N-(2-Chloro-5-methyl-phen-yl)succinamic acid

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is fundamental to predicting their chemical behavior.
• Intermolecular forces, such as hydrogen bonding, play a critical role in determining the solid-state structure and properties of compounds.

Purpose of the Study:

• To elucidate the detailed molecular conformation and crystal structure of the title compound, C(11)H(12)ClNO(3).
• To investigate the role of hydrogen bonding in the self-assembly of molecules in the solid state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of bond lengths, bond angles, dihedral angles, and intermolecular interactions (hydrogen bonds).

Main Results:

• The N-H bond of the amide is syn to the ortho-Cl atom, and the amide and carboxyl C=O groups are syn.
• The dihedral angle between the benzene ring and the amide group is 47.8°.
• Molecules form inversion dimers via O-H⋯O hydrogen bonds, which are further linked into double chains by N-H⋯O hydrogen bonds along the b-axis.

Conclusions:

• The study provides a precise description of the molecular geometry and solid-state architecture of the compound.
• The identified hydrogen bonding network highlights the significant role of these interactions in directing crystal packing and supramolecular assembly.