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Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

7-Nitro-quinazolin-4(3H)-one.

Jian-Ping Yong, Guan-Ping Yu, Jiu-Ming Li

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This summary is machine-generated.

The crystal structure of C(8)H(5)N(3)O(3) reveals molecules forming dimers via N-H⋯O bonds. These dimers assemble into a 3D network through weaker C-H⋯O, C-H⋯N bonds, and π-π stacking interactions.

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Area of Science:

Crystal engineering
Supramolecular chemistry
Organic chemistry

Background:

Understanding intermolecular forces is crucial for designing materials with specific properties.
Hydrogen bonding and π-π stacking are key non-covalent interactions in crystal packing.
The title compound, C(8)H(5)N(3)O(3), presents an opportunity to study these interactions in a specific molecular framework.

Purpose of the Study:

To elucidate the crystal structure of C(8)H(5)N(3)O(3).
To identify and analyze the intermolecular interactions governing the crystal packing.
To understand how these interactions lead to the formation of a three-dimensional network.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular structure and arrangement.
Analysis of hydrogen bonding (N-H⋯O, C-H⋯O, C-H⋯N) was performed.
π-π stacking interactions were investigated, including centroid-centroid distances.

Main Results:

The crystal structure of C(8)H(5)N(3)O(3) was successfully determined.
Molecules self-assemble into centrosymmetric dimers through strong intermolecular N-H⋯O hydrogen bonds.
These dimers further connect via weaker C-H⋯O and C-H⋯N hydrogen bonds, along with π-π stacking (centroid-centroid distance of 3.678(3) Å), forming an extended three-dimensional network.

Conclusions:

The crystal structure is stabilized by a combination of strong and weak intermolecular interactions.
The identified hydrogen bonding patterns and π-π stacking interactions dictate the formation of a robust 3D supramolecular architecture.
This detailed structural analysis provides insights into the crystal engineering principles applicable to similar organic compounds.