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Acta Cryst. (2009). E65, m1027    [ doi:10.1107/S1600536809030086 ]

Bis(ferrocenecarbaldehyde 4-methylthiosemicarbazonato-[kappa]2N1,S)zinc(II) methanol solvate

M. R. Vikneswaran, S. G. Teoh, C. K. Quah and H.-K. Fun

Abstract top

In the title compound, [Fe2Zn(C5H5)2(C8H9N3S)2]·CH3OH, the dihedral angles between the substituted and unsubstituted cyclopentadienyl rings are 89.34 (8) and 85.73 (9)°, respectively. The two Zn/S/C/N/N five-membered rings adopt envelope conformations, with the ZnII atom at the flap. Each methanol solvent molecule is linked to three ferrocene groups via intermolecular O-H...N, N-H...O and C-H...O hydrogen bonds. The crystal structure is further consolidated by C-H...[pi] interactions.

Comment top

As a continuation of our research related to ferrocenyl thiosemicarbazones and its metal complexes, herein we report the synthesis and crystal structure of a ZnII complex formed with formylferrocene 4-methylthiosemicarbazone.

The Fe—C distances (Fig. 1) are as expected for a ferrocene derivative, and are comparable to those observed in closely related structures (Seiler & Dunitz, 1979; Vikneswaran et al., 2009). In the ferrocene groups, the Fe1···Cg1/Cg2 and Fe2···Cg3/Cg4 distances are 1.6514 (7)/1.6453 (6) Å, and 1.6564 (6)/1.6497 (6) Å, respectively, and the Cg···Fe···Cg angle is 178.75 (3) and 175.27 (3)°, respectively for Fe1 and Fe2 atoms, where Cg1, Cg3 and Cg2, Cg4 are the centroids of the unsubstituted [Cp1 (C1—C5) and Cp3 (C11—C15)] and substituted [Cp2 (C6—C10) and Cp4 (C16—C20)] Cp rings, respectively. The dihedral angle between the substituted Cp rings is 89.34 (8)° [the value for the unsubstituted Cp rings = 85.73 (9)°] indicating that the two ferrocene groups position themselves almost perpendicular to each other. Each of the Cp1/Cp2 and Cp3/Cp4 pairs are approximately parallel [dihedral angle for Cp1/Cp2 = 2.05 (8) and for Cp3/Cp4 = 5.73 (8)°] and each ring is essentially planar [maximum deviation for Cp1 is 0.002 (2) Å for atom C2; for Cp2 is 0.007 (1) Å for atom C9; for Cp3 is 0.002 (1) Å for atoms C12, C13 and C14; and for Cp4 is 0.010 (1) Å for atom C16].

The angles around the Zn1 atom ranges from 86.60 (3) to 132.032 (14)°, forming a distorted tetrahedral environment. The two five-membered rings, Zn1/S1/C22/N2/N1 (A) and Zn1/S2/C25/N4/N3 (B), adopt envelope conformations with the Zn atom at the flap; the puckering parameters (Cremer & Pople, 1975) are Q = 0.1507 (8) Å and Θ = 187.6 (5)° for ring A, and Q = 0.1111 (8) Å and Θ = 177.9 (6)° for ring B. In the solid state (Fig 2), each methanol molecule is linked to three ferrocene molecules via intermolecular O1—H1···N4, N5—H2···O1 and C18—H18A···O1 hydrogen bonds. The crystal structure is further consolidated by C—H···π interactions (Table 1).

Related literature top

For related structures, see: Vikneswaran et al. (2009); Seiler & Dunitz (1979). For the preparation, see: Mariño et al. (2006). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1, Cg3, Cg4 and Cg5 are the centroids of the C1–C5, C11–C15, C16–C20 and Zn1/S1/C22/N2/N1 rings, respectively.

Experimental top

Formylferrocene 4-methylthiosemicarbazone was prepared as described by Mariño et al. (2006). Zn(CH3COO)2.2H2O (0.21 g, 1 mmol) dissolved in methanol (60 ml) was added dropwise at room temperature to a mixture of formylferrocene 4-methylthiosemicarbazone (0.30 g, 1 mmol) and KOH (0.12 g, 2 mmol) in absolute methanol (15 ml). Amorphous orange solids separated out immediately. The suspension was stirred under reflux for 4 h and filtered. After several days, brown crystals were obtained from the filtrate.

Refinement top

N-bound and O-bound H atoms were located in a difference Fourier map and refined as riding with the parent atom with an isotropic thermal parameter 1.2 and 1.5 times, respectively, that of the parent atom. All other 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 1.5 Ueq(C). A rotating-group model was applied for the methyl groups. The maximum and minimum residual electron density peaks of 1.63 and -0.33 eÅ-3, respectively, were located at 0.80 Å and 0.36 Å from the Fe2 and H27B atoms, respectively.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. Part of the crystal packing of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
Bis(ferrocenecarbaldehyde 4-methylthiosemicarbazonato-κ2N1,S)zinc(II) methanol solvate top
Crystal data top
[Fe2Zn(C5H5)2(C8H9N3S)2]·CH4OF(000) = 1432
Mr = 697.78Dx = 1.624 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9581 reflections
a = 10.9490 (1) Åθ = 2.3–39.8°
b = 9.4365 (1) ŵ = 2.02 mm−1
c = 28.1899 (3) ÅT = 100 K
β = 101.448 (1)°Block, brown
V = 2854.64 (5) Å30.36 × 0.21 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		14925 independent reflections
Radiation source: fine-focus sealed tube11613 reflections with I > 2σ(I)
graphiteRint = 0.036
φ and ω scansθmax = 37.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −18→18
Tmin = 0.532, Tmax = 0.752k = −15→15
66919 measured reflectionsl = −48→48
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0372P)2 + 1.1076P]
where P = (Fo2 + 2Fc2)/3
14925 reflections(Δ/σ)max = 0.004
355 parametersΔρmax = 1.63 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
[Fe2Zn(C5H5)2(C8H9N3S)2]·CH4OV = 2854.64 (5) Å3
Mr = 697.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.9490 (1) ŵ = 2.02 mm−1
b = 9.4365 (1) ÅT = 100 K
c = 28.1899 (3) Å0.36 × 0.21 × 0.15 mm
β = 101.448 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		14925 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		11613 reflections with I > 2σ(I)
Tmin = 0.532, Tmax = 0.752Rint = 0.036
66919 measured reflectionsθmax = 37.5°
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.085Δρmax = 1.63 e Å−3
S = 1.03Δρmin = −0.33 e Å−3
14925 reflectionsAbsolute structure: ?
355 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 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) top
xyzUiso*/Ueq
Zn10.466846 (13)0.874062 (18)0.913577 (5)0.01586 (3)
Fe10.306836 (16)0.86548 (2)0.704222 (6)0.01419 (4)
Fe20.985568 (15)0.80244 (2)0.880148 (6)0.01416 (4)
S10.41083 (3)1.08484 (4)0.941830 (12)0.02241 (7)
S20.39805 (3)0.64888 (4)0.920651 (13)0.02035 (6)
N10.43015 (9)0.96457 (12)0.84659 (4)0.01548 (18)
N20.36985 (9)1.09421 (13)0.84119 (4)0.01673 (19)
N30.64175 (9)0.79164 (12)0.92541 (4)0.01518 (18)
N40.65645 (9)0.65047 (12)0.93923 (4)0.01542 (18)
N50.29437 (11)1.27509 (14)0.88056 (5)0.0223 (2)
H20.28011.30940.90660.027*
N60.55829 (10)0.44289 (13)0.94845 (4)0.0196 (2)
H30.49500.39750.94940.024*
C10.13526 (12)0.80316 (16)0.71554 (5)0.0201 (2)
H1A0.08360.85430.73450.024*
C20.13267 (13)0.82038 (16)0.66519 (5)0.0221 (2)
H2A0.07870.88550.64340.027*
C30.22260 (14)0.72664 (17)0.65208 (5)0.0247 (3)
H3A0.24120.71600.61970.030*
C40.28126 (13)0.65217 (16)0.69439 (6)0.0232 (3)
H4A0.34720.58090.69620.028*
C50.22705 (12)0.69916 (15)0.73344 (5)0.0206 (2)
H5A0.24960.66630.76700.025*
C60.34723 (11)1.06143 (14)0.73498 (5)0.0173 (2)
H6A0.29161.11980.75020.021*
C70.35675 (12)1.06461 (15)0.68519 (5)0.0195 (2)
H7A0.30791.12510.66010.023*
C80.44765 (12)0.96267 (16)0.67786 (5)0.0203 (2)
H8A0.47200.94150.64700.024*
C90.49386 (11)0.89433 (16)0.72265 (5)0.0184 (2)
H9A0.55690.81930.72830.022*
C100.43300 (11)0.95626 (14)0.75871 (4)0.0159 (2)
C110.98425 (12)0.94343 (15)0.82424 (5)0.0207 (2)
H11A0.96891.04560.82520.025*
C121.10230 (12)0.87512 (16)0.83719 (5)0.0213 (2)
H12A1.18260.92230.84840.026*
C131.08336 (12)0.72681 (16)0.83113 (5)0.0212 (2)
H13A1.14830.65390.83730.025*
C140.95335 (13)0.70258 (16)0.81409 (5)0.0204 (2)
H14A0.91320.61020.80670.024*
C150.89247 (12)0.83665 (16)0.81002 (5)0.0196 (2)
H15A0.80270.85250.79970.024*
C160.97126 (11)0.91423 (16)0.94052 (5)0.0199 (2)
H16A0.96371.01740.94270.024*
C171.08492 (11)0.83541 (18)0.94877 (5)0.0226 (3)
H17A1.16910.87520.95730.027*
C181.05450 (12)0.68873 (17)0.94153 (5)0.0216 (3)
H18A1.11450.61070.94400.026*
C190.92240 (11)0.67500 (15)0.92959 (5)0.0176 (2)
H19A0.87580.58630.92240.021*
C200.86960 (10)0.81478 (15)0.92949 (4)0.0160 (2)
C210.45564 (11)0.90477 (15)0.80830 (4)0.0162 (2)
H21A0.49380.81650.81330.019*
C220.35672 (11)1.15094 (15)0.88276 (5)0.0176 (2)
C230.22804 (14)1.33448 (18)0.83546 (6)0.0261 (3)
H23A0.17531.41020.84210.039*
H23B0.17801.26220.81700.039*
H23C0.28681.37050.81730.039*
C240.74080 (11)0.86180 (14)0.92128 (4)0.0160 (2)
H24A0.72750.95580.91170.019*
C250.54956 (11)0.58180 (15)0.93734 (4)0.0157 (2)
C260.67565 (13)0.36712 (16)0.95984 (5)0.0230 (3)
H26A0.65980.26730.96120.035*
H26B0.72190.39850.99060.035*
H26C0.72300.38540.93530.035*
O10.19264 (10)0.36504 (11)0.96199 (4)0.02148 (19)
H10.23550.35920.98910.032*
C270.09851 (15)0.2593 (2)0.95292 (6)0.0336 (4)
H27A0.02930.28770.96700.050*
H27B0.13150.17130.96700.050*
H27C0.07110.24750.91860.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01284 (5)0.01938 (8)0.01524 (6)0.00138 (5)0.00252 (4)0.00098 (6)
Fe10.01512 (7)0.01382 (8)0.01383 (7)−0.00051 (6)0.00337 (5)0.00039 (6)
Fe20.01090 (6)0.01444 (8)0.01707 (7)−0.00035 (6)0.00264 (5)−0.00001 (7)
S10.02330 (14)0.02456 (17)0.01853 (13)0.00411 (13)0.00209 (11)−0.00436 (13)
S20.01366 (11)0.02284 (16)0.02418 (14)−0.00291 (11)0.00286 (10)0.00307 (13)
N10.0129 (4)0.0166 (5)0.0169 (4)0.0012 (3)0.0028 (3)0.0007 (4)
N20.0150 (4)0.0153 (5)0.0200 (4)0.0017 (4)0.0035 (3)−0.0002 (4)
N30.0141 (4)0.0158 (5)0.0155 (4)−0.0006 (3)0.0028 (3)−0.0001 (4)
N40.0148 (4)0.0153 (5)0.0159 (4)−0.0008 (3)0.0026 (3)0.0005 (4)
N50.0239 (5)0.0182 (5)0.0257 (5)0.0036 (4)0.0071 (4)−0.0025 (5)
N60.0200 (4)0.0181 (5)0.0201 (5)−0.0036 (4)0.0022 (4)0.0025 (4)
C10.0173 (5)0.0193 (6)0.0243 (6)−0.0025 (4)0.0051 (4)−0.0018 (5)
C20.0222 (5)0.0199 (6)0.0214 (6)−0.0040 (5)−0.0029 (4)−0.0001 (5)
C30.0336 (7)0.0205 (7)0.0210 (6)−0.0072 (6)0.0078 (5)−0.0057 (5)
C40.0243 (6)0.0148 (6)0.0316 (7)−0.0007 (5)0.0083 (5)−0.0011 (5)
C50.0221 (5)0.0179 (6)0.0218 (5)−0.0038 (5)0.0045 (4)0.0031 (5)
C60.0186 (5)0.0140 (5)0.0182 (5)−0.0007 (4)0.0009 (4)0.0008 (4)
C70.0214 (5)0.0175 (6)0.0186 (5)−0.0037 (4)0.0015 (4)0.0037 (5)
C80.0202 (5)0.0244 (7)0.0171 (5)−0.0037 (5)0.0056 (4)0.0024 (5)
C90.0151 (4)0.0231 (6)0.0175 (5)0.0003 (4)0.0046 (4)0.0013 (5)
C100.0157 (4)0.0165 (6)0.0153 (5)−0.0003 (4)0.0022 (4)0.0005 (4)
C110.0216 (5)0.0151 (6)0.0260 (6)0.0005 (4)0.0064 (5)0.0038 (5)
C120.0169 (5)0.0224 (7)0.0264 (6)−0.0022 (5)0.0088 (4)0.0028 (5)
C130.0216 (5)0.0193 (6)0.0249 (6)0.0040 (5)0.0099 (5)0.0019 (5)
C140.0249 (5)0.0173 (6)0.0193 (5)−0.0020 (5)0.0053 (4)−0.0014 (5)
C150.0187 (5)0.0206 (6)0.0188 (5)0.0009 (4)0.0022 (4)0.0025 (5)
C160.0161 (4)0.0216 (6)0.0215 (5)−0.0030 (4)0.0028 (4)−0.0047 (5)
C170.0137 (4)0.0316 (8)0.0211 (5)−0.0009 (5)0.0003 (4)−0.0034 (6)
C180.0160 (5)0.0277 (7)0.0205 (5)0.0047 (5)0.0019 (4)0.0043 (5)
C190.0160 (4)0.0181 (6)0.0190 (5)0.0015 (4)0.0039 (4)0.0027 (5)
C200.0127 (4)0.0179 (6)0.0174 (5)−0.0001 (4)0.0031 (4)−0.0006 (4)
C210.0148 (4)0.0168 (6)0.0166 (5)0.0020 (4)0.0022 (4)0.0019 (4)
C220.0144 (4)0.0161 (6)0.0222 (5)−0.0002 (4)0.0034 (4)−0.0016 (5)
C230.0231 (6)0.0235 (7)0.0328 (7)0.0071 (5)0.0081 (5)0.0038 (6)
C240.0141 (4)0.0159 (5)0.0182 (5)0.0005 (4)0.0038 (4)0.0007 (4)
C250.0159 (4)0.0182 (6)0.0126 (4)−0.0020 (4)0.0022 (4)0.0001 (4)
C260.0259 (6)0.0178 (6)0.0243 (6)0.0013 (5)0.0027 (5)−0.0004 (5)
O10.0251 (4)0.0193 (5)0.0188 (4)−0.0008 (4)0.0013 (3)−0.0008 (4)
C270.0280 (6)0.0505 (11)0.0207 (6)−0.0146 (7)0.0007 (5)−0.0007 (7)
Geometric parameters (Å, °) top
Zn1—N32.0322 (10)C4—H4A0.98
Zn1—N12.0385 (11)C5—H5A0.98
Zn1—S12.2716 (4)C6—C71.4284 (18)
Zn1—S22.2764 (4)C6—C101.4369 (18)
Fe1—C12.0529 (13)C6—H6A0.98
Fe1—C22.0482 (13)C7—C81.428 (2)
Fe1—C32.0468 (15)C7—H7A0.98
Fe1—C42.0436 (15)C8—C91.4186 (19)
Fe1—C52.0470 (14)C8—H8A0.98
Fe1—C62.0529 (14)C9—C101.4449 (17)
Fe1—C72.0577 (14)C9—H9A0.98
Fe1—C82.0556 (13)C10—C211.4540 (17)
Fe1—C92.0286 (12)C11—C151.423 (2)
Fe1—C102.0394 (13)C11—C121.4256 (19)
Fe2—C112.0603 (14)C11—H11A0.98
Fe2—C122.0457 (13)C12—C131.420 (2)
Fe2—C132.0377 (13)C12—H12A0.98
Fe2—C142.0542 (14)C13—C141.4276 (19)
Fe2—C152.0618 (13)C13—H13A0.98
Fe2—C162.0347 (14)C14—C151.424 (2)
Fe2—C172.0462 (14)C14—H14A0.98
Fe2—C182.0486 (14)C15—H15A0.98
Fe2—C192.0614 (13)C16—C171.4286 (19)
Fe2—C202.0645 (12)C16—C201.4419 (18)
S1—C221.7668 (14)C16—H16A0.98
S2—C251.7504 (13)C17—C181.429 (2)
N1—C211.2965 (16)C17—H17A0.98
N1—N21.3841 (16)C18—C191.4244 (18)
N2—C221.3219 (17)C18—H18A0.98
N3—C241.2954 (16)C19—C201.4399 (19)
N3—N41.3883 (16)C19—H19A0.98
N4—C251.3296 (16)C20—C241.4524 (16)
N5—C221.3511 (18)C21—H21A0.93
N5—C231.446 (2)C23—H23A0.96
N5—H20.84C23—H23B0.96
N6—C251.3467 (18)C23—H23C0.96
N6—C261.4497 (18)C24—H24A0.93
N6—H30.82C26—H26A0.96
C1—C21.423 (2)C26—H26B0.96
C1—C51.423 (2)C26—H26C0.96
C1—H1A0.98O1—C271.421 (2)
C2—C31.426 (2)O1—H10.82
C2—H2A0.98C27—H27A0.96
C3—C41.423 (2)C27—H27B0.96
C3—H3A0.98C27—H27C0.96
C4—C51.421 (2)
N3—Zn1—N1108.57 (4)C3—C4—Fe169.77 (9)
N3—Zn1—S1126.07 (3)C5—C4—H4A126.1
N1—Zn1—S186.60 (3)C3—C4—H4A126.1
N3—Zn1—S286.89 (3)Fe1—C4—H4A126.1
N1—Zn1—S2117.67 (3)C4—C5—C1108.33 (12)
S1—Zn1—S2132.032 (14)C4—C5—Fe169.54 (8)
C9—Fe1—C1041.61 (5)C1—C5—Fe169.91 (8)
C9—Fe1—C4105.73 (6)C4—C5—H5A125.8
C10—Fe1—C4124.75 (6)C1—C5—H5A125.8
C9—Fe1—C3123.91 (6)Fe1—C5—H5A125.8
C10—Fe1—C3162.00 (6)C7—C6—C10107.67 (11)
C4—Fe1—C340.72 (6)C7—C6—Fe169.85 (8)
C9—Fe1—C5119.31 (6)C10—C6—Fe168.94 (8)
C10—Fe1—C5107.36 (5)C7—C6—H6A126.2
C4—Fe1—C540.66 (6)C10—C6—H6A126.2
C3—Fe1—C568.33 (6)Fe1—C6—H6A126.2
C9—Fe1—C2161.87 (6)C8—C7—C6108.46 (12)
C10—Fe1—C2155.66 (6)C8—C7—Fe169.60 (8)
C4—Fe1—C268.57 (6)C6—C7—Fe169.49 (8)
C3—Fe1—C240.75 (6)C8—C7—H7A125.8
C5—Fe1—C268.33 (6)C6—C7—H7A125.8
C9—Fe1—C1155.09 (5)Fe1—C7—H7A125.8
C10—Fe1—C1120.48 (5)C9—C8—C7108.25 (11)
C4—Fe1—C168.53 (6)C9—C8—Fe168.66 (7)
C3—Fe1—C168.43 (6)C7—C8—Fe169.76 (7)
C5—Fe1—C140.63 (6)C9—C8—H8A125.9
C2—Fe1—C140.61 (6)C7—C8—H8A125.9
C9—Fe1—C669.45 (5)Fe1—C8—H8A125.9
C10—Fe1—C641.11 (5)C8—C9—C10108.02 (12)
C4—Fe1—C6163.08 (6)C8—C9—Fe170.70 (7)
C3—Fe1—C6155.29 (6)C10—C9—Fe169.60 (7)
C5—Fe1—C6126.44 (5)C8—C9—H9A126.0
C2—Fe1—C6120.91 (6)C10—C9—H9A126.0
C1—Fe1—C6108.63 (5)Fe1—C9—H9A126.0
C9—Fe1—C840.64 (5)C6—C10—C9107.57 (11)
C10—Fe1—C868.92 (5)C6—C10—C21130.49 (11)
C4—Fe1—C8118.88 (6)C9—C10—C21121.79 (12)
C3—Fe1—C8106.82 (6)C6—C10—Fe169.95 (7)
C5—Fe1—C8153.92 (6)C9—C10—Fe168.79 (7)
C2—Fe1—C8125.71 (6)C21—C10—Fe1122.99 (9)
C1—Fe1—C8163.57 (6)C15—C11—C12107.79 (13)
C6—Fe1—C868.69 (5)C15—C11—Fe269.86 (8)
C9—Fe1—C768.74 (6)C12—C11—Fe269.14 (8)
C10—Fe1—C768.75 (5)C15—C11—H11A126.1
C4—Fe1—C7154.22 (6)C12—C11—H11A126.1
C3—Fe1—C7120.16 (6)Fe2—C11—H11A126.1
C5—Fe1—C7164.10 (6)C13—C12—C11108.15 (12)
C2—Fe1—C7108.47 (6)C13—C12—Fe269.35 (7)
C1—Fe1—C7126.92 (6)C11—C12—Fe270.24 (7)
C6—Fe1—C740.67 (5)C13—C12—H12A125.9
C8—Fe1—C740.64 (6)C11—C12—H12A125.9
C16—Fe2—C13152.48 (6)Fe2—C12—H12A125.9
C16—Fe2—C12118.83 (6)C12—C13—C14108.08 (12)
C13—Fe2—C1240.70 (6)C12—C13—Fe269.95 (8)
C16—Fe2—C1740.98 (5)C14—C13—Fe270.20 (7)
C13—Fe2—C17116.23 (6)C12—C13—H13A126.0
C12—Fe2—C17103.37 (6)C14—C13—H13A126.0
C16—Fe2—C1869.00 (6)Fe2—C13—H13A126.0
C13—Fe2—C18103.54 (6)C15—C14—C13107.72 (12)
C12—Fe2—C18120.46 (5)C15—C14—Fe270.05 (8)
C17—Fe2—C1840.85 (6)C13—C14—Fe268.96 (8)
C16—Fe2—C14165.53 (5)C15—C14—H14A126.1
C13—Fe2—C1440.83 (6)C13—C14—H14A126.1
C12—Fe2—C1468.42 (6)Fe2—C14—H14A126.1
C17—Fe2—C14152.90 (6)C11—C15—C14108.26 (11)
C18—Fe2—C14119.58 (6)C11—C15—Fe269.74 (8)
C16—Fe2—C11108.36 (6)C14—C15—Fe269.47 (8)
C13—Fe2—C1168.43 (6)C11—C15—H15A125.9
C12—Fe2—C1140.63 (5)C14—C15—H15A125.9
C17—Fe2—C11123.14 (6)Fe2—C15—H15A125.9
C18—Fe2—C11158.40 (6)C17—C16—C20107.85 (13)
C14—Fe2—C1168.22 (6)C17—C16—Fe269.94 (8)
C16—Fe2—C1969.21 (6)C20—C16—Fe270.52 (7)
C13—Fe2—C19123.10 (6)C17—C16—H16A126.1
C12—Fe2—C19158.23 (5)C20—C16—H16A126.1
C17—Fe2—C1968.67 (6)Fe2—C16—H16A126.1
C18—Fe2—C1940.55 (5)C16—C17—C18108.08 (11)
C14—Fe2—C19108.97 (6)C16—C17—Fe269.08 (7)
C11—Fe2—C19160.30 (5)C18—C17—Fe269.67 (8)
C16—Fe2—C15127.98 (6)C16—C17—H17A126.0
C13—Fe2—C1568.35 (5)C18—C17—H17A126.0
C12—Fe2—C1568.16 (5)Fe2—C17—H17A126.0
C17—Fe2—C15162.08 (7)C19—C18—C17108.59 (12)
C18—Fe2—C15157.07 (6)C19—C18—Fe270.21 (8)
C14—Fe2—C1540.48 (6)C17—C18—Fe269.49 (8)
C11—Fe2—C1540.40 (6)C19—C18—H18A125.7
C19—Fe2—C15124.83 (5)C17—C18—H18A125.7
C16—Fe2—C2041.18 (5)Fe2—C18—H18A125.7
C13—Fe2—C20162.34 (6)C18—C19—C20107.80 (12)
C12—Fe2—C20156.94 (6)C18—C19—Fe269.24 (8)
C17—Fe2—C2068.72 (5)C20—C19—Fe269.69 (7)
C18—Fe2—C2068.48 (5)C18—C19—H19A126.1
C14—Fe2—C20128.23 (5)C20—C19—H19A126.1
C11—Fe2—C20124.55 (5)Fe2—C19—H19A126.1
C19—Fe2—C2040.85 (5)C19—C20—C16107.66 (11)
C15—Fe2—C20112.58 (5)C19—C20—C24131.07 (12)
C22—S1—Zn192.41 (5)C16—C20—C24121.27 (12)
C25—S2—Zn192.79 (5)C19—C20—Fe269.46 (7)
C21—N1—N2118.03 (11)C16—C20—Fe268.30 (7)
C21—N1—Zn1123.60 (9)C24—C20—Fe2128.13 (9)
N2—N1—Zn1118.31 (8)N1—C21—C10129.13 (12)
C22—N2—N1113.19 (11)N1—C21—H21A115.4
C24—N3—N4117.59 (10)C10—C21—H21A115.4
C24—N3—Zn1124.62 (9)N2—C22—N5116.96 (12)
N4—N3—Zn1117.79 (7)N2—C22—S1128.13 (10)
C25—N4—N3113.85 (10)N5—C22—S1114.91 (10)
C22—N5—C23122.50 (13)N5—C23—H23A109.5
C22—N5—H2118.1N5—C23—H23B109.5
C23—N5—H2117.9H23A—C23—H23B109.5
C25—N6—C26123.40 (11)N5—C23—H23C109.5
C25—N6—H3119.7H23A—C23—H23C109.5
C26—N6—H3116.9H23B—C23—H23C109.5
C2—C1—C5107.77 (12)N3—C24—C20129.29 (13)
C2—C1—Fe169.52 (7)N3—C24—H24A115.4
C5—C1—Fe169.46 (7)C20—C24—H24A115.4
C2—C1—H1A126.1N4—C25—N6116.34 (11)
C5—C1—H1A126.1N4—C25—S2127.90 (11)
Fe1—C1—H1A126.1N6—C25—S2115.74 (9)
C1—C2—C3108.03 (13)N6—C26—H26A109.5
C1—C2—Fe169.87 (7)N6—C26—H26B109.5
C3—C2—Fe169.57 (8)H26A—C26—H26B109.5
C1—C2—H2A126.0N6—C26—H26C109.5
C3—C2—H2A126.0H26A—C26—H26C109.5
Fe1—C2—H2A126.0H26B—C26—H26C109.5
C4—C3—C2108.01 (12)C27—O1—H1112.5
C4—C3—Fe169.52 (8)O1—C27—H27A109.5
C2—C3—Fe169.68 (8)O1—C27—H27B109.5
C4—C3—H3A126.0H27A—C27—H27B109.5
C2—C3—H3A126.0O1—C27—H27C109.5
Fe1—C3—H3A126.0H27A—C27—H27C109.5
C5—C4—C3107.86 (13)H27B—C27—H27C109.5
C5—C4—Fe169.80 (8)
N3—Zn1—S1—C22119.19 (6)C16—Fe2—C11—C15−127.61 (8)
N1—Zn1—S1—C228.62 (5)C13—Fe2—C11—C1581.51 (9)
S2—Zn1—S1—C22−116.32 (4)C12—Fe2—C11—C15119.22 (12)
N3—Zn1—S2—C256.07 (5)C17—Fe2—C11—C15−170.46 (8)
N1—Zn1—S2—C25115.44 (5)C18—Fe2—C11—C15153.17 (15)
S1—Zn1—S2—C25−132.08 (4)C14—Fe2—C11—C1537.41 (8)
N3—Zn1—N1—C2145.06 (11)C19—Fe2—C11—C15−48.1 (2)
S1—Zn1—N1—C21172.09 (10)C20—Fe2—C11—C15−84.86 (9)
S2—Zn1—N1—C21−51.35 (10)C16—Fe2—C11—C12113.17 (9)
N3—Zn1—N1—N2−137.85 (8)C13—Fe2—C11—C12−37.71 (9)
S1—Zn1—N1—N2−10.82 (8)C17—Fe2—C11—C1270.32 (10)
S2—Zn1—N1—N2125.75 (8)C18—Fe2—C11—C1234.0 (2)
C21—N1—N2—C22−175.16 (11)C14—Fe2—C11—C12−81.80 (9)
Zn1—N1—N2—C227.58 (13)C19—Fe2—C11—C12−167.33 (15)
N1—Zn1—N3—C2453.54 (11)C15—Fe2—C11—C12−119.22 (12)
S1—Zn1—N3—C24−46.08 (11)C20—Fe2—C11—C12155.93 (8)
S2—Zn1—N3—C24171.74 (10)C15—C11—C12—C13−0.19 (15)
N1—Zn1—N3—N4−126.95 (8)Fe2—C11—C12—C1359.19 (9)
S1—Zn1—N3—N4133.42 (7)C15—C11—C12—Fe2−59.38 (9)
S2—Zn1—N3—N4−8.76 (8)C16—Fe2—C12—C13155.84 (8)
C24—N3—N4—C25−172.80 (11)C17—Fe2—C12—C13114.85 (9)
Zn1—N3—N4—C257.66 (13)C18—Fe2—C12—C1374.51 (10)
C9—Fe1—C1—C2−162.75 (13)C14—Fe2—C12—C13−38.02 (8)
C10—Fe1—C1—C2159.67 (8)C11—Fe2—C12—C13−119.29 (12)
C4—Fe1—C1—C2−81.69 (10)C19—Fe2—C12—C1349.22 (19)
C3—Fe1—C1—C2−37.77 (9)C15—Fe2—C12—C13−81.74 (9)
C5—Fe1—C1—C2−119.19 (12)C20—Fe2—C12—C13−178.34 (12)
C6—Fe1—C1—C2116.07 (9)C16—Fe2—C12—C11−84.88 (10)
C8—Fe1—C1—C238.3 (2)C13—Fe2—C12—C11119.29 (12)
C7—Fe1—C1—C274.48 (10)C17—Fe2—C12—C11−125.86 (9)
C9—Fe1—C1—C5−43.56 (17)C18—Fe2—C12—C11−166.20 (9)
C10—Fe1—C1—C5−81.13 (9)C14—Fe2—C12—C1181.27 (9)
C4—Fe1—C1—C537.50 (9)C19—Fe2—C12—C11168.51 (14)
C3—Fe1—C1—C581.42 (9)C15—Fe2—C12—C1137.55 (9)
C2—Fe1—C1—C5119.19 (12)C20—Fe2—C12—C11−59.05 (17)
C6—Fe1—C1—C5−124.73 (8)C11—C12—C13—C140.36 (16)
C8—Fe1—C1—C5157.54 (19)Fe2—C12—C13—C1460.10 (9)
C7—Fe1—C1—C5−166.32 (8)C11—C12—C13—Fe2−59.74 (9)
C5—C1—C2—C30.18 (16)C16—Fe2—C13—C12−50.89 (16)
Fe1—C1—C2—C359.32 (10)C17—Fe2—C13—C12−79.78 (10)
C5—C1—C2—Fe1−59.14 (9)C18—Fe2—C13—C12−121.30 (9)
C9—Fe1—C2—C1156.35 (18)C14—Fe2—C13—C12118.85 (12)
C10—Fe1—C2—C1−46.58 (17)C11—Fe2—C13—C1237.64 (8)
C4—Fe1—C2—C181.58 (9)C19—Fe2—C13—C12−160.41 (8)
C3—Fe1—C2—C1119.23 (12)C15—Fe2—C13—C1281.24 (9)
C5—Fe1—C2—C137.72 (9)C20—Fe2—C13—C12177.86 (15)
C6—Fe1—C2—C1−82.76 (10)C16—Fe2—C13—C14−169.74 (12)
C8—Fe1—C2—C1−167.52 (9)C12—Fe2—C13—C14−118.85 (12)
C7—Fe1—C2—C1−125.69 (9)C17—Fe2—C13—C14161.37 (9)
C9—Fe1—C2—C337.1 (2)C18—Fe2—C13—C14119.85 (9)
C10—Fe1—C2—C3−165.81 (12)C11—Fe2—C13—C14−81.21 (9)
C4—Fe1—C2—C3−37.64 (9)C19—Fe2—C13—C1480.74 (10)
C5—Fe1—C2—C3−81.51 (9)C15—Fe2—C13—C14−37.61 (8)
C1—Fe1—C2—C3−119.23 (12)C20—Fe2—C13—C1459.0 (2)
C6—Fe1—C2—C3158.01 (8)C12—C13—C14—C15−0.39 (15)
C8—Fe1—C2—C373.25 (11)Fe2—C13—C14—C1559.55 (9)
C7—Fe1—C2—C3115.08 (9)C12—C13—C14—Fe2−59.95 (10)
C1—C2—C3—C4−0.35 (16)C16—Fe2—C14—C1541.7 (3)
Fe1—C2—C3—C459.15 (10)C13—Fe2—C14—C15−119.11 (12)
C1—C2—C3—Fe1−59.5 (1)C12—Fe2—C14—C15−81.22 (8)
C9—Fe1—C3—C473.72 (10)C17—Fe2—C14—C15−158.10 (12)
C10—Fe1—C3—C441.6 (2)C18—Fe2—C14—C15165.07 (7)
C5—Fe1—C3—C4−37.85 (8)C11—Fe2—C14—C15−37.34 (8)
C2—Fe1—C3—C4−119.36 (12)C19—Fe2—C14—C15121.85 (8)
C1—Fe1—C3—C4−81.71 (9)C20—Fe2—C14—C1580.22 (10)
C6—Fe1—C3—C4−169.58 (11)C16—Fe2—C14—C13160.8 (2)
C8—Fe1—C3—C4114.97 (9)C12—Fe2—C14—C1337.90 (8)
C7—Fe1—C3—C4157.13 (8)C17—Fe2—C14—C13−38.98 (16)
C9—Fe1—C3—C2−166.92 (8)C18—Fe2—C14—C13−75.82 (9)
C10—Fe1—C3—C2160.91 (15)C11—Fe2—C14—C1381.77 (9)
C4—Fe1—C3—C2119.36 (12)C19—Fe2—C14—C13−119.04 (8)
C5—Fe1—C3—C281.51 (9)C15—Fe2—C14—C13119.11 (12)
C1—Fe1—C3—C237.65 (9)C20—Fe2—C14—C13−160.67 (8)
C6—Fe1—C3—C2−50.22 (16)C12—C11—C15—C14−0.06 (15)
C8—Fe1—C3—C2−125.68 (9)Fe2—C11—C15—C14−58.98 (9)
C7—Fe1—C3—C2−83.51 (9)C12—C11—C15—Fe258.93 (9)
C2—C3—C4—C50.39 (16)C13—C14—C15—C110.28 (15)
Fe1—C3—C4—C559.64 (10)Fe2—C14—C15—C1159.15 (9)
C2—C3—C4—Fe1−59.25 (10)C13—C14—C15—Fe2−58.87 (9)
C9—Fe1—C4—C5116.91 (8)C16—Fe2—C15—C1172.51 (9)
C10—Fe1—C4—C575.50 (9)C13—Fe2—C15—C11−81.73 (8)
C3—Fe1—C4—C5−118.94 (12)C12—Fe2—C15—C11−37.75 (8)
C2—Fe1—C4—C5−81.26 (9)C17—Fe2—C15—C1126.8 (2)
C1—Fe1—C4—C5−37.48 (8)C18—Fe2—C15—C11−154.77 (12)
C6—Fe1—C4—C546.0 (2)C14—Fe2—C15—C11−119.65 (11)
C8—Fe1—C4—C5158.76 (8)C19—Fe2—C15—C11162.20 (8)
C7—Fe1—C4—C5−169.53 (11)C20—Fe2—C15—C11117.32 (8)
C9—Fe1—C4—C3−124.14 (8)C16—Fe2—C15—C14−167.84 (8)
C10—Fe1—C4—C3−165.56 (8)C13—Fe2—C15—C1437.92 (8)
C5—Fe1—C4—C3118.94 (12)C12—Fe2—C15—C1481.90 (8)
C2—Fe1—C4—C337.68 (8)C17—Fe2—C15—C14146.47 (16)
C1—Fe1—C4—C381.46 (9)C18—Fe2—C15—C14−35.11 (16)
C6—Fe1—C4—C3164.94 (16)C11—Fe2—C15—C14119.65 (11)
C8—Fe1—C4—C3−82.29 (9)C19—Fe2—C15—C14−78.15 (9)
C7—Fe1—C4—C3−50.58 (16)C20—Fe2—C15—C14−123.03 (8)
C3—C4—C5—C1−0.28 (16)C13—Fe2—C16—C17−41.36 (17)
Fe1—C4—C5—C159.34 (10)C12—Fe2—C16—C17−76.64 (10)
C3—C4—C5—Fe1−59.62 (10)C18—Fe2—C16—C1737.47 (9)
C2—C1—C5—C40.06 (16)C14—Fe2—C16—C17166.4 (2)
Fe1—C1—C5—C4−59.11 (10)C11—Fe2—C16—C17−119.75 (9)
C2—C1—C5—Fe159.17 (9)C19—Fe2—C16—C1781.02 (9)
C9—Fe1—C5—C4−79.84 (10)C15—Fe2—C16—C17−160.39 (9)
C10—Fe1—C5—C4−123.55 (9)C20—Fe2—C16—C17118.38 (12)
C3—Fe1—C5—C437.90 (9)C13—Fe2—C16—C20−159.73 (11)
C2—Fe1—C5—C481.90 (9)C12—Fe2—C16—C20164.98 (8)
C1—Fe1—C5—C4119.60 (12)C17—Fe2—C16—C20−118.38 (12)
C6—Fe1—C5—C4−164.92 (8)C18—Fe2—C16—C20−80.91 (8)
C8—Fe1—C5—C4−46.17 (16)C14—Fe2—C16—C2048.0 (3)
C7—Fe1—C5—C4163.23 (18)C11—Fe2—C16—C20121.88 (8)
C9—Fe1—C5—C1160.56 (8)C19—Fe2—C16—C20−37.36 (8)
C10—Fe1—C5—C1116.85 (8)C15—Fe2—C16—C2081.24 (10)
C4—Fe1—C5—C1−119.60 (12)C20—C16—C17—C181.70 (15)
C3—Fe1—C5—C1−81.70 (9)Fe2—C16—C17—C18−58.93 (10)
C2—Fe1—C5—C1−37.70 (8)C20—C16—C17—Fe260.62 (9)
C6—Fe1—C5—C175.48 (10)C13—Fe2—C17—C16160.10 (8)
C8—Fe1—C5—C1−165.77 (11)C12—Fe2—C17—C16118.83 (9)
C7—Fe1—C5—C143.6 (2)C18—Fe2—C17—C16−119.73 (11)
C9—Fe1—C6—C780.91 (8)C14—Fe2—C17—C16−172.60 (11)
C10—Fe1—C6—C7119.20 (10)C11—Fe2—C17—C1679.76 (9)
C4—Fe1—C6—C7157.18 (17)C19—Fe2—C17—C16−82.44 (9)
C3—Fe1—C6—C7−46.74 (16)C15—Fe2—C17—C1659.32 (19)
C5—Fe1—C6—C7−167.18 (8)C20—Fe2—C17—C16−38.44 (8)
C2—Fe1—C6—C7−82.52 (9)C16—Fe2—C17—C18119.73 (11)
C1—Fe1—C6—C7−125.48 (8)C13—Fe2—C17—C18−80.17 (9)
C8—Fe1—C6—C737.26 (8)C12—Fe2—C17—C18−121.44 (8)
C9—Fe1—C6—C10−38.29 (7)C14—Fe2—C17—C18−52.87 (15)
C4—Fe1—C6—C1038.0 (2)C11—Fe2—C17—C18−160.51 (7)
C3—Fe1—C6—C10−165.94 (12)C19—Fe2—C17—C1837.29 (7)
C5—Fe1—C6—C1073.62 (9)C15—Fe2—C17—C18179.06 (15)
C2—Fe1—C6—C10158.28 (7)C20—Fe2—C17—C1881.29 (8)
C1—Fe1—C6—C10115.32 (8)C16—C17—C18—C19−0.96 (16)
C8—Fe1—C6—C10−81.94 (8)Fe2—C17—C18—C19−59.52 (9)
C7—Fe1—C6—C10−119.20 (10)C16—C17—C18—Fe258.56 (9)
C10—C6—C7—C8−0.09 (15)C16—Fe2—C18—C1982.17 (9)
Fe1—C6—C7—C8−58.85 (10)C13—Fe2—C18—C19−125.62 (9)
C10—C6—C7—Fe158.76 (9)C12—Fe2—C18—C19−165.89 (8)
C9—Fe1—C7—C837.18 (8)C17—Fe2—C18—C19119.76 (11)
C10—Fe1—C7—C881.98 (8)C14—Fe2—C18—C19−84.92 (9)
C4—Fe1—C7—C8−44.97 (16)C11—Fe2—C18—C19169.15 (14)
C3—Fe1—C7—C8−80.62 (9)C15—Fe2—C18—C19−59.50 (16)
C5—Fe1—C7—C8160.65 (18)C20—Fe2—C18—C1937.83 (8)
C2—Fe1—C7—C8−123.76 (8)C16—Fe2—C18—C17−37.59 (7)
C1—Fe1—C7—C8−165.16 (8)C13—Fe2—C18—C17114.62 (8)
C6—Fe1—C7—C8119.99 (11)C12—Fe2—C18—C1774.35 (9)
C9—Fe1—C7—C6−82.82 (8)C14—Fe2—C18—C17155.32 (7)
C10—Fe1—C7—C6−38.01 (7)C11—Fe2—C18—C1749.39 (18)
C4—Fe1—C7—C6−164.96 (12)C19—Fe2—C18—C17−119.76 (11)
C3—Fe1—C7—C6159.39 (8)C15—Fe2—C18—C17−179.26 (12)
C5—Fe1—C7—C640.7 (2)C20—Fe2—C18—C17−81.93 (8)
C2—Fe1—C7—C6116.25 (8)C17—C18—C19—C20−0.16 (15)
C1—Fe1—C7—C674.85 (9)Fe2—C18—C19—C20−59.23 (9)
C8—Fe1—C7—C6−119.99 (11)C17—C18—C19—Fe259.07 (10)
C6—C7—C8—C90.79 (16)C16—Fe2—C19—C18−81.61 (9)
Fe1—C7—C8—C9−57.99 (9)C13—Fe2—C19—C1870.62 (10)
C6—C7—C8—Fe158.78 (9)C12—Fe2—C19—C1834.50 (19)
C10—Fe1—C8—C938.63 (8)C17—Fe2—C19—C18−37.55 (9)
C4—Fe1—C8—C9−80.38 (10)C14—Fe2—C19—C18113.65 (9)
C3—Fe1—C8—C9−122.86 (9)C11—Fe2—C19—C18−168.14 (16)
C5—Fe1—C8—C9−47.92 (16)C15—Fe2—C19—C18155.86 (9)
C2—Fe1—C8—C9−163.63 (9)C20—Fe2—C19—C18−119.27 (12)
C1—Fe1—C8—C9166.54 (18)C16—Fe2—C19—C2037.65 (7)
C6—Fe1—C8—C982.88 (9)C13—Fe2—C19—C20−170.11 (7)
C7—Fe1—C8—C9120.17 (12)C12—Fe2—C19—C20153.77 (14)
C9—Fe1—C8—C7−120.17 (12)C17—Fe2—C19—C2081.71 (8)
C10—Fe1—C8—C7−81.53 (8)C18—Fe2—C19—C20119.27 (12)
C4—Fe1—C8—C7159.45 (8)C14—Fe2—C19—C20−127.08 (8)
C3—Fe1—C8—C7116.97 (9)C11—Fe2—C19—C20−48.9 (2)
C5—Fe1—C8—C7−168.09 (11)C15—Fe2—C19—C20−84.87 (9)
C2—Fe1—C8—C776.20 (10)C18—C19—C20—C161.20 (14)
C1—Fe1—C8—C746.4 (2)Fe2—C19—C20—C16−57.75 (9)
C6—Fe1—C8—C7−37.29 (8)C18—C19—C20—C24−177.82 (13)
C7—C8—C9—C10−1.17 (15)Fe2—C19—C20—C24123.23 (14)
Fe1—C8—C9—C10−59.84 (9)C18—C19—C20—Fe258.95 (9)
C7—C8—C9—Fe158.67 (9)C17—C16—C20—C19−1.79 (14)
C10—Fe1—C9—C8−118.69 (12)Fe2—C16—C20—C1958.47 (9)
C4—Fe1—C9—C8116.24 (9)C17—C16—C20—C24177.35 (11)
C3—Fe1—C9—C875.66 (10)Fe2—C16—C20—C24−122.40 (12)
C5—Fe1—C9—C8158.02 (8)C17—C16—C20—Fe2−60.26 (9)
C2—Fe1—C9—C847.3 (2)C16—Fe2—C20—C19−119.85 (11)
C1—Fe1—C9—C8−171.00 (13)C13—Fe2—C20—C1928.3 (2)
C6—Fe1—C9—C8−80.84 (9)C12—Fe2—C20—C19−155.26 (13)
C7—Fe1—C9—C8−37.17 (8)C17—Fe2—C20—C19−81.59 (9)
C4—Fe1—C9—C10−125.08 (8)C18—Fe2—C20—C19−37.57 (8)
C3—Fe1—C9—C10−165.66 (8)C14—Fe2—C20—C1973.83 (9)
C5—Fe1—C9—C10−83.29 (9)C11—Fe2—C20—C19162.05 (8)
C2—Fe1—C9—C10166.01 (17)C15—Fe2—C20—C19117.69 (8)
C1—Fe1—C9—C10−52.32 (17)C13—Fe2—C20—C16148.16 (17)
C6—Fe1—C9—C1037.85 (8)C12—Fe2—C20—C16−35.41 (17)
C8—Fe1—C9—C10118.69 (12)C17—Fe2—C20—C1638.26 (9)
C7—Fe1—C9—C1081.52 (8)C18—Fe2—C20—C1682.28 (9)
C7—C6—C10—C9−0.62 (15)C14—Fe2—C20—C16−166.32 (8)
Fe1—C6—C10—C958.70 (9)C11—Fe2—C20—C16−78.11 (9)
C7—C6—C10—C21−176.10 (13)C19—Fe2—C20—C16119.85 (11)
Fe1—C6—C10—C21−116.78 (14)C15—Fe2—C20—C16−122.46 (8)
C7—C6—C10—Fe1−59.32 (9)C16—Fe2—C20—C24113.45 (16)
C8—C9—C10—C61.11 (15)C13—Fe2—C20—C24−98.4 (2)
Fe1—C9—C10—C6−59.43 (9)C12—Fe2—C20—C2478.03 (18)
C8—C9—C10—C21177.07 (12)C17—Fe2—C20—C24151.71 (14)
Fe1—C9—C10—C21116.53 (12)C18—Fe2—C20—C24−164.27 (14)
C8—C9—C10—Fe160.54 (9)C14—Fe2—C20—C24−52.88 (15)
C9—Fe1—C10—C6119.10 (11)C11—Fe2—C20—C2435.34 (15)
C4—Fe1—C10—C6−167.41 (8)C19—Fe2—C20—C24−126.71 (15)
C3—Fe1—C10—C6160.81 (16)C15—Fe2—C20—C24−9.02 (14)
C5—Fe1—C10—C6−126.04 (8)N2—N1—C21—C101.94 (19)
C2—Fe1—C10—C6−50.38 (16)Zn1—N1—C21—C10179.04 (10)
C1—Fe1—C10—C6−83.65 (9)C6—C10—C21—N1−20.7 (2)
C8—Fe1—C10—C681.34 (8)C9—C10—C21—N1164.32 (13)
C7—Fe1—C10—C637.62 (7)Fe1—C10—C21—N1−111.71 (14)
C4—Fe1—C10—C973.49 (9)N1—N2—C22—N5−177.47 (11)
C3—Fe1—C10—C941.7 (2)N1—N2—C22—S12.54 (16)
C5—Fe1—C10—C9114.86 (8)C23—N5—C22—N29.22 (19)
C2—Fe1—C10—C9−169.48 (13)C23—N5—C22—S1−170.79 (11)
C1—Fe1—C10—C9157.25 (8)Zn1—S1—C22—N2−9.21 (12)
C6—Fe1—C10—C9−119.10 (11)Zn1—S1—C22—N5170.80 (10)
C8—Fe1—C10—C9−37.76 (8)N4—N3—C24—C20−0.55 (19)
C7—Fe1—C10—C9−81.48 (8)Zn1—N3—C24—C20178.95 (10)
C9—Fe1—C10—C21−114.94 (14)C19—C20—C24—N321.9 (2)
C4—Fe1—C10—C21−41.45 (12)C16—C20—C24—N3−156.98 (13)
C3—Fe1—C10—C21−73.2 (2)Fe2—C20—C24—N3117.22 (14)
C5—Fe1—C10—C21−0.08 (12)N3—N4—C25—N6177.34 (10)
C2—Fe1—C10—C2175.58 (18)N3—N4—C25—S2−0.90 (16)
C1—Fe1—C10—C2142.31 (12)C26—N6—C25—N4−2.80 (18)
C6—Fe1—C10—C21125.96 (13)C26—N6—C25—S2175.66 (10)
C8—Fe1—C10—C21−152.71 (12)Zn1—S2—C25—N4−4.92 (11)
C7—Fe1—C10—C21163.57 (12)Zn1—S2—C25—N6176.83 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N4i0.822.132.9460 (16)178
N5—H2···O1ii0.842.062.8714 (17)162
C18—H18A···O1iii0.982.493.4065 (19)156
C1—H1A···Cg3iv0.982.843.6176 (15)137
C11—H11A···Cg1v0.982.583.4280 (15)145
C12—H12A···Cg5iii0.982.683.6607 (14)175
C27—H27A···Cg4i0.962.793.3830 (18)121
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x−1, y, z; (v) −x+1, y+1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N4i0.822.132.9460 (16)178
N5—H2···O1ii0.842.062.8714 (17)162
C18—H18A···O1iii0.982.493.4065 (19)156
C1—H1A···Cg3iv0.982.843.6176 (15)137
C11—H11A···Cg1v0.982.583.4280 (15)145
C12—H12A···Cg5iii0.982.683.6607 (14)175
C27—H27A···Cg4i0.962.793.3830 (18)121
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x−1, y, z; (v) −x+1, y+1/2, −z+3/2.
Acknowledgements top

HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CKQ thanks USM for a Research Fellowship.

references
References top

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