<i>N</i>′-[(<i>E</i>)-2-Hydroxy-5-methoxybenzylidene]pyridine-4-carbohydrazide monohydrate

Prasanna, M.K.; Sithambaresan, M.; Pradeepkumar, K.; Kurup, M.R. Prathapachandra

doi:10.1107/s160053681301235x

Cited by 6 publications

(4 citation statements)

References 9 publications

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“…Hence, compounds (I) and (II) are in the keto tautomeric form, which can be verified from the C O and C-NH bond lengths of the amide unit: O1 C6 [1.230 (2) Å for (I) and 1.223 (2) Å for (II)] and N2-C6 [1.351 (2) Å for (I) and 1.355 (2) Å for (II)]. The bond distances C7 N3 [1.282 (2) Å for (I) and 1.278 (2) Å for (II)] and C6 O1 [1.229 (2) Å for (I) and 1.220 (2) Å for (II)], are very close to the recognized double C N and C O bond lengths (Prasanna et al, 2013;Wang et al, 2010), confirming that the carbohydrazide exists as an amido tautomer in the solid state. In the two compounds, the three bond angles around atom C6 (see Tables 1 and 2) differ from 120 , probably in order to decrease the repulsion between the lone pairs present on atoms N2 and O1.…”

Section: Figuresupporting

confidence: 52%

The crystal structures and Hirshfeld surface analysis of N′,N′′′-((1E,1′E)-{[methylenebis(oxy)]bis(6-bromo-3,1-phenylene)}bis(methanylylidene))bis(isonicotinohydrazide) dihydrate and N′,N′′′-((1E,1′E)-{[butane-1,4-diylbis(oxy)]bis(2,1-phenylene)}bis(methanylylidene))bis(isonicotinohydrazide) [+ solvent]

Abuthahir¹,

NizamMohideen²,

Viswanathan

et al. 2019

Acta Cryst E

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The title compounds, C27H20Br2N6O4·2H2O, (I), and C30H28N6O4·[+ solvent], (II), both crystallize with one half-molecule in the asymmetric unit. The whole molecule of (I) is generated by twofold rotation symmetry, with the twofold rotation axis bisecting the C atom of the –O—CH2—O– bridge. This results in a folded or U-shaped conformation of the molecule. The whole molecule of (II) is generated by inversion symmetry, with the central CH2—CH2 bond of the –O—(CH2)4—O– bridge being located about a center of inversion. This results in a step-like conformation of the molecule. The central C(=O)N—N=C regions of the isonicotinohydrazide moieties in both compounds are planar and the configuration about the imine C=N bonds is E. In compound (I), the benzene and pyridine rings are inclined to each other by 37.60 (6)°. The two symmetry-related pyridine rings are inclined to each other by 74.24 (6)°, and the two symmetry-related benzene rings by 7.69 (6)°. In compound (II), the benzene and pyridine rings are inclined to each other by 25.56 (11)°. The symmetry-related pyridine rings are parallel, as are the two symmetry-related benzene rings. In the crystal of (I), a pair of water molecules link the organic molecules via Owater—H...O and Owater—H...N hydrogen bonds, forming chains along [001], and enclosing an R 4 2(8) and two R 1 2(5) ring motifs. The chains are linked by N—H...Npyridine hydrogen bonds, forming a supramolecular framework. There are also a number of C—H...O hydrogen bonds, and C—H...π and offset π–π interactions [interplanar distance = 3.294 (1) Å] present reinforcing the framework. In the crystal of (II), molecules are linked by N—H...Npyridine hydrogen bonds, forming a supramolecular framework. Here too there are also a number of C—H...O hydrogen bonds present, and a C—H...π interaction, reinforcing the framework. For compound (II), a region of disordered electron density was corrected for using the SQUEEZE [Spek (2015). Acta Cryst. C71, 9–18] routine in PLATON. Their formula mass and unit-cell characteristics were not taken into account during refinement.

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Section: Figuresupporting

confidence: 52%

The crystal structures and Hirshfeld surface analysis of N′,N′′′-((1E,1′E)-{[methylenebis(oxy)]bis(6-bromo-3,1-phenylene)}bis(methanylylidene))bis(isonicotinohydrazide) dihydrate and N′,N′′′-((1E,1′E)-{[butane-1,4-diylbis(oxy)]bis(2,1-phenylene)}bis(methanylylidene))bis(isonicotinohydrazide) [+ solvent]

Abuthahir¹,

NizamMohideen²,

Viswanathan

et al. 2019

Acta Cryst E

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“…The crystal structures of H 2 L 1 and H 2 L 1 •H 2 O were reported previously [37,38]. Ligands H 2 L 3 and H 2 L 4 crystallize in orthorhombic Pna21 and triclinic P-1 space groups, respectively (Figure 1a, Supplementary Materials, Figure S1, Table S1).…”

Section: Hydrazonesmentioning

confidence: 57%

Preparative and Catalytic Properties of MoVI Mononuclear and Metallosupramolecular Coordination Assemblies Bearing Hydrazonato Ligands

Mandarić,

Topić,

Agustin

et al. 2024

IJMS

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A series of polynuclear, dinuclear, and mononuclear Mo(VI) complexes were synthesized with the hydrazonato ligands derived from 5-methoxysalicylaldehyde and the corresponding hydrazides (isonicotinic hydrazide (H2L1), nicotinic hydrazide (H2L2), 2-aminobenzhydrazide (H2L3), or 4-aminobenzhydrazide (H2L4)). The metallosupramolecular compounds obtained from non-coordinating solvents, [MoO2(L1,2)]n (1 and 2) and [MoO2(L3,4)]2 (3 and 4), formed infinite structures and metallacycles, respectively. By blocking two coordination sites with cis-dioxo ligands, the molybdenum centers have three coordination sites occupied by the ONO donor atoms from the rigid hydrazone ligands and one by the N atom of pyridyl or amine-functionalized ligand subcomponents from the neighboring Mo building units. The reaction in methanol afforded the mononuclear analogs [MoO2(L1-4)(MeOH)] (1a–4a) with additional monodentate MeOH ligands. All isolated complexes were tested as catalysts for cyclooctene epoxidation using tert-butyl hydroperoxide (TBHP) as an oxidant in water. The impact of the structure and ligand lability on the catalytic efficiency in homogeneous cyclooctene epoxidation was elucidated based on theoretical considerations. Thus, dinuclear assemblies exhibited better catalytic activity than mononuclear or polynuclear complexes.

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“…The N2-N1-C5-O2 torsion angle of -0.1 (4)° indicates the cis configuration of the O2 atom with respect to the hydrazine nitrogen atom N2. The bond distances C6═N2 [1.275 (3) Å] and C5═O2 [1.224 (3) Å] are very close to the formal double C═N and C═O bond lengths (Prasanna, et al, 2013) The molecular structure of the title compound, showing the atomic numbering and displacement ellipsoids drawn at 30% probability level.…”

Section: Methodsmentioning

confidence: 87%

“…For the biological activity of hydrazones derived from isoniazid (systematic name: isonicotinohydrazide), see: Rollas & Kucukguzel (2007). For related structures, see: Prabhu et al (2011); Bikas et al (2010); Prasanna et al (2013). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

N′-[(E)-3-Bromo-5-chloro-2-hydroxybenzylidene]furan-2-carbohydrazide

2014

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In the title compound, C12H8BrClN2O3, the furan ring makes a dihedral angle of 17.2 (2)° with the six-membered ring. An intramolecular O–H⋯N hydrogen bond stabilizes the molecular conformation. In the crystal, N–H⋯O hydrogen bonds connect the molecules into chains running along the c-axis direction. The crystal packing is additionally stabilized by C—H⋯O interactions into a three-dimensional supramolecular architecture.

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N′-[(E)-2-Hydroxy-5-methoxybenzylidene]pyridine-4-carbohydrazide monohydrate

Cited by 6 publications

References 9 publications

Preparative and Catalytic Properties of MoVI Mononuclear and Metallosupramolecular Coordination Assemblies Bearing Hydrazonato Ligands

N′-[(E)-3-Bromo-5-chloro-2-hydroxybenzylidene]furan-2-carbohydrazide

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