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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 |

REPOSITORIES: biostudies-literature

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

Project description:In the title compound, C10H5BrO3, a brominated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. = 0.0631?Å for the non-H atoms), with the largest deviation from the least-squares plane [0.215?(3)?Å] being for the formyl O atom. In the crystal, mol-ecules are linked into tapes through C-H?O hydrogen bonds and these tapes are assembled by stacking inter-actions [centroid-centroid distance between the pyran rings = 3.858?(3)?Å] to form supra-molecular layers that stack along the c axis.

| S-EPMC4186120 | biostudies-literature

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.

| S-EPMC4571403 | biostudies-literature

6,8-Di-bromo-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H4Br2O3, the atoms of the 6,8-di-bromo-chromone unit are essentially coplanar [largest deviation from the mean planes = 0.1109 (3) Å] and the formyl group is twisted slightly with respect to the attached ring [C-C-C-O torsion angles = 11.5 (4) and -168.9 (3)°]. In the crystal, mol-ecules are linked to each other through halogen bonds [Br⋯O = 3.118 (2) Å, C-Br⋯O = 162.37 (8) and C=O⋯Br = 140.20 (15)°]. The molecules are further assembled via π-π stacking interactions [centroid-centroid distance = 3.850 (2) Å].

| S-EPMC3998586 | biostudies-literature

6-Chloro-7-fluoro-4-oxo-4H-chromene-3-carbaldehyde.

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.

| S-EPMC4120572 | biostudies-literature

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

Project description:In the title compound, C10H4Cl2O3, a dichlorinated 3-formyl-chromone derivative, the fused-ring system is slightly puckered [dihedral angle between the benzene and pyran rings = 3.66 (10)°]. The dihedral angle between the pyran ring and the formyl plane is 8.64 (7)°. In the crystal, mol-ecules are linked through π-π stacking inter-actions [centroid-centroid distance between the benzene and pyran rings = 3.727 (2) Å], C-H⋯O hydrogen bonds and short C⋯O contacts [2.838 (4) Å]. Halogen bonds between the formyl O atoms and the Cl atoms at the 7-position [Cl⋯O = 2.984 (3) Å, C-Cl⋯O = 170.83 (12)° and Cl⋯O-C = 116.05 (19)°] are also formed along the a axis, resulting in helical structures constructed by C-H⋯O hydrogen bonds and Cl⋯O halogen bonds along the b axis. In addition, type II halogen-halogen contacts between the chlorine atoms at the 7- and 8-positions [Cl⋯Cl = 3.519 (2) Å, C-Cl⋯Cl = 171.24 (10)° and 88.74 (11)°] are observed.

| S-EPMC4571352 | biostudies-literature

Crystal structure of 6,7-di-chloro-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H4Cl2O3, a dichlorinated 3-formyl-chromone, the non-H atoms of the 4H-chromene ring are essentially coplanar (r.m.s. = 0.0188 Å), with the largest deviation from the least-squares plane [0.043 (2) Å] being for the pyran C=O C atom. The α,β-unsaturated carbonyl O atom deviates from the least-square plane by 0.124 (2) Å. The dihedral angle between the chromone and formyl least-square planes is 6.76 (3)°. In the crystal, mol-ecules are linked through C-H⋯O hydrogen bonds between the translation-symmetry and inversion-symmetry equivalents to form tetrads, which are further assembled by stacking inter-actions [centroid-centroid distance between the benzene rings = 3.769 (2) Å]. van der Waals contacts are found between the Cl atoms at the 6-position and the Cl atoms at 7-position of the glide-reflection-symmetry equivalents [Cl⋯Cl = 3.4785 (16) Å, C-Cl⋯Cl = 160.23 (7)° and Cl⋯Cl-C = 122.59 (7)°].

| S-EPMC4555387 | biostudies-literature

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 ?-? 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

| S-EPMC3470266 | biostudies-literature

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].

| S-EPMC4120543 | biostudies-literature

7-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 = 0.0592?Å for all non-H atoms), with the largest deviation from the least-squares plane [0.1792?(19)?Å] being for the chromone-ring carbonyl O atom. In the crystal, mol-ecules are linked through C-H?O hydrogen bonds to form tetrads, which are assembled by stacking inter-actions [centroid-centroid distance between the pyran rings = 3.823?(3)?Å] and van der Waals contacts between the Cl atoms [Cl?Cl = 3.4483?(16)?Å and C-Cl?Cl = 171.73?(7)°] into a three-dimensional architecture.

| S-EPMC4158550 | biostudies-literature

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 ?-? stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.558?(3)?Å].

| S-EPMC4120610 | biostudies-literature

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