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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m697–m698.
Published online 2010 May 22. doi:  10.1107/S1600536810018209
PMCID: PMC2979492

Ferrocene-1-carbaldehyde 4-ethyl­thio­semi­carbazone

Abstract

The asymmetric unit of title compound, [Fe(C5H5)(C9H12N3S)], contains two crystallographically independent mol­ecules, A and B. The two cyclo­penta­dienyl (Cp) rings are parallel to each other in both mol­ecules, forming dihedral angles of 2.3 (3) and 1.0 (3)°, respectively, and adopt an eclipsed conformation. The mean plane of the semicarbazone group is twisted slightly away from the attached Cp ring in both mol­ecules, the dihedral angles between the mean plane and the Cp ring being 15.3 (2) and 10.8 (2)°. The ethyl group in mol­ecule A is coplanar with the mean plane of the semicarbazone group [C—N—C—C torsion angle = −175.2 (4)°], whereas it is nearly perpendicular in mol­ecule B [C—N—C—C torsion angle = 84.8 (6)°]. In the crystal structure, inter­molecular N—H(...)S hydrogen bonds link the mol­ecules into dimers. These dimers are further linked into chains via inter­molecular C—H(...)S hydrogen bonds. The crystal studied was a non-merohedral twin with a refined ratio of the twin components of 0.265 (2):0.735 (2).

Related literature

For related structures, see: Vikneswaran et al. (2009 [triangle], 2010 [triangle]). For the preparation of the title compound, see: Casas et al. (2004 [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-66-0m697-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C9H12N3S)]
  • M r = 315.22
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m697-efi1.jpg
  • a = 7.4432 (3) Å
  • b = 10.6906 (5) Å
  • c = 18.4616 (9) Å
  • α = 77.975 (3)°
  • β = 83.807 (3)°
  • γ = 78.076 (3)°
  • V = 1402.56 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.21 mm−1
  • T = 100 K
  • 0.29 × 0.16 × 0.09 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.723, T max = 0.901
  • 8184 measured reflections
  • 8184 independent reflections
  • 6947 reflections with I > 2σ(I)

Refinement

  • R[F 2 > 2σ(F 2)] = 0.073
  • wR(F 2) = 0.170
  • S = 1.07
  • 8184 reflections
  • 362 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 3.94 e Å−3
  • Δρmin = −1.22 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 (Sheldrick, 2008 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018209/rz2450sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018209/rz2450Isup2.hkl

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

Acknowledgments

HKF thank 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 its metal complexes, herein we report the crystal structure of formylferrocene 4-ethylthiosemicarbazone.

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 its closely related structures (Vikneswaran et al., 2009, 2010). The Cp rings of each ferrocene residue are parallel, with dihedral angles of Cp1/Cp2 [C1A–C5A/C6A–C10A] = 2.3 (3)° and Cp3/Cp4 [C1B–C5B/C6B–C10B] = 1.0 (3)°. The Cp rings in both molecules adopt an eclipsed conformation [average torsion angles for C–Cg–Cg–C of 5.89 and 6.14°]. The mean plane of the semicarbazone group is slightly twisted away from the attached Cp rings in both molecules, the dihedral angles between the mean plane and the Cp ring being 15.3 (2) and 10.8 (2)° respectively. The ethyl group in molecule A is coplanar with the mean plane of semicarbazone group [torsion angle of C12A–N3A–C13A–C14B = -175.2 (4)°] whereas it is nearly perpendicular to the semicarbazone group [torsion angle of C12B–N3B–C13B–C14B = 84.8 (6)°] in molecule B.

In the crystal structure, intermolecular N2A–H2NA···S1A and N2B–H2NB···S1B hydrogen bonds link the molecules into dimers. These dimers are linked into one-dimensional chain via intermolecular C4A–H4AA···S1B hydrogen bonds (Fig. 2, Table 1).

Experimental

Formylferrocene 4-ethylthiosemicarbazone was prepared as described by Casas et al. (2004). The single crystals were grown from a CH2Cl2/n-CH6H14 (1:1 v/v) solution at room temperature in the dark.

Refinement

N bound H-atoms were located from difference Fourier map and refined freely. The rest of H-atoms were placed in calculated positions, with C–H = 0.93–0.98 Å and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). Rotating-group model were applied for methyl group. The highest residual density peak is located 0.88 Å from atom Fe1B and the deepest hole is located 1.32 Å from atom C12B. The crystal studied is a non-merohedral twin with the refined ratio of twin components of 0.265 (2):0.735 (2).

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 the molecules link into 1-D chains. Hydrogen atoms not involved in the hydrogen-bonding (dashed lines) are omitted for clarity.

Crystal data

[Fe(C5H5)(C9H12N3S)]Z = 4
Mr = 315.22F(000) = 656
Triclinic, P1Dx = 1.493 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4432 (3) ÅCell parameters from 9974 reflections
b = 10.6906 (5) Åθ = 2.3–30.0°
c = 18.4616 (9) ŵ = 1.21 mm1
α = 77.975 (3)°T = 100 K
β = 83.807 (3)°Block, brown
γ = 78.076 (3)°0.29 × 0.16 × 0.09 mm
V = 1402.56 (11) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer8184 independent reflections
Radiation source: fine-focus sealed tube6947 reflections with I > 2σ(I)
graphiteRint = 0.0000
[var phi] and ω scansθmax = 30.1°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −10→10
Tmin = 0.723, Tmax = 0.901k = −14→15
8184 measured reflectionsl = −11→25

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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0564P)2 + 6.6396P] where P = (Fo2 + 2Fc2)/3
8184 reflections(Δ/σ)max < 0.001
362 parametersΔρmax = 3.94 e Å3
0 restraintsΔρmin = −1.22 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 > 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)

xyzUiso*/Ueq
Fe1A0.13896 (8)−0.05245 (6)0.63951 (3)0.01124 (13)
S1A0.29669 (15)0.61964 (10)0.42316 (6)0.0175 (2)
N1A0.2762 (5)0.2535 (3)0.5056 (2)0.0145 (7)
N2A0.3209 (5)0.3757 (3)0.4940 (2)0.0150 (7)
N3A0.0898 (5)0.4487 (3)0.4141 (2)0.0140 (7)
C1A−0.1290 (6)0.0406 (4)0.6505 (2)0.0171 (8)
H1AA−0.20020.09850.61080.021*
C2A−0.1151 (6)−0.0966 (4)0.6707 (2)0.0174 (8)
H2AA−0.1754−0.14980.64740.021*
C3A0.0008 (6)−0.1433 (4)0.7305 (2)0.0201 (9)
H3AA0.0348−0.23430.75550.024*
C4A0.0590 (7)−0.0348 (5)0.7480 (2)0.0211 (9)
H4AA0.1403−0.03760.78690.025*
C5A−0.0221 (6)0.0788 (5)0.6976 (3)0.0203 (9)
H5AA−0.00520.16790.69590.024*
C6A0.2245 (5)−0.0166 (4)0.5289 (2)0.0137 (7)
H6AA0.14910.03320.48830.016*
C7A0.2465 (6)−0.1531 (4)0.5565 (2)0.0151 (8)
H7AA0.1878−0.21360.53840.018*
C8A0.3655 (6)−0.1867 (4)0.6163 (2)0.0168 (8)
H8AA0.4035−0.27400.64580.020*
C9A0.4196 (5)−0.0705 (4)0.6252 (2)0.0154 (8)
H9AA0.5011−0.06380.66200.018*
C10A0.3323 (5)0.0348 (4)0.5711 (2)0.0123 (7)
C11A0.3566 (5)0.1695 (4)0.5581 (2)0.0146 (8)
H11A0.43040.19470.58790.018*
C12A0.2306 (5)0.4739 (4)0.4442 (2)0.0125 (7)
C13A−0.0243 (6)0.5431 (4)0.3617 (2)0.0151 (8)
H13A0.04950.56850.31640.018*
H13B−0.07410.62030.38250.018*
C14A−0.1810 (6)0.4851 (5)0.3440 (3)0.0223 (9)
H14A−0.25220.54660.30730.033*
H14B−0.25830.46520.38830.033*
H14C−0.13140.40670.32530.033*
Fe1B0.30485 (8)0.46654 (6)0.14382 (3)0.01438 (14)
S1B0.24370 (18)−0.06556 (11)−0.06872 (7)0.0224 (2)
N1B0.2135 (5)0.2488 (4)0.0132 (2)0.0195 (8)
N2B0.1830 (6)0.1303 (4)0.0031 (2)0.0223 (8)
N3B0.4293 (6)0.1273 (4)−0.0817 (2)0.0252 (9)
C1B0.5691 (6)0.3613 (5)0.1531 (2)0.0197 (9)
H1BA0.65110.33010.11270.024*
C2B0.5528 (6)0.4837 (4)0.1738 (3)0.0189 (9)
H2BA0.62300.55160.15070.023*
C3B0.4170 (6)0.4906 (4)0.2346 (3)0.0187 (8)
H3BA0.37810.56350.26090.022*
C4B0.3493 (6)0.3726 (4)0.2500 (2)0.0190 (8)
H4BA0.25390.35020.28870.023*
C5B0.4432 (7)0.2922 (4)0.2007 (3)0.0209 (9)
H5BA0.42310.20520.19870.025*
C6B0.2535 (6)0.5058 (5)0.0337 (2)0.0195 (9)
H6BA0.34130.4832−0.00720.023*
C7B0.2245 (7)0.6241 (4)0.0616 (3)0.0221 (9)
H7BA0.28950.69670.04330.026*
C8B0.0860 (6)0.6177 (4)0.1209 (3)0.0226 (9)
H8BA0.03910.68500.15060.027*
C9B0.0287 (6)0.4950 (5)0.1302 (3)0.0205 (9)
H9BA−0.06480.46380.16720.025*
C10B0.1320 (6)0.4262 (4)0.0763 (2)0.0171 (8)
C11B0.1143 (6)0.2982 (4)0.0654 (3)0.0193 (9)
H11B0.03200.25270.09600.023*
C12B0.2896 (7)0.0721 (5)−0.0494 (3)0.0204 (9)
C13B0.5572 (7)0.0852 (5)−0.1416 (3)0.0284 (11)
H13C0.5809−0.0091−0.13400.034*
H13D0.67310.1122−0.13980.034*
C14B0.4841 (9)0.1411 (6)−0.2179 (3)0.0374 (13)
H14D0.57420.1130−0.25530.056*
H14E0.45930.2345−0.22560.056*
H14F0.37270.1109−0.22080.056*
H2NA0.416 (8)0.390 (5)0.507 (3)0.016 (13)*
H2NB0.073 (12)0.109 (8)0.015 (5)0.07 (3)*
H3NB0.458 (11)0.186 (7)−0.053 (4)0.05 (2)*
H3NA0.046 (8)0.384 (6)0.437 (3)0.026 (15)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe1A0.0099 (3)0.0130 (3)0.0111 (3)−0.0036 (2)−0.0009 (2)−0.0015 (2)
S1A0.0198 (5)0.0117 (5)0.0231 (5)−0.0066 (4)−0.0057 (4)−0.0027 (4)
N1A0.0116 (15)0.0160 (17)0.0175 (17)−0.0050 (13)−0.0004 (13)−0.0046 (13)
N2A0.0147 (16)0.0125 (16)0.0189 (17)−0.0042 (13)−0.0027 (13)−0.0028 (13)
N3A0.0161 (16)0.0100 (15)0.0162 (17)−0.0061 (13)−0.0021 (13)0.0009 (13)
C1A0.0122 (17)0.018 (2)0.020 (2)−0.0018 (15)0.0021 (15)−0.0048 (16)
C2A0.0162 (18)0.018 (2)0.021 (2)−0.0094 (15)0.0027 (16)−0.0045 (16)
C3A0.025 (2)0.018 (2)0.016 (2)−0.0071 (17)0.0021 (17)0.0007 (16)
C4A0.025 (2)0.028 (2)0.0121 (19)−0.0105 (18)0.0030 (16)−0.0041 (17)
C5A0.026 (2)0.020 (2)0.018 (2)−0.0067 (17)0.0034 (17)−0.0086 (17)
C6A0.0102 (17)0.0179 (19)0.0135 (18)−0.0039 (14)0.0000 (14)−0.0032 (15)
C7A0.0132 (17)0.0169 (19)0.0153 (19)−0.0026 (14)−0.0007 (14)−0.0037 (15)
C8A0.0136 (18)0.0140 (19)0.021 (2)0.0005 (14)−0.0020 (15)−0.0006 (15)
C9A0.0098 (16)0.018 (2)0.0181 (19)−0.0022 (14)−0.0029 (14)−0.0026 (15)
C10A0.0086 (16)0.0145 (18)0.0136 (18)−0.0033 (14)0.0015 (13)−0.0023 (14)
C11A0.0114 (17)0.0159 (19)0.0175 (19)−0.0048 (14)−0.0015 (14)−0.0031 (15)
C12A0.0135 (17)0.0125 (18)0.0133 (18)−0.0047 (14)0.0006 (14)−0.0053 (14)
C13A0.0137 (17)0.0115 (18)0.019 (2)−0.0021 (14)−0.0043 (15)−0.0001 (15)
C14A0.018 (2)0.025 (2)0.026 (2)−0.0062 (17)−0.0062 (17)−0.0051 (18)
Fe1B0.0136 (3)0.0156 (3)0.0144 (3)−0.0045 (2)−0.0029 (2)−0.0013 (2)
S1B0.0350 (6)0.0162 (5)0.0199 (5)−0.0113 (4)−0.0027 (4)−0.0051 (4)
N1B0.0208 (18)0.0182 (18)0.0225 (19)−0.0076 (14)−0.0043 (15)−0.0056 (15)
N2B0.029 (2)0.0195 (19)0.023 (2)−0.0120 (16)−0.0028 (16)−0.0053 (15)
N3B0.0226 (19)0.031 (2)0.029 (2)−0.0131 (17)−0.0025 (16)−0.0129 (18)
C1B0.019 (2)0.024 (2)0.016 (2)−0.0011 (17)−0.0039 (16)−0.0049 (17)
C2B0.0118 (18)0.021 (2)0.024 (2)−0.0075 (16)−0.0022 (15)−0.0016 (17)
C3B0.0182 (19)0.017 (2)0.023 (2)−0.0021 (16)−0.0045 (16)−0.0076 (16)
C4B0.0179 (19)0.021 (2)0.017 (2)−0.0045 (16)−0.0027 (16)−0.0009 (16)
C5B0.026 (2)0.016 (2)0.021 (2)−0.0027 (17)−0.0045 (17)−0.0033 (16)
C6B0.021 (2)0.023 (2)0.0134 (19)−0.0066 (17)−0.0042 (16)0.0020 (16)
C7B0.031 (2)0.0121 (19)0.022 (2)−0.0031 (17)−0.0130 (19)0.0039 (16)
C8B0.023 (2)0.015 (2)0.029 (2)0.0032 (17)−0.0095 (18)−0.0050 (17)
C9B0.0165 (19)0.024 (2)0.021 (2)−0.0053 (17)−0.0042 (16)−0.0028 (17)
C10B0.0169 (19)0.018 (2)0.0171 (19)−0.0042 (15)−0.0068 (15)−0.0019 (16)
C11B0.019 (2)0.022 (2)0.020 (2)−0.0095 (17)−0.0035 (16)−0.0021 (17)
C12B0.025 (2)0.020 (2)0.018 (2)−0.0074 (17)−0.0062 (17)−0.0029 (16)
C13B0.023 (2)0.030 (3)0.035 (3)−0.0052 (19)0.003 (2)−0.014 (2)
C14B0.041 (3)0.046 (3)0.033 (3)−0.018 (3)0.014 (2)−0.024 (3)

Geometric parameters (Å, °)

Fe1A—C2A2.037 (4)Fe1B—C3B2.036 (4)
Fe1A—C3A2.046 (4)Fe1B—C4B2.036 (4)
Fe1A—C1A2.046 (4)Fe1B—C2B2.037 (4)
Fe1A—C8A2.046 (4)Fe1B—C10B2.048 (4)
Fe1A—C9A2.051 (4)Fe1B—C9B2.050 (4)
Fe1A—C10A2.051 (4)Fe1B—C6B2.051 (4)
Fe1A—C5A2.052 (5)Fe1B—C7B2.053 (4)
Fe1A—C7A2.052 (4)Fe1B—C8B2.054 (4)
Fe1A—C6A2.053 (4)Fe1B—C1B2.060 (4)
Fe1A—C4A2.063 (4)Fe1B—C5B2.064 (5)
S1A—C12A1.687 (4)S1B—C12B1.691 (5)
N1A—C11A1.283 (5)N1B—C11B1.285 (6)
N1A—N2A1.383 (5)N1B—N2B1.384 (5)
N2A—C12A1.356 (5)N2B—C12B1.357 (7)
N2A—H2NA0.82 (6)N2B—H2NB0.89 (9)
N3A—C12A1.335 (5)N3B—C12B1.326 (6)
N3A—C13A1.447 (5)N3B—C13B1.461 (7)
N3A—H3NA0.84 (6)N3B—H3NB0.97 (8)
C1A—C5A1.410 (6)C1B—C2B1.417 (7)
C1A—C2A1.421 (6)C1B—C5B1.426 (6)
C1A—H1AA0.9800C1B—H1BA0.9800
C2A—C3A1.418 (6)C2B—C3B1.431 (6)
C2A—H2AA0.9800C2B—H2BA0.9800
C3A—C4A1.425 (7)C3B—C4B1.418 (6)
C3A—H3AA0.9800C3B—H3BA0.9800
C4A—C5A1.433 (7)C4B—C5B1.414 (7)
C4A—H4AA0.9800C4B—H4BA0.9800
C5A—H5AA0.9800C5B—H5BA0.9800
C6A—C7A1.424 (6)C6B—C10B1.431 (6)
C6A—C10A1.430 (5)C6B—C7B1.431 (7)
C6A—H6AA0.9800C6B—H6BA0.9800
C7A—C8A1.429 (6)C7B—C8B1.421 (7)
C7A—H7AA0.9800C7B—H7BA0.9800
C8A—C9A1.428 (6)C8B—C9B1.433 (6)
C8A—H8AA0.9800C8B—H8BA0.9800
C9A—C10A1.434 (6)C9B—C10B1.424 (7)
C9A—H9AA0.9800C9B—H9BA0.9800
C10A—C11A1.456 (6)C10B—C11B1.459 (6)
C11A—H11A0.9300C11B—H11B0.9300
C13A—C14A1.523 (6)C13B—C14B1.522 (8)
C13A—H13A0.9700C13B—H13C0.9700
C13A—H13B0.9700C13B—H13D0.9700
C14A—H14A0.9600C14B—H14D0.9600
C14A—H14B0.9600C14B—H14E0.9600
C14A—H14C0.9600C14B—H14F0.9600
C2A—Fe1A—C3A40.63 (18)C3B—Fe1B—C4B40.76 (18)
C2A—Fe1A—C1A40.72 (17)C3B—Fe1B—C2B41.13 (18)
C3A—Fe1A—C1A68.45 (18)C4B—Fe1B—C2B68.65 (18)
C2A—Fe1A—C8A123.50 (18)C3B—Fe1B—C10B162.68 (18)
C3A—Fe1A—C8A106.06 (18)C4B—Fe1B—C10B125.67 (17)
C1A—Fe1A—C8A161.08 (18)C2B—Fe1B—C10B154.96 (19)
C2A—Fe1A—C9A161.10 (17)C3B—Fe1B—C9B125.40 (19)
C3A—Fe1A—C9A124.71 (18)C4B—Fe1B—C9B108.12 (18)
C1A—Fe1A—C9A157.02 (18)C2B—Fe1B—C9B162.68 (19)
C8A—Fe1A—C9A40.79 (17)C10B—Fe1B—C9B40.67 (19)
C2A—Fe1A—C10A155.75 (17)C3B—Fe1B—C6B155.00 (18)
C3A—Fe1A—C10A162.98 (17)C4B—Fe1B—C6B162.63 (19)
C1A—Fe1A—C10A121.71 (17)C2B—Fe1B—C6B119.64 (18)
C8A—Fe1A—C10A68.66 (16)C10B—Fe1B—C6B40.86 (17)
C9A—Fe1A—C10A40.93 (16)C9B—Fe1B—C6B68.61 (18)
C2A—Fe1A—C5A68.06 (18)C3B—Fe1B—C7B120.00 (18)
C3A—Fe1A—C5A68.28 (19)C4B—Fe1B—C7B155.5 (2)
C1A—Fe1A—C5A40.26 (18)C2B—Fe1B—C7B106.91 (18)
C8A—Fe1A—C5A156.34 (18)C10B—Fe1B—C7B68.64 (18)
C9A—Fe1A—C5A122.29 (18)C9B—Fe1B—C7B68.55 (19)
C10A—Fe1A—C5A109.67 (17)C6B—Fe1B—C7B40.81 (19)
C2A—Fe1A—C7A106.16 (17)C3B—Fe1B—C8B107.44 (19)
C3A—Fe1A—C7A119.01 (18)C4B—Fe1B—C8B121.0 (2)
C1A—Fe1A—C7A124.63 (17)C2B—Fe1B—C8B125.02 (19)
C8A—Fe1A—C7A40.82 (16)C10B—Fe1B—C8B68.52 (18)
C9A—Fe1A—C7A68.53 (17)C9B—Fe1B—C8B40.87 (18)
C10A—Fe1A—C7A68.29 (16)C6B—Fe1B—C8B68.4 (2)
C5A—Fe1A—C7A162.30 (18)C7B—Fe1B—C8B40.5 (2)
C2A—Fe1A—C6A119.68 (17)C3B—Fe1B—C1B68.50 (18)
C3A—Fe1A—C6A154.10 (18)C4B—Fe1B—C1B68.19 (18)
C1A—Fe1A—C6A107.78 (17)C2B—Fe1B—C1B40.47 (18)
C8A—Fe1A—C6A68.80 (17)C10B—Fe1B—C1B120.59 (18)
C9A—Fe1A—C6A68.88 (16)C9B—Fe1B—C1B155.71 (19)
C10A—Fe1A—C6A40.79 (15)C6B—Fe1B—C1B107.35 (19)
C5A—Fe1A—C6A126.39 (18)C7B—Fe1B—C1B125.0 (2)
C7A—Fe1A—C6A40.58 (16)C8B—Fe1B—C1B161.93 (19)
C2A—Fe1A—C4A68.27 (18)C3B—Fe1B—C5B68.25 (18)
C3A—Fe1A—C4A40.57 (18)C4B—Fe1B—C5B40.33 (19)
C1A—Fe1A—C4A68.32 (19)C2B—Fe1B—C5B68.20 (18)
C8A—Fe1A—C4A120.07 (19)C10B—Fe1B—C5B108.19 (18)
C9A—Fe1A—C4A108.26 (18)C9B—Fe1B—C5B121.11 (19)
C10A—Fe1A—C4A126.87 (18)C6B—Fe1B—C5B125.56 (19)
C5A—Fe1A—C4A40.75 (19)C7B—Fe1B—C5B162.4 (2)
C7A—Fe1A—C4A154.51 (18)C8B—Fe1B—C5B156.1 (2)
C6A—Fe1A—C4A163.95 (18)C1B—Fe1B—C5B40.47 (18)
C11A—N1A—N2A115.2 (3)C11B—N1B—N2B116.6 (4)
C12A—N2A—N1A119.4 (3)C12B—N2B—N1B118.6 (4)
C12A—N2A—H2NA115 (4)C12B—N2B—H2NB116 (5)
N1A—N2A—H2NA124 (4)N1B—N2B—H2NB121 (6)
C12A—N3A—C13A124.1 (3)C12B—N3B—C13B126.0 (4)
C12A—N3A—H3NA116 (4)C12B—N3B—H3NB111 (5)
C13A—N3A—H3NA117 (4)C13B—N3B—H3NB121 (5)
C5A—C1A—C2A107.9 (4)C2B—C1B—C5B107.9 (4)
C5A—C1A—Fe1A70.1 (3)C2B—C1B—Fe1B68.9 (2)
C2A—C1A—Fe1A69.3 (2)C5B—C1B—Fe1B69.9 (3)
C5A—C1A—H1AA126.1C2B—C1B—H1BA126.0
C2A—C1A—H1AA126.1C5B—C1B—H1BA126.0
Fe1A—C1A—H1AA126.1Fe1B—C1B—H1BA126.0
C3A—C2A—C1A108.3 (4)C1B—C2B—C3B108.1 (4)
C3A—C2A—Fe1A70.0 (2)C1B—C2B—Fe1B70.6 (2)
C1A—C2A—Fe1A70.0 (2)C3B—C2B—Fe1B69.4 (2)
C3A—C2A—H2AA125.8C1B—C2B—H2BA126.0
C1A—C2A—H2AA125.8C3B—C2B—H2BA126.0
Fe1A—C2A—H2AA125.8Fe1B—C2B—H2BA126.0
C2A—C3A—C4A108.1 (4)C4B—C3B—C2B107.5 (4)
C2A—C3A—Fe1A69.4 (2)C4B—C3B—Fe1B69.6 (2)
C4A—C3A—Fe1A70.4 (2)C2B—C3B—Fe1B69.5 (2)
C2A—C3A—H3AA125.9C4B—C3B—H3BA126.3
C4A—C3A—H3AA125.9C2B—C3B—H3BA126.3
Fe1A—C3A—H3AA125.9Fe1B—C3B—H3BA126.3
C3A—C4A—C5A107.2 (4)C5B—C4B—C3B108.6 (4)
C3A—C4A—Fe1A69.1 (3)C5B—C4B—Fe1B70.9 (3)
C5A—C4A—Fe1A69.2 (3)C3B—C4B—Fe1B69.6 (3)
C3A—C4A—H4AA126.4C5B—C4B—H4BA125.7
C5A—C4A—H4AA126.4C3B—C4B—H4BA125.7
Fe1A—C4A—H4AA126.4Fe1B—C4B—H4BA125.7
C1A—C5A—C4A108.5 (4)C4B—C5B—C1B107.9 (4)
C1A—C5A—Fe1A69.6 (3)C4B—C5B—Fe1B68.8 (3)
C4A—C5A—Fe1A70.0 (3)C1B—C5B—Fe1B69.6 (3)
C1A—C5A—H5AA125.8C4B—C5B—H5BA126.1
C4A—C5A—H5AA125.8C1B—C5B—H5BA126.1
Fe1A—C5A—H5AA125.8Fe1B—C5B—H5BA126.1
C7A—C6A—C10A107.6 (3)C10B—C6B—C7B107.8 (4)
C7A—C6A—Fe1A69.7 (2)C10B—C6B—Fe1B69.5 (2)
C10A—C6A—Fe1A69.5 (2)C7B—C6B—Fe1B69.7 (2)
C7A—C6A—H6AA126.2C10B—C6B—H6BA126.1
C10A—C6A—H6AA126.2C7B—C6B—H6BA126.1
Fe1A—C6A—H6AA126.2Fe1B—C6B—H6BA126.1
C6A—C7A—C8A108.5 (4)C8B—C7B—C6B108.1 (4)
C6A—C7A—Fe1A69.7 (2)C8B—C7B—Fe1B69.8 (3)
C8A—C7A—Fe1A69.4 (3)C6B—C7B—Fe1B69.5 (2)
C6A—C7A—H7AA125.7C8B—C7B—H7BA126.0
C8A—C7A—H7AA125.7C6B—C7B—H7BA126.0
Fe1A—C7A—H7AA125.7Fe1B—C7B—H7BA126.0
C9A—C8A—C7A107.9 (4)C7B—C8B—C9B108.1 (4)
C9A—C8A—Fe1A69.8 (2)C7B—C8B—Fe1B69.7 (3)
C7A—C8A—Fe1A69.8 (2)C9B—C8B—Fe1B69.4 (3)
C9A—C8A—H8AA126.0C7B—C8B—H8BA125.9
C7A—C8A—H8AA126.0C9B—C8B—H8BA125.9
Fe1A—C8A—H8AA126.0Fe1B—C8B—H8BA125.9
C8A—C9A—C10A107.7 (3)C10B—C9B—C8B107.9 (4)
C8A—C9A—Fe1A69.4 (2)C10B—C9B—Fe1B69.6 (2)
C10A—C9A—Fe1A69.6 (2)C8B—C9B—Fe1B69.7 (2)
C8A—C9A—H9AA126.1C10B—C9B—H9BA126.1
C10A—C9A—H9AA126.1C8B—C9B—H9BA126.1
Fe1A—C9A—H9AA126.1Fe1B—C9B—H9BA126.1
C6A—C10A—C9A108.2 (4)C9B—C10B—C6B108.1 (4)
C6A—C10A—C11A125.5 (4)C9B—C10B—C11B126.0 (4)
C9A—C10A—C11A126.2 (4)C6B—C10B—C11B125.9 (4)
C6A—C10A—Fe1A69.7 (2)C9B—C10B—Fe1B69.8 (2)
C9A—C10A—Fe1A69.5 (2)C6B—C10B—Fe1B69.7 (2)
C11A—C10A—Fe1A129.0 (3)C11B—C10B—Fe1B127.2 (3)
N1A—C11A—C10A120.0 (4)N1B—C11B—C10B119.4 (4)
N1A—C11A—H11A120.0N1B—C11B—H11B120.3
C10A—C11A—H11A120.0C10B—C11B—H11B120.3
N3A—C12A—N2A116.8 (4)N3B—C12B—N2B116.3 (4)
N3A—C12A—S1A123.0 (3)N3B—C12B—S1B123.8 (4)
N2A—C12A—S1A120.1 (3)N2B—C12B—S1B119.9 (4)
N3A—C13A—C14A110.0 (3)N3B—C13B—C14B112.6 (4)
N3A—C13A—H13A109.7N3B—C13B—H13C109.1
C14A—C13A—H13A109.7C14B—C13B—H13C109.1
N3A—C13A—H13B109.7N3B—C13B—H13D109.1
C14A—C13A—H13B109.7C14B—C13B—H13D109.1
H13A—C13A—H13B108.2H13C—C13B—H13D107.8
C13A—C14A—H14A109.5C13B—C14B—H14D109.5
C13A—C14A—H14B109.5C13B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
C13A—C14A—H14C109.5C13B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
C11A—N1A—N2A—C12A−174.2 (4)C11B—N1B—N2B—C12B−177.4 (4)
C2A—Fe1A—C1A—C5A119.1 (4)C3B—Fe1B—C1B—C2B−38.2 (3)
C3A—Fe1A—C1A—C5A81.4 (3)C4B—Fe1B—C1B—C2B−82.2 (3)
C8A—Fe1A—C1A—C5A157.8 (5)C10B—Fe1B—C1B—C2B158.2 (3)
C9A—Fe1A—C1A—C5A−48.1 (6)C9B—Fe1B—C1B—C2B−168.1 (4)
C10A—Fe1A—C1A—C5A−83.3 (3)C6B—Fe1B—C1B—C2B115.6 (3)
C7A—Fe1A—C1A—C5A−167.4 (3)C7B—Fe1B—C1B—C2B74.1 (3)
C6A—Fe1A—C1A—C5A−125.8 (3)C8B—Fe1B—C1B—C2B42.1 (7)
C4A—Fe1A—C1A—C5A37.6 (3)C5B—Fe1B—C1B—C2B−119.5 (4)
C3A—Fe1A—C1A—C2A−37.6 (3)C3B—Fe1B—C1B—C5B81.3 (3)
C8A—Fe1A—C1A—C2A38.8 (6)C4B—Fe1B—C1B—C5B37.3 (3)
C9A—Fe1A—C1A—C2A−167.2 (4)C2B—Fe1B—C1B—C5B119.5 (4)
C10A—Fe1A—C1A—C2A157.7 (3)C10B—Fe1B—C1B—C5B−82.3 (3)
C5A—Fe1A—C1A—C2A−119.1 (4)C9B—Fe1B—C1B—C5B−48.6 (5)
C7A—Fe1A—C1A—C2A73.5 (3)C6B—Fe1B—C1B—C5B−124.9 (3)
C6A—Fe1A—C1A—C2A115.1 (3)C7B—Fe1B—C1B—C5B−166.4 (3)
C4A—Fe1A—C1A—C2A−81.4 (3)C8B—Fe1B—C1B—C5B161.6 (6)
C5A—C1A—C2A—C3A0.0 (5)C5B—C1B—C2B—C3B0.3 (5)
Fe1A—C1A—C2A—C3A59.7 (3)Fe1B—C1B—C2B—C3B59.5 (3)
C5A—C1A—C2A—Fe1A−59.7 (3)C5B—C1B—C2B—Fe1B−59.3 (3)
C1A—Fe1A—C2A—C3A−119.3 (4)C3B—Fe1B—C2B—C1B118.9 (4)
C8A—Fe1A—C2A—C3A74.8 (3)C4B—Fe1B—C2B—C1B81.0 (3)
C9A—Fe1A—C2A—C3A45.2 (7)C10B—Fe1B—C2B—C1B−49.0 (5)
C10A—Fe1A—C2A—C3A−171.2 (4)C9B—Fe1B—C2B—C1B163.4 (6)
C5A—Fe1A—C2A—C3A−81.8 (3)C6B—Fe1B—C2B—C1B−82.1 (3)
C7A—Fe1A—C2A—C3A116.0 (3)C7B—Fe1B—C2B—C1B−124.6 (3)
C6A—Fe1A—C2A—C3A157.8 (3)C8B—Fe1B—C2B—C1B−165.3 (3)
C4A—Fe1A—C2A—C3A−37.7 (3)C5B—Fe1B—C2B—C1B37.5 (3)
C3A—Fe1A—C2A—C1A119.3 (4)C4B—Fe1B—C2B—C3B−37.9 (3)
C8A—Fe1A—C2A—C1A−165.9 (3)C10B—Fe1B—C2B—C3B−167.9 (4)
C9A—Fe1A—C2A—C1A164.5 (5)C9B—Fe1B—C2B—C3B44.5 (7)
C10A—Fe1A—C2A—C1A−51.9 (5)C6B—Fe1B—C2B—C3B159.0 (3)
C5A—Fe1A—C2A—C1A37.5 (3)C7B—Fe1B—C2B—C3B116.5 (3)
C7A—Fe1A—C2A—C1A−124.8 (3)C8B—Fe1B—C2B—C3B75.8 (3)
C6A—Fe1A—C2A—C1A−82.9 (3)C1B—Fe1B—C2B—C3B−118.9 (4)
C4A—Fe1A—C2A—C1A81.6 (3)C5B—Fe1B—C2B—C3B−81.4 (3)
C1A—C2A—C3A—C4A0.3 (5)C1B—C2B—C3B—C4B−0.8 (5)
Fe1A—C2A—C3A—C4A60.0 (3)Fe1B—C2B—C3B—C4B59.5 (3)
C1A—C2A—C3A—Fe1A−59.7 (3)C1B—C2B—C3B—Fe1B−60.3 (3)
C1A—Fe1A—C3A—C2A37.7 (3)C2B—Fe1B—C3B—C4B−118.7 (4)
C8A—Fe1A—C3A—C2A−123.1 (3)C10B—Fe1B—C3B—C4B43.9 (7)
C9A—Fe1A—C3A—C2A−163.8 (3)C9B—Fe1B—C3B—C4B76.1 (3)
C10A—Fe1A—C3A—C2A167.6 (5)C6B—Fe1B—C3B—C4B−166.2 (4)
C5A—Fe1A—C3A—C2A81.2 (3)C7B—Fe1B—C3B—C4B159.9 (3)
C7A—Fe1A—C3A—C2A−80.9 (3)C8B—Fe1B—C3B—C4B117.6 (3)
C6A—Fe1A—C3A—C2A−48.7 (5)C1B—Fe1B—C3B—C4B−81.1 (3)
C4A—Fe1A—C3A—C2A119.1 (4)C5B—Fe1B—C3B—C4B−37.4 (3)
C2A—Fe1A—C3A—C4A−119.1 (4)C4B—Fe1B—C3B—C2B118.7 (4)
C1A—Fe1A—C3A—C4A−81.4 (3)C10B—Fe1B—C3B—C2B162.7 (5)
C8A—Fe1A—C3A—C4A117.7 (3)C9B—Fe1B—C3B—C2B−165.2 (3)
C9A—Fe1A—C3A—C4A77.1 (3)C6B—Fe1B—C3B—C2B−47.4 (5)
C10A—Fe1A—C3A—C4A48.4 (7)C7B—Fe1B—C3B—C2B−81.4 (3)
C5A—Fe1A—C3A—C4A−37.9 (3)C8B—Fe1B—C3B—C2B−123.7 (3)
C7A—Fe1A—C3A—C4A159.9 (3)C1B—Fe1B—C3B—C2B37.6 (3)
C6A—Fe1A—C3A—C4A−167.9 (4)C5B—Fe1B—C3B—C2B81.3 (3)
C2A—C3A—C4A—C5A−0.4 (5)C2B—C3B—C4B—C5B1.0 (5)
Fe1A—C3A—C4A—C5A58.9 (3)Fe1B—C3B—C4B—C5B60.4 (3)
C2A—C3A—C4A—Fe1A−59.3 (3)C2B—C3B—C4B—Fe1B−59.4 (3)
C2A—Fe1A—C4A—C3A37.8 (3)C3B—Fe1B—C4B—C5B−119.3 (4)
C1A—Fe1A—C4A—C3A81.7 (3)C2B—Fe1B—C4B—C5B−81.0 (3)
C8A—Fe1A—C4A—C3A−79.4 (3)C10B—Fe1B—C4B—C5B75.4 (3)
C9A—Fe1A—C4A—C3A−122.4 (3)C9B—Fe1B—C4B—C5B117.0 (3)
C10A—Fe1A—C4A—C3A−164.1 (3)C6B—Fe1B—C4B—C5B40.9 (7)
C5A—Fe1A—C4A—C3A118.9 (4)C7B—Fe1B—C4B—C5B−165.1 (4)
C7A—Fe1A—C4A—C3A−44.2 (5)C8B—Fe1B—C4B—C5B160.0 (3)
C6A—Fe1A—C4A—C3A160.6 (5)C1B—Fe1B—C4B—C5B−37.4 (3)
C2A—Fe1A—C4A—C5A−81.2 (3)C2B—Fe1B—C4B—C3B38.3 (3)
C3A—Fe1A—C4A—C5A−118.9 (4)C10B—Fe1B—C4B—C3B−165.3 (3)
C1A—Fe1A—C4A—C5A−37.2 (3)C9B—Fe1B—C4B—C3B−123.6 (3)
C8A—Fe1A—C4A—C5A161.7 (3)C6B—Fe1B—C4B—C3B160.2 (6)
C9A—Fe1A—C4A—C5A118.6 (3)C7B—Fe1B—C4B—C3B−45.7 (6)
C10A—Fe1A—C4A—C5A77.0 (3)C8B—Fe1B—C4B—C3B−80.7 (3)
C7A—Fe1A—C4A—C5A−163.1 (4)C1B—Fe1B—C4B—C3B81.9 (3)
C6A—Fe1A—C4A—C5A41.7 (7)C5B—Fe1B—C4B—C3B119.3 (4)
C2A—C1A—C5A—C4A−0.2 (5)C3B—C4B—C5B—C1B−0.8 (5)
Fe1A—C1A—C5A—C4A−59.5 (3)Fe1B—C4B—C5B—C1B58.8 (3)
C2A—C1A—C5A—Fe1A59.2 (3)C3B—C4B—C5B—Fe1B−59.6 (3)
C3A—C4A—C5A—C1A0.4 (5)C2B—C1B—C5B—C4B0.3 (5)
Fe1A—C4A—C5A—C1A59.2 (3)Fe1B—C1B—C5B—C4B−58.3 (3)
C3A—C4A—C5A—Fe1A−58.8 (3)C2B—C1B—C5B—Fe1B58.6 (3)
C2A—Fe1A—C5A—C1A−37.9 (3)C3B—Fe1B—C5B—C4B37.8 (3)
C3A—Fe1A—C5A—C1A−81.9 (3)C2B—Fe1B—C5B—C4B82.3 (3)
C8A—Fe1A—C5A—C1A−162.2 (4)C10B—Fe1B—C5B—C4B−124.1 (3)
C9A—Fe1A—C5A—C1A159.9 (3)C9B—Fe1B—C5B—C4B−81.4 (3)
C10A—Fe1A—C5A—C1A116.2 (3)C6B—Fe1B—C5B—C4B−166.1 (3)
C7A—Fe1A—C5A—C1A36.1 (7)C7B—Fe1B—C5B—C4B159.3 (5)
C6A—Fe1A—C5A—C1A73.5 (3)C8B—Fe1B—C5B—C4B−46.3 (6)
C4A—Fe1A—C5A—C1A−119.7 (4)C1B—Fe1B—C5B—C4B119.7 (4)
C2A—Fe1A—C5A—C4A81.7 (3)C3B—Fe1B—C5B—C1B−81.9 (3)
C3A—Fe1A—C5A—C4A37.8 (3)C4B—Fe1B—C5B—C1B−119.7 (4)
C1A—Fe1A—C5A—C4A119.7 (4)C2B—Fe1B—C5B—C1B−37.5 (3)
C8A—Fe1A—C5A—C4A−42.6 (5)C10B—Fe1B—C5B—C1B116.1 (3)
C9A—Fe1A—C5A—C4A−80.5 (3)C9B—Fe1B—C5B—C1B158.9 (3)
C10A—Fe1A—C5A—C4A−124.1 (3)C6B—Fe1B—C5B—C1B74.2 (3)
C7A—Fe1A—C5A—C4A155.7 (5)C7B—Fe1B—C5B—C1B39.5 (7)
C6A—Fe1A—C5A—C4A−166.8 (2)C8B—Fe1B—C5B—C1B−166.0 (4)
C2A—Fe1A—C6A—C7A−80.0 (3)C3B—Fe1B—C6B—C10B−166.8 (4)
C3A—Fe1A—C6A—C7A−45.8 (5)C4B—Fe1B—C6B—C10B44.7 (7)
C1A—Fe1A—C6A—C7A−122.9 (2)C2B—Fe1B—C6B—C10B159.3 (3)
C8A—Fe1A—C6A—C7A37.4 (2)C9B—Fe1B—C6B—C10B−37.6 (3)
C9A—Fe1A—C6A—C7A81.3 (3)C7B—Fe1B—C6B—C10B−119.1 (4)
C10A—Fe1A—C6A—C7A118.9 (3)C8B—Fe1B—C6B—C10B−81.7 (3)
C5A—Fe1A—C6A—C7A−163.5 (2)C1B—Fe1B—C6B—C10B117.0 (3)
C4A—Fe1A—C6A—C7A163.9 (6)C5B—Fe1B—C6B—C10B76.1 (3)
C2A—Fe1A—C6A—C10A161.1 (2)C3B—Fe1B—C6B—C7B−47.7 (6)
C3A—Fe1A—C6A—C10A−164.6 (4)C4B—Fe1B—C6B—C7B163.9 (6)
C1A—Fe1A—C6A—C10A118.3 (2)C2B—Fe1B—C6B—C7B−81.6 (3)
C8A—Fe1A—C6A—C10A−81.5 (3)C10B—Fe1B—C6B—C7B119.1 (4)
C9A—Fe1A—C6A—C10A−37.6 (2)C9B—Fe1B—C6B—C7B81.5 (3)
C5A—Fe1A—C6A—C10A77.6 (3)C8B—Fe1B—C6B—C7B37.5 (3)
C7A—Fe1A—C6A—C10A−118.9 (3)C1B—Fe1B—C6B—C7B−123.9 (3)
C4A—Fe1A—C6A—C10A45.0 (7)C5B—Fe1B—C6B—C7B−164.8 (3)
C10A—C6A—C7A—C8A0.7 (5)C10B—C6B—C7B—C8B−0.1 (5)
Fe1A—C6A—C7A—C8A−58.7 (3)Fe1B—C6B—C7B—C8B−59.4 (3)
C10A—C6A—C7A—Fe1A59.4 (3)C10B—C6B—C7B—Fe1B59.2 (3)
C2A—Fe1A—C7A—C6A117.0 (2)C3B—Fe1B—C7B—C8B−81.8 (3)
C3A—Fe1A—C7A—C6A159.0 (2)C4B—Fe1B—C7B—C8B−49.1 (5)
C1A—Fe1A—C7A—C6A76.4 (3)C2B—Fe1B—C7B—C8B−124.6 (3)
C8A—Fe1A—C7A—C6A−120.1 (3)C10B—Fe1B—C7B—C8B81.5 (3)
C9A—Fe1A—C7A—C6A−82.2 (2)C9B—Fe1B—C7B—C8B37.7 (3)
C10A—Fe1A—C7A—C6A−38.0 (2)C6B—Fe1B—C7B—C8B119.4 (4)
C5A—Fe1A—C7A—C6A48.8 (6)C1B—Fe1B—C7B—C8B−165.3 (3)
C4A—Fe1A—C7A—C6A−169.7 (4)C5B—Fe1B—C7B—C8B164.4 (6)
C2A—Fe1A—C7A—C8A−122.9 (3)C3B—Fe1B—C7B—C6B158.8 (3)
C3A—Fe1A—C7A—C8A−80.9 (3)C4B—Fe1B—C7B—C6B−168.5 (4)
C1A—Fe1A—C7A—C8A−163.6 (2)C2B—Fe1B—C7B—C6B116.0 (3)
C9A—Fe1A—C7A—C8A37.9 (2)C10B—Fe1B—C7B—C6B−37.9 (3)
C10A—Fe1A—C7A—C8A82.1 (3)C9B—Fe1B—C7B—C6B−81.7 (3)
C5A—Fe1A—C7A—C8A168.9 (5)C8B—Fe1B—C7B—C6B−119.4 (4)
C6A—Fe1A—C7A—C8A120.1 (3)C1B—Fe1B—C7B—C6B75.3 (3)
C4A—Fe1A—C7A—C8A−49.7 (5)C5B—Fe1B—C7B—C6B45.0 (7)
C6A—C7A—C8A—C9A−0.7 (5)C6B—C7B—C8B—C9B0.2 (5)
Fe1A—C7A—C8A—C9A−59.6 (3)Fe1B—C7B—C8B—C9B−59.0 (3)
C6A—C7A—C8A—Fe1A58.9 (3)C6B—C7B—C8B—Fe1B59.2 (3)
C2A—Fe1A—C8A—C9A−165.8 (2)C3B—Fe1B—C8B—C7B116.0 (3)
C3A—Fe1A—C8A—C9A−125.0 (3)C4B—Fe1B—C8B—C7B158.5 (3)
C1A—Fe1A—C8A—C9A164.8 (5)C2B—Fe1B—C8B—C7B74.1 (3)
C10A—Fe1A—C8A—C9A37.9 (2)C10B—Fe1B—C8B—C7B−81.8 (3)
C5A—Fe1A—C8A—C9A−52.6 (5)C9B—Fe1B—C8B—C7B−119.6 (4)
C7A—Fe1A—C8A—C9A119.0 (4)C6B—Fe1B—C8B—C7B−37.8 (3)
C6A—Fe1A—C8A—C9A81.8 (3)C1B—Fe1B—C8B—C7B42.0 (7)
C4A—Fe1A—C8A—C9A−83.3 (3)C5B—Fe1B—C8B—C7B−168.4 (4)
C2A—Fe1A—C8A—C7A75.2 (3)C3B—Fe1B—C8B—C9B−124.4 (3)
C3A—Fe1A—C8A—C7A116.0 (3)C4B—Fe1B—C8B—C9B−81.9 (3)
C1A—Fe1A—C8A—C7A45.9 (6)C2B—Fe1B—C8B—C9B−166.3 (3)
C9A—Fe1A—C8A—C7A−119.0 (4)C10B—Fe1B—C8B—C9B37.7 (3)
C10A—Fe1A—C8A—C7A−81.1 (3)C6B—Fe1B—C8B—C9B81.8 (3)
C5A—Fe1A—C8A—C7A−171.6 (4)C7B—Fe1B—C8B—C9B119.6 (4)
C6A—Fe1A—C8A—C7A−37.2 (2)C1B—Fe1B—C8B—C9B161.6 (5)
C4A—Fe1A—C8A—C7A157.7 (2)C5B—Fe1B—C8B—C9B−48.9 (6)
C7A—C8A—C9A—C10A0.4 (5)C7B—C8B—C9B—C10B−0.2 (5)
Fe1A—C8A—C9A—C10A−59.2 (3)Fe1B—C8B—C9B—C10B−59.3 (3)
C7A—C8A—C9A—Fe1A59.6 (3)C7B—C8B—C9B—Fe1B59.2 (3)
C2A—Fe1A—C9A—C8A39.1 (6)C3B—Fe1B—C9B—C10B−165.9 (3)
C3A—Fe1A—C9A—C8A73.3 (3)C4B—Fe1B—C9B—C10B−124.1 (3)
C1A—Fe1A—C9A—C8A−167.5 (4)C2B—Fe1B—C9B—C10B159.6 (6)
C10A—Fe1A—C9A—C8A−119.1 (4)C6B—Fe1B—C9B—C10B37.8 (3)
C5A—Fe1A—C9A—C8A157.8 (3)C7B—Fe1B—C9B—C10B81.8 (3)
C7A—Fe1A—C9A—C8A−37.9 (2)C8B—Fe1B—C9B—C10B119.1 (4)
C6A—Fe1A—C9A—C8A−81.6 (3)C1B—Fe1B—C9B—C10B−47.1 (5)
C4A—Fe1A—C9A—C8A115.2 (3)C5B—Fe1B—C9B—C10B−81.8 (3)
C2A—Fe1A—C9A—C10A158.2 (5)C3B—Fe1B—C9B—C8B75.0 (3)
C3A—Fe1A—C9A—C10A−167.6 (3)C4B—Fe1B—C9B—C8B116.8 (3)
C1A—Fe1A—C9A—C10A−48.4 (5)C2B—Fe1B—C9B—C8B40.5 (7)
C8A—Fe1A—C9A—C10A119.1 (4)C10B—Fe1B—C9B—C8B−119.1 (4)
C5A—Fe1A—C9A—C10A−83.1 (3)C6B—Fe1B—C9B—C8B−81.3 (3)
C7A—Fe1A—C9A—C10A81.2 (3)C7B—Fe1B—C9B—C8B−37.4 (3)
C6A—Fe1A—C9A—C10A37.5 (2)C1B—Fe1B—C9B—C8B−166.2 (4)
C4A—Fe1A—C9A—C10A−125.7 (3)C5B—Fe1B—C9B—C8B159.1 (3)
C7A—C6A—C10A—C9A−0.5 (5)C8B—C9B—C10B—C6B0.1 (5)
Fe1A—C6A—C10A—C9A59.0 (3)Fe1B—C9B—C10B—C6B−59.3 (3)
C7A—C6A—C10A—C11A176.4 (4)C8B—C9B—C10B—C11B−178.7 (4)
Fe1A—C6A—C10A—C11A−124.1 (4)Fe1B—C9B—C10B—C11B121.9 (4)
C7A—C6A—C10A—Fe1A−59.5 (3)C8B—C9B—C10B—Fe1B59.4 (3)
C8A—C9A—C10A—C6A0.1 (5)C7B—C6B—C10B—C9B0.0 (5)
Fe1A—C9A—C10A—C6A−59.1 (3)Fe1B—C6B—C10B—C9B59.4 (3)
C8A—C9A—C10A—C11A−176.8 (4)C7B—C6B—C10B—C11B178.8 (4)
Fe1A—C9A—C10A—C11A124.0 (4)Fe1B—C6B—C10B—C11B−121.8 (4)
C8A—C9A—C10A—Fe1A59.2 (3)C7B—C6B—C10B—Fe1B−59.3 (3)
C2A—Fe1A—C10A—C6A−43.3 (5)C3B—Fe1B—C10B—C9B41.8 (7)
C3A—Fe1A—C10A—C6A156.7 (6)C4B—Fe1B—C10B—C9B75.6 (3)
C1A—Fe1A—C10A—C6A−80.4 (3)C2B—Fe1B—C10B—C9B−165.8 (4)
C8A—Fe1A—C10A—C6A81.9 (3)C6B—Fe1B—C10B—C9B−119.3 (4)
C9A—Fe1A—C10A—C6A119.6 (3)C7B—Fe1B—C10B—C9B−81.5 (3)
C5A—Fe1A—C10A—C6A−123.4 (3)C8B—Fe1B—C10B—C9B−37.9 (3)
C7A—Fe1A—C10A—C6A37.8 (2)C1B—Fe1B—C10B—C9B159.5 (3)
C4A—Fe1A—C10A—C6A−165.8 (3)C5B—Fe1B—C10B—C9B116.9 (3)
C2A—Fe1A—C10A—C9A−162.9 (4)C3B—Fe1B—C10B—C6B161.1 (6)
C3A—Fe1A—C10A—C9A37.0 (7)C4B—Fe1B—C10B—C6B−165.0 (3)
C1A—Fe1A—C10A—C9A159.9 (3)C2B—Fe1B—C10B—C6B−46.5 (5)
C8A—Fe1A—C10A—C9A−37.8 (3)C9B—Fe1B—C10B—C6B119.3 (4)
C5A—Fe1A—C10A—C9A117.0 (3)C7B—Fe1B—C10B—C6B37.8 (3)
C7A—Fe1A—C10A—C9A−81.8 (3)C8B—Fe1B—C10B—C6B81.4 (3)
C6A—Fe1A—C10A—C9A−119.6 (3)C1B—Fe1B—C10B—C6B−81.2 (3)
C4A—Fe1A—C10A—C9A74.5 (3)C5B—Fe1B—C10B—C6B−123.8 (3)
C2A—Fe1A—C10A—C11A76.5 (6)C3B—Fe1B—C10B—C11B−78.6 (8)
C3A—Fe1A—C10A—C11A−83.5 (7)C4B—Fe1B—C10B—C11B−44.8 (5)
C1A—Fe1A—C10A—C11A39.4 (4)C2B—Fe1B—C10B—C11B73.8 (6)
C8A—Fe1A—C10A—C11A−158.3 (4)C9B—Fe1B—C10B—C11B−120.4 (5)
C9A—Fe1A—C10A—C11A−120.5 (5)C6B—Fe1B—C10B—C11B120.3 (5)
C5A—Fe1A—C10A—C11A−3.5 (4)C7B—Fe1B—C10B—C11B158.1 (5)
C7A—Fe1A—C10A—C11A157.6 (4)C8B—Fe1B—C10B—C11B−158.3 (5)
C6A—Fe1A—C10A—C11A119.8 (5)C1B—Fe1B—C10B—C11B39.1 (5)
C4A—Fe1A—C10A—C11A−46.0 (4)C5B—Fe1B—C10B—C11B−3.5 (5)
N2A—N1A—C11A—C10A−174.7 (4)N2B—N1B—C11B—C10B−176.5 (4)
C6A—C10A—C11A—N1A0.7 (6)C9B—C10B—C11B—N1B178.3 (4)
C9A—C10A—C11A—N1A177.0 (4)C6B—C10B—C11B—N1B−0.3 (7)
Fe1A—C10A—C11A—N1A−91.0 (5)Fe1B—C10B—C11B—N1B−91.0 (5)
C13A—N3A—C12A—N2A178.3 (4)C13B—N3B—C12B—N2B−177.3 (5)
C13A—N3A—C12A—S1A−1.4 (6)C13B—N3B—C12B—S1B4.3 (7)
N1A—N2A—C12A—N3A6.2 (6)N1B—N2B—C12B—N3B7.1 (6)
N1A—N2A—C12A—S1A−174.1 (3)N1B—N2B—C12B—S1B−174.4 (3)
C12A—N3A—C13A—C14A−175.2 (4)C12B—N3B—C13B—C14B84.8 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2A—H2NA···S1Ai0.82 (6)2.59 (6)3.387 (4)164 (5)
N2B—H2NB···S1Bii0.89 (9)2.55 (9)3.430 (5)170 (5)
C4A—H4AA···S1Biii0.982.793.715 (4)157

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2450).

References

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  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
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  • Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2009). Acta Cryst. E65, m1524–m1525. [PMC free article] [PubMed]
  • Vikneswaran, M. R., Teoh, S. G., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, m679. [PMC free article] [PubMed]

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