(Acetato-κ2O,O′)[2′-(di-tert-butyl­phosphanyl)-1,1′-biphenyl-κ2P,C2]palladium(II)

Arderne, C.; Holzapfel, C.W.

doi:10.1107/S1600536812040068

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1308

https://doi.org/10.1107/S1600536812040068

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(Acetato-κ²O,O′)[2′-(di-tert-butylphosphanyl)-1,1′-biphenyl-κ²P,C²]palladium(II)

Charmaine Arderne ^a ^* and Cedric W. Holzapfel ^a

^aDepartment of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, Johannesburg 2006, South Africa
^*Correspondence e-mail: carderne@uj.ac.za

(Received 12 September 2012; accepted 21 September 2012; online 26 September 2012)

The structure of the title compound, [Pd(C₂H₃O₂)(C₂₀H₂₆P)], shows a distorted square-planar geometry for the Pd^II atom, with significant deviations being evident owing to the asymmetric coordination mode of the acetate ligand. A weak intramolecular C—H⋯O interaction is noted. The crystal studied was a racemic twin.

Related literature

For related structures and catalytic literature on palladium complexes, see: Ormondi et al. (2011 ); van Blerk & Holzapfel (2009 ); Zim & Buchwald (2005 ); Williams et al. (2008 ).

Experimental

Crystal data

[Pd(C₂H₃O₂)(C₂₀H₂₆P)]
M_r = 462.82
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.800 (3) Å
b = 14.2392 (4) Å
c = 14.7772 (5) Å
V = 2062.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 100 K
0.25 × 0.19 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (AXSCALE; Bruker, 2010 ) T_min = 0.790, T_max = 0.874
24048 measured reflections
5179 independent reflections
5077 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.014
wR(F²) = 0.034
S = 1.06
5179 reflections
243 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: not determined

Table 1
Selected geometric parameters (Å, °)

Pd1—P1	2.2285 (7)
Pd1—O1	2.2109 (12)
Pd1—O2	2.1657 (11)
Pd1—C18	1.9686 (15)

P1—Pd1—O1	113.61 (3)
P1—Pd1—O2	173.58 (3)
P1—Pd1—C18	86.37 (4)
O1—Pd1—O2	60.19 (4)
O1—Pd1—C18	159.59 (5)
O2—Pd1—C18	99.69 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O1	0.98	2.25	3.169 (2)	156

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812040068/tk5150sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536812040068/tk5150Isup2.mol

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040068/tk5150Isup3.hkl

checkCIF report

Comment top

Our continued studies of palladium catalysed reactions (Ormondi et al., 2011; Williams et al., 2008; van Blerk & Holzapfel, 2009) includes a comparison of the efficiency of a wide range of palladocycles compared against the title compound (I), acetato-(2'-di-t-butylphosphanyl-1,1'-biphenyl-2yl)palladium(II). Compound (I) is an efficient and stable catalyst introduced by Zim & Buchwald (2005). We now report the crystal structure of (I) as part of a structure–activity study.

There is significant deviation from the ideal square planar geometry around the Pd atom as a result of its coordination to the acetate moiety. This distorted geometry is evident from the deviations in bond angles from 90°. The data in Table 1 demonstrate the deviations in the coordination geometry. A weak intramolecular C—H···O interaction is noted (Fig. 2 and Table 2).

Related literature top

For related structures and catalytic literature on palladium complexes, see: Ormondi et al. (2011); van Blerk & Holzapfel (2009); Zim & Buchwald (2005); Williams et al. (2008).

Experimental top

A solution of 2-(biphenyl)-di-tert-butylphosphine (298 mg; 1 mmol) and palladium acetate (224 mg; 1 mmol) in 15 ml of chloroform was refluxed under argon for 3 h. The solvent was evaporated in vacuo to leave a colourless crystalline residue (464 mg; ca 100%). The solid was taken up in dichloromethane (3 ml) and the solution diluted with cyclohexane (10 ml). The solvent was allowed to slowly evaporate in a stream of nitrogen until the solution was reduced to 3 ml. This resulted in the formation of well formed yellow blocks of the title compound (I) (288 mg; m.p. 409–414 K).

Structure description top

For related structures and catalytic literature on palladium complexes, see: Ormondi et al. (2011); van Blerk & Holzapfel (2009); Zim & Buchwald (2005); Williams et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of (I) with anisotropic displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Diagram of (I) showing the weak C—H···O intramolecular interaction indicating the H···A distance of 2.25 Å.

(Acetato-κ²O,O')[2'-(di-tert-butylphosphanyl)-1,1'- biphenyl-κ²P,C²]palladium(II) top

Crystal data top

[Pd(C₂H₃O₂)(C₂₀H₂₆P)]	F(000) = 952
M_r = 462.82	D_x = 1.491 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9242 reflections
a = 9.800 (3) Å	θ = 2.5–28.4°
b = 14.2392 (4) Å	µ = 0.99 mm⁻¹
c = 14.7772 (5) Å	T = 100 K
V = 2062.1 (6) Å³	Block, yellow
Z = 4	0.25 × 0.19 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	5179 independent reflections
Radiation source: fine-focus sealed tube	5077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
φ andω scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: multi-scan (AXSCALE; Bruker, 2010)	h = −13→12
T_min = 0.790, T_max = 0.874	k = −19→17
24048 measured reflections	l = −19→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.014	H-atom parameters constrained
wR(F²) = 0.034	w = 1/[σ²(F_o²) + (0.0177P)² + 0.2811P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
5179 reflections	Δρ_max = 0.27 e Å⁻³
243 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Crystal data top

[Pd(C₂H₃O₂)(C₂₀H₂₆P)]	V = 2062.1 (6) Å³
M_r = 462.82	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.800 (3) Å	µ = 0.99 mm⁻¹
b = 14.2392 (4) Å	T = 100 K
c = 14.7772 (5) Å	0.25 × 0.19 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	5179 independent reflections
Absorption correction: multi-scan (AXSCALE; Bruker, 2010)	5077 reflections with I > 2σ(I)
T_min = 0.790, T_max = 0.874	R_int = 0.018
24048 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.014	0 restraints
wR(F²) = 0.034	H-atom parameters constrained
S = 1.06	Δρ_max = 0.27 e Å⁻³
5179 reflections	Δρ_min = −0.19 e Å⁻³
243 parameters	Absolute structure: nd

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
C1	0.01684 (16)	0.64306 (10)	0.01415 (9)	0.0200 (3)
C2	−0.03332 (19)	0.70910 (12)	−0.05813 (11)	0.0296 (4)
H2A	0.0353	0.7580	−0.0688	0.044*
H2B	−0.1189	0.7383	−0.0384	0.044*
H2C	−0.0490	0.6740	−0.1142	0.044*
C3	−0.12994 (14)	0.36953 (10)	0.17962 (10)	0.0179 (3)
C4	−0.12773 (16)	0.35830 (11)	0.07523 (10)	0.0234 (3)
H4A	−0.0721	0.3036	0.0590	0.035*
H4B	−0.0886	0.4148	0.0477	0.035*
H4C	−0.2211	0.3493	0.0530	0.035*
C5	−0.22808 (14)	0.45126 (10)	0.20099 (10)	0.0207 (3)
H5A	−0.1956	0.5085	0.1712	0.031*
H5B	−0.2314	0.4613	0.2666	0.031*
H5C	−0.3196	0.4358	0.1788	0.031*
C6	−0.18496 (16)	0.27675 (11)	0.21887 (11)	0.0238 (3)
H6A	−0.1824	0.2795	0.2851	0.036*
H6B	−0.1283	0.2245	0.1978	0.036*
H6C	−0.2792	0.2673	0.1987	0.036*
C7	0.16700 (15)	0.30436 (10)	0.21904 (10)	0.0190 (3)
C8	0.15467 (17)	0.24809 (11)	0.13080 (13)	0.0300 (4)
H8A	0.1589	0.2911	0.0791	0.045*
H8B	0.0675	0.2144	0.1301	0.045*
H8C	0.2298	0.2029	0.1269	0.045*
C9	0.13811 (18)	0.24130 (12)	0.30108 (13)	0.0299 (4)
H9A	0.0436	0.2190	0.2985	0.045*
H9B	0.1520	0.2772	0.3569	0.045*
H9C	0.2003	0.1874	0.3002	0.045*
C10	0.31527 (15)	0.33883 (11)	0.22510 (12)	0.0238 (3)
H10A	0.3281	0.3739	0.2815	0.036*
H10B	0.3352	0.3798	0.1735	0.036*
H10C	0.3771	0.2848	0.2241	0.036*
C11	0.03089 (14)	0.44692 (9)	0.33655 (8)	0.0154 (3)
C12	−0.07717 (15)	0.41959 (11)	0.39277 (10)	0.0209 (3)
H12	−0.1366	0.3708	0.3735	0.025*
C13	−0.09954 (16)	0.46231 (12)	0.47641 (9)	0.0246 (3)
H13	−0.1752	0.4443	0.5127	0.029*
C14	−0.01070 (15)	0.53113 (13)	0.50607 (9)	0.0243 (3)
H14	−0.0268	0.5620	0.5620	0.029*
C15	0.10184 (17)	0.55503 (10)	0.45413 (9)	0.0201 (3)
H15	0.1646	0.6003	0.4765	0.024*
C16	0.12513 (13)	0.51377 (9)	0.36921 (9)	0.0163 (3)
C17	0.24987 (13)	0.54179 (10)	0.31892 (9)	0.0157 (2)
C18	0.25148 (14)	0.55169 (9)	0.22435 (9)	0.0147 (3)
C19	0.37097 (15)	0.58258 (10)	0.18224 (10)	0.0190 (3)
H19	0.3711	0.5933	0.1188	0.023*
C20	0.48925 (15)	0.59791 (11)	0.23147 (11)	0.0221 (3)
H20	0.5700	0.6179	0.2016	0.026*
C21	0.48961 (15)	0.58397 (11)	0.32458 (11)	0.0237 (3)
H21	0.5710	0.5926	0.3585	0.028*
C22	0.36993 (14)	0.55730 (9)	0.36744 (10)	0.0204 (3)
H22	0.3696	0.5494	0.4313	0.024*
O1	−0.05113 (11)	0.56989 (7)	0.03223 (7)	0.0211 (2)
O2	0.12585 (11)	0.66066 (7)	0.05752 (7)	0.0209 (2)
P1	0.04521 (4)	0.40789 (2)	0.21866 (2)	0.01354 (7)
Pd1	0.097889 (10)	0.536270 (7)	0.139786 (6)	0.01311 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0253 (8)	0.0188 (7)	0.0158 (6)	0.0050 (6)	0.0024 (6)	0.0028 (5)
C2	0.0350 (9)	0.0291 (9)	0.0248 (8)	0.0055 (7)	−0.0017 (7)	0.0105 (7)
C3	0.0173 (7)	0.0148 (7)	0.0215 (7)	−0.0024 (5)	−0.0021 (5)	−0.0004 (5)
C4	0.0266 (9)	0.0214 (7)	0.0223 (7)	−0.0019 (6)	−0.0036 (6)	−0.0044 (6)
C5	0.0159 (6)	0.0219 (8)	0.0245 (7)	0.0010 (6)	−0.0035 (5)	−0.0011 (6)
C6	0.0204 (7)	0.0191 (7)	0.0318 (8)	−0.0050 (6)	0.0008 (6)	0.0012 (6)
C7	0.0188 (7)	0.0129 (7)	0.0253 (7)	0.0026 (5)	0.0034 (6)	0.0028 (5)
C8	0.0268 (8)	0.0208 (8)	0.0424 (10)	0.0046 (6)	0.0002 (8)	−0.0107 (7)
C9	0.0258 (8)	0.0221 (8)	0.0419 (9)	0.0061 (6)	0.0066 (7)	0.0153 (7)
C10	0.0191 (7)	0.0154 (7)	0.0367 (9)	0.0035 (6)	0.0024 (6)	0.0026 (6)
C11	0.0154 (6)	0.0157 (7)	0.0151 (6)	0.0031 (5)	−0.0001 (5)	0.0028 (5)
C12	0.0190 (8)	0.0245 (7)	0.0191 (6)	−0.0029 (6)	0.0006 (5)	0.0041 (5)
C13	0.0202 (6)	0.0363 (8)	0.0173 (6)	0.0004 (9)	0.0039 (6)	0.0052 (6)
C14	0.0253 (7)	0.0332 (8)	0.0144 (6)	0.0058 (7)	0.0015 (5)	0.0004 (7)
C15	0.0206 (6)	0.0227 (7)	0.0171 (6)	0.0017 (6)	−0.0037 (6)	−0.0005 (5)
C16	0.0164 (6)	0.0163 (6)	0.0162 (6)	0.0032 (5)	−0.0019 (5)	0.0043 (5)
C17	0.0168 (6)	0.0104 (6)	0.0199 (6)	0.0012 (5)	0.0009 (5)	0.0015 (5)
C18	0.0165 (6)	0.0093 (6)	0.0183 (6)	0.0014 (5)	−0.0005 (5)	0.0000 (5)
C19	0.0211 (8)	0.0124 (6)	0.0235 (7)	0.0004 (5)	0.0041 (6)	0.0006 (5)
C20	0.0152 (7)	0.0178 (7)	0.0331 (8)	−0.0019 (6)	0.0036 (6)	0.0009 (6)
C21	0.0160 (7)	0.0213 (8)	0.0338 (8)	−0.0006 (6)	−0.0039 (6)	−0.0008 (6)
C22	0.0211 (7)	0.0181 (7)	0.0220 (6)	0.0005 (5)	−0.0030 (6)	−0.0008 (5)
O1	0.0249 (5)	0.0200 (5)	0.0185 (5)	0.0001 (4)	−0.0028 (4)	0.0025 (4)
O2	0.0241 (6)	0.0174 (5)	0.0211 (5)	−0.0008 (4)	0.0010 (4)	0.0054 (4)
P1	0.01417 (16)	0.01141 (16)	0.01505 (15)	0.00016 (13)	0.00127 (13)	0.00109 (12)
Pd1	0.01529 (5)	0.01095 (4)	0.01310 (4)	0.00049 (4)	0.00091 (4)	0.00145 (4)

Geometric parameters (Å, º) top

C1—O1	1.2651 (18)	C10—H10B	0.9800
C1—O2	1.2707 (19)	C10—H10C	0.9800
C1—C2	1.506 (2)	C11—C12	1.401 (2)
C2—H2A	0.9800	C11—C16	1.4114 (19)
C2—H2B	0.9800	C11—P1	1.8339 (14)
C2—H2C	0.9800	C12—C13	1.395 (2)
C3—C6	1.540 (2)	C12—H12	0.9500
C3—C5	1.542 (2)	C13—C14	1.382 (2)
C3—C4	1.551 (2)	C13—H13	0.9500
C3—P1	1.8915 (16)	C14—C15	1.386 (2)
C4—H4A	0.9800	C14—H14	0.9500
C4—H4B	0.9800	C15—C16	1.4043 (19)
C4—H4C	0.9800	C15—H15	0.9500
C5—H5A	0.9800	C16—C17	1.4852 (19)
C5—H5B	0.9800	C17—C22	1.3954 (19)
C5—H5C	0.9800	C17—C18	1.4046 (18)
C6—H6A	0.9800	C18—C19	1.397 (2)
C6—H6B	0.9800	C19—C20	1.386 (2)
C6—H6C	0.9800	C19—H19	0.9500
C7—C9	1.535 (2)	C20—C21	1.390 (2)
C7—C8	1.535 (2)	C20—H20	0.9500
C7—C10	1.536 (2)	C21—C22	1.386 (2)
C7—P1	1.8968 (15)	C21—H21	0.9500
C8—H8A	0.9800	C22—H22	0.9500
C8—H8B	0.9800	Pd1—P1	2.2285 (7)
C8—H8C	0.9800	Pd1—O1	2.2109 (12)
C9—H9A	0.9800	Pd1—O2	2.1657 (11)
C9—H9B	0.9800	Pd1—C1	2.5278 (15)
C9—H9C	0.9800	Pd1—C18	1.9686 (15)
C10—H10A	0.9800

O1—C1—O2	119.91 (13)	C7—C10—H10C	109.5
O1—C1—C2	119.48 (14)	H10A—C10—H10C	109.5
O2—C1—C2	120.60 (14)	H10B—C10—H10C	109.5
O1—C1—Pd1	60.99 (8)	C12—C11—C16	118.63 (13)
O2—C1—Pd1	58.94 (7)	C12—C11—P1	122.48 (11)
C2—C1—Pd1	177.93 (11)	C16—C11—P1	118.63 (10)
C1—C2—H2A	109.5	C13—C12—C11	121.54 (14)
C1—C2—H2B	109.5	C13—C12—H12	119.2
H2A—C2—H2B	109.5	C11—C12—H12	119.2
C1—C2—H2C	109.5	C14—C13—C12	119.42 (14)
H2A—C2—H2C	109.5	C14—C13—H13	120.3
H2B—C2—H2C	109.5	C12—C13—H13	120.3
C6—C3—C5	110.60 (12)	C13—C14—C15	119.98 (14)
C6—C3—C4	106.92 (12)	C13—C14—H14	120.0
C5—C3—C4	106.87 (12)	C15—C14—H14	120.0
C6—C3—P1	116.78 (10)	C14—C15—C16	121.43 (14)
C5—C3—P1	106.59 (10)	C14—C15—H15	119.3
C4—C3—P1	108.69 (10)	C16—C15—H15	119.3
C3—C4—H4A	109.5	C15—C16—C11	118.78 (12)
C3—C4—H4B	109.5	C15—C16—C17	117.94 (12)
H4A—C4—H4B	109.5	C11—C16—C17	123.28 (12)
C3—C4—H4C	109.5	C22—C17—C18	119.07 (13)
H4A—C4—H4C	109.5	C22—C17—C16	118.65 (12)
H4B—C4—H4C	109.5	C18—C17—C16	122.27 (12)
C3—C5—H5A	109.5	C19—C18—C17	118.95 (13)
C3—C5—H5B	109.5	C19—C18—Pd1	113.16 (10)
H5A—C5—H5B	109.5	C17—C18—Pd1	127.72 (10)
C3—C5—H5C	109.5	C20—C19—C18	121.12 (14)
H5A—C5—H5C	109.5	C20—C19—H19	119.4
H5B—C5—H5C	109.5	C18—C19—H19	119.4
C3—C6—H6A	109.5	C19—C20—C21	119.95 (14)
C3—C6—H6B	109.5	C19—C20—H20	120.0
H6A—C6—H6B	109.5	C21—C20—H20	120.0
C3—C6—H6C	109.5	C22—C21—C20	119.28 (14)
H6A—C6—H6C	109.5	C22—C21—H21	120.4
H6B—C6—H6C	109.5	C20—C21—H21	120.4
C9—C7—C8	110.54 (13)	C21—C22—C17	121.48 (14)
C9—C7—C10	108.38 (13)	C21—C22—H22	119.3
C8—C7—C10	106.90 (13)	C17—C22—H22	119.3
C9—C7—P1	109.94 (10)	C1—O1—Pd1	88.98 (9)
C8—C7—P1	110.71 (11)	C1—O2—Pd1	90.88 (9)
C10—C7—P1	110.30 (10)	C11—P1—C3	107.92 (7)
C7—C8—H8A	109.5	C11—P1—C7	106.31 (6)
C7—C8—H8B	109.5	C3—P1—C7	110.33 (7)
H8A—C8—H8B	109.5	C11—P1—Pd1	105.42 (5)
C7—C8—H8C	109.5	C3—P1—Pd1	106.72 (5)
H8A—C8—H8C	109.5	C7—P1—Pd1	119.56 (5)
H8B—C8—H8C	109.5	P1—Pd1—O1	113.61 (3)
C7—C9—H9A	109.5	P1—Pd1—O2	173.58 (3)
C7—C9—H9B	109.5	P1—Pd1—C18	86.37 (4)
H9A—C9—H9B	109.5	O1—Pd1—O2	60.19 (4)
C7—C9—H9C	109.5	O1—Pd1—C18	159.59 (5)
H9A—C9—H9C	109.5	O2—Pd1—C18	99.69 (5)
H9B—C9—H9C	109.5	C18—Pd1—C1	129.74 (5)
C7—C10—H10A	109.5	O2—Pd1—C1	30.17 (5)
C7—C10—H10B	109.5	O1—Pd1—C1	30.03 (4)
H10A—C10—H10B	109.5	P1—Pd1—C1	143.59 (4)

C16—C11—C12—C13	5.3 (2)	C4—C3—P1—C7	−77.17 (11)
P1—C11—C12—C13	−168.67 (11)	C6—C3—P1—Pd1	175.16 (10)
C11—C12—C13—C14	−2.1 (2)	C5—C3—P1—Pd1	−60.68 (10)
C12—C13—C14—C15	−2.0 (2)	C4—C3—P1—Pd1	54.18 (10)
C13—C14—C15—C16	2.9 (2)	C9—C7—P1—C11	40.82 (13)
C14—C15—C16—C11	0.3 (2)	C8—C7—P1—C11	163.24 (11)
C14—C15—C16—C17	−178.63 (13)	C10—C7—P1—C11	−78.65 (11)
C12—C11—C16—C15	−4.31 (19)	C9—C7—P1—C3	−75.95 (12)
P1—C11—C16—C15	169.90 (10)	C8—C7—P1—C3	46.47 (12)
C12—C11—C16—C17	174.56 (12)	C10—C7—P1—C3	164.59 (10)
P1—C11—C16—C17	−11.24 (18)	C9—C7—P1—Pd1	159.80 (9)
C15—C16—C17—C22	37.76 (18)	C8—C7—P1—Pd1	−77.78 (11)
C11—C16—C17—C22	−141.12 (14)	C10—C7—P1—Pd1	40.34 (12)
C15—C16—C17—C18	−143.27 (14)	C19—C18—Pd1—O2	−41.41 (11)
C11—C16—C17—C18	37.9 (2)	C17—C18—Pd1—O2	133.73 (12)
C22—C17—C18—C19	−4.0 (2)	C19—C18—Pd1—O1	−50.65 (19)
C16—C17—C18—C19	177.00 (12)	C17—C18—Pd1—O1	124.49 (14)
C22—C17—C18—Pd1	−178.92 (10)	C19—C18—Pd1—P1	140.72 (10)
C16—C17—C18—Pd1	2.1 (2)	C17—C18—Pd1—P1	−44.15 (12)
C17—C18—C19—C20	4.0 (2)	C19—C18—Pd1—C1	−44.46 (13)
Pd1—C18—C19—C20	179.56 (11)	C17—C18—Pd1—C1	130.67 (12)
C18—C19—C20—C21	−1.0 (2)	C1—O2—Pd1—C18	−175.32 (9)
C19—C20—C21—C22	−1.8 (2)	C1—O2—Pd1—O1	0.98 (8)
C20—C21—C22—C17	1.7 (2)	C1—O1—Pd1—C18	9.53 (17)
C18—C17—C22—C21	1.3 (2)	C1—O1—Pd1—O2	−0.98 (8)
C16—C17—C22—C21	−179.71 (13)	C1—O1—Pd1—P1	177.14 (7)
O2—C1—O1—Pd1	1.67 (13)	C11—P1—Pd1—C18	54.30 (6)
C2—C1—O1—Pd1	−177.69 (13)	C3—P1—Pd1—C18	168.90 (6)
O1—C1—O2—Pd1	−1.71 (13)	C7—P1—Pd1—C18	−65.13 (7)
C2—C1—O2—Pd1	177.65 (13)	C11—P1—Pd1—O1	−121.40 (6)
C12—C11—P1—C3	20.76 (14)	C3—P1—Pd1—O1	−6.80 (6)
C16—C11—P1—C3	−153.20 (11)	C7—P1—Pd1—O1	119.17 (7)
C12—C11—P1—C7	−97.61 (13)	C11—P1—Pd1—C1	−118.98 (7)
C16—C11—P1—C7	88.43 (12)	C3—P1—Pd1—C1	−4.39 (8)
C12—C11—P1—Pd1	134.52 (11)	C7—P1—Pd1—C1	121.59 (8)
C16—C11—P1—Pd1	−39.45 (11)	O1—C1—Pd1—C18	−175.69 (8)
C6—C3—P1—C11	−71.95 (12)	O2—C1—Pd1—C18	6.00 (11)
C5—C3—P1—C11	52.21 (11)	O1—C1—Pd1—O2	178.31 (13)
C4—C3—P1—C11	167.07 (10)	O2—C1—Pd1—O1	−178.31 (13)
C6—C3—P1—C7	43.81 (13)	O1—C1—Pd1—P1	−4.42 (11)
C5—C3—P1—C7	167.97 (9)	O2—C1—Pd1—P1	177.27 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1	0.98	2.25	3.169 (2)	156

Experimental details

Crystal data
Chemical formula	[Pd(C₂H₃O₂)(C₂₀H₂₆P)]
M_r	462.82
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	9.800 (3), 14.2392 (4), 14.7772 (5)
V (Å³)	2062.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.25 × 0.19 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (AXSCALE; Bruker, 2010)
T_min, T_max	0.790, 0.874
No. of measured, independent and observed [I > 2σ(I)] reflections	24048, 5179, 5077
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.014, 0.034, 1.06
No. of reflections	5179
No. of parameters	243
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.19
Absolute structure	Nd

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Pd1—P1	2.2285 (7)	Pd1—O2	2.1657 (11)
Pd1—O1	2.2109 (12)	Pd1—C18	1.9686 (15)

P1—Pd1—O1	113.61 (3)	O1—Pd1—O2	60.19 (4)
P1—Pd1—O2	173.58 (3)	O1—Pd1—C18	159.59 (5)
P1—Pd1—C18	86.37 (4)	O2—Pd1—C18	99.69 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1	0.98	2.25	3.169 (2)	156

Acknowledgements

The authors acknowledge the University of Johannesburg for the use of their facilities and for funding this project.

References

Blerk, C. van & Holzapfel, C. W. (2009). Acta Cryst. E65, m1536. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2010). APEX2, AXSCALE and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ormondi, B., Shaw, M. L. & Holzapfel, C. W. (2011). J. Organomet. Chem. 696, 3091–3096. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. 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
Williams, D. B. G., Shaw, M. L., Green, M. J. & Holzapfel, C. W. (2008). Angew. Chem. Int. Ed. 47, 560–563. Web of Science CrossRef CAS Google Scholar
Zim, D. & Buchwald, S. L. (2005). Org. Lett. 5, 2413–2415. Web of Science CrossRef Google Scholar

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