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Lysergol monohydrate.

Stefan Merkel¹, Robert Köppen, Matthias Koch

¹BAM Federal Institute for Materials Research and Testing, Department Analytical Chemistry, Reference Materials, Richard-Willstätter-Strasse 11, D-12489 Berlin-Adlershof, Germany.

Acta Crystallographica. Section E, Structure Reports Online

|February 21, 2012

Summary

This study details the crystal structure of lysergol monohydrate, revealing a nearly planar non-aromatic ring. Hydrogen bonding between lysergol and water molecules forms layered crystal structures.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Ergoline alkaloids, including lysergol, are a significant class of compounds with diverse biological activities.
Understanding the precise three-dimensional structure of these molecules is crucial for structure-activity relationship studies.
The crystal structure of lysergol monohydrate has not been previously detailed.

Purpose of the Study:

To elucidate the detailed crystal structure of (7-methyl-4,6,6a,7,8,9-hexa-hydro-indolo[4,3,2-fg]quinoline-9-yl)methanol monohydrate (lysergol monohydrate).
To analyze the conformation of the non-aromatic ring within the ergoline skeleton.
To investigate intermolecular interactions, specifically hydrogen bonding, in the crystalline state.

Main Methods:

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Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.

The deviation from planarity of the non-aromatic ring (ring C) was quantified.

Hydrogen bonding networks and their influence on crystal packing were examined.

Main Results:

The non-aromatic ring (ring C) of the ergoline skeleton in lysergol monohydrate is nearly planar, exhibiting a maximum deviation of 0.659(3) Å.
The non-aromatic ring adopts an envelope conformation.
Hydrogen bonds between lysergol and water molecules facilitate the formation of layered structures parallel to the (10-bar) plane.

Conclusions:

The study provides a precise structural description of lysergol monohydrate at the molecular level.
The observed near-planarity and envelope conformation of ring C offer insights into the conformational flexibility of ergoline derivatives.
The identified hydrogen bonding patterns highlight the role of water in stabilizing the crystal lattice of lysergol.