Crystal and mol­ecular structures of di­chlorido­palladium(II) containing 2-methyl- or 2-phenyl-8-(diphenyphosphan­yl)quinoline

Mori, M.; Namioka, A.; Suzuki, T.

doi:10.1107/S2056989020016096

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ISSN: 2056-9890

Volume 77| Part 1| January 2021| Pages 52-57

https://doi.org/10.1107/S2056989020016096

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Crystal and molecular structures of dichloridopalladium(II) containing 2-methyl- or 2-phenyl-8-(diphenyphosphanyl)quinoline

Masatoshi Mori,^a Atsushi Namioka ^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 M. Weil, Vienna University of Technology, Austria (Received 23 November 2020; accepted 10 December 2020; online 1 January 2021)

The crystal structures of dichloridopalladium(II) complexes bearing 2-methyl- and 2-phenyl-8-(diphenylphosphanyl)quinoline, namely, dichlorido[8-(diphenylphosphanyl)-2-methylquinoline-κ²N,P]palladium(II), [PdCl₂(C₂₂H₁₈NP)] (1) and dichlorido[8-(diphenylphosphanyl)-2-phenylquinoline-κ²N,P]palladium(II), [PdCl₂(C₂₇H₂₀NP)] (2), were analyzed and compared to that of the 8-(diphenylphosphanyl)quinoline (PQ^H) analogue (3). In all three complexes, the phosphanylquinoline moiety acts as a bidentate P,N-donating chelate ligand. In the PQ^H complex (3), the Pd^II center has a typical planar coordination environment; however, both the methyl- and phenyl-substituted phosphanylquinoline (PQ^Me and PQ^Ph, respectively) complexes (1) and (2) exhibit a considerable tetrahedral distortion around the Pd^II center, as parameterized by the τ₄ values of 0.1555 (4) and 0.1438 (4) for (1) and (2), respectively. The steric interaction from the substituted group introduced at the 2-position of the quinoline ring enforces the cis-positioned Cl ligand to be displaced from the ideal coordination plane. Also, the ideally planar phosphanylquinoline five-membered chelate ring shows a large bending deformation by the displacement of the Pd^II center from the quinoline plane. In addition, in the phenyl-substituted complex (3), the coordinating quinolyl and the substituted phenyl rings are not co-planar to each other, having a dihedral angle of 33.08 (7)°. This twist conformation prohibits any intermolecular π–π stacking interaction between the quinoline planes, which is observed in the crystals of complexes (1) and (2).

Keywords: 8-quinolylphosphane; square-planar coordination; tetrahedral distortion; intermolecular stacking interaction.; crystal structure.

CCDC references: 2049480; 2049479

1. Chemical context

8-Quinolylphosphanes are competent ligands for various functional coordination compounds, because they consist of a strongly σ-donating phosphane donor group and a π-conjugated quinoline moiety and form a stable planar five-membered chelate ring on coordination to a metal center (Cai et al., 2018 ; Hopkins et al., 2019 ; Scattolin et al., 2017 ). In one of our previous studies, it was revealed that 8-(diphenylphosphanyl)quinoline (PQ^H) in the simplest dichloridopalladium(II) complex, [PdCl₂(PQ^H)] (3), exhibits a strong trans influence of the diphenylphosphanyl donor group and an intermolecular π–π stacking interaction between the quinoline ring systems (Suzuki et al., 2015 ). Also, in the bis(PQ^H)-type Ni^II, Pd^II and Pt^II (M^II) complexes, [M^II(PQ^H)₂]X₂ (X = ClO₄, BF₄ or CF₃SO₃), the cis(P,P)-isomers are preferably formed due to the above-mentioned trans influence, but the mutually cis-positioned quinoline groups give a steric congestion between them, causing the coordination environment around M^II to be distorted (Suzuki, 2004 ; Mori et al., 2020 ). When a methyl or phenyl group substituted at the ortho-position of the quinoline-N atom of PQ^H is used for complexation, for example in 2-methyl-8-(diphenylphosphanyl)quinoline (PQ^Me) (1) or 2-phenyl-8-(diphenylphosphanyl)quinoline (PQ^Ph) (2), a much larger steric hindrance would be expected at the cis-position of the coordinating quinoline-N donor site. In the present study we reveal the characteristic structural features of the simplest PdCl₂ complexes bearing PQ^Me (1) and PQ^Ph (2) chelate ligands.

2. Structural commentary

In the crystals of (1) and (2), the quinolylphosphane moiety coordinates to a Pd^II center in a bidentate κ²P,N mode, and the coordination environment around the Pd^II center is roughly square-planar with two additional chlorido ligands. The analogous PQ^H complex (3) has a typical planar environment (Suzuki et al., 2015); the τ₄ value (Yang et al., 2007 ) indicating the tetrahedral distortion around the four-coordinate Pd^II center is here only 0.0552 (4). The coordination plane (defined by the central Pd and four donor atoms) and the quinoline plane are almost co-planar, with their dihedral angle being 8.58 (3)°. The Pd1—P1 and Pd1—N1 bond lengths in the structure of (3) are 2.2026 (6) and 2.065 (2) Å, respectively, and the P1—Pd1—N1 chelate bite angle is 84.75 (6)°. The Pd—Cl1 (trans to P1) and Pd1—Cl2 (trans to N1) bond lengths are 2.3716 (7) and 2.2885 (8) Å, respectively, indicating a strong trans influence of the Ph₂P– donor group.

In the PQ^Me complex (1) (Fig. 1), the coordination environment around the Pd^II center is apparently distorted; the τ₄ value is 0.1555 (4). The steric requirement from the 2-methyl substituent of the coordinating quinoline group causes the Cl ligand in the cis-position to be pushed away (Fig. 2). Thus, the Cl1 atom is considerably displaced from the Pd^II coordination plane (defined by Pd1, Cl2, P1 and N1) by 0.554 (1) Å, and the P1—Pd1—Cl1 bond angle is 166.74 (2)°, as compared to the N1—Pd1—Cl2 angle of 171.32 (5)°. More importantly, the PQ^Me chelate ring is no longer planar. The Pd1 atom is displaced by 0.755 (2) Å from the chelating ligand plane (defined by P1, C8, C9 and N1), and the dihedral angle φ_C between the plane [Pd1,P1,N1] and the quinoline plane (defined by N1 and C1–C9) is 25.35 (3)°. Thus, an envelope-type deformation of the chelate ring is observed. This distortion would weaken the Pd—N bond, because the direction of the lone-pair electrons on the N atom does not match with the Pd^II acceptor d-orbital. In fact, the Pd1—N1 bond length of 2.0971 (17) Å in (1) is slightly longer than that in (3). Other coordination bonds and angles are collated in Table 1 and are comparable to those in (3).

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

Pd1—N1	2.0971 (17)	Pd1—Cl2	2.2823 (6)
Pd1—P1	2.1910 (5)	Pd1—Cl1	2.3742 (6)

N1—Pd1—P1	83.52 (5)	N1—Pd1—Cl1	98.30 (5)
N1—Pd1—Cl2	171.32 (5)	P1—Pd1—Cl1	166.74 (2)
P1—Pd1—Cl2	88.25 (2)	Cl2—Pd1—Cl1	90.34 (2)

Figure 1
The molecular structure of [PdCl₂(PQ^Me)] (1), showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level.

Figure 2
Perspective (a) top and (b) side views of a dimeric unit of (1), showing the distortion of the coordination environment around Pd^II and the intermolecular π–π stacking interaction between the quinoline ring systems. Color code: Pd, blueish purple; P, orange; N, blue; C, black and H, gray.

The PQ^Ph complex (2) shows a more explicit distortion of the coordination environment on the quinolylphosphane ligand due to the 2-phenyl substitution group (Figs. 3 and 4). The τ₄ value is 0.1438 (4), and the Cl1 atom is displaced from the Pd^II coordination plane (defined by Pd1, Cl2, P1 and N1) by 0.571 (1) Å. The P1—Pd1—Cl1 and N1—Pd1—Cl2 bond angles are 165.930 (19) and 173.78 (5)°, respectively. The Pd1 atom is displaced by 0.864 (2) Å from the chelating ligand plane (defined by P1, C8, C9 and N1), and the dihedral angle φ_C between the plane [Pd1,P1,N1] and the quinoline plane (defined by N1 and C1–C9) is 32.56 (3)°. In addition, the substituted phenyl plane is twisted from the attached quinoline plane with a dihedral angle of 33.08 (7)°. Table 2 lists selected bond lengths and angles.

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

Pd1—N1	2.0806 (15)	Pd1—Cl2	2.2769 (5)
Pd1—P1	2.2036 (6)	Pd1—Cl1	2.3738 (6)

N1—Pd1—P1	83.24 (5)	N1—Pd1—Cl1	94.56 (5)
N1—Pd1—Cl2	173.78 (5)	P1—Pd1—Cl1	165.930 (19)
P1—Pd1—Cl2	90.56 (2)	Cl2—Pd1—Cl1	91.57 (2)

Figure 3
The molecular structure of [PdCl₂(PQ^Ph)] (2), showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level.

Figure 4
A perspective side view of (2), showing the distortion of the coordination environment around Pd^II. Color code: Pd, blueish purple; P, orange; N, blue; C, black and H, gray.

3. Supramolecular features

In the crystal structure, the molecular PQ^H complex (3) forms a dimer by an intermolecular π–π stacking interaction between the quinoline ring systems. A similar stacking interaction is observed in the crystal structure of the PQ^Me complex (1) (Fig. 2). The shortest intermolecular contact distance is 3.322 (3) Å for C2⋯C6ⁱ [symmetry code: (i) −x + 1, −y + 1, −z). By contrast, the PQ^Ph complex (2) does not show a similar stacking interaction to the above examples, because the twist motion of the attached phenyl group prohibits a full π–π stacking interaction between the molecules (Fig. 4). The shortest intermolecular contact distance in (2) is 3.549 (3) Å for C2⋯C3ⁱⁱ [symmetry code (ii) −x + 1, −y + 2, −z + 1]. There are no other obvious supramolecular features in the crystal structures of (1) and (2) (Figs. 5 and 6).

Figure 5
The packing of [PdCl₂(PQ^Me)] (1), viewed along the b axis. Color code: Pd, blueish purple; P, orange; N, blue; C, black and H, gray.

Figure 6
The packing of [PdCl₂(PQ^Ph)] (2), viewed along the b axis. Color code: Pd, blueish purple; P, orange; N, blue; C, black and H, gray.

4. Database survey

Crystal structures of the following transition-metal complexes containing PQ^Me or PQ^Ph were retrieved from the Cambridge Structural Database (CSD, version 5.41, last update May 2020; Groom et al., 2016 ): [Cu(PQ^Me)₂]PF₆ (refcode NOPNOW; Tsukuda et al., 2009 ), [Cu(PQ^Me){(Ph₂PC₆H₄)₂O}]BF₄·CH₂Cl₂ (OGUYEV; Qin et al., 2009 ), [{Ni(PQ^Me)Cl}₂(μ-Cl)₂]·CH₂Cl₂ (MUMDAZ; Sun et al., 2002 ), two organometallic Pd^II complexes (BUPMIK and BUPMOQ; Canovese et al., 2015 ). We have recently reported some Ni^II, Pd^II and Pt^II (M^II) complexes bearing PQ^R: [M(PQ^R)₂]X₂ (X = Br, BF₄ or CF₃SO₃) (Mori et al., 2020) and [Pt(ppy)(PQ^R)]BF₄ [ppy = 2-(2′-pyridyl)phenyl; Mori & Suzuki, 2020 ]. A related palladium(II) complex containing 2-methyl-8-(methylphenylphosphanyl)quinoline has also been reported (PUMDAD; Bock et al., 2010 ).

5. Synthesis and crystallization

The ligands, PQ^Me and PQ^Ph, were prepared according to the methods reported previously (Mori & Suzuki, 2020). Complex (1) was prepared as follows: under a nitrogen atmosphere, a dichloromethane solution (10 ml) of PQ^Me (0.109 g, 0.334 mmol) was added under stirring to a dichloromethane solution (8 ml) of [PdCl₂(PhCN)₂] (PhCN = benzonitrile) (0.121 g, 0.315 mmol), and the mixture was stirred overnight at room temperature. The resulting solution was concentrated using a rotary evaporator, and diethyl ether was added under stirring to the concentrate, giving a yellow precipitate, which was collected by filtration, washed with diethyl ether (10 ml), and dried in vacuo. Yield: 0.142 g (92%). Analysis found: C, 51.03; H, 3.67; N, 2.99%. Calculated for C₂₂H₁₈Cl₂NPPd·0.7H₂O: C, 51.08; H, 3.78; N, 2.71%. Yellow needle-like crystals of (1) were obtained by recrystallization from an acetonitrile solution by diffusion of diisopropyl ether.

Complex (2) was prepared as follows: under a nitrogen atmosphere, a dichloromethane solution (10 ml) of PQ^Ph (0.071 g, 0.18 mmol) was added under stirring to a dichloromethane solution (10 ml) of [PdCl₂(PhCN)₂] (0.070 g, 0.18 mmol), and the mixture was stirred overnight at room temperature. The resulting brown precipitate was filtered off, and the filtrate was concentrated under reduced pressure. Diethyl ether was added under stirring to the concentrate, giving a yellow precipitate, which was collected by filtration, washed with diethyl ether (10 ml), and dried in vacuo. Yield: 0.041 g (40%). Analysis found: C, 56.23; H, 3.50; N, 2.56%. Calculated for C₂₇H₂₀Cl₂NPPd: C, 57.22; H, 3.56; N, 2.47%. Yellow block-like crystals of (2) were obtained by recrystallization from an acetonitrile solution by diffusion of diisopropyl ether.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 (aromatic) or 0.98 (methyl) Å and U_iso = 1.2U_eq(C). For the refinement of (2), two reflections (4 $[\overline{1}]$ 1, $[\overline{7}]$ 98) were omitted because they showed a significantly lower intensity than calculated, most probably caused by obstruction from the beam stop.

Table 3
Experimental details

	Complex (1)	Complex (2)
Crystal data
Chemical formula	[PdCl₂(C₂₂H₁₈NP)]	[PdCl₂(C₂₇H₂₀NP)]
M_r	504.64	566.71
Crystal system, space group	Monoclinic, C2/c	Triclinic, P $[\overline{1}]$
Temperature (K)	188	188
a, b, c (Å)	13.8153 (5), 15.5676 (8), 18.9683 (5)	9.6582 (13), 9.8765 (14), 13.0748 (14)
α, β, γ (°)	90, 108.733 (2), 90	102.011 (4), 90.426 (4), 109.827 (4)
V (Å³)	3863.4 (3)	1143.4 (3)
Z	8	2
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	1.33	1.13
Crystal size (mm)	0.50 × 0.20 × 0.15	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID	Rigaku R-AXIS RAPID
Absorption correction	Numerical (NUMABS; Rigaku, 1999 )	Numerical (NUMABS; Rigaku, 1999)
T_min, T_max	0.662, 0.819	0.640, 0.797
No. of measured, independent and observed [I > 2σ(I)] reflections	18561, 4438, 3976	11339, 5194, 4682
R_int	0.039	0.027
(sin θ/λ)_max (Å⁻¹)	0.649	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.063, 1.05	0.025, 0.064, 1.06
No. of reflections	4438	5192
No. of parameters	245	289
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.34	0.74, −0.59
Computer programs: PROCESS-AUTO (Rigaku, 1998 ), CrystalStructure (Rigaku, 2010 ), DIRDIF99 (Beurskens et al., 1999 ), Il Milione (Burla et al., 2012 ), SHELXL2014/7 (Sheldrick, 2015 ), CrystalMaker (CrystalMaker, 2017 ), and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 2049480; 2049479

Crystal structure: contains datablocks complex1, complex2. DOI: https://doi.org/10.1107/S2056989020016096/wm5591sup1.cif

Structure factors: contains datablock complex1. DOI: https://doi.org/10.1107/S2056989020016096/wm5591complex1sup4.hkl

Structure factors: contains datablock complex2. DOI: https://doi.org/10.1107/S2056989020016096/wm5591complex2sup5.hkl

checkCIF report

Computing details top

For both structures, data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku, 2010). Program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999) for complex1; Il Milione (Burla et al., 2012) for complex2. For both structures, program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: CrystalMaker (CrystalMaker, 2017); software used to prepare material for publication: publCIF (Westrip, 2010).

Dichlorido[8-(diphenylphosphanyl)-2-methylquinoline-κ²N,P]palladium(II) (complex1) top

Crystal data top

[PdCl₂(C₂₂H₁₈NP)]	F(000) = 2016
M_r = 504.64	D_x = 1.735 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
a = 13.8153 (5) Å	Cell parameters from 15062 reflections
b = 15.5676 (8) Å	θ = 3.1–27.6°
c = 18.9683 (5) Å	µ = 1.33 mm⁻¹
β = 108.733 (2)°	T = 188 K
V = 3863.4 (3) Å³	Needle, yellow
Z = 8	0.50 × 0.20 × 0.15 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4438 independent reflections
Radiation source: fine-focus sealed tube	3976 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: numerical (NUMABS; Rigaku, 1999)	h = −17→17
T_min = 0.662, T_max = 0.819	k = −20→20
18561 measured reflections	l = −23→25

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0257P)² + 5.1054P] where P = (F_o² + 2F_c²)/3
4438 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.34 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
Pd1	0.18958 (2)	0.00853 (2)	0.12906 (2)	0.02335 (6)
Cl1	0.18633 (5)	−0.13050 (4)	0.07691 (4)	0.04342 (15)
Cl2	0.14113 (5)	−0.04783 (4)	0.22366 (3)	0.03709 (14)
P1	0.22803 (4)	0.12790 (3)	0.19320 (3)	0.02356 (11)
N1	0.23191 (12)	0.07847 (11)	0.04910 (9)	0.0238 (3)
C1	0.20531 (16)	0.06113 (14)	−0.02343 (12)	0.0274 (4)
C2	0.26023 (17)	0.09721 (15)	−0.06751 (12)	0.0314 (5)
H2	0.2439	0.0806	−0.1182	0.038*
C3	0.33556 (16)	0.15490 (15)	−0.03855 (12)	0.0308 (5)
H3	0.3744	0.1764	−0.0679	0.037*
C4	0.35637 (15)	0.18305 (14)	0.03552 (12)	0.0269 (4)
C5	0.42756 (16)	0.24877 (15)	0.06901 (13)	0.0314 (5)
H5	0.4667	0.2742	0.0415	0.038*
C6	0.44088 (16)	0.27612 (15)	0.13956 (13)	0.0334 (5)
H6	0.4893	0.3199	0.1610	0.040*
C7	0.38300 (16)	0.23959 (14)	0.18060 (12)	0.0303 (5)
H7	0.3902	0.2604	0.2291	0.036*
C8	0.31559 (15)	0.17359 (13)	0.15078 (11)	0.0249 (4)
C9	0.30212 (14)	0.14371 (13)	0.07806 (11)	0.0232 (4)
C10	0.11417 (19)	0.00666 (15)	−0.06008 (13)	0.0354 (5)
H10A	0.0587	0.0218	−0.0406	0.042*
H10B	0.1321	−0.0540	−0.0497	0.042*
H10C	0.0919	0.0164	−0.1140	0.042*
C11	0.12787 (16)	0.20610 (14)	0.17993 (12)	0.0268 (4)
C12	0.03231 (17)	0.18947 (16)	0.12721 (13)	0.0340 (5)
H12	0.0190	0.1349	0.1037	0.041*
C13	−0.04303 (18)	0.25209 (18)	0.10918 (15)	0.0405 (6)
H13	−0.1078	0.2408	0.0733	0.049*
C14	−0.0230 (2)	0.33035 (18)	0.14365 (15)	0.0447 (6)
H14	−0.0744	0.3735	0.1318	0.054*
C15	0.0717 (2)	0.34742 (17)	0.19588 (15)	0.0425 (6)
H15	0.0843	0.4023	0.2190	0.051*
C16	0.14790 (18)	0.28583 (15)	0.21475 (13)	0.0338 (5)
H16	0.2124	0.2977	0.2506	0.041*
C17	0.29830 (16)	0.11805 (14)	0.29131 (11)	0.0270 (4)
C18	0.25801 (18)	0.14295 (16)	0.34621 (13)	0.0349 (5)
H18	0.1928	0.1697	0.3333	0.042*
C19	0.3144 (2)	0.12828 (17)	0.42099 (13)	0.0404 (6)
H19	0.2880	0.1471	0.4589	0.048*
C20	0.4061 (2)	0.08758 (16)	0.44024 (13)	0.0402 (6)
H20	0.4427	0.0771	0.4912	0.048*
C21	0.44627 (18)	0.06140 (16)	0.38595 (13)	0.0384 (5)
H21	0.5102	0.0325	0.3994	0.046*
C22	0.39295 (17)	0.07739 (15)	0.31183 (13)	0.0325 (5)
H22	0.4213	0.0604	0.2745	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.02644 (9)	0.02137 (9)	0.02156 (9)	−0.00327 (6)	0.00677 (6)	0.00066 (6)
Cl1	0.0661 (4)	0.0244 (3)	0.0403 (3)	−0.0008 (3)	0.0178 (3)	−0.0036 (2)
Cl2	0.0465 (3)	0.0371 (3)	0.0281 (3)	−0.0135 (2)	0.0126 (2)	0.0043 (2)
P1	0.0270 (3)	0.0234 (3)	0.0196 (2)	−0.0033 (2)	0.00651 (19)	0.00029 (19)
N1	0.0253 (8)	0.0235 (8)	0.0218 (8)	−0.0011 (7)	0.0062 (6)	0.0011 (7)
C1	0.0313 (10)	0.0252 (10)	0.0247 (10)	0.0031 (8)	0.0075 (8)	0.0007 (8)
C2	0.0386 (12)	0.0347 (12)	0.0215 (10)	0.0043 (10)	0.0103 (9)	0.0026 (9)
C3	0.0327 (11)	0.0361 (12)	0.0273 (11)	0.0065 (9)	0.0148 (9)	0.0089 (9)
C4	0.0256 (10)	0.0276 (10)	0.0279 (11)	0.0037 (8)	0.0089 (8)	0.0078 (8)
C5	0.0249 (10)	0.0320 (11)	0.0377 (12)	−0.0006 (9)	0.0106 (9)	0.0096 (9)
C6	0.0271 (10)	0.0286 (11)	0.0394 (13)	−0.0060 (9)	0.0034 (9)	0.0062 (9)
C7	0.0299 (10)	0.0285 (11)	0.0285 (11)	−0.0026 (9)	0.0037 (8)	0.0009 (9)
C8	0.0242 (10)	0.0249 (10)	0.0244 (10)	−0.0014 (8)	0.0061 (8)	0.0037 (8)
C9	0.0228 (9)	0.0223 (9)	0.0236 (10)	0.0011 (8)	0.0060 (7)	0.0038 (8)
C10	0.0394 (13)	0.0378 (13)	0.0252 (12)	−0.0055 (10)	0.0049 (9)	−0.0021 (9)
C11	0.0292 (10)	0.0283 (10)	0.0247 (10)	−0.0004 (8)	0.0110 (8)	0.0039 (8)
C12	0.0313 (11)	0.0362 (12)	0.0348 (12)	−0.0044 (10)	0.0112 (9)	0.0020 (10)
C13	0.0300 (11)	0.0514 (16)	0.0405 (14)	0.0025 (11)	0.0119 (10)	0.0120 (12)
C14	0.0473 (14)	0.0491 (16)	0.0450 (15)	0.0180 (12)	0.0249 (12)	0.0143 (12)
C15	0.0608 (16)	0.0334 (13)	0.0396 (14)	0.0096 (12)	0.0250 (12)	0.0037 (11)
C16	0.0408 (12)	0.0312 (12)	0.0302 (12)	0.0009 (10)	0.0128 (9)	−0.0003 (9)
C17	0.0327 (11)	0.0252 (10)	0.0217 (10)	−0.0050 (8)	0.0068 (8)	0.0008 (8)
C18	0.0418 (13)	0.0364 (12)	0.0272 (11)	0.0009 (10)	0.0122 (9)	0.0004 (10)
C19	0.0567 (15)	0.0411 (14)	0.0244 (12)	−0.0079 (12)	0.0145 (10)	−0.0019 (10)
C20	0.0528 (15)	0.0378 (13)	0.0218 (11)	−0.0103 (11)	0.0006 (10)	0.0043 (10)
C21	0.0358 (12)	0.0373 (13)	0.0347 (13)	−0.0025 (10)	0.0012 (10)	0.0072 (10)
C22	0.0351 (11)	0.0324 (12)	0.0294 (12)	−0.0014 (9)	0.0095 (9)	0.0020 (9)

Geometric parameters (Å, º) top

Pd1—N1	2.0971 (17)	C10—H10B	0.9800
Pd1—P1	2.1910 (5)	C10—H10C	0.9800
Pd1—Cl2	2.2823 (6)	C11—C16	1.391 (3)
Pd1—Cl1	2.3742 (6)	C11—C12	1.401 (3)
P1—C11	1.799 (2)	C12—C13	1.386 (3)
P1—C8	1.800 (2)	C12—H12	0.9500
P1—C17	1.808 (2)	C13—C14	1.368 (4)
N1—C1	1.333 (3)	C13—H13	0.9500
N1—C9	1.390 (3)	C14—C15	1.390 (4)
C1—C2	1.413 (3)	C14—H14	0.9500
C1—C10	1.492 (3)	C15—C16	1.384 (3)
C2—C3	1.351 (3)	C15—H15	0.9500
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.410 (3)	C17—C18	1.384 (3)
C3—H3	0.9500	C17—C22	1.391 (3)
C4—C9	1.406 (3)	C18—C19	1.401 (3)
C4—C5	1.420 (3)	C18—H18	0.9500
C5—C6	1.359 (3)	C19—C20	1.358 (4)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.403 (3)	C20—C21	1.379 (4)
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.380 (3)	C21—C22	1.384 (3)
C7—H7	0.9500	C21—H21	0.9500
C8—C9	1.410 (3)	C22—H22	0.9500
C10—H10A	0.9800

N1—Pd1—P1	83.52 (5)	C1—C10—H10A	109.5
N1—Pd1—Cl2	171.32 (5)	C1—C10—H10B	109.5
P1—Pd1—Cl2	88.25 (2)	H10A—C10—H10B	109.5
N1—Pd1—Cl1	98.30 (5)	C1—C10—H10C	109.5
P1—Pd1—Cl1	166.74 (2)	H10A—C10—H10C	109.5
Cl2—Pd1—Cl1	90.34 (2)	H10B—C10—H10C	109.5
C11—P1—C8	105.50 (10)	C16—C11—C12	120.1 (2)
C11—P1—C17	109.64 (10)	C16—C11—P1	120.69 (17)
C8—P1—C17	106.13 (10)	C12—C11—P1	118.75 (17)
C11—P1—Pd1	117.25 (7)	C13—C12—C11	120.5 (2)
C8—P1—Pd1	99.48 (7)	C13—C12—H12	119.8
C17—P1—Pd1	116.99 (7)	C11—C12—H12	119.8
C1—N1—C9	118.82 (18)	C14—C13—C12	119.2 (2)
C1—N1—Pd1	126.37 (14)	C14—C13—H13	120.4
C9—N1—Pd1	114.50 (13)	C12—C13—H13	120.4
N1—C1—C2	120.5 (2)	C13—C14—C15	120.7 (2)
N1—C1—C10	120.52 (19)	C13—C14—H14	119.7
C2—C1—C10	118.9 (2)	C15—C14—H14	119.7
C3—C2—C1	120.9 (2)	C16—C15—C14	121.1 (2)
C3—C2—H2	119.6	C16—C15—H15	119.5
C1—C2—H2	119.6	C14—C15—H15	119.5
C2—C3—C4	119.7 (2)	C15—C16—C11	118.5 (2)
C2—C3—H3	120.1	C15—C16—H16	120.8
C4—C3—H3	120.1	C11—C16—H16	120.8
C9—C4—C3	117.4 (2)	C18—C17—C22	119.1 (2)
C9—C4—C5	118.5 (2)	C18—C17—P1	122.53 (17)
C3—C4—C5	124.0 (2)	C22—C17—P1	118.19 (16)
C6—C5—C4	121.4 (2)	C17—C18—C19	119.3 (2)
C6—C5—H5	119.3	C17—C18—H18	120.4
C4—C5—H5	119.3	C19—C18—H18	120.4
C5—C6—C7	119.9 (2)	C20—C19—C18	121.1 (2)
C5—C6—H6	120.1	C20—C19—H19	119.5
C7—C6—H6	120.1	C18—C19—H19	119.5
C8—C7—C6	120.3 (2)	C19—C20—C21	120.1 (2)
C8—C7—H7	119.9	C19—C20—H20	119.9
C6—C7—H7	119.9	C21—C20—H20	119.9
C7—C8—C9	120.40 (19)	C20—C21—C22	119.7 (2)
C7—C8—P1	124.94 (17)	C20—C21—H21	120.2
C9—C8—P1	114.22 (15)	C22—C21—H21	120.2
N1—C9—C4	121.63 (19)	C21—C22—C17	120.8 (2)
N1—C9—C8	118.93 (18)	C21—C22—H22	119.6
C4—C9—C8	119.37 (19)	C17—C22—H22	119.6

C9—N1—C1—C2	11.2 (3)	C7—C8—C9—C4	−1.4 (3)
Pd1—N1—C1—C2	−162.19 (16)	P1—C8—C9—C4	171.46 (15)
C9—N1—C1—C10	−165.95 (19)	C8—P1—C11—C16	−66.1 (2)
Pd1—N1—C1—C10	20.7 (3)	C17—P1—C11—C16	47.8 (2)
N1—C1—C2—C3	−5.1 (3)	Pd1—P1—C11—C16	−175.63 (15)
C10—C1—C2—C3	172.1 (2)	C8—P1—C11—C12	106.50 (18)
C1—C2—C3—C4	−3.3 (3)	C17—P1—C11—C12	−139.61 (17)
C2—C3—C4—C9	5.1 (3)	Pd1—P1—C11—C12	−3.1 (2)
C2—C3—C4—C5	−174.3 (2)	C16—C11—C12—C13	0.1 (3)
C9—C4—C5—C6	−2.6 (3)	P1—C11—C12—C13	−172.52 (18)
C3—C4—C5—C6	176.8 (2)	C11—C12—C13—C14	−0.2 (4)
C4—C5—C6—C7	−0.5 (3)	C12—C13—C14—C15	0.3 (4)
C5—C6—C7—C8	2.6 (3)	C13—C14—C15—C16	−0.4 (4)
C6—C7—C8—C9	−1.7 (3)	C14—C15—C16—C11	0.3 (4)
C6—C7—C8—P1	−173.74 (17)	C12—C11—C16—C15	−0.1 (3)
C11—P1—C8—C7	74.4 (2)	P1—C11—C16—C15	172.32 (18)
C17—P1—C8—C7	−41.9 (2)	C11—P1—C17—C18	20.9 (2)
Pd1—P1—C8—C7	−163.70 (17)	C8—P1—C17—C18	134.36 (19)
C11—P1—C8—C9	−98.03 (17)	Pd1—P1—C17—C18	−115.78 (18)
C17—P1—C8—C9	145.66 (15)	C11—P1—C17—C22	−164.51 (17)
Pd1—P1—C8—C9	23.84 (16)	C8—P1—C17—C22	−51.0 (2)
C1—N1—C9—C4	−9.3 (3)	Pd1—P1—C17—C22	58.83 (19)
Pd1—N1—C9—C4	164.82 (15)	C22—C17—C18—C19	1.3 (3)
C1—N1—C9—C8	167.77 (19)	P1—C17—C18—C19	175.92 (18)
Pd1—N1—C9—C8	−18.1 (2)	C17—C18—C19—C20	−2.2 (4)
C3—C4—C9—N1	1.1 (3)	C18—C19—C20—C21	1.3 (4)
C5—C4—C9—N1	−179.45 (18)	C19—C20—C21—C22	0.5 (4)
C3—C4—C9—C8	−175.94 (19)	C20—C21—C22—C17	−1.3 (4)
C5—C4—C9—C8	3.5 (3)	C18—C17—C22—C21	0.4 (3)
C7—C8—C9—N1	−178.54 (19)	P1—C17—C22—C21	−174.44 (18)
P1—C8—C9—N1	−5.7 (2)

Dichlorido[8-(diphenylphosphanyl)-2-phenylquinoline-κ²N</i.,P]palladium(II) (complex2) top

Crystal data top

[PdCl₂(C₂₇H₂₀NP)]	Z = 2
M_r = 566.71	F(000) = 568
Triclinic, P1	D_x = 1.646 Mg m⁻³
a = 9.6582 (13) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.8765 (14) Å	Cell parameters from 9246 reflections
c = 13.0748 (14) Å	θ = 3.0–27.5°
α = 102.011 (4)°	µ = 1.13 mm⁻¹
β = 90.426 (4)°	T = 188 K
γ = 109.827 (4)°	Block, yellow
V = 1143.4 (3) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	5194 independent reflections
Radiation source: fine-focus sealed tube	4682 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: numerical (NUMABS; Rigaku, 1999)	h = −10→12
T_min = 0.640, T_max = 0.797	k = −12→12
11339 measured reflections	l = −16→16

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0323P)² + 0.2021P] where P = (F_o² + 2F_c²)/3
5192 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.59 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
Pd1	0.25082 (2)	1.07058 (2)	0.24836 (2)	0.02194 (6)
Cl1	0.43029 (5)	1.29486 (5)	0.34148 (4)	0.02876 (11)
Cl2	0.24428 (6)	1.16677 (6)	0.10529 (4)	0.03346 (12)
P1	0.13193 (5)	0.84625 (6)	0.15446 (4)	0.02330 (11)
N1	0.24296 (17)	0.96063 (18)	0.36894 (12)	0.0247 (3)
C1	0.2588 (2)	1.0232 (2)	0.47079 (15)	0.0286 (4)
C2	0.3092 (2)	0.9587 (3)	0.54451 (16)	0.0352 (5)
H2	0.3254	1.0066	0.6168	0.042*
C3	0.3343 (2)	0.8301 (3)	0.51319 (16)	0.0358 (5)
H3	0.3758	0.7927	0.5622	0.043*
C4	0.2985 (2)	0.7512 (2)	0.40669 (16)	0.0307 (4)
C5	0.3080 (2)	0.6111 (3)	0.36724 (18)	0.0363 (5)
H5	0.3435	0.5647	0.4130	0.044*
C6	0.2671 (2)	0.5404 (3)	0.26407 (19)	0.0380 (5)
H6	0.2758	0.4465	0.2386	0.046*
C7	0.2116 (2)	0.6075 (2)	0.19524 (17)	0.0332 (5)
H7	0.1802	0.5566	0.1243	0.040*
C8	0.2030 (2)	0.7453 (2)	0.23036 (15)	0.0263 (4)
C9	0.2492 (2)	0.8205 (2)	0.33623 (15)	0.0258 (4)
C10	0.2157 (2)	1.1546 (2)	0.50524 (15)	0.0295 (4)
C11	0.0945 (2)	1.1650 (2)	0.45270 (16)	0.0323 (4)
H11	0.0402	1.0879	0.3954	0.039*
C12	0.0535 (3)	1.2877 (3)	0.48423 (18)	0.0404 (5)
H12	−0.0279	1.2952	0.4476	0.049*
C13	0.1302 (3)	1.3993 (3)	0.56847 (19)	0.0467 (6)
H13	0.1011	1.4829	0.5901	0.056*
C14	0.2493 (3)	1.3890 (3)	0.62121 (18)	0.0452 (6)
H14	0.3026	1.4663	0.6788	0.054*
C15	0.2915 (2)	1.2678 (3)	0.59103 (16)	0.0371 (5)
H15	0.3725	1.2609	0.6287	0.045*
C16	0.1809 (2)	0.8010 (2)	0.02145 (15)	0.0259 (4)
C17	0.3276 (2)	0.8225 (2)	0.00430 (17)	0.0353 (5)
H17	0.3998	0.8545	0.0622	0.042*
C18	0.3692 (3)	0.7974 (3)	−0.09724 (19)	0.0414 (5)
H18	0.4695	0.8110	−0.1090	0.050*
C19	0.2635 (3)	0.7524 (3)	−0.18145 (17)	0.0399 (5)
H19	0.2919	0.7352	−0.2510	0.048*
C20	0.1189 (3)	0.7325 (3)	−0.16542 (16)	0.0373 (5)
H20	0.0476	0.7019	−0.2238	0.045*
C21	0.0756 (2)	0.7571 (2)	−0.06359 (15)	0.0294 (4)
H21	−0.0248	0.7440	−0.0524	0.035*
C22	−0.0677 (2)	0.7813 (2)	0.14853 (14)	0.0242 (4)
C23	−0.1542 (2)	0.6327 (2)	0.12208 (16)	0.0332 (5)
H23	−0.1087	0.5599	0.1105	0.040*
C24	−0.3069 (3)	0.5900 (3)	0.11247 (18)	0.0415 (5)
H24	−0.3660	0.4882	0.0948	0.050*
C25	−0.3732 (2)	0.6962 (3)	0.12869 (17)	0.0387 (5)
H25	−0.4778	0.6668	0.1215	0.046*
C26	−0.2891 (2)	0.8431 (3)	0.15501 (16)	0.0343 (5)
H26	−0.3355	0.9151	0.1665	0.041*
C27	−0.1357 (2)	0.8872 (2)	0.16492 (15)	0.0283 (4)
H27	−0.0774	0.9893	0.1828	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.02264 (9)	0.02275 (9)	0.02375 (9)	0.01079 (6)	0.00033 (5)	0.00750 (6)
Cl1	0.0271 (2)	0.0258 (3)	0.0334 (2)	0.00800 (19)	−0.00090 (17)	0.00894 (18)
Cl2	0.0398 (3)	0.0379 (3)	0.0305 (3)	0.0188 (2)	−0.00031 (19)	0.0154 (2)
P1	0.0233 (3)	0.0241 (3)	0.0258 (2)	0.0119 (2)	0.00061 (17)	0.00659 (18)
N1	0.0238 (8)	0.0290 (9)	0.0236 (8)	0.0101 (7)	0.0007 (6)	0.0094 (6)
C1	0.0221 (10)	0.0328 (11)	0.0306 (10)	0.0069 (8)	0.0027 (7)	0.0108 (8)
C2	0.0312 (12)	0.0494 (14)	0.0277 (10)	0.0127 (10)	0.0002 (8)	0.0168 (9)
C3	0.0289 (11)	0.0514 (14)	0.0353 (11)	0.0155 (10)	0.0012 (8)	0.0247 (10)
C4	0.0226 (10)	0.0373 (12)	0.0399 (11)	0.0133 (9)	0.0051 (8)	0.0205 (9)
C5	0.0278 (11)	0.0397 (13)	0.0532 (14)	0.0174 (10)	0.0063 (9)	0.0265 (10)
C6	0.0337 (12)	0.0306 (12)	0.0593 (14)	0.0185 (10)	0.0079 (10)	0.0185 (10)
C7	0.0319 (12)	0.0304 (12)	0.0416 (12)	0.0156 (9)	0.0028 (8)	0.0098 (9)
C8	0.0243 (10)	0.0252 (10)	0.0333 (10)	0.0113 (8)	0.0026 (7)	0.0103 (8)
C9	0.0202 (10)	0.0280 (10)	0.0343 (10)	0.0110 (8)	0.0044 (7)	0.0137 (8)
C10	0.0280 (11)	0.0336 (11)	0.0256 (10)	0.0073 (9)	0.0067 (7)	0.0097 (8)
C11	0.0298 (11)	0.0328 (12)	0.0333 (11)	0.0096 (9)	0.0053 (8)	0.0074 (8)
C12	0.0358 (13)	0.0418 (14)	0.0495 (13)	0.0179 (11)	0.0133 (10)	0.0148 (10)
C13	0.0548 (16)	0.0330 (13)	0.0522 (14)	0.0156 (12)	0.0187 (11)	0.0083 (10)
C14	0.0531 (16)	0.0355 (13)	0.0358 (12)	0.0040 (11)	0.0104 (10)	0.0034 (9)
C15	0.0349 (12)	0.0411 (13)	0.0290 (11)	0.0055 (10)	0.0037 (8)	0.0073 (9)
C16	0.0278 (10)	0.0238 (10)	0.0289 (10)	0.0129 (8)	0.0035 (7)	0.0054 (7)
C17	0.0281 (11)	0.0368 (13)	0.0430 (12)	0.0150 (10)	0.0037 (8)	0.0067 (9)
C18	0.0336 (13)	0.0388 (13)	0.0566 (15)	0.0172 (10)	0.0203 (10)	0.0126 (10)
C19	0.0546 (15)	0.0323 (12)	0.0373 (12)	0.0196 (11)	0.0190 (10)	0.0091 (9)
C20	0.0477 (14)	0.0367 (13)	0.0286 (11)	0.0163 (11)	0.0048 (9)	0.0069 (9)
C21	0.0299 (11)	0.0307 (11)	0.0315 (10)	0.0141 (9)	0.0045 (8)	0.0090 (8)
C22	0.0236 (10)	0.0295 (10)	0.0225 (9)	0.0111 (8)	0.0028 (7)	0.0087 (7)
C23	0.0337 (12)	0.0301 (12)	0.0393 (11)	0.0147 (9)	0.0030 (8)	0.0091 (9)
C24	0.0353 (13)	0.0332 (13)	0.0512 (14)	0.0048 (10)	0.0013 (10)	0.0115 (10)
C25	0.0241 (11)	0.0519 (15)	0.0429 (12)	0.0123 (10)	0.0031 (8)	0.0184 (10)
C26	0.0321 (12)	0.0459 (14)	0.0342 (11)	0.0230 (10)	0.0043 (8)	0.0127 (9)
C27	0.0292 (11)	0.0300 (11)	0.0288 (10)	0.0132 (9)	0.0010 (7)	0.0085 (8)

Geometric parameters (Å, º) top

Pd1—N1	2.0806 (15)	C12—H12	0.9500
Pd1—P1	2.2036 (6)	C13—C14	1.380 (4)
Pd1—Cl2	2.2769 (5)	C13—H13	0.9500
Pd1—Cl1	2.3738 (6)	C14—C15	1.376 (4)
P1—C22	1.8094 (19)	C14—H14	0.9500
P1—C16	1.8112 (19)	C15—H15	0.9500
P1—C8	1.821 (2)	C16—C17	1.387 (3)
N1—C1	1.330 (2)	C16—C21	1.394 (3)
N1—C9	1.383 (3)	C17—C18	1.387 (3)
C1—C2	1.425 (3)	C17—H17	0.9500
C1—C10	1.479 (3)	C18—C19	1.387 (3)
C2—C3	1.354 (3)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.367 (3)
C3—C4	1.423 (3)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.396 (3)
C4—C5	1.406 (3)	C20—H20	0.9500
C4—C9	1.422 (3)	C21—H21	0.9500
C5—C6	1.370 (3)	C22—C23	1.388 (3)
C5—H5	0.9500	C22—C27	1.395 (3)
C6—C7	1.420 (3)	C23—C24	1.387 (3)
C6—H6	0.9500	C23—H23	0.9500
C7—C8	1.374 (3)	C24—C25	1.385 (3)
C7—H7	0.9500	C24—H24	0.9500
C8—C9	1.416 (3)	C25—C26	1.368 (3)
C10—C15	1.398 (3)	C25—H25	0.9500
C10—C11	1.398 (3)	C26—C27	1.392 (3)
C11—C12	1.383 (3)	C26—H26	0.9500
C11—H11	0.9500	C27—H27	0.9500
C12—C13	1.380 (3)

N1—Pd1—P1	83.24 (5)	C13—C12—C11	120.5 (2)
N1—Pd1—Cl2	173.78 (5)	C13—C12—H12	119.8
P1—Pd1—Cl2	90.56 (2)	C11—C12—H12	119.8
N1—Pd1—Cl1	94.56 (5)	C12—C13—C14	119.8 (2)
P1—Pd1—Cl1	165.930 (19)	C12—C13—H13	120.1
Cl2—Pd1—Cl1	91.57 (2)	C14—C13—H13	120.1
C22—P1—C16	106.75 (9)	C15—C14—C13	120.5 (2)
C22—P1—C8	110.11 (9)	C15—C14—H14	119.7
C16—P1—C8	106.83 (9)	C13—C14—H14	119.7
C22—P1—Pd1	117.05 (7)	C14—C15—C10	120.3 (2)
C16—P1—Pd1	117.40 (7)	C14—C15—H15	119.9
C8—P1—Pd1	97.85 (7)	C10—C15—H15	119.9
C1—N1—C9	119.93 (16)	C17—C16—C21	119.90 (18)
C1—N1—Pd1	124.98 (14)	C17—C16—P1	119.09 (15)
C9—N1—Pd1	113.93 (11)	C21—C16—P1	120.78 (15)
N1—C1—C2	119.8 (2)	C18—C17—C16	120.1 (2)
N1—C1—C10	118.68 (17)	C18—C17—H17	119.9
C2—C1—C10	121.43 (18)	C16—C17—H17	119.9
C3—C2—C1	121.03 (19)	C17—C18—C19	119.6 (2)
C3—C2—H2	119.5	C17—C18—H18	120.2
C1—C2—H2	119.5	C19—C18—H18	120.2
C2—C3—C4	119.82 (18)	C20—C19—C18	120.7 (2)
C2—C3—H3	120.1	C20—C19—H19	119.7
C4—C3—H3	120.1	C18—C19—H19	119.7
C5—C4—C3	124.78 (19)	C19—C20—C21	120.2 (2)
C5—C4—C9	118.47 (19)	C19—C20—H20	119.9
C3—C4—C9	116.74 (19)	C21—C20—H20	119.9
C6—C5—C4	121.20 (19)	C16—C21—C20	119.4 (2)
C6—C5—H5	119.4	C16—C21—H21	120.3
C4—C5—H5	119.4	C20—C21—H21	120.3
C5—C6—C7	120.0 (2)	C23—C22—C27	119.44 (19)
C5—C6—H6	120.0	C23—C22—P1	122.85 (16)
C7—C6—H6	120.0	C27—C22—P1	117.58 (15)
C8—C7—C6	120.6 (2)	C24—C23—C22	120.2 (2)
C8—C7—H7	119.7	C24—C23—H23	119.9
C6—C7—H7	119.7	C22—C23—H23	119.9
C7—C8—C9	119.58 (17)	C25—C24—C23	119.9 (2)
C7—C8—P1	126.59 (15)	C25—C24—H24	120.1
C9—C8—P1	113.81 (14)	C23—C24—H24	120.1
N1—C9—C8	118.45 (16)	C26—C25—C24	120.5 (2)
N1—C9—C4	121.43 (17)	C26—C25—H25	119.8
C8—C9—C4	120.11 (18)	C24—C25—H25	119.8
C15—C10—C11	118.9 (2)	C25—C26—C27	120.2 (2)
C15—C10—C1	121.50 (19)	C25—C26—H26	119.9
C11—C10—C1	119.55 (18)	C27—C26—H26	119.9
C12—C11—C10	120.0 (2)	C26—C27—C22	119.9 (2)
C12—C11—H11	120.0	C26—C27—H27	120.1
C10—C11—H11	120.0	C22—C27—H27	120.1

C9—N1—C1—C2	11.7 (3)	C15—C10—C11—C12	1.6 (3)
Pd1—N1—C1—C2	−155.23 (15)	C1—C10—C11—C12	−179.87 (19)
C9—N1—C1—C10	−165.13 (17)	C10—C11—C12—C13	−1.0 (3)
Pd1—N1—C1—C10	28.0 (2)	C11—C12—C13—C14	0.5 (4)
N1—C1—C2—C3	−3.4 (3)	C12—C13—C14—C15	−0.6 (4)
C10—C1—C2—C3	173.3 (2)	C13—C14—C15—C10	1.2 (3)
C1—C2—C3—C4	−5.3 (3)	C11—C10—C15—C14	−1.7 (3)
C2—C3—C4—C5	−174.4 (2)	C1—C10—C15—C14	179.83 (19)
C2—C3—C4—C9	5.5 (3)	C22—P1—C16—C17	−172.40 (17)
C3—C4—C5—C6	178.0 (2)	C8—P1—C16—C17	−54.62 (19)
C9—C4—C5—C6	−1.8 (3)	Pd1—P1—C16—C17	53.89 (19)
C4—C5—C6—C7	−1.0 (3)	C22—P1—C16—C21	13.03 (19)
C5—C6—C7—C8	2.1 (3)	C8—P1—C16—C21	130.82 (17)
C6—C7—C8—C9	−0.3 (3)	Pd1—P1—C16—C21	−120.67 (16)
C6—C7—C8—P1	−178.71 (17)	C21—C16—C17—C18	−1.4 (3)
C22—P1—C8—C7	80.9 (2)	P1—C16—C17—C18	−175.99 (17)
C16—P1—C8—C7	−34.6 (2)	C16—C17—C18—C19	0.8 (3)
Pd1—P1—C8—C7	−156.42 (18)	C17—C18—C19—C20	0.0 (4)
C22—P1—C8—C9	−97.56 (16)	C18—C19—C20—C21	−0.1 (4)
C16—P1—C8—C9	146.89 (14)	C17—C16—C21—C20	1.2 (3)
Pd1—P1—C8—C9	25.08 (15)	P1—C16—C21—C20	175.74 (16)
C1—N1—C9—C8	167.48 (18)	C19—C20—C21—C16	−0.5 (3)
Pd1—N1—C9—C8	−24.2 (2)	C16—P1—C22—C23	66.97 (18)
C1—N1—C9—C4	−11.5 (3)	C8—P1—C22—C23	−48.63 (19)
Pd1—N1—C9—C4	156.78 (15)	Pd1—P1—C22—C23	−159.13 (14)
C7—C8—C9—N1	178.38 (19)	C16—P1—C22—C27	−108.83 (15)
P1—C8—C9—N1	−3.0 (2)	C8—P1—C22—C27	135.57 (15)
C7—C8—C9—C4	−2.6 (3)	Pd1—P1—C22—C27	25.07 (16)
P1—C8—C9—C4	176.01 (15)	C27—C22—C23—C24	−0.2 (3)
C5—C4—C9—N1	−177.37 (18)	P1—C22—C23—C24	−175.97 (16)
C3—C4—C9—N1	2.8 (3)	C22—C23—C24—C25	0.4 (3)
C5—C4—C9—C8	3.7 (3)	C23—C24—C25—C26	−0.5 (3)
C3—C4—C9—C8	−176.20 (18)	C24—C25—C26—C27	0.5 (3)
N1—C1—C10—C15	−146.2 (2)	C25—C26—C27—C22	−0.3 (3)
C2—C1—C10—C15	37.0 (3)	C23—C22—C27—C26	0.2 (3)
N1—C1—C10—C11	35.3 (3)	P1—C22—C27—C26	176.17 (15)
C2—C1—C10—C11	−141.5 (2)

Funding information

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

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Volume 77| Part 1| January 2021| Pages 52-57

https://doi.org/10.1107/S2056989020016096

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

Crystal and mol­ecular structures of di­chlorido­palladium(II) containing 2-methyl- or 2-phenyl-8-(diphenyphosphan­yl)quinoline

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

Crystal and molecular structures of dichloridopalladium(II) containing 2-methyl- or 2-phenyl-8-(diphenyphosphanyl)quinoline

3. Supramolecular features