[2,6-Bis(5-eth­oxy-1,3-oxazol-2-yl)-4-meth­oxy­phenyl-κ3N,C1,N′]bromidopalladium(II)

Nan, W.-H.; Tan, J.-P.; Luo, Q.-L.

doi:10.1107/S1600536812049197

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Pages m31-m32

https://doi.org/10.1107/S1600536812049197

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[2,6-Bis(5-ethoxy-1,3-oxazol-2-yl)-4-methoxyphenyl-κ³N,C¹,N′]bromidopalladium(II)

Wen-Hui Nan,^a Jian-Ping Tan ^a and Qun-Li Luo ^a ^*

^aKey Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: qlluo@swu.edu.cn

(Received 16 November 2012; accepted 30 November 2012; online 8 December 2012)

In the title compound, [PdBr(C₁₇H₁₇N₂O₅)], the Pd^II atom is coordinated by an N,C¹,N′-tridentate pincer ligand and a Br atom in a distorted square-planar geometry. In the crystal, molecules are connected by C—H⋯Br and C—H⋯O hydrogen bonds, and π–π interactions between the oxazole and benzene rings [centroid–centroid distance = 3.7344 (19) Å], resulting in a three-dimensional supramolecular structure.

Related literature

For background to pincer palladium complexes, see: van Koten & Gebbink (2011 ); Moreno et al. (2010 ); Selander & Szabó (2011 ). For palladium complexes with NCN pincer ligands, see: Hao et al. (2010 ); Young et al. (2011 ). For studies on the chemistry of bis(oxazole) pincer palladium complexes, see: Luo et al. (2007 , 2011 ); Xu et al. (2011 ). For structures of related bis(azole) pincer palladium complexes, see: Ghorai et al. (2012 ); Luo et al. (2012 ).

Experimental

Crystal data

[PdBr(C₁₇H₁₇N₂O₅)]
M_r = 515.64
Triclinic, $[P \overline 1]$
a = 9.0209 (3) Å
b = 9.6544 (3) Å
c = 10.9200 (3) Å
α = 87.093 (2)°
β = 86.974 (1)°
γ = 85.793 (2)°
V = 946.11 (5) Å³
Z = 2
Mo Kα radiation
μ = 3.12 mm⁻¹
T = 296 K
0.43 × 0.41 × 0.37 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.347, T_max = 0.391
15776 measured reflections
4311 independent reflections
3770 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.113
S = 1.08
4311 reflections
235 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −1.25 e Å⁻³

Table 1
Selected bond lengths (Å)

Pd1—C11	1.954 (3)
Pd1—N1	2.056 (3)
Pd1—N2	2.055 (3)
Pd1—Br1	2.4941 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯Br1ⁱ	0.97	2.80	3.526 (5)	132
C16—H16A⋯O2ⁱⁱ	0.96	2.44	3.391 (5)	170
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x-1, y, z+1.

Data collection: SMART (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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812049197/hy2606sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049197/hy2606Isup2.hkl

checkCIF report

Comment top

Cross-coupling reactions catalyzed by palladium complexes are among the most important tools for C—C bond construction. Considerable attention has recently been devoted to pincer-Pd complexes due to their catalytic abilities (Ghorai et al., 2012; van Koten & Gebbink, 2011; Moreno et al., 2010; Selander & Szabó, 2011). We are interested in the NCN type of pincer-Pd complexes (Luo et al., 2007, 2011, 2012; Xu et al., 2011) as a variety of nonphosphine pincer catalytic system, that contains two nitrogen atoms as donating sites in the coordination sphere (Hao et al., 2010; Young et al., 2011)

The title compound was conveniently synthesized from the reaction of Pd(dba)₂ (dba = dibenzylideneacetone) with 1-bromo-2,6-bis(5-ethoxyoxazol-2-yl)-4-methoxy benzene in dry benzene under reflux in an argon atmosphere. As a result, the title compound was isolated with 84% yield. Suitable single crystals were grown via vapor diffusion of hexane into a DMF solution of the soluble reaction product at room temperature for dozens of days.

The molecular structure is shown in Fig. 1 and selected bond lengths in Table 1. In the crystal, the molecules are linked by intermolecular C—H···Br and C—H···O hydrogen bonds (Table 2) and π–π interactions between the oxazole and benzene rings [centroid–centroid distance = 3.7344 (19) Å], resulting in a three-dimensional supramolecular structure.

Related literature top

For background to pincer palladium complexes, see: van Koten & Gebbink (2011); Moreno et al. (2010); Selander & Szabó (2011). For palladium complexes with NCN pincer ligands, see: Hao et al. (2010); Young et al. (2011). For studies on the chemistry of bis(oxazole) pincer palladium complexes, see: Luo et al. (2007, 2011); Xu et al. (2011). For structures of related bis(azole) pincer palladium complexes, see: Ghorai et al. (2012); Luo et al. (2012).

Experimental top

Under an argon atmosphere, a 25 ml Schlenk flask was charged with 1-bromo-2,6-bis(5-ethoxyoxazol-2-yl)-4-methoxybenzene (106 mg, 0.3 mmol), Pd(dba)₂ (173 mg, 0.3 mmol) and dry benzene (15 ml). The reaction mixture was heated and refluxed for 2 h, and then cooled to room temperature and stirred for further 2 h. The resultant mixture was directly transferred on to a diatomite column and eluted first with hexane to remove dibenzylideneacetone and then with chloroform. The collected target compound was crystallized from CHCl₃/MeOH as a slight yellow solid (yield: 84%). ¹H NMR (300 MHz, CDCl₃): δ 6.76 (s, 2H), 6.52 (s, 2H), 4.25 (q, 4H, ³J = 6.9 Hz), 3.83 (s, 3H), 1.49 (t, 6H, ³J = 7.0 Hz). ¹³C NMR (75 MHz, CDCl₃): δ159.3, 158.5, 157.6, 154.7, 129.9, 107.3, 100.3, 55.8, 14.4. LRMS (ESI): m/z(%) 951 (100) (2M⁺–Br).

Structure description top

For background to pincer palladium complexes, see: van Koten & Gebbink (2011); Moreno et al. (2010); Selander & Szabó (2011). For palladium complexes with NCN pincer ligands, see: Hao et al. (2010); Young et al. (2011). For studies on the chemistry of bis(oxazole) pincer palladium complexes, see: Luo et al. (2007, 2011); Xu et al. (2011). For structures of related bis(azole) pincer palladium complexes, see: Ghorai et al. (2012); Luo et al. (2012).

Computing details top

Data collection: SMART (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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

[2,6-Bis(5-ethoxy-1,3-oxazol-2-yl)-4-methoxyphenyl- κ³N,C¹,N']bromidopalladium(II) top

Crystal data top

[PdBr(C₁₇H₁₇N₂O₅)]	Z = 2
M_r = 515.64	F(000) = 508
Triclinic, P1	D_x = 1.810 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0209 (3) Å	Cell parameters from 15776 reflections
b = 9.6544 (3) Å	θ = 1.9–27.5°
c = 10.9200 (3) Å	µ = 3.12 mm⁻¹
α = 87.093 (2)°	T = 296 K
β = 86.974 (1)°	Block, yellow
γ = 85.793 (2)°	0.43 × 0.41 × 0.37 mm
V = 946.11 (5) Å³

Data collection top

Bruker APEX CCD diffractometer	4311 independent reflections
Radiation source: fine-focus sealed tube	3770 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 0.01 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
T_min = 0.347, T_max = 0.391	l = −14→13
15776 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.080P)²] where P = (F_o² + 2F_c²)/3
4311 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.72 e Å⁻³
6 restraints	Δρ_min = −1.25 e Å⁻³

Crystal data top

[PdBr(C₁₇H₁₇N₂O₅)]	γ = 85.793 (2)°
M_r = 515.64	V = 946.11 (5) Å³
Triclinic, P1	Z = 2
a = 9.0209 (3) Å	Mo Kα radiation
b = 9.6544 (3) Å	µ = 3.12 mm⁻¹
c = 10.9200 (3) Å	T = 296 K
α = 87.093 (2)°	0.43 × 0.41 × 0.37 mm
β = 86.974 (1)°

Data collection top

Bruker APEX CCD diffractometer	4311 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3770 reflections with I > 2σ(I)
T_min = 0.347, T_max = 0.391	R_int = 0.034
15776 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	6 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	Δρ_max = 0.72 e Å⁻³
4311 reflections	Δρ_min = −1.25 e Å⁻³
235 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	0.75135 (2)	0.11221 (2)	0.04359 (2)	0.03536 (11)
Br1	0.73062 (5)	0.33747 (4)	0.14750 (4)	0.06338 (15)
O1	1.1647 (3)	0.2444 (3)	−0.3330 (3)	0.0641 (8)
O2	1.0326 (3)	0.0693 (2)	−0.2594 (2)	0.0427 (5)
O3	0.7890 (3)	−0.4275 (2)	−0.2212 (3)	0.0579 (7)
O4	0.4921 (3)	−0.1921 (2)	0.1850 (2)	0.0442 (5)
O5	0.3381 (3)	−0.1541 (3)	0.3498 (2)	0.0668 (8)
N1	0.9050 (3)	0.1515 (3)	−0.0974 (2)	0.0396 (6)
N2	0.6019 (3)	0.0043 (3)	0.1522 (2)	0.0400 (6)
C1	1.3044 (8)	0.4175 (6)	−0.4370 (6)	0.106 (2)
H1A	1.3264	0.5134	−0.4395	0.158*
H1B	1.2634	0.3971	−0.5128	0.158*
H1C	1.3941	0.3595	−0.4253	0.158*
C2	1.1945 (6)	0.3901 (4)	−0.3332 (5)	0.0810 (14)
H2A	1.2346	0.4105	−0.2560	0.097*
H2B	1.1033	0.4483	−0.3439	0.097*
C3	1.0668 (4)	0.2043 (3)	−0.2459 (3)	0.0447 (7)
C4	0.9916 (4)	0.2562 (3)	−0.1487 (3)	0.0426 (7)
H4A	0.9957	0.3450	−0.1203	0.051*
C5	0.9345 (3)	0.0438 (3)	−0.1655 (3)	0.0372 (6)
C6	0.8596 (3)	−0.0824 (3)	−0.1380 (3)	0.0372 (6)
C7	0.8675 (4)	−0.2063 (3)	−0.1977 (3)	0.0414 (7)
H7A	0.9331	−0.2201	−0.2653	0.050*
C8	0.7764 (4)	−0.3086 (3)	−0.1552 (3)	0.0436 (7)
C9	0.6796 (4)	−0.2931 (3)	−0.0517 (3)	0.0412 (7)
H9A	0.6196	−0.3635	−0.0233	0.049*
C10	0.6764 (3)	−0.1684 (3)	0.0073 (3)	0.0376 (7)
C11	0.7643 (3)	−0.0646 (3)	−0.0372 (3)	0.0358 (6)
C12	0.5894 (3)	−0.1220 (3)	0.1135 (3)	0.0384 (6)
C13	0.5062 (4)	0.0193 (4)	0.2543 (3)	0.0442 (7)
H13A	0.4905	0.0973	0.3011	0.053*
C14	0.4399 (4)	−0.1014 (4)	0.2730 (3)	0.0464 (8)
C15	0.2843 (5)	−0.0696 (5)	0.4494 (4)	0.0643 (11)
H15A	0.2321	0.0153	0.4183	0.077*
H15B	0.3666	−0.0450	0.4957	0.077*
C16	0.1823 (6)	−0.1520 (5)	0.5285 (4)	0.0837 (16)
H16A	0.1440	−0.0984	0.5963	0.126*
H16B	0.2351	−0.2356	0.5588	0.126*
H16C	0.1013	−0.1755	0.4817	0.126*
C17	0.6779 (5)	−0.5245 (4)	−0.1992 (4)	0.0587 (10)
H17A	0.6999	−0.6018	−0.2508	0.088*
H17B	0.5824	−0.4801	−0.2174	0.088*
H17C	0.6766	−0.5571	−0.1147	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.03735 (16)	0.03482 (16)	0.03421 (16)	−0.00236 (10)	−0.00149 (10)	−0.00492 (10)
Br1	0.0765 (3)	0.0515 (2)	0.0634 (3)	−0.0026 (2)	−0.0009 (2)	−0.0195 (2)
O1	0.0782 (19)	0.0491 (15)	0.0652 (17)	−0.0235 (14)	0.0259 (15)	−0.0074 (13)
O2	0.0477 (12)	0.0354 (11)	0.0450 (12)	−0.0084 (9)	0.0083 (10)	−0.0061 (9)
O3	0.0664 (16)	0.0390 (13)	0.0692 (17)	−0.0145 (11)	0.0214 (13)	−0.0205 (12)
O4	0.0478 (12)	0.0430 (12)	0.0422 (12)	−0.0101 (10)	0.0083 (10)	−0.0052 (10)
O5	0.085 (2)	0.0609 (17)	0.0537 (16)	−0.0198 (15)	0.0327 (14)	−0.0159 (13)
N1	0.0395 (14)	0.0366 (14)	0.0430 (15)	−0.0045 (11)	−0.0020 (11)	−0.0040 (11)
N2	0.0401 (14)	0.0455 (15)	0.0341 (13)	−0.0022 (11)	0.0030 (11)	−0.0050 (11)
C1	0.137 (5)	0.074 (3)	0.105 (4)	−0.041 (3)	0.041 (4)	0.002 (3)
C2	0.099 (4)	0.046 (2)	0.097 (4)	−0.021 (2)	0.031 (3)	0.002 (2)
C3	0.0479 (17)	0.0368 (16)	0.0498 (19)	−0.0109 (13)	0.0022 (15)	0.0012 (14)
C4	0.0460 (17)	0.0358 (16)	0.0465 (18)	−0.0063 (13)	−0.0014 (14)	−0.0026 (13)
C5	0.0371 (15)	0.0365 (15)	0.0382 (16)	−0.0038 (12)	−0.0014 (12)	−0.0021 (12)
C6	0.0366 (15)	0.0359 (15)	0.0391 (16)	−0.0016 (12)	−0.0028 (13)	−0.0008 (12)
C7	0.0407 (16)	0.0411 (17)	0.0419 (17)	−0.0036 (13)	0.0063 (13)	−0.0057 (13)
C8	0.0475 (18)	0.0355 (16)	0.0480 (19)	−0.0047 (13)	0.0041 (15)	−0.0090 (14)
C9	0.0419 (16)	0.0346 (15)	0.0471 (18)	−0.0078 (13)	0.0031 (14)	−0.0017 (13)
C10	0.0364 (15)	0.0415 (16)	0.0346 (16)	−0.0018 (12)	0.0016 (12)	−0.0029 (13)
C11	0.0336 (14)	0.0361 (15)	0.0380 (16)	−0.0044 (11)	−0.0021 (12)	−0.0007 (12)
C12	0.0405 (16)	0.0390 (16)	0.0359 (16)	−0.0048 (12)	0.0022 (13)	−0.0042 (12)
C13	0.0464 (18)	0.053 (2)	0.0333 (16)	−0.0022 (15)	0.0019 (14)	−0.0073 (14)
C14	0.0500 (19)	0.0526 (19)	0.0363 (17)	−0.0082 (15)	0.0096 (14)	−0.0059 (14)
C15	0.075 (3)	0.076 (3)	0.044 (2)	−0.017 (2)	0.0166 (19)	−0.0172 (18)
C16	0.112 (4)	0.081 (3)	0.054 (3)	−0.005 (3)	0.040 (3)	−0.011 (2)
C17	0.067 (2)	0.047 (2)	0.064 (2)	−0.0161 (18)	0.003 (2)	−0.0165 (18)

Geometric parameters (Å, º) top

Pd1—C11	1.954 (3)	C3—C4	1.328 (5)
Pd1—N1	2.056 (3)	C4—H4A	0.9300
Pd1—N2	2.055 (3)	C5—C6	1.447 (4)
Pd1—Br1	2.4941 (4)	C6—C11	1.371 (5)
O1—C3	1.326 (4)	C6—C7	1.387 (4)
O1—C2	1.451 (5)	C7—C8	1.378 (4)
O2—C5	1.344 (4)	C7—H7A	0.9300
O2—C3	1.378 (4)	C8—C9	1.399 (5)
O3—C8	1.380 (4)	C9—C10	1.392 (5)
O3—C17	1.425 (4)	C9—H9A	0.9300
O4—C12	1.342 (4)	C10—C11	1.377 (4)
O4—C14	1.374 (4)	C10—C12	1.438 (4)
O5—C14	1.323 (4)	C13—C14	1.350 (5)
O5—C15	1.435 (5)	C13—H13A	0.9300
N1—C5	1.312 (4)	C15—C16	1.475 (6)
N1—C4	1.400 (4)	C15—H15A	0.9700
N2—C12	1.325 (4)	C15—H15B	0.9700
N2—C13	1.380 (4)	C16—H16A	0.9600
C1—C2	1.492 (7)	C16—H16B	0.9600
C1—H1A	0.9600	C16—H16C	0.9600
C1—H1B	0.9600	C17—H17A	0.9600
C1—H1C	0.9600	C17—H17B	0.9600
C2—H2A	0.9700	C17—H17C	0.9600
C2—H2B	0.9700

C11—Pd1—N2	79.26 (12)	C8—C7—H7A	120.6
C11—Pd1—N1	79.31 (11)	C6—C7—H7A	120.6
N2—Pd1—N1	158.57 (11)	C7—C8—O3	115.2 (3)
C11—Pd1—Br1	179.10 (9)	C7—C8—C9	122.1 (3)
N2—Pd1—Br1	100.00 (8)	O3—C8—C9	122.7 (3)
N1—Pd1—Br1	101.42 (7)	C10—C9—C8	117.5 (3)
C3—O1—C2	114.6 (3)	C10—C9—H9A	121.3
C5—O2—C3	104.3 (2)	C8—C9—H9A	121.3
C8—O3—C17	118.0 (3)	C11—C10—C9	120.4 (3)
C12—O4—C14	104.9 (2)	C11—C10—C12	109.2 (3)
C14—O5—C15	116.3 (3)	C9—C10—C12	130.4 (3)
C5—N1—C4	106.2 (3)	C6—C11—C10	121.2 (3)
C5—N1—Pd1	112.1 (2)	C6—C11—Pd1	119.3 (2)
C4—N1—Pd1	141.7 (2)	C10—C11—Pd1	119.5 (2)
C12—N2—C13	107.0 (3)	N2—C12—O4	111.8 (3)
C12—N2—Pd1	112.0 (2)	N2—C12—C10	120.0 (3)
C13—N2—Pd1	141.0 (2)	O4—C12—C10	128.2 (3)
C2—C1—H1A	109.5	C14—C13—N2	106.6 (3)
C2—C1—H1B	109.5	C14—C13—H13A	126.7
H1A—C1—H1B	109.5	N2—C13—H13A	126.7
C2—C1—H1C	109.5	O5—C14—C13	137.7 (3)
H1A—C1—H1C	109.5	O5—C14—O4	112.5 (3)
H1B—C1—H1C	109.5	C13—C14—O4	109.7 (3)
O1—C2—C1	107.5 (4)	O5—C15—C16	107.2 (4)
O1—C2—H2A	110.2	O5—C15—H15A	110.3
C1—C2—H2A	110.2	C16—C15—H15A	110.3
O1—C2—H2B	110.2	O5—C15—H15B	110.3
C1—C2—H2B	110.2	C16—C15—H15B	110.3
H2A—C2—H2B	108.5	H15A—C15—H15B	108.5
O1—C3—C4	138.5 (3)	C15—C16—H16A	109.5
O1—C3—O2	111.2 (3)	C15—C16—H16B	109.5
C4—C3—O2	110.2 (3)	H16A—C16—H16B	109.5
C3—C4—N1	106.7 (3)	C15—C16—H16C	109.5
C3—C4—H4A	126.6	H16A—C16—H16C	109.5
N1—C4—H4A	126.6	H16B—C16—H16C	109.5
N1—C5—O2	112.5 (3)	O3—C17—H17A	109.5
N1—C5—C6	120.1 (3)	O3—C17—H17B	109.5
O2—C5—C6	127.3 (3)	H17A—C17—H17B	109.5
C11—C6—C7	119.9 (3)	O3—C17—H17C	109.5
C11—C6—C5	109.2 (3)	H17A—C17—H17C	109.5
C7—C6—C5	130.9 (3)	H17B—C17—H17C	109.5
C8—C7—C6	118.9 (3)

C11—Pd1—N1—C5	−1.0 (2)	C17—O3—C8—C9	13.7 (5)
N2—Pd1—N1—C5	−1.9 (4)	C7—C8—C9—C10	0.8 (5)
Br1—Pd1—N1—C5	179.6 (2)	O3—C8—C9—C10	−179.9 (3)
C11—Pd1—N1—C4	178.5 (4)	C8—C9—C10—C11	1.1 (5)
N2—Pd1—N1—C4	177.5 (3)	C8—C9—C10—C12	179.5 (3)
Br1—Pd1—N1—C4	−1.0 (4)	C7—C6—C11—C10	0.7 (5)
C11—Pd1—N2—C12	−0.9 (2)	C5—C6—C11—C10	178.7 (3)
N1—Pd1—N2—C12	0.1 (4)	C7—C6—C11—Pd1	−178.6 (2)
Br1—Pd1—N2—C12	178.6 (2)	C5—C6—C11—Pd1	−0.6 (4)
C11—Pd1—N2—C13	179.9 (4)	C9—C10—C11—C6	−1.9 (5)
N1—Pd1—N2—C13	−179.2 (3)	C12—C10—C11—C6	179.4 (3)
Br1—Pd1—N2—C13	−0.6 (4)	C9—C10—C11—Pd1	177.5 (2)
C3—O1—C2—C1	−179.3 (4)	C12—C10—C11—Pd1	−1.3 (4)
C2—O1—C3—C4	−6.5 (7)	N2—Pd1—C11—C6	−179.4 (3)
C2—O1—C3—O2	173.7 (4)	N1—Pd1—C11—C6	0.9 (2)
C5—O2—C3—O1	179.6 (3)	N2—Pd1—C11—C10	1.2 (2)
C5—O2—C3—C4	−0.3 (4)	N1—Pd1—C11—C10	−178.5 (3)
O1—C3—C4—N1	179.9 (4)	C13—N2—C12—O4	−0.7 (4)
O2—C3—C4—N1	−0.2 (4)	Pd1—N2—C12—O4	179.8 (2)
C5—N1—C4—C3	0.6 (4)	C13—N2—C12—C10	180.0 (3)
Pd1—N1—C4—C3	−178.8 (3)	Pd1—N2—C12—C10	0.5 (4)
C4—N1—C5—O2	−0.9 (3)	C14—O4—C12—N2	0.8 (4)
Pd1—N1—C5—O2	178.8 (2)	C14—O4—C12—C10	−180.0 (3)
C4—N1—C5—C6	−178.7 (3)	C11—C10—C12—N2	0.5 (4)
Pd1—N1—C5—C6	1.0 (4)	C9—C10—C12—N2	−178.1 (3)
C3—O2—C5—N1	0.7 (4)	C11—C10—C12—O4	−178.8 (3)
C3—O2—C5—C6	178.3 (3)	C9—C10—C12—O4	2.7 (6)
N1—C5—C6—C11	−0.3 (4)	C12—N2—C13—C14	0.3 (4)
O2—C5—C6—C11	−177.7 (3)	Pd1—N2—C13—C14	179.6 (3)
N1—C5—C6—C7	177.4 (3)	C15—O5—C14—C13	−5.6 (7)
O2—C5—C6—C7	0.0 (6)	C15—O5—C14—O4	176.2 (3)
C11—C6—C7—C8	1.2 (5)	N2—C13—C14—O5	−178.1 (4)
C5—C6—C7—C8	−176.3 (3)	N2—C13—C14—O4	0.1 (4)
C6—C7—C8—O3	178.8 (3)	C12—O4—C14—O5	178.2 (3)
C6—C7—C8—C9	−2.0 (5)	C12—O4—C14—C13	−0.5 (4)
C17—O3—C8—C7	−167.0 (3)	C14—O5—C15—C16	−175.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Br1ⁱ	0.97	2.80	3.526 (5)	132
C16—H16A···O2ⁱⁱ	0.96	2.44	3.391 (5)	170

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

Experimental details

Crystal data
Chemical formula	[PdBr(C₁₇H₁₇N₂O₅)]
M_r	515.64
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.0209 (3), 9.6544 (3), 10.9200 (3)
α, β, γ (°)	87.093 (2), 86.974 (1), 85.793 (2)
V (Å³)	946.11 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.12
Crystal size (mm)	0.43 × 0.41 × 0.37

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.347, 0.391
No. of measured, independent and observed [I > 2σ(I)] reflections	15776, 4311, 3770
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.113, 1.08
No. of reflections	4311
No. of parameters	235
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −1.25

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Pd1—C11	1.954 (3)	Pd1—N2	2.055 (3)
Pd1—N1	2.056 (3)	Pd1—Br1	2.4941 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Br1ⁱ	0.97	2.80	3.526 (5)	132
C16—H16A···O2ⁱⁱ	0.96	2.44	3.391 (5)	170

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

Acknowledgements

The authors appreciate financial support from the National Natural Science Foundation of China (grant No. 20971105) and the Fundamental Research Funds for the Central Universities (grant No. XDJK2012B011).

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