Penta­carbonyl-1κ2C,2κ3C-(μ-pyrazine-2,3-dithiol­ato-1:2κ4S,S′:S,S′)(trimethyl­phosphane-1κP)diiron(I)(Fe—Fe)

Gao, S.; An, C.-A.; Duan, Q.; Jiang, D.-Y.

doi:10.1107/S1600536811046770

Pentacarbonyl-1κ²C,2κ³C-(μ-pyrazine-2,3-dithiolato-1:2κ⁴S,S′:S,S′)(trimethylphosphane-1κP)diiron(I)(Fe—Fe)

S. Gao, C.-A. An, Q. Duan and D.-Y. Jiang

In the title compound, [Fe₂(C₄H₂N₂S₂)(C₃H₉P)(CO)₅], the Fe₂S₂ core adopts a butterfly conformation. The PMe₃ ligand is coordinated in the basal position, roughly cis to the Fe—Fe bond. The Fe—Fe distance of 2.4970 (6) Å is relatively short compared to those (ca 2.53 Å) found in another monosubstituted diiron compound. A rigid planar dithiolate bridge is featured, with an angle of 2.78 (1)° between the Fe—Fe bond and the normal to the pyrazine-2,3-dithiolate plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811046770/hy2484sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811046770/hy2484Isup2.hkl Contains datablock I

CCDC reference: 858169

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.005 Å
R factor = 0.034
wR factor = 0.070
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        273 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        273 K
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Fe1    --  C1      ..        5.5 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Fe1    --  C2      ..        8.0 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Fe1    --  C3      ..        5.5 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Fe2    --  S1      ..        5.8 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Fe2    --  C4      ..        5.5 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Fe2    --  C5      ..        6.0 su
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          !

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   2 ALERT type 5 Informative message, check

Comment top

Hydrogen evolution and uptake in nature is mostly catalyzed by the metalloenzymes called hydrogenases (Evans & Pickett, 2003). Among all types, the [FeFe]-hydrogenases ([FeFe]Hases) are most efficient (Cammack, 1999). The resemblance in structures between the [FeFe]Hase active site and the well known iron-sulfur-carbonyl complexes (Liu & Xiao, 2011; Song et al., 2005; Yin et al., 2011) draws intensive attention to the chemistry of such complexes. The title compound was prepared to mimic structurally the active site of [FeFe]Hases. Herein we report its crystal structure.

In agreement with other reported diiron complexes (Liu & Yin, 2010), the Fe₂S₂ unit in the title compound is in a butterfly conformation and each iron atom is coordinated with a pseudo-square-pyramidal geometry (Fig. 1). The deviation of Fe1 atom from the 2S2C-formed basal plane is 0.362 Å. The Fe—Fe distance of 2.4970 (6) Å in the title compound (Table 1) is enlarged by ca 0.03 Å than that found in [Fe₂(µ-C₄H₂H₂)(CO)₆] (Durgaprasad et al., 2011), indicating the strong electron-donating ability of the PMe₃ ligand. The Fe—P distance of 2.2450 (9) Å is in good agreement with those in the phosphane-coordinated diiron compounds (Li et al., 2005). The rigid dithiolate bridge is a special feature for the title compound. The calculated plane of the –SC₄H₂N₂S– bridge is nearly a bisect plane of the molecule. The angle between the Fe—Fe bond and the normal of the pyrazine-2,3-dithiolate plane is 2.78 (1)°.

Related literature top

The title compound was prepared as a biomimetic model of the [FeFe]-hydrogenase active site. For general background to hydrogenases and iron–sulfur–carbonyl complexes, see: Cammack (1999); Evans & Pickett (2003); Liu & Xiao (2011); Song et al. (2005); Yin et al. (2011). For related structures, see: Li et al. (2005); Liu & Yin (2010). For the synthesis, see: Durgaprasad et al. (2011).

Experimental top

All reactions and operations related to the title compound were carried out under a dry, prepurified nitrogen atmosphere with standard Schlenk techniques. All solvents were dried and distilled prior to use according to standard methods. Me₃NO and trimethylphosphane were available commercially and used without further purification. The starting material [Fe₂(µ-C₄H₂N₂)(CO)₆] was prepared according to the literature procedure (Durgaprasad et al., 2011). [Fe₂(µ-C₄H₂N₂)(CO)₆] (0.42 g, 1.0 mmol) and trimethylphosphane (0.08 g, 1.0 mmol) were reacted in CH₃CN (20 ml) in the presence of Me₃NO for 20 min at room temperature. The solvent was allowed to evaporate on a rotary evaporator to give a dark-red solid. The crude product was purified by column chromatography on Al₂O₃ using CH₂Cl₂/hexane as eluent to give a red solid (yield: 0.04 g, 10%). Recrystallization in a CH₂Cl₂/pentane solution afforded crystals of the title compound suitable for X-ray study.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 the 30% probability level.

Pentacarbonyl-1κ²C,2κ³C-(µ-pyrazine-2,3-dithiolato- 1:2κ⁴S,S':S,S')(trimethylphosphane- 1κP)diiron(I)(Fe—Fe) top

Crystal data top

[Fe₂(C₄H₂N₂S₂)(C₃H₉P)(CO)₅]	F(000) = 1888
M_r = 470.02	D_x = 1.743 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2383 reflections
a = 14.8307 (2) Å	θ = 2.4–21.5°
b = 12.1463 (2) Å	µ = 1.97 mm⁻¹
c = 19.8806 (3) Å	T = 273 K
V = 3581.25 (9) Å³	Block, red
Z = 8	0.10 × 0.10 × 0.10 mm

Data collection top

Bruker APEX CCD diffractometer	3327 independent reflections
Radiation source: fine-focus sealed tube	2445 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
φ and ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.828, T_max = 0.828	k = −12→14
19251 measured reflections	l = −24→23

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.034	w = 1/[σ²(F_o²) + (0.0259P)² + 0.3172P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.070	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.27 e Å⁻³
3327 reflections	Δρ_min = −0.32 e Å⁻³
217 parameters

Crystal data top

[Fe₂(C₄H₂N₂S₂)(C₃H₉P)(CO)₅]	V = 3581.25 (9) Å³
M_r = 470.02	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.8307 (2) Å	µ = 1.97 mm⁻¹
b = 12.1463 (2) Å	T = 273 K
c = 19.8806 (3) Å	0.10 × 0.10 × 0.10 mm

Data collection top

Bruker APEX CCD diffractometer	3327 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2445 reflections with I > 2σ(I)
T_min = 0.828, T_max = 0.828	R_int = 0.064
19251 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.01	Δρ_max = 0.27 e Å⁻³
3327 reflections	Δρ_min = −0.32 e Å⁻³
217 parameters

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

	x	y	z	U_iso*/U_eq
Fe2	0.03732 (3)	0.27229 (3)	0.07013 (2)	0.03067 (13)
Fe1	0.01883 (3)	0.18401 (4)	0.18272 (2)	0.03633 (14)
S2	0.01055 (5)	0.37018 (7)	0.16583 (4)	0.0357 (2)
S1	−0.09264 (5)	0.18655 (6)	0.10298 (4)	0.0365 (2)
P1	0.17667 (5)	0.34273 (7)	0.06048 (4)	0.0347 (2)
C11	0.1950 (2)	0.4175 (3)	−0.01705 (17)	0.0489 (9)
H11A	0.2555	0.4453	−0.0180	0.073*
H11B	0.1532	0.4778	−0.0197	0.073*
H11C	0.1858	0.3690	−0.0546	0.073*
C6	−0.10919 (19)	0.3860 (3)	0.16280 (15)	0.0343 (7)
N2	−0.14764 (17)	0.4745 (2)	0.18771 (14)	0.0444 (7)
C5	−0.0049 (2)	0.3498 (3)	0.00154 (18)	0.0383 (8)
N1	−0.24488 (17)	0.3034 (2)	0.12409 (14)	0.0457 (7)
C10	0.2693 (2)	0.2451 (3)	0.05956 (19)	0.0543 (10)
H10A	0.3253	0.2841	0.0553	0.081*
H10B	0.2623	0.1958	0.0222	0.081*
H10C	0.2693	0.2038	0.1007	0.081*
C7	−0.1565 (2)	0.3014 (3)	0.13199 (15)	0.0353 (8)
C1	−0.0420 (2)	0.1752 (3)	0.2611 (2)	0.0528 (10)
C3	0.1313 (2)	0.1954 (3)	0.21316 (18)	0.0466 (9)
C4	0.0725 (2)	0.1547 (3)	0.02547 (18)	0.0447 (9)
C9	−0.2385 (2)	0.4767 (3)	0.18021 (18)	0.0507 (10)
H9A	−0.2703	0.5367	0.1970	0.061*
C12	0.2126 (2)	0.4416 (3)	0.12345 (18)	0.0530 (10)
H12A	0.2729	0.4654	0.1137	0.080*
H12B	0.2111	0.4078	0.1671	0.080*
H12C	0.1728	0.5039	0.1229	0.080*
C2	0.0344 (2)	0.0406 (3)	0.16750 (17)	0.0478 (9)
C8	−0.2849 (2)	0.3953 (3)	0.14932 (19)	0.0522 (10)
H8A	−0.3471	0.4025	0.1451	0.063*
O5	−0.03314 (16)	0.3954 (2)	−0.04409 (13)	0.0617 (7)
O3	0.20369 (17)	0.2019 (2)	0.23081 (15)	0.0719 (9)
O4	0.09513 (17)	0.0780 (2)	−0.00373 (15)	0.0741 (9)
O2	0.04365 (18)	−0.0509 (2)	0.15663 (15)	0.0756 (9)
O1	−0.0802 (2)	0.1710 (3)	0.31047 (16)	0.0905 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe2	0.0309 (2)	0.0308 (3)	0.0303 (3)	−0.0002 (2)	0.00212 (19)	−0.0006 (2)
Fe1	0.0361 (3)	0.0381 (3)	0.0348 (3)	0.0003 (2)	0.0004 (2)	0.0057 (2)
S2	0.0333 (4)	0.0371 (5)	0.0366 (5)	−0.0017 (4)	0.0008 (3)	−0.0055 (4)
S1	0.0319 (4)	0.0358 (5)	0.0419 (5)	−0.0025 (4)	0.0002 (4)	−0.0044 (4)
P1	0.0294 (4)	0.0340 (5)	0.0406 (5)	0.0023 (4)	0.0032 (4)	0.0025 (4)
C11	0.042 (2)	0.048 (2)	0.057 (3)	−0.0001 (17)	0.0125 (17)	0.0151 (18)
C6	0.0349 (17)	0.0404 (19)	0.0275 (18)	0.0021 (16)	0.0011 (14)	0.0025 (15)
N2	0.0447 (17)	0.0452 (18)	0.0433 (18)	0.0106 (14)	−0.0005 (13)	−0.0074 (14)
C5	0.0347 (18)	0.040 (2)	0.040 (2)	−0.0022 (15)	−0.0006 (16)	−0.0049 (16)
N1	0.0300 (15)	0.059 (2)	0.0480 (19)	0.0030 (14)	−0.0002 (13)	−0.0056 (15)
C10	0.0390 (19)	0.054 (2)	0.070 (3)	0.0136 (17)	0.0019 (18)	0.0046 (19)
C7	0.0343 (18)	0.041 (2)	0.0307 (19)	0.0045 (15)	0.0025 (14)	0.0020 (15)
C1	0.051 (2)	0.057 (2)	0.050 (3)	0.0033 (19)	0.0052 (19)	0.0126 (19)
C3	0.051 (2)	0.042 (2)	0.046 (2)	0.0031 (18)	−0.0053 (18)	0.0098 (17)
C4	0.042 (2)	0.044 (2)	0.048 (2)	−0.0032 (17)	0.0117 (17)	−0.0020 (18)
C9	0.049 (2)	0.059 (3)	0.044 (2)	0.0245 (19)	−0.0006 (17)	−0.0078 (19)
C12	0.043 (2)	0.055 (2)	0.061 (3)	−0.0124 (18)	0.0046 (18)	−0.0097 (19)
C2	0.042 (2)	0.053 (3)	0.048 (2)	−0.0001 (18)	−0.0039 (17)	0.0102 (18)
C8	0.0300 (18)	0.072 (3)	0.054 (2)	0.0123 (19)	0.0010 (17)	−0.004 (2)
O5	0.0699 (18)	0.0627 (18)	0.0526 (18)	0.0014 (14)	−0.0212 (14)	0.0120 (14)
O3	0.0500 (16)	0.082 (2)	0.084 (2)	−0.0072 (14)	−0.0265 (15)	0.0217 (16)
O4	0.0776 (19)	0.0547 (18)	0.090 (2)	0.0011 (15)	0.0267 (16)	−0.0290 (16)
O2	0.083 (2)	0.0428 (18)	0.101 (2)	0.0090 (15)	−0.0070 (17)	−0.0054 (16)
O1	0.101 (2)	0.107 (3)	0.063 (2)	0.011 (2)	0.0383 (18)	0.0209 (18)

Geometric parameters (Å, º) top

Fe1—C1	1.803 (4)	C6—N2	1.314 (4)
Fe1—C2	1.784 (4)	C6—C7	1.387 (4)
Fe1—C3	1.780 (4)	N2—C9	1.356 (4)
Fe1—S1	2.2906 (9)	C5—O5	1.143 (4)
Fe1—S2	2.2893 (9)	N1—C7	1.320 (4)
Fe2—C4	1.761 (4)	N1—C8	1.360 (4)
Fe2—C5	1.771 (4)	C10—H10A	0.9600
Fe2—S1	2.2859 (9)	C10—H10B	0.9600
Fe2—S2	2.2783 (9)	C10—H10C	0.9600
Fe2—P1	2.2450 (9)	C1—O1	1.135 (4)
Fe2—Fe1	2.4970 (6)	C3—O3	1.132 (4)
S2—C6	1.787 (3)	C4—O4	1.148 (4)
S1—C7	1.782 (3)	C9—C8	1.352 (5)
P1—C11	1.809 (3)	C9—H9A	0.9300
P1—C10	1.815 (3)	C12—H12A	0.9600
P1—C12	1.815 (3)	C12—H12B	0.9600
C11—H11A	0.9600	C12—H12C	0.9600
C11—H11B	0.9600	C2—O2	1.139 (4)
C11—H11C	0.9600	C8—H8A	0.9300

C4—Fe2—C5	98.48 (16)	C10—P1—Fe2	116.66 (12)
C4—Fe2—P1	89.61 (11)	C12—P1—Fe2	117.62 (11)
C5—Fe2—P1	93.26 (10)	P1—C11—H11A	109.5
C4—Fe2—S2	153.63 (12)	P1—C11—H11B	109.5
C5—Fe2—S2	107.71 (11)	H11A—C11—H11B	109.5
P1—Fe2—S2	91.89 (3)	P1—C11—H11C	109.5
C4—Fe2—S1	91.40 (11)	H11A—C11—H11C	109.5
C5—Fe2—S1	99.45 (10)	H11B—C11—H11C	109.5
P1—Fe2—S1	166.96 (4)	N2—C6—C7	123.6 (3)
S2—Fe2—S1	81.51 (3)	N2—C6—S2	120.4 (2)
C4—Fe2—Fe1	97.83 (11)	C7—C6—S2	116.0 (2)
C5—Fe2—Fe1	151.59 (10)	C6—N2—C9	113.9 (3)
P1—Fe2—Fe1	109.96 (3)	O5—C5—Fe2	176.9 (3)
S2—Fe2—Fe1	57.07 (3)	C7—N1—C8	113.9 (3)
S1—Fe2—Fe1	57.02 (3)	P1—C10—H10A	109.5
C3—Fe1—C2	90.68 (15)	P1—C10—H10B	109.5
C3—Fe1—C1	100.37 (16)	H10A—C10—H10B	109.5
C2—Fe1—C1	98.81 (16)	P1—C10—H10C	109.5
C3—Fe1—S2	91.35 (11)	H10A—C10—H10C	109.5
C2—Fe1—S2	161.26 (11)	H10B—C10—H10C	109.5
C1—Fe1—S2	99.14 (12)	N1—C7—C6	122.7 (3)
C3—Fe1—S1	155.60 (12)	N1—C7—S1	120.3 (2)
C2—Fe1—S1	89.39 (11)	C6—C7—S1	117.0 (2)
C1—Fe1—S1	103.74 (12)	O1—C1—Fe1	179.1 (4)
S2—Fe1—S1	81.17 (3)	O3—C3—Fe1	178.1 (4)
C3—Fe1—Fe2	99.71 (11)	O4—C4—Fe2	179.7 (4)
C2—Fe1—Fe2	104.66 (11)	C8—C9—N2	122.8 (3)
C1—Fe1—Fe2	148.74 (11)	C8—C9—H9A	118.6
S2—Fe1—Fe2	56.65 (2)	N2—C9—H9A	118.6
S1—Fe1—Fe2	56.84 (2)	P1—C12—H12A	109.5
C6—S2—Fe2	101.60 (11)	P1—C12—H12B	109.5
C6—S2—Fe1	99.45 (11)	H12A—C12—H12B	109.5
Fe2—S2—Fe1	66.28 (3)	P1—C12—H12C	109.5
C7—S1—Fe2	100.61 (10)	H12A—C12—H12C	109.5
C7—S1—Fe1	99.80 (11)	H12B—C12—H12C	109.5
Fe2—S1—Fe1	66.13 (3)	O2—C2—Fe1	178.7 (3)
C11—P1—C10	101.87 (16)	C9—C8—N1	123.1 (3)
C11—P1—C12	102.21 (17)	C9—C8—H8A	118.5
C10—P1—C12	102.53 (16)	N1—C8—H8A	118.5
C11—P1—Fe2	113.71 (11)

C4—Fe2—Fe1—C3	86.09 (15)	C5—Fe2—S1—Fe1	−162.74 (11)
C5—Fe2—Fe1—C3	−149.4 (2)	P1—Fe2—S1—Fe1	4.13 (16)
P1—Fe2—Fe1—C3	−6.35 (12)	S2—Fe2—S1—Fe1	−56.06 (3)
S2—Fe2—Fe1—C3	−85.19 (12)	C3—Fe1—S1—C7	−115.1 (3)
S1—Fe2—Fe1—C3	172.66 (12)	C2—Fe1—S1—C7	154.63 (15)
C4—Fe2—Fe1—C2	−7.18 (15)	C1—Fe1—S1—C7	55.71 (16)
C5—Fe2—Fe1—C2	117.4 (2)	S2—Fe1—S1—C7	−41.61 (10)
P1—Fe2—Fe1—C2	−99.62 (11)	Fe2—Fe1—S1—C7	−97.35 (10)
S2—Fe2—Fe1—C2	−178.46 (11)	C3—Fe1—S1—Fe2	−17.7 (3)
S1—Fe2—Fe1—C2	79.39 (11)	C2—Fe1—S1—Fe2	−108.02 (11)
C4—Fe2—Fe1—C1	−144.6 (3)	C1—Fe1—S1—Fe2	153.05 (12)
C5—Fe2—Fe1—C1	−20.0 (3)	S2—Fe1—S1—Fe2	55.73 (3)
P1—Fe2—Fe1—C1	123.0 (2)	C4—Fe2—P1—C11	85.98 (17)
S2—Fe2—Fe1—C1	44.1 (2)	C5—Fe2—P1—C11	−12.49 (17)
S1—Fe2—Fe1—C1	−58.0 (2)	S2—Fe2—P1—C11	−120.35 (13)
C4—Fe2—Fe1—S2	171.28 (11)	S1—Fe2—P1—C11	−179.51 (18)
C5—Fe2—Fe1—S2	−64.2 (2)	Fe1—Fe2—P1—C11	−175.83 (13)
P1—Fe2—Fe1—S2	78.84 (4)	C4—Fe2—P1—C10	−32.18 (19)
S1—Fe2—Fe1—S2	−102.15 (3)	C5—Fe2—P1—C10	−130.65 (18)
C4—Fe2—Fe1—S1	−86.57 (11)	S2—Fe2—P1—C10	121.49 (14)
C5—Fe2—Fe1—S1	38.0 (2)	S1—Fe2—P1—C10	62.3 (2)
P1—Fe2—Fe1—S1	−179.01 (4)	Fe1—Fe2—P1—C10	66.01 (15)
S2—Fe2—Fe1—S1	102.15 (3)	C4—Fe2—P1—C12	−154.65 (18)
C4—Fe2—S2—C6	−115.1 (3)	C5—Fe2—P1—C12	106.88 (17)
C5—Fe2—S2—C6	57.96 (15)	S2—Fe2—P1—C12	−0.98 (14)
P1—Fe2—S2—C6	151.99 (11)	S1—Fe2—P1—C12	−60.1 (2)
S1—Fe2—S2—C6	−39.31 (11)	Fe1—Fe2—P1—C12	−56.46 (14)
Fe1—Fe2—S2—C6	−95.33 (11)	Fe2—S2—C6—N2	−147.9 (2)
C4—Fe2—S2—Fe1	−19.8 (2)	Fe1—S2—C6—N2	144.6 (2)
C5—Fe2—S2—Fe1	153.29 (10)	Fe2—S2—C6—C7	30.9 (2)
P1—Fe2—S2—Fe1	−112.68 (3)	Fe1—S2—C6—C7	−36.6 (2)
S1—Fe2—S2—Fe1	56.02 (3)	C7—C6—N2—C9	−0.5 (4)
C3—Fe1—S2—C6	−160.66 (15)	S2—C6—N2—C9	178.2 (2)
C2—Fe1—S2—C6	103.2 (4)	C8—N1—C7—C6	−0.5 (5)
C1—Fe1—S2—C6	−59.94 (16)	C8—N1—C7—S1	179.2 (2)
S1—Fe1—S2—C6	42.68 (11)	N2—C6—C7—N1	1.1 (5)
Fe2—Fe1—S2—C6	98.60 (11)	S2—C6—C7—N1	−177.7 (2)
C3—Fe1—S2—Fe2	100.74 (12)	N2—C6—C7—S1	−178.7 (2)
C2—Fe1—S2—Fe2	4.6 (3)	S2—C6—C7—S1	2.6 (3)
C1—Fe1—S2—Fe2	−158.53 (12)	Fe2—S1—C7—N1	145.7 (2)
S1—Fe1—S2—Fe2	−55.92 (3)	Fe1—S1—C7—N1	−146.9 (2)
C4—Fe2—S1—C7	−165.46 (16)	Fe2—S1—C7—C6	−34.5 (2)
C5—Fe2—S1—C7	−66.63 (15)	Fe1—S1—C7—C6	32.8 (2)
P1—Fe2—S1—C7	100.24 (18)	C6—N2—C9—C8	−0.5 (5)
S2—Fe2—S1—C7	40.04 (11)	N2—C9—C8—N1	1.1 (6)
Fe1—Fe2—S1—C7	96.11 (11)	C7—N1—C8—C9	−0.5 (5)
C4—Fe2—S1—Fe1	98.43 (12)

Experimental details

Crystal data
Chemical formula	[Fe₂(C₄H₂N₂S₂)(C₃H₉P)(CO)₅]
M_r	470.02
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	273
a, b, c (Å)	14.8307 (2), 12.1463 (2), 19.8806 (3)
V (Å³)	3581.25 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.828, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	19251, 3327, 2445
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.070, 1.01
No. of reflections	3327
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.32

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Fe1—C1	1.803 (4)	Fe2—C5	1.771 (4)
Fe1—C2	1.784 (4)	Fe2—S1	2.2859 (9)
Fe1—C3	1.780 (4)	Fe2—S2	2.2783 (9)
Fe1—S1	2.2906 (9)	Fe2—P1	2.2450 (9)
Fe1—S2	2.2893 (9)	Fe2—Fe1	2.4970 (6)
Fe2—C4	1.761 (4)

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Penta­carbonyl-1κ2C,2κ3C-(μ-pyrazine-2,3-dithiol­ato-1:2κ4S,S′:S,S′)(trimethyl­phosphane-1κP)diiron(I)(Fe—Fe)

Supporting information

Key indicators

checkCIF/PLATON results

Pentacarbonyl-1κ²C,2κ³C-(μ-pyrazine-2,3-dithiolato-1:2κ⁴S,S′:S,S′)(trimethylphosphane-1κP)diiron(I)(Fe—Fe)