2-(4-Fluoro-phen-yl)-3-methyl-1H-indole
David B Cordes1, Guoxiong Hua, Alexandra M Z Slawin
1School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
Acta Crystallographica. Section E, Structure Reports Online
|August 13, 2011
Summary
The indole N-H hydrogen in C(15)H(12)FN does not form classical hydrogen bonds. Instead, it interacts with adjacent indole π systems, creating weakly interacting chains.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Classical hydrogen bonding is a fundamental interaction in molecular structure and function.
- Understanding non-classical interactions is crucial for predicting and designing molecular self-assembly.
- Indole derivatives are prevalent in biologically active molecules and materials.
Purpose of the Study:
- To investigate the intermolecular interactions of the title compound, C(15)H(12)FN.
- To characterize the crystal structure and identify non-classical bonding in fluorinated indoles.
- To elucidate the self-assembly behavior driven by indole N-H interactions.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure and packing.
- Analysis of intermolecular distances and angles to identify specific interactions.
- Computational methods may be used for further analysis of interaction energies (if applicable).
Main Results:
- The indole N-H group does not participate in classical hydrogen bonding.
- A significant interaction was observed between the indole N-H and the π-system of a neighboring indole ring.
- These interactions lead to the formation of extended chains along the [001] crystallographic direction.
Conclusions:
- The study reveals a non-classical hydrogen bonding motif involving indole N-H and π-systems.
- This interaction dictates the crystal packing and self-assembly of C(15)H(12)FN.
- Findings contribute to the understanding of supramolecular interactions in fluorinated indole compounds.
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