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Reaction of the Pd complex [(3,5-Me2pz-CO-furan)2PdCl2] (where pzH is pyrazole) and the Lewis acid B(C6F5)3 in the presence of adventitious water resulted in the formation of the title compound, [PdCl2(C10H10N2O2)2]·2C18HBF15O2·2H2O·2CH2Cl2, in 60% yield. The Pd complex occupies a crystallographic inversion center and exhibits a square-planar geometry. The two proposed dichloromethane molecules in the formula are highly disordered.
Supporting information
CCDC reference: 282360
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
Some non-H atoms missing
- R factor = 0.030
- wR factor = 0.085
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level A
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
calculated from the _atom_site* data lies outside
the range 0.90 <> 1.10
From the CIF: _cell_formula_units_Z 1
From the CIF: _chemical_formula_weight 1823.60
TEST: Calculate formula weight from _atom_site_*
atom mass num sum
C 12.01 56.00 672.62
H 1.01 28.00 28.22
N 14.01 4.00 56.03
O 16.00 8.00 127.99
F 19.00 30.00 569.94
Pd 106.42 1.00 106.42
Cl 35.45 2.00 70.91
B 10.81 2.00 21.62
Calculated formula weight 1653.75
| Author Response: see _exptl_special_details
|
PLAT043_ALERT_1_A Check Reported Molecular Weight ................ 1823.60
| Author Response: see _exptl_special_details
|
PLAT044_ALERT_1_A Calculated and Reported Dx Differ .............. ?
| Author Response: see _exptl_special_details
|
PLAT051_ALERT_1_A Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 24.82 Perc.
| Author Response: see _exptl_special_details
|
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 281.00 A 3
| Author Response: see _exptl_special_details
|
Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor O4 - H6 ... ?
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O3
PLAT432_ALERT_2_C Short Inter X...Y Contact F10 .. C15 .. 2.96 Ang.
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C58 H32 B2 Cl6 F30 N4 O8 Pd
Atom count from _chemical_formula_moiety:C58 H32 B2 Cl6 F30 N4 O6.4
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C58 H32 B2 Cl6 F30 N4 O8 Pd1
Atom count from the _atom_site data: C56 H28 B2 Cl2 F30 N4 O8 Pd1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
symmetry error - see SYMMG tests
From the CIF: _cell_formula_units_Z 1
From the CIF: _chemical_formula_sum C58 H32 B2 Cl6 F30 N4 O8 Pd
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 58.00 56.00 2.00
H 32.00 28.00 4.00
B 2.00 2.00 0.00
Cl 6.00 2.00 4.00
F 30.00 30.00 0.00
N 4.00 4.00 0.00
O 8.00 8.00 0.00
Pd 1.00 1.00 0.00
5 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Dichlorobis[2-(3,5-dimethylpyrazolyl-1-carbonyl)furan]palladium(II)
bis[tris(pentafluorophenyl)borane] tetrahydrate dichloromethane disolvate
top
Crystal data top
[PdCl2(C10H10N2O2)2]·2C18HBF15O2·2H2O·2CH2Cl2 | Z = 1 |
Mr = 1823.60 | F(000) = 900 |
Triclinic, P1 | Dx = 1.758 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4595 (4) Å | Cell parameters from 9311 reflections |
b = 12.5105 (5) Å | θ = 2.0–26.4° |
c = 13.6969 (6) Å | µ = 0.64 mm−1 |
α = 81.169 (1)° | T = 173 K |
β = 77.571 (1)° | Block, red |
γ = 83.037 (1)° | 0.40 × 0.30 × 0.20 mm |
V = 1722.30 (12) Å3 | |
Data collection top
Bruker SMART 1000 CCD diffractometer | 6976 independent reflections |
Radiation source: fine-focus sealed tube | 6381 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
0.30° ω scans | θmax = 26.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −13→13 |
Tmin = 0.78, Tmax = 0.88 | k = −15→15 |
14381 measured reflections | l = −17→17 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0517P)2 + 0.5736P] where P = (Fo2 + 2Fc2)/3 |
6976 reflections | (Δ/σ)max = 0.001 |
482 parameters | Δρmax = 0.55 e Å−3 |
3 restraints | Δρmin = −0.46 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Pd | 1.0000 | 0.0000 | 1.0000 | 0.02140 (7) | |
Cl1 | 1.14956 (5) | −0.10376 (4) | 0.89546 (4) | 0.03960 (13) | |
F1 | 0.61809 (11) | 0.85145 (10) | 0.59238 (9) | 0.0355 (3) | |
F2 | 0.87487 (12) | 0.80380 (10) | 0.58578 (10) | 0.0408 (3) | |
F3 | 1.01447 (11) | 0.65624 (11) | 0.46873 (10) | 0.0424 (3) | |
F4 | 0.89078 (11) | 0.55757 (10) | 0.35543 (9) | 0.0389 (3) | |
F5 | 0.63553 (11) | 0.60116 (9) | 0.36175 (8) | 0.0299 (2) | |
F6 | 0.50756 (13) | 0.86260 (9) | 0.27900 (8) | 0.0370 (3) | |
F7 | 0.42701 (16) | 0.81019 (11) | 0.12263 (9) | 0.0494 (3) | |
F8 | 0.27352 (14) | 0.64282 (11) | 0.14788 (10) | 0.0459 (3) | |
F9 | 0.20637 (12) | 0.52734 (9) | 0.33389 (9) | 0.0358 (3) | |
F10 | 0.28729 (11) | 0.57741 (8) | 0.49109 (8) | 0.0297 (2) | |
F11 | 0.18364 (11) | 0.83779 (10) | 0.57006 (9) | 0.0354 (3) | |
F12 | 0.03565 (12) | 0.76571 (12) | 0.74547 (9) | 0.0438 (3) | |
F13 | 0.13541 (12) | 0.60353 (11) | 0.87413 (9) | 0.0413 (3) | |
F14 | 0.38694 (12) | 0.51574 (9) | 0.82022 (9) | 0.0357 (3) | |
F15 | 0.53605 (11) | 0.58536 (9) | 0.64587 (9) | 0.0322 (2) | |
O1 | 1.13258 (14) | 0.08766 (12) | 0.68065 (10) | 0.0338 (3) | |
O2 | 1.20744 (15) | 0.22102 (13) | 0.79534 (11) | 0.0390 (3) | |
O3 | 0.42862 (13) | 0.88735 (10) | 0.47445 (10) | 0.0242 (3) | |
H3 | 0.4919 | 0.9146 | 0.4334 | 0.036* | |
H4 | 0.410 (3) | 0.914 (2) | 0.5272 (15) | 0.052 (8)* | |
N1 | 0.88905 (15) | 0.02739 (13) | 0.89307 (11) | 0.0272 (3) | |
N2 | 0.94155 (15) | 0.05758 (13) | 0.79231 (11) | 0.0268 (3) | |
B1 | 0.45400 (19) | 0.75972 (15) | 0.48673 (15) | 0.0220 (4) | |
C1 | 0.6967 (2) | −0.0663 (2) | 0.99028 (17) | 0.0429 (5) | |
H1A | 0.7390 | −0.0634 | 1.0470 | 0.064* | |
H1B | 0.6855 | −0.1420 | 0.9860 | 0.064* | |
H1C | 0.6104 | −0.0244 | 1.0007 | 0.064* | |
C2 | 0.78051 (19) | −0.01896 (16) | 0.89454 (15) | 0.0316 (4) | |
C3 | 0.7615 (2) | −0.01661 (17) | 0.79593 (16) | 0.0339 (4) | |
H3A | 0.6898 | −0.0425 | 0.7770 | 0.041* | |
C4 | 0.8647 (2) | 0.02969 (16) | 0.73243 (15) | 0.0304 (4) | |
C5 | 0.8931 (2) | 0.05424 (19) | 0.62052 (15) | 0.0382 (5) | |
H5A | 0.9084 | 0.1310 | 0.6009 | 0.057* | |
H5B | 0.8180 | 0.0389 | 0.5943 | 0.057* | |
H5C | 0.9716 | 0.0089 | 0.5926 | 0.057* | |
C6 | 1.06126 (18) | 0.10804 (16) | 0.75888 (14) | 0.0287 (4) | |
C7 | 1.0831 (2) | 0.18808 (17) | 0.81821 (14) | 0.0316 (4) | |
C8 | 1.0038 (2) | 0.24743 (17) | 0.88715 (15) | 0.0360 (4) | |
H8 | 0.9133 | 0.2411 | 0.9150 | 0.043* | |
C9 | 1.0842 (3) | 0.32051 (18) | 0.90866 (18) | 0.0442 (5) | |
H9 | 1.0581 | 0.3729 | 0.9543 | 0.053* | |
C10 | 1.2041 (3) | 0.3015 (2) | 0.85224 (18) | 0.0467 (6) | |
H10 | 1.2775 | 0.3395 | 0.8521 | 0.056* | |
C11 | 0.61241 (17) | 0.72983 (13) | 0.47676 (13) | 0.0226 (3) | |
C12 | 0.68214 (18) | 0.77738 (14) | 0.53192 (14) | 0.0260 (4) | |
C13 | 0.81480 (19) | 0.75393 (15) | 0.53087 (15) | 0.0293 (4) | |
C14 | 0.88543 (18) | 0.67907 (16) | 0.47174 (15) | 0.0299 (4) | |
C15 | 0.82251 (18) | 0.62977 (15) | 0.41454 (14) | 0.0280 (4) | |
C16 | 0.68942 (18) | 0.65533 (14) | 0.41864 (13) | 0.0239 (3) | |
C17 | 0.39806 (17) | 0.72505 (14) | 0.39416 (13) | 0.0231 (3) | |
C18 | 0.4297 (2) | 0.77974 (15) | 0.29720 (14) | 0.0289 (4) | |
C19 | 0.3899 (2) | 0.75424 (16) | 0.21460 (15) | 0.0340 (4) | |
C20 | 0.3132 (2) | 0.66917 (16) | 0.22744 (15) | 0.0329 (4) | |
C21 | 0.27836 (18) | 0.61134 (15) | 0.32144 (15) | 0.0281 (4) | |
C22 | 0.32167 (17) | 0.63975 (14) | 0.40225 (13) | 0.0244 (3) | |
C23 | 0.36871 (17) | 0.71764 (14) | 0.59810 (13) | 0.0230 (3) | |
C24 | 0.23955 (18) | 0.75848 (15) | 0.63024 (14) | 0.0266 (4) | |
C25 | 0.15993 (18) | 0.72292 (17) | 0.72092 (14) | 0.0304 (4) | |
C26 | 0.2104 (2) | 0.64077 (17) | 0.78540 (14) | 0.0308 (4) | |
C27 | 0.33767 (19) | 0.59684 (14) | 0.75798 (14) | 0.0275 (4) | |
C28 | 0.41398 (17) | 0.63495 (14) | 0.66664 (14) | 0.0238 (3) | |
O4 | 0.38529 (14) | 0.98760 (11) | 0.63258 (11) | 0.0314 (3) | |
H5 | 0.3129 (19) | 1.021 (2) | 0.646 (2) | 0.054 (8)* | |
H6 | 0.411 (3) | 0.955 (2) | 0.6825 (17) | 0.059 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd | 0.02255 (11) | 0.02534 (11) | 0.01549 (10) | −0.00589 (7) | −0.00042 (7) | −0.00200 (7) |
Cl1 | 0.0419 (3) | 0.0388 (3) | 0.0323 (3) | −0.0001 (2) | 0.0075 (2) | −0.0109 (2) |
F1 | 0.0331 (6) | 0.0387 (6) | 0.0414 (7) | 0.0020 (5) | −0.0135 (5) | −0.0218 (5) |
F2 | 0.0335 (6) | 0.0456 (7) | 0.0515 (8) | −0.0089 (5) | −0.0179 (6) | −0.0144 (6) |
F3 | 0.0212 (6) | 0.0515 (8) | 0.0538 (8) | −0.0033 (5) | −0.0046 (5) | −0.0092 (6) |
F4 | 0.0306 (6) | 0.0419 (7) | 0.0406 (7) | 0.0035 (5) | 0.0034 (5) | −0.0144 (5) |
F5 | 0.0310 (6) | 0.0291 (5) | 0.0318 (6) | −0.0021 (4) | −0.0057 (5) | −0.0126 (4) |
F6 | 0.0535 (7) | 0.0342 (6) | 0.0249 (6) | −0.0195 (5) | −0.0033 (5) | −0.0030 (5) |
F7 | 0.0869 (10) | 0.0435 (7) | 0.0206 (6) | −0.0174 (7) | −0.0118 (6) | −0.0021 (5) |
F8 | 0.0643 (9) | 0.0476 (7) | 0.0360 (7) | −0.0060 (6) | −0.0238 (6) | −0.0169 (6) |
F9 | 0.0348 (6) | 0.0348 (6) | 0.0439 (7) | −0.0091 (5) | −0.0103 (5) | −0.0160 (5) |
F10 | 0.0366 (6) | 0.0253 (5) | 0.0285 (6) | −0.0103 (4) | −0.0057 (5) | −0.0034 (4) |
F11 | 0.0279 (6) | 0.0467 (7) | 0.0280 (6) | 0.0063 (5) | −0.0076 (4) | 0.0016 (5) |
F12 | 0.0255 (6) | 0.0681 (9) | 0.0328 (6) | 0.0039 (6) | −0.0001 (5) | −0.0062 (6) |
F13 | 0.0413 (7) | 0.0514 (7) | 0.0257 (6) | −0.0120 (6) | 0.0043 (5) | 0.0020 (5) |
F14 | 0.0446 (7) | 0.0287 (6) | 0.0309 (6) | −0.0048 (5) | −0.0075 (5) | 0.0062 (5) |
F15 | 0.0296 (6) | 0.0258 (5) | 0.0360 (6) | 0.0022 (4) | −0.0024 (5) | 0.0026 (4) |
O1 | 0.0328 (7) | 0.0463 (8) | 0.0197 (6) | −0.0078 (6) | −0.0012 (5) | 0.0012 (6) |
O2 | 0.0378 (8) | 0.0502 (9) | 0.0298 (7) | −0.0233 (7) | −0.0038 (6) | 0.0033 (6) |
O3 | 0.0303 (7) | 0.0202 (6) | 0.0231 (6) | −0.0028 (5) | −0.0055 (5) | −0.0053 (5) |
N1 | 0.0268 (8) | 0.0345 (8) | 0.0190 (7) | −0.0100 (6) | −0.0015 (6) | 0.0021 (6) |
N2 | 0.0294 (8) | 0.0317 (8) | 0.0192 (7) | −0.0087 (6) | −0.0041 (6) | 0.0008 (6) |
B1 | 0.0256 (10) | 0.0182 (9) | 0.0231 (9) | −0.0027 (7) | −0.0053 (7) | −0.0050 (7) |
C1 | 0.0335 (11) | 0.0576 (14) | 0.0364 (11) | −0.0218 (10) | −0.0061 (9) | 0.0104 (10) |
C2 | 0.0285 (9) | 0.0353 (10) | 0.0308 (10) | −0.0109 (8) | −0.0060 (8) | 0.0024 (8) |
C3 | 0.0342 (10) | 0.0360 (10) | 0.0346 (10) | −0.0120 (8) | −0.0144 (8) | 0.0036 (8) |
C4 | 0.0348 (10) | 0.0307 (9) | 0.0284 (10) | −0.0069 (8) | −0.0130 (8) | 0.0003 (8) |
C5 | 0.0470 (12) | 0.0452 (12) | 0.0258 (10) | −0.0112 (10) | −0.0151 (9) | 0.0020 (9) |
C6 | 0.0290 (9) | 0.0343 (10) | 0.0213 (9) | −0.0085 (8) | −0.0053 (7) | 0.0055 (7) |
C7 | 0.0337 (10) | 0.0369 (10) | 0.0239 (9) | −0.0154 (8) | −0.0058 (7) | 0.0056 (8) |
C8 | 0.0418 (11) | 0.0341 (10) | 0.0302 (10) | −0.0088 (9) | −0.0050 (8) | 0.0022 (8) |
C9 | 0.0626 (15) | 0.0341 (11) | 0.0377 (12) | −0.0155 (10) | −0.0096 (11) | −0.0021 (9) |
C10 | 0.0617 (15) | 0.0462 (13) | 0.0376 (12) | −0.0305 (11) | −0.0144 (11) | 0.0042 (10) |
C11 | 0.0252 (9) | 0.0208 (8) | 0.0206 (8) | −0.0053 (7) | −0.0022 (6) | 0.0001 (6) |
C12 | 0.0285 (9) | 0.0238 (8) | 0.0259 (9) | −0.0033 (7) | −0.0052 (7) | −0.0040 (7) |
C13 | 0.0292 (9) | 0.0296 (9) | 0.0307 (10) | −0.0102 (8) | −0.0072 (8) | −0.0014 (7) |
C14 | 0.0211 (9) | 0.0327 (10) | 0.0327 (10) | −0.0057 (7) | −0.0014 (7) | 0.0024 (8) |
C15 | 0.0274 (9) | 0.0263 (9) | 0.0264 (9) | −0.0033 (7) | 0.0027 (7) | −0.0019 (7) |
C16 | 0.0275 (9) | 0.0215 (8) | 0.0219 (8) | −0.0069 (7) | −0.0023 (7) | −0.0010 (6) |
C17 | 0.0249 (8) | 0.0209 (8) | 0.0241 (9) | 0.0002 (7) | −0.0060 (7) | −0.0057 (7) |
C18 | 0.0364 (10) | 0.0249 (9) | 0.0268 (9) | −0.0050 (8) | −0.0061 (8) | −0.0061 (7) |
C19 | 0.0510 (12) | 0.0286 (9) | 0.0232 (9) | −0.0027 (9) | −0.0086 (8) | −0.0053 (7) |
C20 | 0.0402 (11) | 0.0345 (10) | 0.0292 (10) | 0.0027 (8) | −0.0147 (8) | −0.0138 (8) |
C21 | 0.0249 (9) | 0.0256 (9) | 0.0375 (10) | −0.0002 (7) | −0.0092 (8) | −0.0132 (8) |
C22 | 0.0245 (8) | 0.0235 (8) | 0.0250 (9) | 0.0007 (7) | −0.0049 (7) | −0.0051 (7) |
C23 | 0.0265 (9) | 0.0230 (8) | 0.0217 (8) | −0.0053 (7) | −0.0058 (7) | −0.0059 (7) |
C24 | 0.0276 (9) | 0.0310 (9) | 0.0228 (9) | −0.0014 (7) | −0.0083 (7) | −0.0049 (7) |
C25 | 0.0246 (9) | 0.0420 (11) | 0.0255 (9) | −0.0035 (8) | −0.0037 (7) | −0.0088 (8) |
C26 | 0.0331 (10) | 0.0372 (10) | 0.0221 (9) | −0.0119 (8) | −0.0003 (7) | −0.0041 (8) |
C27 | 0.0361 (10) | 0.0230 (8) | 0.0250 (9) | −0.0068 (7) | −0.0083 (8) | −0.0016 (7) |
C28 | 0.0255 (9) | 0.0207 (8) | 0.0262 (9) | −0.0040 (7) | −0.0049 (7) | −0.0055 (7) |
O4 | 0.0327 (8) | 0.0295 (7) | 0.0342 (8) | −0.0003 (6) | −0.0078 (6) | −0.0113 (6) |
Geometric parameters (Å, º) top
Pd—N1i | 2.0225 (15) | C1—H1C | 0.9800 |
Pd—N1 | 2.0225 (15) | C2—C3 | 1.403 (3) |
Pd—Cl1i | 2.3014 (5) | C3—C4 | 1.360 (3) |
Pd—Cl1 | 2.3014 (5) | C3—H3A | 0.9500 |
F1—C12 | 1.356 (2) | C4—C5 | 1.488 (3) |
F2—C13 | 1.339 (2) | C5—H5A | 0.9800 |
F3—C14 | 1.338 (2) | C5—H5B | 0.9800 |
F4—C15 | 1.342 (2) | C5—H5C | 0.9800 |
F5—C16 | 1.352 (2) | C6—C7 | 1.449 (3) |
F6—C18 | 1.356 (2) | C7—C8 | 1.364 (3) |
F7—C19 | 1.346 (2) | C8—C9 | 1.416 (3) |
F8—C20 | 1.344 (2) | C8—H8 | 0.9500 |
F9—C21 | 1.335 (2) | C9—C10 | 1.339 (4) |
F10—C22 | 1.344 (2) | C9—H9 | 0.9500 |
F11—C24 | 1.350 (2) | C10—H10 | 0.9500 |
F12—C25 | 1.337 (2) | C11—C16 | 1.386 (3) |
F13—C26 | 1.347 (2) | C11—C12 | 1.392 (3) |
F14—C27 | 1.349 (2) | C12—C13 | 1.380 (3) |
F15—C28 | 1.342 (2) | C13—C14 | 1.373 (3) |
O1—C6 | 1.210 (2) | C14—C15 | 1.377 (3) |
O2—C10 | 1.358 (3) | C15—C16 | 1.381 (3) |
O2—C7 | 1.369 (2) | C17—C22 | 1.386 (3) |
O3—B1 | 1.576 (2) | C17—C18 | 1.389 (3) |
O3—H3 | 0.8400 | C18—C19 | 1.379 (3) |
O3—H4 | 0.820 (16) | C19—C20 | 1.377 (3) |
N1—C2 | 1.331 (2) | C20—C21 | 1.375 (3) |
N1—N2 | 1.383 (2) | C21—C22 | 1.390 (3) |
N2—C4 | 1.371 (2) | C23—C24 | 1.388 (3) |
N2—C6 | 1.425 (2) | C23—C28 | 1.396 (2) |
B1—C11 | 1.635 (3) | C24—C25 | 1.382 (3) |
B1—C23 | 1.638 (3) | C25—C26 | 1.380 (3) |
B1—C17 | 1.639 (2) | C26—C27 | 1.374 (3) |
C1—C2 | 1.494 (3) | C27—C28 | 1.382 (3) |
C1—H1A | 0.9800 | O4—H5 | 0.820 (16) |
C1—H1B | 0.9800 | O4—H6 | 0.820 (16) |
| | | |
N1i—Pd—N1 | 180.0 | O2—C10—H10 | 124.3 |
N1i—Pd—Cl1i | 87.96 (5) | C16—C11—C12 | 113.45 (16) |
N1—Pd—Cl1i | 92.04 (5) | C16—C11—B1 | 125.82 (15) |
N1i—Pd—Cl1 | 92.04 (5) | C12—C11—B1 | 120.70 (15) |
N1—Pd—Cl1 | 87.96 (5) | F1—C12—C13 | 116.10 (16) |
Cl1i—Pd—Cl1 | 180.0 | F1—C12—C11 | 119.38 (16) |
C10—O2—C7 | 105.73 (18) | C13—C12—C11 | 124.52 (17) |
B1—O3—H3 | 109.5 | F2—C13—C14 | 120.04 (17) |
B1—O3—H4 | 115.6 (19) | F2—C13—C12 | 120.86 (17) |
H3—O3—H4 | 112.7 | C14—C13—C12 | 119.10 (17) |
C2—N1—N2 | 105.67 (15) | F3—C14—C13 | 119.99 (17) |
C2—N1—Pd | 126.68 (13) | F3—C14—C15 | 120.72 (18) |
N2—N1—Pd | 122.36 (11) | C13—C14—C15 | 119.28 (17) |
C4—N2—N1 | 110.59 (15) | F4—C15—C14 | 119.85 (17) |
C4—N2—C6 | 126.49 (16) | F4—C15—C16 | 120.64 (17) |
N1—N2—C6 | 122.90 (15) | C14—C15—C16 | 119.51 (17) |
O3—B1—C11 | 107.10 (13) | F5—C16—C15 | 115.35 (16) |
O3—B1—C23 | 105.36 (13) | F5—C16—C11 | 120.51 (16) |
C11—B1—C23 | 113.36 (14) | C15—C16—C11 | 124.14 (17) |
O3—B1—C17 | 104.09 (13) | C22—C17—C18 | 114.08 (16) |
C11—B1—C17 | 113.02 (14) | C22—C17—B1 | 125.26 (16) |
C23—B1—C17 | 112.96 (14) | C18—C17—B1 | 120.62 (15) |
C2—C1—H1A | 109.5 | F6—C18—C19 | 115.87 (17) |
C2—C1—H1B | 109.5 | F6—C18—C17 | 119.64 (16) |
H1A—C1—H1B | 109.5 | C19—C18—C17 | 124.47 (18) |
C2—C1—H1C | 109.5 | F7—C19—C20 | 120.45 (17) |
H1A—C1—H1C | 109.5 | F7—C19—C18 | 120.72 (18) |
H1B—C1—H1C | 109.5 | C20—C19—C18 | 118.82 (18) |
N1—C2—C3 | 110.09 (17) | F8—C20—C21 | 120.43 (18) |
N1—C2—C1 | 122.41 (18) | F8—C20—C19 | 119.78 (19) |
C3—C2—C1 | 127.50 (18) | C21—C20—C19 | 119.78 (17) |
C4—C3—C2 | 107.26 (17) | F9—C21—C20 | 120.01 (17) |
C4—C3—H3A | 126.4 | F9—C21—C22 | 120.73 (18) |
C2—C3—H3A | 126.4 | C20—C21—C22 | 119.24 (17) |
C3—C4—N2 | 106.35 (17) | F10—C22—C17 | 120.52 (15) |
C3—C4—C5 | 130.11 (18) | F10—C22—C21 | 115.87 (16) |
N2—C4—C5 | 123.46 (17) | C17—C22—C21 | 123.60 (17) |
C4—C5—H5A | 109.5 | C24—C23—C28 | 113.75 (16) |
C4—C5—H5B | 109.5 | C24—C23—B1 | 121.72 (15) |
H5A—C5—H5B | 109.5 | C28—C23—B1 | 124.43 (16) |
C4—C5—H5C | 109.5 | F11—C24—C25 | 115.74 (16) |
H5A—C5—H5C | 109.5 | F11—C24—C23 | 119.49 (16) |
H5B—C5—H5C | 109.5 | C25—C24—C23 | 124.76 (17) |
O1—C6—N2 | 118.93 (17) | F12—C25—C26 | 120.34 (17) |
O1—C6—C7 | 124.41 (18) | F12—C25—C24 | 120.92 (18) |
N2—C6—C7 | 116.45 (16) | C26—C25—C24 | 118.73 (17) |
C8—C7—O2 | 110.32 (18) | F13—C26—C27 | 120.23 (18) |
C8—C7—C6 | 134.30 (19) | F13—C26—C25 | 120.41 (18) |
O2—C7—C6 | 115.04 (18) | C27—C26—C25 | 119.37 (17) |
C7—C8—C9 | 105.9 (2) | F14—C27—C26 | 119.59 (17) |
C7—C8—H8 | 127.1 | F14—C27—C28 | 120.39 (17) |
C9—C8—H8 | 127.1 | C26—C27—C28 | 120.02 (17) |
C10—C9—C8 | 106.7 (2) | F15—C28—C27 | 115.51 (16) |
C10—C9—H9 | 126.7 | F15—C28—C23 | 121.10 (16) |
C8—C9—H9 | 126.7 | C27—C28—C23 | 123.37 (17) |
C9—C10—O2 | 111.4 (2) | H5—O4—H6 | 113 (3) |
C9—C10—H10 | 124.3 | | |
| | | |
Cl1i—Pd—N1—C2 | −76.61 (17) | C12—C11—C16—C15 | −0.2 (3) |
Cl1—Pd—N1—C2 | 103.39 (17) | B1—C11—C16—C15 | −177.91 (16) |
Cl1i—Pd—N1—N2 | 132.85 (13) | O3—B1—C17—C22 | −136.10 (17) |
Cl1—Pd—N1—N2 | −47.15 (13) | C11—B1—C17—C22 | 108.04 (19) |
C2—N1—N2—C4 | 0.1 (2) | C23—B1—C17—C22 | −22.3 (2) |
Pd—N1—N2—C4 | 155.90 (13) | O3—B1—C17—C18 | 46.3 (2) |
C2—N1—N2—C6 | −178.41 (17) | C11—B1—C17—C18 | −69.6 (2) |
Pd—N1—N2—C6 | −22.6 (2) | C23—B1—C17—C18 | 160.04 (16) |
N2—N1—C2—C3 | −1.3 (2) | C22—C17—C18—F6 | −177.90 (16) |
Pd—N1—C2—C3 | −155.72 (14) | B1—C17—C18—F6 | 0.0 (3) |
N2—N1—C2—C1 | 178.02 (19) | C22—C17—C18—C19 | 0.4 (3) |
Pd—N1—C2—C1 | 23.6 (3) | B1—C17—C18—C19 | 178.24 (18) |
N1—C2—C3—C4 | 2.0 (2) | F6—C18—C19—F7 | −0.4 (3) |
C1—C2—C3—C4 | −177.2 (2) | C17—C18—C19—F7 | −178.74 (18) |
C2—C3—C4—N2 | −1.9 (2) | F6—C18—C19—C20 | 178.48 (18) |
C2—C3—C4—C5 | −178.7 (2) | C17—C18—C19—C20 | 0.1 (3) |
N1—N2—C4—C3 | 1.2 (2) | F7—C19—C20—F8 | −1.0 (3) |
C6—N2—C4—C3 | 179.59 (18) | C18—C19—C20—F8 | −179.86 (18) |
N1—N2—C4—C5 | 178.20 (18) | F7—C19—C20—C21 | 178.63 (18) |
C6—N2—C4—C5 | −3.4 (3) | C18—C19—C20—C21 | −0.3 (3) |
C4—N2—C6—O1 | −32.7 (3) | F8—C20—C21—F9 | 1.0 (3) |
N1—N2—C6—O1 | 145.51 (18) | C19—C20—C21—F9 | −178.57 (18) |
C4—N2—C6—C7 | 142.24 (19) | F8—C20—C21—C22 | 179.45 (17) |
N1—N2—C6—C7 | −39.5 (2) | C19—C20—C21—C22 | −0.1 (3) |
C10—O2—C7—C8 | 0.5 (2) | C18—C17—C22—F10 | 177.80 (16) |
C10—O2—C7—C6 | 174.90 (17) | B1—C17—C22—F10 | 0.0 (3) |
O1—C6—C7—C8 | 156.3 (2) | C18—C17—C22—C21 | −0.8 (3) |
N2—C6—C7—C8 | −18.3 (3) | B1—C17—C22—C21 | −178.56 (16) |
O1—C6—C7—O2 | −16.3 (3) | F9—C21—C22—F10 | 0.5 (2) |
N2—C6—C7—O2 | 169.06 (16) | C20—C21—C22—F10 | −177.94 (16) |
O2—C7—C8—C9 | −0.5 (2) | F9—C21—C22—C17 | 179.14 (16) |
C6—C7—C8—C9 | −173.4 (2) | C20—C21—C22—C17 | 0.7 (3) |
C7—C8—C9—C10 | 0.3 (2) | O3—B1—C23—C24 | 46.0 (2) |
C8—C9—C10—O2 | 0.0 (3) | C11—B1—C23—C24 | 162.80 (15) |
C7—O2—C10—C9 | −0.3 (3) | C17—B1—C23—C24 | −67.0 (2) |
O3—B1—C11—C16 | −133.32 (17) | O3—B1—C23—C28 | −137.73 (16) |
C23—B1—C11—C16 | 110.91 (19) | C11—B1—C23—C28 | −20.9 (2) |
C17—B1—C11—C16 | −19.3 (2) | C17—B1—C23—C28 | 109.28 (18) |
O3—B1—C11—C12 | 49.1 (2) | C28—C23—C24—F11 | −179.10 (15) |
C23—B1—C11—C12 | −66.7 (2) | B1—C23—C24—F11 | −2.5 (3) |
C17—B1—C11—C12 | 163.12 (15) | C28—C23—C24—C25 | 0.0 (3) |
C16—C11—C12—F1 | −179.68 (15) | B1—C23—C24—C25 | 176.62 (17) |
B1—C11—C12—F1 | −1.8 (3) | F11—C24—C25—F12 | 0.1 (3) |
C16—C11—C12—C13 | −0.3 (3) | C23—C24—C25—F12 | −179.01 (17) |
B1—C11—C12—C13 | 177.55 (17) | F11—C24—C25—C26 | 179.03 (17) |
F1—C12—C13—F2 | −1.0 (3) | C23—C24—C25—C26 | −0.1 (3) |
C11—C12—C13—F2 | 179.62 (17) | F12—C25—C26—F13 | −0.6 (3) |
F1—C12—C13—C14 | 179.59 (16) | C24—C25—C26—F13 | −179.57 (17) |
C11—C12—C13—C14 | 0.2 (3) | F12—C25—C26—C27 | 179.01 (17) |
F2—C13—C14—F3 | −0.2 (3) | C24—C25—C26—C27 | 0.1 (3) |
C12—C13—C14—F3 | 179.17 (17) | F13—C26—C27—F14 | 0.4 (3) |
F2—C13—C14—C15 | −179.01 (17) | C25—C26—C27—F14 | −179.27 (17) |
C12—C13—C14—C15 | 0.4 (3) | F13—C26—C27—C28 | 179.68 (16) |
F3—C14—C15—F4 | 0.3 (3) | C25—C26—C27—C28 | 0.0 (3) |
C13—C14—C15—F4 | 179.11 (17) | F14—C27—C28—F15 | 0.6 (2) |
F3—C14—C15—C16 | −179.62 (17) | C26—C27—C28—F15 | −178.71 (16) |
C13—C14—C15—C16 | −0.9 (3) | F14—C27—C28—C23 | 179.15 (15) |
F4—C15—C16—F5 | 1.5 (2) | C26—C27—C28—C23 | −0.1 (3) |
C14—C15—C16—F5 | −178.56 (16) | C24—C23—C28—F15 | 178.62 (15) |
F4—C15—C16—C11 | −179.21 (16) | B1—C23—C28—F15 | 2.1 (3) |
C14—C15—C16—C11 | 0.8 (3) | C24—C23—C28—C27 | 0.1 (3) |
C12—C11—C16—F5 | 179.13 (15) | B1—C23—C28—C27 | −176.40 (16) |
B1—C11—C16—F5 | 1.4 (3) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H4···O4 | 0.82 (2) | 1.78 (2) | 2.5968 (18) | 172 (3) |
O3—H3···O4ii | 0.84 | 1.87 | 2.682 (2) | 161 |
O4—H5···O1iii | 0.82 (2) | 1.96 (2) | 2.773 (2) | 174 (3) |
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x−1, y+1, z. |
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