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

ABSTRACT: In the title compound, C10H4BrFO3, a brominated and fluorinated 3-formyl-chromone 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, mol-ecules are linked through stacking inter-actions [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 inter-actions 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 inter-actions are ranked in importance.

SUBMITTER: Ishikawa Y

PROVIDER: S-EPMC4518968 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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

Ishikawa Yoshinobu Y

Acta crystallographica. Section E, Crystallographic communications 20150627 Pt 7

In the title compound, C10H4BrFO3, a brominated and fluorinated 3-formyl-chromone 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, mol-ecules are linked through stacking inter-actions [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]. Unsymmetr ...[more]

PMID: 26279885

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Crystal structure of 8-bromo-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H5BrO3, a brominated 3-formyl-chromone, all atoms are essentially coplanar (r.m.s. = 0.0104 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.028 (5) Å] being for one of the benzene C atoms. In the crystal, mol-ecules are linked through C-H⋯O hydrogen bonds, which are further assembled by face-to-face π-π stacking inter-actions [centroid-centroid distance between the pyran rings = 3.854 (4) Å]. Shorter contacts than the sum of van der Waals radii are observed between the Br and formyl O atoms [Br⋯O = 3.046 (4) Å, C-Br⋯O = 175.23 (18)° and Br⋯O-C = 132.6 (3)°], features that do indicate halogen bonding.

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

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Project description:In the title compound, C10H4ClFO3, a chlorinated and fluorinated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. = 0.0336 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.062 (2) Å] being for a benzene-ring C atom. In the crystal, mol-ecules are linked through stacking inter-actions [centroid-centroid distance between the benzene and pyran rings = 3.958 (3) Å and inter-planar distance = 3.259 (3) Å], C-H⋯O hydrogen bonds, and short C⋯O contacts [2.879 (3) Å]. Unsymmetrical halogen-halogen inter-actions between the Cl and F atoms [Cl⋯F = 3.049 (3) Å, C-Cl⋯F = 148.10 (9)° and C-F⋯Cl = 162.06 (13)°] are also formed, giving a meandering two-dimensional network along the a axis.

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Crystal structure of 7,8-di-chloro-4-oxo-4H-chromene-3-carbaldehyde.

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8-Chloro-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H5ClO3, a chlorinated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. deviation = 0.032 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.0598 (14) Å] being for a pyran-ring C atom. In the crystal, mol-ecules are linked through stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.566 (2) Å].

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6-Iodo-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H5IO3, an iodinated 3-formyl-chromone derivative, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0259 Å), with the largest deviation from the least-squares plane [0.056 (5) Å] being found for the formyl O atom. In the crystal, mol-ecules are linked through I⋯O halogen bonds [I⋯O = 3.245 (4) Å, C-I⋯O = 165.95 (13) and C=O⋯I = 169.7 (4)°] along [101]. The supra-molecular chains are assembled into layers via π-π stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.558 (3) Å].

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6-Methyl-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C(11)H(8)O(3), the benzopyran-4-one or chromone ring system is almost planar, with a maximum deviation of 0.045 (2) Å. The crystal structure is stablized by π-π inter-actions between the benzene and pyran rings of inversion-related mol-ecules stacked along the b axis, with a centroid-centroid distance of 3.5463 (12) Å

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