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Acta Cryst. (2009). E65, m1166    [ doi:10.1107/S1600536809035272 ]

Dichlorido(4,5-diazafluoren-9-one-[kappa]2N,N')palladium(II)

Z.-G. Xu, H.-Y. Liu, Q.-G. Zhan, J. Chen and M.-J. Xu

Abstract top

The structure of the title compound, [PdCl2(C11H6N2O)], shows a nearly square-planar geometry for the PdII atom within a Cl2N2 donor set.

Comment top

The title compound, (I), Fig. 1, shows the palladium atom to be coordinated by two chlorides and two nitrogen atoms, the latter derived from a chelating 4,5-diazafluoren-9-one (dafo) ligand. The coordination geometry is based on a square planar arrangement of the four donor atoms. Related palladium structures featuring dafo ligands are known (Klein et al., 1998).

Related literature top

For related palladium complexes see: Klein et al., (1998).

Experimental top

Compound (I) was synthesized hydrothermally from an aqueous mixture (10.0 ml) containing PdCl2 (0.1758 g) and 4,5-diazafluoren-9-one (0.301 g) in a 30 ml Teflon-lined stainless steel vessel. In the vessel, the solution was heated to 413 K for 72 h then cooled to room temperature at a rate of 10 K per hour. Brown prisms were obtained after washed thoroughly with deionized water and air-drying.

Refinement top

All H atoms were refined: range of C-H = 0.89 (3) to 0.99 (4) Å.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.
Dichlorido(4,5-diazafluoren-9-one-κ2N,N')palladium(II) top
Crystal data top
[PdCl2(C11H6N2O)]F(000) = 696
Mr = 359.48Dx = 2.159 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 13853 reflections
a = 5.131 (5) Åθ = 1.8–28.2°
b = 17.105 (5) ŵ = 2.14 mm−1
c = 12.763 (5) ÅT = 293 K
β = 99.183 (5)°Block, yellow
V = 1105.8 (12) Å30.35 × 0.33 × 0.25 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		2703 independent reflections
Radiation source: fine-focus sealed tube2198 reflections with I > 2σ(I)
graphiteRint = 0.028
Detector resolution: 10 pixels mm-1θmax = 28.4°, θmin = 2.0°
ω scansh = −6→6
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −22→13
Tmin = 0.477, Tmax = 0.586l = −16→16
6785 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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0199P)2 + 0.6053P]
where P = (Fo2 + 2Fc2)/3
2703 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.54 e Å−3
Crystal data top
[PdCl2(C11H6N2O)]V = 1105.8 (12) Å3
Mr = 359.48Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.131 (5) ŵ = 2.14 mm−1
b = 17.105 (5) ÅT = 293 K
c = 12.763 (5) Å0.35 × 0.33 × 0.25 mm
β = 99.183 (5)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		2703 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2198 reflections with I > 2σ(I)
Tmin = 0.477, Tmax = 0.586Rint = 0.028
6785 measured reflectionsθmax = 28.4°
Refinement top
R[F2 > 2σ(F2)] = 0.029All H-atom parameters refined
wR(F2) = 0.058Δρmax = 0.37 e Å−3
S = 1.04Δρmin = −0.54 e Å−3
2703 reflectionsAbsolute structure: ?
178 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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 Rfactors(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
Pd10.08571 (4)0.152850 (13)0.283179 (18)0.03075 (8)
N20.2819 (5)0.16090 (14)0.15176 (19)0.0336 (6)
N10.2865 (4)0.04745 (13)0.30833 (19)0.0303 (5)
C60.6231 (5)0.08217 (18)0.0892 (2)0.0343 (7)
C40.6221 (6)−0.01682 (17)0.2253 (2)0.0322 (6)
C50.7568 (6)0.00609 (19)0.1320 (2)0.0378 (7)
O10.9357 (5)−0.02803 (14)0.10159 (19)0.0532 (6)
C110.4449 (5)0.04170 (17)0.2364 (2)0.0319 (6)
C100.4439 (5)0.10020 (17)0.1557 (2)0.0317 (6)
C30.6398 (6)−0.0784 (2)0.2962 (3)0.0402 (8)
C80.4677 (7)0.1976 (2)−0.0016 (3)0.0434 (8)
C10.3028 (6)−0.01242 (19)0.3780 (3)0.0367 (7)
C90.2942 (6)0.2103 (2)0.0695 (3)0.0397 (7)
C70.6379 (7)0.1337 (2)0.0064 (3)0.0414 (8)
C20.4742 (6)−0.0747 (2)0.3724 (3)0.0413 (8)
Cl1−0.10542 (16)0.13410 (5)0.42956 (7)0.0445 (2)
Cl2−0.11747 (16)0.26981 (5)0.24949 (7)0.0479 (2)
H10.187 (6)−0.0098 (17)0.429 (2)0.038 (9)*
H30.762 (7)−0.123 (2)0.295 (3)0.052 (10)*
H40.753 (6)0.1289 (19)−0.038 (3)0.048 (10)*
H20.477 (6)−0.115 (2)0.420 (3)0.046 (9)*
H50.465 (6)0.2338 (19)−0.055 (3)0.043 (9)*
H60.181 (6)0.2543 (19)0.064 (2)0.046 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.02879 (12)0.02863 (13)0.03619 (14)−0.00123 (9)0.00940 (9)−0.00117 (10)
N20.0321 (13)0.0332 (14)0.0364 (14)−0.0019 (11)0.0084 (10)0.0016 (11)
N10.0293 (12)0.0303 (13)0.0328 (14)−0.0010 (10)0.0097 (10)0.0015 (10)
C60.0300 (15)0.0392 (18)0.0341 (17)−0.0042 (13)0.0070 (12)−0.0008 (13)
C40.0306 (15)0.0341 (16)0.0330 (17)−0.0017 (12)0.0086 (12)−0.0034 (13)
C50.0351 (16)0.0419 (18)0.0373 (18)−0.0013 (14)0.0093 (14)−0.0042 (14)
O10.0540 (14)0.0596 (16)0.0516 (15)0.0154 (12)0.0258 (12)0.0029 (12)
C110.0281 (15)0.0337 (16)0.0340 (17)−0.0032 (12)0.0056 (12)−0.0019 (12)
C100.0279 (14)0.0343 (17)0.0329 (16)−0.0027 (12)0.0049 (12)0.0010 (13)
C30.0390 (18)0.0366 (18)0.046 (2)0.0071 (14)0.0092 (15)0.0012 (15)
C80.051 (2)0.045 (2)0.0340 (19)−0.0075 (16)0.0075 (15)0.0118 (15)
C10.0366 (17)0.0387 (18)0.0366 (18)−0.0027 (14)0.0112 (14)0.0016 (14)
C90.0401 (18)0.0362 (18)0.043 (2)0.0004 (15)0.0070 (14)0.0079 (14)
C70.0427 (19)0.049 (2)0.0345 (19)−0.0075 (15)0.0114 (15)−0.0019 (15)
C20.0461 (19)0.0348 (18)0.044 (2)0.0026 (15)0.0122 (15)0.0084 (15)
Cl10.0490 (5)0.0435 (5)0.0461 (5)−0.0033 (4)0.0235 (4)−0.0035 (4)
Cl20.0470 (5)0.0334 (4)0.0651 (6)0.0065 (4)0.0147 (4)0.0033 (4)
Geometric parameters (Å, °) top
Pd1—N12.076 (2)C4—C51.521 (4)
Pd1—N22.094 (3)C5—O11.203 (4)
Pd1—Cl22.2652 (11)C11—C101.436 (4)
Pd1—Cl12.2672 (12)C3—C21.391 (5)
N2—C101.326 (4)C8—C91.387 (5)
N2—C91.356 (4)C8—C71.392 (5)
N1—C111.323 (4)C1—C21.390 (5)
N1—C11.350 (4)H3—C30.99 (4)
C6—C101.382 (4)H1—C10.95 (3)
C6—C71.387 (4)H2—C20.92 (4)
C6—C51.531 (4)H5—C80.92 (4)
C4—C111.375 (4)H6—C90.95 (3)
C4—C31.382 (4)H4—C70.89 (3)
N1—Pd1—N283.74 (10)C4—C11—C10111.1 (3)
N1—Pd1—Cl2176.78 (7)N2—C10—C6128.8 (3)
N2—Pd1—Cl293.17 (8)N2—C10—C11120.2 (3)
N1—Pd1—Cl191.09 (7)C6—C10—C11111.0 (3)
N2—Pd1—Cl1174.80 (7)C4—C3—C2116.1 (3)
Cl2—Pd1—Cl192.00 (4)C9—C8—C7122.3 (3)
C10—N2—C9114.2 (3)N1—C1—C2121.3 (3)
C10—N2—Pd1107.26 (19)N2—C9—C8121.6 (3)
C9—N2—Pd1138.5 (2)C6—C7—C8116.4 (3)
C11—N1—C1114.8 (3)C1—C2—C3122.2 (3)
C11—N1—Pd1107.58 (19)C7—C8—H5121.(2)
C1—N1—Pd1137.5 (2)C9—C8—H5116.(2)
C10—C6—C7116.7 (3)N1—C1—H1115.8 (18)
C10—C6—C5106.0 (3)C2—C1—H1122.8 (18)
C7—C6—C5137.4 (3)C1—C2—H2119.(2)
C11—C4—C3117.6 (3)C3—C2—H2119.(2)
C11—C4—C5106.5 (3)N2—C9—H6116.7 (17)
C3—C4—C5135.9 (3)C8—C9—H6121.8 (17)
O1—C5—C4126.4 (3)C4—C3—H3124.(2)
O1—C5—C6128.2 (3)C2—C3—H3120.(2)
C4—C5—C6105.3 (2)C6—C7—H4124.(2)
N1—C11—C4128.0 (3)C8—C7—H4120.(2)
N1—C11—C10120.9 (3)
Acknowledgements top

This work was supported by the Natural Science Foundation of Guangdong Province (No. 8451063101000730). The authors thank Professor Zhong Min Su and Dr Kui Zhan Shao (Northeast Normal University) for their assistance with the X-ray crystallographic analysis.

references
References top

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Klein, R. A., Witte, P., van Belzen, R., Fraanje, J., Goubitz, K., Numan, M., Schenk, H., Ernsting, J. M. & Elsevier, C. J. (1998). Eur. J. Inorg. Chem. pp. 319–330.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.