metal-organic compounds
trans-Iodido(pyrazinyl-κC2)bis(triphenylphosphane-κP)palladium(II)
aCollege of Environmental Sciences and Engineering, Peking University, Beijing 100871, People's Republic of China, bDepartment of Hair Styling and Design, Hungkuang University, Shalu 433, Taichung, Taiwan, ROC, cInstrumentation Center, College of Science, National Taiwan University, Taipei 106, Taiwan, ROC, and dDepartment of Applied Cosmetology, Hungkuang University, Shalu 433, Taichung, Taiwan, ROC
*Correspondence e-mail: ygl615@yahoo.com.tw, ghlee@ntu.edu.tw
There are two independent molecules with similar configurations in the 4H3N2)I(C18H15P)2]. In each molecule, the geometry around the Pd atom is distorted square-planar, with the Pd atom displaced by 0.0549 (12) and 0.0734 (13) Å from the least-squares plane of the I—P—P—C atoms. The PPh3 ligands are in trans positions, with P—Pd—P angles of 173.12 (4) and 170.29 (4)°, while the pyrazinyl ligands and I atoms, also trans to each other, form C—Pd—I angles of 179.38 (12) and 178.44 (12)°. In the crystal, C—H⋯π interactions occur, resulting in a three-dimensional supramolecular architecture.
of the title complex, [Pd(CRelated 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—I bond lengths, see: Yih et al. (2009). For intramolecular π–π interactions, see: Bustos et al. (2006). For a Pd–pyrimidinyl complex, see: Wang et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2007); cell 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.
Supporting information
10.1107/S1600536812043589/bg2480sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043589/bg2480Isup2.hkl
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 2-iodiopyrazine (0.248 g, 1.2 mmol) at ambient temperature. The mixture was stirred for about 10 min. The solvent was concentrated to 10 ml, and 20 ml of diethyl ether was added to the solution. The pale-yellow solids were formed which were isolated by filtration (G4), washed with n-hexane (2 x 10 ml) and subsequently dried under vacuum yielding 0.82 g (98%) of [Pd(PPh3)2(C4H3N2)I], (I).
H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å and with Uiso(H) = 1.2 times Ueq(C).
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and the 50% probability displacement ellipsoids. Dashed lines represent the π-π interactions. | |
Fig. 2. The molecular structure of (I), showing the intermolecular C—H···π hydrogen bond interactions. |
[Pd(C4H3N2)I(C18H15P)2] | F(000) = 3328 |
Mr = 836.92 | Dx = 1.601 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4895 reflections |
a = 21.5786 (9) Å | θ = 2.2–25.3° |
b = 19.8596 (9) Å | µ = 1.55 mm−1 |
c = 16.9192 (8) Å | T = 150 K |
β = 106.6952 (11)° | Block, colorless |
V = 6945.0 (5) Å3 | 0.27 × 0.20 × 0.16 mm |
Z = 8 |
Bruker SMART APEX CCD area-detector diffractometer | 15924 independent reflections |
Radiation source: fine-focus sealed tube | 11520 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 27.5°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −28→18 |
Tmin = 0.680, Tmax = 0.790 | k = −25→22 |
40984 measured reflections | l = −21→21 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.033P)2 + 0.398P] where P = (Fo2 + 2Fc2)/3 |
15924 reflections | (Δ/σ)max = 0.003 |
829 parameters | Δρmax = 1.35 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
[Pd(C4H3N2)I(C18H15P)2] | V = 6945.0 (5) Å3 |
Mr = 836.92 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 21.5786 (9) Å | µ = 1.55 mm−1 |
b = 19.8596 (9) Å | T = 150 K |
c = 16.9192 (8) Å | 0.27 × 0.20 × 0.16 mm |
β = 106.6952 (11)° |
Bruker SMART APEX CCD area-detector diffractometer | 15924 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 11520 reflections with I > 2σ(I) |
Tmin = 0.680, Tmax = 0.790 | Rint = 0.055 |
40984 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.04 | Δρmax = 1.35 e Å−3 |
15924 reflections | Δρmin = −0.55 e Å−3 |
829 parameters |
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 | ||
Pd1 | 0.146035 (15) | 0.406204 (16) | 0.895828 (18) | 0.01645 (8) | |
I1 | 0.089411 (14) | 0.285212 (15) | 0.898708 (18) | 0.02538 (8) | |
P1 | 0.23255 (5) | 0.37985 (6) | 1.01093 (6) | 0.0168 (2) | |
P2 | 0.05913 (5) | 0.44510 (6) | 0.78820 (7) | 0.0195 (2) | |
N1 | 0.17522 (18) | 0.54643 (19) | 0.9394 (2) | 0.0253 (9) | |
N2 | 0.25835 (19) | 0.5641 (2) | 0.8410 (2) | 0.0319 (10) | |
C1 | 0.18713 (19) | 0.4964 (2) | 0.8938 (2) | 0.0193 (9) | |
C2 | 0.2052 (2) | 0.6052 (2) | 0.9359 (3) | 0.0298 (11) | |
H2 | 0.1979 | 0.6421 | 0.9680 | 0.036* | |
C3 | 0.2459 (2) | 0.6137 (2) | 0.8876 (3) | 0.0339 (12) | |
H3 | 0.2659 | 0.6562 | 0.8872 | 0.041* | |
C4 | 0.2281 (2) | 0.5069 (2) | 0.8446 (3) | 0.0242 (10) | |
H4 | 0.2347 | 0.4706 | 0.8114 | 0.029* | |
C5 | 0.2836 (2) | 0.4508 (2) | 1.0597 (3) | 0.0214 (10) | |
C6 | 0.3266 (2) | 0.4770 (2) | 1.0200 (3) | 0.0255 (10) | |
H6 | 0.3328 | 0.4549 | 0.9731 | 0.031* | |
C7 | 0.3607 (2) | 0.5359 (2) | 1.0495 (3) | 0.0357 (13) | |
H7 | 0.3898 | 0.5539 | 1.0223 | 0.043* | |
C8 | 0.3524 (3) | 0.5679 (3) | 1.1180 (3) | 0.0419 (14) | |
H8 | 0.3754 | 0.6082 | 1.1377 | 0.050* | |
C9 | 0.3109 (3) | 0.5415 (3) | 1.1574 (3) | 0.0415 (14) | |
H9 | 0.3058 | 0.5633 | 1.2051 | 0.050* | |
C10 | 0.2760 (2) | 0.4833 (2) | 1.1288 (3) | 0.0314 (11) | |
H10 | 0.2470 | 0.4658 | 1.1565 | 0.038* | |
C11 | 0.2050 (2) | 0.3462 (2) | 1.0950 (2) | 0.0181 (9) | |
C12 | 0.1520 (2) | 0.3765 (2) | 1.1116 (3) | 0.0278 (11) | |
H12 | 0.1295 | 0.4117 | 1.0770 | 0.033* | |
C13 | 0.1320 (2) | 0.3558 (2) | 1.1782 (3) | 0.0309 (11) | |
H13 | 0.0967 | 0.3779 | 1.1901 | 0.037* | |
C14 | 0.1626 (2) | 0.3036 (2) | 1.2273 (3) | 0.0304 (12) | |
H14 | 0.1484 | 0.2897 | 1.2729 | 0.036* | |
C15 | 0.2141 (2) | 0.2713 (2) | 1.2104 (3) | 0.0310 (12) | |
H15 | 0.2344 | 0.2343 | 1.2433 | 0.037* | |
C16 | 0.2363 (2) | 0.2931 (2) | 1.1448 (3) | 0.0236 (10) | |
H16 | 0.2725 | 0.2718 | 1.1341 | 0.028* | |
C17 | 0.2913 (2) | 0.3187 (2) | 0.9962 (2) | 0.0197 (9) | |
C18 | 0.2746 (2) | 0.2741 (2) | 0.9303 (3) | 0.0252 (10) | |
H18 | 0.2327 | 0.2758 | 0.8921 | 0.030* | |
C19 | 0.3193 (2) | 0.2269 (2) | 0.9201 (3) | 0.0320 (12) | |
H19 | 0.3078 | 0.1966 | 0.8748 | 0.038* | |
C20 | 0.3802 (2) | 0.2238 (2) | 0.9754 (3) | 0.0321 (12) | |
H20 | 0.4104 | 0.1914 | 0.9680 | 0.038* | |
C21 | 0.3972 (2) | 0.2672 (2) | 1.0407 (3) | 0.0285 (11) | |
H21 | 0.4392 | 0.2650 | 1.0787 | 0.034* | |
C22 | 0.3530 (2) | 0.3145 (2) | 1.0515 (3) | 0.0261 (10) | |
H22 | 0.3650 | 0.3444 | 1.0972 | 0.031* | |
C23 | 0.0450 (2) | 0.4064 (2) | 0.6870 (2) | 0.0206 (9) | |
C24 | 0.0775 (2) | 0.3482 (2) | 0.6767 (3) | 0.0274 (11) | |
H24 | 0.1054 | 0.3262 | 0.7233 | 0.033* | |
C25 | 0.0692 (2) | 0.3222 (2) | 0.5983 (3) | 0.0279 (11) | |
H25 | 0.0918 | 0.2825 | 0.5918 | 0.034* | |
C26 | 0.0291 (2) | 0.3527 (2) | 0.5299 (3) | 0.0309 (11) | |
H26 | 0.0238 | 0.3341 | 0.4766 | 0.037* | |
C27 | −0.0038 (2) | 0.4113 (3) | 0.5392 (3) | 0.0311 (12) | |
H27 | −0.0317 | 0.4329 | 0.4922 | 0.037* | |
C28 | 0.0044 (2) | 0.4376 (2) | 0.6168 (3) | 0.0262 (10) | |
H28 | −0.0179 | 0.4776 | 0.6229 | 0.031* | |
C29 | 0.0602 (2) | 0.5342 (2) | 0.7604 (3) | 0.0228 (10) | |
C30 | 0.0258 (2) | 0.5822 (2) | 0.7892 (3) | 0.0315 (12) | |
H30 | 0.0006 | 0.5693 | 0.8245 | 0.038* | |
C31 | 0.0279 (2) | 0.6497 (3) | 0.7667 (4) | 0.0439 (14) | |
H31 | 0.0039 | 0.6828 | 0.7859 | 0.053* | |
C32 | 0.0657 (3) | 0.6677 (3) | 0.7156 (4) | 0.0460 (15) | |
H32 | 0.0668 | 0.7133 | 0.6991 | 0.055* | |
C33 | 0.1010 (2) | 0.6209 (3) | 0.6892 (3) | 0.0378 (13) | |
H33 | 0.1277 | 0.6340 | 0.6559 | 0.045* | |
C34 | 0.0982 (2) | 0.5543 (2) | 0.7106 (3) | 0.0310 (11) | |
H34 | 0.1225 | 0.5217 | 0.6912 | 0.037* | |
C35 | −0.0150 (2) | 0.4370 (2) | 0.8193 (3) | 0.0212 (10) | |
C36 | −0.0760 (2) | 0.4286 (2) | 0.7642 (3) | 0.0320 (12) | |
H36 | −0.0808 | 0.4256 | 0.7067 | 0.038* | |
C37 | −0.1299 (2) | 0.4245 (3) | 0.7925 (3) | 0.0398 (14) | |
H37 | −0.1714 | 0.4186 | 0.7543 | 0.048* | |
C38 | −0.1241 (2) | 0.4289 (2) | 0.8757 (3) | 0.0339 (12) | |
H38 | −0.1613 | 0.4258 | 0.8948 | 0.041* | |
C39 | −0.0640 (2) | 0.4378 (2) | 0.9306 (3) | 0.0340 (12) | |
H39 | −0.0598 | 0.4419 | 0.9879 | 0.041* | |
C40 | −0.0094 (2) | 0.4408 (2) | 0.9030 (3) | 0.0291 (11) | |
H40 | 0.0321 | 0.4456 | 0.9417 | 0.035* | |
Pd2 | 0.348046 (15) | 0.592426 (16) | 0.622033 (18) | 0.01642 (8) | |
I2 | 0.406173 (15) | 0.713311 (15) | 0.626859 (18) | 0.02865 (8) | |
P3 | 0.42975 (5) | 0.55229 (6) | 0.73396 (7) | 0.0190 (2) | |
P4 | 0.27144 (6) | 0.61773 (6) | 0.49785 (7) | 0.0207 (3) | |
N3 | 0.32016 (18) | 0.45176 (18) | 0.5822 (2) | 0.0247 (9) | |
N4 | 0.21891 (19) | 0.4440 (2) | 0.6553 (2) | 0.0313 (10) | |
C41 | 0.3031 (2) | 0.5044 (2) | 0.6191 (2) | 0.0176 (9) | |
C42 | 0.2857 (2) | 0.3946 (2) | 0.5807 (3) | 0.0306 (11) | |
H42 | 0.2967 | 0.3555 | 0.5553 | 0.037* | |
C43 | 0.2350 (2) | 0.3918 (2) | 0.6152 (3) | 0.0334 (12) | |
H43 | 0.2107 | 0.3513 | 0.6104 | 0.040* | |
C44 | 0.2532 (2) | 0.4990 (2) | 0.6557 (3) | 0.0240 (10) | |
H44 | 0.2432 | 0.5376 | 0.6829 | 0.029* | |
C45 | 0.4259 (2) | 0.4636 (2) | 0.7618 (2) | 0.0206 (9) | |
C46 | 0.4659 (2) | 0.4140 (2) | 0.7458 (3) | 0.0302 (11) | |
H46 | 0.4995 | 0.4258 | 0.7224 | 0.036* | |
C47 | 0.4572 (2) | 0.3475 (2) | 0.7640 (3) | 0.0368 (12) | |
H47 | 0.4844 | 0.3137 | 0.7522 | 0.044* | |
C48 | 0.4096 (2) | 0.3298 (2) | 0.7987 (3) | 0.0339 (12) | |
H48 | 0.4039 | 0.2840 | 0.8111 | 0.041* | |
C49 | 0.3701 (3) | 0.3784 (3) | 0.8156 (3) | 0.0344 (12) | |
H49 | 0.3369 | 0.3661 | 0.8396 | 0.041* | |
C50 | 0.3784 (2) | 0.4451 (2) | 0.7979 (2) | 0.0249 (10) | |
H50 | 0.3513 | 0.4786 | 0.8106 | 0.030* | |
C51 | 0.4455 (2) | 0.5931 (2) | 0.8343 (2) | 0.0190 (9) | |
C52 | 0.4094 (2) | 0.6479 (2) | 0.8460 (3) | 0.0252 (10) | |
H52 | 0.3764 | 0.6657 | 0.8009 | 0.030* | |
C53 | 0.4213 (2) | 0.6768 (2) | 0.9234 (3) | 0.0278 (11) | |
H53 | 0.3966 | 0.7146 | 0.9311 | 0.033* | |
C54 | 0.4686 (2) | 0.6513 (2) | 0.9892 (3) | 0.0260 (10) | |
H54 | 0.4764 | 0.6713 | 1.0421 | 0.031* | |
C55 | 0.5049 (2) | 0.5964 (2) | 0.9783 (3) | 0.0273 (11) | |
H55 | 0.5378 | 0.5789 | 1.0237 | 0.033* | |
C56 | 0.4931 (2) | 0.5671 (2) | 0.9016 (3) | 0.0240 (10) | |
H56 | 0.5176 | 0.5291 | 0.8944 | 0.029* | |
C57 | 0.5029 (2) | 0.5600 (2) | 0.7017 (3) | 0.0220 (10) | |
C58 | 0.5026 (2) | 0.5306 (2) | 0.6273 (3) | 0.0334 (12) | |
H58 | 0.4662 | 0.5053 | 0.5968 | 0.040* | |
C59 | 0.5559 (2) | 0.5383 (2) | 0.5973 (3) | 0.0369 (13) | |
H59 | 0.5557 | 0.5178 | 0.5465 | 0.044* | |
C60 | 0.6084 (2) | 0.5750 (3) | 0.6400 (3) | 0.0349 (12) | |
H60 | 0.6446 | 0.5801 | 0.6193 | 0.042* | |
C61 | 0.6082 (2) | 0.6047 (3) | 0.7135 (3) | 0.0402 (13) | |
H61 | 0.6445 | 0.6305 | 0.7433 | 0.048* | |
C62 | 0.5558 (2) | 0.5974 (3) | 0.7447 (3) | 0.0362 (12) | |
H62 | 0.5563 | 0.6180 | 0.7955 | 0.043* | |
C63 | 0.3096 (2) | 0.6476 (2) | 0.4213 (3) | 0.0266 (11) | |
C64 | 0.2779 (3) | 0.6866 (3) | 0.3541 (3) | 0.0487 (16) | |
H64 | 0.2354 | 0.7027 | 0.3480 | 0.058* | |
C65 | 0.3104 (4) | 0.7020 (3) | 0.2948 (3) | 0.062 (2) | |
H65 | 0.2892 | 0.7283 | 0.2480 | 0.074* | |
C66 | 0.3709 (4) | 0.6800 (3) | 0.3034 (4) | 0.065 (2) | |
H66 | 0.3918 | 0.6911 | 0.2627 | 0.077* | |
C67 | 0.4028 (4) | 0.6415 (3) | 0.3702 (4) | 0.062 (2) | |
H67 | 0.4456 | 0.6261 | 0.3762 | 0.074* | |
C68 | 0.3716 (3) | 0.6258 (3) | 0.4285 (3) | 0.0420 (14) | |
H68 | 0.3934 | 0.5991 | 0.4748 | 0.050* | |
C69 | 0.2243 (2) | 0.5458 (2) | 0.4453 (3) | 0.0244 (10) | |
C70 | 0.2445 (2) | 0.5079 (2) | 0.3884 (3) | 0.0293 (11) | |
H70 | 0.2804 | 0.5223 | 0.3709 | 0.035* | |
C71 | 0.2121 (3) | 0.4490 (2) | 0.3572 (3) | 0.0362 (12) | |
H71 | 0.2249 | 0.4242 | 0.3165 | 0.043* | |
C72 | 0.1617 (2) | 0.4261 (3) | 0.3847 (3) | 0.0363 (13) | |
H72 | 0.1411 | 0.3848 | 0.3644 | 0.044* | |
C73 | 0.1411 (2) | 0.4625 (2) | 0.4409 (3) | 0.0313 (11) | |
H73 | 0.1058 | 0.4469 | 0.4591 | 0.038* | |
C74 | 0.1723 (2) | 0.5227 (2) | 0.4716 (3) | 0.0270 (11) | |
H74 | 0.1581 | 0.5482 | 0.5106 | 0.032* | |
C75 | 0.2096 (2) | 0.6772 (2) | 0.5041 (3) | 0.0263 (11) | |
C76 | 0.2169 (2) | 0.7142 (2) | 0.5748 (3) | 0.0320 (11) | |
H76 | 0.2556 | 0.7101 | 0.6188 | 0.038* | |
C77 | 0.1684 (3) | 0.7577 (3) | 0.5833 (4) | 0.0449 (14) | |
H77 | 0.1743 | 0.7831 | 0.6325 | 0.054* | |
C78 | 0.1129 (3) | 0.7634 (3) | 0.5207 (4) | 0.0504 (17) | |
H78 | 0.0794 | 0.7921 | 0.5272 | 0.061* | |
C79 | 0.1040 (3) | 0.7285 (3) | 0.4484 (4) | 0.0503 (16) | |
H79 | 0.0653 | 0.7340 | 0.4047 | 0.060* | |
C80 | 0.1521 (2) | 0.6850 (2) | 0.4392 (3) | 0.0405 (13) | |
H80 | 0.1462 | 0.6606 | 0.3893 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.01639 (17) | 0.01662 (18) | 0.01584 (16) | −0.00067 (13) | 0.00386 (13) | 0.00095 (13) |
I1 | 0.02899 (17) | 0.02145 (17) | 0.02611 (16) | −0.00769 (13) | 0.00859 (13) | −0.00107 (12) |
P1 | 0.0177 (6) | 0.0164 (6) | 0.0164 (5) | −0.0003 (5) | 0.0049 (4) | −0.0006 (4) |
P2 | 0.0185 (6) | 0.0211 (6) | 0.0179 (5) | 0.0031 (5) | 0.0037 (5) | 0.0004 (5) |
N1 | 0.026 (2) | 0.025 (2) | 0.027 (2) | 0.0014 (17) | 0.0101 (17) | −0.0026 (17) |
N2 | 0.032 (2) | 0.034 (3) | 0.033 (2) | −0.010 (2) | 0.0145 (19) | 0.0015 (19) |
C1 | 0.014 (2) | 0.024 (3) | 0.018 (2) | 0.0027 (18) | 0.0016 (17) | 0.0060 (18) |
C2 | 0.030 (3) | 0.019 (3) | 0.042 (3) | 0.005 (2) | 0.012 (2) | −0.008 (2) |
C3 | 0.041 (3) | 0.020 (3) | 0.043 (3) | −0.005 (2) | 0.016 (3) | 0.004 (2) |
C4 | 0.025 (2) | 0.025 (3) | 0.026 (2) | −0.003 (2) | 0.013 (2) | −0.0016 (19) |
C5 | 0.022 (2) | 0.017 (2) | 0.022 (2) | 0.0007 (19) | 0.0012 (19) | 0.0017 (18) |
C6 | 0.024 (3) | 0.020 (3) | 0.032 (3) | 0.002 (2) | 0.007 (2) | 0.003 (2) |
C7 | 0.021 (3) | 0.029 (3) | 0.055 (3) | −0.007 (2) | 0.008 (2) | 0.011 (3) |
C8 | 0.040 (3) | 0.024 (3) | 0.054 (4) | −0.009 (2) | 0.002 (3) | −0.003 (3) |
C9 | 0.049 (4) | 0.027 (3) | 0.043 (3) | −0.004 (3) | 0.005 (3) | −0.011 (2) |
C10 | 0.035 (3) | 0.024 (3) | 0.033 (3) | −0.003 (2) | 0.006 (2) | −0.003 (2) |
C11 | 0.020 (2) | 0.020 (2) | 0.015 (2) | −0.0062 (18) | 0.0066 (17) | −0.0005 (17) |
C12 | 0.026 (3) | 0.031 (3) | 0.026 (2) | 0.001 (2) | 0.007 (2) | 0.004 (2) |
C13 | 0.033 (3) | 0.038 (3) | 0.028 (3) | −0.003 (2) | 0.017 (2) | −0.003 (2) |
C14 | 0.046 (3) | 0.028 (3) | 0.022 (2) | −0.013 (2) | 0.017 (2) | −0.007 (2) |
C15 | 0.048 (3) | 0.020 (3) | 0.022 (2) | −0.009 (2) | 0.007 (2) | 0.0019 (19) |
C16 | 0.031 (3) | 0.021 (3) | 0.020 (2) | −0.004 (2) | 0.0088 (19) | −0.0005 (18) |
C17 | 0.020 (2) | 0.021 (2) | 0.021 (2) | −0.0027 (19) | 0.0111 (18) | 0.0019 (18) |
C18 | 0.025 (3) | 0.025 (3) | 0.026 (2) | 0.000 (2) | 0.008 (2) | −0.0002 (19) |
C19 | 0.036 (3) | 0.031 (3) | 0.029 (3) | 0.005 (2) | 0.010 (2) | −0.006 (2) |
C20 | 0.034 (3) | 0.022 (3) | 0.044 (3) | 0.010 (2) | 0.019 (2) | 0.006 (2) |
C21 | 0.020 (2) | 0.028 (3) | 0.036 (3) | 0.000 (2) | 0.006 (2) | 0.004 (2) |
C22 | 0.022 (3) | 0.022 (3) | 0.032 (3) | 0.003 (2) | 0.003 (2) | −0.004 (2) |
C23 | 0.020 (2) | 0.025 (3) | 0.017 (2) | 0.0019 (19) | 0.0054 (18) | 0.0005 (18) |
C24 | 0.029 (3) | 0.028 (3) | 0.024 (2) | 0.004 (2) | 0.005 (2) | 0.003 (2) |
C25 | 0.025 (3) | 0.032 (3) | 0.026 (2) | 0.007 (2) | 0.007 (2) | −0.001 (2) |
C26 | 0.031 (3) | 0.041 (3) | 0.023 (2) | −0.004 (2) | 0.010 (2) | −0.003 (2) |
C27 | 0.028 (3) | 0.043 (3) | 0.020 (2) | 0.001 (2) | 0.002 (2) | 0.007 (2) |
C28 | 0.022 (2) | 0.029 (3) | 0.029 (3) | 0.005 (2) | 0.008 (2) | 0.001 (2) |
C29 | 0.018 (2) | 0.023 (3) | 0.024 (2) | −0.0015 (19) | −0.0011 (18) | 0.0039 (18) |
C30 | 0.025 (3) | 0.028 (3) | 0.043 (3) | 0.004 (2) | 0.012 (2) | 0.001 (2) |
C31 | 0.032 (3) | 0.028 (3) | 0.069 (4) | 0.010 (2) | 0.011 (3) | −0.002 (3) |
C32 | 0.039 (3) | 0.030 (3) | 0.062 (4) | 0.006 (3) | 0.004 (3) | 0.016 (3) |
C33 | 0.037 (3) | 0.034 (3) | 0.041 (3) | −0.004 (2) | 0.008 (2) | 0.013 (2) |
C34 | 0.031 (3) | 0.030 (3) | 0.029 (3) | −0.002 (2) | 0.005 (2) | 0.004 (2) |
C35 | 0.020 (2) | 0.020 (2) | 0.024 (2) | 0.0007 (19) | 0.0077 (19) | −0.0015 (18) |
C36 | 0.028 (3) | 0.041 (3) | 0.025 (2) | −0.005 (2) | 0.005 (2) | 0.006 (2) |
C37 | 0.021 (3) | 0.056 (4) | 0.039 (3) | −0.004 (2) | 0.004 (2) | 0.012 (3) |
C38 | 0.033 (3) | 0.028 (3) | 0.046 (3) | 0.002 (2) | 0.020 (3) | 0.005 (2) |
C39 | 0.045 (3) | 0.033 (3) | 0.029 (3) | 0.003 (2) | 0.019 (2) | −0.004 (2) |
C40 | 0.021 (3) | 0.039 (3) | 0.027 (2) | 0.002 (2) | 0.007 (2) | −0.007 (2) |
Pd2 | 0.01819 (17) | 0.01557 (18) | 0.01483 (15) | −0.00133 (14) | 0.00368 (13) | 0.00039 (13) |
I2 | 0.03742 (19) | 0.02015 (17) | 0.02770 (16) | −0.01020 (14) | 0.00826 (14) | −0.00112 (12) |
P3 | 0.0172 (6) | 0.0191 (6) | 0.0185 (5) | −0.0013 (5) | 0.0018 (5) | 0.0001 (4) |
P4 | 0.0252 (6) | 0.0162 (6) | 0.0185 (6) | −0.0011 (5) | 0.0028 (5) | 0.0007 (4) |
N3 | 0.030 (2) | 0.019 (2) | 0.025 (2) | 0.0029 (17) | 0.0068 (17) | 0.0002 (16) |
N4 | 0.034 (2) | 0.029 (2) | 0.032 (2) | −0.0095 (19) | 0.0102 (19) | 0.0030 (18) |
C41 | 0.020 (2) | 0.016 (2) | 0.014 (2) | −0.0028 (18) | 0.0014 (17) | 0.0031 (16) |
C42 | 0.046 (3) | 0.015 (3) | 0.028 (3) | 0.000 (2) | 0.006 (2) | 0.0018 (19) |
C43 | 0.040 (3) | 0.024 (3) | 0.032 (3) | −0.012 (2) | 0.002 (2) | 0.007 (2) |
C44 | 0.028 (3) | 0.025 (3) | 0.020 (2) | −0.002 (2) | 0.0084 (19) | 0.0039 (19) |
C45 | 0.022 (2) | 0.018 (2) | 0.018 (2) | 0.0000 (19) | −0.0003 (18) | −0.0004 (17) |
C46 | 0.027 (3) | 0.024 (3) | 0.039 (3) | 0.003 (2) | 0.009 (2) | 0.006 (2) |
C47 | 0.039 (3) | 0.026 (3) | 0.042 (3) | 0.012 (2) | 0.008 (3) | 0.003 (2) |
C48 | 0.041 (3) | 0.022 (3) | 0.033 (3) | −0.001 (2) | 0.002 (2) | 0.004 (2) |
C49 | 0.041 (3) | 0.034 (3) | 0.026 (3) | −0.009 (2) | 0.007 (2) | 0.002 (2) |
C50 | 0.031 (3) | 0.026 (3) | 0.017 (2) | −0.001 (2) | 0.0050 (19) | 0.0016 (18) |
C51 | 0.020 (2) | 0.017 (2) | 0.018 (2) | 0.0002 (18) | 0.0029 (17) | −0.0016 (17) |
C52 | 0.024 (3) | 0.024 (3) | 0.026 (2) | 0.002 (2) | 0.004 (2) | 0.0033 (19) |
C53 | 0.037 (3) | 0.021 (3) | 0.026 (2) | −0.003 (2) | 0.012 (2) | −0.002 (2) |
C54 | 0.029 (3) | 0.030 (3) | 0.020 (2) | −0.005 (2) | 0.008 (2) | −0.0019 (19) |
C55 | 0.025 (3) | 0.033 (3) | 0.021 (2) | −0.002 (2) | 0.0024 (19) | 0.007 (2) |
C56 | 0.021 (2) | 0.024 (3) | 0.027 (2) | 0.003 (2) | 0.006 (2) | 0.0034 (19) |
C57 | 0.017 (2) | 0.023 (3) | 0.025 (2) | 0.0007 (19) | 0.0046 (19) | 0.0010 (19) |
C58 | 0.029 (3) | 0.036 (3) | 0.037 (3) | −0.003 (2) | 0.013 (2) | −0.008 (2) |
C59 | 0.043 (3) | 0.035 (3) | 0.040 (3) | 0.002 (3) | 0.024 (3) | −0.008 (2) |
C60 | 0.024 (3) | 0.036 (3) | 0.049 (3) | 0.003 (2) | 0.017 (2) | 0.011 (2) |
C61 | 0.028 (3) | 0.051 (4) | 0.040 (3) | −0.013 (3) | 0.007 (2) | 0.003 (3) |
C62 | 0.033 (3) | 0.046 (3) | 0.028 (3) | −0.012 (3) | 0.007 (2) | −0.004 (2) |
C63 | 0.042 (3) | 0.019 (2) | 0.017 (2) | −0.008 (2) | 0.006 (2) | −0.0005 (18) |
C64 | 0.068 (4) | 0.044 (4) | 0.025 (3) | −0.028 (3) | −0.002 (3) | 0.009 (2) |
C65 | 0.098 (6) | 0.051 (4) | 0.024 (3) | −0.046 (4) | −0.001 (3) | 0.005 (3) |
C66 | 0.123 (7) | 0.049 (4) | 0.034 (3) | −0.044 (4) | 0.041 (4) | −0.018 (3) |
C67 | 0.104 (6) | 0.035 (4) | 0.072 (5) | −0.011 (4) | 0.066 (4) | −0.012 (3) |
C68 | 0.068 (4) | 0.026 (3) | 0.043 (3) | −0.001 (3) | 0.034 (3) | 0.001 (2) |
C69 | 0.027 (3) | 0.022 (3) | 0.019 (2) | −0.001 (2) | −0.0001 (19) | 0.0010 (18) |
C70 | 0.033 (3) | 0.029 (3) | 0.023 (2) | −0.003 (2) | 0.003 (2) | −0.003 (2) |
C71 | 0.047 (3) | 0.029 (3) | 0.031 (3) | −0.003 (3) | 0.009 (2) | −0.011 (2) |
C72 | 0.040 (3) | 0.024 (3) | 0.037 (3) | −0.010 (2) | −0.001 (2) | −0.004 (2) |
C73 | 0.026 (3) | 0.028 (3) | 0.036 (3) | −0.002 (2) | 0.003 (2) | 0.004 (2) |
C74 | 0.026 (3) | 0.024 (3) | 0.027 (2) | 0.002 (2) | 0.002 (2) | 0.001 (2) |
C75 | 0.022 (2) | 0.015 (2) | 0.038 (3) | −0.0052 (19) | 0.001 (2) | 0.001 (2) |
C76 | 0.033 (3) | 0.024 (3) | 0.041 (3) | 0.001 (2) | 0.013 (2) | −0.002 (2) |
C77 | 0.050 (4) | 0.029 (3) | 0.062 (4) | 0.007 (3) | 0.027 (3) | 0.000 (3) |
C78 | 0.038 (3) | 0.022 (3) | 0.098 (5) | 0.007 (3) | 0.029 (4) | 0.013 (3) |
C79 | 0.030 (3) | 0.032 (4) | 0.079 (5) | 0.002 (3) | 0.000 (3) | 0.015 (3) |
C80 | 0.036 (3) | 0.020 (3) | 0.056 (3) | −0.001 (2) | −0.003 (3) | 0.005 (2) |
Pd1—C1 | 2.003 (4) | Pd2—C41 | 1.992 (4) |
Pd1—P1 | 2.3373 (11) | Pd2—P4 | 2.3246 (12) |
Pd1—P2 | 2.3383 (11) | Pd2—P3 | 2.3263 (11) |
Pd1—I1 | 2.7025 (4) | Pd2—I2 | 2.6990 (4) |
P1—C11 | 1.820 (4) | P3—C57 | 1.819 (4) |
P1—C17 | 1.823 (4) | P3—C51 | 1.823 (4) |
P1—C5 | 1.832 (4) | P3—C45 | 1.832 (4) |
P2—C23 | 1.821 (4) | P4—C75 | 1.807 (5) |
P2—C35 | 1.829 (4) | P4—C63 | 1.822 (5) |
P2—C29 | 1.833 (4) | P4—C69 | 1.829 (4) |
N1—C1 | 1.328 (5) | N3—C41 | 1.324 (5) |
N1—C2 | 1.344 (6) | N3—C42 | 1.353 (6) |
N2—C4 | 1.321 (5) | N4—C44 | 1.319 (5) |
N2—C3 | 1.335 (6) | N4—C43 | 1.338 (6) |
C1—C4 | 1.394 (5) | C41—C44 | 1.391 (6) |
C2—C3 | 1.372 (6) | C42—C43 | 1.382 (7) |
C2—H2 | 0.9500 | C42—H42 | 0.9500 |
C3—H3 | 0.9500 | C43—H43 | 0.9500 |
C4—H4 | 0.9500 | C44—H44 | 0.9500 |
C5—C10 | 1.386 (6) | C45—C50 | 1.384 (6) |
C5—C6 | 1.393 (6) | C45—C46 | 1.387 (6) |
C6—C7 | 1.394 (6) | C46—C47 | 1.382 (6) |
C6—H6 | 0.9500 | C46—H46 | 0.9500 |
C7—C8 | 1.378 (7) | C47—C48 | 1.368 (7) |
C7—H7 | 0.9500 | C47—H47 | 0.9500 |
C8—C9 | 1.364 (7) | C48—C49 | 1.371 (7) |
C8—H8 | 0.9500 | C48—H48 | 0.9500 |
C9—C10 | 1.390 (6) | C49—C50 | 1.382 (6) |
C9—H9 | 0.9500 | C49—H49 | 0.9500 |
C10—H10 | 0.9500 | C50—H50 | 0.9500 |
C11—C12 | 1.389 (6) | C51—C52 | 1.386 (6) |
C11—C16 | 1.397 (6) | C51—C56 | 1.395 (6) |
C12—C13 | 1.379 (6) | C52—C53 | 1.385 (6) |
C12—H12 | 0.9500 | C52—H52 | 0.9500 |
C13—C14 | 1.373 (6) | C53—C54 | 1.372 (6) |
C13—H13 | 0.9500 | C53—H53 | 0.9500 |
C14—C15 | 1.382 (7) | C54—C55 | 1.386 (6) |
C14—H14 | 0.9500 | C54—H54 | 0.9500 |
C15—C16 | 1.397 (6) | C55—C56 | 1.377 (6) |
C15—H15 | 0.9500 | C55—H55 | 0.9500 |
C16—H16 | 0.9500 | C56—H56 | 0.9500 |
C17—C18 | 1.388 (6) | C57—C62 | 1.380 (6) |
C17—C22 | 1.393 (6) | C57—C58 | 1.387 (6) |
C18—C19 | 1.389 (6) | C58—C59 | 1.391 (6) |
C18—H18 | 0.9500 | C58—H58 | 0.9500 |
C19—C20 | 1.377 (7) | C59—C60 | 1.366 (7) |
C19—H19 | 0.9500 | C59—H59 | 0.9500 |
C20—C21 | 1.366 (6) | C60—C61 | 1.377 (7) |
C20—H20 | 0.9500 | C60—H60 | 0.9500 |
C21—C22 | 1.388 (6) | C61—C62 | 1.386 (6) |
C21—H21 | 0.9500 | C61—H61 | 0.9500 |
C22—H22 | 0.9500 | C62—H62 | 0.9500 |
C23—C24 | 1.389 (6) | C63—C68 | 1.378 (7) |
C23—C28 | 1.401 (6) | C63—C64 | 1.383 (6) |
C24—C25 | 1.385 (6) | C64—C65 | 1.412 (8) |
C24—H24 | 0.9500 | C64—H64 | 0.9500 |
C25—C26 | 1.371 (6) | C65—C66 | 1.344 (9) |
C25—H25 | 0.9500 | C65—H65 | 0.9500 |
C26—C27 | 1.396 (6) | C66—C67 | 1.375 (9) |
C26—H26 | 0.9500 | C66—H66 | 0.9500 |
C27—C28 | 1.377 (6) | C67—C68 | 1.382 (7) |
C27—H27 | 0.9500 | C67—H67 | 0.9500 |
C28—H28 | 0.9500 | C68—H68 | 0.9500 |
C29—C30 | 1.380 (6) | C69—C70 | 1.386 (6) |
C29—C34 | 1.392 (6) | C69—C74 | 1.398 (6) |
C30—C31 | 1.398 (7) | C70—C71 | 1.387 (6) |
C30—H30 | 0.9500 | C70—H70 | 0.9500 |
C31—C32 | 1.396 (7) | C71—C72 | 1.378 (7) |
C31—H31 | 0.9500 | C71—H71 | 0.9500 |
C32—C33 | 1.357 (7) | C72—C73 | 1.367 (7) |
C32—H32 | 0.9500 | C72—H72 | 0.9500 |
C33—C34 | 1.376 (6) | C73—C74 | 1.397 (6) |
C33—H33 | 0.9500 | C73—H73 | 0.9500 |
C34—H34 | 0.9500 | C74—H74 | 0.9500 |
C35—C40 | 1.388 (6) | C75—C76 | 1.375 (6) |
C35—C36 | 1.388 (6) | C75—C80 | 1.409 (6) |
C36—C37 | 1.381 (6) | C76—C77 | 1.394 (6) |
C36—H36 | 0.9500 | C76—H76 | 0.9500 |
C37—C38 | 1.380 (7) | C77—C78 | 1.357 (8) |
C37—H37 | 0.9500 | C77—H77 | 0.9500 |
C38—C39 | 1.372 (7) | C78—C79 | 1.372 (8) |
C38—H38 | 0.9500 | C78—H78 | 0.9500 |
C39—C40 | 1.388 (6) | C79—C80 | 1.393 (7) |
C39—H39 | 0.9500 | C79—H79 | 0.9500 |
C40—H40 | 0.9500 | C80—H80 | 0.9500 |
C1—Pd1—P1 | 87.86 (12) | C41—Pd2—P4 | 87.27 (12) |
C1—Pd1—P2 | 87.21 (12) | C41—Pd2—P3 | 88.26 (12) |
P1—Pd1—P2 | 173.12 (4) | P4—Pd2—P3 | 170.29 (4) |
C1—Pd1—I1 | 179.38 (12) | C41—Pd2—I2 | 178.44 (12) |
P1—Pd1—I1 | 92.46 (3) | P4—Pd2—I2 | 92.22 (3) |
P2—Pd1—I1 | 92.42 (3) | P3—Pd2—I2 | 92.47 (3) |
C11—P1—C17 | 105.01 (19) | C57—P3—C51 | 107.2 (2) |
C11—P1—C5 | 102.72 (19) | C57—P3—C45 | 105.4 (2) |
C17—P1—C5 | 102.8 (2) | C51—P3—C45 | 101.44 (19) |
C11—P1—Pd1 | 111.78 (14) | C57—P3—Pd2 | 104.32 (14) |
C17—P1—Pd1 | 117.08 (14) | C51—P3—Pd2 | 120.03 (14) |
C5—P1—Pd1 | 115.82 (14) | C45—P3—Pd2 | 117.31 (14) |
C23—P2—C35 | 108.0 (2) | C75—P4—C63 | 108.7 (2) |
C23—P2—C29 | 100.2 (2) | C75—P4—C69 | 102.8 (2) |
C35—P2—C29 | 103.6 (2) | C63—P4—C69 | 102.2 (2) |
C23—P2—Pd1 | 118.23 (14) | C75—P4—Pd2 | 115.70 (16) |
C35—P2—Pd1 | 108.57 (14) | C63—P4—Pd2 | 111.34 (16) |
C29—P2—Pd1 | 116.91 (14) | C69—P4—Pd2 | 114.98 (14) |
C1—N1—C2 | 116.7 (4) | C41—N3—C42 | 116.5 (4) |
C4—N2—C3 | 114.9 (4) | C44—N4—C43 | 114.6 (4) |
N1—C1—C4 | 119.8 (4) | N3—C41—C44 | 120.3 (4) |
N1—C1—Pd1 | 119.9 (3) | N3—C41—Pd2 | 120.4 (3) |
C4—C1—Pd1 | 120.3 (3) | C44—C41—Pd2 | 119.3 (3) |
N1—C2—C3 | 122.1 (4) | N3—C42—C43 | 121.6 (4) |
N1—C2—H2 | 119.0 | N3—C42—H42 | 119.2 |
C3—C2—H2 | 119.0 | C43—C42—H42 | 119.2 |
N2—C3—C2 | 122.3 (4) | N4—C43—C42 | 122.4 (4) |
N2—C3—H3 | 118.9 | N4—C43—H43 | 118.8 |
C2—C3—H3 | 118.9 | C42—C43—H43 | 118.8 |
N2—C4—C1 | 124.3 (4) | N4—C44—C41 | 124.5 (4) |
N2—C4—H4 | 117.8 | N4—C44—H44 | 117.7 |
C1—C4—H4 | 117.8 | C41—C44—H44 | 117.7 |
C10—C5—C6 | 119.3 (4) | C50—C45—C46 | 118.7 (4) |
C10—C5—P1 | 122.4 (4) | C50—C45—P3 | 117.5 (3) |
C6—C5—P1 | 117.9 (3) | C46—C45—P3 | 123.8 (3) |
C5—C6—C7 | 119.8 (4) | C47—C46—C45 | 120.2 (5) |
C5—C6—H6 | 120.1 | C47—C46—H46 | 119.9 |
C7—C6—H6 | 120.1 | C45—C46—H46 | 119.9 |
C8—C7—C6 | 120.4 (5) | C48—C47—C46 | 120.5 (5) |
C8—C7—H7 | 119.8 | C48—C47—H47 | 119.7 |
C6—C7—H7 | 119.8 | C46—C47—H47 | 119.7 |
C9—C8—C7 | 119.6 (5) | C47—C48—C49 | 119.9 (5) |
C9—C8—H8 | 120.2 | C47—C48—H48 | 120.1 |
C7—C8—H8 | 120.2 | C49—C48—H48 | 120.1 |
C8—C9—C10 | 121.1 (5) | C48—C49—C50 | 120.1 (5) |
C8—C9—H9 | 119.5 | C48—C49—H49 | 120.0 |
C10—C9—H9 | 119.5 | C50—C49—H49 | 120.0 |
C5—C10—C9 | 119.8 (5) | C49—C50—C45 | 120.6 (4) |
C5—C10—H10 | 120.1 | C49—C50—H50 | 119.7 |
C9—C10—H10 | 120.1 | C45—C50—H50 | 119.7 |
C12—C11—C16 | 119.3 (4) | C52—C51—C56 | 119.1 (4) |
C12—C11—P1 | 118.1 (3) | C52—C51—P3 | 121.4 (3) |
C16—C11—P1 | 122.5 (3) | C56—C51—P3 | 119.5 (3) |
C13—C12—C11 | 120.3 (4) | C53—C52—C51 | 120.1 (4) |
C13—C12—H12 | 119.9 | C53—C52—H52 | 119.9 |
C11—C12—H12 | 119.9 | C51—C52—H52 | 119.9 |
C14—C13—C12 | 120.7 (4) | C54—C53—C52 | 120.4 (4) |
C14—C13—H13 | 119.7 | C54—C53—H53 | 119.8 |
C12—C13—H13 | 119.7 | C52—C53—H53 | 119.8 |
C13—C14—C15 | 120.0 (4) | C53—C54—C55 | 120.0 (4) |
C13—C14—H14 | 120.0 | C53—C54—H54 | 120.0 |
C15—C14—H14 | 120.0 | C55—C54—H54 | 120.0 |
C14—C15—C16 | 120.0 (4) | C56—C55—C54 | 119.9 (4) |
C14—C15—H15 | 120.0 | C56—C55—H55 | 120.0 |
C16—C15—H15 | 120.0 | C54—C55—H55 | 120.0 |
C15—C16—C11 | 119.7 (4) | C55—C56—C51 | 120.4 (4) |
C15—C16—H16 | 120.2 | C55—C56—H56 | 119.8 |
C11—C16—H16 | 120.2 | C51—C56—H56 | 119.8 |
C18—C17—C22 | 118.6 (4) | C62—C57—C58 | 119.5 (4) |
C18—C17—P1 | 120.3 (3) | C62—C57—P3 | 123.0 (4) |
C22—C17—P1 | 121.1 (3) | C58—C57—P3 | 117.3 (4) |
C17—C18—C19 | 120.0 (4) | C57—C58—C59 | 119.7 (5) |
C17—C18—H18 | 120.0 | C57—C58—H58 | 120.2 |
C19—C18—H18 | 120.0 | C59—C58—H58 | 120.2 |
C20—C19—C18 | 120.5 (4) | C60—C59—C58 | 120.8 (5) |
C20—C19—H19 | 119.8 | C60—C59—H59 | 119.6 |
C18—C19—H19 | 119.8 | C58—C59—H59 | 119.6 |
C21—C20—C19 | 120.2 (4) | C59—C60—C61 | 119.3 (5) |
C21—C20—H20 | 119.9 | C59—C60—H60 | 120.4 |
C19—C20—H20 | 119.9 | C61—C60—H60 | 120.4 |
C20—C21—C22 | 119.9 (4) | C60—C61—C62 | 120.9 (5) |
C20—C21—H21 | 120.1 | C60—C61—H61 | 119.6 |
C22—C21—H21 | 120.1 | C62—C61—H61 | 119.6 |
C21—C22—C17 | 120.9 (4) | C57—C62—C61 | 119.8 (5) |
C21—C22—H22 | 119.6 | C57—C62—H62 | 120.1 |
C17—C22—H22 | 119.6 | C61—C62—H62 | 120.1 |
C24—C23—C28 | 118.5 (4) | C68—C63—C64 | 119.1 (5) |
C24—C23—P2 | 121.0 (3) | C68—C63—P4 | 117.3 (4) |
C28—C23—P2 | 120.3 (3) | C64—C63—P4 | 123.4 (4) |
C25—C24—C23 | 120.0 (4) | C63—C64—C65 | 118.4 (6) |
C25—C24—H24 | 120.0 | C63—C64—H64 | 120.8 |
C23—C24—H24 | 120.0 | C65—C64—H64 | 120.8 |
C26—C25—C24 | 121.3 (4) | C66—C65—C64 | 121.2 (6) |
C26—C25—H25 | 119.3 | C66—C65—H65 | 119.4 |
C24—C25—H25 | 119.3 | C64—C65—H65 | 119.4 |
C25—C26—C27 | 119.4 (4) | C65—C66—C67 | 120.7 (6) |
C25—C26—H26 | 120.3 | C65—C66—H66 | 119.6 |
C27—C26—H26 | 120.3 | C67—C66—H66 | 119.6 |
C28—C27—C26 | 119.6 (4) | C66—C67—C68 | 118.7 (6) |
C28—C27—H27 | 120.2 | C66—C67—H67 | 120.6 |
C26—C27—H27 | 120.2 | C68—C67—H67 | 120.6 |
C27—C28—C23 | 121.2 (4) | C63—C68—C67 | 121.7 (6) |
C27—C28—H28 | 119.4 | C63—C68—H68 | 119.1 |
C23—C28—H28 | 119.4 | C67—C68—H68 | 119.1 |
C30—C29—C34 | 119.1 (4) | C70—C69—C74 | 118.9 (4) |
C30—C29—P2 | 121.9 (4) | C70—C69—P4 | 121.3 (4) |
C34—C29—P2 | 119.0 (4) | C74—C69—P4 | 119.1 (3) |
C29—C30—C31 | 120.2 (5) | C69—C70—C71 | 119.8 (5) |
C29—C30—H30 | 119.9 | C69—C70—H70 | 120.1 |
C31—C30—H30 | 119.9 | C71—C70—H70 | 120.1 |
C32—C31—C30 | 119.0 (5) | C72—C71—C70 | 120.7 (5) |
C32—C31—H31 | 120.5 | C72—C71—H71 | 119.6 |
C30—C31—H31 | 120.5 | C70—C71—H71 | 119.6 |
C33—C32—C31 | 120.8 (5) | C73—C72—C71 | 120.4 (5) |
C33—C32—H32 | 119.6 | C73—C72—H72 | 119.8 |
C31—C32—H32 | 119.6 | C71—C72—H72 | 119.8 |
C32—C33—C34 | 120.0 (5) | C72—C73—C74 | 119.5 (5) |
C32—C33—H33 | 120.0 | C72—C73—H73 | 120.3 |
C34—C33—H33 | 120.0 | C74—C73—H73 | 120.3 |
C33—C34—C29 | 120.8 (5) | C73—C74—C69 | 120.6 (4) |
C33—C34—H34 | 119.6 | C73—C74—H74 | 119.7 |
C29—C34—H34 | 119.6 | C69—C74—H74 | 119.7 |
C40—C35—C36 | 118.6 (4) | C76—C75—C80 | 118.3 (5) |
C40—C35—P2 | 117.5 (3) | C76—C75—P4 | 119.9 (4) |
C36—C35—P2 | 123.8 (3) | C80—C75—P4 | 121.7 (4) |
C37—C36—C35 | 120.3 (4) | C75—C76—C77 | 121.3 (5) |
C37—C36—H36 | 119.8 | C75—C76—H76 | 119.4 |
C35—C36—H36 | 119.8 | C77—C76—H76 | 119.4 |
C38—C37—C36 | 120.8 (5) | C78—C77—C76 | 119.5 (5) |
C38—C37—H37 | 119.6 | C78—C77—H77 | 120.2 |
C36—C37—H37 | 119.6 | C76—C77—H77 | 120.2 |
C39—C38—C37 | 119.3 (5) | C77—C78—C79 | 121.3 (5) |
C39—C38—H38 | 120.3 | C77—C78—H78 | 119.4 |
C37—C38—H38 | 120.3 | C79—C78—H78 | 119.4 |
C38—C39—C40 | 120.4 (4) | C78—C79—C80 | 119.7 (5) |
C38—C39—H39 | 119.8 | C78—C79—H79 | 120.1 |
C40—C39—H39 | 119.8 | C80—C79—H79 | 120.1 |
C35—C40—C39 | 120.5 (4) | C79—C80—C75 | 119.9 (5) |
C35—C40—H40 | 119.7 | C79—C80—H80 | 120.0 |
C39—C40—H40 | 119.7 | C75—C80—H80 | 120.0 |
Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the C11–C16, C17–C22, C51–C56, C63–C68 and C75–C80 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg5i | 0.95 | 2.99 | 3.898 (5) | 160 |
C7—H7···Cg3 | 0.95 | 3.00 | 3.930 (5) | 168 |
C25—H25···Cg1ii | 0.95 | 2.91 | 3.769 (5) | 151 |
C42—H42···Cg2ii | 0.95 | 3.00 | 3.944 (5) | 176 |
C53—H53···Cg4i | 0.95 | 2.80 | 3.617 (5) | 145 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Pd(C4H3N2)I(C18H15P)2] |
Mr | 836.92 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 21.5786 (9), 19.8596 (9), 16.9192 (8) |
β (°) | 106.6952 (11) |
V (Å3) | 6945.0 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.55 |
Crystal size (mm) | 0.27 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.680, 0.790 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40984, 15924, 11520 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.101, 1.04 |
No. of reflections | 15924 |
No. of parameters | 829 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.35, −0.55 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the C11–C16, C17–C22, C51–C56, C63–C68 and C75–C80 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg5i | 0.95 | 2.99 | 3.898 (5) | 160 |
C7—H7···Cg3 | 0.95 | 3.00 | 3.930 (5) | 168 |
C25—H25···Cg1ii | 0.95 | 2.91 | 3.769 (5) | 151 |
C42—H42···Cg2ii | 0.95 | 3.00 | 3.944 (5) | 176 |
C53—H53···Cg4i | 0.95 | 2.80 | 3.617 (5) | 145 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
Acknowledgements
We thank the National Science Council of the Republic of China for financial support (NSC101–2113-M-241–001-MY3).
References
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Processes leading to the formation of C—C bonds and cathalized by Palladium complexes are among the most important reactions in organic synthesis (Dobrzynski & Angelici, 1975). Intramolecular reductive elimination of the 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 organoboronic acids and aryl bromides (Beeby, et al., 2004). Pyrazinyl nickel complexes have been used to as a catalyst for C—C coupling reactions (Steffen et al., 2005), but to our knowledge, no pyrazinyl palladium crystal structure has been described.
For the synthesis of the pyrazinyl title compound, complex [Pd(PPh3)4] was used to react with 2-iodopyrazine in dichloromethane at room temperature. As a result, a two triphenylphosphine displaced complex [Pd(I)(C4H3N2)(PPh3)2] was isolated with 98% yield. The X-ray crystal structure analysis has been carried out to provide structural parameters.
The molecular structure (with two independent molecules) is shown in Fig. 1. There are small difference in bond distances (in the range of 0.001–0.027 Å) and bond angles (in the range of 0.05–0.7.46°) between them, mainly around the metal atoms. The palladium atom has a distorted square planar geometry, while being displaced by 0.0549 (12) Å (0.0734 (13) Å) from the least-squares plane Angles around the Pd center lay within ± 2.79° of 90°. The average Pd—C1(C41) bond distance, 1.998 (4) Å, is longer than reported PdII-carbon(carbonyl) distances, and similar to those of Pd—C(carbene) distances (Cardin et al., 1972). The PPh3 ligands are in trans position: P—Pd—P(av), 171.71 (4)°, while the pyrazinyl ligand and iodine atom, also trans to each other, present a C—Pd—I(av) of 178.91 (12)°. The phosphorus atoms approach tetrahedral geometry as expected, with a maximun deviation from idealized tetrahedral geometry for C5—P1—Pd = 119.13 (14)°. The average Pd—N1(N(3) bond distance of 2.899 (4) Å indicates no bonding interaction between the nitrogen atom and palladium metal atom. Within the pyrazinyl ligand itself, the geometry is consistent with a significant partial double bond character in the C—C and C—N bond. The C—N(av) bond distances (1.321 (5), 1.353 (6) Å) are typical for a C—N bond having partial double bond character and are certainly much shorter than a normal C—N (1.47 Å) single bond. The average Pd—C (1.998 Å), Pd—P (2.3375, 2.3255 Å) and Pd—I (2.7007 Å) coordination lengths of (I) are in agreement with reported values (Yih et al., 2009).
There are five C—H···π intermolecular hydrogen bond interactions (Fig. 2 and Table 1) and intramolecular π-π interactions (Fig. 1). The pyrazinyl ligand (N1, N2, C1 > C4) and two phenyl rings (C5 > C10 and C29 > C34) from the trans triphenylphosphanes respectively are nearly parallel, with intercentroid distances of 3.564 (3) and 3.677 (3) Å, and a shortest inter-ring distance of 3.120 (2) and 3,317 (2) Å. A similar effect is observed in the remaining molecule, where the intercentroid distances between the pyrazinyl ligand (N3, N4, C41 > C44) and the phenyl rings (C45 > C50 and C69 > C74) are 3.716 (3) and 3.446 (3) Å, with a shortest inter-ring distance of 3.225 (2) and 3,119 (2) Å.