Crystal structure of {μ2-1,2-bis­[(4-methyl­phenyl­sulfan­yl]-3-oxoprop-1-ene-1,3-di­yl-1:2κ2C3:C1}dicarbon­yl-1κ2C-[μ2-methyl­enebis(di­phenyl­phos­phane)-1:2κ2P:P′](tri­phenyl­phosphane-2κP)iron­platinum(Fe—Pt), [(OC)2Fe(μ-dppm){μ-C(=O)C(4-MeC6H4SCH2)=CCH2SC6H4Me-4}Pt(PPh3)]

Mohamed, A.S.; Jourdain, I.; Knorr, M.; Brieger, L.; Strohmann, C.

doi:10.1107/S2056989020007859

research communications

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ISSN: 2056-9890

Volume 76| Part 7| July 2020| Pages 1087-1091

https://doi.org/10.1107/S2056989020007859

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Crystal structure of {μ₂-1,2-bis[(4-methylphenylsulfanyl]-3-oxoprop-1-ene-1,3-diyl-1:2κ²C³:C¹}dicarbonyl-1κ²C-[μ₂-methylenebis(diphenylphosphane)-1:2κ²P:P′](triphenylphosphane-2κP)ironplatinum(Fe—Pt), [(OC)₂Fe(μ-dppm){μ-C(=O)C(4-MeC₆H₄SCH₂)=CCH₂SC₆H₄Me-4}Pt(PPh₃)]

Ahmed Said Mohamed,^a,^b Isabelle Jourdain,^b Michael Knorr,^b Lukas Brieger ^c and Carsten Strohmann ^c ^*

^aCentre D'Etude et de Recherche de Djibouti, Djibouti, ^bInstitut UTINAM UMR 6213 CNRS, Université Bourgogne Franche-Comté, 16 Route de Gray, 25030 Besançon, France, and ^cInstitute for Inorganic Chemistry, Faculty of Chemistry and Chemical Biology, TU Dortmund University, Otto-Hahn Str. 6, 44227 Dortmund, Germany
^*Correspondence e-mail: carsten.strohmann@tu-dortmund.de

Edited by S. Parkin, University of Kentucky, USA (Received 15 May 2020; accepted 10 June 2020; online 16 June 2020)

The title compound, [FePt(C₁₉H₁₈OS₂)(C₁₈H₁₅P)(C₂₅H₂₂P₂)(CO)₂], 1, [(OC)₂Fe(μ-dppm)(μ-C(=O)C(CH₂SC₆H₄Me-4)=CCH₂SC₆H₄Me-4)Pt(PPh₃)], represents the first example of a diphosphane-bridged heterobimetallic Fe—Pt dimetallacyclopentenone complex resulting from a bimetallic activation of metal-coordinated carbonyl ligand with an internal alkyne, namely 1,4-bis(p-tolylthio)but-2-yne. The bridging μ₂-C(=O)C(CH₂SC₆H₄Me-4)=CCH₂SC₆H₄Me-4 unit (stemming from a carbon–carbon coupling reaction between CO and the triple bond of the alkyne dithioether) forms a five-membered dimetallacyclopentenone ring, in which the C=C bond is π-coordinated to the Fe center. The latter is connected to the Pt center through a short metal–metal bond of 2.5697 (6) Å.

Keywords: crystal structure; internal alkyne; iron; platinum; heterobimetallic; metal–metal bond; dimetallcyclopentenone; bis(diphenylphosphino)methane; thioether; hydrogen bonding.

CCDC reference: 1996804

1. Chemical context

Acetylenic dithioether ligands of type RSCH₂C≡CCH₂SR (R = aryl, alkyl) have in recent years not only attracted attention as reactive building blocks for further organic transformations (Pourcelot & Cadiot, 1966 ; Everhardus & Brandsma; 1978 ; Levanova et al., 2015 ) but also as promising ligands for coordination chemistry because of their dytopic character, allowing both coordination to soft metal centers through dative M←S bonding and π-bonding via the acetylenic triple bond. In this context, we have explored in a series of several papers the coordination of this ligand family to CuX salts in a self-assembly process to discrete molecular compounds, mono- and bidimensional coordination polymers and three-dimensional MOFs. For example, treatment of CuI with PhSCH₂C≡CCH₂SPh afforded a three-dimensional network incorporating Cu₆(μ₃-I) hexagonal prisms as connection nodes (Knorr et al., 2009 ; Bai et al., 2018 ). In contrast, reaction of BzSCH₂C≡CCH₂SBz (Bz = benzyl) with both CuI and CuBr provided simple isostructural dinuclear zero-dimensional complexes [{Cu(μ₂-X)₂Cu}(μ-BzSCH₂C≡CCH₂SBz)₂] (X = I, Br). A far more original material resulted from coordination to CuCl, yielding a luminescent 2D material [{Cu₂(μ₂-Cl)(μ₃-Cl)}(μ-BzSCH₂C≡CCH₂SBz)]_n, in which the layers are assembled both by dative Cu—S thioether bonds and organometallic Cu-π–acetylenic interactions via the triple bond of the ligand. Furthermore, the Cu^I centers are interconnected through μ₂- and μ₃-bound chloro ligands. Treatment of CuI with the isomeric p-TolSCH₂C≡CCH₂STol-p (Tol = C₆H₄-p-Me) ligand led to the formation of a 2D network [{Cu₄(μ₃-I)₄}(μ-TolSCH₂C≡CCH₂STol)₂]_n with closed cubane-type clusters as SBUs (Secondary Building Units), whilst with CuBr the 1D [{Cu(μ₂-Br)₂Cu}(μ-TolSCH₂C≡CCH₂STol)₂]_n coordination polymer was generated (Aly et al., 2014 ; Bonnot et al., 2015 ). An alternative approach to combining a metallic scaffold with RSCH₂C≡CCH₂SR-type ligands has been developed by Went and coworkers, who post-functionalized dicobaltatetrahedrane complexes [Co₂(μ-HOCH₂C≡CCH₂OH)(CO)₆] in the presence of HBF₄·OEt₂ and various thiols RSH to obtain [Co₂(μ-RSCH₂C≡CCH₂SR)(CO)₆] and [Co₂(μ-RSCH₂C≡CCH₂SR)(μ-dppm)(CO)₄] [dppm = bis(diphenylphosphino)methane], respectively. Similar treatment of [Mo₂(μ-HOCH₂C≡CCH₂OH)(CO)₄Cp₂] with EtSH yielded [Mo₂(μ-EtSCH₂C≡CCH₂SEt)(CO)₄Cp₂]. These former Co–Co thioether complexes were then employed as metalloligands to coordinate further metal fragments such as [Cu(MeCN)₄]PF₆, AgBF₄ and [Mo(CO)₄(norbornadiene)] (Bennett, et al., 1992 ; Gelling et al., 1993 ). Related dicationic salts such as [(Co₂(CO)₆)₂-μ,η²,η²-(Me₂S—CH₂C≡CCH₂SMe₂)][BF₄]₂ have also been described (Amouri et al., 2000 ). We and Shaw's group have demonstrated that upon treatment of the μ-carbonyl complex [(OC)₃Fe(μ-dppm)(μ-CO)Pt(PPh₃)] with ArC≡CH (Ar = Ph, p-Tol, 2,4,5-trimethylphenyl, p-C₆H₄F, 2,4-C₆H₃F₂, p-C₆H₄CF₃), dimetallacyclopentone complexes are formed, stemming from carbon–carbon coupling reactions between CO and the terminal alkyne (Fontaine et al., 1988 ; Jourdain et al., 2013 ; Knorr & Jourdain, 2017 ; Brieger et al., 2019 ). The first step involves the formation of a kinetic isomer [(OC)₂Fe(μ-dppm){μ-C(=O)C(H)=C(Ar)}Pt(PPh₃)], which then evolves to the thermodynamic one [(OC)₂Fe(μ-dppm){μ-C(=O)C(Ar)=C(H)}Pt(PPh₃)]. We were now intrigued as to whether this route may be extended to internal alkynes RC≡CR, which are in general less reactive than terminal ones. We therefore probed the possibility of coupling [(OC)₃Fe(μ-dppm)(μ-CO)Pt(PPh₃)] with p-TolSCH₂C≡CCH₂STol-p in hot toluene as solvent and succeeded in isolating the targeted dimetallacyclopentone [(OC)₂Fe(μ-dppm)(μ-C(=O)C(4-MeC₆H₄SCH₂)=CCH₂SC₆H₄Me-4)Pt(PPh₃)] (1) as a stable crystalline product according to the reaction scheme shown in Fig. 1. With this title compound 1 in hand, we now have the possibility of coordinating other metal fragments in upcoming studies, for example [Mo(CO)₄(norbornadiene)] or ReBr(CO)₅ in a chelating manner using the two adjacent thioether arms or of constructing coordination networks incorporating complex 1 as an organometallic building block by coordination of CuX or Ag^I salts on the S-donor sites (see above).

Figure 1
The reaction scheme for the synthesis of 1.

2. Structural commentary

The heterobimetallic compound 1 crystallizes in the monoclinic crystal system, space group P2₁/c. The molecular structure is depicted in Fig. 2 and selected bond lengths and angles are given in Table 1.

Table 1
Selected geometric parameters (Å, °)

Pt1—Fe1	2.5697 (6)	Fe1—C2	2.119 (4)
Pt1—P2	2.2850 (10)	Fe1—C3	1.932 (5)
Pt1—P3	2.2714 (12)	Fe1—C20	1.777 (5)
Pt1—C1	2.045 (4)	Fe1—C21	1.789 (5)
Fe1—P1	2.1966 (12)	O3—C3	1.216 (5)
Fe1—C1	2.162 (4)	C1—C2	1.407 (6)

P2—Pt1—Fe1	97.26 (3)	C1—Fe1—C2	38.35 (16)
P3—Pt1—Fe1	161.46 (3)	C20—Fe1—P1	95.66 (14)
P3—Pt1—P2	100.53 (4)	C21—Fe1—P1	102.63 (13)
C1—Pt1—Fe1	54.44 (12)	C3—Fe1—P1	88.88 (13)
C1—Pt1—P2	151.36 (12)	C1—Fe1—P1	141.85 (12)
C1—Pt1—P3	107.33 (12)	C2—Fe1—P1	130.91 (13)
Pt1—C1—Fe1	75.25 (13)	C20—Fe1—Pt1	168.78 (14)
C20—Fe1—C3	101.5 (2)	C21—Fe1—Pt1	87.76 (14)
C20—Fe1—C21	96.5 (2)	C2—Fe1—Pt1	73.72 (12)
C21—Fe1—C3	157.6 (2)	C1—Fe1—Pt1	50.30 (11)
C20—Fe1—C1	119.19 (18)	C3—Fe1—Pt1	72.18 (13)
C21—Fe1—C1	89.16 (18)	P1—Fe1—Pt1	93.50 (4)
C3—Fe1—C1	70.43 (18)	C2—C1—Pt1	109.1 (3)
C20—Fe1—C2	95.33 (18)	C2—C1—Fe1	69.2 (2)

Figure 2
The molecular structure of the title complex 1, with atom labeling. Displacement ellipsoids are drawn at the 30% probability level.

The Fe—Pt bond [2.5697 (6) Å] is spanned by a dppm ligand and bridged by the C(=O)C(R)=C(R) (R = 4-MeC₆H₄SCH₂) unit resulting from the carbon–carbon coupling reaction between CO and the alkyne. This value, which is less than 2.6 Å, is in the usual range for FePt(dppm)–dimetallacyclopentenone complexes. Note that extreme Fe—Pt distances are reported for the μ-carbene [(OC)₃Fe{μ-C(Et)OSi(OMe)₃}(μ-dppm)Pt(PPh₃)] [d(Fe—Pt) = 2.5062 (9) Å; YOTCIT; Braunstein et al., 1995 ] and [Fe(η⁵-C₅H₄S)₂Pt(PPh₃)] [d(Fe—Pt = 2.935 (2) Å; FENCUW; Akabori et al., 1987 ]. Coupling of an internal alkyne does not affect the structural features of the [FeC(=O)C(R)=C(R)Pt] motif significantly with respect to carbon–carbon coupling with a terminal alkyne. The relevant bond lengths and angles are very similar to those of other Fe—Pt structures published by Fontaine et al. (1988) and our group (see above). The presence of a bulky substituent on the C1 atom bound to platinum implies a significant reduction of the P3—Pt—P2 angle [100.53 (4)°] concomitant with an increasing value of the angle P3—Pt—C1 of 107.33 (12)°. In related compounds described previously in the literature, these P3—Pt—P2 angles usually lie in the range 103.93 (8) to 106.63 (3)°, as exemplified by [(OC)₂Fe(μ-dppm){μ-C(=O)C{(CH₂)₃CCH}=C(H)}Pt(PPh₃)] (REDNEU) and [(OC)₂Fe(μ-dppm){μ-C(=O)C(p-C₆H₄CF₃)=C(H)}Pt(PPh₃)] (PIXLAL), and 98.8 (3) to 104.95 (10)° for P3—Pt—C1 in [(OC)₂Fe(μ-dppm){μ-C(=O)C(H)=C(H)}Pt(PPh₃)] (FEYBAM) and [(OC)₂Fe(μ-dppm){μ-C(=O)C(o,p-C₆H₃F₂)=C(H)}Pt(PPh₃)] (PIXKUE) (Fontaine et al., 1988; Jourdain et al., 2006 , 2013). The crystal structure of the dithioether p-TolSCH₂C≡CCH₂STol-p (MULHUZ) was reported by Aly et al. (2014). After complexation and a coupling reaction with a CO ligand, the C1—C2 bond is considerably longer [1.407 (6) vs 1.266 (5) Å] as a result of the conversion to an olefinic moiety, σ-bound to Pt and η²-coordinated to Fe. The alkyne bending angles are disparate [C1—C2—C4 = 126.2 (4), C2—C1—C12 = 119.6 (4)°] as well as the C1—C12 and C2—C4 distances [d(C1—C12) = 1.483 (6), d(C2—C4) = 1.511 (5) Å]. Compared to 1,4-bis(p-tolylthio)but-2-yne, the C—S bonds are also considerably elongated [d(C4—S1 = 1.830 (4), d(C12—S2) = 1.808 (4), d(C5—S1) = 1.782 (5), d(C13—S2) = 1.771 (4) vs 1.685 (2) and 1.714 (2) Å] but they fit well with those encountered in the dimetallatetrahedrane [Co₂{μ-C₂(CH₂SMe)₂Mo(CO)₄}(μ-dppm)(CO)₄] [d(C—S = 1.827 (4), 1.833 (4),1.790 (5) and 1.819 (5) Å; JIHMUI10; Gelling et al., 1993].

3. Supramolecular features

In the crystal, the individual molecules are linked by weak intermolecular interactions; for example a contact between O3′′⋯H39 [d = 2.49 Å and C3′′—O3′′⋯H39 = 138°; symmetry code: (′′) −x + 1, −y + 1, −z + 1] occurs (Fig. 3, Table 2. A second, yet still weaker intermolecular interaction of 2.67 Å is observed between the O1′⋯H15 [symmetry code: (′) x, –y + $[{3\over 2}]$ , z − $[{1\over 2}]$ ] atoms of two adjacent molecules. In addition there is an intramolecular contact between O3⋯H34A (d = 2.62 Å and C3—O3⋯H34A = 125°). Furthermore, there are also several loose intermolecular C—H⋯π interactions present; for example a contact between C43—H43 and the midpoint of the C13=C14 double bond [d(H43⋯midpoint) = 2.73 Å and C—H⋯midpoint = 157°] of a tolyl ring attached to S2, as well as between C62—H62 and the C23—C24—C25 atoms of a phenyl ring [d(H62⋯centroid) = 2.64 Å and C—H⋯centroid = 148°] attached at P1. However, since all hydrogen atoms were not refined freely, a more accurate discussion of the bond lengths and angle is not appropriate.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1ⁱ	0.93	2.67	3.316 (6)	128
C34—H34A⋯O3	0.97	2.62	3.271 (5)	125
C39—H39⋯O3ⁱⁱ	0.93	2.49	3.239 (6)	138
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Figure 3
A partial view along the a axis of the crystal packing of the title compound. The hydrogen bonds (Table 2

) are shown as dashed lines.

4. Database survey

Other examples of crystallographically characterized dimetallacyclopentenone complexes are Fe₂Cp₂(CO)(μ-CO){μ-CH=C(Ph)C(=O)} (DAHTAJ; Boni et al., 2011 ), Fe₂Cp*₂(CO)(μ-CO){μ-C(C≡CH)=CHC(=O)] (JUZHIV; Akita et al., 1993 ), Fe₂(CO)₅(μ-dppm){μ-C(=O)CH=CH} (GACWIQ10; Knox et al., 1995 ), Fe₂(CO)₅(μ-dppm){μ-C(=O)C(Ph)=CH} (PIHMOI; Hitchcock et al., 1993 ), Fe₂Cp₂(CO)(μ-CO){μ-C(COR)=C(Me)C(=O)} (R = Ph, Bu) (SIZNUK, SIZPAS; Wong et al., 1991 ), Fe₂{(η-C₅H₄)₂SiMe₂}(CO)₂(μ-CO){μ-C(Ph)=C(H)C(=O)} (ZUZGIK; McKee et al., 1994 ), Ru₂(CO)₄(μ-dppm)₂{μ-C(=O)C(CO₂Me)=C(CO₂Me)} (JITZAN; Johnson & Gladfelter, 1991 ), Ru₂(CO)₄(μ-dppm)₂{μ-CH=CHC(=O)} (LIFYUU; Mirza et al., 1994 ), Ru₂(η-C₅HMe₄)₂(CO)(μ-CO){μ-C(=O)C(R)=C(R)} (R = Et, Me) (NEMVOS, NEMVUY; Horiuchi et al., 2012 ), Rh₂Cp₂(CO)₄{μ-C(CF₃)=C(CF₃)C(=O)} (TFPNRH; Dickson et al., 1981 ), Re₂Cp*₂(CO)₂{μ-CH=C{C(=CH₂)CH₃}C(=O)} (WEZKIV; Casey et al., 1994 ). A rare example of a heterodinuclear combination is CpFe{μ-C(=O)C(CMe₂OH)=CH}(μ-CO)Ru(CO)Cp* (FEHGOP; Dennett et al., 2005 ). We are also aware of OsRu(CO)₈{μ-HC=CHC(=O)} (Kiel et al., 2000 ), but for the latter compound no structural data are available.

5. Synthesis and crystallization

[(OC)₃Fe(μ-CO)(μ-dppm)Pt(PPh₃)] (200 mg, 0.2 mmol) was treated with an excess of 1,4-bis(p-tolylthio)but-2-yne (100 mg, 0.4 mmol) in toluene (5 mL). The solution was stirred at 363 K for 6h. The reaction mixture was filtered, and all volatiles removed under reduced pressure. The brown residue was redissolved in a minimum of toluene. Orange–yellow crystals were isolated by layering with heptane (152 mg, 76% yield).

Calculated for C₆₄H₅₅FeO₃P₃PtS₂ (1279.18 g mol⁻¹): C, 60.05; H, 4.36. Found: C, 59.80; H, 4.21. ¹H NMR: δ 2.21 (s, 3H, CH₃), 2.28 (s, 3H, CH₃), 3.67 (br, 2H, CH₂), 3.97(br, 2H, CH₂), 4.53 (br, 2H, PCH₂P, ²J_PtH = 41), 6.45–7.85 (m, 43H, Ph). ³¹P{1H} NMR: δ 6.8 (d, P_{dppm Pt}, ²J_PP = 57, ^2 + 3J_PP = 5, ¹J_PtP = 2543), 32.7 (d, P_{PPh3 Pt}, ³J_PP = 32, ^2 + 3J_PP = 5, ¹J_PtP = 3506), 63.4 (dd, P_{dppm Fe}, ²J_PP = 57, ³J_PP = 32, ¹J_PtP = 135). IR(toluene): 1966, 1918s ν(CO), 1696m ν(C=O).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All of the hydrogen atoms were placed in geometrically calculated positions and each was assigned a fixed isotropic displacement parameter based on a riding model: C—H = 0.93–0.97 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Table 3
Experimental details

Crystal data
Chemical formula	[FePt(C₁₉H₁₈OS₂)(C₁₈H₁₅P)(C₂₅H₂₂P₂)(CO)₂]
M_r	1280.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.0071 (6), 36.1737 (15), 13.6980 (6)
β (°)	111.970 (5)
V (Å³)	5517.5 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.01
Crystal size (mm)	0.23 × 0.15 × 0.05

Data collection
Diffractometer	Agilent Technologies Xcalibur, Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.837, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	47863, 10566, 8245
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.076, 1.03
No. of reflections	10566
No. of parameters	669
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.12, −0.64
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 1996804

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989020007859/pk2630sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020007859/pk2630Isup3.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

{µ₂-1,2-Bis[(4-methylphenylsulfanyl]-3-oxoprop-1-ene-1,3-diyl-1:2C³:C¹}dicarbonyl-1κ²C-[µ₂-methylenebis(diphenylphosphane)-1:2κ²P:P'](triphenylphosphane-2κP)ironplatinum(Fe—Pt) top

Crystal data top

[FePt(C₁₉H₁₈OS₂)(C₁₈H₁₅P)(C₂₅H₂₂P₂)(CO)₂]	F(000) = 2576
M_r = 1280.05	D_x = 1.541 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.0071 (6) Å	Cell parameters from 9511 reflections
b = 36.1737 (15) Å	θ = 2.7–28.7°
c = 13.6980 (6) Å	µ = 3.01 mm⁻¹
β = 111.970 (5)°	T = 293 K
V = 5517.5 (5) Å³	Plate, yellow
Z = 4	0.23 × 0.15 × 0.05 mm

Data collection top

Agilent Technologies Xcalibur, Sapphire3 diffractometer	10566 independent reflections
Radiation source: Enhance (Mo) X-ray Source	8245 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 16.0560 pixels mm^-1	θ_max = 25.8°, θ_min = 2.2°
ω scans	h = −11→14
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	k = −44→41
T_min = 0.837, T_max = 1.000	l = −16→16
47863 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0274P)² + 0.5475P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.005
10566 reflections	Δρ_max = 1.12 e Å⁻³
669 parameters	Δρ_min = −0.64 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Crystal structure determination of compound 1 was accomplished on an Oxford diffraction Xcalibur S Diffractometer. Suitable crystals of 1 were covered with an inert oil (perfluoropolyalkylether and used for X-ray crystal structure determination. Graphite monochromated Mo-Kα radiation (λ = 0.71073?Å) was used. The processing and finalization of the crystal structure was done with the program Olex2 (Dolomanov, 2009). The crystal structures were solved by intrinsic phasing (SHELXT; Sheldrick, 2015a) and refined against F2 with the full-matrix least-squares method (SHELXL; Sheldrick, 2015b). A multi-scan absorption correction using the CrysAlis RED program (Oxford Diffraction, 2010) was employed. The non-hydrogen atoms were refined anisotropically.

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

	x	y	z	U_iso*/U_eq
Pt1	0.33424 (2)	0.62472 (2)	0.31155 (2)	0.01386 (6)
Fe1	0.52875 (5)	0.66228 (2)	0.35654 (4)	0.01541 (14)
S1	0.51458 (12)	0.61606 (4)	0.02018 (9)	0.0335 (3)
S2	0.19884 (11)	0.69548 (4)	0.12684 (8)	0.0242 (3)
P1	0.60180 (10)	0.64353 (3)	0.52099 (8)	0.0160 (3)
P2	0.36370 (10)	0.60649 (3)	0.47912 (8)	0.0136 (2)
P3	0.16428 (10)	0.59290 (3)	0.21914 (8)	0.0166 (3)
O1	0.3898 (3)	0.72834 (9)	0.3663 (2)	0.0305 (8)
O2	0.7452 (3)	0.70095 (9)	0.3644 (3)	0.0331 (8)
O3	0.6059 (3)	0.58365 (9)	0.3412 (2)	0.0226 (7)
C1	0.3927 (4)	0.64918 (12)	0.2048 (3)	0.0167 (10)
C2	0.5040 (4)	0.63378 (12)	0.2148 (3)	0.0184 (10)
C3	0.5576 (4)	0.61346 (14)	0.3138 (3)	0.0199 (11)
C4	0.5728 (4)	0.64158 (13)	0.1445 (3)	0.0214 (10)
H4A	0.656425	0.635059	0.181663	0.026*
H4B	0.569106	0.667854	0.129478	0.026*
C5	0.5750 (4)	0.57103 (14)	0.0594 (3)	0.0284 (12)
C6	0.5322 (5)	0.54791 (15)	0.1179 (4)	0.0356 (13)
H6	0.469522	0.555719	0.137208	0.043*
C7	0.5815 (5)	0.51369 (15)	0.1475 (4)	0.0413 (15)
H7	0.552057	0.498782	0.187748	0.050*
C8	0.6741 (5)	0.50038 (15)	0.1194 (4)	0.0398 (14)
C9	0.7145 (5)	0.52324 (16)	0.0597 (4)	0.0436 (15)
H9	0.775600	0.514984	0.038988	0.052*
C10	0.6673 (5)	0.55811 (16)	0.0295 (4)	0.0364 (14)
H10	0.696839	0.572966	−0.010742	0.044*
C11	0.7276 (6)	0.46250 (16)	0.1544 (5)	0.065 (2)
H11A	0.743383	0.459346	0.227930	0.097*
H11B	0.801292	0.460237	0.142632	0.097*
H11C	0.672116	0.443892	0.114692	0.097*
C12	0.3296 (4)	0.67416 (13)	0.1153 (3)	0.0208 (11)
H12A	0.305131	0.660195	0.050210	0.025*
H12B	0.384620	0.693322	0.112025	0.025*
C13	0.1237 (4)	0.71380 (13)	−0.0009 (3)	0.0213 (11)
C14	0.1814 (4)	0.72895 (13)	−0.0630 (3)	0.0256 (11)
H14	0.264781	0.728200	−0.039538	0.031*
C15	0.1159 (4)	0.74513 (14)	−0.1592 (3)	0.0299 (12)
H15	0.156559	0.755564	−0.198448	0.036*
C16	−0.0078 (4)	0.74615 (13)	−0.1983 (3)	0.0264 (11)
C17	−0.0649 (4)	0.73051 (14)	−0.1363 (3)	0.0286 (12)
H17	−0.148331	0.730799	−0.160551	0.034*
C18	−0.0010 (4)	0.71470 (13)	−0.0406 (3)	0.0252 (11)
H18	−0.041978	0.704399	−0.001440	0.030*
C19	−0.0794 (5)	0.76391 (16)	−0.3034 (4)	0.0428 (15)
H19A	−0.047412	0.787999	−0.306543	0.064*
H19B	−0.161883	0.766129	−0.310870	0.064*
H19C	−0.074281	0.748835	−0.359219	0.064*
C20	0.6604 (4)	0.68613 (13)	0.3621 (3)	0.0230 (11)
C21	0.4445 (4)	0.70239 (13)	0.3626 (3)	0.0199 (10)
C22	0.7607 (4)	0.62972 (13)	0.5705 (3)	0.0176 (10)
C23	0.8454 (4)	0.65829 (14)	0.5896 (3)	0.0246 (11)
H23	0.820210	0.682797	0.581983	0.030*
C24	0.9660 (4)	0.65016 (16)	0.6197 (3)	0.0326 (13)
H24	1.021532	0.669251	0.632344	0.039*
C25	1.0048 (4)	0.61401 (16)	0.6313 (3)	0.0324 (14)
H25	1.085863	0.608652	0.649885	0.039*
C26	0.9219 (4)	0.58565 (15)	0.6149 (3)	0.0315 (13)
H26	0.947659	0.561191	0.624560	0.038*
C27	0.8012 (4)	0.59378 (13)	0.5841 (3)	0.0234 (11)
H27	0.746189	0.574587	0.572385	0.028*
C28	0.6025 (4)	0.67405 (13)	0.6288 (3)	0.0198 (10)
C29	0.5891 (5)	0.71186 (14)	0.6141 (4)	0.0324 (13)
H29	0.581547	0.721995	0.549531	0.039*
C30	0.5869 (5)	0.73480 (15)	0.6941 (4)	0.0423 (15)
H30	0.577689	0.760181	0.683252	0.051*
C31	0.5983 (5)	0.71993 (16)	0.7901 (4)	0.0358 (13)
H31	0.595101	0.735182	0.843640	0.043*
C32	0.6144 (5)	0.68300 (15)	0.8061 (4)	0.0344 (13)
H32	0.623800	0.673087	0.871411	0.041*
C33	0.6168 (4)	0.65998 (13)	0.7268 (3)	0.0250 (11)
H33	0.628129	0.634720	0.739143	0.030*
C34	0.5268 (4)	0.60132 (12)	0.5404 (3)	0.0150 (10)
H34A	0.552067	0.580369	0.509554	0.018*
H34B	0.549824	0.596640	0.615122	0.018*
C35	0.3097 (4)	0.56202 (12)	0.5064 (3)	0.0160 (10)
C36	0.1925 (4)	0.55998 (13)	0.5041 (3)	0.0218 (11)
H36	0.144301	0.580982	0.488889	0.026*
C37	0.1481 (5)	0.52697 (14)	0.5244 (3)	0.0289 (12)
H37	0.069837	0.525755	0.522178	0.035*
C38	0.2195 (5)	0.49550 (14)	0.5482 (4)	0.0326 (13)
H38	0.189317	0.473274	0.561975	0.039*
C39	0.3353 (5)	0.49742 (13)	0.5512 (3)	0.0283 (12)
H39	0.383817	0.476506	0.567991	0.034*
C40	0.3792 (4)	0.53025 (13)	0.5296 (3)	0.0216 (11)
H40	0.457018	0.531125	0.530449	0.026*
C41	0.3264 (4)	0.63622 (12)	0.5696 (3)	0.0173 (10)
C42	0.2880 (4)	0.67210 (13)	0.5430 (3)	0.0237 (11)
H42	0.276531	0.680940	0.476120	0.028*
C43	0.2662 (5)	0.69537 (14)	0.6159 (4)	0.0348 (13)
H43	0.240436	0.719544	0.597655	0.042*
C44	0.2831 (4)	0.68214 (15)	0.7138 (4)	0.0334 (13)
H44	0.269937	0.697685	0.762477	0.040*
C45	0.3193 (4)	0.64629 (15)	0.7419 (3)	0.0295 (12)
H45	0.328276	0.637497	0.808180	0.035*
C46	0.3421 (4)	0.62350 (13)	0.6706 (3)	0.0203 (10)
H46	0.368134	0.599408	0.689833	0.024*
C47	0.1854 (4)	0.54327 (12)	0.2099 (3)	0.0190 (10)
C48	0.0931 (4)	0.52009 (13)	0.1484 (3)	0.0258 (11)
H48	0.018084	0.530064	0.109826	0.031*
C49	0.1112 (5)	0.48275 (14)	0.1440 (4)	0.0328 (13)
H49	0.047654	0.467587	0.104805	0.039*
C50	0.2232 (5)	0.46751 (15)	0.1974 (4)	0.0367 (14)
H50	0.234927	0.442181	0.194608	0.044*
C51	0.3172 (5)	0.49003 (15)	0.2546 (4)	0.0359 (13)
H51	0.393402	0.480116	0.288828	0.043*
C52	0.2979 (4)	0.52767 (13)	0.2611 (3)	0.0227 (11)
H52	0.361714	0.542713	0.300490	0.027*
C53	0.0484 (4)	0.60009 (13)	0.2734 (3)	0.0186 (10)
C54	0.0450 (4)	0.63486 (13)	0.3149 (3)	0.0231 (11)
H54	0.102310	0.652383	0.316344	0.028*
C55	−0.0423 (4)	0.64388 (14)	0.3541 (3)	0.0281 (12)
H55	−0.043485	0.667238	0.382068	0.034*
C56	−0.1277 (4)	0.61781 (14)	0.3515 (3)	0.0294 (12)
H56	−0.185895	0.623613	0.378580	0.035*
C57	−0.1272 (4)	0.58350 (14)	0.3091 (3)	0.0256 (12)
H57	−0.186297	0.566375	0.305649	0.031*
C58	−0.0381 (4)	0.57431 (14)	0.2713 (3)	0.0235 (11)
H58	−0.036596	0.550782	0.244489	0.028*
C59	0.0822 (4)	0.60429 (12)	0.0805 (3)	0.0188 (10)
C60	−0.0369 (4)	0.61515 (12)	0.0426 (3)	0.0223 (11)
H60	−0.077921	0.616660	0.088156	0.027*
C61	−0.0950 (4)	0.62378 (14)	−0.0626 (3)	0.0298 (12)
H61	−0.175186	0.630961	−0.087322	0.036*
C62	−0.0358 (5)	0.62189 (14)	−0.1314 (3)	0.0312 (12)
H62	−0.074977	0.628004	−0.201958	0.037*
C63	0.0821 (5)	0.61082 (14)	−0.0938 (3)	0.0299 (12)
H63	0.122595	0.609225	−0.139794	0.036*
C64	0.1415 (4)	0.60201 (13)	0.0108 (3)	0.0244 (11)
H64	0.221358	0.594538	0.034901	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01128 (9)	0.01589 (10)	0.01397 (8)	−0.00082 (8)	0.00420 (7)	0.00141 (7)
Fe1	0.0129 (3)	0.0159 (4)	0.0171 (3)	−0.0014 (3)	0.0053 (3)	0.0025 (3)
S1	0.0380 (8)	0.0434 (9)	0.0191 (6)	0.0099 (7)	0.0109 (6)	0.0031 (6)
S2	0.0228 (7)	0.0292 (7)	0.0210 (6)	0.0072 (6)	0.0087 (5)	0.0055 (5)
P1	0.0125 (6)	0.0177 (7)	0.0162 (5)	−0.0015 (5)	0.0035 (5)	0.0004 (5)
P2	0.0119 (6)	0.0134 (6)	0.0149 (5)	0.0001 (5)	0.0043 (5)	0.0015 (5)
P3	0.0129 (6)	0.0200 (7)	0.0159 (5)	−0.0013 (5)	0.0043 (5)	−0.0010 (5)
O1	0.026 (2)	0.026 (2)	0.038 (2)	0.0081 (17)	0.0105 (17)	−0.0009 (16)
O2	0.017 (2)	0.032 (2)	0.051 (2)	−0.0051 (17)	0.0128 (17)	0.0101 (17)
O3	0.0226 (19)	0.0190 (19)	0.0261 (17)	0.0048 (15)	0.0091 (15)	0.0030 (14)
C1	0.018 (3)	0.015 (3)	0.016 (2)	−0.004 (2)	0.0038 (19)	0.0017 (18)
C2	0.021 (3)	0.017 (3)	0.018 (2)	−0.003 (2)	0.009 (2)	−0.0023 (19)
C3	0.012 (2)	0.027 (3)	0.022 (2)	−0.003 (2)	0.008 (2)	−0.003 (2)
C4	0.023 (3)	0.019 (3)	0.022 (2)	−0.001 (2)	0.008 (2)	0.000 (2)
C5	0.028 (3)	0.036 (3)	0.018 (2)	−0.001 (2)	0.006 (2)	−0.009 (2)
C6	0.036 (3)	0.046 (4)	0.029 (3)	−0.002 (3)	0.016 (3)	−0.005 (3)
C7	0.063 (4)	0.029 (3)	0.030 (3)	−0.006 (3)	0.016 (3)	−0.002 (2)
C8	0.045 (4)	0.032 (4)	0.032 (3)	0.002 (3)	0.002 (3)	−0.010 (3)
C9	0.036 (4)	0.045 (4)	0.050 (3)	0.006 (3)	0.016 (3)	−0.013 (3)
C10	0.034 (3)	0.044 (4)	0.034 (3)	−0.007 (3)	0.017 (3)	−0.009 (3)
C11	0.082 (5)	0.040 (4)	0.062 (4)	0.020 (4)	0.015 (4)	−0.003 (3)
C12	0.014 (3)	0.026 (3)	0.023 (2)	−0.002 (2)	0.008 (2)	0.003 (2)
C13	0.019 (3)	0.024 (3)	0.019 (2)	0.001 (2)	0.004 (2)	0.002 (2)
C14	0.016 (3)	0.036 (3)	0.023 (2)	0.004 (2)	0.005 (2)	0.007 (2)
C15	0.026 (3)	0.042 (3)	0.023 (3)	0.001 (3)	0.011 (2)	0.005 (2)
C16	0.026 (3)	0.027 (3)	0.025 (3)	0.002 (2)	0.007 (2)	0.000 (2)
C17	0.015 (3)	0.033 (3)	0.032 (3)	0.003 (2)	0.004 (2)	0.001 (2)
C18	0.019 (3)	0.031 (3)	0.026 (3)	0.002 (2)	0.010 (2)	0.004 (2)
C19	0.035 (3)	0.054 (4)	0.034 (3)	0.004 (3)	0.006 (3)	0.011 (3)
C20	0.020 (3)	0.022 (3)	0.026 (2)	0.005 (2)	0.007 (2)	0.004 (2)
C21	0.016 (3)	0.021 (3)	0.021 (2)	−0.003 (2)	0.006 (2)	0.003 (2)
C22	0.009 (2)	0.027 (3)	0.015 (2)	0.002 (2)	0.0027 (18)	0.0000 (19)
C23	0.020 (3)	0.033 (3)	0.020 (2)	−0.001 (2)	0.006 (2)	0.000 (2)
C24	0.017 (3)	0.056 (4)	0.022 (3)	−0.014 (3)	0.006 (2)	−0.002 (3)
C25	0.010 (3)	0.066 (4)	0.021 (2)	0.002 (3)	0.005 (2)	−0.006 (3)
C26	0.020 (3)	0.040 (3)	0.030 (3)	0.011 (3)	0.005 (2)	−0.011 (2)
C27	0.021 (3)	0.028 (3)	0.019 (2)	0.005 (2)	0.005 (2)	−0.003 (2)
C28	0.013 (2)	0.019 (3)	0.023 (2)	0.000 (2)	0.002 (2)	−0.004 (2)
C29	0.035 (3)	0.024 (3)	0.026 (3)	−0.001 (2)	−0.003 (2)	−0.006 (2)
C30	0.041 (4)	0.025 (3)	0.046 (3)	0.006 (3)	0.001 (3)	−0.011 (3)
C31	0.027 (3)	0.042 (4)	0.038 (3)	0.000 (3)	0.012 (2)	−0.021 (3)
C32	0.032 (3)	0.043 (4)	0.031 (3)	−0.011 (3)	0.016 (2)	−0.010 (3)
C33	0.030 (3)	0.018 (3)	0.028 (3)	−0.001 (2)	0.011 (2)	−0.003 (2)
C34	0.015 (2)	0.016 (3)	0.012 (2)	0.002 (2)	0.0037 (18)	0.0012 (18)
C35	0.019 (3)	0.017 (3)	0.010 (2)	−0.002 (2)	0.0045 (19)	0.0010 (18)
C36	0.021 (3)	0.021 (3)	0.020 (2)	−0.002 (2)	0.004 (2)	0.000 (2)
C37	0.028 (3)	0.032 (3)	0.029 (3)	−0.013 (3)	0.013 (2)	−0.006 (2)
C38	0.048 (4)	0.019 (3)	0.034 (3)	−0.017 (3)	0.018 (3)	−0.001 (2)
C39	0.038 (3)	0.016 (3)	0.029 (3)	0.005 (2)	0.010 (2)	0.000 (2)
C40	0.021 (3)	0.022 (3)	0.022 (2)	0.000 (2)	0.008 (2)	0.003 (2)
C41	0.011 (2)	0.018 (3)	0.023 (2)	−0.005 (2)	0.0069 (19)	−0.0025 (19)
C42	0.027 (3)	0.021 (3)	0.027 (2)	0.000 (2)	0.015 (2)	−0.001 (2)
C43	0.039 (3)	0.020 (3)	0.052 (3)	0.003 (3)	0.025 (3)	−0.006 (3)
C44	0.026 (3)	0.044 (4)	0.036 (3)	−0.009 (3)	0.017 (2)	−0.022 (3)
C45	0.025 (3)	0.044 (4)	0.021 (2)	−0.003 (3)	0.010 (2)	−0.004 (2)
C46	0.015 (2)	0.022 (3)	0.023 (2)	−0.004 (2)	0.0062 (19)	−0.001 (2)
C47	0.022 (3)	0.019 (3)	0.019 (2)	0.000 (2)	0.010 (2)	0.0020 (19)
C48	0.021 (3)	0.027 (3)	0.027 (3)	−0.004 (2)	0.006 (2)	−0.004 (2)
C49	0.037 (3)	0.027 (3)	0.030 (3)	−0.012 (3)	0.008 (3)	−0.007 (2)
C50	0.057 (4)	0.021 (3)	0.031 (3)	0.001 (3)	0.016 (3)	0.000 (2)
C51	0.035 (3)	0.033 (3)	0.035 (3)	0.008 (3)	0.008 (3)	0.004 (3)
C52	0.026 (3)	0.017 (3)	0.022 (2)	−0.004 (2)	0.005 (2)	−0.005 (2)
C53	0.013 (3)	0.027 (3)	0.014 (2)	−0.002 (2)	0.0023 (19)	0.0020 (19)
C54	0.016 (3)	0.028 (3)	0.023 (2)	0.001 (2)	0.005 (2)	0.003 (2)
C55	0.026 (3)	0.032 (3)	0.029 (3)	0.009 (3)	0.014 (2)	0.001 (2)
C56	0.020 (3)	0.046 (4)	0.025 (2)	0.006 (3)	0.011 (2)	0.005 (2)
C57	0.014 (3)	0.036 (3)	0.025 (2)	0.000 (2)	0.006 (2)	0.010 (2)
C58	0.017 (3)	0.033 (3)	0.020 (2)	−0.004 (2)	0.005 (2)	0.002 (2)
C59	0.016 (3)	0.019 (3)	0.018 (2)	−0.003 (2)	0.0011 (19)	−0.0021 (19)
C60	0.018 (3)	0.027 (3)	0.022 (2)	0.006 (2)	0.008 (2)	0.007 (2)
C61	0.020 (3)	0.036 (3)	0.024 (2)	0.007 (2)	−0.002 (2)	−0.001 (2)
C62	0.034 (3)	0.037 (3)	0.015 (2)	0.001 (3)	0.001 (2)	0.001 (2)
C63	0.036 (3)	0.040 (3)	0.017 (2)	0.001 (3)	0.014 (2)	−0.001 (2)
C64	0.016 (3)	0.034 (3)	0.022 (2)	0.001 (2)	0.005 (2)	−0.002 (2)

Geometric parameters (Å, º) top

Pt1—Fe1	2.5697 (6)	C26—C27	1.382 (6)
Pt1—P2	2.2850 (10)	C27—H27	0.9300
Pt1—P3	2.2714 (12)	C28—C29	1.383 (6)
Pt1—C1	2.045 (4)	C28—C33	1.385 (6)
Fe1—P1	2.1966 (12)	C29—H29	0.9300
Fe1—C1	2.162 (4)	C29—C30	1.383 (6)
Fe1—C2	2.119 (4)	C30—H30	0.9300
Fe1—C3	1.932 (5)	C30—C31	1.379 (7)
Fe1—C20	1.777 (5)	C31—H31	0.9300
Fe1—C21	1.789 (5)	C31—C32	1.356 (7)
S1—C4	1.830 (4)	C32—H32	0.9300
S1—C5	1.782 (5)	C32—C33	1.378 (6)
S2—C12	1.808 (4)	C33—H33	0.9300
S2—C13	1.771 (4)	C34—H34A	0.9700
P1—C22	1.839 (4)	C34—H34B	0.9700
P1—C28	1.841 (4)	C35—C36	1.399 (6)
P1—C34	1.842 (4)	C35—C40	1.385 (6)
P2—C34	1.829 (4)	C36—H36	0.9300
P2—C35	1.824 (4)	C36—C37	1.378 (6)
P2—C41	1.819 (4)	C37—H37	0.9300
P3—C47	1.824 (5)	C37—C38	1.388 (7)
P3—C53	1.824 (4)	C38—H38	0.9300
P3—C59	1.830 (4)	C38—C39	1.376 (7)
O1—C21	1.157 (5)	C39—H39	0.9300
O2—C20	1.141 (5)	C39—C40	1.377 (6)
O3—C3	1.216 (5)	C40—H40	0.9300
C1—C2	1.407 (6)	C41—C42	1.380 (6)
C1—C12	1.483 (6)	C41—C46	1.402 (6)
C2—C3	1.464 (6)	C42—H42	0.9300
C2—C4	1.511 (5)	C42—C43	1.404 (6)
C4—H4A	0.9700	C43—H43	0.9300
C4—H4B	0.9700	C43—C44	1.366 (6)
C5—C6	1.384 (6)	C44—H44	0.9300
C5—C10	1.397 (6)	C44—C45	1.376 (7)
C6—H6	0.9300	C45—H45	0.9300
C6—C7	1.367 (7)	C45—C46	1.381 (6)
C7—H7	0.9300	C46—H46	0.9300
C7—C8	1.392 (7)	C47—C48	1.394 (6)
C8—C9	1.373 (7)	C47—C52	1.388 (6)
C8—C11	1.513 (7)	C48—H48	0.9300
C9—H9	0.9300	C48—C49	1.373 (7)
C9—C10	1.381 (7)	C49—H49	0.9300
C10—H10	0.9300	C49—C50	1.382 (7)
C11—H11A	0.9600	C50—H50	0.9300
C11—H11B	0.9600	C50—C51	1.374 (7)
C11—H11C	0.9600	C51—H51	0.9300
C12—H12A	0.9700	C51—C52	1.389 (6)
C12—H12B	0.9700	C52—H52	0.9300
C13—C14	1.394 (6)	C53—C54	1.387 (6)
C13—C18	1.390 (6)	C53—C58	1.389 (6)
C14—H14	0.9300	C54—H54	0.9300
C14—C15	1.387 (6)	C54—C55	1.384 (6)
C15—H15	0.9300	C55—H55	0.9300
C15—C16	1.378 (6)	C55—C56	1.383 (7)
C16—C17	1.395 (6)	C56—H56	0.9300
C16—C19	1.516 (6)	C56—C57	1.371 (7)
C17—H17	0.9300	C57—H57	0.9300
C17—C18	1.373 (6)	C57—C58	1.391 (6)
C18—H18	0.9300	C58—H58	0.9300
C19—H19A	0.9600	C59—C60	1.383 (6)
C19—H19B	0.9600	C59—C64	1.390 (6)
C19—H19C	0.9600	C60—H60	0.9300
C22—C23	1.404 (6)	C60—C61	1.382 (6)
C22—C27	1.376 (6)	C61—H61	0.9300
C23—H23	0.9300	C61—C62	1.378 (6)
C23—C24	1.381 (6)	C62—H62	0.9300
C24—H24	0.9300	C62—C63	1.372 (7)
C24—C25	1.377 (7)	C63—H63	0.9300
C25—H25	0.9300	C63—C64	1.379 (6)
C25—C26	1.388 (7)	C64—H64	0.9300
C26—H26	0.9300

P2—Pt1—Fe1	97.26 (3)	C24—C23—C22	120.3 (5)
P3—Pt1—Fe1	161.46 (3)	C24—C23—H23	119.9
P3—Pt1—P2	100.53 (4)	C23—C24—H24	119.7
C1—Pt1—Fe1	54.44 (12)	C25—C24—C23	120.5 (5)
C1—Pt1—P2	151.36 (12)	C25—C24—H24	119.7
C1—Pt1—P3	107.33 (12)	C24—C25—H25	120.2
P1—Fe1—Pt1	93.50 (4)	C24—C25—C26	119.5 (5)
C1—Fe1—Pt1	50.30 (11)	C26—C25—H25	120.2
C1—Fe1—P1	141.85 (12)	C25—C26—H26	120.0
C2—Fe1—Pt1	73.72 (12)	C27—C26—C25	119.9 (5)
C2—Fe1—P1	130.91 (13)	C27—C26—H26	120.0
C2—Fe1—C1	38.35 (16)	C22—C27—C26	121.3 (5)
C3—Fe1—Pt1	72.18 (13)	C22—C27—H27	119.3
C3—Fe1—P1	88.88 (13)	C26—C27—H27	119.3
C3—Fe1—C1	70.43 (18)	C29—C28—P1	120.7 (3)
C3—Fe1—C2	42.03 (17)	C29—C28—C33	118.0 (4)
C20—Fe1—Pt1	168.78 (14)	C33—C28—P1	121.2 (4)
C20—Fe1—P1	95.66 (14)	C28—C29—H29	119.5
C20—Fe1—C1	119.19 (18)	C28—C29—C30	120.9 (5)
C20—Fe1—C2	95.33 (18)	C30—C29—H29	119.5
C20—Fe1—C3	101.5 (2)	C29—C30—H30	120.1
C20—Fe1—C21	96.5 (2)	C31—C30—C29	119.8 (5)
C21—Fe1—Pt1	87.76 (14)	C31—C30—H30	120.1
C21—Fe1—P1	102.63 (13)	C30—C31—H31	120.1
C21—Fe1—C1	89.16 (18)	C32—C31—C30	119.8 (5)
C21—Fe1—C2	123.33 (18)	C32—C31—H31	120.1
C21—Fe1—C3	157.6 (2)	C31—C32—H32	119.6
C5—S1—C4	102.1 (2)	C31—C32—C33	120.7 (5)
C13—S2—C12	102.2 (2)	C33—C32—H32	119.6
C22—P1—Fe1	115.03 (13)	C28—C33—H33	119.6
C22—P1—C28	100.05 (19)	C32—C33—C28	120.7 (5)
C22—P1—C34	102.6 (2)	C32—C33—H33	119.6
C28—P1—Fe1	121.17 (15)	P1—C34—H34A	109.6
C28—P1—C34	103.71 (19)	P1—C34—H34B	109.6
C34—P1—Fe1	112.02 (13)	P2—C34—P1	110.3 (2)
C34—P2—Pt1	103.14 (13)	P2—C34—H34A	109.6
C35—P2—Pt1	121.79 (13)	P2—C34—H34B	109.6
C35—P2—C34	102.5 (2)	H34A—C34—H34B	108.1
C41—P2—Pt1	121.93 (15)	C36—C35—P2	118.3 (3)
C41—P2—C34	103.99 (19)	C40—C35—P2	123.3 (3)
C41—P2—C35	100.66 (19)	C40—C35—C36	118.5 (4)
C47—P3—Pt1	114.72 (15)	C35—C36—H36	119.9
C47—P3—C53	108.4 (2)	C37—C36—C35	120.2 (5)
C47—P3—C59	100.6 (2)	C37—C36—H36	119.9
C53—P3—Pt1	111.32 (15)	C36—C37—H37	119.8
C53—P3—C59	101.2 (2)	C36—C37—C38	120.4 (5)
C59—P3—Pt1	119.15 (15)	C38—C37—H37	119.8
Pt1—C1—Fe1	75.25 (13)	C37—C38—H38	120.2
C2—C1—Pt1	109.1 (3)	C39—C38—C37	119.6 (5)
C2—C1—Fe1	69.2 (2)	C39—C38—H38	120.2
C2—C1—C12	119.6 (4)	C38—C39—H39	120.0
C12—C1—Pt1	130.5 (3)	C38—C39—C40	120.1 (5)
C12—C1—Fe1	129.0 (3)	C40—C39—H39	120.0
C1—C2—Fe1	72.5 (2)	C35—C40—H40	119.4
C1—C2—C3	111.2 (4)	C39—C40—C35	121.2 (4)
C1—C2—C4	126.2 (4)	C39—C40—H40	119.4
C3—C2—Fe1	62.1 (2)	C42—C41—P2	121.3 (3)
C3—C2—C4	121.9 (4)	C42—C41—C46	118.5 (4)
C4—C2—Fe1	124.8 (3)	C46—C41—P2	120.1 (3)
O3—C3—Fe1	146.8 (3)	C41—C42—H42	119.7
O3—C3—C2	136.5 (4)	C41—C42—C43	120.6 (4)
C2—C3—Fe1	75.8 (3)	C43—C42—H42	119.7
S1—C4—H4A	109.0	C42—C43—H43	120.3
S1—C4—H4B	109.0	C44—C43—C42	119.3 (5)
C2—C4—S1	112.9 (3)	C44—C43—H43	120.3
C2—C4—H4A	109.0	C43—C44—H44	119.3
C2—C4—H4B	109.0	C43—C44—C45	121.3 (4)
H4A—C4—H4B	107.8	C45—C44—H44	119.3
C6—C5—S1	121.9 (4)	C44—C45—H45	120.3
C6—C5—C10	118.4 (5)	C44—C45—C46	119.4 (4)
C10—C5—S1	119.7 (4)	C46—C45—H45	120.3
C5—C6—H6	119.8	C41—C46—H46	119.6
C7—C6—C5	120.4 (5)	C45—C46—C41	120.8 (4)
C7—C6—H6	119.8	C45—C46—H46	119.6
C6—C7—H7	118.9	C48—C47—P3	122.3 (4)
C6—C7—C8	122.2 (5)	C52—C47—P3	120.0 (3)
C8—C7—H7	118.9	C52—C47—C48	117.7 (4)
C7—C8—C11	121.0 (5)	C47—C48—H48	119.5
C9—C8—C7	116.9 (5)	C49—C48—C47	121.0 (5)
C9—C8—C11	122.1 (5)	C49—C48—H48	119.5
C8—C9—H9	118.9	C48—C49—H49	119.8
C8—C9—C10	122.2 (5)	C48—C49—C50	120.5 (5)
C10—C9—H9	118.9	C50—C49—H49	119.8
C5—C10—H10	120.0	C49—C50—H50	120.2
C9—C10—C5	119.9 (5)	C51—C50—C49	119.6 (5)
C9—C10—H10	120.0	C51—C50—H50	120.2
C8—C11—H11A	109.5	C50—C51—H51	120.1
C8—C11—H11B	109.5	C50—C51—C52	119.8 (5)
C8—C11—H11C	109.5	C52—C51—H51	120.1
H11A—C11—H11B	109.5	C47—C52—C51	121.3 (4)
H11A—C11—H11C	109.5	C47—C52—H52	119.3
H11B—C11—H11C	109.5	C51—C52—H52	119.3
S2—C12—H12A	109.1	C54—C53—P3	116.1 (3)
S2—C12—H12B	109.1	C54—C53—C58	118.7 (4)
C1—C12—S2	112.3 (3)	C58—C53—P3	125.1 (4)
C1—C12—H12A	109.1	C53—C54—H54	119.5
C1—C12—H12B	109.1	C55—C54—C53	121.0 (5)
H12A—C12—H12B	107.9	C55—C54—H54	119.5
C14—C13—S2	124.4 (4)	C54—C55—H55	120.3
C18—C13—S2	118.1 (3)	C56—C55—C54	119.4 (5)
C18—C13—C14	117.5 (4)	C56—C55—H55	120.3
C13—C14—H14	119.6	C55—C56—H56	119.8
C15—C14—C13	120.7 (4)	C57—C56—C55	120.5 (4)
C15—C14—H14	119.6	C57—C56—H56	119.8
C14—C15—H15	119.1	C56—C57—H57	120.0
C16—C15—C14	121.7 (4)	C56—C57—C58	120.0 (5)
C16—C15—H15	119.1	C58—C57—H57	120.0
C15—C16—C17	117.2 (4)	C53—C58—C57	120.4 (5)
C15—C16—C19	121.7 (4)	C53—C58—H58	119.8
C17—C16—C19	121.1 (5)	C57—C58—H58	119.8
C16—C17—H17	119.2	C60—C59—P3	122.2 (3)
C18—C17—C16	121.6 (5)	C60—C59—C64	118.9 (4)
C18—C17—H17	119.2	C64—C59—P3	118.9 (3)
C13—C18—H18	119.4	C59—C60—H60	119.9
C17—C18—C13	121.2 (4)	C61—C60—C59	120.2 (4)
C17—C18—H18	119.4	C61—C60—H60	119.9
C16—C19—H19A	109.5	C60—C61—H61	119.6
C16—C19—H19B	109.5	C62—C61—C60	120.9 (5)
C16—C19—H19C	109.5	C62—C61—H61	119.6
H19A—C19—H19B	109.5	C61—C62—H62	120.6
H19A—C19—H19C	109.5	C63—C62—C61	118.8 (4)
H19B—C19—H19C	109.5	C63—C62—H62	120.6
O2—C20—Fe1	178.7 (4)	C62—C63—H63	119.4
O1—C21—Fe1	179.9 (5)	C62—C63—C64	121.1 (4)
C23—C22—P1	116.6 (4)	C64—C63—H63	119.4
C27—C22—P1	124.9 (4)	C59—C64—H64	119.9
C27—C22—C23	118.4 (4)	C63—C64—C59	120.1 (4)
C22—C23—H23	119.9	C63—C64—H64	119.9

Pt1—P2—C34—P1	52.0 (2)	C22—P1—C28—C29	109.4 (4)
Pt1—P2—C35—C36	−87.5 (3)	C22—P1—C28—C33	−70.4 (4)
Pt1—P2—C35—C40	92.7 (4)	C22—P1—C34—P2	−172.0 (2)
Pt1—P2—C41—C42	−5.3 (4)	C22—C23—C24—C25	0.1 (6)
Pt1—P2—C41—C46	177.8 (3)	C23—C22—C27—C26	−0.6 (6)
Pt1—P3—C47—C48	−174.1 (3)	C23—C24—C25—C26	−1.6 (7)
Pt1—P3—C47—C52	2.6 (4)	C24—C25—C26—C27	2.0 (7)
Pt1—P3—C53—C54	34.5 (4)	C25—C26—C27—C22	−0.9 (7)
Pt1—P3—C53—C58	−148.9 (3)	C27—C22—C23—C24	1.0 (6)
Pt1—P3—C59—C60	−122.1 (4)	C28—P1—C22—C23	−58.9 (3)
Pt1—P3—C59—C64	57.8 (4)	C28—P1—C22—C27	124.9 (4)
Pt1—C1—C2—Fe1	−65.2 (2)	C28—P1—C34—P2	84.2 (2)
Pt1—C1—C2—C3	−15.6 (4)	C28—C29—C30—C31	0.1 (8)
Pt1—C1—C2—C4	174.2 (3)	C29—C28—C33—C32	1.8 (7)
Pt1—C1—C12—S2	18.9 (5)	C29—C30—C31—C32	1.4 (8)
Fe1—P1—C22—C23	72.6 (3)	C30—C31—C32—C33	−1.4 (8)
Fe1—P1—C22—C27	−103.6 (3)	C31—C32—C33—C28	−0.2 (8)
Fe1—P1—C28—C29	−18.2 (5)	C33—C28—C29—C30	−1.7 (7)
Fe1—P1—C28—C33	162.1 (3)	C34—P1—C22—C23	−165.5 (3)
Fe1—P1—C34—P2	−48.1 (2)	C34—P1—C22—C27	18.3 (4)
Fe1—C1—C2—C3	49.6 (3)	C34—P1—C28—C29	−144.9 (4)
Fe1—C1—C2—C4	−120.6 (4)	C34—P1—C28—C33	35.3 (4)
Fe1—C1—C12—S2	−86.2 (4)	C34—P2—C35—C36	158.2 (3)
Fe1—C2—C3—O3	−170.8 (6)	C34—P2—C35—C40	−21.6 (4)
Fe1—C2—C4—S1	−172.3 (2)	C34—P2—C41—C42	110.2 (4)
S1—C5—C6—C7	−179.4 (4)	C34—P2—C41—C46	−66.6 (4)
S1—C5—C10—C9	180.0 (4)	C35—P2—C34—P1	179.29 (19)
S2—C13—C14—C15	−175.3 (4)	C35—P2—C41—C42	−143.8 (4)
S2—C13—C18—C17	176.1 (4)	C35—P2—C41—C46	39.3 (4)
P1—C22—C23—C24	−175.4 (3)	C35—C36—C37—C38	0.6 (6)
P1—C22—C27—C26	175.5 (3)	C36—C35—C40—C39	−0.8 (6)
P1—C28—C29—C30	178.5 (4)	C36—C37—C38—C39	−0.1 (7)
P1—C28—C33—C32	−178.5 (4)	C37—C38—C39—C40	−0.8 (7)
P2—C35—C36—C37	−179.9 (3)	C38—C39—C40—C35	1.3 (7)
P2—C35—C40—C39	179.0 (3)	C40—C35—C36—C37	−0.1 (6)
P2—C41—C42—C43	−176.3 (4)	C41—P2—C34—P1	−76.2 (2)
P2—C41—C46—C45	177.1 (3)	C41—P2—C35—C36	51.1 (3)
P3—C47—C48—C49	−179.2 (3)	C41—P2—C35—C40	−128.7 (4)
P3—C47—C52—C51	−179.3 (3)	C41—C42—C43—C44	−0.1 (7)
P3—C53—C54—C55	177.3 (3)	C42—C41—C46—C45	0.2 (7)
P3—C53—C58—C57	−175.9 (3)	C42—C43—C44—C45	−1.1 (8)
P3—C59—C60—C61	179.5 (4)	C43—C44—C45—C46	1.8 (7)
P3—C59—C64—C63	−179.3 (4)	C44—C45—C46—C41	−1.3 (7)
C1—C2—C3—Fe1	−55.2 (3)	C46—C41—C42—C43	0.5 (7)
C1—C2—C3—O3	134.0 (6)	C47—P3—C53—C54	161.5 (3)
C1—C2—C4—S1	−79.3 (5)	C47—P3—C53—C58	−21.8 (4)
C2—C1—C12—S2	−172.5 (3)	C47—P3—C59—C60	111.6 (4)
C3—C2—C4—S1	111.4 (4)	C47—P3—C59—C64	−68.5 (4)
C4—S1—C5—C6	72.5 (4)	C47—C48—C49—C50	−2.6 (7)
C4—S1—C5—C10	−108.5 (4)	C48—C47—C52—C51	−2.3 (6)
C4—C2—C3—Fe1	115.5 (4)	C48—C49—C50—C51	−0.5 (7)
C4—C2—C3—O3	−55.3 (8)	C49—C50—C51—C52	2.1 (7)
C5—S1—C4—C2	−78.1 (4)	C50—C51—C52—C47	−0.6 (7)
C5—C6—C7—C8	−1.0 (8)	C52—C47—C48—C49	3.9 (6)
C6—C5—C10—C9	−0.9 (7)	C53—P3—C47—C48	60.8 (4)
C6—C7—C8—C9	−0.2 (8)	C53—P3—C47—C52	−122.4 (3)
C6—C7—C8—C11	179.4 (5)	C53—P3—C59—C60	0.3 (4)
C7—C8—C9—C10	0.8 (8)	C53—P3—C59—C64	−179.9 (4)
C8—C9—C10—C5	−0.3 (8)	C53—C54—C55—C56	−0.3 (7)
C10—C5—C6—C7	1.6 (7)	C54—C53—C58—C57	0.7 (6)
C11—C8—C9—C10	−178.7 (5)	C54—C55—C56—C57	−0.9 (7)
C12—S2—C13—C14	−36.3 (5)	C55—C56—C57—C58	1.9 (7)
C12—S2—C13—C18	146.7 (4)	C56—C57—C58—C53	−1.9 (7)
C12—C1—C2—Fe1	124.0 (4)	C58—C53—C54—C55	0.4 (6)
C12—C1—C2—C3	173.6 (4)	C59—P3—C47—C48	−44.9 (4)
C12—C1—C2—C4	3.3 (7)	C59—P3—C47—C52	131.8 (3)
C13—S2—C12—C1	−166.4 (3)	C59—P3—C53—C54	−93.2 (3)
C13—C14—C15—C16	−1.5 (8)	C59—P3—C53—C58	83.5 (4)
C14—C13—C18—C17	−1.1 (7)	C59—C60—C61—C62	−0.3 (8)
C14—C15—C16—C17	0.6 (7)	C60—C59—C64—C63	0.6 (7)
C14—C15—C16—C19	179.8 (5)	C60—C61—C62—C63	0.8 (8)
C15—C16—C17—C18	−0.1 (7)	C61—C62—C63—C64	−0.6 (8)
C16—C17—C18—C13	0.4 (8)	C62—C63—C64—C59	−0.1 (8)
C18—C13—C14—C15	1.7 (7)	C64—C59—C60—C61	−0.4 (7)
C19—C16—C17—C18	−179.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.93	2.67	3.316 (6)	128
C34—H34A···O3	0.97	2.62	3.271 (5)	125
C39—H39···O3ⁱⁱ	0.93	2.49	3.239 (6)	138

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1.

Funding information

We are grateful to the Deutsche Forschungsgemeinschaft (DFG) for financial support. LB thanks the Fonds der Chemischen Industrie (FCI) for a doctoral fellowship.

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