Bis{2-meth-oxy-6-[(E)-(4-methyl-benz-yl)imino-meth-yl]phenolato}palladium(II) chloro-form monosolvate.

In the title complex, [Pd(C16H16NO2)2]·CHCl3, the Pd(II) cation lies on an inversion center. One Cl atom of the CHCl3 solvent mol-ecule lies on a twofold axis and the C-H group is disordered with equal occupancies about this axis with the other Cl atom in a general position with full occupancy. The Pd(II) cation is four-coordinate and adopts a square-planar geometry via coordination of the imine N and phenolic O atoms of the two bidentate Schiff base anions. The N and O atoms of these ligands are mutually trans. The plane of the benzene ring makes a dihedral angle of 73.52 (10)° with that of the meth-oxy-phenolate ring. In the crystal, mol-ecules of the Pd(II) complex are arranged into sheets parallel to the ac plane, and the chloro-form solvent mol-ecules are located in the inter-stitial areas between the complex mol-ecules. Weak inter-molecular C-H⋯O and C-H⋯π inter-actions stabilize the packing.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Bahron et al. (2011 ▶); Halder et al. (2008 ▶). For background to and applications of PdII complexes, see: Bowes et al. (2011 ▶); Geeta et al. (2010 ▶); Gupta & Sutar (2008 ▶); Kalita et al. (2014 ▶); Mohd Tajuddin et al. (2012 ▶); Tamizh & Karvembu (2012 ▶).

Experimental

Crystal data

[Pd(C16H16NO2)2]·CHCl3

M = 734.36

Monoclinic,

a = 31.9861 (8) Å

b = 5.9668 (2) Å

c = 22.6135 (5) Å

β = 134.885 (1)°

V = 3057.92 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.91 mm−1

T = 100 K

0.48 × 0.25 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.669, T max = 0.853

43800 measured reflections

5542 independent reflections

5006 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.073

S = 1.05

5542 reflections

204 parameters

H-atom parameters constrained

Δρmax = 1.24 e Å−3

Δρmin = −1.90 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, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814015025/sj5416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015025/sj5416Isup2.hkl

CCDC reference: 1010352

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Pd(C16H16NO)2]·CHCl3	F(000) = 1496
Mr = 734.36	Dx = 1.595 Mg m−3
Monoclinic, C2/c	Melting point = 509–511 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 31.9861 (8) Å	Cell parameters from 5542 reflections
b = 5.9668 (2) Å	θ = 1.8–32.5°
c = 22.6135 (5) Å	µ = 0.91 mm−1
β = 134.885 (1)°	T = 100 K
V = 3057.92 (15) Å3	Block, orange
Z = 4	0.48 × 0.25 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	5542 independent reflections
Radiation source: sealed tube	5006 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 32.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −48→48
Tmin = 0.669, Tmax = 0.853	k = −9→8
43800 measured reflections	l = −33→34

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.029P)2 + 8.064P] where P = (Fo2 + 2Fc2)/3
5542 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 1.24 e Å−3
0 restraints	Δρmin = −1.90 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	Occ. (<1)
Pd1	0.2500	0.7500	0.5000	0.01355 (4)
O1	0.27424 (5)	0.77360 (19)	0.44058 (7)	0.0199 (2)
O2	0.29036 (5)	0.7333 (2)	0.34385 (7)	0.0216 (2)
N1	0.29650 (5)	1.0260 (2)	0.56892 (7)	0.0161 (2)
C1	0.30562 (6)	0.9327 (2)	0.44764 (8)	0.0163 (2)
C2	0.31517 (6)	0.9175 (3)	0.39460 (9)	0.0182 (2)
C3	0.34628 (7)	1.0811 (3)	0.39600 (9)	0.0230 (3)
H3A	0.3517	1.0693	0.3607	0.028*
C4	0.36987 (8)	1.2650 (3)	0.44999 (10)	0.0256 (3)
H4A	0.3909	1.3743	0.4505	0.031*
C5	0.36196 (7)	1.2838 (3)	0.50202 (10)	0.0229 (3)
H5A	0.3777	1.4061	0.5378	0.028*
C6	0.32999 (6)	1.1187 (2)	0.50177 (8)	0.0172 (2)
C7	0.32398 (6)	1.1514 (2)	0.55844 (9)	0.0176 (2)
H7A	0.3421	1.2786	0.5918	0.021*
C8	0.30159 (6)	1.0981 (3)	0.63693 (9)	0.0180 (2)
H8A	0.2676	1.0451	0.6249	0.022*
H8B	0.3020	1.2605	0.6393	0.022*
C9	0.35728 (6)	1.0068 (2)	0.72040 (9)	0.0169 (2)
C10	0.40868 (7)	1.1352 (3)	0.77237 (9)	0.0215 (3)
H10A	0.4083	1.2778	0.7555	0.026*
C11	0.46054 (7)	1.0533 (3)	0.84920 (10)	0.0245 (3)
H11A	0.4943	1.1418	0.8829	0.029*
C12	0.46238 (7)	0.8403 (3)	0.87610 (9)	0.0220 (3)
C13	0.41100 (7)	0.7121 (3)	0.82397 (10)	0.0213 (3)
H13A	0.4114	0.5695	0.8409	0.026*
C14	0.35894 (7)	0.7929 (3)	0.74686 (9)	0.0197 (3)
H14A	0.3253	0.7038	0.7130	0.024*
C15	0.30447 (7)	0.6982 (3)	0.29710 (10)	0.0257 (3)
H15A	0.2903	0.5538	0.2708	0.039*
H15B	0.3465	0.7047	0.3339	0.039*
H15C	0.2861	0.8125	0.2552	0.039*
C16	0.51830 (8)	0.7502 (3)	0.95912 (11)	0.0325 (4)
H16A	0.5514	0.7914	0.9680	0.049*
H16B	0.5160	0.5899	0.9593	0.049*
H16C	0.5232	0.8119	1.0029	0.049*
C17	0.00983 (14)	0.8371 (6)	0.2433 (2)	0.0230 (6)	0.50
H17A	0.0259	0.8362	0.2200	0.028*	0.50
Cl1	0.0000	1.12294 (11)	0.2500	0.04186 (16)
Cl2	0.05936 (2)	0.70272 (10)	0.33308 (4)	0.04878 (16)

	U11	U22	U33	U12	U13	U23
Pd1	0.01277 (6)	0.01580 (7)	0.01323 (7)	−0.00043 (4)	0.00959 (6)	−0.00051 (4)
O1	0.0230 (5)	0.0231 (5)	0.0223 (5)	−0.0064 (4)	0.0191 (5)	−0.0050 (4)
O2	0.0230 (5)	0.0280 (6)	0.0217 (5)	−0.0055 (4)	0.0185 (5)	−0.0047 (4)
N1	0.0145 (5)	0.0181 (5)	0.0143 (5)	0.0009 (4)	0.0097 (4)	−0.0003 (4)
C1	0.0133 (5)	0.0203 (6)	0.0138 (5)	0.0002 (4)	0.0090 (5)	0.0020 (4)
C2	0.0144 (5)	0.0243 (7)	0.0141 (5)	−0.0012 (5)	0.0095 (5)	0.0014 (5)
C3	0.0205 (6)	0.0314 (8)	0.0182 (6)	−0.0042 (6)	0.0141 (6)	0.0022 (6)
C4	0.0247 (7)	0.0297 (8)	0.0210 (7)	−0.0081 (6)	0.0156 (6)	0.0016 (6)
C5	0.0213 (7)	0.0251 (7)	0.0179 (6)	−0.0064 (5)	0.0122 (6)	−0.0005 (5)
C6	0.0144 (5)	0.0200 (6)	0.0132 (5)	−0.0006 (5)	0.0083 (5)	0.0019 (5)
C7	0.0152 (5)	0.0179 (6)	0.0147 (5)	−0.0001 (5)	0.0088 (5)	0.0001 (4)
C8	0.0182 (6)	0.0192 (6)	0.0181 (6)	0.0007 (5)	0.0134 (5)	−0.0023 (5)
C9	0.0177 (6)	0.0191 (6)	0.0159 (5)	−0.0001 (5)	0.0126 (5)	−0.0029 (5)
C10	0.0219 (6)	0.0203 (6)	0.0191 (6)	−0.0032 (5)	0.0134 (6)	−0.0033 (5)
C11	0.0206 (6)	0.0264 (7)	0.0186 (6)	−0.0046 (6)	0.0111 (6)	−0.0043 (5)
C12	0.0207 (6)	0.0271 (7)	0.0173 (6)	0.0025 (5)	0.0131 (6)	−0.0005 (5)
C13	0.0235 (7)	0.0220 (6)	0.0213 (6)	0.0017 (5)	0.0168 (6)	0.0008 (5)
C14	0.0197 (6)	0.0223 (6)	0.0192 (6)	−0.0014 (5)	0.0145 (6)	−0.0016 (5)
C15	0.0249 (7)	0.0374 (9)	0.0234 (7)	−0.0029 (6)	0.0202 (6)	−0.0036 (6)
C16	0.0251 (8)	0.0385 (10)	0.0215 (7)	0.0054 (7)	0.0120 (7)	0.0050 (7)
C17	0.0241 (14)	0.0232 (14)	0.0245 (14)	−0.0037 (11)	0.0181 (12)	−0.0041 (11)
Cl1	0.0565 (4)	0.0199 (3)	0.0593 (5)	0.000	0.0445 (4)	0.000
Cl2	0.0256 (2)	0.0353 (2)	0.0438 (3)	0.00892 (18)	0.0097 (2)	−0.0081 (2)

Pd1—O1i	1.9741 (10)	C9—C14	1.395 (2)
Pd1—O1	1.9741 (10)	C10—C11	1.393 (2)
Pd1—N1	2.0204 (12)	C10—H10A	0.9300
Pd1—N1i	2.0204 (12)	C11—C12	1.392 (2)
O1—C1	1.3069 (17)	C11—H11A	0.9300
O2—C2	1.3672 (19)	C12—C13	1.393 (2)
O2—C15	1.4279 (18)	C12—C16	1.508 (2)
N1—C7	1.2971 (19)	C13—C14	1.396 (2)
N1—C8	1.4911 (18)	C13—H13A	0.9300
C1—C6	1.411 (2)	C14—H14A	0.9300
C1—C2	1.4344 (19)	C15—H15A	0.9600
C2—C3	1.378 (2)	C15—H15B	0.9600
C3—C4	1.401 (2)	C15—H15C	0.9600
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.372 (2)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.417 (2)	C17—C17ii	0.871 (6)
C5—H5A	0.9300	C17—Cl2	1.654 (3)
C6—C7	1.437 (2)	C17—Cl1	1.760 (3)
C7—H7A	0.9300	C17—Cl2ii	1.769 (3)
C8—C9	1.512 (2)	C17—H17A	0.9604
C8—H8A	0.9700	Cl1—C17ii	1.760 (3)
C8—H8B	0.9700	Cl2—C17ii	1.769 (3)
C9—C10	1.394 (2)
O1i—Pd1—O1	180.000 (1)	C10—C9—C8	120.25 (14)
O1i—Pd1—N1	87.83 (5)	C14—C9—C8	121.32 (13)
O1—Pd1—N1	92.17 (5)	C11—C10—C9	121.09 (15)
O1i—Pd1—N1i	92.17 (5)	C11—C10—H10A	119.5
O1—Pd1—N1i	87.83 (5)	C9—C10—H10A	119.5
N1—Pd1—N1i	180.0	C12—C11—C10	120.73 (15)
C1—O1—Pd1	127.25 (9)	C12—C11—H11A	119.6
C2—O2—C15	116.10 (12)	C10—C11—H11A	119.6
C7—N1—C8	115.30 (12)	C11—C12—C13	118.08 (14)
C7—N1—Pd1	123.66 (10)	C11—C12—C16	121.11 (16)
C8—N1—Pd1	121.04 (9)	C13—C12—C16	120.82 (16)
O1—C1—C6	125.72 (13)	C12—C13—C14	121.50 (15)
O1—C1—C2	116.75 (13)	C12—C13—H13A	119.2
C6—C1—C2	117.52 (13)	C14—C13—H13A	119.2
O2—C2—C3	124.80 (13)	C9—C14—C13	120.18 (14)
O2—C2—C1	114.39 (12)	C9—C14—H14A	119.9
C3—C2—C1	120.81 (14)	C13—C14—H14A	119.9
C2—C3—C4	120.72 (14)	O2—C15—H15A	109.5
C2—C3—H3A	119.6	O2—C15—H15B	109.5
C4—C3—H3A	119.6	H15A—C15—H15B	109.5
C5—C4—C3	119.97 (15)	O2—C15—H15C	109.5
C5—C4—H4A	120.0	H15A—C15—H15C	109.5
C3—C4—H4A	120.0	H15B—C15—H15C	109.5
C4—C5—C6	120.60 (15)	C12—C16—H16A	109.5
C4—C5—H5A	119.7	C12—C16—H16B	109.5
C6—C5—H5A	119.7	H16A—C16—H16B	109.5
C1—C6—C5	120.37 (13)	C12—C16—H16C	109.5
C1—C6—C7	122.75 (13)	H16A—C16—H16C	109.5
C5—C6—C7	116.89 (14)	H16B—C16—H16C	109.5
N1—C7—C6	128.23 (14)	C17ii—C17—Cl2	82.7 (4)
N1—C7—H7A	115.9	C17ii—C17—Cl1	75.67 (10)
C6—C7—H7A	115.9	Cl2—C17—Cl1	115.99 (18)
N1—C8—C9	111.02 (11)	C17ii—C17—Cl2ii	68.1 (4)
N1—C8—H8A	109.4	Cl2—C17—Cl2ii	115.65 (19)
C9—C8—H8A	109.4	Cl1—C17—Cl2ii	110.29 (18)
N1—C8—H8B	109.4	C17ii—C17—H17A	171.5
C9—C8—H8B	109.4	Cl2—C17—H17A	104.5
H8A—C8—H8B	108.0	Cl1—C17—H17A	104.5
C10—C9—C14	118.42 (14)	Cl2ii—C17—H17A	104.4
N1—Pd1—O1—C1	−4.24 (13)	C4—C5—C6—C7	179.83 (15)
N1i—Pd1—O1—C1	175.76 (13)	C8—N1—C7—C6	176.22 (13)
O1i—Pd1—N1—C7	−175.14 (12)	Pd1—N1—C7—C6	−3.4 (2)
O1—Pd1—N1—C7	4.86 (12)	C1—C6—C7—N1	−0.7 (2)
O1i—Pd1—N1—C8	5.26 (10)	C5—C6—C7—N1	179.23 (15)
O1—Pd1—N1—C8	−174.74 (10)	C7—N1—C8—C9	−85.20 (15)
Pd1—O1—C1—C6	1.8 (2)	Pd1—N1—C8—C9	94.43 (13)
Pd1—O1—C1—C2	−177.17 (10)	N1—C8—C9—C10	93.72 (16)
C15—O2—C2—C3	7.9 (2)	N1—C8—C9—C14	−85.35 (16)
C15—O2—C2—C1	−173.07 (13)	C14—C9—C10—C11	−0.4 (2)
O1—C1—C2—O2	−0.92 (19)	C8—C9—C10—C11	−179.47 (14)
C6—C1—C2—O2	180.00 (12)	C9—C10—C11—C12	0.1 (2)
O1—C1—C2—C3	178.12 (14)	C10—C11—C12—C13	0.1 (2)
C6—C1—C2—C3	−1.0 (2)	C10—C11—C12—C16	179.97 (16)
O2—C2—C3—C4	179.63 (15)	C11—C12—C13—C14	0.0 (2)
C1—C2—C3—C4	0.7 (2)	C16—C12—C13—C14	−179.83 (15)
C2—C3—C4—C5	−0.2 (3)	C10—C9—C14—C13	0.5 (2)
C3—C4—C5—C6	−0.1 (3)	C8—C9—C14—C13	179.60 (13)
O1—C1—C6—C5	−178.26 (14)	C12—C13—C14—C9	−0.3 (2)
C2—C1—C6—C5	0.7 (2)	Cl2—C17—Cl1—C17ii	−74.3 (4)
O1—C1—C6—C7	1.7 (2)	Cl2ii—C17—Cl1—C17ii	59.6 (4)
C2—C1—C6—C7	−179.34 (13)	Cl1—C17—Cl2—C17ii	70.1 (2)
C4—C5—C6—C1	−0.2 (2)	Cl2ii—C17—Cl2—C17ii	−61.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.97	2.19	2.806 (2)	120
C14—H14A···O1i	0.93	2.57	3.284 (2)	134
C17—H17A···Cg1i	0.96	2.83	3.648 (5)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.97	2.19	2.806 (2)	120
C14—H14A⋯O1i	0.93	2.57	3.284 (2)	134
C17—H17A⋯Cg1i	0.96	2.83	3.648 (5)	144

Symmetry code: (i) .