N-(2,4,6-Trichloro-phen-yl)maleamic acid

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Understanding molecular conformations and intermolecular interactions is crucial in crystal engineering.
• The specific arrangement of functional groups dictates crystal packing and properties.
• Intramolecular hydrogen bonding can significantly influence molecular conformation and stability.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(10)H(6)Cl(3)NO(3).
• To investigate the conformation of the amide bond and the relative orientation of the acid group's C=O and O-H bonds.
• To identify and characterize the hydrogen bonding networks present in the crystal.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
• Analysis of bond lengths, bond angles, and intermolecular contacts.
• Identification of hydrogen bond donors and acceptors.

Main Results:

• The crystal structure of C(10)H(6)Cl(3)NO(3) was successfully determined.
• The amide bond adopts a trans conformation.
• A rare anti-positioning of the C=O and O-H bonds of the acid group was observed, stabilized by an intramolecular O-H⋯O hydrogen bond to the amide carbonyl.
• Intermolecular N-H⋯O hydrogen bonds were identified, leading to the formation of zigzag chains along the c axis.

Conclusions:

• The molecular structure is stabilized by an intramolecular hydrogen bond, enforcing a specific conformation.
• The crystal packing is characterized by intermolecular hydrogen bonds forming one-dimensional zigzag chains.
• The findings provide insights into structure-property relationships for this class of compounds.