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The title complex, chloro(6,6''-dimesityl-2,2':6',2''-ter­pyri­dine)palla­dium(II) tetrachloropalladium(II) dichloromethane tetrasolvate, [PdIICl(dmtpy)]2[PdIICl4]·4CH2Cl2 (dmtpy is 6,6''-dimesityl-2,2':6',2''-ter­pyridine, C33H31N3), was synthesized and the crystal structure of the di­chloro­methane tetra­solvate has been determined. The complex has a distorted square-planar coordination formed by three N atoms and a chloride ion, the distortion caused by the extremely bulky substituted terpyridyl ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008626/fl6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008626/fl6020Isup2.hkl
Contains datablock I

CCDC reference: 214580

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in solvent or counterion
  • R factor = 0.053
  • wR factor = 0.144
  • Data-to-parameter ratio = 17.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 8029 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 8763 Completeness (_total/calc) 91.62% Alert C: < 95% complete PLAT_302 Alert C Anion/Solvent Disorder ....................... 21.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Design of N-chelating ligands with various bulky substituents is an essential approach in developing N-chelating metal catalysis for polymerization. For example, Brookhart and co-workers have reported highly efficient Pd and Ni catalysts with α-diimino ligands for the polymerization of ethylene and α-olefin (Johnson et al., 1995). It was also reported that control of the bulkiness in pyridine bisimino ligands (3 N coordination) contributes to polymerization by their Fe and Co catalysis (Small et al., 1998; Britovsek et al., 1998). We have synthesized a palladium monochloride complex with a bulky terpyridine ligand, namely 6,6''-dimesityl-2,2':6',2''-terpyridine and determined the effect of the steric hindrance of the ligands, which perturbs the metal coordination geometry.

Fig. 1(a) shows the molecular structure. The asymmetric unit consists of one cation of PdII(dmtpy), half of a PdIICl4 anion and two dichloromethanes. Fig. 1(b) shows the cation part of the structure. Pd complex (I) has a distorted square-planar coordination formed by three N atoms and a chloride ion because of the extremely bulky terpyridyl ligands. The Pd1—N21 bond distance [1.953 (4) Å] with the central pyridine ring is shorter than those with the pyridine rings on either side [2.0913 (4) and 2.089 (4) Å]. The N21—Pd1—Cl1 angle is 161.42 (14)° and the Pd1 ion sits 0.156 Å from the N11—N12—N31 plane. It has been reported that similar 3 N with terpyridine and a chloride coordination gives an almost planer coordination geometry, with similar Pd—N bond distances and a linear N—Pd—Cl angle of 193.6° (Intille et al., 1973). The bulkiness of the dimesityl groups in the 6,6''-positions the of terpyridine ligands distrupts the square-planar coordination towards a tetrahedral geometry, that results in shortning of the Pd—Cl bond length from 2.331 (1) to 2.286 (1) Å. Our ligand design of bulky derivatization in terpyridine ligands successfully induces a distortion in Pd coordination geometry.

Experimental top

A solution of Pd(PPh3)4 (57.5 mg, 0.05 mmol), mesitylboronic acid (935 mg, 5.7 mmol), 6,6''-dibromo-2,2':6',2''-terpyridine (740 mg, 1.9 mmol) and Na3PO4.12H2O (3 g, 7.9 mmol) in a mixture of DME (18 ml) and H2O (3 ml) were refluxed for 20 h under an argon atmosphere. The solution was cooled to room temperature and the solvent evaporated under reduced pressure. The residue was extracted with benzene, washed with brine and dried over MgSO4. Solvents were removed under reduced pressure to give white precipitate, which was collected with filtration and washed with hexane. The precipitate was dried in vacuo and recrystallized from toluene to give microcrystals. Yield 510 mg, 57%. (m.p. 553 K). Spectroscopic analysis: 1H NMR (CDCl3 at 298 K): 2.11 (s, 12H), 2.35 (s, 6H), 6.98 (s, 4H), 7.26 (d, 2H), 7.83 (t, 1H), 7.92 (t, 2H), 8.50 (d, 2H), 8.59 (dd, 2H); analysis calculated for C33H31N3: C 84.40, H 6.65, N 8.95%; found: C 84.04, H 6.55, N 8.92%. A solution of dmtpy (15.0 mg, 0.032 mmol) in CH2Cl2 (1.5 ml) was added to a solution of trans-Pd(MeCN)2Cl2 (8.3 mg, 0.032 mmol) in CH2Cl2(1.0 ml) and stirred at room temperature for 20 h to give a yellow precipitate. The yellow powder was washed with pentane and dried in vacuo. The product was recrystallized from dichloromethane/hexane to give crystals suitable for X-ray analysis. Spectroscpic analysis: 1H NMR (CDCl3 at 298 K) 2.18 (s, 12H), 2.23 (s, 6H), 6.78 (s, 4H), 7.39 (2H, d), 8.31 (2H, t), 8.95 (2H, d), 9.00 (1H, t), 9.21 (2H, d); analysis calculated for C69H68N6Pd3Cl12: C 48.01. H 3.97, N 4.87%; found: C 47.62, H 3.88, N 4.86%.

Refinement top

Data collection and cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); data reduction: TEXSAN (Molecular Structure Corporation, 1999)

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. (a) The molecular structure of (I), with 25% probability displacement ellipsoids. Neighboring atoms in the [PdIICl4]2− anion are shown for clarity. Atoms C2, Cl121 and Cl122 of the chloroform molecule are disordered and only one set is shown for clarity. (b) The cation of (I), showing the labeling of non-H atoms and 25% probability displacement ellipsoids.
[Figure 2] Fig. 2. Space-filling drawing of the cation of (I). Key: red (Pd), green (Cl) and purple (N).
(I) top
Crystal data top
[PdCl(C33H31N3)]2[PdCl4]·4CH2Cl2Z = 1
Mr = 1810.82F(000) = 908
Triclinic, P1Dx = 1.574 Mg m3
a = 10.6555 (7) ÅMo Kα radiation, λ = 0.71069 Å
b = 21.3398 (5) ÅCell parameters from 12443 reflections
c = 8.5995 (1) Åθ = 2.3–27.4°
α = 91.21°µ = 1.23 mm1
β = 100.468 (7)°T = 200 K
γ = 83.566 (7)°Platelet, orange
V = 1910.75 (14) Å30.15 × 0.15 × 0.05 mm
Data collection top
Rigaku R-AXIS-RAPID Imaging Plate
diffractometer
8029 independent reflections
Radiation source: fine-focus sealed tube4933 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 2.1°
ω scansh = 1313
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 2727
Tmin = 0.777, Tmax = 0.940l = 1111
9543 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.078P)2]
where P = (Fo2 + 2Fc2)/3
8029 reflections(Δ/σ)max < 0.001
455 parametersΔρmax = 0.53 e Å3
2 restraintsΔρmin = 1.36 e Å3
Crystal data top
[PdCl(C33H31N3)]2[PdCl4]·4CH2Cl2γ = 83.566 (7)°
Mr = 1810.82V = 1910.75 (14) Å3
Triclinic, P1Z = 1
a = 10.6555 (7) ÅMo Kα radiation
b = 21.3398 (5) ŵ = 1.23 mm1
c = 8.5995 (1) ÅT = 200 K
α = 91.21°0.15 × 0.15 × 0.05 mm
β = 100.468 (7)°
Data collection top
Rigaku R-AXIS-RAPID Imaging Plate
diffractometer
8029 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
4933 reflections with I > 2σ(I)
Tmin = 0.777, Tmax = 0.940Rint = 0.037
9543 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.53 e Å3
8029 reflectionsΔρmin = 1.36 e Å3
455 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Pd10.36247 (4)0.190898 (18)0.51368 (5)0.04205 (13)
Pd21.00000.00001.00000.04568 (16)
Cl10.34252 (12)0.29833 (6)0.49358 (19)0.0549 (4)
Cl20.92476 (15)0.03122 (8)0.7432 (2)0.0689 (4)
Cl30.80997 (13)0.06468 (7)0.99641 (19)0.0596 (4)
Cl110.6628 (3)0.21062 (11)0.8485 (3)0.1074 (7)
Cl120.7226 (3)0.33957 (16)0.8612 (4)0.1533 (12)
Cl210.7376 (14)0.4774 (5)0.6671 (13)0.219 (6)0.632 (11)
Cl220.6860 (13)0.5227 (3)0.3693 (8)0.200 (5)0.632 (11)
Cl310.7697 (14)0.4826 (7)0.616 (3)0.243 (13)0.368 (11)
Cl320.5549 (11)0.5472 (4)0.3748 (13)0.138 (5)0.368 (11)
N110.5380 (4)0.1671 (2)0.4393 (5)0.0459 (10)
N210.4055 (4)0.1057 (2)0.6002 (6)0.0496 (11)
N310.1908 (4)0.1810 (2)0.5907 (5)0.0474 (11)
C10.6037 (7)0.2902 (4)0.8339 (10)0.083 (2)
H320.54970.29820.72830.100*
H330.54830.30010.91400.100*
C20.6980 (19)0.5429 (11)0.5590 (16)0.109 (8)0.632 (11)
H340.61510.56440.57870.205*0.632 (11)
H350.76450.57210.58780.205*0.632 (11)
C30.672 (4)0.547 (2)0.538 (5)0.18 (3)0.368 (11)
H360.62860.56490.62430.117*0.368 (11)
H370.72900.57790.51710.205*0.368 (11)
C120.6019 (5)0.1116 (2)0.5093 (7)0.0474 (13)
C130.7223 (5)0.0877 (3)0.4840 (7)0.0575 (15)
H10.76590.05110.53880.069*
C140.7791 (5)0.1177 (3)0.3773 (7)0.0591 (15)
H20.86170.10200.35740.070*
C150.7125 (5)0.1712 (3)0.3008 (7)0.0554 (14)
H30.74920.19170.22580.068*
C160.5927 (5)0.1954 (3)0.3319 (6)0.0475 (12)
C220.5287 (5)0.0793 (2)0.6075 (6)0.0464 (13)
C230.5722 (6)0.0257 (3)0.7002 (7)0.0583 (15)
H40.65770.00630.70710.069*
C240.4872 (7)0.0012 (3)0.7826 (7)0.0609 (16)
H50.51450.03640.84250.069*
C250.3629 (6)0.0308 (3)0.7789 (7)0.0634 (17)
H60.30600.01420.83640.076*
C260.3246 (5)0.0855 (3)0.6880 (7)0.0513 (14)
C320.2001 (5)0.1259 (3)0.6762 (7)0.0546 (14)
C330.1026 (6)0.1100 (3)0.7469 (7)0.0602 (16)
H70.11220.07160.80420.073*
C340.0102 (6)0.1503 (4)0.7342 (8)0.075 (2)
H80.07690.14150.78740.089*
C350.0229 (6)0.2033 (3)0.6428 (8)0.0659 (17)
H90.10130.23030.62830.080*
C360.0779 (5)0.2186 (3)0.5698 (7)0.0492 (13)
C410.5212 (5)0.2521 (3)0.2444 (7)0.0467 (12)
C420.5641 (5)0.3116 (3)0.2751 (7)0.0548 (14)
C430.4941 (7)0.3631 (3)0.1927 (8)0.0691 (18)
H100.52320.40350.21200.083*
C440.3830 (7)0.3576 (4)0.0830 (9)0.078 (2)
C450.3455 (7)0.2974 (3)0.0517 (8)0.0734 (19)
H110.27060.29270.02460.089*
C460.4126 (5)0.2447 (3)0.1268 (7)0.0546 (14)
C470.6824 (6)0.3210 (3)0.3985 (9)0.0724 (19)
H120.67640.30070.49760.088*
H130.68730.36630.41690.088*
H140.75950.30230.36060.088*
C480.3053 (11)0.4160 (4)0.0022 (12)0.130 (4)
H150.22080.42270.02900.150*
H160.29450.40950.11680.150*
H170.35120.45310.02690.150*
C490.3739 (7)0.1795 (3)0.0795 (8)0.0741 (19)
H180.35110.15940.17040.090*
H190.44580.15370.04490.090*
H200.29980.18340.00720.090*
C510.0520 (5)0.2740 (3)0.4578 (6)0.0486 (13)
C520.0319 (5)0.3350 (3)0.5200 (7)0.0535 (14)
C530.0018 (6)0.3860 (3)0.4141 (8)0.0628 (16)
H210.01590.42750.45390.073*
C540.0149 (6)0.3762 (3)0.2511 (9)0.0698 (18)
C550.0046 (6)0.3160 (3)0.1944 (8)0.0622 (16)
H220.00430.30930.08360.077*
C560.0374 (5)0.2646 (3)0.2964 (7)0.0535 (14)
C570.0494 (8)0.3475 (4)0.6958 (8)0.083 (2)
H230.13530.32940.74680.097*
H240.01550.32810.73990.097*
H250.03990.39310.71470.097*
C580.0559 (9)0.4319 (4)0.1361 (11)0.107 (3)
H260.12960.45800.16600.130*
H270.08000.41590.02840.130*
H280.01560.45740.14040.130*
C590.0539 (6)0.1991 (3)0.2235 (8)0.0697 (18)
H290.00490.19800.12180.085*
H300.03470.16780.29490.085*
H310.14260.18940.20680.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0328 (2)0.0427 (2)0.0498 (2)0.00475 (15)0.00403 (16)0.00628 (18)
Pd20.0391 (3)0.0428 (3)0.0560 (4)0.0018 (2)0.0132 (3)0.0115 (3)
Cl10.0418 (7)0.0444 (7)0.0806 (10)0.0025 (5)0.0168 (7)0.0079 (7)
Cl20.0596 (9)0.0706 (10)0.0667 (10)0.0169 (7)0.0007 (7)0.0032 (8)
Cl30.0456 (7)0.0628 (9)0.0684 (9)0.0104 (6)0.0143 (7)0.0052 (8)
Cl110.1268 (19)0.0978 (15)0.0898 (15)0.0162 (13)0.0173 (13)0.0090 (12)
Cl120.132 (2)0.152 (3)0.178 (3)0.066 (2)0.001 (2)0.004 (2)
Cl210.410 (18)0.079 (4)0.161 (6)0.005 (7)0.048 (8)0.009 (4)
Cl220.333 (15)0.156 (5)0.143 (5)0.057 (7)0.114 (7)0.010 (4)
Cl310.119 (8)0.068 (6)0.54 (4)0.022 (5)0.074 (14)0.034 (12)
Cl320.142 (9)0.112 (6)0.168 (8)0.044 (6)0.033 (6)0.001 (5)
N110.039 (2)0.047 (2)0.049 (3)0.0032 (18)0.0013 (19)0.004 (2)
N210.042 (2)0.048 (2)0.056 (3)0.0093 (19)0.002 (2)0.003 (2)
N310.041 (2)0.046 (2)0.054 (3)0.0105 (19)0.001 (2)0.009 (2)
C10.071 (5)0.090 (5)0.084 (5)0.003 (4)0.010 (4)0.009 (4)
C20.086 (10)0.077 (13)0.18 (2)0.026 (9)0.043 (11)0.014 (13)
C30.22 (5)0.11 (3)0.15 (4)0.11 (3)0.05 (3)0.03 (3)
C120.037 (3)0.046 (3)0.054 (3)0.001 (2)0.003 (2)0.001 (3)
C130.049 (3)0.053 (3)0.063 (4)0.008 (3)0.002 (3)0.008 (3)
C140.040 (3)0.072 (4)0.062 (4)0.006 (3)0.009 (3)0.009 (3)
C150.047 (3)0.067 (4)0.053 (3)0.004 (3)0.012 (3)0.002 (3)
C160.034 (3)0.057 (3)0.049 (3)0.004 (2)0.005 (2)0.003 (3)
C220.050 (3)0.040 (3)0.044 (3)0.001 (2)0.003 (2)0.010 (2)
C230.072 (4)0.044 (3)0.050 (3)0.002 (3)0.006 (3)0.001 (3)
C240.080 (4)0.044 (3)0.053 (4)0.007 (3)0.003 (3)0.002 (3)
C250.074 (4)0.060 (4)0.055 (4)0.025 (3)0.003 (3)0.010 (3)
C260.053 (3)0.046 (3)0.053 (3)0.016 (2)0.000 (3)0.004 (3)
C320.049 (3)0.064 (4)0.050 (3)0.020 (3)0.004 (3)0.014 (3)
C330.051 (4)0.070 (4)0.062 (4)0.020 (3)0.005 (3)0.017 (3)
C340.050 (4)0.106 (5)0.074 (5)0.022 (4)0.011 (3)0.026 (4)
C350.038 (3)0.085 (5)0.076 (4)0.011 (3)0.007 (3)0.016 (4)
C360.032 (3)0.060 (3)0.056 (3)0.009 (2)0.007 (2)0.009 (3)
C410.040 (3)0.050 (3)0.052 (3)0.005 (2)0.014 (2)0.003 (3)
C420.041 (3)0.062 (4)0.063 (4)0.005 (3)0.015 (3)0.010 (3)
C430.071 (4)0.055 (4)0.084 (5)0.010 (3)0.018 (4)0.010 (3)
C440.077 (5)0.074 (5)0.076 (5)0.012 (4)0.007 (4)0.017 (4)
C450.061 (4)0.084 (5)0.066 (4)0.001 (4)0.008 (3)0.008 (4)
C460.044 (3)0.064 (4)0.055 (3)0.005 (3)0.006 (3)0.005 (3)
C470.050 (4)0.074 (4)0.094 (5)0.018 (3)0.011 (3)0.010 (4)
C480.149 (9)0.086 (6)0.128 (8)0.022 (6)0.031 (7)0.029 (6)
C490.063 (4)0.093 (5)0.060 (4)0.016 (4)0.011 (3)0.008 (4)
C510.031 (3)0.064 (3)0.049 (3)0.005 (2)0.003 (2)0.012 (3)
C520.037 (3)0.063 (4)0.058 (3)0.001 (2)0.005 (2)0.003 (3)
C530.057 (4)0.045 (3)0.083 (5)0.002 (3)0.006 (3)0.003 (3)
C540.053 (4)0.081 (5)0.074 (5)0.003 (3)0.008 (3)0.029 (4)
C550.062 (4)0.068 (4)0.055 (4)0.001 (3)0.012 (3)0.006 (3)
C560.037 (3)0.062 (4)0.061 (4)0.003 (2)0.008 (3)0.007 (3)
C570.081 (5)0.091 (5)0.072 (5)0.006 (4)0.007 (4)0.014 (4)
C580.109 (7)0.092 (6)0.111 (7)0.002 (5)0.000 (5)0.046 (5)
C590.061 (4)0.074 (4)0.069 (4)0.001 (3)0.004 (3)0.005 (4)
Geometric parameters (Å, º) top
Pd1—N211.953 (4)C33—C341.386 (9)
Pd1—N312.089 (4)C33—H70.9500
Pd1—N112.091 (4)C34—C351.371 (9)
Pd1—Cl12.2859 (13)C34—H80.9500
Pd2—Cl32.3149 (13)C35—C361.409 (8)
Pd2—Cl3i2.3149 (13)C35—H90.9500
Pd2—Cl2i2.3190 (16)C36—C511.511 (7)
Pd2—Cl22.3190 (16)C41—C421.401 (8)
Cl11—C11.743 (8)C41—C461.413 (8)
Cl12—C11.718 (8)C42—C431.387 (8)
Cl21—Cl310.62 (3)C42—C471.522 (8)
Cl21—C21.665 (16)C43—C441.388 (10)
Cl22—Cl321.445 (11)C43—H100.9500
Cl22—C21.665 (17)C44—C451.394 (10)
Cl22—Cl312.29 (3)C44—C481.537 (10)
Cl31—C31.70 (3)C45—C461.368 (8)
Cl32—C31.70 (3)C45—H110.9500
N11—C161.362 (7)C46—C491.523 (9)
N11—C121.389 (6)C47—H120.9800
N21—C261.355 (7)C47—H130.9800
N21—C221.360 (7)C47—H140.9800
N31—C361.354 (7)C48—H150.9800
N31—C321.385 (7)C48—H160.9800
C1—H320.9900C48—H170.9800
C1—H330.9900C49—H180.9800
C2—H340.9900C49—H190.9800
C2—H350.9900C49—H200.9800
C3—H360.9900C51—C561.381 (8)
C3—H370.9900C51—C521.405 (8)
C12—C131.380 (8)C52—C531.405 (8)
C12—C221.477 (8)C52—C571.512 (9)
C13—C141.390 (9)C53—C541.397 (10)
C13—H10.9500C53—H210.9500
C14—C151.386 (8)C54—C551.372 (9)
C14—H20.9500C54—C581.536 (9)
C15—C161.392 (7)C55—C561.393 (8)
C15—H30.9500C55—H220.9500
C16—C411.494 (7)C56—C591.525 (8)
C22—C231.394 (7)C57—H230.9800
C23—C241.397 (9)C57—H240.9800
C23—H40.9500C57—H250.9800
C24—C251.397 (9)C58—H260.9800
C24—H50.9500C58—H270.9800
C25—C261.399 (8)C58—H280.9800
C25—H60.9500C59—H290.9800
C26—C321.487 (8)C59—H300.9800
C32—C331.372 (8)C59—H310.9800
N21—Pd1—N3181.28 (18)C34—C35—C36121.4 (6)
N21—Pd1—N1180.39 (18)C34—C35—H9119.3
N31—Pd1—N11160.31 (17)C36—C35—H9119.3
N21—Pd1—Cl1161.42 (14)N31—C36—C35120.1 (5)
N31—Pd1—Cl198.89 (12)N31—C36—C51121.5 (5)
N11—Pd1—Cl1100.78 (12)C35—C36—C51118.2 (5)
Cl3—Pd2—Cl3i180.0C42—C41—C46120.3 (5)
Cl3—Pd2—Cl2i90.50 (5)C42—C41—C16120.2 (5)
Cl3i—Pd2—Cl2i89.50 (5)C46—C41—C16119.4 (5)
Cl3—Pd2—Cl289.51 (5)C43—C42—C41118.4 (6)
Cl3i—Pd2—Cl290.50 (5)C43—C42—C47119.7 (6)
Cl2i—Pd2—Cl2180.0C41—C42—C47121.8 (5)
C16—N11—C12117.9 (4)C42—C43—C44122.2 (6)
C16—N11—Pd1130.5 (3)C42—C43—H10118.9
C12—N11—Pd1111.6 (4)C44—C43—H10118.9
C26—N21—C22123.3 (5)C43—C44—C45117.7 (6)
C26—N21—Pd1116.8 (4)C43—C44—C48120.8 (7)
C22—N21—Pd1117.0 (4)C45—C44—C48121.4 (7)
C36—N31—C32118.0 (5)C46—C45—C44122.5 (6)
C36—N31—Pd1130.9 (4)C46—C45—H11118.8
C32—N31—Pd1111.2 (4)C44—C45—H11118.8
Cl12—C1—Cl11113.2 (4)C45—C46—C41118.6 (6)
Cl12—C1—H32108.9C45—C46—C49120.5 (6)
Cl11—C1—H32108.9C41—C46—C49120.8 (5)
Cl12—C1—H33108.9C42—C47—H12109.5
Cl11—C1—H33108.9C42—C47—H13109.5
H32—C1—H33107.8H12—C47—H13109.5
Cl22—C2—Cl21108.1 (15)C42—C47—H14109.5
Cl22—C2—H34110.1H12—C47—H14109.5
Cl21—C2—H34110.1H13—C47—H14109.5
Cl22—C2—H35110.1C44—C48—H15109.5
Cl21—C2—H35110.1C44—C48—H16109.5
H34—C2—H35108.4H15—C48—H16109.5
Cl32—C3—Cl31126 (3)C44—C48—H17109.5
Cl32—C3—H36105.9H15—C48—H17109.5
Cl31—C3—H36105.9H16—C48—H17109.5
Cl32—C3—H37105.9C46—C49—H18109.5
Cl31—C3—H37105.9C46—C49—H19109.5
H36—C3—H37106.2H18—C49—H19109.5
C13—C12—N11122.3 (5)C46—C49—H20109.5
C13—C12—C22123.0 (5)H18—C49—H20109.5
N11—C12—C22114.7 (4)H19—C49—H20109.5
C12—C13—C14119.3 (5)C56—C51—C52120.6 (5)
C12—C13—H1120.4C56—C51—C36120.5 (5)
C14—C13—H1120.4C52—C51—C36118.6 (5)
C15—C14—C13118.4 (5)C51—C52—C53118.4 (5)
C15—C14—H2120.8C51—C52—C57122.2 (6)
C13—C14—H2120.8C53—C52—C57119.4 (6)
C14—C15—C16121.2 (6)C54—C53—C52120.8 (6)
C14—C15—H3119.4C54—C53—H21119.6
C16—C15—H3119.4C52—C53—H21119.6
N11—C16—C15120.7 (5)C55—C54—C53119.3 (6)
N11—C16—C41119.2 (4)C55—C54—C58120.2 (7)
C15—C16—C41120.0 (5)C53—C54—C58120.4 (7)
N21—C22—C23119.1 (6)C54—C55—C56121.2 (6)
N21—C22—C12113.9 (5)C54—C55—H22119.4
C23—C22—C12127.0 (5)C56—C55—H22119.4
C22—C23—C24118.5 (6)C51—C56—C55119.7 (6)
C22—C23—H4120.7C51—C56—C59122.4 (5)
C24—C23—H4120.7C55—C56—C59117.8 (6)
C25—C24—C23121.4 (6)C52—C57—H23109.5
C25—C24—H5119.3C52—C57—H24109.5
C23—C24—H5119.3H23—C57—H24109.5
C24—C25—C26118.1 (6)C52—C57—H25109.5
C24—C25—H6120.9H23—C57—H25109.5
C26—C25—H6120.9H24—C57—H25109.5
N21—C26—C25119.3 (6)C54—C58—H26109.5
N21—C26—C32114.2 (5)C54—C58—H27109.5
C25—C26—C32126.4 (6)H26—C58—H27109.5
C33—C32—N31122.6 (6)C54—C58—H28109.5
C33—C32—C26122.3 (5)H26—C58—H28109.5
N31—C32—C26115.1 (5)H27—C58—H28109.5
C32—C33—C34119.5 (6)C56—C59—H29109.5
C32—C33—H7120.3C56—C59—H30109.5
C34—C33—H7120.3H29—C59—H30109.5
C35—C34—C33118.3 (6)C56—C59—H31109.5
C35—C34—H8120.9H29—C59—H31109.5
C33—C34—H8120.9H30—C59—H31109.5
C2—Cl21—Cl31—C37 (2)Pd1—N21—C26—C3212.7 (6)
C2—Cl21—Cl31—Cl2241.0 (16)C24—C25—C26—N213.9 (8)
Cl32—Cl22—Cl31—Cl2114 (4)C24—C25—C26—C32176.0 (5)
C2—Cl22—Cl31—Cl2164 (3)C36—N31—C32—C333.7 (8)
Cl32—Cl22—Cl31—C340 (3)Pd1—N31—C32—C33176.5 (5)
C2—Cl22—Cl31—C39 (3)C36—N31—C32—C26177.2 (5)
C2—Cl22—Cl32—C31 (3)Pd1—N31—C32—C262.6 (6)
Cl31—Cl22—Cl32—C331 (2)N21—C26—C32—C33174.7 (5)
N21—Pd1—N11—C16166.3 (5)C25—C26—C32—C335.4 (9)
N31—Pd1—N11—C16144.6 (5)N21—C26—C32—N316.2 (7)
Cl1—Pd1—N11—C1632.5 (5)C25—C26—C32—N31173.7 (5)
N21—Pd1—N11—C1210.3 (3)N31—C32—C33—C340.4 (10)
N31—Pd1—N11—C1232.0 (7)C26—C32—C33—C34178.7 (6)
Cl1—Pd1—N11—C12150.8 (3)C32—C33—C34—C353.8 (10)
N31—Pd1—N21—C2611.1 (4)C33—C34—C35—C363.3 (10)
N11—Pd1—N21—C26176.1 (4)C32—N31—C36—C354.1 (8)
Cl1—Pd1—N21—C2680.8 (6)Pd1—N31—C36—C35176.1 (4)
N31—Pd1—N21—C22172.5 (4)C32—N31—C36—C51170.4 (5)
N11—Pd1—N21—C2214.7 (4)Pd1—N31—C36—C519.4 (8)
Cl1—Pd1—N21—C2280.5 (6)C34—C35—C36—N310.8 (10)
N21—Pd1—N31—C36172.6 (5)C34—C35—C36—C51173.9 (6)
N11—Pd1—N31—C36151.0 (5)N11—C16—C41—C42110.5 (6)
Cl1—Pd1—N31—C3626.2 (5)C15—C16—C41—C4271.0 (7)
N21—Pd1—N31—C327.1 (4)N11—C16—C41—C4671.6 (7)
N11—Pd1—N31—C3228.7 (7)C15—C16—C41—C46106.9 (6)
Cl1—Pd1—N31—C32154.1 (3)C46—C41—C42—C432.9 (9)
Cl32—Cl22—C2—Cl21115.1 (11)C16—C41—C42—C43179.2 (5)
Cl31—Cl22—C2—Cl2116.7 (11)C46—C41—C42—C47178.8 (5)
Cl31—Cl21—C2—Cl2251 (4)C16—C41—C42—C470.8 (9)
Cl22—Cl32—C3—Cl3155 (3)C41—C42—C43—C440.7 (10)
Cl21—Cl31—C3—Cl3297 (5)C47—C42—C43—C44177.6 (7)
Cl22—Cl31—C3—Cl3241 (2)C42—C43—C44—C452.8 (11)
C16—N11—C12—C135.7 (8)C42—C43—C44—C48178.0 (8)
Pd1—N11—C12—C13177.2 (4)C43—C44—C45—C461.2 (11)
C16—N11—C12—C22172.1 (4)C48—C44—C45—C46179.6 (8)
Pd1—N11—C12—C225.0 (5)C44—C45—C46—C412.3 (10)
N11—C12—C13—C144.1 (8)C44—C45—C46—C49175.2 (7)
C22—C12—C13—C14173.5 (5)C42—C41—C46—C454.4 (9)
C12—C13—C14—C150.4 (9)C16—C41—C46—C45177.7 (6)
C13—C14—C15—C161.4 (9)C42—C41—C46—C49173.1 (6)
C12—N11—C16—C153.7 (7)C16—C41—C46—C494.8 (8)
Pd1—N11—C16—C15179.8 (4)N31—C36—C51—C5668.9 (7)
C12—N11—C16—C41174.8 (5)C35—C36—C51—C56105.7 (7)
Pd1—N11—C16—C411.7 (7)N31—C36—C51—C52116.6 (6)
C14—C15—C16—N110.3 (9)C35—C36—C51—C5268.8 (7)
C14—C15—C16—C41178.2 (5)C56—C51—C52—C530.7 (8)
C26—N21—C22—C235.1 (7)C36—C51—C52—C53175.2 (5)
Pd1—N21—C22—C23165.2 (4)C56—C51—C52—C57178.8 (6)
C26—N21—C22—C12176.1 (5)C36—C51—C52—C576.7 (8)
Pd1—N21—C22—C1216.1 (6)C51—C52—C53—C540.1 (9)
C13—C12—C22—N21171.3 (5)C57—C52—C53—C54178.1 (6)
N11—C12—C22—N216.5 (6)C52—C53—C54—C550.5 (10)
C13—C12—C22—C237.3 (9)C52—C53—C54—C58178.1 (6)
N11—C12—C22—C23174.9 (5)C53—C54—C55—C560.1 (10)
N21—C22—C23—C240.1 (8)C58—C54—C55—C56177.7 (6)
C12—C22—C23—C24178.7 (5)C52—C51—C56—C551.1 (8)
C22—C23—C24—C252.7 (8)C36—C51—C56—C55175.5 (5)
C23—C24—C25—C260.9 (9)C52—C51—C56—C59178.0 (5)
C22—N21—C26—C257.1 (8)C36—C51—C56—C593.6 (8)
Pd1—N21—C26—C25167.2 (4)C54—C55—C56—C510.7 (9)
C22—N21—C26—C32172.9 (5)C54—C55—C56—C59178.4 (6)
Symmetry code: (i) x+2, y, z+2.

Experimental details

Crystal data
Chemical formula[PdCl(C33H31N3)]2[PdCl4]·4CH2Cl2
Mr1810.82
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)10.6555 (7), 21.3398 (5), 8.5995 (1)
α, β, γ (°)91.21, 100.468 (7), 83.566 (7)
V3)1910.75 (14)
Z1
Radiation typeMo Kα
µ (mm1)1.23
Crystal size (mm)0.15 × 0.15 × 0.05
Data collection
DiffractometerRigaku R-AXIS-RAPID Imaging Plate
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.777, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections
9543, 8029, 4933
Rint0.037
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.144, 1.00
No. of reflections8029
No. of parameters455
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.53, 1.36

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).

Selected geometric parameters (Å, º) top
Pd1—N211.953 (4)Pd1—N112.091 (4)
Pd1—N312.089 (4)Pd1—Cl12.2859 (13)
N21—Pd1—N3181.28 (18)N21—Pd1—Cl1161.42 (14)
N21—Pd1—N1180.39 (18)N31—Pd1—Cl198.89 (12)
N31—Pd1—N11160.31 (17)N11—Pd1—Cl1100.78 (12)
 

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