Bis[3,3-dimethyl-2-(2-oxoethyl­idene)indolinyl-κ2N,O]palladium(II)

Khaledi, H.; Olmstead, M.M.; Mohd Ali, H.

doi:10.1107/S1600536811022069

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m929

doi:10.1107/S1600536811022069

Open

access

Bis[3,3-dimethyl-2-(2-oxoethylidene)indolinyl-κ²N,O]palladium(II)

Hamid Khaledi,^a ^* Marilyn M. Olmstead ^b and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Chemistry, University of California, One Shields Avenue, Davis, CA, 95616, USA.
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 20 May 2011; accepted 7 June 2011; online 18 June 2011)

The asymmetric unit of the title compound, [Pd(C₁₂H₁₂NO)₂], consists of three crystallographically independent half-molecules. Each Pd^II atom lies on a center of inversion and is four-coordinated by two monoanionic forms of the aminoacrylaldehyde in a square-planar geometry. In the crystal, adjacent molecules are connected through C—H⋯π and C—H⋯O interactions into a three-dimensional polymeric structure.

Related literature

For the structures of related compounds, see: Khaledi et al. (2011 ).

Experimental

Crystal data

[Pd(C₁₂H₁₂NO)₂]
M_r = 478.85
Triclinic, $[P \overline 1]$
a = 10.453 (2) Å
b = 12.669 (3) Å
c = 13.056 (3) Å
α = 87.750 (3)°
β = 73.271 (3)°
γ = 70.565 (3)°
V = 1558.5 (6) Å³
Z = 3
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 100 K
0.18 × 0.09 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.853, T_max = 0.947
13381 measured reflections
6083 independent reflections
4905 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.095
S = 1.03
6083 reflections
403 parameters
H-atom parameters constrained
Δρ_max = 1.35 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the benzene C27–C32 and C3–C8 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.95	2.40	3.353 (5)	177
C7—H7⋯O1ⁱⁱ	0.95	2.34	2.965 (4)	123
C19—H19⋯O2ⁱ	0.95	2.27	2.860 (5)	120
C31—H31⋯O3ⁱⁱⁱ	0.95	2.25	2.861 (5)	121
C9—H9⋯Cg1^iv	0.95	2.85	3.794 (5)	170
C33—H33⋯Cg2ⁱ	0.95	2.76	3.630 (4)	153
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y, -z; (iii) -x+1, -y+2, -z+1; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811022069/is2718sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022069/is2718Isup2.hkl

checkCIF report

Comment top

We have recently reported the reaction of 2-(diformylmethylidene)-3,3-dimethylindole, I, (Fig. 2), with palladium(II) ion to produce the complex II (Khaledi et al., 2011). As was reported, further recrystallization of the obtained N₂O₂-coordinated Pd^II complex from a mixture of DMF and pyridine led to the formation of acyl-palladium complexes III & IV. We were surprised to discover that leaving the recrystallization solution at room temperature for a longer time gave rise to slow disappearance of crystals of III & IV and formation of the orange crystals of the title compound. Herein, we report the crystal structure of the obtained Pd^II complex.

The crystal structure is composed of three square planar centrosymmetric complexes. In each molecule, two monoanionic ligands chelate the Pd^II ion in an N,O-mode to form two six-membered rings with the metal atom. The O—Pd—N bite angles are 90.38 (11), 90.13 (11) and 91.08 (11)° for the complexes of Pd1, Pd2 and Pd3, respectively. The three complexes have little difference in their geometries, but differ more in their intermolecular interactions. The Pd1 and Pd3 complexes are connected through C—H···π interactions (Table 1), forming infinite layers parallel to the ac plane. The layers are further linked into a three dimensional network via C—H···O hydrogen bonds (Table 1) formed between Pd1 and Pd2 molecules. Intramolecular C—H···O hydrogen bonding occurs in all three complexes.

Related literature top

For the structures of the related compounds, see: Khaledi et al. (2011).

Experimental top

A solution of palladium(II) complex II (Fig. 2) in a mixture of DMF and pyridine yielded the yellowish green crystals of III and IV in two weeks. Upon standing of the solution in a closed vial at room temperature for a month, the orange crystals of the title compound appeared while the former crystals began to disappear slowly and finally disappeared completely after two months.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound (50% probability ellipsoids). Hydrogen atoms have been omitted for clarity. Symmetry codes: ' = -x, -y, -z; '' = -x, -y+1, -z+1; ''' = -x+1, -y+2, -z+1.
	Fig. 2. Reaction scheme.

Bis[3,3-dimethyl-2-(2-oxoethylidene)indolinyl- κ²N,O]palladium(II) top

Crystal data top

[Pd(C₁₂H₁₂NO)₂]	Z = 3
M_r = 478.85	F(000) = 732
Triclinic, P1	D_x = 1.531 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.453 (2) Å	Cell parameters from 2716 reflections
b = 12.669 (3) Å	θ = 2.3–24.8°
c = 13.056 (3) Å	µ = 0.92 mm⁻¹
α = 87.750 (3)°	T = 100 K
β = 73.271 (3)°	Rod, orange
γ = 70.565 (3)°	0.18 × 0.09 × 0.06 mm
V = 1558.5 (6) Å³

Data collection top

Bruker APEXII CCD diffractometer	6083 independent reflections
Radiation source: fine-focus sealed tube	4905 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.853, T_max = 0.947	k = −15→15
13381 measured reflections	l = −16→16

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.042P)²] where P = (F_o² + 2F_c²)/3
6083 reflections	(Δ/σ)_max < 0.001
403 parameters	Δρ_max = 1.35 e Å⁻³
0 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

[Pd(C₁₂H₁₂NO)₂]	γ = 70.565 (3)°
M_r = 478.85	V = 1558.5 (6) Å³
Triclinic, P1	Z = 3
a = 10.453 (2) Å	Mo Kα radiation
b = 12.669 (3) Å	µ = 0.92 mm⁻¹
c = 13.056 (3) Å	T = 100 K
α = 87.750 (3)°	0.18 × 0.09 × 0.06 mm
β = 73.271 (3)°

Data collection top

Bruker APEXII CCD diffractometer	6083 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4905 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.947	R_int = 0.042
13381 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.03	Δρ_max = 1.35 e Å⁻³
6083 reflections	Δρ_min = −0.75 e Å⁻³
403 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

	x	y	z	U_iso*/U_eq
Pd1	0.0000	0.0000	0.0000	0.01805 (11)
O1	0.2061 (3)	−0.0799 (2)	−0.0656 (2)	0.0239 (6)
N1	0.0435 (3)	0.0856 (2)	0.1068 (2)	0.0179 (7)
C1	0.1611 (4)	0.0445 (3)	0.1357 (3)	0.0202 (8)
C2	0.1613 (4)	0.1157 (3)	0.2271 (3)	0.0190 (8)
C3	0.0286 (4)	0.2125 (3)	0.2365 (3)	0.0190 (8)
C4	−0.0276 (4)	0.3108 (3)	0.2998 (3)	0.0212 (9)
H4	0.0172	0.3235	0.3497	0.025*
C5	−0.1499 (4)	0.3907 (3)	0.2897 (3)	0.0229 (9)
H5	−0.1900	0.4589	0.3329	0.027*
C6	−0.2146 (4)	0.3718 (3)	0.2166 (3)	0.0214 (9)
H6	−0.2977	0.4280	0.2092	0.026*
C7	−0.1596 (4)	0.2716 (3)	0.1537 (3)	0.0185 (8)
H7	−0.2050	0.2585	0.1045	0.022*
C8	−0.0379 (4)	0.1920 (3)	0.1645 (3)	0.0156 (8)
C9	0.2790 (4)	−0.0489 (3)	0.0843 (3)	0.0261 (9)
H9	0.3503	−0.0801	0.1191	0.031*
C10	0.2965 (4)	−0.0971 (3)	−0.0124 (3)	0.0272 (10)
H10	0.3874	−0.1504	−0.0448	0.033*
C11	0.2927 (4)	0.1515 (3)	0.2003 (4)	0.0285 (10)
H11A	0.2987	0.1924	0.1348	0.043*
H11B	0.3778	0.0848	0.1893	0.043*
H11C	0.2859	0.2001	0.2596	0.043*
C12	0.1514 (5)	0.0497 (4)	0.3293 (3)	0.0293 (10)
H12A	0.1449	0.0972	0.3893	0.044*
H12B	0.2362	−0.0173	0.3176	0.044*
H12C	0.0669	0.0272	0.3457	0.044*
Pd2	0.0000	0.5000	0.5000	0.01294 (11)
O2	−0.1393 (3)	0.6550 (2)	0.52634 (19)	0.0188 (6)
N2	0.0867 (3)	0.5334 (3)	0.3486 (2)	0.0159 (7)
C13	0.0131 (4)	0.6108 (3)	0.2965 (3)	0.0193 (8)
C14	0.0925 (4)	0.6054 (3)	0.1789 (3)	0.0235 (9)
C15	0.2302 (4)	0.5152 (3)	0.1742 (3)	0.0230 (9)
C16	0.3528 (5)	0.4708 (4)	0.0914 (3)	0.0310 (11)
H16	0.3586	0.4957	0.0211	0.037*
C17	0.4673 (5)	0.3894 (4)	0.1122 (4)	0.0350 (11)
H17	0.5513	0.3564	0.0552	0.042*
C18	0.4609 (4)	0.3559 (3)	0.2136 (4)	0.0301 (10)
H18	0.5417	0.3014	0.2264	0.036*
C19	0.3392 (4)	0.3996 (3)	0.2981 (3)	0.0214 (9)
H19	0.3357	0.3768	0.3688	0.026*
C20	0.2232 (4)	0.4774 (3)	0.2763 (3)	0.0188 (8)
C21	−0.1195 (4)	0.6926 (3)	0.3431 (3)	0.0253 (9)
H21	−0.1702	0.7359	0.2973	0.030*
C22	−0.1785 (4)	0.7127 (3)	0.4509 (3)	0.0248 (9)
H22	−0.2596	0.7783	0.4734	0.030*
C23	0.1133 (5)	0.7192 (4)	0.1471 (3)	0.0328 (11)
H23A	0.1568	0.7420	0.1957	0.049*
H23B	0.0210	0.7762	0.1521	0.049*
H23C	0.1752	0.7112	0.0734	0.049*
C24	0.0148 (5)	0.5727 (4)	0.1081 (3)	0.0373 (12)
H24A	0.0701	0.5674	0.0326	0.056*
H24B	−0.0789	0.6300	0.1189	0.056*
H24C	0.0037	0.5002	0.1277	0.056*
Pd3	0.5000	1.0000	0.5000	0.01505 (11)
O3	0.3211 (3)	1.0191 (2)	0.6163 (2)	0.0218 (6)
N3	0.4648 (3)	0.8844 (2)	0.4194 (2)	0.0171 (7)
C25	0.3843 (4)	0.8253 (3)	0.4695 (3)	0.0170 (8)
C26	0.3941 (4)	0.7294 (3)	0.3976 (3)	0.0210 (9)
C27	0.4854 (4)	0.7514 (3)	0.2935 (3)	0.0205 (9)
C28	0.5324 (5)	0.6965 (3)	0.1924 (3)	0.0267 (10)
H28	0.5075	0.6331	0.1816	0.032*
C29	0.6159 (5)	0.7355 (4)	0.1080 (3)	0.0310 (10)
H29	0.6506	0.6978	0.0390	0.037*
C30	0.6491 (4)	0.8297 (4)	0.1241 (3)	0.0277 (10)
H30	0.7044	0.8568	0.0650	0.033*
C31	0.6035 (4)	0.8854 (3)	0.2245 (3)	0.0218 (9)
H31	0.6264	0.9500	0.2346	0.026*
C32	0.5235 (4)	0.8437 (3)	0.3091 (3)	0.0181 (8)
C33	0.2959 (4)	0.8471 (3)	0.5760 (3)	0.0228 (9)
H33	0.2549	0.7924	0.6067	0.027*
C34	0.2652 (4)	0.9417 (3)	0.6379 (3)	0.0253 (9)
H34	0.1943	0.9513	0.7048	0.030*
C35	0.2477 (4)	0.7321 (4)	0.3930 (3)	0.0271 (10)
H35A	0.1988	0.8047	0.3691	0.041*
H35B	0.1914	0.7216	0.4644	0.041*
H35C	0.2595	0.6719	0.3426	0.041*
C36	0.4685 (5)	0.6181 (3)	0.4390 (3)	0.0288 (10)
H36A	0.4821	0.5561	0.3900	0.043*
H36B	0.4102	0.6096	0.5104	0.043*
H36C	0.5609	0.6173	0.4432	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0179 (2)	0.0176 (2)	0.0192 (2)	−0.00839 (18)	−0.00271 (18)	−0.00333 (17)
O1	0.0185 (14)	0.0241 (15)	0.0265 (15)	−0.0085 (12)	0.0006 (12)	−0.0092 (12)
N1	0.0220 (17)	0.0140 (16)	0.0178 (16)	−0.0082 (14)	−0.0034 (14)	0.0003 (13)
C1	0.022 (2)	0.016 (2)	0.027 (2)	−0.0102 (17)	−0.0078 (18)	0.0025 (17)
C2	0.021 (2)	0.020 (2)	0.021 (2)	−0.0119 (17)	−0.0078 (17)	0.0004 (16)
C3	0.019 (2)	0.0149 (19)	0.024 (2)	−0.0069 (16)	−0.0056 (17)	0.0017 (16)
C4	0.024 (2)	0.022 (2)	0.021 (2)	−0.0137 (18)	−0.0065 (17)	−0.0036 (17)
C5	0.030 (2)	0.018 (2)	0.022 (2)	−0.0134 (18)	−0.0019 (18)	−0.0021 (17)
C6	0.023 (2)	0.0128 (19)	0.027 (2)	−0.0051 (17)	−0.0063 (18)	0.0028 (17)
C7	0.023 (2)	0.020 (2)	0.0153 (19)	−0.0124 (17)	−0.0038 (16)	0.0035 (16)
C8	0.020 (2)	0.0148 (19)	0.0134 (18)	−0.0104 (16)	−0.0004 (16)	0.0002 (15)
C9	0.023 (2)	0.021 (2)	0.039 (3)	−0.0107 (18)	−0.013 (2)	0.0015 (19)
C10	0.017 (2)	0.020 (2)	0.044 (3)	−0.0069 (18)	−0.005 (2)	−0.0080 (19)
C11	0.021 (2)	0.028 (2)	0.042 (3)	−0.0128 (19)	−0.012 (2)	0.000 (2)
C12	0.033 (2)	0.029 (2)	0.030 (2)	−0.010 (2)	−0.018 (2)	0.0124 (19)
Pd2	0.0149 (2)	0.0131 (2)	0.0107 (2)	−0.00434 (17)	−0.00404 (16)	0.00026 (15)
O2	0.0198 (14)	0.0162 (14)	0.0180 (14)	−0.0028 (11)	−0.0060 (11)	0.0018 (11)
N2	0.0183 (17)	0.0186 (17)	0.0125 (15)	−0.0080 (14)	−0.0049 (13)	0.0009 (13)
C13	0.024 (2)	0.026 (2)	0.0143 (19)	−0.0140 (18)	−0.0089 (17)	0.0046 (16)
C14	0.033 (2)	0.036 (2)	0.0104 (18)	−0.023 (2)	−0.0078 (17)	0.0071 (17)
C15	0.030 (2)	0.026 (2)	0.019 (2)	−0.0220 (19)	−0.0021 (18)	−0.0027 (17)
C16	0.045 (3)	0.035 (3)	0.016 (2)	−0.029 (2)	0.007 (2)	−0.0068 (19)
C17	0.031 (3)	0.024 (2)	0.042 (3)	−0.016 (2)	0.013 (2)	−0.010 (2)
C18	0.023 (2)	0.023 (2)	0.043 (3)	−0.0139 (19)	0.000 (2)	−0.002 (2)
C19	0.021 (2)	0.018 (2)	0.027 (2)	−0.0114 (17)	−0.0031 (18)	0.0005 (17)
C20	0.022 (2)	0.021 (2)	0.0172 (19)	−0.0156 (18)	−0.0006 (16)	−0.0042 (16)
C21	0.027 (2)	0.025 (2)	0.025 (2)	−0.0058 (19)	−0.0139 (19)	0.0110 (18)
C22	0.020 (2)	0.017 (2)	0.031 (2)	0.0026 (17)	−0.0089 (19)	0.0024 (18)
C23	0.049 (3)	0.036 (3)	0.023 (2)	−0.026 (2)	−0.013 (2)	0.014 (2)
C24	0.052 (3)	0.059 (3)	0.021 (2)	−0.037 (3)	−0.021 (2)	0.013 (2)
Pd3	0.0166 (2)	0.0113 (2)	0.0193 (2)	−0.00579 (17)	−0.00698 (17)	0.00068 (16)
O3	0.0213 (15)	0.0200 (15)	0.0245 (15)	−0.0110 (12)	−0.0020 (12)	−0.0023 (12)
N3	0.0196 (17)	0.0142 (16)	0.0197 (16)	−0.0063 (14)	−0.0083 (14)	0.0016 (13)
C25	0.020 (2)	0.0133 (19)	0.021 (2)	−0.0072 (16)	−0.0090 (17)	0.0022 (16)
C26	0.029 (2)	0.014 (2)	0.024 (2)	−0.0088 (17)	−0.0106 (18)	0.0022 (16)
C27	0.027 (2)	0.0103 (19)	0.025 (2)	−0.0031 (17)	−0.0137 (18)	0.0014 (16)
C28	0.037 (3)	0.017 (2)	0.030 (2)	−0.0087 (19)	−0.015 (2)	−0.0028 (18)
C29	0.043 (3)	0.030 (2)	0.024 (2)	−0.012 (2)	−0.015 (2)	0.0016 (19)
C30	0.028 (2)	0.032 (2)	0.021 (2)	−0.007 (2)	−0.0073 (19)	0.0017 (19)
C31	0.025 (2)	0.017 (2)	0.026 (2)	−0.0091 (18)	−0.0093 (18)	0.0017 (17)
C32	0.020 (2)	0.017 (2)	0.020 (2)	−0.0031 (16)	−0.0123 (17)	0.0001 (16)
C33	0.028 (2)	0.018 (2)	0.027 (2)	−0.0143 (18)	−0.0076 (18)	0.0064 (17)
C34	0.023 (2)	0.029 (2)	0.022 (2)	−0.0137 (19)	0.0017 (18)	0.0004 (18)
C35	0.030 (2)	0.029 (2)	0.033 (2)	−0.019 (2)	−0.015 (2)	0.0028 (19)
C36	0.040 (3)	0.013 (2)	0.035 (2)	−0.0062 (19)	−0.017 (2)	0.0040 (18)

Geometric parameters (Å, º) top

Pd1—O1ⁱ	1.989 (3)	C17—C18	1.364 (6)
Pd1—O1	1.989 (3)	C17—H17	0.9500
Pd1—N1ⁱ	2.035 (3)	C18—C19	1.384 (5)
Pd1—N1	2.035 (3)	C18—H18	0.9500
O1—C10	1.285 (5)	C19—C20	1.381 (5)
N1—C1	1.323 (5)	C19—H19	0.9500
N1—C8	1.434 (4)	C21—C22	1.359 (5)
C1—C9	1.410 (5)	C21—H21	0.9500
C1—C2	1.524 (5)	C22—H22	0.9500
C2—C3	1.491 (5)	C23—H23A	0.9800
C2—C11	1.530 (5)	C23—H23B	0.9800
C2—C12	1.543 (5)	C23—H23C	0.9800
C3—C4	1.377 (5)	C24—H24A	0.9800
C3—C8	1.397 (5)	C24—H24B	0.9800
C4—C5	1.379 (5)	C24—H24C	0.9800
C4—H4	0.9500	Pd3—O3ⁱⁱⁱ	1.988 (3)
C5—C6	1.387 (5)	Pd3—O3	1.988 (3)
C5—H5	0.9500	Pd3—N3	2.022 (3)
C6—C7	1.393 (5)	Pd3—N3ⁱⁱⁱ	2.022 (3)
C6—H6	0.9500	O3—C34	1.284 (4)
C7—C8	1.375 (5)	N3—C25	1.327 (5)
C7—H7	0.9500	N3—C32	1.433 (5)
C9—C10	1.361 (5)	C25—C33	1.408 (5)
C9—H9	0.9500	C25—C26	1.524 (5)
C10—H10	0.9500	C26—C27	1.495 (5)
C11—H11A	0.9800	C26—C36	1.529 (5)
C11—H11B	0.9800	C26—C35	1.537 (5)
C11—H11C	0.9800	C27—C28	1.392 (5)
C12—H12A	0.9800	C27—C32	1.395 (5)
C12—H12B	0.9800	C28—C29	1.382 (6)
C12—H12C	0.9800	C28—H28	0.9500
Pd2—O2ⁱⁱ	1.989 (2)	C29—C30	1.387 (6)
Pd2—O2	1.989 (2)	C29—H29	0.9500
Pd2—N2ⁱⁱ	2.016 (3)	C30—C31	1.390 (5)
Pd2—N2	2.016 (3)	C30—H30	0.9500
O2—C22	1.285 (4)	C31—C32	1.383 (5)
N2—C13	1.328 (5)	C31—H31	0.9500
N2—C20	1.426 (5)	C33—C34	1.365 (5)
C13—C21	1.405 (5)	C33—H33	0.9500
C13—C14	1.512 (5)	C34—H34	0.9500
C14—C15	1.497 (6)	C35—H35A	0.9800
C14—C24	1.540 (5)	C35—H35B	0.9800
C14—C23	1.552 (5)	C35—H35C	0.9800
C15—C16	1.378 (5)	C36—H36A	0.9800
C15—C20	1.388 (5)	C36—H36B	0.9800
C16—C17	1.384 (6)	C36—H36C	0.9800
C16—H16	0.9500

O1ⁱ—Pd1—O1	180.00 (10)	C17—C18—C19	121.4 (4)
O1ⁱ—Pd1—N1ⁱ	90.38 (11)	C17—C18—H18	119.3
O1—Pd1—N1ⁱ	89.62 (11)	C19—C18—H18	119.3
O1ⁱ—Pd1—N1	89.62 (11)	C20—C19—C18	117.7 (4)
O1—Pd1—N1	90.38 (11)	C20—C19—H19	121.1
N1ⁱ—Pd1—N1	180.0	C18—C19—H19	121.1
C10—O1—Pd1	122.2 (3)	C19—C20—C15	121.3 (4)
C1—N1—C8	108.0 (3)	C19—C20—N2	128.4 (3)
C1—N1—Pd1	121.8 (2)	C15—C20—N2	110.3 (3)
C8—N1—Pd1	130.2 (2)	C22—C21—C13	123.0 (4)
N1—C1—C9	125.1 (4)	C22—C21—H21	118.5
N1—C1—C2	112.2 (3)	C13—C21—H21	118.5
C9—C1—C2	122.5 (3)	O2—C22—C21	128.7 (4)
C3—C2—C1	100.7 (3)	O2—C22—H22	115.6
C3—C2—C11	112.4 (3)	C21—C22—H22	115.6
C1—C2—C11	112.4 (3)	C14—C23—H23A	109.5
C3—C2—C12	111.7 (3)	C14—C23—H23B	109.5
C1—C2—C12	109.3 (3)	H23A—C23—H23B	109.5
C11—C2—C12	110.1 (3)	C14—C23—H23C	109.5
C4—C3—C8	121.0 (4)	H23A—C23—H23C	109.5
C4—C3—C2	130.2 (4)	H23B—C23—H23C	109.5
C8—C3—C2	108.8 (3)	C14—C24—H24A	109.5
C3—C4—C5	118.9 (4)	C14—C24—H24B	109.5
C3—C4—H4	120.5	H24A—C24—H24B	109.5
C5—C4—H4	120.5	C14—C24—H24C	109.5
C4—C5—C6	120.2 (4)	H24A—C24—H24C	109.5
C4—C5—H5	119.9	H24B—C24—H24C	109.5
C6—C5—H5	119.9	O3ⁱⁱⁱ—Pd3—O3	180.000 (1)
C5—C6—C7	121.0 (4)	O3ⁱⁱⁱ—Pd3—N3	88.92 (11)
C5—C6—H6	119.5	O3—Pd3—N3	91.08 (11)
C7—C6—H6	119.5	O3ⁱⁱⁱ—Pd3—N3ⁱⁱⁱ	91.08 (11)
C8—C7—C6	118.5 (3)	O3—Pd3—N3ⁱⁱⁱ	88.92 (11)
C8—C7—H7	120.7	N3—Pd3—N3ⁱⁱⁱ	179.999 (1)
C6—C7—H7	120.7	C34—O3—Pd3	122.8 (2)
C7—C8—C3	120.2 (3)	C25—N3—C32	108.0 (3)
C7—C8—N1	129.8 (3)	C25—N3—Pd3	121.4 (2)
C3—C8—N1	109.9 (3)	C32—N3—Pd3	130.4 (2)
C10—C9—C1	123.7 (4)	N3—C25—C33	125.6 (3)
C10—C9—H9	118.1	N3—C25—C26	112.3 (3)
C1—C9—H9	118.1	C33—C25—C26	122.1 (3)
O1—C10—C9	128.5 (4)	C27—C26—C25	100.5 (3)
O1—C10—H10	115.7	C27—C26—C36	111.4 (3)
C9—C10—H10	115.7	C25—C26—C36	108.9 (3)
C2—C11—H11A	109.5	C27—C26—C35	113.6 (3)
C2—C11—H11B	109.5	C25—C26—C35	112.3 (3)
H11A—C11—H11B	109.5	C36—C26—C35	109.7 (3)
C2—C11—H11C	109.5	C28—C27—C32	120.2 (4)
H11A—C11—H11C	109.5	C28—C27—C26	130.8 (4)
H11B—C11—H11C	109.5	C32—C27—C26	109.0 (3)
C2—C12—H12A	109.5	C29—C28—C27	119.1 (4)
C2—C12—H12B	109.5	C29—C28—H28	120.4
H12A—C12—H12B	109.5	C27—C28—H28	120.4
C2—C12—H12C	109.5	C28—C29—C30	120.0 (4)
H12A—C12—H12C	109.5	C28—C29—H29	120.0
H12B—C12—H12C	109.5	C30—C29—H29	120.0
O2ⁱⁱ—Pd2—O2	180.0	C29—C30—C31	121.7 (4)
O2ⁱⁱ—Pd2—N2ⁱⁱ	90.13 (11)	C29—C30—H30	119.1
O2—Pd2—N2ⁱⁱ	89.87 (11)	C31—C30—H30	119.1
O2ⁱⁱ—Pd2—N2	89.87 (11)	C32—C31—C30	117.8 (4)
O2—Pd2—N2	90.13 (11)	C32—C31—H31	121.1
N2ⁱⁱ—Pd2—N2	179.999 (1)	C30—C31—H31	121.1
C22—O2—Pd2	122.6 (2)	C31—C32—C27	121.1 (3)
C13—N2—C20	108.2 (3)	C31—C32—N3	129.0 (3)
C13—N2—Pd2	122.1 (2)	C27—C32—N3	109.9 (3)
C20—N2—Pd2	129.4 (2)	C34—C33—C25	124.3 (4)
N2—C13—C21	125.5 (3)	C34—C33—H33	117.8
N2—C13—C14	111.9 (3)	C25—C33—H33	117.8
C21—C13—C14	122.6 (3)	O3—C34—C33	127.6 (4)
C15—C14—C13	101.2 (3)	O3—C34—H34	116.2
C15—C14—C24	111.8 (3)	C33—C34—H34	116.2
C13—C14—C24	111.2 (3)	C26—C35—H35A	109.5
C15—C14—C23	111.8 (3)	C26—C35—H35B	109.5
C13—C14—C23	110.8 (3)	H35A—C35—H35B	109.5
C24—C14—C23	109.9 (3)	C26—C35—H35C	109.5
C16—C15—C20	119.8 (4)	H35A—C35—H35C	109.5
C16—C15—C14	131.8 (4)	H35B—C35—H35C	109.5
C20—C15—C14	108.3 (3)	C26—C36—H36A	109.5
C15—C16—C17	118.9 (4)	C26—C36—H36B	109.5
C15—C16—H16	120.5	H36A—C36—H36B	109.5
C17—C16—H16	120.5	C26—C36—H36C	109.5
C18—C17—C16	120.7 (4)	H36A—C36—H36C	109.5
C18—C17—H17	119.6	H36B—C36—H36C	109.5
C16—C17—H17	119.6

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the benzene C27–C32 and C3–C8 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱⁱ	0.95	2.40	3.353 (5)	177
C7—H7···O1ⁱ	0.95	2.34	2.965 (4)	123
C19—H19···O2ⁱⁱ	0.95	2.27	2.860 (5)	120
C31—H31···O3ⁱⁱⁱ	0.95	2.25	2.861 (5)	121
C9—H9···Cg1^iv	0.95	2.85	3.794 (5)	170
C33—H33···Cg2ⁱⁱ	0.95	2.76	3.630 (4)	153

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Pd(C₁₂H₁₂NO)₂]
M_r	478.85
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.453 (2), 12.669 (3), 13.056 (3)
α, β, γ (°)	87.750 (3), 73.271 (3), 70.565 (3)
V (Å³)	1558.5 (6)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.18 × 0.09 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.853, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	13381, 6083, 4905
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.095, 1.03
No. of reflections	6083
No. of parameters	403
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.35, −0.75

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the benzene C27–C32 and C3–C8 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.95	2.40	3.353 (5)	177
C7—H7···O1ⁱⁱ	0.95	2.34	2.965 (4)	123
C19—H19···O2ⁱ	0.95	2.27	2.860 (5)	120
C31—H31···O3ⁱⁱⁱ	0.95	2.25	2.861 (5)	121
C9—H9···Cg1^iv	0.95	2.85	3.794 (5)	170
C33—H33···Cg2ⁱ	0.95	2.76	3.630 (4)	153

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z; (iii) −x+1, −y+2, −z+1; (iv) x, y−1, z.

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP004/2010B).

References

Barbour, L. J. (2001). J. Supramol. Chem, 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khaledi, H., Mohd Ali, H. & Olmstead, M. M. (2011). Eur. J. Inorg. Chem. pp. 2394–2404. CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m929

doi:10.1107/S1600536811022069

Open

access