metal-organic compounds
trans-Bis(benzyldiphenylphosphane-κP)dichloridoplatinum(II)
aResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
*Correspondence e-mail: mullera@uj.ac.za
In the mononuclear title compound, trans-[PtCl2(C19H17P)2], the slightly distorted square-planar coordination sphere of the PtII atom is occupied by two benzyldiphenylphosphane ligands and two chloride atoms in a mutually trans geometry. The effective cone angles for the two phosphane ligands are 160 and 169°. C—H⋯Cl interactions generate infinite long chains along [01-1]. Additional C—H⋯π and π–π stacking interactions [centroid–centroid distance = 4.2499 (15) Å and ring slippage = 2.386 Å] are observed.
Related literature
For reviews of related compounds, see: Spessard & Miessler (1996); Muller & Meijboom (2010). For background to cone angles, see: Tolman (1977); Otto (2001). For the cis isomer of the title compound, see: Davis & Meijboom (2011).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2011); cell SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).
Supporting information
10.1107/S160053681204696X/ng5305sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681204696X/ng5305Isup2.hkl
Potassium trichloro(ethylene)platinate(II) (10 mg, 0.0271 mmol) and benzyldiphenylphosphane (7.5 mg, 0.0271 mmol) were dissolved seperately in acetone (10 ml) and the latter added drop-wise to the other with stirring at room temperature (10 min). Slow evaporation of the solvent gave colourless crystals of the title compound suitable for a single-crystal X-ray diffraction study. Analytical data: 31P {H} NMR (CDCl3, 161.99 MHz): d = 13.58 (t, 1J(31P-195Pt) = 2308 Hz).
The aromatic and methylene H atoms were placed in geometrically idealized positions (C—H = 0.95–0.99) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The highest residual electron density (< 1 Å3) are within 1 Å from Pt and represent no physical meaning.
Data collection: APEX2 (Bruker, 2011); cell
SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).Fig. 1. A view of the title complex, showing the atom-numbering scheme and 50% probability displacement ellipsoids. Hydrogen atoms have been omitted for clarity. | |
Fig. 2. Packing diagram showing only the C—H···Cl interactions (indicated by red dashed lines). | |
Fig. 3. Packing diagram showing only the C—H···π interactions as well as π···π stacking (both indicated by red dashed lines). |
[PtCl2(C19H17P)2] | Z = 2 |
Mr = 818.58 | F(000) = 808 |
Triclinic, P1 | Dx = 1.647 Mg m−3 Dm = 1.647 Mg m−3 Dm measured by not measured |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5585 (12) Å | Cell parameters from 9225 reflections |
b = 13.4135 (17) Å | θ = 2.6–28.4° |
c = 14.7553 (18) Å | µ = 4.54 mm−1 |
α = 66.307 (2)° | T = 100 K |
β = 73.147 (3)° | Needle, colourless |
γ = 88.034 (3)° | 0.24 × 0.1 × 0.08 mm |
V = 1650.7 (4) Å3 |
Bruker APEX DUO 4K CCD diffractometer | 8253 independent reflections |
Radiation source: sealed tube | 7779 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.4 pixels mm-1 | θmax = 28.4°, θmin = 1.6° |
ϕ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | k = −17→17 |
Tmin = 0.409, Tmax = 0.713 | l = −19→19 |
33198 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)] = 0.018 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.039 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0157P)2 + 0.6462P] where P = (Fo2 + 2Fc2)/3 |
8253 reflections | (Δ/σ)max = 0.002 |
388 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
[PtCl2(C19H17P)2] | γ = 88.034 (3)° |
Mr = 818.58 | V = 1650.7 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.5585 (12) Å | Mo Kα radiation |
b = 13.4135 (17) Å | µ = 4.54 mm−1 |
c = 14.7553 (18) Å | T = 100 K |
α = 66.307 (2)° | 0.24 × 0.1 × 0.08 mm |
β = 73.147 (3)° |
Bruker APEX DUO 4K CCD diffractometer | 8253 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 7779 reflections with I > 2σ(I) |
Tmin = 0.409, Tmax = 0.713 | Rint = 0.031 |
33198 measured reflections |
R[F2 > 2σ(F2)] = 0.018 | 0 restraints |
wR(F2) = 0.039 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.65 e Å−3 |
8253 reflections | Δρmin = −0.54 e Å−3 |
388 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Pt1 | 0.435237 (8) | 0.254343 (6) | 0.260155 (5) | 0.00938 (2) | |
Cl1 | 0.32010 (6) | 0.39062 (4) | 0.16068 (4) | 0.01605 (10) | |
Cl2 | 0.57602 (5) | 0.12862 (4) | 0.34467 (4) | 0.01508 (9) | |
P1 | 0.49965 (6) | 0.36874 (4) | 0.32689 (4) | 0.01070 (10) | |
P2 | 0.39698 (6) | 0.14486 (4) | 0.18021 (4) | 0.01132 (10) | |
C1 | 0.5284 (2) | 0.30979 (16) | 0.45596 (14) | 0.0133 (4) | |
H1A | 0.5961 | 0.252 | 0.4572 | 0.016* | |
H1B | 0.579 | 0.3679 | 0.4636 | 0.016* | |
C2 | 0.3947 (2) | 0.26114 (16) | 0.54973 (14) | 0.0136 (4) | |
C3 | 0.3107 (2) | 0.32666 (17) | 0.59474 (16) | 0.0173 (4) | |
H3 | 0.3307 | 0.4039 | 0.5611 | 0.021* | |
C4 | 0.1986 (2) | 0.27982 (18) | 0.68797 (16) | 0.0196 (4) | |
H4 | 0.1428 | 0.325 | 0.7178 | 0.023* | |
C5 | 0.1682 (2) | 0.16662 (18) | 0.73760 (16) | 0.0194 (4) | |
H5 | 0.093 | 0.1344 | 0.8021 | 0.023* | |
C6 | 0.2477 (2) | 0.10114 (17) | 0.69279 (16) | 0.0191 (4) | |
H6 | 0.2257 | 0.024 | 0.7261 | 0.023* | |
C7 | 0.3599 (2) | 0.14780 (16) | 0.59903 (15) | 0.0163 (4) | |
H7 | 0.413 | 0.1023 | 0.5684 | 0.02* | |
C8 | 0.3766 (2) | 0.47250 (15) | 0.33790 (14) | 0.0129 (4) | |
C9 | 0.2264 (2) | 0.44601 (16) | 0.36676 (15) | 0.0155 (4) | |
H9 | 0.1906 | 0.3779 | 0.3725 | 0.019* | |
C10 | 0.1284 (3) | 0.51857 (18) | 0.38729 (16) | 0.0206 (5) | |
H10 | 0.0257 | 0.5004 | 0.4063 | 0.025* | |
C11 | 0.1805 (3) | 0.61791 (18) | 0.38000 (16) | 0.0232 (5) | |
H11 | 0.1135 | 0.667 | 0.3955 | 0.028* | |
C12 | 0.3307 (3) | 0.64529 (17) | 0.34999 (17) | 0.0233 (5) | |
H12 | 0.3664 | 0.7135 | 0.3443 | 0.028* | |
C13 | 0.4290 (3) | 0.57345 (16) | 0.32830 (16) | 0.0178 (4) | |
H13 | 0.5317 | 0.5928 | 0.307 | 0.021* | |
C14 | 0.6772 (2) | 0.44094 (15) | 0.24140 (15) | 0.0130 (4) | |
C15 | 0.6881 (2) | 0.50991 (17) | 0.13829 (16) | 0.0186 (4) | |
H15 | 0.6028 | 0.5205 | 0.116 | 0.022* | |
C16 | 0.8220 (3) | 0.56263 (18) | 0.06883 (17) | 0.0220 (5) | |
H16 | 0.8277 | 0.6108 | −0.0004 | 0.026* | |
C17 | 0.9486 (2) | 0.54559 (18) | 0.09962 (17) | 0.0210 (5) | |
H17 | 1.0408 | 0.5812 | 0.0515 | 0.025* | |
C18 | 0.9389 (2) | 0.47609 (18) | 0.20123 (17) | 0.0212 (5) | |
H18 | 1.025 | 0.4641 | 0.2225 | 0.025* | |
C19 | 0.8044 (2) | 0.42395 (17) | 0.27196 (16) | 0.0182 (4) | |
H19 | 0.799 | 0.3766 | 0.3413 | 0.022* | |
C27 | 0.5508 (2) | 0.17383 (16) | 0.06288 (14) | 0.0132 (4) | |
C32 | 0.6258 (2) | 0.09293 (17) | 0.03745 (16) | 0.0179 (4) | |
H32 | 0.5979 | 0.018 | 0.0827 | 0.021* | |
C31 | 0.7414 (2) | 0.12179 (17) | −0.05392 (16) | 0.0192 (4) | |
H31 | 0.7925 | 0.0665 | −0.0707 | 0.023* | |
C30 | 0.7826 (2) | 0.23148 (17) | −0.12105 (15) | 0.0180 (4) | |
H30 | 0.8613 | 0.251 | −0.1836 | 0.022* | |
C29 | 0.7083 (2) | 0.31196 (17) | −0.09620 (15) | 0.0182 (4) | |
H29 | 0.7354 | 0.3867 | −0.1422 | 0.022* | |
C28 | 0.5946 (2) | 0.28397 (16) | −0.00462 (15) | 0.0169 (4) | |
H28 | 0.5458 | 0.3398 | 0.0126 | 0.02* | |
C33 | 0.2343 (2) | 0.16194 (15) | 0.13646 (15) | 0.0138 (4) | |
C38 | 0.2353 (3) | 0.15109 (17) | 0.04602 (17) | 0.0205 (5) | |
H38 | 0.3239 | 0.1398 | 0.0028 | 0.025* | |
C37 | 0.1054 (3) | 0.1569 (2) | 0.01952 (19) | 0.0282 (5) | |
H37 | 0.1057 | 0.1486 | −0.0415 | 0.034* | |
C36 | −0.0239 (3) | 0.17476 (18) | 0.08137 (17) | 0.0239 (5) | |
H36 | −0.1117 | 0.1786 | 0.0627 | 0.029* | |
C35 | −0.0251 (2) | 0.18690 (18) | 0.17016 (17) | 0.0225 (5) | |
H35 | −0.1135 | 0.1996 | 0.2125 | 0.027* | |
C34 | 0.1039 (2) | 0.18053 (18) | 0.19755 (16) | 0.0198 (4) | |
H34 | 0.1027 | 0.189 | 0.2587 | 0.024* | |
C20 | 0.3854 (2) | −0.00427 (15) | 0.25407 (15) | 0.0139 (4) | |
H20A | 0.3845 | −0.0401 | 0.2072 | 0.017* | |
H20B | 0.4752 | −0.0223 | 0.2758 | 0.017* | |
C21 | 0.2533 (2) | −0.05230 (15) | 0.34940 (15) | 0.0133 (4) | |
C26 | 0.2527 (2) | −0.05270 (17) | 0.44434 (15) | 0.0173 (4) | |
H26 | 0.3344 | −0.0185 | 0.4488 | 0.021* | |
C25 | 0.1336 (3) | −0.10261 (19) | 0.53223 (16) | 0.0231 (5) | |
H25 | 0.1345 | −0.1027 | 0.5965 | 0.028* | |
C24 | 0.0128 (2) | −0.15251 (18) | 0.52703 (16) | 0.0203 (4) | |
H24 | −0.0683 | −0.1871 | 0.5875 | 0.024* | |
C23 | 0.0117 (2) | −0.15134 (17) | 0.43293 (16) | 0.0184 (4) | |
H23 | −0.0705 | −0.1851 | 0.4287 | 0.022* | |
C22 | 0.1304 (2) | −0.10102 (16) | 0.34484 (15) | 0.0167 (4) | |
H22 | 0.1279 | −0.0997 | 0.2805 | 0.02* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt1 | 0.00944 (4) | 0.00964 (4) | 0.00983 (4) | 0.00115 (2) | −0.00353 (3) | −0.00432 (3) |
Cl1 | 0.0197 (3) | 0.0158 (2) | 0.0176 (2) | 0.00698 (19) | −0.0111 (2) | −0.00844 (18) |
Cl2 | 0.0158 (2) | 0.0131 (2) | 0.0189 (2) | 0.00403 (18) | −0.00962 (19) | −0.00633 (18) |
P1 | 0.0105 (2) | 0.0112 (2) | 0.0106 (2) | 0.00044 (18) | −0.00338 (19) | −0.00455 (18) |
P2 | 0.0119 (3) | 0.0115 (2) | 0.0102 (2) | −0.00023 (19) | −0.00265 (19) | −0.00438 (18) |
C1 | 0.0133 (10) | 0.0147 (9) | 0.0117 (9) | 0.0004 (8) | −0.0048 (8) | −0.0046 (7) |
C2 | 0.0139 (10) | 0.0171 (9) | 0.0105 (8) | 0.0010 (8) | −0.0062 (8) | −0.0046 (7) |
C3 | 0.0201 (11) | 0.0181 (10) | 0.0171 (10) | 0.0013 (8) | −0.0070 (9) | −0.0095 (8) |
C4 | 0.0183 (11) | 0.0269 (11) | 0.0200 (10) | 0.0054 (9) | −0.0067 (9) | −0.0155 (9) |
C5 | 0.0149 (11) | 0.0285 (11) | 0.0134 (9) | −0.0006 (9) | −0.0037 (8) | −0.0074 (8) |
C6 | 0.0171 (11) | 0.0179 (10) | 0.0177 (10) | 0.0005 (8) | −0.0052 (9) | −0.0027 (8) |
C7 | 0.0122 (10) | 0.0180 (10) | 0.0171 (9) | 0.0033 (8) | −0.0037 (8) | −0.0063 (8) |
C8 | 0.0162 (10) | 0.0139 (9) | 0.0099 (8) | 0.0034 (8) | −0.0046 (8) | −0.0060 (7) |
C9 | 0.0171 (11) | 0.0163 (9) | 0.0119 (9) | 0.0006 (8) | −0.0028 (8) | −0.0055 (7) |
C10 | 0.0186 (11) | 0.0271 (11) | 0.0138 (9) | 0.0069 (9) | −0.0030 (8) | −0.0079 (8) |
C11 | 0.0315 (14) | 0.0231 (11) | 0.0164 (10) | 0.0127 (10) | −0.0058 (9) | −0.0112 (9) |
C12 | 0.0383 (15) | 0.0157 (10) | 0.0199 (10) | 0.0062 (9) | −0.0118 (10) | −0.0094 (8) |
C13 | 0.0223 (12) | 0.0155 (10) | 0.0183 (10) | 0.0008 (8) | −0.0095 (9) | −0.0073 (8) |
C14 | 0.0128 (10) | 0.0128 (9) | 0.0139 (9) | −0.0001 (7) | −0.0029 (8) | −0.0066 (7) |
C15 | 0.0170 (11) | 0.0198 (10) | 0.0169 (10) | −0.0003 (8) | −0.0065 (8) | −0.0043 (8) |
C16 | 0.0220 (12) | 0.0215 (11) | 0.0168 (10) | −0.0037 (9) | −0.0052 (9) | −0.0023 (8) |
C17 | 0.0161 (11) | 0.0218 (11) | 0.0203 (10) | −0.0048 (9) | 0.0008 (9) | −0.0078 (9) |
C18 | 0.0142 (11) | 0.0262 (11) | 0.0229 (11) | 0.0000 (9) | −0.0067 (9) | −0.0088 (9) |
C19 | 0.0173 (11) | 0.0193 (10) | 0.0170 (10) | 0.0009 (8) | −0.0068 (8) | −0.0053 (8) |
C27 | 0.0108 (10) | 0.0177 (9) | 0.0109 (8) | −0.0008 (8) | −0.0016 (7) | −0.0068 (7) |
C32 | 0.0206 (11) | 0.0139 (9) | 0.0174 (10) | −0.0004 (8) | −0.0040 (9) | −0.0056 (8) |
C31 | 0.0199 (12) | 0.0189 (10) | 0.0197 (10) | 0.0030 (9) | −0.0036 (9) | −0.0107 (8) |
C30 | 0.0143 (11) | 0.0249 (11) | 0.0128 (9) | 0.0003 (8) | −0.0013 (8) | −0.0073 (8) |
C29 | 0.0181 (11) | 0.0168 (10) | 0.0148 (9) | −0.0005 (8) | −0.0027 (8) | −0.0031 (8) |
C28 | 0.0185 (11) | 0.0153 (9) | 0.0160 (9) | 0.0022 (8) | −0.0033 (8) | −0.0070 (8) |
C33 | 0.0152 (10) | 0.0108 (9) | 0.0147 (9) | −0.0023 (7) | −0.0058 (8) | −0.0036 (7) |
C38 | 0.0261 (12) | 0.0218 (11) | 0.0203 (10) | 0.0071 (9) | −0.0104 (9) | −0.0132 (9) |
C37 | 0.0375 (15) | 0.0330 (13) | 0.0278 (12) | 0.0054 (11) | −0.0217 (11) | −0.0180 (10) |
C36 | 0.0221 (12) | 0.0231 (11) | 0.0263 (11) | −0.0044 (9) | −0.0147 (10) | −0.0043 (9) |
C35 | 0.0130 (11) | 0.0274 (11) | 0.0197 (10) | −0.0026 (9) | −0.0027 (9) | −0.0034 (9) |
C34 | 0.0168 (11) | 0.0274 (11) | 0.0118 (9) | −0.0046 (9) | −0.0032 (8) | −0.0049 (8) |
C20 | 0.0153 (10) | 0.0125 (9) | 0.0130 (9) | 0.0015 (8) | −0.0033 (8) | −0.0051 (7) |
C21 | 0.0151 (10) | 0.0098 (8) | 0.0132 (9) | 0.0025 (7) | −0.0034 (8) | −0.0037 (7) |
C26 | 0.0171 (11) | 0.0190 (10) | 0.0158 (9) | −0.0020 (8) | −0.0059 (8) | −0.0063 (8) |
C25 | 0.0237 (12) | 0.0324 (12) | 0.0131 (9) | −0.0044 (10) | −0.0041 (9) | −0.0096 (9) |
C24 | 0.0164 (11) | 0.0257 (11) | 0.0159 (10) | −0.0043 (9) | −0.0002 (8) | −0.0084 (8) |
C23 | 0.0175 (11) | 0.0189 (10) | 0.0191 (10) | −0.0017 (8) | −0.0053 (9) | −0.0079 (8) |
C22 | 0.0206 (11) | 0.0165 (10) | 0.0135 (9) | −0.0019 (8) | −0.0055 (8) | −0.0059 (8) |
Pt1—P1 | 2.3096 (5) | C17—C18 | 1.388 (3) |
Pt1—Cl2 | 2.3102 (5) | C17—H17 | 0.95 |
Pt1—Cl1 | 2.3128 (5) | C18—C19 | 1.388 (3) |
Pt1—P2 | 2.3155 (5) | C18—H18 | 0.95 |
P1—C14 | 1.817 (2) | C19—H19 | 0.95 |
P1—C8 | 1.818 (2) | C27—C32 | 1.397 (3) |
P1—C1 | 1.8456 (19) | C27—C28 | 1.403 (3) |
P2—C33 | 1.824 (2) | C32—C31 | 1.391 (3) |
P2—C27 | 1.825 (2) | C32—H32 | 0.95 |
P2—C20 | 1.8424 (19) | C31—C30 | 1.394 (3) |
C1—C2 | 1.510 (3) | C31—H31 | 0.95 |
C1—H1A | 0.99 | C30—C29 | 1.385 (3) |
C1—H1B | 0.99 | C30—H30 | 0.95 |
C2—C7 | 1.399 (3) | C29—C28 | 1.385 (3) |
C2—C3 | 1.403 (3) | C29—H29 | 0.95 |
C3—C4 | 1.390 (3) | C28—H28 | 0.95 |
C3—H3 | 0.95 | C33—C34 | 1.391 (3) |
C4—C5 | 1.393 (3) | C33—C38 | 1.396 (3) |
C4—H4 | 0.95 | C38—C37 | 1.397 (3) |
C5—C6 | 1.384 (3) | C38—H38 | 0.95 |
C5—H5 | 0.95 | C37—C36 | 1.385 (4) |
C6—C7 | 1.395 (3) | C37—H37 | 0.95 |
C6—H6 | 0.95 | C36—C35 | 1.381 (3) |
C7—H7 | 0.95 | C36—H36 | 0.95 |
C8—C9 | 1.388 (3) | C35—C34 | 1.394 (3) |
C8—C13 | 1.398 (3) | C35—H35 | 0.95 |
C9—C10 | 1.388 (3) | C34—H34 | 0.95 |
C9—H9 | 0.95 | C20—C21 | 1.512 (3) |
C10—C11 | 1.391 (3) | C20—H20A | 0.99 |
C10—H10 | 0.95 | C20—H20B | 0.99 |
C11—C12 | 1.389 (3) | C21—C22 | 1.395 (3) |
C11—H11 | 0.95 | C21—C26 | 1.397 (3) |
C12—C13 | 1.387 (3) | C26—C25 | 1.387 (3) |
C12—H12 | 0.95 | C26—H26 | 0.95 |
C13—H13 | 0.95 | C25—C24 | 1.390 (3) |
C14—C19 | 1.396 (3) | C25—H25 | 0.95 |
C14—C15 | 1.402 (3) | C24—C23 | 1.385 (3) |
C15—C16 | 1.381 (3) | C24—H24 | 0.95 |
C15—H15 | 0.95 | C23—C22 | 1.387 (3) |
C16—C17 | 1.393 (3) | C23—H23 | 0.95 |
C16—H16 | 0.95 | C22—H22 | 0.95 |
P1—Pt1—Cl2 | 87.718 (19) | C18—C17—C16 | 119.4 (2) |
P1—Pt1—Cl1 | 91.019 (19) | C18—C17—H17 | 120.3 |
Cl2—Pt1—Cl1 | 173.220 (18) | C16—C17—H17 | 120.3 |
P1—Pt1—P2 | 173.566 (18) | C17—C18—C19 | 120.6 (2) |
Cl2—Pt1—P2 | 90.665 (19) | C17—C18—H18 | 119.7 |
Cl1—Pt1—P2 | 89.858 (19) | C19—C18—H18 | 119.7 |
C14—P1—C8 | 106.61 (9) | C18—C19—C14 | 120.17 (19) |
C14—P1—C1 | 103.09 (9) | C18—C19—H19 | 119.9 |
C8—P1—C1 | 101.91 (9) | C14—C19—H19 | 119.9 |
C14—P1—Pt1 | 107.53 (7) | C32—C27—C28 | 118.98 (18) |
C8—P1—Pt1 | 116.64 (7) | C32—C27—P2 | 123.67 (15) |
C1—P1—Pt1 | 119.65 (7) | C28—C27—P2 | 117.34 (15) |
C33—P2—C27 | 104.68 (9) | C31—C32—C27 | 120.15 (19) |
C33—P2—C20 | 102.65 (9) | C31—C32—H32 | 119.9 |
C27—P2—C20 | 104.59 (9) | C27—C32—H32 | 119.9 |
C33—P2—Pt1 | 117.37 (7) | C32—C31—C30 | 120.3 (2) |
C27—P2—Pt1 | 108.96 (7) | C32—C31—H31 | 119.8 |
C20—P2—Pt1 | 117.20 (7) | C30—C31—H31 | 119.8 |
C2—C1—P1 | 117.65 (14) | C29—C30—C31 | 119.70 (19) |
C2—C1—H1A | 107.9 | C29—C30—H30 | 120.1 |
P1—C1—H1A | 107.9 | C31—C30—H30 | 120.1 |
C2—C1—H1B | 107.9 | C28—C29—C30 | 120.32 (19) |
P1—C1—H1B | 107.9 | C28—C29—H29 | 119.8 |
H1A—C1—H1B | 107.2 | C30—C29—H29 | 119.8 |
C7—C2—C3 | 118.48 (19) | C29—C28—C27 | 120.50 (19) |
C7—C2—C1 | 120.09 (18) | C29—C28—H28 | 119.7 |
C3—C2—C1 | 121.19 (18) | C27—C28—H28 | 119.7 |
C4—C3—C2 | 120.78 (19) | C34—C33—C38 | 119.19 (19) |
C4—C3—H3 | 119.6 | C34—C33—P2 | 119.13 (15) |
C2—C3—H3 | 119.6 | C38—C33—P2 | 121.60 (17) |
C3—C4—C5 | 120.0 (2) | C33—C38—C37 | 119.6 (2) |
C3—C4—H4 | 120 | C33—C38—H38 | 120.2 |
C5—C4—H4 | 120 | C37—C38—H38 | 120.2 |
C6—C5—C4 | 119.9 (2) | C36—C37—C38 | 120.6 (2) |
C6—C5—H5 | 120.1 | C36—C37—H37 | 119.7 |
C4—C5—H5 | 120.1 | C38—C37—H37 | 119.7 |
C5—C6—C7 | 120.4 (2) | C35—C36—C37 | 120.0 (2) |
C5—C6—H6 | 119.8 | C35—C36—H36 | 120 |
C7—C6—H6 | 119.8 | C37—C36—H36 | 120 |
C6—C7—C2 | 120.5 (2) | C36—C35—C34 | 119.8 (2) |
C6—C7—H7 | 119.8 | C36—C35—H35 | 120.1 |
C2—C7—H7 | 119.8 | C34—C35—H35 | 120.1 |
C9—C8—C13 | 119.65 (19) | C33—C34—C35 | 120.8 (2) |
C9—C8—P1 | 118.67 (15) | C33—C34—H34 | 119.6 |
C13—C8—P1 | 121.35 (16) | C35—C34—H34 | 119.6 |
C8—C9—C10 | 120.4 (2) | C21—C20—P2 | 115.37 (14) |
C8—C9—H9 | 119.8 | C21—C20—H20A | 108.4 |
C10—C9—H9 | 119.8 | P2—C20—H20A | 108.4 |
C9—C10—C11 | 119.9 (2) | C21—C20—H20B | 108.4 |
C9—C10—H10 | 120 | P2—C20—H20B | 108.4 |
C11—C10—H10 | 120 | H20A—C20—H20B | 107.5 |
C12—C11—C10 | 119.9 (2) | C22—C21—C26 | 118.42 (18) |
C12—C11—H11 | 120 | C22—C21—C20 | 120.11 (17) |
C10—C11—H11 | 120 | C26—C21—C20 | 121.43 (18) |
C13—C12—C11 | 120.3 (2) | C25—C26—C21 | 120.50 (19) |
C13—C12—H12 | 119.9 | C25—C26—H26 | 119.8 |
C11—C12—H12 | 119.9 | C21—C26—H26 | 119.8 |
C12—C13—C8 | 119.9 (2) | C26—C25—C24 | 120.50 (19) |
C12—C13—H13 | 120.1 | C26—C25—H25 | 119.8 |
C8—C13—H13 | 120.1 | C24—C25—H25 | 119.8 |
C19—C14—C15 | 118.98 (19) | C23—C24—C25 | 119.4 (2) |
C19—C14—P1 | 122.68 (15) | C23—C24—H24 | 120.3 |
C15—C14—P1 | 118.15 (15) | C25—C24—H24 | 120.3 |
C16—C15—C14 | 120.5 (2) | C24—C23—C22 | 120.2 (2) |
C16—C15—H15 | 119.8 | C24—C23—H23 | 119.9 |
C14—C15—H15 | 119.8 | C22—C23—H23 | 119.9 |
C15—C16—C17 | 120.38 (19) | C23—C22—C21 | 120.96 (18) |
C15—C16—H16 | 119.8 | C23—C22—H22 | 119.5 |
C17—C16—H16 | 119.8 | C21—C22—H22 | 119.5 |
Cl2—Pt1—P1—C14 | 83.74 (7) | C14—C15—C16—C17 | 1.8 (3) |
Cl1—Pt1—P1—C14 | −89.59 (7) | C15—C16—C17—C18 | −0.8 (3) |
Cl2—Pt1—P1—C8 | −156.67 (7) | C16—C17—C18—C19 | −0.1 (3) |
Cl1—Pt1—P1—C8 | 30.00 (7) | C17—C18—C19—C14 | 0.0 (3) |
Cl2—Pt1—P1—C1 | −33.21 (8) | C15—C14—C19—C18 | 0.9 (3) |
Cl1—Pt1—P1—C1 | 153.46 (8) | P1—C14—C19—C18 | 175.77 (17) |
Cl2—Pt1—P2—C33 | 156.19 (7) | C33—P2—C27—C32 | −101.79 (18) |
Cl1—Pt1—P2—C33 | −30.57 (7) | C20—P2—C27—C32 | 5.8 (2) |
Cl2—Pt1—P2—C27 | −85.16 (7) | Pt1—P2—C27—C32 | 131.87 (16) |
Cl1—Pt1—P2—C27 | 88.08 (7) | C33—P2—C27—C28 | 78.23 (17) |
Cl2—Pt1—P2—C20 | 33.27 (8) | C20—P2—C27—C28 | −174.18 (16) |
Cl1—Pt1—P2—C20 | −153.49 (8) | Pt1—P2—C27—C28 | −48.10 (17) |
C14—P1—C1—C2 | 168.80 (15) | C28—C27—C32—C31 | −0.5 (3) |
C8—P1—C1—C2 | 58.37 (17) | P2—C27—C32—C31 | 179.56 (16) |
Pt1—P1—C1—C2 | −71.98 (16) | C27—C32—C31—C30 | −0.4 (3) |
P1—C1—C2—C7 | 100.76 (19) | C32—C31—C30—C29 | 0.3 (3) |
P1—C1—C2—C3 | −85.0 (2) | C31—C30—C29—C28 | 0.7 (3) |
C7—C2—C3—C4 | 2.1 (3) | C30—C29—C28—C27 | −1.6 (3) |
C1—C2—C3—C4 | −172.26 (18) | C32—C27—C28—C29 | 1.5 (3) |
C2—C3—C4—C5 | −0.3 (3) | P2—C27—C28—C29 | −178.56 (16) |
C3—C4—C5—C6 | −1.4 (3) | C27—P2—C33—C34 | −159.45 (16) |
C4—C5—C6—C7 | 1.1 (3) | C20—P2—C33—C34 | 91.54 (17) |
C5—C6—C7—C2 | 0.8 (3) | Pt1—P2—C33—C34 | −38.53 (18) |
C3—C2—C7—C6 | −2.4 (3) | C27—P2—C33—C38 | 23.99 (19) |
C1—C2—C7—C6 | 172.07 (18) | C20—P2—C33—C38 | −85.02 (18) |
C14—P1—C8—C9 | 157.60 (15) | Pt1—P2—C33—C38 | 144.91 (15) |
C1—P1—C8—C9 | −94.68 (16) | C34—C33—C38—C37 | −1.2 (3) |
Pt1—P1—C8—C9 | 37.51 (17) | P2—C33—C38—C37 | 175.32 (17) |
C14—P1—C8—C13 | −28.96 (18) | C33—C38—C37—C36 | 0.8 (3) |
C1—P1—C8—C13 | 78.77 (17) | C38—C37—C36—C35 | 0.0 (4) |
Pt1—P1—C8—C13 | −149.04 (14) | C37—C36—C35—C34 | −0.4 (3) |
C13—C8—C9—C10 | −0.8 (3) | C38—C33—C34—C35 | 0.9 (3) |
P1—C8—C9—C10 | 172.78 (15) | P2—C33—C34—C35 | −175.79 (16) |
C8—C9—C10—C11 | −0.7 (3) | C36—C35—C34—C33 | −0.1 (3) |
C9—C10—C11—C12 | 1.4 (3) | C33—P2—C20—C21 | −63.36 (16) |
C10—C11—C12—C13 | −0.7 (3) | C27—P2—C20—C21 | −172.43 (14) |
C11—C12—C13—C8 | −0.8 (3) | Pt1—P2—C20—C21 | 66.82 (16) |
C9—C8—C13—C12 | 1.5 (3) | P2—C20—C21—C22 | 98.4 (2) |
P1—C8—C13—C12 | −171.87 (15) | P2—C20—C21—C26 | −83.9 (2) |
C8—P1—C14—C19 | 121.64 (18) | C22—C21—C26—C25 | 1.4 (3) |
C1—P1—C14—C19 | 14.8 (2) | C20—C21—C26—C25 | −176.4 (2) |
Pt1—P1—C14—C19 | −112.56 (17) | C21—C26—C25—C24 | −0.3 (3) |
C8—P1—C14—C15 | −63.45 (18) | C26—C25—C24—C23 | −0.5 (3) |
C1—P1—C14—C15 | −170.34 (16) | C25—C24—C23—C22 | 0.2 (3) |
Pt1—P1—C14—C15 | 62.34 (17) | C24—C23—C22—C21 | 1.0 (3) |
C19—C14—C15—C16 | −1.8 (3) | C26—C21—C22—C23 | −1.7 (3) |
P1—C14—C15—C16 | −176.92 (17) | C20—C21—C22—C23 | 176.08 (19) |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C33—C38, C2—C7, C8—C13 and C27—C32 rings, repectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cl2i | 0.95 | 2.85 | 3.532 (2) | 130 |
C26—H26···Cl2 | 0.95 | 2.72 | 3.555 (2) | 147 |
C29—H29···Cl1ii | 0.95 | 2.93 | 3.731 (2) | 143 |
C16—H16···Cg1ii | 0.95 | 2.73 | 3.443 (3) | 132 |
C23—H23···Cg2iii | 0.95 | 2.63 | 3.536 (2) | 159 |
C29—H29···Cg3ii | 0.95 | 2.99 | 3.525 (2) | 117 |
C36—H36···Cg4iv | 0.95 | 2.77 | 3.708 (3) | 169 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) −x, −y, −z+1; (iv) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [PtCl2(C19H17P)2] |
Mr | 818.58 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.5585 (12), 13.4135 (17), 14.7553 (18) |
α, β, γ (°) | 66.307 (2), 73.147 (3), 88.034 (3) |
V (Å3) | 1650.7 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 4.54 |
Crystal size (mm) | 0.24 × 0.1 × 0.08 |
Data collection | |
Diffractometer | Bruker APEX DUO 4K CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.409, 0.713 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33198, 8253, 7779 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.018, 0.039, 1.03 |
No. of reflections | 8253 |
No. of parameters | 388 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.65, −0.54 |
Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C33—C38, C2—C7, C8—C13 and C27—C32 rings, repectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cl2i | 0.95 | 2.85 | 3.532 (2) | 129.8 |
C26—H26···Cl2 | 0.95 | 2.72 | 3.555 (2) | 146.7 |
C29—H29···Cl1ii | 0.95 | 2.93 | 3.731 (2) | 142.5 |
C16—H16···Cg1ii | 0.95 | 2.73 | 3.443 (3) | 132 |
C23—H23···Cg2iii | 0.95 | 2.63 | 3.536 (2) | 159 |
C29—H29···Cg3ii | 0.95 | 2.99 | 3.525 (2) | 117 |
C36—H36···Cg4iv | 0.95 | 2.77 | 3.708 (3) | 169 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) −x, −y, −z+1; (iv) x−1, y, z. |
Acknowledgements
The Research Fund of the University of Johannesburg is gratefully acknowledged.
References
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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.
Transition metal complexes containing phosphine, arsine and stibine ligands are widely being investigated in various fields of organometallic chemistry (Spessard & Miessler, 1996). As part of a systematic investigation (Muller & Meijboom, 2010) involving complexes with the general formula trans/cis-[MX2(L)2] (M = Pt or Pd; X = halogen, Me, Ph; L = Group 15 donor ligand), crystals of the title compound were obtained by reaction of Zeize's salt, K[Pt(η2-ethylene)Cl3], with benzyldiphenylphosphane.
Molecules of the title compound (Fig. 1) crystallizes in the P1 (Z = 2) space group with the Pt atom lying on general positions in the unit cell. Each pair of equivalent ligands is in a mutually trans orientation with only slight distortion observed in the Pt square-planar coordination sphere (An averaged plane formed by the ligand donor atoms reveals that the Pt is displaced 0.1314 (3) Å from it; r.m.s. of fitted atoms = 0.0041 Å). The Pt—P1/P2 distances differ marginally (2.3096 (5) and 2.3155 (5) Å respectively), while the Pt—Cl distances deviates even less (2.3102 (5) and 2.3128 (5) Å respectively). The P—Pt—P and Cl—Pt—Cl angles show similar distortions from linearity (173.556 (18) and 173.220 (18)° respectively). The orientation of the phosphanes is such that they appear eclipsed when viewed along the P—M–P axis with one of the cyclohexcyl substituents from each phosphane almost perpendicular to the metal square-planar coordination plane (C—P—Pt—Cl dihedral angles vary from 83.74 (7) to 89.59 (7) °). To investigate the steric demand of the phosphane ligands their cone angles were calculated using an adaptation of the Tolman cone angle model (Tolman, 1977) where the geometry form the crystal structure determination is used and the metal phosphorus distance adjusted to 2.28 Å (Otto, 2001). Values obtained with this method vary from 160 to 169°. Surprisingly the cis isomer (Davis & Meijboom, 2011) of the title compound, where more crowding of the bulky ligands are expected, have slightly larger cone angle values (calculation results vary from 172 to 177°) which attest to the flexibility of this particular ligands' substituents. Comparing the title compound to structures from literature where the benzyldiphenylphosphane is coordinated to other transition metals, the cone angle values are comparable to the average cone angle value calculated. Data extracted from the Cambridge Structural Database shows an average cone angle of 165° for the phosphane from 27 hits, containing 43 useable observations, with a standard deviation of ±12° and a spread from 140° to 184°.
In the crystal structure several C—H···Cl interactions are observed (see table 1 and Fig. 2) linking molecules in infinite long chains along the [01–1] direction. Additional C—H···π interactions as well as π···π stacking are observed (centroid to centroid distance = 4.2499 (15) Å, ring slippage = 2.386 Å). These are summarized in Table 1 and Fig. 3.