Bis[(S,S)-1,2-dimethoxy-1,2-bis­(1-methyl-1H-benzimidazol-2-yl)ethane]palladium(II) dichloride

Chiral crystals of the title salt, [Pd(C₂₀H₂₂N₄O₂)₂]Cl₂, contain [Pd(L1)₂]²⁺ cations [L1 is (S,S)-1,2-dimethoxy-1,2-bis­(1-methyl-1H-benzimidazol-2-yl)ethane] separated by disordered Cl^- anions. Two geometrically constraining L1 ligands coordinate each Pd^II ion facially to yield a distorted tetra­gonal N₄(imine)+O₂(meth­oxy) coordination geometry.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.010 Å
Some non-H atoms missing
• Disorder in solvent or counterion
• R factor = 0.051
• wR factor = 0.156
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT051_ALERT_1_B Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .       9.89 Perc.
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         88 PerFit

Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    2
           From the CIF: _chemical_formula_weight           878.15
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   40.00  480.44
           H         1.01   44.00   44.35
           N        14.01    8.00  112.06
           O        16.00    4.00   64.00
           Cl       35.45    1.05   37.23
           Pd      106.42    1.00  106.42
           Calculated formula weight              844.49
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     878.15
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.07
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C36
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      26.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      87.00 A   3  
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C40 H44 Cl2 N8 O4 Pd1
            Atom count from the _atom_site data:  C40 H44 Cl1.05 N8 O4 Pd1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C40 H44 Cl2 N8 O4 Pd
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         80.00     80.00    0.00
           H         88.00     88.00    0.00
           Cl         4.00      2.10    1.90
           N         16.00     16.00    0.00
           O          8.00      8.00    0.00
           Pd         2.00      2.00    0.00
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               7194
           Count of symmetry unique reflns         4395
           Completeness (_total/calc)            163.69%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2799
           Fraction of Friedel pairs measured     0.637
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Our continuing effort to explore the chemistry of bis(imidazole) and bis(benzimidazole) compounds bridged by alkyl or aryl groups has led to their use as geometrically constraining ligands (Knapp et al., 1990; Stibrany, Lobanov et al., 2004). With several first-row transition metal ions, for example, we have found that certain of these ligands yield mononuclear complexes which are remarkably similar in coordination number and in coordination geometry (Stibrany, Lobanov et al., 2004; Stibrany et al., 2004b). Ligands of this type have also been used to prepare several polynuclear complexes with Cu^II, all of which contain planar Cu₂O₂ groups (Isele et al., 2005). Recently, we reported the structure of the chiral facially coordinated tetragonal 4 + 2 Cu^II complex, [Cu(L1)₂]²⁺·2BF₄⁻ bis(acetonitrile) solvate (Stibrany et al., 2004a), where L1 is (S,S)-1,2-bis(1-methylbenzimidazol-2-yl)-1',2'-bis(methoxy)ethane. Here, we report the structure of the title compound, (I), [Pd(L1)₂]²⁺·2Cl⁻, which extends our exploration of these geometrically constraining ligands to metals in the second-row transition series.

Crystals of (I) contain [Pd(L1)₂]²⁺ cations (Fig. 1) separated by disordered Cl⁻ anions. Each cation is coordinated facially by the imine N atoms of the planar benzimidazole fragments and by one of the methoxy O atoms from each of two L1 ligands, to yield a distorted tetragonal N₄+O₂ coordination geometry, in which the N atoms form a nearly square-planar base (Table 1). The axial O atoms are displaced substantially from the axis normal to the PdN₄ plane towards the ligand to which they are attached. These geometric features of the coordination geometry are qualitatively similar to those observed for the [Cu(L1)₂]²⁺ cation (Stibrany et al., 2004a), the major differences being the M—O distances, which are substantially longer in the Pd cation, and several of the N—M—O angles, which indicate a greater deviation from regular tetragonal symmetry for the Pd species (Table 1). Similarities between the two cations extend to their X-SHAPE in profile (Fig. 2a), the V– or butterfly shape of the bound ligands, and the distorted-boat conformation of the seven-membered chelate rings (Stibrany et al., 2004a). Comparable geometric features have also been observed in related bis(benzimidazole)copper(II) complexes (Isele et al., 2002). Ligand L1, with three torsional degrees of freedom, may be characterized by the torsion angles χ₁, χ₂, and χ₃, which are shown in the scheme of L1 and defined in the legend for Table 1. In both the [Cu(L1)₂]²⁺ and [Pd(L1)₂]²⁺ species, the conformations of the individual ligands of a given cation are clearly distinguished by their χ₁ values, one of which is approximately 10° smaller than the other. However, the corresponding torsion angles for the Cu and Pd species differ on average by only about 2.5°, which gives an alternate measure of the degree to which L1 is a geometrically constraining ligand.

Six-coordinate Pd^II species are uncommon and, based on a search of the Cambridge Structural Database (Version 5.25; Allen, 2002), compound (I) contains what is possibly the first structurally characterized example of a Pd^II complex with N₄+O₂ donation. The Pd—O distances of 2.867 (4) and 2.871 (4) Å are long and there is some question regarding the extent to which these interactions are attractive. Thus, in two six-coordinate Pd^II complexes containing axial methoxy groups, linkages of 2.632 (7) and 2.671 (7) Å were considered bonding, while corresponding lengths of 2.887 and 3.025 Å were considered to be non-bonding (Sun et al., 1998). However, with S(thioether) as an axial ligand in a tetragonally distorted Pd^II complex formed with two 10-crown-S3 thioether ligands, the axial S atoms were found to influence the electronic absorption spectrum of the complex, despite the relatively long Pd^II—S(thioether) distance of 3.11 Å (Grant et al., 1991).

Pd^II–N(benzimidazole) linkages are rare. We are aware of only two examples, both in complexes with distorted square-planar coordination geometry. In these species, the Pd^II–N(benzimidazole) distances of 2.151 (4) and 2.117 (4) Å (Figge et al., 2002) are substantially longer than the corresponding linkages in (I), where the Pd—N distances compare favorably with the Pd^II–N(imidazole) distances, which range from 1.982 (4) to 2.029 (4) Å, reported for several square-planar complexes (Dahan, 1976; Liu et al., 2001; Kurdziel & Glowiak, 2002). Lastly, we note that each cation contains three weak C—H···O interactions, two inter-ligand and one intra-ligand, between the methoxy O atoms and the H atoms of the phenyl fragments from three of the four benzimidazole groups (Table 2).

In the crystal structure of (I), the cations form layers parallel to the (100) planes (Fig. 2) and centered about the plane x = 0. The planes of cations present hydrophobic surfaces, consisting largely of atoms from the methyl and phenyl fragments, to the Cl⁻ anions, which lie between them (Fig. 3). The relatively large size of the cations, coupled with their essentially non-polar surfaces, precludes strong Coulombic and/or ion–dipole interactions with the Cl⁻ anions, consistent with the observed disorder of the Cl⁻ layer. Within a given layer, the cations are linked by edge-over-edge π–π interactions along the b cell direction, and by C—H···π interactions along both the b and c cell directions. Packing of the cations may be visualized qualitatively by focusing on the relative orientation of the benzimidazole planes of adjacent cations, which vary from approximately parallel to approximately perpendicular (Fig. 2).

S2. Experimental

Triethylorthoformate (1 ml) was added to a 50 ml Erlenmeyer flask containing a yellow–orange solution of bis(acetonitrile)palladium(II) dichloride (30 mg, 0.12 mmol) and (S,S)-1,2-bis(1-methylbenzimidazol-2-yl)-1',2'-bis(methoxy)ethane (81 mg, 0.23 mmol) in acetonitrile (10 ml). After gentle warming of solution for 5 min, slow evaporation afforded pale-yellow plates of (I) (yield: 71 mg, 67%). IR (KBr pellet, ν, cm⁻¹): 3435 (br), 2942 (w), 1645 (w), 1533 (m), 1477 (m), 1334(m), 1155 (w), 746 (m).

S3. Refinement

Crystals of (I) were prepared using enantiomerically pure L1, and are, therefore, of necessity chiral, excluding the possibility that the space group is P2₁/m. Initial solution of the structure clearly revealed the cation and four potential sites for Cl⁻ anions in the asymmetric unit. This structure was refined to convergence with four partially occupied Cl⁻ sites to yield l.05 Cl⁻ anions per cation. Examination of the structure at this point using PLATON (Spek, 2003) revealed two voids per asymmetric unit, one of 87 ų and one of 66 ų, both located in the space between the cation layers and therefore likely to contain the missing electron density from any remaining Cl⁻ anions. At this point, a modified data set was generated using the SQUEEZE algorithm (Spek, 2003; van der Sluis & Spek, 1990) to subtract the contribution of the electron density in the voids from the structure factors and, using the modified data set, the structure was re-refined to convergence. PLATON estimated a total integrated electron count of 19 for the two voids, which, when added to the 18.9 electrons corresponding to 1.05 Cl⁻ ions on the four disordered sites, accounts well for the electron count of 36 expected for two Cl⁻ ions. H atoms were positioned geometrically and refined using a riding model, with C—H distances in the range 0.93–0.98 Å, and U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for all others.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

	Fig. 1. The structure of a cation in (I), showing 25% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. A view, approximately normal to (100), of a cation layer in (I). H atoms have been omitted for clarity.
	Fig. 3. A view, approximately along the b axis direction, of the structure of (I). H atoms have been omitted for clarity.

Bis[(S,S)-1,2-dimethoxy-1,2-bis(1-methyl-1H-benzimidazol-2- yl)ethane]palladium(II) dichloride

Crystal data

[Pd(C20H22N4O2)2]Cl2	F(000) = 904
Mr = 878.15	Dx = 1.238 Mg m^−3 Dm = 1.25 (1) Mg m^−3 Dm measured by flotation in CCl4–cyclohexane
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1022 reflections
a = 13.0985 (4) Å	θ = 3.7–24.8°
b = 10.7801 (4) Å	µ = 0.55 mm^−1
c = 17.0783 (6) Å	T = 297 K
β = 102.440 (3)°	Cleaved plate, pale yellow
V = 2354.89 (14) Å^3	0.44 × 0.23 × 0.14 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	7194 independent reflections
Radiation source: fine-focus sealed tube	6863 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ϕ and ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS, Blessing 1995)	h = −15→15
Tmin = 0.779, Tmax = 0.926	k = −11→12
16641 measured reflections	l = −20→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.13P)^2 + 1.0352P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
7194 reflections	Δρmax = 0.97 e Å^−3
522 parameters	Δρmin = −0.47 e Å^−3
25 restraints	Absolute structure: Flack (1983), with how many Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (4)

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	Occ. (<1)
Pd	0.99532 (2)	0.50860 (8)	0.742718 (19)	0.03922 (15)
Cl1	0.4542 (3)	0.3524 (4)	0.8538 (2)	0.0531 (9)	0.35
Cl2	0.5462 (6)	0.6933 (8)	0.6604 (5)	0.0751 (18)	0.25
Cl3	0.4576 (6)	0.8501 (9)	0.8073 (5)	0.087 (3)	0.25
Cl4	0.5965 (9)	0.9201 (12)	0.5782 (6)	0.095 (4)	0.20
O1	0.7778 (3)	0.4668 (5)	0.7387 (3)	0.0600 (12)
O2	0.7576 (4)	0.3005 (6)	0.5512 (3)	0.0702 (13)
O3	1.2581 (4)	0.6592 (6)	0.9506 (3)	0.0676 (14)
O4	1.2002 (3)	0.5960 (5)	0.7366 (3)	0.0585 (11)
N11	0.7604 (4)	0.6061 (6)	0.5498 (3)	0.0551 (13)
N13	0.9083 (3)	0.5652 (5)	0.6370 (3)	0.0448 (10)
N21	0.9156 (4)	0.1513 (5)	0.6471 (3)	0.0561 (12)
N23	0.9758 (4)	0.3308 (4)	0.7038 (3)	0.0454 (10)
N31	1.2001 (5)	0.4064 (6)	0.9573 (3)	0.0650 (14)
N33	1.0778 (4)	0.4562 (5)	0.8544 (3)	0.0442 (10)
N41	1.1055 (4)	0.8486 (5)	0.8348 (3)	0.0580 (13)
N43	1.0200 (3)	0.6854 (5)	0.7783 (3)	0.0435 (10)
C1	0.7519 (5)	0.4436 (7)	0.6556 (4)	0.0553 (15)
H1	0.6763	0.4543	0.6371	0.066*
C11	0.8404 (5)	0.6832 (6)	0.5310 (3)	0.0519 (14)
C12	0.8063 (4)	0.5398 (6)	0.6143 (3)	0.0491 (18)
C13	0.9283 (5)	0.6569 (6)	0.5850 (3)	0.0480 (13)
C14	1.0219 (5)	0.7133 (6)	0.5805 (4)	0.0562 (15)
H14	1.0843	0.6936	0.6159	0.067*
C15	1.0175 (6)	0.8010 (7)	0.5200 (4)	0.0615 (16)
H15	1.0790	0.8394	0.5142	0.074*
C16	0.9244 (6)	0.8332 (7)	0.4679 (4)	0.0692 (19)
H16	0.9239	0.8952	0.4299	0.083*
C17	0.8335 (6)	0.7738 (8)	0.4725 (4)	0.0687 (18)
H17	0.7703	0.7932	0.4381	0.082*
C18	0.6504 (6)	0.5980 (9)	0.5021 (5)	0.081 (2)
H18A	0.6482	0.5459	0.4562	0.121*
H18B	0.6259	0.6795	0.4847	0.121*
H18C	0.6064	0.5635	0.5349	0.121*
C1A	0.6915 (7)	0.4597 (13)	0.7771 (6)	0.107 (4)
H1A1	0.6385	0.5176	0.7524	0.160*
H1A2	0.7145	0.4796	0.8329	0.160*
H1A3	0.6632	0.3772	0.7718	0.160*
C2	0.7800 (5)	0.3121 (6)	0.6350 (4)	0.0549 (15)
H2	0.7338	0.2550	0.6557	0.066*
C21	1.0210 (5)	0.1357 (6)	0.6744 (4)	0.0552 (14)
C22	0.8889 (5)	0.2686 (6)	0.6644 (3)	0.0487 (13)
C23	1.0596 (5)	0.2486 (6)	0.7100 (3)	0.0476 (13)
C24	1.1653 (5)	0.2659 (7)	0.7392 (4)	0.0557 (15)
H24	1.1908	0.3403	0.7633	0.067*
C25	1.2333 (6)	0.1686 (7)	0.7315 (4)	0.0667 (17)
H25	1.3051	0.1783	0.7496	0.080*
C26	1.1928 (7)	0.0572 (9)	0.6965 (5)	0.082 (2)
H26	1.2389	−0.0070	0.6929	0.098*
C27	1.0876 (7)	0.0382 (6)	0.6670 (4)	0.070 (2)
H27	1.0622	−0.0365	0.6432	0.084*
C28	0.8479 (6)	0.0542 (8)	0.6057 (5)	0.077 (2)
H28A	0.8361	0.0675	0.5489	0.116*
H28B	0.7823	0.0561	0.6221	0.116*
H28C	0.8806	−0.0250	0.6187	0.116*
C2A	0.6526 (7)	0.2581 (12)	0.5147 (7)	0.111 (4)
H2A1	0.6477	0.1704	0.5230	0.166*
H2A2	0.6381	0.2754	0.4583	0.166*
H2A3	0.6028	0.3006	0.5389	0.166*
C3	1.2483 (5)	0.5817 (7)	0.8819 (4)	0.0570 (15)
H3	1.3168	0.5458	0.8810	0.068*
C31	1.1160 (6)	0.3343 (7)	0.9624 (4)	0.0678 (19)
C32	1.1751 (4)	0.4791 (6)	0.8940 (3)	0.0506 (17)
C33	1.0391 (5)	0.3678 (6)	0.8980 (3)	0.0500 (13)
C34	0.9355 (5)	0.3161 (6)	0.8884 (4)	0.0561 (15)
H34	0.8822	0.3369	0.8450	0.067*
C35	0.9197 (7)	0.2365 (8)	0.9451 (4)	0.071 (2)
H35	0.8530	0.2043	0.9414	0.085*
C36	1.0003 (12)	0.1994 (9)	1.0101 (6)	0.102 (4)
H36	0.9858	0.1413	1.0465	0.122*
C37	1.0967 (9)	0.2462 (9)	1.0205 (5)	0.090 (3)
H37	1.1493	0.2226	1.0637	0.108*
C38	1.3038 (6)	0.4003 (10)	1.0151 (5)	0.085 (2)
H38A	1.3586	0.3952	0.9858	0.128*
H38B	1.3060	0.3284	1.0485	0.128*
H38C	1.3133	0.4735	1.0479	0.128*
C3A	1.3629 (7)	0.7127 (13)	0.9786 (6)	0.100 (3)
H3A1	1.4147	0.6536	0.9712	0.150*
H3A2	1.3730	0.7332	1.0344	0.150*
H3A3	1.3692	0.7864	0.9484	0.150*
C4	1.2142 (5)	0.6643 (7)	0.8080 (4)	0.0571 (15)
H4	1.2691	0.7259	0.8078	0.069*
C41	1.0006 (5)	0.8795 (6)	0.8207 (4)	0.0541 (14)
C42	1.1127 (4)	0.7331 (6)	0.8082 (3)	0.0474 (13)
C43	0.9453 (4)	0.7743 (5)	0.7837 (3)	0.0445 (12)
C44	0.8364 (5)	0.7757 (6)	0.7609 (3)	0.0533 (14)
H44	0.7998	0.7072	0.7364	0.064*
C45	0.7852 (5)	0.8801 (7)	0.7755 (4)	0.0604 (16)
H45	0.7125	0.8819	0.7616	0.073*
C46	0.8398 (6)	0.9857 (7)	0.8113 (5)	0.073 (2)
H46	0.8024	1.0563	0.8190	0.088*
C47	0.9483 (6)	0.9865 (7)	0.8354 (4)	0.069 (2)
H47	0.9842	1.0553	0.8602	0.083*
C48	1.1908 (6)	0.9315 (8)	0.8757 (5)	0.079 (2)
H48A	1.2000	0.9224	0.9327	0.118*
H48B	1.1731	1.0160	0.8610	0.118*
H48C	1.2546	0.9098	0.8599	0.118*
C4A	1.2919 (6)	0.5900 (11)	0.7035 (5)	0.090 (3)
H4A1	1.2964	0.6636	0.6727	0.136*
H4A2	1.2878	0.5185	0.6694	0.136*
H4A3	1.3528	0.5839	0.7461	0.136*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd	0.0373 (2)	0.0393 (2)	0.0410 (2)	−0.00395 (19)	0.00849 (13)	−0.0052 (3)
Cl1	0.0365 (17)	0.063 (3)	0.056 (2)	0.0051 (17)	0.0035 (15)	0.0043 (18)
Cl2	0.075 (4)	0.079 (5)	0.071 (4)	0.010 (4)	0.016 (3)	0.006 (3)
Cl3	0.075 (4)	0.108 (7)	0.080 (5)	−0.055 (5)	0.021 (4)	−0.014 (4)
Cl4	0.088 (6)	0.099 (8)	0.081 (6)	−0.050 (6)	−0.021 (5)	0.016 (6)
O1	0.049 (2)	0.077 (3)	0.060 (2)	−0.008 (2)	0.0238 (18)	−0.0108 (19)
O2	0.053 (2)	0.086 (4)	0.066 (3)	−0.002 (2)	−0.001 (2)	−0.030 (3)
O3	0.060 (3)	0.081 (4)	0.055 (3)	−0.013 (3)	−0.004 (2)	−0.017 (2)
O4	0.042 (2)	0.078 (3)	0.058 (2)	−0.004 (2)	0.0156 (18)	−0.014 (2)
N11	0.047 (3)	0.069 (4)	0.045 (3)	0.005 (3)	−0.001 (2)	−0.003 (2)
N13	0.043 (2)	0.050 (2)	0.041 (2)	−0.005 (2)	0.0071 (18)	−0.0044 (19)
N21	0.069 (3)	0.040 (3)	0.060 (3)	−0.011 (2)	0.014 (2)	−0.010 (2)
N23	0.053 (3)	0.041 (2)	0.043 (2)	−0.008 (2)	0.012 (2)	−0.0065 (19)
N31	0.073 (4)	0.068 (4)	0.048 (3)	0.005 (3)	0.001 (3)	0.002 (3)
N33	0.048 (2)	0.044 (2)	0.041 (2)	0.000 (2)	0.0106 (19)	−0.0052 (18)
N41	0.059 (3)	0.050 (3)	0.061 (3)	−0.009 (3)	0.005 (2)	−0.002 (2)
N43	0.041 (2)	0.043 (3)	0.047 (2)	−0.009 (2)	0.0102 (19)	−0.010 (2)
C1	0.045 (3)	0.064 (4)	0.057 (3)	−0.004 (3)	0.011 (3)	−0.008 (3)
C11	0.058 (3)	0.054 (4)	0.042 (3)	0.007 (3)	0.006 (2)	−0.008 (3)
C12	0.038 (2)	0.056 (5)	0.051 (3)	−0.006 (2)	0.005 (2)	−0.012 (2)
C13	0.054 (3)	0.050 (3)	0.042 (3)	0.001 (3)	0.014 (2)	−0.009 (2)
C14	0.056 (3)	0.058 (4)	0.054 (3)	−0.004 (3)	0.009 (3)	−0.011 (3)
C15	0.068 (4)	0.060 (4)	0.061 (4)	−0.018 (3)	0.024 (3)	−0.007 (3)
C16	0.102 (6)	0.063 (4)	0.047 (3)	0.003 (4)	0.027 (4)	−0.002 (3)
C17	0.078 (5)	0.079 (5)	0.049 (3)	0.005 (4)	0.013 (3)	−0.001 (3)
C18	0.060 (4)	0.096 (6)	0.075 (5)	−0.006 (4)	−0.011 (3)	−0.002 (4)
C1A	0.074 (5)	0.167 (12)	0.092 (6)	0.015 (6)	0.046 (4)	0.015 (6)
C2	0.048 (3)	0.050 (3)	0.067 (4)	−0.019 (3)	0.013 (3)	−0.010 (3)
C21	0.058 (4)	0.054 (4)	0.053 (3)	−0.006 (3)	0.011 (3)	−0.001 (3)
C22	0.054 (3)	0.048 (3)	0.046 (3)	−0.007 (3)	0.015 (2)	−0.002 (2)
C23	0.057 (3)	0.044 (3)	0.042 (3)	0.005 (3)	0.011 (2)	−0.002 (2)
C24	0.057 (3)	0.060 (4)	0.048 (3)	0.005 (3)	0.008 (3)	−0.008 (3)
C25	0.069 (4)	0.061 (4)	0.066 (4)	0.011 (4)	0.005 (3)	−0.002 (3)
C26	0.091 (6)	0.080 (6)	0.074 (5)	0.033 (4)	0.016 (4)	−0.005 (4)
C27	0.099 (5)	0.033 (5)	0.071 (4)	0.010 (3)	0.004 (4)	−0.007 (3)
C28	0.080 (5)	0.058 (4)	0.089 (5)	−0.018 (4)	0.009 (4)	−0.018 (4)
C2A	0.070 (5)	0.124 (9)	0.116 (8)	−0.010 (6)	−0.028 (5)	−0.040 (7)
C3	0.045 (3)	0.072 (4)	0.049 (3)	0.005 (3)	−0.001 (2)	−0.005 (3)
C31	0.096 (5)	0.067 (4)	0.041 (3)	−0.008 (4)	0.016 (3)	−0.006 (3)
C32	0.050 (3)	0.060 (5)	0.041 (2)	0.010 (3)	0.008 (2)	−0.004 (2)
C33	0.065 (3)	0.040 (3)	0.048 (3)	0.001 (3)	0.018 (3)	−0.006 (2)
C34	0.068 (4)	0.054 (4)	0.053 (3)	−0.012 (3)	0.026 (3)	−0.012 (3)
C35	0.099 (6)	0.064 (4)	0.056 (4)	−0.020 (4)	0.030 (4)	−0.011 (4)
C36	0.188 (11)	0.063 (5)	0.071 (5)	−0.039 (7)	0.062 (7)	−0.015 (4)
C37	0.157 (9)	0.066 (5)	0.043 (4)	−0.004 (6)	0.013 (5)	0.011 (4)
C38	0.073 (5)	0.095 (6)	0.076 (5)	0.011 (5)	−0.009 (4)	0.009 (4)
C3A	0.072 (5)	0.124 (9)	0.091 (6)	−0.012 (5)	−0.012 (4)	−0.017 (6)
C4	0.043 (3)	0.071 (4)	0.056 (3)	−0.008 (3)	0.009 (3)	−0.008 (3)
C41	0.064 (4)	0.046 (3)	0.050 (3)	−0.004 (3)	0.007 (3)	0.000 (3)
C42	0.044 (3)	0.048 (3)	0.049 (3)	−0.011 (3)	0.007 (2)	−0.005 (2)
C43	0.054 (3)	0.039 (3)	0.041 (3)	0.002 (2)	0.009 (2)	−0.001 (2)
C44	0.053 (3)	0.056 (4)	0.050 (3)	−0.006 (3)	0.008 (3)	−0.008 (3)
C45	0.050 (3)	0.061 (4)	0.070 (4)	0.008 (3)	0.013 (3)	−0.008 (3)
C46	0.078 (4)	0.051 (5)	0.092 (5)	0.024 (4)	0.021 (4)	−0.004 (4)
C47	0.078 (4)	0.048 (5)	0.078 (4)	−0.002 (3)	0.011 (3)	−0.016 (3)
C48	0.068 (4)	0.067 (5)	0.094 (5)	−0.022 (4)	0.002 (4)	−0.019 (4)
C4A	0.051 (4)	0.146 (9)	0.084 (5)	−0.002 (5)	0.034 (4)	−0.019 (5)

Geometric parameters (Å, º)

Pd—N43	2.006 (5)	C2—H2	0.9800
Pd—N13	2.011 (5)	C21—C27	1.389 (10)
Pd—N23	2.027 (5)	C21—C23	1.405 (9)
Pd—N33	2.058 (5)	C23—C24	1.380 (9)
Pd—O4	2.867 (4)	C24—C25	1.400 (10)
Pd—O1	2.871 (4)	C24—H24	0.9300
O1—C1	1.408 (7)	C25—C26	1.394 (13)
O1—C1A	1.425 (8)	C25—H25	0.9300
O2—C2	1.403 (8)	C26—C27	1.378 (12)
O2—C2A	1.455 (9)	C26—H26	0.9300
O3—C3	1.423 (8)	C27—H27	0.9300
O3—C3A	1.470 (10)	C28—H28A	0.9600
O4—C4	1.402 (8)	C28—H28B	0.9600
O4—C4A	1.436 (7)	C28—H28C	0.9600
N11—C12	1.341 (8)	C2A—H2A1	0.9600
N11—C11	1.428 (9)	C2A—H2A2	0.9600
N11—C18	1.498 (9)	C2A—H2A3	0.9600
N13—C12	1.337 (7)	C3—C32	1.508 (10)
N13—C13	1.391 (8)	C3—C4	1.530 (10)
N21—C22	1.361 (8)	C3—H3	0.9800
N21—C21	1.369 (8)	C31—C33	1.370 (10)
N21—C28	1.454 (9)	C31—C37	1.435 (11)
N23—C22	1.367 (8)	C33—C34	1.443 (9)
N23—C23	1.396 (8)	C34—C35	1.342 (10)
N31—C32	1.318 (8)	C34—H34	0.9300
N31—C31	1.366 (10)	C35—C36	1.415 (16)
N31—C38	1.498 (9)	C35—H35	0.9300
N33—C32	1.331 (7)	C36—C37	1.336 (16)
N33—C33	1.373 (8)	C36—H36	0.9300
N41—C42	1.335 (8)	C37—H37	0.9300
N41—C41	1.384 (9)	C38—H38A	0.9600
N41—C48	1.483 (9)	C38—H38B	0.9600
N43—C42	1.316 (7)	C38—H38C	0.9600
N43—C43	1.386 (7)	C3A—H3A1	0.9600
C1—C12	1.517 (9)	C3A—H3A2	0.9600
C1—C2	1.524 (9)	C3A—H3A3	0.9600
C1—H1	0.9800	C4—C42	1.523 (9)
C11—C13	1.342 (9)	C4—H4	0.9800
C11—C17	1.386 (10)	C41—C47	1.392 (10)
C13—C14	1.385 (9)	C41—C43	1.418 (8)
C14—C15	1.393 (10)	C43—C44	1.396 (8)
C14—H14	0.9300	C44—C45	1.360 (10)
C15—C16	1.389 (11)	C44—H44	0.9300
C15—H15	0.9300	C45—C46	1.411 (11)
C16—C17	1.370 (11)	C45—H45	0.9300
C16—H16	0.9300	C46—C47	1.392 (11)
C17—H17	0.9300	C46—H46	0.9300
C18—H18A	0.9600	C47—H47	0.9300
C18—H18B	0.9600	C48—H48A	0.9600
C18—H18C	0.9600	C48—H48B	0.9600
C1A—H1A1	0.9600	C48—H48C	0.9600
C1A—H1A2	0.9600	C4A—H4A1	0.9600
C1A—H1A3	0.9600	C4A—H4A2	0.9600
C2—C22	1.484 (9)	C4A—H4A3	0.9600
N43—Pd—N13	90.4 (2)	C23—C24—H24	120.9
N43—Pd—N23	177.27 (18)	C25—C24—H24	120.9
N13—Pd—N23	89.2 (2)	C26—C25—C24	119.7 (7)
N43—Pd—N33	87.8 (2)	C26—C25—H25	120.2
N13—Pd—N33	176.39 (18)	C24—C25—H25	120.2
N23—Pd—N33	92.8 (2)	C27—C26—C25	122.9 (7)
N43—Pd—O4	66.92 (15)	C27—C26—H26	118.5
N13—Pd—O4	102.79 (16)	C25—C26—H26	118.5
N23—Pd—O4	110.57 (16)	C26—C27—C21	116.9 (6)
N33—Pd—O4	79.37 (16)	C26—C27—H27	121.6
N43—Pd—O1	104.51 (16)	C21—C27—H27	121.6
N13—Pd—O1	70.04 (16)	N21—C28—H28A	109.5
N23—Pd—O1	77.85 (16)	N21—C28—H28B	109.5
N33—Pd—O1	107.40 (15)	H28A—C28—H28B	109.5
O4—Pd—O1	169.30 (15)	N21—C28—H28C	109.5
C1—O1—C1A	114.3 (6)	H28A—C28—H28C	109.5
C1—O1—Pd	94.2 (3)	H28B—C28—H28C	109.5
C1A—O1—Pd	151.5 (5)	O2—C2A—H2A1	109.5
C2—O2—C2A	115.8 (6)	O2—C2A—H2A2	109.5
C3—O3—C3A	114.3 (6)	H2A1—C2A—H2A2	109.5
C4—O4—C4A	113.7 (5)	O2—C2A—H2A3	109.5
C4—O4—Pd	95.1 (3)	H2A1—C2A—H2A3	109.5
C4A—O4—Pd	150.3 (5)	H2A2—C2A—H2A3	109.5
C12—N11—C11	105.9 (5)	O3—C3—C32	105.3 (5)
C12—N11—C18	128.6 (6)	O3—C3—C4	107.3 (6)
C11—N11—C18	125.3 (6)	C32—C3—C4	117.3 (5)
C12—N13—C13	105.9 (5)	O3—C3—H3	108.9
C12—N13—Pd	122.4 (4)	C32—C3—H3	108.9
C13—N13—Pd	129.8 (4)	C4—C3—H3	108.9
C22—N21—C21	109.1 (5)	N31—C31—C33	105.2 (6)
C22—N21—C28	128.0 (6)	N31—C31—C37	133.2 (8)
C21—N21—C28	122.8 (6)	C33—C31—C37	121.4 (8)
C22—N23—C23	106.5 (5)	N31—C32—N33	110.4 (6)
C22—N23—Pd	131.2 (4)	N31—C32—C3	119.7 (5)
C23—N23—Pd	122.2 (4)	N33—C32—C3	129.3 (5)
C32—N31—C31	109.2 (6)	C31—C33—N33	109.0 (6)
C32—N31—C38	126.6 (7)	C31—C33—C34	120.0 (6)
C31—N31—C38	124.2 (6)	N33—C33—C34	130.9 (6)
C32—N33—C33	106.1 (5)	C35—C34—C33	116.9 (7)
C32—N33—Pd	132.4 (4)	C35—C34—H34	121.5
C33—N33—Pd	120.8 (4)	C33—C34—H34	121.5
C42—N41—C41	107.7 (5)	C34—C35—C36	122.8 (8)
C42—N41—C48	128.4 (6)	C34—C35—H35	118.6
C41—N41—C48	123.8 (6)	C36—C35—H35	118.6
C42—N43—C43	108.0 (5)	C37—C36—C35	121.4 (8)
C42—N43—Pd	124.3 (4)	C37—C36—H36	119.3
C43—N43—Pd	127.4 (4)	C35—C36—H36	119.3
O1—C1—C12	108.2 (5)	C36—C37—C31	117.4 (9)
O1—C1—C2	112.4 (6)	C36—C37—H37	121.3
C12—C1—C2	111.6 (5)	C31—C37—H37	121.3
O1—C1—H1	108.2	N31—C38—H38A	109.5
C12—C1—H1	108.2	N31—C38—H38B	109.5
C2—C1—H1	108.2	H38A—C38—H38B	109.5
C13—C11—C17	123.9 (6)	N31—C38—H38C	109.5
C13—C11—N11	106.5 (5)	H38A—C38—H38C	109.5
C17—C11—N11	129.5 (6)	H38B—C38—H38C	109.5
N13—C12—N11	111.9 (5)	O3—C3A—H3A1	109.5
N13—C12—C1	123.1 (5)	O3—C3A—H3A2	109.5
N11—C12—C1	125.0 (5)	H3A1—C3A—H3A2	109.5
C11—C13—C14	120.5 (6)	O3—C3A—H3A3	109.5
C11—C13—N13	109.7 (5)	H3A1—C3A—H3A3	109.5
C14—C13—N13	129.6 (6)	H3A2—C3A—H3A3	109.5
C13—C14—C15	116.3 (6)	O4—C4—C42	107.9 (5)
C13—C14—H14	121.9	O4—C4—C3	111.8 (6)
C15—C14—H14	121.9	C42—C4—C3	112.4 (5)
C16—C15—C14	122.4 (6)	O4—C4—H4	108.2
C16—C15—H15	118.8	C42—C4—H4	108.2
C14—C15—H15	118.8	C3—C4—H4	108.2
C17—C16—C15	120.0 (7)	N41—C41—C47	132.6 (6)
C17—C16—H16	120.0	N41—C41—C43	106.1 (5)
C15—C16—H16	120.0	C47—C41—C43	121.3 (6)
C16—C17—C11	116.6 (7)	N43—C42—N41	111.7 (5)
C16—C17—H17	121.7	N43—C42—C4	122.8 (5)
C11—C17—H17	121.7	N41—C42—C4	125.4 (5)
N11—C18—H18A	109.5	N43—C43—C44	133.0 (6)
N11—C18—H18B	109.5	N43—C43—C41	106.4 (5)
H18A—C18—H18B	109.5	C44—C43—C41	120.6 (6)
N11—C18—H18C	109.5	C45—C44—C43	118.2 (6)
H18A—C18—H18C	109.5	C45—C44—H44	120.9
H18B—C18—H18C	109.5	C43—C44—H44	120.9
O1—C1A—H1A1	109.5	C44—C45—C46	121.5 (6)
O1—C1A—H1A2	109.5	C44—C45—H45	119.3
H1A1—C1A—H1A2	109.5	C46—C45—H45	119.3
O1—C1A—H1A3	109.5	C47—C46—C45	121.5 (6)
H1A1—C1A—H1A3	109.5	C47—C46—H46	119.2
H1A2—C1A—H1A3	109.5	C45—C46—H46	119.2
O2—C2—C22	106.9 (5)	C41—C47—C46	116.9 (7)
O2—C2—C1	108.2 (6)	C41—C47—H47	121.6
C22—C2—C1	118.6 (5)	C46—C47—H47	121.6
O2—C2—H2	107.6	N41—C48—H48A	109.5
C22—C2—H2	107.6	N41—C48—H48B	109.5
C1—C2—H2	107.6	H48A—C48—H48B	109.5
N21—C21—C27	132.0 (6)	N41—C48—H48C	109.5
N21—C21—C23	106.4 (6)	H48A—C48—H48C	109.5
C27—C21—C23	121.4 (6)	H48B—C48—H48C	109.5
N21—C22—N23	109.7 (5)	O4—C4A—H4A1	109.5
N21—C22—C2	119.6 (6)	O4—C4A—H4A2	109.5
N23—C22—C2	130.5 (6)	H4A1—C4A—H4A2	109.5
C24—C23—N23	130.8 (6)	O4—C4A—H4A3	109.5
C24—C23—C21	120.8 (6)	H4A1—C4A—H4A3	109.5
N23—C23—C21	108.3 (5)	H4A2—C4A—H4A3	109.5
C23—C24—C25	118.3 (6)
N43—Pd—O1—C1	117.4 (4)	C28—N21—C22—N23	−179.8 (6)
N13—Pd—O1—C1	32.3 (4)	C21—N21—C22—C2	175.0 (5)
N23—Pd—O1—C1	−61.2 (4)	C28—N21—C22—C2	−4.1 (10)
N33—Pd—O1—C1	−150.3 (4)	C23—N23—C22—N21	0.8 (6)
O4—Pd—O1—C1	81.6 (7)	Pd—N23—C22—N21	176.9 (4)
N43—Pd—O1—C1A	−62.0 (13)	C23—N23—C22—C2	−174.2 (6)
N13—Pd—O1—C1A	−147.0 (13)	Pd—N23—C22—C2	1.9 (9)
N23—Pd—O1—C1A	119.4 (13)	O2—C2—C22—N21	−58.0 (7)
N33—Pd—O1—C1A	30.3 (13)	C1—C2—C22—N21	179.6 (6)
O4—Pd—O1—C1A	−97.8 (14)	O2—C2—C22—N23	116.6 (7)
N43—Pd—O4—C4	39.2 (4)	C1—C2—C22—N23	−5.8 (9)
N13—Pd—O4—C4	124.1 (4)	C22—N23—C23—C24	175.0 (6)
N23—Pd—O4—C4	−142.0 (4)	Pd—N23—C23—C24	−1.6 (8)
N33—Pd—O4—C4	−53.0 (4)	C22—N23—C23—C21	−0.6 (6)
O1—Pd—O4—C4	77.2 (8)	Pd—N23—C23—C21	−177.2 (4)
N43—Pd—O4—C4A	−154.0 (11)	N21—C21—C23—C24	−175.9 (5)
N13—Pd—O4—C4A	−69.1 (11)	C27—C21—C23—C24	−0.2 (10)
N23—Pd—O4—C4A	24.8 (11)	N21—C21—C23—N23	0.2 (7)
N33—Pd—O4—C4A	113.8 (11)	C27—C21—C23—N23	175.8 (6)
O1—Pd—O4—C4A	−116.0 (12)	N23—C23—C24—C25	−174.3 (6)
N43—Pd—N13—C12	−115.6 (5)	C21—C23—C24—C25	0.7 (9)
N23—Pd—N13—C12	67.1 (5)	C23—C24—C25—C26	−1.3 (10)
O4—Pd—N13—C12	178.0 (4)	C24—C25—C26—C27	1.4 (12)
O1—Pd—N13—C12	−10.3 (4)	C25—C26—C27—C21	−0.9 (12)
N43—Pd—N13—C13	46.7 (5)	N21—C21—C27—C26	174.6 (7)
N23—Pd—N13—C13	−130.6 (5)	C23—C21—C27—C26	0.3 (11)
O4—Pd—N13—C13	−19.6 (5)	C3A—O3—C3—C32	144.0 (7)
O1—Pd—N13—C13	152.1 (5)	C3A—O3—C3—C4	−90.3 (8)
N13—Pd—N23—C22	−44.8 (5)	C32—N31—C31—C33	0.3 (8)
N33—Pd—N23—C22	132.2 (5)	C38—N31—C31—C33	−179.0 (7)
O4—Pd—N23—C22	−148.1 (5)	C32—N31—C31—C37	−175.4 (9)
O1—Pd—N23—C22	25.0 (5)	C38—N31—C31—C37	5.3 (13)
N13—Pd—N23—C23	130.8 (4)	C31—N31—C32—N33	−1.9 (8)
N33—Pd—N23—C23	−52.2 (4)	C38—N31—C32—N33	177.3 (7)
O4—Pd—N23—C23	27.5 (4)	C31—N31—C32—C3	170.5 (6)
O1—Pd—N23—C23	−159.4 (4)	C38—N31—C32—C3	−10.3 (11)
N43—Pd—N33—C32	−59.1 (5)	C33—N33—C32—N31	2.8 (7)
N23—Pd—N33—C32	118.2 (5)	Pd—N33—C32—N31	−167.7 (4)
O4—Pd—N33—C32	7.8 (5)	C33—N33—C32—C3	−168.8 (6)
O1—Pd—N33—C32	−163.7 (5)	Pd—N33—C32—C3	20.8 (9)
N43—Pd—N33—C33	131.5 (4)	O3—C3—C32—N31	−59.8 (8)
N23—Pd—N33—C33	−51.1 (4)	C4—C3—C32—N31	−179.0 (6)
O4—Pd—N33—C33	−161.5 (4)	O3—C3—C32—N33	111.0 (6)
O1—Pd—N33—C33	27.0 (4)	C4—C3—C32—N33	−8.2 (9)
N13—Pd—N43—C42	−129.3 (5)	N31—C31—C33—N33	1.4 (7)
N33—Pd—N43—C42	53.8 (5)	C37—C31—C33—N33	177.7 (7)
O4—Pd—N43—C42	−25.5 (4)	N31—C31—C33—C34	−175.1 (6)
O1—Pd—N43—C42	161.3 (4)	C37—C31—C33—C34	1.3 (11)
N13—Pd—N43—C43	57.6 (5)	C32—N33—C33—C31	−2.6 (7)
N33—Pd—N43—C43	−119.2 (5)	Pd—N33—C33—C31	169.3 (4)
O4—Pd—N43—C43	161.4 (5)	C32—N33—C33—C34	173.4 (6)
O1—Pd—N43—C43	−11.8 (5)	Pd—N33—C33—C34	−14.8 (8)
C1A—O1—C1—C12	135.8 (7)	C31—C33—C34—C35	0.5 (9)
Pd—O1—C1—C12	−43.9 (5)	N33—C33—C34—C35	−175.1 (6)
C1A—O1—C1—C2	−100.6 (8)	C33—C34—C35—C36	−2.5 (11)
Pd—O1—C1—C2	79.7 (4)	C34—C35—C36—C37	2.8 (13)
C12—N11—C11—C13	0.4 (7)	C35—C36—C37—C31	−0.9 (13)
C18—N11—C11—C13	−175.9 (7)	N31—C31—C37—C36	174.1 (8)
C12—N11—C11—C17	−176.2 (6)	C33—C31—C37—C36	−1.0 (13)
C18—N11—C11—C17	7.4 (11)	C4A—O4—C4—C42	143.9 (7)
C13—N13—C12—N11	2.0 (7)	Pd—O4—C4—C42	−43.1 (5)
Pd—N13—C12—N11	168.0 (4)	C4A—O4—C4—C3	−91.9 (8)
C13—N13—C12—C1	179.8 (5)	Pd—O4—C4—C3	81.0 (5)
Pd—N13—C12—C1	−14.3 (8)	O3—C3—C4—O4	−178.8 (5)
C11—N11—C12—N13	−1.5 (7)	C32—C3—C4—O4	−60.7 (7)
C18—N11—C12—N13	174.7 (7)	O3—C3—C4—C42	−57.3 (7)
C11—N11—C12—C1	−179.3 (5)	C32—C3—C4—C42	60.9 (8)
C18—N11—C12—C1	−3.1 (11)	C42—N41—C41—C47	−179.6 (7)
O1—C1—C12—N13	50.4 (7)	C48—N41—C41—C47	2.8 (11)
C2—C1—C12—N13	−73.7 (7)	C42—N41—C41—C43	0.0 (7)
O1—C1—C12—N11	−132.1 (6)	C48—N41—C41—C43	−177.6 (6)
C2—C1—C12—N11	103.8 (7)	C43—N43—C42—N41	1.0 (7)
C17—C11—C13—C14	−6.0 (9)	Pd—N43—C42—N41	−173.3 (4)
N11—C11—C13—C14	177.1 (5)	C43—N43—C42—C4	−176.5 (5)
C17—C11—C13—N13	177.6 (6)	Pd—N43—C42—C4	9.3 (8)
N11—C11—C13—N13	0.8 (6)	C41—N41—C42—N43	−0.6 (7)
C12—N13—C13—C11	−1.7 (6)	C48—N41—C42—N43	176.9 (7)
Pd—N13—C13—C11	−166.2 (4)	C41—N41—C42—C4	176.8 (6)
C12—N13—C13—C14	−177.6 (6)	C48—N41—C42—C4	−5.8 (10)
Pd—N13—C13—C14	17.9 (9)	O4—C4—C42—N43	36.2 (8)
C11—C13—C14—C15	3.0 (9)	C3—C4—C42—N43	−87.6 (7)
N13—C13—C14—C15	178.5 (6)	O4—C4—C42—N41	−140.9 (6)
C13—C14—C15—C16	1.5 (10)	C3—C4—C42—N41	95.3 (8)
C14—C15—C16—C17	−3.2 (11)	C42—N43—C43—C44	179.1 (6)
C15—C16—C17—C11	0.5 (10)	Pd—N43—C43—C44	−6.9 (9)
C13—C11—C17—C16	4.2 (10)	C42—N43—C43—C41	−0.9 (6)
N11—C11—C17—C16	−179.7 (6)	Pd—N43—C43—C41	173.1 (4)
C2A—O2—C2—C22	141.1 (7)	N41—C41—C43—N43	0.6 (6)
C2A—O2—C2—C1	−90.2 (8)	C47—C41—C43—N43	−179.8 (6)
O1—C1—C2—O2	−176.3 (4)	N41—C41—C43—C44	−179.5 (5)
C12—C1—C2—O2	−54.6 (6)	C47—C41—C43—C44	0.1 (9)
O1—C1—C2—C22	−54.5 (7)	N43—C43—C44—C45	179.6 (6)
C12—C1—C2—C22	67.2 (7)	C41—C43—C44—C45	−0.4 (9)
C22—N21—C21—C27	−174.7 (7)	C43—C44—C45—C46	1.2 (10)
C28—N21—C21—C27	4.5 (11)	C44—C45—C46—C47	−1.9 (12)
C22—N21—C21—C23	0.3 (7)	N41—C41—C47—C46	178.8 (7)
C28—N21—C21—C23	179.4 (6)	C43—C41—C47—C46	−0.8 (10)
C21—N21—C22—N23	−0.7 (7)	C45—C46—C47—C41	1.6 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C38—H38C···O3	0.96	2.60	3.012 (12)	106
C34—H34···O1	0.93	2.46	3.342 (9)	158
C14—H14···O4	0.93	2.51	3.387 (8)	157