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1-Chloro-acetyl-2,6-bis-(2-methoxy-phen-yl)-3,5-dimethyl-piperidin-4-one.

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|May 18, 2011

Summary

This study details the molecular structure of C(23)H(26)ClNO(4), revealing a piperidone ring in a boat conformation. It also describes the perpendicular orientation of aromatic rings and observed intermolecular interactions.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure Analysis

Background:

Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
Piperidone derivatives are important scaffolds in medicinal chemistry and materials science.
Detailed structural analysis provides insights into intermolecular forces and crystal packing.

Purpose of the Study:

To elucidate the precise molecular geometry of the title compound, C(23)H(26)ClNO(4).
To investigate the conformational preferences of the piperidone ring and the spatial arrangement of its aromatic substituents.
To identify and characterize intra- and intermolecular interactions governing crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular structure.
Analysis of atomic coordinates and bond lengths/angles to define the conformation.
Geometric measurements including dihedral angles and deviations from planarity.
Identification of non-covalent interactions such as C-H⋯π and C-H⋯O.

Main Results:

The piperidone ring adopts a boat conformation, with specific deviations of carbon atoms from the ring's least-squares plane.
The two aromatic rings are oriented nearly perpendicular, with a dihedral angle of 75.1(1)°.
An intramolecular C-H⋯π interaction was observed within the molecule.
Crystal packing is stabilized by intermolecular C-H⋯O interactions, forming a chain along the a-axis.

Conclusions:

The study provides a detailed crystallographic description of C(23)H(26)ClNO(4).
The observed boat conformation and perpendicular aromatic rings highlight specific structural features.
Intermolecular C-H⋯O interactions play a significant role in the compound's crystal lattice assembly.