Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015246/wn6114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015246/wn6114Isup2.hkl |
CCDC reference: 197457
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.011 Å
- R factor = 0.054
- wR factor = 0.142
- Data-to-parameter ratio = 8.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5559
Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 10 for a non-centrosymmetric structure, where ZMAX > 18 sine(theta)/lambda 0.5559 Proportion of unique data used 1.0000 Ratio reflections to parameters 8.0249 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 58.99 From the CIF: _reflns_number_total 3218 From the CIF: _diffrn_reflns_limit_ max hkl 9. 16. 22. From the CIF: _diffrn_reflns_limit_ min hkl -9. -16. -23. TEST1: Expected hkl limits for theta max Calculated maximum hkl 9. 16. 26. Calculated minimum hkl -9. -16. -26. ALERT: Expected hkl max differ from CIF values REFLT_03 From the CIF: _diffrn_reflns_theta_max 58.99 From the CIF: _reflns_number_total 3218 Count of symmetry unique reflns 2497 Completeness (_total/calc) 128.87% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 721 Fraction of Friedel pairs measured 0.289 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was prepared in 38% yield from tetracarbonyl {[(8S,9R)-8-ferrocenyl-6-methyl-1,4-dithia-6-azaspiro[4,4]nonan-9- yl][(1R,3R,4S)-8-phenylmenthyloxy]methylidene}chromium(0), by oxidation promoted by exposure to sunlight (Barluenga et al., 2001). After column chromatography purification, the product was recrystallized from hexane/chloroform (20:1).
Bond distances and angles within the ferrocenyl moiety ere within normal ranges. H atoms were located in difference Fourier syntheses and refined isotropically with a common displacement parameter, some freely and the others riding on their parent atoms.
Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: DIRDIF (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[Fe(C5H5)(C29H38NO2S2)] | Dx = 1.355 Mg m−3 |
Mr = 617.66 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 1251 reflections |
a = 8.679 (8) Å | θ = 3.5–59.0° |
b = 14.784 (4) Å | µ = 5.52 mm−1 |
c = 23.593 (15) Å | T = 200 K |
V = 3027 (3) Å3 | Prism, yellow |
Z = 4 | 0.25 × 0.18 × 0.15 mm |
F(000) = 1312 |
Nonius KappaCCD diffractometer | 3218 independent reflections |
Radiation source: fine-focus sealed tube | 2699 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.031 |
Detector resolution: 9 pixels mm-1 | θmax = 59.0°, θmin = 3.5° |
ϕ scans with κ offsets | h = −9→9 |
Absorption correction: empirical (using intensity measurements) (XABS2; Parkin et al., 1995) | k = −16→16 |
Tmin = 0.238, Tmax = 0.437 | l = −23→22 |
12512 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0696P)2 + 4.833P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
3218 reflections | Δρmax = 0.36 e Å−3 |
401 parameters | Δρmin = −0.34 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1005 Friedel pairs |
Primary atom site location: Patterson | Absolute structure parameter: 0.039 (10) |
[Fe(C5H5)(C29H38NO2S2)] | V = 3027 (3) Å3 |
Mr = 617.66 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 8.679 (8) Å | µ = 5.52 mm−1 |
b = 14.784 (4) Å | T = 200 K |
c = 23.593 (15) Å | 0.25 × 0.18 × 0.15 mm |
Nonius KappaCCD diffractometer | 3218 independent reflections |
Absorption correction: empirical (using intensity measurements) (XABS2; Parkin et al., 1995) | 2699 reflections with I > 2σ(I) |
Tmin = 0.238, Tmax = 0.437 | Rint = 0.031 |
12512 measured reflections | θmax = 59.0° |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | Δρmax = 0.36 e Å−3 |
S = 1.08 | Δρmin = −0.34 e Å−3 |
3218 reflections | Absolute structure: Flack (1983), 1005 Friedel pairs |
401 parameters | Absolute structure parameter: 0.039 (10) |
0 restraints |
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 ofF2 > 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. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.83406 (14) | 0.87279 (7) | 0.94482 (5) | 0.0330 (4) | |
S1 | 1.4385 (2) | 0.66461 (16) | 0.83395 (9) | 0.0457 (6) | |
S2 | 1.2305 (2) | 0.60054 (13) | 0.74335 (8) | 0.0403 (6) | |
O1 | 1.0591 (5) | 0.5174 (3) | 0.8798 (2) | 0.0310 (12) | |
O2 | 0.9037 (6) | 0.5882 (3) | 0.8167 (2) | 0.0416 (14) | |
N1 | 1.2066 (7) | 0.7691 (4) | 0.7821 (3) | 0.0383 (17) | |
C2 | 1.0380 (9) | 0.7574 (5) | 0.8577 (3) | 0.0314 (19) | |
C15 | 0.6075 (9) | 0.3988 (5) | 0.9811 (3) | 0.043 (2) | |
H15A | 0.6595 | 0.4015 | 1.0170 | 0.046 (4)* | |
H15B | 0.5323 | 0.3511 | 0.9819 | 0.046 (4)* | |
H15C | 0.5570 | 0.4554 | 0.9739 | 0.046 (4)* | |
C18 | 1.3208 (9) | 0.3939 (5) | 0.8597 (3) | 0.0379 (19) | |
H18A | 1.2856 | 0.4523 | 0.8718 | 0.046 (4)* | |
H18B | 1.3797 | 0.4002 | 0.8255 | 0.046 (4)* | |
H18C | 1.3842 | 0.3677 | 0.8887 | 0.050 (4)* | |
C19 | 1.2316 (9) | 0.2335 (5) | 0.8534 (3) | 0.0331 (19) | |
C13 | 0.9327 (9) | 0.2746 (5) | 0.8987 (3) | 0.0329 (19) | |
H13A | 0.9874 | 0.2192 | 0.9077 | 0.046 (4)* | |
H13B | 0.8818 | 0.2661 | 0.8625 | 0.046 (4)* | |
C33 | 0.8065 (11) | 1.0000 (6) | 0.9136 (4) | 0.053 (2) | |
H33A | 0.8857 | 1.0406 | 0.9059 | 0.046 (4)* | |
C10 | 0.8359 (9) | 0.4573 (5) | 0.9270 (3) | 0.0356 (19) | |
H10A | 0.8880 | 0.4683 | 0.9627 | 0.046 (4)* | |
H10B | 0.7791 | 0.5116 | 0.9171 | 0.046 (4)* | |
C9 | 0.9566 (8) | 0.4385 (4) | 0.8810 (4) | 0.0286 (18) | |
C12 | 0.8098 (9) | 0.2923 (4) | 0.9448 (3) | 0.039 (2) | |
H12A | 0.7369 | 0.2426 | 0.9452 | 0.046 (4)* | |
H12B | 0.8594 | 0.2947 | 0.9816 | 0.046 (4)* | |
C14 | 1.0490 (8) | 0.3521 (4) | 0.8935 (3) | 0.0295 (18) | |
C22 | 1.3146 (11) | 0.0513 (5) | 0.8657 (4) | 0.053 (3) | |
H22A | 1.3409 | −0.0092 | 0.8704 | 0.046 (4)* | |
C4 | 1.2433 (9) | 0.6788 (5) | 0.8020 (3) | 0.0314 (18) | |
C26 | 0.8773 (9) | 0.7379 (5) | 0.9505 (4) | 0.042 (2) | |
C27 | 0.9935 (8) | 0.7814 (5) | 0.9172 (3) | 0.0307 (18) | |
C17 | 1.1282 (10) | 0.3500 (6) | 0.7871 (4) | 0.040 (2) | |
C32 | 0.7468 (13) | 0.9363 (7) | 0.8753 (4) | 0.060 (3) | |
C34 | 0.7287 (11) | 0.9927 (6) | 0.9642 (4) | 0.053 (3) | |
C25 | 0.8735 (10) | 0.7762 (5) | 1.0037 (4) | 0.040 (2) | |
C5 | 1.4226 (10) | 0.5536 (6) | 0.7455 (4) | 0.053 (2) | |
H5A | 1.4233 | 0.4990 | 0.7682 | 0.046 (4)* | |
H5B | 1.4560 | 0.5382 | 0.7074 | 0.046 (4)* | |
C21 | 1.1991 (10) | 0.0749 (5) | 0.8286 (4) | 0.047 (2) | |
C11 | 0.7240 (8) | 0.3801 (5) | 0.9344 (3) | 0.0365 (19) | |
H11A | 0.6668 | 0.3736 | 0.8989 | 0.046 (4)* | |
C23 | 1.3909 (11) | 0.1167 (7) | 0.8958 (4) | 0.052 (3) | |
C20 | 1.1611 (9) | 0.1655 (5) | 0.8233 (4) | 0.044 (2) | |
H20A | 1.0835 | 0.1812 | 0.7979 | 0.046 (4)* | |
C24 | 1.3498 (10) | 0.2078 (5) | 0.8907 (4) | 0.043 (2) | |
H24A | 1.4008 | 0.2514 | 0.9121 | 0.046 (4)* | |
C30 | 0.6202 (10) | 0.9222 (7) | 0.9596 (5) | 0.060 (3) | |
C8 | 1.0167 (9) | 0.5880 (5) | 0.8467 (3) | 0.0325 (19) | |
C7 | 1.3217 (10) | 0.8146 (5) | 0.7476 (4) | 0.051 (2) | |
H7A | 1.2844 | 0.8733 | 0.7369 | 0.046 (4)* | |
H7B | 1.3415 | 0.7795 | 0.7141 | 0.046 (4)* | |
H7C | 1.4153 | 0.8210 | 0.7689 | 0.046 (4)* | |
C3 | 1.1260 (8) | 0.6670 (4) | 0.8537 (3) | 0.0274 (17) | |
H3A | 1.1853 | 0.6583 | 0.8886 | 0.046 (4)* | |
C1 | 1.1505 (10) | 0.8223 (5) | 0.8292 (3) | 0.044 (2) | |
H1A | 1.0988 | 0.8766 | 0.8162 | 0.046 (4)* | |
H2B | 1.2337 | 0.8390 | 0.8546 | 0.046 (4)* | |
C31 | 0.6325 (11) | 0.8893 (6) | 0.9032 (4) | 0.057 (3) | |
H31A | 0.5728 | 0.8434 | 0.8876 | 0.046 (4)* | |
C29 | 0.9892 (9) | 0.8438 (5) | 1.0064 (3) | 0.040 (2) | |
H29A | 1.0127 | 0.8792 | 1.0378 | 0.046 (4)* | |
C6 | 1.5319 (9) | 0.6238 (6) | 0.7712 (3) | 0.047 (2) | |
H6A | 1.5497 | 0.6729 | 0.7447 | 0.046 (4)* | |
H6B | 1.6302 | 0.5962 | 0.7805 | 0.046 (4)* | |
C16 | 1.1818 (8) | 0.3326 (5) | 0.8486 (3) | 0.0311 (17) | |
C28 | 1.0623 (9) | 0.8476 (5) | 0.9529 (3) | 0.040 (2) | |
H28A | 1.1417 | 0.8867 | 0.9428 | 0.046 (4)* | |
H17B | 1.211 (8) | 0.337 (5) | 0.753 (3) | 0.046 (4)* | |
H23A | 1.459 (9) | 0.110 (6) | 0.919 (3) | 0.046 (4)* | |
H26A | 0.817 (9) | 0.691 (5) | 0.935 (3) | 0.046 (4)* | |
H30A | 0.568 (9) | 0.910 (5) | 0.995 (3) | 0.046 (4)* | |
H21A | 1.145 (8) | 0.021 (5) | 0.797 (3) | 0.046 (4)* | |
H9A | 0.908 (9) | 0.438 (5) | 0.842 (3) | 0.046 (4)* | |
H34A | 0.731 (10) | 1.014 (5) | 1.001 (3) | 0.046 (4)* | |
H17A | 1.106 (9) | 0.415 (5) | 0.783 (3) | 0.046 (4)* | |
H25A | 0.821 (8) | 0.765 (5) | 1.041 (3) | 0.046 (4)* | |
H32A | 0.790 (8) | 0.934 (5) | 0.836 (3) | 0.046 (4)* | |
H2A | 0.942 (9) | 0.751 (5) | 0.835 (3) | 0.046 (4)* | |
H14A | 1.103 (8) | 0.374 (5) | 0.930 (3) | 0.046 (4)* | |
H17C | 1.030 (9) | 0.324 (5) | 0.777 (3) | 0.046 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0350 (6) | 0.0209 (6) | 0.0433 (7) | 0.0034 (6) | 0.0018 (6) | −0.0015 (6) |
S1 | 0.0336 (11) | 0.0571 (14) | 0.0465 (13) | −0.0022 (11) | −0.0039 (10) | −0.0015 (12) |
S2 | 0.0404 (11) | 0.0385 (12) | 0.0420 (12) | −0.0032 (10) | 0.0048 (10) | −0.0089 (10) |
O1 | 0.031 (3) | 0.017 (2) | 0.045 (3) | −0.002 (2) | −0.002 (3) | −0.003 (2) |
O2 | 0.035 (3) | 0.027 (3) | 0.062 (4) | −0.006 (3) | −0.014 (3) | 0.006 (3) |
N1 | 0.046 (4) | 0.028 (3) | 0.041 (4) | 0.001 (3) | 0.016 (3) | 0.001 (3) |
C2 | 0.031 (4) | 0.016 (4) | 0.046 (5) | 0.005 (4) | 0.000 (4) | −0.003 (4) |
C15 | 0.044 (5) | 0.037 (5) | 0.048 (5) | −0.001 (4) | 0.007 (4) | −0.008 (4) |
C18 | 0.040 (4) | 0.027 (4) | 0.047 (5) | −0.001 (4) | 0.008 (4) | 0.002 (4) |
C19 | 0.032 (4) | 0.024 (4) | 0.043 (5) | −0.004 (4) | 0.009 (4) | −0.006 (4) |
C13 | 0.039 (5) | 0.015 (4) | 0.044 (5) | 0.002 (4) | −0.003 (4) | 0.013 (3) |
C33 | 0.056 (6) | 0.037 (5) | 0.067 (7) | 0.012 (5) | −0.004 (5) | 0.014 (5) |
C10 | 0.034 (4) | 0.022 (4) | 0.051 (5) | 0.003 (4) | −0.008 (4) | 0.009 (4) |
C9 | 0.031 (4) | 0.012 (4) | 0.042 (5) | −0.004 (3) | −0.004 (4) | −0.011 (4) |
C12 | 0.048 (5) | 0.024 (4) | 0.044 (5) | −0.002 (4) | 0.020 (4) | 0.008 (4) |
C14 | 0.031 (4) | 0.019 (4) | 0.038 (5) | −0.002 (3) | −0.002 (3) | −0.004 (3) |
C22 | 0.071 (7) | 0.021 (4) | 0.067 (7) | −0.006 (5) | 0.018 (6) | −0.010 (4) |
C4 | 0.035 (4) | 0.021 (4) | 0.038 (4) | −0.002 (4) | 0.000 (4) | −0.003 (4) |
C26 | 0.036 (5) | 0.028 (4) | 0.063 (6) | 0.000 (4) | 0.006 (4) | −0.001 (5) |
C27 | 0.028 (4) | 0.021 (4) | 0.043 (5) | 0.011 (4) | −0.011 (4) | −0.008 (4) |
C17 | 0.049 (5) | 0.030 (5) | 0.042 (5) | 0.005 (4) | −0.003 (4) | 0.006 (4) |
C32 | 0.069 (7) | 0.064 (7) | 0.046 (6) | 0.038 (6) | 0.026 (6) | −0.001 (6) |
C34 | 0.060 (6) | 0.037 (5) | 0.062 (7) | 0.014 (5) | 0.003 (6) | −0.023 (5) |
C25 | 0.057 (6) | 0.030 (4) | 0.032 (5) | 0.008 (4) | 0.014 (4) | −0.001 (4) |
C5 | 0.057 (6) | 0.051 (5) | 0.052 (6) | 0.012 (5) | 0.016 (5) | −0.016 (5) |
C21 | 0.054 (6) | 0.032 (5) | 0.053 (6) | −0.003 (4) | 0.003 (5) | −0.006 (4) |
C11 | 0.034 (4) | 0.032 (4) | 0.043 (5) | 0.000 (4) | −0.007 (4) | −0.003 (4) |
C23 | 0.051 (6) | 0.050 (6) | 0.054 (6) | 0.018 (5) | 0.000 (4) | 0.006 (5) |
C20 | 0.041 (4) | 0.024 (4) | 0.066 (6) | 0.003 (4) | −0.005 (5) | −0.005 (4) |
C24 | 0.044 (5) | 0.029 (4) | 0.057 (6) | 0.005 (4) | −0.005 (5) | −0.007 (4) |
C30 | 0.043 (6) | 0.063 (7) | 0.074 (8) | 0.018 (5) | 0.013 (5) | 0.017 (6) |
C8 | 0.036 (5) | 0.019 (4) | 0.042 (5) | 0.001 (4) | 0.006 (4) | −0.003 (4) |
C7 | 0.054 (5) | 0.040 (5) | 0.059 (5) | 0.002 (5) | −0.002 (5) | 0.010 (5) |
C3 | 0.035 (4) | 0.017 (3) | 0.029 (4) | −0.004 (3) | 0.005 (3) | 0.004 (3) |
C1 | 0.053 (5) | 0.031 (4) | 0.049 (5) | 0.002 (5) | 0.012 (5) | 0.004 (4) |
C31 | 0.058 (6) | 0.044 (6) | 0.069 (7) | 0.019 (5) | −0.038 (5) | −0.016 (5) |
C29 | 0.055 (5) | 0.034 (5) | 0.031 (5) | 0.011 (4) | −0.011 (4) | −0.012 (4) |
C6 | 0.040 (5) | 0.060 (5) | 0.042 (5) | 0.019 (5) | −0.004 (4) | −0.011 (5) |
C16 | 0.030 (4) | 0.021 (4) | 0.042 (5) | −0.006 (4) | 0.000 (4) | −0.005 (4) |
C28 | 0.042 (4) | 0.029 (4) | 0.050 (6) | 0.003 (4) | −0.004 (4) | −0.007 (4) |
Fe1—C31 | 2.021 (8) | C12—C11 | 1.517 (10) |
Fe1—C25 | 2.021 (8) | C12—H12A | 0.9700 |
Fe1—C28 | 2.025 (8) | C12—H12B | 0.9700 |
Fe1—C30 | 2.025 (9) | C14—C16 | 1.592 (10) |
Fe1—C29 | 2.027 (8) | C14—H14A | 1.03 (7) |
Fe1—C26 | 2.034 (8) | C22—C23 | 1.370 (13) |
Fe1—C33 | 2.034 (8) | C22—C21 | 1.376 (12) |
Fe1—C32 | 2.035 (10) | C22—H22A | 0.9300 |
Fe1—C27 | 2.041 (7) | C4—C3 | 1.598 (10) |
Fe1—C34 | 2.046 (9) | C26—C25 | 1.378 (12) |
S1—C6 | 1.793 (8) | C26—C27 | 1.431 (11) |
S1—C4 | 1.865 (8) | C26—H26A | 0.94 (7) |
S2—C5 | 1.806 (9) | C27—C28 | 1.424 (10) |
S2—C4 | 1.808 (7) | C17—C16 | 1.545 (11) |
O1—C8 | 1.354 (9) | C17—H17B | 1.09 (7) |
O1—C9 | 1.467 (8) | C17—H17A | 0.99 (8) |
O2—C8 | 1.209 (9) | C17—H17C | 0.97 (8) |
N1—C1 | 1.445 (9) | C32—C31 | 1.379 (13) |
N1—C4 | 1.451 (9) | C32—H32A | 1.01 (8) |
N1—C7 | 1.454 (10) | C34—C30 | 1.409 (13) |
C2—C27 | 1.497 (11) | C34—H34A | 0.92 (7) |
C2—C1 | 1.526 (10) | C25—C29 | 1.417 (11) |
C2—C3 | 1.543 (10) | C25—H25A | 1.00 (7) |
C2—H2A | 0.99 (8) | C5—C6 | 1.531 (11) |
C15—C11 | 1.521 (10) | C5—H5A | 0.9700 |
C15—H15A | 0.9600 | C5—H5B | 0.9700 |
C15—H15B | 0.9600 | C21—C20 | 1.386 (11) |
C15—H15C | 0.9600 | C21—H21A | 1.19 (7) |
C18—C16 | 1.532 (10) | C11—H11A | 0.9800 |
C18—H18A | 0.9600 | C23—C24 | 1.399 (11) |
C18—H18B | 0.9600 | C23—H23A | 0.81 (8) |
C18—H18C | 0.9600 | C20—H20A | 0.9300 |
C19—C20 | 1.375 (10) | C24—H24A | 0.9300 |
C19—C24 | 1.404 (11) | C30—C31 | 1.421 (13) |
C19—C16 | 1.531 (10) | C30—H30A | 0.96 (8) |
C13—C14 | 1.532 (10) | C8—C3 | 1.514 (10) |
C13—C12 | 1.545 (10) | C7—H7A | 0.9600 |
C13—H13A | 0.9700 | C7—H7B | 0.9600 |
C13—H13B | 0.9700 | C7—H7C | 0.9600 |
C33—C34 | 1.377 (12) | C3—H3A | 0.9800 |
C33—C32 | 1.403 (13) | C1—H1A | 0.9700 |
C33—H33A | 0.9300 | C1—H2B | 0.9700 |
C10—C11 | 1.508 (10) | C31—H31A | 0.9300 |
C10—C9 | 1.533 (11) | C29—C28 | 1.414 (10) |
C10—H10A | 0.9700 | C29—H29A | 0.9300 |
C10—H10B | 0.9700 | C6—H6A | 0.9700 |
C9—C14 | 1.536 (10) | C6—H6B | 0.9700 |
C9—H9A | 1.00 (8) | C28—H28A | 0.9300 |
C31—Fe1—C25 | 124.5 (4) | C25—C26—C27 | 109.4 (8) |
C31—Fe1—C28 | 156.2 (4) | C25—C26—Fe1 | 69.6 (5) |
C25—Fe1—C28 | 68.9 (3) | C27—C26—Fe1 | 69.7 (4) |
C31—Fe1—C30 | 41.1 (4) | C25—C26—H26A | 130 (5) |
C25—Fe1—C30 | 107.0 (4) | C27—C26—H26A | 120 (5) |
C28—Fe1—C30 | 161.2 (4) | Fe1—C26—H26A | 126 (5) |
C31—Fe1—C29 | 161.6 (4) | C28—C27—C26 | 106.2 (7) |
C25—Fe1—C29 | 41.0 (3) | C28—C27—C2 | 127.6 (7) |
C28—Fe1—C29 | 40.9 (3) | C26—C27—C2 | 126.2 (7) |
C30—Fe1—C29 | 124.2 (4) | C28—C27—Fe1 | 68.9 (4) |
C31—Fe1—C26 | 108.1 (4) | C26—C27—Fe1 | 69.2 (4) |
C25—Fe1—C26 | 39.7 (3) | C2—C27—Fe1 | 129.1 (5) |
C28—Fe1—C26 | 68.5 (3) | C16—C17—H17B | 117 (4) |
C30—Fe1—C26 | 120.8 (4) | C16—C17—H17A | 108 (4) |
C29—Fe1—C26 | 67.8 (3) | H17B—C17—H17A | 104 (6) |
C31—Fe1—C33 | 67.1 (4) | C16—C17—H17C | 115 (4) |
C25—Fe1—C33 | 157.3 (4) | H17B—C17—H17C | 109 (6) |
C28—Fe1—C33 | 108.6 (3) | H17A—C17—H17C | 101 (6) |
C30—Fe1—C33 | 67.7 (4) | C31—C32—C33 | 107.3 (8) |
C29—Fe1—C33 | 122.3 (4) | C31—C32—Fe1 | 69.6 (5) |
C26—Fe1—C33 | 162.2 (4) | C33—C32—Fe1 | 69.8 (5) |
C31—Fe1—C32 | 39.7 (4) | C31—C32—H32A | 134 (4) |
C25—Fe1—C32 | 160.5 (4) | C33—C32—H32A | 119 (4) |
C28—Fe1—C32 | 121.7 (4) | Fe1—C32—H32A | 126 (4) |
C30—Fe1—C32 | 68.4 (4) | C33—C34—C30 | 108.6 (9) |
C29—Fe1—C32 | 157.3 (4) | C33—C34—Fe1 | 69.8 (5) |
C26—Fe1—C32 | 125.0 (4) | C30—C34—Fe1 | 68.9 (5) |
C33—Fe1—C32 | 40.3 (4) | C33—C34—H34A | 141 (5) |
C31—Fe1—C27 | 120.8 (3) | C30—C34—H34A | 110 (5) |
C25—Fe1—C27 | 68.7 (3) | Fe1—C34—H34A | 120 (5) |
C28—Fe1—C27 | 41.0 (3) | C26—C25—C29 | 108.3 (7) |
C30—Fe1—C27 | 156.2 (4) | C26—C25—Fe1 | 70.6 (5) |
C29—Fe1—C27 | 68.8 (3) | C29—C25—Fe1 | 69.7 (4) |
C26—Fe1—C27 | 41.1 (3) | C26—C25—H25A | 138 (4) |
C33—Fe1—C27 | 125.2 (4) | C29—C25—H25A | 114 (4) |
C32—Fe1—C27 | 107.5 (3) | Fe1—C25—H25A | 130 (4) |
C31—Fe1—C34 | 67.5 (4) | C6—C5—S2 | 108.8 (5) |
C25—Fe1—C34 | 122.3 (4) | C6—C5—H5A | 109.9 |
C28—Fe1—C34 | 125.1 (4) | S2—C5—H5A | 109.9 |
C30—Fe1—C34 | 40.5 (4) | C6—C5—H5B | 109.9 |
C29—Fe1—C34 | 108.7 (4) | S2—C5—H5B | 109.9 |
C26—Fe1—C34 | 156.5 (4) | H5A—C5—H5B | 108.3 |
C33—Fe1—C34 | 39.4 (4) | C22—C21—C20 | 118.4 (8) |
C32—Fe1—C34 | 67.3 (4) | C22—C21—H21A | 121 (4) |
C27—Fe1—C34 | 161.4 (4) | C20—C21—H21A | 120 (4) |
C6—S1—C4 | 96.6 (3) | C10—C11—C12 | 110.5 (6) |
C5—S2—C4 | 99.6 (4) | C10—C11—C15 | 112.1 (6) |
C8—O1—C9 | 117.4 (6) | C12—C11—C15 | 111.4 (6) |
C1—N1—C4 | 109.0 (6) | C10—C11—H11A | 107.6 |
C1—N1—C7 | 114.2 (6) | C12—C11—H11A | 107.6 |
C4—N1—C7 | 117.2 (6) | C15—C11—H11A | 107.6 |
C27—C2—C1 | 115.5 (6) | C22—C23—C24 | 120.8 (8) |
C27—C2—C3 | 113.0 (6) | C22—C23—H23A | 128 (7) |
C1—C2—C3 | 101.6 (6) | C24—C23—H23A | 111 (7) |
C27—C2—H2A | 108 (4) | C19—C20—C21 | 123.6 (8) |
C1—C2—H2A | 111 (4) | C19—C20—H20A | 118.2 |
C3—C2—H2A | 108 (5) | C21—C20—H20A | 118.2 |
C11—C15—H15A | 109.5 | C23—C24—C19 | 120.0 (8) |
C11—C15—H15B | 109.5 | C23—C24—H24A | 120.0 |
H15A—C15—H15B | 109.5 | C19—C24—H24A | 120.0 |
C11—C15—H15C | 109.5 | C34—C30—C31 | 105.9 (9) |
H15A—C15—H15C | 109.5 | C34—C30—Fe1 | 70.6 (5) |
H15B—C15—H15C | 109.5 | C31—C30—Fe1 | 69.3 (5) |
C16—C18—H18A | 109.5 | C34—C30—H30A | 112 (5) |
C16—C18—H18B | 109.5 | C31—C30—H30A | 142 (5) |
H18A—C18—H18B | 109.5 | Fe1—C30—H30A | 121 (5) |
C16—C18—H18C | 109.5 | O2—C8—O1 | 124.1 (7) |
H18A—C18—H18C | 109.5 | O2—C8—C3 | 124.7 (7) |
H18B—C18—H18C | 109.5 | O1—C8—C3 | 111.2 (6) |
C20—C19—C24 | 116.9 (7) | N1—C7—H7A | 109.5 |
C20—C19—C16 | 122.3 (7) | N1—C7—H7B | 109.5 |
C24—C19—C16 | 120.8 (6) | H7A—C7—H7B | 109.5 |
C14—C13—C12 | 112.6 (6) | N1—C7—H7C | 109.5 |
C14—C13—H13A | 109.1 | H7A—C7—H7C | 109.5 |
C12—C13—H13A | 109.1 | H7B—C7—H7C | 109.5 |
C14—C13—H13B | 109.1 | C8—C3—C2 | 111.4 (6) |
C12—C13—H13B | 109.1 | C8—C3—C4 | 113.6 (6) |
H13A—C13—H13B | 107.8 | C2—C3—C4 | 105.5 (5) |
C34—C33—C32 | 108.9 (9) | C8—C3—H3A | 108.7 |
C34—C33—Fe1 | 70.7 (5) | C2—C3—H3A | 108.7 |
C32—C33—Fe1 | 69.9 (5) | C4—C3—H3A | 108.7 |
C34—C33—H33A | 125.5 | N1—C1—C2 | 102.3 (6) |
C32—C33—H33A | 125.5 | N1—C1—H1A | 111.3 |
Fe1—C33—H33A | 125.4 | C2—C1—H1A | 111.3 |
C11—C10—C9 | 112.7 (6) | N1—C1—H2B | 111.3 |
C11—C10—H10A | 109.1 | C2—C1—H2B | 111.3 |
C9—C10—H10A | 109.1 | H1A—C1—H2B | 109.2 |
C11—C10—H10B | 109.1 | C32—C31—C30 | 109.2 (9) |
C9—C10—H10B | 109.1 | C32—C31—Fe1 | 70.7 (6) |
H10A—C10—H10B | 107.8 | C30—C31—Fe1 | 69.6 (5) |
O1—C9—C10 | 106.6 (5) | C32—C31—H31A | 125.4 |
O1—C9—C14 | 110.4 (6) | C30—C31—H31A | 125.4 |
C10—C9—C14 | 111.8 (6) | Fe1—C31—H31A | 125.9 |
O1—C9—H9A | 104 (4) | C28—C29—C25 | 107.8 (7) |
C10—C9—H9A | 111 (4) | C28—C29—Fe1 | 69.5 (4) |
C14—C9—H9A | 113 (4) | C25—C29—Fe1 | 69.3 (5) |
C11—C12—C13 | 111.8 (6) | C28—C29—H29A | 126.1 |
C11—C12—H12A | 109.3 | C25—C29—H29A | 126.1 |
C13—C12—H12A | 109.3 | Fe1—C29—H29A | 126.7 |
C11—C12—H12B | 109.3 | C5—C6—S1 | 106.0 (6) |
C13—C12—H12B | 109.3 | C5—C6—H6A | 110.5 |
H12A—C12—H12B | 107.9 | S1—C6—H6A | 110.5 |
C13—C14—C9 | 107.1 (6) | C5—C6—H6B | 110.5 |
C13—C14—C16 | 113.2 (5) | S1—C6—H6B | 110.5 |
C9—C14—C16 | 113.7 (6) | H6A—C6—H6B | 108.7 |
C13—C14—H14A | 118 (4) | C19—C16—C18 | 109.4 (6) |
C9—C14—H14A | 98 (4) | C19—C16—C17 | 108.3 (6) |
C16—C14—H14A | 106 (4) | C18—C16—C17 | 107.4 (6) |
C23—C22—C21 | 120.3 (8) | C19—C16—C14 | 109.2 (6) |
C23—C22—H22A | 119.9 | C18—C16—C14 | 110.4 (6) |
C21—C22—H22A | 119.9 | C17—C16—C14 | 112.1 (6) |
N1—C4—C3 | 102.0 (5) | C29—C28—C27 | 108.2 (7) |
N1—C4—S2 | 109.0 (5) | C29—C28—Fe1 | 69.7 (4) |
C3—C4—S2 | 118.4 (5) | C27—C28—Fe1 | 70.1 (4) |
N1—C4—S1 | 115.7 (5) | C29—C28—H28A | 125.9 |
C3—C4—S1 | 105.0 (4) | C27—C28—H28A | 125.9 |
S2—C4—S1 | 107.1 (4) | Fe1—C28—H28A | 125.9 |
C31—Fe1—C33—C34 | 81.9 (6) | C31—Fe1—C25—C29 | −164.7 (5) |
C25—Fe1—C33—C34 | −43.5 (12) | C28—Fe1—C25—C29 | 37.7 (4) |
C28—Fe1—C33—C34 | −123.1 (6) | C30—Fe1—C25—C29 | −123.0 (5) |
C30—Fe1—C33—C34 | 37.2 (6) | C26—Fe1—C25—C29 | 119.0 (7) |
C29—Fe1—C33—C34 | −80.1 (6) | C33—Fe1—C25—C29 | −50.2 (11) |
C26—Fe1—C33—C34 | 159.5 (11) | C32—Fe1—C25—C29 | 164.1 (9) |
C32—Fe1—C33—C34 | 119.6 (8) | C27—Fe1—C25—C29 | 81.8 (5) |
C27—Fe1—C33—C34 | −165.7 (5) | C34—Fe1—C25—C29 | −81.4 (6) |
C31—Fe1—C33—C32 | −37.7 (5) | C4—S2—C5—C6 | −27.3 (7) |
C25—Fe1—C33—C32 | −163.1 (9) | C23—C22—C21—C20 | −1.0 (13) |
C28—Fe1—C33—C32 | 117.3 (6) | C9—C10—C11—C12 | 53.7 (9) |
C30—Fe1—C33—C32 | −82.4 (6) | C9—C10—C11—C15 | 178.6 (6) |
C29—Fe1—C33—C32 | 160.3 (5) | C13—C12—C11—C10 | −52.6 (9) |
C26—Fe1—C33—C32 | 39.9 (14) | C13—C12—C11—C15 | −177.9 (6) |
C27—Fe1—C33—C32 | 74.8 (6) | C21—C22—C23—C24 | 2.1 (13) |
C34—Fe1—C33—C32 | −119.6 (8) | C24—C19—C20—C21 | 1.0 (12) |
C8—O1—C9—C10 | −86.7 (7) | C16—C19—C20—C21 | −177.1 (8) |
C8—O1—C9—C14 | 151.7 (6) | C22—C21—C20—C19 | −0.5 (13) |
C11—C10—C9—O1 | −178.4 (6) | C22—C23—C24—C19 | −1.6 (13) |
C11—C10—C9—C14 | −57.7 (8) | C20—C19—C24—C23 | 0.1 (11) |
C14—C13—C12—C11 | 56.6 (8) | C16—C19—C24—C23 | 178.2 (8) |
C12—C13—C14—C9 | −57.1 (8) | C33—C34—C30—C31 | −1.9 (10) |
C12—C13—C14—C16 | 176.8 (6) | Fe1—C34—C30—C31 | −60.6 (6) |
O1—C9—C14—C13 | 175.7 (6) | C33—C34—C30—Fe1 | 58.7 (6) |
C10—C9—C14—C13 | 57.2 (8) | C31—Fe1—C30—C34 | −116.4 (8) |
O1—C9—C14—C16 | −58.5 (8) | C25—Fe1—C30—C34 | 120.2 (6) |
C10—C9—C14—C16 | −177.0 (6) | C28—Fe1—C30—C34 | 46.1 (14) |
C1—N1—C4—C3 | 29.0 (7) | C29—Fe1—C30—C34 | 78.5 (7) |
C7—N1—C4—C3 | 160.6 (6) | C26—Fe1—C30—C34 | 161.2 (6) |
C1—N1—C4—S2 | 155.0 (5) | C33—Fe1—C30—C34 | −36.3 (6) |
C7—N1—C4—S2 | −73.5 (7) | C32—Fe1—C30—C34 | −79.9 (7) |
C1—N1—C4—S1 | −84.3 (7) | C27—Fe1—C30—C34 | −164.2 (8) |
C7—N1—C4—S1 | 47.2 (8) | C25—Fe1—C30—C31 | −123.4 (6) |
C5—S2—C4—N1 | 123.2 (6) | C28—Fe1—C30—C31 | 162.5 (10) |
C5—S2—C4—C3 | −120.9 (6) | C29—Fe1—C30—C31 | −165.1 (5) |
C5—S2—C4—S1 | −2.7 (5) | C26—Fe1—C30—C31 | −82.4 (7) |
C6—S1—C4—N1 | −95.9 (6) | C33—Fe1—C30—C31 | 80.1 (6) |
C6—S1—C4—C3 | 152.6 (5) | C32—Fe1—C30—C31 | 36.5 (6) |
C6—S1—C4—S2 | 25.9 (5) | C27—Fe1—C30—C31 | −47.8 (11) |
C31—Fe1—C26—C25 | −122.6 (6) | C34—Fe1—C30—C31 | 116.4 (8) |
C28—Fe1—C26—C25 | 82.5 (5) | C9—O1—C8—O2 | −3.1 (10) |
C30—Fe1—C26—C25 | −79.3 (6) | C9—O1—C8—C3 | 175.0 (5) |
C29—Fe1—C26—C25 | 38.3 (5) | O2—C8—C3—C2 | 41.1 (10) |
C33—Fe1—C26—C25 | 166.4 (11) | O1—C8—C3—C2 | −137.0 (6) |
C32—Fe1—C26—C25 | −163.2 (6) | O2—C8—C3—C4 | −77.9 (9) |
C27—Fe1—C26—C25 | 121.0 (7) | O1—C8—C3—C4 | 104.0 (7) |
C34—Fe1—C26—C25 | −47.7 (11) | C27—C2—C3—C8 | 88.7 (8) |
C31—Fe1—C26—C27 | 116.4 (5) | C1—C2—C3—C8 | −147.0 (6) |
C25—Fe1—C26—C27 | −121.0 (7) | C27—C2—C3—C4 | −147.5 (6) |
C28—Fe1—C26—C27 | −38.6 (4) | C1—C2—C3—C4 | −23.2 (7) |
C30—Fe1—C26—C27 | 159.7 (5) | N1—C4—C3—C8 | 120.4 (6) |
C29—Fe1—C26—C27 | −82.8 (5) | S2—C4—C3—C8 | 0.8 (8) |
C33—Fe1—C26—C27 | 45.3 (14) | S1—C4—C3—C8 | −118.6 (6) |
C32—Fe1—C26—C27 | 75.8 (6) | N1—C4—C3—C2 | −2.0 (7) |
C34—Fe1—C26—C27 | −168.7 (8) | S2—C4—C3—C2 | −121.6 (6) |
C25—C26—C27—C28 | 0.8 (8) | S1—C4—C3—C2 | 119.1 (5) |
Fe1—C26—C27—C28 | 59.2 (5) | C4—N1—C1—C2 | −45.3 (8) |
C25—C26—C27—C2 | 177.7 (7) | C7—N1—C1—C2 | −178.4 (6) |
Fe1—C26—C27—C2 | −123.9 (7) | C27—C2—C1—N1 | 163.1 (6) |
C25—C26—C27—Fe1 | −58.4 (6) | C3—C2—C1—N1 | 40.5 (7) |
C1—C2—C27—C28 | −11.5 (11) | C33—C32—C31—C30 | −0.7 (10) |
C3—C2—C27—C28 | 104.8 (8) | Fe1—C32—C31—C30 | 59.1 (6) |
C1—C2—C27—C26 | 172.3 (7) | C33—C32—C31—Fe1 | −59.9 (6) |
C3—C2—C27—C26 | −71.4 (9) | C34—C30—C31—C32 | 1.6 (10) |
C1—C2—C27—Fe1 | 80.8 (9) | Fe1—C30—C31—C32 | −59.8 (6) |
C3—C2—C27—Fe1 | −162.9 (5) | C34—C30—C31—Fe1 | 61.4 (6) |
C31—Fe1—C27—C28 | 159.8 (5) | C25—Fe1—C31—C32 | −164.3 (5) |
C25—Fe1—C27—C28 | −81.9 (5) | C28—Fe1—C31—C32 | −46.0 (11) |
C30—Fe1—C27—C28 | −165.7 (9) | C30—Fe1—C31—C32 | 120.1 (8) |
C29—Fe1—C27—C28 | −37.7 (4) | C29—Fe1—C31—C32 | 162.6 (10) |
C26—Fe1—C27—C28 | −117.8 (7) | C26—Fe1—C31—C32 | −123.5 (6) |
C33—Fe1—C27—C28 | 77.6 (6) | C33—Fe1—C31—C32 | 38.2 (5) |
C32—Fe1—C27—C28 | 118.5 (5) | C27—Fe1—C31—C32 | −80.2 (6) |
C34—Fe1—C27—C28 | 48.0 (13) | C34—Fe1—C31—C32 | 81.1 (6) |
C31—Fe1—C27—C26 | −82.4 (6) | C25—Fe1—C31—C30 | 75.6 (6) |
C25—Fe1—C27—C26 | 36.0 (5) | C28—Fe1—C31—C30 | −166.2 (8) |
C28—Fe1—C27—C26 | 117.8 (7) | C29—Fe1—C31—C30 | 42.4 (13) |
C30—Fe1—C27—C26 | −47.8 (11) | C26—Fe1—C31—C30 | 116.4 (6) |
C29—Fe1—C27—C26 | 80.1 (5) | C33—Fe1—C31—C30 | −81.9 (6) |
C33—Fe1—C27—C26 | −164.6 (6) | C32—Fe1—C31—C30 | −120.1 (8) |
C32—Fe1—C27—C26 | −123.7 (6) | C27—Fe1—C31—C30 | 159.6 (5) |
C34—Fe1—C27—C26 | 165.8 (11) | C34—Fe1—C31—C30 | −39.0 (6) |
C31—Fe1—C27—C2 | 37.9 (8) | C26—C25—C29—C28 | 1.4 (9) |
C25—Fe1—C27—C2 | 156.3 (8) | Fe1—C25—C29—C28 | −59.0 (5) |
C28—Fe1—C27—C2 | −121.9 (9) | C26—C25—C29—Fe1 | 60.4 (6) |
C30—Fe1—C27—C2 | 72.5 (12) | C31—Fe1—C29—C28 | 162.8 (10) |
C29—Fe1—C27—C2 | −159.6 (8) | C25—Fe1—C29—C28 | 119.4 (6) |
C26—Fe1—C27—C2 | 120.3 (9) | C30—Fe1—C29—C28 | −164.7 (5) |
C33—Fe1—C27—C2 | −44.3 (8) | C26—Fe1—C29—C28 | 82.3 (5) |
C32—Fe1—C27—C2 | −3.4 (8) | C33—Fe1—C29—C28 | −81.2 (5) |
C34—Fe1—C27—C2 | −73.9 (14) | C32—Fe1—C29—C28 | −46.9 (10) |
C34—C33—C32—C31 | −0.5 (10) | C27—Fe1—C29—C28 | 37.9 (4) |
Fe1—C33—C32—C31 | 59.7 (6) | C34—Fe1—C29—C28 | −122.5 (5) |
C34—C33—C32—Fe1 | −60.2 (6) | C31—Fe1—C29—C25 | 43.5 (12) |
C25—Fe1—C32—C31 | 42.0 (12) | C28—Fe1—C29—C25 | −119.4 (6) |
C28—Fe1—C32—C31 | 160.1 (5) | C30—Fe1—C29—C25 | 75.9 (6) |
C30—Fe1—C32—C31 | −37.7 (5) | C26—Fe1—C29—C25 | −37.1 (4) |
C29—Fe1—C32—C31 | −165.8 (8) | C33—Fe1—C29—C25 | 159.4 (5) |
C26—Fe1—C32—C31 | 75.5 (6) | C32—Fe1—C29—C25 | −166.2 (8) |
C33—Fe1—C32—C31 | −118.3 (8) | C27—Fe1—C29—C25 | −81.5 (5) |
C27—Fe1—C32—C31 | 117.4 (5) | C34—Fe1—C29—C25 | 118.1 (5) |
C34—Fe1—C32—C31 | −81.6 (6) | S2—C5—C6—S1 | 47.7 (7) |
C31—Fe1—C32—C33 | 118.3 (8) | C4—S1—C6—C5 | −44.7 (6) |
C25—Fe1—C32—C33 | 160.3 (9) | C20—C19—C16—C18 | −150.6 (7) |
C28—Fe1—C32—C33 | −81.6 (6) | C24—C19—C16—C18 | 31.4 (9) |
C30—Fe1—C32—C33 | 80.6 (6) | C20—C19—C16—C17 | −33.9 (10) |
C29—Fe1—C32—C33 | −47.5 (11) | C24—C19—C16—C17 | 148.1 (7) |
C26—Fe1—C32—C33 | −166.1 (5) | C20—C19—C16—C14 | 88.5 (8) |
C27—Fe1—C32—C33 | −124.2 (5) | C24—C19—C16—C14 | −89.5 (8) |
C34—Fe1—C32—C33 | 36.8 (5) | C13—C14—C16—C19 | −40.0 (8) |
C32—C33—C34—C30 | 1.5 (10) | C9—C14—C16—C19 | −162.4 (6) |
Fe1—C33—C34—C30 | −58.1 (6) | C13—C14—C16—C18 | −160.2 (6) |
C32—C33—C34—Fe1 | 59.7 (6) | C9—C14—C16—C18 | 77.3 (8) |
C31—Fe1—C34—C33 | −80.8 (6) | C13—C14—C16—C17 | 80.1 (8) |
C25—Fe1—C34—C33 | 161.7 (6) | C9—C14—C16—C17 | −42.4 (8) |
C28—Fe1—C34—C33 | 76.1 (7) | C25—C29—C28—C27 | −0.9 (8) |
C30—Fe1—C34—C33 | −120.4 (9) | Fe1—C29—C28—C27 | −59.8 (5) |
C29—Fe1—C34—C33 | 118.5 (6) | C25—C29—C28—Fe1 | 58.9 (5) |
C26—Fe1—C34—C33 | −164.4 (9) | C26—C27—C28—C29 | 0.1 (8) |
C32—Fe1—C34—C33 | −37.6 (6) | C2—C27—C28—C29 | −176.7 (7) |
C27—Fe1—C34—C33 | 39.5 (14) | Fe1—C27—C28—C29 | 59.5 (5) |
C31—Fe1—C34—C30 | 39.6 (6) | C26—C27—C28—Fe1 | −59.4 (5) |
C25—Fe1—C34—C30 | −77.9 (7) | C2—C27—C28—Fe1 | 123.8 (7) |
C28—Fe1—C34—C30 | −163.5 (6) | C31—Fe1—C28—C29 | −166.6 (8) |
C29—Fe1—C34—C30 | −121.1 (6) | C25—Fe1—C28—C29 | −37.8 (4) |
C26—Fe1—C34—C30 | −44.0 (12) | C30—Fe1—C28—C29 | 42.6 (13) |
C33—Fe1—C34—C30 | 120.4 (9) | C26—Fe1—C28—C29 | −80.6 (5) |
C32—Fe1—C34—C30 | 82.8 (7) | C33—Fe1—C28—C29 | 118.2 (5) |
C27—Fe1—C34—C30 | 159.9 (10) | C32—Fe1—C28—C29 | 160.7 (5) |
C27—C26—C25—C29 | −1.3 (9) | C27—Fe1—C28—C29 | −119.2 (6) |
Fe1—C26—C25—C29 | −59.8 (5) | C34—Fe1—C28—C29 | 77.6 (6) |
C27—C26—C25—Fe1 | 58.5 (5) | C31—Fe1—C28—C27 | −47.4 (10) |
C31—Fe1—C25—C26 | 76.3 (6) | C25—Fe1—C28—C27 | 81.5 (5) |
C28—Fe1—C25—C26 | −81.3 (5) | C30—Fe1—C28—C27 | 161.9 (11) |
C30—Fe1—C25—C26 | 118.0 (6) | C29—Fe1—C28—C27 | 119.2 (6) |
C29—Fe1—C25—C26 | −119.0 (7) | C26—Fe1—C28—C27 | 38.7 (5) |
C33—Fe1—C25—C26 | −169.3 (8) | C33—Fe1—C28—C27 | −122.6 (5) |
C32—Fe1—C25—C26 | 45.1 (12) | C32—Fe1—C28—C27 | −80.1 (6) |
C27—Fe1—C25—C26 | −37.2 (5) | C34—Fe1—C28—C27 | −163.2 (5) |
C34—Fe1—C25—C26 | 159.6 (5) |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C29H38NO2S2)] |
Mr | 617.66 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 200 |
a, b, c (Å) | 8.679 (8), 14.784 (4), 23.593 (15) |
V (Å3) | 3027 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 5.52 |
Crystal size (mm) | 0.25 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (XABS2; Parkin et al., 1995) |
Tmin, Tmax | 0.238, 0.437 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12512, 3218, 2699 |
Rint | 0.031 |
θmax (°) | 59.0 |
(sin θ/λ)max (Å−1) | 0.556 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.142, 1.08 |
No. of reflections | 3218 |
No. of parameters | 401 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.36, −0.34 |
Absolute structure | Flack (1983), 1005 Friedel pairs |
Absolute structure parameter | 0.039 (10) |
Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, DIRDIF (Beurskens et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
S1—C6 | 1.793 (8) | C19—C20 | 1.375 (10) |
S1—C4 | 1.865 (8) | C19—C16 | 1.531 (10) |
S2—C5 | 1.806 (9) | C13—C14 | 1.532 (10) |
S2—C4 | 1.808 (7) | C13—C12 | 1.545 (10) |
O1—C8 | 1.354 (9) | C10—C11 | 1.508 (10) |
O1—C9 | 1.467 (8) | C10—C9 | 1.533 (11) |
N1—C1 | 1.445 (9) | C9—C14 | 1.536 (10) |
N1—C4 | 1.451 (9) | C12—C11 | 1.517 (10) |
N1—C7 | 1.454 (10) | C14—C16 | 1.592 (10) |
C2—C27 | 1.497 (11) | C4—C3 | 1.598 (10) |
C2—C1 | 1.526 (10) | C17—C16 | 1.545 (11) |
C2—C3 | 1.543 (10) | C5—C6 | 1.531 (11) |
C15—C11 | 1.521 (10) | C8—C3 | 1.514 (10) |
C18—C16 | 1.532 (10) | ||
C6—S1—C4 | 96.6 (3) | C13—C14—C16 | 113.2 (5) |
C5—S2—C4 | 99.6 (4) | C9—C14—C16 | 113.7 (6) |
C8—O1—C9 | 117.4 (6) | N1—C4—C3 | 102.0 (5) |
C1—N1—C4 | 109.0 (6) | N1—C4—S2 | 109.0 (5) |
C1—N1—C7 | 114.2 (6) | C3—C4—S2 | 118.4 (5) |
C4—N1—C7 | 117.2 (6) | N1—C4—S1 | 115.7 (5) |
C27—C2—C1 | 115.5 (6) | C3—C4—S1 | 105.0 (4) |
C27—C2—C3 | 113.0 (6) | S2—C4—S1 | 107.1 (4) |
C1—C2—C3 | 101.6 (6) | C2—C27—Fe1 | 129.1 (5) |
C20—C19—C16 | 122.3 (7) | O2—C8—O1 | 124.1 (7) |
C24—C19—C16 | 120.8 (6) | O2—C8—C3 | 124.7 (7) |
C14—C13—C12 | 112.6 (6) | O1—C8—C3 | 111.2 (6) |
C11—C10—C9 | 112.7 (6) | C8—C3—C2 | 111.4 (6) |
O1—C9—C10 | 106.6 (5) | C8—C3—C4 | 113.6 (6) |
O1—C9—C14 | 110.4 (6) | C2—C3—C4 | 105.5 (5) |
C10—C9—C14 | 111.8 (6) | N1—C1—C2 | 102.3 (6) |
C11—C12—C13 | 111.8 (6) | C5—C6—S1 | 106.0 (6) |
C13—C14—C9 | 107.1 (6) |
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This work is part of a project directed towards the study of the regio- and diastereoselective [3 + 2]-dipolar cycloaddition of chiral non-racemic Fischer carbene complexes, (1), with azomethine ylides, (2) (Barluenga et al., 2001), as shown in the reaction Scheme below. The cycloadducts formed in these reactions were new chelated tetracarbonyl chromium carbene complexes, (3), whose oxidation by exposure to sunlight yielded, among other products, the analogous esters, (4).
The absolute configuration of the title compound, (I), was unambiguously determined, the Flack (1983) parameter refining to a value of 0.039 (10). This served to determine the absolute configuration of the cycloadducts and the stereochemical course of the reaction.
Several intramolecular hydrogen-bonding contacts help to stabilize the structure. The four shortest are C9—H9A···O2 [D···A = 2.723 (9) Å and D—H···A = 104 (7)°], C2—H2A···O2 [D···A = 2.924 (9) Å and D—H···A = 107 (4)°], C18—H18A···O1 [D···A 2.952 (9) Å and D—H···A 134.8 (4)°] and C7—H7C···S1 [D···A 3.177 (9) Å and D—H···A 105.6 (5)°].