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(E)-3-{[(2-Bromo-3-methyl-phen-yl)imino]-meth-yl}benzene-1,2-diol: crystal structure and Hirshfeld surface analysis.

ABSTRACT: The title compound, C₁₄H₁₂BrNO₂, was synthesized by the condensation reaction of 2,3-di-hydroxy-benzaldehyde and 2-bromo-3-methyl-aniline. It crystallizes in the centrosymmetric triclinic space group P . The configuration about the C=N bond is E. The dihedral angle between the planes of the 5-(2-bromo-3-methyl-phenyl ring and the catechol ring is 2.80 (17)°. In the crystal, O-H⋯O hydrogen-bond inter-actions consolidate the crystal packing.

SUBMITTER: Dogan OE

PROVIDER: S-EPMC6895958 | biostudies-literature |

REPOSITORIES: biostudies-literature

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3-[(E)-(4-Ethyl-phen-yl)imino-meth-yl]benzene-1,2-diol.

Project description:The title compound, C(15)H(15)NO(2), adopts the enol-imine tautomeric form. The dihedral angle between the two benzene rings is 48.1?(1)°. Intra-molecular O-H?N and O-H?O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. In the crystal, mol-ecules are linked into centrosymmetric R(2) (2)(10) dimers via pairs of O-H?O hydrogen bonds and the dimers may interact through very weak by ?-? inter-actions [centroid-centroid distance = 4.150?(1)?Å]. The ethyl group is disordered over two orientations, with occupancies of 0.587?(11) and 0.413?(11).

| S-EPMC2977215 | biostudies-literature

(E)-3-[(4-Butyl-phen-yl)imino-meth-yl]benzene-1,2-diol.

Project description:The title compound, C(17)H(19)NO(2), exists as an enol-imine tautomer. The dihedral angle between the two benzene rings is 4.6?(2)°. The mol-ecular structure is stabilized by intramol-ecular O-H?O and O-H?N hydrogen bonds which generate S(5) and S(6) ring motifs, respectively. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of O-H?O hydrogen bonds. In addition, C-H?? inter-actions involving both benzene rings are observed.

| S-EPMC2977352 | biostudies-literature

(<i>Z</i>)-3-({[3-Meth-oxy-5-(tri-fluoro-meth-yl)phen-yl]imino}meth-yl)benzene-1,2-diol.

Project description:The title compound, C15H12F3NO3, crystallizes with one mol-ecule in the asymmetric unit. The mean planes of the two phenyl rings of the Schiff base moiety, bearing the OH groups and the imine group, respectively, are inclined to each other by 4.91?(1)°. In the crystal, mol-ecules are linked via pairs of bifurcated O-H?O hydrogen bonds between the phenol OH groups, forming inversion dimers with an R 1 2(5) ring motif. The structure exhibits also intra-molecular O-H?N and C-H?F hydrogen-bonding inter-actions. Hirshfeld surfaces analysis and two-dimensional fingerprint plots were applied to qu-antify the inter-molecular inter-actions. The three F atoms of the tri-fluoro-methyl group are disordered over two sets of sites, with occupancy factors of 0.578?(8) and 0.422?(8). The crystal studied was refined as an inversion twin.

| S-EPMC6509687 | biostudies-literature

Crystal structure of 3-{(E)-[(3,4-di-chloro-phen-yl)imino]-meth-yl}benzene-1,2-diol.

Project description:In the title Schiff base, C13H9Cl2NO2, which arose from the condensation of 3,4-di-chloro-aniline with 2,3-di-hydroxy-benzaldehyde, the dihedral angle between the aromatic rings is 44.74?(13)°. Intra-molecular O-H?O and O-H?N hydrogen bonds close S(5) and S(6) rings, respectively. In the crystal, inversion dimers linked by pairs of O-H?O hydrogen bonds generate R 2 (2)(10) loops. A weak C-H?? inter-action is also observed.

| S-EPMC4384559 | biostudies-literature

(E)-2-[(2,4-Dichloro-phen-yl)imino-meth-yl]benzene-1,4-diol monohydrate.

Project description:The title compound, C(13)H(9)Cl(2)NO(2)·H(2)O, represents a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The mol-ecule is approximately planar (r.m.s. deviation 0.0818?Å), and the dihedral angle between the two aromatic rings is 7.46?(12)°. An O-H?N inter-action generates an S(6) ring. In the crystal, mol-ecules are linked by inter-molecular O-H?O hydrogen bonds involving the solvent water mol-ecule, forming chains.

| S-EPMC2972111 | biostudies-literature

2-[(2-Bromo-phen-yl)imino-meth-yl]-6-methyl-phenol.

Project description:In the title compound, C(14)H(12)BrNO, is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The dihedral angle between the two aromatic rings is 34.26?(9)° and an intra-molecular O-H?N hydrogen bond generates an S(6) ring.

| S-EPMC3009115 | biostudies-literature

(E)-3-[(3-Bromo-phen-yl)imino-meth-yl]benzene-1,2-diol: a combined X-ray and computational structural study.

Project description:The title compound, C(13)H(10)BrNO(2), exists as an enol-imine form in the crystal and adopts an E configuration with respect to the C=N double bond. The mol-ecule is close to planar, with a dihedral angle of 6.88?(14)° between the aromatic rings. Intra-molecular O-H?N and O-H?O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. The crystal structure is stabilized by inter-molecular O-H?O hydrogen-bond inter-actions, forming R(2) (2)(10) and R(2) (2)(20) chains along [100]. ab initio Hartree-Fock (HF), density-functional theory (DFT) and semi-empirical (AM1 and PM3) calculations and full-geometry optimizations were also performed. Although there are some discrepancies between the experimental and calculated parameters, caused presumably by the O-H?O hydrogen-bond inter-actions, there is an acceptable general agreement between them.

| S-EPMC2970385 | biostudies-other

(E)-2-[3-(Trifluoro-meth-yl)phenyl-imino-meth-yl]benzene-1,4-diol.

Project description:In the title compound, C(14)H(10)F(3)NO(2), the two benzene rings are oriented at a dihedral angle of 31.94?(14)°. An intra-molecular O-H?N hydrogen bond helps to stabilize the mol-ecular structure. In the crystal, inter-molecular O-H?O hydrogen bonding links the mol-ecules, forming chains running along the crystallographic a axis. The F atoms of the trifluoro-methyl group are disordered over two positions with refined site occupancies of 0.488?(5) and 0.512?(5).

| S-EPMC2971128 | biostudies-literature

4-Bromo-2-({4-[(hy-droxy-imino)-meth-yl]phen-yl}imino-meth-yl)phenol.

Project description:In the title compound, C(14)H(11)BrN(2)O(2), the mean planes of the two benzene rings are almost parallel to each other, making a dihedral angle of 4.09?(1)°. An intra-molecular O-H?N hydrogen bond occurs. In the crystal, inter-molecular O-H?N and C-H?O hydrogen bonds link the mol-ecules into a chain-like supra-molecular structure.

| S-EPMC3007216 | biostudies-literature

2-[(3-Bromo-phen-yl)imino-meth-yl]phenol.

Project description:The title compound, C(13)H(10)BrNO, was prepared by reaction of 3-bromo-aniline with 2-hydroxy-benzaldehyde at 377?K. The mol-ecular structure and packing are stabilized by an intra-molecular O-H?N hydrogen-bond inter-action.

| S-EPMC2960578 | biostudies-literature

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