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Updated: May 11, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
1-Dichloro-acetyl-t-3,t-5-dimethyl-r-2,c-6-diphenyl-piperidin-4-one
P Sugumar1, R Kayalvizhi, R Mini
1Centre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India.
This study details the molecular structure of a novel compound, C21H21Cl2NO2, revealing a distorted piperidine ring conformation. Intermolecular interactions in the crystal structure form layered networks.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Piperidine derivatives are common scaffolds in pharmaceuticals and natural products, making their structural characterization important.
Purpose of the Study:
- To elucidate the precise molecular and crystal structure of the title compound, C21H21Cl2NO2.
- To investigate the conformational preferences of the piperidine ring and the spatial arrangement of its substituents.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of intermolecular interactions, including hydrogen bonding (C-H⋯O and C-H⋯Cl), was performed.
Main Results:
- The piperidine ring in C21H21Cl2NO2 adopts a significantly distorted boat conformation.
- The phenyl rings at the 2- and 6-positions are oriented at distinct angles (87.9° and 70.8°) relative to the piperidine ring plane.
- The crystal packing reveals layered structures formed by C-H⋯O and C-H⋯Cl intermolecular interactions in the ab plane.
Conclusions:
- The study provides a detailed structural description of C21H21Cl2NO2, highlighting its unique conformational features.
- The observed intermolecular interactions offer insights into the solid-state behavior and potential for crystal engineering of this compound.
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