(Tricyclo­hexyl­phosphine)bis­(tropolonato)palladium(II)

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)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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)

Crystal data

[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) Å^3	0.37 × 0.31 × 0.10 mm
Z = 8

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 3.4366P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O11^i	0.93	2.56	3.456 (2)	161
C15—H15···O21^ii	0.93	2.44	3.309 (3)	155

Symmetry codes: (i) x, −y, z−1/2; (ii) −x, −y, −z.