Bis[1,2-bis­(eth­oxy­carbon­yl)ethene-1,2-dithiol­ato-κ2S,S′]bis­(η5-penta­methyl­cyclo­penta­dien­yl)tetra-μ3-sulfido-diiron(IV)diiron(III)(3 Fe—Fe)

Ito, S.; Hisamichi, N.; Takase, T.; Inomata, S.

doi:10.1107/S1600536813005564

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page m181

doi:10.1107/S1600536813005564

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Bis[1,2-bis(ethoxycarbonyl)ethene-1,2-dithiolato-κ²S,S′]bis(η⁵-pentamethylcyclopentadienyl)tetra-μ₃-sulfido-diiron(IV)diiron(III)(3 Fe—Fe)

Shohei Ito,^a Nozomu Hisamichi,^a Tsugiko Takase ^b and Shinji Inomata ^a ^*

^aFaculty of Symbiotic Systems Science, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan, and ^bCenter for Practical and Project-Based Learning, Cluster of Science and Technology, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan
^*Correspondence e-mail: inomata@sss.fukushima-u.ac.jp

(Received 12 February 2013; accepted 26 February 2013; online 2 March 2013)

The title compound, [Fe₄(C₁₀H₁₅)₂(C₈H₁₀O₄S₂)₂S₄], contains a twisted Fe₄S₄ cubane-like core. A twofold rotation axis passes through the Fe₄S₄ core, completing the coordination of the four Fe atoms with two pentamethylcyclopentadienyl ligands and two chelating dithiolate ligands. There are three short Fe—Fe and three long Fe⋯Fe contacts in the Fe₄S₄ core, suggesting bonding and non-bonding interactions, respectively. The Fe—S bonds in the Fe₄S₄ core range from 2.1523 (5) to 2.2667 (6) Å and are somewhat longer than the Fe—S bonds involving the dithiolate ligand.

Related literature

For details of the synthesis, see: Inomata et al. (1995 ). For related structures, see: Inomata et al. (1990 , 1994 ). For general background to compounds with iron–sulfur cubane-type clusters, see: Holm (1977 ); Holm et al. (1990 ).

Experimental

Crystal data

[Fe₄(C₁₀H₁₅)₂(C₈H₁₀O₄S₂)₂S₄]
M_r = 1090.65
Monoclinic, C 2/c
a = 23.4532 (5) Å
b = 10.4466 (2) Å
c = 18.3113 (3) Å
β = 90.6186 (7)°
V = 4486.14 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.69 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.560, T_max = 0.714
21429 measured reflections
5111 independent reflections
4694 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.080
S = 1.06
5111 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected bond lengths (Å)

Fe1—Fe1ⁱ	3.3743 (3)
Fe1—Fe2	2.7253 (4)
Fe1—Fe2ⁱ	3.2683 (3)
Fe1—S1	2.1956 (5)
Fe1—S1ⁱ	2.2551 (5)
Fe1—S2	2.1749 (5)
Fe2—Fe2ⁱ	2.7619 (3)
Fe2—S1	2.2736 (5)
Fe2—S2	2.1523 (5)
Fe2—S2ⁱ	2.2667 (6)
Fe2—S3	2.1541 (5)
Fe2—S4	2.1934 (6)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2006 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: CrystalStructure (Rigaku, 2006).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813005564/wm2725sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005564/wm2725Isup2.hkl

checkCIF report

Comment top

Iron-sulfur cubane-type clusters have extensively been investigated as model systems of metal-containing proteins (Holm, 1977; Holm et al., 1990). Among these compounds, the Fe₄S₄ core is usually surrounded by the same supporting ligand (L) yielding a moiety Fe₄S₄L₄. However, mixed-ligand-type clusters are rather rare. Previously, we succeeded to prepare this type of iron-sulfur cluster from the reaction of (C₅Me₅)₂Fe₂(CO)₄ ((Cp*)₂Fe₂(CO)₄) with S₈ and diphenylacetylene (Inomata et al., 1990; 1994). One of the products was [Fe₄(Cp*)₂(Ph₂C₂S₂)₂(µ₃-S)₄], in which two Cp* ligands and two diphenyldithiolate ligands are additionally bonded to the Fe₄S₄ core. In order to expand our research on this subject, we prepared a cluster containg bis(ethoxycarbonyl)dithiolate ligands instead of diphenyldithiolate ligands. Here we report the structural details of the title compound [Fe₄(C₁₀H₁₅)₂(C₈H₁₀O₄S₂)₂S₄] or [Fe₄(Cp*)₂{(EtO₂C)₂C₂S₂)}₂(µ₃-S)₄], (I).

Compound (I) contains a twisted Fe₄S₄ cubane-like core surrounded by two Cp* ligands and two dithiolato ligands {(EtO₂C)₂C₂S₂} (Fig. 1). A crystallographic twofold rotation axis passes through the Fe₄S₄ core and completes the coordination environment of all iron atoms. There are three iron—iron bonds of 2.7253 (4) and 2.7619 (3) Å (Table 1). The remaining three Fe···Fe distances are very long (3.2683 (3) and 3.3743 (3) Å), indicating no bonding interactions (Table 1). The iron—sulfur distances in the Fe₄S₄ core range from 2.1523 (5) to 2.2667 (6) Å and are normal values (Table 1). On the other hand, the distances between iron and sulfur in the dithiolato ligand are somewhat short (2.1541 (5) and 2.1934 (6) Å) (Table 1).

Related literature top

For details of the synthesis, see: Inomata et al. (1995). For related structures, see: Inomata et al. (1990, 1994). For general background to compounds with iron–sulfur cubane-type clusters, see: Holm (1977); Holm et al. (1990).

Experimental top

The title cluster compound was prepared according to the literature method (Inomata et al., 1995) by using diethyl acetylenedicarboxylate instead of dimethyl acetylenedicarboxylate.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2006).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and displacement ellipsoids at the 30% probability level. All hydrogen atoms were omitted for clarity. Solid lines indicate short Fe—Fe contacts.

Bis[1,2-bis(ethoxycarbonyl)ethene-1,2-dithiolato-κ²S,S']bis(η⁵-pentamethylcyclopentadienyl)tetra-µ₃-sulfido-diiron(IV)diiron(III)(3 Fe—Fe) top

Crystal data top

[Fe₄(C₁₀H₁₅)₂(C₈H₁₀O₄S₂)₂S₄]	F(000) = 2248.00
M_r = 1090.65	D_x = 1.615 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 18942 reflections
a = 23.4532 (5) Å	θ = 3.1–27.5°
b = 10.4466 (2) Å	µ = 1.69 mm⁻¹
c = 18.3113 (3) Å	T = 296 K
β = 90.6186 (7)°	Block, black
V = 4486.14 (15) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4694 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.044
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −30→30
T_min = 0.560, T_max = 0.714	k = −13→13
21429 measured reflections	l = −23→23
5111 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.037P)² + 5.9377P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.080	(Δ/σ)_max = 0.002
S = 1.06	Δρ_max = 0.50 e Å⁻³
5111 reflections	Δρ_min = −0.33 e Å⁻³
254 parameters

Crystal data top

[Fe₄(C₁₀H₁₅)₂(C₈H₁₀O₄S₂)₂S₄]	V = 4486.14 (15) Å³
M_r = 1090.65	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.4532 (5) Å	µ = 1.69 mm⁻¹
b = 10.4466 (2) Å	T = 296 K
c = 18.3113 (3) Å	0.30 × 0.20 × 0.20 mm
β = 90.6186 (7)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5111 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	4694 reflections with I > 2σ(I)
T_min = 0.560, T_max = 0.714	R_int = 0.044
21429 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	254 parameters
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	Δρ_max = 0.50 e Å⁻³
5111 reflections	Δρ_min = −0.33 e Å⁻³

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.512641 (12)	0.27575 (3)	0.159470 (14)	0.02745 (7)
Fe2	0.449295 (12)	0.07723 (3)	0.210955 (14)	0.02769 (7)
S1	0.43972 (2)	0.29022 (4)	0.23321 (3)	0.02894 (11)
S2	0.53399 (2)	0.07354 (4)	0.16691 (3)	0.03038 (11)
S3	0.38310 (2)	0.09718 (5)	0.12928 (3)	0.03767 (13)
S4	0.42061 (2)	−0.11994 (5)	0.22914 (3)	0.03867 (13)
O1	0.25875 (9)	−0.1373 (2)	0.08613 (13)	0.0745 (6)
O2	0.29459 (8)	0.02895 (19)	0.02550 (11)	0.0590 (4)
O3	0.33671 (9)	−0.35409 (19)	0.13925 (13)	0.0668 (5)
O4	0.29995 (10)	−0.2666 (2)	0.23969 (11)	0.0675 (5)
C1	0.56426 (10)	0.4192 (2)	0.10976 (12)	0.0416 (5)
C2	0.50644 (10)	0.4620 (2)	0.11373 (11)	0.0382 (4)
C3	0.47177 (10)	0.3774 (2)	0.07124 (11)	0.0388 (4)
C4	0.50767 (12)	0.2819 (2)	0.04178 (11)	0.0414 (5)
C5	0.56502 (11)	0.3076 (2)	0.06575 (12)	0.0442 (5)
C6	0.61503 (13)	0.4854 (3)	0.14245 (16)	0.0642 (7)
C7	0.48533 (15)	0.5815 (2)	0.14991 (15)	0.0594 (7)
C8	0.40936 (12)	0.3974 (2)	0.05670 (16)	0.0555 (6)
C9	0.48970 (16)	0.1760 (2)	−0.00894 (14)	0.0658 (8)
C10	0.61697 (14)	0.2362 (3)	0.04239 (17)	0.0709 (9)
C11	0.34615 (9)	−0.0459 (2)	0.12687 (12)	0.0364 (4)
C12	0.36250 (9)	−0.1409 (2)	0.17332 (12)	0.0351 (4)
C13	0.29508 (10)	−0.0580 (2)	0.07860 (13)	0.0425 (5)
C14	0.33153 (10)	−0.2667 (2)	0.18025 (14)	0.0430 (5)
C15	0.24678 (14)	0.0240 (3)	−0.02537 (17)	0.0716 (8)
C16	0.2579 (2)	0.1231 (4)	−0.0829 (2)	0.0961 (13)
C17	0.26445 (15)	−0.3807 (3)	0.25262 (19)	0.0764 (9)
C18	0.20954 (15)	−0.3640 (3)	0.2128 (2)	0.0809 (9)
H1	0.6029	0.5612	0.1675	0.077*
H2	0.6410	0.5084	0.1044	0.077*
H3	0.6338	0.4290	0.1764	0.077*
H4	0.5163	0.6223	0.1754	0.071*
H5	0.4702	0.6387	0.1136	0.071*
H6	0.4560	0.5599	0.1839	0.071*
H7	0.3950	0.3287	0.0269	0.067*
H8	0.4038	0.4772	0.0317	0.067*
H9	0.3894	0.3990	0.1022	0.067*
H10	0.5225	0.1265	−0.0222	0.079*
H11	0.4725	0.2119	−0.0521	0.079*
H12	0.4627	0.1218	0.0151	0.079*
H13	0.6502	0.2752	0.0638	0.085*
H14	0.6197	0.2389	−0.0099	0.085*
H15	0.6144	0.1488	0.0582	0.085*
H16	0.2115	0.0425	−0.0004	0.086*
H17	0.2439	−0.0604	−0.0473	0.086*
H18	0.2415	0.2033	−0.0683	0.115*
H19	0.2409	0.0963	−0.1284	0.115*
H20	0.2982	0.1331	−0.0889	0.115*
H21	0.2576	−0.3905	0.3045	0.092*
H22	0.2838	−0.4567	0.2353	0.092*
H23	0.1826	−0.3224	0.2440	0.097*
H24	0.1950	−0.4463	0.1985	0.097*
H25	0.2155	−0.3126	0.1701	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03035 (15)	0.02725 (14)	0.02472 (14)	0.00053 (10)	−0.00037 (11)	0.00188 (10)
Fe2	0.02636 (14)	0.02784 (15)	0.02878 (14)	−0.00189 (10)	−0.00376 (10)	−0.00136 (10)
S1	0.0284 (2)	0.0298 (2)	0.0286 (2)	0.00303 (17)	−0.00230 (18)	−0.00054 (17)
S2	0.0330 (2)	0.0297 (2)	0.0284 (2)	0.00387 (18)	0.00056 (18)	−0.00021 (17)
S3	0.0369 (2)	0.0381 (2)	0.0377 (2)	−0.0058 (2)	−0.0122 (2)	0.0029 (2)
S4	0.0398 (2)	0.0289 (2)	0.0470 (2)	−0.0048 (2)	−0.0122 (2)	0.0007 (2)
O1	0.0465 (10)	0.0993 (16)	0.0771 (13)	−0.0314 (11)	−0.0221 (9)	0.0159 (12)
O2	0.0545 (10)	0.0647 (11)	0.0571 (10)	−0.0097 (9)	−0.0274 (8)	0.0042 (9)
O3	0.0607 (12)	0.0478 (10)	0.0923 (15)	−0.0169 (9)	0.0138 (10)	−0.0262 (10)
O4	0.0772 (14)	0.0671 (12)	0.0584 (11)	−0.0350 (11)	0.0157 (10)	−0.0072 (9)
C1	0.0466 (12)	0.0448 (12)	0.0332 (10)	−0.0098 (9)	0.0023 (9)	0.0112 (8)
C2	0.0525 (12)	0.0319 (9)	0.0299 (9)	−0.0015 (9)	−0.0011 (8)	0.0076 (7)
C3	0.0481 (12)	0.0378 (10)	0.0305 (9)	−0.0012 (9)	−0.0051 (8)	0.0094 (8)
C4	0.0636 (14)	0.0360 (10)	0.0247 (9)	−0.0021 (9)	0.0008 (9)	0.0052 (7)
C5	0.0504 (13)	0.0483 (12)	0.0341 (10)	0.0047 (10)	0.0125 (9)	0.0121 (9)
C6	0.0592 (16)	0.0761 (19)	0.0573 (15)	−0.0296 (15)	−0.0040 (13)	0.0159 (14)
C7	0.092 (2)	0.0336 (12)	0.0527 (14)	0.0044 (12)	0.0071 (14)	0.0020 (10)
C8	0.0519 (14)	0.0576 (15)	0.0567 (14)	0.0024 (12)	−0.0162 (12)	0.0211 (12)
C9	0.116 (2)	0.0464 (14)	0.0354 (12)	−0.0124 (15)	0.0032 (14)	−0.0037 (10)
C10	0.072 (2)	0.080 (2)	0.0621 (17)	0.0207 (16)	0.0324 (15)	0.0133 (15)
C11	0.0296 (9)	0.0423 (11)	0.0371 (10)	−0.0047 (8)	−0.0029 (8)	−0.0075 (8)
C12	0.0305 (9)	0.0353 (10)	0.0394 (10)	−0.0050 (8)	−0.0013 (8)	−0.0080 (8)
C13	0.0338 (11)	0.0514 (12)	0.0420 (11)	−0.0028 (9)	−0.0055 (9)	−0.0085 (9)
C14	0.0380 (11)	0.0391 (11)	0.0518 (12)	−0.0085 (9)	−0.0034 (9)	−0.0045 (9)
C15	0.0638 (18)	0.093 (2)	0.0575 (16)	0.0007 (16)	−0.0333 (14)	−0.0024 (16)
C16	0.123 (3)	0.090 (2)	0.074 (2)	0.005 (2)	−0.046 (2)	0.006 (2)
C17	0.076 (2)	0.081 (2)	0.0722 (19)	−0.0367 (18)	0.0011 (17)	0.0134 (17)
C18	0.0600 (19)	0.093 (2)	0.090 (2)	−0.0129 (18)	0.0156 (17)	0.012 (2)

Geometric parameters (Å, º) top

Fe1—Fe1ⁱ	3.3743 (3)	C4—C9	1.502 (3)
Fe1—Fe2	2.7253 (4)	C5—C10	1.495 (4)
Fe1—Fe2ⁱ	3.2683 (3)	C11—C12	1.360 (3)
Fe1—S1	2.1956 (5)	C11—C13	1.486 (3)
Fe1—S1ⁱ	2.2551 (5)	C12—C14	1.508 (3)
Fe1—S2	2.1749 (5)	C15—C16	1.503 (5)
Fe1—C1	2.136 (2)	C17—C18	1.483 (5)
Fe1—C2	2.122 (2)	C6—H1	0.960
Fe1—C3	2.150 (2)	C6—H2	0.960
Fe1—C4	2.158 (2)	C6—H3	0.960
Fe1—C5	2.147 (2)	C7—H4	0.960
Fe2—Fe2ⁱ	2.7619 (3)	C7—H6	0.960
Fe2—S1	2.2736 (5)	C7—H5	0.960
Fe2—S2	2.1523 (5)	C8—H7	0.960
Fe2—S2ⁱ	2.2667 (6)	C8—H8	0.960
Fe2—S3	2.1541 (5)	C8—H9	0.960
Fe2—S4	2.1934 (6)	C9—H10	0.960
S3—C11	1.728 (2)	C9—H11	0.960
S4—C12	1.709 (2)	C9—H12	0.960
O1—C13	1.198 (3)	C10—H13	0.960
O2—C13	1.330 (3)	C10—H14	0.960
O2—C15	1.451 (3)	C10—H15	0.960
O3—C14	1.189 (3)	C15—H16	0.970
O4—C14	1.323 (3)	C15—H17	0.970
O4—C17	1.474 (4)	C16—H18	0.960
C1—C2	1.431 (3)	C16—H19	0.960
C1—C5	1.417 (3)	C16—H20	0.960
C1—C6	1.496 (3)	C17—H21	0.970
C2—C3	1.426 (3)	C17—H22	0.970
C2—C7	1.500 (3)	C18—H23	0.960
C3—C4	1.416 (3)	C18—H24	0.960
C3—C8	1.500 (3)	C18—H25	0.960
C4—C5	1.435 (3)

Fe1···Fe1ⁱ	3.3743 (3)	Fe1···Fe2	2.7253 (4)
Fe2···Fe2ⁱ	2.7619 (3)	Fe1···Fe2ⁱ	3.2683 (3)
Fe1ⁱ···Fe2ⁱ	2.7253 (4)	Fe1ⁱ···Fe2	3.2683 (3)

Fe2—Fe1—S1	53.736 (13)	C2—C3—C4	107.8 (2)
Fe2—Fe1—S1ⁱ	90.938 (15)	C2—C3—C8	124.1 (2)
Fe2—Fe1—S2	50.595 (15)	C4—C3—C8	127.9 (2)
Fe2—Fe1—C1	174.13 (6)	Fe1—C4—C3	70.52 (11)
Fe2—Fe1—C2	143.01 (6)	Fe1—C4—C5	70.12 (12)
Fe2—Fe1—C3	113.29 (6)	Fe1—C4—C9	127.37 (16)
Fe2—Fe1—C4	110.15 (6)	C3—C4—C5	108.14 (19)
Fe2—Fe1—C5	135.48 (6)	C3—C4—C9	126.2 (2)
S1—Fe1—S1ⁱ	80.87 (2)	C5—C4—C9	125.6 (2)
S1—Fe1—S2	102.04 (2)	Fe1—C5—C1	70.25 (13)
S1—Fe1—C1	131.50 (6)	Fe1—C5—C4	70.93 (13)
S1—Fe1—C2	97.42 (6)	Fe1—C5—C10	128.82 (18)
S1—Fe1—C3	94.83 (6)	C1—C5—C4	108.0 (2)
S1—Fe1—C4	125.31 (7)	C1—C5—C10	126.0 (2)
S1—Fe1—C5	159.56 (6)	C4—C5—C10	125.7 (2)
S1ⁱ—Fe1—S2	84.20 (2)	S3—C11—C12	118.52 (16)
S1ⁱ—Fe1—C1	92.67 (6)	S3—C11—C13	119.31 (16)
S1ⁱ—Fe1—C2	108.28 (5)	C12—C11—C13	122.0 (2)
S1ⁱ—Fe1—C3	146.55 (6)	S4—C12—C11	119.90 (16)
S1ⁱ—Fe1—C4	152.77 (7)	S4—C12—C14	116.30 (16)
S1ⁱ—Fe1—C5	113.81 (6)	C11—C12—C14	123.80 (19)
S2—Fe1—C1	125.22 (6)	O1—C13—O2	123.8 (2)
S2—Fe1—C2	158.40 (6)	O1—C13—C11	124.1 (2)
S2—Fe1—C3	128.84 (6)	O2—C13—C11	112.2 (2)
S2—Fe1—C4	95.83 (6)	O3—C14—O4	125.6 (2)
S2—Fe1—C5	93.85 (6)	O3—C14—C12	124.3 (2)
C1—Fe1—C2	39.26 (8)	O4—C14—C12	110.0 (2)
C1—Fe1—C3	65.39 (8)	O2—C15—C16	106.7 (2)
C1—Fe1—C4	65.05 (8)	O4—C17—C18	108.4 (2)
C1—Fe1—C5	38.65 (8)	C1—C6—H1	109.5
C2—Fe1—C3	38.99 (8)	C1—C6—H2	109.5
C2—Fe1—C4	64.89 (8)	C1—C6—H3	109.5
C2—Fe1—C5	65.17 (8)	H1—C6—H2	109.5
C3—Fe1—C4	38.37 (8)	H1—C6—H3	109.5
C3—Fe1—C5	64.99 (8)	H2—C6—H3	109.5
C4—Fe1—C5	38.95 (9)	C2—C7—H4	109.5
Fe1—Fe2—Fe2ⁱ	73.111 (11)	C2—C7—H6	109.5
Fe1—Fe2—S1	51.138 (15)	C2—C7—H5	109.5
Fe1—Fe2—S2	51.334 (14)	H4—C7—H6	109.5
Fe1—Fe2—S2ⁱ	105.375 (16)	H4—C7—H5	109.5
Fe1—Fe2—S3	94.456 (17)	H6—C7—H5	109.5
Fe1—Fe2—S4	159.452 (19)	C3—C8—H7	109.5
Fe2ⁱ—Fe2—S1	89.620 (16)	C3—C8—H8	109.5
Fe2ⁱ—Fe2—S2	53.196 (16)	C3—C8—H9	109.5
Fe2ⁱ—Fe2—S2ⁱ	49.487 (14)	H7—C8—H8	109.5
Fe2ⁱ—Fe2—S3	165.837 (19)	H7—C8—H9	109.5
Fe2ⁱ—Fe2—S4	100.674 (17)	H8—C8—H9	109.5
S1—Fe2—S2	100.26 (2)	C4—C9—H10	109.5
S1—Fe2—S2ⁱ	81.730 (19)	C4—C9—H11	109.5
S1—Fe2—S3	87.59 (2)	C4—C9—H12	109.5
S1—Fe2—S4	149.40 (2)	H10—C9—H11	109.5
S2—Fe2—S2ⁱ	102.65 (2)	H10—C9—H12	109.5
S2—Fe2—S3	113.75 (2)	H11—C9—H12	109.5
S2—Fe2—S4	109.02 (2)	C5—C10—H13	109.5
S2ⁱ—Fe2—S3	143.35 (2)	C5—C10—H14	109.5
S2ⁱ—Fe2—S4	83.36 (2)	C5—C10—H15	109.5
S3—Fe2—S4	88.64 (2)	H13—C10—H14	109.5
Fe1—S1—Fe1ⁱ	98.59 (2)	H13—C10—H15	109.5
Fe1—S1—Fe2	75.126 (18)	H14—C10—H15	109.5
Fe1ⁱ—S1—Fe2	92.386 (19)	O2—C15—H16	110.4
Fe1—S2—Fe2	78.071 (18)	O2—C15—H17	110.4
Fe1—S2—Fe2ⁱ	94.73 (2)	C16—C15—H16	110.4
Fe2—S2—Fe2ⁱ	77.32 (2)	C16—C15—H17	110.4
Fe2—S3—C11	106.95 (7)	H16—C15—H17	108.6
Fe2—S4—C12	105.87 (7)	C15—C16—H18	109.5
C13—O2—C15	116.4 (2)	C15—C16—H19	109.5
C14—O4—C17	117.0 (2)	C15—C16—H20	109.5
Fe1—C1—C2	69.86 (12)	H18—C16—H19	109.5
Fe1—C1—C5	71.10 (13)	H18—C16—H20	109.5
Fe1—C1—C6	127.30 (17)	H19—C16—H20	109.5
C2—C1—C5	107.7 (2)	O4—C17—H21	110.0
C2—C1—C6	125.9 (2)	O4—C17—H22	110.0
C5—C1—C6	126.4 (2)	C18—C17—H21	110.0
Fe1—C2—C1	70.88 (12)	C18—C17—H22	110.0
Fe1—C2—C3	71.55 (12)	H21—C17—H22	108.4
Fe1—C2—C7	127.60 (15)	C17—C18—H23	109.5
C1—C2—C3	108.28 (18)	C17—C18—H24	109.5
C1—C2—C7	126.9 (2)	C17—C18—H25	109.5
C3—C2—C7	124.6 (2)	H23—C18—H24	109.5
Fe1—C3—C2	69.46 (11)	H23—C18—H25	109.5
Fe1—C3—C4	71.12 (12)	H24—C18—H25	109.5
Fe1—C3—C8	128.94 (16)

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe₄(C₁₀H₁₅)₂(C₈H₁₀O₄S₂)₂S₄]
M_r	1090.65
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	23.4532 (5), 10.4466 (2), 18.3113 (3)
β (°)	90.6186 (7)
V (Å³)	4486.14 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.69
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.560, 0.714
No. of measured, independent and observed [I > 2σ(I)] reflections	21429, 5111, 4694
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.06
No. of reflections	5111
No. of parameters	254
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.33

Computer programs: RAPID-AUTO (Rigaku, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), CrystalStructure (Rigaku, 2006).

Selected bond lengths (Å) top

Fe1—Fe1ⁱ	3.3743 (3)	Fe2—Fe2ⁱ	2.7619 (3)
Fe1—Fe2	2.7253 (4)	Fe2—S1	2.2736 (5)
Fe1—Fe2ⁱ	3.2683 (3)	Fe2—S2	2.1523 (5)
Fe1—S1	2.1956 (5)	Fe2—S2ⁱ	2.2667 (6)
Fe1—S1ⁱ	2.2551 (5)	Fe2—S3	2.1541 (5)
Fe1—S2	2.1749 (5)	Fe2—S4	2.1934 (6)

Symmetry code: (i) −x+1, y, −z+1/2.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Holm, R. H. (1977). Acc. Chem. Res. 12, 427–434. CrossRef Web of Science Google Scholar
Holm, R. H., Ciurli, S. & Weigel, J. A. (1990). Prog. Inorg. Chem. 38, 1–74. CrossRef CAS Web of Science Google Scholar
Inomata, S., Hiyama, K., Tobita, H. & Ogino, H. (1994). Inorg. Chem. 33, 5337–5342. CSD CrossRef CAS Web of Science Google Scholar
Inomata, S., Takano, H., Hiyama, K., Tobita, H. & Ogino, H. (1995). Organometallics, 14, 2112–2114. CSD CrossRef CAS Web of Science Google Scholar
Inomata, S., Tobita, H. & Ogino, H. (1990). J. Am. Chem. Soc. 112, 6145–6146. CSD CrossRef CAS Web of Science Google Scholar
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2006). CrystalStructure and RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 4| April 2013| Page m181

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