Synthesis,crystal structures,and antimicrobial activity of copper(II) and zinc(II) complexes derived from 2-bromo-4-chloro-6-[(2-morpholin-4-ylethylimino)methyl]phenol

An end-to-end azido-bridged dinuclear copper(II) complex [Cu₂L₂(μ_1,3-N₃)](NO₃) (I) and a mononuclear zinc(II) complex [ZnCl₂(HL)] ? CH₃OH (II), where L is 2-brom-4-chloro-6-[(2-morpholin- 4-ylethylimino)methyl]phenolate, have been prepared and characterized by elemental analyses, IR, and single crystal X-ray crystallographic determination (CIF files CCDC nos. 1415217 (I), 1415218 for (II)). The crystal of I is monoclinic: space group C2/c, a = 28.684(2), b = 7.1787(5), c = 18.292(1) Å, β = 117.887(3)°, V = 3329.1(4) ų, Z = 4. The crystal of II is monoclinic: space group P2₁/c, a = 10.8207(9), b = 12.3398(7), c = 14.9477(7) Å, β = 93.473(3)°, V = 1992.2(2) ų, Z = 4. The Schiff base ligand in I coordinates to the Cu atom through the phenolate O, imine N, and morpholine N atoms, while the Schiff base ligand in II coordinates to the Zn atom through the phenolate O and imine N atoms, with the morpholine N atom protonated. The effect of these complexes on the antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Candida albicans was studied.     

Synthesis,crystal structures,and antibacterial activities of Schiff base zinc(II) complexes [Zn(L<Superscript>1</Superscript>)<Subscript>2</Subscript>] and [Zn(L<Superscript>2</Superscript>)<Subscript>2</Subscript>]

The reaction of cyclopentylamine with 2-hydroxy-1-naphthaldehyde and 5-nitrosalicylaldehyde, respectively, in methanol affords two new Schiff bases, 1-(cyclopentyliminomethyl)naphthalen-2-ol (HL¹) and 4-nitro-2-(cyclopentyliminomethyl)phenol (HL²). Two new zinc(II) complexes, [Zn(L¹)₂] (I) and [Zn(L²)₂] (II), derived from the Schiff bases, have been prepared and characterized by single-crystal X-ray diffraction, FT-IR, and elemental analysis. Complex I crystallizes in the monoclinic space group P2₁/c with a = 17.834(4), b = 14.738(3), c = 9.868(2) Å, β = 91.20(3)°, V = 2593.1(9) ų, Z = 4. Complex II crystallizes in the triclinic space group P \(\bar 1\) with a = 10.206(1), b = 10.502(1), c = 12.554(1) Å, α = 66.771(2)°, β = 78.133(2)°, γ = 76.292(2)°, V = 1191.8(1) ų, Z = 2. The Zn atom in each complex is coordinated by two N and two O atoms from two Schiff base ligands, forming a tetrahedral geometry. The Schiff bases and the complexes were assayed for antibacterial activities.     

Synthesis,characterization, and crystal structures of two Schiff base zinc(II) complexes with urease inhibitory activities

Two Schiff base zinc(II) complexes, [ZnBr₂L¹] · 2CH₃OH (I) (I) and [ZnBr₂L²] (II), where L¹ is 4-chloro-2-[(2-piperazin-1-ylethylimino)methyl]phenol and L² is 4-chloro-2-[(3-diethylaminopropylimino)methyl]phenol were synthesized and structurally characterized. The crystal of I is monoclinic: space group P2₁/c, a = 9.831(3), b = 18.680(6), c = 11.879(4) Å, β = 94.660(6)°, V = 2174.3(11) ų, Z = 4. The crystal of II is monoclinic: space group P2₁/n, a = 7.2310(14), b = 16.037(3), c = 15.856(3), β = 90.01(3)°, V = 1838.7(6) ų, Z = 4. The Zn atom in each complex is four-coordinated by one phenolate O and one imine N atoms of the Schiff base ligand and two bromide atoms, forming a tetrahedral coordination. The urease inhibitory activities of the complexes were evaluated.     

Synthesis,crystal structures,and antibacterial activities of Schiff base nickel(II) and cadmium(II) complexes with tridentate Schiff bases

Reaction of tridentate Schiff bases with nickel and cadmium salts in methanol afforded two new mononuclear complexes, [Ni(L¹)₂] (I) and [Cd(L²)₂] (II), where L¹ and L² are the anions of 2-bromo-4-chloro-6-[(3-dimethylaminopropylimino)methyl]phenol (HL¹) and 2-bromo-4-chloro-6-[(3-morpholin-4-ylpropylimino)methyl]phenol (HL²), respectively. The complexes were characterized by singlecrystal X-ray diffraction (CIF files CCDC nos. 1428653 (I) and 1428654 for (II)), FT-IR, and elemental analysis. Complex I crystallizes in the monoclinic space group P2 ₁/c, with a = 8.8216(8), b = 14.0424(8), c = 11.8687(12) Å, β = 111.238(2)°, V = 1370.4(2) ų, Z = 2. Complex II crystallizes in the monoclinic space group P2 ₁/n, with a = 9.6774(4), b = 15.8970(6), c = 20.3144(7) Å, β = 90.408(2)°, V = 3125.1(2) ų, Z = 4. The metal atoms in the complexes are coordinated by two tridentate Schiff base ligands, forming octahedral coordination. The free Schiff bases and the complexes were assayed for antibacterial activities. Both complexes are more active against the bacteria than the free Schiff bases. Complex II has the MIC value of 0.39 μg mL^–1 against Bacillus subtilis.     

Syntheses and crystal structures of copper(II) and nickel(II) complexes derived from 2-bromo-4-chloro-6-[(2-methylaminoethylimino)methyl]phenol

A new centrosymmetric mononuclear copper(II) complex [Cu(L)₂](ClO₄)₂ (I) and a new centrosymmetric mononuclear nickel(II) complex [Ni(L)₂(MeOH)₂](ClO₄)₂ (II), where L is the zwitterionic ligand 2-bromo-4-chloro-6-[(2-methylammonioethylimino)methyl]phenolate, have been prepared from the Schiff base 2-bromo-4-chloro-6-[(2-methylaminoethylimino)methyl]phenol with copper perchlorate and nickel perchlorate, respectively. The complexes were characterized by elemental analysis, infrared spectra, and single-cyrstal X-ray diffraction (CIF files CCDC nos. 1408054 (I) and 1407973 (II)). Complex I crystallizes in the monoclinic space group P2₁/c with unit cell dimensions a = 7.7736(4), b = 21.608(1), c = 8.5194(4) Å, β = 93.907(2)°, V = 1427.7(1) ų, Z = 2, R ₁ = 0.0546, and wR ₂ = 0.1531. Complex II crystallizes in the monoclinic space group P2₁/c with unit cell dimensions a = 21.324(3), b = 16.821(2), c = 9.425(1) Å, β = 90.114(2)°, V = 3380.5(7) ų, Z = 4, R ₁ = 0.0693, and wR ₂ = 0.1627. The Cu atom in I is in square planar coordination, and the Ni atom in II is in octahedral coordination.     

The crystal and molecular structure of Ni(II) complex with 1-(2-carboxyphenyl)-3-isopropyl-5-(benzimidazole-2-yl)formazane

The binuclear Ni(II) 1-(2-carboxyphenyl)-3-isopropyl-5-(benzimidazole-2-yl)formazanate (Ni₂L₂ · 2H₂O) (I) was synthesized and its crystal and molecule structures were determined by X-ray diffraction. Crystals I are triclinic: space group P \(\bar 1\), a = 7.4811(11), b = 10.8821(15), c = 11.4168(13) Å, α = 105.690(11) Å, β = 90.537(11) Å, γ = 93.166(11) Å, V = 893.2(2) ų, ρ(calcd.) = 1.581 g/cm³, Z = 1.     

Syntheses,characterization, crystal structures and fluorescence property of Zinc(II) complexes with Schiff bases

Two new mononuclear Schiff base zinc(II) complexes, [ZnCl₂(L¹)] ? MeOH (I) and [Zn(L²)₂] (II) (L¹ = 2-bromo-4-chloro-6-[(2-ethylammonioethylimino)methyl]phenolate; L² = 2-bromo-4-chloro-6-(isopropyliminomethyl)phenolate), have been prepared and characterized by elemental analyses, infrared and UV-Vis spectroscopy, and single-cyrstal X-ray diffraction (CIF files CCDC nos. 1408962 (I), 1408961 (II)). Complex I crystallizes in the triclinic space group \(P\overline 1\) with unit cell dimensions a = 9.859(1), b = 13.015(2), c = 19.817(3) Å, α = 73.591(2)°, β = 76.032(2)°, γ = 82.966(2)°, V = 2363.0(5) ų, Z = 4, R ₁ = 0.0925, and wR ₂ = 0.2257. Complex II crystallizes in the monoclinic space group P2₁/c with unit cell dimensions a = 7.6387(7), b = 22.307(2), c = 21.443(2) Å, β = 96.216(3)°, V = 3632.4(6) ų, Z = 8, R ₁ = 0.0651, and wR ₂ = 0.1100. The both Zn atoms in I is four-coordinated in a tetrahedral geometry by the NO donor set of the Schiff base ligand, and two Cl ligands. The Zn atom in II is in a tetrahedral geometry by two N and two O atoms from two Schiff base ligands. Crystals of the complexes are stabilized by hydrogen bonds and weak π…π interactions. Fluorescence property of the complexes have been determined.     

Synthesis and crystal structure of polymeric thiocyanato-bridged copper(II) complex with 4-nitro-2-[(2-piperidin-1ylethylimino)methyl] phenolate

A polymeric thiocyanato-bridged Schiff base copper(II) complex [Cu(L)(NCS)] _n , where L is 4-nitro-2-[(2-piperidin-1-ylethylimino)methyl]phenolate, has been synthesized and structurally characterized by elemental analysis, infrared spectra, and single crystal X-ray diffraction. The complex crystallizes in the monoclinic space group P2₁ with a = 8.527(5), b = 10.296(6), c = 9.697(6) Å, β = 103.77(2)°, V = 826.8(8) ų, Z = 2. In the complex, the Cu atom is in a square pyramidal coordination with one O and two N donor atoms of the Schiff base ligand and with one thiocyanate N atom, defining the basal plane, and with one symmetry related thiocyanate S atom occupying the apical position. The thiocyanate ligand links the Cu atoms through the end-to-end bridging mode.     

Synthesis and crystal structures of cobalt(III) and zinc(II) complexes derived from 4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol with urease inhibitory activity

A new mononuclear cobalt(III) complex, [CoL₂(N₃)]₂ · CH₃OH (I), and a new mononuclear zinc(II) complex, [ZnLCl(CH₃OH)] (II) (HL = 4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol), were prepared and structurally characterized by elemental analyses, infrared spectroscopy, and single- crystal X-ray diffraction. The crystal of I is monoclinic: space group P2₁/c, a = 18.742(2) Å, b = 15.197(2) Å, c = 25.646(2) Å, β = 125.996(3)°, V = 5909.8(11) ų, Z = 4. The crystal of II is monoclinic: space group P2₁/c, a = 7.257(1) Å, b = 24.707(2) Å, c = 9.637(1) Å, β = 101.557(2)°, V = 1692.9(3) ų, Z = 4. The Co atom in I is in an octahedral coordination, and the Zn atom in II is in a trigonal-bipyramidal coordination. The urease inhibitory test shows that complex I has strong urease inhibitory activity, while complex II has no activity.     

Synthesis,characterization, crystal structures,and antimicrobial activity of cobalt(II) and iron(III) complexes derived from N'-(2-hydroxybenzylidene)-3-methylbenzohydrazide

A new cobalt(II,III) complex, [Co^IIIL₂]₂[Co ₂ ^II (HL)₂(OH₂)₂(CH₃OH)₂] ? 2H₂O (I) and a new iron(III) complex, [Fe^III(HL)₂](NO₃) (II), where L^2– and HL^– are the dianionic and monoanionic form of N'-(2-hydroxybenzylidene)-3-methylbenzohydrazide, respectively, have been prepared and characterized by elemental analyses, infrared and UV-Vis spectroscopy and single-cyrstal X-ray diffraction (CIF files CCDC nos. 1417971 (I), 1417979 (II)). Complex I crystallizes in the monoclinic space group P2₁/n with unit cell dimensions a = 16.1665(9), b = 14.5692(8), c = 19.086(1) Å, β = 96.347(1)°, V = 4467.9(4) ų, Z = 2, R ₁ = 0.0521, and wR ₂ = 0.1411. Complex II crystallizes in the orthorhombic space group Pbcn with unit cell dimensions a = 12.475(1), b = 12.202(1), c = 18.859(2) Å, V = 2870.8(4) ų, Z = 4, R ₁ = 0.0796, and wR ₂ = 0.1981. The metal atoms in the complexes are in octahedral coordination. Crystals of the complexes are stabilized by hydrogen bonds. The efficiency of the aroylhydrazone and the two complexes was evaluated against B. subtilis, S. aureus, E. coli, P. fluorescence, C. albicans and A. niger, with the complexes demonstrating enhanced activity relatively to the free ligand.     

Synthesis and crystal structures of cobalt(III) and zinc(II) complexes with Schiff bases

Two new cobalt(III) and zinc(II) complexes, [Co(L¹)₂ (H₂O)] · ClO₄ (I) and [Ni(L²)₂ (H₂O)₂] · 2ClO₄ (II), where L¹ is the deprotonated form of 5-methoxy-2-[(2-morpholin-4-ylethylimino)methyl]phenol, and L² is the zwitterionic form of 2-[(2-isopropylaminoethylimino)methyl]-5-methoxyphenol, were synthesized and structurally characterized by elemental analyses, IR spectra, and single-crystal X-ray diffraction. The crystal of I is monoclinic: space group P2₁/c, a = 11.1512(4), b = 28.2424(11), c = 10.9655(4) Å, β = 95.746(2)°, V = 3436.1(2) ų, Z = 4. The crystal of II is triclinic: space group P2₁/c, a = 8.1441(2), b = 10.4531(3), c = 10.8849(3) Å, α = 84.0240(10)°, β = 76.9800(10)°, γ = 74.2280(10)°, V = 867.92(4) ų, Z = 1. Complex I consists of a mononuclear cobalt(III) complex cation and a perchlorate anion. Complex II consists of a crystallographic centrosymmetric mononuclear nickel(II) complex cation and two perchlorate anions. Each metal atom in the complexes is in an octahedral coordination.     

Syntheses,characterization, and crystal structures of two dinuclear nickel(II) and copper(II) complexes with Schiff bases

The phenolic azide bridged dinuclear nickel(II) complex, [Ni₂(L¹)₂(N₃)(H₂O)(μ_1,1-N₃)] · EtOH (I), and the thiocyanate bridged dinuclear copper(II) complex, [Cu₂(L²)₂(μ_1,1-NCS)₂] (II), where L¹ and L² are the deprotonated forms of 2-mothoxy-6-[(2-piperidin-1-ylethylimino)methyl]phenol and 2,4-dichloro-6-[(2-methylaminoethylimino)methyl]phenol, respectively, were synthesized and characterized by elemental analysis, IR spectra, and single-crystal X-ray diffraction. The crystal of I is orthorhombic: space group Pbca, a = 12.172(1), b = 20.953(1), c = 29.779(2) Å, V = 7594.8(9) ų, Z = 8. The crystal of II is monoclinic: space group P2₁/n, a = 8.7615(11), b = 19.672(2), c = 16.568(2) Å, β = 99.449(2)°, V = 2816.9(6) ų, Z = 4. The Ni atoms in I are in octahedral coordinations, and the Cu atoms in II are in square-pyramidal coordinations.     

Crystal structure of a complex of nickel(II) with 2-amino-4-imino-2-pentene

The structure of a nickel(II) complex with 2-amino-4-iminopentane is determined by X-ray crystallography at 150 K. Crystal data for C₁₀H₁₈N₄Ni are: a = 10.9802(3)Å, b = 13.5780(4)Å, c = 8.0935(2)Å, β = 107.304(1)°, space group P2₁/c, V = 1152.04(5) ų, Z = 4, d _x = 1.459 g/cm³, R = 0.0283. The structure is molecular; the metal atom is coordinated by four nitrogen atoms of two β-diimine ligands. The Ni-N distances in Ni(NacNac)₂ fall within 1.8571–1.8623 Å. The molecules in the crystal are joined by only van der Waals interactions.     

Synthesis and crystal structure of zinc(II) and manganese(II) complexes of 2-(diphenylacetyl)indandione-1,3

Zinc(II) and manganese(II) complexes of 2-(diphenylacetyl)indandione-1,3 (HL) were synthesized. Crystals of [M(DMSO)₂L₂] · CHCl₃, where M= Zn^(II) (I) and Mn^(II) (II), obtained from chloroform plus dimethyl sulfoxide (DMSO) mixture were found to be isostructural based on the similarity of their unit cell parameters and unit cell volumes. The crystals are triclinic, Z = 2, space group P \(\bar 1\); a = 10.422(1) Å, b = 11.929(1) Å, c = 20.429(1) Å, α = 73.616(1)°, β = 85.095(1)°, γ = 77.586(1)° for complex I; a = 10.436(1) Å, b = 12.297(1) Å, c = 19.924(2) Å, α = 78.138(2)°, β = 87.625(2)°, γ = 82.048(2)° for complex II. X-ray structural analysis of complex I was carried out. For complex II, the structure was not refined because all of its atoms are each disordered over three to five positions. The two DMSO molecules in complex I coordinate the central metal atoms in the monodentate mode via their donor oxygen atoms to occupy an axial position and an equatorial position in an octahedral polyhedron. The other four positions are occupied by the four oxygen atoms of the two deprotonated ligands L^? coordinated in the bidentate-cyclic mode. The outer sphere of complex I contains the solvating chloroform molecule.     

Synthesis,crystal structure,and vibrational spectrum of lithium <Emphasis Type="Italic">N</Emphasis>-(4′-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldiminatozinc perchlorate dihydrate

The synthesis, the IR absorption spectrum, and X-ray diffraction analysis of the complex [ZnLi(L¹)₂(H₂O)](ClO₄) · H₂O (I) (HL¹ = N-(4′-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldimine) are described. The crystals of I are monoclinic, a = 19.840(4) Å, b = 13.947(3) Å, c = 19.956(4) Å, β = 117.06(3)°, V = 4917.4(17) ų, Z = 4, space group P2₁/n, R = 0.0609 for 1409 reflections with I > 2σ(I). In the complex cation [ZnLi(L¹)₂(H₂O)]⁺, the Zn atom is bound to a distorted tetrahedral array of two N atoms (av. Zn-N, 2.027(10) Å) and two O atoms (av. Zn-O, 1.8968(8) Å) of two deprotonated L¹ ligands. The Li atom linked to the five ether oxygen atoms (av. Li-O_ether, 2.254(3) Å) sits atop the benzo-15-crown-5 (B15C5) macrocyclic plane of one coordinated L¹ ligand. The Li coordination is completed by water oxygen (Li-O(w1), 1.83(5) Å). The B15C5 cavity of the second coordinated ligand L¹ is vacant.     

Synthesis and crystal and molecular structure of the [Co(HL)Cl<Subscript>2</Subscript>] complex (H<Subscript>2</Subscript>L is an optically active terpene bis-pinane propylenediaminodioxime)

Interaction of Co(II) chloride with optically active bis-pinane propylenediaminodioxime (H₂L) gave a diamagnetic compound of Co(III) with a composition [Co(HL)Cl₂]. The crystal and molecular structure of the compound was determined by X-ray diffraction (XRD) analysis (Enraf-Nonius CAD-4 diffractometer, λMoK_α, 703 F _hkl , R = 0.0347). The crystals are orthorhombic with unit cell parameters a = 8.989(1) Å, b = 12.351(2) Å, c = 22.425(3) Å, V = 2487.7(6) ų, Z = 4, ρ_calc = 1.420 g/cm³, space group P2₁2₁2₁. The crystal structure of the complex is composed of discrete one-center molecules. In the complex, the Co³⁺ ion coordinates four N atoms of the tetradentate cycle-forming ligand (HL^? anion) and two Cl atoms. The coordination polyhedron of Co is a distorted octahedron Cl₂N₄.     

Synthesis and crystal structure of a new Schiff base ligand and its cobalt(II) complex

The crystal structures of cobalt(II) Schiff base complex (Co^IIL₂ · H₂O) and Schiff base ligand 3,5-dichlorosalicylidene-2-chlorophenylmethylamine (HL) have been determined by single-crystal X-ray analysis. The geometry around cobalt in Co^IIL₂ · H₂O is distorted tetrahedral. Co^IIL₂ · H₂O crystallizes in the monoclinic system, in space group C2/c, with crystallographic parameters: a = 12.9143(16) Å, b = 8.8326(16) Å, c = 25.115(3) Å, β = 92.791(10)°, V = 2861.4(7) ų, Z = 4, F(000) = 1420, and the final R indices (I > 2σ(I)) are R ₁ = 0.0440, wR ₂ = 0.1272. HL crystallizes in the monoclinic system, in space group P2₁/c, with crystallographic parameters: a = 11.9764(15), b = 8.2331(10), c = 14.2211(17) Å, β = 98.723(6)°, V = 1386.0(3) ų, Z = 4, F(000) = 640, and the final R indices (I > 2σ(I)) are R ₁ = 0.0397, wR ₂ = 0.1018.     

Synthesis and crystal structures of two zinc(II) complexes derived from 4-bromo-2-(cyclopentyliminomethyl)phenol with different solvents

Two new mononuclear zinc(II) complexes, [ZnL₂] (I) and [ZnL₂] · 2MeOH (II) (HL = 4-bromo-2-(cyclopentyliminomethyl)phenol), were synthesized by the reaction of the Schiff base HL with zinc acetate in ethanol and methanol solutions, respectively. Both complexes were characterized by elemental analyses and single-crystal X-ray diffraction. The crystal of I is orthorhombic: space group Pbca, a = 14.711(3), b = 13.223(3), c = 24.870(5) Å, V = 4837.8(18) ų, Z = 8. The crystal of II is monoclinic: space group C2/c, a = 20.581(5), b = 10.660(3), c = 15.428(4) Å, β = 119.919(3)°, V = 2933.7(13) ų, Z = 4. The Zn atom in each complex is four-coordinated by two imine N and two phenolic O atoms, forming a tetrahedral geometry. Complex II possesses crystallographic two-fold rotation axis symmetry.     

Synthesis and crystal structures of the zinc(II) complexes with a tridentate Schiff base (1-pyridin-2-ylethylidene)pyridin-2-ylmethylamine

Two new isostructural zinc(II) complexes, [ZnCl₂(L)] (I) and [ZnBr₂(L)] (II), derived from the Schiff base ligand (1-pyridin-2-ylethylidene)pyridin-2-ylmethylamine (L), have been prepared and characterized by physicochemical methods and single-crystal X-ray crystallography. The crystal of I is monoclinic: space group P2₁/c, a = 11.699(3) Å, b = 8.460(2) Å, c = 14.766(3) Å, β = 99.686(3)°, V = 1440.6(6) ų, Z = 4. The crystal of II is monoclinic: space group P2₁/n, a = 8.166(2) Å, b = 15.153(3) Å, c = 11.966(2) Å, β = 96.964(2)°, V = 1469.7(5) ų, Z = 4. The geometry of the pentacoordinated zinc atoms in both complexes is best described as a square pyramid.     

Crystal structure and fluorescence of a 2D cadmium(II) coordination polymer based on flexible bis(2-methylbenzimidazole) and benzenedicarboxylate co-ligands

A new coordination polymer, {[Cd(bbmb)(bdc)]} _n (bbmb = 1,1′-(1,4-butanediyl)bis-(2-methylbenzimidazole), H₂bdc = 1,3-benzenedicarboxylic acid) was synthesized under hydrothermal conditions. The complex was structurally characterized by single crystal X-ray diffraction analyses, infrared spectroscopy (IR), elemental analyses. The compound crystallizes in the monoclinic system, space group P2₁/c with a = 10.860(6) Å, b = 13.115(7) Å, c = 21.009(9) Å, β = 120.94(2)°, V = 2567(2) ų, Z = 4, C₂₈H₂₆CdN₄O₄, M _r = 594.93, D _c = 1.540 g/cm³, μ = 0.893 mm^–1. Each cadmium center is six coordinated with four O atoms from two bdc^2– anions, and two N atoms of two bbmb ligands. The complex features a 4-connected 2D (4, 4) sheet with a point symbol {4².6^2}. Fluorescence properties of the title complex were investigated.