Crystal structure of 6-bromo-7-fluoro-4-oxo-4 H-chromene-3-carbaldehyde

Abstract

In the crystal of this brominated and fluorinated 3-formyl­chromone derivative, mol­ecules are linked through stacking inter­actions, C—H⋯O hydrogen bonds and short C⋯O contacts. Unsymmetrical halogen⋯halogen inter­actions between the bromine and fluorine atoms are also formed, giving a meandering two-dimensional network propagating in the (041) plane.

Abstract

In the title compound, C ₁₀H ₄BrFO ₃, a brominated and fluorinated 3-formyl­chromone derivative, all atoms are essentially coplanar (r.m.s. deviation of 0.025 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.050 (6) Å] being for a benzene-ring C atom. In the crystal, mol­ecules are linked through stacking inter­actions [centroid–centroid distance between the benzene and pyran rings = 3.912 (4) Å], C—H⋯O hydrogen bonds and short C⋯O contacts [2.865 (7) Å]. Unsymmetrical halogen⋯halogen inter­actions between the bromine and fluorine atoms [Br⋯F = 3.116 (4) Å, C—Br⋯F = 151.8 (2), C—F⋯Br = 154.1 (4)°] are also formed, giving a meandering two-dimensional network propagating in the (041) plane. A comparison with related structures is made and the various types of weak inter­actions are ranked in importance.