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Acta Cryst. (2007). E63, m1959-m1960
https://doi.org/10.1107/S1600536807029431
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Penta­carbonyl-1κ2C,2κ3C-(diphenyl­phosphine-1κP)(μ-2-propyl-2-aza­propane-1,3-dithiol­ato-1κ2S,S′:2κ2S,S′)diiron(Fe—Fe)

Z. Wang, J.-H. Liu and L.-C. Sun
The title compound, [Fe2(C5H11NS2)(C12H11P)(CO)5], has been prepared and characterized as a model compound of the iron hydrogenase active site through controlled CO ligand displacement of (μ-SCH2)2N(CH2CH2CH3)[Fe2(CO)6] with diphenyl­phosphine. The central Fe2S2 structure is in a butterfly conformation, and each Fe atom displays pseudo-square-pyramidal geometry. The phosphine group occupies an apical position. The propyl group on the bridging N atom is in an equatorial position and takes a zigzag form. In the crystal packing, adjacent pairs of mol­ecules are associated by S...S (3.625 Å) inter­molecular nonbonded weak inter­actions.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029431/wk2062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029431/wk2062Isup2.hkl
Contains datablock I

CCDC reference: 293747

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.087
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found




Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C9     -   C10     ..       9.62 su


Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.75 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C1      ..       5.44 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C2      ..       6.50 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   C4      ..       5.14 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C8      ..       6.53 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       5.36 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C4      ..       8.15 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C5      ..       7.19 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe2    -   C1      ..       8.07 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe2    -   C2      ..       9.25 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe2    -   C3      ..       5.73 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         78
            C4  -FE1 -C5  -O5    -11.00 15.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         79
            P   -FE1 -C5  -O5     87.00 15.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         80
            S1  -FE1 -C5  -O5     18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         81
            S2  -FE1 -C5  -O5   -101.00 15.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         82
            FE2 -FE1 -C5  -O5   -120.00 15.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         89
            C5  -FE1 -C4  -O4      4.00 20.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         90
            P   -FE1 -C4  -O4    -92.00 20.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         91
            S1  -FE1 -C4  -O4     97.00 20.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         92
            S2  -FE1 -C4  -O4    163.00 20.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         93
            FE2 -FE1 -C4  -O4    110.00 20.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         98
            C3  -FE2 -C1  -O1      1.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         99
            C2  -FE2 -C1  -O1     10.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        100
            S1  -FE2 -C1  -O1      8.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        101
            S2  -FE2 -C1  -O1     17.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        102
            FE1 -FE2 -C1  -O1     13.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        104
            C2  -FE2 -C3  -O3   -141.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        105
            C1  -FE2 -C3  -O3    115.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        106
            S1  -FE2 -C3  -O3     11.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        107
            S2  -FE2 -C3  -O3    -54.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        108
            FE1 -FE2 -C3  -O3    -43.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        112
            C3  -FE2 -C2  -O2     80.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        113
            C1  -FE2 -C2  -O2     18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        114
            S1  -FE2 -C2  -O2     -6.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        115
            S2  -FE2 -C2  -O2    -79.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        116
            FE1 -FE2 -C2  -O2    -24.00  6.00   1.555   1.555   1.555   1.555


Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe2         (3)       3.79


   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  40 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
  26 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check
Comment top

Iron hydrogenases (Fe—H2ase) are highly efficient enzymes that catalyze the reversible reduction of protons to molecular hydrogen. Crystallographic study revealed that the active site of Fe—H2ase is comprised of one unusual low-valent diiron disulfide that is linked by a cysteine-ligand to a [Fe4S4] cluster, with one bridging carbonyl and an additional terminal carbonyl, cyanide and aqua ligands and the non-proteic dithiolate (Nicolet et al., 2000; Frey, 2002). The molecule of the title compound, (I), (Fig. 1), exhibits some resemblance to the active site of Fe-hydrogenases.

The central 2Fe2S structure in compound I is in the butterfly conformation, with a dihedral angle of 108.4 (2)° between the two Fe2S planes, and each iron atom displays pseudo-square-pyramidal geometry. The Fe—Fe distance in (I) (2.5143 (6) Å) agrees well with those found in other similar complexes [2.49–2.51 Å; Lawrence et al., 2001; Liu et al., 2004; Wang et al., 2005, Gao et al., 2007]. The phosphine group occupies an apical position. The propyl group on the bridged nitrogen atom is in an equatorial position and the propyl chain takes the zigzag form.

As shown in the packing diagram (Fig. 2), adjacent pairs of molecules are associated by S···S(3.625 Å) intermolecular non-bonded weak interactions. The distance is close to the sum of the van der Waals radii for two sulfur atoms (3.6 Å).

Related literature top

For literature on 2Fe2S complexes, where the two Fe atoms are bridged by a dithiolate ligand and each of the Fe atoms coordinated by carbonyl groups or tertiary phosphine ligands, see Lawrence et al. (2001); Liu et al. (2004); Wang et al. (2005); Gao et al. (2007).

For related literature, see: Frey (2002); Milway et al. (2006); Nicolet et al. (2000).

Experimental top

(µ-SCH2)2NCH2CH2CH3[Fe2(CO)6] (0.10 g, 0.23 mmol) was dissolved in dry acetonitrile (15 ml) and Me3NO.2H2O (51 mg, 0.46 mmol) was added under an argon atmosphere. When the color of the solution turned dark red Diphenylphosphine (46 mg, 0.25 mmol) was added and the solution was stirred at 293 K for 1.5 h and the color turned to red. After the solvent was removed in vacuum, the crude product was purified by column chromatography on silica gel with CH2Cl2/hexane (1:1) as eluent to give I as red solid (109 mg, 81%). Single crystals of (I) for X-ray analysis were grown by slow diffusion of hexane into a solution of the complex in CH2Cl2 at 275 K.

Refinement top

H atoms bonded to P atoms were located geometrically and allowed to ride on its parent atoms with distance restraints of P—H = 1.32 (2) Å, and with Uiso(H) = 1.2Ueq(P). Other H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Structure description top

Iron hydrogenases (Fe—H2ase) are highly efficient enzymes that catalyze the reversible reduction of protons to molecular hydrogen. Crystallographic study revealed that the active site of Fe—H2ase is comprised of one unusual low-valent diiron disulfide that is linked by a cysteine-ligand to a [Fe4S4] cluster, with one bridging carbonyl and an additional terminal carbonyl, cyanide and aqua ligands and the non-proteic dithiolate (Nicolet et al., 2000; Frey, 2002). The molecule of the title compound, (I), (Fig. 1), exhibits some resemblance to the active site of Fe-hydrogenases.

The central 2Fe2S structure in compound I is in the butterfly conformation, with a dihedral angle of 108.4 (2)° between the two Fe2S planes, and each iron atom displays pseudo-square-pyramidal geometry. The Fe—Fe distance in (I) (2.5143 (6) Å) agrees well with those found in other similar complexes [2.49–2.51 Å; Lawrence et al., 2001; Liu et al., 2004; Wang et al., 2005, Gao et al., 2007]. The phosphine group occupies an apical position. The propyl group on the bridged nitrogen atom is in an equatorial position and the propyl chain takes the zigzag form.

As shown in the packing diagram (Fig. 2), adjacent pairs of molecules are associated by S···S(3.625 Å) intermolecular non-bonded weak interactions. The distance is close to the sum of the van der Waals radii for two sulfur atoms (3.6 Å).

For literature on 2Fe2S complexes, where the two Fe atoms are bridged by a dithiolate ligand and each of the Fe atoms coordinated by carbonyl groups or tertiary phosphine ligands, see Lawrence et al. (2001); Liu et al. (2004); Wang et al. (2005); Gao et al. (2007).

For related literature, see: Frey (2002); Milway et al. (2006); Nicolet et al. (2000).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis, showing S···S intermolecular weak interactions (dashed lines). H atoms have been omitted.
Pentacarbonyl-1κ2C,2κ3C-(diphenylphosphine-1κP)(µ-2-propyl-2- azapropane-1,3-dithiolato-1κ2S,S':2κ2S,S')diiron(Fe—Fe) top
Crystal data top
[Fe2(C5H11NS2)(C12H11P)(CO)5]F(000) = 1200
Mr = 587.20Dx = 1.487 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.4627 (15) ÅCell parameters from 3783 reflections
b = 12.1985 (15) Åθ = 2.4–23.4°
c = 17.2573 (2) ŵ = 1.36 mm−1
β = 90.162 (2)°T = 273 K
V = 2623.6 (6) Å3Block, red
Z = 40.30 × 0.20 × 0.08 mm
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		4885 independent reflections
Radiation source: fine-focus sealed tube3350 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→8
Tmin = 0.686, Tmax = 0.899k = −13→14
13194 measured reflectionsl = −20→20
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0429P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087(Δ/σ)max < 0.001
S = 0.92Δρmax = 0.44 e Å−3
4885 reflectionsΔρmin = −0.38 e Å−3
302 parameters
Crystal data top
[Fe2(C5H11NS2)(C12H11P)(CO)5]V = 2623.6 (6) Å3
Mr = 587.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.4627 (15) ŵ = 1.36 mm−1
b = 12.1985 (15) ÅT = 273 K
c = 17.2573 (2) Å0.30 × 0.20 × 0.08 mm
β = 90.162 (2)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		4885 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3350 reflections with I > 2σ(I)
Tmin = 0.686, Tmax = 0.899Rint = 0.041
13194 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 0.92Δρmax = 0.44 e Å−3
4885 reflectionsΔρmin = −0.38 e Å−3
302 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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.30424 (3)0.45814 (4)0.12088 (2)0.05683 (14)
Fe20.23171 (3)0.36249 (4)0.00279 (2)0.06549 (15)
P0.34731 (6)0.61660 (7)0.17360 (4)0.0584 (2)
S20.13569 (6)0.48156 (7)0.07511 (4)0.0643 (2)
S10.35457 (6)0.49763 (7)−0.00134 (4)0.0620 (2)
O50.51096 (19)0.3537 (2)0.14933 (14)0.0892 (7)
C110.2452 (2)0.7071 (3)0.21361 (15)0.0594 (7)
C170.4470 (2)0.6044 (2)0.25035 (16)0.0623 (8)
C50.4302 (3)0.3951 (3)0.13735 (16)0.0657 (8)
O40.2164 (2)0.3518 (2)0.25765 (14)0.1033 (8)
C70.2972 (2)0.6299 (2)−0.03031 (17)0.0698 (8)
H7A0.35530.6816−0.03810.084*
H7B0.26060.6207−0.07960.084*
C220.4207 (3)0.5575 (3)0.32002 (18)0.0893 (11)
H22A0.35020.53680.32940.107*
O10.1227 (2)0.3756 (2)−0.14763 (15)0.1042 (9)
N10.22289 (19)0.6757 (2)0.02462 (13)0.0661 (7)
C40.2501 (2)0.3940 (3)0.20373 (19)0.0713 (9)
O30.4083 (2)0.2168 (2)−0.04003 (16)0.1197 (10)
C120.1424 (2)0.6704 (3)0.22953 (17)0.0747 (9)
H12A0.12490.59730.22060.090*
C180.5521 (3)0.6346 (3)0.23811 (19)0.0735 (9)
H18A0.57160.66660.19130.088*
C10.1643 (3)0.3708 (3)−0.0897 (2)0.0764 (9)
C190.6285 (3)0.6179 (3)0.2949 (2)0.0903 (11)
H19A0.69910.63910.28590.108*
C140.0908 (3)0.8476 (4)0.2707 (2)0.0965 (12)
H14A0.03880.89520.28970.116*
C90.1694 (4)0.8407 (4)−0.0525 (2)0.1237 (15)
H9A0.09870.8103−0.06210.148*
H9B0.21570.8199−0.09510.148*
O20.1204 (2)0.1872 (2)0.08541 (18)0.1176 (10)
C30.3380 (3)0.2727 (3)−0.02344 (18)0.0809 (10)
C200.6026 (4)0.5713 (3)0.3630 (3)0.1004 (12)
H20A0.65500.55990.40060.120*
C160.2692 (3)0.8157 (3)0.22726 (17)0.0743 (9)
H16A0.33800.84170.21740.089*
C20.1618 (3)0.2550 (3)0.0515 (2)0.0834 (10)
C130.0657 (3)0.7404 (4)0.25838 (19)0.0878 (11)
H13A−0.00280.71470.26940.105*
C60.1233 (2)0.6155 (3)0.02812 (18)0.0723 (9)
H6A0.09640.6050−0.02420.087*
H6B0.07090.65890.05610.087*
C100.1619 (5)0.9682 (4)−0.0479 (3)0.153 (2)
H10A0.13340.9962−0.09570.229*
H10B0.23220.9982−0.03920.229*
H10C0.11560.9887−0.00600.229*
C210.4982 (4)0.5408 (4)0.3766 (2)0.1135 (14)
H21A0.47960.50890.42370.136*
H10.3993 (18)0.6872 (19)0.1294 (13)0.061 (7)*
C150.1918 (3)0.8861 (3)0.2554 (2)0.0918 (11)
H15A0.20830.95950.26400.110*
C80.2117 (3)0.7970 (3)0.0188 (2)0.0990 (12)
H8A0.16570.82120.06070.119*
H8B0.28180.82920.02750.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0436 (2)0.0801 (3)0.0468 (2)−0.00482 (19)0.00266 (17)−0.0036 (2)
Fe20.0520 (3)0.0888 (4)0.0557 (3)−0.0045 (2)0.0037 (2)−0.0147 (2)
P0.0474 (4)0.0806 (6)0.0472 (4)−0.0090 (4)0.0007 (3)−0.0009 (4)
S20.0407 (4)0.0926 (6)0.0597 (4)−0.0059 (4)0.0050 (3)−0.0133 (4)
S10.0424 (4)0.0942 (6)0.0496 (4)0.0001 (4)0.0043 (3)−0.0024 (4)
O50.0612 (15)0.118 (2)0.0883 (16)0.0159 (13)0.0021 (13)0.0201 (13)
C110.0552 (19)0.079 (2)0.0445 (15)−0.0028 (15)−0.0037 (13)−0.0057 (14)
C170.0560 (18)0.075 (2)0.0556 (17)−0.0081 (15)−0.0063 (14)−0.0049 (15)
C50.060 (2)0.085 (2)0.0525 (16)−0.0046 (17)0.0073 (15)0.0067 (16)
O40.108 (2)0.122 (2)0.0805 (16)−0.0190 (15)0.0295 (15)0.0187 (14)
C70.0607 (19)0.092 (2)0.0566 (17)0.0015 (16)0.0021 (15)0.0050 (16)
C220.076 (2)0.132 (3)0.060 (2)−0.023 (2)−0.0126 (18)0.005 (2)
O10.101 (2)0.140 (2)0.0720 (16)−0.0120 (15)−0.0218 (15)−0.0162 (15)
N10.0534 (15)0.0848 (19)0.0602 (15)0.0054 (13)0.0046 (12)−0.0012 (13)
C40.061 (2)0.087 (2)0.066 (2)−0.0055 (17)0.0042 (17)−0.0049 (18)
O30.114 (2)0.118 (2)0.128 (2)0.0364 (18)0.0429 (19)0.0009 (18)
C120.064 (2)0.098 (3)0.0629 (19)−0.0093 (18)0.0071 (16)−0.0216 (17)
C180.057 (2)0.089 (2)0.074 (2)−0.0034 (16)−0.0104 (17)−0.0060 (17)
C10.060 (2)0.097 (3)0.073 (2)−0.0115 (17)0.0076 (18)−0.0206 (19)
C190.064 (2)0.096 (3)0.111 (3)0.0000 (19)−0.021 (2)−0.017 (2)
C140.083 (3)0.132 (4)0.075 (2)0.026 (3)−0.002 (2)−0.027 (2)
C90.137 (4)0.148 (5)0.087 (3)0.016 (3)−0.010 (3)−0.003 (3)
O20.118 (2)0.103 (2)0.131 (2)−0.0263 (18)0.0403 (19)−0.0058 (18)
C30.081 (3)0.093 (3)0.069 (2)−0.001 (2)0.0114 (19)−0.0051 (18)
C200.098 (3)0.105 (3)0.098 (3)0.005 (3)−0.046 (3)−0.008 (2)
C160.070 (2)0.086 (3)0.067 (2)−0.0087 (19)−0.0003 (17)−0.0069 (18)
C20.069 (2)0.099 (3)0.082 (2)−0.002 (2)0.0084 (19)−0.025 (2)
C130.059 (2)0.126 (3)0.078 (2)−0.001 (2)0.0031 (17)−0.034 (2)
C60.0519 (19)0.095 (2)0.070 (2)0.0088 (17)−0.0029 (15)−0.0055 (17)
C100.226 (6)0.091 (4)0.141 (4)0.044 (3)0.021 (4)0.007 (3)
C210.138 (4)0.133 (4)0.070 (2)−0.024 (3)−0.032 (3)0.018 (2)
C150.105 (3)0.084 (3)0.086 (3)0.004 (2)0.005 (2)−0.013 (2)
C80.102 (3)0.111 (3)0.084 (3)0.024 (2)0.003 (2)0.004 (2)
Geometric parameters (Å, º) top
Fe1—C41.766 (3)O3—C31.148 (4)
Fe1—C51.770 (3)C12—C131.376 (4)
Fe1—P2.2021 (9)C12—H12A0.9300
Fe1—S12.2543 (8)C18—C191.380 (4)
Fe1—S22.2603 (9)C18—H18A0.9300
Fe1—Fe22.5143 (6)C19—C201.345 (5)
Fe2—C31.778 (4)C19—H19A0.9300
Fe2—C21.786 (4)C14—C131.361 (5)
Fe2—C11.805 (4)C14—C151.370 (5)
Fe2—S12.2512 (9)C14—H14A0.9300
Fe2—S22.2602 (9)C9—C81.439 (5)
P—C171.820 (3)C9—C101.561 (5)
P—C111.821 (3)C9—H9A0.9700
P—H11.32 (2)C9—H9B0.9700
S2—C61.831 (3)O2—C21.138 (4)
S1—C71.833 (3)C20—C211.374 (5)
O5—C51.145 (3)C20—H20A0.9300
C11—C161.378 (4)C16—C151.381 (4)
C11—C121.386 (4)C16—H16A0.9300
C17—C221.372 (4)C13—H13A0.9300
C17—C181.377 (4)C6—H6A0.9700
O4—C41.144 (3)C6—H6B0.9700
C7—N11.440 (3)C10—H10A0.9600
C7—H7A0.9700C10—H10B0.9600
C7—H7B0.9700C10—H10C0.9600
C22—C211.387 (5)C21—H21A0.9300
C22—H22A0.9300C15—H15A0.9300
O1—C11.126 (4)C8—H8A0.9700
N1—C61.444 (4)C8—H8B0.9700
N1—C81.490 (4)
C4—Fe1—C591.03 (13)C7—N1—C6112.7 (2)
C4—Fe1—P98.50 (11)C7—N1—C8113.7 (2)
C5—Fe1—P95.76 (11)C6—N1—C8115.3 (3)
C4—Fe1—S1163.81 (11)O4—C4—Fe1179.0 (3)
C5—Fe1—S189.67 (9)C13—C12—C11121.0 (3)
P—Fe1—S197.52 (3)C13—C12—H12A119.5
C4—Fe1—S288.97 (10)C11—C12—H12A119.5
C5—Fe1—S2159.03 (11)C17—C18—C19120.4 (3)
P—Fe1—S2104.99 (3)C17—C18—H18A119.8
S1—Fe1—S284.65 (3)C19—C18—H18A119.8
C4—Fe1—Fe2108.26 (10)O1—C1—Fe2179.5 (3)
C5—Fe1—Fe2104.18 (10)C20—C19—C18121.1 (4)
P—Fe1—Fe2145.99 (3)C20—C19—H19A119.5
S1—Fe1—Fe256.02 (2)C18—C19—H19A119.5
S2—Fe1—Fe256.20 (2)C13—C14—C15120.7 (3)
C3—Fe2—C291.87 (16)C13—C14—H14A119.7
C3—Fe2—C198.92 (15)C15—C14—H14A119.7
C2—Fe2—C1103.33 (15)C8—C9—C10110.4 (4)
C3—Fe2—S186.31 (12)C8—C9—H9A109.6
C2—Fe2—S1152.32 (11)C10—C9—H9A109.6
C1—Fe2—S1104.24 (11)C8—C9—H9B109.6
C3—Fe2—S2158.79 (11)C10—C9—H9B109.6
C2—Fe2—S287.26 (11)H9A—C9—H9B108.1
C1—Fe2—S2101.90 (11)O3—C3—Fe2178.4 (4)
S1—Fe2—S284.73 (3)C19—C20—C21119.5 (4)
C3—Fe2—Fe1103.04 (11)C19—C20—H20A120.2
C2—Fe2—Fe197.72 (11)C21—C20—H20A120.2
C1—Fe2—Fe1148.90 (11)C11—C16—C15120.5 (3)
S1—Fe2—Fe156.14 (2)C11—C16—H16A119.8
S2—Fe2—Fe156.21 (2)C15—C16—H16A119.8
C17—P—C11104.48 (13)O2—C2—Fe2176.7 (4)
C17—P—Fe1113.19 (10)C14—C13—C12119.6 (3)
C11—P—Fe1121.25 (10)C14—C13—H13A120.2
C17—P—H198.0 (10)C12—C13—H13A120.2
C11—P—H199.6 (10)N1—C6—S2113.6 (2)
Fe1—P—H1117.0 (10)N1—C6—H6A108.8
C6—S2—Fe2111.91 (10)S2—C6—H6A108.8
C6—S2—Fe1110.18 (10)N1—C6—H6B108.8
Fe2—S2—Fe167.59 (3)S2—C6—H6B108.8
C7—S1—Fe2112.84 (10)H6A—C6—H6B107.7
C7—S1—Fe1109.50 (10)C9—C10—H10A109.5
Fe2—S1—Fe167.84 (3)C9—C10—H10B109.5
C16—C11—C12118.5 (3)H10A—C10—H10B109.5
C16—C11—P119.7 (2)C9—C10—H10C109.5
C12—C11—P121.8 (2)H10A—C10—H10C109.5
C22—C17—C18118.4 (3)H10B—C10—H10C109.5
C22—C17—P120.5 (2)C20—C21—C22119.8 (4)
C18—C17—P120.9 (2)C20—C21—H21A120.1
O5—C5—Fe1178.7 (3)C22—C21—H21A120.1
N1—C7—S1114.4 (2)C14—C15—C16119.8 (4)
N1—C7—H7A108.7C14—C15—H15A120.1
S1—C7—H7A108.7C16—C15—H15A120.1
N1—C7—H7B108.7C9—C8—N1117.4 (3)
S1—C7—H7B108.7C9—C8—H8A108.0
H7A—C7—H7B107.6N1—C8—H8A108.0
C17—C22—C21120.8 (3)C9—C8—H8B108.0
C17—C22—H22A119.6N1—C8—H8B108.0
C21—C22—H22A119.6H8A—C8—H8B107.2
C4—Fe1—Fe2—C3−99.28 (16)C4—Fe1—S1—Fe214.9 (4)
C5—Fe1—Fe2—C3−3.37 (15)C5—Fe1—S1—Fe2107.42 (10)
P—Fe1—Fe2—C3120.64 (12)P—Fe1—S1—Fe2−156.82 (3)
S1—Fe1—Fe2—C376.41 (12)S2—Fe1—S1—Fe2−52.37 (3)
S2—Fe1—Fe2—C3−175.18 (12)C17—P—C11—C1667.9 (3)
C4—Fe1—Fe2—C2−5.54 (16)Fe1—P—C11—C16−162.90 (19)
C5—Fe1—Fe2—C290.36 (15)C17—P—C11—C12−113.5 (3)
P—Fe1—Fe2—C2−145.63 (12)Fe1—P—C11—C1215.8 (3)
S1—Fe1—Fe2—C2170.14 (12)C11—P—C17—C2263.2 (3)
S2—Fe1—Fe2—C2−81.44 (12)Fe1—P—C17—C22−70.7 (3)
C4—Fe1—Fe2—C1126.9 (2)C11—P—C17—C18−121.4 (3)
C5—Fe1—Fe2—C1−137.2 (2)Fe1—P—C17—C18104.7 (2)
P—Fe1—Fe2—C1−13.2 (2)C4—Fe1—C5—O5−11 (15)
S1—Fe1—Fe2—C1−57.39 (19)P—Fe1—C5—O587 (15)
S2—Fe1—Fe2—C151.03 (19)S1—Fe1—C5—O5−175 (100)
C4—Fe1—Fe2—S1−175.68 (11)S2—Fe1—C5—O5−101 (15)
C5—Fe1—Fe2—S1−79.78 (10)Fe2—Fe1—C5—O5−120 (15)
P—Fe1—Fe2—S144.23 (5)Fe2—S1—C7—N166.4 (2)
S2—Fe1—Fe2—S1108.41 (4)Fe1—S1—C7—N1−7.0 (2)
C4—Fe1—Fe2—S275.90 (11)C18—C17—C22—C21−0.2 (5)
C5—Fe1—Fe2—S2171.81 (10)P—C17—C22—C21175.3 (3)
P—Fe1—Fe2—S2−64.18 (5)S1—C7—N1—C6−70.3 (3)
S1—Fe1—Fe2—S2−108.41 (4)S1—C7—N1—C8156.2 (2)
C4—Fe1—P—C1762.32 (15)C5—Fe1—C4—O44 (20)
C5—Fe1—P—C17−29.59 (14)P—Fe1—C4—O4−92 (20)
S1—Fe1—P—C17−120.01 (11)S1—Fe1—C4—O497 (20)
S2—Fe1—P—C17153.54 (11)S2—Fe1—C4—O4163 (20)
Fe2—Fe1—P—C17−155.71 (11)Fe2—Fe1—C4—O4110 (20)
C4—Fe1—P—C11−62.99 (15)C16—C11—C12—C13−0.1 (5)
C5—Fe1—P—C11−154.90 (14)P—C11—C12—C13−178.8 (2)
S1—Fe1—P—C11114.67 (11)C22—C17—C18—C190.0 (5)
S2—Fe1—P—C1128.22 (11)P—C17—C18—C19−175.5 (2)
Fe2—Fe1—P—C1178.98 (12)C3—Fe2—C1—O1−5 (51)
C3—Fe2—S2—C6116.7 (3)C2—Fe2—C1—O1−99 (51)
C2—Fe2—S2—C6−155.14 (16)S1—Fe2—C1—O184 (51)
C1—Fe2—S2—C6−52.10 (15)S2—Fe2—C1—O1171 (100)
S1—Fe2—S2—C651.37 (11)Fe1—Fe2—C1—O1130 (51)
Fe1—Fe2—S2—C6103.67 (11)C17—C18—C19—C200.4 (5)
C3—Fe2—S2—Fe113.1 (3)C2—Fe2—C3—O3−141 (12)
C2—Fe2—S2—Fe1101.18 (12)C1—Fe2—C3—O3115 (12)
C1—Fe2—S2—Fe1−155.77 (11)S1—Fe2—C3—O311 (12)
S1—Fe2—S2—Fe1−52.30 (3)S2—Fe2—C3—O3−54 (12)
C4—Fe1—S2—C6140.93 (15)Fe1—Fe2—C3—O3−43 (12)
C5—Fe1—S2—C6−128.9 (3)C18—C19—C20—C21−0.5 (6)
P—Fe1—S2—C642.41 (11)C12—C11—C16—C15−0.6 (4)
S1—Fe1—S2—C6−53.97 (11)P—C11—C16—C15178.1 (2)
Fe2—Fe1—S2—C6−106.17 (11)C3—Fe2—C2—O280 (6)
C4—Fe1—S2—Fe2−112.90 (11)C1—Fe2—C2—O2179 (100)
C5—Fe1—S2—Fe2−22.7 (3)S1—Fe2—C2—O2−6 (6)
P—Fe1—S2—Fe2148.58 (3)S2—Fe2—C2—O2−79 (6)
S1—Fe1—S2—Fe252.21 (3)Fe1—Fe2—C2—O2−24 (6)
C3—Fe2—S1—C7148.92 (15)C15—C14—C13—C12−0.7 (6)
C2—Fe2—S1—C7−124.1 (3)C11—C12—C13—C140.7 (5)
C1—Fe2—S1—C750.64 (15)C7—N1—C6—S271.9 (3)
S2—Fe2—S1—C7−50.33 (10)C8—N1—C6—S2−155.4 (2)
Fe1—Fe2—S1—C7−102.69 (11)Fe2—S2—C6—N1−69.1 (2)
C3—Fe2—S1—Fe1−108.40 (11)Fe1—S2—C6—N14.0 (2)
C2—Fe2—S1—Fe1−21.4 (2)C19—C20—C21—C220.3 (7)
C1—Fe2—S1—Fe1153.33 (11)C17—C22—C21—C200.1 (6)
S2—Fe2—S1—Fe152.36 (3)C13—C14—C15—C160.0 (6)
C4—Fe1—S1—C7122.3 (4)C11—C16—C15—C140.7 (5)
C5—Fe1—S1—C7−145.10 (15)C10—C9—C8—N1179.3 (3)
P—Fe1—S1—C7−49.34 (11)C7—N1—C8—C963.0 (4)
S2—Fe1—S1—C755.12 (11)C6—N1—C8—C9−69.2 (4)
Fe2—Fe1—S1—C7107.48 (11)

Experimental details

Crystal data
Chemical formula[Fe2(C5H11NS2)(C12H11P)(CO)5]
Mr587.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)12.4627 (15), 12.1985 (15), 17.2573 (2)
β (°) 90.162 (2)
V (Å3)2623.6 (6)
Z4
Radiation typeMo Kα
µ (mm−1)1.36
Crystal size (mm)0.30 × 0.20 × 0.08
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.686, 0.899
No. of measured, independent and
observed [I > 2σ(I)] reflections		13194, 4885, 3350
Rint0.041
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.087, 0.92
No. of reflections4885
No. of parameters302
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.44, −0.38

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

Selected geometric parameters (Å, º) top
Fe1—P2.2021 (9)P—H11.32 (2)
Fe1—Fe22.5143 (6)
P—Fe1—Fe2145.99 (3)C7—N1—C8113.7 (2)
C7—N1—C6112.7 (2)C6—N1—C8115.3 (3)
 

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