research communications
H-imidazole-κN3)(meso-tetra-p-tolylporphyrinato-κ4N)iron(III) perchlorate tetrahydrofuran sesquisolvate
of bis(2-methyl-1aCollege of Materials Science and Optoelectronic Technology, University of Chinese Academy of Sciences, Yianqi Lake, Huairou District, Beijing, 101408, People's Republic of China
*Correspondence e-mail: jfli@ucas.ac.cn
In the title compound, [Fe(C48H36N4)(C4H6N2)2]ClO4·1.5C4H8O, the iron(III) metal is coordinated in a distorted octahedral geometry by four pyrrole N atoms of the porphyrin ligand in the equatorial plane and two N atoms of 2-methylimidazole ligands in the axial sites. The complex has a highly ruffled porphyrin core with mean absolute core-atom displacements Ca, Cb, Cm and Cav of 0.25 (5), 0.17 (12), 0.432 (16) and 0.25 (13) Å, respectively. One of the four phenyl groups of the porphyrin is disordered over two sets of sites with refined occupancy ratio of 0.718 (7):0.282 (7). The mean Fe—Np (Np is a porphyrin N atom) bond length [1.975 (9) Å] indicates the low-spin state of the iron atom. The two 2-methylimidazole ligands are nearly perpendicular and form a dihedral angle of 86.93 (10)°. The dihedral angles between the 2-methylimidazole ligands and the closest Fe—Np vector are 38.04 (9) and 35.00 (7)°. In the crystal, the complex cations interact with the perchlorate anions through N—H⋯O hydrogen bonds, forming chains running parallel to [110].
Keywords: crystal structure; 2-methylimidazole; meso-tetrakis(p-tolyl)porphyrinato; iron(III); highly ruffled porphyrin core; hydrogen bonding.
CCDC reference: 1471779
1. Chemical context
The structural characterization of metalloporphyrin complexes with steric nitrogen-donor ligands has been undertaken intensively in order to understand the control of structures, spin states, and other physical properties. Many structures of ferric L)2]+ (Porph is a porphyrinato ligand and L is an N-bonded neutral ligand) and with the central FeIII atom in an octahedral coordination are known. The first ferric porphyrin with two sterically hindered axial ligands is [Fe(OEP)(2-MeHIm)2]ClO4, which was reported by Geiger and co-workers (Geiger et al., 1984). Subsequently, some other analogues have been reported, [Fe(TPP)(2-MeHIm)2]ClO4 (Scheidt et al., 1987), [Fe(TMP)(1,2-Me2Im)2]ClO4 (Munro et al., 1995), [Fe(OETPP)(2-MeHIm)2]·(0.33SbF6–, 0.67Cl−) (Ogura et al., 2001), [Fe(OMTPP)(2-MeHIm)2]Cl·3CD2Cl2 (Yatsunyk et al., 2003), [Fe(OMTPP)(2-MeHIm)2]Cl·2CDCl3 (Yatsunyk et al., 2003), perp-[Fe(OEP)(2-MeHIm)2]Cl (Hu et al., 2006) (OEP, octaethylporphirin; TPP, tetraphenylporphphyrin; TMP, tetramesitylporphyrin; OETPP, octaethyltetraphenylporphyrin; OMTPP, octamethyltetraphenylporphyrin; 2-MeHIm, 2-methylimidazole; 1,2-Me2Im, 1,2-dimethylimidazole). Herein, we report the structural properties of the iron(III) porphyrin complex [Fe(TTP)(2-MeHIm)2](ClO4)·1.5THF where the metal is likewise octahedrally coordinated.
with general formula [Fe(Porph)(2. Structural commentary
In the title compound (Fig. 1), the counter-ion to the positively charged bis(2-methylimidazole)[meso-tetrakis(p-tolyl)porphyrinato]iron(III) is a negatively charged perchlorate ion. One of the four phenyl groups of the porphyrin is disordered over two sets of sites [0.718 (7):0.282 (7)] and the dihedral angles between the disordered phenyl planes and the 24-atom mean plane are 72.4 (4) and 63.36 (12)°. Additional quantitative information on the structure is given in Fig. 2, which displays the detailed displacements of each porphyrin from the 24-atom mean plane (in units of 0.01 Å). The mean values of the chemically unique bond lengths (in Å) and angles (in degrees), the orientations of the two 2-methylimidazole ligands including the values of the dihedral angles are also shown; the circle represents the position of the methyl group on the axial ligand. As indicated in Fig. 2, the 2-methylimidazole ligand containing the N7 atom makes a dihedral angle of 38.04 (9)°, the other making an angle of 35.00 (7)°, to the closest Fe—Np vector. The relative orientation of the two 2-methylimidazole planes is nearly perpendicular, the dihedral angle being 86.93 (10)°. Fig. 2 also shows that the title complex has a highly ruffled porphyrin core conformation. The mean absolute displacements of Ca, Cb, Cm, and Cav are 0.25 (5), 0.17 (12), 0.432 (16) and 0.25 (13) Å, respectively. The mean Fe—Np (Np is a porphyrin N atom) bond length is 1.975 (9) Å, similar to 1.974 (4) Å in (perp-[Fe(OEP)(2-MeHIm)2]Cl) (Hu et al., 2006) and 1.970 (4) Å in [Fe(TPP)(2-MeHIm)2]ClO4 (Scheidt et al., 1987). These values are slightly shorter than 1.990 Å, which is typically observed for a low-spin iron(III) porphyrin complex (Scheidt & Reed, 1981).
The dihedral angles between the mean planes of the phenyl rings and the 24-atom mean plane are 59.55 (6), 82.53 (7), 72.4 (4) [and/or 63.36 (12)] and 75.17 (5)°, smaller than the same angles of 89.7, 83.3, 87.2 and 87.9° in [Fe(TMP)(1,2-Me2Im)2]ClO4 (Munro et al., 1995). The reason for the difference could be the of the mesityl groups of [Fe(TMP)(1,2-Me2Im)2]ClO4, which hinders the rotation of the benzene groups.
3. Supramolecular features
N—H⋯O hydrogen bonds are observed in the ). As shown in Fig. 3, the perchlorate ion bridges two adjacent porphyrin molecules through hydrogen bonding with imidazole ligands, which can be formulated as N8—H8A⋯O2—ClO2—O3⋯H6A—N6, forming a chain parallel to [110]. The hydrogen-bonding distances, 2.942 (3) (O3⋯N6) and 2.949 (3) Å (O2⋯N8), are consistent with the reported values 2.92 or 3.08 Å (Scheidt et al., 1987; Hu et al., 2006), and fall in the range 2.70–3.30 Å reported for intermolecular N⋯O interactions (Bertolasi et al., 1995). It is noteworthy that one of the tetrahydrofuran molecules, which is disordered about an inversion center, occupies the channels between the [Fe(TTP)(2-MeHIm)2]ClO4 complex molecules (Fig. 4).
of the title compound (Table 14. Synthesis and crystallization
General Procedure: All reactions were carried out using standard Schlenk techniques under argon unless otherwise noted. Tetrahydrofuran (THF) and hexanes were distilled from sodium and benzophenone ketyl. H2(TTP) and [Fe(TTP)Cl] were prepared according to the reported methods (Adler et al., 1970; Fleischer et al., 1971).
4.1. Synthesis of [meso-tetrakis(p-tolyl)porphyrinato]iron(III) perchlorate
[Fe(TTP)Cl] (500 mg, 0.652 mmol) and AgClO4 (136 mg, 0.657 mmol) were dissolved in 50 mL THF. After 12 h reaction, the solution was filtered and then evaporated to dryness under vacuum. The resulting purple solid, [Fe(TTP)ClO4], was harvested that was dried in vacuo (531.54 mg; yield 100%). UV–vis (CH2Cl2): 411.89, 516.5 nm.
4.2. Synthesis of bis(2-methyl-1H-imidazole-κN3)(meso-tetra-p-tolylporphyrinato-κ4N)iron(III) perchlorate tetrahydrofuran sesquisolvate
[Fe(TTP)ClO4] (20 mg, 0.024 mmol) and excess 2-methylimidazole (0.164 g, 2 mmol) were dissolved in 7 mL THF. After 10 min, the solution was transferred into glass tubes which were layered with hexanes as nonsolvent. Dark-purple block-shaped crystals suitable for a single-crystal X-ray diffraction study were collected after 15 d. UV–vis (CH2Cl2): 415.44, 509.68, 571.87, 612.00 nm.
5. Refinement
Crystal data, data collection and structure . The hydrogen atoms of the two imidazole nitrogen atoms of the axial ligands were located in a difference Fourier map and refined freely. All other hydrogen atoms were placed in calculated positions, with C—H = 0.95 or 0.98 Å for aryl or methyl H atoms, respectively, and refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H atoms or Uiso(H) = 1.2Ueq(C, N) otherwise. One THF molecule is disordered over two sets of sites about an inversion center with an occupancy factor of 0.5. During the the O—C, C—C and C⋯C distances within the disordered THF molecule were constrained to be 1.42 (1), 1.50 (1) and 2.40 (1) Å, respectively. One of the four phenyl groups was found to be disordered over two orientations and the site occupancy factors (SOFs) of disordered moieties are refined by means of a `free variable'. The refined final SOFs were 0.718 (7) and 0.282 (7). Two carbon atoms (C39 and C43) of the tetrahydrofuran molecules and one carbon atom (C12) of a methyl group exhibited unusually large displacement parameters and thus were refined using SIMU and ISOR restraints. Seven outliers were omitted in the last cycles of refinement.
details are summarized in Table 2Supporting information
CCDC reference: 1471779
https://doi.org/10.1107/S2056989016010562/rz5191sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016010562/rz5191Isup2.hkl
Data collection: APEX2 (Bruker, 2014); cell
SAINT-Plus (Bruker, 2014); data reduction: SAINT-Plus (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).[Fe(C48H36N4)(C4H6N2)2]ClO4·1.5C4H8O | F(000) = 4600 |
Mr = 1096.48 | Dx = 1.352 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 26.7161 (10) Å | Cell parameters from 9943 reflections |
b = 16.6111 (6) Å | θ = 2.5–27.1° |
c = 24.9673 (8) Å | µ = 0.39 mm−1 |
β = 103.538 (1)° | T = 130 K |
V = 10772.2 (7) Å3 | Block, dark purple |
Z = 8 | 0.52 × 0.23 × 0.20 mm |
Brucker D8 QUEST System diffractometer | 11928 independent reflections |
Radiation source: fine-focus sealed tube | 9751 reflections with I > 2σ(I) |
Detector resolution: 0 pixels mm-1 | Rint = 0.051 |
φ and ω scans | θmax = 27.2°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −34→34 |
Tmin = 0.898, Tmax = 0.925 | k = −21→21 |
120242 measured reflections | l = −32→31 |
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)] = 0.048 | Hydrogen site location: mixed |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0586P)2 + 27.1309P] where P = (Fo2 + 2Fc2)/3 |
11928 reflections | (Δ/σ)max < 0.001 |
772 parameters | Δρmax = 0.77 e Å−3 |
64 restraints | Δρmin = −0.79 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. |
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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.16104 (2) | 0.38552 (2) | 0.14780 (2) | 0.01685 (8) | |
N1 | 0.17087 (7) | 0.42281 (10) | 0.22511 (7) | 0.0204 (3) | |
N2 | 0.20284 (6) | 0.28919 (10) | 0.17281 (7) | 0.0189 (3) | |
N3 | 0.15186 (6) | 0.34956 (10) | 0.07103 (7) | 0.0189 (3) | |
N4 | 0.11862 (6) | 0.48227 (10) | 0.12318 (7) | 0.0193 (3) | |
N5 | 0.22345 (7) | 0.45107 (11) | 0.14473 (7) | 0.0233 (4) | |
N6 | 0.29935 (8) | 0.49768 (13) | 0.14308 (9) | 0.0322 (5) | |
N7 | 0.10050 (6) | 0.31950 (10) | 0.15599 (7) | 0.0195 (3) | |
N8 | 0.03203 (7) | 0.24413 (12) | 0.14613 (8) | 0.0269 (4) | |
C1 | 0.09287 (9) | 0.60715 (15) | 0.24183 (9) | 0.0288 (5) | |
C2 | 0.06470 (10) | 0.59122 (18) | 0.28095 (10) | 0.0385 (6) | |
H2A | 0.0548 | 0.5375 | 0.2864 | 0.046* | |
C3 | 0.05095 (11) | 0.6531 (2) | 0.31211 (11) | 0.0464 (7) | |
H3A | 0.0319 | 0.6409 | 0.3388 | 0.056* | |
C4 | 0.06434 (12) | 0.7319 (2) | 0.30512 (12) | 0.0489 (7) | |
C5 | 0.04932 (16) | 0.7986 (2) | 0.33998 (15) | 0.0738 (12) | |
H5A | 0.0588 | 0.7830 | 0.3789 | 0.111* | |
H5B | 0.0121 | 0.8075 | 0.3288 | 0.111* | |
H5C | 0.0674 | 0.8483 | 0.3347 | 0.111* | |
C6 | 0.09204 (12) | 0.74830 (18) | 0.26575 (13) | 0.0477 (7) | |
H6B | 0.1016 | 0.8022 | 0.2602 | 0.057* | |
C7 | 0.10602 (10) | 0.68681 (15) | 0.23438 (11) | 0.0357 (5) | |
H7A | 0.1248 | 0.6993 | 0.2075 | 0.043* | |
C8 | 0.27637 (10) | 0.30770 (14) | 0.32177 (9) | 0.0308 (5) | |
C9 | 0.26168 (14) | 0.27067 (17) | 0.36579 (11) | 0.0493 (8) | |
H9A | 0.2270 | 0.2543 | 0.3624 | 0.059* | |
C10 | 0.29832 (18) | 0.25788 (18) | 0.41492 (12) | 0.0673 (11) | |
H10A | 0.2884 | 0.2316 | 0.4446 | 0.081* | |
C11 | 0.34866 (17) | 0.28270 (18) | 0.42120 (13) | 0.0652 (11) | |
C12 | 0.38845 (17) | 0.2746 (3) | 0.47557 (16) | 0.0794 (11) | |
H12A | 0.3803 | 0.2276 | 0.4956 | 0.119* | |
H12B | 0.3880 | 0.3232 | 0.4978 | 0.119* | |
H12C | 0.4227 | 0.2679 | 0.4683 | 0.119* | |
C13 | 0.36259 (14) | 0.3182 (2) | 0.37762 (14) | 0.0584 (9) | |
H13A | 0.3973 | 0.3345 | 0.3811 | 0.070* | |
C14 | 0.32659 (11) | 0.33096 (18) | 0.32803 (11) | 0.0433 (6) | |
H14A | 0.3370 | 0.3561 | 0.2982 | 0.052* | |
C15 | 0.19393 (9) | 0.13309 (13) | 0.06029 (9) | 0.0238 (4) | |
C16A | 0.15291 (14) | 0.0846 (2) | 0.03279 (15) | 0.0298 (9) | 0.718 (7) |
H16A | 0.1184 | 0.1006 | 0.0309 | 0.036* | 0.718 (7) |
C17A | 0.16285 (14) | 0.0133 (2) | 0.00834 (16) | 0.0342 (10) | 0.718 (7) |
H17A | 0.1347 | −0.0188 | −0.0104 | 0.041* | 0.718 (7) |
C20A | 0.25309 (17) | 0.0380 (2) | 0.0357 (2) | 0.0334 (9) | 0.718 (7) |
H20A | 0.2874 | 0.0230 | 0.0357 | 0.040* | 0.718 (7) |
C21A | 0.24418 (15) | 0.1092 (2) | 0.06081 (19) | 0.0286 (8) | 0.718 (7) |
H21A | 0.2724 | 0.1420 | 0.0785 | 0.034* | 0.718 (7) |
C16B | 0.1670 (6) | 0.0762 (6) | 0.0652 (5) | 0.068 (4) | 0.282 (7) |
H16B | 0.1376 | 0.0853 | 0.0797 | 0.082* | 0.282 (7) |
C17B | 0.1782 (5) | −0.0104 (7) | 0.0492 (6) | 0.055 (4) | 0.282 (7) |
H17B | 0.1648 | −0.0571 | 0.0629 | 0.066* | 0.282 (7) |
C20B | 0.2370 (5) | 0.0501 (7) | 0.0056 (7) | 0.044 (3) | 0.282 (7) |
H20B | 0.2628 | 0.0473 | −0.0149 | 0.052* | 0.282 (7) |
C21B | 0.2286 (5) | 0.1243 (7) | 0.0294 (7) | 0.045 (3) | 0.282 (7) |
H21B | 0.2482 | 0.1698 | 0.0234 | 0.054* | 0.282 (7) |
C18 | 0.21214 (11) | −0.01254 (15) | 0.01033 (10) | 0.0361 (6) | |
C19 | 0.22246 (13) | −0.09109 (18) | −0.01582 (14) | 0.0525 (8) | |
H19A | 0.1899 | −0.1134 | −0.0372 | 0.079* | |
H19B | 0.2384 | −0.1293 | 0.0130 | 0.079* | |
H19C | 0.2457 | −0.0814 | −0.0402 | 0.079* | |
C22 | 0.09844 (8) | 0.51590 (13) | −0.03016 (9) | 0.0234 (4) | |
C23 | 0.05332 (9) | 0.49667 (16) | −0.06809 (10) | 0.0328 (5) | |
H23A | 0.0317 | 0.4553 | −0.0599 | 0.039* | |
C24 | 0.03932 (10) | 0.53730 (18) | −0.11795 (10) | 0.0380 (6) | |
H24A | 0.0081 | 0.5236 | −0.1433 | 0.046* | |
C25 | 0.06998 (10) | 0.59735 (15) | −0.13145 (10) | 0.0335 (5) | |
C26 | 0.05609 (14) | 0.63851 (18) | −0.18665 (11) | 0.0485 (7) | |
H26A | 0.0187 | 0.6364 | −0.2012 | 0.073* | |
H26B | 0.0732 | 0.6112 | −0.2122 | 0.073* | |
H26C | 0.0673 | 0.6948 | −0.1825 | 0.073* | |
C27 | 0.11408 (11) | 0.61758 (16) | −0.09343 (11) | 0.0401 (6) | |
H27A | 0.1354 | 0.6594 | −0.1016 | 0.048* | |
C28 | 0.12813 (10) | 0.57798 (16) | −0.04309 (10) | 0.0360 (6) | |
H28A | 0.1586 | 0.5937 | −0.0172 | 0.043* | |
C29 | 0.22672 (9) | 0.53233 (14) | 0.16050 (11) | 0.0329 (5) | |
H29A | 0.2000 | 0.5626 | 0.1702 | 0.039* | |
C30 | 0.27349 (10) | 0.56053 (16) | 0.15976 (12) | 0.0400 (6) | |
H30A | 0.2862 | 0.6134 | 0.1689 | 0.048* | |
C31 | 0.26867 (9) | 0.43286 (15) | 0.13458 (10) | 0.0296 (5) | |
C32 | 0.28581 (11) | 0.35627 (17) | 0.11542 (15) | 0.0506 (8) | |
H32A | 0.3169 | 0.3654 | 0.1018 | 0.076* | |
H32B | 0.2585 | 0.3345 | 0.0857 | 0.076* | |
H32C | 0.2935 | 0.3179 | 0.1461 | 0.076* | |
C33 | 0.10220 (8) | 0.27606 (13) | 0.20441 (9) | 0.0250 (4) | |
H33A | 0.1292 | 0.2787 | 0.2368 | 0.030* | |
C34 | 0.05993 (9) | 0.23006 (14) | 0.19819 (9) | 0.0285 (5) | |
H34A | 0.0513 | 0.1950 | 0.2247 | 0.034* | |
C35 | 0.05671 (8) | 0.29830 (13) | 0.12129 (9) | 0.0241 (4) | |
C36 | 0.03539 (9) | 0.32524 (16) | 0.06396 (10) | 0.0326 (5) | |
H36A | −0.0015 | 0.3129 | 0.0533 | 0.049* | |
H36B | 0.0531 | 0.2973 | 0.0392 | 0.049* | |
H36C | 0.0404 | 0.3834 | 0.0614 | 0.049* | |
C101 | 0.14767 (8) | 0.48710 (13) | 0.24429 (9) | 0.0225 (4) | |
C102 | 0.20771 (8) | 0.39485 (13) | 0.26924 (8) | 0.0222 (4) | |
C103 | 0.23263 (8) | 0.27496 (13) | 0.22463 (9) | 0.0229 (4) | |
C104 | 0.20483 (8) | 0.21955 (13) | 0.14336 (9) | 0.0213 (4) | |
C105 | 0.16228 (8) | 0.27430 (13) | 0.05314 (8) | 0.0210 (4) | |
C106 | 0.13440 (8) | 0.39558 (13) | 0.02454 (8) | 0.0209 (4) | |
C107 | 0.10441 (8) | 0.51038 (13) | 0.06986 (8) | 0.0210 (4) | |
C108 | 0.09999 (8) | 0.53740 (13) | 0.15480 (9) | 0.0219 (4) | |
C201 | 0.17010 (9) | 0.49869 (14) | 0.30216 (9) | 0.0276 (5) | |
H20I | 0.1603 | 0.5380 | 0.3254 | 0.033* | |
C202 | 0.20757 (9) | 0.44333 (14) | 0.31710 (9) | 0.0276 (5) | |
H20J | 0.2298 | 0.4373 | 0.3526 | 0.033* | |
C203 | 0.25371 (9) | 0.19535 (14) | 0.22771 (9) | 0.0289 (5) | |
H20C | 0.2763 | 0.1716 | 0.2588 | 0.035* | |
C204 | 0.23555 (9) | 0.16046 (14) | 0.17827 (9) | 0.0286 (5) | |
H20D | 0.2419 | 0.1068 | 0.1684 | 0.034* | |
C205 | 0.15073 (9) | 0.27346 (14) | −0.00599 (9) | 0.0267 (5) | |
H20E | 0.1537 | 0.2285 | −0.0286 | 0.032* | |
C206 | 0.13488 (9) | 0.34813 (14) | −0.02363 (9) | 0.0260 (5) | |
H20F | 0.1258 | 0.3660 | −0.0608 | 0.031* | |
C207 | 0.07487 (8) | 0.58290 (13) | 0.06819 (9) | 0.0250 (4) | |
H20G | 0.0605 | 0.6140 | 0.0363 | 0.030* | |
C208 | 0.07116 (8) | 0.59883 (13) | 0.12012 (9) | 0.0252 (4) | |
H20H | 0.0530 | 0.6423 | 0.1316 | 0.030* | |
C301 | 0.11206 (8) | 0.53968 (13) | 0.21232 (9) | 0.0234 (4) | |
C302 | 0.23792 (8) | 0.32704 (13) | 0.26953 (9) | 0.0236 (4) | |
C303 | 0.18481 (8) | 0.21076 (13) | 0.08682 (9) | 0.0216 (4) | |
C304 | 0.11429 (8) | 0.47294 (13) | 0.02367 (8) | 0.0215 (4) | |
O6 | 0.4567 (5) | 0.4345 (7) | 0.0516 (5) | 0.231 (4) | 0.5 |
C41 | 0.5128 (6) | 0.4673 (7) | −0.0064 (6) | 0.134 (3) | 0.5 |
H41A | 0.5479 | 0.4634 | 0.0175 | 0.160* | 0.5 |
H41B | 0.5138 | 0.4987 | −0.0398 | 0.160* | 0.5 |
C42 | 0.4765 (9) | 0.5015 (9) | 0.0230 (9) | 0.199 (5) | 0.5 |
H42A | 0.4478 | 0.5282 | −0.0032 | 0.239* | 0.5 |
H42B | 0.4940 | 0.5419 | 0.0501 | 0.239* | 0.5 |
C43 | 0.4895 (5) | 0.3869 (6) | −0.0203 (5) | 0.117 (3) | 0.5 |
H43A | 0.4585 | 0.3903 | −0.0510 | 0.140* | 0.5 |
H43B | 0.5144 | 0.3492 | −0.0305 | 0.140* | 0.5 |
C44 | 0.4763 (6) | 0.3621 (7) | 0.0306 (5) | 0.140 (4) | 0.5 |
H44A | 0.5070 | 0.3416 | 0.0573 | 0.168* | 0.5 |
H44B | 0.4497 | 0.3194 | 0.0233 | 0.168* | 0.5 |
Cl1 | 0.08673 (2) | 0.12887 (4) | 0.35815 (3) | 0.03735 (15) | |
O1 | 0.13065 (9) | 0.16939 (16) | 0.34826 (14) | 0.0786 (8) | |
O2 | 0.06869 (9) | 0.16899 (17) | 0.40094 (8) | 0.0667 (7) | |
O3 | 0.09973 (8) | 0.04691 (14) | 0.37399 (9) | 0.0543 (6) | |
O4 | 0.04620 (8) | 0.13067 (13) | 0.30954 (8) | 0.0477 (5) | |
O5 | 0.11480 (11) | −0.04122 (16) | 0.24469 (12) | 0.0730 (7) | |
C37 | 0.13725 (18) | 0.0233 (2) | 0.22114 (18) | 0.0760 (11) | |
H37A | 0.1736 | 0.0110 | 0.2215 | 0.091* | |
H37B | 0.1361 | 0.0735 | 0.2422 | 0.091* | |
C38 | 0.1065 (2) | 0.0324 (3) | 0.16355 (19) | 0.0967 (16) | |
H38A | 0.1219 | 0.0010 | 0.1378 | 0.116* | |
H38B | 0.1044 | 0.0896 | 0.1522 | 0.116* | |
C39 | 0.0546 (2) | 0.0006 (4) | 0.1646 (3) | 0.119 (2) | |
H39A | 0.0444 | −0.0433 | 0.1375 | 0.143* | |
H39B | 0.0284 | 0.0438 | 0.1565 | 0.143* | |
C40 | 0.06130 (17) | −0.0306 (3) | 0.2235 (2) | 0.0971 (16) | |
H40A | 0.0474 | 0.0086 | 0.2461 | 0.117* | |
H40B | 0.0429 | −0.0824 | 0.2235 | 0.117* | |
H6A | 0.3286 (13) | 0.4996 (19) | 0.1394 (13) | 0.046 (9)* | |
H8A | 0.0030 (12) | 0.2249 (18) | 0.1317 (12) | 0.037 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01546 (14) | 0.01825 (15) | 0.01730 (14) | −0.00454 (11) | 0.00480 (10) | −0.00147 (11) |
N1 | 0.0208 (8) | 0.0196 (8) | 0.0209 (8) | −0.0045 (7) | 0.0048 (7) | −0.0015 (7) |
N2 | 0.0190 (8) | 0.0195 (8) | 0.0191 (8) | −0.0034 (7) | 0.0060 (6) | −0.0007 (6) |
N3 | 0.0175 (8) | 0.0203 (8) | 0.0196 (8) | −0.0032 (7) | 0.0061 (6) | −0.0006 (7) |
N4 | 0.0184 (8) | 0.0198 (8) | 0.0203 (8) | −0.0045 (7) | 0.0054 (6) | −0.0019 (7) |
N5 | 0.0202 (9) | 0.0260 (9) | 0.0236 (9) | −0.0063 (7) | 0.0051 (7) | 0.0001 (7) |
N6 | 0.0204 (9) | 0.0323 (11) | 0.0463 (12) | −0.0104 (8) | 0.0130 (9) | −0.0049 (9) |
N7 | 0.0190 (8) | 0.0189 (8) | 0.0221 (8) | −0.0032 (7) | 0.0076 (7) | −0.0031 (7) |
N8 | 0.0200 (9) | 0.0321 (10) | 0.0294 (10) | −0.0113 (8) | 0.0077 (8) | −0.0020 (8) |
C1 | 0.0247 (11) | 0.0336 (12) | 0.0270 (11) | 0.0020 (9) | 0.0038 (9) | −0.0057 (9) |
C2 | 0.0366 (14) | 0.0484 (16) | 0.0324 (13) | −0.0008 (12) | 0.0118 (11) | −0.0074 (11) |
C3 | 0.0407 (15) | 0.067 (2) | 0.0346 (14) | 0.0104 (14) | 0.0146 (12) | −0.0109 (13) |
C4 | 0.0448 (16) | 0.0569 (19) | 0.0408 (15) | 0.0180 (14) | 0.0015 (12) | −0.0170 (14) |
C5 | 0.080 (3) | 0.077 (3) | 0.061 (2) | 0.037 (2) | 0.0098 (19) | −0.0297 (19) |
C6 | 0.0502 (17) | 0.0385 (15) | 0.0510 (17) | 0.0099 (13) | 0.0050 (13) | −0.0124 (13) |
C7 | 0.0342 (13) | 0.0328 (13) | 0.0397 (14) | 0.0032 (10) | 0.0078 (11) | −0.0066 (11) |
C8 | 0.0437 (14) | 0.0204 (11) | 0.0234 (11) | 0.0001 (10) | −0.0023 (10) | −0.0018 (9) |
C9 | 0.078 (2) | 0.0335 (14) | 0.0315 (14) | −0.0141 (14) | 0.0033 (14) | 0.0050 (11) |
C10 | 0.131 (4) | 0.0319 (15) | 0.0289 (14) | −0.0111 (19) | −0.0017 (18) | 0.0085 (12) |
C11 | 0.108 (3) | 0.0256 (14) | 0.0394 (16) | 0.0038 (17) | −0.0291 (18) | −0.0003 (12) |
C12 | 0.0912 (19) | 0.0646 (17) | 0.0625 (16) | 0.0036 (15) | −0.0224 (14) | −0.0008 (14) |
C13 | 0.0556 (19) | 0.0475 (18) | 0.0554 (19) | 0.0009 (15) | −0.0206 (15) | −0.0040 (15) |
C14 | 0.0411 (15) | 0.0450 (16) | 0.0360 (14) | −0.0022 (12) | −0.0065 (11) | 0.0018 (12) |
C15 | 0.0283 (11) | 0.0207 (10) | 0.0236 (10) | −0.0013 (9) | 0.0085 (9) | −0.0019 (8) |
C16A | 0.0308 (18) | 0.0303 (18) | 0.0253 (18) | −0.0022 (14) | 0.0007 (14) | −0.0087 (14) |
C17A | 0.0368 (19) | 0.0274 (18) | 0.036 (2) | −0.0046 (14) | 0.0042 (15) | −0.0106 (15) |
C20A | 0.034 (2) | 0.032 (2) | 0.037 (2) | 0.0063 (16) | 0.0129 (18) | −0.0034 (18) |
C21A | 0.0280 (18) | 0.0273 (18) | 0.032 (2) | 0.0005 (14) | 0.0092 (16) | −0.0044 (15) |
C16B | 0.054 (6) | 0.081 (7) | 0.080 (8) | −0.006 (6) | 0.037 (6) | −0.049 (6) |
C17B | 0.069 (8) | 0.034 (6) | 0.067 (9) | −0.011 (5) | 0.023 (7) | −0.007 (5) |
C20B | 0.042 (6) | 0.036 (6) | 0.062 (9) | 0.008 (5) | 0.029 (6) | −0.004 (6) |
C21B | 0.037 (6) | 0.030 (5) | 0.075 (10) | −0.010 (4) | 0.029 (6) | −0.012 (6) |
C18 | 0.0474 (15) | 0.0286 (12) | 0.0319 (12) | 0.0049 (11) | 0.0085 (11) | −0.0069 (10) |
C19 | 0.064 (2) | 0.0363 (15) | 0.0539 (18) | 0.0110 (14) | 0.0075 (15) | −0.0170 (13) |
C22 | 0.0263 (11) | 0.0247 (11) | 0.0211 (10) | −0.0004 (8) | 0.0092 (8) | 0.0006 (8) |
C23 | 0.0279 (12) | 0.0428 (14) | 0.0270 (11) | −0.0052 (10) | 0.0052 (9) | 0.0075 (10) |
C24 | 0.0321 (13) | 0.0541 (16) | 0.0262 (12) | 0.0029 (12) | 0.0035 (10) | 0.0065 (11) |
C25 | 0.0461 (14) | 0.0333 (13) | 0.0247 (11) | 0.0128 (11) | 0.0161 (10) | 0.0063 (10) |
C26 | 0.076 (2) | 0.0449 (16) | 0.0288 (13) | 0.0184 (15) | 0.0200 (13) | 0.0121 (12) |
C27 | 0.0515 (16) | 0.0359 (14) | 0.0365 (14) | −0.0089 (12) | 0.0180 (12) | 0.0084 (11) |
C28 | 0.0371 (13) | 0.0372 (14) | 0.0325 (12) | −0.0113 (11) | 0.0057 (10) | 0.0048 (10) |
C29 | 0.0291 (12) | 0.0267 (12) | 0.0463 (14) | −0.0061 (9) | 0.0161 (11) | −0.0071 (10) |
C30 | 0.0337 (13) | 0.0298 (13) | 0.0603 (17) | −0.0117 (11) | 0.0183 (12) | −0.0106 (12) |
C31 | 0.0233 (11) | 0.0312 (12) | 0.0358 (12) | −0.0058 (9) | 0.0102 (9) | −0.0029 (10) |
C32 | 0.0365 (15) | 0.0377 (15) | 0.088 (2) | −0.0111 (12) | 0.0349 (15) | −0.0188 (15) |
C33 | 0.0256 (11) | 0.0275 (11) | 0.0242 (10) | −0.0042 (9) | 0.0101 (8) | −0.0007 (9) |
C34 | 0.0298 (11) | 0.0301 (12) | 0.0286 (11) | −0.0060 (9) | 0.0131 (9) | 0.0008 (9) |
C35 | 0.0188 (10) | 0.0263 (11) | 0.0287 (11) | −0.0037 (8) | 0.0083 (8) | −0.0041 (9) |
C36 | 0.0232 (11) | 0.0428 (14) | 0.0305 (12) | −0.0082 (10) | 0.0040 (9) | 0.0026 (10) |
C101 | 0.0227 (10) | 0.0227 (10) | 0.0228 (10) | −0.0056 (8) | 0.0071 (8) | −0.0036 (8) |
C102 | 0.0256 (10) | 0.0227 (10) | 0.0179 (9) | −0.0063 (8) | 0.0041 (8) | −0.0016 (8) |
C103 | 0.0223 (10) | 0.0237 (10) | 0.0218 (10) | −0.0024 (8) | 0.0035 (8) | 0.0001 (8) |
C104 | 0.0200 (9) | 0.0212 (10) | 0.0235 (10) | −0.0021 (8) | 0.0068 (8) | −0.0006 (8) |
C105 | 0.0197 (9) | 0.0230 (10) | 0.0218 (10) | −0.0025 (8) | 0.0079 (8) | −0.0023 (8) |
C106 | 0.0190 (10) | 0.0266 (11) | 0.0182 (9) | −0.0060 (8) | 0.0062 (8) | 0.0001 (8) |
C107 | 0.0185 (9) | 0.0224 (10) | 0.0220 (10) | −0.0049 (8) | 0.0042 (8) | 0.0009 (8) |
C108 | 0.0191 (9) | 0.0233 (10) | 0.0238 (10) | −0.0032 (8) | 0.0060 (8) | −0.0030 (8) |
C201 | 0.0332 (12) | 0.0266 (11) | 0.0230 (11) | −0.0046 (9) | 0.0067 (9) | −0.0072 (9) |
C202 | 0.0342 (12) | 0.0259 (11) | 0.0210 (10) | −0.0068 (9) | 0.0031 (9) | −0.0036 (9) |
C203 | 0.0324 (12) | 0.0261 (11) | 0.0254 (11) | 0.0019 (9) | 0.0009 (9) | 0.0012 (9) |
C204 | 0.0331 (12) | 0.0216 (11) | 0.0301 (11) | 0.0032 (9) | 0.0056 (9) | −0.0011 (9) |
C205 | 0.0315 (11) | 0.0292 (11) | 0.0208 (10) | −0.0012 (9) | 0.0090 (9) | −0.0041 (9) |
C206 | 0.0298 (11) | 0.0305 (12) | 0.0195 (10) | −0.0016 (9) | 0.0094 (9) | −0.0004 (9) |
C207 | 0.0232 (10) | 0.0245 (11) | 0.0266 (11) | −0.0020 (8) | 0.0044 (8) | 0.0024 (9) |
C208 | 0.0218 (10) | 0.0240 (11) | 0.0296 (11) | 0.0000 (8) | 0.0059 (9) | −0.0019 (9) |
C301 | 0.0202 (10) | 0.0259 (11) | 0.0253 (10) | −0.0030 (8) | 0.0077 (8) | −0.0039 (8) |
C302 | 0.0257 (11) | 0.0227 (10) | 0.0210 (10) | −0.0064 (8) | 0.0024 (8) | 0.0007 (8) |
C303 | 0.0206 (10) | 0.0211 (10) | 0.0251 (10) | −0.0018 (8) | 0.0093 (8) | −0.0032 (8) |
C304 | 0.0191 (9) | 0.0253 (10) | 0.0202 (10) | −0.0052 (8) | 0.0047 (8) | 0.0015 (8) |
O6 | 0.254 (9) | 0.178 (8) | 0.254 (9) | −0.026 (8) | 0.043 (8) | −0.002 (7) |
C41 | 0.152 (7) | 0.122 (7) | 0.163 (8) | −0.039 (6) | 0.111 (6) | −0.001 (6) |
C42 | 0.229 (9) | 0.160 (9) | 0.217 (10) | −0.040 (8) | 0.073 (8) | 0.014 (8) |
C43 | 0.118 (6) | 0.101 (5) | 0.148 (6) | −0.010 (5) | 0.065 (5) | −0.035 (5) |
C44 | 0.144 (7) | 0.107 (7) | 0.185 (8) | −0.001 (6) | 0.067 (6) | −0.051 (6) |
Cl1 | 0.0258 (3) | 0.0514 (4) | 0.0370 (3) | 0.0186 (3) | 0.0116 (2) | 0.0069 (3) |
O1 | 0.0361 (12) | 0.0641 (16) | 0.144 (3) | 0.0085 (11) | 0.0388 (15) | 0.0125 (16) |
O2 | 0.0532 (13) | 0.109 (2) | 0.0331 (10) | 0.0416 (14) | 0.0008 (9) | −0.0140 (12) |
O3 | 0.0407 (11) | 0.0632 (14) | 0.0648 (14) | 0.0280 (10) | 0.0242 (10) | 0.0295 (11) |
O4 | 0.0520 (12) | 0.0594 (13) | 0.0298 (9) | 0.0218 (10) | 0.0059 (8) | 0.0043 (9) |
O5 | 0.0675 (17) | 0.0644 (16) | 0.0877 (19) | 0.0018 (13) | 0.0192 (14) | −0.0059 (14) |
C37 | 0.094 (3) | 0.057 (2) | 0.077 (3) | −0.006 (2) | 0.022 (2) | −0.005 (2) |
C38 | 0.126 (5) | 0.075 (3) | 0.080 (3) | 0.030 (3) | 0.007 (3) | −0.010 (2) |
C39 | 0.108 (4) | 0.111 (4) | 0.115 (4) | 0.037 (3) | −0.021 (3) | −0.023 (3) |
C40 | 0.061 (3) | 0.090 (3) | 0.138 (5) | 0.001 (2) | 0.020 (3) | −0.041 (3) |
Fe1—N3 | 1.9673 (17) | C23—H23A | 0.9500 |
Fe1—N2 | 1.9675 (17) | C24—C25 | 1.382 (4) |
Fe1—N4 | 1.9797 (18) | C24—H24A | 0.9500 |
Fe1—N1 | 1.9853 (17) | C25—C27 | 1.371 (4) |
Fe1—N7 | 2.0039 (17) | C25—C26 | 1.505 (3) |
Fe1—N5 | 2.0078 (17) | C26—H26A | 0.9800 |
N1—C102 | 1.375 (3) | C26—H26B | 0.9800 |
N1—C101 | 1.376 (3) | C26—H26C | 0.9800 |
N2—C103 | 1.372 (3) | C27—C28 | 1.390 (4) |
N2—C104 | 1.378 (3) | C27—H27A | 0.9500 |
N3—C106 | 1.377 (3) | C28—H28A | 0.9500 |
N3—C105 | 1.378 (3) | C29—C30 | 1.339 (3) |
N4—C108 | 1.376 (3) | C29—H29A | 0.9500 |
N4—C107 | 1.377 (3) | C30—H30A | 0.9500 |
N5—C31 | 1.326 (3) | C31—C32 | 1.470 (4) |
N5—C29 | 1.403 (3) | C32—H32A | 0.9800 |
N6—C31 | 1.340 (3) | C32—H32B | 0.9800 |
N6—C30 | 1.370 (3) | C32—H32C | 0.9800 |
N6—H6A | 0.81 (3) | C33—C34 | 1.342 (3) |
N7—C35 | 1.330 (3) | C33—H33A | 0.9500 |
N7—C33 | 1.399 (3) | C34—H34A | 0.9500 |
N8—C35 | 1.349 (3) | C35—C36 | 1.481 (3) |
N8—C34 | 1.359 (3) | C36—H36A | 0.9800 |
N8—H8A | 0.84 (3) | C36—H36B | 0.9800 |
C1—C2 | 1.391 (3) | C36—H36C | 0.9800 |
C1—C7 | 1.393 (4) | C101—C301 | 1.396 (3) |
C1—C301 | 1.496 (3) | C101—C201 | 1.442 (3) |
C2—C3 | 1.390 (4) | C102—C302 | 1.385 (3) |
C2—H2A | 0.9500 | C102—C202 | 1.442 (3) |
C3—C4 | 1.379 (5) | C103—C302 | 1.397 (3) |
C3—H3A | 0.9500 | C103—C203 | 1.432 (3) |
C4—C6 | 1.389 (5) | C104—C303 | 1.395 (3) |
C4—C5 | 1.519 (4) | C104—C204 | 1.436 (3) |
C5—H5A | 0.9800 | C105—C303 | 1.395 (3) |
C5—H5B | 0.9800 | C105—C205 | 1.436 (3) |
C5—H5C | 0.9800 | C106—C304 | 1.391 (3) |
C6—C7 | 1.390 (4) | C106—C206 | 1.440 (3) |
C6—H6B | 0.9500 | C107—C304 | 1.389 (3) |
C7—H7A | 0.9500 | C107—C207 | 1.435 (3) |
C8—C14 | 1.370 (4) | C108—C301 | 1.397 (3) |
C8—C9 | 1.394 (4) | C108—C208 | 1.439 (3) |
C8—C302 | 1.494 (3) | C201—C202 | 1.346 (3) |
C9—C10 | 1.395 (4) | C201—H20I | 0.9500 |
C9—H9A | 0.9500 | C202—H20J | 0.9500 |
C10—C11 | 1.380 (6) | C203—C204 | 1.347 (3) |
C10—H10A | 0.9500 | C203—H20C | 0.9500 |
C11—C13 | 1.364 (5) | C204—H20D | 0.9500 |
C11—C12 | 1.522 (4) | C205—C206 | 1.351 (3) |
C12—H12A | 0.9800 | C205—H20E | 0.9500 |
C12—H12B | 0.9800 | C206—H20F | 0.9500 |
C12—H12C | 0.9800 | C207—C208 | 1.349 (3) |
C13—C14 | 1.395 (4) | C207—H20G | 0.9500 |
C13—H13A | 0.9500 | C208—H20H | 0.9500 |
C14—H14A | 0.9500 | O6—C44 | 1.456 (9) |
C15—C16B | 1.212 (11) | O6—C42 | 1.486 (9) |
C15—C21B | 1.345 (11) | C41—C42 | 1.459 (9) |
C15—C21A | 1.397 (4) | C41—C43 | 1.480 (9) |
C15—C16A | 1.403 (4) | C41—H41A | 0.9900 |
C15—C303 | 1.496 (3) | C41—H41B | 0.9900 |
C16A—C17A | 1.387 (5) | C42—H42A | 0.9900 |
C16A—H16A | 0.9500 | C42—H42B | 0.9900 |
C17A—C18 | 1.375 (5) | C43—C44 | 1.456 (9) |
C17A—H17A | 0.9500 | C43—H43A | 0.9900 |
C20A—C21A | 1.385 (5) | C43—H43B | 0.9900 |
C20A—C18 | 1.406 (5) | C44—H44A | 0.9900 |
C20A—H20A | 0.9500 | C44—H44B | 0.9900 |
C21A—H21A | 0.9500 | Cl1—O1 | 1.423 (2) |
C16B—C17B | 1.540 (15) | Cl1—O4 | 1.425 (2) |
C16B—H16B | 0.9500 | Cl1—O2 | 1.435 (2) |
C17B—C18 | 1.476 (13) | Cl1—O3 | 1.438 (2) |
C17B—H17B | 0.9500 | O5—C40 | 1.414 (5) |
C20B—C18 | 1.255 (12) | O5—C37 | 1.421 (5) |
C20B—C21B | 1.409 (15) | C37—C38 | 1.487 (6) |
C20B—H20B | 0.9500 | C37—H37A | 0.9900 |
C21B—H21B | 0.9500 | C37—H37B | 0.9900 |
C18—C19 | 1.513 (3) | C38—C39 | 1.488 (8) |
C19—H19A | 0.9800 | C38—H38A | 0.9900 |
C19—H19B | 0.9800 | C38—H38B | 0.9900 |
C19—H19C | 0.9800 | C39—C40 | 1.530 (8) |
C22—C28 | 1.384 (3) | C39—H39A | 0.9900 |
C22—C23 | 1.385 (3) | C39—H39B | 0.9900 |
C22—C304 | 1.493 (3) | C40—H40A | 0.9900 |
C23—C24 | 1.388 (3) | C40—H40B | 0.9900 |
N3—Fe1—N2 | 89.67 (7) | C22—C28—C27 | 121.0 (2) |
N3—Fe1—N4 | 90.70 (7) | C22—C28—H28A | 119.5 |
N2—Fe1—N4 | 179.46 (7) | C27—C28—H28A | 119.5 |
N3—Fe1—N1 | 179.33 (7) | C30—C29—N5 | 109.3 (2) |
N2—Fe1—N1 | 90.52 (7) | C30—C29—H29A | 125.4 |
N4—Fe1—N1 | 89.11 (7) | N5—C29—H29A | 125.4 |
N3—Fe1—N7 | 90.78 (7) | C29—C30—N6 | 106.0 (2) |
N2—Fe1—N7 | 86.23 (7) | C29—C30—H30A | 127.0 |
N4—Fe1—N7 | 93.38 (7) | N6—C30—H30A | 127.0 |
N1—Fe1—N7 | 89.87 (7) | N5—C31—N6 | 109.7 (2) |
N3—Fe1—N5 | 92.46 (7) | N5—C31—C32 | 128.8 (2) |
N2—Fe1—N5 | 92.20 (7) | N6—C31—C32 | 121.4 (2) |
N4—Fe1—N5 | 88.17 (7) | C31—C32—H32A | 109.5 |
N1—Fe1—N5 | 86.90 (7) | C31—C32—H32B | 109.5 |
N7—Fe1—N5 | 176.39 (7) | H32A—C32—H32B | 109.5 |
C102—N1—C101 | 106.24 (17) | C31—C32—H32C | 109.5 |
C102—N1—Fe1 | 125.50 (14) | H32A—C32—H32C | 109.5 |
C101—N1—Fe1 | 127.79 (14) | H32B—C32—H32C | 109.5 |
C103—N2—C104 | 105.79 (17) | C34—C33—N7 | 109.7 (2) |
C103—N2—Fe1 | 126.90 (14) | C34—C33—H33A | 125.1 |
C104—N2—Fe1 | 127.10 (14) | N7—C33—H33A | 125.1 |
C106—N3—C105 | 106.54 (17) | C33—C34—N8 | 105.72 (19) |
C106—N3—Fe1 | 126.38 (14) | C33—C34—H34A | 127.1 |
C105—N3—Fe1 | 127.08 (14) | N8—C34—H34A | 127.1 |
C108—N4—C107 | 105.90 (17) | N7—C35—N8 | 109.10 (19) |
C108—N4—Fe1 | 128.30 (14) | N7—C35—C36 | 129.1 (2) |
C107—N4—Fe1 | 125.70 (14) | N8—C35—C36 | 121.81 (19) |
C31—N5—C29 | 105.87 (18) | C35—C36—H36A | 109.5 |
C31—N5—Fe1 | 133.27 (16) | C35—C36—H36B | 109.5 |
C29—N5—Fe1 | 120.58 (15) | H36A—C36—H36B | 109.5 |
C31—N6—C30 | 109.1 (2) | C35—C36—H36C | 109.5 |
C31—N6—H6A | 126 (2) | H36A—C36—H36C | 109.5 |
C30—N6—H6A | 125 (2) | H36B—C36—H36C | 109.5 |
C35—N7—C33 | 105.78 (17) | N1—C101—C301 | 126.07 (19) |
C35—N7—Fe1 | 133.34 (15) | N1—C101—C201 | 109.70 (19) |
C33—N7—Fe1 | 120.44 (14) | C301—C101—C201 | 123.9 (2) |
C35—N8—C34 | 109.68 (19) | N1—C102—C302 | 125.87 (19) |
C35—N8—H8A | 124 (2) | N1—C102—C202 | 109.59 (19) |
C34—N8—H8A | 126 (2) | C302—C102—C202 | 124.4 (2) |
C2—C1—C7 | 118.0 (2) | N2—C103—C302 | 125.3 (2) |
C2—C1—C301 | 120.5 (2) | N2—C103—C203 | 110.10 (18) |
C7—C1—C301 | 121.3 (2) | C302—C103—C203 | 124.3 (2) |
C3—C2—C1 | 120.6 (3) | N2—C104—C303 | 125.02 (19) |
C3—C2—H2A | 119.7 | N2—C104—C204 | 109.75 (18) |
C1—C2—H2A | 119.7 | C303—C104—C204 | 124.9 (2) |
C4—C3—C2 | 121.4 (3) | N3—C105—C303 | 125.62 (18) |
C4—C3—H3A | 119.3 | N3—C105—C205 | 109.34 (18) |
C2—C3—H3A | 119.3 | C303—C105—C205 | 124.82 (19) |
C3—C4—C6 | 118.2 (3) | N3—C106—C304 | 125.42 (19) |
C3—C4—C5 | 120.5 (3) | N3—C106—C206 | 109.43 (19) |
C6—C4—C5 | 121.3 (3) | C304—C106—C206 | 124.84 (19) |
C4—C5—H5A | 109.5 | N4—C107—C304 | 125.99 (19) |
C4—C5—H5B | 109.5 | N4—C107—C207 | 109.75 (18) |
H5A—C5—H5B | 109.5 | C304—C107—C207 | 124.17 (19) |
C4—C5—H5C | 109.5 | N4—C108—C301 | 125.5 (2) |
H5A—C5—H5C | 109.5 | N4—C108—C208 | 109.94 (18) |
H5B—C5—H5C | 109.5 | C301—C108—C208 | 124.2 (2) |
C4—C6—C7 | 120.9 (3) | C202—C201—C101 | 107.1 (2) |
C4—C6—H6B | 119.6 | C202—C201—H20I | 126.4 |
C7—C6—H6B | 119.6 | C101—C201—H20I | 126.4 |
C6—C7—C1 | 120.9 (3) | C201—C202—C102 | 107.3 (2) |
C6—C7—H7A | 119.6 | C201—C202—H20J | 126.3 |
C1—C7—H7A | 119.6 | C102—C202—H20J | 126.3 |
C14—C8—C9 | 118.9 (2) | C204—C203—C103 | 107.2 (2) |
C14—C8—C302 | 119.6 (2) | C204—C203—H20C | 126.4 |
C9—C8—C302 | 121.4 (2) | C103—C203—H20C | 126.4 |
C8—C9—C10 | 119.4 (3) | C203—C204—C104 | 107.1 (2) |
C8—C9—H9A | 120.3 | C203—C204—H20D | 126.4 |
C10—C9—H9A | 120.3 | C104—C204—H20D | 126.4 |
C11—C10—C9 | 121.3 (3) | C206—C205—C105 | 107.56 (19) |
C11—C10—H10A | 119.4 | C206—C205—H20E | 126.2 |
C9—C10—H10A | 119.4 | C105—C205—H20E | 126.2 |
C13—C11—C10 | 118.6 (3) | C205—C206—C106 | 107.07 (19) |
C13—C11—C12 | 119.1 (4) | C205—C206—H20F | 126.5 |
C10—C11—C12 | 122.3 (4) | C106—C206—H20F | 126.5 |
C11—C12—H12A | 109.5 | C208—C207—C107 | 107.46 (19) |
C11—C12—H12B | 109.5 | C208—C207—H20G | 126.3 |
H12A—C12—H12B | 109.5 | C107—C207—H20G | 126.3 |
C11—C12—H12C | 109.5 | C207—C208—C108 | 106.85 (19) |
H12A—C12—H12C | 109.5 | C207—C208—H20H | 126.6 |
H12B—C12—H12C | 109.5 | C108—C208—H20H | 126.6 |
C11—C13—C14 | 120.9 (3) | C101—C301—C108 | 122.2 (2) |
C11—C13—H13A | 119.5 | C101—C301—C1 | 116.95 (19) |
C14—C13—H13A | 119.5 | C108—C301—C1 | 120.2 (2) |
C8—C14—C13 | 120.8 (3) | C102—C302—C103 | 123.4 (2) |
C8—C14—H14A | 119.6 | C102—C302—C8 | 117.39 (19) |
C13—C14—H14A | 119.6 | C103—C302—C8 | 119.2 (2) |
C16B—C15—C21B | 118.6 (6) | C105—C303—C104 | 122.67 (19) |
C21A—C15—C16A | 118.7 (3) | C105—C303—C15 | 118.52 (18) |
C16B—C15—C303 | 117.7 (5) | C104—C303—C15 | 118.34 (19) |
C21B—C15—C303 | 123.6 (5) | C107—C304—C106 | 123.26 (19) |
C21A—C15—C303 | 119.8 (2) | C107—C304—C22 | 117.68 (19) |
C16A—C15—C303 | 121.5 (2) | C106—C304—C22 | 118.87 (18) |
C17A—C16A—C15 | 119.9 (3) | C44—O6—C42 | 104.2 (8) |
C17A—C16A—H16A | 120.1 | C42—C41—C43 | 100.2 (9) |
C15—C16A—H16A | 120.1 | C42—C41—H41A | 111.7 |
C18—C17A—C16A | 122.1 (3) | C43—C41—H41A | 111.7 |
C18—C17A—H17A | 119.0 | C42—C41—H41B | 111.7 |
C16A—C17A—H17A | 119.0 | C43—C41—H41B | 111.7 |
C21A—C20A—C18 | 121.0 (3) | H41A—C41—H41B | 109.5 |
C21A—C20A—H20A | 119.5 | C41—C42—O6 | 107.7 (9) |
C18—C20A—H20A | 119.5 | C41—C42—H42A | 110.2 |
C20A—C21A—C15 | 120.3 (3) | O6—C42—H42A | 110.2 |
C20A—C21A—H21A | 119.8 | C41—C42—H42B | 110.2 |
C15—C21A—H21A | 119.8 | O6—C42—H42B | 110.2 |
C15—C16B—C17B | 123.0 (9) | H42A—C42—H42B | 108.5 |
C15—C16B—H16B | 118.5 | C44—C43—C41 | 102.9 (8) |
C17B—C16B—H16B | 118.5 | C44—C43—H43A | 111.2 |
C18—C17B—C16B | 112.4 (8) | C41—C43—H43A | 111.2 |
C18—C17B—H17B | 123.8 | C44—C43—H43B | 111.2 |
C16B—C17B—H17B | 123.8 | C41—C43—H43B | 111.2 |
C18—C20B—C21B | 123.1 (9) | H43A—C43—H43B | 109.1 |
C18—C20B—H20B | 118.5 | C43—C44—O6 | 105.2 (8) |
C21B—C20B—H20B | 118.5 | C43—C44—H44A | 110.7 |
C15—C21B—C20B | 122.4 (9) | O6—C44—H44A | 110.7 |
C15—C21B—H21B | 118.8 | C43—C44—H44B | 110.7 |
C20B—C21B—H21B | 118.8 | O6—C44—H44B | 110.7 |
C17A—C18—C20A | 117.9 (3) | H44A—C44—H44B | 108.8 |
C20B—C18—C17B | 117.5 (7) | O1—Cl1—O4 | 109.59 (17) |
C20B—C18—C19 | 121.4 (5) | O1—Cl1—O2 | 110.10 (18) |
C17A—C18—C19 | 121.5 (3) | O4—Cl1—O2 | 107.68 (12) |
C20A—C18—C19 | 120.5 (3) | O1—Cl1—O3 | 109.86 (13) |
C17B—C18—C19 | 120.5 (5) | O4—Cl1—O3 | 109.91 (14) |
C18—C19—H19A | 109.5 | O2—Cl1—O3 | 109.67 (15) |
C18—C19—H19B | 109.5 | C40—O5—C37 | 103.8 (4) |
H19A—C19—H19B | 109.5 | O5—C37—C38 | 106.6 (4) |
C18—C19—H19C | 109.5 | O5—C37—H37A | 110.4 |
H19A—C19—H19C | 109.5 | C38—C37—H37A | 110.4 |
H19B—C19—H19C | 109.5 | O5—C37—H37B | 110.4 |
C28—C22—C23 | 117.8 (2) | C38—C37—H37B | 110.4 |
C28—C22—C304 | 120.6 (2) | H37A—C37—H37B | 108.6 |
C23—C22—C304 | 121.57 (19) | C37—C38—C39 | 104.7 (4) |
C22—C23—C24 | 120.6 (2) | C37—C38—H38A | 110.8 |
C22—C23—H23A | 119.7 | C39—C38—H38A | 110.8 |
C24—C23—H23A | 119.7 | C37—C38—H38B | 110.8 |
C25—C24—C23 | 121.3 (2) | C39—C38—H38B | 110.8 |
C25—C24—H24A | 119.4 | H38A—C38—H38B | 108.9 |
C23—C24—H24A | 119.4 | C38—C39—C40 | 103.8 (4) |
C27—C25—C24 | 118.1 (2) | C38—C39—H39A | 111.0 |
C27—C25—C26 | 120.7 (3) | C40—C39—H39A | 111.0 |
C24—C25—C26 | 121.2 (3) | C38—C39—H39B | 111.0 |
C25—C26—H26A | 109.5 | C40—C39—H39B | 111.0 |
C25—C26—H26B | 109.5 | H39A—C39—H39B | 109.0 |
H26A—C26—H26B | 109.5 | O5—C40—C39 | 106.4 (4) |
C25—C26—H26C | 109.5 | O5—C40—H40A | 110.5 |
H26A—C26—H26C | 109.5 | C39—C40—H40A | 110.5 |
H26B—C26—H26C | 109.5 | O5—C40—H40B | 110.5 |
C25—C27—C28 | 121.1 (2) | C39—C40—H40B | 110.5 |
C25—C27—H27A | 119.5 | H40A—C40—H40B | 108.6 |
C28—C27—H27A | 119.5 | ||
C7—C1—C2—C3 | −1.0 (4) | C105—N3—C106—C206 | −1.1 (2) |
C301—C1—C2—C3 | 173.9 (2) | Fe1—N3—C106—C206 | 177.96 (13) |
C1—C2—C3—C4 | 0.5 (4) | C108—N4—C107—C304 | −178.7 (2) |
C2—C3—C4—C6 | 0.2 (4) | Fe1—N4—C107—C304 | 4.7 (3) |
C2—C3—C4—C5 | −179.5 (3) | C108—N4—C107—C207 | −2.0 (2) |
C3—C4—C6—C7 | −0.2 (4) | Fe1—N4—C107—C207 | −178.55 (13) |
C5—C4—C6—C7 | 179.4 (3) | C107—N4—C108—C301 | −169.7 (2) |
C4—C6—C7—C1 | −0.4 (4) | Fe1—N4—C108—C301 | 6.8 (3) |
C2—C1—C7—C6 | 1.0 (4) | C107—N4—C108—C208 | 3.2 (2) |
C301—C1—C7—C6 | −173.9 (2) | Fe1—N4—C108—C208 | 179.60 (14) |
C14—C8—C9—C10 | −0.3 (4) | N1—C101—C201—C202 | 1.9 (3) |
C302—C8—C9—C10 | −176.4 (3) | C301—C101—C201—C202 | −171.4 (2) |
C8—C9—C10—C11 | 1.4 (5) | C101—C201—C202—C102 | −2.0 (3) |
C9—C10—C11—C13 | −1.9 (5) | N1—C102—C202—C201 | 1.5 (3) |
C9—C10—C11—C12 | 175.7 (3) | C302—C102—C202—C201 | −174.1 (2) |
C10—C11—C13—C14 | 1.4 (5) | N2—C103—C203—C204 | −1.7 (3) |
C12—C11—C13—C14 | −176.3 (3) | C302—C103—C203—C204 | 172.7 (2) |
C9—C8—C14—C13 | −0.2 (4) | C103—C203—C204—C104 | 2.5 (3) |
C302—C8—C14—C13 | 175.9 (3) | N2—C104—C204—C203 | −2.5 (3) |
C11—C13—C14—C8 | −0.3 (5) | C303—C104—C204—C203 | 171.0 (2) |
C21A—C15—C16A—C17A | 2.0 (5) | N3—C105—C205—C206 | 1.7 (2) |
C303—C15—C16A—C17A | 179.5 (3) | C303—C105—C205—C206 | −173.1 (2) |
C15—C16A—C17A—C18 | 0.5 (6) | C105—C205—C206—C106 | −2.3 (2) |
C18—C20A—C21A—C15 | −1.4 (6) | N3—C106—C206—C205 | 2.2 (2) |
C16A—C15—C21A—C20A | −1.5 (5) | C304—C106—C206—C205 | −171.6 (2) |
C303—C15—C21A—C20A | −179.1 (3) | N4—C107—C207—C208 | 0.0 (2) |
C21B—C15—C16B—C17B | 14.2 (17) | C304—C107—C207—C208 | 176.8 (2) |
C303—C15—C16B—C17B | −168.8 (9) | C107—C207—C208—C108 | 1.9 (2) |
C15—C16B—C17B—C18 | −20.5 (17) | N4—C108—C208—C207 | −3.2 (2) |
C16B—C15—C21B—C20B | −4.2 (18) | C301—C108—C208—C207 | 169.7 (2) |
C303—C15—C21B—C20B | 178.9 (10) | N1—C101—C301—C108 | −7.2 (3) |
C18—C20B—C21B—C15 | 2 (2) | C201—C101—C301—C108 | 165.0 (2) |
C21B—C20B—C18—C17B | −9.2 (18) | N1—C101—C301—C1 | −178.28 (19) |
C21B—C20B—C18—C19 | −179.9 (11) | C201—C101—C301—C1 | −6.0 (3) |
C16A—C17A—C18—C20A | −3.3 (5) | N4—C108—C301—C101 | 3.8 (3) |
C16A—C17A—C18—C19 | 179.1 (3) | C208—C108—C301—C101 | −168.1 (2) |
C21A—C20A—C18—C17A | 3.8 (6) | N4—C108—C301—C1 | 174.58 (19) |
C21A—C20A—C18—C19 | −178.6 (3) | C208—C108—C301—C1 | 2.7 (3) |
C16B—C17B—C18—C20B | 16.8 (15) | C2—C1—C301—C101 | −63.6 (3) |
C16B—C17B—C18—C19 | −172.5 (8) | C7—C1—C301—C101 | 111.2 (3) |
C28—C22—C23—C24 | 1.6 (4) | C2—C1—C301—C108 | 125.2 (2) |
C304—C22—C23—C24 | −179.9 (2) | C7—C1—C301—C108 | −60.1 (3) |
C22—C23—C24—C25 | 0.6 (4) | N1—C102—C302—C103 | −3.6 (3) |
C23—C24—C25—C27 | −1.9 (4) | C202—C102—C302—C103 | 171.2 (2) |
C23—C24—C25—C26 | 176.9 (2) | N1—C102—C302—C8 | 179.2 (2) |
C24—C25—C27—C28 | 1.1 (4) | C202—C102—C302—C8 | −6.0 (3) |
C26—C25—C27—C28 | −177.8 (3) | N2—C103—C302—C102 | 9.7 (3) |
C23—C22—C28—C27 | −2.4 (4) | C203—C103—C302—C102 | −163.9 (2) |
C304—C22—C28—C27 | 179.1 (2) | N2—C103—C302—C8 | −173.1 (2) |
C25—C27—C28—C22 | 1.1 (4) | C203—C103—C302—C8 | 13.4 (3) |
C31—N5—C29—C30 | −0.4 (3) | C14—C8—C302—C102 | −97.3 (3) |
Fe1—N5—C29—C30 | 174.29 (19) | C9—C8—C302—C102 | 78.8 (3) |
N5—C29—C30—N6 | 0.6 (3) | C14—C8—C302—C103 | 85.3 (3) |
C31—N6—C30—C29 | −0.6 (3) | C9—C8—C302—C103 | −98.6 (3) |
C29—N5—C31—N6 | 0.0 (3) | N3—C105—C303—C104 | −7.3 (3) |
Fe1—N5—C31—N6 | −173.71 (16) | C205—C105—C303—C104 | 166.6 (2) |
C29—N5—C31—C32 | −178.4 (3) | N3—C105—C303—C15 | −179.31 (19) |
Fe1—N5—C31—C32 | 7.9 (4) | C205—C105—C303—C15 | −5.4 (3) |
C30—N6—C31—N5 | 0.4 (3) | N2—C104—C303—C105 | 3.1 (3) |
C30—N6—C31—C32 | 179.0 (3) | C204—C104—C303—C105 | −169.5 (2) |
C35—N7—C33—C34 | −0.1 (2) | N2—C104—C303—C15 | 175.08 (19) |
Fe1—N7—C33—C34 | −173.43 (15) | C204—C104—C303—C15 | 2.5 (3) |
N7—C33—C34—N8 | 0.4 (3) | C16B—C15—C303—C105 | −108.5 (8) |
C35—N8—C34—C33 | −0.5 (3) | C21B—C15—C303—C105 | 68.4 (9) |
C33—N7—C35—N8 | −0.3 (2) | C21A—C15—C303—C105 | 110.0 (3) |
Fe1—N7—C35—N8 | 171.86 (15) | C16A—C15—C303—C105 | −67.5 (3) |
C33—N7—C35—C36 | −179.5 (2) | C16B—C15—C303—C104 | 79.2 (8) |
Fe1—N7—C35—C36 | −7.4 (4) | C21B—C15—C303—C104 | −103.9 (9) |
C34—N8—C35—N7 | 0.5 (3) | C21A—C15—C303—C104 | −62.3 (3) |
C34—N8—C35—C36 | 179.8 (2) | C16A—C15—C303—C104 | 120.2 (3) |
C102—N1—C101—C301 | 172.2 (2) | N4—C107—C304—C106 | 8.8 (3) |
Fe1—N1—C101—C301 | −0.1 (3) | C207—C107—C304—C106 | −167.5 (2) |
C102—N1—C101—C201 | −0.9 (2) | N4—C107—C304—C22 | −176.28 (19) |
Fe1—N1—C101—C201 | −173.29 (14) | C207—C107—C304—C22 | 7.4 (3) |
C101—N1—C102—C302 | 175.2 (2) | N3—C106—C304—C107 | −7.0 (3) |
Fe1—N1—C102—C302 | −12.3 (3) | C206—C106—C304—C107 | 165.9 (2) |
C101—N1—C102—C202 | −0.3 (2) | N3—C106—C304—C22 | 178.18 (19) |
Fe1—N1—C102—C202 | 172.27 (14) | C206—C106—C304—C22 | −9.0 (3) |
C104—N2—C103—C302 | −174.2 (2) | C28—C22—C304—C107 | 79.0 (3) |
Fe1—N2—C103—C302 | 0.9 (3) | C23—C22—C304—C107 | −99.4 (3) |
C104—N2—C103—C203 | 0.2 (2) | C28—C22—C304—C106 | −105.8 (3) |
Fe1—N2—C103—C203 | 175.23 (14) | C23—C22—C304—C106 | 75.7 (3) |
C103—N2—C104—C303 | −172.1 (2) | C43—C41—C42—O6 | 32.1 (17) |
Fe1—N2—C104—C303 | 12.8 (3) | C44—O6—C42—C41 | −8.5 (19) |
C103—N2—C104—C204 | 1.4 (2) | C42—C41—C43—C44 | −43.7 (14) |
Fe1—N2—C104—C204 | −173.66 (14) | C41—C43—C44—O6 | 39.9 (15) |
C106—N3—C105—C303 | 174.41 (19) | C42—O6—C44—C43 | −19.3 (18) |
Fe1—N3—C105—C303 | −4.6 (3) | C40—O5—C37—C38 | −39.0 (4) |
C106—N3—C105—C205 | −0.3 (2) | O5—C37—C38—C39 | 26.3 (5) |
Fe1—N3—C105—C205 | −179.38 (14) | C37—C38—C39—C40 | −4.1 (5) |
C105—N3—C106—C304 | 172.64 (19) | C37—O5—C40—C39 | 35.8 (5) |
Fe1—N3—C106—C304 | −8.3 (3) | C38—C39—C40—O5 | −19.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6A···O3i | 0.81 (3) | 2.17 (3) | 2.942 (3) | 161 (3) |
N8—H8A···O2ii | 0.84 (3) | 2.11 (3) | 2.949 (3) | 176 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x, y, −z+1/2. |
Acknowledgements
We thank the CAS Hundred Talent Program and the National Natural Science Foundation of China (grant No. 21371167 to JL).
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