[1,2-Bis­(di­phenyl­phosphino)­ethane-P,P']dichloropalladium(II) tris­(deutero­chloro­form) solvate

In the title compound, [PdCl₂(C₂₆H₂₄P₂)]·3CDCl₃, the [PdCl₂(dppe)] mol­ecule adopts a distorted square-planar metal coordination and an asymmetrical twist conformation of the five-membered metallocycle. The structure contains infinite channels filled with deutero­chloro­form of crystallization and displays an (a, b/2, c) subcell.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.013 Å
• Disorder in solvent or counterion
• R factor = 0.063
• wR factor = 0.099
• Data-to-parameter ratio = 16.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................      11.00 Perc.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total              12994
         Count of symmetry unique reflns         7314
         Completeness (_total/calc)            177.66%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      5680
         Fraction of Friedel pairs measured     0.777
         Are heavy atom types Z>Si present          yes
          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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

[PdCl₂(dppe)] (I) was first studied crystallographically by Steffen & Palenik (1976) in the form of its 1:1 solvate with CH₂Cl₂ (II). Later, Singh et al. (1995) determined the crystal structure of pure (I). In the course of our studies of organopalladium phosphine complexes we found that re-crystallization of (I) from deuterochloroform gives a stable 1:3 solvate [PdCl₂(dppe)].3 CDCl₃ (III), the structure of which is reported herein.

The asymmetric unit of (III) comprises two [PdCl₂(dppe)] molecules (A and B) and six molecules of deuterochloroform (Fig. 1). The [PdCl₂(dppe)] molecules are related to each other by an approximate translation of b/2. Atoms, related by this pseudo-translation, are given the same numbers with letters A or B added. The Pd atoms deviate from the ideal b/2 translation by 0.54 Å, P by 0.50 and 0.56 Å, Cl by 0.62 and 0.70 Å, and C atoms by 0.09–1.10 Å with the average 0.55 Å (Fig. 2). These deviations are relatively small, compared to the length of the translation (b/2 = 9.2 Å). The [PdCl₂(dppe)] molecule A has three molecules of deuterochloroform attached to it through C—D···Cl—Pd hydrogen bonds. Two of these molecules, A1 and A3 (see Fig. 1), are hydrogen-bonded to the chloride ligand Cl2A, while molecule A2 forms a bifurcated hydrogen bond with both Cl1A and Cl2A. The positions of deuterochloroform molecules B1, B2 and B3 are roughly related respectively to those of A1, A2 and A3. Molecule B2 also forms a bifurcated hydrogen bond, with Cl1B and Cl2B. Molecule B1 is hydrogen-bonded to Cl2B, but unlike A1, molecule B1 is disordered (see below). In molecule B3, the C5B, Cl9B and Cl0B atoms are related by pseudo-translation to the C5A, Cl9A and Cl0A of molecule A3, but Cl11 is not related to Cl10. Thus B3 can be described as a pseudo-equivalent of A3 with the deuterium and Cl11 atoms `swapped'. Consequently, the deuterium atom of B3 does not point towards the [PdCl₂(dppe)] molecule B, but instead forms a weak hydrogen bond with the Cl7A atom of the A2 molecule, related to the original one by the crystallographic translation b.

Thus structure (III) has an (a, b/2, c) subcell, which is manifested in the diffraction pattern: reflections with k indices even, have intensities on average twice as high as those with k odd. The crystal packing can be described as a clathrate (host–guest complex), in which deuterochloroform molecules occupy infinite channels (parallel to the y axis) in the packing of [PdCl₂(dppe)] molecules (Fig. 3).

The molecular structure of [PdCl₂(dppe)] in (III) is similar to those found in structures (I) and (II). The palladium atom has a slightly distorted square-planar coordination. In molecule A, the PdA, P1A, P2A and Cl1A atoms are coplanar, while Cl2A deviates from their mean plane by 0.160 (4) Å. Probably because of this asymmetric distortion, the Pd—P bond lengths differ by 0.018 Å, or 9 s.u. In molecule B, the distortion is of tetrahedral mode: the the PdCl₂ plane is twisted by 6.4 (1)° with respect to the PdP₂ plane, and the Pd—P distances are identical. In any case, the distortion is probably due to steric strain in the chelating ligand, (Steffen & Palenik, 1976). In both [PdCl₂(dppe)] molecules of (III) the 5-membered metallocycle adopts an asymmetric twist conformation: the C1 and C2 atoms are displaced from the PdP₂ plane in opposite directions, by 0.48 (1) and -0.29 (1) Å in molecule A, 0.50 (1) and -0.28 (1) Å in molecule B.

The average Pd—P and Pd—Cl bond distances of 2.242 (7) and 2.364 (3) Å in (III) are essentially the same as in (II), viz. 2.230 (4) and 2.359 (2) Å (Steffen & Palenik, 1976).

S2. Experimental

[Pd₂(dba)₃]·CHCl₃ (0.10 g, 0.11 mmol), where dba is dibenzylideneacetone, and dppe (0.08 g, 0.20 mmol) were dissolved in toluene (50 mol) under nitrogen and stirred for 2 h. ClCO₂Me (0.02 g, 0.23 mmol) was added and the solution (which turned yellow) was stirred briefly. The solvent was removed in vacuo, the residue was identified as (I) and re-crystallized from deuterochloroform by slow evaporation at room temperature.

S3. Refinement

All H atoms were treated as 'riding', with C(sp²)—H and C(sp³)—H bond distances of 0.95 and 0.99 Å, U(iso) equal to 1.3 U(eq) of the carrying carbon atom for the methylene H atoms and 1.2 U(eq) for the deuterium atoms and phenyl H atoms. Molecule B1 shows rotational disorder around the threefold molecular axis. The disorder was approximated by two sets of chlorine positions: Cl3B, Cl4B, Cl5B with occupancies 0.85 and Cl3D, Cl4D, Cl5D with occupancies 0.15, but the high residual electron density (up to 1.36 e Å^-3) may indicate a continuous rotational disorder. All C—Cl bonds in both orienations of molecule B1 were restrained to similar lengths. Anomalous distribution of reflection intensities, due to the sublattice and the disorder of relatively heavy (Cl) atoms, results in high S and/or weighting scheme parameters. The actual weighting scheme was optimized for the data set, excluding non-positive F².

Computing details

Data collection: SMART (Siemens, 1995a); cell refinement: SMART (Siemens, 1995a); data reduction: SAINT (Siemens, 1995a); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SHELXTL (Siemens, 1995b); software used to prepare material for publication: SHELXTL (Siemens, 1995b).

Figures

	Fig. 1. Two independent formula units of [PdCl2(dppe)].3 CDCl3 (III), showing hydrogen bonds. Displacement ellipsoids are drawn at the 50% probability level. Note different orientations of deuterochloroform molecules A3 and B3.
	Fig. 2. Top: asymmetric unit in the crystal of (III) (H atoms omitted); bottom: its convolution by the b/2 pseudo-translation (molecules A in solid, B in dashed lines; minor components of disordered Cl atoms as well as H and D atoms are omitted).
	Fig. 3. Crystal packing of (III), projection onto the (1 0 1) plane.

dichloro{1,2-bis(diphenylphosphino)ethane-P,P'} palladium(II) tris(deuterochloroform) solvate

Crystal data

C26H24Cl2P2Pd·3(CCl3D)	Dx = 1.634 Mg m^−3
Mr = 936.81	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 447 reflections
a = 16.292 (1) Å	θ = 12–23°
b = 18.404 (1) Å	µ = 1.37 mm^−1
c = 25.317 (2) Å	T = 150 K
V = 7591 (1) Å^3	Plate, yellow
Z = 8	0.34 × 0.25 × 0.08 mm
F(000) = 3712

Data collection

SMART 1K CCD area detector diffractometer	12994 independent reflections
Radiation source: fine-focus sealed tube	9802 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
Detector resolution: 8 pixels mm^-1	θmax = 25.0°, θmin = 1.4°
ω scans	h = −18→19
Absorption correction: integration XPREP SHELXTL (Siemens, 1995b)	k = −21→21
Tmin = 0.701, Tmax = 0.920	l = −30→27
41687 measured reflections

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)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + 5.0304P] where P = (Fo^2 + 2Fc^2)/3
S = 1.78	(Δ/σ)max = 0.005
12994 reflections	Δρmax = 1.36 e Å^−3
787 parameters	Δρmin = −0.98 e Å^−3
15 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (3)

Special details

Experimental. The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 5 sets of ω scans; each set at different ϕ and/or 2θ angles and each scan (25 sec exposure) covering 0.3° in ω. Crystal to detector distance 6.0 cm. 7201 unique reflections (for Laue class) and 5793 Friedel equivalents were measured, of which 5564 and 4238 respectively were observed, I>2σ(I).

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
PdA	0.65695 (3)	0.32151 (3)	0.46803 (3)	0.02142 (15)
Cl1A	0.79465 (12)	0.29190 (11)	0.48789 (9)	0.0335 (6)
Cl2A	0.69709 (13)	0.39035 (11)	0.39369 (9)	0.0328 (6)
P1A	0.52264 (13)	0.34504 (10)	0.45532 (9)	0.0228 (6)
P2A	0.61517 (12)	0.25113 (10)	0.53484 (9)	0.0235 (5)
C1A	0.4687 (4)	0.3159 (4)	0.5156 (3)	0.0227 (19)
H1A1	0.4776	0.3516	0.5443	0.030*
H1A2	0.4090	0.3120	0.5088	0.030*
C2A	0.5043 (4)	0.2425 (4)	0.5312 (4)	0.0262 (19)
H2A1	0.4894	0.2056	0.5044	0.034*
H2A2	0.4817	0.2271	0.5657	0.034*
C11A	0.4873 (5)	0.4364 (4)	0.4408 (4)	0.030 (2)
C12A	0.4964 (5)	0.4644 (4)	0.3900 (3)	0.033 (2)
H12A	0.5235	0.4370	0.3634	0.040*
C13A	0.4659 (6)	0.5326 (5)	0.3782 (4)	0.045 (3)
H13A	0.4732	0.5526	0.3439	0.054*
C14A	0.4238 (6)	0.5728 (5)	0.4172 (4)	0.038 (3)
H14A	0.4013	0.6189	0.4087	0.046*
C15A	0.4143 (5)	0.5452 (4)	0.4672 (4)	0.037 (2)
H15A	0.3879	0.5731	0.4938	0.045*
C16A	0.4449 (5)	0.4766 (4)	0.4794 (3)	0.027 (2)
H16A	0.4370	0.4570	0.5137	0.033*
C21A	0.4822 (5)	0.2902 (4)	0.4016 (3)	0.022 (2)
C22A	0.5339 (6)	0.2488 (5)	0.3698 (3)	0.035 (2)
H22A	0.5913	0.2477	0.3765	0.042*
C23A	0.5006 (6)	0.2079 (5)	0.3282 (4)	0.041 (3)
H23A	0.5360	0.1802	0.3062	0.049*
C24A	0.4182 (5)	0.2073 (4)	0.3189 (3)	0.031 (2)
H24A	0.3968	0.1795	0.2904	0.037*
C25A	0.3655 (5)	0.2482 (4)	0.3509 (3)	0.033 (2)
H25A	0.3080	0.2475	0.3447	0.039*
C26A	0.3972 (5)	0.2892 (4)	0.3918 (4)	0.032 (2)
H26A	0.3618	0.3176	0.4133	0.038*
C31A	0.6344 (5)	0.2899 (4)	0.5994 (4)	0.029 (2)
C32A	0.6035 (5)	0.2587 (5)	0.6456 (3)	0.033 (2)
H32A	0.5745	0.2140	0.6437	0.040*
C33A	0.6142 (6)	0.2921 (5)	0.6940 (4)	0.044 (3)
H33A	0.5928	0.2701	0.7250	0.053*
C34A	0.6581 (6)	0.3557 (6)	0.6980 (4)	0.049 (3)
H34A	0.6649	0.3783	0.7314	0.059*
C35A	0.6893 (6)	0.3871 (5)	0.6535 (4)	0.047 (3)
H35A	0.7197	0.4309	0.6564	0.056*
C36A	0.6774 (5)	0.3562 (4)	0.6045 (4)	0.033 (2)
H36A	0.6992	0.3791	0.5740	0.040*
C41A	0.6528 (4)	0.1581 (3)	0.5350 (4)	0.0226 (19)
C42A	0.6333 (5)	0.1149 (4)	0.4910 (4)	0.036 (2)
H42A	0.6018	0.1349	0.4630	0.043*
C43A	0.6606 (6)	0.0438 (5)	0.4882 (4)	0.051 (3)
H43A	0.6448	0.0144	0.4591	0.061*
C44A	0.7098 (5)	0.0160 (4)	0.5280 (5)	0.048 (3)
H44A	0.7298	−0.0324	0.5256	0.058*
C45A	0.7289 (5)	0.0586 (5)	0.5706 (4)	0.044 (3)
H45A	0.7623	0.0387	0.5977	0.053*
C46A	0.7020 (5)	0.1299 (4)	0.5749 (4)	0.033 (2)
H46A	0.7173	0.1588	0.6044	0.040*
C3A	0.6846 (5)	0.4295 (5)	0.2606 (4)	0.037 (2)
D3A	0.7139	0.4086	0.2918	0.045*
Cl3A	0.74571 (18)	0.41476 (15)	0.20356 (10)	0.0609 (8)
Cl4A	0.6702 (2)	0.52241 (14)	0.27094 (12)	0.0742 (9)
Cl5A	0.58954 (17)	0.38406 (16)	0.25316 (11)	0.0638 (8)
C4A	0.7942 (5)	0.2156 (5)	0.3549 (4)	0.041 (3)
D4A	0.7873	0.2574	0.3797	0.050*
Cl6A	0.74442 (15)	0.23637 (14)	0.29592 (10)	0.0516 (7)
Cl7A	0.90162 (15)	0.20215 (15)	0.34373 (10)	0.0543 (8)
Cl8A	0.7538 (2)	0.13782 (16)	0.38463 (13)	0.0818 (10)
C5A	0.9008 (6)	0.4454 (5)	0.3671 (4)	0.045 (3)
D5A	0.8626	0.4216	0.3928	0.054*
Cl9A	1.00396 (15)	0.43416 (14)	0.39120 (10)	0.0525 (7)
Cl0A	0.89163 (19)	0.40210 (18)	0.30703 (12)	0.0803 (10)
Cl10	0.8772 (2)	0.53581 (17)	0.36420 (16)	0.1042 (13)
PdB	0.62381 (3)	0.82362 (3)	0.46665 (3)	0.02195 (15)
Cl1B	0.76307 (12)	0.80989 (11)	0.49112 (9)	0.0363 (6)
Cl2B	0.65480 (14)	0.89745 (11)	0.39273 (8)	0.0318 (5)
P1B	0.48938 (13)	0.83844 (10)	0.45201 (8)	0.0224 (5)
P2B	0.58582 (12)	0.74672 (10)	0.53059 (9)	0.0239 (5)
C1B	0.4341 (5)	0.8039 (4)	0.5102 (3)	0.024 (2)
H1B1	0.4392	0.8386	0.5399	0.032*
H1B2	0.3751	0.7973	0.5021	0.032*
C2B	0.4743 (4)	0.7307 (4)	0.5252 (3)	0.025 (2)
H2B1	0.4627	0.6941	0.4975	0.033*
H2B2	0.4521	0.7127	0.5592	0.033*
C11B	0.4543 (5)	0.9310 (4)	0.4407 (3)	0.024 (2)
C12B	0.4446 (5)	0.9577 (4)	0.3898 (3)	0.029 (2)
H12B	0.4552	0.9269	0.3604	0.035*
C13B	0.4195 (5)	1.0285 (5)	0.3814 (4)	0.034 (2)
H13B	0.4134	1.0467	0.3465	0.041*
C14B	0.4039 (5)	1.0733 (5)	0.4246 (4)	0.035 (2)
H14B	0.3833	1.1210	0.4190	0.042*
C15B	0.4162 (5)	1.0482 (4)	0.4752 (4)	0.033 (2)
H15B	0.4082	1.0797	0.5045	0.039*
C16B	0.4421 (5)	0.9774 (4)	0.4826 (3)	0.032 (2)
H16B	0.4510	0.9601	0.5175	0.038*
C21B	0.4522 (5)	0.7858 (4)	0.3966 (3)	0.021 (2)
C22B	0.5061 (6)	0.7556 (4)	0.3594 (4)	0.036 (2)
H22B	0.5634	0.7643	0.3623	0.044*
C23B	0.4762 (6)	0.7139 (5)	0.3178 (3)	0.038 (2)
H23B	0.5139	0.6926	0.2937	0.045*
C24B	0.3937 (6)	0.7024 (4)	0.3113 (4)	0.039 (2)
H24B	0.3740	0.6757	0.2818	0.047*
C25B	0.3393 (6)	0.7316 (4)	0.3481 (4)	0.035 (2)
H25B	0.2821	0.7226	0.3447	0.042*
C26B	0.3675 (5)	0.7725 (4)	0.3907 (3)	0.033 (2)
H26B	0.3296	0.7920	0.4155	0.039*
C31B	0.5982 (5)	0.7822 (4)	0.5971 (4)	0.028 (2)
C32B	0.5809 (5)	0.7407 (5)	0.6416 (3)	0.031 (2)
H32B	0.5672	0.6909	0.6373	0.038*
C33B	0.5850 (5)	0.7707 (5)	0.6915 (4)	0.039 (2)
H33B	0.5727	0.7416	0.7215	0.046*
C34B	0.6054 (6)	0.8438 (5)	0.6981 (4)	0.050 (3)
H34B	0.6083	0.8650	0.7322	0.060*
C35B	0.6225 (6)	0.8844 (5)	0.6535 (4)	0.049 (3)
H35B	0.6352	0.9345	0.6575	0.059*
C36B	0.6192 (6)	0.8548 (5)	0.6036 (4)	0.044 (3)
H36B	0.6334	0.8835	0.5737	0.052*
C41B	0.6349 (4)	0.6585 (4)	0.5264 (4)	0.025 (2)
C42B	0.6209 (5)	0.6187 (4)	0.4799 (3)	0.031 (2)
H42B	0.5850	0.6377	0.4537	0.037*
C43B	0.6584 (5)	0.5518 (4)	0.4710 (4)	0.041 (2)
H43B	0.6487	0.5253	0.4395	0.049*
C44B	0.7106 (5)	0.5249 (5)	0.5093 (4)	0.039 (2)
H44B	0.7359	0.4790	0.5040	0.047*
C45B	0.7249 (5)	0.5638 (5)	0.5553 (4)	0.037 (2)
H45B	0.7620	0.5446	0.5807	0.044*
C46B	0.6880 (5)	0.6298 (4)	0.5642 (4)	0.028 (2)
H46B	0.6978	0.6554	0.5961	0.034*
C3B	0.6656 (5)	0.9702 (4)	0.2651 (4)	0.065 (3)
D3B	0.6852	0.9434	0.2971	0.078*
Cl3B	0.5802 (2)	1.02738 (19)	0.28171 (15)	0.0795 (12)	0.85
Cl4B	0.7423 (3)	1.0283 (2)	0.2431 (2)	0.1020 (15)	0.85
Cl5B	0.6342 (2)	0.90924 (17)	0.21743 (14)	0.0725 (11)	0.85
Cl3D	0.7387 (17)	0.9343 (18)	0.2193 (11)	0.158 (13)*	0.15
Cl4D	0.7170 (14)	1.0502 (8)	0.2781 (10)	0.079 (7)*	0.15
Cl5D	0.5769 (13)	0.9255 (16)	0.2477 (13)	0.133 (11)*	0.15
C4B	0.7732 (5)	0.7494 (5)	0.3494 (3)	0.039 (2)
D4B	0.7649	0.7903	0.3749	0.047*
Cl6B	0.73056 (19)	0.77430 (19)	0.28889 (11)	0.0869 (11)
Cl7B	0.87893 (15)	0.73303 (14)	0.34332 (10)	0.0475 (7)
Cl8B	0.72474 (18)	0.67132 (16)	0.37448 (16)	0.0984 (12)
C5B	0.9365 (7)	0.9888 (7)	0.3462 (5)	0.081 (4)
D5B	0.9224	1.0414	0.3419	0.097*
Cl9B	1.0258 (2)	0.9822 (3)	0.38697 (16)	0.1185 (14)
Cl0B	0.9561 (3)	0.9523 (4)	0.28601 (16)	0.166 (2)
Cl11	0.85520 (19)	0.94543 (17)	0.37876 (14)	0.0853 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
PdA	0.0153 (3)	0.0239 (3)	0.0250 (4)	0.0000 (3)	0.0000 (3)	−0.0003 (4)
Cl1A	0.0162 (12)	0.0388 (12)	0.0454 (16)	0.0021 (9)	−0.0027 (10)	−0.0004 (10)
Cl2A	0.0333 (14)	0.0343 (12)	0.0309 (14)	−0.0004 (10)	0.0064 (11)	0.0045 (11)
P1A	0.0157 (13)	0.0259 (12)	0.0270 (15)	0.0025 (9)	0.0010 (10)	−0.0014 (10)
P2A	0.0170 (12)	0.0244 (10)	0.0291 (13)	0.0006 (9)	0.0025 (11)	0.0009 (11)
C1A	0.014 (4)	0.030 (4)	0.024 (5)	0.002 (4)	−0.003 (3)	−0.002 (4)
C2A	0.019 (5)	0.029 (4)	0.031 (5)	−0.007 (3)	−0.003 (4)	0.006 (4)
C11A	0.025 (6)	0.027 (5)	0.038 (6)	−0.003 (4)	0.001 (5)	−0.011 (4)
C12A	0.053 (7)	0.025 (5)	0.023 (6)	0.006 (4)	−0.008 (5)	0.003 (4)
C13A	0.057 (7)	0.037 (6)	0.040 (7)	0.006 (5)	−0.010 (5)	0.003 (5)
C14A	0.040 (7)	0.018 (5)	0.057 (7)	0.008 (4)	−0.020 (5)	0.004 (5)
C15A	0.019 (5)	0.030 (5)	0.063 (7)	0.000 (4)	−0.009 (5)	−0.005 (5)
C16A	0.023 (5)	0.031 (5)	0.028 (6)	−0.003 (4)	0.005 (4)	0.003 (4)
C21A	0.023 (5)	0.032 (5)	0.013 (5)	0.001 (4)	−0.002 (4)	0.003 (4)
C22A	0.027 (6)	0.047 (6)	0.032 (6)	0.004 (5)	0.006 (4)	−0.003 (5)
C23A	0.039 (6)	0.051 (6)	0.034 (6)	0.006 (5)	−0.003 (5)	−0.017 (5)
C24A	0.031 (6)	0.037 (5)	0.024 (6)	−0.007 (4)	−0.001 (4)	0.000 (4)
C25A	0.031 (6)	0.036 (5)	0.032 (6)	−0.014 (4)	−0.004 (4)	0.000 (4)
C26A	0.019 (5)	0.040 (5)	0.037 (6)	0.001 (4)	−0.003 (4)	0.002 (4)
C31A	0.024 (6)	0.026 (5)	0.036 (6)	0.014 (4)	−0.002 (4)	−0.005 (4)
C32A	0.031 (6)	0.045 (5)	0.025 (6)	0.001 (4)	−0.005 (4)	−0.001 (5)
C33A	0.037 (6)	0.075 (7)	0.019 (6)	−0.001 (6)	−0.008 (5)	0.013 (5)
C34A	0.050 (7)	0.064 (7)	0.033 (7)	0.002 (6)	−0.009 (6)	−0.014 (5)
C35A	0.049 (7)	0.051 (6)	0.041 (7)	−0.013 (5)	−0.007 (5)	−0.010 (6)
C36A	0.038 (6)	0.026 (5)	0.037 (6)	0.006 (4)	0.004 (5)	0.012 (4)
C41A	0.015 (4)	0.014 (4)	0.039 (6)	0.004 (3)	0.005 (5)	−0.001 (4)
C42A	0.033 (6)	0.036 (5)	0.040 (6)	0.002 (4)	0.011 (4)	0.002 (4)
C43A	0.044 (7)	0.032 (6)	0.078 (9)	−0.007 (5)	0.009 (6)	−0.018 (5)
C44A	0.024 (6)	0.022 (5)	0.099 (9)	0.001 (4)	0.020 (6)	−0.012 (6)
C45A	0.023 (6)	0.036 (6)	0.074 (8)	−0.003 (5)	−0.009 (5)	0.021 (5)
C46A	0.016 (5)	0.025 (5)	0.059 (7)	−0.006 (4)	0.001 (5)	0.006 (4)
C3A	0.026 (6)	0.045 (5)	0.040 (6)	−0.006 (4)	0.007 (4)	0.005 (5)
Cl3A	0.066 (2)	0.081 (2)	0.0365 (16)	0.0040 (16)	0.0094 (14)	0.0071 (15)
Cl4A	0.101 (3)	0.0504 (16)	0.071 (2)	−0.0013 (17)	0.0017 (18)	−0.0047 (15)
Cl5A	0.0573 (19)	0.079 (2)	0.0556 (19)	−0.0134 (16)	−0.0064 (15)	0.0042 (16)
C4A	0.023 (6)	0.060 (6)	0.041 (6)	−0.001 (5)	0.009 (5)	−0.014 (5)
Cl6A	0.0395 (16)	0.0642 (17)	0.0510 (17)	0.0045 (13)	−0.0082 (13)	−0.0128 (14)
Cl7A	0.0289 (15)	0.088 (2)	0.0465 (17)	0.0027 (13)	−0.0035 (12)	−0.0014 (14)
Cl8A	0.077 (2)	0.081 (2)	0.087 (2)	−0.0137 (18)	0.027 (2)	0.0193 (19)
C5A	0.039 (7)	0.051 (6)	0.045 (7)	0.010 (5)	−0.003 (5)	−0.011 (5)
Cl9A	0.0369 (17)	0.0600 (16)	0.0606 (18)	0.0089 (13)	−0.0080 (14)	0.0032 (14)
Cl0A	0.059 (2)	0.121 (3)	0.061 (2)	−0.0155 (19)	0.0016 (17)	−0.0333 (19)
Cl10	0.098 (3)	0.064 (2)	0.151 (4)	0.038 (2)	−0.051 (3)	−0.011 (2)
PdB	0.0162 (4)	0.0235 (3)	0.0262 (4)	−0.0008 (3)	−0.0001 (3)	−0.0004 (4)
Cl1B	0.0139 (12)	0.0396 (13)	0.0556 (15)	−0.0017 (10)	−0.0055 (10)	0.0037 (11)
Cl2B	0.0328 (13)	0.0322 (11)	0.0305 (13)	−0.0018 (10)	0.0093 (11)	0.0025 (10)
P1B	0.0200 (13)	0.0246 (12)	0.0225 (14)	0.0016 (9)	0.0007 (9)	−0.0001 (9)
P2B	0.0175 (12)	0.0262 (11)	0.0280 (13)	−0.0011 (9)	−0.0026 (11)	0.0027 (12)
C1B	0.023 (5)	0.030 (5)	0.020 (5)	−0.005 (4)	0.006 (4)	−0.001 (4)
C2B	0.024 (5)	0.022 (4)	0.031 (6)	−0.004 (3)	−0.001 (4)	0.005 (4)
C11B	0.013 (5)	0.020 (4)	0.037 (6)	−0.001 (4)	0.003 (4)	0.004 (4)
C12B	0.034 (6)	0.026 (5)	0.026 (6)	−0.004 (4)	0.006 (4)	−0.005 (4)
C13B	0.037 (6)	0.035 (5)	0.031 (6)	−0.002 (4)	−0.001 (5)	0.010 (5)
C14B	0.030 (6)	0.027 (5)	0.049 (7)	0.005 (4)	0.007 (5)	−0.004 (5)
C15B	0.038 (6)	0.021 (4)	0.038 (7)	0.000 (4)	0.005 (5)	−0.002 (4)
C16B	0.030 (5)	0.028 (5)	0.037 (6)	0.007 (4)	0.000 (4)	−0.002 (4)
C21B	0.024 (5)	0.021 (4)	0.019 (5)	−0.008 (4)	−0.001 (4)	0.000 (4)
C22B	0.035 (6)	0.035 (5)	0.039 (6)	0.004 (4)	0.005 (5)	−0.003 (5)
C23B	0.043 (7)	0.051 (6)	0.019 (6)	0.005 (5)	0.006 (5)	−0.006 (4)
C24B	0.041 (7)	0.041 (6)	0.035 (6)	0.006 (5)	−0.010 (5)	−0.012 (4)
C25B	0.029 (6)	0.030 (5)	0.047 (7)	0.000 (4)	−0.013 (5)	0.005 (5)
C26B	0.034 (6)	0.030 (5)	0.034 (6)	−0.002 (4)	−0.005 (5)	−0.002 (4)
C31B	0.012 (5)	0.029 (5)	0.042 (6)	0.005 (4)	−0.007 (4)	0.003 (4)
C32B	0.020 (5)	0.041 (5)	0.034 (6)	−0.001 (4)	0.000 (4)	−0.002 (5)
C33B	0.032 (6)	0.051 (6)	0.033 (6)	0.000 (5)	−0.003 (5)	−0.007 (5)
C34B	0.057 (7)	0.058 (7)	0.035 (7)	0.002 (5)	−0.014 (6)	−0.008 (5)
C35B	0.057 (8)	0.042 (6)	0.050 (7)	0.005 (5)	−0.024 (6)	−0.009 (6)
C36B	0.054 (7)	0.042 (6)	0.035 (7)	0.011 (5)	−0.006 (5)	−0.005 (5)
C41B	0.012 (5)	0.029 (5)	0.035 (6)	−0.002 (3)	−0.003 (4)	0.005 (4)
C42B	0.020 (5)	0.040 (5)	0.032 (6)	−0.008 (4)	−0.004 (4)	0.003 (4)
C43B	0.036 (6)	0.025 (5)	0.061 (7)	−0.006 (4)	−0.003 (6)	−0.008 (5)
C44B	0.026 (6)	0.036 (5)	0.056 (7)	0.005 (5)	0.004 (5)	0.005 (5)
C45B	0.021 (6)	0.046 (6)	0.043 (6)	0.001 (5)	−0.006 (5)	0.008 (5)
C46B	0.019 (5)	0.032 (5)	0.034 (6)	−0.007 (4)	0.004 (4)	0.004 (4)
C3B	0.088 (9)	0.076 (8)	0.031 (7)	−0.005 (7)	0.016 (6)	0.009 (6)
Cl3B	0.078 (3)	0.072 (2)	0.089 (3)	0.017 (2)	0.026 (2)	0.006 (2)
Cl4B	0.077 (3)	0.105 (3)	0.124 (4)	−0.032 (3)	0.021 (3)	0.001 (3)
Cl5B	0.077 (3)	0.063 (2)	0.077 (3)	0.012 (2)	−0.027 (2)	−0.0090 (19)
C4B	0.024 (6)	0.057 (6)	0.036 (6)	0.007 (5)	0.002 (4)	−0.010 (5)
Cl6B	0.069 (2)	0.142 (3)	0.050 (2)	0.056 (2)	−0.0174 (16)	−0.0237 (19)
Cl7B	0.0300 (14)	0.0698 (17)	0.0426 (16)	0.0054 (13)	−0.0012 (12)	−0.0038 (13)
Cl8B	0.056 (2)	0.0531 (18)	0.186 (4)	−0.0014 (17)	0.047 (2)	0.007 (2)
C5B	0.063 (9)	0.083 (9)	0.096 (11)	0.001 (7)	0.019 (8)	0.015 (8)
Cl9B	0.047 (2)	0.186 (4)	0.122 (3)	−0.010 (3)	0.006 (2)	−0.024 (3)
Cl0B	0.106 (4)	0.315 (7)	0.079 (3)	0.039 (4)	0.022 (3)	−0.006 (4)
Cl11	0.062 (2)	0.086 (2)	0.108 (3)	−0.0212 (18)	0.026 (2)	−0.010 (2)

Geometric parameters (Å, º)

PdA—P1A	2.254 (2)	PdB—Cl1B	2.365 (2)
PdA—P2A	2.236 (2)	PdB—Cl2B	2.367 (2)
PdA—Cl1A	2.363 (2)	P1B—C1B	1.841 (7)
PdA—Cl2A	2.361 (2)	P1B—C11B	1.820 (8)
P1A—C1A	1.840 (7)	P1B—C21B	1.810 (8)
P1A—C11A	1.815 (8)	P2B—C2B	1.846 (7)
P1A—C21A	1.818 (8)	P2B—C31B	1.818 (9)
P2A—C2A	1.816 (7)	P2B—C41B	1.813 (7)
P2A—C31A	1.811 (9)	C1B—C2B	1.546 (10)
P2A—C41A	1.818 (7)	C11B—C16B	1.375 (10)
C1A—C2A	1.522 (10)	C11B—C12B	1.389 (11)
C11A—C12A	1.393 (11)	C12B—C13B	1.383 (11)
C11A—C16A	1.406 (10)	C13B—C14B	1.392 (11)
C12A—C13A	1.382 (11)	C14B—C15B	1.376 (11)
C13A—C14A	1.411 (12)	C15B—C16B	1.384 (10)
C14A—C15A	1.373 (12)	C21B—C22B	1.403 (11)
C15A—C16A	1.392 (10)	C21B—C26B	1.409 (11)
C21A—C22A	1.393 (11)	C22B—C23B	1.392 (11)
C21A—C26A	1.407 (11)	C23B—C24B	1.370 (11)
C22A—C23A	1.404 (11)	C24B—C25B	1.394 (12)
C23A—C24A	1.363 (11)	C25B—C26B	1.393 (11)
C24A—C25A	1.399 (11)	C31B—C36B	1.388 (11)
C25A—C26A	1.382 (11)	C31B—C32B	1.389 (11)
C31A—C32A	1.397 (11)	C32B—C33B	1.382 (11)
C31A—C36A	1.412 (11)	C33B—C34B	1.395 (12)
C32A—C33A	1.382 (12)	C34B—C35B	1.383 (12)
C33A—C34A	1.375 (12)	C35B—C36B	1.377 (12)
C34A—C35A	1.363 (13)	C41B—C46B	1.394 (11)
C35A—C36A	1.380 (12)	C41B—C42B	1.405 (11)
C41A—C46A	1.390 (11)	C42B—C43B	1.392 (11)
C41A—C42A	1.406 (11)	C43B—C44B	1.381 (12)
C42A—C43A	1.384 (11)	C44B—C45B	1.387 (11)
C43A—C44A	1.386 (13)	C45B—C46B	1.374 (11)
C44A—C45A	1.369 (13)	C3B—Cl5D	1.721 (10)
C45A—C46A	1.388 (11)	C3B—Cl4D	1.725 (10)
C3A—Cl4A	1.746 (9)	C3B—Cl5B	1.726 (7)
C3A—Cl3A	1.774 (9)	C3B—Cl4B	1.737 (7)
C3A—Cl5A	1.770 (9)	C3B—Cl3D	1.789 (10)
C4A—Cl8A	1.746 (9)	C3B—Cl3B	1.793 (7)
C4A—Cl6A	1.741 (10)	C4B—Cl6B	1.744 (9)
C4A—Cl7A	1.790 (9)	C4B—Cl7B	1.755 (9)
C5A—Cl10	1.709 (9)	C4B—Cl8B	1.759 (9)
C5A—Cl0A	1.725 (9)	C5B—Cl0B	1.696 (12)
C5A—Cl9A	1.800 (9)	C5B—Cl11	1.752 (11)
PdB—P1B	2.238 (2)	C5B—Cl9B	1.789 (12)
PdB—P2B	2.238 (2)
P2A—PdA—P1A	85.63 (8)	C21B—P1B—C11B	106.0 (4)
P2A—PdA—Cl2A	176.27 (8)	C21B—P1B—C1B	105.7 (4)
P1A—PdA—Cl2A	92.98 (8)	C11B—P1B—C1B	107.2 (4)
P2A—PdA—Cl1A	89.68 (8)	C21B—P1B—PdB	113.0 (3)
P1A—PdA—Cl1A	175.26 (8)	C11B—P1B—PdB	116.6 (3)
Cl2A—PdA—Cl1A	91.74 (8)	C1B—P1B—PdB	107.7 (3)
C21A—P1A—C11A	104.4 (4)	C41B—P2B—C31B	109.1 (4)
C21A—P1A—C1A	106.6 (4)	C41B—P2B—C2B	106.6 (3)
C11A—P1A—C1A	106.6 (4)	C31B—P2B—C2B	103.6 (4)
C21A—P1A—PdA	110.6 (3)	C41B—P2B—PdB	113.7 (3)
C11A—P1A—PdA	121.0 (3)	C31B—P2B—PdB	114.3 (3)
C1A—P1A—PdA	106.8 (2)	C2B—P2B—PdB	108.7 (3)
C31A—P2A—C2A	104.6 (4)	C2B—C1B—P1B	106.9 (5)
C31A—P2A—C41A	108.1 (4)	C1B—C2B—P2B	107.2 (5)
C2A—P2A—C41A	104.7 (3)	C16B—C11B—C12B	118.8 (7)
C31A—P2A—PdA	113.7 (3)	C16B—C11B—P1B	120.3 (6)
C2A—P2A—PdA	108.4 (3)	C12B—C11B—P1B	120.8 (6)
C41A—P2A—PdA	116.4 (3)	C13B—C12B—C11B	120.6 (8)
C2A—C1A—P1A	107.0 (5)	C12B—C13B—C14B	119.5 (8)
C1A—C2A—P2A	108.3 (5)	C15B—C14B—C13B	120.4 (8)
C12A—C11A—C16A	119.9 (8)	C14B—C15B—C16B	119.2 (8)
C12A—C11A—P1A	119.7 (6)	C11B—C16B—C15B	121.6 (8)
C16A—C11A—P1A	120.2 (7)	C22B—C21B—C26B	118.3 (8)
C13A—C12A—C11A	119.8 (8)	C22B—C21B—P1B	121.5 (6)
C12A—C13A—C14A	120.0 (9)	C26B—C21B—P1B	120.2 (6)
C15A—C14A—C13A	120.4 (8)	C23B—C22B—C21B	120.5 (8)
C14A—C15A—C16A	119.9 (9)	C24B—C23B—C22B	121.2 (8)
C15A—C16A—C11A	120.0 (8)	C23B—C24B—C25B	119.0 (9)
C22A—C21A—C26A	119.2 (8)	C26B—C25B—C24B	121.1 (9)
C22A—C21A—P1A	121.1 (7)	C25B—C26B—C21B	119.9 (8)
C26A—C21A—P1A	119.7 (6)	C36B—C31B—C32B	119.0 (9)
C21A—C22A—C23A	119.5 (8)	C36B—C31B—P2B	118.8 (7)
C24A—C23A—C22A	121.0 (8)	C32B—C31B—P2B	122.0 (6)
C23A—C24A—C25A	120.0 (8)	C33B—C32B—C31B	120.7 (8)
C26A—C25A—C24A	119.9 (8)	C32B—C33B—C34B	120.4 (10)
C25A—C26A—C21A	120.4 (8)	C35B—C34B—C33B	118.2 (9)
C32A—C31A—C36A	117.2 (8)	C36B—C35B—C34B	121.8 (9)
C32A—C31A—P2A	122.1 (7)	C35B—C36B—C31B	119.9 (10)
C36A—C31A—P2A	120.6 (7)	C46B—C41B—C42B	118.6 (7)
C33A—C32A—C31A	120.9 (9)	C46B—C41B—P2B	124.9 (7)
C34A—C33A—C32A	120.7 (9)	C42B—C41B—P2B	116.4 (6)
C35A—C34A—C33A	119.6 (10)	C43B—C42B—C41B	121.6 (8)
C34A—C35A—C36A	121.1 (9)	C44B—C43B—C42B	118.3 (9)
C35A—C36A—C31A	120.5 (9)	C43B—C44B—C45B	120.5 (9)
C46A—C41A—C42A	119.6 (7)	C46B—C45B—C44B	121.3 (9)
C46A—C41A—P2A	123.2 (7)	C45B—C46B—C41B	119.6 (8)
C42A—C41A—P2A	117.1 (6)	Cl5D—C3B—Cl4D	149.8 (15)
C43A—C42A—C41A	120.3 (9)	Cl5D—C3B—Cl5B	42.3 (11)
C44A—C43A—C42A	119.8 (9)	Cl4D—C3B—Cl5B	146.3 (10)
C45A—C44A—C43A	119.6 (8)	Cl5D—C3B—Cl4B	144.7 (13)
C44A—C45A—C46A	122.1 (9)	Cl4D—C3B—Cl4B	35.6 (8)
C41A—C46A—C45A	118.5 (9)	Cl5B—C3B—Cl4B	112.9 (5)
Cl4A—C3A—Cl3A	110.3 (5)	Cl5D—C3B—Cl3D	102.5 (17)
Cl4A—C3A—Cl5A	111.2 (5)	Cl4D—C3B—Cl3D	96.6 (14)
Cl3A—C3A—Cl5A	109.4 (5)	Cl5B—C3B—Cl3D	60.2 (12)
Cl8A—C4A—Cl6A	112.0 (5)	Cl4B—C3B—Cl3D	62.6 (11)
Cl8A—C4A—Cl7A	108.9 (5)	Cl5D—C3B—Cl3B	71.9 (12)
Cl6A—C4A—Cl7A	110.5 (5)	Cl4D—C3B—Cl3B	80.3 (9)
Cl10—C5A—Cl0A	113.1 (6)	Cl5B—C3B—Cl3B	108.4 (5)
Cl10—C5A—Cl9A	109.7 (5)	Cl4B—C3B—Cl3B	105.8 (5)
Cl0A—C5A—Cl9A	109.0 (5)	Cl3D—C3B—Cl3B	152.2 (13)
P2B—PdB—P1B	85.77 (8)	Cl6B—C4B—Cl7B	111.0 (5)
P2B—PdB—Cl1B	90.47 (8)	Cl6B—C4B—Cl8B	110.6 (5)
P1B—PdB—Cl1B	174.30 (8)	Cl7B—C4B—Cl8B	109.4 (5)
P2B—PdB—Cl2B	173.73 (8)	Cl0B—C5B—Cl11	112.6 (7)
P1B—PdB—Cl2B	90.45 (8)	Cl0B—C5B—Cl9B	109.7 (7)
Cl1B—PdB—Cl2B	93.66 (8)	Cl11—C5B—Cl9B	108.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—D3A···Cl2A	1.00	2.62	3.452 (9)	141
C4A—D4A···Cl1A	1.00	2.81	3.649 (10)	141
C4A—D4A···Cl2A	1.00	2.88	3.717 (9)	142
C5A—D5A···Cl2A	1.00	2.76	3.534 (10)	135
C3B—D3B···Cl2B	1.00	2.61	3.501 (10)	148
C4B—D4B···Cl1B	1.00	2.96	3.759 (9)	137
C4B—D4B···Cl2B	1.00	2.70	3.513 (9)	138
C5B—D5B···Cl7A^i	1.00	2.98	3.967 (13)	170

Symmetry code: (i) x, y+1, z.