Phenyl Ligands Research Articles

Synthesis and structure of triphenylbismuth bis(phenylcarboranylcarboxylate)

Triphenylbismuth bis(phenylcarboranylcarboxylate) was synthesized by the reaction of triphenylbismuth with phenylcarboranylcarboxylic acid in the presence of hydrogen peroxide. The bismuth atom has a distorted trigonal-bipyramidal coordination with phenyl ligands in equatorial positions. Bond lengths: Bi-C 2.195(3), 2.196(3), 2.204(3) A, Bi-O 2.266(2), 2.276 A. In the molecule there are the donor-acceptor interaction of Bi...O(=C) 2.980(2) and 3.130(3) A. The value of the equatorial angle CBiC from the side of the Bi...O(=C) contact is 141.4(1)°, the angle OBiO is 168.2(1).

C,N-chelated organotin(IV) trifluoroacetates. Instability of the mono- and diorganotin(IV) derivatives.

The C,N-chelated tri-, di- and monoorganotin(IV) halides react with equimolar amounts of CF 3COOAg to give corresponding C,N-chelated organotin(IV) trifluoroacetates. The set of prepared tri-, di- and monoorganotin(IV) trifluoroacetates bearing the L CN ligand (where L CN is 2-( N,N-dimethylaminomethyl)phenyl-) was structurally characterized by X-ray diffraction analyses, multinuclear NMR and IR spectroscopy. In the case of triorganotin(IV) trifluoroacetates and (L CN) 2Sn(OC(O)CF 3) 2, no tendency to form hydrolytic products, or instability towards the moisture was observed. L CNRSn(OC(O)CF 3) 2 (where R is n-Bu or Ph) and L CNSn(OC(O)CF 3) 3 forms upon crystallization from THF in the air mainly dinuclear complexes in which the two tin atoms are interconnected either by hydroxo-bridges or by an oxo-bridge and/or by a bridging trifluoroacetate(s). In the case of hydrolysis of L CN( n-Bu)Sn(OC(O)CF 3) 2, a zwitterionic stannate of formula L CN( n-Bu)Sn(OC(O)CF 3) 2·CF 3COOH was isolated from the mother liquor, too. Products of hydrolysis of L CN( n-Bu)Sn(OC(O)CF 3) 2 and L CNSn(OC(O)CF 3) 3, and some other oxygen bridged organotin(IV) compounds containing the same ligand, were tested as possible catalysts of some transesterification reactions as well as in direct dimethyl carbonate (DMC) synthesis from CO 2 and methanol.

Trimetallic ReBiPt complexes containing spiro-bismuth ligands from the reaction of the bis(tri-t-butylphosphine)platinum with Re 3(CO) 12(μ-BiPh 2)(μ-H) 2

Pt(P-t-Bu 3) 2 reacts with the bismuthtrirhenium complex Re 3(CO) 12(μ-BiPh 2)(μ-H) 2, 1 at 68 °C to give eight complexes PtRe 2(CO) 9P( t-Bu 3)(μ-H) 2, 2, PtRe 3(CO) 12P( t-Bu 3)(μ-Ph)(μ-H)(μ 4-Bi), 3, PtRe 3(CO) 13P( t-Bu 3)(μ 4-Bi)(μ-H) 2, 4, PtRe 4(CO) 16P( t-Bu 3)(μ-H) 2(μ 4-Bi)(μ 3-Bi), 5, Pt 2Re 5(CO) 21[P( t-Bu) 3] 2(μ-H) 3(μ 4-Bi) 2, 6, trans-Pt 2Re 5(CO) 22[P( t-Bu) 3] 2(μ-H) 3(μ 4-Bi) 2, trans-7 , cis-Pt 2Re 5(CO) 22[P( t-Bu) 3] 2(μ-H) 3(μ 4-Bi) 2, cis-7 , (an isomer of trans-7 ) and Re 3(CO) 13[PtPBu t 3] 2(μ-H) 2(μ 4-Bi), 8, all in low yields. When 4 was treated with Pt(P-t-Bu 3) 2 at 68 °C, compounds 2, trans-7 , cis-7 , and Pt 2Re 4(CO) 18[P( t-Bu) 3] 2(μ-H) 2(μ 4-Bi) 2, 9 were formed. When 8 was treated with CO at 25 °C, compounds 2, trans-7 , 9, and PtRe 3(CO) 9P( t-Bu) 3(μ 3-Bi)(μ 4-Bi 2), 10 were formed. In all of the products both of the phenyl rings from the bridging BiPh 2 ligand of 1 were cleaved from the bismuth atom. Only compound 3 contains a phenyl ligand and that ligand was a bridging ligand across the Pt–Re bond. All of the products, except 10, and the known compound 2, contain spiro, μ 4-Bi ligands. The higher nuclearity complexes 5, 6, trans-7 , cis-7 , and 9 contain two bismuth ligands. Compound 10 contains three bismuth atoms. Two of the bismuth atoms in 10 are part of an octahedrally-shaped Re 3PtBi 2 cluster. The third bismuth atom is a triply-bridging ligand on the triangular Re 3 face of the cluster. When a mixture of 4 and 8 was heated to 68 °C in the presence of CO, the new compound PtRe 4(CO) 17(P- t-Bu 3)(μ-H) 2(μ 4-Bi), 11 was formed. The molecular structures of all of the new complexes were characterized by single-crystal X-ray diffraction analyses.

Two Copper(II) Complexes with Mono-Oxime Chelating Ligands: Synthesis, Crystal Structure, and Substituent Effect

Two new complexes, [Cu(L1)2] (1) and [Cu(L2)2(H2O)]·CH3OH (2), have been synthesized via the complexation of copper(II) acetate monohydrate with two mono-oxime chelating ligands (HL1: 4-[(Methoxyimino)(phenyl)methyl]-5-methyl-2-phenyl-1H- pyrazol-3(2H)-one and HL2: 4-[(Ethoxyimino)(phenyl)methyl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one), respectively. X-ray crystal structure determination of the two complexes show that complex 1 consists of one copper(II) ion, two bidentate (L1)− units, and the copper atom of complex 1 has a square planar geometry distorted tetrahedrally with four-coordination, while complex 2 consists of one copper(II) ion, two bidentate (L2)− units, one coordinated H2O, and one crystallizing methanol molecule, as expected from the analytical data. And the copper atom of complex 2 has a slightly distorted tetragonal pyramid geometry with five-coordination. Complex 2 is a self-assembling infinite chain supramolecular structure formed by intermolecular hydrogen bonds. Meanwhile, the photophysical properties of the resulted complexes have also been discussed.

ChemInform Abstract: Combination of Vinyl, Phenyl and Carbonyl Ligands in Ruthenium(II) Complexes: A Route to Vinyl Ketones.

Conversion of chloride complexes [Ru(CO)2(CHCHR)Cl(PMe2Ph)2](R = CMe3 or Ph) into the corresponding phenyl complexes [Ru(CO)2(CHCHR)Ph(PMe2Ph)2] by low-temperature treatment with LiPh is accompanied by a change in the ligand arrangement around the metal. At 20 °C the products undergo two competing rearrangement processes, one a simple isomerisation back to a ligand arrangement analogous to that in [Ru(CO)2(CHCHR)Cl(PMe2Ph)2] and the other a remarkably facile combination of phenyl, carbonyl and vinyl ligands to yield the ketone complexes [Ru(CO)(η4-PhCOCHCHR)(PMe2Ph)2], from which the ketone may be liberated by treatment with Me3CNC.

Aquachlorido{2-[2-(cyclohexylcarbamothioyl-κS)hydrazinylidene-κN1]propanoato(2−)}phenyltin(IV)

In the title organotin compound, [Sn(C6H5)(C10H15N3O2S)Cl(H2O)], the Sn atom is coordinated by the S, O, and imine N atoms of the dinegative tridentate ligand, a chloride ligand, the ipso-C atom of a phenyl ligand and by a water mol­ecule in a distorted octa­hedral coordination environment. Coordin­ated water mol­ecules link the organotin mol­ecules by forming O—H⋯O hydrogen bonds with both carbonyl and carboxyl­ate O atoms, leading to 12-membered {⋯OCO⋯HOH⋯}2 synthons. This results in the formation of supra­molecular chains along the c axis. The chains pack in the ac plane and stack along the b axis with links between layers afforded by N—H⋯Cl hydrogen bonds.

Tri- and diorganostannates containing 2-( N, N-dimethylaminomethyl)phenyl ligand

The C, N-chelated tri and diorganotin(IV) chlorides react with both protic mineral acids and carboxylic acids. The nitrogen atom of the L CN ligand (where L CN is 2-(dimethylaminomethyl)phenyl) is thus quarternized – protonated and new Sn–X bond (X = Cl, Br, I or the remainder of the starting acid used) is simultaneously formed. The set of zwitterionic tri and diorganostannates containing protonated 2-(dimethylaminomethyl)phenyl-moiety was prepared and structurally characterized by multinuclear NMR spectroscopy and XRD techniques. In all these cases, the intramolecular N–H⋯X bond is present in the molecule. Despite the central tin atom remains five-coordinated (except for the [HL CNH] +[( n-Bu) 2SnCl(NO 3) 2] −) and reveals a distorted trigonal bipyramidal geometry, the 119Sn NMR chemical shift values of these zwitterionic stannates are somewhat shifted to the higher field than corresponding starting C, N-chelated tri and diorganotin(IV) halides. Reactions of C, N-chelated organotin(IV) halides with various Lewis acids are also discussed.

Asymmetric Direct Alkynylation Catalyzed by Chiral Ru−Bis(oxazolinyl)phenyl Complexes

Propargylic alcohols were obtained with excellent enantioselectivities in the asymmetric direct alkynylation of aldehydes using 5 mol % of chiral ruthenium complexes containing the chiral bis(oxazolinyl)phenyl ligand.

Synthesis and spectral studies on NiS4, NiS2PN, NiS2P2 chromophores: Single-crystal X-ray structure of [Ni(dbpdtc)2] (dbpdtc = benzyl(4-(benzylamino)phenyl)dithiocarbamate)

Three complexes of a dithiocarbamate ligand (dbpdtc = benzyl(4-(benzylamino)phenyl)dithiocarbamate), namely [Ni(dbpdtc)2] (1), [Ni(dbpdtc)(NCS)(PPh3)] (2) and [Ni(dbpdtc)(PPh3)2]ClO4 (3) have been prepared. The complexes were characterized by IR, electronic spectroscopy and cyclic voltammetry. A single-crystal X-ray structural analysis was carried out for complex 1 and showed that the nickel is in a distorted square planar environment with a NiS4 chromophore. For the two mixed ligand complexes, the thioureide ν C–N values were shifted to higher wavenumbers compared to [Ni(dbpdtc)2], suggesting increased strength of the thioureide bond due to the presence of the π-accepting phosphine. Electronic spectral studies suggest square planar geometries for the complexes. Cyclic voltammetry showed easier reduction of nickel(II) to nickel(I) in the mixed ligand complexes compared to [Ni(dbpdtc)2].

Ping-Pong at Gold: Proton Jump Between Coordinated Phenyl and η1-Benzene Ligands, A Computational Study

A DFT computational investigation predicts that the Au(III) complex (bpy)Au(C(6)H(5))(2+) reacts with benzene to furnish square planar (bpy)Au(C(6)H(5))(eta(1)-C(6)H(6))(2+). Intramolecular processes that occur within this species have been located, and the energetics of all processes have been quantified. The dynamic processes that have been identified are (1) benzene ring rotation with respect to Au, (2) direct hydrogen transfer from the benzene to the phenyl ligand, (3) hydrogen transfer from the ipso to the ortho positions in the coordinated benzene ligand, and (4) hydrogen transfer from the benzenium ligand formed by the ipso/ortho isomerization to the phenyl ligand. Similarities and differences are seen between the behavior of (bpy)Au(C(6)H(5))(eta(1)-C(6)H(6))(2+) and previously reported isoelectronic Pt(II) complexes. Preliminary experimental results related to this chemistry are reported, and possible consequences for C-H bond activation mediated by gold are discussed.

π-Selective stationary phases: (III) Influence of the propyl phenyl ligand density on the aromatic and methylene selectivity of aromatic compounds in reversed phase liquid chromatography

The retention characteristics of phenyl type stationary phases for reversed phase high performance liquid chromatography are still largely unknown. This paper explores the retention process of these types of stationary phases by examining the retention behaviour of linear PAHs and n-alkylbenzenes on a series of propyl phenyl stationary phases that have changes in their ligand density (1.23, 1.31, 1.97, 2.50 μmol m −2). The aromatic and methylene selectivities increased with increasing ligand density until a point where a plateau was observed, overall the propyl phenyl phases had a higher degree of aromatic selectivity than methylene selectivity indicating that these columns are suitable for separations involving aromatic compounds. Also, retention characteristics relating to the size of the solute molecule were observed to be influenced by the ligand density. It is likely that the changing retention characteristics are caused by the different topologies of the stationary phases at different ligand densities. At high ligand densities, the partition coefficient became constant.

Synthesis of (2-hydroxo-5-chlorophenylaminoisonitrosoacetyl)phenyl ligands and their complexes: Spectral, thermal and solvent-extraction studies

Four different types of new ligands Ar(COC(NOH)R)n (Ar=biphenyl, n = 1 H2L 1 ; Ar=biphenyl, n = 2 H4L 2 ; Ar=diphenylmethane, n = 1 H2L 3 ; Ar=diphenylmethane, n = 2 H4L 4 ; R=2�amino�4�chlo� rophenol in all ligands) have been obtained from 1 equivalent of chloroketooximes Ar(COC(NOH)Cl) n (HL 1 -H2L 4 ) and 1 equivalent of 2�amino�4�chlorophenol (for H2L 1 and H2L 3 ) or 2 equivalent of 2�amino� 4�chlorophenol (for H4L 2 and H4L 4 ). (Mononuclear or binuclear cobalt(II), nickel(II), copper(II) and zinc(II) complexes were synthesized with these ligands.) These compounds have been characterized by ele� mental analyses, AAS, infrared spectra and magnetic susceptibility measurements. The ligands have been further characterized by 1 H NMR. The results suggest that the dinuclear complexes of H 2 L 1 and H 2 L 3 have a metal:ligand ratio of 1:2; the mononuclear complexes of H4L 2 and H4L 4 have a metal:ligand ratio of 1:1 and dinuclear complexes H4L 2 and H4L 4 have a metal:ligand ratio of 2:1. The binding properties of the ligands towards selected transition metal ions (Mn II , Co II , Ni II , Cu II , Zn II , Pb II , Cd II , Hg II ) have been established by extraction experiments. The ligands show strong binding ability towards mercury(II) ion. In addition, the thermal decomposition of some complexes is studied in nitrogen atmosphere.

Characterization of stationary phases for reversed‐phase chromatography

Retention characteristics of seven silica-based chromatographic columns (Bidentate C18, Silica-hydride, Spherisorb ODS-1, Resolve C18, XTerra C18, XBridge Phenyl and Blaze C8 Polydentate) were compared. The columns differ in the character of the support, including silica type B, hydrosilated silica, and hybrid silica gel with incorporated methyl groups, or ethylene bridges; further in the type of chemically bonded stationary phase, including C(18), C(8) and phenyl ligands, endcapped and non-endcapped with single point, bidentate and polydentate multi-point attachment to the adsorbent surface. Special attention was focused on hydrophobic and polar selectivity, silanol activity and anion-exclusion. The columns were compared and classified on the basis of the results of the classical column performance tests, retention of homologous n-alkylbenzenes over a broad composition range of aqueous-organic mobile phases and of naphthalene sulphonic acids in aqueous mobile phases without organic solvents.

Di-μ-chlorido-bis{[4-chloro-2-(dimethylaminomethyl)phenyl-κ2C1,N]palladium(II)}

The title compound, [Pd2(C9H11ClN)2Cl2], consists of two Pd atoms which are bridged by two Cl atoms, forming a centrosymmetric binuclear complex with a square-planar coordination for each of the Pd atoms. The Pd atom is chelated by one N and one C atom from a 4-chloro-2-(dimethyl­amino­meth­yl)phenyl ligand, forming a five-membered ring (N—Pd—C—C—C). In the crystal structure, weak C—H ⋯Cl hydrogen bonds link the mol­ecules in rows.

Pincer‐Type Heck Catalysts and Mechanisms Based on PdIV Intermediates: A Computational Study

Pincer-type palladium complexes are among the most active Heck catalysts. Due to their exceptionally high thermal stability and the fact that they contain Pd(II) centers, controversial Pd(II)/Pd(IV) cycles have been often proposed as potential catalytic mechanisms. However, pincer-type Pd(IV) intermediates have never been experimentally observed, and computational studies to support the proposed Pd(II)/Pd(IV) mechanisms with pincer-type catalysts have never been carried out. In this computational study the feasibility of potential catalytic cycles involving Pd(IV) intermediates was explored. Density functional calculations were performed on experimentally applied aminophosphine-, phosphine-, and phosphite-based pincer-type Heck catalysts with styrene and phenyl bromide as substrates and (E)-stilbene as coupling product. The potential-energy surfaces were calculated in dimethylformamide (DMF) as solvent and demonstrate that Pd(II)/Pd(IV) mechanisms are thermally accessible and thus a true alternative to formation of palladium nanoparticles. Initial reaction steps of the lowest energy path of the catalytic cycle of the Heck reaction include dissociation of the chloride ligands from the neutral pincer complexes [{2,6-C(6)H(3)(XPR(2))(2)}Pd(Cl)] [X=NH, R=piperidinyl (1 a); X=O, R=piperidinyl (1 b); X=O, R=iPr (1 c); X=CH(2), R=iPr (1 d)] to yield cationic, three-coordinate, T-shaped 14e(-) palladium intermediates of type [{2,6-C(6)H(3)(XPR(2))(2)}Pd](+) (2). An alternative reaction path to generate complexes of type 2 (relevant for electron-poor pincer complexes) includes initial coordination of styrene to 1 to yield styrene adducts [{2,6-C(6)H(3)(XPR(2))(2)}Pd(Cl)(CH(2)=CHPh)] (4) and consecutive dissociation of the chloride ligand to yield cationic square-planar styrene complexes [{2,6-C(6)H(3)(XPR(2))(2)}Pd(CH(2)=CHPh)](+) (6) and styrene. Cationic styrene adducts of type 6 were additionally found to be the resting states of the catalytic reaction. However, oxidative addition of phenyl bromide to 2 result in pentacoordinate Pd(IV) complexes of type [{2,6-C(6)H(3)(XPR(2))(2)}Pd(Br)(C(6)H(5))](+) (11), which subsequently coordinate styrene (in trans position relative to the phenyl unit of the pincer cores) to yield hexacoordinate phenyl styrene complexes [{2,6-C(6)H(3)(XPR(2))(2)}Pd(Br)(C(6)H(5))(CH(2)=CHPh)](+) (12). Migration of the phenyl ligand to the olefinic bond gives cationic, pentacoordinate phenylethenyl complexes [{2,6-C(6)H(3)(XPR(2))(2)}Pd(Br)(CHPhCH(2)Ph)](+) (13). Subsequent beta-hydride elimination induces direct HBr liberation to yield cationic, square-planar (E)-stilbene complexes with general formula [{2,6-C(6)H(3)(XPR(2))(2)}Pd(CHPh=CHPh)](+) (14). Subsequent liberation of (E)-stilbene closes the catalytic cycle.

FerriCast: A Macrocyclic Photocage for Fe3+

The non-siderophoric Fe(3+) photocage FerriCast (4,5-dimethoxy-2-nitrophenyl)-[4-(1-oxa-4,10-dithia-7-aza-cyclododec-7-yl)phenyl] methanol (2) has been prepared in high yield using an optimized two-step reaction sequence that utilizes a trimethylsilyl trifluoromethanesulfonate (TMSOTf) assisted electrophilic aromatic substitution as the key synthetic step. Spectrophotometric assessment of Fe(3+) binding to FerriCast revealed a binding stoichiometry and metal ion affinity dependent on the nature of the counterion. Exposure of FerriCast to 350 nm light initiates a photoreaction that converts FerriCast into FerriUnc (4,5-dimethoxy-2-nitrosophenyl)-[4-(1-oxa-4,10-dithia-7-aza-cyclododec-7-yl)phenyl]-methanone), which binds Fe(3+) less strongly owing to resonance delocalization of the anilino lone pair into the benzophenone pi-system. The release of Fe(3+) upon photolysis of FerriCast also was evaluated using a previously reported turn-on fluorescent sensor that utilizes the same macrocyclic ligand (4-(1-oxa-4,10-dithia-7-aza-cyclododec-7-yl)phenyl, AT(2)12C4). In contrast to the original reports on AT(2)12C4-based Fe(3+) sensors, FerriCast does not interact with ferric iron in aqueous solution. Introduction of oxygen containing solvents (MeOH, H(2)O, DMSO, MES, and phosphate buffers) to CH(3)CN solutions of metalated FerriCast lead to rapid decomplexation as measured by UV-visible spectroscopy. Further investigations contradicted the published conclusions on the aqueous coordination chemistry of AT(2)12C4, but also confirmed the unique and unexpected selectivity of the macrocycle for Fe(3+) in nonaqueous solvents. The crystallographic analysis of [Cu(AT(2)12C4)Cl](+) provides a rare example of a bifurcated hydrogen bond, and evidence for redox chemistry with the ligand. Spectrophotometric analysis of the model ligand with redox active metal ions provide evidence for AT(2)12C4(*+), a quasi-stable species the presence of which suggests caution should be taken when evaluating the interaction of aniline-containing systems with redox active metal ions.

Unusual transmetallation-induced formation of a C2-symmetric tetrapallada-macrocycle

We report the formation of a tetrapallada-macrocycle induced by an unusual transmetallation, in which an anionic bidentate chelate ligand is replaced by a phenyl ligand from phenylboronic acid, leaving the chloride ligands intact.

Supramolecular networks of polymethylphosphonic acid groups bonded to aromatic platforms: biphenyldiyl-2,2′-bis(methylphosphonic acid) and benzenetriyl-1,3,5-tris(methylphosphonic acid)

Biphenyldiyl-2,2'-bis(methylphosphonic acid) (BBMP) and benzenetriyl-1,3,5-tris(methylphosphonic acid) (BTMP) as ligands have been synthesized from diphenic acid and trimesic acid, respectively. Cu, Mn and Co complexes of BBMP have been prepared but similar complexes of BTMP did not crystallize. However, a copper compound with added 4,4'-bipyridyl was obtained. This copper complex is dimeric in which the dimers are linked into a supramolecular compound through the bipyridyl groups. Interestingly, the structure was solved in P1 with an unusual correlation between the ligand oxygen bond distances and the copper bond distances to water molecules. The Mn and Co BBMP complexes are isostructural in which the BBMP ligands phenyl groups rotate around each other to bridge the metal atoms forming 1:1 linear chains. There are four water molecules bonded to Co that can be removed reversibly. In the case of the Cu compound, one Cu is square planar bonded to four phosphonate oxygen atoms from two BBMP molecules. The second copper is six coordinate adding two water molecules in the axial positions. The two copper ions alternate forming a one dimensional chain but with ligands bonding the chain on both sides. The four coordinate copper atoms are chelated by two BBMP ligands utilizing one oxygen atom from the two phosphonate groups of each ligand and a second oxygen atom from these groups that bridge across the Cu atoms to bond to the six coordinate copper ion. A detailed synthetic procedure for each of the two ligands is supplied as ESI.

Synthesis and characterization of Cu(II) and Ni(II) complexes of some 4-bromo-N-(di(alkyl/aryl)carbamothioyl) benzamide derivatives

4-Bromo-N-(di-R-carbamothioyl)benzamide (R = methyl, ethyl, n-propyl, n-butyl and phenyl) ligands and their Ni(II) and Cu(II) complexes have been synthesized and characterized by elemental analyses, FT-IR and 1H-NMR spectroscopy. The crystal and molecular structure of bis(4-bromo-N-(di-n-propylcarbamothioyl)benzamido)nickel(II) has been determined from single crystal X-ray diffraction data. It crystallizes in the triclinic, space group P 1, Z = 2 with a = 9.286(2) Å, b = 13.215(3) Å, c = 14.125(3) Å, α = 64.180(5)°, β = 85.483(6)°, γ = 83.067(5)°, V = 1548.3(7) Å3 and D Calcd = 1.594 mg m−3. Loss of the N–H proton resonance and the N–H stretching vibration and the shift of the ν C=O and ν C=S stretching vibrations confirm formation of the metal complexes. These studies have shown that the metal complexes are neutral cis-[ML2].

Chloridobis{2-[(dimethylamino)methyl]phenyl}antimony(III)

In the title compound, [Sb(C9H12N)2Cl], the Sb atom adopts a Ψ-trigonal-bipyramidal geometry. The two 2-[(dimethyl­amino)­methyl]­phenyl ligands are coordinated asymmetrically to the Sb atom. The carbon atoms of one of the ligands are disordered over sets of sites with equal occupancy, resulting in two conformational isomers in the crystal. The Sb—C and Sb—N distances in the ordered ligand are: 2.153 (4) and 3.326 (5) Å, respectively. The corresponding distances in the disordered ligand are: 2.103 (5)/2.188 (5) and 2.454 (3) Å, respectively. The structure displays intra­molecular C—H⋯Cl hydrogen bonding.