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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Nov 25;67(Pt 12):m1820. doi: 10.1107/S1600536811049348

trans-Bromido(pyrimidinyl-κC 5)bis­(triphenyl­phosphane-κP)palladium(II)

Hsiao-Fen Wang a, Weng-Feng Zeng b, Gene-Hsiang Lee c,*, Kuang-Hway Yih d,*
PMCID: PMC3238722  PMID: 22199599

Abstract

In the title complex, [PdBr(C4H3N2)(C18H15P)2], the geometry around the Pd atom is distorted square-planar with the Pd atom displaced by 0.0334 (14) Å from the BrP2C plane. The two Ph3P ligands are in trans positions, defining a P—Pd—P angle of 171.78 (5)°, while the pyrimidinyl and bromide ligands are trans to each other [C—Pd—Br = 174.63 (14)°].

Related literature

For reactions in organic synthesis that form C—C bonds, see: Steffen et al. (2005 ▶); Beeby et al. (2004 ▶); Chin et al. (1988 ▶); Dobrzynski & Angelici (1975 ▶). For Pd—C(carbene) bond lengths, see: Cardin et al. (1972 ▶) and for Pd—Br bond lengths, see: Yih & Lee (2008 ▶); Yih et al. (2009 ▶). For related structures of pyrimidin­yl–metal complexes, see: Hong et al. (2002 ▶).graphic file with name e-67-m1820-scheme1.jpg

Experimental

Crystal data

  • [PdBr(C4H3N2)(C18H15P)2]

  • M r = 789.93

  • Monoclinic, Inline graphic

  • a = 15.0953 (10) Å

  • b = 12.0379 (8) Å

  • c = 19.8066 (13) Å

  • β = 109.7481 (13)°

  • V = 3387.5 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.85 mm−1

  • T = 150 K

  • 0.35 × 0.20 × 0.12 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.563, T max = 0.808

  • 19582 measured reflections

  • 7764 independent reflections

  • 5553 reflections with I > 2σ(I)

  • R int = 0.079

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052

  • wR(F 2) = 0.132

  • S = 1.01

  • 7764 reflections

  • 415 parameters

  • H-atom parameters constrained

  • Δρmax = 0.87 e Å−3

  • Δρmin = −0.98 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049348/bg2434sup1.cif

e-67-m1820-sup1.cif (23.7KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049348/bg2434Isup2.hkl

e-67-m1820-Isup2.hkl (379.9KB, hkl)

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

Acknowledgments

We thank the National Science Council of the Republic of China for financial support (NSC100–2113-M-241–001-MY3).

supplementary crystallographic information

Comment

Palladium-complexes catalyzed formation of C—C bonds are some of the most important reactions in organic synthesis (Dobrzynski & Angelici, 1975). Intramolecular reductive elimination of Pd—N binuclear complex [Pd(µ-C9H6N)(µ-dppm)]2(Cl)2 yielding the organic compound 2,2'-biquinoline has been reported (Chin et al., 1988). A pyridyl-bridged palladium complex was reported as an effective precatalyst for the Suzuki cross-coupling reactions of a variety of organoboronic acids and aryl bromides (Beeby, et al., 2004). Pyrimidinyl nickel complexes have been used as catalysts for C—C coupling reactions (Steffen et al., 2005). To our knowledge, no 3,5-pyrimidinyl palladium crystal structure has been described so far.

To synthesize the pyrimidinyl metal compound, [Pd(PPh3)4] was used to react with 5-bromopyrimidine in dichloromethane at room temperature. As a result, a two triphenylphosphine displaced complex [Pd(Br)(C4H3N2)(PPh3)2] was isolated with 97% yield. The X-ray crystal structure analysis has been carried out to provide structural information.

The molecular structure of the title compound is shown in Fig. 1. The palladium atom has a distorted square planar environment, being displaced by 0.0396Å from the least-squares plane and with all angles about the Pd center within ± 2.6° of 90°. The Pd—C1 bond distance, 2.000 (5) Å, is longer than other PdII-carbon(carbonyl) distances, and similar to Pd—C(carbene) distances (Cardin et al., 1972). Two PPh3 ligands are in trans position: P1—Pd—P2, 171.78 (5)°, while the pyrimidinyl ligand and bromide are trans to each other: C1—Pd—Br, 174.63 (14)°. The phosphorus atoms approach tetrahedral geometry as expected. The largest angular deviation from ideal tetrahedral geometry is 119.31 (16)° for C5—P1—Pd. The mean Pd—N distance (> 4.25Å) indicates no bonding interaction between the nitrogen atom and the palladium metal atom. Within the pyrimidinyl ligand itself, the geometry is consistent with a significant partial double bond character in the C—C and C—N bonds. The C—N bond distances (1.315 (7) ~1.351 (6) Å) are typical for a C—N bond having partial double bond character and are certainly much shorter than the normal C—N (1.47 Å) single bond. The Pd—C1 (2.000 (5) Å), Pd—P (2.3175 (13), 2.3325 (13) Å) and Pd—Br (2.4907 (6) Å) lengths are in agreement with reported values (Yih et al., 2008, 2009).

TThe 31P{1H} NMR spectra of (I) shows a singlet resonances at δ 24.2. In the 1H NMR spectra, the 2,6-H and 4-H protons of the pyrimidinyl group exhibit two singlet resonances at δ 7.75 and at δ 8.05. The 13C{1H} NMR spectra of (I) reveals two singlets at δ 151.9 and at δ 161.4 which are assigned to the 4-C and 2,6-C carbon atom of the pyrimidinyl group. There is a triplet resonance at δ 154.4 (2JP—C = 5.91 Hz), which is assigned to the 1-C of pyrimidinyl group. In the FAB mass spectra, base peak with the typical Pd isotope distribution is in agreement with the [M+] molecular mass of (I).

Experimental

The synthesis of the title compound (I) was carried out as follows. CH2Cl2 (20 ml) was added to a flask (100 ml) containing Pd(PPh3)4 (1.155 g, 1.0 mmol) and 5-Bromopyrimidine (0.191 g, 1.2 mmol) at ambient temperature. The mixture was stirred for about 1 day. The solvent was concentrated to 10 ml, and 20 ml of diethyl ether was added to the solution. The yellow solids were formed which were isolated by filtration (G4), washed with n-hexane (2 × 10 ml) and subsequently dried under vacuum yielding 0.774 g (97%) of [Pd(PPh3)2(C4H3N2)Br], (I). Spectroscopic data: 31P{1H} NMR: δ 24.2 (s, PPh3). 1H NMR: δ 7.27–7.70 (m, 30H, 2PPh3), 7.75 (s, 2H, 2,6-H of pyrimidinyl), 8.05 (s, 1H, 4-H of pyrimidinyl). 13C{1H} NMR: δ 128.3 (m, o-C of Ph), 130.2 (m, p-C of Ph), 134.5 (m, m-C of Ph), 151.9 (s, 4-C of pyrimidinyl), 154.4 (t, 1-C of pyrimidinyl, 2JP—C = 5.91 Hz), 161.4 (s, 2,6-C of pyrimidinyl). MS (FAB, NBA, m/z): 789 [M+], 709 [M+ - Br], 630 [M+ - Br - pyrimidinyl]. Anal. Calcd. for C40H33BrN2P2Pd: C, 60.82; H, 4.21; N, 3.55. Found: C, 60.94; H, 4.31; N, 3.18.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95Å and with Uiso(H) = 1.2 times Ueq(C).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I), with 50% probability displacement ellipsoids.

Crystal data

[PdBr(C4H3N2)(C18H15P)2] F(000) = 1592
Mr = 789.93 Dx = 1.549 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 1845 reflections
a = 15.0953 (10) Å θ = 2.7–21.4°
b = 12.0379 (8) Å µ = 1.85 mm−1
c = 19.8066 (13) Å T = 150 K
β = 109.7481 (13)° Block, colourless
V = 3387.5 (4) Å3 0.35 × 0.20 × 0.12 mm
Z = 4
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Data collection

Bruker SMART APEX CCD area-detector diffractometer 7764 independent reflections
Radiation source: fine-focus sealed tube 5553 reflections with I > 2σ(I)
graphite Rint = 0.079
ω scans θmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001) h = −19→19
Tmin = 0.563, Tmax = 0.808 k = −15→11
19582 measured reflections l = −25→25
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Refinement

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)] = 0.052 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132 H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0532P)2] where P = (Fo2 + 2Fc2)/3
7764 reflections (Δ/σ)max < 0.001
415 parameters Δρmax = 0.87 e Å−3
0 restraints Δρmin = −0.98 e Å−3
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Pd 0.22914 (2) 0.92402 (3) 0.419184 (18) 0.01789 (11)
Br 0.12499 (4) 0.89245 (4) 0.29305 (3) 0.03315 (16)
P1 0.20103 (9) 1.11231 (10) 0.39822 (6) 0.0196 (3)
P2 0.23800 (8) 0.73438 (10) 0.44478 (6) 0.0193 (3)
N1 0.3674 (4) 0.9979 (4) 0.6421 (2) 0.0379 (12)
N2 0.4851 (3) 0.9595 (4) 0.5908 (3) 0.0399 (12)
C1 0.3223 (3) 0.9531 (4) 0.5168 (2) 0.0203 (10)
C2 0.4173 (3) 0.9424 (4) 0.5278 (3) 0.0278 (12)
H2 0.4355 0.9215 0.4881 0.033*
C3 0.4553 (4) 0.9840 (5) 0.6442 (3) 0.0414 (15)
H3 0.5026 0.9928 0.6899 0.050*
C4 0.3027 (4) 0.9829 (4) 0.5762 (3) 0.0267 (11)
H4 0.2385 0.9941 0.5712 0.032*
C5 0.2605 (3) 1.2118 (4) 0.4690 (2) 0.0223 (10)
C6 0.3583 (3) 1.2133 (4) 0.4915 (3) 0.0260 (11)
H6 0.3907 1.1635 0.4708 0.031*
C7 0.4086 (4) 1.2873 (4) 0.5441 (3) 0.0307 (12)
H7 0.4754 1.2876 0.5596 0.037*
C8 0.3617 (4) 1.3609 (5) 0.5739 (3) 0.0326 (13)
H8 0.3965 1.4115 0.6100 0.039*
C9 0.2654 (4) 1.3611 (4) 0.5517 (3) 0.0316 (13)
H9 0.2334 1.4118 0.5722 0.038*
C10 0.2140 (4) 1.2861 (4) 0.4986 (3) 0.0277 (11)
H10 0.1472 1.2864 0.4830 0.033*
C11 0.0758 (3) 1.1278 (4) 0.3800 (2) 0.0203 (10)
C12 0.0392 (3) 1.1108 (4) 0.4351 (3) 0.0257 (11)
H12 0.0809 1.1015 0.4829 0.031*
C13 −0.0575 (4) 1.1071 (4) 0.4209 (3) 0.0306 (12)
H13 −0.0818 1.0973 0.4589 0.037*
C14 −0.1174 (4) 1.1178 (4) 0.3517 (3) 0.0307 (12)
H14 −0.1835 1.1135 0.3417 0.037*
C15 −0.0831 (4) 1.1347 (4) 0.2967 (3) 0.0316 (12)
H15 −0.1255 1.1432 0.2490 0.038*
C16 0.0137 (4) 1.1395 (4) 0.3100 (3) 0.0282 (12)
H16 0.0371 1.1507 0.2717 0.034*
C17 0.2291 (3) 1.1726 (4) 0.3237 (2) 0.0220 (10)
C18 0.1997 (4) 1.2801 (4) 0.3004 (3) 0.0343 (13)
H18 0.1589 1.3190 0.3196 0.041*
C19 0.2303 (5) 1.3305 (5) 0.2486 (3) 0.0438 (16)
H19 0.2102 1.4036 0.2326 0.053*
C20 0.2897 (4) 1.2739 (6) 0.2209 (3) 0.0441 (16)
H20 0.3108 1.3083 0.1859 0.053*
C21 0.3181 (4) 1.1688 (6) 0.2435 (3) 0.0430 (15)
H21 0.3588 1.1304 0.2240 0.052*
C22 0.2884 (4) 1.1175 (5) 0.2944 (3) 0.0310 (12)
H22 0.3087 1.0441 0.3095 0.037*
C23 0.3086 (3) 0.6555 (4) 0.4031 (3) 0.0200 (10)
C24 0.3176 (3) 0.6939 (4) 0.3389 (3) 0.0234 (11)
H24 0.2923 0.7641 0.3201 0.028*
C25 0.3631 (3) 0.6297 (4) 0.3030 (3) 0.0272 (11)
H25 0.3677 0.6554 0.2590 0.033*
C26 0.4019 (3) 0.5289 (4) 0.3304 (3) 0.0284 (12)
H26 0.4325 0.4850 0.3050 0.034*
C27 0.3962 (4) 0.4918 (4) 0.3948 (3) 0.0300 (12)
H27 0.4246 0.4233 0.4145 0.036*
C28 0.3497 (4) 0.5535 (4) 0.4304 (3) 0.0274 (11)
H28 0.3453 0.5267 0.4742 0.033*
C29 0.2855 (3) 0.6946 (4) 0.5396 (2) 0.0212 (10)
C30 0.2263 (4) 0.6664 (4) 0.5774 (3) 0.0276 (12)
H30 0.1603 0.6619 0.5532 0.033*
C31 0.2627 (4) 0.6449 (4) 0.6502 (3) 0.0345 (13)
H31 0.2216 0.6261 0.6757 0.041*
C32 0.3587 (5) 0.6506 (4) 0.6860 (3) 0.0387 (15)
H32 0.3836 0.6347 0.7358 0.046*
C33 0.4183 (4) 0.6795 (4) 0.6493 (3) 0.0361 (14)
H33 0.4841 0.6849 0.6741 0.043*
C34 0.3826 (4) 0.7007 (4) 0.5763 (3) 0.0271 (11)
H34 0.4241 0.7193 0.5511 0.032*
C35 0.1230 (3) 0.6683 (4) 0.4145 (2) 0.0210 (10)
C36 0.1117 (4) 0.5551 (4) 0.4014 (3) 0.0320 (12)
H36 0.1654 0.5104 0.4062 0.038*
C37 0.0238 (4) 0.5062 (5) 0.3814 (3) 0.0405 (14)
H37 0.0166 0.4287 0.3720 0.049*
C38 −0.0542 (4) 0.5725 (6) 0.3752 (3) 0.0434 (16)
H38 −0.1150 0.5399 0.3615 0.052*
C39 −0.0443 (4) 0.6833 (5) 0.3887 (3) 0.0382 (14)
H39 −0.0980 0.7273 0.3849 0.046*
C40 0.0440 (3) 0.7326 (5) 0.4079 (3) 0.0295 (12)
H40 0.0504 0.8103 0.4166 0.035*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Pd 0.02109 (19) 0.01465 (19) 0.01659 (18) 0.00208 (14) 0.00463 (14) 0.00003 (15)
Br 0.0432 (3) 0.0249 (3) 0.0245 (3) 0.0058 (2) 0.0025 (2) −0.0019 (2)
P1 0.0242 (6) 0.0159 (6) 0.0184 (6) 0.0005 (5) 0.0068 (5) −0.0003 (5)
P2 0.0209 (6) 0.0172 (6) 0.0190 (6) 0.0009 (5) 0.0057 (5) −0.0001 (5)
N1 0.051 (3) 0.038 (3) 0.023 (2) −0.005 (2) 0.010 (2) −0.006 (2)
N2 0.034 (3) 0.046 (3) 0.035 (3) −0.009 (2) 0.005 (2) 0.002 (2)
C1 0.026 (3) 0.012 (2) 0.021 (2) −0.0011 (19) 0.007 (2) 0.0037 (19)
C2 0.022 (3) 0.036 (3) 0.024 (3) 0.001 (2) 0.007 (2) −0.001 (2)
C3 0.043 (4) 0.046 (4) 0.026 (3) −0.015 (3) −0.001 (3) 0.000 (3)
C4 0.027 (3) 0.016 (3) 0.038 (3) −0.002 (2) 0.012 (2) 0.003 (2)
C5 0.034 (3) 0.016 (2) 0.017 (2) −0.001 (2) 0.007 (2) −0.001 (2)
C6 0.027 (3) 0.027 (3) 0.026 (3) 0.000 (2) 0.011 (2) 0.002 (2)
C7 0.031 (3) 0.029 (3) 0.028 (3) −0.009 (2) 0.005 (2) 0.003 (2)
C8 0.046 (3) 0.031 (3) 0.022 (3) −0.016 (3) 0.013 (3) −0.008 (2)
C9 0.052 (4) 0.019 (3) 0.030 (3) −0.005 (2) 0.022 (3) −0.008 (2)
C10 0.034 (3) 0.025 (3) 0.026 (3) −0.001 (2) 0.013 (2) −0.001 (2)
C11 0.024 (3) 0.013 (2) 0.023 (2) 0.0009 (19) 0.007 (2) −0.001 (2)
C12 0.028 (3) 0.022 (3) 0.025 (3) 0.000 (2) 0.006 (2) 0.003 (2)
C13 0.032 (3) 0.031 (3) 0.033 (3) −0.001 (2) 0.017 (2) −0.003 (2)
C14 0.025 (3) 0.027 (3) 0.040 (3) 0.003 (2) 0.010 (2) 0.006 (3)
C15 0.030 (3) 0.025 (3) 0.035 (3) 0.005 (2) 0.004 (2) 0.005 (2)
C16 0.032 (3) 0.029 (3) 0.024 (3) 0.004 (2) 0.011 (2) 0.003 (2)
C17 0.029 (3) 0.020 (3) 0.015 (2) −0.003 (2) 0.005 (2) 0.001 (2)
C18 0.049 (4) 0.024 (3) 0.029 (3) 0.001 (3) 0.012 (3) −0.001 (2)
C19 0.069 (4) 0.023 (3) 0.035 (3) −0.013 (3) 0.012 (3) 0.007 (3)
C20 0.049 (4) 0.058 (4) 0.026 (3) −0.026 (3) 0.013 (3) 0.003 (3)
C21 0.039 (3) 0.062 (5) 0.032 (3) 0.002 (3) 0.017 (3) 0.010 (3)
C22 0.027 (3) 0.038 (3) 0.025 (3) 0.000 (2) 0.006 (2) 0.004 (2)
C23 0.016 (2) 0.019 (2) 0.024 (2) −0.0029 (19) 0.005 (2) −0.004 (2)
C24 0.028 (3) 0.017 (2) 0.024 (2) 0.005 (2) 0.007 (2) 0.001 (2)
C25 0.032 (3) 0.026 (3) 0.026 (3) −0.002 (2) 0.012 (2) −0.001 (2)
C26 0.029 (3) 0.025 (3) 0.036 (3) 0.003 (2) 0.017 (2) −0.005 (2)
C27 0.038 (3) 0.019 (3) 0.034 (3) 0.008 (2) 0.014 (2) 0.008 (2)
C28 0.034 (3) 0.021 (3) 0.030 (3) 0.001 (2) 0.014 (2) 0.001 (2)
C29 0.027 (3) 0.013 (2) 0.022 (2) 0.0030 (19) 0.005 (2) −0.001 (2)
C30 0.042 (3) 0.018 (3) 0.026 (3) −0.001 (2) 0.015 (2) −0.002 (2)
C31 0.057 (4) 0.026 (3) 0.028 (3) −0.002 (3) 0.024 (3) −0.004 (2)
C32 0.068 (4) 0.022 (3) 0.021 (3) 0.013 (3) 0.009 (3) 0.003 (2)
C33 0.043 (3) 0.021 (3) 0.032 (3) 0.015 (2) −0.005 (3) 0.003 (2)
C34 0.030 (3) 0.021 (3) 0.027 (3) 0.007 (2) 0.005 (2) −0.003 (2)
C35 0.021 (2) 0.021 (3) 0.020 (2) −0.0008 (19) 0.007 (2) −0.001 (2)
C36 0.027 (3) 0.029 (3) 0.038 (3) 0.000 (2) 0.009 (2) −0.004 (3)
C37 0.038 (3) 0.036 (3) 0.046 (4) −0.014 (3) 0.012 (3) −0.010 (3)
C38 0.030 (3) 0.064 (5) 0.036 (3) −0.023 (3) 0.011 (3) −0.008 (3)
C39 0.024 (3) 0.053 (4) 0.037 (3) 0.004 (3) 0.009 (3) 0.002 (3)
C40 0.031 (3) 0.033 (3) 0.024 (3) 0.000 (2) 0.010 (2) −0.005 (2)
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Geometric parameters (Å, °)

Pd—C1 2.000 (5) C18—C19 1.397 (8)
Pd—P1 2.3175 (13) C18—H18 0.9500
Pd—P2 2.3325 (13) C19—C20 1.379 (9)
Pd—Br 2.4907 (6) C19—H19 0.9500
P1—C11 1.811 (5) C20—C21 1.362 (8)
P1—C17 1.818 (5) C20—H20 0.9500
P1—C5 1.832 (5) C21—C22 1.379 (7)
P2—C35 1.817 (5) C21—H21 0.9500
P2—C23 1.821 (5) C22—H22 0.9500
P2—C29 1.834 (5) C23—C28 1.399 (7)
N1—C3 1.324 (7) C23—C24 1.401 (7)
N1—C4 1.351 (6) C24—C25 1.379 (7)
N2—C3 1.315 (7) C24—H24 0.9500
N2—C2 1.335 (7) C25—C26 1.376 (7)
C1—C4 1.356 (7) C25—H25 0.9500
C1—C2 1.381 (6) C26—C27 1.382 (7)
C2—H2 0.9500 C26—H26 0.9500
C3—H3 0.9500 C27—C28 1.369 (7)
C4—H4 0.9500 C27—H27 0.9500
C5—C10 1.383 (7) C28—H28 0.9500
C5—C6 1.391 (7) C29—C30 1.388 (7)
C6—C7 1.385 (7) C29—C34 1.401 (7)
C6—H6 0.9500 C30—C31 1.382 (7)
C7—C8 1.386 (7) C30—H30 0.9500
C7—H7 0.9500 C31—C32 1.383 (8)
C8—C9 1.369 (7) C31—H31 0.9500
C8—H8 0.9500 C32—C33 1.379 (8)
C9—C10 1.404 (7) C32—H32 0.9500
C9—H9 0.9500 C33—C34 1.385 (7)
C10—H10 0.9500 C33—H33 0.9500
C11—C12 1.393 (7) C34—H34 0.9500
C11—C16 1.394 (7) C35—C36 1.386 (7)
C12—C13 1.392 (7) C35—C40 1.391 (7)
C12—H12 0.9500 C36—C37 1.382 (7)
C13—C14 1.369 (7) C36—H36 0.9500
C13—H13 0.9500 C37—C38 1.394 (8)
C14—C15 1.371 (7) C37—H37 0.9500
C14—H14 0.9500 C38—C39 1.358 (8)
C15—C16 1.395 (7) C38—H38 0.9500
C15—H15 0.9500 C39—C40 1.390 (7)
C16—H16 0.9500 C39—H39 0.9500
C17—C22 1.389 (7) C40—H40 0.9500
C17—C18 1.396 (7)
C1—Pd—P1 91.64 (13) C18—C17—P1 120.2 (4)
C1—Pd—P2 89.49 (13) C17—C18—C19 119.9 (5)
P1—Pd—P2 171.78 (5) C17—C18—H18 120.0
C1—Pd—Br 174.63 (14) C19—C18—H18 120.0
P1—Pd—Br 87.38 (3) C20—C19—C18 119.9 (5)
P2—Pd—Br 92.24 (3) C20—C19—H19 120.1
C11—P1—C17 108.2 (2) C18—C19—H19 120.1
C11—P1—C5 107.1 (2) C21—C20—C19 120.2 (5)
C17—P1—C5 99.9 (2) C21—C20—H20 119.9
C11—P1—Pd 104.60 (15) C19—C20—H20 119.9
C17—P1—Pd 117.19 (16) C20—C21—C22 120.8 (6)
C5—P1—Pd 119.31 (16) C20—C21—H21 119.6
C35—P2—C23 105.2 (2) C22—C21—H21 119.6
C35—P2—C29 102.9 (2) C21—C22—C17 120.4 (5)
C23—P2—C29 104.1 (2) C21—C22—H22 119.8
C35—P2—Pd 112.25 (16) C17—C22—H22 119.8
C23—P2—Pd 114.27 (16) C28—C23—C24 118.3 (4)
C29—P2—Pd 116.86 (15) C28—C23—P2 122.2 (4)
C3—N1—C4 113.8 (5) C24—C23—P2 119.4 (4)
C3—N2—C2 115.1 (5) C25—C24—C23 120.0 (5)
C4—C1—C2 114.0 (4) C25—C24—H24 120.0
C4—C1—Pd 126.6 (4) C23—C24—H24 120.0
C2—C1—Pd 119.3 (4) C26—C25—C24 120.7 (5)
N2—C2—C1 124.0 (5) C26—C25—H25 119.6
N2—C2—H2 118.0 C24—C25—H25 119.6
C1—C2—H2 118.0 C25—C26—C27 119.8 (5)
N2—C3—N1 127.9 (5) C25—C26—H26 120.1
N2—C3—H3 116.1 C27—C26—H26 120.1
N1—C3—H3 116.1 C28—C27—C26 120.2 (5)
N1—C4—C1 125.1 (5) C28—C27—H27 119.9
N1—C4—H4 117.5 C26—C27—H27 119.9
C1—C4—H4 117.5 C27—C28—C23 121.0 (5)
C10—C5—C6 119.4 (5) C27—C28—H28 119.5
C10—C5—P1 124.0 (4) C23—C28—H28 119.5
C6—C5—P1 116.5 (4) C30—C29—C34 119.0 (5)
C7—C6—C5 120.1 (5) C30—C29—P2 121.1 (4)
C7—C6—H6 119.9 C34—C29—P2 119.7 (4)
C5—C6—H6 119.9 C31—C30—C29 120.4 (5)
C6—C7—C8 120.2 (5) C31—C30—H30 119.8
C6—C7—H7 119.9 C29—C30—H30 119.8
C8—C7—H7 119.9 C30—C31—C32 120.2 (5)
C9—C8—C7 120.3 (5) C30—C31—H31 119.9
C9—C8—H8 119.9 C32—C31—H31 119.9
C7—C8—H8 119.9 C33—C32—C31 120.0 (5)
C8—C9—C10 119.9 (5) C33—C32—H32 120.0
C8—C9—H9 120.1 C31—C32—H32 120.0
C10—C9—H9 120.1 C32—C33—C34 120.2 (5)
C5—C10—C9 120.1 (5) C32—C33—H33 119.9
C5—C10—H10 119.9 C34—C33—H33 119.9
C9—C10—H10 119.9 C33—C34—C29 120.1 (5)
C12—C11—C16 118.9 (4) C33—C34—H34 120.0
C12—C11—P1 119.5 (4) C29—C34—H34 120.0
C16—C11—P1 120.9 (4) C36—C35—C40 118.8 (5)
C13—C12—C11 120.8 (5) C36—C35—P2 122.4 (4)
C13—C12—H12 119.6 C40—C35—P2 118.7 (4)
C11—C12—H12 119.6 C37—C36—C35 121.2 (5)
C14—C13—C12 119.5 (5) C37—C36—H36 119.4
C14—C13—H13 120.2 C35—C36—H36 119.4
C12—C13—H13 120.2 C36—C37—C38 118.8 (6)
C13—C14—C15 120.7 (5) C36—C37—H37 120.6
C13—C14—H14 119.7 C38—C37—H37 120.6
C15—C14—H14 119.7 C39—C38—C37 120.8 (5)
C14—C15—C16 120.6 (5) C39—C38—H38 119.6
C14—C15—H15 119.7 C37—C38—H38 119.6
C16—C15—H15 119.7 C38—C39—C40 120.3 (5)
C11—C16—C15 119.6 (5) C38—C39—H39 119.9
C11—C16—H16 120.2 C40—C39—H39 119.9
C15—C16—H16 120.2 C39—C40—C35 120.0 (5)
C22—C17—C18 118.8 (5) C39—C40—H40 120.0
C22—C17—P1 120.6 (4) C35—C40—H40 120.0
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2434).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049348/bg2434sup1.cif

e-67-m1820-sup1.cif (23.7KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049348/bg2434Isup2.hkl

e-67-m1820-Isup2.hkl (379.9KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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