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

Journal logoIUCrDATA
ISSN: 2414-3146

4,5-Diferrocenyl-1,2-di­thiol-3-one

CROSSMARK_Color_square_no_text.svg

aFacultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Ciudad de México, 04510, Mexico
*Correspondence e-mail: eiklimova@yahoo.com.mx

Edited by M. Weil, Vienna University of Technology, Austria (Received 10 March 2018; accepted 3 May 2018; online 18 May 2018)

The title compound, [Fe2(C5H5)2(C13H8OS2)], crystallizes with two mol­ecules in the asymmetric unit. Each mol­ecule comprises a pair of ferrocenyl units bridged by a di­thiol-3-one moiety. The dihedral angles between the di­thiol-3-one ring and the substituted cyclo­penta­dienyl rings are in the range 32.4 (3)–39.3 (3)°. One of the di­thiol-3-one rings was refined as being disordered over two sets of sites while the same kind of disorder in the other mol­ecule was negligible. The molecular packing is dominated by C—H⋯O hydrogen bonds and C—H⋯π inter­actions.

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

Structure description

Background to the chemistry of ferrocenes and their potential applications was compiled by Togni & Hayashi (1995[Togni, A. & Hayashi, T. (1995). Ferrocenes. Weinheim: VCH]). 1,2-Di­thiole-3-one derivatives are of current inter­est since they have a broad spectrum of biological activities (He et al., 2004[He, X., Reeve, A. M. E., Desai, U. R., Kellogg, G. E. & Reynolds, K. A. (2004). Antimicrob. Agents Chemother. 48, 3093-3102.]) and may be useful synthons for many sulfur-containing heterocycles (Konstanti­nova et al., 2007[Konstantinova, L. S., Berezin, A. A., Lysov, K. A. & Rakitin, O. A. (2007). Tetrahedron Lett. 48, 5851-5854.]). An analogue of these compounds is Oltipraz (4-methyl-5-(2-pyrazin­yl)-1,2-di­thiole-3-thione) that has been clinically tested as a preventive agent against various types of cancer (Iida et al., 2004[Iida, K., Itoh, K., Kumagai, Y., Oyasu, R., Hattori, K., Kawai, K., Shimazui, T., Akaza, H. & Yamamoto, M. (2004). Cancer Res. 64, 6424-6431.]).

Each of the two mol­ecules A and B in the asymmetric unit of the title compound is constituted by a pair of ferrocenyl units bridged by a di­thiol-3-one ring (Fig. 1[link]). The cyclo­penta­dienyl (Cp) rings are almost parallel, making dihedral angles of 1.3 (3) and 1.7 (2)° for mol­ecule A containing Fe1 and Fe2, and 1.7 (2) and 2.7 (3)° for mol­ecule B containing Fe3 and Fe4, respectively. The dihedral angles between the di­thiol-3-one ring and the substituted cyclo­penta­dienyl rings are 39.3 (3) and 32.6 (2)° for mol­ecule A and 37.6 (2) and 32.4 (2)° for mol­ecule B. The cyclo­penta­dienyl rings of the ferrocenyl moieties in both mol­ecules adopt eclipsed conformations. All bond lengths and angles for two crystallographically independent mol­ecules are similar (Table 1[link]).

Table 1
Selected geometric parameters (Å, °)

C5—C6 1.474 (5) C29—C30 1.466 (5)
C5—Fe1 2.048 (4) C29—Fe3 2.052 (4)
C6—C7 1.357 (6) C30—C31 1.361 (5)
C7—C8 1.465 (5) C31—C33 1.471 (5)
C7—S1 1.756 (5) C31—S4 1.748 (4)
C8—Fe2 2.055 (4) C33—Fe4 2.037 (4)
S2—S1 1.983 (6) S4—S5 2.0259 (15)
C18—O1 1.25 (3) C32—O3 1.182 (5)
       
C4—C5—C6—C7 37.8 (6) C25—C29—C30—C31 144.0 (4)
C6—C7—C8—C9 33.9 (6) C30—C31—C33—C34 147.4 (4)
[Figure 1]
Figure 1
The mol­ecular structures of the two entities in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of disorder is shown for mol­ecule A.

In the crystal structure (Fig. 2[link]), mol­ecules B are linked via weak C—H⋯O hydrogen bonds between the Cp rings and the O atoms of the 1,2-di­thiole-3-one moieties (Table 2[link]) with a graph-set motif C11(8) forming a chain parallel to the a axis. Mol­ecules A and B, on the other hand, show inter­molecular inter­actions of the type C—H⋯π, with C1—H1⋯Cg10 and C43—H43⋯Cg6 distances of 3.04 and 3.12 Å, respectively, where Cg10 and Cg6 are the centroids of the rings C38–C42 and C20–24. These inter­actions form slabs lying parallel to the ac plane.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C36S—H36⋯O3i 1.00 2.36 3.354 (6) 170
Symmetry code: (i) x+1, y, z.
[Figure 2]
Figure 2
The molecular packing of the title compound showing inter­molecular contacts of the type C—H⋯O forming graph set motifs C11(8) along the a axis, as well as C—H⋯π inter­actions parallel to the ac plane. Mol­ecule A is green, mol­ecule B is blue.

Synthesis and crystallization

A mixture of sodium sulfide (10 mmol) and sulfur (5 mmol) in ethanol (80 ml) was added to 1,2-diferrocenyl­cyclo­propenone (5 mmol) and stirred at 353 K for 4 h. The solvents were removed in vacuo, and the residues purified by column chromatography with alumina and a mixture of hexa­ne:diethyl ether (ratio 1:1 v/v) as eluent. Red crystals of 4,5-diferrocenyl-1,2-di­thiol-3-one, suitable for single-crystal diffraction analysis, were obtained by slow evaporation of a saturated di­chloro­methane/hexane (ratio 1:1 v/v) solution. Yield (75%), mp. 468-470 K.

1H NMR (300 MHz, CDCl3) δ: 4.24 (5 H, s, C5H5), δ: 4.05 (5 H, s, C5H5), δ: 4.04 (4 H, s, C5H4), δ: 4.22 (2 H, m, C5H4), δ: 4.17 (2 H, s, C5H4) p.p.m., 13C NMR (75 MHz, CDCl3) δ: 79.45, 81.45 (2Cipso Fc), δ: 69.60 (C5H5), δ: 70.61 (C5H5), δ: 4.60, 69.55, 69.03, 67.96 (4C5H4), 136.15, 164.69, (2 C), 169.25 (C=O) p.p.m., MS: m/z 486 [M]+. Analysis calculated for C23H18Fe2OS2: C, 56.90, H, 3.68, S, 12.85, Found C, 56.70, H, 3.90, S, 13.05%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. Atoms C18, O1 and S1 of mol­ecule A were refined as being disordered over two sets of sites with occupancies of 0.56: 0.44 using restraints so that the bond lengths and angles of the two components are comparable. Remaining electron densities close to the same type of atoms were also found for mol­ecule B but to a much lesser extend (preliminary refinement of the occupancies about 0.93:0.07). For the final model this type of disorder was neglected.

Table 3
Experimental details

Crystal data
Chemical formula [Fe2(C5H5)2(C13H8OS2)]
Mr 486.19
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 130
a, b, c (Å) 9.8525 (4), 10.6407 (6), 19.2720 (9)
α, β, γ (°) 98.867 (4), 95.255 (4), 105.512 (4)
V3) 1904.76 (17)
Z 4
Radiation type Mo Kα
μ (mm−1) 1.75
Crystal size (mm) 0.16 × 0.13 × 0.06
 
Data collection
Diffractometer Agilent Xcalibur Atlas Gemini
Absorption correction Analytical (CrysAlis RED; Agilent, 2013[Agilent (2013). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.])
Tmin, Tmax 0.856, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections 19834, 7772, 5624
Rint 0.045
(sin θ/λ)max−1) 0.625
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.110, 1.02
No. of reflections 7772
No. of parameters 515
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.91, −0.51
Computer programs: CrysAlis PRO and CrysAlis RED (Agilent, 2013[Agilent (2013). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: ?; data reduction: CrysAlis RED (Agilent, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008).

4,5-Diferrocenyl-1,2-dithiol-3-one top
Crystal data top
[Fe2(C5H5)2(C13H8OS2)]Z = 4
Mr = 486.19F(000) = 992
Triclinic, P1Dx = 1.695 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8525 (4) ÅCell parameters from 4380 reflections
b = 10.6407 (6) Åθ = 3.5–29.5°
c = 19.2720 (9) ŵ = 1.75 mm1
α = 98.867 (4)°T = 130 K
β = 95.255 (4)°Block, dark red
γ = 105.512 (4)°0.16 × 0.13 × 0.06 mm
V = 1904.76 (17) Å3
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer
7772 independent reflections
Graphite monochromator5624 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1Rint = 0.045
ω scansθmax = 26.4°, θmin = 3.5°
Absorption correction: analytical
(CrysAlis RED; Agilent, 2013)
h = 1212
Tmin = 0.856, Tmax = 0.937k = 1313
19834 measured reflectionsl = 2424
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0398P)2 + 2.1419P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7772 reflectionsΔρmax = 0.91 e Å3
515 parametersΔρmin = 0.51 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.7650 (4)0.2765 (4)0.8413 (2)0.0277 (9)
H10.7177660.3617550.8075030.033*
C20.9125 (4)0.2109 (4)0.8546 (2)0.0283 (9)
H20.9878120.2427260.832180.034*
C30.9362 (4)0.0949 (4)0.9059 (2)0.0264 (9)
H31.0309540.0304830.9258190.032*
C40.8038 (4)0.0858 (4)0.9250 (2)0.0252 (9)
H40.7881020.0135830.9604290.03*
C50.6954 (4)0.1981 (4)0.8841 (2)0.0246 (9)
C60.5408 (4)0.2258 (4)0.8849 (2)0.0259 (9)
C70.4686 (4)0.1333 (4)0.8899 (2)0.0248 (9)
C80.5258 (4)0.0088 (4)0.8901 (2)0.0242 (9)
C90.6355 (4)0.0713 (4)0.8529 (2)0.0241 (9)
H90.6888040.0244830.8213150.029*
C100.6565 (4)0.2088 (4)0.8676 (2)0.0294 (9)
H100.7273510.2767380.8486410.035*
C110.5580 (4)0.2346 (4)0.9140 (2)0.0334 (10)
H110.5476660.3238620.9331310.04*
C120.4767 (4)0.1116 (4)0.9277 (2)0.0263 (9)
H120.3991140.0987590.9582040.032*
C130.2404 (4)0.0579 (5)0.7823 (2)0.0341 (10)
H130.1598340.0198290.8079370.041*
C140.3016 (5)0.1943 (5)0.7819 (2)0.0375 (11)
H140.2723460.2697190.8075270.045*
C150.4120 (5)0.2050 (5)0.7387 (2)0.0381 (11)
H150.4743380.2896120.7289650.046*
C160.4199 (5)0.0770 (5)0.7127 (2)0.0378 (11)
H160.4885980.0548510.6811390.045*
C170.3151 (4)0.0157 (5)0.7394 (2)0.0362 (11)
H170.2956950.1143550.7294350.043*
C200.8309 (6)0.2611 (5)1.0507 (2)0.0427 (12)
H200.8085910.1924041.0856890.051*
C210.9678 (5)0.2604 (5)1.0344 (3)0.0482 (14)
H211.0591390.191951.0558880.058*
C220.9523 (5)0.3730 (5)0.9829 (3)0.0500 (14)
H221.0311130.3992570.9608670.06*
C230.8068 (5)0.4429 (5)0.9671 (3)0.0432 (12)
H230.7642020.5278070.9323510.052*
C240.7318 (5)0.3733 (5)1.0099 (2)0.0400 (11)
H240.6267540.399541.0106820.048*
Fe10.83868 (6)0.25721 (6)0.94571 (3)0.02384 (14)
Fe20.45226 (6)0.11315 (6)0.82134 (3)0.02371 (14)
S20.26696 (11)0.37118 (12)0.89084 (6)0.0378 (3)
C180.449 (3)0.364 (2)0.8800 (13)0.037 (6)0.566 (9)
O10.4857 (6)0.4677 (9)0.8665 (4)0.0383 (17)0.566 (9)
S10.2859 (4)0.1795 (5)0.8963 (3)0.0314 (14)0.566 (9)
C18P0.316 (3)0.188 (3)0.8948 (15)0.037 (6)0.434 (9)
O1P0.2338 (10)0.1248 (10)0.9115 (5)0.046 (2)0.434 (9)
S1P0.4606 (8)0.3903 (8)0.8827 (5)0.033 (2)0.434 (9)
C250.0640 (4)0.4890 (4)0.6256 (2)0.0303 (10)
H250.001860.4397690.604920.036*
C260.1588 (4)0.4436 (4)0.6905 (2)0.0328 (10)
H260.1754210.3565390.7231450.039*
C270.2257 (4)0.5430 (4)0.7008 (2)0.0312 (10)
H270.2974640.538270.7420710.037*
C280.1719 (4)0.6507 (4)0.6437 (2)0.0277 (9)
H280.1993840.735270.6374660.033*
C290.0714 (4)0.6183 (4)0.5959 (2)0.0240 (9)
C300.0088 (4)0.7010 (4)0.52902 (18)0.0218 (5)
C310.0423 (4)0.7819 (4)0.48323 (18)0.0218 (5)
C320.1611 (4)0.6994 (4)0.51047 (19)0.0218 (5)
C330.1864 (4)0.7976 (4)0.4869 (2)0.0288 (9)
C340.2209 (4)0.9175 (5)0.4626 (2)0.0351 (11)
H340.1517231.0048980.4400250.042*
C350.3703 (5)0.8902 (6)0.4755 (3)0.0468 (14)
H350.42520.9552660.4632790.056*
C360.4291 (5)0.7560 (6)0.5073 (2)0.0517 (15)
H360.5328150.7097740.5217390.062*
C370.3161 (4)0.6955 (5)0.5143 (2)0.0418 (12)
H370.3258460.6009540.5351990.05*
C380.2421 (6)0.8212 (5)0.3059 (2)0.0507 (14)
H380.1654840.9022670.2812060.061*
C390.3910 (7)0.8058 (7)0.3170 (3)0.0611 (18)
H390.4382320.8760790.3025690.073*
C400.4575 (6)0.6801 (7)0.3507 (3)0.0631 (17)
H400.5624680.6432380.3657390.076*
C410.3600 (6)0.6110 (5)0.3620 (3)0.0523 (14)
H410.3815090.515990.3855770.063*
C420.2260 (5)0.6961 (5)0.3344 (2)0.0389 (11)
H420.1341590.6728520.3344690.047*
C430.0265 (4)0.6703 (5)0.7900 (2)0.0336 (10)
H430.047190.6585210.8316380.04*
C440.0753 (4)0.7821 (4)0.7351 (2)0.0347 (10)
H440.0415580.8632850.7308260.042*
C450.1783 (4)0.7603 (4)0.6870 (2)0.0354 (11)
H450.2311370.8229220.6427650.042*
C460.1940 (4)0.6329 (5)0.7123 (2)0.0352 (11)
H460.260210.5900690.6892520.042*
C470.1000 (4)0.5783 (4)0.7762 (2)0.0346 (10)
H470.0876760.4895490.8063510.041*
Fe30.01045 (5)0.61637 (5)0.69496 (3)0.02121 (14)
Fe40.31671 (6)0.77061 (6)0.41095 (3)0.02489 (15)
O30.2167 (3)0.6240 (4)0.53877 (17)0.0477 (9)
S40.07427 (11)0.88197 (12)0.40941 (6)0.0358 (3)
S50.24512 (10)0.81968 (11)0.43199 (6)0.0323 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.035 (2)0.028 (2)0.020 (2)0.0103 (18)0.0017 (17)0.0019 (17)
C20.029 (2)0.037 (3)0.022 (2)0.0097 (18)0.0093 (17)0.0097 (19)
C30.0230 (19)0.031 (2)0.026 (2)0.0046 (16)0.0021 (17)0.0138 (18)
C40.028 (2)0.023 (2)0.026 (2)0.0112 (16)0.0008 (17)0.0059 (17)
C50.027 (2)0.030 (2)0.0192 (19)0.0106 (17)0.0003 (16)0.0079 (17)
C60.028 (2)0.028 (2)0.021 (2)0.0068 (17)0.0011 (17)0.0052 (17)
C70.0229 (19)0.030 (2)0.020 (2)0.0038 (16)0.0029 (16)0.0071 (17)
C80.0201 (18)0.032 (2)0.020 (2)0.0088 (16)0.0035 (16)0.0035 (17)
C90.0223 (19)0.030 (2)0.021 (2)0.0123 (16)0.0005 (16)0.0030 (17)
C100.0201 (19)0.030 (2)0.035 (2)0.0054 (16)0.0003 (18)0.0041 (19)
C110.030 (2)0.033 (3)0.031 (2)0.0089 (18)0.0028 (19)0.0066 (19)
C120.0240 (19)0.034 (2)0.018 (2)0.0077 (17)0.0001 (16)0.0011 (17)
C130.024 (2)0.054 (3)0.025 (2)0.0128 (19)0.0040 (18)0.012 (2)
C140.041 (2)0.052 (3)0.035 (2)0.031 (2)0.008 (2)0.023 (2)
C150.043 (3)0.049 (3)0.032 (2)0.019 (2)0.008 (2)0.023 (2)
C160.041 (2)0.058 (3)0.020 (2)0.022 (2)0.0011 (19)0.012 (2)
C170.039 (2)0.043 (3)0.023 (2)0.013 (2)0.0102 (19)0.002 (2)
C200.078 (4)0.044 (3)0.019 (2)0.034 (3)0.010 (2)0.015 (2)
C210.044 (3)0.050 (3)0.052 (3)0.010 (2)0.011 (2)0.032 (3)
C220.049 (3)0.060 (4)0.071 (4)0.039 (3)0.031 (3)0.046 (3)
C230.067 (3)0.023 (3)0.040 (3)0.010 (2)0.016 (2)0.009 (2)
C240.040 (3)0.050 (3)0.039 (3)0.018 (2)0.012 (2)0.023 (2)
Fe10.0270 (3)0.0243 (3)0.0221 (3)0.0099 (2)0.0033 (2)0.0056 (2)
Fe20.0247 (3)0.0275 (3)0.0217 (3)0.0112 (2)0.0033 (2)0.0059 (2)
S20.0268 (5)0.0408 (7)0.0401 (7)0.0004 (5)0.0029 (5)0.0091 (5)
C180.047 (9)0.049 (10)0.018 (5)0.025 (6)0.006 (5)0.002 (5)
O10.035 (3)0.023 (4)0.052 (4)0.005 (3)0.001 (3)0.002 (3)
S10.0215 (18)0.033 (2)0.0409 (17)0.0053 (15)0.0072 (14)0.0124 (14)
C18P0.047 (9)0.049 (10)0.018 (5)0.025 (6)0.006 (5)0.002 (5)
O1P0.031 (4)0.047 (6)0.069 (6)0.023 (4)0.011 (4)0.015 (5)
S1P0.024 (2)0.025 (3)0.044 (2)0.002 (2)0.0001 (17)0.004 (2)
C250.033 (2)0.035 (3)0.027 (2)0.0073 (18)0.0118 (18)0.0153 (19)
C260.034 (2)0.031 (2)0.025 (2)0.0053 (18)0.0078 (19)0.0041 (19)
C270.022 (2)0.046 (3)0.023 (2)0.0059 (18)0.0014 (17)0.008 (2)
C280.0223 (19)0.044 (3)0.021 (2)0.0147 (18)0.0094 (17)0.0064 (19)
C290.0193 (18)0.036 (2)0.0201 (19)0.0089 (16)0.0126 (16)0.0081 (18)
C300.0198 (11)0.0356 (14)0.0118 (10)0.0103 (9)0.0013 (9)0.0063 (9)
C310.0198 (11)0.0356 (14)0.0118 (10)0.0103 (9)0.0013 (9)0.0063 (9)
C320.0198 (11)0.0356 (14)0.0118 (10)0.0103 (9)0.0013 (9)0.0063 (9)
C330.023 (2)0.048 (3)0.018 (2)0.0121 (18)0.0062 (17)0.0104 (19)
C340.034 (2)0.048 (3)0.036 (2)0.018 (2)0.013 (2)0.027 (2)
C350.036 (3)0.088 (4)0.038 (3)0.036 (3)0.018 (2)0.037 (3)
C360.022 (2)0.113 (5)0.021 (2)0.023 (3)0.0027 (19)0.010 (3)
C370.024 (2)0.070 (4)0.024 (2)0.009 (2)0.0053 (18)0.007 (2)
C380.090 (4)0.036 (3)0.017 (2)0.003 (3)0.002 (2)0.007 (2)
C390.103 (5)0.086 (5)0.038 (3)0.078 (4)0.043 (3)0.033 (3)
C400.049 (3)0.094 (5)0.065 (4)0.026 (3)0.033 (3)0.050 (4)
C410.066 (3)0.033 (3)0.061 (4)0.013 (3)0.003 (3)0.019 (3)
C420.045 (3)0.062 (3)0.025 (2)0.032 (2)0.013 (2)0.018 (2)
C430.031 (2)0.050 (3)0.023 (2)0.007 (2)0.0134 (18)0.018 (2)
C440.035 (2)0.028 (2)0.048 (3)0.0095 (19)0.017 (2)0.019 (2)
C450.030 (2)0.038 (3)0.031 (2)0.0026 (19)0.0128 (19)0.003 (2)
C460.025 (2)0.052 (3)0.042 (3)0.018 (2)0.020 (2)0.026 (2)
C470.037 (2)0.033 (3)0.035 (2)0.0073 (19)0.020 (2)0.004 (2)
Fe30.0230 (3)0.0241 (3)0.0175 (3)0.0067 (2)0.0058 (2)0.0050 (2)
Fe40.0263 (3)0.0316 (3)0.0211 (3)0.0128 (2)0.0091 (2)0.0063 (3)
O30.0367 (17)0.066 (2)0.0414 (19)0.0227 (16)0.0037 (15)0.0030 (17)
S40.0283 (5)0.0486 (7)0.0276 (6)0.0101 (5)0.0025 (5)0.0011 (5)
S50.0214 (5)0.0456 (7)0.0278 (6)0.0062 (4)0.0025 (4)0.0104 (5)
Geometric parameters (Å, º) top
C1—C21.414 (6)C18—O11.25 (3)
C1—C51.430 (5)C18P—O1P1.22 (3)
C1—Fe12.036 (4)C25—C261.425 (6)
C1—H11C25—C291.430 (6)
C2—C31.408 (6)C25—Fe32.050 (4)
C2—Fe12.041 (4)C25—H251
C2—H21C26—C271.416 (6)
C3—C41.412 (5)C26—Fe32.039 (4)
C3—Fe12.037 (4)C26—H261
C3—H31C27—C281.409 (6)
C4—C51.436 (5)C27—Fe32.041 (4)
C4—Fe12.035 (4)C27—H271
C4—H41C28—C291.436 (5)
C5—C61.474 (5)C28—Fe32.031 (4)
C5—Fe12.048 (4)C28—H281
C6—C71.357 (6)C29—C301.466 (5)
C6—C181.49 (2)C29—Fe32.052 (4)
C6—S1P1.708 (8)C30—C311.361 (5)
C7—C81.465 (5)C30—C321.516 (5)
C7—C18P1.48 (2)C31—C331.471 (5)
C7—S11.756 (5)C31—S41.748 (4)
C8—C91.425 (5)C32—O31.182 (5)
C8—C121.434 (5)C32—S51.794 (4)
C8—Fe22.055 (4)C33—C341.428 (6)
C9—C101.401 (6)C33—C371.431 (6)
C9—Fe22.034 (4)C33—Fe42.037 (4)
C9—H91C34—C351.413 (6)
C10—C111.430 (6)C34—Fe42.046 (4)
C10—Fe22.044 (4)C34—H341
C10—H101C35—C361.405 (8)
C11—C121.417 (6)C35—Fe42.043 (4)
C11—Fe22.042 (4)C35—H351
C11—H111C36—C371.434 (7)
C12—Fe22.044 (4)C36—Fe42.036 (4)
C12—H121C36—H361
C13—C141.416 (6)C37—Fe42.029 (4)
C13—C171.435 (6)C37—H371
C13—Fe22.047 (4)C38—C421.415 (7)
C13—H131C38—C391.424 (8)
C14—C151.420 (6)C38—Fe42.026 (4)
C14—Fe22.051 (4)C38—H381
C14—H141C39—C401.350 (8)
C15—C161.402 (6)C39—Fe42.033 (5)
C15—Fe22.055 (4)C39—H391
C15—H151C40—C411.371 (8)
C16—C171.419 (6)C40—Fe42.031 (5)
C16—Fe22.049 (4)C40—H401
C16—H161C41—C421.388 (7)
C17—Fe22.037 (4)C41—Fe42.033 (5)
C17—H171C41—H411
C20—C241.394 (7)C42—Fe42.025 (4)
C20—C211.410 (7)C42—H421
C20—Fe12.037 (4)C43—C471.406 (6)
C20—H201C43—C441.407 (6)
C21—C221.398 (7)C43—Fe32.037 (4)
C21—Fe12.045 (4)C43—H431
C21—H211C44—C451.401 (6)
C22—C231.408 (7)C44—Fe32.041 (4)
C22—Fe12.036 (4)C44—H441
C22—H221C45—C461.421 (6)
C23—C241.410 (6)C45—Fe32.044 (4)
C23—Fe12.029 (4)C45—H451
C23—H231C46—C471.412 (6)
C24—Fe12.044 (4)C46—Fe32.038 (4)
C24—H241C46—H461
S2—C181.80 (3)C47—Fe32.038 (4)
S2—C18P1.87 (3)C47—H471
S2—S11.983 (6)S4—S52.0259 (15)
S2—S1P1.989 (9)
C2—C1—C5107.7 (4)O1P—C18P—C7127 (3)
C2—C1—Fe169.9 (2)O1P—C18P—S2120.9 (19)
C5—C1—Fe169.9 (2)C7—C18P—S2111.5 (16)
C2—C1—H1126.2C6—S1P—S295.8 (5)
C5—C1—H1126.2C26—C25—C29108.1 (4)
Fe1—C1—H1126.2C26—C25—Fe369.2 (2)
C3—C2—C1108.7 (4)C29—C25—Fe369.7 (2)
C3—C2—Fe169.7 (2)C26—C25—H25126
C1—C2—Fe169.5 (2)C29—C25—H25126
C3—C2—H2125.6Fe3—C25—H25126
C1—C2—H2125.6C27—C26—C25108.1 (4)
Fe1—C2—H2125.6C27—C26—Fe369.7 (2)
C2—C3—C4108.5 (3)C25—C26—Fe370.0 (2)
C2—C3—Fe170.0 (2)C27—C26—H26125.9
C4—C3—Fe169.6 (2)C25—C26—H26125.9
C2—C3—H3125.8Fe3—C26—H26125.9
C4—C3—H3125.8C28—C27—C26108.4 (4)
Fe1—C3—H3125.8C28—C27—Fe369.4 (2)
C3—C4—C5107.7 (4)C26—C27—Fe369.6 (2)
C3—C4—Fe169.8 (2)C28—C27—H27125.8
C5—C4—Fe169.9 (2)C26—C27—H27125.8
C3—C4—H4126.1Fe3—C27—H27125.8
C5—C4—H4126.1C27—C28—C29108.5 (4)
Fe1—C4—H4126.1C27—C28—Fe370.1 (2)
C1—C5—C4107.4 (3)C29—C28—Fe370.2 (2)
C1—C5—C6126.3 (4)C27—C28—H28125.8
C4—C5—C6126.3 (4)C29—C28—H28125.8
C1—C5—Fe169.1 (2)Fe3—C28—H28125.8
C4—C5—Fe168.9 (2)C25—C29—C28107.0 (3)
C6—C5—Fe1128.4 (3)C25—C29—C30126.0 (3)
C7—C6—C5125.3 (4)C28—C29—C30127.0 (4)
C7—C6—C18113.7 (11)C25—C29—Fe369.5 (2)
C5—C6—C18121.0 (11)C28—C29—Fe368.6 (2)
C7—C6—S1P122.7 (4)C30—C29—Fe3127.0 (3)
C5—C6—S1P111.9 (4)C31—C30—C29124.8 (3)
C6—C7—C8127.1 (3)C31—C30—C32117.5 (3)
C6—C7—C18P113.6 (13)C29—C30—C32117.7 (3)
C8—C7—C18P119.2 (13)C30—C31—C33128.4 (3)
C6—C7—S1120.3 (4)C30—C31—S4117.9 (3)
C8—C7—S1112.6 (3)C33—C31—S4113.7 (3)
C9—C8—C12107.1 (3)O3—C32—C30126.5 (4)
C9—C8—C7127.7 (4)O3—C32—S5122.8 (3)
C12—C8—C7125.1 (3)C30—C32—S5110.5 (3)
C9—C8—Fe268.8 (2)C34—C33—C37108.3 (4)
C12—C8—Fe269.1 (2)C34—C33—C31125.6 (4)
C7—C8—Fe2125.9 (3)C37—C33—C31126.1 (4)
C10—C9—C8109.1 (4)C34—C33—Fe469.9 (2)
C10—C9—Fe270.3 (2)C37—C33—Fe469.1 (2)
C8—C9—Fe270.4 (2)C31—C33—Fe4126.0 (3)
C10—C9—H9125.5C35—C34—C33107.7 (4)
C8—C9—H9125.5C35—C34—Fe469.7 (3)
Fe2—C9—H9125.5C33—C34—Fe469.2 (2)
C9—C10—C11107.8 (4)C35—C34—H34126.1
C9—C10—Fe269.5 (2)C33—C34—H34126.1
C11—C10—Fe269.5 (2)Fe4—C34—H34126.1
C9—C10—H10126.1C36—C35—C34108.7 (4)
C11—C10—H10126.1C36—C35—Fe469.6 (3)
Fe2—C10—H10126.1C34—C35—Fe469.9 (2)
C12—C11—C10108.2 (4)C36—C35—H35125.7
C12—C11—Fe269.8 (2)C34—C35—H35125.7
C10—C11—Fe269.6 (2)Fe4—C35—H35125.7
C12—C11—H11125.9C35—C36—C37108.7 (4)
C10—C11—H11125.9C35—C36—Fe470.1 (3)
Fe2—C11—H11125.9C37—C36—Fe469.1 (2)
C11—C12—C8107.8 (3)C35—C36—H36125.6
C11—C12—Fe269.6 (2)C37—C36—H36125.6
C8—C12—Fe269.9 (2)Fe4—C36—H36125.6
C11—C12—H12126.1C33—C37—C36106.6 (5)
C8—C12—H12126.1C33—C37—Fe469.7 (2)
Fe2—C12—H12126.1C36—C37—Fe469.6 (3)
C14—C13—C17107.6 (4)C33—C37—H37126.7
C14—C13—Fe269.9 (2)C36—C37—H37126.7
C17—C13—Fe269.1 (2)Fe4—C37—H37126.7
C14—C13—H13126.2C42—C38—C39105.5 (5)
C17—C13—H13126.2C42—C38—Fe469.5 (2)
Fe2—C13—H13126.2C39—C38—Fe469.7 (3)
C13—C14—C15108.0 (4)C42—C38—H38127.2
C13—C14—Fe269.6 (2)C39—C38—H38127.2
C15—C14—Fe269.9 (2)Fe4—C38—H38127.2
C13—C14—H14126C40—C39—C38108.4 (5)
C15—C14—H14126C40—C39—Fe470.5 (3)
Fe2—C14—H14126C38—C39—Fe469.2 (3)
C16—C15—C14108.4 (4)C40—C39—H39125.8
C16—C15—Fe269.8 (2)C38—C39—H39125.8
C14—C15—Fe269.6 (2)Fe4—C39—H39125.8
C16—C15—H15125.8C39—C40—C41110.0 (5)
C14—C15—H15125.8C39—C40—Fe470.7 (3)
Fe2—C15—H15125.8C41—C40—Fe470.4 (3)
C15—C16—C17108.5 (4)C39—C40—H40125
C15—C16—Fe270.2 (2)C41—C40—H40125
C17—C16—Fe269.2 (2)Fe4—C40—H40125
C15—C16—H16125.8C40—C41—C42107.9 (5)
C17—C16—H16125.8C40—C41—Fe470.2 (3)
Fe2—C16—H16125.8C42—C41—Fe469.7 (3)
C16—C17—C13107.5 (4)C40—C41—H41126.1
C16—C17—Fe270.1 (2)C42—C41—H41126.1
C13—C17—Fe269.8 (2)Fe4—C41—H41126.1
C16—C17—H17126.2C41—C42—C38108.1 (4)
C13—C17—H17126.2C41—C42—Fe470.3 (3)
Fe2—C17—H17126.2C38—C42—Fe469.6 (2)
C24—C20—C21108.8 (4)C41—C42—H42125.9
C24—C20—Fe170.3 (3)C38—C42—H42125.9
C21—C20—Fe170.1 (3)Fe4—C42—H42125.9
C24—C20—H20125.6C47—C43—C44108.0 (4)
C21—C20—H20125.6C47—C43—Fe369.8 (2)
Fe1—C20—H20125.6C44—C43—Fe369.9 (2)
C22—C21—C20107.4 (4)C47—C43—H43126
C22—C21—Fe169.6 (3)C44—C43—H43126
C20—C21—Fe169.5 (2)Fe3—C43—H43126
C22—C21—H21126.3C45—C44—C43108.6 (4)
C20—C21—H21126.3C45—C44—Fe370.1 (2)
Fe1—C21—H21126.3C43—C44—Fe369.7 (2)
C21—C22—C23108.3 (4)C45—C44—H44125.7
C21—C22—Fe170.3 (3)C43—C44—H44125.7
C23—C22—Fe169.4 (3)Fe3—C44—H44125.7
C21—C22—H22125.9C44—C45—C46107.7 (4)
C23—C22—H22125.9C44—C45—Fe369.8 (2)
Fe1—C22—H22125.9C46—C45—Fe369.4 (2)
C22—C23—C24107.9 (5)C44—C45—H45126.1
C22—C23—Fe170.0 (3)C46—C45—H45126.1
C24—C23—Fe170.3 (3)Fe3—C45—H45126.1
C22—C23—H23126C47—C46—C45107.7 (4)
C24—C23—H23126C47—C46—Fe369.8 (2)
Fe1—C23—H23126C45—C46—Fe369.9 (2)
C20—C24—C23107.5 (4)C47—C46—H46126.2
C20—C24—Fe169.8 (3)C45—C46—H46126.2
C23—C24—Fe169.2 (3)Fe3—C46—H46126.2
C20—C24—H24126.2C43—C47—C46108.1 (4)
C23—C24—H24126.2C43—C47—Fe369.8 (2)
Fe1—C24—H24126.2C46—C47—Fe369.7 (2)
C23—Fe1—C4161.96 (18)C43—C47—H47126
C23—Fe1—C1107.29 (18)C46—C47—H47126
C4—Fe1—C169.13 (16)Fe3—C47—H47126
C23—Fe1—C2240.5 (2)C28—Fe3—C43122.97 (17)
C4—Fe1—C22156.2 (2)C28—Fe3—C46157.75 (18)
C1—Fe1—C22123.4 (2)C43—Fe3—C4668.09 (17)
C23—Fe1—C3156.13 (18)C28—Fe3—C47159.62 (17)
C4—Fe1—C340.58 (15)C43—Fe3—C4740.37 (17)
C1—Fe1—C368.53 (16)C46—Fe3—C4740.55 (17)
C22—Fe1—C3120.75 (18)C28—Fe3—C2668.51 (18)
C23—Fe1—C2067.58 (19)C43—Fe3—C26120.59 (18)
C4—Fe1—C20108.75 (18)C46—Fe3—C26125.21 (19)
C1—Fe1—C20158.06 (19)C47—Fe3—C26107.64 (18)
C22—Fe1—C2067.5 (2)C28—Fe3—C2740.49 (16)
C3—Fe1—C20124.96 (19)C43—Fe3—C27106.40 (16)
C23—Fe1—C2121.21 (18)C46—Fe3—C27161.05 (19)
C4—Fe1—C268.31 (17)C47—Fe3—C27123.67 (18)
C1—Fe1—C240.58 (16)C26—Fe3—C2740.63 (17)
C22—Fe1—C2106.97 (18)C28—Fe3—C44106.95 (18)
C3—Fe1—C240.39 (16)C43—Fe3—C4440.37 (18)
C20—Fe1—C2160.6 (2)C46—Fe3—C4467.93 (17)
C23—Fe1—C2440.51 (18)C47—Fe3—C4467.83 (18)
C4—Fe1—C24125.38 (17)C26—Fe3—C44155.64 (18)
C1—Fe1—C24122.32 (18)C27—Fe3—C44120.43 (17)
C22—Fe1—C2467.92 (18)C28—Fe3—C45121.42 (18)
C3—Fe1—C24161.50 (19)C43—Fe3—C4567.92 (17)
C20—Fe1—C2439.94 (19)C46—Fe3—C4540.75 (18)
C2—Fe1—C24157.27 (19)C47—Fe3—C4568.16 (17)
C23—Fe1—C2167.9 (2)C26—Fe3—C45162.63 (19)
C4—Fe1—C21121.7 (2)C27—Fe3—C45155.85 (19)
C1—Fe1—C21159.5 (2)C44—Fe3—C4540.10 (17)
C22—Fe1—C2140.1 (2)C28—Fe3—C2568.74 (17)
C3—Fe1—C21107.40 (17)C43—Fe3—C25156.72 (19)
C20—Fe1—C2140.42 (19)C46—Fe3—C25109.03 (17)
C2—Fe1—C21123.47 (18)C47—Fe3—C25122.29 (18)
C24—Fe1—C2167.80 (19)C26—Fe3—C2540.77 (16)
C23—Fe1—C5124.66 (19)C27—Fe3—C2568.43 (16)
C4—Fe1—C541.20 (15)C44—Fe3—C25161.95 (18)
C1—Fe1—C540.99 (15)C45—Fe3—C25126.01 (17)
C22—Fe1—C5160.8 (2)C28—Fe3—C2941.19 (15)
C3—Fe1—C568.55 (15)C43—Fe3—C29160.50 (18)
C20—Fe1—C5123.00 (18)C46—Fe3—C29122.54 (16)
C2—Fe1—C568.33 (16)C47—Fe3—C29157.92 (17)
C24—Fe1—C5108.79 (17)C26—Fe3—C2968.75 (16)
C21—Fe1—C5158.0 (2)C27—Fe3—C2968.67 (15)
C9—Fe2—C17117.78 (18)C44—Fe3—C29124.55 (18)
C9—Fe2—C1168.25 (17)C45—Fe3—C29108.41 (16)
C17—Fe2—C11169.18 (18)C25—Fe3—C2940.80 (16)
C9—Fe2—C1040.19 (16)C42—Fe4—C3840.90 (19)
C17—Fe2—C10149.26 (18)C42—Fe4—C37119.2 (2)
C11—Fe2—C1040.96 (16)C38—Fe4—C37155.9 (2)
C9—Fe2—C1268.65 (15)C42—Fe4—C4066.7 (2)
C17—Fe2—C12131.11 (17)C38—Fe4—C4067.4 (2)
C11—Fe2—C1240.59 (16)C37—Fe4—C40123.1 (3)
C10—Fe2—C1268.69 (16)C42—Fe4—C3967.71 (19)
C9—Fe2—C13152.24 (18)C38—Fe4—C3941.1 (2)
C17—Fe2—C1341.14 (17)C37—Fe4—C39159.4 (2)
C11—Fe2—C13129.68 (18)C40—Fe4—C3938.8 (2)
C10—Fe2—C13167.12 (18)C42—Fe4—C4140.0 (2)
C12—Fe2—C13109.75 (16)C38—Fe4—C4168.0 (2)
C9—Fe2—C16107.79 (17)C37—Fe4—C41105.4 (2)
C17—Fe2—C1640.63 (18)C40—Fe4—C4139.4 (2)
C11—Fe2—C16148.70 (19)C39—Fe4—C4166.5 (2)
C10—Fe2—C16115.62 (18)C42—Fe4—C36153.7 (2)
C12—Fe2—C16169.28 (18)C38—Fe4—C36162.5 (2)
C13—Fe2—C1668.36 (18)C37—Fe4—C3641.31 (19)
C9—Fe2—C14165.74 (17)C40—Fe4—C36106.6 (2)
C17—Fe2—C1468.49 (19)C39—Fe4—C36124.1 (2)
C11—Fe2—C14107.91 (19)C41—Fe4—C36118.5 (2)
C10—Fe2—C14128.07 (18)C42—Fe4—C33108.87 (16)
C12—Fe2—C14118.05 (17)C38—Fe4—C33122.4 (2)
C13—Fe2—C1440.43 (18)C37—Fe4—C3341.23 (17)
C16—Fe2—C1467.89 (18)C40—Fe4—C33161.0 (3)
C9—Fe2—C15127.67 (17)C39—Fe4—C33158.8 (3)
C17—Fe2—C1568.02 (19)C41—Fe4—C33125.3 (2)
C11—Fe2—C15116.4 (2)C36—Fe4—C3368.66 (16)
C10—Fe2—C15106.58 (18)C42—Fe4—C35165.2 (2)
C12—Fe2—C15150.17 (19)C38—Fe4—C35127.3 (2)
C13—Fe2—C1568.03 (18)C37—Fe4—C3569.0 (2)
C16—Fe2—C1539.95 (18)C40—Fe4—C35120.7 (2)
C14—Fe2—C1540.48 (17)C39—Fe4—C35109.2 (2)
C9—Fe2—C840.77 (15)C41—Fe4—C35153.5 (2)
C17—Fe2—C8109.65 (17)C36—Fe4—C3540.3 (2)
C11—Fe2—C868.42 (17)C33—Fe4—C3568.42 (17)
C10—Fe2—C868.34 (16)C42—Fe4—C34128.16 (18)
C12—Fe2—C840.94 (15)C38—Fe4—C34110.24 (19)
C13—Fe2—C8119.47 (16)C37—Fe4—C3469.3 (2)
C16—Fe2—C8129.93 (18)C40—Fe4—C34156.2 (2)
C14—Fe2—C8152.11 (16)C39—Fe4—C34123.5 (2)
C15—Fe2—C8166.75 (17)C41—Fe4—C34163.8 (2)
C18—S2—S197.4 (7)C36—Fe4—C3468.2 (2)
C18P—S2—S1P96.4 (7)C33—Fe4—C3440.94 (17)
O1—C18—C6126 (2)C35—Fe4—C3440.41 (17)
O1—C18—S2121.1 (17)C31—S4—S596.09 (13)
C6—C18—S2112.8 (15)C32—S5—S497.94 (13)
C7—S1—S295.5 (3)
C5—C1—C2—C31.2 (4)C6—C7—C18P—O1P167 (2)
Fe1—C1—C2—C358.8 (3)C8—C7—C18P—O1P14 (3)
C5—C1—C2—Fe160.0 (3)C6—C7—C18P—S21.1 (19)
C1—C2—C3—C40.4 (4)C8—C7—C18P—S2178.3 (8)
Fe1—C2—C3—C459.1 (3)S1P—S2—C18P—O1P168 (2)
C1—C2—C3—Fe158.7 (3)S1P—S2—C18P—C70.6 (18)
C2—C3—C4—C50.5 (4)C7—C6—S1P—S20.7 (6)
Fe1—C3—C4—C559.9 (3)C5—C6—S1P—S2176.6 (3)
C2—C3—C4—Fe159.3 (3)C29—C25—C26—C270.5 (4)
C2—C1—C5—C41.5 (4)Fe3—C25—C26—C2759.5 (3)
Fe1—C1—C5—C458.5 (3)C29—C25—C26—Fe359.0 (3)
C2—C1—C5—C6177.1 (4)C25—C26—C27—C281.0 (4)
Fe1—C1—C5—C6122.9 (4)Fe3—C26—C27—C2858.7 (3)
C2—C1—C5—Fe160.0 (3)C25—C26—C27—Fe359.7 (3)
C3—C4—C5—C11.2 (4)C26—C27—C28—C291.1 (4)
Fe1—C4—C5—C158.5 (3)Fe3—C27—C28—C2960.0 (2)
C3—C4—C5—C6177.4 (3)C26—C27—C28—Fe358.9 (3)
Fe1—C4—C5—C6122.8 (4)C26—C25—C29—C280.2 (4)
C3—C4—C5—Fe159.8 (3)Fe3—C25—C29—C2858.6 (2)
C1—C5—C6—C7140.5 (4)C26—C25—C29—C30179.8 (3)
C4—C5—C6—C737.8 (6)Fe3—C25—C29—C30121.5 (4)
Fe1—C5—C6—C7128.5 (4)C26—C25—C29—Fe358.7 (3)
C1—C5—C6—C1839.5 (12)C27—C28—C29—C250.8 (4)
C4—C5—C6—C18142.1 (11)Fe3—C28—C29—C2559.2 (2)
Fe1—C5—C6—C1851.4 (12)C27—C28—C29—C30179.2 (3)
C1—C5—C6—S1P42.3 (6)Fe3—C28—C29—C30120.9 (4)
C4—C5—C6—S1P139.4 (5)C27—C28—C29—Fe359.9 (3)
Fe1—C5—C6—S1P48.7 (5)C25—C29—C30—C31144.0 (4)
C5—C6—C7—C84.9 (7)C28—C29—C30—C3135.9 (6)
C18—C6—C7—C8175.1 (11)Fe3—C29—C30—C31125.7 (4)
S1P—C6—C7—C8178.1 (5)C25—C29—C30—C3237.9 (5)
C5—C6—C7—C18P175.6 (13)C28—C29—C30—C32142.2 (4)
S1P—C6—C7—C18P1.3 (13)Fe3—C29—C30—C3252.5 (5)
C5—C6—C7—S1175.6 (4)C29—C30—C31—C334.8 (6)
C18—C6—C7—S14.3 (11)C32—C30—C31—C33177.0 (4)
C6—C7—C8—C933.9 (6)C29—C30—C31—S4175.4 (3)
C18P—C7—C8—C9145.5 (13)C32—C30—C31—S42.8 (5)
S1—C7—C8—C9145.6 (4)C31—C30—C32—O3169.7 (4)
C6—C7—C8—C12147.9 (4)C29—C30—C32—O312.0 (6)
C18P—C7—C8—C1232.7 (14)C31—C30—C32—S54.4 (4)
S1—C7—C8—C1232.6 (5)C29—C30—C32—S5173.9 (3)
C6—C7—C8—Fe2123.7 (4)C30—C31—C33—C34147.4 (4)
C18P—C7—C8—Fe255.7 (14)S4—C31—C33—C3432.8 (5)
S1—C7—C8—Fe255.8 (4)C30—C31—C33—C3733.7 (6)
C12—C8—C9—C101.1 (4)S4—C31—C33—C37146.1 (4)
C7—C8—C9—C10179.6 (3)C30—C31—C33—Fe4122.7 (4)
Fe2—C8—C9—C1059.8 (3)S4—C31—C33—Fe457.1 (4)
C12—C8—C9—Fe258.7 (2)C37—C33—C34—C350.7 (5)
C7—C8—C9—Fe2119.7 (4)C31—C33—C34—C35179.7 (4)
C8—C9—C10—C110.8 (4)Fe4—C33—C34—C3559.2 (3)
Fe2—C9—C10—C1159.2 (3)C37—C33—C34—Fe458.6 (3)
C8—C9—C10—Fe259.9 (3)C31—C33—C34—Fe4120.5 (4)
C9—C10—C11—C120.1 (4)C33—C34—C35—C360.0 (5)
Fe2—C10—C11—C1259.3 (3)Fe4—C34—C35—C3658.9 (3)
C9—C10—C11—Fe259.2 (3)C33—C34—C35—Fe458.9 (3)
C10—C11—C12—C80.6 (4)C34—C35—C36—C370.7 (5)
Fe2—C11—C12—C859.7 (3)Fe4—C35—C36—C3758.4 (3)
C10—C11—C12—Fe259.2 (3)C34—C35—C36—Fe459.2 (3)
C9—C8—C12—C111.0 (4)C34—C33—C37—C361.1 (5)
C7—C8—C12—C11179.5 (3)C31—C33—C37—C36179.9 (4)
Fe2—C8—C12—C1159.6 (3)Fe4—C33—C37—C3660.1 (3)
C9—C8—C12—Fe258.5 (2)C34—C33—C37—Fe459.1 (3)
C7—C8—C12—Fe2120.0 (4)C31—C33—C37—Fe4120.0 (4)
C17—C13—C14—C150.6 (5)C35—C36—C37—C331.1 (5)
Fe2—C13—C14—C1559.6 (3)Fe4—C36—C37—C3360.2 (3)
C17—C13—C14—Fe259.0 (3)C35—C36—C37—Fe459.1 (3)
C13—C14—C15—C160.2 (5)C42—C38—C39—C400.8 (5)
Fe2—C14—C15—C1659.2 (3)Fe4—C38—C39—C4059.9 (4)
C13—C14—C15—Fe259.4 (3)C42—C38—C39—Fe460.6 (3)
C14—C15—C16—C170.2 (5)C38—C39—C40—C410.5 (6)
Fe2—C15—C16—C1758.8 (3)Fe4—C39—C40—C4159.5 (4)
C14—C15—C16—Fe259.1 (3)C38—C39—C40—Fe459.1 (3)
C15—C16—C17—C130.6 (4)C39—C40—C41—C420.0 (6)
Fe2—C16—C17—C1360.1 (3)Fe4—C40—C41—C4259.7 (3)
C15—C16—C17—Fe259.5 (3)C39—C40—C41—Fe459.7 (4)
C14—C13—C17—C160.7 (4)C40—C41—C42—C380.5 (5)
Fe2—C13—C17—C1660.3 (3)Fe4—C41—C42—C3859.5 (3)
C14—C13—C17—Fe259.6 (3)C40—C41—C42—Fe460.1 (4)
C24—C20—C21—C220.3 (5)C39—C38—C42—C410.8 (5)
Fe1—C20—C21—C2259.6 (3)Fe4—C38—C42—C4160.0 (3)
C24—C20—C21—Fe159.8 (3)C39—C38—C42—Fe460.8 (3)
C20—C21—C22—C230.2 (5)C47—C43—C44—C450.3 (4)
Fe1—C21—C22—C2359.3 (3)Fe3—C43—C44—C4559.5 (3)
C20—C21—C22—Fe159.5 (3)C47—C43—C44—Fe359.7 (3)
C21—C22—C23—C240.5 (5)C43—C44—C45—C460.0 (4)
Fe1—C22—C23—C2460.4 (3)Fe3—C44—C45—C4659.3 (3)
C21—C22—C23—Fe159.8 (3)C43—C44—C45—Fe359.2 (3)
C21—C20—C24—C230.6 (5)C44—C45—C46—C470.2 (4)
Fe1—C20—C24—C2359.1 (3)Fe3—C45—C46—C4759.8 (3)
C21—C20—C24—Fe159.7 (3)C44—C45—C46—Fe359.5 (3)
C22—C23—C24—C200.7 (5)C44—C43—C47—C460.4 (4)
Fe1—C23—C24—C2059.5 (3)Fe3—C43—C47—C4659.4 (3)
C22—C23—C24—Fe160.2 (3)C44—C43—C47—Fe359.8 (3)
C7—C6—C18—O1170.8 (17)C45—C46—C47—C430.4 (4)
C5—C6—C18—O19 (3)Fe3—C46—C47—C4359.4 (3)
C7—C6—C18—S25.7 (16)C45—C46—C47—Fe359.8 (3)
C5—C6—C18—S2174.2 (7)C30—C31—S4—S50.0 (3)
S1—S2—C18—O1172.3 (17)C33—C31—S4—S5179.8 (3)
S1—S2—C18—C64.4 (15)O3—C32—S5—S4170.7 (3)
C6—C7—S1—S21.0 (4)C30—C32—S5—S43.7 (3)
C8—C7—S1—S2178.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C36S—H36···O3i1.002.363.354 (6)170
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

The authors thank PAPIIT-DGAPA-UNAM (IN 217318), and CONACyT (251437) for their financial support of this work.

Funding information

Funding for this research was provided by: Consejo Nacional de Ciencia y Tecnología (award No. 251437); PAPIIT-DGAPA-UNAM (award No. IN-217318). .

References

First citationAgilent (2013). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.  Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationHe, X., Reeve, A. M. E., Desai, U. R., Kellogg, G. E. & Reynolds, K. A. (2004). Antimicrob. Agents Chemother. 48, 3093–3102.  Web of Science CrossRef PubMed CAS Google Scholar
First citationIida, K., Itoh, K., Kumagai, Y., Oyasu, R., Hattori, K., Kawai, K., Shimazui, T., Akaza, H. & Yamamoto, M. (2004). Cancer Res. 64, 6424–6431.  CrossRef Google Scholar
First citationKonstantinova, L. S., Berezin, A. A., Lysov, K. A. & Rakitin, O. A. (2007). Tetrahedron Lett. 48, 5851–5854.  CrossRef Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationTogni, A. & Hayashi, T. (1995). Ferrocenes. Weinheim: VCH  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds