Browse
Submit Data
Databases
API
Help

Dataset Information

38 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy-droxy-4-methyl-anilino)-methyl-idene]-4-methyl-cyclo-hexa-2,4-dien-1-one.

ABSTRACT: The title compound, C₁₅H₁₅NO₂, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. The mol-ecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intra-molecular N-H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O-H⋯O hydrogen bonds link adjacent mol-ecules into inversion dimers with an R ² ₂(18) ring motif. The dimers are linked by very weak π-π inter-actions, forming layers parallel to (01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol-ecular electrostatic potential surfaces were used to analyse the inter-molecular inter-actions, indicating that the most important contributions for the crystal packing are from H⋯H (55.2%), C⋯H/H⋯C (22.3%) and O⋯H/H⋯O (13.6%) inter-actions.

SUBMITTER: Kansiz S

PROVIDER: S-EPMC6658948 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

6-[(2,4-Di-methyl-anilino)methyl-idene]-2-hy-droxy-cyclo-hexa-2,4-dienone.

Project description:In the title compound, C15H15NO2, the dihedral angle between the aromatic rings is 5.86 (6)°, and an intra-molecular N-H⋯O hydrogen bond generates an S(6) motif, which helps to stabilize the enamine-keto tautomer. An intra-molecular O-H⋯O hydrogen bond also occurs. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(10) loops. A C-H⋯O inter-action links the dimers into [010] chains and aromatic π-π stacking [centroid-centroid separation = 3.6131 (9) Å] also occurs.

| S-EPMC3685031 | biostudies-literature

Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one.

Project description:In the title compound, C20H17NO3, the methyl-idene-cyclo-hexa-2,4-dienone moiety is approximately planar [maximum deviation = 0.0615?(10)?Å] and is oriented at diherdral angles of 69.60?(7) and 1.69?(9)° to the phenyl and hy-droxy-benzene rings, respectively. The amino group links with the carbonyl O atom via an intra-molecular N-H?O hydrogen bond, forming an S(6) ring motif. In the crystal, the mol-ecules are linked by O-H?O hydrogen bonds and weak C-H?O and C-H?? inter-actions, forming a three-dimensional supra-molecular architecture.

| S-EPMC4257387 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (<i>Z</i>)-6-[(2-hy-droxy-5-nitro-anilino)methyl-idene]-4-methyl-cyclo-hexa-2,4-dien-1-one.

Project description:The title compound, C14H12N2O4, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. The mol-ecule is almost planar, the rings making a dihedral angle of 4.99 (7)°. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, inversion-related mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming dimers with an R 2 2(18) ring motif. The dimers are linked by pairs of C-H⋯O contacts with an R 2 2(10) ring motif, forming ribbons extended along the [20] direction. Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol-ecular electrostatic potential surfaces were used to analyse the inter-molecular inter-actions present in the crystal, indicating that the most important contributions for the crystal packing are from H⋯H (33.9%), O⋯H/H⋯O (29.8%) and C⋯H/H⋯C (17.3%) inter-actions.

| S-EPMC6658968 | biostudies-literature

3-Diethyl-amino-6-[(Z)-(4-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dienone.

Project description:In the mol-ecule of the title compound, C(17)H(20)N(2)O(2), the aromatic rings are oriented at a dihedral angle of 6.23 (22)°. Intra-molecular N-H⋯O hydrogen bonding involving the amine H atom and the carbonyl O atom affects the conformation of the mol-ecule. One of the ethyl arms is disordered over two conformations, with occupancies of 0.59 (2) and 0.41 (2). The crystal packing is stabilized by inter-molecular C-H⋯O and O-H⋯O hydrogen bonds, and weak C-H⋯π inter-actions.

| S-EPMC3011427 | biostudies-literature

(6Z)-4-Bromo-6-{[(2-hy-droxy-eth-yl)amino]-methyl-idene}cyclo-hexa-2,4-dien-1-one.

Project description:The title mol-ecule, C(9)H(10)BrNO(2), excluding methyl-ene H atoms and the C-OH group, is essentially planar, with a maximum deviation of 0.037 (2) Å for the N atom. The N-C-C-O torsion angle is -63.1 (3)°. The mol-ecular structure is stabilized by a weak intra-molecular N-H⋯O(carbonyl) hydrogen bond, forming an S(6) motif. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

| S-EPMC3343984 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of a Schiff base: (<i>Z</i>)-6-[(5-chloro-2-meth-oxy-anilino)methyl-idene]-2-hy-droxy-cyclo-hexa-2,4-dien-1-one.

Project description:The title compound, C14H12ClNO3, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the mol-ecule is stabilized by a strong intra-molecular N-H⋯O hydrogen bond. In the crystal, pairs of centrosymmetrically related mol-ecules are linked by O-H⋯O hydrogen bonds, forming R 2 2(10) rings. Besides this, the mol-ecules form stacks along the [001] direction with C-H⋯π and C-H⋯Cl contacts between the stacks. The inter-molecular inter-actions in the crystal were analysed using Hirshfeld surfaces. The most significant contribution to the crystal packing is from H⋯H contacts (30.8%).

| S-EPMC6399700 | biostudies-literature

Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-5-methyl-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one.

Project description:In the title Schiff base compound, C21H19NO3, the conformation about the C=C bond is Z. The N-H group and carbonyl O atom form an intra-molecular N-H?O hydrogen bond with an S(6) ring motif. The benz-yloxy ring and the 2-hy-droxy-5-methyl-phenyl ring are inclined to the central six-membered ring by 13.68?(9) and 9.13?(8)°, respectively, and to one another by 21.95?(9)°. In the crystal, mol-ecules are linked by O-H?O hydrogen bonds, forming helical chains along [010].

| S-EPMC4186113 | biostudies-other

2,4-Dibromo-6-[(quinolin-8-yl-amino)-methyl-idene]cyclo-hexa-2,4-dien-1-one monohydrate.

Project description:In the title compound, C(16)H(10)Br(2)N(2)O·H(2)O, bifurcated intra-molecular N-H⋯(N,O) hydrogen bonding defines the essential planarity of the main mol-ecule: the dihedral angle between the quinoline and benzene rings is 7.53 (8)°. Inter-molecular O-H⋯O and weak C-H⋯O hydrogen bonds consolidate the crystal packing, which exhibits π-π inter-actions with a distance of 3.588 (1) Å between the centroids of the aromatic rings and short Br⋯Br contacts of 3.5757 (6) Å.

| S-EPMC3239023 | biostudies-literature

4-Nitro-6-[(8-quinolyl-amino)-methyl-idene]cyclo-hexa-2,4-dien-1-one.

Project description:The mol-ecule of the title compound, C(16)H(11)N(3)O(3), exists in the keto form and the C=O and N-H bonds are mutually cis in the crystal structure. There are two crystallographically independent mol-ecules per asymmetric unit with broadly similar structural data. The only noticeable difference between the two is the dihedral angles between the benzene and the quinoline rings: 1.04?(4) and 3.07?(4)°. In the structure, intra-molecular N-H?O(carbon-yl) and N-H?N(pyridine) hydrogen bonds exist but there is no evidence of formal inter-molecular hydrogen-bonding associations.

| S-EPMC3007437 | biostudies-literature

3-[1-(2-Hy-droxy-anilino)ethyl-idene]-3H-chromen-2,4-dione.

Project description:The title compound is a new amino-coumarin derivative, C17H13NO4, and was synthesized by the condensation of 2-amino-phenol and 3-acetyl-4-hy-droxy-coumarin. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, the molecules are linked into chains extending in the [010] direction by O-H?O hydrogen bonds. There is also a ?-? stacking inter-action between the bicyclic coumarin fragment and the phenol ring [centroid-centroid distance = 3.7510?(14)?Å], and these ring systems form between them a dihedral angle of 53.3?(2)°. Intermolecular hydrogen bond C-H?O hydrogen bonding is also observed in the interconnection of the crystal packing.

| S-EPMC3793787 | 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