metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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 PdII 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[Cravotto, G., Demartin, F., Palmisano, G., Penoni, A., Radice, T. & Tollari, S. (2005). J. Organomet. Chem. 690, 2017-2026.]). For the synthesis, see: Aiello et al. (2000[Aiello, I., Crispini, A., Ghedini, M., La Deda, M. & Barigelletti, F. (2000). Inorg. Chim. Acta, 308, 121-128.]). For background information on graph-set theory, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • [Pd2(C11H8N)2(C2H3O2)2]

  • Mr = 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[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED (Version 1.04). Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.355, Tmax = 0.728

  • 23605 measured reflections

  • 5011 independent reflections

  • 4375 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.77 e Å−3

  • Δρmin = −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 DA 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[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED (Version 1.04). Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED (Version 1.04). Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


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 PdII ions is distorted square-planar, and each PdII 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).

Refinement top

The H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate, but not to tip, to best fit the electron density.

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
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] 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
Mr = 639.26Dx = 1.803 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 33146 reflections
a = 9.7160 (3) Åθ = 1.6–27.3°
b = 19.1986 (5) ŵ = 1.56 mm1
c = 14.4990 (4) ÅT = 296 K
β = 119.451 (2)°Prism, colorless
V = 2355.06 (12) Å30.46 × 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 focus4375 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.136
Detector resolution: 6.67 pixels mm-1θmax = 26.8°, θmin = 1.9°
ω scansh = 1212
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 2424
Tmin = 0.355, Tmax = 0.728l = 1818
23605 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0408P)2 + 0.5683P]
where P = (Fo2 + 2Fc2)/3
5011 reflections(Δ/σ)max = 0.001
309 parametersΔρmax = 0.77 e Å3
2 restraintsΔρmin = 0.37 e Å3
Crystal data top
[Pd2(C11H8N)2(C2H3O2)2]V = 2355.06 (12) Å3
Mr = 639.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.7160 (3) ŵ = 1.56 mm1
b = 19.1986 (5) ÅT = 296 K
c = 14.4990 (4) Å0.46 × 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)
Tmin = 0.355, Tmax = 0.728Rint = 0.136
23605 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0322 restraints
wR(F2) = 0.071H-atom parameters constrained
S = 1.05Δρmax = 0.77 e Å3
5011 reflectionsΔρmin = 0.37 e Å3
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
xyzUiso*/Ueq
Pd10.46714 (2)0.310590 (12)0.223710 (16)0.04341 (7)
Pd20.37093 (2)0.410977 (12)0.327729 (17)0.04429 (7)
O10.3311 (3)0.24915 (12)0.27333 (19)0.0561 (5)
O20.2637 (2)0.33997 (13)0.09023 (16)0.0557 (5)
O30.2400 (3)0.33063 (12)0.33927 (19)0.0587 (5)
O40.1952 (2)0.42585 (12)0.16407 (17)0.0578 (5)
N10.6762 (3)0.28819 (13)0.35073 (19)0.0477 (5)
N20.5367 (4)0.40253 (16)0.4762 (2)0.0630 (7)
C10.6946 (4)0.25087 (19)0.4345 (3)0.0604 (8)
H10.60690.22960.43210.072*
C20.8396 (5)0.2433 (2)0.5233 (3)0.0738 (10)
H20.84970.21780.58090.089*
C30.9692 (5)0.2737 (2)0.5265 (3)0.0725 (10)
H31.06840.26880.58600.087*
C40.9516 (4)0.31178 (19)0.4409 (3)0.0628 (9)
H41.03910.33240.44210.075*
C50.8032 (3)0.31928 (16)0.3532 (2)0.0483 (7)
C60.7649 (3)0.35957 (16)0.2578 (2)0.0481 (6)
C70.8747 (4)0.3950 (2)0.2408 (3)0.0626 (8)
H70.98130.39380.29150.075*
C80.8254 (5)0.4318 (2)0.1492 (4)0.0744 (10)
H80.89870.45650.13840.089*
C90.6682 (5)0.4327 (2)0.0726 (3)0.0735 (10)
H90.63630.45740.01010.088*
C100.5574 (4)0.3970 (2)0.0883 (3)0.0608 (8)
H100.45150.39770.03620.073*
C110.6038 (3)0.36020 (16)0.1816 (2)0.0458 (6)
C120.2494 (3)0.26915 (17)0.3132 (2)0.0481 (6)
C130.1557 (5)0.2155 (2)0.3327 (3)0.0698 (9)
H13A0.04590.22810.29550.105*
H13B0.19160.21280.40720.105*
H13C0.16940.17100.30790.105*
C140.5364 (5)0.35817 (19)0.5515 (3)0.0684 (9)
H140.44990.32950.53410.082*
C150.6653 (7)0.3566 (3)0.6527 (3)0.0889 (14)
H150.66510.32660.70290.107*
C160.7926 (6)0.3987 (3)0.6796 (3)0.0928 (15)
H160.87820.39700.74800.111*
C170.7961 (5)0.4436 (2)0.6071 (3)0.0780 (11)
H170.88290.47240.62620.094*
C180.6680 (4)0.44554 (18)0.5045 (2)0.0557 (7)
C190.6545 (4)0.49149 (18)0.4208 (3)0.0573 (8)
C200.7699 (5)0.5372 (3)0.4277 (4)0.0861 (12)
H200.86670.54030.48980.103*
C210.7393 (7)0.5778 (3)0.3416 (4)0.1022 (17)
H210.81590.60830.34490.123*
C220.5970 (7)0.5733 (3)0.2518 (4)0.0976 (15)
H220.57470.60140.19380.117*
C230.4870 (5)0.5270 (2)0.2474 (3)0.0681 (9)
H230.39000.52370.18560.082*
C240.5157 (3)0.48611 (14)0.3303 (2)0.0416 (5)
C250.1765 (3)0.38936 (17)0.0883 (2)0.0474 (6)
C260.0362 (4)0.4046 (2)0.0187 (3)0.0638 (9)
H26A0.00630.36310.06110.096*
H26B0.06350.44030.05320.096*
H26C0.05060.42010.01000.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.03742 (11)0.05360 (14)0.03992 (12)0.00322 (8)0.01957 (9)0.00016 (9)
Pd20.04767 (12)0.04564 (13)0.03768 (12)0.00157 (9)0.01955 (9)0.00403 (8)
O10.0602 (12)0.0562 (13)0.0631 (14)0.0076 (10)0.0389 (11)0.0048 (10)
O20.0432 (10)0.0747 (15)0.0419 (11)0.0066 (10)0.0152 (9)0.0035 (10)
O30.0604 (12)0.0579 (14)0.0684 (14)0.0080 (10)0.0398 (12)0.0069 (11)
O40.0537 (11)0.0646 (14)0.0418 (11)0.0053 (10)0.0132 (9)0.0057 (10)
N10.0469 (12)0.0501 (14)0.0432 (13)0.0082 (10)0.0199 (10)0.0013 (10)
N20.0736 (17)0.0631 (18)0.0487 (15)0.0099 (13)0.0274 (14)0.0043 (12)
C10.0651 (19)0.063 (2)0.0504 (18)0.0116 (16)0.0263 (15)0.0092 (15)
C20.090 (3)0.066 (2)0.051 (2)0.020 (2)0.0230 (19)0.0106 (17)
C30.065 (2)0.071 (2)0.053 (2)0.0180 (18)0.0063 (16)0.0018 (17)
C40.0477 (16)0.068 (2)0.0557 (19)0.0065 (14)0.0123 (14)0.0086 (16)
C50.0424 (13)0.0499 (17)0.0481 (16)0.0068 (11)0.0186 (12)0.0059 (12)
C60.0415 (13)0.0537 (17)0.0526 (16)0.0023 (12)0.0257 (12)0.0072 (13)
C70.0514 (16)0.069 (2)0.073 (2)0.0041 (15)0.0350 (16)0.0075 (18)
C80.073 (2)0.080 (3)0.094 (3)0.0062 (19)0.059 (2)0.003 (2)
C90.088 (3)0.079 (3)0.072 (2)0.006 (2)0.053 (2)0.018 (2)
C100.0582 (17)0.076 (2)0.0517 (18)0.0060 (16)0.0297 (15)0.0098 (16)
C110.0439 (13)0.0539 (17)0.0433 (14)0.0059 (12)0.0242 (12)0.0004 (12)
C120.0460 (14)0.0577 (19)0.0417 (14)0.0087 (12)0.0224 (12)0.0016 (13)
C130.081 (2)0.068 (2)0.079 (2)0.0179 (18)0.054 (2)0.0039 (19)
C140.098 (3)0.058 (2)0.0485 (18)0.0091 (18)0.0361 (18)0.0047 (15)
C150.128 (4)0.081 (3)0.048 (2)0.032 (3)0.036 (2)0.0149 (19)
C160.099 (3)0.103 (4)0.043 (2)0.033 (3)0.010 (2)0.001 (2)
C170.062 (2)0.094 (3)0.053 (2)0.0101 (19)0.0091 (17)0.014 (2)
C180.0552 (16)0.0581 (19)0.0430 (15)0.0067 (13)0.0158 (13)0.0094 (14)
C190.0600 (17)0.0573 (19)0.0545 (18)0.0082 (14)0.0280 (15)0.0130 (15)
C200.076 (2)0.095 (3)0.080 (3)0.032 (2)0.032 (2)0.022 (2)
C210.113 (4)0.108 (4)0.094 (4)0.057 (3)0.057 (3)0.016 (3)
C220.135 (4)0.085 (3)0.080 (3)0.041 (3)0.058 (3)0.004 (2)
C230.084 (2)0.060 (2)0.0573 (19)0.0155 (18)0.0328 (18)0.0033 (15)
C240.0495 (14)0.0367 (13)0.0384 (13)0.0045 (11)0.0214 (11)0.0059 (10)
C250.0419 (13)0.0567 (17)0.0392 (14)0.0024 (12)0.0166 (11)0.0028 (12)
C260.0583 (18)0.073 (2)0.0446 (17)0.0090 (16)0.0130 (14)0.0026 (15)
Geometric parameters (Å, º) top
Pd1—C111.960 (3)C9—C101.387 (5)
Pd1—N12.006 (2)C9—H90.9300
Pd1—O22.052 (2)C10—C111.390 (4)
Pd1—O12.143 (2)C10—H100.9300
Pd1—Pd22.8721 (3)C12—C131.491 (4)
Pd2—N21.961 (3)C13—H13A0.9600
Pd2—C242.002 (3)C13—H13B0.9600
Pd2—O32.058 (2)C13—H13C0.9600
Pd2—O42.155 (2)C14—C151.384 (6)
O1—C121.250 (4)C14—H140.9300
O2—C251.262 (4)C15—C161.364 (7)
O3—C121.256 (4)C15—H150.9300
O4—C251.239 (4)C16—C171.372 (7)
N1—C11.344 (4)C16—H160.9300
N1—C51.356 (4)C17—C181.394 (5)
N2—C141.386 (5)C17—H170.9300
N2—C181.401 (5)C18—C191.453 (5)
C1—C21.371 (5)C19—C241.346 (4)
C1—H10.9300C19—C201.388 (5)
C2—C31.368 (6)C20—C211.374 (7)
C2—H20.9300C20—H200.9300
C3—C41.376 (6)C21—C221.358 (7)
C3—H30.9300C21—H210.9300
C4—C51.384 (4)C22—C231.367 (6)
C4—H40.9300C22—H220.9300
C5—C61.464 (4)C23—C241.345 (5)
C6—C71.386 (4)C23—H230.9300
C6—C111.404 (4)C25—C261.507 (4)
C7—C81.367 (6)C26—H26A0.9600
C7—H70.9300C26—H26B0.9600
C8—C91.377 (6)C26—H26C0.9600
C8—H80.9300
C11—Pd1—N181.67 (11)C9—C10—C11120.3 (3)
C11—Pd1—O293.36 (10)C9—C10—H10119.8
N1—Pd1—O2174.91 (10)C11—C10—H10119.8
C11—Pd1—O1175.22 (10)C10—C11—C6118.2 (3)
N1—Pd1—O194.99 (10)C10—C11—Pd1127.2 (2)
O2—Pd1—O190.03 (9)C6—C11—Pd1114.5 (2)
C11—Pd1—Pd2106.43 (9)O1—C12—O3125.7 (3)
N1—Pd1—Pd296.07 (7)O1—C12—C13117.4 (3)
O2—Pd1—Pd284.23 (6)O3—C12—C13116.8 (3)
O1—Pd1—Pd277.25 (6)C12—C13—H13A109.5
N2—Pd2—C2481.30 (12)C12—C13—H13B109.5
N2—Pd2—O393.19 (12)H13A—C13—H13B109.5
C24—Pd2—O3174.36 (10)C12—C13—H13C109.5
N2—Pd2—O4176.64 (11)H13A—C13—H13C109.5
C24—Pd2—O495.39 (10)H13B—C13—H13C109.5
O3—Pd2—O490.13 (9)C15—C14—N2119.8 (4)
N2—Pd2—Pd1102.55 (8)C15—C14—H14120.1
C24—Pd2—Pd194.94 (8)N2—C14—H14120.1
O3—Pd2—Pd185.04 (6)C16—C15—C14120.7 (4)
O4—Pd2—Pd178.28 (6)C16—C15—H15119.6
C12—O1—Pd1128.5 (2)C14—C15—H15119.6
C25—O2—Pd1123.52 (19)C15—C16—C17120.9 (4)
C12—O3—Pd2122.73 (19)C15—C16—H16119.6
C25—O4—Pd2126.4 (2)C17—C16—H16119.6
C1—N1—C5119.7 (3)C16—C17—C18119.3 (4)
C1—N1—Pd1124.7 (2)C16—C17—H17120.4
C5—N1—Pd1115.3 (2)C18—C17—H17120.4
C14—N2—C18119.0 (3)C17—C18—N2120.2 (4)
C14—N2—Pd2126.7 (3)C17—C18—C19125.1 (4)
C18—N2—Pd2114.3 (2)N2—C18—C19114.7 (3)
N1—C1—C2121.6 (4)C24—C19—C20120.4 (4)
N1—C1—H1119.2C24—C19—C18113.8 (3)
C2—C1—H1119.2C20—C19—C18125.8 (3)
C3—C2—C1119.4 (4)C21—C20—C19119.1 (4)
C3—C2—H2120.3C21—C20—H20120.5
C1—C2—H2120.3C19—C20—H20120.5
C2—C3—C4119.5 (3)C22—C21—C20119.9 (4)
C2—C3—H3120.3C22—C21—H21120.0
C4—C3—H3120.3C20—C21—H21120.0
C3—C4—C5119.7 (4)C21—C22—C23119.3 (4)
C3—C4—H4120.1C21—C22—H22120.3
C5—C4—H4120.1C23—C22—H22120.3
N1—C5—C4120.1 (3)C24—C23—C22121.6 (4)
N1—C5—C6113.7 (2)C24—C23—H23119.2
C4—C5—C6126.2 (3)C22—C23—H23119.2
C7—C6—C11120.9 (3)C23—C24—C19119.7 (3)
C7—C6—C5124.5 (3)C23—C24—Pd2124.7 (2)
C11—C6—C5114.6 (3)C19—C24—Pd2115.5 (2)
C8—C7—C6119.6 (3)O4—C25—O2126.9 (3)
C8—C7—H7120.2O4—C25—C26117.8 (3)
C6—C7—H7120.2O2—C25—C26115.2 (3)
C7—C8—C9120.7 (3)C25—C26—H26A109.5
C7—C8—H8119.7C25—C26—H26B109.5
C9—C8—H8119.7H26A—C26—H26B109.5
C8—C9—C10120.2 (4)C25—C26—H26C109.5
C8—C9—H9119.9H26A—C26—H26C109.5
C10—C9—H9119.9H26B—C26—H26C109.5
C11—Pd1—Pd2—N290.26 (13)C5—C6—C7—C8179.2 (3)
N1—Pd1—Pd2—N27.18 (12)C6—C7—C8—C91.4 (6)
O2—Pd1—Pd2—N2177.93 (12)C7—C8—C9—C100.9 (6)
O1—Pd1—Pd2—N286.58 (12)C8—C9—C10—C110.2 (6)
C11—Pd1—Pd2—C248.09 (11)C9—C10—C11—C60.8 (5)
N1—Pd1—Pd2—C2474.99 (11)C9—C10—C11—Pd1176.4 (3)
O2—Pd1—Pd2—C2499.90 (10)C7—C6—C11—C100.4 (5)
O1—Pd1—Pd2—C24168.75 (10)C5—C6—C11—C10179.7 (3)
C11—Pd1—Pd2—O3177.57 (11)C7—C6—C11—Pd1177.3 (2)
N1—Pd1—Pd2—O399.35 (10)C5—C6—C11—Pd12.7 (3)
O2—Pd1—Pd2—O385.76 (10)N1—Pd1—C11—C10178.7 (3)
O1—Pd1—Pd2—O35.59 (9)O2—Pd1—C11—C102.4 (3)
C11—Pd1—Pd2—O486.40 (11)Pd2—Pd1—C11—C1087.4 (3)
N1—Pd1—Pd2—O4169.48 (10)N1—Pd1—C11—C63.9 (2)
O2—Pd1—Pd2—O45.41 (9)O2—Pd1—C11—C6175.0 (2)
O1—Pd1—Pd2—O496.75 (9)Pd2—Pd1—C11—C690.0 (2)
N1—Pd1—O1—C12102.8 (3)Pd1—O1—C12—O35.4 (5)
O2—Pd1—O1—C1276.3 (3)Pd1—O1—C12—C13175.2 (2)
Pd2—Pd1—O1—C127.7 (2)Pd2—O3—C12—O13.4 (4)
C11—Pd1—O2—C25100.1 (3)Pd2—O3—C12—C13176.0 (2)
O1—Pd1—O2—C2583.3 (2)C18—N2—C14—C150.4 (5)
Pd2—Pd1—O2—C256.1 (2)Pd2—N2—C14—C15177.9 (3)
N2—Pd2—O3—C1295.5 (3)N2—C14—C15—C160.4 (6)
O4—Pd2—O3—C1285.1 (2)C14—C15—C16—C170.0 (7)
Pd1—Pd2—O3—C126.8 (2)C15—C16—C17—C180.5 (7)
C24—Pd2—O4—C25101.8 (3)C16—C17—C18—N20.6 (6)
O3—Pd2—O4—C2577.1 (3)C16—C17—C18—C19178.5 (4)
Pd1—Pd2—O4—C257.8 (2)C14—N2—C18—C170.1 (5)
C11—Pd1—N1—C1178.4 (3)Pd2—N2—C18—C17178.6 (3)
O1—Pd1—N1—C15.0 (3)C14—N2—C18—C19178.3 (3)
Pd2—Pd1—N1—C172.7 (3)Pd2—N2—C18—C193.3 (4)
C11—Pd1—N1—C54.7 (2)C17—C18—C19—C24176.6 (3)
O1—Pd1—N1—C5178.8 (2)N2—C18—C19—C241.4 (4)
Pd2—Pd1—N1—C5101.1 (2)C17—C18—C19—C204.2 (6)
C24—Pd2—N2—C14176.9 (3)N2—C18—C19—C20177.7 (4)
O3—Pd2—N2—C144.3 (3)C24—C19—C20—C211.3 (7)
Pd1—Pd2—N2—C1489.9 (3)C18—C19—C20—C21179.6 (4)
C24—Pd2—N2—C184.7 (2)C19—C20—C21—C220.6 (8)
O3—Pd2—N2—C18174.0 (2)C20—C21—C22—C231.5 (9)
Pd1—Pd2—N2—C1888.4 (2)C21—C22—C23—C240.5 (8)
C5—N1—C1—C20.1 (5)C22—C23—C24—C191.4 (6)
Pd1—N1—C1—C2173.4 (3)C22—C23—C24—Pd2174.3 (3)
N1—C1—C2—C30.9 (6)C20—C19—C24—C232.3 (5)
C1—C2—C3—C40.5 (6)C18—C19—C24—C23178.6 (3)
C2—C3—C4—C50.5 (5)C20—C19—C24—Pd2173.8 (3)
C1—N1—C5—C40.9 (4)C18—C19—C24—Pd25.4 (4)
Pd1—N1—C5—C4175.0 (2)N2—Pd2—C24—C23178.5 (3)
C1—N1—C5—C6178.5 (3)O4—Pd2—C24—C230.9 (3)
Pd1—N1—C5—C64.4 (3)Pd1—Pd2—C24—C2379.5 (3)
C3—C4—C5—N11.2 (5)N2—Pd2—C24—C195.7 (2)
C3—C4—C5—C6178.1 (3)O4—Pd2—C24—C19174.9 (2)
N1—C5—C6—C7178.9 (3)Pd1—Pd2—C24—C1996.2 (2)
C4—C5—C6—C71.7 (5)Pd2—O4—C25—O26.2 (5)
N1—C5—C6—C111.1 (4)Pd2—O4—C25—C26174.2 (2)
C4—C5—C6—C11178.2 (3)Pd1—O2—C25—O42.2 (5)
C11—C6—C7—C80.8 (5)Pd1—O2—C25—C26177.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O10.932.563.134 (4)120
C23—H23···O40.932.573.146 (4)120
C14—H14···O30.932.543.054 (5)115
C10—H10···O20.932.563.069 (4)115
C7—H7···O3i0.932.563.344 (4)142
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Pd2(C11H8N)2(C2H3O2)2]
Mr639.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.7160 (3), 19.1986 (5), 14.4990 (4)
β (°) 119.451 (2)
V3)2355.06 (12)
Z4
Radiation typeMo Kα
µ (mm1)1.56
Crystal size (mm)0.46 × 0.31 × 0.22
Data collection
DiffractometerStoe IPDSII
diffractometer
Absorption correctionIntegration
(X-RED; Stoe & Cie, 2002)
Tmin, Tmax0.355, 0.728
No. of measured, independent and
observed [I > 2σ(I)] reflections
23605, 5011, 4375
Rint0.136
(sin θ/λ)max1)0.634
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.071, 1.05
No. of reflections5011
No. of parameters309
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—C111.960 (3)Pd2—N21.961 (3)
Pd1—N12.006 (2)Pd2—C242.002 (3)
Pd1—O22.052 (2)Pd2—O32.058 (2)
Pd1—O12.143 (2)Pd2—O42.155 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O10.932.563.134 (4)120
C23—H23···O40.932.573.146 (4)120
C14—H14···O30.932.543.054 (5)115
C10—H10···O20.932.563.069 (4)115
C7—H7···O3i0.932.563.344 (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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