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Updated: May 31, 2026
06:34
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
9-(4-Nitro-phenyl-sulfon-yl)-9H-carbazole.
Summary
This study details the crystal structure of a carbazole derivative, revealing a nearly planar skeleton. Intermolecular interactions, including hydrogen bonds and pi-pi contacts, form a stable three-dimensional network in the solid state.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Carbazole derivatives are important scaffolds in various chemical applications.
- Understanding the solid-state packing and intermolecular interactions is crucial for predicting material properties.
Purpose of the Study:
- To elucidate the crystal structure of a specific carbazole derivative (C18H12N2O4S).
- To analyze the intra- and intermolecular interactions governing its solid-state assembly.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, dihedral angles, and intermolecular contacts (hydrogen bonds, pi-pi interactions).
Main Results:
- The carbazole skeleton exhibits near planarity with a maximum deviation of 0.037 Å.
- A dihedral angle of 73.73° was observed between the carbazole and benzene rings.
- Intramolecular C-H⋯O hydrogen bonding and intermolecular C-H⋯O hydrogen bonds contribute to a 3D network. Pi-pi contacts (3.7828 Å) and C-H⋯π interactions further stabilize the structure.
Conclusions:
- The crystal structure of the title molecule is characterized by a nearly planar carbazole core and specific intermolecular interactions.
- These interactions, including hydrogen bonding and pi-pi stacking, are key to forming a stable three-dimensional supramolecular architecture.
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