Home Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′:O′}trizinc(II), C44H49Cl2N6O12Zn3
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Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′:O′}trizinc(II), C44H49Cl2N6O12Zn3

  • Li Li , Jing Hao , Peng-Fei Lan and Wen-Kui Dong EMAIL logo
Published/Copyright: October 12, 2017

Abstract

C44H49Cl2N6O12Zn3, monoclinic, P1̅ (no. 2), a = 9.7387(8) Å, b = 13.7034(12) Å, c = 20.2498(16) Å, α = 72.539(8)°, β = 82.872(7)°, γ = 72.157(8)°, Z = 2, V = 2452.3(4) Å3, Rgt(F) = 0.0604, wRref(F2) = 0.1392, T = 293(2) K.

CCDC no.:: 1571007

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Clear light yellow block
Size:0.20 × 0.15 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.63 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax26.0°
N(hkl)measured, N(hkl)unique, Rint:16652, 9456, 0.119
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4735
N(param)refined:629
Programs:CrysAlisPRO [17], SHELX [18]
Table 2

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

xyzUiso*/Ueq
Zn10.66226(10)1.10928(8)0.36632(5)0.0579(3)
Zn20.84169(9)0.98703(7)0.26781(4)0.0463(3)
Zn30.96220(9)0.87614(7)0.15526(4)0.0466(3)
Cl10.9101(3)1.5470(2)0.12327(15)0.0979(9)
Cl20.9566(4)0.3986(2)0.44200(14)0.1146(11)
O10.7683(6)1.1516(4)0.2780(3)0.0583(15)
O20.6231(7)1.2762(5)0.4507(3)0.088(2)
O30.3732(7)1.2378(6)0.4061(4)0.103(2)
O40.6410(5)1.0013(4)0.3185(2)0.0487(13)
O50.9202(5)0.8247(4)0.2558(2)0.0512(14)
O61.1847(6)0.6856(4)0.1071(3)0.0672(17)
O70.9190(6)0.7997(4)0.0363(3)0.0661(17)
O80.7888(5)1.0039(4)0.1671(2)0.0484(13)
O90.7917(5)1.0044(4)0.4401(3)0.0581(15)
O100.9361(5)0.9298(4)0.3641(2)0.0513(14)
O111.0329(5)1.0161(4)0.2275(3)0.0502(14)
O121.1137(5)0.9495(4)0.1373(2)0.0544(15)
N10.6740(8)1.2490(5)0.3881(4)0.065(2)
N20.4497(8)1.1399(6)0.3889(4)0.078(2)
N30.4570(9)0.7425(7)0.2752(4)0.083(3)
N41.0913(6)0.7171(5)0.1612(3)0.0515(17)
N50.8694(7)0.8870(5)0.0682(3)0.0547(19)
N60.3801(9)1.3050(7)0.1172(5)0.097(3)
C10.8052(9)1.2390(7)0.2460(4)0.059(2)
C20.8590(8)1.2554(6)0.1772(4)0.054(2)
H20.8725061.2016300.1557790.064*
C30.8923(9)1.3472(7)0.1403(5)0.069(3)
H30.9287311.3550020.0949140.082*
C40.8714(9)1.4274(7)0.1709(5)0.068(3)
C50.8223(9)1.4152(7)0.2375(5)0.072(3)
H50.8134451.4694080.2577790.087*
C60.7844(9)1.3235(7)0.2768(5)0.064(2)
C70.7230(9)1.3216(7)0.3469(5)0.065(3)
H70.7197851.3793710.3627170.078*
C80.5501(13)1.2049(9)0.4925(5)0.092(4)
H8A0.5545761.2041230.5402840.110*
H8B0.6019371.1339670.4886710.110*
C90.3978(12)1.2260(9)0.4777(5)0.106(4)
H9A0.3625051.1678710.5072320.127*
H9B0.3418301.2907150.4896370.127*
C100.3600(10)1.0952(9)0.3766(5)0.079(3)
H100.2628361.1243920.3865520.095*
C110.3942(9)1.0081(8)0.3499(4)0.067(3)
C120.5289(8)0.9663(6)0.3200(4)0.052(2)
C130.5465(7)0.8789(6)0.2945(4)0.052(2)
H130.6344180.8522440.2731770.063*
C140.4367(9)0.8295(7)0.2998(4)0.062(2)
C150.2993(9)0.8747(8)0.3289(4)0.077(3)
H150.2230900.8456220.3327320.093*
C160.2844(9)0.9617(8)0.3508(5)0.080(3)
H160.1936420.9931940.3677460.095*
C170.3503(12)0.6813(10)0.2897(7)0.122(5)
H17A0.3687230.6380660.2576570.146*
H17B0.2545330.7308010.2815560.146*
C180.3536(16)0.6089(12)0.3636(8)0.207(8)
H18A0.2956040.5619300.3674850.311*
H18B0.3160860.6516910.3951340.311*
H18C0.4512810.5675900.3745510.311*
C190.5850(10)0.7027(8)0.2374(6)0.087(3)
H19A0.5973670.6281740.2415640.105*
H19B0.6675920.7071180.2574620.105*
C200.5811(13)0.7633(9)0.1624(6)0.132(5)
H20A0.6695490.7343890.1392340.198*
H20B0.5697150.8370280.1579520.198*
H20C0.5013660.7572220.1419070.198*
C210.9332(8)0.7275(7)0.2972(4)0.047(2)
C220.8666(8)0.7126(6)0.3630(4)0.051(2)
H220.8162230.7723840.3777530.061*
C230.8725(9)0.6130(8)0.4072(4)0.070(3)
H230.8244290.6059100.4502870.084*
C240.9513(10)0.5235(7)0.3863(4)0.068(3)
C251.0189(9)0.5344(7)0.3236(5)0.066(3)
H251.0711870.4735500.3104780.079*
C261.0128(8)0.6347(6)0.2774(4)0.051(2)
C271.0917(8)0.6341(6)0.2126(4)0.051(2)
H271.1478510.5683620.2073060.061*
C281.1778(9)0.7719(7)0.0491(4)0.061(2)
H28A1.2681160.7586570.0224540.073*
H28B1.1677670.8347580.0640640.073*
C291.0583(10)0.7946(7)0.0036(4)0.076(3)
H29A1.0529000.862154−0.0310320.091*
H29B1.0819820.739922−0.0206170.091*
C300.7522(10)0.9568(7)0.0402(4)0.060(2)
H300.7233310.9487330.0005620.072*
C310.6664(8)1.0421(7)0.0640(4)0.051(2)
C320.6827(8)1.0661(6)0.1253(4)0.0430(18)
C330.5839(7)1.1530(6)0.1418(4)0.055(2)
H330.5921821.1655450.1835930.066*
C340.4744(8)1.2214(7)0.0998(4)0.060(2)
C350.4586(8)1.1997(7)0.0368(4)0.057(2)
H350.3867371.2450330.0064050.069*
C360.5511(9)1.1116(7)0.0225(4)0.054(2)
H360.5373891.095969−0.0174460.064*
C370.2673(13)1.3796(11)0.0714(7)0.123(5)
H37A0.1907121.4164140.0983350.148*
H37B0.2267121.3405190.0500810.148*
C380.3223(17)1.4591(11)0.0166(8)0.180(7)
H38A0.3787111.4882230.0370120.270*
H38B0.2425211.515370−0.0063090.270*
H38C0.3814191.425188−0.0164240.270*
C410.9036(8)0.9387(6)0.4239(4)0.0435(19)
C421.0001(8)0.8685(6)0.4809(4)0.065(2)
H42A0.9492750.8245860.5144410.098*
H42B1.0303670.9114740.5026970.098*
H42C1.0831840.8240150.4627140.098*
C431.1174(8)1.0033(6)0.1782(4)0.0461(19)
C441.2339(8)1.0602(6)0.1622(4)0.054(2)
H44A1.2284461.0971560.1963020.081*
H44B1.2201491.1105230.1171240.081*
H44C1.3269661.0089280.1629270.081*
C390.365(3)1.312(2)0.1880(8)0.090(8)
H39A0.2625501.3391080.1985720.108*
H39B0.3976721.2404770.2182960.108*
C400.438(3)1.3775(19)0.2062(15)0.133(10)
H40A0.5399641.3527890.1961370.200*
H40B0.4222701.3723450.2547110.200*
H40C0.4015301.4504620.1797850.200*
C39′0.427(3)1.355(2)0.1678(12)0.104(9)
H39C0.5295801.3284930.1757340.125*
H39D0.3962341.4321820.1535930.125*
C40′0.337(3)1.307(2)0.2287(11)0.110(8)
H40D0.2360391.3428740.2209180.166*
H40E0.3622981.3154930.2704830.166*
H40F0.3544181.2324300.2331440.166*

Source of material

A solution of zinc(II) acetate hydrate (3.32 mg, 0.015 mmol) in ethanol (3 mL) was added dropwise to a solution of H2L 4-(diethylamino)-2-hydroxybenzaldehyde O-(2-(((5-chloro-2-hydroxybenzylidene)amino)oxy)ethyl) oxime (3.98 mg, 0.010 mmol) in acetonitrile (2 mL) at room temperature. The color of the mixing solution turned yellow immediately, the mixture was filtered and the filtrate was allowed to stand at room temperature for about two weeks. The solvent was partially evaporated and clear light colourless single crystals were obtained. Yield: 58%. Elemental analysis-anal. calcd. for C44H50Cl2N6O12Zn3: C, 47.10%; H, 4.49%; N, 7.49%. Found: C, 47.05%; H, 4.46%; N, 7.36%.

Experimental details

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

Discussion

Salen-type compounds and their transition metal complexes have been investigated for many decades with a focus on modified ligand systems in the last years [1], [2], [3], [4]. New research fields are the use of such complexes in a very wide and diversified subjects such as, optical and magnetic materials [5], [6], [7], [8], [9], [10] and supramolecular architectures [11], [12], [13], [14], [15], [16].

The structure is built up by one C44H50Cl2N6O12Zn3 complex. The assembly of three Zn(II) ions, two completely deprotonated (L)2− units, two acetate ions result in an unsymmetrical trinuclear Zn(II) complex. The coordination sphere of penta-coordinated terminal Zn2 or Zn3 atoms is completed by N2O2 donor atoms (O3, O8, N4 and N14 or O9, O15, N19 and N25) and one oxygen atom (O13 or O17) of the acetate ion, adopting a trigonal bipyramidal geometry with axial donor atoms (O8 and N14 or O9 and N25). The coordination sphere of the hexa-coordinated central Zn1 atom is completed by four phenolato oxygen atoms (O3, O8, O9 and O15) and two oxygen atoms (O10 and O11) of the two acetate ions, to form a octahedral coordination geometry. The two acetate ligands bridge the three Zn metal centers in typicall κ2O:O′-mode (cf. the figure).

References

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Received: 2017-3-21
Accepted: 2017-8-27
Published Online: 2017-10-12
Published in Print: 2017-11-27

©2017 Li Li et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  26. Crystal structure of catena-poly[(μ2-benzene-1,4-dicarboxylato-κ2O:O′)-(1-ethyl-6-fluoro-7-(4-methylpiperazin-1-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato-κ2O,O′)zinc(II)] 1.25 hydrate, C25H26.5N3O8.25FZn
  27. Crystal structure of 1-methyl-1,4-diazabicyclo[2.2.2]octan-1-ium poly[aqua-bis(μ2-perchlorato-κ3O,O′:O′′)sodium], C7H17Cl2N2NaO9
  28. Crystal structure of trimethyammonium 2,6-dicarboxyisonicotinate monohydrate, C11H16N2O7
  29. Crystal structure of dodecaguanidinium bis(tetrapropylammonium) heptacarbonate, C43H128N38O21
  30. Crystal structure of poly[tetraaqua-bis(μ6-benzene-1,2,4,5-tetracarboxylato)nickel(II)diyttrium(III)]dihydrate, C20H16NiO22Y2
  31. Halogen bonds and π–π interactions in the crystal structure of 1,3,5-trifluoro-2,4,6-triiodobenzene–N,N-dimethylformamide (1/1), C9H7F3I3NO
  32. Crystal structure of guanidinium tetraethylammonium carbonate dihydrate, C10H30N4O5
  33. The crystal structure of oxonium chlorido-ethylenediaminetetraactetotin(IV) hydrate, C10H17ClN2O10Sn
  34. Crystal structure of 8-((E)-((4-((E)-1-((benzyloxy)imino)ethyl)phenyl)imino)methyl)-7-hydroxy-4-methyl-2H-chromen-2-one, C26H22N2O4
  35. Crystal structure of bis{5-(diethylamino)-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2O,N}copper(II), C40H38CuN4O6
  36. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri(p-tolyl)phosphine-κP)rhenium(I), C29H28O5PRe
  37. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(benzyldiphenylphosphine-κP)rhenium(I), C27H24O5PRe
  38. Crystal structure of triethylammonium bis{3-(((3-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}manganese(III), C46H38MnN3O8
  39. Crystal structure of bis(N,N,N-ethyldimethylethanaminium) bis(heptaselenido-κ2Se1,Se7)palladate(II), C12H32N2PdSe14
  40. Crystal structure of bis(4-(1H-pyrazol-5-yl)pyridine-κ2N:N′)-bis(2-(2-((2,6-difluorophenyl)amino)phenyl)acetate-κO)cadmium(II), C44H34N8CdCl4O4
  41. Crystal structure of 4,4′-(1,4-phenylene)bis(pyridin-1-ium) catena-poly[diaqua-bis(μ2-3′,5′-dicarboxy-[1,1′-biphenyl]-2,5-dicarboxylato-κ2O:O′] dihydrate, C48H42O22N2Ca
  42. The crystal structure of (S)-2-benzylsuccinic acid, C11H12O4
  43. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)yttrium(III)], C26H17N2O9Y
  44. Crystal structure of ethyl 1-(3,4-dimethylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate, C14H17N3O2
  45. Crystal structure of tetrakis(methanol-κO)-bis{μ2-3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olate-κ4O,N;O′:O′}dizinc(II), C38H38Zn2N2O14
  46. Crystal structure of bromido(4,4′-dimethoxy-2,2′-bipyridine-κ2N,N′)(isopropyl(diphenyl)phosphane-κP)copper(I), C27H29BrCuN2O2P
  47. Crystal structure of bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dioctylfluorene, C41H64B2O4
  48. Crystal structure of 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde - a julolidine derivative, C16H15NO3
  49. Crystal structure of 1,3-dimethyl-5,5-dibenzylbarbituric acid, C20H20N2O3
  50. Crystal structure of bis(N,N,N-trimethylethanaminium) poly[bis(μ2-heptaselenido-κ2Se1,Se7)palladate(II)], C10H28N2PdSe14
  51. Crystal structure of 1-{4-[(5-Chloro-2-hydroxy-benzylidene)amino]phenyl} ethanone O-ethyl-oxime, C17H17ClN2O2
  52. The crystal structure of methyl N-(4-bromophenyl)carbamate, C8H8BrNO2
  53. Synthesis and crystal structure of 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone oxime, C15H14N2O2
  54. Crystal structure of 1,1′-butanebis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C12H20F12N4P2
  55. (E)-N-benzylidene-3-(benzylthio)-5-p-tolyl-4H-1,2,4-triazol-4-amine, C23H20N4S
  56. Crystal structure of ethyl 5-methyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate, C11H12N4O2
  57. Crystal structure of 5,5-difluoro-10-(4-fluorophenyl)-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine - a Z′ = 3 structure, C19H18B2F3N2
  58. The crystal structure of the Matrine derivative: 12-(1H-indol-1-yl)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one hydrate, C23H29N3O
  59. The crystal structure of tris(μ2-1,3-bis(4,4,4-trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-κ2O,O′)dilutetium(III), C50H38F18Lu2O16
  60. The crystal structure of (Z)-2-(3-(2-(4-chlorobenzoyl)hydrazono)-2-oxoindolin-1-yl) acetic acid, C17H12ClN3O4
  61. Synthesis and crystal structure of trans-tetraqua-bis(2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetato-κO)cobalt(II) hexahydrate, C36H48CoN2O28S2
  62. The crystal structure of N,N-dimethyl-2,6-di-p-tolylpyrimidin-4-amine, C20H21N3
  63. The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C14H13N3O4S
  64. Crystal structure of catena-poly[(μ2-1,3-bis(benzimidazol-1-yl)propane κ2N:N′)-(μ2-5-methoxyisophthalato-κ2O:O′)zinc(II)] hydrate, C26H24ZnN4O6
  65. The crystal structure of (E)-N′-(quinolin-2-ylmethylene)furan-2-carbohydrazide monohydrate, C15H13N3O3
  66. Crystal structure of 2,8-diphenyl-3,7,9-trioxa-1-azaspiro[4.5]dec-1-ene, C18H17N1O3
  67. Crystal structure of diethyl 2-(4-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19ClO6
  68. Crystal structure of 1-(carboxymethyl)-1H-benzo[d][1,2,3]triazole 3-oxide, C8H7N3O3
  69. Crystal structure of (acetylacetonato-κ2O,O′)-(2-amino-6-chlorobenzoato-κO)-oxido(1,10-phenanthroline-κ2N,N′)vanadium(IV) – trichloromethane (1/1)
  70. Crystal structure of (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one, C17H12Cl2O
  71. The crystal structure of trans-dibromido-bis(pyridine-κN)platinum(II), C10H10Br2N2Pt
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