1-Chloro-acetyl-2,6-bis-(3-fluoro-phen-yl)piperidin-4-one

Area of Science:

• Crystallography
• Organic Chemistry
• Materials Science

Background:

• Understanding molecular conformation and crystal packing is crucial for predicting material properties.
• Piperidone derivatives are important scaffolds in medicinal chemistry and materials science.

Purpose of the Study:

• To elucidate the three-dimensional structure and intermolecular interactions of the title compound C(19)H(16)ClF(2)NO(2).
• To analyze the conformational preferences of the piperidone ring and the factors governing crystal lattice assembly.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of bond lengths, bond angles, and non-covalent interactions was performed.

Main Results:

• The piperidone ring adopts a twist-boat conformation, with significant deviations of out-of-plane atoms.
• Sterically favored non-hydrogen atom C⋯O intermolecular contacts were identified within 3.00 Å.
• Crystal packing is stabilized by C-H⋯O and C-H⋯F hydrogen bonds, alongside π-π interactions (3.783 Å separation).
• Chains along the a-axis are formed by alternating C-H⋯O and C-H⋯F interactions.
• A centrosymmetric R(2)(2)(16) ring involving C-H⋯O interactions was observed.

Conclusions:

• The study provides detailed structural insights into the C(19)H(16)ClF(2)NO(2) compound.
• The identified intermolecular interactions highlight key stabilizing forces within the crystal structure.
• The conformational analysis contributes to understanding structure-property relationships in related piperidone derivatives.