(2,2'-Bipyridine-[kappa]²N,N')(1,1-cyclobutanedicarboxylato-[kappa]²O,O')palladium(II), (1,1-cyclobutanedicarboxylato-[kappa]²O,O')(1,10-phenanthroline-[kappa]²N,N')palladium(II) monohydrate and (1,1-cyclobutanedicarboxylato-[kappa]²O,O')(1,10-phenanthroline-[kappa]²N,N')palladium(II) dihydrate

In the three title compounds, [Pd(C₆H₆O₄)(C₁₀H₈N₂)], (I), [Pd(C₆H₆O₄)(C₁₂H₈N₂)]·H₂O, (IIa), and [Pd(C₆H₆O₄)(C₁₂H₈N₂)]·2H₂O, (IIb), respectively, each Pd^II atom has a similar distorted cis-planar four-coordination geometry, completed by two O atoms of a bidentate 1,1-cyclo­butane­di­carboxyl­ate anion and two N atoms of either a 2,2'-bi­pyridine or a 1,10-phenanthroline ligand.

S1. Comment

Square-planar Pt^II complexes, such as cisplatin, cis-diamminedichloroplatinum(II), or carboplatin, cis-diammine(1,1-cyclobutanedicarboxylato)platinum(II), have been used as therapeutic anticancer drugs, where carboplatin, with the bidentate 1,1-cyclobutanedicarboxylate (cbdca) ligand, has fewer side effects than cisplatin (Jakupec et al., 2003). The Pd^II analogues of such Pt^II complexes have been used as good models for studies of the chemistry of square-planar complexes (Rau et al., 1996). For example, cis-diammine(1,1-cyclobutanedicarboxylato)palladium(II) (Barnham et al., 1994) is isostructural with carboplatin (Beagley et al., 1985; Neidle et al., 1980). Recently, a palladium complex with an aromatic heterocyclic ligand, [Pd(bpy)(cbdca)] (where bpy is 2,2'-bipyridine), has been shown to have better cytotoxic activity than cisplatin against P₃₈₈ lymphocytic leukemia cells (Mansuri-Torshizi et al., 2001). The aromatic heterocycles can stack with nucleobases and enhance complex formation with DNA, which is the principal target in the chemotherapy of tumours (Shehata, 2001). In this study, we have prepared the Pd^II analogues of carboplatin complexes with the aromatic heterocyclic ligands bpy and 1,10-phenanthroline (phen), and determined the structures of [Pd(bpy)(cbdca)], (I), [Pd(phen)(cbdca)]·H₂O, (IIa), and [Pd(phen)(cbdca)]·2H₂O, (IIb). The results are presented here. \sch

The central Pd atom of each complex has the same distorted cis-square-planer coordination geometry, involving two N atoms of the heterocycle and two O atoms of the cbdca ligand (Figs. 1–3). The bpy plane is mostly perpendicular to the cyclobutane plane. The Pd atom and cbdca ligand form a six-membered chelate ring in a boat conformation, while the aromatic heterocycle ligand makes a planar five-membered chelate ring. In (IIb), there are two independent molecules in the asymmetric unit. The molecular structures of (IIa) and (IIb) are similar to each other.

The bond lengths and angles in (I), (IIa) and (IIb) are very similar to each other (Tables 2, 4 and 6). These values may be compared with those reported for [Pd(NH₃)₂(cbdca)] [(III); Barnham et al., 1994) and [Pd(en)(cbdca)] [(IV); en is ethylenediamine; Tercero et al., 2003). The Pd—N and Pd—O bond lengths in (I), (IIa) and (IIb) are in the ranges 1.991 (5)–2.010 (4) Å and 1.982 (3)–2.005 (4) Å, respectively, which are slightly shorter than those in (III) and (IV) [2.020 (7)–2.030 (2) Å for Pd—N and 2.005 (2)–2.017 (6) Å for Pd—O]. Therefore, the coordination bonds in the title compounds may be somewhat stronger than those in (III) and (IV). The O—Pd—O chelate angles in (I), (IIa) and (IIb) are similar to those observed in (III) and (IV) [90.9° and 92.69 (7)°, respectively]. The bpy N—Pd—N chelate angle in (I), and the phen N—Pd—N chelate angles in (IIa) and (IIb), are slightly smaller than the value of 84.15 (8)° for en in (IV), and much smaller than the NH₃—Pd—NH₃ bond angle of 95.0° in (III).

The crystal structure of (I) is stabilized by stacking interactions between bpy ligands, which are related by a centre of symmetry, with a distance between the planes of 3.685 (2) Å. In (IIa), no stacking interactions between phen ligands are present, and the complexes are connected to each other by hydrogen-bonding networks through disordered water molecules (Table 4). In (IIb), there are stacking interactions between phen ligands related by a centre of symmetry, the distances between the planes being 3.379 (6) and 3.360 (7) Å, for Pd1—Pd1 and Pd2—Pd2 pairs, respectively. Furthermore, complex molecules are connected to each other by hydrogen-bonding networks through the water molecules (Table 5).

S2. Experimental

Compound (I), [Pd(bpy)(cbdca)], was synthesized as follows. First, bpy was reacted with palladium acetate, [Pd(CH₃COOH)₂], for 15 min at room temperature (molar ratio 1:1) in dimethylformamide, then an equimolar amount of 1,1-cyclobutanedicarboxylic acid was added. This mixture was left to stand at room temperature and pale-yellow prism crystals of (I) appeared in a few days. Compound (II), [Pd(phen)(cbdca)], was synthesized using a method similar to that used for (I), except that phen was used in place of bpy. Crystals of the monohydrate, (IIa), appeared in a few days. A small quantity of crystals of the dihydrate, (IIb), appeared in the same crystallizing vessel with (IIa). The crystals of (IIb) are rectangular, thin and plate-like, while those of (IIa) are prisms. The colour of the crystals is pale yellow for both (IIa) and (IIb).

S3. Refinement

For (I), all H atoms were located in difference Fourier maps and were then regenerated at the ideal positions by riding models using HFIX instructions (SHELXL97; Sheldrick, 1997). In (IIa), there is positional disorder of the water molecule over two sites, O5A and O5B. The occupation factors were assigned to 43% and 57%, respectively. For (IIa) and (IIb), all H atoms were located in the difference Fourier maps, and then, except for those of the water molecules, were regenerated at the ideal positions by riding models using HFIX instructions. The H atoms of the water molecules were fixed at the positions located by the difference Fourier maps.

Computing details

For all compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2000). Program(s) used to solve structure: SIR97 (Altomare et al., 1999) for (I); SHELXS97 (Sheldrick, 1997) for (IIa); SHELXS97 (Scheldrick, 1997) for (IIb). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I), (IIa); SHELXL97 (Scheldrick, 1997) for (IIb). For all compounds, molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecular structure of (IIa), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. The molecular structure of (IIb), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

(I) (2,2'-Bipyridine-κ²N,N')(1,1-cyclobutanedicarboxylato- κ²O,O')palladium(II)

Crystal data

[Pd(C6H6O4)(C10H8N2)]	Z = 2
Mr = 404.71	F(000) = 404.0
Triclinic, P1	Dx = 1.857 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 9.087 (1) Å	Cell parameters from 25 reflections
b = 9.440 (1) Å	θ = 14.9–15.0°
c = 9.9820 (9) Å	µ = 1.31 mm^−1
α = 90.458 (9)°	T = 296 K
β = 113.095 (9)°	Prism, yellow
γ = 111.077 (9)°	0.35 × 0.20 × 0.10 mm
V = 723.78 (15) Å^3

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.014
ω/2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −11→11
Tmin = 0.732, Tmax = 0.878	k = 0→12
3512 measured reflections	l = −12→12
3315 independent reflections	3 standard reflections every 150 reflections
3005 reflections with I > 2σ(I)	intensity decay: 0.9%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0245P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.057	(Δ/σ)max = 0.001
S = 1.30	Δρmax = 0.40 e Å^−3
3315 reflections	Δρmin = −0.45 e Å^−3
208 parameters

Special details

Refinement. Refinement using reflections with F² > −10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Pd1	0.58260 (2)	0.10529 (2)	0.39803 (2)	0.02665 (6)
O1	0.7302 (2)	−0.0082 (2)	0.5044 (2)	0.0342 (4)
O2	0.9642 (3)	−0.0003 (2)	0.6939 (2)	0.0491 (5)
O3	0.6978 (2)	0.2716 (2)	0.5754 (2)	0.0345 (4)
O4	0.9308 (2)	0.4054 (2)	0.7777 (2)	0.0501 (5)
N1	0.4527 (2)	−0.0496 (2)	0.2113 (2)	0.0288 (4)
N2	0.4191 (2)	0.1991 (2)	0.2784 (2)	0.0288 (4)
C2	0.3338 (3)	−0.0161 (3)	0.0986 (3)	0.0308 (5)
C3	0.2395 (3)	−0.1116 (3)	−0.0372 (3)	0.0406 (6)
C4	0.2665 (4)	−0.2443 (3)	−0.0573 (3)	0.0473 (7)
C5	0.3867 (4)	−0.2769 (3)	0.0586 (3)	0.0442 (6)
C6	0.4777 (3)	−0.1779 (3)	0.1921 (3)	0.0373 (5)
C12	0.3139 (3)	0.1252 (3)	0.1374 (2)	0.0298 (5)
C13	0.1952 (3)	0.1790 (3)	0.0428 (3)	0.0393 (5)
C14	0.1854 (3)	0.3107 (3)	0.0944 (3)	0.0416 (6)
C15	0.2904 (3)	0.3831 (3)	0.2391 (3)	0.0413 (6)
C16	0.4054 (3)	0.3233 (3)	0.3287 (3)	0.0348 (5)
C17	0.8850 (3)	0.0656 (3)	0.6081 (2)	0.0311 (5)
C18	0.8615 (3)	0.3128 (3)	0.6641 (2)	0.0298 (5)
C19	0.9643 (3)	0.2401 (3)	0.6184 (2)	0.0289 (4)
C20	0.9851 (3)	0.2878 (3)	0.4744 (3)	0.0379 (5)
C21	1.1816 (4)	0.3537 (4)	0.5624 (4)	0.0592 (8)
C22	1.1638 (3)	0.3179 (3)	0.7063 (3)	0.0440 (6)
H3	0.1587	−0.0874	−0.1144	0.0488*
H4	0.2040	−0.3103	−0.1482	0.0568*
H5	0.4066	−0.3652	0.0469	0.0530*
H6	0.5584	−0.2009	0.2706	0.0448*
H13	0.1231	0.1276	−0.0539	0.0471*
H14	0.1084	0.3499	0.0317	0.0499*
H15	0.2841	0.4706	0.2758	0.0495*
H16	0.4754	0.3709	0.4268	0.0417*
H20A	0.9415	0.2011	0.3969	0.0455*
H20B	0.9391	0.3646	0.4363	0.0455*
H21A	1.2369	0.4630	0.5633	0.0710*
H21B	1.2377	0.2971	0.5332	0.0710*
H22A	1.2024	0.4091	0.7770	0.0528*
H22B	1.2165	0.2478	0.7526	0.0528*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0245 (1)	0.0295 (1)	0.02334 (9)	0.01352 (7)	0.00500 (7)	0.00398 (6)
O1	0.0329 (9)	0.0308 (8)	0.0332 (9)	0.0168 (7)	0.0045 (7)	0.0058 (7)
O2	0.053 (1)	0.042 (1)	0.0373 (10)	0.0290 (9)	−0.0042 (8)	0.0062 (8)
O3	0.0317 (8)	0.0413 (9)	0.0290 (8)	0.0208 (7)	0.0058 (7)	−0.0005 (7)
O4	0.044 (1)	0.059 (1)	0.039 (1)	0.0290 (10)	0.0015 (8)	−0.0147 (9)
N1	0.0273 (9)	0.0288 (9)	0.0271 (9)	0.0115 (8)	0.0079 (8)	0.0050 (7)
N2	0.0261 (9)	0.0330 (10)	0.0278 (9)	0.0152 (8)	0.0087 (7)	0.0071 (8)
C2	0.028 (1)	0.032 (1)	0.028 (1)	0.0107 (9)	0.0082 (9)	0.0056 (9)
C3	0.040 (1)	0.043 (1)	0.028 (1)	0.016 (1)	0.003 (1)	0.003 (1)
C4	0.053 (2)	0.038 (1)	0.035 (1)	0.014 (1)	0.006 (1)	−0.005 (1)
C5	0.054 (2)	0.032 (1)	0.043 (1)	0.020 (1)	0.015 (1)	0.003 (1)
C6	0.040 (1)	0.036 (1)	0.034 (1)	0.019 (1)	0.010 (1)	0.0069 (10)
C12	0.027 (1)	0.031 (1)	0.029 (1)	0.0115 (9)	0.0094 (9)	0.0080 (9)
C13	0.035 (1)	0.044 (1)	0.031 (1)	0.018 (1)	0.0041 (10)	0.008 (1)
C14	0.037 (1)	0.046 (1)	0.043 (1)	0.025 (1)	0.009 (1)	0.017 (1)
C15	0.043 (1)	0.042 (1)	0.047 (1)	0.027 (1)	0.017 (1)	0.009 (1)
C16	0.031 (1)	0.038 (1)	0.035 (1)	0.017 (1)	0.0104 (10)	0.0037 (10)
C17	0.034 (1)	0.036 (1)	0.025 (1)	0.022 (1)	0.0079 (9)	0.0043 (9)
C18	0.032 (1)	0.031 (1)	0.024 (1)	0.0174 (10)	0.0062 (9)	0.0038 (9)
C19	0.027 (1)	0.033 (1)	0.026 (1)	0.0153 (9)	0.0076 (9)	0.0031 (9)
C20	0.047 (1)	0.036 (1)	0.038 (1)	0.020 (1)	0.022 (1)	0.009 (1)
C21	0.044 (2)	0.063 (2)	0.077 (2)	0.022 (1)	0.032 (2)	0.030 (2)
C22	0.030 (1)	0.047 (2)	0.048 (2)	0.016 (1)	0.010 (1)	−0.005 (1)

Geometric parameters (Å, º)

Pd1—O1	2.002 (2)	C12—C13	1.384 (4)
Pd1—O3	2.004 (2)	C13—C14	1.388 (5)
Pd1—N1	1.999 (2)	C13—H13	0.930
Pd1—N2	1.998 (2)	C14—C15	1.377 (3)
O1—C17	1.295 (2)	C14—H14	0.930
O2—C17	1.219 (3)	C15—C16	1.382 (4)
O3—C18	1.301 (3)	C15—H15	0.930
O4—C18	1.214 (3)	C16—H16	0.930
N1—C2	1.353 (3)	C17—C19	1.526 (3)
N1—C6	1.335 (4)	C18—C19	1.530 (4)
N2—C12	1.353 (3)	C19—C20	1.571 (4)
N2—C16	1.336 (4)	C19—C22	1.543 (3)
C2—C3	1.377 (3)	C20—C21	1.520 (4)
C2—C12	1.477 (4)	C20—H20A	0.970
C3—C4	1.388 (5)	C20—H20B	0.970
C3—H3	0.930	C21—C22	1.534 (5)
C4—C5	1.372 (4)	C21—H21A	0.970
C4—H4	0.930	C21—H21B	0.970
C5—C6	1.376 (3)	C22—H22A	0.970
C5—H5	0.930	C22—H22B	0.970
C6—H6	0.930
Pd1···O1^i	3.191 (2)	O2···C16^i	3.558 (3)
Pd1···Pd1^i	3.2658 (4)	O3···C6^i	3.261 (4)
O1···N2^i	3.225 (3)	O3···N1^i	3.330 (3)
O1···C16^i	3.492 (3)	O4···C15^iv	3.268 (4)
O1···O3^i	3.539 (2)	O4···C4^v	3.416 (3)
O2···C13^ii	3.319 (3)	O4···C14^ii	3.456 (3)
O2···C3^ii	3.352 (3)	N2···C17^i	3.564 (3)
O2···N2^i	3.434 (3)	C3···C14^vi	3.435 (4)
O2···C20^iii	3.441 (4)	C13···C22^vii	3.560 (4)
O2···C12^i	3.441 (4)
O1—Pd1—O3	91.68 (7)	C15—C14—H14	120.2
O1—Pd1—N1	93.94 (8)	C14—C15—C16	118.7 (3)
O1—Pd1—N2	174.40 (6)	C14—C15—H15	120.6
O3—Pd1—N1	174.37 (9)	C16—C15—H15	120.7
O3—Pd1—N2	93.57 (8)	N2—C16—C15	121.9 (2)
N1—Pd1—N2	80.80 (8)	N2—C16—H16	119.0
Pd1—O1—C17	120.5 (2)	C15—C16—H16	119.0
Pd1—O3—C18	120.8 (2)	O1—C17—O2	121.9 (2)
Pd1—N1—C2	115.3 (2)	O1—C17—C19	116.8 (2)
Pd1—N1—C6	124.8 (1)	O2—C17—C19	121.3 (2)
C2—N1—C6	119.9 (2)	O3—C18—O4	121.9 (3)
Pd1—N2—C12	115.2 (2)	O3—C18—C19	117.0 (2)
Pd1—N2—C16	125.0 (1)	O4—C18—C19	121.2 (2)
C12—N2—C16	119.8 (2)	C17—C19—C18	109.5 (2)
N1—C2—C3	120.8 (3)	C17—C19—C20	112.6 (2)
N1—C2—C12	114.1 (2)	C17—C19—C22	115.4 (2)
C3—C2—C12	125.0 (2)	C18—C19—C20	113.9 (2)
C2—C3—C4	119.2 (2)	C18—C19—C22	115.1 (2)
C2—C3—H3	120.4	C20—C19—C22	89.3 (2)
C4—C3—H3	120.4	C19—C20—C21	89.2 (2)
C3—C4—C5	119.1 (2)	C19—C20—H20A	113.8
C3—C4—H4	120.5	C19—C20—H20B	113.8
C5—C4—H4	120.5	C21—C20—H20A	113.8
C4—C5—C6	119.6 (3)	C21—C20—H20B	113.8
C4—C5—H5	120.2	H20A—C20—H20B	111.0
C6—C5—H5	120.2	C20—C21—C22	91.5 (3)
N1—C6—C5	121.4 (2)	C20—C21—H21A	113.4
N1—C6—H6	119.3	C20—C21—H21B	113.4
C5—C6—H6	119.3	C22—C21—H21A	113.4
N2—C12—C2	114.5 (2)	C22—C21—H21B	113.4
N2—C12—C13	120.8 (3)	H21A—C21—H21B	110.7
C2—C12—C13	124.7 (2)	C19—C22—C21	89.8 (2)
C12—C13—C14	119.0 (2)	C19—C22—H22A	113.7
C12—C13—H13	120.5	C19—C22—H22B	113.7
C14—C13—H13	120.5	C21—C22—H22A	113.7
C13—C14—C15	119.6 (3)	C21—C22—H22B	113.7
C13—C14—H14	120.2	H22A—C22—H22B	110.9
Pd1—O1—C17—O2	165.3 (2)	N1—C2—C12—N2	0.8 (3)
Pd1—O1—C17—C19	−14.6 (3)	N1—C2—C12—C13	−177.0 (3)
Pd1—O3—C18—O4	−174.8 (2)	N1—C6—C5—C4	−0.6 (5)
Pd1—O3—C18—C19	5.8 (3)	N2—Pd1—O3—C18	−148.4 (2)
Pd1—N1—C2—C3	178.1 (2)	N2—Pd1—N1—C2	3.8 (2)
Pd1—N1—C2—C12	−3.6 (3)	N2—Pd1—N1—C6	−177.1 (2)
Pd1—N1—C6—C5	−178.0 (2)	N2—C12—C2—C3	179.0 (3)
Pd1—N2—C12—C2	2.4 (3)	N2—C12—C13—C14	0.1 (4)
Pd1—N2—C12—C13	−179.7 (2)	N2—C16—C15—C14	1.0 (4)
Pd1—N2—C16—C15	179.3 (2)	C2—N1—C6—C5	1.1 (4)
O1—Pd1—O3—C18	33.6 (2)	C2—C3—C4—C5	−0.1 (5)
O1—Pd1—N1—C2	−178.2 (2)	C2—C12—N2—C16	−176.1 (2)
O1—Pd1—N1—C6	0.9 (2)	C2—C12—C13—C14	177.8 (3)
O1—C17—C19—C18	66.9 (3)	C3—C2—N1—C6	−1.1 (4)
O1—C17—C19—C20	−60.9 (3)	C3—C2—C12—C13	1.2 (4)
O1—C17—C19—C22	−161.4 (3)	C3—C4—C5—C6	0.1 (5)
O2—C17—C19—C18	−113.0 (3)	C4—C3—C2—C12	−177.6 (3)
O2—C17—C19—C20	119.2 (3)	C6—N1—C2—C12	177.3 (2)
O2—C17—C19—C22	18.7 (4)	C12—N2—C16—C15	−2.4 (4)
O3—Pd1—O1—C17	−28.8 (2)	C12—C13—C14—C15	−1.5 (4)
O3—Pd1—N2—C12	176.7 (2)	C13—C12—N2—C16	1.8 (4)
O3—Pd1—N2—C16	−4.9 (2)	C13—C14—C15—C16	1.0 (4)
O3—C18—C19—C17	−61.4 (3)	C17—C19—C20—C21	−113.7 (3)
O3—C18—C19—C20	65.7 (2)	C17—C19—C22—C21	111.2 (3)
O3—C18—C19—C22	166.7 (2)	C18—C19—C20—C21	120.8 (2)
O4—C18—C19—C17	119.2 (2)	C18—C19—C22—C21	−119.7 (3)
O4—C18—C19—C20	−113.7 (2)	C19—C20—C21—C22	−3.6 (2)
O4—C18—C19—C22	−12.7 (3)	C19—C22—C21—C20	3.7 (3)
N1—Pd1—O1—C17	151.4 (2)	C20—C19—C22—C21	−3.5 (2)
N1—Pd1—N2—C12	−3.3 (2)	C21—C20—C19—C22	3.6 (2)
N1—Pd1—N2—C16	175.0 (2)	C21—C20—C19—C22	3.6 (2)
N1—C2—C3—C4	0.6 (4)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z+1; (iii) −x+2, −y, −z+1; (iv) −x+1, −y+1, −z+1; (v) x+1, y+1, z+1; (vi) −x, −y, −z; (vii) x−1, y, z−1.

(IIa) (1,1-cyclobutanedicarboxylato-κ²O,O') (1,10-phenanthroline-κ²N,N')palladium(II) monohydrate

Crystal data

[Pd(C6H6O4)(C12H8N2)]·H2O	F(000) = 896
Mr = 446.75	Dx = 1.733 Mg m^−3
Orthorhombic, Pnn2	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2 -2n	Cell parameters from 25 reflections
a = 17.219 (2) Å	θ = 14.7–15.0°
b = 18.875 (2) Å	µ = 1.12 mm^−1
c = 5.268 (2) Å	T = 296 K
V = 1712.2 (7) Å^3	Prism, pale yellow
Z = 4	0.50 × 0.30 × 0.20 mm

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.000
ω/2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→22
Tmin = 0.736, Tmax = 0.800	k = 0→24
2177 measured reflections	l = 0→6
2177 independent reflections	3 standard reflections every 150 reflections
1839 reflections with I > 2σ(I)	intensity decay: 0.8%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0254P)^2 + 2.17P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.028	(Δ/σ)max = 0.001
wR(F^2) = 0.079	Δρmax = 0.51 e Å^−3
S = 1.20	Δρmin = −0.60 e Å^−3
2177 reflections	Absolute structure: Flack (1983), no Friedel pairs
244 parameters	Absolute structure parameter: 0.17 (6)
H-atom parameters constrained

Special details

Refinement. Refinement using reflections with F² > −10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pd1	0.28978 (2)	0.27335 (2)	0.4658 (1)	0.0371 (1)
O1	0.1985 (2)	0.2533 (2)	0.6899 (10)	0.0432 (10)
O2	0.1103 (2)	0.2910 (2)	0.958 (2)	0.054 (1)
O3	0.3230 (2)	0.3540 (2)	0.6884 (9)	0.048 (1)
O4	0.2915 (2)	0.4405 (2)	0.958 (2)	0.060 (1)
O5A	0.4494 (9)	0.4814 (9)	0.683 (7)	0.17 (1)	0.43
O5B	0.4273 (5)	0.5093 (6)	1.081 (5)	0.18 (1)	0.57
N1	0.2672 (3)	0.1914 (2)	0.239 (1)	0.040 (1)
N2	0.3833 (3)	0.2810 (3)	0.244 (1)	0.039 (1)
C1	0.2064 (3)	0.1480 (3)	0.243 (2)	0.048 (2)
C2	0.1990 (4)	0.0940 (4)	0.067 (2)	0.058 (2)
C3	0.2538 (4)	0.0831 (3)	−0.116 (1)	0.051 (2)
C4	0.3202 (3)	0.1273 (3)	−0.120 (1)	0.043 (1)
C5	0.3229 (3)	0.1811 (3)	0.061 (1)	0.038 (1)
C6	0.3862 (3)	0.2298 (3)	0.066 (1)	0.036 (1)
C7	0.4467 (3)	0.2237 (3)	−0.111 (1)	0.038 (1)
C8	0.5068 (3)	0.2744 (4)	−0.093 (1)	0.055 (2)
C9	0.5027 (4)	0.3250 (4)	0.090 (2)	0.061 (2)
C10	0.4407 (4)	0.3281 (3)	0.255 (1)	0.051 (2)
C11	0.3832 (4)	0.1215 (3)	−0.298 (1)	0.047 (1)
C12	0.4439 (3)	0.1681 (3)	−0.293 (1)	0.045 (1)
C13	0.1624 (3)	0.3027 (3)	0.808 (1)	0.036 (1)
C14	0.1865 (3)	0.3797 (3)	0.745 (1)	0.036 (1)
C15	0.2721 (3)	0.3925 (3)	0.805 (1)	0.040 (1)
C16	0.1620 (3)	0.3981 (3)	0.468 (2)	0.042 (1)
C17	0.1290 (4)	0.4371 (4)	0.840 (1)	0.048 (2)
C18	0.0938 (4)	0.4402 (4)	0.571 (2)	0.061 (2)
H1	0.1682	0.1540	0.3654	0.0577*
H2	0.1557	0.0645	0.0730	0.0694*
H3	0.2478	0.0473	−0.2357	0.0617*
H5AA	0.3960	0.4690	0.7760	0.0507*	0.43
H5AB	0.4420	0.4910	0.4870	0.0507*	0.43
H5BB	0.4680	0.5120	0.9480	0.0507*	0.57
H5BA	0.3820	0.4860	1.0380	0.0507*	0.57
H8	0.5485	0.2733	−0.2048	0.0655*
H9	0.5424	0.3581	0.1041	0.0737*
H10	0.4389	0.3638	0.3761	0.0615*
H11	0.3826	0.0854	−0.4180	0.0560*
H12	0.4838	0.1635	−0.4108	0.0539*
H16A	0.1997	0.4267	0.3778	0.0508*
H16B	0.1469	0.3571	0.3685	0.0508*
H17A	0.0931	0.4203	0.9685	0.0574*
H17B	0.1539	0.4808	0.8923	0.0574*
H18A	0.0444	0.4157	0.5566	0.0727*
H18B	0.0902	0.4878	0.5031	0.0727*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0331 (2)	0.0419 (2)	0.0362 (2)	0.0063 (2)	0.0095 (3)	−0.0001 (4)
O1	0.047 (2)	0.034 (2)	0.049 (3)	0.002 (2)	0.019 (2)	0.001 (2)
O2	0.053 (2)	0.055 (2)	0.055 (3)	−0.006 (2)	0.032 (4)	0.001 (4)
O3	0.034 (2)	0.065 (3)	0.046 (3)	0.002 (2)	0.003 (2)	−0.012 (2)
O4	0.054 (2)	0.059 (2)	0.067 (3)	−0.009 (2)	−0.005 (4)	−0.018 (5)
O5A	0.057 (9)	0.09 (1)	0.36 (4)	−0.013 (8)	−0.05 (2)	0.08 (2)
O5B	0.033 (4)	0.054 (6)	0.46 (4)	−0.017 (4)	0.05 (1)	−0.05 (1)
N1	0.038 (2)	0.038 (2)	0.044 (3)	0.006 (2)	0.008 (2)	0.003 (2)
N2	0.033 (2)	0.047 (3)	0.038 (3)	0.003 (2)	0.008 (2)	0.000 (2)
C1	0.041 (3)	0.043 (3)	0.061 (4)	0.003 (3)	0.011 (3)	0.007 (3)
C2	0.049 (4)	0.049 (4)	0.076 (5)	−0.006 (3)	0.004 (4)	0.005 (4)
C3	0.055 (4)	0.035 (3)	0.064 (5)	0.004 (3)	0.002 (3)	−0.002 (3)
C4	0.043 (3)	0.038 (3)	0.049 (4)	0.011 (2)	0.001 (3)	0.005 (3)
C5	0.034 (3)	0.042 (3)	0.039 (3)	0.009 (2)	0.005 (2)	0.003 (3)
C6	0.032 (3)	0.035 (3)	0.040 (3)	0.004 (2)	0.006 (2)	−0.002 (3)
C7	0.035 (3)	0.034 (3)	0.046 (4)	0.008 (2)	0.006 (2)	0.001 (2)
C8	0.031 (3)	0.060 (4)	0.072 (7)	0.000 (3)	0.020 (3)	0.001 (4)
C9	0.042 (3)	0.064 (4)	0.078 (5)	−0.008 (3)	0.019 (4)	−0.011 (4)
C10	0.045 (3)	0.052 (4)	0.056 (4)	−0.005 (3)	0.009 (3)	−0.017 (4)
C11	0.055 (4)	0.038 (3)	0.047 (4)	0.011 (3)	0.009 (3)	−0.008 (3)
C12	0.044 (3)	0.049 (3)	0.042 (3)	0.016 (3)	0.009 (3)	−0.001 (3)
C13	0.034 (3)	0.042 (3)	0.031 (3)	0.004 (2)	0.004 (2)	−0.001 (3)
C14	0.033 (3)	0.043 (3)	0.032 (3)	0.004 (2)	0.006 (2)	−0.004 (3)
C15	0.046 (3)	0.039 (3)	0.034 (3)	−0.003 (2)	−0.001 (3)	−0.001 (3)
C16	0.049 (3)	0.042 (3)	0.036 (3)	0.000 (2)	−0.002 (5)	0.002 (5)
C17	0.044 (3)	0.050 (4)	0.049 (4)	0.008 (3)	0.004 (3)	−0.008 (3)
C18	0.057 (4)	0.060 (4)	0.065 (5)	0.014 (3)	−0.004 (4)	0.008 (4)

Geometric parameters (Å, º)

Pd1—O1	2.003 (4)	C5—C6	1.426 (8)
Pd1—O3	2.005 (4)	C6—C7	1.400 (8)
Pd1—N1	1.991 (5)	C7—C8	1.413 (8)
Pd1—N2	1.994 (5)	C7—C12	1.424 (9)
O1—C13	1.281 (7)	C8—C9	1.36 (1)
O2—C13	1.218 (8)	C8—H8	0.930
O3—C15	1.295 (7)	C9—C10	1.38 (1)
O4—C15	1.255 (10)	C9—H9	0.930
O5A—H5AA	1.067	C10—H10	0.930
O5A—H5AB	1.058	C11—C12	1.366 (8)
O5B—H5BB	0.991	C11—H11	0.930
O5B—H5BA	0.924	C12—H12	0.930
N1—C1	1.330 (7)	C13—C14	1.548 (8)
N1—C5	1.358 (8)	C14—C15	1.528 (8)
N2—C6	1.350 (8)	C14—C16	1.56 (1)
N2—C10	1.329 (8)	C14—C17	1.548 (9)
C1—C2	1.38 (1)	C16—C18	1.519 (9)
C1—H1	0.930	C16—H16A	0.970
C2—C3	1.36 (1)	C16—H16B	0.970
C2—H2	0.930	C17—C18	1.54 (1)
C3—C4	1.415 (9)	C17—H17A	0.970
C3—H3	0.930	C17—H17B	0.970
C4—C5	1.392 (9)	C18—H18A	0.970
C4—C11	1.439 (9)	C18—H18B	0.970
Pd1···C11^i	3.515 (6)	O3···C7^i	3.421 (7)
Pd1···C12^i	3.549 (6)	O4···C2^iv	3.56 (1)
Pd1···C4^i	3.556 (6)	O4···C16^i	3.58 (1)
O1···C5^i	3.203 (7)	O4···C3^v	3.592 (10)
O1···C4^i	3.324 (7)	O5A···O5B^vi	2.99 (3)
O1···N1^i	3.338 (7)	O5A···O5B^vii	3.24 (5)
O1···C3^i	3.503 (8)	O5A···C2^iv	3.38 (2)
O1···C1^i	3.527 (9)	O5B···O5B^vi	2.53 (2)
O2···C8^ii	3.208 (10)	O5B···C9^viii	3.35 (1)
O2···C12^ii	3.243 (8)	O5B···C10^i	3.55 (1)
O2···C9^iii	3.463 (10)	N1···C11^i	3.417 (8)
O2···C16^i	3.48 (1)	N1···C13^vii	3.582 (8)
O2···C1^i	3.502 (8)	N2···C12^i	3.401 (8)
O3···C6^i	3.260 (7)	C16···C17^vii	3.44 (1)
O3···N2^i	3.399 (7)
O1—Pd1—O3	91.3 (2)	C8—C9—H9	119.4
O1—Pd1—N1	93.0 (2)	C10—C9—H9	119.4
O1—Pd1—N2	173.2 (2)	N2—C10—C9	121.4 (7)
O3—Pd1—N1	174.7 (2)	N2—C10—H10	119.3
O3—Pd1—N2	93.2 (2)	C9—C10—H10	119.3
N1—Pd1—N2	82.2 (2)	C4—C11—C12	121.1 (6)
Pd1—O1—C13	121.9 (4)	C4—C11—H11	119.5
Pd1—O3—C15	120.7 (4)	C12—C11—H11	119.4
H5AA—O5A—H5AB	112.3	C7—C12—C11	120.8 (6)
H5BB—O5B—H5BA	116.8	C7—C12—H12	119.6
Pd1—N1—C1	128.7 (5)	C11—C12—H12	119.6
Pd1—N1—C5	112.9 (4)	O1—C13—O2	122.7 (5)
C1—N1—C5	118.5 (5)	O1—C13—C14	116.8 (5)
Pd1—N2—C6	112.7 (4)	O2—C13—C14	120.4 (5)
Pd1—N2—C10	128.6 (5)	C13—C14—C15	111.2 (5)
C6—N2—C10	118.7 (5)	C13—C14—C16	109.6 (4)
N1—C1—C2	121.2 (6)	C13—C14—C17	114.7 (5)
N1—C1—H1	119.4	C15—C14—C16	114.8 (5)
C2—C1—H1	119.4	C15—C14—C17	116.2 (5)
C1—C2—C3	121.3 (6)	C16—C14—C17	88.4 (4)
C1—C2—H2	119.4	O3—C15—O4	121.9 (5)
C3—C2—H2	119.4	O3—C15—C14	117.9 (5)
C2—C3—C4	118.7 (6)	O4—C15—C14	120.2 (5)
C2—C3—H3	120.7	C14—C16—C18	89.4 (6)
C4—C3—H3	120.7	C14—C16—H16A	113.8
C3—C4—C5	116.7 (6)	C14—C16—H16B	113.7
C3—C4—C11	124.9 (6)	C18—C16—H16A	113.7
C5—C4—C11	118.4 (5)	C18—C16—H16B	113.7
N1—C5—C4	123.6 (5)	H16A—C16—H16B	111.0
N1—C5—C6	115.8 (5)	C14—C17—C18	89.1 (5)
C4—C5—C6	120.5 (5)	C14—C17—H17A	113.8
N2—C6—C5	116.4 (5)	C14—C17—H17B	113.8
N2—C6—C7	123.3 (5)	C18—C17—H17A	113.8
C5—C6—C7	120.3 (5)	C18—C17—H17B	113.8
C6—C7—C8	116.4 (5)	H17A—C17—H17B	111.0
C6—C7—C12	118.9 (5)	C16—C18—C17	90.2 (6)
C8—C7—C12	124.7 (6)	C16—C18—H18A	113.6
C7—C8—C9	119.0 (6)	C16—C18—H18B	113.6
C7—C8—H8	120.5	C17—C18—H18A	113.6
C9—C8—H8	120.5	C17—C18—H18B	113.6
C8—C9—C10	121.2 (6)	H18A—C18—H18B	110.9
Pd1—O1—C13—O2	−174.8 (5)	N2—Pd1—N1—C1	−178.9 (6)
Pd1—O1—C13—C14	6.9 (7)	N2—Pd1—N1—C5	0.8 (4)
Pd1—O3—C15—O4	175.7 (6)	N2—C6—C5—C4	178.8 (5)
Pd1—O3—C15—C14	−6.7 (7)	N2—C6—C7—C8	0.5 (9)
Pd1—N1—C1—C2	178.7 (5)	N2—C6—C7—C12	−179.3 (5)
Pd1—N1—C5—C4	−179.9 (5)	N2—C10—C9—C8	1 (1)
Pd1—N1—C5—C6	−0.2 (7)	C1—N1—C5—C4	−0.2 (9)
Pd1—N2—C6—C5	1.5 (6)	C1—N1—C5—C6	179.5 (6)
Pd1—N2—C6—C7	−179.4 (4)	C1—C2—C3—C4	1 (1)
Pd1—N2—C10—C9	178.4 (5)	C2—C1—N1—C5	−0.9 (9)
O1—Pd1—O3—C15	−33.3 (5)	C2—C3—C4—C5	−2.4 (9)
O1—Pd1—N1—C1	6.0 (6)	C2—C3—C4—C11	179.0 (7)
O1—Pd1—N1—C5	−174.3 (4)	C3—C4—C5—C6	−177.8 (6)
O1—C13—C14—C15	−60.0 (7)	C3—C4—C11—C12	177.7 (6)
O1—C13—C14—C16	68.1 (6)	C4—C5—C6—C7	−0.3 (9)
O1—C13—C14—C17	165.7 (5)	C4—C11—C12—C7	0.3 (10)
O2—C13—C14—C15	121.7 (7)	C5—C4—C11—C12	−0.9 (9)
O2—C13—C14—C16	−110.2 (7)	C5—C6—N2—C10	−179.3 (6)
O2—C13—C14—C17	−12.6 (8)	C5—C6—C7—C8	179.6 (6)
O3—Pd1—O1—C13	33.2 (5)	C5—C6—C7—C12	−0.2 (8)
O3—Pd1—N2—C6	176.1 (4)	C6—N2—C10—C9	−0.7 (10)
O3—Pd1—N2—C10	−3.0 (6)	C6—C5—C4—C11	0.9 (9)
O3—C15—C14—C13	59.9 (7)	C6—C7—C8—C9	0.1 (9)
O3—C15—C14—C16	−65.3 (7)	C6—C7—C12—C11	0.2 (9)
O3—C15—C14—C17	−166.5 (5)	C7—C6—N2—C10	−0.2 (9)
O4—C15—C14—C13	−122.4 (7)	C7—C8—C9—C10	0 (1)
O4—C15—C14—C16	112.4 (7)	C8—C7—C12—C11	−179.6 (6)
O4—C15—C14—C17	11.2 (9)	C9—C8—C7—C12	179.9 (6)
N1—Pd1—O1—C13	−149.9 (5)	C13—C14—C16—C18	103.0 (5)
N1—Pd1—N2—C6	−1.2 (4)	C13—C14—C17—C18	−98.4 (6)
N1—Pd1—N2—C10	179.7 (6)	C14—C16—C18—C17	12.8 (5)
N1—C1—C2—C3	0 (1)	C14—C17—C18—C16	−12.9 (5)
N1—C5—C4—C3	1.8 (9)	C15—C14—C16—C18	−131.0 (5)
N1—C5—C4—C11	−179.5 (6)	C15—C14—C17—C18	129.6 (5)
N1—C5—C6—N2	−0.8 (8)	C16—C14—C17—C18	12.5 (4)
N1—C5—C6—C7	180.0 (5)	C17—C14—C16—C18	−12.7 (5)
N2—Pd1—O3—C15	151.8 (5)	C17—C14—C16—C18	−12.7 (5)

Symmetry codes: (i) x, y, z+1; (ii) x−1/2, −y+1/2, z+3/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1/2, y+1/2, z+1/2; (v) −x+1/2, y+1/2, z+3/2; (vi) −x+1, −y+1, z; (vii) x, y, z−1; (viii) −x+1, −y+1, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5A—H5AA···O4	1.07	2.11	3.17 (2)	177
O5B—H5BA···O4	0.92	1.83	2.753 (12)	179
O5A—H5AB···O5B^vii	1.06	2.18	3.24 (4)	179
O5B—H5BB···O5A^vi	0.99	1.99	2.99 (3)	179

Symmetry codes: (vi) −x+1, −y+1, z; (vii) x, y, z−1.

(IIb) (1,1-cyclobutanedicarboxylato-κ²O,O') (1,10-phenanthroline-κ²N,N')palladium(II) dihydrate

Crystal data

[Pd(C6H6O4)(C12H8N2)]·2H2O	Z = 4
Mr = 464.76	F(000) = 936.0
Triclinic, P1	Dx = 1.740 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 11.079 (2) Å	Cell parameters from 25 reflections
b = 11.826 (3) Å	θ = 14.3–15.0°
c = 13.678 (4) Å	µ = 1.09 mm^−1
α = 85.50 (2)°	T = 296 K
β = 84.55 (2)°	Plate, pale yellow
γ = 85.87 (2)°	0.20 × 0.20 × 0.10 mm
V = 1774.7 (8) Å^3

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.033
ω/2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −14→14
Tmin = 0.777, Tmax = 0.897	k = −15→0
8545 measured reflections	l = −17→17
8164 independent reflections	3 standard reflections every 150 reflections
5125 reflections with I > 2σ(I)	intensity decay: 2.1%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0563P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.118	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.44 e Å^−3
8164 reflections	Δρmin = −0.79 e Å^−3
487 parameters

Special details

Refinement. Refinement using reflections with F² > −10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Pd1	0.04535 (3)	0.85131 (3)	0.36336 (2)	0.0395 (1)
Pd2	0.34336 (3)	0.35543 (3)	0.05109 (2)	0.0408 (1)
O1	−0.1010 (3)	0.7652 (3)	0.3516 (2)	0.0511 (8)
O2	−0.1815 (3)	0.6119 (3)	0.3141 (3)	0.067 (1)
O3	0.1535 (3)	0.7106 (3)	0.3728 (3)	0.0503 (8)
O4	0.1748 (3)	0.5257 (3)	0.3620 (3)	0.067 (1)
O5	0.3002 (3)	0.2596 (3)	−0.0527 (2)	0.0524 (8)
O6	0.2367 (4)	0.0972 (4)	−0.0899 (3)	0.077 (1)
O7	0.3823 (3)	0.2200 (3)	0.1418 (2)	0.0538 (8)
O8	0.3703 (4)	0.0364 (3)	0.1744 (3)	0.070 (1)
O9	0.6031 (4)	0.9823 (5)	0.2395 (3)	0.109 (2)
O10	0.3868 (4)	0.2139 (4)	0.6254 (4)	0.095 (1)
O11	0.5400 (4)	0.2996 (4)	0.4579 (4)	0.090 (1)
O12	0.6941 (4)	0.4773 (4)	0.4684 (3)	0.087 (1)
N1	−0.0506 (3)	1.0013 (3)	0.3657 (3)	0.0414 (8)
N2	0.1821 (3)	0.9481 (3)	0.3820 (3)	0.0428 (8)
N3	0.3197 (3)	0.4993 (3)	−0.0341 (3)	0.0454 (9)
N4	0.3893 (3)	0.4640 (3)	0.1449 (3)	0.0444 (9)
C1	−0.1683 (5)	1.0236 (5)	0.3598 (3)	0.052 (1)
C2	−0.2233 (5)	1.1334 (5)	0.3698 (4)	0.058 (1)
C3	−0.1551 (5)	1.2198 (5)	0.3854 (4)	0.060 (1)
C4	−0.0290 (5)	1.2007 (4)	0.3885 (3)	0.050 (1)
C5	0.0184 (4)	1.0881 (4)	0.3798 (3)	0.0417 (10)
C6	0.1446 (4)	1.0595 (4)	0.3874 (3)	0.0409 (9)
C7	0.2966 (4)	0.9163 (4)	0.3923 (4)	0.051 (1)
C8	0.3794 (5)	0.9944 (5)	0.4081 (4)	0.059 (1)
C9	0.3451 (5)	1.1066 (5)	0.4110 (4)	0.060 (1)
C10	0.2232 (5)	1.1429 (4)	0.4017 (4)	0.051 (1)
C11	0.1737 (6)	1.2568 (4)	0.4072 (4)	0.060 (1)
C12	0.0541 (6)	1.2852 (4)	0.4016 (4)	0.060 (1)
C13	−0.0926 (4)	0.6677 (4)	0.3125 (3)	0.046 (1)
C14	0.1258 (4)	0.6183 (4)	0.3380 (4)	0.046 (1)
C15	0.0301 (4)	0.6291 (4)	0.2635 (3)	0.044 (1)
C16	0.0600 (4)	0.7053 (4)	0.1665 (4)	0.052 (1)
C17	0.0205 (5)	0.6099 (5)	0.1085 (4)	0.068 (2)
C18	0.0290 (5)	0.5278 (5)	0.2004 (4)	0.062 (1)
C21	0.2856 (4)	0.5111 (5)	−0.1248 (4)	0.058 (1)
C22	0.2755 (6)	0.6187 (6)	−0.1757 (5)	0.076 (2)
C23	0.2995 (5)	0.7142 (6)	−0.1312 (5)	0.075 (2)
C24	0.3357 (4)	0.7033 (5)	−0.0356 (5)	0.061 (1)
C25	0.3435 (4)	0.5931 (4)	0.0098 (4)	0.046 (1)
C26	0.3819 (4)	0.5737 (4)	0.1066 (4)	0.046 (1)
C27	0.4249 (4)	0.4414 (5)	0.2341 (4)	0.055 (1)
C28	0.4568 (5)	0.5273 (6)	0.2902 (4)	0.071 (2)
C29	0.4512 (5)	0.6370 (5)	0.2524 (5)	0.071 (2)
C30	0.4125 (5)	0.6634 (5)	0.1580 (4)	0.059 (1)
C31	0.4022 (5)	0.7762 (5)	0.1099 (5)	0.073 (2)
C32	0.3648 (5)	0.7946 (5)	0.0190 (5)	0.073 (2)
C33	0.2530 (4)	0.1631 (4)	−0.0300 (4)	0.051 (1)
C34	0.3308 (5)	0.1264 (4)	0.1355 (4)	0.050 (1)
C35	0.2166 (4)	0.1338 (4)	0.0802 (3)	0.047 (1)
C36	0.1091 (4)	0.2131 (4)	0.1203 (4)	0.052 (1)
C37	0.0239 (5)	0.1207 (5)	0.1066 (5)	0.072 (2)
C38	0.1333 (5)	0.0340 (5)	0.0995 (5)	0.066 (1)
H1	−0.2160	0.9652	0.3486	0.0630*
H2	−0.3065	1.1468	0.3658	0.0699*
H3	−0.1919	1.2919	0.3941	0.0719*
H7	0.3227	0.8401	0.3888	0.0609*
H8	0.4595	0.9694	0.4168	0.0712*
H9	0.4016	1.1587	0.4191	0.0724*
H9A	0.6578	0.9540	0.1890	0.1307*
H9B	0.5267	0.9980	0.2197	0.1307*
H10A	0.3269	0.2579	0.6312	0.1142*
H10B	0.3904	0.1519	0.6636	0.1142*
H11	0.2252	1.3135	0.4148	0.0721*
H11A	0.4958	0.2784	0.5055	0.1071*
H11B	0.5803	0.3522	0.4633	0.1071*
H12	0.0250	1.3605	0.4064	0.0726*
H12A	0.7380	0.4990	0.4212	0.1032*
H12B	0.7453	0.4699	0.5066	0.1032*
H16A	0.0089	0.7753	0.1611	0.0626*
H16B	0.1453	0.7199	0.1534	0.0626*
H17A	−0.0611	0.6233	0.0881	0.0814*
H17B	0.0781	0.5901	0.0536	0.0814*
H18A	0.1034	0.4791	0.1991	0.0745*
H18B	−0.0416	0.4836	0.2161	0.0745*
H21	0.2681	0.4472	−0.1551	0.0697*
H22	0.2525	0.6255	−0.2396	0.0908*
H23	0.2916	0.7856	−0.1646	0.0902*
H27	0.4289	0.3665	0.2606	0.0659*
H28	0.4817	0.5092	0.3529	0.0853*
H29	0.4728	0.6944	0.2889	0.0849*
H31	0.4220	0.8375	0.1425	0.0875*
H32	0.3575	0.8686	−0.0092	0.0874*
H36A	0.1123	0.2293	0.1884	0.0618*
H36B	0.0953	0.2824	0.0789	0.0618*
H37A	−0.0170	0.1331	0.0467	0.0868*
H37B	−0.0337	0.1054	0.1633	0.0868*
H38A	0.1352	−0.0135	0.0446	0.0794*
H38B	0.1449	−0.0115	0.1604	0.0794*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0415 (2)	0.0334 (2)	0.0452 (2)	−0.0063 (1)	−0.0090 (2)	−0.0022 (1)
Pd2	0.0435 (2)	0.0379 (2)	0.0422 (2)	−0.0088 (1)	−0.0056 (2)	−0.0034 (2)
O1	0.038 (2)	0.060 (2)	0.058 (2)	−0.009 (1)	−0.007 (1)	−0.008 (2)
O2	0.055 (2)	0.080 (3)	0.071 (3)	−0.035 (2)	0.000 (2)	−0.011 (2)
O3	0.051 (2)	0.035 (2)	0.068 (2)	−0.002 (1)	−0.021 (2)	−0.005 (2)
O4	0.077 (3)	0.032 (2)	0.098 (3)	−0.004 (2)	−0.043 (2)	0.001 (2)
O5	0.062 (2)	0.057 (2)	0.040 (2)	−0.016 (2)	−0.003 (1)	−0.009 (2)
O6	0.097 (3)	0.078 (3)	0.063 (2)	−0.033 (2)	0.005 (2)	−0.034 (2)
O7	0.066 (2)	0.042 (2)	0.057 (2)	−0.012 (2)	−0.022 (2)	0.000 (2)
O8	0.080 (3)	0.042 (2)	0.092 (3)	0.000 (2)	−0.034 (2)	0.002 (2)
O9	0.068 (3)	0.189 (6)	0.075 (3)	0.013 (3)	−0.016 (2)	−0.047 (3)
O10	0.070 (3)	0.099 (4)	0.121 (4)	−0.004 (3)	−0.008 (3)	−0.032 (3)
O11	0.083 (3)	0.087 (3)	0.103 (4)	−0.031 (2)	0.001 (3)	−0.019 (3)
O12	0.084 (3)	0.105 (3)	0.076 (3)	−0.048 (3)	−0.026 (2)	0.026 (2)
N1	0.049 (2)	0.038 (2)	0.038 (2)	−0.005 (2)	−0.008 (2)	0.001 (2)
N2	0.045 (2)	0.038 (2)	0.047 (2)	−0.007 (2)	−0.009 (2)	−0.005 (2)
N3	0.039 (2)	0.044 (2)	0.054 (2)	−0.010 (2)	−0.003 (2)	0.004 (2)
N4	0.041 (2)	0.044 (2)	0.050 (2)	−0.008 (2)	−0.005 (2)	−0.009 (2)
C1	0.054 (3)	0.058 (3)	0.045 (3)	−0.001 (2)	−0.006 (2)	−0.002 (2)
C2	0.055 (3)	0.064 (3)	0.053 (3)	0.012 (3)	−0.008 (2)	0.002 (3)
C3	0.081 (4)	0.048 (3)	0.048 (3)	0.016 (3)	−0.009 (3)	−0.004 (2)
C4	0.075 (3)	0.036 (2)	0.037 (2)	0.002 (2)	−0.007 (2)	−0.001 (2)
C5	0.055 (3)	0.035 (2)	0.035 (2)	−0.002 (2)	−0.008 (2)	0.003 (2)
C6	0.054 (3)	0.036 (2)	0.033 (2)	−0.009 (2)	−0.005 (2)	0.000 (2)
C7	0.047 (3)	0.052 (3)	0.055 (3)	−0.002 (2)	−0.010 (2)	−0.006 (2)
C8	0.047 (3)	0.075 (4)	0.060 (3)	−0.013 (3)	−0.012 (2)	−0.008 (3)
C9	0.064 (3)	0.065 (3)	0.057 (3)	−0.030 (3)	−0.008 (3)	−0.004 (3)
C10	0.068 (3)	0.043 (3)	0.046 (3)	−0.015 (2)	−0.010 (2)	−0.003 (2)
C11	0.087 (4)	0.042 (3)	0.055 (3)	−0.022 (3)	−0.013 (3)	−0.005 (2)
C12	0.096 (4)	0.032 (2)	0.053 (3)	−0.007 (3)	−0.007 (3)	−0.002 (2)
C13	0.043 (2)	0.049 (3)	0.046 (3)	−0.015 (2)	−0.010 (2)	0.003 (2)
C14	0.046 (2)	0.036 (2)	0.058 (3)	−0.011 (2)	−0.011 (2)	0.002 (2)
C15	0.048 (2)	0.038 (2)	0.048 (3)	−0.009 (2)	−0.011 (2)	0.000 (2)
C16	0.045 (3)	0.055 (3)	0.056 (3)	−0.009 (2)	−0.003 (2)	0.001 (2)
C17	0.056 (3)	0.087 (4)	0.063 (4)	−0.010 (3)	−0.001 (3)	−0.023 (3)
C18	0.061 (3)	0.056 (3)	0.075 (4)	−0.009 (3)	−0.017 (3)	−0.019 (3)
C21	0.050 (3)	0.066 (3)	0.060 (3)	−0.014 (2)	−0.014 (2)	0.005 (3)
C22	0.077 (4)	0.082 (4)	0.066 (4)	−0.009 (3)	−0.024 (3)	0.026 (3)
C23	0.061 (3)	0.071 (4)	0.089 (5)	−0.004 (3)	−0.012 (3)	0.032 (4)
C24	0.043 (3)	0.048 (3)	0.088 (4)	−0.006 (2)	0.002 (3)	0.010 (3)
C25	0.035 (2)	0.043 (3)	0.059 (3)	−0.005 (2)	0.001 (2)	0.001 (2)
C26	0.039 (2)	0.046 (3)	0.055 (3)	−0.007 (2)	−0.001 (2)	−0.011 (2)
C27	0.053 (3)	0.065 (3)	0.048 (3)	−0.009 (2)	−0.009 (2)	−0.003 (2)
C28	0.070 (4)	0.093 (5)	0.056 (3)	−0.015 (3)	−0.014 (3)	−0.025 (3)
C29	0.063 (3)	0.071 (4)	0.085 (4)	−0.012 (3)	−0.008 (3)	−0.037 (3)
C30	0.047 (3)	0.056 (3)	0.077 (4)	−0.014 (2)	0.006 (3)	−0.025 (3)
C31	0.059 (3)	0.045 (3)	0.115 (5)	−0.012 (3)	0.007 (3)	−0.022 (3)
C32	0.063 (4)	0.039 (3)	0.113 (5)	−0.005 (2)	0.008 (3)	0.002 (3)
C33	0.046 (3)	0.056 (3)	0.055 (3)	−0.007 (2)	−0.001 (2)	−0.020 (2)
C34	0.061 (3)	0.040 (3)	0.050 (3)	−0.004 (2)	−0.009 (2)	−0.006 (2)
C35	0.057 (3)	0.037 (2)	0.047 (3)	−0.012 (2)	−0.004 (2)	−0.003 (2)
C36	0.050 (3)	0.062 (3)	0.043 (3)	−0.006 (2)	−0.004 (2)	−0.003 (2)
C37	0.062 (3)	0.091 (5)	0.066 (4)	−0.028 (3)	−0.007 (3)	0.007 (3)
C38	0.083 (4)	0.050 (3)	0.069 (4)	−0.025 (3)	−0.007 (3)	−0.002 (3)

Geometric parameters (Å, º)

Pd1—O1	2.001 (3)	C10—C11	1.423 (7)
Pd1—O3	1.982 (3)	C11—C12	1.350 (9)
Pd1—N1	2.002 (4)	C11—H11	0.930
Pd1—N2	2.010 (4)	C12—H12	0.930
Pd2—O5	1.997 (4)	C13—C15	1.513 (6)
Pd2—O7	1.995 (3)	C14—C15	1.530 (7)
Pd2—N3	2.001 (4)	C15—C16	1.566 (6)
Pd2—N4	2.007 (4)	C15—C18	1.532 (7)
O1—C13	1.302 (6)	C16—C17	1.541 (8)
O2—C13	1.223 (6)	C16—H16A	0.970
O3—C14	1.293 (6)	C16—H16B	0.970
O4—C14	1.222 (5)	C17—C18	1.532 (8)
O5—C33	1.293 (6)	C17—H17A	0.970
O6—C33	1.208 (7)	C17—H17B	0.970
O7—C34	1.294 (6)	C18—H18A	0.970
O8—C34	1.223 (6)	C18—H18B	0.970
O9—H9A	0.940	C21—C22	1.404 (8)
O9—H9B	0.915	C21—H21	0.930
O10—H10A	0.815	C22—C23	1.378 (10)
O10—H10B	0.867	C22—H22	0.930
O11—H11A	0.811	C23—C24	1.398 (9)
O11—H11B	0.803	C23—H23	0.930
O12—H12A	0.807	C24—C25	1.399 (7)
O12—H12B	0.803	C24—C32	1.431 (9)
N1—C1	1.320 (6)	C25—C26	1.425 (7)
N1—C5	1.359 (6)	C26—C30	1.396 (8)
N2—C6	1.357 (6)	C27—C28	1.404 (9)
N2—C7	1.314 (6)	C27—H27	0.930
N3—C21	1.325 (7)	C28—C29	1.357 (9)
N3—C25	1.355 (6)	C28—H28	0.930
N4—C26	1.361 (6)	C29—C30	1.404 (9)
N4—C27	1.320 (6)	C29—H29	0.930
C1—C2	1.405 (8)	C30—C31	1.442 (8)
C1—H1	0.930	C31—C32	1.35 (1)
C2—C3	1.356 (8)	C31—H31	0.930
C2—H2	0.930	C32—H32	0.930
C3—C4	1.403 (8)	C33—C35	1.541 (7)
C3—H3	0.930	C34—C35	1.529 (7)
C4—C5	1.406 (6)	C35—C36	1.547 (6)
C4—C12	1.439 (8)	C35—C38	1.541 (7)
C5—C6	1.426 (6)	C36—C37	1.528 (8)
C6—C10	1.399 (7)	C36—H36A	0.970
C7—C8	1.391 (8)	C36—H36B	0.970
C7—H7	0.930	C37—C38	1.531 (8)
C8—C9	1.356 (8)	C37—H37A	0.970
C8—H8	0.930	C37—H37B	0.970
C9—C10	1.401 (7)	C38—H38A	0.970
C9—H9	0.930	C38—H38B	0.970
Pd1···C4^i	3.392 (4)	O8···N2^vii	3.496 (5)
Pd1···C12^i	3.595 (5)	O9···O10^vi	2.853 (7)
Pd2···C24^ii	3.562 (5)	O9···C1^viii	3.233 (7)
Pd2···C25^ii	3.574 (4)	O9···C2^viii	3.423 (8)
O1···O10^iii	3.146 (5)	O10···C29^vi	3.258 (8)
O1···C11^i	3.316 (6)	O10···C9^vii	3.368 (8)
O1···C12^i	3.463 (6)	O10···C8^vi	3.466 (7)
O2···O12^iv	2.850 (6)	O10···C13^iii	3.509 (6)
O2···O10^iii	3.056 (6)	O11···C2^ix	3.350 (7)
O2···C21^v	3.398 (7)	O11···C9^vii	3.390 (8)
O3···O12^vi	3.451 (5)	O11···C3^ix	3.513 (7)
O3···C3^i	3.472 (6)	O12···C14^vi	3.533 (7)
O4···O12^vi	2.848 (6)	O12···C28^vi	3.555 (7)
O4···C11^vii	3.192 (6)	O12···C3^ix	3.578 (7)
O4···C12^vii	3.216 (6)	N1···C6^i	3.474 (5)
O5···C31^ii	3.320 (7)	N2···C2^i	3.518 (6)
O5···C30^ii	3.518 (6)	N2···C1^i	3.562 (6)
O6···O9^ii	2.756 (6)	N3···C26^ii	3.429 (6)
O7···C32^ii	3.397 (7)	N3···N4^ii	3.471 (5)
O7···C24^ii	3.468 (6)	N4···C25^ii	3.526 (6)
O8···O9^vii	2.822 (6)	C1···C6^i	3.549 (6)
O8···C8^vii	3.206 (7)	C2···C7^i	3.296 (7)
O8···C31^vii	3.253 (7)	C21···C27^ii	3.473 (7)
O8···C7^vii	3.256 (6)	C21···C28^ii	3.496 (7)
O8···C9^vii	3.385 (7)	C22···C27^ii	3.378 (8)
O1—Pd1—O3	92.8 (1)	C15—C16—H16B	113.9
O1—Pd1—N1	93.3 (1)	C17—C16—H16A	113.9
O1—Pd1—N2	174.7 (1)	C17—C16—H16B	113.9
O3—Pd1—N1	172.7 (2)	H16A—C16—H16B	111.1
O3—Pd1—N2	91.6 (1)	C16—C17—C18	89.3 (4)
N1—Pd1—N2	82.1 (1)	C16—C17—H17A	113.8
O5—Pd2—O7	92.6 (1)	C16—C17—H17B	113.8
O5—Pd2—N3	92.7 (2)	C18—C17—H17A	113.8
O5—Pd2—N4	174.4 (1)	C18—C17—H17B	113.8
O7—Pd2—N3	173.5 (2)	H17A—C17—H17B	111.0
O7—Pd2—N4	92.7 (1)	C15—C18—C17	89.8 (4)
N3—Pd2—N4	82.0 (2)	C15—C18—H18A	113.7
Pd1—O1—C13	121.8 (3)	C15—C18—H18B	113.7
Pd1—O3—C14	121.1 (3)	C17—C18—H18A	113.7
Pd2—O5—C33	121.3 (3)	C17—C18—H18B	113.7
Pd2—O7—C34	119.8 (3)	H18A—C18—H18B	110.9
H9A—O9—H9B	112.0	N3—C21—C22	120.8 (5)
H10A—O10—H10B	119.2	N3—C21—H21	119.6
H11A—O11—H11B	117.7	C22—C21—H21	119.6
H12A—O12—H12B	96.4	C21—C22—C23	120.3 (6)
Pd1—N1—C1	128.9 (3)	C21—C22—H22	119.9
Pd1—N1—C5	112.6 (3)	C23—C22—H22	119.9
C1—N1—C5	118.5 (4)	C22—C23—C24	119.6 (6)
Pd1—N2—C6	112.4 (3)	C22—C23—H23	120.2
Pd1—N2—C7	128.5 (3)	C24—C23—H23	120.2
C6—N2—C7	119.0 (4)	C23—C24—C25	116.4 (5)
Pd2—N3—C21	127.8 (4)	C23—C24—C32	125.7 (5)
Pd2—N3—C25	113.1 (3)	C25—C24—C32	117.9 (5)
C21—N3—C25	119.1 (4)	N3—C25—C24	123.8 (5)
Pd2—N4—C26	112.3 (3)	N3—C25—C26	115.9 (4)
Pd2—N4—C27	128.6 (3)	C24—C25—C26	120.3 (5)
C26—N4—C27	119.1 (4)	N4—C26—C25	116.8 (4)
N1—C1—C2	121.7 (5)	N4—C26—C30	122.2 (5)
N1—C1—H1	119.2	C25—C26—C30	121.1 (4)
C2—C1—H1	119.2	N4—C27—C28	121.8 (5)
C1—C2—C3	120.0 (5)	N4—C27—H27	119.1
C1—C2—H2	120.0	C28—C27—H27	119.1
C3—C2—H2	120.0	C27—C28—C29	119.7 (6)
C2—C3—C4	120.1 (5)	C27—C28—H28	120.2
C2—C3—H3	119.9	C29—C28—H28	120.2
C4—C3—H3	119.9	C28—C29—C30	119.6 (6)
C3—C4—C5	116.2 (5)	C28—C29—H29	120.2
C3—C4—C12	125.8 (4)	C30—C29—H29	120.2
C5—C4—C12	118.0 (5)	C26—C30—C29	117.6 (5)
N1—C5—C4	123.4 (4)	C26—C30—C31	117.4 (5)
N1—C5—C6	116.4 (4)	C29—C30—C31	124.9 (6)
C4—C5—C6	120.2 (4)	C30—C31—C32	121.4 (6)
N2—C6—C5	116.5 (4)	C30—C31—H31	119.3
N2—C6—C10	122.8 (4)	C32—C31—H31	119.3
C5—C6—C10	120.7 (4)	C24—C32—C31	121.8 (5)
N2—C7—C8	121.3 (5)	C24—C32—H32	119.1
N2—C7—H7	119.4	C31—C32—H32	119.1
C8—C7—H7	119.4	O5—C33—O6	123.5 (5)
C7—C8—C9	120.9 (5)	O5—C33—C35	116.5 (4)
C7—C8—H8	119.6	O6—C33—C35	119.9 (4)
C9—C8—H8	119.6	O7—C34—O8	121.2 (5)
C8—C9—C10	119.1 (5)	O7—C34—C35	117.2 (4)
C8—C9—H9	120.4	O8—C34—C35	121.6 (5)
C10—C9—H9	120.4	C33—C35—C34	108.6 (4)
C6—C10—C9	116.9 (4)	C33—C35—C36	111.9 (4)
C6—C10—C11	118.0 (5)	C33—C35—C38	113.5 (4)
C9—C10—C11	125.1 (5)	C34—C35—C36	116.3 (4)
C10—C11—C12	122.1 (5)	C34—C35—C38	117.0 (4)
C10—C11—H11	119.0	C36—C35—C38	88.4 (4)
C12—C11—H11	119.0	C35—C36—C37	88.5 (4)
C4—C12—C11	121.0 (5)	C35—C36—H36A	113.9
C4—C12—H12	119.5	C35—C36—H36B	113.9
C11—C12—H12	119.5	C37—C36—H36A	113.9
O1—C13—O2	120.6 (4)	C37—C36—H36B	113.9
O1—C13—C15	117.2 (4)	H36A—C36—H36B	111.1
O2—C13—C15	122.2 (4)	C36—C37—C38	89.5 (4)
O3—C14—O4	121.8 (5)	C36—C37—H37A	113.7
O3—C14—C15	117.4 (4)	C36—C37—H37B	113.7
O4—C14—C15	120.8 (4)	C38—C37—H37A	113.7
C13—C15—C14	110.3 (4)	C38—C37—H37B	113.7
C13—C15—C16	110.1 (4)	H37A—C37—H37B	111.0
C13—C15—C18	114.9 (4)	C35—C38—C37	88.6 (4)
C14—C15—C16	116.4 (4)	C35—C38—H38A	113.9
C14—C15—C18	115.4 (4)	C35—C38—H38B	113.9
C16—C15—C18	88.3 (4)	C37—C38—H38A	113.9
C15—C16—C17	88.3 (4)	C37—C38—H38B	113.9
C15—C16—H16A	113.9	H38A—C38—H38B	111.1
Pd1—O1—C13—O2	173.4 (3)	N3—C21—C22—C23	−0.9 (8)
Pd1—O1—C13—C15	−8.2 (5)	N3—C25—C24—C23	0.8 (7)
Pd1—O3—C14—O4	−163.0 (3)	N3—C25—C24—C32	−179.3 (4)
Pd1—O3—C14—C15	18.1 (5)	N3—C25—C26—N4	−0.7 (6)
Pd1—N1—C1—C2	175.2 (3)	N3—C25—C26—C30	178.1 (4)
Pd1—N1—C5—C4	−177.2 (3)	N4—Pd2—O7—C34	155.6 (3)
Pd1—N1—C5—C6	1.8 (5)	N4—Pd2—N3—C21	179.1 (4)
Pd1—N2—C6—C5	0.4 (5)	N4—Pd2—N3—C25	−0.4 (3)
Pd1—N2—C6—C10	179.0 (3)	N4—C26—C25—C24	−178.8 (4)
Pd1—N2—C7—C8	−177.7 (4)	N4—C26—C30—C29	−0.4 (7)
Pd2—O5—C33—O6	−172.4 (4)	N4—C26—C30—C31	179.5 (4)
Pd2—O5—C33—C35	7.8 (5)	N4—C27—C28—C29	0.1 (8)
Pd2—O7—C34—O8	164.5 (4)	C1—N1—C5—C4	0.0 (6)
Pd2—O7—C34—C35	−17.4 (5)	C1—N1—C5—C6	179.0 (4)
Pd2—N3—C21—C22	−178.7 (4)	C1—C2—C3—C4	2.0 (7)
Pd2—N3—C25—C24	178.8 (4)	C2—C1—N1—C5	−1.4 (6)
Pd2—N3—C25—C26	0.7 (5)	C2—C3—C4—C5	−3.2 (7)
Pd2—N4—C26—C25	0.3 (5)	C2—C3—C4—C12	178.2 (5)
Pd2—N4—C26—C30	−178.5 (4)	C3—C4—C5—C6	−176.6 (4)
Pd2—N4—C27—C28	178.5 (4)	C3—C4—C12—C11	177.5 (5)
O1—Pd1—O3—C14	23.4 (3)	C4—C5—C6—C10	−1.2 (6)
O1—Pd1—N1—C1	−0.7 (4)	C4—C12—C11—C10	−0.9 (8)
O1—Pd1—N1—C5	176.1 (3)	C5—C4—C12—C11	−1.1 (7)
O1—C13—C15—C14	60.0 (5)	C5—C6—N2—C7	−177.5 (4)
O1—C13—C15—C16	−69.8 (5)	C5—C6—C10—C9	178.3 (4)
O1—C13—C15—C18	−167.6 (4)	C5—C6—C10—C11	−0.8 (7)
O2—C13—C15—C14	−121.7 (5)	C6—N2—C7—C8	−0.2 (7)
O2—C13—C15—C16	108.5 (5)	C6—C5—C4—C12	2.1 (6)
O2—C13—C15—C18	10.8 (6)	C6—C10—C9—C8	−1.5 (7)
O3—Pd1—O1—C13	−29.0 (3)	C6—C10—C11—C12	1.8 (7)
O3—Pd1—N2—C6	−175.7 (3)	C7—N2—C6—C10	1.1 (6)
O3—Pd1—N2—C7	2.0 (4)	C7—C8—C9—C10	2.5 (8)
O3—C14—C15—C13	−66.6 (5)	C8—C9—C10—C11	177.5 (5)
O3—C14—C15—C16	59.7 (5)	C9—C10—C11—C12	−177.2 (5)
O3—C14—C15—C18	161.2 (4)	C13—C15—C16—C17	−100.4 (4)
O4—C14—C15—C13	114.5 (5)	C13—C15—C18—C17	95.8 (4)
O4—C14—C15—C16	−119.2 (5)	C14—C15—C16—C17	133.2 (4)
O4—C14—C15—C18	−17.7 (6)	C14—C15—C18—C17	−134.2 (4)
O5—Pd2—O7—C34	−26.5 (3)	C15—C16—C17—C18	−15.6 (4)
O5—Pd2—N3—C21	0.8 (4)	C15—C18—C17—C16	15.9 (4)
O5—Pd2—N3—C25	−178.7 (3)	C16—C15—C18—C17	−15.7 (4)
O5—C33—C35—C34	−62.3 (5)	C17—C16—C15—C18	15.6 (4)
O5—C33—C35—C36	67.5 (5)	C21—N3—C25—C24	−0.8 (6)
O5—C33—C35—C38	165.7 (4)	C21—N3—C25—C26	−178.9 (4)
O6—C33—C35—C34	117.8 (5)	C21—C22—C23—C24	0.9 (8)
O6—C33—C35—C36	−112.4 (5)	C22—C21—N3—C25	0.8 (7)
O6—C33—C35—C38	−14.2 (6)	C22—C23—C24—C25	−0.9 (8)
O7—Pd2—O5—C33	31.8 (3)	C22—C23—C24—C32	179.3 (5)
O7—Pd2—N4—C26	176.4 (3)	C23—C24—C25—C26	178.9 (4)
O7—Pd2—N4—C27	−3.0 (4)	C23—C24—C32—C31	−178.1 (5)
O7—C34—C35—C33	68.6 (5)	C24—C25—C26—C30	−0.1 (7)
O7—C34—C35—C36	−58.7 (6)	C24—C32—C31—C30	−1.4 (9)
O7—C34—C35—C38	−161.2 (4)	C25—C24—C32—C31	2.1 (8)
O8—C34—C35—C33	−113.3 (5)	C25—C26—N4—C27	179.7 (4)
O8—C34—C35—C36	119.4 (5)	C25—C26—C30—C29	−179.1 (4)
O8—C34—C35—C38	16.8 (7)	C25—C26—C30—C31	0.8 (7)
N1—Pd1—O1—C13	155.1 (3)	C26—N4—C27—C28	−0.8 (7)
N1—Pd1—N2—C6	0.4 (3)	C26—C25—C24—C32	−1.3 (7)
N1—Pd1—N2—C7	178.1 (4)	C26—C30—C29—C28	−0.4 (8)
N1—C1—C2—C3	0.4 (7)	C26—C30—C31—C32	0.0 (8)
N1—C5—C4—C3	2.3 (6)	C27—N4—C26—C30	1.0 (6)
N1—C5—C4—C12	−179.0 (4)	C27—C28—C29—C30	0.5 (8)
N1—C5—C6—N2	−1.5 (6)	C28—C29—C30—C31	179.8 (5)
N1—C5—C6—C10	179.8 (4)	C29—C30—C31—C32	179.8 (5)
N2—Pd1—O3—C14	−159.5 (3)	C33—C35—C36—C37	98.0 (4)
N2—Pd1—N1—C1	−178.0 (4)	C33—C35—C38—C37	−96.5 (5)
N2—Pd1—N1—C5	−1.2 (3)	C34—C35—C36—C37	−136.4 (4)
N2—C6—C5—C4	177.5 (4)	C34—C35—C38—C37	135.7 (4)
N2—C6—C10—C9	−0.3 (7)	C35—C36—C37—C38	16.9 (4)
N2—C6—C10—C11	−179.4 (4)	C35—C38—C37—C36	−16.9 (4)
N2—C7—C8—C9	−1.7 (8)	C36—C35—C38—C37	16.7 (4)
N3—Pd2—O5—C33	−152.0 (3)	C37—C36—C35—C38	−16.8 (4)
N3—Pd2—N4—C26	0.1 (3)	C37—C36—C35—C38	−16.8 (4)
N3—Pd2—N4—C27	−179.3 (4)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z+1; (iv) x−1, y, z; (v) −x, −y+1, −z; (vi) −x+1, −y+1, −z+1; (vii) x, y−1, z; (viii) x+1, y, z; (ix) x+1, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O6^ii	0.94	1.82	2.756 (6)	179
O9—H9B···O8^x	0.92	1.91	2.822 (6)	177
O10—H10A···O2^iii	0.82	2.26	3.056 (6)	165
O10—H10B···O9^vi	0.87	1.99	2.853 (8)	175
O11—H11A···O10	0.81	2.07	2.881 (7)	176
O11—H11B···O12	0.80	2.02	2.822 (6)	175
O12—H12A···O2^viii	0.81	2.08	2.850 (5)	159
O12—H12B···O4^vi	0.80	2.08	2.848 (5)	159

Symmetry codes: (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (viii) x+1, y, z; (x) x, y+1, z.