Organotin Precursors Research Articles

Arylboronic Acid Pinacol Esters as Stable Boron Sources for Dihydrodibenzoborepin Derivatives and a Dibenzoborole.

The general synthesis of boron-containing cyclic compounds (boracycles) necessitates toxic organotin precursors or highly reactive boron halides. Here, we report the synthesis of seven- and five-membered boracycles utilizing arylboronic acid pinacol esters (ArBpins) as stable boron sources. Grignard reagents generated from 2,2'-dibromodibenzyl or 2,2'-dibromobiphenyl reacted with ArBpins, where Ar = 9-anthryl (Anth), 2,4,6-trimethylphenyl (Mes), or 2,4,6-triisopropylphenyl (Tip), to give 10,11-dihydro-5H-dibenzo[b,f]borepins or dibenzoborole derivatives. This Bpin-based method was successfully applied to a one-shot double boracycle formation, providing a dihydrodibenzoborepin-anthracene-dihydrodibenzoborepin triad molecule in a good yield. The dihydrodibenzoborepin bearing the Anth group was directly converted to the unsaturated borepin by NBS/AIBN. All products were characterized by NMR, HRMS, and in some cases, single-crystal X-ray diffraction analysis. Additionally, the photophysical properties of the products are also reported.

Anticancer effect of organotin complexes derived from 2,6-naphthalenedicarboxylic acid by enhancing the ROS generation

Enhancing ROS generation is crucial for anti-metastasis and anti-proliferation effects in anticancer chemotherapeutics. Herein, five organotin complexes [(Ph3Sn)2L] (1) [(R3Sn)2L]n (R = Et 2, R = n-Bu 3), [(n-Bu3Sn)2L(4,4′-bpe)]n (4), [(n-Bu3Sn)2L(4,4′-bipy)]n (5) were synthesized based on appropriate organotin precursors, 2,6-naphthalenedicarboxylic acid (H2L) and auxiliary ligand (4,4′-bipy = 4,4′-bipyridine, 4,4′-bpe = 1,2-di(4-pyridyl)ethylene). It was found that complex 1 exhibits a tetra-coordinated monomeric structure, complexes 2 and 3 show the 2D coordination polymer, and complexes 4 and 5 display the 1D chain with the central tin atoms as all penta-coordinated. These complexes showed high anti-tumor activity in vitro against four cancer cells (A549, HCT116, HepG-2 and HeLa), with IC50 values changed from 0.34±0.01 μM to 25.54 ± 1.55 μM. Additionally, complex 1 could be effective in inhibiting HepG-2 cell migration. Simultaneously, anticancer mechanism studies show that complex 1 induces excessive ROS production in HepG-2 cells, which in turn leads to the occurrence of ROS-induced downstream events, followed by the disintegration of the redox balance, depolarization of mitochondrial membrane potential, nucleus damage and ultimately apoptosis. This work suggests that enhancing the ability of organotin complexes to generate reactive oxygen species and disrupt intracellular redox balance may be a promising anticancer strategy.

Superhydrophobic Pseudosupertetrahedral Sulfido Metalate Clusters for Constructing Liquid Marbles.

One pseudopentasupertetrahedral chalcogenidometalate cluster, [(BuSn)3SnCd4S13(OH)]·6(H+DMP) (PPS-1; H+DMP = protonated 3,5-dimethylpiperidine), has been isolated by use of an organotin precursor. They are arranged to generate two types of tetrahedrally patterned cages, which further interconnect to form a diamond network. Owing to the covalent attachment of abundant alkyl groups, PPS-1 exhibits excellent hydrophobicity and could be used as an assembly substance for building liquid marbles.

Novel Radioiodinated and Radiofluorinated Analogues of FT-2102 for SPECT or PET Imaging of mIDH1 Mutant Tumours.

Isocitrate dehydrogenases (IDHs) are metabolic enzymes commonly mutated in human cancers (glioma, acute myeloid leukaemia, chondrosarcoma, and intrahepatic cholangiocarcinoma). These mutated variants of IDH (mIDH) acquire a neomorphic activity, namely, conversion of α-ketoglutarate to the oncometabolite D-2-hydroxyglutarate involved in tumourigenesis. Thus, mIDHs have emerged as highly promising therapeutic targets, and several mIDH specific inhibitors have been developed. However, the evaluation of mIDH status, currently performed by biopsy, is essential for patient stratification and thus treatment and follow-up. We report herein the development of new radioiodinated and radiofluorinated analogues of olutasidenib (FT-2102) as tools for noninvasive single photon emission computed tomography (SPECT) or positron emission tomography (PET) imaging of mIDH1 up- and dysregulation in tumours. Nonradiolabelled derivatives 2 and 3 halogenated at position 6 of the quinolinone scaffold were synthesised and tested in vitro for their inhibitory potencies and selectivities in comparison with the lead compound FT-2102. Using a common organotin precursor, (S)-[125I]2 and (S)-[18F]3 were efficiently synthesised by radio-iododemetallation and copper-mediated radiofluorination, respectively. Both radiotracers were stable at room temperature in saline or DPBS solution and at 37 °C in mouse serum, allowing future planning of their in vitro and in vivo evaluations in glioma and chondrosarcoma models.

A Convenient Route to New (Radio)Fluorinated and (Radio)Iodinated Cyclic Tyrosine Analogs.

The use of radiolabeled non-natural amino acids can provide high contrast SPECT/PET metabolic imaging of solid tumors. Among them, radiohalogenated tyrosine analogs (i.e., [123I]IMT, [18F]FET, [18F]FDOPA, [123I]8-iodo-L-TIC(OH), etc.) are of particular interest. While radioiodinated derivatives, such as [123I]IMT, are easily available via electrophilic aromatic substitutions, the production of radiofluorinated aryl tyrosine analogs was a long-standing challenge for radiochemists before the development of innovative radiofluorination processes using arylboronate, arylstannane or iodoniums salts as precursors. Surprisingly, despite these methodological advances, no radiofluorinated analogs have been reported for [123I]8-iodo-L-TIC(OH), a very promising radiotracer for SPECT imaging of prostatic tumors. This work describes a convenient synthetic pathway to obtain new radioiodinated and radiofluorinated derivatives of TIC(OH), as well as their non-radiolabeled counterparts. Using organotin compounds as key intermediates, [125I]5-iodo-L-TIC(OH), [125I]6-iodo-L-TIC(OH) and [125I]8-iodo-L-TIC(OH) were efficiently prepared with good radiochemical yield (RCY, 51–78%), high radiochemical purity (RCP, >98%), molar activity (Am, >1.5–2.9 GBq/µmol) and enantiomeric excess (e.e. >99%). The corresponding [18F]fluoro-L-TIC(OH) derivatives were also successfully obtained by radiofluorination of the organotin precursors in the presence of tetrakis(pyridine)copper(II) triflate and nucleophilic [18F]F− with 19–28% RCY d.c., high RCP (>98.9%), Am (20–107 GBq/µmol) and e.e. (>99%).

Assembly of Di-, Tetra- and Hexanuclear Organostannoxanes Using Hemi Labile Intramolecular N→Sn Coordination: Synthesis, Structure, DFT and Antibacterial Studies

Di-, Tetra- and Hexanuclear Organostanoxanes were obtained from the organotin precursors such as (RSnCl3; R = 2-phenylazophenyl) and diorganotin precursor (R2SnCl2; R = 2-phenylazophenyl) having intramolecular N → Sn coordination. RSnCl3 on complete hydrolysis followed by reaction with benzoic acid in different stoichiometry in refluxing dry toluene afforded a hexanuclear [RSn(μ2-O)(μ2-O2CPh]6∙4PhCH3(1) and a dinuclear [(RSn)2(μ2-O)(μ2-O2CPh)2(κ2-O2CPh)2]∙PhCH3(2) monoorganostannoxane clusters. While diorganotin precursor (R2SnCl2; R = 2-phenylazophenyl) on complete hydrolysis in the presence of NaOH afforded a tetranuclear diorganostannoxane macrocycle [R2Sn(µ2-O)]4(3). Single crystal x-ray diffraction analyses revealed that all the three complexes consist Sn centers in different coordination environment acquiring distorted octahedral, distorted pentagonal bipyramidal and distorted trigonal bipyramidal geometry respectively. Complexes 1–3 are further studied for their antibacterial activity which revealed complex 3 shows better antibacterial activity compared to the other complexes. From the DFT studies, we have found that the order of biological activity and HOMO-LUMO gap for these complexes are in similar order (3 > 1 > 2) which suggests that the biological activity and HOMO-LUMO gap are well correlated with each other for these complexes.

Imparting Superhydrophobicity to Porphyrinic Coordination Frameworks Using Organotin

Imparting Superhydrophobicity to Porphyrinic Coordination Frameworks Using Organotin

Organotin(IV) complexes derived from 1,4-naphthalenedicarboxylic acid: synthesis, structure, in vitro cytostatic activity

Seven organotin(IV) complexes, [(R3Sn)2L]n (R = Me 1, R = n-Bu 2), [(Ph3Sn)2L] (3), [(R2Sn)2L(μ3-O)]n (R = Me 4, R = n-Bu 5), [R2SnL(1,10-phen)]n (R = Me 6), [(R2SnCl)2L(1,10-phen)2] (R = n-Bu 7) derived from 1,4-naphthalenedicarboxylic acid (H2L) have been synthesized and characterized by elemental analysis, FT-IR, PXRD, NMR and X-ray crystallography. The single crystal diffraction reveals that complexes 1 and 2 represent 2D network structures, which both contain tetranuclear 26-membered macrocycles. Complexes 3 and 7 display dinuclear tin monomers, which can form 1D infinite chain by C-H···O and C-H···π interactions. Meanwhile, complexes 4 and 5 display 2D network containing tetraorganodistannoxane unit, while complex 6 adopts a 1D infinite chain structure, which further constructs 2D supramolecular architecture through C-H···O intermolecular interactions. What's more, in vitro cytostatic activity of the complexes 1-3 against cervical carcinoma cell lines (HeLa), hepatocellular carcinoma cell lines (HepG-2) and human normal breast cell lines (HBL-100) have been investigated, and the results show that organotin derivatives with n-butyl and phenyl group (2 and 3) exhibit significantly higher anticancer activity than complex 1 with methyl group. Meanwhile, organotin(IV) complexes (1-3) display lower cytotoxicity than corresponding organotin(IV) precursors [trimethyltin chloride, bis(tri-n-butyltin) oxide and triphenyltin chloride] in HBL-100 cells. Furthermore, cytostatic assessments of complex 3 against HepG-2 cells reveal that the effect of cytostatic and apoptotic may through ROS-mediated pathway.

Rational Preparation of Atomically Precise Non-Alkyl Tin-Oxo Clusters with Theoretical to Experimental Insights into Electrocatalytic CO 2 Reduction Applications

Tin oxides (SnO2) have been widely utilized in electronics, nanolithography, and catalysis. As the atomically precise models of SnO2, tin-oxo clusters (TOCs) not only provide opportunities for mech...

Luminescent Pyrene-Decorated Organotin Compounds: Observation of Monomer and Excimer Emission

The pyrene-decorated luminescent organotin compounds Ph3SnO2CPyr (1), [(Bz2Sn)2(μ3-O)(μ-OH)(O2CPyr)]2·2EtOH (2), and t-Bu2Sn[O2CPyr]2 (3) were synthesized from a one-pot reaction between pyrene-1-carboxylic acid (PyrCO2H) and the appropriate organotin precursors. The molecular and crystal structures of 1–3 were determined by single-crystal X-ray diffraction analyses, which reveal rich supramolecular architectures in their crystal structures. The luminescence properties of these compounds were studied in solution as well as in the solid state. While in the solid state all of the compounds reveal excimer bands, in solution, strong monomer emission is seen. Fluorescence lifetime measurements revealed (365 nm) that the average lifetimes of 1–3 in solution could be estimated as 4.97 ns (1), 4.69 ns (2), and 6.93 ns (3).

Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives

Six organotin (IV) complexes with two ligands derived from 2,3‐butanedione and thiosemicarbazide have been synthesized and fully characterized by several spectroscopic techniques, including 119Sn NMR and single crystal X‐ray diffraction. Reactions of the ligand diacetyl‐2‐(thiosemicarbazone)‐3‐(3‐hydroxy‐2‐naphthohydrazone), L1H2, with SnR2Cl2 (R = Me, Bu, Ph) lead to the obtaining of complexes 1–3 with general formula [SnR2L1] (R = Me 1, R = Bu 2, R = Ph 3), in which the ligand is doubly deprotonated and behaves as a N2SO donor, whereas from the reactions of diacetyl‐2‐thiosemicarbazone, HATs, with the same organotin precursors any complex could be isolated. By contrast, reaction of HATs with SnR3Cl induces the ligand cyclization to form a 1,2,4‐triazine‐3‐thione that binds to the metal as a monoanionic donor in a mono or bidentate manner to form compounds 4–6 with formula [SnR3L2] (R = Me 4, R = Bu 5, R = Ph 6). The antimicrobial activity of the ligands and the six complexes was tested towards bacteria and fungi, including clinical isolated strains. The results show that the ligands are devoid of activity, except HATs that displays activity against Bacillus subtilis. Conversely, the complexes exhibit good antimicrobial properties against Gram positive and negative bacteria, yeasts and moulds. The best results are obtained for complexes [SnBu3L2] 5 and [SnPh3L2] 6, indicating that their more lipophilic nature could play an important role in the ease of microbial cell penetration. In some cases, these complexes display similar or higher activity than that of ampicillin and miconazole, used as antibacterial and antifungal positive controls, respectively. Docking study with DHPS protein (S. aureus) has shown that out of six drugs, the compound 6 has the best binding affinity (−8.5 Kcal/mol).

Reactions of 4-diphenylphosphino benzoic acid with organotin oxides and -oxy-hydroxide

The reactions of p-diphenylphosphinobenzoic acid (LCOOH) with various organotin precursors have been carried out. Accordingly, the reaction of $$[n\hbox {-BuSn(O)}(\hbox {OH}]_{\mathrm{n}}$$ with LCOOH afforded the hexameric compound, $$[n\hbox {-BuSn(O)O}_{2}\hbox {C}$$ – $$\hbox {C}_{6}\hbox {H}_{4}$$ – $$p\hbox {-PPh}_{2}]_{6}$$ (1). On the other hand, the reaction of LCOOH with $$[n\hbox {-Bu}_{2}\hbox {SnO}]_{\mathrm{n}}$$ gave the tetrameric compound $$[\{{n}\hbox {-Bu}_{2}\hbox {SnO}_{2}\hbox {C}$$ – $$\hbox {C}_{6}\hbox {H}_{4}$$ – $$p\hbox {-PPh}_{2}\}_{2}\hbox {O}]_{2}$$ (2). The 1-D coordination polymers $$[\hbox {R}_{3}\hbox {SnO}_{2}\hbox {C}$$ – $$\hbox {C}_{6}\hbox {H}_{4}$$ – $$p\hbox {-}\hbox {P(O)Ph}_{2}]_{\mathrm{n}}$$ , $$[\hbox {R} = n\hbox {-Bu}$$ (3), $$\hbox {R} = \hbox {Ph}$$ (4)] were prepared in the reaction of $$[n\hbox {-Bu}_{3}\hbox {Sn}]_{2}\hbox {O}$$ or $$[\hbox {Ph}_{3}\hbox {Sn}]_{2}\hbox {O}$$ with LCOOH. The compounds 1–4 were structurally characterized by multinuclear NMR spectroscopic and single crystal X-ray diffraction studies. SYNOPSIS The reactions of p-diphenylphosphinobenzoic acid with various organotin precursors have been shown to afford hexameric compound 1, tetrameric compound 2 and 1-D polymeric compounds 3 and 4. The compounds 1–4 were structurally characterized by multinuclear NMR spectroscopic and single crystal X-ray diffraction methods.

The Coordination Chemistry in the Antifungal Effect of Tin(IV)-Bis(Pyrimidin-2-Ylthio)Alkane Derivatives

High productivity of agriculture goods is closely associated with the use of fungicides to reduce losses caused by the fungal plant diseases. However, appearance of resistant population of pathogens to several commercial fungicides is a common phenomenon that requires control. There is, therefore, need for developing novel fungicide compounds that are environmentally safe with low toxicity to wild life and humans. In this study novel organotin(IV) derivatives of bis(pyrimidin-2-ylthio)methane (ptm), bis(pyrimidin-2-ylthio)ethane (pte) and bis(pyrimidin-2-ylthio)hexane (pth) were tested against phytopathogens to evaluate their activity as potential fungicides. The bis(pyrimidin-2-ylthio)alkanes were not active in contrast with the organotin(IV) derivatives. The 5-coordinate triphenyltin(IV) derivatives were the most active compounds in a wide range of concentration. This study shows that the microorganisms were susceptible to the acid character of the organotin(IV) precursors.

Stereoselective Ortho Borylation of Pyridylferrocenes

In an effort to develop new routes to planar chiral Lewis acids and Lewis pairs, the borylation of the pyridylferrocenes (pS)-1-stannyl-2-(3,5-dimethylpyrid-2-yl)ferrocene and (pS)-1-mercurio-2-(3,5-dimethylpyrid-2-yl)ferrocene with PhBCl2 was investigated. In both cases, clean conversion to 2-(chlorophenylboryl)-1-(3,5-dimethylpyrid-2-yl)ferrocene, a novel boron–nitrogen heterocycle, was observed. The structures of the products were confirmed by multinuclear and 2D NOESY NMR, high-resolution MS, and single-crystal X-ray diffraction analysis. While all NMR data proved to be identical, the single-crystal X-ray structures revealed retention of stereochemistry for the mercury precursor but inversion of stereochemistry for the organotin precursor. The opposite chirality of the products was further confirmed by chiral HPLC analyses and optical rotation measurements. These results imply that the reaction of PhBCl2 with 1-mercurio-2-(3,5-dimethylpyrid-2-yl)ferrocene proceeded as expected via an ipso-borodemercuration process, whereas a stereoselective rearrangement occurred in the reaction with 1-stannyl-2-(3,5-dimethylpyrid-2-yl)ferrocene. A mechanism is proposed in which the Lewis basic pyridyl group in the stannylferrocene precursor acts as an ortho-directing group that facilitates highly selective attack of a borenium intermediate at the adjacent C–H position. Subsequent proton migration and elimination of Me3SnCl result in a single isomer of the product with inverted stereochemistry. Reactivity studies were performed with Brønsted and Lewis acids to support the proposed mechanism.

Phase and morphology dependence on the annealing temperature of tin sulfides and oxides prepared by thermal decomposition of organotin precursors

Organotin compounds were thermally decomposed in a nitrogen atmosphere. The obtained residues were characterized by X-ray diffraction and scanning electron microscopy. Rietveld refinements of the experimental diffractograms were performed, which enabled the effect of the annealing temperature on the tin residues (oxides and sulfides), micro strain and particle size to be understood. Two organotin compounds (used as precursors) were synthesized and then thermally treated at different temperatures under a dynamic nitrogen flux. The results showed that tetragonal tin (IV) and tin (II) oxides were formed at 485 °C. As the temperature increased to 650 °C, the tin (II) oxide was converted to tin (IV) oxide and metallic tin through a disproportionation reaction. Rods of orthorhombic tin sulfide were obtained at 238 °C with rod lengths of 150–500 nm and diameters of 40–90 nm.

Polymer-Supported Organotin Reagent for Prosthetic Group Labeling of Biological Macromolecules with Radioiodine

In this study, we investigated the use of poly-mer-bound precursor for generating a radiolabeled prosthetic group to be used for conjugate labeling of biological macromolecules. For the approach, a trialkyltin chloride in which the tin was bound to a hydrophilic PEG-based resin support via one of the alkyl groups was synthesized. This resin was then used to prepare a resin-bound trialkyltin benzoic acid, which in some cases was further derivatized on-resin by converting it to a succinimidyl ester. Exposure of the resin-bound compounds to electrophilic radioiodine (¹²⁵I) in either an aqueous or methanol solvent liberated either free radiolabeled [¹²⁵I]iodobenzoic acid or its succinimidyl ester without co-release of the resin-bound precursors. Radiochemical yield was between 35% and 75%, depending on the solvent system and precursor. As example applications for the released compounds, the amine-reactive N-succinimidyl-[¹²⁵I]iodobenzoate prosthetic group was used for conjugate radiolabeling of a peptide, tomato plant systemin, and two proteins, albumin and IgG antibody. These results demonstrate that resin-bound organotin precursors in which the compound to be labeled is tethered to the support via the tin group to be substituted can be used to produce radioiodine-labeled aromatic prosthetic groups in good specific activity without the need for HPLC purification. This solid-phase approach is potentially adaptable to kit-formulation for performing conjugate radiolabeling of biological macromolecules.

Asymmetric Hydrogenation of 3,4-Hexanedione over PtSn Catalysts

In this work, some results of the liquid-phase racemic and enantioselective hydrogenation of 3,4-hex- anedione are presented. The catalysts employed were platinum-based, supported on SiO2. Monometallic catalysts were modified with organotin precursors either chiral (hexa(-)-menthylditin, Men3Sn-SnMen3) or achiral (tetr- abutyltin, SnBu4), and they were obtained via surface organometallic chemistry on metals techniques. Asym- metric system was selective to 4-hydroxyhexan-3-one, the enantiomeric excess achieved being 17%.

Towards a rational design of enantioselective heterogeneous catalysts: Modeling of chiral organotin precursors

In this work, the modeling of organotin compounds of general formula Men-Sn-R 3 (Men = menthyl, R = alkyl or alkoxyalkyl) is carried out. These compounds can be employed as precursors for obtaining enantioselective heterogeneous catalysts, prepared by means of Surface Organometallic Chemistry on Metals techniques. Both Molecular Mechanics and Molecular Dynamics, as well as Density Functional Theory (DFT), were used to give an insight into the relative stability of the Sn–C bonds of several different organotin compounds. The calculations carried out on the molecules Men-Sn-(iso-Bu) 3 and Men-Sn-((1-OCH 3)-Et) 3 showed that if these molecules are used as precursor compounds to prepare heterogeneous organobimetallic catalysts, the probability of losing the menthyl group in a dissociation process is lower, leading to a better performance of the resulting catalysts, in terms of enantiomeric excess.

Synthesis and Some Reactions of Dibutyltin (S)- and (R)-Camphorsulfonyl Hydrides

The synthesis and physical properties of dibutyltin (S)-camphorsulfonyl hydride (1) and dibutyltin (R)-camphorsulfonyl hydride (2), and diphenyltin (S)-camphorsulfonyl hydride (3) as well as that of their organotin precursors are described. Their reactivity with different amines as triethylamine, morpholine and pyridine has been compared with other mixed hydrides as dibutyltin chloride hydride, dibutyltin acetate hydride and dibutyltin dihydride. It has been studied also the possibility of using of dibutyltin (R)- or (S)-camphorsulfonyl hydrides for the stereoselective reduction of different ketones as acetophenone, menthon, camphor and cyclopropyl-(4-metoxyphenyl)-methanone. The reduction of acetophenone with studied camphorsulfonyl hydrides carried out in benzene at room temperature afforded 1-phenylethanol with relatively low enantioselectivity. Addition of 10 equiv. of MnCl(2)*4H(2)O or ZnCl(2) to the reduction mixture involving dibutyltin (S)-camphorsulfonyl hydride (1) and acetophenone and carried out in methanol and tetrahydrofuran, respectively, resulted in remarkable increase in enantioselectivity. The comparative kinetic studies of reduction of acetophenone by different hydrides proved that dibutyltin camphorsulfonyl hydride is significantly more reactive in comparison with dibutyltin chloro hydride and dibutyltin acetate hydride. Analogous results have been obtained from kinetic studies for different tin hydrides with chosen amines. The outcome of these studies supported by theoretical calculations led to the conclusion that the order of reactivity of the studied hydrides correlates with the rate of their homolytic decomposition at room temperature.

Tin Alkylarsonate Clusters: C−H···X (X = Cl, O, and π) Interaction-Mediated Supramolecular Formation

Reactions of Ph3SnCl or Ph3SnOH with the alkylarsonic acids, RAsO3H2, where R = n-propyl, n-butyl, benzyl, and 4-NO2-benzyl, have led to two types of tin oxo clusters: [Sn3Cl3(μ3-O)(R′O)3]2(RAsO3)4 [R = n-Bu, R′ = Et (1); R = n-Pr, R′ = Et (2); R = Bz, R′ = Et (3); R = n-Pr, R′ = Me (4), and R = 4-NO2−Bz, R′ = Et (5)] and [(PhSn)3(RAsO3)3(μ3-O)(OH)(R′O)2]2Sn [R = n-Pr, R′ = Et (6) and R = 4-NO2-Bz, R′ = Et (7)]. Two types of structural units, [Sn3(μ3-O)(μ2-OR′)3] for compounds 1−5 and [Sn3(μ3-O)(μ2-OR′)2] for compounds 6 and 7, were obtained by subtle changes of the organotin precursors. For the first time, hydrogen-bonding interactions such as C−H···Cl, C−H···O, and C−H···π were investigated in the crystal structures of tin alkylarsonate clusters (2−7). The cumulative effects of these weak interactions result in one-, two-, and three-dimensional suparmolecular architectures of 2−7.