Home Crystal structure of triethylammonium bis{3-(((3-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}manganese(III), C46H38MnN3O8
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Crystal structure of triethylammonium bis{3-(((3-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}manganese(III), C46H38MnN3O8

  • Jing Li , Hao-Ran Jia and Yin-Xia Sun EMAIL logo
Published/Copyright: October 16, 2017

Abstract

C46H38MnN3O8, triclinic P1̅ (no. 2), a = 8.9705(6) Å, b = 12.0309(8) Å, c = 18.4209(13) Å, α = 96.303(2)°, β = 103.884(2)°, γ = 101.636(2)°, Z = 2, V = 1864.0(2) Å3, Rgt(F) = 0.0496, wRref(F2) = 0.1274, T = 296 K.

CCDC no.: 1540633

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:Prismatical, dark reddish brown
Size:0.17 × 0.15 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.42 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:12833, 6523, 0.033
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5038
N(param)refined:526
Programs:Bruker programs [1], SHELX [2]
Table 2

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

AtomxyzUiso*/Ueq
C10.4669(3)0.4124(2)0.23705(17)0.0231(7)
C20.3454(4)0.4191(3)0.27364(18)0.0286(7)
H20.36080.48110.31180.034*
C30.2078(4)0.3375(3)0.25426(18)0.0295(7)
H30.13010.34550.27860.035*
C40.1797(4)0.2399(3)0.19753(18)0.0283(7)
C50.0357(4)0.1556(3)0.1779(2)0.0353(8)
H5−0.04240.16460.20190.042*
C60.0099(4)0.0606(3)0.1241(2)0.0404(9)
H6−0.08560.00580.11140.048*
C70.1276(4)0.0463(3)0.0884(2)0.0374(8)
H70.1110−0.01920.05280.045*
C80.2674(4)0.1283(3)0.10543(18)0.0300(7)
H80.34360.11770.08060.036*
C90.2982(3)0.2284(2)0.15997(17)0.0235(7)
C100.4441(3)0.3178(2)0.17967(17)0.0223(7)
C110.5565(3)0.3090(2)0.13771(16)0.0197(6)
H110.52850.24790.09770.024*
C120.8060(3)0.3636(2)0.10817(16)0.0197(6)
C130.9455(3)0.4473(2)0.13228(16)0.0194(6)
C141.0656(3)0.4444(2)0.09275(16)0.0208(6)
C151.2109(3)0.5256(3)0.11230(17)0.0244(7)
H151.23540.58370.15390.029*
C161.3170(4)0.5195(3)0.07032(18)0.0277(7)
H161.41310.57370.08340.033*
C171.2813(4)0.4323(3)0.00795(17)0.0279(7)
H171.35320.4295−0.02070.033*
C181.1410(4)0.3506(3)−0.01153(17)0.0263(7)
H181.11770.2924−0.05300.032*
C191.0348(3)0.3562(2)0.03159(17)0.0221(7)
C200.7786(4)0.2700(3)0.04741(17)0.0251(7)
C210.6400(3)0.8090(3)0.12853(18)0.0269(7)
H210.60170.77140.07860.032*
C220.6246(4)0.9168(3)0.14491(19)0.0289(7)
H220.57570.95180.10640.035*
C230.6827(3)0.9790(3)0.22116(19)0.0265(7)
C240.6620(4)1.0913(3)0.2381(2)0.0342(8)
H240.61171.12510.19920.041*
C250.7142(4)1.1515(3)0.3104(2)0.0383(9)
H250.69921.22530.32070.046*
C260.7901(4)1.1009(3)0.3685(2)0.0377(9)
H260.82601.14130.41780.045*
C270.8129(4)0.9912(3)0.35373(19)0.0301(8)
H270.86400.95910.39340.036*
C280.7600(3)0.9269(2)0.27943(18)0.0236(7)
C290.7761(3)0.8087(2)0.26148(17)0.0221(7)
C300.7138(3)0.7493(2)0.18571(18)0.0235(7)
C310.8644(3)0.7608(2)0.31898(17)0.0211(6)
H310.90500.80760.36620.025*
C321.0061(3)0.6304(2)0.37516(16)0.0217(7)
C331.1233(4)0.7128(3)0.43132(17)0.0265(7)
C341.2151(4)0.5608(3)0.48944(18)0.0280(7)
C351.3204(4)0.5335(3)0.55032(18)0.0334(8)
H351.39250.59090.58730.040*
C361.3142(4)0.4199(3)0.5537(2)0.0381(9)
H361.38170.39970.59420.046*
C371.2090(4)0.3342(3)0.49798(19)0.0347(8)
H371.20760.25740.50120.042*
C381.1065(4)0.3616(3)0.43794(19)0.0307(8)
H381.03620.30370.40070.037*
C391.1086(4)0.4772(3)0.43326(18)0.0272(7)
C400.9981(4)0.5108(3)0.37218(17)0.0240(7)
C410.2677(5)0.8293(3)0.1835(2)0.0477(10)
H41A0.28860.90890.17790.072*
H41B0.20510.78300.13600.072*
H41C0.36580.80670.19880.072*
C420.1800(4)0.8125(3)0.2423(2)0.0435(9)
H42A0.17070.73410.25200.052*
H42B0.07400.82260.22260.052*
C430.4286(4)0.8970(3)0.3482(2)0.0418(9)
H43A0.46860.94680.39710.050*
H43B0.48720.92940.31450.050*
C440.4577(5)0.7782(3)0.3573(3)0.0578(12)
H44A0.39740.74450.38930.087*
H44B0.56810.78510.37980.087*
H44C0.42590.73000.30850.087*
C450.2343(5)1.0136(3)0.3093(2)0.0533(11)
H45A0.12311.00830.28690.064*
H45B0.29251.04500.27520.064*
C460.2879(7)1.0942(4)0.3841(3)0.0824(17)
H46A0.25651.05440.42240.124*
H46B0.24061.15880.37950.124*
H46C0.40091.12080.39810.124*
Mn10.78383(5)0.52108(4)0.22835(3)0.02027(14)
N10.8969(3)0.65847(19)0.31452(13)0.0198(5)
N20.6963(3)0.37907(19)0.15018(13)0.0193(5)
N30.2583(3)0.8950(2)0.31728(17)0.0377(7)
O10.6636(2)0.18934(18)0.02407(12)0.0326(6)
O20.8964(2)0.27109(17)0.01051(11)0.0256(5)
O30.5941(2)0.49792(17)0.25790(12)0.0271(5)
O40.9674(2)0.52927(16)0.18929(11)0.0223(5)
O51.1517(2)0.81926(17)0.43653(12)0.0303(5)
H3A0.20090.86770.35670.036*
O61.2245(3)0.67639(18)0.48821(12)0.0308(5)
O70.7210(2)0.64531(16)0.16512(11)0.0241(5)
O80.8983(2)0.43668(17)0.31846(11)0.0264(5)

Source of material

Synthesis of the ligand: The ligand was synthesized according to an analogous method reported previously in the literature [3], [4] . To an ethanol solution (5 mL) of 2-hydroxy-1-naphthaldehyde (172.2 mg, 1 mmol) was added an ethanol solution (5 mL) of 3-amino-4-hydroxy-2H-chromen-2-one (177.2 mg, 1 mmol). The solution was stirred under reflux conditions at 328 K for 8 h. After cooling to room temperature, the precipitate was filtered and washed with ethanol and hexane. The product was dried under vacuum and obtained orange-yellow solid (yield 78.7%, m.p. 554-555 K). Elemental analysis-Anal. calcd. for C20H13NO4 (%): C, 72.50; H, 3.96; N, 4.23. Found (%): C, 76.47; H, 3.23; N, 4.85.

Synthesis of the manganese(III) complex: A methanol solution (4 mL) of manganese acetate tetrahydrate (12.3 mg, 0.05 mmol) was added dropwise to a mixed solution composed by triethylamine (0.5 mL) and orange yellow ethyl acetate solution (3.5 mL) of 4-hydroxy-3-[(2-hydroxy-naphthalen-1-ylmethylene)-amino]-chromen-2-one (33.1 mg, 0.1 mmol) at room temperature. The mixing solution turned to red-brown immediately and the filtrate was allowed to stand at room temperature for about three weeks. Dark reddish brown prismatical single were obtained. Elemental analysis-Anal. calcd. for C46H38MnN3O8 (%): C, 67.73; H, 4.70; N, 5.15. Found (%): C, 68.12; H, 4.55; N, 5.61.

Experimental details

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

Discussion

Coumarin derivatives are well known to possess a diverse array of pharmacological and biochemical properties and has resulted in the chemistry of coumarins becoming well established. In particular, a series of coumarin-derived Schiff bases and their complexes were found to possess significant bioactivity [5]. Furthermore, Schiff base compounds are capable of forming all kinds of stable metal complexes [6], [7], [8], which are considered more and more important because their novelty structural, topological and widely using in the fields of biochemistry [9, 10] , magnetic properties [11, 12] , photophysical properties [13, 14] , molecular recognition [15, 16] and so on.

The asymmetric unit of the title compound consists of a Mn(III) ion, two ligand units and a triethylammonium counter cation. The Mn(III) center is coordinated by a pair of N,O,O chelates from a pair of ligand units. The coordination geometry of the Mn(III) center can be described as slightly distorted octahedron. Bond lengths and all other geometric parameters are in the expected ranges.

In the title crystal structure there is one classical charge-supported N—H⋯O hydrogen bond between the ammonium group and the O5 atom (N⋯O distance <2.8 Å).

Acknowledgement

The supports by the Program for Excellent Team of Scientific Research in Lanzhou Jiaotong University (201706) are gratefully acknowledged.

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Received: 2017-6-8
Accepted: 2017-9-29
Published Online: 2017-10-16
Published in Print: 2017-11-27

©2017 Jing 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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  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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