A new type of α-diketone palladium(II) complex containing a tertiary phosphine, namely the title compound, [Pd(C7H5O2)2(C18H33P)], crystallizes with a square-planar geometry about the palladium(II) metal centre. One tropolonate ligand is bonded in a bidentate chelating mode, while the second one is bonded through a single O atom to the palladium(II) metal centre. The Pd—O distances range from 1.9907 (13) to 2.0702 (12) Å, and the O—Pd—O bite angle for the bidentate tropolonate ligand is 80.30 (5)°.
Supporting information
CCDC reference: 601149
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.024
- wR factor = 0.078
- Data-to-parameter ratio = 21.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C25 - C26 .. 5.09 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXL97.
(Tricyclohexylphosphine)bis(tropolonato)palladium(II)
top
Crystal data top
[Pd(C7H5O2)2(C18H33P)] | F(000) = 2624 |
Mr = 629.05 | Dx = 1.396 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 7765 reflections |
a = 17.6699 (4) Å | θ = 2.5–28.2° |
b = 27.7962 (6) Å | µ = 0.71 mm−1 |
c = 12.2289 (2) Å | T = 293 K |
β = 94.523 (1)° | Plate, red |
V = 5987.6 (2) Å3 | 0.37 × 0.31 × 0.10 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 7406 independent reflections |
Radiation source: fine-focus sealed tube | 6361 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 512 pixels mm-1 | θmax = 28.3°, θmin = 1.4° |
ω scans | h = −23→23 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −37→37 |
Tmin = 0.776, Tmax = 0.936 | l = −16→16 |
81120 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.039P)2 + 3.4366P] where P = (Fo2 + 2Fc2)/3 |
7406 reflections | (Δ/σ)max = 0.001 |
343 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | |
Pd | 0.225287 (8) | 0.076091 (5) | 0.012278 (10) | 0.03988 (5) | |
P | 0.28918 (3) | 0.113052 (15) | −0.11405 (4) | 0.03759 (10) | |
O22 | 0.27297 (8) | 0.11889 (5) | 0.13139 (12) | 0.0554 (3) | |
O11 | 0.16169 (8) | 0.03653 (5) | 0.11540 (10) | 0.0507 (3) | |
O12 | 0.18487 (8) | 0.02561 (5) | −0.09205 (11) | 0.0514 (3) | |
C23 | 0.27523 (15) | 0.14315 (9) | 0.30952 (18) | 0.0623 (5) | |
H23 | 0.3207 | 0.1262 | 0.3163 | 0.075* | |
C31 | 0.30867 (11) | 0.07000 (6) | −0.22300 (15) | 0.0425 (4) | |
H31 | 0.2601 | 0.0541 | −0.2433 | 0.051* | |
C41 | 0.23223 (10) | 0.16110 (6) | −0.18396 (15) | 0.0420 (4) | |
H41 | 0.2575 | 0.1703 | −0.2493 | 0.050* | |
C51 | 0.37512 (10) | 0.14374 (7) | −0.05460 (16) | 0.0434 (4) | |
H51 | 0.3559 | 0.1685 | −0.0068 | 0.052* | |
C46 | 0.22538 (12) | 0.20635 (7) | −0.11430 (18) | 0.0504 (4) | |
H46A | 0.2023 | 0.1981 | −0.0474 | 0.061* | |
H46B | 0.2756 | 0.2192 | −0.0942 | 0.061* | |
C42 | 0.15294 (12) | 0.14200 (8) | −0.22281 (19) | 0.0543 (5) | |
H42A | 0.1581 | 0.1144 | −0.2703 | 0.065* | |
H42B | 0.1271 | 0.1315 | −0.1599 | 0.065* | |
C45 | 0.17756 (13) | 0.24417 (7) | −0.1770 (2) | 0.0629 (6) | |
H45A | 0.1721 | 0.2719 | −0.1301 | 0.076* | |
H45B | 0.2034 | 0.2546 | −0.2400 | 0.076* | |
C32 | 0.36204 (14) | 0.03011 (8) | −0.18048 (17) | 0.0563 (5) | |
H32A | 0.3420 | 0.0151 | −0.1173 | 0.068* | |
H32B | 0.4111 | 0.0438 | −0.1571 | 0.068* | |
C52 | 0.41996 (13) | 0.17197 (9) | −0.13527 (19) | 0.0620 (6) | |
H52A | 0.4464 | 0.1498 | −0.1803 | 0.074* | |
H52B | 0.3855 | 0.1911 | −0.1832 | 0.074* | |
C43 | 0.10569 (14) | 0.18056 (9) | −0.2846 (2) | 0.0668 (6) | |
H43A | 0.1288 | 0.1887 | −0.3516 | 0.080* | |
H43B | 0.0552 | 0.1681 | −0.3047 | 0.080* | |
C36 | 0.33357 (17) | 0.09144 (8) | −0.32936 (18) | 0.0635 (6) | |
H36A | 0.2959 | 0.1145 | −0.3581 | 0.076* | |
H36B | 0.3812 | 0.1084 | −0.3142 | 0.076* | |
C35 | 0.34336 (16) | 0.05264 (8) | −0.41495 (18) | 0.0652 (6) | |
H35A | 0.2945 | 0.0380 | −0.4361 | 0.078* | |
H35B | 0.3621 | 0.0671 | −0.4798 | 0.078* | |
C56 | 0.42883 (12) | 0.11367 (8) | 0.02197 (19) | 0.0565 (5) | |
H56A | 0.4000 | 0.0963 | 0.0734 | 0.068* | |
H56B | 0.4551 | 0.0904 | −0.0204 | 0.068* | |
C55 | 0.48633 (14) | 0.14642 (10) | 0.0843 (2) | 0.0720 (7) | |
H55A | 0.4601 | 0.1673 | 0.1323 | 0.086* | |
H55B | 0.5219 | 0.1269 | 0.1297 | 0.086* | |
C34 | 0.39785 (17) | 0.01457 (10) | −0.3714 (2) | 0.0760 (7) | |
H34A | 0.4477 | 0.0287 | −0.3558 | 0.091* | |
H34B | 0.4018 | −0.0102 | −0.4266 | 0.091* | |
C44 | 0.09989 (14) | 0.22538 (9) | −0.2154 (2) | 0.0695 (6) | |
H44A | 0.0721 | 0.2500 | −0.2582 | 0.083* | |
H44B | 0.0719 | 0.2180 | −0.1523 | 0.083* | |
C53 | 0.47706 (16) | 0.20473 (11) | −0.0719 (3) | 0.0829 (8) | |
H53A | 0.5067 | 0.2217 | −0.1232 | 0.099* | |
H53B | 0.4500 | 0.2285 | −0.0320 | 0.099* | |
C33 | 0.37191 (18) | −0.00788 (9) | −0.2680 (2) | 0.0745 (7) | |
H33A | 0.4090 | −0.0315 | −0.2400 | 0.089* | |
H33B | 0.3241 | −0.0244 | −0.2849 | 0.089* | |
C54 | 0.52977 (14) | 0.17687 (11) | 0.0076 (3) | 0.0844 (9) | |
H54A | 0.5623 | 0.1992 | 0.0504 | 0.101* | |
H54B | 0.5618 | 0.1562 | −0.0329 | 0.101* | |
C11 | 0.12560 (10) | 0.00205 (6) | 0.06473 (15) | 0.0422 (4) | |
C12 | 0.14154 (10) | −0.00585 (6) | −0.04932 (15) | 0.0417 (4) | |
C14 | 0.06326 (16) | −0.07991 (7) | −0.0982 (2) | 0.0637 (6) | |
H14 | 0.0542 | −0.1015 | −0.1558 | 0.076* | |
C17 | 0.07349 (12) | −0.02474 (8) | 0.12077 (17) | 0.0543 (5) | |
H17 | 0.0693 | −0.0150 | 0.1928 | 0.065* | |
C13 | 0.11644 (13) | −0.04435 (7) | −0.11538 (17) | 0.0530 (5) | |
H13 | 0.1388 | −0.0467 | −0.1815 | 0.064* | |
C15 | 0.02210 (14) | −0.08803 (8) | −0.0094 (2) | 0.0658 (6) | |
H15 | −0.0130 | −0.1130 | −0.0156 | 0.079* | |
C16 | 0.02750 (13) | −0.06282 (8) | 0.0880 (2) | 0.0604 (5) | |
H16 | −0.0050 | −0.0732 | 0.1395 | 0.073* | |
O21 | 0.13291 (10) | 0.15127 (7) | 0.07903 (16) | 0.0750 (5) | |
C21 | 0.16076 (12) | 0.15915 (7) | 0.17335 (19) | 0.0538 (5) | |
C22 | 0.23671 (11) | 0.13988 (7) | 0.20575 (16) | 0.0456 (4) | |
C27 | 0.12030 (18) | 0.18813 (11) | 0.2465 (3) | 0.0901 (9) | |
H27 | 0.0736 | 0.1990 | 0.2157 | 0.108* | |
C24 | 0.25869 (19) | 0.16686 (12) | 0.4045 (2) | 0.0840 (8) | |
H24 | 0.2946 | 0.1631 | 0.4637 | 0.101* | |
C25 | 0.1991 (2) | 0.19419 (14) | 0.4240 (3) | 0.1032 (11) | |
H25 | 0.2000 | 0.2087 | 0.4926 | 0.124* | |
C26 | 0.1369 (2) | 0.20300 (13) | 0.3530 (3) | 0.1124 (13) | |
H26 | 0.0998 | 0.2221 | 0.3812 | 0.135* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd | 0.04391 (9) | 0.04047 (8) | 0.03628 (8) | −0.00695 (5) | 0.00954 (5) | −0.00273 (5) |
P | 0.0390 (2) | 0.0357 (2) | 0.0388 (2) | −0.00401 (17) | 0.00786 (17) | −0.00064 (16) |
O22 | 0.0474 (7) | 0.0665 (9) | 0.0536 (8) | −0.0110 (7) | 0.0116 (6) | −0.0192 (7) |
O11 | 0.0607 (8) | 0.0551 (8) | 0.0378 (6) | −0.0183 (6) | 0.0131 (6) | −0.0046 (6) |
O12 | 0.0650 (9) | 0.0514 (7) | 0.0395 (7) | −0.0181 (6) | 0.0142 (6) | −0.0054 (5) |
C23 | 0.0694 (14) | 0.0668 (14) | 0.0508 (12) | −0.0007 (11) | 0.0056 (10) | −0.0026 (10) |
C31 | 0.0484 (10) | 0.0406 (9) | 0.0397 (9) | −0.0035 (7) | 0.0098 (7) | −0.0022 (7) |
C41 | 0.0423 (9) | 0.0401 (9) | 0.0442 (9) | −0.0024 (7) | 0.0067 (7) | 0.0011 (7) |
C51 | 0.0391 (9) | 0.0435 (9) | 0.0482 (10) | −0.0049 (7) | 0.0063 (7) | −0.0048 (7) |
C46 | 0.0511 (11) | 0.0409 (9) | 0.0589 (12) | −0.0026 (8) | 0.0022 (9) | −0.0045 (8) |
C42 | 0.0472 (11) | 0.0514 (11) | 0.0629 (12) | −0.0017 (8) | −0.0033 (9) | −0.0104 (9) |
C45 | 0.0637 (13) | 0.0419 (10) | 0.0830 (16) | 0.0042 (10) | 0.0043 (11) | 0.0018 (10) |
C32 | 0.0699 (14) | 0.0515 (11) | 0.0471 (10) | 0.0112 (10) | 0.0027 (9) | −0.0050 (9) |
C52 | 0.0519 (12) | 0.0732 (14) | 0.0618 (13) | −0.0234 (10) | 0.0108 (10) | −0.0007 (11) |
C43 | 0.0570 (13) | 0.0743 (15) | 0.0667 (14) | 0.0094 (11) | −0.0097 (11) | −0.0073 (12) |
C36 | 0.0987 (19) | 0.0485 (11) | 0.0470 (11) | −0.0027 (11) | 0.0286 (12) | −0.0005 (9) |
C35 | 0.0924 (18) | 0.0595 (13) | 0.0454 (11) | −0.0051 (12) | 0.0159 (11) | −0.0093 (9) |
C56 | 0.0495 (11) | 0.0586 (12) | 0.0606 (12) | 0.0054 (9) | −0.0008 (9) | −0.0062 (10) |
C55 | 0.0586 (14) | 0.0870 (17) | 0.0678 (15) | 0.0098 (12) | −0.0123 (11) | −0.0240 (13) |
C34 | 0.0868 (18) | 0.0785 (17) | 0.0637 (15) | 0.0119 (14) | 0.0129 (13) | −0.0304 (13) |
C44 | 0.0590 (13) | 0.0610 (13) | 0.0867 (17) | 0.0146 (11) | −0.0051 (12) | −0.0037 (12) |
C53 | 0.0660 (16) | 0.0876 (19) | 0.096 (2) | −0.0387 (14) | 0.0107 (14) | −0.0105 (15) |
C33 | 0.105 (2) | 0.0507 (12) | 0.0664 (15) | 0.0198 (13) | −0.0002 (14) | −0.0129 (11) |
C54 | 0.0494 (13) | 0.107 (2) | 0.097 (2) | −0.0202 (14) | 0.0021 (13) | −0.0393 (17) |
C11 | 0.0436 (9) | 0.0427 (9) | 0.0406 (9) | −0.0017 (7) | 0.0063 (7) | 0.0032 (7) |
C12 | 0.0434 (9) | 0.0394 (8) | 0.0426 (9) | −0.0017 (7) | 0.0047 (7) | 0.0016 (7) |
C14 | 0.0792 (16) | 0.0430 (11) | 0.0674 (15) | −0.0130 (10) | −0.0046 (12) | −0.0061 (9) |
C17 | 0.0569 (12) | 0.0585 (12) | 0.0488 (11) | −0.0122 (9) | 0.0126 (9) | 0.0046 (9) |
C13 | 0.0659 (13) | 0.0454 (10) | 0.0478 (10) | −0.0029 (9) | 0.0049 (9) | −0.0034 (8) |
C15 | 0.0634 (14) | 0.0503 (11) | 0.0823 (17) | −0.0179 (10) | −0.0037 (12) | 0.0077 (11) |
C16 | 0.0546 (12) | 0.0602 (12) | 0.0672 (14) | −0.0143 (10) | 0.0095 (10) | 0.0132 (11) |
O21 | 0.0563 (10) | 0.0895 (13) | 0.0778 (12) | −0.0053 (9) | −0.0032 (8) | 0.0012 (10) |
C21 | 0.0538 (11) | 0.0491 (11) | 0.0597 (12) | −0.0041 (9) | 0.0122 (9) | 0.0048 (9) |
C22 | 0.0502 (10) | 0.0412 (9) | 0.0468 (10) | −0.0108 (8) | 0.0134 (8) | −0.0041 (7) |
C27 | 0.0801 (19) | 0.089 (2) | 0.104 (2) | 0.0340 (16) | 0.0229 (17) | 0.0016 (17) |
C24 | 0.099 (2) | 0.103 (2) | 0.0507 (14) | −0.0107 (17) | 0.0087 (13) | −0.0091 (14) |
C25 | 0.126 (3) | 0.120 (3) | 0.0678 (19) | 0.002 (2) | 0.033 (2) | −0.0253 (18) |
C26 | 0.124 (3) | 0.105 (3) | 0.115 (3) | 0.040 (2) | 0.051 (2) | −0.031 (2) |
Geometric parameters (Å, º) top
Pd—O12 | 1.9907 (13) | C35—C34 | 1.500 (4) |
Pd—O22 | 2.0132 (13) | C35—H35A | 0.9700 |
Pd—O11 | 2.0702 (12) | C35—H35B | 0.9700 |
Pd—P | 2.2342 (4) | C56—C55 | 1.523 (3) |
P—C51 | 1.8407 (18) | C56—H56A | 0.9700 |
P—C41 | 1.8417 (19) | C56—H56B | 0.9700 |
P—C31 | 1.8434 (18) | C55—C54 | 1.517 (4) |
O22—C22 | 1.292 (2) | C55—H55A | 0.9700 |
O11—C11 | 1.283 (2) | C55—H55B | 0.9700 |
O12—C12 | 1.299 (2) | C34—C33 | 1.514 (4) |
C23—C24 | 1.387 (3) | C34—H34A | 0.9700 |
C23—C22 | 1.395 (3) | C34—H34B | 0.9700 |
C23—H23 | 0.9300 | C44—H44A | 0.9700 |
C31—C32 | 1.520 (3) | C44—H44B | 0.9700 |
C31—C36 | 1.527 (3) | C53—C54 | 1.507 (4) |
C31—H31 | 0.9800 | C53—H53A | 0.9700 |
C41—C46 | 1.529 (3) | C53—H53B | 0.9700 |
C41—C42 | 1.538 (3) | C33—H33A | 0.9700 |
C41—H41 | 0.9800 | C33—H33B | 0.9700 |
C51—C56 | 1.528 (3) | C54—H54A | 0.9700 |
C51—C52 | 1.530 (3) | C54—H54B | 0.9700 |
C51—H51 | 0.9800 | C11—C17 | 1.404 (3) |
C46—C45 | 1.518 (3) | C11—C12 | 1.461 (2) |
C46—H46A | 0.9700 | C12—C13 | 1.392 (3) |
C46—H46B | 0.9700 | C14—C15 | 1.372 (4) |
C42—C43 | 1.523 (3) | C14—C13 | 1.391 (3) |
C42—H42A | 0.9700 | C14—H14 | 0.9300 |
C42—H42B | 0.9700 | C17—C16 | 1.375 (3) |
C45—C44 | 1.508 (3) | C17—H17 | 0.9300 |
C45—H45A | 0.9700 | C13—H13 | 0.9300 |
C45—H45B | 0.9700 | C15—C16 | 1.379 (4) |
C32—C33 | 1.523 (3) | C15—H15 | 0.9300 |
C32—H32A | 0.9700 | C16—H16 | 0.9300 |
C32—H32B | 0.9700 | O21—C21 | 1.237 (3) |
C52—C53 | 1.525 (3) | C21—C27 | 1.435 (3) |
C52—H52A | 0.9700 | C21—C22 | 1.470 (3) |
C52—H52B | 0.9700 | C27—C26 | 1.376 (5) |
C43—C44 | 1.514 (3) | C27—H27 | 0.9300 |
C43—H43A | 0.9700 | C24—C25 | 1.335 (5) |
C43—H43B | 0.9700 | C24—H24 | 0.9300 |
C36—C35 | 1.522 (3) | C25—C26 | 1.369 (5) |
C36—H36A | 0.9700 | C25—H25 | 0.9300 |
C36—H36B | 0.9700 | C26—H26 | 0.9300 |
| | | |
O12—Pd—O22 | 171.38 (6) | H35A—C35—H35B | 108.0 |
O12—Pd—O11 | 80.30 (5) | C55—C56—C51 | 109.71 (18) |
O22—Pd—O11 | 95.13 (5) | C55—C56—H56A | 109.7 |
O12—Pd—P | 93.23 (4) | C51—C56—H56A | 109.7 |
O22—Pd—P | 91.32 (4) | C55—C56—H56B | 109.7 |
O11—Pd—P | 173.52 (4) | C51—C56—H56B | 109.7 |
C51—P—C41 | 104.52 (8) | H56A—C56—H56B | 108.2 |
C51—P—C31 | 113.01 (9) | C54—C55—C56 | 112.0 (2) |
C41—P—C31 | 105.17 (8) | C54—C55—H55A | 109.2 |
C51—P—Pd | 112.72 (6) | C56—C55—H55A | 109.2 |
C41—P—Pd | 111.53 (6) | C54—C55—H55B | 109.2 |
C31—P—Pd | 109.55 (6) | C56—C55—H55B | 109.2 |
C22—O22—Pd | 125.00 (12) | H55A—C55—H55B | 107.9 |
C11—O11—Pd | 112.06 (11) | C35—C34—C33 | 111.1 (2) |
C12—O12—Pd | 114.19 (11) | C35—C34—H34A | 109.4 |
C24—C23—C22 | 132.3 (3) | C33—C34—H34A | 109.4 |
C24—C23—H23 | 113.8 | C35—C34—H34B | 109.4 |
C22—C23—H23 | 113.8 | C33—C34—H34B | 109.4 |
C32—C31—C36 | 111.31 (18) | H34A—C34—H34B | 108.0 |
C32—C31—P | 111.86 (13) | C45—C44—C43 | 111.0 (2) |
C36—C31—P | 116.44 (13) | C45—C44—H44A | 109.4 |
C32—C31—H31 | 105.4 | C43—C44—H44A | 109.4 |
C36—C31—H31 | 105.4 | C45—C44—H44B | 109.4 |
P—C31—H31 | 105.4 | C43—C44—H44B | 109.4 |
C46—C41—C42 | 110.23 (16) | H44A—C44—H44B | 108.0 |
C46—C41—P | 113.72 (13) | C54—C53—C52 | 111.8 (2) |
C42—C41—P | 110.13 (13) | C54—C53—H53A | 109.3 |
C46—C41—H41 | 107.5 | C52—C53—H53A | 109.3 |
C42—C41—H41 | 107.5 | C54—C53—H53B | 109.3 |
P—C41—H41 | 107.5 | C52—C53—H53B | 109.3 |
C56—C51—C52 | 110.33 (17) | H53A—C53—H53B | 107.9 |
C56—C51—P | 116.20 (13) | C34—C33—C32 | 111.1 (2) |
C52—C51—P | 115.86 (14) | C34—C33—H33A | 109.4 |
C56—C51—H51 | 104.3 | C32—C33—H33A | 109.4 |
C52—C51—H51 | 104.3 | C34—C33—H33B | 109.4 |
P—C51—H51 | 104.3 | C32—C33—H33B | 109.4 |
C45—C46—C41 | 110.70 (18) | H33A—C33—H33B | 108.0 |
C45—C46—H46A | 109.5 | C53—C54—C55 | 111.6 (2) |
C41—C46—H46A | 109.5 | C53—C54—H54A | 109.3 |
C45—C46—H46B | 109.5 | C55—C54—H54A | 109.3 |
C41—C46—H46B | 109.5 | C53—C54—H54B | 109.3 |
H46A—C46—H46B | 108.1 | C55—C54—H54B | 109.3 |
C43—C42—C41 | 111.16 (18) | H54A—C54—H54B | 108.0 |
C43—C42—H42A | 109.4 | O11—C11—C17 | 118.72 (17) |
C41—C42—H42A | 109.4 | O11—C11—C12 | 116.57 (15) |
C43—C42—H42B | 109.4 | C17—C11—C12 | 124.70 (17) |
C41—C42—H42B | 109.4 | O12—C12—C13 | 117.06 (17) |
H42A—C42—H42B | 108.0 | O12—C12—C11 | 116.55 (15) |
C44—C45—C46 | 111.97 (18) | C13—C12—C11 | 126.36 (17) |
C44—C45—H45A | 109.2 | C15—C14—C13 | 130.0 (2) |
C46—C45—H45A | 109.2 | C15—C14—H14 | 115.0 |
C44—C45—H45B | 109.2 | C13—C14—H14 | 115.0 |
C46—C45—H45B | 109.2 | C16—C17—C11 | 131.4 (2) |
H45A—C45—H45B | 107.9 | C16—C17—H17 | 114.3 |
C31—C32—C33 | 111.58 (18) | C11—C17—H17 | 114.3 |
C31—C32—H32A | 109.3 | C14—C13—C12 | 130.3 (2) |
C33—C32—H32A | 109.3 | C14—C13—H13 | 114.9 |
C31—C32—H32B | 109.3 | C12—C13—H13 | 114.9 |
C33—C32—H32B | 109.3 | C14—C15—C16 | 126.5 (2) |
H32A—C32—H32B | 108.0 | C14—C15—H15 | 116.7 |
C53—C52—C51 | 109.5 (2) | C16—C15—H15 | 116.7 |
C53—C52—H52A | 109.8 | C17—C16—C15 | 130.0 (2) |
C51—C52—H52A | 109.8 | C17—C16—H16 | 115.0 |
C53—C52—H52B | 109.8 | C15—C16—H16 | 115.0 |
C51—C52—H52B | 109.8 | O21—C21—C27 | 119.9 (2) |
H52A—C52—H52B | 108.2 | O21—C21—C22 | 118.3 (2) |
C44—C43—C42 | 111.1 (2) | C27—C21—C22 | 121.7 (2) |
C44—C43—H43A | 109.4 | O22—C22—C23 | 115.87 (19) |
C42—C43—H43A | 109.4 | O22—C22—C21 | 117.88 (18) |
C44—C43—H43B | 109.4 | C23—C22—C21 | 126.23 (19) |
C42—C43—H43B | 109.4 | C26—C27—C21 | 132.8 (3) |
H43A—C43—H43B | 108.0 | C26—C27—H27 | 113.6 |
C35—C36—C31 | 111.43 (18) | C21—C27—H27 | 113.6 |
C35—C36—H36A | 109.3 | C25—C24—C23 | 129.9 (3) |
C31—C36—H36A | 109.3 | C25—C24—H24 | 115.1 |
C35—C36—H36B | 109.3 | C23—C24—H24 | 115.1 |
C31—C36—H36B | 109.3 | C24—C25—C26 | 126.5 (3) |
H36A—C36—H36B | 108.0 | C24—C25—H25 | 116.8 |
C34—C35—C36 | 111.1 (2) | C26—C25—H25 | 116.8 |
C34—C35—H35A | 109.4 | C25—C26—C27 | 130.3 (3) |
C36—C35—H35A | 109.4 | C25—C26—H26 | 114.8 |
C34—C35—H35B | 109.4 | C27—C26—H26 | 114.8 |
C36—C35—H35B | 109.4 | | |
| | | |
O12—Pd—P—C51 | −150.45 (8) | C31—C36—C35—C34 | −55.7 (3) |
O22—Pd—P—C51 | 22.23 (8) | C52—C51—C56—C55 | 58.6 (2) |
O12—Pd—P—C41 | 92.33 (8) | P—C51—C56—C55 | −166.90 (16) |
O22—Pd—P—C41 | −95.00 (8) | C51—C56—C55—C54 | −55.8 (3) |
O12—Pd—P—C31 | −23.69 (8) | C36—C35—C34—C33 | 57.3 (3) |
O22—Pd—P—C31 | 148.99 (8) | C46—C45—C44—C43 | −56.2 (3) |
O11—Pd—O22—C22 | −46.33 (17) | C42—C43—C44—C45 | 55.7 (3) |
P—Pd—O22—C22 | 134.25 (16) | C51—C52—C53—C54 | 56.8 (3) |
O12—Pd—O11—C11 | −3.27 (13) | C35—C34—C33—C32 | −56.9 (3) |
O22—Pd—O11—C11 | −175.89 (13) | C31—C32—C33—C34 | 54.9 (3) |
O11—Pd—O12—C12 | −0.32 (13) | C52—C53—C54—C55 | −54.3 (3) |
P—Pd—O12—C12 | 179.93 (13) | C56—C55—C54—C53 | 53.9 (3) |
C51—P—C31—C32 | 61.10 (16) | Pd—O11—C11—C17 | −173.10 (15) |
C41—P—C31—C32 | 174.52 (14) | Pd—O11—C11—C12 | 6.0 (2) |
Pd—P—C31—C32 | −65.49 (15) | Pd—O12—C12—C13 | −174.89 (14) |
C51—P—C31—C36 | −68.45 (19) | Pd—O12—C12—C11 | 3.5 (2) |
C41—P—C31—C36 | 44.97 (19) | O11—C11—C12—O12 | −6.6 (3) |
Pd—P—C31—C36 | 164.96 (16) | C17—C11—C12—O12 | 172.42 (18) |
C51—P—C41—C46 | −47.13 (15) | O11—C11—C12—C13 | 171.62 (19) |
C31—P—C41—C46 | −166.39 (14) | C17—C11—C12—C13 | −9.3 (3) |
Pd—P—C41—C46 | 74.94 (14) | O11—C11—C17—C16 | 179.8 (2) |
C51—P—C41—C42 | −171.42 (13) | C12—C11—C17—C16 | 0.8 (4) |
C31—P—C41—C42 | 69.33 (15) | C15—C14—C13—C12 | −2.3 (5) |
Pd—P—C41—C42 | −49.34 (14) | O12—C12—C13—C14 | −171.3 (2) |
C41—P—C51—C56 | 172.16 (15) | C11—C12—C13—C14 | 10.4 (4) |
C31—P—C51—C56 | −74.03 (16) | C13—C14—C15—C16 | −3.3 (5) |
Pd—P—C51—C56 | 50.86 (16) | C11—C17—C16—C15 | 4.1 (5) |
C41—P—C51—C52 | −55.86 (17) | C14—C15—C16—C17 | −0.2 (5) |
C31—P—C51—C52 | 57.95 (18) | Pd—O22—C22—C23 | 143.55 (16) |
Pd—P—C51—C52 | −177.16 (14) | Pd—O22—C22—C21 | −38.2 (2) |
C42—C41—C46—C45 | −55.6 (2) | C24—C23—C22—O22 | 172.3 (3) |
P—C41—C46—C45 | −179.79 (14) | C24—C23—C22—C21 | −5.7 (4) |
C46—C41—C42—C43 | 55.8 (2) | O21—C21—C22—O22 | 5.3 (3) |
P—C41—C42—C43 | −177.90 (15) | C27—C21—C22—O22 | −172.1 (2) |
C41—C46—C45—C44 | 56.4 (3) | O21—C21—C22—C23 | −176.7 (2) |
C36—C31—C32—C33 | −53.3 (3) | C27—C21—C22—C23 | 5.9 (3) |
P—C31—C32—C33 | 174.54 (18) | O21—C21—C27—C26 | −179.4 (4) |
C56—C51—C52—C53 | −59.0 (3) | C22—C21—C27—C26 | −2.0 (5) |
P—C51—C52—C53 | 166.32 (18) | C22—C23—C24—C25 | 0.0 (6) |
C41—C42—C43—C44 | −56.0 (3) | C23—C24—C25—C26 | 3.9 (7) |
C32—C31—C36—C35 | 53.5 (3) | C24—C25—C26—C27 | −2.1 (8) |
P—C31—C36—C35 | −176.64 (18) | C21—C27—C26—C25 | −0.2 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C46—H46A···O21 | 0.97 | 2.43 | 3.348 (3) | 159 |
C13—H13···O11i | 0.93 | 2.56 | 3.456 (2) | 161 |
C15—H15···O21ii | 0.93 | 2.44 | 3.309 (3) | 155 |
Symmetry codes: (i) x, −y, z−1/2; (ii) −x, −y, −z. |