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
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).
(8Fth3) (acetylacetonato)(
η4-
cyclo-octa-1,5-dienyl)palladium(II) hexafluorophosphate
top
Crystal data top
C13H19O2Pd·F6P | F(000) = 912 |
Mr = 458.65 | Dx = 1.917 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4688 reflections |
a = 9.3166 (6) Å | θ = 3.2–28.3° |
b = 15.4676 (8) Å | µ = 1.34 mm−1 |
c = 12.6132 (6) Å | T = 100 K |
β = 119.016 (4)° | Cuboid, colourless |
V = 1589.49 (15) Å3 | 0.13 × 0.07 × 0.03 mm |
Z = 4 | |
Data collection top
Bruker X8 Apex II 4K Kappa CCD diffractometer | 3952 independent reflections |
Radiation source: sealed tube | 3112 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 512 pixels mm-1 | θmax = 28.3°, θmin = 3.3° |
ϕ and ω scans | h = −12→12 |
Absorption correction: multi-scan SADABS (Bruker, 2004) | k = −13→20 |
Tmin = 0.846, Tmax = 0.961 | l = −16→16 |
10747 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-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 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.67 e Å−3 |
Crystal data top
C13H19O2Pd·F6P | V = 1589.49 (15) Å3 |
Mr = 458.65 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.3166 (6) Å | µ = 1.34 mm−1 |
b = 15.4676 (8) Å | T = 100 K |
c = 12.6132 (6) Å | 0.13 × 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 = 0.961 | Rint = 0.041 |
10747 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.70 e Å−3 |
3952 reflections | Δρmin = −0.67 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 1.1389 (4) | 0.08218 (19) | 0.1348 (3) | 0.0179 (7) | |
H1 | 1.1353 | 0.0237 | 0.0999 | 0.021* | |
C2 | 1.0027 (4) | 0.1320 (2) | 0.0658 (3) | 0.0182 (7) | |
H2 | 0.9192 | 0.1032 | −0.0103 | 0.022* | |
C3 | 0.9930 (4) | 0.22943 (19) | 0.0621 (3) | 0.0198 (7) | |
H3A | 0.877 | 0.2469 | 0.0299 | 0.024* | |
H3B | 1.0298 | 0.251 | 0.0052 | 0.024* | |
C4 | 1.0966 (4) | 0.27235 (19) | 0.1856 (3) | 0.0184 (7) | |
H4A | 1.2114 | 0.2771 | 0.2018 | 0.022* | |
H4B | 1.0549 | 0.3316 | 0.1833 | 0.022* | |
C5 | 1.0935 (4) | 0.22237 (17) | 0.2879 (3) | 0.0147 (6) | |
H5 | 1.0431 | 0.2547 | 0.3303 | 0.018* | |
C6 | 1.2094 (4) | 0.16217 (18) | 0.3596 (3) | 0.0152 (6) | |
H6 | 1.228 | 0.159 | 0.4445 | 0.018* | |
C7 | 1.3519 (4) | 0.1317 (2) | 0.3455 (3) | 0.0197 (7) | |
H7A | 1.3936 | 0.077 | 0.3911 | 0.024* | |
H7B | 1.441 | 0.175 | 0.3824 | 0.024* | |
C8 | 1.3114 (4) | 0.1167 (2) | 0.2134 (3) | 0.0202 (7) | |
H8A | 1.3236 | 0.1719 | 0.1789 | 0.024* | |
H8B | 1.3913 | 0.0751 | 0.212 | 0.024* | |
C9 | 0.7323 (4) | −0.03520 (18) | 0.1496 (3) | 0.0173 (7) | |
C10 | 0.7097 (4) | −0.01654 (18) | 0.2488 (3) | 0.0165 (6) | |
H10 | 0.6228 | −0.046 | 0.2526 | 0.02* | |
C11 | 0.8017 (4) | 0.04091 (17) | 0.3429 (3) | 0.0129 (6) | |
C12 | 0.6246 (4) | −0.10134 (19) | 0.0580 (3) | 0.0224 (7) | |
H12A | 0.5579 | −0.0732 | −0.0205 | 0.034* | |
H12B | 0.5525 | −0.128 | 0.0851 | 0.034* | |
H12C | 0.6933 | −0.146 | 0.0499 | 0.034* | |
C13 | 0.7626 (4) | 0.0515 (2) | 0.4446 (3) | 0.0190 (7) | |
H13A | 0.8611 | 0.0397 | 0.5221 | 0.029* | |
H13B | 0.6757 | 0.0108 | 0.4335 | 0.029* | |
H13C | 0.7255 | 0.1107 | 0.4447 | 0.029* | |
O1 | 0.8401 (3) | −0.00150 (12) | 0.12611 (18) | 0.0169 (5) | |
O2 | 0.9223 (3) | 0.08719 (12) | 0.35432 (18) | 0.0149 (4) | |
F1 | 0.5466 (3) | −0.19410 (13) | 0.35376 (18) | 0.0373 (5) | |
F2 | 0.3063 (3) | −0.25654 (13) | 0.2171 (2) | 0.0436 (6) | |
F3 | 0.1666 (3) | −0.14130 (13) | 0.22856 (19) | 0.0379 (5) | |
F4 | 0.4062 (3) | −0.08044 (11) | 0.3662 (2) | 0.0370 (6) | |
F5 | 0.3406 (3) | −0.21443 (13) | 0.39866 (17) | 0.0358 (5) | |
F6 | 0.3687 (3) | −0.12125 (15) | 0.18342 (18) | 0.0410 (6) | |
P1 | 0.35617 (11) | −0.16884 (5) | 0.29156 (7) | 0.01942 (19) | |
Pd1 | 0.99194 (3) | 0.092702 (13) | 0.22746 (2) | 0.01228 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0245 (19) | 0.0195 (15) | 0.0172 (16) | −0.0005 (13) | 0.0161 (14) | −0.0043 (12) |
C2 | 0.0247 (19) | 0.0226 (16) | 0.0128 (15) | −0.0029 (14) | 0.0133 (14) | −0.0019 (12) |
C3 | 0.0250 (19) | 0.0215 (16) | 0.0144 (15) | −0.0020 (14) | 0.0108 (14) | 0.0020 (12) |
C4 | 0.0215 (18) | 0.0142 (14) | 0.0232 (16) | −0.0021 (13) | 0.0137 (15) | −0.0009 (12) |
C5 | 0.0202 (18) | 0.0109 (13) | 0.0130 (14) | −0.0049 (12) | 0.0082 (13) | −0.0044 (11) |
C6 | 0.0161 (17) | 0.0171 (15) | 0.0122 (14) | −0.0035 (12) | 0.0068 (13) | −0.0046 (11) |
C7 | 0.0128 (17) | 0.0230 (16) | 0.0205 (16) | −0.0004 (13) | 0.0061 (14) | −0.0012 (13) |
C8 | 0.0166 (17) | 0.0207 (15) | 0.0275 (18) | −0.0004 (13) | 0.0140 (15) | −0.0043 (13) |
C9 | 0.0147 (17) | 0.0110 (14) | 0.0216 (16) | 0.0043 (12) | 0.0053 (14) | 0.0025 (12) |
C10 | 0.0132 (16) | 0.0145 (14) | 0.0228 (16) | −0.0016 (12) | 0.0095 (13) | 0.0037 (12) |
C11 | 0.0123 (16) | 0.0103 (13) | 0.0163 (15) | 0.0048 (11) | 0.0070 (13) | 0.0046 (11) |
C12 | 0.0245 (19) | 0.0189 (16) | 0.0240 (18) | −0.0016 (14) | 0.0120 (15) | −0.0031 (12) |
C13 | 0.0142 (17) | 0.0219 (16) | 0.0230 (17) | 0.0011 (13) | 0.0107 (14) | 0.0012 (13) |
O1 | 0.0154 (12) | 0.0173 (10) | 0.0186 (11) | −0.0052 (9) | 0.0087 (9) | −0.0051 (8) |
O2 | 0.0122 (11) | 0.0185 (10) | 0.0145 (11) | −0.0012 (9) | 0.0070 (9) | −0.0011 (8) |
F1 | 0.0207 (12) | 0.0448 (13) | 0.0398 (13) | 0.0027 (10) | 0.0096 (10) | −0.0068 (10) |
F2 | 0.0447 (16) | 0.0365 (12) | 0.0398 (13) | −0.0138 (11) | 0.0128 (12) | −0.0234 (10) |
F3 | 0.0200 (12) | 0.0431 (12) | 0.0484 (14) | −0.0005 (10) | 0.0149 (11) | 0.0140 (10) |
F4 | 0.0471 (16) | 0.0232 (10) | 0.0390 (13) | −0.0086 (10) | 0.0195 (12) | −0.0098 (9) |
F5 | 0.0434 (15) | 0.0392 (12) | 0.0261 (11) | −0.0107 (10) | 0.0180 (10) | 0.0073 (9) |
F6 | 0.0289 (13) | 0.0697 (15) | 0.0229 (11) | −0.0187 (12) | 0.0114 (10) | 0.0064 (10) |
P1 | 0.0177 (5) | 0.0216 (4) | 0.0181 (4) | −0.0064 (3) | 0.0079 (4) | −0.0034 (3) |
Pd1 | 0.01225 (13) | 0.01267 (12) | 0.01238 (13) | −0.00086 (9) | 0.00634 (10) | −0.00065 (8) |
Geometric parameters (Å, º) top
C1—C2 | 1.375 (5) | C8—H8B | 0.99 |
C1—C8 | 1.518 (5) | C9—O1 | 1.286 (4) |
C1—Pd1 | 2.196 (3) | C9—C10 | 1.397 (4) |
C1—H1 | 1 | C9—C12 | 1.504 (4) |
C2—C3 | 1.509 (4) | C10—C11 | 1.395 (4) |
C2—Pd1 | 2.176 (3) | C10—H10 | 0.95 |
C2—H2 | 1 | C11—O2 | 1.280 (3) |
C3—C4 | 1.530 (4) | C11—C13 | 1.503 (4) |
C3—H3A | 0.99 | C12—H12A | 0.98 |
C3—H3B | 0.99 | C12—H12B | 0.98 |
C4—C5 | 1.516 (4) | C12—H12C | 0.98 |
C4—H4A | 0.99 | C13—H13A | 0.98 |
C4—H4B | 0.99 | C13—H13B | 0.98 |
C5—C6 | 1.380 (4) | C13—H13C | 0.98 |
C5—Pd1 | 2.191 (3) | O1—Pd1 | 2.0012 (19) |
C5—H5 | 1 | O2—Pd1 | 1.999 (2) |
C6—C7 | 1.498 (4) | F1—P1 | 1.602 (2) |
C6—Pd1 | 2.182 (3) | F2—P1 | 1.586 (2) |
C6—H6 | 1 | F3—P1 | 1.604 (2) |
C7—C8 | 1.537 (4) | F4—P1 | 1.5962 (19) |
C7—H7A | 0.99 | F5—P1 | 1.591 (2) |
C7—H7B | 0.99 | F6—P1 | 1.603 (2) |
C8—H8A | 0.99 | | |
| | | |
C2—C1—C8 | 125.2 (3) | C11—C10—C9 | 126.6 (3) |
C2—C1—Pd1 | 70.90 (18) | C11—C10—H10 | 116.7 |
C8—C1—Pd1 | 111.2 (2) | C9—C10—H10 | 116.7 |
C2—C1—H1 | 113.9 | O2—C11—C10 | 126.5 (3) |
C8—C1—H1 | 113.9 | O2—C11—C13 | 114.0 (3) |
Pd1—C1—H1 | 113.9 | C10—C11—C13 | 119.5 (3) |
C1—C2—C3 | 127.0 (3) | C9—C12—H12A | 109.5 |
C1—C2—Pd1 | 72.44 (18) | C9—C12—H12B | 109.5 |
C3—C2—Pd1 | 106.18 (19) | H12A—C12—H12B | 109.5 |
C1—C2—H2 | 114.1 | C9—C12—H12C | 109.5 |
C3—C2—H2 | 114.1 | H12A—C12—H12C | 109.5 |
Pd1—C2—H2 | 114.1 | H12B—C12—H12C | 109.5 |
C2—C3—C4 | 113.8 (3) | C11—C13—H13A | 109.5 |
C2—C3—H3A | 108.8 | C11—C13—H13B | 109.5 |
C4—C3—H3A | 108.8 | H13A—C13—H13B | 109.5 |
C2—C3—H3B | 108.8 | C11—C13—H13C | 109.5 |
C4—C3—H3B | 108.8 | H13A—C13—H13C | 109.5 |
H3A—C3—H3B | 107.7 | H13B—C13—H13C | 109.5 |
C5—C4—C3 | 112.5 (2) | C9—O1—Pd1 | 122.48 (19) |
C5—C4—H4A | 109.1 | C11—O2—Pd1 | 122.82 (18) |
C3—C4—H4A | 109.1 | F2—P1—F5 | 90.13 (12) |
C5—C4—H4B | 109.1 | F2—P1—F4 | 179.88 (17) |
C3—C4—H4B | 109.1 | F5—P1—F4 | 89.97 (12) |
H4A—C4—H4B | 107.8 | F2—P1—F1 | 91.05 (12) |
C6—C5—C4 | 124.7 (3) | F5—P1—F1 | 90.65 (12) |
C6—C5—Pd1 | 71.26 (16) | F4—P1—F1 | 89.02 (12) |
C4—C5—Pd1 | 110.73 (18) | F2—P1—F6 | 90.61 (13) |
C6—C5—H5 | 114.1 | F5—P1—F6 | 178.64 (14) |
C4—C5—H5 | 114.1 | F4—P1—F6 | 89.30 (12) |
Pd1—C5—H5 | 114.1 | F1—P1—F6 | 90.47 (13) |
C5—C6—C7 | 126.3 (3) | F2—P1—F3 | 89.87 (13) |
C5—C6—Pd1 | 71.95 (17) | F5—P1—F3 | 90.37 (12) |
C7—C6—Pd1 | 107.63 (19) | F4—P1—F3 | 90.05 (12) |
C5—C6—H6 | 114.1 | F1—P1—F3 | 178.62 (12) |
C7—C6—H6 | 114.1 | F6—P1—F3 | 88.49 (12) |
Pd1—C6—H6 | 114.1 | O2—Pd1—O1 | 94.41 (8) |
C6—C7—C8 | 114.2 (3) | O2—Pd1—C2 | 160.46 (10) |
C6—C7—H7A | 108.7 | O1—Pd1—C2 | 86.82 (10) |
C8—C7—H7A | 108.7 | O2—Pd1—C6 | 87.21 (10) |
C6—C7—H7B | 108.7 | O1—Pd1—C6 | 162.43 (10) |
C8—C7—H7B | 108.7 | C2—Pd1—C6 | 97.49 (12) |
H7A—C7—H7B | 107.6 | O2—Pd1—C5 | 90.78 (10) |
C1—C8—C7 | 112.8 (3) | O1—Pd1—C5 | 160.23 (10) |
C1—C8—H8A | 109 | C2—Pd1—C5 | 82.06 (11) |
C7—C8—H8A | 109 | C6—Pd1—C5 | 36.79 (11) |
C1—C8—H8B | 109 | O2—Pd1—C1 | 162.06 (10) |
C7—C8—H8B | 109 | O1—Pd1—C1 | 92.08 (10) |
H8A—C8—H8B | 107.8 | C2—Pd1—C1 | 36.66 (12) |
O1—C9—C10 | 126.6 (3) | C6—Pd1—C1 | 81.67 (12) |
O1—C9—C12 | 113.8 (3) | C5—Pd1—C1 | 88.71 (11) |
C10—C9—C12 | 119.6 (3) | | |
| | | |
C8—C1—C2—C3 | −5.7 (5) | C3—C2—Pd1—O2 | 43.5 (4) |
Pd1—C1—C2—C3 | 97.3 (3) | C1—C2—Pd1—O1 | −97.80 (19) |
C8—C1—C2—Pd1 | −103.0 (3) | C3—C2—Pd1—O1 | 137.7 (2) |
C1—C2—C3—C4 | −37.9 (4) | C1—C2—Pd1—C6 | 65.08 (19) |
Pd1—C2—C3—C4 | 42.1 (3) | C3—C2—Pd1—C6 | −59.4 (2) |
C2—C3—C4—C5 | −38.2 (4) | C1—C2—Pd1—C5 | 98.6 (2) |
C3—C4—C5—C6 | 94.8 (4) | C3—C2—Pd1—C5 | −25.9 (2) |
C3—C4—C5—Pd1 | 13.7 (3) | C3—C2—Pd1—C1 | −124.5 (3) |
C4—C5—C6—C7 | −3.7 (5) | C5—C6—Pd1—O2 | −95.04 (18) |
Pd1—C5—C6—C7 | 99.0 (3) | C7—C6—Pd1—O2 | 141.6 (2) |
C4—C5—C6—Pd1 | −102.7 (3) | C5—C6—Pd1—O1 | 169.2 (3) |
C5—C6—C7—C8 | −41.2 (4) | C7—C6—Pd1—O1 | 45.8 (4) |
Pd1—C6—C7—C8 | 39.0 (3) | C5—C6—Pd1—C2 | 65.90 (19) |
C2—C1—C8—C7 | 93.4 (4) | C7—C6—Pd1—C2 | −57.4 (2) |
Pd1—C1—C8—C7 | 12.3 (3) | C7—C6—Pd1—C5 | −123.3 (3) |
C6—C7—C8—C1 | −35.0 (4) | C5—C6—Pd1—C1 | 99.08 (19) |
O1—C9—C10—C11 | −1.4 (5) | C7—C6—Pd1—C1 | −24.3 (2) |
C12—C9—C10—C11 | 178.0 (3) | C6—C5—Pd1—O2 | 84.29 (18) |
C9—C10—C11—O2 | 0.6 (5) | C4—C5—Pd1—O2 | −154.7 (2) |
C9—C10—C11—C13 | −178.5 (3) | C6—C5—Pd1—O1 | −170.3 (2) |
C10—C9—O1—Pd1 | −3.8 (4) | C4—C5—Pd1—O1 | −49.4 (4) |
C12—C9—O1—Pd1 | 176.70 (19) | C6—C5—Pd1—C2 | −114.0 (2) |
C10—C11—O2—Pd1 | 5.2 (4) | C4—C5—Pd1—C2 | 7.0 (2) |
C13—C11—O2—Pd1 | −175.62 (18) | C4—C5—Pd1—C6 | 121.0 (3) |
C11—O2—Pd1—O1 | −7.6 (2) | C6—C5—Pd1—C1 | −77.77 (19) |
C11—O2—Pd1—C2 | 85.3 (4) | C4—C5—Pd1—C1 | 43.2 (2) |
C11—O2—Pd1—C6 | −170.0 (2) | C2—C1—Pd1—O2 | −166.9 (3) |
C11—O2—Pd1—C5 | 153.3 (2) | C8—C1—Pd1—O2 | −45.6 (4) |
C11—O2—Pd1—C1 | −118.4 (3) | C2—C1—Pd1—O1 | 81.84 (19) |
C9—O1—Pd1—O2 | 6.9 (2) | C8—C1—Pd1—O1 | −156.8 (2) |
C9—O1—Pd1—C2 | −153.6 (2) | C8—C1—Pd1—C2 | 121.3 (3) |
C9—O1—Pd1—C6 | 101.6 (4) | C2—C1—Pd1—C6 | −114.66 (19) |
C9—O1—Pd1—C5 | −97.9 (3) | C8—C1—Pd1—C6 | 6.6 (2) |
C9—O1—Pd1—C1 | 170.1 (2) | C2—C1—Pd1—C5 | −78.40 (19) |
C1—C2—Pd1—O2 | 168.0 (2) | C8—C1—Pd1—C5 | 42.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···F6 | 0.95 | 2.39 | 3.295 (4) | 159 |
C7—H7A···F4i | 0.99 | 2.47 | 3.311 (4) | 143 |
C2—H2···F6ii | 1 | 2.52 | 3.366 (4) | 142 |
C2—H2···F3ii | 1 | 2.54 | 3.257 (4) | 129 |
C5—H5···F3iii | 1 | 2.36 | 3.142 (4) | 135 |
C8—H8A···F1iv | 0.99 | 2.53 | 3.481 (4) | 161 |
C6—H6···F1v | 1 | 2.45 | 3.242 (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·BF4 | F(000) = 800 |
Mr = 400.49 | Dx = 1.815 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 8277 reflections |
a = 26.2908 (11) Å | θ = 2.8–28.4° |
b = 7.1684 (3) Å | µ = 1.31 mm−1 |
c = 7.7782 (3) Å | T = 100 K |
V = 1465.90 (10) Å3 | Needle, yellow |
Z = 4 | 0.34 × 0.1 × 0.07 mm |
Data collection top
Bruker X8 APEX-II 4K Kappa CCD diffractometer | 3117 independent reflections |
Radiation source: sealed tube | 2960 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 512 pixels mm-1 | θmax = 28.4°, θmin = 3.0° |
ϕ and ω scans | h = −35→35 |
Absorption correction: multi-scan SADABS (Bruker, 2004) | k = −9→9 |
Tmin = 0.664, Tmax = 0.914 | l = −10→6 |
15654 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.022 | H-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 reflections | Δρmax = 1.05 e Å−3 |
192 parameters | Δρmin = −0.61 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881, 1143 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (3) |
Crystal data top
C13H19O2Pd·BF4 | V = 1465.90 (10) Å3 |
Mr = 400.49 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 26.2908 (11) Å | µ = 1.31 mm−1 |
b = 7.1684 (3) Å | T = 100 K |
c = 7.7782 (3) Å | 0.34 × 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 = 0.914 | Rint = 0.025 |
15654 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.022 | H-atom parameters constrained |
wR(F2) = 0.062 | Δρmax = 1.05 e Å−3 |
S = 0.93 | Δρmin = −0.61 e Å−3 |
3117 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881, 1143 Friedel pairs |
192 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.60809 (9) | 0.5373 (3) | 0.1035 (6) | 0.0196 (6) | |
H1 | 0.6335 | 0.435 | 0.0868 | 0.024* | |
C2 | 0.60891 (10) | 0.6160 (4) | 0.2663 (4) | 0.0201 (6) | |
H2 | 0.6345 | 0.559 | 0.3458 | 0.024* | |
C3 | 0.56498 (16) | 0.7094 (5) | 0.3562 (5) | 0.0236 (8) | |
H3A | 0.5785 | 0.7887 | 0.4498 | 0.028* | |
H3B | 0.5433 | 0.6122 | 0.4093 | 0.028* | |
C4 | 0.53191 (12) | 0.8302 (4) | 0.2372 (4) | 0.0234 (7) | |
H4A | 0.5067 | 0.7497 | 0.1785 | 0.028* | |
H4B | 0.513 | 0.9221 | 0.3074 | 0.028* | |
C5 | 0.56289 (9) | 0.9322 (4) | 0.1042 (5) | 0.0201 (6) | |
H5 | 0.5614 | 1.0711 | 0.1145 | 0.024* | |
C6 | 0.57207 (10) | 0.8689 (5) | −0.0620 (4) | 0.0217 (6) | |
H6 | 0.5755 | 0.9706 | −0.1492 | 0.026* | |
C7 | 0.55728 (17) | 0.6837 (5) | −0.1361 (5) | 0.0262 (9) | |
H7A | 0.5793 | 0.6574 | −0.2365 | 0.031* | |
H7B | 0.5218 | 0.6916 | −0.1778 | 0.031* | |
C8 | 0.56142 (12) | 0.5199 (5) | −0.0089 (4) | 0.0262 (7) | |
H8A | 0.5307 | 0.5167 | 0.0646 | 0.031* | |
H8B | 0.563 | 0.4012 | −0.0737 | 0.031* | |
C9 | 0.75094 (10) | 0.8105 (3) | 0.1099 (4) | 0.0137 (6) | |
C10 | 0.75462 (11) | 0.9832 (4) | 0.0294 (4) | 0.0157 (5) | |
H10 | 0.7879 | 1.0286 | 0.0071 | 0.019* | |
C11 | 0.71414 (10) | 1.0961 (4) | −0.0217 (4) | 0.0159 (5) | |
C12 | 0.79890 (10) | 0.7101 (4) | 0.1601 (4) | 0.0184 (6) | |
H12A | 0.7969 | 0.6732 | 0.2812 | 0.028* | |
H12B | 0.8281 | 0.7929 | 0.1435 | 0.028* | |
H12C | 0.8029 | 0.5987 | 0.0884 | 0.028* | |
C13 | 0.72542 (12) | 1.2841 (4) | −0.1019 (4) | 0.0199 (6) | |
H13A | 0.702 | 1.306 | −0.1978 | 0.03* | |
H13B | 0.7605 | 1.2856 | −0.1443 | 0.03* | |
H13C | 0.721 | 1.3822 | −0.0155 | 0.03* | |
B01 | 0.39222 (13) | 0.7791 (5) | 0.0047 (5) | 0.0218 (7) | |
O1 | 0.70986 (7) | 0.7205 (3) | 0.1445 (3) | 0.0166 (4) | |
O2 | 0.66675 (7) | 1.0606 (3) | −0.0062 (3) | 0.0178 (4) | |
F01 | 0.43805 (8) | 0.7577 (3) | −0.0801 (4) | 0.0446 (5) | |
F02 | 0.38406 (12) | 0.6316 (3) | 0.1112 (4) | 0.0598 (8) | |
F03 | 0.35462 (9) | 0.7848 (5) | −0.1197 (5) | 0.0629 (10) | |
F04 | 0.39108 (7) | 0.9455 (2) | 0.0947 (4) | 0.0378 (4) | |
Pd1 | 0.640693 (6) | 0.81950 (2) | 0.08800 (5) | 0.01336 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0161 (11) | 0.0167 (10) | 0.0260 (18) | −0.0022 (8) | −0.0013 (14) | 0.0066 (15) |
C2 | 0.0169 (13) | 0.0212 (13) | 0.0222 (15) | −0.0027 (11) | 0.0008 (11) | 0.0090 (12) |
C3 | 0.0234 (19) | 0.0301 (17) | 0.0173 (17) | −0.0031 (14) | 0.0061 (14) | 0.0026 (13) |
C4 | 0.0176 (14) | 0.0299 (16) | 0.0227 (16) | 0.0030 (11) | 0.0057 (12) | 0.0038 (12) |
C5 | 0.0128 (10) | 0.0231 (12) | 0.0244 (16) | 0.0061 (9) | −0.0005 (14) | 0.0017 (15) |
C6 | 0.0117 (12) | 0.0312 (15) | 0.0222 (15) | 0.0036 (11) | −0.0032 (11) | 0.0091 (13) |
C7 | 0.0186 (17) | 0.042 (2) | 0.0176 (18) | −0.0042 (13) | −0.0015 (14) | −0.0009 (13) |
C8 | 0.0214 (14) | 0.0308 (16) | 0.0265 (16) | −0.0070 (12) | −0.0027 (13) | −0.0040 (13) |
C9 | 0.0146 (11) | 0.0155 (10) | 0.0109 (19) | 0.0001 (8) | −0.0001 (11) | −0.0012 (10) |
C10 | 0.0141 (12) | 0.0152 (11) | 0.0178 (11) | −0.0028 (10) | 0.0012 (9) | 0.0007 (10) |
C11 | 0.0203 (12) | 0.0144 (12) | 0.0130 (12) | −0.0026 (10) | −0.0002 (11) | 0.0010 (10) |
C12 | 0.0123 (12) | 0.0181 (12) | 0.0249 (15) | 0.0012 (10) | 0.0014 (11) | 0.0045 (11) |
C13 | 0.0223 (15) | 0.0124 (11) | 0.0249 (15) | −0.0006 (10) | 0.0041 (12) | 0.0048 (11) |
B01 | 0.0210 (16) | 0.0197 (15) | 0.0246 (18) | −0.0001 (12) | −0.0007 (13) | −0.0032 (14) |
O1 | 0.0120 (8) | 0.0151 (8) | 0.0226 (10) | 0.0001 (7) | −0.0009 (7) | 0.0043 (7) |
O2 | 0.0172 (9) | 0.0156 (9) | 0.0207 (10) | 0.0009 (7) | 0.0005 (8) | 0.0044 (8) |
F01 | 0.0289 (11) | 0.0441 (12) | 0.0606 (16) | −0.0020 (10) | 0.0140 (11) | −0.0057 (12) |
F02 | 0.0979 (19) | 0.0327 (10) | 0.0488 (19) | 0.0024 (12) | 0.0334 (17) | 0.0115 (14) |
F03 | 0.0341 (14) | 0.086 (2) | 0.069 (2) | 0.0305 (12) | −0.0226 (12) | −0.0440 (18) |
F04 | 0.0533 (11) | 0.0263 (8) | 0.0338 (10) | −0.0028 (7) | −0.0022 (15) | −0.0121 (14) |
Pd1 | 0.01080 (9) | 0.01499 (9) | 0.01429 (10) | −0.00024 (5) | 0.00009 (12) | 0.00345 (11) |
Geometric parameters (Å, º) top
C1—C2 | 1.387 (6) | C8—H8A | 0.99 |
C1—C8 | 1.511 (4) | C8—H8B | 0.99 |
C1—Pd1 | 2.200 (2) | C9—O1 | 1.287 (3) |
C1—H1 | 1 | C9—C10 | 1.390 (3) |
C2—C3 | 1.507 (5) | C9—C12 | 1.504 (4) |
C2—Pd1 | 2.180 (3) | C10—C11 | 1.395 (4) |
C2—H2 | 1 | C10—H10 | 0.95 |
C3—C4 | 1.537 (5) | C11—O2 | 1.277 (3) |
C3—H3A | 0.99 | C11—C13 | 1.514 (4) |
C3—H3B | 0.99 | C12—H12A | 0.98 |
C4—C5 | 1.506 (5) | C12—H12B | 0.98 |
C4—H4A | 0.99 | C12—H12C | 0.98 |
C4—H4B | 0.99 | C13—H13A | 0.98 |
C5—C6 | 1.391 (5) | C13—H13B | 0.98 |
C5—Pd1 | 2.203 (2) | C13—H13C | 0.98 |
C5—H5 | 1 | B01—F02 | 1.360 (5) |
C6—C7 | 1.498 (5) | B01—F01 | 1.382 (4) |
C6—Pd1 | 2.177 (3) | B01—F04 | 1.383 (4) |
C6—H6 | 1 | B01—F03 | 1.384 (4) |
C7—C8 | 1.540 (5) | O1—Pd1 | 2.0011 (19) |
C7—H7A | 0.99 | O2—Pd1 | 1.9980 (18) |
C7—H7B | 0.99 | | |
| | | |
C2—C1—C8 | 125.0 (3) | C7—C8—H8B | 109.3 |
C2—C1—Pd1 | 70.73 (15) | H8A—C8—H8B | 108 |
C8—C1—Pd1 | 111.1 (2) | O1—C9—C10 | 126.8 (2) |
C2—C1—H1 | 114 | O1—C9—C12 | 114.1 (2) |
C8—C1—H1 | 114 | C10—C9—C12 | 119.0 (2) |
Pd1—C1—H1 | 114 | C9—C10—C11 | 126.3 (3) |
C1—C2—C3 | 126.3 (3) | C9—C10—H10 | 116.8 |
C1—C2—Pd1 | 72.36 (17) | C11—C10—H10 | 116.8 |
C3—C2—Pd1 | 107.0 (2) | O2—C11—C10 | 127.0 (2) |
C1—C2—H2 | 114.2 | O2—C11—C13 | 114.1 (2) |
C3—C2—H2 | 114.2 | C10—C11—C13 | 119.0 (2) |
Pd1—C2—H2 | 114.2 | C9—C12—H12A | 109.5 |
C2—C3—C4 | 113.9 (3) | C9—C12—H12B | 109.5 |
C2—C3—H3A | 108.8 | H12A—C12—H12B | 109.5 |
C4—C3—H3A | 108.8 | C9—C12—H12C | 109.5 |
C2—C3—H3B | 108.8 | H12A—C12—H12C | 109.5 |
C4—C3—H3B | 108.8 | H12B—C12—H12C | 109.5 |
H3A—C3—H3B | 107.7 | C11—C13—H13A | 109.5 |
C5—C4—C3 | 112.4 (3) | C11—C13—H13B | 109.5 |
C5—C4—H4A | 109.1 | H13A—C13—H13B | 109.5 |
C3—C4—H4A | 109.1 | C11—C13—H13C | 109.5 |
C5—C4—H4B | 109.1 | H13A—C13—H13C | 109.5 |
C3—C4—H4B | 109.1 | H13B—C13—H13C | 109.5 |
H4A—C4—H4B | 107.9 | F02—B01—F01 | 110.0 (3) |
C6—C5—C4 | 125.0 (3) | F02—B01—F04 | 111.1 (3) |
C6—C5—Pd1 | 70.49 (15) | F01—B01—F04 | 110.8 (3) |
C4—C5—Pd1 | 111.30 (19) | F02—B01—F03 | 109.6 (3) |
C6—C5—H5 | 114 | F01—B01—F03 | 107.0 (3) |
C4—C5—H5 | 114 | F04—B01—F03 | 108.2 (3) |
Pd1—C5—H5 | 114 | C9—O1—Pd1 | 122.60 (16) |
C5—C6—C7 | 127.0 (3) | C11—O2—Pd1 | 122.80 (17) |
C5—C6—Pd1 | 72.48 (16) | O2—Pd1—O1 | 94.35 (8) |
C7—C6—Pd1 | 106.1 (2) | O2—Pd1—C6 | 86.97 (10) |
C5—C6—H6 | 114.1 | O1—Pd1—C6 | 158.19 (11) |
C7—C6—H6 | 114.1 | O2—Pd1—C2 | 160.69 (10) |
Pd1—C6—H6 | 114.1 | O1—Pd1—C2 | 88.35 (9) |
C6—C7—C8 | 114.2 (3) | C6—Pd1—C2 | 97.58 (11) |
C6—C7—H7A | 108.7 | O2—Pd1—C1 | 161.58 (14) |
C8—C7—H7A | 108.7 | O1—Pd1—C1 | 90.91 (9) |
C6—C7—H7B | 108.7 | C6—Pd1—C1 | 81.72 (12) |
C8—C7—H7B | 108.7 | C2—Pd1—C1 | 36.91 (15) |
H7A—C7—H7B | 107.6 | O2—Pd1—C5 | 91.27 (9) |
C1—C8—C7 | 111.5 (3) | O1—Pd1—C5 | 164.02 (13) |
C1—C8—H8A | 109.3 | C6—Pd1—C5 | 37.02 (13) |
C7—C8—H8A | 109.3 | C2—Pd1—C5 | 81.56 (11) |
C1—C8—H8B | 109.3 | C1—Pd1—C5 | 88.42 (9) |
| | | |
C8—C1—C2—C3 | −4.4 (5) | C7—C6—Pd1—O2 | 139.4 (2) |
Pd1—C1—C2—C3 | 98.4 (3) | C5—C6—Pd1—O1 | 169.7 (2) |
C8—C1—C2—Pd1 | −102.8 (3) | C7—C6—Pd1—O1 | 45.3 (4) |
C1—C2—C3—C4 | −39.4 (4) | C5—C6—Pd1—C2 | 65.00 (19) |
Pd1—C2—C3—C4 | 40.9 (3) | C7—C6—Pd1—C2 | −59.4 (2) |
C2—C3—C4—C5 | −37.4 (4) | C5—C6—Pd1—C1 | 98.4 (2) |
C3—C4—C5—C6 | 94.4 (4) | C7—C6—Pd1—C1 | −26.0 (2) |
C3—C4—C5—Pd1 | 13.9 (4) | C7—C6—Pd1—C5 | −124.5 (3) |
C4—C5—C6—C7 | −5.6 (5) | C1—C2—Pd1—O2 | 167.8 (2) |
Pd1—C5—C6—C7 | 97.2 (3) | C3—C2—Pd1—O2 | 44.2 (4) |
C4—C5—C6—Pd1 | −102.9 (3) | C1—C2—Pd1—O1 | −93.72 (16) |
C5—C6—C7—C8 | −36.9 (5) | C3—C2—Pd1—O1 | 142.7 (2) |
Pd1—C6—C7—C8 | 43.0 (3) | C1—C2—Pd1—C6 | 65.21 (17) |
C2—C1—C8—C7 | 95.1 (4) | C3—C2—Pd1—C6 | −58.4 (2) |
Pd1—C1—C8—C7 | 14.4 (3) | C3—C2—Pd1—C1 | −123.6 (3) |
C6—C7—C8—C1 | −39.4 (4) | C1—C2—Pd1—C5 | 98.69 (18) |
O1—C9—C10—C11 | 3.3 (5) | C3—C2—Pd1—C5 | −24.9 (2) |
C12—C9—C10—C11 | −178.4 (3) | C2—C1—Pd1—O2 | −167.3 (2) |
C9—C10—C11—O2 | −1.1 (5) | C8—C1—Pd1—O2 | −46.1 (4) |
C9—C10—C11—C13 | 177.7 (3) | C2—C1—Pd1—O1 | 86.03 (16) |
C10—C9—O1—Pd1 | −0.7 (4) | C8—C1—Pd1—O1 | −152.8 (2) |
C12—C9—O1—Pd1 | −178.97 (19) | C2—C1—Pd1—C6 | −114.58 (17) |
C10—C11—O2—Pd1 | −3.3 (4) | C8—C1—Pd1—C6 | 6.6 (2) |
C13—C11—O2—Pd1 | 177.89 (19) | C8—C1—Pd1—C2 | 121.1 (3) |
C11—O2—Pd1—O1 | 4.3 (2) | C2—C1—Pd1—C5 | −78.01 (19) |
C11—O2—Pd1—C6 | −153.9 (2) | C8—C1—Pd1—C5 | 43.1 (3) |
C11—O2—Pd1—C2 | 101.7 (3) | C6—C5—Pd1—O2 | 83.27 (18) |
C11—O2—Pd1—C1 | −101.9 (3) | C4—C5—Pd1—O2 | −155.7 (2) |
C11—O2—Pd1—C5 | 169.3 (2) | C6—C5—Pd1—O1 | −166.1 (3) |
C9—O1—Pd1—O2 | −2.4 (2) | C4—C5—Pd1—O1 | −45.1 (4) |
C9—O1—Pd1—C6 | 90.3 (3) | C4—C5—Pd1—C6 | 121.0 (3) |
C9—O1—Pd1—C2 | −163.3 (2) | C6—C5—Pd1—C2 | −114.74 (19) |
C9—O1—Pd1—C1 | 159.9 (3) | C4—C5—Pd1—C2 | 6.3 (2) |
C9—O1—Pd1—C5 | −112.7 (3) | C6—C5—Pd1—C1 | −78.3 (2) |
C5—C6—Pd1—O2 | −96.14 (17) | C4—C5—Pd1—C1 | 42.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···F01 | 0.99 | 2.38 | 3.209 (5) | 141 |
C2—H2···F02i | 1 | 2.52 | 3.222 (4) | 127 |
C6—H6···F04ii | 1 | 2.26 | 3.137 (4) | 146 |
C12—H12B···F04iii | 0.98 | 2.53 | 3.497 (3) | 169 |
C10—H10···F03iii | 0.95 | 2.42 | 3.320 (4) | 159 |
C13—H13B···F03iii | 0.98 | 2.53 | 3.435 (4) | 153 |
Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+1, −y+2, z−1/2; (iii) x+1/2, −y+2, z. |
(9Tth12_L) (thenoyltrifluoroacetonato)(
η4-
cyclo-octa-1,5-dienyl)palladium(II) hexafluorophosphate
top
Crystal data top
C16H16F3O2PdS·F6P | F(000) = 1144 |
Mr = 580.72 | Dx = 2.019 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10209 reflections |
a = 9.9691 (2) Å | θ = 2.2–33.0° |
b = 17.0294 (3) Å | µ = 1.26 mm−1 |
c = 13.6427 (3) Å | T = 100 K |
β = 124.439 (1)° | Needle, orange |
V = 1910.15 (7) Å3 | 0.35 × 0.2 × 0.1 mm |
Z = 4 | |
Data collection top
CCD area detector diffractometer | 4606 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3596 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 16.1829 pixels mm-1 | θmax = 28°, θmin = 2.2° |
ω scans | h = −11→13 |
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 = −22→21 |
Tmin = 0.667, Tmax = 0.884 | l = −18→18 |
15058 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.061 | H-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 parameters | Δρmax = 1.15 e Å−3 |
0 restraints | Δρmin = −0.71 e Å−3 |
Crystal data top
C16H16F3O2PdS·F6P | V = 1910.15 (7) Å3 |
Mr = 580.72 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.9691 (2) Å | µ = 1.26 mm−1 |
b = 17.0294 (3) Å | T = 100 K |
c = 13.6427 (3) Å | 0.35 × 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 = 0.884 | Rint = 0.024 |
15058 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 1.01 | Δρmax = 1.15 e Å−3 |
4606 reflections | Δρmin = −0.71 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.6044 (2) | 0.77640 (12) | 0.32910 (19) | 0.0159 (5) | |
H1 | 0.5591 | 0.7466 | 0.3674 | 0.019* | |
C2 | 0.7142 (2) | 0.83430 (13) | 0.40058 (18) | 0.0146 (4) | |
H2 | 0.7346 | 0.8383 | 0.4811 | 0.018* | |
C3 | 0.8494 (3) | 0.86689 (13) | 0.39366 (19) | 0.0157 (5) | |
H3A | 0.9449 | 0.8317 | 0.4382 | 0.019* | |
H3B | 0.8816 | 0.9188 | 0.4332 | 0.019* | |
C4 | 0.8043 (3) | 0.87610 (13) | 0.26658 (19) | 0.0153 (5) | |
H4A | 0.8788 | 0.9146 | 0.2665 | 0.018* | |
H4B | 0.8193 | 0.8251 | 0.2391 | 0.018* | |
C5 | 0.6300 (3) | 0.90340 (12) | 0.18068 (18) | 0.0146 (4) | |
H5 | 0.6196 | 0.9561 | 0.1445 | 0.018* | |
C6 | 0.4995 (3) | 0.85390 (13) | 0.11038 (19) | 0.0159 (5) | |
H6 | 0.412 | 0.8772 | 0.0324 | 0.019* | |
C7 | 0.5031 (3) | 0.76561 (13) | 0.11138 (19) | 0.0186 (5) | |
H7A | 0.5443 | 0.7475 | 0.064 | 0.022* | |
H7B | 0.3906 | 0.7458 | 0.0722 | 0.022* | |
C8 | 0.6095 (3) | 0.72948 (13) | 0.23681 (19) | 0.0173 (5) | |
H8A | 0.5718 | 0.6753 | 0.2345 | 0.021* | |
H8B | 0.7234 | 0.7264 | 0.2606 | 0.021* | |
C9 | 0.3081 (2) | 0.94303 (12) | 0.35370 (18) | 0.0144 (4) | |
C10 | 0.2211 (2) | 0.99750 (13) | 0.26569 (19) | 0.0153 (4) | |
H10 | 0.1417 | 1.0273 | 0.2673 | 0.018* | |
C11 | 0.2410 (2) | 1.01279 (12) | 0.17182 (18) | 0.0131 (4) | |
C12 | 0.2724 (3) | 0.93220 (13) | 0.44707 (19) | 0.0162 (5) | |
C13 | 0.1421 (2) | 1.07354 (13) | 0.08575 (18) | 0.0141 (4) | |
C14 | 0.0167 (3) | 1.11729 (13) | 0.0749 (2) | 0.0165 (5) | |
H14 | −0.0194 | 1.1119 | 0.1258 | 0.02* | |
C15 | −0.0504 (3) | 1.17048 (13) | −0.0206 (2) | 0.0193 (5) | |
H15 | −0.1372 | 1.2053 | −0.0414 | 0.023* | |
C16 | 0.0227 (3) | 1.16667 (13) | −0.0801 (2) | 0.0197 (5) | |
H16 | −0.0077 | 1.1985 | −0.1468 | 0.024* | |
O1 | 0.42120 (18) | 0.89573 (9) | 0.37168 (13) | 0.0161 (3) | |
O2 | 0.33981 (17) | 0.97770 (8) | 0.15617 (12) | 0.0147 (3) | |
F01 | 1.19634 (16) | 0.93650 (8) | 0.82933 (12) | 0.0242 (3) | |
F1 | 0.20070 (16) | 0.86271 (8) | 0.43288 (12) | 0.0220 (3) | |
F02 | 1.02561 (16) | 0.85710 (8) | 0.67375 (12) | 0.0265 (3) | |
F2 | 0.17346 (16) | 0.98719 (8) | 0.44228 (12) | 0.0255 (3) | |
F3 | 0.40880 (15) | 0.93317 (8) | 0.55688 (11) | 0.0245 (3) | |
F03 | 1.24051 (17) | 0.80897 (8) | 0.67702 (12) | 0.0310 (3) | |
F04 | 1.40992 (16) | 0.88795 (8) | 0.83312 (13) | 0.0314 (4) | |
F05 | 1.19481 (17) | 0.93988 (8) | 0.66336 (12) | 0.0290 (3) | |
F06 | 1.23862 (18) | 0.80502 (8) | 0.84223 (12) | 0.0341 (4) | |
P01 | 1.21785 (7) | 0.87267 (3) | 0.75263 (5) | 0.01576 (13) | |
S1 | 0.17453 (7) | 1.09853 (3) | −0.02174 (5) | 0.01822 (12) | |
Pd1 | 0.491474 (19) | 0.891091 (10) | 0.260022 (14) | 0.01196 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0164 (11) | 0.0137 (11) | 0.0176 (11) | 0.0052 (8) | 0.0096 (9) | 0.0095 (9) |
C2 | 0.0131 (10) | 0.0158 (11) | 0.0109 (10) | 0.0037 (8) | 0.0044 (9) | 0.0051 (8) |
C3 | 0.0120 (10) | 0.0193 (11) | 0.0121 (10) | 0.0002 (8) | 0.0046 (9) | 0.0008 (8) |
C4 | 0.0124 (10) | 0.0185 (12) | 0.0152 (11) | −0.0011 (8) | 0.0079 (9) | 0.0009 (8) |
C5 | 0.0172 (11) | 0.0177 (12) | 0.0113 (10) | 0.0023 (8) | 0.0095 (9) | 0.0033 (8) |
C6 | 0.0163 (11) | 0.0194 (12) | 0.0112 (10) | 0.0020 (9) | 0.0074 (9) | 0.0012 (8) |
C7 | 0.0189 (11) | 0.0168 (12) | 0.0167 (11) | 0.0005 (9) | 0.0081 (10) | −0.0034 (9) |
C8 | 0.0155 (11) | 0.0137 (11) | 0.0212 (12) | 0.0004 (8) | 0.0095 (10) | 0.0016 (9) |
C9 | 0.0119 (10) | 0.0145 (11) | 0.0143 (11) | −0.0035 (8) | 0.0059 (9) | −0.0021 (8) |
C10 | 0.0139 (11) | 0.0150 (11) | 0.0171 (11) | −0.0001 (8) | 0.0089 (9) | −0.0010 (9) |
C11 | 0.0113 (10) | 0.0113 (10) | 0.0136 (10) | −0.0036 (8) | 0.0052 (9) | −0.0033 (8) |
C12 | 0.0144 (11) | 0.0165 (11) | 0.0169 (11) | 0.0006 (9) | 0.0085 (9) | 0.0010 (9) |
C13 | 0.0135 (10) | 0.0132 (11) | 0.0143 (11) | −0.0008 (8) | 0.0071 (9) | −0.0018 (8) |
C14 | 0.0150 (11) | 0.0167 (11) | 0.0190 (11) | −0.0002 (9) | 0.0104 (10) | 0.0007 (9) |
C15 | 0.0148 (11) | 0.0146 (11) | 0.0250 (12) | 0.0023 (9) | 0.0091 (10) | 0.0025 (9) |
C16 | 0.0193 (11) | 0.0145 (11) | 0.0191 (11) | 0.0023 (9) | 0.0071 (10) | 0.0058 (9) |
O1 | 0.0172 (8) | 0.0182 (8) | 0.0161 (8) | 0.0037 (6) | 0.0113 (7) | 0.0038 (6) |
O2 | 0.0141 (7) | 0.0157 (8) | 0.0133 (8) | 0.0029 (6) | 0.0071 (6) | 0.0025 (6) |
F01 | 0.0352 (8) | 0.0211 (7) | 0.0279 (7) | −0.0045 (6) | 0.0247 (7) | −0.0080 (6) |
F1 | 0.0215 (7) | 0.0232 (7) | 0.0250 (7) | −0.0026 (5) | 0.0153 (6) | 0.0043 (6) |
F02 | 0.0178 (7) | 0.0320 (8) | 0.0237 (8) | −0.0021 (6) | 0.0081 (6) | −0.0021 (6) |
F2 | 0.0335 (8) | 0.0267 (8) | 0.0263 (8) | 0.0127 (6) | 0.0230 (7) | 0.0069 (6) |
F3 | 0.0191 (7) | 0.0370 (8) | 0.0142 (7) | −0.0023 (6) | 0.0075 (6) | 0.0004 (6) |
F03 | 0.0303 (8) | 0.0305 (8) | 0.0322 (8) | −0.0036 (6) | 0.0177 (7) | −0.0173 (6) |
F04 | 0.0157 (7) | 0.0335 (8) | 0.0351 (9) | −0.0037 (6) | 0.0085 (7) | −0.0152 (7) |
F05 | 0.0431 (9) | 0.0259 (8) | 0.0241 (8) | −0.0032 (7) | 0.0227 (7) | 0.0025 (6) |
F06 | 0.0466 (9) | 0.0201 (8) | 0.0202 (7) | −0.0043 (6) | 0.0095 (7) | 0.0055 (6) |
P01 | 0.0157 (3) | 0.0164 (3) | 0.0129 (3) | −0.0001 (2) | 0.0068 (2) | −0.0024 (2) |
S1 | 0.0198 (3) | 0.0199 (3) | 0.0161 (3) | 0.0051 (2) | 0.0109 (2) | 0.0048 (2) |
Pd1 | 0.01125 (9) | 0.01228 (9) | 0.01165 (9) | 0.00155 (6) | 0.00606 (7) | 0.00168 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.384 (3) | C9—C10 | 1.370 (3) |
C1—C8 | 1.516 (3) | C9—C12 | 1.515 (3) |
C1—Pd1 | 2.184 (2) | C10—C11 | 1.427 (3) |
C1—H1 | 1 | C10—H10 | 0.95 |
C2—C3 | 1.509 (3) | C11—O2 | 1.269 (2) |
C2—Pd1 | 2.174 (2) | C11—C13 | 1.453 (3) |
C2—H2 | 1 | C12—F2 | 1.335 (2) |
C3—C4 | 1.533 (3) | C12—F3 | 1.338 (2) |
C3—H3A | 0.99 | C12—F1 | 1.339 (2) |
C3—H3B | 0.99 | C13—C14 | 1.390 (3) |
C4—C5 | 1.519 (3) | C13—S1 | 1.724 (2) |
C4—H4A | 0.99 | C14—C15 | 1.407 (3) |
C4—H4B | 0.99 | C14—H14 | 0.95 |
C5—C6 | 1.383 (3) | C15—C16 | 1.365 (3) |
C5—Pd1 | 2.194 (2) | C15—H15 | 0.95 |
C5—H5 | 1 | C16—S1 | 1.705 (2) |
C6—C7 | 1.504 (3) | C16—H16 | 0.95 |
C6—Pd1 | 2.182 (2) | O1—Pd1 | 2.0061 (15) |
C6—H6 | 1 | O2—Pd1 | 2.0114 (14) |
C7—C8 | 1.542 (3) | F01—P01 | 1.6051 (14) |
C7—H7A | 0.99 | F02—P01 | 1.6027 (14) |
C7—H7B | 0.99 | F03—P01 | 1.5984 (14) |
C8—H8A | 0.99 | F04—P01 | 1.6006 (14) |
C8—H8B | 0.99 | F05—P01 | 1.5905 (14) |
C9—O1 | 1.292 (2) | F06—P01 | 1.6055 (14) |
| | | |
C2—C1—C8 | 125.2 (2) | O2—C11—C10 | 125.48 (19) |
C2—C1—Pd1 | 71.11 (12) | O2—C11—C13 | 115.83 (19) |
C8—C1—Pd1 | 111.36 (14) | C10—C11—C13 | 118.69 (19) |
C2—C1—H1 | 113.8 | F2—C12—F3 | 107.53 (18) |
C8—C1—H1 | 113.8 | F2—C12—F1 | 107.07 (17) |
Pd1—C1—H1 | 113.8 | F3—C12—F1 | 107.12 (17) |
C1—C2—C3 | 126.7 (2) | F2—C12—C9 | 113.06 (18) |
C1—C2—Pd1 | 71.87 (12) | F3—C12—C9 | 111.53 (17) |
C3—C2—Pd1 | 106.50 (13) | F1—C12—C9 | 110.24 (18) |
C1—C2—H2 | 114.2 | C14—C13—C11 | 128.8 (2) |
C3—C2—H2 | 114.2 | C14—C13—S1 | 111.55 (16) |
Pd1—C2—H2 | 114.2 | C11—C13—S1 | 119.70 (16) |
C2—C3—C4 | 114.04 (18) | C13—C14—C15 | 111.8 (2) |
C2—C3—H3A | 108.7 | C13—C14—H14 | 124.1 |
C4—C3—H3A | 108.7 | C15—C14—H14 | 124.1 |
C2—C3—H3B | 108.7 | C16—C15—C14 | 112.7 (2) |
C4—C3—H3B | 108.7 | C16—C15—H15 | 123.7 |
H3A—C3—H3B | 107.6 | C14—C15—H15 | 123.7 |
C5—C4—C3 | 112.30 (18) | C15—C16—S1 | 112.71 (17) |
C5—C4—H4A | 109.1 | C15—C16—H16 | 123.6 |
C3—C4—H4A | 109.1 | S1—C16—H16 | 123.6 |
C5—C4—H4B | 109.1 | C9—O1—Pd1 | 121.52 (14) |
C3—C4—H4B | 109.1 | C11—O2—Pd1 | 124.93 (14) |
H4A—C4—H4B | 107.9 | F05—P01—F03 | 90.35 (8) |
C6—C5—C4 | 124.47 (19) | F05—P01—F04 | 90.40 (8) |
C6—C5—Pd1 | 71.10 (13) | F03—P01—F04 | 90.13 (8) |
C4—C5—Pd1 | 110.79 (14) | F05—P01—F02 | 90.28 (8) |
C6—C5—H5 | 114.2 | F03—P01—F02 | 90.36 (8) |
C4—C5—H5 | 114.2 | F04—P01—F02 | 179.16 (9) |
Pd1—C5—H5 | 114.2 | F05—P01—F01 | 89.84 (8) |
C5—C6—C7 | 126.5 (2) | F03—P01—F01 | 179.61 (9) |
C5—C6—Pd1 | 72.06 (13) | F04—P01—F01 | 89.52 (8) |
C7—C6—Pd1 | 107.17 (15) | F02—P01—F01 | 89.99 (8) |
C5—C6—H6 | 114.1 | F05—P01—F06 | 179.22 (9) |
C7—C6—H6 | 114.1 | F03—P01—F06 | 90.00 (8) |
Pd1—C6—H6 | 114.1 | F04—P01—F06 | 90.30 (8) |
C6—C7—C8 | 114.01 (18) | F02—P01—F06 | 89.02 (8) |
C6—C7—H7A | 108.8 | F01—P01—F06 | 89.82 (8) |
C8—C7—H7A | 108.8 | C16—S1—C13 | 91.23 (11) |
C6—C7—H7B | 108.8 | O1—Pd1—O2 | 93.43 (6) |
C8—C7—H7B | 108.8 | O1—Pd1—C2 | 88.22 (7) |
H7A—C7—H7B | 107.6 | O2—Pd1—C2 | 158.96 (7) |
C1—C8—C7 | 112.71 (18) | O1—Pd1—C6 | 159.28 (7) |
C1—C8—H8A | 109 | O2—Pd1—C6 | 87.96 (7) |
C7—C8—H8A | 109 | C2—Pd1—C6 | 97.84 (8) |
C1—C8—H8B | 109 | O1—Pd1—C1 | 91.35 (7) |
C7—C8—H8B | 109 | O2—Pd1—C1 | 163.40 (7) |
H8A—C8—H8B | 107.8 | C2—Pd1—C1 | 37.02 (8) |
O1—C9—C10 | 129.8 (2) | C6—Pd1—C1 | 82.04 (8) |
O1—C9—C12 | 111.06 (18) | O1—Pd1—C5 | 163.42 (7) |
C10—C9—C12 | 119.11 (19) | O2—Pd1—C5 | 90.84 (7) |
C9—C10—C11 | 124.8 (2) | C2—Pd1—C5 | 82.16 (8) |
C9—C10—H10 | 117.6 | C6—Pd1—C5 | 36.84 (8) |
C11—C10—H10 | 117.6 | C1—Pd1—C5 | 89.06 (8) |
| | | |
C8—C1—C2—C3 | 5.9 (3) | C9—O1—Pd1—C1 | −161.65 (16) |
Pd1—C1—C2—C3 | −97.4 (2) | C9—O1—Pd1—C5 | 107.1 (3) |
C8—C1—C2—Pd1 | 103.3 (2) | C11—O2—Pd1—O1 | −1.77 (16) |
C1—C2—C3—C4 | 38.1 (3) | C11—O2—Pd1—C2 | −95.7 (2) |
Pd1—C2—C3—C4 | −41.3 (2) | C11—O2—Pd1—C6 | 157.53 (17) |
C2—C3—C4—C5 | 37.9 (3) | C11—O2—Pd1—C1 | 104.7 (3) |
C3—C4—C5—C6 | −95.0 (2) | C11—O2—Pd1—C5 | −165.74 (16) |
C3—C4—C5—Pd1 | −14.2 (2) | C1—C2—Pd1—O1 | 94.61 (13) |
C4—C5—C6—C7 | 4.3 (4) | C3—C2—Pd1—O1 | −141.46 (15) |
Pd1—C5—C6—C7 | −98.4 (2) | C1—C2—Pd1—O2 | −170.45 (17) |
C4—C5—C6—Pd1 | 102.7 (2) | C3—C2—Pd1—O2 | −46.5 (3) |
C5—C6—C7—C8 | 40.9 (3) | C1—C2—Pd1—C6 | −65.49 (14) |
Pd1—C6—C7—C8 | −39.2 (2) | C3—C2—Pd1—C6 | 58.44 (15) |
C2—C1—C8—C7 | −93.7 (2) | C3—C2—Pd1—C1 | 123.9 (2) |
Pd1—C1—C8—C7 | −12.3 (2) | C1—C2—Pd1—C5 | −98.93 (14) |
C6—C7—C8—C1 | 35.2 (3) | C3—C2—Pd1—C5 | 25.00 (15) |
O1—C9—C10—C11 | 0.0 (4) | C5—C6—Pd1—O1 | −171.57 (17) |
C12—C9—C10—C11 | −179.17 (19) | C7—C6—Pd1—O1 | −47.9 (3) |
C9—C10—C11—O2 | 0.9 (3) | C5—C6—Pd1—O2 | 94.12 (13) |
C9—C10—C11—C13 | −178.8 (2) | C7—C6—Pd1—O2 | −142.21 (15) |
O1—C9—C12—F2 | 170.96 (17) | C5—C6—Pd1—C2 | −65.58 (13) |
C10—C9—C12—F2 | −9.7 (3) | C7—C6—Pd1—C2 | 58.09 (15) |
O1—C9—C12—F3 | 49.6 (2) | C5—C6—Pd1—C1 | −99.16 (13) |
C10—C9—C12—F3 | −131.0 (2) | C7—C6—Pd1—C1 | 24.51 (14) |
O1—C9—C12—F1 | −69.2 (2) | C7—C6—Pd1—C5 | 123.7 (2) |
C10—C9—C12—F1 | 110.1 (2) | C2—C1—Pd1—O1 | −85.24 (13) |
O2—C11—C13—C14 | 174.8 (2) | C8—C1—Pd1—O1 | 153.45 (15) |
C10—C11—C13—C14 | −5.5 (3) | C2—C1—Pd1—O2 | 168.0 (2) |
O2—C11—C13—S1 | −4.8 (3) | C8—C1—Pd1—O2 | 46.7 (3) |
C10—C11—C13—S1 | 175.00 (15) | C8—C1—Pd1—C2 | −121.3 (2) |
C11—C13—C14—C15 | −179.7 (2) | C2—C1—Pd1—C6 | 114.47 (14) |
S1—C13—C14—C15 | −0.1 (2) | C8—C1—Pd1—C6 | −6.83 (15) |
C13—C14—C15—C16 | 0.1 (3) | C2—C1—Pd1—C5 | 78.18 (13) |
C14—C15—C16—S1 | 0.0 (3) | C8—C1—Pd1—C5 | −43.13 (15) |
C10—C9—O1—Pd1 | −2.1 (3) | C6—C5—Pd1—O1 | 169.5 (2) |
C12—C9—O1—Pd1 | 177.19 (12) | C4—C5—Pd1—O1 | 48.9 (3) |
C10—C11—O2—Pd1 | 0.5 (3) | C6—C5—Pd1—O2 | −85.48 (13) |
C13—C11—O2—Pd1 | −179.79 (13) | C4—C5—Pd1—O2 | 153.86 (14) |
C15—C16—S1—C13 | −0.07 (18) | C6—C5—Pd1—C2 | 114.42 (14) |
C14—C13—S1—C16 | 0.12 (17) | C4—C5—Pd1—C2 | −6.23 (14) |
C11—C13—S1—C16 | 179.72 (17) | C4—C5—Pd1—C6 | −120.7 (2) |
C9—O1—Pd1—O2 | 2.45 (16) | C6—C5—Pd1—C1 | 77.92 (13) |
C9—O1—Pd1—C2 | 161.45 (16) | C4—C5—Pd1—C1 | −42.74 (15) |
C9—O1—Pd1—C6 | −90.9 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···F2 | 0.95 | 2.33 | 2.712 (3) | 104 |
C14—H14···F01i | 0.95 | 2.32 | 3.193 (3) | 152 |
C5—H5···F01ii | 1 | 2.47 | 3.274 (3) | 137 |
C6—H6···F06iii | 1 | 2.48 | 3.175 (3) | 126 |
C15—H15···F03iv | 0.95 | 2.33 | 3.022 (3) | 129 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x−1, y, z−1; (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·BF4 | F(000) = 1032 |
Mr = 522.56 | Dx = 1.942 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8114 reflections |
a = 10.0528 (3) Å | θ = 2.8–28.4° |
b = 16.6333 (6) Å | µ = 1.24 mm−1 |
c = 13.1600 (3) Å | T = 100 K |
β = 125.684 (2)° | Cuboid, yellow |
V = 1787.35 (9) Å3 | 0.28 × 0.16 × 0.11 mm |
Z = 4 | |
Data collection top
Bruker APEX-II 4K Kappa CCD diffractometer | 4464 independent reflections |
Radiation source: sealed tube | 3873 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 512 pixels mm-1 | θmax = 28.4°, θmin = 3.1° |
ϕ and ω scans | h = −12→13 |
Absorption correction: multi-scan SADABS (Bruker, 2004) | k = −22→22 |
Tmin = 0.724, Tmax = 0.876 | l = −17→17 |
21884 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H-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 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
Crystal data top
C16H16F3O2PdS·BF4 | V = 1787.35 (9) Å3 |
Mr = 522.56 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0528 (3) Å | µ = 1.24 mm−1 |
b = 16.6333 (6) Å | T = 100 K |
c = 13.1600 (3) Å | 0.28 × 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 = 0.876 | Rint = 0.033 |
21884 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.61 e Å−3 |
4464 reflections | Δρmin = −0.73 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.5698 (3) | 0.27486 (13) | 0.8290 (2) | 0.0144 (4) | |
H1 | 0.5284 | 0.25 | 0.8748 | 0.017* | |
C2 | 0.6994 (3) | 0.32719 (14) | 0.9005 (2) | 0.0148 (4) | |
H2 | 0.7339 | 0.3336 | 0.9884 | 0.018* | |
C3 | 0.8351 (3) | 0.34197 (14) | 0.8846 (2) | 0.0165 (5) | |
H3A | 0.8484 | 0.2936 | 0.8475 | 0.02* | |
H3B | 0.9393 | 0.3509 | 0.9678 | 0.02* | |
C4 | 0.7998 (3) | 0.41469 (15) | 0.8011 (2) | 0.0166 (5) | |
H4A | 0.8325 | 0.4641 | 0.8523 | 0.02* | |
H4B | 0.8685 | 0.4108 | 0.7699 | 0.02* | |
C5 | 0.6234 (3) | 0.42259 (15) | 0.6907 (2) | 0.0158 (5) | |
H5 | 0.5959 | 0.4751 | 0.6456 | 0.019* | |
C6 | 0.5166 (3) | 0.36048 (14) | 0.6193 (2) | 0.0155 (5) | |
H6 | 0.4252 | 0.3769 | 0.5324 | 0.019* | |
C7 | 0.5621 (3) | 0.27224 (15) | 0.6315 (2) | 0.0190 (5) | |
H7A | 0.6789 | 0.2677 | 0.6643 | 0.023* | |
H7B | 0.4961 | 0.247 | 0.5477 | 0.023* | |
C8 | 0.5337 (3) | 0.22648 (15) | 0.7191 (2) | 0.0185 (5) | |
H8A | 0.4181 | 0.2086 | 0.6701 | 0.022* | |
H8B | 0.6035 | 0.1778 | 0.7505 | 0.022* | |
C9 | 0.2957 (3) | 0.44979 (13) | 0.8546 (2) | 0.0137 (4) | |
C10 | 0.2083 (3) | 0.50625 (13) | 0.7626 (2) | 0.0148 (4) | |
H10 | 0.1291 | 0.537 | 0.7632 | 0.018* | |
C11 | 0.2289 (3) | 0.52149 (13) | 0.6666 (2) | 0.0127 (4) | |
C12 | 0.2617 (3) | 0.43797 (14) | 0.9529 (2) | 0.0147 (4) | |
C13 | 0.1291 (3) | 0.58218 (14) | 0.5719 (2) | 0.0136 (4) | |
C14 | −0.0021 (3) | 0.62730 (14) | 0.5509 (2) | 0.0168 (5) | |
H14 | −0.0426 | 0.6241 | 0.6004 | 0.02* | |
C15 | −0.0666 (3) | 0.67846 (14) | 0.4460 (2) | 0.0209 (5) | |
H15 | −0.1575 | 0.7131 | 0.4159 | 0.025* | |
C16 | 0.0157 (3) | 0.67274 (14) | 0.3923 (2) | 0.0211 (5) | |
H16 | −0.0108 | 0.7036 | 0.322 | 0.025* | |
B01 | −0.1712 (3) | 0.63633 (17) | 0.7407 (3) | 0.0181 (5) | |
O1 | 0.4068 (2) | 0.40020 (9) | 0.87454 (15) | 0.0148 (3) | |
O2 | 0.33165 (19) | 0.48609 (9) | 0.65401 (15) | 0.0150 (3) | |
F01 | −0.00233 (17) | 0.64810 (9) | 0.80407 (14) | 0.0242 (3) | |
F1 | 0.40033 (16) | 0.44090 (9) | 1.06804 (12) | 0.0195 (3) | |
F2 | 0.19336 (17) | 0.36622 (8) | 0.93805 (13) | 0.0199 (3) | |
F02 | −0.25359 (18) | 0.70539 (9) | 0.67336 (14) | 0.0287 (3) | |
F03 | −0.2058 (2) | 0.62018 (10) | 0.82622 (15) | 0.0314 (4) | |
F3 | 0.16081 (17) | 0.49348 (9) | 0.94621 (13) | 0.0212 (3) | |
F04 | −0.21904 (18) | 0.57198 (9) | 0.65863 (13) | 0.0221 (3) | |
S1 | 0.17045 (8) | 0.60457 (4) | 0.46499 (6) | 0.01898 (13) | |
Pd1 | 0.479840 (19) | 0.396026 (10) | 0.761842 (15) | 0.01125 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0166 (11) | 0.0113 (11) | 0.0151 (11) | 0.0038 (8) | 0.0092 (10) | 0.0050 (9) |
C2 | 0.0144 (11) | 0.0160 (11) | 0.0111 (11) | 0.0043 (9) | 0.0057 (9) | 0.0045 (9) |
C3 | 0.0114 (10) | 0.0220 (12) | 0.0137 (11) | 0.0017 (9) | 0.0059 (9) | 0.0020 (9) |
C4 | 0.0126 (11) | 0.0218 (12) | 0.0157 (12) | −0.0017 (9) | 0.0084 (10) | −0.0005 (10) |
C5 | 0.0152 (11) | 0.0222 (12) | 0.0135 (11) | 0.0030 (9) | 0.0103 (10) | 0.0058 (9) |
C6 | 0.0143 (11) | 0.0229 (13) | 0.0091 (11) | 0.0026 (9) | 0.0067 (9) | 0.0032 (9) |
C7 | 0.0209 (12) | 0.0212 (13) | 0.0147 (12) | 0.0016 (10) | 0.0103 (10) | −0.0035 (10) |
C8 | 0.0170 (11) | 0.0167 (12) | 0.0184 (12) | 0.0020 (9) | 0.0084 (10) | −0.0010 (10) |
C9 | 0.0141 (10) | 0.0130 (11) | 0.0156 (11) | −0.0034 (8) | 0.0096 (9) | −0.0026 (9) |
C10 | 0.0136 (10) | 0.0149 (11) | 0.0166 (11) | 0.0008 (9) | 0.0093 (9) | 0.0003 (9) |
C11 | 0.0099 (10) | 0.0101 (10) | 0.0135 (11) | −0.0008 (8) | 0.0042 (9) | −0.0007 (8) |
C12 | 0.0152 (11) | 0.0143 (11) | 0.0164 (11) | 0.0000 (9) | 0.0103 (10) | 0.0001 (9) |
C13 | 0.0130 (10) | 0.0134 (11) | 0.0128 (11) | −0.0015 (8) | 0.0065 (9) | 0.0003 (9) |
C14 | 0.0138 (11) | 0.0145 (11) | 0.0171 (12) | −0.0013 (9) | 0.0061 (10) | 0.0013 (9) |
C15 | 0.0182 (12) | 0.0148 (12) | 0.0226 (13) | 0.0021 (9) | 0.0079 (11) | −0.0003 (10) |
C16 | 0.0240 (13) | 0.0143 (12) | 0.0155 (12) | −0.0001 (10) | 0.0061 (11) | 0.0018 (9) |
B01 | 0.0208 (13) | 0.0166 (13) | 0.0159 (13) | 0.0017 (11) | 0.0101 (12) | −0.0010 (11) |
O1 | 0.0156 (8) | 0.0161 (8) | 0.0158 (8) | 0.0039 (6) | 0.0109 (7) | 0.0034 (6) |
O2 | 0.0143 (8) | 0.0155 (8) | 0.0148 (8) | 0.0023 (6) | 0.0082 (7) | 0.0025 (6) |
F01 | 0.0173 (7) | 0.0267 (8) | 0.0219 (8) | 0.0021 (6) | 0.0077 (6) | −0.0058 (6) |
F1 | 0.0160 (7) | 0.0268 (8) | 0.0126 (7) | −0.0018 (6) | 0.0066 (6) | 0.0001 (6) |
F2 | 0.0228 (7) | 0.0198 (7) | 0.0220 (8) | −0.0054 (6) | 0.0157 (7) | −0.0014 (6) |
F02 | 0.0255 (8) | 0.0210 (8) | 0.0255 (8) | 0.0057 (6) | 0.0069 (7) | 0.0019 (6) |
F03 | 0.0381 (9) | 0.0393 (9) | 0.0263 (9) | −0.0036 (7) | 0.0242 (8) | −0.0045 (7) |
F3 | 0.0240 (7) | 0.0232 (8) | 0.0229 (8) | 0.0073 (6) | 0.0173 (7) | 0.0022 (6) |
F04 | 0.0289 (8) | 0.0180 (7) | 0.0183 (7) | −0.0035 (6) | 0.0131 (7) | −0.0037 (6) |
S1 | 0.0218 (3) | 0.0182 (3) | 0.0169 (3) | 0.0032 (2) | 0.0112 (3) | 0.0036 (2) |
Pd1 | 0.01058 (9) | 0.01181 (10) | 0.01148 (10) | 0.00138 (6) | 0.00650 (8) | 0.00158 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.382 (3) | C9—O1 | 1.286 (3) |
C1—C8 | 1.503 (3) | C9—C10 | 1.371 (3) |
C1—Pd1 | 2.174 (2) | C9—C12 | 1.532 (3) |
C1—H1 | 1 | C10—C11 | 1.416 (3) |
C2—C3 | 1.516 (3) | C10—H10 | 0.95 |
C2—Pd1 | 2.194 (2) | C11—O2 | 1.282 (3) |
C2—H2 | 1 | C11—C13 | 1.456 (3) |
C3—C4 | 1.531 (3) | C12—F1 | 1.333 (3) |
C3—H3A | 0.99 | C12—F2 | 1.333 (3) |
C3—H3B | 0.99 | C12—F3 | 1.336 (2) |
C4—C5 | 1.506 (3) | C13—C14 | 1.399 (3) |
C4—H4A | 0.99 | C13—S1 | 1.724 (2) |
C4—H4B | 0.99 | C14—C15 | 1.417 (3) |
C5—C6 | 1.388 (3) | C14—H14 | 0.95 |
C5—Pd1 | 2.174 (2) | C15—C16 | 1.369 (3) |
C5—H5 | 1 | C15—H15 | 0.95 |
C6—C7 | 1.518 (3) | C16—S1 | 1.698 (3) |
C6—Pd1 | 2.194 (2) | C16—H16 | 0.95 |
C6—H6 | 1 | B01—F03 | 1.384 (3) |
C7—C8 | 1.540 (3) | B01—F02 | 1.391 (3) |
C7—H7A | 0.99 | B01—F04 | 1.392 (3) |
C7—H7B | 0.99 | B01—F01 | 1.402 (3) |
C8—H8A | 0.99 | O1—Pd1 | 2.0032 (15) |
C8—H8B | 0.99 | O2—Pd1 | 2.0028 (15) |
| | | |
C2—C1—C8 | 126.6 (2) | C10—C9—C12 | 119.33 (19) |
C2—C1—Pd1 | 72.33 (13) | C9—C10—C11 | 123.9 (2) |
C8—C1—Pd1 | 107.20 (15) | C9—C10—H10 | 118 |
C2—C1—H1 | 114 | C11—C10—H10 | 118 |
C8—C1—H1 | 114 | O2—C11—C10 | 125.6 (2) |
Pd1—C1—H1 | 114 | O2—C11—C13 | 114.33 (19) |
C1—C2—C3 | 125.0 (2) | C10—C11—C13 | 120.11 (19) |
C1—C2—Pd1 | 70.78 (13) | F1—C12—F2 | 107.87 (18) |
C3—C2—Pd1 | 110.49 (15) | F1—C12—F3 | 107.43 (18) |
C1—C2—H2 | 114.1 | F2—C12—F3 | 107.61 (17) |
C3—C2—H2 | 114.1 | F1—C12—C9 | 110.80 (17) |
Pd1—C2—H2 | 114.1 | F2—C12—C9 | 109.94 (18) |
C2—C3—C4 | 112.16 (18) | F3—C12—C9 | 113.00 (18) |
C2—C3—H3A | 109.2 | C14—C13—C11 | 129.8 (2) |
C4—C3—H3A | 109.2 | C14—C13—S1 | 111.82 (17) |
C2—C3—H3B | 109.2 | C11—C13—S1 | 118.38 (16) |
C4—C3—H3B | 109.2 | C13—C14—C15 | 110.9 (2) |
H3A—C3—H3B | 107.9 | C13—C14—H14 | 124.5 |
C5—C4—C3 | 114.25 (19) | C15—C14—H14 | 124.5 |
C5—C4—H4A | 108.7 | C16—C15—C14 | 113.0 (2) |
C3—C4—H4A | 108.7 | C16—C15—H15 | 123.5 |
C5—C4—H4B | 108.7 | C14—C15—H15 | 123.5 |
C3—C4—H4B | 108.7 | C15—C16—S1 | 112.72 (19) |
H4A—C4—H4B | 107.6 | C15—C16—H16 | 123.6 |
C6—C5—C4 | 126.8 (2) | S1—C16—H16 | 123.6 |
C6—C5—Pd1 | 72.23 (12) | F03—B01—F02 | 109.9 (2) |
C4—C5—Pd1 | 105.75 (14) | F03—B01—F04 | 110.2 (2) |
C6—C5—H5 | 114.3 | F02—B01—F04 | 109.4 (2) |
C4—C5—H5 | 114.3 | F03—B01—F01 | 109.6 (2) |
Pd1—C5—H5 | 114.3 | F02—B01—F01 | 109.2 (2) |
C5—C6—C7 | 125.6 (2) | F04—B01—F01 | 108.62 (19) |
C5—C6—Pd1 | 70.72 (12) | C9—O1—Pd1 | 121.37 (14) |
C7—C6—Pd1 | 111.15 (14) | C11—O2—Pd1 | 125.07 (14) |
C5—C6—H6 | 113.8 | C16—S1—C13 | 91.52 (12) |
C7—C6—H6 | 113.8 | O2—Pd1—O1 | 93.23 (6) |
Pd1—C6—H6 | 113.8 | O2—Pd1—C1 | 160.45 (8) |
C6—C7—C8 | 112.40 (18) | O1—Pd1—C1 | 88.65 (7) |
C6—C7—H7A | 109.1 | O2—Pd1—C5 | 87.08 (8) |
C8—C7—H7A | 109.1 | O1—Pd1—C5 | 158.94 (8) |
C6—C7—H7B | 109.1 | C1—Pd1—C5 | 98.05 (9) |
C8—C7—H7B | 109.1 | O2—Pd1—C6 | 91.28 (7) |
H7A—C7—H7B | 107.9 | O1—Pd1—C6 | 163.63 (8) |
C1—C8—C7 | 114.1 (2) | C1—Pd1—C6 | 81.96 (8) |
C1—C8—H8A | 108.7 | C5—Pd1—C6 | 37.05 (9) |
C7—C8—H8A | 108.7 | O2—Pd1—C2 | 162.05 (8) |
C1—C8—H8B | 108.7 | O1—Pd1—C2 | 91.56 (7) |
C7—C8—H8B | 108.7 | C1—Pd1—C2 | 36.89 (8) |
H8A—C8—H8B | 107.6 | C5—Pd1—C2 | 82.31 (8) |
O1—C9—C10 | 130.8 (2) | C6—Pd1—C2 | 88.94 (8) |
O1—C9—C12 | 109.90 (19) | | |
| | | |
C8—C1—C2—C3 | −3.4 (4) | C11—O2—Pd1—C6 | 160.73 (18) |
Pd1—C1—C2—C3 | −102.0 (2) | C11—O2—Pd1—C2 | −108.8 (3) |
C8—C1—C2—Pd1 | 98.6 (2) | C9—O1—Pd1—O2 | 1.83 (17) |
C1—C2—C3—C4 | 94.5 (3) | C9—O1—Pd1—C1 | −158.70 (18) |
Pd1—C2—C3—C4 | 14.2 (2) | C9—O1—Pd1—C5 | 92.1 (3) |
C2—C3—C4—C5 | −39.0 (3) | C9—O1—Pd1—C6 | −103.9 (3) |
C3—C4—C5—C6 | −36.9 (3) | C9—O1—Pd1—C2 | 164.52 (17) |
C3—C4—C5—Pd1 | 42.5 (2) | C2—C1—Pd1—O2 | 169.74 (18) |
C4—C5—C6—C7 | −6.0 (3) | C8—C1—Pd1—O2 | 46.0 (3) |
Pd1—C5—C6—C7 | −102.7 (2) | C2—C1—Pd1—O1 | −94.40 (13) |
C4—C5—C6—Pd1 | 96.7 (2) | C8—C1—Pd1—O1 | 141.84 (15) |
C5—C6—C7—C8 | 93.6 (3) | C2—C1—Pd1—C5 | 65.56 (14) |
Pd1—C6—C7—C8 | 12.7 (2) | C8—C1—Pd1—C5 | −58.20 (16) |
C2—C1—C8—C7 | −40.5 (3) | C2—C1—Pd1—C6 | 99.04 (14) |
Pd1—C1—C8—C7 | 39.9 (2) | C8—C1—Pd1—C6 | −24.72 (15) |
C6—C7—C8—C1 | −35.9 (3) | C8—C1—Pd1—C2 | −123.8 (2) |
O1—C9—C10—C11 | −0.9 (4) | C6—C5—Pd1—O2 | −96.00 (14) |
C12—C9—C10—C11 | −179.4 (2) | C4—C5—Pd1—O2 | 139.72 (16) |
C9—C10—C11—O2 | −1.0 (4) | C6—C5—Pd1—O1 | 172.58 (18) |
C9—C10—C11—C13 | 179.4 (2) | C4—C5—Pd1—O1 | 48.3 (3) |
O1—C9—C12—F1 | 52.3 (2) | C6—C5—Pd1—C1 | 65.04 (15) |
C10—C9—C12—F1 | −128.9 (2) | C4—C5—Pd1—C1 | −59.24 (17) |
O1—C9—C12—F2 | −66.8 (2) | C4—C5—Pd1—C6 | −124.3 (2) |
C10—C9—C12—F2 | 112.0 (2) | C6—C5—Pd1—C2 | 98.51 (15) |
O1—C9—C12—F3 | 172.96 (18) | C4—C5—Pd1—C2 | −25.77 (16) |
C10—C9—C12—F3 | −8.3 (3) | C5—C6—Pd1—O2 | 83.45 (14) |
O2—C11—C13—C14 | 174.3 (2) | C7—C6—Pd1—O2 | −154.86 (16) |
C10—C11—C13—C14 | −6.1 (4) | C5—C6—Pd1—O1 | −170.5 (2) |
O2—C11—C13—S1 | −5.0 (3) | C7—C6—Pd1—O1 | −48.8 (3) |
C10—C11—C13—S1 | 174.60 (17) | C5—C6—Pd1—C1 | −114.96 (15) |
C11—C13—C14—C15 | −178.6 (2) | C7—C6—Pd1—C1 | 6.73 (16) |
S1—C13—C14—C15 | 0.8 (3) | C7—C6—Pd1—C5 | 121.7 (2) |
C13—C14—C15—C16 | −1.1 (3) | C5—C6—Pd1—C2 | −78.60 (14) |
C14—C15—C16—S1 | 1.0 (3) | C7—C6—Pd1—C2 | 43.09 (16) |
C10—C9—O1—Pd1 | −0.1 (3) | C1—C2—Pd1—O2 | −168.8 (2) |
C12—C9—O1—Pd1 | 178.45 (13) | C3—C2—Pd1—O2 | −47.6 (3) |
C10—C11—O2—Pd1 | 3.6 (3) | C1—C2—Pd1—O1 | 85.67 (13) |
C13—C11—O2—Pd1 | −176.77 (14) | C3—C2—Pd1—O1 | −153.07 (16) |
C15—C16—S1—C13 | −0.5 (2) | C3—C2—Pd1—C1 | 121.3 (2) |
C14—C13—S1—C16 | −0.19 (19) | C1—C2—Pd1—C5 | −114.55 (14) |
C11—C13—S1—C16 | 179.27 (19) | C3—C2—Pd1—C5 | 6.71 (16) |
C11—O2—Pd1—O1 | −3.53 (18) | C1—C2—Pd1—C6 | −77.97 (14) |
C11—O2—Pd1—C1 | 91.5 (3) | C3—C2—Pd1—C6 | 43.30 (17) |
C11—O2—Pd1—C5 | −162.45 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···F01 | 0.95 | 2.51 | 3.420 (3) | 162 |
C10—H10···F3 | 0.95 | 2.35 | 2.731 (2) | 103 |
C14—H14···F01 | 0.95 | 2.5 | 3.351 (3) | 149 |
C14—H14···F04 | 0.95 | 2.46 | 3.349 (3) | 155 |
C2—H2···F01i | 1 | 2.5 | 3.278 (3) | 135 |
C3—H3B···F03i | 0.99 | 2.51 | 3.496 (3) | 177 |
C5—H5···F04ii | 1 | 2.39 | 3.106 (3) | 128 |
C6—H6···F04iii | 1 | 2.29 | 3.290 (3) | 174 |
C16—H16···F01iv | 0.95 | 2.48 | 3.165 (3) | 129 |
C16—H16···F02iv | 0.95 | 2.55 | 3.262 (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, z−1/2. |
(10ath3_0m) (hexafluoroacetylacetonato)(
η4-
cyclo-octa-1,5-dienyl)palladium(II) hexafluorophosphate
top
Crystal data top
C13H13F6O2Pd·F6P | F(000) = 1104 |
Mr = 566.6 | Dx = 2.128 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8161 reflections |
a = 8.5885 (2) Å | θ = 2.8–32.6° |
b = 10.6304 (2) Å | µ = 1.27 mm−1 |
c = 19.4093 (4) Å | T = 100 K |
β = 93.415 (1)° | Plate, yellow |
V = 1768.91 (6) Å3 | 0.38 × 0.22 × 0.07 mm |
Z = 4 | |
Data collection top
Bruker APEX-II 4K Kappa CCD diffractometer | 4248 independent reflections |
Radiation source: sealed tube | 3805 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 512 pixels mm-1 | θmax = 28°, θmin = 2.4° |
ϕ and ω scans | h = −11→11 |
Absorption correction: multi-scan SADABS (Bruker, 2004) | k = −14→13 |
Tmin = 0.644, Tmax = 0.916 | l = −25→25 |
16999 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H-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 parameters | Δρmax = 0.60 e Å−3 |
1 restraint | Δρmin = −0.65 e Å−3 |
Crystal data top
C13H13F6O2Pd·F6P | V = 1768.91 (6) Å3 |
Mr = 566.6 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.5885 (2) Å | µ = 1.27 mm−1 |
b = 10.6304 (2) Å | T = 100 K |
c = 19.4093 (4) Å | 0.38 × 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 = 0.916 | Rint = 0.029 |
16999 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.025 | 1 restraint |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.60 e Å−3 |
4248 reflections | Δρmin = −0.65 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.4159 (3) | 0.0840 (2) | 0.29214 (11) | 0.0193 (4) | |
H1 | 0.4943 | 0.1465 | 0.2774 | 0.023* | |
C2 | 0.2635 (3) | 0.1129 (2) | 0.27037 (11) | 0.0204 (4) | |
H2 | 0.2527 | 0.1917 | 0.2424 | 0.024* | |
C3 | 0.1305 (3) | 0.0219 (2) | 0.25781 (11) | 0.0236 (5) | |
H3A | 0.1356 | −0.0142 | 0.211 | 0.028* | |
H3B | 0.0309 | 0.0684 | 0.2592 | 0.028* | |
C4 | 0.1312 (3) | −0.0856 (2) | 0.31034 (12) | 0.0245 (5) | |
H4A | 0.0253 | −0.1223 | 0.3104 | 0.029* | |
H4B | 0.2032 | −0.1523 | 0.2963 | 0.029* | |
C5 | 0.1811 (3) | −0.0420 (2) | 0.38289 (11) | 0.0204 (4) | |
H5 | 0.098 | −0.0499 | 0.4166 | 0.024* | |
C6 | 0.3315 (3) | −0.0484 (2) | 0.41255 (12) | 0.0208 (4) | |
H6 | 0.3371 | −0.0611 | 0.4637 | 0.025* | |
C7 | 0.4755 (3) | −0.0901 (2) | 0.37814 (13) | 0.0239 (5) | |
H7A | 0.4813 | −0.1831 | 0.3797 | 0.029* | |
H7B | 0.5685 | −0.0568 | 0.4047 | 0.029* | |
C8 | 0.4806 (3) | −0.0473 (2) | 0.30292 (12) | 0.0232 (5) | |
H8A | 0.5899 | −0.0493 | 0.2893 | 0.028* | |
H8B | 0.4194 | −0.1067 | 0.2728 | 0.028* | |
C9 | 0.2922 (2) | 0.4149 (2) | 0.40118 (11) | 0.0179 (4) | |
C10 | 0.2408 (3) | 0.4066 (2) | 0.46716 (12) | 0.0206 (4) | |
H10 | 0.2216 | 0.4823 | 0.4913 | 0.025* | |
C11 | 0.2159 (2) | 0.2923 (2) | 0.49978 (11) | 0.0183 (4) | |
C12 | 0.3198 (3) | 0.5460 (2) | 0.37152 (13) | 0.0251 (5) | |
C13 | 0.1586 (3) | 0.2993 (2) | 0.57296 (12) | 0.0234 (5) | |
O1 | 0.31948 (18) | 0.32899 (14) | 0.35832 (8) | 0.0184 (3) | |
O2 | 0.23469 (18) | 0.18173 (15) | 0.47876 (8) | 0.0187 (3) | |
F01 | −0.1961 (3) | 0.3528 (2) | 0.42928 (14) | 0.0760 (8) | |
F02 | −0.1072 (2) | 0.1628 (3) | 0.46033 (11) | 0.0798 (9) | |
F03 | −0.03143 (16) | 0.25360 (14) | 0.36249 (8) | 0.0303 (3) | |
F04 | −0.28470 (19) | 0.2749 (2) | 0.32642 (9) | 0.0526 (5) | |
F05 | −0.36114 (16) | 0.18714 (16) | 0.42473 (8) | 0.0312 (3) | |
F06 | −0.1929 (2) | 0.08614 (17) | 0.35887 (13) | 0.0636 (6) | |
P01 | −0.19615 (7) | 0.22092 (6) | 0.39388 (3) | 0.01978 (12) | |
Pd1 | 0.288665 (19) | 0.144660 (15) | 0.380626 (8) | 0.01539 (6) | |
F3 | 0.3059 (2) | 0.63734 (14) | 0.41678 (9) | 0.0426 (4) | |
F1 | 0.46128 (19) | 0.55329 (15) | 0.34792 (9) | 0.0413 (4) | |
F2 | 0.2197 (2) | 0.56862 (16) | 0.31814 (10) | 0.0510 (5) | |
F4 | 0.2685 (3) | 0.3564 (3) | 0.61449 (10) | 0.0331 (7) | 0.757 (6) |
F5 | 0.0308 (3) | 0.3603 (5) | 0.57533 (13) | 0.0448 (10) | 0.757 (6) |
F6 | 0.1453 (5) | 0.1845 (2) | 0.59988 (13) | 0.0401 (8) | 0.757 (6) |
F4B | 0.254 (2) | 0.295 (2) | 0.6198 (7) | 0.0331 (7) | 0.115 (4) |
F5B | −0.0035 (16) | 0.281 (3) | 0.5731 (8) | 0.024 (4) | 0.115 (4) |
F6B | 0.180 (3) | 0.4104 (14) | 0.6067 (8) | 0.0401 (8) | 0.115 (4) |
F4C | 0.2190 (17) | 0.2251 (19) | 0.6177 (6) | 0.0331 (7) | 0.128 (4) |
F5C | 0.039 (4) | 0.2199 (18) | 0.5798 (11) | 0.048 (7) | 0.128 (4) |
F6C | 0.068 (3) | 0.4122 (15) | 0.5823 (10) | 0.0401 (8) | 0.128 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0252 (11) | 0.0215 (11) | 0.0120 (10) | −0.0032 (9) | 0.0067 (8) | −0.0021 (8) |
C2 | 0.0283 (11) | 0.0254 (11) | 0.0075 (9) | −0.0001 (9) | 0.0029 (8) | −0.0020 (8) |
C3 | 0.0237 (11) | 0.0331 (13) | 0.0138 (10) | −0.0022 (9) | −0.0011 (9) | −0.0051 (9) |
C4 | 0.0259 (11) | 0.0310 (13) | 0.0169 (11) | −0.0103 (10) | 0.0045 (9) | −0.0046 (9) |
C5 | 0.0252 (11) | 0.0210 (11) | 0.0155 (10) | −0.0088 (9) | 0.0054 (8) | −0.0011 (8) |
C6 | 0.0314 (12) | 0.0147 (10) | 0.0161 (10) | −0.0036 (9) | 0.0002 (9) | 0.0025 (8) |
C7 | 0.0262 (11) | 0.0175 (11) | 0.0275 (12) | −0.0005 (9) | −0.0017 (9) | 0.0011 (9) |
C8 | 0.0224 (11) | 0.0225 (11) | 0.0252 (12) | −0.0005 (9) | 0.0044 (9) | −0.0053 (9) |
C9 | 0.0163 (10) | 0.0192 (10) | 0.0181 (10) | −0.0015 (8) | −0.0004 (8) | 0.0001 (8) |
C10 | 0.0233 (11) | 0.0196 (11) | 0.0195 (11) | −0.0028 (8) | 0.0043 (9) | −0.0043 (9) |
C11 | 0.0170 (10) | 0.0248 (11) | 0.0131 (10) | −0.0034 (8) | 0.0014 (8) | −0.0020 (8) |
C12 | 0.0309 (12) | 0.0205 (11) | 0.0245 (12) | −0.0038 (9) | 0.0069 (10) | 0.0002 (9) |
C13 | 0.0285 (12) | 0.0256 (12) | 0.0162 (11) | −0.0054 (9) | 0.0040 (9) | −0.0036 (9) |
O1 | 0.0239 (8) | 0.0178 (7) | 0.0138 (7) | 0.0003 (6) | 0.0032 (6) | 0.0009 (6) |
O2 | 0.0252 (8) | 0.0198 (7) | 0.0112 (7) | −0.0021 (6) | 0.0010 (6) | −0.0010 (6) |
F01 | 0.0679 (14) | 0.0589 (14) | 0.106 (2) | −0.0280 (11) | 0.0448 (13) | −0.0577 (13) |
F02 | 0.0312 (10) | 0.159 (3) | 0.0480 (12) | −0.0065 (12) | −0.0068 (9) | 0.0616 (14) |
F03 | 0.0228 (7) | 0.0382 (8) | 0.0300 (8) | −0.0049 (6) | 0.0033 (6) | 0.0037 (7) |
F04 | 0.0308 (9) | 0.0821 (14) | 0.0433 (10) | −0.0123 (9) | −0.0100 (7) | 0.0405 (10) |
F05 | 0.0228 (7) | 0.0443 (9) | 0.0267 (8) | −0.0028 (6) | 0.0033 (6) | 0.0075 (7) |
F06 | 0.0633 (13) | 0.0298 (9) | 0.1020 (17) | −0.0129 (9) | 0.0402 (12) | −0.0194 (10) |
P01 | 0.0194 (3) | 0.0231 (3) | 0.0167 (3) | −0.0017 (2) | −0.0008 (2) | 0.0011 (2) |
Pd1 | 0.02091 (9) | 0.01564 (9) | 0.00963 (9) | −0.00119 (6) | 0.00091 (6) | −0.00051 (6) |
F3 | 0.0685 (12) | 0.0196 (8) | 0.0425 (10) | −0.0097 (7) | 0.0276 (9) | −0.0063 (7) |
F1 | 0.0412 (9) | 0.0323 (9) | 0.0533 (11) | −0.0077 (7) | 0.0272 (8) | 0.0052 (8) |
F2 | 0.0666 (12) | 0.0335 (9) | 0.0502 (11) | −0.0021 (8) | −0.0198 (9) | 0.0200 (8) |
F4 | 0.0376 (12) | 0.0486 (18) | 0.0129 (9) | −0.0169 (12) | 0.0000 (7) | −0.0074 (10) |
F5 | 0.0292 (17) | 0.081 (3) | 0.0251 (13) | 0.0207 (19) | 0.0082 (11) | −0.0037 (18) |
F6 | 0.073 (2) | 0.0258 (12) | 0.0251 (12) | −0.0095 (15) | 0.0293 (14) | −0.0015 (10) |
F4B | 0.0376 (12) | 0.0486 (18) | 0.0129 (9) | −0.0169 (12) | 0.0000 (7) | −0.0074 (10) |
F5B | 0.005 (6) | 0.044 (12) | 0.022 (7) | −0.003 (7) | 0.004 (4) | −0.013 (9) |
F6B | 0.073 (2) | 0.0258 (12) | 0.0251 (12) | −0.0095 (15) | 0.0293 (14) | −0.0015 (10) |
F4C | 0.0376 (12) | 0.0486 (18) | 0.0129 (9) | −0.0169 (12) | 0.0000 (7) | −0.0074 (10) |
F5C | 0.093 (18) | 0.017 (9) | 0.040 (11) | −0.022 (9) | 0.059 (12) | −0.017 (8) |
F6C | 0.073 (2) | 0.0258 (12) | 0.0251 (12) | −0.0095 (15) | 0.0293 (14) | −0.0015 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.386 (3) | C9—C12 | 1.531 (3) |
C1—C8 | 1.512 (3) | C10—C11 | 1.393 (3) |
C1—Pd1 | 2.187 (2) | C10—H10 | 0.95 |
C1—H1 | 1 | C11—O2 | 1.258 (3) |
C2—C3 | 1.505 (3) | C11—C13 | 1.533 (3) |
C2—Pd1 | 2.164 (2) | C12—F3 | 1.320 (3) |
C2—H2 | 1 | C12—F1 | 1.326 (3) |
C3—C4 | 1.531 (3) | C12—F2 | 1.329 (3) |
C3—H3A | 0.99 | C13—F4B | 1.186 (16) |
C3—H3B | 0.99 | C13—F4C | 1.262 (14) |
C4—C5 | 1.520 (3) | C13—F5 | 1.277 (4) |
C4—H4A | 0.99 | C13—F6 | 1.335 (4) |
C4—H4B | 0.99 | C13—F5C | 1.344 (18) |
C5—C6 | 1.384 (3) | C13—F4 | 1.348 (3) |
C5—Pd1 | 2.190 (2) | C13—F6B | 1.357 (15) |
C5—H5 | 1 | C13—F5B | 1.407 (14) |
C6—C7 | 1.507 (3) | C13—F6C | 1.45 (2) |
C6—Pd1 | 2.169 (2) | O1—Pd1 | 2.0275 (15) |
C6—H6 | 1 | O2—Pd1 | 2.0257 (15) |
C7—C8 | 1.532 (3) | F01—P01 | 1.5610 (19) |
C7—H7A | 0.99 | F02—P01 | 1.5852 (18) |
C7—H7B | 0.99 | F03—P01 | 1.6112 (15) |
C8—H8A | 0.99 | F04—P01 | 1.5820 (16) |
C8—H8B | 0.99 | F05—P01 | 1.6114 (15) |
C9—O1 | 1.267 (3) | F06—P01 | 1.5867 (19) |
C9—C10 | 1.382 (3) | | |
| | | |
C2—C1—C8 | 125.4 (2) | F4C—C13—F5C | 79.9 (15) |
C2—C1—Pd1 | 70.55 (12) | F5—C13—F5C | 69.6 (13) |
C8—C1—Pd1 | 111.12 (15) | F6—C13—F5C | 45.8 (14) |
C2—C1—H1 | 113.9 | F4B—C13—F4 | 29.8 (12) |
C8—C1—H1 | 113.9 | F4C—C13—F4 | 68.0 (9) |
Pd1—C1—H1 | 113.9 | F5—C13—F4 | 108.8 (3) |
C1—C2—C3 | 126.9 (2) | F6—C13—F4 | 104.5 (2) |
C1—C2—Pd1 | 72.32 (12) | F5C—C13—F4 | 137.4 (10) |
C3—C2—Pd1 | 106.91 (14) | F4B—C13—F6B | 66.1 (14) |
C1—C2—H2 | 114 | F4C—C13—F6B | 100.0 (11) |
C3—C2—H2 | 114 | F5—C13—F6B | 68.5 (11) |
Pd1—C2—H2 | 114 | F6—C13—F6B | 128.2 (7) |
C2—C3—C4 | 113.51 (18) | F5C—C13—F6B | 125.6 (10) |
C2—C3—H3A | 108.9 | F4—C13—F6B | 41.4 (11) |
C4—C3—H3A | 108.9 | F4B—C13—F5B | 129.1 (11) |
C2—C3—H3B | 108.9 | F4C—C13—F5B | 106.1 (11) |
C4—C3—H3B | 108.9 | F5—C13—F5B | 38.7 (11) |
H3A—C3—H3B | 107.7 | F6—C13—F5B | 76.2 (11) |
C5—C4—C3 | 112.27 (19) | F5C—C13—F5B | 31.5 (11) |
C5—C4—H4A | 109.1 | F4—C13—F5B | 136.1 (8) |
C3—C4—H4A | 109.1 | F6B—C13—F5B | 103.2 (12) |
C5—C4—H4B | 109.1 | F4B—C13—F6C | 106.5 (13) |
C3—C4—H4B | 109.1 | F4C—C13—F6C | 129.4 (10) |
H4A—C4—H4B | 107.9 | F5—C13—F6C | 26.7 (9) |
C6—C5—C4 | 125.1 (2) | F6—C13—F6C | 130.6 (7) |
C6—C5—Pd1 | 70.67 (12) | F5C—C13—F6C | 95.2 (13) |
C4—C5—Pd1 | 110.72 (15) | F4—C13—F6C | 85.0 (10) |
C6—C5—H5 | 114.1 | F6B—C13—F6C | 43.6 (10) |
C4—C5—H5 | 114.1 | F5B—C13—F6C | 65.1 (12) |
Pd1—C5—H5 | 114.1 | F4B—C13—C11 | 117.6 (8) |
C5—C6—C7 | 126.9 (2) | F4C—C13—C11 | 117.8 (6) |
C5—C6—Pd1 | 72.30 (13) | F5—C13—C11 | 112.5 (2) |
C7—C6—Pd1 | 106.36 (14) | F6—C13—C11 | 111.0 (2) |
C5—C6—H6 | 114.1 | F5C—C13—C11 | 110.6 (7) |
C7—C6—H6 | 114.1 | F4—C13—C11 | 108.9 (2) |
Pd1—C6—H6 | 114.1 | F6B—C13—C11 | 116.6 (6) |
C6—C7—C8 | 113.94 (19) | F5B—C13—C11 | 111.6 (6) |
C6—C7—H7A | 108.8 | F6C—C13—C11 | 111.1 (7) |
C8—C7—H7A | 108.8 | C9—O1—Pd1 | 121.67 (14) |
C6—C7—H7B | 108.8 | C11—O2—Pd1 | 121.85 (14) |
C8—C7—H7B | 108.8 | F01—P01—F04 | 91.50 (15) |
H7A—C7—H7B | 107.7 | F01—P01—F02 | 90.26 (16) |
C1—C8—C7 | 112.02 (19) | F04—P01—F02 | 178.23 (15) |
C1—C8—H8A | 109.2 | F01—P01—F06 | 178.78 (15) |
C7—C8—H8A | 109.2 | F04—P01—F06 | 89.59 (13) |
C1—C8—H8B | 109.2 | F02—P01—F06 | 88.65 (15) |
C7—C8—H8B | 109.2 | F01—P01—F03 | 89.76 (10) |
H8A—C8—H8B | 107.9 | F04—P01—F03 | 89.91 (8) |
O1—C9—C10 | 130.1 (2) | F02—P01—F03 | 90.00 (9) |
O1—C9—C12 | 111.73 (19) | F06—P01—F03 | 89.69 (9) |
C10—C9—C12 | 118.1 (2) | F01—P01—F05 | 90.77 (10) |
C9—C10—C11 | 122.9 (2) | F04—P01—F05 | 89.91 (8) |
C9—C10—H10 | 118.6 | F02—P01—F05 | 90.16 (9) |
C11—C10—H10 | 118.6 | F06—P01—F05 | 89.78 (10) |
O2—C11—C10 | 129.9 (2) | F03—P01—F05 | 179.44 (9) |
O2—C11—C13 | 113.63 (19) | O2—Pd1—O1 | 93.03 (6) |
C10—C11—C13 | 116.4 (2) | O2—Pd1—C2 | 160.90 (8) |
F3—C12—F1 | 107.9 (2) | O1—Pd1—C2 | 86.93 (8) |
F3—C12—F2 | 107.8 (2) | O2—Pd1—C6 | 87.70 (8) |
F1—C12—F2 | 106.5 (2) | O1—Pd1—C6 | 162.45 (8) |
F3—C12—C9 | 113.4 (2) | C2—Pd1—C6 | 98.05 (9) |
F1—C12—C9 | 110.4 (2) | O2—Pd1—C1 | 161.58 (7) |
F2—C12—C9 | 110.52 (19) | O1—Pd1—C1 | 92.27 (7) |
F4B—C13—F4C | 38.2 (10) | C2—Pd1—C1 | 37.14 (8) |
F4B—C13—F5 | 123.0 (9) | C6—Pd1—C1 | 82.01 (9) |
F4C—C13—F5 | 127.7 (6) | O2—Pd1—C5 | 92.11 (7) |
F4B—C13—F6 | 74.8 (12) | O1—Pd1—C5 | 160.11 (8) |
F4C—C13—F6 | 36.9 (8) | C2—Pd1—C5 | 82.01 (8) |
F5—C13—F6 | 110.8 (3) | C6—Pd1—C5 | 37.03 (8) |
F4B—C13—F5C | 113.4 (15) | C1—Pd1—C5 | 88.84 (8) |
| | | |
C8—C1—C2—C3 | 4.4 (4) | C13—C11—O2—Pd1 | 173.76 (13) |
Pd1—C1—C2—C3 | −98.2 (2) | C11—O2—Pd1—O1 | 7.48 (17) |
C8—C1—C2—Pd1 | 102.6 (2) | C11—O2—Pd1—C2 | −81.9 (3) |
C1—C2—C3—C4 | 38.5 (3) | C11—O2—Pd1—C6 | 169.93 (17) |
Pd1—C2—C3—C4 | −41.8 (2) | C11—O2—Pd1—C1 | 114.0 (3) |
C2—C3—C4—C5 | 38.2 (3) | C11—O2—Pd1—C5 | −153.30 (17) |
C3—C4—C5—C6 | −94.7 (3) | C9—O1—Pd1—O2 | −4.52 (16) |
C3—C4—C5—Pd1 | −14.3 (2) | C9—O1—Pd1—C2 | 156.36 (17) |
C4—C5—C6—C7 | 4.7 (4) | C9—O1—Pd1—C6 | −96.5 (3) |
Pd1—C5—C6—C7 | −97.5 (2) | C9—O1—Pd1—C1 | −166.88 (17) |
C4—C5—C6—Pd1 | 102.2 (2) | C9—O1—Pd1—C5 | 100.3 (3) |
C5—C6—C7—C8 | 38.1 (3) | C1—C2—Pd1—O2 | −171.75 (19) |
Pd1—C6—C7—C8 | −41.8 (2) | C3—C2—Pd1—O2 | −47.5 (3) |
C2—C1—C8—C7 | −94.5 (3) | C1—C2—Pd1—O1 | 97.86 (14) |
Pd1—C1—C8—C7 | −13.9 (2) | C3—C2—Pd1—O1 | −137.94 (16) |
C6—C7—C8—C1 | 38.1 (3) | C1—C2—Pd1—C6 | −65.22 (14) |
O1—C9—C10—C11 | 3.1 (4) | C3—C2—Pd1—C6 | 58.98 (17) |
C12—C9—C10—C11 | −178.3 (2) | C3—C2—Pd1—C1 | 124.2 (2) |
C9—C10—C11—O2 | 0.8 (4) | C1—C2—Pd1—C5 | −98.71 (14) |
C9—C10—C11—C13 | −179.9 (2) | C3—C2—Pd1—C5 | 25.49 (16) |
O1—C9—C12—F3 | −174.4 (2) | C5—C6—Pd1—O2 | 96.58 (13) |
C10—C9—C12—F3 | 6.8 (3) | C7—C6—Pd1—O2 | −139.15 (15) |
O1—C9—C12—F1 | −53.1 (3) | C5—C6—Pd1—O1 | −170.6 (2) |
C10—C9—C12—F1 | 128.0 (2) | C7—C6—Pd1—O1 | −46.4 (3) |
O1—C9—C12—F2 | 64.5 (3) | C5—C6—Pd1—C2 | −65.13 (14) |
C10—C9—C12—F2 | −114.4 (2) | C7—C6—Pd1—C2 | 59.14 (16) |
O2—C11—C13—F4B | 85.3 (14) | C5—C6—Pd1—C1 | −98.74 (14) |
C10—C11—C13—F4B | −94.1 (14) | C7—C6—Pd1—C1 | 25.53 (15) |
O2—C11—C13—F4C | 41.9 (10) | C7—C6—Pd1—C5 | 124.3 (2) |
C10—C11—C13—F4C | −137.4 (10) | C2—C1—Pd1—O2 | 171.5 (2) |
O2—C11—C13—F5 | −122.9 (3) | C8—C1—Pd1—O2 | 50.0 (3) |
C10—C11—C13—F5 | 57.8 (4) | C2—C1—Pd1—O1 | −81.88 (14) |
O2—C11—C13—F6 | 1.9 (3) | C8—C1—Pd1—O1 | 156.63 (15) |
C10—C11—C13—F6 | −177.4 (3) | C8—C1—Pd1—C2 | −121.5 (2) |
O2—C11—C13—F5C | −47.2 (16) | C2—C1—Pd1—C6 | 114.79 (14) |
C10—C11—C13—F5C | 133.4 (16) | C8—C1—Pd1—C6 | −6.70 (15) |
O2—C11—C13—F4 | 116.4 (2) | C2—C1—Pd1—C5 | 78.26 (14) |
C10—C11—C13—F4 | −62.9 (3) | C8—C1—Pd1—C5 | −43.23 (16) |
O2—C11—C13—F6B | 160.8 (13) | C6—C5—Pd1—O2 | −83.36 (13) |
C10—C11—C13—F6B | −18.6 (13) | C4—C5—Pd1—O2 | 155.39 (16) |
O2—C11—C13—F5B | −81.0 (13) | C6—C5—Pd1—O1 | 171.71 (19) |
C10—C11—C13—F5B | 99.6 (13) | C4—C5—Pd1—O1 | 50.5 (3) |
O2—C11—C13—F6C | −151.6 (11) | C6—C5—Pd1—C2 | 114.89 (14) |
C10—C11—C13—F6C | 29.0 (11) | C4—C5—Pd1—C2 | −6.36 (16) |
C10—C9—O1—Pd1 | 0.3 (3) | C4—C5—Pd1—C6 | −121.2 (2) |
C12—C9—O1—Pd1 | −178.37 (14) | C6—C5—Pd1—C1 | 78.24 (14) |
C10—C11—O2—Pd1 | −7.0 (3) | C4—C5—Pd1—C1 | −43.01 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···F06i | 0.99 | 2.74 | 3.448 (3) | 129 |
C1—H1···F04i | 1 | 2.48 | 3.312 (3) | 140 |
C2—H2···F4Bii | 1 | 2.38 | 3.078 (16) | 126 |
C2—H2···F4Cii | 1 | 2.58 | 3.429 (15) | 143 |
C3—H3A···F6Bii | 0.99 | 2.36 | 3.075 (14) | 129 |
C3—H3B···F2iii | 0.99 | 2.55 | 3.307 (3) | 133 |
C8—H8B···F04iii | 0.99 | 2.52 | 3.493 (3) | 167 |
C4—H4A···F6iv | 0.99 | 2.43 | 3.205 (4) | 134 |
C5—H5···F5Civ | 1 | 2.16 | 2.798 (15) | 120 |
C6—H6···F05iv | 1 | 2.54 | 3.481 (3) | 156 |
C7—H7A···F3v | 0.99 | 2.56 | 3.348 (3) | 136 |
C10—H10···F01vi | 0.95 | 2.35 | 3.289 (3) | 168 |
C10—H10···F3 | 0.95 | 2.34 | 2.711 (3) | 103 |
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y, −z+1; (v) x, y−1, z; (vi) −x, −y+1, −z+1. |
Experimental details
| (8Fth3) | (10rth5_0ma) | (9Tth12_L) | (10Rth7) |
Crystal data |
Chemical formula | C13H19O2Pd·F6P | C13H19O2Pd·BF4 | C16H16F3O2PdS·F6P | C16H16F3O2PdS·BF4 |
Mr | 458.65 | 400.49 | 580.72 | 522.56 |
Crystal system, space group | Monoclinic, P21/c | Orthorhombic, Pca21 | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 100 | 100 | 100 | 100 |
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), 90 | 90, 90, 90 | 90, 124.439 (1), 90 | 90, 125.684 (2), 90 |
V (Å3) | 1589.49 (15) | 1465.90 (10) | 1910.15 (7) | 1787.35 (9) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 1.34 | 1.31 | 1.26 | 1.24 |
Crystal size (mm) | 0.13 × 0.07 × 0.03 | 0.34 × 0.1 × 0.07 | 0.35 × 0.2 × 0.1 | 0.28 × 0.16 × 0.11 |
|
Data collection |
Diffractometer | Bruker 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 correction | Multi-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, Tmax | 0.846, 0.961 | 0.664, 0.914 | 0.667, 0.884 | 0.724, 0.876 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10747, 3952, 3112 | 15654, 3117, 2960 | 15058, 4606, 3596 | 21884, 4464, 3873 |
Rint | 0.041 | 0.025 | 0.024 | 0.033 |
(sin θ/λ)max (Å−1) | 0.667 | 0.669 | 0.661 | 0.669 |
|
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 reflections | 3952 | 3117 | 4606 | 4464 |
No. of parameters | 210 | 192 | 271 | 253 |
No. of restraints | 0 | 1 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.67 | 1.05, −0.61 | 1.15, −0.71 | 0.61, −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 formula | C13H13F6O2Pd·F6P |
Mr | 566.6 |
Crystal system, space group | Monoclinic, 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 |
V (Å3) | 1768.91 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.27 |
Crystal size (mm) | 0.38 × 0.22 × 0.07 |
|
Data collection |
Diffractometer | Bruker APEX-II 4K Kappa CCD diffractometer |
Absorption correction | Multi-scan SADABS (Bruker, 2004) |
Tmin, Tmax | 0.644, 0.916 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16999, 4248, 3805 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.661 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.062, 1.07 |
No. of reflections | 4248 |
No. of parameters | 295 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.60, −0.65 |
Absolute structure | ? |
Absolute structure parameter | ? |
Hydrogen-bond geometry (Å, º) for (8Fth3) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···F6 | 0.95 | 2.39 | 3.295 (4) | 158.7 |
C7—H7A···F4i | 0.99 | 2.47 | 3.311 (4) | 143.1 |
C2—H2···F6ii | 1 | 2.52 | 3.366 (4) | 141.9 |
C2—H2···F3ii | 1 | 2.54 | 3.257 (4) | 128.9 |
C5—H5···F3iii | 1 | 2.36 | 3.142 (4) | 134.9 |
C8—H8A···F1iv | 0.99 | 2.53 | 3.481 (4) | 160.6 |
C6—H6···F1v | 1 | 2.45 | 3.242 (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···A | D—H | H···A | D···A | D—H···A |
C7—H7B···F01 | 0.99 | 2.38 | 3.209 (5) | 141.2 |
C2—H2···F02i | 1 | 2.52 | 3.222 (4) | 126.7 |
C6—H6···F04ii | 1 | 2.26 | 3.137 (4) | 145.8 |
C12—H12B···F04iii | 0.98 | 2.53 | 3.497 (3) | 169.2 |
C10—H10···F03iii | 0.95 | 2.42 | 3.320 (4) | 158.9 |
C13—H13B···F03iii | 0.98 | 2.53 | 3.435 (4) | 153.2 |
Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+1, −y+2, z−1/2; (iii) x+1/2, −y+2, z. |
Hydrogen-bond geometry (Å, º) for (9Tth12_L) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···F2 | 0.95 | 2.33 | 2.712 (3) | 103.6 |
C14—H14···F01i | 0.95 | 2.32 | 3.193 (3) | 152.3 |
C5—H5···F01ii | 1 | 2.47 | 3.274 (3) | 137 |
C6—H6···F06iii | 1 | 2.48 | 3.175 (3) | 126 |
C15—H15···F03iv | 0.95 | 2.33 | 3.022 (3) | 128.9 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x−1, y, z−1; (iv) −x+1, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) for (10Rth7) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···F01 | 0.95 | 2.51 | 3.420 (3) | 161.5 |
C10—H10···F3 | 0.95 | 2.35 | 2.731 (2) | 103.3 |
C14—H14···F01 | 0.95 | 2.5 | 3.351 (3) | 149.4 |
C14—H14···F04 | 0.95 | 2.46 | 3.349 (3) | 155.2 |
C2—H2···F01i | 1 | 2.5 | 3.278 (3) | 134.6 |
C3—H3B···F03i | 0.99 | 2.51 | 3.496 (3) | 177 |
C5—H5···F04ii | 1 | 2.39 | 3.106 (3) | 127.8 |
C6—H6···F04iii | 1 | 2.29 | 3.290 (3) | 173.9 |
C16—H16···F01iv | 0.95 | 2.48 | 3.165 (3) | 128.5 |
C16—H16···F02iv | 0.95 | 2.55 | 3.262 (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, z−1/2. |
Hydrogen-bond geometry (Å, º) for (10ath3_0m) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···F06i | 0.99 | 2.74 | 3.448 (3) | 128.7 |
C1—H1···F04i | 1 | 2.48 | 3.312 (3) | 140.2 |
C2—H2···F4Bii | 1 | 2.38 | 3.078 (16) | 125.8 |
C2—H2···F4Cii | 1 | 2.58 | 3.429 (15) | 143 |
C3—H3A···F6Bii | 0.99 | 2.36 | 3.075 (14) | 128.7 |
C3—H3B···F2iii | 0.99 | 2.55 | 3.307 (3) | 133.2 |
C8—H8B···F04iii | 0.99 | 2.52 | 3.493 (3) | 166.5 |
C4—H4A···F6iv | 0.99 | 2.43 | 3.205 (4) | 134.4 |
C5—H5···F5Civ | 1 | 2.16 | 2.798 (15) | 120.2 |
C6—H6···F05iv | 1 | 2.54 | 3.481 (3) | 155.8 |
C7—H7A···F3v | 0.99 | 2.56 | 3.348 (3) | 136.3 |
C10—H10···F01vi | 0.95 | 2.35 | 3.289 (3) | 168.4 |
C10—H10···F3 | 0.95 | 2.34 | 2.711 (3) | 102.8 |
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y, −z+1; (v) x, y−1, z; (vi) −x, −y+1, −z+1. |