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(E)-4-Meth-oxy-2-(p-tolyl-imino-meth-yl)phenol.

ABSTRACT: The mol-ecule of the title compound, C(15)H(15)NO(2), adopts the enol-imine tautomeric form and has a strong intra-molecular O-H⋯N hydrogen bond as a result. The mol-ecule is almost planar, with a maximum deviation of 0.1038 (15) Å for the meth-oxy C atom. A weak C-H⋯π inter-action and a weak C-H⋯O hydrogen bond are present in the crystal.

SUBMITTER: Kosar B

PROVIDER: S-EPMC2979976 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(E)-5-Meth-oxy-2-(o-tolyl-imino-meth-yl)phenol.

Project description:In the title compound, C(15)H(15)NO(2), the phenol group make dihedral angles of 2.4?(2) and 24.1?(9)° with the imine linkage (-C=N-) and the phenyl group, respectively, and the mol-ecule adopts the enol-imine tautomeric form, so the mol-ecular structure is stabilized by a strong intra-molecular O-H?N hydrogen bond. The crystal structure features a weak C-H?? inter-action.

| S-EPMC2979691 | biostudies-literature

(E)-4-Meth-oxy-2-(o-tolyl-imino-meth-yl)phenol.

Project description:In the mol-ecule of the title compound, C(15)H(15)NO(2), the aromatic rings are oriented at a dihedral angle of 15.46 (6)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a nearly planar six-membered ring [maximum deviation of 0.035 (5) Å for the N atom] which is almost coplanar with the adjacent ring, making a dihedral angle of 0.8 (3)°. The title organic mol-ecule is a phenol-imine tautomer, as evidenced by the C-O, C-N and C-C bond lengths. Mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds that generate a C(5) chain. C-H⋯π and π-π inter-actions exist in the structure. The π-π inter-action occurs between the phenol ring and its symmetry equivalent at (1 - x, 1 - y, -z), with a centroid-centroid distance of 3.727 (7) Å and a plane-to-plane separation of 3.383 (5) Å, resulting in an offset angle of 24.82 (1)°.

| S-EPMC2968945 | biostudies-literature

2-(m-Tolyl-imino-meth-yl)phenol.

Project description:The title compound, C(14)H(13)NO, is non-planar with a dihedral angle of 47.00?(6)° between the planes of the two aromatic rings. Intra-molecular hydrogen bonding is observed between the O-H group and the N atom, resulting in a phenol-imine tautomeric form.

| S-EPMC2972180 | 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

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

Project description:The title compound, C(15)H(15)NO(3), adopts the enol-imine tautomeric form. The two rings are twisted with respect to each other, making a dihedral angle of 44.08 (5)°. The 3-methoxy-2-[(E)-(4-methoxyphenyl)-iminomethyl]phenol unit is almost planar, the largest deviation from the mean plane being 0.047 (2) Å. Such a planar conformation might be related to the occurrence of an intra-molecular O-H⋯N hydrogen bond. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into sheets parallel to (010). These sheets are inter-connected by weak C-H⋯π inter-actions.

| S-EPMC3051687 | biostudies-literature

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

Project description:In the mol-ecule of the title compound, C(14)H(13)NO(2), the two aromatic rings are oriented at a dihedral angle of 0.78?(20)°; with the exception of two methyl H atoms the mol-ecule is essentially planar. The intra-molecular O-H?N hydrogen bond results in the formation of a non-planar, six-membered ring, which adopts a flattened-boat conformation. In the crystal structure, inter-molecular C-H?O hydrogen bonds link the mol-ecules to form parallel networks. There is a C-H?? contact between the methyl group and the benzene ring. A ?-? contact between the benzene and phenyl rings [centroid-centroid distance = 4.681?(5)?Å] is also observed.

| S-EPMC2960573 | biostudies-literature

6-Meth-oxy-2-[(E)-phenyl-imino-meth-yl]phenol.

Project description:The title compound, C(14)H(13)NO(2), was obtained by the condensation reaction of o-vanillin and aniline in ethanol. The mol-ecule adopts the phenol-imine tautomeric form and an E conformation with respect to the azomethine C=N bond. The dihedral angle between the aromatic rings is 30.57?(10)°. In the crystal, mol-ecules are linked by inter-molecular C-H?O hydrogen bonds into zigzag chains parallel to the b axis.

| S-EPMC3099786 | 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 ?-? 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

5-Bromo-2-meth-oxy-4-{[(4-meth-oxy-phen-yl)imino]-meth-yl}phenol monohydrate.

Project description:The crystal structure of the title compound, C(15)H(14)BrNO(3)·H(2)O, has a trans configuration about the central C=N double bond. An intra-molecular O-H⋯O hydrogen bond occurs in the main mol-ecule. The crystal packing is stabilized by strong O-H⋯O and O-H⋯N hydrogen bonds.

| S-EPMC3274944 | biostudies-literature

2-Eth-oxy-6-[(methyl-imino)-meth-yl]phenol.

Project description:In the title compound, C(10)H(13)NO(2), synthesized by the reaction of 2-hy-droxy-3-eth-oxy-benzaldehyde with methyl-amine, there is an an intra-molecular O-H?N hydrogen bond involving the hy-droxy substituent and the amino N atom. In the crystal, mol-ecules form inversion dimers connected by pairs of C-H?O hydrogen bonds.

| S-EPMC3006704 | biostudies-literature

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