(Acetato-κ(2)O,O')[2'-(di-tert-butyl-phosphanyl)-1,1'-biphenyl-κ(2)P,C(2)]palladium(II).

The structure of the title compound, [Pd(C(2)H(3)O(2))(C(20)H(26)P)], 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 intra-molecular C-H⋯O inter-action 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 = 462.82

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.014

wR(F 2) = 0.034

S = 1.06

5179 reflections

243 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: not determined

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040068/tk5150sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812040068/tk5150Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040068/tk5150Isup3.hkl

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

[Pd(C2H3O2)(C20H26P)]	F(000) = 952
Mr = 462.82	Dx = 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

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

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(Fo2) + (0.0177P)2 + 0.2811P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.002
5179 reflections	Δρmax = 0.27 e Å−3
243 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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
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)

	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)

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)

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

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