Bis{1-[(E)-(2-methyl-phen-yl)diazen-yl]-2-naphtho-lato}palladium(II).

In the title compound, [Pd(C(17)H(13)N(2)O)(2)], the Pd(II) atom is tetra-coordinated by two N atoms and two O atoms from two bidentate methylphenyl-diazenylnaphtolate ligands, forming a square-planar complex. The two N atoms and two O atoms around the Pd(II) atom are trans to each other (as the Pd(II) 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 Pd(II) 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 ▶). 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

Crystal data

[Pd(C17H13N2O)2]

M = 628.99

Monoclinic,

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 ▶) T min = 0.783, T max = 0.900

12830 measured reflections

3412 independent reflections

2463 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 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 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028916/nk2047Isup2.hkl

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

[Pd(C17H13N2O)2]	F(000) = 1280
Mr = 628.99	Dx = 1.522 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7356 reflections
a = 22.9997 (7) Å	θ = 2.3–28.2°
b = 4.8374 (2) Å	µ = 0.72 mm−1
c = 24.7294 (7) Å	T = 296 K
β = 94.151 (2)°	Block, purple
V = 2744.15 (16) Å3	0.53 × 0.28 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	3412 independent reflections
Radiation source: fine-focus sealed tube	2463 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 1.7°
φ and ω scans	h = −29→30
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −6→6
Tmin = 0.783, Tmax = 0.900	l = −32→32
12830 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0308P)2 + 8.4214P] where P = (Fo2 + 2Fc2)/3
3412 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
Pd	0.2500	0.7500	1.0000	0.03581 (10)
O	0.25231 (10)	0.8334 (5)	0.92226 (8)	0.0515 (6)
N1	0.34684 (10)	0.4378 (5)	0.95474 (9)	0.0395 (5)
N2	0.32263 (10)	0.5212 (5)	0.99676 (9)	0.0383 (5)
C1	0.28284 (12)	0.7041 (7)	0.88889 (11)	0.0412 (7)
C2	0.32620 (11)	0.5049 (7)	0.90302 (10)	0.0383 (6)
C3	0.35764 (12)	0.3717 (7)	0.86127 (11)	0.0418 (7)
C4	0.40016 (14)	0.1696 (8)	0.87324 (13)	0.0528 (8)
H4A	0.4087	0.1152	0.9090	0.063*
C5	0.42950 (15)	0.0503 (9)	0.83250 (15)	0.0667 (11)
H5A	0.4575	−0.0845	0.8410	0.080*
C6	0.41752 (17)	0.1303 (11)	0.77874 (15)	0.0745 (12)
H6A	0.4381	0.0519	0.7516	0.089*
C7	0.37581 (16)	0.3227 (9)	0.76598 (13)	0.0625 (10)
H7A	0.3675	0.3721	0.7299	0.075*
C8	0.34474 (13)	0.4492 (8)	0.80650 (12)	0.0485 (8)
C9	0.30133 (14)	0.6511 (8)	0.79407 (12)	0.0539 (8)
H9A	0.2930	0.7018	0.7581	0.065*
C10	0.27170 (14)	0.7722 (7)	0.83272 (12)	0.0492 (8)
H10A	0.2433	0.9031	0.8227	0.059*
C11	0.35700 (12)	0.4466 (6)	1.04613 (11)	0.0388 (6)
C12	0.33396 (14)	0.2599 (7)	1.08096 (12)	0.0457 (7)
H12A	0.2972	0.1845	1.0727	0.055*
C13	0.36591 (17)	0.1857 (8)	1.12820 (14)	0.0611 (10)
H13A	0.3510	0.0577	1.1516	0.073*
C14	0.41908 (16)	0.3001 (9)	1.14040 (14)	0.0651 (11)
H14A	0.4403	0.2519	1.1725	0.078*
C15	0.44195 (14)	0.4868 (9)	1.10574 (13)	0.0596 (9)
H15A	0.4786	0.5620	1.1148	0.071*
C16	0.41154 (12)	0.5661 (7)	1.05728 (12)	0.0440 (7)
C17	0.43715 (16)	0.7699 (8)	1.02047 (16)	0.0627 (10)
H17A	0.4105	0.8002	0.9893	0.094*
H17B	0.4733	0.6992	1.0090	0.094*
H17C	0.4441	0.9413	1.0394	0.094*

	U11	U22	U33	U12	U13	U23
Pd	0.03590 (16)	0.04187 (19)	0.02960 (14)	0.00156 (14)	0.00184 (10)	0.00060 (13)
O	0.0571 (13)	0.0640 (16)	0.0342 (10)	0.0177 (11)	0.0081 (9)	0.0076 (10)
N1	0.0398 (12)	0.0433 (15)	0.0354 (11)	0.0000 (11)	0.0026 (9)	−0.0019 (11)
N2	0.0404 (11)	0.0421 (15)	0.0323 (11)	0.0021 (11)	0.0021 (9)	0.0013 (10)
C1	0.0402 (14)	0.052 (2)	0.0315 (13)	−0.0049 (13)	0.0044 (10)	0.0024 (12)
C2	0.0361 (13)	0.0445 (18)	0.0347 (13)	−0.0046 (13)	0.0039 (10)	−0.0028 (12)
C3	0.0395 (14)	0.0472 (18)	0.0391 (14)	−0.0061 (14)	0.0050 (11)	−0.0055 (14)
C4	0.0454 (16)	0.066 (2)	0.0477 (17)	0.0004 (16)	0.0053 (13)	−0.0095 (16)
C5	0.0541 (19)	0.079 (3)	0.068 (2)	0.010 (2)	0.0079 (16)	−0.021 (2)
C6	0.064 (2)	0.104 (3)	0.057 (2)	0.000 (2)	0.0198 (18)	−0.029 (2)
C7	0.065 (2)	0.085 (3)	0.0382 (16)	−0.011 (2)	0.0101 (15)	−0.0117 (17)
C8	0.0511 (16)	0.057 (2)	0.0376 (14)	−0.0127 (16)	0.0069 (12)	−0.0082 (14)
C9	0.0611 (19)	0.069 (2)	0.0310 (14)	−0.0072 (18)	0.0005 (13)	0.0014 (15)
C10	0.0522 (17)	0.060 (2)	0.0348 (14)	0.0043 (16)	0.0003 (12)	0.0058 (15)
C11	0.0445 (14)	0.0389 (17)	0.0331 (13)	0.0084 (13)	0.0033 (11)	0.0005 (12)
C12	0.0480 (16)	0.0443 (18)	0.0450 (15)	0.0010 (15)	0.0046 (12)	0.0043 (15)
C13	0.071 (2)	0.065 (3)	0.0487 (18)	0.0165 (19)	0.0145 (16)	0.0212 (17)
C14	0.062 (2)	0.092 (3)	0.0404 (16)	0.020 (2)	−0.0032 (15)	0.0148 (18)
C15	0.0460 (17)	0.078 (3)	0.0535 (19)	0.0068 (18)	−0.0068 (14)	−0.0013 (19)
C16	0.0412 (14)	0.048 (2)	0.0431 (15)	0.0036 (14)	0.0017 (12)	0.0015 (14)
C17	0.0535 (19)	0.068 (3)	0.067 (2)	−0.0060 (18)	0.0039 (16)	0.0064 (19)

Pd—O	1.9687 (19)	C7—H7A	0.9300
Pd—Oi	1.9688 (19)	C8—C9	1.414 (5)
Pd—N2	2.010 (2)	C9—C10	1.347 (5)
Pd—N2i	2.010 (2)	C9—H9A	0.9300
O—C1	1.284 (4)	C10—H10A	0.9300
N1—N2	1.279 (3)	C11—C12	1.380 (4)
N1—C2	1.371 (3)	C11—C16	1.390 (4)
N2—C11	1.451 (3)	C12—C13	1.382 (4)
C1—C2	1.412 (4)	C12—H12A	0.9300
C1—C10	1.433 (4)	C13—C14	1.356 (5)
C2—C3	1.453 (4)	C13—H13A	0.9300
C3—C4	1.399 (5)	C14—C15	1.375 (5)
C3—C8	1.416 (4)	C14—H14A	0.9300
C4—C5	1.379 (5)	C15—C16	1.397 (4)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.393 (5)	C16—C17	1.492 (5)
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.357 (6)	C17—H17B	0.9600
C6—H6A	0.9300	C17—H17C	0.9600
C7—C8	1.412 (4)
O—Pd—Oi	180.00 (13)	C7—C8—C3	118.9 (3)
O—Pd—N2	89.58 (9)	C9—C8—C3	119.1 (3)
Oi—Pd—N2	90.43 (9)	C10—C9—C8	122.1 (3)
O—Pd—N2i	90.43 (9)	C10—C9—H9A	119.0
Oi—Pd—N2i	89.57 (9)	C8—C9—H9A	119.0
N2—Pd—N2i	180.00 (14)	C9—C10—C1	121.6 (3)
C1—O—Pd	125.6 (2)	C9—C10—H10A	119.2
N2—N1—C2	122.8 (2)	C1—C10—H10A	119.2
N1—N2—C11	111.3 (2)	C12—C11—C16	122.0 (3)
N1—N2—Pd	128.15 (18)	C12—C11—N2	118.5 (3)
C11—N2—Pd	120.46 (17)	C16—C11—N2	119.5 (3)
O—C1—C2	125.6 (3)	C11—C12—C13	119.5 (3)
O—C1—C10	116.3 (3)	C11—C12—H12A	120.2
C2—C1—C10	118.0 (3)	C13—C12—H12A	120.2
N1—C2—C1	125.7 (3)	C14—C13—C12	119.9 (3)
N1—C2—C3	113.7 (3)	C14—C13—H13A	120.1
C1—C2—C3	120.4 (3)	C12—C13—H13A	120.1
C4—C3—C8	118.8 (3)	C13—C14—C15	120.6 (3)
C4—C3—C2	122.4 (3)	C13—C14—H14A	119.7
C8—C3—C2	118.8 (3)	C15—C14—H14A	119.7
C5—C4—C3	120.6 (3)	C14—C15—C16	121.6 (3)
C5—C4—H4A	119.7	C14—C15—H15A	119.2
C3—C4—H4A	119.7	C16—C15—H15A	119.2
C4—C5—C6	120.5 (4)	C11—C16—C15	116.4 (3)
C4—C5—H5A	119.7	C11—C16—C17	123.0 (3)
C6—C5—H5A	119.7	C15—C16—C17	120.6 (3)
C7—C6—C5	120.0 (3)	C16—C17—H17A	109.5
C7—C6—H6A	120.0	C16—C17—H17B	109.5
C5—C6—H6A	120.0	H17A—C17—H17B	109.5
C6—C7—C8	121.2 (3)	C16—C17—H17C	109.5
C6—C7—H7A	119.4	H17A—C17—H17C	109.5
C8—C7—H7A	119.4	H17B—C17—H17C	109.5
C7—C8—C9	122.0 (3)
N2—Pd—O—C1	15.3 (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—C7	179.2 (3)
C2—N1—N2—Pd	2.2 (4)	C4—C3—C8—C9	179.3 (3)
O—Pd—N2—N1	−12.3 (3)	C2—C3—C8—C9	−0.7 (5)
Oi—Pd—N2—N1	167.7 (3)	C7—C8—C9—C10	−179.9 (3)
O—Pd—N2—C11	163.1 (2)	C3—C8—C9—C10	−0.1 (5)
Oi—Pd—N2—C11	−16.9 (2)	C8—C9—C10—C1	0.4 (5)
Pd—O—C1—C2	−9.3 (5)	O—C1—C10—C9	179.6 (3)
Pd—O—C1—C10	171.2 (2)	C2—C1—C10—C9	0.1 (5)
N2—N1—C2—C1	10.7 (5)	N1—N2—C11—C12	−114.3 (3)
N2—N1—C2—C3	−175.7 (3)	Pd—N2—C11—C12	69.6 (3)
O—C1—C2—N1	−7.1 (5)	N1—N2—C11—C16	66.3 (4)
C10—C1—C2—N1	172.4 (3)	Pd—N2—C11—C16	−109.8 (3)
O—C1—C2—C3	179.7 (3)	C16—C11—C12—C13	−0.7 (5)
C10—C1—C2—C3	−0.9 (4)	N2—C11—C12—C13	180.0 (3)
N1—C2—C3—C4	7.2 (4)	C11—C12—C13—C14	1.1 (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—C16	0.3 (6)
C1—C2—C3—C8	1.2 (4)	C12—C11—C16—C15	0.1 (5)
C8—C3—C4—C5	0.8 (5)	N2—C11—C16—C15	179.4 (3)
C2—C3—C4—C5	−179.3 (3)	C12—C11—C16—C17	−179.5 (3)
C3—C4—C5—C6	0.4 (6)	N2—C11—C16—C17	−0.2 (5)
C4—C5—C6—C7	−1.4 (7)	C14—C15—C16—C11	0.1 (5)
C5—C6—C7—C8	1.3 (7)	C14—C15—C16—C17	179.7 (4)
C6—C7—C8—C9	179.7 (4)