trans-[1,3-Bis(2,4,6-trimethyl­phenyl)­imidazolidin-2-yl­idene]­dichlorido(triphenyl­phosphine-κP)palladium(II)

The title complex, [PdCl₂(C₂₁H₂₆N₂)(C₁₈H₁₅P)], shows slightly distorted square-planar coordination around the Pd^II metal centre. The Pd—C bond distance between the N-heterocyclic ligand and the metal atom is 2.028 (5) Å. The dihedral angle between the two trimethyl­phenyl ring planes is 36.9 (2)°.

S1. Comment

There are relatively few homogeneous transition metal catalysts where both steric and electronic effects can be finely controlled by small changes of ligand structure within the series. N-Heterocyclic carbenes (NHCs), in conjunction with widely used phosphines, have broadened the scope for the screening of ligands for desired properties (Bourissou et al. 2000; Türkmen et al. 2006). NHC ligands in metal complexes are known to have electronic similarities with trialkylphosphines but appear to be stronger coordinating ligands which undergo little to no dissociation from the metal in solution (Lappert, 1975). In contrast with most metal–carbene complexes which have found extensive application in organic synthesis and which incorporate the carbene moiety into the organic product (Zaragoza Dörwald, 1998), NHCs act as non-participating ligands in catalytic processes and are not consumed (Bourissou et al. 2000; Türkmen et al. 2006). Here, we describe the preparation and characterization of the title palladium–NHC complex, (IV) (see scheme).

A trans coordination of the carbene group and one phosphine group to the Pd^II centre is found in the crystal structure of (IV), as shown in Fig. 1. The coordination of the ligands is not exactly planar, the deviations of ligating atoms Cl1, Cl2, P1 and C1 from the plane through these atoms and the Pd atom being 0.074 (1), 0.079 (1), -0.070 (1) and -0.078 (2) Å, respectively. The dihedral angle between the Pd1/Cl1/Cl2/P1/C1 coordination plane, formed by the slightly distorted square-planar coordination of the Pd^II metal centre, and the carbene ring is 74.90 (17)°, as reported for similar N-heterocyclic carbene complexes (Gökçe, Gülcemal et al., 2006; Gökçe, Günay et al., 2006). The Pd—C bond distance between the N-heterocyclic ligand and the metal atom is 2.028 (5) Å, comparable with that in other palladium(II)–NHC complexes (Gökçe et al., 2004; Liu et al., 2003; Magill et al., 2001).

The bond angles at the Pd atom involving trans pairs of substituents deviate from the expected value of 180°, being 173.87 (15)° for the C1—Pd1—P1 angle and 175.71 (6)° for the Cl1—Pd—Cl2 angle, and this distortion of the bond angles at Pd may be attributed to steric interaction between the Cl atoms and the aromatic rings. There are two short intramolecular C—H···Cl contacts (Table 2), both of them involving methyl groups at the 2-position.

Although both C—N bonds in the NHC ring of (IV) are single bonds, their distances are different (Table 1), as observed in similar complexes (Karabıyık et al., 2006; Karabıyık, Kılınçarslan, Aygün, Çetinkaya & Büyükgüngör, 2007; Karabıyık, Kılınçarslan, Aygün, Çetinkaya & García-Granda, 2007; Gökçe et al., 2004; Gökçe, Gülcemal et al., 2006 OR Gökçe, Günay et al., 2006?). The bond distances between the carbene C atom bonded to Pd and the N atoms in the NHC ring are shorter than the other C—N bond distances (Table 1). This is possibly indicative of a greater partial double-bond character due to partial electron donation by N to the carbene C atom donor (Herrmann et al., 2001; Fröhlich et al., 1997). Theoretical study also indicates that the stability of these carbenes is due to electron donation from the nitrogen lone pairs into the formally vacant p(π) orbital of the carbene C atom (Karabıyık et al., 2005). The Pd—P bond distance is also similar to those reported previously (Aupers et al., 2000; McCrindle et al., 2000; Gökçe et al., 2004).

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Related literature

For related literature, see: Aupers et al. (2000); Bourissou et al. (2000); Fröhlich et al. (1997); Gökçe et al. (2004); Gökçe, Gülcemal, Aygün, Çetinkaya & Büyükgüngör (2006); Gökçe, Günay, Aygün, Çetinkaya & Büyükgüngör (2006); Herrmann et al. (2001); Karabıyık, Kılınçarslan, Aygün, Çetinkaya & Büyükgüngör (2005, 2006, 2007); Karabıyık, Kılınçarslan, Aygün, Çetinkaya & García-Granda (2007); Lappert (1975); Liu et al. (2003); Magill et al. (2001); McCrindle et al. (2000); Türkmen et al. (2006); Zaragoza (1998).

S2. Experimental

A suspension of the salt (III), prepared as indicated in the scheme (0.17 g, 0.5 mmol), and sodium hydride (0.17 g, 0.75 mmol) in tetrahydrofuran (10 ml) was heated under reflux for 4 h. The mixture was cooled to ambient temperature and the volatiles were removed. To the residue was added [PdCl₂(PPh₃)]₂ (0.22 g, 0.25 mmol) and then toluene (5 ml). The mixture was heated under reflux for 4 h, after which it was cooled to ambient temperature and hexane (10 ml) was added. The resulting cream precipitate was collected by filtration and recrystallized from CH₂Cl₂–Et₂O (Ratio?) (yield 0.28 g, 75%; m.p 545–547 K). IR (Medium?): ν(NCN) = 1457 cm^-1; analysis calculated for C₃₉H₄₁Cl₂N₂PPd: C 62.79, H 5.54, N 3,75; found: C, 61.63, H 5,55, N 3.75%; ¹H NMR (CDCl₃, δ, p.p.m.): 2.41 (s, 12H, ortho-CH₃), 2.53 (s, 6H, para-CH₃), 4.00 (s, 4H, Im—H^4,5), 7.30–7.16 (m, 19H, Ar, PPh₃); ¹³C NMR (CDCl₃, δ, p.p.m.): 19.5 (ortho-CH₃), 21.4 (para-CH₃), 51.45 (Im—C^4,5), 127.7 (d, J_C—P = 9.9 Hz, m-C PC₆H₅), 129.4 (Ar), 129.9 (d, J_C—P = 2.3 Hz, p-C PC₆H₅), 130.7 (d, J_C—P = 43.5 Hz, ipso-C PC₆H₅), 135.2 (d, J_C—P = 10.7 Hz, o-C PC₆H₅), 135.6, 137.6, 138.0 (Ar), 197.2 (d, 2J_C—P = 185.3 Hz, C–Pd); ³¹P (CDCl₃, δ, p.p.m.): 20.88.

S3. Refinement

H atoms were treated as riding atoms, with C—H distances of 0.93 Å for aromatic H atoms, 0.96 Å for methyl H atoms and 0.97 Å for methylene H atoms, and with U_iso(H) = 1.2U_eq(C) for aromatic and methylene H, or 1.5U_eq(C) for methyl H. CH₃ groups were allowed to rotate freely around the C—C bond.

Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CRYSDA (Beurskens et al., 1999); data reduction: REFLEX (García-Granda et al., 1999; Lehman & Larsen, 1974; Grant & Gabe, 1978); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular structure of (IV), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

trans-[1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2- ylidene]dichlorido(triphenylphosphine-κP)palladium(II)

Crystal data

[PdCl2(C21H26N2)(C18H15P)]	F(000) = 1536
Mr = 746.01	Dx = 1.377 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 17.418 (3) Å	θ = 10–15°
b = 13.8020 (17) Å	µ = 0.74 mm^−1
c = 14.982 (6) Å	T = 293 K
β = 91.90 (5)°	Plate, yellow
V = 3599.7 (16) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	5215 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 26.0°, θmin = 1.2°
ω/2θ scans	h = 0→21
Absorption correction: analytical (Katayama, 1986)	k = 0→17
Tmin = 0.760, Tmax = 0.782	l = −18→18
7676 measured reflections	3 standard reflections every 60 min
7060 independent reflections	intensity decay: 0.9%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0884P)^2 + 4.1023P] where P = (Fo^2 + 2Fc^2)/3
7060 reflections	(Δ/σ)max = 0.005
410 parameters	Δρmax = 0.75 e Å^−3
0 restraints	Δρmin = −0.93 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.74873 (2)	0.56490 (3)	0.31448 (2)	0.03120 (14)
Cl1	0.65122 (8)	0.65212 (10)	0.37476 (9)	0.0470 (3)
Cl2	0.85270 (9)	0.48125 (12)	0.26254 (10)	0.0558 (4)
P1	0.74802 (8)	0.45245 (9)	0.42941 (8)	0.0356 (3)
N1	0.8056 (2)	0.7157 (3)	0.1847 (3)	0.0407 (10)
N2	0.7018 (3)	0.6434 (4)	0.1367 (3)	0.0474 (12)
C1	0.7520 (3)	0.6513 (4)	0.2052 (3)	0.0366 (11)
C2	0.7919 (4)	0.7570 (5)	0.0946 (4)	0.0551 (16)
H2A	0.8350	0.7446	0.0568	0.066*
H2B	0.7830	0.8263	0.0975	0.066*
C3	0.7215 (4)	0.7050 (5)	0.0606 (4)	0.0613 (11)
H3A	0.6804	0.7501	0.0456	0.074*
H3B	0.7322	0.6663	0.0085	0.074*
C11	0.8646 (3)	0.7544 (4)	0.2441 (4)	0.0422 (12)
C12	0.8444 (3)	0.8236 (4)	0.3071 (4)	0.0469 (13)
C13	0.9026 (4)	0.8602 (5)	0.3647 (4)	0.0544 (15)
H13	0.8900	0.9039	0.4091	0.065*
C14	0.9781 (4)	0.8326 (5)	0.3566 (4)	0.0556 (16)
C15	0.9965 (4)	0.7701 (5)	0.2900 (5)	0.0615 (18)
H15	1.0479	0.7549	0.2828	0.074*
C16	0.9412 (3)	0.7279 (4)	0.2322 (4)	0.0474 (13)
C17	0.7639 (4)	0.8592 (5)	0.3127 (5)	0.0643 (18)
H17A	0.7479	0.8879	0.2568	0.096*
H17B	0.7614	0.9068	0.3593	0.096*
H17C	0.7307	0.8059	0.3258	0.096*
C18	1.0408 (5)	0.8732 (7)	0.4192 (5)	0.082 (2)
H18A	1.0892	0.8711	0.3902	0.123*
H18B	1.0441	0.8351	0.4727	0.123*
H18C	1.0289	0.9391	0.4339	0.123*
C19	0.9639 (4)	0.6604 (6)	0.1599 (5)	0.0663 (18)
H19A	0.9978	0.6932	0.1206	0.099*
H19B	0.9189	0.6393	0.1267	0.099*
H19C	0.9898	0.6052	0.1858	0.099*
C21	0.6355 (3)	0.5811 (4)	0.1327 (3)	0.0438 (13)
C22	0.6434 (4)	0.4855 (5)	0.1051 (4)	0.0544 (15)
C23	0.5771 (4)	0.4291 (5)	0.1005 (4)	0.0623 (18)
H23	0.5812	0.3642	0.0845	0.075*
C24	0.5061 (4)	0.4653 (6)	0.1185 (4)	0.0622 (19)
C25	0.5006 (4)	0.5608 (6)	0.1424 (4)	0.0619 (18)
H25	0.4525	0.5863	0.1539	0.074*
C26	0.5643 (4)	0.6209 (5)	0.1500 (4)	0.0507 (14)
C27	0.7193 (5)	0.4447 (6)	0.0785 (5)	0.077 (2)
H27A	0.7188	0.3755	0.0854	0.116*
H27B	0.7596	0.4718	0.1159	0.116*
H27C	0.7279	0.4606	0.0173	0.116*
C28	0.4352 (5)	0.4013 (7)	0.1099 (5)	0.097 (3)
H28A	0.3912	0.4366	0.1290	0.145*
H28B	0.4425	0.3448	0.1465	0.145*
H28C	0.4273	0.3821	0.0487	0.145*
C29	0.5551 (5)	0.7269 (5)	0.1745 (5)	0.074 (2)
H29A	0.5531	0.7654	0.1211	0.111*
H29B	0.5980	0.7470	0.2119	0.111*
H29C	0.5085	0.7353	0.2059	0.111*
C31	0.8278 (3)	0.4733 (4)	0.5080 (3)	0.0415 (12)
C32	0.8333 (4)	0.4261 (6)	0.5906 (4)	0.0690 (19)
H32	0.7984	0.3776	0.6039	0.083*
C33	0.8911 (5)	0.4514 (7)	0.6532 (5)	0.085 (3)
H33	0.8940	0.4206	0.7084	0.102*
C34	0.9436 (4)	0.5217 (7)	0.6334 (5)	0.081 (3)
H34	0.9820	0.5386	0.6751	0.097*
C35	0.9393 (4)	0.5665 (6)	0.5524 (5)	0.071 (2)
H35	0.9751	0.6139	0.5391	0.085*
C36	0.8818 (3)	0.5422 (5)	0.4891 (4)	0.0519 (15)
H36	0.8800	0.5730	0.4338	0.062*
C41	0.7532 (3)	0.3307 (4)	0.3822 (4)	0.0463 (13)
C42	0.7051 (4)	0.3110 (5)	0.3094 (4)	0.0618 (16)
H42	0.6740	0.3599	0.2853	0.074*
C43	0.7026 (6)	0.2190 (6)	0.2718 (5)	0.084 (2)
H43	0.6691	0.2056	0.2237	0.101*
C44	0.7493 (6)	0.1490 (6)	0.3059 (6)	0.091 (3)
H44	0.7476	0.0871	0.2812	0.110*
C45	0.7995 (5)	0.1683 (5)	0.3768 (6)	0.079 (2)
H45	0.8325	0.1201	0.3982	0.095*
C46	0.8011 (4)	0.2587 (5)	0.4162 (5)	0.0587 (16)
H46	0.8340	0.2711	0.4651	0.070*
C51	0.6656 (3)	0.4433 (4)	0.5016 (3)	0.0397 (11)
C52	0.6093 (4)	0.3743 (5)	0.4916 (4)	0.0613 (17)
H52	0.6134	0.3276	0.4472	0.074*
C53	0.5470 (4)	0.3722 (6)	0.5454 (5)	0.077 (2)
H53	0.5089	0.3258	0.5358	0.093*
C54	0.5407 (4)	0.4384 (5)	0.6132 (4)	0.0623 (17)
H54	0.4990	0.4363	0.6504	0.075*
C55	0.5961 (4)	0.5070 (5)	0.6253 (5)	0.0680 (19)
H55	0.5930	0.5510	0.6721	0.082*
C56	0.6570 (4)	0.5118 (5)	0.5684 (5)	0.0642 (18)
H56	0.6927	0.5616	0.5750	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0329 (2)	0.0357 (2)	0.02520 (19)	0.00034 (16)	0.00433 (13)	0.00267 (15)
Cl1	0.0464 (7)	0.0502 (7)	0.0451 (7)	0.0098 (6)	0.0136 (6)	0.0027 (6)
Cl2	0.0534 (8)	0.0620 (9)	0.0534 (8)	0.0160 (7)	0.0203 (7)	0.0048 (7)
P1	0.0401 (7)	0.0383 (7)	0.0284 (6)	0.0008 (5)	0.0015 (5)	0.0043 (5)
N1	0.041 (2)	0.051 (3)	0.030 (2)	−0.007 (2)	0.0004 (18)	0.0098 (19)
N2	0.051 (3)	0.062 (3)	0.028 (2)	−0.017 (2)	−0.0051 (19)	0.014 (2)
C1	0.036 (3)	0.039 (3)	0.035 (3)	0.001 (2)	0.003 (2)	0.003 (2)
C2	0.060 (4)	0.063 (4)	0.042 (3)	−0.008 (3)	0.003 (3)	0.025 (3)
C3	0.070	0.066	0.047 (3)	−0.027 (3)	−0.011 (3)	0.027 (3)
C11	0.043 (3)	0.043 (3)	0.040 (3)	−0.004 (2)	0.001 (2)	0.006 (2)
C12	0.049 (3)	0.048 (3)	0.044 (3)	−0.002 (3)	0.005 (2)	0.011 (3)
C13	0.067 (4)	0.055 (3)	0.042 (3)	−0.010 (3)	0.005 (3)	0.003 (3)
C14	0.062 (4)	0.066 (4)	0.039 (3)	−0.019 (3)	−0.006 (3)	0.013 (3)
C15	0.041 (3)	0.079 (5)	0.064 (4)	−0.005 (3)	−0.002 (3)	0.027 (4)
C16	0.043 (3)	0.048 (3)	0.052 (3)	0.002 (2)	0.006 (2)	0.009 (3)
C17	0.064 (4)	0.063 (4)	0.067 (4)	0.002 (3)	0.018 (3)	−0.008 (3)
C18	0.083 (5)	0.104 (6)	0.058 (4)	−0.041 (5)	−0.016 (4)	0.012 (4)
C19	0.047 (3)	0.088 (5)	0.065 (4)	0.004 (3)	0.018 (3)	−0.005 (4)
C21	0.048 (3)	0.056 (3)	0.027 (2)	−0.011 (3)	−0.007 (2)	0.007 (2)
C22	0.059 (4)	0.066 (4)	0.038 (3)	−0.007 (3)	−0.005 (3)	−0.006 (3)
C23	0.090 (5)	0.052 (4)	0.044 (3)	−0.017 (4)	−0.011 (3)	−0.005 (3)
C24	0.066 (4)	0.085 (5)	0.036 (3)	−0.033 (4)	−0.006 (3)	0.011 (3)
C25	0.048 (3)	0.093 (5)	0.044 (3)	−0.013 (3)	−0.005 (3)	0.007 (3)
C26	0.056 (4)	0.062 (4)	0.034 (3)	−0.005 (3)	−0.006 (2)	0.005 (3)
C27	0.084 (5)	0.078 (5)	0.070 (5)	0.006 (4)	0.003 (4)	−0.022 (4)
C28	0.093 (6)	0.130 (7)	0.066 (5)	−0.069 (6)	−0.014 (4)	0.023 (5)
C29	0.079 (5)	0.069 (5)	0.074 (5)	0.013 (4)	−0.013 (4)	0.001 (4)
C31	0.046 (3)	0.042 (3)	0.037 (3)	0.013 (2)	−0.003 (2)	−0.005 (2)
C32	0.075 (5)	0.086 (5)	0.045 (4)	0.008 (4)	−0.009 (3)	0.012 (3)
C33	0.099 (6)	0.097 (6)	0.056 (4)	0.038 (5)	−0.036 (4)	−0.023 (4)
C34	0.060 (4)	0.111 (7)	0.070 (5)	0.031 (5)	−0.027 (4)	−0.041 (5)
C35	0.041 (3)	0.085 (5)	0.086 (5)	0.004 (3)	−0.002 (3)	−0.042 (4)
C36	0.037 (3)	0.066 (4)	0.052 (3)	0.005 (3)	0.003 (2)	−0.013 (3)
C41	0.056 (3)	0.046 (3)	0.037 (3)	−0.002 (3)	0.011 (2)	0.003 (2)
C42	0.079 (5)	0.057 (4)	0.049 (4)	−0.001 (3)	0.001 (3)	0.001 (3)
C43	0.126 (7)	0.068 (5)	0.059 (4)	−0.018 (5)	0.015 (5)	−0.028 (4)
C44	0.144 (9)	0.050 (4)	0.082 (6)	−0.013 (5)	0.038 (6)	−0.016 (4)
C45	0.109 (6)	0.043 (4)	0.089 (6)	0.020 (4)	0.033 (5)	0.006 (4)
C46	0.067 (4)	0.050 (3)	0.061 (4)	0.013 (3)	0.012 (3)	0.006 (3)
C51	0.048 (3)	0.043 (3)	0.029 (2)	0.000 (2)	0.004 (2)	0.009 (2)
C52	0.052 (4)	0.081 (5)	0.052 (4)	−0.019 (3)	0.009 (3)	−0.008 (3)
C53	0.057 (4)	0.092 (6)	0.083 (5)	−0.026 (4)	0.015 (4)	−0.003 (5)
C54	0.052 (4)	0.085 (5)	0.051 (4)	0.000 (3)	0.015 (3)	0.013 (4)
C55	0.083 (5)	0.062 (4)	0.061 (4)	−0.004 (4)	0.034 (4)	−0.003 (3)
C56	0.066 (4)	0.063 (4)	0.065 (4)	−0.020 (3)	0.028 (3)	−0.011 (3)

Geometric parameters (Å, º)

Pd1—C1	2.028 (5)	C25—C26	1.387 (9)
Pd1—Cl1	2.2915 (15)	C25—H25	0.9300
Pd1—Cl2	2.3047 (15)	C26—C29	1.519 (9)
Pd1—P1	2.3185 (14)	C27—H27A	0.9600
P1—C31	1.814 (5)	C27—H27B	0.9600
P1—C41	1.827 (6)	C27—H27C	0.9600
P1—C51	1.831 (5)	C28—H28A	0.9600
N1—C1	1.333 (6)	C28—H28B	0.9600
N1—C11	1.439 (7)	C28—H28C	0.9600
N1—C2	1.478 (6)	C29—H29A	0.9600
N2—C1	1.331 (6)	C29—H29B	0.9600
N2—C21	1.440 (7)	C29—H29C	0.9600
N2—C3	1.471 (7)	C31—C36	1.374 (8)
C2—C3	1.495 (8)	C31—C32	1.399 (8)
C2—H2A	0.9700	C32—C33	1.397 (10)
C2—H2B	0.9700	C32—H32	0.9300
C3—H3A	0.9700	C33—C34	1.372 (13)
C3—H3B	0.9700	C33—H33	0.9300
C11—C12	1.396 (8)	C34—C35	1.361 (12)
C11—C16	1.401 (8)	C34—H34	0.9300
C12—C13	1.404 (8)	C35—C36	1.397 (9)
C12—C17	1.491 (8)	C35—H35	0.9300
C13—C14	1.377 (9)	C36—H36	0.9300
C13—H13	0.9300	C41—C42	1.380 (9)
C14—C15	1.365 (9)	C41—C46	1.384 (8)
C14—C18	1.523 (9)	C42—C43	1.390 (9)
C15—C16	1.400 (9)	C42—H42	0.9300
C15—H15	0.9300	C43—C44	1.353 (12)
C16—C19	1.492 (9)	C43—H43	0.9300
C17—H17A	0.9600	C44—C45	1.379 (12)
C17—H17B	0.9600	C44—H44	0.9300
C17—H17C	0.9600	C45—C46	1.381 (10)
C18—H18A	0.9600	C45—H45	0.9300
C18—H18B	0.9600	C46—H46	0.9300
C18—H18C	0.9600	C51—C52	1.372 (8)
C19—H19A	0.9600	C51—C56	1.388 (8)
C19—H19B	0.9600	C52—C53	1.372 (9)
C19—H19C	0.9600	C52—H52	0.9300
C21—C26	1.388 (8)	C53—C54	1.374 (10)
C21—C22	1.391 (9)	C53—H53	0.9300
C22—C23	1.393 (9)	C54—C55	1.360 (10)
C22—C27	1.503 (10)	C54—H54	0.9300
C23—C24	1.369 (10)	C55—C56	1.385 (8)
C23—H23	0.9300	C55—H55	0.9300
C24—C25	1.370 (10)	C56—H56	0.9300
C24—C28	1.520 (9)
C1—Pd1—Cl1	92.89 (15)	C25—C24—C28	121.2 (8)
C1—Pd1—Cl2	88.76 (15)	C24—C25—C26	122.2 (7)
Cl1—Pd1—Cl2	175.71 (6)	C24—C25—H25	118.9
C1—Pd1—P1	173.87 (15)	C26—C25—H25	118.9
Cl1—Pd1—P1	92.10 (6)	C25—C26—C21	117.8 (6)
Cl2—Pd1—P1	86.50 (6)	C25—C26—C29	120.3 (6)
C31—P1—C41	110.5 (3)	C21—C26—C29	121.9 (6)
C31—P1—C51	103.1 (2)	C22—C27—H27A	109.5
C41—P1—C51	102.4 (2)	C22—C27—H27B	109.5
C31—P1—Pd1	110.69 (19)	H27A—C27—H27B	109.5
C41—P1—Pd1	109.08 (18)	C22—C27—H27C	109.5
C51—P1—Pd1	120.58 (17)	H27A—C27—H27C	109.5
C1—N1—C11	126.7 (4)	H27B—C27—H27C	109.5
C1—N1—C2	111.9 (4)	C24—C28—H28A	109.5
C11—N1—C2	120.9 (4)	C24—C28—H28B	109.5
C1—N2—C21	125.9 (4)	H28A—C28—H28B	109.5
C1—N2—C3	112.8 (4)	C24—C28—H28C	109.5
C21—N2—C3	121.3 (4)	H28A—C28—H28C	109.5
N2—C1—N1	108.9 (4)	H28B—C28—H28C	109.5
N2—C1—Pd1	122.7 (4)	C26—C29—H29A	109.5
N1—C1—Pd1	128.1 (4)	C26—C29—H29B	109.5
N1—C2—C3	103.5 (4)	H29A—C29—H29B	109.5
N1—C2—H2A	111.1	C26—C29—H29C	109.5
C3—C2—H2A	111.1	H29A—C29—H29C	109.5
N1—C2—H2B	111.1	H29B—C29—H29C	109.5
C3—C2—H2B	111.1	C36—C31—C32	118.5 (6)
H2A—C2—H2B	109.0	C36—C31—P1	119.4 (4)
N2—C3—C2	102.9 (5)	C32—C31—P1	122.0 (5)
N2—C3—H3A	111.2	C33—C32—C31	120.3 (8)
C2—C3—H3A	111.2	C33—C32—H32	119.8
N2—C3—H3B	111.2	C31—C32—H32	119.8
C2—C3—H3B	111.2	C34—C33—C32	120.1 (8)
H3A—C3—H3B	109.1	C34—C33—H33	119.9
C12—C11—C16	121.8 (5)	C32—C33—H33	119.9
C12—C11—N1	118.7 (5)	C35—C34—C33	119.7 (7)
C16—C11—N1	119.3 (5)	C35—C34—H34	120.1
C11—C12—C13	118.0 (5)	C33—C34—H34	120.1
C11—C12—C17	121.5 (5)	C34—C35—C36	120.9 (8)
C13—C12—C17	120.5 (6)	C34—C35—H35	119.6
C14—C13—C12	121.2 (6)	C36—C35—H35	119.6
C14—C13—H13	119.4	C31—C36—C35	120.4 (7)
C12—C13—H13	119.4	C31—C36—H36	119.8
C15—C14—C13	119.1 (6)	C35—C36—H36	119.8
C15—C14—C18	120.1 (7)	C42—C41—C46	119.6 (6)
C13—C14—C18	120.8 (7)	C42—C41—P1	116.7 (5)
C14—C15—C16	122.8 (6)	C46—C41—P1	123.7 (5)
C14—C15—H15	118.6	C41—C42—C43	120.7 (7)
C16—C15—H15	118.6	C41—C42—H42	119.7
C15—C16—C11	116.8 (6)	C43—C42—H42	119.7
C15—C16—C19	121.1 (6)	C44—C43—C42	119.3 (8)
C11—C16—C19	122.1 (6)	C44—C43—H43	120.4
C12—C17—H17A	109.5	C42—C43—H43	120.4
C12—C17—H17B	109.5	C43—C44—C45	120.7 (7)
H17A—C17—H17B	109.5	C43—C44—H44	119.6
C12—C17—H17C	109.5	C45—C44—H44	119.6
H17A—C17—H17C	109.5	C44—C45—C46	120.6 (8)
H17B—C17—H17C	109.5	C44—C45—H45	119.7
C14—C18—H18A	109.5	C46—C45—H45	119.7
C14—C18—H18B	109.5	C45—C46—C41	119.1 (7)
H18A—C18—H18B	109.5	C45—C46—H46	120.4
C14—C18—H18C	109.5	C41—C46—H46	120.4
H18A—C18—H18C	109.5	C52—C51—C56	117.3 (5)
H18B—C18—H18C	109.5	C52—C51—P1	123.7 (4)
C16—C19—H19A	109.5	C56—C51—P1	118.9 (4)
C16—C19—H19B	109.5	C53—C52—C51	121.7 (7)
H19A—C19—H19B	109.5	C53—C52—H52	119.1
C16—C19—H19C	109.5	C51—C52—H52	119.1
H19A—C19—H19C	109.5	C52—C53—C54	120.4 (7)
H19B—C19—H19C	109.5	C52—C53—H53	119.8
C26—C21—C22	121.8 (5)	C54—C53—H53	119.8
C26—C21—N2	118.5 (5)	C55—C54—C53	119.2 (6)
C22—C21—N2	119.5 (5)	C55—C54—H54	120.4
C21—C22—C23	117.1 (6)	C53—C54—H54	120.4
C21—C22—C27	122.0 (6)	C54—C55—C56	120.4 (7)
C23—C22—C27	120.8 (6)	C54—C55—H55	119.8
C24—C23—C22	122.6 (6)	C56—C55—H55	119.8
C24—C23—H23	118.7	C55—C56—C51	120.9 (6)
C22—C23—H23	118.7	C55—C56—H56	119.5
C23—C24—C25	118.4 (6)	C51—C56—H56	119.5
C23—C24—C28	120.4 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17C···Cl1	0.96	2.65	3.606 (7)	174
C27—H27B···Cl2	0.96	2.69	3.582 (8)	155