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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m679.
Published online 2010 May 22. doi:  10.1107/S1600536810017605
PMCID: PMC2979593

Ferrocene-1-carbaldehyde thio­semi­carbazone

Abstract

The asymmetric unit of the title compound, [Fe(C5H5)(C7H8N3S)], consists of two crystallographically independent mol­ecules, A and B. The cyclo­penta­dienyl (Cp) rings in both mol­ecules adopt an eclipsed conformation and are parallel to each other, forming dihedral angles of 2.5 (3) and 1.1 (3)°, respectively. The mean plane of the semicarbazone group is coplanar with the attached Cp ring in mol­ecule A, whereas it is twisted away in mol­ecule B. In the crystal structure, inter­molecular N—H(...)S hydrogen bonds link the mol­ecules into two-dimensional planes parallel to the ab plane. The structure is further consolidated by C—H(...)π inter­actions.

Related literature

For related structures, see: Vikneswaran et al. (2009 [triangle]). For the synthesis of the title compound, see: Mariño et al. (2006 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m679-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C7H8N3S)]
  • M r = 287.16
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m679-efi1.jpg
  • a = 5.8390 (1) Å
  • b = 12.7092 (3) Å
  • c = 16.7675 (4) Å
  • α = 94.447 (2)°
  • β = 97.965 (2)°
  • γ = 97.639 (2)°
  • V = 1215.51 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.39 mm−1
  • T = 100 K
  • 0.30 × 0.11 × 0.05 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.681, T max = 0.929
  • 24408 measured reflections
  • 5589 independent reflections
  • 4024 reflections with I > 2σ(I)
  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.169
  • S = 1.07
  • 5589 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 1.77 e Å−3
  • Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017605/rz2447sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017605/rz2447Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF thanks Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY thanks USM for the award of a USM Fellowship.

supplementary crystallographic information

Comment

As a continuation of our research related to ferrocenyl thiosemicarbazones and their metal complexes, herein we report the crystal structure of formylferrocene thiosemicarbazone.

The asymmetric unit of title compound consists of two crystallographically independent molecules, A and B (Fig. 1). The geometric parameter are comparable to those observed in a closely related structure (Vikneswaran et al., 2009). The Cp rings of each ferrocene residue are parallel, with dihedral angles of Cp1/Cp2 [C1A–C5A/C6A–C10A] = 2.5 (3)° and Cp3/Cp4 [C1B–C5B/C6B–C10B] = 1.1 (3)°. The Cp rings in both molecules adopt an eclipsed conformation [average torsion angles for C–Cg–Cg–C being 2.83 and 3.92°]. The mean plane of the semicarbazone group is coplanar with the attached Cp2 ring in molecule A, whereas the mean plane of semicarbazone group is twisted away from the attached Cp4 ring in molecule B with the dihedral angles between the mean plane and the Cp ring of 4.4 (2) and 33.3 (2)° respectively.

In the crystal structure, intermolecular N—H···S hydrogen bonds (Table 1) link the molecules into two-dimensional layers parallel to ab plane (Fig. 2). The crystal structure is further consolidated by C7A—H7AA···Cg1 interactions.

Experimental

Formylferrocene thiosemicarbazone was prepared as described by Mariño et al. (2006). The single crystals were grown from an aqueous ethanol solution at room temperature in the dark.

Refinement

All H-atoms were placed in calculated positions, with C–H = 0.93–0.98 Å and N–H = 0.86 Å and refined using a riding model, with Uiso(H) = 1.2 Ueq(C, N). The highest residual density peak is located 1.06 Å from atom Fe1B and the deepest hole is located 0.75 Å from atom Fe1A.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis, showing 2-D layers parallel to ab plane. Hydrogen atoms not involved in hydrogen-bonding (dashed lines) are omitted for clarity.

Crystal data

[Fe(C5H5)(C7H8N3S)]Z = 4
Mr = 287.16F(000) = 592
Triclinic, P1Dx = 1.569 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8390 (1) ÅCell parameters from 3248 reflections
b = 12.7092 (3) Åθ = 2.3–30.0°
c = 16.7675 (4) ŵ = 1.39 mm1
α = 94.447 (2)°T = 100 K
β = 97.965 (2)°Block, brown
γ = 97.639 (2)°0.30 × 0.11 × 0.05 mm
V = 1215.51 (5) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer5589 independent reflections
Radiation source: fine-focus sealed tube4024 reflections with I > 2σ(I)
graphiteRint = 0.087
[var phi] and ω scansθmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −7→7
Tmin = 0.681, Tmax = 0.929k = −16→16
24408 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0849P)2 + 1.4801P] where P = (Fo2 + 2Fc2)/3
5589 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 1.77 e Å3
0 restraintsΔρmin = −0.53 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(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)

xyzUiso*/Ueq
Fe1A0.01430 (12)0.26161 (5)0.31434 (4)0.01472 (18)
S1A0.3946 (2)−0.15030 (10)0.01954 (8)0.0197 (3)
N1A0.0969 (7)0.0658 (3)0.1302 (2)0.0172 (9)
N2A0.2533 (7)0.0155 (3)0.0929 (2)0.0184 (9)
H2AB0.38700.05000.08820.022*
N3A−0.0087 (7)−0.1375 (3)0.0736 (2)0.0198 (9)
H3AB−0.1016−0.10400.09800.024*
H3AC−0.0498−0.20360.05570.024*
C1A−0.0588 (9)0.2347 (4)0.4275 (3)0.0212 (11)
H1AA−0.21250.23060.44520.025*
C2A0.0402 (9)0.1482 (4)0.3940 (3)0.0194 (10)
H2AA−0.03510.07380.38390.023*
C3A0.2645 (9)0.1878 (4)0.3766 (3)0.0202 (11)
H3AA0.37160.14580.35280.024*
C4A0.3071 (9)0.3000 (4)0.4004 (3)0.0199 (11)
H4AA0.44830.34880.39570.024*
C5A0.1068 (10)0.3281 (4)0.4308 (3)0.0235 (11)
H5AA0.08590.40010.45090.028*
C6A0.0681 (9)0.3422 (4)0.2154 (3)0.0187 (10)
H6AA0.21150.38810.20870.022*
C7A−0.1234 (9)0.3749 (4)0.2508 (3)0.0198 (11)
H7AA−0.13480.44760.27250.024*
C8A−0.2945 (9)0.2840 (4)0.2488 (3)0.0204 (11)
H8AA−0.44400.28310.26920.024*
C9A−0.2107 (9)0.1940 (4)0.2135 (3)0.0204 (11)
H9AA−0.29240.12060.20530.024*
C10A0.0119 (9)0.2293 (4)0.1916 (3)0.0176 (10)
C11A0.1600 (9)0.1663 (4)0.1515 (3)0.0176 (10)
H11A0.30340.19900.14090.021*
C12A0.1969 (8)−0.0878 (4)0.0638 (3)0.0164 (10)
Fe1B0.31852 (12)0.76679 (5)0.33898 (4)0.01544 (19)
S1B0.8033 (2)0.62803 (10)−0.02897 (7)0.0184 (3)
N1B0.4716 (7)0.6003 (3)0.1573 (2)0.0165 (8)
N2B0.5307 (7)0.6233 (3)0.0826 (2)0.0171 (9)
H2BB0.45540.66510.05470.021*
N3B0.7899 (7)0.5037 (3)0.0921 (2)0.0197 (9)
H3BB0.73440.48270.13400.024*
H3BC0.90130.47470.07500.024*
C1B0.6319 (9)0.8646 (4)0.3469 (3)0.0240 (11)
H1BA0.78360.84110.34320.029*
C2B0.4734 (9)0.8886 (4)0.2811 (3)0.0239 (11)
H2BA0.49620.88430.22420.029*
C3B0.2759 (10)0.9180 (4)0.3118 (3)0.0249 (12)
H3BA0.13790.93860.28000.030*
C4B0.3125 (10)0.9134 (4)0.3974 (3)0.0238 (11)
H4BA0.20490.93060.43480.029*
C5B0.5345 (9)0.8807 (4)0.4187 (3)0.0230 (11)
H5BA0.60680.87080.47330.028*
C6B0.0264 (8)0.6671 (4)0.2828 (3)0.0160 (10)
H6BA−0.10640.68780.24820.019*
C7B0.0491 (9)0.6626 (4)0.3678 (3)0.0196 (10)
H7BA−0.06510.68080.40230.024*
C8B0.2653 (9)0.6287 (4)0.3946 (3)0.0180 (10)
H8BA0.32610.61970.45070.022*
C9B0.3813 (9)0.6118 (4)0.3270 (3)0.0160 (10)
H9BA0.53450.58800.32770.019*
C10B0.2328 (8)0.6359 (4)0.2570 (3)0.0165 (10)
C11B0.2939 (9)0.6408 (4)0.1760 (3)0.0168 (10)
H11B0.20400.67330.13760.020*
C12B0.7035 (8)0.5809 (4)0.0537 (3)0.0145 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe1A0.0161 (4)0.0153 (4)0.0130 (3)0.0028 (3)0.0020 (3)0.0026 (3)
S1A0.0174 (6)0.0182 (6)0.0271 (6)0.0065 (5)0.0101 (5)0.0059 (5)
N1A0.015 (2)0.019 (2)0.019 (2)0.0050 (17)0.0053 (17)0.0022 (16)
N2A0.016 (2)0.018 (2)0.022 (2)0.0024 (17)0.0038 (17)0.0039 (17)
N3A0.014 (2)0.020 (2)0.024 (2)0.0008 (18)0.0059 (17)−0.0045 (17)
C1A0.022 (3)0.030 (3)0.013 (2)0.005 (2)0.005 (2)0.006 (2)
C2A0.022 (3)0.019 (2)0.018 (2)0.004 (2)0.000 (2)0.0065 (19)
C3A0.019 (3)0.024 (3)0.018 (2)0.006 (2)0.000 (2)0.003 (2)
C4A0.015 (2)0.025 (3)0.017 (2)−0.003 (2)−0.0027 (19)0.003 (2)
C5A0.032 (3)0.027 (3)0.013 (2)0.009 (2)0.003 (2)0.003 (2)
C6A0.025 (3)0.017 (2)0.015 (2)0.005 (2)0.003 (2)0.0057 (18)
C7A0.026 (3)0.020 (2)0.016 (2)0.011 (2)0.004 (2)0.0047 (19)
C8A0.019 (3)0.027 (3)0.015 (2)0.007 (2)0.002 (2)0.000 (2)
C9A0.018 (3)0.023 (3)0.019 (2)0.004 (2)0.000 (2)0.000 (2)
C10A0.020 (3)0.017 (2)0.014 (2)0.000 (2)0.0013 (19)0.0034 (18)
C11A0.016 (2)0.022 (3)0.016 (2)0.004 (2)0.0033 (19)0.0053 (19)
C12A0.013 (2)0.020 (2)0.017 (2)0.000 (2)0.0042 (19)0.0040 (19)
Fe1B0.0157 (4)0.0154 (4)0.0150 (3)0.0021 (3)0.0022 (3)0.0008 (3)
S1B0.0210 (6)0.0173 (6)0.0186 (6)0.0033 (5)0.0078 (5)0.0030 (5)
N1B0.018 (2)0.015 (2)0.0164 (19)0.0006 (17)0.0045 (17)0.0016 (15)
N2B0.017 (2)0.017 (2)0.020 (2)0.0065 (17)0.0082 (17)0.0051 (16)
N3B0.019 (2)0.022 (2)0.021 (2)0.0073 (18)0.0076 (17)0.0045 (17)
C1B0.019 (3)0.014 (2)0.037 (3)−0.002 (2)0.002 (2)0.001 (2)
C2B0.026 (3)0.019 (3)0.027 (3)−0.002 (2)0.009 (2)0.006 (2)
C3B0.025 (3)0.020 (3)0.029 (3)0.001 (2)−0.001 (2)0.006 (2)
C4B0.028 (3)0.017 (2)0.027 (3)0.003 (2)0.009 (2)−0.001 (2)
C5B0.027 (3)0.014 (2)0.024 (3)−0.001 (2)−0.004 (2)−0.001 (2)
C6B0.013 (2)0.015 (2)0.020 (2)0.0012 (19)0.0028 (19)0.0029 (18)
C7B0.018 (3)0.018 (2)0.021 (2)−0.005 (2)0.005 (2)−0.0033 (19)
C8B0.019 (2)0.015 (2)0.021 (2)0.001 (2)0.005 (2)0.0024 (19)
C9B0.017 (2)0.013 (2)0.018 (2)0.0013 (19)0.0021 (19)0.0001 (18)
C10B0.017 (2)0.015 (2)0.018 (2)−0.0007 (19)0.0049 (19)0.0030 (18)
C11B0.018 (2)0.014 (2)0.017 (2)−0.002 (2)−0.0010 (19)0.0013 (18)
C12B0.014 (2)0.014 (2)0.014 (2)0.0012 (19)0.0000 (18)−0.0002 (17)

Geometric parameters (Å, °)

Fe1A—C5A2.036 (5)Fe1B—C10B2.034 (5)
Fe1A—C7A2.040 (5)Fe1B—C4B2.043 (5)
Fe1A—C8A2.043 (5)Fe1B—C6B2.048 (5)
Fe1A—C9A2.045 (5)Fe1B—C3B2.049 (5)
Fe1A—C2A2.045 (5)Fe1B—C9B2.051 (5)
Fe1A—C1A2.045 (5)Fe1B—C1B2.053 (5)
Fe1A—C3A2.049 (5)Fe1B—C7B2.054 (5)
Fe1A—C6A2.054 (5)Fe1B—C5B2.054 (5)
Fe1A—C4A2.057 (5)Fe1B—C8B2.058 (5)
Fe1A—C10A2.065 (5)Fe1B—C2B2.064 (5)
S1A—C12A1.704 (5)S1B—C12B1.697 (5)
N1A—C11A1.289 (6)N1B—C11B1.283 (6)
N1A—N2A1.373 (5)N1B—N2B1.386 (5)
N2A—C12A1.346 (6)N2B—C12B1.336 (6)
N2A—H2AB0.8600N2B—H2BB0.8600
N3A—C12A1.318 (6)N3B—C12B1.331 (6)
N3A—H3AB0.8600N3B—H3BB0.8600
N3A—H3AC0.8600N3B—H3BC0.8600
C1A—C5A1.419 (8)C1B—C5B1.413 (8)
C1A—C2A1.422 (7)C1B—C2B1.417 (7)
C1A—H1AA0.9800C1B—H1BA0.9800
C2A—C3A1.416 (7)C2B—C3B1.408 (8)
C2A—H2AA0.9800C2B—H2BA0.9800
C3A—C4A1.430 (7)C3B—C4B1.429 (7)
C3A—H3AA0.9800C3B—H3BA0.9800
C4A—C5A1.415 (7)C4B—C5B1.420 (7)
C4A—H4AA0.9800C4B—H4BA0.9800
C5A—H5AA0.9800C5B—H5BA0.9800
C6A—C7A1.430 (7)C6B—C7B1.420 (7)
C6A—C10A1.440 (7)C6B—C10B1.429 (7)
C6A—H6AA0.9800C6B—H6BA0.9800
C7A—C8A1.418 (7)C7B—C8B1.413 (7)
C7A—H7AA0.9800C7B—H7BA0.9800
C8A—C9A1.423 (7)C8B—C9B1.416 (7)
C8A—H8AA0.9800C8B—H8BA0.9800
C9A—C10A1.424 (7)C9B—C10B1.437 (6)
C9A—H9AA0.9800C9B—H9BA0.9800
C10A—C11A1.450 (7)C10B—C11B1.456 (7)
C11A—H11A0.9300C11B—H11B0.9300
C5A—Fe1A—C7A106.2 (2)C10B—Fe1B—C4B160.8 (2)
C5A—Fe1A—C8A120.3 (2)C10B—Fe1B—C6B40.97 (19)
C7A—Fe1A—C8A40.6 (2)C4B—Fe1B—C6B124.1 (2)
C5A—Fe1A—C9A156.0 (2)C10B—Fe1B—C3B123.6 (2)
C7A—Fe1A—C9A68.7 (2)C4B—Fe1B—C3B40.9 (2)
C8A—Fe1A—C9A40.72 (19)C6B—Fe1B—C3B107.1 (2)
C5A—Fe1A—C2A68.2 (2)C10B—Fe1B—C9B41.19 (18)
C7A—Fe1A—C2A159.1 (2)C4B—Fe1B—C9B156.8 (2)
C8A—Fe1A—C2A123.3 (2)C6B—Fe1B—C9B68.92 (19)
C9A—Fe1A—C2A107.7 (2)C3B—Fe1B—C9B160.8 (2)
C5A—Fe1A—C1A40.7 (2)C10B—Fe1B—C1B121.3 (2)
C7A—Fe1A—C1A122.1 (2)C4B—Fe1B—C1B68.0 (2)
C8A—Fe1A—C1A105.8 (2)C6B—Fe1B—C1B156.5 (2)
C9A—Fe1A—C1A120.7 (2)C3B—Fe1B—C1B67.7 (2)
C2A—Fe1A—C1A40.7 (2)C9B—Fe1B—C1B108.0 (2)
C5A—Fe1A—C3A68.4 (2)C10B—Fe1B—C7B68.31 (19)
C7A—Fe1A—C3A158.1 (2)C4B—Fe1B—C7B108.2 (2)
C8A—Fe1A—C3A160.6 (2)C6B—Fe1B—C7B40.49 (18)
C9A—Fe1A—C3A124.9 (2)C3B—Fe1B—C7B121.8 (2)
C2A—Fe1A—C3A40.5 (2)C9B—Fe1B—C7B68.1 (2)
C1A—Fe1A—C3A68.5 (2)C1B—Fe1B—C7B161.8 (2)
C5A—Fe1A—C6A123.7 (2)C10B—Fe1B—C5B156.8 (2)
C7A—Fe1A—C6A40.89 (19)C4B—Fe1B—C5B40.6 (2)
C8A—Fe1A—C6A68.5 (2)C6B—Fe1B—C5B161.3 (2)
C9A—Fe1A—C6A68.8 (2)C3B—Fe1B—C5B68.2 (2)
C2A—Fe1A—C6A158.8 (2)C9B—Fe1B—C5B121.6 (2)
C1A—Fe1A—C6A159.4 (2)C1B—Fe1B—C5B40.3 (2)
C3A—Fe1A—C6A123.2 (2)C7B—Fe1B—C5B125.3 (2)
C5A—Fe1A—C4A40.5 (2)C10B—Fe1B—C8B68.31 (19)
C7A—Fe1A—C4A121.5 (2)C4B—Fe1B—C8B122.1 (2)
C8A—Fe1A—C4A156.3 (2)C6B—Fe1B—C8B68.15 (19)
C9A—Fe1A—C4A162.1 (2)C3B—Fe1B—C8B157.3 (2)
C2A—Fe1A—C4A68.2 (2)C9B—Fe1B—C8B40.31 (19)
C1A—Fe1A—C4A68.4 (2)C1B—Fe1B—C8B125.5 (2)
C3A—Fe1A—C4A40.8 (2)C7B—Fe1B—C8B40.21 (19)
C6A—Fe1A—C4A108.4 (2)C5B—Fe1B—C8B108.8 (2)
C5A—Fe1A—C10A161.4 (2)C10B—Fe1B—C2B107.3 (2)
C7A—Fe1A—C10A68.63 (19)C4B—Fe1B—C2B68.0 (2)
C8A—Fe1A—C10A68.21 (19)C6B—Fe1B—C2B121.0 (2)
C9A—Fe1A—C10A40.5 (2)C3B—Fe1B—C2B40.0 (2)
C2A—Fe1A—C10A122.9 (2)C9B—Fe1B—C2B124.7 (2)
C1A—Fe1A—C10A157.2 (2)C1B—Fe1B—C2B40.3 (2)
C3A—Fe1A—C10A109.4 (2)C7B—Fe1B—C2B156.6 (2)
C6A—Fe1A—C10A40.94 (18)C5B—Fe1B—C2B67.8 (2)
C4A—Fe1A—C10A125.8 (2)C8B—Fe1B—C2B161.6 (2)
C11A—N1A—N2A115.4 (4)C11B—N1B—N2B114.4 (4)
C12A—N2A—N1A119.9 (4)C12B—N2B—N1B120.5 (4)
C12A—N2A—H2AB120.0C12B—N2B—H2BB119.7
N1A—N2A—H2AB120.0N1B—N2B—H2BB119.7
C12A—N3A—H3AB120.0C12B—N3B—H3BB120.0
C12A—N3A—H3AC120.0C12B—N3B—H3BC120.0
H3AB—N3A—H3AC120.0H3BB—N3B—H3BC120.0
C5A—C1A—C2A107.3 (5)C5B—C1B—C2B108.4 (5)
C5A—C1A—Fe1A69.3 (3)C5B—C1B—Fe1B69.9 (3)
C2A—C1A—Fe1A69.7 (3)C2B—C1B—Fe1B70.3 (3)
C5A—C1A—H1AA126.4C5B—C1B—H1BA125.8
C2A—C1A—H1AA126.4C2B—C1B—H1BA125.8
Fe1A—C1A—H1AA126.4Fe1B—C1B—H1BA125.8
C3A—C2A—C1A108.6 (5)C3B—C2B—C1B108.0 (5)
C3A—C2A—Fe1A69.9 (3)C3B—C2B—Fe1B69.4 (3)
C1A—C2A—Fe1A69.7 (3)C1B—C2B—Fe1B69.4 (3)
C3A—C2A—H2AA125.7C3B—C2B—H2BA126.0
C1A—C2A—H2AA125.7C1B—C2B—H2BA126.0
Fe1A—C2A—H2AA125.7Fe1B—C2B—H2BA126.0
C2A—C3A—C4A107.7 (4)C2B—C3B—C4B108.1 (5)
C2A—C3A—Fe1A69.6 (3)C2B—C3B—Fe1B70.6 (3)
C4A—C3A—Fe1A69.9 (3)C4B—C3B—Fe1B69.4 (3)
C2A—C3A—H3AA126.1C2B—C3B—H3BA126.0
C4A—C3A—H3AA126.1C4B—C3B—H3BA126.0
Fe1A—C3A—H3AA126.1Fe1B—C3B—H3BA126.0
C5A—C4A—C3A107.6 (5)C5B—C4B—C3B107.6 (5)
C5A—C4A—Fe1A69.0 (3)C5B—C4B—Fe1B70.1 (3)
C3A—C4A—Fe1A69.3 (3)C3B—C4B—Fe1B69.8 (3)
C5A—C4A—H4AA126.2C5B—C4B—H4BA126.2
C3A—C4A—H4AA126.2C3B—C4B—H4BA126.2
Fe1A—C4A—H4AA126.2Fe1B—C4B—H4BA126.2
C4A—C5A—C1A108.8 (5)C1B—C5B—C4B107.8 (5)
C4A—C5A—Fe1A70.5 (3)C1B—C5B—Fe1B69.8 (3)
C1A—C5A—Fe1A70.0 (3)C4B—C5B—Fe1B69.3 (3)
C4A—C5A—H5AA125.6C1B—C5B—H5BA126.1
C1A—C5A—H5AA125.6C4B—C5B—H5BA126.1
Fe1A—C5A—H5AA125.6Fe1B—C5B—H5BA126.1
C7A—C6A—C10A107.5 (5)C7B—C6B—C10B107.4 (4)
C7A—C6A—Fe1A69.0 (3)C7B—C6B—Fe1B70.0 (3)
C10A—C6A—Fe1A69.9 (3)C10B—C6B—Fe1B69.0 (3)
C7A—C6A—H6AA126.3C7B—C6B—H6BA126.3
C10A—C6A—H6AA126.3C10B—C6B—H6BA126.3
Fe1A—C6A—H6AA126.3Fe1B—C6B—H6BA126.3
C8A—C7A—C6A108.1 (4)C8B—C7B—C6B108.6 (4)
C8A—C7A—Fe1A69.8 (3)C8B—C7B—Fe1B70.1 (3)
C6A—C7A—Fe1A70.1 (3)C6B—C7B—Fe1B69.5 (3)
C8A—C7A—H7AA125.9C8B—C7B—H7BA125.7
C6A—C7A—H7AA125.9C6B—C7B—H7BA125.7
Fe1A—C7A—H7AA125.9Fe1B—C7B—H7BA125.7
C7A—C8A—C9A108.5 (4)C7B—C8B—C9B108.7 (4)
C7A—C8A—Fe1A69.6 (3)C7B—C8B—Fe1B69.7 (3)
C9A—C8A—Fe1A69.7 (3)C9B—C8B—Fe1B69.6 (3)
C7A—C8A—H8AA125.7C7B—C8B—H8BA125.7
C9A—C8A—H8AA125.7C9B—C8B—H8BA125.7
Fe1A—C8A—H8AA125.7Fe1B—C8B—H8BA125.7
C8A—C9A—C10A108.1 (5)C8B—C9B—C10B107.3 (4)
C8A—C9A—Fe1A69.6 (3)C8B—C9B—Fe1B70.1 (3)
C10A—C9A—Fe1A70.5 (3)C10B—C9B—Fe1B68.8 (3)
C8A—C9A—H9AA126.0C8B—C9B—H9BA126.4
C10A—C9A—H9AA126.0C10B—C9B—H9BA126.4
Fe1A—C9A—H9AA126.0Fe1B—C9B—H9BA126.4
C9A—C10A—C6A107.8 (4)C6B—C10B—C9B108.1 (4)
C9A—C10A—C11A127.7 (5)C6B—C10B—C11B125.6 (4)
C6A—C10A—C11A124.4 (5)C9B—C10B—C11B125.9 (4)
C9A—C10A—Fe1A69.0 (3)C6B—C10B—Fe1B70.0 (3)
C6A—C10A—Fe1A69.1 (3)C9B—C10B—Fe1B70.0 (3)
C11A—C10A—Fe1A128.0 (3)C11B—C10B—Fe1B119.8 (3)
N1A—C11A—C10A121.3 (5)N1B—C11B—C10B120.1 (4)
N1A—C11A—H11A119.4N1B—C11B—H11B119.9
C10A—C11A—H11A119.4C10B—C11B—H11B119.9
N3A—C12A—N2A117.7 (4)N3B—C12B—N2B117.7 (4)
N3A—C12A—S1A122.7 (4)N3B—C12B—S1B123.3 (4)
N2A—C12A—S1A119.6 (4)N2B—C12B—S1B118.9 (3)
C11A—N1A—N2A—C12A−175.7 (4)C11B—N1B—N2B—C12B−176.0 (4)
C7A—Fe1A—C1A—C5A−77.1 (4)C10B—Fe1B—C1B—C5B−161.2 (3)
C8A—Fe1A—C1A—C5A−118.3 (3)C4B—Fe1B—C1B—C5B37.8 (3)
C9A—Fe1A—C1A—C5A−159.9 (3)C6B—Fe1B—C1B—C5B163.7 (4)
C2A—Fe1A—C1A—C5A118.6 (4)C3B—Fe1B—C1B—C5B82.1 (3)
C3A—Fe1A—C1A—C5A81.4 (3)C9B—Fe1B—C1B—C5B−117.9 (3)
C6A—Fe1A—C1A—C5A−47.4 (7)C7B—Fe1B—C1B—C5B−43.4 (8)
C4A—Fe1A—C1A—C5A37.4 (3)C8B—Fe1B—C1B—C5B−76.7 (4)
C10A—Fe1A—C1A—C5A170.4 (5)C2B—Fe1B—C1B—C5B119.3 (4)
C5A—Fe1A—C1A—C2A−118.6 (4)C10B—Fe1B—C1B—C2B79.6 (3)
C7A—Fe1A—C1A—C2A164.3 (3)C4B—Fe1B—C1B—C2B−81.5 (3)
C8A—Fe1A—C1A—C2A123.1 (3)C6B—Fe1B—C1B—C2B44.4 (6)
C9A—Fe1A—C1A—C2A81.5 (3)C3B—Fe1B—C1B—C2B−37.2 (3)
C3A—Fe1A—C1A—C2A−37.2 (3)C9B—Fe1B—C1B—C2B122.8 (3)
C6A—Fe1A—C1A—C2A−166.0 (5)C7B—Fe1B—C1B—C2B−162.6 (6)
C4A—Fe1A—C1A—C2A−81.2 (3)C5B—Fe1B—C1B—C2B−119.3 (4)
C10A—Fe1A—C1A—C2A51.8 (6)C8B—Fe1B—C1B—C2B164.0 (3)
C5A—C1A—C2A—C3A−0.1 (5)C5B—C1B—C2B—C3B−0.9 (6)
Fe1A—C1A—C2A—C3A59.3 (3)Fe1B—C1B—C2B—C3B58.9 (4)
C5A—C1A—C2A—Fe1A−59.3 (3)C5B—C1B—C2B—Fe1B−59.7 (4)
C5A—Fe1A—C2A—C3A−81.8 (3)C10B—Fe1B—C2B—C3B122.0 (3)
C7A—Fe1A—C2A—C3A−160.0 (5)C4B—Fe1B—C2B—C3B−38.1 (3)
C8A—Fe1A—C2A—C3A165.5 (3)C6B—Fe1B—C2B—C3B79.4 (4)
C9A—Fe1A—C2A—C3A123.4 (3)C9B—Fe1B—C2B—C3B164.0 (3)
C1A—Fe1A—C2A—C3A−119.9 (4)C1B—Fe1B—C2B—C3B−119.6 (5)
C6A—Fe1A—C2A—C3A46.5 (7)C7B—Fe1B—C2B—C3B46.9 (6)
C4A—Fe1A—C2A—C3A−38.0 (3)C5B—Fe1B—C2B—C3B−82.1 (3)
C10A—Fe1A—C2A—C3A81.4 (3)C8B—Fe1B—C2B—C3B−164.9 (6)
C5A—Fe1A—C2A—C1A38.1 (3)C10B—Fe1B—C2B—C1B−118.4 (3)
C7A—Fe1A—C2A—C1A−40.1 (7)C4B—Fe1B—C2B—C1B81.4 (3)
C8A—Fe1A—C2A—C1A−74.7 (4)C6B—Fe1B—C2B—C1B−161.0 (3)
C9A—Fe1A—C2A—C1A−116.8 (3)C3B—Fe1B—C2B—C1B119.6 (5)
C3A—Fe1A—C2A—C1A119.9 (4)C9B—Fe1B—C2B—C1B−76.4 (4)
C6A—Fe1A—C2A—C1A166.4 (5)C7B—Fe1B—C2B—C1B166.5 (5)
C4A—Fe1A—C2A—C1A81.8 (3)C5B—Fe1B—C2B—C1B37.5 (3)
C10A—Fe1A—C2A—C1A−158.7 (3)C8B—Fe1B—C2B—C1B−45.3 (8)
C1A—C2A—C3A—C4A0.6 (5)C1B—C2B—C3B—C4B0.6 (6)
Fe1A—C2A—C3A—C4A59.8 (3)Fe1B—C2B—C3B—C4B59.4 (4)
C1A—C2A—C3A—Fe1A−59.1 (3)C1B—C2B—C3B—Fe1B−58.9 (4)
C5A—Fe1A—C3A—C2A81.3 (3)C10B—Fe1B—C3B—C2B−76.3 (4)
C7A—Fe1A—C3A—C2A160.9 (5)C4B—Fe1B—C3B—C2B119.0 (5)
C8A—Fe1A—C3A—C2A−39.0 (7)C6B—Fe1B—C3B—C2B−118.2 (3)
C9A—Fe1A—C3A—C2A−75.8 (4)C9B—Fe1B—C3B—C2B−43.4 (8)
C1A—Fe1A—C3A—C2A37.4 (3)C1B—Fe1B—C3B—C2B37.4 (3)
C6A—Fe1A—C3A—C2A−161.7 (3)C7B—Fe1B—C3B—C2B−160.0 (3)
C4A—Fe1A—C3A—C2A118.8 (4)C5B—Fe1B—C3B—C2B81.0 (3)
C10A—Fe1A—C3A—C2A−118.3 (3)C8B—Fe1B—C3B—C2B167.7 (5)
C5A—Fe1A—C3A—C4A−37.5 (3)C10B—Fe1B—C3B—C4B164.7 (3)
C7A—Fe1A—C3A—C4A42.1 (7)C6B—Fe1B—C3B—C4B122.8 (3)
C8A—Fe1A—C3A—C4A−157.8 (5)C9B—Fe1B—C3B—C4B−162.4 (6)
C9A—Fe1A—C3A—C4A165.4 (3)C1B—Fe1B—C3B—C4B−81.6 (3)
C2A—Fe1A—C3A—C4A−118.8 (4)C7B—Fe1B—C3B—C4B81.0 (4)
C1A—Fe1A—C3A—C4A−81.4 (3)C5B—Fe1B—C3B—C4B−38.0 (3)
C6A—Fe1A—C3A—C4A79.5 (3)C8B—Fe1B—C3B—C4B48.7 (7)
C10A—Fe1A—C3A—C4A122.8 (3)C2B—Fe1B—C3B—C4B−119.0 (5)
C2A—C3A—C4A—C5A−1.0 (5)C2B—C3B—C4B—C5B0.0 (6)
Fe1A—C3A—C4A—C5A58.6 (3)Fe1B—C3B—C4B—C5B60.2 (3)
C2A—C3A—C4A—Fe1A−59.6 (3)C2B—C3B—C4B—Fe1B−60.2 (4)
C7A—Fe1A—C4A—C5A77.7 (4)C10B—Fe1B—C4B—C5B−160.3 (6)
C8A—Fe1A—C4A—C5A42.5 (6)C6B—Fe1B—C4B—C5B165.5 (3)
C9A—Fe1A—C4A—C5A−161.6 (6)C3B—Fe1B—C4B—C5B−118.5 (5)
C2A—Fe1A—C4A—C5A−81.5 (3)C9B—Fe1B—C4B—C5B46.9 (7)
C1A—Fe1A—C4A—C5A−37.6 (3)C1B—Fe1B—C4B—C5B−37.5 (3)
C3A—Fe1A—C4A—C5A−119.3 (4)C7B—Fe1B—C4B—C5B123.6 (3)
C6A—Fe1A—C4A—C5A120.7 (3)C8B—Fe1B—C4B—C5B81.6 (4)
C10A—Fe1A—C4A—C5A162.8 (3)C2B—Fe1B—C4B—C5B−81.1 (3)
C5A—Fe1A—C4A—C3A119.3 (4)C10B—Fe1B—C4B—C3B−41.9 (8)
C7A—Fe1A—C4A—C3A−163.0 (3)C6B—Fe1B—C4B—C3B−76.1 (4)
C8A—Fe1A—C4A—C3A161.8 (5)C9B—Fe1B—C4B—C3B165.4 (5)
C9A—Fe1A—C4A—C3A−42.2 (8)C1B—Fe1B—C4B—C3B81.0 (3)
C2A—Fe1A—C4A—C3A37.8 (3)C7B—Fe1B—C4B—C3B−118.0 (3)
C1A—Fe1A—C4A—C3A81.7 (3)C5B—Fe1B—C4B—C3B118.5 (5)
C6A—Fe1A—C4A—C3A−119.9 (3)C8B—Fe1B—C4B—C3B−160.0 (3)
C10A—Fe1A—C4A—C3A−77.8 (4)C2B—Fe1B—C4B—C3B37.4 (3)
C3A—C4A—C5A—C1A0.9 (5)C2B—C1B—C5B—C4B0.9 (6)
Fe1A—C4A—C5A—C1A59.8 (3)Fe1B—C1B—C5B—C4B−59.1 (4)
C3A—C4A—C5A—Fe1A−58.8 (3)C2B—C1B—C5B—Fe1B60.0 (4)
C2A—C1A—C5A—C4A−0.5 (5)C3B—C4B—C5B—C1B−0.5 (6)
Fe1A—C1A—C5A—C4A−60.1 (3)Fe1B—C4B—C5B—C1B59.4 (3)
C2A—C1A—C5A—Fe1A59.6 (3)C3B—C4B—C5B—Fe1B−59.9 (4)
C7A—Fe1A—C5A—C4A−119.8 (3)C10B—Fe1B—C5B—C1B44.5 (6)
C8A—Fe1A—C5A—C4A−161.7 (3)C4B—Fe1B—C5B—C1B−119.2 (4)
C9A—Fe1A—C5A—C4A166.1 (5)C6B—Fe1B—C5B—C1B−159.6 (6)
C2A—Fe1A—C5A—C4A81.5 (3)C3B—Fe1B—C5B—C1B−80.9 (3)
C1A—Fe1A—C5A—C4A119.5 (4)C9B—Fe1B—C5B—C1B80.6 (3)
C3A—Fe1A—C5A—C4A37.8 (3)C7B—Fe1B—C5B—C1B164.8 (3)
C6A—Fe1A—C5A—C4A−78.6 (4)C8B—Fe1B—C5B—C1B123.1 (3)
C10A—Fe1A—C5A—C4A−48.8 (7)C2B—Fe1B—C5B—C1B−37.5 (3)
C7A—Fe1A—C5A—C1A120.6 (3)C10B—Fe1B—C5B—C4B163.7 (5)
C8A—Fe1A—C5A—C1A78.8 (3)C6B—Fe1B—C5B—C4B−40.4 (8)
C9A—Fe1A—C5A—C1A46.6 (6)C3B—Fe1B—C5B—C4B38.3 (3)
C2A—Fe1A—C5A—C1A−38.0 (3)C9B—Fe1B—C5B—C4B−160.3 (3)
C3A—Fe1A—C5A—C1A−81.8 (3)C1B—Fe1B—C5B—C4B119.2 (4)
C6A—Fe1A—C5A—C1A161.9 (3)C7B—Fe1B—C5B—C4B−76.1 (4)
C4A—Fe1A—C5A—C1A−119.5 (4)C8B—Fe1B—C5B—C4B−117.7 (3)
C10A—Fe1A—C5A—C1A−168.3 (6)C2B—Fe1B—C5B—C4B81.6 (3)
C5A—Fe1A—C6A—C7A−75.2 (4)C10B—Fe1B—C6B—C7B118.7 (4)
C8A—Fe1A—C6A—C7A37.7 (3)C4B—Fe1B—C6B—C7B−77.7 (3)
C9A—Fe1A—C6A—C7A81.6 (3)C3B—Fe1B—C6B—C7B−119.3 (3)
C2A—Fe1A—C6A—C7A165.9 (5)C9B—Fe1B—C6B—C7B80.5 (3)
C1A—Fe1A—C6A—C7A−39.9 (7)C1B—Fe1B—C6B—C7B167.4 (5)
C3A—Fe1A—C6A—C7A−159.8 (3)C5B—Fe1B—C6B—C7B−47.1 (7)
C4A—Fe1A—C6A—C7A−117.2 (3)C8B—Fe1B—C6B—C7B37.1 (3)
C10A—Fe1A—C6A—C7A118.8 (4)C2B—Fe1B—C6B—C7B−160.8 (3)
C5A—Fe1A—C6A—C10A166.0 (3)C4B—Fe1B—C6B—C10B163.6 (3)
C7A—Fe1A—C6A—C10A−118.8 (4)C3B—Fe1B—C6B—C10B121.9 (3)
C8A—Fe1A—C6A—C10A−81.1 (3)C9B—Fe1B—C6B—C10B−38.2 (3)
C9A—Fe1A—C6A—C10A−37.2 (3)C1B—Fe1B—C6B—C10B48.6 (6)
C2A—Fe1A—C6A—C10A47.1 (7)C7B—Fe1B—C6B—C10B−118.7 (4)
C1A—Fe1A—C6A—C10A−158.7 (5)C5B—Fe1B—C6B—C10B−165.8 (6)
C3A—Fe1A—C6A—C10A81.4 (3)C8B—Fe1B—C6B—C10B−81.6 (3)
C4A—Fe1A—C6A—C10A123.9 (3)C2B—Fe1B—C6B—C10B80.5 (3)
C10A—C6A—C7A—C8A0.0 (5)C10B—C6B—C7B—C8B−0.3 (5)
Fe1A—C6A—C7A—C8A−59.7 (3)Fe1B—C6B—C7B—C8B−59.3 (3)
C10A—C6A—C7A—Fe1A59.6 (3)C10B—C6B—C7B—Fe1B59.1 (3)
C5A—Fe1A—C7A—C8A−117.8 (3)C10B—Fe1B—C7B—C8B81.6 (3)
C9A—Fe1A—C7A—C8A37.4 (3)C4B—Fe1B—C7B—C8B−118.5 (3)
C2A—Fe1A—C7A—C8A−46.6 (7)C6B—Fe1B—C7B—C8B119.9 (4)
C1A—Fe1A—C7A—C8A−76.4 (3)C3B—Fe1B—C7B—C8B−161.4 (3)
C3A—Fe1A—C7A—C8A170.0 (5)C9B—Fe1B—C7B—C8B37.1 (3)
C6A—Fe1A—C7A—C8A119.1 (4)C1B—Fe1B—C7B—C8B−43.9 (8)
C4A—Fe1A—C7A—C8A−159.1 (3)C5B—Fe1B—C7B—C8B−76.9 (3)
C10A—Fe1A—C7A—C8A81.0 (3)C2B—Fe1B—C7B—C8B165.1 (5)
C5A—Fe1A—C7A—C6A123.1 (3)C10B—Fe1B—C7B—C6B−38.2 (3)
C8A—Fe1A—C7A—C6A−119.1 (4)C4B—Fe1B—C7B—C6B121.6 (3)
C9A—Fe1A—C7A—C6A−81.7 (3)C3B—Fe1B—C7B—C6B78.8 (3)
C2A—Fe1A—C7A—C6A−165.7 (5)C9B—Fe1B—C7B—C6B−82.8 (3)
C1A—Fe1A—C7A—C6A164.6 (3)C1B—Fe1B—C7B—C6B−163.8 (6)
C3A—Fe1A—C7A—C6A50.9 (6)C5B—Fe1B—C7B—C6B163.2 (3)
C4A—Fe1A—C7A—C6A81.8 (3)C8B—Fe1B—C7B—C6B−119.9 (4)
C10A—Fe1A—C7A—C6A−38.1 (3)C2B—Fe1B—C7B—C6B45.2 (6)
C6A—C7A—C8A—C9A0.8 (5)C6B—C7B—C8B—C9B0.2 (5)
Fe1A—C7A—C8A—C9A−59.0 (3)Fe1B—C7B—C8B—C9B−58.9 (3)
C6A—C7A—C8A—Fe1A59.8 (3)C6B—C7B—C8B—Fe1B59.0 (3)
C5A—Fe1A—C8A—C7A79.5 (3)C10B—Fe1B—C8B—C7B−81.6 (3)
C9A—Fe1A—C8A—C7A−119.9 (4)C4B—Fe1B—C8B—C7B80.1 (3)
C2A—Fe1A—C8A—C7A161.9 (3)C6B—Fe1B—C8B—C7B−37.4 (3)
C1A—Fe1A—C8A—C7A121.1 (3)C3B—Fe1B—C8B—C7B44.7 (6)
C3A—Fe1A—C8A—C7A−168.8 (5)C9B—Fe1B—C8B—C7B−120.1 (4)
C6A—Fe1A—C8A—C7A−37.9 (3)C1B—Fe1B—C8B—C7B164.6 (3)
C4A—Fe1A—C8A—C7A49.0 (6)C5B—Fe1B—C8B—C7B122.9 (3)
C10A—Fe1A—C8A—C7A−82.1 (3)C2B—Fe1B—C8B—C7B−161.1 (6)
C5A—Fe1A—C8A—C9A−160.6 (3)C10B—Fe1B—C8B—C9B38.5 (3)
C7A—Fe1A—C8A—C9A119.9 (4)C4B—Fe1B—C8B—C9B−159.8 (3)
C2A—Fe1A—C8A—C9A−78.1 (4)C6B—Fe1B—C8B—C9B82.7 (3)
C1A—Fe1A—C8A—C9A−118.9 (3)C3B—Fe1B—C8B—C9B164.8 (5)
C3A—Fe1A—C8A—C9A−48.8 (7)C1B—Fe1B—C8B—C9B−75.3 (4)
C6A—Fe1A—C8A—C9A82.0 (3)C7B—Fe1B—C8B—C9B120.1 (4)
C4A—Fe1A—C8A—C9A168.9 (5)C5B—Fe1B—C8B—C9B−117.0 (3)
C10A—Fe1A—C8A—C9A37.8 (3)C2B—Fe1B—C8B—C9B−41.0 (8)
C7A—C8A—C9A—C10A−1.3 (5)C7B—C8B—C9B—C10B0.0 (5)
Fe1A—C8A—C9A—C10A−60.2 (3)Fe1B—C8B—C9B—C10B−58.9 (3)
C7A—C8A—C9A—Fe1A58.9 (3)C7B—C8B—C9B—Fe1B59.0 (3)
C5A—Fe1A—C9A—C8A44.9 (6)C10B—Fe1B—C9B—C8B−118.7 (4)
C7A—Fe1A—C9A—C8A−37.3 (3)C4B—Fe1B—C9B—C8B48.1 (6)
C2A—Fe1A—C9A—C8A120.9 (3)C6B—Fe1B—C9B—C8B−80.7 (3)
C1A—Fe1A—C9A—C8A78.3 (4)C3B—Fe1B—C9B—C8B−162.0 (6)
C3A—Fe1A—C9A—C8A162.2 (3)C1B—Fe1B—C9B—C8B124.1 (3)
C6A—Fe1A—C9A—C8A−81.3 (3)C7B—Fe1B—C9B—C8B−37.0 (3)
C4A—Fe1A—C9A—C8A−165.4 (6)C5B—Fe1B—C9B—C8B82.0 (3)
C10A—Fe1A—C9A—C8A−118.9 (4)C2B—Fe1B—C9B—C8B165.4 (3)
C5A—Fe1A—C9A—C10A163.7 (5)C4B—Fe1B—C9B—C10B166.7 (5)
C7A—Fe1A—C9A—C10A81.6 (3)C6B—Fe1B—C9B—C10B38.0 (3)
C8A—Fe1A—C9A—C10A118.9 (4)C3B—Fe1B—C9B—C10B−43.4 (7)
C2A—Fe1A—C9A—C10A−120.2 (3)C1B—Fe1B—C9B—C10B−117.3 (3)
C1A—Fe1A—C9A—C10A−162.8 (3)C7B—Fe1B—C9B—C10B81.6 (3)
C3A—Fe1A—C9A—C10A−78.9 (4)C5B—Fe1B—C9B—C10B−159.4 (3)
C6A—Fe1A—C9A—C10A37.6 (3)C8B—Fe1B—C9B—C10B118.7 (4)
C4A—Fe1A—C9A—C10A−46.6 (8)C2B—Fe1B—C9B—C10B−75.9 (3)
C8A—C9A—C10A—C6A1.3 (5)C7B—C6B—C10B—C9B0.3 (5)
Fe1A—C9A—C10A—C6A−58.4 (3)Fe1B—C6B—C10B—C9B60.0 (3)
C8A—C9A—C10A—C11A−177.9 (4)C7B—C6B—C10B—C11B−172.7 (4)
Fe1A—C9A—C10A—C11A122.4 (5)Fe1B—C6B—C10B—C11B−113.0 (5)
C8A—C9A—C10A—Fe1A59.7 (3)C7B—C6B—C10B—Fe1B−59.7 (3)
C7A—C6A—C10A—C9A−0.8 (5)C8B—C9B—C10B—C6B−0.2 (5)
Fe1A—C6A—C10A—C9A58.3 (3)Fe1B—C9B—C10B—C6B−60.0 (3)
C7A—C6A—C10A—C11A178.4 (4)C8B—C9B—C10B—C11B172.8 (5)
Fe1A—C6A—C10A—C11A−122.5 (5)Fe1B—C9B—C10B—C11B113.0 (5)
C7A—C6A—C10A—Fe1A−59.1 (3)C8B—C9B—C10B—Fe1B59.8 (3)
C5A—Fe1A—C10A—C9A−159.0 (6)C4B—Fe1B—C10B—C6B−45.2 (7)
C7A—Fe1A—C10A—C9A−81.8 (3)C3B—Fe1B—C10B—C6B−76.9 (3)
C8A—Fe1A—C10A—C9A−38.0 (3)C9B—Fe1B—C10B—C6B118.9 (4)
C2A—Fe1A—C10A—C9A78.5 (3)C1B—Fe1B—C10B—C6B−159.5 (3)
C1A—Fe1A—C10A—C9A40.9 (6)C7B—Fe1B—C10B—C6B37.8 (3)
C3A—Fe1A—C10A—C9A121.4 (3)C5B—Fe1B—C10B—C6B168.5 (5)
C6A—Fe1A—C10A—C9A−119.8 (4)C8B—Fe1B—C10B—C6B81.2 (3)
C4A—Fe1A—C10A—C9A164.0 (3)C2B—Fe1B—C10B—C6B−117.8 (3)
C5A—Fe1A—C10A—C6A−39.2 (7)C4B—Fe1B—C10B—C9B−164.1 (6)
C7A—Fe1A—C10A—C6A38.0 (3)C6B—Fe1B—C10B—C9B−118.9 (4)
C8A—Fe1A—C10A—C6A81.9 (3)C3B—Fe1B—C10B—C9B164.3 (3)
C9A—Fe1A—C10A—C6A119.8 (4)C1B—Fe1B—C10B—C9B81.6 (3)
C2A—Fe1A—C10A—C6A−161.6 (3)C7B—Fe1B—C10B—C9B−81.1 (3)
C1A—Fe1A—C10A—C6A160.8 (5)C5B—Fe1B—C10B—C9B49.6 (6)
C3A—Fe1A—C10A—C6A−118.7 (3)C8B—Fe1B—C10B—C9B−37.7 (3)
C4A—Fe1A—C10A—C6A−76.2 (4)C2B—Fe1B—C10B—C9B123.4 (3)
C5A—Fe1A—C10A—C11A78.9 (8)C4B—Fe1B—C10B—C11B75.1 (8)
C7A—Fe1A—C10A—C11A156.0 (5)C6B—Fe1B—C10B—C11B120.4 (5)
C8A—Fe1A—C10A—C11A−160.1 (5)C3B—Fe1B—C10B—C11B43.5 (5)
C9A—Fe1A—C10A—C11A−122.1 (6)C9B—Fe1B—C10B—C11B−120.8 (5)
C2A—Fe1A—C10A—C11A−43.6 (5)C1B—Fe1B—C10B—C11B−39.1 (5)
C1A—Fe1A—C10A—C11A−81.2 (7)C7B—Fe1B—C10B—C11B158.2 (4)
C3A—Fe1A—C10A—C11A−0.7 (5)C5B—Fe1B—C10B—C11B−71.1 (7)
C6A—Fe1A—C10A—C11A118.0 (6)C8B—Fe1B—C10B—C11B−158.4 (4)
C4A—Fe1A—C10A—C11A41.9 (5)C2B—Fe1B—C10B—C11B2.6 (4)
N2A—N1A—C11A—C10A−179.9 (4)N2B—N1B—C11B—C10B−171.3 (4)
C9A—C10A—C11A—N1A0.6 (8)C6B—C10B—C11B—N1B−172.7 (5)
C6A—C10A—C11A—N1A−178.5 (4)C9B—C10B—C11B—N1B15.5 (7)
Fe1A—C10A—C11A—N1A92.2 (5)Fe1B—C10B—C11B—N1B101.5 (5)
N1A—N2A—C12A—N3A−1.0 (7)N1B—N2B—C12B—N3B10.6 (7)
N1A—N2A—C12A—S1A−178.6 (3)N1B—N2B—C12B—S1B−168.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2A—H2AB···S1Ai0.862.663.370 (4)141
N3A—H3AC···S1Bii0.862.463.295 (4)165
N2B—H2BB···S1Aiii0.862.523.298 (4)151
N3B—H3BC···S1Biv0.862.473.323 (4)173
C7A—H7AA···Cg10.982.903.668 (6)136

Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, y−1, z; (iii) x, y+1, z; (iv) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2447).

References

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  • Mariño, M., Gayoso, E., Antelo, J. M., Adrio, L. A., Fernańdez, J. J. & Vila, J. M. (2006). Polyhedron, 25, 1449–1456.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2009). Acta Cryst. E65, m1524–m1525. [PMC free article] [PubMed]

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