Crystallographic report: Bis[tri(o‐chlorobenzyl)tin(IV)] terephthalate

The centrosymmetric structure of (o‐ClC₆H₄)₃SnO₂CC₆H₄CO₂Sn(C₆H₄Cl‐o)₃ features an unsymmetrically chelating carboxylate group, so that a distorted trigonal bipyramidal cis‐C₃O₂ coordination geometry for tin results. Copyright © 2004 John Wiley & Sons, Ltd.     

Synthesis,structure, and fungicidal activity of triorganotin (4H‐1,2,4‐triazol‐4‐yl)benzoates

A series of triorganotin (4H‐1,2,4‐triazol‐4‐yl)benzoates have been synthesized by the reaction of 4‐(4H‐1,2,4‐triazol‐4‐yl)benzoic acid and 3‐(4H‐1,2,4‐triazol‐4‐yl)benzoic acid with (R₃Sn)₂O (R = Et, n‐Bu and Ph) or R′₃SnOH (R′ = p‐tolyl and cyclohexyl). The molecular structure of tri(p‐tolyl)tin 3‐(4H‐1,2,4‐triazol‐4‐yl)benzoate determined by X‐ray crystallography displays that the tin atom adopts a five‐coordinate distorted trigonal bipyramidal geometry with the carboxyl oxygen atom and the nitrogen atom on 1‐position of triazole ring occupying the apical position. Moreover, this complex forms a polymeric chain by the intermolecular Sn–N interactions. All these complexes show good antifungal activities in vitro against Alternaria solani, Cercospora arachidicola, Gibberella zeae, Physalospora piricola, and Botrytis cinerea. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 20:411–417, 2009; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20566     

Syntheses,characterizations, and crystal structures of tri‐ and diorganotin (IV) derivatives with 2‐mercapto‐5‐methyl‐1,3,4‐thiadiazole

A series of organotin(IV) complexes with 2‐mercapto‐5‐methyl‐1,3,4‐thiadiazole (HL) of the type R₃ Sn(L) (R = Me 1 ; Bu 2 ; Ph 3 ; PhCH₂ 4 ) and R₂Sn(L)₂ (R = CH₃ 5 ; Ph 6 ; PhCH₂ 7 ; Bu 8 ) have been synthesized. All complexes 1–8 were characterized by elemental analysis, IR,¹H, ¹³ C, and ¹¹⁹Sn NMR spectra. Among these, complexes 1 , 3 , 4 , and 7 were also determined by X‐ray crystallography. The tin atoms of complexes 1 , 3 , and 4 are all penta‐coordinated and the geometries at tin atoms of complexes 3 and 4 are distorted trigonal–bipyramidal. Interestingly, complex 1 has formed a 1D polymeric chain through Sn and N intermolecular interactions. The tin atom of complex 7 is hexa‐coordinated and its geometry is distorted octahedral. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:353–364, 2006; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20215     

丙酮酸异烟酰腙四核有机锡配合物的合成、表征及{[nBu2Sn(C9H8N3O3)O]SnBu3n}2的晶体结构

The tetranuclear alkyltin(Ⅳ) compounds {[R2Sn(C9H8N3O3)O]SnR3}2 [R=n-Bu (1), 4-CNC6H4CH2 (2),C6H5CH2 (3), 4-ClC6H4CH2 (4)] were prepared by the reaction of Schiff base ligand pyruvic acid isonicotinyl hydrazone with (R3Sn)2O in the corresponding molar ratio of 1:1. All compounds have been characterized by elemental analysis, IR and ^1H NMR spectra. The crystal structure of compound 1 was determined by X-ray single crystal diffractional analysis. This compound exhibits a dimeric structure containing distannoxane units with two types of the tin atoms. For the first tin atom, it appears to be seven-coordinated with a distorted pentagonal bipyramid geometry, and the other is five-coordinated with a distorted trigonal bipyramidal geometry. The molecules are packed in the unit cell in two-dimensional network structure through an interaction between the N atoms of the pyridine and the tin atoms of an adjacent molecule.     

Synthesis,characterization and in vitro antitumour activity of di‐ and tri‐organotin derivatives of fenbufen

The di‐ and tri‐organotin derivatives of fenbufen (4‐(4‐biphenyl)‐4‐oxobutyric acid), [{(n‐C₄H₉)₂Sn(OCOCH₂CH₂COC₆H₄C₆H₅‐4)}₂O]₂ ( 1 ) and R₃SnOCOCH₂CH₂COC₆H₄C₆H₅‐4 (R?C₆H₅, 2 ; c‐C₆H₁₁, 3 ; C₆H₅C(CH₃)₂CH₂, 4 ), have been prepared and characterized by means of elemental analysis, IR and NMR (¹H, ¹³C and ¹¹⁹Sn) spectroscopies. The crystal structure of 1 , bis[4‐(4‐biphenyl)‐4‐oxobutyrato]tetra‐n‐butyldistannoxane, has been determined and it is a centrosymmetric dimer with two distinct types of carboxylate moieties and tin atoms with distorted trigonal bipyramidal geometries. The in vitro antitumour activity of 1 and 2 against two human tumour cell lines was found to be higher than that for cis‐platin used clinically. Copyright © 2005 John Wiley & Sons, Ltd.     

Synthesis,structural characterization and cytotoxic activity of diorganotin(IV) complexes of N‐(5‐halosalicylidene)‐α‐amino acid

Fourteen new diorganotin(IV) complexes of N‐(5‐halosalicylidene)‐α‐amino acid, R′₂Sn(5‐X‐2‐OC₆H₃CH?NCHRCOO) (where X = Cl, Br; R = H, Me, i‐Pr; R′ = n‐Bu, Ph, Cy), were synthesized by the reactions of diorganotin halides with potassium salt of N‐(5‐halosalicylidene)‐α‐amino acid and characterized by elemental analysis, IR and NMR (¹H, ¹³C and ¹¹⁹Sn) spectra. The crystal structures of Bu₂Sn(5‐Cl‐2‐OC₆H₃CH?NCH(i‐Pr)COO) and Ph₂Sn(5‐Br‐2‐OC₆H₃CH?NCH(i‐Pr)COO) were determined by X‐ray single‐crystal diffraction and showed that the tin atoms are in a distorted trigonal bipyramidal geometry and form five‐ and six‐membered chelate rings with the tridentate ligand. Bioassay results of a few compounds indicated that the compounds have strong cytotoxic activity against three human tumour cell lines, i.e. HeLa, CoLo205 and MCF‐7, and the activity decreased in the order Cy>n‐Bu>Ph for the R′ group bound to tin. Copyright © 2005 John Wiley & Sons, Ltd.     

Synthesis,structure and property of diorganotin N‐[(3‐methoxy‐2‐oxyphenyl)methylene]tyrosinates

Five new diorganotin N‐[(3‐methoxy‐2‐oxyphenyl)methylene] tyrosinates, R₂Sn[2‐O‐3‐MeOC₆H₃CH=NCH (CH₂C₆H₄OH‐4)COO] (R = Me, 1 ; Et, 2 ; Bu, 3 ; Cy, 4 ; Ph, 5 ), have been synthesized and characterized by elemental analysis, IR, NMR (¹H, ¹³C and ¹¹⁹Sn) spectra, and the X‐ray single crystal diffraction. In non‐coordinated solvent, complexes 1 – 5 have penta‐coordinated tin atom. In the solid state, 1 – 3 are centrosymmetric dimmers in which each tin atom is seven‐coordinated in a distorted pentagonal bipyramid, and 4 displays discrete molecular structure with distorted trigonal bipyramidal geometry, and the tin atom of 5 is hexa‐coordinated and possess the distorted octahedral geometry with a coordinational methanol molecule. The intermolecular O‐H???O hydrogen bonds in 1 – 4 link molecules into the different one‐dimensional supramolecular chain with R₂² (30) or R₂² (20) macrocycles, and the molecules of 5 are joined into a two‐dimensional supramolecular network containing R₄⁴ (24) and R₄⁴ (28) two macrocycles. Bioassay results against human tumour cell HeLa indicated that 3 ‐ 5 belonged to the efficient cytostatic agents and the activity decreased in the order 4 > 3 > 5 > 2 > 1. The fluorescence determinations show the complexes may be explored for potential luminescent materials.     

Synthesis and characterization of di‐n‐butyltin(IV) complexes with 4′/2′‐nitrobiphenyl‐2‐carboxylic acids: X‐ray crystal structures of [{(n‐C4H9)2Sn(OCOC12H8NO2−4′)}2O]2 and (n‐C4H9)2Sn{OCOC12H8NO2−4′}2

Reactions of di‐n‐butyltin(IV) oxide with 4′/2′‐nitrobiphenyl‐2‐carboxylic acids in 1 : 1 and 1 : 2 stoichiometry yield complexes [{(n‐C₄H₉)₂Sn(OCOC₁₂H₈NO₂?4′/2′)}₂O]₂ ( 1 and 2 ) and (n‐C₄H₉)₂Sn(OCOC₁₂H₈NO₂?4′/2′)₂ ( 3 and 4 ) respectively. These compounds were characterized by elemental analysis, IR and NMR (¹H, ¹³C and ¹¹⁹Sn) spectroscopy. The IR spectra of these compounds indicate the presence of anisobidentate carboxylate groups and non‐linear C? Sn? C bonds. From the chemical shifts δ (¹¹⁹Sn) and the coupling constants ¹J(¹³C, ¹¹⁹Sn), the coordination number of the tin atom and the geometry of its coordination sphere have been suggested. [{(n‐C₄H₉)₂Sn(OCOC₁₂H₈NO₂?4′)}₂O]₂ ( 1 ) exhibits a dimeric structure containing distannoxane units with two types of tin atom with essentially identical geometry. To a first approximation, the tin atoms appear to be pentacoordinated with distorted trigonal bipyramidal geometry. However, each type of tin atom is further subjected to a sixth weaker interaction and may be described as having a capped trigonal bipyramidal structure. The diffraction study of the complex (n‐C₄H₉)₂Sn(OCOC₁₂H₈NO₂?4′)₂ ( 3 ) shows a six–coordinate tin in a distorted octahedral frame containing bidentate asymmetric chelating carboxylate groups, with the n‐Bu groups trans to each other. The n‐Bu? Sn? n‐Bu angle is 152.8° and the Sn? O distances are 2.108(4) and 2.493(5) Å. The oxygen atom of the nitro group of the ligand does not participate in bonding to the tin atom in 1 and 3 . Crystals of 1 are triclinic with space group P1 and of that of 3 have orthorhombic space group Pnna. Copyright © 2003 John Wiley & Sons, Ltd.     

Tetra­butyl­bis(N‐phthaloyl­glycinato)­distannoxane dimer

The crystal structure of the title compound, [Sn₄(C₄H₉)₈(C₁₀H₆NO₄)₄O₂], contains centrosymmetric dimers. It contains a central Sn₂O₂ core with the O atoms bonded to two di­butyl­bis(N‐phthaloyl­glycinato)­tin units. The Sn atoms of the core are six‐coordinate in a skew trapezoidal bipyramidal geometry, while the exocyclic Sn atoms are essentially five‐coordinate in a distorted trigonal geometry. The Sn—C distances lie in a narrow range of 2.120 (5)–2.138 (4) Å.     

(N‐Maleoylglycinato)trimethyltin(IV)

The Sn atom in the crystal structure of the title compound,catena‐poly­[trimethyl­tin‐μ‐[(2,5‐di­oxo‐2,5‐di­hydro­pyrrol‐1‐yl)­acetato‐O:O′]], [Sn(CH₃)₃(C₆H₄NO₄)], adopts a distorted trigonal bipyramidal coordination geometry with three methyl groups defining the trigonal plane [mean Sn—C 2.117 (11) Å] and the axial positions occupied by O atoms from different carboxylate groups, with significantly different Sn—O bond lengths [2.207 (5) and 2.358 (6) Å]. The structure forms a polymeric chain of complex molecules linked via carboxylate moieties.     

Coordination polymers based on building blocks of dimethyltin(IV) Chloride iso‐thiocyanate and dimethyltin(IV) di‐iso‐thiocyanate with pyrazine‐2‐carboxylate and 4, 4′‐bipyridine

The reaction of 4,4′‐bipy with dimethyltin(IV) chloride iso‐thiocyanate affords the one‐dimensional (1D) coordination polymer, [Me₂Sn(NCS)Cl·(4,4′‐bipy)]_n ( 1 ), whereas reaction of dimethyltin(IV) dichloride with sodium pyrazine‐2‐carboxylate in the presence of potassium iso‐thiocyanate affords the two‐dimensional (2D) coordination polymer, {[Me₂Sn(C₄H₃N₂COO)₂]₂ [Me₂Sn(NCS)₂]}_n ( 2 ). Both coordination polymers were characterized by elemental analysis and infrared spectroscopy in addition to ¹H and ¹³C NMR spectroscopy of the soluble coordination polymer ( 1 ). A single‐crystal structure determination showed that the asymmetric unit in 1 contains Me₂Sn(NCS)Cl and 4,4′‐bipy moieties and a 1D infinite rigid chain structure forms through bridging of the 4,4′‐bipy ligand between tin atoms and the geometry around the tin atom is a distorted octahedral. Coordination polymer 2 contains two distinct tin atom geometrics in which one tin atom is seven coordinate, and the other is six coordinate. The two tin atom environments are best described as a pentagonal bipyramidal in the former and distorted octahedral in the latter where the carboxylate groups bridge the two tin atoms and construct a 2D‐coordination polymer. The ¹¹⁹Sn NMR spectroscopy indicates the octahedral geometry of 1 retains in solution. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:699–706, 2011; View this article online at wileyonlinelibrary.com . DOI 10.1002/.20736     

Coordination behaviour of the 2‐(N,N‐dimethylaminomethyl)phenyl ligand towards the di‐t‐butylchlorotin(IV) moiety

{2‐(N,N‐Dimethylaminomethyl)phenyl}(di‐t‐butyl)tin(IV)chloride, {2‐[(CH₃)₂NCH₂]C₆H₄}Sn(t‐Bu)₂ Cl, has been prepared and characterized using NMR and crystallography. This is the first example of a triorganotin(IV) halide containing the 2‐[(CH₃)₂NCH₂]C₆H₄—group as a C,N‐chelating ligand with a weak intramolecular Sn—N interaction because of the steric hindrance of t‐butyl groups. The interatomic Sn—N distance is elongated to 2.904(14) Å and the central tin atom is distorted trigonal bipyramidal. Copyright © 2004 John Wiley & Sons, Ltd.     

Synthesis and Characterization of Archetypal Ladder-Like Dibutyloxotin Cluster Derived from Sterically Encumbered 4-[(<Emphasis Type="Italic">E</Emphasis>)-2-(4-hydroxy-5-methylphenyl)-1-diazenyl]benzoate

Reaction of Bu₂SnO with 4-[(E)-2-(4-hydroxy-5-methylphenyl)-1-diazenyl]benzoic acid in toluene yielded a tetranuclear tin cluster {[Bu₂Sn(O₂CC₆H₄(N=N(C₆H₃-4-OH-5-CH₃))-p)]₂O}₂·2EtOH (1). The complex 1 was characterized using IR spectroscopy, NMR, elemental analysis and single-crystal X-ray diffraction. The compound is a centrosymmetric tetranuclear bis(dicarboxylatotetrabutyldistannoxane) complex containing a planar Sn₄O₂ core in which two μ ₃-oxo O-atoms connect an Sn₂O₂ ring to two exocyclic Sn-atoms. The four carboxylate ligands display two different modes of coordination: syn–syn O, O′-bridging and mono atomic bridge. In the complex, the geometry around the tin atoms is distorted trigonal bipyramidal with an additional longer Sn···O contact.     

Synthesis,structure and cytotoxic activity of diethyltin N‐[(2‐oxyphenyl)methylene]phenylalaninates

Four new diethyltin N‐[(2‐oxyphenyl)methylene]phenylalaninates, (CH₃CH₂)₂Sn[2‐O‐3‐X‐5‐YC₆H₂CH?NCH(CH₂Ph)COO] (X, Y = H, H, 1 ; H, Br, 2 ; H, OCH₃, 3 ; Br, Br, 4 ), have been synthesized and characterized using elemental analysis and infrared and NMR (¹H, ¹³C and ¹¹⁹Sn) spectra. The crystal structures of 1 , 2 , 3 , 4 have been determined. Compounds 1 and 2 have a 12‐membered macrocyclic structure with a trimeric [Sn₃O₆C₃] core. Each tin atom is six‐coordinated in distorted [SnC₂NO₃] octahedral geometry. Compound 3 is a centrosymmetric weak dimer in which the two tin centers are linked by two asymmetric Sn? O???Sn bridges involving the phenolic oxygen of the ligand and two Sn???O interactions from ether oxygen of the adjacent ligand. The coordination geometry of the tin atom can be described as a distorted pentagonal bipyramid with two ethyl groups in axial positions. Compound 4 is a novel binuclear tin complex, formed by the carboxylate of a ligand asymmetrically bridging two tin atoms, which contains a five‐coordinated tin and a six‐coordinated tin. Bioassay results have shown that the compounds have weak in vitro activity against two human tumor cell lines, A549 and CoLo205. Copyright © 2016 John Wiley & Sons, Ltd.     

Organotin(IV) complexes derived from proteinogenic amino acid: synthesis,structure and evaluation of larvicidal efficacy on Anopheles stephensi mosquito larvae

Five new organotin(IV) complexes of composition [Bz₂SnL¹]_n ( 1 ), [Bz₃SnL¹H⋅H₂O] ( 2 ), [Me₂SnL²⋅H₂O] ( 3 ), [Me₂SnL³] ( 4 ) and [Bz₃SnL³H]_n ( 5 ) (where L¹ = (2S )‐2‐{[(E )‐(4‐hydroxypentan‐2‐ylidene)]amino}‐4‐methylpentanoate, L² = (rac )‐2‐{[(E )‐1‐(2‐hydroxyphenyl)methylidene]amino}‐4‐methylpentanoate and L³ = (2S )‐ or (rac )‐2‐{[(E )‐1‐(2‐hydroxyphenyl)ethylidene]amino}‐4‐methylpentanoate) were synthesized and characterized using ¹H NMR, ¹³C NMR, ¹¹⁹Sn NMR and infrared spectroscopic techniques. The crystal structure of 2 reveals a distorted trigonal‐bipyramidal geometry around the tin atom where the oxygen atoms of the carboxylate ligand and a water ligand occupy the axial positions, while the three benzyl ligands are located at the equatorial positions. On the other hand, the analogous derivative of enantiopure L³H ( 5 ) consists of polymeric chains, in which the ligand‐bridged tin atoms adopt the same trans ‐Bz₃SnO₂ trigonal‐bipyramidal configuration and are now coordinated to a phenolic oxygen atom instead of H₂O. In 2 , the OH hydrogen of the ketoimine substituent has moved to the nearby nitrogen atom while in the salicylidene derivative 5 , the OH is located almost midway between the phenolic oxygen atom and the nitrogen atom of the CN group. For the dibenzyltin derivative 1 , a polymeric chain structure is observed as a result of a long intermolecular Sn⋅⋅⋅O bond involving the exocyclic carbonyl oxygen atom from the tridentate ligand of a neighbouring tin‐complex unit. The tin atom in this complex has distorted octahedral coordination geometry. In contrast, the racemic dimethyltin(IV) complexes 3 and 4 display discrete monomeric structures with a distorted octahedral‐ and trigonal‐bipyramidal geometry, respectively. The structures show that the coordination mode of the Schiff base ligand depends primarily on the number of bulky benzyl ligands (R) at the tin atom, as indeed found in the structures of related complexes where R = phenyl. With three bulky R groups, the tridentate chelating O,N,O coordination mode is preferred, whereas with fewer or less bulky R ligands, only the carboxylate and hydroxy groups are involved, which leads to polymers. Larvicidal efficacies of two of the new tribenzyltin(IV) complexes ( 2 and 5 ) were assessed on the second larval instar of Anopheles stephensi mosquito larvae and compared with two triphenyltin(IV) analogues, [Ph₃SnL¹H]_n and [Ph₃SnL³H]_n . The results demonstrate that the compounds containing Sn–Ph ligands are more effective than those with Sn–Bz ligands. Copyright © 2016 John Wiley & Sons, Ltd.     

Crystallographic report: Polymeric [3‐(triphenylgermyl)‐3‐o‐methoxyphenylpropionato]trimethyltin(IV)

The polymeric chains of [Sn(CH₃)₃(C₂₈H₂₅O₃Ge)]_n contain trimethyltin moieties bridging two neighboring 3‐(triphenylgermyl)‐3‐o‐methoxypropionate ligands via carboxyl groups. The germanium atom has a distorted tetrahedral geometry and the tin atom has a distorted trigonal‐bipyramidal geometry, the latter with three methyl groups in the equatorial plane and oxygen atoms defining the axial positions. Copyright © 2005 John Wiley & Sons, Ltd.     

Synthesis,structural characterization and cytotoxic activity of diorganotin(IV) complexes of N‐(5‐halosalicylidene)tryptophane

Four new diorganotin(IV) complexes of N‐(5‐halosalicylidene)tryptophane, R₂Sn[5‐X‐2‐OC₆H₃CH?NCH(CH₂Ind)COO] [Ind = 3‐indolyl; R, X = Et, Cl ( 1 ); Et, Br( 2 ); n‐Bu, Cl ( 3 ); n‐Bu, Br ( 4 )], were synthesized and characterized by elemental analysis, IR and NMR (¹H, ¹³C and ¹¹⁹Sn) spectra. The crystal structures of complexes 1 – 3 were determined by X‐ray single crystal diffraction and showed that the tin atoms are in a distorted trigonal bipyramidal geometry and form five‐ and six‐membered chelate rings with the tridentate ligand. Intermolecular weak interactions in 1–3 link molecules, respectively, into a two‐dimensional array, a one‐dimensional infinite chain and a one‐dimensional double‐chain supramolecular structure. Bioassay results of the compounds indicated that the dibutyltin complexes 3 and 4 have potent in vitro cytotoxic activity against two human tumor cell lines, CoLo205 and Bcap37, while the diethyltin complexes 1 and 2 display weak cytotoxic activity. Copyright © 2008 John Wiley & Sons, Ltd.     

Synthesis,characterization and cytotoxic activity of 5,10,15,20‐tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins

5,10,15,20‐Tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins, (R₃SnO)₄TPP [2, R = Cy (a), Ph (b), PhC(CH₃)₂CH₂ (c)], have been synthesized by the condensation of 4‐(triorganostannyloxy)benzaldehyde, 4‐(R₃SnO)C₆H₄CHO (1), with pyrrole in the presence of BF₃ followed by oxidation by p‐chloranil and characterized by means of elemental analysis, IR, UV–visible and NMR (¹H, ¹³C and ¹¹⁹Sn) spectra. The results of X‐ray single‐crystal diffraction show that 1a and 1b possess a trans‐C₃SnO₂ trigonal bipyramidal geometry with the axial positions occupied by the phenolate oxygen and formyl group oxygen of an adjacent molecule and form a one‐dimensional zigzag chain. In 2a, the macrocyclic core of the porphyrin is coplanar and each tin atom possesses a distorted tetrahedral geometry. These compounds (1 and 2) have potent in vitro cytotoxic activity against two human tumor cell lines – CoLo205 and MCF‐7 – and the activity decreases in the order Ph > Cy > PhC(CH₃)₂CH₂ for the R group bound to tin. Copyright © 2013 John Wiley & Sons, Ltd.     

New Supramolecular Triorganotin(IV) Dithiocarboxylates as Potential Antibacterial Agents

Four triorganotin derivatives of general formula C₁₀H₁₀NS₂SnR₃,_, where R = CH₃ ( 1 ), C₄H₉ ( 2 ), C₆H₁₁ ( 3 ), and C₆H₅ ( 4 ), have been synthesized by the metathesis reaction of 1,2,3,4‐tetrahydroisoquinolnium salt of ligand with triorganotin(IV) chloride in the 1:1 ratio. These complexes were characterized by elemental analysis, Raman, IR, multinuclear NMR (¹H, ¹³C, and ¹¹⁹Sn), and mass spectrometry. The crystal structure confirmed a supramolecular zig‐zag chain structure mediated by S–H (2.968 Å) for complex 4 with the central Sn atom exists in a distorted trigonal bipyramidal geometry. A subsequent antibacterial study indicates that the compounds are biologically active.     

Synthesis,structural characterization and cytotoxic activity of triorganotin 5‐(salicylideneamino)salicylates

Six new triorganotin complexes ( 1a – 1c and 2a – 2c ) of 5‐(salicylideneamino)salicylic acid, [5‐(3‐X‐2‐HOC₆H₃CH═N)‐2‐HOC₆H₃COO]SnR₃ (X = H, 1 ; CH₃O, 2 ; R = Ph, a ; Cy, b ; CH₂C(CH₃)₂Ph, c ), have been synthesized by one‐pot reaction of 5‐aminosalicylic acid, salicylaldehyde and triorganotin hydroxide and characterized using elemental analysis and infrared and NMR (¹H, ¹³C and ¹¹⁹Sn) spectra. The crystal structures of 1a , 1b , 2a ·CH₃OH, 2b ·CH₃OH and 2c ·CHCl₃ have been determined using single‐crystal X‐ray diffraction. In non‐coordinated solvent CDCl₃, the tin atoms in the complexes are all four‐coordinated. In the crystalline state, these compounds adopt a four‐ or five‐coordination mode. Complex 1a exhibits a 44‐membered macrocyclic tetrameric structure with trigonal bipyramidal geometry around the tin atoms in which the axial positions are occupied by the oxygen atom of carboxylate group of the ligand and the phenolic oxygen atom from the adjacent ligand. The coordination geometry of tin atom in 1b and 2c ·CHCl₃ is a distorted tetrahedron shaped by three carbon atoms of alkyl groups and a carboxylate oxygen atom of the ligand. In 2a ·CH₃OH and 2b ·CH₃OH, the tin atom has a distorted trans‐C₃SnO₂ trigonal bipyramidal geometry formed by three alkyl groups, a monodentate carboxylate group and a coordinated methanol molecule. The molecules of 2a ·CH₃OH and 2b ·CH₃OH are linked via O─H···O hydrogen bonds into a one‐dimensional supramolecular chain and a centrosymmetric R₄⁴(22) macrocycle, respectively. Bioassay results against two human tumor cell types (A549 and HeLa) show the complexes are efficient cytostatic agents and may be explored as potential antitumor drugs.