metal-organic compounds
Diaquabis(4-ferrocenyl-1,1,1-trifluoro-4-oxobutan-2-olato)cobalt(II)
aDepartment of Chemistry, Anhui University, Hefei, Anhui 230039, People's Republic of China
*Correspondence e-mail: 2438516329@qq.com
In the title compound, [CoFe2(C5H5)2(C9H5F3O2)2(H2O)2], the central Co atom has an octahedral coordination geometry defined by two chelating trifluoromethyl-β-diketone ferrocene ligands and two aqua ligands, with the latter in a cis disposition. The Cp rings in both ferrocene groupings are close to eclipsed. In the crystal, O—H⋯O hydrogen bonds link the molecules into [100] chains.
CCDC reference: 2031062
Structure description
β-Diketones are good chelating ligands for transition-metal ions and rare-earth metal ions and can possess pendant groups such as ferrocene. The resulting complexes may have applications in the fields of electroluminescent devices, environmental sensors, photodynamic therapy and biological imaging (e.g., Zheng et al., 2019). As part of our work in this area, we now describe the synthesis and structure of the title cobalt(II) complex.
The cobalt(II) atom has a octahedral coordination environment defined by two trifluoromethyl-β-diketone ferrocene ligands and two water ligands (Fig. 1) with the water molecules in a cis disposition: the dihedral angle between the carbon-atom skeletons of the diketone ligands is 81.73 (12)°. The Cp rings of both ferrocene groups are in nearly eclipsed conformations.
In the crystal, the molecules are linked into [100] chains by O—H⋯O hydrogen bonds arising from the water molecules (Table 1, Fig. 2); an intramolecular C—H⋯O and an intermolecular C—H⋯F link are also present. A short intermolecular F2⋯F6(1 − x, 1 − y, 1 − z) contact [2.783 (4) Å; van der Waals radius sum = 2.94 Å].
Synthesis and crystallization
In a 250 ml round-bottom flask, trifluoromethyl-β-diketone ferrocene (0.52 g 1.6 mmol), triethylamie (0.25 g 2.45 mmol) and cobalt acetate (0.13 g 0.5 mmol) were dissolved in 100 ml of methanol and the mixture was stirred at 343 K for 12 h and then cooled to room temperature. A red solid was obtained by suction filtration. Crystals for X-ray analysis were obtained by recrystallization from methanol solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 2031062
https://doi.org/10.1107/S2414314620012407/hb4360sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620012407/hb4360Isup3.hkl
Data collection: X-AREA (Stoe & Cie, 2018); cell
X-AREA (Stoe & Cie, 2018); data reduction: X-AREA (Stoe & Cie, 2018); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[CoFe2(C5H5)2(C9H5F3O2)2(H2O)2] | Z = 2 |
Mr = 741.10 | F(000) = 746 |
Triclinic, P1 | Dx = 1.847 Mg m−3 |
a = 7.725 (3) Å | Cu Kα radiation, λ = 1.54186 Å |
b = 12.721 (3) Å | Cell parameters from 1567 reflections |
c = 14.609 (4) Å | θ = 2.2–27.1° |
α = 70.67 (3)° | µ = 14.22 mm−1 |
β = 82.88 (3)° | T = 298 K |
γ = 80.46 (3)° | Block, black |
V = 1332.3 (8) Å3 | 0.30 × 0.20 × 0.10 mm |
Stoe Stadivari diffractometer | 3741 reflections with I > 2σ(I) |
Detector resolution: 5.81 pixels mm-1 | Rint = 0.031 |
rotation method, ω scans | θmax = 69.8°, θmin = 3.2° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2018) | h = −9→8 |
Tmin = 0.791, Tmax = 1 | k = −15→12 |
10376 measured reflections | l = −14→17 |
4786 independent reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0684P)2 + 2.1404P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4786 reflections | Δρmax = 0.88 e Å−3 |
404 parameters | Δρmin = −0.43 e Å−3 |
4 restraints |
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. The water H atoms were located in difference maps and their positions were freely refined. The C-bound H atoms were geometrically placed (C—H = 0.93 Å) and refined as riding atoms. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 1.04875 (9) | 0.97569 (6) | 0.25193 (5) | 0.01775 (18) | |
Co1 | 0.75176 (9) | 0.59847 (6) | 0.40437 (5) | 0.01579 (18) | |
Fe2 | 0.41805 (9) | 0.68982 (6) | 0.06889 (5) | 0.01960 (19) | |
F1 | 1.1799 (4) | 0.3465 (2) | 0.2975 (2) | 0.0325 (7) | |
O4 | 0.5761 (4) | 0.6874 (2) | 0.4767 (2) | 0.0187 (7) | |
O3 | 0.9383 (4) | 0.6985 (2) | 0.4060 (2) | 0.0169 (6) | |
O6 | 0.8032 (4) | 0.4822 (3) | 0.5508 (2) | 0.0187 (7) | |
O2 | 0.7000 (4) | 0.6910 (2) | 0.2635 (2) | 0.0184 (7) | |
F3 | 1.0466 (4) | 0.3623 (3) | 0.1729 (2) | 0.0385 (8) | |
O1 | 0.9307 (4) | 0.4897 (3) | 0.3551 (2) | 0.0194 (7) | |
O5 | 0.5584 (4) | 0.5023 (3) | 0.3964 (2) | 0.0198 (7) | |
F2 | 0.9375 (4) | 0.2795 (2) | 0.3160 (2) | 0.0413 (8) | |
F6 | 0.3060 (4) | 0.8234 (3) | 0.5387 (2) | 0.0476 (9) | |
F4 | 0.4611 (4) | 0.7265 (3) | 0.6544 (2) | 0.0484 (9) | |
F5 | 0.4848 (5) | 0.8988 (3) | 0.5881 (3) | 0.0724 (14) | |
C1 | 0.9093 (6) | 0.7927 (4) | 0.4211 (3) | 0.0163 (9) | |
C2 | 0.9182 (6) | 0.4767 (4) | 0.2728 (3) | 0.0183 (9) | |
C3 | 1.0453 (6) | 0.8669 (4) | 0.3887 (3) | 0.0172 (9) | |
C4 | 0.7257 (6) | 0.6514 (4) | 0.1939 (3) | 0.0191 (10) | |
C5 | 1.0342 (6) | 0.9798 (4) | 0.3894 (3) | 0.0202 (10) | |
H5 | 0.941577 | 1.017422 | 0.418284 | 0.024* | |
C6 | 1.2095 (6) | 0.8433 (4) | 0.3352 (3) | 0.0198 (10) | |
H6 | 1.251640 | 0.776175 | 0.322669 | 0.024* | |
C7 | 0.7500 (6) | 0.8293 (4) | 0.4712 (3) | 0.0202 (10) | |
H7 | 0.743876 | 0.895536 | 0.486151 | 0.024* | |
C8 | 1.1867 (6) | 1.0247 (4) | 0.3391 (3) | 0.0236 (10) | |
H8 | 1.212122 | 1.096675 | 0.329570 | 0.028* | |
C9 | 0.3371 (7) | 0.5597 (4) | 0.1828 (4) | 0.0262 (11) | |
H9 | 0.395210 | 0.524102 | 0.239319 | 0.031* | |
C10 | 0.4641 (6) | 0.8072 (4) | 0.5688 (3) | 0.0228 (10) | |
C11 | 1.2949 (6) | 0.9415 (4) | 0.3053 (3) | 0.0228 (10) | |
H11 | 1.403062 | 0.949758 | 0.269770 | 0.027* | |
C12 | 0.6081 (6) | 0.7719 (4) | 0.4979 (3) | 0.0177 (9) | |
C13 | 1.0207 (6) | 0.3657 (4) | 0.2642 (3) | 0.0233 (10) | |
C14 | 0.5571 (7) | 0.7789 (4) | −0.0537 (3) | 0.0265 (11) | |
H14 | 0.545588 | 0.783420 | −0.117552 | 0.032* | |
C15 | 0.6490 (6) | 0.7205 (4) | 0.1018 (3) | 0.0200 (10) | |
C16 | 0.5181 (6) | 0.8177 (4) | 0.0915 (3) | 0.0217 (10) | |
H16 | 0.477551 | 0.851307 | 0.139181 | 0.026* | |
C17 | 0.6710 (6) | 0.6982 (4) | 0.0107 (3) | 0.0237 (10) | |
H17 | 0.747661 | 0.640105 | −0.003396 | 0.028* | |
C18 | 0.8253 (6) | 0.5450 (4) | 0.1969 (3) | 0.0211 (10) | |
H18 | 0.826535 | 0.520855 | 0.143234 | 0.025* | |
C19 | 0.2517 (7) | 0.6062 (4) | 0.0283 (4) | 0.0298 (12) | |
H19 | 0.244149 | 0.606406 | −0.034824 | 0.036* | |
C20 | 0.3657 (7) | 0.5287 (4) | 0.0976 (4) | 0.0291 (11) | |
H20 | 0.444283 | 0.468764 | 0.088103 | 0.035* | |
C21 | 0.2064 (6) | 0.6533 (4) | 0.1682 (4) | 0.0274 (11) | |
H21 | 0.162300 | 0.689881 | 0.213413 | 0.033* | |
C22 | 0.1531 (7) | 0.6822 (4) | 0.0725 (4) | 0.0302 (12) | |
H22 | 0.067918 | 0.741102 | 0.044001 | 0.036* | |
C23 | 0.4620 (7) | 0.8529 (4) | −0.0039 (4) | 0.0279 (11) | |
H23 | 0.377786 | 0.913761 | −0.029743 | 0.034* | |
C24 | 1.0143 (9) | 0.9500 (5) | 0.1257 (4) | 0.0403 (15) | |
H24 | 1.073099 | 0.891183 | 0.104610 | 0.048* | |
C25 | 0.8582 (8) | 0.9484 (5) | 0.1816 (4) | 0.0435 (16) | |
H25 | 0.792024 | 0.888831 | 0.204026 | 0.052* | |
C26 | 0.8148 (8) | 1.0523 (6) | 0.1993 (4) | 0.0488 (18) | |
H26 | 0.716692 | 1.073614 | 0.236117 | 0.059* | |
C27 | 1.0699 (9) | 1.0535 (6) | 0.1059 (4) | 0.0450 (16) | |
H27 | 1.171731 | 1.076386 | 0.068628 | 0.054* | |
C28 | 0.9490 (10) | 1.1174 (5) | 0.1505 (4) | 0.0504 (19) | |
H28 | 0.955198 | 1.190510 | 0.148564 | 0.061* | |
H6A | 0.867 (6) | 0.417 (3) | 0.556 (4) | 0.036 (16)* | |
H5A | 0.445 (4) | 0.530 (5) | 0.403 (5) | 0.06 (2)* | |
H5B | 0.563 (7) | 0.434 (2) | 0.438 (3) | 0.037 (16)* | |
H6B | 0.847 (7) | 0.513 (5) | 0.588 (4) | 0.042 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0234 (4) | 0.0162 (4) | 0.0139 (4) | −0.0039 (3) | −0.0056 (3) | −0.0031 (3) |
Co1 | 0.0160 (4) | 0.0165 (4) | 0.0152 (4) | −0.0017 (3) | −0.0038 (3) | −0.0047 (3) |
Fe2 | 0.0224 (4) | 0.0207 (4) | 0.0158 (4) | −0.0050 (3) | −0.0057 (3) | −0.0033 (3) |
F1 | 0.0244 (15) | 0.0303 (16) | 0.0402 (17) | 0.0054 (12) | −0.0077 (13) | −0.0103 (13) |
O4 | 0.0176 (16) | 0.0186 (16) | 0.0195 (16) | −0.0010 (13) | −0.0026 (12) | −0.0057 (13) |
O3 | 0.0177 (15) | 0.0132 (15) | 0.0192 (16) | 0.0002 (12) | −0.0047 (12) | −0.0043 (13) |
O6 | 0.0207 (17) | 0.0171 (16) | 0.0180 (16) | 0.0002 (13) | −0.0062 (13) | −0.0048 (13) |
O2 | 0.0219 (16) | 0.0174 (15) | 0.0164 (16) | −0.0025 (13) | −0.0029 (13) | −0.0054 (13) |
F3 | 0.0487 (19) | 0.0396 (18) | 0.0304 (16) | 0.0089 (15) | −0.0063 (14) | −0.0211 (14) |
O1 | 0.0194 (16) | 0.0218 (16) | 0.0174 (16) | −0.0016 (13) | −0.0033 (13) | −0.0065 (13) |
O5 | 0.0191 (17) | 0.0212 (17) | 0.0193 (17) | −0.0050 (14) | −0.0031 (13) | −0.0050 (14) |
F2 | 0.0389 (18) | 0.0229 (16) | 0.060 (2) | −0.0096 (13) | 0.0134 (16) | −0.0146 (15) |
F6 | 0.0221 (16) | 0.088 (3) | 0.0292 (17) | 0.0146 (16) | −0.0079 (13) | −0.0228 (17) |
F4 | 0.0391 (19) | 0.068 (2) | 0.0193 (16) | 0.0164 (17) | −0.0001 (13) | −0.0002 (15) |
F5 | 0.063 (2) | 0.067 (3) | 0.114 (4) | −0.036 (2) | 0.053 (2) | −0.072 (3) |
C1 | 0.021 (2) | 0.017 (2) | 0.009 (2) | 0.0005 (18) | −0.0063 (17) | −0.0013 (17) |
C2 | 0.019 (2) | 0.020 (2) | 0.020 (2) | −0.0068 (19) | 0.0022 (18) | −0.0101 (19) |
C3 | 0.014 (2) | 0.022 (2) | 0.015 (2) | −0.0014 (18) | −0.0052 (17) | −0.0035 (18) |
C4 | 0.020 (2) | 0.022 (2) | 0.017 (2) | −0.0081 (19) | −0.0056 (18) | −0.0047 (19) |
C5 | 0.027 (2) | 0.020 (2) | 0.016 (2) | 0.0002 (19) | −0.0092 (19) | −0.0069 (19) |
C6 | 0.021 (2) | 0.022 (2) | 0.017 (2) | 0.0020 (19) | −0.0075 (18) | −0.0065 (19) |
C7 | 0.023 (2) | 0.019 (2) | 0.020 (2) | −0.0018 (19) | −0.0012 (18) | −0.0093 (19) |
C8 | 0.031 (3) | 0.021 (2) | 0.023 (2) | −0.010 (2) | −0.008 (2) | −0.006 (2) |
C9 | 0.033 (3) | 0.022 (2) | 0.022 (2) | −0.012 (2) | −0.005 (2) | 0.000 (2) |
C10 | 0.021 (2) | 0.024 (2) | 0.025 (3) | 0.000 (2) | −0.0023 (19) | −0.011 (2) |
C11 | 0.019 (2) | 0.032 (3) | 0.019 (2) | −0.008 (2) | −0.0031 (18) | −0.006 (2) |
C12 | 0.018 (2) | 0.016 (2) | 0.017 (2) | 0.0064 (18) | −0.0060 (18) | −0.0063 (18) |
C13 | 0.022 (2) | 0.025 (2) | 0.024 (2) | −0.003 (2) | 0.0011 (19) | −0.009 (2) |
C14 | 0.032 (3) | 0.029 (3) | 0.017 (2) | −0.010 (2) | −0.006 (2) | −0.001 (2) |
C15 | 0.021 (2) | 0.022 (2) | 0.018 (2) | −0.0063 (19) | −0.0060 (18) | −0.0040 (19) |
C16 | 0.027 (2) | 0.016 (2) | 0.022 (2) | −0.0074 (19) | −0.003 (2) | −0.0024 (19) |
C17 | 0.022 (2) | 0.031 (3) | 0.019 (2) | −0.009 (2) | −0.0016 (19) | −0.007 (2) |
C18 | 0.025 (2) | 0.023 (2) | 0.019 (2) | −0.0030 (19) | −0.0049 (19) | −0.010 (2) |
C19 | 0.034 (3) | 0.035 (3) | 0.024 (3) | −0.019 (2) | −0.007 (2) | −0.007 (2) |
C20 | 0.036 (3) | 0.022 (3) | 0.031 (3) | −0.011 (2) | −0.004 (2) | −0.007 (2) |
C21 | 0.026 (3) | 0.034 (3) | 0.023 (2) | −0.013 (2) | 0.002 (2) | −0.008 (2) |
C22 | 0.028 (3) | 0.035 (3) | 0.027 (3) | −0.008 (2) | −0.008 (2) | −0.004 (2) |
C23 | 0.030 (3) | 0.021 (2) | 0.027 (3) | −0.010 (2) | −0.012 (2) | 0.007 (2) |
C24 | 0.070 (4) | 0.030 (3) | 0.022 (3) | 0.017 (3) | −0.026 (3) | −0.014 (2) |
C25 | 0.051 (4) | 0.045 (4) | 0.033 (3) | −0.024 (3) | −0.028 (3) | 0.008 (3) |
C26 | 0.030 (3) | 0.081 (5) | 0.024 (3) | 0.019 (3) | −0.014 (2) | −0.010 (3) |
C27 | 0.053 (4) | 0.058 (4) | 0.019 (3) | −0.021 (3) | −0.009 (3) | 0.003 (3) |
C28 | 0.102 (6) | 0.018 (3) | 0.035 (3) | 0.000 (3) | −0.047 (4) | −0.002 (2) |
Fe1—C3 | 2.019 (4) | C3—C5 | 1.428 (6) |
Fe1—C5 | 2.015 (4) | C3—C6 | 1.446 (6) |
Fe1—C6 | 2.046 (4) | C4—C15 | 1.475 (6) |
Fe1—C8 | 2.056 (5) | C4—C18 | 1.431 (6) |
Fe1—C11 | 2.069 (5) | C5—H5 | 0.9300 |
Fe1—C24 | 2.032 (5) | C5—C8 | 1.409 (7) |
Fe1—C25 | 2.031 (5) | C6—H6 | 0.9300 |
Fe1—C26 | 2.018 (5) | C6—C11 | 1.424 (7) |
Fe1—C27 | 2.032 (5) | C7—H7 | 0.9300 |
Fe1—C28 | 2.024 (5) | C7—C12 | 1.363 (6) |
Co1—O4 | 2.042 (3) | C8—H8 | 0.9300 |
Co1—O3 | 2.082 (3) | C8—C11 | 1.418 (7) |
Co1—O6 | 2.200 (3) | C9—H9 | 0.9300 |
Co1—O2 | 2.056 (3) | C9—C20 | 1.408 (7) |
Co1—O1 | 2.031 (3) | C9—C21 | 1.404 (7) |
Co1—O5 | 2.117 (3) | C10—C12 | 1.540 (6) |
Fe2—C9 | 2.040 (5) | C11—H11 | 0.9300 |
Fe2—C14 | 2.056 (5) | C14—H14 | 0.9300 |
Fe2—C15 | 2.033 (4) | C14—C17 | 1.408 (7) |
Fe2—C16 | 2.046 (4) | C14—C23 | 1.431 (7) |
Fe2—C17 | 2.037 (5) | C15—C16 | 1.440 (7) |
Fe2—C19 | 2.048 (5) | C15—C17 | 1.434 (6) |
Fe2—C20 | 2.050 (5) | C16—H16 | 0.9300 |
Fe2—C21 | 2.052 (5) | C16—C23 | 1.415 (7) |
Fe2—C22 | 2.059 (5) | C17—H17 | 0.9300 |
Fe2—C23 | 2.058 (5) | C18—H18 | 0.9300 |
F1—C13 | 1.334 (5) | C19—H19 | 0.9300 |
O4—C12 | 1.280 (5) | C19—C20 | 1.430 (7) |
O3—C1 | 1.267 (5) | C19—C22 | 1.407 (8) |
O6—H6A | 0.88 (2) | C20—H20 | 0.9300 |
O6—H6B | 0.89 (2) | C21—H21 | 0.9300 |
O2—C4 | 1.258 (5) | C21—C22 | 1.418 (7) |
F3—C13 | 1.338 (5) | C22—H22 | 0.9300 |
O1—C2 | 1.283 (5) | C23—H23 | 0.9300 |
O5—H5A | 0.89 (2) | C24—H24 | 0.9300 |
O5—H5B | 0.88 (2) | C24—C25 | 1.369 (9) |
F2—C13 | 1.324 (6) | C24—C27 | 1.381 (8) |
F6—C10 | 1.310 (6) | C25—H25 | 0.9300 |
F4—C10 | 1.330 (6) | C25—C26 | 1.409 (9) |
F5—C10 | 1.323 (6) | C26—H26 | 0.9300 |
C1—C3 | 1.459 (6) | C26—C28 | 1.408 (10) |
C1—C7 | 1.442 (6) | C27—H27 | 0.9300 |
C2—C13 | 1.536 (6) | C27—C28 | 1.380 (9) |
C2—C18 | 1.362 (6) | C28—H28 | 0.9300 |
C3—Fe1—C6 | 41.69 (17) | C8—C5—Fe1 | 71.3 (3) |
C3—Fe1—C8 | 68.92 (18) | C8—C5—C3 | 108.7 (4) |
C3—Fe1—C11 | 68.98 (17) | C8—C5—H5 | 125.6 |
C3—Fe1—C24 | 129.2 (2) | Fe1—C6—H6 | 126.5 |
C3—Fe1—C25 | 108.7 (2) | C3—C6—Fe1 | 68.2 (2) |
C3—Fe1—C27 | 167.1 (2) | C3—C6—H6 | 126.2 |
C3—Fe1—C28 | 151.3 (3) | C11—C6—Fe1 | 70.6 (3) |
C5—Fe1—C3 | 41.46 (18) | C11—C6—C3 | 107.5 (4) |
C5—Fe1—C6 | 69.37 (18) | C11—C6—H6 | 126.2 |
C5—Fe1—C8 | 40.50 (19) | C1—C7—H7 | 118.3 |
C5—Fe1—C11 | 68.30 (19) | C12—C7—C1 | 123.4 (4) |
C5—Fe1—C24 | 166.2 (2) | C12—C7—H7 | 118.3 |
C5—Fe1—C25 | 128.1 (2) | Fe1—C8—H8 | 127.2 |
C5—Fe1—C26 | 106.1 (2) | C5—C8—Fe1 | 68.2 (2) |
C5—Fe1—C27 | 150.9 (2) | C5—C8—H8 | 125.8 |
C5—Fe1—C28 | 116.8 (2) | C5—C8—C11 | 108.4 (4) |
C6—Fe1—C8 | 68.35 (19) | C11—C8—Fe1 | 70.4 (3) |
C6—Fe1—C11 | 40.50 (18) | C11—C8—H8 | 125.8 |
C8—Fe1—C11 | 40.20 (19) | Fe2—C9—H9 | 125.2 |
C24—Fe1—C6 | 110.3 (2) | C20—C9—Fe2 | 70.3 (3) |
C24—Fe1—C8 | 153.1 (2) | C20—C9—H9 | 125.7 |
C24—Fe1—C11 | 121.0 (2) | C21—C9—Fe2 | 70.4 (3) |
C25—Fe1—C6 | 120.4 (2) | C21—C9—H9 | 125.7 |
C25—Fe1—C8 | 165.0 (3) | C21—C9—C20 | 108.6 (4) |
C25—Fe1—C11 | 154.1 (2) | F6—C10—F4 | 106.0 (4) |
C25—Fe1—C24 | 39.4 (3) | F6—C10—F5 | 107.2 (4) |
C25—Fe1—C27 | 66.7 (2) | F6—C10—C12 | 112.6 (4) |
C26—Fe1—C3 | 117.4 (2) | F4—C10—C12 | 110.2 (4) |
C26—Fe1—C6 | 153.2 (3) | F5—C10—F4 | 105.5 (4) |
C26—Fe1—C8 | 126.1 (2) | F5—C10—C12 | 114.9 (4) |
C26—Fe1—C11 | 164.1 (3) | Fe1—C11—H11 | 127.5 |
C26—Fe1—C24 | 67.6 (2) | C6—C11—Fe1 | 68.9 (2) |
C26—Fe1—C25 | 40.7 (3) | C6—C11—H11 | 125.8 |
C26—Fe1—C27 | 67.6 (3) | C8—C11—Fe1 | 69.4 (3) |
C26—Fe1—C28 | 40.8 (3) | C8—C11—C6 | 108.3 (4) |
C27—Fe1—C6 | 129.1 (2) | C8—C11—H11 | 125.8 |
C27—Fe1—C8 | 118.8 (2) | O4—C12—C7 | 130.3 (4) |
C27—Fe1—C11 | 109.6 (2) | O4—C12—C10 | 112.4 (4) |
C27—Fe1—C24 | 39.7 (2) | C7—C12—C10 | 117.3 (4) |
C28—Fe1—C6 | 165.2 (3) | F1—C13—F3 | 106.3 (4) |
C28—Fe1—C8 | 106.9 (2) | F1—C13—C2 | 111.4 (4) |
C28—Fe1—C11 | 127.1 (2) | F3—C13—C2 | 113.7 (4) |
C28—Fe1—C24 | 67.2 (2) | F2—C13—F1 | 106.9 (4) |
C28—Fe1—C25 | 67.7 (2) | F2—C13—F3 | 107.2 (4) |
C28—Fe1—C27 | 39.8 (3) | F2—C13—C2 | 110.9 (4) |
O4—Co1—O3 | 88.20 (12) | Fe2—C14—H14 | 126.8 |
O4—Co1—O6 | 84.49 (12) | C17—C14—Fe2 | 69.1 (3) |
O4—Co1—O2 | 99.68 (12) | C17—C14—H14 | 125.9 |
O4—Co1—O5 | 91.75 (12) | C17—C14—C23 | 108.1 (4) |
O3—Co1—O6 | 93.19 (11) | C23—C14—Fe2 | 69.7 (3) |
O3—Co1—O5 | 177.31 (12) | C23—C14—H14 | 125.9 |
O2—Co1—O3 | 92.11 (12) | C4—C15—Fe2 | 120.1 (3) |
O2—Co1—O6 | 173.36 (12) | C16—C15—Fe2 | 69.8 (3) |
O2—Co1—O5 | 85.25 (12) | C16—C15—C4 | 124.5 (4) |
O1—Co1—O4 | 170.17 (12) | C17—C15—Fe2 | 69.5 (3) |
O1—Co1—O3 | 93.61 (12) | C17—C15—C4 | 128.0 (4) |
O1—Co1—O6 | 85.76 (12) | C17—C15—C16 | 107.1 (4) |
O1—Co1—O2 | 89.91 (12) | Fe2—C16—H16 | 126.4 |
O1—Co1—O5 | 86.89 (13) | C15—C16—Fe2 | 68.8 (2) |
O5—Co1—O6 | 89.48 (12) | C15—C16—H16 | 126.0 |
C9—Fe2—C14 | 161.3 (2) | C23—C16—Fe2 | 70.3 (3) |
C9—Fe2—C16 | 121.12 (19) | C23—C16—C15 | 108.0 (4) |
C9—Fe2—C19 | 68.09 (19) | C23—C16—H16 | 126.0 |
C9—Fe2—C20 | 40.3 (2) | Fe2—C17—H17 | 126.0 |
C9—Fe2—C21 | 40.1 (2) | C14—C17—Fe2 | 70.6 (3) |
C9—Fe2—C22 | 67.8 (2) | C14—C17—C15 | 108.6 (4) |
C9—Fe2—C23 | 156.4 (2) | C14—C17—H17 | 125.7 |
C14—Fe2—C22 | 122.4 (2) | C15—C17—Fe2 | 69.2 (3) |
C14—Fe2—C23 | 40.7 (2) | C15—C17—H17 | 125.7 |
C15—Fe2—C9 | 106.95 (19) | C2—C18—C4 | 124.5 (4) |
C15—Fe2—C14 | 68.69 (18) | C2—C18—H18 | 117.7 |
C15—Fe2—C16 | 41.35 (18) | C4—C18—H18 | 117.7 |
C15—Fe2—C17 | 41.26 (18) | Fe2—C19—H19 | 125.5 |
C15—Fe2—C19 | 157.4 (2) | C20—C19—Fe2 | 69.7 (3) |
C15—Fe2—C20 | 121.1 (2) | C20—C19—H19 | 126.1 |
C15—Fe2—C21 | 123.60 (19) | C22—C19—Fe2 | 70.4 (3) |
C15—Fe2—C22 | 160.5 (2) | C22—C19—H19 | 126.1 |
C15—Fe2—C23 | 68.74 (19) | C22—C19—C20 | 107.8 (4) |
C16—Fe2—C14 | 68.40 (19) | Fe2—C20—H20 | 126.4 |
C16—Fe2—C19 | 160.3 (2) | C9—C20—Fe2 | 69.5 (3) |
C16—Fe2—C20 | 156.71 (19) | C9—C20—C19 | 107.5 (5) |
C16—Fe2—C21 | 107.2 (2) | C9—C20—H20 | 126.3 |
C16—Fe2—C22 | 123.9 (2) | C19—C20—Fe2 | 69.5 (3) |
C16—Fe2—C23 | 40.34 (18) | C19—C20—H20 | 126.3 |
C17—Fe2—C9 | 124.7 (2) | Fe2—C21—H21 | 126.1 |
C17—Fe2—C14 | 40.23 (19) | C9—C21—Fe2 | 69.5 (3) |
C17—Fe2—C16 | 69.0 (2) | C9—C21—H21 | 125.9 |
C17—Fe2—C19 | 122.1 (2) | C9—C21—C22 | 108.1 (5) |
C17—Fe2—C20 | 108.1 (2) | C22—C21—Fe2 | 70.1 (3) |
C17—Fe2—C21 | 160.95 (19) | C22—C21—H21 | 125.9 |
C17—Fe2—C22 | 157.2 (2) | Fe2—C22—H22 | 126.4 |
C17—Fe2—C23 | 68.3 (2) | C19—C22—Fe2 | 69.5 (3) |
C19—Fe2—C14 | 108.5 (2) | C19—C22—C21 | 107.9 (5) |
C19—Fe2—C20 | 40.9 (2) | C19—C22—H22 | 126.0 |
C19—Fe2—C21 | 67.7 (2) | C21—C22—Fe2 | 69.6 (3) |
C19—Fe2—C22 | 40.1 (2) | C21—C22—H22 | 126.0 |
C19—Fe2—C23 | 124.7 (2) | Fe2—C23—H23 | 126.7 |
C20—Fe2—C14 | 125.2 (2) | C14—C23—Fe2 | 69.6 (3) |
C20—Fe2—C21 | 67.6 (2) | C14—C23—H23 | 125.9 |
C20—Fe2—C22 | 67.9 (2) | C16—C23—Fe2 | 69.4 (3) |
C20—Fe2—C23 | 161.9 (2) | C16—C23—C14 | 108.2 (4) |
C21—Fe2—C14 | 157.4 (2) | C16—C23—H23 | 125.9 |
C21—Fe2—C22 | 40.35 (19) | Fe1—C24—H24 | 125.4 |
C21—Fe2—C23 | 121.6 (2) | C25—C24—Fe1 | 70.3 (3) |
C23—Fe2—C22 | 108.1 (2) | C25—C24—H24 | 125.7 |
C12—O4—Co1 | 124.6 (3) | C25—C24—C27 | 108.5 (5) |
C1—O3—Co1 | 127.0 (3) | C27—C24—Fe1 | 70.1 (3) |
Co1—O6—H6A | 118 (4) | C27—C24—H24 | 125.7 |
Co1—O6—H6B | 114 (4) | Fe1—C25—H25 | 126.3 |
H6A—O6—H6B | 108 (5) | C24—C25—Fe1 | 70.4 (3) |
C4—O2—Co1 | 123.8 (3) | C24—C25—H25 | 125.8 |
C2—O1—Co1 | 120.9 (3) | C24—C25—C26 | 108.4 (5) |
Co1—O5—H5A | 119 (4) | C26—C25—Fe1 | 69.1 (3) |
Co1—O5—H5B | 116 (4) | C26—C25—H25 | 125.8 |
H5A—O5—H5B | 103 (6) | Fe1—C26—H26 | 124.9 |
O3—C1—C3 | 118.7 (4) | C25—C26—Fe1 | 70.2 (3) |
O3—C1—C7 | 123.3 (4) | C25—C26—H26 | 126.7 |
C7—C1—C3 | 118.0 (4) | C28—C26—Fe1 | 69.8 (3) |
O1—C2—C13 | 112.7 (4) | C28—C26—C25 | 106.6 (6) |
O1—C2—C18 | 129.0 (4) | C28—C26—H26 | 126.7 |
C18—C2—C13 | 118.2 (4) | Fe1—C27—H27 | 126.0 |
C1—C3—Fe1 | 118.9 (3) | C24—C27—Fe1 | 70.1 (3) |
C5—C3—Fe1 | 69.1 (2) | C24—C27—H27 | 125.7 |
C5—C3—C1 | 128.0 (4) | C28—C27—Fe1 | 69.8 (3) |
C5—C3—C6 | 107.0 (4) | C28—C27—C24 | 108.7 (6) |
C6—C3—Fe1 | 70.1 (2) | C28—C27—H27 | 125.7 |
C6—C3—C1 | 124.4 (4) | Fe1—C28—H28 | 125.7 |
O2—C4—C15 | 117.4 (4) | C26—C28—Fe1 | 69.4 (3) |
O2—C4—C18 | 125.1 (4) | C26—C28—H28 | 126.1 |
C18—C4—C15 | 117.5 (4) | C27—C28—Fe1 | 70.4 (3) |
Fe1—C5—H5 | 125.2 | C27—C28—C26 | 107.8 (5) |
C3—C5—Fe1 | 69.4 (2) | C27—C28—H28 | 126.1 |
C3—C5—H5 | 125.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O6i | 0.89 (4) | 1.97 (4) | 2.797 (5) | 154 (6) |
O5—H5B···O4i | 0.88 (4) | 2.01 (4) | 2.781 (4) | 146 (5) |
O6—H6A···O3ii | 0.88 (4) | 1.91 (5) | 2.739 (5) | 156 (4) |
O6—H6B···O1ii | 0.89 (6) | 1.99 (6) | 2.741 (5) | 141 (5) |
C25—H25···O2 | 0.93 | 2.57 | 3.467 (7) | 163 |
C28—H28···F3iii | 0.93 | 2.55 | 3.449 (8) | 163 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y+1, z. |
Funding information
Funding for this research was provided by: National Nature Science Foundation of China (award Nos. 21871003 and 51672002).
References
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