Dibromidobis[2-(dicyclo-hexyl-phosphan-yl)-biphenyl-κP]palladium(II).

The title compound, [PdBr(2)(C(24)H(31)P)(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 inter-molecular π-π inter-actions between the benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.949 (6) Å] are present via crystallographic inversion centres, resulting in a one-dimensional supra-molecular 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 = 967.14

Triclinic,

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[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.180

S = 1.10

3811 reflections

241 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −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.

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

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

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

[PdBr2(C24H31P)2]	Z = 1
Mr = 967.14	F(000) = 496
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0609P)2 + 7.3363P] where P = (Fo2 + 2Fc2)/3
3811 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −1.42 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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	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)

	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)

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)