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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page m1022
https://doi.org/10.1107/S1600536810028916

Bis{1-[(E)-(2-methyl­phen­yl)diazen­yl]-2-naphtho­lato}palladium(II)

Meng-Ling Lin,a Chen-Yen Tsai,a Chen-Yu Li,a Bor-Hunn Huangb and Bao-Tsan Koa*

aDepartment of Chemistry, Chung Yuan Christian University, Chung-Li 320, Taiwan, and bR&D department, Min Chung Technology, Hsinchu City 300, Taiwan
*Correspondence e-mail: btko@cycu.edu.tw

(Received 10 July 2010; accepted 20 July 2010; online 24 July 2010)

In the title compound, [Pd(C17H13N2O)2], the PdII atom is tetra­coordinated by two N atoms and two O atoms from two bidentate methylphenyl­diazenylnaphtolate ligands, forming a square-planar complex. The two N atoms and two O atoms around the PdII atom are trans to each other (as the PdII atom lies on a crystallographic inversion centre) with O—Pd—N bond angles of 89.60 (11) and 90.40 (11)°. The distances between the PdII atom and the coordinated O and N atoms are 1.966 (3) and 2.009 (3) Å, respectively.

Related literature

For the Suzuki cross-coupling reactions of palladium complexes with N,O-bidentate ligands or imine–phenol ligands, see: Lai et al. (2005[Lai, Y.-C., Chen, H.-Y., Hung, W.-C., Lin, C.-C. & Hong, F.-E. (2005). Tetrahedron, 61, 9484-9489.]). For the synthesis and characterization of a bis­(phen­oxy­ketimine) Pd(II) complex, see: Brayton et al. (2009[Brayton, D. F., Larkin, T. M., Vicic, D. A. & Navarro, O. (2009). J. Organomet. Chem. 576, 3008-3011.]). For a related structure: see: Tsai et al. (2009[Tsai, C.-Y., Lin, C.-H. & Ko, B.-T. (2009). Acta Cryst. E65, m619.]).

[Scheme 1]

Experimental

Crystal data

  • [Pd(C17H13N2O)2]

  • Mr = 628.99

  • Monoclinic, C 2/c

  • a = 22.9997 (7) Å

  • b = 4.8374 (2) Å

  • c = 24.7294 (7) Å

  • β = 94.151 (2)°

  • V = 2744.15 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.72 mm−1

  • T = 296 K

  • 0.53 × 0.28 × 0.15 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.783, Tmax = 0.900

  • 12830 measured reflections

  • 3412 independent reflections

  • 2463 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.091

  • S = 1.01

  • 3412 reflections

  • 187 parameters

  • H-atom parameters constrained

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810028916/nk2047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028916/nk2047Isup2.hkl

checkCIF report


Comment top

1-Phenylazo-2-naphtol (PAN-H) derivatives are widely used as an orange-red appearance for the additive of colour waxes, oil, petrol, solvents and polishes. In term of coordination chemistry, the phenylazo-naphtolate group can provide N,O-bidentate chelation to stabilize the transition metal or main group metal complexes. Recently, Lai et al. (2005) reported the palladium complexes supported by N,O-bidentate ligands and the imine-phenol ligands in the presence of Pd(OAc)2 have been demonstrated effectively to catalyze Suzuki cross-coupling reactions. Most recently, the air- and moisture-stable bis(phenoxyketimine) Pd(II) complex has been synthesized and characterized (Brayton et al., 2009). In addition, its activity as the precatalyst in the Suzuki–Miyaura crosscoupling reaction has been studied, and it catalyzes the coupling of unactivated aryl bromides with boronic acids in good yields under mild temperature and short reaction time. Therefore, our group is interested in the synthesis and preparation of palladium complexes derived from N, O-bidentate ligands. For example, our group has successfully synthesized and structural characterized the Pd complex (II) with 4-methyl-2-(2H-benzotriazol-2-yl)-phenolate ligands (Tsai et al., 2009). We report herein the synthesis and crystal structure of N, O-bidentate phenylazo-naphtolate ligands incorporated PdII complex (I), a potential catalyst for palladium-catalyzed Suzuki cross-coupling reactions (Scheme 1).

The solid structure of (I) reveals a monomeric PdII complex (Fig. 1) containing two six-membered rings coordinated from these two N, O-bidentate phenylazo-naphtolate ligands. It was found that the asymmetric unit has one half of molecule in which the Pd atom lies on a centre of symmetry. The geometry around Pd atom is tetra-coordinated with a normal square planar environment in which two nitrogen atoms and two oxygen atoms are coplanar. The two N atoms and two O atoms around Pd atom are trans to each other with an O—Pd—N2 bond angle of 89.60 (11)° and O—Pd—N2i of 90.40 (11)°. The distances between the Pd atom and O and N2 are 1.966 (3) Å, 2.009 (3) Å, respectively. These bond distances and angles are similar to those found in the crystal structure of bis[4-methyl-2-(2H-benzotriazol-2-yl)phenolato]Palladium (II) (Tsai et al., 2009).

Related literature top

For the Suzuki cross-coupling reactions of palladium complexes with N,O-bidentate ligands or imine–phenol ligands, see: Lai et al. (2005). For the synthesis and characterization of a bis(phenoxyketimine) Pd(II) complex, see: Brayton et al. (2009). For a related structure: see: Tsai et al. (2009).

Experimental top

The title compound (I) was synthesized by the following procedures:

(E)-1-(o-tolyldiazenyl)naphthalen-2-ol (0.52 g, 2.0 mmol) and Pd(OAc)2 (0.22 g, 1.0 mmol) was stirred at 298 K in THF (25 ml) for 24 h. Volatile materials were removed under vacuum and the residue was washed twice from hexane solution to give dark purple solids. The resulting solids were crystallized from CH2Cl2/Hexane (1:5) solution to yield purple crystals.

Refinement top

The H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C–H = 0.93 Å with Uiso(H) = 1.2 Ueq(C) for phenyl hydrogen; 0.96 Å with Uiso(H) = 1.5 Ueq(C) for CH3 group.

Structure description top

1-Phenylazo-2-naphtol (PAN-H) derivatives are widely used as an orange-red appearance for the additive of colour waxes, oil, petrol, solvents and polishes. In term of coordination chemistry, the phenylazo-naphtolate group can provide N,O-bidentate chelation to stabilize the transition metal or main group metal complexes. Recently, Lai et al. (2005) reported the palladium complexes supported by N,O-bidentate ligands and the imine-phenol ligands in the presence of Pd(OAc)2 have been demonstrated effectively to catalyze Suzuki cross-coupling reactions. Most recently, the air- and moisture-stable bis(phenoxyketimine) Pd(II) complex has been synthesized and characterized (Brayton et al., 2009). In addition, its activity as the precatalyst in the Suzuki–Miyaura crosscoupling reaction has been studied, and it catalyzes the coupling of unactivated aryl bromides with boronic acids in good yields under mild temperature and short reaction time. Therefore, our group is interested in the synthesis and preparation of palladium complexes derived from N, O-bidentate ligands. For example, our group has successfully synthesized and structural characterized the Pd complex (II) with 4-methyl-2-(2H-benzotriazol-2-yl)-phenolate ligands (Tsai et al., 2009). We report herein the synthesis and crystal structure of N, O-bidentate phenylazo-naphtolate ligands incorporated PdII complex (I), a potential catalyst for palladium-catalyzed Suzuki cross-coupling reactions (Scheme 1).

The solid structure of (I) reveals a monomeric PdII complex (Fig. 1) containing two six-membered rings coordinated from these two N, O-bidentate phenylazo-naphtolate ligands. It was found that the asymmetric unit has one half of molecule in which the Pd atom lies on a centre of symmetry. The geometry around Pd atom is tetra-coordinated with a normal square planar environment in which two nitrogen atoms and two oxygen atoms are coplanar. The two N atoms and two O atoms around Pd atom are trans to each other with an O—Pd—N2 bond angle of 89.60 (11)° and O—Pd—N2i of 90.40 (11)°. The distances between the Pd atom and O and N2 are 1.966 (3) Å, 2.009 (3) Å, respectively. These bond distances and angles are similar to those found in the crystal structure of bis[4-methyl-2-(2H-benzotriazol-2-yl)phenolato]Palladium (II) (Tsai et al., 2009).

For the Suzuki cross-coupling reactions of palladium complexes with N,O-bidentate ligands or imine–phenol ligands, see: Lai et al. (2005). For the synthesis and characterization of a bis(phenoxyketimine) Pd(II) complex, see: Brayton et al. (2009). For a related structure: see: Tsai et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the I with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry operator: i, -x+1/2, -y+3/2, -z+2.
Bis{1-[(E)-(2-methylphenyl)diazenyl]-2-naphtholato}palladium(II) top
Crystal data top
[Pd(C17H13N2O)2]F(000) = 1280
Mr = 628.99Dx = 1.522 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7356 reflections
a = 22.9997 (7) Åθ = 2.3–28.2°
b = 4.8374 (2) ŵ = 0.72 mm−1
c = 24.7294 (7) ÅT = 296 K
β = 94.151 (2)°Block, purple
V = 2744.15 (16) Å30.53 × 0.28 × 0.15 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		3412 independent reflections
Radiation source: fine-focus sealed tube2463 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 8.3333 pixels mm-1θmax = 28.3°, θmin = 1.7°
φ and ω scansh = −29→30
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		k = −6→6
Tmin = 0.783, Tmax = 0.900l = −32→32
12830 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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0308P)2 + 8.4214P]
where P = (Fo2 + 2Fc2)/3
3412 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.57 e Å−3
0 restraintsΔρmin = −0.39 e Å−3
Crystal data top
[Pd(C17H13N2O)2]V = 2744.15 (16) Å3
Mr = 628.99Z = 4
Monoclinic, C2/cMo Kα radiation
a = 22.9997 (7) ŵ = 0.72 mm−1
b = 4.8374 (2) ÅT = 296 K
c = 24.7294 (7) Å0.53 × 0.28 × 0.15 mm
β = 94.151 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		3412 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		2463 reflections with I > 2σ(I)
Tmin = 0.783, Tmax = 0.900Rint = 0.029
12830 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.01Δρmax = 0.57 e Å−3
3412 reflectionsΔρmin = −0.39 e Å−3
187 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
Pd0.25000.75001.00000.03581 (10)
O0.25231 (10)0.8334 (5)0.92226 (8)0.0515 (6)
N10.34684 (10)0.4378 (5)0.95474 (9)0.0395 (5)
N20.32263 (10)0.5212 (5)0.99676 (9)0.0383 (5)
C10.28284 (12)0.7041 (7)0.88889 (11)0.0412 (7)
C20.32620 (11)0.5049 (7)0.90302 (10)0.0383 (6)
C30.35764 (12)0.3717 (7)0.86127 (11)0.0418 (7)
C40.40016 (14)0.1696 (8)0.87324 (13)0.0528 (8)
H4A0.40870.11520.90900.063*
C50.42950 (15)0.0503 (9)0.83250 (15)0.0667 (11)
H5A0.4575−0.08450.84100.080*
C60.41752 (17)0.1303 (11)0.77874 (15)0.0745 (12)
H6A0.43810.05190.75160.089*
C70.37581 (16)0.3227 (9)0.76598 (13)0.0625 (10)
H7A0.36750.37210.72990.075*
C80.34474 (13)0.4492 (8)0.80650 (12)0.0485 (8)
C90.30133 (14)0.6511 (8)0.79407 (12)0.0539 (8)
H9A0.29300.70180.75810.065*
C100.27170 (14)0.7722 (7)0.83272 (12)0.0492 (8)
H10A0.24330.90310.82270.059*
C110.35700 (12)0.4466 (6)1.04613 (11)0.0388 (6)
C120.33396 (14)0.2599 (7)1.08096 (12)0.0457 (7)
H12A0.29720.18451.07270.055*
C130.36591 (17)0.1857 (8)1.12820 (14)0.0611 (10)
H13A0.35100.05771.15160.073*
C140.41908 (16)0.3001 (9)1.14040 (14)0.0651 (11)
H14A0.44030.25191.17250.078*
C150.44195 (14)0.4868 (9)1.10574 (13)0.0596 (9)
H15A0.47860.56201.11480.071*
C160.41154 (12)0.5661 (7)1.05728 (12)0.0440 (7)
C170.43715 (16)0.7699 (8)1.02047 (16)0.0627 (10)
H17A0.41050.80020.98930.094*
H17B0.47330.69921.00900.094*
H17C0.44410.94131.03940.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd0.03590 (16)0.04187 (19)0.02960 (14)0.00156 (14)0.00184 (10)0.00060 (13)
O0.0571 (13)0.0640 (16)0.0342 (10)0.0177 (11)0.0081 (9)0.0076 (10)
N10.0398 (12)0.0433 (15)0.0354 (11)0.0000 (11)0.0026 (9)−0.0019 (11)
N20.0404 (11)0.0421 (15)0.0323 (11)0.0021 (11)0.0021 (9)0.0013 (10)
C10.0402 (14)0.052 (2)0.0315 (13)−0.0049 (13)0.0044 (10)0.0024 (12)
C20.0361 (13)0.0445 (18)0.0347 (13)−0.0046 (13)0.0039 (10)−0.0028 (12)
C30.0395 (14)0.0472 (18)0.0391 (14)−0.0061 (14)0.0050 (11)−0.0055 (14)
C40.0454 (16)0.066 (2)0.0477 (17)0.0004 (16)0.0053 (13)−0.0095 (16)
C50.0541 (19)0.079 (3)0.068 (2)0.010 (2)0.0079 (16)−0.021 (2)
C60.064 (2)0.104 (3)0.057 (2)0.000 (2)0.0198 (18)−0.029 (2)
C70.065 (2)0.085 (3)0.0382 (16)−0.011 (2)0.0101 (15)−0.0117 (17)
C80.0511 (16)0.057 (2)0.0376 (14)−0.0127 (16)0.0069 (12)−0.0082 (14)
C90.0611 (19)0.069 (2)0.0310 (14)−0.0072 (18)0.0005 (13)0.0014 (15)
C100.0522 (17)0.060 (2)0.0348 (14)0.0043 (16)0.0003 (12)0.0058 (15)
C110.0445 (14)0.0389 (17)0.0331 (13)0.0084 (13)0.0033 (11)0.0005 (12)
C120.0480 (16)0.0443 (18)0.0450 (15)0.0010 (15)0.0046 (12)0.0043 (15)
C130.071 (2)0.065 (3)0.0487 (18)0.0165 (19)0.0145 (16)0.0212 (17)
C140.062 (2)0.092 (3)0.0404 (16)0.020 (2)−0.0032 (15)0.0148 (18)
C150.0460 (17)0.078 (3)0.0535 (19)0.0068 (18)−0.0068 (14)−0.0013 (19)
C160.0412 (14)0.048 (2)0.0431 (15)0.0036 (14)0.0017 (12)0.0015 (14)
C170.0535 (19)0.068 (3)0.067 (2)−0.0060 (18)0.0039 (16)0.0064 (19)
Geometric parameters (Å, º) top
Pd—O1.9687 (19)C7—H7A0.9300
Pd—Oi1.9688 (19)C8—C91.414 (5)
Pd—N22.010 (2)C9—C101.347 (5)
Pd—N2i2.010 (2)C9—H9A0.9300
O—C11.284 (4)C10—H10A0.9300
N1—N21.279 (3)C11—C121.380 (4)
N1—C21.371 (3)C11—C161.390 (4)
N2—C111.451 (3)C12—C131.382 (4)
C1—C21.412 (4)C12—H12A0.9300
C1—C101.433 (4)C13—C141.356 (5)
C2—C31.453 (4)C13—H13A0.9300
C3—C41.399 (5)C14—C151.375 (5)
C3—C81.416 (4)C14—H14A0.9300
C4—C51.379 (5)C15—C161.397 (4)
C4—H4A0.9300C15—H15A0.9300
C5—C61.393 (5)C16—C171.492 (5)
C5—H5A0.9300C17—H17A0.9600
C6—C71.357 (6)C17—H17B0.9600
C6—H6A0.9300C17—H17C0.9600
C7—C81.412 (4)
O—Pd—Oi180.00 (13)C7—C8—C3118.9 (3)
O—Pd—N289.58 (9)C9—C8—C3119.1 (3)
Oi—Pd—N290.43 (9)C10—C9—C8122.1 (3)
O—Pd—N2i90.43 (9)C10—C9—H9A119.0
Oi—Pd—N2i89.57 (9)C8—C9—H9A119.0
N2—Pd—N2i180.00 (14)C9—C10—C1121.6 (3)
C1—O—Pd125.6 (2)C9—C10—H10A119.2
N2—N1—C2122.8 (2)C1—C10—H10A119.2
N1—N2—C11111.3 (2)C12—C11—C16122.0 (3)
N1—N2—Pd128.15 (18)C12—C11—N2118.5 (3)
C11—N2—Pd120.46 (17)C16—C11—N2119.5 (3)
O—C1—C2125.6 (3)C11—C12—C13119.5 (3)
O—C1—C10116.3 (3)C11—C12—H12A120.2
C2—C1—C10118.0 (3)C13—C12—H12A120.2
N1—C2—C1125.7 (3)C14—C13—C12119.9 (3)
N1—C2—C3113.7 (3)C14—C13—H13A120.1
C1—C2—C3120.4 (3)C12—C13—H13A120.1
C4—C3—C8118.8 (3)C13—C14—C15120.6 (3)
C4—C3—C2122.4 (3)C13—C14—H14A119.7
C8—C3—C2118.8 (3)C15—C14—H14A119.7
C5—C4—C3120.6 (3)C14—C15—C16121.6 (3)
C5—C4—H4A119.7C14—C15—H15A119.2
C3—C4—H4A119.7C16—C15—H15A119.2
C4—C5—C6120.5 (4)C11—C16—C15116.4 (3)
C4—C5—H5A119.7C11—C16—C17123.0 (3)
C6—C5—H5A119.7C15—C16—C17120.6 (3)
C7—C6—C5120.0 (3)C16—C17—H17A109.5
C7—C6—H6A120.0C16—C17—H17B109.5
C5—C6—H6A120.0H17A—C17—H17B109.5
C6—C7—C8121.2 (3)C16—C17—H17C109.5
C6—C7—H7A119.4H17A—C17—H17C109.5
C8—C7—H7A119.4H17B—C17—H17C109.5
C7—C8—C9122.0 (3)
N2—Pd—O—C115.3 (3)C6—C7—C8—C3−0.1 (6)
N2i—Pd—O—C1−164.7 (3)C4—C3—C8—C7−0.9 (5)
C2—N1—N2—C11−173.5 (3)C2—C3—C8—C7179.2 (3)
C2—N1—N2—Pd2.2 (4)C4—C3—C8—C9179.3 (3)
O—Pd—N2—N1−12.3 (3)C2—C3—C8—C9−0.7 (5)
Oi—Pd—N2—N1167.7 (3)C7—C8—C9—C10−179.9 (3)
O—Pd—N2—C11163.1 (2)C3—C8—C9—C10−0.1 (5)
Oi—Pd—N2—C11−16.9 (2)C8—C9—C10—C10.4 (5)
Pd—O—C1—C2−9.3 (5)O—C1—C10—C9179.6 (3)
Pd—O—C1—C10171.2 (2)C2—C1—C10—C90.1 (5)
N2—N1—C2—C110.7 (5)N1—N2—C11—C12−114.3 (3)
N2—N1—C2—C3−175.7 (3)Pd—N2—C11—C1269.6 (3)
O—C1—C2—N1−7.1 (5)N1—N2—C11—C1666.3 (4)
C10—C1—C2—N1172.4 (3)Pd—N2—C11—C16−109.8 (3)
O—C1—C2—C3179.7 (3)C16—C11—C12—C13−0.7 (5)
C10—C1—C2—C3−0.9 (4)N2—C11—C12—C13180.0 (3)
N1—C2—C3—C47.2 (4)C11—C12—C13—C141.1 (5)
C1—C2—C3—C4−178.8 (3)C12—C13—C14—C15−0.9 (6)
N1—C2—C3—C8−172.9 (3)C13—C14—C15—C160.3 (6)
C1—C2—C3—C81.2 (4)C12—C11—C16—C150.1 (5)
C8—C3—C4—C50.8 (5)N2—C11—C16—C15179.4 (3)
C2—C3—C4—C5−179.3 (3)C12—C11—C16—C17−179.5 (3)
C3—C4—C5—C60.4 (6)N2—C11—C16—C17−0.2 (5)
C4—C5—C6—C7−1.4 (7)C14—C15—C16—C110.1 (5)
C5—C6—C7—C81.3 (7)C14—C15—C16—C17179.7 (4)
C6—C7—C8—C9179.7 (4)
Symmetry code: (i) −x+1/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula[Pd(C17H13N2O)2]
Mr628.99
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)22.9997 (7), 4.8374 (2), 24.7294 (7)
β (°) 94.151 (2)
V (Å3)2744.15 (16)
Z4
Radiation typeMo Kα
µ (mm−1)0.72
Crystal size (mm)0.53 × 0.28 × 0.15
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.783, 0.900
No. of measured, independent and
observed [I > 2σ(I)] reflections		12830, 3412, 2463
Rint0.029
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.091, 1.01
No. of reflections3412
No. of parameters187
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.57, −0.39

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

 

Acknowledgements

We gratefully acknowledge financial support in part from the National Science Council, Taiwan (NSC97–2113-M-033–005-MY2) and in part from the CYCU Distinctive Research Area project in Chung Yuan Christian University, Taiwan (CYCU–98–CR–CH).

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBrayton, D. F., Larkin, T. M., Vicic, D. A. & Navarro, O. (2009). J. Organomet. Chem. 576, 3008–3011.  Web of Science CrossRef Google Scholar
 First citationBruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationLai, Y.-C., Chen, H.-Y., Hung, W.-C., Lin, C.-C. & Hong, F.-E. (2005). Tetrahedron, 61, 9484–9489.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTsai, C.-Y., Lin, C.-H. & Ko, B.-T. (2009). Acta Cryst. E65, m619.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page m1022
https://doi.org/10.1107/S1600536810028916
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