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Crystal structure, Hirshfeld surface analysis and HOMO-LUMO analysis of (E)-N'-(3-hy-droxy-4-meth-oxy-benzyl-idene)nicotinohydrazide monohydrate.

ABSTRACT: The mol-ecule of the title Schiff base compound, C₁₄H₁₃N₃O₃·H₂O, displays a trans configuration with respect to the C=N bond. The dihedral angle between the benzene and pyridine rings is 29.63 (7)°. The crystal structure features inter-molecular N-H⋯O, C-H⋯O, O-H⋯O and O-H⋯N hydrogen-bonding inter-actions, leading to the formation of a supramolecular framework. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (37.0%), O⋯H/H⋯O (23.7%)), C⋯H/H⋯C (17.6%) and N⋯H/H⋯N (11.9%) inter-actions. The title compound has also been characterized by frontier mol-ecular orbital analysis.

SUBMITTER: Sivajeyanthi P

PROVIDER: S-EPMC6658940 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure of (E)-N'-(5-bromo-2-hy-droxy-benzyl-idene)nicotinohydrazide monohydrate.

Project description:In the title compound, C13H10BrN3O2·H2O, the conformation about the azomethine double bond is E. The mol-ecule exists in the amido form with a C=O bond length of 1.229 (2) Å. There is an intra-molecular O-H⋯N hydrogen bond forming an S(6) ring motif. The whole mol-ecule is almost planar, with an r.m.s. deviation of 0.021 Å for all non-H atoms, and the dihedral angle between the planes of the pyridine and benzene rings is 0.74 (12)°. In the crystal, the water mol-ecule of crystallization links the organic mol-ecules via Ow-H⋯O, Ow-H⋯N and N-H⋯Ow hydrogen bonds and short C-H⋯Ow contacts, forming sheets lying parallel to (100). Within the sheets there is a weak π-π inter-action involving the pyridine and benzene rings [centroid-to-centroid distance = 3.8473 (15) Å]. The sheets are linked via C-H⋯Br inter-actions, forming a three-dimensional network.

| S-EPMC4518959 | biostudies-literature

(E)-N'-(5-Bromo-2-hy-droxy-3-meth-oxy-benzyl-idene)-2-hy-droxy-benzohydrazide monohydrate.

Project description:The organic molecule of the title hydrate, C(15)H(13)BrN(2)O(4)·H(2)O, is roughly planar, with a mean deviation of 0.0939?(2)?Å. The dihedral angle between the two aromatic rings is 8.2?(3)°. Intra-molecular O-H?N and O-H?O hydrogen bonds are observed. In the crystal, N-H?O(water) and O(water)-H?O hydrogen bonds lead to a three-dimensional network.

| S-EPMC3393308 | biostudies-literature

(E)-N'-(3,4-Di-meth-oxy-benzyl-idene)nicotinohydrazide monohydrate.

Project description:In the title hydrated compound, C15H15N3O3·H2O, the nicotinohydrazide mol-ecule adopts a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene and pyridine rings is 5.10?(14)°. In the crystal, the solvent water mol-ecule acts as an acceptor, forming an N-H?O hydrogen bond supported by two C-H?O contacts. It also acts as a donor, forming bifurcated O-H?(O,O) and O-H?N hydrogen bonds that combine with the former contacts to form zigzag chains of mol-ecules along the c-axis direction. An additional O-H?O donor contact completes a set of six hydrogen bonds to and from the water mol-ecule and connects it to a third nicotinohydrazide mol-ecule. This latter contact combines with weaker C-H?O hydrogen bonds supported by a C-H?? contact to stack mol-ecules along b in a three-dimensional network.

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(E)-4-Amino-N'-(2-hy-droxy-5-meth-oxy-benzyl-idene)benzohydrazide monohydrate.

Project description:In the title compound, C(15)H(15)N(3)O(3)·H(2)O, the hydazide Schiff base mol-ecule shows an E conformation around the C=N bond. An intra-molecular O-H?N hydrogen bond makes an S(6) ring motif. The dihedral angle between the substituted phenyl rings is 23.40?(11)°. The water mol-ecule mediates linking of neighbouring mol-ecules through O-H?(O,O) hydrogen bonds into infinite chains along the a axis, which are further connected together through N-H?O hydrogen bonds, forming a two-dimensional network parallel to (001). C-H?O inter-actions aso occur.

| S-EPMC3414187 | biostudies-literature

(E)-4-Bromo-N'-(4-hy-droxy-3-meth-oxy-benzyl-idene)benzohydrazide monohydrate.

Project description:In the title compound, C(15)H(13)BrN(2)O(3)·H(2)O, the dihedral angle between the two benzene rings is 13.92?(6)°. The meth-oxy group of the 4-hy-droxy-3-meth-oxy-phenyl is almost coplanar with its bound benzene ring, as seen by the C(meth-yl)-O-C-C torsion angle of -0.35?(16)°. In the crystal, mol-ecules are linked into a three-dimensional network by N-H?O, O-H?N and O-H?O hydrogen bonds and also weak C-H?O inter-actions. A short C?O contact of 3.0191?(15)?Å is also present.

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N'-[(E)-5-Bromo-2-hy-droxy-3-meth-oxy-benzyl-idene]benzohydrazide monohydrate.

Project description:The title compound, C15H13BrN2O3·H2O, exists in an E conformation with respect to the azo-methane C=N double bond. The benzene and phenyl rings form dihedral angles of 0.46?(2) and 4.90?(3)°, respectively with the central C(=O)N2C unit. An intra-molecular O-H?N hydrogen bond occurs. In the crystal, some hydrazide mol-ecules are replaced by mol-ecules of the 6-bromo isomer. The Br atom from this admixture was refined to give a partial occupancy of 0.0443?(19). A supra-molecular network is built in the lattice by means of inter-molecular N-H?O and two O-H?O inter-actions together with non-classical C-H?O inter-actions involving the lattice water mol-ecule stacking the mol-ecules along the b-axis direction.

| S-EPMC3885046 | biostudies-literature

2-[(2-Hy-droxy-4-meth-oxy-benzyl-idene)aza-nium-yl]benzoate monohydrate.

Project description:In the title compound, C(15)H(13)NO(4)·H(2)O, the Schiff base exists in a zwitterionic form and a bifurcated intra-molecular N-H⋯(O,O) hydrogen bond generates two S(6) rings. The dihedral angle between the two benzene rings is 25.8 (2)°. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds.

| S-EPMC3006953 | biostudies-literature

N'-[(E)-2-Hy-droxy-5-meth-oxy-benzyl-idene]pyridine-4-carbohydrazide monohydrate.

Project description:The title compound, C14H13N3O3·H2O, adopts an E conformation with respect to the azomethine bond and crystallizes in the amide form. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, the lattice water molecule plays a major role in the supramolecular architecture by interconnecting adjacent molecules into a three-dimensional netwrok by means of O-H⋯O, O-H⋯N and N-H⋯O hydrogen-bonding inter-actions. The structure also features two non-classical C-H⋯O inter-actions.

| S-EPMC3685038 | biostudies-literature

(E)-N'-(3-Bromo-5-chloro-2-hy-droxy-benzyl-idene)nicotinohydrazide.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C(13)H(9)BrClN(3)O(2), in which the dihedral angles between the benzene and pyridine rings are 8.23?(9)° and 52.84?(12)°. Both the mol-ecules exist in an E configuration with respect to the C=N double bond. The two mol-ecules in the asymmetric unit are linked via weak C-H?O hydrogen bonds. In both the mol-ecules, an intra-molecular O-H?N hydrogen bond generate an S(6) graph-set motif. In the crystal, inter-molecular N-H?O and C-H?O hydrogen bonds generate bifurcated R(1) (2)(7) ring motifs. The crystal packing is further stabilized by weak inter-molecular N-H?O, N-H?N, C-H?O and ?-? [centroid-centroid distance 3.615?(2)?Å] inter-actions.

| S-EPMC3201283 | biostudies-literature

(E)-N'-(2-Hy-droxy-3,5-diiodo-benzyl-idene)nicotinohydrazide acetonitrile monosolvate.

Project description:In the hydrazone molecule of the title compound, C(13)H(9)I(2)N(3)O(2)·CH(3)CN, the aromatic rings form a dihedral angle of 9.4 (3)°. In the crystal structure, inter-molecular I⋯N inter-actions [3.099 (4) Å] link hydrogen-bonded aggregates of the hydrozone and solvent molecules related by translation along the b axis into chains. An intramolecular O-H⋯N hydrogen bond forms an S(6) ring.

| S-EPMC3151945 | biostudies-literature

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