Dibromidobis[2-(dicyclo­hexyl­phosphan­yl)­biphenyl-κP]palladium(II)

Xu, C.; Li, Y.-F.; Wang, Z.-Q.; Cen, F.-F.; Zhang, Y.-Q.

doi:10.1107/S1600536808030845

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1349

doi:10.1107/S1600536808030845

Open

access

Dibromidobis[2-(dicyclohexylphosphanyl)biphenyl-κP]palladium(II)

Chen Xu,^a ^* Ying-Fei Li,^b Zhi-Qiang Wang,^a Fei-Fei Cen ^b and Yu-Qing Zhang ^b

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China, and ^bChemical Engineering and Pharmaceutics School, Henan University of Science and Technology, Luoyang 471003, People's Republic of China
^*Correspondence e-mail: xubohan@163.com

(Received 21 September 2008; accepted 24 September 2008; online 30 September 2008)

The title compound, [PdBr₂(C₂₄H₃₁P)₂], has a distorted trans square-planar coordination of the Pd atom, which occupies an inversion centre. The most important bond distances include Pd—P of 2.380 (2) Å and Pd—Br of 2.515 (2) Å. Weak intermolecular π–π interactions between the benzene rings of adjacent molecules [centroid–centroid distance = 3.949 (6) Å] are present via crystallographic inversion centres, resulting in a one-dimensional supramolecular architecture.

Related literature

For related literature, see: Barder et al. (2005 ); Christmann et al. (2006 ); Stark & Whitmire (1997 ); Tomori et al. (2000 ); Tsuji (1995 ); Xu et al. (2007 ).

Experimental

Crystal data

[PdBr₂(C₂₄H₃₁P)₂]
M_r = 967.14
Triclinic, $[P \overline 1]$
a = 9.817 (8) Å
b = 9.827 (8) Å
c = 11.957 (10) Å
α = 91.582 (11)°
β = 108.822 (10)°
γ = 103.713 (10)°
V = 1053.9 (15) Å³
Z = 1
Mo Kα radiation
μ = 2.44 mm⁻¹
T = 291 (2) K
0.14 × 0.10 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.723, T_max = 0.803
7316 measured reflections
3811 independent reflections
2810 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.180
S = 1.10
3811 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −1.42 e Å⁻³

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2003 ) and SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030845/si2114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030845/si2114Isup2.hkl

checkCIF report

Comment top

Phosphine complexes of palladium have widely been used as catalysts for various reactions (Tsuji, 1995). These complexes are easily prepared from palladium(II) salts and an excess of phosphine ligands. Among them, monophosphinobiaryl complexes of palladium are one of the most important ones (Barder et al., 2005; Christmann et al., 2006; Xu et al., 2007).

The title complex has crystallographic inversion symmetry C_i (Fig.1). The Pd atom is in a square-planar environment, while the trans 2-(Dicyclohexylphosphanyl)biphenyl ligands are in an eclipsed conformation. The dihedral angles of the benzene rings are 60.8 (2)°. The Pd—P [2.380 (2) Å] and Pd—Br [2.515 (5) Å] bond lengths are longer than the related triphenylphosphine complex of palladium [2.336 (2)Å and 2.4169 (13) Å](Stark & Whitmire, 1997) possibly due to the steric bulk of the ligand. Weak intermolecular π···π interactions between the benzene rings C19 - C24 (Cg4) of inversion related adjacent molecules [centroid-centroid distance Cg4···Cg4ⁱⁱ is 3.949 (6) Å, the perpendicular distance Cg4 on ring Cg4ⁱⁱ is 3.582 Å, and the slippage is 1.663 Å, symmetry code ii = 1 - x, 1 - y, 1 - z] were calculated for the structure of the title complex with the programme PLATON (Spek, 2003), resulting in a one-dimensional supramolecular architecture.

Related literature top

For related literature, see: Barder et al. (2005); Christmann et al. (2006); Stark & Whitmire (1997); Tomori et al. (2000); Tsuji (1995); Xu et al. (2007).

Experimental top

2-(Dicyclohexylphosphanyl)biphenyl was prepared as described in the literature (Tomori et al., 2000). A solution of PdBr₂(PhCN)₂ (1 mmol) and 2-(Dicyclohexylphosphanyl)biphenyl (2 mmol) in dry benzene (5 ml) was stirred for 1 day, removal of solvent resulted in a yellow powder that was recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired product as yellow crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2003) and SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids of the non-hydrogen atoms drawn at the 30% probability level. Inversion related atoms are labelled with an A.(Symmetry code: 2 - x, 1 - y, 1 - z).
	Fig. 2. Partial view of the crystal packing showing the formation of the chain motif of molecules formed by the intermolecular π···π interactions, extending along the a axis.

Dibromidobis[2-(dicyclohexylphosphanyl)biphenyl-κP]palladium(II) top

Crystal data top

[PdBr₂(C₂₄H₃₁P)₂]	Z = 1
M_r = 967.14	F(000) = 496
Triclinic, P1	D_x = 1.524 Mg m⁻³
a = 9.817 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.827 (8) Å	Cell parameters from 1503 reflections
c = 11.957 (10) Å	θ = 2.4–21.7°
α = 91.582 (11)°	µ = 2.45 mm⁻¹
β = 108.822 (10)°	T = 291 K
γ = 103.713 (10)°	Block, yellow
V = 1053.9 (15) Å³	0.14 × 0.10 × 0.09 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3811 independent reflections
Radiation source: fine-focus sealed tube	2810 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.723, T_max = 0.803	k = −11→11
7316 measured reflections	l = −14→14

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0609P)² + 7.3363P] where P = (F_o² + 2F_c²)/3
3811 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −1.42 e Å⁻³

Crystal data top

[PdBr₂(C₂₄H₃₁P)₂]	γ = 103.713 (10)°
M_r = 967.14	V = 1053.9 (15) Å³
Triclinic, P1	Z = 1
a = 9.817 (8) Å	Mo Kα radiation
b = 9.827 (8) Å	µ = 2.45 mm⁻¹
c = 11.957 (10) Å	T = 291 K
α = 91.582 (11)°	0.14 × 0.10 × 0.09 mm
β = 108.822 (10)°

Data collection top

Bruker SMART APEX CCD diffractometer	3811 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2810 reflections with I > 2σ(I)
T_min = 0.723, T_max = 0.803	R_int = 0.039
7316 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.10	Δρ_max = 0.71 e Å⁻³
3811 reflections	Δρ_min = −1.42 e Å⁻³
241 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	1.0000	0.5000	0.5000	0.0252 (2)
Br1	0.96825 (13)	0.71510 (13)	0.59715 (10)	0.0612 (4)
P1	0.8353 (2)	0.5540 (2)	0.32229 (17)	0.0267 (5)
C1	0.7959 (9)	0.4354 (9)	0.1852 (7)	0.0306 (18)
H1	0.7703	0.3392	0.2060	0.037*
C2	0.6642 (9)	0.4454 (10)	0.0766 (7)	0.038 (2)
H2A	0.5763	0.4378	0.0990	0.045*
H2B	0.6870	0.5358	0.0468	0.045*
C3	0.6343 (10)	0.3264 (10)	−0.0199 (8)	0.044 (2)
H3A	0.6021	0.2366	0.0078	0.053*
H3B	0.5546	0.3355	−0.0903	0.053*
C4	0.7702 (10)	0.3287 (10)	−0.0518 (8)	0.045 (2)
H4A	0.7945	0.4131	−0.0893	0.054*
H4B	0.7488	0.2479	−0.1090	0.054*
C5	0.9032 (10)	0.3258 (9)	0.0551 (8)	0.038 (2)
H5A	0.9903	0.3344	0.0315	0.046*
H5B	0.8843	0.2369	0.0879	0.046*
C6	0.9318 (9)	0.4476 (9)	0.1490 (7)	0.0362 (19)
H6A	1.0167	0.4456	0.2180	0.043*
H6B	0.9546	0.5366	0.1171	0.043*
C7	0.9148 (9)	0.7385 (9)	0.2981 (7)	0.0330 (18)
H7	0.9069	0.7981	0.3616	0.040*
C8	0.8334 (10)	0.7900 (9)	0.1839 (8)	0.044 (2)
H8A	0.8407	0.7375	0.1171	0.052*
H8B	0.7288	0.7724	0.1751	0.052*
C9	0.8963 (11)	0.9454 (10)	0.1819 (10)	0.056 (3)
H9A	0.8471	0.9723	0.1048	0.067*
H9B	0.8761	0.9987	0.2415	0.067*
C10	1.0617 (11)	0.9819 (11)	0.2059 (10)	0.057 (3)
H10A	1.0808	0.9410	0.1396	0.068*
H10B	1.0993	1.0835	0.2124	0.068*
C11	1.1426 (10)	0.9292 (10)	0.3177 (10)	0.054 (3)
H11A	1.1345	0.9794	0.3853	0.064*
H11B	1.2474	0.9482	0.3268	0.064*
C12	1.0801 (9)	0.7721 (9)	0.3166 (8)	0.039 (2)
H12A	1.1322	0.7419	0.3914	0.047*
H12B	1.0957	0.7210	0.2531	0.047*
C13	0.6373 (9)	0.2210 (10)	0.3590 (8)	0.043 (2)
H13	0.7063	0.2713	0.4296	0.052*
C14	0.6340 (11)	0.0838 (10)	0.3309 (9)	0.048 (2)
H14	0.7007	0.0422	0.3832	0.058*
C15	0.5362 (12)	0.0082 (11)	0.2291 (10)	0.055 (3)
H15	0.5373	−0.0841	0.2107	0.066*
C16	0.4362 (12)	0.0670 (11)	0.1533 (9)	0.056 (3)
H16	0.3689	0.0148	0.0829	0.067*
C17	0.4337 (10)	0.2035 (10)	0.1801 (8)	0.047 (2)
H17	0.3618	0.2412	0.1292	0.056*
C18	0.5374 (9)	0.2858 (9)	0.2823 (7)	0.0338 (19)
C19	0.5333 (9)	0.4319 (9)	0.3139 (7)	0.0324 (18)
C20	0.4018 (9)	0.4472 (10)	0.3274 (8)	0.043 (2)
H20	0.3219	0.3678	0.3114	0.051*
C21	0.3852 (10)	0.5738 (11)	0.3630 (8)	0.047 (2)
H21	0.2967	0.5795	0.3733	0.056*
C22	0.4983 (11)	0.6902 (11)	0.3831 (8)	0.046 (2)
H22	0.4871	0.7770	0.4056	0.056*
C23	0.6325 (10)	0.6814 (10)	0.3703 (8)	0.040 (2)
H23	0.7104	0.7626	0.3862	0.048*
C24	0.6521 (9)	0.5536 (9)	0.3340 (7)	0.0306 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0260 (5)	0.0262 (5)	0.0248 (5)	0.0099 (4)	0.0083 (3)	0.0043 (3)
Br1	0.0626 (7)	0.0682 (8)	0.0511 (7)	0.0210 (6)	0.0141 (5)	0.0072 (5)
P1	0.0255 (10)	0.0281 (11)	0.0275 (10)	0.0093 (8)	0.0084 (8)	0.0049 (8)
C1	0.032 (4)	0.035 (5)	0.031 (4)	0.014 (4)	0.014 (3)	0.007 (3)
C2	0.032 (4)	0.046 (5)	0.036 (5)	0.015 (4)	0.007 (4)	0.004 (4)
C3	0.043 (5)	0.054 (6)	0.029 (5)	0.009 (4)	0.007 (4)	0.000 (4)
C4	0.051 (6)	0.045 (6)	0.036 (5)	−0.001 (4)	0.021 (4)	−0.005 (4)
C5	0.047 (5)	0.036 (5)	0.043 (5)	0.015 (4)	0.028 (4)	0.004 (4)
C6	0.038 (5)	0.038 (5)	0.034 (4)	0.012 (4)	0.013 (4)	0.005 (4)
C7	0.032 (4)	0.035 (5)	0.036 (5)	0.014 (4)	0.012 (4)	0.007 (4)
C8	0.040 (5)	0.034 (5)	0.056 (6)	0.010 (4)	0.013 (4)	0.020 (4)
C9	0.047 (6)	0.039 (6)	0.077 (7)	0.012 (5)	0.013 (5)	0.024 (5)
C10	0.056 (6)	0.041 (6)	0.072 (7)	0.007 (5)	0.023 (6)	0.019 (5)
C11	0.033 (5)	0.050 (6)	0.073 (7)	0.002 (4)	0.019 (5)	0.013 (5)
C12	0.031 (4)	0.037 (5)	0.051 (5)	0.010 (4)	0.015 (4)	0.014 (4)
C13	0.031 (5)	0.059 (6)	0.039 (5)	0.016 (4)	0.008 (4)	0.010 (4)
C14	0.052 (6)	0.037 (6)	0.059 (6)	0.020 (5)	0.017 (5)	0.013 (5)
C15	0.059 (6)	0.032 (6)	0.068 (7)	0.005 (5)	0.021 (6)	−0.002 (5)
C16	0.055 (6)	0.046 (6)	0.052 (6)	−0.005 (5)	0.011 (5)	−0.004 (5)
C17	0.037 (5)	0.045 (6)	0.044 (5)	0.001 (4)	0.002 (4)	0.007 (4)
C18	0.030 (4)	0.031 (5)	0.039 (5)	0.003 (3)	0.015 (4)	0.003 (4)
C19	0.029 (4)	0.034 (5)	0.035 (4)	0.010 (3)	0.011 (3)	0.004 (4)
C20	0.027 (4)	0.048 (6)	0.052 (6)	0.010 (4)	0.012 (4)	0.007 (4)
C21	0.030 (5)	0.067 (7)	0.053 (6)	0.023 (5)	0.018 (4)	0.009 (5)
C22	0.055 (6)	0.051 (6)	0.051 (6)	0.034 (5)	0.026 (5)	0.012 (5)
C23	0.038 (5)	0.040 (5)	0.047 (5)	0.015 (4)	0.019 (4)	0.005 (4)
C24	0.033 (4)	0.034 (5)	0.029 (4)	0.014 (4)	0.012 (3)	0.006 (3)

Geometric parameters (Å, º) top

Pd1—P1ⁱ	2.380 (2)	C9—H9B	0.9700
Pd1—P1	2.380 (2)	C10—C11	1.495 (14)
Pd1—Br1ⁱ	2.515 (2)	C10—H10A	0.9700
Pd1—Br1	2.515 (2)	C10—H10B	0.9700
P1—C24	1.848 (8)	C11—C12	1.518 (13)
P1—C1	1.862 (8)	C11—H11A	0.9700
P1—C7	1.866 (8)	C11—H11B	0.9700
C1—C6	1.510 (11)	C12—H12A	0.9700
C1—C2	1.533 (11)	C12—H12B	0.9700
C1—H1	0.9800	C13—C14	1.371 (13)
C2—C3	1.527 (12)	C13—C18	1.398 (12)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C15	1.347 (14)
C3—C4	1.496 (12)	C14—H14	0.9300
C3—H3A	0.9700	C15—C16	1.358 (14)
C3—H3B	0.9700	C15—H15	0.9300
C4—C5	1.511 (12)	C16—C17	1.378 (14)
C4—H4A	0.9700	C16—H16	0.9300
C4—H4B	0.9700	C17—C18	1.391 (12)
C5—C6	1.527 (11)	C17—H17	0.9300
C5—H5A	0.9700	C18—C19	1.488 (12)
C5—H5B	0.9700	C19—C20	1.393 (11)
C6—H6A	0.9700	C19—C24	1.410 (11)
C6—H6B	0.9700	C20—C21	1.367 (13)
C7—C8	1.512 (11)	C20—H20	0.9300
C7—C12	1.518 (11)	C21—C22	1.345 (14)
C7—H7	0.9800	C21—H21	0.9300
C8—C9	1.509 (12)	C22—C23	1.396 (12)
C8—H8A	0.9700	C22—H22	0.9300
C8—H8B	0.9700	C23—C24	1.394 (12)
C9—C10	1.505 (14)	C23—H23	0.9300
C9—H9A	0.9700

P1ⁱ—Pd1—P1	180.0	C10—C9—C8	111.9 (8)
P1ⁱ—Pd1—Br1ⁱ	85.15 (7)	C10—C9—H9A	109.2
P1—Pd1—Br1ⁱ	94.85 (7)	C8—C9—H9A	109.2
P1ⁱ—Pd1—Br1	94.85 (7)	C10—C9—H9B	109.2
P1—Pd1—Br1	85.15 (7)	C8—C9—H9B	109.2
Br1ⁱ—Pd1—Br1	180.000 (2)	H9A—C9—H9B	107.9
C24—P1—C1	106.1 (4)	C11—C10—C9	111.8 (8)
C24—P1—C7	104.9 (4)	C11—C10—H10A	109.2
C1—P1—C7	108.6 (4)	C9—C10—H10A	109.2
C24—P1—Pd1	112.3 (3)	C11—C10—H10B	109.2
C1—P1—Pd1	115.8 (3)	C9—C10—H10B	109.2
C7—P1—Pd1	108.5 (3)	H10A—C10—H10B	107.9
C6—C1—C2	109.2 (7)	C10—C11—C12	111.6 (8)
C6—C1—P1	112.5 (6)	C10—C11—H11A	109.3
C2—C1—P1	116.7 (5)	C12—C11—H11A	109.3
C6—C1—H1	105.9	C10—C11—H11B	109.3
C2—C1—H1	105.9	C12—C11—H11B	109.3
P1—C1—H1	105.9	H11A—C11—H11B	108.0
C3—C2—C1	109.1 (7)	C11—C12—C7	110.5 (7)
C3—C2—H2A	109.9	C11—C12—H12A	109.6
C1—C2—H2A	109.9	C7—C12—H12A	109.6
C3—C2—H2B	109.9	C11—C12—H12B	109.6
C1—C2—H2B	109.9	C7—C12—H12B	109.6
H2A—C2—H2B	108.3	H12A—C12—H12B	108.1
C4—C3—C2	111.7 (7)	C14—C13—C18	120.4 (9)
C4—C3—H3A	109.3	C14—C13—H13	119.8
C2—C3—H3A	109.3	C18—C13—H13	119.8
C4—C3—H3B	109.3	C15—C14—C13	121.4 (9)
C2—C3—H3B	109.3	C15—C14—H14	119.3
H3A—C3—H3B	107.9	C13—C14—H14	119.3
C3—C4—C5	112.5 (7)	C14—C15—C16	119.8 (10)
C3—C4—H4A	109.1	C14—C15—H15	120.1
C5—C4—H4A	109.1	C16—C15—H15	120.1
C3—C4—H4B	109.1	C15—C16—C17	120.4 (10)
C5—C4—H4B	109.1	C15—C16—H16	119.8
H4A—C4—H4B	107.8	C17—C16—H16	119.8
C4—C5—C6	109.5 (7)	C16—C17—C18	120.9 (9)
C4—C5—H5A	109.8	C16—C17—H17	119.6
C6—C5—H5A	109.8	C18—C17—H17	119.6
C4—C5—H5B	109.8	C17—C18—C13	117.0 (8)
C6—C5—H5B	109.8	C17—C18—C19	121.4 (8)
H5A—C5—H5B	108.2	C13—C18—C19	121.4 (8)
C1—C6—C5	110.0 (7)	C20—C19—C24	118.2 (8)
C1—C6—H6A	109.7	C20—C19—C18	116.4 (7)
C5—C6—H6A	109.7	C24—C19—C18	125.4 (7)
C1—C6—H6B	109.7	C21—C20—C19	122.8 (9)
C5—C6—H6B	109.7	C21—C20—H20	118.6
H6A—C6—H6B	108.2	C19—C20—H20	118.6
C8—C7—C12	109.9 (7)	C22—C21—C20	119.2 (8)
C8—C7—P1	117.0 (6)	C22—C21—H21	120.4
C12—C7—P1	113.5 (5)	C20—C21—H21	120.4
C8—C7—H7	105.1	C21—C22—C23	120.5 (9)
C12—C7—H7	105.1	C21—C22—H22	119.8
P1—C7—H7	105.1	C23—C22—H22	119.8
C9—C8—C7	111.9 (8)	C24—C23—C22	121.3 (9)
C9—C8—H8A	109.2	C24—C23—H23	119.3
C7—C8—H8A	109.2	C22—C23—H23	119.3
C9—C8—H8B	109.2	C23—C24—C19	117.9 (7)
C7—C8—H8B	109.2	C23—C24—P1	117.6 (6)
H8A—C8—H8B	107.9	C19—C24—P1	124.5 (6)

P1ⁱ—Pd1—P1—C24	103 (35)	C9—C10—C11—C12	54.5 (12)
Br1ⁱ—Pd1—P1—C24	120.1 (3)	C10—C11—C12—C7	−57.0 (11)
Br1—Pd1—P1—C24	−59.9 (3)	C8—C7—C12—C11	57.1 (10)
P1ⁱ—Pd1—P1—C1	−20 (33)	P1—C7—C12—C11	−169.7 (7)
Br1ⁱ—Pd1—P1—C1	−2.1 (3)	C18—C13—C14—C15	0.5 (15)
Br1—Pd1—P1—C1	177.9 (3)	C13—C14—C15—C16	−1.5 (16)
P1ⁱ—Pd1—P1—C7	−142 (33)	C14—C15—C16—C17	−0.2 (16)
Br1ⁱ—Pd1—P1—C7	−124.4 (3)	C15—C16—C17—C18	2.9 (15)
Br1—Pd1—P1—C7	55.6 (3)	C16—C17—C18—C13	−3.7 (14)
C24—P1—C1—C6	168.1 (6)	C16—C17—C18—C19	−178.3 (9)
C7—P1—C1—C6	55.8 (6)	C14—C13—C18—C17	2.1 (13)
Pd1—P1—C1—C6	−66.5 (6)	C14—C13—C18—C19	176.6 (8)
C24—P1—C1—C2	40.7 (7)	C17—C18—C19—C20	57.9 (11)
C7—P1—C1—C2	−71.6 (7)	C13—C18—C19—C20	−116.4 (9)
Pd1—P1—C1—C2	166.1 (5)	C17—C18—C19—C24	−123.8 (9)
C6—C1—C2—C3	59.6 (9)	C13—C18—C19—C24	61.9 (12)
P1—C1—C2—C3	−171.5 (6)	C24—C19—C20—C21	−2.3 (13)
C1—C2—C3—C4	−55.9 (10)	C18—C19—C20—C21	176.1 (8)
C2—C3—C4—C5	54.7 (11)	C19—C20—C21—C22	1.9 (14)
C3—C4—C5—C6	−55.3 (10)	C20—C21—C22—C23	−1.4 (14)
C2—C1—C6—C5	−61.9 (9)	C21—C22—C23—C24	1.5 (14)
P1—C1—C6—C5	166.9 (6)	C22—C23—C24—C19	−1.8 (12)
C4—C5—C6—C1	58.9 (9)	C22—C23—C24—P1	−179.1 (7)
C24—P1—C7—C8	−64.7 (7)	C20—C19—C24—C23	2.2 (12)
C1—P1—C7—C8	48.4 (7)	C18—C19—C24—C23	−176.0 (8)
Pd1—P1—C7—C8	175.1 (6)	C20—C19—C24—P1	179.2 (6)
C24—P1—C7—C12	165.6 (6)	C18—C19—C24—P1	1.0 (12)
C1—P1—C7—C12	−81.3 (7)	C1—P1—C24—C23	−139.6 (6)
Pd1—P1—C7—C12	45.3 (7)	C7—P1—C24—C23	−24.7 (7)
C12—C7—C8—C9	−56.0 (10)	Pd1—P1—C24—C23	93.0 (6)
P1—C7—C8—C9	172.6 (7)	C1—P1—C24—C19	43.4 (8)
C7—C8—C9—C10	54.0 (12)	C7—P1—C24—C19	158.3 (7)
C8—C9—C10—C11	−52.8 (13)	Pd1—P1—C24—C19	−84.1 (7)

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[PdBr₂(C₂₄H₃₁P)₂]
M_r	967.14
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	9.817 (8), 9.827 (8), 11.957 (10)
α, β, γ (°)	91.582 (11), 108.822 (10), 103.713 (10)
V (Å³)	1053.9 (15)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.45
Crystal size (mm)	0.14 × 0.10 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.723, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	7316, 3811, 2810
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.180, 1.10
No. of reflections	3811
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −1.42

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Doctoral Foundation of Luoyang Normal University, People's Republic of China.

References

Barder, T. E., Walker, S. D., Martinelli, J. R. & Buchwald, S. L. (2005). J. Am. Chem. Soc. 127, 4685–4696. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Christmann, U., Pantazis, D. A., Benet-Buchholz, J., McGrady, J. E., Maseras, F. & Vilar, R. (2006). J. Am. Chem. Soc. 128, 6376–6390. Web of Science CSD CrossRef PubMed CAS 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stark, J. L. & Whitmire, K. H. (1997). Acta Cryst. C53, IUC9700007. CrossRef IUCr Journals Google Scholar
Tomori, H., Fox, J. M. & Buchwald, S. L. (2000). J. Org. Chem. 65, 5334–5341. Web of Science CrossRef PubMed CAS Google Scholar
Tsuji, J. (1995). Palladium Reagents and Catalysts. Chichester: Wiley. Google Scholar
Xu, C., Gong, J. F. & Wu, Y. J. (2007). Tetrahedron Lett. 48, 1619–1623. Web of Science CSD CrossRef CAS Google Scholar