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

ABSTRACT: 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.

SUBMITTER: Ghichi N

PROVIDER: S-EPMC4719944 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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 ?-? 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

Crystal structures and anti-oxidant capacity of (E)-5-benz-yloxy-2-{[(4-chloro-phen-yl)imino]-meth-yl}phenol and (E)-5-benz-yloxy-2-({[2-(1H-indol-3-yl)eth-yl]iminium-yl}meth-yl)phenolate.

Project description:The title Schiff base compounds, C20H16ClNO2 (I) and C24H22N2O2 (II), were synthesized via the condensation reaction of 2-amino-4-chloro-phenol for (I), and 2-(2,3-di-hydro-1H-indol-3-yl)ethan-1-amine for (II), with 4-benz-yloxy-2-hy-droxy-benzaldehyde. In both compounds, the configuration about the C=N imine bond is E. Neither mol-ecule is planar. In (I), the central benzene ring makes dihedral angles of 49.91 (12) and 53.52 (11)° with the outer phenyl and chloro-phenyl rings, respectively. In (II), the central benzene ring makes dihedral angles of 89.59 (9) and 72.27 (7)°, respectively, with the outer phenyl ring and the mean plane of the indole ring system (r.m.s. deviation = 0.011 Å). In both compounds there is an intra-molecular hydrogen bond forming an S(6) ring motif; an O-H⋯O hydrogen bond in (I), but a charge-assisted N+-H⋯O- hydrogen bond in (II). In the crystal of (I), mol-ecules are linked by C-H⋯π inter-actions, forming slabs parallel to plane (001). In the crystal of (II), mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked by C-H⋯O hydrogen bonds, C-H⋯π inter-actions and a weak N-H⋯π inter-action, forming columns propagating along the a-axis direction. The anti-oxidant capacity of the synthesized compounds was determined by cupric reducing anti-oxidant capacity (CUPRAC) for compound (I) and by 2,2-picrylhydrazyl hydrate (DPPH) for compound (II).

| S-EPMC5946972 | 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

1-[(3-Benz-yloxy-2-nitro-phen-oxy)meth-yl]benzene.

Project description:The asymmetric unit of the title compound, C(20)H(17)NO(4), consists of two crystallographically independent mol-ecules. In one of the mol-ecules, the central benzene ring forms dihedral angles of 2.26?(6) and 58.68?(6)° with the terminal benzene rings and the dihedral angle between the terminal benzene rings is 56.45?(6)°. The corresponding values for the other mol-ecule are 35.17?(6), 70.97?(6) and 69.62?(6)°, respectively. In the crystal, an inversion dimer linked by a pair of C-H?O hydrogen bonds occurs for one of the unique mol-ecules. C-H?? and ?-? [centroid-centroid distances = 3.7113?(8) and 3.7216?(7)?Å] inter-actions link the components into a three-dimensional network.

| S-EPMC3414184 | 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

1-(4-Benz-yloxy-5-meth-oxy-2-nitro-phen-yl)ethanone.

Project description:In the mol-ecule of the title compound, C(16)H(15)NO(5), the aromatic rings are oriented at a dihedral angle of 74.89?(3)°. Intra-molecular C-H?O inter-actions result in the formation of a seven-membered ring. In the crystal structure, weak inter-molecular C-H?O inter-actions link the mol-ecules into chains along the b axis.

| S-EPMC2977694 | biostudies-literature

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

Project description:In the title Schiff base compound, C(15)H(15)NO(2), prepared from 4-meth-oxy-benzyl-amine and salicyl-aldehyde, an intra-molecular O-H?N hydrogen bonds influences the mol-ecular conformation; the two aromatic rings form a dihedral angle of 73.5?(1)°. In the crystal, weak inter-molecular C-H?O inter-actions link the mol-ecules into chains propagating in [010].

| S-EPMC3011435 | biostudies-literature

(E)-4-[(3,5-Dimethyl-phen-yl)imino-meth-yl]-2-meth-oxy-3-nitro-phenol.

Project description:The mol-ecule of the title compound, C(16)H(16)N(2)O(4), exists in the E configuration with respect to the central C=N double bond. The dihedral angle between the two benzene rings is 2.17?(9)?Å. In the crystal, mol-ecules are linked via O-H?N hydrogen bonds into chains that propagate along the b-axis direction. There is also ?-? stacking of inversion-related mol-ecules, with inter-planar spacings of 3.479?(5)?Å and ring centroid-centroid distances of 3.876?(4)?Å.

| S-EPMC3254553 | 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 ?-? 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

Crystal structure of (E)-2-({[2-(1,3-dioxan-2-yl)phen-yl]imino}-meth-yl)phenol.

Project description:The title compound, C17H17NO3, prepared by the condensation reaction of 2-(1,3-dioxan-2-yl)aniline and salicyl-aldehyde, has an E conformation about the C=N bond. The six-membered O-heterocycle adopts a chair conformation, with the bond to the aromatic ring located at its equatorial position. The dihedral angle between the aromatic rings is 36.54?(9)°. There is an intra-molecular N-H?O hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, forming chains along the a-axis direction. Within the chains, there are C-H?? inter-actions involving adjacent mol-ecules.

| S-EPMC4420126 | biostudies-literature

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