Home Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
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Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn

  • Hai-Lin Chen , Li-Wei Pan , Yong-Ling Qin EMAIL logo , Yan-Jun Xie and Peng Zhang
Published/Copyright: December 22, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 2

Abstract

C38H48N2O26S2Zn, monoclinic, P21/c (no. 14), a = 15.7219(7) Å, b = 8.0394(4) Å, c = 17.1968(8) Å, β = 92.210(4)°, V = 2171.97(18) Å3, Z = 2, Rgt(F) = 0.0395, wRref(F2) = 0.0951, T = 293(2) K.

CCDC no.: 1879642

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:Colorless prism
Size:0.40 × 0.10 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.76 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:8830, 3813, 0.031
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2937
N(param)refined:313
Programs:Bruker programs [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
Zn11.0000000.0000000.5000000.02915(15)
S10.22333(5)0.53926(9)0.20695(4)0.02665(19)
N10.89627(14)0.4397(3)0.39539(14)0.0290(6)
H1A0.8728950.3567880.3609360.044*
H1B0.9091950.3662880.4374360.044*
O10.81607(13)0.4478(3)0.56448(12)0.0393(6)
H10.8121030.4287940.6128150.059*
O20.46416(14)0.3251(3)0.38305(14)0.0530(7)
O30.68781(13)0.5283(3)0.31862(12)0.0355(5)
O40.27956(13)0.4169(3)0.05569(12)0.0426(6)
H130.3003590.3915760.0123640.064*
O50.17162(13)0.3915(3)0.20238(13)0.0405(6)
O60.22958(13)0.6102(3)0.28481(12)0.0374(5)
O70.19513(14)0.6621(3)0.14980(12)0.0411(6)
O81.02329(13)0.2369(2)0.45895(12)0.0337(5)
O91.13537(13)0.1783(3)0.38890(13)0.0396(6)
O100.98447(14)−0.0842(3)0.38270(12)0.0410(6)
H10A0.940233−0.0693690.3535340.062*
H10B1.023722−0.0738890.3504140.062*
O110.87349(13)0.0691(3)0.50467(13)0.0381(5)
H11A0.850268−0.0053920.5317960.057*
H11B0.8437680.0666680.4623260.057*
O120.31241(14)0.3285(3)0.91059(13)0.0506(6)
H12A0.3542580.2651090.9019170.076*
H12B0.2714780.2699690.8919270.076*
O130.12753(16)0.9099(3)0.28461(14)0.0560(7)
H13A0.1480190.9929540.3095530.084*
H13B0.1636090.8377650.3006430.084*
C10.74705(19)0.4302(4)0.51697(17)0.0294(7)
C20.6729(2)0.3550(4)0.54189(19)0.0415(8)
H20.6707270.3137410.5922890.050*
C30.6040(2)0.3424(4)0.49243(19)0.0429(9)
H30.5545180.2939940.5098980.052*
C40.60531(19)0.3999(4)0.41630(17)0.0306(7)
C50.68042(18)0.4706(3)0.39292(17)0.0263(7)
C60.75214(18)0.4889(3)0.44191(17)0.0261(6)
C70.53140(19)0.3868(4)0.36301(18)0.0331(7)
C80.54401(19)0.4511(4)0.28476(18)0.0315(7)
C90.61941(19)0.5171(4)0.26920(19)0.0359(8)
H90.6253030.5595000.2193780.043*
C100.47498(19)0.4443(4)0.22402(18)0.0324(7)
C110.39245(18)0.4888(4)0.24024(18)0.0297(7)
H110.3804900.5240630.2901540.036*
C120.32762(18)0.4822(3)0.18397(17)0.0260(7)
C130.34441(18)0.4289(4)0.10891(17)0.0312(7)
C140.4271(2)0.3883(5)0.09246(19)0.0449(9)
H140.4395480.3554470.0423160.054*
C150.4910(2)0.3955(4)0.14875(19)0.0436(9)
H150.5461730.3671780.1362030.052*
C160.83206(18)0.5683(3)0.41536(17)0.0272(7)
H16A0.8189680.6369090.3700600.033*
H16B0.8556440.6396470.4562640.033*
C170.97687(18)0.5093(4)0.36714(19)0.0314(7)
H17A1.0056710.5707490.4089560.038*
H17B0.9639860.5863770.3249180.038*
C181.03512(19)0.3753(4)0.33912(17)0.0337(7)
H18A1.0048050.3123750.2986990.040*
H18B1.0832840.4281520.3155970.040*
C191.06836(19)0.2559(4)0.40006(18)0.0314(7)

Source of material

The educt sodium 5-(8-(((2-carboxyethyl)amino)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate was synthesized via a Mannich reaction. In a typical experiment a formaldehyde solution (10 mL, 37%) and sodium 2-hydroxy-5-(7-hydroxy-4-oxo-4H-chromen-3-yl)benzenesulfonate (3.56 g, 0.01 mol) were added to ethanol (200 mL, 99%) and stirred for 0.5 h at 328 K. Then, the saturated solution of 3-aminopropionic acid (1.336 g, 0.015 mol) was added to the reaction mixture. Then, hot water was added until a transparent solution was obtained. After 24 h reaction time, the mixture was filtered, and the residue was collected. Then the residue was dried at 383 K. Sodium 5-(8-(((2-carboxyethyl)amino)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate (0.874 g) was obtained. NMR spectra were recorded on a Bruker AVANCE III HD instrument. 1H-NMR (400 MHz, DMSO-d6) δ: 10.61 (s, 1H, H13), 8.37 (s, 1H, H9), 8.07 (d, J = 8.9 Hz, 1H, H3), 7.69 (d, J = 2.3 Hz, 1H, H11), 7.40 (dd, J = 8.5, 2.3 Hz, 1H, H15), 7.10 (d, J = 8.9 Hz, 1H, H2), 6.86 (d, J = 8.5 Hz, 1H, H14), 4.33 (s, 2H, H16A, H16B), 3.21 (t, J = 6.9 Hz, 2H, H17A, H17B), 2.68 (t, J = 6.9 Hz, 2H, H18A, H18B). 13C-NMR (100 MHz, DMSO-d6) δ: 174.54 (C7), 172.02 (C19), 161.58 (C1), 155.85 (C5), 153.36 (C13), 152.77 (C9), 131.47 (C15), 130.71 (C12), 128.14 (C3), 127.68 (C11), 123.28 (C10), 121.96 (C8), 116.48 (C4), 116.35 (C14), 114.42 (C2), 105.57 (C6), 42.90 (C17), 39.10 (C16), 30.36 (C18). IR (potassium bromide pellet) were recorded on a Nicolet 6700. IR (v/cm−1): 3565, 3428, 3090, 1707, 1632, 1605, 1510, 1452, 1400, 1383, 1329, 1300, 1274, 1213, 1172, 1107, 1071, 1093, 1040, 1025, 832, 811, 793, 741, 728, 645, 620, 534. ESI-MS: m/z 434.17[M–Na]−. Zincacetate dihydrate (0.0550 g, 0.25 mmol) and the aforementioned sodium salt (0.0229 g, 0.05 mmol) were added to water (10 mL) and sonicated for 10 min. The mixture was heated for 9 h at 358 K. After filtration, a transparent solution was obtained. After 2 days, colorless needle crystals of the title compound were obtained.

Experimental details

Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C). The oxygen- and nitrogen-bound H atoms were located on a difference Fourier map.

Discussion

In the past decades, the synthesis of Mannich bases that contained amino acids has been widely studied [4], [5], [6], [7], [8]. We have already synthesized two amino-acid derivatives of sodium 2-hydroxy-5-(7-hydroxy-4-oxo-4H-chromen-3-yl)benzenesulfonate by the Mannich reaction and studied their coordination behavior with metal ions [9], [10], [11]. As a continuation, we synthesized a 3-aminopropanoic acid derivative, sodium 5-(8-(((2-carboxyethyl)amino)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate. We used this compound to react with a zinc(II) acetate solution and got the title complex.

X-ray crystallographic analysis of a single crystal of the title Zn(II) complex reveals a mononuclear structure. There is one half of a Zn(II) ion, one organic ligand, two coordinated water molecules and two uncoordinated water molecules in the asymmetric unit of the title structure (cf. the figure, the asymmetric unit is labeled). Zn1, located at an inversion center, is six-coordinated with a distorted octahedral geometry by four coordinated water and two O atoms from two monodentate coordinating ligands. The Zn—O bond distances are in the range of 2.0686(19) Å and 2.133(2) Å. The carboxylate groups adopt trans conformations, with the C19—C18—C17—N1 torsion angles to be −65.0°. The nitrogen atom N1 is protonated. Adjacent ligands have intramolecular N1—H1B⋯O8 hydrogen bond of length 2.094 Å. There exist some more O—H⋯O and N—H⋯O hydrogen bonds forming a three-dimensional framework. It is obvious that the hydrogen bonds play important roles in the self-assembly and enhance stability of the resultant structure.

Acknowledgements

This work was financially supported by the Foundation of Guangxi Colleges Universities Key Laboratary of Exploitation and Utilization of Microbial and Botanical Resources (No. 2018HL005), the Education Department of Guangxi Zhuang Autonomous Region of China (No. KY2016LX290), the Foundation of Hechi University (No. XJ2016QN023).

References

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Received: 2018-07-18
Accepted: 2018-11-18
Published Online: 2018-12-22
Published in Print: 2019-03-26

©2019 Hai-Lin Chen et al., published by De Gruyter, Berlin/Boston

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

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  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
https://doi.org/10.1515/ncrs-2018-0250
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
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