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A range of single-crystal structures of the type [Pd(cod)(LL′-Bid)]A, where LL′-Bid = acetylacetonato (acac), thenoyltrifluoroactetonato (thtfac) and hexafluoroacetylacetonato (hfacac), and A = tetrafluoroborate (BF4) and hexafluoro­phosphate (PF6), are reported. The complexes [Pd(cod)(acac)]PF6 (I), [Pd(cod)(thtfac)]PF6 (III), [Pd(cod)(thtfac)]BF4 (IV) and [Pd(cod)(hfacac)]PF6 (V) are isostructural in the monoclinic space group P21/c. The influence of the variation of the β-diketonato-type ligands on the coordination geometry of cis,cis-1,5-cycloocta-1,5-diene (cod) was investigated and found that no significant changes to the Pd—C and C=C bond distances were observed. The `Venus fly trap' parameters vary by 7.8° for the `jaw' angle (ψ), while the `bite' angle (χ) remains virtually constant.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519212046738/eb5019sup1.cif
Contains datablocks 8Fth3, 10rth5_0ma, 9Tth12_L, 10Rth7, 10ath3_0m, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212046738/eb50198Fth3sup2.hkl
Contains datablock new

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212046738/eb501910rth5_0masup3.hkl
Contains datablock 10rth5_0ma

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212046738/eb50199Tth12_Lsup4.hkl
Contains datablock new

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212046738/eb501910Rth7sup5.hkl
Contains datablock new

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212046738/eb501910ath3_0msup6.hkl
Contains datablock 10ath3_0m

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052519212046738/eb5019sup7.pdf
Hydrogen-bond tables and molecular diagrams

Computing details top

Data collection: Bruker APEX2 (Bruker, 2005) for 8Fth3, 10rth5_0ma, 10Rth7, 10ath3_0m; CrysAlis CCD (Oxford Diffraction, 2006) for 9Tth12_L. Cell refinement: Bruker SAINT-Plus (Bruker, 2004) for 8Fth3, 10rth5_0ma, 10Rth7, 10ath3_0m; CrysAlis RED (Oxford Diffraction, 2006) for 9Tth12_L. Data reduction: Bruker SAINT-Plus and XPREP (Bruker, 2004) for 8Fth3, 10rth5_0ma, 10Rth7, 10ath3_0m; CrysAlis RED (Oxford Diffraction, 2006) for 9Tth12_L. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: DIAMOND 3.0c (Brandenburg & Putz, 2005) for 8Fth3, 10rth5_0ma, 10Rth7, 10ath3_0m; DIAMOND 3.0c (Brandenburg & Putz, 2004) for 9Tth12_L. For all compounds, software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
(8Fth3) (acetylacetonato)(η4-cyclo-octa-1,5-dienyl)palladium(II) hexafluorophosphate top
Crystal data top
C13H19O2Pd·F6PF(000) = 912
Mr = 458.65Dx = 1.917 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4688 reflections
a = 9.3166 (6) Åθ = 3.2–28.3°
b = 15.4676 (8) ŵ = 1.34 mm1
c = 12.6132 (6) ÅT = 100 K
β = 119.016 (4)°Cuboid, colourless
V = 1589.49 (15) Å30.13 × 0.07 × 0.03 mm
Z = 4
Data collection top
Bruker X8 Apex II 4K Kappa CCD
diffractometer
3952 independent reflections
Radiation source: sealed tube3112 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 512 pixels mm-1θmax = 28.3°, θmin = 3.3°
ϕ and ω scansh = 1212
Absorption correction: multi-scan
SADABS (Bruker, 2004)
k = 1320
Tmin = 0.846, Tmax = 0.961l = 1616
10747 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0345P)2 + 0.1476P]
where P = (Fo2 + 2Fc2)/3
3952 reflections(Δ/σ)max = 0.001
210 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.67 e Å3
Crystal data top
C13H19O2Pd·F6PV = 1589.49 (15) Å3
Mr = 458.65Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.3166 (6) ŵ = 1.34 mm1
b = 15.4676 (8) ÅT = 100 K
c = 12.6132 (6) Å0.13 × 0.07 × 0.03 mm
β = 119.016 (4)°
Data collection top
Bruker X8 Apex II 4K Kappa CCD
diffractometer
3952 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2004)
3112 reflections with I > 2σ(I)
Tmin = 0.846, Tmax = 0.961Rint = 0.041
10747 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.081H-atom parameters constrained
S = 1.05Δρmax = 0.70 e Å3
3952 reflectionsΔρmin = 0.67 e Å3
210 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.1389 (4)0.08218 (19)0.1348 (3)0.0179 (7)
H11.13530.02370.09990.021*
C21.0027 (4)0.1320 (2)0.0658 (3)0.0182 (7)
H20.91920.10320.01030.022*
C30.9930 (4)0.22943 (19)0.0621 (3)0.0198 (7)
H3A0.8770.24690.02990.024*
H3B1.02980.2510.00520.024*
C41.0966 (4)0.27235 (19)0.1856 (3)0.0184 (7)
H4A1.21140.27710.20180.022*
H4B1.05490.33160.18330.022*
C51.0935 (4)0.22237 (17)0.2879 (3)0.0147 (6)
H51.04310.25470.33030.018*
C61.2094 (4)0.16217 (18)0.3596 (3)0.0152 (6)
H61.2280.1590.44450.018*
C71.3519 (4)0.1317 (2)0.3455 (3)0.0197 (7)
H7A1.39360.0770.39110.024*
H7B1.4410.1750.38240.024*
C81.3114 (4)0.1167 (2)0.2134 (3)0.0202 (7)
H8A1.32360.17190.17890.024*
H8B1.39130.07510.2120.024*
C90.7323 (4)0.03520 (18)0.1496 (3)0.0173 (7)
C100.7097 (4)0.01654 (18)0.2488 (3)0.0165 (6)
H100.62280.0460.25260.02*
C110.8017 (4)0.04091 (17)0.3429 (3)0.0129 (6)
C120.6246 (4)0.10134 (19)0.0580 (3)0.0224 (7)
H12A0.55790.07320.02050.034*
H12B0.55250.1280.08510.034*
H12C0.69330.1460.04990.034*
C130.7626 (4)0.0515 (2)0.4446 (3)0.0190 (7)
H13A0.86110.03970.52210.029*
H13B0.67570.01080.43350.029*
H13C0.72550.11070.44470.029*
O10.8401 (3)0.00150 (12)0.12611 (18)0.0169 (5)
O20.9223 (3)0.08719 (12)0.35432 (18)0.0149 (4)
F10.5466 (3)0.19410 (13)0.35376 (18)0.0373 (5)
F20.3063 (3)0.25654 (13)0.2171 (2)0.0436 (6)
F30.1666 (3)0.14130 (13)0.22856 (19)0.0379 (5)
F40.4062 (3)0.08044 (11)0.3662 (2)0.0370 (6)
F50.3406 (3)0.21443 (13)0.39866 (17)0.0358 (5)
F60.3687 (3)0.12125 (15)0.18342 (18)0.0410 (6)
P10.35617 (11)0.16884 (5)0.29156 (7)0.01942 (19)
Pd10.99194 (3)0.092702 (13)0.22746 (2)0.01228 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0245 (19)0.0195 (15)0.0172 (16)0.0005 (13)0.0161 (14)0.0043 (12)
C20.0247 (19)0.0226 (16)0.0128 (15)0.0029 (14)0.0133 (14)0.0019 (12)
C30.0250 (19)0.0215 (16)0.0144 (15)0.0020 (14)0.0108 (14)0.0020 (12)
C40.0215 (18)0.0142 (14)0.0232 (16)0.0021 (13)0.0137 (15)0.0009 (12)
C50.0202 (18)0.0109 (13)0.0130 (14)0.0049 (12)0.0082 (13)0.0044 (11)
C60.0161 (17)0.0171 (15)0.0122 (14)0.0035 (12)0.0068 (13)0.0046 (11)
C70.0128 (17)0.0230 (16)0.0205 (16)0.0004 (13)0.0061 (14)0.0012 (13)
C80.0166 (17)0.0207 (15)0.0275 (18)0.0004 (13)0.0140 (15)0.0043 (13)
C90.0147 (17)0.0110 (14)0.0216 (16)0.0043 (12)0.0053 (14)0.0025 (12)
C100.0132 (16)0.0145 (14)0.0228 (16)0.0016 (12)0.0095 (13)0.0037 (12)
C110.0123 (16)0.0103 (13)0.0163 (15)0.0048 (11)0.0070 (13)0.0046 (11)
C120.0245 (19)0.0189 (16)0.0240 (18)0.0016 (14)0.0120 (15)0.0031 (12)
C130.0142 (17)0.0219 (16)0.0230 (17)0.0011 (13)0.0107 (14)0.0012 (13)
O10.0154 (12)0.0173 (10)0.0186 (11)0.0052 (9)0.0087 (9)0.0051 (8)
O20.0122 (11)0.0185 (10)0.0145 (11)0.0012 (9)0.0070 (9)0.0011 (8)
F10.0207 (12)0.0448 (13)0.0398 (13)0.0027 (10)0.0096 (10)0.0068 (10)
F20.0447 (16)0.0365 (12)0.0398 (13)0.0138 (11)0.0128 (12)0.0234 (10)
F30.0200 (12)0.0431 (12)0.0484 (14)0.0005 (10)0.0149 (11)0.0140 (10)
F40.0471 (16)0.0232 (10)0.0390 (13)0.0086 (10)0.0195 (12)0.0098 (9)
F50.0434 (15)0.0392 (12)0.0261 (11)0.0107 (10)0.0180 (10)0.0073 (9)
F60.0289 (13)0.0697 (15)0.0229 (11)0.0187 (12)0.0114 (10)0.0064 (10)
P10.0177 (5)0.0216 (4)0.0181 (4)0.0064 (3)0.0079 (4)0.0034 (3)
Pd10.01225 (13)0.01267 (12)0.01238 (13)0.00086 (9)0.00634 (10)0.00065 (8)
Geometric parameters (Å, º) top
C1—C21.375 (5)C8—H8B0.99
C1—C81.518 (5)C9—O11.286 (4)
C1—Pd12.196 (3)C9—C101.397 (4)
C1—H11C9—C121.504 (4)
C2—C31.509 (4)C10—C111.395 (4)
C2—Pd12.176 (3)C10—H100.95
C2—H21C11—O21.280 (3)
C3—C41.530 (4)C11—C131.503 (4)
C3—H3A0.99C12—H12A0.98
C3—H3B0.99C12—H12B0.98
C4—C51.516 (4)C12—H12C0.98
C4—H4A0.99C13—H13A0.98
C4—H4B0.99C13—H13B0.98
C5—C61.380 (4)C13—H13C0.98
C5—Pd12.191 (3)O1—Pd12.0012 (19)
C5—H51O2—Pd11.999 (2)
C6—C71.498 (4)F1—P11.602 (2)
C6—Pd12.182 (3)F2—P11.586 (2)
C6—H61F3—P11.604 (2)
C7—C81.537 (4)F4—P11.5962 (19)
C7—H7A0.99F5—P11.591 (2)
C7—H7B0.99F6—P11.603 (2)
C8—H8A0.99
C2—C1—C8125.2 (3)C11—C10—C9126.6 (3)
C2—C1—Pd170.90 (18)C11—C10—H10116.7
C8—C1—Pd1111.2 (2)C9—C10—H10116.7
C2—C1—H1113.9O2—C11—C10126.5 (3)
C8—C1—H1113.9O2—C11—C13114.0 (3)
Pd1—C1—H1113.9C10—C11—C13119.5 (3)
C1—C2—C3127.0 (3)C9—C12—H12A109.5
C1—C2—Pd172.44 (18)C9—C12—H12B109.5
C3—C2—Pd1106.18 (19)H12A—C12—H12B109.5
C1—C2—H2114.1C9—C12—H12C109.5
C3—C2—H2114.1H12A—C12—H12C109.5
Pd1—C2—H2114.1H12B—C12—H12C109.5
C2—C3—C4113.8 (3)C11—C13—H13A109.5
C2—C3—H3A108.8C11—C13—H13B109.5
C4—C3—H3A108.8H13A—C13—H13B109.5
C2—C3—H3B108.8C11—C13—H13C109.5
C4—C3—H3B108.8H13A—C13—H13C109.5
H3A—C3—H3B107.7H13B—C13—H13C109.5
C5—C4—C3112.5 (2)C9—O1—Pd1122.48 (19)
C5—C4—H4A109.1C11—O2—Pd1122.82 (18)
C3—C4—H4A109.1F2—P1—F590.13 (12)
C5—C4—H4B109.1F2—P1—F4179.88 (17)
C3—C4—H4B109.1F5—P1—F489.97 (12)
H4A—C4—H4B107.8F2—P1—F191.05 (12)
C6—C5—C4124.7 (3)F5—P1—F190.65 (12)
C6—C5—Pd171.26 (16)F4—P1—F189.02 (12)
C4—C5—Pd1110.73 (18)F2—P1—F690.61 (13)
C6—C5—H5114.1F5—P1—F6178.64 (14)
C4—C5—H5114.1F4—P1—F689.30 (12)
Pd1—C5—H5114.1F1—P1—F690.47 (13)
C5—C6—C7126.3 (3)F2—P1—F389.87 (13)
C5—C6—Pd171.95 (17)F5—P1—F390.37 (12)
C7—C6—Pd1107.63 (19)F4—P1—F390.05 (12)
C5—C6—H6114.1F1—P1—F3178.62 (12)
C7—C6—H6114.1F6—P1—F388.49 (12)
Pd1—C6—H6114.1O2—Pd1—O194.41 (8)
C6—C7—C8114.2 (3)O2—Pd1—C2160.46 (10)
C6—C7—H7A108.7O1—Pd1—C286.82 (10)
C8—C7—H7A108.7O2—Pd1—C687.21 (10)
C6—C7—H7B108.7O1—Pd1—C6162.43 (10)
C8—C7—H7B108.7C2—Pd1—C697.49 (12)
H7A—C7—H7B107.6O2—Pd1—C590.78 (10)
C1—C8—C7112.8 (3)O1—Pd1—C5160.23 (10)
C1—C8—H8A109C2—Pd1—C582.06 (11)
C7—C8—H8A109C6—Pd1—C536.79 (11)
C1—C8—H8B109O2—Pd1—C1162.06 (10)
C7—C8—H8B109O1—Pd1—C192.08 (10)
H8A—C8—H8B107.8C2—Pd1—C136.66 (12)
O1—C9—C10126.6 (3)C6—Pd1—C181.67 (12)
O1—C9—C12113.8 (3)C5—Pd1—C188.71 (11)
C10—C9—C12119.6 (3)
C8—C1—C2—C35.7 (5)C3—C2—Pd1—O243.5 (4)
Pd1—C1—C2—C397.3 (3)C1—C2—Pd1—O197.80 (19)
C8—C1—C2—Pd1103.0 (3)C3—C2—Pd1—O1137.7 (2)
C1—C2—C3—C437.9 (4)C1—C2—Pd1—C665.08 (19)
Pd1—C2—C3—C442.1 (3)C3—C2—Pd1—C659.4 (2)
C2—C3—C4—C538.2 (4)C1—C2—Pd1—C598.6 (2)
C3—C4—C5—C694.8 (4)C3—C2—Pd1—C525.9 (2)
C3—C4—C5—Pd113.7 (3)C3—C2—Pd1—C1124.5 (3)
C4—C5—C6—C73.7 (5)C5—C6—Pd1—O295.04 (18)
Pd1—C5—C6—C799.0 (3)C7—C6—Pd1—O2141.6 (2)
C4—C5—C6—Pd1102.7 (3)C5—C6—Pd1—O1169.2 (3)
C5—C6—C7—C841.2 (4)C7—C6—Pd1—O145.8 (4)
Pd1—C6—C7—C839.0 (3)C5—C6—Pd1—C265.90 (19)
C2—C1—C8—C793.4 (4)C7—C6—Pd1—C257.4 (2)
Pd1—C1—C8—C712.3 (3)C7—C6—Pd1—C5123.3 (3)
C6—C7—C8—C135.0 (4)C5—C6—Pd1—C199.08 (19)
O1—C9—C10—C111.4 (5)C7—C6—Pd1—C124.3 (2)
C12—C9—C10—C11178.0 (3)C6—C5—Pd1—O284.29 (18)
C9—C10—C11—O20.6 (5)C4—C5—Pd1—O2154.7 (2)
C9—C10—C11—C13178.5 (3)C6—C5—Pd1—O1170.3 (2)
C10—C9—O1—Pd13.8 (4)C4—C5—Pd1—O149.4 (4)
C12—C9—O1—Pd1176.70 (19)C6—C5—Pd1—C2114.0 (2)
C10—C11—O2—Pd15.2 (4)C4—C5—Pd1—C27.0 (2)
C13—C11—O2—Pd1175.62 (18)C4—C5—Pd1—C6121.0 (3)
C11—O2—Pd1—O17.6 (2)C6—C5—Pd1—C177.77 (19)
C11—O2—Pd1—C285.3 (4)C4—C5—Pd1—C143.2 (2)
C11—O2—Pd1—C6170.0 (2)C2—C1—Pd1—O2166.9 (3)
C11—O2—Pd1—C5153.3 (2)C8—C1—Pd1—O245.6 (4)
C11—O2—Pd1—C1118.4 (3)C2—C1—Pd1—O181.84 (19)
C9—O1—Pd1—O26.9 (2)C8—C1—Pd1—O1156.8 (2)
C9—O1—Pd1—C2153.6 (2)C8—C1—Pd1—C2121.3 (3)
C9—O1—Pd1—C6101.6 (4)C2—C1—Pd1—C6114.66 (19)
C9—O1—Pd1—C597.9 (3)C8—C1—Pd1—C66.6 (2)
C9—O1—Pd1—C1170.1 (2)C2—C1—Pd1—C578.40 (19)
C1—C2—Pd1—O2168.0 (2)C8—C1—Pd1—C542.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F60.952.393.295 (4)159
C7—H7A···F4i0.992.473.311 (4)143
C2—H2···F6ii12.523.366 (4)142
C2—H2···F3ii12.543.257 (4)129
C5—H5···F3iii12.363.142 (4)135
C8—H8A···F1iv0.992.533.481 (4)161
C6—H6···F1v12.453.242 (3)136
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z; (iii) x+1, y+1/2, z+1/2; (iv) x+2, y+1/2, z+1/2; (v) x+2, y, z+1.
(10rth5_0ma) (acetylacetonato)(η4-cyclo-octa-1,5-dienyl)palladium(II) tetrafluoroborate top
Crystal data top
C13H19O2Pd·BF4F(000) = 800
Mr = 400.49Dx = 1.815 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 8277 reflections
a = 26.2908 (11) Åθ = 2.8–28.4°
b = 7.1684 (3) ŵ = 1.31 mm1
c = 7.7782 (3) ÅT = 100 K
V = 1465.90 (10) Å3Needle, yellow
Z = 40.34 × 0.1 × 0.07 mm
Data collection top
Bruker X8 APEX-II 4K Kappa CCD
diffractometer
3117 independent reflections
Radiation source: sealed tube2960 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 512 pixels mm-1θmax = 28.4°, θmin = 3.0°
ϕ and ω scansh = 3535
Absorption correction: multi-scan
SADABS (Bruker, 2004)
k = 99
Tmin = 0.664, Tmax = 0.914l = 106
15654 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.062 w = 1/[σ2(Fo2) + (0.046P)2 + 0.7363P]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.005
3117 reflectionsΔρmax = 1.05 e Å3
192 parametersΔρmin = 0.61 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881, 1143 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (3)
Crystal data top
C13H19O2Pd·BF4V = 1465.90 (10) Å3
Mr = 400.49Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 26.2908 (11) ŵ = 1.31 mm1
b = 7.1684 (3) ÅT = 100 K
c = 7.7782 (3) Å0.34 × 0.1 × 0.07 mm
Data collection top
Bruker X8 APEX-II 4K Kappa CCD
diffractometer
3117 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2004)
2960 reflections with I > 2σ(I)
Tmin = 0.664, Tmax = 0.914Rint = 0.025
15654 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.062Δρmax = 1.05 e Å3
S = 0.93Δρmin = 0.61 e Å3
3117 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881, 1143 Friedel pairs
192 parametersAbsolute structure parameter: 0.01 (3)
1 restraint
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.60809 (9)0.5373 (3)0.1035 (6)0.0196 (6)
H10.63350.4350.08680.024*
C20.60891 (10)0.6160 (4)0.2663 (4)0.0201 (6)
H20.63450.5590.34580.024*
C30.56498 (16)0.7094 (5)0.3562 (5)0.0236 (8)
H3A0.57850.78870.44980.028*
H3B0.54330.61220.40930.028*
C40.53191 (12)0.8302 (4)0.2372 (4)0.0234 (7)
H4A0.50670.74970.17850.028*
H4B0.5130.92210.30740.028*
C50.56289 (9)0.9322 (4)0.1042 (5)0.0201 (6)
H50.56141.07110.11450.024*
C60.57207 (10)0.8689 (5)0.0620 (4)0.0217 (6)
H60.57550.97060.14920.026*
C70.55728 (17)0.6837 (5)0.1361 (5)0.0262 (9)
H7A0.57930.65740.23650.031*
H7B0.52180.69160.17780.031*
C80.56142 (12)0.5199 (5)0.0089 (4)0.0262 (7)
H8A0.53070.51670.06460.031*
H8B0.5630.40120.07370.031*
C90.75094 (10)0.8105 (3)0.1099 (4)0.0137 (6)
C100.75462 (11)0.9832 (4)0.0294 (4)0.0157 (5)
H100.78791.02860.00710.019*
C110.71414 (10)1.0961 (4)0.0217 (4)0.0159 (5)
C120.79890 (10)0.7101 (4)0.1601 (4)0.0184 (6)
H12A0.79690.67320.28120.028*
H12B0.82810.79290.14350.028*
H12C0.80290.59870.08840.028*
C130.72542 (12)1.2841 (4)0.1019 (4)0.0199 (6)
H13A0.7021.3060.19780.03*
H13B0.76051.28560.14430.03*
H13C0.7211.38220.01550.03*
B010.39222 (13)0.7791 (5)0.0047 (5)0.0218 (7)
O10.70986 (7)0.7205 (3)0.1445 (3)0.0166 (4)
O20.66675 (7)1.0606 (3)0.0062 (3)0.0178 (4)
F010.43805 (8)0.7577 (3)0.0801 (4)0.0446 (5)
F020.38406 (12)0.6316 (3)0.1112 (4)0.0598 (8)
F030.35462 (9)0.7848 (5)0.1197 (5)0.0629 (10)
F040.39108 (7)0.9455 (2)0.0947 (4)0.0378 (4)
Pd10.640693 (6)0.81950 (2)0.08800 (5)0.01336 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0161 (11)0.0167 (10)0.0260 (18)0.0022 (8)0.0013 (14)0.0066 (15)
C20.0169 (13)0.0212 (13)0.0222 (15)0.0027 (11)0.0008 (11)0.0090 (12)
C30.0234 (19)0.0301 (17)0.0173 (17)0.0031 (14)0.0061 (14)0.0026 (13)
C40.0176 (14)0.0299 (16)0.0227 (16)0.0030 (11)0.0057 (12)0.0038 (12)
C50.0128 (10)0.0231 (12)0.0244 (16)0.0061 (9)0.0005 (14)0.0017 (15)
C60.0117 (12)0.0312 (15)0.0222 (15)0.0036 (11)0.0032 (11)0.0091 (13)
C70.0186 (17)0.042 (2)0.0176 (18)0.0042 (13)0.0015 (14)0.0009 (13)
C80.0214 (14)0.0308 (16)0.0265 (16)0.0070 (12)0.0027 (13)0.0040 (13)
C90.0146 (11)0.0155 (10)0.0109 (19)0.0001 (8)0.0001 (11)0.0012 (10)
C100.0141 (12)0.0152 (11)0.0178 (11)0.0028 (10)0.0012 (9)0.0007 (10)
C110.0203 (12)0.0144 (12)0.0130 (12)0.0026 (10)0.0002 (11)0.0010 (10)
C120.0123 (12)0.0181 (12)0.0249 (15)0.0012 (10)0.0014 (11)0.0045 (11)
C130.0223 (15)0.0124 (11)0.0249 (15)0.0006 (10)0.0041 (12)0.0048 (11)
B010.0210 (16)0.0197 (15)0.0246 (18)0.0001 (12)0.0007 (13)0.0032 (14)
O10.0120 (8)0.0151 (8)0.0226 (10)0.0001 (7)0.0009 (7)0.0043 (7)
O20.0172 (9)0.0156 (9)0.0207 (10)0.0009 (7)0.0005 (8)0.0044 (8)
F010.0289 (11)0.0441 (12)0.0606 (16)0.0020 (10)0.0140 (11)0.0057 (12)
F020.0979 (19)0.0327 (10)0.0488 (19)0.0024 (12)0.0334 (17)0.0115 (14)
F030.0341 (14)0.086 (2)0.069 (2)0.0305 (12)0.0226 (12)0.0440 (18)
F040.0533 (11)0.0263 (8)0.0338 (10)0.0028 (7)0.0022 (15)0.0121 (14)
Pd10.01080 (9)0.01499 (9)0.01429 (10)0.00024 (5)0.00009 (12)0.00345 (11)
Geometric parameters (Å, º) top
C1—C21.387 (6)C8—H8A0.99
C1—C81.511 (4)C8—H8B0.99
C1—Pd12.200 (2)C9—O11.287 (3)
C1—H11C9—C101.390 (3)
C2—C31.507 (5)C9—C121.504 (4)
C2—Pd12.180 (3)C10—C111.395 (4)
C2—H21C10—H100.95
C3—C41.537 (5)C11—O21.277 (3)
C3—H3A0.99C11—C131.514 (4)
C3—H3B0.99C12—H12A0.98
C4—C51.506 (5)C12—H12B0.98
C4—H4A0.99C12—H12C0.98
C4—H4B0.99C13—H13A0.98
C5—C61.391 (5)C13—H13B0.98
C5—Pd12.203 (2)C13—H13C0.98
C5—H51B01—F021.360 (5)
C6—C71.498 (5)B01—F011.382 (4)
C6—Pd12.177 (3)B01—F041.383 (4)
C6—H61B01—F031.384 (4)
C7—C81.540 (5)O1—Pd12.0011 (19)
C7—H7A0.99O2—Pd11.9980 (18)
C7—H7B0.99
C2—C1—C8125.0 (3)C7—C8—H8B109.3
C2—C1—Pd170.73 (15)H8A—C8—H8B108
C8—C1—Pd1111.1 (2)O1—C9—C10126.8 (2)
C2—C1—H1114O1—C9—C12114.1 (2)
C8—C1—H1114C10—C9—C12119.0 (2)
Pd1—C1—H1114C9—C10—C11126.3 (3)
C1—C2—C3126.3 (3)C9—C10—H10116.8
C1—C2—Pd172.36 (17)C11—C10—H10116.8
C3—C2—Pd1107.0 (2)O2—C11—C10127.0 (2)
C1—C2—H2114.2O2—C11—C13114.1 (2)
C3—C2—H2114.2C10—C11—C13119.0 (2)
Pd1—C2—H2114.2C9—C12—H12A109.5
C2—C3—C4113.9 (3)C9—C12—H12B109.5
C2—C3—H3A108.8H12A—C12—H12B109.5
C4—C3—H3A108.8C9—C12—H12C109.5
C2—C3—H3B108.8H12A—C12—H12C109.5
C4—C3—H3B108.8H12B—C12—H12C109.5
H3A—C3—H3B107.7C11—C13—H13A109.5
C5—C4—C3112.4 (3)C11—C13—H13B109.5
C5—C4—H4A109.1H13A—C13—H13B109.5
C3—C4—H4A109.1C11—C13—H13C109.5
C5—C4—H4B109.1H13A—C13—H13C109.5
C3—C4—H4B109.1H13B—C13—H13C109.5
H4A—C4—H4B107.9F02—B01—F01110.0 (3)
C6—C5—C4125.0 (3)F02—B01—F04111.1 (3)
C6—C5—Pd170.49 (15)F01—B01—F04110.8 (3)
C4—C5—Pd1111.30 (19)F02—B01—F03109.6 (3)
C6—C5—H5114F01—B01—F03107.0 (3)
C4—C5—H5114F04—B01—F03108.2 (3)
Pd1—C5—H5114C9—O1—Pd1122.60 (16)
C5—C6—C7127.0 (3)C11—O2—Pd1122.80 (17)
C5—C6—Pd172.48 (16)O2—Pd1—O194.35 (8)
C7—C6—Pd1106.1 (2)O2—Pd1—C686.97 (10)
C5—C6—H6114.1O1—Pd1—C6158.19 (11)
C7—C6—H6114.1O2—Pd1—C2160.69 (10)
Pd1—C6—H6114.1O1—Pd1—C288.35 (9)
C6—C7—C8114.2 (3)C6—Pd1—C297.58 (11)
C6—C7—H7A108.7O2—Pd1—C1161.58 (14)
C8—C7—H7A108.7O1—Pd1—C190.91 (9)
C6—C7—H7B108.7C6—Pd1—C181.72 (12)
C8—C7—H7B108.7C2—Pd1—C136.91 (15)
H7A—C7—H7B107.6O2—Pd1—C591.27 (9)
C1—C8—C7111.5 (3)O1—Pd1—C5164.02 (13)
C1—C8—H8A109.3C6—Pd1—C537.02 (13)
C7—C8—H8A109.3C2—Pd1—C581.56 (11)
C1—C8—H8B109.3C1—Pd1—C588.42 (9)
C8—C1—C2—C34.4 (5)C7—C6—Pd1—O2139.4 (2)
Pd1—C1—C2—C398.4 (3)C5—C6—Pd1—O1169.7 (2)
C8—C1—C2—Pd1102.8 (3)C7—C6—Pd1—O145.3 (4)
C1—C2—C3—C439.4 (4)C5—C6—Pd1—C265.00 (19)
Pd1—C2—C3—C440.9 (3)C7—C6—Pd1—C259.4 (2)
C2—C3—C4—C537.4 (4)C5—C6—Pd1—C198.4 (2)
C3—C4—C5—C694.4 (4)C7—C6—Pd1—C126.0 (2)
C3—C4—C5—Pd113.9 (4)C7—C6—Pd1—C5124.5 (3)
C4—C5—C6—C75.6 (5)C1—C2—Pd1—O2167.8 (2)
Pd1—C5—C6—C797.2 (3)C3—C2—Pd1—O244.2 (4)
C4—C5—C6—Pd1102.9 (3)C1—C2—Pd1—O193.72 (16)
C5—C6—C7—C836.9 (5)C3—C2—Pd1—O1142.7 (2)
Pd1—C6—C7—C843.0 (3)C1—C2—Pd1—C665.21 (17)
C2—C1—C8—C795.1 (4)C3—C2—Pd1—C658.4 (2)
Pd1—C1—C8—C714.4 (3)C3—C2—Pd1—C1123.6 (3)
C6—C7—C8—C139.4 (4)C1—C2—Pd1—C598.69 (18)
O1—C9—C10—C113.3 (5)C3—C2—Pd1—C524.9 (2)
C12—C9—C10—C11178.4 (3)C2—C1—Pd1—O2167.3 (2)
C9—C10—C11—O21.1 (5)C8—C1—Pd1—O246.1 (4)
C9—C10—C11—C13177.7 (3)C2—C1—Pd1—O186.03 (16)
C10—C9—O1—Pd10.7 (4)C8—C1—Pd1—O1152.8 (2)
C12—C9—O1—Pd1178.97 (19)C2—C1—Pd1—C6114.58 (17)
C10—C11—O2—Pd13.3 (4)C8—C1—Pd1—C66.6 (2)
C13—C11—O2—Pd1177.89 (19)C8—C1—Pd1—C2121.1 (3)
C11—O2—Pd1—O14.3 (2)C2—C1—Pd1—C578.01 (19)
C11—O2—Pd1—C6153.9 (2)C8—C1—Pd1—C543.1 (3)
C11—O2—Pd1—C2101.7 (3)C6—C5—Pd1—O283.27 (18)
C11—O2—Pd1—C1101.9 (3)C4—C5—Pd1—O2155.7 (2)
C11—O2—Pd1—C5169.3 (2)C6—C5—Pd1—O1166.1 (3)
C9—O1—Pd1—O22.4 (2)C4—C5—Pd1—O145.1 (4)
C9—O1—Pd1—C690.3 (3)C4—C5—Pd1—C6121.0 (3)
C9—O1—Pd1—C2163.3 (2)C6—C5—Pd1—C2114.74 (19)
C9—O1—Pd1—C1159.9 (3)C4—C5—Pd1—C26.3 (2)
C9—O1—Pd1—C5112.7 (3)C6—C5—Pd1—C178.3 (2)
C5—C6—Pd1—O296.14 (17)C4—C5—Pd1—C142.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···F010.992.383.209 (5)141
C2—H2···F02i12.523.222 (4)127
C6—H6···F04ii12.263.137 (4)146
C12—H12B···F04iii0.982.533.497 (3)169
C10—H10···F03iii0.952.423.320 (4)159
C13—H13B···F03iii0.982.533.435 (4)153
Symmetry codes: (i) x+1, y+1, z+1/2; (ii) x+1, y+2, z1/2; (iii) x+1/2, y+2, z.
(9Tth12_L) (thenoyltrifluoroacetonato)(η4-cyclo-octa-1,5-dienyl)palladium(II) hexafluorophosphate top
Crystal data top
C16H16F3O2PdS·F6PF(000) = 1144
Mr = 580.72Dx = 2.019 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10209 reflections
a = 9.9691 (2) Åθ = 2.2–33.0°
b = 17.0294 (3) ŵ = 1.26 mm1
c = 13.6427 (3) ÅT = 100 K
β = 124.439 (1)°Needle, orange
V = 1910.15 (7) Å30.35 × 0.2 × 0.1 mm
Z = 4
Data collection top
CCD area detector
diffractometer
4606 independent reflections
Radiation source: Enhance (Mo) X-ray Source3596 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 16.1829 pixels mm-1θmax = 28°, θmin = 2.2°
ω scansh = 1113
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 2221
Tmin = 0.667, Tmax = 0.884l = 1818
15058 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0366P)2]
where P = (Fo2 + 2Fc2)/3
4606 reflections(Δ/σ)max = 0.002
271 parametersΔρmax = 1.15 e Å3
0 restraintsΔρmin = 0.71 e Å3
Crystal data top
C16H16F3O2PdS·F6PV = 1910.15 (7) Å3
Mr = 580.72Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.9691 (2) ŵ = 1.26 mm1
b = 17.0294 (3) ÅT = 100 K
c = 13.6427 (3) Å0.35 × 0.2 × 0.1 mm
β = 124.439 (1)°
Data collection top
CCD area detector
diffractometer
4606 independent reflections
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
3596 reflections with I > 2σ(I)
Tmin = 0.667, Tmax = 0.884Rint = 0.024
15058 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.061H-atom parameters constrained
S = 1.01Δρmax = 1.15 e Å3
4606 reflectionsΔρmin = 0.71 e Å3
271 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6044 (2)0.77640 (12)0.32910 (19)0.0159 (5)
H10.55910.74660.36740.019*
C20.7142 (2)0.83430 (13)0.40058 (18)0.0146 (4)
H20.73460.83830.48110.018*
C30.8494 (3)0.86689 (13)0.39366 (19)0.0157 (5)
H3A0.94490.83170.43820.019*
H3B0.88160.91880.43320.019*
C40.8043 (3)0.87610 (13)0.26658 (19)0.0153 (5)
H4A0.87880.91460.26650.018*
H4B0.81930.82510.23910.018*
C50.6300 (3)0.90340 (12)0.18068 (18)0.0146 (4)
H50.61960.95610.14450.018*
C60.4995 (3)0.85390 (13)0.11038 (19)0.0159 (5)
H60.4120.87720.03240.019*
C70.5031 (3)0.76561 (13)0.11138 (19)0.0186 (5)
H7A0.54430.74750.0640.022*
H7B0.39060.74580.07220.022*
C80.6095 (3)0.72948 (13)0.23681 (19)0.0173 (5)
H8A0.57180.67530.23450.021*
H8B0.72340.72640.26060.021*
C90.3081 (2)0.94303 (12)0.35370 (18)0.0144 (4)
C100.2211 (2)0.99750 (13)0.26569 (19)0.0153 (4)
H100.14171.02730.26730.018*
C110.2410 (2)1.01279 (12)0.17182 (18)0.0131 (4)
C120.2724 (3)0.93220 (13)0.44707 (19)0.0162 (5)
C130.1421 (2)1.07354 (13)0.08575 (18)0.0141 (4)
C140.0167 (3)1.11729 (13)0.0749 (2)0.0165 (5)
H140.01941.11190.12580.02*
C150.0504 (3)1.17048 (13)0.0206 (2)0.0193 (5)
H150.13721.20530.04140.023*
C160.0227 (3)1.16667 (13)0.0801 (2)0.0197 (5)
H160.00771.19850.14680.024*
O10.42120 (18)0.89573 (9)0.37168 (13)0.0161 (3)
O20.33981 (17)0.97770 (8)0.15617 (12)0.0147 (3)
F011.19634 (16)0.93650 (8)0.82933 (12)0.0242 (3)
F10.20070 (16)0.86271 (8)0.43288 (12)0.0220 (3)
F021.02561 (16)0.85710 (8)0.67375 (12)0.0265 (3)
F20.17346 (16)0.98719 (8)0.44228 (12)0.0255 (3)
F30.40880 (15)0.93317 (8)0.55688 (11)0.0245 (3)
F031.24051 (17)0.80897 (8)0.67702 (12)0.0310 (3)
F041.40992 (16)0.88795 (8)0.83312 (13)0.0314 (4)
F051.19481 (17)0.93988 (8)0.66336 (12)0.0290 (3)
F061.23862 (18)0.80502 (8)0.84223 (12)0.0341 (4)
P011.21785 (7)0.87267 (3)0.75263 (5)0.01576 (13)
S10.17453 (7)1.09853 (3)0.02174 (5)0.01822 (12)
Pd10.491474 (19)0.891091 (10)0.260022 (14)0.01196 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0164 (11)0.0137 (11)0.0176 (11)0.0052 (8)0.0096 (9)0.0095 (9)
C20.0131 (10)0.0158 (11)0.0109 (10)0.0037 (8)0.0044 (9)0.0051 (8)
C30.0120 (10)0.0193 (11)0.0121 (10)0.0002 (8)0.0046 (9)0.0008 (8)
C40.0124 (10)0.0185 (12)0.0152 (11)0.0011 (8)0.0079 (9)0.0009 (8)
C50.0172 (11)0.0177 (12)0.0113 (10)0.0023 (8)0.0095 (9)0.0033 (8)
C60.0163 (11)0.0194 (12)0.0112 (10)0.0020 (9)0.0074 (9)0.0012 (8)
C70.0189 (11)0.0168 (12)0.0167 (11)0.0005 (9)0.0081 (10)0.0034 (9)
C80.0155 (11)0.0137 (11)0.0212 (12)0.0004 (8)0.0095 (10)0.0016 (9)
C90.0119 (10)0.0145 (11)0.0143 (11)0.0035 (8)0.0059 (9)0.0021 (8)
C100.0139 (11)0.0150 (11)0.0171 (11)0.0001 (8)0.0089 (9)0.0010 (9)
C110.0113 (10)0.0113 (10)0.0136 (10)0.0036 (8)0.0052 (9)0.0033 (8)
C120.0144 (11)0.0165 (11)0.0169 (11)0.0006 (9)0.0085 (9)0.0010 (9)
C130.0135 (10)0.0132 (11)0.0143 (11)0.0008 (8)0.0071 (9)0.0018 (8)
C140.0150 (11)0.0167 (11)0.0190 (11)0.0002 (9)0.0104 (10)0.0007 (9)
C150.0148 (11)0.0146 (11)0.0250 (12)0.0023 (9)0.0091 (10)0.0025 (9)
C160.0193 (11)0.0145 (11)0.0191 (11)0.0023 (9)0.0071 (10)0.0058 (9)
O10.0172 (8)0.0182 (8)0.0161 (8)0.0037 (6)0.0113 (7)0.0038 (6)
O20.0141 (7)0.0157 (8)0.0133 (8)0.0029 (6)0.0071 (6)0.0025 (6)
F010.0352 (8)0.0211 (7)0.0279 (7)0.0045 (6)0.0247 (7)0.0080 (6)
F10.0215 (7)0.0232 (7)0.0250 (7)0.0026 (5)0.0153 (6)0.0043 (6)
F020.0178 (7)0.0320 (8)0.0237 (8)0.0021 (6)0.0081 (6)0.0021 (6)
F20.0335 (8)0.0267 (8)0.0263 (8)0.0127 (6)0.0230 (7)0.0069 (6)
F30.0191 (7)0.0370 (8)0.0142 (7)0.0023 (6)0.0075 (6)0.0004 (6)
F030.0303 (8)0.0305 (8)0.0322 (8)0.0036 (6)0.0177 (7)0.0173 (6)
F040.0157 (7)0.0335 (8)0.0351 (9)0.0037 (6)0.0085 (7)0.0152 (7)
F050.0431 (9)0.0259 (8)0.0241 (8)0.0032 (7)0.0227 (7)0.0025 (6)
F060.0466 (9)0.0201 (8)0.0202 (7)0.0043 (6)0.0095 (7)0.0055 (6)
P010.0157 (3)0.0164 (3)0.0129 (3)0.0001 (2)0.0068 (2)0.0024 (2)
S10.0198 (3)0.0199 (3)0.0161 (3)0.0051 (2)0.0109 (2)0.0048 (2)
Pd10.01125 (9)0.01228 (9)0.01165 (9)0.00155 (6)0.00606 (7)0.00168 (6)
Geometric parameters (Å, º) top
C1—C21.384 (3)C9—C101.370 (3)
C1—C81.516 (3)C9—C121.515 (3)
C1—Pd12.184 (2)C10—C111.427 (3)
C1—H11C10—H100.95
C2—C31.509 (3)C11—O21.269 (2)
C2—Pd12.174 (2)C11—C131.453 (3)
C2—H21C12—F21.335 (2)
C3—C41.533 (3)C12—F31.338 (2)
C3—H3A0.99C12—F11.339 (2)
C3—H3B0.99C13—C141.390 (3)
C4—C51.519 (3)C13—S11.724 (2)
C4—H4A0.99C14—C151.407 (3)
C4—H4B0.99C14—H140.95
C5—C61.383 (3)C15—C161.365 (3)
C5—Pd12.194 (2)C15—H150.95
C5—H51C16—S11.705 (2)
C6—C71.504 (3)C16—H160.95
C6—Pd12.182 (2)O1—Pd12.0061 (15)
C6—H61O2—Pd12.0114 (14)
C7—C81.542 (3)F01—P011.6051 (14)
C7—H7A0.99F02—P011.6027 (14)
C7—H7B0.99F03—P011.5984 (14)
C8—H8A0.99F04—P011.6006 (14)
C8—H8B0.99F05—P011.5905 (14)
C9—O11.292 (2)F06—P011.6055 (14)
C2—C1—C8125.2 (2)O2—C11—C10125.48 (19)
C2—C1—Pd171.11 (12)O2—C11—C13115.83 (19)
C8—C1—Pd1111.36 (14)C10—C11—C13118.69 (19)
C2—C1—H1113.8F2—C12—F3107.53 (18)
C8—C1—H1113.8F2—C12—F1107.07 (17)
Pd1—C1—H1113.8F3—C12—F1107.12 (17)
C1—C2—C3126.7 (2)F2—C12—C9113.06 (18)
C1—C2—Pd171.87 (12)F3—C12—C9111.53 (17)
C3—C2—Pd1106.50 (13)F1—C12—C9110.24 (18)
C1—C2—H2114.2C14—C13—C11128.8 (2)
C3—C2—H2114.2C14—C13—S1111.55 (16)
Pd1—C2—H2114.2C11—C13—S1119.70 (16)
C2—C3—C4114.04 (18)C13—C14—C15111.8 (2)
C2—C3—H3A108.7C13—C14—H14124.1
C4—C3—H3A108.7C15—C14—H14124.1
C2—C3—H3B108.7C16—C15—C14112.7 (2)
C4—C3—H3B108.7C16—C15—H15123.7
H3A—C3—H3B107.6C14—C15—H15123.7
C5—C4—C3112.30 (18)C15—C16—S1112.71 (17)
C5—C4—H4A109.1C15—C16—H16123.6
C3—C4—H4A109.1S1—C16—H16123.6
C5—C4—H4B109.1C9—O1—Pd1121.52 (14)
C3—C4—H4B109.1C11—O2—Pd1124.93 (14)
H4A—C4—H4B107.9F05—P01—F0390.35 (8)
C6—C5—C4124.47 (19)F05—P01—F0490.40 (8)
C6—C5—Pd171.10 (13)F03—P01—F0490.13 (8)
C4—C5—Pd1110.79 (14)F05—P01—F0290.28 (8)
C6—C5—H5114.2F03—P01—F0290.36 (8)
C4—C5—H5114.2F04—P01—F02179.16 (9)
Pd1—C5—H5114.2F05—P01—F0189.84 (8)
C5—C6—C7126.5 (2)F03—P01—F01179.61 (9)
C5—C6—Pd172.06 (13)F04—P01—F0189.52 (8)
C7—C6—Pd1107.17 (15)F02—P01—F0189.99 (8)
C5—C6—H6114.1F05—P01—F06179.22 (9)
C7—C6—H6114.1F03—P01—F0690.00 (8)
Pd1—C6—H6114.1F04—P01—F0690.30 (8)
C6—C7—C8114.01 (18)F02—P01—F0689.02 (8)
C6—C7—H7A108.8F01—P01—F0689.82 (8)
C8—C7—H7A108.8C16—S1—C1391.23 (11)
C6—C7—H7B108.8O1—Pd1—O293.43 (6)
C8—C7—H7B108.8O1—Pd1—C288.22 (7)
H7A—C7—H7B107.6O2—Pd1—C2158.96 (7)
C1—C8—C7112.71 (18)O1—Pd1—C6159.28 (7)
C1—C8—H8A109O2—Pd1—C687.96 (7)
C7—C8—H8A109C2—Pd1—C697.84 (8)
C1—C8—H8B109O1—Pd1—C191.35 (7)
C7—C8—H8B109O2—Pd1—C1163.40 (7)
H8A—C8—H8B107.8C2—Pd1—C137.02 (8)
O1—C9—C10129.8 (2)C6—Pd1—C182.04 (8)
O1—C9—C12111.06 (18)O1—Pd1—C5163.42 (7)
C10—C9—C12119.11 (19)O2—Pd1—C590.84 (7)
C9—C10—C11124.8 (2)C2—Pd1—C582.16 (8)
C9—C10—H10117.6C6—Pd1—C536.84 (8)
C11—C10—H10117.6C1—Pd1—C589.06 (8)
C8—C1—C2—C35.9 (3)C9—O1—Pd1—C1161.65 (16)
Pd1—C1—C2—C397.4 (2)C9—O1—Pd1—C5107.1 (3)
C8—C1—C2—Pd1103.3 (2)C11—O2—Pd1—O11.77 (16)
C1—C2—C3—C438.1 (3)C11—O2—Pd1—C295.7 (2)
Pd1—C2—C3—C441.3 (2)C11—O2—Pd1—C6157.53 (17)
C2—C3—C4—C537.9 (3)C11—O2—Pd1—C1104.7 (3)
C3—C4—C5—C695.0 (2)C11—O2—Pd1—C5165.74 (16)
C3—C4—C5—Pd114.2 (2)C1—C2—Pd1—O194.61 (13)
C4—C5—C6—C74.3 (4)C3—C2—Pd1—O1141.46 (15)
Pd1—C5—C6—C798.4 (2)C1—C2—Pd1—O2170.45 (17)
C4—C5—C6—Pd1102.7 (2)C3—C2—Pd1—O246.5 (3)
C5—C6—C7—C840.9 (3)C1—C2—Pd1—C665.49 (14)
Pd1—C6—C7—C839.2 (2)C3—C2—Pd1—C658.44 (15)
C2—C1—C8—C793.7 (2)C3—C2—Pd1—C1123.9 (2)
Pd1—C1—C8—C712.3 (2)C1—C2—Pd1—C598.93 (14)
C6—C7—C8—C135.2 (3)C3—C2—Pd1—C525.00 (15)
O1—C9—C10—C110.0 (4)C5—C6—Pd1—O1171.57 (17)
C12—C9—C10—C11179.17 (19)C7—C6—Pd1—O147.9 (3)
C9—C10—C11—O20.9 (3)C5—C6—Pd1—O294.12 (13)
C9—C10—C11—C13178.8 (2)C7—C6—Pd1—O2142.21 (15)
O1—C9—C12—F2170.96 (17)C5—C6—Pd1—C265.58 (13)
C10—C9—C12—F29.7 (3)C7—C6—Pd1—C258.09 (15)
O1—C9—C12—F349.6 (2)C5—C6—Pd1—C199.16 (13)
C10—C9—C12—F3131.0 (2)C7—C6—Pd1—C124.51 (14)
O1—C9—C12—F169.2 (2)C7—C6—Pd1—C5123.7 (2)
C10—C9—C12—F1110.1 (2)C2—C1—Pd1—O185.24 (13)
O2—C11—C13—C14174.8 (2)C8—C1—Pd1—O1153.45 (15)
C10—C11—C13—C145.5 (3)C2—C1—Pd1—O2168.0 (2)
O2—C11—C13—S14.8 (3)C8—C1—Pd1—O246.7 (3)
C10—C11—C13—S1175.00 (15)C8—C1—Pd1—C2121.3 (2)
C11—C13—C14—C15179.7 (2)C2—C1—Pd1—C6114.47 (14)
S1—C13—C14—C150.1 (2)C8—C1—Pd1—C66.83 (15)
C13—C14—C15—C160.1 (3)C2—C1—Pd1—C578.18 (13)
C14—C15—C16—S10.0 (3)C8—C1—Pd1—C543.13 (15)
C10—C9—O1—Pd12.1 (3)C6—C5—Pd1—O1169.5 (2)
C12—C9—O1—Pd1177.19 (12)C4—C5—Pd1—O148.9 (3)
C10—C11—O2—Pd10.5 (3)C6—C5—Pd1—O285.48 (13)
C13—C11—O2—Pd1179.79 (13)C4—C5—Pd1—O2153.86 (14)
C15—C16—S1—C130.07 (18)C6—C5—Pd1—C2114.42 (14)
C14—C13—S1—C160.12 (17)C4—C5—Pd1—C26.23 (14)
C11—C13—S1—C16179.72 (17)C4—C5—Pd1—C6120.7 (2)
C9—O1—Pd1—O22.45 (16)C6—C5—Pd1—C177.92 (13)
C9—O1—Pd1—C2161.45 (16)C4—C5—Pd1—C142.74 (15)
C9—O1—Pd1—C690.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F20.952.332.712 (3)104
C14—H14···F01i0.952.323.193 (3)152
C5—H5···F01ii12.473.274 (3)137
C6—H6···F06iii12.483.175 (3)126
C15—H15···F03iv0.952.333.022 (3)129
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+2, y+2, z+1; (iii) x1, y, z1; (iv) x+1, y+1/2, z+1/2.
(10Rth7) (thenoyltrifluoroacetonato)(η4-cyclo-octa-1,5-dienyl)palladium(II) tetrafluoroborate top
Crystal data top
C16H16F3O2PdS·BF4F(000) = 1032
Mr = 522.56Dx = 1.942 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8114 reflections
a = 10.0528 (3) Åθ = 2.8–28.4°
b = 16.6333 (6) ŵ = 1.24 mm1
c = 13.1600 (3) ÅT = 100 K
β = 125.684 (2)°Cuboid, yellow
V = 1787.35 (9) Å30.28 × 0.16 × 0.11 mm
Z = 4
Data collection top
Bruker APEX-II 4K Kappa CCD
diffractometer
4464 independent reflections
Radiation source: sealed tube3873 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 512 pixels mm-1θmax = 28.4°, θmin = 3.1°
ϕ and ω scansh = 1213
Absorption correction: multi-scan
SADABS (Bruker, 2004)
k = 2222
Tmin = 0.724, Tmax = 0.876l = 1717
21884 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0339P)2 + 1.0448P]
where P = (Fo2 + 2Fc2)/3
4464 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.73 e Å3
Crystal data top
C16H16F3O2PdS·BF4V = 1787.35 (9) Å3
Mr = 522.56Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0528 (3) ŵ = 1.24 mm1
b = 16.6333 (6) ÅT = 100 K
c = 13.1600 (3) Å0.28 × 0.16 × 0.11 mm
β = 125.684 (2)°
Data collection top
Bruker APEX-II 4K Kappa CCD
diffractometer
4464 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2004)
3873 reflections with I > 2σ(I)
Tmin = 0.724, Tmax = 0.876Rint = 0.033
21884 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.071H-atom parameters constrained
S = 1.09Δρmax = 0.61 e Å3
4464 reflectionsΔρmin = 0.73 e Å3
253 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5698 (3)0.27486 (13)0.8290 (2)0.0144 (4)
H10.52840.250.87480.017*
C20.6994 (3)0.32719 (14)0.9005 (2)0.0148 (4)
H20.73390.33360.98840.018*
C30.8351 (3)0.34197 (14)0.8846 (2)0.0165 (5)
H3A0.84840.29360.84750.02*
H3B0.93930.35090.96780.02*
C40.7998 (3)0.41469 (15)0.8011 (2)0.0166 (5)
H4A0.83250.46410.85230.02*
H4B0.86850.41080.76990.02*
C50.6234 (3)0.42259 (15)0.6907 (2)0.0158 (5)
H50.59590.47510.64560.019*
C60.5166 (3)0.36048 (14)0.6193 (2)0.0155 (5)
H60.42520.37690.53240.019*
C70.5621 (3)0.27224 (15)0.6315 (2)0.0190 (5)
H7A0.67890.26770.66430.023*
H7B0.49610.2470.54770.023*
C80.5337 (3)0.22648 (15)0.7191 (2)0.0185 (5)
H8A0.41810.20860.67010.022*
H8B0.60350.17780.75050.022*
C90.2957 (3)0.44979 (13)0.8546 (2)0.0137 (4)
C100.2083 (3)0.50625 (13)0.7626 (2)0.0148 (4)
H100.12910.5370.76320.018*
C110.2289 (3)0.52149 (13)0.6666 (2)0.0127 (4)
C120.2617 (3)0.43797 (14)0.9529 (2)0.0147 (4)
C130.1291 (3)0.58218 (14)0.5719 (2)0.0136 (4)
C140.0021 (3)0.62730 (14)0.5509 (2)0.0168 (5)
H140.04260.62410.60040.02*
C150.0666 (3)0.67846 (14)0.4460 (2)0.0209 (5)
H150.15750.71310.41590.025*
C160.0157 (3)0.67274 (14)0.3923 (2)0.0211 (5)
H160.01080.70360.3220.025*
B010.1712 (3)0.63633 (17)0.7407 (3)0.0181 (5)
O10.4068 (2)0.40020 (9)0.87454 (15)0.0148 (3)
O20.33165 (19)0.48609 (9)0.65401 (15)0.0150 (3)
F010.00233 (17)0.64810 (9)0.80407 (14)0.0242 (3)
F10.40033 (16)0.44090 (9)1.06804 (12)0.0195 (3)
F20.19336 (17)0.36622 (8)0.93805 (13)0.0199 (3)
F020.25359 (18)0.70539 (9)0.67336 (14)0.0287 (3)
F030.2058 (2)0.62018 (10)0.82622 (15)0.0314 (4)
F30.16081 (17)0.49348 (9)0.94621 (13)0.0212 (3)
F040.21904 (18)0.57198 (9)0.65863 (13)0.0221 (3)
S10.17045 (8)0.60457 (4)0.46499 (6)0.01898 (13)
Pd10.479840 (19)0.396026 (10)0.761842 (15)0.01125 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0166 (11)0.0113 (11)0.0151 (11)0.0038 (8)0.0092 (10)0.0050 (9)
C20.0144 (11)0.0160 (11)0.0111 (11)0.0043 (9)0.0057 (9)0.0045 (9)
C30.0114 (10)0.0220 (12)0.0137 (11)0.0017 (9)0.0059 (9)0.0020 (9)
C40.0126 (11)0.0218 (12)0.0157 (12)0.0017 (9)0.0084 (10)0.0005 (10)
C50.0152 (11)0.0222 (12)0.0135 (11)0.0030 (9)0.0103 (10)0.0058 (9)
C60.0143 (11)0.0229 (13)0.0091 (11)0.0026 (9)0.0067 (9)0.0032 (9)
C70.0209 (12)0.0212 (13)0.0147 (12)0.0016 (10)0.0103 (10)0.0035 (10)
C80.0170 (11)0.0167 (12)0.0184 (12)0.0020 (9)0.0084 (10)0.0010 (10)
C90.0141 (10)0.0130 (11)0.0156 (11)0.0034 (8)0.0096 (9)0.0026 (9)
C100.0136 (10)0.0149 (11)0.0166 (11)0.0008 (9)0.0093 (9)0.0003 (9)
C110.0099 (10)0.0101 (10)0.0135 (11)0.0008 (8)0.0042 (9)0.0007 (8)
C120.0152 (11)0.0143 (11)0.0164 (11)0.0000 (9)0.0103 (10)0.0001 (9)
C130.0130 (10)0.0134 (11)0.0128 (11)0.0015 (8)0.0065 (9)0.0003 (9)
C140.0138 (11)0.0145 (11)0.0171 (12)0.0013 (9)0.0061 (10)0.0013 (9)
C150.0182 (12)0.0148 (12)0.0226 (13)0.0021 (9)0.0079 (11)0.0003 (10)
C160.0240 (13)0.0143 (12)0.0155 (12)0.0001 (10)0.0061 (11)0.0018 (9)
B010.0208 (13)0.0166 (13)0.0159 (13)0.0017 (11)0.0101 (12)0.0010 (11)
O10.0156 (8)0.0161 (8)0.0158 (8)0.0039 (6)0.0109 (7)0.0034 (6)
O20.0143 (8)0.0155 (8)0.0148 (8)0.0023 (6)0.0082 (7)0.0025 (6)
F010.0173 (7)0.0267 (8)0.0219 (8)0.0021 (6)0.0077 (6)0.0058 (6)
F10.0160 (7)0.0268 (8)0.0126 (7)0.0018 (6)0.0066 (6)0.0001 (6)
F20.0228 (7)0.0198 (7)0.0220 (8)0.0054 (6)0.0157 (7)0.0014 (6)
F020.0255 (8)0.0210 (8)0.0255 (8)0.0057 (6)0.0069 (7)0.0019 (6)
F030.0381 (9)0.0393 (9)0.0263 (9)0.0036 (7)0.0242 (8)0.0045 (7)
F30.0240 (7)0.0232 (8)0.0229 (8)0.0073 (6)0.0173 (7)0.0022 (6)
F040.0289 (8)0.0180 (7)0.0183 (7)0.0035 (6)0.0131 (7)0.0037 (6)
S10.0218 (3)0.0182 (3)0.0169 (3)0.0032 (2)0.0112 (3)0.0036 (2)
Pd10.01058 (9)0.01181 (10)0.01148 (10)0.00138 (6)0.00650 (8)0.00158 (6)
Geometric parameters (Å, º) top
C1—C21.382 (3)C9—O11.286 (3)
C1—C81.503 (3)C9—C101.371 (3)
C1—Pd12.174 (2)C9—C121.532 (3)
C1—H11C10—C111.416 (3)
C2—C31.516 (3)C10—H100.95
C2—Pd12.194 (2)C11—O21.282 (3)
C2—H21C11—C131.456 (3)
C3—C41.531 (3)C12—F11.333 (3)
C3—H3A0.99C12—F21.333 (3)
C3—H3B0.99C12—F31.336 (2)
C4—C51.506 (3)C13—C141.399 (3)
C4—H4A0.99C13—S11.724 (2)
C4—H4B0.99C14—C151.417 (3)
C5—C61.388 (3)C14—H140.95
C5—Pd12.174 (2)C15—C161.369 (3)
C5—H51C15—H150.95
C6—C71.518 (3)C16—S11.698 (3)
C6—Pd12.194 (2)C16—H160.95
C6—H61B01—F031.384 (3)
C7—C81.540 (3)B01—F021.391 (3)
C7—H7A0.99B01—F041.392 (3)
C7—H7B0.99B01—F011.402 (3)
C8—H8A0.99O1—Pd12.0032 (15)
C8—H8B0.99O2—Pd12.0028 (15)
C2—C1—C8126.6 (2)C10—C9—C12119.33 (19)
C2—C1—Pd172.33 (13)C9—C10—C11123.9 (2)
C8—C1—Pd1107.20 (15)C9—C10—H10118
C2—C1—H1114C11—C10—H10118
C8—C1—H1114O2—C11—C10125.6 (2)
Pd1—C1—H1114O2—C11—C13114.33 (19)
C1—C2—C3125.0 (2)C10—C11—C13120.11 (19)
C1—C2—Pd170.78 (13)F1—C12—F2107.87 (18)
C3—C2—Pd1110.49 (15)F1—C12—F3107.43 (18)
C1—C2—H2114.1F2—C12—F3107.61 (17)
C3—C2—H2114.1F1—C12—C9110.80 (17)
Pd1—C2—H2114.1F2—C12—C9109.94 (18)
C2—C3—C4112.16 (18)F3—C12—C9113.00 (18)
C2—C3—H3A109.2C14—C13—C11129.8 (2)
C4—C3—H3A109.2C14—C13—S1111.82 (17)
C2—C3—H3B109.2C11—C13—S1118.38 (16)
C4—C3—H3B109.2C13—C14—C15110.9 (2)
H3A—C3—H3B107.9C13—C14—H14124.5
C5—C4—C3114.25 (19)C15—C14—H14124.5
C5—C4—H4A108.7C16—C15—C14113.0 (2)
C3—C4—H4A108.7C16—C15—H15123.5
C5—C4—H4B108.7C14—C15—H15123.5
C3—C4—H4B108.7C15—C16—S1112.72 (19)
H4A—C4—H4B107.6C15—C16—H16123.6
C6—C5—C4126.8 (2)S1—C16—H16123.6
C6—C5—Pd172.23 (12)F03—B01—F02109.9 (2)
C4—C5—Pd1105.75 (14)F03—B01—F04110.2 (2)
C6—C5—H5114.3F02—B01—F04109.4 (2)
C4—C5—H5114.3F03—B01—F01109.6 (2)
Pd1—C5—H5114.3F02—B01—F01109.2 (2)
C5—C6—C7125.6 (2)F04—B01—F01108.62 (19)
C5—C6—Pd170.72 (12)C9—O1—Pd1121.37 (14)
C7—C6—Pd1111.15 (14)C11—O2—Pd1125.07 (14)
C5—C6—H6113.8C16—S1—C1391.52 (12)
C7—C6—H6113.8O2—Pd1—O193.23 (6)
Pd1—C6—H6113.8O2—Pd1—C1160.45 (8)
C6—C7—C8112.40 (18)O1—Pd1—C188.65 (7)
C6—C7—H7A109.1O2—Pd1—C587.08 (8)
C8—C7—H7A109.1O1—Pd1—C5158.94 (8)
C6—C7—H7B109.1C1—Pd1—C598.05 (9)
C8—C7—H7B109.1O2—Pd1—C691.28 (7)
H7A—C7—H7B107.9O1—Pd1—C6163.63 (8)
C1—C8—C7114.1 (2)C1—Pd1—C681.96 (8)
C1—C8—H8A108.7C5—Pd1—C637.05 (9)
C7—C8—H8A108.7O2—Pd1—C2162.05 (8)
C1—C8—H8B108.7O1—Pd1—C291.56 (7)
C7—C8—H8B108.7C1—Pd1—C236.89 (8)
H8A—C8—H8B107.6C5—Pd1—C282.31 (8)
O1—C9—C10130.8 (2)C6—Pd1—C288.94 (8)
O1—C9—C12109.90 (19)
C8—C1—C2—C33.4 (4)C11—O2—Pd1—C6160.73 (18)
Pd1—C1—C2—C3102.0 (2)C11—O2—Pd1—C2108.8 (3)
C8—C1—C2—Pd198.6 (2)C9—O1—Pd1—O21.83 (17)
C1—C2—C3—C494.5 (3)C9—O1—Pd1—C1158.70 (18)
Pd1—C2—C3—C414.2 (2)C9—O1—Pd1—C592.1 (3)
C2—C3—C4—C539.0 (3)C9—O1—Pd1—C6103.9 (3)
C3—C4—C5—C636.9 (3)C9—O1—Pd1—C2164.52 (17)
C3—C4—C5—Pd142.5 (2)C2—C1—Pd1—O2169.74 (18)
C4—C5—C6—C76.0 (3)C8—C1—Pd1—O246.0 (3)
Pd1—C5—C6—C7102.7 (2)C2—C1—Pd1—O194.40 (13)
C4—C5—C6—Pd196.7 (2)C8—C1—Pd1—O1141.84 (15)
C5—C6—C7—C893.6 (3)C2—C1—Pd1—C565.56 (14)
Pd1—C6—C7—C812.7 (2)C8—C1—Pd1—C558.20 (16)
C2—C1—C8—C740.5 (3)C2—C1—Pd1—C699.04 (14)
Pd1—C1—C8—C739.9 (2)C8—C1—Pd1—C624.72 (15)
C6—C7—C8—C135.9 (3)C8—C1—Pd1—C2123.8 (2)
O1—C9—C10—C110.9 (4)C6—C5—Pd1—O296.00 (14)
C12—C9—C10—C11179.4 (2)C4—C5—Pd1—O2139.72 (16)
C9—C10—C11—O21.0 (4)C6—C5—Pd1—O1172.58 (18)
C9—C10—C11—C13179.4 (2)C4—C5—Pd1—O148.3 (3)
O1—C9—C12—F152.3 (2)C6—C5—Pd1—C165.04 (15)
C10—C9—C12—F1128.9 (2)C4—C5—Pd1—C159.24 (17)
O1—C9—C12—F266.8 (2)C4—C5—Pd1—C6124.3 (2)
C10—C9—C12—F2112.0 (2)C6—C5—Pd1—C298.51 (15)
O1—C9—C12—F3172.96 (18)C4—C5—Pd1—C225.77 (16)
C10—C9—C12—F38.3 (3)C5—C6—Pd1—O283.45 (14)
O2—C11—C13—C14174.3 (2)C7—C6—Pd1—O2154.86 (16)
C10—C11—C13—C146.1 (4)C5—C6—Pd1—O1170.5 (2)
O2—C11—C13—S15.0 (3)C7—C6—Pd1—O148.8 (3)
C10—C11—C13—S1174.60 (17)C5—C6—Pd1—C1114.96 (15)
C11—C13—C14—C15178.6 (2)C7—C6—Pd1—C16.73 (16)
S1—C13—C14—C150.8 (3)C7—C6—Pd1—C5121.7 (2)
C13—C14—C15—C161.1 (3)C5—C6—Pd1—C278.60 (14)
C14—C15—C16—S11.0 (3)C7—C6—Pd1—C243.09 (16)
C10—C9—O1—Pd10.1 (3)C1—C2—Pd1—O2168.8 (2)
C12—C9—O1—Pd1178.45 (13)C3—C2—Pd1—O247.6 (3)
C10—C11—O2—Pd13.6 (3)C1—C2—Pd1—O185.67 (13)
C13—C11—O2—Pd1176.77 (14)C3—C2—Pd1—O1153.07 (16)
C15—C16—S1—C130.5 (2)C3—C2—Pd1—C1121.3 (2)
C14—C13—S1—C160.19 (19)C1—C2—Pd1—C5114.55 (14)
C11—C13—S1—C16179.27 (19)C3—C2—Pd1—C56.71 (16)
C11—O2—Pd1—O13.53 (18)C1—C2—Pd1—C677.97 (14)
C11—O2—Pd1—C191.5 (3)C3—C2—Pd1—C643.30 (17)
C11—O2—Pd1—C5162.45 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F010.952.513.420 (3)162
C10—H10···F30.952.352.731 (2)103
C14—H14···F010.952.53.351 (3)149
C14—H14···F040.952.463.349 (3)155
C2—H2···F01i12.53.278 (3)135
C3—H3B···F03i0.992.513.496 (3)177
C5—H5···F04ii12.393.106 (3)128
C6—H6···F04iii12.293.290 (3)174
C16—H16···F01iv0.952.483.165 (3)129
C16—H16···F02iv0.952.553.262 (3)132
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y, z; (iii) x, y+1, z+1; (iv) x, y+3/2, z1/2.
(10ath3_0m) (hexafluoroacetylacetonato)(η4-cyclo-octa-1,5-dienyl)palladium(II) hexafluorophosphate top
Crystal data top
C13H13F6O2Pd·F6PF(000) = 1104
Mr = 566.6Dx = 2.128 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8161 reflections
a = 8.5885 (2) Åθ = 2.8–32.6°
b = 10.6304 (2) ŵ = 1.27 mm1
c = 19.4093 (4) ÅT = 100 K
β = 93.415 (1)°Plate, yellow
V = 1768.91 (6) Å30.38 × 0.22 × 0.07 mm
Z = 4
Data collection top
Bruker APEX-II 4K Kappa CCD
diffractometer
4248 independent reflections
Radiation source: sealed tube3805 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 512 pixels mm-1θmax = 28°, θmin = 2.4°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
SADABS (Bruker, 2004)
k = 1413
Tmin = 0.644, Tmax = 0.916l = 2525
16999 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0249P)2 + 2.P]
where P = (Fo2 + 2Fc2)/3
4248 reflections(Δ/σ)max = 0.001
295 parametersΔρmax = 0.60 e Å3
1 restraintΔρmin = 0.65 e Å3
Crystal data top
C13H13F6O2Pd·F6PV = 1768.91 (6) Å3
Mr = 566.6Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.5885 (2) ŵ = 1.27 mm1
b = 10.6304 (2) ÅT = 100 K
c = 19.4093 (4) Å0.38 × 0.22 × 0.07 mm
β = 93.415 (1)°
Data collection top
Bruker APEX-II 4K Kappa CCD
diffractometer
4248 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2004)
3805 reflections with I > 2σ(I)
Tmin = 0.644, Tmax = 0.916Rint = 0.029
16999 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0251 restraint
wR(F2) = 0.062H-atom parameters constrained
S = 1.07Δρmax = 0.60 e Å3
4248 reflectionsΔρmin = 0.65 e Å3
295 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 > 2σ(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. A three-part disorder was observed for a CF3 moiety (C13, F4—F6).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.4159 (3)0.0840 (2)0.29214 (11)0.0193 (4)
H10.49430.14650.27740.023*
C20.2635 (3)0.1129 (2)0.27037 (11)0.0204 (4)
H20.25270.19170.24240.024*
C30.1305 (3)0.0219 (2)0.25781 (11)0.0236 (5)
H3A0.13560.01420.2110.028*
H3B0.03090.06840.25920.028*
C40.1312 (3)0.0856 (2)0.31034 (12)0.0245 (5)
H4A0.02530.12230.31040.029*
H4B0.20320.15230.29630.029*
C50.1811 (3)0.0420 (2)0.38289 (11)0.0204 (4)
H50.0980.04990.41660.024*
C60.3315 (3)0.0484 (2)0.41255 (12)0.0208 (4)
H60.33710.06110.46370.025*
C70.4755 (3)0.0901 (2)0.37814 (13)0.0239 (5)
H7A0.48130.18310.37970.029*
H7B0.56850.05680.40470.029*
C80.4806 (3)0.0473 (2)0.30292 (12)0.0232 (5)
H8A0.58990.04930.28930.028*
H8B0.41940.10670.27280.028*
C90.2922 (2)0.4149 (2)0.40118 (11)0.0179 (4)
C100.2408 (3)0.4066 (2)0.46716 (12)0.0206 (4)
H100.22160.48230.49130.025*
C110.2159 (2)0.2923 (2)0.49978 (11)0.0183 (4)
C120.3198 (3)0.5460 (2)0.37152 (13)0.0251 (5)
C130.1586 (3)0.2993 (2)0.57296 (12)0.0234 (5)
O10.31948 (18)0.32899 (14)0.35832 (8)0.0184 (3)
O20.23469 (18)0.18173 (15)0.47876 (8)0.0187 (3)
F010.1961 (3)0.3528 (2)0.42928 (14)0.0760 (8)
F020.1072 (2)0.1628 (3)0.46033 (11)0.0798 (9)
F030.03143 (16)0.25360 (14)0.36249 (8)0.0303 (3)
F040.28470 (19)0.2749 (2)0.32642 (9)0.0526 (5)
F050.36114 (16)0.18714 (16)0.42473 (8)0.0312 (3)
F060.1929 (2)0.08614 (17)0.35887 (13)0.0636 (6)
P010.19615 (7)0.22092 (6)0.39388 (3)0.01978 (12)
Pd10.288665 (19)0.144660 (15)0.380626 (8)0.01539 (6)
F30.3059 (2)0.63734 (14)0.41678 (9)0.0426 (4)
F10.46128 (19)0.55329 (15)0.34792 (9)0.0413 (4)
F20.2197 (2)0.56862 (16)0.31814 (10)0.0510 (5)
F40.2685 (3)0.3564 (3)0.61449 (10)0.0331 (7)0.757 (6)
F50.0308 (3)0.3603 (5)0.57533 (13)0.0448 (10)0.757 (6)
F60.1453 (5)0.1845 (2)0.59988 (13)0.0401 (8)0.757 (6)
F4B0.254 (2)0.295 (2)0.6198 (7)0.0331 (7)0.115 (4)
F5B0.0035 (16)0.281 (3)0.5731 (8)0.024 (4)0.115 (4)
F6B0.180 (3)0.4104 (14)0.6067 (8)0.0401 (8)0.115 (4)
F4C0.2190 (17)0.2251 (19)0.6177 (6)0.0331 (7)0.128 (4)
F5C0.039 (4)0.2199 (18)0.5798 (11)0.048 (7)0.128 (4)
F6C0.068 (3)0.4122 (15)0.5823 (10)0.0401 (8)0.128 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0252 (11)0.0215 (11)0.0120 (10)0.0032 (9)0.0067 (8)0.0021 (8)
C20.0283 (11)0.0254 (11)0.0075 (9)0.0001 (9)0.0029 (8)0.0020 (8)
C30.0237 (11)0.0331 (13)0.0138 (10)0.0022 (9)0.0011 (9)0.0051 (9)
C40.0259 (11)0.0310 (13)0.0169 (11)0.0103 (10)0.0045 (9)0.0046 (9)
C50.0252 (11)0.0210 (11)0.0155 (10)0.0088 (9)0.0054 (8)0.0011 (8)
C60.0314 (12)0.0147 (10)0.0161 (10)0.0036 (9)0.0002 (9)0.0025 (8)
C70.0262 (11)0.0175 (11)0.0275 (12)0.0005 (9)0.0017 (9)0.0011 (9)
C80.0224 (11)0.0225 (11)0.0252 (12)0.0005 (9)0.0044 (9)0.0053 (9)
C90.0163 (10)0.0192 (10)0.0181 (10)0.0015 (8)0.0004 (8)0.0001 (8)
C100.0233 (11)0.0196 (11)0.0195 (11)0.0028 (8)0.0043 (9)0.0043 (9)
C110.0170 (10)0.0248 (11)0.0131 (10)0.0034 (8)0.0014 (8)0.0020 (8)
C120.0309 (12)0.0205 (11)0.0245 (12)0.0038 (9)0.0069 (10)0.0002 (9)
C130.0285 (12)0.0256 (12)0.0162 (11)0.0054 (9)0.0040 (9)0.0036 (9)
O10.0239 (8)0.0178 (7)0.0138 (7)0.0003 (6)0.0032 (6)0.0009 (6)
O20.0252 (8)0.0198 (7)0.0112 (7)0.0021 (6)0.0010 (6)0.0010 (6)
F010.0679 (14)0.0589 (14)0.106 (2)0.0280 (11)0.0448 (13)0.0577 (13)
F020.0312 (10)0.159 (3)0.0480 (12)0.0065 (12)0.0068 (9)0.0616 (14)
F030.0228 (7)0.0382 (8)0.0300 (8)0.0049 (6)0.0033 (6)0.0037 (7)
F040.0308 (9)0.0821 (14)0.0433 (10)0.0123 (9)0.0100 (7)0.0405 (10)
F050.0228 (7)0.0443 (9)0.0267 (8)0.0028 (6)0.0033 (6)0.0075 (7)
F060.0633 (13)0.0298 (9)0.1020 (17)0.0129 (9)0.0402 (12)0.0194 (10)
P010.0194 (3)0.0231 (3)0.0167 (3)0.0017 (2)0.0008 (2)0.0011 (2)
Pd10.02091 (9)0.01564 (9)0.00963 (9)0.00119 (6)0.00091 (6)0.00051 (6)
F30.0685 (12)0.0196 (8)0.0425 (10)0.0097 (7)0.0276 (9)0.0063 (7)
F10.0412 (9)0.0323 (9)0.0533 (11)0.0077 (7)0.0272 (8)0.0052 (8)
F20.0666 (12)0.0335 (9)0.0502 (11)0.0021 (8)0.0198 (9)0.0200 (8)
F40.0376 (12)0.0486 (18)0.0129 (9)0.0169 (12)0.0000 (7)0.0074 (10)
F50.0292 (17)0.081 (3)0.0251 (13)0.0207 (19)0.0082 (11)0.0037 (18)
F60.073 (2)0.0258 (12)0.0251 (12)0.0095 (15)0.0293 (14)0.0015 (10)
F4B0.0376 (12)0.0486 (18)0.0129 (9)0.0169 (12)0.0000 (7)0.0074 (10)
F5B0.005 (6)0.044 (12)0.022 (7)0.003 (7)0.004 (4)0.013 (9)
F6B0.073 (2)0.0258 (12)0.0251 (12)0.0095 (15)0.0293 (14)0.0015 (10)
F4C0.0376 (12)0.0486 (18)0.0129 (9)0.0169 (12)0.0000 (7)0.0074 (10)
F5C0.093 (18)0.017 (9)0.040 (11)0.022 (9)0.059 (12)0.017 (8)
F6C0.073 (2)0.0258 (12)0.0251 (12)0.0095 (15)0.0293 (14)0.0015 (10)
Geometric parameters (Å, º) top
C1—C21.386 (3)C9—C121.531 (3)
C1—C81.512 (3)C10—C111.393 (3)
C1—Pd12.187 (2)C10—H100.95
C1—H11C11—O21.258 (3)
C2—C31.505 (3)C11—C131.533 (3)
C2—Pd12.164 (2)C12—F31.320 (3)
C2—H21C12—F11.326 (3)
C3—C41.531 (3)C12—F21.329 (3)
C3—H3A0.99C13—F4B1.186 (16)
C3—H3B0.99C13—F4C1.262 (14)
C4—C51.520 (3)C13—F51.277 (4)
C4—H4A0.99C13—F61.335 (4)
C4—H4B0.99C13—F5C1.344 (18)
C5—C61.384 (3)C13—F41.348 (3)
C5—Pd12.190 (2)C13—F6B1.357 (15)
C5—H51C13—F5B1.407 (14)
C6—C71.507 (3)C13—F6C1.45 (2)
C6—Pd12.169 (2)O1—Pd12.0275 (15)
C6—H61O2—Pd12.0257 (15)
C7—C81.532 (3)F01—P011.5610 (19)
C7—H7A0.99F02—P011.5852 (18)
C7—H7B0.99F03—P011.6112 (15)
C8—H8A0.99F04—P011.5820 (16)
C8—H8B0.99F05—P011.6114 (15)
C9—O11.267 (3)F06—P011.5867 (19)
C9—C101.382 (3)
C2—C1—C8125.4 (2)F4C—C13—F5C79.9 (15)
C2—C1—Pd170.55 (12)F5—C13—F5C69.6 (13)
C8—C1—Pd1111.12 (15)F6—C13—F5C45.8 (14)
C2—C1—H1113.9F4B—C13—F429.8 (12)
C8—C1—H1113.9F4C—C13—F468.0 (9)
Pd1—C1—H1113.9F5—C13—F4108.8 (3)
C1—C2—C3126.9 (2)F6—C13—F4104.5 (2)
C1—C2—Pd172.32 (12)F5C—C13—F4137.4 (10)
C3—C2—Pd1106.91 (14)F4B—C13—F6B66.1 (14)
C1—C2—H2114F4C—C13—F6B100.0 (11)
C3—C2—H2114F5—C13—F6B68.5 (11)
Pd1—C2—H2114F6—C13—F6B128.2 (7)
C2—C3—C4113.51 (18)F5C—C13—F6B125.6 (10)
C2—C3—H3A108.9F4—C13—F6B41.4 (11)
C4—C3—H3A108.9F4B—C13—F5B129.1 (11)
C2—C3—H3B108.9F4C—C13—F5B106.1 (11)
C4—C3—H3B108.9F5—C13—F5B38.7 (11)
H3A—C3—H3B107.7F6—C13—F5B76.2 (11)
C5—C4—C3112.27 (19)F5C—C13—F5B31.5 (11)
C5—C4—H4A109.1F4—C13—F5B136.1 (8)
C3—C4—H4A109.1F6B—C13—F5B103.2 (12)
C5—C4—H4B109.1F4B—C13—F6C106.5 (13)
C3—C4—H4B109.1F4C—C13—F6C129.4 (10)
H4A—C4—H4B107.9F5—C13—F6C26.7 (9)
C6—C5—C4125.1 (2)F6—C13—F6C130.6 (7)
C6—C5—Pd170.67 (12)F5C—C13—F6C95.2 (13)
C4—C5—Pd1110.72 (15)F4—C13—F6C85.0 (10)
C6—C5—H5114.1F6B—C13—F6C43.6 (10)
C4—C5—H5114.1F5B—C13—F6C65.1 (12)
Pd1—C5—H5114.1F4B—C13—C11117.6 (8)
C5—C6—C7126.9 (2)F4C—C13—C11117.8 (6)
C5—C6—Pd172.30 (13)F5—C13—C11112.5 (2)
C7—C6—Pd1106.36 (14)F6—C13—C11111.0 (2)
C5—C6—H6114.1F5C—C13—C11110.6 (7)
C7—C6—H6114.1F4—C13—C11108.9 (2)
Pd1—C6—H6114.1F6B—C13—C11116.6 (6)
C6—C7—C8113.94 (19)F5B—C13—C11111.6 (6)
C6—C7—H7A108.8F6C—C13—C11111.1 (7)
C8—C7—H7A108.8C9—O1—Pd1121.67 (14)
C6—C7—H7B108.8C11—O2—Pd1121.85 (14)
C8—C7—H7B108.8F01—P01—F0491.50 (15)
H7A—C7—H7B107.7F01—P01—F0290.26 (16)
C1—C8—C7112.02 (19)F04—P01—F02178.23 (15)
C1—C8—H8A109.2F01—P01—F06178.78 (15)
C7—C8—H8A109.2F04—P01—F0689.59 (13)
C1—C8—H8B109.2F02—P01—F0688.65 (15)
C7—C8—H8B109.2F01—P01—F0389.76 (10)
H8A—C8—H8B107.9F04—P01—F0389.91 (8)
O1—C9—C10130.1 (2)F02—P01—F0390.00 (9)
O1—C9—C12111.73 (19)F06—P01—F0389.69 (9)
C10—C9—C12118.1 (2)F01—P01—F0590.77 (10)
C9—C10—C11122.9 (2)F04—P01—F0589.91 (8)
C9—C10—H10118.6F02—P01—F0590.16 (9)
C11—C10—H10118.6F06—P01—F0589.78 (10)
O2—C11—C10129.9 (2)F03—P01—F05179.44 (9)
O2—C11—C13113.63 (19)O2—Pd1—O193.03 (6)
C10—C11—C13116.4 (2)O2—Pd1—C2160.90 (8)
F3—C12—F1107.9 (2)O1—Pd1—C286.93 (8)
F3—C12—F2107.8 (2)O2—Pd1—C687.70 (8)
F1—C12—F2106.5 (2)O1—Pd1—C6162.45 (8)
F3—C12—C9113.4 (2)C2—Pd1—C698.05 (9)
F1—C12—C9110.4 (2)O2—Pd1—C1161.58 (7)
F2—C12—C9110.52 (19)O1—Pd1—C192.27 (7)
F4B—C13—F4C38.2 (10)C2—Pd1—C137.14 (8)
F4B—C13—F5123.0 (9)C6—Pd1—C182.01 (9)
F4C—C13—F5127.7 (6)O2—Pd1—C592.11 (7)
F4B—C13—F674.8 (12)O1—Pd1—C5160.11 (8)
F4C—C13—F636.9 (8)C2—Pd1—C582.01 (8)
F5—C13—F6110.8 (3)C6—Pd1—C537.03 (8)
F4B—C13—F5C113.4 (15)C1—Pd1—C588.84 (8)
C8—C1—C2—C34.4 (4)C13—C11—O2—Pd1173.76 (13)
Pd1—C1—C2—C398.2 (2)C11—O2—Pd1—O17.48 (17)
C8—C1—C2—Pd1102.6 (2)C11—O2—Pd1—C281.9 (3)
C1—C2—C3—C438.5 (3)C11—O2—Pd1—C6169.93 (17)
Pd1—C2—C3—C441.8 (2)C11—O2—Pd1—C1114.0 (3)
C2—C3—C4—C538.2 (3)C11—O2—Pd1—C5153.30 (17)
C3—C4—C5—C694.7 (3)C9—O1—Pd1—O24.52 (16)
C3—C4—C5—Pd114.3 (2)C9—O1—Pd1—C2156.36 (17)
C4—C5—C6—C74.7 (4)C9—O1—Pd1—C696.5 (3)
Pd1—C5—C6—C797.5 (2)C9—O1—Pd1—C1166.88 (17)
C4—C5—C6—Pd1102.2 (2)C9—O1—Pd1—C5100.3 (3)
C5—C6—C7—C838.1 (3)C1—C2—Pd1—O2171.75 (19)
Pd1—C6—C7—C841.8 (2)C3—C2—Pd1—O247.5 (3)
C2—C1—C8—C794.5 (3)C1—C2—Pd1—O197.86 (14)
Pd1—C1—C8—C713.9 (2)C3—C2—Pd1—O1137.94 (16)
C6—C7—C8—C138.1 (3)C1—C2—Pd1—C665.22 (14)
O1—C9—C10—C113.1 (4)C3—C2—Pd1—C658.98 (17)
C12—C9—C10—C11178.3 (2)C3—C2—Pd1—C1124.2 (2)
C9—C10—C11—O20.8 (4)C1—C2—Pd1—C598.71 (14)
C9—C10—C11—C13179.9 (2)C3—C2—Pd1—C525.49 (16)
O1—C9—C12—F3174.4 (2)C5—C6—Pd1—O296.58 (13)
C10—C9—C12—F36.8 (3)C7—C6—Pd1—O2139.15 (15)
O1—C9—C12—F153.1 (3)C5—C6—Pd1—O1170.6 (2)
C10—C9—C12—F1128.0 (2)C7—C6—Pd1—O146.4 (3)
O1—C9—C12—F264.5 (3)C5—C6—Pd1—C265.13 (14)
C10—C9—C12—F2114.4 (2)C7—C6—Pd1—C259.14 (16)
O2—C11—C13—F4B85.3 (14)C5—C6—Pd1—C198.74 (14)
C10—C11—C13—F4B94.1 (14)C7—C6—Pd1—C125.53 (15)
O2—C11—C13—F4C41.9 (10)C7—C6—Pd1—C5124.3 (2)
C10—C11—C13—F4C137.4 (10)C2—C1—Pd1—O2171.5 (2)
O2—C11—C13—F5122.9 (3)C8—C1—Pd1—O250.0 (3)
C10—C11—C13—F557.8 (4)C2—C1—Pd1—O181.88 (14)
O2—C11—C13—F61.9 (3)C8—C1—Pd1—O1156.63 (15)
C10—C11—C13—F6177.4 (3)C8—C1—Pd1—C2121.5 (2)
O2—C11—C13—F5C47.2 (16)C2—C1—Pd1—C6114.79 (14)
C10—C11—C13—F5C133.4 (16)C8—C1—Pd1—C66.70 (15)
O2—C11—C13—F4116.4 (2)C2—C1—Pd1—C578.26 (14)
C10—C11—C13—F462.9 (3)C8—C1—Pd1—C543.23 (16)
O2—C11—C13—F6B160.8 (13)C6—C5—Pd1—O283.36 (13)
C10—C11—C13—F6B18.6 (13)C4—C5—Pd1—O2155.39 (16)
O2—C11—C13—F5B81.0 (13)C6—C5—Pd1—O1171.71 (19)
C10—C11—C13—F5B99.6 (13)C4—C5—Pd1—O150.5 (3)
O2—C11—C13—F6C151.6 (11)C6—C5—Pd1—C2114.89 (14)
C10—C11—C13—F6C29.0 (11)C4—C5—Pd1—C26.36 (16)
C10—C9—O1—Pd10.3 (3)C4—C5—Pd1—C6121.2 (2)
C12—C9—O1—Pd1178.37 (14)C6—C5—Pd1—C178.24 (14)
C10—C11—O2—Pd17.0 (3)C4—C5—Pd1—C143.01 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···F06i0.992.743.448 (3)129
C1—H1···F04i12.483.312 (3)140
C2—H2···F4Bii12.383.078 (16)126
C2—H2···F4Cii12.583.429 (15)143
C3—H3A···F6Bii0.992.363.075 (14)129
C3—H3B···F2iii0.992.553.307 (3)133
C8—H8B···F04iii0.992.523.493 (3)167
C4—H4A···F6iv0.992.433.205 (4)134
C5—H5···F5Civ12.162.798 (15)120
C6—H6···F05iv12.543.481 (3)156
C7—H7A···F3v0.992.563.348 (3)136
C10—H10···F01vi0.952.353.289 (3)168
C10—H10···F30.952.342.711 (3)103
Symmetry codes: (i) x+1, y, z; (ii) x, y+1/2, z1/2; (iii) x, y1/2, z+1/2; (iv) x, y, z+1; (v) x, y1, z; (vi) x, y+1, z+1.

Experimental details

(8Fth3)(10rth5_0ma)(9Tth12_L)(10Rth7)
Crystal data
Chemical formulaC13H19O2Pd·F6PC13H19O2Pd·BF4C16H16F3O2PdS·F6PC16H16F3O2PdS·BF4
Mr458.65400.49580.72522.56
Crystal system, space groupMonoclinic, P21/cOrthorhombic, Pca21Monoclinic, P21/cMonoclinic, P21/c
Temperature (K)100100100100
a, b, c (Å)9.3166 (6), 15.4676 (8), 12.6132 (6)26.2908 (11), 7.1684 (3), 7.7782 (3)9.9691 (2), 17.0294 (3), 13.6427 (3)10.0528 (3), 16.6333 (6), 13.1600 (3)
α, β, γ (°)90, 119.016 (4), 9090, 90, 9090, 124.439 (1), 9090, 125.684 (2), 90
V3)1589.49 (15)1465.90 (10)1910.15 (7)1787.35 (9)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)1.341.311.261.24
Crystal size (mm)0.13 × 0.07 × 0.030.34 × 0.1 × 0.070.35 × 0.2 × 0.10.28 × 0.16 × 0.11
Data collection
DiffractometerBruker X8 Apex II 4K Kappa CCD
diffractometer
Bruker X8 APEX-II 4K Kappa CCD
diffractometer
CCD area detector
diffractometer
Bruker APEX-II 4K Kappa CCD
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 2004)
Multi-scan
SADABS (Bruker, 2004)
Multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Multi-scan
SADABS (Bruker, 2004)
Tmin, Tmax0.846, 0.9610.664, 0.9140.667, 0.8840.724, 0.876
No. of measured, independent and
observed [I > 2σ(I)] reflections
10747, 3952, 3112 15654, 3117, 2960 15058, 4606, 3596 21884, 4464, 3873
Rint0.0410.0250.0240.033
(sin θ/λ)max1)0.6670.6690.6610.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.081, 1.05 0.022, 0.062, 0.93 0.025, 0.061, 1.01 0.027, 0.071, 1.09
No. of reflections3952311746064464
No. of parameters210192271253
No. of restraints0100
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.70, 0.671.05, 0.611.15, 0.710.61, 0.73
Absolute structure?Flack H D (1983), Acta Cryst. A39, 876-881, 1143 Friedel pairs??
Absolute structure parameter?0.01 (3)??


(10ath3_0m)
Crystal data
Chemical formulaC13H13F6O2Pd·F6P
Mr566.6
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)8.5885 (2), 10.6304 (2), 19.4093 (4)
α, β, γ (°)90, 93.415 (1), 90
V3)1768.91 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.27
Crystal size (mm)0.38 × 0.22 × 0.07
Data collection
DiffractometerBruker APEX-II 4K Kappa CCD
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 2004)
Tmin, Tmax0.644, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections
16999, 4248, 3805
Rint0.029
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.062, 1.07
No. of reflections4248
No. of parameters295
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.60, 0.65
Absolute structure?
Absolute structure parameter?

Computer programs: Bruker APEX2 (Bruker, 2005), CrysAlis CCD (Oxford Diffraction, 2006), Bruker SAINT-Plus (Bruker, 2004), CrysAlis RED (Oxford Diffraction, 2006), Bruker SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND 3.0c (Brandenburg & Putz, 2005), DIAMOND 3.0c (Brandenburg & Putz, 2004), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) for (8Fth3) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F60.952.393.295 (4)158.7
C7—H7A···F4i0.992.473.311 (4)143.1
C2—H2···F6ii12.523.366 (4)141.9
C2—H2···F3ii12.543.257 (4)128.9
C5—H5···F3iii12.363.142 (4)134.9
C8—H8A···F1iv0.992.533.481 (4)160.6
C6—H6···F1v12.453.242 (3)135.9
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z; (iii) x+1, y+1/2, z+1/2; (iv) x+2, y+1/2, z+1/2; (v) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) for (10rth5_0ma) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···F010.992.383.209 (5)141.2
C2—H2···F02i12.523.222 (4)126.7
C6—H6···F04ii12.263.137 (4)145.8
C12—H12B···F04iii0.982.533.497 (3)169.2
C10—H10···F03iii0.952.423.320 (4)158.9
C13—H13B···F03iii0.982.533.435 (4)153.2
Symmetry codes: (i) x+1, y+1, z+1/2; (ii) x+1, y+2, z1/2; (iii) x+1/2, y+2, z.
Hydrogen-bond geometry (Å, º) for (9Tth12_L) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F20.952.332.712 (3)103.6
C14—H14···F01i0.952.323.193 (3)152.3
C5—H5···F01ii12.473.274 (3)137
C6—H6···F06iii12.483.175 (3)126
C15—H15···F03iv0.952.333.022 (3)128.9
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+2, y+2, z+1; (iii) x1, y, z1; (iv) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (10Rth7) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F010.952.513.420 (3)161.5
C10—H10···F30.952.352.731 (2)103.3
C14—H14···F010.952.53.351 (3)149.4
C14—H14···F040.952.463.349 (3)155.2
C2—H2···F01i12.53.278 (3)134.6
C3—H3B···F03i0.992.513.496 (3)177
C5—H5···F04ii12.393.106 (3)127.8
C6—H6···F04iii12.293.290 (3)173.9
C16—H16···F01iv0.952.483.165 (3)128.5
C16—H16···F02iv0.952.553.262 (3)131.8
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y, z; (iii) x, y+1, z+1; (iv) x, y+3/2, z1/2.
Hydrogen-bond geometry (Å, º) for (10ath3_0m) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···F06i0.992.743.448 (3)128.7
C1—H1···F04i12.483.312 (3)140.2
C2—H2···F4Bii12.383.078 (16)125.8
C2—H2···F4Cii12.583.429 (15)143
C3—H3A···F6Bii0.992.363.075 (14)128.7
C3—H3B···F2iii0.992.553.307 (3)133.2
C8—H8B···F04iii0.992.523.493 (3)166.5
C4—H4A···F6iv0.992.433.205 (4)134.4
C5—H5···F5Civ12.162.798 (15)120.2
C6—H6···F05iv12.543.481 (3)155.8
C7—H7A···F3v0.992.563.348 (3)136.3
C10—H10···F01vi0.952.353.289 (3)168.4
C10—H10···F30.952.342.711 (3)102.8
Symmetry codes: (i) x+1, y, z; (ii) x, y+1/2, z1/2; (iii) x, y1/2, z+1/2; (iv) x, y, z+1; (v) x, y1, z; (vi) x, y+1, z+1.
 

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