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Triclinic polymorph of sulfasalazine
L A Filip1, M R Caira, S I Fărcaş
1University of Medicine and Pharmacy, Iuliu Hatieganu, Department of Drugs Control, Cluj-Napoca RO-3400, Romania.
Summary
This study details the crystal structure of a modified salicylic acid compound, revealing its amide tautomeric form and stabilizing hydrogen bonds. The planar molecule forms centrosymmetric dimers through hydrogen bonding and pi-pi stacking interactions.
Area of Science:
- Crystallography
- Molecular structure analysis
- Organic chemistry
Background:
- The title compound, 5-(4-[(2-pyridylamino)sulfonyl]phenyldiazenyl)salicylic acid, is a modified salicylic acid derivative.
- Understanding the solid-state structure and intermolecular interactions is crucial for predicting material properties.
Purpose of the Study:
- To elucidate the crystal structure of the modified salicylic acid compound.
- To identify the predominant tautomeric form and analyze stabilizing interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks and pi-pi stacking interactions was performed.
Main Results:
- The molecule exists in the amide tautomeric form in the crystal.
- A centrosymmetric dimer is the repeating unit, stabilized by hydrogen bonds involving carboxylic acid and pyridylamino groups.
- Intramolecular hydrogen bonding and intermolecular pi-pi stacking further stabilize the crystal structure.
Conclusions:
- The crystal structure reveals a stable arrangement of the modified salicylic acid derivative.
- Hydrogen bonding and pi-pi stacking are key factors governing the self-assembly and stability of this compound in the solid state.