Comparison of mol­ecular structures of cis-bis­[8-(di­methyl­phosphan­yl)quinoline]­nickel(II) and -platinum(II) complex cations

Mori, M.; Suzuki, T.

doi:10.1107/S2056989020014437

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Volume 76| Part 12| December 2020| Pages 1813-1817

https://doi.org/10.1107/S2056989020014437

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Comparison of molecular structures of cis-bis[8-(dimethylphosphanyl)quinoline]nickel(II) and -platinum(II) complex cations

Masatoshi Mori ^a and Takayoshi Suzuki ^b ^*

^aGraduate School of Natural Science and Technology, Okayama University, Okayama, 700-8530, Japan, and ^bResearch Institute for Interdisciplinary Science, Okayama University, Okayama, 700-8530, Japan
^*Correspondence e-mail: suzuki@okayama-u.ac.jp

Edited by S. Parkin, University of Kentucky, USA (Received 19 October 2020; accepted 29 October 2020; online 6 November 2020)

The crystal structures of the complexes (SP-4-2)-cis-bis[8-(dimethylphosphanyl)quinoline-κ²N,P]nickel(II) bis(perchlorate) nitromethane monosolvate, [Ni(C₁₁H₁₂NP)₂](ClO₄)₂·CH₃NO₂ (1), and (SP-4-2)-cis-bis[8-(dimethylphosphanyl)quinoline-κ²N,P]platinum(II) bis(tetrafluoroborate) acetonitrile monosolvate, [Pt(C₁₁H₁₂NP)₂](BF₄)₂·C₂H₃N (2), are reported. In both complex cations, two phosphanylquinolines act as bidentate P,N-donating chelate ligands and form the mutually cis configuration in the square-planar coordination geometry. The strong trans influence of the dimethylphosphanyl donor group is confirmed by the Ni—N bond lengths in 1, 1.970 (2) and 1.982 (2) Å and, the Pt—N bond lengths of 2, 2.123 (4) and 2.132 (4) Å, which are relatively long as compared to those in the analogous 8-(diphenylphosphanyl)quinoline complexes. Mutually cis-positioned quinoline donor groups would give a severe steric hindrance between their ortho-H atoms. In order to reduce such a steric congestion, the Ni^II complex in 1 shows a tetrahedral distortion of the coordination geometry, as parameterized by τ₄ = 0.199 (1)°, while the Pt^II complex in 2 exhibits a typical square-planar coordination geometry [τ₄ = 0.014 (1)°] with a large bending deformation of the ideally planar Me₂Pqn chelate planes. In the crystal structure of 2, three F atoms of one of the BF₄⁻ anions are disordered over two sets of positions with refined occupancies of 0.573 (10) and 0.427 (10).

Keywords: 8-quinolylphosphane; asymmetrical bidentate ligand; square-planar coordination; tetrahedral distortion; trans influence; crystal structure.

CCDC references: 2041421; 2041420

1. Chemical context

8-Quinolylphosphanes are an intriguing class of ligands because they form a planar asymmetrical five-membered chelate ring via coordination through a phosphane-P atom having a strong σ-donating character and an imine-N atom incorporated in a π-conjugated quinoline ring (Salem & Wild, 1992 ; Scattolin et al., 2017 ; Cai et al., 2018 ). The electronic properties of these ligands, in particular their π-bonding nature, may stabilize unusual electronic states of their transition-metal complexes (Suzuki et al., 1995 ; Hashimoto et al., 2010 ; Hopkins et al., 2019 ). In addition, the steric requirement from the planar quinoline moiety often has a significant influence on the properties of their metal complexes. For example, the nickel(II), palladium(II) and platinum(II) complexes containing two 8-(diphenylphosphanyl)quinoline (Ph₂Pqn) in the cis(P,P) configuration exhibit a severe distortion of the square-planar coordination geometry around M^II (M = Ni, Pd or Pt; Suzuki, 2004 ; Hashimoto et al., 2010; Mori et al., 2020 ). The dimethylphosphanyl analogue, 8-(dimethylphosphanyl)quinoline (Me₂Pqn), is an interesting derivative, because it would give a stronger trans influence, which could affect the steric congestion between the intramolecular ligands. However, the transition-metal complexes bearing Me₂Pqn are limited to only those listed in section 4: Database survey, all of which were reported by our group. In 1995 we reported the preparation and crystal structure of (SP-4-2)-[Pd(Me₂Pqn)₂](BF₄)₂ (Suzuki et al., 1995), but the crystal structures of the corresponding Ni^II and Pt^II complexes were not compared.

2. Structural commentary

A red block-shaped crystal of the Ni^II complex, [Ni(Me₂Pqn)₂](ClO₄)₂·CH₃NO₂ (1), recrystallized from nitromethane/diisopropyl ether and a colorless platelet crystal of the Pt^II complex, [Pt(Me₂Pqn)₂](BF₄)₂·CH₃CN (2), recrystallized from acetonitrile/diisopropyl ether were used for the X-ray diffraction analysis.

In the crystal structure of 2, three F atoms of one of the BF₄⁻ anions show disorder over two sets of positions: (F2A, F3A and F4A) and (F2B, F3B and F4B). The occupancy parameters of these atoms were refined with suitable restrictions and found to be 0.573 (10) and 0.427 (10) for the A-set atoms and the B-set atoms, respectively.

In both crystals, two Me₂Pqn ligands coordinate to a metal(II) center in the bidentate κ²P,N mode to form a cis-isomer of the complex dication, (SP-4-2)-[M(Me₂Pqn)₂]²⁺ (M = Ni or Pt), having a roughly square-planar coordination geometry (Figs. 1 and 2, Tables 1 and 2). For the group 10 metal(II) complexes bearing 8-quinolylphosphanes, it was revealed that most of the bis(κ²P,N)-type complexes have a similar geometrical structure, except for those of the halide complexes (Suzuki, 2004; Mori et al., 2020), because the strong trans influence of the phosphane donor groups makes the mutually trans(P,P) configuration thermodynamically unstable. The Ni—N bond lengths in 1 are 1.970 (2) and 1.982 (2) Å, which are slightly longer than those in [Ni(MePhPqn)₂](BF₄)₂ [MePhPqn = 8-(methylphenylphosphanyl)quinoline; 1.954 (3) and 1.977 (3) Å] and [Ni(Ph₂Pqn)₂](BF₄)₂ [1.954 (6) and 1.949 (5) Å] (Hashimoto et al., 2010), indicating the trans influence becomes stronger in the order of Ph₂Pqn < MePhPqn < Me₂Pqn. In the case of Pt^II complexes, the Pt—N bond lengths in 2 [2.123 (4) and 2.132 (4) Å] are similarly long, as compared to those in [Pt(Ph₂Pqn)₂](ClO₄)₂ [2.107 (4) and 2.108 (5) Å; Mori et al., 2020]. By contrast, the Ni—P bond lengths and the P—Ni—N chelate bite angles are comparable among the complexes 1 [2.1576 (7) and 2.1534 (7) Å; 86.13 (7) and 85.97 (6)°], [Ni(MePhPqn)₂](BF₄)₂ [2.151 (1) and 2.162 (1) Å; 87.4 (1) and 86.6 (1)°] and [Ni(Ph₂Pqn)₂](BF₄)₂ [2.168 (2) and 2.177 (2) Å; 86.6 (1) and 84.6 (1)°]. The Pt—P bond lengths and the P—Pt—N bite angles in 2 [2.2293 (12) and 2.2365 (12) Å; 82.76 (11) and 81.93 (11)°] are also comparable to those in [Pt(Ph₂Pqn)₂](ClO₄)₂ [2.2311 (14) and 2.2318 (14) Å; 83.29 (13) and 82.79 (13)°].

Table 1
Selected geometric parameters (Å, °) for 1

Ni1—N1	1.970 (2)	Ni1—P2	2.1534 (7)
Ni1—N2	1.982 (2)	Ni1—P1	2.1576 (7)

N1—Ni1—N2	97.01 (9)	N1—Ni1—P1	86.13 (7)
N1—Ni1—P2	166.27 (7)	N2—Ni1—P1	165.68 (6)
N2—Ni1—P2	85.97 (6)	P2—Ni1—P1	94.29 (3)

Ni1—P1—C8—C9	14.54 (19)	Ni1—P2—C19—C20	18.86 (19)
Ni1—N1—C9—C8	−11.8 (3)	Ni1—N2—C20—C19	−9.7 (3)

Table 2
Selected geometric parameters (Å, °) for 2

Pt1—N1	2.123 (4)	Pt1—P2	2.2293 (12)
Pt1—N2	2.132 (4)	Pt1—P1	2.2365 (12)

N1—Pt1—N2	97.13 (15)	N1—Pt1—P1	82.76 (11)
N1—Pt1—P2	178.51 (11)	N2—Pt1—P1	179.55 (11)
N2—Pt1—P2	81.93 (11)	P2—Pt1—P1	98.17 (4)

Pt1—P1—C8—C9	15.5 (3)	Pt1—P2—C19—C20	21.2 (4)
Pt1—N1—C9—C8	−18.9 (5)	Pt1—N2—C20—C19	−19.0 (5)

Figure 1
An ellipsoid plot of the molecular structures in [Ni(Me₂Pqn)₂](ClO₄)₂·CH₃NO₂ (1), showing the atom-numbering scheme, with ellipsoids drawn at the 50% probability level.

Figure 2
An ellipsoid plot of the molecular structures in [Pt(Me₂Pqn)₂](BF₄)₂·CH₃CN (2), showing the atom-numbering scheme, with ellipsoids drawn at the 50% probability level. The minor component atoms (F2B, F3B and F4B) of the positionally disordered F atoms are omitted for clarity.

Comparison of the Ni^II complex cation in 1 and the corresponding Pt^II complex cation in 2 shows an obvious difference in their coordination geometry (Figs. 3 and 4). The four-coordinate Ni^II center in 1 exhibits a large tetrahedral distortion, as indicated by the τ₄ value (Yang et al., 2007 ) of 0.199 (1)°. This is due to the steric requirement from the planar quinoline moiety located in the mutually cis positions around the Ni^II center. In the analogous MePhPqn and Ph₂Pqn complexes, the τ₄ values are 0.273 (1)° and 0.189 (2)°, respectively. By contrast, the τ₄ value of the Pt^II complex in 2 is only 0.014 (1)°, indicating a nearly perfect planar coordination geometry around the Pt^II center. The corresponding value in [Pt(Ph₂Pqn)₂](BF₄)₂ is 0.149 (2)° (Mori et al., 2020). It is obvious that the present planar structure of the Pt^II center in 2 is a rare example. In this complex, the interligand steric interaction expected for the mutually cis-positioned quinoline groups could be reduced by envelope-type bending of the planar Me₂Pqn chelate coordination, that is, the displacement of the Pt^II metal center from the ideal plane defined by the chelate ring of 8-quinolylphosphanes. The dihedral angle, φ_C, between the [Pt,P,N] coordination plane and the [PCCN] phosphanylquinoline planes in 2 are 21.53 (16) and 24.76 (16)°, and the displacement of the Pt1 atom from the ideal quinoline [C₉H₆N] planes is 0.579 (5) and 0.550 (5) Å. The two quinoline planes are nearly parallel, with the dihedral angle between them being only 7.99 (10)°. Such a synchronized bending deformation of two chelate coordination (Fig. 4) acts to reduce the steric congestion effectively. The corresponding φ_C values for 1 are 17.44 (9) and 19.76 (9)°, and the dihedral angle between the two quinoline planes is obviously large, at 33.35 (6)°. Interestingly, the analogous palladium(II) complex, [Pd(Me₂Pqn)₂](BF₄)₂, has a τ₄ value of 0.096 (2)° (Suzuki et al., 1995), which is in between those of the present Ni^II and Pt^II complexes.

Figure 3
A perspective side view (from one of the NiPN coordination planes) of [Ni(Me₂Pqn)₂](ClO₄)₂·CH₃NO₂ (1). Color code: Ni, dark green; P, orange; N, blue; C, black and H, gray.

Figure 4
A perspective side view (from one of the PtPN coordination planes) of [Pt(Me₂Pqn)₂](BF₄)₂·CH₃CN (2). Color code: Pt, purple; P, orange; N, blue; C, black and H, gray.

3. Supramolecular features

In the crystal structure of 1, there are two ClO₄⁻ anions and a CH₃NO₂ solvent molecule, in addition to the [Ni(Me₂Pqn)₂]²⁺ complex cation in the asymmetric unit. The asymmetric unit of the Pt^II complex, 2, contains a [Pt(Me₂Pqn)₂]²⁺ complex cation, two BF₄⁻ anions (in one of which the positions of three F atoms are disordered) and a CH₃CN solvent molecule. In the crystal structures of both 1 and 2 (Figs. 5 and 6, respectively), no remarkable intermolecular stacking or hydrogen-bonding interactions are observed.

Figure 5
A packing drawing of [Ni(Me₂Pqn)₂](ClO₄)₂CH₃NO₂ (1) along the crystallographic b axis (two unit cells are shown). Color code: Ni, dark green; Cl, light green; P, orange; O, red; N, blue; C, black and H, gray.

Figure 6
A packing drawing of [Pt(Me₂Pqn)₂](BF₄)₂·CH₃CN (2) along the crystallographic a axis (two unit cells are shown). Color code: Pt, purple; P, orange; F, green; N, blue; C, black; B, pale purple and H, gray.

4. Database survey

Metal complexes containing Me₂Pqn have been reported by us, e.g., cis-[Pd(Me₂Pqn)₂](BF₄)₂ (refcode ZIFPUZ in the CSD database, version 5.41, last update May 2020; Groom et al., 2016 ) and [Pd₂Cl₂(Me₂Pqn)₂] (ZIFQAG; Suzuki et al., 1995), [Cu(Me₂Pqn)₂]PF₆ (OZILAL; Suzuki et al., 2011 ), [Ru(bpy)_3–n(Me₂Pqn)_n](PF₆)₂ (bpy = 2,2′-bipyridine; HUTRIV, HUTPCB, HUTPUH and HUTQAO; Suzuki et al., 2003 ), and [Pt(ppy)(Me₂Pqn)]BF₄ (ppy = 2-(2′-pyridyl)phenyl; Mori & Suzuki, 2020 ). Some of the related bis(8-quinolylphosphanes) complexes are: [Ni(Ph₂Pqn)₂](BF₄)_n (n = 1 or 2; BUGDAJ, BUGDEN and BUGDOX) and [Ni(MePhPqn)₂](BF₄)₂ (BUGDIR; Hashimoto et al., 2010), [Pd(Ph₂Pqn)₂]X₂ (X₂ = Cl₂, Br₂ or ClBF₄; FERZOS, FERZUY and FESBAH; Suzuki, 2004), [Cu(Ph₂Pqn)₂]BF₄ (OZILEP and OZILEP01; Suzuki et al., 2011) and [Cu(Ph₂Pqn)₂]PF₆ (NOPNIQ; Tsukuda et al., 2009 ).

5. Synthesis and crystallization

The ligand, Me₂Pqn, and the nickel(II) complexes, [Ni(Me₂Pqn)₂](ClO₄)₂, were prepared according to the method reported previously (Suzuki et al., 1995). Single crystals of 1 suitable for an X-ray diffraction study were obtained by recrystallization from nitromethane by diffusion of diisopropyl ether. The platinum(II) complex, [Pt(Me₂Pqn)₂](BF₄)₂, was prepared by the following method. A methanol (5 ml) solution of Me₂Pqn (0.76 mmol) was added dropwise with stirring to a dichloromethane solution (10 ml) of [PtCl₂(EtCN)₂] (0.105 g, 0.278 mmol), and the mixture was stirred for 24 h at room temperature. After removal of the resulting precipitate, the filtrate was concentrated to ca 5 ml using a rotary evaporator. A large excess amount of a methanol solution of NaBF₄ was added, and the mixture was stirred for 1 h at room temperature. The resulting pale-yellow precipitate was collected by filtration, washed with water (5 ml) and diethyl ether (10 ml), and dried in vacuo. Colorless platelet-shaped crystals of [Pt(Me₂Pqn)₂](BF₄)₂·CH₃CN (2) were obtained by recrystallization from an acetonitrile solution by diffusion of diisopropyl ether. Yield: 0.126 g (61%). Analysis calculated for C₂₄H₂₇B₂F₈N₃P₂Pt: C, 35.37; H, 3.24; N, 3.75%. Found (after completely drying): C, 35.39; H, 2.89; N, 3.74%.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were refined using a riding model, with C—H = 0.95 (aromatic) or 0.98 (methyl) Å and U_iso(H) = 1.2U_eq(C). In the analysis of 2, two sets of F atoms for one of the two BF₄⁻ anions were introduced as positionally disordered atoms, and their occupation parameters were refined with suitable restrictions [the final major:minor occupancy ratio was 0.573 (10):0.427 (10)].

Table 3
Experimental details

	1	2
Crystal data
Chemical formula	[Ni(C₁₁H₁₂NP)₂](ClO₄)₂·CH₃NO₂	[Pt(C₁₁H₁₂NP)₂](BF₄)₂·C₂H₃N
M_r	697.02	788.13
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/n
Temperature (K)	188	188
a, b, c (Å)	17.8114 (13), 8.9398 (6), 18.0245 (14)	7.9102 (3), 21.0833 (5), 16.7519 (4)
β (°)	100.524 (3)	95.3931 (11)
V (Å³)	2821.8 (4)	2781.42 (15)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	1.05	5.23
Crystal size (mm)	0.70 × 0.50 × 0.20	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995 )	Numerical (NUMABS; Rigaku, 1999 )
T_min, T_max	0.379, 0.811	0.338, 0.594
No. of measured, independent and observed [I > 2σ(I)] reflections	26671, 6459, 5440	43967, 6350, 5435
R_int	0.041	0.042
(sin θ/λ)_max (Å⁻¹)	0.649	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.117, 1.05	0.033, 0.084, 1.07
No. of reflections	6459	6350
No. of parameters	370	366
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.49	1.42, −1.45
Computer programs: RAPID AUTO (Rigaku, 1998 ), CrystalStructure (Rigaku, 2010 ), SIR2011 (Burla et al., 2012 ), SHELXL2013 (Sheldrick, 2015 ) and CrystalMaker (CrystalMaker Software, 2017 ).

Supporting information

CCDC references: 2041421; 2041420

Crystal structure: contains datablocks 1, 2, global. DOI: https://doi.org/10.1107/S2056989020014437/pk2650sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989020014437/pk26501sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989020014437/pk26502sup3.hkl

checkCIF report

Computing details top

For both structures, data collection: RAPID AUTO (Rigaku, 1998); cell refinement: RAPID AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku, 2010); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: CrystalMaker (CrystalMaker Software, 2017); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

(SP-4-2)-cis-Bis[8-(dimethylphosphanyl)quinoline-κ²N,P]nickel(II) bis(perchlorate) nitromethane monosolvate (1) top

Crystal data top

[Ni(C₁₁H₁₂NP)₂](ClO₄)₂·CH₃NO₂	F(000) = 1432
M_r = 697.02	D_x = 1.641 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
a = 17.8114 (13) Å	Cell parameters from 20058 reflections
b = 8.9398 (6) Å	θ = 3.2–27.6°
c = 18.0245 (14) Å	µ = 1.05 mm⁻¹
β = 100.524 (3)°	T = 188 K
V = 2821.8 (4) Å³	Block, red
Z = 4	0.70 × 0.50 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	6459 independent reflections
Radiation source: fine-focus sealed tube	5440 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.041
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −23→23
T_min = 0.379, T_max = 0.811	k = −11→10
26671 measured reflections	l = −23→23

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0596P)² + 2.7492P] where P = (F_o² + 2F_c²)/3
6459 reflections	(Δ/σ)_max = 0.001
370 parameters	Δρ_max = 1.03 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻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
Ni1	0.74556 (2)	0.21692 (3)	0.05020 (2)	0.02369 (10)
Cl1	0.60962 (3)	0.03126 (7)	−0.11398 (3)	0.02893 (15)
Cl2	0.90376 (4)	0.47701 (8)	0.15809 (4)	0.03678 (16)
P1	0.79934 (4)	0.00551 (7)	0.08449 (4)	0.02582 (15)
P2	0.68019 (4)	0.22150 (7)	0.13957 (3)	0.02357 (14)
O1	0.57753 (13)	0.1576 (2)	−0.15803 (13)	0.0477 (5)
O2	0.59943 (13)	−0.1010 (2)	−0.15961 (11)	0.0409 (5)
O3	0.57362 (13)	0.0136 (3)	−0.04995 (12)	0.0495 (6)
O4	0.68979 (11)	0.0582 (3)	−0.08854 (13)	0.0475 (5)
O5	0.94703 (18)	0.4498 (6)	0.1033 (2)	0.1249 (18)
O6	0.9264 (2)	0.6110 (4)	0.1969 (2)	0.1026 (13)
O7	0.9117 (3)	0.3654 (5)	0.2115 (3)	0.156 (2)
O8	0.82342 (15)	0.4791 (4)	0.12503 (17)	0.0726 (8)
O9	0.77720 (18)	0.6729 (4)	−0.1337 (2)	0.1098 (15)
O10	0.70736 (19)	0.6516 (3)	−0.24168 (17)	0.0800 (10)
N1	0.82335 (12)	0.2389 (2)	−0.01392 (12)	0.0267 (4)
N2	0.67687 (12)	0.3788 (2)	0.00323 (11)	0.0251 (4)
N3	0.75088 (15)	0.7214 (3)	−0.19493 (17)	0.0435 (6)
C1	0.83949 (15)	0.3680 (3)	−0.04390 (15)	0.0334 (6)
H1	0.8160	0.4564	−0.0300	0.040*
C2	0.88960 (16)	0.3797 (4)	−0.09511 (16)	0.0408 (7)
H2	0.9004	0.4747	−0.1144	0.049*
C3	0.92279 (16)	0.2540 (4)	−0.11705 (16)	0.0408 (7)
H3	0.9538	0.2594	−0.1546	0.049*
C4	0.91060 (14)	0.1157 (4)	−0.08344 (15)	0.0349 (6)
C5	0.94656 (15)	−0.0205 (4)	−0.09839 (17)	0.0413 (7)
H5	0.9771	−0.0228	−0.1364	0.050*
C6	0.93793 (16)	−0.1476 (4)	−0.05907 (18)	0.0429 (7)
H6	0.9621	−0.2375	−0.0702	0.051*
C7	0.89332 (15)	−0.1466 (3)	−0.00189 (17)	0.0364 (6)
H7	0.8894	−0.2343	0.0270	0.044*
C8	0.85549 (14)	−0.0183 (3)	0.01185 (15)	0.0286 (5)
C9	0.86259 (13)	0.1132 (3)	−0.02987 (14)	0.0277 (5)
C10	0.86537 (16)	−0.0119 (3)	0.17317 (16)	0.0370 (6)
H10A	0.9035	0.0681	0.1772	0.044*
H10B	0.8910	−0.1092	0.1753	0.044*
H10C	0.8373	−0.0040	0.2150	0.044*
C11	0.73838 (16)	−0.1577 (3)	0.07758 (19)	0.0391 (6)
H11A	0.7694	−0.2480	0.0768	0.047*
H11B	0.7002	−0.1523	0.0311	0.047*
H11C	0.7126	−0.1611	0.1212	0.047*
C12	0.66794 (15)	0.4179 (3)	−0.06857 (14)	0.0298 (5)
H12	0.6936	0.3612	−0.1009	0.036*
C13	0.62244 (16)	0.5391 (3)	−0.09962 (16)	0.0354 (6)
H13	0.6166	0.5605	−0.1520	0.042*
C14	0.58701 (15)	0.6251 (3)	−0.05472 (16)	0.0349 (6)
H14	0.5590	0.7111	−0.0745	0.042*
C15	0.59216 (14)	0.5853 (3)	0.02189 (15)	0.0287 (5)
C16	0.55524 (15)	0.6643 (3)	0.07288 (17)	0.0343 (6)
H16	0.5277	0.7531	0.0569	0.041*
C17	0.55876 (15)	0.6142 (3)	0.14475 (17)	0.0357 (6)
H17	0.5353	0.6702	0.1791	0.043*
C18	0.59706 (15)	0.4793 (3)	0.16850 (16)	0.0320 (6)
H18	0.5962	0.4416	0.2176	0.038*
C19	0.63542 (14)	0.4026 (3)	0.12141 (14)	0.0262 (5)
C20	0.63564 (14)	0.4568 (3)	0.04816 (14)	0.0250 (5)
C21	0.60140 (15)	0.0941 (3)	0.13956 (17)	0.0348 (6)
H21A	0.5720	0.0851	0.0882	0.042*
H21B	0.5683	0.1325	0.1731	0.042*
H21C	0.6212	−0.0044	0.1573	0.042*
C22	0.73083 (16)	0.2268 (3)	0.23602 (14)	0.0332 (6)
H22A	0.6946	0.2457	0.2698	0.040*
H22B	0.7690	0.3069	0.2416	0.040*
H22C	0.7563	0.1306	0.2489	0.040*
C23	0.77162 (18)	0.8734 (3)	−0.21331 (18)	0.0415 (7)
H23A	0.7415	0.9028	−0.2622	0.050*
H23B	0.8261	0.8769	−0.2158	0.050*
H23C	0.7611	0.9425	−0.1742	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02478 (17)	0.02146 (17)	0.02684 (18)	0.00232 (12)	0.00998 (12)	0.00229 (11)
Cl1	0.0286 (3)	0.0280 (3)	0.0311 (3)	0.0003 (2)	0.0078 (2)	−0.0003 (2)
Cl2	0.0402 (4)	0.0324 (3)	0.0390 (4)	−0.0014 (3)	0.0107 (3)	−0.0005 (3)
P1	0.0232 (3)	0.0227 (3)	0.0327 (3)	0.0020 (2)	0.0082 (2)	0.0015 (2)
P2	0.0240 (3)	0.0233 (3)	0.0246 (3)	0.0029 (2)	0.0078 (2)	0.0016 (2)
O1	0.0566 (13)	0.0350 (11)	0.0505 (13)	0.0162 (10)	0.0072 (11)	0.0061 (9)
O2	0.0594 (13)	0.0287 (10)	0.0360 (11)	−0.0060 (9)	0.0123 (10)	−0.0034 (8)
O3	0.0531 (13)	0.0633 (15)	0.0376 (12)	−0.0076 (11)	0.0227 (10)	−0.0053 (10)
O4	0.0267 (10)	0.0517 (13)	0.0637 (14)	−0.0025 (9)	0.0070 (9)	−0.0069 (11)
O5	0.0573 (18)	0.220 (5)	0.107 (3)	−0.033 (2)	0.0413 (19)	−0.094 (3)
O6	0.091 (2)	0.082 (2)	0.149 (3)	−0.041 (2)	0.059 (2)	−0.062 (2)
O7	0.164 (4)	0.120 (4)	0.159 (4)	−0.038 (3)	−0.041 (3)	0.091 (3)
O8	0.0430 (14)	0.095 (2)	0.080 (2)	0.0072 (14)	0.0111 (13)	−0.0257 (16)
O9	0.070 (2)	0.103 (3)	0.139 (3)	−0.0263 (18)	−0.029 (2)	0.086 (2)
O10	0.110 (2)	0.0643 (17)	0.0767 (19)	−0.0462 (18)	0.0471 (18)	−0.0385 (15)
N1	0.0243 (10)	0.0289 (10)	0.0280 (11)	−0.0045 (9)	0.0071 (8)	−0.0013 (8)
N2	0.0278 (10)	0.0213 (10)	0.0271 (10)	−0.0013 (8)	0.0074 (8)	0.0013 (8)
N3	0.0373 (13)	0.0317 (13)	0.0643 (18)	0.0005 (11)	0.0165 (13)	0.0012 (12)
C1	0.0315 (13)	0.0354 (14)	0.0337 (14)	−0.0072 (11)	0.0073 (11)	0.0006 (11)
C2	0.0332 (14)	0.0522 (18)	0.0378 (15)	−0.0148 (13)	0.0088 (12)	0.0072 (13)
C3	0.0261 (13)	0.066 (2)	0.0326 (14)	−0.0110 (14)	0.0113 (11)	−0.0016 (14)
C4	0.0211 (11)	0.0549 (18)	0.0286 (13)	−0.0042 (12)	0.0043 (10)	−0.0086 (12)
C5	0.0213 (12)	0.066 (2)	0.0377 (15)	0.0004 (13)	0.0072 (11)	−0.0178 (14)
C6	0.0263 (13)	0.0550 (19)	0.0467 (17)	0.0075 (13)	0.0051 (12)	−0.0227 (15)
C7	0.0275 (13)	0.0372 (15)	0.0432 (16)	0.0036 (12)	0.0026 (11)	−0.0096 (12)
C8	0.0204 (11)	0.0324 (13)	0.0328 (13)	−0.0007 (10)	0.0044 (10)	−0.0071 (10)
C9	0.0205 (11)	0.0343 (13)	0.0282 (12)	−0.0036 (10)	0.0038 (9)	−0.0080 (10)
C10	0.0324 (14)	0.0433 (16)	0.0354 (15)	0.0106 (12)	0.0069 (11)	0.0035 (12)
C11	0.0338 (14)	0.0282 (13)	0.0570 (18)	−0.0022 (12)	0.0128 (13)	0.0031 (13)
C12	0.0320 (13)	0.0285 (12)	0.0295 (13)	−0.0043 (11)	0.0068 (10)	0.0019 (10)
C13	0.0365 (14)	0.0350 (14)	0.0332 (14)	−0.0058 (12)	0.0023 (11)	0.0129 (11)
C14	0.0321 (13)	0.0256 (13)	0.0450 (16)	−0.0024 (11)	0.0014 (12)	0.0106 (11)
C15	0.0244 (11)	0.0212 (11)	0.0394 (14)	−0.0027 (10)	0.0029 (10)	0.0006 (10)
C16	0.0273 (12)	0.0226 (12)	0.0517 (17)	0.0033 (10)	0.0035 (12)	−0.0029 (11)
C17	0.0292 (13)	0.0324 (14)	0.0457 (16)	0.0073 (11)	0.0075 (11)	−0.0120 (12)
C18	0.0288 (12)	0.0345 (14)	0.0330 (14)	0.0043 (11)	0.0065 (10)	−0.0053 (11)
C19	0.0247 (11)	0.0256 (12)	0.0279 (12)	0.0022 (10)	0.0039 (9)	−0.0016 (9)
C20	0.0239 (11)	0.0199 (11)	0.0309 (12)	−0.0014 (9)	0.0043 (9)	−0.0015 (9)
C21	0.0294 (13)	0.0337 (14)	0.0436 (15)	−0.0020 (11)	0.0128 (11)	0.0019 (12)
C22	0.0383 (14)	0.0352 (14)	0.0256 (13)	0.0099 (12)	0.0047 (11)	0.0011 (10)
C23	0.0407 (15)	0.0336 (15)	0.0501 (17)	−0.0029 (13)	0.0081 (13)	0.0051 (13)

Geometric parameters (Å, º) top

Ni1—N1	1.970 (2)	C6—C7	1.412 (4)
Ni1—N2	1.982 (2)	C6—H6	0.9500
Ni1—P2	2.1534 (7)	C7—C8	1.376 (4)
Ni1—P1	2.1576 (7)	C7—H7	0.9500
Cl1—O3	1.428 (2)	C8—C9	1.413 (4)
Cl1—O2	1.433 (2)	C10—H10A	0.9800
Cl1—O1	1.438 (2)	C10—H10B	0.9800
Cl1—O4	1.438 (2)	C10—H10C	0.9800
Cl2—O7	1.376 (4)	C11—H11A	0.9800
Cl2—O5	1.381 (3)	C11—H11B	0.9800
Cl2—O6	1.408 (3)	C11—H11C	0.9800
Cl2—O8	1.446 (3)	C12—C13	1.406 (4)
P1—C8	1.800 (3)	C12—H12	0.9500
P1—C11	1.809 (3)	C13—C14	1.353 (4)
P1—C10	1.810 (3)	C13—H13	0.9500
P2—C22	1.807 (3)	C14—C15	1.413 (4)
P2—C21	1.807 (3)	C14—H14	0.9500
P2—C19	1.808 (3)	C15—C16	1.413 (4)
O9—N3	1.199 (4)	C15—C20	1.417 (3)
O10—N3	1.209 (4)	C16—C17	1.361 (4)
N1—C1	1.327 (3)	C16—H16	0.9500
N1—C9	1.381 (3)	C17—C18	1.413 (4)
N2—C12	1.322 (3)	C17—H17	0.9500
N2—C20	1.378 (3)	C18—C19	1.367 (3)
N3—C23	1.462 (4)	C18—H18	0.9500
C1—C2	1.400 (4)	C19—C20	1.407 (3)
C1—H1	0.9500	C21—H21A	0.9800
C2—C3	1.362 (5)	C21—H21B	0.9800
C2—H2	0.9500	C21—H21C	0.9800
C3—C4	1.411 (4)	C22—H22A	0.9800
C3—H3	0.9500	C22—H22B	0.9800
C4—C9	1.402 (3)	C22—H22C	0.9800
C4—C5	1.424 (4)	C23—H23A	0.9800
C5—C6	1.363 (5)	C23—H23B	0.9800
C5—H5	0.9500	C23—H23C	0.9800

N1—Ni1—N2	97.01 (9)	C9—C8—P1	113.84 (18)
N1—Ni1—P2	166.27 (7)	N1—C9—C4	121.7 (2)
N2—Ni1—P2	85.97 (6)	N1—C9—C8	117.9 (2)
N1—Ni1—P1	86.13 (7)	C4—C9—C8	120.3 (2)
N2—Ni1—P1	165.68 (6)	P1—C10—H10A	109.5
P2—Ni1—P1	94.29 (3)	P1—C10—H10B	109.5
O3—Cl1—O2	110.15 (13)	H10A—C10—H10B	109.5
O3—Cl1—O1	109.95 (14)	P1—C10—H10C	109.5
O2—Cl1—O1	109.60 (13)	H10A—C10—H10C	109.5
O3—Cl1—O4	109.09 (14)	H10B—C10—H10C	109.5
O2—Cl1—O4	109.61 (13)	P1—C11—H11A	109.5
O1—Cl1—O4	108.41 (14)	P1—C11—H11B	109.5
O7—Cl2—O5	111.9 (4)	H11A—C11—H11B	109.5
O7—Cl2—O6	106.6 (3)	P1—C11—H11C	109.5
O5—Cl2—O6	111.0 (2)	H11A—C11—H11C	109.5
O7—Cl2—O8	105.4 (3)	H11B—C11—H11C	109.5
O5—Cl2—O8	110.3 (2)	N2—C12—C13	123.4 (2)
O6—Cl2—O8	111.5 (2)	N2—C12—H12	118.3
C8—P1—C11	105.12 (13)	C13—C12—H12	118.3
C8—P1—C10	105.93 (12)	C14—C13—C12	119.8 (3)
C11—P1—C10	106.05 (15)	C14—C13—H13	120.1
C8—P1—Ni1	99.90 (9)	C12—C13—H13	120.1
C11—P1—Ni1	117.20 (10)	C13—C14—C15	119.2 (2)
C10—P1—Ni1	120.75 (10)	C13—C14—H14	120.4
C22—P2—C21	105.52 (14)	C15—C14—H14	120.4
C22—P2—C19	106.08 (12)	C14—C15—C16	123.7 (2)
C21—P2—C19	104.32 (12)	C14—C15—C20	117.7 (2)
C22—P2—Ni1	118.50 (10)	C16—C15—C20	118.6 (2)
C21—P2—Ni1	120.92 (10)	C17—C16—C15	120.6 (2)
C19—P2—Ni1	99.35 (8)	C17—C16—H16	119.7
C1—N1—C9	117.8 (2)	C15—C16—H16	119.7
C1—N1—Ni1	123.61 (18)	C16—C17—C18	120.3 (2)
C9—N1—Ni1	118.53 (17)	C16—C17—H17	119.8
C12—N2—C20	117.4 (2)	C18—C17—H17	119.8
C12—N2—Ni1	124.45 (18)	C19—C18—C17	120.6 (3)
C20—N2—Ni1	118.18 (16)	C19—C18—H18	119.7
O9—N3—O10	123.2 (3)	C17—C18—H18	119.7
O9—N3—C23	118.2 (3)	C18—C19—C20	119.8 (2)
O10—N3—C23	118.6 (3)	C18—C19—P2	126.2 (2)
N1—C1—C2	123.0 (3)	C20—C19—P2	113.68 (18)
N1—C1—H1	118.5	N2—C20—C19	118.0 (2)
C2—C1—H1	118.5	N2—C20—C15	122.1 (2)
C3—C2—C1	119.5 (3)	C19—C20—C15	119.8 (2)
C3—C2—H2	120.3	P2—C21—H21A	109.5
C1—C2—H2	120.3	P2—C21—H21B	109.5
C2—C3—C4	119.3 (2)	H21A—C21—H21B	109.5
C2—C3—H3	120.3	P2—C21—H21C	109.5
C4—C3—H3	120.3	H21A—C21—H21C	109.5
C9—C4—C3	118.1 (3)	H21B—C21—H21C	109.5
C9—C4—C5	117.9 (3)	P2—C22—H22A	109.5
C3—C4—C5	123.9 (3)	P2—C22—H22B	109.5
C6—C5—C4	121.1 (3)	H22A—C22—H22B	109.5
C6—C5—H5	119.4	P2—C22—H22C	109.5
C4—C5—H5	119.4	H22A—C22—H22C	109.5
C5—C6—C7	120.4 (3)	H22B—C22—H22C	109.5
C5—C6—H6	119.8	N3—C23—H23A	109.5
C7—C6—H6	119.8	N3—C23—H23B	109.5
C8—C7—C6	119.7 (3)	H23A—C23—H23B	109.5
C8—C7—H7	120.1	N3—C23—H23C	109.5
C6—C7—H7	120.1	H23A—C23—H23C	109.5
C7—C8—C9	120.2 (2)	H23B—C23—H23C	109.5
C7—C8—P1	125.8 (2)

C9—N1—C1—C2	5.1 (4)	C20—N2—C12—C13	3.7 (4)
Ni1—N1—C1—C2	−173.7 (2)	Ni1—N2—C12—C13	−175.97 (19)
N1—C1—C2—C3	1.3 (4)	N2—C12—C13—C14	2.1 (4)
C1—C2—C3—C4	−4.8 (4)	C12—C13—C14—C15	−4.3 (4)
C2—C3—C4—C9	1.8 (4)	C13—C14—C15—C16	−177.8 (3)
C2—C3—C4—C5	−175.6 (3)	C13—C14—C15—C20	0.9 (4)
C9—C4—C5—C6	−3.4 (4)	C14—C15—C16—C17	175.8 (3)
C3—C4—C5—C6	173.9 (3)	C20—C15—C16—C17	−2.8 (4)
C4—C5—C6—C7	−0.5 (4)	C15—C16—C17—C18	−2.4 (4)
C5—C6—C7—C8	3.0 (4)	C16—C17—C18—C19	4.4 (4)
C6—C7—C8—C9	−1.5 (4)	C17—C18—C19—C20	−1.2 (4)
C6—C7—C8—P1	−177.4 (2)	C17—C18—C19—P2	−174.3 (2)
C11—P1—C8—C7	−47.4 (3)	C22—P2—C19—C18	−44.2 (3)
C10—P1—C8—C7	64.6 (3)	C21—P2—C19—C18	67.0 (3)
Ni1—P1—C8—C7	−169.2 (2)	Ni1—P2—C19—C18	−167.6 (2)
C11—P1—C8—C9	136.4 (2)	C22—P2—C19—C20	142.27 (19)
C10—P1—C8—C9	−111.6 (2)	C21—P2—C19—C20	−106.6 (2)
Ni1—P1—C8—C9	14.54 (19)	Ni1—P2—C19—C20	18.86 (19)
C1—N1—C9—C4	−8.2 (4)	C12—N2—C20—C19	170.6 (2)
Ni1—N1—C9—C4	170.70 (18)	Ni1—N2—C20—C19	−9.7 (3)
C1—N1—C9—C8	169.3 (2)	C12—N2—C20—C15	−7.3 (3)
Ni1—N1—C9—C8	−11.8 (3)	Ni1—N2—C20—C15	172.42 (18)
C3—C4—C9—N1	4.8 (4)	C18—C19—C20—N2	178.1 (2)
C5—C4—C9—N1	−177.7 (2)	P2—C19—C20—N2	−8.0 (3)
C3—C4—C9—C8	−172.6 (2)	C18—C19—C20—C15	−4.0 (4)
C5—C4—C9—C8	4.9 (4)	P2—C19—C20—C15	169.96 (18)
C7—C8—C9—N1	179.9 (2)	C14—C15—C20—N2	5.1 (4)
P1—C8—C9—N1	−3.6 (3)	C16—C15—C20—N2	−176.2 (2)
C7—C8—C9—C4	−2.6 (4)	C14—C15—C20—C19	−172.7 (2)
P1—C8—C9—C4	173.89 (19)	C16—C15—C20—C19	6.0 (4)

(SP-4-2)-cis-Bis[8-(dimethylphosphanyl)quinoline-κ²N,P]platinum(II) bis(tetrafluoroborate) acetonitrile monosolvate (2) top

Crystal data top

[Pt(C₁₁H₁₂NP)₂](BF₄)₂·C₂H₃N	F(000) = 1528
M_r = 788.13	D_x = 1.882 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
a = 7.9102 (3) Å	Cell parameters from 31045 reflections
b = 21.0833 (5) Å	θ = 3.1–27.5°
c = 16.7519 (4) Å	µ = 5.23 mm⁻¹
β = 95.3931 (11)°	T = 188 K
V = 2781.42 (15) Å³	Platelet, colorless
Z = 4	0.30 × 0.30 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	6350 independent reflections
Radiation source: fine-focus sealed tube	5435 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.042
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: numerical (NUMABS; Rigaku, 1999)	h = −10→10
T_min = 0.338, T_max = 0.594	k = −27→27
43967 measured reflections	l = −21→21

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0382P)² + 9.8949P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
6350 reflections	Δρ_max = 1.42 e Å⁻³
366 parameters	Δρ_min = −1.44 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pt1	0.64274 (2)	0.17364 (2)	0.20553 (2)	0.02183 (7)
P1	0.50347 (15)	0.24824 (5)	0.26806 (7)	0.0237 (2)
P2	0.80277 (15)	0.23745 (6)	0.13781 (7)	0.0247 (2)
F1	1.2369 (6)	−0.1256 (2)	0.0823 (5)	0.136 (3)
F2A	1.5089 (15)	−0.1511 (5)	0.0808 (7)	0.089 (2)	0.573 (10)
F3A	1.4191 (13)	−0.0455 (4)	0.0691 (7)	0.089 (2)	0.573 (10)
F4A	1.3835 (12)	−0.1067 (4)	0.1779 (6)	0.089 (2)	0.573 (10)
F2B	1.4392 (16)	−0.1049 (8)	0.0213 (10)	0.121 (4)	0.427 (10)
F3B	1.4100 (18)	−0.0423 (9)	0.1216 (12)	0.121 (4)	0.427 (10)
F4B	1.520 (2)	−0.1430 (9)	0.1262 (12)	0.121 (4)	0.427 (10)
F5	0.0397 (6)	0.3460 (3)	−0.0167 (5)	0.115 (2)
F6	0.2266 (7)	0.4071 (2)	−0.0644 (3)	0.0883 (15)
F7	0.1968 (10)	0.4023 (3)	0.0675 (3)	0.126 (3)
F8	0.3139 (5)	0.31996 (17)	0.0067 (2)	0.0566 (10)
N1	0.4883 (5)	0.11161 (18)	0.2672 (2)	0.0256 (8)
N2	0.7738 (5)	0.10240 (18)	0.1453 (2)	0.0270 (8)
N3	0.8437 (7)	−0.0443 (3)	0.3316 (4)	0.0521 (13)
C1	0.5191 (7)	0.0503 (2)	0.2795 (3)	0.0342 (11)
H1	0.6285	0.0343	0.2714	0.041*
C2	0.3965 (8)	0.0078 (3)	0.3041 (3)	0.0411 (13)
H2	0.4219	−0.0361	0.3103	0.049*
C3	0.2415 (7)	0.0304 (3)	0.3190 (3)	0.0395 (12)
H3	0.1547	0.0020	0.3317	0.047*
C4	0.2103 (6)	0.0963 (2)	0.3155 (3)	0.0310 (10)
C5	0.0599 (6)	0.1251 (3)	0.3391 (3)	0.0350 (11)
H5	−0.0327	0.0992	0.3512	0.042*
C6	0.0477 (7)	0.1893 (3)	0.3444 (3)	0.0346 (11)
H6	−0.0519	0.2077	0.3620	0.042*
C7	0.1812 (6)	0.2289 (2)	0.3239 (3)	0.0307 (10)
H7	0.1727	0.2736	0.3298	0.037*
C8	0.3228 (6)	0.2031 (2)	0.2955 (3)	0.0253 (9)
C9	0.3391 (6)	0.1368 (2)	0.2909 (3)	0.0254 (9)
C10	0.6062 (6)	0.2807 (2)	0.3599 (3)	0.0328 (11)
H10A	0.6548	0.2461	0.3938	0.039*
H10B	0.6968	0.3097	0.3474	0.039*
H10C	0.5227	0.3038	0.3884	0.039*
C11	0.4207 (7)	0.3163 (2)	0.2120 (3)	0.0353 (11)
H11A	0.3625	0.3023	0.1609	0.042*
H11B	0.3403	0.3389	0.2429	0.042*
H11C	0.5144	0.3447	0.2019	0.042*
C12	0.7232 (7)	0.0429 (2)	0.1333 (3)	0.0333 (11)
H12	0.6088	0.0325	0.1405	0.040*
C13	0.8316 (7)	−0.0059 (2)	0.1104 (3)	0.0380 (12)
H13	0.7911	−0.0482	0.1044	0.046*
C14	0.9946 (7)	0.0083 (3)	0.0970 (3)	0.0392 (12)
H14	1.0717	−0.0244	0.0861	0.047*
C15	1.0478 (6)	0.0725 (2)	0.0996 (3)	0.0311 (10)
C16	1.2074 (6)	0.0932 (3)	0.0757 (3)	0.0392 (12)
H16	1.2897	0.0628	0.0632	0.047*
C17	1.2421 (7)	0.1564 (3)	0.0707 (3)	0.0409 (13)
H17	1.3472	0.1696	0.0530	0.049*
C18	1.1258 (6)	0.2021 (3)	0.0913 (3)	0.0350 (11)
H18	1.1518	0.2459	0.0865	0.042*
C19	0.9729 (6)	0.1843 (2)	0.1186 (3)	0.0268 (10)
C20	0.9326 (6)	0.1191 (2)	0.1230 (3)	0.0256 (9)
C21	0.8949 (7)	0.3084 (2)	0.1834 (3)	0.0349 (11)
H21A	0.8043	0.3379	0.1944	0.042*
H21B	0.9617	0.2974	0.2338	0.042*
H21C	0.9688	0.3284	0.1469	0.042*
C22	0.7056 (7)	0.2620 (3)	0.0406 (3)	0.0354 (11)
H22A	0.6527	0.2252	0.0124	0.042*
H22B	0.6189	0.2942	0.0476	0.042*
H22C	0.7926	0.2798	0.0091	0.042*
C23	0.8162 (8)	−0.0480 (3)	0.3952 (4)	0.0437 (13)
C24	0.7834 (13)	−0.0553 (4)	0.4779 (4)	0.078 (2)
H24A	0.7717	−0.0134	0.5021	0.094*
H24B	0.8781	−0.0780	0.5071	0.094*
H24C	0.6783	−0.0794	0.4808	0.094*
B1	1.3953 (8)	−0.1035 (3)	0.0979 (4)	0.0361 (13)
B2	0.2039 (8)	0.3716 (3)	0.0001 (4)	0.0370 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.02079 (9)	0.02222 (10)	0.02284 (10)	0.00020 (6)	0.00396 (6)	0.00096 (7)
P1	0.0234 (6)	0.0233 (5)	0.0243 (6)	0.0018 (4)	0.0025 (4)	0.0014 (5)
P2	0.0221 (6)	0.0261 (6)	0.0258 (6)	−0.0021 (4)	0.0023 (4)	0.0032 (5)
F1	0.040 (2)	0.051 (3)	0.317 (10)	−0.003 (2)	0.017 (4)	0.009 (4)
F2A	0.104 (4)	0.057 (3)	0.106 (5)	0.009 (3)	0.014 (4)	0.015 (3)
F3A	0.104 (4)	0.057 (3)	0.106 (5)	0.009 (3)	0.014 (4)	0.015 (3)
F4A	0.104 (4)	0.057 (3)	0.106 (5)	0.009 (3)	0.014 (4)	0.015 (3)
F2B	0.071 (5)	0.136 (8)	0.158 (10)	−0.024 (5)	0.031 (6)	−0.015 (7)
F3B	0.071 (5)	0.136 (8)	0.158 (10)	−0.024 (5)	0.031 (6)	−0.015 (7)
F4B	0.071 (5)	0.136 (8)	0.158 (10)	−0.024 (5)	0.031 (6)	−0.015 (7)
F5	0.052 (3)	0.081 (3)	0.215 (7)	0.001 (2)	0.032 (4)	0.012 (4)
F6	0.108 (4)	0.087 (3)	0.075 (3)	0.032 (3)	0.037 (3)	0.040 (3)
F7	0.207 (7)	0.110 (4)	0.057 (3)	0.077 (5)	−0.008 (4)	−0.027 (3)
F8	0.053 (2)	0.054 (2)	0.062 (2)	0.0172 (17)	0.0060 (18)	0.0040 (18)
N1	0.0241 (19)	0.0264 (19)	0.0269 (19)	0.0009 (15)	0.0066 (15)	0.0044 (16)
N2	0.028 (2)	0.027 (2)	0.0252 (19)	−0.0004 (16)	0.0028 (16)	−0.0020 (16)
N3	0.052 (3)	0.049 (3)	0.057 (3)	0.003 (2)	0.013 (3)	0.004 (3)
C1	0.040 (3)	0.028 (2)	0.037 (3)	0.004 (2)	0.012 (2)	0.004 (2)
C2	0.058 (4)	0.026 (3)	0.042 (3)	0.000 (2)	0.018 (3)	0.006 (2)
C3	0.045 (3)	0.034 (3)	0.042 (3)	−0.010 (2)	0.014 (2)	0.003 (2)
C4	0.030 (2)	0.037 (3)	0.026 (2)	−0.005 (2)	0.0045 (19)	0.000 (2)
C5	0.025 (2)	0.049 (3)	0.032 (3)	−0.003 (2)	0.007 (2)	0.004 (2)
C6	0.030 (3)	0.047 (3)	0.028 (2)	0.009 (2)	0.006 (2)	0.005 (2)
C7	0.030 (2)	0.038 (3)	0.025 (2)	0.006 (2)	0.0046 (19)	0.001 (2)
C8	0.026 (2)	0.031 (2)	0.019 (2)	0.0008 (18)	0.0018 (17)	0.0029 (18)
C9	0.026 (2)	0.029 (2)	0.022 (2)	0.0007 (18)	0.0033 (18)	0.0014 (18)
C10	0.032 (3)	0.036 (3)	0.030 (2)	0.000 (2)	0.001 (2)	−0.007 (2)
C11	0.033 (3)	0.031 (3)	0.043 (3)	0.004 (2)	0.006 (2)	0.009 (2)
C12	0.035 (3)	0.030 (2)	0.036 (3)	−0.004 (2)	0.010 (2)	−0.004 (2)
C13	0.052 (3)	0.025 (2)	0.038 (3)	0.000 (2)	0.013 (2)	−0.004 (2)
C14	0.047 (3)	0.038 (3)	0.033 (3)	0.013 (2)	0.007 (2)	−0.002 (2)
C15	0.029 (2)	0.039 (3)	0.025 (2)	0.006 (2)	0.0046 (19)	−0.003 (2)
C16	0.026 (3)	0.057 (3)	0.034 (3)	0.009 (2)	0.004 (2)	−0.004 (3)
C17	0.026 (3)	0.062 (4)	0.035 (3)	−0.007 (2)	0.007 (2)	−0.010 (3)
C18	0.028 (2)	0.045 (3)	0.033 (3)	−0.007 (2)	0.008 (2)	−0.003 (2)
C19	0.024 (2)	0.033 (2)	0.024 (2)	−0.0016 (18)	0.0028 (18)	−0.0035 (19)
C20	0.022 (2)	0.031 (2)	0.023 (2)	0.0034 (18)	0.0017 (17)	0.0004 (19)
C21	0.030 (3)	0.029 (2)	0.046 (3)	−0.004 (2)	0.001 (2)	−0.002 (2)
C22	0.034 (3)	0.043 (3)	0.029 (2)	−0.001 (2)	0.000 (2)	0.007 (2)
C23	0.044 (3)	0.030 (3)	0.057 (4)	−0.006 (2)	0.005 (3)	−0.001 (3)
C24	0.125 (7)	0.057 (4)	0.054 (4)	−0.025 (5)	0.020 (5)	0.005 (4)
B1	0.038 (3)	0.028 (3)	0.044 (4)	0.003 (2)	0.010 (3)	−0.002 (3)
B2	0.043 (3)	0.034 (3)	0.036 (3)	0.005 (3)	0.014 (3)	0.001 (3)

Geometric parameters (Å, º) top

Pt1—N1	2.123 (4)	C6—C7	1.414 (7)
Pt1—N2	2.132 (4)	C6—H6	0.9500
Pt1—P2	2.2293 (12)	C7—C8	1.371 (6)
Pt1—P1	2.2365 (12)	C7—H7	0.9500
P1—C11	1.804 (5)	C8—C9	1.405 (7)
P1—C10	1.805 (5)	C10—H10A	0.9800
P1—C8	1.812 (5)	C10—H10B	0.9800
P2—C21	1.802 (5)	C10—H10C	0.9800
P2—C19	1.804 (5)	C11—H11A	0.9800
P2—C22	1.810 (5)	C11—H11B	0.9800
F1—B1	1.340 (8)	C11—H11C	0.9800
F2A—B1	1.395 (13)	C12—C13	1.416 (7)
F3A—B1	1.334 (11)	C12—H12	0.9500
F4A—B1	1.353 (11)	C13—C14	1.363 (8)
F2B—B1	1.361 (17)	C13—H13	0.9500
F3B—B1	1.351 (18)	C14—C15	1.416 (8)
F4B—B1	1.35 (2)	C14—H14	0.9500
F5—B2	1.410 (8)	C15—C20	1.421 (6)
F6—B2	1.341 (7)	C15—C16	1.428 (7)
F7—B2	1.309 (8)	C16—C17	1.366 (8)
F8—B2	1.391 (7)	C16—H16	0.9500
N1—C1	1.329 (6)	C17—C18	1.398 (8)
N1—C9	1.386 (6)	C17—H17	0.9500
N2—C12	1.326 (6)	C18—C19	1.384 (7)
N2—C20	1.389 (6)	C18—H18	0.9500
N3—C23	1.110 (8)	C19—C20	1.414 (6)
C1—C2	1.409 (7)	C21—H21A	0.9800
C1—H1	0.9500	C21—H21B	0.9800
C2—C3	1.360 (8)	C21—H21C	0.9800
C2—H2	0.9500	C22—H22A	0.9800
C3—C4	1.410 (7)	C22—H22B	0.9800
C3—H3	0.9500	C22—H22C	0.9800
C4—C9	1.421 (7)	C23—C24	1.441 (9)
C4—C5	1.424 (7)	C24—H24A	0.9800
C5—C6	1.361 (8)	C24—H24B	0.9800
C5—H5	0.9500	C24—H24C	0.9800

N1—Pt1—N2	97.13 (15)	N2—C12—H12	118.4
N1—Pt1—P2	178.51 (11)	C13—C12—H12	118.4
N2—Pt1—P2	81.93 (11)	C14—C13—C12	119.4 (5)
N1—Pt1—P1	82.76 (11)	C14—C13—H13	120.3
N2—Pt1—P1	179.55 (11)	C12—C13—H13	120.3
P2—Pt1—P1	98.17 (4)	C13—C14—C15	119.2 (5)
C11—P1—C10	104.7 (3)	C13—C14—H14	120.4
C11—P1—C8	107.1 (2)	C15—C14—H14	120.4
C10—P1—C8	106.6 (2)	C14—C15—C20	118.3 (5)
C11—P1—Pt1	119.12 (19)	C14—C15—C16	123.4 (5)
C10—P1—Pt1	117.60 (17)	C20—C15—C16	118.2 (5)
C8—P1—Pt1	100.60 (16)	C17—C16—C15	120.2 (5)
C21—P2—C19	108.2 (2)	C17—C16—H16	119.9
C21—P2—C22	105.4 (3)	C15—C16—H16	119.9
C19—P2—C22	106.1 (2)	C16—C17—C18	121.2 (5)
C21—P2—Pt1	120.76 (19)	C16—C17—H17	119.4
C19—P2—Pt1	100.65 (16)	C18—C17—H17	119.4
C22—P2—Pt1	114.64 (18)	C19—C18—C17	120.6 (5)
C1—N1—C9	118.5 (4)	C19—C18—H18	119.7
C1—N1—Pt1	124.7 (3)	C17—C18—H18	119.7
C9—N1—Pt1	116.6 (3)	C18—C19—C20	119.3 (4)
C12—N2—C20	117.8 (4)	C18—C19—P2	125.4 (4)
C12—N2—Pt1	125.8 (3)	C20—C19—P2	114.7 (3)
C20—N2—Pt1	116.2 (3)	N2—C20—C19	118.3 (4)
N1—C1—C2	122.9 (5)	N2—C20—C15	121.2 (4)
N1—C1—H1	118.6	C19—C20—C15	120.3 (4)
C2—C1—H1	118.6	P2—C21—H21A	109.5
C3—C2—C1	119.2 (5)	P2—C21—H21B	109.5
C3—C2—H2	120.4	H21A—C21—H21B	109.5
C1—C2—H2	120.4	P2—C21—H21C	109.5
C2—C3—C4	119.7 (5)	H21A—C21—H21C	109.5
C2—C3—H3	120.2	H21B—C21—H21C	109.5
C4—C3—H3	120.2	P2—C22—H22A	109.5
C3—C4—C9	118.5 (5)	P2—C22—H22B	109.5
C3—C4—C5	123.8 (5)	H22A—C22—H22B	109.5
C9—C4—C5	117.6 (5)	P2—C22—H22C	109.5
C6—C5—C4	120.6 (5)	H22A—C22—H22C	109.5
C6—C5—H5	119.7	H22B—C22—H22C	109.5
C4—C5—H5	119.7	N3—C23—C24	177.7 (7)
C5—C6—C7	120.8 (5)	C23—C24—H24A	109.5
C5—C6—H6	119.6	C23—C24—H24B	109.5
C7—C6—H6	119.6	H24A—C24—H24B	109.5
C8—C7—C6	120.2 (5)	C23—C24—H24C	109.5
C8—C7—H7	119.9	H24A—C24—H24C	109.5
C6—C7—H7	119.9	H24B—C24—H24C	109.5
C7—C8—C9	119.8 (4)	F3A—B1—F1	114.2 (7)
C7—C8—P1	124.7 (4)	F1—B1—F4B	119.8 (9)
C9—C8—P1	115.5 (3)	F1—B1—F3B	116.3 (8)
N1—C9—C8	118.8 (4)	F4B—B1—F3B	116.6 (12)
N1—C9—C4	120.3 (4)	F3A—B1—F4A	115.4 (8)
C8—C9—C4	120.7 (4)	F1—B1—F4A	91.4 (7)
P1—C10—H10A	109.5	F1—B1—F2B	97.2 (8)
P1—C10—H10B	109.5	F4B—B1—F2B	94.3 (11)
H10A—C10—H10B	109.5	F3B—B1—F2B	106.0 (11)
P1—C10—H10C	109.5	F3A—B1—F2A	118.0 (8)
H10A—C10—H10C	109.5	F1—B1—F2A	108.5 (7)
H10B—C10—H10C	109.5	F4A—B1—F2A	105.8 (7)
P1—C11—H11A	109.5	F7—B2—F6	116.0 (6)
P1—C11—H11B	109.5	F7—B2—F8	113.3 (6)
H11A—C11—H11B	109.5	F6—B2—F8	111.8 (5)
P1—C11—H11C	109.5	F7—B2—F5	104.4 (6)
H11A—C11—H11C	109.5	F6—B2—F5	104.1 (6)
H11B—C11—H11C	109.5	F8—B2—F5	105.9 (5)
N2—C12—C13	123.2 (5)

C9—N1—C1—C2	10.0 (7)	C20—N2—C12—C13	9.6 (7)
Pt1—N1—C1—C2	−165.3 (4)	Pt1—N2—C12—C13	−164.6 (4)
N1—C1—C2—C3	−2.5 (8)	N2—C12—C13—C14	−2.3 (8)
C1—C2—C3—C4	−4.8 (8)	C12—C13—C14—C15	−5.4 (8)
C2—C3—C4—C9	4.3 (8)	C13—C14—C15—C20	5.4 (7)
C2—C3—C4—C5	−172.4 (5)	C13—C14—C15—C16	−171.1 (5)
C3—C4—C5—C6	171.1 (5)	C14—C15—C16—C17	172.3 (5)
C9—C4—C5—C6	−5.6 (7)	C20—C15—C16—C17	−4.2 (7)
C4—C5—C6—C7	2.3 (8)	C15—C16—C17—C18	2.2 (8)
C5—C6—C7—C8	2.4 (7)	C16—C17—C18—C19	1.1 (8)
C6—C7—C8—C9	−3.5 (7)	C17—C18—C19—C20	−2.1 (7)
C6—C7—C8—P1	−179.3 (4)	C17—C18—C19—P2	−173.6 (4)
C11—P1—C8—C7	−43.4 (5)	C21—P2—C19—C18	−39.4 (5)
C10—P1—C8—C7	68.3 (4)	C22—P2—C19—C18	73.3 (5)
Pt1—P1—C8—C7	−168.5 (4)	Pt1—P2—C19—C18	−167.0 (4)
C11—P1—C8—C9	140.6 (4)	C21—P2—C19—C20	148.8 (4)
C10—P1—C8—C9	−107.7 (4)	C22—P2—C19—C20	−98.5 (4)
Pt1—P1—C8—C9	15.5 (3)	Pt1—P2—C19—C20	21.2 (4)
C1—N1—C9—C8	165.5 (4)	C12—N2—C20—C19	166.2 (4)
Pt1—N1—C9—C8	−18.9 (5)	Pt1—N2—C20—C19	−19.0 (5)
C1—N1—C9—C4	−10.1 (7)	C12—N2—C20—C15	−9.3 (7)
Pt1—N1—C9—C4	165.5 (3)	Pt1—N2—C20—C15	165.4 (3)
C7—C8—C9—N1	−175.6 (4)	C18—C19—C20—N2	−175.7 (4)
P1—C8—C9—N1	0.6 (5)	P2—C19—C20—N2	−3.3 (6)
C7—C8—C9—C4	−0.1 (7)	C18—C19—C20—C15	−0.1 (7)
P1—C8—C9—C4	176.2 (3)	P2—C19—C20—C15	172.3 (4)
C3—C4—C9—N1	3.1 (7)	C14—C15—C20—N2	2.0 (7)
C5—C4—C9—N1	−179.9 (4)	C16—C15—C20—N2	178.6 (4)
C3—C4—C9—C8	−172.4 (5)	C14—C15—C20—C19	−173.5 (4)
C5—C4—C9—C8	4.6 (7)	C16—C15—C20—C19	3.2 (7)

Funding information

This work was partly supported by JSPS KAKENHI Grant No. 18 K05146.

References

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Volume 76| Part 12| December 2020| Pages 1813-1817

https://doi.org/10.1107/S2056989020014437

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Comparison of mol­ecular structures of cis-bis­­[8-(di­methyl­phosphan­yl)quinoline]­nickel(II) and -platinum(II) complex cations

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Funding information

References

research communications

Comparison of molecular structures of cis-bis[8-(dimethylphosphanyl)quinoline]nickel(II) and -platinum(II) complex cations

3. Supramolecular features