Download citation
Download citation
link to html
The absolute configuration of the title compound, [Fe(C5H5)(C29H38NO2S2)], was unambigously determined, the Flack [Acta Cryst. (1983). A39, 876-881] parameter refining to a value of 0.039 (10). Several intramolecular hydrogen-bonding contacts help to stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015246/wn6114sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015246/wn6114Isup2.hkl
Contains datablock I

CCDC reference: 197457

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](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


Amber Alert 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
Yellow Alert 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

Comment top

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)°].

Experimental top

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).

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. View of (I), with 50% probability displacement ellipsoids.
(1R,3R,4S)-8-phenylmenthyl(8S,9S)-8-ferrocenyl-6- methyl-1,4-dithia-6-azaspiro[4,4]nonan-9-carboxylate. top
Crystal data top
[Fe(C5H5)(C29H38NO2S2)]Dx = 1.355 Mg m3
Mr = 617.66Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 1251 reflections
a = 8.679 (8) Åθ = 3.5–59.0°
b = 14.784 (4) ŵ = 5.52 mm1
c = 23.593 (15) ÅT = 200 K
V = 3027 (3) Å3Prism, yellow
Z = 40.25 × 0.18 × 0.15 mm
F(000) = 1312
Data collection top
Nonius KappaCCD
diffractometer
3218 independent reflections
Radiation source: fine-focus sealed tube2699 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.031
Detector resolution: 9 pixels mm-1θmax = 59.0°, θmin = 3.5°
ϕ scans with κ offsetsh = 99
Absorption correction: empirical (using intensity measurements)
(XABS2; Parkin et al., 1995)
k = 1616
Tmin = 0.238, Tmax = 0.437l = 2322
12512 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H 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 reflectionsΔρmax = 0.36 e Å3
401 parametersΔρmin = 0.34 e Å3
0 restraintsAbsolute structure: Flack (1983), 1005 Friedel pairs
Primary atom site location: PattersonAbsolute structure parameter: 0.039 (10)
Crystal data top
[Fe(C5H5)(C29H38NO2S2)]V = 3027 (3) Å3
Mr = 617.66Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 8.679 (8) ŵ = 5.52 mm1
b = 14.784 (4) ÅT = 200 K
c = 23.593 (15) Å0.25 × 0.18 × 0.15 mm
Data collection top
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 = 0.437Rint = 0.031
12512 measured reflectionsθmax = 59.0°
Refinement top
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142Δρmax = 0.36 e Å3
S = 1.08Δρmin = 0.34 e Å3
3218 reflectionsAbsolute structure: Flack (1983), 1005 Friedel pairs
401 parametersAbsolute structure parameter: 0.039 (10)
0 restraints
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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.83406 (14)0.87279 (7)0.94482 (5)0.0330 (4)
S11.4385 (2)0.66461 (16)0.83395 (9)0.0457 (6)
S21.2305 (2)0.60054 (13)0.74335 (8)0.0403 (6)
O11.0591 (5)0.5174 (3)0.8798 (2)0.0310 (12)
O20.9037 (6)0.5882 (3)0.8167 (2)0.0416 (14)
N11.2066 (7)0.7691 (4)0.7821 (3)0.0383 (17)
C21.0380 (9)0.7574 (5)0.8577 (3)0.0314 (19)
C150.6075 (9)0.3988 (5)0.9811 (3)0.043 (2)
H15A0.65950.40151.01700.046 (4)*
H15B0.53230.35110.98190.046 (4)*
H15C0.55700.45540.97390.046 (4)*
C181.3208 (9)0.3939 (5)0.8597 (3)0.0379 (19)
H18A1.28560.45230.87180.046 (4)*
H18B1.37970.40020.82550.046 (4)*
H18C1.38420.36770.88870.050 (4)*
C191.2316 (9)0.2335 (5)0.8534 (3)0.0331 (19)
C130.9327 (9)0.2746 (5)0.8987 (3)0.0329 (19)
H13A0.98740.21920.90770.046 (4)*
H13B0.88180.26610.86250.046 (4)*
C330.8065 (11)1.0000 (6)0.9136 (4)0.053 (2)
H33A0.88571.04060.90590.046 (4)*
C100.8359 (9)0.4573 (5)0.9270 (3)0.0356 (19)
H10A0.88800.46830.96270.046 (4)*
H10B0.77910.51160.91710.046 (4)*
C90.9566 (8)0.4385 (4)0.8810 (4)0.0286 (18)
C120.8098 (9)0.2923 (4)0.9448 (3)0.039 (2)
H12A0.73690.24260.94520.046 (4)*
H12B0.85940.29470.98160.046 (4)*
C141.0490 (8)0.3521 (4)0.8935 (3)0.0295 (18)
C221.3146 (11)0.0513 (5)0.8657 (4)0.053 (3)
H22A1.34090.00920.87040.046 (4)*
C41.2433 (9)0.6788 (5)0.8020 (3)0.0314 (18)
C260.8773 (9)0.7379 (5)0.9505 (4)0.042 (2)
C270.9935 (8)0.7814 (5)0.9172 (3)0.0307 (18)
C171.1282 (10)0.3500 (6)0.7871 (4)0.040 (2)
C320.7468 (13)0.9363 (7)0.8753 (4)0.060 (3)
C340.7287 (11)0.9927 (6)0.9642 (4)0.053 (3)
C250.8735 (10)0.7762 (5)1.0037 (4)0.040 (2)
C51.4226 (10)0.5536 (6)0.7455 (4)0.053 (2)
H5A1.42330.49900.76820.046 (4)*
H5B1.45600.53820.70740.046 (4)*
C211.1991 (10)0.0749 (5)0.8286 (4)0.047 (2)
C110.7240 (8)0.3801 (5)0.9344 (3)0.0365 (19)
H11A0.66680.37360.89890.046 (4)*
C231.3909 (11)0.1167 (7)0.8958 (4)0.052 (3)
C201.1611 (9)0.1655 (5)0.8233 (4)0.044 (2)
H20A1.08350.18120.79790.046 (4)*
C241.3498 (10)0.2078 (5)0.8907 (4)0.043 (2)
H24A1.40080.25140.91210.046 (4)*
C300.6202 (10)0.9222 (7)0.9596 (5)0.060 (3)
C81.0167 (9)0.5880 (5)0.8467 (3)0.0325 (19)
C71.3217 (10)0.8146 (5)0.7476 (4)0.051 (2)
H7A1.28440.87330.73690.046 (4)*
H7B1.34150.77950.71410.046 (4)*
H7C1.41530.82100.76890.046 (4)*
C31.1260 (8)0.6670 (4)0.8537 (3)0.0274 (17)
H3A1.18530.65830.88860.046 (4)*
C11.1505 (10)0.8223 (5)0.8292 (3)0.044 (2)
H1A1.09880.87660.81620.046 (4)*
H2B1.23370.83900.85460.046 (4)*
C310.6325 (11)0.8893 (6)0.9032 (4)0.057 (3)
H31A0.57280.84340.88760.046 (4)*
C290.9892 (9)0.8438 (5)1.0064 (3)0.040 (2)
H29A1.01270.87921.03780.046 (4)*
C61.5319 (9)0.6238 (6)0.7712 (3)0.047 (2)
H6A1.54970.67290.74470.046 (4)*
H6B1.63020.59620.78050.046 (4)*
C161.1818 (8)0.3326 (5)0.8486 (3)0.0311 (17)
C281.0623 (9)0.8476 (5)0.9529 (3)0.040 (2)
H28A1.14170.88670.94280.046 (4)*
H17B1.211 (8)0.337 (5)0.753 (3)0.046 (4)*
H23A1.459 (9)0.110 (6)0.919 (3)0.046 (4)*
H26A0.817 (9)0.691 (5)0.935 (3)0.046 (4)*
H30A0.568 (9)0.910 (5)0.995 (3)0.046 (4)*
H21A1.145 (8)0.021 (5)0.797 (3)0.046 (4)*
H9A0.908 (9)0.438 (5)0.842 (3)0.046 (4)*
H34A0.731 (10)1.014 (5)1.001 (3)0.046 (4)*
H17A1.106 (9)0.415 (5)0.783 (3)0.046 (4)*
H25A0.821 (8)0.765 (5)1.041 (3)0.046 (4)*
H32A0.790 (8)0.934 (5)0.836 (3)0.046 (4)*
H2A0.942 (9)0.751 (5)0.835 (3)0.046 (4)*
H14A1.103 (8)0.374 (5)0.930 (3)0.046 (4)*
H17C1.030 (9)0.324 (5)0.777 (3)0.046 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0350 (6)0.0209 (6)0.0433 (7)0.0034 (6)0.0018 (6)0.0015 (6)
S10.0336 (11)0.0571 (14)0.0465 (13)0.0022 (11)0.0039 (10)0.0015 (12)
S20.0404 (11)0.0385 (12)0.0420 (12)0.0032 (10)0.0048 (10)0.0089 (10)
O10.031 (3)0.017 (2)0.045 (3)0.002 (2)0.002 (3)0.003 (2)
O20.035 (3)0.027 (3)0.062 (4)0.006 (3)0.014 (3)0.006 (3)
N10.046 (4)0.028 (3)0.041 (4)0.001 (3)0.016 (3)0.001 (3)
C20.031 (4)0.016 (4)0.046 (5)0.005 (4)0.000 (4)0.003 (4)
C150.044 (5)0.037 (5)0.048 (5)0.001 (4)0.007 (4)0.008 (4)
C180.040 (4)0.027 (4)0.047 (5)0.001 (4)0.008 (4)0.002 (4)
C190.032 (4)0.024 (4)0.043 (5)0.004 (4)0.009 (4)0.006 (4)
C130.039 (5)0.015 (4)0.044 (5)0.002 (4)0.003 (4)0.013 (3)
C330.056 (6)0.037 (5)0.067 (7)0.012 (5)0.004 (5)0.014 (5)
C100.034 (4)0.022 (4)0.051 (5)0.003 (4)0.008 (4)0.009 (4)
C90.031 (4)0.012 (4)0.042 (5)0.004 (3)0.004 (4)0.011 (4)
C120.048 (5)0.024 (4)0.044 (5)0.002 (4)0.020 (4)0.008 (4)
C140.031 (4)0.019 (4)0.038 (5)0.002 (3)0.002 (3)0.004 (3)
C220.071 (7)0.021 (4)0.067 (7)0.006 (5)0.018 (6)0.010 (4)
C40.035 (4)0.021 (4)0.038 (4)0.002 (4)0.000 (4)0.003 (4)
C260.036 (5)0.028 (4)0.063 (6)0.000 (4)0.006 (4)0.001 (5)
C270.028 (4)0.021 (4)0.043 (5)0.011 (4)0.011 (4)0.008 (4)
C170.049 (5)0.030 (5)0.042 (5)0.005 (4)0.003 (4)0.006 (4)
C320.069 (7)0.064 (7)0.046 (6)0.038 (6)0.026 (6)0.001 (6)
C340.060 (6)0.037 (5)0.062 (7)0.014 (5)0.003 (6)0.023 (5)
C250.057 (6)0.030 (4)0.032 (5)0.008 (4)0.014 (4)0.001 (4)
C50.057 (6)0.051 (5)0.052 (6)0.012 (5)0.016 (5)0.016 (5)
C210.054 (6)0.032 (5)0.053 (6)0.003 (4)0.003 (5)0.006 (4)
C110.034 (4)0.032 (4)0.043 (5)0.000 (4)0.007 (4)0.003 (4)
C230.051 (6)0.050 (6)0.054 (6)0.018 (5)0.000 (4)0.006 (5)
C200.041 (4)0.024 (4)0.066 (6)0.003 (4)0.005 (5)0.005 (4)
C240.044 (5)0.029 (4)0.057 (6)0.005 (4)0.005 (5)0.007 (4)
C300.043 (6)0.063 (7)0.074 (8)0.018 (5)0.013 (5)0.017 (6)
C80.036 (5)0.019 (4)0.042 (5)0.001 (4)0.006 (4)0.003 (4)
C70.054 (5)0.040 (5)0.059 (5)0.002 (5)0.002 (5)0.010 (5)
C30.035 (4)0.017 (3)0.029 (4)0.004 (3)0.005 (3)0.004 (3)
C10.053 (5)0.031 (4)0.049 (5)0.002 (5)0.012 (5)0.004 (4)
C310.058 (6)0.044 (6)0.069 (7)0.019 (5)0.038 (5)0.016 (5)
C290.055 (5)0.034 (5)0.031 (5)0.011 (4)0.011 (4)0.012 (4)
C60.040 (5)0.060 (5)0.042 (5)0.019 (5)0.004 (4)0.011 (5)
C160.030 (4)0.021 (4)0.042 (5)0.006 (4)0.000 (4)0.005 (4)
C280.042 (4)0.029 (4)0.050 (6)0.003 (4)0.004 (4)0.007 (4)
Geometric parameters (Å, º) top
Fe1—C312.021 (8)C12—C111.517 (10)
Fe1—C252.021 (8)C12—H12A0.9700
Fe1—C282.025 (8)C12—H12B0.9700
Fe1—C302.025 (9)C14—C161.592 (10)
Fe1—C292.027 (8)C14—H14A1.03 (7)
Fe1—C262.034 (8)C22—C231.370 (13)
Fe1—C332.034 (8)C22—C211.376 (12)
Fe1—C322.035 (10)C22—H22A0.9300
Fe1—C272.041 (7)C4—C31.598 (10)
Fe1—C342.046 (9)C26—C251.378 (12)
S1—C61.793 (8)C26—C271.431 (11)
S1—C41.865 (8)C26—H26A0.94 (7)
S2—C51.806 (9)C27—C281.424 (10)
S2—C41.808 (7)C17—C161.545 (11)
O1—C81.354 (9)C17—H17B1.09 (7)
O1—C91.467 (8)C17—H17A0.99 (8)
O2—C81.209 (9)C17—H17C0.97 (8)
N1—C11.445 (9)C32—C311.379 (13)
N1—C41.451 (9)C32—H32A1.01 (8)
N1—C71.454 (10)C34—C301.409 (13)
C2—C271.497 (11)C34—H34A0.92 (7)
C2—C11.526 (10)C25—C291.417 (11)
C2—C31.543 (10)C25—H25A1.00 (7)
C2—H2A0.99 (8)C5—C61.531 (11)
C15—C111.521 (10)C5—H5A0.9700
C15—H15A0.9600C5—H5B0.9700
C15—H15B0.9600C21—C201.386 (11)
C15—H15C0.9600C21—H21A1.19 (7)
C18—C161.532 (10)C11—H11A0.9800
C18—H18A0.9600C23—C241.399 (11)
C18—H18B0.9600C23—H23A0.81 (8)
C18—H18C0.9600C20—H20A0.9300
C19—C201.375 (10)C24—H24A0.9300
C19—C241.404 (11)C30—C311.421 (13)
C19—C161.531 (10)C30—H30A0.96 (8)
C13—C141.532 (10)C8—C31.514 (10)
C13—C121.545 (10)C7—H7A0.9600
C13—H13A0.9700C7—H7B0.9600
C13—H13B0.9700C7—H7C0.9600
C33—C341.377 (12)C3—H3A0.9800
C33—C321.403 (13)C1—H1A0.9700
C33—H33A0.9300C1—H2B0.9700
C10—C111.508 (10)C31—H31A0.9300
C10—C91.533 (11)C29—C281.414 (10)
C10—H10A0.9700C29—H29A0.9300
C10—H10B0.9700C6—H6A0.9700
C9—C141.536 (10)C6—H6B0.9700
C9—H9A1.00 (8)C28—H28A0.9300
C31—Fe1—C25124.5 (4)C25—C26—C27109.4 (8)
C31—Fe1—C28156.2 (4)C25—C26—Fe169.6 (5)
C25—Fe1—C2868.9 (3)C27—C26—Fe169.7 (4)
C31—Fe1—C3041.1 (4)C25—C26—H26A130 (5)
C25—Fe1—C30107.0 (4)C27—C26—H26A120 (5)
C28—Fe1—C30161.2 (4)Fe1—C26—H26A126 (5)
C31—Fe1—C29161.6 (4)C28—C27—C26106.2 (7)
C25—Fe1—C2941.0 (3)C28—C27—C2127.6 (7)
C28—Fe1—C2940.9 (3)C26—C27—C2126.2 (7)
C30—Fe1—C29124.2 (4)C28—C27—Fe168.9 (4)
C31—Fe1—C26108.1 (4)C26—C27—Fe169.2 (4)
C25—Fe1—C2639.7 (3)C2—C27—Fe1129.1 (5)
C28—Fe1—C2668.5 (3)C16—C17—H17B117 (4)
C30—Fe1—C26120.8 (4)C16—C17—H17A108 (4)
C29—Fe1—C2667.8 (3)H17B—C17—H17A104 (6)
C31—Fe1—C3367.1 (4)C16—C17—H17C115 (4)
C25—Fe1—C33157.3 (4)H17B—C17—H17C109 (6)
C28—Fe1—C33108.6 (3)H17A—C17—H17C101 (6)
C30—Fe1—C3367.7 (4)C31—C32—C33107.3 (8)
C29—Fe1—C33122.3 (4)C31—C32—Fe169.6 (5)
C26—Fe1—C33162.2 (4)C33—C32—Fe169.8 (5)
C31—Fe1—C3239.7 (4)C31—C32—H32A134 (4)
C25—Fe1—C32160.5 (4)C33—C32—H32A119 (4)
C28—Fe1—C32121.7 (4)Fe1—C32—H32A126 (4)
C30—Fe1—C3268.4 (4)C33—C34—C30108.6 (9)
C29—Fe1—C32157.3 (4)C33—C34—Fe169.8 (5)
C26—Fe1—C32125.0 (4)C30—C34—Fe168.9 (5)
C33—Fe1—C3240.3 (4)C33—C34—H34A141 (5)
C31—Fe1—C27120.8 (3)C30—C34—H34A110 (5)
C25—Fe1—C2768.7 (3)Fe1—C34—H34A120 (5)
C28—Fe1—C2741.0 (3)C26—C25—C29108.3 (7)
C30—Fe1—C27156.2 (4)C26—C25—Fe170.6 (5)
C29—Fe1—C2768.8 (3)C29—C25—Fe169.7 (4)
C26—Fe1—C2741.1 (3)C26—C25—H25A138 (4)
C33—Fe1—C27125.2 (4)C29—C25—H25A114 (4)
C32—Fe1—C27107.5 (3)Fe1—C25—H25A130 (4)
C31—Fe1—C3467.5 (4)C6—C5—S2108.8 (5)
C25—Fe1—C34122.3 (4)C6—C5—H5A109.9
C28—Fe1—C34125.1 (4)S2—C5—H5A109.9
C30—Fe1—C3440.5 (4)C6—C5—H5B109.9
C29—Fe1—C34108.7 (4)S2—C5—H5B109.9
C26—Fe1—C34156.5 (4)H5A—C5—H5B108.3
C33—Fe1—C3439.4 (4)C22—C21—C20118.4 (8)
C32—Fe1—C3467.3 (4)C22—C21—H21A121 (4)
C27—Fe1—C34161.4 (4)C20—C21—H21A120 (4)
C6—S1—C496.6 (3)C10—C11—C12110.5 (6)
C5—S2—C499.6 (4)C10—C11—C15112.1 (6)
C8—O1—C9117.4 (6)C12—C11—C15111.4 (6)
C1—N1—C4109.0 (6)C10—C11—H11A107.6
C1—N1—C7114.2 (6)C12—C11—H11A107.6
C4—N1—C7117.2 (6)C15—C11—H11A107.6
C27—C2—C1115.5 (6)C22—C23—C24120.8 (8)
C27—C2—C3113.0 (6)C22—C23—H23A128 (7)
C1—C2—C3101.6 (6)C24—C23—H23A111 (7)
C27—C2—H2A108 (4)C19—C20—C21123.6 (8)
C1—C2—H2A111 (4)C19—C20—H20A118.2
C3—C2—H2A108 (5)C21—C20—H20A118.2
C11—C15—H15A109.5C23—C24—C19120.0 (8)
C11—C15—H15B109.5C23—C24—H24A120.0
H15A—C15—H15B109.5C19—C24—H24A120.0
C11—C15—H15C109.5C34—C30—C31105.9 (9)
H15A—C15—H15C109.5C34—C30—Fe170.6 (5)
H15B—C15—H15C109.5C31—C30—Fe169.3 (5)
C16—C18—H18A109.5C34—C30—H30A112 (5)
C16—C18—H18B109.5C31—C30—H30A142 (5)
H18A—C18—H18B109.5Fe1—C30—H30A121 (5)
C16—C18—H18C109.5O2—C8—O1124.1 (7)
H18A—C18—H18C109.5O2—C8—C3124.7 (7)
H18B—C18—H18C109.5O1—C8—C3111.2 (6)
C20—C19—C24116.9 (7)N1—C7—H7A109.5
C20—C19—C16122.3 (7)N1—C7—H7B109.5
C24—C19—C16120.8 (6)H7A—C7—H7B109.5
C14—C13—C12112.6 (6)N1—C7—H7C109.5
C14—C13—H13A109.1H7A—C7—H7C109.5
C12—C13—H13A109.1H7B—C7—H7C109.5
C14—C13—H13B109.1C8—C3—C2111.4 (6)
C12—C13—H13B109.1C8—C3—C4113.6 (6)
H13A—C13—H13B107.8C2—C3—C4105.5 (5)
C34—C33—C32108.9 (9)C8—C3—H3A108.7
C34—C33—Fe170.7 (5)C2—C3—H3A108.7
C32—C33—Fe169.9 (5)C4—C3—H3A108.7
C34—C33—H33A125.5N1—C1—C2102.3 (6)
C32—C33—H33A125.5N1—C1—H1A111.3
Fe1—C33—H33A125.4C2—C1—H1A111.3
C11—C10—C9112.7 (6)N1—C1—H2B111.3
C11—C10—H10A109.1C2—C1—H2B111.3
C9—C10—H10A109.1H1A—C1—H2B109.2
C11—C10—H10B109.1C32—C31—C30109.2 (9)
C9—C10—H10B109.1C32—C31—Fe170.7 (6)
H10A—C10—H10B107.8C30—C31—Fe169.6 (5)
O1—C9—C10106.6 (5)C32—C31—H31A125.4
O1—C9—C14110.4 (6)C30—C31—H31A125.4
C10—C9—C14111.8 (6)Fe1—C31—H31A125.9
O1—C9—H9A104 (4)C28—C29—C25107.8 (7)
C10—C9—H9A111 (4)C28—C29—Fe169.5 (4)
C14—C9—H9A113 (4)C25—C29—Fe169.3 (5)
C11—C12—C13111.8 (6)C28—C29—H29A126.1
C11—C12—H12A109.3C25—C29—H29A126.1
C13—C12—H12A109.3Fe1—C29—H29A126.7
C11—C12—H12B109.3C5—C6—S1106.0 (6)
C13—C12—H12B109.3C5—C6—H6A110.5
H12A—C12—H12B107.9S1—C6—H6A110.5
C13—C14—C9107.1 (6)C5—C6—H6B110.5
C13—C14—C16113.2 (5)S1—C6—H6B110.5
C9—C14—C16113.7 (6)H6A—C6—H6B108.7
C13—C14—H14A118 (4)C19—C16—C18109.4 (6)
C9—C14—H14A98 (4)C19—C16—C17108.3 (6)
C16—C14—H14A106 (4)C18—C16—C17107.4 (6)
C23—C22—C21120.3 (8)C19—C16—C14109.2 (6)
C23—C22—H22A119.9C18—C16—C14110.4 (6)
C21—C22—H22A119.9C17—C16—C14112.1 (6)
N1—C4—C3102.0 (5)C29—C28—C27108.2 (7)
N1—C4—S2109.0 (5)C29—C28—Fe169.7 (4)
C3—C4—S2118.4 (5)C27—C28—Fe170.1 (4)
N1—C4—S1115.7 (5)C29—C28—H28A125.9
C3—C4—S1105.0 (4)C27—C28—H28A125.9
S2—C4—S1107.1 (4)Fe1—C28—H28A125.9
C31—Fe1—C33—C3481.9 (6)C31—Fe1—C25—C29164.7 (5)
C25—Fe1—C33—C3443.5 (12)C28—Fe1—C25—C2937.7 (4)
C28—Fe1—C33—C34123.1 (6)C30—Fe1—C25—C29123.0 (5)
C30—Fe1—C33—C3437.2 (6)C26—Fe1—C25—C29119.0 (7)
C29—Fe1—C33—C3480.1 (6)C33—Fe1—C25—C2950.2 (11)
C26—Fe1—C33—C34159.5 (11)C32—Fe1—C25—C29164.1 (9)
C32—Fe1—C33—C34119.6 (8)C27—Fe1—C25—C2981.8 (5)
C27—Fe1—C33—C34165.7 (5)C34—Fe1—C25—C2981.4 (6)
C31—Fe1—C33—C3237.7 (5)C4—S2—C5—C627.3 (7)
C25—Fe1—C33—C32163.1 (9)C23—C22—C21—C201.0 (13)
C28—Fe1—C33—C32117.3 (6)C9—C10—C11—C1253.7 (9)
C30—Fe1—C33—C3282.4 (6)C9—C10—C11—C15178.6 (6)
C29—Fe1—C33—C32160.3 (5)C13—C12—C11—C1052.6 (9)
C26—Fe1—C33—C3239.9 (14)C13—C12—C11—C15177.9 (6)
C27—Fe1—C33—C3274.8 (6)C21—C22—C23—C242.1 (13)
C34—Fe1—C33—C32119.6 (8)C24—C19—C20—C211.0 (12)
C8—O1—C9—C1086.7 (7)C16—C19—C20—C21177.1 (8)
C8—O1—C9—C14151.7 (6)C22—C21—C20—C190.5 (13)
C11—C10—C9—O1178.4 (6)C22—C23—C24—C191.6 (13)
C11—C10—C9—C1457.7 (8)C20—C19—C24—C230.1 (11)
C14—C13—C12—C1156.6 (8)C16—C19—C24—C23178.2 (8)
C12—C13—C14—C957.1 (8)C33—C34—C30—C311.9 (10)
C12—C13—C14—C16176.8 (6)Fe1—C34—C30—C3160.6 (6)
O1—C9—C14—C13175.7 (6)C33—C34—C30—Fe158.7 (6)
C10—C9—C14—C1357.2 (8)C31—Fe1—C30—C34116.4 (8)
O1—C9—C14—C1658.5 (8)C25—Fe1—C30—C34120.2 (6)
C10—C9—C14—C16177.0 (6)C28—Fe1—C30—C3446.1 (14)
C1—N1—C4—C329.0 (7)C29—Fe1—C30—C3478.5 (7)
C7—N1—C4—C3160.6 (6)C26—Fe1—C30—C34161.2 (6)
C1—N1—C4—S2155.0 (5)C33—Fe1—C30—C3436.3 (6)
C7—N1—C4—S273.5 (7)C32—Fe1—C30—C3479.9 (7)
C1—N1—C4—S184.3 (7)C27—Fe1—C30—C34164.2 (8)
C7—N1—C4—S147.2 (8)C25—Fe1—C30—C31123.4 (6)
C5—S2—C4—N1123.2 (6)C28—Fe1—C30—C31162.5 (10)
C5—S2—C4—C3120.9 (6)C29—Fe1—C30—C31165.1 (5)
C5—S2—C4—S12.7 (5)C26—Fe1—C30—C3182.4 (7)
C6—S1—C4—N195.9 (6)C33—Fe1—C30—C3180.1 (6)
C6—S1—C4—C3152.6 (5)C32—Fe1—C30—C3136.5 (6)
C6—S1—C4—S225.9 (5)C27—Fe1—C30—C3147.8 (11)
C31—Fe1—C26—C25122.6 (6)C34—Fe1—C30—C31116.4 (8)
C28—Fe1—C26—C2582.5 (5)C9—O1—C8—O23.1 (10)
C30—Fe1—C26—C2579.3 (6)C9—O1—C8—C3175.0 (5)
C29—Fe1—C26—C2538.3 (5)O2—C8—C3—C241.1 (10)
C33—Fe1—C26—C25166.4 (11)O1—C8—C3—C2137.0 (6)
C32—Fe1—C26—C25163.2 (6)O2—C8—C3—C477.9 (9)
C27—Fe1—C26—C25121.0 (7)O1—C8—C3—C4104.0 (7)
C34—Fe1—C26—C2547.7 (11)C27—C2—C3—C888.7 (8)
C31—Fe1—C26—C27116.4 (5)C1—C2—C3—C8147.0 (6)
C25—Fe1—C26—C27121.0 (7)C27—C2—C3—C4147.5 (6)
C28—Fe1—C26—C2738.6 (4)C1—C2—C3—C423.2 (7)
C30—Fe1—C26—C27159.7 (5)N1—C4—C3—C8120.4 (6)
C29—Fe1—C26—C2782.8 (5)S2—C4—C3—C80.8 (8)
C33—Fe1—C26—C2745.3 (14)S1—C4—C3—C8118.6 (6)
C32—Fe1—C26—C2775.8 (6)N1—C4—C3—C22.0 (7)
C34—Fe1—C26—C27168.7 (8)S2—C4—C3—C2121.6 (6)
C25—C26—C27—C280.8 (8)S1—C4—C3—C2119.1 (5)
Fe1—C26—C27—C2859.2 (5)C4—N1—C1—C245.3 (8)
C25—C26—C27—C2177.7 (7)C7—N1—C1—C2178.4 (6)
Fe1—C26—C27—C2123.9 (7)C27—C2—C1—N1163.1 (6)
C25—C26—C27—Fe158.4 (6)C3—C2—C1—N140.5 (7)
C1—C2—C27—C2811.5 (11)C33—C32—C31—C300.7 (10)
C3—C2—C27—C28104.8 (8)Fe1—C32—C31—C3059.1 (6)
C1—C2—C27—C26172.3 (7)C33—C32—C31—Fe159.9 (6)
C3—C2—C27—C2671.4 (9)C34—C30—C31—C321.6 (10)
C1—C2—C27—Fe180.8 (9)Fe1—C30—C31—C3259.8 (6)
C3—C2—C27—Fe1162.9 (5)C34—C30—C31—Fe161.4 (6)
C31—Fe1—C27—C28159.8 (5)C25—Fe1—C31—C32164.3 (5)
C25—Fe1—C27—C2881.9 (5)C28—Fe1—C31—C3246.0 (11)
C30—Fe1—C27—C28165.7 (9)C30—Fe1—C31—C32120.1 (8)
C29—Fe1—C27—C2837.7 (4)C29—Fe1—C31—C32162.6 (10)
C26—Fe1—C27—C28117.8 (7)C26—Fe1—C31—C32123.5 (6)
C33—Fe1—C27—C2877.6 (6)C33—Fe1—C31—C3238.2 (5)
C32—Fe1—C27—C28118.5 (5)C27—Fe1—C31—C3280.2 (6)
C34—Fe1—C27—C2848.0 (13)C34—Fe1—C31—C3281.1 (6)
C31—Fe1—C27—C2682.4 (6)C25—Fe1—C31—C3075.6 (6)
C25—Fe1—C27—C2636.0 (5)C28—Fe1—C31—C30166.2 (8)
C28—Fe1—C27—C26117.8 (7)C29—Fe1—C31—C3042.4 (13)
C30—Fe1—C27—C2647.8 (11)C26—Fe1—C31—C30116.4 (6)
C29—Fe1—C27—C2680.1 (5)C33—Fe1—C31—C3081.9 (6)
C33—Fe1—C27—C26164.6 (6)C32—Fe1—C31—C30120.1 (8)
C32—Fe1—C27—C26123.7 (6)C27—Fe1—C31—C30159.6 (5)
C34—Fe1—C27—C26165.8 (11)C34—Fe1—C31—C3039.0 (6)
C31—Fe1—C27—C237.9 (8)C26—C25—C29—C281.4 (9)
C25—Fe1—C27—C2156.3 (8)Fe1—C25—C29—C2859.0 (5)
C28—Fe1—C27—C2121.9 (9)C26—C25—C29—Fe160.4 (6)
C30—Fe1—C27—C272.5 (12)C31—Fe1—C29—C28162.8 (10)
C29—Fe1—C27—C2159.6 (8)C25—Fe1—C29—C28119.4 (6)
C26—Fe1—C27—C2120.3 (9)C30—Fe1—C29—C28164.7 (5)
C33—Fe1—C27—C244.3 (8)C26—Fe1—C29—C2882.3 (5)
C32—Fe1—C27—C23.4 (8)C33—Fe1—C29—C2881.2 (5)
C34—Fe1—C27—C273.9 (14)C32—Fe1—C29—C2846.9 (10)
C34—C33—C32—C310.5 (10)C27—Fe1—C29—C2837.9 (4)
Fe1—C33—C32—C3159.7 (6)C34—Fe1—C29—C28122.5 (5)
C34—C33—C32—Fe160.2 (6)C31—Fe1—C29—C2543.5 (12)
C25—Fe1—C32—C3142.0 (12)C28—Fe1—C29—C25119.4 (6)
C28—Fe1—C32—C31160.1 (5)C30—Fe1—C29—C2575.9 (6)
C30—Fe1—C32—C3137.7 (5)C26—Fe1—C29—C2537.1 (4)
C29—Fe1—C32—C31165.8 (8)C33—Fe1—C29—C25159.4 (5)
C26—Fe1—C32—C3175.5 (6)C32—Fe1—C29—C25166.2 (8)
C33—Fe1—C32—C31118.3 (8)C27—Fe1—C29—C2581.5 (5)
C27—Fe1—C32—C31117.4 (5)C34—Fe1—C29—C25118.1 (5)
C34—Fe1—C32—C3181.6 (6)S2—C5—C6—S147.7 (7)
C31—Fe1—C32—C33118.3 (8)C4—S1—C6—C544.7 (6)
C25—Fe1—C32—C33160.3 (9)C20—C19—C16—C18150.6 (7)
C28—Fe1—C32—C3381.6 (6)C24—C19—C16—C1831.4 (9)
C30—Fe1—C32—C3380.6 (6)C20—C19—C16—C1733.9 (10)
C29—Fe1—C32—C3347.5 (11)C24—C19—C16—C17148.1 (7)
C26—Fe1—C32—C33166.1 (5)C20—C19—C16—C1488.5 (8)
C27—Fe1—C32—C33124.2 (5)C24—C19—C16—C1489.5 (8)
C34—Fe1—C32—C3336.8 (5)C13—C14—C16—C1940.0 (8)
C32—C33—C34—C301.5 (10)C9—C14—C16—C19162.4 (6)
Fe1—C33—C34—C3058.1 (6)C13—C14—C16—C18160.2 (6)
C32—C33—C34—Fe159.7 (6)C9—C14—C16—C1877.3 (8)
C31—Fe1—C34—C3380.8 (6)C13—C14—C16—C1780.1 (8)
C25—Fe1—C34—C33161.7 (6)C9—C14—C16—C1742.4 (8)
C28—Fe1—C34—C3376.1 (7)C25—C29—C28—C270.9 (8)
C30—Fe1—C34—C33120.4 (9)Fe1—C29—C28—C2759.8 (5)
C29—Fe1—C34—C33118.5 (6)C25—C29—C28—Fe158.9 (5)
C26—Fe1—C34—C33164.4 (9)C26—C27—C28—C290.1 (8)
C32—Fe1—C34—C3337.6 (6)C2—C27—C28—C29176.7 (7)
C27—Fe1—C34—C3339.5 (14)Fe1—C27—C28—C2959.5 (5)
C31—Fe1—C34—C3039.6 (6)C26—C27—C28—Fe159.4 (5)
C25—Fe1—C34—C3077.9 (7)C2—C27—C28—Fe1123.8 (7)
C28—Fe1—C34—C30163.5 (6)C31—Fe1—C28—C29166.6 (8)
C29—Fe1—C34—C30121.1 (6)C25—Fe1—C28—C2937.8 (4)
C26—Fe1—C34—C3044.0 (12)C30—Fe1—C28—C2942.6 (13)
C33—Fe1—C34—C30120.4 (9)C26—Fe1—C28—C2980.6 (5)
C32—Fe1—C34—C3082.8 (7)C33—Fe1—C28—C29118.2 (5)
C27—Fe1—C34—C30159.9 (10)C32—Fe1—C28—C29160.7 (5)
C27—C26—C25—C291.3 (9)C27—Fe1—C28—C29119.2 (6)
Fe1—C26—C25—C2959.8 (5)C34—Fe1—C28—C2977.6 (6)
C27—C26—C25—Fe158.5 (5)C31—Fe1—C28—C2747.4 (10)
C31—Fe1—C25—C2676.3 (6)C25—Fe1—C28—C2781.5 (5)
C28—Fe1—C25—C2681.3 (5)C30—Fe1—C28—C27161.9 (11)
C30—Fe1—C25—C26118.0 (6)C29—Fe1—C28—C27119.2 (6)
C29—Fe1—C25—C26119.0 (7)C26—Fe1—C28—C2738.7 (5)
C33—Fe1—C25—C26169.3 (8)C33—Fe1—C28—C27122.6 (5)
C32—Fe1—C25—C2645.1 (12)C32—Fe1—C28—C2780.1 (6)
C27—Fe1—C25—C2637.2 (5)C34—Fe1—C28—C27163.2 (5)
C34—Fe1—C25—C26159.6 (5)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C29H38NO2S2)]
Mr617.66
Crystal system, space groupOrthorhombic, P212121
Temperature (K)200
a, b, c (Å)8.679 (8), 14.784 (4), 23.593 (15)
V3)3027 (3)
Z4
Radiation typeCu Kα
µ (mm1)5.52
Crystal size (mm)0.25 × 0.18 × 0.15
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(XABS2; Parkin et al., 1995)
Tmin, Tmax0.238, 0.437
No. of measured, independent and
observed [I > 2σ(I)] reflections
12512, 3218, 2699
Rint0.031
θmax (°)59.0
(sin θ/λ)max1)0.556
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.142, 1.08
No. of reflections3218
No. of parameters401
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.36, 0.34
Absolute structureFlack (1983), 1005 Friedel pairs
Absolute structure parameter0.039 (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.

Selected geometric parameters (Å, º) top
S1—C61.793 (8)C19—C201.375 (10)
S1—C41.865 (8)C19—C161.531 (10)
S2—C51.806 (9)C13—C141.532 (10)
S2—C41.808 (7)C13—C121.545 (10)
O1—C81.354 (9)C10—C111.508 (10)
O1—C91.467 (8)C10—C91.533 (11)
N1—C11.445 (9)C9—C141.536 (10)
N1—C41.451 (9)C12—C111.517 (10)
N1—C71.454 (10)C14—C161.592 (10)
C2—C271.497 (11)C4—C31.598 (10)
C2—C11.526 (10)C17—C161.545 (11)
C2—C31.543 (10)C5—C61.531 (11)
C15—C111.521 (10)C8—C31.514 (10)
C18—C161.532 (10)
C6—S1—C496.6 (3)C13—C14—C16113.2 (5)
C5—S2—C499.6 (4)C9—C14—C16113.7 (6)
C8—O1—C9117.4 (6)N1—C4—C3102.0 (5)
C1—N1—C4109.0 (6)N1—C4—S2109.0 (5)
C1—N1—C7114.2 (6)C3—C4—S2118.4 (5)
C4—N1—C7117.2 (6)N1—C4—S1115.7 (5)
C27—C2—C1115.5 (6)C3—C4—S1105.0 (4)
C27—C2—C3113.0 (6)S2—C4—S1107.1 (4)
C1—C2—C3101.6 (6)C2—C27—Fe1129.1 (5)
C20—C19—C16122.3 (7)O2—C8—O1124.1 (7)
C24—C19—C16120.8 (6)O2—C8—C3124.7 (7)
C14—C13—C12112.6 (6)O1—C8—C3111.2 (6)
C11—C10—C9112.7 (6)C8—C3—C2111.4 (6)
O1—C9—C10106.6 (5)C8—C3—C4113.6 (6)
O1—C9—C14110.4 (6)C2—C3—C4105.5 (5)
C10—C9—C14111.8 (6)N1—C1—C2102.3 (6)
C11—C12—C13111.8 (6)C5—C6—S1106.0 (6)
C13—C14—C9107.1 (6)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds