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Solvated and solvent-free forms of N,N'-dithiodiphthalimide
J M Skakle1, J L Wardell, J N Low
1Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland.
Summary
N,N'-Dithiodiphthalimide exhibits distinct crystal structures based on solvent. Hydrogen bonds and pi-pi stacking form 3D frameworks in ethyl acetate, while solvates in other solvents feature channels for solvent molecules.
Area of Science:
- Crystallography
- Solid-state chemistry
- Organic chemistry
Background:
- N,N '-Dithiodiphthalimide (C16H8N2O4S2) is a sulfur-containing organic compound.
- Polymorphism and solvate formation are common phenomena in organic crystalline materials.
- Understanding crystal packing influences material properties.
Purpose of the Study:
- To investigate the crystal structures of N,N '-Dithiodiphthalimide.
- To determine the impact of crystallization solvent on molecular arrangement and intermolecular interactions.
- To characterize the formation of solvates and their structural implications.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Crystallization from various organic solvents (ethyl acetate, dichloromethane, ethanol).
- Analysis of molecular conformation, hydrogen bonding, and pi-pi stacking interactions.
Main Results:
- Crystallization from ethyl acetate yielded two independent molecules in the asymmetric unit, forming a 3D framework via hydrogen bonds and pi-pi stacking.
- Crystallization from dichloromethane or ethanol resulted in solvates with molecules on twofold rotation axes (space group C2/c).
- These solvates lack hydrogen bonds but exhibit pi-pi stacking into chains with channels (approx. 20% of unit-cell volume) occupied by disordered solvent molecules.
Conclusions:
- The crystallization solvent significantly influences the crystal packing and intermolecular interactions of N,N '-Dithiodiphthalimide.
- Solvate formation in specific solvents leads to the creation of inclusion channels within the crystal structure.
- The study highlights the structural diversity achievable for this compound based on crystallization conditions.