystal structure of the title compound, C(14)H(12)ClNO(2).
• To analyze the molecular geometry, including dihedral angles between aromatic rings and the amide group.
• To investigate intermolecular interactions, such as hydrogen bonding and C-H···π contacts, that govern crystal packing.

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 to describe the molecular conformation.
• Identification and analysis of intermolecular interactions (N-H⋯O, C-H⋯O, C-H⋯π) using crystallographic data.

Main Results:

• The chloro- and meth-oxy-substituted benzene rings exhibit a near-orthogonal arrangement (dihedral angle = 79.20(3)°).
• Significant dihedral angles were observed between the aromatic rings and the central amide unit (45.9(3)° and 33.5(3)°).
• Intermolecular N-H⋯O hydrogen bonds form C(4) chains, further stabilized by C-H⋯O and C-H⋯π interactions, creating a 3D network structure.

Conclusions:

• The crystal structure is characterized by a specific arrangement of substituted benzene rings and an amide group, dictated by steric and electronic factors.
• The identified hydrogen bonding and weaker interactions play a critical role in organizing molecules into chains and a three-dimensional supramolecular network.
• This structural information provides a foundation for understanding the compound's properties and potential applications.