Fluorenonophane chloro-benzene solvate: mol-ecular and crystal structures

Area of Science:

• Supramolecular Chemistry
• Crystal Engineering
• Organic Chemistry

Background:

• Fluorenonophane derivatives are macrocyclic compounds with potential applications in materials science.
• Understanding the solid-state behavior of such molecules is crucial for designing new functional materials.
• Previous studies have explored the synthesis and basic properties of fluorenonophanes.

Purpose of the Study:

• To elucidate the crystal structure of a specific fluorenonophane solvate.
• To investigate the intermolecular interactions governing the crystal packing.
• To analyze the role of the chloro-benzene solvent molecule in the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Hirshfeld surface analysis was utilized to quantify and visualize intermolecular contacts.
• Two-dimensional fingerprint plots were generated to analyze the nature and distribution of these interactions.

Main Results:

• The fluorenonophane forms a solvate with chloro-benzene (C42H28O6·C6H5Cl).
• Intramolecular stacking of fluorenone units was observed due to a reduced macrocyclic cavity.
• Intermolecular interactions include weak C-H⋯π(ring) and C-H⋯Cl hydrogen bonds, with no halogen bonding involving the chlorine atom.

Conclusions:

• The crystal structure reveals a unique packing arrangement driven by π-stacking and hydrogen bonding.
• Hirshfeld surface analysis provides detailed insights into the dominance of specific intermolecular forces.
• The study contributes to the understanding of non-covalent interactions in complex organic crystal structures.