metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

Di­aqua­bis­­(4-ferrocenyl-1,1,1-tri­fluoro-4-oxobutan-2-olato)cobalt(II)

CROSSMARK_Color_square_no_text.svg

aDepartment of Chemistry, Anhui University, Hefei, Anhui 230039, People's Republic of China
*Correspondence e-mail: 2438516329@qq.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 August 2020; accepted 9 September 2020; online 11 September 2020)

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[Zheng, Z., Li, D. Y., Liu, Z. Y., Peng, H., Sung, H. H. Y., Kwok, R. T. K., Williams, I. D., Lam, J. W. Y., Qian, J. & Tang, B. Z. (2019). Adv. Mater. 31, 1904799.]). 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[link]) 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.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level; H atoms are omitted for clarity.

In the crystal, the mol­ecules are linked into [100] chains by O—H⋯O hydrogen bonds arising from the water mol­ecules (Table 1[link], Fig. 2[link]); 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].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.
[Figure 2]
Figure 2
Partial packing diagram of the title compound showing significant H⋯F and F⋯F contacts involving the C10/F4/F5/F6 group as dashed lines.

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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula [CoFe2(C5H5)2(C9H5F3O2)2(H2O)2]
Mr 741.10
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 298
a, b, c (Å) 7.725 (3), 12.721 (3), 14.609 (4)
α, β, γ (°) 70.67 (3), 82.88 (3), 80.46 (3)
V3) 1332.3 (8)
Z 2
Radiation type Cu Kα
μ (mm−1) 14.22
Crystal size (mm) 0.30 × 0.20 × 0.10
 
Data collection
Diffractometer Stoe Stadivari
Absorption correction Multi-scan (X-AREA; Stoe & Cie, 2018[Stoe & Cie (2018). X-AREA. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.791, 1
No. of measured, independent and observed [I > 2σ(I)] reflections 10376, 4786, 3741
Rint 0.031
(sin θ/λ)max−1) 0.609
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.127, 1.05
No. of reflections 4786
No. of parameters 404
No. of restraints 4
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.88, −0.43
Computer programs: X-AREA (Stoe & Cie, 2018[Stoe & Cie (2018). X-AREA. Stoe & Cie, Darmstadt, Germany.]), olex2.solve (Bourhis et al., 2015[Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59-75.]), SHELXL (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: X-AREA (Stoe & Cie, 2018); cell refinement: 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).

Diaquabis(4-ferrocenyl-1,1,1-trifluoro-4-oxobutan-2-olato)cobalt(II) top
Crystal data top
[CoFe2(C5H5)2(C9H5F3O2)2(H2O)2]Z = 2
Mr = 741.10F(000) = 746
Triclinic, P1Dx = 1.847 Mg m3
a = 7.725 (3) ÅCu Kα radiation, λ = 1.54186 Å
b = 12.721 (3) ÅCell parameters from 1567 reflections
c = 14.609 (4) Åθ = 2.2–27.1°
α = 70.67 (3)°µ = 14.22 mm1
β = 82.88 (3)°T = 298 K
γ = 80.46 (3)°Block, black
V = 1332.3 (8) Å30.30 × 0.20 × 0.10 mm
Data collection top
Stoe Stadivari
diffractometer
3741 reflections with I > 2σ(I)
Detector resolution: 5.81 pixels mm-1Rint = 0.031
rotation method, ω scansθmax = 69.8°, θmin = 3.2°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2018)
h = 98
Tmin = 0.791, Tmax = 1k = 1512
10376 measured reflectionsl = 1417
4786 independent reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049H 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 reflectionsΔρmax = 0.88 e Å3
404 parametersΔρmin = 0.43 e Å3
4 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe11.04875 (9)0.97569 (6)0.25193 (5)0.01775 (18)
Co10.75176 (9)0.59847 (6)0.40437 (5)0.01579 (18)
Fe20.41805 (9)0.68982 (6)0.06889 (5)0.01960 (19)
F11.1799 (4)0.3465 (2)0.2975 (2)0.0325 (7)
O40.5761 (4)0.6874 (2)0.4767 (2)0.0187 (7)
O30.9383 (4)0.6985 (2)0.4060 (2)0.0169 (6)
O60.8032 (4)0.4822 (3)0.5508 (2)0.0187 (7)
O20.7000 (4)0.6910 (2)0.2635 (2)0.0184 (7)
F31.0466 (4)0.3623 (3)0.1729 (2)0.0385 (8)
O10.9307 (4)0.4897 (3)0.3551 (2)0.0194 (7)
O50.5584 (4)0.5023 (3)0.3964 (2)0.0198 (7)
F20.9375 (4)0.2795 (2)0.3160 (2)0.0413 (8)
F60.3060 (4)0.8234 (3)0.5387 (2)0.0476 (9)
F40.4611 (4)0.7265 (3)0.6544 (2)0.0484 (9)
F50.4848 (5)0.8988 (3)0.5881 (3)0.0724 (14)
C10.9093 (6)0.7927 (4)0.4211 (3)0.0163 (9)
C20.9182 (6)0.4767 (4)0.2728 (3)0.0183 (9)
C31.0453 (6)0.8669 (4)0.3887 (3)0.0172 (9)
C40.7257 (6)0.6514 (4)0.1939 (3)0.0191 (10)
C51.0342 (6)0.9798 (4)0.3894 (3)0.0202 (10)
H50.9415771.0174220.4182840.024*
C61.2095 (6)0.8433 (4)0.3352 (3)0.0198 (10)
H61.2516400.7761750.3226690.024*
C70.7500 (6)0.8293 (4)0.4712 (3)0.0202 (10)
H70.7438760.8955360.4861510.024*
C81.1867 (6)1.0247 (4)0.3391 (3)0.0236 (10)
H81.2121221.0966750.3295700.028*
C90.3371 (7)0.5597 (4)0.1828 (4)0.0262 (11)
H90.3952100.5241020.2393190.031*
C100.4641 (6)0.8072 (4)0.5688 (3)0.0228 (10)
C111.2949 (6)0.9415 (4)0.3053 (3)0.0228 (10)
H111.4030620.9497580.2697700.027*
C120.6081 (6)0.7719 (4)0.4979 (3)0.0177 (9)
C131.0207 (6)0.3657 (4)0.2642 (3)0.0233 (10)
C140.5571 (7)0.7789 (4)0.0537 (3)0.0265 (11)
H140.5455880.7834200.1175520.032*
C150.6490 (6)0.7205 (4)0.1018 (3)0.0200 (10)
C160.5181 (6)0.8177 (4)0.0915 (3)0.0217 (10)
H160.4775510.8513070.1391810.026*
C170.6710 (6)0.6982 (4)0.0107 (3)0.0237 (10)
H170.7476610.6401050.0033960.028*
C180.8253 (6)0.5450 (4)0.1969 (3)0.0211 (10)
H180.8265350.5208550.1432340.025*
C190.2517 (7)0.6062 (4)0.0283 (4)0.0298 (12)
H190.2441490.6064060.0348240.036*
C200.3657 (7)0.5287 (4)0.0976 (4)0.0291 (11)
H200.4442830.4687640.0881030.035*
C210.2064 (6)0.6533 (4)0.1682 (4)0.0274 (11)
H210.1623000.6898810.2134130.033*
C220.1531 (7)0.6822 (4)0.0725 (4)0.0302 (12)
H220.0679180.7411020.0440010.036*
C230.4620 (7)0.8529 (4)0.0039 (4)0.0279 (11)
H230.3777860.9137610.0297430.034*
C241.0143 (9)0.9500 (5)0.1257 (4)0.0403 (15)
H241.0730990.8911830.1046100.048*
C250.8582 (8)0.9484 (5)0.1816 (4)0.0435 (16)
H250.7920240.8888310.2040260.052*
C260.8148 (8)1.0523 (6)0.1993 (4)0.0488 (18)
H260.7166921.0736140.2361170.059*
C271.0699 (9)1.0535 (6)0.1059 (4)0.0450 (16)
H271.1717311.0763860.0686280.054*
C280.9490 (10)1.1174 (5)0.1505 (4)0.0504 (19)
H280.9551981.1905100.1485640.061*
H6A0.867 (6)0.417 (3)0.556 (4)0.036 (16)*
H5A0.445 (4)0.530 (5)0.403 (5)0.06 (2)*
H5B0.563 (7)0.434 (2)0.438 (3)0.037 (16)*
H6B0.847 (7)0.513 (5)0.588 (4)0.042 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0234 (4)0.0162 (4)0.0139 (4)0.0039 (3)0.0056 (3)0.0031 (3)
Co10.0160 (4)0.0165 (4)0.0152 (4)0.0017 (3)0.0038 (3)0.0047 (3)
Fe20.0224 (4)0.0207 (4)0.0158 (4)0.0050 (3)0.0057 (3)0.0033 (3)
F10.0244 (15)0.0303 (16)0.0402 (17)0.0054 (12)0.0077 (13)0.0103 (13)
O40.0176 (16)0.0186 (16)0.0195 (16)0.0010 (13)0.0026 (12)0.0057 (13)
O30.0177 (15)0.0132 (15)0.0192 (16)0.0002 (12)0.0047 (12)0.0043 (13)
O60.0207 (17)0.0171 (16)0.0180 (16)0.0002 (13)0.0062 (13)0.0048 (13)
O20.0219 (16)0.0174 (15)0.0164 (16)0.0025 (13)0.0029 (13)0.0054 (13)
F30.0487 (19)0.0396 (18)0.0304 (16)0.0089 (15)0.0063 (14)0.0211 (14)
O10.0194 (16)0.0218 (16)0.0174 (16)0.0016 (13)0.0033 (13)0.0065 (13)
O50.0191 (17)0.0212 (17)0.0193 (17)0.0050 (14)0.0031 (13)0.0050 (14)
F20.0389 (18)0.0229 (16)0.060 (2)0.0096 (13)0.0134 (16)0.0146 (15)
F60.0221 (16)0.088 (3)0.0292 (17)0.0146 (16)0.0079 (13)0.0228 (17)
F40.0391 (19)0.068 (2)0.0193 (16)0.0164 (17)0.0001 (13)0.0002 (15)
F50.063 (2)0.067 (3)0.114 (4)0.036 (2)0.053 (2)0.072 (3)
C10.021 (2)0.017 (2)0.009 (2)0.0005 (18)0.0063 (17)0.0013 (17)
C20.019 (2)0.020 (2)0.020 (2)0.0068 (19)0.0022 (18)0.0101 (19)
C30.014 (2)0.022 (2)0.015 (2)0.0014 (18)0.0052 (17)0.0035 (18)
C40.020 (2)0.022 (2)0.017 (2)0.0081 (19)0.0056 (18)0.0047 (19)
C50.027 (2)0.020 (2)0.016 (2)0.0002 (19)0.0092 (19)0.0069 (19)
C60.021 (2)0.022 (2)0.017 (2)0.0020 (19)0.0075 (18)0.0065 (19)
C70.023 (2)0.019 (2)0.020 (2)0.0018 (19)0.0012 (18)0.0093 (19)
C80.031 (3)0.021 (2)0.023 (2)0.010 (2)0.008 (2)0.006 (2)
C90.033 (3)0.022 (2)0.022 (2)0.012 (2)0.005 (2)0.000 (2)
C100.021 (2)0.024 (2)0.025 (3)0.000 (2)0.0023 (19)0.011 (2)
C110.019 (2)0.032 (3)0.019 (2)0.008 (2)0.0031 (18)0.006 (2)
C120.018 (2)0.016 (2)0.017 (2)0.0064 (18)0.0060 (18)0.0063 (18)
C130.022 (2)0.025 (2)0.024 (2)0.003 (2)0.0011 (19)0.009 (2)
C140.032 (3)0.029 (3)0.017 (2)0.010 (2)0.006 (2)0.001 (2)
C150.021 (2)0.022 (2)0.018 (2)0.0063 (19)0.0060 (18)0.0040 (19)
C160.027 (2)0.016 (2)0.022 (2)0.0074 (19)0.003 (2)0.0024 (19)
C170.022 (2)0.031 (3)0.019 (2)0.009 (2)0.0016 (19)0.007 (2)
C180.025 (2)0.023 (2)0.019 (2)0.0030 (19)0.0049 (19)0.010 (2)
C190.034 (3)0.035 (3)0.024 (3)0.019 (2)0.007 (2)0.007 (2)
C200.036 (3)0.022 (3)0.031 (3)0.011 (2)0.004 (2)0.007 (2)
C210.026 (3)0.034 (3)0.023 (2)0.013 (2)0.002 (2)0.008 (2)
C220.028 (3)0.035 (3)0.027 (3)0.008 (2)0.008 (2)0.004 (2)
C230.030 (3)0.021 (2)0.027 (3)0.010 (2)0.012 (2)0.007 (2)
C240.070 (4)0.030 (3)0.022 (3)0.017 (3)0.026 (3)0.014 (2)
C250.051 (4)0.045 (4)0.033 (3)0.024 (3)0.028 (3)0.008 (3)
C260.030 (3)0.081 (5)0.024 (3)0.019 (3)0.014 (2)0.010 (3)
C270.053 (4)0.058 (4)0.019 (3)0.021 (3)0.009 (3)0.003 (3)
C280.102 (6)0.018 (3)0.035 (3)0.000 (3)0.047 (4)0.002 (2)
Geometric parameters (Å, º) top
Fe1—C32.019 (4)C3—C51.428 (6)
Fe1—C52.015 (4)C3—C61.446 (6)
Fe1—C62.046 (4)C4—C151.475 (6)
Fe1—C82.056 (5)C4—C181.431 (6)
Fe1—C112.069 (5)C5—H50.9300
Fe1—C242.032 (5)C5—C81.409 (7)
Fe1—C252.031 (5)C6—H60.9300
Fe1—C262.018 (5)C6—C111.424 (7)
Fe1—C272.032 (5)C7—H70.9300
Fe1—C282.024 (5)C7—C121.363 (6)
Co1—O42.042 (3)C8—H80.9300
Co1—O32.082 (3)C8—C111.418 (7)
Co1—O62.200 (3)C9—H90.9300
Co1—O22.056 (3)C9—C201.408 (7)
Co1—O12.031 (3)C9—C211.404 (7)
Co1—O52.117 (3)C10—C121.540 (6)
Fe2—C92.040 (5)C11—H110.9300
Fe2—C142.056 (5)C14—H140.9300
Fe2—C152.033 (4)C14—C171.408 (7)
Fe2—C162.046 (4)C14—C231.431 (7)
Fe2—C172.037 (5)C15—C161.440 (7)
Fe2—C192.048 (5)C15—C171.434 (6)
Fe2—C202.050 (5)C16—H160.9300
Fe2—C212.052 (5)C16—C231.415 (7)
Fe2—C222.059 (5)C17—H170.9300
Fe2—C232.058 (5)C18—H180.9300
F1—C131.334 (5)C19—H190.9300
O4—C121.280 (5)C19—C201.430 (7)
O3—C11.267 (5)C19—C221.407 (8)
O6—H6A0.88 (2)C20—H200.9300
O6—H6B0.89 (2)C21—H210.9300
O2—C41.258 (5)C21—C221.418 (7)
F3—C131.338 (5)C22—H220.9300
O1—C21.283 (5)C23—H230.9300
O5—H5A0.89 (2)C24—H240.9300
O5—H5B0.88 (2)C24—C251.369 (9)
F2—C131.324 (6)C24—C271.381 (8)
F6—C101.310 (6)C25—H250.9300
F4—C101.330 (6)C25—C261.409 (9)
F5—C101.323 (6)C26—H260.9300
C1—C31.459 (6)C26—C281.408 (10)
C1—C71.442 (6)C27—H270.9300
C2—C131.536 (6)C27—C281.380 (9)
C2—C181.362 (6)C28—H280.9300
C3—Fe1—C641.69 (17)C8—C5—Fe171.3 (3)
C3—Fe1—C868.92 (18)C8—C5—C3108.7 (4)
C3—Fe1—C1168.98 (17)C8—C5—H5125.6
C3—Fe1—C24129.2 (2)Fe1—C6—H6126.5
C3—Fe1—C25108.7 (2)C3—C6—Fe168.2 (2)
C3—Fe1—C27167.1 (2)C3—C6—H6126.2
C3—Fe1—C28151.3 (3)C11—C6—Fe170.6 (3)
C5—Fe1—C341.46 (18)C11—C6—C3107.5 (4)
C5—Fe1—C669.37 (18)C11—C6—H6126.2
C5—Fe1—C840.50 (19)C1—C7—H7118.3
C5—Fe1—C1168.30 (19)C12—C7—C1123.4 (4)
C5—Fe1—C24166.2 (2)C12—C7—H7118.3
C5—Fe1—C25128.1 (2)Fe1—C8—H8127.2
C5—Fe1—C26106.1 (2)C5—C8—Fe168.2 (2)
C5—Fe1—C27150.9 (2)C5—C8—H8125.8
C5—Fe1—C28116.8 (2)C5—C8—C11108.4 (4)
C6—Fe1—C868.35 (19)C11—C8—Fe170.4 (3)
C6—Fe1—C1140.50 (18)C11—C8—H8125.8
C8—Fe1—C1140.20 (19)Fe2—C9—H9125.2
C24—Fe1—C6110.3 (2)C20—C9—Fe270.3 (3)
C24—Fe1—C8153.1 (2)C20—C9—H9125.7
C24—Fe1—C11121.0 (2)C21—C9—Fe270.4 (3)
C25—Fe1—C6120.4 (2)C21—C9—H9125.7
C25—Fe1—C8165.0 (3)C21—C9—C20108.6 (4)
C25—Fe1—C11154.1 (2)F6—C10—F4106.0 (4)
C25—Fe1—C2439.4 (3)F6—C10—F5107.2 (4)
C25—Fe1—C2766.7 (2)F6—C10—C12112.6 (4)
C26—Fe1—C3117.4 (2)F4—C10—C12110.2 (4)
C26—Fe1—C6153.2 (3)F5—C10—F4105.5 (4)
C26—Fe1—C8126.1 (2)F5—C10—C12114.9 (4)
C26—Fe1—C11164.1 (3)Fe1—C11—H11127.5
C26—Fe1—C2467.6 (2)C6—C11—Fe168.9 (2)
C26—Fe1—C2540.7 (3)C6—C11—H11125.8
C26—Fe1—C2767.6 (3)C8—C11—Fe169.4 (3)
C26—Fe1—C2840.8 (3)C8—C11—C6108.3 (4)
C27—Fe1—C6129.1 (2)C8—C11—H11125.8
C27—Fe1—C8118.8 (2)O4—C12—C7130.3 (4)
C27—Fe1—C11109.6 (2)O4—C12—C10112.4 (4)
C27—Fe1—C2439.7 (2)C7—C12—C10117.3 (4)
C28—Fe1—C6165.2 (3)F1—C13—F3106.3 (4)
C28—Fe1—C8106.9 (2)F1—C13—C2111.4 (4)
C28—Fe1—C11127.1 (2)F3—C13—C2113.7 (4)
C28—Fe1—C2467.2 (2)F2—C13—F1106.9 (4)
C28—Fe1—C2567.7 (2)F2—C13—F3107.2 (4)
C28—Fe1—C2739.8 (3)F2—C13—C2110.9 (4)
O4—Co1—O388.20 (12)Fe2—C14—H14126.8
O4—Co1—O684.49 (12)C17—C14—Fe269.1 (3)
O4—Co1—O299.68 (12)C17—C14—H14125.9
O4—Co1—O591.75 (12)C17—C14—C23108.1 (4)
O3—Co1—O693.19 (11)C23—C14—Fe269.7 (3)
O3—Co1—O5177.31 (12)C23—C14—H14125.9
O2—Co1—O392.11 (12)C4—C15—Fe2120.1 (3)
O2—Co1—O6173.36 (12)C16—C15—Fe269.8 (3)
O2—Co1—O585.25 (12)C16—C15—C4124.5 (4)
O1—Co1—O4170.17 (12)C17—C15—Fe269.5 (3)
O1—Co1—O393.61 (12)C17—C15—C4128.0 (4)
O1—Co1—O685.76 (12)C17—C15—C16107.1 (4)
O1—Co1—O289.91 (12)Fe2—C16—H16126.4
O1—Co1—O586.89 (13)C15—C16—Fe268.8 (2)
O5—Co1—O689.48 (12)C15—C16—H16126.0
C9—Fe2—C14161.3 (2)C23—C16—Fe270.3 (3)
C9—Fe2—C16121.12 (19)C23—C16—C15108.0 (4)
C9—Fe2—C1968.09 (19)C23—C16—H16126.0
C9—Fe2—C2040.3 (2)Fe2—C17—H17126.0
C9—Fe2—C2140.1 (2)C14—C17—Fe270.6 (3)
C9—Fe2—C2267.8 (2)C14—C17—C15108.6 (4)
C9—Fe2—C23156.4 (2)C14—C17—H17125.7
C14—Fe2—C22122.4 (2)C15—C17—Fe269.2 (3)
C14—Fe2—C2340.7 (2)C15—C17—H17125.7
C15—Fe2—C9106.95 (19)C2—C18—C4124.5 (4)
C15—Fe2—C1468.69 (18)C2—C18—H18117.7
C15—Fe2—C1641.35 (18)C4—C18—H18117.7
C15—Fe2—C1741.26 (18)Fe2—C19—H19125.5
C15—Fe2—C19157.4 (2)C20—C19—Fe269.7 (3)
C15—Fe2—C20121.1 (2)C20—C19—H19126.1
C15—Fe2—C21123.60 (19)C22—C19—Fe270.4 (3)
C15—Fe2—C22160.5 (2)C22—C19—H19126.1
C15—Fe2—C2368.74 (19)C22—C19—C20107.8 (4)
C16—Fe2—C1468.40 (19)Fe2—C20—H20126.4
C16—Fe2—C19160.3 (2)C9—C20—Fe269.5 (3)
C16—Fe2—C20156.71 (19)C9—C20—C19107.5 (5)
C16—Fe2—C21107.2 (2)C9—C20—H20126.3
C16—Fe2—C22123.9 (2)C19—C20—Fe269.5 (3)
C16—Fe2—C2340.34 (18)C19—C20—H20126.3
C17—Fe2—C9124.7 (2)Fe2—C21—H21126.1
C17—Fe2—C1440.23 (19)C9—C21—Fe269.5 (3)
C17—Fe2—C1669.0 (2)C9—C21—H21125.9
C17—Fe2—C19122.1 (2)C9—C21—C22108.1 (5)
C17—Fe2—C20108.1 (2)C22—C21—Fe270.1 (3)
C17—Fe2—C21160.95 (19)C22—C21—H21125.9
C17—Fe2—C22157.2 (2)Fe2—C22—H22126.4
C17—Fe2—C2368.3 (2)C19—C22—Fe269.5 (3)
C19—Fe2—C14108.5 (2)C19—C22—C21107.9 (5)
C19—Fe2—C2040.9 (2)C19—C22—H22126.0
C19—Fe2—C2167.7 (2)C21—C22—Fe269.6 (3)
C19—Fe2—C2240.1 (2)C21—C22—H22126.0
C19—Fe2—C23124.7 (2)Fe2—C23—H23126.7
C20—Fe2—C14125.2 (2)C14—C23—Fe269.6 (3)
C20—Fe2—C2167.6 (2)C14—C23—H23125.9
C20—Fe2—C2267.9 (2)C16—C23—Fe269.4 (3)
C20—Fe2—C23161.9 (2)C16—C23—C14108.2 (4)
C21—Fe2—C14157.4 (2)C16—C23—H23125.9
C21—Fe2—C2240.35 (19)Fe1—C24—H24125.4
C21—Fe2—C23121.6 (2)C25—C24—Fe170.3 (3)
C23—Fe2—C22108.1 (2)C25—C24—H24125.7
C12—O4—Co1124.6 (3)C25—C24—C27108.5 (5)
C1—O3—Co1127.0 (3)C27—C24—Fe170.1 (3)
Co1—O6—H6A118 (4)C27—C24—H24125.7
Co1—O6—H6B114 (4)Fe1—C25—H25126.3
H6A—O6—H6B108 (5)C24—C25—Fe170.4 (3)
C4—O2—Co1123.8 (3)C24—C25—H25125.8
C2—O1—Co1120.9 (3)C24—C25—C26108.4 (5)
Co1—O5—H5A119 (4)C26—C25—Fe169.1 (3)
Co1—O5—H5B116 (4)C26—C25—H25125.8
H5A—O5—H5B103 (6)Fe1—C26—H26124.9
O3—C1—C3118.7 (4)C25—C26—Fe170.2 (3)
O3—C1—C7123.3 (4)C25—C26—H26126.7
C7—C1—C3118.0 (4)C28—C26—Fe169.8 (3)
O1—C2—C13112.7 (4)C28—C26—C25106.6 (6)
O1—C2—C18129.0 (4)C28—C26—H26126.7
C18—C2—C13118.2 (4)Fe1—C27—H27126.0
C1—C3—Fe1118.9 (3)C24—C27—Fe170.1 (3)
C5—C3—Fe169.1 (2)C24—C27—H27125.7
C5—C3—C1128.0 (4)C28—C27—Fe169.8 (3)
C5—C3—C6107.0 (4)C28—C27—C24108.7 (6)
C6—C3—Fe170.1 (2)C28—C27—H27125.7
C6—C3—C1124.4 (4)Fe1—C28—H28125.7
O2—C4—C15117.4 (4)C26—C28—Fe169.4 (3)
O2—C4—C18125.1 (4)C26—C28—H28126.1
C18—C4—C15117.5 (4)C27—C28—Fe170.4 (3)
Fe1—C5—H5125.2C27—C28—C26107.8 (5)
C3—C5—Fe169.4 (2)C27—C28—H28126.1
C3—C5—H5125.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O6i0.89 (4)1.97 (4)2.797 (5)154 (6)
O5—H5B···O4i0.88 (4)2.01 (4)2.781 (4)146 (5)
O6—H6A···O3ii0.88 (4)1.91 (5)2.739 (5)156 (4)
O6—H6B···O1ii0.89 (6)1.99 (6)2.741 (5)141 (5)
C25—H25···O20.932.573.467 (7)163
C28—H28···F3iii0.932.553.449 (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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