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The title compound, [Fe2(C9H11NS2){Fe(C5H5)(C17H14P)}(CO)5], was prepared as an aza­dithiol­ato–iron model for the iron-only hydrogenase active site. The Fe2S2 unit exhibits a butterfly conformation and the ferrocenyldiphenyl­phosphine ligand is trans to the Fe—Fe bond. The Fe—Fe distance of 2.5160 (8) Å is longer than found in related model structures. Intra­molecular C—H...S and inter­molecular C—H...O hydrogen bonds are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808032698/ci2685sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808032698/ci2685Isup2.hkl
Contains datablock I

CCDC reference: 709668

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.048
  • wR factor = 0.079
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

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Alert level C Value of measurement temperature given = 298.000 Value of melting point given = 0.000 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 -- C14 .. 5.46 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe2 -- C10 .. 7.20 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe2 -- C11 .. 5.66 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The iron-only hydrogenases are enzymes that can efficiently catalyze the reversible reaction of hydrogen production (Cammack, 1999; Evans & Pickett, 2003). The active site at which this reaction takes place is composed of a butterfly shaped Fe2S2 unit covalently linked to a conventional Fe4S4 cluster by a bridged cysteinyl thioether (Peters et al., 1998; Nicolet et al., 1999). We have prepared the title complex as a structural model for the iron-only hydrogenases active site. Herein we report its crystal structure.

The molecular structure of the title complex is shown in Fig.1 and selected bond distances are listed in Table 1. In the Fe2S2 unit, the Fe—Fe distance of 2.5160 (8) Å is slightly longer than those observed in related complexes (Lawrence et al., 2001; Ott et al., 2004). The FcPPh2 (Fc is ferrocenyl and Ph is phenyl) ligand is in apical position (trans to Fe—Fe bond), with an Fe—P distance of 2.2565 (10) Å. The Fe1—C(O) distances are ~0.04 Å shorter than those found in a related complex (Hou et al., 2006), consistent with an increase in the charge of Fe1 because one of the CO ligands was replaced by the FcPPh2 ligand. The ferrocene unit is covalently linked to the Fe2S2 unit via the bridged diphenyl P atom, with an Fe1—P1—C23 angle of 118.32 (12)°. The N1 atom is displaced from the C5/C8/C9 plane by 0.168 (3) Å, and the sum of angles around N1 is 355.8°.

Intramolecular C—H···S and intermolecular C—H···O hydrogen bonds are observed.

Related literature top

For general background, see: Cammack (1999); Evans & Pickett (2003); Nicolet et al. (1999); Peters et al. (1998). For related structures, see: Hou et al. (2006); Lawrence et al. (2001); Ott et al. (2004).

Experimental top

The starting material [Fe2(µ-SCH2)2(4-CH3C6H4N)(CO)6] was obtained in 50% yield according to the literature method (Hou et al., 2006). The solution of Me3NO (120 mg, 1.06 mmol) was added to a red solution of [Fe2(µ-SCH2)2(4-CH3C6H4N)(CO)6] (0.50 g, 1.05 mmol) with FcPPh2 (0.39 g, 1.05 mmol) in CH3CN (100 ml) via syringe under a nitrogen atmosphere. The reaction mixture was stirred at ambient temperature until the TLC indicated there was no remaining carbonyl complex of starting material. The solvent was removed under vacuum and the resulted dark red residue was purified by column chromatography on silica gel eluting with CH2Cl2-hexane (1:5 v/v). A dark red solid was obtained from recrystallization in n-pentane-CH2Cl2. Single crystals of the title compound for X-ray analysis were grown from a CH2Cl2-hexane (1:5 v/v) solution by slow evaporation at ambient temperature.

Refinement top

H atoms were placed in geometrically calculated positions (C—H = 0.93–0.98 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl)

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, with displacement ellipsoids drawn at the 30% probability level.
Pentacarbonyl-1κ2C,2κ3C-(ferrocenyldiphenylphosphine-1κP)[µ-2-(4- methylphenyl)-2-azapropane-1,3-dithiolato- 1:2κ4S,S':S,S']diiron(I)(Fe—Fe) top
Crystal data top
[Fe3(C5H5)(C9H11NS2)(C17H14P)(CO)5]F(000) = 1672
Mr = 819.25Dx = 1.575 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2549 reflections
a = 13.600 (2) Åθ = 2.4–22.0°
b = 10.8964 (19) ŵ = 1.45 mm1
c = 23.396 (4) ÅT = 298 K
β = 94.741 (3)°Block, red
V = 3455.2 (11) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8202 independent reflections
Radiation source: fine-focus sealed tube4258 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
ϕ and ω scansθmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1718
Tmin = 0.760, Tmax = 0.868k = 914
21457 measured reflectionsl = 3130
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.0157P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max = 0.001
S = 0.80Δρmax = 0.66 e Å3
8202 reflectionsΔρmin = 0.39 e Å3
434 parameters
Crystal data top
[Fe3(C5H5)(C9H11NS2)(C17H14P)(CO)5]V = 3455.2 (11) Å3
Mr = 819.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.600 (2) ŵ = 1.45 mm1
b = 10.8964 (19) ÅT = 298 K
c = 23.396 (4) Å0.20 × 0.20 × 0.10 mm
β = 94.741 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8202 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
4258 reflections with I > 2σ(I)
Tmin = 0.760, Tmax = 0.868Rint = 0.070
21457 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 0.80Δρmax = 0.66 e Å3
8202 reflectionsΔρmin = 0.39 e Å3
434 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.20737 (4)0.18453 (5)0.30929 (2)0.03252 (14)
Fe20.20176 (4)0.09491 (5)0.40808 (2)0.03988 (16)
Fe30.08083 (4)0.09519 (5)0.11522 (2)0.04244 (16)
S10.34466 (7)0.12772 (9)0.36528 (4)0.0387 (2)
S20.15575 (7)0.00994 (9)0.32718 (4)0.0382 (2)
P10.26239 (7)0.19707 (9)0.22109 (4)0.0316 (2)
O10.2115 (2)0.1033 (3)0.49363 (13)0.0791 (11)
O20.2652 (3)0.3021 (3)0.48103 (14)0.1006 (13)
O30.0037 (2)0.1481 (3)0.42412 (14)0.0962 (12)
O40.2502 (2)0.4345 (2)0.34576 (12)0.0634 (9)
O50.0021 (2)0.2479 (3)0.27912 (12)0.0661 (9)
N10.3407 (2)0.1259 (3)0.34951 (12)0.0409 (8)
C10.4517 (4)0.3802 (4)0.56016 (18)0.0874 (16)
H1A0.44960.46710.55350.131*
H1B0.40660.35920.58810.131*
H1C0.51730.35660.57410.131*
C20.4224 (3)0.3132 (4)0.50438 (17)0.0536 (11)
C30.3533 (3)0.3595 (4)0.46376 (18)0.0529 (11)
H30.32410.43480.47060.063*
C40.3255 (3)0.2992 (4)0.41345 (16)0.0459 (10)
H40.27920.33460.38700.055*
C50.3662 (3)0.1853 (4)0.40172 (16)0.0394 (9)
C60.4364 (3)0.1384 (4)0.44210 (17)0.0485 (11)
H60.46580.06340.43530.058*
C70.4635 (3)0.2009 (4)0.49226 (17)0.0579 (12)
H70.51070.16670.51860.069*
C80.2455 (3)0.1362 (3)0.31877 (16)0.0479 (11)
H8A0.21560.21210.33040.057*
H8B0.25510.14360.27830.057*
C90.3917 (3)0.0175 (3)0.33541 (15)0.0448 (10)
H9A0.38830.01030.29400.054*
H9B0.46060.02660.34900.054*
C100.2131 (3)0.0291 (4)0.45986 (18)0.0539 (12)
C110.2391 (3)0.2194 (4)0.45270 (18)0.0651 (14)
C120.0758 (3)0.1262 (4)0.41723 (17)0.0561 (12)
C130.2339 (3)0.3362 (4)0.32971 (15)0.0385 (10)
C140.0838 (3)0.2218 (3)0.28947 (16)0.0431 (10)
C150.0207 (4)0.2515 (5)0.0789 (2)0.0749 (15)
H150.05680.31960.06300.090*
C160.0165 (4)0.1463 (5)0.0488 (2)0.0738 (15)
H160.01010.12870.00810.089*
C170.0633 (3)0.0727 (5)0.0861 (2)0.0736 (15)
H170.09580.00580.07660.088*
C180.0557 (3)0.1293 (5)0.1406 (2)0.0686 (14)
H180.08260.09790.17540.082*
C190.0044 (3)0.2407 (4)0.1355 (2)0.0662 (14)
H190.01150.29990.16640.079*
C200.1400 (3)0.0774 (4)0.12177 (17)0.0518 (11)
H200.10390.15460.11520.062*
C210.1848 (3)0.0097 (4)0.08032 (18)0.0551 (12)
H210.18540.03120.03970.066*
C220.2278 (3)0.0960 (4)0.10657 (15)0.0440 (10)
H220.26380.15980.08740.053*
C230.2103 (2)0.0944 (3)0.16603 (14)0.0331 (9)
C240.1549 (3)0.0139 (3)0.17502 (16)0.0429 (10)
H240.13100.04010.21150.051*
C250.3951 (2)0.1685 (3)0.22119 (14)0.0303 (8)
C260.4591 (3)0.2380 (3)0.25719 (15)0.0380 (9)
H260.43380.29980.27910.046*
C270.5593 (3)0.2175 (4)0.26120 (16)0.0471 (11)
H270.60110.26500.28570.056*
C280.5975 (3)0.1257 (4)0.22858 (17)0.0483 (11)
H280.66500.11030.23150.058*
C290.5357 (3)0.0582 (3)0.19212 (16)0.0455 (11)
H290.56180.00150.16930.055*
C300.4351 (3)0.0770 (3)0.18864 (15)0.0370 (9)
H300.39370.02830.16450.044*
C310.2548 (3)0.3488 (3)0.18691 (15)0.0343 (9)
C320.3189 (3)0.3814 (3)0.14616 (16)0.0477 (11)
H320.36770.32660.13710.057*
C330.3115 (3)0.4942 (4)0.11883 (17)0.0577 (12)
H330.35440.51410.09130.069*
C340.2412 (3)0.5761 (4)0.13229 (18)0.0591 (12)
H340.23640.65190.11400.071*
C350.1777 (3)0.5472 (4)0.17249 (18)0.0547 (12)
H350.13010.60340.18170.066*
C360.1843 (3)0.4339 (3)0.19954 (15)0.0427 (10)
H360.14050.41480.22670.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0317 (3)0.0340 (3)0.0323 (3)0.0013 (3)0.0052 (2)0.0022 (2)
Fe20.0415 (4)0.0483 (4)0.0305 (3)0.0029 (3)0.0065 (3)0.0030 (3)
Fe30.0349 (3)0.0523 (4)0.0393 (3)0.0000 (3)0.0020 (3)0.0046 (3)
S10.0357 (6)0.0427 (6)0.0374 (6)0.0044 (5)0.0019 (5)0.0000 (5)
S20.0405 (6)0.0395 (6)0.0343 (6)0.0058 (5)0.0014 (5)0.0002 (4)
P10.0296 (5)0.0336 (6)0.0319 (6)0.0006 (5)0.0038 (4)0.0019 (4)
O10.103 (3)0.087 (3)0.051 (2)0.012 (2)0.0248 (19)0.0228 (18)
O20.138 (3)0.099 (3)0.067 (3)0.033 (3)0.026 (2)0.042 (2)
O30.055 (2)0.151 (4)0.084 (3)0.020 (2)0.018 (2)0.018 (2)
O40.067 (2)0.046 (2)0.079 (2)0.0107 (16)0.0131 (17)0.0186 (16)
O50.0356 (18)0.080 (2)0.083 (2)0.0090 (16)0.0092 (17)0.0150 (17)
N10.049 (2)0.038 (2)0.036 (2)0.0013 (16)0.0032 (17)0.0055 (15)
C10.098 (4)0.094 (4)0.067 (4)0.003 (3)0.013 (3)0.034 (3)
C20.056 (3)0.057 (3)0.047 (3)0.001 (2)0.002 (2)0.018 (2)
C30.055 (3)0.047 (3)0.058 (3)0.009 (2)0.010 (2)0.012 (2)
C40.049 (3)0.044 (3)0.043 (3)0.006 (2)0.002 (2)0.001 (2)
C50.041 (2)0.040 (3)0.037 (2)0.004 (2)0.0059 (19)0.0015 (19)
C60.042 (3)0.049 (3)0.054 (3)0.007 (2)0.001 (2)0.014 (2)
C70.050 (3)0.062 (3)0.059 (3)0.004 (2)0.011 (2)0.008 (2)
C80.063 (3)0.035 (3)0.044 (3)0.001 (2)0.006 (2)0.0051 (19)
C90.044 (2)0.046 (3)0.046 (3)0.012 (2)0.014 (2)0.009 (2)
C100.045 (3)0.080 (4)0.039 (3)0.002 (2)0.016 (2)0.006 (2)
C110.072 (3)0.083 (4)0.043 (3)0.010 (3)0.022 (3)0.013 (3)
C120.056 (3)0.074 (3)0.039 (3)0.002 (3)0.005 (2)0.006 (2)
C130.032 (2)0.044 (3)0.040 (2)0.004 (2)0.0056 (18)0.004 (2)
C140.045 (3)0.037 (3)0.050 (3)0.006 (2)0.012 (2)0.0042 (19)
C150.073 (4)0.067 (4)0.082 (4)0.013 (3)0.011 (3)0.016 (3)
C160.065 (4)0.094 (5)0.058 (3)0.017 (3)0.021 (3)0.009 (3)
C170.038 (3)0.087 (4)0.093 (4)0.001 (3)0.016 (3)0.020 (3)
C180.035 (3)0.098 (4)0.073 (4)0.004 (3)0.005 (2)0.013 (3)
C190.045 (3)0.071 (4)0.080 (4)0.020 (3)0.012 (3)0.021 (3)
C200.055 (3)0.042 (3)0.056 (3)0.001 (2)0.011 (2)0.013 (2)
C210.047 (3)0.076 (3)0.042 (3)0.003 (2)0.002 (2)0.024 (2)
C220.038 (2)0.058 (3)0.036 (2)0.005 (2)0.0070 (19)0.006 (2)
C230.030 (2)0.037 (2)0.032 (2)0.0003 (18)0.0013 (17)0.0005 (18)
C240.046 (3)0.045 (3)0.036 (2)0.002 (2)0.001 (2)0.0014 (19)
C250.030 (2)0.032 (2)0.030 (2)0.0019 (17)0.0070 (17)0.0068 (16)
C260.037 (2)0.036 (2)0.042 (2)0.0003 (19)0.010 (2)0.0054 (18)
C270.036 (2)0.052 (3)0.052 (3)0.010 (2)0.003 (2)0.001 (2)
C280.025 (2)0.059 (3)0.061 (3)0.006 (2)0.004 (2)0.009 (2)
C290.039 (3)0.046 (3)0.053 (3)0.012 (2)0.015 (2)0.000 (2)
C300.037 (2)0.036 (2)0.038 (2)0.0036 (18)0.0033 (18)0.0005 (18)
C310.032 (2)0.035 (2)0.036 (2)0.0001 (17)0.0041 (18)0.0048 (17)
C320.042 (3)0.049 (3)0.053 (3)0.013 (2)0.007 (2)0.014 (2)
C330.053 (3)0.065 (3)0.057 (3)0.006 (3)0.014 (2)0.027 (2)
C340.060 (3)0.050 (3)0.067 (3)0.008 (2)0.001 (3)0.023 (2)
C350.054 (3)0.045 (3)0.065 (3)0.021 (2)0.004 (2)0.009 (2)
C360.036 (2)0.050 (3)0.043 (2)0.008 (2)0.0061 (19)0.001 (2)
Geometric parameters (Å, º) top
Fe1—C131.750 (4)C7—H70.93
Fe1—C141.754 (4)C8—H8A0.97
Fe1—P12.2565 (10)C8—H8B0.97
Fe1—S12.2762 (11)C9—H9A0.97
Fe1—S22.2818 (11)C9—H9B0.97
Fe1—Fe22.5160 (8)C15—C191.399 (5)
Fe2—C111.761 (5)C15—C161.417 (6)
Fe2—C121.777 (5)C15—H150.98
Fe2—C101.813 (5)C16—C171.379 (6)
Fe2—S22.2546 (11)C16—H160.98
Fe2—S12.2867 (11)C17—C181.413 (6)
Fe3—C222.025 (4)C17—H170.98
Fe3—C182.030 (4)C18—C191.410 (5)
Fe3—C162.034 (4)C18—H180.98
Fe3—C172.036 (4)C19—H190.98
Fe3—C242.038 (4)C20—C211.398 (5)
Fe3—C212.040 (4)C20—C241.425 (5)
Fe3—C232.041 (3)C20—H200.98
Fe3—C192.043 (4)C21—C221.409 (5)
Fe3—C152.044 (4)C21—H210.98
Fe3—C202.047 (4)C22—C231.431 (4)
S1—C91.864 (3)C22—H220.98
S2—C81.860 (4)C23—C241.425 (4)
P1—C231.806 (3)C24—H240.98
P1—C251.832 (3)C25—C261.385 (4)
P1—C311.836 (3)C25—C301.392 (4)
O1—C101.132 (4)C26—C271.376 (5)
O2—C111.157 (4)C26—H260.93
O3—C121.132 (4)C27—C281.385 (5)
O4—C131.151 (4)C27—H270.93
O5—C141.153 (4)C28—C291.363 (5)
N1—C51.400 (4)C28—H280.93
N1—C91.421 (4)C29—C301.380 (5)
N1—C81.433 (4)C29—H290.93
C1—C21.519 (5)C30—H300.93
C1—H1A0.96C31—C361.382 (4)
C1—H1B0.96C31—C321.391 (4)
C1—H1C0.96C32—C331.386 (5)
C2—C31.376 (5)C32—H320.93
C2—C71.385 (5)C33—C341.363 (5)
C3—C41.374 (5)C33—H330.93
C3—H30.93C34—C351.364 (5)
C4—C51.396 (5)C34—H340.93
C4—H40.93C35—C361.386 (4)
C5—C61.384 (5)C35—H350.93
C6—C71.381 (5)C36—H360.93
C6—H60.93
C13—Fe1—C1491.41 (17)N1—C8—S2117.6 (2)
C13—Fe1—P196.67 (12)N1—C8—H8A107.9
C14—Fe1—P197.31 (12)S2—C8—H8A107.9
C13—Fe1—S187.66 (12)N1—C8—H8B107.9
C14—Fe1—S1159.67 (12)S2—C8—H8B107.9
P1—Fe1—S1102.97 (4)H8A—C8—H8B107.2
C13—Fe1—S2152.46 (12)N1—C9—S1115.4 (2)
C14—Fe1—S287.77 (12)N1—C9—H9A108.4
P1—Fe1—S2110.75 (4)S1—C9—H9A108.4
S1—Fe1—S283.80 (4)N1—C9—H9B108.4
C13—Fe1—Fe297.87 (12)S1—C9—H9B108.4
C14—Fe1—Fe2103.39 (12)H9A—C9—H9B107.5
P1—Fe1—Fe2154.30 (4)O1—C10—Fe2173.4 (4)
S1—Fe1—Fe256.73 (3)O2—C11—Fe2178.3 (4)
S2—Fe1—Fe255.80 (3)O3—C12—Fe2178.3 (4)
C11—Fe2—C1290.8 (2)O4—C13—Fe1176.7 (3)
C11—Fe2—C10100.0 (2)O5—C14—Fe1176.7 (4)
C12—Fe2—C1095.26 (18)C19—C15—C16107.3 (5)
C11—Fe2—S2159.16 (15)C19—C15—Fe369.9 (3)
C12—Fe2—S289.71 (14)C16—C15—Fe369.3 (3)
C10—Fe2—S2100.70 (14)C19—C15—H15126.3
C11—Fe2—S185.74 (13)C16—C15—H15126.4
C12—Fe2—S1152.32 (14)Fe3—C15—H15126.4
C10—Fe2—S1112.39 (13)C17—C16—C15108.7 (5)
S2—Fe2—S184.18 (4)C17—C16—Fe370.3 (3)
C11—Fe2—Fe1102.51 (14)C15—C16—Fe370.0 (3)
C12—Fe2—Fe197.99 (13)C17—C16—H16125.6
C10—Fe2—Fe1153.62 (13)C15—C16—H16125.7
S2—Fe2—Fe156.83 (3)Fe3—C16—H16125.6
S1—Fe2—Fe156.34 (3)C16—C17—C18108.3 (5)
C22—Fe3—C18164.24 (18)C16—C17—Fe370.1 (3)
C22—Fe3—C16120.53 (19)C18—C17—Fe369.5 (2)
C18—Fe3—C1667.69 (19)C16—C17—H17126.0
C22—Fe3—C17153.86 (18)C18—C17—H17125.7
C18—Fe3—C1740.67 (16)Fe3—C17—H17125.8
C16—Fe3—C1739.61 (17)C19—C18—C17107.4 (4)
C22—Fe3—C2468.59 (15)C19—C18—Fe370.2 (2)
C18—Fe3—C24108.54 (17)C17—C18—Fe369.9 (2)
C16—Fe3—C24159.7 (2)C19—C18—H18126.3
C17—Fe3—C24124.54 (19)C17—C18—H18126.3
C22—Fe3—C2140.55 (13)Fe3—C18—H18126.3
C18—Fe3—C21154.22 (19)C15—C19—C18108.4 (4)
C16—Fe3—C21106.06 (18)C15—C19—Fe370.0 (2)
C17—Fe3—C21118.59 (18)C18—C19—Fe369.3 (2)
C24—Fe3—C2168.17 (16)C15—C19—H19125.9
C22—Fe3—C2341.20 (12)C18—C19—H19125.8
C18—Fe3—C23126.57 (17)Fe3—C19—H19126.0
C16—Fe3—C23157.2 (2)C21—C20—C24108.1 (4)
C17—Fe3—C23162.63 (19)C21—C20—Fe369.8 (2)
C24—Fe3—C2340.89 (12)C24—C20—Fe369.3 (2)
C21—Fe3—C2368.77 (14)C21—C20—H20125.8
C22—Fe3—C19127.14 (18)C24—C20—H20126.0
C18—Fe3—C1940.50 (15)Fe3—C20—H20126.1
C16—Fe3—C1967.59 (18)C20—C21—C22108.5 (4)
C17—Fe3—C1967.78 (18)C20—C21—Fe370.2 (2)
C24—Fe3—C19123.45 (18)C22—C21—Fe369.1 (2)
C21—Fe3—C19162.4 (2)C20—C21—H21125.9
C23—Fe3—C19110.29 (16)C22—C21—H21125.6
C22—Fe3—C15108.63 (18)Fe3—C21—H21125.7
C18—Fe3—C1567.97 (19)C21—C22—C23108.5 (3)
C16—Fe3—C1540.67 (16)C21—C22—Fe370.3 (2)
C17—Fe3—C1567.7 (2)C23—C22—Fe370.00 (19)
C24—Fe3—C15158.38 (19)C21—C22—H22125.9
C21—Fe3—C15124.6 (2)C23—C22—H22125.6
C23—Fe3—C15122.80 (18)Fe3—C22—H22125.7
C19—Fe3—C1540.03 (16)C24—C23—C22106.6 (3)
C22—Fe3—C2068.06 (16)C24—C23—P1126.1 (3)
C18—Fe3—C20120.63 (19)C22—C23—P1126.8 (3)
C16—Fe3—C20122.40 (18)C24—C23—Fe369.4 (2)
C17—Fe3—C20106.01 (18)C22—C23—Fe368.8 (2)
C24—Fe3—C2040.84 (13)P1—C23—Fe3132.96 (18)
C21—Fe3—C2040.00 (14)C23—C24—C20108.2 (3)
C23—Fe3—C2068.76 (14)C23—C24—Fe369.7 (2)
C19—Fe3—C20157.4 (2)C20—C24—Fe369.9 (2)
C15—Fe3—C20159.8 (2)C23—C24—H24125.9
C9—S1—Fe1107.79 (13)C20—C24—H24125.9
C9—S1—Fe2111.20 (12)Fe3—C24—H24125.9
Fe1—S1—Fe266.93 (3)C26—C25—C30118.0 (3)
C8—S2—Fe2108.94 (12)C26—C25—P1118.5 (3)
C8—S2—Fe1116.93 (13)C30—C25—P1123.4 (3)
Fe2—S2—Fe167.37 (3)C27—C26—C25121.5 (3)
C23—P1—C25102.96 (16)C27—C26—H26119.3
C23—P1—C31104.03 (16)C25—C26—H26119.3
C25—P1—C31100.01 (15)C26—C27—C28119.6 (4)
C23—P1—Fe1118.32 (12)C26—C27—H27120.2
C25—P1—Fe1112.95 (11)C28—C27—H27120.2
C31—P1—Fe1116.22 (12)C29—C28—C27119.7 (4)
C5—N1—C9119.7 (3)C29—C28—H28120.2
C5—N1—C8123.4 (3)C27—C28—H28120.2
C9—N1—C8112.7 (3)C28—C29—C30120.9 (4)
C2—C1—H1A109.5C28—C29—H29119.5
C2—C1—H1B109.5C30—C29—H29119.5
H1A—C1—H1B109.5C29—C30—C25120.3 (4)
C2—C1—H1C109.5C29—C30—H30119.9
H1A—C1—H1C109.5C25—C30—H30119.9
H1B—C1—H1C109.5C36—C31—C32117.4 (3)
C3—C2—C7116.6 (4)C36—C31—P1121.7 (3)
C3—C2—C1122.2 (4)C32—C31—P1120.8 (3)
C7—C2—C1121.2 (4)C33—C32—C31121.1 (4)
C4—C3—C2122.7 (4)C33—C32—H32119.4
C4—C3—H3118.7C31—C32—H32119.4
C2—C3—H3118.7C34—C33—C32120.0 (4)
C3—C4—C5120.6 (4)C34—C33—H33120.0
C3—C4—H4119.7C32—C33—H33120.0
C5—C4—H4119.7C33—C34—C35120.3 (4)
C6—C5—C4117.1 (4)C33—C34—H34119.9
C6—C5—N1122.2 (4)C35—C34—H34119.9
C4—C5—N1120.6 (4)C34—C35—C36120.0 (4)
C7—C6—C5121.3 (4)C34—C35—H35120.0
C7—C6—H6119.4C36—C35—H35120.0
C5—C6—H6119.4C31—C36—C35121.3 (4)
C6—C7—C2121.7 (4)C31—C36—H36119.4
C6—C7—H7119.1C35—C36—H36119.4
C2—C7—H7119.1
C13—Fe1—Fe2—C115.79 (19)C20—Fe3—C18—C1778.6 (3)
C14—Fe1—Fe2—C1199.1 (2)C16—C15—C19—C180.7 (5)
P1—Fe1—Fe2—C11118.10 (17)Fe3—C15—C19—C1858.8 (3)
S1—Fe1—Fe2—C1176.16 (16)C16—C15—C19—Fe359.5 (3)
S2—Fe1—Fe2—C11177.00 (16)C17—C18—C19—C151.0 (5)
C13—Fe1—Fe2—C1286.84 (18)Fe3—C18—C19—C1559.3 (3)
C14—Fe1—Fe2—C126.51 (19)C17—C18—C19—Fe360.3 (3)
P1—Fe1—Fe2—C12149.28 (16)C22—Fe3—C19—C1573.8 (3)
S1—Fe1—Fe2—C12168.78 (14)C18—Fe3—C19—C15119.7 (4)
S2—Fe1—Fe2—C1284.38 (14)C16—Fe3—C19—C1538.3 (3)
C13—Fe1—Fe2—C10153.7 (3)C17—Fe3—C19—C1581.3 (3)
C14—Fe1—Fe2—C10112.9 (3)C24—Fe3—C19—C15161.0 (3)
P1—Fe1—Fe2—C1029.8 (3)C21—Fe3—C19—C1533.6 (7)
S1—Fe1—Fe2—C1071.8 (3)C23—Fe3—C19—C15117.2 (3)
S2—Fe1—Fe2—C1035.1 (3)C20—Fe3—C19—C15159.5 (4)
C13—Fe1—Fe2—S2171.21 (12)C22—Fe3—C19—C18166.5 (3)
C14—Fe1—Fe2—S277.86 (13)C16—Fe3—C19—C1881.4 (3)
P1—Fe1—Fe2—S264.90 (8)C17—Fe3—C19—C1838.4 (3)
S1—Fe1—Fe2—S2106.84 (4)C24—Fe3—C19—C1879.2 (3)
C13—Fe1—Fe2—S181.95 (12)C21—Fe3—C19—C18153.3 (5)
C14—Fe1—Fe2—S1175.30 (13)C23—Fe3—C19—C18123.0 (3)
P1—Fe1—Fe2—S141.94 (8)C15—Fe3—C19—C18119.7 (4)
S2—Fe1—Fe2—S1106.84 (4)C20—Fe3—C19—C1839.7 (6)
C13—Fe1—S1—C9152.98 (16)C22—Fe3—C20—C2137.4 (2)
C14—Fe1—S1—C9119.3 (4)C18—Fe3—C20—C21157.3 (3)
P1—Fe1—S1—C956.67 (12)C16—Fe3—C20—C2175.7 (3)
S2—Fe1—S1—C953.25 (12)C17—Fe3—C20—C21115.6 (3)
Fe2—Fe1—S1—C9106.02 (12)C24—Fe3—C20—C21119.6 (3)
C13—Fe1—S1—Fe2101.00 (11)C23—Fe3—C20—C2181.9 (2)
C14—Fe1—S1—Fe213.3 (4)C19—Fe3—C20—C21173.9 (4)
P1—Fe1—S1—Fe2162.70 (4)C15—Fe3—C20—C2147.0 (6)
S2—Fe1—S1—Fe252.78 (3)C22—Fe3—C20—C2482.2 (2)
C11—Fe2—S1—C9150.9 (2)C18—Fe3—C20—C2483.1 (3)
C12—Fe2—S1—C9125.5 (3)C16—Fe3—C20—C24164.7 (3)
C10—Fe2—S1—C951.8 (2)C17—Fe3—C20—C24124.8 (3)
S2—Fe2—S1—C947.37 (13)C21—Fe3—C20—C24119.6 (3)
Fe1—Fe2—S1—C9101.01 (13)C23—Fe3—C20—C2437.7 (2)
C11—Fe2—S1—Fe1108.09 (16)C19—Fe3—C20—C2454.3 (5)
C12—Fe2—S1—Fe124.5 (3)C15—Fe3—C20—C24166.6 (5)
C10—Fe2—S1—Fe1152.84 (15)C24—C20—C21—C220.1 (5)
S2—Fe2—S1—Fe153.64 (3)Fe3—C20—C21—C2258.7 (3)
C11—Fe2—S2—C8120.3 (4)C24—C20—C21—Fe358.8 (3)
C12—Fe2—S2—C8148.17 (19)C22—Fe3—C21—C20119.9 (4)
C10—Fe2—S2—C852.87 (18)C18—Fe3—C21—C2049.8 (5)
S1—Fe2—S2—C858.87 (13)C16—Fe3—C21—C20121.6 (3)
Fe1—Fe2—S2—C8112.07 (13)C17—Fe3—C21—C2080.8 (3)
C11—Fe2—S2—Fe18.2 (4)C24—Fe3—C21—C2037.8 (2)
C12—Fe2—S2—Fe199.76 (14)C23—Fe3—C21—C2081.9 (2)
C10—Fe2—S2—Fe1164.94 (13)C19—Fe3—C21—C20172.2 (5)
S1—Fe2—S2—Fe153.20 (3)C15—Fe3—C21—C20162.2 (3)
C13—Fe1—S2—C8119.6 (3)C18—Fe3—C21—C22169.7 (4)
C14—Fe1—S2—C8151.61 (18)C16—Fe3—C21—C22118.5 (3)
P1—Fe1—S2—C854.64 (14)C17—Fe3—C21—C22159.3 (3)
S1—Fe1—S2—C846.91 (14)C24—Fe3—C21—C2282.1 (3)
Fe2—Fe1—S2—C8100.52 (14)C23—Fe3—C21—C2238.0 (2)
C13—Fe1—S2—Fe219.1 (3)C19—Fe3—C21—C2252.3 (7)
C14—Fe1—S2—Fe2107.87 (12)C15—Fe3—C21—C2277.9 (3)
P1—Fe1—S2—Fe2155.17 (4)C20—Fe3—C21—C22119.9 (4)
S1—Fe1—S2—Fe253.61 (3)C20—C21—C22—C230.4 (5)
C13—Fe1—P1—C23153.80 (18)Fe3—C21—C22—C2359.8 (3)
C14—Fe1—P1—C2361.51 (18)C20—C21—C22—Fe359.4 (3)
S1—Fe1—P1—C23117.07 (13)C18—Fe3—C22—C21163.4 (6)
S2—Fe1—P1—C2328.86 (14)C16—Fe3—C22—C2178.7 (3)
Fe2—Fe1—P1—C2382.08 (15)C17—Fe3—C22—C2144.7 (5)
C13—Fe1—P1—C2585.87 (17)C24—Fe3—C22—C2181.0 (3)
C14—Fe1—P1—C25178.16 (17)C23—Fe3—C22—C21119.3 (3)
S1—Fe1—P1—C253.25 (13)C19—Fe3—C22—C21162.5 (3)
S2—Fe1—P1—C2591.46 (13)C15—Fe3—C22—C21121.8 (3)
Fe2—Fe1—P1—C2538.24 (16)C20—Fe3—C22—C2136.9 (2)
C13—Fe1—P1—C3128.89 (18)C18—Fe3—C22—C2344.1 (7)
C14—Fe1—P1—C3163.40 (18)C16—Fe3—C22—C23162.0 (2)
S1—Fe1—P1—C31118.01 (13)C17—Fe3—C22—C23164.0 (4)
S2—Fe1—P1—C31153.78 (13)C24—Fe3—C22—C2338.3 (2)
Fe2—Fe1—P1—C31153.00 (13)C21—Fe3—C22—C23119.3 (3)
C7—C2—C3—C40.1 (6)C19—Fe3—C22—C2378.2 (3)
C1—C2—C3—C4179.4 (4)C15—Fe3—C22—C23118.9 (3)
C2—C3—C4—C50.9 (6)C20—Fe3—C22—C2382.4 (2)
C3—C4—C5—C61.4 (5)C21—C22—C23—C240.6 (4)
C3—C4—C5—N1177.6 (3)Fe3—C22—C23—C2459.4 (2)
C9—N1—C5—C63.7 (5)C21—C22—C23—P1171.5 (3)
C8—N1—C5—C6151.7 (3)Fe3—C22—C23—P1128.5 (3)
C9—N1—C5—C4172.3 (3)C21—C22—C23—Fe360.0 (3)
C8—N1—C5—C432.3 (5)C25—P1—C23—C24109.2 (3)
C4—C5—C6—C71.1 (6)C31—P1—C23—C24146.8 (3)
N1—C5—C6—C7177.2 (3)Fe1—P1—C23—C2416.1 (4)
C5—C6—C7—C20.3 (6)C25—P1—C23—C2261.3 (3)
C3—C2—C7—C60.2 (6)C31—P1—C23—C2242.6 (4)
C1—C2—C7—C6179.0 (4)Fe1—P1—C23—C22173.3 (3)
C5—N1—C8—S298.7 (4)C25—P1—C23—Fe3155.9 (2)
C9—N1—C8—S258.1 (4)C31—P1—C23—Fe351.9 (3)
Fe2—S2—C8—N120.0 (3)Fe1—P1—C23—Fe378.7 (3)
Fe1—S2—C8—N153.6 (3)C22—Fe3—C23—C24118.2 (3)
C5—N1—C9—S184.2 (4)C18—Fe3—C23—C2475.4 (3)
C8—N1—C9—S173.6 (3)C16—Fe3—C23—C24161.7 (4)
Fe1—S1—C9—N179.0 (3)C17—Fe3—C23—C2437.8 (6)
Fe2—S1—C9—N17.5 (3)C21—Fe3—C23—C2480.8 (2)
C22—Fe3—C15—C19126.1 (3)C19—Fe3—C23—C24118.1 (2)
C18—Fe3—C15—C1937.5 (3)C15—Fe3—C23—C24161.0 (2)
C16—Fe3—C15—C19118.4 (4)C20—Fe3—C23—C2437.7 (2)
C17—Fe3—C15—C1981.6 (3)C18—Fe3—C23—C22166.4 (3)
C24—Fe3—C15—C1947.4 (6)C16—Fe3—C23—C2243.4 (5)
C21—Fe3—C15—C19168.2 (3)C17—Fe3—C23—C22156.0 (5)
C23—Fe3—C15—C1982.8 (3)C24—Fe3—C23—C22118.2 (3)
C20—Fe3—C15—C19157.0 (5)C21—Fe3—C23—C2237.5 (2)
C22—Fe3—C15—C16115.5 (3)C19—Fe3—C23—C22123.7 (3)
C18—Fe3—C15—C1680.9 (3)C15—Fe3—C23—C2280.8 (3)
C17—Fe3—C15—C1636.9 (3)C20—Fe3—C23—C2280.5 (2)
C24—Fe3—C15—C16165.8 (4)C22—Fe3—C23—P1121.1 (4)
C21—Fe3—C15—C1673.3 (4)C18—Fe3—C23—P145.3 (4)
C23—Fe3—C15—C16158.8 (3)C16—Fe3—C23—P177.7 (5)
C19—Fe3—C15—C16118.4 (4)C17—Fe3—C23—P182.9 (6)
C20—Fe3—C15—C1638.6 (7)C24—Fe3—C23—P1120.7 (3)
C19—C15—C16—C170.1 (5)C21—Fe3—C23—P1158.6 (3)
Fe3—C15—C16—C1759.8 (3)C19—Fe3—C23—P12.6 (3)
C19—C15—C16—Fe359.9 (3)C15—Fe3—C23—P140.3 (3)
C22—Fe3—C16—C17157.2 (3)C20—Fe3—C23—P1158.4 (3)
C18—Fe3—C16—C1737.8 (3)C22—C23—C24—C200.5 (4)
C24—Fe3—C16—C1745.4 (6)P1—C23—C24—C20171.6 (3)
C21—Fe3—C16—C17115.7 (3)Fe3—C23—C24—C2059.5 (3)
C23—Fe3—C16—C17171.0 (3)C22—C23—C24—Fe359.0 (2)
C19—Fe3—C16—C1781.8 (3)P1—C23—C24—Fe3128.9 (3)
C15—Fe3—C16—C17119.5 (4)C21—C20—C24—C230.2 (4)
C20—Fe3—C16—C1775.3 (4)Fe3—C20—C24—C2359.4 (3)
C22—Fe3—C16—C1583.3 (3)C21—C20—C24—Fe359.1 (3)
C18—Fe3—C16—C1581.7 (3)C22—Fe3—C24—C2338.56 (19)
C17—Fe3—C16—C15119.5 (4)C18—Fe3—C24—C23124.9 (2)
C24—Fe3—C16—C15164.9 (4)C16—Fe3—C24—C23159.4 (5)
C21—Fe3—C16—C15124.8 (3)C17—Fe3—C24—C23167.2 (2)
C23—Fe3—C16—C1551.5 (6)C21—Fe3—C24—C2382.3 (2)
C19—Fe3—C16—C1537.7 (3)C19—Fe3—C24—C2382.6 (3)
C20—Fe3—C16—C15165.2 (3)C15—Fe3—C24—C2348.1 (5)
C15—C16—C17—C180.6 (5)C20—Fe3—C24—C23119.3 (3)
Fe3—C16—C17—C1859.1 (3)C22—Fe3—C24—C2080.8 (2)
C15—C16—C17—Fe359.7 (3)C18—Fe3—C24—C20115.7 (3)
C22—Fe3—C17—C1649.2 (6)C16—Fe3—C24—C2040.1 (6)
C18—Fe3—C17—C16119.5 (5)C17—Fe3—C24—C2073.5 (3)
C24—Fe3—C17—C16162.6 (3)C21—Fe3—C24—C2037.0 (2)
C21—Fe3—C17—C1680.5 (4)C23—Fe3—C24—C20119.3 (3)
C23—Fe3—C17—C16168.3 (5)C19—Fe3—C24—C20158.0 (3)
C19—Fe3—C17—C1681.2 (3)C15—Fe3—C24—C20167.4 (5)
C15—Fe3—C17—C1637.8 (3)C23—P1—C25—C26176.8 (3)
C20—Fe3—C17—C16121.8 (3)C31—P1—C25—C2669.7 (3)
C22—Fe3—C17—C18168.7 (4)Fe1—P1—C25—C2654.5 (3)
C16—Fe3—C17—C18119.5 (5)C23—P1—C25—C306.0 (3)
C24—Fe3—C17—C1877.9 (3)C31—P1—C25—C30113.1 (3)
C21—Fe3—C17—C18160.0 (3)Fe1—P1—C25—C30122.8 (3)
C23—Fe3—C17—C1848.8 (7)C30—C25—C26—C270.3 (5)
C19—Fe3—C17—C1838.3 (3)P1—C25—C26—C27177.1 (3)
C15—Fe3—C17—C1881.7 (3)C25—C26—C27—C280.1 (6)
C20—Fe3—C17—C18118.6 (3)C26—C27—C28—C291.2 (6)
C16—C17—C18—C191.0 (5)C27—C28—C29—C302.2 (6)
Fe3—C17—C18—C1960.5 (3)C28—C29—C30—C252.1 (6)
C16—C17—C18—Fe359.6 (3)C26—C25—C30—C290.8 (5)
C22—Fe3—C18—C1943.4 (8)P1—C25—C30—C29178.0 (3)
C16—Fe3—C18—C1981.1 (3)C23—P1—C31—C36104.2 (3)
C17—Fe3—C18—C19118.0 (4)C25—P1—C31—C36149.6 (3)
C24—Fe3—C18—C19120.2 (3)Fe1—P1—C31—C3627.7 (3)
C21—Fe3—C18—C19161.8 (4)C23—P1—C31—C3274.4 (3)
C23—Fe3—C18—C1978.3 (3)C25—P1—C31—C3231.8 (3)
C15—Fe3—C18—C1937.1 (3)Fe1—P1—C31—C32153.6 (3)
C20—Fe3—C18—C19163.4 (3)C36—C31—C32—C330.8 (6)
C22—Fe3—C18—C17161.4 (6)P1—C31—C32—C33177.8 (3)
C16—Fe3—C18—C1736.9 (3)C31—C32—C33—C340.9 (6)
C24—Fe3—C18—C17121.8 (3)C32—C33—C34—C350.2 (7)
C21—Fe3—C18—C1743.8 (6)C33—C34—C35—C360.4 (7)
C23—Fe3—C18—C17163.8 (3)C32—C31—C36—C350.2 (6)
C19—Fe3—C18—C17118.0 (4)P1—C31—C36—C35178.5 (3)
C15—Fe3—C18—C1780.9 (3)C34—C35—C36—C310.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O2i0.982.533.224 (5)128
C24—H24···S20.982.723.561 (4)144
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formula[Fe3(C5H5)(C9H11NS2)(C17H14P)(CO)5]
Mr819.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)13.600 (2), 10.8964 (19), 23.396 (4)
β (°) 94.741 (3)
V3)3455.2 (11)
Z4
Radiation typeMo Kα
µ (mm1)1.45
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.760, 0.868
No. of measured, independent and
observed [I > 2σ(I)] reflections
21457, 8202, 4258
Rint0.070
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.079, 0.80
No. of reflections8202
No. of parameters434
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.66, 0.39

Computer programs: SMART (Bruker, 1997), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Fe1—C131.750 (4)Fe2—C111.761 (5)
Fe1—P12.2565 (10)Fe2—C121.777 (5)
Fe1—S12.2762 (11)Fe2—C101.813 (5)
Fe1—S22.2818 (11)Fe2—S22.2546 (11)
Fe1—Fe22.5160 (8)Fe2—S12.2867 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O2i0.982.533.224 (5)128
C24—H24···S20.982.723.561 (4)144
Symmetry code: (i) x, y+1/2, z1/2.
 

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