Home Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn
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Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn

  • Ji-Xing Zhao ORCID logo EMAIL logo
Published/Copyright: October 9, 2019

Abstract

C33H32F2N4O5Zn, triclinic, P1̄ (no. 2), a = 9.5132(5) Å, b = 13.0781(6) Å, c = 14.0448(6) Å, α = 63.0950(10)°, β = 73.5640(10)°, γ = 78.870(2)°, V = 1490.24(12) Å3, Z = 2, Rgt(F) = 0.0459, wRref(F2) = 0.1004, T = 173(2) K.

CCDC no.: 1952874

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.21 × 0.19 × 0.16 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.89 mm−1
Diffractometer, scan mode:APEX2, φ and ω
θmax, completeness:26.8°, 98%
N(hkl)measured, N(hkl)unique, Rint:24583, 6216, 0.074
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4570
N(param)refined:412
Programs:Bruker [1], SHELX [2], Olex2 [3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
C11.0539(3)0.7570(2)0.5526(2)0.0319(7)
C21.1295(3)0.8561(3)0.5142(2)0.0355(7)
H21.1891470.8602390.5562350.043*
C31.1164(3)0.9455(2)0.4169(3)0.0368(7)
C41.0323(3)0.9475(3)0.3507(3)0.0431(8)
H41.0246931.0126310.2839100.052*
C50.9603(3)0.8515(3)0.3856(2)0.0389(7)
H50.9027310.8501010.3409150.047*
C60.9681(3)0.7546(2)0.4853(2)0.0314(6)
C70.8859(3)0.6613(2)0.5099(2)0.0325(7)
H70.8385340.6706460.4550340.039*
C80.7811(3)0.4811(2)0.6082(2)0.0280(6)
C90.7418(3)0.4800(3)0.5206(2)0.0342(7)
H90.7689630.5393130.4491240.041*
C100.6635(3)0.3929(3)0.5376(2)0.0354(7)
H100.6365320.3937780.4770190.042*
C110.6221(3)0.3030(2)0.6413(2)0.0302(6)
C120.6601(3)0.3063(2)0.7286(2)0.0337(7)
H120.6317340.2476740.8003170.040*
C130.7385(3)0.3935(2)0.7123(2)0.0333(7)
H130.7638240.3937590.7728930.040*
C140.5483(3)0.2055(2)0.6556(2)0.0333(7)
C150.5461(4)0.0934(3)0.7549(3)0.0441(8)
H15A0.4469530.0847660.8019830.066*
H15B0.6156590.0920300.7954650.066*
H15C0.5743730.0301500.7324250.066*
C160.4182(4)0.1392(3)0.4880(3)0.0486(8)
H16A0.5164540.1319260.4436910.073*
H16B0.3703890.2152150.4504800.073*
H16C0.3593720.0795950.4984480.073*
C171.1093(3)0.3376(2)0.8604(2)0.0347(7)
C181.2247(3)0.2503(3)0.8777(3)0.0438(8)
H181.2865560.2372750.8174460.053*
C191.2479(3)0.1847(3)0.9803(3)0.0411(8)
C201.1650(3)0.1981(2)1.0722(3)0.0365(7)
H201.1856200.1514271.1424380.044*
C211.0516(3)0.2819(2)1.0576(2)0.0328(7)
H210.9916800.2921651.1198760.039*
C221.0196(3)0.3536(2)0.9540(2)0.0280(6)
C230.8974(3)0.4369(2)0.9536(2)0.0297(6)
H230.8448670.4341361.0230460.036*
C240.7233(3)0.5911(2)0.8841(2)0.0273(6)
C250.6340(4)0.5788(3)0.9837(3)0.0528(10)
H250.6574250.5179981.0485620.063*
C260.5116(4)0.6523(3)0.9917(3)0.0489(9)
H260.4534390.6419261.0622150.059*
C270.4708(3)0.7406(2)0.9005(2)0.0306(6)
C280.5646(4)0.7560(3)0.8007(3)0.0507(9)
H280.5432140.8185330.7360380.061*
C290.6890(4)0.6827(3)0.7925(3)0.0485(9)
H290.7515000.6959620.7226350.058*
C300.3345(3)0.8165(2)0.9083(2)0.0310(6)
C310.2685(3)0.8826(3)0.8100(3)0.0417(8)
H31A0.1660480.9081190.8331600.063*
H31B0.2721390.8331880.7735960.063*
H31C0.3241900.9497350.7589690.063*
C320.0946(4)0.8895(3)1.1075(3)0.0494(9)
H32A0.0029940.9388741.1083620.074*
H32B0.1672100.9177771.1255130.074*
H32C0.0755420.8105661.1616980.074*
F11.3612(2)0.10248(17)0.99304(16)0.0609(6)
F21.19074(19)1.04000(15)0.38320(15)0.0494(5)
N10.8499(2)0.51591(19)0.86919(18)0.0271(5)
N20.2791(3)0.8177(2)1.0028(2)0.0374(6)
N30.8678(2)0.56501(19)0.59846(18)0.0286(5)
N40.4940(3)0.2238(2)0.5740(2)0.0394(6)
O11.0903(2)0.39835(18)0.76039(16)0.0412(5)
O20.1500(2)0.89126(18)1.00110(17)0.0445(6)
O31.0663(2)0.67293(17)0.64792(16)0.0365(5)
O40.4304(2)0.12574(18)0.59212(18)0.0464(6)
Zn10.96309(4)0.53484(3)0.71929(3)0.03157(11)
C331.3990(4)0.5684(3)0.7315(3)0.0581(10)
H33A1.4408270.6146860.6540700.087*
H33B1.3706200.4960120.7400880.087*
H33C1.4724140.5518160.7745060.087*
O51.2736(3)0.6299(2)0.7690(2)0.0574(7)
H5A1.2136010.6488280.7289060.086*

Source of material

Synthesis of the ligand: 4-Amino acetophenone methoxy oxime was prepared by a similar method for related compounds reported earlier by us [4], [5], [6]. 4-Fluoro-2-hydroxy-benzaldehyde (420 mg, 3 mmol) in EtOH (5 mL) was added to 4-amino acetophenone methoxy oxime (492.6, 3 mmol) in EtOH (5 mL). The product was filtered and dried under vacuum. A yellow solid was obtained.

Synthesis of the zinc(II) complex: The zinc acetate dihydrate (219.5 mg, 1 mmol) in MeOH (4 mL) and the synthesized ligand (572.6 mg, 2 mmol) in CH2Cl2 (4 mL) were combined forming a light yellow mixture at room temperature. After being stirred for 2 h at room temperature, the filtrate was allowed to stand for 13 days. Several clear light yellow crystals were obtained. Anal. Calcd. for C33H32F2N4O5Zn: C, 59.33%; H, 4.83%; N, 8.39%. Found: C, 59.74%; H, 5.07%; N, 8.11%.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Comment

A wide variety of Schiff base ligands have been proverbially used to prepare transition metal complexes for several decades. Schiff base ligands can be coordinated with transition-metal ions to form mononuclear or multinuclear stable complexes [7], [8], [9], [10]. So far, we have designed and synthesized a variety of Schiff base N2O2 type complexes [6], [8], [11], [12], [13], [14] and others [15], [16].

The title complex presents a symmetric mononuclear structure. In the title complex, Zn1 is four-coordinated by two O atoms and two N atoms from two Schiff base ligands. In the title crystal, there is a strong intermolecular O5–H5A⋯O3 hydrogen bond between the OH group of methanol molecule and the phenolato oxygen atom O3 (cf. the figure) (d(O5–H5A) = 0.84, d(O3⋯H5A) = 1.940 and d(O5⋯O3) = 2.775). All geometric parameters are in the typical ranges.

References

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Received: 2019-07-12
Accepted: 2019-09-11
Published Online: 2019-10-09
Published in Print: 2019-12-18

©2019 Ji-Xing Zhao, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  57. Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
  58. Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
  59. Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
  60. Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
  61. Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
  62. Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
  63. The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
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