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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m821.
Published online 2008 May 17. doi:  10.1107/S1600536808014141
PMCID: PMC2961565

trans-Di-μ-acetato-κ4 O:O′-bis­[2-(5-phenyl­isoxazolin-3-yl)phenyl-κ2 C 1,N]dipalladium(II)

Abstract

The title compound, [Pd2(C15H10NO)2(C2H3O2)2], crystallized from a dichloro­methane/n-hexane solution with two crystallographically independent dimeric mol­ecules in the asymmetric unit. Each mol­ecule may be described as a dimer with an anti configuration and the cyclo­metallated fragments in the characteristic open-book disposition, linked by two bridging acetate ligands.

Related literature

For a related palladacycle bridged by acetate ligands, see: Schultz et al. (2004 [triangle]). For related literature, see: Dupont et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m821-scheme1.jpg

Experimental

Crystal data

  • [Pd2(C15H10NO)2(C2H3O2)2]
  • M r = 771.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m821-efi1.jpg
  • a = 14.8160 (6) Å
  • b = 24.2339 (10) Å
  • c = 19.6397 (8) Å
  • β = 103.233 (1)°
  • V = 6864.4 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.09 mm−1
  • T = 298 (2) K
  • 0.28 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.750, T max = 0.854
  • 80599 measured reflections
  • 12098 independent reflections
  • 8103 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.143
  • S = 1.09
  • 12098 reflections
  • 793 parameters
  • H-atom parameters constrained
  • Δρmax = 0.81 e Å−3
  • Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]) and PLATON (Spek, 2003 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014141/cf2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014141/cf2190Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by NSFC (No. 20372042), the Doctoral Program of MOE (No. 20050422010 and 20050422011), Shandong Scientific Plan (032090105), and the Science Foundation of Shandong (Y2006B18).

supplementary crystallographic information

Comment

Recently, much attention is being paid to the use of palladacycles as catalyst precursors (Dupont et al., 2005). Palladacycles bridged by acetate ligands have been reported (Schultz et al. 2004). We have prepared a new palladacycle by a C—H bond activation reaction of 3,5-diphenylisoxazole with Pd(OAc)2 in acetic acid. The asymmetric unit contains two molecules of the palladacycle having similar structures, of which only one will be discussed here. The molecular configuration of the complex is a dimeric form of the anti isomer with the cyclopalladated units in an arrangement linked by two acetate bridging ligands between the palladium atoms. The palladium atoms are coordinated in a slightly distorted square-planar arrangement by one cyclometallated isoxazole ligand and two bridging acetate ligands. In the crystal structure, the two cyclopalladated isoxazole subunits of the dimers are arranged in an anti-fashion. The chelating C, N-bonded isoxazoles are forced to lie above one another in the dimeric molecules because Pd1 and Pd2 are bridged by two cis-µ-acetate ligands. The resulting Pd—C (average 1.99 Å) and Pd—N (average 1.98 Å) bond distances fall within the range observed in other palladacycles (Smoliakova et al., 2004). The Pd1···Pd2 distance [2.833 (5) Å] is noticeably larger than the sum of the covalent radii for two square-planar palladium(II) atoms, thus precluding any direct Pd—Pd interaction. The bond lengths of C7—N1 [1.303 (6) Å] and N2—C26 [1.318 (8) Å] are characteristic for C═N double bonds. The Pd—O bond distances trans to the carbon donor are slightly longer (ca 0.13 Å) than those trans to the nitrogen donor, as expected, because of the trans lengthening influence of carbon σ-donors.

Experimental

3,5-Diphenylisoxazole (232 mg, 1.05 mmol) and Pd(OAc)2 (224 mg, 1.0 mmol) were added to 5 ml of acetic acid. The reaction mixture was stirred for 2 h at refluxing temperature. After removing all the volatiles, the orange residue was washed with diethyl ether, and was chromatographed on a silica gel column, eluting with CH2Cl2/n-hexane. The title compound was dried under vacuum, with a yield of 48% (185 mg). Crystals suitable for X-ray diffraction were obtained from the CH2Cl2/n-hexane solution.

Refinement

All H atoms were positioned geometrically and treated as riding on their parent atoms with C—H = 0.93 Å (aromatic), 0.96 (methyl), 0.98 Å (methine), and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C). Highly disordered and unidentified solvent molecules were treated with the SQUEEZE procedure of PLATON (Spek, 2003), as it proved impossible to model them with discrete atoms.

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at 30% probability level.

Crystal data

[Pd2(C15H10NO)2(C2H3O2)2]F000 = 3072
Mr = 771.37Dx = 1.493 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
a = 14.8160 (6) ÅCell parameters from 6715 reflections
b = 24.2339 (10) Åθ = 2.2–24.8º
c = 19.6397 (8) ŵ = 1.09 mm1
β = 103.233 (1)ºT = 298 (2) K
V = 6864.4 (5) Å3Block, yellow
Z = 80.28 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII diffractometer12098 independent reflections
Radiation source: fine-focus sealed tube8103 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −17→17
Tmin = 0.750, Tmax = 0.854k = 0→28
80599 measured reflectionsl = 0→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.143  w = 1/[σ2(Fo2) + (0.0623P)2 + 7.5732P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
12098 reflectionsΔρmax = 0.81 e Å3
793 parametersΔρmin = −0.58 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 (Å2)

xyzUiso*/Ueq
Pd10.25845 (3)0.545234 (17)0.51711 (2)0.06594 (13)
Pd20.22368 (3)0.62048 (2)0.61849 (2)0.08059 (16)
Pd30.27410 (4)0.36805 (3)0.24384 (3)0.1003 (2)
Pd40.11212 (4)0.35074 (3)0.13585 (3)0.1050 (2)
C410.2228 (4)0.4531 (3)0.3289 (3)0.0803 (16)
O60.3757 (2)0.63129 (15)0.46051 (19)0.0714 (9)
C360.2313 (5)0.3043 (4)0.3647 (5)0.107 (2)
H36A0.24580.27190.34420.129*
C70.4499 (3)0.5702 (2)0.5345 (2)0.0617 (12)
O10.1543 (2)0.59872 (17)0.45465 (19)0.0765 (10)
O40.1169 (3)0.5612 (2)0.6166 (2)0.0958 (13)
C10.3602 (3)0.4992 (2)0.5727 (3)0.0652 (12)
O30.1587 (2)0.49888 (17)0.5463 (2)0.0858 (11)
N10.3682 (3)0.58268 (18)0.4966 (2)0.0660 (10)
C80.5150 (3)0.6097 (2)0.5236 (3)0.0709 (14)
H8A0.57820.61040.54360.085*
N20.3127 (3)0.5885 (2)0.6997 (3)0.0857 (14)
C90.4663 (3)0.6461 (2)0.4782 (3)0.0700 (14)
O50.3106 (3)0.5401 (2)0.7351 (2)0.0970 (13)
C170.1105 (4)0.5155 (3)0.5869 (3)0.0850 (17)
O110.0447 (3)0.2742 (2)0.2375 (3)0.0999 (13)
O120.2618 (3)0.4951 (2)0.2398 (2)0.1017 (13)
C190.1241 (4)0.6422 (3)0.4752 (4)0.0794 (16)
C60.4493 (3)0.5203 (2)0.5754 (2)0.0647 (13)
C350.2383 (4)0.3549 (3)0.3329 (3)0.0902 (19)
C40.5163 (4)0.4469 (3)0.6519 (3)0.0861 (17)
H4A0.56790.42960.67950.103*
N30.2566 (4)0.4452 (3)0.2733 (3)0.0996 (16)
O20.1436 (3)0.66146 (18)0.5361 (3)0.0959 (12)
N40.0365 (4)0.3228 (3)0.2003 (3)0.0971 (16)
O80.3198 (4)0.3906 (3)0.1518 (4)0.1283 (19)
C20.3520 (4)0.4515 (2)0.6092 (3)0.0804 (16)
H2A0.29370.43680.60800.096*
C260.3982 (5)0.6078 (3)0.7161 (3)0.0907 (19)
C60−0.0044 (4)0.3596 (3)0.2330 (4)0.0914 (18)
C630.0116 (5)0.2378 (3)0.3431 (4)0.108 (2)
C270.4539 (5)0.5722 (4)0.7614 (4)0.104 (2)
H27A0.51690.57600.78120.125*
O90.1824 (4)0.2750 (2)0.1298 (3)0.1223 (17)
C400.2119 (4)0.4029 (3)0.3649 (3)0.0853 (17)
C200.3298 (4)0.6723 (3)0.6255 (4)0.0850 (17)
O100.2898 (4)0.2855 (2)0.2288 (3)0.1221 (17)
C50.5273 (4)0.4942 (3)0.6153 (3)0.0763 (15)
H5A0.58610.50850.61730.092*
C420.2032 (4)0.5095 (3)0.3326 (3)0.0872 (17)
H42A0.17760.52660.36620.105*
C620.0057 (4)0.2836 (3)0.2939 (4)0.0949 (19)
C430.2283 (4)0.5344 (3)0.2785 (3)0.0872 (17)
C390.1835 (5)0.4005 (3)0.4261 (4)0.104 (2)
H39A0.16750.43270.44640.124*
C100.4897 (4)0.6960 (3)0.4450 (3)0.0874 (17)
C30.4301 (4)0.4254 (3)0.6475 (3)0.0889 (17)
H3A0.42380.39270.67070.107*
C61−0.0257 (4)0.3358 (3)0.2921 (4)0.0950 (19)
H61A−0.05540.35250.32360.114*
C250.4086 (4)0.6570 (3)0.6758 (4)0.094 (2)
C59−0.0077 (5)0.4129 (4)0.2014 (4)0.108 (2)
C440.2302 (4)0.5915 (3)0.2552 (4)0.0955 (19)
C380.1784 (6)0.3490 (4)0.4581 (4)0.116 (2)
H38A0.15890.34670.49980.139*
C210.3336 (5)0.7170 (3)0.5853 (4)0.103 (2)
H21A0.28150.72720.55150.123*
C280.3978 (6)0.5303 (4)0.7713 (4)0.104 (2)
C450.1993 (5)0.6326 (4)0.2909 (4)0.111 (2)
H45A0.17540.62410.32940.134*
C240.4899 (5)0.6874 (4)0.6857 (4)0.113 (2)
H24A0.54240.67730.71930.136*
C110.5732 (5)0.7217 (3)0.4697 (4)0.117 (3)
H11A0.61490.70700.50820.140*
C540.0426 (6)0.4168 (4)0.1491 (4)0.115 (2)
C230.4898 (6)0.7333 (4)0.6437 (6)0.133 (3)
H23A0.54320.75470.65010.159*
C180.0554 (5)0.6765 (3)0.4213 (4)0.117 (2)
H18A0.04470.65870.37650.175*
H18B0.08070.71260.41800.175*
H18C−0.00210.67970.43560.175*
C150.4319 (6)0.7169 (4)0.3868 (5)0.162 (4)
H15A0.37700.69880.36670.194*
C160.0389 (5)0.4753 (4)0.5994 (5)0.128 (3)
H16A0.00500.49140.63060.192*
H16B0.06900.44220.61980.192*
H16C−0.00300.46660.55570.192*
C65−0.0182 (9)0.2019 (5)0.4486 (5)0.151 (4)
H65A−0.04590.20560.48640.181*
C220.4148 (6)0.7481 (3)0.5937 (5)0.120 (3)
H22A0.41720.77860.56540.144*
C64−0.0287 (6)0.2431 (4)0.3992 (5)0.125 (3)
H64A−0.06300.27440.40370.150*
C370.2023 (5)0.3024 (4)0.4275 (5)0.120 (3)
H37A0.19930.26840.44910.143*
C140.4553 (7)0.7657 (5)0.3574 (6)0.201 (6)
H14A0.41470.78090.31870.241*
C460.2028 (7)0.6863 (4)0.2709 (6)0.136 (3)
H46A0.18050.71380.29570.163*
C490.2652 (7)0.6058 (5)0.1991 (5)0.147 (3)
H49A0.28610.57840.17330.176*
C480.2699 (9)0.6601 (6)0.1805 (7)0.179 (5)
H48A0.29560.66930.14300.215*
C58−0.0549 (7)0.4573 (4)0.2205 (6)0.149 (4)
H58A−0.08730.45360.25560.179*
C470.2378 (8)0.7000 (5)0.2160 (6)0.141 (3)
H47A0.23990.73670.20270.169*
C680.0618 (8)0.1913 (4)0.3356 (6)0.154 (4)
H68A0.08690.18660.29670.185*
C550.0464 (8)0.4667 (5)0.1173 (6)0.171 (4)
H55A0.08050.47070.08320.206*
C670.0736 (10)0.1514 (5)0.3883 (8)0.177 (5)
H67A0.11090.12090.38590.212*
C660.0319 (11)0.1563 (5)0.4431 (7)0.176 (5)
H66A0.03790.12840.47630.211*
C120.5961 (6)0.7683 (4)0.4390 (5)0.143 (4)
H12A0.65380.78440.45600.172*
C130.5374 (7)0.7909 (5)0.3852 (6)0.165 (4)
H13A0.55230.82400.36650.198*
C290.4113 (7)0.4800 (4)0.8146 (4)0.117 (3)
C340.3410 (9)0.4440 (5)0.8164 (6)0.156 (4)
H34A0.28190.45140.78960.188*
C330.3558 (12)0.3960 (6)0.8580 (7)0.189 (5)
H33A0.30750.37180.85910.227*
C300.4987 (9)0.4668 (6)0.8520 (7)0.206 (6)
H30A0.54890.48930.85040.247*
C310.5108 (13)0.4185 (10)0.8929 (11)0.277 (12)
H31A0.56960.40910.91870.332*
C57−0.0535 (11)0.5061 (6)0.1877 (7)0.228 (8)
H57A−0.08690.53590.19900.274*
C56−0.0020 (12)0.5119 (5)0.1368 (8)0.247 (8)
H56A0.00050.54600.11560.296*
O70.1818 (5)0.3897 (3)0.0727 (3)0.138 (2)
C510.2666 (8)0.3996 (4)0.0921 (6)0.127 (3)
C530.2457 (7)0.2581 (4)0.1773 (5)0.122 (3)
C520.2749 (8)0.1985 (4)0.1740 (6)0.174 (4)
H52A0.23750.18130.13310.262*
H52B0.26690.17940.21500.262*
H52C0.33890.19700.17180.262*
C500.3113 (9)0.4249 (5)0.0377 (6)0.196 (5)
H50A0.26510.4309−0.00470.294*
H50B0.35810.40040.02860.294*
H50C0.33920.45950.05460.294*
C320.4400 (14)0.3869 (7)0.8950 (8)0.192 (7)
H32A0.45000.35620.92420.230*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pd10.0508 (2)0.0751 (3)0.0743 (3)−0.00960 (18)0.01948 (17)−0.0122 (2)
Pd20.0638 (3)0.0948 (3)0.0854 (3)−0.0040 (2)0.0218 (2)−0.0239 (2)
Pd30.0736 (3)0.1213 (4)0.1066 (4)0.0092 (3)0.0214 (3)−0.0357 (3)
Pd40.0874 (4)0.1304 (5)0.0962 (4)0.0143 (3)0.0189 (3)−0.0161 (3)
C410.059 (3)0.101 (5)0.084 (4)−0.008 (3)0.023 (3)−0.032 (4)
O60.052 (2)0.087 (3)0.077 (2)−0.0084 (17)0.0183 (16)0.0039 (19)
C360.078 (4)0.114 (6)0.110 (6)0.004 (4)−0.021 (4)−0.013 (5)
C70.056 (3)0.074 (3)0.059 (3)0.002 (2)0.021 (2)−0.008 (2)
O10.055 (2)0.091 (3)0.080 (2)−0.0064 (19)0.0069 (17)−0.007 (2)
O40.063 (2)0.129 (4)0.103 (3)−0.019 (2)0.036 (2)−0.012 (3)
C10.061 (3)0.070 (3)0.065 (3)−0.007 (2)0.016 (2)−0.018 (3)
O30.061 (2)0.092 (3)0.108 (3)−0.0222 (19)0.027 (2)−0.009 (2)
N10.055 (2)0.074 (3)0.074 (3)−0.0017 (19)0.024 (2)−0.003 (2)
C80.049 (3)0.091 (4)0.074 (3)−0.007 (3)0.016 (2)−0.002 (3)
N20.079 (3)0.101 (4)0.078 (3)−0.003 (3)0.019 (3)−0.016 (3)
C90.054 (3)0.091 (4)0.069 (3)−0.011 (3)0.022 (2)−0.004 (3)
O50.092 (3)0.119 (4)0.083 (3)0.007 (3)0.026 (2)−0.011 (3)
C170.050 (3)0.116 (5)0.091 (4)−0.024 (3)0.019 (3)0.000 (4)
O110.091 (3)0.099 (3)0.104 (3)0.003 (2)0.011 (3)−0.016 (3)
O120.092 (3)0.118 (4)0.103 (3)−0.009 (3)0.039 (3)−0.024 (3)
C190.050 (3)0.091 (4)0.095 (4)−0.005 (3)0.014 (3)−0.003 (4)
C60.064 (3)0.080 (3)0.054 (3)−0.001 (3)0.021 (2)−0.018 (3)
C350.061 (3)0.109 (5)0.089 (4)0.002 (3)−0.007 (3)−0.025 (4)
C40.077 (4)0.092 (4)0.090 (4)0.016 (3)0.021 (3)0.008 (3)
N30.085 (4)0.106 (4)0.111 (4)−0.009 (3)0.029 (3)−0.027 (4)
O20.078 (3)0.097 (3)0.108 (3)0.006 (2)0.012 (2)−0.020 (3)
N40.079 (3)0.105 (4)0.103 (4)0.011 (3)0.012 (3)−0.011 (4)
O80.102 (4)0.159 (5)0.138 (5)0.007 (3)0.058 (4)−0.041 (4)
C20.077 (4)0.068 (4)0.105 (4)−0.009 (3)0.040 (3)−0.008 (3)
C260.077 (4)0.118 (6)0.076 (4)0.006 (4)0.016 (3)−0.034 (4)
C600.070 (4)0.106 (5)0.090 (5)0.013 (3)0.001 (3)−0.012 (4)
C630.107 (5)0.097 (6)0.114 (6)−0.013 (4)0.016 (4)−0.018 (5)
C270.086 (5)0.137 (7)0.090 (5)0.011 (5)0.018 (4)−0.032 (5)
O90.115 (4)0.133 (4)0.118 (4)0.025 (3)0.024 (3)−0.041 (3)
C400.062 (3)0.111 (5)0.079 (4)−0.006 (3)0.007 (3)−0.024 (4)
C200.080 (4)0.084 (4)0.094 (4)−0.006 (3)0.026 (3)−0.033 (4)
O100.110 (4)0.123 (4)0.124 (4)0.033 (3)0.006 (3)−0.038 (3)
C50.060 (3)0.095 (4)0.075 (3)−0.001 (3)0.017 (3)−0.008 (3)
C420.068 (3)0.112 (5)0.081 (4)−0.003 (3)0.017 (3)−0.018 (4)
C620.073 (4)0.110 (6)0.097 (5)0.001 (4)0.010 (3)−0.014 (4)
C430.064 (3)0.111 (5)0.084 (4)−0.003 (3)0.010 (3)−0.015 (4)
C390.094 (5)0.115 (6)0.097 (5)−0.005 (4)0.012 (4)−0.030 (4)
C100.071 (4)0.104 (5)0.090 (4)−0.015 (3)0.027 (3)0.016 (4)
C30.087 (4)0.084 (4)0.100 (4)0.009 (3)0.030 (4)0.014 (3)
C610.073 (4)0.116 (6)0.096 (5)0.017 (4)0.019 (3)−0.004 (4)
C250.072 (4)0.113 (5)0.100 (5)−0.007 (4)0.025 (4)−0.043 (4)
C590.090 (5)0.125 (6)0.109 (5)0.029 (4)0.023 (4)−0.003 (5)
C440.073 (4)0.117 (6)0.096 (5)−0.004 (4)0.017 (3)0.001 (4)
C380.109 (6)0.135 (7)0.097 (5)−0.009 (5)0.008 (4)0.001 (5)
C210.087 (5)0.105 (5)0.116 (5)−0.006 (4)0.021 (4)−0.028 (5)
C280.112 (6)0.120 (6)0.084 (5)0.033 (5)0.027 (4)−0.018 (4)
C450.113 (6)0.111 (6)0.113 (6)0.001 (5)0.031 (5)0.002 (5)
C240.085 (5)0.137 (7)0.116 (6)−0.021 (5)0.020 (4)−0.043 (5)
C110.074 (4)0.141 (6)0.131 (6)−0.029 (4)0.014 (4)0.033 (5)
C540.106 (5)0.125 (7)0.115 (6)0.027 (5)0.026 (5)0.009 (5)
C230.103 (6)0.143 (8)0.160 (8)−0.045 (6)0.045 (6)−0.052 (7)
C180.092 (5)0.118 (6)0.131 (6)0.014 (4)0.008 (4)0.003 (5)
C150.112 (6)0.201 (10)0.156 (8)−0.061 (6)−0.004 (6)0.094 (8)
C160.079 (4)0.164 (7)0.148 (7)−0.048 (5)0.039 (4)0.003 (6)
C650.202 (11)0.145 (9)0.107 (7)−0.016 (8)0.038 (7)0.003 (7)
C220.124 (7)0.102 (5)0.137 (7)−0.030 (5)0.036 (6)−0.025 (5)
C640.145 (7)0.119 (7)0.108 (6)0.005 (5)0.022 (5)−0.015 (5)
C370.098 (5)0.126 (7)0.114 (6)0.004 (5)−0.018 (5)−0.007 (5)
C140.116 (7)0.268 (14)0.194 (10)−0.071 (8)−0.013 (7)0.138 (10)
C460.138 (8)0.117 (7)0.144 (8)0.010 (6)0.016 (6)0.014 (6)
C490.187 (10)0.140 (8)0.135 (7)0.009 (7)0.080 (7)0.009 (6)
C480.218 (13)0.181 (12)0.157 (10)0.007 (10)0.082 (9)0.050 (9)
C580.167 (9)0.130 (7)0.172 (9)0.056 (6)0.084 (7)0.032 (7)
C470.148 (8)0.134 (8)0.131 (8)−0.005 (7)0.012 (7)0.038 (7)
C680.206 (11)0.101 (6)0.169 (9)0.017 (7)0.073 (8)0.005 (7)
C550.192 (11)0.159 (9)0.194 (11)0.063 (8)0.107 (9)0.041 (8)
C670.242 (14)0.119 (8)0.185 (12)0.017 (8)0.081 (11)0.010 (9)
C660.259 (16)0.112 (8)0.140 (9)0.007 (9)0.010 (10)0.010 (7)
C120.087 (5)0.173 (9)0.167 (8)−0.046 (5)0.025 (5)0.056 (7)
C130.122 (7)0.187 (10)0.189 (10)−0.048 (7)0.040 (7)0.080 (8)
C290.118 (6)0.150 (8)0.090 (5)0.034 (6)0.040 (5)−0.011 (5)
C340.163 (10)0.178 (11)0.130 (8)0.039 (9)0.039 (7)0.017 (8)
C330.232 (16)0.186 (12)0.172 (11)0.064 (11)0.091 (11)0.058 (10)
C300.144 (10)0.238 (14)0.226 (13)0.075 (10)0.024 (9)0.071 (12)
C310.175 (15)0.35 (3)0.31 (2)0.122 (17)0.063 (15)0.17 (2)
C570.325 (18)0.177 (11)0.244 (14)0.130 (12)0.192 (14)0.082 (11)
C560.339 (19)0.170 (11)0.296 (17)0.126 (13)0.206 (17)0.117 (12)
O70.114 (4)0.193 (6)0.114 (4)0.019 (4)0.040 (4)−0.004 (4)
C510.134 (8)0.141 (7)0.124 (7)0.021 (6)0.065 (7)−0.018 (6)
C530.118 (6)0.135 (7)0.116 (6)0.031 (6)0.030 (5)−0.032 (6)
C520.214 (11)0.130 (8)0.180 (10)0.058 (8)0.046 (9)−0.035 (7)
C500.227 (13)0.232 (13)0.165 (9)0.017 (10)0.120 (10)0.014 (9)
C320.243 (18)0.196 (14)0.157 (10)0.124 (14)0.087 (13)0.055 (10)

Geometric parameters (Å, °)

Pd1—N11.983 (4)C61—H61A0.930
Pd1—C11.989 (5)C25—C241.386 (10)
Pd1—O32.041 (4)C59—C581.382 (11)
Pd1—O12.168 (4)C59—C541.404 (10)
Pd2—N21.980 (5)C44—C451.355 (10)
Pd2—C201.992 (6)C44—C491.365 (11)
Pd2—O22.033 (5)C38—C371.364 (11)
Pd2—O42.131 (4)C38—H38A0.930
Pd3—C351.966 (7)C21—C221.397 (10)
Pd3—N31.991 (6)C21—H21A0.930
Pd3—O102.044 (5)C28—C291.475 (12)
Pd3—O82.141 (6)C45—C461.363 (11)
Pd4—C541.954 (8)C45—H45A0.930
Pd4—N41.990 (6)C24—C231.385 (12)
Pd4—O72.021 (6)C24—H24A0.930
Pd4—O92.128 (5)C11—C121.360 (10)
C41—N31.315 (8)C11—H11A0.930
C41—C421.404 (9)C54—C551.368 (12)
C41—C401.434 (9)C23—C221.352 (12)
O6—C91.355 (6)C23—H23A0.930
O6—N11.392 (5)C18—H18A0.960
C36—C351.391 (10)C18—H18B0.960
C36—C371.397 (11)C18—H18C0.960
C36—H36A0.930C15—C141.392 (12)
C7—N11.303 (6)C15—H15A0.930
C7—C81.408 (7)C16—H16A0.960
C7—C61.454 (7)C16—H16B0.960
O1—C191.247 (7)C16—H16C0.960
O4—C171.245 (8)C65—C661.351 (15)
C1—C21.380 (8)C65—C641.375 (12)
C1—C61.406 (7)C65—H65A0.930
O3—C171.251 (7)C22—H22A0.930
C8—C91.340 (7)C64—H64A0.930
C8—H8A0.930C37—H37A0.930
N2—C261.318 (8)C14—C131.360 (13)
N2—O51.368 (7)C14—H14A0.930
C9—C101.454 (8)C46—C471.341 (13)
O5—C281.345 (8)C46—H46A0.930
C17—C161.502 (8)C49—C481.371 (15)
O11—N41.376 (7)C49—H49A0.930
O11—C621.381 (8)C48—C471.341 (14)
O12—C431.380 (7)C48—H48A0.930
O12—N31.389 (7)C58—C571.348 (13)
C19—O21.254 (7)C58—H58A0.930
C19—C181.535 (9)C47—H47A0.930
C6—C51.390 (7)C68—C671.397 (14)
C35—C401.418 (9)C68—H68A0.930
C4—C31.364 (8)C55—C561.410 (14)
C4—C51.383 (8)C55—H55A0.930
C4—H4A0.930C67—C661.364 (16)
N4—C601.325 (8)C67—H67A0.930
O8—C511.273 (11)C66—H66A0.930
C2—C31.379 (8)C12—C131.324 (12)
C2—H2A0.930C12—H12A0.930
C26—C271.372 (10)C13—H13A0.930
C26—C251.460 (10)C29—C341.363 (13)
C60—C611.396 (9)C29—C301.372 (13)
C60—C591.428 (10)C34—C331.409 (15)
C63—C641.373 (11)C34—H34A0.930
C63—C681.377 (11)C33—C321.312 (18)
C63—C621.460 (11)C33—H33A0.930
C27—C281.354 (11)C30—C311.41 (2)
C27—H27A0.930C30—H30A0.930
O9—C531.231 (9)C31—C321.31 (2)
C40—C391.363 (9)C31—H31A0.930
C20—C211.349 (10)C57—C561.398 (15)
C20—C251.396 (9)C57—H57A0.930
O10—C531.260 (9)C56—H56A0.930
C5—H5A0.930O7—C511.250 (11)
C42—C431.347 (9)C51—C501.511 (13)
C42—H42A0.930C53—C521.513 (12)
C62—C611.347 (9)C52—H52A0.960
C43—C441.460 (10)C52—H52B0.960
C39—C381.409 (11)C52—H52C0.960
C39—H39A0.930C50—H50A0.960
C10—C151.360 (10)C50—H50B0.960
C10—C111.370 (9)C50—H50C0.960
C3—H3A0.930C32—H32A0.930
N1—Pd1—C179.3 (2)C45—C44—C43120.1 (7)
N1—Pd1—O3171.81 (17)C49—C44—C43122.0 (8)
C1—Pd1—O392.49 (19)C37—C38—C39119.5 (8)
N1—Pd1—O197.02 (16)C37—C38—H38A120.3
C1—Pd1—O1176.35 (18)C39—C38—H38A120.3
O3—Pd1—O191.16 (15)C20—C21—C22121.0 (8)
N2—Pd2—C2079.7 (3)C20—C21—H21A119.5
N2—Pd2—O2172.7 (2)C22—C21—H21A119.5
C20—Pd2—O293.1 (3)O5—C28—C27109.8 (7)
N2—Pd2—O496.0 (2)O5—C28—C29116.0 (8)
C20—Pd2—O4175.7 (3)C27—C28—C29134.1 (9)
O2—Pd2—O491.14 (18)C44—C45—C46120.8 (9)
C35—Pd3—N379.3 (3)C44—C45—H45A119.6
C35—Pd3—O1091.8 (3)C46—C45—H45A119.6
N3—Pd3—O10171.0 (3)C23—C24—C25117.4 (8)
C35—Pd3—O8173.7 (3)C23—C24—H24A121.3
N3—Pd3—O895.3 (2)C25—C24—H24A121.3
O10—Pd3—O893.5 (2)C12—C11—C10121.1 (7)
C54—Pd4—N478.7 (3)C12—C11—H11A119.4
C54—Pd4—O793.3 (3)C10—C11—H11A119.4
N4—Pd4—O7171.9 (3)C55—C54—C59118.7 (8)
C54—Pd4—O9174.1 (3)C55—C54—Pd4125.8 (7)
N4—Pd4—O995.5 (2)C59—C54—Pd4115.2 (6)
O7—Pd4—O992.5 (2)C22—C23—C24122.3 (8)
N3—C41—C42107.9 (6)C22—C23—H23A118.8
N3—C41—C40113.1 (6)C24—C23—H23A118.8
C42—C41—C40138.9 (6)C19—C18—H18A109.5
C9—O6—N1106.4 (4)C19—C18—H18B109.5
C35—C36—C37119.7 (8)H18A—C18—H18B109.5
C35—C36—H36A120.1C19—C18—H18C109.5
C37—C36—H36A120.1H18A—C18—H18C109.5
N1—C7—C8109.5 (5)H18B—C18—H18C109.5
N1—C7—C6112.7 (4)C10—C15—C14119.8 (8)
C8—C7—C6137.8 (5)C10—C15—H15A120.1
C19—O1—Pd1125.7 (4)C14—C15—H15A120.1
C17—O4—Pd2125.8 (4)C17—C16—H16A109.5
C2—C1—C6118.6 (5)C17—C16—H16B109.5
C2—C1—Pd1127.6 (4)H16A—C16—H16B109.5
C6—C1—Pd1113.8 (4)C17—C16—H16C109.5
C17—O3—Pd1123.9 (4)H16A—C16—H16C109.5
C7—N1—O6108.3 (4)H16B—C16—H16C109.5
C7—N1—Pd1118.4 (4)C66—C65—C64120.8 (11)
O6—N1—Pd1131.0 (3)C66—C65—H65A119.6
C9—C8—C7105.4 (5)C64—C65—H65A119.6
C9—C8—H8A127.3C23—C22—C21119.0 (9)
C7—C8—H8A127.3C23—C22—H22A120.5
C26—N2—O5108.1 (6)C21—C22—H22A120.5
C26—N2—Pd2118.9 (5)C63—C64—C65120.0 (9)
O5—N2—Pd2131.0 (4)C63—C64—H64A120.0
C8—C9—O6110.3 (5)C65—C64—H64A120.0
C8—C9—C10134.3 (5)C38—C37—C36121.7 (9)
O6—C9—C10115.4 (5)C38—C37—H37A119.2
C28—O5—N2106.8 (6)C36—C37—H37A119.2
O4—C17—O3126.2 (5)C13—C14—C15120.0 (9)
O4—C17—C16118.8 (6)C13—C14—H14A120.0
O3—C17—C16115.0 (7)C15—C14—H14A120.0
N4—O11—C62106.5 (5)C47—C46—C45121.0 (10)
C43—O12—N3105.9 (5)C47—C46—H46A119.5
O1—C19—O2127.0 (6)C45—C46—H46A119.5
O1—C19—C18117.7 (6)C44—C49—C48120.6 (10)
O2—C19—C18115.3 (6)C44—C49—H49A119.7
C5—C6—C1120.6 (5)C48—C49—H49A119.7
C5—C6—C7125.4 (5)C47—C48—C49120.6 (11)
C1—C6—C7114.0 (5)C47—C48—H48A119.7
C36—C35—C40117.8 (7)C49—C48—H48A119.7
C36—C35—Pd3127.3 (6)C57—C58—C59119.3 (9)
C40—C35—Pd3114.7 (6)C57—C58—H58A120.3
C3—C4—C5120.2 (6)C59—C58—H58A120.3
C3—C4—H4A119.9C48—C47—C46119.1 (11)
C5—C4—H4A119.9C48—C47—H47A120.4
C41—N3—O12109.9 (5)C46—C47—H47A120.4
C41—N3—Pd3118.5 (5)C63—C68—C67117.8 (10)
O12—N3—Pd3130.9 (4)C63—C68—H68A121.1
C19—O2—Pd2122.8 (4)C67—C68—H68A121.1
C60—N4—O11108.2 (6)C54—C55—C56119.0 (10)
C60—N4—Pd4117.7 (5)C54—C55—H55A120.5
O11—N4—Pd4129.4 (4)C56—C55—H55A120.5
C51—O8—Pd3124.9 (6)C66—C67—C68121.5 (12)
C3—C2—C1120.3 (5)C66—C67—H67A119.2
C3—C2—H2A119.9C68—C67—H67A119.2
C1—C2—H2A119.9C65—C66—C67119.4 (12)
N2—C26—C27109.8 (7)C65—C66—H66A120.3
N2—C26—C25111.8 (6)C67—C66—H66A120.3
C27—C26—C25138.0 (7)C13—C12—C11120.9 (8)
N4—C60—C61109.9 (7)C13—C12—H12A119.6
N4—C60—C59111.9 (7)C11—C12—H12A119.6
C61—C60—C59138.0 (7)C12—C13—C14119.8 (9)
C64—C63—C68120.4 (9)C12—C13—H13A120.1
C64—C63—C62119.3 (8)C14—C13—H13A120.1
C68—C63—C62120.2 (9)C34—C29—C30118.0 (11)
C28—C27—C26105.4 (7)C34—C29—C28122.7 (9)
C28—C27—H27A127.3C30—C29—C28119.2 (11)
C26—C27—H27A127.3C29—C34—C33121.6 (13)
C53—O9—Pd4122.8 (5)C29—C34—H34A119.2
C39—C40—C35121.9 (7)C33—C34—H34A119.2
C39—C40—C41124.1 (7)C32—C33—C34117.5 (16)
C35—C40—C41113.8 (6)C32—C33—H33A121.2
C21—C20—C25119.1 (6)C34—C33—H33A121.2
C21—C20—Pd2127.1 (5)C29—C30—C31118.8 (15)
C25—C20—Pd2113.6 (6)C29—C30—H30A120.6
C53—O10—Pd3125.2 (5)C31—C30—H30A120.6
C4—C5—C6119.2 (5)C32—C31—C30120.4 (16)
C4—C5—H5A120.4C32—C31—H31A119.8
C6—C5—H5A120.4C30—C31—H31A119.8
C43—C42—C41107.3 (6)C58—C57—C56120.0 (10)
C43—C42—H42A126.4C58—C57—H57A120.0
C41—C42—H42A126.4C56—C57—H57A120.0
C61—C62—O11109.8 (7)C57—C56—C55120.8 (11)
C61—C62—C63134.4 (7)C57—C56—H56A119.6
O11—C62—C63115.7 (7)C55—C56—H56A119.6
C42—C43—O12109.0 (6)C51—O7—Pd4121.4 (6)
C42—C43—C44134.4 (7)O7—C51—O8128.1 (9)
O12—C43—C44116.5 (6)O7—C51—C50115.8 (10)
C40—C39—C38119.3 (7)O8—C51—C50116.2 (10)
C40—C39—H39A120.4O9—C53—O10126.7 (8)
C38—C39—H39A120.4O9—C53—C52117.4 (9)
C15—C10—C11118.2 (6)O10—C53—C52115.8 (9)
C15—C10—C9121.3 (6)C53—C52—H52A109.5
C11—C10—C9120.5 (6)C53—C52—H52B109.5
C4—C3—C2121.1 (6)H52A—C52—H52B109.5
C4—C3—H3A119.5C53—C52—H52C109.5
C2—C3—H3A119.5H52A—C52—H52C109.5
C62—C61—C60105.6 (6)H52B—C52—H52C109.5
C62—C61—H61A127.2C51—C50—H50A109.5
C60—C61—H61A127.2C51—C50—H50B109.5
C24—C25—C20121.2 (8)H50A—C50—H50B109.5
C24—C25—C26123.7 (8)C51—C50—H50C109.5
C20—C25—C26115.2 (6)H50A—C50—H50C109.5
C58—C59—C54122.1 (9)H50B—C50—H50C109.5
C58—C59—C60123.8 (8)C31—C32—C33123.5 (17)
C54—C59—C60114.1 (7)C31—C32—H32A118.2
C45—C44—C49117.8 (8)C33—C32—H32A118.2

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CF2190).

References

  • Bruker (1997). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2005). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dupont, J., Consorti, C. S. & Spencer, J. (2005). Chem. Rev.105, 2527–2571. [PubMed]
  • Schultz, T., Schmees, N. & Pfaltz, A. (2004). Appl. Organomet. Chem.18, 595–601.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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