research communications
and magnetic properties of (tris{4-[1-(2-methoxyethyl)imidazol-2-yl]-3-azabut-3-enyl}amine)iron(II) bis(hexafluoridophosphate)
aDepartment of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street 64, Kyiv, 01601, Ukraine, bUkrOrgSyntez Ltd, Chervonotkatska St 67, Kyiv 02094, Ukraine, and cDepartment of Chemistry, University of Jyväskylä FIN-40014, Jyväskylä, Finland
*Correspondence e-mail: znovkat@yahoo.com
In the complex cation of the title compound, [Fe(C27H41N10O3)](PF6)2, the tripodal tris{4-[1-(2-methoxyethyl)imidazol-2-yl]-3-azabut-3-enyl}amine ligand is coordinated to an FeII ion through the nitrogen atoms of three imidazole and three imino groups. The Fe atom exhibits a distorted octahedral geometry. In the crystal, L and D antipodes are arranged in layers in the bc plane. Weak C⋯F and C—H⋯F/O contacts exist between the ligands of the complex cation and the PF6− anions, generating a three-dimensional network. At 120 K, the FeII ion is in a low-spin state, with an average Fe—N bond distance of 1.970 (2) Å. On heating, the FeII ion converts to the high-spin state, as demonstrated by measurements.
Keywords: crystal structure; spin crossover; spin transition.
CCDC reference: 1893862
1. Chemical context
One of the most investigated groups of switchable molecular materials are the pseudo-octahedral FeII spin-crossover (SCO) complexes, which can change between high-spin (HS, t2g4eg2) and low-spin (LS, t2g6eg0) electronic states on application of physicochemical stimuli. The LS-to-HS conversion involves an between the eg and t2g orbitals and is strongly coupled to structural changes in the coordination sphere of the FeII ions, affecting the Fe–ligand bond lengths and angles (Gütlich & Goodwin, 2004). The spin-state change is reversible and can be controlled, for example by the action of temperature, pressure or light. It is accompanied by a change in a number of physical properties, including colour, and NLO properties (König, 1991; Nakamoto et al., 2005; Bonhommeau et al., 2006, 2012). Tripod-based iron(II) complexes represent one of the well-studied classes of SCO complexes owing to the suitable ligand-field strength and readily achievable functionalization of their complex ligands (Hardie et al., 2004; Seredyuk et al., 2007; Klug et al., 2012; Hagiwara et al., 2014), particularly with aliphatic chains (Seredyuk et al., 2008a,b, 2013, 2014).
In this work, we report the synthesis, structure and magnetic properties of a new FeII complex based on the tripodal ligand tris{4-[1-(2-methoxyethyl)imidazol-2-yl]-3-azabut-3-enyl}amine, which can be crystallized in the presence of hexafluoridophosphate anions (Fig. 1).
2. Structural commentary
The L and D and eight PF6− counter-ions (on two crystallographically distinct sites) to balance the charge. In the complex cation, the FeII ion is wrapped by three 1-(2-methoxyethyl)-imidazol-2-ylimino moieties, defining a pseudo-octahedral [FeN6] coordination environment (Fig. 1). The average Fe—N bond length is 1.970 Å and is typical for the low-spin state of the FeII ion (Gütlich & Goodwin, 2004) (Table 1). The average trigonal distortion parameters, Φ = Σi24(60 − θi)/24 [where θi is the angle generated by superposition of two opposite faces of an octahedron (Chang et al., 1990)] and Σ = Σi12(|θi − 90|) [where θi is the deviation from 90° of the cis-N—Fe—N angles in the coordination sphere (Drew et al., 1995)] are 57.72 and 5.23°, respectively. These values are comparable to those reported previously for a similar low-spin compound with n-butyl substituents (Seredyuk et al., 2013). The capping tertiary nitrogen atom, N4, is situated at a distance of 3.375 (2) Å from the Fe atom and does not participate in coordination to the metal ion. Each of the methylene groups of the 2-methoxyethyl substituents directly attached to the imidazole moieties shows a gauche conformation, whilst the remaining methylene groups are in a trans conformation.
of the title compound contains two pairs of crystallographically identical complex cations of
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3. Supramolecular features
Supramolecular interactions occur between the complex cations and PF6− anions, with van der Waals contacts, C⋯F, lying in the range 2.934 (2)–3.137 (2) Å, linking the ions into two-dimensional layers running parallel to [011] (Fig. 2). These contacts are observed mostly for the carbon atoms belonging to the imidazole moieties of the ligand (Table 2). In addition, there are numerous C—H⋯F and C—H⋯O contacts between the complex cations and anions, extending the into a three-dimensional supramolecular network.
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4. Magnetic properties
Variable-temperature −1 between 150 and 300 K, is shown in Fig. 3 in the form of χMT vs T (χM is the molar and T is the temperature). At 300 K, the χMT value is close to 1.8 cm3 K mol−1, displaying at this temperature an incomplete transition of the FeII ion to the paramagnetic high-spin state (S = 2). On cooling, a gradual decrease of χMT value down to 0.07 cm3 K mol−1 is observed corresponding to an almost compete transformation to the diamagnetic low-spin state (S = 0). This corroborates well with the observed short average Fe—N bond length at 120 K and identifies the low-spin state of the central iron(II) ion.
measurements were performed on single crystals (20 mg) of the title compound using a Quantum Design MPMS2 superconducting quantum interference device (SQUID) susceptometer operating at 1 T in the temperature range 2–300 K. Experimental susceptibilities were corrected for the diamagnetism of the holder (gelatine capsule) and of the constituent atoms by the application of Pascal's constants. The magnetic behaviour of the compound recorded at 1 K min5. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.39, update November 2017; Groom et al., 2016) for complexes containing the FeII ion wrapped by a tripodal ligand with a tris{imidazol-2-yl-3-azabut-3-enyl}amine fragment yielded 29 hits, for which the Fe—N bond lengths lie in the ranges 1.926–2.016 and 2.151–2.286 Å for the low-spin and high-spin spin states of the FeII ion, respectively.
6. Synthesis and crystallization
A filtered solution of FeCl2·4H2O (0.043 g, 0.21 mmol) in absolute ethanol (5 mL) was added dropwise to a boiling solution of 1-(2-methoxyethyl)imidazole-2-carbaldehyde (0.10 g, 0.65 mmol), tris(2-ethanolamine)amine (0.031 g, 0.21 mmol) and [NBu4]PF6 (0.17 g, 0.43 mmol) in 5 ml of absolute ethanol. The resulting dark red–purple solution was stirred for 5 min. After standing for several days under ambient conditions, well-shaped red needles of the title compound were formed. Elemental analysis for C27H41F12FeN10O3P2 (found): C, 36.58, H, 4.98, N, 15.55%; (calculated): C, 36.77, H, 4.85, N, 15.32.
7. Refinement
Crystal data, data collection and structure . Hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.95–0.99 Å and Uiso(H) = 1.2–1.5Ueq(parent atom). The highest peak is located 1.21 Å from atom C24 and the deepest hole is located 0.65 Å from atom P2.
details are summarized in Table 3Supporting information
CCDC reference: 1893862
https://doi.org/10.1107/S2056989019001531/cq2029sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019001531/cq2029Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019001531/cq2029Isup3.cdx
Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).[Fe(C27H41N10O3)](PF6)2 | F(000) = 1844 |
Mr = 899.49 | Dx = 1.627 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 15.82801 (19) Å | Cell parameters from 25415 reflections |
b = 14.36708 (15) Å | θ = 4.1–76.3° |
c = 17.4210 (2) Å | µ = 5.10 mm−1 |
β = 112.0778 (13)° | T = 120 K |
V = 3671.09 (8) Å3 | Needle, red |
Z = 4 | 0.39 × 0.04 × 0.02 mm |
Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer | 7717 independent reflections |
Radiation source: micro-source | 6787 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.071 |
Detector resolution: 10.3953 pixels mm-1 | θmax = 76.6°, θmin = 3.0° |
φ scans and ω scans with κ offset | h = −19→19 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −15→18 |
Tmin = 0.565, Tmax = 1.000 | l = −21→21 |
58436 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0673P)2 + 4.9233P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
7717 reflections | Δρmax = 1.43 e Å−3 |
499 parameters | Δρmin = −0.62 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.21730 (2) | 0.13001 (3) | 0.05119 (2) | 0.01414 (10) | |
O1 | 0.39620 (14) | −0.06399 (16) | −0.08365 (13) | 0.0315 (5) | |
O2 | −0.14217 (15) | 0.43315 (15) | −0.14865 (12) | 0.0292 (4) | |
O3 | 0.37325 (18) | 0.45880 (18) | −0.02627 (15) | 0.0404 (5) | |
N1 | 0.18253 (14) | 0.04448 (15) | −0.04284 (13) | 0.0176 (4) | |
N2 | 0.21644 (14) | −0.08197 (16) | −0.09714 (13) | 0.0193 (4) | |
N3 | 0.29591 (13) | 0.02238 (15) | 0.10600 (12) | 0.0160 (4) | |
N4 | 0.24016 (15) | 0.07020 (16) | 0.24537 (13) | 0.0211 (4) | |
N5 | 0.27060 (14) | 0.22006 (15) | 0.14262 (12) | 0.0171 (4) | |
N6 | 0.10842 (14) | 0.09446 (15) | 0.07388 (13) | 0.0179 (4) | |
N7 | 0.13194 (14) | 0.22565 (15) | −0.01479 (13) | 0.0176 (4) | |
N8 | −0.00982 (14) | 0.27774 (16) | −0.06646 (13) | 0.0198 (4) | |
N9 | 0.31665 (14) | 0.17875 (15) | 0.02162 (13) | 0.0175 (4) | |
N10 | 0.42701 (15) | 0.28182 (16) | 0.04425 (14) | 0.0208 (4) | |
C1 | 0.13063 (17) | 0.04344 (19) | −0.12578 (15) | 0.0212 (5) | |
H1 | 0.0872 | 0.0893 | −0.1549 | 0.025* | |
C2 | 0.15162 (18) | −0.0345 (2) | −0.15976 (15) | 0.0220 (5) | |
H2 | 0.1259 | −0.0524 | −0.2164 | 0.026* | |
C3 | 0.26895 (18) | −0.16235 (19) | −0.10707 (17) | 0.0233 (5) | |
H3A | 0.2273 | −0.2075 | −0.1460 | 0.028* | |
H3B | 0.2989 | −0.1937 | −0.0530 | 0.028* | |
C4 | 0.34030 (19) | −0.1311 (2) | −0.13980 (17) | 0.0258 (6) | |
H4A | 0.3775 | −0.1848 | −0.1439 | 0.031* | |
H4B | 0.3107 | −0.1034 | −0.1956 | 0.031* | |
C5 | 0.4613 (2) | −0.0253 (2) | −0.1123 (2) | 0.0354 (7) | |
H5A | 0.4299 | 0.0035 | −0.1667 | 0.053* | |
H5B | 0.5018 | −0.0746 | −0.1172 | 0.053* | |
H5C | 0.4973 | 0.0219 | −0.0730 | 0.053* | |
C6 | 0.23381 (16) | −0.03225 (18) | −0.02678 (15) | 0.0174 (5) | |
C7 | 0.29764 (16) | −0.04447 (18) | 0.05679 (15) | 0.0178 (5) | |
H7 | 0.3373 | −0.0966 | 0.0742 | 0.021* | |
C8 | 0.35865 (17) | 0.01820 (19) | 0.19243 (15) | 0.0192 (5) | |
H8A | 0.3928 | 0.0775 | 0.2074 | 0.023* | |
H8B | 0.4032 | −0.0325 | 0.1991 | 0.023* | |
C9 | 0.30844 (18) | 0.00118 (19) | 0.25133 (15) | 0.0208 (5) | |
H9A | 0.2789 | −0.0607 | 0.2392 | 0.025* | |
H9B | 0.3537 | −0.0001 | 0.3090 | 0.025* | |
C10 | 0.14596 (18) | 0.0435 (2) | 0.21910 (16) | 0.0235 (5) | |
H10A | 0.1111 | 0.0956 | 0.2301 | 0.028* | |
H10B | 0.1411 | −0.0103 | 0.2527 | 0.028* | |
C11 | 0.10253 (17) | 0.01741 (19) | 0.12726 (16) | 0.0220 (5) | |
H11A | 0.1339 | −0.0379 | 0.1167 | 0.026* | |
H11B | 0.0377 | 0.0010 | 0.1133 | 0.026* | |
C12 | 0.03435 (17) | 0.13940 (18) | 0.03302 (15) | 0.0185 (5) | |
H12 | −0.0230 | 0.1251 | 0.0358 | 0.022* | |
C13 | 0.04749 (17) | 0.21344 (18) | −0.01724 (15) | 0.0186 (5) | |
C14 | −0.10876 (17) | 0.2835 (2) | −0.08629 (17) | 0.0237 (5) | |
H14A | −0.1247 | 0.2420 | −0.0484 | 0.028* | |
H14B | −0.1415 | 0.2607 | −0.1435 | 0.028* | |
C15 | −0.14067 (18) | 0.3809 (2) | −0.07905 (17) | 0.0240 (5) | |
H15A | −0.2024 | 0.3789 | −0.0773 | 0.029* | |
H15B | −0.0988 | 0.4103 | −0.0274 | 0.029* | |
C16 | −0.1742 (3) | 0.5244 (2) | −0.1468 (2) | 0.0396 (8) | |
H16A | −0.1724 | 0.5595 | −0.1944 | 0.059* | |
H16B | −0.1355 | 0.5552 | −0.0954 | 0.059* | |
H16C | −0.2371 | 0.5220 | −0.1493 | 0.059* | |
C17 | 0.04125 (18) | 0.3342 (2) | −0.09604 (16) | 0.0227 (5) | |
H17 | 0.0200 | 0.3858 | −0.1322 | 0.027* | |
C18 | 0.12892 (18) | 0.30127 (19) | −0.06317 (16) | 0.0211 (5) | |
H18 | 0.1795 | 0.3270 | −0.0726 | 0.025* | |
C19 | 0.26791 (18) | 0.16265 (19) | 0.27611 (15) | 0.0219 (5) | |
H19A | 0.3352 | 0.1641 | 0.3033 | 0.026* | |
H19B | 0.2426 | 0.1771 | 0.3188 | 0.026* | |
C20 | 0.23784 (18) | 0.23851 (19) | 0.20961 (16) | 0.0208 (5) | |
H20A | 0.1704 | 0.2422 | 0.1862 | 0.025* | |
H20B | 0.2617 | 0.2994 | 0.2353 | 0.025* | |
C21 | 0.33576 (17) | 0.27120 (18) | 0.13860 (15) | 0.0187 (5) | |
H21 | 0.3638 | 0.3194 | 0.1771 | 0.022* | |
C22 | 0.36201 (17) | 0.24818 (18) | 0.06987 (15) | 0.0181 (5) | |
C23 | 0.48204 (19) | 0.3653 (2) | 0.07504 (19) | 0.0286 (6) | |
H23A | 0.5271 | 0.3709 | 0.0483 | 0.034* | |
H23B | 0.5161 | 0.3593 | 0.1355 | 0.034* | |
C24 | 0.4245 (2) | 0.4521 (2) | 0.0580 (2) | 0.0361 (7) | |
H24 | 0.4234 | 0.4956 | 0.0987 | 0.043* | |
C25 | 0.2978 (2) | 0.5214 (3) | −0.0437 (2) | 0.0400 (8) | |
H25A | 0.2640 | 0.5246 | −0.1037 | 0.060* | |
H25B | 0.3204 | 0.5835 | −0.0226 | 0.060* | |
H25C | 0.2573 | 0.4989 | −0.0168 | 0.060* | |
C26 | 0.42143 (18) | 0.2312 (2) | −0.02411 (17) | 0.0246 (5) | |
H26 | 0.4579 | 0.2393 | −0.0562 | 0.030* | |
C27 | 0.35384 (18) | 0.1669 (2) | −0.03755 (16) | 0.0219 (5) | |
H27 | 0.3356 | 0.1217 | −0.0805 | 0.026* | |
P1 | 0.42153 (4) | 0.71698 (5) | 0.17349 (4) | 0.02010 (15) | |
F1 | 0.47941 (12) | 0.70753 (14) | 0.27046 (10) | 0.0325 (4) | |
F2 | 0.36482 (15) | 0.72759 (15) | 0.07629 (11) | 0.0449 (5) | |
F3 | 0.49897 (13) | 0.66092 (13) | 0.15446 (12) | 0.0343 (4) | |
F4 | 0.37056 (12) | 0.62183 (12) | 0.17462 (11) | 0.0304 (4) | |
F5 | 0.34493 (13) | 0.77432 (14) | 0.19246 (13) | 0.0405 (5) | |
F6 | 0.47373 (13) | 0.81263 (12) | 0.17197 (12) | 0.0356 (4) | |
P2 | 0.03848 (5) | 0.82009 (5) | 0.32494 (4) | 0.02474 (16) | |
F7 | 0.01914 (14) | 0.92862 (13) | 0.30856 (12) | 0.0368 (4) | |
F8 | 0.05638 (15) | 0.71109 (14) | 0.34195 (15) | 0.0481 (5) | |
F9 | 0.08112 (16) | 0.81600 (16) | 0.25507 (14) | 0.0491 (6) | |
F10 | 0.13629 (13) | 0.84253 (17) | 0.39345 (14) | 0.0483 (5) | |
F11 | −0.00539 (13) | 0.82390 (15) | 0.39448 (11) | 0.0378 (4) | |
F12 | −0.05994 (12) | 0.79688 (14) | 0.25731 (10) | 0.0337 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01229 (17) | 0.01787 (19) | 0.01052 (18) | 0.00178 (14) | 0.00231 (13) | 0.00087 (14) |
O1 | 0.0251 (10) | 0.0421 (12) | 0.0297 (11) | −0.0081 (9) | 0.0130 (8) | −0.0144 (9) |
O2 | 0.0355 (11) | 0.0300 (11) | 0.0248 (10) | 0.0132 (9) | 0.0143 (9) | 0.0101 (8) |
O3 | 0.0493 (14) | 0.0407 (13) | 0.0338 (12) | 0.0089 (11) | 0.0186 (11) | 0.0024 (10) |
N1 | 0.0162 (9) | 0.0205 (10) | 0.0129 (9) | 0.0023 (8) | 0.0019 (8) | 0.0024 (8) |
N2 | 0.0185 (10) | 0.0237 (11) | 0.0139 (10) | 0.0000 (8) | 0.0042 (8) | −0.0036 (8) |
N3 | 0.0140 (9) | 0.0208 (10) | 0.0111 (9) | −0.0005 (8) | 0.0023 (7) | 0.0007 (8) |
N4 | 0.0187 (10) | 0.0247 (11) | 0.0173 (10) | 0.0005 (8) | 0.0038 (8) | 0.0004 (9) |
N5 | 0.0172 (9) | 0.0201 (10) | 0.0130 (9) | 0.0044 (8) | 0.0045 (8) | 0.0016 (8) |
N6 | 0.0176 (9) | 0.0208 (10) | 0.0140 (9) | −0.0007 (8) | 0.0044 (8) | −0.0003 (8) |
N7 | 0.0170 (10) | 0.0211 (10) | 0.0134 (9) | 0.0018 (8) | 0.0044 (8) | 0.0005 (8) |
N8 | 0.0165 (10) | 0.0250 (11) | 0.0145 (10) | 0.0051 (8) | 0.0020 (8) | 0.0022 (8) |
N9 | 0.0170 (9) | 0.0212 (10) | 0.0137 (9) | 0.0045 (8) | 0.0052 (8) | 0.0026 (8) |
N10 | 0.0181 (10) | 0.0239 (11) | 0.0199 (10) | −0.0006 (8) | 0.0064 (8) | 0.0032 (9) |
C1 | 0.0177 (11) | 0.0264 (13) | 0.0135 (11) | −0.0011 (10) | −0.0009 (9) | 0.0013 (10) |
C2 | 0.0213 (12) | 0.0278 (13) | 0.0118 (11) | −0.0021 (10) | 0.0003 (9) | −0.0004 (10) |
C3 | 0.0246 (13) | 0.0250 (13) | 0.0193 (12) | 0.0028 (10) | 0.0070 (10) | −0.0043 (10) |
C4 | 0.0257 (13) | 0.0315 (15) | 0.0206 (13) | 0.0000 (11) | 0.0093 (11) | −0.0071 (11) |
C5 | 0.0286 (14) | 0.0434 (18) | 0.0387 (17) | −0.0051 (13) | 0.0177 (13) | −0.0081 (14) |
C6 | 0.0145 (10) | 0.0225 (12) | 0.0137 (11) | 0.0003 (9) | 0.0035 (9) | 0.0006 (9) |
C7 | 0.0158 (10) | 0.0210 (12) | 0.0146 (11) | 0.0007 (9) | 0.0036 (9) | −0.0002 (9) |
C8 | 0.0181 (11) | 0.0245 (12) | 0.0114 (11) | 0.0039 (9) | 0.0016 (9) | 0.0009 (9) |
C9 | 0.0227 (12) | 0.0257 (13) | 0.0115 (11) | 0.0031 (10) | 0.0035 (9) | 0.0040 (9) |
C10 | 0.0200 (12) | 0.0318 (14) | 0.0185 (12) | −0.0013 (10) | 0.0072 (10) | 0.0055 (11) |
C11 | 0.0189 (11) | 0.0224 (12) | 0.0230 (13) | −0.0039 (10) | 0.0059 (10) | 0.0049 (10) |
C12 | 0.0147 (11) | 0.0236 (12) | 0.0146 (11) | 0.0005 (9) | 0.0024 (9) | −0.0012 (9) |
C13 | 0.0166 (11) | 0.0221 (12) | 0.0141 (11) | 0.0026 (9) | 0.0024 (9) | −0.0013 (9) |
C14 | 0.0139 (11) | 0.0291 (14) | 0.0226 (13) | 0.0041 (10) | 0.0007 (9) | 0.0045 (11) |
C15 | 0.0210 (12) | 0.0310 (14) | 0.0187 (12) | 0.0076 (10) | 0.0060 (10) | 0.0055 (11) |
C16 | 0.0484 (19) | 0.0282 (16) | 0.050 (2) | 0.0149 (14) | 0.0279 (16) | 0.0110 (14) |
C17 | 0.0243 (13) | 0.0268 (13) | 0.0158 (12) | 0.0050 (10) | 0.0064 (10) | 0.0061 (10) |
C18 | 0.0210 (12) | 0.0251 (13) | 0.0164 (11) | 0.0028 (10) | 0.0061 (9) | 0.0032 (10) |
C19 | 0.0260 (12) | 0.0268 (13) | 0.0138 (11) | −0.0009 (10) | 0.0085 (10) | −0.0022 (10) |
C20 | 0.0237 (12) | 0.0232 (13) | 0.0181 (12) | 0.0014 (10) | 0.0109 (10) | −0.0030 (10) |
C21 | 0.0180 (11) | 0.0207 (12) | 0.0153 (11) | 0.0026 (9) | 0.0039 (9) | 0.0006 (9) |
C22 | 0.0157 (11) | 0.0212 (12) | 0.0159 (11) | 0.0022 (9) | 0.0044 (9) | 0.0031 (9) |
C23 | 0.0236 (13) | 0.0311 (15) | 0.0293 (14) | −0.0089 (11) | 0.0078 (11) | 0.0017 (12) |
C24 | 0.0379 (16) | 0.0291 (15) | 0.0367 (17) | −0.0025 (13) | 0.0088 (14) | 0.0015 (13) |
C25 | 0.0394 (17) | 0.0387 (18) | 0.0374 (18) | 0.0091 (14) | 0.0094 (14) | −0.0064 (14) |
C26 | 0.0224 (12) | 0.0323 (15) | 0.0212 (13) | 0.0024 (11) | 0.0104 (10) | 0.0048 (11) |
C27 | 0.0233 (12) | 0.0293 (14) | 0.0149 (11) | 0.0026 (10) | 0.0094 (10) | 0.0009 (10) |
P1 | 0.0189 (3) | 0.0224 (3) | 0.0168 (3) | 0.0011 (2) | 0.0042 (2) | 0.0028 (2) |
F1 | 0.0279 (8) | 0.0445 (10) | 0.0181 (8) | −0.0065 (7) | 0.0004 (6) | 0.0019 (7) |
F2 | 0.0534 (12) | 0.0462 (12) | 0.0196 (9) | 0.0020 (10) | −0.0038 (8) | 0.0091 (8) |
F3 | 0.0359 (9) | 0.0329 (9) | 0.0426 (10) | 0.0074 (8) | 0.0244 (8) | 0.0055 (8) |
F4 | 0.0274 (8) | 0.0296 (9) | 0.0299 (9) | −0.0083 (7) | 0.0058 (7) | 0.0008 (7) |
F5 | 0.0313 (9) | 0.0393 (10) | 0.0544 (12) | 0.0089 (8) | 0.0201 (9) | −0.0018 (9) |
F6 | 0.0390 (10) | 0.0236 (8) | 0.0458 (11) | −0.0041 (7) | 0.0176 (8) | 0.0052 (8) |
P2 | 0.0239 (3) | 0.0271 (4) | 0.0206 (3) | −0.0021 (3) | 0.0054 (3) | 0.0010 (3) |
F7 | 0.0443 (10) | 0.0284 (9) | 0.0430 (10) | −0.0032 (8) | 0.0224 (9) | 0.0016 (8) |
F8 | 0.0415 (11) | 0.0326 (10) | 0.0684 (15) | 0.0070 (8) | 0.0184 (10) | 0.0106 (10) |
F9 | 0.0595 (13) | 0.0526 (13) | 0.0541 (13) | −0.0195 (10) | 0.0431 (11) | −0.0200 (10) |
F10 | 0.0242 (9) | 0.0645 (14) | 0.0450 (12) | −0.0050 (9) | 0.0002 (8) | −0.0091 (10) |
F11 | 0.0395 (10) | 0.0535 (12) | 0.0204 (8) | −0.0055 (9) | 0.0112 (7) | 0.0039 (8) |
F12 | 0.0313 (9) | 0.0427 (10) | 0.0227 (8) | −0.0081 (8) | 0.0051 (7) | 0.0015 (7) |
Fe1—N1 | 1.954 (2) | C8—H8B | 0.9900 |
Fe1—N9 | 1.959 (2) | C9—H9A | 0.9900 |
Fe1—N7 | 1.967 (2) | C9—H9B | 0.9900 |
Fe1—N6 | 1.975 (2) | C10—C11 | 1.532 (4) |
Fe1—N5 | 1.978 (2) | C10—H10A | 0.9900 |
Fe1—N3 | 1.989 (2) | C10—H10B | 0.9900 |
O1—C5 | 1.417 (4) | C11—H11A | 0.9900 |
O1—C4 | 1.421 (3) | C11—H11B | 0.9900 |
O2—C16 | 1.411 (4) | C12—C13 | 1.442 (4) |
O2—C15 | 1.419 (3) | C12—H12 | 0.9500 |
O3—C24 | 1.388 (4) | C14—C15 | 1.509 (4) |
O3—C25 | 1.433 (4) | C14—H14A | 0.9900 |
N1—C6 | 1.335 (3) | C14—H14B | 0.9900 |
N1—C1 | 1.368 (3) | C15—H15A | 0.9900 |
N2—C6 | 1.355 (3) | C15—H15B | 0.9900 |
N2—C2 | 1.366 (3) | C16—H16A | 0.9800 |
N2—C3 | 1.471 (3) | C16—H16B | 0.9800 |
N3—C7 | 1.295 (3) | C16—H16C | 0.9800 |
N3—C8 | 1.461 (3) | C17—C18 | 1.371 (4) |
N4—C10 | 1.438 (3) | C17—H17 | 0.9500 |
N4—C19 | 1.438 (3) | C18—H18 | 0.9500 |
N4—C9 | 1.441 (3) | C19—C20 | 1.530 (4) |
N5—C21 | 1.289 (3) | C19—H19A | 0.9900 |
N5—C20 | 1.468 (3) | C19—H19B | 0.9900 |
N6—C12 | 1.293 (3) | C20—H20A | 0.9900 |
N6—C11 | 1.471 (3) | C20—H20B | 0.9900 |
N7—C13 | 1.333 (3) | C21—C22 | 1.446 (3) |
N7—C18 | 1.365 (3) | C21—H21 | 0.9500 |
N8—C13 | 1.351 (3) | C23—C24 | 1.506 (4) |
N8—C17 | 1.374 (4) | C23—H23A | 0.9900 |
N8—C14 | 1.474 (3) | C23—H23B | 0.9900 |
N9—C22 | 1.328 (3) | C24—H24 | 0.9500 |
N9—C27 | 1.376 (3) | C25—H25A | 0.9800 |
N10—C22 | 1.355 (3) | C25—H25B | 0.9800 |
N10—C26 | 1.370 (4) | C25—H25C | 0.9800 |
N10—C23 | 1.461 (3) | C26—C27 | 1.366 (4) |
C1—C2 | 1.365 (4) | C26—H26 | 0.9500 |
C1—H1 | 0.9500 | C27—H27 | 0.9500 |
C2—H2 | 0.9500 | P1—F4 | 1.5912 (17) |
C3—C4 | 1.512 (4) | P1—F1 | 1.5964 (17) |
C3—H3A | 0.9900 | P1—F2 | 1.5980 (18) |
C3—H3B | 0.9900 | P1—F5 | 1.5997 (19) |
C4—H4A | 0.9900 | P1—F3 | 1.6021 (18) |
C4—H4B | 0.9900 | P1—F6 | 1.6089 (18) |
C5—H5A | 0.9800 | P2—F10 | 1.593 (2) |
C5—H5B | 0.9800 | P2—F7 | 1.594 (2) |
C5—H5C | 0.9800 | P2—F12 | 1.5957 (18) |
C6—C7 | 1.437 (3) | P2—F8 | 1.599 (2) |
C7—H7 | 0.9500 | P2—F9 | 1.599 (2) |
C8—C9 | 1.535 (3) | P2—F11 | 1.6077 (19) |
C8—H8A | 0.9900 | ||
N1—Fe1—N9 | 90.30 (9) | H11A—C11—H11B | 108.0 |
N1—Fe1—N7 | 91.96 (9) | N6—C12—C13 | 113.3 (2) |
N9—Fe1—N7 | 92.27 (9) | N6—C12—H12 | 123.4 |
N1—Fe1—N6 | 90.75 (9) | C13—C12—H12 | 123.4 |
N9—Fe1—N6 | 172.91 (9) | N7—C13—N8 | 110.9 (2) |
N7—Fe1—N6 | 80.69 (9) | N7—C13—C12 | 116.7 (2) |
N1—Fe1—N5 | 170.70 (9) | N8—C13—C12 | 132.4 (2) |
N9—Fe1—N5 | 80.58 (9) | N8—C14—C15 | 113.1 (2) |
N7—Fe1—N5 | 90.29 (9) | N8—C14—H14A | 109.0 |
N6—Fe1—N5 | 98.53 (9) | C15—C14—H14A | 109.0 |
N1—Fe1—N3 | 80.90 (9) | N8—C14—H14B | 109.0 |
N9—Fe1—N3 | 89.14 (8) | C15—C14—H14B | 109.0 |
N7—Fe1—N3 | 172.73 (9) | H14A—C14—H14B | 107.8 |
N6—Fe1—N3 | 97.95 (9) | O2—C15—C14 | 108.6 (2) |
N5—Fe1—N3 | 96.98 (8) | O2—C15—H15A | 110.0 |
C5—O1—C4 | 111.7 (2) | C14—C15—H15A | 110.0 |
C16—O2—C15 | 111.3 (2) | O2—C15—H15B | 110.0 |
C24—O3—C25 | 112.1 (3) | C14—C15—H15B | 110.0 |
C6—N1—C1 | 106.8 (2) | H15A—C15—H15B | 108.4 |
C6—N1—Fe1 | 112.71 (16) | O2—C16—H16A | 109.5 |
C1—N1—Fe1 | 139.51 (18) | O2—C16—H16B | 109.5 |
C6—N2—C2 | 107.2 (2) | H16A—C16—H16B | 109.5 |
C6—N2—C3 | 126.1 (2) | O2—C16—H16C | 109.5 |
C2—N2—C3 | 125.9 (2) | H16A—C16—H16C | 109.5 |
C7—N3—C8 | 118.5 (2) | H16B—C16—H16C | 109.5 |
C7—N3—Fe1 | 115.09 (16) | C18—C17—N8 | 106.6 (2) |
C8—N3—Fe1 | 125.94 (16) | C18—C17—H17 | 126.7 |
C10—N4—C19 | 120.0 (2) | N8—C17—H17 | 126.7 |
C10—N4—C9 | 119.9 (2) | N7—C18—C17 | 109.1 (2) |
C19—N4—C9 | 119.5 (2) | N7—C18—H18 | 125.4 |
C21—N5—C20 | 118.0 (2) | C17—C18—H18 | 125.4 |
C21—N5—Fe1 | 115.90 (17) | N4—C19—C20 | 114.3 (2) |
C20—N5—Fe1 | 125.94 (17) | N4—C19—H19A | 108.7 |
C12—N6—C11 | 117.7 (2) | C20—C19—H19A | 108.7 |
C12—N6—Fe1 | 116.09 (18) | N4—C19—H19B | 108.7 |
C11—N6—Fe1 | 126.06 (17) | C20—C19—H19B | 108.7 |
C13—N7—C18 | 106.4 (2) | H19A—C19—H19B | 107.6 |
C13—N7—Fe1 | 112.78 (17) | N5—C20—C19 | 111.8 (2) |
C18—N7—Fe1 | 140.72 (18) | N5—C20—H20A | 109.3 |
C13—N8—C17 | 107.0 (2) | C19—C20—H20A | 109.3 |
C13—N8—C14 | 126.0 (2) | N5—C20—H20B | 109.3 |
C17—N8—C14 | 127.0 (2) | C19—C20—H20B | 109.3 |
C22—N9—C27 | 106.6 (2) | H20A—C20—H20B | 107.9 |
C22—N9—Fe1 | 113.49 (17) | N5—C21—C22 | 113.5 (2) |
C27—N9—Fe1 | 139.85 (19) | N5—C21—H21 | 123.2 |
C22—N10—C26 | 106.7 (2) | C22—C21—H21 | 123.2 |
C22—N10—C23 | 126.4 (2) | N9—C22—N10 | 110.9 (2) |
C26—N10—C23 | 126.2 (2) | N9—C22—C21 | 116.2 (2) |
C2—C1—N1 | 108.6 (2) | N10—C22—C21 | 133.0 (2) |
C2—C1—H1 | 125.7 | N10—C23—C24 | 112.0 (2) |
N1—C1—H1 | 125.7 | N10—C23—H23A | 109.2 |
C1—C2—N2 | 107.2 (2) | C24—C23—H23A | 109.2 |
C1—C2—H2 | 126.4 | N10—C23—H23B | 109.2 |
N2—C2—H2 | 126.4 | C24—C23—H23B | 109.2 |
N2—C3—C4 | 110.3 (2) | H23A—C23—H23B | 107.9 |
N2—C3—H3A | 109.6 | O3—C24—C23 | 109.6 (3) |
C4—C3—H3A | 109.6 | O3—C24—H24 | 125.2 |
N2—C3—H3B | 109.6 | C23—C24—H24 | 125.2 |
C4—C3—H3B | 109.6 | O3—C25—H25A | 109.5 |
H3A—C3—H3B | 108.1 | O3—C25—H25B | 109.5 |
O1—C4—C3 | 107.6 (2) | H25A—C25—H25B | 109.5 |
O1—C4—H4A | 110.2 | O3—C25—H25C | 109.5 |
C3—C4—H4A | 110.2 | H25A—C25—H25C | 109.5 |
O1—C4—H4B | 110.2 | H25B—C25—H25C | 109.5 |
C3—C4—H4B | 110.2 | C27—C26—N10 | 107.4 (2) |
H4A—C4—H4B | 108.5 | C27—C26—H26 | 126.3 |
O1—C5—H5A | 109.5 | N10—C26—H26 | 126.3 |
O1—C5—H5B | 109.5 | C26—C27—N9 | 108.4 (2) |
H5A—C5—H5B | 109.5 | C26—C27—H27 | 125.8 |
O1—C5—H5C | 109.5 | N9—C27—H27 | 125.8 |
H5A—C5—H5C | 109.5 | F4—P1—F1 | 90.33 (10) |
H5B—C5—H5C | 109.5 | F4—P1—F2 | 90.56 (11) |
N1—C6—N2 | 110.2 (2) | F1—P1—F2 | 179.05 (12) |
N1—C6—C7 | 117.0 (2) | F4—P1—F5 | 90.73 (10) |
N2—C6—C7 | 132.7 (2) | F1—P1—F5 | 90.18 (11) |
N3—C7—C6 | 113.5 (2) | F2—P1—F5 | 90.13 (12) |
N3—C7—H7 | 123.3 | F4—P1—F3 | 90.09 (10) |
C6—C7—H7 | 123.3 | F1—P1—F3 | 89.82 (10) |
N3—C8—C9 | 111.9 (2) | F2—P1—F3 | 89.85 (11) |
N3—C8—H8A | 109.2 | F5—P1—F3 | 179.18 (11) |
C9—C8—H8A | 109.2 | F4—P1—F6 | 179.42 (11) |
N3—C8—H8B | 109.2 | F1—P1—F6 | 89.77 (10) |
C9—C8—H8B | 109.2 | F2—P1—F6 | 89.34 (11) |
H8A—C8—H8B | 107.9 | F5—P1—F6 | 89.84 (11) |
N4—C9—C8 | 113.9 (2) | F3—P1—F6 | 89.34 (10) |
N4—C9—H9A | 108.8 | F10—P2—F7 | 90.19 (12) |
C8—C9—H9A | 108.8 | F10—P2—F12 | 179.16 (12) |
N4—C9—H9B | 108.8 | F7—P2—F12 | 90.22 (11) |
C8—C9—H9B | 108.8 | F10—P2—F8 | 90.28 (13) |
H9A—C9—H9B | 107.7 | F7—P2—F8 | 178.96 (12) |
N4—C10—C11 | 113.7 (2) | F12—P2—F8 | 89.31 (11) |
N4—C10—H10A | 108.8 | F10—P2—F9 | 90.48 (13) |
C11—C10—H10A | 108.8 | F7—P2—F9 | 90.41 (11) |
N4—C10—H10B | 108.8 | F12—P2—F9 | 90.25 (11) |
C11—C10—H10B | 108.8 | F8—P2—F9 | 90.52 (13) |
H10A—C10—H10B | 107.7 | F10—P2—F11 | 90.11 (11) |
N6—C11—C10 | 111.5 (2) | F7—P2—F11 | 89.62 (11) |
N6—C11—H11A | 109.3 | F12—P2—F11 | 89.16 (10) |
C10—C11—H11A | 109.3 | F8—P2—F11 | 89.45 (12) |
N6—C11—H11B | 109.3 | F9—P2—F11 | 179.41 (12) |
C10—C11—H11B | 109.3 | ||
C6—N1—C1—C2 | −0.4 (3) | C17—N8—C13—C12 | 177.0 (3) |
Fe1—N1—C1—C2 | 166.7 (2) | C14—N8—C13—C12 | −4.9 (4) |
N1—C1—C2—N2 | 0.4 (3) | N6—C12—C13—N7 | −0.2 (3) |
C6—N2—C2—C1 | −0.2 (3) | N6—C12—C13—N8 | −177.7 (3) |
C3—N2—C2—C1 | −170.2 (2) | C13—N8—C14—C15 | 133.9 (3) |
C6—N2—C3—C4 | −94.1 (3) | C17—N8—C14—C15 | −48.3 (4) |
C2—N2—C3—C4 | 74.0 (3) | C16—O2—C15—C14 | 178.2 (3) |
C5—O1—C4—C3 | −175.7 (2) | N8—C14—C15—O2 | 75.4 (3) |
N2—C3—C4—O1 | 57.1 (3) | C13—N8—C17—C18 | 0.1 (3) |
C1—N1—C6—N2 | 0.3 (3) | C14—N8—C17—C18 | −178.1 (2) |
Fe1—N1—C6—N2 | −170.66 (16) | C13—N7—C18—C17 | −0.8 (3) |
C1—N1—C6—C7 | 177.3 (2) | Fe1—N7—C18—C17 | 176.0 (2) |
Fe1—N1—C6—C7 | 6.4 (3) | N8—C17—C18—N7 | 0.5 (3) |
C2—N2—C6—N1 | −0.1 (3) | C10—N4—C19—C20 | −71.8 (3) |
C3—N2—C6—N1 | 169.9 (2) | C9—N4—C19—C20 | 116.5 (3) |
C2—N2—C6—C7 | −176.5 (3) | C21—N5—C20—C19 | −107.4 (3) |
C3—N2—C6—C7 | −6.5 (4) | Fe1—N5—C20—C19 | 78.0 (3) |
C8—N3—C7—C6 | −179.3 (2) | N4—C19—C20—N5 | −56.6 (3) |
Fe1—N3—C7—C6 | −6.9 (3) | C20—N5—C21—C22 | −179.2 (2) |
N1—C6—C7—N3 | 0.3 (3) | Fe1—N5—C21—C22 | −4.0 (3) |
N2—C6—C7—N3 | 176.5 (3) | C27—N9—C22—N10 | 0.1 (3) |
C7—N3—C8—C9 | −110.9 (3) | Fe1—N9—C22—N10 | −177.21 (16) |
Fe1—N3—C8—C9 | 77.5 (3) | C27—N9—C22—C21 | −178.3 (2) |
C10—N4—C9—C8 | 117.3 (3) | Fe1—N9—C22—C21 | 4.4 (3) |
C19—N4—C9—C8 | −70.9 (3) | C26—N10—C22—N9 | 0.5 (3) |
N3—C8—C9—N4 | −57.6 (3) | C23—N10—C22—N9 | 171.5 (2) |
C19—N4—C10—C11 | 117.7 (3) | C26—N10—C22—C21 | 178.5 (3) |
C9—N4—C10—C11 | −70.6 (3) | C23—N10—C22—C21 | −10.5 (4) |
C12—N6—C11—C10 | −107.0 (3) | N5—C21—C22—N9 | −0.3 (3) |
Fe1—N6—C11—C10 | 78.3 (3) | N5—C21—C22—N10 | −178.2 (3) |
N4—C10—C11—N6 | −58.0 (3) | C22—N10—C23—C24 | −62.9 (4) |
C11—N6—C12—C13 | 179.9 (2) | C26—N10—C23—C24 | 106.3 (3) |
Fe1—N6—C12—C13 | −4.8 (3) | C25—O3—C24—C23 | 161.7 (3) |
C18—N7—C13—N8 | 0.9 (3) | N10—C23—C24—O3 | −56.1 (3) |
Fe1—N7—C13—N8 | −176.94 (16) | C22—N10—C26—C27 | −0.9 (3) |
C18—N7—C13—C12 | −177.1 (2) | C23—N10—C26—C27 | −171.9 (2) |
Fe1—N7—C13—C12 | 5.1 (3) | N10—C26—C27—N9 | 1.0 (3) |
C17—N8—C13—N7 | −0.6 (3) | C22—N9—C27—C26 | −0.7 (3) |
C14—N8—C13—N7 | 177.5 (2) | Fe1—N9—C27—C26 | 175.5 (2) |
Contact | Length | Symmetry operation on atom 2 |
C1···F12 | 3.137 (3) | -x, 1 - y, -z |
C2···F8 | 2.957 (4) | x, 1/2 - y, -1/2 + z |
C12···F11 | 3.044 (3) | -x, -1/2 + y, 1/2 - z |
C13···F11 | 2.934 (3) | -x, -1/2 + y, 1/2 - z |
C21···F1 | 2.902 (3) | 1 - x , -1/2 + y, 1/2 - z |
C22···F1 | 3.022 (3) | 1 - x , -1/2 + y, 1/2 - z |
C25···F10 | 3.074 (4) | x, 3/2 - y, -1/2 + z |
Funding information
We are grateful to H2020 Marie Skłodowska-Curie Actions for financial support (grant No. 734322).
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