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The crystal structure of the title compound, (2,2′-bipyridyl-κ2N,N′)(tetra­allyl 3,3,3′,3′-tetra­methyl-1,1′-bi­cyclo­propane-1,1′,2,2′-tetra­carboxyl­ato-κ2C2,C2′)­palladium(II), [Pd(C26H32­O8)(C10­H8­N2)], is disordered above 194 K. A doubling of the unit cell is observed on cooling. The structure at 143 K contains two ordered mol­ecules related by a pseudo-translation vector of approximately (0.44,0.00,0.50) or a pseudo-inversion center at approximately (0.22,0.00,0.25). Weak intermolecular C—H...O interactions are enhanced in the low-temperature structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006193/fg1601sup1.cif
Contains datablocks default, I143K, I205K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006193/fg1601I143Ksup2.hkl
Contains datablock I143K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006193/fg1601I205Ksup3.hkl
Contains datablock I205K

CCDC references: 147634; 147635

Comment top

In our effort to synthesize the first palladepane-derivatives and in the course of an investigation covering polymer-bound organometallic catalysts we reacted diallyl 3,3-dimethylcyclopropene-1,2-dicarboxylate with a Pd(0)-compound. One of the two products was the desired palladepane-derivative, the other one turned out to be the title compound, (I) (Hashmi et al., 1999). (I) is also a promising substrate for the formation of polymer-bound organometallic catalysts by co-metathesis with other 1,n-dienes. During X-ray diffraction experiments on (I) a reversible phase transition was observed at 194 K. The crystal structure of the high-temperature phase has been determined at room temperature (292 K) and at 205 K. The high-temperature phase has one molecule in the asymmetric unit (Fig. 1). Two propene side chains are disordered. The structures at 292 K and 205 K are similar. Thus the room temperature results are not reported here. \sch

The crystal structure of the low-temperature phase has been determined at 143 K. The crystal structure at this temperature contains two independent, ordered molecules (Fig. 2). The cell axes transform according to alow = ahigh, blow = −chigh and clow = 2bhigh − ahigh. The fractional coordinates between the low- and the high-temperature phases are related by: xlow = xhigh + 0.5yhigh, ylow = −zhigh and zlow = 0.5yhigh. Thus the low-temperature structure should be approximately B-centered. Surprisingly, the reflection intensities do not show approximate B-centering. The two independent molecules are related by a pseudo-translation of about (0.44 0.00 1/2).

A combination of this pseudo-translation vector with the crystallographic inversion center at 000 results at a non-crystallographic pseudo-inversion center at 0.22 0.00 0.25 (Desiraju et al., 1991). The presence of this pseudo-center is confirmed by program BUNYIP (Hester & Hall, 1996). The conformations of both independent molecules are very similar. The molecules differ mainly in the orientations of the propene groups attached to O2, O10, O8 and O16. Those are the propene groups which are disordered above the phase-transition temperature. Below the phase-transition temperature both molecules are fully ordered. The conformations of the molecules in the high-temperature and low-temperature phases are compared in Fig. 3. This figure shows the relative positions of the molecules of the low-temperature structure as they would appear in the high-temperature cell. The phase transition not only corresponds to an order-disorder transition of the two propene side chains, but also results in small translations of the molecules along a. Thus the deviation from ideal B-centering of the low-temperature structure results from molecular rearrangements at the phase transition. Both molecules approximately have C2 symmetry. The propene side chains, however, show considerable deviations from this C2 symmetry. The bipyridyl groups are non-planar: the angle between the planes of the pyridyl groups is 15.6 (1) for molecule 1 and 11.0 (1) for molecule 2. The Pd atoms have heavily distorted square-planar conformations. The angle between the C—Pd—C plane and the N—Pd—N plane is 16.9 (1) for molecule 1 and 15.0 (1) for molecule 2. The non-planarity of the Pd atoms may result from intramolecular C—H···O interactions: O1···H27 2.33, O7···H36 2.41, O9···H63 2.28 and O15···H72 2.39 (see Table 1 for intra- and intermolecular C—H···O interactions).

Intramolecular C—H···O interactions very similar to those in the title compound have been observed in the crystal structures of related palladatricyclo[4.1.0.02,4]heptanes (Hashmi, Naumann & Bats, 1997; Hashmi, Naumann et al., 1997; Hashmi, Naumann & Bolte, 1998; Hashmi, Naumann et al., 1998; Hashmi, Bats et al., 1998). Thus these interactions appear characteristic for this group. The crystal packing shows a number of weak, intermolecular C—H···O interactions with H···O distances between 2.5 and 2.6 Å. These interactions have been included in Table 1. Desiraju & Steiner (1999) have outlined the significance of such weak, intermolecular interactions for crystal packing. All four weak, intermolecular C—H···O interactions involve propene side chains. In the high-temperature structure such weak, intermolecular C—H···O interactions are only observed for two partially occupied propene groups (Table 2). Thus the phase transition results in an enhancement of intermolecular C—H···O interactions below the transition temperature. A determination of the cell constants just above and below the phase transition temperature shows no significant change in the volume occupied by a molecule. A similar result has been reported for an order-disorder transition by Thuéry et al. (1999). Herbstein & Samson (1994) showed this to be a prerequisite for a second-order transition.

Experimental top

(I) was prepared as described by Hashmi et al. (1999). Suitable crystals were obtained by crystallization from hexane/dichloromethane at 277 K.

Refinement top

Two side chains of the 205 K structure were refined with split atoms. The occupancy factor was 0.613 (7) for C6, C7 and C8 and 0.387 (7) for C6', C7' and C8'. An occupancy factor of 0.596 (9) was found for C25 and C26, while 0.404 (9) was used for C25' and C26'. Only a single position was found for C24. The split atoms C25, C26, C25' and C26' still had rather large displacement parameters and thus were refined with anisotropic displacement parameters to reduce residual density near this group. The H atoms in both determinations were placed at calculated positions and were refined with fixed individual displacement parameters [U(H) = 1.2Ueq(C) and U(H) = 1.5Ueq(Cmethyl)] using a riding model with fixed distances: HC(methyl) = 0.96, H—C(secondary) = 0.97 and H—C(planar) = 0.93 Å, respectively. Torsion angles about the C—C bonds of the methyl groups were allowed to refine.

Computing details top

For both compounds, data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS96 (Sheldrick, 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1996); software used to prepare material for publication: CIF in SHELXL97.

Figures top
[Figure 1] Fig. 1. The structures of the two independent molecules of (I) at 143 K with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The structure of the partly disordered molecule of (I) at 205 K with 50% probability displacement ellipsoids.
[Figure 3] Fig. 3. The relative positions of the two independent molecules of the low-temperature structure (open lines: molecule 1, dashed lines: molecule 2) transformed to the high-temperature setting (solid lines: disordered molecule at 205 K).
(I143K) tetraallyl (2,2'-bipyridyl)-rac-3,3,7,7-tetramethyl-trans-5-palladatricyclo [4.1.0.02,4]heptane-1,2,4,6-tetracarboxylate top
Crystal data top
[Pd(C10H8N2)(C26H32O8)]Z = 4
Mr = 735.10F(000) = 1520
Triclinic, P1Dx = 1.435 Mg m3
a = 9.0197 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 17.918 (2) ÅCell parameters from 276 reflections
c = 21.375 (3) Åθ = 3–23°
α = 95.641 (12)°µ = 0.60 mm1
β = 97.375 (11)°T = 143 K
γ = 93.083 (9)°Plate, yellow
V = 3401.7 (7) Å30.44 × 0.17 × 0.04 mm
Data collection top
SIEMENS SMART
diffractometer
22046 independent reflections
Radiation source: sealed tube16183 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ω scansθmax = 32.2°, θmin = 1.4°
Absorption correction: numerical (SHELXTL; sheldrick, 1996)
?
h = 1313
Tmin = 0.817, Tmax = 0.977k = 2624
64204 measured reflectionsl = 3231
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max = 0.010
22046 reflectionsΔρmax = 0.56 e Å3
856 parametersΔρmin = 0.61 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00053 (14)
Crystal data top
[Pd(C10H8N2)(C26H32O8)]γ = 93.083 (9)°
Mr = 735.10V = 3401.7 (7) Å3
Triclinic, P1Z = 4
a = 9.0197 (6) ÅMo Kα radiation
b = 17.918 (2) ŵ = 0.60 mm1
c = 21.375 (3) ÅT = 143 K
α = 95.641 (12)°0.44 × 0.17 × 0.04 mm
β = 97.375 (11)°
Data collection top
SIEMENS SMART
diffractometer
22046 independent reflections
Absorption correction: numerical (SHELXTL; sheldrick, 1996)
?
16183 reflections with I > 2σ(I)
Tmin = 0.817, Tmax = 0.977Rint = 0.059
64204 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.21Δρmax = 0.56 e Å3
22046 reflectionsΔρmin = 0.61 e Å3
856 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pd10.017816 (18)0.339624 (9)0.210874 (7)0.01716 (5)
Pd20.552762 (17)0.346667 (8)0.286322 (7)0.01484 (5)
C500.1130 (3)0.04246 (15)0.38086 (13)0.0349 (6)
H500.03700.01100.37340.042*
O50.02199 (18)0.23621 (9)0.01307 (7)0.0240 (3)
O130.47474 (18)0.24308 (8)0.48821 (7)0.0233 (3)
O120.33265 (17)0.10344 (8)0.34456 (7)0.0223 (3)
O140.55946 (18)0.13684 (8)0.42685 (7)0.0215 (3)
O110.44905 (19)0.08494 (9)0.24432 (8)0.0277 (4)
O90.6658 (2)0.18947 (9)0.15352 (7)0.0287 (4)
O80.12367 (17)0.36104 (9)0.07704 (7)0.0221 (3)
O20.17079 (18)0.21406 (9)0.29772 (7)0.0261 (4)
O150.38639 (17)0.41565 (8)0.45781 (7)0.0231 (3)
N30.6933 (2)0.38044 (10)0.20910 (8)0.0203 (4)
O40.20322 (19)0.09745 (9)0.14295 (7)0.0259 (4)
N40.4981 (2)0.46486 (10)0.29504 (8)0.0175 (4)
O160.62108 (17)0.36342 (8)0.43559 (7)0.0202 (3)
O10.06365 (19)0.18332 (9)0.34619 (7)0.0285 (4)
O100.42252 (19)0.22548 (9)0.18319 (7)0.0277 (4)
N10.0819 (2)0.38040 (11)0.29515 (8)0.0221 (4)
C20.0231 (2)0.17923 (12)0.17924 (9)0.0174 (4)
O70.10524 (18)0.41115 (9)0.03601 (7)0.0259 (4)
O30.1032 (2)0.07676 (9)0.24523 (7)0.0288 (4)
N20.0975 (2)0.45329 (10)0.19685 (9)0.0206 (4)
C370.5840 (2)0.23238 (11)0.26334 (9)0.0159 (4)
C400.4446 (2)0.31820 (11)0.37041 (9)0.0156 (4)
C10.0245 (2)0.22624 (12)0.23439 (10)0.0177 (4)
O60.05328 (19)0.12615 (9)0.07475 (7)0.0248 (3)
C310.0612 (3)0.45555 (13)0.29584 (10)0.0230 (5)
C680.5654 (2)0.50048 (12)0.24730 (10)0.0189 (4)
C90.1428 (2)0.17759 (12)0.21125 (10)0.0189 (4)
C450.6890 (2)0.18336 (12)0.29370 (10)0.0182 (4)
C50.0200 (3)0.20354 (12)0.29793 (10)0.0220 (5)
C390.4546 (2)0.23290 (11)0.37639 (9)0.0153 (4)
C30.0637 (2)0.22579 (11)0.11613 (10)0.0168 (4)
C380.5170 (2)0.18606 (11)0.31568 (9)0.0153 (4)
C560.3022 (2)0.27818 (12)0.37795 (10)0.0176 (4)
C520.4944 (2)0.20678 (12)0.43631 (10)0.0177 (4)
C670.6827 (2)0.45501 (12)0.20271 (10)0.0186 (4)
C100.2131 (3)0.10501 (12)0.24916 (11)0.0255 (5)
H10A0.29950.11580.27710.038*
H10B0.14140.08290.27360.038*
H10C0.24250.07060.22060.038*
C480.4343 (2)0.11937 (12)0.29645 (10)0.0192 (4)
C460.7672 (3)0.11107 (12)0.25873 (11)0.0243 (5)
H46A0.85930.12210.23470.037*
H46B0.78820.07690.28880.037*
H46C0.70350.08860.23060.037*
C110.2575 (2)0.21468 (13)0.17425 (11)0.0244 (5)
H11A0.33720.23020.20330.037*
H11B0.29750.17950.14870.037*
H11C0.21010.25770.14740.037*
C710.3377 (3)0.57628 (13)0.32926 (11)0.0267 (5)
H710.25950.60070.35780.032*
C720.3866 (3)0.50296 (12)0.33514 (10)0.0220 (5)
H720.34010.47910.36830.026*
C580.2159 (2)0.26374 (13)0.32205 (10)0.0222 (5)
H58A0.14390.30510.32180.033*
H58B0.28420.25860.28330.033*
H58C0.16500.21830.32560.033*
C320.0524 (3)0.49371 (12)0.24523 (11)0.0243 (5)
C410.5656 (3)0.21133 (12)0.19543 (10)0.0205 (4)
C650.8821 (3)0.43972 (14)0.11654 (11)0.0283 (5)
H650.94380.45950.08490.034*
C630.8000 (3)0.33690 (13)0.17059 (11)0.0256 (5)
H630.81140.28620.17630.031*
C240.1834 (2)0.40113 (13)0.02438 (11)0.0238 (5)
H24A0.15020.38070.01500.029*
H24B0.15090.45410.02010.029*
C120.1089 (2)0.11250 (12)0.19369 (10)0.0212 (4)
C470.7885 (2)0.22102 (13)0.33801 (11)0.0239 (5)
H47A0.87580.23680.31350.036*
H47B0.73400.26400.36250.036*
H47C0.81840.18610.36600.036*
C570.1932 (3)0.28997 (13)0.43928 (11)0.0240 (5)
H57A0.13160.33550.44000.036*
H57B0.13100.24820.44170.036*
H57C0.24840.29360.47490.036*
C160.0054 (2)0.19909 (12)0.06213 (10)0.0195 (4)
C200.2190 (2)0.27098 (12)0.10127 (10)0.0191 (4)
C210.2940 (3)0.28175 (14)0.03293 (10)0.0256 (5)
H21A0.35230.32900.02520.038*
H21B0.21890.28140.00500.038*
H21C0.35830.24170.02540.038*
C600.6515 (3)0.39672 (13)0.49713 (10)0.0230 (5)
H60A0.62810.45060.50150.028*
H60B0.59040.37550.53080.028*
C340.2262 (3)0.59726 (15)0.20007 (13)0.0372 (6)
H340.26870.64550.20110.045*
C40.0807 (2)0.31049 (12)0.12147 (10)0.0176 (4)
C690.5217 (3)0.57390 (13)0.23925 (11)0.0274 (5)
H690.56980.59720.20600.033*
C130.3012 (3)0.03797 (15)0.15626 (13)0.0384 (7)
H13A0.24320.01000.16490.046*
H13B0.34820.04680.19350.046*
C590.4755 (2)0.36980 (12)0.42563 (10)0.0182 (4)
C660.7781 (3)0.48577 (13)0.15745 (10)0.0239 (5)
H660.77180.53730.15480.029*
C270.1829 (3)0.34216 (14)0.34013 (11)0.0273 (5)
H270.19790.29050.33960.033*
C490.2331 (3)0.04637 (14)0.32732 (12)0.0314 (6)
H49A0.18930.05850.29010.038*
H49B0.28900.00200.31710.038*
C180.1690 (3)0.01357 (16)0.04842 (15)0.0431 (7)
H180.22200.01270.02210.052*
C350.2721 (3)0.55546 (14)0.15128 (13)0.0330 (6)
H350.34710.57490.11890.040*
C640.8939 (3)0.36398 (14)0.12287 (11)0.0280 (5)
H640.96340.33180.09570.034*
C280.2655 (3)0.37592 (15)0.38720 (11)0.0303 (5)
H280.33290.34740.41810.036*
C530.6093 (3)0.10828 (13)0.48209 (11)0.0285 (5)
H53A0.68270.14010.49800.034*
H53B0.52500.10860.51530.034*
C360.2050 (3)0.48408 (13)0.15106 (12)0.0263 (5)
H360.23590.45640.11770.032*
C610.8121 (3)0.38028 (16)0.50108 (12)0.0337 (6)
H610.85390.33190.48750.040*
C230.0274 (2)0.36465 (12)0.07303 (10)0.0197 (4)
C290.2462 (3)0.45242 (15)0.38742 (12)0.0346 (6)
H290.30150.47670.41820.042*
C220.3331 (3)0.25940 (14)0.14744 (11)0.0245 (5)
H22A0.39510.30490.14620.037*
H22B0.39450.21960.13570.037*
H22C0.28170.24640.18960.037*
C700.4064 (3)0.61240 (13)0.28069 (11)0.0312 (6)
H700.37590.66170.27580.037*
C190.1359 (4)0.02453 (16)0.09808 (14)0.0486 (8)
H19A0.08310.00120.12620.058*
H19B0.16480.07560.10600.058*
C170.1327 (3)0.09460 (14)0.02819 (12)0.0337 (6)
H17A0.07110.10120.01290.040*
H17B0.22410.11990.02450.040*
C70.3896 (3)0.17404 (14)0.33666 (12)0.0318 (6)
H70.41500.14480.30380.038*
C60.2281 (3)0.18535 (15)0.35501 (11)0.0325 (6)
H6A0.17440.13820.37290.039*
H6B0.21660.22100.38640.039*
C330.1154 (3)0.56587 (13)0.24736 (12)0.0335 (6)
H330.08270.59310.28080.040*
C140.4173 (3)0.03609 (16)0.10108 (13)0.0407 (7)
H140.49150.00270.10590.049*
C150.4265 (3)0.07680 (16)0.04595 (13)0.0411 (7)
H15A0.35510.11110.03880.049*
H15B0.50450.07140.01410.049*
C550.6852 (3)0.00957 (15)0.41025 (14)0.0408 (7)
H55A0.64600.01030.37680.049*
H55B0.73040.05810.40460.049*
C540.6770 (3)0.03033 (14)0.46466 (13)0.0360 (6)
H540.71800.00770.49640.043*
C250.3475 (3)0.39059 (16)0.03988 (12)0.0326 (6)
H25A0.39280.34220.04340.039*
C510.1028 (3)0.07899 (16)0.43796 (14)0.0411 (7)
H51A0.17590.11120.44780.049*
H51B0.02240.07260.46840.049*
C620.8977 (3)0.42987 (19)0.52260 (14)0.0511 (9)
H62A0.85860.47860.53650.061*
H62B0.99820.41670.52410.061*
C300.1433 (3)0.49290 (14)0.34122 (11)0.0320 (6)
H300.12900.54480.34050.038*
C440.1396 (4)0.19133 (19)0.15457 (17)0.0554 (9)
H44A0.16400.18310.19440.066*
H44B0.04120.18850.14630.066*
C80.4976 (3)0.20279 (16)0.36398 (13)0.0414 (7)
H8A0.47550.23230.39700.050*
H8B0.59650.19380.35040.050*
C260.4323 (3)0.44696 (19)0.04893 (14)0.0492 (8)
H26A0.38900.49570.04560.059*
H26B0.53570.43810.05860.059*
C420.4024 (4)0.21290 (18)0.11694 (12)0.0455 (8)
H42A0.43930.25440.09480.055*
H42B0.45930.16710.09760.055*
C430.2413 (4)0.20645 (17)0.11121 (15)0.0483 (8)
H430.21140.21420.07220.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01947 (9)0.01368 (8)0.01753 (8)0.00030 (6)0.00052 (6)0.00197 (6)
Pd20.01687 (8)0.01167 (8)0.01484 (8)0.00044 (6)0.00138 (6)0.00056 (6)
C500.0320 (14)0.0297 (14)0.0446 (16)0.0110 (11)0.0028 (12)0.0108 (12)
O50.0299 (9)0.0239 (8)0.0178 (8)0.0011 (7)0.0055 (7)0.0019 (6)
O130.0351 (9)0.0169 (8)0.0168 (7)0.0009 (7)0.0014 (7)0.0009 (6)
O120.0275 (8)0.0181 (8)0.0222 (8)0.0109 (7)0.0028 (6)0.0016 (6)
O140.0298 (9)0.0161 (7)0.0183 (7)0.0039 (6)0.0044 (6)0.0019 (6)
O110.0354 (10)0.0222 (8)0.0236 (8)0.0070 (7)0.0025 (7)0.0079 (7)
O90.0383 (10)0.0256 (9)0.0184 (8)0.0031 (8)0.0037 (7)0.0030 (7)
O80.0210 (8)0.0214 (8)0.0220 (8)0.0049 (6)0.0004 (6)0.0063 (6)
O20.0286 (9)0.0315 (9)0.0172 (8)0.0008 (7)0.0057 (7)0.0035 (7)
O150.0252 (8)0.0185 (8)0.0226 (8)0.0029 (7)0.0014 (6)0.0041 (6)
N30.0236 (10)0.0174 (9)0.0189 (9)0.0033 (8)0.0023 (7)0.0025 (7)
O40.0330 (9)0.0251 (9)0.0199 (8)0.0142 (7)0.0006 (7)0.0007 (7)
N40.0188 (9)0.0166 (9)0.0170 (8)0.0001 (7)0.0029 (7)0.0012 (7)
O160.0205 (8)0.0204 (8)0.0177 (7)0.0022 (6)0.0010 (6)0.0059 (6)
O10.0330 (9)0.0313 (9)0.0185 (8)0.0030 (8)0.0041 (7)0.0020 (7)
O100.0334 (10)0.0307 (9)0.0177 (8)0.0042 (7)0.0073 (7)0.0056 (7)
N10.0258 (10)0.0217 (10)0.0191 (9)0.0038 (8)0.0014 (8)0.0045 (8)
C20.0223 (11)0.0149 (10)0.0150 (10)0.0042 (8)0.0018 (8)0.0004 (8)
O70.0258 (9)0.0223 (8)0.0260 (8)0.0023 (7)0.0002 (7)0.0079 (7)
O30.0391 (10)0.0244 (9)0.0214 (8)0.0123 (8)0.0005 (7)0.0051 (7)
N20.0215 (9)0.0157 (9)0.0245 (9)0.0004 (7)0.0037 (8)0.0017 (7)
C370.0206 (10)0.0113 (9)0.0147 (9)0.0001 (8)0.0003 (8)0.0001 (8)
C400.0188 (10)0.0129 (9)0.0137 (9)0.0006 (8)0.0016 (8)0.0008 (8)
C10.0202 (11)0.0148 (10)0.0170 (10)0.0016 (8)0.0010 (8)0.0009 (8)
O60.0353 (9)0.0170 (8)0.0236 (8)0.0006 (7)0.0095 (7)0.0031 (6)
C310.0307 (12)0.0210 (11)0.0198 (11)0.0061 (10)0.0088 (9)0.0045 (9)
C680.0229 (11)0.0181 (10)0.0161 (10)0.0021 (9)0.0047 (8)0.0000 (8)
C90.0202 (11)0.0157 (10)0.0192 (10)0.0007 (8)0.0014 (8)0.0009 (8)
C450.0201 (11)0.0149 (10)0.0182 (10)0.0010 (8)0.0005 (8)0.0014 (8)
C50.0285 (12)0.0161 (10)0.0208 (11)0.0014 (9)0.0017 (9)0.0011 (9)
C390.0162 (10)0.0130 (9)0.0163 (9)0.0028 (8)0.0008 (8)0.0006 (8)
C30.0184 (10)0.0147 (10)0.0171 (10)0.0031 (8)0.0010 (8)0.0011 (8)
C380.0186 (10)0.0116 (9)0.0148 (9)0.0013 (8)0.0003 (8)0.0015 (8)
C560.0172 (10)0.0142 (10)0.0203 (10)0.0003 (8)0.0000 (8)0.0006 (8)
C520.0188 (10)0.0167 (10)0.0178 (10)0.0038 (8)0.0016 (8)0.0023 (8)
C670.0223 (11)0.0177 (10)0.0164 (10)0.0047 (9)0.0038 (8)0.0016 (8)
C100.0283 (12)0.0176 (11)0.0281 (12)0.0012 (9)0.0009 (10)0.0024 (9)
C480.0212 (11)0.0146 (10)0.0216 (11)0.0013 (8)0.0029 (9)0.0014 (8)
C460.0256 (12)0.0198 (11)0.0250 (12)0.0053 (9)0.0008 (9)0.0014 (9)
C110.0175 (11)0.0233 (12)0.0304 (12)0.0004 (9)0.0010 (9)0.0034 (10)
C710.0304 (13)0.0221 (12)0.0254 (12)0.0076 (10)0.0031 (10)0.0027 (10)
C720.0233 (11)0.0197 (11)0.0221 (11)0.0011 (9)0.0004 (9)0.0020 (9)
C580.0190 (11)0.0222 (11)0.0258 (11)0.0005 (9)0.0042 (9)0.0043 (9)
C320.0321 (13)0.0161 (11)0.0269 (12)0.0029 (9)0.0111 (10)0.0025 (9)
C410.0314 (12)0.0121 (10)0.0169 (10)0.0004 (9)0.0017 (9)0.0006 (8)
C650.0288 (13)0.0350 (14)0.0215 (11)0.0097 (11)0.0014 (9)0.0075 (10)
C630.0274 (12)0.0178 (11)0.0284 (12)0.0009 (9)0.0071 (10)0.0012 (9)
C240.0213 (11)0.0238 (12)0.0242 (11)0.0021 (9)0.0010 (9)0.0056 (9)
C120.0230 (11)0.0189 (11)0.0222 (11)0.0039 (9)0.0034 (9)0.0033 (9)
C470.0169 (11)0.0248 (12)0.0291 (12)0.0022 (9)0.0039 (9)0.0017 (10)
C570.0219 (11)0.0214 (11)0.0257 (12)0.0006 (9)0.0066 (9)0.0007 (9)
C160.0193 (11)0.0194 (11)0.0200 (10)0.0033 (9)0.0002 (8)0.0045 (9)
C200.0184 (10)0.0187 (11)0.0190 (10)0.0008 (8)0.0000 (8)0.0006 (8)
C210.0216 (11)0.0299 (13)0.0233 (11)0.0021 (10)0.0013 (9)0.0008 (10)
C600.0293 (12)0.0218 (11)0.0163 (10)0.0029 (9)0.0021 (9)0.0058 (9)
C340.0477 (17)0.0220 (13)0.0440 (16)0.0067 (12)0.0182 (13)0.0031 (11)
C40.0188 (10)0.0148 (10)0.0183 (10)0.0004 (8)0.0001 (8)0.0011 (8)
C690.0411 (14)0.0173 (11)0.0242 (12)0.0012 (10)0.0041 (10)0.0052 (9)
C130.0472 (16)0.0350 (15)0.0335 (14)0.0282 (13)0.0007 (12)0.0011 (12)
C590.0226 (11)0.0148 (10)0.0168 (10)0.0029 (9)0.0003 (8)0.0025 (8)
C660.0301 (12)0.0204 (11)0.0218 (11)0.0081 (10)0.0012 (9)0.0051 (9)
C270.0284 (13)0.0266 (13)0.0254 (12)0.0032 (10)0.0026 (10)0.0022 (10)
C490.0366 (14)0.0247 (13)0.0348 (14)0.0155 (11)0.0082 (11)0.0004 (11)
C180.0514 (18)0.0305 (15)0.0505 (18)0.0074 (13)0.0160 (15)0.0125 (13)
C350.0283 (13)0.0262 (13)0.0417 (15)0.0086 (11)0.0056 (11)0.0057 (11)
C640.0264 (12)0.0293 (13)0.0244 (12)0.0016 (10)0.0071 (10)0.0023 (10)
C280.0306 (13)0.0384 (15)0.0217 (12)0.0086 (11)0.0000 (10)0.0030 (10)
C530.0404 (15)0.0248 (12)0.0223 (11)0.0033 (11)0.0107 (10)0.0063 (10)
C360.0246 (12)0.0212 (12)0.0325 (13)0.0003 (10)0.0013 (10)0.0034 (10)
C610.0285 (13)0.0393 (15)0.0295 (13)0.0061 (11)0.0051 (11)0.0115 (11)
C230.0212 (11)0.0175 (10)0.0194 (10)0.0020 (9)0.0013 (8)0.0017 (8)
C290.0435 (16)0.0415 (16)0.0224 (12)0.0178 (13)0.0047 (11)0.0128 (11)
C220.0205 (11)0.0302 (13)0.0223 (11)0.0001 (10)0.0029 (9)0.0011 (10)
C700.0471 (16)0.0163 (11)0.0297 (13)0.0073 (11)0.0080 (11)0.0016 (10)
C190.068 (2)0.0296 (15)0.0422 (17)0.0154 (15)0.0051 (15)0.0009 (13)
C170.0441 (16)0.0284 (13)0.0328 (13)0.0005 (12)0.0188 (12)0.0079 (11)
C70.0402 (15)0.0294 (13)0.0261 (12)0.0031 (11)0.0091 (11)0.0016 (10)
C60.0392 (15)0.0362 (15)0.0214 (12)0.0009 (12)0.0092 (11)0.0050 (11)
C330.0538 (17)0.0183 (12)0.0310 (13)0.0002 (11)0.0133 (12)0.0068 (10)
C140.0419 (16)0.0414 (16)0.0412 (16)0.0219 (13)0.0020 (13)0.0098 (13)
C150.0423 (16)0.0402 (16)0.0401 (16)0.0097 (13)0.0047 (13)0.0113 (13)
C550.0534 (18)0.0241 (13)0.0427 (16)0.0083 (13)0.0002 (14)0.0073 (12)
C540.0463 (17)0.0263 (13)0.0377 (15)0.0059 (12)0.0111 (13)0.0115 (11)
C250.0237 (12)0.0380 (15)0.0332 (14)0.0018 (11)0.0001 (10)0.0057 (11)
C510.0386 (16)0.0400 (16)0.0454 (17)0.0067 (13)0.0008 (13)0.0135 (14)
C620.0242 (14)0.074 (2)0.0479 (18)0.0009 (14)0.0017 (13)0.0246 (17)
C300.0474 (16)0.0250 (13)0.0280 (13)0.0106 (12)0.0114 (12)0.0111 (10)
C440.056 (2)0.057 (2)0.055 (2)0.0069 (17)0.0232 (18)0.0059 (17)
C80.0450 (17)0.0475 (18)0.0306 (14)0.0053 (14)0.0097 (12)0.0025 (13)
C260.0297 (15)0.065 (2)0.0548 (19)0.0159 (15)0.0063 (13)0.0056 (16)
C420.0553 (19)0.058 (2)0.0215 (13)0.0083 (15)0.0159 (13)0.0098 (13)
C430.069 (2)0.0387 (17)0.0391 (17)0.0086 (16)0.0296 (16)0.0098 (13)
Geometric parameters (Å, º) top
Pd1—C12.048 (2)O6—C161.345 (3)
Pd1—C42.048 (2)O6—C171.440 (3)
Pd1—N22.1028 (18)C31—C301.391 (3)
Pd1—N12.1217 (18)C31—C321.477 (3)
Pd2—C372.054 (2)C68—C691.386 (3)
Pd2—C402.056 (2)C68—C671.479 (3)
Pd2—N32.1070 (18)C9—C111.522 (3)
Pd2—N42.1331 (18)C9—C101.524 (3)
C50—C511.317 (4)C45—C461.520 (3)
C50—C491.481 (4)C45—C471.522 (3)
O5—C161.216 (2)C45—C381.559 (3)
O13—C521.217 (2)C39—C521.485 (3)
O12—C481.350 (3)C39—C381.501 (3)
O12—C491.449 (3)C39—C561.553 (3)
O14—C521.340 (2)C3—C161.487 (3)
O14—C531.445 (3)C3—C41.534 (3)
O11—C481.207 (3)C3—C201.560 (3)
O9—C411.207 (3)C38—C481.494 (3)
O8—C231.352 (3)C56—C581.517 (3)
O8—C241.453 (3)C56—C571.524 (3)
O2—C51.363 (3)C67—C661.387 (3)
O2—C61.449 (3)C71—C701.375 (4)
O15—C591.212 (3)C71—C721.386 (3)
N3—C631.343 (3)C32—C331.391 (3)
N3—C671.356 (3)C65—C661.375 (3)
O4—C121.348 (3)C65—C641.377 (3)
O4—C131.450 (3)C63—C641.383 (3)
N4—C721.342 (3)C24—C251.472 (3)
N4—C681.352 (3)C20—C41.504 (3)
O16—C591.357 (3)C20—C211.518 (3)
O16—C601.455 (2)C20—C221.523 (3)
O1—C51.209 (3)C60—C611.477 (3)
O10—C411.365 (3)C34—C351.377 (4)
O10—C421.448 (3)C34—C331.380 (4)
N1—C271.342 (3)C4—C231.492 (3)
N1—C311.351 (3)C69—C701.382 (3)
C2—C121.488 (3)C13—C141.478 (4)
C2—C31.506 (3)C27—C281.382 (3)
C2—C11.545 (3)C18—C191.282 (4)
C2—C91.561 (3)C18—C171.480 (4)
O7—C231.216 (3)C35—C361.386 (3)
O3—C121.212 (3)C28—C291.373 (4)
N2—C361.340 (3)C53—C541.487 (3)
N2—C321.353 (3)C61—C621.297 (4)
C37—C411.496 (3)C29—C301.384 (4)
C37—C451.506 (3)C7—C81.306 (4)
C37—C381.539 (3)C7—C61.488 (4)
C40—C591.491 (3)C14—C151.314 (4)
C40—C561.503 (3)C55—C541.295 (4)
C40—C391.545 (3)C25—C261.314 (4)
C1—C51.490 (3)C44—C431.277 (5)
C1—C91.505 (3)C42—C431.484 (4)
C1—Pd1—C484.24 (8)C2—C3—C4113.42 (17)
C1—Pd1—N2168.62 (8)C16—C3—C20118.02 (18)
C4—Pd1—N299.22 (8)C2—C3—C20119.23 (17)
C1—Pd1—N1100.46 (8)C4—C3—C2058.17 (13)
C4—Pd1—N1168.54 (8)C48—C38—C39117.10 (18)
N2—Pd1—N178.21 (7)C48—C38—C37117.95 (17)
C37—Pd2—C4083.88 (8)C39—C38—C37113.61 (16)
C37—Pd2—N398.56 (8)C48—C38—C45118.15 (17)
C40—Pd2—N3170.27 (7)C39—C38—C45118.48 (17)
C37—Pd2—N4169.19 (7)C37—C38—C4558.19 (13)
C40—Pd2—N4101.36 (7)C40—C56—C58120.05 (18)
N3—Pd2—N477.86 (7)C40—C56—C57121.55 (18)
C51—C50—C49126.7 (2)C58—C56—C57109.55 (18)
C48—O12—C49114.73 (17)C40—C56—C3960.72 (13)
C52—O14—C53115.45 (16)C58—C56—C39118.09 (17)
C23—O8—C24115.52 (16)C57—C56—C39119.55 (18)
C5—O2—C6116.15 (18)O13—C52—O14122.39 (19)
C63—N3—C67118.11 (19)O13—C52—C39125.9 (2)
C63—N3—Pd2126.17 (15)O14—C52—C39111.66 (17)
C67—N3—Pd2115.37 (14)N3—C67—C66121.3 (2)
C12—O4—C13114.34 (17)N3—C67—C68115.78 (19)
C72—N4—C68117.89 (19)C66—C67—C68122.9 (2)
C72—N4—Pd2126.41 (15)O11—C48—O12122.82 (19)
C68—N4—Pd2114.46 (14)O11—C48—C38125.8 (2)
C59—O16—C60115.29 (16)O12—C48—C38111.27 (17)
C41—O10—C42114.86 (19)C70—C71—C72119.1 (2)
C27—N1—C31118.3 (2)N4—C72—C71122.9 (2)
C27—N1—Pd1126.13 (16)N2—C32—C33120.9 (2)
C31—N1—Pd1114.32 (15)N2—C32—C31116.12 (19)
C12—C2—C3118.74 (18)C33—C32—C31122.9 (2)
C12—C2—C1117.21 (17)O9—C41—O10121.52 (19)
C3—C2—C1113.48 (17)O9—C41—C37125.3 (2)
C12—C2—C9117.71 (18)O10—C41—C37112.93 (18)
C3—C2—C9117.24 (17)C66—C65—C64119.3 (2)
C1—C2—C957.94 (13)N3—C63—C64123.0 (2)
C36—N2—C32118.5 (2)O8—C24—C25105.62 (18)
C36—N2—Pd1125.78 (15)O3—C12—O4122.2 (2)
C32—N2—Pd1114.64 (15)O3—C12—C2125.5 (2)
C41—C37—C45118.37 (18)O4—C12—C2112.18 (18)
C41—C37—C38120.79 (17)O5—C16—O6122.45 (19)
C45—C37—C3861.55 (13)O5—C16—C3126.8 (2)
C41—C37—Pd2110.95 (13)O6—C16—C3110.69 (18)
C45—C37—Pd2122.92 (14)C4—C20—C21120.91 (18)
C38—C37—Pd2114.23 (13)C4—C20—C22118.68 (18)
C59—C40—C56117.24 (17)C21—C20—C22111.50 (18)
C59—C40—C39117.74 (17)C4—C20—C360.06 (13)
C56—C40—C3961.24 (13)C21—C20—C3117.99 (18)
C59—C40—Pd2111.72 (14)C22—C20—C3119.00 (18)
C56—C40—Pd2125.62 (14)O16—C60—C61107.75 (18)
C39—C40—Pd2113.78 (13)C35—C34—C33118.4 (2)
C5—C1—C9118.16 (18)C23—C4—C20117.36 (18)
C5—C1—C2118.82 (17)C23—C4—C3119.92 (17)
C9—C1—C261.56 (14)C20—C4—C361.77 (14)
C5—C1—Pd1110.33 (14)C23—C4—Pd1110.51 (14)
C9—C1—Pd1125.90 (15)C20—C4—Pd1125.21 (15)
C2—C1—Pd1113.54 (14)C3—C4—Pd1114.16 (14)
C16—O6—C17116.36 (17)C70—C69—C68119.8 (2)
N1—C31—C30121.3 (2)O4—C13—C14109.5 (2)
N1—C31—C32115.18 (19)O15—C59—O16121.31 (19)
C30—C31—C32123.6 (2)O15—C59—C40126.1 (2)
N4—C68—C69121.7 (2)O16—C59—C40112.53 (18)
N4—C68—C67115.79 (18)C65—C66—C67119.7 (2)
C69—C68—C67122.4 (2)N1—C27—C28123.1 (2)
C1—C9—C11119.12 (18)O12—C49—C50109.5 (2)
C1—C9—C10122.38 (19)C19—C18—C17127.5 (3)
C11—C9—C10109.89 (18)C34—C35—C36119.1 (2)
C1—C9—C260.50 (14)C65—C64—C63118.4 (2)
C11—C9—C2118.86 (18)C29—C28—C27118.7 (2)
C10—C9—C2118.47 (18)O14—C53—C54109.39 (19)
C37—C45—C46121.82 (18)N2—C36—C35122.8 (2)
C37—C45—C47118.45 (18)C62—C61—C60123.3 (3)
C46—C45—C47110.67 (18)O7—C23—O8121.41 (19)
C37—C45—C3860.25 (13)O7—C23—C4126.2 (2)
C46—C45—C38118.85 (18)O8—C23—C4112.23 (18)
C47—C45—C38118.68 (18)C28—C29—C30119.0 (2)
O1—C5—O2121.7 (2)C71—C70—C69118.5 (2)
O1—C5—C1126.4 (2)O6—C17—C18108.6 (2)
O2—C5—C1111.71 (18)C8—C7—C6123.9 (3)
C52—C39—C38117.18 (18)O2—C6—C7106.7 (2)
C52—C39—C40118.60 (17)C34—C33—C32120.3 (2)
C38—C39—C40113.57 (16)C15—C14—C13126.7 (3)
C52—C39—C56118.63 (18)C55—C54—C53127.3 (2)
C38—C39—C56117.45 (17)C26—C25—C24122.5 (3)
C40—C39—C5658.05 (13)C29—C30—C31119.6 (2)
C16—C3—C2116.23 (18)O10—C42—C43109.9 (2)
C16—C3—C4119.06 (17)C44—C43—C42126.5 (3)
C37—Pd2—N3—C6317.11 (19)C40—C39—C52—O1325.0 (3)
N4—Pd2—N3—C63173.26 (19)C56—C39—C52—O1342.1 (3)
C37—Pd2—N3—C67169.85 (15)C38—C39—C52—O1411.3 (3)
N4—Pd2—N3—C670.22 (14)C40—C39—C52—O14153.69 (18)
C40—Pd2—N4—C7217.99 (18)C56—C39—C52—O14139.21 (18)
N3—Pd2—N4—C72171.92 (18)C63—N3—C67—C660.6 (3)
C40—Pd2—N4—C68175.13 (14)Pd2—N3—C67—C66174.19 (16)
N3—Pd2—N4—C685.04 (14)C63—N3—C67—C68178.69 (19)
C1—Pd1—N1—C2718.3 (2)Pd2—N3—C67—C685.0 (2)
N2—Pd1—N1—C27173.18 (19)N4—C68—C67—N39.6 (3)
C1—Pd1—N1—C31174.97 (15)C69—C68—C67—N3167.4 (2)
N2—Pd1—N1—C316.49 (15)N4—C68—C67—C66169.6 (2)
C4—Pd1—N2—C3622.07 (19)C69—C68—C67—C6613.3 (3)
N1—Pd1—N2—C36169.29 (19)C49—O12—C48—O115.4 (3)
C4—Pd1—N2—C32169.85 (15)C49—O12—C48—C38171.67 (18)
N1—Pd1—N2—C321.21 (15)C39—C38—C48—O11164.0 (2)
C40—Pd2—C37—C41140.70 (16)C37—C38—C48—O1122.7 (3)
N3—Pd2—C37—C4148.80 (16)C45—C38—C48—O1144.2 (3)
C40—Pd2—C37—C4570.65 (17)C39—C38—C48—O1213.0 (3)
N3—Pd2—C37—C4599.85 (17)C37—C38—C48—O12154.35 (18)
C40—Pd2—C37—C380.03 (14)C45—C38—C48—O12138.78 (19)
N3—Pd2—C37—C38170.53 (14)C68—N4—C72—C710.5 (3)
C37—Pd2—C40—C59141.85 (16)Pd2—N4—C72—C71165.97 (17)
N4—Pd2—C40—C5947.71 (16)C70—C71—C72—N40.5 (3)
C37—Pd2—C40—C5665.10 (18)C36—N2—C32—C330.4 (3)
N4—Pd2—C40—C56105.34 (17)Pd1—N2—C32—C33169.39 (18)
C37—Pd2—C40—C395.56 (14)C36—N2—C32—C31177.21 (19)
N4—Pd2—C40—C39176.00 (13)Pd1—N2—C32—C318.2 (2)
C12—C2—C1—C51.2 (3)N1—C31—C32—N214.0 (3)
C3—C2—C1—C5143.19 (19)C30—C31—C32—N2165.5 (2)
C9—C2—C1—C5108.3 (2)N1—C31—C32—C33163.5 (2)
C12—C2—C1—C9107.2 (2)C30—C31—C32—C3317.0 (3)
C3—C2—C1—C9108.47 (19)C42—O10—C41—O90.5 (3)
C12—C2—C1—Pd1133.41 (17)C42—O10—C41—C37174.2 (2)
C3—C2—C1—Pd111.0 (2)C45—C37—C41—O942.0 (3)
C9—C2—C1—Pd1119.43 (16)C38—C37—C41—O9114.1 (2)
C4—Pd1—C1—C5141.59 (16)Pd2—C37—C41—O9108.2 (2)
N1—Pd1—C1—C548.97 (16)C45—C37—C41—O10143.42 (19)
C4—Pd1—C1—C965.61 (18)C38—C37—C41—O1071.4 (2)
N1—Pd1—C1—C9103.83 (18)Pd2—C37—C41—O1066.3 (2)
C4—Pd1—C1—C25.37 (14)C67—N3—C63—C643.4 (3)
N1—Pd1—C1—C2174.81 (14)Pd2—N3—C63—C64176.29 (18)
C27—N1—C31—C300.9 (3)C23—O8—C24—C25178.78 (19)
Pd1—N1—C31—C30166.90 (17)C13—O4—C12—O33.0 (3)
C27—N1—C31—C32179.55 (19)C13—O4—C12—C2173.7 (2)
Pd1—N1—C31—C3212.6 (2)C3—C2—C12—O3168.8 (2)
C72—N4—C68—C690.2 (3)C1—C2—C12—O326.3 (3)
Pd2—N4—C68—C69167.84 (17)C9—C2—C12—O339.8 (3)
C72—N4—C68—C67177.27 (18)C3—C2—C12—O47.7 (3)
Pd2—N4—C68—C679.2 (2)C1—C2—C12—O4150.19 (19)
C5—C1—C9—C11142.0 (2)C9—C2—C12—O4143.65 (19)
C2—C1—C9—C11108.6 (2)C17—O6—C16—O53.0 (3)
Pd1—C1—C9—C118.9 (3)C17—O6—C16—C3175.50 (19)
C5—C1—C9—C102.5 (3)C2—C3—C16—O5158.7 (2)
C2—C1—C9—C10106.8 (2)C4—C3—C16—O517.4 (3)
Pd1—C1—C9—C10153.45 (17)C20—C3—C16—O549.8 (3)
C5—C1—C9—C2109.4 (2)C2—C3—C16—O619.6 (3)
Pd1—C1—C9—C299.71 (18)C4—C3—C16—O6160.96 (18)
C12—C2—C9—C1106.3 (2)C20—C3—C16—O6131.86 (19)
C3—C2—C9—C1101.9 (2)C16—C3—C20—C4108.5 (2)
C12—C2—C9—C11144.7 (2)C2—C3—C20—C4100.9 (2)
C3—C2—C9—C117.2 (3)C16—C3—C20—C212.9 (3)
C1—C2—C9—C11109.1 (2)C2—C3—C20—C21147.70 (19)
C12—C2—C9—C106.9 (3)C4—C3—C20—C21111.4 (2)
C3—C2—C9—C10144.9 (2)C16—C3—C20—C22143.2 (2)
C1—C2—C9—C10113.1 (2)C2—C3—C20—C227.4 (3)
C41—C37—C45—C464.2 (3)C4—C3—C20—C22108.3 (2)
C38—C37—C45—C46107.4 (2)C59—O16—C60—C61176.45 (19)
Pd2—C37—C45—C46150.72 (17)C21—C20—C4—C234.4 (3)
C41—C37—C45—C47139.7 (2)C22—C20—C4—C23140.1 (2)
C38—C37—C45—C47108.6 (2)C3—C20—C4—C23111.1 (2)
Pd2—C37—C45—C476.8 (3)C21—C20—C4—C3106.6 (2)
C41—C37—C45—C38111.7 (2)C22—C20—C4—C3108.8 (2)
Pd2—C37—C45—C38101.85 (17)C21—C20—C4—Pd1152.43 (17)
C6—O2—C5—O112.2 (3)C22—C20—C4—Pd17.9 (3)
C6—O2—C5—C1172.79 (18)C3—C20—C4—Pd1100.93 (18)
C9—C1—C5—O145.8 (3)C16—C3—C4—C230.3 (3)
C2—C1—C5—O1117.0 (3)C2—C3—C4—C23142.02 (19)
Pd1—C1—C5—O1109.4 (2)C20—C3—C4—C23107.0 (2)
C9—C1—C5—O2139.44 (19)C16—C3—C4—C20106.7 (2)
C2—C1—C5—O268.2 (2)C2—C3—C4—C20110.94 (19)
Pd1—C1—C5—O265.4 (2)C16—C3—C4—Pd1134.82 (17)
C59—C40—C39—C520.1 (3)C2—C3—C4—Pd17.5 (2)
C56—C40—C39—C52107.6 (2)C20—C3—C4—Pd1118.46 (16)
Pd2—C40—C39—C52133.40 (16)C1—Pd1—C4—C23139.81 (16)
C59—C40—C39—C38143.76 (19)N2—Pd1—C4—C2351.13 (16)
C56—C40—C39—C38108.70 (19)C1—Pd1—C4—C2070.36 (18)
Pd2—C40—C39—C3810.3 (2)N2—Pd1—C4—C2098.70 (18)
C59—C40—C39—C56107.5 (2)C1—Pd1—C4—C31.10 (15)
Pd2—C40—C39—C56118.96 (16)N2—Pd1—C4—C3170.16 (14)
C12—C2—C3—C1684.6 (2)N4—C68—C69—C700.0 (3)
C1—C2—C3—C16131.65 (19)C67—C68—C69—C70176.8 (2)
C9—C2—C3—C1667.0 (2)C12—O4—C13—C14169.4 (2)
C12—C2—C3—C4132.0 (2)C60—O16—C59—O1518.2 (3)
C1—C2—C3—C411.8 (2)C60—O16—C59—C40164.71 (17)
C9—C2—C3—C476.5 (2)C56—C40—C59—O1545.0 (3)
C12—C2—C3—C2066.6 (3)C39—C40—C59—O15115.1 (2)
C1—C2—C3—C2077.2 (2)Pd2—C40—C59—O15110.5 (2)
C9—C2—C3—C20141.91 (19)C56—C40—C59—O16138.05 (19)
C52—C39—C38—C4883.1 (2)C39—C40—C59—O1668.0 (2)
C40—C39—C38—C48132.74 (19)Pd2—C40—C59—O1666.4 (2)
C56—C39—C38—C4867.8 (2)C64—C65—C66—C672.6 (3)
C52—C39—C38—C37133.97 (18)N3—C67—C66—C652.4 (3)
C40—C39—C38—C3710.2 (2)C68—C67—C66—C65178.4 (2)
C56—C39—C38—C3775.1 (2)C31—N1—C27—C280.5 (3)
C52—C39—C38—C4568.6 (2)Pd1—N1—C27—C28166.68 (18)
C40—C39—C38—C4575.6 (2)C48—O12—C49—C50171.2 (2)
C56—C39—C38—C45140.48 (18)C51—C50—C49—O126.1 (4)
C41—C37—C38—C480.4 (3)C33—C34—C35—C360.6 (4)
C45—C37—C38—C48107.4 (2)C66—C65—C64—C630.0 (4)
Pd2—C37—C38—C48136.86 (16)N3—C63—C64—C653.2 (4)
C41—C37—C38—C39142.22 (19)N1—C27—C28—C291.4 (4)
C45—C37—C38—C39109.95 (19)C52—O14—C53—C54179.3 (2)
Pd2—C37—C38—C395.8 (2)C32—N2—C36—C350.2 (3)
C41—C37—C38—C45107.8 (2)Pd1—N2—C36—C35167.50 (18)
Pd2—C37—C38—C45115.72 (16)C34—C35—C36—N20.7 (4)
C37—C45—C38—C48107.1 (2)O16—C60—C61—C62135.6 (3)
C46—C45—C38—C485.2 (3)C24—O8—C23—O715.7 (3)
C47—C45—C38—C48144.7 (2)C24—O8—C23—C4168.66 (18)
C37—C45—C38—C39101.5 (2)C20—C4—C23—O743.6 (3)
C46—C45—C38—C39146.23 (19)C3—C4—C23—O7115.1 (3)
C47—C45—C38—C396.7 (3)Pd1—C4—C23—O7108.9 (2)
C46—C45—C38—C37112.2 (2)C20—C4—C23—O8141.04 (19)
C47—C45—C38—C37108.2 (2)C3—C4—C23—O869.5 (2)
C59—C40—C56—C58144.26 (19)Pd1—C4—C23—O866.5 (2)
C39—C40—C56—C58107.4 (2)C27—C28—C29—C301.0 (4)
Pd2—C40—C56—C587.5 (3)C72—C71—C70—C690.3 (4)
C59—C40—C56—C570.3 (3)C68—C69—C70—C710.0 (4)
C39—C40—C56—C57108.6 (2)C16—O6—C17—C18177.0 (2)
Pd2—C40—C56—C57151.45 (17)C19—C18—C17—O60.8 (4)
C59—C40—C56—C39108.3 (2)C5—O2—C6—C7157.5 (2)
Pd2—C40—C56—C3999.93 (18)C8—C7—C6—O2126.1 (3)
C52—C39—C56—C40107.59 (19)C35—C34—C33—C320.0 (4)
C38—C39—C56—C40101.95 (19)N2—C32—C33—C340.4 (4)
C52—C39—C56—C58141.83 (19)C31—C32—C33—C34177.0 (2)
C38—C39—C56—C588.6 (3)O4—C13—C14—C155.3 (4)
C40—C39—C56—C58110.6 (2)O14—C53—C54—C553.6 (4)
C52—C39—C56—C574.2 (3)O8—C24—C25—C26116.9 (3)
C38—C39—C56—C57146.24 (19)C28—C29—C30—C310.3 (4)
C40—C39—C56—C57111.8 (2)N1—C31—C30—C291.3 (3)
C53—O14—C52—O132.0 (3)C32—C31—C30—C29179.2 (2)
C53—O14—C52—C39176.84 (18)C41—O10—C42—C43162.3 (2)
C38—C39—C52—O13167.4 (2)O10—C42—C43—C4419.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O30.962.222.916 (3)128
C11—H11C···O80.962.303.255 (3)173
C21—H21B···O50.962.263.016 (3)135
C22—H22C···O20.962.403.358 (3)176
C27—H27···O10.932.333.093 (3)139
C36—H36···O70.932.413.105 (3)132
C46—H46C···O110.962.282.982 (3)129
C47—H47B···O160.962.353.297 (3)171
C57—H57C···O130.962.252.979 (3)132
C58—H58B···O100.962.343.286 (3)168
C63—H63···O90.932.282.974 (3)131
C72—H72···O150.932.393.182 (3)143
C8—H8A···O13i0.932.573.346 (3)141
C19—H19B···O9ii0.932.533.397 (3)156
C24—H24B···O7iii0.972.583.483 (3)156
C60—H60A···O15iv0.972.463.392 (3)161
Symmetry codes: (i) x1, y, z+1; (ii) x+1, y, z; (iii) x, y1, z; (iv) x1, y+1, z+1.
(I205K) tetraallyl (2,2'-bipyridyl)-rac-3,3,7,7-tetramethyl-trans-5-palladatricyclo [4.1.0.02,4]heptane-1,2,4,6-tetracarboxylate top
Crystal data top
[Pd(C10H8N2)(C26H32O8)]Z = 2
Mr = 735.10F(000) = 760
Triclinic, P1Dx = 1.422 Mg m3
a = 8.9583 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3245 (18) ÅCell parameters from 155 reflections
c = 17.906 (3) Åθ = 3–23°
α = 83.438 (16)°µ = 0.59 mm1
β = 88.482 (14)°T = 205 K
γ = 72.118 (16)°Plate, yellow
V = 1717.4 (4) Å30.44 × 0.17 × 0.04 mm
Data collection top
SIEMENS SMART
diffractometer
10543 independent reflections
Radiation source: normal-focus sealed tube8751 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
ω scansθmax = 31.2°, θmin = 1.9°
Absorption correction: numerical (SHELXTL; sheldrick, 1996)
?
h = 1213
Tmin = 0.791, Tmax = 0.977k = 1516
31971 measured reflectionsl = 2426
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.31(Δ/σ)max = 0.001
10543 reflectionsΔρmax = 0.56 e Å3
451 parametersΔρmin = 0.55 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0020 (6)
Crystal data top
[Pd(C10H8N2)(C26H32O8)]γ = 72.118 (16)°
Mr = 735.10V = 1717.4 (4) Å3
Triclinic, P1Z = 2
a = 8.9583 (8) ÅMo Kα radiation
b = 11.3245 (18) ŵ = 0.59 mm1
c = 17.906 (3) ÅT = 205 K
α = 83.438 (16)°0.44 × 0.17 × 0.04 mm
β = 88.482 (14)°
Data collection top
SIEMENS SMART
diffractometer
10543 independent reflections
Absorption correction: numerical (SHELXTL; sheldrick, 1996)
?
8751 reflections with I > 2σ(I)
Tmin = 0.791, Tmax = 0.977Rint = 0.070
31971 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.31Δρmax = 0.56 e Å3
10543 reflectionsΔρmin = 0.55 e Å3
451 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pd0.180174 (18)0.431505 (14)0.343610 (8)0.02450 (6)
C140.5109 (4)0.2234 (3)0.04479 (17)0.0593 (8)
H140.59610.23570.01310.071*
N20.2411 (2)0.41538 (17)0.45833 (9)0.0296 (4)
C30.1596 (2)0.24489 (17)0.23259 (10)0.0225 (4)
C10.1684 (2)0.47267 (18)0.22952 (11)0.0266 (4)
O80.08206 (18)0.13876 (14)0.36380 (8)0.0340 (3)
O70.1232 (2)0.09300 (15)0.41946 (9)0.0398 (4)
C20.1733 (2)0.36538 (18)0.18448 (10)0.0240 (4)
O50.00261 (19)0.02805 (13)0.24253 (8)0.0354 (3)
C40.1721 (2)0.25793 (18)0.31740 (10)0.0240 (4)
O40.33138 (18)0.30129 (15)0.10504 (9)0.0367 (4)
O60.00686 (18)0.15138 (14)0.13504 (8)0.0343 (3)
N10.1505 (2)0.59423 (17)0.37945 (10)0.0322 (4)
C310.1715 (3)0.6044 (2)0.45389 (12)0.0319 (4)
C160.0508 (2)0.12942 (19)0.20628 (11)0.0266 (4)
C230.0733 (3)0.15511 (19)0.37106 (11)0.0285 (4)
C90.0308 (2)0.41691 (19)0.18144 (11)0.0274 (4)
C100.0035 (3)0.4858 (2)0.10819 (13)0.0374 (5)
H10A0.07130.53350.11810.056*
H10B0.09290.54090.08620.056*
H10C0.05390.42650.07400.056*
C320.2335 (3)0.5098 (2)0.49604 (12)0.0328 (5)
O10.2294 (2)0.69030 (15)0.18181 (10)0.0463 (4)
C50.2725 (3)0.6018 (2)0.20539 (12)0.0343 (5)
O20.4255 (2)0.61324 (16)0.21831 (10)0.0486 (5)
O30.3243 (2)0.49795 (16)0.08057 (9)0.0448 (4)
C200.3042 (2)0.2322 (2)0.27922 (11)0.0274 (4)
C220.4595 (3)0.3355 (2)0.26608 (14)0.0391 (5)
H22A0.52410.33470.30970.059*
H22B0.51200.32210.22320.059*
H22C0.44030.41470.25700.059*
C120.2811 (3)0.3971 (2)0.11803 (11)0.0309 (4)
C270.0933 (3)0.6772 (2)0.33839 (14)0.0416 (5)
H270.07620.66990.28740.050*
C280.0585 (3)0.7731 (2)0.36852 (16)0.0460 (6)
H280.02080.82970.33810.055*
C210.3325 (3)0.1066 (2)0.29257 (14)0.0412 (5)
H21A0.38590.10070.33940.062*
H21B0.23380.04150.29440.062*
H21C0.39570.09780.25240.062*
C170.1020 (3)0.0462 (2)0.10419 (14)0.0470 (6)
H17A0.05750.02210.10640.056*
H17B0.19870.01800.13330.056*
C110.1221 (3)0.3365 (2)0.21973 (13)0.0358 (5)
H11A0.18060.38910.23340.054*
H11B0.18260.28070.18590.054*
H11C0.09940.28910.26410.054*
C330.2856 (3)0.5180 (2)0.56984 (13)0.0465 (6)
H330.27450.58100.59620.056*
C130.4523 (4)0.3304 (3)0.04709 (16)0.0556 (8)
H13A0.40920.34980.00140.067*
H13B0.53790.40300.05780.067*
C360.3075 (3)0.3320 (2)0.49193 (13)0.0377 (5)
H360.31400.26740.46580.045*
C350.3667 (3)0.3387 (3)0.56397 (14)0.0491 (7)
H350.41460.28090.58520.059*
C300.1357 (3)0.6972 (2)0.48700 (14)0.0419 (6)
H300.14900.70160.53840.050*
C240.1832 (3)0.0201 (2)0.39897 (14)0.0453 (6)
H24A0.16700.04710.37530.054*0.596 (9)
H24B0.15720.00920.45120.054*0.596 (9)
H24C0.12660.04050.40540.054*0.404 (9)
H24D0.21730.02950.44770.054*0.404 (9)
C190.0732 (4)0.1883 (3)0.01334 (16)0.0655 (9)
H19A0.00230.25160.00790.079*
H19B0.10350.20150.06290.079*
C180.1348 (4)0.0841 (3)0.02535 (15)0.0564 (7)
H180.20940.02450.00120.068*
C290.0802 (3)0.7834 (2)0.44336 (16)0.0481 (6)
H290.05810.84730.46480.058*
C340.3538 (4)0.4314 (3)0.60340 (14)0.0543 (7)
H340.39050.43630.65240.065*
C150.4571 (4)0.1131 (3)0.08207 (19)0.0649 (8)
H15A0.37190.09550.11460.078*
H15B0.50380.05180.07620.078*
C80.8277 (6)0.7376 (5)0.1961 (3)0.0602 (16)0.613 (7)
H8A0.84190.80170.22620.072*0.613 (7)
H8B0.91200.71050.18530.072*0.613 (7)
C250.3401 (6)0.0164 (6)0.3921 (4)0.0579 (18)0.596 (9)
H250.37260.04620.34590.070*0.596 (9)
C260.4449 (8)0.0263 (8)0.4465 (5)0.108 (4)0.596 (9)
H26A0.41620.05660.49340.130*0.596 (9)
H26B0.54770.02610.43820.130*0.596 (9)
C25'0.3273 (10)0.0251 (10)0.3465 (7)0.069 (3)0.404 (9)
H25B0.30260.00610.29560.083*0.404 (9)
C26'0.4677 (12)0.0812 (8)0.3597 (11)0.114 (7)0.404 (9)
H26C0.50360.10420.40910.137*0.404 (9)
H26D0.53720.10040.32020.137*0.404 (9)
C60.5469 (5)0.7185 (4)0.1810 (3)0.0410 (11)*0.613 (7)
H6A0.50830.74590.13310.049*0.613 (7)
H6B0.57210.78730.21160.049*0.613 (7)
C70.6881 (6)0.6851 (5)0.1685 (3)0.0501 (13)*0.613 (7)
H7A0.67900.62130.13860.060*0.613 (7)
C7'0.6837 (10)0.7529 (8)0.2061 (5)0.061 (3)*0.387 (7)
H7'A0.75710.82460.22010.074*0.387 (7)
C6'0.5195 (9)0.7501 (8)0.2082 (5)0.055 (2)*0.387 (7)
H6'A0.50070.79170.24980.066*0.387 (7)
H6'B0.49160.79100.16180.066*0.387 (7)
C8'0.7357 (16)0.6726 (12)0.1881 (6)0.078 (3)*0.387 (7)
H8'A0.66780.59880.17360.093*0.387 (7)
H8'B0.84320.68500.18900.093*0.387 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd0.03211 (9)0.02283 (8)0.01928 (8)0.00983 (6)0.00041 (5)0.00133 (5)
C140.0556 (17)0.079 (2)0.0516 (17)0.0286 (16)0.0151 (14)0.0154 (16)
N20.0331 (9)0.0298 (9)0.0242 (8)0.0075 (7)0.0010 (7)0.0020 (7)
C30.0247 (9)0.0225 (9)0.0203 (8)0.0079 (7)0.0011 (7)0.0002 (7)
C10.0343 (10)0.0239 (9)0.0208 (9)0.0090 (8)0.0014 (8)0.0013 (7)
O80.0373 (8)0.0299 (8)0.0319 (8)0.0085 (6)0.0108 (6)0.0069 (6)
O70.0531 (10)0.0351 (8)0.0280 (8)0.0133 (7)0.0024 (7)0.0087 (7)
C20.0284 (9)0.0243 (9)0.0178 (8)0.0071 (7)0.0020 (7)0.0019 (7)
O50.0481 (9)0.0224 (7)0.0312 (8)0.0055 (6)0.0019 (7)0.0008 (6)
C40.0296 (9)0.0231 (9)0.0196 (8)0.0095 (7)0.0006 (7)0.0002 (7)
O40.0403 (8)0.0363 (8)0.0322 (8)0.0096 (7)0.0153 (7)0.0012 (7)
O60.0425 (8)0.0292 (8)0.0253 (7)0.0025 (6)0.0062 (6)0.0036 (6)
N10.0408 (10)0.0276 (9)0.0287 (9)0.0109 (8)0.0035 (8)0.0033 (7)
C310.0329 (10)0.0289 (10)0.0298 (10)0.0020 (8)0.0061 (8)0.0052 (8)
C160.0288 (10)0.0273 (10)0.0235 (9)0.0086 (8)0.0037 (8)0.0015 (8)
C230.0416 (11)0.0242 (9)0.0200 (9)0.0112 (8)0.0038 (8)0.0001 (7)
C90.0317 (10)0.0261 (10)0.0246 (9)0.0109 (8)0.0007 (8)0.0017 (8)
C100.0471 (13)0.0375 (12)0.0298 (11)0.0195 (10)0.0073 (10)0.0040 (9)
C320.0350 (11)0.0314 (11)0.0263 (10)0.0015 (9)0.0022 (8)0.0038 (8)
O10.0684 (12)0.0269 (8)0.0412 (9)0.0140 (8)0.0025 (8)0.0042 (7)
C50.0490 (13)0.0277 (11)0.0226 (10)0.0077 (9)0.0012 (9)0.0016 (8)
O20.0427 (9)0.0355 (9)0.0516 (11)0.0048 (7)0.0054 (8)0.0131 (8)
O30.0574 (11)0.0384 (9)0.0337 (9)0.0122 (8)0.0209 (8)0.0137 (7)
C200.0291 (10)0.0315 (10)0.0235 (9)0.0124 (8)0.0002 (8)0.0011 (8)
C220.0274 (10)0.0479 (14)0.0405 (13)0.0100 (10)0.0043 (9)0.0038 (10)
C120.0329 (10)0.0338 (11)0.0228 (9)0.0057 (8)0.0033 (8)0.0014 (8)
C270.0567 (15)0.0348 (12)0.0380 (12)0.0215 (11)0.0013 (11)0.0018 (10)
C280.0551 (15)0.0316 (12)0.0537 (16)0.0177 (11)0.0129 (12)0.0010 (11)
C210.0479 (14)0.0437 (13)0.0410 (13)0.0278 (11)0.0017 (11)0.0034 (11)
C170.0537 (15)0.0378 (13)0.0404 (13)0.0015 (11)0.0095 (11)0.0125 (10)
C110.0286 (10)0.0400 (12)0.0390 (12)0.0129 (9)0.0013 (9)0.0016 (10)
C330.0609 (16)0.0425 (13)0.0295 (11)0.0041 (12)0.0060 (11)0.0115 (10)
C130.0619 (17)0.0596 (18)0.0462 (15)0.0191 (14)0.0309 (13)0.0005 (13)
C360.0425 (12)0.0349 (12)0.0328 (11)0.0097 (10)0.0067 (9)0.0013 (9)
C350.0518 (15)0.0457 (15)0.0404 (14)0.0076 (12)0.0134 (11)0.0094 (11)
C300.0514 (14)0.0348 (12)0.0387 (12)0.0080 (10)0.0080 (11)0.0137 (10)
C240.0512 (14)0.0365 (13)0.0370 (13)0.0016 (11)0.0091 (11)0.0111 (10)
C190.099 (3)0.066 (2)0.0381 (15)0.0349 (19)0.0187 (16)0.0067 (14)
C180.0686 (19)0.0582 (18)0.0410 (14)0.0144 (15)0.0161 (13)0.0170 (13)
C290.0560 (15)0.0296 (12)0.0608 (17)0.0126 (11)0.0150 (13)0.0113 (11)
C340.0673 (18)0.0511 (16)0.0307 (12)0.0000 (13)0.0152 (12)0.0025 (11)
C150.070 (2)0.074 (2)0.065 (2)0.0372 (18)0.0035 (16)0.0236 (18)
C80.053 (3)0.039 (2)0.075 (4)0.003 (2)0.003 (2)0.004 (2)
C250.037 (2)0.064 (4)0.065 (4)0.018 (2)0.008 (3)0.030 (3)
C260.054 (4)0.132 (7)0.131 (8)0.044 (4)0.044 (4)0.075 (6)
C25'0.046 (4)0.062 (5)0.072 (7)0.007 (4)0.002 (4)0.033 (5)
C26'0.067 (6)0.041 (5)0.223 (19)0.019 (4)0.007 (8)0.036 (7)
Geometric parameters (Å, º) top
Pd—C12.0503 (19)C31—C301.386 (3)
Pd—C42.052 (2)C31—C321.477 (3)
Pd—N12.1114 (18)C9—C101.522 (3)
Pd—N22.1136 (17)C9—C111.522 (3)
C14—C151.302 (5)C32—C331.393 (3)
C14—C131.466 (4)O1—C51.210 (3)
N2—C361.343 (3)C5—O21.353 (3)
N2—C321.348 (3)O2—C61.453 (4)
C3—C161.489 (3)O2—C6'1.512 (8)
C3—C21.501 (3)O3—C121.213 (3)
C3—C41.540 (3)C20—C211.511 (3)
C3—C201.557 (3)C20—C221.521 (3)
C1—C51.495 (3)C27—C281.385 (3)
C1—C91.499 (3)C28—C291.362 (4)
C1—C21.545 (3)C17—C181.477 (4)
O8—C231.351 (3)C33—C341.381 (4)
O8—C241.453 (3)C36—C351.383 (3)
O7—C231.216 (2)C35—C341.365 (4)
C2—C121.492 (3)C30—C291.383 (4)
C2—C91.555 (3)C24—C251.396 (6)
O5—C161.211 (2)C24—C25'1.565 (10)
C4—C231.490 (3)C19—C181.269 (4)
C4—C201.501 (3)C8—C71.319 (8)
O4—C121.341 (3)C25—C261.314 (8)
O4—C131.456 (3)C25'—C26'1.237 (12)
O6—C161.343 (2)C6—C71.457 (7)
O6—C171.443 (3)C7'—C8'1.218 (14)
N1—C271.343 (3)C7'—C6'1.463 (12)
N1—C311.354 (3)
C1—Pd—C484.20 (8)O7—C23—O8121.32 (19)
C1—Pd—N199.77 (8)O7—C23—C4125.1 (2)
C4—Pd—N1170.14 (7)O8—C23—C4113.55 (17)
C1—Pd—N2167.86 (7)C1—C9—C10122.30 (18)
C4—Pd—N2100.09 (7)C1—C9—C11118.63 (17)
N1—Pd—N277.87 (7)C10—C9—C11109.95 (18)
C15—C14—C13127.4 (3)C1—C9—C260.74 (13)
C36—N2—C32118.65 (19)C10—C9—C2118.88 (17)
C36—N2—Pd125.52 (16)C11—C9—C2118.82 (17)
C32—N2—Pd114.98 (15)N2—C32—C33121.1 (2)
C16—C3—C2116.75 (16)N2—C32—C31116.13 (19)
C16—C3—C4119.32 (16)C33—C32—C31122.7 (2)
C2—C3—C4113.59 (16)O1—C5—O2121.9 (2)
C16—C3—C20117.49 (17)O1—C5—C1125.9 (2)
C2—C3—C20118.71 (16)O2—C5—C1112.01 (19)
C4—C3—C2057.96 (12)C5—O2—C6120.1 (2)
C5—C1—C9118.58 (17)C5—O2—C6'109.0 (4)
C5—C1—C2118.82 (17)C4—C20—C21121.65 (18)
C9—C1—C261.42 (13)C4—C20—C22119.22 (18)
C5—C1—Pd110.33 (14)C21—C20—C22110.06 (19)
C9—C1—Pd125.45 (14)C4—C20—C360.45 (13)
C2—C1—Pd113.66 (13)C21—C20—C3119.41 (19)
C23—O8—C24114.98 (18)C22—C20—C3118.38 (17)
C12—C2—C3117.10 (17)O3—C12—O4122.52 (19)
C12—C2—C1117.78 (16)O3—C12—C2125.4 (2)
C3—C2—C1113.73 (15)O4—C12—C2112.06 (17)
C12—C2—C9118.57 (17)N1—C27—C28123.0 (2)
C3—C2—C9118.25 (16)C29—C28—C27119.1 (2)
C1—C2—C957.84 (13)O6—C17—C18109.2 (2)
C23—C4—C20116.81 (17)C34—C33—C32119.3 (2)
C23—C4—C3119.08 (17)O4—C13—C14109.7 (2)
C20—C4—C361.59 (13)N2—C36—C35122.5 (2)
C23—C4—Pd112.68 (13)C34—C35—C36119.0 (3)
C20—C4—Pd123.47 (14)C29—C30—C31119.8 (2)
C3—C4—Pd113.98 (12)C25—C24—O8110.1 (3)
C12—O4—C13115.01 (18)O8—C24—C25'107.9 (3)
C16—O6—C17115.75 (17)C19—C18—C17127.7 (3)
C27—N1—C31117.8 (2)C28—C29—C30118.9 (2)
C27—N1—Pd126.33 (16)C35—C34—C33119.3 (2)
C31—N1—Pd115.16 (15)C26—C25—C24124.3 (5)
N1—C31—C30121.4 (2)C26'—C25'—C24132.5 (11)
N1—C31—C32115.24 (19)O2—C6—C7111.2 (4)
C30—C31—C32123.4 (2)C8—C7—C6125.5 (5)
O5—C16—O6122.39 (19)C8'—C7'—C6'127.7 (11)
O5—C16—C3126.64 (19)C7'—C6'—O2105.4 (7)
O6—C16—C3110.96 (16)
C4—Pd—N2—C3620.15 (19)C12—C2—C9—C106.4 (3)
N1—Pd—N2—C36169.69 (19)C3—C2—C9—C10145.38 (19)
C4—Pd—N2—C32170.63 (15)C1—C2—C9—C10113.0 (2)
N1—Pd—N2—C320.47 (15)C12—C2—C9—C11144.9 (2)
C4—Pd—C1—C5140.93 (16)C3—C2—C9—C116.9 (3)
N1—Pd—C1—C548.19 (16)C1—C2—C9—C11108.6 (2)
C4—Pd—C1—C966.20 (18)C36—N2—C32—C333.4 (3)
N1—Pd—C1—C9104.69 (18)Pd—N2—C32—C33173.38 (18)
C4—Pd—C1—C24.58 (14)C36—N2—C32—C31174.96 (19)
N1—Pd—C1—C2175.47 (14)Pd—N2—C32—C315.0 (2)
C16—C3—C2—C1282.2 (2)N1—C31—C32—N28.9 (3)
C4—C3—C2—C12132.87 (18)C30—C31—C32—N2170.8 (2)
C20—C3—C2—C1267.8 (2)N1—C31—C32—C33169.4 (2)
C16—C3—C2—C1134.97 (18)C30—C31—C32—C3310.9 (3)
C4—C3—C2—C110.0 (2)C9—C1—C5—O144.0 (3)
C20—C3—C2—C175.1 (2)C2—C1—C5—O1115.2 (3)
C16—C3—C2—C970.0 (2)Pd—C1—C5—O1111.0 (2)
C4—C3—C2—C974.9 (2)C9—C1—C5—O2140.9 (2)
C20—C3—C2—C9140.01 (18)C2—C1—C5—O269.7 (2)
C5—C1—C2—C120.9 (3)Pd—C1—C5—O264.1 (2)
C9—C1—C2—C12107.90 (19)O1—C5—O2—C621.6 (4)
Pd—C1—C2—C12133.26 (16)C1—C5—O2—C6163.1 (3)
C5—C1—C2—C3141.68 (19)O1—C5—O2—C6'7.1 (5)
C9—C1—C2—C3109.53 (18)C1—C5—O2—C6'168.2 (4)
Pd—C1—C2—C39.3 (2)C23—C4—C20—C212.0 (3)
C5—C1—C2—C9108.8 (2)C3—C4—C20—C21108.3 (2)
Pd—C1—C2—C9118.85 (15)Pd—C4—C20—C21150.40 (17)
C16—C3—C4—C230.8 (3)C23—C4—C20—C22141.78 (19)
C2—C3—C4—C23143.19 (18)C3—C4—C20—C22108.0 (2)
C20—C3—C4—C23106.6 (2)Pd—C4—C20—C226.7 (3)
C16—C3—C4—C20105.9 (2)C23—C4—C20—C3110.23 (19)
C2—C3—C4—C20110.19 (18)Pd—C4—C20—C3101.32 (16)
C16—C3—C4—Pd137.68 (15)C16—C3—C20—C4109.00 (18)
C2—C3—C4—Pd6.3 (2)C2—C3—C20—C4101.28 (19)
C20—C3—C4—Pd116.46 (15)C16—C3—C20—C212.9 (3)
C1—Pd—C4—C23140.53 (15)C2—C3—C20—C21146.83 (19)
N2—Pd—C4—C2350.93 (15)C4—C3—C20—C21111.9 (2)
C1—Pd—C4—C2069.87 (16)C16—C3—C20—C22141.65 (19)
N2—Pd—C4—C2098.66 (16)C2—C3—C20—C228.1 (3)
C1—Pd—C4—C30.85 (14)C4—C3—C20—C22109.4 (2)
N2—Pd—C4—C3169.38 (13)C13—O4—C12—O35.3 (3)
C1—Pd—N1—C2717.4 (2)C13—O4—C12—C2172.5 (2)
N2—Pd—N1—C27174.7 (2)C3—C2—C12—O3167.9 (2)
C1—Pd—N1—C31172.32 (15)C1—C2—C12—O326.6 (3)
N2—Pd—N1—C314.45 (15)C9—C2—C12—O340.0 (3)
C27—N1—C31—C300.2 (3)C3—C2—C12—O49.8 (3)
Pd—N1—C31—C30171.33 (17)C1—C2—C12—O4151.16 (18)
C27—N1—C31—C32179.5 (2)C9—C2—C12—O4142.30 (19)
Pd—N1—C31—C328.3 (2)C31—N1—C27—C281.4 (4)
C17—O6—C16—O50.0 (3)Pd—N1—C27—C28171.48 (19)
C17—O6—C16—C3178.59 (19)N1—C27—C28—C291.2 (4)
C2—C3—C16—O5166.1 (2)C16—O6—C17—C18178.3 (2)
C4—C3—C16—O523.2 (3)N2—C32—C33—C343.5 (4)
C20—C3—C16—O543.6 (3)C31—C32—C33—C34174.7 (2)
C2—C3—C16—O612.5 (2)C12—O4—C13—C14173.0 (2)
C4—C3—C16—O6155.35 (17)C15—C14—C13—O46.4 (5)
C20—C3—C16—O6137.82 (17)C32—N2—C36—C350.8 (3)
C24—O8—C23—O719.3 (3)Pd—N2—C36—C35169.62 (18)
C24—O8—C23—C4163.38 (18)N2—C36—C35—C341.7 (4)
C20—C4—C23—O746.5 (3)N1—C31—C30—C291.3 (3)
C3—C4—C23—O7117.3 (2)C32—C31—C30—C29179.1 (2)
Pd—C4—C23—O7105.2 (2)C23—O8—C24—C25176.3 (4)
C20—C4—C23—O8136.22 (18)C23—O8—C24—C25'141.9 (6)
C3—C4—C23—O865.4 (2)O6—C17—C18—C194.2 (5)
Pd—C4—C23—O872.01 (19)C27—C28—C29—C300.3 (4)
C5—C1—C9—C101.7 (3)C31—C30—C29—C281.5 (4)
C2—C1—C9—C10107.5 (2)C36—C35—C34—C331.6 (4)
Pd—C1—C9—C10152.53 (17)C32—C33—C34—C350.9 (4)
C5—C1—C9—C11142.0 (2)O8—C24—C25—C26136.6 (7)
C2—C1—C9—C11108.9 (2)O8—C24—C25'—C26'143.8 (12)
Pd—C1—C9—C118.9 (3)C5—O2—C6—C7149.7 (3)
C5—C1—C9—C2109.2 (2)O2—C6—C7—C8119.3 (6)
Pd—C1—C9—C299.97 (17)C8'—C7'—C6'—O224.8 (14)
C12—C2—C9—C1106.53 (19)C5—O2—C6'—C7'167.5 (5)
C3—C2—C9—C1101.64 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O30.962.282.950 (3)126
C11—H11C···O80.962.363.305 (3)168
C21—H21B···O50.962.222.959 (3)133
C22—H22C···O20.962.323.268 (3)170
C27—H27···O10.932.313.057 (3)137
C36—H36···O70.932.403.111 (3)134
C8—H8A···O5i0.932.573.370 (6)144
C24—H24B···O7ii0.962.523.446 (3)161
Symmetry codes: (i) x1, y+1, z; (ii) x, y, z+1.

Experimental details

(I143K)(I205K)
Crystal data
Chemical formula[Pd(C10H8N2)(C26H32O8)][Pd(C10H8N2)(C26H32O8)]
Mr735.10735.10
Crystal system, space groupTriclinic, P1Triclinic, P1
Temperature (K)143205
a, b, c (Å)9.0197 (6), 17.918 (2), 21.375 (3)8.9583 (8), 11.3245 (18), 17.906 (3)
α, β, γ (°)95.641 (12), 97.375 (11), 93.083 (9)83.438 (16), 88.482 (14), 72.118 (16)
V3)3401.7 (7)1717.4 (4)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.600.59
Crystal size (mm)0.44 × 0.17 × 0.040.44 × 0.17 × 0.04
Data collection
DiffractometerSIEMENS SMART
diffractometer
SIEMENS SMART
diffractometer
Absorption correctionNumerical (SHELXTL; Sheldrick, 1996)Numerical (SHELXTL; Sheldrick, 1996)
Tmin, Tmax0.817, 0.9770.791, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
64204, 22046, 16183 31971, 10543, 8751
Rint0.0590.070
(sin θ/λ)max1)0.7500.729
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.101, 1.21 0.042, 0.101, 1.31
No. of reflections2204610543
No. of parameters856451
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.610.56, 0.55

Computer programs: SMART (Siemens, 1995), SMART, SAINT (Siemens, 1995), SHELXS96 (Sheldrick, 1996), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Sheldrick, 1996), CIF in SHELXL97.

Hydrogen-bond geometry (Å, º) for (I143K) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O30.962.222.916 (3)128
C11—H11C···O80.962.303.255 (3)173
C21—H21B···O50.962.263.016 (3)135
C22—H22C···O20.962.403.358 (3)176
C27—H27···O10.932.333.093 (3)139
C36—H36···O70.932.413.105 (3)132
C46—H46C···O110.962.282.982 (3)129
C47—H47B···O160.962.353.297 (3)171
C57—H57C···O130.962.252.979 (3)132
C58—H58B···O100.962.343.286 (3)168
C63—H63···O90.932.282.974 (3)131
C72—H72···O150.932.393.182 (3)143
C8—H8A···O13i0.932.573.346 (3)141
C19—H19B···O9ii0.932.533.397 (3)156
C24—H24B···O7iii0.972.583.483 (3)156
C60—H60A···O15iv0.972.463.392 (3)161
Symmetry codes: (i) x1, y, z+1; (ii) x+1, y, z; (iii) x, y1, z; (iv) x1, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (I205K) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O30.962.282.950 (3)126
C11—H11C···O80.962.363.305 (3)168
C21—H21B···O50.962.222.959 (3)133
C22—H22C···O20.962.323.268 (3)170
C27—H27···O10.932.313.057 (3)137
C36—H36···O70.932.403.111 (3)134
C8—H8A···O5i0.932.573.370 (6)144
C24—H24B···O7ii0.962.523.446 (3)161
Symmetry codes: (i) x1, y+1, z; (ii) x, y, z+1.
 

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