5,6-Dichloro-2-(2-hydroxy-phen-yl)-iso-indoline-1,3-dione
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
The crystal structure of a dichlorophthalimide derivative reveals a nearly planar phthalimide ring system. Molecules are linked by hydrogen bonds and chlorine-oxygen interactions, forming a stable 3D network with pi-pi stacking.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Phthalimide derivatives are important in various chemical applications.
- Understanding the crystal packing and intermolecular interactions is crucial for material properties.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(14)H(7)Cl(2)NO(3).
- To analyze the intermolecular interactions governing the 3D network formation.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonds (C-H⋯O, O-H⋯O) and halogen bonds (C-Cl⋯O) was performed.
- Identification of weak π-π interactions contributing to structural stability.
Main Results:
- The phthalimide ring system exhibits near planarity with a dihedral angle of 4.02(3)°.
- Intermolecular hydrogen bonds and C-Cl⋯O contacts link molecules into a 3D network via specific ring motifs (R(2)(16), R(4)(19), R(4)(22)).
- Weak π-π interactions between phthalimide rings (centroid-centroid distance 3.666(3) Å) further stabilize the crystal structure.
Conclusions:
- The crystal structure is stabilized by a combination of hydrogen bonding, halogen bonding, and π-π interactions.
- The detailed analysis provides insights into the supramolecular assembly of dichlorophthalimide derivatives.
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