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In the title thio­semicarbazone derivative, C9H10N4OS·H2O, intra­molecular N—H⋯N hydrogen bonds result in the formation of two nearly coplanar five- and six-membered rings, which are also almost coplanar with the adjacent phenyl ring. The oxime group has an E configuration and is involved in inter­molecular O—H⋯O hydrogen bonding as a donor. In the crystal structure, intra­molecular O—H⋯S and N—H⋯N and inter­molecular O—H⋯O and N—H⋯S hydrogen bonds generate edge-fused R 2 2(8) and R 4 1(11) ring motifs. The hydrogen-bonded motifs are linked to each other to form a three-dimensional supra­molecular network.

In the mol­ecule of the title compound, C18H16N4O, the intra­molecular N—H⋯N hydrogen bond results in the formation of a planar five-membered ring, which is also co-planar with the adjacent five-membered ring, being oriented at a dihedral angle of 1.23 (3)°. The dihedral angles formed by the planar pyrazole ring with the adjacent phenyl ring and the other phenyl ring are 7.29 and 11.21°, respectively. The dihedral angle between the two phenyl rings is 18.07°. In the crystal structure, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules.

The mol­ecule of the title compound, C10H11N3O3, adopts an all-trans conformation and is approxomately planar, the largest deviation from the least-squares plane through all non-H atoms being 0.261 (1) Å. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, the mol­ecules are packed into layers lying parallel to the ab plane by π-stacking inter­actions between the benzene ring of one molecule and the C—N bond of the oxime group of another molecule; the shortest inter­molecular C⋯C separation within the layer is 3.412 (1) Å. The layers are connected by O—H⋯O and N—H⋯O hydrogen bonds.

In the crystal structure of the title compound, C18H12N2OS, centrosymmetric dimers are stabilized both by van der Waals inter­actions and by two types of inter­molecular O—H⋯N hydrogen bonds. In addition, an intra­molecular C—H⋯S hydrogen bond is observed. The dihedral angles between the central ring and the two pendant phenyl rings are 7.4 (1) and 45.06 (9)°.

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 mol­ecule, C16H13NO, the indoline-2-one ring system is nearly planar [maximum atomic deviation = 0.082 (2) Å] and is oriented at a dihedral angle of 66.60 (12)° with respect to the phenyl ring. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into supra­molecular dimers.

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.

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 neutral, mononuclear title complex, [Ni(C4H6NO3)2(H2O)2], the Ni atom lies on a crystallographic inversion centre within a distorted octa­hedral N2O4 environment. Two trans-disposed anions of 3-hydroxy­imino­butanoic acid occupy four equatorial sites, coordinated by the deprotonated carboxyl­ate and protonated oxime groups and forming six-membered chelate rings, while the two axial positions are occupied by the water O atoms. The O atom of the oxime group forms an intra­molecular hydrogen bond with the coordinated carboxyl­ate O atom. The complex mol­ecules are linked into chains along b by hydrogen bonds between the water O atom and the carboxyl­ate O of a neighbouring mol­ecule. The chains are linked by further hydrogen bonds into a layer structure.

The title compound, C10H12N4O2, features an intra­molecular N—H⋯N hydrogen bond formed between the imine NH and oxime N atoms. The oxime group and the amide C=O bond are anti to each other. In the crystal, mol­ecules are connected by O—H⋯O hydrogen bonds into supra­molecular zigzag chains along the c axis.

In the title compound, C9H11N3O·CH4O, the semicarbazone moiety is nearly planar [maximum deviation = 0.017 (2) Å] and is twisted by a dihedral angle of 29.40 (13)° with respect to the phenyl ring. The semicarbazone moiety and phenyl ring are located on opposite sides of the C=N bond, showing the E configuration. An inter­molecular O—H⋯O and N—H⋯O hydrogen-bonding network occurs in the crystal structure.

Two independent mol­ecules are present in the asymmetric unit of the title compound, C12H11ClN4, (Z′ = 2): the dihedral angles between the phenyl and pyridizine rings are 8.35 (10) and 37.64 (6)°. In the crystal, the two mol­ecules form inversion dimers with R 2 2(8) ring motifs through inter­molecular N—H⋯N hydrogen bonds. The crystal structure is stabilized by π–π inter­actions between the pyridazine rings of symmetry-related molecules. In one of the independent mol­ecules, the centroid–centroid separations are 3.6927 (13) and 3.7961 (13) Å, whereas in the other, the separations are 3.6909 (13) and 3.9059 (13) Å.

The Ni atom of the title complex, [Ni(C8H8NO3)2]·2C3H7NO, lies on a center of inversion in a square-planar N2O2 coordination environment. An intra­molecular O—H⋯O hydrogen bond exists between the oximic hydr­oxy group of one ligand and the metal-coordinated O atom of the symmetry-related ligand. The dimethyl­formamide solvent mol­ecules are connected to the phenolate groups of the complex via O—H⋯O hydrogen bonds.

In the title compound, C20H21NO4, the two benzene rings are almost perpendicular to each other, making a dihedral angle of 86.1 (7)°. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hy­droxy­ethanimine [C=N—OH] group being 0.011 (1) Å for the O atom. An intra­molecular C—H⋯O hydrogen bond occurs. The mol­ecules are linked into cyclic centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds. Inter­molecular C—H⋯O hydrogen bonds link the mol­ecules, forming a C(8) chain along the a axis. The crystal packing is further stabilized by C—H⋯π inter­actions.

The title compound, C15H13ClN2O2, adopts an E conformation with respect to the azomethine C=N bond. The aniline and phenol rings are almost coplanar, making a dihedral angle of 3.33 (2)°. In the crystal, the mol­ecules lie about inversion centers, forming dimers that are connected by inter­molecular O—H⋯N hydrogen bonds, resulting in six-membered rings with graph-set motif R 2 2(6). In addition, there is a strong inter­molecular O—H⋯N hydrogen-bonding inter­action, resulting in an S(6) ring motif. Weak π–π inter­actions between the benzene rings [centroid–centroid distance = 3.809 (1) Å] further 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 title compound, C6H12N4OS, an intra­molecular N—H⋯N hydrogen-bond is present giving rise to an S(5) ring motif. In the crystal, double-stranded chains propagating along [10] are formed via pairs of O—H⋯S and N—H⋯S hydrogen bonds. The chains are further stabilized by C—H⋯S interactions.

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.

The mol­ecule of the title compound, C5H9NO3, is essentially planar [the maximum deviation for a non-H atom from the mean plane is 0.021 (3) Å] due to the π-conjugation of the hydroxy­imino and carbonyl groups, which are trans to each other; ab initio calculations in vacuo at the DFT (B3LYP/6–311G**++) level of theory confirmed that E conformer is indeed the lowest in energy. The packing in crystal structure is influenced by strong inter­molecular O—H⋯N hydrogen-bonding inter­actions between oxime groups and also by π-stacking of the mol­ecules due to the carbonyl and oxime group orbital overlap [inter­planar distance between adjacent mol­ecules = 3.143 (4) Å]. Jointly, these factors afford infinite 6.32 Å thick mol­ecular sheets, where the plane of each mol­ecule is perpendicular to the plane of the sheet. Seen from above, the mol­ecules within the sheet are arranged in a herringbone pattern. Such sheets form a stack due to weak van der Waals inter­actions; the gap between adjacent sheets is 2.07 Å.

The title centrosymmetric mononuclear complex, [Ni(C4H6NO3)2(H2O)2], is a polymorph of the previously reported complex [Dudarenko et al. (2010 ▶). Acta Cryst. E66, m277–m278]. The NiII atom, lying on an inversion center, is six-coordinated by two carboxyl­ate O atoms and two oxime N atoms from two trans-disposed chelating 3-hydroxy­imino­butanoate ligands and two axial water mol­ecules in a distorted octa­hedral geometry. The hydr­oxy group forms an intra­molecular hydrogen bond with the coordinated carboxyl­ate O atom. The complex mol­ecules are linked in stacks along [010] by a hydrogen bond between the water O atom and the carboxyl­ate O atom of a neighboring mol­ecule. The stacks are further linked by O—H⋯O hydrogen bonds into a layer parallel to (001).

In the title compound, C14H9NO2, a static disorder exists between the keto–oxime and hy­droxy–nitroso tautomers, in an approximate ratio of 4.6:1, based on refined occupancies for disordered parts. No inter­molecular hydrogen bonding is present in the crystal structure. Instead, both tautomers exhibit similar intra­molecular O—H⋯O hydrogen bonds.

The title compound, C16H13Cl2F3N2, exists in an E conformation with respect to the C=N bond [1.2952 (11) Å] and the C—N—N=C torsion angle is 175.65 (8)°. The dihedral angle between the benzene rings is 42.09 (4)°. An intra­molecular C—H⋯F hydrogen bond generates an S(6) ring. In the crystal, the mol­ecules are linked into [101] chains by C—H⋯F hydrogen bonds.

In the title compound, [Fe(C9H13N4O4)(NH3)2], the FeIII atom, lying on a mirror plane, is coordinated by four N atoms of a triply deprotonated tetra­dentate N-[2-(hy­droxy­imino)­propion­yl]-N′-[2-(oxidoimino)­propion­yl]propane-1,3-diaminide ligand in the equatorial plane and two N atoms of two ammonia mol­ecules at the axial positions in a distorted octa­hedral geometry. A short intra­molecular O—H⋯O hydrogen bond between the cis-disposed oxime O atoms stabilizes the pseudo-macrocyclic configuration of the ligand. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into a three-dimensional network. The ligand has a mirror-plane symmetry. One of the methyl­ene groups of the propane bridge is disordered over two sets of sites with equal occupancy factors.

In the title mol­ecule, C17H18N4O, the two phenyl rings form a dihedral angle of 18.15 (17)°. In the crystal, pairs of inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers. Weak inter­molecular C—H⋯O inter­actions further link the dimers into chains running along [010].

In the mol­ecule of the title compound, C18H18N2O5S·H2O, the heterocyclic ring adopts a twisted conformation, while the aromatic rings are oriented at a dihedral angle of 45.46 (3)°. Intra­molecular C—H⋯O and N—H⋯O inter­actions result in the formations of planar five- and six-membered rings. In the crystal structure, N—H⋯O hydrogen bonds link the NH2 and SO2 groups through R 2 2(8) ring motifs, while C—H⋯O and N—H⋯O hydrogen bonds result in the formation of R 2 1(7) ring motifs. N—H⋯O and O—H⋯O hydrogen bonds link the uncoordinated water mol­ecules, forming a polymeric network. A weak C—H⋯π inter­action is also present.