2-{(E)-[(2-Methyl-3-nitro-phen-yl)imino]-meth-yl}-4-nitro-phenol
Hasan Tanak1, Ferhat Toğurman, Sedanur Kalecik
1Department of Physics, Faculty of Arts & Science, Amasya University, Ipekkoy-Amasya, Turkey.
Acta Crystallographica. Section E, Structure Reports Online
|September 19, 2013
Summary
This study characterizes a novel Schiff base, C14H11N3O5, revealing its solid-state enol-imine tautomerism. Molecular structure analysis highlights specific dihedral angles and hydrogen bonding interactions, forming a 2D crystal network.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- Understanding tautomerism is crucial for predicting chemical properties.
- Crystal engineering aims to design materials with specific structures and functions.
Purpose of the Study:
- To determine the solid-state structure of the title Schiff base (C14H11N3O5).
- To investigate the tautomeric form and molecular conformation.
- To analyze intermolecular interactions and crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to elucidate the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles.
- Identification of hydrogen bonding and other non-covalent interactions.
Main Results:
- The compound exists in the enol-imine tautomeric form in the solid state.
- Significant dihedral angles between aromatic rings (37.4°) and nitro groups (4.0°, 46.2°).
- Intramolecular O-H⋯N hydrogen bond forms an S(6) ring, stabilizing the molecule.
- Intermolecular C-H⋯O interactions link molecules into a 2D network parallel to the bc plane.
Conclusions:
- The study provides detailed structural insights into a novel Schiff base.
- The observed tautomerism and hydrogen bonding influence the crystal packing.
- The formation of a 2D network suggests potential for materials with layered structures.
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