In the crystal structure of the title salt, [Pd2(C15H11N2)2(C12H12N2)2](PF6)2, two (4,4′-dimethyl-2,2′-bipyridine)palladium(II) units are bridged by two pyrazolate ligands in an exodentate fashion. The six-membered ring consisting of the two Pd atoms and the four pyrazolyl N atoms has a boat-shaped conformation and the Pd atoms are four-coordinate in square-planar environments. The cation and both anions have crystallographically imposed mirror symmetry.
Supporting information
CCDC reference: 636756
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.012 Å
- R factor = 0.069
- wR factor = 0.197
- Data-to-parameter ratio = 22.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
PLAT602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure !
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... PD4
N1 N4 PD4
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.44
From the CIF: _reflns_number_total 8178
Count of symmetry unique reflns 4155
Completeness (_total/calc) 196.82%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 4023
Fraction of Friedel pairs measured 0.968
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Bis(µ-3,5-diphenylpyrazolato-
κ2N:
N')bis[(4,4'-dimethyl-2,2'-
bipyridine-
κ2N,
N')palladium(II)] bis(hexafluorophosphate)
top
Crystal data top
[Pd2(C15H11N2)2(C12H12N2)2](PF6)2 | Dx = 1.252 Mg m−3 |
Mr = 1309.73 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3m | Cell parameters from 13146 reflections |
Hall symbol: R 3 -2" | θ = 2.1–27.5° |
a = 38.2597 (8) Å | µ = 0.63 mm−1 |
c = 12.3356 (6) Å | T = 294 K |
V = 15637.7 (8) Å3 | Prism, yellow |
Z = 9 | 0.35 × 0.14 × 0.14 mm |
F(000) = 5904 | |
Data collection top
Rigaku Saturn70 diffractometer | 8178 independent reflections |
Radiation source: Rotating Anode | 7667 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.037 |
φ? ω? scans | θmax = 27.4°, θmin = 2.1° |
Absorption correction: multi-scan (Program?; Reference?) | h = −47→49 |
Tmin = 0.89, Tmax = 0.92 | k = −49→49 |
40292 measured reflections | l = −15→15 |
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)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.197 | w = 1/[σ2(Fo2) + (0.154P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
8178 reflections | Δρmax = 1.09 e Å−3 |
369 parameters | Δρmin = −1.44 e Å−3 |
23 restraints | Absolute structure: Flack (1983), with 4023 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (4) |
Special details top
Experimental. Lp corrections applied |
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 | 0.4134 (2) | 0.1485 (2) | 0.7425 (5) | 0.0773 (16) | |
H1 | 0.3932 | 0.1510 | 0.7778 | 0.093* | |
C2 | 0.4429 (3) | 0.1477 (3) | 0.8021 (6) | 0.093 (2) | |
H2 | 0.4424 | 0.1494 | 0.8773 | 0.112* | |
C3 | 0.4739 (2) | 0.1445 (3) | 0.7521 (8) | 0.093 (2) | |
C4 | 0.5056 (3) | 0.1416 (5) | 0.8166 (10) | 0.128 (4) | |
H4A | 0.5289 | 0.1680 | 0.8240 | 0.193* | |
H4B | 0.5130 | 0.1242 | 0.7801 | 0.193* | |
H4C | 0.4951 | 0.1309 | 0.8872 | 0.193* | |
C5 | 0.4733 (2) | 0.1421 (3) | 0.6405 (7) | 0.0836 (18) | |
H5 | 0.4931 | 0.1393 | 0.6042 | 0.100* | |
C6 | 0.44337 (18) | 0.1440 (2) | 0.5826 (5) | 0.0665 (13) | |
C7 | 0.44122 (19) | 0.1436 (2) | 0.4627 (6) | 0.0689 (13) | |
C8 | 0.4694 (2) | 0.1418 (2) | 0.3952 (7) | 0.0797 (16) | |
H8 | 0.4904 | 0.1394 | 0.4251 | 0.096* | |
C9 | 0.4663 (3) | 0.1435 (3) | 0.2836 (7) | 0.089 (2) | |
C10 | 0.4968 (4) | 0.1403 (4) | 0.2062 (9) | 0.124 (4) | |
H10A | 0.4849 | 0.1320 | 0.1356 | 0.186* | |
H10B | 0.5033 | 0.1209 | 0.2343 | 0.186* | |
H10C | 0.5209 | 0.1662 | 0.2009 | 0.186* | |
C11 | 0.4356 (2) | 0.1475 (3) | 0.2424 (7) | 0.088 (2) | |
H11 | 0.4335 | 0.1497 | 0.1679 | 0.106* | |
C12 | 0.4066 (2) | 0.1482 (2) | 0.3120 (5) | 0.0734 (15) | |
H12 | 0.3855 | 0.1508 | 0.2831 | 0.088* | |
C13 | 0.2984 (3) | 0.14921 (17) | 0.7863 (9) | 0.077 (2) | |
H13 | 0.2815 | 0.1408 | 0.8465 | 0.092* | |
C14 | 0.3136 (2) | 0.1282 (2) | 0.7324 (5) | 0.0677 (13) | |
C15 | 0.3045 (2) | 0.08540 (19) | 0.7507 (6) | 0.0687 (14) | |
C16 | 0.3138 (3) | 0.0742 (2) | 0.8483 (7) | 0.0867 (19) | |
H16 | 0.3272 | 0.0933 | 0.9024 | 0.104* | |
C17 | 0.3027 (3) | 0.0333 (3) | 0.8647 (8) | 0.100 (3) | |
H17 | 0.3087 | 0.0255 | 0.9302 | 0.119* | |
C18 | 0.2836 (3) | 0.0057 (3) | 0.7863 (10) | 0.100 (3) | |
H18 | 0.2767 | −0.0211 | 0.7977 | 0.120* | |
C19 | 0.2742 (3) | 0.0169 (3) | 0.6886 (11) | 0.105 (3) | |
H19 | 0.2608 | −0.0021 | 0.6345 | 0.126* | |
C20 | 0.2853 (3) | 0.0571 (2) | 0.6728 (7) | 0.0844 (19) | |
H20 | 0.2794 | 0.0648 | 0.6070 | 0.101* | |
C21 | 0.2941 (3) | 0.14705 (14) | 0.2822 (9) | 0.072 (2) | |
H21 | 0.2774 | 0.1387 | 0.2215 | 0.087* | |
C22 | 0.30953 (17) | 0.12589 (18) | 0.3385 (5) | 0.0610 (11) | |
C23 | 0.30332 (17) | 0.08556 (17) | 0.3112 (6) | 0.0651 (13) | |
C24 | 0.2929 (2) | 0.0707 (2) | 0.2069 (6) | 0.0753 (16) | |
H24 | 0.2897 | 0.0862 | 0.1541 | 0.090* | |
C25 | 0.2871 (2) | 0.0327 (2) | 0.1798 (6) | 0.0798 (17) | |
H25 | 0.2805 | 0.0236 | 0.1088 | 0.096* | |
C26 | 0.2908 (2) | 0.0087 (2) | 0.2545 (7) | 0.084 (2) | |
H26 | 0.2860 | −0.0169 | 0.2364 | 0.101* | |
C27 | 0.3020 (3) | 0.0237 (2) | 0.3578 (7) | 0.0837 (18) | |
H27 | 0.3051 | 0.0079 | 0.4100 | 0.100* | |
C28 | 0.3087 (2) | 0.0614 (2) | 0.3866 (6) | 0.0802 (17) | |
H28 | 0.3169 | 0.0708 | 0.4568 | 0.096* | |
N1 | 0.41259 (15) | 0.14575 (15) | 0.6324 (4) | 0.0625 (10) | |
N2 | 0.40938 (16) | 0.14526 (15) | 0.4198 (4) | 0.0632 (10) | |
N3 | 0.33563 (15) | 0.15012 (15) | 0.6478 (4) | 0.0624 (10) | |
N4 | 0.33285 (15) | 0.14859 (14) | 0.4200 (4) | 0.0610 (10) | |
F1 | 0.3917 (6) | 0.1958 (3) | 0.1381 (11) | 0.249 (10) | |
F2 | 0.3874 (4) | 0.1526 (3) | 0.0100 (12) | 0.287 (10) | |
F3 | 0.3837 (7) | 0.1919 (4) | −0.1151 (11) | 0.294 (13) | |
F4 | 0.3400 (4) | 0.1700 (2) | 0.0226 (17) | 0.263 (12) | |
F5 | 0.4352 (4) | 0.2176 (2) | 0.0005 (19) | 0.290 (13) | |
F6 | 0.5617 (5) | 0.1828 (4) | 0.4925 (14) | 0.290 (9) | |
F7 | 0.5798 (3) | 0.1596 (6) | 0.3511 (12) | 0.277 (14) | |
F8 | 0.5715 (3) | 0.1430 (7) | 0.6044 (10) | 0.288 (14) | |
F9 | 0.5312 (4) | 0.1163 (4) | 0.4608 (11) | 0.272 (10) | |
P1 | 0.3877 (4) | 0.1939 (2) | 0.0112 (11) | 0.285 (9) | |
P2 | 0.5754 (3) | 0.1508 (5) | 0.4775 (10) | 0.293 (9) | |
Pd1 | 0.370991 (12) | 0.145754 (12) | 0.53093 (5) | 0.05569 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.079 (4) | 0.090 (4) | 0.058 (3) | 0.039 (3) | 0.000 (3) | 0.007 (3) |
C2 | 0.089 (5) | 0.122 (6) | 0.056 (4) | 0.043 (5) | −0.018 (3) | 0.012 (4) |
C3 | 0.070 (4) | 0.107 (6) | 0.091 (5) | 0.036 (4) | −0.018 (4) | 0.017 (4) |
C4 | 0.096 (6) | 0.176 (11) | 0.114 (8) | 0.068 (7) | −0.033 (6) | 0.019 (7) |
C5 | 0.060 (3) | 0.094 (5) | 0.094 (5) | 0.036 (3) | −0.004 (3) | 0.011 (4) |
C6 | 0.064 (3) | 0.077 (3) | 0.064 (3) | 0.039 (3) | −0.001 (2) | 0.001 (2) |
C7 | 0.067 (3) | 0.073 (3) | 0.065 (3) | 0.034 (3) | 0.003 (2) | 0.000 (3) |
C8 | 0.070 (3) | 0.087 (4) | 0.087 (4) | 0.044 (3) | 0.009 (3) | −0.001 (3) |
C9 | 0.082 (4) | 0.103 (5) | 0.078 (4) | 0.042 (4) | 0.016 (3) | −0.015 (4) |
C10 | 0.109 (7) | 0.164 (10) | 0.105 (7) | 0.072 (7) | 0.039 (6) | −0.018 (7) |
C11 | 0.080 (4) | 0.106 (5) | 0.066 (4) | 0.037 (4) | 0.012 (3) | −0.013 (4) |
C12 | 0.073 (3) | 0.093 (4) | 0.054 (3) | 0.041 (3) | 0.004 (2) | −0.006 (3) |
C13 | 0.087 (6) | 0.077 (4) | 0.069 (5) | 0.043 (3) | 0.024 (5) | 0.012 (2) |
C14 | 0.070 (3) | 0.067 (3) | 0.065 (3) | 0.033 (3) | 0.012 (3) | 0.012 (3) |
C15 | 0.072 (3) | 0.065 (3) | 0.071 (3) | 0.035 (3) | 0.016 (3) | 0.015 (3) |
C16 | 0.097 (5) | 0.087 (4) | 0.078 (4) | 0.047 (4) | 0.015 (4) | 0.024 (4) |
C17 | 0.119 (6) | 0.111 (6) | 0.092 (5) | 0.075 (6) | 0.025 (5) | 0.040 (5) |
C18 | 0.095 (5) | 0.084 (5) | 0.131 (8) | 0.052 (4) | 0.021 (5) | 0.028 (5) |
C19 | 0.103 (6) | 0.079 (4) | 0.132 (8) | 0.045 (4) | 0.010 (6) | −0.002 (5) |
C20 | 0.096 (5) | 0.078 (4) | 0.087 (5) | 0.049 (4) | 0.009 (4) | 0.010 (4) |
C21 | 0.067 (4) | 0.066 (3) | 0.083 (5) | 0.034 (2) | −0.012 (4) | −0.006 (2) |
C22 | 0.064 (3) | 0.059 (3) | 0.057 (3) | 0.029 (2) | −0.009 (2) | −0.004 (2) |
C23 | 0.060 (3) | 0.057 (3) | 0.075 (4) | 0.027 (2) | −0.002 (2) | −0.010 (2) |
C24 | 0.074 (3) | 0.075 (3) | 0.067 (4) | 0.030 (3) | −0.011 (3) | −0.016 (3) |
C25 | 0.074 (3) | 0.081 (4) | 0.078 (4) | 0.033 (3) | −0.002 (3) | −0.024 (3) |
C26 | 0.076 (4) | 0.077 (4) | 0.096 (5) | 0.035 (3) | −0.005 (3) | −0.036 (4) |
C27 | 0.107 (5) | 0.073 (4) | 0.082 (4) | 0.053 (4) | −0.004 (4) | −0.009 (3) |
C28 | 0.095 (4) | 0.066 (3) | 0.082 (4) | 0.042 (3) | −0.007 (3) | −0.002 (3) |
N1 | 0.065 (2) | 0.070 (3) | 0.054 (2) | 0.035 (2) | 0.0003 (19) | 0.0051 (19) |
N2 | 0.067 (2) | 0.069 (3) | 0.055 (2) | 0.035 (2) | −0.0029 (19) | −0.0052 (19) |
N3 | 0.064 (2) | 0.062 (2) | 0.064 (3) | 0.034 (2) | 0.0103 (19) | 0.007 (2) |
N4 | 0.065 (2) | 0.058 (2) | 0.062 (3) | 0.032 (2) | −0.0101 (19) | −0.011 (2) |
F1 | 0.26 (2) | 0.245 (17) | 0.25 (2) | 0.129 (12) | −0.079 (19) | −0.039 (10) |
F2 | 0.28 (2) | 0.29 (2) | 0.31 (3) | 0.154 (17) | 0.02 (2) | −0.065 (19) |
F3 | 0.28 (3) | 0.28 (2) | 0.33 (4) | 0.139 (15) | −0.04 (3) | −0.021 (16) |
F4 | 0.28 (3) | 0.28 (2) | 0.23 (3) | 0.140 (13) | −0.05 (2) | −0.027 (11) |
F5 | 0.27 (3) | 0.30 (3) | 0.29 (3) | 0.134 (14) | −0.02 (3) | −0.009 (13) |
F6 | 0.231 (17) | 0.29 (2) | 0.36 (3) | 0.134 (16) | −0.038 (18) | −0.03 (2) |
F7 | 0.278 (19) | 0.29 (3) | 0.27 (3) | 0.143 (14) | 0.077 (12) | 0.15 (2) |
F8 | 0.29 (2) | 0.29 (3) | 0.29 (3) | 0.143 (14) | 0.079 (12) | 0.16 (2) |
F9 | 0.271 (17) | 0.283 (18) | 0.272 (17) | 0.146 (15) | 0.047 (14) | 0.188 (16) |
P1 | 0.278 (19) | 0.289 (14) | 0.29 (2) | 0.139 (10) | −0.096 (18) | −0.048 (9) |
P2 | 0.290 (14) | 0.29 (2) | 0.30 (2) | 0.147 (10) | 0.067 (8) | 0.133 (17) |
Pd1 | 0.0587 (2) | 0.0602 (2) | 0.0507 (2) | 0.03168 (16) | −0.00119 (14) | −0.00112 (14) |
Geometric parameters (Å, º) top
C1—C2 | 1.359 (11) | C18—H18 | 0.9300 |
C1—N1 | 1.362 (8) | C19—C20 | 1.388 (12) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.399 (15) | C20—H20 | 0.9300 |
C2—H2 | 0.9300 | C21—C22i | 1.402 (8) |
C3—C5 | 1.379 (13) | C21—C22 | 1.402 (8) |
C3—C4 | 1.498 (11) | C21—H21 | 0.9300 |
C4—H4A | 0.9600 | C22—N4 | 1.336 (7) |
C4—H4B | 0.9600 | C22—C23 | 1.478 (8) |
C4—H4C | 0.9600 | C23—C24 | 1.382 (10) |
C5—C6 | 1.382 (10) | C23—C28 | 1.398 (10) |
C5—H5 | 0.9300 | C24—C25 | 1.397 (10) |
C6—N1 | 1.358 (8) | C24—H24 | 0.9300 |
C6—C7 | 1.481 (9) | C25—C26 | 1.356 (13) |
C7—N2 | 1.360 (9) | C25—H25 | 0.9300 |
C7—C8 | 1.391 (10) | C26—C27 | 1.375 (11) |
C8—C9 | 1.386 (13) | C26—H26 | 0.9300 |
C8—H8 | 0.9300 | C27—C28 | 1.379 (9) |
C9—C11 | 1.359 (14) | C27—H27 | 0.9300 |
C9—C10 | 1.558 (11) | C28—H28 | 0.9300 |
C10—H10A | 0.9600 | Pd1—N1 | 2.025 (5) |
C10—H10B | 0.9600 | Pd1—N2 | 2.016 (5) |
C10—H10C | 0.9600 | N3—N3i | 1.354 (10) |
C11—C12 | 1.413 (10) | Pd1—N3 | 2.040 (5) |
C11—H11 | 0.9300 | N4—N4i | 1.365 (9) |
C12—N2 | 1.343 (8) | Pd1—N4 | 2.042 (5) |
C12—H12 | 0.9300 | F1—P1 | 1.571 (19) |
C13—C14i | 1.375 (9) | F2—P1 | 1.575 (15) |
C13—C14 | 1.375 (9) | F3—P1 | 1.564 (19) |
C13—H13 | 0.9300 | F4—P1 | 1.59 (2) |
C14—N3 | 1.340 (8) | F5—P1 | 1.58 (2) |
C14—C15 | 1.511 (9) | F6—P2 | 1.57 (2) |
C15—C20 | 1.357 (12) | F7—P2 | 1.59 (2) |
C15—C16 | 1.382 (11) | F8—P2 | 1.587 (9) |
C16—C17 | 1.417 (12) | F9—P2 | 1.55 (2) |
C16—H16 | 0.9300 | P1—F2i | 1.57 (2) |
C17—C18 | 1.348 (16) | P2—F9ii | 1.55 (2) |
C17—H17 | 0.9300 | P2—F6ii | 1.57 (3) |
C18—C19 | 1.386 (17) | Pd1—Pd1i | 3.0410 (8) |
| | | |
C2—C1—N1 | 121.6 (8) | C21—C22—C23 | 126.6 (6) |
C2—C1—H1 | 119.2 | C24—C23—C28 | 117.0 (6) |
N1—C1—H1 | 119.2 | C24—C23—C22 | 120.3 (6) |
C1—C2—C3 | 121.0 (7) | C28—C23—C22 | 122.6 (6) |
C1—C2—H2 | 119.5 | C23—C24—C25 | 121.0 (7) |
C3—C2—H2 | 119.5 | C23—C24—H24 | 119.5 |
C5—C3—C2 | 117.3 (7) | C25—C24—H24 | 119.5 |
C5—C3—C4 | 121.0 (10) | C26—C25—C24 | 121.6 (7) |
C2—C3—C4 | 121.7 (9) | C26—C25—H25 | 119.2 |
C3—C4—H4A | 109.5 | C24—C25—H25 | 119.2 |
C3—C4—H4B | 109.5 | C25—C26—C27 | 117.7 (6) |
H4A—C4—H4B | 109.5 | C25—C26—H26 | 121.1 |
C3—C4—H4C | 109.5 | C27—C26—H26 | 121.1 |
H4A—C4—H4C | 109.5 | C26—C27—C28 | 122.0 (8) |
H4B—C4—H4C | 109.5 | C26—C27—H27 | 119.0 |
C3—C5—C6 | 120.0 (7) | C28—C27—H27 | 119.0 |
C3—C5—H5 | 120.0 | C27—C28—C23 | 120.6 (7) |
C6—C5—H5 | 120.0 | C27—C28—H28 | 119.7 |
N1—C6—C5 | 122.0 (7) | C23—C28—H28 | 119.7 |
N1—C6—C7 | 114.1 (5) | C6—N1—C1 | 117.9 (6) |
C5—C6—C7 | 123.9 (6) | C6—N1—Pd1 | 114.9 (4) |
N2—C7—C8 | 120.3 (7) | C1—N1—Pd1 | 127.1 (5) |
N2—C7—C6 | 115.7 (6) | C12—N2—C7 | 120.1 (6) |
C8—C7—C6 | 124.0 (7) | C12—N2—Pd1 | 125.7 (4) |
C9—C8—C7 | 120.4 (7) | C7—N2—Pd1 | 114.2 (4) |
C9—C8—H8 | 119.8 | C14—N3—N3i | 108.1 (4) |
C7—C8—H8 | 119.8 | C14—N3—Pd1 | 137.3 (4) |
C11—C9—C8 | 118.4 (7) | N3i—N3—Pd1 | 114.42 (14) |
C11—C9—C10 | 120.2 (9) | C22—N4—N4i | 108.4 (3) |
C8—C9—C10 | 121.3 (9) | C22—N4—Pd1 | 137.1 (4) |
C9—C10—H10A | 109.5 | N1—N4—Pd4i | 114.22 (13) |
C9—C10—H10B | 109.5 | F3—P1—F1 | 179.9 (10) |
H10A—C10—H10B | 109.5 | F3—P1—F2 | 89.4 (10) |
C9—C10—H10C | 109.5 | F1—P1—F2 | 90.6 (10) |
H10A—C10—H10C | 109.5 | F3—P1—F2i | 89.4 (10) |
H10B—C10—H10C | 109.5 | F1—P1—F2i | 90.6 (10) |
C9—C11—C12 | 120.5 (8) | F2—P1—F2i | 178.6 (9) |
C9—C11—H11 | 119.8 | F3—P1—F5 | 90.1 (14) |
C12—C11—H11 | 119.8 | F1—P1—F5 | 90.0 (13) |
N2—C12—C11 | 120.2 (7) | F2—P1—F5 | 90.3 (10) |
N2—C12—H12 | 119.9 | F2i—P1—F5 | 90.3 (10) |
C11—C12—H12 | 119.9 | F3—P1—F4 | 90.2 (14) |
C14i—C13—C14 | 105.4 (8) | F1—P1—F4 | 89.8 (13) |
C14i—C13—H13 | 127.3 | F2—P1—F4 | 89.6 (4) |
C14—C13—H13 | 127.3 | F2i—P1—F4 | 89.6 (4) |
N3—C14—C13 | 109.1 (6) | F5—P1—F4 | 179.7 (9) |
N3—C14—C15 | 121.8 (6) | F9—P2—F9ii | 83.1 (14) |
C13—C14—C15 | 128.7 (6) | F9—P2—F6ii | 175.0 (13) |
C20—C15—C16 | 119.4 (7) | F9ii—P2—F6ii | 92.0 (6) |
C20—C15—C14 | 119.9 (6) | F9—P2—F6 | 92.0 (6) |
C16—C15—C14 | 120.7 (7) | F9ii—P2—F6 | 175.0 (13) |
C15—C16—C17 | 119.0 (9) | F6ii—P2—F6 | 93.0 (15) |
C15—C16—H16 | 120.5 | F9—P2—F7 | 90.3 (6) |
C17—C16—H16 | 120.5 | F9ii—P2—F7 | 90.3 (6) |
C18—C17—C16 | 120.7 (8) | F6ii—P2—F7 | 89.5 (12) |
C18—C17—H17 | 119.7 | F6—P2—F7 | 89.5 (12) |
C16—C17—H17 | 119.7 | F9—P2—F8 | 90.6 (12) |
C17—C18—C19 | 120.2 (8) | F9ii—P2—F8 | 90.6 (12) |
C17—C18—H18 | 119.9 | F6ii—P2—F8 | 89.7 (6) |
C19—C18—H18 | 119.9 | F6—P2—F8 | 89.7 (6) |
C18—C19—C20 | 118.9 (11) | F7—P2—F8 | 178.8 (9) |
C18—C19—H19 | 120.6 | N1—Pd1—N2 | 81.03 (19) |
C20—C19—H19 | 120.6 | N1—Pd1—N3 | 96.7 (2) |
C15—C20—C19 | 121.9 (9) | N1—Pd1—N4 | 175.3 (2) |
C15—C20—H20 | 119.1 | N2—Pd1—N3 | 175.8 (2) |
C19—C20—H20 | 119.1 | N2—Pd1—N4 | 95.0 (2) |
C22i—C21—C22 | 104.1 (8) | N3—Pd1—N4 | 87.0 (2) |
C22i—C21—H21 | 128.0 | N2—Pd1—Pd1i | 111.94 (15) |
C22—C21—H21 | 128.0 | N1—Pd1—Pd1i | 113.15 (14) |
N4—C22—C21 | 109.5 (6) | N3—Pd1—Pd1i | 65.58 (14) |
N4—C22—C23 | 123.8 (5) | N4—Pd1—Pd1i | 65.78 (13) |
| | | |
N1—C1—C2—C3 | 0.7 (14) | C22—C23—C28—C27 | 179.0 (7) |
C1—C2—C3—C5 | 0.1 (14) | C5—C6—N1—C1 | 4.6 (10) |
C1—C2—C3—C4 | −177.1 (10) | C7—C6—N1—C1 | −176.5 (6) |
C2—C3—C5—C6 | 1.5 (13) | C5—C6—N1—Pd1 | −177.3 (6) |
C4—C3—C5—C6 | 178.7 (9) | C7—C6—N1—Pd1 | 1.5 (7) |
C3—C5—C6—N1 | −4.0 (12) | C2—C1—N1—Pd1 | 179.3 (6) |
C3—C5—C6—C7 | 177.3 (7) | C11—C12—N2—C7 | 3.3 (11) |
N1—C6—C7—N2 | 0.6 (8) | C11—C12—N2—Pd1 | −180.0 (6) |
C5—C6—C7—N2 | 179.4 (7) | C8—C7—N2—C12 | −4.9 (10) |
N1—C6—C7—C8 | −179.8 (7) | C6—C7—N2—C12 | 174.7 (6) |
C5—C6—C7—C8 | −1.0 (11) | C8—C7—N2—Pd1 | 178.0 (5) |
N2—C7—C8—C9 | 2.9 (11) | C6—C7—N2—Pd1 | −2.4 (7) |
C6—C7—C8—C9 | −176.7 (7) | C13—C14—N3—N3i | 1.3 (8) |
C7—C8—C9—C11 | 0.8 (13) | C15—C14—N3—N3i | 174.8 (5) |
C7—C8—C9—C10 | −178.3 (9) | C13—C14—N3—Pd1 | 175.8 (7) |
C8—C9—C11—C12 | −2.4 (14) | C15—C14—N3—Pd1 | −10.8 (11) |
C10—C9—C11—C12 | 176.6 (9) | C21—C22—N4—N4i | 0.8 (7) |
C9—C11—C12—N2 | 0.5 (13) | C23—C22—N4—N4i | 178.0 (5) |
C14i—C13—C14—N3 | −2.1 (12) | C21—C22—N4—Pd1 | −172.3 (6) |
C14i—C13—C14—C15 | −174.9 (5) | C23—C22—N4—Pd1 | 4.9 (10) |
N3—C14—C15—C20 | −57.7 (10) | C12—N2—Pd1—N1 | −174.4 (6) |
C13—C14—C15—C20 | 114.4 (10) | C7—N2—Pd1—N1 | 2.5 (4) |
N3—C14—C15—C16 | 125.4 (7) | C12—N2—Pd1—N4 | 2.9 (6) |
C13—C14—C15—C16 | −62.6 (12) | C7—N2—Pd1—N4 | 179.8 (4) |
C20—C15—C16—C17 | −0.5 (11) | C12—N2—Pd1—Pd1i | −63.0 (6) |
C14—C15—C16—C17 | 176.4 (7) | C7—N2—Pd1—Pd1i | 113.9 (4) |
C15—C16—C17—C18 | 0.4 (13) | C6—N1—Pd1—N2 | −2.2 (4) |
C16—C17—C18—C19 | −0.5 (14) | C1—N1—Pd1—N2 | 175.6 (6) |
C17—C18—C19—C20 | 0.7 (15) | C6—N1—Pd1—N3 | −178.6 (4) |
C16—C15—C20—C19 | 0.8 (12) | C1—N1—Pd1—N3 | −0.7 (6) |
C14—C15—C20—C19 | −176.2 (7) | C6—N1—Pd1—Pd1i | −112.3 (4) |
C18—C19—C20—C15 | −0.9 (14) | C1—N1—Pd1—Pd1i | 65.5 (6) |
C22i—C21—C22—N4 | −1.2 (10) | C14—N3—Pd1—N1 | −61.8 (7) |
C22i—C21—C22—C23 | −178.3 (4) | N3i—N3—Pd1—N1 | 112.4 (5) |
N4—C22—C23—C24 | −154.6 (6) | C14—N3—Pd1—N4 | 121.1 (7) |
C21—C22—C23—C24 | 22.1 (11) | N3i—N3—Pd1—N4 | −64.7 (5) |
N4—C22—C23—C28 | 23.4 (10) | C14—N3—Pd1—Pd1i | −174.2 (8) |
C21—C22—C23—C28 | −159.8 (8) | N3i—N3—Pd1—Pd1i | 0.0 |
C28—C23—C24—C25 | 1.6 (10) | C22—N4—Pd1—N2 | 61.0 (7) |
C22—C23—C24—C25 | 179.8 (6) | N4i—N4—Pd1—N2 | −111.8 (4) |
C23—C24—C25—C26 | 0.9 (11) | C22—N4—Pd1—N3 | −122.7 (7) |
C24—C25—C26—C27 | −2.2 (11) | N4i—N4—Pd1—N3 | 64.5 (4) |
C25—C26—C27—C28 | 0.9 (13) | C22—N4—Pd1—Pd1i | 172.8 (7) |
C26—C27—C28—C23 | 1.7 (13) | N4i—N4—Pd1—Pd1i | 0.0 |
C24—C23—C28—C27 | −2.9 (11) | | |
Symmetry codes: (i) x, x−y, z; (ii) −x+y+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···F3iii | 0.93 | 2.21 | 3.00 (3) | 142 |
C1—H1···F3iv | 0.93 | 2.21 | 3.00 (3) | 142 |
C8—H8···F6 | 0.93 | 2.52 | 3.29 (2) | 140 |
C8—H8···F9 | 0.93 | 2.19 | 3.08 (2) | 161 |
C12—H12···F1 | 0.93 | 2.41 | 3.05 (1) | 125 |
C21—H21···F9v | 0.93 | 2.53 | 3.35 (1) | 147 |
C21—H21···F9vi | 0.93 | 2.53 | 3.35 (1) | 147 |
Symmetry codes: (iii) x, y, z+1; (iv) x, x−y, z+1; (v) −y+1/3, x−y−1/3, z−1/3; (vi) −y+1/3, −x+2/3, z−1/3. |