Methyl 2-[(2-chloro-quinolin-3-yl)(hy-droxy)meth-yl]acrylate

Area of Science:

• Crystallography and Molecular Structure
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the three-dimensional arrangement of atoms in organic compounds is crucial for predicting their properties and reactivity.
• The title compound, C14H12ClNO3, presents an interesting case for structural analysis due to its functional groups and potential for varied conformations.
• Crystal structure determination provides fundamental insights into molecular geometry and intermolecular interactions.

Purpose of the Study:

• To elucidate the crystal structure of the organic compound C14H12ClNO3.
• To analyze the conformational differences between independent molecules within the asymmetric unit.
• To identify and characterize intra- and intermolecular hydrogen bonding networks.

Main Methods:

• Single-crystal X-ray diffraction was employed to collect diffraction data.
• The crystal structure was solved and refined using standard crystallographic software.
• Analysis of bond lengths, bond angles, dihedral angles, and hydrogen bonding interactions was performed.

Main Results:

• The asymmetric unit contains two independent molecules (A and B) of C14H12ClNO3.
• Significant differences in dihedral angles between the methyl ester and chloro-quilonine ring systems were observed (63.5° for A, 78.1° for B).
• Distinct torsion angles in the methyl ester unit and the presence of an intramolecular O-H⋯O hydrogen bond in molecule A were noted. Intermolecular O-H⋯(N,Cl) and C-H⋯O hydrogen bonds link molecules into chains.

Conclusions:

• The crystal structure of C14H12ClNO3 reveals conformational isomerism within the asymmetric unit.
• Intermolecular hydrogen bonding plays a significant role in the packing and assembly of molecules in the solid state.
• The detailed structural information provides a basis for understanding the chemical behavior and physical properties of this compound.