(Biphenyl-2,2′-di­yl)[1,3-bis­(di­phenyl­phosphan­yl)propane-κ2P,P′]platinum(II)

Rillema, D.P.; Moore, C.; Jehan, A.

doi:10.1107/S2414314616012773

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 8| August 2016| x161277

doi:10.1107/S2414314616012773

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(Biphenyl-2,2′-diyl)[1,3-bis(diphenylphosphanyl)propane-κ²P,P′]platinum(II)

D. Paul Rillema,^a ^* Curtis Moore ^b and Ali Jehan ^a

^aDepartment of Chemistry, Wichita State University, Wichita, KS 67260, USA, and ^bCrystallographic Laboratory, University of California, San Diego, LaJolla, CA 92093, USA
^*Correspondence e-mail: paul.rillema@wichita.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 29 July 2016; accepted 8 August 2016; online 16 August 2016)

The C₂P₂ donor set in the title compound, [Pt(C₁₂H₈)(C₂₇H₂₆P₂)], defines a distorted planar coordination environment about the Pt^II atom with small deviations from planarity. The bidentate nature of the biphenyl dianionic ligand results in a C—Pt—C bond angle of 79.94 (16)° and a P—Pt—P bond angle of 93.40 (4)°. The average Pt—C bond length is 2.083 (3) Å [range 2.081 (4)–2.085 (4) Å]; the average Pt—P bond length is 2.308 (8) Å [range 2.3030 (11)–2.3136 (11) Å].

Keywords: crystal structure; platinum(II) biphenyl bis(diphenylphosphanyl)propane complex.

CCDC reference: 1498262

Structure description

We are interested in preparing Pt^II complexes containing the biphenyl dianion (bph²⁻) and bidentate ligands due to their excited state properties (Rillema et al., 2015 ) and determining their structures as a guide to design better photochromophores. The molecular structures of Pt(bph)(diimine) complexes revealed the bph²⁻ and the diimine ligands were not in the same plane as expected for square-planar Pt^II complexes, but were in an X or bowed configuration (Rillema et al., 2013a ,b ). Extensive π–π stacking was found for Pt(bph)(CO)₂ (Chen et al., 1995 ) but little π–π interaction is expected for the title compound (Fig. 1) due to its three-dimensional structure.

Figure 1
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

In the title compound, the C₂P₂ donor set approximates an isosceles trapezoid with a short distance defined by the C1—C2 distance of 2.676 (6) Å and the long distance defined by the P1—P2 distance of 3.360 (2) Å. The average length of the sides (C—P distance) is 3.198 (13) Å [range 3.188 (4)–3.207 (4) Å]. For the title compound, the average Pt—C bond length, the Pt—P bond length, the C—Pt—C bond angle and the P—Pt—P bond angle can be compared with a similar platinum(II) complex having a methyl group linking the two P atoms, viz. (2,2′-bi-o-phenylene-diyl)(bis(diphenylphosphanyl)methane)platinum(II) (DePriest et al., 2000 ) and a compound with two phenyl groups in place of the biphenyl dianionic ligand, viz. bis(4-bromo-2-dimethylaminophenyl)[1,3-bis(diphenylphosphanyl)propane-P:P]platinum(II), (Amijs et al., 2005 ). The average Pt—C bond lengths are similar for the series: 2.084 (3), 2.05 (1) and 2.065 (4) Å, respectively. The average Pt—P bond lengths in the series are also similar: 2.314 (4), 2.305 (8) and 2.2998 (11) Å, respectively. However, the C—Pt—C and P—Pt—P bond angles are markedly affected by removing the bond between the two phenyl rings of biphenyl and substituting methyl for the propyl linkage of the bidentate diphosphine ligand. Replacement of the propyl group with the methyl group results in an 20% decrease in the average P—Pt—P angle of 92 (3)° [range 93.40 (4) to 89.69 (6)°] to 73.10 (9)°. The C—Pt—C angle increases 10% from an average of 80.4 (7)° [range 79.94 (16) to 80.9 (4)°] to 89.69 (6)° after replacement of the bidentate biphenyl ligand with two phenyl groups. In the crystal packing, apart from van der Waals forces (Fig. 2), other noticeable intermolecular interactions are not present.

Figure 2
Packing diagram showing C—H⋯C interactions within van der Waals radii for H and C.

Synthesis and crystallization

The compound was synthesized according to previously published procedures (DePriest et al., 2000) with substitution of 1,3-bis(diphenylphosphanyl)propane for 1,1-bis(diphenylphosphanyl)methane. X-ray quality crystals were obtained by recrystallization from methylene chloride.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	[Pt(C₁₂H₈)(C₂₇H₂₆P₂)]
M_r	759.69
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	10.4487 (8), 16.8817 (13), 17.3829 (14)
V (Å³)	3066.2 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	4.71
Crystal size (mm)	0.16 × 0.14 × 0.13

Data collection
Diffractometer	Bruker X8 APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.061, 0.092
No. of measured, independent and observed [I > 2σ(I)] reflections	34318, 5614, 5472
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.016, 0.035, 1.04
No. of reflections	5614
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.32
Absolute structure	Flack x determined using 2339 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.015 (3)
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1498262

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616012773/wm4022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616012773/wm4022Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(Biphenyl-2,2'-diyl)[1,3-bis(diphenylphosphanyl)propane-κ²P,P']platinum(II) top

Crystal data top

[Pt(C₁₂H₈)(C₂₇H₂₆P₂)]	D_x = 1.646 Mg m⁻³
M_r = 759.69	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9939 reflections
a = 10.4487 (8) Å	θ = 2.3–25.4°
b = 16.8817 (13) Å	µ = 4.71 mm⁻¹
c = 17.3829 (14) Å	T = 100 K
V = 3066.2 (4) Å³	Block, yellow
Z = 4	0.16 × 0.14 × 0.13 mm
F(000) = 1504

Data collection top

Bruker X8 APEXII diffractometer	5614 independent reflections
Radiation source: sealed tube, fine-focus	5472 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 7.9 pixels mm^-1	θ_max = 25.4°, θ_min = 1.7°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −20→20
T_min = 0.061, T_max = 0.092	l = −20→20
34318 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.016	H-atom parameters constrained
wR(F²) = 0.035	w = 1/[σ²(F_o²) + (0.0167P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
5614 reflections	Δρ_max = 0.34 e Å⁻³
379 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 2339 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.015 (3)

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	0.43259 (2)	0.45678 (2)	0.59054 (2)	0.01281 (5)
P1	0.63061 (10)	0.50521 (7)	0.55401 (7)	0.0150 (2)
P2	0.32547 (10)	0.52666 (6)	0.49673 (6)	0.0147 (2)
C1	0.5101 (4)	0.3901 (2)	0.6801 (2)	0.0135 (9)
C2	0.2673 (4)	0.4035 (2)	0.6328 (2)	0.0142 (9)
C3	0.6388 (4)	0.3790 (3)	0.7007 (3)	0.0183 (10)
H3	0.7035	0.4000	0.6682	0.022*
C4	0.6753 (4)	0.3386 (2)	0.7667 (3)	0.0195 (10)
H4	0.7635	0.3331	0.7788	0.023*
C5	0.5839 (4)	0.3064 (2)	0.8146 (2)	0.0211 (10)
H5	0.6085	0.2801	0.8606	0.025*
C6	0.4554 (4)	0.3126 (2)	0.7949 (2)	0.0192 (10)
H6	0.3920	0.2894	0.8269	0.023*
C7	0.4185 (4)	0.3531 (2)	0.7278 (2)	0.0154 (9)
C8	0.2855 (4)	0.3584 (2)	0.7003 (2)	0.0152 (9)
C9	0.1838 (4)	0.3177 (3)	0.7346 (3)	0.0204 (10)
H9	0.1977	0.2892	0.7810	0.024*
C10	0.0630 (4)	0.3183 (2)	0.7018 (2)	0.0215 (10)
H10	−0.0054	0.2899	0.7250	0.026*
C11	0.0432 (4)	0.3609 (2)	0.6348 (3)	0.0193 (10)
H11	−0.0388	0.3609	0.6111	0.023*
C12	0.1438 (4)	0.4041 (2)	0.6018 (3)	0.0168 (10)
H12	0.1275	0.4347	0.5570	0.020*
C13	0.6409 (4)	0.5878 (3)	0.4846 (3)	0.0196 (11)
H13A	0.6266	0.6382	0.5124	0.024*
H13B	0.7286	0.5894	0.4630	0.024*
C14	0.5459 (4)	0.5826 (2)	0.4185 (3)	0.0212 (10)
H14A	0.5455	0.5280	0.3979	0.025*
H14B	0.5733	0.6187	0.3767	0.025*
C15	0.4107 (4)	0.6049 (2)	0.4443 (3)	0.0197 (10)
H15A	0.3600	0.6194	0.3983	0.024*
H15B	0.4160	0.6524	0.4776	0.024*
C16	0.7210 (4)	0.5468 (3)	0.6349 (2)	0.0174 (9)
C17	0.8461 (4)	0.5268 (2)	0.6541 (3)	0.0205 (10)
H17	0.8945	0.4937	0.6209	0.025*
C18	0.9004 (4)	0.5550 (3)	0.7215 (3)	0.0267 (11)
H18	0.9853	0.5403	0.7348	0.032*
C19	0.8315 (5)	0.6046 (3)	0.7697 (3)	0.0303 (12)
H19	0.8685	0.6234	0.8161	0.036*
C20	0.7076 (5)	0.6268 (3)	0.7495 (3)	0.0285 (11)
H20	0.6608	0.6623	0.7813	0.034*
C21	0.6528 (4)	0.5972 (3)	0.6831 (3)	0.0228 (11)
H21	0.5675	0.6115	0.6702	0.027*
C22	0.7279 (4)	0.4291 (2)	0.5079 (2)	0.0158 (9)
C23	0.8501 (4)	0.4447 (3)	0.4783 (2)	0.0191 (10)
H23	0.8851	0.4965	0.4826	0.023*
C24	0.9200 (4)	0.3860 (3)	0.4430 (2)	0.0217 (10)
H24	1.0030	0.3972	0.4235	0.026*
C25	0.8689 (4)	0.3100 (3)	0.4359 (3)	0.0238 (11)
H25	0.9180	0.2692	0.4125	0.029*
C26	0.7477 (4)	0.2938 (3)	0.4626 (2)	0.0209 (10)
H26	0.7118	0.2426	0.4561	0.025*
C27	0.6780 (4)	0.3534 (3)	0.4995 (2)	0.0188 (10)
H27	0.5952	0.3419	0.5191	0.023*
C28	0.2667 (3)	0.4647 (2)	0.4184 (2)	0.0153 (8)
C29	0.2077 (4)	0.4952 (3)	0.3526 (2)	0.0200 (10)
H29	0.1991	0.5509	0.3469	0.024*
C30	0.1613 (4)	0.4452 (3)	0.2954 (3)	0.0233 (10)
H30	0.1201	0.4666	0.2514	0.028*
C31	0.1753 (4)	0.3638 (3)	0.3030 (3)	0.0204 (10)
H31	0.1421	0.3294	0.2646	0.024*
C32	0.2375 (4)	0.3327 (3)	0.3663 (3)	0.0200 (10)
H32	0.2492	0.2771	0.3705	0.024*
C33	0.2832 (4)	0.3826 (2)	0.4239 (2)	0.0175 (10)
H33	0.3257	0.3608	0.4673	0.021*
C34	0.1939 (4)	0.5878 (2)	0.5334 (3)	0.0166 (9)
C35	0.2107 (4)	0.6179 (3)	0.6078 (2)	0.0198 (10)
H35	0.2825	0.6016	0.6374	0.024*
C36	0.1244 (4)	0.6710 (3)	0.6389 (3)	0.0248 (11)
H36	0.1372	0.6906	0.6895	0.030*
C37	0.0195 (4)	0.6956 (2)	0.5968 (3)	0.0212 (10)
H37	−0.0392	0.7325	0.6182	0.025*
C38	0.0006 (4)	0.6661 (3)	0.5233 (3)	0.0218 (11)
H38	−0.0715	0.6828	0.4943	0.026*
C39	0.0867 (4)	0.6121 (2)	0.4918 (3)	0.0193 (10)
H39	0.0724	0.5918	0.4416	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01280 (7)	0.01190 (7)	0.01373 (8)	0.00037 (7)	0.00056 (7)	0.00096 (7)
P1	0.0148 (5)	0.0130 (6)	0.0171 (6)	0.0004 (5)	0.0019 (5)	0.0000 (5)
P2	0.0162 (5)	0.0129 (6)	0.0149 (6)	0.0007 (4)	−0.0001 (4)	0.0010 (4)
C1	0.019 (2)	0.010 (2)	0.012 (2)	0.0009 (18)	−0.0017 (17)	−0.0028 (18)
C2	0.018 (2)	0.010 (2)	0.015 (2)	0.0009 (17)	0.0043 (18)	−0.0026 (18)
C3	0.021 (2)	0.013 (2)	0.021 (3)	0.0029 (19)	0.000 (2)	−0.002 (2)
C4	0.020 (2)	0.020 (2)	0.018 (3)	0.0003 (19)	−0.006 (2)	−0.002 (2)
C5	0.031 (3)	0.019 (2)	0.013 (2)	0.010 (2)	−0.006 (2)	−0.0004 (18)
C6	0.024 (3)	0.015 (2)	0.018 (2)	0.0020 (19)	0.0061 (19)	0.0006 (18)
C7	0.021 (2)	0.0110 (19)	0.014 (2)	0.0001 (19)	0.001 (2)	−0.0041 (17)
C8	0.019 (2)	0.010 (2)	0.017 (2)	0.0003 (18)	0.0025 (19)	−0.0021 (18)
C9	0.025 (2)	0.020 (2)	0.017 (2)	0.0038 (19)	0.007 (2)	0.004 (2)
C10	0.018 (2)	0.018 (2)	0.028 (3)	−0.001 (2)	0.007 (2)	0.0040 (19)
C11	0.012 (2)	0.016 (2)	0.030 (3)	0.0025 (18)	0.0025 (18)	0.000 (2)
C12	0.016 (2)	0.015 (2)	0.019 (3)	0.0033 (17)	−0.0005 (19)	0.003 (2)
C13	0.019 (2)	0.017 (2)	0.023 (3)	−0.0009 (19)	0.003 (2)	0.007 (2)
C14	0.024 (2)	0.019 (2)	0.021 (3)	0.0007 (18)	0.005 (2)	0.006 (2)
C15	0.022 (2)	0.017 (2)	0.020 (2)	−0.0008 (19)	−0.0014 (19)	0.0056 (18)
C16	0.019 (2)	0.013 (2)	0.020 (2)	−0.003 (2)	0.0027 (17)	0.002 (2)
C17	0.025 (2)	0.014 (3)	0.023 (3)	−0.0014 (19)	0.0022 (19)	−0.0012 (19)
C18	0.027 (2)	0.025 (3)	0.028 (3)	−0.008 (2)	−0.007 (2)	0.007 (2)
C19	0.049 (3)	0.022 (3)	0.019 (3)	−0.010 (2)	−0.008 (2)	−0.002 (2)
C20	0.042 (3)	0.023 (3)	0.021 (3)	−0.002 (2)	0.009 (2)	−0.003 (2)
C21	0.025 (2)	0.021 (3)	0.023 (3)	0.000 (2)	0.004 (2)	−0.004 (2)
C22	0.018 (2)	0.018 (2)	0.011 (2)	0.0044 (18)	−0.0027 (18)	0.0003 (18)
C23	0.023 (2)	0.018 (2)	0.017 (2)	−0.0049 (19)	−0.0002 (18)	−0.0005 (19)
C24	0.018 (2)	0.029 (3)	0.017 (2)	0.002 (2)	0.002 (2)	−0.0019 (19)
C25	0.027 (2)	0.026 (3)	0.019 (3)	0.012 (2)	−0.0025 (19)	−0.002 (2)
C26	0.029 (2)	0.016 (2)	0.017 (3)	0.004 (2)	−0.006 (2)	−0.0017 (19)
C27	0.022 (2)	0.020 (2)	0.015 (2)	−0.0008 (19)	−0.0013 (19)	0.0033 (19)
C28	0.0176 (18)	0.016 (2)	0.012 (2)	0.0003 (17)	0.0033 (16)	0.000 (2)
C29	0.027 (2)	0.016 (2)	0.018 (3)	0.002 (2)	0.001 (2)	−0.0005 (19)
C30	0.026 (2)	0.028 (3)	0.016 (2)	0.003 (2)	−0.0008 (18)	0.000 (2)
C31	0.023 (2)	0.021 (2)	0.017 (2)	0.002 (2)	0.0002 (19)	−0.006 (2)
C32	0.022 (2)	0.014 (2)	0.025 (3)	0.0009 (19)	0.002 (2)	−0.001 (2)
C33	0.018 (2)	0.021 (2)	0.015 (3)	0.0046 (18)	0.0026 (17)	0.0031 (19)
C34	0.018 (2)	0.013 (2)	0.019 (2)	−0.0028 (18)	0.0012 (19)	0.0040 (19)
C35	0.020 (2)	0.022 (2)	0.017 (3)	0.0032 (19)	−0.0039 (18)	−0.0029 (19)
C36	0.031 (3)	0.025 (3)	0.019 (3)	0.003 (2)	0.000 (2)	−0.005 (2)
C37	0.022 (2)	0.015 (2)	0.027 (3)	0.0048 (17)	0.005 (2)	0.000 (2)
C38	0.021 (2)	0.022 (3)	0.023 (3)	0.003 (2)	−0.002 (2)	0.006 (2)
C39	0.020 (2)	0.022 (2)	0.016 (2)	0.000 (2)	−0.0005 (19)	0.0032 (18)

Geometric parameters (Å, º) top

Pt1—P1	2.3136 (11)	C17—C18	1.386 (6)
Pt1—P2	2.3030 (11)	C18—H18	0.9500
Pt1—C1	2.085 (4)	C18—C19	1.386 (6)
Pt1—C2	2.081 (4)	C19—H19	0.9500
P1—C13	1.848 (4)	C19—C20	1.392 (7)
P1—C16	1.834 (4)	C20—H20	0.9500
P1—C22	1.824 (4)	C20—C21	1.382 (6)
P2—C15	1.836 (4)	C21—H21	0.9500
P2—C28	1.824 (4)	C22—C23	1.402 (6)
P2—C34	1.834 (4)	C22—C27	1.388 (6)
C1—C3	1.404 (5)	C23—H23	0.9500
C1—C7	1.412 (6)	C23—C24	1.375 (6)
C2—C8	1.411 (6)	C24—H24	0.9500
C2—C12	1.399 (5)	C24—C25	1.395 (6)
C3—H3	0.9500	C25—H25	0.9500
C3—C4	1.387 (6)	C25—C26	1.375 (6)
C4—H4	0.9500	C26—H26	0.9500
C4—C5	1.380 (6)	C26—C27	1.398 (6)
C5—H5	0.9500	C27—H27	0.9500
C5—C6	1.390 (6)	C28—C29	1.397 (6)
C6—H6	0.9500	C28—C33	1.400 (6)
C6—C7	1.405 (6)	C29—H29	0.9500
C7—C8	1.471 (6)	C29—C30	1.392 (6)
C8—C9	1.400 (6)	C30—H30	0.9500
C9—H9	0.9500	C30—C31	1.388 (6)
C9—C10	1.385 (6)	C31—H31	0.9500
C10—H10	0.9500	C31—C32	1.381 (6)
C10—C11	1.385 (6)	C32—H32	0.9500
C11—H11	0.9500	C32—C33	1.394 (6)
C11—C12	1.401 (6)	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.400 (6)
C13—H13A	0.9900	C34—C39	1.395 (6)
C13—H13B	0.9900	C35—H35	0.9500
C13—C14	1.520 (6)	C35—C36	1.381 (6)
C14—H14A	0.9900	C36—H36	0.9500
C14—H14B	0.9900	C36—C37	1.381 (6)
C14—C15	1.529 (6)	C37—H37	0.9500
C15—H15A	0.9900	C37—C38	1.386 (7)
C15—H15B	0.9900	C38—H38	0.9500
C16—C17	1.391 (6)	C38—C39	1.393 (6)
C16—C21	1.391 (6)	C39—H39	0.9500
C17—H17	0.9500

P2—Pt1—P1	93.40 (4)	C17—C16—P1	125.1 (3)
C1—Pt1—P1	92.76 (12)	C17—C16—C21	119.1 (4)
C1—Pt1—P2	173.79 (12)	C21—C16—P1	115.6 (3)
C2—Pt1—P1	172.62 (12)	C16—C17—H17	119.9
C2—Pt1—P2	93.91 (12)	C18—C17—C16	120.3 (4)
C2—Pt1—C1	79.94 (16)	C18—C17—H17	119.9
C13—P1—Pt1	119.88 (15)	C17—C18—H18	119.8
C16—P1—Pt1	112.65 (13)	C17—C18—C19	120.4 (4)
C16—P1—C13	100.5 (2)	C19—C18—H18	119.8
C22—P1—Pt1	111.73 (14)	C18—C19—H19	120.2
C22—P1—C13	102.2 (2)	C18—C19—C20	119.6 (4)
C22—P1—C16	108.64 (19)	C20—C19—H19	120.2
C15—P2—Pt1	118.98 (14)	C19—C20—H20	120.1
C28—P2—Pt1	113.49 (13)	C21—C20—C19	119.9 (4)
C28—P2—C15	101.83 (19)	C21—C20—H20	120.1
C28—P2—C34	109.30 (19)	C16—C21—H21	119.6
C34—P2—Pt1	113.99 (15)	C20—C21—C16	120.8 (4)
C34—P2—C15	97.55 (19)	C20—C21—H21	119.6
C3—C1—Pt1	129.4 (3)	C23—C22—P1	122.5 (3)
C3—C1—C7	116.1 (4)	C27—C22—P1	119.0 (3)
C7—C1—Pt1	114.4 (3)	C27—C22—C23	118.5 (4)
C8—C2—Pt1	114.5 (3)	C22—C23—H23	119.6
C12—C2—Pt1	128.8 (3)	C24—C23—C22	120.8 (4)
C12—C2—C8	116.6 (4)	C24—C23—H23	119.6
C1—C3—H3	118.7	C23—C24—H24	120.0
C4—C3—C1	122.7 (4)	C23—C24—C25	119.9 (4)
C4—C3—H3	118.7	C25—C24—H24	120.0
C3—C4—H4	119.9	C24—C25—H25	119.8
C5—C4—C3	120.2 (4)	C26—C25—C24	120.4 (4)
C5—C4—H4	119.9	C26—C25—H25	119.8
C4—C5—H5	120.3	C25—C26—H26	120.3
C4—C5—C6	119.3 (4)	C25—C26—C27	119.5 (4)
C6—C5—H5	120.3	C27—C26—H26	120.3
C5—C6—H6	119.8	C22—C27—C26	121.0 (4)
C5—C6—C7	120.4 (4)	C22—C27—H27	119.5
C7—C6—H6	119.8	C26—C27—H27	119.5
C1—C7—C8	115.0 (4)	C29—C28—P2	123.2 (3)
C6—C7—C1	121.1 (4)	C29—C28—C33	118.4 (4)
C6—C7—C8	123.9 (4)	C33—C28—P2	118.4 (3)
C2—C8—C7	115.5 (4)	C28—C29—H29	119.5
C9—C8—C2	121.1 (4)	C30—C29—C28	120.9 (4)
C9—C8—C7	123.3 (4)	C30—C29—H29	119.5
C8—C9—H9	119.6	C29—C30—H30	120.1
C10—C9—C8	120.9 (4)	C31—C30—C29	119.8 (4)
C10—C9—H9	119.6	C31—C30—H30	120.1
C9—C10—H10	120.4	C30—C31—H31	120.0
C9—C10—C11	119.1 (4)	C32—C31—C30	120.1 (4)
C11—C10—H10	120.4	C32—C31—H31	120.0
C10—C11—H11	119.9	C31—C32—H32	119.9
C10—C11—C12	120.1 (4)	C31—C32—C33	120.3 (4)
C12—C11—H11	119.9	C33—C32—H32	119.9
C2—C12—C11	122.1 (4)	C28—C33—H33	119.8
C2—C12—H12	118.9	C32—C33—C28	120.5 (4)
C11—C12—H12	118.9	C32—C33—H33	119.8
P1—C13—H13A	108.7	C35—C34—P2	115.6 (3)
P1—C13—H13B	108.7	C39—C34—P2	125.9 (3)
H13A—C13—H13B	107.6	C39—C34—C35	118.2 (4)
C14—C13—P1	114.3 (3)	C34—C35—H35	119.5
C14—C13—H13A	108.7	C36—C35—C34	121.0 (4)
C14—C13—H13B	108.7	C36—C35—H35	119.5
C13—C14—H14A	109.3	C35—C36—H36	119.8
C13—C14—H14B	109.3	C35—C36—C37	120.4 (4)
C13—C14—C15	111.6 (4)	C37—C36—H36	119.8
H14A—C14—H14B	108.0	C36—C37—H37	120.2
C15—C14—H14A	109.3	C36—C37—C38	119.5 (4)
C15—C14—H14B	109.3	C38—C37—H37	120.2
P2—C15—H15A	108.6	C37—C38—H38	119.8
P2—C15—H15B	108.6	C37—C38—C39	120.4 (4)
C14—C15—P2	114.6 (3)	C39—C38—H38	119.8
C14—C15—H15A	108.6	C34—C39—H39	119.8
C14—C15—H15B	108.6	C38—C39—C34	120.4 (4)
H15A—C15—H15B	107.6	C38—C39—H39	119.8

Acknowledgements

We are grateful for support from the National Science Foundation (EPSCoR), the Wichita State University Office of Research, and the Department of Energy..

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