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The asymmetric unit of the title compound, μ-nitrato-bis­[(2,2′:6′,2′′-terpyridyl-κ3N)palladium(II)] hexa­kis(hexa­fluorido­phosphate) acetonitrile solvate, [Pd2(C15H11N3)2NO3]PF6·C2H3N, contains two cationic dimers, [Pd2(C15H11N3)2NO3]3+, six (PF6) anions and one CH3CN solvent mol­ecule. Each cationic dimer is built upon (μ-1,3-NO3) bridging coordination to two cis-(2,2′:6′,2′′-terpyridine)PdII units in a cofacial arrangement. The Pd atom is four-coordinated by a tridentate chelating 2,2′:6′,2′′-terpyridine ligand and one bridging nitrate ion, to form a distorted square-planar geometry. The two dimers aggregate alternately along a linear chain via Pd...Pd inter­actions [intra­dimer, 3.09 (1) Å; inter­dimer, 3.33 (1) Å]. The dimer-to-dimer aggregates arrange in a zigzag orientation along the b axis through π–π inter­actions [centroid–centroid distances 3.521 (6)–3.894 (6)Å] between terpyridine ligands and weak inter­molecular hydrogen bonds involving hexa­fluorido­phosphate anions (C—H...F) and the solvent acetonitrile mol­ecule (C—H...N).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042766/dn3057sup1.cif
Contains datablocks a, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042766/dn3057Isup2.hkl
Contains datablock I

CCDC reference: 663584

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.063
  • wR factor = 0.156
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O4 - N11 .. 7.02 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - N4 .. 6.18 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N11 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P2 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P4 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P6 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P7 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C61 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.33 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.25 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12 PLAT431_ALERT_2_C Short Inter HL..A Contact F22 .. O5 .. 2.98 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact F45 .. C33 .. 2.96 Ang.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C62 H47 F36 N15 O6 P6 Pd4 Atom count from _chemical_formula_moiety:C1802 H1323 N421 O180 Pd120 PLAT794_ALERT_5_G Check Predicted Bond Valency for Pd1 (2) 2.36 PLAT794_ALERT_5_G Check Predicted Bond Valency for Pd2 (2) 2.43 PLAT794_ALERT_5_G Check Predicted Bond Valency for Pd3 (2) 2.39 PLAT794_ALERT_5_G Check Predicted Bond Valency for Pd4 (2) 2.42
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion 4 ALERT type 5 Informative message, check

Comment top

Recently, we have been interested in using 2,2':6',2''-terpyridine palladium (II) nitrate as a coordinative array in molecular self-assembly(Huang & Ma, 2007). To our knowledge, its solid structure is usually proposed as a monomer, and the crystal structure of its hexafluorophosphate has been reported (Mei & Huang, 2007). Herein we report the synthesis and structure of {cis-[(2,2':6',2''-terpyridine)palladium(II)]2(µ-1,3-NO3)}3+ (I). X-ray crystallographic analysis reveals that the dimerized cis-(2,2':6',2''-terpyridine)Pd(II) units aggregate into a dimer-to-dimer linear conformation through direct metal-metal interaction and π-π stacking between terpyridine ligands. A similar structure of {cis-[(2,2'-bipyridine)palladium(II)]2(µ-1,3-NO3)2}2+ has been reported (Yu et al., 2001).

In each dimeric cation of the title compound, {cis-[(2,2':6',2''-terpyridine)palladium (II)]2}(µ-1,3-NO3)}3+, both Pd(II) atoms are coordinated by a 2,2':6',2''-terpyridine and bridged by nitrate anion in a cofacial arrangement. The geometry around Pd(II) is a distorted square-planar coordination, composed of three nitrogen atoms from the 2,2':6',2''-terpyridine and one oxygen atom from bridging nitrate (Fig. 1). The two bridged coordinated squares are arranged in an offset face-to-face stacking mode by a dihedral angle of 20°, conforming to an approximate π-π interaction. The resulting Pd···Pd distances (Pd1···Pd2 = 3.0939 (8) Å, Pd3···Pd4 = 3.0867 (8) Å) are significantly shorter than that in the 3,5-diphenyl pyrazolate bridged 2,2':6',2''-terpyridine palladinum complex [Pd2C45H33N8](NO3)3 (3.459 (1) Å)(Huang & Ma, 2007). The (µ-1,3-NO3) nitrato-bridged N—O bonds are significantly shorter [1.27 (1)–1.32 (1) Å] than those of the uncoordination [1.51 (1)–1.52 (1) Å].

Interestingly, the two dimers aggregate alternatively along the linear chain consisting of the four Pd(II) atoms with Pd···Pd distances of 3.09 (1) Å (intradimer) and 3.33 (1)Å (interdimer), showing quite strong metal-metal interactions. The dimer-to-dimer aggregates arrange in a zigzag orientation along crystal axis b through π-π interactions and short contacts involving hexafluorophosphate anions (C—H···F) and the solvent acetonitrile molecule (C—H···N). The centroid-centroid contact between two pyridine rings of the terpyridine molecules and the angle between the ring-centroid vector and the ring normal to one of the pyridine planes in dimeric cation include: Cg1 (N1, C1 to C5)···Cg4 (N5, C16 to C20) 3.521 (6) Å, 15.0 (9)°; Cg2(N2, C6 to C10) ···Cg5(N5, C21 to C25) 3.894 (6) Å, 16.6 (1)°; Cg3(N3, C11 to C15)···Cg6(N7, C26 to C30) 3.624 (6) Å, 17.4 (1)°; Cg7(N8, C31 to C35)···Cg10(N12, C46 to C50) 3.521 (6) Å, 16.0 (4)°; Cg8(N9, C36 to C40)···Cg11(N13, C51 to C55) 3.894 (6) Å, 18.4 (6)°; Cg9(N10, C41 to C45)···Cg12(N14, C56 to C60) 3.624 (6) Å, 21.0 (2)°. While the centroid-centroid contact between two pyridine rings of the terpyridine molecules between the dimeric cations is Cg4···Cg10 3.732 (6) Å, and the angle between the ring-centroid vector and the ring normal to one of the pyridine planes 20.5 (3)°.

Among six hexafluorophosphate anions, two lie on inversion centre (P6, 1/2, 0, 0; P7, 1, 0, 0). The weak non-classical hydrogen bonds that connect cationic dimers, anions and acetonitrile solvent are detailed in Table 1.

Related literature top

For related literature, see: Huang & Ma (2007); Mei & Huang (2007); Yu et al. (2001).

Experimental top

(2,2':6',2''-terpyridyl-κ3N)dinitratopalladium (46.4 mg, 0.10 mmol) was dissolved in water (5 ml), and a twofold excess of potassium hexafluorophosphate was added, which resulted in the immediate deposition deep yellow microcrystals. The crystals were filtered, washed with a minimum amount of cold water and dried under vacuum (quantative yield, of 58.3 mg). Crystals were obtained by the vapor diffusion of diethyl ether into a 2 mM solution of in acetonitrile. 1H NMR (400 MHz, [D3] acetonitrile): δ 7.55 (2H, m, Ph—H), 8.03 (4H, m, Ph—H), 8.18 (6H, m, Ph—H), 8.37 (2H, m, Ph—H) p.p.m.

Refinement top

All H atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.96 Å (methyl) with Uiso(H) = 1.2Ueq(aromatic) or Uiso(H) = 1.5Ueq(methyl).

Some residual electron density were difficult to modelize and therefore, the SQUEEZE function of PLATON (Spek, 2003) was used to eliminate the contribution of the electron density in the solvent region from the intensity data, and the solvent-free model was employed for the final refinement.

There are two voids of about 15 Å3 per unitl cell. PLATON estimated that each void contains 4.5 electrons which may correspond to roughly one water molecules within the cell.

Structure description top

Recently, we have been interested in using 2,2':6',2''-terpyridine palladium (II) nitrate as a coordinative array in molecular self-assembly(Huang & Ma, 2007). To our knowledge, its solid structure is usually proposed as a monomer, and the crystal structure of its hexafluorophosphate has been reported (Mei & Huang, 2007). Herein we report the synthesis and structure of {cis-[(2,2':6',2''-terpyridine)palladium(II)]2(µ-1,3-NO3)}3+ (I). X-ray crystallographic analysis reveals that the dimerized cis-(2,2':6',2''-terpyridine)Pd(II) units aggregate into a dimer-to-dimer linear conformation through direct metal-metal interaction and π-π stacking between terpyridine ligands. A similar structure of {cis-[(2,2'-bipyridine)palladium(II)]2(µ-1,3-NO3)2}2+ has been reported (Yu et al., 2001).

In each dimeric cation of the title compound, {cis-[(2,2':6',2''-terpyridine)palladium (II)]2}(µ-1,3-NO3)}3+, both Pd(II) atoms are coordinated by a 2,2':6',2''-terpyridine and bridged by nitrate anion in a cofacial arrangement. The geometry around Pd(II) is a distorted square-planar coordination, composed of three nitrogen atoms from the 2,2':6',2''-terpyridine and one oxygen atom from bridging nitrate (Fig. 1). The two bridged coordinated squares are arranged in an offset face-to-face stacking mode by a dihedral angle of 20°, conforming to an approximate π-π interaction. The resulting Pd···Pd distances (Pd1···Pd2 = 3.0939 (8) Å, Pd3···Pd4 = 3.0867 (8) Å) are significantly shorter than that in the 3,5-diphenyl pyrazolate bridged 2,2':6',2''-terpyridine palladinum complex [Pd2C45H33N8](NO3)3 (3.459 (1) Å)(Huang & Ma, 2007). The (µ-1,3-NO3) nitrato-bridged N—O bonds are significantly shorter [1.27 (1)–1.32 (1) Å] than those of the uncoordination [1.51 (1)–1.52 (1) Å].

Interestingly, the two dimers aggregate alternatively along the linear chain consisting of the four Pd(II) atoms with Pd···Pd distances of 3.09 (1) Å (intradimer) and 3.33 (1)Å (interdimer), showing quite strong metal-metal interactions. The dimer-to-dimer aggregates arrange in a zigzag orientation along crystal axis b through π-π interactions and short contacts involving hexafluorophosphate anions (C—H···F) and the solvent acetonitrile molecule (C—H···N). The centroid-centroid contact between two pyridine rings of the terpyridine molecules and the angle between the ring-centroid vector and the ring normal to one of the pyridine planes in dimeric cation include: Cg1 (N1, C1 to C5)···Cg4 (N5, C16 to C20) 3.521 (6) Å, 15.0 (9)°; Cg2(N2, C6 to C10) ···Cg5(N5, C21 to C25) 3.894 (6) Å, 16.6 (1)°; Cg3(N3, C11 to C15)···Cg6(N7, C26 to C30) 3.624 (6) Å, 17.4 (1)°; Cg7(N8, C31 to C35)···Cg10(N12, C46 to C50) 3.521 (6) Å, 16.0 (4)°; Cg8(N9, C36 to C40)···Cg11(N13, C51 to C55) 3.894 (6) Å, 18.4 (6)°; Cg9(N10, C41 to C45)···Cg12(N14, C56 to C60) 3.624 (6) Å, 21.0 (2)°. While the centroid-centroid contact between two pyridine rings of the terpyridine molecules between the dimeric cations is Cg4···Cg10 3.732 (6) Å, and the angle between the ring-centroid vector and the ring normal to one of the pyridine planes 20.5 (3)°.

Among six hexafluorophosphate anions, two lie on inversion centre (P6, 1/2, 0, 0; P7, 1, 0, 0). The weak non-classical hydrogen bonds that connect cationic dimers, anions and acetonitrile solvent are detailed in Table 1.

For related literature, see: Huang & Ma (2007); Mei & Huang (2007); Yu et al. (2001).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: RAPID-AUTO (Rigaku, 1999); data reduction: RAPID-AUTO (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top
[Figure 1] Fig. 1. The structures of independent cations title complexes, showing 30% probability displacement ellipsoids and the atom numbering scheme. H atoms have been omitted for clarity.The intermolecular Pd—Pd interaction is shown as dashed line.
µ-nitrato-bis[(2,2':6',2''-terpyridyl-κ3 N)palladium(II)] hexakis(hexafluorophosphate) acetonitrile solvate top
Crystal data top
[Pd2(C15H11N3)2NO3]PF6·C2H3NZ = 2
Mr = 2393.57F(000) = 2340
Triclinic, P1Dx = 1.965 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 14.0633 (3) ÅCell parameters from 683 reflections
b = 14.7277 (4) Åθ = 1.0–27.5°
c = 20.7043 (7) ŵ = 1.14 mm1
α = 104.681 (4)°T = 291 K
β = 90.450 (1)°Block, yellow
γ = 102.226 (3)°0.32 × 0.28 × 0.25 mm
V = 4045.6 (2) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
17102 independent reflections
Radiation source: Rotating Anode13353 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Oscillation scansθmax = 27.0°, θmin = 1.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1717
Tmin = 0.71, Tmax = 0.76k = 1818
27513 measured reflectionsl = 026
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0584P)2 + 15.4804P]
where P = (Fo2 + 2Fc2)/3
17102 reflections(Δ/σ)max = 0.001
1165 parametersΔρmax = 0.97 e Å3
0 restraintsΔρmin = 0.61 e Å3
Crystal data top
[Pd2(C15H11N3)2NO3]PF6·C2H3Nγ = 102.226 (3)°
Mr = 2393.57V = 4045.6 (2) Å3
Triclinic, P1Z = 2
a = 14.0633 (3) ÅMo Kα radiation
b = 14.7277 (4) ŵ = 1.14 mm1
c = 20.7043 (7) ÅT = 291 K
α = 104.681 (4)°0.32 × 0.28 × 0.25 mm
β = 90.450 (1)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
17102 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
13353 reflections with I > 2σ(I)
Tmin = 0.71, Tmax = 0.76Rint = 0.042
27513 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0584P)2 + 15.4804P]
where P = (Fo2 + 2Fc2)/3
17102 reflectionsΔρmax = 0.97 e Å3
1165 parametersΔρmin = 0.61 e Å3
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
xyzUiso*/Ueq
C10.8441 (6)0.2275 (5)0.1255 (4)0.0623 (18)
H10.80760.23490.09020.075*
C20.9424 (7)0.2307 (6)0.1205 (5)0.082 (3)
H20.97130.24000.08180.099*
C30.9971 (7)0.2206 (6)0.1706 (6)0.086 (3)
H31.06390.22540.16740.103*
C40.9523 (5)0.2029 (6)0.2273 (5)0.070 (2)
H40.98840.19370.26200.084*
C50.8541 (5)0.1994 (5)0.2312 (4)0.0542 (16)
C60.7971 (5)0.1778 (4)0.2868 (3)0.0506 (15)
C70.8311 (6)0.1654 (6)0.3457 (4)0.070 (2)
H70.89740.17140.35460.085*
C80.7660 (7)0.1443 (7)0.3908 (5)0.085 (3)
H80.78870.13510.43040.101*
C90.6679 (7)0.1363 (6)0.3796 (4)0.074 (2)
H90.62440.12230.41120.089*
C100.6351 (5)0.1496 (5)0.3197 (3)0.0565 (16)
C110.5346 (5)0.1491 (5)0.2974 (3)0.0555 (16)
C120.4539 (6)0.1237 (7)0.3313 (5)0.080 (3)
H120.45980.10500.37060.096*
C130.3645 (6)0.1267 (7)0.3060 (5)0.085 (3)
H130.30930.11160.32900.102*
C140.3557 (6)0.1513 (7)0.2477 (5)0.082 (3)
H140.29480.15210.23030.099*
C150.4389 (5)0.1753 (6)0.2146 (4)0.0642 (19)
H150.43310.19200.17460.077*
C160.8965 (6)0.4625 (5)0.1568 (4)0.0606 (18)
H160.84950.45920.12390.073*
C170.9929 (7)0.4792 (6)0.1429 (5)0.074 (2)
H171.01090.48730.10120.089*
C181.0616 (7)0.4837 (6)0.1907 (6)0.086 (3)
H181.12720.49500.18180.103*
C191.0344 (6)0.4714 (6)0.2529 (5)0.071 (2)
H191.08090.47290.28560.085*
C200.9358 (5)0.4568 (5)0.2648 (4)0.0521 (15)
C210.8970 (5)0.4443 (4)0.3283 (3)0.0493 (14)
C220.9466 (5)0.4412 (6)0.3856 (4)0.0644 (19)
H221.01380.44700.38750.077*
C230.8935 (6)0.4293 (6)0.4391 (4)0.070 (2)
H230.92570.42730.47800.084*
C240.7940 (6)0.4202 (6)0.4373 (3)0.0649 (19)
H240.75930.41180.47420.078*
C250.7471 (5)0.4238 (4)0.3800 (3)0.0473 (14)
C260.6412 (5)0.4126 (5)0.3665 (3)0.0479 (14)
C270.5710 (6)0.4027 (6)0.4121 (4)0.0658 (19)
H270.58880.40280.45550.079*
C280.4757 (6)0.3927 (6)0.3930 (4)0.071 (2)
H280.42800.38440.42310.085*
C290.4499 (6)0.3949 (6)0.3298 (4)0.067 (2)
H290.38500.38970.31690.080*
C300.5220 (5)0.4051 (5)0.2854 (3)0.0530 (15)
H300.50480.40670.24230.064*
C310.8777 (6)0.9041 (6)0.3936 (4)0.070 (2)
H310.84450.88340.42770.084*
C320.9779 (8)0.9376 (7)0.4015 (6)0.098 (3)
H321.01180.93830.44040.117*
C331.0271 (7)0.9702 (7)0.3515 (8)0.108 (4)
H331.09430.99390.35670.130*
C340.9757 (6)0.9672 (6)0.2939 (6)0.090 (3)
H341.00800.98830.25950.108*
C350.8759 (5)0.9327 (5)0.2875 (4)0.065 (2)
C360.8132 (6)0.9311 (5)0.2302 (4)0.0627 (19)
C370.8396 (8)0.9490 (7)0.1688 (5)0.090 (3)
H370.90490.96500.16000.108*
C380.7674 (9)0.9425 (8)0.1219 (6)0.105 (4)
H380.78460.95590.08140.126*
C390.6713 (8)0.9172 (8)0.1328 (5)0.093 (3)
H390.62340.91230.10000.112*
C400.6459 (6)0.8988 (5)0.1937 (4)0.0621 (18)
C410.5476 (5)0.8686 (5)0.2152 (3)0.0544 (16)
C420.4628 (7)0.8680 (7)0.1818 (4)0.077 (2)
H420.46440.88510.14150.093*
C430.3746 (7)0.8415 (8)0.2090 (5)0.089 (3)
H430.31630.83940.18650.107*
C440.3740 (6)0.8187 (7)0.2683 (5)0.080 (2)
H440.31540.80230.28750.096*
C450.4602 (5)0.8201 (6)0.2998 (4)0.0640 (19)
H450.45870.80320.34020.077*
C460.9099 (6)0.6866 (5)0.3674 (4)0.0586 (17)
H460.86500.67230.39820.070*
C471.0085 (6)0.7062 (6)0.3856 (4)0.072 (2)
H471.02930.70500.42810.086*
C481.0740 (6)0.7271 (6)0.3415 (5)0.079 (2)
H481.14030.74140.35380.095*
C491.0431 (5)0.7274 (6)0.2777 (4)0.068 (2)
H491.08810.74110.24700.081*
C500.9434 (5)0.7066 (5)0.2606 (3)0.0497 (14)
C510.8998 (4)0.7011 (5)0.1951 (3)0.0501 (15)
C520.9464 (6)0.7191 (7)0.1401 (4)0.072 (2)
H521.01390.73900.14220.086*
C530.8923 (6)0.7073 (8)0.0823 (4)0.086 (3)
H530.92360.71750.04450.104*
C540.7925 (6)0.6806 (7)0.0790 (4)0.077 (2)
H540.75620.67290.03950.093*
C550.7468 (5)0.6652 (5)0.1354 (3)0.0507 (15)
C560.6402 (5)0.6389 (5)0.1440 (3)0.0515 (15)
C570.5688 (5)0.6230 (6)0.0938 (4)0.0642 (19)
H570.58490.62830.05120.077*
C580.4731 (6)0.5989 (6)0.1088 (4)0.074 (2)
H580.42350.58730.07580.089*
C590.4500 (5)0.5917 (6)0.1722 (4)0.066 (2)
H590.38550.57520.18260.080*
C600.5254 (5)0.6098 (5)0.2195 (3)0.0538 (15)
H600.51060.60540.26250.065*
C610.1844 (10)0.9551 (11)0.1525 (7)0.131 (5)
C620.2378 (10)0.9738 (11)0.0963 (7)0.136 (5)
H62A0.30150.96070.09930.205*
H62B0.24401.04000.09640.205*
H62C0.20310.93320.05550.205*
F110.3301 (4)0.3848 (5)0.0682 (3)0.119 (2)
F120.2561 (7)0.3968 (8)0.1639 (5)0.197 (5)
F130.2405 (5)0.2426 (7)0.1524 (5)0.166 (4)
F140.3120 (8)0.2367 (7)0.0574 (6)0.206 (5)
F150.3859 (4)0.3387 (6)0.1503 (3)0.130 (3)
F160.1809 (4)0.2967 (6)0.0747 (3)0.129 (3)
F210.5986 (6)0.0326 (7)0.5747 (4)0.149 (3)
F220.6604 (6)0.0001 (4)0.4719 (3)0.113 (2)
F230.8034 (6)0.0203 (9)0.5206 (4)0.184 (4)
F240.7447 (6)0.0528 (5)0.6218 (3)0.123 (2)
F250.7226 (8)0.1334 (5)0.5479 (4)0.168 (4)
F260.6799 (8)0.0800 (5)0.5458 (3)0.162 (4)
F310.8351 (6)0.3205 (10)0.1226 (4)0.206 (5)
F320.7038 (5)0.2858 (8)0.0701 (4)0.183 (5)
F330.7890 (5)0.3505 (8)0.0223 (3)0.174 (4)
F340.9127 (5)0.4075 (7)0.0323 (4)0.157 (3)
F350.7673 (8)0.4243 (8)0.0488 (11)0.304 (10)
F360.8546 (11)0.2592 (9)0.0474 (9)0.269 (8)
F410.8457 (6)0.7797 (6)0.5182 (4)0.152 (3)
F420.7670 (5)0.7115 (9)0.5912 (4)0.184 (4)
F430.8981 (8)0.6827 (8)0.6252 (5)0.186 (4)
F440.9753 (6)0.7548 (13)0.5545 (6)0.264 (8)
F450.8903 (11)0.8221 (6)0.6293 (5)0.236 (6)
F460.8550 (13)0.6419 (6)0.5186 (5)0.249 (7)
F510.4019 (4)0.6030 (6)0.3473 (4)0.138 (3)
F520.3325 (4)0.5410 (5)0.4247 (3)0.0992 (18)
F530.1941 (4)0.5869 (6)0.4045 (3)0.116 (2)
F540.2658 (6)0.6500 (8)0.3285 (5)0.199 (5)
F550.2626 (6)0.4985 (7)0.3237 (4)0.153 (3)
F560.3341 (7)0.6859 (6)0.4324 (7)0.214 (5)
F610.4833 (6)0.0345 (5)0.0762 (3)0.127 (2)
F620.5061 (7)0.1027 (4)0.0091 (4)0.152 (3)
F630.6111 (4)0.0318 (6)0.0229 (4)0.131 (2)
F710.9031 (6)0.0317 (7)0.0224 (5)0.164 (3)
F721.0373 (8)0.0383 (8)0.0745 (4)0.191 (4)
F731.0362 (9)0.0982 (6)0.0120 (6)0.227 (6)
N10.8006 (4)0.2138 (4)0.1805 (3)0.0507 (12)
N20.7009 (4)0.1692 (4)0.2757 (3)0.0467 (12)
N30.5274 (4)0.1751 (4)0.2388 (3)0.0526 (13)
N40.6167 (4)0.3392 (5)0.1162 (3)0.0549 (14)
N50.8685 (4)0.4510 (4)0.2155 (3)0.0503 (12)
N60.7995 (3)0.4362 (3)0.3279 (2)0.0421 (11)
N70.6158 (4)0.4128 (4)0.3030 (2)0.0439 (11)
N80.8280 (4)0.9010 (4)0.3372 (3)0.0567 (14)
N90.7176 (4)0.9067 (4)0.2396 (3)0.0517 (13)
N100.5470 (4)0.8447 (4)0.2750 (3)0.0511 (12)
N110.6422 (4)0.7095 (5)0.3970 (3)0.0651 (16)
N120.8774 (4)0.6877 (4)0.3066 (3)0.0492 (12)
N130.8014 (4)0.6745 (4)0.1907 (2)0.0434 (11)
N140.6179 (4)0.6333 (4)0.2066 (2)0.0455 (11)
N150.1438 (11)0.9385 (13)0.1956 (7)0.198 (7)
O10.6131 (4)0.2523 (4)0.1226 (3)0.0703 (14)
O20.5685 (5)0.3518 (6)0.0542 (3)0.105 (2)
O30.6582 (3)0.4170 (3)0.1593 (2)0.0505 (10)
O40.6716 (4)0.6451 (3)0.3534 (2)0.0551 (11)
O50.6432 (4)0.7971 (4)0.3917 (3)0.0757 (15)
O60.6025 (6)0.6805 (6)0.4584 (3)0.117 (3)
P10.28359 (14)0.31449 (18)0.11135 (11)0.0682 (5)
P20.70198 (19)0.02723 (16)0.54697 (10)0.0701 (6)
P30.80942 (15)0.3441 (2)0.05047 (11)0.0729 (6)
P40.87092 (17)0.73181 (17)0.57193 (12)0.0735 (6)
P50.29837 (15)0.59521 (18)0.37584 (12)0.0693 (6)
P60.50000.00000.00000.0582 (6)
P71.00000.00000.00000.0977 (13)
Pd10.65777 (4)0.20609 (3)0.19879 (2)0.04358 (12)
Pd20.73012 (3)0.42735 (3)0.24547 (2)0.03875 (11)
Pd30.68166 (4)0.85813 (3)0.31629 (2)0.04592 (12)
Pd40.73706 (3)0.66080 (3)0.27017 (2)0.04043 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.075 (5)0.055 (4)0.058 (4)0.016 (3)0.021 (4)0.015 (3)
C20.094 (7)0.069 (5)0.092 (6)0.027 (5)0.048 (6)0.025 (5)
C30.065 (5)0.069 (5)0.123 (8)0.016 (4)0.030 (6)0.020 (5)
C40.051 (4)0.065 (5)0.093 (6)0.013 (3)0.006 (4)0.022 (4)
C50.059 (4)0.042 (3)0.062 (4)0.010 (3)0.004 (3)0.014 (3)
C60.052 (4)0.043 (3)0.059 (4)0.009 (3)0.003 (3)0.019 (3)
C70.064 (5)0.077 (5)0.079 (5)0.013 (4)0.011 (4)0.040 (4)
C80.091 (7)0.101 (7)0.072 (5)0.019 (5)0.012 (5)0.043 (5)
C90.084 (6)0.084 (6)0.066 (5)0.014 (4)0.013 (4)0.046 (4)
C100.066 (4)0.056 (4)0.056 (4)0.012 (3)0.009 (3)0.030 (3)
C110.057 (4)0.055 (4)0.057 (4)0.006 (3)0.005 (3)0.024 (3)
C120.069 (5)0.102 (7)0.086 (6)0.017 (5)0.026 (5)0.057 (5)
C130.061 (5)0.094 (7)0.111 (7)0.011 (4)0.024 (5)0.051 (6)
C140.049 (4)0.093 (6)0.111 (7)0.010 (4)0.000 (5)0.043 (6)
C150.058 (4)0.066 (5)0.072 (5)0.008 (3)0.004 (4)0.029 (4)
C160.069 (5)0.057 (4)0.051 (4)0.006 (3)0.016 (3)0.011 (3)
C170.073 (5)0.065 (5)0.080 (5)0.008 (4)0.037 (5)0.017 (4)
C180.055 (5)0.070 (5)0.124 (8)0.009 (4)0.038 (5)0.012 (5)
C190.049 (4)0.066 (5)0.088 (6)0.012 (3)0.010 (4)0.005 (4)
C200.038 (3)0.048 (4)0.064 (4)0.005 (3)0.006 (3)0.006 (3)
C210.050 (4)0.037 (3)0.054 (4)0.006 (3)0.007 (3)0.002 (3)
C220.047 (4)0.068 (5)0.074 (5)0.011 (3)0.013 (4)0.013 (4)
C230.067 (5)0.089 (6)0.053 (4)0.020 (4)0.016 (4)0.018 (4)
C240.076 (5)0.078 (5)0.036 (3)0.012 (4)0.007 (3)0.012 (3)
C250.057 (4)0.045 (3)0.037 (3)0.010 (3)0.003 (3)0.009 (2)
C260.052 (4)0.052 (4)0.043 (3)0.018 (3)0.009 (3)0.014 (3)
C270.067 (5)0.086 (5)0.051 (4)0.021 (4)0.017 (4)0.026 (4)
C280.062 (5)0.091 (6)0.073 (5)0.028 (4)0.032 (4)0.036 (4)
C290.049 (4)0.080 (5)0.078 (5)0.024 (4)0.011 (4)0.025 (4)
C300.044 (3)0.064 (4)0.056 (4)0.016 (3)0.004 (3)0.022 (3)
C310.070 (5)0.061 (5)0.067 (5)0.020 (4)0.017 (4)0.010 (4)
C320.077 (7)0.075 (6)0.121 (9)0.024 (5)0.025 (6)0.016 (6)
C330.054 (6)0.072 (6)0.184 (13)0.013 (5)0.007 (7)0.009 (7)
C340.053 (5)0.058 (5)0.153 (10)0.007 (4)0.020 (6)0.020 (5)
C350.053 (4)0.042 (4)0.095 (6)0.009 (3)0.017 (4)0.011 (4)
C360.062 (4)0.045 (4)0.085 (5)0.012 (3)0.030 (4)0.023 (4)
C370.090 (7)0.089 (6)0.106 (7)0.021 (5)0.055 (6)0.052 (6)
C380.119 (9)0.124 (9)0.096 (7)0.031 (7)0.049 (7)0.069 (7)
C390.110 (8)0.118 (8)0.081 (6)0.041 (6)0.034 (6)0.064 (6)
C400.068 (5)0.059 (4)0.065 (4)0.013 (3)0.014 (4)0.028 (4)
C410.054 (4)0.063 (4)0.047 (3)0.011 (3)0.004 (3)0.016 (3)
C420.077 (6)0.094 (6)0.068 (5)0.027 (5)0.005 (4)0.027 (5)
C430.057 (5)0.110 (8)0.095 (7)0.022 (5)0.004 (5)0.015 (6)
C440.055 (5)0.099 (7)0.082 (6)0.015 (4)0.016 (4)0.018 (5)
C450.055 (4)0.074 (5)0.064 (4)0.015 (4)0.016 (4)0.019 (4)
C460.066 (4)0.056 (4)0.052 (4)0.012 (3)0.005 (3)0.013 (3)
C470.071 (5)0.067 (5)0.074 (5)0.023 (4)0.023 (4)0.004 (4)
C480.054 (5)0.071 (5)0.104 (7)0.012 (4)0.019 (5)0.013 (5)
C490.046 (4)0.064 (5)0.089 (6)0.020 (3)0.003 (4)0.007 (4)
C500.043 (3)0.055 (4)0.051 (3)0.014 (3)0.005 (3)0.010 (3)
C510.039 (3)0.060 (4)0.053 (4)0.017 (3)0.009 (3)0.011 (3)
C520.045 (4)0.108 (7)0.066 (5)0.020 (4)0.024 (4)0.026 (4)
C530.064 (5)0.142 (9)0.059 (5)0.028 (5)0.027 (4)0.031 (5)
C540.073 (5)0.114 (7)0.046 (4)0.018 (5)0.007 (4)0.024 (4)
C550.047 (4)0.066 (4)0.041 (3)0.017 (3)0.004 (3)0.014 (3)
C560.055 (4)0.058 (4)0.045 (3)0.017 (3)0.003 (3)0.017 (3)
C570.058 (4)0.085 (5)0.051 (4)0.012 (4)0.011 (3)0.024 (4)
C580.060 (5)0.090 (6)0.071 (5)0.008 (4)0.019 (4)0.026 (4)
C590.035 (3)0.076 (5)0.086 (5)0.000 (3)0.004 (3)0.028 (4)
C600.047 (4)0.058 (4)0.054 (4)0.004 (3)0.003 (3)0.018 (3)
C610.092 (8)0.149 (12)0.122 (10)0.004 (8)0.036 (8)0.001 (9)
C620.109 (10)0.170 (13)0.129 (11)0.013 (9)0.039 (8)0.051 (10)
F110.087 (4)0.168 (6)0.110 (4)0.013 (4)0.021 (3)0.082 (4)
F120.151 (7)0.239 (11)0.175 (8)0.095 (7)0.030 (6)0.041 (8)
F130.095 (5)0.240 (10)0.210 (8)0.005 (5)0.006 (5)0.177 (8)
F140.203 (10)0.135 (7)0.239 (11)0.043 (7)0.072 (8)0.034 (7)
F150.060 (3)0.229 (8)0.119 (5)0.012 (4)0.020 (3)0.096 (5)
F160.061 (3)0.208 (7)0.125 (5)0.007 (4)0.022 (3)0.085 (5)
F210.114 (5)0.202 (8)0.134 (6)0.056 (5)0.020 (5)0.030 (6)
F220.193 (7)0.080 (4)0.064 (3)0.027 (4)0.021 (4)0.020 (3)
F230.127 (6)0.325 (14)0.115 (6)0.103 (8)0.037 (5)0.038 (7)
F240.164 (6)0.146 (6)0.060 (3)0.055 (5)0.002 (4)0.012 (3)
F250.309 (12)0.070 (4)0.111 (5)0.019 (5)0.005 (6)0.017 (4)
F260.319 (12)0.077 (4)0.097 (5)0.043 (6)0.030 (6)0.035 (4)
F310.094 (5)0.412 (17)0.085 (5)0.040 (7)0.032 (4)0.025 (7)
F320.071 (4)0.304 (12)0.100 (5)0.024 (5)0.020 (4)0.024 (6)
F330.095 (5)0.335 (13)0.077 (4)0.001 (6)0.004 (4)0.066 (6)
F340.085 (4)0.204 (8)0.139 (6)0.046 (5)0.015 (4)0.028 (6)
F350.159 (9)0.164 (10)0.64 (3)0.063 (8)0.002 (14)0.174 (15)
F360.276 (15)0.214 (12)0.41 (2)0.133 (11)0.162 (15)0.183 (13)
F410.176 (7)0.186 (8)0.151 (6)0.087 (6)0.032 (6)0.107 (6)
F420.084 (5)0.335 (14)0.149 (7)0.035 (6)0.004 (5)0.105 (8)
F430.229 (10)0.249 (11)0.158 (7)0.156 (9)0.021 (7)0.105 (8)
F440.078 (5)0.54 (3)0.200 (10)0.030 (9)0.008 (6)0.174 (14)
F450.407 (19)0.097 (6)0.153 (8)0.014 (8)0.026 (10)0.004 (6)
F460.47 (2)0.097 (6)0.157 (8)0.072 (9)0.027 (11)0.012 (6)
F510.073 (4)0.206 (8)0.187 (7)0.053 (4)0.067 (4)0.124 (6)
F520.096 (4)0.155 (5)0.074 (3)0.061 (4)0.017 (3)0.052 (3)
F530.070 (3)0.205 (7)0.106 (4)0.060 (4)0.032 (3)0.076 (5)
F540.160 (7)0.317 (12)0.263 (11)0.158 (8)0.121 (7)0.245 (10)
F550.125 (6)0.196 (8)0.105 (5)0.051 (5)0.030 (4)0.029 (5)
F560.175 (9)0.090 (5)0.321 (14)0.025 (5)0.007 (9)0.043 (7)
F610.162 (6)0.137 (6)0.062 (3)0.017 (5)0.024 (4)0.006 (3)
F620.258 (10)0.057 (3)0.126 (5)0.006 (4)0.064 (6)0.024 (3)
F630.076 (4)0.180 (7)0.135 (6)0.010 (4)0.008 (4)0.052 (5)
F710.125 (6)0.173 (8)0.188 (8)0.049 (5)0.075 (6)0.021 (6)
F720.230 (11)0.221 (11)0.119 (6)0.103 (9)0.015 (7)0.007 (7)
F730.296 (14)0.102 (6)0.278 (13)0.015 (7)0.149 (11)0.063 (7)
N10.053 (3)0.045 (3)0.055 (3)0.010 (2)0.011 (3)0.013 (2)
N20.051 (3)0.046 (3)0.049 (3)0.012 (2)0.003 (2)0.024 (2)
N30.049 (3)0.061 (3)0.054 (3)0.012 (2)0.005 (2)0.026 (3)
N40.054 (3)0.073 (4)0.046 (3)0.022 (3)0.012 (3)0.023 (3)
N50.048 (3)0.049 (3)0.048 (3)0.003 (2)0.009 (2)0.007 (2)
N60.040 (3)0.044 (3)0.038 (2)0.007 (2)0.003 (2)0.006 (2)
N70.041 (3)0.051 (3)0.042 (3)0.015 (2)0.006 (2)0.012 (2)
N80.050 (3)0.044 (3)0.069 (4)0.010 (2)0.001 (3)0.003 (3)
N90.052 (3)0.046 (3)0.061 (3)0.010 (2)0.018 (3)0.022 (3)
N100.050 (3)0.054 (3)0.051 (3)0.013 (2)0.010 (2)0.016 (2)
N110.055 (4)0.087 (5)0.052 (3)0.004 (3)0.002 (3)0.025 (3)
N120.049 (3)0.043 (3)0.050 (3)0.011 (2)0.006 (2)0.001 (2)
N130.040 (3)0.051 (3)0.038 (2)0.011 (2)0.008 (2)0.010 (2)
N140.044 (3)0.049 (3)0.043 (3)0.009 (2)0.003 (2)0.012 (2)
N150.155 (12)0.246 (18)0.142 (11)0.010 (11)0.075 (10)0.001 (11)
O10.087 (4)0.066 (3)0.057 (3)0.011 (3)0.006 (3)0.021 (3)
O20.099 (5)0.152 (7)0.079 (4)0.038 (5)0.006 (4)0.050 (4)
O30.063 (3)0.047 (2)0.041 (2)0.010 (2)0.000 (2)0.0133 (19)
O40.064 (3)0.060 (3)0.043 (2)0.012 (2)0.015 (2)0.016 (2)
O50.091 (4)0.079 (4)0.058 (3)0.016 (3)0.014 (3)0.022 (3)
O60.113 (6)0.167 (8)0.074 (4)0.007 (5)0.021 (4)0.055 (5)
P10.0466 (10)0.0995 (16)0.0659 (12)0.0147 (10)0.0017 (9)0.0360 (12)
P20.0977 (16)0.0608 (12)0.0550 (11)0.0238 (11)0.0108 (11)0.0156 (9)
P30.0496 (11)0.1117 (18)0.0578 (11)0.0066 (11)0.0118 (9)0.0319 (12)
P40.0654 (13)0.0750 (14)0.0806 (14)0.0214 (10)0.0151 (11)0.0168 (11)
P50.0532 (11)0.0926 (16)0.0769 (13)0.0260 (10)0.0190 (10)0.0399 (12)
P60.0728 (17)0.0480 (14)0.0519 (14)0.0096 (12)0.0047 (12)0.0130 (11)
P70.096 (3)0.075 (2)0.107 (3)0.0043 (19)0.050 (2)0.008 (2)
Pd10.0495 (3)0.0423 (2)0.0410 (2)0.00723 (19)0.00250 (19)0.01685 (19)
Pd20.0396 (2)0.0424 (2)0.0338 (2)0.00792 (17)0.00260 (17)0.01008 (17)
Pd30.0478 (3)0.0451 (3)0.0434 (2)0.0076 (2)0.0087 (2)0.0111 (2)
Pd40.0399 (2)0.0444 (2)0.0359 (2)0.00804 (18)0.00250 (18)0.00956 (18)
Geometric parameters (Å, º) top
C1—N11.337 (9)C48—C491.389 (12)
C1—C21.379 (12)C48—H480.9300
C1—H10.9300C49—C501.392 (9)
C2—C31.343 (14)C49—H490.9300
C2—H20.9300C50—N121.373 (8)
C3—C41.392 (13)C50—C511.460 (9)
C3—H30.9300C51—N131.352 (8)
C4—C51.375 (10)C51—C521.374 (10)
C4—H40.9300C52—C531.366 (12)
C5—N11.372 (9)C52—H520.9300
C5—C61.470 (9)C53—C541.370 (12)
C6—N21.345 (8)C53—H530.9300
C6—C71.376 (10)C54—C551.383 (10)
C7—C81.358 (12)C54—H540.9300
C7—H70.9300C55—N131.335 (8)
C8—C91.373 (12)C55—C561.490 (9)
C8—H80.9300C56—N141.355 (8)
C9—C101.395 (10)C56—C571.380 (9)
C9—H90.9300C57—C581.376 (11)
C10—N21.341 (8)C57—H570.9300
C10—C111.482 (10)C58—C591.380 (11)
C11—N31.372 (8)C58—H580.9300
C11—C121.372 (10)C59—C601.373 (10)
C12—C131.373 (12)C59—H590.9300
C12—H120.9300C60—N141.321 (8)
C13—C141.356 (12)C60—H600.9300
C13—H130.9300C61—N151.115 (17)
C14—C151.387 (11)C61—C621.443 (17)
C14—H140.9300C62—H62A0.9602
C15—N31.338 (9)C62—H62B0.9597
C15—H150.9300C62—H62C0.9608
C16—N51.322 (8)F11—P11.579 (6)
C16—C171.372 (11)F12—P11.529 (8)
C16—H160.9300F13—P11.550 (6)
C17—C181.357 (13)F14—P11.508 (8)
C17—H170.9300F15—P11.570 (5)
C18—C191.392 (13)F16—P11.567 (6)
C18—H180.9300F21—P21.577 (8)
C19—C201.391 (10)F22—P21.577 (5)
C19—H190.9300F23—P21.546 (8)
C20—N51.361 (9)F24—P21.581 (6)
C20—C211.466 (10)F25—P21.524 (7)
C21—N61.351 (8)F26—P21.537 (7)
C21—C221.388 (10)F31—P31.511 (7)
C22—C231.369 (11)F32—P31.543 (7)
C22—H220.9300F33—P31.518 (7)
C23—C241.377 (11)F34—P31.536 (6)
C23—H230.9300F35—P31.421 (10)
C24—C251.371 (9)F36—P31.533 (11)
C24—H240.9300F41—P41.536 (7)
C25—N61.340 (8)F42—P41.507 (8)
C25—C261.480 (9)F43—P41.550 (7)
C26—N71.361 (8)F44—P41.503 (9)
C26—C271.382 (9)F45—P41.515 (9)
C27—C281.362 (11)F46—P41.468 (9)
C27—H270.9300F51—P51.568 (5)
C28—C291.364 (11)F52—P51.567 (5)
C28—H280.9300F53—P51.579 (5)
C29—C301.384 (10)F54—P51.541 (6)
C29—H290.9300F55—P51.535 (8)
C30—N71.340 (8)F56—P51.523 (9)
C30—H300.9300F61—P61.565 (5)
C31—N81.341 (10)F62—P61.556 (6)
C31—C321.384 (13)F63—P61.566 (6)
C31—H310.9300F71—P71.568 (7)
C32—C331.380 (16)F72—P71.547 (9)
C32—H320.9300F73—P71.511 (8)
C33—C341.376 (16)N1—Pd12.032 (5)
C33—H330.9300N2—Pd11.939 (5)
C34—C351.382 (11)N3—Pd12.029 (5)
C34—H340.9300N4—O31.282 (7)
C35—N81.362 (10)N4—O11.310 (7)
C35—C361.465 (12)N4—O21.518 (8)
C36—N91.344 (9)N5—Pd22.033 (5)
C36—C371.399 (11)N6—Pd21.920 (5)
C37—C381.371 (15)N7—Pd22.015 (5)
C37—H370.9300N8—Pd32.029 (6)
C38—C391.361 (14)N9—Pd31.930 (5)
C38—H380.9300N10—Pd32.022 (6)
C39—C401.390 (10)N11—O41.273 (8)
C39—H390.9300N11—O51.320 (8)
C40—N91.346 (9)N11—O61.515 (8)
C40—C411.468 (10)N12—Pd42.029 (5)
C41—N101.370 (8)N13—Pd41.919 (5)
C41—C421.371 (11)N14—Pd42.027 (5)
C42—C431.388 (13)O1—Pd12.014 (5)
C42—H420.9300O3—Pd21.999 (4)
C43—C441.353 (13)O4—Pd42.003 (4)
C43—H430.9300O5—Pd32.014 (5)
C44—C451.366 (11)P6—F62i1.556 (6)
C44—H440.9300P6—F61i1.565 (5)
C45—N101.343 (9)P6—F63i1.566 (6)
C45—H450.9300P7—F73ii1.511 (8)
C46—N121.343 (8)P7—F72ii1.547 (9)
C46—C471.383 (11)P7—F71ii1.568 (7)
C46—H460.9300Pd1—Pd23.0940 (6)
C47—C481.347 (13)Pd3—Pd43.0868 (7)
C47—H470.9300
N1—C1—C2120.6 (8)C5—N1—Pd1113.2 (4)
N1—C1—H1119.7C10—N2—C6123.4 (6)
C2—C1—H1119.7C10—N2—Pd1118.1 (4)
C3—C2—C1121.3 (8)C6—N2—Pd1117.8 (4)
C3—C2—H2119.4C15—N3—C11118.4 (6)
C1—C2—H2119.4C15—N3—Pd1128.5 (5)
C2—C3—C4118.9 (8)C11—N3—Pd1113.1 (4)
C2—C3—H3120.6O3—N4—O1124.7 (5)
C4—C3—H3120.6O3—N4—O2115.8 (6)
C5—C4—C3119.1 (8)O1—N4—O2119.5 (6)
C5—C4—H4120.5C16—N5—C20120.2 (6)
C3—C4—H4120.5C16—N5—Pd2127.5 (5)
N1—C5—C4120.8 (7)C20—N5—Pd2112.2 (4)
N1—C5—C6114.4 (6)C25—N6—C21123.4 (5)
C4—C5—C6124.7 (7)C25—N6—Pd2117.8 (4)
N2—C6—C7119.2 (7)C21—N6—Pd2118.4 (4)
N2—C6—C5113.2 (6)C30—N7—C26119.2 (5)
C7—C6—C5127.6 (7)C30—N7—Pd2127.3 (4)
C8—C7—C6118.7 (8)C26—N7—Pd2113.5 (4)
C8—C7—H7120.6C31—N8—C35119.9 (7)
C6—C7—H7120.6C31—N8—Pd3127.3 (6)
C7—C8—C9122.1 (8)C35—N8—Pd3112.7 (5)
C7—C8—H8119.0C36—N9—C40124.0 (6)
C9—C8—H8119.0C36—N9—Pd3117.6 (5)
C8—C9—C10118.2 (7)C40—N9—Pd3117.4 (4)
C8—C9—H9120.9C45—N10—C41117.7 (6)
C10—C9—H9120.9C45—N10—Pd3128.6 (5)
N2—C10—C9118.5 (7)C41—N10—Pd3113.6 (4)
N2—C10—C11113.0 (6)O4—N11—O5124.9 (6)
C9—C10—C11128.4 (7)O4—N11—O6116.0 (7)
N3—C11—C12121.7 (7)O5—N11—O6119.1 (7)
N3—C11—C10114.5 (6)C46—N12—C50119.3 (6)
C12—C11—C10123.8 (7)C46—N12—Pd4127.8 (5)
C11—C12—C13118.5 (8)C50—N12—Pd4112.9 (4)
C11—C12—H12120.8C55—N13—C51123.2 (5)
C13—C12—H12120.8C55—N13—Pd4118.5 (4)
C14—C13—C12120.7 (8)C51—N13—Pd4118.1 (4)
C14—C13—H13119.6C60—N14—C56119.1 (6)
C12—C13—H13119.6C60—N14—Pd4127.7 (4)
C13—C14—C15118.9 (8)C56—N14—Pd4113.2 (4)
C13—C14—H14120.6N4—O1—Pd1131.5 (4)
C15—C14—H14120.6N4—O3—Pd2126.5 (4)
N3—C15—C14121.8 (7)N11—O4—Pd4126.9 (4)
N3—C15—H15119.1N11—O5—Pd3130.4 (5)
C14—C15—H15119.1F14—P1—F12177.1 (7)
N5—C16—C17121.9 (8)F14—P1—F1392.4 (6)
N5—C16—H16119.1F12—P1—F1390.5 (6)
C17—C16—H16119.1F14—P1—F1691.5 (6)
C18—C17—C16119.2 (8)F12—P1—F1688.1 (5)
C18—C17—H17120.4F13—P1—F1689.8 (4)
C16—C17—H17120.4F14—P1—F1591.7 (6)
C17—C18—C19120.3 (8)F12—P1—F1588.6 (5)
C17—C18—H18119.9F13—P1—F1591.5 (4)
C19—C18—H18119.9F16—P1—F15176.5 (5)
C20—C19—C18118.1 (8)F14—P1—F1185.5 (6)
C20—C19—H19121.0F12—P1—F1191.7 (6)
C18—C19—H19121.0F13—P1—F11177.7 (5)
N5—C20—C19120.2 (7)F16—P1—F1191.2 (3)
N5—C20—C21115.8 (5)F15—P1—F1187.7 (3)
C19—C20—C21124.0 (7)F25—P2—F26179.3 (7)
N6—C21—C22119.0 (6)F25—P2—F2390.1 (6)
N6—C21—C20112.2 (6)F26—P2—F2390.5 (6)
C22—C21—C20128.9 (6)F25—P2—F2190.9 (5)
C23—C22—C21117.9 (7)F26—P2—F2188.5 (5)
C23—C22—H22121.1F23—P2—F21178.8 (6)
C21—C22—H22121.1F25—P2—F2289.7 (4)
C22—C23—C24122.1 (7)F26—P2—F2289.9 (4)
C22—C23—H23118.9F23—P2—F2288.1 (4)
C24—C23—H23118.9F21—P2—F2292.6 (4)
C25—C24—C23118.6 (7)F25—P2—F2491.2 (4)
C25—C24—H24120.7F26—P2—F2489.2 (4)
C23—C24—H24120.7F23—P2—F2491.2 (4)
N6—C25—C24119.1 (6)F21—P2—F2488.2 (4)
N6—C25—C26113.3 (5)F22—P2—F24178.8 (4)
C24—C25—C26127.6 (6)F35—P3—F3199.8 (10)
N7—C26—C27120.6 (6)F35—P3—F3390.8 (9)
N7—C26—C25113.9 (5)F31—P3—F33169.3 (7)
C27—C26—C25125.5 (6)F35—P3—F36176.4 (11)
C28—C27—C26119.5 (7)F31—P3—F3683.7 (7)
C28—C27—H27120.2F33—P3—F3685.7 (7)
C26—C27—H27120.2F35—P3—F3492.9 (7)
C27—C28—C29120.3 (7)F31—P3—F3488.1 (5)
C27—C28—H28119.9F33—P3—F3492.9 (4)
C29—C28—H28119.9F36—P3—F3486.6 (7)
C28—C29—C30118.7 (7)F35—P3—F3283.6 (7)
C28—C29—H29120.6F31—P3—F3291.2 (4)
C30—C29—H29120.6F33—P3—F3288.5 (4)
N7—C30—C29121.7 (6)F36—P3—F3296.9 (8)
N7—C30—H30119.2F34—P3—F32176.3 (6)
C29—C30—H30119.2F46—P4—F4489.1 (9)
N8—C31—C32120.8 (10)F46—P4—F4292.7 (8)
N8—C31—H31119.6F44—P4—F42178.2 (8)
C32—C31—H31119.6F46—P4—F45176.8 (8)
C33—C32—C31119.7 (11)F44—P4—F4590.1 (8)
C33—C32—H32120.1F42—P4—F4588.1 (7)
C31—C32—H32120.1F46—P4—F4186.8 (6)
C34—C33—C32119.3 (10)F44—P4—F4187.5 (6)
C34—C33—H33120.4F42—P4—F4192.7 (5)
C32—C33—H33120.4F45—P4—F4196.3 (6)
C33—C34—C35119.4 (10)F46—P4—F4392.5 (6)
C33—C34—H34120.3F44—P4—F4391.5 (6)
C35—C34—H34120.3F42—P4—F4388.3 (5)
N8—C35—C34120.8 (9)F45—P4—F4384.4 (6)
N8—C35—C36114.9 (6)F41—P4—F43178.8 (5)
C34—C35—C36124.2 (9)F56—P5—F55174.7 (6)
N9—C36—C37117.9 (8)F56—P5—F5493.8 (7)
N9—C36—C35113.0 (6)F55—P5—F5491.3 (6)
C37—C36—C35129.0 (8)F56—P5—F5285.4 (6)
C38—C37—C36118.8 (9)F55—P5—F5289.6 (4)
C38—C37—H37120.6F54—P5—F52179.1 (6)
C36—C37—H37120.6F56—P5—F5191.8 (6)
C39—C38—C37121.9 (9)F55—P5—F5189.5 (5)
C39—C38—H38119.1F54—P5—F5191.8 (4)
C37—C38—H38119.1F52—P5—F5188.0 (3)
C38—C39—C40118.8 (10)F56—P5—F5388.4 (5)
C38—C39—H39120.6F55—P5—F5390.4 (4)
C40—C39—H39120.6F54—P5—F5388.4 (3)
N9—C40—C39118.6 (8)F52—P5—F5391.9 (3)
N9—C40—C41113.7 (6)F51—P5—F53179.8 (4)
C39—C40—C41127.7 (8)F62—P6—F62i180.0 (8)
N10—C41—C42121.4 (7)F62—P6—F6191.6 (4)
N10—C41—C40113.7 (6)F62i—P6—F6188.4 (4)
C42—C41—C40124.9 (7)F62—P6—F61i88.4 (4)
C41—C42—C43119.1 (8)F62i—P6—F61i91.6 (4)
C41—C42—H42120.4F61—P6—F61i180.0 (6)
C43—C42—H42120.4F62—P6—F6388.0 (4)
C44—C43—C42119.5 (9)F62i—P6—F6392.0 (4)
C44—C43—H43120.2F61—P6—F6385.2 (4)
C42—C43—H43120.2F61i—P6—F6394.8 (4)
C43—C44—C45119.4 (8)F62—P6—F63i92.0 (4)
C43—C44—H44120.3F62i—P6—F63i88.0 (4)
C45—C44—H44120.3F61—P6—F63i94.8 (4)
N10—C45—C44122.8 (8)F61i—P6—F63i85.2 (4)
N10—C45—H45118.6F63—P6—F63i180.0 (6)
C44—C45—H45118.6F73ii—P7—F73180.0 (9)
N12—C46—C47121.7 (8)F73ii—P7—F7288.6 (7)
N12—C46—H46119.2F73—P7—F7291.4 (7)
C47—C46—H46119.2F73ii—P7—F72ii91.4 (7)
C48—C47—C46119.6 (8)F73—P7—F72ii88.6 (7)
C48—C47—H47120.2F72—P7—F72ii180.0 (10)
C46—C47—H47120.2F73ii—P7—F71ii87.9 (6)
C47—C48—C49120.4 (8)F73—P7—F71ii92.1 (6)
C47—C48—H48119.8F72—P7—F71ii93.3 (5)
C49—C48—H48119.8F72ii—P7—F71ii86.7 (5)
C48—C49—C50118.8 (8)F73ii—P7—F7192.1 (6)
C48—C49—H49120.6F73—P7—F7187.9 (6)
C50—C49—H49120.6F72—P7—F7186.7 (5)
N12—C50—C49120.2 (7)F72ii—P7—F7193.3 (5)
N12—C50—C51114.5 (5)F71ii—P7—F71180.0 (10)
C49—C50—C51125.3 (7)N2—Pd1—O1176.5 (2)
N13—C51—C52118.7 (6)N2—Pd1—N380.9 (2)
N13—C51—C50113.3 (5)O1—Pd1—N398.5 (2)
C52—C51—C50128.0 (6)N2—Pd1—N180.5 (2)
C53—C52—C51119.2 (7)O1—Pd1—N1100.3 (2)
C53—C52—H52120.4N3—Pd1—N1160.9 (2)
C51—C52—H52120.4N2—Pd1—Pd2100.70 (16)
C52—C53—C54121.0 (7)O1—Pd1—Pd276.11 (15)
C52—C53—H53119.5N3—Pd1—Pd2106.22 (17)
C54—C53—H53119.5N1—Pd1—Pd281.66 (15)
C53—C54—C55119.0 (8)N6—Pd2—O3179.5 (2)
C53—C54—H54120.5N6—Pd2—N781.2 (2)
C55—C54—H54120.5O3—Pd2—N798.98 (19)
N13—C55—C54118.8 (6)N6—Pd2—N581.1 (2)
N13—C55—C56112.9 (5)O3—Pd2—N598.8 (2)
C54—C55—C56128.2 (6)N7—Pd2—N5162.1 (2)
N14—C56—C57121.7 (6)N6—Pd2—Pd198.75 (15)
N14—C56—C55114.2 (5)O3—Pd2—Pd180.84 (12)
C57—C56—C55124.0 (6)N7—Pd2—Pd181.19 (15)
C58—C57—C56117.8 (7)N5—Pd2—Pd1103.92 (15)
C58—C57—H57121.1N9—Pd3—O5175.6 (2)
C56—C57—H57121.1N9—Pd3—N1080.8 (2)
C57—C58—C59120.7 (7)O5—Pd3—N1098.7 (2)
C57—C58—H58119.7N9—Pd3—N880.8 (3)
C59—C58—H58119.7O5—Pd3—N8100.0 (3)
C60—C59—C58117.8 (7)N10—Pd3—N8160.8 (2)
C60—C59—H59121.1N9—Pd3—Pd499.25 (16)
C58—C59—H59121.1O5—Pd3—Pd476.68 (17)
N14—C60—C59122.8 (7)N10—Pd3—Pd4107.76 (16)
N14—C60—H60118.6N8—Pd3—Pd480.80 (15)
C59—C60—H60118.6N13—Pd4—O4179.0 (2)
N15—C61—C62178 (2)N13—Pd4—N1481.1 (2)
C61—C62—H62A110.0O4—Pd4—N1499.6 (2)
C61—C62—H62B109.3N13—Pd4—N1281.0 (2)
H62A—C62—H62B109.4O4—Pd4—N1298.3 (2)
C61—C62—H62C109.3N14—Pd4—N12161.9 (2)
H62A—C62—H62C109.4N13—Pd4—Pd3100.39 (15)
H62B—C62—H62C109.4O4—Pd4—Pd380.48 (14)
C1—N1—C5119.3 (6)N14—Pd4—Pd381.66 (15)
C1—N1—Pd1127.5 (5)N12—Pd4—Pd3103.64 (14)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···F330.932.523.313 (12)144
C3—H3···F13iii0.932.473.402 (12)176
C7—H7···F44iv0.932.453.223 (13)140
C14—H14···F130.932.543.246 (11)133
C16—H16···F330.932.323.051 (11)135
C17—H17···F34v0.932.463.291 (11)150
C18—H18···F12iii0.932.523.251 (12)135
C22—H22···F43iv0.932.453.104 (11)127
C24—H24···F52vi0.932.493.367 (9)157
C30—H30···F150.932.393.192 (9)145
C34—H34···N15iii0.932.473.157 (16)131
C38—H38···F71vii0.932.333.159 (12)148
C39—H39···F62viii0.932.543.474 (13)179
C48—H48···F54iii0.932.423.129 (11)133
C52—H52···F31v0.932.463.254 (11)143
C54—H54···F11viii0.932.393.304 (10)166
C60—H60···F510.932.343.188 (9)151
Symmetry codes: (iii) x+1, y, z; (iv) x+2, y+1, z+1; (v) x+2, y+1, z; (vi) x+1, y+1, z+1; (vii) x, y+1, z; (viii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Pd2(C15H11N3)2NO3]PF6·C2H3N
Mr2393.57
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)14.0633 (3), 14.7277 (4), 20.7043 (7)
α, β, γ (°)104.681 (4), 90.450 (1), 102.226 (3)
V3)4045.6 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.14
Crystal size (mm)0.32 × 0.28 × 0.25
Data collection
DiffractometerRigaku R-AXIS RAPID IP
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.71, 0.76
No. of measured, independent and
observed [I > 2σ(I)] reflections
27513, 17102, 13353
Rint0.042
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.156, 1.07
No. of reflections17102
No. of parameters1165
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0584P)2 + 15.4804P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.97, 0.61

Computer programs: RAPID-AUTO (Rigaku, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···F330.932.523.313 (12)143.5
C3—H3···F13i0.932.473.402 (12)176.1
C7—H7···F44ii0.932.453.223 (13)140.2
C14—H14···F130.932.543.246 (11)132.9
C16—H16···F330.932.323.051 (11)134.8
C17—H17···F34iii0.932.463.291 (11)149.6
C18—H18···F12i0.932.523.251 (12)135.4
C22—H22···F43ii0.932.453.104 (11)127.4
C24—H24···F52iv0.932.493.367 (9)156.6
C30—H30···F150.932.393.192 (9)144.5
C34—H34···N15i0.932.473.157 (16)131.2
C38—H38···F71v0.932.333.159 (12)147.5
C39—H39···F62vi0.932.543.474 (13)179.1
C48—H48···F54i0.932.423.129 (11)132.8
C52—H52···F31iii0.932.463.254 (11)142.9
C54—H54···F11vi0.932.393.304 (10)166.3
C60—H60···F510.932.343.188 (9)151.3
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+1; (iii) x+2, y+1, z; (iv) x+1, y+1, z+1; (v) x, y+1, z; (vi) x+1, y+1, z.
 

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