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Acta Cryst. (2009). E65, m1524-m1525    [ doi:10.1107/S1600536809046078 ]

Bis(1-ferrocenylmethylidene-4-phenylthiosemicarbazidato-[kappa]2N1,S)zinc(II) monohydrate

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

Abstract top

In the title compound, [Fe2Zn(C5H5)2(C13H11N3S)2]·H2O, the ZnII ion is in a distorted tetrahedral geometry being coordinated by two thiosemicarbazone ligands via N and S atoms. One of the Cp rings is disordered over two positions with occupancies of 0.55 and 0.45. The dihedral angle between the substituted Cp rings is 56.1 (5)° and the two phenyl rings are orientated at a dihedral angle of 41.7 (4)°. In the crystal structure, intermolecular O-H...S, N-H...O and C-H...N hydrogen bonds link the molecules into chains along the b axis. The structure is further consolidated by O-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-phenyllthiosemicarbazone.

The ZnII ion is in a distorted tetrahedral geometry being coordinated by two thiosemicarbarzone ligands via the N and S atoms (Fig. 1). The bond lengths and angles are comparable to those observed in closely related structures (Vikneswaran et al., 2009a,b). One of the Cp rings is disordered over two positions with site occupancies of 0.55 and 0.45. The Cp rings of each ferrocene residue are nearly parallel, with dihedral angles of Cp1/Cp2 [C1–C5/C6–C10] = 2.6 (5)°, Cp3/Cp5 [C11A–C15A/C16–C20] = 4.5 (14)° and Cp4/Cp5 [C11B–C15B/C16–C20] = 7.4 (16)°. The dihedral angle between the substituted Cp rings [Cp2 and Cp5] is 56.1 (5)° and the two phenyl rings [C23–C28 and C31–C36] are orientated at 41.7 (4)°.

In the crystal structure, intermolecular O—H···S, N—H···O and C—H···N hydrogen bonds (Table 1) link the molecules into chains along the b axis (Fig. 2). The crystal structure is further consolidated by O—H···π interactions involving the C1–C5 ring.

Related literature top

For related structures, see: Vikneswaran et al. (2009a,b). For the preparation, see: Casas et al. (2004). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the C1–C5 ring.

Experimental top

Formylferrocene 4-phenylthiosemicarbazone was prepared as described by Casas et al. (2004). 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-phenylthiosemicarbazone (0.36 g, 1 mmol) and KOH (0.12 g, 2 mmol) in absolute methanol (15 ml). Amorphous orange solid 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

One of the Cp rings is disordered over two positions with site occupancies of 0.55 and 0.45. The same Uij parameters is used for the atom pair C14A/C14B, and all disordered atoms were subjected to rigid bond and similarity restraints. All H-atoms were placed in calculated positions, with C–H = 0.93–0.98 Å, N–H = 0.86 and O–H = 0.85 and refined using a riding model, with Uiso(H) = 1.2 Ueq(C,N) and 1.5Ueq(O). The highest residual density peak is located 0.87 Å from atom Zn1 and the deepest hole is located 1.30 Å from atom Zn1.

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. All disorder components are shown.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the c axis, showing chains along b axis. Intermolecular hydrogen bonds are shown as dashed lines. Only the major disorder components are shown.
Bis(1-ferrocenylmethylidene-4-phenylthiosemicarbazidato- κ2N1,S)zinc(II) monohydrate top
Crystal data top
[Fe2Zn(C5H5)2(C13H11N3S)2]·H2OF(000) = 828
Mr = 807.88Dx = 1.585 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7082 reflections
a = 10.4500 (5) Åθ = 2.4–30.1°
b = 10.4892 (5) ŵ = 1.71 mm−1
c = 15.9377 (7) ÅT = 100 K
β = 104.277 (2)°Needle, brown
V = 1693.01 (14) Å30.65 × 0.17 × 0.09 mm
Z = 2
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		7565 independent reflections
Radiation source: fine-focus sealed tube5980 reflections with I > 2σ(I)
graphiteRint = 0.050
φ and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −13→13
Tmin = 0.402, Tmax = 0.858k = −13→13
17262 measured reflectionsl = −20→20
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.174 w = 1/[σ2(Fo2) + (0.0767P)2 + 6.158P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
7565 reflectionsΔρmax = 2.43 e Å−3
473 parametersΔρmin = −0.71 e Å−3
163 restraintsAbsolute structure: Flack (1983), 3458 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.50 (2)
Crystal data top
[Fe2Zn(C5H5)2(C13H11N3S)2]·H2OV = 1693.01 (14) Å3
Mr = 807.88Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.4500 (5) ŵ = 1.71 mm−1
b = 10.4892 (5) ÅT = 100 K
c = 15.9377 (7) Å0.65 × 0.17 × 0.09 mm
β = 104.277 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		7565 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		5980 reflections with I > 2σ(I)
Tmin = 0.402, Tmax = 0.858Rint = 0.050
17262 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.174Δρmax = 2.43 e Å−3
S = 1.09Δρmin = −0.71 e Å−3
7565 reflectionsAbsolute structure: Flack (1983), 3458 Friedel pairs
473 parametersFlack parameter: 0.50 (2)
163 restraints
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*/UeqOcc. (<1)
Zn10.68442 (7)−0.01485 (8)0.26651 (5)0.02324 (19)
Fe10.12446 (9)−0.05464 (9)0.06968 (6)0.0193 (2)
Fe20.63054 (10)−0.01196 (12)0.62280 (7)0.0290 (2)
S10.75745 (19)−0.21576 (18)0.25244 (13)0.0247 (4)
S20.7687 (2)0.17743 (18)0.24276 (12)0.0252 (4)
N10.5012 (5)−0.0784 (6)0.2047 (4)0.0243 (14)
N20.4886 (6)−0.2052 (6)0.1768 (4)0.0237 (13)
N30.5994 (6)−0.3911 (6)0.1667 (4)0.0255 (13)
H3B0.6710−0.43270.18800.031*
N40.6628 (6)0.0603 (6)0.3798 (4)0.0271 (14)
N50.7259 (7)0.1747 (6)0.4074 (4)0.0288 (14)
N60.8466 (7)0.3400 (6)0.3717 (4)0.0290 (14)
H6B0.87630.37520.33150.035*
C10.0105 (9)0.0322 (9)−0.0384 (6)0.0346 (19)
H1A−0.07190.0784−0.04100.042*
C20.0203 (11)−0.0972 (9)−0.0521 (5)0.041 (2)
H2A−0.0525−0.1582−0.06870.049*
C30.1618 (11)−0.1233 (10)−0.0410 (5)0.043 (3)
H3A0.2006−0.2066−0.04760.052*
C40.2298 (8)−0.0139 (11)−0.0172 (5)0.040 (2)
H4A0.3260−0.0046−0.00430.048*
C50.1380 (10)0.0859 (9)−0.0156 (7)0.042 (2)
H5A0.15950.1756−0.00140.051*
C60.1992 (8)−0.1840 (7)0.1668 (4)0.0254 (16)
H6A0.2461−0.26310.16070.031*
C70.0600 (8)−0.1709 (8)0.1560 (5)0.0258 (16)
H7A−0.0055−0.23930.14070.031*
C80.0331 (7)−0.0438 (8)0.1694 (4)0.0277 (17)
H8A−0.0550−0.00820.16510.033*
C90.1525 (8)0.0270 (8)0.1892 (5)0.0284 (17)
H9A0.16120.11840.20210.034*
C100.2585 (7)−0.0599 (8)0.1873 (4)0.0228 (14)
C11A0.664 (3)−0.157 (2)0.7124 (14)0.046 (5)0.55
H11A0.5996−0.20500.73540.055*0.55
C12A0.739 (2)−0.047 (2)0.7480 (12)0.050 (5)0.55
H12A0.7269−0.00070.79880.059*0.55
C13A0.823 (2)−0.009 (3)0.7001 (18)0.059 (5)0.55
H13A0.88170.06510.71160.070*0.55
C14A0.806 (5)−0.090 (5)0.629 (3)0.048 (4)0.55
H14A0.8541−0.08460.58320.057*0.55
C15A0.711 (3)−0.180 (3)0.6317 (16)0.053 (5)0.55
H15A0.6833−0.25100.59100.064*0.55
C11B0.623 (3)−0.194 (2)0.671 (2)0.048 (5)0.45
H11B0.5449−0.24350.67310.057*0.45
C12B0.696 (3)−0.106 (3)0.7340 (16)0.046 (6)0.45
H12B0.6720−0.08470.78820.056*0.45
C13B0.801 (3)−0.058 (3)0.7100 (17)0.045 (5)0.45
H13B0.86500.00230.74330.055*0.45
C14B0.804 (6)−0.112 (6)0.630 (3)0.048 (4)0.45
H14B0.8687−0.09110.59710.057*0.45
C15B0.700 (3)−0.197 (3)0.603 (2)0.048 (5)0.45
H15B0.6789−0.24620.54900.058*0.45
C160.4511 (8)0.0066 (11)0.5369 (5)0.044 (2)
H16A0.3927−0.06330.51050.052*
C170.4488 (8)0.0706 (10)0.6144 (6)0.040 (2)
H17A0.38980.05060.65180.048*
C180.5481 (10)0.1664 (8)0.6309 (5)0.035 (2)
H18A0.56900.22430.68070.042*
C190.6136 (10)0.1610 (8)0.5606 (6)0.038 (2)
H19A0.68710.21520.55450.045*
C200.5551 (8)0.0624 (8)0.5032 (5)0.0302 (17)
C210.3959 (7)−0.0207 (8)0.2059 (4)0.0255 (14)
H21A0.40890.06440.22210.031*
C220.5997 (7)−0.2673 (7)0.1942 (4)0.0213 (14)
C230.5015 (7)−0.4607 (7)0.1095 (5)0.0223 (16)
C240.5092 (8)−0.5925 (7)0.1105 (6)0.0274 (17)
H24A0.5747−0.63290.15210.033*
C250.4193 (8)−0.6661 (7)0.0495 (6)0.0302 (19)
H25A0.4245−0.75460.05150.036*
C260.3228 (8)−0.6063 (7)−0.0138 (5)0.0253 (17)
H26A0.2644−0.6541−0.05550.030*
C270.3147 (8)−0.4760 (7)−0.0141 (5)0.0241 (16)
H27A0.2491−0.4358−0.05580.029*
C280.4022 (8)−0.4026 (7)0.0464 (5)0.0222 (16)
H28A0.3946−0.31420.04490.027*
C290.5868 (8)0.0136 (8)0.4260 (5)0.0324 (18)
H29A0.5465−0.06340.40610.039*
C300.7787 (7)0.2288 (7)0.3500 (5)0.0225 (15)
C310.8740 (8)0.4042 (7)0.4519 (5)0.0243 (17)
C320.8949 (8)0.3425 (8)0.5310 (5)0.0253 (17)
H32A0.89340.25390.53310.030*
C330.9182 (8)0.4126 (8)0.6074 (6)0.0302 (19)
H33A0.92840.37140.66030.036*
C340.9261 (9)0.5440 (9)0.6041 (6)0.033 (2)
H34A0.94360.59160.65490.040*
C350.9081 (9)0.6034 (8)0.5260 (6)0.034 (2)
H35A0.91300.69180.52420.041*
C360.8830 (8)0.5354 (8)0.4500 (5)0.0267 (17)
H36A0.87210.57770.39750.032*
O1W0.8714 (7)0.5034 (10)0.2277 (5)0.071 (2)
H1W10.93160.51160.20070.106*
H2W10.87860.56510.26320.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0222 (4)0.0288 (4)0.0219 (4)−0.0055 (4)0.0114 (3)−0.0074 (4)
Fe10.0191 (5)0.0176 (5)0.0253 (5)−0.0014 (4)0.0134 (4)−0.0020 (4)
Fe20.0297 (5)0.0316 (5)0.0304 (5)0.0039 (5)0.0166 (4)−0.0003 (5)
S10.0212 (9)0.0285 (10)0.0244 (10)−0.0052 (7)0.0058 (7)0.0007 (7)
S20.0308 (11)0.0247 (9)0.0213 (9)−0.0009 (8)0.0088 (8)−0.0051 (7)
N10.011 (3)0.041 (4)0.024 (3)−0.005 (3)0.010 (2)−0.006 (3)
N20.028 (3)0.023 (3)0.024 (3)−0.002 (3)0.015 (3)−0.005 (2)
N30.022 (3)0.021 (3)0.034 (3)0.001 (3)0.009 (3)−0.002 (3)
N40.029 (3)0.028 (4)0.026 (3)−0.008 (3)0.011 (3)−0.009 (3)
N50.033 (4)0.025 (3)0.030 (3)−0.003 (3)0.011 (3)−0.008 (3)
N60.042 (4)0.026 (3)0.021 (3)−0.006 (3)0.013 (3)−0.004 (3)
C10.030 (4)0.041 (5)0.038 (5)0.009 (4)0.018 (4)0.011 (4)
C20.064 (7)0.041 (5)0.018 (4)−0.011 (4)0.010 (4)0.004 (3)
C30.065 (7)0.041 (5)0.024 (4)0.024 (5)0.011 (4)0.000 (4)
C40.032 (4)0.063 (6)0.033 (4)0.010 (5)0.022 (3)0.007 (5)
C50.053 (6)0.024 (4)0.059 (6)−0.001 (4)0.031 (5)0.012 (4)
C60.030 (4)0.030 (4)0.017 (3)−0.003 (3)0.007 (3)0.001 (3)
C70.034 (4)0.027 (4)0.021 (4)−0.003 (3)0.014 (3)0.003 (3)
C80.019 (3)0.043 (5)0.025 (3)0.002 (3)0.012 (3)0.005 (3)
C90.034 (4)0.025 (4)0.026 (4)0.007 (3)0.009 (3)−0.009 (3)
C100.019 (3)0.027 (3)0.024 (3)0.000 (3)0.008 (3)−0.006 (3)
C11A0.082 (14)0.028 (12)0.028 (10)0.015 (8)0.017 (9)0.008 (7)
C12A0.067 (12)0.038 (12)0.034 (7)0.026 (9)−0.005 (7)−0.005 (7)
C13A0.043 (10)0.044 (13)0.077 (11)0.013 (8)−0.007 (8)−0.014 (10)
C14A0.029 (4)0.055 (13)0.060 (5)0.018 (7)0.012 (4)−0.009 (7)
C15A0.072 (12)0.042 (11)0.053 (12)0.009 (8)0.030 (11)−0.013 (9)
C11B0.050 (11)0.021 (10)0.073 (15)0.009 (8)0.016 (10)0.009 (10)
C12B0.054 (14)0.045 (18)0.043 (11)0.019 (11)0.019 (10)0.003 (10)
C13B0.045 (11)0.047 (15)0.040 (9)0.001 (9)0.002 (8)−0.001 (10)
C14B0.029 (4)0.055 (13)0.060 (5)0.018 (7)0.012 (4)−0.009 (7)
C15B0.051 (10)0.031 (11)0.061 (14)0.014 (7)0.010 (11)−0.019 (11)
C160.032 (4)0.073 (7)0.030 (4)−0.015 (5)0.014 (3)−0.016 (5)
C170.026 (4)0.064 (6)0.037 (5)0.005 (4)0.019 (4)−0.003 (4)
C180.058 (6)0.028 (4)0.025 (4)0.016 (4)0.020 (4)−0.001 (3)
C190.050 (5)0.032 (5)0.038 (5)0.003 (4)0.024 (4)−0.001 (4)
C200.030 (4)0.035 (4)0.030 (4)−0.002 (3)0.015 (3)−0.005 (3)
C210.032 (4)0.020 (3)0.028 (3)−0.005 (3)0.013 (3)−0.004 (3)
C220.017 (3)0.028 (4)0.019 (3)0.000 (3)0.006 (3)0.006 (3)
C230.013 (4)0.036 (4)0.023 (4)−0.007 (3)0.013 (3)−0.006 (3)
C240.028 (4)0.019 (4)0.038 (5)0.000 (3)0.014 (4)−0.001 (3)
C250.042 (5)0.007 (3)0.046 (5)0.005 (3)0.020 (4)−0.005 (3)
C260.032 (4)0.017 (3)0.029 (4)−0.005 (3)0.012 (3)−0.005 (3)
C270.033 (4)0.018 (4)0.024 (4)−0.004 (3)0.013 (3)−0.004 (3)
C280.030 (4)0.010 (3)0.030 (4)−0.007 (3)0.014 (3)−0.002 (3)
C290.036 (4)0.032 (5)0.032 (4)−0.011 (3)0.015 (3)−0.011 (3)
C300.026 (4)0.020 (3)0.022 (4)0.002 (3)0.007 (3)−0.003 (3)
C310.025 (4)0.019 (3)0.029 (4)0.002 (3)0.009 (3)−0.010 (3)
C320.025 (4)0.020 (4)0.032 (4)0.003 (3)0.009 (3)−0.003 (3)
C330.014 (4)0.038 (5)0.037 (5)−0.004 (3)0.005 (3)−0.008 (4)
C340.033 (5)0.039 (5)0.032 (5)−0.003 (4)0.015 (4)−0.017 (4)
C350.038 (5)0.025 (4)0.042 (5)−0.010 (3)0.013 (4)−0.015 (4)
C360.019 (4)0.037 (4)0.026 (4)0.000 (3)0.009 (3)0.000 (3)
O1W0.067 (5)0.091 (7)0.062 (4)0.013 (5)0.031 (4)0.006 (5)
Geometric parameters (Å, °) top
Zn1—N42.033 (6)C9—H9A0.98
Zn1—N12.038 (6)C10—C211.452 (9)
Zn1—S22.270 (2)C11A—C12A1.43 (3)
Zn1—S12.271 (2)C11A—C15A1.51 (2)
Fe1—C42.016 (7)C11A—H11A0.98
Fe1—C22.027 (9)C12A—C13A1.36 (3)
Fe1—C32.030 (9)C12A—H12A0.98
Fe1—C52.033 (9)C13A—C14A1.398 (19)
Fe1—C92.042 (7)C13A—H13A0.98
Fe1—C102.046 (7)C14A—C15A1.38 (2)
Fe1—C82.049 (6)C14A—H14A0.9800
Fe1—C12.050 (9)C15A—H15A0.98
Fe1—C62.062 (7)C11B—C12B1.43 (3)
Fe1—C72.072 (7)C11B—C15B1.50 (3)
Fe2—C15A1.95 (4)C11B—H11B0.98
Fe2—C14A1.99 (6)C12B—C13B1.35 (3)
Fe2—C12B2.00 (3)C12B—H12B0.98
Fe2—C13B2.03 (3)C13B—C14B1.40 (2)
Fe2—C202.030 (9)C13B—H13B0.98
Fe2—C162.040 (8)C14B—C15B1.39 (2)
Fe2—C11A2.053 (19)C14B—H14B0.98
Fe2—C192.054 (9)C15B—H15B0.98
Fe2—C11B2.06 (2)C16—C171.412 (12)
Fe2—C172.061 (8)C16—C201.449 (11)
Fe2—C14B2.07 (7)C16—H16A0.98
Fe2—C12A2.071 (18)C17—C181.421 (13)
S1—C221.766 (7)C17—H17A0.98
S2—C301.771 (7)C18—C191.452 (11)
N1—C211.259 (9)C18—H18A0.98
N1—N21.398 (9)C19—C201.415 (12)
N2—C221.301 (9)C19—H19A0.98
N3—C221.370 (10)C20—C291.444 (10)
N3—C231.397 (9)C21—H21A0.93
N3—H3B0.86C23—C241.385 (11)
N4—C291.305 (10)C23—C281.394 (11)
N4—N51.388 (9)C24—C251.404 (12)
N5—C301.308 (10)C24—H24A0.93
N6—C301.364 (10)C25—C261.388 (12)
N6—C311.411 (9)C25—H25A0.93
N6—H6B0.86C26—C271.369 (11)
C1—C21.382 (13)C26—H26A0.93
C1—C51.409 (13)C27—C281.387 (10)
C1—H1A0.98C27—H27A0.93
C2—C31.471 (14)C28—H28A0.93
C2—H2A0.98C29—H29A0.93
C3—C41.353 (15)C31—C361.381 (11)
C3—H3A0.98C31—C321.386 (11)
C4—C51.425 (13)C32—C331.391 (11)
C4—H4A0.98C32—H32A0.93
C5—H5A0.98C33—C341.383 (12)
C6—C71.429 (11)C33—H33A0.93
C6—C101.444 (11)C34—C351.362 (13)
C6—H6A0.98C34—H34A0.93
C7—C81.389 (12)C35—C361.374 (11)
C7—H7A0.98C35—H35A0.93
C8—C91.418 (11)C36—H36A0.93
C8—H8A0.98O1W—H1W10.85
C9—C101.441 (10)O1W—H2W10.85
N4—Zn1—N1105.0 (2)C7—C6—H6A126.0
N4—Zn1—S286.35 (19)C10—C6—H6A126.0
N1—Zn1—S2124.5 (2)Fe1—C6—H6A126.0
N4—Zn1—S1124.1 (2)C8—C7—C6108.2 (7)
N1—Zn1—S187.0 (2)C8—C7—Fe169.4 (4)
S2—Zn1—S1130.88 (7)C6—C7—Fe169.4 (4)
C4—Fe1—C269.2 (4)C8—C7—H7A125.9
C4—Fe1—C339.1 (4)C6—C7—H7A125.9
C2—Fe1—C342.5 (4)Fe1—C7—H7A125.9
C4—Fe1—C541.2 (4)C7—C8—C9109.7 (7)
C2—Fe1—C568.2 (4)C7—C8—Fe171.2 (4)
C3—Fe1—C567.5 (4)C9—C8—Fe169.5 (4)
C4—Fe1—C9125.1 (4)C7—C8—H8A125.2
C2—Fe1—C9154.8 (4)C9—C8—H8A125.2
C3—Fe1—C9160.9 (4)Fe1—C8—H8A125.2
C5—Fe1—C9107.5 (4)C8—C9—C10107.7 (7)
C4—Fe1—C10105.6 (3)C8—C9—Fe170.0 (4)
C2—Fe1—C10163.0 (4)C10—C9—Fe169.5 (4)
C3—Fe1—C10123.5 (3)C8—C9—H9A126.2
C5—Fe1—C10119.1 (4)C10—C9—H9A126.2
C9—Fe1—C1041.3 (3)Fe1—C9—H9A126.2
C4—Fe1—C8163.5 (4)C9—C10—C6106.6 (6)
C2—Fe1—C8120.8 (4)C9—C10—C21123.0 (7)
C3—Fe1—C8156.9 (4)C6—C10—C21130.4 (7)
C5—Fe1—C8126.9 (4)C9—C10—Fe169.2 (4)
C9—Fe1—C840.6 (3)C6—C10—Fe170.0 (4)
C10—Fe1—C868.6 (3)C21—C10—Fe1126.8 (5)
C4—Fe1—C168.4 (3)C12A—C11A—C15A101.9 (16)
C2—Fe1—C139.6 (4)C12A—C11A—Fe270.4 (11)
C3—Fe1—C167.9 (4)C15A—C11A—Fe264.1 (15)
C5—Fe1—C140.4 (4)C12A—C11A—H11A129.0
C9—Fe1—C1121.2 (3)C15A—C11A—H11A129.0
C10—Fe1—C1155.0 (3)Fe2—C11A—H11A129.0
C8—Fe1—C1110.0 (3)C13A—C12A—C11A112.5 (17)
C4—Fe1—C6119.0 (3)C13A—C12A—Fe271.5 (12)
C2—Fe1—C6126.1 (3)C11A—C12A—Fe269.0 (11)
C3—Fe1—C6107.5 (3)C13A—C12A—H12A123.7
C5—Fe1—C6154.5 (4)C11A—C12A—H12A123.7
C9—Fe1—C668.6 (3)Fe2—C12A—H12A123.7
C10—Fe1—C641.2 (3)C12A—C13A—C14A107.9 (19)
C8—Fe1—C667.5 (3)C12A—C13A—Fe270.4 (12)
C1—Fe1—C6163.2 (3)C14A—C13A—Fe266 (2)
C4—Fe1—C7154.6 (4)C12A—C13A—H13A126.0
C2—Fe1—C7108.7 (3)C14A—C13A—H13A126.0
C3—Fe1—C7122.1 (4)Fe2—C13A—H13A126.0
C5—Fe1—C7163.4 (3)C15A—C14A—C13A109.7 (16)
C9—Fe1—C767.8 (3)C15A—C14A—Fe268 (2)
C10—Fe1—C768.7 (3)C13A—C14A—Fe274 (2)
C8—Fe1—C739.4 (3)C13A—C14A—H14A125.2
C1—Fe1—C7127.1 (3)Fe2—C14A—H14A125.2
C6—Fe1—C740.5 (3)C14A—C15A—C11A107.9 (18)
C15A—Fe2—C14A41.1 (11)C14A—C15A—Fe271 (3)
C15A—Fe2—C12B55.9 (10)C11A—C15A—Fe271.7 (14)
C14A—Fe2—C12B69.3 (15)C14A—C15A—H15A126.0
C15A—Fe2—C13B56.2 (13)C11A—C15A—H15A126.0
C14A—Fe2—C13B39.5 (15)Fe2—C15A—H15A126.0
C12B—Fe2—C13B39.1 (8)C12B—C11B—C15B103.8 (18)
C15A—Fe2—C20118.6 (8)C12B—C11B—Fe266.9 (15)
C14A—Fe2—C20110.0 (13)C15B—C11B—Fe271.2 (15)
C12B—Fe2—C20172.8 (9)C12B—C11B—H11B128.0
C13B—Fe2—C20143.9 (7)C15B—C11B—H11B128.0
C15A—Fe2—C16116.3 (9)Fe2—C11B—H11B128.0
C14A—Fe2—C16138.9 (10)C13B—C12B—C11B111.4 (18)
C12B—Fe2—C16134.3 (9)C13B—C12B—Fe271.6 (16)
C13B—Fe2—C16171.3 (9)C11B—C12B—Fe271.8 (15)
C20—Fe2—C1641.7 (3)C13B—C12B—H12B124.3
C15A—Fe2—C11A44.2 (8)C11B—C12B—H12B124.3
C14A—Fe2—C11A70.6 (14)Fe2—C12B—H12B124.3
C12B—Fe2—C11A19.1 (8)C12B—C13B—C14B108 (2)
C13B—Fe2—C11A51.5 (11)C12B—C13B—Fe269.3 (16)
C20—Fe2—C11A153.7 (8)C14B—C13B—Fe272 (3)
C16—Fe2—C11A120.4 (8)C12B—C13B—H13B126.0
C15A—Fe2—C19145.3 (7)C14B—C13B—H13B126.0
C14A—Fe2—C19110.9 (13)Fe2—C13B—H13B126.0
C12B—Fe2—C19146.7 (9)C15B—C14B—C13B110.6 (18)
C13B—Fe2—C19119.9 (8)C15B—C14B—Fe273 (3)
C20—Fe2—C1940.5 (4)C13B—C14B—Fe268 (2)
C16—Fe2—C1968.7 (4)C15B—C14B—H14B124.7
C11A—Fe2—C19165.4 (7)C13B—C14B—H14B124.7
C15A—Fe2—C11B35.7 (11)Fe2—C14B—H14B124.7
C14A—Fe2—C11B73.7 (14)C14B—C15B—C11B106.1 (18)
C12B—Fe2—C11B41.3 (9)C14B—C15B—Fe269 (3)
C13B—Fe2—C11B68.4 (11)C11B—C15B—Fe266.8 (13)
C20—Fe2—C11B131.4 (9)C14B—C15B—H15B126.9
C16—Fe2—C11B103.0 (9)C11B—C15B—H15B126.9
C11A—Fe2—C11B22.3 (6)Fe2—C15B—H15B126.9
C19—Fe2—C11B171.4 (9)C17—C16—C20107.9 (8)
C15A—Fe2—C17139.4 (8)C17—C16—Fe270.7 (5)
C14A—Fe2—C17178.9 (13)C20—C16—Fe268.8 (5)
C12B—Fe2—C17111.8 (7)C17—C16—H16A126.0
C13B—Fe2—C17141.5 (8)C20—C16—H16A126.0
C20—Fe2—C1768.9 (3)Fe2—C16—H16A126.0
C16—Fe2—C1740.3 (3)C16—C17—C18109.2 (7)
C11A—Fe2—C17110.5 (7)C16—C17—Fe269.1 (5)
C19—Fe2—C1768.2 (4)C18—C17—Fe270.5 (5)
C11B—Fe2—C17107.1 (7)C16—C17—H17A125.4
C15A—Fe2—C14B35.0 (15)C18—C17—H17A125.4
C14A—Fe2—C14B6(2)Fe2—C17—H17A125.4
C12B—Fe2—C14B66.3 (15)C17—C18—C19106.9 (7)
C13B—Fe2—C14B40.0 (11)C17—C18—Fe269.3 (5)
C20—Fe2—C14B112.3 (14)C19—C18—Fe268.6 (5)
C16—Fe2—C14B137.0 (11)C17—C18—H18A126.5
C11A—Fe2—C14B65.9 (16)C19—C18—H18A126.5
C19—Fe2—C14B116.4 (14)Fe2—C18—H18A126.5
C11B—Fe2—C14B67.8 (14)C20—C19—C18108.5 (8)
C17—Fe2—C14B174.4 (11)C20—C19—Fe268.8 (5)
C15A—Fe2—C12A69.1 (9)C18—C19—Fe270.3 (5)
C14A—Fe2—C12A66.5 (13)C20—C19—H19A125.8
C12B—Fe2—C12A21.7 (6)C18—C19—H19A125.8
C13B—Fe2—C12A28.0 (10)Fe2—C19—H19A125.8
C20—Fe2—C12A165.2 (8)C19—C20—C29131.0 (7)
C16—Fe2—C12A149.1 (8)C19—C20—C16107.5 (7)
C11A—Fe2—C12A40.5 (8)C29—C20—C16121.5 (7)
C19—Fe2—C12A125.7 (7)C19—C20—Fe270.6 (5)
C11B—Fe2—C12A62.6 (10)C29—C20—Fe2123.1 (6)
C17—Fe2—C12A114.5 (7)C16—C20—Fe269.5 (5)
C14B—Fe2—C12A65.9 (15)N1—C21—C10133.2 (7)
C22—S1—Zn192.5 (3)N1—C21—H21A113.4
C30—S2—Zn192.4 (3)C10—C21—H21A113.4
C21—N1—N2116.6 (6)N2—C22—N3118.4 (6)
C21—N1—Zn1123.7 (5)N2—C22—S1128.8 (6)
N2—N1—Zn1117.9 (4)N3—C22—S1112.8 (5)
C22—N2—N1113.6 (6)C24—C23—C28118.4 (8)
C22—N3—C23130.3 (6)C24—C23—N3118.9 (8)
C22—N3—H3B114.8C28—C23—N3122.5 (7)
C23—N3—H3B114.8C23—C24—C25120.9 (9)
C29—N4—N5117.0 (6)C23—C24—H24A119.6
C29—N4—Zn1124.9 (5)C25—C24—H24A119.6
N5—N4—Zn1117.9 (5)C26—C25—C24119.8 (7)
C30—N5—N4113.8 (6)C26—C25—H25A120.1
C30—N6—C31127.8 (7)C24—C25—H25A120.1
C30—N6—H6B116.1C27—C26—C25119.1 (8)
C31—N6—H6B116.1C27—C26—H26A120.4
C2—C1—C5109.4 (9)C25—C26—H26A120.4
C2—C1—Fe169.3 (5)C26—C27—C28121.5 (8)
C5—C1—Fe169.2 (5)C26—C27—H27A119.3
C2—C1—H1A125.3C28—C27—H27A119.3
C5—C1—H1A125.3C27—C28—C23120.3 (7)
Fe1—C1—H1A125.3C27—C28—H28A119.9
C1—C2—C3106.0 (9)C23—C28—H28A119.9
C1—C2—Fe171.1 (6)N4—C29—C20130.4 (7)
C3—C2—Fe168.9 (5)N4—C29—H29A114.8
C1—C2—H2A127.0C20—C29—H29A114.8
C3—C2—H2A127.0N5—C30—N6118.5 (6)
Fe1—C2—H2A127.0N5—C30—S2127.4 (6)
C4—C3—C2108.6 (8)N6—C30—S2114.0 (5)
C4—C3—Fe169.9 (5)C36—C31—C32119.2 (8)
C2—C3—Fe168.6 (5)C36—C31—N6117.1 (8)
C4—C3—H3A125.7C32—C31—N6123.6 (7)
C2—C3—H3A125.7C31—C32—C33120.3 (7)
Fe1—C3—H3A125.7C31—C32—H32A119.9
C3—C4—C5108.6 (7)C33—C32—H32A119.9
C3—C4—Fe171.0 (5)C34—C33—C32119.5 (9)
C5—C4—Fe170.1 (4)C34—C33—H33A120.2
C3—C4—H4A125.7C32—C33—H33A120.2
C5—C4—H4A125.7C35—C34—C33119.7 (8)
Fe1—C4—H4A125.7C35—C34—H34A120.2
C1—C5—C4107.4 (8)C33—C34—H34A120.2
C1—C5—Fe170.5 (5)C34—C35—C36121.4 (8)
C4—C5—Fe168.7 (5)C34—C35—H35A119.3
C1—C5—H5A126.3C36—C35—H35A119.3
C4—C5—H5A126.3C35—C36—C31119.8 (8)
Fe1—C5—H5A126.3C35—C36—H36A120.1
C7—C6—C10107.9 (7)C31—C36—H36A120.1
C7—C6—Fe170.1 (4)H1W1—O1W—H2W1107.7
C10—C6—Fe168.8 (4)
N4—Zn1—S1—C22108.9 (3)C20—Fe2—C14A—C13A129.2 (17)
N1—Zn1—S1—C222.8 (3)C16—Fe2—C14A—C13A166.9 (13)
S2—Zn1—S1—C22−132.1 (2)C11A—Fe2—C14A—C13A−79 (2)
N4—Zn1—S2—C3010.8 (3)C19—Fe2—C14A—C13A86 (2)
N1—Zn1—S2—C30116.5 (3)C11B—Fe2—C14A—C13A−102 (2)
S1—Zn1—S2—C30−122.8 (3)C14B—Fe2—C14A—C13A−118 (22)
N4—Zn1—N1—C2138.0 (7)C12A—Fe2—C14A—C13A−35.3 (16)
S2—Zn1—N1—C21−58.0 (6)C13A—C14A—C15A—C11A−1(5)
S1—Zn1—N1—C21162.6 (6)Fe2—C14A—C15A—C11A−63 (2)
N4—Zn1—N1—N2−126.5 (5)C13A—C14A—C15A—Fe262 (4)
S2—Zn1—N1—N2137.5 (4)C12A—C11A—C15A—C14A1(4)
S1—Zn1—N1—N2−1.9 (4)Fe2—C11A—C15A—C14A62 (4)
C21—N1—N2—C22−166.1 (6)C12A—C11A—C15A—Fe2−61.1 (15)
Zn1—N1—N2—C22−0.5 (7)C12B—Fe2—C15A—C14A−97 (2)
N1—Zn1—N4—C2937.5 (8)C13B—Fe2—C15A—C14A−50 (2)
S2—Zn1—N4—C29162.3 (7)C20—Fe2—C15A—C14A88.2 (18)
S1—Zn1—N4—C29−59.2 (7)C16—Fe2—C15A—C14A135.4 (17)
N1—Zn1—N4—N5−137.7 (5)C11A—Fe2—C15A—C14A−117 (2)
S2—Zn1—N4—N5−12.9 (5)C19—Fe2—C15A—C14A45 (2)
S1—Zn1—N4—N5125.6 (5)C11B—Fe2—C15A—C14A−150 (3)
C29—N4—N5—C30−167.1 (7)C17—Fe2—C15A—C14A178.4 (17)
Zn1—N4—N5—C308.5 (8)C14B—Fe2—C15A—C14A0(4)
C4—Fe1—C1—C283.1 (7)C12A—Fe2—C15A—C14A−77.8 (19)
C3—Fe1—C1—C240.8 (6)C14A—Fe2—C15A—C11A117 (2)
C5—Fe1—C1—C2121.6 (8)C12B—Fe2—C15A—C11A19.7 (14)
C9—Fe1—C1—C2−158.1 (6)C13B—Fe2—C15A—C11A67.3 (16)
C10—Fe1—C1—C2163.4 (7)C20—Fe2—C15A—C11A−154.8 (12)
C8—Fe1—C1—C2−114.5 (6)C16—Fe2—C15A—C11A−107.5 (13)
C6—Fe1—C1—C2−36.3 (14)C19—Fe2—C15A—C11A162.4 (13)
C7—Fe1—C1—C2−73.6 (7)C11B—Fe2—C15A—C11A−32.5 (13)
C4—Fe1—C1—C5−38.5 (6)C17—Fe2—C15A—C11A−64.5 (18)
C2—Fe1—C1—C5−121.6 (8)C14B—Fe2—C15A—C11A117 (3)
C3—Fe1—C1—C5−80.7 (6)C12A—Fe2—C15A—C11A39.2 (13)
C9—Fe1—C1—C580.4 (6)C15A—Fe2—C11B—C12B97 (2)
C10—Fe1—C1—C541.8 (9)C14A—Fe2—C11B—C12B77.0 (18)
C8—Fe1—C1—C5123.9 (5)C13B—Fe2—C11B—C12B35.6 (12)
C6—Fe1—C1—C5−157.9 (10)C20—Fe2—C11B—C12B179.6 (11)
C7—Fe1—C1—C5164.9 (5)C16—Fe2—C11B—C12B−145.4 (13)
C5—C1—C2—C3−2.8 (10)C11A—Fe2—C11B—C12B−1(2)
Fe1—C1—C2—C3−60.4 (6)C17—Fe2—C11B—C12B−103.8 (14)
C5—C1—C2—Fe157.6 (7)C14B—Fe2—C11B—C12B78.9 (16)
C4—Fe1—C2—C1−80.8 (6)C12A—Fe2—C11B—C12B5.4 (13)
C3—Fe1—C2—C1−116.4 (8)C15A—Fe2—C11B—C15B−17 (2)
C5—Fe1—C2—C1−36.5 (5)C14A—Fe2—C11B—C15B−37.7 (19)
C9—Fe1—C2—C148.6 (11)C12B—Fe2—C11B—C15B−115 (2)
C10—Fe1—C2—C1−155.7 (10)C13B—Fe2—C11B—C15B−79.2 (15)
C8—Fe1—C2—C184.5 (6)C20—Fe2—C11B—C15B64.8 (17)
C6—Fe1—C2—C1167.8 (5)C16—Fe2—C11B—C15B99.9 (15)
C7—Fe1—C2—C1126.1 (5)C11A—Fe2—C11B—C15B−116 (3)
C4—Fe1—C2—C335.5 (6)C17—Fe2—C11B—C15B141.4 (14)
C5—Fe1—C2—C379.9 (6)C14B—Fe2—C11B—C15B−35.9 (16)
C9—Fe1—C2—C3165.0 (8)C12A—Fe2—C11B—C15B−109.4 (17)
C10—Fe1—C2—C3−39.3 (14)C15B—C11B—C12B—C13B1(3)
C8—Fe1—C2—C3−159.1 (5)Fe2—C11B—C12B—C13B−61 (2)
C1—Fe1—C2—C3116.4 (8)C15B—C11B—C12B—Fe262 (2)
C6—Fe1—C2—C3−75.9 (6)C15A—Fe2—C12B—C13B76.6 (19)
C7—Fe1—C2—C3−117.5 (6)C14A—Fe2—C12B—C13B32 (2)
C1—C2—C3—C43.3 (10)C16—Fe2—C12B—C13B171.7 (14)
Fe1—C2—C3—C4−58.6 (6)C11A—Fe2—C12B—C13B123 (4)
C1—C2—C3—Fe161.9 (6)C19—Fe2—C12B—C13B−64 (2)
C2—Fe1—C3—C4120.5 (7)C11B—Fe2—C12B—C13B121 (2)
C5—Fe1—C3—C438.7 (5)C17—Fe2—C12B—C13B−147.6 (15)
C9—Fe1—C3—C4−39.8 (13)C14B—Fe2—C12B—C13B38.2 (14)
C10—Fe1—C3—C4−72.3 (6)C12A—Fe2—C12B—C13B−46 (3)
C8—Fe1—C3—C4171.8 (7)C15A—Fe2—C12B—C11B−44.4 (18)
C1—Fe1—C3—C482.5 (6)C14A—Fe2—C12B—C11B−88.5 (18)
C6—Fe1—C3—C4−114.8 (5)C13B—Fe2—C12B—C11B−121 (2)
C7—Fe1—C3—C4−156.7 (5)C16—Fe2—C12B—C11B50.7 (18)
C4—Fe1—C3—C2−120.5 (7)C11A—Fe2—C12B—C11B2(3)
C5—Fe1—C3—C2−81.9 (6)C19—Fe2—C12B—C11B174.6 (12)
C9—Fe1—C3—C2−160.3 (9)C17—Fe2—C12B—C11B91.4 (14)
C10—Fe1—C3—C2167.2 (5)C14B—Fe2—C12B—C11B−82.8 (14)
C8—Fe1—C3—C251.3 (10)C12A—Fe2—C12B—C11B−167 (3)
C1—Fe1—C3—C2−38.1 (5)C11B—C12B—C13B—C14B−1(5)
C6—Fe1—C3—C2124.7 (5)Fe2—C12B—C13B—C14B−62 (4)
C7—Fe1—C3—C282.8 (6)C11B—C12B—C13B—Fe261 (2)
C2—C3—C4—C5−2.5 (10)C15A—Fe2—C13B—C12B−75.7 (19)
Fe1—C3—C4—C5−60.3 (6)C14A—Fe2—C13B—C12B−128 (3)
C2—C3—C4—Fe157.8 (6)C20—Fe2—C13B—C12B−169.2 (14)
C2—Fe1—C4—C3−38.5 (5)C11A—Fe2—C13B—C12B−20.5 (14)
C5—Fe1—C4—C3−118.9 (7)C19—Fe2—C13B—C12B145.2 (15)
C9—Fe1—C4—C3165.2 (5)C11B—Fe2—C13B—C12B−37.5 (15)
C10—Fe1—C4—C3124.4 (5)C17—Fe2—C13B—C12B53 (2)
C8—Fe1—C4—C3−168.6 (10)C14B—Fe2—C13B—C12B−118 (3)
C1—Fe1—C4—C3−81.2 (6)C12A—Fe2—C13B—C12B34.5 (15)
C6—Fe1—C4—C382.1 (6)C15A—Fe2—C13B—C14B43 (2)
C7—Fe1—C4—C351.4 (10)C14A—Fe2—C13B—C14B−9(3)
C2—Fe1—C4—C580.4 (6)C12B—Fe2—C13B—C14B118 (3)
C3—Fe1—C4—C5118.9 (7)C20—Fe2—C13B—C14B−51 (2)
C9—Fe1—C4—C5−76.0 (6)C11A—Fe2—C13B—C14B98 (2)
C10—Fe1—C4—C5−116.7 (6)C19—Fe2—C13B—C14B−97 (2)
C8—Fe1—C4—C5−49.8 (13)C11B—Fe2—C13B—C14B81 (2)
C1—Fe1—C4—C537.7 (6)C17—Fe2—C13B—C14B171 (2)
C6—Fe1—C4—C5−159.0 (5)C12A—Fe2—C13B—C14B153 (3)
C7—Fe1—C4—C5170.3 (7)C12B—C13B—C14B—C15B−1(7)
C2—C1—C5—C41.4 (10)Fe2—C13B—C14B—C15B−61 (5)
Fe1—C1—C5—C459.0 (6)C12B—C13B—C14B—Fe260 (2)
C2—C1—C5—Fe1−57.6 (7)C15A—Fe2—C14B—C15B20.1 (19)
C3—C4—C5—C10.7 (10)C14A—Fe2—C14B—C15B−158 (23)
Fe1—C4—C5—C1−60.1 (6)C12B—Fe2—C14B—C15B84 (2)
C3—C4—C5—Fe160.9 (6)C13B—Fe2—C14B—C15B121 (3)
C4—Fe1—C5—C1118.6 (8)C20—Fe2—C14B—C15B−88 (2)
C2—Fe1—C5—C135.8 (6)C16—Fe2—C14B—C15B−46 (3)
C3—Fe1—C5—C181.9 (6)C11A—Fe2—C14B—C15B63 (2)
C9—Fe1—C5—C1−117.8 (5)C19—Fe2—C14B—C15B−133 (2)
C10—Fe1—C5—C1−161.2 (5)C11B—Fe2—C14B—C15B39 (2)
C8—Fe1—C5—C1−77.1 (6)C12A—Fe2—C14B—C15B108 (3)
C6—Fe1—C5—C1165.3 (7)C15A—Fe2—C14B—C13B−101 (3)
C7—Fe1—C5—C1−46.7 (15)C14A—Fe2—C14B—C13B81 (21)
C2—Fe1—C5—C4−82.8 (6)C12B—Fe2—C14B—C13B−37.3 (18)
C3—Fe1—C5—C4−36.7 (5)C20—Fe2—C14B—C13B150.4 (16)
C9—Fe1—C5—C4123.6 (6)C16—Fe2—C14B—C13B−167.7 (13)
C10—Fe1—C5—C480.2 (6)C11A—Fe2—C14B—C13B−58.2 (19)
C8—Fe1—C5—C4164.3 (5)C19—Fe2—C14B—C13B105.9 (19)
C1—Fe1—C5—C4−118.6 (8)C11B—Fe2—C14B—C13B−82 (2)
C6—Fe1—C5—C446.7 (11)C12A—Fe2—C14B—C13B−13.6 (16)
C7—Fe1—C5—C4−165.3 (11)C13B—C14B—C15B—C11B2(7)
C4—Fe1—C6—C7−160.3 (5)Fe2—C14B—C15B—C11B−56 (3)
C2—Fe1—C6—C7−76.0 (6)C13B—C14B—C15B—Fe258 (4)
C3—Fe1—C6—C7−119.4 (5)C12B—C11B—C15B—C14B−2(5)
C5—Fe1—C6—C7166.5 (8)Fe2—C11B—C15B—C14B58 (4)
C9—Fe1—C6—C780.5 (5)C12B—C11B—C15B—Fe2−59.4 (18)
C10—Fe1—C6—C7119.4 (6)C15A—Fe2—C15B—C14B−65 (6)
C8—Fe1—C6—C736.6 (4)C14A—Fe2—C15B—C14B3(4)
C1—Fe1—C6—C7−48.1 (13)C12B—Fe2—C15B—C14B−79 (3)
C4—Fe1—C6—C1080.3 (5)C13B—Fe2—C15B—C14B−37 (2)
C2—Fe1—C6—C10164.6 (5)C20—Fe2—C15B—C14B106 (2)
C3—Fe1—C6—C10121.2 (5)C16—Fe2—C15B—C14B149 (2)
C5—Fe1—C6—C1047.1 (10)C11A—Fe2—C15B—C14B−95 (3)
C9—Fe1—C6—C10−38.9 (4)C19—Fe2—C15B—C14B73 (3)
C8—Fe1—C6—C10−82.8 (4)C11B—Fe2—C15B—C14B−119 (3)
C1—Fe1—C6—C10−167.5 (10)C17—Fe2—C15B—C14B−178 (2)
C7—Fe1—C6—C10−119.4 (6)C12A—Fe2—C15B—C14B−62 (3)
C10—C6—C7—C8−0.2 (8)C15A—Fe2—C15B—C11B54 (6)
Fe1—C6—C7—C8−58.8 (5)C14A—Fe2—C15B—C11B123 (3)
C10—C6—C7—Fe158.6 (5)C12B—Fe2—C15B—C11B40.3 (14)
C4—Fe1—C7—C8163.3 (7)C13B—Fe2—C15B—C11B82.7 (16)
C2—Fe1—C7—C8−116.1 (5)C20—Fe2—C15B—C11B−135.1 (14)
C3—Fe1—C7—C8−161.1 (5)C16—Fe2—C15B—C11B−91.5 (15)
C5—Fe1—C7—C8−39.6 (15)C11A—Fe2—C15B—C11B24.6 (12)
C9—Fe1—C7—C837.2 (4)C19—Fe2—C15B—C11B−167.4 (13)
C10—Fe1—C7—C881.8 (5)C17—Fe2—C15B—C11B−59 (2)
C1—Fe1—C7—C8−75.9 (6)C14B—Fe2—C15B—C11B119 (3)
C6—Fe1—C7—C8119.8 (6)C12A—Fe2—C15B—C11B57.9 (16)
C4—Fe1—C7—C643.5 (10)C15A—Fe2—C16—C17136.6 (9)
C2—Fe1—C7—C6124.1 (5)C14A—Fe2—C16—C17−178.8 (18)
C3—Fe1—C7—C679.0 (6)C12B—Fe2—C16—C1769.6 (13)
C5—Fe1—C7—C6−159.5 (12)C20—Fe2—C16—C17−119.1 (9)
C9—Fe1—C7—C6−82.6 (5)C11A—Fe2—C16—C1786.2 (9)
C10—Fe1—C7—C6−38.0 (4)C19—Fe2—C16—C17−81.1 (6)
C8—Fe1—C7—C6−119.8 (6)C11B—Fe2—C16—C17101.2 (10)
C1—Fe1—C7—C6164.3 (5)C14B—Fe2—C16—C17173 (2)
C6—C7—C8—C9−0.2 (8)C12A—Fe2—C16—C1743.6 (15)
Fe1—C7—C8—C9−59.0 (5)C15A—Fe2—C16—C20−104.3 (9)
C6—C7—C8—Fe158.8 (5)C14A—Fe2—C16—C20−59.7 (19)
C4—Fe1—C8—C7−154.2 (10)C12B—Fe2—C16—C20−171.3 (12)
C2—Fe1—C8—C782.1 (5)C11A—Fe2—C16—C20−154.7 (8)
C3—Fe1—C8—C744.2 (10)C19—Fe2—C16—C2038.0 (5)
C5—Fe1—C8—C7166.8 (5)C11B—Fe2—C16—C20−139.7 (9)
C9—Fe1—C8—C7−120.5 (6)C17—Fe2—C16—C20119.1 (9)
C10—Fe1—C8—C7−82.1 (5)C14B—Fe2—C16—C20−68 (2)
C1—Fe1—C8—C7124.6 (5)C12A—Fe2—C16—C20162.7 (13)
C6—Fe1—C8—C7−37.6 (5)C20—C16—C17—C180.4 (11)
C4—Fe1—C8—C9−33.7 (13)Fe2—C16—C17—C1859.2 (7)
C2—Fe1—C8—C9−157.4 (5)C20—C16—C17—Fe2−58.9 (6)
C3—Fe1—C8—C9164.7 (8)C15A—Fe2—C17—C16−71.1 (13)
C5—Fe1—C8—C9−72.7 (6)C12B—Fe2—C17—C16−133.7 (11)
C10—Fe1—C8—C938.4 (5)C13B—Fe2—C17—C16−166.6 (13)
C1—Fe1—C8—C9−114.9 (5)C20—Fe2—C17—C1638.6 (6)
C6—Fe1—C8—C982.9 (5)C11A—Fe2—C17—C16−113.3 (9)
C7—Fe1—C8—C9120.5 (6)C19—Fe2—C17—C1682.3 (6)
C7—C8—C9—C100.5 (8)C11B—Fe2—C17—C16−90.0 (11)
Fe1—C8—C9—C10−59.5 (5)C12A—Fe2—C17—C16−157.1 (9)
C7—C8—C9—Fe160.0 (5)C15A—Fe2—C17—C18168.2 (12)
C4—Fe1—C9—C8168.9 (5)C12B—Fe2—C17—C18105.7 (11)
C2—Fe1—C9—C850.7 (10)C13B—Fe2—C17—C1872.8 (14)
C3—Fe1—C9—C8−161.6 (10)C20—Fe2—C17—C18−82.1 (5)
C5—Fe1—C9—C8126.8 (5)C16—Fe2—C17—C18−120.6 (8)
C10—Fe1—C9—C8−118.7 (7)C11A—Fe2—C17—C18126.1 (9)
C1—Fe1—C9—C884.7 (5)C19—Fe2—C17—C18−38.4 (5)
C6—Fe1—C9—C8−79.9 (5)C11B—Fe2—C17—C18149.4 (10)
C7—Fe1—C9—C8−36.2 (5)C12A—Fe2—C17—C1882.3 (9)
C4—Fe1—C9—C10−72.4 (6)C16—C17—C18—C190.1 (11)
C2—Fe1—C9—C10169.5 (7)Fe2—C17—C18—C1958.5 (6)
C3—Fe1—C9—C10−42.8 (13)C16—C17—C18—Fe2−58.4 (7)
C5—Fe1—C9—C10−114.5 (5)C14A—Fe2—C18—C17178.3 (19)
C8—Fe1—C9—C10118.7 (7)C12B—Fe2—C18—C17−93.1 (10)
C1—Fe1—C9—C10−156.5 (4)C13B—Fe2—C18—C17−137.4 (9)
C6—Fe1—C9—C1038.8 (5)C20—Fe2—C18—C1781.7 (5)
C7—Fe1—C9—C1082.5 (5)C16—Fe2—C18—C1736.8 (5)
C8—C9—C10—C6−0.6 (8)C11A—Fe2—C18—C17−75.5 (11)
Fe1—C9—C10—C6−60.4 (5)C19—Fe2—C18—C17118.8 (7)
C8—C9—C10—C21−179.0 (6)C11B—Fe2—C18—C17−48.0 (15)
Fe1—C9—C10—C21121.2 (7)C14B—Fe2—C18—C17−179 (2)
C8—C9—C10—Fe159.8 (5)C12A—Fe2—C18—C17−111.8 (9)
C7—C6—C10—C90.4 (8)C14A—Fe2—C18—C1959 (2)
Fe1—C6—C10—C959.9 (5)C12B—Fe2—C18—C19148.1 (10)
C7—C6—C10—C21178.7 (7)C13B—Fe2—C18—C19103.8 (9)
Fe1—C6—C10—C21−121.9 (7)C20—Fe2—C18—C19−37.1 (5)
C7—C6—C10—Fe1−59.4 (5)C16—Fe2—C18—C19−82.1 (6)
C4—Fe1—C10—C9125.9 (5)C11A—Fe2—C18—C19165.7 (11)
C2—Fe1—C10—C9−164.6 (11)C11B—Fe2—C18—C19−166.8 (14)
C3—Fe1—C10—C9164.5 (5)C17—Fe2—C18—C19−118.8 (7)
C5—Fe1—C10—C983.6 (5)C14B—Fe2—C18—C1962 (2)
C8—Fe1—C10—C9−37.8 (5)C12A—Fe2—C18—C19129.3 (9)
C1—Fe1—C10—C953.9 (8)C17—C18—C19—C20−0.5 (10)
C6—Fe1—C10—C9−117.6 (6)Fe2—C18—C19—C2058.4 (6)
C7—Fe1—C10—C9−80.2 (5)C17—C18—C19—Fe2−58.9 (6)
C4—Fe1—C10—C6−116.5 (5)C15A—Fe2—C19—C2066.8 (17)
C2—Fe1—C10—C6−47.1 (13)C14A—Fe2—C19—C2096.8 (10)
C3—Fe1—C10—C6−77.9 (6)C12B—Fe2—C19—C20−179.4 (13)
C5—Fe1—C10—C6−158.9 (5)C13B—Fe2—C19—C20139.5 (10)
C9—Fe1—C10—C6117.6 (6)C16—Fe2—C19—C20−39.1 (5)
C8—Fe1—C10—C679.8 (5)C11A—Fe2—C19—C20−170 (3)
C1—Fe1—C10—C6171.5 (7)C17—Fe2—C19—C20−82.5 (5)
C7—Fe1—C10—C637.4 (4)C14B—Fe2—C19—C2094.0 (12)
C4—Fe1—C10—C219.7 (8)C12A—Fe2—C19—C20172.3 (9)
C2—Fe1—C10—C2179.1 (14)C15A—Fe2—C19—C18−173.3 (16)
C3—Fe1—C10—C2148.2 (9)C14A—Fe2—C19—C18−143.3 (11)
C5—Fe1—C10—C21−32.7 (8)C12B—Fe2—C19—C18−59.5 (15)
C9—Fe1—C10—C21−116.3 (9)C13B—Fe2—C19—C18−100.5 (10)
C8—Fe1—C10—C21−154.0 (8)C20—Fe2—C19—C18120.0 (8)
C1—Fe1—C10—C21−62.4 (10)C16—Fe2—C19—C1880.9 (6)
C6—Fe1—C10—C21126.2 (8)C11A—Fe2—C19—C18−50 (3)
C7—Fe1—C10—C21163.5 (8)C17—Fe2—C19—C1837.5 (5)
C15A—Fe2—C11A—C12A114.6 (19)C14B—Fe2—C19—C18−146.0 (12)
C14A—Fe2—C11A—C12A76.3 (13)C12A—Fe2—C19—C18−67.8 (10)
C12B—Fe2—C11A—C12A−6(3)C18—C19—C20—C29−176.8 (9)
C13B—Fe2—C11A—C12A36.2 (17)Fe2—C19—C20—C29−117.4 (10)
C20—Fe2—C11A—C12A172.3 (12)C18—C19—C20—C160.8 (10)
C16—Fe2—C11A—C12A−147.7 (12)Fe2—C19—C20—C1660.1 (6)
C19—Fe2—C11A—C12A−22 (4)C18—C19—C20—Fe2−59.3 (6)
C11B—Fe2—C11A—C12A171 (3)C17—C16—C20—C19−0.7 (11)
C17—Fe2—C11A—C12A−104.2 (13)Fe2—C16—C20—C19−60.8 (6)
C14B—Fe2—C11A—C12A80.5 (18)C17—C16—C20—C29177.1 (8)
C14A—Fe2—C11A—C15A−38.3 (12)Fe2—C16—C20—C29117.0 (8)
C12B—Fe2—C11A—C15A−121 (4)C17—C16—C20—Fe260.1 (7)
C13B—Fe2—C11A—C15A−78.4 (18)C15A—Fe2—C20—C19−143.4 (10)
C20—Fe2—C11A—C15A58 (2)C14A—Fe2—C20—C19−99.1 (10)
C16—Fe2—C11A—C15A97.7 (13)C13B—Fe2—C20—C19−72.5 (16)
C19—Fe2—C11A—C15A−137 (3)C16—Fe2—C20—C19118.1 (7)
C11B—Fe2—C11A—C15A56 (3)C11A—Fe2—C20—C19174.4 (15)
C17—Fe2—C11A—C15A141.2 (13)C11B—Fe2—C20—C19175.4 (10)
C14B—Fe2—C11A—C15A−34.1 (19)C17—Fe2—C20—C1980.8 (6)
C12A—Fe2—C11A—C15A−114.6 (19)C14B—Fe2—C20—C19−105.1 (11)
C15A—C11A—C12A—C13A−1(3)C12A—Fe2—C20—C19−25 (3)
Fe2—C11A—C12A—C13A−58.2 (17)C15A—Fe2—C20—C29−16.5 (12)
C15A—C11A—C12A—Fe256.7 (18)C14A—Fe2—C20—C2927.8 (11)
C15A—Fe2—C12A—C13A81.4 (13)C13B—Fe2—C20—C2954.4 (17)
C14A—Fe2—C12A—C13A37.0 (14)C16—Fe2—C20—C29−115.0 (9)
C12B—Fe2—C12A—C13A130 (3)C11A—Fe2—C20—C29−58.6 (17)
C13B—Fe2—C12A—C13A25 (2)C19—Fe2—C20—C29126.9 (9)
C20—Fe2—C12A—C13A−43 (3)C11B—Fe2—C20—C29−57.7 (12)
C16—Fe2—C12A—C13A−171.9 (14)C17—Fe2—C20—C29−152.3 (8)
C11A—Fe2—C12A—C13A124.1 (18)C14B—Fe2—C20—C2921.8 (12)
C19—Fe2—C12A—C13A−62.6 (14)C12A—Fe2—C20—C29102 (3)
C11B—Fe2—C12A—C13A120.1 (17)C15A—Fe2—C20—C1698.5 (10)
C17—Fe2—C12A—C13A−142.6 (12)C14A—Fe2—C20—C16142.8 (10)
C14B—Fe2—C12A—C13A43.6 (19)C13B—Fe2—C20—C16169.4 (15)
C15A—Fe2—C12A—C11A−42.7 (12)C11A—Fe2—C20—C1656.4 (16)
C14A—Fe2—C12A—C11A−87.1 (15)C19—Fe2—C20—C16−118.1 (7)
C12B—Fe2—C12A—C11A6(2)C11B—Fe2—C20—C1657.3 (11)
C13B—Fe2—C12A—C11A−99 (3)C17—Fe2—C20—C16−37.3 (6)
C20—Fe2—C12A—C11A−166.7 (19)C14B—Fe2—C20—C16136.8 (11)
C16—Fe2—C12A—C11A64.0 (19)C12A—Fe2—C20—C16−143 (2)
C19—Fe2—C12A—C11A173.3 (11)N2—N1—C21—C103.1 (11)
C11B—Fe2—C12A—C11A−4.0 (13)Zn1—N1—C21—C10−161.6 (6)
C17—Fe2—C12A—C11A93.3 (13)C9—C10—C21—N1−176.8 (8)
C14B—Fe2—C12A—C11A−80.5 (19)C6—C10—C21—N15.2 (13)
C11A—C12A—C13A—C14A1(4)Fe1—C10—C21—N1−89.2 (10)
Fe2—C12A—C13A—C14A−56 (3)N1—N2—C22—N3−177.5 (6)
C11A—C12A—C13A—Fe256.8 (16)N1—N2—C22—S14.1 (9)
C15A—Fe2—C13A—C12A−83.2 (14)C23—N3—C22—N211.5 (11)
C14A—Fe2—C13A—C12A−121 (3)C23—N3—C22—S1−169.8 (6)
C12B—Fe2—C13A—C12A−20.5 (11)Zn1—S1—C22—N2−4.8 (7)
C13B—Fe2—C13A—C12A−43 (4)Zn1—S1—C22—N3176.7 (5)
C20—Fe2—C13A—C12A166.9 (10)C22—N3—C23—C24−161.8 (8)
C11A—Fe2—C13A—C12A−35.5 (12)C22—N3—C23—C2823.6 (11)
C19—Fe2—C13A—C12A132.2 (12)C28—C23—C24—C250.1 (13)
C11B—Fe2—C13A—C12A−50.5 (14)N3—C23—C24—C25−174.7 (7)
C17—Fe2—C13A—C12A60.5 (19)C23—C24—C25—C261.2 (13)
C14B—Fe2—C13A—C12A−113 (3)C24—C25—C26—C27−1.8 (12)
C15A—Fe2—C13A—C14A38 (2)C25—C26—C27—C281.2 (13)
C12B—Fe2—C13A—C14A100 (2)C26—C27—C28—C230.1 (12)
C13B—Fe2—C13A—C14A78 (4)C24—C23—C28—C27−0.7 (11)
C20—Fe2—C13A—C14A−72 (2)N3—C23—C28—C27173.9 (7)
C11A—Fe2—C13A—C14A85 (2)N5—N4—C29—C200.5 (13)
C19—Fe2—C13A—C14A−107 (2)Zn1—N4—C29—C20−174.7 (7)
C11B—Fe2—C13A—C14A70 (2)C19—C20—C29—N4−13.2 (17)
C17—Fe2—C13A—C14A−179 (2)C16—C20—C29—N4169.6 (9)
C14B—Fe2—C13A—C14A8(4)Fe2—C20—C29—N4−105.6 (10)
C12A—Fe2—C13A—C14A121 (3)N4—N5—C30—N6−178.1 (6)
C12A—C13A—C14A—C15A0(5)N4—N5—C30—S24.2 (10)
Fe2—C13A—C14A—C15A−58 (4)C31—N6—C30—N53.3 (12)
C12A—C13A—C14A—Fe258 (2)C31—N6—C30—S2−178.7 (6)
C12B—Fe2—C14A—C15A61.4 (19)Zn1—S2—C30—N5−12.0 (7)
C13B—Fe2—C14A—C15A94 (3)Zn1—S2—C30—N6170.2 (5)
C20—Fe2—C14A—C15A−110.9 (17)C30—N6—C31—C36−148.8 (8)
C16—Fe2—C14A—C15A−73 (3)C30—N6—C31—C3232.7 (12)
C11A—Fe2—C14A—C15A41.1 (17)C36—C31—C32—C333.2 (12)
C19—Fe2—C14A—C15A−154.3 (15)N6—C31—C32—C33−178.4 (8)
C11B—Fe2—C14A—C15A17.9 (17)C31—C32—C33—C34−2.8 (12)
C14B—Fe2—C14A—C15A2(20)C32—C33—C34—C351.4 (14)
C12A—Fe2—C14A—C15A84.6 (19)C33—C34—C35—C36−0.4 (14)
C15A—Fe2—C14A—C13A−120 (3)C34—C35—C36—C310.8 (14)
C12B—Fe2—C14A—C13A−58.5 (19)C32—C31—C36—C35−2.1 (14)
C13B—Fe2—C14A—C13A−26.3 (14)N6—C31—C36—C35179.3 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···S1i0.852.613.238 (10)132
N3—H3B···O1Wii0.862.142.981 (10)165
N6—H6B···O1W0.862.122.927 (11)155
C18—H18A···N2iii0.982.603.455 (10)146
O1W—H1W1···Cg1iv0.852.633.164 (9)123
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y+1/2, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···S1i0.852.613.238 (10)132
N3—H3B···O1Wii0.862.142.981 (10)165
N6—H6B···O1W0.862.122.927 (11)155
C18—H18A···N2iii0.982.603.455 (10)146
O1W—H1W1···Cg1iv0.852.633.164 (9)123
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y+1/2, −z.
Acknowledgements top

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.

references
References top

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