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Hydrogen bonding in two tetracyclic indole alkaloids
A K Varma1, A Nangia, G R Desiraju
1School of Chemistry, University of Hyderabad, Hyderabad 500 046, India.
This study details the crystal structures of two related indoloquinolizine compounds. Both compounds exhibit layered structures stabilized by various hydrogen bonds, with weak interactions contributing to the overall network.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Indolo[2,3-a]quinolizine derivatives are known for their diverse biological activities.
- Understanding their solid-state structures is crucial for structure-activity relationship studies.
Purpose of the Study:
- To elucidate the crystal structures of two specific indoloquinolizine derivatives.
- To analyze the role of hydrogen bonding and weak interactions in their self-assembly.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Analysis of intermolecular interactions, including hydrogen bonds (N-H...O, C-H...O, O-H...O).
Main Results:
- 3-Acetyl-1,6,7,12b-tetrahydroindolo[2,3-a]quinolizin-2(12H)-one crystallizes with two independent molecules per asymmetric unit, forming layered structures.
- 3-Acetyl-6,7-dihydroindolo[2,3-a]quinolizin-4(12H)-one monohydrate features an ordered water molecule crucial for structure stabilization via hydrogen bonding.
- Both structures demonstrate the significant contribution of weak interactions to the overall hydrogen-bonded network.
Conclusions:
- The crystal packing in these indoloquinolizine derivatives is dictated by a combination of strong and weak hydrogen bonds.
- The presence of water molecules can significantly influence the self-assembly and stability of the crystal structure.
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