Home Physical Sciences The crystal structure of bis{tetrakis(n-butyl)(μ-hydroxy)(2,3,5,6-tetrafluorobenzoate) (μ 3 -oxo)ditin(IV)}
Article Open Access

The crystal structure of bis{tetrakis(n-butyl)(μ-hydroxy)(2,3,5,6-tetrafluorobenzoate) (μ 3 -oxo)ditin(IV)}

  • Lifang He , Biao Li , Xinbo Hou , Xiongwei Wu , Yihu Hou , Xiaoming Zhu ORCID logo and Fuxing Zhang ORCID logo EMAIL logo
Published/Copyright: May 23, 2025

Abstract

C46H76F8O8Sn4, monoclinic, P21/n (no. 14), a = 13.2408(8) Å, b = 14.3875(9) Å, c = 15.9892(10) Å, β = 104.2490(10)°, V = 2952.3(3) Å3, Z = 2, Rgt (F) = 0.0434, wRref (F 2) = 0.1148, T = 296 (2) K.

CCDC no.: 2278990

The molecular structure is shown in the figure. Table 1 contains the crystallographic data and the list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Block colorless
Size: 0.26 × 0.24 × 0.21 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.74 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω scans
θ max, completeness: 25.8°, 100 %
N(hkl)measured, N(hkl)unique, R int: 15630, 5651, 0.021
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 4340
N(param)refined: 312
Programs: Bruker, 1 SHELX, 2 , 3 WinGX 4

1 Source of material

All chemicals were purchased from commercial sources and used as received without further purification. An oven-dried flask was charged with dibutylstannanone (2 mmol), 2,3,5,6-tetrafluorobenzoic acid (1 mmol) and CH3CH2OH (25 mL). Then the mixture was refluxed with agitating for 12 h. Finally, the title crystal was precipitated by controlling solvent volatilization.

2 Experimental details

All H-atoms bonded to C atoms were placed geometrically and refined using a riding model with common isotropic displacement factors U iso(H) = 1.2 or 1.5 U eq(parent C-atom).

3 Comment

Organotin carboxylates have indeed garnered significant attention in both academic and industrial research due to their diverse structural properties and notable biological activities. 5 , 6 , 7 , 8 With increasing understanding of the structure-property relationships of organotin carboxylates, researchers are actively designing and developing novel compounds to expand their application scope. 9 , 10

In the molecular structure (Figure), it displays a typical ladder structure. 11 , 12 It consists of Sn4O4 ladders with an additional oxygen atom from the ligand coordinating to the tin atom. The Sn(V) ion is five-coordinated by one oxygen atom of one carboxyl group and two carbon atoms of two n-butyl groups and two oxygen atoms from the ladder core (see the figure). Bond lengths and angles are all in the expected ranges. 13 , 14 , 15 The C–Sn–C angles, C–Sn–O angles, O–Sn–O angles and O–Sn–O angles are ranging from 128.3(3)°, to 132.6(8)°, 191.4(12)°, to 116.8(2)°, 73.18(14)°, to 154.56(14)°, and 102.03(16)°, to 142.62(16)°, respectively. The bond lengths of Sn–C and Sn–O are ranging from 2.098(7) to 2.151(8)°, and 2.011(3)°, to 2.209(4)°, respectively.


Corresponding author: Fuxing Zhang, Key Laboratory of Organometallic New Materials (Hengyang Normal University), College of Hunan Province, Hunan Provincial Key Laboratory of Functional Metal-Organic Compounds, School of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China, E-mail:

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by the Research Special Project University (No. KYZX21008, No. KYZX21009), Hunan Provincial Natural Science Foundation of China (No. 2024JJ5057), Scientific Research Projects of Education Department of Hunan Province (No. 23B0669).

  3. Conflict of interest: The authors declare no conflicts of interest regarding this article.

References

1. Bruker SAINT, APEX2 and SADABS; Bruker AXS Inc.: Madison, WI, USA, 2012.Search in Google Scholar

2. Sheldrick, G. M. SHELXTL – Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Farrugia, L. J. WinGX and Ortep for Windows: An Update. J. Appl. Crystallogr. 2012, 45, 849–854; https://doi.org/10.1107/s0021889812029111.Search in Google Scholar

5. Du, X.-M.; Ma, J.-W.; Li, Q.-L.; Cui, Y.; Ma, C.-L. Triphenylamine-Appended Tri-Organotin Complexes: Synthesis, Anticancer Activities, and Targeted Research. Appl. Organomet. Chem. 2024, 38, e7522; https://doi.org/10.1002/aoc.7522.Search in Google Scholar

6. Crowe, A. J. Organotin Compounds in Agriculture Since 1980. Part I. Fungicidal, Bactericidal and Herbicidal Properties. Appl. Organomet. Chem. 1987, 1, 143–155; https://doi.org/10.1002/aoc.590010206.Search in Google Scholar

7. Tiekink, E. R. T. Structural Chemistry of Organotin Carboxylates: A Review of the Crystallographic Literature. Appl. Organomet. Chem. 1991, 5, 1–23; https://doi.org/10.1002/aoc.590050102.Search in Google Scholar

8. Pruchnik, H.; Lis, T.; Latocha, M.; Zielińska, A.; Ułaszewski, S.; Pelińska, I.; Pruchnik, F. P. Butyltin(IV) 2-Sulfobenzoates: Synthesis, Structural Characterization and their Cytostatic and Antibacterial Activities. J. Inorg. Biochem. 2012, 111, 25–32; https://doi.org/10.1016/j.jinorgbio.2012.02.024.Search in Google Scholar PubMed

9. Xu, J.; Wang, T.; Fang, Z.; Cai, X.; Dai, W.; Wang, J.; Tian, X.; Xu, X.; Zhang, Q.; Tian, Y. Highly Hydrophilic Quaternary Ammonium Salt Containing Organotin (IV) Carboxylate for Visualization of Antibacterial Action and Multi-Photon Absorption Activity. Dyes Pigm. 2022, 200, 110186; https://doi.org/10.1016/j.dyepig.2022.110186.Search in Google Scholar

10. Annuar, S. N. S.; Kamaludin, N. F.; Awang, N.; Chan, K. M. Cellular Basis of Organotin(IV) Derivatives as Anticancer Metallodrugs: A Review. Front. Chem. 2021, 9, 657599; https://doi.org/10.3389/fchem.2021.657599.Search in Google Scholar PubMed PubMed Central

11. Sun, J. Crystal Structure of Bis(μ3-oxido)-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O′)- bis(2,3,4,5-tetrafluorobenzoato-κO)-oktakis(3-chlorobenzyl- κC)tetratin(IV), C84H52C18F16O10Sn4. Z. Kristallogr. NCS. 2020, 235, 291–292; https://doi.org/10.1515/ncrs-2019-0613.Search in Google Scholar

12. Lei, T.; Wang, G.-Y.; Li, Z.-H.; Lin, S.; Fang, X.-N. Crystal Structure of Bis(tetrakis(trimethylsilylmethyl)(μ-hydroxy)(p-nitro- benzoato)(μ3-oxo)ditin(IV)), [Sn2O(OH)(NO2C6H4COO){(CH3)3SiCH2}4]2. Z. Kristallogr. NCS 2006, 221, 492–494; https://doi.org/10.1524/ncrs.2006.0169.Search in Google Scholar

13. Wang, Q.-F.; Ma, C.-L.; He, G.-F.; Li, Z. Synthesis and Characterization of New Tin Derivatives Derived from 3,5,6-Trichlorosalicylic Acid: Cage, Chain and Ladder X-Ray Crystal Structures. Polyhedron 2013, 49, 177–182; https://doi.org/10.1016/j.poly.2012.09.057.Search in Google Scholar

14. Xiao, X.; Han, X.; Mei, Z.; Zhu, D.; Shao, K.; Liang, J.; Tian, M.; Xu, L. Organotin(IV) Carboxylates Based on Amide Carboxylic Acids: Syntheses, Crystal Structures and Characterizations. Appl. Organomet. Chem. 2013, 729, 28–39; https://doi.org/10.1016/j.jorganchem.2013.01.017.Search in Google Scholar

15. Zhao, Y.; Huang, X.; Si, Y.; Zheng, L.; Chen, H.; Jun, Z.; Luo, F.; Zhang, J.; Chen, P.; Peng, X. Additive-Assisted Forming High-Quality Thin Films of Sn -Oxo Cluster for Nanopatterning. ACS Appl. Mater.Interfaces 2024, 16, 41659; https://doi.org/10.1021/acsami.4c06230.Search in Google Scholar PubMed

Received: 2025-03-16
Accepted: 2025-05-13
Published Online: 2025-05-23
Published in Print: 2025-08-26

© 2025 the author(s), published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Hydrothermal synthesis, crystal structure of [K3:N1:N2:N4-3-(pyridin-2-yl)-1,2,4-triazole] binuclear Ni(II) complex[Ni2(C7H5N4)2(C7H4ClO2)2]
  4. The crystal structure of di(thiocyanato-κ1N)-bis(methanol)-di(1,3-bis((pyridin-4-ylthio)methyl)benzene)-iron(II), C40H40FeN6O2S6
  5. Crystal structure of poly[(μ 3-3,3″,5,5″-tetrafluoro-(1,1′:4′,1″-terphenyl)-4,4″-dicarboxylate-κ 3 O,O:O″)-(μ 4-3,3″,5,5″-tetrafluoro-(1,1′:4′,1″-terphenyl)-4,4″-dicarboxylate-κ 4 O,O,O,O‴)-dicadmium(II)]dimethylformamide solvate, C47H30Cd2F8N3O12
  6. The crystal structure of a 3d-4f complex based on 2-(benzo[d]thiazol-2-yl)-6-methoxyphenol C31H27N4O13S2CoEr
  7. Crystal structure of poly[(μ 2-1,4-bis(imidazol-1-yl)benzene-k 2 N:N′)(μ 4-biphenyl-3,3′,5,5′-tetracarboxylic-k 4 O,O,O,O)dizinc(II)] dihydrate, C40H28Zn2N8O9
  8. The crystal structure of 4-(bis(2-chloroethyl)amino)-2-hydroxybenzaldehyde, C11H13Cl2NO2
  9. Synthesis and crystal structure of-(10S,13S,16R,Z) −17-ethylidene-16-hydroxy-10,13-dimethylhexadecahydro-3 H-cyclopenta[α]phenanthren-3-one, C21H32O2
  10. The crystal structure of catena-((μ 2-4,4′-bipyridine-κ 2 N:N′)-bis(4-fluorobenzoato-κ1O)-copper(II)), C24H16F2N2O4Cu
  11. Crystal structure of catena-poly[(ethylenediamine-κ2 N,N′)-μ-tetraoxomolybdato(VI) zinc(II)], C2H8MoN2O4Zn
  12. The crystal structure of 4-chloro-1H-pyrazole-3-carboxylic acid, C4H3ClN2O2
  13. The crystal structure of bepotastine besilate, C27H31ClN2O6S
  14. The crystal structure of (η 6-p-cymene)benzyldiphenylphosphine-diiodido-ruthenium(II) dichloromethane solvate
  15. The crystal structure of poly[(μ 2-1-(1-imidazolyl)-4- (imidazol-1′-yl-methyl)benzene κ 2 N:N′)-(μ 2-3-nitrobenzene -1,2-dicarboxylato-k4,O,O′:O′′,O′′′]zinc(II)-κ 2, C21H15N5O6Zn
  16. The crystal structure of (2R,4S)-5-([1,1′-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methyl pentanoic acid, C23H29NO4
  17. The crystal strucure of [2,2′-{1,2-phenylenebis [(azanylylidene)methanylylidene]}bis(4-fluorophenolato)-κ4 N,N′,O,O′] nickel(II) N, N-dimethylformamide solvate, C23H19F2N3NiO3
  18. The structure of (E)-6-(cyclopropylmethyl)-11-(2,2-difluoropropylidene)-2-methyl-6, 11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C21H21F2NO2S
  19. Crystal structure of catena-poly[(μ 2-(2-(1H-imidazol-1-ylmethyl)benzyl)-1H-imidazole κ2N:N′)- (μ 2-cyclohexane-1,2-dicarboxylato κ2O,O′)cobalt(II) monohydrate]
  20. The crystal structure of 3,5,7-trinitro-1,3,5,7-oxatriazocane
  21. Crystal structure of poly[(μ2-nitrato-κ3 O,O′:O′′)(μ2-1-[(2-propyl-1H-benzimidazole-1-yl)methyl]-1H-benzotriazole-k2 N:N′)silver(I)], C17H17AgN6O3
  22. The crystal structure of (5-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-sulfanylidene-1,3,4-oxadiazol-3(2H)-yl)(3-methylphenyl)methanone, C18H14N2O4S
  23. The crystal structure of diaqua-bis[5-(4-methylphenyl)-1H-pyrazole-3-carboxylato-κ2N,O]-cobalt(II), C11H11Co0.5N2O3
  24. Crystal structure of 2-(6-methoxynaphthalen-2-yl)-N-(4-morpholinophenyl)propanamide, C24H26N2O3
  25. The crystal structure of sodium methylsulfonate
  26. Crystal structure of catena-poly[bis(isothiocyanate κ 1 N)-(μ 2-3,3ʹ-methylenebis(1-methyl-1,3-dihydro-2H-imidazole-2-thione)-κ 2 S:S′)-cobalt(II)], C11H12CoN6S4
  27. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1N)nickel(II)} (μ 2-oxo)-hexaoxido-di-molybdenum(VI)─1-methyl-1H-imidazole (1/2), C32H48NiMo2N16O7
  28. 6-(Diphenylphosphoryl)-3,3′,6′-tris(10H-phenoxazin-10-yl)-[1,1′-biphenyl]-2,2′-dicarbonitrile, C62H38N5O4P
  29. The crystal structure of R-2′-amino-N-methyl-N-(1-phenylethyl)-[1,1′-biphenyl]-4-carboxamide, C22H22N2O
  30. The crystal structure of bis{tetrakis(n-butyl)(μ-hydroxy)(2,3,5,6-tetrafluorobenzoate) (μ 3 -oxo)ditin(IV)}
  31. Crystal structure of catena-poly[aqua-(μ 2(3,4-dimethylthieno[2,3-b]thiophene-2,5-dicarboxylato-κ 2 O:O′)-(3,6-bis(4′-pyridyl)-1,2,4,5-tetrazine-κ 1 N)zinc(II)], C22H16N6O5S2Zn
  32. The crystal structure of 3-bromo-5-cyano–N-(5-(cyanomethyl)quinolin-8-yl)pentanamide, C19H15BrN4O
  33. The crystal structure of bis(tetramethylammonium) (di-μ2-aqua)hexaaqua-dibarium(II)) decavanadate
  34. The crystal structure of catena-poly(bis(μ 2-chlorido)- (μ 2-4′-(pyridin-4-yl)-2,2′:6′,2″-terpyridine–N′, N″, N‴:N″″) -chlorido-dicopper(I,II)) monohydrate, C20H16N4OCl3Cu2
  35. Crystal structure of spiropachysine, C31H46N2O
  36. Crystal structure of poly[aqua-(μ 2-3-bromoisonicotinato-κ 2 N: O)-(μ 2-3-bromoisonicotinato-κ 3 N: O: O′)-(μ 3-3-bromoisonicotinato-κ 3 N: O: O′)-(μ 2-nitrite-κ 3 O: O′: O″)dicadmium(II) monohydrate], C19H12Br3Cd2N3O9
  37. The crystal structure of 2-acetylpyridine-ortho-fluoro-phenylhydrazone, C14H12FN3O
  38. The crystal structure of poly(triaqua-(m 2-2,2′-bipyridine-4,4′-dicarboxylato-K 2 O:O′)-bis(m 2-2-2′-bipyridine-4,4′-dicarboxylato-K 4 O,O′:O″:O‴)dierbium(III)) hydrate, C36H26Er2N6O16
  39. The crystal structure of 1,1′-(phenazine-5,10-diyl)bis(heptan-1-one), C26H34N2O2
  40. The crystal structure of (4-([2,2′:6′,2″-terpyridin]-4′-yl)phenyl)boronic acid, C21H16BN3O2
  41. Crystal structure of 6-hydroxy-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione, C6H3N3O3
  42. Crystal structure of N′-((1-hydroxycyclohexyl)(phenyl)methyl)-2-methoxybenzohydrazide ethanol solvate, C23H30N2O4
  43. Crystal structure of pyridinium tetrakis[1,1,1-trifluoro-2,4-pentadionato-K2 O,O′]lutetium(III) C20F12H16LuO8C5H6N
  44. Crystal structure of dichlorido–tetrakis{3-((1H-1,2,4-triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol-k 1N}cobalt(II), C64H88O4N12Cl6Co
  45. The crystal structure of tetrakis(4-allyl-2-methoxyphenyl nicotinato-k 1 N)bis(thiocyanato-k 1 N)cobalt(II)
  46. The crystal structure of methyl 4-(3,4-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C20H21Cl2NO3
  47. The crystal structure of (E)–N-(4-chlorobenzylidene)(4-chlorophenyl)methanamine, C14H11Cl2N
  48. Crystal structure of (E)-4-(4-ethylbenzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C21H22O4
  49. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid dimethyl sulfoxide monosolvate, C4H2N3O4⋅C2H6OS
  50. Crystal structure of-(1S,4aR,5S)-5,6,7-trihydroxy-8-isopropyl-1-methyl-1,2,3,4,5,10,11,11a-octahydro-4a,1-(epoxymethano)dibenzo[a,d][7]annulen-13-one C20H26O5
  51. Crystal structure of 7,9-dimethoxy-2-methyl-4-propylbenzo[f]isoquinolin-5-yl 4-bromobenzoate, C26H24BrNO4
  52. Crystal structure of bis(N,N,N-trimethylbutanaminium)tridecathiotrimolybdate(2−), (BuMe3N)2[Mo3S13]
  53. Crystal structure of N-(adamantan-1-yl)-4-methylpiperazine-1-carbothioamide, C16H27N3S
  54. Crystal structure of poly[(μ 2-2,2′-[1,4-phenylenebis(methylenesulfanediyl)]dibenzoato-κ 4 O,O′:O″,O‴)-(μ 2-1,1′-([1,1′-biphenyl]-4,4′-diyl)bis(1H-benzimidazole)-κ 2 N:N′)cadmium(II)]dimethylformamide solvate, C51H41N5O5S2Cd
  55. The crystal structure of 2-benzoyl-3′,4′,5′,6′-tetrahydrospiro[isoindoline-1,2′-pyran]-3-one, C19H17NO3
  56. The crystal structure of 1-(4-cyanobenzyl)-4-phenyl-1,4-dihydropyridine-3-carbonitrile, C20H15N3
  57. Crystal structure of (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide, C22H22BrO2P
  58. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] tetrachloridomanganese(II)
  59. The crystal structure of 2-(2-hydroxy-4-n-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, C33H39N3O2
  60. Crystal structure of catena-poly[aqua-(5-carboxypyridine-2-carboxylate-κ 2N,O)(2,5-pyridine-dicarboxylate-κ 4O,O′:N:O″)bismuth(III)], C14H9BiN2O9
  61. Crystal structure of (E)-1-fluoro-4-(2-(phenylsulfonyl)vinyl)benzene, C14H11FO2S
  62. Crystal structure of methyl 2-amino-3-chloro-4-methoxybenzoate, C9H10ClNO3
Downloaded on 3.1.2026 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2025-0139/html?lang=en&srsltid=AfmBOorJ3KQzNljoqh3ZfmDL_NpBgDqUb4C-FQpzHq8qyB3PtomJTK7M
Scroll to top button