Crystal structure and Hirshfeld analysis of trans-di­iodido­bis­[(methyl­sulfan­yl)benzene-κS]platinum(II)

Schmidt, A.; Jourdain, I.; Knorr, M.; Strohmann, C.

doi:10.1107/S2056989023003717

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Volume 79| Part 5| May 2023| Pages 516-520

https://doi.org/10.1107/S2056989023003717

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Crystal structure and Hirshfeld analysis of trans-diiodidobis[(methylsulfanyl)benzene-κS]platinum(II)

Annika Schmidt,^a Isabelle Jourdain,^b Michael Knorr ^b and Carsten Strohmann ^a ^*

^aTU Dortmund University, Institute for Inorganic Chemistry, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany, and ^bInstitut UTINAM CNRS UMR 6213, Equipe "Matériaux et Surfaces Fonctionnels", Université de Franche-Comté, Faculté des Sciences et des Techniques La Bouloie - 16 Route de Gray, 25030 BESANÇON CEDEX, France
^*Correspondence e-mail: carsten.strohmann@tu-dortmund.de

Edited by J. Reibenspies, Texas A & M University, USA (Received 5 April 2023; accepted 24 April 2023; online 28 April 2023)

The title complex, [PtI₂(C₇H₈I₂)₂], represents a further example of a square-planar Pt^II–dithioether complex. It crystallizes in the monoclinic space group P2₁/c. Additional Hirshfeld analyses indicate a C—H⋯π interaction along the [010] axis to be the most important packing factor.

Keywords: crystal structure; Hirshfeld surface analysis; dithioether.

CCDC reference: 2258409

1. Chemical context

Dithioethers are a quite useful class of ligands for various transition-metal complexes and their coordination chemistry is well documented (Murray & Hartley, 1981 ). As a result of the soft character of the sulfur center, they preferably bond to soft transition metals like the coinage metals (Cu, Ag, Au), mercury(II), or catalytically active noble metals such as rhodium(I), iridium(I), palladium(II) or platinum(II). Apart from structural aspects (Marangoni et al., 1995 ) and the investigation of inversion dynamics occurring at the coordinated sulfur atoms (Abel et al., 1984 ), these complexes have been reported to have several applications in homogeneous catalysis (Masdeu-Bulto et al., 2003 ; Arrayás & Carretero, 2011 ). They can form interesting luminescent cluster-like structures (Knorr et al., 2014 ; Peindy et al., 2007 ) and even coordination polymers by coordination to Cu^I and Ag^I (Raghuvanshi et al., 2017 ; Awaleh et al., 2006 ). Depending on the metal coordination sphere and the remaining ligands, the preparation of dithioether complexes may yield different isomers. In particular, the isomerism of chalcogenoether complexes with palladium and platinum has been intensively investigated (Vigo et al., 2006 ) and the presence of both trans- and cis-isomers in solution and the solid state were proven. The clarification of the trans–cis isomerism is therefore of importance.

In the past, our groups have investigated the coordination of chelating dithioethers such as the vinylic ferrocenyl-dithioether Z-[(ArS)(H)C=C(SAr)-Fc] or the silylated compounds (PhSCH₂)₂SiPh₂ and PhSCH₂Si(Me)-Si(Me)CH₂SPh₂ yielding [Fc-{C(S-p-tolyl)=C(S-p-tolyl)(H)}PtCl₂], cis-[PtCl₂{(PhSCH₂)₂Si₂Me₄}] and cis-[PtCl₂{(PhSCH₂)₂SiPh₂}] and converted them via metathesis in the presence of NaI to their corresponding diiodo derivatives (Clement et al., 2007 ; Knorr et al., 2004 ; Peindy et al., 2006 ). We have also shown that the tetrakis(thioether) (PhSCH₂)₄Si can be ligated on HgBr₂ in a chelating manner (Peindy et al., 2005 ). In a similar manner, we also prepared, as shown in Fig. 1, the complex cis-[PtI₂{(PhSCH₂)₂Si(CH₂SPh}₂]. When attempting to recrystallize this poorly soluble compound from hot toluene, partial cleavage of the Si—CH₂Ph bond occurred, yielding trans-[PtI₂(SMePh)₂] 1, albeit in a quite low yield of 10%. Alternatively, this air-stable complex could be prepared in a much improved yield of 80% by reaction of bis(benzonitrile)diiodoplatinum with 2 equivalents of methyl phenyl sulfide (thioanisol) MeSPh using dichloromethane as solvent. This compound was characterized by NMR spectroscopy in solution and exhibits a singlet resonance for the two magnetically equivalent methyl groups at δ 3.01 ppm, flanked by ¹⁹⁵Pt satellites due to a ³J_PtH coupling of 48 Hz. Furthermore, we report herein on the solid-state structure and structural analysis of trans-diiodidobis[(methylsulfanyl)benzene-κS]platinum(II) (1). In addition, the results of a Hirshfeld analysis of the intermolecular interactions are presented.

Figure 1
Synthesis scheme for trans-PtI₂(SMePh)₂] (1).

2. Structural commentary

trans-Diiodidobis[(methylsulfanyl)benzene-κS]platinum(II) (1) crystallizes from dichloromethane in the monoclinic crystal system, space group P2₁/c. The molecular structure of 1 is presented in Figs. 2 and 3 and selected bond lengths and bond angles are given in Table 1. The asymmetric unit contains half a molecule of 1, which shows C_2h symmetry. The distance from the coordinating iodine center I1 to Pt1 is 2.61205 (15) Å, showing a slight elongation with respect to its educt structure trans-[PtI₂(NCPh)₂] (2) (2.6052 (8) Å; Viola et al., 2018 ). The distance from the coordinating sulfur atom S1 to Pt1 is 2.3183 (5) Å. The S1—Pt1 bond is 0.015 Å longer than in the analogous chlorine compound trans-[PtCl₂(SMePh)₂] (3) reported by Ahlgrén (CSD LEQSUW; Vigo et al., 2006). This elongation may be explained by the thermodynamic trans-effect of the opposite halide ligand. Therefore, similar compounds with iodido ligands such as trans-[PtI₂(SMe₂)₂] (4) (CSD RAYNOU; Lövqvist et al., 1996 ) and trans-[PtI₂(tetrahydrothiophene)₂] (5) (CSD SIRPAK; Oskarsson et al., 1990 ) show S—Pt bond lengths in the same range at 2.310 (2) and 2.310 (1) Å, respectively. Both complexes also have similar bond lengths for the Pt—I bond [2.6039 (8) Å in 4 and 2.606 (1) Å in 5]. The chelate complexes cis-diiodo-[1,2-bis(phenylsulfanyl)ethane]platinum(II) (CSD ZAJWUC; Marangoni et al., 1995) and cis-(1,4-dithiane-S,S′)diiodoplatinum(II) (CSD HUFQAA; Johansson & Engelbrecht, 2001 ) are reported to display Pt—I bond lengths of 2.606 (1) and 2.6035 (5) Å, respectively, and somewhat shorter mean Pt—S bond lengths of 2.265 (2) and 2.2751 (16) Å, respectively.

Table 1
Selected geometric parameters (Å, °)

Pt1—I1	2.6121 (2)	S1—C2	1.782 (2)
Pt1—S1	2.3183 (5)	S1—C1	1.800 (2)

I1ⁱ—Pt1—I1	180.0	S1—Pt1—I1	85.641 (14)
S1—Pt1—I1ⁱ	94.359 (14)	C2—S1—C1	103.46 (11)
Symmetry code: (i) .

Figure 2
Molecular structure of 1 in the unit cell.

Figure 3
Asymmetric unit of 1 with labeled atoms.

All further bonds have characteristic dimensions (Allen et al., 1987 ). The coordination sphere around the platinum center is square-planar. The angles I1—Pt1—I1 and S1—Pt1—S1 are 180°. However, the angle I1—Pt1—S1 of 85.641 (14)° is somewhat more acute. This slight deviation from the ideal angle of 90° is also reported for the chlorido derivative 3 and the dimethyl sulfide analog 4, as well as in the tetrahydrothiophene analog 5. The sulfur center shows a distorted tetrahedral environment with angles C1—S1—Pt1 = 111.00 (8)°, C2—S1—Pt1 = 104.52 (7)° and C2—S1—C1 = 103.46 (11)°.

3. Supramolecular features

While a repetition of the molecular structure of 1 can be seen along the [100] axis and the [001] axis, as shown in Fig. 4, the crystal packing along the [010] axis is defined by C—H⋯π interactions of the C2–C7 phenyl ring and H1Bⁱ [symmetry code: (i) x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z] with a distance between the phenyl ring and H1Bⁱ of 2.5377 (10) Å (Fig. 5). This interaction can also be visualized by a Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) generated by CrystalExplorer21 (Spackman et al., 2021 ). The Hirshfeld surface mapped over d_norm in the range from −0.0074 to 1.1829 a.u. is shown in Fig. 6, with the close contact between H1Bⁱ and the C2–C7 plane indicated by the red spot. The contributions of the different types of intermolecular interactions for 1 are shown in the two-dimensional fingerprint plots (McKinnon et al., 2007 ) in Fig. 7. The contribution of the H⋯H interactions, with a value of 39.8%, has the largest share of the crystal packing of 1. The remaining hydrogen–heteronuclear interactions have a smaller share with a 15.7% contribution for I⋯H, a 14.4% contribution for C⋯H and a 3.6% contribution for S⋯H. The heteronuclear I⋯H and C⋯H interactions appear as spikes.

Figure 4
The packing of the solid-state structure of 1 along the [100] axis.

Figure 5
The packing of the solid-state structure of 1 along the [010] axis [symmetry code: (i) x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z].

Figure 6
Hirshfeld surface analysis of 1 showing close contacts in the crystal. The π-interaction between hydrogen atom H1Bⁱ and the phenyl ring C2–C7 is indicated by the red spot [symmetry code: (i) x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z].

Figure 7
Two-dimensional fingerprint plots for compound 1, showing (a) all contributions, and (b)–(d) delineated into the contributions of atoms within specific interacting pairs (blue areas).

4. Database survey

By a search in the Cambridge Crystallographic Database (WebCSD, November 2022; Groom et al., 2016 ), various structures of dihalide transition-metal complexes with the same ligand motif as 1 were found. To compare the most similar structures, only dihalide transition metal complexes with the bis[(methylsulfanyl)benzene] ligand and its oxidized derivative are focused on now. The already compared structure trans-dichloro-bis[methyl(phenyl)sulfanyl]platinum (LEQSUW; Vigo et al., 2006) has been published, as well as its palladium derivative with (SARWEP; Oilunkaniemi et al., 2006 ) and without (LEQSOQ; Vigo et al., 2006) inserted benzene. In addition, cis-dichlorobis(methylphenylsulfoxide)palladium has been published independently by two different research groups [JISWUD (Antolini et al., 1991 ) and JISWUD01 (Gama de Almeida et al., 1992 )]. Further examples of PtI₂ thioether complexes are cis-diiodo-(1,4,7-trithiacyclononane-S,S′)platinum(II) (ACUXAX; Grant et al., 2001 ), diiodo-(2,9-dimethyl-1,10-phenanthroline)(dimethylsulfide)platinum(II) (BERTIC; Fanizzi et al., 2004 ), and diiodo-(5-phenyl-1-thia-5-phosphacyclo-octane-P,S)platinum(II) (KEJHEM; Toto et al., 1990 ).

Similar complexes were also structurally characterized by our research groups and include cis-[PtBr₂{(PhSCH₂)₂SiPh₂}] (ECOHAG; Knorr et al., 2004) and cis-[PtI₂{(PhSCH₂)₂SiPh₂}]·DCM (ECOHIO, Knorr et al., 2004), which were determined in order to investigate the trans-influence of different halide ligands on the Pt—S bond. Further examples of dithioether complexes stemming from our laboratories are cis-[PtCl₂{(PhSCH₂)₂Si₂Me₄}] (MEDYOK; Peindy et al., 2006) and cis-[PtI₂{(PhSCH₂)₂Si₂Me₄}]·DCM (MEDZIF; Peindy et al., 2006).

5. Synthesis and crystallization

trans-Diiodobis[(methylsulfanyl)benzene]platinum (1) was synthesized by adding methylphenyl sulfide (37 mg, 0.30 mmol, 1.50 eq.) dissolved in 0.5 mL of dichloromethane via a microsyringe to a solution of bis(benzonitrile)diiodoplatinum (65 mg, 0.10 mmol, 1.00 eq.) in dichloromethane (3 mL) and stirring overnight at room temperature. trans-Diiodobis[(methylsulfanyl)benzene]platinum (1, 557 mg, 0.80 mmol, 80%) was isolated as red crystals after layering with heptane.

Calculated for C₁₄H₁₆I₂PtS₂ (697.30 g mol⁻¹): C, 24.11; H, 2.32; S, 9.20. Found: C, 23.92; H, 2.21; S, 9.05%.

¹H NMR (400MHz, CDCl₃): δ = 3.01 (s, ³J_PtH = 48 Hz, 6H; CH₃), 7.05–7.73 (m, 10H; phenyl) ppm.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically (C—H = 0.95–1.00 Å) and were refined using a riding model, with U_iso(H) = 1.2U_eq(C) for CH₂ and CH hydrogen atoms and U_iso (H) = 1.5U_eq(C) for CH₃ hydrogen atoms.

Table 2
Experimental details

Crystal data
Chemical formula	[PtI₂(C₇H₈I)₂]
M_r	697.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.5796 (3), 9.5104 (3), 9.7960 (3)
β (°)	107.645 (1)
V (Å³)	850.48 (5)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	12.11
Crystal size (mm)	0.31 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.263, 0.498
No. of measured, independent and observed [I > 2σ(I)] reflections	27554, 4125, 4033
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.833

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.053, 1.17
No. of reflections	4125
No. of parameters	89
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.26, −1.80
Computer programs: APEX2 and SAINT V8.38A (Bruker, 2018 ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2258409

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989023003717/jy2030sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003717/jy2030Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2018); cell refinement: SAINT V8.38A (Bruker, 2018); data reduction: SAINT V8.38A (Bruker, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

trans-Diiodidobis[(methylsulfanyl)benzene-κS]platinum(II) top

Crystal data top

[PtI₂(C₇H₈I)₂]	F(000) = 632
M_r = 697.28	D_x = 2.723 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5796 (3) Å	Cell parameters from 9775 reflections
b = 9.5104 (3) Å	θ = 3.1–36.3°
c = 9.7960 (3) Å	µ = 12.11 mm⁻¹
β = 107.645 (1)°	T = 100 K
V = 850.48 (5) Å³	Prism, red
Z = 2	0.31 × 0.25 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	4125 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	4033 reflections with I > 2σ(I)
HELIOS mirror optics monochromator	R_int = 0.038
Detector resolution: 10.4167 pixels mm^-1	θ_max = 36.3°, θ_min = 2.2°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −15→15
T_min = 0.263, T_max = 0.498	l = −16→16
27554 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)] = 0.021	H-atom parameters constrained
wR(F²) = 0.053	w = 1/[σ²(F_o²) + (0.0193P)² + 1.6484P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.002
4125 reflections	Δρ_max = 2.26 e Å⁻³
89 parameters	Δρ_min = −1.79 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.

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

	x	y	z	U_iso*/U_eq
Pt1	0.500000	0.500000	0.500000	0.01069 (3)
I1	0.67448 (2)	0.70668 (2)	0.48539 (2)	0.01650 (4)
S1	0.66656 (6)	0.45396 (6)	0.72234 (6)	0.01359 (8)
C3	0.7382 (3)	0.1669 (2)	0.7476 (2)	0.0159 (3)
H3	0.668801	0.154647	0.798352	0.019*
C7	0.8623 (2)	0.3176 (2)	0.6213 (3)	0.0168 (4)
H7	0.876638	0.407868	0.586351	0.020*
C2	0.7595 (2)	0.2989 (2)	0.6957 (2)	0.0134 (3)
C1	0.5743 (3)	0.3994 (3)	0.8486 (2)	0.0188 (4)
H1A	0.518020	0.478370	0.868893	0.028*
H1B	0.646855	0.368646	0.937513	0.028*
H1C	0.507882	0.321330	0.807968	0.028*
C4	0.8199 (3)	0.0527 (3)	0.7244 (3)	0.0200 (4)
H4	0.806058	−0.037609	0.759612	0.024*
C5	0.9216 (3)	0.0705 (3)	0.6501 (3)	0.0216 (4)
H5	0.976478	−0.007512	0.633993	0.026*
C6	0.9426 (3)	0.2037 (3)	0.5991 (3)	0.0209 (4)
H6	1.012472	0.216130	0.549005	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01172 (5)	0.00914 (5)	0.01237 (5)	0.00010 (3)	0.00539 (3)	0.00002 (3)
I1	0.01712 (6)	0.01357 (6)	0.02033 (7)	−0.00397 (4)	0.00794 (5)	0.00006 (4)
S1	0.0149 (2)	0.0124 (2)	0.01360 (19)	−0.00016 (15)	0.00455 (16)	−0.00055 (15)
C3	0.0176 (8)	0.0150 (8)	0.0162 (8)	0.0008 (7)	0.0067 (7)	0.0012 (7)
C7	0.0142 (8)	0.0170 (9)	0.0205 (9)	−0.0018 (7)	0.0073 (7)	−0.0004 (7)
C2	0.0135 (8)	0.0132 (8)	0.0134 (8)	−0.0002 (6)	0.0039 (6)	−0.0010 (6)
C1	0.0226 (10)	0.0214 (10)	0.0147 (8)	0.0047 (8)	0.0092 (7)	0.0018 (7)
C4	0.0229 (10)	0.0164 (9)	0.0206 (10)	0.0038 (7)	0.0063 (8)	0.0029 (7)
C5	0.0194 (10)	0.0210 (10)	0.0244 (11)	0.0073 (8)	0.0065 (8)	−0.0001 (8)
C6	0.0149 (9)	0.0243 (11)	0.0257 (11)	0.0010 (8)	0.0094 (8)	−0.0012 (8)

Geometric parameters (Å, º) top

Pt1—I1	2.6121 (1)	C7—C2	1.403 (3)
Pt1—I1ⁱ	2.6120 (1)	C7—C6	1.383 (3)
Pt1—S1ⁱ	2.3183 (5)	C1—H1A	0.9800
Pt1—S1	2.3183 (5)	C1—H1B	0.9800
S1—C2	1.782 (2)	C1—H1C	0.9800
S1—C1	1.800 (2)	C4—H4	0.9500
C3—H3	0.9500	C4—C5	1.392 (4)
C3—C2	1.393 (3)	C5—H5	0.9500
C3—C4	1.397 (3)	C5—C6	1.398 (4)
C7—H7	0.9500	C6—H6	0.9500

I1ⁱ—Pt1—I1	180.0	C7—C2—S1	115.60 (17)
S1ⁱ—Pt1—I1	94.358 (14)	S1—C1—H1A	109.5
S1—Pt1—I1ⁱ	94.359 (14)	S1—C1—H1B	109.5
S1—Pt1—I1	85.641 (14)	S1—C1—H1C	109.5
S1ⁱ—Pt1—I1ⁱ	85.643 (14)	H1A—C1—H1B	109.5
S1—Pt1—S1ⁱ	180.0	H1A—C1—H1C	109.5
C2—S1—Pt1	104.52 (7)	H1B—C1—H1C	109.5
C2—S1—C1	103.46 (11)	C3—C4—H4	119.8
C1—S1—Pt1	111.00 (8)	C5—C4—C3	120.4 (2)
C2—C3—H3	120.3	C5—C4—H4	119.8
C2—C3—C4	119.3 (2)	C4—C5—H5	120.1
C4—C3—H3	120.3	C4—C5—C6	119.7 (2)
C2—C7—H7	120.2	C6—C5—H5	120.1
C6—C7—H7	120.2	C7—C6—C5	120.4 (2)
C6—C7—C2	119.6 (2)	C7—C6—H6	119.8
C3—C2—S1	123.88 (17)	C5—C6—H6	119.8
C3—C2—C7	120.5 (2)

Pt1—S1—C2—C3	−107.26 (19)	C1—S1—C2—C7	−168.90 (18)
Pt1—S1—C2—C7	74.82 (17)	C4—C3—C2—S1	−178.09 (18)
C3—C4—C5—C6	0.4 (4)	C4—C3—C2—C7	−0.3 (3)
C2—C3—C4—C5	0.0 (4)	C4—C5—C6—C7	−0.5 (4)
C2—C7—C6—C5	0.2 (4)	C6—C7—C2—S1	178.21 (19)
C1—S1—C2—C3	9.0 (2)	C6—C7—C2—C3	0.2 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Selected geometric parameters for compound 1 (Å, °) top

Pt1–I1	2.61205 (15)	I1–Pt1–I1i	180.0
Pt1–S1	2.3183 (5)	S1–Pt1–I1	85.641 (14)
S1–C2	1.782 (2)	S1–Pt1–I1i	94.359 (14)
S1–C1	1.800 (2)	C2–S1–C1	103.46 (11)

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