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The crystal structure of the title compound, (2,2′-bipyridyl-κ
2N,N′)(tetraallyl 3,3,3′,3′-tetramethyl-1,1′-bicyclopropane-1,1′,2,2′-tetracarboxylato-κ
2C2,
C2′)palladium(II), [Pd(C
26H
32O
8)(C
10H
8N
2)], 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
CCDC references: 147634; 147635
(I) was prepared as described by Hashmi et al. (1999). Suitable crystals were obtained by crystallization from hexane/dichloromethane at 277 K.
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: H—C(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.
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.
(I143K) tetraallyl (2,2'-bipyridyl)-rac-3,3,7,7-tetramethyl-
trans-5-palladatricyclo [4.1.0.0
2,4]heptane-1,2,4,6-tetracarboxylate
top
Crystal data top
[Pd(C10H8N2)(C26H32O8)] | Z = 4 |
Mr = 735.10 | F(000) = 1520 |
Triclinic, P1 | Dx = 1.435 Mg m−3 |
a = 9.0197 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.918 (2) Å | Cell parameters from 276 reflections |
c = 21.375 (3) Å | θ = 3–23° |
α = 95.641 (12)° | µ = 0.60 mm−1 |
β = 97.375 (11)° | T = 143 K |
γ = 93.083 (9)° | Plate, yellow |
V = 3401.7 (7) Å3 | 0.44 × 0.17 × 0.04 mm |
Data collection top
SIEMENS SMART diffractometer | 22046 independent reflections |
Radiation source: sealed tube | 16183 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans | θmax = 32.2°, θmin = 1.4° |
Absorption correction: numerical (SHELXTL; sheldrick, 1996) ? | h = −13→13 |
Tmin = 0.817, Tmax = 0.977 | k = −26→24 |
64204 measured reflections | l = −32→31 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-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 reflections | Δρmax = 0.56 e Å−3 |
856 parameters | Δρmin = −0.61 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00053 (14) |
Crystal data top
[Pd(C10H8N2)(C26H32O8)] | γ = 93.083 (9)° |
Mr = 735.10 | V = 3401.7 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.0197 (6) Å | Mo Kα radiation |
b = 17.918 (2) Å | µ = 0.60 mm−1 |
c = 21.375 (3) Å | T = 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 = 0.977 | Rint = 0.059 |
64204 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.21 | Δρmax = 0.56 e Å−3 |
22046 reflections | Δρmin = −0.61 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Pd1 | −0.017816 (18) | −0.339624 (9) | 0.210874 (7) | 0.01716 (5) | |
Pd2 | −0.552762 (17) | 0.346667 (8) | 0.286322 (7) | 0.01484 (5) | |
C50 | −0.1130 (3) | 0.04246 (15) | 0.38086 (13) | 0.0349 (6) | |
H50 | −0.0370 | 0.0110 | 0.3734 | 0.042* | |
O5 | 0.02199 (18) | −0.23621 (9) | 0.01307 (7) | 0.0240 (3) | |
O13 | −0.47474 (18) | 0.24308 (8) | 0.48821 (7) | 0.0233 (3) | |
O12 | −0.33265 (17) | 0.10344 (8) | 0.34456 (7) | 0.0223 (3) | |
O14 | −0.55946 (18) | 0.13684 (8) | 0.42685 (7) | 0.0215 (3) | |
O11 | −0.44905 (19) | 0.08494 (9) | 0.24432 (8) | 0.0277 (4) | |
O9 | −0.6658 (2) | 0.18947 (9) | 0.15352 (7) | 0.0287 (4) | |
O8 | 0.12367 (17) | −0.36104 (9) | 0.07704 (7) | 0.0221 (3) | |
O2 | −0.17079 (18) | −0.21406 (9) | 0.29772 (7) | 0.0261 (4) | |
O15 | −0.38639 (17) | 0.41565 (8) | 0.45781 (7) | 0.0231 (3) | |
N3 | −0.6933 (2) | 0.38044 (10) | 0.20910 (8) | 0.0203 (4) | |
O4 | −0.20322 (19) | −0.09745 (9) | 0.14295 (7) | 0.0259 (4) | |
N4 | −0.4981 (2) | 0.46486 (10) | 0.29504 (8) | 0.0175 (4) | |
O16 | −0.62108 (17) | 0.36342 (8) | 0.43559 (7) | 0.0202 (3) | |
O1 | 0.06365 (19) | −0.18332 (9) | 0.34619 (7) | 0.0285 (4) | |
O10 | −0.42252 (19) | 0.22548 (9) | 0.18319 (7) | 0.0277 (4) | |
N1 | 0.0819 (2) | −0.38040 (11) | 0.29515 (8) | 0.0221 (4) | |
C2 | −0.0231 (2) | −0.17923 (12) | 0.17924 (9) | 0.0174 (4) | |
O7 | −0.10524 (18) | −0.41115 (9) | 0.03601 (7) | 0.0259 (4) | |
O3 | −0.1032 (2) | −0.07676 (9) | 0.24523 (7) | 0.0288 (4) | |
N2 | −0.0975 (2) | −0.45329 (10) | 0.19685 (9) | 0.0206 (4) | |
C37 | −0.5840 (2) | 0.23238 (11) | 0.26334 (9) | 0.0159 (4) | |
C40 | −0.4446 (2) | 0.31820 (11) | 0.37041 (9) | 0.0156 (4) | |
C1 | 0.0245 (2) | −0.22624 (12) | 0.23439 (10) | 0.0177 (4) | |
O6 | 0.05328 (19) | −0.12615 (9) | 0.07475 (7) | 0.0248 (3) | |
C31 | 0.0612 (3) | −0.45555 (13) | 0.29584 (10) | 0.0230 (5) | |
C68 | −0.5654 (2) | 0.50048 (12) | 0.24730 (10) | 0.0189 (4) | |
C9 | 0.1428 (2) | −0.17759 (12) | 0.21125 (10) | 0.0189 (4) | |
C45 | −0.6890 (2) | 0.18336 (12) | 0.29370 (10) | 0.0182 (4) | |
C5 | −0.0200 (3) | −0.20354 (12) | 0.29793 (10) | 0.0220 (5) | |
C39 | −0.4546 (2) | 0.23290 (11) | 0.37639 (9) | 0.0153 (4) | |
C3 | −0.0637 (2) | −0.22579 (11) | 0.11613 (10) | 0.0168 (4) | |
C38 | −0.5170 (2) | 0.18606 (11) | 0.31568 (9) | 0.0153 (4) | |
C56 | −0.3022 (2) | 0.27818 (12) | 0.37795 (10) | 0.0176 (4) | |
C52 | −0.4944 (2) | 0.20678 (12) | 0.43631 (10) | 0.0177 (4) | |
C67 | −0.6827 (2) | 0.45501 (12) | 0.20271 (10) | 0.0186 (4) | |
C10 | 0.2131 (3) | −0.10501 (12) | 0.24916 (11) | 0.0255 (5) | |
H10A | 0.2995 | −0.1158 | 0.2771 | 0.038* | |
H10B | 0.1414 | −0.0829 | 0.2736 | 0.038* | |
H10C | 0.2425 | −0.0706 | 0.2206 | 0.038* | |
C48 | −0.4343 (2) | 0.11937 (12) | 0.29645 (10) | 0.0192 (4) | |
C46 | −0.7672 (3) | 0.11107 (12) | 0.25873 (11) | 0.0243 (5) | |
H46A | −0.8593 | 0.1221 | 0.2347 | 0.037* | |
H46B | −0.7882 | 0.0769 | 0.2888 | 0.037* | |
H46C | −0.7035 | 0.0886 | 0.2306 | 0.037* | |
C11 | 0.2575 (2) | −0.21468 (13) | 0.17425 (11) | 0.0244 (5) | |
H11A | 0.3372 | −0.2302 | 0.2033 | 0.037* | |
H11B | 0.2975 | −0.1795 | 0.1487 | 0.037* | |
H11C | 0.2101 | −0.2577 | 0.1474 | 0.037* | |
C71 | −0.3377 (3) | 0.57628 (13) | 0.32926 (11) | 0.0267 (5) | |
H71 | −0.2595 | 0.6007 | 0.3578 | 0.032* | |
C72 | −0.3866 (3) | 0.50296 (12) | 0.33514 (10) | 0.0220 (5) | |
H72 | −0.3401 | 0.4791 | 0.3683 | 0.026* | |
C58 | −0.2159 (2) | 0.26374 (13) | 0.32205 (10) | 0.0222 (5) | |
H58A | −0.1439 | 0.3051 | 0.3218 | 0.033* | |
H58B | −0.2842 | 0.2586 | 0.2833 | 0.033* | |
H58C | −0.1650 | 0.2183 | 0.3256 | 0.033* | |
C32 | −0.0524 (3) | −0.49371 (12) | 0.24523 (11) | 0.0243 (5) | |
C41 | −0.5656 (3) | 0.21133 (12) | 0.19543 (10) | 0.0205 (4) | |
C65 | −0.8821 (3) | 0.43972 (14) | 0.11654 (11) | 0.0283 (5) | |
H65 | −0.9438 | 0.4595 | 0.0849 | 0.034* | |
C63 | −0.8000 (3) | 0.33690 (13) | 0.17059 (11) | 0.0256 (5) | |
H63 | −0.8114 | 0.2862 | 0.1763 | 0.031* | |
C24 | 0.1834 (2) | −0.40113 (13) | 0.02438 (11) | 0.0238 (5) | |
H24A | 0.1502 | −0.3807 | −0.0150 | 0.029* | |
H24B | 0.1509 | −0.4541 | 0.0201 | 0.029* | |
C12 | −0.1089 (2) | −0.11250 (12) | 0.19369 (10) | 0.0212 (4) | |
C47 | −0.7885 (2) | 0.22102 (13) | 0.33801 (11) | 0.0239 (5) | |
H47A | −0.8758 | 0.2368 | 0.3135 | 0.036* | |
H47B | −0.7340 | 0.2640 | 0.3625 | 0.036* | |
H47C | −0.8184 | 0.1861 | 0.3660 | 0.036* | |
C57 | −0.1932 (3) | 0.28997 (13) | 0.43928 (11) | 0.0240 (5) | |
H57A | −0.1316 | 0.3355 | 0.4400 | 0.036* | |
H57B | −0.1310 | 0.2482 | 0.4417 | 0.036* | |
H57C | −0.2484 | 0.2936 | 0.4749 | 0.036* | |
C16 | 0.0054 (2) | −0.19909 (12) | 0.06213 (10) | 0.0195 (4) | |
C20 | −0.2190 (2) | −0.27098 (12) | 0.10127 (10) | 0.0191 (4) | |
C21 | −0.2940 (3) | −0.28175 (14) | 0.03293 (10) | 0.0256 (5) | |
H21A | −0.3523 | −0.3290 | 0.0252 | 0.038* | |
H21B | −0.2189 | −0.2814 | 0.0050 | 0.038* | |
H21C | −0.3583 | −0.2417 | 0.0254 | 0.038* | |
C60 | −0.6515 (3) | 0.39672 (13) | 0.49713 (10) | 0.0230 (5) | |
H60A | −0.6281 | 0.4506 | 0.5015 | 0.028* | |
H60B | −0.5904 | 0.3755 | 0.5308 | 0.028* | |
C34 | −0.2262 (3) | −0.59726 (15) | 0.20007 (13) | 0.0372 (6) | |
H34 | −0.2687 | −0.6455 | 0.2011 | 0.045* | |
C4 | −0.0807 (2) | −0.31049 (12) | 0.12147 (10) | 0.0176 (4) | |
C69 | −0.5217 (3) | 0.57390 (13) | 0.23925 (11) | 0.0274 (5) | |
H69 | −0.5698 | 0.5972 | 0.2060 | 0.033* | |
C13 | −0.3012 (3) | −0.03797 (15) | 0.15626 (13) | 0.0384 (7) | |
H13A | −0.2432 | 0.0100 | 0.1649 | 0.046* | |
H13B | −0.3482 | −0.0468 | 0.1935 | 0.046* | |
C59 | −0.4755 (2) | 0.36980 (12) | 0.42563 (10) | 0.0182 (4) | |
C66 | −0.7781 (3) | 0.48577 (13) | 0.15745 (10) | 0.0239 (5) | |
H66 | −0.7718 | 0.5373 | 0.1548 | 0.029* | |
C27 | 0.1829 (3) | −0.34216 (14) | 0.34013 (11) | 0.0273 (5) | |
H27 | 0.1979 | −0.2905 | 0.3396 | 0.033* | |
C49 | −0.2331 (3) | 0.04637 (14) | 0.32732 (12) | 0.0314 (6) | |
H49A | −0.1893 | 0.0585 | 0.2901 | 0.038* | |
H49B | −0.2890 | −0.0020 | 0.3171 | 0.038* | |
C18 | 0.1690 (3) | −0.01357 (16) | 0.04842 (15) | 0.0431 (7) | |
H18 | 0.2220 | 0.0127 | 0.0221 | 0.052* | |
C35 | −0.2721 (3) | −0.55546 (14) | 0.15128 (13) | 0.0330 (6) | |
H35 | −0.3471 | −0.5749 | 0.1189 | 0.040* | |
C64 | −0.8939 (3) | 0.36398 (14) | 0.12287 (11) | 0.0280 (5) | |
H64 | −0.9634 | 0.3318 | 0.0957 | 0.034* | |
C28 | 0.2655 (3) | −0.37592 (15) | 0.38720 (11) | 0.0303 (5) | |
H28 | 0.3329 | −0.3474 | 0.4181 | 0.036* | |
C53 | −0.6093 (3) | 0.10828 (13) | 0.48209 (11) | 0.0285 (5) | |
H53A | −0.6827 | 0.1401 | 0.4980 | 0.034* | |
H53B | −0.5250 | 0.1086 | 0.5153 | 0.034* | |
C36 | −0.2050 (3) | −0.48408 (13) | 0.15106 (12) | 0.0263 (5) | |
H36 | −0.2359 | −0.4564 | 0.1177 | 0.032* | |
C61 | −0.8121 (3) | 0.38028 (16) | 0.50108 (12) | 0.0337 (6) | |
H61 | −0.8539 | 0.3319 | 0.4875 | 0.040* | |
C23 | −0.0274 (2) | −0.36465 (12) | 0.07303 (10) | 0.0197 (4) | |
C29 | 0.2462 (3) | −0.45242 (15) | 0.38742 (12) | 0.0346 (6) | |
H29 | 0.3015 | −0.4767 | 0.4182 | 0.042* | |
C22 | −0.3331 (3) | −0.25940 (14) | 0.14744 (11) | 0.0245 (5) | |
H22A | −0.3951 | −0.3049 | 0.1462 | 0.037* | |
H22B | −0.3945 | −0.2196 | 0.1357 | 0.037* | |
H22C | −0.2817 | −0.2464 | 0.1896 | 0.037* | |
C70 | −0.4064 (3) | 0.61240 (13) | 0.28069 (11) | 0.0312 (6) | |
H70 | −0.3759 | 0.6617 | 0.2758 | 0.037* | |
C19 | 0.1359 (4) | 0.02453 (16) | 0.09808 (14) | 0.0486 (8) | |
H19A | 0.0831 | 0.0012 | 0.1262 | 0.058* | |
H19B | 0.1648 | 0.0756 | 0.1060 | 0.058* | |
C17 | 0.1327 (3) | −0.09460 (14) | 0.02819 (12) | 0.0337 (6) | |
H17A | 0.0711 | −0.1012 | −0.0129 | 0.040* | |
H17B | 0.2241 | −0.1199 | 0.0245 | 0.040* | |
C7 | −0.3896 (3) | −0.17404 (14) | 0.33666 (12) | 0.0318 (6) | |
H7 | −0.4150 | −0.1448 | 0.3038 | 0.038* | |
C6 | −0.2281 (3) | −0.18535 (15) | 0.35501 (11) | 0.0325 (6) | |
H6A | −0.1744 | −0.1382 | 0.3729 | 0.039* | |
H6B | −0.2166 | −0.2210 | 0.3864 | 0.039* | |
C33 | −0.1154 (3) | −0.56587 (13) | 0.24736 (12) | 0.0335 (6) | |
H33 | −0.0827 | −0.5931 | 0.2808 | 0.040* | |
C14 | −0.4173 (3) | −0.03609 (16) | 0.10108 (13) | 0.0407 (7) | |
H14 | −0.4915 | −0.0027 | 0.1059 | 0.049* | |
C15 | −0.4265 (3) | −0.07680 (16) | 0.04595 (13) | 0.0411 (7) | |
H15A | −0.3551 | −0.1111 | 0.0388 | 0.049* | |
H15B | −0.5045 | −0.0714 | 0.0141 | 0.049* | |
C55 | −0.6852 (3) | −0.00957 (15) | 0.41025 (14) | 0.0408 (7) | |
H55A | −0.6460 | 0.0103 | 0.3768 | 0.049* | |
H55B | −0.7304 | −0.0581 | 0.4046 | 0.049* | |
C54 | −0.6770 (3) | 0.03033 (14) | 0.46466 (13) | 0.0360 (6) | |
H54 | −0.7180 | 0.0077 | 0.4964 | 0.043* | |
C25 | 0.3475 (3) | −0.39059 (16) | 0.03988 (12) | 0.0326 (6) | |
H25A | 0.3928 | −0.3422 | 0.0434 | 0.039* | |
C51 | −0.1028 (3) | 0.07899 (16) | 0.43796 (14) | 0.0411 (7) | |
H51A | −0.1759 | 0.1112 | 0.4478 | 0.049* | |
H51B | −0.0224 | 0.0726 | 0.4684 | 0.049* | |
C62 | −0.8977 (3) | 0.42987 (19) | 0.52260 (14) | 0.0511 (9) | |
H62A | −0.8586 | 0.4786 | 0.5365 | 0.061* | |
H62B | −0.9982 | 0.4167 | 0.5241 | 0.061* | |
C30 | 0.1433 (3) | −0.49290 (14) | 0.34122 (11) | 0.0320 (6) | |
H30 | 0.1290 | −0.5448 | 0.3405 | 0.038* | |
C44 | −0.1396 (4) | 0.19133 (19) | 0.15457 (17) | 0.0554 (9) | |
H44A | −0.1640 | 0.1831 | 0.1944 | 0.066* | |
H44B | −0.0412 | 0.1885 | 0.1463 | 0.066* | |
C8 | −0.4976 (3) | −0.20279 (16) | 0.36398 (13) | 0.0414 (7) | |
H8A | −0.4755 | −0.2323 | 0.3970 | 0.050* | |
H8B | −0.5965 | −0.1938 | 0.3504 | 0.050* | |
C26 | 0.4323 (3) | −0.44696 (19) | 0.04893 (14) | 0.0492 (8) | |
H26A | 0.3890 | −0.4957 | 0.0456 | 0.059* | |
H26B | 0.5357 | −0.4381 | 0.0586 | 0.059* | |
C42 | −0.4024 (4) | 0.21290 (18) | 0.11694 (12) | 0.0455 (8) | |
H42A | −0.4393 | 0.2544 | 0.0948 | 0.055* | |
H42B | −0.4593 | 0.1671 | 0.0976 | 0.055* | |
C43 | −0.2413 (4) | 0.20645 (17) | 0.11121 (15) | 0.0483 (8) | |
H43 | −0.2114 | 0.2142 | 0.0722 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd1 | 0.01947 (9) | 0.01368 (8) | 0.01753 (8) | 0.00030 (6) | −0.00052 (6) | 0.00197 (6) |
Pd2 | 0.01687 (8) | 0.01167 (8) | 0.01484 (8) | 0.00044 (6) | −0.00138 (6) | 0.00056 (6) |
C50 | 0.0320 (14) | 0.0297 (14) | 0.0446 (16) | 0.0110 (11) | 0.0028 (12) | 0.0108 (12) |
O5 | 0.0299 (9) | 0.0239 (8) | 0.0178 (8) | 0.0011 (7) | 0.0055 (7) | −0.0019 (6) |
O13 | 0.0351 (9) | 0.0169 (8) | 0.0168 (7) | −0.0009 (7) | 0.0014 (7) | 0.0009 (6) |
O12 | 0.0275 (8) | 0.0181 (8) | 0.0222 (8) | 0.0109 (7) | 0.0028 (6) | 0.0016 (6) |
O14 | 0.0298 (9) | 0.0161 (7) | 0.0183 (7) | −0.0039 (6) | 0.0044 (6) | 0.0019 (6) |
O11 | 0.0354 (10) | 0.0222 (8) | 0.0236 (8) | 0.0070 (7) | 0.0025 (7) | −0.0079 (7) |
O9 | 0.0383 (10) | 0.0256 (9) | 0.0184 (8) | −0.0031 (8) | −0.0037 (7) | −0.0030 (7) |
O8 | 0.0210 (8) | 0.0214 (8) | 0.0220 (8) | 0.0049 (6) | 0.0004 (6) | −0.0063 (6) |
O2 | 0.0286 (9) | 0.0315 (9) | 0.0172 (8) | −0.0008 (7) | 0.0057 (7) | −0.0035 (7) |
O15 | 0.0252 (8) | 0.0185 (8) | 0.0226 (8) | −0.0029 (7) | −0.0014 (6) | −0.0041 (6) |
N3 | 0.0236 (10) | 0.0174 (9) | 0.0189 (9) | 0.0033 (8) | −0.0023 (7) | 0.0025 (7) |
O4 | 0.0330 (9) | 0.0251 (9) | 0.0199 (8) | 0.0142 (7) | 0.0006 (7) | 0.0007 (7) |
N4 | 0.0188 (9) | 0.0166 (9) | 0.0170 (8) | 0.0001 (7) | 0.0029 (7) | 0.0012 (7) |
O16 | 0.0205 (8) | 0.0204 (8) | 0.0177 (7) | 0.0022 (6) | 0.0010 (6) | −0.0059 (6) |
O1 | 0.0330 (9) | 0.0313 (9) | 0.0185 (8) | 0.0030 (8) | −0.0041 (7) | −0.0020 (7) |
O10 | 0.0334 (10) | 0.0307 (9) | 0.0177 (8) | −0.0042 (7) | 0.0073 (7) | −0.0056 (7) |
N1 | 0.0258 (10) | 0.0217 (10) | 0.0191 (9) | 0.0038 (8) | 0.0014 (8) | 0.0045 (8) |
C2 | 0.0223 (11) | 0.0149 (10) | 0.0150 (10) | 0.0042 (8) | 0.0018 (8) | 0.0004 (8) |
O7 | 0.0258 (9) | 0.0223 (8) | 0.0260 (8) | −0.0023 (7) | −0.0002 (7) | −0.0079 (7) |
O3 | 0.0391 (10) | 0.0244 (9) | 0.0214 (8) | 0.0123 (8) | 0.0005 (7) | −0.0051 (7) |
N2 | 0.0215 (9) | 0.0157 (9) | 0.0245 (9) | 0.0004 (7) | 0.0037 (8) | 0.0017 (7) |
C37 | 0.0206 (10) | 0.0113 (9) | 0.0147 (9) | −0.0001 (8) | −0.0003 (8) | 0.0001 (8) |
C40 | 0.0188 (10) | 0.0129 (9) | 0.0137 (9) | −0.0006 (8) | −0.0016 (8) | −0.0008 (8) |
C1 | 0.0202 (11) | 0.0148 (10) | 0.0170 (10) | 0.0016 (8) | −0.0010 (8) | 0.0009 (8) |
O6 | 0.0353 (9) | 0.0170 (8) | 0.0236 (8) | −0.0006 (7) | 0.0095 (7) | 0.0031 (6) |
C31 | 0.0307 (12) | 0.0210 (11) | 0.0198 (11) | 0.0061 (10) | 0.0088 (9) | 0.0045 (9) |
C68 | 0.0229 (11) | 0.0181 (10) | 0.0161 (10) | 0.0021 (9) | 0.0047 (8) | 0.0000 (8) |
C9 | 0.0202 (11) | 0.0157 (10) | 0.0192 (10) | 0.0007 (8) | −0.0014 (8) | −0.0009 (8) |
C45 | 0.0201 (11) | 0.0149 (10) | 0.0182 (10) | −0.0010 (8) | 0.0005 (8) | −0.0014 (8) |
C5 | 0.0285 (12) | 0.0161 (10) | 0.0208 (11) | 0.0014 (9) | 0.0017 (9) | 0.0011 (9) |
C39 | 0.0162 (10) | 0.0130 (9) | 0.0163 (9) | 0.0028 (8) | 0.0008 (8) | 0.0006 (8) |
C3 | 0.0184 (10) | 0.0147 (10) | 0.0171 (10) | 0.0031 (8) | 0.0010 (8) | 0.0011 (8) |
C38 | 0.0186 (10) | 0.0116 (9) | 0.0148 (9) | 0.0013 (8) | 0.0003 (8) | −0.0015 (8) |
C56 | 0.0172 (10) | 0.0142 (10) | 0.0203 (10) | −0.0003 (8) | 0.0000 (8) | 0.0006 (8) |
C52 | 0.0188 (10) | 0.0167 (10) | 0.0178 (10) | 0.0038 (8) | 0.0016 (8) | 0.0023 (8) |
C67 | 0.0223 (11) | 0.0177 (10) | 0.0164 (10) | 0.0047 (9) | 0.0038 (8) | 0.0016 (8) |
C10 | 0.0283 (12) | 0.0176 (11) | 0.0281 (12) | −0.0012 (9) | −0.0009 (10) | −0.0024 (9) |
C48 | 0.0212 (11) | 0.0146 (10) | 0.0216 (11) | 0.0013 (8) | 0.0029 (9) | 0.0014 (8) |
C46 | 0.0256 (12) | 0.0198 (11) | 0.0250 (12) | −0.0053 (9) | −0.0008 (9) | −0.0014 (9) |
C11 | 0.0175 (11) | 0.0233 (12) | 0.0304 (12) | −0.0004 (9) | 0.0010 (9) | −0.0034 (10) |
C71 | 0.0304 (13) | 0.0221 (12) | 0.0254 (12) | −0.0076 (10) | 0.0031 (10) | −0.0027 (10) |
C72 | 0.0233 (11) | 0.0197 (11) | 0.0221 (11) | −0.0011 (9) | 0.0004 (9) | 0.0020 (9) |
C58 | 0.0190 (11) | 0.0222 (11) | 0.0258 (11) | 0.0005 (9) | 0.0042 (9) | 0.0043 (9) |
C32 | 0.0321 (13) | 0.0161 (11) | 0.0269 (12) | 0.0029 (9) | 0.0111 (10) | 0.0025 (9) |
C41 | 0.0314 (12) | 0.0121 (10) | 0.0169 (10) | 0.0004 (9) | 0.0017 (9) | −0.0006 (8) |
C65 | 0.0288 (13) | 0.0350 (14) | 0.0215 (11) | 0.0097 (11) | −0.0014 (9) | 0.0075 (10) |
C63 | 0.0274 (12) | 0.0178 (11) | 0.0284 (12) | 0.0009 (9) | −0.0071 (10) | 0.0012 (9) |
C24 | 0.0213 (11) | 0.0238 (12) | 0.0242 (11) | 0.0021 (9) | 0.0010 (9) | −0.0056 (9) |
C12 | 0.0230 (11) | 0.0189 (11) | 0.0222 (11) | 0.0039 (9) | 0.0034 (9) | 0.0033 (9) |
C47 | 0.0169 (11) | 0.0248 (12) | 0.0291 (12) | −0.0022 (9) | 0.0039 (9) | −0.0017 (10) |
C57 | 0.0219 (11) | 0.0214 (11) | 0.0257 (12) | 0.0006 (9) | −0.0066 (9) | 0.0007 (9) |
C16 | 0.0193 (11) | 0.0194 (11) | 0.0200 (10) | 0.0033 (9) | 0.0002 (8) | 0.0045 (9) |
C20 | 0.0184 (10) | 0.0187 (11) | 0.0190 (10) | 0.0008 (8) | 0.0000 (8) | −0.0006 (8) |
C21 | 0.0216 (11) | 0.0299 (13) | 0.0233 (11) | 0.0021 (10) | −0.0013 (9) | −0.0008 (10) |
C60 | 0.0293 (12) | 0.0218 (11) | 0.0163 (10) | 0.0029 (9) | 0.0021 (9) | −0.0058 (9) |
C34 | 0.0477 (17) | 0.0220 (13) | 0.0440 (16) | −0.0067 (12) | 0.0182 (13) | 0.0031 (11) |
C4 | 0.0188 (10) | 0.0148 (10) | 0.0183 (10) | −0.0004 (8) | −0.0001 (8) | 0.0011 (8) |
C69 | 0.0411 (14) | 0.0173 (11) | 0.0242 (12) | 0.0012 (10) | 0.0041 (10) | 0.0052 (9) |
C13 | 0.0472 (16) | 0.0350 (15) | 0.0335 (14) | 0.0282 (13) | 0.0007 (12) | −0.0011 (12) |
C59 | 0.0226 (11) | 0.0148 (10) | 0.0168 (10) | 0.0029 (9) | 0.0003 (8) | 0.0025 (8) |
C66 | 0.0301 (12) | 0.0204 (11) | 0.0218 (11) | 0.0081 (10) | 0.0012 (9) | 0.0051 (9) |
C27 | 0.0284 (13) | 0.0266 (13) | 0.0254 (12) | 0.0032 (10) | −0.0026 (10) | 0.0022 (10) |
C49 | 0.0366 (14) | 0.0247 (13) | 0.0348 (14) | 0.0155 (11) | 0.0082 (11) | 0.0004 (11) |
C18 | 0.0514 (18) | 0.0305 (15) | 0.0505 (18) | −0.0074 (13) | 0.0160 (15) | 0.0125 (13) |
C35 | 0.0283 (13) | 0.0262 (13) | 0.0417 (15) | −0.0086 (11) | 0.0056 (11) | −0.0057 (11) |
C64 | 0.0264 (12) | 0.0293 (13) | 0.0244 (12) | 0.0016 (10) | −0.0071 (10) | −0.0023 (10) |
C28 | 0.0306 (13) | 0.0384 (15) | 0.0217 (12) | 0.0086 (11) | 0.0000 (10) | 0.0030 (10) |
C53 | 0.0404 (15) | 0.0248 (12) | 0.0223 (11) | −0.0033 (11) | 0.0107 (10) | 0.0063 (10) |
C36 | 0.0246 (12) | 0.0212 (12) | 0.0325 (13) | −0.0003 (10) | 0.0013 (10) | 0.0034 (10) |
C61 | 0.0285 (13) | 0.0393 (15) | 0.0295 (13) | −0.0061 (11) | 0.0051 (11) | −0.0115 (11) |
C23 | 0.0212 (11) | 0.0175 (10) | 0.0194 (10) | 0.0020 (9) | −0.0013 (8) | 0.0017 (8) |
C29 | 0.0435 (16) | 0.0415 (16) | 0.0224 (12) | 0.0178 (13) | 0.0047 (11) | 0.0128 (11) |
C22 | 0.0205 (11) | 0.0302 (13) | 0.0223 (11) | −0.0001 (10) | 0.0029 (9) | 0.0011 (10) |
C70 | 0.0471 (16) | 0.0163 (11) | 0.0297 (13) | −0.0073 (11) | 0.0080 (11) | 0.0016 (10) |
C19 | 0.068 (2) | 0.0296 (15) | 0.0422 (17) | −0.0154 (15) | −0.0051 (15) | 0.0009 (13) |
C17 | 0.0441 (16) | 0.0284 (13) | 0.0328 (13) | 0.0005 (12) | 0.0188 (12) | 0.0079 (11) |
C7 | 0.0402 (15) | 0.0294 (13) | 0.0261 (12) | 0.0031 (11) | 0.0091 (11) | −0.0016 (10) |
C6 | 0.0392 (15) | 0.0362 (15) | 0.0214 (12) | −0.0009 (12) | 0.0092 (11) | −0.0050 (11) |
C33 | 0.0538 (17) | 0.0183 (12) | 0.0310 (13) | −0.0002 (11) | 0.0133 (12) | 0.0068 (10) |
C14 | 0.0419 (16) | 0.0414 (16) | 0.0412 (16) | 0.0219 (13) | 0.0020 (13) | 0.0098 (13) |
C15 | 0.0423 (16) | 0.0402 (16) | 0.0401 (16) | 0.0097 (13) | −0.0047 (13) | 0.0113 (13) |
C55 | 0.0534 (18) | 0.0241 (13) | 0.0427 (16) | −0.0083 (13) | 0.0002 (14) | 0.0073 (12) |
C54 | 0.0463 (17) | 0.0263 (13) | 0.0377 (15) | −0.0059 (12) | 0.0111 (13) | 0.0115 (11) |
C25 | 0.0237 (12) | 0.0380 (15) | 0.0332 (14) | 0.0018 (11) | 0.0001 (10) | −0.0057 (11) |
C51 | 0.0386 (16) | 0.0400 (16) | 0.0454 (17) | 0.0067 (13) | −0.0008 (13) | 0.0135 (14) |
C62 | 0.0242 (14) | 0.074 (2) | 0.0479 (18) | 0.0009 (14) | 0.0017 (13) | −0.0246 (17) |
C30 | 0.0474 (16) | 0.0250 (13) | 0.0280 (13) | 0.0106 (12) | 0.0114 (12) | 0.0111 (10) |
C44 | 0.056 (2) | 0.057 (2) | 0.055 (2) | 0.0069 (17) | 0.0232 (18) | −0.0059 (17) |
C8 | 0.0450 (17) | 0.0475 (18) | 0.0306 (14) | −0.0053 (14) | 0.0097 (12) | −0.0025 (13) |
C26 | 0.0297 (15) | 0.065 (2) | 0.0548 (19) | 0.0159 (15) | 0.0063 (13) | 0.0056 (16) |
C42 | 0.0553 (19) | 0.058 (2) | 0.0215 (13) | −0.0083 (15) | 0.0159 (13) | −0.0098 (13) |
C43 | 0.069 (2) | 0.0387 (17) | 0.0391 (17) | −0.0086 (16) | 0.0296 (16) | −0.0098 (13) |
Geometric parameters (Å, º) top
Pd1—C1 | 2.048 (2) | O6—C16 | 1.345 (3) |
Pd1—C4 | 2.048 (2) | O6—C17 | 1.440 (3) |
Pd1—N2 | 2.1028 (18) | C31—C30 | 1.391 (3) |
Pd1—N1 | 2.1217 (18) | C31—C32 | 1.477 (3) |
Pd2—C37 | 2.054 (2) | C68—C69 | 1.386 (3) |
Pd2—C40 | 2.056 (2) | C68—C67 | 1.479 (3) |
Pd2—N3 | 2.1070 (18) | C9—C11 | 1.522 (3) |
Pd2—N4 | 2.1331 (18) | C9—C10 | 1.524 (3) |
C50—C51 | 1.317 (4) | C45—C46 | 1.520 (3) |
C50—C49 | 1.481 (4) | C45—C47 | 1.522 (3) |
O5—C16 | 1.216 (2) | C45—C38 | 1.559 (3) |
O13—C52 | 1.217 (2) | C39—C52 | 1.485 (3) |
O12—C48 | 1.350 (3) | C39—C38 | 1.501 (3) |
O12—C49 | 1.449 (3) | C39—C56 | 1.553 (3) |
O14—C52 | 1.340 (2) | C3—C16 | 1.487 (3) |
O14—C53 | 1.445 (3) | C3—C4 | 1.534 (3) |
O11—C48 | 1.207 (3) | C3—C20 | 1.560 (3) |
O9—C41 | 1.207 (3) | C38—C48 | 1.494 (3) |
O8—C23 | 1.352 (3) | C56—C58 | 1.517 (3) |
O8—C24 | 1.453 (3) | C56—C57 | 1.524 (3) |
O2—C5 | 1.363 (3) | C67—C66 | 1.387 (3) |
O2—C6 | 1.449 (3) | C71—C70 | 1.375 (4) |
O15—C59 | 1.212 (3) | C71—C72 | 1.386 (3) |
N3—C63 | 1.343 (3) | C32—C33 | 1.391 (3) |
N3—C67 | 1.356 (3) | C65—C66 | 1.375 (3) |
O4—C12 | 1.348 (3) | C65—C64 | 1.377 (3) |
O4—C13 | 1.450 (3) | C63—C64 | 1.383 (3) |
N4—C72 | 1.342 (3) | C24—C25 | 1.472 (3) |
N4—C68 | 1.352 (3) | C20—C4 | 1.504 (3) |
O16—C59 | 1.357 (3) | C20—C21 | 1.518 (3) |
O16—C60 | 1.455 (2) | C20—C22 | 1.523 (3) |
O1—C5 | 1.209 (3) | C60—C61 | 1.477 (3) |
O10—C41 | 1.365 (3) | C34—C35 | 1.377 (4) |
O10—C42 | 1.448 (3) | C34—C33 | 1.380 (4) |
N1—C27 | 1.342 (3) | C4—C23 | 1.492 (3) |
N1—C31 | 1.351 (3) | C69—C70 | 1.382 (3) |
C2—C12 | 1.488 (3) | C13—C14 | 1.478 (4) |
C2—C3 | 1.506 (3) | C27—C28 | 1.382 (3) |
C2—C1 | 1.545 (3) | C18—C19 | 1.282 (4) |
C2—C9 | 1.561 (3) | C18—C17 | 1.480 (4) |
O7—C23 | 1.216 (3) | C35—C36 | 1.386 (3) |
O3—C12 | 1.212 (3) | C28—C29 | 1.373 (4) |
N2—C36 | 1.340 (3) | C53—C54 | 1.487 (3) |
N2—C32 | 1.353 (3) | C61—C62 | 1.297 (4) |
C37—C41 | 1.496 (3) | C29—C30 | 1.384 (4) |
C37—C45 | 1.506 (3) | C7—C8 | 1.306 (4) |
C37—C38 | 1.539 (3) | C7—C6 | 1.488 (4) |
C40—C59 | 1.491 (3) | C14—C15 | 1.314 (4) |
C40—C56 | 1.503 (3) | C55—C54 | 1.295 (4) |
C40—C39 | 1.545 (3) | C25—C26 | 1.314 (4) |
C1—C5 | 1.490 (3) | C44—C43 | 1.277 (5) |
C1—C9 | 1.505 (3) | C42—C43 | 1.484 (4) |
| | | |
C1—Pd1—C4 | 84.24 (8) | C2—C3—C4 | 113.42 (17) |
C1—Pd1—N2 | 168.62 (8) | C16—C3—C20 | 118.02 (18) |
C4—Pd1—N2 | 99.22 (8) | C2—C3—C20 | 119.23 (17) |
C1—Pd1—N1 | 100.46 (8) | C4—C3—C20 | 58.17 (13) |
C4—Pd1—N1 | 168.54 (8) | C48—C38—C39 | 117.10 (18) |
N2—Pd1—N1 | 78.21 (7) | C48—C38—C37 | 117.95 (17) |
C37—Pd2—C40 | 83.88 (8) | C39—C38—C37 | 113.61 (16) |
C37—Pd2—N3 | 98.56 (8) | C48—C38—C45 | 118.15 (17) |
C40—Pd2—N3 | 170.27 (7) | C39—C38—C45 | 118.48 (17) |
C37—Pd2—N4 | 169.19 (7) | C37—C38—C45 | 58.19 (13) |
C40—Pd2—N4 | 101.36 (7) | C40—C56—C58 | 120.05 (18) |
N3—Pd2—N4 | 77.86 (7) | C40—C56—C57 | 121.55 (18) |
C51—C50—C49 | 126.7 (2) | C58—C56—C57 | 109.55 (18) |
C48—O12—C49 | 114.73 (17) | C40—C56—C39 | 60.72 (13) |
C52—O14—C53 | 115.45 (16) | C58—C56—C39 | 118.09 (17) |
C23—O8—C24 | 115.52 (16) | C57—C56—C39 | 119.55 (18) |
C5—O2—C6 | 116.15 (18) | O13—C52—O14 | 122.39 (19) |
C63—N3—C67 | 118.11 (19) | O13—C52—C39 | 125.9 (2) |
C63—N3—Pd2 | 126.17 (15) | O14—C52—C39 | 111.66 (17) |
C67—N3—Pd2 | 115.37 (14) | N3—C67—C66 | 121.3 (2) |
C12—O4—C13 | 114.34 (17) | N3—C67—C68 | 115.78 (19) |
C72—N4—C68 | 117.89 (19) | C66—C67—C68 | 122.9 (2) |
C72—N4—Pd2 | 126.41 (15) | O11—C48—O12 | 122.82 (19) |
C68—N4—Pd2 | 114.46 (14) | O11—C48—C38 | 125.8 (2) |
C59—O16—C60 | 115.29 (16) | O12—C48—C38 | 111.27 (17) |
C41—O10—C42 | 114.86 (19) | C70—C71—C72 | 119.1 (2) |
C27—N1—C31 | 118.3 (2) | N4—C72—C71 | 122.9 (2) |
C27—N1—Pd1 | 126.13 (16) | N2—C32—C33 | 120.9 (2) |
C31—N1—Pd1 | 114.32 (15) | N2—C32—C31 | 116.12 (19) |
C12—C2—C3 | 118.74 (18) | C33—C32—C31 | 122.9 (2) |
C12—C2—C1 | 117.21 (17) | O9—C41—O10 | 121.52 (19) |
C3—C2—C1 | 113.48 (17) | O9—C41—C37 | 125.3 (2) |
C12—C2—C9 | 117.71 (18) | O10—C41—C37 | 112.93 (18) |
C3—C2—C9 | 117.24 (17) | C66—C65—C64 | 119.3 (2) |
C1—C2—C9 | 57.94 (13) | N3—C63—C64 | 123.0 (2) |
C36—N2—C32 | 118.5 (2) | O8—C24—C25 | 105.62 (18) |
C36—N2—Pd1 | 125.78 (15) | O3—C12—O4 | 122.2 (2) |
C32—N2—Pd1 | 114.64 (15) | O3—C12—C2 | 125.5 (2) |
C41—C37—C45 | 118.37 (18) | O4—C12—C2 | 112.18 (18) |
C41—C37—C38 | 120.79 (17) | O5—C16—O6 | 122.45 (19) |
C45—C37—C38 | 61.55 (13) | O5—C16—C3 | 126.8 (2) |
C41—C37—Pd2 | 110.95 (13) | O6—C16—C3 | 110.69 (18) |
C45—C37—Pd2 | 122.92 (14) | C4—C20—C21 | 120.91 (18) |
C38—C37—Pd2 | 114.23 (13) | C4—C20—C22 | 118.68 (18) |
C59—C40—C56 | 117.24 (17) | C21—C20—C22 | 111.50 (18) |
C59—C40—C39 | 117.74 (17) | C4—C20—C3 | 60.06 (13) |
C56—C40—C39 | 61.24 (13) | C21—C20—C3 | 117.99 (18) |
C59—C40—Pd2 | 111.72 (14) | C22—C20—C3 | 119.00 (18) |
C56—C40—Pd2 | 125.62 (14) | O16—C60—C61 | 107.75 (18) |
C39—C40—Pd2 | 113.78 (13) | C35—C34—C33 | 118.4 (2) |
C5—C1—C9 | 118.16 (18) | C23—C4—C20 | 117.36 (18) |
C5—C1—C2 | 118.82 (17) | C23—C4—C3 | 119.92 (17) |
C9—C1—C2 | 61.56 (14) | C20—C4—C3 | 61.77 (14) |
C5—C1—Pd1 | 110.33 (14) | C23—C4—Pd1 | 110.51 (14) |
C9—C1—Pd1 | 125.90 (15) | C20—C4—Pd1 | 125.21 (15) |
C2—C1—Pd1 | 113.54 (14) | C3—C4—Pd1 | 114.16 (14) |
C16—O6—C17 | 116.36 (17) | C70—C69—C68 | 119.8 (2) |
N1—C31—C30 | 121.3 (2) | O4—C13—C14 | 109.5 (2) |
N1—C31—C32 | 115.18 (19) | O15—C59—O16 | 121.31 (19) |
C30—C31—C32 | 123.6 (2) | O15—C59—C40 | 126.1 (2) |
N4—C68—C69 | 121.7 (2) | O16—C59—C40 | 112.53 (18) |
N4—C68—C67 | 115.79 (18) | C65—C66—C67 | 119.7 (2) |
C69—C68—C67 | 122.4 (2) | N1—C27—C28 | 123.1 (2) |
C1—C9—C11 | 119.12 (18) | O12—C49—C50 | 109.5 (2) |
C1—C9—C10 | 122.38 (19) | C19—C18—C17 | 127.5 (3) |
C11—C9—C10 | 109.89 (18) | C34—C35—C36 | 119.1 (2) |
C1—C9—C2 | 60.50 (14) | C65—C64—C63 | 118.4 (2) |
C11—C9—C2 | 118.86 (18) | C29—C28—C27 | 118.7 (2) |
C10—C9—C2 | 118.47 (18) | O14—C53—C54 | 109.39 (19) |
C37—C45—C46 | 121.82 (18) | N2—C36—C35 | 122.8 (2) |
C37—C45—C47 | 118.45 (18) | C62—C61—C60 | 123.3 (3) |
C46—C45—C47 | 110.67 (18) | O7—C23—O8 | 121.41 (19) |
C37—C45—C38 | 60.25 (13) | O7—C23—C4 | 126.2 (2) |
C46—C45—C38 | 118.85 (18) | O8—C23—C4 | 112.23 (18) |
C47—C45—C38 | 118.68 (18) | C28—C29—C30 | 119.0 (2) |
O1—C5—O2 | 121.7 (2) | C71—C70—C69 | 118.5 (2) |
O1—C5—C1 | 126.4 (2) | O6—C17—C18 | 108.6 (2) |
O2—C5—C1 | 111.71 (18) | C8—C7—C6 | 123.9 (3) |
C52—C39—C38 | 117.18 (18) | O2—C6—C7 | 106.7 (2) |
C52—C39—C40 | 118.60 (17) | C34—C33—C32 | 120.3 (2) |
C38—C39—C40 | 113.57 (16) | C15—C14—C13 | 126.7 (3) |
C52—C39—C56 | 118.63 (18) | C55—C54—C53 | 127.3 (2) |
C38—C39—C56 | 117.45 (17) | C26—C25—C24 | 122.5 (3) |
C40—C39—C56 | 58.05 (13) | C29—C30—C31 | 119.6 (2) |
C16—C3—C2 | 116.23 (18) | O10—C42—C43 | 109.9 (2) |
C16—C3—C4 | 119.06 (17) | C44—C43—C42 | 126.5 (3) |
| | | |
C37—Pd2—N3—C63 | 17.11 (19) | C40—C39—C52—O13 | −25.0 (3) |
N4—Pd2—N3—C63 | −173.26 (19) | C56—C39—C52—O13 | 42.1 (3) |
C37—Pd2—N3—C67 | −169.85 (15) | C38—C39—C52—O14 | 11.3 (3) |
N4—Pd2—N3—C67 | −0.22 (14) | C40—C39—C52—O14 | 153.69 (18) |
C40—Pd2—N4—C72 | 17.99 (18) | C56—C39—C52—O14 | −139.21 (18) |
N3—Pd2—N4—C72 | −171.92 (18) | C63—N3—C67—C66 | −0.6 (3) |
C40—Pd2—N4—C68 | −175.13 (14) | Pd2—N3—C67—C66 | −174.19 (16) |
N3—Pd2—N4—C68 | −5.04 (14) | C63—N3—C67—C68 | 178.69 (19) |
C1—Pd1—N1—C27 | −18.3 (2) | Pd2—N3—C67—C68 | 5.0 (2) |
N2—Pd1—N1—C27 | 173.18 (19) | N4—C68—C67—N3 | −9.6 (3) |
C1—Pd1—N1—C31 | 174.97 (15) | C69—C68—C67—N3 | 167.4 (2) |
N2—Pd1—N1—C31 | 6.49 (15) | N4—C68—C67—C66 | 169.6 (2) |
C4—Pd1—N2—C36 | −22.07 (19) | C69—C68—C67—C66 | −13.3 (3) |
N1—Pd1—N2—C36 | 169.29 (19) | C49—O12—C48—O11 | 5.4 (3) |
C4—Pd1—N2—C32 | 169.85 (15) | C49—O12—C48—C38 | −171.67 (18) |
N1—Pd1—N2—C32 | 1.21 (15) | C39—C38—C48—O11 | −164.0 (2) |
C40—Pd2—C37—C41 | −140.70 (16) | C37—C38—C48—O11 | −22.7 (3) |
N3—Pd2—C37—C41 | 48.80 (16) | C45—C38—C48—O11 | 44.2 (3) |
C40—Pd2—C37—C45 | 70.65 (17) | C39—C38—C48—O12 | 13.0 (3) |
N3—Pd2—C37—C45 | −99.85 (17) | C37—C38—C48—O12 | 154.35 (18) |
C40—Pd2—C37—C38 | −0.03 (14) | C45—C38—C48—O12 | −138.78 (19) |
N3—Pd2—C37—C38 | −170.53 (14) | C68—N4—C72—C71 | −0.5 (3) |
C37—Pd2—C40—C59 | −141.85 (16) | Pd2—N4—C72—C71 | 165.97 (17) |
N4—Pd2—C40—C59 | 47.71 (16) | C70—C71—C72—N4 | 0.5 (3) |
C37—Pd2—C40—C56 | 65.10 (18) | C36—N2—C32—C33 | 0.4 (3) |
N4—Pd2—C40—C56 | −105.34 (17) | Pd1—N2—C32—C33 | 169.39 (18) |
C37—Pd2—C40—C39 | −5.56 (14) | C36—N2—C32—C31 | −177.21 (19) |
N4—Pd2—C40—C39 | −176.00 (13) | Pd1—N2—C32—C31 | −8.2 (2) |
C12—C2—C1—C5 | 1.2 (3) | N1—C31—C32—N2 | 14.0 (3) |
C3—C2—C1—C5 | −143.19 (19) | C30—C31—C32—N2 | −165.5 (2) |
C9—C2—C1—C5 | 108.3 (2) | N1—C31—C32—C33 | −163.5 (2) |
C12—C2—C1—C9 | −107.2 (2) | C30—C31—C32—C33 | 17.0 (3) |
C3—C2—C1—C9 | 108.47 (19) | C42—O10—C41—O9 | 0.5 (3) |
C12—C2—C1—Pd1 | 133.41 (17) | C42—O10—C41—C37 | −174.2 (2) |
C3—C2—C1—Pd1 | −11.0 (2) | C45—C37—C41—O9 | 42.0 (3) |
C9—C2—C1—Pd1 | −119.43 (16) | C38—C37—C41—O9 | 114.1 (2) |
C4—Pd1—C1—C5 | 141.59 (16) | Pd2—C37—C41—O9 | −108.2 (2) |
N1—Pd1—C1—C5 | −48.97 (16) | C45—C37—C41—O10 | −143.42 (19) |
C4—Pd1—C1—C9 | −65.61 (18) | C38—C37—C41—O10 | −71.4 (2) |
N1—Pd1—C1—C9 | 103.83 (18) | Pd2—C37—C41—O10 | 66.3 (2) |
C4—Pd1—C1—C2 | 5.37 (14) | C67—N3—C63—C64 | 3.4 (3) |
N1—Pd1—C1—C2 | 174.81 (14) | Pd2—N3—C63—C64 | 176.29 (18) |
C27—N1—C31—C30 | −0.9 (3) | C23—O8—C24—C25 | −178.78 (19) |
Pd1—N1—C31—C30 | 166.90 (17) | C13—O4—C12—O3 | −3.0 (3) |
C27—N1—C31—C32 | 179.55 (19) | C13—O4—C12—C2 | 173.7 (2) |
Pd1—N1—C31—C32 | −12.6 (2) | C3—C2—C12—O3 | 168.8 (2) |
C72—N4—C68—C69 | 0.2 (3) | C1—C2—C12—O3 | 26.3 (3) |
Pd2—N4—C68—C69 | −167.84 (17) | C9—C2—C12—O3 | −39.8 (3) |
C72—N4—C68—C67 | 177.27 (18) | C3—C2—C12—O4 | −7.7 (3) |
Pd2—N4—C68—C67 | 9.2 (2) | C1—C2—C12—O4 | −150.19 (19) |
C5—C1—C9—C11 | 142.0 (2) | C9—C2—C12—O4 | 143.65 (19) |
C2—C1—C9—C11 | −108.6 (2) | C17—O6—C16—O5 | −3.0 (3) |
Pd1—C1—C9—C11 | −8.9 (3) | C17—O6—C16—C3 | 175.50 (19) |
C5—C1—C9—C10 | −2.5 (3) | C2—C3—C16—O5 | 158.7 (2) |
C2—C1—C9—C10 | 106.8 (2) | C4—C3—C16—O5 | 17.4 (3) |
Pd1—C1—C9—C10 | −153.45 (17) | C20—C3—C16—O5 | −49.8 (3) |
C5—C1—C9—C2 | −109.4 (2) | C2—C3—C16—O6 | −19.6 (3) |
Pd1—C1—C9—C2 | 99.71 (18) | C4—C3—C16—O6 | −160.96 (18) |
C12—C2—C9—C1 | 106.3 (2) | C20—C3—C16—O6 | 131.86 (19) |
C3—C2—C9—C1 | −101.9 (2) | C16—C3—C20—C4 | 108.5 (2) |
C12—C2—C9—C11 | −144.7 (2) | C2—C3—C20—C4 | −100.9 (2) |
C3—C2—C9—C11 | 7.2 (3) | C16—C3—C20—C21 | −2.9 (3) |
C1—C2—C9—C11 | 109.1 (2) | C2—C3—C20—C21 | 147.70 (19) |
C12—C2—C9—C10 | −6.9 (3) | C4—C3—C20—C21 | −111.4 (2) |
C3—C2—C9—C10 | 144.9 (2) | C16—C3—C20—C22 | −143.2 (2) |
C1—C2—C9—C10 | −113.1 (2) | C2—C3—C20—C22 | 7.4 (3) |
C41—C37—C45—C46 | 4.2 (3) | C4—C3—C20—C22 | 108.3 (2) |
C38—C37—C45—C46 | −107.4 (2) | C59—O16—C60—C61 | −176.45 (19) |
Pd2—C37—C45—C46 | 150.72 (17) | C21—C20—C4—C23 | −4.4 (3) |
C41—C37—C45—C47 | −139.7 (2) | C22—C20—C4—C23 | 140.1 (2) |
C38—C37—C45—C47 | 108.6 (2) | C3—C20—C4—C23 | −111.1 (2) |
Pd2—C37—C45—C47 | 6.8 (3) | C21—C20—C4—C3 | 106.6 (2) |
C41—C37—C45—C38 | 111.7 (2) | C22—C20—C4—C3 | −108.8 (2) |
Pd2—C37—C45—C38 | −101.85 (17) | C21—C20—C4—Pd1 | −152.43 (17) |
C6—O2—C5—O1 | 12.2 (3) | C22—C20—C4—Pd1 | −7.9 (3) |
C6—O2—C5—C1 | −172.79 (18) | C3—C20—C4—Pd1 | 100.93 (18) |
C9—C1—C5—O1 | −45.8 (3) | C16—C3—C4—C23 | 0.3 (3) |
C2—C1—C5—O1 | −117.0 (3) | C2—C3—C4—C23 | −142.02 (19) |
Pd1—C1—C5—O1 | 109.4 (2) | C20—C3—C4—C23 | 107.0 (2) |
C9—C1—C5—O2 | 139.44 (19) | C16—C3—C4—C20 | −106.7 (2) |
C2—C1—C5—O2 | 68.2 (2) | C2—C3—C4—C20 | 110.94 (19) |
Pd1—C1—C5—O2 | −65.4 (2) | C16—C3—C4—Pd1 | 134.82 (17) |
C59—C40—C39—C52 | 0.1 (3) | C2—C3—C4—Pd1 | −7.5 (2) |
C56—C40—C39—C52 | 107.6 (2) | C20—C3—C4—Pd1 | −118.46 (16) |
Pd2—C40—C39—C52 | −133.40 (16) | C1—Pd1—C4—C23 | 139.81 (16) |
C59—C40—C39—C38 | 143.76 (19) | N2—Pd1—C4—C23 | −51.13 (16) |
C56—C40—C39—C38 | −108.70 (19) | C1—Pd1—C4—C20 | −70.36 (18) |
Pd2—C40—C39—C38 | 10.3 (2) | N2—Pd1—C4—C20 | 98.70 (18) |
C59—C40—C39—C56 | −107.5 (2) | C1—Pd1—C4—C3 | 1.10 (15) |
Pd2—C40—C39—C56 | 118.96 (16) | N2—Pd1—C4—C3 | 170.16 (14) |
C12—C2—C3—C16 | 84.6 (2) | N4—C68—C69—C70 | 0.0 (3) |
C1—C2—C3—C16 | −131.65 (19) | C67—C68—C69—C70 | −176.8 (2) |
C9—C2—C3—C16 | −67.0 (2) | C12—O4—C13—C14 | −169.4 (2) |
C12—C2—C3—C4 | −132.0 (2) | C60—O16—C59—O15 | −18.2 (3) |
C1—C2—C3—C4 | 11.8 (2) | C60—O16—C59—C40 | 164.71 (17) |
C9—C2—C3—C4 | 76.5 (2) | C56—C40—C59—O15 | 45.0 (3) |
C12—C2—C3—C20 | −66.6 (3) | C39—C40—C59—O15 | 115.1 (2) |
C1—C2—C3—C20 | 77.2 (2) | Pd2—C40—C59—O15 | −110.5 (2) |
C9—C2—C3—C20 | 141.91 (19) | C56—C40—C59—O16 | −138.05 (19) |
C52—C39—C38—C48 | −83.1 (2) | C39—C40—C59—O16 | −68.0 (2) |
C40—C39—C38—C48 | 132.74 (19) | Pd2—C40—C59—O16 | 66.4 (2) |
C56—C39—C38—C48 | 67.8 (2) | C64—C65—C66—C67 | 2.6 (3) |
C52—C39—C38—C37 | 133.97 (18) | N3—C67—C66—C65 | −2.4 (3) |
C40—C39—C38—C37 | −10.2 (2) | C68—C67—C66—C65 | 178.4 (2) |
C56—C39—C38—C37 | −75.1 (2) | C31—N1—C27—C28 | −0.5 (3) |
C52—C39—C38—C45 | 68.6 (2) | Pd1—N1—C27—C28 | −166.68 (18) |
C40—C39—C38—C45 | −75.6 (2) | C48—O12—C49—C50 | 171.2 (2) |
C56—C39—C38—C45 | −140.48 (18) | C51—C50—C49—O12 | 6.1 (4) |
C41—C37—C38—C48 | −0.4 (3) | C33—C34—C35—C36 | 0.6 (4) |
C45—C37—C38—C48 | 107.4 (2) | C66—C65—C64—C63 | 0.0 (4) |
Pd2—C37—C38—C48 | −136.86 (16) | N3—C63—C64—C65 | −3.2 (4) |
C41—C37—C38—C39 | 142.22 (19) | N1—C27—C28—C29 | 1.4 (4) |
C45—C37—C38—C39 | −109.95 (19) | C52—O14—C53—C54 | −179.3 (2) |
Pd2—C37—C38—C39 | 5.8 (2) | C32—N2—C36—C35 | 0.2 (3) |
C41—C37—C38—C45 | −107.8 (2) | Pd1—N2—C36—C35 | −167.50 (18) |
Pd2—C37—C38—C45 | 115.72 (16) | C34—C35—C36—N2 | −0.7 (4) |
C37—C45—C38—C48 | −107.1 (2) | O16—C60—C61—C62 | −135.6 (3) |
C46—C45—C38—C48 | 5.2 (3) | C24—O8—C23—O7 | 15.7 (3) |
C47—C45—C38—C48 | 144.7 (2) | C24—O8—C23—C4 | −168.66 (18) |
C37—C45—C38—C39 | 101.5 (2) | C20—C4—C23—O7 | −43.6 (3) |
C46—C45—C38—C39 | −146.23 (19) | C3—C4—C23—O7 | −115.1 (3) |
C47—C45—C38—C39 | −6.7 (3) | Pd1—C4—C23—O7 | 108.9 (2) |
C46—C45—C38—C37 | 112.2 (2) | C20—C4—C23—O8 | 141.04 (19) |
C47—C45—C38—C37 | −108.2 (2) | C3—C4—C23—O8 | 69.5 (2) |
C59—C40—C56—C58 | −144.26 (19) | Pd1—C4—C23—O8 | −66.5 (2) |
C39—C40—C56—C58 | 107.4 (2) | C27—C28—C29—C30 | −1.0 (4) |
Pd2—C40—C56—C58 | 7.5 (3) | C72—C71—C70—C69 | −0.3 (4) |
C59—C40—C56—C57 | −0.3 (3) | C68—C69—C70—C71 | 0.0 (4) |
C39—C40—C56—C57 | −108.6 (2) | C16—O6—C17—C18 | 177.0 (2) |
Pd2—C40—C56—C57 | 151.45 (17) | C19—C18—C17—O6 | −0.8 (4) |
C59—C40—C56—C39 | 108.3 (2) | C5—O2—C6—C7 | 157.5 (2) |
Pd2—C40—C56—C39 | −99.93 (18) | C8—C7—C6—O2 | 126.1 (3) |
C52—C39—C56—C40 | −107.59 (19) | C35—C34—C33—C32 | 0.0 (4) |
C38—C39—C56—C40 | 101.95 (19) | N2—C32—C33—C34 | −0.4 (4) |
C52—C39—C56—C58 | 141.83 (19) | C31—C32—C33—C34 | 177.0 (2) |
C38—C39—C56—C58 | −8.6 (3) | O4—C13—C14—C15 | −5.3 (4) |
C40—C39—C56—C58 | −110.6 (2) | O14—C53—C54—C55 | 3.6 (4) |
C52—C39—C56—C57 | 4.2 (3) | O8—C24—C25—C26 | 116.9 (3) |
C38—C39—C56—C57 | −146.24 (19) | C28—C29—C30—C31 | −0.3 (4) |
C40—C39—C56—C57 | 111.8 (2) | N1—C31—C30—C29 | 1.3 (3) |
C53—O14—C52—O13 | 2.0 (3) | C32—C31—C30—C29 | −179.2 (2) |
C53—O14—C52—C39 | −176.84 (18) | C41—O10—C42—C43 | −162.3 (2) |
C38—C39—C52—O13 | −167.4 (2) | O10—C42—C43—C44 | 19.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O3 | 0.96 | 2.22 | 2.916 (3) | 128 |
C11—H11C···O8 | 0.96 | 2.30 | 3.255 (3) | 173 |
C21—H21B···O5 | 0.96 | 2.26 | 3.016 (3) | 135 |
C22—H22C···O2 | 0.96 | 2.40 | 3.358 (3) | 176 |
C27—H27···O1 | 0.93 | 2.33 | 3.093 (3) | 139 |
C36—H36···O7 | 0.93 | 2.41 | 3.105 (3) | 132 |
C46—H46C···O11 | 0.96 | 2.28 | 2.982 (3) | 129 |
C47—H47B···O16 | 0.96 | 2.35 | 3.297 (3) | 171 |
C57—H57C···O13 | 0.96 | 2.25 | 2.979 (3) | 132 |
C58—H58B···O10 | 0.96 | 2.34 | 3.286 (3) | 168 |
C63—H63···O9 | 0.93 | 2.28 | 2.974 (3) | 131 |
C72—H72···O15 | 0.93 | 2.39 | 3.182 (3) | 143 |
C8—H8A···O13i | 0.93 | 2.57 | 3.346 (3) | 141 |
C19—H19B···O9ii | 0.93 | 2.53 | 3.397 (3) | 156 |
C24—H24B···O7iii | 0.97 | 2.58 | 3.483 (3) | 156 |
C60—H60A···O15iv | 0.97 | 2.46 | 3.392 (3) | 161 |
Symmetry codes: (i) −x−1, −y, −z+1; (ii) x+1, y, z; (iii) −x, −y−1, −z; (iv) −x−1, −y+1, −z+1. |
(I205K) tetraallyl (2,2'-bipyridyl)-rac-3,3,7,7-tetramethyl-
trans-5-palladatricyclo [4.1.0.0
2,4]heptane-1,2,4,6-tetracarboxylate
top
Crystal data top
[Pd(C10H8N2)(C26H32O8)] | Z = 2 |
Mr = 735.10 | F(000) = 760 |
Triclinic, P1 | Dx = 1.422 Mg m−3 |
a = 8.9583 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.3245 (18) Å | Cell parameters from 155 reflections |
c = 17.906 (3) Å | θ = 3–23° |
α = 83.438 (16)° | µ = 0.59 mm−1 |
β = 88.482 (14)° | T = 205 K |
γ = 72.118 (16)° | Plate, yellow |
V = 1717.4 (4) Å3 | 0.44 × 0.17 × 0.04 mm |
Data collection top
SIEMENS SMART diffractometer | 10543 independent reflections |
Radiation source: normal-focus sealed tube | 8751 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
ω scans | θmax = 31.2°, θmin = 1.9° |
Absorption correction: numerical (SHELXTL; sheldrick, 1996) ? | h = −12→13 |
Tmin = 0.791, Tmax = 0.977 | k = −15→16 |
31971 measured reflections | l = −24→26 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-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 reflections | Δρmax = 0.56 e Å−3 |
451 parameters | Δρmin = −0.55 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0020 (6) |
Crystal data top
[Pd(C10H8N2)(C26H32O8)] | γ = 72.118 (16)° |
Mr = 735.10 | V = 1717.4 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9583 (8) Å | Mo Kα radiation |
b = 11.3245 (18) Å | µ = 0.59 mm−1 |
c = 17.906 (3) Å | T = 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 = 0.977 | Rint = 0.070 |
31971 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.31 | Δρmax = 0.56 e Å−3 |
10543 reflections | Δρmin = −0.55 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Pd | −0.180174 (18) | 0.431505 (14) | 0.343610 (8) | 0.02450 (6) | |
C14 | −0.5109 (4) | 0.2234 (3) | 0.04479 (17) | 0.0593 (8) | |
H14 | −0.5961 | 0.2357 | 0.0131 | 0.071* | |
N2 | −0.2411 (2) | 0.41538 (17) | 0.45833 (9) | 0.0296 (4) | |
C3 | −0.1596 (2) | 0.24489 (17) | 0.23259 (10) | 0.0225 (4) | |
C1 | −0.1684 (2) | 0.47267 (18) | 0.22952 (11) | 0.0266 (4) | |
O8 | 0.08206 (18) | 0.13876 (14) | 0.36380 (8) | 0.0340 (3) | |
O7 | −0.1232 (2) | 0.09300 (15) | 0.41946 (9) | 0.0398 (4) | |
C2 | −0.1733 (2) | 0.36538 (18) | 0.18448 (10) | 0.0240 (4) | |
O5 | −0.00261 (19) | 0.02805 (13) | 0.24253 (8) | 0.0354 (3) | |
C4 | −0.1721 (2) | 0.25793 (18) | 0.31740 (10) | 0.0240 (4) | |
O4 | −0.33138 (18) | 0.30129 (15) | 0.10504 (9) | 0.0367 (4) | |
O6 | −0.00686 (18) | 0.15138 (14) | 0.13504 (8) | 0.0343 (3) | |
N1 | −0.1505 (2) | 0.59423 (17) | 0.37945 (10) | 0.0322 (4) | |
C31 | −0.1715 (3) | 0.6044 (2) | 0.45389 (12) | 0.0319 (4) | |
C16 | −0.0508 (2) | 0.12942 (19) | 0.20628 (11) | 0.0266 (4) | |
C23 | −0.0733 (3) | 0.15511 (19) | 0.37106 (11) | 0.0285 (4) | |
C9 | −0.0308 (2) | 0.41691 (19) | 0.18144 (11) | 0.0274 (4) | |
C10 | 0.0035 (3) | 0.4858 (2) | 0.10819 (13) | 0.0374 (5) | |
H10A | 0.0713 | 0.5335 | 0.1181 | 0.056* | |
H10B | −0.0929 | 0.5409 | 0.0862 | 0.056* | |
H10C | 0.0539 | 0.4265 | 0.0740 | 0.056* | |
C32 | −0.2335 (3) | 0.5098 (2) | 0.49604 (12) | 0.0328 (5) | |
O1 | −0.2294 (2) | 0.69030 (15) | 0.18181 (10) | 0.0463 (4) | |
C5 | −0.2725 (3) | 0.6018 (2) | 0.20539 (12) | 0.0343 (5) | |
O2 | −0.4255 (2) | 0.61324 (16) | 0.21831 (10) | 0.0486 (5) | |
O3 | −0.3243 (2) | 0.49795 (16) | 0.08057 (9) | 0.0448 (4) | |
C20 | −0.3042 (2) | 0.2322 (2) | 0.27922 (11) | 0.0274 (4) | |
C22 | −0.4595 (3) | 0.3355 (2) | 0.26608 (14) | 0.0391 (5) | |
H22A | −0.5241 | 0.3347 | 0.3097 | 0.059* | |
H22B | −0.5120 | 0.3221 | 0.2232 | 0.059* | |
H22C | −0.4403 | 0.4147 | 0.2570 | 0.059* | |
C12 | −0.2811 (3) | 0.3971 (2) | 0.11803 (11) | 0.0309 (4) | |
C27 | −0.0933 (3) | 0.6772 (2) | 0.33839 (14) | 0.0416 (5) | |
H27 | −0.0762 | 0.6699 | 0.2874 | 0.050* | |
C28 | −0.0585 (3) | 0.7731 (2) | 0.36852 (16) | 0.0460 (6) | |
H28 | −0.0208 | 0.8297 | 0.3381 | 0.055* | |
C21 | −0.3325 (3) | 0.1066 (2) | 0.29257 (14) | 0.0412 (5) | |
H21A | −0.3859 | 0.1007 | 0.3394 | 0.062* | |
H21B | −0.2338 | 0.0415 | 0.2944 | 0.062* | |
H21C | −0.3957 | 0.0978 | 0.2524 | 0.062* | |
C17 | 0.1020 (3) | 0.0462 (2) | 0.10419 (14) | 0.0470 (6) | |
H17A | 0.0575 | −0.0221 | 0.1064 | 0.056* | |
H17B | 0.1987 | 0.0180 | 0.1333 | 0.056* | |
C11 | 0.1221 (3) | 0.3365 (2) | 0.21973 (13) | 0.0358 (5) | |
H11A | 0.1806 | 0.3891 | 0.2334 | 0.054* | |
H11B | 0.1826 | 0.2807 | 0.1859 | 0.054* | |
H11C | 0.0994 | 0.2891 | 0.2641 | 0.054* | |
C33 | −0.2856 (3) | 0.5180 (2) | 0.56984 (13) | 0.0465 (6) | |
H33 | −0.2745 | 0.5810 | 0.5962 | 0.056* | |
C13 | −0.4523 (4) | 0.3304 (3) | 0.04709 (16) | 0.0556 (8) | |
H13A | −0.4092 | 0.3498 | −0.0014 | 0.067* | |
H13B | −0.5379 | 0.4030 | 0.0578 | 0.067* | |
C36 | −0.3075 (3) | 0.3320 (2) | 0.49193 (13) | 0.0377 (5) | |
H36 | −0.3140 | 0.2674 | 0.4658 | 0.045* | |
C35 | −0.3667 (3) | 0.3387 (3) | 0.56397 (14) | 0.0491 (7) | |
H35 | −0.4146 | 0.2809 | 0.5852 | 0.059* | |
C30 | −0.1357 (3) | 0.6972 (2) | 0.48700 (14) | 0.0419 (6) | |
H30 | −0.1490 | 0.7016 | 0.5384 | 0.050* | |
C24 | 0.1832 (3) | 0.0201 (2) | 0.39897 (14) | 0.0453 (6) | |
H24A | 0.1670 | −0.0471 | 0.3753 | 0.054* | 0.596 (9) |
H24B | 0.1572 | 0.0092 | 0.4512 | 0.054* | 0.596 (9) |
H24C | 0.1266 | −0.0405 | 0.4054 | 0.054* | 0.404 (9) |
H24D | 0.2173 | 0.0295 | 0.4477 | 0.054* | 0.404 (9) |
C19 | 0.0732 (4) | 0.1883 (3) | −0.01334 (16) | 0.0655 (9) | |
H19A | −0.0023 | 0.2516 | 0.0079 | 0.079* | |
H19B | 0.1035 | 0.2015 | −0.0629 | 0.079* | |
C18 | 0.1348 (4) | 0.0841 (3) | 0.02535 (15) | 0.0564 (7) | |
H18 | 0.2094 | 0.0245 | 0.0012 | 0.068* | |
C29 | −0.0802 (3) | 0.7834 (2) | 0.44336 (16) | 0.0481 (6) | |
H29 | −0.0581 | 0.8473 | 0.4648 | 0.058* | |
C34 | −0.3538 (4) | 0.4314 (3) | 0.60340 (14) | 0.0543 (7) | |
H34 | −0.3905 | 0.4363 | 0.6524 | 0.065* | |
C15 | −0.4571 (4) | 0.1131 (3) | 0.08207 (19) | 0.0649 (8) | |
H15A | −0.3719 | 0.0955 | 0.1146 | 0.078* | |
H15B | −0.5038 | 0.0518 | 0.0762 | 0.078* | |
C8 | −0.8277 (6) | 0.7376 (5) | 0.1961 (3) | 0.0602 (16) | 0.613 (7) |
H8A | −0.8419 | 0.8017 | 0.2262 | 0.072* | 0.613 (7) |
H8B | −0.9120 | 0.7105 | 0.1853 | 0.072* | 0.613 (7) |
C25 | 0.3401 (6) | 0.0164 (6) | 0.3921 (4) | 0.0579 (18) | 0.596 (9) |
H25 | 0.3726 | 0.0462 | 0.3459 | 0.070* | 0.596 (9) |
C26 | 0.4449 (8) | −0.0263 (8) | 0.4465 (5) | 0.108 (4) | 0.596 (9) |
H26A | 0.4162 | −0.0566 | 0.4934 | 0.130* | 0.596 (9) |
H26B | 0.5477 | −0.0261 | 0.4382 | 0.130* | 0.596 (9) |
C25' | 0.3273 (10) | −0.0251 (10) | 0.3465 (7) | 0.069 (3) | 0.404 (9) |
H25B | 0.3026 | −0.0061 | 0.2956 | 0.083* | 0.404 (9) |
C26' | 0.4677 (12) | −0.0812 (8) | 0.3597 (11) | 0.114 (7) | 0.404 (9) |
H26C | 0.5036 | −0.1042 | 0.4091 | 0.137* | 0.404 (9) |
H26D | 0.5372 | −0.1004 | 0.3202 | 0.137* | 0.404 (9) |
C6 | −0.5469 (5) | 0.7185 (4) | 0.1810 (3) | 0.0410 (11)* | 0.613 (7) |
H6A | −0.5083 | 0.7459 | 0.1331 | 0.049* | 0.613 (7) |
H6B | −0.5721 | 0.7873 | 0.2116 | 0.049* | 0.613 (7) |
C7 | −0.6881 (6) | 0.6851 (5) | 0.1685 (3) | 0.0501 (13)* | 0.613 (7) |
H7A | −0.6790 | 0.6213 | 0.1386 | 0.060* | 0.613 (7) |
C7' | −0.6837 (10) | 0.7529 (8) | 0.2061 (5) | 0.061 (3)* | 0.387 (7) |
H7'A | −0.7571 | 0.8246 | 0.2201 | 0.074* | 0.387 (7) |
C6' | −0.5195 (9) | 0.7501 (8) | 0.2082 (5) | 0.055 (2)* | 0.387 (7) |
H6'A | −0.5007 | 0.7917 | 0.2498 | 0.066* | 0.387 (7) |
H6'B | −0.4916 | 0.7910 | 0.1618 | 0.066* | 0.387 (7) |
C8' | −0.7357 (16) | 0.6726 (12) | 0.1881 (6) | 0.078 (3)* | 0.387 (7) |
H8'A | −0.6678 | 0.5988 | 0.1736 | 0.093* | 0.387 (7) |
H8'B | −0.8432 | 0.6850 | 0.1890 | 0.093* | 0.387 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd | 0.03211 (9) | 0.02283 (8) | 0.01928 (8) | −0.00983 (6) | 0.00041 (5) | −0.00133 (5) |
C14 | 0.0556 (17) | 0.079 (2) | 0.0516 (17) | −0.0286 (16) | −0.0151 (14) | −0.0154 (16) |
N2 | 0.0331 (9) | 0.0298 (9) | 0.0242 (8) | −0.0075 (7) | 0.0010 (7) | −0.0020 (7) |
C3 | 0.0247 (9) | 0.0225 (9) | 0.0203 (8) | −0.0079 (7) | −0.0011 (7) | −0.0002 (7) |
C1 | 0.0343 (10) | 0.0239 (9) | 0.0208 (9) | −0.0090 (8) | −0.0014 (8) | 0.0013 (7) |
O8 | 0.0373 (8) | 0.0299 (8) | 0.0319 (8) | −0.0085 (6) | −0.0108 (6) | 0.0069 (6) |
O7 | 0.0531 (10) | 0.0351 (8) | 0.0280 (8) | −0.0133 (7) | 0.0024 (7) | 0.0087 (7) |
C2 | 0.0284 (9) | 0.0243 (9) | 0.0178 (8) | −0.0071 (7) | −0.0020 (7) | 0.0019 (7) |
O5 | 0.0481 (9) | 0.0224 (7) | 0.0312 (8) | −0.0055 (6) | −0.0019 (7) | 0.0008 (6) |
C4 | 0.0296 (9) | 0.0231 (9) | 0.0196 (8) | −0.0095 (7) | 0.0006 (7) | 0.0002 (7) |
O4 | 0.0403 (8) | 0.0363 (8) | 0.0322 (8) | −0.0096 (7) | −0.0153 (7) | −0.0012 (7) |
O6 | 0.0425 (8) | 0.0292 (8) | 0.0253 (7) | −0.0025 (6) | 0.0062 (6) | −0.0036 (6) |
N1 | 0.0408 (10) | 0.0276 (9) | 0.0287 (9) | −0.0109 (8) | −0.0035 (8) | −0.0033 (7) |
C31 | 0.0329 (10) | 0.0289 (10) | 0.0298 (10) | −0.0020 (8) | −0.0061 (8) | −0.0052 (8) |
C16 | 0.0288 (10) | 0.0273 (10) | 0.0235 (9) | −0.0086 (8) | −0.0037 (8) | −0.0015 (8) |
C23 | 0.0416 (11) | 0.0242 (9) | 0.0200 (9) | −0.0112 (8) | −0.0038 (8) | −0.0001 (7) |
C9 | 0.0317 (10) | 0.0261 (10) | 0.0246 (9) | −0.0109 (8) | 0.0007 (8) | 0.0017 (8) |
C10 | 0.0471 (13) | 0.0375 (12) | 0.0298 (11) | −0.0195 (10) | 0.0073 (10) | 0.0040 (9) |
C32 | 0.0350 (11) | 0.0314 (11) | 0.0263 (10) | −0.0015 (9) | −0.0022 (8) | −0.0038 (8) |
O1 | 0.0684 (12) | 0.0269 (8) | 0.0412 (9) | −0.0140 (8) | 0.0025 (8) | 0.0042 (7) |
C5 | 0.0490 (13) | 0.0277 (11) | 0.0226 (10) | −0.0077 (9) | −0.0012 (9) | 0.0016 (8) |
O2 | 0.0427 (9) | 0.0355 (9) | 0.0516 (11) | 0.0048 (7) | 0.0054 (8) | 0.0131 (8) |
O3 | 0.0574 (11) | 0.0384 (9) | 0.0337 (9) | −0.0122 (8) | −0.0209 (8) | 0.0137 (7) |
C20 | 0.0291 (10) | 0.0315 (10) | 0.0235 (9) | −0.0124 (8) | −0.0002 (8) | −0.0011 (8) |
C22 | 0.0274 (10) | 0.0479 (14) | 0.0405 (13) | −0.0100 (10) | 0.0043 (9) | −0.0038 (10) |
C12 | 0.0329 (10) | 0.0338 (11) | 0.0228 (9) | −0.0057 (8) | −0.0033 (8) | −0.0014 (8) |
C27 | 0.0567 (15) | 0.0348 (12) | 0.0380 (12) | −0.0215 (11) | −0.0013 (11) | −0.0018 (10) |
C28 | 0.0551 (15) | 0.0316 (12) | 0.0537 (16) | −0.0177 (11) | −0.0129 (12) | 0.0010 (11) |
C21 | 0.0479 (14) | 0.0437 (13) | 0.0410 (13) | −0.0278 (11) | 0.0017 (11) | −0.0034 (11) |
C17 | 0.0537 (15) | 0.0378 (13) | 0.0404 (13) | 0.0015 (11) | 0.0095 (11) | −0.0125 (10) |
C11 | 0.0286 (10) | 0.0400 (12) | 0.0390 (12) | −0.0129 (9) | −0.0013 (9) | 0.0016 (10) |
C33 | 0.0609 (16) | 0.0425 (13) | 0.0295 (11) | −0.0041 (12) | 0.0060 (11) | −0.0115 (10) |
C13 | 0.0619 (17) | 0.0596 (18) | 0.0462 (15) | −0.0191 (14) | −0.0309 (13) | −0.0005 (13) |
C36 | 0.0425 (12) | 0.0349 (12) | 0.0328 (11) | −0.0097 (10) | 0.0067 (9) | 0.0013 (9) |
C35 | 0.0518 (15) | 0.0457 (15) | 0.0404 (14) | −0.0076 (12) | 0.0134 (11) | 0.0094 (11) |
C30 | 0.0514 (14) | 0.0348 (12) | 0.0387 (12) | −0.0080 (10) | −0.0080 (11) | −0.0137 (10) |
C24 | 0.0512 (14) | 0.0365 (13) | 0.0370 (13) | −0.0016 (11) | −0.0091 (11) | 0.0111 (10) |
C19 | 0.099 (3) | 0.066 (2) | 0.0381 (15) | −0.0349 (19) | 0.0187 (16) | −0.0067 (14) |
C18 | 0.0686 (19) | 0.0582 (18) | 0.0410 (14) | −0.0144 (15) | 0.0161 (13) | −0.0170 (13) |
C29 | 0.0560 (15) | 0.0296 (12) | 0.0608 (17) | −0.0126 (11) | −0.0150 (13) | −0.0113 (11) |
C34 | 0.0673 (18) | 0.0511 (16) | 0.0307 (12) | 0.0000 (13) | 0.0152 (12) | −0.0025 (11) |
C15 | 0.070 (2) | 0.074 (2) | 0.065 (2) | −0.0372 (18) | 0.0035 (16) | −0.0236 (18) |
C8 | 0.053 (3) | 0.039 (2) | 0.075 (4) | 0.003 (2) | 0.003 (2) | 0.004 (2) |
C25 | 0.037 (2) | 0.064 (4) | 0.065 (4) | −0.018 (2) | −0.008 (3) | 0.030 (3) |
C26 | 0.054 (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—C1 | 2.0503 (19) | C31—C30 | 1.386 (3) |
Pd—C4 | 2.052 (2) | C31—C32 | 1.477 (3) |
Pd—N1 | 2.1114 (18) | C9—C10 | 1.522 (3) |
Pd—N2 | 2.1136 (17) | C9—C11 | 1.522 (3) |
C14—C15 | 1.302 (5) | C32—C33 | 1.393 (3) |
C14—C13 | 1.466 (4) | O1—C5 | 1.210 (3) |
N2—C36 | 1.343 (3) | C5—O2 | 1.353 (3) |
N2—C32 | 1.348 (3) | O2—C6 | 1.453 (4) |
C3—C16 | 1.489 (3) | O2—C6' | 1.512 (8) |
C3—C2 | 1.501 (3) | O3—C12 | 1.213 (3) |
C3—C4 | 1.540 (3) | C20—C21 | 1.511 (3) |
C3—C20 | 1.557 (3) | C20—C22 | 1.521 (3) |
C1—C5 | 1.495 (3) | C27—C28 | 1.385 (3) |
C1—C9 | 1.499 (3) | C28—C29 | 1.362 (4) |
C1—C2 | 1.545 (3) | C17—C18 | 1.477 (4) |
O8—C23 | 1.351 (3) | C33—C34 | 1.381 (4) |
O8—C24 | 1.453 (3) | C36—C35 | 1.383 (3) |
O7—C23 | 1.216 (2) | C35—C34 | 1.365 (4) |
C2—C12 | 1.492 (3) | C30—C29 | 1.383 (4) |
C2—C9 | 1.555 (3) | C24—C25 | 1.396 (6) |
O5—C16 | 1.211 (2) | C24—C25' | 1.565 (10) |
C4—C23 | 1.490 (3) | C19—C18 | 1.269 (4) |
C4—C20 | 1.501 (3) | C8—C7 | 1.319 (8) |
O4—C12 | 1.341 (3) | C25—C26 | 1.314 (8) |
O4—C13 | 1.456 (3) | C25'—C26' | 1.237 (12) |
O6—C16 | 1.343 (2) | C6—C7 | 1.457 (7) |
O6—C17 | 1.443 (3) | C7'—C8' | 1.218 (14) |
N1—C27 | 1.343 (3) | C7'—C6' | 1.463 (12) |
N1—C31 | 1.354 (3) | | |
| | | |
C1—Pd—C4 | 84.20 (8) | O7—C23—O8 | 121.32 (19) |
C1—Pd—N1 | 99.77 (8) | O7—C23—C4 | 125.1 (2) |
C4—Pd—N1 | 170.14 (7) | O8—C23—C4 | 113.55 (17) |
C1—Pd—N2 | 167.86 (7) | C1—C9—C10 | 122.30 (18) |
C4—Pd—N2 | 100.09 (7) | C1—C9—C11 | 118.63 (17) |
N1—Pd—N2 | 77.87 (7) | C10—C9—C11 | 109.95 (18) |
C15—C14—C13 | 127.4 (3) | C1—C9—C2 | 60.74 (13) |
C36—N2—C32 | 118.65 (19) | C10—C9—C2 | 118.88 (17) |
C36—N2—Pd | 125.52 (16) | C11—C9—C2 | 118.82 (17) |
C32—N2—Pd | 114.98 (15) | N2—C32—C33 | 121.1 (2) |
C16—C3—C2 | 116.75 (16) | N2—C32—C31 | 116.13 (19) |
C16—C3—C4 | 119.32 (16) | C33—C32—C31 | 122.7 (2) |
C2—C3—C4 | 113.59 (16) | O1—C5—O2 | 121.9 (2) |
C16—C3—C20 | 117.49 (17) | O1—C5—C1 | 125.9 (2) |
C2—C3—C20 | 118.71 (16) | O2—C5—C1 | 112.01 (19) |
C4—C3—C20 | 57.96 (12) | C5—O2—C6 | 120.1 (2) |
C5—C1—C9 | 118.58 (17) | C5—O2—C6' | 109.0 (4) |
C5—C1—C2 | 118.82 (17) | C4—C20—C21 | 121.65 (18) |
C9—C1—C2 | 61.42 (13) | C4—C20—C22 | 119.22 (18) |
C5—C1—Pd | 110.33 (14) | C21—C20—C22 | 110.06 (19) |
C9—C1—Pd | 125.45 (14) | C4—C20—C3 | 60.45 (13) |
C2—C1—Pd | 113.66 (13) | C21—C20—C3 | 119.41 (19) |
C23—O8—C24 | 114.98 (18) | C22—C20—C3 | 118.38 (17) |
C12—C2—C3 | 117.10 (17) | O3—C12—O4 | 122.52 (19) |
C12—C2—C1 | 117.78 (16) | O3—C12—C2 | 125.4 (2) |
C3—C2—C1 | 113.73 (15) | O4—C12—C2 | 112.06 (17) |
C12—C2—C9 | 118.57 (17) | N1—C27—C28 | 123.0 (2) |
C3—C2—C9 | 118.25 (16) | C29—C28—C27 | 119.1 (2) |
C1—C2—C9 | 57.84 (13) | O6—C17—C18 | 109.2 (2) |
C23—C4—C20 | 116.81 (17) | C34—C33—C32 | 119.3 (2) |
C23—C4—C3 | 119.08 (17) | O4—C13—C14 | 109.7 (2) |
C20—C4—C3 | 61.59 (13) | N2—C36—C35 | 122.5 (2) |
C23—C4—Pd | 112.68 (13) | C34—C35—C36 | 119.0 (3) |
C20—C4—Pd | 123.47 (14) | C29—C30—C31 | 119.8 (2) |
C3—C4—Pd | 113.98 (12) | C25—C24—O8 | 110.1 (3) |
C12—O4—C13 | 115.01 (18) | O8—C24—C25' | 107.9 (3) |
C16—O6—C17 | 115.75 (17) | C19—C18—C17 | 127.7 (3) |
C27—N1—C31 | 117.8 (2) | C28—C29—C30 | 118.9 (2) |
C27—N1—Pd | 126.33 (16) | C35—C34—C33 | 119.3 (2) |
C31—N1—Pd | 115.16 (15) | C26—C25—C24 | 124.3 (5) |
N1—C31—C30 | 121.4 (2) | C26'—C25'—C24 | 132.5 (11) |
N1—C31—C32 | 115.24 (19) | O2—C6—C7 | 111.2 (4) |
C30—C31—C32 | 123.4 (2) | C8—C7—C6 | 125.5 (5) |
O5—C16—O6 | 122.39 (19) | C8'—C7'—C6' | 127.7 (11) |
O5—C16—C3 | 126.64 (19) | C7'—C6'—O2 | 105.4 (7) |
O6—C16—C3 | 110.96 (16) | | |
| | | |
C4—Pd—N2—C36 | −20.15 (19) | C12—C2—C9—C10 | −6.4 (3) |
N1—Pd—N2—C36 | 169.69 (19) | C3—C2—C9—C10 | 145.38 (19) |
C4—Pd—N2—C32 | 170.63 (15) | C1—C2—C9—C10 | −113.0 (2) |
N1—Pd—N2—C32 | 0.47 (15) | C12—C2—C9—C11 | −144.9 (2) |
C4—Pd—C1—C5 | 140.93 (16) | C3—C2—C9—C11 | 6.9 (3) |
N1—Pd—C1—C5 | −48.19 (16) | C1—C2—C9—C11 | 108.6 (2) |
C4—Pd—C1—C9 | −66.20 (18) | C36—N2—C32—C33 | 3.4 (3) |
N1—Pd—C1—C9 | 104.69 (18) | Pd—N2—C32—C33 | 173.38 (18) |
C4—Pd—C1—C2 | 4.58 (14) | C36—N2—C32—C31 | −174.96 (19) |
N1—Pd—C1—C2 | 175.47 (14) | Pd—N2—C32—C31 | −5.0 (2) |
C16—C3—C2—C12 | 82.2 (2) | N1—C31—C32—N2 | 8.9 (3) |
C4—C3—C2—C12 | −132.87 (18) | C30—C31—C32—N2 | −170.8 (2) |
C20—C3—C2—C12 | −67.8 (2) | N1—C31—C32—C33 | −169.4 (2) |
C16—C3—C2—C1 | −134.97 (18) | C30—C31—C32—C33 | 10.9 (3) |
C4—C3—C2—C1 | 10.0 (2) | C9—C1—C5—O1 | −44.0 (3) |
C20—C3—C2—C1 | 75.1 (2) | C2—C1—C5—O1 | −115.2 (3) |
C16—C3—C2—C9 | −70.0 (2) | Pd—C1—C5—O1 | 111.0 (2) |
C4—C3—C2—C9 | 74.9 (2) | C9—C1—C5—O2 | 140.9 (2) |
C20—C3—C2—C9 | 140.01 (18) | C2—C1—C5—O2 | 69.7 (2) |
C5—C1—C2—C12 | 0.9 (3) | Pd—C1—C5—O2 | −64.1 (2) |
C9—C1—C2—C12 | −107.90 (19) | O1—C5—O2—C6 | 21.6 (4) |
Pd—C1—C2—C12 | 133.26 (16) | C1—C5—O2—C6 | −163.1 (3) |
C5—C1—C2—C3 | −141.68 (19) | O1—C5—O2—C6' | −7.1 (5) |
C9—C1—C2—C3 | 109.53 (18) | C1—C5—O2—C6' | 168.2 (4) |
Pd—C1—C2—C3 | −9.3 (2) | C23—C4—C20—C21 | −2.0 (3) |
C5—C1—C2—C9 | 108.8 (2) | C3—C4—C20—C21 | 108.3 (2) |
Pd—C1—C2—C9 | −118.85 (15) | Pd—C4—C20—C21 | −150.40 (17) |
C16—C3—C4—C23 | 0.8 (3) | C23—C4—C20—C22 | 141.78 (19) |
C2—C3—C4—C23 | −143.19 (18) | C3—C4—C20—C22 | −108.0 (2) |
C20—C3—C4—C23 | 106.6 (2) | Pd—C4—C20—C22 | −6.7 (3) |
C16—C3—C4—C20 | −105.9 (2) | C23—C4—C20—C3 | −110.23 (19) |
C2—C3—C4—C20 | 110.19 (18) | Pd—C4—C20—C3 | 101.32 (16) |
C16—C3—C4—Pd | 137.68 (15) | C16—C3—C20—C4 | 109.00 (18) |
C2—C3—C4—Pd | −6.3 (2) | C2—C3—C20—C4 | −101.28 (19) |
C20—C3—C4—Pd | −116.46 (15) | C16—C3—C20—C21 | −2.9 (3) |
C1—Pd—C4—C23 | 140.53 (15) | C2—C3—C20—C21 | 146.83 (19) |
N2—Pd—C4—C23 | −50.93 (15) | C4—C3—C20—C21 | −111.9 (2) |
C1—Pd—C4—C20 | −69.87 (16) | C16—C3—C20—C22 | −141.65 (19) |
N2—Pd—C4—C20 | 98.66 (16) | C2—C3—C20—C22 | 8.1 (3) |
C1—Pd—C4—C3 | 0.85 (14) | C4—C3—C20—C22 | 109.4 (2) |
N2—Pd—C4—C3 | 169.38 (13) | C13—O4—C12—O3 | −5.3 (3) |
C1—Pd—N1—C27 | −17.4 (2) | C13—O4—C12—C2 | 172.5 (2) |
N2—Pd—N1—C27 | 174.7 (2) | C3—C2—C12—O3 | 167.9 (2) |
C1—Pd—N1—C31 | 172.32 (15) | C1—C2—C12—O3 | 26.6 (3) |
N2—Pd—N1—C31 | 4.45 (15) | C9—C2—C12—O3 | −40.0 (3) |
C27—N1—C31—C30 | 0.2 (3) | C3—C2—C12—O4 | −9.8 (3) |
Pd—N1—C31—C30 | 171.33 (17) | C1—C2—C12—O4 | −151.16 (18) |
C27—N1—C31—C32 | −179.5 (2) | C9—C2—C12—O4 | 142.30 (19) |
Pd—N1—C31—C32 | −8.3 (2) | C31—N1—C27—C28 | −1.4 (4) |
C17—O6—C16—O5 | 0.0 (3) | Pd—N1—C27—C28 | −171.48 (19) |
C17—O6—C16—C3 | 178.59 (19) | N1—C27—C28—C29 | 1.2 (4) |
C2—C3—C16—O5 | 166.1 (2) | C16—O6—C17—C18 | 178.3 (2) |
C4—C3—C16—O5 | 23.2 (3) | N2—C32—C33—C34 | −3.5 (4) |
C20—C3—C16—O5 | −43.6 (3) | C31—C32—C33—C34 | 174.7 (2) |
C2—C3—C16—O6 | −12.5 (2) | C12—O4—C13—C14 | −173.0 (2) |
C4—C3—C16—O6 | −155.35 (17) | C15—C14—C13—O4 | −6.4 (5) |
C20—C3—C16—O6 | 137.82 (17) | C32—N2—C36—C35 | −0.8 (3) |
C24—O8—C23—O7 | 19.3 (3) | Pd—N2—C36—C35 | −169.62 (18) |
C24—O8—C23—C4 | −163.38 (18) | N2—C36—C35—C34 | −1.7 (4) |
C20—C4—C23—O7 | −46.5 (3) | N1—C31—C30—C29 | 1.3 (3) |
C3—C4—C23—O7 | −117.3 (2) | C32—C31—C30—C29 | −179.1 (2) |
Pd—C4—C23—O7 | 105.2 (2) | C23—O8—C24—C25 | −176.3 (4) |
C20—C4—C23—O8 | 136.22 (18) | C23—O8—C24—C25' | 141.9 (6) |
C3—C4—C23—O8 | 65.4 (2) | O6—C17—C18—C19 | −4.2 (5) |
Pd—C4—C23—O8 | −72.01 (19) | C27—C28—C29—C30 | 0.3 (4) |
C5—C1—C9—C10 | −1.7 (3) | C31—C30—C29—C28 | −1.5 (4) |
C2—C1—C9—C10 | 107.5 (2) | C36—C35—C34—C33 | 1.6 (4) |
Pd—C1—C9—C10 | −152.53 (17) | C32—C33—C34—C35 | 0.9 (4) |
C5—C1—C9—C11 | 142.0 (2) | O8—C24—C25—C26 | 136.6 (7) |
C2—C1—C9—C11 | −108.9 (2) | O8—C24—C25'—C26' | 143.8 (12) |
Pd—C1—C9—C11 | −8.9 (3) | C5—O2—C6—C7 | 149.7 (3) |
C5—C1—C9—C2 | −109.2 (2) | O2—C6—C7—C8 | 119.3 (6) |
Pd—C1—C9—C2 | 99.97 (17) | C8'—C7'—C6'—O2 | −24.8 (14) |
C12—C2—C9—C1 | 106.53 (19) | C5—O2—C6'—C7' | 167.5 (5) |
C3—C2—C9—C1 | −101.64 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O3 | 0.96 | 2.28 | 2.950 (3) | 126 |
C11—H11C···O8 | 0.96 | 2.36 | 3.305 (3) | 168 |
C21—H21B···O5 | 0.96 | 2.22 | 2.959 (3) | 133 |
C22—H22C···O2 | 0.96 | 2.32 | 3.268 (3) | 170 |
C27—H27···O1 | 0.93 | 2.31 | 3.057 (3) | 137 |
C36—H36···O7 | 0.93 | 2.40 | 3.111 (3) | 134 |
C8—H8A···O5i | 0.93 | 2.57 | 3.370 (6) | 144 |
C24—H24B···O7ii | 0.96 | 2.52 | 3.446 (3) | 161 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x, −y, −z+1. |
Experimental details
| (I143K) | (I205K) |
Crystal data |
Chemical formula | [Pd(C10H8N2)(C26H32O8)] | [Pd(C10H8N2)(C26H32O8)] |
Mr | 735.10 | 735.10 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 143 | 205 |
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) |
V (Å3) | 3401.7 (7) | 1717.4 (4) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.60 | 0.59 |
Crystal size (mm) | 0.44 × 0.17 × 0.04 | 0.44 × 0.17 × 0.04 |
|
Data collection |
Diffractometer | SIEMENS SMART diffractometer | SIEMENS SMART diffractometer |
Absorption correction | Numerical (SHELXTL; Sheldrick, 1996) | Numerical (SHELXTL; Sheldrick, 1996) |
Tmin, Tmax | 0.817, 0.977 | 0.791, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 64204, 22046, 16183 | 31971, 10543, 8751 |
Rint | 0.059 | 0.070 |
(sin θ/λ)max (Å−1) | 0.750 | 0.729 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.101, 1.21 | 0.042, 0.101, 1.31 |
No. of reflections | 22046 | 10543 |
No. of parameters | 856 | 451 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.61 | 0.56, −0.55 |
Hydrogen-bond geometry (Å, º) for (I143K) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O3 | 0.96 | 2.22 | 2.916 (3) | 128 |
C11—H11C···O8 | 0.96 | 2.30 | 3.255 (3) | 173 |
C21—H21B···O5 | 0.96 | 2.26 | 3.016 (3) | 135 |
C22—H22C···O2 | 0.96 | 2.40 | 3.358 (3) | 176 |
C27—H27···O1 | 0.93 | 2.33 | 3.093 (3) | 139 |
C36—H36···O7 | 0.93 | 2.41 | 3.105 (3) | 132 |
C46—H46C···O11 | 0.96 | 2.28 | 2.982 (3) | 129 |
C47—H47B···O16 | 0.96 | 2.35 | 3.297 (3) | 171 |
C57—H57C···O13 | 0.96 | 2.25 | 2.979 (3) | 132 |
C58—H58B···O10 | 0.96 | 2.34 | 3.286 (3) | 168 |
C63—H63···O9 | 0.93 | 2.28 | 2.974 (3) | 131 |
C72—H72···O15 | 0.93 | 2.39 | 3.182 (3) | 143 |
C8—H8A···O13i | 0.93 | 2.57 | 3.346 (3) | 141 |
C19—H19B···O9ii | 0.93 | 2.53 | 3.397 (3) | 156 |
C24—H24B···O7iii | 0.97 | 2.58 | 3.483 (3) | 156 |
C60—H60A···O15iv | 0.97 | 2.46 | 3.392 (3) | 161 |
Symmetry codes: (i) −x−1, −y, −z+1; (ii) x+1, y, z; (iii) −x, −y−1, −z; (iv) −x−1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) for (I205K) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O3 | 0.96 | 2.28 | 2.950 (3) | 126 |
C11—H11C···O8 | 0.96 | 2.36 | 3.305 (3) | 168 |
C21—H21B···O5 | 0.96 | 2.22 | 2.959 (3) | 133 |
C22—H22C···O2 | 0.96 | 2.32 | 3.268 (3) | 170 |
C27—H27···O1 | 0.93 | 2.31 | 3.057 (3) | 137 |
C36—H36···O7 | 0.93 | 2.40 | 3.111 (3) | 134 |
C8—H8A···O5i | 0.93 | 2.57 | 3.370 (6) | 144 |
C24—H24B···O7ii | 0.96 | 2.52 | 3.446 (3) | 161 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x, −y, −z+1. |
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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.