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Updated: Jun 1, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one
This study details the crystal structure of a novel bromo-substituted imidazopyridine compound. The planar fused ring system and the specific twisting of its benzyl substituents were analyzed using X-ray crystallography.
Area of Science:
- Organic Chemistry
- Crystallography
- Materials Science
Background:
- Imidazopyridine derivatives are important heterocyclic compounds with diverse applications.
- Understanding the three-dimensional structure of novel derivatives is crucial for predicting their properties and reactivity.
- The synthesis and structural characterization of C(20)H(16)BrN(3)O provide insights into structure-property relationships.
Purpose of the Study:
- To determine the precise crystal structure of the title compound, C(20)H(16)BrN(3)O.
- To analyze the planarity of the imidazopyridine core and the spatial arrangement of the benzyl substituents.
- To provide foundational structural data for this specific imidazopyridine derivative.
Main Methods:
- Single crystal X-ray diffraction was employed to obtain the molecular structure.
- R.m.s. deviation calculations were used to assess the planarity of the fused ring system.
- Torsion angles were measured to quantify the twist of the phenyl rings relative to the central five-membered ring.
Main Results:
- The imidazopyridine fused-ring system in C(20)H(16)BrN(3)O was found to be planar, with an r.m.s. deviation of 0.011 Å.
- The phenyl rings of the benzyl substituents exhibit significant twisting, oriented in opposite directions.
- Specific alignment angles of 61.3(1)° and 71.2(1)° were recorded for the phenyl rings with respect to the central five-membered ring.
Conclusions:
- The structural analysis confirms the planarity of the core imidazopyridine scaffold in this compound.
- The observed twisting of benzyl substituents suggests specific packing forces or synthetic influences.
- This detailed structural information serves as a basis for further investigations into the compound's chemical and physical properties.
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