Dicarbon­yl(η5-cyclo­penta­dien­yl)[2-(phenyl­sulfan­yl)eth­yl]iron(II)

Mkhize, D.S.; Nyamori, V.O.; Bala, M.D.

doi:10.1107/S160053681101511X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m644

doi:10.1107/S160053681101511X

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Dicarbonyl(η⁵-cyclopentadienyl)[2-(phenylsulfanyl)ethyl]iron(II)

Dennis S. Mkhize,^a Vincent O. Nyamori ^a and Muhammad D. Bala ^a ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: bala@ukzn.ac.za

(Received 11 April 2011; accepted 21 April 2011; online 29 April 2011)

The title compound, [Fe(C₅H₅)(C₈H₉S)(CO)₂], is a three-legged piano-stool iron(II) complex that is characterized by a thioethyl-linked phenyl ring and a cyclopentadienyl moiety that occupies the apical coordination site. The two aromatic rings are essentially planar with the same maximum deviation of 0.009 Å. The mean planes of the phenyl and cyclopentadienyl rings bisect at an acute angle of 50.08°.

Related literature

For general background and related synthesis, see: King & Bisnette (1965a ,b ); Theys et al. (2009 ); Nyamori et al. (2008 ). For related structures, see: O'Connor et al. (1987 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₈H₉S)(CO)₂]
M_r = 314.17
Orthorhombic, P b c a
a = 10.3992 (5) Å
b = 7.6402 (4) Å
c = 35.4173 (16) Å
V = 2814.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 173 K
0.57 × 0.27 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration (SADABS; Bruker, 2009 ) T_min = 0.545, T_max = 0.909
20490 measured reflections
2752 independent reflections
2339 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.153
S = 1.26
2752 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101511X/dn2676sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101511X/dn2676Isup2.hkl

checkCIF report

Comment top

Organosulfur compounds of iron are valuable compounds that are used for the synthesis of organometallic catalysts and catalysts precursor salts. Amongst many applications this salts have been used for the cyclopropanation of alkenes (O'Connor et al., 1987). The recent proliferation and interest in the chemistry of materials has also rekindled interest in Fe-based organometallics as catalysts for the synthesis of carbon nanotubes and nanomaterials in general (Nyamori et al., 2008).

We are currently studying the application of (I) as a precursor catalyst in the synthesis of carbon nanomaterials. The presence of sulfur in this compound was believed to play the role of increasing the yield and affecting the morphology of the products obtained. In the title compound (I), the coordination of ligands around the Fe(II) ion is described as three-legged piano stool distorted octahedral geometry (Fig. 1). This is a typical geometry for complexes based on the dicarbonyl(η⁵-cyclopentadienyl)Fe(II) moiety (generally abbreviated as the Fp anion) and many compounds of iron with this geometry are well documented (Theys, et al., 2009; O'Connor et al., 1987).

Related literature top

For general background and related synthesis, see: King & Bisnette (1965a,b); Theys, et al. (2009); Nyamori et al. (2008). For related structures, see: O'Connor et al. (1987).

Experimental top

A solution of cyclopentadienylirondicarbonyl dimer (1.501 g, 0.424 mmol) in dry tetrahydrofuran was treated with Na/Hg amalgam [sodium (0.2902 g, 12.70 mmol) and mercury (2.8 ml, 18.75 mmol)] and stirred at room temperature for two hours. The resulting yellowish-brown solution was transferred into another flask via a cannula and reacted with 2-chloroethyl phenyl sulfide (0.729 g, 4.242 mmol). The reaction mixture was allowed to stir for 16 h at room temperature. After concentrating the greyish brown mixture in vacuo it was extracted with dichloromethane (3 × 30 ml). Filtration of the extracted product through a celite pad afforded a clear brownish-orange filtrate which was further reduced in vacuo. The brown oil that resulted was purified by flash collumn chromatography on silica using hexane as mobile phase. A dark yellow band was collected and removal of volatiles afforded 0.8183 g of the final product as a yellow crystalline solid (yield, 61%).

¹H NMR δ_H (400 MHz, CDCl₃, p.p.m.): 1.58 (2H, t, J 8.56, CH₂), 3.02 (2H, t, J 8.40, CH₂), 4.68 (5H, s, Cp), 7.08 (1H, t, ArH), 7.20 (2H, m, J16.4, ArH₂), 7.26 (2H, m, J 16.5, ArH₂).

¹³C NMR (400 MHz, CDCl₃, p.p.m.): 40.72, 84.03, 124.3, 127.6, 127.8, 136.1, 215.6.

IR (ν_CO, cm^-1): 1993, 1937, 1708.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 (Bruker, 2009); data reduction: APEX2 (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2009).

Figures top

Fig. 1. Molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radii.

Dicarbonyl(η⁵-cyclopentadienyl)[2-(phenylsulfanyl)ethyl]iron(II) top

Crystal data top

[Fe(C₅H₅)(C₈H₉S)(CO)₂]	F(000) = 1296
M_r = 314.17	D_x = 1.483 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6363 reflections
a = 10.3992 (5) Å	θ = 2.3–27.3°
b = 7.6402 (4) Å	µ = 1.21 mm⁻¹
c = 35.4173 (16) Å	T = 173 K
V = 2814.0 (2) Å³	Plate, yellow
Z = 8	0.57 × 0.27 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2752 independent reflections
Radiation source: fine-focus sealed tube	2339 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: integration (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.545, T_max = 0.909	k = −9→9
20490 measured reflections	l = −41→43

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.26	w = 1/[σ²(F_o²) + (0.P)² + 19.462P] where P = (F_o² + 2F_c²)/3
2752 reflections	(Δ/σ)_max = 0.004
172 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₈H₉S)(CO)₂]	V = 2814.0 (2) Å³
M_r = 314.17	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.3992 (5) Å	µ = 1.21 mm⁻¹
b = 7.6402 (4) Å	T = 173 K
c = 35.4173 (16) Å	0.57 × 0.27 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2752 independent reflections
Absorption correction: integration (SADABS; Bruker, 2009)	2339 reflections with I > 2σ(I)
T_min = 0.545, T_max = 0.909	R_int = 0.068
20490 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.26	w = 1/[σ²(F_o²) + (0.P)² + 19.462P] where P = (F_o² + 2F_c²)/3
2752 reflections	Δρ_max = 0.49 e Å⁻³
172 parameters	Δρ_min = −0.75 e Å⁻³

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

	x	y	z	U_iso*/U_eq
C1	0.5039 (8)	0.7838 (8)	0.40483 (18)	0.0425 (17)
H1	0.4331	0.8509	0.3961	0.051*
C2	0.5565 (8)	0.7851 (9)	0.44168 (19)	0.0459 (19)
H2	0.5266	0.8551	0.4620	0.055*
C3	0.6571 (7)	0.6697 (10)	0.4435 (2)	0.0461 (18)
H3	0.7090	0.6465	0.4650	0.055*
C4	0.6699 (7)	0.5910 (9)	0.4073 (2)	0.0430 (17)
H4	0.7308	0.5040	0.4004	0.052*
C5	0.5767 (7)	0.6644 (7)	0.38373 (17)	0.0348 (15)
H5	0.5648	0.6379	0.3578	0.042*
C6	0.5240 (6)	0.3405 (8)	0.45376 (15)	0.0279 (13)
C7	0.3395 (7)	0.5626 (8)	0.45266 (17)	0.0366 (15)
C8	0.3943 (6)	0.3817 (8)	0.39055 (16)	0.0333 (14)
H8A	0.3294	0.3098	0.4039	0.040*
H8B	0.3476	0.4590	0.3728	0.040*
C9	0.4800 (6)	0.2613 (8)	0.36798 (16)	0.0327 (14)
H9A	0.5282	0.1825	0.3851	0.039*
H9B	0.5424	0.3302	0.3530	0.039*
C10	0.4778 (7)	−0.0152 (8)	0.31408 (16)	0.0377 (15)
C11	0.6121 (7)	−0.0106 (7)	0.31470 (16)	0.0357 (15)
H11	0.6553	0.0756	0.3293	0.043*
C12	0.6823 (7)	−0.1315 (9)	0.29414 (17)	0.0392 (16)
H12	0.7736	−0.1261	0.2943	0.047*
C13	0.6207 (8)	−0.2602 (9)	0.27334 (18)	0.0471 (19)
H13	0.6691	−0.3431	0.2593	0.056*
C14	0.4893 (9)	−0.2665 (10)	0.27328 (18)	0.053 (2)
H14	0.4468	−0.3551	0.2592	0.063*
C15	0.4172 (8)	−0.1468 (9)	0.29330 (17)	0.0453 (18)
H15	0.3260	−0.1538	0.2930	0.054*
Fe1	0.48739 (8)	0.53522 (10)	0.42952 (2)	0.0264 (2)
O1	0.5463 (4)	0.2142 (5)	0.46915 (12)	0.0375 (11)
O2	0.2434 (5)	0.5784 (7)	0.46790 (14)	0.0558 (14)
S1	0.37701 (18)	0.1351 (2)	0.33694 (5)	0.0407 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.059 (5)	0.025 (3)	0.043 (4)	−0.004 (3)	0.005 (4)	0.014 (3)
C2	0.066 (5)	0.035 (4)	0.037 (4)	−0.024 (4)	0.015 (3)	0.002 (3)
C3	0.043 (4)	0.050 (4)	0.045 (4)	−0.022 (4)	−0.010 (3)	0.017 (3)
C4	0.034 (4)	0.039 (4)	0.055 (4)	−0.002 (3)	0.012 (3)	0.018 (3)
C5	0.052 (4)	0.025 (3)	0.028 (3)	−0.008 (3)	0.008 (3)	0.006 (2)
C6	0.026 (3)	0.033 (3)	0.025 (3)	0.003 (3)	0.000 (2)	0.000 (2)
C7	0.046 (4)	0.033 (3)	0.031 (3)	0.004 (3)	−0.001 (3)	0.003 (3)
C8	0.035 (4)	0.032 (3)	0.034 (3)	−0.005 (3)	−0.003 (3)	0.006 (3)
C9	0.041 (4)	0.027 (3)	0.031 (3)	−0.006 (3)	0.001 (3)	−0.002 (2)
C10	0.058 (5)	0.033 (3)	0.022 (3)	−0.011 (3)	−0.008 (3)	0.006 (2)
C11	0.058 (4)	0.020 (3)	0.030 (3)	−0.002 (3)	−0.004 (3)	0.004 (2)
C12	0.049 (4)	0.036 (3)	0.033 (3)	0.002 (3)	0.003 (3)	0.008 (3)
C13	0.078 (6)	0.031 (3)	0.033 (4)	0.003 (4)	0.003 (4)	0.001 (3)
C14	0.079 (6)	0.047 (4)	0.033 (3)	−0.016 (4)	−0.002 (4)	−0.010 (3)
C15	0.061 (5)	0.042 (4)	0.032 (3)	−0.014 (4)	−0.009 (3)	0.003 (3)
Fe1	0.0295 (5)	0.0238 (4)	0.0259 (4)	−0.0012 (4)	0.0019 (4)	0.0043 (3)
O1	0.043 (3)	0.030 (2)	0.040 (2)	0.001 (2)	0.001 (2)	0.007 (2)
O2	0.044 (3)	0.063 (4)	0.060 (3)	0.009 (3)	0.016 (3)	0.006 (3)
S1	0.0453 (11)	0.0401 (9)	0.0367 (8)	−0.0059 (8)	−0.0100 (8)	−0.0045 (7)

Geometric parameters (Å, º) top

C1—C5	1.401 (9)	C8—C9	1.510 (8)
C1—C2	1.415 (9)	C8—Fe1	2.054 (6)
C1—Fe1	2.098 (6)	C8—H8A	0.9900
C1—H1	0.9489	C8—H8B	0.9900
C2—C3	1.370 (11)	C9—S1	1.812 (6)
C2—Fe1	2.085 (6)	C9—H9A	0.9900
C2—H2	0.9490	C9—H9B	0.9900
C3—C4	1.422 (10)	C10—C15	1.396 (9)
C3—Fe1	2.101 (7)	C10—C11	1.397 (10)
C3—H3	0.9500	C10—S1	1.753 (7)
C4—C5	1.396 (9)	C11—C12	1.384 (9)
C4—Fe1	2.098 (7)	C11—H11	0.9500
C4—H4	0.9501	C12—C13	1.386 (9)
C5—Fe1	2.114 (6)	C12—H12	0.9500
C5—H5	0.9485	C13—C14	1.367 (11)
C6—O1	1.132 (7)	C13—H13	0.9500
C6—Fe1	1.759 (6)	C14—C15	1.379 (10)
C7—O2	1.142 (8)	C14—H14	0.9500
C7—Fe1	1.755 (7)	C15—H15	0.9500

C5—C1—C2	106.7 (6)	C11—C10—S1	125.1 (5)
C5—C1—Fe1	71.2 (3)	C12—C11—C10	120.2 (6)
C2—C1—Fe1	69.7 (4)	C12—C11—H11	119.9
C5—C1—H1	126.7	C10—C11—H11	119.9
C2—C1—H1	126.6	C11—C12—C13	120.6 (7)
Fe1—C1—H1	124.1	C11—C12—H12	119.7
C3—C2—C1	109.5 (7)	C13—C12—H12	119.7
C3—C2—Fe1	71.5 (4)	C14—C13—C12	119.2 (7)
C1—C2—Fe1	70.7 (4)	C14—C13—H13	120.4
C3—C2—H2	125.3	C12—C13—H13	120.4
C1—C2—H2	125.2	C13—C14—C15	121.3 (7)
Fe1—C2—H2	124.0	C13—C14—H14	119.4
C2—C3—C4	107.5 (6)	C15—C14—H14	119.4
C2—C3—Fe1	70.3 (4)	C14—C15—C10	120.2 (7)
C4—C3—Fe1	70.1 (4)	C14—C15—H15	119.9
C2—C3—H3	126.3	C10—C15—H15	119.9
C4—C3—H3	126.2	C7—Fe1—C6	93.6 (3)
Fe1—C3—H3	125.1	C7—Fe1—C8	88.2 (3)
C5—C4—C3	107.7 (6)	C6—Fe1—C8	87.0 (3)
C5—C4—Fe1	71.2 (4)	C7—Fe1—C2	95.5 (3)
C3—C4—Fe1	70.3 (4)	C6—Fe1—C2	126.8 (3)
C5—C4—H4	126.1	C8—Fe1—C2	145.5 (3)
C3—C4—H4	126.2	C7—Fe1—C4	160.7 (3)
Fe1—C4—H4	123.9	C6—Fe1—C4	99.1 (3)
C4—C5—C1	108.5 (6)	C8—Fe1—C4	106.9 (3)
C4—C5—Fe1	70.0 (3)	C2—Fe1—C4	65.2 (3)
C1—C5—Fe1	70.0 (3)	C7—Fe1—C1	99.1 (3)
C4—C5—H5	125.7	C6—Fe1—C1	162.0 (3)
C1—C5—H5	125.8	C8—Fe1—C1	106.0 (3)
Fe1—C5—H5	125.9	C2—Fe1—C1	39.6 (3)
O1—C6—Fe1	179.2 (6)	C4—Fe1—C1	65.5 (3)
O2—C7—Fe1	179.2 (6)	C7—Fe1—C3	124.6 (3)
C9—C8—Fe1	115.2 (4)	C6—Fe1—C3	96.7 (3)
C9—C8—H8A	108.5	C8—Fe1—C3	146.4 (3)
Fe1—C8—H8A	108.5	C2—Fe1—C3	38.2 (3)
C9—C8—H8B	108.5	C4—Fe1—C3	39.6 (3)
Fe1—C8—H8B	108.5	C1—Fe1—C3	65.6 (3)
H8A—C8—H8B	107.5	C7—Fe1—C5	133.5 (3)
C8—C9—S1	107.3 (4)	C6—Fe1—C5	132.4 (3)
C8—C9—H9A	110.3	C8—Fe1—C5	87.6 (2)
S1—C9—H9A	110.3	C2—Fe1—C5	65.1 (2)
C8—C9—H9B	110.3	C4—Fe1—C5	38.7 (3)
S1—C9—H9B	110.3	C1—Fe1—C5	38.9 (2)
H9A—C9—H9B	108.5	C3—Fe1—C5	65.4 (3)
C15—C10—C11	118.5 (7)	C10—S1—C9	106.0 (3)
C15—C10—S1	116.4 (6)

C5—C1—C2—C3	−0.6 (7)	C5—C4—Fe1—C8	63.4 (4)
Fe1—C1—C2—C3	61.4 (5)	C3—C4—Fe1—C8	−179.1 (4)
C5—C1—C2—Fe1	−62.0 (4)	C5—C4—Fe1—C2	−80.6 (4)
C1—C2—C3—C4	−0.4 (7)	C3—C4—Fe1—C2	37.0 (4)
Fe1—C2—C3—C4	60.5 (4)	C5—C4—Fe1—C1	−36.9 (4)
C1—C2—C3—Fe1	−60.8 (5)	C3—C4—Fe1—C1	80.7 (4)
C2—C3—C4—C5	1.2 (7)	C5—C4—Fe1—C3	−117.6 (6)
Fe1—C3—C4—C5	61.8 (4)	C3—C4—Fe1—C5	117.6 (6)
C2—C3—C4—Fe1	−60.6 (5)	C5—C1—Fe1—C7	−155.6 (4)
C3—C4—C5—C1	−1.6 (7)	C2—C1—Fe1—C7	87.6 (5)
Fe1—C4—C5—C1	59.6 (4)	C5—C1—Fe1—C6	69.9 (9)
C3—C4—C5—Fe1	−61.2 (4)	C2—C1—Fe1—C6	−46.9 (10)
C2—C1—C5—C4	1.4 (7)	C5—C1—Fe1—C8	−64.9 (5)
Fe1—C1—C5—C4	−59.6 (4)	C2—C1—Fe1—C8	178.4 (4)
C2—C1—C5—Fe1	61.0 (4)	C5—C1—Fe1—C2	116.7 (6)
Fe1—C8—C9—S1	178.1 (3)	C5—C1—Fe1—C4	36.8 (4)
C15—C10—C11—C12	1.9 (9)	C2—C1—Fe1—C4	−80.0 (5)
S1—C10—C11—C12	−177.0 (4)	C5—C1—Fe1—C3	80.4 (5)
C10—C11—C12—C13	−1.3 (9)	C2—C1—Fe1—C3	−36.3 (4)
C11—C12—C13—C14	0.1 (10)	C2—C1—Fe1—C5	−116.7 (6)
C12—C13—C14—C15	0.4 (11)	C2—C3—Fe1—C7	−46.6 (5)
C13—C14—C15—C10	0.3 (11)	C4—C3—Fe1—C7	−164.7 (4)
C11—C10—C15—C14	−1.4 (9)	C2—C3—Fe1—C6	−145.7 (4)
S1—C10—C15—C14	177.6 (5)	C4—C3—Fe1—C6	96.2 (4)
C9—C8—Fe1—C7	−160.1 (5)	C2—C3—Fe1—C8	119.7 (5)
C9—C8—Fe1—C6	−66.4 (5)	C4—C3—Fe1—C8	1.6 (7)
C9—C8—Fe1—C2	102.8 (6)	C4—C3—Fe1—C2	−118.1 (6)
C9—C8—Fe1—C4	32.3 (5)	C2—C3—Fe1—C4	118.1 (6)
C9—C8—Fe1—C1	100.9 (5)	C2—C3—Fe1—C1	37.6 (4)
C9—C8—Fe1—C3	31.2 (7)	C4—C3—Fe1—C1	−80.5 (4)
C9—C8—Fe1—C5	66.3 (4)	C2—C3—Fe1—C5	80.5 (4)
C3—C2—Fe1—C7	143.1 (4)	C4—C3—Fe1—C5	−37.6 (4)
C1—C2—Fe1—C7	−97.6 (5)	C4—C5—Fe1—C7	153.7 (5)
C3—C2—Fe1—C6	44.4 (5)	C1—C5—Fe1—C7	34.2 (6)
C1—C2—Fe1—C6	163.7 (4)	C4—C5—Fe1—C6	−37.4 (5)
C3—C2—Fe1—C8	−122.0 (6)	C1—C5—Fe1—C6	−156.9 (4)
C1—C2—Fe1—C8	−2.7 (8)	C4—C5—Fe1—C8	−121.1 (4)
C3—C2—Fe1—C4	−38.3 (4)	C1—C5—Fe1—C8	119.4 (4)
C1—C2—Fe1—C4	81.0 (5)	C4—C5—Fe1—C2	80.7 (5)
C3—C2—Fe1—C1	−119.3 (6)	C1—C5—Fe1—C2	−38.8 (4)
C1—C2—Fe1—C3	119.3 (6)	C1—C5—Fe1—C4	−119.5 (6)
C3—C2—Fe1—C5	−81.1 (4)	C4—C5—Fe1—C1	119.5 (6)
C1—C2—Fe1—C5	38.1 (4)	C4—C5—Fe1—C3	38.4 (4)
C5—C4—Fe1—C7	−76.5 (10)	C1—C5—Fe1—C3	−81.0 (5)
C3—C4—Fe1—C7	41.1 (10)	C15—C10—S1—C9	169.7 (5)
C5—C4—Fe1—C6	153.0 (4)	C11—C10—S1—C9	−11.5 (6)
C3—C4—Fe1—C6	−89.5 (4)	C8—C9—S1—C10	−175.3 (4)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₈H₉S)(CO)₂]
M_r	314.17
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	10.3992 (5), 7.6402 (4), 35.4173 (16)
V (Å³)	2814.0 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.57 × 0.27 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Integration (SADABS; Bruker, 2009)
T_min, T_max	0.545, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	20490, 2752, 2339
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.153, 1.26
No. of reflections	2752
No. of parameters	172
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.P)² + 19.462P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.75

Computer programs: APEX2 (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2009).

Acknowledgements

The authors thank Dr Manuel Fernandes for data collection, the NRF and the University of KwaZulu-Natal for financial support.

References

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