Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of 3-amino-1-(4-hy-droxy-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

ABSTRACT: In the title compound, C20H14N2O2, the hy-droxy-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 85.56 (4)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular layer in the bc plane; N-H⋯π inter-actions also contribute to this arrangement. The layers are linked by weak by C-H⋯π and π-π [inter-centroid separation = 3.8713 (7) Å] inter-actions.

SUBMITTER: Akkurt M

PROVIDER: S-EPMC4571384 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure of 3-amino-1-(4-hy-droxy-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

Akkurt Mehmet M Horton Peter N PN Younes Sabry H H SH Mohamed Shaaban K SK Albayati Mustafa R MR

Acta crystallographica. Section E, Crystallographic communications 20150704 Pt 8

In the title compound, C20H14N2O2, the hy-droxy-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 85.56 (4)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular layer in the bc plane; N-H⋯π inter-actions also contribute to this arrangement. The layers are linked by weak by C-H⋯π and π-π [inter-centroid s ...[more]

PMID: 26396784

Similar Datasets

Crystal structure of 2-amino-7-hy-droxy-4-(4-hy-droxy-phen-yl)-4H-chromene-3-carbo-nitrile.

Project description:In the title compound, C16H12N2O3, the chromene ring system is nearly planar [maximum deviation from the mean plane = 0.057 (1) Å], and is almost perpendicular to the benzene ring, with a dihedral angle of 85.29 (5)°. In the crystal, mol-ecules are linked by classical N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds, and weak C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular network. Furthermore, a weak π-π stacking inter-action is observed; the centroid-to-centroid distance is 3.7260 (7) Å.

| S-EPMC4571389 | biostudies-literature

Crystal structure of 3-amino-1-(4-chloro-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

Project description:In the title compound, C20H13ClN2O, the chloro-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 81.26 (8)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, N-H⋯N hydrogen bonds generate chains along the b-axis direction. Further N-H⋯N hydrogen bonds link these chains into sheets parallel to (010). The crystal packing also features C-H⋯π inter-actions. The crystal studied was an inversion twin with a 0.557 (16):0.443 (16) domain ratio.

| S-EPMC4518915 | biostudies-literature

Crystal structure of 3-amino-1-(4-meth-oxy-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

Project description:In the title compound, C21H16N2O2, the meth-oxy-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 83.62 (5)°. The 4H-pyran ring fused with the naphthalene ring system is almost planar [maximum deviation = 0.033 (1) Å]. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯N hydrogen bonds. N-H⋯O hydrogen bonds connect the dimers, forming a helical supra-molecular chain along the a-axis direction. The crystal packing also features C-H⋯π inter-actions.

| S-EPMC4518947 | biostudies-literature

Crystal structure of 2-amino-4-(4-meth-oxy-phen-yl)-4H-benzo[g]chromene-3-carbo-nitrile.

Project description:In the title compound, C21H16N2O2, the naphthalene fragment is twisted slightly, as indicated by the dihedral angle of 3.2 (2)° between the two six-membered rings. The pendant 4-meth-oxy-phenyl ring makes a dihedral angle of 86.08 (6)° with the central six-membered ring of the 4H-benzo[g]chromene ring system. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers which are linked into chains propagating in the b-axis direction by N-H⋯O hydrogen bonds.

| S-EPMC4719954 | biostudies-literature

Crystal structure of 2-amino-4-phenyl-4H-benzo[h]chromene-3-carbo-nitrile.

Project description:In the title compound, C20H14N2O, the plane of the phenyl ring is almost normal to that of the naphthalene ring system, forming a dihedral angle of 83.15 (8)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers with an R 2 (2)(12) ring motif. The dimers are connected by C-H⋯π inter-actions, forming supra-molecular chains along [010].

| S-EPMC4518988 | biostudies-literature

Crystal structure, DFT and Hirshfeld surface analysis of 2-amino-4-(2-chloro-phen-yl)-7-hy-droxy-4H-benzo[1,2-b]pyran-3-carbo-nitrile.

Project description:The benzo-pyran ring of the title com-pound, C16H11ClN2O2, is planar [maximum deviation = 0.079 (2) Å] and is almost perpendicular to the chloro-phenyl ring [dihedral angle = 86.85 (6)°]. In the crystal, N-H⋯O, O-H⋯N, C-H⋯O and C-H⋯Cl hydrogen bonds form inter- and intra-molecular inter-actions. The DFT/B3LYP/6-311G(d,p) method was used to determine the HOMO-LUMO energy levels. The mol-ecular electrostatic potential surfaces were investigated by Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyse the inter-molecular inter-actions in the mol-ecule.

| S-EPMC6829740 | biostudies-literature

Crystal structure of 3-bromo-2-hy-droxy-benzo-nitrile.

Project description:The crystal structure of the title compound, C7H4BrNO, has been determined, revealing a partial mol-ecular packing disorder such that a 180° rotation of the mol-ecule about the phenol C-O bond results in disorder of the bromine and nitrile groups. The disorder has been parameterized as a disorder of only the bromine and nitrile substituents on a unique phenol ring. An intra-molecular O-H⋯Br contact occurs. In the crystal, O-H⋯Br/O-H⋯Nnitrile hydrogen bonding is present between the disordered bromine and nitrile substituents and the phenol group, forming a spiral chain about a twofold screw axis extending parallel to the b-axis direction. Within this spiral chain, the mol-ecules also inter-act, forming offset face-to-face π-stacking inter-actions with plane-to-centroid distance of 3.487 (1) Å.

| S-EPMC4518954 | biostudies-literature

4-{4-[(E)-(2-Hy-droxy-phen-yl)imino-methyl]phen-oxy}benzene-1,2-di-carbo-nitrile.

Project description:The asymmetric unit of the title compound, C(21)H(13)N(3)O(2), contains two independent mol-ecules with a similar structure. In one mol-ecule, the central benzene ring is oriented with respect to the terminal benzene rings at 27.23 (7) and 67.96 (7)°; in the other mol-ecule, the corresponding dihedral angles are 12.42 (7) and 64.55 (7)°. In both molecules, there is a short O-H⋯N interaction involving the OH group and the adjacent N atom. In the crystal, there are O-H⋯N hydrogen bonds, and C-H⋯O and N-H⋯O interactions linking the molecules to form a three-dimensional network. π-π stacking between the pyridine and benzene rings and between the benzene rings [centroid-centroid distances = 3.989 (2), 3.705 (2) and 3.607 (2) Å] may further stabilize the structure. A weak C-H⋯π inter-action is present in the crystal.

| S-EPMC3297294 | biostudies-literature

Crystal structures of two 4H-chromene derivatives: 2-amino-3-cyano-4-(3,4-di-chloro-phen-yl)-7-hy-droxy-4H-benzo[1,2-b]pyran 1,4-dioxane monosolvate and 2-amino-3-cyano-4-(2,6-di-chloro-phen-yl)-7-hy-droxy-4H-benzo[1,2-b]pyran.

Project description:In the title compounds, C16H9Cl2N2O2·C4H8O2 and C16H9Cl2N2O2, the bicyclic 4H-chromene cores are nearly planar with maximum deviations of 0.081?(2) and 0.087?(2)?Å. In both structures, the chromene derivative mol-ecules are linked into centrosymmetric dimers by pairs of N-H?O hydrogen bonds, forming R2 2 (16) motifs. These dimers are further linked in the 3,4-di-chloro-phenyl derivative by N-H?N hydrogen bonds into double layers parallel to (100) and in the 2,6-di-chloro-phenyl derivative by O-H?N hydrogen bonds into ribbons along the [10] direction. In the 3,4-di-chloro-phenyl derivative, the 1,4-dioxane solvent mol-ecules are connected to the chromene mol-ecules via O-H?O hydrogen bonds.

| S-EPMC6775756 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hy-droxy-5-methyl-benzyl-idene)amino]-benzo-nitrile.

Project description:The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 2-amino-benzo-nitrile, and crystallizes in the ortho-rhom-bic space group Pbca. The phenol ring is inclined to the benzo-nitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intra-molecular O-H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, C-H⋯O and C-H⋯N inter-actions lead to the formation of sheets perpendicular to the a axis. C-H⋯π inter-actions, forming polymeric chains along the a-axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H⋯H and C⋯H/H⋯C inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure and the HOMO-LUMO energy gap is given.

| S-EPMC7405566 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data