



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808032698/ci2685sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808032698/ci2685Isup2.hkl |
CCDC reference: 709668
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.048
- wR factor = 0.079
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level C Value of measurement temperature given = 298.000 Value of melting point given = 0.000 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 -- C14 .. 5.46 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe2 -- C10 .. 7.20 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe2 -- C11 .. 5.66 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 5 Informative message, check
The starting material [Fe2(µ-SCH2)2(4-CH3C6H4N)(CO)6] was obtained in 50% yield according to the literature method (Hou et al., 2006). The solution of Me3NO (120 mg, 1.06 mmol) was added to a red solution of [Fe2(µ-SCH2)2(4-CH3C6H4N)(CO)6] (0.50 g, 1.05 mmol) with FcPPh2 (0.39 g, 1.05 mmol) in CH3CN (100 ml) via syringe under a nitrogen atmosphere. The reaction mixture was stirred at ambient temperature until the TLC indicated there was no remaining carbonyl complex of starting material. The solvent was removed under vacuum and the resulted dark red residue was purified by column chromatography on silica gel eluting with CH2Cl2-hexane (1:5 v/v). A dark red solid was obtained from recrystallization in n-pentane-CH2Cl2. Single crystals of the title compound for X-ray analysis were grown from a CH2Cl2-hexane (1:5 v/v) solution by slow evaporation at ambient temperature.
H atoms were placed in geometrically calculated positions (C—H = 0.93–0.98 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl)
Data collection: SMART (Bruker, 1997); 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: SHELXL97 (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of the title complex, with displacement ellipsoids drawn at the 30% probability level. |
[Fe3(C5H5)(C9H11NS2)(C17H14P)(CO)5] | F(000) = 1672 |
Mr = 819.25 | Dx = 1.575 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2549 reflections |
a = 13.600 (2) Å | θ = 2.4–22.0° |
b = 10.8964 (19) Å | µ = 1.45 mm−1 |
c = 23.396 (4) Å | T = 298 K |
β = 94.741 (3)° | Block, red |
V = 3455.2 (11) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 8202 independent reflections |
Radiation source: fine-focus sealed tube | 4258 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
ϕ and ω scans | θmax = 28.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −17→18 |
Tmin = 0.760, Tmax = 0.868 | k = −9→14 |
21457 measured reflections | l = −31→30 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0157P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max = 0.001 |
S = 0.80 | Δρmax = 0.66 e Å−3 |
8202 reflections | Δρmin = −0.39 e Å−3 |
434 parameters |
[Fe3(C5H5)(C9H11NS2)(C17H14P)(CO)5] | V = 3455.2 (11) Å3 |
Mr = 819.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.600 (2) Å | µ = 1.45 mm−1 |
b = 10.8964 (19) Å | T = 298 K |
c = 23.396 (4) Å | 0.20 × 0.20 × 0.10 mm |
β = 94.741 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 8202 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 4258 reflections with I > 2σ(I) |
Tmin = 0.760, Tmax = 0.868 | Rint = 0.070 |
21457 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.80 | Δρmax = 0.66 e Å−3 |
8202 reflections | Δρmin = −0.39 e Å−3 |
434 parameters |
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.20737 (4) | 0.18453 (5) | 0.30929 (2) | 0.03252 (14) | |
Fe2 | 0.20176 (4) | 0.09491 (5) | 0.40808 (2) | 0.03988 (16) | |
Fe3 | 0.08083 (4) | 0.09519 (5) | 0.11522 (2) | 0.04244 (16) | |
S1 | 0.34466 (7) | 0.12772 (9) | 0.36528 (4) | 0.0387 (2) | |
S2 | 0.15575 (7) | −0.00994 (9) | 0.32718 (4) | 0.0382 (2) | |
P1 | 0.26239 (7) | 0.19707 (9) | 0.22109 (4) | 0.0316 (2) | |
O1 | 0.2115 (2) | −0.1033 (3) | 0.49363 (13) | 0.0791 (11) | |
O2 | 0.2652 (3) | 0.3021 (3) | 0.48103 (14) | 0.1006 (13) | |
O3 | −0.0037 (2) | 0.1481 (3) | 0.42412 (14) | 0.0962 (12) | |
O4 | 0.2502 (2) | 0.4345 (2) | 0.34576 (12) | 0.0634 (9) | |
O5 | 0.0021 (2) | 0.2479 (3) | 0.27912 (12) | 0.0661 (9) | |
N1 | 0.3407 (2) | −0.1259 (3) | 0.34951 (12) | 0.0409 (8) | |
C1 | 0.4517 (4) | −0.3802 (4) | 0.56016 (18) | 0.0874 (16) | |
H1A | 0.4496 | −0.4671 | 0.5535 | 0.131* | |
H1B | 0.4066 | −0.3592 | 0.5881 | 0.131* | |
H1C | 0.5173 | −0.3566 | 0.5741 | 0.131* | |
C2 | 0.4224 (3) | −0.3132 (4) | 0.50438 (17) | 0.0536 (11) | |
C3 | 0.3533 (3) | −0.3595 (4) | 0.46376 (18) | 0.0529 (11) | |
H3 | 0.3241 | −0.4348 | 0.4706 | 0.063* | |
C4 | 0.3255 (3) | −0.2992 (4) | 0.41345 (16) | 0.0459 (10) | |
H4 | 0.2792 | −0.3346 | 0.3870 | 0.055* | |
C5 | 0.3662 (3) | −0.1853 (4) | 0.40172 (16) | 0.0394 (9) | |
C6 | 0.4364 (3) | −0.1384 (4) | 0.44210 (17) | 0.0485 (11) | |
H6 | 0.4658 | −0.0634 | 0.4353 | 0.058* | |
C7 | 0.4635 (3) | −0.2009 (4) | 0.49226 (17) | 0.0579 (12) | |
H7 | 0.5107 | −0.1667 | 0.5186 | 0.069* | |
C8 | 0.2455 (3) | −0.1362 (3) | 0.31877 (16) | 0.0479 (11) | |
H8A | 0.2156 | −0.2121 | 0.3304 | 0.057* | |
H8B | 0.2551 | −0.1436 | 0.2783 | 0.057* | |
C9 | 0.3917 (3) | −0.0175 (3) | 0.33541 (15) | 0.0448 (10) | |
H9A | 0.3883 | −0.0103 | 0.2940 | 0.054* | |
H9B | 0.4606 | −0.0266 | 0.3490 | 0.054* | |
C10 | 0.2131 (3) | −0.0291 (4) | 0.45986 (18) | 0.0539 (12) | |
C11 | 0.2391 (3) | 0.2194 (4) | 0.45270 (18) | 0.0651 (14) | |
C12 | 0.0758 (3) | 0.1262 (4) | 0.41723 (17) | 0.0561 (12) | |
C13 | 0.2339 (3) | 0.3362 (4) | 0.32971 (15) | 0.0385 (10) | |
C14 | 0.0838 (3) | 0.2218 (3) | 0.28947 (16) | 0.0431 (10) | |
C15 | 0.0207 (4) | 0.2515 (5) | 0.0789 (2) | 0.0749 (15) | |
H15 | 0.0568 | 0.3196 | 0.0630 | 0.090* | |
C16 | −0.0165 (4) | 0.1463 (5) | 0.0488 (2) | 0.0738 (15) | |
H16 | −0.0101 | 0.1287 | 0.0081 | 0.089* | |
C17 | −0.0633 (3) | 0.0727 (5) | 0.0861 (2) | 0.0736 (15) | |
H17 | −0.0958 | −0.0058 | 0.0766 | 0.088* | |
C18 | −0.0557 (3) | 0.1293 (5) | 0.1406 (2) | 0.0686 (14) | |
H18 | −0.0826 | 0.0979 | 0.1754 | 0.082* | |
C19 | −0.0044 (3) | 0.2407 (4) | 0.1355 (2) | 0.0662 (14) | |
H19 | 0.0115 | 0.2999 | 0.1664 | 0.079* | |
C20 | 0.1400 (3) | −0.0774 (4) | 0.12177 (17) | 0.0518 (11) | |
H20 | 0.1039 | −0.1546 | 0.1152 | 0.062* | |
C21 | 0.1848 (3) | −0.0097 (4) | 0.08032 (18) | 0.0551 (12) | |
H21 | 0.1854 | −0.0312 | 0.0397 | 0.066* | |
C22 | 0.2278 (3) | 0.0960 (4) | 0.10657 (15) | 0.0440 (10) | |
H22 | 0.2638 | 0.1598 | 0.0874 | 0.053* | |
C23 | 0.2103 (2) | 0.0944 (3) | 0.16603 (14) | 0.0331 (9) | |
C24 | 0.1549 (3) | −0.0139 (3) | 0.17502 (16) | 0.0429 (10) | |
H24 | 0.1310 | −0.0401 | 0.2115 | 0.051* | |
C25 | 0.3951 (2) | 0.1685 (3) | 0.22119 (14) | 0.0303 (8) | |
C26 | 0.4591 (3) | 0.2380 (3) | 0.25719 (15) | 0.0380 (9) | |
H26 | 0.4338 | 0.2998 | 0.2791 | 0.046* | |
C27 | 0.5593 (3) | 0.2175 (4) | 0.26120 (16) | 0.0471 (11) | |
H27 | 0.6011 | 0.2650 | 0.2857 | 0.056* | |
C28 | 0.5975 (3) | 0.1257 (4) | 0.22858 (17) | 0.0483 (11) | |
H28 | 0.6650 | 0.1103 | 0.2315 | 0.058* | |
C29 | 0.5357 (3) | 0.0582 (3) | 0.19212 (16) | 0.0455 (11) | |
H29 | 0.5618 | −0.0015 | 0.1693 | 0.055* | |
C30 | 0.4351 (3) | 0.0770 (3) | 0.18864 (15) | 0.0370 (9) | |
H30 | 0.3937 | 0.0283 | 0.1645 | 0.044* | |
C31 | 0.2548 (3) | 0.3488 (3) | 0.18691 (15) | 0.0343 (9) | |
C32 | 0.3189 (3) | 0.3814 (3) | 0.14616 (16) | 0.0477 (11) | |
H32 | 0.3677 | 0.3266 | 0.1371 | 0.057* | |
C33 | 0.3115 (3) | 0.4942 (4) | 0.11883 (17) | 0.0577 (12) | |
H33 | 0.3544 | 0.5141 | 0.0913 | 0.069* | |
C34 | 0.2412 (3) | 0.5761 (4) | 0.13229 (18) | 0.0591 (12) | |
H34 | 0.2364 | 0.6519 | 0.1140 | 0.071* | |
C35 | 0.1777 (3) | 0.5472 (4) | 0.17249 (18) | 0.0547 (12) | |
H35 | 0.1301 | 0.6034 | 0.1817 | 0.066* | |
C36 | 0.1843 (3) | 0.4339 (3) | 0.19954 (15) | 0.0427 (10) | |
H36 | 0.1405 | 0.4148 | 0.2267 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0317 (3) | 0.0340 (3) | 0.0323 (3) | −0.0013 (3) | 0.0052 (2) | −0.0022 (2) |
Fe2 | 0.0415 (4) | 0.0483 (4) | 0.0305 (3) | −0.0029 (3) | 0.0065 (3) | −0.0030 (3) |
Fe3 | 0.0349 (3) | 0.0523 (4) | 0.0393 (3) | 0.0000 (3) | −0.0020 (3) | −0.0046 (3) |
S1 | 0.0357 (6) | 0.0427 (6) | 0.0374 (6) | −0.0044 (5) | 0.0019 (5) | 0.0000 (5) |
S2 | 0.0405 (6) | 0.0395 (6) | 0.0343 (6) | −0.0058 (5) | 0.0014 (5) | 0.0002 (4) |
P1 | 0.0296 (5) | 0.0336 (6) | 0.0319 (6) | 0.0006 (5) | 0.0038 (4) | −0.0019 (4) |
O1 | 0.103 (3) | 0.087 (3) | 0.051 (2) | 0.012 (2) | 0.0248 (19) | 0.0228 (18) |
O2 | 0.138 (3) | 0.099 (3) | 0.067 (3) | −0.033 (3) | 0.026 (2) | −0.042 (2) |
O3 | 0.055 (2) | 0.151 (4) | 0.084 (3) | 0.020 (2) | 0.018 (2) | −0.018 (2) |
O4 | 0.067 (2) | 0.046 (2) | 0.079 (2) | −0.0107 (16) | 0.0131 (17) | −0.0186 (16) |
O5 | 0.0356 (18) | 0.080 (2) | 0.083 (2) | 0.0090 (16) | 0.0092 (17) | 0.0150 (17) |
N1 | 0.049 (2) | 0.038 (2) | 0.036 (2) | 0.0013 (16) | 0.0032 (17) | 0.0055 (15) |
C1 | 0.098 (4) | 0.094 (4) | 0.067 (4) | −0.003 (3) | −0.013 (3) | 0.034 (3) |
C2 | 0.056 (3) | 0.057 (3) | 0.047 (3) | 0.001 (2) | 0.002 (2) | 0.018 (2) |
C3 | 0.055 (3) | 0.047 (3) | 0.058 (3) | −0.009 (2) | 0.010 (2) | 0.012 (2) |
C4 | 0.049 (3) | 0.044 (3) | 0.043 (3) | −0.006 (2) | −0.002 (2) | −0.001 (2) |
C5 | 0.041 (2) | 0.040 (3) | 0.037 (2) | 0.004 (2) | 0.0059 (19) | 0.0015 (19) |
C6 | 0.042 (3) | 0.049 (3) | 0.054 (3) | −0.007 (2) | −0.001 (2) | 0.014 (2) |
C7 | 0.050 (3) | 0.062 (3) | 0.059 (3) | −0.004 (2) | −0.011 (2) | 0.008 (2) |
C8 | 0.063 (3) | 0.035 (3) | 0.044 (3) | 0.001 (2) | −0.006 (2) | −0.0051 (19) |
C9 | 0.044 (2) | 0.046 (3) | 0.046 (3) | 0.012 (2) | 0.014 (2) | 0.009 (2) |
C10 | 0.045 (3) | 0.080 (4) | 0.039 (3) | 0.002 (2) | 0.016 (2) | −0.006 (2) |
C11 | 0.072 (3) | 0.083 (4) | 0.043 (3) | −0.010 (3) | 0.022 (3) | −0.013 (3) |
C12 | 0.056 (3) | 0.074 (3) | 0.039 (3) | 0.002 (3) | 0.005 (2) | −0.006 (2) |
C13 | 0.032 (2) | 0.044 (3) | 0.040 (2) | 0.004 (2) | 0.0056 (18) | −0.004 (2) |
C14 | 0.045 (3) | 0.037 (3) | 0.050 (3) | −0.006 (2) | 0.012 (2) | 0.0042 (19) |
C15 | 0.073 (4) | 0.067 (4) | 0.082 (4) | 0.013 (3) | −0.011 (3) | 0.016 (3) |
C16 | 0.065 (4) | 0.094 (5) | 0.058 (3) | 0.017 (3) | −0.021 (3) | −0.009 (3) |
C17 | 0.038 (3) | 0.087 (4) | 0.093 (4) | −0.001 (3) | −0.016 (3) | −0.020 (3) |
C18 | 0.035 (3) | 0.098 (4) | 0.073 (4) | 0.004 (3) | 0.005 (2) | −0.013 (3) |
C19 | 0.045 (3) | 0.071 (4) | 0.080 (4) | 0.020 (3) | −0.012 (3) | −0.021 (3) |
C20 | 0.055 (3) | 0.042 (3) | 0.056 (3) | −0.001 (2) | −0.011 (2) | −0.013 (2) |
C21 | 0.047 (3) | 0.076 (3) | 0.042 (3) | 0.003 (2) | 0.002 (2) | −0.024 (2) |
C22 | 0.038 (2) | 0.058 (3) | 0.036 (2) | −0.005 (2) | 0.0070 (19) | −0.006 (2) |
C23 | 0.030 (2) | 0.037 (2) | 0.032 (2) | 0.0003 (18) | 0.0013 (17) | −0.0005 (18) |
C24 | 0.046 (3) | 0.045 (3) | 0.036 (2) | −0.002 (2) | −0.001 (2) | −0.0014 (19) |
C25 | 0.030 (2) | 0.032 (2) | 0.030 (2) | 0.0019 (17) | 0.0070 (17) | 0.0068 (16) |
C26 | 0.037 (2) | 0.036 (2) | 0.042 (2) | −0.0003 (19) | 0.010 (2) | −0.0054 (18) |
C27 | 0.036 (2) | 0.052 (3) | 0.052 (3) | −0.010 (2) | −0.003 (2) | 0.001 (2) |
C28 | 0.025 (2) | 0.059 (3) | 0.061 (3) | 0.006 (2) | 0.004 (2) | 0.009 (2) |
C29 | 0.039 (3) | 0.046 (3) | 0.053 (3) | 0.012 (2) | 0.015 (2) | 0.000 (2) |
C30 | 0.037 (2) | 0.036 (2) | 0.038 (2) | 0.0036 (18) | 0.0033 (18) | 0.0005 (18) |
C31 | 0.032 (2) | 0.035 (2) | 0.036 (2) | 0.0001 (17) | 0.0041 (18) | 0.0048 (17) |
C32 | 0.042 (3) | 0.049 (3) | 0.053 (3) | 0.013 (2) | 0.007 (2) | 0.014 (2) |
C33 | 0.053 (3) | 0.065 (3) | 0.057 (3) | 0.006 (3) | 0.014 (2) | 0.027 (2) |
C34 | 0.060 (3) | 0.050 (3) | 0.067 (3) | 0.008 (2) | −0.001 (3) | 0.023 (2) |
C35 | 0.054 (3) | 0.045 (3) | 0.065 (3) | 0.021 (2) | 0.004 (2) | 0.009 (2) |
C36 | 0.036 (2) | 0.050 (3) | 0.043 (2) | 0.008 (2) | 0.0061 (19) | 0.001 (2) |
Fe1—C13 | 1.750 (4) | C7—H7 | 0.93 |
Fe1—C14 | 1.754 (4) | C8—H8A | 0.97 |
Fe1—P1 | 2.2565 (10) | C8—H8B | 0.97 |
Fe1—S1 | 2.2762 (11) | C9—H9A | 0.97 |
Fe1—S2 | 2.2818 (11) | C9—H9B | 0.97 |
Fe1—Fe2 | 2.5160 (8) | C15—C19 | 1.399 (5) |
Fe2—C11 | 1.761 (5) | C15—C16 | 1.417 (6) |
Fe2—C12 | 1.777 (5) | C15—H15 | 0.98 |
Fe2—C10 | 1.813 (5) | C16—C17 | 1.379 (6) |
Fe2—S2 | 2.2546 (11) | C16—H16 | 0.98 |
Fe2—S1 | 2.2867 (11) | C17—C18 | 1.413 (6) |
Fe3—C22 | 2.025 (4) | C17—H17 | 0.98 |
Fe3—C18 | 2.030 (4) | C18—C19 | 1.410 (5) |
Fe3—C16 | 2.034 (4) | C18—H18 | 0.98 |
Fe3—C17 | 2.036 (4) | C19—H19 | 0.98 |
Fe3—C24 | 2.038 (4) | C20—C21 | 1.398 (5) |
Fe3—C21 | 2.040 (4) | C20—C24 | 1.425 (5) |
Fe3—C23 | 2.041 (3) | C20—H20 | 0.98 |
Fe3—C19 | 2.043 (4) | C21—C22 | 1.409 (5) |
Fe3—C15 | 2.044 (4) | C21—H21 | 0.98 |
Fe3—C20 | 2.047 (4) | C22—C23 | 1.431 (4) |
S1—C9 | 1.864 (3) | C22—H22 | 0.98 |
S2—C8 | 1.860 (4) | C23—C24 | 1.425 (4) |
P1—C23 | 1.806 (3) | C24—H24 | 0.98 |
P1—C25 | 1.832 (3) | C25—C26 | 1.385 (4) |
P1—C31 | 1.836 (3) | C25—C30 | 1.392 (4) |
O1—C10 | 1.132 (4) | C26—C27 | 1.376 (5) |
O2—C11 | 1.157 (4) | C26—H26 | 0.93 |
O3—C12 | 1.132 (4) | C27—C28 | 1.385 (5) |
O4—C13 | 1.151 (4) | C27—H27 | 0.93 |
O5—C14 | 1.153 (4) | C28—C29 | 1.363 (5) |
N1—C5 | 1.400 (4) | C28—H28 | 0.93 |
N1—C9 | 1.421 (4) | C29—C30 | 1.380 (5) |
N1—C8 | 1.433 (4) | C29—H29 | 0.93 |
C1—C2 | 1.519 (5) | C30—H30 | 0.93 |
C1—H1A | 0.96 | C31—C36 | 1.382 (4) |
C1—H1B | 0.96 | C31—C32 | 1.391 (4) |
C1—H1C | 0.96 | C32—C33 | 1.386 (5) |
C2—C3 | 1.376 (5) | C32—H32 | 0.93 |
C2—C7 | 1.385 (5) | C33—C34 | 1.363 (5) |
C3—C4 | 1.374 (5) | C33—H33 | 0.93 |
C3—H3 | 0.93 | C34—C35 | 1.364 (5) |
C4—C5 | 1.396 (5) | C34—H34 | 0.93 |
C4—H4 | 0.93 | C35—C36 | 1.386 (4) |
C5—C6 | 1.384 (5) | C35—H35 | 0.93 |
C6—C7 | 1.381 (5) | C36—H36 | 0.93 |
C6—H6 | 0.93 | ||
C13—Fe1—C14 | 91.41 (17) | N1—C8—S2 | 117.6 (2) |
C13—Fe1—P1 | 96.67 (12) | N1—C8—H8A | 107.9 |
C14—Fe1—P1 | 97.31 (12) | S2—C8—H8A | 107.9 |
C13—Fe1—S1 | 87.66 (12) | N1—C8—H8B | 107.9 |
C14—Fe1—S1 | 159.67 (12) | S2—C8—H8B | 107.9 |
P1—Fe1—S1 | 102.97 (4) | H8A—C8—H8B | 107.2 |
C13—Fe1—S2 | 152.46 (12) | N1—C9—S1 | 115.4 (2) |
C14—Fe1—S2 | 87.77 (12) | N1—C9—H9A | 108.4 |
P1—Fe1—S2 | 110.75 (4) | S1—C9—H9A | 108.4 |
S1—Fe1—S2 | 83.80 (4) | N1—C9—H9B | 108.4 |
C13—Fe1—Fe2 | 97.87 (12) | S1—C9—H9B | 108.4 |
C14—Fe1—Fe2 | 103.39 (12) | H9A—C9—H9B | 107.5 |
P1—Fe1—Fe2 | 154.30 (4) | O1—C10—Fe2 | 173.4 (4) |
S1—Fe1—Fe2 | 56.73 (3) | O2—C11—Fe2 | 178.3 (4) |
S2—Fe1—Fe2 | 55.80 (3) | O3—C12—Fe2 | 178.3 (4) |
C11—Fe2—C12 | 90.8 (2) | O4—C13—Fe1 | 176.7 (3) |
C11—Fe2—C10 | 100.0 (2) | O5—C14—Fe1 | 176.7 (4) |
C12—Fe2—C10 | 95.26 (18) | C19—C15—C16 | 107.3 (5) |
C11—Fe2—S2 | 159.16 (15) | C19—C15—Fe3 | 69.9 (3) |
C12—Fe2—S2 | 89.71 (14) | C16—C15—Fe3 | 69.3 (3) |
C10—Fe2—S2 | 100.70 (14) | C19—C15—H15 | 126.3 |
C11—Fe2—S1 | 85.74 (13) | C16—C15—H15 | 126.4 |
C12—Fe2—S1 | 152.32 (14) | Fe3—C15—H15 | 126.4 |
C10—Fe2—S1 | 112.39 (13) | C17—C16—C15 | 108.7 (5) |
S2—Fe2—S1 | 84.18 (4) | C17—C16—Fe3 | 70.3 (3) |
C11—Fe2—Fe1 | 102.51 (14) | C15—C16—Fe3 | 70.0 (3) |
C12—Fe2—Fe1 | 97.99 (13) | C17—C16—H16 | 125.6 |
C10—Fe2—Fe1 | 153.62 (13) | C15—C16—H16 | 125.7 |
S2—Fe2—Fe1 | 56.83 (3) | Fe3—C16—H16 | 125.6 |
S1—Fe2—Fe1 | 56.34 (3) | C16—C17—C18 | 108.3 (5) |
C22—Fe3—C18 | 164.24 (18) | C16—C17—Fe3 | 70.1 (3) |
C22—Fe3—C16 | 120.53 (19) | C18—C17—Fe3 | 69.5 (2) |
C18—Fe3—C16 | 67.69 (19) | C16—C17—H17 | 126.0 |
C22—Fe3—C17 | 153.86 (18) | C18—C17—H17 | 125.7 |
C18—Fe3—C17 | 40.67 (16) | Fe3—C17—H17 | 125.8 |
C16—Fe3—C17 | 39.61 (17) | C19—C18—C17 | 107.4 (4) |
C22—Fe3—C24 | 68.59 (15) | C19—C18—Fe3 | 70.2 (2) |
C18—Fe3—C24 | 108.54 (17) | C17—C18—Fe3 | 69.9 (2) |
C16—Fe3—C24 | 159.7 (2) | C19—C18—H18 | 126.3 |
C17—Fe3—C24 | 124.54 (19) | C17—C18—H18 | 126.3 |
C22—Fe3—C21 | 40.55 (13) | Fe3—C18—H18 | 126.3 |
C18—Fe3—C21 | 154.22 (19) | C15—C19—C18 | 108.4 (4) |
C16—Fe3—C21 | 106.06 (18) | C15—C19—Fe3 | 70.0 (2) |
C17—Fe3—C21 | 118.59 (18) | C18—C19—Fe3 | 69.3 (2) |
C24—Fe3—C21 | 68.17 (16) | C15—C19—H19 | 125.9 |
C22—Fe3—C23 | 41.20 (12) | C18—C19—H19 | 125.8 |
C18—Fe3—C23 | 126.57 (17) | Fe3—C19—H19 | 126.0 |
C16—Fe3—C23 | 157.2 (2) | C21—C20—C24 | 108.1 (4) |
C17—Fe3—C23 | 162.63 (19) | C21—C20—Fe3 | 69.8 (2) |
C24—Fe3—C23 | 40.89 (12) | C24—C20—Fe3 | 69.3 (2) |
C21—Fe3—C23 | 68.77 (14) | C21—C20—H20 | 125.8 |
C22—Fe3—C19 | 127.14 (18) | C24—C20—H20 | 126.0 |
C18—Fe3—C19 | 40.50 (15) | Fe3—C20—H20 | 126.1 |
C16—Fe3—C19 | 67.59 (18) | C20—C21—C22 | 108.5 (4) |
C17—Fe3—C19 | 67.78 (18) | C20—C21—Fe3 | 70.2 (2) |
C24—Fe3—C19 | 123.45 (18) | C22—C21—Fe3 | 69.1 (2) |
C21—Fe3—C19 | 162.4 (2) | C20—C21—H21 | 125.9 |
C23—Fe3—C19 | 110.29 (16) | C22—C21—H21 | 125.6 |
C22—Fe3—C15 | 108.63 (18) | Fe3—C21—H21 | 125.7 |
C18—Fe3—C15 | 67.97 (19) | C21—C22—C23 | 108.5 (3) |
C16—Fe3—C15 | 40.67 (16) | C21—C22—Fe3 | 70.3 (2) |
C17—Fe3—C15 | 67.7 (2) | C23—C22—Fe3 | 70.00 (19) |
C24—Fe3—C15 | 158.38 (19) | C21—C22—H22 | 125.9 |
C21—Fe3—C15 | 124.6 (2) | C23—C22—H22 | 125.6 |
C23—Fe3—C15 | 122.80 (18) | Fe3—C22—H22 | 125.7 |
C19—Fe3—C15 | 40.03 (16) | C24—C23—C22 | 106.6 (3) |
C22—Fe3—C20 | 68.06 (16) | C24—C23—P1 | 126.1 (3) |
C18—Fe3—C20 | 120.63 (19) | C22—C23—P1 | 126.8 (3) |
C16—Fe3—C20 | 122.40 (18) | C24—C23—Fe3 | 69.4 (2) |
C17—Fe3—C20 | 106.01 (18) | C22—C23—Fe3 | 68.8 (2) |
C24—Fe3—C20 | 40.84 (13) | P1—C23—Fe3 | 132.96 (18) |
C21—Fe3—C20 | 40.00 (14) | C23—C24—C20 | 108.2 (3) |
C23—Fe3—C20 | 68.76 (14) | C23—C24—Fe3 | 69.7 (2) |
C19—Fe3—C20 | 157.4 (2) | C20—C24—Fe3 | 69.9 (2) |
C15—Fe3—C20 | 159.8 (2) | C23—C24—H24 | 125.9 |
C9—S1—Fe1 | 107.79 (13) | C20—C24—H24 | 125.9 |
C9—S1—Fe2 | 111.20 (12) | Fe3—C24—H24 | 125.9 |
Fe1—S1—Fe2 | 66.93 (3) | C26—C25—C30 | 118.0 (3) |
C8—S2—Fe2 | 108.94 (12) | C26—C25—P1 | 118.5 (3) |
C8—S2—Fe1 | 116.93 (13) | C30—C25—P1 | 123.4 (3) |
Fe2—S2—Fe1 | 67.37 (3) | C27—C26—C25 | 121.5 (3) |
C23—P1—C25 | 102.96 (16) | C27—C26—H26 | 119.3 |
C23—P1—C31 | 104.03 (16) | C25—C26—H26 | 119.3 |
C25—P1—C31 | 100.01 (15) | C26—C27—C28 | 119.6 (4) |
C23—P1—Fe1 | 118.32 (12) | C26—C27—H27 | 120.2 |
C25—P1—Fe1 | 112.95 (11) | C28—C27—H27 | 120.2 |
C31—P1—Fe1 | 116.22 (12) | C29—C28—C27 | 119.7 (4) |
C5—N1—C9 | 119.7 (3) | C29—C28—H28 | 120.2 |
C5—N1—C8 | 123.4 (3) | C27—C28—H28 | 120.2 |
C9—N1—C8 | 112.7 (3) | C28—C29—C30 | 120.9 (4) |
C2—C1—H1A | 109.5 | C28—C29—H29 | 119.5 |
C2—C1—H1B | 109.5 | C30—C29—H29 | 119.5 |
H1A—C1—H1B | 109.5 | C29—C30—C25 | 120.3 (4) |
C2—C1—H1C | 109.5 | C29—C30—H30 | 119.9 |
H1A—C1—H1C | 109.5 | C25—C30—H30 | 119.9 |
H1B—C1—H1C | 109.5 | C36—C31—C32 | 117.4 (3) |
C3—C2—C7 | 116.6 (4) | C36—C31—P1 | 121.7 (3) |
C3—C2—C1 | 122.2 (4) | C32—C31—P1 | 120.8 (3) |
C7—C2—C1 | 121.2 (4) | C33—C32—C31 | 121.1 (4) |
C4—C3—C2 | 122.7 (4) | C33—C32—H32 | 119.4 |
C4—C3—H3 | 118.7 | C31—C32—H32 | 119.4 |
C2—C3—H3 | 118.7 | C34—C33—C32 | 120.0 (4) |
C3—C4—C5 | 120.6 (4) | C34—C33—H33 | 120.0 |
C3—C4—H4 | 119.7 | C32—C33—H33 | 120.0 |
C5—C4—H4 | 119.7 | C33—C34—C35 | 120.3 (4) |
C6—C5—C4 | 117.1 (4) | C33—C34—H34 | 119.9 |
C6—C5—N1 | 122.2 (4) | C35—C34—H34 | 119.9 |
C4—C5—N1 | 120.6 (4) | C34—C35—C36 | 120.0 (4) |
C7—C6—C5 | 121.3 (4) | C34—C35—H35 | 120.0 |
C7—C6—H6 | 119.4 | C36—C35—H35 | 120.0 |
C5—C6—H6 | 119.4 | C31—C36—C35 | 121.3 (4) |
C6—C7—C2 | 121.7 (4) | C31—C36—H36 | 119.4 |
C6—C7—H7 | 119.1 | C35—C36—H36 | 119.4 |
C2—C7—H7 | 119.1 | ||
C13—Fe1—Fe2—C11 | −5.79 (19) | C20—Fe3—C18—C17 | −78.6 (3) |
C14—Fe1—Fe2—C11 | −99.1 (2) | C16—C15—C19—C18 | 0.7 (5) |
P1—Fe1—Fe2—C11 | 118.10 (17) | Fe3—C15—C19—C18 | −58.8 (3) |
S1—Fe1—Fe2—C11 | 76.16 (16) | C16—C15—C19—Fe3 | 59.5 (3) |
S2—Fe1—Fe2—C11 | −177.00 (16) | C17—C18—C19—C15 | −1.0 (5) |
C13—Fe1—Fe2—C12 | 86.84 (18) | Fe3—C18—C19—C15 | 59.3 (3) |
C14—Fe1—Fe2—C12 | −6.51 (19) | C17—C18—C19—Fe3 | −60.3 (3) |
P1—Fe1—Fe2—C12 | −149.28 (16) | C22—Fe3—C19—C15 | 73.8 (3) |
S1—Fe1—Fe2—C12 | 168.78 (14) | C18—Fe3—C19—C15 | −119.7 (4) |
S2—Fe1—Fe2—C12 | −84.38 (14) | C16—Fe3—C19—C15 | −38.3 (3) |
C13—Fe1—Fe2—C10 | −153.7 (3) | C17—Fe3—C19—C15 | −81.3 (3) |
C14—Fe1—Fe2—C10 | 112.9 (3) | C24—Fe3—C19—C15 | 161.0 (3) |
P1—Fe1—Fe2—C10 | −29.8 (3) | C21—Fe3—C19—C15 | 33.6 (7) |
S1—Fe1—Fe2—C10 | −71.8 (3) | C23—Fe3—C19—C15 | 117.2 (3) |
S2—Fe1—Fe2—C10 | 35.1 (3) | C20—Fe3—C19—C15 | −159.5 (4) |
C13—Fe1—Fe2—S2 | 171.21 (12) | C22—Fe3—C19—C18 | −166.5 (3) |
C14—Fe1—Fe2—S2 | 77.86 (13) | C16—Fe3—C19—C18 | 81.4 (3) |
P1—Fe1—Fe2—S2 | −64.90 (8) | C17—Fe3—C19—C18 | 38.4 (3) |
S1—Fe1—Fe2—S2 | −106.84 (4) | C24—Fe3—C19—C18 | −79.2 (3) |
C13—Fe1—Fe2—S1 | −81.95 (12) | C21—Fe3—C19—C18 | 153.3 (5) |
C14—Fe1—Fe2—S1 | −175.30 (13) | C23—Fe3—C19—C18 | −123.0 (3) |
P1—Fe1—Fe2—S1 | 41.94 (8) | C15—Fe3—C19—C18 | 119.7 (4) |
S2—Fe1—Fe2—S1 | 106.84 (4) | C20—Fe3—C19—C18 | −39.7 (6) |
C13—Fe1—S1—C9 | −152.98 (16) | C22—Fe3—C20—C21 | −37.4 (2) |
C14—Fe1—S1—C9 | 119.3 (4) | C18—Fe3—C20—C21 | 157.3 (3) |
P1—Fe1—S1—C9 | −56.67 (12) | C16—Fe3—C20—C21 | 75.7 (3) |
S2—Fe1—S1—C9 | 53.25 (12) | C17—Fe3—C20—C21 | 115.6 (3) |
Fe2—Fe1—S1—C9 | 106.02 (12) | C24—Fe3—C20—C21 | −119.6 (3) |
C13—Fe1—S1—Fe2 | 101.00 (11) | C23—Fe3—C20—C21 | −81.9 (2) |
C14—Fe1—S1—Fe2 | 13.3 (4) | C19—Fe3—C20—C21 | −173.9 (4) |
P1—Fe1—S1—Fe2 | −162.70 (4) | C15—Fe3—C20—C21 | 47.0 (6) |
S2—Fe1—S1—Fe2 | −52.78 (3) | C22—Fe3—C20—C24 | 82.2 (2) |
C11—Fe2—S1—C9 | 150.9 (2) | C18—Fe3—C20—C24 | −83.1 (3) |
C12—Fe2—S1—C9 | −125.5 (3) | C16—Fe3—C20—C24 | −164.7 (3) |
C10—Fe2—S1—C9 | 51.8 (2) | C17—Fe3—C20—C24 | −124.8 (3) |
S2—Fe2—S1—C9 | −47.37 (13) | C21—Fe3—C20—C24 | 119.6 (3) |
Fe1—Fe2—S1—C9 | −101.01 (13) | C23—Fe3—C20—C24 | 37.7 (2) |
C11—Fe2—S1—Fe1 | −108.09 (16) | C19—Fe3—C20—C24 | −54.3 (5) |
C12—Fe2—S1—Fe1 | −24.5 (3) | C15—Fe3—C20—C24 | 166.6 (5) |
C10—Fe2—S1—Fe1 | 152.84 (15) | C24—C20—C21—C22 | −0.1 (5) |
S2—Fe2—S1—Fe1 | 53.64 (3) | Fe3—C20—C21—C22 | 58.7 (3) |
C11—Fe2—S2—C8 | 120.3 (4) | C24—C20—C21—Fe3 | −58.8 (3) |
C12—Fe2—S2—C8 | −148.17 (19) | C22—Fe3—C21—C20 | 119.9 (4) |
C10—Fe2—S2—C8 | −52.87 (18) | C18—Fe3—C21—C20 | −49.8 (5) |
S1—Fe2—S2—C8 | 58.87 (13) | C16—Fe3—C21—C20 | −121.6 (3) |
Fe1—Fe2—S2—C8 | 112.07 (13) | C17—Fe3—C21—C20 | −80.8 (3) |
C11—Fe2—S2—Fe1 | 8.2 (4) | C24—Fe3—C21—C20 | 37.8 (2) |
C12—Fe2—S2—Fe1 | 99.76 (14) | C23—Fe3—C21—C20 | 81.9 (2) |
C10—Fe2—S2—Fe1 | −164.94 (13) | C19—Fe3—C21—C20 | 172.2 (5) |
S1—Fe2—S2—Fe1 | −53.20 (3) | C15—Fe3—C21—C20 | −162.2 (3) |
C13—Fe1—S2—C8 | −119.6 (3) | C18—Fe3—C21—C22 | −169.7 (4) |
C14—Fe1—S2—C8 | 151.61 (18) | C16—Fe3—C21—C22 | 118.5 (3) |
P1—Fe1—S2—C8 | 54.64 (14) | C17—Fe3—C21—C22 | 159.3 (3) |
S1—Fe1—S2—C8 | −46.91 (14) | C24—Fe3—C21—C22 | −82.1 (3) |
Fe2—Fe1—S2—C8 | −100.52 (14) | C23—Fe3—C21—C22 | −38.0 (2) |
C13—Fe1—S2—Fe2 | −19.1 (3) | C19—Fe3—C21—C22 | 52.3 (7) |
C14—Fe1—S2—Fe2 | −107.87 (12) | C15—Fe3—C21—C22 | 77.9 (3) |
P1—Fe1—S2—Fe2 | 155.17 (4) | C20—Fe3—C21—C22 | −119.9 (4) |
S1—Fe1—S2—Fe2 | 53.61 (3) | C20—C21—C22—C23 | 0.4 (5) |
C13—Fe1—P1—C23 | −153.80 (18) | Fe3—C21—C22—C23 | 59.8 (3) |
C14—Fe1—P1—C23 | −61.51 (18) | C20—C21—C22—Fe3 | −59.4 (3) |
S1—Fe1—P1—C23 | 117.07 (13) | C18—Fe3—C22—C21 | 163.4 (6) |
S2—Fe1—P1—C23 | 28.86 (14) | C16—Fe3—C22—C21 | −78.7 (3) |
Fe2—Fe1—P1—C23 | 82.08 (15) | C17—Fe3—C22—C21 | −44.7 (5) |
C13—Fe1—P1—C25 | 85.87 (17) | C24—Fe3—C22—C21 | 81.0 (3) |
C14—Fe1—P1—C25 | 178.16 (17) | C23—Fe3—C22—C21 | 119.3 (3) |
S1—Fe1—P1—C25 | −3.25 (13) | C19—Fe3—C22—C21 | −162.5 (3) |
S2—Fe1—P1—C25 | −91.46 (13) | C15—Fe3—C22—C21 | −121.8 (3) |
Fe2—Fe1—P1—C25 | −38.24 (16) | C20—Fe3—C22—C21 | 36.9 (2) |
C13—Fe1—P1—C31 | −28.89 (18) | C18—Fe3—C22—C23 | 44.1 (7) |
C14—Fe1—P1—C31 | 63.40 (18) | C16—Fe3—C22—C23 | 162.0 (2) |
S1—Fe1—P1—C31 | −118.01 (13) | C17—Fe3—C22—C23 | −164.0 (4) |
S2—Fe1—P1—C31 | 153.78 (13) | C24—Fe3—C22—C23 | −38.3 (2) |
Fe2—Fe1—P1—C31 | −153.00 (13) | C21—Fe3—C22—C23 | −119.3 (3) |
C7—C2—C3—C4 | 0.1 (6) | C19—Fe3—C22—C23 | 78.2 (3) |
C1—C2—C3—C4 | 179.4 (4) | C15—Fe3—C22—C23 | 118.9 (3) |
C2—C3—C4—C5 | −0.9 (6) | C20—Fe3—C22—C23 | −82.4 (2) |
C3—C4—C5—C6 | 1.4 (5) | C21—C22—C23—C24 | −0.6 (4) |
C3—C4—C5—N1 | 177.6 (3) | Fe3—C22—C23—C24 | 59.4 (2) |
C9—N1—C5—C6 | 3.7 (5) | C21—C22—C23—P1 | 171.5 (3) |
C8—N1—C5—C6 | −151.7 (3) | Fe3—C22—C23—P1 | −128.5 (3) |
C9—N1—C5—C4 | −172.3 (3) | C21—C22—C23—Fe3 | −60.0 (3) |
C8—N1—C5—C4 | 32.3 (5) | C25—P1—C23—C24 | 109.2 (3) |
C4—C5—C6—C7 | −1.1 (6) | C31—P1—C23—C24 | −146.8 (3) |
N1—C5—C6—C7 | −177.2 (3) | Fe1—P1—C23—C24 | −16.1 (4) |
C5—C6—C7—C2 | 0.3 (6) | C25—P1—C23—C22 | −61.3 (3) |
C3—C2—C7—C6 | 0.2 (6) | C31—P1—C23—C22 | 42.6 (4) |
C1—C2—C7—C6 | −179.0 (4) | Fe1—P1—C23—C22 | 173.3 (3) |
C5—N1—C8—S2 | 98.7 (4) | C25—P1—C23—Fe3 | −155.9 (2) |
C9—N1—C8—S2 | −58.1 (4) | C31—P1—C23—Fe3 | −51.9 (3) |
Fe2—S2—C8—N1 | −20.0 (3) | Fe1—P1—C23—Fe3 | 78.7 (3) |
Fe1—S2—C8—N1 | 53.6 (3) | C22—Fe3—C23—C24 | −118.2 (3) |
C5—N1—C9—S1 | −84.2 (4) | C18—Fe3—C23—C24 | 75.4 (3) |
C8—N1—C9—S1 | 73.6 (3) | C16—Fe3—C23—C24 | −161.7 (4) |
Fe1—S1—C9—N1 | −79.0 (3) | C17—Fe3—C23—C24 | 37.8 (6) |
Fe2—S1—C9—N1 | −7.5 (3) | C21—Fe3—C23—C24 | −80.8 (2) |
C22—Fe3—C15—C19 | −126.1 (3) | C19—Fe3—C23—C24 | 118.1 (2) |
C18—Fe3—C15—C19 | 37.5 (3) | C15—Fe3—C23—C24 | 161.0 (2) |
C16—Fe3—C15—C19 | 118.4 (4) | C20—Fe3—C23—C24 | −37.7 (2) |
C17—Fe3—C15—C19 | 81.6 (3) | C18—Fe3—C23—C22 | −166.4 (3) |
C24—Fe3—C15—C19 | −47.4 (6) | C16—Fe3—C23—C22 | −43.4 (5) |
C21—Fe3—C15—C19 | −168.2 (3) | C17—Fe3—C23—C22 | 156.0 (5) |
C23—Fe3—C15—C19 | −82.8 (3) | C24—Fe3—C23—C22 | 118.2 (3) |
C20—Fe3—C15—C19 | 157.0 (5) | C21—Fe3—C23—C22 | 37.5 (2) |
C22—Fe3—C15—C16 | 115.5 (3) | C19—Fe3—C23—C22 | −123.7 (3) |
C18—Fe3—C15—C16 | −80.9 (3) | C15—Fe3—C23—C22 | −80.8 (3) |
C17—Fe3—C15—C16 | −36.9 (3) | C20—Fe3—C23—C22 | 80.5 (2) |
C24—Fe3—C15—C16 | −165.8 (4) | C22—Fe3—C23—P1 | 121.1 (4) |
C21—Fe3—C15—C16 | 73.3 (4) | C18—Fe3—C23—P1 | −45.3 (4) |
C23—Fe3—C15—C16 | 158.8 (3) | C16—Fe3—C23—P1 | 77.7 (5) |
C19—Fe3—C15—C16 | −118.4 (4) | C17—Fe3—C23—P1 | −82.9 (6) |
C20—Fe3—C15—C16 | 38.6 (7) | C24—Fe3—C23—P1 | −120.7 (3) |
C19—C15—C16—C17 | −0.1 (5) | C21—Fe3—C23—P1 | 158.6 (3) |
Fe3—C15—C16—C17 | 59.8 (3) | C19—Fe3—C23—P1 | −2.6 (3) |
C19—C15—C16—Fe3 | −59.9 (3) | C15—Fe3—C23—P1 | 40.3 (3) |
C22—Fe3—C16—C17 | 157.2 (3) | C20—Fe3—C23—P1 | −158.4 (3) |
C18—Fe3—C16—C17 | −37.8 (3) | C22—C23—C24—C20 | 0.5 (4) |
C24—Fe3—C16—C17 | 45.4 (6) | P1—C23—C24—C20 | −171.6 (3) |
C21—Fe3—C16—C17 | 115.7 (3) | Fe3—C23—C24—C20 | 59.5 (3) |
C23—Fe3—C16—C17 | −171.0 (3) | C22—C23—C24—Fe3 | −59.0 (2) |
C19—Fe3—C16—C17 | −81.8 (3) | P1—C23—C24—Fe3 | 128.9 (3) |
C15—Fe3—C16—C17 | −119.5 (4) | C21—C20—C24—C23 | −0.2 (4) |
C20—Fe3—C16—C17 | 75.3 (4) | Fe3—C20—C24—C23 | −59.4 (3) |
C22—Fe3—C16—C15 | −83.3 (3) | C21—C20—C24—Fe3 | 59.1 (3) |
C18—Fe3—C16—C15 | 81.7 (3) | C22—Fe3—C24—C23 | 38.56 (19) |
C17—Fe3—C16—C15 | 119.5 (4) | C18—Fe3—C24—C23 | −124.9 (2) |
C24—Fe3—C16—C15 | 164.9 (4) | C16—Fe3—C24—C23 | 159.4 (5) |
C21—Fe3—C16—C15 | −124.8 (3) | C17—Fe3—C24—C23 | −167.2 (2) |
C23—Fe3—C16—C15 | −51.5 (6) | C21—Fe3—C24—C23 | 82.3 (2) |
C19—Fe3—C16—C15 | 37.7 (3) | C19—Fe3—C24—C23 | −82.6 (3) |
C20—Fe3—C16—C15 | −165.2 (3) | C15—Fe3—C24—C23 | −48.1 (5) |
C15—C16—C17—C18 | −0.6 (5) | C20—Fe3—C24—C23 | 119.3 (3) |
Fe3—C16—C17—C18 | 59.1 (3) | C22—Fe3—C24—C20 | −80.8 (2) |
C15—C16—C17—Fe3 | −59.7 (3) | C18—Fe3—C24—C20 | 115.7 (3) |
C22—Fe3—C17—C16 | −49.2 (6) | C16—Fe3—C24—C20 | 40.1 (6) |
C18—Fe3—C17—C16 | 119.5 (5) | C17—Fe3—C24—C20 | 73.5 (3) |
C24—Fe3—C17—C16 | −162.6 (3) | C21—Fe3—C24—C20 | −37.0 (2) |
C21—Fe3—C17—C16 | −80.5 (4) | C23—Fe3—C24—C20 | −119.3 (3) |
C23—Fe3—C17—C16 | 168.3 (5) | C19—Fe3—C24—C20 | 158.0 (3) |
C19—Fe3—C17—C16 | 81.2 (3) | C15—Fe3—C24—C20 | −167.4 (5) |
C15—Fe3—C17—C16 | 37.8 (3) | C23—P1—C25—C26 | 176.8 (3) |
C20—Fe3—C17—C16 | −121.8 (3) | C31—P1—C25—C26 | 69.7 (3) |
C22—Fe3—C17—C18 | −168.7 (4) | Fe1—P1—C25—C26 | −54.5 (3) |
C16—Fe3—C17—C18 | −119.5 (5) | C23—P1—C25—C30 | −6.0 (3) |
C24—Fe3—C17—C18 | 77.9 (3) | C31—P1—C25—C30 | −113.1 (3) |
C21—Fe3—C17—C18 | 160.0 (3) | Fe1—P1—C25—C30 | 122.8 (3) |
C23—Fe3—C17—C18 | 48.8 (7) | C30—C25—C26—C27 | −0.3 (5) |
C19—Fe3—C17—C18 | −38.3 (3) | P1—C25—C26—C27 | 177.1 (3) |
C15—Fe3—C17—C18 | −81.7 (3) | C25—C26—C27—C28 | 0.1 (6) |
C20—Fe3—C17—C18 | 118.6 (3) | C26—C27—C28—C29 | 1.2 (6) |
C16—C17—C18—C19 | 1.0 (5) | C27—C28—C29—C30 | −2.2 (6) |
Fe3—C17—C18—C19 | 60.5 (3) | C28—C29—C30—C25 | 2.1 (6) |
C16—C17—C18—Fe3 | −59.6 (3) | C26—C25—C30—C29 | −0.8 (5) |
C22—Fe3—C18—C19 | 43.4 (8) | P1—C25—C30—C29 | −178.0 (3) |
C16—Fe3—C18—C19 | −81.1 (3) | C23—P1—C31—C36 | 104.2 (3) |
C17—Fe3—C18—C19 | −118.0 (4) | C25—P1—C31—C36 | −149.6 (3) |
C24—Fe3—C18—C19 | 120.2 (3) | Fe1—P1—C31—C36 | −27.7 (3) |
C21—Fe3—C18—C19 | −161.8 (4) | C23—P1—C31—C32 | −74.4 (3) |
C23—Fe3—C18—C19 | 78.3 (3) | C25—P1—C31—C32 | 31.8 (3) |
C15—Fe3—C18—C19 | −37.1 (3) | Fe1—P1—C31—C32 | 153.6 (3) |
C20—Fe3—C18—C19 | 163.4 (3) | C36—C31—C32—C33 | −0.8 (6) |
C22—Fe3—C18—C17 | 161.4 (6) | P1—C31—C32—C33 | 177.8 (3) |
C16—Fe3—C18—C17 | 36.9 (3) | C31—C32—C33—C34 | 0.9 (6) |
C24—Fe3—C18—C17 | −121.8 (3) | C32—C33—C34—C35 | −0.2 (7) |
C21—Fe3—C18—C17 | −43.8 (6) | C33—C34—C35—C36 | −0.4 (7) |
C23—Fe3—C18—C17 | −163.8 (3) | C32—C31—C36—C35 | 0.2 (6) |
C19—Fe3—C18—C17 | 118.0 (4) | P1—C31—C36—C35 | −178.5 (3) |
C15—Fe3—C18—C17 | 80.9 (3) | C34—C35—C36—C31 | 0.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O2i | 0.98 | 2.53 | 3.224 (5) | 128 |
C24—H24···S2 | 0.98 | 2.72 | 3.561 (4) | 144 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe3(C5H5)(C9H11NS2)(C17H14P)(CO)5] |
Mr | 819.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.600 (2), 10.8964 (19), 23.396 (4) |
β (°) | 94.741 (3) |
V (Å3) | 3455.2 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.45 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.760, 0.868 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21457, 8202, 4258 |
Rint | 0.070 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.079, 0.80 |
No. of reflections | 8202 |
No. of parameters | 434 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.66, −0.39 |
Computer programs: SMART (Bruker, 1997), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Fe1—C13 | 1.750 (4) | Fe2—C11 | 1.761 (5) |
Fe1—P1 | 2.2565 (10) | Fe2—C12 | 1.777 (5) |
Fe1—S1 | 2.2762 (11) | Fe2—C10 | 1.813 (5) |
Fe1—S2 | 2.2818 (11) | Fe2—S2 | 2.2546 (11) |
Fe1—Fe2 | 2.5160 (8) | Fe2—S1 | 2.2867 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O2i | 0.98 | 2.53 | 3.224 (5) | 128 |
C24—H24···S2 | 0.98 | 2.72 | 3.561 (4) | 144 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
The iron-only hydrogenases are enzymes that can efficiently catalyze the reversible reaction of hydrogen production (Cammack, 1999; Evans & Pickett, 2003). The active site at which this reaction takes place is composed of a butterfly shaped Fe2S2 unit covalently linked to a conventional Fe4S4 cluster by a bridged cysteinyl thioether (Peters et al., 1998; Nicolet et al., 1999). We have prepared the title complex as a structural model for the iron-only hydrogenases active site. Herein we report its crystal structure.
The molecular structure of the title complex is shown in Fig.1 and selected bond distances are listed in Table 1. In the Fe2S2 unit, the Fe—Fe distance of 2.5160 (8) Å is slightly longer than those observed in related complexes (Lawrence et al., 2001; Ott et al., 2004). The FcPPh2 (Fc is ferrocenyl and Ph is phenyl) ligand is in apical position (trans to Fe—Fe bond), with an Fe—P distance of 2.2565 (10) Å. The Fe1—C(≡O) distances are ~0.04 Å shorter than those found in a related complex (Hou et al., 2006), consistent with an increase in the charge of Fe1 because one of the CO ligands was replaced by the FcPPh2 ligand. The ferrocene unit is covalently linked to the Fe2S2 unit via the bridged diphenyl P atom, with an Fe1—P1—C23 angle of 118.32 (12)°. The N1 atom is displaced from the C5/C8/C9 plane by 0.168 (3) Å, and the sum of angles around N1 is 355.8°.
Intramolecular C—H···S and intermolecular C—H···O hydrogen bonds are observed.