Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615021968/fp3018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615021968/fp3018Isup2.hkl |
CCDC reference: 1415104
\ Iron is of interest as catalyst material, not only because of its established use in the Haber–Bosch process, but also because of its high abundance and low toxicity (Bauer & Knölker, 2015; Riener et al., 2014). With the rise of N-heterocyclic carbenes (NHCs) as a ligand class in homogeneous catalysis, iron–NHC complexes have also attracted increasing attention in recent years (Riener et al., 2014). However, especially in the field of homogeneous oxidation catalysis, iron-based catalysts, including iron–NHC complexes, still face problems in terms of stability under oxidative conditions (Talsi & Bryliakov, 2012).
Decomposition of the respective catalysts can be caused by self-oxidation of the ligand environment, leading to degradation of the organic ligand structure (England et al., 2008). It is not only strong oxidants, such as hydrogen peroxide or alkyl peroxides, that can cause ligand degradation. Depending on the solvent and reaction conditions, dioxygen can also induce undesired side reactions.
In this work, a previously reported FeII–NHC complex, [Fe(NCCN)(MeCN)(PMe3)](PF6)2 {NCCN is bis[3-(pyridin-2-yl)-1H-imidazol-1-yl]methane}, with one labile coordination site (Haslinger et al., 2014), is exposed to air in acetone solution, leading to slow degradation of the ligand environment (Scheme 1). The decomposition product of the organic ligand is trapped by coordination to the still-intact FeII–NHC complexes in solution via the aforementioned labile coordination site. The resulting structure was identified by single-crystal X-ray diffraction as [1,1'-bis(pyridin-2-yl)-2,2-bi(1H-imidazole)-κN3][3,3'-\ bis(pyridin-2-yl-κN)-1,1'-methanediylbi(1H-imidazol-2-yl-\ κC2)](trimethylphosphane-κP)iron(II) bis(hexafluoridophosphate), (I). It is of interest that, in the organic decomposition product of the former NCCN ligand, a new C—C bond is formed between the NHC groups and, in addition, the methylene bridge is cleaved.
The chemicals used were purchased from commercial suppliers and used without further purification. For the preparation of [Fe(NCCN)(MeCN)(PMe3)](PF6)2, water- and oxygen-free acetonitrile was obtained from a solvent purification system by MBraun. Single crystals of (I) were measured in the SC–XRD laboratory of the Catalysis Research Center at Technische Universität München.
The synthesis of [Fe(NCCN)(MeCN)(PMe3)](PF6)2 was performed according to known literature procedures [References needed unless the reaction is routine].
[Fe(NCCN)(MeCN)(PMe3)](PF6)2 (10 mg) was dissolved in acetone (HPLC grade, 2 ml) under air and a fraction of the solution was transferred into an NMR tube. The NMR tube was placed in a Schlenk tube filled with diethyl ether (10 ml) and the Schlenk tube was sealed tightly under air. Within six weeks, single crystals of (I) suitable for X-ray diffraction were collected after slow diffusion of the diethyl ether into the solution of [Fe(NCCN)(MeCN)(PMe3)](PF6)2 in acetone. A crystal was selected, fixed on top of a glass fibre using perfluorinated ether and transferred to the diffractometer.
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms could not be located in difference Fourier maps and were calculated in ideal positions (riding model), with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for CH3 groups, C—H = 0.99 Å and Uiso(H) = 1.2Ueq(C) for CH2 groups, and C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for CH groups. Split-layer position refinement was used for atoms F7, F8, F9, F10, F11, F12, C34, C35 and C36. SIMU and DELU [Please rephrase using non-software-specific terms] restraints were applied to the following atoms to ensure reasonable ellipsoids: C34, C35, C36, C34A, C35A, C36A, F7, F8, F9, F10, F11, F12, F7A, F8A, F9A, F10A, F11A and F12A.
In the title compound, (I) (Fig. 1), the FeII cation is coordinated in an octahedral manner by an equatorial tetradentate NCCN ligand, one PMe3 ligand in an axial position and the N-bound decomposition product of the former NCCN ligand in the other axial position trans to PMe3. For the equatorial coordination of the tetradentate ligand, the Fe—Npy (py is pyridine) bond lengths are 2.080 (3) and 2.067 (3) Å, and the Fe—CNHC bond lengths are 1.818 (4) and 1.812 (4) Å (Table 2).
The four equatorially coordinating atoms, N3, N6, C1 and C10, and atom Fe1 are located in one plane. These findings are in accordance with other FeII complexes bearing the same equatorial NCCN ligand (Haslinger et al., 2014; Raba et al., 2012).
The Fe1—P1 bond length [2.2179 (13) Å; Table 2] is slightly shorter than in the related FeII complex [Revised text OK?] with both axial positions coordinated by PMe3 ligands (Haslinger et al., 2014).
The imidazole group trans to the PMe3 ligand of (I) is coordinated with an Fe1—N8 bond length of 2.047 (3) Å (Table 2).
A P1—Fe1—N8 angle of 171.70 (8)° (Table 2) indicates repulsion of the axial ligands by the H atoms of the methylene bridge of the equatorial NCCN ligand.
The planes spanned by the two C-coupled imidazole rings are twisted with an angle of 72.72(s.u.?)° and the bond length of the coupled C atoms [C18—C26 = 1.458 (5) Å] is slightly shorter than expected for a single bond, but still significantly longer than a double bond (Clayden et al., 2001).
As the axial diimidazole ligand is not charged and two PF6- anions per Fe atom are found, Fe is in the +II oxidation state.
The packing of (I) is shown in Fig. 2, with no relevant packing effects detectable.
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009) and enCIFer (Allen et al., 2004).
[Fe(C17H14N6)(C16H12N6)(C3H9P)](PF6)2 | Z = 2 |
Mr = 1012.52 | F(000) = 1028 |
Triclinic, P1 | Dx = 1.611 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1146 (4) Å | Cell parameters from 9982 reflections |
b = 12.1591 (5) Å | θ = 2.4–25.4° |
c = 17.7002 (7) Å | µ = 0.58 mm−1 |
α = 97.219 (2)° | T = 123 K |
β = 97.020 (2)° | Fragment, red |
γ = 102.060 (2)° | 0.25 × 0.22 × 0.13 mm |
V = 2087.05 (15) Å3 |
Bruker APEXII CCD area-detector diffractometer | 7607 independent reflections |
Radiation source: rotating anode FR591 | 5543 reflections with I > 2σ(I) |
MONTEL optic monochromator | Rint = 0.095 |
Detector resolution: 16 pixels mm-1 | θmax = 25.4°, θmin = 1.7° |
φ and ω rotation scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | k = −14→14 |
Tmin = 0.414, Tmax = 0.745 | l = −21→21 |
52121 measured reflections |
Refinement on F2 | 120 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0432P)2 + 3.9609P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
7607 reflections | Δρmax = 0.75 e Å−3 |
666 parameters | Δρmin = −0.73 e Å−3 |
[Fe(C17H14N6)(C16H12N6)(C3H9P)](PF6)2 | γ = 102.060 (2)° |
Mr = 1012.52 | V = 2087.05 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.1146 (4) Å | Mo Kα radiation |
b = 12.1591 (5) Å | µ = 0.58 mm−1 |
c = 17.7002 (7) Å | T = 123 K |
α = 97.219 (2)° | 0.25 × 0.22 × 0.13 mm |
β = 97.020 (2)° |
Bruker APEXII CCD area-detector diffractometer | 7607 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 5543 reflections with I > 2σ(I) |
Tmin = 0.414, Tmax = 0.745 | Rint = 0.095 |
52121 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 120 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.75 e Å−3 |
7607 reflections | Δρmin = −0.73 e Å−3 |
666 parameters |
Experimental. Diffractometer operator S. Haslinger scanspeed 20 s per frame dx 35 mm 2822 frames measured in 7 data sets phi-scans with delta_phi = 0.5 omega-scans with delta_omega = 0.5 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.55140 (5) | 0.10589 (4) | 0.25424 (3) | 0.0219 (2) | |
P1 | 0.67882 (11) | 0.00708 (10) | 0.31566 (6) | 0.0344 (3) | |
P3 | −0.01542 (11) | 0.81332 (9) | 0.10108 (7) | 0.0396 (3) | |
P2 | 0.07282 (11) | 0.29379 (9) | 0.55139 (6) | 0.0327 (3) | |
N1 | 0.5022 (3) | 0.2190 (3) | 0.38906 (16) | 0.0270 (10) | |
N2 | 0.6876 (3) | 0.3151 (3) | 0.36119 (17) | 0.0323 (10) | |
N3 | 0.3927 (3) | 0.0490 (2) | 0.31436 (16) | 0.0236 (9) | |
N4 | 0.8024 (3) | 0.2768 (3) | 0.25216 (18) | 0.0355 (10) | |
N5 | 0.7366 (3) | 0.1440 (3) | 0.15325 (17) | 0.0322 (10) | |
N6 | 0.5477 (3) | 0.0014 (3) | 0.15205 (16) | 0.0261 (10) | |
N7 | 0.2937 (3) | 0.2808 (2) | 0.13328 (16) | 0.0221 (9) | |
F7 | 0.1493 (8) | 0.8291 (8) | 0.1094 (6) | 0.082 (3) | 0.534 (5) |
F7A | 0.0457 (10) | 0.8292 (10) | 0.0319 (5) | 0.103 (3) | 0.466 (5) |
F8 | −0.1712 (10) | 0.7998 (10) | 0.0866 (7) | 0.085 (3) | 0.534 (5) |
N8 | 0.4136 (3) | 0.1751 (2) | 0.19260 (15) | 0.0187 (8) | |
F8A | −0.0924 (11) | 0.7881 (9) | 0.1750 (6) | 0.117 (3) | 0.466 (5) |
F9 | −0.0138 (6) | 0.7203 (7) | 0.0257 (4) | 0.086 (2) | 0.534 (5) |
N9 | 0.1581 (3) | 0.4128 (3) | 0.1295 (2) | 0.0370 (11) | |
F9A | −0.0511 (6) | 0.6775 (5) | 0.0789 (6) | 0.062 (2) | 0.466 (5) |
N10 | 0.6340 (3) | 0.3993 (3) | 0.1547 (2) | 0.0382 (11) | |
F10 | 0.0192 (9) | 0.9099 (8) | 0.0428 (5) | 0.110 (3) | 0.534 (5) |
F10A | 0.1230 (11) | 0.8118 (10) | 0.1460 (6) | 0.094 (3) | 0.466 (5) |
N11 | 0.5226 (3) | 0.4747 (3) | 0.2416 (2) | 0.0380 (11) | |
F11 | 0.0114 (10) | 0.9165 (8) | 0.1648 (5) | 0.076 (3) | 0.534 (5) |
F11A | −0.0035 (11) | 0.9437 (8) | 0.1289 (6) | 0.072 (3) | 0.466 (5) |
F12 | −0.0259 (8) | 0.7246 (7) | 0.1498 (5) | 0.096 (3) | 0.534 (5) |
N12 | 0.3521 (4) | 0.3951 (3) | 0.3105 (2) | 0.0477 (14) | |
F12A | −0.1504 (15) | 0.8144 (12) | 0.0531 (7) | 0.090 (3) | 0.466 (5) |
C1 | 0.5884 (4) | 0.2197 (3) | 0.3362 (2) | 0.0253 (11) | |
C2 | 0.5467 (4) | 0.3137 (3) | 0.4470 (2) | 0.0377 (14) | |
C3 | 0.6619 (5) | 0.3729 (4) | 0.4291 (2) | 0.0413 (14) | |
C4 | 0.3895 (4) | 0.1258 (3) | 0.3764 (2) | 0.0259 (11) | |
C5 | 0.2874 (4) | 0.1134 (4) | 0.4222 (2) | 0.0369 (14) | |
C6 | 0.1842 (4) | 0.0159 (4) | 0.4042 (2) | 0.0456 (14) | |
C7 | 0.1856 (4) | −0.0653 (4) | 0.3428 (2) | 0.0403 (14) | |
C8 | 0.2901 (4) | −0.0451 (3) | 0.2996 (2) | 0.0316 (12) | |
C9 | 0.8082 (4) | 0.3503 (4) | 0.3251 (2) | 0.0430 (14) | |
C10 | 0.7024 (4) | 0.1832 (3) | 0.2222 (2) | 0.0289 (11) | |
C11 | 0.8981 (4) | 0.2959 (4) | 0.2020 (2) | 0.0443 (16) | |
C12 | 0.8581 (4) | 0.2144 (4) | 0.1404 (3) | 0.0429 (14) | |
C13 | 0.6523 (4) | 0.0415 (4) | 0.1142 (2) | 0.0322 (14) | |
C14 | 0.6751 (5) | −0.0147 (4) | 0.0456 (2) | 0.0412 (16) | |
C15 | 0.5850 (5) | −0.1151 (4) | 0.0138 (2) | 0.0477 (16) | |
C16 | 0.4760 (5) | −0.1578 (4) | 0.0498 (2) | 0.0443 (16) | |
C17 | 0.4610 (4) | −0.0974 (3) | 0.1187 (2) | 0.0335 (12) | |
C18 | 0.4167 (3) | 0.2779 (3) | 0.17353 (19) | 0.0205 (10) | |
C19 | 0.2092 (4) | 0.1756 (3) | 0.1274 (2) | 0.0261 (11) | |
C20 | 0.2832 (3) | 0.1115 (3) | 0.1626 (2) | 0.0252 (11) | |
C21 | 0.2604 (4) | 0.3781 (3) | 0.1030 (2) | 0.0241 (11) | |
C22 | 0.3324 (4) | 0.4256 (3) | 0.0501 (2) | 0.0365 (12) | |
C23 | 0.2959 (5) | 0.5189 (4) | 0.0231 (3) | 0.0468 (17) | |
C24 | 0.1919 (4) | 0.5585 (4) | 0.0506 (3) | 0.0463 (17) | |
C25 | 0.1251 (5) | 0.5033 (4) | 0.1019 (3) | 0.0506 (17) | |
C26 | 0.5270 (4) | 0.3802 (3) | 0.1912 (2) | 0.0283 (12) | |
C27 | 0.7017 (4) | 0.5101 (4) | 0.1843 (3) | 0.0504 (16) | |
C28 | 0.6354 (5) | 0.5568 (4) | 0.2357 (3) | 0.0550 (18) | |
C29 | 0.4156 (4) | 0.4881 (4) | 0.2852 (2) | 0.0402 (12) | |
C30 | 0.3829 (5) | 0.5910 (4) | 0.2979 (4) | 0.069 (2) | |
C31 | 0.2781 (6) | 0.5994 (5) | 0.3397 (4) | 0.083 (3) | |
C32 | 0.2092 (5) | 0.5060 (5) | 0.3659 (3) | 0.0644 (19) | |
C33 | 0.2483 (5) | 0.4067 (5) | 0.3499 (2) | 0.0540 (18) | |
C34 | 0.6995 (11) | 0.0397 (9) | 0.4198 (5) | 0.066 (3) | 0.579 (6) |
C34A | 0.8074 (14) | 0.0709 (13) | 0.3919 (8) | 0.073 (4) | 0.421 (6) |
C35 | 0.8628 (8) | 0.0394 (8) | 0.3039 (5) | 0.060 (3) | 0.579 (6) |
C35A | 0.7525 (15) | −0.0962 (12) | 0.2578 (8) | 0.070 (3) | 0.421 (6) |
C36 | 0.6293 (12) | −0.1364 (8) | 0.2904 (7) | 0.084 (3) | 0.579 (6) |
C36A | 0.5800 (12) | −0.1131 (11) | 0.3649 (9) | 0.068 (4) | 0.421 (6) |
F1 | 0.0786 (3) | 0.1645 (2) | 0.55023 (19) | 0.0654 (10) | |
F2 | 0.0693 (3) | 0.4234 (2) | 0.5525 (2) | 0.0898 (16) | |
F3 | −0.0877 (2) | 0.2619 (2) | 0.54952 (15) | 0.0485 (8) | |
F4 | 0.0922 (3) | 0.3122 (4) | 0.64204 (16) | 0.1022 (16) | |
F5 | 0.2353 (3) | 0.3262 (2) | 0.55336 (18) | 0.0633 (10) | |
F6 | 0.0548 (3) | 0.2751 (3) | 0.46073 (14) | 0.0690 (11) | |
H2 | 0.50370 | 0.33200 | 0.49020 | 0.0450* | |
H3 | 0.71700 | 0.44220 | 0.45760 | 0.0500* | |
H5 | 0.28840 | 0.17010 | 0.46450 | 0.0450* | |
H6 | 0.11220 | 0.00480 | 0.43420 | 0.0550* | |
H7 | 0.11620 | −0.13360 | 0.33050 | 0.0480* | |
H8 | 0.28980 | −0.10080 | 0.25680 | 0.0380* | |
H9A | 0.89090 | 0.34820 | 0.36050 | 0.0520* | |
H9B | 0.81550 | 0.42970 | 0.31560 | 0.0520* | |
H11 | 0.97760 | 0.35610 | 0.21010 | 0.0530* | |
H12 | 0.90290 | 0.20580 | 0.09660 | 0.0520* | |
H14 | 0.75060 | 0.01550 | 0.02150 | 0.0500* | |
H15 | 0.59760 | −0.15570 | −0.03330 | 0.0570* | |
H16 | 0.41260 | −0.22700 | 0.02780 | 0.0530* | |
H17 | 0.38620 | −0.12690 | 0.14350 | 0.0410* | |
H19 | 0.11650 | 0.15230 | 0.10320 | 0.0320* | |
H20 | 0.25060 | 0.03360 | 0.16640 | 0.0300* | |
H22 | 0.40470 | 0.39570 | 0.03250 | 0.0440* | |
H23 | 0.34260 | 0.55460 | −0.01390 | 0.0560* | |
H24 | 0.16650 | 0.62360 | 0.03420 | 0.0560* | |
H25 | 0.05070 | 0.53020 | 0.11930 | 0.0600* | |
H27 | 0.78460 | 0.54810 | 0.16980 | 0.0610* | |
H28 | 0.66120 | 0.63230 | 0.26310 | 0.0660* | |
H30 | 0.43060 | 0.65490 | 0.27860 | 0.0830* | |
H31 | 0.25350 | 0.67040 | 0.35040 | 0.1000* | |
H32 | 0.13630 | 0.51060 | 0.39440 | 0.0770* | |
H33 | 0.19990 | 0.34140 | 0.36750 | 0.0640* | |
H34A | 0.61020 | 0.01900 | 0.43680 | 0.1000* | 0.579 (6) |
H34B | 0.73820 | 0.12140 | 0.43610 | 0.1000* | 0.579 (6) |
H34C | 0.76110 | −0.00360 | 0.44270 | 0.1000* | 0.579 (6) |
H34D | 0.84830 | 0.01250 | 0.41250 | 0.1090* | 0.421 (6) |
H34E | 0.76890 | 0.11080 | 0.43230 | 0.1090* | 0.421 (6) |
H34F | 0.87780 | 0.12540 | 0.37380 | 0.1090* | 0.421 (6) |
H35A | 0.91090 | −0.00740 | 0.33330 | 0.0910* | 0.579 (6) |
H35B | 0.90340 | 0.12020 | 0.32300 | 0.0910* | 0.579 (6) |
H35C | 0.87080 | 0.02250 | 0.24930 | 0.0910* | 0.579 (6) |
H35D | 0.79260 | −0.14240 | 0.29170 | 0.1050* | 0.421 (6) |
H35E | 0.82360 | −0.05490 | 0.23220 | 0.1050* | 0.421 (6) |
H35F | 0.68020 | −0.14580 | 0.21890 | 0.1050* | 0.421 (6) |
H36A | 0.68150 | −0.17290 | 0.32610 | 0.1250* | 0.579 (6) |
H36B | 0.64650 | −0.15790 | 0.23790 | 0.1250* | 0.579 (6) |
H36C | 0.53150 | −0.16130 | 0.29270 | 0.1250* | 0.579 (6) |
H36D | 0.64310 | −0.15750 | 0.38470 | 0.1020* | 0.421 (6) |
H36E | 0.50630 | −0.16310 | 0.32700 | 0.1020* | 0.421 (6) |
H36F | 0.54100 | −0.07890 | 0.40750 | 0.1020* | 0.421 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0148 (3) | 0.0302 (3) | 0.0199 (3) | 0.0069 (2) | 0.0007 (2) | −0.0004 (2) |
P1 | 0.0286 (6) | 0.0484 (7) | 0.0281 (5) | 0.0186 (5) | −0.0030 (4) | 0.0041 (5) |
P3 | 0.0369 (6) | 0.0320 (6) | 0.0437 (6) | 0.0079 (5) | −0.0113 (5) | −0.0003 (5) |
P2 | 0.0304 (6) | 0.0307 (6) | 0.0344 (6) | 0.0011 (4) | 0.0095 (5) | 0.0010 (4) |
N1 | 0.0285 (17) | 0.0310 (18) | 0.0201 (15) | 0.0079 (14) | 0.0039 (13) | −0.0029 (13) |
N2 | 0.0251 (17) | 0.0367 (19) | 0.0273 (16) | −0.0037 (15) | −0.0022 (14) | −0.0006 (14) |
N3 | 0.0217 (16) | 0.0253 (17) | 0.0229 (15) | 0.0058 (13) | 0.0001 (13) | 0.0032 (13) |
N4 | 0.0134 (16) | 0.055 (2) | 0.0335 (18) | −0.0009 (15) | −0.0009 (14) | 0.0083 (16) |
N5 | 0.0195 (17) | 0.053 (2) | 0.0289 (17) | 0.0167 (16) | 0.0074 (14) | 0.0067 (16) |
N6 | 0.0237 (17) | 0.0366 (19) | 0.0220 (15) | 0.0190 (14) | 0.0016 (13) | 0.0013 (14) |
N7 | 0.0169 (15) | 0.0224 (16) | 0.0287 (16) | 0.0064 (12) | 0.0066 (13) | 0.0045 (13) |
F7 | 0.039 (3) | 0.075 (4) | 0.117 (6) | 0.006 (3) | 0.015 (4) | −0.031 (5) |
F7A | 0.123 (5) | 0.106 (5) | 0.083 (4) | 0.018 (5) | 0.051 (4) | 0.001 (4) |
F8 | 0.032 (3) | 0.056 (4) | 0.156 (8) | 0.014 (3) | −0.006 (5) | −0.010 (6) |
N8 | 0.0128 (14) | 0.0216 (16) | 0.0211 (14) | 0.0034 (12) | 0.0040 (12) | 0.0001 (12) |
F8A | 0.123 (5) | 0.109 (5) | 0.121 (5) | 0.003 (4) | 0.063 (4) | 0.024 (4) |
F9 | 0.054 (3) | 0.088 (5) | 0.091 (4) | 0.012 (3) | −0.013 (3) | −0.045 (4) |
N9 | 0.0306 (19) | 0.039 (2) | 0.052 (2) | 0.0187 (16) | 0.0179 (16) | 0.0180 (17) |
F9A | 0.035 (3) | 0.028 (3) | 0.119 (5) | 0.013 (2) | −0.008 (4) | 0.008 (3) |
N10 | 0.0231 (18) | 0.042 (2) | 0.050 (2) | 0.0039 (15) | 0.0119 (16) | 0.0090 (17) |
F10 | 0.132 (5) | 0.089 (4) | 0.110 (5) | 0.019 (4) | 0.006 (4) | 0.040 (4) |
F10A | 0.065 (5) | 0.087 (4) | 0.105 (6) | 0.014 (4) | −0.058 (4) | −0.007 (5) |
N11 | 0.0302 (19) | 0.0279 (19) | 0.050 (2) | −0.0011 (15) | 0.0080 (16) | −0.0049 (16) |
F11 | 0.058 (3) | 0.071 (5) | 0.086 (5) | 0.016 (3) | 0.002 (4) | −0.033 (4) |
F11A | 0.052 (4) | 0.036 (4) | 0.117 (7) | 0.001 (3) | 0.017 (5) | −0.022 (4) |
F12 | 0.098 (4) | 0.081 (4) | 0.126 (5) | 0.027 (3) | 0.023 (4) | 0.066 (4) |
N12 | 0.053 (2) | 0.054 (3) | 0.037 (2) | 0.014 (2) | 0.0098 (18) | 0.0047 (18) |
F12A | 0.084 (6) | 0.054 (4) | 0.123 (7) | 0.040 (4) | −0.052 (5) | 0.007 (5) |
C1 | 0.0193 (19) | 0.028 (2) | 0.0265 (19) | 0.0049 (16) | −0.0010 (15) | 0.0015 (16) |
C2 | 0.045 (3) | 0.037 (2) | 0.027 (2) | 0.007 (2) | 0.0045 (19) | −0.0051 (18) |
C3 | 0.050 (3) | 0.034 (2) | 0.029 (2) | 0.000 (2) | −0.005 (2) | −0.0093 (18) |
C4 | 0.025 (2) | 0.030 (2) | 0.0232 (18) | 0.0095 (16) | 0.0009 (16) | 0.0037 (16) |
C5 | 0.035 (2) | 0.053 (3) | 0.025 (2) | 0.014 (2) | 0.0085 (18) | 0.0043 (19) |
C6 | 0.033 (2) | 0.068 (3) | 0.036 (2) | 0.003 (2) | 0.0092 (19) | 0.019 (2) |
C7 | 0.033 (2) | 0.047 (3) | 0.036 (2) | −0.006 (2) | 0.0039 (19) | 0.015 (2) |
C8 | 0.032 (2) | 0.031 (2) | 0.029 (2) | 0.0028 (18) | −0.0009 (17) | 0.0065 (17) |
C9 | 0.030 (2) | 0.054 (3) | 0.034 (2) | −0.007 (2) | −0.0060 (19) | 0.004 (2) |
C10 | 0.0161 (19) | 0.049 (2) | 0.0220 (18) | 0.0097 (18) | 0.0001 (15) | 0.0063 (17) |
C11 | 0.014 (2) | 0.076 (3) | 0.045 (3) | 0.006 (2) | 0.0078 (19) | 0.021 (2) |
C12 | 0.020 (2) | 0.077 (3) | 0.041 (2) | 0.020 (2) | 0.0147 (19) | 0.020 (2) |
C13 | 0.030 (2) | 0.048 (3) | 0.028 (2) | 0.030 (2) | 0.0034 (18) | 0.0067 (18) |
C14 | 0.047 (3) | 0.060 (3) | 0.030 (2) | 0.038 (2) | 0.012 (2) | 0.008 (2) |
C15 | 0.071 (3) | 0.055 (3) | 0.029 (2) | 0.044 (3) | 0.009 (2) | 0.000 (2) |
C16 | 0.060 (3) | 0.041 (3) | 0.033 (2) | 0.027 (2) | −0.003 (2) | −0.0064 (19) |
C17 | 0.039 (2) | 0.034 (2) | 0.030 (2) | 0.0199 (19) | −0.0012 (18) | 0.0007 (18) |
C18 | 0.0177 (18) | 0.0223 (19) | 0.0213 (17) | 0.0039 (15) | 0.0076 (15) | −0.0007 (15) |
C19 | 0.0161 (18) | 0.024 (2) | 0.038 (2) | 0.0032 (15) | 0.0031 (16) | 0.0072 (17) |
C20 | 0.0188 (19) | 0.0214 (19) | 0.034 (2) | 0.0017 (15) | 0.0022 (16) | 0.0053 (16) |
C21 | 0.0213 (19) | 0.0234 (19) | 0.0287 (19) | 0.0051 (15) | 0.0076 (16) | 0.0048 (16) |
C22 | 0.030 (2) | 0.035 (2) | 0.049 (2) | 0.0105 (19) | 0.014 (2) | 0.011 (2) |
C23 | 0.045 (3) | 0.042 (3) | 0.059 (3) | 0.005 (2) | 0.018 (2) | 0.028 (2) |
C24 | 0.038 (3) | 0.037 (3) | 0.073 (3) | 0.015 (2) | 0.015 (2) | 0.026 (2) |
C25 | 0.042 (3) | 0.045 (3) | 0.079 (3) | 0.026 (2) | 0.020 (3) | 0.026 (3) |
C26 | 0.023 (2) | 0.027 (2) | 0.034 (2) | 0.0061 (16) | 0.0035 (17) | 0.0011 (16) |
C27 | 0.027 (2) | 0.040 (3) | 0.079 (3) | −0.006 (2) | 0.013 (2) | 0.008 (2) |
C28 | 0.035 (3) | 0.029 (2) | 0.090 (4) | −0.008 (2) | 0.009 (3) | −0.006 (2) |
C29 | 0.036 (2) | 0.031 (2) | 0.047 (2) | 0.0031 (19) | 0.008 (2) | −0.013 (2) |
C30 | 0.055 (3) | 0.030 (3) | 0.121 (5) | 0.006 (2) | 0.037 (3) | −0.009 (3) |
C31 | 0.072 (4) | 0.053 (4) | 0.123 (5) | 0.022 (3) | 0.038 (4) | −0.024 (4) |
C32 | 0.045 (3) | 0.083 (4) | 0.055 (3) | 0.008 (3) | 0.014 (2) | −0.023 (3) |
C33 | 0.051 (3) | 0.074 (4) | 0.036 (2) | 0.010 (3) | 0.014 (2) | 0.005 (2) |
C34 | 0.078 (6) | 0.100 (7) | 0.039 (4) | 0.055 (5) | 0.003 (4) | 0.026 (4) |
C34A | 0.063 (6) | 0.087 (7) | 0.070 (6) | 0.032 (6) | −0.017 (5) | 0.023 (6) |
C35 | 0.042 (4) | 0.089 (5) | 0.072 (5) | 0.046 (4) | 0.012 (4) | 0.040 (4) |
C35A | 0.072 (6) | 0.086 (6) | 0.073 (6) | 0.057 (5) | 0.004 (5) | 0.028 (5) |
C36 | 0.078 (6) | 0.059 (5) | 0.109 (7) | 0.024 (5) | −0.034 (5) | 0.029 (5) |
C36A | 0.048 (6) | 0.059 (6) | 0.108 (8) | 0.018 (5) | 0.002 (6) | 0.053 (7) |
F1 | 0.0556 (17) | 0.0430 (16) | 0.110 (2) | 0.0157 (13) | 0.0321 (17) | 0.0318 (16) |
F2 | 0.067 (2) | 0.0316 (16) | 0.176 (4) | 0.0073 (14) | 0.060 (2) | 0.0024 (19) |
F3 | 0.0311 (13) | 0.0480 (15) | 0.0651 (16) | 0.0049 (11) | 0.0147 (12) | 0.0041 (13) |
F4 | 0.073 (2) | 0.178 (4) | 0.0367 (16) | 0.005 (2) | 0.0046 (15) | −0.011 (2) |
F5 | 0.0311 (14) | 0.0582 (18) | 0.092 (2) | −0.0020 (12) | 0.0145 (14) | −0.0045 (15) |
F6 | 0.072 (2) | 0.101 (2) | 0.0359 (14) | 0.0151 (17) | 0.0152 (14) | 0.0188 (15) |
Fe1—P1 | 2.2179 (13) | C6—C7 | 1.377 (6) |
Fe1—N3 | 2.080 (3) | C7—C8 | 1.378 (6) |
Fe1—N6 | 2.067 (3) | C11—C12 | 1.337 (6) |
Fe1—N8 | 2.047 (3) | C13—C14 | 1.386 (5) |
Fe1—C1 | 1.818 (4) | C14—C15 | 1.369 (7) |
Fe1—C10 | 1.812 (4) | C15—C16 | 1.381 (7) |
P1—C34 | 1.813 (9) | C16—C17 | 1.384 (5) |
P1—C35 | 1.863 (9) | C18—C26 | 1.458 (5) |
P1—C36 | 1.697 (10) | C19—C20 | 1.345 (5) |
P1—C34A | 1.732 (14) | C21—C22 | 1.367 (5) |
P1—C35A | 1.854 (15) | C22—C23 | 1.386 (6) |
P1—C36A | 1.954 (14) | C23—C24 | 1.361 (7) |
P3—F7A | 1.454 (10) | C24—C25 | 1.358 (7) |
P3—F7 | 1.623 (9) | C27—C28 | 1.334 (7) |
P3—F8 | 1.536 (11) | C29—C30 | 1.359 (7) |
P3—F9 | 1.641 (7) | C30—C31 | 1.378 (9) |
P3—F10 | 1.669 (9) | C31—C32 | 1.368 (8) |
P3—F11 | 1.532 (9) | C32—C33 | 1.355 (8) |
P3—F12 | 1.458 (9) | C2—H2 | 0.9500 |
P3—F10A | 1.528 (11) | C3—H3 | 0.9500 |
P3—F8A | 1.632 (11) | C5—H5 | 0.9500 |
P3—F9A | 1.602 (7) | C6—H6 | 0.9500 |
P3—F11A | 1.575 (10) | C7—H7 | 0.9500 |
P3—F12A | 1.521 (15) | C8—H8 | 0.9500 |
P2—F3 | 1.584 (2) | C9—H9A | 0.9900 |
P2—F1 | 1.583 (3) | C9—H9B | 0.9900 |
P2—F2 | 1.582 (3) | C11—H11 | 0.9500 |
P2—F6 | 1.575 (3) | C12—H12 | 0.9500 |
P2—F4 | 1.574 (3) | C14—H14 | 0.9500 |
P2—F5 | 1.603 (3) | C15—H15 | 0.9500 |
N1—C1 | 1.354 (5) | C16—H16 | 0.9500 |
N1—C4 | 1.403 (5) | C17—H17 | 0.9500 |
N1—C2 | 1.398 (5) | C19—H19 | 0.9500 |
N2—C3 | 1.395 (5) | C20—H20 | 0.9500 |
N2—C9 | 1.456 (5) | C22—H22 | 0.9500 |
N2—C1 | 1.351 (5) | C23—H23 | 0.9500 |
N3—C4 | 1.357 (4) | C24—H24 | 0.9500 |
N3—C8 | 1.348 (5) | C25—H25 | 0.9500 |
N4—C9 | 1.462 (5) | C27—H27 | 0.9500 |
N4—C11 | 1.395 (5) | C28—H28 | 0.9500 |
N4—C10 | 1.355 (5) | C30—H30 | 0.9500 |
N5—C12 | 1.404 (6) | C31—H31 | 0.9500 |
N5—C10 | 1.365 (5) | C32—H32 | 0.9500 |
N5—C13 | 1.398 (6) | C33—H33 | 0.9500 |
N6—C17 | 1.348 (5) | C34—H34B | 0.9800 |
N6—C13 | 1.359 (5) | C34—H34A | 0.9800 |
N7—C21 | 1.443 (4) | C34—H34C | 0.9800 |
N7—C19 | 1.366 (5) | C34A—H34D | 0.9800 |
N7—C18 | 1.366 (4) | C34A—H34E | 0.9800 |
N8—C18 | 1.330 (4) | C34A—H34F | 0.9800 |
N8—C20 | 1.385 (4) | C35—H35C | 0.9800 |
N9—C21 | 1.312 (5) | C35—H35B | 0.9800 |
N9—C25 | 1.345 (6) | C35—H35A | 0.9800 |
N10—C26 | 1.321 (5) | C35A—H35F | 0.9800 |
N10—C27 | 1.381 (6) | C35A—H35E | 0.9800 |
N11—C29 | 1.428 (5) | C35A—H35D | 0.9800 |
N11—C26 | 1.375 (5) | C36—H36C | 0.9800 |
N11—C28 | 1.374 (6) | C36—H36B | 0.9800 |
N12—C29 | 1.336 (6) | C36—H36A | 0.9800 |
N12—C33 | 1.351 (6) | C36A—H36D | 0.9800 |
C2—C3 | 1.332 (6) | C36A—H36E | 0.9800 |
C4—C5 | 1.384 (6) | C36A—H36F | 0.9800 |
C5—C6 | 1.380 (6) | ||
P1—Fe1—N3 | 89.96 (8) | N6—C13—C14 | 123.7 (4) |
P1—Fe1—N6 | 89.56 (10) | N5—C13—N6 | 112.5 (3) |
P1—Fe1—N8 | 171.70 (8) | N5—C13—C14 | 123.8 (4) |
P1—Fe1—C1 | 91.85 (12) | C13—C14—C15 | 117.7 (4) |
P1—Fe1—C10 | 89.64 (13) | C14—C15—C16 | 120.4 (4) |
N3—Fe1—N6 | 114.09 (12) | C15—C16—C17 | 118.5 (4) |
N3—Fe1—N8 | 85.49 (11) | N6—C17—C16 | 122.9 (4) |
N3—Fe1—C1 | 79.63 (14) | N7—C18—C26 | 120.1 (3) |
N3—Fe1—C10 | 165.82 (14) | N7—C18—N8 | 110.5 (3) |
N6—Fe1—N8 | 85.98 (12) | N8—C18—C26 | 129.5 (3) |
N6—Fe1—C1 | 166.22 (16) | N7—C19—C20 | 106.4 (3) |
N6—Fe1—C10 | 80.08 (15) | N8—C20—C19 | 110.5 (3) |
N8—Fe1—C1 | 94.15 (14) | N7—C21—C22 | 120.1 (3) |
N8—Fe1—C10 | 96.47 (14) | N9—C21—C22 | 125.2 (4) |
C1—Fe1—C10 | 86.22 (17) | N7—C21—N9 | 114.7 (3) |
Fe1—P1—C34 | 114.2 (4) | C21—C22—C23 | 117.5 (4) |
Fe1—P1—C35 | 115.2 (3) | C22—C23—C24 | 118.8 (5) |
Fe1—P1—C36 | 115.4 (4) | C23—C24—C25 | 118.9 (5) |
Fe1—P1—C34A | 122.1 (5) | N9—C25—C24 | 123.9 (5) |
Fe1—P1—C35A | 118.5 (4) | N11—C26—C18 | 123.2 (3) |
Fe1—P1—C36A | 115.8 (4) | N10—C26—C18 | 124.7 (3) |
C34—P1—C35 | 98.6 (5) | N10—C26—N11 | 111.6 (3) |
C34—P1—C36 | 108.0 (5) | N10—C27—C28 | 111.2 (4) |
C35—P1—C36 | 103.5 (5) | N11—C28—C27 | 106.8 (4) |
C34A—P1—C35A | 104.7 (7) | N12—C29—C30 | 124.0 (4) |
C34A—P1—C36A | 98.7 (7) | N11—C29—N12 | 116.2 (4) |
C35A—P1—C36A | 91.5 (6) | N11—C29—C30 | 119.8 (4) |
F8A—P3—F11A | 87.4 (5) | C29—C30—C31 | 117.6 (5) |
F8A—P3—F12A | 90.8 (6) | C30—C31—C32 | 120.3 (5) |
F9A—P3—F10A | 90.9 (5) | C31—C32—C33 | 117.9 (5) |
F9A—P3—F11A | 170.3 (5) | N12—C33—C32 | 123.8 (5) |
F9A—P3—F12A | 88.7 (6) | N1—C2—H2 | 127.00 |
F10A—P3—F11A | 94.4 (6) | C3—C2—H2 | 127.00 |
F10A—P3—F12A | 177.5 (7) | C2—C3—H3 | 126.00 |
F11A—P3—F12A | 86.3 (7) | N2—C3—H3 | 126.00 |
F10—P3—F12 | 171.2 (5) | C4—C5—H5 | 121.00 |
F11—P3—F12 | 98.2 (5) | C6—C5—H5 | 121.00 |
F7—P3—F8 | 175.5 (6) | C7—C6—H6 | 120.00 |
F7—P3—F9 | 82.9 (4) | C5—C6—H6 | 120.00 |
F7—P3—F10 | 80.6 (5) | C6—C7—H7 | 121.00 |
F7—P3—F11 | 87.1 (5) | C8—C7—H7 | 121.00 |
F7—P3—F12 | 91.2 (5) | N3—C8—H8 | 118.00 |
F8—P3—F9 | 94.3 (5) | C7—C8—H8 | 118.00 |
F8—P3—F10 | 95.7 (6) | N2—C9—H9B | 109.00 |
F8—P3—F11 | 95.2 (6) | N2—C9—H9A | 109.00 |
F8—P3—F12 | 92.3 (6) | H9A—C9—H9B | 108.00 |
F9—P3—F10 | 84.9 (4) | N4—C9—H9A | 109.00 |
F9—P3—F11 | 166.7 (5) | N4—C9—H9B | 109.00 |
F9—P3—F12 | 90.7 (4) | N4—C11—H11 | 126.00 |
F10—P3—F11 | 84.9 (5) | C12—C11—H11 | 126.00 |
F8A—P3—F9A | 84.3 (5) | C11—C12—H12 | 127.00 |
F8A—P3—F10A | 91.7 (6) | N5—C12—H12 | 127.00 |
F7A—P3—F8A | 175.9 (6) | C13—C14—H14 | 121.00 |
F7A—P3—F9A | 92.5 (6) | C15—C14—H14 | 121.00 |
F7A—P3—F10A | 91.0 (6) | C16—C15—H15 | 120.00 |
F7A—P3—F11A | 95.5 (6) | C14—C15—H15 | 120.00 |
F7A—P3—F12A | 86.5 (6) | C15—C16—H16 | 121.00 |
F1—P2—F2 | 179.19 (18) | C17—C16—H16 | 121.00 |
F1—P2—F3 | 90.56 (15) | N6—C17—H17 | 119.00 |
F2—P2—F6 | 90.30 (19) | C16—C17—H17 | 118.00 |
F3—P2—F4 | 89.27 (16) | C20—C19—H19 | 127.00 |
F3—P2—F5 | 179.93 (17) | N7—C19—H19 | 127.00 |
F3—P2—F6 | 91.22 (16) | N8—C20—H20 | 125.00 |
F4—P2—F5 | 90.69 (17) | C19—C20—H20 | 125.00 |
F4—P2—F6 | 179.46 (18) | C21—C22—H22 | 121.00 |
F5—P2—F6 | 88.83 (17) | C23—C22—H22 | 121.00 |
F2—P2—F5 | 89.70 (15) | C22—C23—H23 | 121.00 |
F1—P2—F6 | 89.64 (18) | C24—C23—H23 | 121.00 |
F1—P2—F4 | 90.1 (2) | C23—C24—H24 | 121.00 |
F1—P2—F5 | 89.49 (15) | C25—C24—H24 | 121.00 |
F2—P2—F3 | 90.25 (15) | N9—C25—H25 | 118.00 |
F2—P2—F4 | 89.9 (2) | C24—C25—H25 | 118.00 |
C1—N1—C2 | 111.4 (3) | N10—C27—H27 | 124.00 |
C2—N1—C4 | 132.8 (3) | C28—C27—H27 | 124.00 |
C1—N1—C4 | 115.7 (3) | N11—C28—H28 | 127.00 |
C1—N2—C3 | 110.3 (3) | C27—C28—H28 | 127.00 |
C3—N2—C9 | 124.4 (4) | C31—C30—H30 | 121.00 |
C1—N2—C9 | 125.2 (3) | C29—C30—H30 | 121.00 |
C4—N3—C8 | 115.9 (3) | C32—C31—H31 | 120.00 |
Fe1—N3—C8 | 131.6 (2) | C30—C31—H31 | 120.00 |
Fe1—N3—C4 | 112.3 (2) | C33—C32—H32 | 121.00 |
C9—N4—C10 | 125.5 (3) | C31—C32—H32 | 121.00 |
C9—N4—C11 | 124.3 (3) | N12—C33—H33 | 118.00 |
C10—N4—C11 | 110.2 (3) | C32—C33—H33 | 118.00 |
C10—N5—C13 | 115.4 (3) | P1—C34—H34C | 109.00 |
C12—N5—C13 | 134.1 (3) | H34A—C34—H34B | 109.00 |
C10—N5—C12 | 110.3 (3) | P1—C34—H34A | 109.00 |
Fe1—N6—C13 | 112.4 (3) | P1—C34—H34B | 109.00 |
Fe1—N6—C17 | 130.8 (3) | H34A—C34—H34C | 110.00 |
C13—N6—C17 | 116.7 (3) | H34B—C34—H34C | 110.00 |
C18—N7—C19 | 107.5 (3) | P1—C34A—H34F | 109.00 |
C19—N7—C21 | 126.8 (3) | P1—C34A—H34D | 109.00 |
C18—N7—C21 | 125.7 (3) | P1—C34A—H34E | 109.00 |
Fe1—N8—C20 | 120.9 (2) | H34E—C34A—H34F | 110.00 |
Fe1—N8—C18 | 133.9 (2) | H34D—C34A—H34F | 109.00 |
C18—N8—C20 | 105.1 (3) | H34D—C34A—H34E | 110.00 |
C21—N9—C25 | 115.7 (4) | P1—C35—H35C | 109.00 |
C26—N10—C27 | 104.5 (3) | P1—C35—H35B | 109.00 |
C28—N11—C29 | 127.0 (4) | H35B—C35—H35C | 110.00 |
C26—N11—C28 | 105.9 (3) | H35A—C35—H35B | 109.00 |
C26—N11—C29 | 126.8 (4) | H35A—C35—H35C | 109.00 |
C29—N12—C33 | 116.4 (4) | P1—C35—H35A | 109.00 |
N1—C1—N2 | 104.6 (3) | P1—C35A—H35D | 109.00 |
Fe1—C1—N1 | 119.8 (3) | P1—C35A—H35E | 109.00 |
Fe1—C1—N2 | 135.6 (3) | P1—C35A—H35F | 109.00 |
N1—C2—C3 | 105.7 (3) | H35D—C35A—H35E | 109.00 |
N2—C3—C2 | 107.9 (4) | H35E—C35A—H35F | 109.00 |
N1—C4—N3 | 112.2 (3) | H35D—C35A—H35F | 110.00 |
N1—C4—C5 | 123.9 (3) | P1—C36—H36C | 109.00 |
N3—C4—C5 | 124.0 (4) | H36A—C36—H36B | 109.00 |
C4—C5—C6 | 117.7 (4) | P1—C36—H36B | 109.00 |
C5—C6—C7 | 120.0 (4) | H36B—C36—H36C | 110.00 |
C6—C7—C8 | 118.4 (4) | H36A—C36—H36C | 109.00 |
N3—C8—C7 | 124.0 (3) | P1—C36—H36A | 109.00 |
N2—C9—N4 | 111.8 (3) | H36E—C36A—H36F | 110.00 |
Fe1—C10—N5 | 119.5 (3) | P1—C36A—H36D | 109.00 |
Fe1—C10—N4 | 135.2 (3) | P1—C36A—H36E | 109.00 |
N4—C10—N5 | 105.3 (3) | P1—C36A—H36F | 109.00 |
N4—C11—C12 | 107.9 (4) | H36D—C36A—H36E | 109.00 |
N5—C12—C11 | 106.4 (4) | H36D—C36A—H36F | 110.00 |
N3—Fe1—P1—C34 | −55.4 (4) | C9—N4—C10—Fe1 | −4.1 (6) |
N6—Fe1—P1—C34 | −169.4 (4) | C9—N4—C11—C12 | −177.9 (4) |
C1—Fe1—P1—C34 | 24.3 (4) | C13—N5—C10—Fe1 | −2.9 (5) |
C10—Fe1—P1—C34 | 110.5 (4) | C12—N5—C10—N4 | −0.4 (4) |
N3—Fe1—P1—C35 | −168.5 (3) | C13—N5—C10—N4 | 175.3 (3) |
N6—Fe1—P1—C35 | 77.4 (3) | C12—N5—C10—Fe1 | −178.6 (3) |
C1—Fe1—P1—C35 | −88.9 (3) | C13—N5—C12—C11 | −174.1 (4) |
C10—Fe1—P1—C35 | −2.7 (3) | C10—N5—C13—N6 | 1.9 (5) |
N3—Fe1—P1—C36 | 70.8 (5) | C10—N5—C12—C11 | 0.5 (5) |
N6—Fe1—P1—C36 | −43.3 (5) | C12—N5—C13—C14 | −2.0 (7) |
C1—Fe1—P1—C36 | 150.4 (5) | C12—N5—C13—N6 | 176.3 (4) |
C10—Fe1—P1—C36 | −123.4 (5) | C10—N5—C13—C14 | −176.3 (4) |
N8—Fe1—C10—N5 | −82.7 (3) | Fe1—N6—C13—C14 | 177.9 (3) |
C1—Fe1—C10—N5 | −176.5 (3) | C17—N6—C13—N5 | −179.9 (3) |
C1—Fe1—N8—C20 | −127.3 (3) | C17—N6—C13—C14 | −1.6 (6) |
P1—Fe1—N3—C4 | 97.4 (2) | Fe1—N6—C13—N5 | −0.4 (4) |
N6—Fe1—N3—C4 | −173.1 (2) | C13—N6—C17—C16 | 0.8 (6) |
N8—Fe1—N3—C4 | −89.5 (2) | Fe1—N6—C17—C16 | −178.6 (3) |
C1—Fe1—N3—C4 | 5.6 (3) | C18—N7—C21—N9 | −120.2 (4) |
P1—Fe1—N3—C8 | −87.6 (3) | C18—N7—C21—C22 | 60.7 (5) |
N6—Fe1—N3—C8 | 1.9 (4) | C18—N7—C19—C20 | −1.2 (4) |
N8—Fe1—N3—C8 | 85.5 (3) | C19—N7—C18—C26 | −178.0 (3) |
C1—Fe1—N3—C8 | −179.5 (3) | C21—N7—C19—C20 | 179.0 (3) |
N3—Fe1—N8—C18 | 129.7 (3) | C19—N7—C21—N9 | 59.6 (5) |
N6—Fe1—N8—C18 | −115.8 (3) | C19—N7—C21—C22 | −119.5 (4) |
C1—Fe1—N8—C18 | 50.4 (3) | C19—N7—C18—N8 | 0.6 (4) |
C10—Fe1—N8—C18 | −36.2 (3) | C21—N7—C18—N8 | −179.6 (3) |
N3—Fe1—N8—C20 | −48.1 (3) | C21—N7—C18—C26 | 1.9 (5) |
N6—Fe1—N8—C20 | 66.5 (3) | C20—N8—C18—C26 | 178.6 (3) |
N6—Fe1—C10—N5 | 2.0 (3) | Fe1—N8—C18—C26 | 0.6 (6) |
P1—Fe1—C1—N2 | 87.4 (4) | Fe1—N8—C20—C19 | 177.4 (2) |
N3—Fe1—C1—N2 | 177.0 (4) | C20—N8—C18—N7 | 0.2 (4) |
P1—Fe1—N6—C13 | −90.6 (3) | Fe1—N8—C18—N7 | −177.8 (2) |
N3—Fe1—N6—C13 | 179.7 (3) | C18—N8—C20—C19 | −1.0 (4) |
N8—Fe1—N6—C13 | 96.4 (3) | C25—N9—C21—C22 | −0.8 (6) |
C10—Fe1—N6—C13 | −0.9 (3) | C25—N9—C21—N7 | −179.9 (4) |
P1—Fe1—N6—C17 | 88.9 (3) | C21—N9—C25—C24 | −0.8 (7) |
N3—Fe1—N6—C17 | −0.9 (4) | C26—N10—C27—C28 | −1.4 (5) |
C10—Fe1—N6—C17 | 178.6 (4) | C27—N10—C26—N11 | 1.1 (4) |
P1—Fe1—C10—N4 | −85.8 (4) | C27—N10—C26—C18 | 173.3 (4) |
N6—Fe1—C10—N4 | −175.5 (4) | C26—N11—C29—N12 | 35.1 (5) |
N8—Fe1—C10—N4 | 99.8 (4) | C28—N11—C26—N10 | −0.4 (5) |
C1—Fe1—C10—N4 | 6.0 (4) | C28—N11—C26—C18 | −172.8 (4) |
P1—Fe1—C10—N5 | 91.6 (3) | C26—N11—C28—C27 | −0.5 (5) |
C10—Fe1—C1—N1 | 177.1 (3) | C29—N11—C28—C27 | −174.8 (4) |
C10—Fe1—N8—C20 | 146.0 (3) | C26—N11—C29—C30 | −144.1 (5) |
N8—Fe1—N6—C17 | −84.1 (3) | C28—N11—C29—N12 | −151.7 (4) |
C10—Fe1—C1—N2 | −2.1 (4) | C28—N11—C29—C30 | 29.1 (7) |
N8—Fe1—C1—N1 | 80.9 (3) | C29—N11—C26—C18 | 1.6 (6) |
N8—Fe1—C1—N2 | −98.3 (4) | C29—N11—C26—N10 | 173.9 (4) |
P1—Fe1—C1—N1 | −93.4 (3) | C33—N12—C29—C30 | 1.0 (6) |
N3—Fe1—C1—N1 | −3.8 (3) | C33—N12—C29—N11 | −178.2 (3) |
C4—N1—C1—Fe1 | 1.4 (5) | C29—N12—C33—C32 | −1.6 (6) |
C4—N1—C2—C3 | 179.1 (4) | N1—C2—C3—N2 | −0.1 (5) |
C4—N1—C1—N2 | −179.2 (3) | N1—C4—C5—C6 | −178.4 (4) |
C2—N1—C4—C5 | 4.1 (7) | N3—C4—C5—C6 | 1.2 (6) |
C1—N1—C2—C3 | −0.1 (5) | C4—C5—C6—C7 | 0.4 (6) |
C2—N1—C1—N2 | 0.2 (4) | C5—C6—C7—C8 | −1.4 (6) |
C1—N1—C4—C5 | −176.8 (4) | C6—C7—C8—N3 | 0.9 (6) |
C2—N1—C4—N3 | −175.6 (4) | N4—C11—C12—N5 | −0.4 (5) |
C2—N1—C1—Fe1 | −179.3 (3) | N5—C13—C14—C15 | 179.4 (4) |
C1—N1—C4—N3 | 3.5 (5) | N6—C13—C14—C15 | 1.4 (7) |
C3—N2—C1—N1 | −0.2 (4) | C13—C14—C15—C16 | −0.2 (7) |
C3—N2—C1—Fe1 | 179.1 (3) | C14—C15—C16—C17 | −0.6 (7) |
C9—N2—C3—C2 | −176.9 (4) | C15—C16—C17—N6 | 0.3 (7) |
C3—N2—C9—N4 | −176.5 (4) | N7—C18—C26—N10 | −103.1 (4) |
C9—N2—C1—N1 | 176.8 (3) | N7—C18—C26—N11 | 68.2 (5) |
C1—N2—C3—C2 | 0.2 (5) | N8—C18—C26—N10 | 78.6 (5) |
C1—N2—C9—N4 | 6.9 (5) | N8—C18—C26—N11 | −110.0 (4) |
C9—N2—C1—Fe1 | −3.9 (6) | N7—C19—C20—N8 | 1.3 (4) |
Fe1—N3—C4—N1 | −6.2 (4) | N7—C21—C22—C23 | −180.0 (4) |
Fe1—N3—C4—C5 | 174.2 (3) | N9—C21—C22—C23 | 1.0 (6) |
C8—N3—C4—N1 | 178.0 (3) | C21—C22—C23—C24 | 0.4 (6) |
C8—N3—C4—C5 | −1.7 (5) | C22—C23—C24—C25 | −1.8 (7) |
Fe1—N3—C8—C7 | −174.3 (3) | C23—C24—C25—N9 | 2.1 (8) |
C4—N3—C8—C7 | 0.6 (5) | N10—C27—C28—N11 | 1.2 (6) |
C10—N4—C9—N2 | −3.4 (5) | N11—C29—C30—C31 | 179.4 (5) |
C9—N4—C10—N5 | 178.2 (3) | N12—C29—C30—C31 | 0.3 (8) |
C11—N4—C10—Fe1 | 177.9 (3) | C29—C30—C31—C32 | −1.0 (9) |
C11—N4—C10—N5 | 0.2 (4) | C30—C31—C32—C33 | 0.5 (9) |
C10—N4—C11—C12 | 0.1 (5) | C31—C32—C33—N12 | 0.8 (8) |
C11—N4—C9—N2 | 174.4 (4) |
Experimental details
Crystal data | |
Chemical formula | [Fe(C17H14N6)(C16H12N6)(C3H9P)](PF6)2 |
Mr | 1012.52 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 123 |
a, b, c (Å) | 10.1146 (4), 12.1591 (5), 17.7002 (7) |
α, β, γ (°) | 97.219 (2), 97.020 (2), 102.060 (2) |
V (Å3) | 2087.05 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.58 |
Crystal size (mm) | 0.25 × 0.22 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2012) |
Tmin, Tmax | 0.414, 0.745 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 52121, 7607, 5543 |
Rint | 0.095 |
(sin θ/λ)max (Å−1) | 0.604 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.135, 1.05 |
No. of reflections | 7607 |
No. of parameters | 666 |
No. of restraints | 120 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.75, −0.73 |
Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2012), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011), PLATON (Spek, 2009) and enCIFer (Allen et al., 2004).
Fe1—P1 | 2.2179 (13) | Fe1—N8 | 2.047 (3) |
Fe1—N3 | 2.080 (3) | Fe1—C1 | 1.818 (4) |
Fe1—N6 | 2.067 (3) | Fe1—C10 | 1.812 (4) |
P1—Fe1—N8 | 171.70 (8) | C1—Fe1—C10 | 86.22 (17) |
P1—Fe1—C1 | 91.85 (12) | Fe1—N3—C8 | 131.6 (2) |
P1—Fe1—C10 | 89.64 (13) | Fe1—N3—C4 | 112.3 (2) |
N3—Fe1—N6 | 114.09 (12) | Fe1—N6—C13 | 112.4 (3) |
N3—Fe1—C1 | 79.63 (14) | Fe1—N6—C17 | 130.8 (3) |
N6—Fe1—C10 | 80.08 (15) | Fe1—N8—C20 | 120.9 (2) |
N8—Fe1—C1 | 94.15 (14) | Fe1—N8—C18 | 133.9 (2) |
N8—Fe1—C10 | 96.47 (14) |