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

ABSTRACT: 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.

SUBMITTER: Kılıc I

PROVIDER: S-EPMC2968952 | 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

(E)-2-[(4-Ethoxy-phen-yl)imino-meth-yl]-4-methoxy-phenol.

Project description:In the mol-ecule of the title compound, C(16)H(17)NO(3), the aromatic rings are oriented at a dihedral angle of 29.25?(8)°. An intra-molecular O-H?N hydrogen bond results in the formation of a nearly planar [maximum deviation 0.034?(13)?Å] six-membered ring, which is oriented at dihedral angles of 0.91?(1) and 28.91?(12)° with respect to the aromatic rings. The title mol-ecule is a phenol-imine tautomer, as evidenced by C-O, C-N and C-C bond lengths. In the crystal, mol-ecules are linked by inter-molecular C-H?O hydrogen bonds that generate C(8) chains.

| S-EPMC2971308 | biostudies-literature

(E)-2-[(2-Ethyl-phen-yl)imino-meth-yl]-6-methoxy-phenol.

Project description:The mol-ecule of the title compound, C(16)H(17)NO(2), adopts the phenol-imine tautomeric form with a strong intra-molecular O-H?N hydrogen bond and an E conformation with respect to the azomethine C=N bond. The dihedral angle between the aromatic rings is 21.23?(9)°. The ethyl group is disordered over two orientations with occupancies of 0.598?(6) and 0.402?(6). In the crystal, the mol-ecules are linked into chains along the b axis by C-H?? inter-actions.

| S-EPMC2979675 | 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)-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

(E)-2-[(2-Amino-4,5-dibromo-phen-yl)imino-meth-yl]-6-methoxy-phenol.

Project description:The title compound, C(14)H(12)Br(2)N(2)O(2), was prepared from the condensation of 4,5-dibromo-1,2-phenyl-enediamine and 2-hydr-oxy-3-methoxy-benzaldehyde in methanol. The N=C double bond shows a trans conformation and the dihedral angle between the aromatic ring planes is 5.9?(4)°. In the crystal structure, there are intra-molecular O-H?N and N-H?N and inter-molecular N-H?O hydrogen bonds, the latter resulting in inversion dimers.

| S-EPMC2968274 | biostudies-literature

4-Chloro-2-[(E)-2-(4-methoxy-phen-yl)ethyl-imino-meth-yl]phenol.

Project description:In the title Schiff base, C(16)H(16)ClNO(2), the 2-(4-methoxy-phen-yl)ethyl (CH(3)OC(6)H(4)CH(2)CH(2)-; r.m.s. deviation = 0.10?Å) and 4-chloro-2-(imino-meth-yl)phenol (N=CHC(6)H(3)ClOH; r.m.s. deviation = 0.01?Å) portions are both essentially planar, the two parts being inclined at an angle of 61.8?(1)°. The hydroxy group forms a hydrogen bond to the imino N atom.

| S-EPMC2977750 | biostudies-literature

2-{[3-Chloro-4-(4-chloro-phen-oxy)phen-yl]imino-meth-yl}-4-nitro-phenol.

Project description:In the title compound, C19H12Cl2N2O4, the imine bond length of 1.257?(6)?Å is typical of a double bond. The dihedral angle between the para-nitro benzene ring and the central benzene ring is 12.06?(3)° and that between the central benzene and the para-chloro benzene ring is 73.81?(2)°. An intra-molecular O-H?N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked together by two pairs of C-H?O interactions (to the same O atom acceptor), forming inversion dimers. A short Cl?Cl contact [3.232?(4)?Å] is observed.

| S-EPMC3685046 | biostudies-literature

2-{(E)-[(4-Methyl-phen-yl)imino]-meth-yl}-4-nitro-phenol-2-{(E)-[(4-methyl-phen-yl)iminio]meth-yl}-4-nitro-phenolate (0.60/0.40).

Project description:The crystal of the title compound, 0.6C(14)H(12)N(2)O(3)·0.4C(14)H(12)N(2)O(3), contains a mixture of its neutral (OH containing) and zwitterionic (NH containing) forms, in a 0.60?(4):0.40?(4) ratio. The former generates an S(6) loop via an intra-molecular O-H?N hydrogen bond and the latter generates an S(6) loop via an N-H?O hydro-gren bond. The aromatic rings are oriented at a dihedral angle of 42.52?(10)°. In the crystal, C-H?? inter-actions occur and aromatic ?-? stacking inter-actions [centroid-centroid separations = 3.7106?(12) and 3.9177?(13)?Å] consolidate the packing.

| S-EPMC3200654 | biostudies-literature

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