{5,5'-Dimeth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenolato}palladium(II).

In the title compound, [Pd(C(21)H(24)N(2)O(4))], the complete mol-ecule is generated by crystallographic mirror symmetry with the Pd and three C atoms lying on the mirror plane. The Pd-O and Pd-N distances are 1.9932 (6) and 2.0029 (7) Å, respectively. The dihedral angle between two benzene rings of the ligand is 79.21 (4)°. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ab plane. These planes are further connected by C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For related structures, see: Wan Nazihah Wan Ibrahim et al. (2008 ▶); Montazerozohori et al. (2009 ▶). For background to applications of palladium(II) complexes, see: Gupta et al. (2009 ▶); Lu et al. (2010 ▶); He & Cai (2011 ▶); Garoufis et al. (2008 ▶); Kumar et al. (2009 ▶); Islam et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Pd(C21H24N2O4)]

M = 474.82

Orthorhombic,

a = 11.5470 (4) Å

b = 20.9656 (7) Å

c = 7.8730 (3) Å

V = 1905.97 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.00 mm−1

T = 100 K

0.27 × 0.24 × 0.18 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.773, T max = 0.839

30756 measured reflections

4296 independent reflections

4134 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.016

wR(F 2) = 0.043

S = 1.13

4296 reflections

134 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013128/kj2196sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013128/kj2196Isup2.hkl

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

[Pd(C21H24N2O4)]	F(000) = 968
Mr = 474.82	Dx = 1.655 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 9824 reflections
a = 11.5470 (4) Å	θ = 3.3–35.1°
b = 20.9656 (7) Å	µ = 1.00 mm−1
c = 7.8730 (3) Å	T = 100 K
V = 1905.97 (12) Å3	Block, yellow
Z = 4	0.27 × 0.24 × 0.18 mm

Bruker APEX DUO CCD area-detector diffractometer	4296 independent reflections
Radiation source: fine-focus sealed tube	4134 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 35.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.773, Tmax = 0.839	k = −33→33
30756 measured reflections	l = −8→12

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)] = 0.016	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.043	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0183P)2 + 0.777P] where P = (Fo2 + 2Fc2)/3
4296 reflections	(Δ/σ)max = 0.003
134 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.535617 (6)	0.2500	0.088830 (10)	0.00982 (2)
O1	0.42276 (5)	0.31425 (3)	0.17501 (8)	0.01411 (10)
O2	0.12833 (5)	0.45403 (3)	−0.02329 (9)	0.01723 (11)
N1	0.63494 (6)	0.31998 (3)	−0.00483 (9)	0.01240 (11)
C1	0.39331 (7)	0.36205 (4)	0.07712 (9)	0.01203 (11)
C2	0.27757 (7)	0.38427 (4)	0.08646 (10)	0.01310 (12)
H2A	0.2251	0.3651	0.1642	0.016*
C3	0.24037 (7)	0.43360 (4)	−0.01673 (10)	0.01370 (12)
C4	0.31792 (7)	0.46562 (4)	−0.12613 (11)	0.01645 (13)
H4A	0.2924	0.5004	−0.1939	0.020*
C5	0.43136 (7)	0.44543 (4)	−0.13264 (11)	0.01566 (13)
H5A	0.4844	0.4675	−0.2038	0.019*
C6	0.47127 (6)	0.39285 (4)	−0.03651 (10)	0.01282 (12)
C7	0.59049 (7)	0.37365 (4)	−0.05364 (10)	0.01349 (12)
H7A	0.6415	0.4033	−0.1059	0.016*
C8	0.76027 (6)	0.31049 (4)	−0.02515 (11)	0.01447 (13)
H8A	0.7964	0.3083	0.0887	0.017*
H8B	0.7932	0.3479	−0.0847	0.017*
C9	0.79183 (9)	0.2500	−0.12444 (14)	0.01195 (16)
C10	0.73574 (10)	0.2500	−0.29972 (15)	0.01630 (19)
H10A	0.7594	0.2874	−0.3609	0.024*
H10B	0.6530	0.2500	−0.2876	0.024*
C11	0.92430 (10)	0.2500	−0.14109 (16)	0.01623 (19)
H11A	0.9487	0.2874	−0.2017	0.024*
H11B	0.9584	0.2500	−0.0299	0.024*
C12	0.04407 (7)	0.41728 (5)	0.06862 (13)	0.01862 (15)
H12A	−0.0332	0.4353	0.0496	0.028*
H12B	0.0622	0.4185	0.1902	0.028*
H12C	0.0457	0.3730	0.0288	0.028*

	U11	U22	U33	U12	U13	U23
Pd1	0.00822 (4)	0.01192 (4)	0.00933 (4)	0.000	0.00093 (2)	0.000
O1	0.0140 (2)	0.0151 (2)	0.0133 (2)	0.00348 (18)	0.00348 (19)	0.00199 (19)
O2	0.0125 (2)	0.0189 (3)	0.0203 (3)	0.0032 (2)	0.0008 (2)	0.0040 (2)
N1	0.0097 (2)	0.0144 (3)	0.0131 (3)	−0.0006 (2)	0.0015 (2)	−0.0015 (2)
C1	0.0122 (3)	0.0127 (3)	0.0112 (3)	0.0005 (2)	0.0008 (2)	−0.0011 (2)
C2	0.0122 (3)	0.0141 (3)	0.0130 (3)	0.0013 (2)	0.0015 (2)	0.0002 (2)
C3	0.0129 (3)	0.0144 (3)	0.0137 (3)	0.0016 (2)	−0.0001 (2)	−0.0007 (2)
C4	0.0165 (3)	0.0157 (3)	0.0172 (3)	0.0016 (2)	0.0013 (3)	0.0036 (3)
C5	0.0163 (3)	0.0145 (3)	0.0162 (3)	0.0001 (2)	0.0027 (3)	0.0021 (2)
C6	0.0121 (3)	0.0128 (3)	0.0135 (3)	0.0000 (2)	0.0017 (2)	0.0001 (2)
C7	0.0126 (3)	0.0138 (3)	0.0140 (3)	−0.0013 (2)	0.0020 (2)	−0.0007 (2)
C8	0.0089 (3)	0.0173 (3)	0.0171 (3)	−0.0012 (2)	0.0013 (2)	−0.0035 (3)
C9	0.0088 (4)	0.0152 (4)	0.0119 (4)	0.000	0.0012 (3)	0.000
C10	0.0142 (4)	0.0232 (5)	0.0115 (4)	0.000	0.0000 (3)	0.000
C11	0.0097 (4)	0.0200 (5)	0.0189 (5)	0.000	0.0025 (4)	0.000
C12	0.0132 (3)	0.0195 (4)	0.0232 (4)	0.0009 (3)	0.0012 (3)	0.0018 (3)

Pd1—O1i	1.9932 (6)	C5—H5A	0.9500
Pd1—O1	1.9932 (6)	C6—C7	1.4406 (11)
Pd1—N1i	2.0029 (7)	C7—H7A	0.9500
Pd1—N1	2.0029 (7)	C8—C9	1.5337 (10)
O1—C1	1.3092 (9)	C8—H8A	0.9900
O2—C3	1.3637 (10)	C8—H8B	0.9900
O2—C12	1.4366 (11)	C9—C10	1.5244 (16)
N1—C7	1.2951 (10)	C9—C8i	1.5336 (10)
N1—C8	1.4695 (10)	C9—C11	1.5353 (15)
C1—C2	1.4172 (11)	C10—H10A	0.9600
C1—C6	1.4239 (11)	C10—H10B	0.9600
C2—C3	1.3835 (11)	C11—H11A	0.9599
C2—H2A	0.9500	C11—H11B	0.9600
C3—C4	1.4122 (12)	C12—H12A	0.9800
C4—C5	1.3776 (12)	C12—H12B	0.9800
C4—H4A	0.9500	C12—H12C	0.9800
C5—C6	1.4144 (11)
O1i—Pd1—O1	85.03 (3)	C1—C6—C7	122.43 (7)
O1i—Pd1—N1i	90.27 (3)	N1—C7—C6	126.41 (7)
O1—Pd1—N1i	174.10 (3)	N1—C7—H7A	116.8
O1i—Pd1—N1	174.10 (3)	C6—C7—H7A	116.8
O1—Pd1—N1	90.27 (3)	N1—C8—C9	113.67 (7)
N1i—Pd1—N1	94.20 (4)	N1—C8—H8A	108.8
C1—O1—Pd1	119.13 (5)	C9—C8—H8A	108.8
C3—O2—C12	117.06 (7)	N1—C8—H8B	108.8
C7—N1—C8	118.40 (7)	C9—C8—H8B	108.8
C7—N1—Pd1	121.25 (5)	H8A—C8—H8B	107.7
C8—N1—Pd1	120.32 (5)	C10—C9—C8i	111.13 (6)
O1—C1—C2	117.78 (7)	C10—C9—C8	111.13 (6)
O1—C1—C6	123.55 (7)	C8i—C9—C8	111.56 (9)
C2—C1—C6	118.67 (7)	C10—C9—C11	110.24 (9)
C3—C2—C1	120.53 (7)	C8i—C9—C11	106.28 (6)
C3—C2—H2A	119.7	C8—C9—C11	106.28 (6)
C1—C2—H2A	119.7	C9—C10—H10A	109.5
O2—C3—C2	123.47 (7)	C9—C10—H10B	109.5
O2—C3—C4	115.41 (7)	H10A—C10—H10B	109.5
C2—C3—C4	121.11 (7)	C9—C11—H11A	109.6
C5—C4—C3	118.66 (7)	C9—C11—H11B	109.3
C5—C4—H4A	120.7	H11A—C11—H11B	109.5
C3—C4—H4A	120.7	O2—C12—H12A	109.5
C4—C5—C6	121.96 (7)	O2—C12—H12B	109.5
C4—C5—H5A	119.0	H12A—C12—H12B	109.5
C6—C5—H5A	119.0	O2—C12—H12C	109.5
C5—C6—C1	118.93 (7)	H12A—C12—H12C	109.5
C5—C6—C7	118.62 (7)	H12B—C12—H12C	109.5
O1i—Pd1—O1—C1	−132.69 (5)	C3—C4—C5—C6	1.59 (13)
N1—Pd1—O1—C1	43.75 (6)	C4—C5—C6—C1	−3.42 (13)
O1—Pd1—N1—C7	−29.00 (6)	C4—C5—C6—C7	178.41 (8)
N1i—Pd1—N1—C7	147.14 (5)	O1—C1—C6—C5	−177.99 (7)
O1—Pd1—N1—C8	153.13 (6)	C2—C1—C6—C5	1.59 (11)
N1i—Pd1—N1—C8	−30.72 (7)	O1—C1—C6—C7	0.11 (12)
Pd1—O1—C1—C2	144.53 (6)	C2—C1—C6—C7	179.69 (7)
Pd1—O1—C1—C6	−35.88 (10)	C8—N1—C7—C6	−176.76 (8)
O1—C1—C2—C3	−178.41 (7)	Pd1—N1—C7—C6	5.33 (11)
C6—C1—C2—C3	1.98 (11)	C5—C6—C7—N1	−164.51 (8)
C12—O2—C3—C2	−6.96 (12)	C1—C6—C7—N1	17.38 (13)
C12—O2—C3—C4	171.91 (8)	C7—N1—C8—C9	−125.73 (8)
C1—C2—C3—O2	174.91 (7)	Pd1—N1—C8—C9	52.19 (9)
C1—C2—C3—C4	−3.90 (12)	N1—C8—C9—C10	57.06 (10)
O2—C3—C4—C5	−176.79 (8)	N1—C8—C9—C8i	−67.56 (11)
C2—C3—C4—C5	2.11 (13)	N1—C8—C9—C11	177.01 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ii	0.99	2.37	3.3355 (10)	166
C12—H12A···O2iii	0.98	2.58	3.3719 (12)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.99	2.37	3.3355 (10)	166
C12—H12A⋯O2ii	0.98	2.58	3.3719 (12)	138

Symmetry codes: (i) ; (ii) .