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In the title compound, C20H21NO5, the dihedral angle between the mean planes through the two rings is 47.1 (8)°. The enoate group assumes an extended conformation. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.061 (1) Å for the O atom. In the crystal, mol­ecules are linked into cyclic centrosymmetric dimers with an R 2 2(6) motif via pairs of O—H⋯N hydrogen bonds. Inter­molecular C—H⋯O hydrogen bonds form a C(8) chain along the b axis. The crystal packing is further stabilized by C—H⋯π inter­actions.

In the title mononuclear cobalt(III) compound, [Co(C9H8ClNO2)(C9H9ClNO2)], the CoII atom is six-coordinated by two imine N atoms, two phenolate O atoms, and one hy­droxy and one oxide O atom from two Schiff base ligands, forming an octa­hedral geometry. In the crystal structure, adjacent mol­ecules are linked through inter­molecular O—H⋯O hydrogen bonds. The 2-oxidoethyl group is disordered over two positions in a 0.638 (3):0.362 (3) ratio.

The title Schiff base compound, C27H19ClN4O, features two intra­molecular O—H⋯N and N—H⋯N hydrogen bonds involving the hydr­oxy and amino groups to generate S(6) and S(5) ring motifs, respectively. In the crystal structure, weak inter­molecular N—H⋯O and C—H⋯N inter­actions, together with π–π contacts [centroid–centroid distances = 3.6294 (11)–3.6881 (11) Å], link neighboring mol­ecules.

In the title compound, C14H11BrN2O2, the mean planes of the two benzene rings are almost parallel to each other, making a dihedral angle of 4.09 (1)°. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, inter­molecular O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into a chain-like supra­molecular structure.

In the title compound, C15H13BrN2O2, he oxime unit adopts an E conformation with respect to the O—H group. A classical intra­molecular O—H⋯N hydrogen bond results in the formation of a six-membered ring. The crystal structure is stabilized by inter­molecular O—H⋯N hydrogen bonds between the hydr­oxy groups and the oxime N atoms. In addition, the crystal structure also features short inter­molecular Br⋯Br short contacts with a distance of 3.8768 (5) Å.

In the title compound, C22H22N4, the centroid of the benzene ring is located on an inversion centre. The dihedral angle between the benzene and pyridine rings is 10.94 (5)°. The crystal structure displays weak inter­molecular C—H⋯N hydrogen bonding and C—H⋯π inter­actions.

The title compound, C19H24N2O2, adopts the phenol–imine tautomeric form. An intra­molecular O—H⋯N hydrogen bond results in the formation of a six-membered ring. The aromatic rings are oriented at a dihedral angle of 17.33 (16)°. Inter­molecular C—H⋯π inter­actions occur in the crystal.

In the title compound, C16H16N2O3·H2O, the benzene rings are nearly coplanar with each other, forming a dihedral angle of 4.46 (3)°. There is a strong intra­molecular O—H⋯N hydrogen bond which results in a six-membered ring. In the crystal, the mol­ecules are connected into a three-dimensional network via O—H⋯O and O—H⋯N inter­molecular hydrogen bonds, forming a centrosymmetric ring along the b axis with graph-set motif R 4 4(10). In addition, the short distances between the centroids of six-membered rings [3.555 (1) Å], indicate the existence of π–π stacking inter­actions, which may stabilize the crystal structure.

The title compound, C13H16N2O3, adopts an E configuration with respect to the C=N bond and an intra­molecular N—H⋯N hydrogen bond results in the formation of a six-membered ring. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into a chain propagating along the b axis. Very weak π–π stacking inter­actions [centroid–centroid distance = 4.18 (2) Å] may further consolidate the packing, forming a two-dimensional supra­molecular network.

In the asymmetric unit of the title compound, C17H19NO3, there are three independent mol­ecules, which are align nearly parallel to each other and adopt the phenol-imine tautomeric form. In each mol­ecule, an intra­molecular O—H⋯N hydrogen bond results in the formation of an S(6) ring motif. The dihedral angles between the aromatic rings in the three independent mol­ecules are 13.55 (2), 21.24 (2) and 46.26 (1)°. C—H⋯π inter­actions are also observed in the crystal structure.

The title compound, C13H9Cl2NO, was crystallized from a methanol solution of 5-chloro­salicylaldehyde and o-chloro­aniline. The mol­ecule displays a trans configuration with respect to the imine C=N double bond. The N atom is involved in an intra­molecular O—H⋯N hydrogen bond. The two aromatic rings are essentially coplanar, the dihedral angle between them being 7.1 (1)°. A C—H⋯π inter­action is present in the crystal.

In the title compound, C18H16ClNO4, the dihedral angle between the mean planes through the aromatic rings is 83.8 (8)°. The hy­droxy­ethanimine group is essentially coplanar with the ring to which it is attached [O—N—C—C torsion angle = −177.96 (13)°]. The mol­ecules are linked into centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds. The crystal packing is further stabilized by C—H⋯O inter­actions.

In the title compound, C17H18BrClN2O, the dihedral angle between the aromatic rings is 3.0 (1)°. The methyl­ethanamine group assumes an extended conformation. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C—H⋯π and π–π [centroid–centroid distances = 3.691 (1) and 3.632 (1) Å] inter­actions.

The title mononuclear nickel(II) complex, [Ni(C9H9ClNO2)2]·H2O, was obtained by the reaction of 5-chloro­salicyl­aldehyde, 2-amino­ethanol and nickel nitrate in methanol. The Ni atom is six-coordinated by two phenolate O, two imine N and two hy­droxy O atoms from two crystallographically different Schiff base ligands, forming an octa­hedral geometry. In the crystal, mol­ecules are linked through inter­molecular O—H⋯O and O—H⋯Cl hydrogen bonds.

In the title compound, C13H9BrClNO, the dihedral angle between the substituted benzene rings is 43.90 (11)°. Strong intra­molecular O—H⋯N hydrogen bonds generate S(6) ring motifs. The crystal structure features short intemolecular Br⋯Br [3.554 (2) Å] and Cl⋯Cl [3.412 (2) Å] contacts. The crystal packing is further stabilized by inter­molecular C—H⋯O and C—H⋯π inter­actions.

The title compound, C13H8BrCl2NO, was obtained by reaction of 3-bromo-5-chloro­salicylaldehyde and 2-chloro­benzenamine in methanol. The mol­ecule displays an E configuration with respect to the imine C=N double bond. The dihedral angle between the two benzene rings is 4.57 (11)°. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond. In the crystal structure, mol­ecules are linked by inter­molecular C—H⋯O hydrogen-bonding inter­actions into zigzag chains running parallel to the b axis. Inter­molecular Br⋯Cl [3.5289 (11) Å] and Cl⋯Cl [3.5042 (12) Å] inter­actions are present.

The title compound, C8H7ClN2O2, is an inter­mediate in the synthesis of 5-chloro­isatin, which can be further transformed to 5-chloro-2-indolinone via a Wolff–Kishne reduction. The C2N acetamide plane forms a dihedral angle of 6.3 (3)° with the benzene ring. An intra­molecular C—H⋯O inter­action results in the formation of a six-membered ring. In the crystal, inter­molecular N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonds link the mol­ecules into multimers, forming sheets.

In the title compound, C21H18N2O, the dihedral angle between the phenol ring and the carbazole system is 39.34 (2)°. Inter­molecular O—H⋯N hydrogen bonds and C—H⋯π and π–π inter­actions [centroid–centroid distances = 3.426 (2) and 3.768 (2) Å] stabilize the crystal structure.

The title compound, C27H19BrN4O, is a mono-anil Schiff base ligand. Three intra­molecular O—H⋯N and N—H⋯N hydrogen bonds involving the hydr­oxy and amino groups generate S(6) and S(5) ring motifs, respectively. In the crystal structure, weak inter­molecular N—H⋯O and C—H⋯O hydrogen bonds together with π–π inter­actions [centroid–centroid distances = 3.628 (3)–3.729 (3) Å] link neighboring mol­ecules.

The title compound, C14H9ClF3NO2, crystallizes in a phenol–imine tautomeric form, with a strong intra­molecular O—H⋯N hydrogen bond. The dihedral angle between the two benzene rings is 47.62 (9)°. In the crystal, mol­ecules are linked into chains along the c axis by C—H⋯O hydrogen bonds, and weak C—H⋯π inter­actions involving both benzene rings are also observed.

The title compound, C14H14N2O, exists as the enol–imine tautomer. A strong intra­molecular hydrogen bond between O and N atoms forms a six-membered ring with an S(6) graph-set motif, which is approximately coplanar with the phenol ring, the inter­planar angle being 3.4 (3)°. In the crystal, inter­molecular C—H⋯O hydrogen bonds and N—H⋯π inter­actions link the mol­ecules into infinite chains along [100].

In the title compound, C27H27N7O9·CH3CN, the three nitro groups of the polydentate tripodal Schiff base are located approximately parallel to their respective carrier benzene rings, making dihedral angles of 3.9 (4), 5.0 (4) and 6.3 (4)°. Intra­molecular O—H⋯N hydrogen bonds between the hy­droxy O atoms and the imine N atoms, with O⋯N distances in the range 2.607 (3)–2.665 (3) Å, form nearly planar six-membered rings. In the crystal, weak inter­molecular C—H⋯O and C—H⋯N hydrogen bonds occur and several intra- and inter­molecular π–π inter­actions are present between adjacent benzene rings, with a shortest centroid–centroid distance of 3.507 (2) Å.

In the crystal of the centrosymmetric title compound, C20H20N2S2, mol­ecules are linked by head-to-tail C—H⋯N hydrogen bonds, resulting in chains extending along the a axis. Three additional C—H⋯π inter­molecular inter­actions give rise to a herringbone packing motif which extends along the c axis. The C—H⋯N inter­actions provide links between the sheets.

The title compound, C13H10ClNO2, exists in the phenol–imine form in the crystal, and the aromatic rings are oriented at a dihedral angle of 2.82 (9)°. An intra­molecular O—H⋯N hydrogen bond results in the formation of a planar six-membered ring. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains.

In the title compound, [CdCl2(C13H19N3O)], the CdII ion is penta­coordinated with the N,N,O-tridentate Schiff base 2-{[2-(piperazin-4-ium-1-yl)eth­yl]imino­meth­yl}phenolate ligand and two Cl atoms in a highly distorted square-pyramidal geometry; the piperazine ring adopts a chair conformation. In the crystal structure, adjacent mol­ecules are linked together via N—H⋯O and N—H⋯Cl hydrogen bonds, forming infinite layers parallel to the ab plane. The layers are further connected through C—H⋯Cl inter­actions into a three-dimensional network.