2-(1H-Benzimidazol-2-yl)-4-nitro-phenol
1College of Marine Sciences, Zhejiang Ocean University, Zhoushan 316000, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|April 28, 2011
Summary
Researchers synthesized a novel compound, C(13)H(9)N(3)O(3), revealing its near-planar structure and hydrogen bonding in dimers. This study details the molecular arrangement and crystal packing of the synthesized molecule.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- 5-nitro-salicyl-aldehyde and 1,2-diamino-benzene are key precursors in organic synthesis.
- Benzimidazole derivatives exhibit diverse biological and material properties.
- Understanding molecular planarity and hydrogen bonding is crucial for predicting compound behavior.
Purpose of the Study:
- To synthesize and characterize a novel compound with the molecular formula C(13)H(9)N(3)O(3).
- To investigate the molecular structure, including planarity and dihedral angles.
- To analyze the intermolecular interactions, specifically hydrogen bonding, in the crystalline state.
Main Methods:
- Chemical synthesis involving the reaction of 5-nitro-salicyl-aldehyde with 1,2-diamino-benzene in methanol.
- X-ray crystallography to determine the precise three-dimensional structure of the compound.
- Analysis of bond lengths, bond angles, and intermolecular forces within the crystal lattice.
Main Results:
- The synthesized compound C(13)H(9)N(3)O(3) was successfully prepared.
- The molecule exhibits approximate planarity, with a mean deviation of 0.0311(4) Å from its defined plane.
- A dihedral angle of 1.1(3)° was observed between the benzene and benzimidazole ring systems.
- Intra-molecular O-H⋯N hydrogen bonding was identified.
- Inter-molecular N-H⋯O hydrogen bonds link adjacent molecules into centrosymmetric dimers in the crystal structure.
Conclusions:
- The study successfully synthesized and characterized a new C(13)H(9)N(3)O(3) compound.
- The molecular structure is nearly planar, with specific dihedral angles between its ring systems.
- The crystal packing is dominated by intra- and inter-molecular hydrogen bonds, forming dimers.
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