Home Physical Sciences Crystal structure of (E)-1-(thiophen-2-yl)-N-(5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine, C25H19N3S3Sn
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Crystal structure of (E)-1-(thiophen-2-yl)-N-(5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine, C25H19N3S3Sn

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Published/Copyright: February 14, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 3

Abstract

C25H19N3S3Sn, monoclinic, P21/n (no. 14), a = 14.347(4) Å, b = 9.908(3) Å, c = 17.834(5) Å, V = 2405.6(11) Å3, Z = 4, Rgt(F) = 0.0287, wRref(F2) = 0.0777, T = 298(2) K.

CCDC no.: 1890996

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.

Source of material

The thio-ligand was prepared by thiophene-2-carbaldehyde and 5-amino-1,3,4-thiadiazole-2-thiol in the refluxing in 80 °C in solvent of ethanol for 2 h. The yellow precipitation was obtained by filtering. The title complex was synthesized by the thio-ligand and triphenyltin chloride, in the presence of sodium ethoxide, as the dehydrogenation reagent, heating for 4 h at 313 K. The mixture was filtered and the filtration was distilled by rotary evaporator. The product was recrystallized in hexane/dichloromethane with the ratio 1:1. The colorless block crystals were obtained by evaporation in air.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.68 × 0.52 × 0.49 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.34 mm−1
Diffractometer, scan mode:APEX2, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:12136, 4237, 0.041
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3180
N(param)refined:289
Programs:Bruker [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
Sn11.19065(2)1.43448(2)0.49628(2)0.04420(10)
S11.54083(7)1.34028(10)0.57363(6)0.0570(3)
S21.32957(7)1.32324(11)0.46818(6)0.0623(3)
S31.84360(8)1.52684(12)0.84447(7)0.0698(3)
N11.4027(2)1.4777(3)0.5971(2)0.0541(8)
N21.4853(2)1.5142(3)0.65729(19)0.0561(8)
N31.6518(2)1.4678(3)0.71334(19)0.0568(8)
C11.4191(3)1.3891(4)0.5488(2)0.0505(9)
C21.5627(3)1.4492(4)0.6549(2)0.0520(9)
C31.7213(3)1.3843(4)0.7196(2)0.0593(10)
H31.7103151.3130700.6839390.071*
C41.8151(3)1.3945(4)0.7786(2)0.0517(9)
C51.8925(3)1.3085(4)0.7921(2)0.0586(10)
H51.8911521.2303560.7629460.070*
C61.9736(3)1.3492(5)0.8537(2)0.0643(11)
H62.0323141.3013610.8704500.077*
C71.9582(3)1.4649(5)0.8866(2)0.0678(12)
H72.0055021.5069060.9281000.081*
C81.1875(2)1.6483(4)0.47801(19)0.0435(8)
C91.2547(3)1.7355(4)0.5253(2)0.0569(10)
H91.3063511.7015850.5668580.068*
C101.2472(3)1.8721(4)0.5124(3)0.0692(12)
H101.2936171.9295310.5452080.083*
C111.1720(3)1.9245(4)0.4516(3)0.0650(11)
H111.1675692.0171250.4427710.078*
C121.1036(3)1.8401(4)0.4043(3)0.0668(11)
H121.0517761.8752780.3633430.080*
C131.1108(3)1.7017(4)0.4169(2)0.0582(10)
H131.0639941.6445660.3841140.070*
C141.0765(2)1.3368(3)0.40645(19)0.0422(8)
C151.0647(3)1.3528(4)0.3265(2)0.0579(10)
H151.1069541.4094940.3109770.069*
C160.9913(3)1.2858(4)0.2699(2)0.0651(11)
H160.9840381.2984560.2166900.078*
C170.9292(3)1.2008(4)0.2915(2)0.0613(11)
H170.8803631.1546790.2531190.074*
C180.9392(3)1.1842(4)0.3694(2)0.0614(10)
H180.8967131.1270500.3843550.074*
C191.0121(3)1.2518(4)0.4262(2)0.0517(9)
H191.0179001.2396420.4792140.062*
C201.1837(2)1.3584(4)0.60551(19)0.0423(8)
C211.1569(3)1.4369(4)0.6591(2)0.0552(10)
H211.1481311.5292170.6503980.066*
C221.1429(3)1.3806(5)0.7255(2)0.0715(12)
H221.1248991.4349270.7611690.086*
C231.1553(3)1.2456(5)0.7387(2)0.0755(13)
H231.1449141.2075120.7830820.091*
C241.1829(3)1.1659(5)0.6870(3)0.0759(13)
H241.1918971.0737230.6962560.091*
C251.1973(3)1.2225(4)0.6212(2)0.0610(10)
H251.2166631.1676670.5864330.073*

Yield: 83% (based on Sn), and elemental analysis: calc. for C25H19N3S3Sn: C 52.10, H 3.32, N 7.29%; found: C 52.31, H 3.24, N 7.15%. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.

Experimental details

All hydrogen atomic positions were taken from a difference Fourier map. Hydrogen atoms were assigned with common isotropic displacement factors Uiso(H) = 1.2 times Ueq (C, phenyl ring and thiophene ring). All the H atoms were refined as riding on their parent atom.

Comment

Organotin(IV) complexes, the bioactive organometallics, have gained widely attention due to their structural diversity and effective anticancer activity [3], [4], [5]. Especially many varieties of organotin(IV) complexes with the heteroatoms of N, O and S are under investigation [6], [7], [8]. The heterocyclic thiones that contain at least one deprotonated heterocyclic thioamide group (N—C—S) have been subject for their versatile coordination modes and biological activities. Schiff base derived from various heterocycles were reported to possess biological activity [9]. So we are interested to assemble the Schiff base group and the heterocyclic thioamide group (N—C—S) to study the properties of a corresponding organotin(IV) complex.

The aforementioned thio-ligand was reacted with the triphenyltin chloride to give the title compound (see the figure). The bond length of S—Sn 2.4633(11) Å, which is close to the covalent radii of tin and sulfur atoms (2.42 Å) [10]. The environment of Sn atom is a distorted tetrahedron. The angles of C—Sn—S and C—Sn—C are from 97.07(9) to 119.10(13)°, showing architecture of the Sn atom with surrounding atoms is seriously distorted from the tetrahedron geometry.

Geometric parameters in the thio-ligand are as expected [11], [12] .

Funding source: Shandong Provincial Higher Education Research and Development Program Project

Award Identifier / Grant number: J18KB049

Funding source: Talent Foundation of Taishan University

Award Identifier / Grant number: Y2015−1−002

Funding statement: 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

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Received: 2018-11-07
Accepted: 2019-01-15
Published Online: 2019-02-14
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.

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  72. Crystal structure of N-methylanilinium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate monohydrate, C22H21NO8S
  73. Crystal structure of methyl 4-acetoxybenzoate, C10H10O4
  74. Crystal structure of catena-poly[(bis(μ-1,1′-[(5-methoxy-2,4,6-trimethyl-1,3-phenylene)bis(methylene)]bis(1H-1,2,4-triazole)-κ2N:N′)-bis(isothiocyanato-κN)manganese(II)], C34H40MnN14O2S2
  75. Crystal structure of N-(2-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
https://doi.org/10.1515/ncrs-2018-0490
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of poly[aqua-μ2-4,4′-bis(pyrid-4-yl)biphenyl-κ2N:N′)-μ4-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-κ4O:O′:O′′:O′′′)manganese(II)], C52H40N2O10Mn2
  3. Crystal structure of bis[2-(((3-aminopropyl)imino)methyl)-4-nitro-phenolato-κ3N,N′,O]nickel(II), C20H24N6NiO6
  4. Synthesis and crystal structure of bis{2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl) phenolato-κ2N,O}cobalt(II) — ethanol (1/1), C34H36CoN4O5
  5. Crystal structure of 1-(4-{2,5-dichloro-3-hydroxy-4-[4-(1-methoxyimino-ethyl)-phenylamino]-6-methyl-phenylamino}-phenyl)-ethanone O-methyl-oxime, C24H22Cl2N4O4
  6. The pseudosymmetric crystal structure of 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane dimethyl carbonate (2/3), C21H30N24O33
  7. Crystal structure of (1,4-diazepane)4CuII2(μ-Cl)10CuI6, C20H48Cl10Cu8N8
  8. Crystal structure of methyl 2,7,7-trimethyl-4-(3-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H23NO3S
  9. Crystal structure of methyl 2-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H13N3O2
  10. Crystal structure of (1S,3aR,3bR,10aR,10bR,12aR)-8-amino-3a,3b,6,6,10a-pentamethyl-1-((S)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-cyclopenta[7,8]phenanthro[2,3-d]thiazol-12-ol – a panaxadiol dervative, C31H50N2O2S
  11. Crystal structure of bis[(((4-fluorophenyl)amino)methyl)triphenylphosphonium] tetrachloridocobaltate(II), C50H44Cl4CoF2N2P2
  12. Crystal structure of 5,4′-dihydroxy-7,3′-dimethoxyflavanone, C17H16O6
  13. Crystal structure of 3-methyl-cyclobis(1-(1,1′-ferrocenylmethyl)-4-butyl-1H-1,2,3-triazole) tetrafluoroborate, C21H25FeN6⋅BF4
  14. Crystal structure of 3-(2-diethylaminoethyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C14H19N3OS
  15. Crystal structure of 2-(bis(3,5-dimethylphenyl) ((methyldiphenylsilyl)oxy)methyl) pyrrolidine, C34H39NOSi
  16. The crystal structure of 1,4-dinitro-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O12
  17. Crystal structure of rac-3,6-dimethyl-5-(prop-1-en-2-yl)-6-vinyl-1,4,5,6-tetrahydro-2H-indol-2-one, C15H19NO
  18. Crystal structure of (Cu0.51In0.49)tet[Cr1.74In0.26]octSe4 selenospinel, Cu0.51In0.75Cr1.74Se4
  19. Crystal structure of 7-hydroxy-5-methoxy-4,6-dimethylisobenzofuran-1(3H)-one, C11H12O4
  20. Crystal structure of trans-tetrakis(acetonitrile-κN)bis(triphenylphosphine-κP)ruthenium(II) dihexafluorophosphate - dichloroform (1/2), C46H44Cl6F12N4P4Ru
  21. Crystal structure of 2-((4-nitrophenyl)thio)ethan-1-ol, C8H9NO3S
  22. Crystal structure of diaqua-dichlorido-bis(μ3-6,6′-(hydrazine-1,2-diylidenebis(methanylylidene))bis(2-methoxyphenolato)κ6O,N:N′,O′,O′:O′′)trizinc(II) - ethanol (1/2), C36H44Cl2N4O12Zn3
  23. Crystal structure of the co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-chlorobenzoic acid (2/1), C35H25ClO10S4
  24. The crystal structure of 4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol, C15H11ClFN3O2
  25. Crystal structure of ethyl (E)-1-(3-ethoxy-3-oxoprop-1-en-1-yl)-2-(4-nitrophenyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate, C23H23N3O6
  26. Crystal structure of (E)-2-(4-cyanophenyl)ethenesulfonyl fluoride, C9H6FNO2S
  27. Crystal structure of bis(4-bromo-2-(((3-chloropropyl)imino)methyl)phenolato-κ2N,O)-oxidovanadium(IV), C20H20Br2Cl2N2O3V
  28. The crystal structure of 1,1,1,3,3,3-hexaphenyldistannoxane – 2,2′-bipyridine (1/1), C46H38N2OSn2
  29. Crystal structure of coordination polymer catena-poly[diaqua-(2,6-dichloropyridine-4-carboxyliato-κ2O,O′)-bis(μ2-2,6-dichloropyridine-4-carboxyliato-κ2O:O′)terbium(III), C18H10Cl6N3O8Tb
  30. The crystal structure of 4-((2-(4,5-dihydro-1,5-diphenyl-1H-pyrazol-3-yl)anthracen-10-yl) methyl)morpholine, C34H31N3O
  31. The crystal structure of bis(N,N-dimethylformamide-κO)-tetrakis(9H-xanthene-9-carboxylic-carboxylate-κ2O:O′)dicopper(II) - acetonitrile (1/2), C66H56Cu2N4O14
  32. Crystal structure of trans-dichlorido-(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)-(5-methyl-3,4-dihydro-2H-pyrrole-κN)palladium(II), C25H31Cl2N3OPd
  33. Crystal structure of 8,8′-di-p-tolyl-8′H-7,8′-biacenaphtho[1,2-d]imidazole, C40H26N4
  34. The crystal structure of 3-amino-(2,4-dioxopent-3-yl)-4,5-dihydro-1,2,4-triazinium nitrate, C8H13N5O5
  35. Crystal structure of 4,4′,5,5′-tetraphenyl-2,2′-di-p-tolyl-2′H-1,2′-biimidazole, C44H34N4
  36. Halogen bonds in the crystal structure of 2-bromo-1,10-phenanthroline – 1,4-diiodotetrafluorobenzene (2/1), C30H14Br2F4I2N4
  37. Crystal structure of tris(1-phenyl-1,2-propanedione-2-oximato-κ2N,O)cobalt(III), C27H24N3O6Co
  38. Crystal structure of chlorido-(6,6′-((1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(3-methoxyphenolato)-κ4O,N,N′,O′)iron(III), C22H18ClN2FeO4
  39. Crystal structure of bis(μ2-1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-olato-κ3O,O′:O′)-bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-olato-κ2O,O)-bis(ethyl acetate-κO)dicadmium(II), C88H64Cl4N8O12S4Cd2
  40. Crystal structure of catena-poly[dichlorido-(μ2-3-(2-pyridyl)-4-(4-pyridyl)-5-(3-pyridyl)-1,2,4-triazole-κ2N:N′)] copper(II), C17H12N6Cl2Cu
  41. Crystal structure of dichlorido-([2,2′:6′,2′′-terpyridine]-4′-carboxylic acid-κ3N,N′,N′′)copper(II) monohydrate, C16H13Cl2CuN3O3
  42. Crystal structure of triethylammonium(5-carboxypyridine-2-thiolato-κ2N,S)-bis(dimethylsulfoxide-κ1S)-(6-sulfidonicotinato-κ2N,S)ruthenium(II) trihydrate, C22H41N3O9RuS4
  43. The crystal structure of poly[(μ5-2,5-dicarboxy-benzoato-κ4O:O:O′:O′′,O′′′)silver(I)], C9H5AgO6
  44. Crystal structure of (E)-1-(thiophen-2-yl)-N-(5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine, C25H19N3S3Sn
  45. Crystal structure of diaqua-bis(3,5-dichloroisonicotinato-κ1O)-bis(1,3-di(pyridin-4-yl)propane-κ1N)cobalt(II), C38H36Cl4N6O6Co
  46. Crystal structure of dodecaaqua-bis(μ2-4,4′-bipyridine-κ2N:N′)-bis(4,4′-((5-carboxylato-1,3-phenylene)bis(oxy))dibenzoato-κ1O)tricopper(II) - water (1/4), C62H70Cu3N4O32
  47. Crystal structure of bis(5-methoxy-2-(((2-oxidoethyl)imino)methyl)phenolate-κ3O,N,O′)manganes(IV), C20H22N2O6Mn
  48. Crystal structure of tetramethylammonium (2-(3-ethoxy-2-oxidobenzylidene)-1-(2-hydroxybenzoyl)hydrazin-1-ido-κ3N,N′,O)cobalt(III), C36H40N5O8Co
  49. Crystal structure of 6-cyclohexyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl nitrate, C20H23O3N2Bi
  50. Crystal structure of (E)-N-((2S,3S,4R,10R,13S, 17S)-17-(1-(dimethylamino) ethyl)-2,4-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide, C24H48N2O3
  51. Crystal structure of (E)-2-((4-chlorophenyl)(phenyl)methylene)hydrazine-1-carbothioamide, C14H12ClN3S
  52. Crystal structure of 1-benzyl-3-cyano-6-phenyl-1,2-dihydropyridine, C19H16N2
  53. Isolation and crystal structure of 4-((2-(methoxycarbonyl)phenyl)amino)-2-methyl-4-oxobutanoic acid from Delphinium Grandiflorum, C13H15N1O5
  54. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)nickel(II), C16H22O10Ni
  55. Crystal structure of ajacisine D monohydrate, C30H44N2O9
  56. The crystal structure of (E)-4-(1-(2-aminophenylimino)ethyl)benzene-1,3-diol, C14H14N2O2
  57. Crystal structure of poly[(μ4-(4H-1,2,4-triazol-4-yl)phenyl)acetato-κ4N,N′,O,O′)(formiato-κ1O)cobalt(II)], C11H9CoN3O4
  58. The crystal structure of bis tetrabutylammonium bis(μ3-2,2,2-tri(hydroxymethyl)ethyl-4-((3-methoxy-3-oxopropyl)amino)-4-oxobutanoato)-(μ6-oxido)-hexakis(μ2-oxido)-hexaoxido-hexavanadium(V), C58H112N4O29V6
  59. Crystal structure of (N-benzylpropane-1,3-diamine-κ2N, N′)(2,2′-bipyridine-κ2N,N′)platinum(II) chloride, C20H24Cl2N4Pt
  60. Crystal structure of 5-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-N-phenyl-2-amine, C23H16ClN5O
  61. Crystal structure of poly-[(μ2(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N: O:O′)(μ2-4,4′-bipyridine-κ2N:N′)copper(II)], C18H14CuN4O6S
  62. Crystal structure of poly-[(μ2-(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N:O:O′)(μ2-4,4′-bipyridine-κ2N:N′) nickel(II)], C18H14NiN4O6S
  63. Crystal structure of N-((3R,10S,13S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-N-methylbenzamide, C31H48N2O
  64. The crystal structure of dichloroido(1,3-bis(2,6-dimethyl-phenyl)-1H-3l4-imidazol-2-yl)(2-methyl-4,5-dihydrooxazol-κN)palladium(IV)-water (1/1), C23H29Cl2N3O2Pd
  65. Crystal structure of catena-poly[dibromido-{μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O}zinc(II)], C34H32Br4N8O2Zn2
  66. Crystal structure of diaqua-dichlorido-bis(μ2-2-(((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)dicobalt(II), C36H36Cl2N6O6Co2
  67. Crystal structure of catena-poly[diaqua-(μ2-1,2-bis(4-pyridinyl)ethyane-κ2N:N′)-(μ2–pyridazine-4,5-dicarboxylato-κ2O:O′)]dizinc(II) dihydrate, C12H12ZnN3O6
  68. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro)diazene oxide, C12H6Cl2N4O5
  69. Crystal structure of 2-isopropylthioxanthone, C16H14OS
  70. Crystal structure of methyl 2-(4-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C19H17N5O2
  71. Crystal structure of 4,4-dimethyl-2-(trifluoromethyl)-4,5-dihydro-1H-imidazole, C6H9F3N2
  72. Crystal structure of N-methylanilinium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate monohydrate, C22H21NO8S
  73. Crystal structure of methyl 4-acetoxybenzoate, C10H10O4
  74. Crystal structure of catena-poly[(bis(μ-1,1′-[(5-methoxy-2,4,6-trimethyl-1,3-phenylene)bis(methylene)]bis(1H-1,2,4-triazole)-κ2N:N′)-bis(isothiocyanato-κN)manganese(II)], C34H40MnN14O2S2
  75. Crystal structure of N-(2-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
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