[N,N′-Bis(diphenyl­phosphino)pyridine-2,6-diamine-κ³P,N¹,P′]chloro­palladium(II) chloride monohydrate 1,2-dichloro­ethane solvate

The title compound, [PdCl(C₂₉H₂₅N₃P₂)]Cl·H₂O·C₂H₄Cl₂, contains a cationic pincer-type PNP complex with Pd in a square-planar coordination. The complexes form dimers which are π–π stacked via their pyridine rings and linked into chains via hydrogen bonds via four-membered rings of two chloride anions and two water mol­ecules. Pairs of 1,2-dichloro­ethane mol­ecules are entrapped in pockets of the structure and show weak inter­actions with palladium.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.035
• wR factor = 0.090
• Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H31C

Author Response: A 1,2-dichloromethane with trans-geometry and enclosed in a pocket is orientation disordered by rotation of about 180deg in Cl(3)---Cl(4) direction, which generates apart from C(30)H~2~ and C(31)H~2~ two extra groups C(30')H~2~ and C(31')H~2~, all with complementary partial occupation. Although PART 1 / PART 2 instructions were used to separate these moieties, program checkCIF PLATON had a problem with this situation for H(31C) and H(31D), but not for H(30C) and H(30D). Program MERCURY (CCDC), on the contrary, has no problems of this sort with the CIF and displays as intended. The mentioned hydrogen atoms are NOT isolated, but bonded to C(31').

PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)        <H31D

Author Response: A 1,2-dichloromethane with trans-geometry and enclosed in a pocket is orientation disordered by rotation of about 180deg in Cl(3)---Cl(4) direction, which generates apart from C(30)H~2~ and C(31)H~2~ two extra groups C(30')H~2~ and C(31')H~2~, all with complementary partial occupation. Although PART 1 / PART 2 instructions were used to separate these moieties, program checkCIF PLATON had a problem with this situation for H(31C) and H(31D), but not for H(30C) and H(30D). Program MERCURY (CCDC), on the contrary, has no problems of this sort with the CIF and displays as intended. The mentioned hydrogen atoms are NOT isolated, but bonded to C(31').

Alert level B
PLAT327_ALERT_2_B Check for Possibly Missing H on sp3? Carbon ....      <C31'

Author Response: This is a consecutive error of PLAT305

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?

Author Response: A problem of checkCIF/PLATON with floating point numbers in chemical formulas, here C31.00 in sum formula.

PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.06
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.97 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C22
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        Cl4
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C31
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.

Author Response: For 1,2-dichloroethane orientation disorder see comment on PLAT305 (vide supra). PLAT241, 242, 243, and 244 are related to this.

PLAT318_ALERT_2_C Check Hybridisation of  N3     in Main Residue .          ?

Author Response: Hybridisation of N3 is sp2 and identical with N2.

PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

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

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT, SADABS (Sheldrick, 1996) and XPREP (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL.

[N,N'-Bis(diphenylphosphino)pyridine-2,6-diamine- κ³P,N¹,P']chloropalladium(II) chloride monohydrate 1,2-dichloroethane solvate

Crystal data

[PdCl(C29H25N3P2)]Cl·H2O·C2H4Cl2	Z = 2
Mr = 771.73	F(000) = 780
Triclinic, P1	Dx = 1.541 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7915 (10) Å	Cell parameters from 7526 reflections
b = 12.2186 (11) Å	θ = 2.5–27.1°
c = 13.5664 (12) Å	µ = 1.01 mm^−1
α = 69.072 (1)°	T = 297 K
β = 89.275 (1)°	Block, yellow
γ = 84.607 (1)°	0.40 × 0.30 × 0.27 mm
V = 1663.0 (3) Å^3

Data collection

Bruker SMART CCD diffractometer	8236 independent reflections
Radiation source: fine-focus sealed tube	6816 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.66, Tmax = 0.76	k = −14→16
22229 measured reflections	l = −18→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.3436P] where P = (Fo^2 + 2Fc^2)/3
8236 reflections	(Δ/σ)max = 0.001
389 parameters	Δρmax = 0.95 e Å^−3
129 restraints	Δρmin = −0.46 e Å^−3

Special details

Experimental. Large yellow prismatic crystals from C₂H₄Cl₂ by slow evaporation in air. The compound is a stable solvate of water and 1,2-dichloroethane.

Bruker Smart APEX CCD three-circle diffractometer. Full sphere data collection with 4 x 300 frames of 0.6deg and 10sec per frame.

Water molecule refined as rigid group (O—H = 0.80 Å, H—O—H = 108°) with no limitations in orientation.

The dichloroethane molecule is orientation disordered for the CH2 groups in 68: 32 proportion, which was taken into account using complementary population parameters, SADI distance restraints and EADP restraints on U^ij (program SHELXL97) in the following fashion: SADI. 0001 Cl3 C30 Cl4 C31 Cl3 C30' Cl4 C31' SADI. 0001 C30 C31 C30' C31' SADI. 02 Cl3 C31 Cl4 C30 Cl3 C31' Cl4 C30' EADP C30 C31 EADP C30' C31'

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	0.729047 (16)	0.596597 (15)	0.272374 (14)	0.03671 (7)
Cl1	0.77641 (7)	0.67467 (7)	0.09702 (5)	0.05991 (19)
Cl2	0.71288 (8)	0.07169 (7)	0.49834 (8)	0.0761 (2)
P1	0.75666 (6)	0.40539 (6)	0.28533 (5)	0.03871 (14)
P2	0.68100 (6)	0.76987 (5)	0.29762 (5)	0.03967 (14)
N1	0.68936 (16)	0.52679 (16)	0.42649 (15)	0.0341 (4)
N2	0.72624 (19)	0.34188 (18)	0.41372 (16)	0.0440 (5)
H2N	0.7322	0.2664	0.4421	0.053*
N3	0.65696 (19)	0.71671 (18)	0.42817 (16)	0.0440 (5)
H3N	0.6446	0.7643	0.4619	0.053*
C1	0.6921 (2)	0.4082 (2)	0.47401 (18)	0.0365 (5)
C2	0.6591 (2)	0.3583 (2)	0.5785 (2)	0.0435 (5)
H2	0.6599	0.2771	0.6110	0.052*
C3	0.6252 (2)	0.4314 (3)	0.6331 (2)	0.0480 (6)
H3	0.6024	0.3989	0.7032	0.058*
C4	0.6243 (2)	0.5515 (2)	0.58637 (19)	0.0443 (5)
H4	0.6025	0.6004	0.6242	0.053*
C5	0.6569 (2)	0.5979 (2)	0.48126 (18)	0.0376 (5)
C6	0.9101 (2)	0.3459 (2)	0.2658 (2)	0.0426 (5)
C7	0.9484 (3)	0.3684 (3)	0.1634 (2)	0.0585 (7)
H7	0.8927	0.4058	0.1070	0.070*
C8	1.0703 (3)	0.3349 (3)	0.1452 (3)	0.0748 (9)
H8	1.0968	0.3501	0.0765	0.090*
C9	1.1510 (3)	0.2799 (3)	0.2279 (4)	0.0791 (10)
H9	1.2331	0.2586	0.2155	0.095*
C10	1.1126 (3)	0.2555 (4)	0.3291 (4)	0.0851 (11)
H10	1.1681	0.2160	0.3852	0.102*
C11	0.9924 (3)	0.2891 (3)	0.3484 (3)	0.0645 (8)
H11	0.9668	0.2733	0.4174	0.077*
C12	0.6504 (2)	0.3562 (2)	0.2121 (2)	0.0447 (5)
C13	0.6691 (3)	0.2460 (3)	0.2065 (3)	0.0619 (8)
H13	0.7394	0.1964	0.2385	0.074*
C14	0.5838 (3)	0.2085 (3)	0.1533 (3)	0.0760 (9)
H14	0.5967	0.1340	0.1492	0.091*
C15	0.4805 (3)	0.2813 (4)	0.1068 (3)	0.0736 (9)
H15	0.4235	0.2558	0.0709	0.088*
C16	0.4597 (3)	0.3904 (3)	0.1122 (3)	0.0702 (8)
H16	0.3884	0.4387	0.0808	0.084*
C17	0.5449 (3)	0.4297 (3)	0.1648 (2)	0.0575 (7)
H17	0.5313	0.5045	0.1683	0.069*
C18	0.7946 (2)	0.8746 (2)	0.2745 (2)	0.0478 (6)
C19	0.8174 (3)	0.9412 (3)	0.1708 (3)	0.0700 (9)
H19	0.7712	0.9353	0.1158	0.084*
C20	0.9106 (4)	1.0173 (3)	0.1500 (4)	0.0936 (12)
H20	0.9266	1.0628	0.0806	0.112*
C21	0.9785 (4)	1.0256 (4)	0.2302 (5)	0.1009 (13)
H21	1.0408	1.0765	0.2151	0.121*
C22	0.9566 (4)	0.9611 (5)	0.3314 (4)	0.1080 (15)
H22	1.0029	0.9679	0.3859	0.130*
C23	0.8631 (3)	0.8834 (4)	0.3538 (3)	0.0815 (10)
H23	0.8482	0.8379	0.4234	0.098*
C24	0.5388 (2)	0.8534 (2)	0.2335 (2)	0.0457 (5)
C25	0.4699 (3)	0.9270 (3)	0.2755 (3)	0.0668 (8)
H25	0.4976	0.9359	0.3366	0.080*
C26	0.3593 (3)	0.9871 (3)	0.2259 (3)	0.0816 (10)
H26	0.3119	1.0349	0.2552	0.098*
C27	0.3195 (3)	0.9777 (4)	0.1369 (3)	0.0838 (11)
H27	0.2468	1.0214	0.1032	0.101*
C28	0.3844 (4)	0.9046 (4)	0.0953 (3)	0.0977 (13)
H28	0.3548	0.8967	0.0343	0.117*
C29	0.4946 (3)	0.8416 (3)	0.1431 (3)	0.0733 (9)
H29	0.5388	0.7914	0.1144	0.088*
O1	0.5779 (2)	0.84294 (18)	0.5562 (2)	0.0686 (6)
H1WA	0.5056	0.8640	0.5434	0.082*
H1WB	0.6137	0.8998	0.5485	0.082*
Cl3	1.01714 (9)	0.59999 (12)	0.37606 (9)	0.1018 (3)
Cl4	1.18668 (16)	0.67626 (15)	0.07676 (11)	0.1374 (5)
C30	1.0746 (5)	0.6836 (4)	0.2495 (3)	0.0730 (11)	0.684 (7)
H30A	1.0102	0.7423	0.2081	0.088*	0.684 (7)
H30B	1.1453	0.7233	0.2577	0.088*	0.684 (7)
C31	1.1117 (5)	0.5995 (4)	0.1972 (3)	0.0730 (11)	0.684 (7)
H31A	1.0391	0.5665	0.1821	0.088*	0.684 (7)
H31B	1.1684	0.5356	0.2428	0.088*	0.684 (7)
C30'	1.0805 (14)	0.5848 (9)	0.2583 (6)	0.099 (3)	0.316 (7)
H30C	1.1563	0.5316	0.2755	0.119*	0.316 (7)
H30D	1.0213	0.5523	0.2257	0.119*	0.316 (7)
C31'	1.1076 (13)	0.7011 (9)	0.1851 (7)	0.099 (3)	0.32
H31C	1.1600	0.7378	0.2194	0.119*	0.316 (7)
H31D	1.0312	0.7520	0.1606	0.119*	0.316 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd	0.03691 (10)	0.03647 (10)	0.03687 (10)	−0.00381 (7)	0.00123 (7)	−0.01318 (7)
Cl1	0.0650 (4)	0.0689 (5)	0.0399 (3)	−0.0002 (4)	0.0049 (3)	−0.0138 (3)
Cl2	0.0777 (5)	0.0482 (4)	0.1039 (7)	−0.0119 (4)	0.0175 (5)	−0.0280 (4)
P1	0.0363 (3)	0.0386 (3)	0.0440 (3)	−0.0029 (2)	−0.0012 (3)	−0.0183 (3)
P2	0.0386 (3)	0.0357 (3)	0.0443 (3)	−0.0040 (2)	0.0012 (3)	−0.0138 (3)
N1	0.0289 (9)	0.0367 (9)	0.0384 (9)	−0.0055 (7)	−0.0001 (7)	−0.0151 (8)
N2	0.0511 (12)	0.0349 (10)	0.0458 (11)	−0.0081 (9)	0.0026 (9)	−0.0134 (9)
N3	0.0511 (12)	0.0378 (10)	0.0462 (11)	−0.0027 (9)	0.0017 (9)	−0.0193 (9)
C1	0.0284 (10)	0.0393 (12)	0.0416 (11)	−0.0068 (9)	−0.0011 (9)	−0.0132 (10)
C2	0.0386 (12)	0.0422 (13)	0.0447 (13)	−0.0096 (10)	0.0013 (10)	−0.0080 (10)
C3	0.0385 (13)	0.0636 (16)	0.0381 (13)	−0.0095 (12)	0.0047 (10)	−0.0124 (11)
C4	0.0420 (13)	0.0531 (14)	0.0400 (12)	−0.0037 (11)	0.0019 (10)	−0.0197 (11)
C5	0.0295 (11)	0.0442 (12)	0.0416 (12)	−0.0055 (9)	−0.0021 (9)	−0.0176 (10)
C6	0.0381 (12)	0.0382 (12)	0.0555 (14)	−0.0064 (10)	0.0015 (10)	−0.0210 (11)
C7	0.0608 (16)	0.0563 (17)	0.0612 (16)	−0.0057 (13)	0.0130 (13)	−0.0247 (14)
C8	0.074 (2)	0.068 (2)	0.088 (2)	−0.0156 (17)	0.0375 (17)	−0.0335 (18)
C9	0.0483 (17)	0.065 (2)	0.127 (3)	−0.0067 (15)	0.0240 (17)	−0.039 (2)
C10	0.0446 (16)	0.099 (3)	0.106 (2)	0.0121 (17)	−0.0118 (18)	−0.035 (2)
C11	0.0469 (15)	0.077 (2)	0.0657 (18)	0.0048 (14)	−0.0045 (13)	−0.0232 (16)
C12	0.0388 (12)	0.0524 (14)	0.0484 (14)	−0.0089 (11)	−0.0008 (10)	−0.0234 (12)
C13	0.0546 (16)	0.0629 (18)	0.080 (2)	−0.0057 (13)	−0.0079 (15)	−0.0397 (17)
C14	0.071 (2)	0.084 (2)	0.096 (3)	−0.0218 (17)	−0.0012 (18)	−0.056 (2)
C15	0.067 (2)	0.101 (2)	0.065 (2)	−0.0343 (18)	−0.0039 (15)	−0.0381 (19)
C16	0.0488 (17)	0.088 (2)	0.0658 (19)	−0.0140 (16)	−0.0151 (14)	−0.0158 (18)
C17	0.0487 (15)	0.0614 (17)	0.0617 (18)	−0.0045 (12)	−0.0065 (13)	−0.0210 (14)
C18	0.0408 (13)	0.0390 (13)	0.0661 (16)	−0.0052 (10)	0.0044 (11)	−0.0216 (12)
C19	0.0616 (19)	0.0536 (18)	0.078 (2)	−0.0126 (14)	0.0012 (16)	−0.0020 (16)
C20	0.069 (2)	0.064 (2)	0.123 (3)	−0.0187 (18)	0.023 (2)	−0.001 (2)
C21	0.068 (2)	0.071 (2)	0.181 (4)	−0.033 (2)	0.031 (3)	−0.060 (3)
C22	0.087 (3)	0.136 (4)	0.143 (3)	−0.058 (3)	0.018 (3)	−0.088 (3)
C23	0.081 (2)	0.101 (3)	0.084 (2)	−0.039 (2)	0.0076 (18)	−0.052 (2)
C24	0.0399 (12)	0.0379 (13)	0.0523 (14)	−0.0033 (10)	0.0026 (10)	−0.0077 (11)
C25	0.0708 (19)	0.0596 (19)	0.0659 (19)	0.0144 (15)	−0.0037 (15)	−0.0224 (15)
C26	0.072 (2)	0.074 (2)	0.082 (2)	0.0288 (18)	0.0035 (18)	−0.0175 (19)
C27	0.0567 (19)	0.091 (3)	0.081 (2)	0.0199 (18)	−0.0106 (17)	−0.010 (2)
C28	0.077 (2)	0.127 (4)	0.087 (3)	0.031 (2)	−0.036 (2)	−0.045 (2)
C29	0.0655 (19)	0.086 (2)	0.072 (2)	0.0179 (17)	−0.0183 (16)	−0.0376 (19)
O1	0.0703 (14)	0.0502 (12)	0.0924 (17)	−0.0018 (10)	0.0096 (14)	−0.0352 (12)
Cl3	0.0681 (6)	0.1301 (10)	0.0964 (7)	−0.0130 (6)	−0.0066 (5)	−0.0263 (7)
Cl4	0.1612 (13)	0.1569 (13)	0.0982 (9)	−0.0543 (11)	0.0168 (9)	−0.0414 (9)
C30	0.065 (2)	0.058 (2)	0.089 (3)	−0.0082 (17)	−0.0206 (19)	−0.0177 (19)
C31	0.065 (2)	0.058 (2)	0.089 (3)	−0.0082 (17)	−0.0206 (19)	−0.0177 (19)
C30'	0.093 (8)	0.100 (8)	0.095 (6)	−0.016 (5)	−0.013 (5)	−0.020 (5)
C31'	0.093 (8)	0.100 (8)	0.095 (6)	−0.016 (5)	−0.013 (5)	−0.020 (5)

Geometric parameters (Å, º)

Pd—N1	2.0135 (19)	C16—C17	1.389 (4)
Pd—P1	2.2705 (7)	C16—H16	0.9300
Pd—P2	2.2750 (7)	C17—H17	0.9300
Pd—Cl1	2.2957 (7)	C18—C23	1.354 (4)
P1—N2	1.677 (2)	C18—C19	1.384 (4)
P1—C6	1.800 (2)	C19—C20	1.392 (5)
P1—C12	1.802 (3)	C19—H19	0.9300
P2—N3	1.681 (2)	C20—C21	1.358 (6)
P2—C18	1.799 (3)	C20—H20	0.9300
P2—C24	1.805 (3)	C21—C22	1.347 (7)
N1—C5	1.351 (3)	C21—H21	0.9300
N1—C1	1.357 (3)	C22—C23	1.407 (5)
N2—C1	1.368 (3)	C22—H22	0.9300
N2—H2N	0.8600	C23—H23	0.9300
N3—C5	1.371 (3)	C24—C29	1.380 (4)
N3—H3N	0.8600	C24—C25	1.384 (4)
C1—C2	1.385 (3)	C25—C26	1.386 (4)
C2—C3	1.373 (4)	C25—H25	0.9300
C2—H2	0.9300	C26—C27	1.333 (5)
C3—C4	1.375 (4)	C26—H26	0.9300
C3—H3	0.9300	C27—C28	1.356 (5)
C4—C5	1.387 (3)	C27—H27	0.9300
C4—H4	0.9300	C28—C29	1.385 (5)
C6—C11	1.370 (4)	C28—H28	0.9300
C6—C7	1.383 (4)	C29—H29	0.9300
C7—C8	1.386 (4)	O1—H1WA	0.8000
C7—H7	0.9300	O1—H1WB	0.8000
C8—C9	1.359 (5)	Cl3—C30	1.793 (3)
C8—H8	0.9300	Cl3—C30'	1.793 (3)
C9—C10	1.364 (6)	Cl4—C31'	1.793 (3)
C9—H9	0.9300	Cl4—C31	1.794 (3)
C10—C11	1.375 (4)	C30—C31	1.468 (6)
C10—H10	0.9300	C30—H30A	0.9700
C11—H11	0.9300	C30—H30B	0.9700
C12—C13	1.371 (4)	C31—H31A	0.9700
C12—C17	1.389 (4)	C31—H31B	0.9700
C13—C14	1.382 (4)	C30'—C31'	1.468 (6)
C13—H13	0.9300	C30'—H30C	0.9700
C14—C15	1.364 (5)	C30'—H30D	0.9700
C14—H14	0.9300	C31'—H31C	0.9700
C15—C16	1.358 (5)	C31'—H31D	0.9700
C15—H15	0.9300
N1—Pd—P1	83.58 (6)	C16—C15—H15	119.5
N1—Pd—P2	83.11 (6)	C14—C15—H15	119.5
P1—Pd—P2	166.39 (2)	C15—C16—C17	119.9 (3)
N1—Pd—Cl1	179.32 (6)	C15—C16—H16	120.0
P1—Pd—Cl1	95.98 (3)	C17—C16—H16	120.0
P2—Pd—Cl1	97.36 (3)	C16—C17—C12	119.4 (3)
N2—P1—C6	106.96 (11)	C16—C17—H17	120.3
N2—P1—C12	107.44 (11)	C12—C17—H17	120.3
C6—P1—C12	106.41 (12)	C23—C18—C19	120.0 (3)
N2—P1—Pd	98.69 (7)	C23—C18—P2	122.3 (3)
C6—P1—Pd	118.30 (8)	C19—C18—P2	117.5 (2)
C12—P1—Pd	117.80 (9)	C18—C19—C20	118.9 (4)
N3—P2—C18	107.32 (12)	C18—C19—H19	120.5
N3—P2—C24	107.67 (11)	C20—C19—H19	120.5
C18—P2—C24	105.88 (12)	C21—C20—C19	120.6 (4)
N3—P2—Pd	98.92 (7)	C21—C20—H20	119.7
C18—P2—Pd	120.44 (9)	C19—C20—H20	119.7
C24—P2—Pd	115.54 (9)	C22—C21—C20	120.8 (4)
C5—N1—C1	120.3 (2)	C22—C21—H21	119.6
C5—N1—Pd	120.11 (15)	C20—C21—H21	119.6
C1—N1—Pd	119.52 (15)	C21—C22—C23	119.4 (4)
C1—N2—P1	121.10 (17)	C21—C22—H22	120.3
C1—N2—H2N	119.5	C23—C22—H22	120.3
P1—N2—H2N	119.5	C18—C23—C22	120.4 (4)
C5—N3—P2	120.41 (17)	C18—C23—H23	119.8
C5—N3—H3N	119.8	C22—C23—H23	119.8
P2—N3—H3N	119.8	C29—C24—C25	118.8 (3)
N1—C1—N2	117.1 (2)	C29—C24—P2	120.2 (2)
N1—C1—C2	120.6 (2)	C25—C24—P2	121.0 (2)
N2—C1—C2	122.3 (2)	C24—C25—C26	119.4 (3)
C3—C2—C1	118.5 (2)	C24—C25—H25	120.3
C3—C2—H2	120.7	C26—C25—H25	120.3
C1—C2—H2	120.7	C27—C26—C25	121.2 (3)
C2—C3—C4	121.3 (2)	C27—C26—H26	119.4
C2—C3—H3	119.3	C25—C26—H26	119.4
C4—C3—H3	119.3	C26—C27—C28	120.3 (3)
C3—C4—C5	118.2 (2)	C26—C27—H27	119.9
C3—C4—H4	120.9	C28—C27—H27	119.9
C5—C4—H4	120.9	C27—C28—C29	120.4 (4)
N1—C5—N3	117.1 (2)	C27—C28—H28	119.8
N1—C5—C4	120.9 (2)	C29—C28—H28	119.8
N3—C5—C4	122.0 (2)	C24—C29—C28	119.8 (3)
C11—C6—C7	119.8 (3)	C24—C29—H29	120.1
C11—C6—P1	121.9 (2)	C28—C29—H29	120.1
C7—C6—P1	118.1 (2)	H1WA—O1—H1WB	108.1
C6—C7—C8	119.6 (3)	C31—C30—Cl3	106.6 (3)
C6—C7—H7	120.2	C31—C30—H30A	110.4
C8—C7—H7	120.2	Cl3—C30—H30A	110.4
C9—C8—C7	119.9 (3)	C31—C30—H30B	110.4
C9—C8—H8	120.1	Cl3—C30—H30B	110.4
C7—C8—H8	120.1	H30A—C30—H30B	108.6
C8—C9—C10	120.6 (3)	C30—C31—Cl4	108.2 (3)
C8—C9—H9	119.7	C30—C31—H31A	110.1
C10—C9—H9	119.7	Cl4—C31—H31A	110.1
C9—C10—C11	120.2 (4)	C30—C31—H31B	110.1
C9—C10—H10	119.9	Cl4—C31—H31B	110.1
C11—C10—H10	119.9	H31A—C31—H31B	108.4
C6—C11—C10	119.9 (3)	C31'—C30'—Cl3	108.8 (4)
C6—C11—H11	120.0	C31'—C30'—H30C	109.9
C10—C11—H11	120.0	Cl3—C30'—H30C	109.9
C13—C12—C17	119.7 (3)	C31'—C30'—H30D	109.9
C13—C12—P1	121.2 (2)	Cl3—C30'—H30D	109.9
C17—C12—P1	119.0 (2)	H30C—C30'—H30D	108.3
C12—C13—C14	120.2 (3)	C30'—C31'—Cl4	106.1 (4)
C12—C13—H13	119.9	C30'—C31'—H31C	110.5
C14—C13—H13	119.9	Cl4—C31'—H31C	110.5
C15—C14—C13	119.8 (3)	C30'—C31'—H31D	110.5
C15—C14—H14	120.1	Cl4—C31'—H31D	110.5
C13—C14—H14	120.1	H31C—C31'—H31D	108.7
C16—C15—C14	121.0 (3)
N1—Pd—P1—N2	−0.63 (9)	C11—C6—C7—C8	−1.1 (4)
P2—Pd—P1—N2	−12.70 (14)	P1—C6—C7—C8	173.1 (2)
Cl1—Pd—P1—N2	178.85 (8)	C6—C7—C8—C9	0.3 (5)
N1—Pd—P1—C6	−115.30 (11)	C7—C8—C9—C10	1.0 (6)
P2—Pd—P1—C6	−127.37 (13)	C8—C9—C10—C11	−1.6 (6)
Cl1—Pd—P1—C6	64.18 (10)	C7—C6—C11—C10	0.5 (5)
N1—Pd—P1—C12	114.40 (11)	P1—C6—C11—C10	−173.5 (3)
P2—Pd—P1—C12	102.34 (14)	C9—C10—C11—C6	0.9 (6)
Cl1—Pd—P1—C12	−66.11 (10)	N2—P1—C12—C13	−77.1 (3)
N1—Pd—P2—N3	3.93 (9)	C6—P1—C12—C13	37.1 (3)
P1—Pd—P2—N3	16.00 (14)	Pd—P1—C12—C13	172.7 (2)
Cl1—Pd—P2—N3	−175.58 (8)	N2—P1—C12—C17	99.8 (2)
N1—Pd—P2—C18	120.14 (13)	C6—P1—C12—C17	−145.9 (2)
P1—Pd—P2—C18	132.22 (14)	Pd—P1—C12—C17	−10.3 (3)
Cl1—Pd—P2—C18	−59.36 (12)	C17—C12—C13—C14	0.5 (5)
N1—Pd—P2—C24	−110.63 (11)	P1—C12—C13—C14	177.5 (3)
P1—Pd—P2—C24	−98.55 (13)	C12—C13—C14—C15	−0.3 (5)
Cl1—Pd—P2—C24	69.87 (10)	C13—C14—C15—C16	−0.2 (6)
P1—Pd—N1—C5	−178.79 (16)	C14—C15—C16—C17	0.6 (5)
P2—Pd—N1—C5	−1.63 (15)	C15—C16—C17—C12	−0.5 (5)
P1—Pd—N1—C1	−0.64 (15)	C13—C12—C17—C16	−0.1 (4)
P2—Pd—N1—C1	176.52 (16)	P1—C12—C17—C16	−177.1 (2)
C6—P1—N2—C1	125.24 (19)	N3—P2—C18—C23	13.0 (3)
C12—P1—N2—C1	−120.84 (19)	C24—P2—C18—C23	127.8 (3)
Pd—P1—N2—C1	2.01 (19)	Pd—P2—C18—C23	−98.8 (3)
C18—P2—N3—C5	−132.70 (19)	N3—P2—C18—C19	−171.8 (2)
C24—P2—N3—C5	113.72 (19)	C24—P2—C18—C19	−57.0 (3)
Pd—P2—N3—C5	−6.81 (19)	Pd—P2—C18—C19	76.3 (2)
C5—N1—C1—N2	−179.77 (19)	C23—C18—C19—C20	−0.5 (5)
Pd—N1—C1—N2	2.1 (3)	P2—C18—C19—C20	−175.7 (3)
C5—N1—C1—C2	1.4 (3)	C18—C19—C20—C21	0.3 (6)
Pd—N1—C1—C2	−176.75 (16)	C19—C20—C21—C22	−0.4 (7)
P1—N2—C1—N1	−2.8 (3)	C20—C21—C22—C23	0.7 (7)
P1—N2—C1—C2	175.98 (18)	C19—C18—C23—C22	0.7 (6)
N1—C1—C2—C3	−0.8 (3)	P2—C18—C23—C22	175.8 (3)
N2—C1—C2—C3	−179.6 (2)	C21—C22—C23—C18	−0.8 (7)
C1—C2—C3—C4	−0.4 (4)	N3—P2—C24—C29	−136.3 (3)
C2—C3—C4—C5	1.0 (4)	C18—P2—C24—C29	109.2 (3)
C1—N1—C5—N3	179.62 (19)	Pd—P2—C24—C29	−26.8 (3)
Pd—N1—C5—N3	−2.2 (3)	N3—P2—C24—C25	41.4 (3)
C1—N1—C5—C4	−0.8 (3)	C18—P2—C24—C25	−73.1 (3)
Pd—N1—C5—C4	177.36 (17)	Pd—P2—C24—C25	150.8 (2)
P2—N3—C5—N1	6.6 (3)	C29—C24—C25—C26	−0.4 (5)
P2—N3—C5—C4	−172.97 (18)	P2—C24—C25—C26	−178.1 (3)
C3—C4—C5—N1	−0.4 (3)	C24—C25—C26—C27	−1.7 (6)
C3—C4—C5—N3	179.2 (2)	C25—C26—C27—C28	2.8 (7)
N2—P1—C6—C11	−17.2 (3)	C26—C27—C28—C29	−1.9 (7)
C12—P1—C6—C11	−131.8 (2)	C25—C24—C29—C28	1.2 (5)
Pd—P1—C6—C11	92.9 (2)	P2—C24—C29—C28	179.0 (3)
N2—P1—C6—C7	168.7 (2)	C27—C28—C29—C24	−0.2 (7)
C12—P1—C6—C7	54.1 (2)	Cl3—C30—C31—Cl4	−173.3 (3)
Pd—P1—C6—C7	−81.2 (2)	Cl3—C30'—C31'—Cl4	173.5 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···Cl2	0.86	2.25	3.101 (2)	169
N3—H3N···O1	0.86	1.95	2.784 (3)	163
O1—H1WA···Cl2^i	0.80	2.42	3.221 (3)	179
O1—H1WB···Cl2^ii	0.80	2.32	3.117 (2)	171

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z.