Penta­carbonyl-1κ2C,2κ3C-(μ-ethyl 3-mercaptopropionato-1κS:2κS)(μ-4-methyl­benzoyl-1κO:2κC)(triphenyl­phosphine-1κP)diiron(Fe—Fe)

Liu, J.-T.; Du, Y.-C.; Mao, Y.-J.; Zhang, L.; Wu, Y.-L.

doi:10.1107/S1600536806006647

Pentacarbonyl-1κ²C,2κ³C-(μ-ethyl 3-mercaptopropionato-1κS:2κS)(μ-4-methylbenzoyl-1κO:2κC)(triphenylphosphine-1κP)diiron(Fe—Fe)

J.-T. Liu, Y.-C. Du, Y.-J. Mao, L. Zhang and Y.-L. Wu

In the molecule of the title compound, [Fe₂(C₈H₇O)(C₅H₉O₂S)(C₁₈H₁₅P)(CO)₅], the two Fe atoms are bridged by the ethyl 3-mercaptopropionate and 4-methylbenzoyl ligands. The central structural Fe₂COS fragment adopts an envelope conformation. Each Fe atom is in a pseudo-square pyramidal coordination. In addition, the crystal structure is stabilized by intermolecular C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006647/hk2004sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006647/hk2004Isup2.hkl Contains datablock I

CCDC reference: 601189

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.041
wR factor = 0.122
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.04
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C21    -   C22     ..       5.15 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C26    -   C27     ..       5.68 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C13     ..       6.34 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C26
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C32
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C35
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C19    -C24           1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C25    -C30           1.36 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C31    -C36           1.36 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         49
            C10 -FE2 -C9  -O3    111.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         50
            C11 -FE2 -C9  -O3   -151.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         51
            C1  -FE2 -C9  -O3     15.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         52
            S1  -FE2 -C9  -O3    -45.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         53
            FE1 -FE2 -C9  -O3    -53.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         54
            C9  -FE2 -C10 -O4      4.00  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 ... #         55
            C11 -FE2 -C10 -O4     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 ... #         56
            C1  -FE2 -C10 -O4      5.00  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 ... #         57
            S1  -FE2 -C10 -O4     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 ... #         58
            FE1 -FE2 -C10 -O4     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 ... #         59
            C9  -FE2 -C11 -O5     19.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         60
            C10 -FE2 -C11 -O5    123.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         61
            C1  -FE2 -C11 -O5    -61.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         62
            S1  -FE2 -C11 -O5   -134.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         63
            FE1 -FE2 -C11 -O5    -79.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         64
            C13 -FE1 -C12 -O2     40.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         65
            O1  -FE1 -C12 -O2   -132.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         66
            S1  -FE1 -C12 -O2    -63.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         67
            P1  -FE1 -C12 -O2    136.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         68
            FE2 -FE1 -C12 -O2    -60.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         69
            C12 -FE1 -C13 -O6    -70.00  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 ... #         70
            O1  -FE1 -C13 -O6     28.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         71
            S1  -FE1 -C13 -O6     85.00  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 ... #         72
            P1  -FE1 -C13 -O6   -169.00  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 ... #         73
            FE2 -FE1 -C13 -O6     29.00  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 ... #        103
            C13 -FE1 -O1  -C1     -3.40  0.80   1.555   1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc     -1.3(6), Rep     -1.4(2) ......       3.00 su-Rat
              C36 -C31 -C32 -C33    1.555   1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc     -1.8(7), Rep     -1.8(3) ......       2.33 su-Rat
              C31 -C32 -C33 -C34    1.555   1.555   1.555   1.555

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  18 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
  27 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-NT (Bruker, 1998); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Pentacarbonyl-1κ²C'2κ³C-(µ-ethyl 3-mercaptopropionato- 1κS:2κS)(µ-4-methylbenzoyl-1κO:2κC)(triphenylphosphine- 1κP)diiron(Fe—Fe) top

Crystal data top

[Fe₂(C₈H₇O)(C₅H₉O₂S)(C₁₈H₁₅P)(CO)₅]	Z = 2
M_r = 766.34	F(000) = 788
Triclinic, P1	D_x = 1.444 Mg m⁻³
a = 10.4846 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2367 (9) Å	Cell parameters from 6455 reflections
c = 16.7452 (13) Å	θ = 2.1–25.5°
α = 80.339 (1)°	µ = 0.98 mm⁻¹
β = 79.669 (1)°	T = 298 K
γ = 65.918 (1)°	Plate, dark red
V = 1762.0 (2) Å³	0.70 × 0.50 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6455 independent reflections
Radiation source: fine-focus sealed tube	5591 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
φ and ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→12
T_min = 0.548, T_max = 0.867	k = −13→13
9686 measured reflections	l = −17→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0759P)² + 0.4104P] where P = (F_o² + 2F_c²)/3
6455 reflections	(Δ/σ)_max = 0.001
435 parameters	Δρ_max = 0.71 e Å⁻³
28 restraints	Δρ_min = −0.35 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
Fe1	0.79168 (4)	0.96849 (4)	0.31214 (2)	0.03647 (13)
Fe2	0.84260 (4)	1.17542 (4)	0.26541 (2)	0.04125 (14)
C1	0.7915 (3)	1.1199 (3)	0.17518 (17)	0.0419 (6)
C2	0.7657 (3)	1.1843 (3)	0.09137 (18)	0.0459 (7)
C3	0.7768 (4)	1.1094 (3)	0.0302 (2)	0.0600 (9)
H3	0.8060	1.0189	0.0413	0.072*
C4	0.7447 (5)	1.1688 (4)	−0.0472 (2)	0.0686 (10)
H4	0.7548	1.1171	−0.0877	0.082*
C5	0.6979 (4)	1.3033 (4)	−0.0655 (2)	0.0607 (9)
C6	0.6597 (5)	1.3677 (5)	−0.1494 (2)	0.0854 (13)
H6A	0.5640	1.3820	−0.1526	0.128*
H6B	0.7210	1.3119	−0.1898	0.128*
H6C	0.6699	1.4502	−0.1591	0.128*
C7	0.6882 (4)	1.3768 (3)	−0.0044 (2)	0.0577 (8)
H7	0.6568	1.4675	−0.0153	0.069*
C8	0.7238 (3)	1.3188 (3)	0.07245 (19)	0.0501 (7)
H8	0.7197	1.3702	0.1117	0.060*
C9	0.6652 (4)	1.2899 (3)	0.2751 (2)	0.0544 (8)
C10	0.9369 (4)	1.2671 (3)	0.2025 (2)	0.0546 (8)
C11	0.8699 (3)	1.2017 (3)	0.3641 (2)	0.0531 (7)
C12	0.6056 (3)	1.0454 (3)	0.33596 (19)	0.0485 (7)
C13	0.8122 (3)	0.9491 (3)	0.41516 (19)	0.0467 (7)
C14	1.1279 (3)	0.9245 (3)	0.34294 (19)	0.0525 (7)
H14A	1.0740	0.9348	0.3967	0.063*
H14B	1.1915	0.8333	0.3419	0.063*
C15	1.2130 (3)	1.0092 (4)	0.3284 (2)	0.0562 (8)
H15A	1.1492	1.0995	0.3339	0.067*
H15B	1.2752	0.9822	0.3703	0.067*
C16	1.2996 (3)	1.0028 (3)	0.24646 (19)	0.0496 (7)
C17	1.3997 (5)	1.1239 (5)	0.1433 (2)	0.0777 (11)
H17A	1.3672	1.1023	0.0991	0.093*
H17B	1.4960	1.0630	0.1481	0.093*
C18	1.3914 (5)	1.2614 (5)	0.1271 (3)	0.0881 (13)
H18A	1.2945	1.3211	0.1303	0.132*
H18B	1.4382	1.2742	0.0735	0.132*
H18C	1.4363	1.2774	0.1670	0.132*
C19	0.6680 (3)	0.7180 (3)	0.36483 (18)	0.0445 (6)
C20	0.6310 (5)	0.6249 (4)	0.3437 (3)	0.0894 (13)
H20	0.6829	0.5785	0.2997	0.107*
C21	0.5188 (6)	0.5985 (6)	0.3861 (4)	0.1102 (17)
H21	0.4942	0.5364	0.3697	0.132*
C22	0.4436 (5)	0.6630 (4)	0.4518 (3)	0.0823 (13)
H22	0.3671	0.6459	0.4801	0.099*
C23	0.4806 (4)	0.7513 (3)	0.4755 (2)	0.0582 (8)
H23	0.4312	0.7934	0.5215	0.070*
C24	0.5914 (3)	0.7804 (3)	0.43226 (19)	0.0503 (7)
H24	0.6146	0.8431	0.4490	0.060*
C25	0.9687 (3)	0.6229 (3)	0.34024 (18)	0.0466 (6)
C26	1.0245 (6)	0.5103 (4)	0.3045 (3)	0.0990 (17)
H26	0.9850	0.5035	0.2609	0.119*
C27	1.1400 (6)	0.4043 (5)	0.3320 (4)	0.1104 (17)
H27	1.1756	0.3267	0.3077	0.132*
C28	1.2006 (4)	0.4139 (4)	0.3939 (3)	0.0787 (12)
H28	1.2757	0.3423	0.4138	0.094*
C29	1.1514 (5)	0.5278 (5)	0.4265 (3)	0.0935 (15)
H29	1.1963	0.5357	0.4672	0.112*
C30	1.0357 (4)	0.6338 (4)	0.4009 (3)	0.0746 (11)
H30	1.0032	0.7120	0.4243	0.089*
C31	0.8139 (3)	0.7376 (3)	0.20186 (18)	0.0449 (6)
C32	0.9345 (4)	0.7109 (4)	0.1493 (2)	0.0937 (17)
H32	1.0177	0.6974	0.1686	0.112*
C33	0.9357 (5)	0.7036 (5)	0.0676 (3)	0.0954 (14)
H33	1.0190	0.6876	0.0324	0.114*
C34	0.8182 (5)	0.7193 (5)	0.0387 (2)	0.0973 (16)
H34	0.8205	0.7087	−0.0156	0.117*
C35	0.6977 (5)	0.7503 (5)	0.0887 (3)	0.1037 (18)
H35	0.6148	0.7660	0.0683	0.124*
C36	0.6940 (4)	0.7595 (4)	0.1703 (2)	0.0788 (13)
H36	0.6089	0.7808	0.2042	0.095*
O1	0.7745 (2)	1.01418 (19)	0.19277 (11)	0.0442 (4)
O2	0.4879 (2)	1.0982 (3)	0.35448 (18)	0.0754 (7)
O3	0.5510 (3)	1.3620 (3)	0.28038 (19)	0.0816 (8)
O4	0.9958 (3)	1.3253 (3)	0.16250 (18)	0.0851 (9)
O5	0.8815 (3)	1.2200 (3)	0.42652 (16)	0.0815 (8)
O6	0.8242 (3)	0.9414 (3)	0.48293 (14)	0.0734 (7)
O7	1.3543 (3)	0.9090 (3)	0.20980 (17)	0.0735 (7)
O8	1.3097 (3)	1.1162 (3)	0.21960 (15)	0.0662 (6)
P1	0.81204 (7)	0.76128 (7)	0.30698 (4)	0.03733 (17)
S1	1.00725 (7)	0.96718 (7)	0.26616 (4)	0.04046 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0363 (2)	0.0412 (2)	0.0335 (2)	−0.01607 (17)	−0.00595 (16)	−0.00374 (16)
Fe2	0.0460 (2)	0.0422 (2)	0.0394 (2)	−0.01932 (19)	−0.00783 (17)	−0.00627 (17)
C1	0.0396 (14)	0.0447 (15)	0.0407 (15)	−0.0150 (12)	−0.0063 (11)	−0.0050 (12)
C2	0.0487 (16)	0.0492 (16)	0.0418 (15)	−0.0211 (13)	−0.0114 (13)	0.0010 (12)
C3	0.086 (3)	0.0497 (17)	0.0455 (18)	−0.0256 (17)	−0.0199 (17)	0.0007 (14)
C4	0.100 (3)	0.070 (2)	0.0418 (18)	−0.035 (2)	−0.0219 (19)	−0.0022 (16)
C5	0.065 (2)	0.071 (2)	0.0464 (18)	−0.0294 (18)	−0.0167 (15)	0.0125 (16)
C6	0.108 (3)	0.092 (3)	0.058 (2)	−0.042 (3)	−0.036 (2)	0.022 (2)
C7	0.062 (2)	0.0505 (17)	0.058 (2)	−0.0227 (15)	−0.0148 (16)	0.0110 (15)
C8	0.0569 (18)	0.0491 (16)	0.0473 (17)	−0.0235 (14)	−0.0104 (14)	−0.0009 (13)
C9	0.059 (2)	0.0511 (17)	0.0526 (19)	−0.0153 (16)	−0.0128 (15)	−0.0140 (14)
C10	0.064 (2)	0.0592 (18)	0.0519 (18)	−0.0339 (17)	−0.0098 (15)	−0.0059 (15)
C11	0.0527 (18)	0.0580 (18)	0.0500 (18)	−0.0189 (15)	−0.0071 (14)	−0.0160 (15)
C12	0.0437 (17)	0.0523 (17)	0.0517 (18)	−0.0195 (14)	−0.0104 (13)	−0.0042 (14)
C13	0.0421 (15)	0.0549 (17)	0.0429 (17)	−0.0187 (13)	−0.0051 (12)	−0.0057 (13)
C14	0.0409 (15)	0.071 (2)	0.0448 (16)	−0.0224 (15)	−0.0101 (13)	0.0014 (14)
C15	0.0449 (16)	0.083 (2)	0.0480 (18)	−0.0293 (16)	−0.0051 (14)	−0.0144 (16)
C16	0.0363 (14)	0.065 (2)	0.0514 (17)	−0.0213 (14)	−0.0080 (13)	−0.0092 (15)
C17	0.076 (3)	0.095 (3)	0.061 (2)	−0.042 (2)	0.0018 (19)	0.004 (2)
C18	0.092 (3)	0.105 (3)	0.087 (3)	−0.061 (3)	−0.025 (3)	0.013 (3)
C19	0.0454 (15)	0.0402 (14)	0.0453 (16)	−0.0171 (12)	0.0017 (12)	−0.0043 (12)
C20	0.106 (3)	0.084 (2)	0.095 (3)	−0.063 (2)	0.043 (2)	−0.042 (2)
C21	0.127 (3)	0.112 (3)	0.122 (3)	−0.086 (3)	0.037 (3)	−0.047 (2)
C22	0.081 (3)	0.095 (3)	0.087 (3)	−0.060 (2)	0.035 (2)	−0.030 (2)
C23	0.0563 (19)	0.0601 (19)	0.0549 (19)	−0.0246 (16)	0.0098 (15)	−0.0097 (15)
C24	0.0520 (17)	0.0559 (17)	0.0461 (17)	−0.0259 (15)	0.0023 (13)	−0.0093 (13)
C25	0.0417 (15)	0.0439 (15)	0.0452 (15)	−0.0089 (12)	−0.0025 (11)	−0.0045 (12)
C26	0.102 (4)	0.065 (3)	0.114 (4)	0.006 (2)	−0.051 (3)	−0.028 (2)
C27	0.109 (3)	0.084 (3)	0.116 (3)	−0.006 (2)	−0.024 (3)	−0.026 (2)
C28	0.058 (2)	0.063 (2)	0.091 (3)	−0.0008 (18)	−0.017 (2)	0.005 (2)
C29	0.082 (3)	0.076 (3)	0.127 (4)	−0.026 (2)	−0.054 (3)	0.007 (3)
C30	0.080 (3)	0.057 (2)	0.094 (3)	−0.0237 (19)	−0.041 (2)	−0.0026 (19)
C31	0.0437 (15)	0.0519 (16)	0.0393 (15)	−0.0174 (13)	−0.0059 (12)	−0.0074 (12)
C32	0.053 (2)	0.185 (5)	0.047 (2)	−0.047 (3)	0.0020 (17)	−0.028 (3)
C33	0.078 (2)	0.142 (3)	0.061 (2)	−0.038 (2)	0.0049 (19)	−0.024 (2)
C34	0.085 (3)	0.168 (5)	0.046 (2)	−0.049 (3)	−0.008 (2)	−0.030 (3)
C35	0.072 (3)	0.176 (5)	0.065 (3)	−0.035 (3)	−0.023 (2)	−0.037 (3)
C36	0.0469 (19)	0.127 (4)	0.060 (2)	−0.021 (2)	−0.0057 (16)	−0.037 (2)
O1	0.0559 (12)	0.0451 (11)	0.0374 (10)	−0.0239 (9)	−0.0139 (9)	0.0001 (8)
O2	0.0404 (14)	0.0805 (17)	0.096 (2)	−0.0133 (12)	−0.0045 (13)	−0.0159 (15)
O3	0.0618 (16)	0.0738 (17)	0.092 (2)	0.0003 (14)	−0.0161 (15)	−0.0276 (15)
O4	0.103 (2)	0.099 (2)	0.0777 (18)	−0.0711 (19)	−0.0105 (16)	0.0070 (16)
O5	0.0821 (19)	0.108 (2)	0.0583 (16)	−0.0288 (16)	−0.0121 (14)	−0.0377 (15)
O6	0.0814 (18)	0.104 (2)	0.0362 (13)	−0.0358 (16)	−0.0103 (12)	−0.0076 (12)
O7	0.0618 (15)	0.0742 (17)	0.0827 (18)	−0.0282 (13)	0.0162 (13)	−0.0260 (14)
O8	0.0657 (15)	0.0720 (15)	0.0637 (15)	−0.0329 (13)	0.0027 (12)	−0.0102 (12)
P1	0.0362 (4)	0.0399 (4)	0.0346 (4)	−0.0138 (3)	−0.0027 (3)	−0.0049 (3)
S1	0.0362 (3)	0.0482 (4)	0.0373 (4)	−0.0168 (3)	−0.0040 (3)	−0.0051 (3)

Geometric parameters (Å, º) top

Fe1—C13	1.743 (3)	C17—C18	1.493 (6)
Fe1—C12	1.782 (3)	C17—H17A	0.9700
Fe1—O1	2.0001 (19)	C17—H17B	0.9700
Fe1—S1	2.2481 (8)	C18—H18A	0.9600
Fe1—P1	2.2648 (8)	C18—H18B	0.9600
Fe1—Fe2	2.5606 (6)	C18—H18C	0.9600
Fe2—C9	1.775 (3)	C19—C20	1.369 (5)
Fe2—C10	1.801 (3)	C19—C24	1.376 (4)
Fe2—C11	1.818 (3)	C19—P1	1.836 (3)
Fe2—C1	1.959 (3)	C20—C21	1.375 (6)
Fe2—S1	2.2709 (8)	C20—H20	0.9300
C1—O1	1.252 (3)	C21—C22	1.359 (6)
C1—C2	1.484 (4)	C21—H21	0.9300
C2—C8	1.388 (4)	C22—C23	1.339 (5)
C2—C3	1.392 (5)	C22—H22	0.9300
C3—C4	1.386 (5)	C23—C24	1.383 (4)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.383 (5)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.351 (5)
C5—C7	1.384 (5)	C25—C30	1.381 (5)
C5—C6	1.511 (5)	C25—P1	1.838 (3)
C6—H6A	0.9600	C26—C27	1.392 (7)
C6—H6B	0.9600	C26—H26	0.9300
C6—H6C	0.9600	C27—C28	1.349 (7)
C7—C8	1.383 (4)	C27—H27	0.9300
C7—H7	0.9300	C28—C29	1.340 (6)
C8—H8	0.9300	C28—H28	0.9300
C9—O3	1.137 (4)	C29—C30	1.382 (6)
C10—O4	1.136 (4)	C29—H29	0.9300
C11—O5	1.134 (4)	C30—H30	0.9300
C12—O2	1.139 (4)	C31—C32	1.358 (5)
C13—O6	1.149 (4)	C31—C36	1.364 (5)
C14—C15	1.517 (5)	C31—P1	1.819 (3)
C14—S1	1.834 (3)	C32—C33	1.382 (6)
C14—H14A	0.9700	C32—H32	0.9300
C14—H14B	0.9700	C33—C34	1.339 (7)
C15—C16	1.498 (4)	C33—H33	0.9300
C15—H15A	0.9700	C34—C35	1.334 (6)
C15—H15B	0.9700	C34—H34	0.9300
C16—O7	1.190 (4)	C35—C36	1.380 (6)
C16—O8	1.319 (4)	C35—H35	0.9300
C17—O8	1.459 (4)	C36—H36	0.9300

C13—Fe1—C12	90.44 (14)	O8—C17—C18	106.8 (4)
C13—Fe1—O1	171.55 (12)	O8—C17—H17A	110.4
C12—Fe1—O1	90.71 (12)	C18—C17—H17A	110.4
C13—Fe1—S1	95.08 (10)	O8—C17—H17B	110.4
C12—Fe1—S1	154.12 (10)	C18—C17—H17B	110.4
O1—Fe1—S1	80.36 (6)	H17A—C17—H17B	108.6
C13—Fe1—P1	96.22 (11)	C17—C18—H18A	109.5
C12—Fe1—P1	99.36 (10)	C17—C18—H18B	109.5
O1—Fe1—P1	91.85 (6)	H18A—C18—H18B	109.5
S1—Fe1—P1	105.13 (3)	C17—C18—H18C	109.5
C13—Fe1—Fe2	99.64 (10)	H18A—C18—H18C	109.5
C12—Fe1—Fe2	98.25 (10)	H18B—C18—H18C	109.5
O1—Fe1—Fe2	71.92 (6)	C20—C19—C24	117.1 (3)
S1—Fe1—Fe2	55.90 (2)	C20—C19—P1	122.8 (3)
P1—Fe1—Fe2	156.13 (3)	C24—C19—P1	120.2 (2)
C9—Fe2—C10	103.87 (16)	C19—C20—C21	121.5 (4)
C9—Fe2—C11	92.43 (14)	C19—C20—H20	119.3
C10—Fe2—C11	97.79 (15)	C21—C20—H20	119.3
C9—Fe2—C1	85.28 (13)	C22—C21—C20	120.2 (4)
C10—Fe2—C1	96.08 (13)	C22—C21—H21	119.9
C11—Fe2—C1	166.09 (14)	C20—C21—H21	119.9
C9—Fe2—S1	151.81 (12)	C23—C22—C21	119.6 (4)
C10—Fe2—S1	101.89 (12)	C23—C22—H22	120.2
C11—Fe2—S1	95.24 (11)	C21—C22—H22	120.2
C1—Fe2—S1	80.81 (8)	C22—C23—C24	120.6 (3)
C9—Fe2—Fe1	97.07 (12)	C22—C23—H23	119.7
C10—Fe2—Fe1	153.43 (11)	C24—C23—H23	119.7
C11—Fe2—Fe1	97.47 (11)	C19—C24—C23	121.0 (3)
C1—Fe2—Fe1	69.28 (9)	C19—C24—H24	119.5
S1—Fe2—Fe1	55.07 (2)	C23—C24—H24	119.5
O1—C1—C2	115.5 (2)	C26—C25—C30	118.2 (3)
O1—C1—Fe2	113.7 (2)	C26—C25—P1	121.5 (3)
C2—C1—Fe2	130.8 (2)	C30—C25—P1	120.3 (3)
C8—C2—C3	118.3 (3)	C25—C26—C27	121.1 (5)
C8—C2—C1	122.0 (3)	C25—C26—H26	119.5
C3—C2—C1	119.6 (3)	C27—C26—H26	119.5
C4—C3—C2	120.4 (3)	C28—C27—C26	120.1 (5)
C4—C3—H3	119.8	C28—C27—H27	119.9
C2—C3—H3	119.8	C26—C27—H27	119.9
C5—C4—C3	121.4 (3)	C29—C28—C27	119.3 (4)
C5—C4—H4	119.3	C29—C28—H28	120.4
C3—C4—H4	119.3	C27—C28—H28	120.4
C4—C5—C7	117.7 (3)	C28—C29—C30	121.6 (4)
C4—C5—C6	121.1 (4)	C28—C29—H29	119.2
C7—C5—C6	121.2 (3)	C30—C29—H29	119.2
C5—C6—H6A	109.5	C25—C30—C29	119.5 (4)
C5—C6—H6B	109.5	C25—C30—H30	120.2
H6A—C6—H6B	109.5	C29—C30—H30	120.2
C5—C6—H6C	109.5	C32—C31—C36	117.3 (3)
H6A—C6—H6C	109.5	C32—C31—P1	120.1 (3)
H6B—C6—H6C	109.5	C36—C31—P1	122.2 (3)
C8—C7—C5	121.6 (3)	C31—C32—C33	121.1 (4)
C8—C7—H7	119.2	C31—C32—H32	119.4
C5—C7—H7	119.2	C33—C32—H32	119.4
C7—C8—C2	120.4 (3)	C34—C33—C32	120.6 (4)
C7—C8—H8	119.8	C34—C33—H33	119.7
C2—C8—H8	119.8	C32—C33—H33	119.7
O3—C9—Fe2	178.7 (3)	C35—C34—C33	119.1 (4)
O4—C10—Fe2	179.6 (4)	C35—C34—H34	120.5
O5—C11—Fe2	177.4 (3)	C33—C34—H34	120.5
O2—C12—Fe1	175.9 (3)	C34—C35—C36	121.1 (4)
O6—C13—Fe1	177.4 (3)	C34—C35—H35	119.5
C15—C14—S1	112.2 (2)	C36—C35—H35	119.5
C15—C14—H14A	109.2	C31—C36—C35	120.7 (4)
S1—C14—H14A	109.2	C31—C36—H36	119.6
C15—C14—H14B	109.2	C35—C36—H36	119.6
S1—C14—H14B	109.2	C1—O1—Fe1	104.78 (17)
H14A—C14—H14B	107.9	C16—O8—C17	117.8 (3)
C16—C15—C14	114.1 (3)	C31—P1—C19	105.00 (14)
C16—C15—H15A	108.7	C31—P1—C25	103.97 (13)
C14—C15—H15A	108.7	C19—P1—C25	102.24 (14)
C16—C15—H15B	108.7	C31—P1—Fe1	109.23 (9)
C14—C15—H15B	108.7	C19—P1—Fe1	115.77 (9)
H15A—C15—H15B	107.6	C25—P1—Fe1	119.16 (11)
O7—C16—O8	123.4 (3)	C14—S1—Fe1	116.37 (10)
O7—C16—C15	125.7 (3)	C14—S1—Fe2	113.65 (12)
O8—C16—C15	110.8 (3)	Fe1—S1—Fe2	69.03 (2)

C13—Fe1—Fe2—C9	−94.96 (14)	P1—C19—C24—C23	178.5 (3)
C12—Fe1—Fe2—C9	−3.11 (14)	C22—C23—C24—C19	−1.2 (6)
O1—Fe1—Fe2—C9	84.93 (12)	C30—C25—C26—C27	4.8 (8)
S1—Fe1—Fe2—C9	175.41 (11)	P1—C25—C26—C27	−177.7 (5)
P1—Fe1—Fe2—C9	134.08 (12)	C25—C26—C27—C28	−1.7 (10)
C13—Fe1—Fe2—C10	123.0 (3)	C26—C27—C28—C29	−2.4 (9)
C12—Fe1—Fe2—C10	−145.1 (3)	C27—C28—C29—C30	3.2 (8)
O1—Fe1—Fe2—C10	−57.1 (2)	C26—C25—C30—C29	−3.9 (7)
S1—Fe1—Fe2—C10	33.4 (2)	P1—C25—C30—C29	178.5 (4)
P1—Fe1—Fe2—C10	−7.9 (3)	C28—C29—C30—C25	−0.1 (8)
C13—Fe1—Fe2—C11	−1.56 (14)	C36—C31—C32—C33	−1.4 (2)
C12—Fe1—Fe2—C11	90.30 (15)	P1—C31—C32—C33	−174.5 (2)
O1—Fe1—Fe2—C11	178.34 (12)	C31—C32—C33—C34	−1.8 (3)
S1—Fe1—Fe2—C11	−91.18 (11)	C32—C33—C34—C35	4.2 (6)
P1—Fe1—Fe2—C11	−132.51 (12)	C33—C34—C35—C36	−3.5 (7)
C13—Fe1—Fe2—C1	−177.17 (13)	C32—C31—C36—C35	2.1 (5)
C12—Fe1—Fe2—C1	−85.31 (13)	P1—C31—C36—C35	175.0 (3)
O1—Fe1—Fe2—C1	2.73 (11)	C34—C35—C36—C31	0.3 (7)
S1—Fe1—Fe2—C1	93.21 (9)	C2—C1—O1—Fe1	−172.6 (2)
P1—Fe1—Fe2—C1	51.88 (11)	Fe2—C1—O1—Fe1	5.6 (2)
C13—Fe1—Fe2—S1	89.62 (10)	C13—Fe1—O1—C1	−3.4 (8)
C12—Fe1—Fe2—S1	−178.52 (10)	C12—Fe1—O1—C1	94.3 (2)
O1—Fe1—Fe2—S1	−90.48 (7)	S1—Fe1—O1—C1	−61.26 (17)
P1—Fe1—Fe2—S1	−41.33 (6)	P1—Fe1—O1—C1	−166.30 (17)
C9—Fe2—C1—O1	−103.9 (2)	Fe2—Fe1—O1—C1	−4.13 (16)
C10—Fe2—C1—O1	152.6 (2)	O7—C16—O8—C17	−3.7 (5)
C11—Fe2—C1—O1	−22.9 (7)	C15—C16—O8—C17	175.4 (3)
S1—Fe2—C1—O1	51.5 (2)	C18—C17—O8—C16	179.7 (3)
Fe1—Fe2—C1—O1	−4.53 (18)	C32—C31—P1—C19	−154.3 (2)
C9—Fe2—C1—C2	73.9 (3)	C36—C31—P1—C19	32.9 (3)
C10—Fe2—C1—C2	−29.5 (3)	C32—C31—P1—C25	−47.3 (2)
C11—Fe2—C1—C2	154.9 (5)	C36—C31—P1—C25	139.9 (3)
S1—Fe2—C1—C2	−130.7 (3)	C32—C31—P1—Fe1	80.9 (2)
Fe1—Fe2—C1—C2	173.3 (3)	C36—C31—P1—Fe1	−91.8 (3)
O1—C1—C2—C8	153.2 (3)	C20—C19—P1—C31	31.6 (4)
Fe2—C1—C2—C8	−24.6 (4)	C24—C19—P1—C31	−147.9 (3)
O1—C1—C2—C3	−23.5 (4)	C20—C19—P1—C25	−76.7 (4)
Fe2—C1—C2—C3	158.7 (3)	C24—C19—P1—C25	103.8 (3)
C8—C2—C3—C4	−0.9 (5)	C20—C19—P1—Fe1	152.2 (3)
C1—C2—C3—C4	176.0 (3)	C24—C19—P1—Fe1	−27.4 (3)
C2—C3—C4—C5	−1.5 (6)	C26—C25—P1—C31	−24.6 (4)
C3—C4—C5—C7	1.9 (6)	C30—C25—P1—C31	152.9 (3)
C3—C4—C5—C6	−178.5 (4)	C26—C25—P1—C19	84.5 (4)
C4—C5—C7—C8	0.1 (6)	C30—C25—P1—C19	−98.0 (3)
C6—C5—C7—C8	−179.5 (4)	C26—C25—P1—Fe1	−146.4 (4)
C5—C7—C8—C2	−2.5 (5)	C30—C25—P1—Fe1	31.1 (3)
C3—C2—C8—C7	2.8 (5)	C13—Fe1—P1—C31	−174.10 (14)
C1—C2—C8—C7	−174.0 (3)	C12—Fe1—P1—C31	94.42 (14)
C10—Fe2—C9—O3	111 (17)	O1—Fe1—P1—C31	3.40 (12)
C11—Fe2—C9—O3	−151 (17)	S1—Fe1—P1—C31	−77.11 (10)
C1—Fe2—C9—O3	15 (17)	Fe2—Fe1—P1—C31	−42.61 (12)
S1—Fe2—C9—O3	−45 (17)	C13—Fe1—P1—C19	67.68 (15)
Fe1—Fe2—C9—O3	−53 (17)	C12—Fe1—P1—C19	−23.79 (15)
C9—Fe2—C10—O4	−37 (58)	O1—Fe1—P1—C19	−114.81 (13)
C11—Fe2—C10—O4	−131 (58)	S1—Fe1—P1—C19	164.67 (11)
C1—Fe2—C10—O4	50 (58)	Fe2—Fe1—P1—C19	−160.82 (11)
S1—Fe2—C10—O4	132 (100)	C13—Fe1—P1—C25	−54.92 (15)
Fe1—Fe2—C10—O4	104 (58)	C12—Fe1—P1—C25	−146.40 (15)
C9—Fe2—C11—O5	19 (7)	O1—Fe1—P1—C25	122.58 (13)
C10—Fe2—C11—O5	123 (7)	S1—Fe1—P1—C25	42.07 (12)
C1—Fe2—C11—O5	−61 (7)	Fe2—Fe1—P1—C25	76.57 (13)
S1—Fe2—C11—O5	−134 (7)	C15—C14—S1—Fe1	−139.4 (2)
Fe1—Fe2—C11—O5	−79 (7)	C15—C14—S1—Fe2	−62.1 (3)
C13—Fe1—C12—O2	40 (4)	C13—Fe1—S1—C14	8.61 (17)
O1—Fe1—C12—O2	−132 (4)	C12—Fe1—S1—C14	110.2 (3)
S1—Fe1—C12—O2	−63 (4)	O1—Fe1—S1—C14	−178.56 (14)
P1—Fe1—C12—O2	136 (4)	P1—Fe1—S1—C14	−89.24 (13)
Fe2—Fe1—C12—O2	−60 (4)	Fe2—Fe1—S1—C14	106.83 (13)
C12—Fe1—C13—O6	−70 (6)	C13—Fe1—S1—Fe2	−98.21 (10)
O1—Fe1—C13—O6	28 (7)	C12—Fe1—S1—Fe2	3.4 (2)
S1—Fe1—C13—O6	85 (6)	O1—Fe1—S1—Fe2	74.62 (6)
P1—Fe1—C13—O6	−169 (6)	P1—Fe1—S1—Fe2	163.93 (3)
Fe2—Fe1—C13—O6	29 (6)	C9—Fe2—S1—C14	−120.2 (3)
S1—C14—C15—C16	−58.1 (3)	C10—Fe2—S1—C14	84.01 (15)
C14—C15—C16—O7	−33.8 (5)	C11—Fe2—S1—C14	−15.11 (16)
C14—C15—C16—O8	147.1 (3)	C1—Fe2—S1—C14	178.34 (14)
C24—C19—C20—C21	2.4 (7)	Fe1—Fe2—S1—C14	−110.57 (11)
P1—C19—C20—C21	−177.2 (5)	C9—Fe2—S1—Fe1	−9.7 (2)
C19—C20—C21—C22	−1.6 (9)	C10—Fe2—S1—Fe1	−165.42 (11)
C20—C21—C22—C23	−0.7 (9)	C11—Fe2—S1—Fe1	95.47 (11)
C21—C22—C23—C24	2.1 (7)	C1—Fe2—S1—Fe1	−71.09 (9)
C20—C19—C24—C23	−1.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O3ⁱ	0.93	2.48	3.308 (6)	149
C36—H36···O7ⁱⁱ	0.93	2.45	3.254 (5)	144

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z.

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Penta­carbonyl-1κ2C,2κ3C-(μ-ethyl 3-mercaptopropionato-1κS:2κS)(μ-4-methyl­benzoyl-1κO:2κC)(triphenyl­phosphine-1κP)diiron(Fe—Fe)

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Pentacarbonyl-1κ²C,2κ³C-(μ-ethyl 3-mercaptopropionato-1κS:2κS)(μ-4-methylbenzoyl-1κO:2κC)(triphenylphosphine-1κP)diiron(Fe—Fe)