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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
5-Fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol
Izabela D Madura1, Agnieszka Adamczyk-Woźniak, Michał Jakubczyk
1Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warszawa, Poland.
Acta Crystallographica. Section E, Structure Reports Online
|April 28, 2011
Summary
The crystal structure of AN2690, a broad-spectrum antifungal drug, reveals planar molecules forming dimers through hydrogen bonds. These dimers create layered structures with a unique two-dimensional network topology.
Area of Science:
- Crystallography
- Medicinal Chemistry
- Materials Science
Background:
- The compound C(7)H(6)BFO(2), known as AN2690, is a broad-spectrum antifungal agent.
- Understanding the crystal structure of pharmaceutical compounds is crucial for drug design and formulation.
Purpose of the Study:
- To elucidate the crystal structure of the antifungal drug AN2690.
- To characterize the intermolecular interactions and supramolecular assembly of AN2690 in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the crystal structure.
- Analysis of hydrogen bonding and other weak interactions was performed.
Main Results:
- The crystal structure consists of planar AN2690 molecules with a maximum deviation of 0.035(1) Å.
- Molecules form centrosymmetric R(2)(2)(8) dimers linked by strong O-H⋯O hydrogen bonds.
- Dimers are arranged into layers via weak intermolecular C-H⋯O and C-H⋯F hydrogen bonds, forming a two-dimensional network with a (4.4.4.4.6.6) topology.
- Further C-H⋯O interactions contribute to the three-dimensional structure.
Conclusions:
- The detailed crystal structure provides insights into the solid-state packing of AN2690.
- The identified hydrogen bonding patterns and network topology are key features of the antifungal drug's supramolecular assembly.
- This structural information can aid in understanding the drug's properties and potential for polymorphism.
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