Bis{2-[1-(benzyl-imino)-eth-yl]phenolato}palladium(II).

In the title compound, [Pd(C(15)H(14)NO)(2)], the Pd atom lies on an inversion center and is coordinated by two ligand mol-ecules through the O and N atoms in a bidentate manner, forming a slightly distorted square-planar geometry. The dihedral angle between the two benzene rings in the ligand is 76.53 (19)°. The mol-ecular packing is stablized by C-H⋯O and C-H⋯π inter-actions.

Related literature

For the catalytic activity of palladium(II)–Schiff base complexes, see: Gupta & Sutar (2008 ▶); Lai et al. (2005 ▶) and for their anti­tumor activity, see: Garoufis et al. (2008 ▶). For related structures, see: Adrian et al. (2008 ▶); Wan Nazihah Wan Ibrahim et al. (2008 ▶); Chen & Xia (2009 ▶). For bond-length data, see: Allen et al. (2002 ▶).

Experimental

Crystal data

[Pd(C15H14NO)2]

M = 554.94

Monoclinic,

a = 11.188 (2) Å

b = 9.4460 (17) Å

c = 11.984 (2) Å

β = 110.558 (4)°

V = 1185.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.81 mm−1

T = 298 K

0.28 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.804, T max = 0.908

6420 measured reflections

2177 independent reflections

1939 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.109

S = 1.18

2177 reflections

161 parameters

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −0.98 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT (Bruker, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031375/pv2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031375/pv2311Isup2.hkl

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

[Pd(C15H14NO)2]	F(000) = 568
Mr = 554.94	Dx = 1.554 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4170 reflections
a = 11.188 (2) Å	θ = 2.1–25.5°
b = 9.4460 (17) Å	µ = 0.81 mm−1
c = 11.984 (2) Å	T = 298 K
β = 110.558 (4)°	Block, yellow
V = 1185.8 (4) Å3	0.28 × 0.20 × 0.12 mm
Z = 2

Bruker SMART APEX CCD area-detector diffractometer	2177 independent reflections
Radiation source: fine-focus sealed tube	1939 reflections with I > 2/s(I)
graphite	Rint = 0.038
Detector resolution: 83.66 pixels mm-1	θmax = 25.5°, θmin = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −11→11
Tmin = 0.804, Tmax = 0.908	l = −14→11
6420 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.7043P] where P = (Fo2 + 2Fc2)/3
2177 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.88 e Å−3
0 restraints	Δρmin = −0.98 e Å−3

Experimental. Analytical calculation for C30H28N2O2Pd: C,64.93; H,5.09; N,5.05. Found: C,64.58; H,4.97; N,4.94. IR (cm-1): v(C=N) 1586, v(C—O) 1323, v(C—H) 2977, v(C—N) 1355, v(Pd—O) 695, v(Pd—N) 476.

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
Pd1	0.5000	0.5000	0.0000	0.02879 (16)
O1	0.4462 (2)	0.5912 (3)	0.1236 (2)	0.0409 (6)
N1	0.6541 (2)	0.6317 (3)	0.0459 (2)	0.0323 (6)
C1	0.5319 (3)	0.6226 (3)	0.2285 (3)	0.0335 (7)
C2	0.4944 (3)	0.6076 (4)	0.3284 (3)	0.0422 (8)
H2A	0.4128	0.5748	0.3178	0.051*
C3	0.5765 (4)	0.6406 (4)	0.4419 (3)	0.0468 (9)
H3A	0.5503	0.6291	0.5069	0.056*
C4	0.6971 (4)	0.6906 (4)	0.4583 (4)	0.0498 (10)
H4A	0.7529	0.7116	0.5346	0.060*
C5	0.7346 (3)	0.7095 (4)	0.3632 (4)	0.0428 (9)
H5A	0.8156	0.7458	0.3760	0.051*
C6	0.6551 (3)	0.6758 (3)	0.2454 (3)	0.0326 (7)
C7	0.7007 (3)	0.6991 (3)	0.1464 (3)	0.0335 (7)
C8	0.8047 (4)	0.8088 (4)	0.1658 (4)	0.0437 (9)
H8A	0.7961	0.8529	0.0912	0.066*
H8B	0.8867	0.7638	0.1977	0.066*
H8C	0.7974	0.8793	0.2208	0.066*
C9	0.7070 (3)	0.6577 (3)	−0.0483 (3)	0.0347 (7)
H9A	0.6993	0.5717	−0.0945	0.042*
H9B	0.7972	0.6790	−0.0114	0.042*
C10	0.6432 (3)	0.7774 (3)	−0.1320 (3)	0.0321 (7)
C11	0.5685 (3)	0.8786 (4)	−0.1050 (3)	0.0423 (8)
H11A	0.5541	0.8737	−0.0333	0.051*
C12	0.5149 (5)	0.9877 (4)	−0.1846 (5)	0.0554 (12)
H12A	0.4646	1.0553	−0.1657	0.066*
C13	0.5354 (6)	0.9965 (4)	−0.2906 (5)	0.0569 (13)
H13A	0.4998	1.0701	−0.3432	0.068*
C14	0.6090 (4)	0.8957 (4)	−0.3186 (4)	0.0531 (10)
H14A	0.6231	0.9007	−0.3905	0.064*
C15	0.6619 (3)	0.7873 (4)	−0.2398 (3)	0.0438 (9)
H15A	0.7112	0.7193	−0.2595	0.053*

	U11	U22	U33	U12	U13	U23
Pd1	0.0270 (2)	0.0261 (2)	0.0302 (3)	−0.00145 (11)	0.00621 (17)	0.00023 (12)
O1	0.0325 (12)	0.0481 (14)	0.0402 (14)	−0.0030 (10)	0.0104 (11)	−0.0108 (11)
N1	0.0297 (13)	0.0273 (13)	0.0396 (16)	0.0003 (11)	0.0116 (12)	0.0024 (12)
C1	0.0351 (16)	0.0236 (15)	0.039 (2)	0.0035 (13)	0.0098 (15)	−0.0020 (14)
C2	0.0437 (19)	0.0346 (18)	0.053 (2)	−0.0016 (15)	0.0227 (18)	−0.0025 (16)
C3	0.057 (2)	0.049 (2)	0.036 (2)	0.0019 (18)	0.0177 (18)	−0.0037 (17)
C4	0.053 (2)	0.054 (2)	0.034 (2)	0.0033 (18)	0.0051 (18)	−0.0084 (18)
C5	0.0366 (18)	0.041 (2)	0.046 (2)	0.0004 (15)	0.0083 (17)	−0.0055 (17)
C6	0.0357 (16)	0.0268 (16)	0.0317 (18)	0.0023 (13)	0.0074 (14)	−0.0005 (13)
C7	0.0301 (16)	0.0257 (15)	0.038 (2)	0.0009 (13)	0.0041 (14)	0.0009 (14)
C8	0.0424 (19)	0.0353 (19)	0.050 (2)	−0.0090 (15)	0.0115 (18)	−0.0001 (17)
C9	0.0300 (16)	0.0345 (17)	0.040 (2)	−0.0021 (13)	0.0133 (15)	−0.0002 (14)
C10	0.0320 (16)	0.0330 (16)	0.0305 (18)	−0.0065 (13)	0.0099 (14)	−0.0012 (14)
C11	0.053 (2)	0.043 (2)	0.0287 (19)	0.0076 (16)	0.0111 (16)	0.0007 (16)
C12	0.074 (3)	0.040 (2)	0.052 (3)	0.0167 (18)	0.021 (3)	0.0026 (17)
C13	0.076 (4)	0.038 (2)	0.051 (3)	0.0001 (17)	0.016 (3)	0.0121 (16)
C14	0.072 (3)	0.051 (2)	0.043 (2)	−0.010 (2)	0.029 (2)	0.0042 (18)
C15	0.050 (2)	0.043 (2)	0.046 (2)	−0.0010 (16)	0.0268 (18)	−0.0005 (17)

Pd1—O1	1.981 (2)	C7—C8	1.514 (4)
Pd1—O1i	1.981 (2)	C8—H8A	0.9600
Pd1—N1i	2.039 (3)	C8—H8B	0.9600
Pd1—N1	2.039 (3)	C8—H8C	0.9600
O1—C1	1.319 (4)	C9—C10	1.514 (5)
N1—C7	1.299 (4)	C9—H9A	0.9700
N1—C9	1.468 (4)	C9—H9B	0.9700
C1—C2	1.407 (5)	C10—C11	1.380 (5)
C1—C6	1.414 (4)	C10—C15	1.382 (5)
C2—C3	1.384 (5)	C11—C12	1.389 (6)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.377 (5)	C12—C13	1.371 (8)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.357 (6)	C13—C14	1.375 (6)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.415 (5)	C14—C15	1.377 (6)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.463 (5)	C15—H15A	0.9300
O1—Pd1—O1i	180.00 (8)	C7—C8—H8A	109.5
O1—Pd1—N1i	90.97 (10)	C7—C8—H8B	109.5
O1i—Pd1—N1i	89.03 (10)	H8A—C8—H8B	109.5
O1—Pd1—N1	89.03 (10)	C7—C8—H8C	109.5
O1i—Pd1—N1	90.97 (10)	H8A—C8—H8C	109.5
N1i—Pd1—N1	180.00 (11)	H8B—C8—H8C	109.5
C1—O1—Pd1	120.0 (2)	N1—C9—C10	114.3 (3)
C7—N1—C9	119.5 (3)	N1—C9—H9A	108.7
C7—N1—Pd1	125.1 (2)	C10—C9—H9A	108.7
C9—N1—Pd1	115.2 (2)	N1—C9—H9B	108.7
O1—C1—C2	117.0 (3)	C10—C9—H9B	108.7
O1—C1—C6	124.2 (3)	H9A—C9—H9B	107.6
C2—C1—C6	118.7 (3)	C11—C10—C15	118.3 (3)
C3—C2—C1	121.4 (3)	C11—C10—C9	123.0 (3)
C3—C2—H2A	119.3	C15—C10—C9	118.6 (3)
C1—C2—H2A	119.3	C10—C11—C12	120.3 (4)
C4—C3—C2	119.7 (3)	C10—C11—H11A	119.9
C4—C3—H3A	120.1	C12—C11—H11A	119.9
C2—C3—H3A	120.1	C13—C12—C11	120.5 (4)
C5—C4—C3	120.1 (4)	C13—C12—H12A	119.7
C5—C4—H4A	119.9	C11—C12—H12A	119.7
C3—C4—H4A	119.9	C12—C13—C14	119.6 (4)
C4—C5—C6	122.4 (4)	C12—C13—H13A	120.2
C4—C5—H5A	118.8	C14—C13—H13A	120.2
C6—C5—H5A	118.8	C13—C14—C15	119.8 (4)
C1—C6—C5	117.6 (3)	C13—C14—H14A	120.1
C1—C6—C7	122.5 (3)	C15—C14—H14A	120.1
C5—C6—C7	119.9 (3)	C14—C15—C10	121.4 (3)
N1—C7—C6	122.5 (3)	C14—C15—H15A	119.3
N1—C7—C8	120.9 (3)	C10—C15—H15A	119.3
C6—C7—C8	116.5 (3)
O1i—Pd1—O1—C1	−151 (100)	C4—C5—C6—C7	179.6 (3)
N1i—Pd1—O1—C1	138.5 (2)	C9—N1—C7—C6	−178.3 (3)
N1—Pd1—O1—C1	−41.5 (2)	Pd1—N1—C7—C6	6.9 (4)
O1—Pd1—N1—C7	20.0 (3)	C9—N1—C7—C8	2.7 (4)
O1i—Pd1—N1—C7	−160.0 (3)	Pd1—N1—C7—C8	−172.1 (2)
N1i—Pd1—N1—C7	156 (100)	C1—C6—C7—N1	−24.1 (5)
O1—Pd1—N1—C9	−155.0 (2)	C5—C6—C7—N1	157.2 (3)
O1i—Pd1—N1—C9	25.0 (2)	C1—C6—C7—C8	155.0 (3)
N1i—Pd1—N1—C9	−19 (100)	C5—C6—C7—C8	−23.7 (5)
Pd1—O1—C1—C2	−144.1 (2)	C7—N1—C9—C10	−89.1 (3)
Pd1—O1—C1—C6	38.9 (4)	Pd1—N1—C9—C10	86.1 (3)
O1—C1—C2—C3	−178.7 (3)	N1—C9—C10—C11	17.5 (4)
C6—C1—C2—C3	−1.5 (5)	N1—C9—C10—C15	−163.5 (3)
C1—C2—C3—C4	0.7 (6)	C15—C10—C11—C12	−0.5 (6)
C2—C3—C4—C5	1.0 (6)	C9—C10—C11—C12	178.6 (4)
C3—C4—C5—C6	−1.8 (6)	C10—C11—C12—C13	−0.1 (7)
O1—C1—C6—C5	177.7 (3)	C11—C12—C13—C14	0.5 (8)
C2—C1—C6—C5	0.7 (4)	C12—C13—C14—C15	−0.3 (7)
O1—C1—C6—C7	−1.0 (5)	C13—C14—C15—C10	−0.3 (6)
C2—C1—C6—C7	−178.0 (3)	C11—C10—C15—C14	0.7 (5)
C4—C5—C6—C1	0.9 (5)	C9—C10—C15—C14	−178.4 (3)

Cg3 and Cg4 are the centroids of the ???? and ???? rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.97	2.18	2.862 (4)	127
C11—H11A···N1	0.93	2.58	2.900 (5)	101
C8—H8B···Cg4ii	0.96	2.57	3.523 (5)	172
C13—H13A···Cg3iii	0.93	2.87	3.626 (5)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C1–C6 and C10–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.97	2.18	2.862 (4)	127
C8—H8B⋯Cg4ii	0.96	2.57	3.523 (5)	172
C13—H13A⋯Cg3iii	0.93	2.87	3.626 (5)	139

Symmetry codes: (i) ; (ii) ; (iii) .