9-Chloro-2,4-dimethoxy-acridinium trifluoro-methane-sulfonate

Area of Science:

• Crystallography
• Molecular Chemistry
• Organic Chemistry

Background:

• Acridine derivatives are known for diverse biological and photophysical properties.
• Understanding the solid-state structure is crucial for predicting molecular behavior and designing new materials.
• The specific compound investigated is a derivative with potential applications in materials science.

Purpose of the Study:

• To elucidate the detailed molecular and crystal structure of the title compound, C(15)H(13)ClNO(2) (+)·CF(3)SO(3) (-).
• To analyze the spatial arrangement of functional groups, particularly the methoxy substituents relative to the acridine core.
• To identify and characterize intermolecular interactions governing the crystal packing.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
• Crystallographic analysis was used to measure bond lengths, bond angles, and dihedral angles.
• Intermolecular interactions, such as pi-pi stacking and hydrogen bonding, were identified and analyzed.

Main Results:

• The molecular structure reveals that the methoxy groups are nearly coplanar with the acridine ring system, with small dihedral angles of 0.4(2)° and 5.1(2)°.
• Multidirectional pi-pi contacts between adjacent acridine units were observed, indicating significant intermolecular electronic interactions.
• The crystal structure is characterized by a layer arrangement formed through N-H⋯O and C-H⋯O hydrogen bonds linking the cations and anions.

Conclusions:

• The determined crystal structure provides fundamental insights into the solid-state behavior of this acridine derivative.
• The observed coplanarity of methoxy groups and the presence of pi-pi contacts suggest potential for electronic delocalization and specific material properties.
• The hydrogen bonding network dictates the formation of a stable layer structure, relevant for crystal engineering and material design.