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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
6.3K
7-Chloro-3-(4-methyl-benzene-sulfon-yl)pyrrolo[1,2-c]pyrimidine
Easha Narayan1, Liangfeng Fu1, Gordon W Gribble1
1Department of Chemistry, Dartmouth College, Hanover, NH 03755 , USA.
Iucrdata
|November 7, 2022
Summary
This study details the crystal structure of a novel pyrrolo-[1,2-c]pyrimidine derivative. Molecular packing is influenced by hydrogen bonding and aromatic π-π stacking interactions, revealing key structural insights.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the solid-state structure of heterocyclic compounds is crucial for predicting their physical and chemical properties.
- Pyrrolo-[1,2-c]pyrimidine scaffolds are of interest in medicinal chemistry and materials science.
Purpose of the Study:
- To elucidate the crystal structure of a specific C14H11ClN2O2S compound.
- To analyze the intermolecular interactions governing crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of non-covalent interactions, including hydrogen bonding and π-π stacking, was performed.
Main Results:
- The dihedral angle between the pyrrolo-[1,2-c]pyrimidine system and the benzene ring is 80.2(9)°.
- Inversion dimers formed by C-H⋯O interactions and aromatic π-π stacking interactions were identified as key packing forces.
- The shortest centroid-centroid separation for π-π stacking was 3.5758(14) Å.
Conclusions:
- The crystal packing of the title compound is significantly influenced by a combination of hydrogen bonding and aromatic π-π stacking.
- These interactions lead to the formation of specific supramolecular motifs (R22(16) loops) and contribute to the overall stability of the crystal lattice.
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