Di-μ-acetato-κ4O:O′-bis­{[2-(2-pyrid­yl)phenyl-κ2C,N]palladium(II)}

Dinçer, M.; Özdemir, N.; Günay, M.E.; Çetinkaya, B.

doi:10.1107/S1600536808001736

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m381

doi:10.1107/S1600536808001736

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Di-μ-acetato-κ⁴O:O′-bis{[2-(2-pyridyl)phenyl-κ²C,N]palladium(II)}

Muharrem Dinçer,^a Namık Özdemir,^a M. Emin Günay ^b and Bekir Çetinkaya ^c ^*

^aOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, ^bAdnan Menderes University, Arts and Sciences Faculty, Department of Chemistry, 09010 Aydın, Turkey, and ^cEge University, Science Faculty, Department of Chemistry, 35100 İzmir, Turkey
^*Correspondence e-mail: namiko@omu.edu.tr

(Received 15 January 2008; accepted 16 January 2008; online 23 January 2008)

In the title complex, [Pd₂(C₁₁H₈N)₂(C₂H₃O₂)₂], each Pd^II ion has a distorted square-planar environment, being surrounded by one C, one N and two O atoms. The Pd⋯Pd distance is 2.8721 (3) Å. In the crystal structure, the molecules are linked by intermolecular C—H⋯O interactions.

Related literature

For related compounds, see: Cravotto et al. (2005 ). For the synthesis, see: Aiello et al. (2000 ). For background information on graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

[Pd₂(C₁₁H₈N)₂(C₂H₃O₂)₂]
M_r = 639.26
Monoclinic, P 2₁ /c
a = 9.7160 (3) Å
b = 19.1986 (5) Å
c = 14.4990 (4) Å
β = 119.451 (2)°
V = 2355.06 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.56 mm⁻¹
T = 296 K
0.46 × 0.31 × 0.22 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED; Stoe & Cie, 2002 ) T_min = 0.355, T_max = 0.728
23605 measured reflections
5011 independent reflections
4375 reflections with I > 2σ(I)
R_int = 0.136

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.071
S = 1.05
5011 reflections
309 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond lengths (Å)

Pd1—C11	1.960 (3)
Pd1—N1	2.006 (2)
Pd1—O2	2.052 (2)
Pd1—O1	2.143 (2)
Pd2—N2	1.961 (3)
Pd2—C24	2.002 (3)
Pd2—O3	2.058 (2)
Pd2—O4	2.155 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.93	2.56	3.134 (4)	120
C23—H23⋯O4	0.93	2.57	3.146 (4)	120
C14—H14⋯O3	0.93	2.54	3.054 (5)	115
C10—H10⋯O2	0.93	2.56	3.069 (4)	115
C7—H7⋯O3ⁱ	0.93	2.56	3.344 (4)	142
Symmetry code: (i) x+1, y, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001736/hb2692sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001736/hb2692Isup2.hkl

checkCIF report

Comment top

Cyclometalated compounds are organometallic complexes embodying an E—M—C connectivity of σ-bonds, where E is a heterodonor atom of the 15- or 16-group, M is a metallic atom and C is a carbon donor. They are usually classified according to the metal, the donor atom(s) or chelate ring size. Cyclometalated compounds with a variety of N-donor ligands have been extensively investigated (Cravotto et al., 2005).

The structure of the title dinuclear complex, (I), is shown in Fig. 1. The coordination around the Pd^II ions is distorted square-planar, and each Pd^II ion is coordinated by one pyridine N atom and one aryl C atom from the phenylpyridine ligand and two O atoms from two acetate ligands (Table 1). The pyridine N– and aryl C-donor atoms form two five-membered metallacycles (containing atoms N1/C5/C6/C11/Pd1 and N2/C18/C19/C24/Pd2) with maximum deviations from planarity being -0.033 (2) and 0.0399 (2) Å for atoms N1 and C24, respectively. The separation of the Pd centres in the moleucle of (I) is a relatively short 2.8721 (3) Å.

Four short C—H···O intramolecular interactions (Table 2) are observed between the phenylpyridine H atoms and acetate O atoms, all of which lead to the formation of a five-membered ring with graph-set descriptor S(5) (Bernstein et al., 1995). In the crystal structure of (I), an intermolecular C—H···O interaction involving an aryl C—H donor and acetate acceptor is seen. Propagation of this hydrogen bond by translation then generates a C(8) chain running parallel to the [100] direction (Fig. 2). There are no other significant directional interactions in the crystal of (I).

Related literature top

For related compounds, see: Cravotto et al. (2005). For the synthesis, see: Aiello et al. (2000). For background information on graph-set theory, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized according to a modification of literature methods (Aiello et al., 2000) and colourless prisms of (I) were grown from CH₂Cl₂/hexane (1:3 v/v).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. A view of the molecular structure of (I), showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. Part of the crystal structure of (I), showing a C(8) chain along [100]. For the sake of clarity, only H atoms involved in hydrogen bonding have been included.

Di-µ-acetato-κ⁴O:O'-bis{[2-(2-pyridyl)phenyl-κ²C,N]palladium(II)} top

Crystal data top

[Pd₂(C₁₁H₈N)₂(C₂H₃O₂)₂]	F(000) = 1264
M_r = 639.26	D_x = 1.803 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 33146 reflections
a = 9.7160 (3) Å	θ = 1.6–27.3°
b = 19.1986 (5) Å	µ = 1.56 mm⁻¹
c = 14.4990 (4) Å	T = 296 K
β = 119.451 (2)°	Prism, colorless
V = 2355.06 (12) Å³	0.46 × 0.31 × 0.22 mm
Z = 4

Data collection top

Stoe IPDSII diffractometer	5011 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4375 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.136
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.8°, θ_min = 1.9°
ω scans	h = −12→12
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −24→24
T_min = 0.355, T_max = 0.728	l = −18→18
23605 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0408P)² + 0.5683P] where P = (F_o² + 2F_c²)/3
5011 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.77 e Å⁻³
2 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Pd₂(C₁₁H₈N)₂(C₂H₃O₂)₂]	V = 2355.06 (12) Å³
M_r = 639.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7160 (3) Å	µ = 1.56 mm⁻¹
b = 19.1986 (5) Å	T = 296 K
c = 14.4990 (4) Å	0.46 × 0.31 × 0.22 mm
β = 119.451 (2)°

Data collection top

Stoe IPDSII diffractometer	5011 independent reflections
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	4375 reflections with I > 2σ(I)
T_min = 0.355, T_max = 0.728	R_int = 0.136
23605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	2 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.05	Δρ_max = 0.77 e Å⁻³
5011 reflections	Δρ_min = −0.37 e Å⁻³
309 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Pd1	0.46714 (2)	0.310590 (12)	0.223710 (16)	0.04341 (7)
Pd2	0.37093 (2)	0.410977 (12)	0.327729 (17)	0.04429 (7)
O1	0.3311 (3)	0.24915 (12)	0.27333 (19)	0.0561 (5)
O2	0.2637 (2)	0.33997 (13)	0.09023 (16)	0.0557 (5)
O3	0.2400 (3)	0.33063 (12)	0.33927 (19)	0.0587 (5)
O4	0.1952 (2)	0.42585 (12)	0.16407 (17)	0.0578 (5)
N1	0.6762 (3)	0.28819 (13)	0.35073 (19)	0.0477 (5)
N2	0.5367 (4)	0.40253 (16)	0.4762 (2)	0.0630 (7)
C1	0.6946 (4)	0.25087 (19)	0.4345 (3)	0.0604 (8)
H1	0.6069	0.2296	0.4321	0.072*
C2	0.8396 (5)	0.2433 (2)	0.5233 (3)	0.0738 (10)
H2	0.8497	0.2178	0.5809	0.089*
C3	0.9692 (5)	0.2737 (2)	0.5265 (3)	0.0725 (10)
H3	1.0684	0.2688	0.5860	0.087*
C4	0.9516 (4)	0.31178 (19)	0.4409 (3)	0.0628 (9)
H4	1.0391	0.3324	0.4421	0.075*
C5	0.8032 (3)	0.31928 (16)	0.3532 (2)	0.0483 (7)
C6	0.7649 (3)	0.35957 (16)	0.2578 (2)	0.0481 (6)
C7	0.8747 (4)	0.3950 (2)	0.2408 (3)	0.0626 (8)
H7	0.9813	0.3938	0.2915	0.075*
C8	0.8254 (5)	0.4318 (2)	0.1492 (4)	0.0744 (10)
H8	0.8987	0.4565	0.1384	0.089*
C9	0.6682 (5)	0.4327 (2)	0.0726 (3)	0.0735 (10)
H9	0.6363	0.4574	0.0101	0.088*
C10	0.5574 (4)	0.3970 (2)	0.0883 (3)	0.0608 (8)
H10	0.4515	0.3977	0.0362	0.073*
C11	0.6038 (3)	0.36020 (16)	0.1816 (2)	0.0458 (6)
C12	0.2494 (3)	0.26915 (17)	0.3132 (2)	0.0481 (6)
C13	0.1557 (5)	0.2155 (2)	0.3327 (3)	0.0698 (9)
H13A	0.0459	0.2281	0.2955	0.105*
H13B	0.1916	0.2128	0.4072	0.105*
H13C	0.1694	0.1710	0.3079	0.105*
C14	0.5364 (5)	0.35817 (19)	0.5515 (3)	0.0684 (9)
H14	0.4499	0.3295	0.5341	0.082*
C15	0.6653 (7)	0.3566 (3)	0.6527 (3)	0.0889 (14)
H15	0.6651	0.3266	0.7029	0.107*
C16	0.7926 (6)	0.3987 (3)	0.6796 (3)	0.0928 (15)
H16	0.8782	0.3970	0.7480	0.111*
C17	0.7961 (5)	0.4436 (2)	0.6071 (3)	0.0780 (11)
H17	0.8829	0.4724	0.6262	0.094*
C18	0.6680 (4)	0.44554 (18)	0.5045 (2)	0.0557 (7)
C19	0.6545 (4)	0.49149 (18)	0.4208 (3)	0.0573 (8)
C20	0.7699 (5)	0.5372 (3)	0.4277 (4)	0.0861 (12)
H20	0.8667	0.5403	0.4898	0.103*
C21	0.7393 (7)	0.5778 (3)	0.3416 (4)	0.1022 (17)
H21	0.8159	0.6083	0.3449	0.123*
C22	0.5970 (7)	0.5733 (3)	0.2518 (4)	0.0976 (15)
H22	0.5747	0.6014	0.1938	0.117*
C23	0.4870 (5)	0.5270 (2)	0.2474 (3)	0.0681 (9)
H23	0.3900	0.5237	0.1856	0.082*
C24	0.5157 (3)	0.48611 (14)	0.3303 (2)	0.0416 (5)
C25	0.1765 (3)	0.38936 (17)	0.0883 (2)	0.0474 (6)
C26	0.0362 (4)	0.4046 (2)	−0.0187 (3)	0.0638 (9)
H26A	0.0063	0.3631	−0.0611	0.096*
H26B	0.0635	0.4403	−0.0532	0.096*
H26C	−0.0506	0.4201	−0.0100	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.03742 (11)	0.05360 (14)	0.03992 (12)	0.00322 (8)	0.01957 (9)	0.00016 (9)
Pd2	0.04767 (12)	0.04564 (13)	0.03768 (12)	−0.00157 (9)	0.01955 (9)	−0.00403 (8)
O1	0.0602 (12)	0.0562 (13)	0.0631 (14)	−0.0076 (10)	0.0389 (11)	−0.0048 (10)
O2	0.0432 (10)	0.0747 (15)	0.0419 (11)	0.0066 (10)	0.0152 (9)	−0.0035 (10)
O3	0.0604 (12)	0.0579 (14)	0.0684 (14)	−0.0080 (10)	0.0398 (12)	−0.0069 (11)
O4	0.0537 (11)	0.0646 (14)	0.0418 (11)	0.0053 (10)	0.0132 (9)	−0.0057 (10)
N1	0.0469 (12)	0.0501 (14)	0.0432 (13)	0.0082 (10)	0.0199 (10)	0.0013 (10)
N2	0.0736 (17)	0.0631 (18)	0.0487 (15)	0.0099 (13)	0.0274 (14)	−0.0043 (12)
C1	0.0651 (19)	0.063 (2)	0.0504 (18)	0.0116 (16)	0.0263 (15)	0.0092 (15)
C2	0.090 (3)	0.066 (2)	0.051 (2)	0.020 (2)	0.0230 (19)	0.0106 (17)
C3	0.065 (2)	0.071 (2)	0.053 (2)	0.0180 (18)	0.0063 (16)	−0.0018 (17)
C4	0.0477 (16)	0.068 (2)	0.0557 (19)	0.0065 (14)	0.0123 (14)	−0.0086 (16)
C5	0.0424 (13)	0.0499 (17)	0.0481 (16)	0.0068 (11)	0.0186 (12)	−0.0059 (12)
C6	0.0415 (13)	0.0537 (17)	0.0526 (16)	0.0023 (12)	0.0257 (12)	−0.0072 (13)
C7	0.0514 (16)	0.069 (2)	0.073 (2)	−0.0041 (15)	0.0350 (16)	−0.0075 (18)
C8	0.073 (2)	0.080 (3)	0.094 (3)	−0.0062 (19)	0.059 (2)	0.003 (2)
C9	0.088 (3)	0.079 (3)	0.072 (2)	0.006 (2)	0.053 (2)	0.018 (2)
C10	0.0582 (17)	0.076 (2)	0.0517 (18)	0.0060 (16)	0.0297 (15)	0.0098 (16)
C11	0.0439 (13)	0.0539 (17)	0.0433 (14)	0.0059 (12)	0.0242 (12)	−0.0004 (12)
C12	0.0460 (14)	0.0577 (19)	0.0417 (14)	−0.0087 (12)	0.0224 (12)	−0.0016 (13)
C13	0.081 (2)	0.068 (2)	0.079 (2)	−0.0179 (18)	0.054 (2)	−0.0039 (19)
C14	0.098 (3)	0.058 (2)	0.0485 (18)	0.0091 (18)	0.0361 (18)	0.0047 (15)
C15	0.128 (4)	0.081 (3)	0.048 (2)	0.032 (3)	0.036 (2)	0.0149 (19)
C16	0.099 (3)	0.103 (4)	0.043 (2)	0.033 (3)	0.010 (2)	0.001 (2)
C17	0.062 (2)	0.094 (3)	0.053 (2)	0.0101 (19)	0.0091 (17)	−0.014 (2)
C18	0.0552 (16)	0.0581 (19)	0.0430 (15)	0.0067 (13)	0.0158 (13)	−0.0094 (14)
C19	0.0600 (17)	0.0573 (19)	0.0545 (18)	−0.0082 (14)	0.0280 (15)	−0.0130 (15)
C20	0.076 (2)	0.095 (3)	0.080 (3)	−0.032 (2)	0.032 (2)	−0.022 (2)
C21	0.113 (4)	0.108 (4)	0.094 (4)	−0.057 (3)	0.057 (3)	−0.016 (3)
C22	0.135 (4)	0.085 (3)	0.080 (3)	−0.041 (3)	0.058 (3)	−0.004 (2)
C23	0.084 (2)	0.060 (2)	0.0573 (19)	−0.0155 (18)	0.0328 (18)	−0.0033 (15)
C24	0.0495 (14)	0.0367 (13)	0.0384 (13)	−0.0045 (11)	0.0214 (11)	−0.0059 (10)
C25	0.0419 (13)	0.0567 (17)	0.0392 (14)	−0.0024 (12)	0.0166 (11)	0.0028 (12)
C26	0.0583 (18)	0.073 (2)	0.0446 (17)	0.0090 (16)	0.0130 (14)	0.0026 (15)

Geometric parameters (Å, º) top

Pd1—C11	1.960 (3)	C9—C10	1.387 (5)
Pd1—N1	2.006 (2)	C9—H9	0.9300
Pd1—O2	2.052 (2)	C10—C11	1.390 (4)
Pd1—O1	2.143 (2)	C10—H10	0.9300
Pd1—Pd2	2.8721 (3)	C12—C13	1.491 (4)
Pd2—N2	1.961 (3)	C13—H13A	0.9600
Pd2—C24	2.002 (3)	C13—H13B	0.9600
Pd2—O3	2.058 (2)	C13—H13C	0.9600
Pd2—O4	2.155 (2)	C14—C15	1.384 (6)
O1—C12	1.250 (4)	C14—H14	0.9300
O2—C25	1.262 (4)	C15—C16	1.364 (7)
O3—C12	1.256 (4)	C15—H15	0.9300
O4—C25	1.239 (4)	C16—C17	1.372 (7)
N1—C1	1.344 (4)	C16—H16	0.9300
N1—C5	1.356 (4)	C17—C18	1.394 (5)
N2—C14	1.386 (5)	C17—H17	0.9300
N2—C18	1.401 (5)	C18—C19	1.453 (5)
C1—C2	1.371 (5)	C19—C24	1.346 (4)
C1—H1	0.9300	C19—C20	1.388 (5)
C2—C3	1.368 (6)	C20—C21	1.374 (7)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.376 (6)	C21—C22	1.358 (7)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.384 (4)	C22—C23	1.367 (6)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.464 (4)	C23—C24	1.345 (5)
C6—C7	1.386 (4)	C23—H23	0.9300
C6—C11	1.404 (4)	C25—C26	1.507 (4)
C7—C8	1.367 (6)	C26—H26A	0.9600
C7—H7	0.9300	C26—H26B	0.9600
C8—C9	1.377 (6)	C26—H26C	0.9600
C8—H8	0.9300

C11—Pd1—N1	81.67 (11)	C9—C10—C11	120.3 (3)
C11—Pd1—O2	93.36 (10)	C9—C10—H10	119.8
N1—Pd1—O2	174.91 (10)	C11—C10—H10	119.8
C11—Pd1—O1	175.22 (10)	C10—C11—C6	118.2 (3)
N1—Pd1—O1	94.99 (10)	C10—C11—Pd1	127.2 (2)
O2—Pd1—O1	90.03 (9)	C6—C11—Pd1	114.5 (2)
C11—Pd1—Pd2	106.43 (9)	O1—C12—O3	125.7 (3)
N1—Pd1—Pd2	96.07 (7)	O1—C12—C13	117.4 (3)
O2—Pd1—Pd2	84.23 (6)	O3—C12—C13	116.8 (3)
O1—Pd1—Pd2	77.25 (6)	C12—C13—H13A	109.5
N2—Pd2—C24	81.30 (12)	C12—C13—H13B	109.5
N2—Pd2—O3	93.19 (12)	H13A—C13—H13B	109.5
C24—Pd2—O3	174.36 (10)	C12—C13—H13C	109.5
N2—Pd2—O4	176.64 (11)	H13A—C13—H13C	109.5
C24—Pd2—O4	95.39 (10)	H13B—C13—H13C	109.5
O3—Pd2—O4	90.13 (9)	C15—C14—N2	119.8 (4)
N2—Pd2—Pd1	102.55 (8)	C15—C14—H14	120.1
C24—Pd2—Pd1	94.94 (8)	N2—C14—H14	120.1
O3—Pd2—Pd1	85.04 (6)	C16—C15—C14	120.7 (4)
O4—Pd2—Pd1	78.28 (6)	C16—C15—H15	119.6
C12—O1—Pd1	128.5 (2)	C14—C15—H15	119.6
C25—O2—Pd1	123.52 (19)	C15—C16—C17	120.9 (4)
C12—O3—Pd2	122.73 (19)	C15—C16—H16	119.6
C25—O4—Pd2	126.4 (2)	C17—C16—H16	119.6
C1—N1—C5	119.7 (3)	C16—C17—C18	119.3 (4)
C1—N1—Pd1	124.7 (2)	C16—C17—H17	120.4
C5—N1—Pd1	115.3 (2)	C18—C17—H17	120.4
C14—N2—C18	119.0 (3)	C17—C18—N2	120.2 (4)
C14—N2—Pd2	126.7 (3)	C17—C18—C19	125.1 (4)
C18—N2—Pd2	114.3 (2)	N2—C18—C19	114.7 (3)
N1—C1—C2	121.6 (4)	C24—C19—C20	120.4 (4)
N1—C1—H1	119.2	C24—C19—C18	113.8 (3)
C2—C1—H1	119.2	C20—C19—C18	125.8 (3)
C3—C2—C1	119.4 (4)	C21—C20—C19	119.1 (4)
C3—C2—H2	120.3	C21—C20—H20	120.5
C1—C2—H2	120.3	C19—C20—H20	120.5
C2—C3—C4	119.5 (3)	C22—C21—C20	119.9 (4)
C2—C3—H3	120.3	C22—C21—H21	120.0
C4—C3—H3	120.3	C20—C21—H21	120.0
C3—C4—C5	119.7 (4)	C21—C22—C23	119.3 (4)
C3—C4—H4	120.1	C21—C22—H22	120.3
C5—C4—H4	120.1	C23—C22—H22	120.3
N1—C5—C4	120.1 (3)	C24—C23—C22	121.6 (4)
N1—C5—C6	113.7 (2)	C24—C23—H23	119.2
C4—C5—C6	126.2 (3)	C22—C23—H23	119.2
C7—C6—C11	120.9 (3)	C23—C24—C19	119.7 (3)
C7—C6—C5	124.5 (3)	C23—C24—Pd2	124.7 (2)
C11—C6—C5	114.6 (3)	C19—C24—Pd2	115.5 (2)
C8—C7—C6	119.6 (3)	O4—C25—O2	126.9 (3)
C8—C7—H7	120.2	O4—C25—C26	117.8 (3)
C6—C7—H7	120.2	O2—C25—C26	115.2 (3)
C7—C8—C9	120.7 (3)	C25—C26—H26A	109.5
C7—C8—H8	119.7	C25—C26—H26B	109.5
C9—C8—H8	119.7	H26A—C26—H26B	109.5
C8—C9—C10	120.2 (4)	C25—C26—H26C	109.5
C8—C9—H9	119.9	H26A—C26—H26C	109.5
C10—C9—H9	119.9	H26B—C26—H26C	109.5

C11—Pd1—Pd2—N2	−90.26 (13)	C5—C6—C7—C8	−179.2 (3)
N1—Pd1—Pd2—N2	−7.18 (12)	C6—C7—C8—C9	−1.4 (6)
O2—Pd1—Pd2—N2	177.93 (12)	C7—C8—C9—C10	0.9 (6)
O1—Pd1—Pd2—N2	86.58 (12)	C8—C9—C10—C11	0.2 (6)
C11—Pd1—Pd2—C24	−8.09 (11)	C9—C10—C11—C6	−0.8 (5)
N1—Pd1—Pd2—C24	74.99 (11)	C9—C10—C11—Pd1	176.4 (3)
O2—Pd1—Pd2—C24	−99.90 (10)	C7—C6—C11—C10	0.4 (5)
O1—Pd1—Pd2—C24	168.75 (10)	C5—C6—C11—C10	−179.7 (3)
C11—Pd1—Pd2—O3	177.57 (11)	C7—C6—C11—Pd1	−177.3 (2)
N1—Pd1—Pd2—O3	−99.35 (10)	C5—C6—C11—Pd1	2.7 (3)
O2—Pd1—Pd2—O3	85.76 (10)	N1—Pd1—C11—C10	178.7 (3)
O1—Pd1—Pd2—O3	−5.59 (9)	O2—Pd1—C11—C10	−2.4 (3)
C11—Pd1—Pd2—O4	86.40 (11)	Pd2—Pd1—C11—C10	−87.4 (3)
N1—Pd1—Pd2—O4	169.48 (10)	N1—Pd1—C11—C6	−3.9 (2)
O2—Pd1—Pd2—O4	−5.41 (9)	O2—Pd1—C11—C6	175.0 (2)
O1—Pd1—Pd2—O4	−96.75 (9)	Pd2—Pd1—C11—C6	90.0 (2)
N1—Pd1—O1—C12	102.8 (3)	Pd1—O1—C12—O3	−5.4 (5)
O2—Pd1—O1—C12	−76.3 (3)	Pd1—O1—C12—C13	175.2 (2)
Pd2—Pd1—O1—C12	7.7 (2)	Pd2—O3—C12—O1	−3.4 (4)
C11—Pd1—O2—C25	−100.1 (3)	Pd2—O3—C12—C13	176.0 (2)
O1—Pd1—O2—C25	83.3 (2)	C18—N2—C14—C15	−0.4 (5)
Pd2—Pd1—O2—C25	6.1 (2)	Pd2—N2—C14—C15	177.9 (3)
N2—Pd2—O3—C12	−95.5 (3)	N2—C14—C15—C16	0.4 (6)
O4—Pd2—O3—C12	85.1 (2)	C14—C15—C16—C17	0.0 (7)
Pd1—Pd2—O3—C12	6.8 (2)	C15—C16—C17—C18	−0.5 (7)
C24—Pd2—O4—C25	101.8 (3)	C16—C17—C18—N2	0.6 (6)
O3—Pd2—O4—C25	−77.1 (3)	C16—C17—C18—C19	178.5 (4)
Pd1—Pd2—O4—C25	7.8 (2)	C14—N2—C18—C17	−0.1 (5)
C11—Pd1—N1—C1	178.4 (3)	Pd2—N2—C18—C17	−178.6 (3)
O1—Pd1—N1—C1	−5.0 (3)	C14—N2—C18—C19	−178.3 (3)
Pd2—Pd1—N1—C1	72.7 (3)	Pd2—N2—C18—C19	3.3 (4)
C11—Pd1—N1—C5	4.7 (2)	C17—C18—C19—C24	−176.6 (3)
O1—Pd1—N1—C5	−178.8 (2)	N2—C18—C19—C24	1.4 (4)
Pd2—Pd1—N1—C5	−101.1 (2)	C17—C18—C19—C20	4.2 (6)
C24—Pd2—N2—C14	176.9 (3)	N2—C18—C19—C20	−177.7 (4)
O3—Pd2—N2—C14	−4.3 (3)	C24—C19—C20—C21	1.3 (7)
Pd1—Pd2—N2—C14	−89.9 (3)	C18—C19—C20—C21	−179.6 (4)
C24—Pd2—N2—C18	−4.7 (2)	C19—C20—C21—C22	0.6 (8)
O3—Pd2—N2—C18	174.0 (2)	C20—C21—C22—C23	−1.5 (9)
Pd1—Pd2—N2—C18	88.4 (2)	C21—C22—C23—C24	0.5 (8)
C5—N1—C1—C2	0.1 (5)	C22—C23—C24—C19	1.4 (6)
Pd1—N1—C1—C2	−173.4 (3)	C22—C23—C24—Pd2	−174.3 (3)
N1—C1—C2—C3	−0.9 (6)	C20—C19—C24—C23	−2.3 (5)
C1—C2—C3—C4	0.5 (6)	C18—C19—C24—C23	178.6 (3)
C2—C3—C4—C5	0.5 (5)	C20—C19—C24—Pd2	173.8 (3)
C1—N1—C5—C4	0.9 (4)	C18—C19—C24—Pd2	−5.4 (4)
Pd1—N1—C5—C4	175.0 (2)	N2—Pd2—C24—C23	−178.5 (3)
C1—N1—C5—C6	−178.5 (3)	O4—Pd2—C24—C23	0.9 (3)
Pd1—N1—C5—C6	−4.4 (3)	Pd1—Pd2—C24—C23	79.5 (3)
C3—C4—C5—N1	−1.2 (5)	N2—Pd2—C24—C19	5.7 (2)
C3—C4—C5—C6	178.1 (3)	O4—Pd2—C24—C19	−174.9 (2)
N1—C5—C6—C7	−178.9 (3)	Pd1—Pd2—C24—C19	−96.2 (2)
C4—C5—C6—C7	1.7 (5)	Pd2—O4—C25—O2	−6.2 (5)
N1—C5—C6—C11	1.1 (4)	Pd2—O4—C25—C26	174.2 (2)
C4—C5—C6—C11	−178.2 (3)	Pd1—O2—C25—O4	−2.2 (5)
C11—C6—C7—C8	0.8 (5)	Pd1—O2—C25—C26	177.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.93	2.56	3.134 (4)	120
C23—H23···O4	0.93	2.57	3.146 (4)	120
C14—H14···O3	0.93	2.54	3.054 (5)	115
C10—H10···O2	0.93	2.56	3.069 (4)	115
C7—H7···O3ⁱ	0.93	2.56	3.344 (4)	142

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

Experimental details

Crystal data
Chemical formula	[Pd₂(C₁₁H₈N)₂(C₂H₃O₂)₂]
M_r	639.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.7160 (3), 19.1986 (5), 14.4990 (4)
β (°)	119.451 (2)
V (Å³)	2355.06 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.46 × 0.31 × 0.22

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED; Stoe & Cie, 2002)
T_min, T_max	0.355, 0.728
No. of measured, independent and observed [I > 2σ(I)] reflections	23605, 5011, 4375
R_int	0.136
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.071, 1.05
No. of reflections	5011
No. of parameters	309
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.37

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Selected bond lengths (Å) top

Pd1—C11	1.960 (3)	Pd2—N2	1.961 (3)
Pd1—N1	2.006 (2)	Pd2—C24	2.002 (3)
Pd1—O2	2.052 (2)	Pd2—O3	2.058 (2)
Pd1—O1	2.143 (2)	Pd2—O4	2.155 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.93	2.56	3.134 (4)	120
C23—H23···O4	0.93	2.57	3.146 (4)	120
C14—H14···O3	0.93	2.54	3.054 (5)	115
C10—H10···O2	0.93	2.56	3.069 (4)	115
C7—H7···O3ⁱ	0.93	2.56	3.344 (4)	142

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

Acknowledgements

This study was supported financially by the Research Center of Ondokuz Mayıs University (project No. F-425).

References

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