Startseite Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
Artikel Open Access

Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n

  • Junshan Sun EMAIL logo
Veröffentlicht/Copyright: 15. Dezember 2018

Abstract

C12H14FN3S2Sn, orthorhombic, Pbca (no. 61), a = 12.954(3) Å, b = 11.494(3) Å, c = 20.825(5) Å, V = 3100.7(13) Å3, Z = 8, Rgt(F) = 0.0274, wRref(F2) = 0.0658, T = 298(2) K.

CCDC no.: 1879776

The crystal structure is shown in the figure (The asymmetric unit is labelled plus the symmetry related N2a atom; a = −x, −0.5 + y, 0.5 − z). 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 block
Size:0.24 × 0.20 × 0.17 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.92 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:13303, 2730, 0.036
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2017
N(param)refined:172
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
Sn10.06879(2)0.44181(2)0.24525(2)0.04387(10)
C100.1255(4)0.5618(3)0.31421(19)0.0621(11)
H10A0.1958370.5432360.3243770.093*
H10B0.1219370.6391950.2970150.093*
H10C0.0842310.5572550.3524350.093*
S10.16267(8)0.75847(8)0.08153(5)0.0506(3)
S20.16415(9)0.52602(8)0.14606(5)0.0559(3)
N30.0709(2)0.9768(2)0.09061(14)0.0451(7)
C20.0814(3)0.8639(3)0.11276(17)0.0411(8)
N10.0505(2)0.7144(2)0.17868(14)0.0480(8)
N20.0293(2)0.8285(2)0.16243(14)0.0447(7)
C10.1175(3)0.6669(3)0.14093(16)0.0410(8)
C11−0.0837(3)0.4526(4)0.2100(2)0.0664(12)
H11A−0.0952350.3914490.1793890.100*
H11B−0.1314730.4446520.2449360.100*
H11C−0.0937680.5265920.1895160.100*
C120.1509(3)0.2830(3)0.2351(2)0.0611(11)
H12A0.2185920.2912250.2532090.092*
H12B0.1144630.2220680.2570050.092*
H12C0.1566660.2638320.1903250.092*
F10.1213(3)1.4589(2)−0.05275(16)0.1110(11)
C30.1212(3)1.0087(3)0.04115(18)0.0481(9)
H30.1620380.9540110.0202280.058*
C40.1179(3)1.1263(3)0.01579(18)0.0483(10)
C70.1195(4)1.3486(4)−0.0306(2)0.0726(14)
C50.0610(3)1.2126(3)0.0462(2)0.0607(11)
H50.0221201.1945760.0823890.073*
C90.1745(4)1.1541(4)−0.03873(19)0.0632(12)
H90.2122561.096691−0.0596670.076*
C60.0619(4)1.3252(4)0.0228(2)0.0754(14)
H60.0241521.3835440.0428710.090*
C80.1748(4)1.2668(4)−0.0620(2)0.0728(14)
H80.2123461.285897−0.0986060.087*

Source of materials

The ligand was prepared by 4-fluorobenzaldehyde and 5-amino-1,3,4-thiadiazole-2-thiol in the refluxing in solvent of ethanol for 2 h. The yellow precipitation was obtained by the filtering. The title complex was synthesized by reacting the aforementioned ligand and trimethyltin chloride, in the presence of sodium ethoxide, as the dehydrogenation reagent, while heating for 4 h at 313 K. The mixture was filtered and the filtration was distilled. The product was recrystallized in hexane/dichloromethane with a ratio of 2:1. The colorless block crystals were obtained by evaporation. Yield: 69% (based on Sn element), and elemental analysis: calc. for C12H14FN3S2Sn: C 35.85, H 3.51, N 10.45; found: C 35.61, H 3.29, N 10.13. PERKIN ELMER MODEL 2400 SERIES II.

Experimental details

Hydrogen atoms were assigned with isotropic displacement factors Uiso(H) = 1.5 times Ueq (C, methyl) and Uiso(H) = 1.2 times Ueq (C, methyne and benzene ring). All the H atoms were refined as riding on their parent atom.

Comment

Organotin(IV) complexes have been causing more and more attention for their industrial applications and potential biological activities [3], [4], [5]. Especially many varieties of organotin(IV) complexes have been synthesized and studied in the context of their antitumour potential [6]. Heterocyclic thiones that contain at least one deprotonated heterocyclic thioamide group (N—C—S) have been studied for their versatile coordination modes and biological activities [7]. Also, Schiff base derived from various heterocycles were reported to possess cytotoxic, anticonvulsant, antiproliferative, anticancer and antifungal activities. So we are interesting to assemble the Schiff base group and the heterocyclic thioamide (N—C—S) to study the property of organotin(IV) complexes.

The title complex is shown in the figure. Each tin(IV) is coordinated by three methyl groups and two nitrogen atoms from two crystallographically dependent organic ligands. Thus the coordination is trigonal bipyramidal. The bond length of S-Sn 2.5942(11) Å, is a little bit longer than the sum of the covalent radii of tin and sulfur (2.42 Å). The Sn atom is 0.15 Å shifted out of the plane, formed by the three C methyl atoms (C10, C11, C12). All bond lengths are in the expected ranges.

Acknowledgements

Financial support from the Shandong Provincial Higher Education Research and Development Program Project (No. J18KB049) and Talent Foundation of Taishan University (No. Y2015–1–002) are gratefully acknowledged.

References

1. Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA (2004).Suche in Google Scholar

2. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

3. Ma, C. L.; Zhang, J. H.; Tian, G. R.; Zhang, R. F.: Syntheses, crystal structures and coordination modes of tri- and di-organotin derivatives with 2-mercapto-4-methylpyrimidine. J. Organomet. Chem. 690 (2005) 519–533.10.1016/j.jorganchem.2004.10.020Suche in Google Scholar

4. Duboy, S. K.; Roy, U.: Biodegradation of tributyltins (organotins) by marine bacteria. Appl. Organomet. Chem. 17 (2003) 3–8.10.1002/aoc.394Suche in Google Scholar

5. Ma, C. L.; Shi, Y.; Zhang, R. F.; Jiang, Q.: Syntheses, characterization and crystal structures of diorganotin compounds with 2-mercaptopyrimidine and 4-amino-2-mercaptopyrimidine. Polyhedron 24 (2005) 1109–1116.10.1016/j.poly.2004.11.029Suche in Google Scholar

6. Gielen, M.: Organotin compounds and their therapeutic potential: a report from the organometallic chemistry department of the free university of brussels. Appl. Organomet. Chem. 16 (2002) 481–494.10.1002/aoc.331Suche in Google Scholar

7. Gielen, M.; Vornefeld, M.; Preut, H.: The determination of organotin compounds in fruit juices using gas chromatography-atomic absorption spectrometry. Appl. Organomet. Chem. 6 (1992) 579–585.10.1002/aoc.590060704Suche in Google Scholar

Received: 2018-09-30
Accepted: 2018-11-21
Published Online: 2018-12-15
Published in Print: 2019-03-26

©2019 Junshan Sun, published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  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
Heruntergeladen am 22.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0407/html
Button zum nach oben scrollen