Browse
Submit Data
Databases
API
Help

Dataset Information

16 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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.

ABSTRACT: 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.

SUBMITTER: Beemarao M

PROVIDER: S-EPMC6829740 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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.

Beemarao M M Silambarasan S S Nasser A Jamal Abdul AJA Purushothaman M M Ravichandran K K

Acta crystallographica. Section E, Crystallographic communications 20191022 Pt 11

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 Hirshf ...[more]

PMID: 31709082

Similar Datasets

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 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 ?-? stacking inter-action is observed; the centroid-to-centroid distance is 3.7260?(7)?Å.

| S-EPMC4571389 | 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?? 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

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. ?-? 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?? inter-action is present in the crystal.

| S-EPMC3297294 | 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

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 MEP study of (E)-2-[(2-hy-droxy-5-meth-oxy-benzyl-idene)amino]-benzo-nitrile.

Project description:The asymmetric unit of the title compound, C15H12N2O2, contains two crystallographically independent mol-ecules in which the dihedral angles between the benzene rings in each are 13.26?(5) and 7.87?(5)°. An intra-molecular O-H?N hydrogen bonds results in the formation of an S(6) ring motif. In the crystal, mol-ecules are linked by weak C-H?O and C-H?N hydrogen bonds, forming layers parallel to (011). In addition, ?-? stacking inter-actions with centroid-centroid distances in the range 3.693?(2)-3.931?(2)?Å complete the three-dimensional network.

| S-EPMC6659330 | biostudies-literature

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

Project description: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?? inter-actions also contribute to this arrangement. The layers are linked by weak by C-H?? and ?-? [inter-centroid separation = 3.8713?(7)?Å] inter-actions.

| S-EPMC4571384 | biostudies-other

6-Hy-droxy-1,2-dihydro-4H-pyrrolo-[3,2,1-ij]quinolin-4-one.

Project description:The mol-ecule of the title compound, C11H9NO2, is essentially planar [r.m.s. deviation of the non-H atoms = 0.056?(1)?Å]. In the crystal, strong O-H?O hydrogen bonds form zigzag chains along the b axis. The mol-ecules form stacks along the a axis due to ?-? inter-actions, the shortest distance between the centroids of the benzene and pyridinone rings being 3.6146?(7)?Å.

| S-EPMC3588512 | biostudies-literature

3,3'-Dihy-droxy-6,6'-bis-(hy-droxy-meth-yl)-2,2'-(pentane-1,1-di-yl)di-4H-pyran-4-one.

Project description:In the title mol-ecule, C(17)H(20)O(8), the two pyran rings form a dihedral angle of 61.2?(2)°. The two hy-droxy-methyl groups are each disordered over two sets of sites in a 0.764?(3):0.236?(3) ratio. In the crystal, O-H?O hydrogen bonds link the mol-ecules into layers parallel to the ac plane.

| S-EPMC3344022 | biostudies-literature