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3-Bromo-2-hy-droxy-benzaldehyde
Jessica B Metlay1, Joseph M Tanski
1Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.
Acta Crystallographica. Section E, Structure Reports Online
|August 21, 2012
Summary
This study reveals the near-planar structure of a novel brominated organic compound, C(7)H(5)BrO(2). It features intramolecular hydrogen bonding and intermolecular interactions like C-H⋯Br bonds and pi-stacking, influencing crystal packing.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the solid-state structure of organic molecules is crucial for predicting their properties.
- Intramolecular and intermolecular interactions dictate crystal packing and material characteristics.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C(7)H(5)BrO(2).
- To analyze the factors governing the molecular arrangement in the solid state.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
- Analysis of non-covalent interactions, including hydrogen bonding and pi-stacking, was performed.
Main Results:
- The molecule C(7)H(5)BrO(2) exhibits a nearly planar conformation with a root-mean-square deviation of 0.0271 Å.
- Intramolecular hydrogen bonding was observed between the phenolic hydroxyl group and the aldehyde oxygen atom.
- Crystal packing is influenced by weak intermolecular C-H⋯Br interactions and pi-stacking between adjacent molecules (dihedral angle 5.30(6)°, centroid-centroid distance 3.752(1) Å).
Conclusions:
- The title compound possesses a well-defined, nearly planar structure stabilized by intramolecular hydrogen bonding.
- Intermolecular C-H⋯Br interactions and pi-stacking play a significant role in directing the crystal packing, leading to a specific supramolecular arrangement.
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