Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of (E)-2-{[(4-anilinophen-yl)imino]meth-yl}-4-nitro-phenol.

ABSTRACT: In the title compound, C₁₉H₁₅N₃O₃, which crystallizes as the phenol-imine tautomer, the dihedral angle between the aromatic rings bridged by the NH unit is 47.16 (16)°. The dihedral angle between the rings bridged by the imine unit is 6.24 (15)°; this near coplanarity is reinforced by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring. In the crystal, N-H⋯O hydrogen bonds generate [201] C(13) chains. The chains are reinforced and cross-linked by C-H⋯O inter-actions to generate (001) sheets.

SUBMITTER: Faizi MS

PROVIDER: S-EPMC5290545 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure of (E)-2-{[(4-anilinophen-yl)imino]meth-yl}-4-nitro-phenol.

Faizi Md Serajul Haque MS Haque Ashanul A Kalibabchuk Valentina A VA

Acta crystallographica. Section E, Crystallographic communications 20170106 Pt 2

In the title compound, C19H15N3O3, which crystallizes as the phenol-imine tautomer, the dihedral angle between the aromatic rings bridged by the NH unit is 47.16 (16)°. The dihedral angle between the rings bridged by the imine unit is 6.24 (15)°; this near coplanarity is reinforced by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring. In the crystal, N-H⋯O hydrogen bonds generate [201] C(13) chains. The chains are reinf ...[more]

PMID: 28217322

Similar Datasets

Crystal structure of (E)-5-benz-yloxy-2-{[(4-nitro-phen-yl)imino]-meth-yl}phenol.

Project description:In the title compound, C20H16N2O4, the mol-ecule adopts an E conformation about the N=C bond. There is an intra-molecular O-H⋯N hydrogen bond forming an S(6) ring motif. The nitro-benzene and benz-yloxy rings are inclined to the central benzene ring by 4.34 (10) and 27.66 (11)°, respectively, and to one another by 31.40 (12)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming zigzag chains along [001]. Within the chains there are C-H⋯π inter-actions present. The chains are linked via π-π inter-actions [inter-centroid distance = 3.7048 (15) Å], forming slabs parallel to the bc plane.

| S-EPMC4719944 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 2-{[(4-iodo-phen-yl)imino]-meth-yl}-4-nitro-phenol.

Project description:The title compound, C13H9IN2O3, was synthesized by a condensation reaction between 2-hy-droxy-5-nitro-benzaldehyde and 4-iodo-aniline, and crystallizes in the ortho-rhom-bic space group Pna21. The 4-iodo-benzene ring is inclined to the phenol ring by a dihedral angle of 39.1 (2)°. The configuration about the C=N double bond is E. The crystal structure features C-H⋯O hydrogen-bonding inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are O⋯H/H⋯O (26.9%) and H⋯H (22.0%) inter-actions.

| S-EPMC7336806 | biostudies-literature

Crystal structure of (E)-2-{[(4-anilinophen-yl)imino]-meth-yl}phenol.

Project description:The title compound, C19H16N2O, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. There is an intra-molecular O-H⋯N hydrogen bond in each mol-ecule with the phenol ring being inclined to the central benzene ring by 4.93 (14) and 7.12 (14)° in mol-ecules A and B, respectively. The conformation of the two mol-ecules differs essentially in the orientation of the terminal amino-phenyl ring with respect to the central benzene ring; this dihedral angle is 50.51 (4)° in mol-ecule A and 54.61 (14)° in mol-ecule B. The two outer aromatic rings are inclined to one another by 51.39 (14) and 49.88 (14)° in mol-ecules A and B, respectively. In the crystal, mol-ecules are connected by N-H⋯O hydrogen bonds generating -A-B-A-B- zigzag chains extending along [010]. The chains are linked via C-H⋯π inter-actions involving neighbouring A mol-ecules, forming slabs lying parallel to (100).

| S-EPMC4331856 | biostudies-literature

Crystal structure of 2-{[(2-chloro-phen-yl)imino]-meth-yl}phenol.

Project description:In the title compound, C13H10ClNO, the dihedral angle between the planes of the aromatic rings is 51.42 (9)° and an intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. The Cl atom and the N atom are syn. No directional inter-actions beyond van der Waals contacts are observed in the crystal.

| S-EPMC4331896 | biostudies-literature

2-[(4-Meth-oxy-2-nitro-phen-yl)imino-meth-yl]phenol.

Project description:The crystal structure of the title compound, C(14)H(12)N(2)O(4), contains four crystallographically independent mol-ecules in the asymmetric unit. All the mol-ecules have similar conformations; the dihedral angles between the aromatic rings are 33.1 (1), 33.76 (9), 31.41 (9) and 32.56 (10)°. Intra-molecular O-H⋯N hydrogen bonds form S(6) ring motifs in each molecule. In the crystal, there are two pairs of pseudo-inversion-related mol-ecules. Along the c axis, mol-ecules are stacked with π-π inter-actions between the 2-hy-droxy-phenyl and 4-meth-oxy-2-nitro-phenyl rings [centroid-centroid distances = 3.5441 (12)-3.7698 (12) Å].

| S-EPMC3414359 | biostudies-literature

2-[(4-Methoxy-phen-yl)imino-meth-yl]-4-nitro-phenol.

Project description:The title Schiff base compound, C(14)H(12)N(2)O(4), is in an inter-mediate state between NH and OH tautomers. Apart from the intra-molecular O-H⋯N hydrogen bond, there are inter-molecular C-H⋯O hydrogen bonds, generating centrosymmetric R(2) (2)(18) and R(2) (2)(14) dimers.

| S-EPMC2968952 | biostudies-literature

2-{(E)-[(2-Methyl-3-nitro-phen-yl)imino]-meth-yl}-4-nitro-phenol.

Project description:The title compound, C14H11N3O5, is a Schiff base that adopts the enol-imine tautomeric form in the solid state. The dihedral angle between the aromatic rings is 37.4?(3)° and the dihedral angles between the nitro groups and their attached rings are 4.0?(6) and 46.2?(8)°. The mol-ecular structure is stabilized by an intra-molecular O-H?N hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by C-H?O interactions, forming a two-dimensional network parallel to the bc plane.

| S-EPMC3770363 | biostudies-literature

(E)-2-{[(Furan-2-ylmeth-yl)imino]-meth-yl}-4-nitro-phenol.

Project description:In the title compound, C12H10N2O4, the furan-2-ylmethyl group is disordered over two sets of sites, with refined occupancies of 0.858 (3) and 0.143 (3). In the major component of disorder, the dihedral angle between the furan and benzene rings is 63.1 (2)° and for the minor component this value is 67.9 (6)°. The planes of the nitro group and the attached benzene ring form a dihedral angle of 4.34 (17)°. In the crystal, inversion-related mol-ecules are linked by two pairs of weak C-H⋯O inter-actions, one involving the nitro group and the other involving the O-H group as an acceptor. As a result of these associations, ribbons are formed along [120]. A strong intra-molecular O-H⋯N hydrogen bond is observed.

| S-EPMC3998629 | biostudies-literature

Crystal structure of (E)-4-meth-oxy-2-{[(5-methyl-pyridin-2-yl)imino]-meth-yl}phenol.

Project description:The mol-ecule of the title Schiff base compound, C14H14N2O2, displays an E conformation with respect the imine C=N double bond. The mol-ecule is approximately planar, with the dihedral angle formed by the planes of the pyridine and benzene rings being 5.72 (6)°. There is an intra-molecular hydrogen bond involving the phenolic H and imine N atoms.

| S-EPMC4645057 | biostudies-literature

4-Bromo-2-[(E)-{[4-nitro-2-(trifluoro-meth-yl)phen-yl]imino}-meth-yl]phenol.

Project description:Except two F atoms of the -CF(3) group, the title compound, C(14)H(8)BrF(3)N(2)O(3), has an almost planar conformation, the dihedral angle between the aromatic rings being 3.60 (16)°. The mol-ecule adopts the enol-imine tautomeric form, with an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. In the crystal, face-to-face π-π stacking [centroid-centroid distances = 3.669 (2) and 3.732 (2) Å] between the aromatic rings of the mol-ecules, which lie in sheets parallel to (202), help to establish the packing.

| S-EPMC3515262 | biostudies-literature