π-Stacking of μ-3,3′-bis­acetyl­acetonato-bis­[(2,2′-bipyri­dine)palladium(II)] hexa­fluoro­phosphate acetonitrile solvate

Mei, G.-Q.; Huang, K.-L.; Huang, H.-P.; Li, Y.-Z.

doi:10.1107/S1600536806033861

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π-Stacking of μ-3,3′-bisacetylacetonato-bis[(2,2′-bipyridine)palladium(II)] hexafluorophosphate acetonitrile solvate

G.-Q. Mei, K.-L. Huang, H.-P. Huang and Y.-Z. Li

In the title complex, [Pd₂(C₁₀H₁₂O₄)₂(C₁₀H₈N₂)₂](PF₆)₂·CH₃CN, the Pd^II centers have a distorted cis-square-planar geometry defined by an O,O′-bidentate bisacetylacetonate dianion ligand and a chelating 2,2′-bipyridine ligand. The crystal structure is stabilized by electrostatic forces between the cations and anions, intermolecular π–π stacking interactions between pairs of 2,2′-bipyridine rings, and weak intermolecular hydrogen bonds involving hexafluorophosphate anions (C—H

F) and the solvent acetonitrile molecules (C—H

N).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033861/ng2048sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033861/ng2048Isup2.hkl Contains datablock I

CCDC reference: 621418

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
R factor = 0.060
wR factor = 0.141
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level A
CHEMW01_ALERT_1_A  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.90 <> 1.10
            Calculated formula weight =  1248.5587
            Formula weight given      =  1052.3600

Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     1.123
            Value of mu given      =     1.097
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P2
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C42 H43 F12 N5 O8 P2 Pd2
            Atom count from the _atom_site data:  C32 H31 F12 N5 O4 P2 Pd2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C42 H43 F12 N5 O8 P2 Pd2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        336.00    256.00   80.00
           H        344.00    248.00   96.00
           F         96.00     96.00    0.00
           N         40.00     40.00    0.00
           O         64.00     32.00   32.00
           P         16.00     16.00    0.00
           Pd        16.00     16.00    0.00

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

µ-3,3'-bisacetylacetonato-bis[(2,2'-bipyridine)palladium(II)] hexafluorophosphate acetonitrile solvate top

Crystal data top

[Pd₂(C₁₀H₁₂O₄)₂(C₁₀H₈N₂)₂](PF₆)₂·C₂H₃N	F(000) = 4160
M_r = 1052.36	D_x = 1.779 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3384 reflections
a = 22.070 (4) Å	θ = 0.9–27.5°
b = 16.104 (3) Å	µ = 1.10 mm⁻¹
c = 23.479 (5) Å	T = 298 K
β = 109.70 (3)°	Block, yellow
V = 7856 (3) Å³	0.30 × 0.30 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	8574 independent reflections
Radiation source: sealed tube	6165 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −27→28
T_min = 0.73, T_max = 0.81	k = 0→20
16272 measured reflections	l = −29→28

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0717P)²] where P = (F_o² + 2F_c²)/3
8574 reflections	(Δ/σ)_max = 0.001
521 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −1.06 e Å⁻³

Special details top

Experimental. 1H NMR (400?MHz, [D3]Acetonitrile): δ 2.21 (12H, s, CH3), 7.82 (4H, t, J = 8.5 Hz, bpy-H4,4'), 8.34 (8H, m, bpy-H3,3' and bpy-H5,5'), 8.70 (4H, d, J = 5.6 Hz, bpy-H6,6') p.p.m.

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	U_iso*/U_eq
C1	0.9399 (3)	−0.1265 (3)	0.4121 (3)	0.0546 (13)
H1	0.9203	−0.1275	0.3702	0.065*
C2	0.9889 (3)	−0.1818 (3)	0.4393 (3)	0.0521 (13)
H2	1.0028	−0.2190	0.4160	0.063*
C3	1.0169 (3)	−0.1814 (4)	0.5009 (3)	0.0522 (13)
H3	1.0500	−0.2182	0.5199	0.063*
C4	0.9956 (3)	−0.1260 (3)	0.5346 (3)	0.0541 (13)
H4	1.0141	−0.1255	0.5765	0.065*
C5	0.9470 (2)	−0.0713 (3)	0.5060 (3)	0.0479 (12)
C6	0.9202 (2)	−0.0095 (3)	0.5372 (2)	0.0468 (11)
C7	0.9407 (3)	0.0036 (4)	0.5989 (2)	0.0533 (13)
H7	0.9745	−0.0275	0.6245	0.064*
C8	0.9114 (3)	0.0621 (4)	0.6222 (2)	0.0555 (14)
H8	0.9247	0.0705	0.6638	0.067*
C9	0.8621 (3)	0.1089 (4)	0.5845 (3)	0.0590 (14)
H9	0.8417	0.1490	0.6000	0.071*
C10	0.8434 (3)	0.0951 (4)	0.5224 (2)	0.0513 (12)
H10	0.8104	0.1268	0.4964	0.062*
C11	0.8167 (3)	−0.0008 (4)	0.2236 (2)	0.0542 (13)
H11A	0.8428	−0.0500	0.2320	0.081*
H11B	0.8373	0.0413	0.2076	0.081*
H11C	0.7753	−0.0134	0.1945	0.081*
C12	0.8085 (3)	0.0301 (4)	0.2809 (2)	0.0548 (13)
C13	0.7677 (3)	0.0975 (4)	0.2810 (2)	0.0551 (13)
C14	0.7568 (3)	0.1256 (4)	0.3334 (3)	0.0560 (13)
C15	0.7078 (3)	0.1922 (4)	0.3299 (3)	0.0648 (16)
H15A	0.7063	0.2028	0.3696	0.097*
H15B	0.6662	0.1742	0.3038	0.097*
H15C	0.7197	0.2422	0.3139	0.097*
C16	0.8237 (3)	0.2517 (4)	0.2564 (3)	0.0640 (16)
H16A	0.8265	0.3093	0.2471	0.096*
H16B	0.8612	0.2230	0.2548	0.096*
H16C	0.8209	0.2465	0.2961	0.096*
C17	0.7636 (3)	0.2137 (4)	0.2101 (3)	0.0588 (15)
C18	0.7359 (3)	0.1422 (4)	0.2223 (2)	0.0547 (13)
C19	0.6780 (3)	0.1095 (4)	0.1828 (2)	0.0553 (13)
C20	0.6446 (3)	0.0388 (4)	0.2011 (3)	0.0671 (18)
H20A	0.6001	0.0527	0.1926	0.101*
H20B	0.6646	0.0285	0.2436	0.101*
H20C	0.6477	−0.0100	0.1788	0.101*
C21	0.7475 (3)	0.3642 (4)	0.0560 (3)	0.0580 (14)
H21	0.7699	0.3681	0.0973	0.070*
C22	0.7620 (3)	0.4170 (4)	0.0178 (3)	0.0652 (16)
H22	0.7938	0.4569	0.0330	0.078*
C23	0.7301 (3)	0.4119 (5)	−0.0427 (3)	0.0705 (17)
H23	0.7403	0.4476	−0.0693	0.085*
C24	0.6829 (3)	0.3535 (3)	−0.0640 (2)	0.0478 (12)
H24	0.6605	0.3500	−0.1053	0.057*
C25	0.6679 (3)	0.3000 (4)	−0.0252 (2)	0.0519 (13)
C26	0.6182 (3)	0.2378 (4)	−0.0405 (2)	0.0526 (13)
C27	0.5768 (3)	0.2228 (4)	−0.0993 (3)	0.0599 (15)
H27	0.5811	0.2525	−0.1317	0.072*
C28	0.5301 (3)	0.1641 (4)	−0.1086 (3)	0.0649 (16)
H28	0.5018	0.1544	−0.1476	0.078*
C29	0.5242 (3)	0.1181 (4)	−0.0599 (3)	0.0678 (17)
H29	0.4927	0.0777	−0.0654	0.081*
C30	0.5674 (3)	0.1361 (4)	−0.0037 (3)	0.0575 (14)
H30	0.5651	0.1057	0.0293	0.069*
C31	0.8989 (3)	0.4992 (4)	0.1568 (3)	0.0669 (16)
C32	0.9355 (3)	0.5599 (4)	0.1409 (3)	0.0700 (18)
H32A	0.9540	0.5966	0.1745	0.105*
H32B	0.9084	0.5911	0.1070	0.105*
H32C	0.9693	0.5338	0.1302	0.105*
F1	0.7816 (2)	0.3988 (3)	0.4042 (2)	0.0875 (13)
F2	0.9077 (2)	0.3494 (3)	0.5042 (2)	0.0956 (15)
F3	0.8149 (2)	0.4013 (3)	0.50369 (19)	0.0851 (13)
F4	0.8718 (2)	0.3396 (3)	0.40779 (19)	0.0805 (11)
F5	0.8673 (2)	0.4594 (3)	0.4549 (2)	0.0855 (12)
F6	0.8163 (2)	0.2862 (3)	0.4571 (2)	0.0873 (13)
F7	0.5493 (2)	0.2627 (3)	0.3170 (2)	0.1008 (17)
F8	0.5405 (2)	0.1924 (3)	0.2340 (2)	0.0921 (14)
F9	0.5377 (2)	0.3347 (3)	0.23190 (19)	0.0847 (13)
F10	0.9283 (2)	0.1378 (3)	0.20278 (18)	0.0818 (13)
F11	1.0269 (2)	0.1392 (3)	0.19496 (18)	0.0763 (11)
F12	1.0000	0.2364 (3)	0.2500	0.0754 (15)
F13	1.0000	0.0398 (4)	0.2500	0.0804 (16)
N1	0.9201 (2)	−0.0713 (3)	0.44496 (19)	0.0448 (9)
N2	0.87153 (19)	0.0374 (3)	0.49961 (18)	0.0432 (9)
N3	0.70185 (19)	0.3064 (3)	0.03589 (19)	0.0426 (9)
N4	0.6112 (2)	0.1930 (3)	0.0059 (2)	0.0543 (11)
N5	0.8656 (2)	0.4525 (3)	0.1661 (2)	0.0563 (12)
O1	0.8409 (2)	−0.0135 (2)	0.32697 (17)	0.0540 (9)
O2	0.78393 (19)	0.0986 (3)	0.38742 (16)	0.0525 (9)
O3	0.7459 (2)	0.2565 (3)	0.16091 (18)	0.0587 (10)
O4	0.6461 (2)	0.1362 (3)	0.12907 (17)	0.0579 (10)
P1	0.84452 (8)	0.37264 (11)	0.45477 (8)	0.0624 (4)
P2	0.5000	0.26347 (15)	0.2500	0.0622 (6)
P3	1.0000	0.13821 (16)	0.2500	0.0657 (6)
Pd1	0.850980 (18)	0.01366 (2)	0.411300 (16)	0.04146 (12)
Pd2	0.67660 (2)	0.22273 (2)	0.086740 (17)	0.04501 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.061 (3)	0.048 (3)	0.062 (3)	0.005 (2)	0.031 (3)	0.008 (2)
C2	0.068 (3)	0.042 (2)	0.065 (3)	0.002 (2)	0.048 (3)	0.005 (2)
C3	0.052 (3)	0.054 (3)	0.062 (3)	0.011 (2)	0.033 (3)	0.021 (2)
C4	0.048 (3)	0.049 (3)	0.060 (3)	−0.002 (2)	0.012 (2)	0.019 (2)
C5	0.036 (2)	0.045 (3)	0.061 (3)	−0.0044 (19)	0.015 (2)	0.017 (2)
C6	0.045 (3)	0.048 (3)	0.045 (3)	−0.008 (2)	0.013 (2)	0.016 (2)
C7	0.051 (3)	0.057 (3)	0.046 (3)	−0.009 (2)	0.010 (2)	0.018 (2)
C8	0.065 (3)	0.065 (4)	0.037 (3)	−0.016 (3)	0.017 (2)	−0.004 (2)
C9	0.069 (4)	0.065 (4)	0.047 (3)	−0.003 (3)	0.024 (3)	−0.009 (3)
C10	0.042 (3)	0.068 (3)	0.046 (3)	0.005 (2)	0.017 (2)	0.004 (2)
C11	0.061 (3)	0.063 (4)	0.048 (3)	0.013 (3)	0.031 (3)	0.001 (3)
C12	0.067 (3)	0.057 (3)	0.042 (3)	0.003 (3)	0.020 (2)	0.007 (2)
C13	0.058 (3)	0.068 (4)	0.038 (3)	0.007 (3)	0.015 (2)	0.008 (2)
C14	0.053 (3)	0.066 (4)	0.042 (3)	0.013 (3)	0.008 (2)	0.003 (2)
C15	0.067 (4)	0.066 (4)	0.061 (4)	0.032 (3)	0.021 (3)	0.018 (3)
C16	0.063 (4)	0.058 (3)	0.060 (4)	−0.012 (3)	0.008 (3)	0.013 (3)
C17	0.072 (4)	0.055 (3)	0.047 (3)	0.013 (3)	0.017 (3)	0.001 (2)
C18	0.055 (3)	0.066 (3)	0.040 (3)	0.003 (3)	0.013 (2)	0.013 (2)
C19	0.064 (3)	0.060 (3)	0.041 (3)	0.006 (3)	0.016 (3)	0.010 (2)
C20	0.066 (4)	0.066 (4)	0.061 (4)	−0.018 (3)	0.011 (3)	0.028 (3)
C21	0.060 (3)	0.059 (3)	0.054 (3)	0.015 (3)	0.018 (3)	0.009 (3)
C22	0.071 (4)	0.063 (4)	0.068 (4)	0.016 (3)	0.032 (3)	0.015 (3)
C23	0.074 (4)	0.076 (4)	0.059 (4)	0.003 (3)	0.018 (3)	0.016 (3)
C24	0.063 (3)	0.050 (3)	0.042 (3)	0.022 (2)	0.032 (2)	−0.002 (2)
C25	0.056 (3)	0.056 (3)	0.045 (3)	0.026 (3)	0.019 (2)	0.016 (2)
C26	0.056 (3)	0.057 (3)	0.046 (3)	0.025 (3)	0.019 (2)	0.013 (2)
C27	0.065 (4)	0.068 (4)	0.045 (3)	0.021 (3)	0.015 (3)	0.008 (3)
C28	0.058 (4)	0.069 (4)	0.056 (3)	0.021 (3)	0.003 (3)	−0.004 (3)
C29	0.061 (4)	0.061 (4)	0.069 (4)	0.008 (3)	0.006 (3)	−0.012 (3)
C30	0.064 (3)	0.061 (3)	0.055 (3)	0.014 (3)	0.028 (3)	0.007 (3)
C31	0.063 (4)	0.068 (4)	0.065 (4)	−0.002 (3)	0.016 (3)	−0.013 (3)
C32	0.064 (4)	0.061 (4)	0.079 (4)	−0.019 (3)	0.016 (3)	−0.014 (3)
F1	0.074 (3)	0.091 (3)	0.092 (3)	0.029 (2)	0.022 (2)	0.029 (2)
F2	0.086 (3)	0.092 (3)	0.077 (3)	0.017 (2)	−0.013 (2)	−0.027 (2)
F3	0.079 (3)	0.110 (3)	0.075 (3)	0.036 (2)	0.038 (2)	0.013 (2)
F4	0.086 (3)	0.083 (3)	0.079 (3)	0.010 (2)	0.036 (2)	−0.019 (2)
F5	0.086 (3)	0.081 (3)	0.090 (3)	−0.025 (2)	0.030 (2)	−0.020 (2)
F6	0.086 (3)	0.083 (3)	0.083 (3)	−0.011 (2)	0.015 (2)	0.011 (2)
F7	0.088 (3)	0.087 (3)	0.085 (3)	0.000 (2)	−0.026 (3)	−0.006 (2)
F8	0.092 (3)	0.094 (3)	0.080 (3)	0.014 (2)	0.016 (2)	−0.044 (2)
F9	0.079 (3)	0.107 (3)	0.071 (2)	−0.040 (2)	0.029 (2)	−0.006 (2)
F10	0.078 (3)	0.086 (3)	0.054 (2)	−0.006 (2)	−0.0137 (19)	0.0170 (18)
F11	0.087 (3)	0.072 (2)	0.061 (2)	−0.021 (2)	0.013 (2)	−0.0162 (18)
F12	0.086 (4)	0.062 (3)	0.065 (3)	0.000	0.009 (3)	0.000
F13	0.082 (4)	0.062 (3)	0.077 (4)	0.000	0.001 (3)	0.000
N1	0.048 (2)	0.039 (2)	0.050 (2)	0.0022 (16)	0.0192 (19)	0.0081 (17)
N2	0.039 (2)	0.050 (2)	0.040 (2)	−0.0046 (17)	0.0118 (17)	0.0048 (17)
N3	0.0367 (18)	0.049 (2)	0.047 (2)	0.0225 (17)	0.0195 (17)	0.0130 (17)
N4	0.059 (3)	0.056 (3)	0.049 (3)	0.018 (2)	0.019 (2)	0.011 (2)
N5	0.064 (3)	0.050 (3)	0.056 (3)	−0.025 (2)	0.022 (2)	−0.017 (2)
O1	0.065 (2)	0.060 (2)	0.0407 (19)	0.0162 (18)	0.0213 (17)	0.0045 (16)
O2	0.063 (2)	0.058 (2)	0.0373 (18)	0.0182 (18)	0.0173 (16)	0.0063 (16)
O3	0.061 (2)	0.060 (2)	0.050 (2)	0.0003 (19)	0.0115 (18)	0.0078 (18)
O4	0.065 (2)	0.058 (2)	0.0405 (19)	−0.0097 (18)	0.0044 (17)	0.0174 (16)
P1	0.0580 (9)	0.0605 (9)	0.0717 (10)	0.0202 (7)	0.0256 (8)	−0.0011 (8)
P2	0.0601 (13)	0.0558 (12)	0.0631 (14)	0.000	0.0108 (11)	0.000
P3	0.0595 (13)	0.0639 (14)	0.0578 (13)	0.000	−0.0012 (10)	0.000
Pd1	0.0436 (2)	0.0467 (2)	0.0348 (2)	0.00376 (15)	0.01409 (15)	0.00597 (14)
Pd2	0.0549 (2)	0.0403 (2)	0.0389 (2)	0.01581 (16)	0.01452 (16)	0.01143 (15)

Geometric parameters (Å, º) top

C1—N1	1.343 (7)	C22—C23	1.359 (9)
C1—C2	1.380 (8)	C22—H22	0.9300
C1—H1	0.9300	C23—C24	1.368 (9)
C2—C3	1.368 (8)	C23—H23	0.9300
C2—H2	0.9300	C24—C25	1.372 (8)
C3—C4	1.374 (8)	C24—H24	0.9300
C3—H3	0.9300	C25—N3	1.380 (7)
C4—C5	1.377 (7)	C25—C26	1.438 (9)
C4—H4	0.9300	C26—N4	1.360 (7)
C5—N1	1.354 (7)	C26—C27	1.395 (8)
C5—C6	1.473 (8)	C27—C28	1.361 (10)
C6—N2	1.366 (7)	C27—H27	0.9300
C6—C7	1.381 (8)	C28—C29	1.406 (10)
C7—C8	1.359 (9)	C28—H28	0.9300
C7—H7	0.9300	C29—C30	1.374 (9)
C8—C9	1.374 (9)	C29—H29	0.9300
C8—H8	0.9300	C30—N4	1.295 (8)
C9—C10	1.392 (8)	C30—H30	0.9300
C9—H9	0.9300	C31—N5	1.122 (8)
C10—N2	1.325 (7)	C31—C32	1.398 (10)
C10—H10	0.9300	C32—H32A	0.9600
C11—C12	1.503 (7)	C32—H32B	0.9600
C11—H11A	0.9600	C32—H32C	0.9600
C11—H11B	0.9600	F1—P1	1.550 (4)
C11—H11C	0.9600	F2—P1	1.529 (4)
C12—O1	1.285 (7)	F3—P1	1.570 (4)
C12—C13	1.411 (9)	F4—P1	1.520 (4)
C13—C14	1.404 (8)	F5—P1	1.485 (5)
C13—C18	1.504 (7)	F6—P1	1.534 (5)
C14—O2	1.284 (7)	F7—P2	1.582 (4)
C14—C15	1.505 (8)	F8—P2	1.573 (4)
C15—H15A	0.9600	F9—P2	1.557 (4)
C15—H15B	0.9600	F10—P3	1.598 (4)
C15—H15C	0.9600	F11—P3	1.593 (4)
C16—C17	1.530 (8)	F12—P3	1.582 (6)
C16—H16A	0.9600	F13—P3	1.585 (6)
C16—H16B	0.9600	N1—Pd1	2.003 (4)
C16—H16C	0.9600	N2—Pd1	2.004 (4)
C17—O3	1.287 (7)	N3—Pd2	2.000 (4)
C17—C18	1.377 (9)	N4—Pd2	2.017 (5)
C18—C19	1.405 (8)	O1—Pd1	1.966 (4)
C19—O4	1.294 (6)	O2—Pd1	1.953 (4)
C19—C20	1.495 (8)	O3—Pd2	1.968 (4)
C20—H20A	0.9600	O4—Pd2	1.958 (4)
C20—H20B	0.9600	P2—F9ⁱ	1.557 (4)
C20—H20C	0.9600	P2—F8ⁱ	1.573 (4)
C21—N3	1.335 (8)	P2—F7ⁱ	1.582 (4)
C21—C22	1.350 (9)	P3—F11ⁱⁱ	1.593 (4)
C21—H21	0.9300	P3—F10ⁱⁱ	1.598 (4)

N1—C1—C2	121.0 (6)	C28—C27—H27	120.4
N1—C1—H1	119.5	C26—C27—H27	120.4
C2—C1—H1	119.5	C27—C28—C29	120.5 (6)
C3—C2—C1	119.4 (5)	C27—C28—H28	119.8
C3—C2—H2	120.3	C29—C28—H28	119.8
C1—C2—H2	120.3	C30—C29—C28	116.5 (7)
C2—C3—C4	119.4 (5)	C30—C29—H29	121.7
C2—C3—H3	120.3	C28—C29—H29	121.7
C4—C3—H3	120.3	N4—C30—C29	123.5 (6)
C3—C4—C5	119.7 (6)	N4—C30—H30	118.3
C3—C4—H4	120.1	C29—C30—H30	118.3
C5—C4—H4	120.1	N5—C31—C32	174.8 (8)
N1—C5—C4	120.5 (6)	C31—C32—H32A	109.5
N1—C5—C6	114.9 (4)	C31—C32—H32B	109.5
C4—C5—C6	124.6 (5)	H32A—C32—H32B	109.5
N2—C6—C7	120.2 (5)	C31—C32—H32C	109.5
N2—C6—C5	114.3 (5)	H32A—C32—H32C	109.5
C7—C6—C5	125.5 (5)	H32B—C32—H32C	109.5
C8—C7—C6	119.7 (5)	C1—N1—C5	119.8 (5)
C8—C7—H7	120.1	C1—N1—Pd1	125.2 (4)
C6—C7—H7	120.1	C5—N1—Pd1	114.9 (4)
C7—C8—C9	120.1 (5)	C10—N2—C6	120.0 (5)
C7—C8—H8	120.0	C10—N2—Pd1	125.3 (4)
C9—C8—H8	120.0	C6—N2—Pd1	114.7 (4)
C8—C9—C10	118.7 (6)	C21—N3—C25	120.0 (5)
C8—C9—H9	120.7	C21—N3—Pd2	126.0 (4)
C10—C9—H9	120.7	C25—N3—Pd2	114.0 (4)
N2—C10—C9	121.3 (5)	C30—N4—C26	121.1 (5)
N2—C10—H10	119.3	C30—N4—Pd2	126.0 (4)
C9—C10—H10	119.3	C26—N4—Pd2	112.9 (4)
C12—C11—H11A	109.5	C12—O1—Pd1	124.6 (4)
C12—C11—H11B	109.5	C14—O2—Pd1	125.3 (4)
H11A—C11—H11B	109.5	C17—O3—Pd2	123.7 (4)
C12—C11—H11C	109.5	C19—O4—Pd2	124.3 (4)
H11A—C11—H11C	109.5	F5—P1—F4	96.5 (3)
H11B—C11—H11C	109.5	F5—P1—F2	90.4 (3)
O1—C12—C13	126.5 (5)	F4—P1—F2	88.9 (3)
O1—C12—C11	111.8 (5)	F5—P1—F6	174.6 (3)
C13—C12—C11	121.7 (5)	F4—P1—F6	88.5 (3)
C14—C13—C12	123.2 (5)	F2—P1—F6	91.6 (3)
C14—C13—C18	118.9 (5)	F5—P1—F1	87.8 (3)
C12—C13—C18	117.9 (5)	F4—P1—F1	90.6 (3)
O2—C14—C13	126.5 (5)	F2—P1—F1	178.1 (3)
O2—C14—C15	112.5 (5)	F6—P1—F1	90.3 (3)
C13—C14—C15	120.9 (5)	F5—P1—F3	87.0 (3)
C14—C15—H15A	109.5	F4—P1—F3	176.5 (3)
C14—C15—H15B	109.5	F2—P1—F3	90.8 (3)
H15A—C15—H15B	109.5	F6—P1—F3	88.0 (3)
C14—C15—H15C	109.5	F1—P1—F3	89.7 (2)
H15A—C15—H15C	109.5	F9—P2—F9ⁱ	85.2 (4)
H15B—C15—H15C	109.5	F9—P2—F8ⁱ	177.7 (2)
C17—C16—H16A	109.5	F9ⁱ—P2—F8ⁱ	94.1 (3)
C17—C16—H16B	109.5	F9—P2—F8	94.1 (3)
H16A—C16—H16B	109.5	F9ⁱ—P2—F8	177.7 (2)
C17—C16—H16C	109.5	F8ⁱ—P2—F8	86.6 (4)
H16A—C16—H16C	109.5	F9—P2—F7ⁱ	89.2 (3)
H16B—C16—H16C	109.5	F9ⁱ—P2—F7ⁱ	91.4 (3)
O3—C17—C18	127.8 (6)	F8ⁱ—P2—F7ⁱ	88.6 (3)
O3—C17—C16	110.5 (6)	F8—P2—F7ⁱ	90.7 (3)
C18—C17—C16	121.7 (5)	F9—P2—F7	91.4 (3)
C17—C18—C19	123.1 (5)	F9ⁱ—P2—F7	89.2 (3)
C17—C18—C13	119.2 (5)	F8ⁱ—P2—F7	90.7 (3)
C19—C18—C13	117.7 (5)	F8—P2—F7	88.6 (3)
O4—C19—C18	126.4 (5)	F7ⁱ—P2—F7	179.1 (4)
O4—C19—C20	112.0 (5)	F12—P3—F13	180.000 (1)
C18—C19—C20	121.6 (5)	F12—P3—F11ⁱⁱ	89.40 (17)
C19—C20—H20A	109.5	F13—P3—F11ⁱⁱ	90.60 (17)
C19—C20—H20B	109.5	F12—P3—F11	89.40 (17)
H20A—C20—H20B	109.5	F13—P3—F11	90.60 (17)
C19—C20—H20C	109.5	F11ⁱⁱ—P3—F11	178.8 (3)
H20A—C20—H20C	109.5	F12—P3—F10	90.21 (18)
H20B—C20—H20C	109.5	F13—P3—F10	89.79 (18)
N3—C21—C22	121.6 (6)	F11ⁱⁱ—P3—F10	90.6 (2)
N3—C21—H21	119.2	F11—P3—F10	89.4 (2)
C22—C21—H21	119.2	F12—P3—F10ⁱⁱ	90.21 (18)
C21—C22—C23	120.1 (7)	F13—P3—F10ⁱⁱ	89.79 (18)
C21—C22—H22	119.9	F11ⁱⁱ—P3—F10ⁱⁱ	89.4 (2)
C23—C22—H22	119.9	F11—P3—F10ⁱⁱ	90.6 (2)
C22—C23—C24	119.0 (6)	F10—P3—F10ⁱⁱ	179.6 (4)
C22—C23—H23	120.5	N1—Pd1—N2	81.12 (18)
C24—C23—H23	120.5	N1—Pd1—O1	93.32 (17)
C23—C24—C25	121.0 (6)	N1—Pd1—O2	173.83 (16)
C23—C24—H24	119.5	N2—Pd1—O1	173.59 (17)
C25—C24—H24	119.5	N2—Pd1—O2	92.78 (16)
C24—C25—N3	118.3 (6)	N3—Pd2—O3	92.97 (18)
C24—C25—C26	127.2 (5)	N3—Pd2—O4	174.35 (18)
N3—C25—C26	114.4 (5)	N3—Pd2—N4	81.59 (19)
N4—C26—C27	119.2 (6)	N4—Pd2—O3	174.05 (19)
N4—C26—C25	116.9 (5)	N4—Pd2—O4	92.80 (18)
C27—C26—C25	123.9 (5)	O1—Pd1—O2	92.82 (15)
C28—C27—C26	119.2 (6)	O3—Pd2—O4	92.62 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F2ⁱⁱⁱ	0.93	2.45	3.200 (8)	138
C7—H7···F11^iv	0.93	2.45	3.332 (7)	157
C21—H21···N5	0.93	2.57	3.310 (8)	137
C22—H22···F3^v	0.93	2.47	3.209 (8)	136
C24—H24···F10^vi	0.93	2.47	3.357 (6)	160
C27—H27···F10^vi	0.93	2.39	3.282 (8)	160

Symmetry codes: (iii) −x+2, −y, −z+1; (iv) x, −y, z+1/2; (v) x, −y+1, z−1/2; (vi) −x+3/2, −y+1/2, −z.

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