research communications
Crystal structures of (Z)-(ethene-1,2-diyl)bis(diphenylphosphine sulfide) and its complex with PtII dichloride
aDepartment of Chemistry, Grand Valley State University, Allendale, MI 49401, USA, and bCenter for Crystallographic Research, Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA
*Correspondence e-mail: biross@gvsu.edu
The crystal structures of (Z)-(ethene-1,2-diyl)bis(diphenylphosphine sulfide), C26H22P2S2 (I), along with its complex with PtII dichloride, dichlorido[(Z)-(ethene-1,2-diyl)bis(diphenylphosphine sulfide)-κ2S,S′]platinum(II), [PtCl2(C26H22P2S2)] (II), are described here. Compound I features P=S bond lengths of 1.9571 (15) and 1.9529 (15) Å, with a torsion angle of 166.24 (7)° between the two phosphine sulfide groups. The crystal of compound I features both intramolecular C—H⋯S hydrogen bonds and π–π interactions. Molecules of compound I are held together with intermolecular π–π and C—H⋯π interactions to form chains that run parallel to the z-axis. The intermolecular C—H⋯π interaction has a H⋯Cg distance of 2.63 Å, a D⋯Cg distance of 3.573 (5) Å and a D—H⋯Cg angle of 171° (where Cg refers to the centroid of one of the phenyl rings). These chains are linked by relatively long C—H⋯S hydrogen bonds with D⋯A distances of 3.367 (4) and 3.394 (4) Å with D—H⋯A angles of 113 and 115°. Compound II features Pt—Cl and Pt—S bond lengths of 2.3226 (19) and 2.2712 (19) Å, with a P=S bond length of 2.012 (3) Å. The PtII center adopts a square-planar geometry, with Cl—Pt—Cl and S—Pt—S bond angles of 90.34 (10) and 97.19 (10)°, respectively. Molecules of compound II are linked in the crystal by intermolecular C—H⋯Cl and C—H⋯S hydrogen bonds.
1. Chemical context
The diphosphine compound cis-bis(diphenylphosphino)ethylene (cis-dppe, Fig. 1) has been used by many research groups as a ligand in organometallic chemistry (Hirano & Miura, 2017; Price & Walton, 1987). While the bisphosphine oxide derivative has found use in the coordination chemistry of both d-block and f-block metals (Jarrett & Sadler, 1991; Banda & Pritchard, 2008; Morse, et al., 2016), the bisphosphine sulfide and bisphosphineselenide derivatives have been less studied. Our group is interested in developing new organic compounds that can facilitate the separation of actinide (An) metals from lanthanide (Ln) metals in liquid–liquid extraction processes (Gorden et al., 2013). Since the An metals have a greater preference for soft-donor atoms than the Ln metals (Cotton, 2006), there have been some successes with the use of phosphine sulfide compounds as actinide extraction agents (e.g. Cyanex 301; Zhu et al., 1996). To this end, we prepared compound I from cis-dppe using elemental sulfur (Fig. 1; Aguiar & Daigle, 1964; Duncan & Gallagher, 1981). Unfortunately, our efforts in this area were plagued by the ease of isomerization of the cis-alkene to a trans-alkene when the systems were heated for even short lengths of time. In an effort to understand the ability of this ligand to form complexes with metals, we also reacted compound I with Pt(PhCN)2Cl2 to give compound II.
2. Structural commentary
The structure of compound I was solved in the orthorhombic P212121. The molecular structure of this compound is shown in Fig. 2 along with the atom numbering scheme. The structure of disulfide I has P=S bond lengths of 1.9571 (15) and 1.9529 (15) Å, P—C bond lengths that range from 1.804 (4) to 1.824 (4) Å and a C=C bond length of 1.338 (5) Å. The P=S bonds are oriented in opposite directions with a S1—P1—P2—S2 torsion angle of 166.24 (7)°. The τ4 descriptor for fourfold coordination around both phosphorus atoms P1 and P2 is 0.94, indicating a near tetrahedral geometry of the phosphine sulfide groups (where 0.00 = square-planar, 0.85 = trigonal–pyramidal, and 1.00 = tetrahedral; Yang et al., 2007). The bond angles around both phosphorus atoms range from 100.75 (18) to 115.48 (14)°, with the largest angles involving the sulfur atom. One intramolecular π–π interaction is present between the C9–C14 and C21–C26 rings with an intercentroid distance of 3.737 (3) Å, slippage of 3.370 Å and a dihedral angle of 5.6 (2)°. Both C8(H8) and C10(H10) are engaged in intramolecular C—H⋯S hydrogen bonds with S1 (Ghosh et al., 2020; Table 1). These interactions have D⋯A distances of 3.344 (4) and 3.360 (4) Å with D—H⋯A dihedral angles of 113 and 116°, respectively (Table 1, Fig. 3). In a similar fashion, S2 hosts two intramolecular C—H hydrogen bonds with C20(H20) and C26(H26). These interactions have D⋯A distances of 3.367 (4) and 3.394 (4) Å with D—H⋯A dihedral angles of 113 and 115°, respectively. The for this structure is −0.10 (5) (Parsons et al., 2013).
For the PtII complex II, the structure was solved in the orthorhombic Fdd2. Since the entire molecule straddles a twofold symmetry axis, the is composed of half of the molecule. The complete molecular structure of compound II is shown in Fig. 4 along with the atom-numbering scheme. The Pt—Cl and Pt—S bond lengths are 2.3226 (19) and 2.2712 (19) Å, respectively. The Cl1—Pt1—Cl1i and S1—Pt1—S1i bond angles are 90.34 (10) and 97.19 (10)°, respectively [symmetry code: (i) −x + 1, −y + 1, z]. The τ4 descriptor for fourfold coordination around the PtII center is 0.05, indicating a nearly perfect square-planar orientation of the sulfur and chlorine atoms around the metal (Yang et al., 2007). The P=S bond length is 2.012 (3) Å, which is slightly longer than what was observed for compound I. The complex has P—C bond lengths that range from 1.799 (8) to 1.816 (9) Å, with a C=C bond length of 1.312 (18) Å. The τ4 descriptor for fourfold coordination of the phosphorus atom P1 is 0.91, indicating a slightly distorted tetrahedral geometry of the groups bonded to this atom, and that this tetrahedron is more distorted than what was observed for compound I.
3. Supramolecular features
Molecules of compound I are held together in the crystal by intermolecular π–π and C—H⋯π interactions (Table 1 and Fig. 3). Ring C9–C14 is engaged in an intermolecular π–π interaction with a screw-related C21–C26 ring (symmetry code: −x + , −y + 1, z − ). The centroid–centroid distance of this interaction is 3.896 (3) Å, with a slippage of 3.598 Å and a dihedral angle of 10.80 (14) °. Hydrogen atom C11(H11) is engaged in an intermolecular C—H⋯π interaction with ring C15–C20 (symmetry code −x + , −y + 1, z + ) with an H⋯Cg distance of 2.63 Å, a D⋯Cg distance of 3.573 (5) Å and a D—H⋯Cg angle of 171° (Cg is the centroid of the C15–C20 ring). Together, these intermolecular π–π and C—H⋯π interactions link the molecules into chains that propagate parallel to the z-axis (Fig. 5). Two potential intermolecular C—H⋯S interactions exist between C1(H1) and C7(H7) and S2. These interactions have relatively long D⋯A distances of 3.742 (4) and 3.561 (5) Å with D—H⋯A angles of 155 and 135°, respectively. These hydrogen-bonding interactions occur between the supramolecular chains of compound I.
Molecules of compound II are held together by C—H⋯Cl (Aullón et al., 1998) and C—H⋯S hydrogen bonds (Ghosh et al., 2020; Table 2 and Fig. 6). The C—H⋯Cl interaction is between hydrogen atom C1(H1) and Cl1 and has a D⋯A distance of 3.515 (10) Å with a D—H⋯A angle of 141° (symmetry code: −x + 1, −y + 1, z + 1). Sulfur atom S1 hosts the other intermolecular hydrogen bond with atom C3(H3) (symmetry code: x + , −y + , z + ). This interaction has a slightly longer D⋯A distance of 3.538 (9) with a D—H⋯A angle of 133°. The intermolecular C—H⋯Cl interactions form chains of compound II that run parallel to the z-axis. These chains are then linked into a three-dimensional network through the intermolecular C—H⋯S hydrogen bonds.
4. Database survey
A search of the Cambridge Structural Database (CSD version 5.42, Sep. 2021; Groom et al., 2016) for structures similar to compound I resulted in 17 hits. The majority of these hits were metal–ligand complexes, where the ligand was a triazole ring bearing two diphenylphosphine sulfide groups. Crystal structures of this ligand bonded to copper(II), zinc(II), palladium(II), and cadmium(II) were reported (KOBJOC, KOBKAP, KOBKUJ, KOBKIX; Pastor-Medrano, et al., 2014), along with complexes containing zirconium(IV) and hafnium(IV) (PUKNAM, PUKNEQ; Bernabe-Pablo et al., 2016). A structure closely related to compound I, where the alkene bears a phenyl ring and is bonded to the phosphine sulfide groups with a trans relationship, has also been deposited in the CSD as a private communication (GOLXAI; Rybakov and Afanas'ev, 2010).
5. Synthesis and crystallization
Compound I: cis-dppe (500 mg, 1.25 mmol) and elemental sulfur (S8, 80 mg, 0.31 mmol) were combined in a round-bottom flask and dissolved in tetrahydrofuran (5 mL). The reaction mixture was stirred for three h at room temperature. The solvent was removed under reduced pressure to give a white, gelatinous solid. The crude product was recrystallized from benzene (5 mL) at 333 K and isolated by vacuum filtration with a Hirsch funnel to give a white solid. Analysis of the solid by 31P NMR (CDCl3) showed that the target compound I was present along with trans-dppeS2 and unreacted starting material. Single crystals of compound I grew serendipitously upon slow evaporation of this solution. 31P NMR (CDCl3, 121 MHz): Compound I: 32.3 ppm; trans-dppeS2: 36.6 ppm; cis-dppe: −22 ppm.
Compound II: Equimolar amounts of compound I (10.0 mg, 0.022 mmol) and Pt(PhCN)2Cl2 (10.4 mg, 0.022 mmol) were combined in a small vial and dissolved in 1 mL CDCl3. Crystals of compound II formed serendipitously via slow evaporation of the solvent.
6. Refinement
Crystal data, data collection and structure . For compounds I and II, all hydrogen atoms bonded to carbon atoms were placed in calculated positions and refined as riding: C—H = 0.95–1.00 Å with Uiso(H) = 1.2Ueq(C) for vinylic and aromatic hydrogen atoms.
details are summarized in Table 3
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Supporting information
https://doi.org/10.1107/S2056989022011847/pk2674sup1.cif
contains datablocks I, II. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022011847/pk2674Isup4.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989022011847/pk2674IIsup5.hkl
For both structures, data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013). Program(s) used to solve structure: olex2.solve (Bourhis et al., 2015) for (I); SHELXS (Sheldrick, 2008) for (II). For both structures, program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009; Bourhis et al., 2015); software used to prepare material for publication: CrystalMaker (Palmer, 2007).C26H22P2S2 | Dx = 1.335 Mg m−3 |
Mr = 460.49 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 7213 reflections |
a = 12.315 (3) Å | θ = 2.2–25.3° |
b = 13.092 (3) Å | µ = 0.38 mm−1 |
c = 14.211 (4) Å | T = 173 K |
V = 2291.2 (10) Å3 | Chunk, yellow |
Z = 4 | 0.22 × 0.17 × 0.11 mm |
F(000) = 960 |
Bruker APEXII CCD diffractometer | 3676 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.057 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 25.4°, θmin = 2.1° |
Tmin = 0.655, Tmax = 0.745 | h = −14→14 |
18678 measured reflections | k = −15→15 |
4213 independent reflections | l = −17→17 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0374P)2 + 0.5294P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.088 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.37 e Å−3 |
4213 reflections | Δρmin = −0.20 e Å−3 |
271 parameters | Absolute structure: Flack x determined using 1430 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: −0.10 (5) |
Primary atom site location: iterative |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.55697 (10) | 0.38129 (8) | 0.13055 (8) | 0.0420 (3) | |
S2 | 0.39195 (10) | 0.80901 (8) | −0.04312 (8) | 0.0398 (3) | |
P1 | 0.53899 (8) | 0.52703 (8) | 0.15692 (7) | 0.0300 (3) | |
P2 | 0.44444 (9) | 0.67175 (8) | −0.07181 (7) | 0.0281 (2) | |
C1 | 0.6036 (3) | 0.6052 (3) | 0.0686 (3) | 0.0306 (9) | |
H1 | 0.677946 | 0.617631 | 0.082123 | 0.037* | |
C2 | 0.5716 (3) | 0.6497 (3) | −0.0115 (3) | 0.0297 (9) | |
H2 | 0.631332 | 0.676857 | −0.045572 | 0.036* | |
C3 | 0.6119 (3) | 0.5670 (3) | 0.2624 (3) | 0.0299 (9) | |
C4 | 0.6408 (4) | 0.6679 (3) | 0.2775 (3) | 0.0415 (11) | |
H4 | 0.621187 | 0.718677 | 0.232846 | 0.050* | |
C5 | 0.6981 (4) | 0.6949 (4) | 0.3576 (3) | 0.0476 (12) | |
H5 | 0.717475 | 0.764283 | 0.367629 | 0.057* | |
C6 | 0.7273 (3) | 0.6222 (4) | 0.4226 (3) | 0.0397 (10) | |
H6 | 0.767874 | 0.640847 | 0.476863 | 0.048* | |
C7 | 0.6973 (3) | 0.5225 (4) | 0.4085 (3) | 0.0445 (12) | |
H7 | 0.716344 | 0.472267 | 0.453822 | 0.053* | |
C8 | 0.6397 (3) | 0.4940 (3) | 0.3292 (3) | 0.0382 (10) | |
H8 | 0.619223 | 0.424702 | 0.320333 | 0.046* | |
C9 | 0.3997 (3) | 0.5681 (3) | 0.1732 (3) | 0.0285 (9) | |
C10 | 0.3184 (3) | 0.4950 (3) | 0.1773 (3) | 0.0358 (10) | |
H10 | 0.336454 | 0.424670 | 0.171665 | 0.043* | |
C11 | 0.2115 (3) | 0.5236 (4) | 0.1896 (3) | 0.0398 (11) | |
H11 | 0.155785 | 0.473502 | 0.191199 | 0.048* | |
C12 | 0.1863 (4) | 0.6263 (4) | 0.1997 (3) | 0.0421 (11) | |
H12 | 0.112958 | 0.646480 | 0.208632 | 0.051* | |
C13 | 0.2669 (4) | 0.6990 (3) | 0.1967 (3) | 0.0406 (11) | |
H13 | 0.248927 | 0.769140 | 0.203727 | 0.049* | |
C14 | 0.3735 (3) | 0.6705 (3) | 0.1836 (3) | 0.0345 (10) | |
H14 | 0.428998 | 0.720940 | 0.181615 | 0.041* | |
C15 | 0.4870 (3) | 0.6581 (3) | −0.1938 (3) | 0.0322 (9) | |
C16 | 0.5569 (4) | 0.5795 (3) | −0.2208 (3) | 0.0391 (10) | |
H16 | 0.585269 | 0.533863 | −0.174979 | 0.047* | |
C17 | 0.5849 (4) | 0.5681 (4) | −0.3153 (3) | 0.0514 (13) | |
H17 | 0.633985 | 0.515797 | −0.333780 | 0.062* | |
C18 | 0.5419 (4) | 0.6322 (4) | −0.3812 (3) | 0.0547 (14) | |
H18 | 0.559414 | 0.622751 | −0.445721 | 0.066* | |
C19 | 0.4738 (4) | 0.7098 (4) | −0.3555 (3) | 0.0481 (12) | |
H19 | 0.445533 | 0.754590 | −0.402084 | 0.058* | |
C20 | 0.4456 (4) | 0.7235 (3) | −0.2617 (3) | 0.0396 (10) | |
H20 | 0.398261 | 0.777529 | −0.244058 | 0.047* | |
C21 | 0.3463 (3) | 0.5701 (3) | −0.0566 (3) | 0.0302 (9) | |
C22 | 0.3761 (4) | 0.4679 (3) | −0.0612 (3) | 0.0359 (10) | |
H22 | 0.450739 | 0.449838 | −0.063759 | 0.043* | |
C23 | 0.2974 (4) | 0.3922 (3) | −0.0619 (3) | 0.0422 (11) | |
H23 | 0.318214 | 0.322403 | −0.064286 | 0.051* | |
C24 | 0.1897 (4) | 0.4180 (4) | −0.0592 (3) | 0.0486 (13) | |
H24 | 0.135887 | 0.366066 | −0.060870 | 0.058* | |
C25 | 0.1589 (4) | 0.5196 (4) | −0.0539 (3) | 0.0493 (13) | |
H25 | 0.084124 | 0.537013 | −0.051412 | 0.059* | |
C26 | 0.2363 (3) | 0.5953 (3) | −0.0524 (3) | 0.0384 (10) | |
H26 | 0.214848 | 0.664858 | −0.048423 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0477 (7) | 0.0281 (5) | 0.0503 (6) | 0.0058 (5) | 0.0037 (6) | −0.0026 (5) |
S2 | 0.0449 (7) | 0.0288 (6) | 0.0457 (6) | 0.0060 (5) | −0.0003 (5) | −0.0047 (5) |
P1 | 0.0292 (6) | 0.0273 (5) | 0.0335 (6) | 0.0022 (5) | 0.0029 (5) | 0.0011 (4) |
P2 | 0.0285 (5) | 0.0265 (5) | 0.0293 (5) | 0.0007 (5) | 0.0001 (5) | −0.0009 (4) |
C1 | 0.023 (2) | 0.037 (2) | 0.032 (2) | −0.0012 (18) | 0.0015 (17) | −0.0013 (18) |
C2 | 0.026 (2) | 0.030 (2) | 0.032 (2) | −0.0026 (17) | 0.0026 (17) | −0.0007 (17) |
C3 | 0.025 (2) | 0.033 (2) | 0.032 (2) | 0.0029 (18) | 0.0009 (18) | 0.0031 (18) |
C4 | 0.051 (3) | 0.034 (2) | 0.039 (2) | 0.005 (2) | −0.012 (2) | 0.007 (2) |
C5 | 0.055 (3) | 0.039 (3) | 0.050 (3) | 0.001 (2) | −0.014 (2) | −0.001 (2) |
C6 | 0.033 (2) | 0.054 (3) | 0.032 (2) | 0.003 (2) | −0.0022 (19) | 0.001 (2) |
C7 | 0.035 (2) | 0.054 (3) | 0.045 (3) | 0.005 (2) | −0.003 (2) | 0.020 (2) |
C8 | 0.036 (2) | 0.036 (2) | 0.043 (3) | 0.004 (2) | 0.001 (2) | 0.008 (2) |
C9 | 0.027 (2) | 0.033 (2) | 0.026 (2) | −0.0001 (18) | 0.0009 (17) | 0.0013 (17) |
C10 | 0.037 (2) | 0.032 (2) | 0.038 (2) | −0.002 (2) | 0.0031 (19) | 0.0012 (19) |
C11 | 0.033 (2) | 0.044 (3) | 0.043 (2) | −0.010 (2) | 0.006 (2) | 0.001 (2) |
C12 | 0.026 (2) | 0.058 (3) | 0.042 (3) | 0.007 (2) | 0.0074 (19) | −0.001 (2) |
C13 | 0.041 (3) | 0.035 (3) | 0.046 (3) | 0.008 (2) | 0.004 (2) | −0.003 (2) |
C14 | 0.032 (2) | 0.030 (2) | 0.041 (2) | −0.0025 (19) | 0.0039 (19) | −0.0013 (19) |
C15 | 0.030 (2) | 0.032 (2) | 0.034 (2) | −0.0089 (18) | 0.0019 (17) | −0.0035 (18) |
C16 | 0.032 (2) | 0.047 (3) | 0.038 (2) | −0.004 (2) | −0.001 (2) | −0.0075 (19) |
C17 | 0.034 (3) | 0.074 (4) | 0.047 (3) | −0.003 (2) | 0.008 (2) | −0.021 (3) |
C18 | 0.044 (3) | 0.087 (4) | 0.033 (2) | −0.020 (3) | 0.007 (2) | −0.010 (3) |
C19 | 0.048 (3) | 0.064 (3) | 0.032 (2) | −0.017 (3) | −0.003 (2) | 0.009 (2) |
C20 | 0.040 (3) | 0.041 (3) | 0.038 (2) | −0.008 (2) | 0.001 (2) | 0.0036 (19) |
C21 | 0.032 (2) | 0.034 (2) | 0.025 (2) | −0.0023 (18) | 0.0013 (17) | −0.0023 (18) |
C22 | 0.039 (2) | 0.035 (2) | 0.033 (2) | 0.000 (2) | 0.0060 (19) | −0.0055 (19) |
C23 | 0.051 (3) | 0.037 (3) | 0.038 (3) | −0.012 (2) | 0.008 (2) | −0.004 (2) |
C24 | 0.052 (3) | 0.056 (3) | 0.038 (3) | −0.026 (3) | 0.006 (2) | −0.006 (2) |
C25 | 0.032 (2) | 0.068 (3) | 0.048 (3) | −0.011 (2) | 0.005 (2) | 0.000 (3) |
C26 | 0.032 (2) | 0.046 (3) | 0.038 (2) | 0.002 (2) | 0.0012 (19) | 0.000 (2) |
S1—P1 | 1.9571 (15) | C12—H12 | 0.9500 |
S2—P2 | 1.9529 (15) | C12—C13 | 1.376 (6) |
P1—C1 | 1.804 (4) | C13—H13 | 0.9500 |
P1—C3 | 1.824 (4) | C13—C14 | 1.378 (6) |
P1—C9 | 1.812 (4) | C14—H14 | 0.9500 |
P2—C2 | 1.808 (4) | C15—C16 | 1.396 (6) |
P2—C15 | 1.819 (4) | C15—C20 | 1.387 (6) |
P2—C21 | 1.810 (4) | C16—H16 | 0.9500 |
C1—H1 | 0.9500 | C16—C17 | 1.395 (6) |
C1—C2 | 1.338 (5) | C17—H17 | 0.9500 |
C2—H2 | 0.9500 | C17—C18 | 1.365 (7) |
C3—C4 | 1.384 (6) | C18—H18 | 0.9500 |
C3—C8 | 1.389 (6) | C18—C19 | 1.367 (7) |
C4—H4 | 0.9500 | C19—H19 | 0.9500 |
C4—C5 | 1.386 (6) | C19—C20 | 1.390 (6) |
C5—H5 | 0.9500 | C20—H20 | 0.9500 |
C5—C6 | 1.375 (6) | C21—C22 | 1.389 (6) |
C6—H6 | 0.9500 | C21—C26 | 1.395 (6) |
C6—C7 | 1.372 (6) | C22—H22 | 0.9500 |
C7—H7 | 0.9500 | C22—C23 | 1.386 (6) |
C7—C8 | 1.383 (6) | C23—H23 | 0.9500 |
C8—H8 | 0.9500 | C23—C24 | 1.369 (7) |
C9—C10 | 1.387 (6) | C24—H24 | 0.9500 |
C9—C14 | 1.387 (5) | C24—C25 | 1.384 (7) |
C10—H10 | 0.9500 | C25—H25 | 0.9500 |
C10—C11 | 1.380 (6) | C25—C26 | 1.375 (6) |
C11—H11 | 0.9500 | C26—H26 | 0.9500 |
C11—C12 | 1.387 (6) | ||
C1—P1—S1 | 111.69 (14) | C11—C12—H12 | 119.8 |
C1—P1—C3 | 101.08 (18) | C13—C12—C11 | 120.4 (4) |
C1—P1—C9 | 109.73 (18) | C13—C12—H12 | 119.8 |
C3—P1—S1 | 112.42 (14) | C12—C13—H13 | 119.8 |
C9—P1—S1 | 114.89 (14) | C12—C13—C14 | 120.3 (4) |
C9—P1—C3 | 106.02 (18) | C14—C13—H13 | 119.8 |
C2—P2—S2 | 109.54 (13) | C9—C14—H14 | 120.1 |
C2—P2—C15 | 100.75 (18) | C13—C14—C9 | 119.8 (4) |
C2—P2—C21 | 113.85 (18) | C13—C14—H14 | 120.1 |
C15—P2—S2 | 112.62 (14) | C16—C15—P2 | 120.8 (3) |
C21—P2—S2 | 115.48 (14) | C20—C15—P2 | 119.7 (3) |
C21—P2—C15 | 103.53 (18) | C20—C15—C16 | 119.4 (4) |
P1—C1—H1 | 112.4 | C15—C16—H16 | 120.1 |
C2—C1—P1 | 135.2 (3) | C17—C16—C15 | 119.8 (4) |
C2—C1—H1 | 112.4 | C17—C16—H16 | 120.1 |
P2—C2—H2 | 111.6 | C16—C17—H17 | 120.0 |
C1—C2—P2 | 136.7 (3) | C18—C17—C16 | 119.9 (5) |
C1—C2—H2 | 111.6 | C18—C17—H17 | 120.0 |
C4—C3—P1 | 121.8 (3) | C17—C18—H18 | 119.6 |
C4—C3—C8 | 119.2 (4) | C17—C18—C19 | 120.8 (4) |
C8—C3—P1 | 119.0 (3) | C19—C18—H18 | 119.6 |
C3—C4—H4 | 120.0 | C18—C19—H19 | 119.8 |
C3—C4—C5 | 120.1 (4) | C18—C19—C20 | 120.4 (4) |
C5—C4—H4 | 120.0 | C20—C19—H19 | 119.8 |
C4—C5—H5 | 119.7 | C15—C20—C19 | 119.7 (4) |
C6—C5—C4 | 120.6 (5) | C15—C20—H20 | 120.1 |
C6—C5—H5 | 119.7 | C19—C20—H20 | 120.1 |
C5—C6—H6 | 120.3 | C22—C21—P2 | 121.7 (3) |
C7—C6—C5 | 119.3 (4) | C22—C21—C26 | 119.1 (4) |
C7—C6—H6 | 120.3 | C26—C21—P2 | 118.7 (3) |
C6—C7—H7 | 119.5 | C21—C22—H22 | 119.9 |
C6—C7—C8 | 121.0 (4) | C23—C22—C21 | 120.3 (4) |
C8—C7—H7 | 119.5 | C23—C22—H22 | 119.9 |
C3—C8—H8 | 120.1 | C22—C23—H23 | 120.0 |
C7—C8—C3 | 119.8 (4) | C24—C23—C22 | 120.0 (4) |
C7—C8—H8 | 120.1 | C24—C23—H23 | 120.0 |
C10—C9—P1 | 118.9 (3) | C23—C24—H24 | 119.9 |
C10—C9—C14 | 119.7 (4) | C23—C24—C25 | 120.2 (4) |
C14—C9—P1 | 121.4 (3) | C25—C24—H24 | 119.9 |
C9—C10—H10 | 119.8 | C24—C25—H25 | 119.9 |
C11—C10—C9 | 120.4 (4) | C26—C25—C24 | 120.2 (4) |
C11—C10—H10 | 119.8 | C26—C25—H25 | 119.9 |
C10—C11—H11 | 120.3 | C21—C26—H26 | 119.9 |
C10—C11—C12 | 119.4 (4) | C25—C26—C21 | 120.1 (4) |
C12—C11—H11 | 120.3 | C25—C26—H26 | 119.9 |
S1—P1—C1—C2 | 92.9 (4) | C4—C5—C6—C7 | −1.2 (7) |
S1—P1—C3—C4 | 158.3 (3) | C5—C6—C7—C8 | 1.0 (7) |
S1—P1—C3—C8 | −21.4 (4) | C6—C7—C8—C3 | 0.2 (7) |
S1—P1—C9—C10 | 7.6 (4) | C8—C3—C4—C5 | 1.0 (7) |
S1—P1—C9—C14 | −173.9 (3) | C9—P1—C1—C2 | −35.7 (5) |
S2—P2—C2—C1 | 96.9 (4) | C9—P1—C3—C4 | −75.4 (4) |
S2—P2—C15—C16 | 159.7 (3) | C9—P1—C3—C8 | 104.9 (3) |
S2—P2—C15—C20 | −23.4 (4) | C9—C10—C11—C12 | −1.3 (6) |
S2—P2—C21—C22 | −170.6 (3) | C10—C9—C14—C13 | −0.8 (6) |
S2—P2—C21—C26 | 17.8 (4) | C10—C11—C12—C13 | 0.5 (7) |
P1—C1—C2—P2 | 9.2 (7) | C11—C12—C13—C14 | 0.1 (7) |
P1—C3—C4—C5 | −178.6 (4) | C12—C13—C14—C9 | 0.1 (6) |
P1—C3—C8—C7 | 178.4 (3) | C14—C9—C10—C11 | 1.4 (6) |
P1—C9—C10—C11 | −180.0 (3) | C15—P2—C2—C1 | −144.2 (4) |
P1—C9—C14—C13 | −179.4 (3) | C15—P2—C21—C22 | 65.9 (4) |
P2—C15—C16—C17 | 177.4 (3) | C15—P2—C21—C26 | −105.8 (3) |
P2—C15—C20—C19 | −176.7 (3) | C15—C16—C17—C18 | −1.7 (7) |
P2—C21—C22—C23 | −171.3 (3) | C16—C15—C20—C19 | 0.3 (6) |
P2—C21—C26—C25 | 171.0 (3) | C16—C17—C18—C19 | 2.0 (7) |
C1—P1—C3—C4 | 39.0 (4) | C17—C18—C19—C20 | −1.2 (7) |
C1—P1—C3—C8 | −140.6 (3) | C18—C19—C20—C15 | 0.0 (7) |
C1—P1—C9—C10 | 134.4 (3) | C20—C15—C16—C17 | 0.5 (6) |
C1—P1—C9—C14 | −47.1 (4) | C21—P2—C2—C1 | −34.1 (5) |
C2—P2—C15—C16 | 43.0 (4) | C21—P2—C15—C16 | −74.9 (4) |
C2—P2—C15—C20 | −140.0 (3) | C21—P2—C15—C20 | 102.0 (3) |
C2—P2—C21—C22 | −42.5 (4) | C21—C22—C23—C24 | 0.7 (6) |
C2—P2—C21—C26 | 145.8 (3) | C22—C21—C26—C25 | −0.8 (6) |
C3—P1—C1—C2 | −147.3 (4) | C22—C23—C24—C25 | −1.2 (7) |
C3—P1—C9—C10 | −117.2 (3) | C23—C24—C25—C26 | 0.6 (7) |
C3—P1—C9—C14 | 61.3 (4) | C24—C25—C26—C21 | 0.4 (7) |
C3—C4—C5—C6 | 0.2 (7) | C26—C21—C22—C23 | 0.3 (6) |
C4—C3—C8—C7 | −1.2 (6) |
Cg is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···S2i | 0.95 | 2.86 | 3.742 (4) | 155 |
C7—H7···S2ii | 0.95 | 2.82 | 3.561 (5) | 135 |
C8—H8···S1 | 0.95 | 2.86 | 3.344 (4) | 113 |
C10—H10···S1 | 0.95 | 2.84 | 3.360 (4) | 116 |
C20—H20···S2 | 0.95 | 2.89 | 3.367 (4) | 113 |
C26—H26···S2 | 0.95 | 2.89 | 3.394 (4) | 115 |
C11—H11···Cgiii | 0.95 | 2.63 | 3.573 (5) | 171 |
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1/2, −y+1, z+1/2. |
[PtCl2(C26H22P2S2)] | Dx = 1.890 Mg m−3 |
Mr = 726.48 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fdd2 | Cell parameters from 9927 reflections |
a = 18.0724 (12) Å | θ = 2.5–25.4° |
b = 30.163 (2) Å | µ = 6.01 mm−1 |
c = 9.3697 (6) Å | T = 173 K |
V = 5107.5 (6) Å3 | Plate, yellow |
Z = 8 | 0.35 × 0.14 × 0.10 mm |
F(000) = 2816 |
Bruker APEXII CCD diffractometer | 2324 independent reflections |
Radiation source: sealed tube | 2227 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 8 pixels mm-1 | θmax = 25.4°, θmin = 2.5° |
φ and ω scans | h = −21→21 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −36→36 |
Tmin = 0.543, Tmax = 0.745 | l = −11→11 |
20596 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.0372P)2 + 4.1023P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.061 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 1.82 e Å−3 |
2324 reflections | Δρmin = −0.47 e Å−3 |
150 parameters | Absolute structure: Flack x determined using 1010 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al. 2013) |
1 restraint | Absolute structure parameter: −0.006 (4) |
Primary atom site location: heavy-atom method |
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. |
x | y | z | Uiso*/Ueq | ||
Pt1 | 0.500000 | 0.500000 | −0.21568 (8) | 0.02096 (13) | |
S1 | 0.44478 (10) | 0.54577 (6) | −0.0554 (2) | 0.0278 (4) | |
Cl1 | 0.55528 (10) | 0.45658 (6) | −0.3904 (2) | 0.0322 (4) | |
P1 | 0.51249 (11) | 0.55887 (7) | 0.1097 (2) | 0.0232 (4) | |
C1 | 0.5064 (5) | 0.5214 (3) | 0.2610 (10) | 0.027 (2) | |
H1 | 0.513340 | 0.534545 | 0.352168 | 0.032* | |
C6 | 0.3769 (4) | 0.6526 (3) | 0.2775 (10) | 0.0340 (16) | |
H6 | 0.326369 | 0.654598 | 0.304722 | 0.041* | |
C4 | 0.4948 (5) | 0.6864 (3) | 0.2493 (10) | 0.037 (3) | |
H4 | 0.525799 | 0.711707 | 0.258970 | 0.045* | |
C5 | 0.4219 (5) | 0.6890 (3) | 0.2897 (11) | 0.0378 (18) | |
H5 | 0.402617 | 0.715993 | 0.326227 | 0.045* | |
C3 | 0.5238 (5) | 0.6471 (3) | 0.1941 (10) | 0.0334 (18) | |
H3 | 0.573993 | 0.645788 | 0.164031 | 0.040* | |
C2 | 0.4790 (4) | 0.6101 (3) | 0.1836 (8) | 0.0272 (16) | |
C7 | 0.4047 (5) | 0.6130 (3) | 0.2256 (8) | 0.0340 (18) | |
H7 | 0.373423 | 0.587756 | 0.218478 | 0.041* | |
C8 | 0.6089 (4) | 0.5641 (2) | 0.0639 (8) | 0.0263 (17) | |
C13 | 0.6637 (4) | 0.5485 (3) | 0.1545 (9) | 0.0332 (18) | |
H13 | 0.650228 | 0.534949 | 0.242200 | 0.040* | |
C9 | 0.6287 (4) | 0.5837 (3) | −0.0631 (9) | 0.0358 (19) | |
H9 | 0.591769 | 0.594278 | −0.126754 | 0.043* | |
C12 | 0.7374 (5) | 0.5524 (3) | 0.1194 (12) | 0.037 (2) | |
H12 | 0.774484 | 0.541843 | 0.182621 | 0.044* | |
C11 | 0.7569 (5) | 0.5718 (3) | −0.0084 (11) | 0.035 (3) | |
H11 | 0.807545 | 0.574026 | −0.034541 | 0.043* | |
C10 | 0.7034 (5) | 0.5880 (3) | −0.0977 (11) | 0.047 (2) | |
H10 | 0.717297 | 0.602202 | −0.184109 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt1 | 0.01883 (18) | 0.02136 (18) | 0.02268 (19) | 0.0004 (3) | 0.000 | 0.000 |
S1 | 0.0218 (10) | 0.0335 (11) | 0.0283 (10) | 0.0078 (8) | −0.0036 (8) | −0.0072 (8) |
Cl1 | 0.0339 (10) | 0.0340 (10) | 0.0287 (11) | 0.0051 (8) | 0.0031 (9) | −0.0066 (8) |
P1 | 0.0256 (9) | 0.0202 (9) | 0.0238 (10) | −0.0008 (7) | 0.0003 (8) | −0.0017 (8) |
C1 | 0.020 (4) | 0.045 (4) | 0.015 (6) | 0.004 (4) | −0.004 (3) | −0.012 (4) |
C6 | 0.024 (4) | 0.041 (4) | 0.036 (4) | 0.006 (3) | 0.004 (4) | −0.002 (4) |
C4 | 0.037 (5) | 0.023 (4) | 0.052 (9) | −0.002 (4) | 0.004 (5) | −0.007 (4) |
C5 | 0.036 (4) | 0.032 (4) | 0.046 (5) | 0.009 (3) | 0.000 (4) | −0.008 (4) |
C3 | 0.024 (4) | 0.028 (4) | 0.047 (5) | −0.001 (3) | −0.002 (4) | −0.007 (4) |
C2 | 0.030 (4) | 0.024 (4) | 0.028 (4) | 0.001 (3) | −0.003 (3) | −0.002 (3) |
C7 | 0.031 (5) | 0.036 (4) | 0.035 (4) | −0.004 (4) | 0.006 (3) | −0.003 (3) |
C8 | 0.022 (4) | 0.020 (3) | 0.037 (5) | −0.002 (3) | −0.002 (3) | −0.008 (3) |
C13 | 0.027 (4) | 0.036 (4) | 0.037 (5) | 0.002 (3) | −0.002 (3) | −0.002 (3) |
C9 | 0.026 (4) | 0.039 (5) | 0.042 (5) | 0.002 (3) | −0.004 (4) | 0.005 (4) |
C12 | 0.028 (4) | 0.037 (5) | 0.045 (6) | 0.004 (4) | −0.004 (4) | −0.005 (5) |
C11 | 0.023 (5) | 0.033 (5) | 0.051 (8) | −0.005 (4) | 0.006 (4) | −0.007 (4) |
C10 | 0.040 (5) | 0.053 (6) | 0.049 (6) | −0.011 (4) | 0.009 (4) | 0.006 (4) |
Pt1—S1 | 2.2712 (19) | C5—H5 | 0.9500 |
Pt1—S1i | 2.2712 (19) | C3—H3 | 0.9500 |
Pt1—Cl1 | 2.3226 (19) | C3—C2 | 1.382 (12) |
Pt1—Cl1i | 2.3226 (19) | C2—C7 | 1.403 (11) |
S1—P1 | 2.012 (3) | C7—H7 | 0.9500 |
P1—C1 | 1.816 (9) | C8—C13 | 1.387 (11) |
P1—C2 | 1.799 (8) | C8—C9 | 1.377 (11) |
P1—C8 | 1.801 (7) | C13—H13 | 0.9500 |
C1—C1i | 1.312 (18) | C13—C12 | 1.377 (12) |
C1—H1 | 0.9500 | C9—H9 | 0.9500 |
C6—H6 | 0.9500 | C9—C10 | 1.394 (12) |
C6—C5 | 1.370 (11) | C12—H12 | 0.9500 |
C6—C7 | 1.384 (11) | C12—C11 | 1.379 (14) |
C4—H4 | 0.9500 | C11—H11 | 0.9500 |
C4—C5 | 1.373 (13) | C11—C10 | 1.367 (14) |
C4—C3 | 1.397 (12) | C10—H10 | 0.9500 |
S1—Pt1—S1i | 97.19 (10) | C2—C3—C4 | 119.5 (8) |
S1i—Pt1—Cl1 | 86.24 (6) | C2—C3—H3 | 120.3 |
S1i—Pt1—Cl1i | 176.41 (8) | C3—C2—P1 | 121.6 (6) |
S1—Pt1—Cl1 | 176.41 (8) | C3—C2—C7 | 119.5 (7) |
S1—Pt1—Cl1i | 86.24 (6) | C7—C2—P1 | 118.9 (6) |
Cl1—Pt1—Cl1i | 90.34 (10) | C6—C7—C2 | 119.9 (7) |
P1—S1—Pt1 | 111.14 (10) | C6—C7—H7 | 120.0 |
C1—P1—S1 | 116.2 (3) | C2—C7—H7 | 120.0 |
C2—P1—S1 | 105.1 (3) | C13—C8—P1 | 121.0 (6) |
C2—P1—C1 | 102.4 (4) | C9—C8—P1 | 119.7 (6) |
C2—P1—C8 | 110.0 (4) | C9—C8—C13 | 119.2 (7) |
C8—P1—S1 | 115.0 (3) | C8—C13—H13 | 119.5 |
C8—P1—C1 | 107.4 (4) | C12—C13—C8 | 121.1 (8) |
P1—C1—H1 | 115.7 | C12—C13—H13 | 119.5 |
C1i—C1—P1 | 128.6 (3) | C8—C9—H9 | 120.2 |
C1i—C1—H1 | 115.7 | C8—C9—C10 | 119.5 (8) |
C5—C6—H6 | 119.8 | C10—C9—H9 | 120.2 |
C5—C6—C7 | 120.3 (7) | C13—C12—H12 | 120.3 |
C7—C6—H6 | 119.8 | C13—C12—C11 | 119.4 (9) |
C5—C4—H4 | 119.7 | C11—C12—H12 | 120.3 |
C5—C4—C3 | 120.7 (8) | C12—C11—H11 | 119.9 |
C3—C4—H4 | 119.7 | C10—C11—C12 | 120.1 (8) |
C6—C5—C4 | 120.1 (7) | C10—C11—H11 | 119.9 |
C6—C5—H5 | 119.9 | C9—C10—H10 | 119.7 |
C4—C5—H5 | 119.9 | C11—C10—C9 | 120.6 (9) |
C4—C3—H3 | 120.3 | C11—C10—H10 | 119.7 |
S1—P1—C1—C1i | 35.0 (13) | C3—C4—C5—C6 | 0.6 (15) |
S1—P1—C2—C3 | −121.8 (7) | C3—C2—C7—C6 | −0.2 (12) |
S1—P1—C2—C7 | 55.4 (7) | C2—P1—C1—C1i | 148.8 (11) |
S1—P1—C8—C13 | −143.1 (5) | C2—P1—C8—C13 | 98.5 (7) |
S1—P1—C8—C9 | 36.7 (7) | C2—P1—C8—C9 | −81.6 (7) |
P1—C2—C7—C6 | −177.5 (7) | C7—C6—C5—C4 | 0.6 (14) |
P1—C8—C13—C12 | 179.9 (7) | C8—P1—C1—C1i | −95.3 (12) |
P1—C8—C9—C10 | 179.5 (7) | C8—P1—C2—C3 | 2.4 (8) |
C1—P1—C2—C3 | 116.4 (7) | C8—P1—C2—C7 | 179.7 (6) |
C1—P1—C2—C7 | −66.4 (7) | C8—C13—C12—C11 | −0.5 (13) |
C1—P1—C8—C13 | −12.1 (7) | C8—C9—C10—C11 | 1.7 (14) |
C1—P1—C8—C9 | 167.7 (6) | C13—C8—C9—C10 | −0.6 (12) |
C4—C3—C2—P1 | 178.6 (7) | C13—C12—C11—C10 | 1.5 (13) |
C4—C3—C2—C7 | 1.4 (13) | C9—C8—C13—C12 | 0.0 (12) |
C5—C6—C7—C2 | −0.8 (13) | C12—C11—C10—C9 | −2.1 (14) |
C5—C4—C3—C2 | −1.6 (14) |
Symmetry code: (i) −x+1, −y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···Cl1ii | 0.95 | 2.73 | 3.515 (10) | 141 |
C3—H3···S1iii | 0.95 | 2.82 | 3.538 (9) | 133 |
Symmetry codes: (ii) −x+1, −y+1, z+1; (iii) x+1/4, −y+5/4, z+1/4. |
Acknowledgements
We thank GVSU for funding (Chemistry Department Weldon Fund, CSCE, Library Open Access Fund), and Pfizer, Inc. for the donation of a Varian INOVA 400 FT NMR. The CCD-based X-ray diffractometers at Michigan State University were upgraded and/or replaced by departmental funds.
Funding information
Funding for this research was provided by: GVSU CSCE (Research Grant-in-aid to B. Rawls).
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