[2,6-Bis(5-eth-oxy-1,3-oxazol-2-yl)-4-meth-oxy-phenyl-κ(3) N,C (1),N']bromidopalladium(II).

In the title compound, [PdBr(C17H17N2O5)], the Pd(II) atom is coordinated by an N,C(1),N'-tridentate pincer ligand and a Br atom in a distorted square-planar geometry. In the crystal, mol-ecules are connected by C-H⋯Br and C-H⋯O hydrogen bonds, and π-π inter-actions between the oxazole and benzene rings [centroid-centroid distance = 3.7344 (19) Å], resulting in a three-dimensional supra-molecular structure.

Related literature

For background to pincer palladium complexes, see: van Koten & Gebbink (2011 ▶); Moreno et al. (2010 ▶); Selander & Szabó (2011 ▶). For n class="Chemical">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 = 515.64

Triclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.113

S = 1.08

4311 reflections

235 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −1.25 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049197/hy2606sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049197/hy2606Isup2.hkl

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

[PdBr(C17H17N2O5)]	Z = 2
Mr = 515.64	F(000) = 508
Triclinic, P1	Dx = 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

Bruker APEX CCD diffractometer	4311 independent reflections
Radiation source: fine-focus sealed tube	3770 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 0.01 pixels mm-1	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.347, Tmax = 0.391	l = −14→13
15776 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) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.080P)2] where P = (Fo2 + 2Fc2)/3
4311 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.72 e Å−3
6 restraints	Δρmin = −1.25 e Å−3

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	0.75135 (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*

	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)

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)

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

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) ; (ii) .