Crystal structure of [N,N'-bis­(4-methyl­phen­yl)-1,2-di­phenyl­ethane-1,2-di­imine-[kappa]²N,N']di­chlorido­palladium(II) methanol monosolvate

The title compound, [PdCl₂(C₂₈H₂₄N₂)]·CH₃OH, was pre­pared from the reaction of PdCl₂(DMSO)₂ (DMSO is di­methyl sulfoxide) and N,N'-bis­(4-methyl­phen­yl)-1,2-di­phenyl­ethane-1,2-di­imine in methanol. The chelating di­imine core of the title compound deviates slightly from planarity, with an N-C-C-N torsion angle of 5.3 (3)°. Delocalization in the di­imine core is indicated by N-C and C-C bonds that are, respectively, longer and shorter than those found in related nonchelating di­imines. The distorted square-planar coordination environment around the Pd^II atom is manifested as bond angles that are smaller and larger than 90°, and palladacycle torsion angles of -173.22 (16) and 167.06 (16)°. These deviations are attributed to the small bite angle of 79.13 (8)° of the di­imine chelate. The crystal packing exhibits weak inter­molecular hydrogen-bonding inter­actions involving aromatic H atoms, Cl atoms and inter­calated methanol solvent mol­ecules, defining layers parallel to (010).

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.031
• wR factor = 0.066
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         35 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1     ..  C1      ..       3.00 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         27 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Synthesis and crystallization

0.086 g (0.257 mmol, 1 eq.) of PdCl₂(DMSO)₂ and 0.100 g (0.257 mmol, 1 eq.) of N,N'-di(4-methyl­phenyl)-1,2-di­phenyl­ethane-1,2-di­imine were combined with 10 ml of methanol and stirred for 1.5 hours at room temperature. The orange precipitate that formed was collected via vacuum filtration, washed well with water and then air-dried giving 0.0363 g (25%) of the title compound. Slow evaporation of the reaction mixture gave X-ray quality crystals of the title compound. MP: > 532 K. IR (KCl): 3135, 2922, 1514 cm^-1. UV-Vis (λ nm (ε)): 242 (41,200), 264 (34,800), 317 (17,800). TLC (alumina, ethanol): R_f = 0.59.

S2. Refinement

H atoms were placed in idealized positions, guided by difference maps, with C—H bond lengths in the range 0.95-0.98 Å, with U_iso(H) = 1.2U_eq(C) of the attached atom (1.5 for methyl), and thereafter treated as riding. A torsional parameter was refined for each methyl group. The H atom of the methanol solvent molecule was refined with O—H = 0.85 Å and U_iso(H) = 1.5U_eq(O).

Related literature

Palladium(II) diimiine complexes have been widely used as polymerization catalysts for α-olefins (Johnson et al., 1995; Popeney & Guan, 2005) and are easily prepared by the reaction of PdCl₂(DMSO)₂ with the diimine of choice (Kubota et al., 2013; Ettedgui & Neumann, 2009; Price et al., 1972). For structural information about related palladium(II) diimine complexes, see: Kubota et al. (2013); Comerlato et al. (2001); Dyakonenko et al. (2015). For structures of other diimines, see: Wang et al. (2012); Zhao et al. (2015).

Structure description

Palladium(II) diimiine complexes have been widely used as polymerization catalysts for α-olefins (Johnson et al., 1995; Popeney & Guan, 2005) and are easily prepared by the reaction of PdCl₂(DMSO)₂ with the diimine of choice (Kubota et al., 2013; Ettedgui & Neumann, 2009; Price et al., 1972). For structural information about related palladium(II) diimine complexes, see: Kubota et al. (2013); Comerlato et al. (2001); Dyakonenko et al. (2015). For structures of other diimines, see: Wang et al. (2012); Zhao et al. (2015).

Synthesis and crystallization

0.086 g (0.257 mmol, 1 eq.) of PdCl₂(DMSO)₂ and 0.100 g (0.257 mmol, 1 eq.) of N,N'-di(4-methyl­phenyl)-1,2-di­phenyl­ethane-1,2-di­imine were combined with 10 ml of methanol and stirred for 1.5 hours at room temperature. The orange precipitate that formed was collected via vacuum filtration, washed well with water and then air-dried giving 0.0363 g (25%) of the title compound. Slow evaporation of the reaction mixture gave X-ray quality crystals of the title compound. MP: > 532 K. IR (KCl): 3135, 2922, 1514 cm^-1. UV-Vis (λ nm (ε)): 242 (41,200), 264 (34,800), 317 (17,800). TLC (alumina, ethanol): R_f = 0.59.

Refinement details

H atoms were placed in idealized positions, guided by difference maps, with C—H bond lengths in the range 0.95-0.98 Å, with U_iso(H) = 1.2U_eq(C) of the attached atom (1.5 for methyl), and thereafter treated as riding. A torsional parameter was refined for each methyl group. The H atom of the methanol solvent molecule was refined with O—H = 0.85 Å and U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular components of the title compound. Displacement ellipsoids are represented at the 50% probability level.
	Fig. 2. Crystal packing in the title compound, with intermolecular hydrogen bonding emphasized as dashed lines.
	Fig. 3. Crystal packing in the title compound as viewed along [100].

[N,N'-Bis(4-methylphenyl)-1,2-diphenylethane-1,2-diimine-κ²N,N']dichloridopalladium(II) methanol monosolvate

Crystal data

[PdCl2(C28H24N2)]·CH4O	Z = 2
Mr = 597.83	F(000) = 608
Triclinic, P1	Dx = 1.518 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8213 (3) Å	Cell parameters from 4900 reflections
b = 12.3364 (3) Å	θ = 2.8–27.5°
c = 12.7697 (4) Å	µ = 0.94 mm^−1
α = 108.992 (2)°	T = 90 K
β = 93.900 (3)°	Plate, orange
γ = 92.457 (3)°	0.18 × 0.10 × 0.06 mm
V = 1307.83 (7) Å^3

Data collection

Bruker Kappa APEXII DUO CCD diffractometer	5965 independent reflections
Radiation source: fine-focus sealed tube	5026 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −11→11
Tmin = 0.831, Tmax = 0.946	k = −16→16
12258 measured reflections	l = −16→16

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0243P)^2 + 0.2447P] where P = (Fo^2 + 2Fc^2)/3
5965 reflections	(Δ/σ)max = 0.002
322 parameters	Δρmax = 0.57 e Å^−3
1 restraint	Δρmin = −0.64 e Å^−3

Special details

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

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

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

	x	y	z	Uiso*/Ueq
Pd1	0.72678 (2)	0.502582 (15)	0.508729 (15)	0.00896 (6)
Cl1	0.66581 (7)	0.51705 (5)	0.33726 (5)	0.01389 (13)
Cl2	0.78558 (7)	0.31784 (5)	0.42450 (5)	0.01609 (14)
N1	0.7550 (2)	0.49790 (16)	0.66557 (16)	0.0092 (4)
N2	0.6911 (2)	0.66555 (16)	0.59660 (16)	0.0102 (4)
C1	0.7157 (3)	0.5882 (2)	0.7421 (2)	0.0109 (5)
C2	0.6855 (3)	0.6871 (2)	0.7029 (2)	0.0114 (5)
C3	0.8034 (3)	0.39982 (19)	0.69323 (19)	0.0110 (5)
C4	0.9500 (3)	0.3682 (2)	0.67176 (19)	0.0125 (5)
H4	1.0122	0.4074	0.6357	0.015*
C5	1.0047 (3)	0.2789 (2)	0.7035 (2)	0.0151 (5)
H5	1.1058	0.2580	0.6900	0.018*
C6	0.9146 (3)	0.2192 (2)	0.7545 (2)	0.0150 (5)
C7	0.7650 (3)	0.2482 (2)	0.7692 (2)	0.0163 (6)
H7	0.7002	0.2054	0.8002	0.020*
C8	0.7082 (3)	0.3385 (2)	0.7394 (2)	0.0130 (5)
H8	0.6060	0.3578	0.7505	0.016*
C9	0.9798 (3)	0.1291 (2)	0.7979 (2)	0.0226 (6)
H9A	1.0674	0.0985	0.7573	0.034*
H9B	0.9018	0.0667	0.7874	0.034*
H9C	1.0126	0.1639	0.8773	0.034*
C10	0.7048 (3)	0.59987 (19)	0.8604 (2)	0.0112 (5)
C11	0.8257 (3)	0.5791 (2)	0.9252 (2)	0.0142 (5)
H11	0.9185	0.5560	0.8937	0.017*
C12	0.8109 (3)	0.5920 (2)	1.0360 (2)	0.0186 (6)
H12	0.8943	0.5789	1.0805	0.022*
C13	0.6756 (3)	0.6238 (2)	1.0820 (2)	0.0212 (6)
H13	0.6658	0.6318	1.1577	0.025*
C14	0.5547 (3)	0.6441 (2)	1.0180 (2)	0.0184 (6)
H14	0.4616	0.6654	1.0496	0.022*
C15	0.5689 (3)	0.6334 (2)	0.9075 (2)	0.0155 (5)
H15	0.4862	0.6488	0.8641	0.019*
C16	0.6638 (3)	0.8028 (2)	0.78122 (19)	0.0117 (5)
C17	0.5369 (3)	0.8595 (2)	0.7631 (2)	0.0158 (5)
H17	0.4630	0.8228	0.7029	0.019*
C18	0.5185 (3)	0.9697 (2)	0.8332 (2)	0.0192 (6)
H18	0.4316	1.0084	0.8210	0.023*
C19	0.6264 (3)	1.0236 (2)	0.9210 (2)	0.0211 (6)
H19	0.6145	1.0997	0.9681	0.025*
C20	0.7514 (3)	0.9665 (2)	0.9400 (2)	0.0192 (6)
H20	0.8244	1.0031	1.0010	0.023*
C21	0.7709 (3)	0.8564 (2)	0.8709 (2)	0.0155 (5)
H21	0.8568	0.8175	0.8844	0.019*
C22	0.6995 (3)	0.75880 (19)	0.55233 (19)	0.0107 (5)
C23	0.5828 (3)	0.7719 (2)	0.4801 (2)	0.0130 (5)
H23	0.4960	0.7188	0.4581	0.016*
C24	0.5944 (3)	0.8638 (2)	0.4402 (2)	0.0141 (5)
H24	0.5146	0.8734	0.3908	0.017*
C25	0.7211 (3)	0.9422 (2)	0.4715 (2)	0.0136 (5)
C26	0.8371 (3)	0.9256 (2)	0.5424 (2)	0.0149 (5)
H26	0.9243	0.9783	0.5640	0.018*
C27	0.8288 (3)	0.8339 (2)	0.5825 (2)	0.0135 (5)
H27	0.9101	0.8227	0.6298	0.016*
C28	0.7325 (3)	1.0438 (2)	0.4304 (2)	0.0200 (6)
H28A	0.8004	1.0280	0.3704	0.030*
H28B	0.7734	1.1122	0.4917	0.030*
H28C	0.6311	1.0572	0.4026	0.030*
O1	0.9588 (2)	0.31675 (18)	0.21549 (16)	0.0275 (5)
H10H	0.916 (4)	0.333 (3)	0.274 (2)	0.041*
C29	0.8406 (3)	0.2883 (3)	0.1302 (2)	0.0322 (8)
H29A	0.7635	0.2362	0.1441	0.048*
H29B	0.8815	0.2505	0.0589	0.048*
H29C	0.7942	0.3584	0.1281	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.01082 (10)	0.00890 (9)	0.00697 (10)	−0.00045 (7)	0.00080 (7)	0.00251 (7)
Cl1	0.0166 (3)	0.0163 (3)	0.0086 (3)	0.0014 (2)	−0.0004 (2)	0.0042 (2)
Cl2	0.0252 (4)	0.0101 (3)	0.0123 (3)	0.0019 (2)	0.0020 (3)	0.0027 (2)
N1	0.0083 (10)	0.0103 (10)	0.0096 (10)	−0.0003 (8)	0.0001 (8)	0.0045 (8)
N2	0.0105 (10)	0.0094 (10)	0.0110 (10)	0.0014 (8)	0.0002 (8)	0.0037 (8)
C1	0.0070 (12)	0.0140 (12)	0.0120 (12)	−0.0020 (9)	−0.0010 (9)	0.0055 (10)
C2	0.0091 (12)	0.0126 (12)	0.0123 (12)	0.0010 (9)	0.0012 (9)	0.0037 (10)
C3	0.0153 (13)	0.0085 (11)	0.0076 (12)	0.0006 (9)	−0.0016 (9)	0.0010 (10)
C4	0.0135 (13)	0.0141 (12)	0.0084 (12)	0.0003 (10)	0.0008 (10)	0.0018 (10)
C5	0.0147 (13)	0.0171 (13)	0.0103 (13)	0.0046 (10)	0.0010 (10)	−0.0001 (10)
C6	0.0247 (15)	0.0090 (12)	0.0095 (12)	0.0046 (10)	−0.0028 (10)	0.0012 (10)
C7	0.0227 (15)	0.0134 (13)	0.0132 (13)	−0.0013 (11)	0.0033 (11)	0.0049 (11)
C8	0.0138 (13)	0.0131 (12)	0.0106 (12)	−0.0003 (10)	0.0001 (10)	0.0021 (10)
C9	0.0314 (16)	0.0203 (14)	0.0182 (15)	0.0105 (12)	0.0013 (12)	0.0083 (12)
C10	0.0138 (13)	0.0089 (12)	0.0107 (12)	−0.0005 (9)	0.0001 (10)	0.0034 (10)
C11	0.0149 (13)	0.0133 (12)	0.0146 (13)	0.0036 (10)	0.0001 (10)	0.0051 (10)
C12	0.0244 (15)	0.0172 (14)	0.0121 (13)	−0.0012 (11)	−0.0066 (11)	0.0038 (11)
C13	0.0306 (16)	0.0221 (14)	0.0113 (13)	−0.0031 (12)	0.0034 (12)	0.0066 (11)
C14	0.0190 (14)	0.0204 (14)	0.0150 (14)	−0.0001 (11)	0.0052 (11)	0.0041 (11)
C15	0.0183 (14)	0.0142 (13)	0.0142 (13)	0.0002 (10)	−0.0001 (10)	0.0053 (11)
C16	0.0159 (13)	0.0110 (12)	0.0087 (12)	0.0009 (10)	0.0025 (10)	0.0036 (10)
C17	0.0188 (14)	0.0179 (13)	0.0114 (13)	0.0026 (10)	0.0016 (10)	0.0057 (11)
C18	0.0222 (15)	0.0187 (14)	0.0194 (14)	0.0086 (11)	0.0055 (11)	0.0084 (12)
C19	0.0324 (17)	0.0136 (13)	0.0165 (14)	0.0031 (12)	0.0103 (12)	0.0023 (11)
C20	0.0252 (15)	0.0165 (13)	0.0124 (13)	−0.0042 (11)	0.0004 (11)	0.0010 (11)
C21	0.0182 (14)	0.0166 (13)	0.0127 (13)	0.0018 (10)	0.0011 (10)	0.0062 (11)
C22	0.0162 (13)	0.0079 (11)	0.0085 (12)	0.0031 (9)	0.0045 (10)	0.0023 (9)
C23	0.0132 (13)	0.0139 (12)	0.0105 (12)	0.0011 (10)	0.0014 (10)	0.0021 (10)
C24	0.0138 (13)	0.0173 (13)	0.0119 (13)	0.0056 (10)	0.0008 (10)	0.0052 (11)
C25	0.0179 (13)	0.0119 (12)	0.0125 (13)	0.0044 (10)	0.0063 (10)	0.0046 (10)
C26	0.0148 (13)	0.0138 (13)	0.0170 (14)	−0.0003 (10)	0.0031 (10)	0.0063 (11)
C27	0.0138 (13)	0.0178 (13)	0.0093 (12)	0.0002 (10)	−0.0004 (10)	0.0053 (10)
C28	0.0232 (15)	0.0182 (14)	0.0243 (15)	0.0064 (11)	0.0077 (12)	0.0129 (12)
O1	0.0199 (11)	0.0366 (12)	0.0214 (11)	0.0001 (9)	0.0066 (9)	0.0027 (10)
C29	0.0231 (17)	0.0367 (18)	0.0260 (17)	−0.0004 (13)	0.0067 (13)	−0.0050 (14)

Geometric parameters (Å, º)

Pd1—N2	2.0086 (19)	C14—C15	1.388 (3)
Pd1—N1	2.0211 (19)	C14—H14	0.9500
Pd1—Cl2	2.2807 (6)	C15—H15	0.9500
Pd1—Cl1	2.2842 (6)	C16—C17	1.390 (4)
N1—C1	1.299 (3)	C16—C21	1.396 (3)
N1—C3	1.440 (3)	C17—C18	1.386 (4)
N2—C2	1.300 (3)	C17—H17	0.9500
N2—C22	1.439 (3)	C18—C19	1.386 (4)
C1—C10	1.480 (3)	C18—H18	0.9500
C1—C2	1.489 (3)	C19—C20	1.383 (4)
C2—C16	1.481 (3)	C19—H19	0.9500
C3—C4	1.386 (3)	C20—C21	1.383 (4)
C3—C8	1.390 (3)	C20—H20	0.9500
C4—C5	1.386 (3)	C21—H21	0.9500
C4—H4	0.9500	C22—C23	1.386 (3)
C5—C6	1.389 (3)	C22—C27	1.387 (3)
C5—H5	0.9500	C23—C24	1.388 (3)
C6—C7	1.392 (4)	C23—H23	0.9500
C6—C9	1.512 (3)	C24—C25	1.392 (3)
C7—C8	1.390 (3)	C24—H24	0.9500
C7—H7	0.9500	C25—C26	1.386 (4)
C8—H8	0.9500	C25—C28	1.511 (3)
C9—H9A	0.9800	C26—C27	1.387 (3)
C9—H9B	0.9800	C26—H26	0.9500
C9—H9C	0.9800	C27—H27	0.9500
C10—C11	1.389 (3)	C28—H28A	0.9800
C10—C15	1.396 (3)	C28—H28B	0.9800
C11—C12	1.387 (3)	C28—H28C	0.9800
C11—H11	0.9500	O1—C29	1.400 (4)
C12—C13	1.382 (4)	O1—H10H	0.831 (17)
C12—H12	0.9500	C29—H29A	0.9800
C13—C14	1.380 (4)	C29—H29B	0.9800
C13—H13	0.9500	C29—H29C	0.9800
N2—Pd1—N1	79.13 (8)	C13—C14—H14	119.9
N2—Pd1—Cl2	173.82 (6)	C15—C14—H14	119.9
N1—Pd1—Cl2	95.67 (6)	C14—C15—C10	119.9 (2)
N2—Pd1—Cl1	96.49 (6)	C14—C15—H15	120.0
N1—Pd1—Cl1	172.74 (6)	C10—C15—H15	120.0
Cl2—Pd1—Cl1	89.02 (2)	C17—C16—C21	119.8 (2)
C1—N1—C3	120.6 (2)	C17—C16—C2	119.3 (2)
C1—N1—Pd1	115.20 (17)	C21—C16—C2	120.8 (2)
C3—N1—Pd1	124.03 (15)	C18—C17—C16	119.9 (2)
C2—N2—C22	119.9 (2)	C18—C17—H17	120.1
C2—N2—Pd1	115.61 (16)	C16—C17—H17	120.1
C22—N2—Pd1	123.53 (15)	C19—C18—C17	120.2 (3)
N1—C1—C10	125.8 (2)	C19—C18—H18	119.9
N1—C1—C2	114.2 (2)	C17—C18—H18	119.9
C10—C1—C2	120.0 (2)	C20—C19—C18	119.9 (2)
N2—C2—C16	123.2 (2)	C20—C19—H19	120.1
N2—C2—C1	114.7 (2)	C18—C19—H19	120.1
C16—C2—C1	121.9 (2)	C19—C20—C21	120.5 (3)
C4—C3—C8	120.8 (2)	C19—C20—H20	119.8
C4—C3—N1	117.3 (2)	C21—C20—H20	119.8
C8—C3—N1	121.9 (2)	C20—C21—C16	119.7 (3)
C3—C4—C5	119.2 (2)	C20—C21—H21	120.1
C3—C4—H4	120.4	C16—C21—H21	120.1
C5—C4—H4	120.4	C23—C22—C27	121.0 (2)
C4—C5—C6	121.3 (2)	C23—C22—N2	120.8 (2)
C4—C5—H5	119.4	C27—C22—N2	118.1 (2)
C6—C5—H5	119.4	C22—C23—C24	119.1 (2)
C5—C6—C7	118.3 (2)	C22—C23—H23	120.5
C5—C6—C9	120.8 (2)	C24—C23—H23	120.5
C7—C6—C9	120.8 (2)	C23—C24—C25	121.1 (2)
C8—C7—C6	121.4 (2)	C23—C24—H24	119.5
C8—C7—H7	119.3	C25—C24—H24	119.5
C6—C7—H7	119.3	C26—C25—C24	118.5 (2)
C3—C8—C7	118.8 (2)	C26—C25—C28	120.3 (2)
C3—C8—H8	120.6	C24—C25—C28	121.2 (2)
C7—C8—H8	120.6	C25—C26—C27	121.5 (2)
C6—C9—H9A	109.5	C25—C26—H26	119.2
C6—C9—H9B	109.5	C27—C26—H26	119.2
H9A—C9—H9B	109.5	C26—C27—C22	118.8 (2)
C6—C9—H9C	109.5	C26—C27—H27	120.6
H9A—C9—H9C	109.5	C22—C27—H27	120.6
H9B—C9—H9C	109.5	C25—C28—H28A	109.5
C11—C10—C15	119.5 (2)	C25—C28—H28B	109.5
C11—C10—C1	121.9 (2)	H28A—C28—H28B	109.5
C15—C10—C1	118.6 (2)	C25—C28—H28C	109.5
C12—C11—C10	119.9 (2)	H28A—C28—H28C	109.5
C12—C11—H11	120.0	H28B—C28—H28C	109.5
C10—C11—H11	120.0	C29—O1—H10H	105 (2)
C13—C12—C11	120.4 (3)	O1—C29—H29A	109.5
C13—C12—H12	119.8	O1—C29—H29B	109.5
C11—C12—H12	119.8	H29A—C29—H29B	109.5
C14—C13—C12	120.0 (2)	O1—C29—H29C	109.5
C14—C13—H13	120.0	H29A—C29—H29C	109.5
C12—C13—H13	120.0	H29B—C29—H29C	109.5
C13—C14—C15	120.2 (3)
N2—Pd1—N1—C1	10.15 (16)	N1—C1—C10—C15	−126.3 (3)
Cl2—Pd1—N1—C1	−173.22 (16)	C2—C1—C10—C15	56.1 (3)
N2—Pd1—N1—C3	−174.59 (18)	C15—C10—C11—C12	−0.2 (3)
Cl2—Pd1—N1—C3	2.04 (17)	C1—C10—C11—C12	179.5 (2)
N1—Pd1—N2—C2	−7.07 (17)	C10—C11—C12—C13	1.0 (4)
Cl1—Pd1—N2—C2	167.06 (16)	C11—C12—C13—C14	−0.7 (4)
N1—Pd1—N2—C22	161.36 (19)	C12—C13—C14—C15	−0.4 (4)
Cl1—Pd1—N2—C22	−24.50 (18)	C13—C14—C15—C10	1.2 (4)
C3—N1—C1—C10	−4.4 (3)	C11—C10—C15—C14	−0.9 (3)
Pd1—N1—C1—C10	171.05 (18)	C1—C10—C15—C14	179.4 (2)
C3—N1—C1—C2	173.36 (19)	N2—C2—C16—C17	56.3 (3)
Pd1—N1—C1—C2	−11.2 (2)	C1—C2—C16—C17	−128.8 (2)
C22—N2—C2—C16	9.6 (3)	N2—C2—C16—C21	−122.0 (3)
Pd1—N2—C2—C16	178.51 (18)	C1—C2—C16—C21	52.8 (3)
C22—N2—C2—C1	−165.5 (2)	C21—C16—C17—C18	1.0 (3)
Pd1—N2—C2—C1	3.3 (3)	C2—C16—C17—C18	−177.4 (2)
N1—C1—C2—N2	5.3 (3)	C16—C17—C18—C19	0.2 (4)
C10—C1—C2—N2	−176.8 (2)	C17—C18—C19—C20	−1.2 (4)
N1—C1—C2—C16	−170.0 (2)	C18—C19—C20—C21	1.0 (4)
C10—C1—C2—C16	7.9 (3)	C19—C20—C21—C16	0.2 (4)
C1—N1—C3—C4	−119.0 (2)	C17—C16—C21—C20	−1.2 (4)
Pd1—N1—C3—C4	66.0 (3)	C2—C16—C21—C20	177.2 (2)
C1—N1—C3—C8	61.1 (3)	C2—N2—C22—C23	−115.9 (3)
Pd1—N1—C3—C8	−113.9 (2)	Pd1—N2—C22—C23	76.1 (3)
C8—C3—C4—C5	−4.1 (4)	C2—N2—C22—C27	65.1 (3)
N1—C3—C4—C5	176.0 (2)	Pd1—N2—C22—C27	−102.8 (2)
C3—C4—C5—C6	1.1 (4)	C27—C22—C23—C24	−1.9 (4)
C4—C5—C6—C7	2.6 (4)	N2—C22—C23—C24	179.2 (2)
C4—C5—C6—C9	−174.5 (2)	C22—C23—C24—C25	0.2 (4)
C5—C6—C7—C8	−3.5 (4)	C23—C24—C25—C26	0.9 (4)
C9—C6—C7—C8	173.6 (2)	C23—C24—C25—C28	−178.6 (2)
C4—C3—C8—C7	3.3 (4)	C24—C25—C26—C27	−0.3 (4)
N1—C3—C8—C7	−176.8 (2)	C28—C25—C26—C27	179.2 (2)
C6—C7—C8—C3	0.6 (4)	C25—C26—C27—C22	−1.3 (4)
N1—C1—C10—C11	54.0 (3)	C23—C22—C27—C26	2.4 (4)
C2—C1—C10—C11	−123.6 (3)	N2—C22—C27—C26	−178.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10H···Cl2	0.83 (2)	2.36 (2)	3.161 (2)	163 (3)
C17—H17···Cl2^i	0.95	2.80	3.708 (3)	161
C21—H21···O1^ii	0.95	2.48	3.275 (3)	141

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.