metal-organic compounds
Bis(μ-diethyl sulfide-κ2S:S)bis[(biphenyl-2,2′-diyl)platinum(ll)]
aDepartment of Chemistry, Wichita State University, Wichita, KS 67260, USA, and bCrystallographic Laboratory, University of California, San Diego, La Jolla, CA 92093, USA
*Correspondence e-mail: paul.rillema@wichita.edu
The C4S2 donor set in the title compound, [Pt(C12H8){(C2H5)2S}]2, defines a distorted square-planar geometry about the two PtII atoms, with very small deviations from planarity. The bidentate nature of the biphenyl dianionic ligand results in C—Pt—C bond angles of 80.9 (2) and 81.2 (2)°; the S—Pt—S bond angles are 78.08 (5) and 78.09 (5)°. The average Pt—C bond length is 2.023 Å [range 2.016 (5)–2.028 (6) Å] and the average of Pt—S bond length is 2.3790 Å [range 2.3742 (14)–2.3837 (14) Å].
CCDC reference: 1479776
Structure description
We are interested in preparing PtII complexes containing the biphenyl dianion with diimine ligands due to their emission properties (Rillema et al., 2015). [Pt(C12H8){(C2H5)2S}]2 (Fig. 1) is a synthetic intermediate. The bidentate nature of the 2,2′-biphenyl ligand gave C—Pt—C bite angles of 80.9 (2) and 81.2 (2)°, as expected from previous studies (Rillema et al., 2013), but the S—Pt—S angles of 78.08 (5) and 78.09 (5)° for the square-planar biphenyl–PtII units bridged by sulfur ligands was ∼2° less than what had been found for a similar diethyl sulfide-bridged platinum(II) complex with four 4-fluorophenyl groups in place of the two bidentate biphenyl ligands (Escola et al., 2014). Substitution of the bridging sulfur ligands with Br gave Br—Pt—Br angles of 83.0 (1)° and Pt—C bond lengths of 2.01 (2) and 2.01 (2) Å for the bis{(μ2-bromido)[(2,2′-η2)-4,4′-bis(trifluoromethyl)biphenyl]platinum(II)} anion (Brune et al., 1991).
Synthesis and crystallization
The title compound was synthesized according to previously published procedures (Gilman & Gaj, 1957; Gardner et al., 1973). X-ray quality crystals were obtained by recrystallization from benzene.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1479776
10.1107/S2414314616007896/zl4008sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616007896/zl4008Isup2.hkl
The title compound was synthesized according to previously published procedures (Gilman & Gaj, 1957; Gardner et al., 1973). X-ray quality crystals were obtained by recrystallization from benzene.
Crystal data, data collection and structure
details are summarized in Table 1. H atoms attached to C atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H bond lengths of 0.95 Å for aromatic C—H, and 0.99 and 0.98 Å for aliphatic CH2 and CH3 moieties, respectively. Methyl H atoms were allowed to rotate but not to tip to best fit the experimental electron density. Uiso(H) values were set to a multiple of Ueq(C) with 1.5 for CH3 and 1.2 for C—H and CH2 units, respectively.We are interested in preparing PtII complexes containing the biphenyl dianion with diimine ligands due to their ~2° less than what had been found for a similarly diethyl sulfide-bridged platinum(II) complex with four 4-fluorophenyl groups in place of the two bidentate biphenyl ligands (Escola et al., 2014). Substitution of the bridging sulfur ligands with Br gave Br—Pt—Br angles of 83.0 (1)° and Pt—C bond lenghts of 2.01 (2) and 2.01 (2) Å for the bis{(µ2-bromo)2,2'-η2-[4,4'-bis(trifluoromethyl)biphenyl]platinum(II)} anion (Brune et al., 1991).
emission properties (Rillema et al., 2015). [Pt(C12H10)((C2H5)2S)]2 is a synthetic intermediate. The bidentate nature of the 2,2'-biphenyl ligand gave C—Pt—C bite angles of 81.9 (2) and 81.2 (2)°, as expected from previous studies (Rillema et al., 2013), but the S—Pt—S angles of 78.08 (5) and 78.09 (5)° for the square-planar biphenyl–PtII units bridged by sulfur ligands wasData collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. H atoms have been omitted for clarity. |
[Pt2(C12H10)2(C4H8S)2] | F(000) = 1664 |
Mr = 874.91 | Dx = 2.059 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 19.2938 (15) Å | Cell parameters from 9904 reflections |
b = 7.8839 (6) Å | θ = 2.2–28.3° |
c = 19.6969 (17) Å | µ = 10.07 mm−1 |
β = 109.639 (5)° | T = 100 K |
V = 2821.8 (4) Å3 | Rod, yellow |
Z = 4 | 0.05 × 0.02 × 0.01 mm |
Bruker APEXII Ultra diffractometer | 6763 independent reflections |
Radiation source: Micro Focus Rotating Anode, Bruker TXS | 5668 reflections with I > 2σ(I) |
Double Bounce Multilayer Mirrors monochromator | Rint = 0.052 |
Detector resolution: 7.9 pixels mm-1 | θmax = 28.3°, θmin = 2.8° |
ω and φ scans | h = −23→25 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −10→10 |
Tmin = 0.018, Tmax = 0.048 | l = −26→26 |
39433 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0141P)2 + 15.5401P] where P = (Fo2 + 2Fc2)/3 |
6763 reflections | (Δ/σ)max = 0.001 |
329 parameters | Δρmax = 1.93 e Å−3 |
0 restraints | Δρmin = −1.80 e Å−3 |
[Pt2(C12H10)2(C4H8S)2] | V = 2821.8 (4) Å3 |
Mr = 874.91 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 19.2938 (15) Å | µ = 10.07 mm−1 |
b = 7.8839 (6) Å | T = 100 K |
c = 19.6969 (17) Å | 0.05 × 0.02 × 0.01 mm |
β = 109.639 (5)° |
Bruker APEXII Ultra diffractometer | 6763 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | 5668 reflections with I > 2σ(I) |
Tmin = 0.018, Tmax = 0.048 | Rint = 0.052 |
39433 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0141P)2 + 15.5401P] where P = (Fo2 + 2Fc2)/3 |
6763 reflections | Δρmax = 1.93 e Å−3 |
329 parameters | Δρmin = −1.80 e Å−3 |
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 | 1.06321 (2) | 0.28426 (3) | 0.22858 (2) | 0.01920 (6) | |
Pt2 | 0.92032 (2) | 0.59665 (3) | 0.22827 (2) | 0.01973 (6) | |
S1 | 0.96358 (8) | 0.43818 (17) | 0.14799 (7) | 0.0201 (3) | |
S2 | 1.02012 (8) | 0.44260 (17) | 0.30952 (7) | 0.0209 (3) | |
C1 | 1.1019 (3) | 0.1619 (7) | 0.1581 (3) | 0.0205 (11) | |
C2 | 1.1493 (3) | 0.1631 (7) | 0.2996 (3) | 0.0198 (11) | |
C3 | 0.8333 (3) | 0.7156 (7) | 0.1570 (3) | 0.0216 (12) | |
C4 | 0.8827 (3) | 0.7209 (7) | 0.2990 (3) | 0.0210 (11) | |
C5 | 1.0705 (3) | 0.1585 (7) | 0.0830 (3) | 0.0230 (12) | |
H5 | 1.0250 | 0.2150 | 0.0607 | 0.028* | |
C6 | 1.1040 (3) | 0.0741 (7) | 0.0399 (3) | 0.0234 (12) | |
H6 | 1.0818 | 0.0746 | −0.0110 | 0.028* | |
C7 | 1.1697 (3) | −0.0101 (7) | 0.0720 (3) | 0.0250 (13) | |
H7 | 1.1932 | −0.0667 | 0.0431 | 0.030* | |
C8 | 1.2013 (3) | −0.0117 (7) | 0.1466 (3) | 0.0248 (12) | |
H8 | 1.2462 | −0.0708 | 0.1686 | 0.030* | |
C9 | 1.1680 (3) | 0.0720 (7) | 0.1893 (3) | 0.0204 (11) | |
C10 | 1.1955 (3) | 0.0738 (7) | 0.2690 (3) | 0.0207 (12) | |
C11 | 1.2586 (3) | −0.0065 (7) | 0.3120 (3) | 0.0244 (12) | |
H11 | 1.2890 | −0.0643 | 0.2903 | 0.029* | |
C12 | 1.2781 (3) | −0.0034 (7) | 0.3867 (3) | 0.0263 (13) | |
H12 | 1.3220 | −0.0568 | 0.4163 | 0.032* | |
C13 | 1.2327 (3) | 0.0781 (7) | 0.4172 (3) | 0.0264 (13) | |
H13 | 1.2445 | 0.0776 | 0.4681 | 0.032* | |
C14 | 1.1696 (3) | 0.1612 (7) | 0.3741 (3) | 0.0249 (12) | |
H14 | 1.1395 | 0.2182 | 0.3964 | 0.030* | |
C15 | 0.8112 (3) | 0.7139 (7) | 0.0820 (3) | 0.0227 (12) | |
H15 | 0.8405 | 0.6553 | 0.0593 | 0.027* | |
C16 | 0.7473 (3) | 0.7956 (7) | 0.0391 (3) | 0.0241 (12) | |
H16 | 0.7338 | 0.7915 | −0.0120 | 0.029* | |
C17 | 0.7035 (3) | 0.8824 (7) | 0.0704 (3) | 0.0259 (13) | |
H17 | 0.6594 | 0.9356 | 0.0412 | 0.031* | |
C18 | 0.7250 (3) | 0.8909 (7) | 0.1456 (3) | 0.0257 (13) | |
H18 | 0.6963 | 0.9538 | 0.1676 | 0.031* | |
C19 | 0.7881 (3) | 0.8078 (7) | 0.1883 (3) | 0.0221 (12) | |
C20 | 0.8163 (3) | 0.8089 (7) | 0.2682 (3) | 0.0231 (12) | |
C21 | 0.7823 (3) | 0.8892 (7) | 0.3106 (3) | 0.0259 (13) | |
H21 | 0.7366 | 0.9452 | 0.2885 | 0.031* | |
C22 | 0.8140 (3) | 0.8894 (8) | 0.3854 (3) | 0.0280 (13) | |
H22 | 0.7900 | 0.9433 | 0.4146 | 0.034* | |
C23 | 0.8807 (4) | 0.8101 (7) | 0.4164 (3) | 0.0284 (13) | |
H23 | 0.9036 | 0.8122 | 0.4672 | 0.034* | |
C24 | 0.9149 (3) | 0.7269 (7) | 0.3742 (3) | 0.0257 (13) | |
H24 | 0.9610 | 0.6731 | 0.3968 | 0.031* | |
C25 | 0.9924 (3) | 0.5681 (7) | 0.0864 (3) | 0.0239 (12) | |
H25A | 1.0208 | 0.4980 | 0.0633 | 0.029* | |
H25B | 0.9485 | 0.6125 | 0.0481 | 0.029* | |
C26 | 1.0396 (4) | 0.7150 (8) | 0.1260 (3) | 0.0321 (14) | |
H26A | 1.0111 | 0.7857 | 0.1480 | 0.048* | |
H26B | 1.0548 | 0.7833 | 0.0919 | 0.048* | |
H26C | 1.0832 | 0.6710 | 0.1637 | 0.048* | |
C27 | 0.8930 (3) | 0.3033 (7) | 0.0872 (3) | 0.0252 (13) | |
H27A | 0.8484 | 0.3715 | 0.0631 | 0.030* | |
H27B | 0.9111 | 0.2565 | 0.0496 | 0.030* | |
C28 | 0.8738 (4) | 0.1596 (9) | 0.1285 (4) | 0.0356 (15) | |
H28A | 0.9175 | 0.0893 | 0.1505 | 0.053* | |
H28B | 0.8348 | 0.0903 | 0.0954 | 0.053* | |
H28C | 0.8567 | 0.2060 | 0.1662 | 0.053* | |
C29 | 1.0927 (3) | 0.5749 (7) | 0.3692 (3) | 0.0246 (12) | |
H29A | 1.0747 | 0.6306 | 0.4052 | 0.030* | |
H29B | 1.1356 | 0.5036 | 0.3953 | 0.030* | |
C30 | 1.1156 (4) | 0.7083 (8) | 0.3256 (4) | 0.0370 (16) | |
H30A | 1.1325 | 0.6527 | 0.2895 | 0.055* | |
H30B | 1.1555 | 0.7770 | 0.3577 | 0.055* | |
H30C | 1.0734 | 0.7814 | 0.3013 | 0.055* | |
C31 | 0.9904 (3) | 0.3146 (8) | 0.3714 (3) | 0.0266 (13) | |
H31A | 1.0338 | 0.2640 | 0.4084 | 0.032* | |
H31B | 0.9642 | 0.3865 | 0.3960 | 0.032* | |
C32 | 0.9399 (4) | 0.1756 (9) | 0.3296 (4) | 0.0429 (18) | |
H32A | 0.8964 | 0.2264 | 0.2940 | 0.064* | |
H32B | 0.9247 | 0.1045 | 0.3628 | 0.064* | |
H32C | 0.9660 | 0.1059 | 0.3047 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt1 | 0.02093 (11) | 0.01524 (10) | 0.02032 (11) | 0.00053 (8) | 0.00548 (8) | 0.00055 (8) |
Pt2 | 0.02191 (11) | 0.01607 (10) | 0.02061 (11) | 0.00074 (8) | 0.00635 (8) | 0.00018 (8) |
S1 | 0.0227 (7) | 0.0160 (7) | 0.0206 (7) | 0.0007 (5) | 0.0059 (6) | 0.0004 (5) |
S2 | 0.0231 (7) | 0.0184 (7) | 0.0206 (7) | 0.0011 (5) | 0.0066 (6) | 0.0007 (5) |
C1 | 0.025 (3) | 0.016 (3) | 0.021 (3) | −0.002 (2) | 0.007 (2) | 0.002 (2) |
C2 | 0.021 (3) | 0.018 (3) | 0.020 (3) | −0.003 (2) | 0.006 (2) | 0.001 (2) |
C3 | 0.026 (3) | 0.016 (3) | 0.022 (3) | −0.004 (2) | 0.007 (2) | −0.001 (2) |
C4 | 0.023 (3) | 0.016 (3) | 0.024 (3) | −0.001 (2) | 0.008 (2) | 0.002 (2) |
C5 | 0.028 (3) | 0.015 (3) | 0.025 (3) | 0.002 (2) | 0.008 (2) | 0.002 (2) |
C6 | 0.030 (3) | 0.017 (3) | 0.023 (3) | −0.002 (2) | 0.009 (2) | 0.000 (2) |
C7 | 0.031 (3) | 0.019 (3) | 0.029 (3) | −0.001 (2) | 0.014 (3) | −0.003 (2) |
C8 | 0.026 (3) | 0.018 (3) | 0.030 (3) | 0.004 (2) | 0.010 (3) | 0.001 (2) |
C9 | 0.023 (3) | 0.013 (3) | 0.026 (3) | −0.003 (2) | 0.009 (2) | −0.001 (2) |
C10 | 0.030 (3) | 0.013 (3) | 0.021 (3) | −0.005 (2) | 0.010 (2) | 0.000 (2) |
C11 | 0.023 (3) | 0.017 (3) | 0.033 (3) | 0.002 (2) | 0.009 (3) | 0.002 (2) |
C12 | 0.027 (3) | 0.018 (3) | 0.029 (3) | 0.003 (2) | 0.003 (3) | 0.006 (2) |
C13 | 0.033 (3) | 0.018 (3) | 0.024 (3) | −0.002 (2) | 0.005 (3) | 0.001 (2) |
C14 | 0.026 (3) | 0.018 (3) | 0.030 (3) | −0.001 (2) | 0.009 (3) | 0.000 (2) |
C15 | 0.027 (3) | 0.016 (3) | 0.026 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
C16 | 0.026 (3) | 0.020 (3) | 0.024 (3) | −0.003 (2) | 0.006 (2) | 0.000 (2) |
C17 | 0.023 (3) | 0.020 (3) | 0.031 (3) | 0.003 (2) | 0.004 (3) | 0.003 (2) |
C18 | 0.027 (3) | 0.021 (3) | 0.028 (3) | 0.005 (2) | 0.007 (3) | −0.002 (2) |
C19 | 0.022 (3) | 0.015 (3) | 0.028 (3) | −0.002 (2) | 0.006 (2) | −0.003 (2) |
C20 | 0.024 (3) | 0.017 (3) | 0.029 (3) | 0.000 (2) | 0.011 (2) | 0.000 (2) |
C21 | 0.024 (3) | 0.021 (3) | 0.035 (3) | 0.003 (2) | 0.013 (3) | 0.001 (3) |
C22 | 0.034 (3) | 0.025 (3) | 0.029 (3) | −0.002 (3) | 0.016 (3) | −0.004 (3) |
C23 | 0.040 (4) | 0.022 (3) | 0.024 (3) | −0.001 (3) | 0.012 (3) | 0.001 (2) |
C24 | 0.030 (3) | 0.020 (3) | 0.026 (3) | 0.005 (2) | 0.009 (3) | 0.001 (2) |
C25 | 0.033 (3) | 0.018 (3) | 0.023 (3) | −0.001 (2) | 0.012 (3) | 0.000 (2) |
C26 | 0.040 (4) | 0.027 (3) | 0.031 (3) | −0.011 (3) | 0.014 (3) | 0.000 (3) |
C27 | 0.025 (3) | 0.020 (3) | 0.027 (3) | −0.005 (2) | 0.005 (2) | −0.005 (2) |
C28 | 0.037 (4) | 0.033 (4) | 0.034 (4) | −0.010 (3) | 0.009 (3) | 0.000 (3) |
C29 | 0.024 (3) | 0.022 (3) | 0.021 (3) | −0.001 (2) | −0.001 (2) | −0.005 (2) |
C30 | 0.039 (4) | 0.028 (3) | 0.037 (4) | −0.006 (3) | 0.003 (3) | 0.004 (3) |
C31 | 0.028 (3) | 0.027 (3) | 0.026 (3) | 0.002 (2) | 0.010 (3) | 0.004 (2) |
C32 | 0.060 (5) | 0.029 (4) | 0.045 (4) | −0.013 (3) | 0.026 (4) | −0.006 (3) |
Pt1—S1 | 2.3742 (14) | C16—H16 | 0.9500 |
Pt1—S2 | 2.3837 (14) | C16—C17 | 1.383 (8) |
Pt1—C1 | 2.028 (6) | C17—H17 | 0.9500 |
Pt1—C2 | 2.016 (5) | C17—C18 | 1.400 (8) |
Pt2—S1 | 2.3759 (14) | C18—H18 | 0.9500 |
Pt2—S2 | 2.3816 (14) | C18—C19 | 1.390 (8) |
Pt2—C3 | 2.021 (6) | C19—C20 | 1.482 (8) |
Pt2—C4 | 2.027 (6) | C20—C21 | 1.378 (8) |
S1—C25 | 1.812 (6) | C21—H21 | 0.9500 |
S1—C27 | 1.823 (6) | C21—C22 | 1.394 (8) |
S2—C29 | 1.823 (6) | C22—H22 | 0.9500 |
S2—C31 | 1.816 (6) | C22—C23 | 1.374 (9) |
C1—C5 | 1.396 (8) | C23—H23 | 0.9500 |
C1—C9 | 1.407 (8) | C23—C24 | 1.387 (8) |
C2—C10 | 1.419 (8) | C24—H24 | 0.9500 |
C2—C14 | 1.386 (8) | C25—H25A | 0.9900 |
C3—C15 | 1.394 (8) | C25—H25B | 0.9900 |
C3—C19 | 1.425 (8) | C25—C26 | 1.517 (8) |
C4—C20 | 1.403 (8) | C26—H26A | 0.9800 |
C4—C24 | 1.401 (8) | C26—H26B | 0.9800 |
C5—H5 | 0.9500 | C26—H26C | 0.9800 |
C5—C6 | 1.397 (8) | C27—H27A | 0.9900 |
C6—H6 | 0.9500 | C27—H27B | 0.9900 |
C6—C7 | 1.381 (8) | C27—C28 | 1.510 (8) |
C7—H7 | 0.9500 | C28—H28A | 0.9800 |
C7—C8 | 1.390 (8) | C28—H28B | 0.9800 |
C8—H8 | 0.9500 | C28—H28C | 0.9800 |
C8—C9 | 1.386 (8) | C29—H29A | 0.9900 |
C9—C10 | 1.478 (7) | C29—H29B | 0.9900 |
C10—C11 | 1.381 (8) | C29—C30 | 1.514 (8) |
C11—H11 | 0.9500 | C30—H30A | 0.9800 |
C11—C12 | 1.393 (8) | C30—H30B | 0.9800 |
C12—H12 | 0.9500 | C30—H30C | 0.9800 |
C12—C13 | 1.376 (8) | C31—H31A | 0.9900 |
C13—H13 | 0.9500 | C31—H31B | 0.9900 |
C13—C14 | 1.392 (8) | C31—C32 | 1.512 (9) |
C14—H14 | 0.9500 | C32—H32A | 0.9800 |
C15—H15 | 0.9500 | C32—H32B | 0.9800 |
C15—C16 | 1.396 (8) | C32—H32C | 0.9800 |
S1—Pt1—S2 | 78.08 (5) | C16—C17—H17 | 120.4 |
C1—Pt1—S1 | 100.76 (16) | C16—C17—C18 | 119.2 (5) |
C1—Pt1—S2 | 176.78 (16) | C18—C17—H17 | 120.4 |
C2—Pt1—S1 | 177.46 (16) | C17—C18—H18 | 119.8 |
C2—Pt1—S2 | 100.11 (16) | C19—C18—C17 | 120.4 (5) |
C2—Pt1—C1 | 80.9 (2) | C19—C18—H18 | 119.8 |
S1—Pt2—S2 | 78.09 (5) | C3—C19—C20 | 113.7 (5) |
C3—Pt2—S1 | 100.21 (16) | C18—C19—C3 | 121.2 (5) |
C3—Pt2—S2 | 176.99 (16) | C18—C19—C20 | 125.1 (5) |
C3—Pt2—C4 | 81.2 (2) | C4—C20—C19 | 114.4 (5) |
C4—Pt2—S1 | 177.17 (16) | C21—C20—C4 | 121.1 (6) |
C4—Pt2—S2 | 100.35 (16) | C21—C20—C19 | 124.4 (5) |
Pt1—S1—Pt2 | 102.14 (5) | C20—C21—H21 | 119.6 |
C25—S1—Pt1 | 112.0 (2) | C20—C21—C22 | 120.8 (6) |
C25—S1—Pt2 | 113.82 (19) | C22—C21—H21 | 119.6 |
C25—S1—C27 | 102.7 (3) | C21—C22—H22 | 120.6 |
C27—S1—Pt1 | 113.5 (2) | C23—C22—C21 | 118.8 (6) |
C27—S1—Pt2 | 113.1 (2) | C23—C22—H22 | 120.6 |
Pt2—S2—Pt1 | 101.69 (5) | C22—C23—H23 | 119.6 |
C29—S2—Pt1 | 111.5 (2) | C22—C23—C24 | 120.9 (6) |
C29—S2—Pt2 | 114.43 (19) | C24—C23—H23 | 119.6 |
C31—S2—Pt1 | 114.6 (2) | C4—C24—H24 | 119.4 |
C31—S2—Pt2 | 111.6 (2) | C23—C24—C4 | 121.1 (6) |
C31—S2—C29 | 103.5 (3) | C23—C24—H24 | 119.4 |
C5—C1—Pt1 | 127.2 (4) | S1—C25—H25A | 109.5 |
C5—C1—C9 | 117.4 (5) | S1—C25—H25B | 109.5 |
C9—C1—Pt1 | 115.3 (4) | H25A—C25—H25B | 108.1 |
C10—C2—Pt1 | 115.4 (4) | C26—C25—S1 | 110.7 (4) |
C14—C2—Pt1 | 127.8 (4) | C26—C25—H25A | 109.5 |
C14—C2—C10 | 116.7 (5) | C26—C25—H25B | 109.5 |
C15—C3—Pt2 | 128.2 (4) | C25—C26—H26A | 109.5 |
C15—C3—C19 | 116.7 (5) | C25—C26—H26B | 109.5 |
C19—C3—Pt2 | 115.0 (4) | C25—C26—H26C | 109.5 |
C20—C4—Pt2 | 115.3 (4) | H26A—C26—H26B | 109.5 |
C24—C4—Pt2 | 127.5 (4) | H26A—C26—H26C | 109.5 |
C24—C4—C20 | 117.2 (5) | H26B—C26—H26C | 109.5 |
C1—C5—H5 | 119.1 | S1—C27—H27A | 109.6 |
C1—C5—C6 | 121.8 (5) | S1—C27—H27B | 109.6 |
C6—C5—H5 | 119.1 | H27A—C27—H27B | 108.1 |
C5—C6—H6 | 120.2 | C28—C27—S1 | 110.4 (4) |
C7—C6—C5 | 119.5 (5) | C28—C27—H27A | 109.6 |
C7—C6—H6 | 120.2 | C28—C27—H27B | 109.6 |
C6—C7—H7 | 120.1 | C27—C28—H28A | 109.5 |
C6—C7—C8 | 119.8 (5) | C27—C28—H28B | 109.5 |
C8—C7—H7 | 120.1 | C27—C28—H28C | 109.5 |
C7—C8—H8 | 119.7 | H28A—C28—H28B | 109.5 |
C9—C8—C7 | 120.7 (5) | H28A—C28—H28C | 109.5 |
C9—C8—H8 | 119.7 | H28B—C28—H28C | 109.5 |
C1—C9—C10 | 114.2 (5) | S2—C29—H29A | 109.7 |
C8—C9—C1 | 120.7 (5) | S2—C29—H29B | 109.7 |
C8—C9—C10 | 125.1 (5) | H29A—C29—H29B | 108.2 |
C2—C10—C9 | 113.7 (5) | C30—C29—S2 | 109.8 (4) |
C11—C10—C2 | 121.1 (5) | C30—C29—H29A | 109.7 |
C11—C10—C9 | 125.1 (5) | C30—C29—H29B | 109.7 |
C10—C11—H11 | 119.7 | C29—C30—H30A | 109.5 |
C10—C11—C12 | 120.6 (5) | C29—C30—H30B | 109.5 |
C12—C11—H11 | 119.7 | C29—C30—H30C | 109.5 |
C11—C12—H12 | 120.5 | H30A—C30—H30B | 109.5 |
C13—C12—C11 | 119.0 (5) | H30A—C30—H30C | 109.5 |
C13—C12—H12 | 120.5 | H30B—C30—H30C | 109.5 |
C12—C13—H13 | 119.7 | S2—C31—H31A | 109.9 |
C12—C13—C14 | 120.5 (6) | S2—C31—H31B | 109.9 |
C14—C13—H13 | 119.7 | H31A—C31—H31B | 108.3 |
C2—C14—C13 | 121.9 (6) | C32—C31—S2 | 109.1 (4) |
C2—C14—H14 | 119.0 | C32—C31—H31A | 109.9 |
C13—C14—H14 | 119.0 | C32—C31—H31B | 109.9 |
C3—C15—H15 | 119.0 | C31—C32—H32A | 109.5 |
C3—C15—C16 | 122.1 (5) | C31—C32—H32B | 109.5 |
C16—C15—H15 | 119.0 | C31—C32—H32C | 109.5 |
C15—C16—H16 | 119.8 | H32A—C32—H32B | 109.5 |
C17—C16—C15 | 120.4 (5) | H32A—C32—H32C | 109.5 |
C17—C16—H16 | 119.8 | H32B—C32—H32C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Pt2(C12H10)2(C4H8S)2] |
Mr | 874.91 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 19.2938 (15), 7.8839 (6), 19.6969 (17) |
β (°) | 109.639 (5) |
V (Å3) | 2821.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 10.07 |
Crystal size (mm) | 0.05 × 0.02 × 0.01 |
Data collection | |
Diffractometer | Bruker APEXII Ultra |
Absorption correction | Multi-scan (SADABS; Bruker, 2015) |
Tmin, Tmax | 0.018, 0.048 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 39433, 6763, 5668 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.066, 1.10 |
No. of reflections | 6763 |
No. of parameters | 329 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0141P)2 + 15.5401P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.93, −1.80 |
Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2012), SHELXT (Sheldrick, 2015a), SHELXL2015 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
We are grateful for support from the National Science Foundation (EPSCoR), the Wichita State University Office of Research Administration, and the Department of Energy.
References
Bruker (2012). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2013). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2015). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Brune, H.-A., Roth, H., Debaerdemaeker, T. & Schible, H.-M. (1991). J. Organomet. Chem. 402, 435–442. CSD CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Escola, A., Crespo, M., Quirante, J., Cortes, R., Jayaraman, A., Badia, J., Calvet, T., Font-Bardia, M. & Cascante, M. (2014). Organometallics, 33, 1740–1750. CAS Google Scholar
Gardner, S. A., Gordon, H. B. & Rausch, M. P. (1973). J. Organomet. Chem. 60, 179–188. CrossRef CAS Google Scholar
Gilman, H. & Gaj, H. J. (1957). J. Org. Chem. 22, 447–449. CrossRef CAS Google Scholar
Rillema, D. P., Cruz, A. J., Tasset, B. J., Moore, C., Siam, K. & Huang, W. (2013). J. Mol. Struct. 1041, 82–91. CSD CrossRef CAS Google Scholar
Rillema, D. P., Stoyanov, S., Cruz, A., Huag, W., Moore, C., Siam, K., Jehan, A. & Nguyen, T. (2015). Dalton Trans. 44, 17075–17090. CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.