Dicarbon­yl(pyrazine-1,3-dithiol­ato-κ2S,S′)bis­(trimethyl­phosphane-κP)iron(II)

Gao, S.; Duan, Q.; An, C.; Jiang, D.

doi:10.1107/S1600536811048574

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1790

https://doi.org/10.1107/S1600536811048574

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Dicarbonyl(pyrazine-1,3-dithiolato-κ²S,S′)bis(trimethylphosphane-κP)iron(II)

Shang Gao,^a ^* Qian Duan,^a Chun-ai An ^a and Da-yong Jiang ^a

^aSchool of Materials Science and Engineering, Changchun University of Science and Technology, No. 7989 Weixing Road, Changchun 130022, People's Republic of China
^*Correspondence e-mail: cust_gaoshang@yahoo.cn

(Received 9 November 2011; accepted 15 November 2011; online 19 November 2011)

The title compound, [Fe(C₄H₂N₂S₂)(C₃H₉P)₂(CO)₂], was obtained as a mononuclear by-product during the treatment of [Fe₂(μ-S₂C₄N₂H₂)(CO)₆] in excess trimethylphosphane. The Fe atom is six-coordinated by two thiolate S atoms, two phosphane P atoms and two carbonyl C atoms in a distorted octahedral geometry. The average Fe—C(O) distance (1.771 Å) is relatively shorter than that of its parent hexacarbonyldiiron compound, and differs by 0.511 Å from the average Fe—P(Me)₃ distance. The five-membered FeC₂S₂ chelate ring plane is close to being perpendicular to the P/Fe/P plane [86.5 (2)°].

Related literature

For general background to iron sulfides, see: Cody et al. (2000 ); Georgakaki et al. (2003 ); Capon et al. (2005 ); Song (2005 ); Li et al. (2005 ); Liu & Xiao (2011 ). For related structures and the synthesis, see: Durgaprasad et al. (2011 ).

Experimental

Crystal data

[Fe(C₄H₂N₂S₂)(C₃H₉P)₂(CO)₂]
M_r = 406.21
Orthorhombic, P b c a
a = 12.2078 (10) Å
b = 11.951 (1) Å
c = 25.326 (2) Å
V = 3694.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 1.22 mm⁻¹
T = 273 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.711, T_max = 0.793
18679 measured reflections
3628 independent reflections
3166 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.073
S = 1.09
3628 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Selected bond lengths (Å)

Fe1—C8	1.761 (2)
Fe1—C7	1.780 (2)
Fe1—P1	2.2793 (6)
Fe1—P2	2.2840 (6)
Fe1—S2	2.3058 (6)
Fe1—S1	2.3170 (6)

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048574/kp2368sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048574/kp2368Isup2.hkl

checkCIF report

Comment top

Recently iron sulfides have been proposed as being central to the emergence of life due to their structural resemblance to the active site of hydrogenases (Cody et al., 2000, Georgakaki et al., 2003, Capon et al., 2005). Various dinuclear complexes featured [Fe₂(µ-SR)₂(CO)_6-_γL_γ] (L = CO, PR₃ et al., γ = 1 or 2) have been investigated as the structural and functional models for the active site of [FeFe]-hydrogenases (Song, 2005, Li et al., 2005, Liu & Xiao, 2011). [Fe₂(µ-S₂C₄N₂H₂)(CO)₆] (Durgaprasad et al., 2011) was prepared for the purpose to lower the reduction potentials of the iron sulfides. When we investigated the CO displacement of above complex by PMe₃, a mononuclear byproduct was obtained accompanied with PMe₃-disubstituted diiron compounds. Herein, we report this crystal structure.

In the title compound the central Fe atom is six-coordinated by the two thiolate-sulfur atoms, two phosphane-phosphorus atoms, and two carbonyl-carbon atoms in a distorted octahedral geometry (Fig. 1 and Table 1). The average Fe—C(O) distance (1.77 Å) is relatively shorter than that of its parent hexacarbonyl diiron compound [Fe₂(µ-S₂C₄N₂H₂)(CO)₆] (Durgaprasad et al., 2011), and differs by 0.51 Å from the average Fe—P(Me)₃ distance, consistent with the better donating role of the tertiary phosphane ligands vs. the carbonyl groups. The two S—Fe bonds are nearly perpendicular, and S1—Fe1—S2 angle is 89.198 (19) °. The P1—Fe1—P2 angle is quasilinear [177.45 (2) °] and the deviation of the iron atom from the calculated plane of the –SC₄N₂H₂S– bridge is 0.126 Å. The angle between the calculated rigid dithiolate bridge and the P1Fe1P2 plane deviates from 90° by 3.2° for the title compound, resulting in the asymmetric molecular structure.

Related literature top

For general background to iron sulfides, see: Cody et al. (2000); Georgakaki et al. (2003); Capon et al. (2005); Song (2005); Li et al. (2005); Liu & Xiao (2011). For related structures and the synthesis, see: Durgaprasad et al. (2011).

Experimental top

Commercially available materials, Me₃NO and trimethylphosphane were reagent grade and used as received. The starting material [Fe₂(µ-S₂C₄N₂H₂)(CO)₆] was prepared according to the literature procedure (Durgaprasad et al., 2011). [Fe₂(µ-S₂C₄N₂H₂)(CO)₆] (0.42 g, 1.0 mmol) and degassed CH₃CN (20 ml) was stirred in an argon-filled Schlenk flask until the salvation was completed. Me₃NO (0.24 g, 2.2 mmol) was added to the above solution in one portion. The mixture was changed to dark red after 10 min. Then the trimethylphosphane (0.15 g, 2.0 mmol) was added dropwise. The solvent was allowed to evaporate on a rotary evaporator after 20 min. The crude product was purified by column chromatography on Al₂O₃, using CH₂Cl₂/hexane as eluent, yielded two bands. The coral band was collected and the crystals of the title compound suitable for X-ray study were obtained by the recrystallization in the CH₂Cl₂/pentane solution (yield 0.12 g, 30%).

Structure description top

For general background to iron sulfides, see: Cody et al. (2000); Georgakaki et al. (2003); Capon et al. (2005); Song (2005); Li et al. (2005); Liu & Xiao (2011). For related structures and the synthesis, see: Durgaprasad et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2005); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.

Dicarbonyl(pyrazine-1,3-dithiolato- κ²S,S')bis(trimethylphosphane-κP)iron(II) top

Crystal data top

[Fe(C₄H₂N₂S₂)(C₃H₉P)₂(CO)₂]	F(000) = 1680
M_r = 406.21	D_x = 1.460 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9947 reflections
a = 12.2078 (10) Å	θ = 2.3–27.5°
b = 11.951 (1) Å	µ = 1.22 mm⁻¹
c = 25.326 (2) Å	T = 273 K
V = 3694.9 (5) Å³	Block, orange
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3628 independent reflections
Radiation source: fine-focus sealed tube	3166 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→14
T_min = 0.711, T_max = 0.793	k = −14→8
18679 measured reflections	l = −31→31

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0363P)² + 1.1092P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.073	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.30 e Å⁻³
3628 reflections	Δρ_min = −0.56 e Å⁻³
190 parameters

Crystal data top

[Fe(C₄H₂N₂S₂)(C₃H₉P)₂(CO)₂]	V = 3694.9 (5) Å³
M_r = 406.21	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.2078 (10) Å	µ = 1.22 mm⁻¹
b = 11.951 (1) Å	T = 273 K
c = 25.326 (2) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3628 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3166 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.793	R_int = 0.025
18679 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.09	Δρ_max = 0.30 e Å⁻³
3628 reflections	Δρ_min = −0.56 e Å⁻³
190 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

	x	y	z	U_iso*/U_eq
Fe1	0.374999 (19)	0.76447 (2)	0.389085 (10)	0.03519 (9)
S1	0.38945 (4)	0.57419 (4)	0.37296 (2)	0.04420 (13)
P2	0.39648 (4)	0.71975 (5)	0.47615 (2)	0.04635 (14)
S2	0.56151 (4)	0.78108 (4)	0.37704 (2)	0.05021 (14)
P1	0.35858 (4)	0.80265 (5)	0.30127 (2)	0.04756 (14)
O1	0.13778 (12)	0.74340 (14)	0.39685 (7)	0.0643 (4)
C7	0.23021 (16)	0.75098 (15)	0.39447 (7)	0.0430 (4)
C9	0.60519 (15)	0.64370 (18)	0.36700 (7)	0.0446 (4)
O2	0.38260 (15)	1.00089 (14)	0.41494 (8)	0.0817 (5)
C10	0.53051 (15)	0.55283 (16)	0.36640 (6)	0.0407 (4)
N1	0.56545 (15)	0.44788 (15)	0.36180 (6)	0.0519 (4)
C8	0.37676 (16)	0.90822 (17)	0.40424 (9)	0.0502 (5)
C12	0.74509 (18)	0.5207 (2)	0.35593 (9)	0.0667 (7)
H12A	0.8193	0.5059	0.3516	0.080*
C11	0.6742 (2)	0.4338 (2)	0.35706 (7)	0.0589 (6)
H11A	0.7018	0.3615	0.3545	0.071*
C6	0.52289 (18)	0.6505 (2)	0.49459 (9)	0.0626 (6)
H6A	0.5227	0.6361	0.5319	0.094*
H6B	0.5839	0.6978	0.4859	0.094*
H6C	0.5291	0.5811	0.4757	0.094*
N2	0.71250 (14)	0.62810 (18)	0.36084 (7)	0.0612 (5)
C2	0.2200 (2)	0.8015 (3)	0.27602 (9)	0.0830 (9)
H2B	0.2208	0.8183	0.2390	0.125*
H2C	0.1772	0.8567	0.2943	0.125*
H2D	0.1883	0.7289	0.2814	0.125*
C3	0.4080 (3)	0.9401 (3)	0.28305 (11)	0.0997 (11)
H3A	0.3988	0.9508	0.2457	0.150*
H3B	0.4842	0.9463	0.2919	0.150*
H3C	0.3671	0.9961	0.3018	0.150*
C4	0.29368 (19)	0.6241 (2)	0.50169 (9)	0.0728 (7)
H4A	0.3080	0.6093	0.5383	0.109*
H4B	0.2963	0.5552	0.4822	0.109*
H4C	0.2224	0.6571	0.4981	0.109*
C1	0.4288 (2)	0.7111 (3)	0.25558 (10)	0.0827 (8)
H1B	0.4155	0.7358	0.2201	0.124*
H1C	0.4021	0.6361	0.2598	0.124*
H1D	0.5060	0.7129	0.2626	0.124*
C5	0.3912 (3)	0.8351 (3)	0.52247 (11)	0.0983 (11)
H5A	0.4011	0.8073	0.5577	0.147*
H5B	0.3213	0.8716	0.5199	0.147*
H5C	0.4483	0.8876	0.5144	0.147*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03369 (15)	0.03112 (15)	0.04075 (16)	0.00071 (9)	−0.00012 (10)	0.00066 (10)
S1	0.0391 (2)	0.0349 (2)	0.0586 (3)	−0.00252 (18)	0.00205 (19)	−0.0062 (2)
P2	0.0529 (3)	0.0452 (3)	0.0409 (3)	0.0026 (2)	−0.0055 (2)	−0.0013 (2)
S2	0.0355 (2)	0.0422 (3)	0.0729 (3)	−0.0058 (2)	0.0009 (2)	0.0035 (2)
P1	0.0472 (3)	0.0532 (3)	0.0423 (3)	−0.0029 (2)	−0.0002 (2)	0.0065 (2)
O1	0.0383 (8)	0.0691 (11)	0.0856 (12)	0.0028 (7)	0.0084 (7)	0.0101 (9)
C7	0.0424 (11)	0.0387 (10)	0.0479 (10)	0.0035 (8)	0.0032 (8)	0.0037 (8)
C9	0.0377 (9)	0.0518 (11)	0.0442 (10)	0.0056 (8)	0.0000 (7)	0.0026 (9)
O2	0.0976 (14)	0.0380 (9)	0.1097 (15)	0.0031 (8)	−0.0022 (11)	−0.0105 (9)
C10	0.0428 (10)	0.0435 (10)	0.0358 (9)	0.0075 (8)	0.0015 (7)	−0.0015 (8)
N1	0.0616 (11)	0.0483 (10)	0.0458 (9)	0.0136 (8)	0.0018 (7)	−0.0040 (7)
C8	0.0510 (11)	0.0384 (11)	0.0613 (12)	0.0032 (8)	−0.0005 (9)	0.0009 (9)
C12	0.0460 (12)	0.0879 (19)	0.0661 (14)	0.0269 (13)	0.0043 (10)	0.0017 (13)
C11	0.0665 (14)	0.0675 (15)	0.0428 (10)	0.0308 (13)	0.0019 (9)	−0.0026 (10)
C6	0.0600 (13)	0.0693 (15)	0.0584 (12)	0.0014 (11)	−0.0192 (10)	0.0096 (11)
N2	0.0382 (9)	0.0730 (13)	0.0723 (12)	0.0083 (9)	0.0024 (8)	0.0048 (10)
C2	0.0597 (14)	0.135 (3)	0.0548 (13)	0.0022 (16)	−0.0134 (11)	0.0142 (15)
C3	0.152 (3)	0.081 (2)	0.0660 (16)	−0.043 (2)	−0.0189 (17)	0.0327 (15)
C4	0.0638 (14)	0.099 (2)	0.0552 (12)	−0.0068 (14)	0.0009 (11)	0.0253 (13)
C1	0.0862 (18)	0.112 (2)	0.0493 (13)	0.0191 (17)	0.0164 (12)	−0.0033 (14)
C5	0.160 (3)	0.076 (2)	0.0591 (15)	0.0244 (19)	−0.0146 (17)	−0.0217 (14)

Geometric parameters (Å, º) top

Fe1—C8	1.761 (2)	C12—C11	1.352 (4)
Fe1—C7	1.780 (2)	C12—H12A	0.9300
Fe1—P1	2.2793 (6)	C11—H11A	0.9300
Fe1—P2	2.2840 (6)	C6—H6A	0.9600
Fe1—S2	2.3058 (6)	C6—H6B	0.9600
Fe1—S1	2.3170 (6)	C6—H6C	0.9600
S1—C10	1.7488 (18)	C2—H2B	0.9600
P2—C5	1.811 (3)	C2—H2C	0.9600
P2—C6	1.812 (2)	C2—H2D	0.9600
P2—C4	1.817 (2)	C3—H3A	0.9600
S2—C9	1.745 (2)	C3—H3B	0.9600
P1—C1	1.808 (2)	C3—H3C	0.9600
P1—C2	1.809 (2)	C4—H4A	0.9600
P1—C3	1.810 (3)	C4—H4B	0.9600
O1—C7	1.134 (2)	C4—H4C	0.9600
C9—N2	1.332 (2)	C1—H1B	0.9600
C9—C10	1.418 (3)	C1—H1C	0.9600
O2—C8	1.142 (3)	C1—H1D	0.9600
C10—N1	1.330 (3)	C5—H5A	0.9600
N1—C11	1.343 (3)	C5—H5B	0.9600
C12—N2	1.349 (3)	C5—H5C	0.9600

C8—Fe1—C7	94.81 (9)	N1—C11—C12	122.6 (2)
C8—Fe1—P1	91.05 (7)	N1—C11—H11A	118.7
C7—Fe1—P1	90.32 (6)	C12—C11—H11A	118.7
C8—Fe1—P2	90.95 (7)	P2—C6—H6A	109.5
C7—Fe1—P2	91.08 (6)	P2—C6—H6B	109.5
P1—Fe1—P2	177.45 (2)	H6A—C6—H6B	109.5
C8—Fe1—S2	86.14 (6)	P2—C6—H6C	109.5
C7—Fe1—S2	176.78 (6)	H6A—C6—H6C	109.5
P1—Fe1—S2	86.58 (2)	H6B—C6—H6C	109.5
P2—Fe1—S2	91.98 (2)	C9—N2—C12	115.7 (2)
C8—Fe1—S1	174.39 (7)	P1—C2—H2B	109.5
C7—Fe1—S1	90.01 (6)	P1—C2—H2C	109.5
P1—Fe1—S1	91.79 (2)	H2B—C2—H2C	109.5
P2—Fe1—S1	86.09 (2)	P1—C2—H2D	109.5
S2—Fe1—S1	89.198 (19)	H2B—C2—H2D	109.5
C10—S1—Fe1	103.59 (7)	H2C—C2—H2D	109.5
C5—P2—C6	102.18 (13)	P1—C3—H3A	109.5
C5—P2—C4	102.93 (15)	P1—C3—H3B	109.5
C6—P2—C4	102.08 (12)	H3A—C3—H3B	109.5
C5—P2—Fe1	116.29 (10)	P1—C3—H3C	109.5
C6—P2—Fe1	116.96 (8)	H3A—C3—H3C	109.5
C4—P2—Fe1	114.31 (8)	H3B—C3—H3C	109.5
C9—S2—Fe1	103.89 (7)	P2—C4—H4A	109.5
C1—P1—C2	102.28 (13)	P2—C4—H4B	109.5
C1—P1—C3	103.18 (15)	H4A—C4—H4B	109.5
C2—P1—C3	103.19 (14)	P2—C4—H4C	109.5
C1—P1—Fe1	117.49 (9)	H4A—C4—H4C	109.5
C2—P1—Fe1	115.19 (8)	H4B—C4—H4C	109.5
C3—P1—Fe1	113.66 (9)	P1—C1—H1B	109.5
O1—C7—Fe1	178.51 (19)	P1—C1—H1C	109.5
N2—C9—C10	121.58 (19)	H1B—C1—H1C	109.5
N2—C9—S2	116.69 (17)	P1—C1—H1D	109.5
C10—C9—S2	121.72 (14)	H1B—C1—H1D	109.5
N1—C10—C9	121.13 (17)	H1C—C1—H1D	109.5
N1—C10—S1	117.51 (15)	P2—C5—H5A	109.5
C9—C10—S1	121.35 (14)	P2—C5—H5B	109.5
C10—N1—C11	116.28 (19)	H5A—C5—H5B	109.5
O2—C8—Fe1	176.9 (2)	P2—C5—H5C	109.5
N2—C12—C11	122.7 (2)	H5A—C5—H5C	109.5
N2—C12—H12A	118.7	H5B—C5—H5C	109.5
C11—C12—H12A	118.7

C8—Fe1—S1—C10	−29.4 (8)	S2—Fe1—P1—C2	178.35 (12)
C7—Fe1—S1—C10	−178.74 (8)	S1—Fe1—P1—C2	89.26 (12)
P1—Fe1—S1—C10	90.93 (6)	C8—Fe1—P1—C3	23.20 (15)
P2—Fe1—S1—C10	−87.66 (6)	C7—Fe1—P1—C3	118.01 (15)
S2—Fe1—S1—C10	4.37 (6)	P2—Fe1—P1—C3	−118.6 (5)
C8—Fe1—P2—C5	6.40 (15)	S2—Fe1—P1—C3	−62.87 (13)
C7—Fe1—P2—C5	−88.43 (14)	S1—Fe1—P1—C3	−151.96 (13)
P1—Fe1—P2—C5	148.2 (5)	C8—Fe1—C7—O1	78 (8)
S2—Fe1—P2—C5	92.57 (13)	P1—Fe1—C7—O1	−13 (8)
S1—Fe1—P2—C5	−178.37 (13)	P2—Fe1—C7—O1	169 (8)
C8—Fe1—P2—C6	−114.62 (11)	S2—Fe1—C7—O1	−29 (9)
C7—Fe1—P2—C6	150.55 (11)	S1—Fe1—C7—O1	−105 (8)
P1—Fe1—P2—C6	27.1 (5)	Fe1—S2—C9—N2	−177.54 (14)
S2—Fe1—P2—C6	−28.45 (9)	Fe1—S2—C9—C10	1.34 (16)
S1—Fe1—P2—C6	60.61 (9)	N2—C9—C10—N1	2.8 (3)
C8—Fe1—P2—C4	126.20 (12)	S2—C9—C10—N1	−176.04 (14)
C7—Fe1—P2—C4	31.37 (12)	N2—C9—C10—S1	−178.48 (14)
P1—Fe1—P2—C4	−92.0 (5)	S2—C9—C10—S1	2.7 (2)
S2—Fe1—P2—C4	−147.63 (10)	Fe1—S1—C10—N1	173.69 (13)
S1—Fe1—P2—C4	−58.57 (10)	Fe1—S1—C10—C9	−5.10 (16)
C8—Fe1—S2—C9	173.53 (10)	C9—C10—N1—C11	−0.9 (3)
C7—Fe1—S2—C9	−79.2 (11)	S1—C10—N1—C11	−179.71 (13)
P1—Fe1—S2—C9	−95.18 (7)	C7—Fe1—C8—O2	153 (4)
P2—Fe1—S2—C9	82.72 (7)	P1—Fe1—C8—O2	−117 (4)
S1—Fe1—S2—C9	−3.34 (7)	P2—Fe1—C8—O2	62 (4)
C8—Fe1—P1—C1	143.77 (13)	S2—Fe1—C8—O2	−30 (4)
C7—Fe1—P1—C1	−121.41 (13)	S1—Fe1—C8—O2	4 (5)
P2—Fe1—P1—C1	2.0 (5)	C10—N1—C11—C12	−1.2 (3)
S2—Fe1—P1—C1	57.70 (12)	N2—C12—C11—N1	1.8 (3)
S1—Fe1—P1—C1	−31.39 (12)	C10—C9—N2—C12	−2.2 (3)
C8—Fe1—P1—C2	−95.58 (14)	S2—C9—N2—C12	176.63 (16)
C7—Fe1—P1—C2	−0.76 (13)	C11—C12—N2—C9	0.1 (3)
P2—Fe1—P1—C2	122.7 (5)

Experimental details

Crystal data
Chemical formula	[Fe(C₄H₂N₂S₂)(C₃H₉P)₂(CO)₂]
M_r	406.21
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	273
a, b, c (Å)	12.2078 (10), 11.951 (1), 25.326 (2)
V (Å³)	3694.9 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.22
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.711, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections	18679, 3628, 3166
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.073, 1.09
No. of reflections	3628
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.56

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Fe1—C8	1.761 (2)	Fe1—P2	2.2840 (6)
Fe1—C7	1.780 (2)	Fe1—S2	2.3058 (6)
Fe1—P1	2.2793 (6)	Fe1—S1	2.3170 (6)

Acknowledgements

The authors thank the Scientific and Technological Development Project of Jilin Province (No. 201101103) and the National Natural Science Foundation of China (No. 61106050) for financial support.

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