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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1524–m1525.
Published online 2009 November 7. doi:  10.1107/S1600536809046078
PMCID: PMC2971859

Bis(1-ferrocenylmethyl­idene-4-phenyl­thiosemicarbazidato-κ2 N 1,S)zinc(II) monohydrate

Abstract

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(...)π inter­actions.

Related literature

For related structures, see: Vikneswaran et al. (2009a [triangle],b [triangle]). For the preparation, 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-65-m1524-scheme1.jpg

Experimental

Crystal data

  • [Fe2Zn(C5H5)2(C13H11N3S)2]·H2O
  • M r = 807.88
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1524-efi1.jpg
  • a = 10.4500 (5) Å
  • b = 10.4892 (5) Å
  • c = 15.9377 (7) Å
  • β = 104.277 (2)°
  • V = 1693.01 (14) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.71 mm−1
  • T = 100 K
  • 0.65 × 0.17 × 0.09 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.402, T max = 0.858
  • 17262 measured reflections
  • 7565 independent reflections
  • 5980 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.174
  • S = 1.09
  • 7565 reflections
  • 473 parameters
  • 163 restraints
  • H-atom parameters constrained
  • Δρmax = 2.43 e Å−3
  • Δρmin = −0.71 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3458 Friedel pairs
  • Flack parameter: 0.50 (2)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046078/ci2959sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046078/ci2959Isup2.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 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.

Experimental

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

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.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. All disorder components are shown.
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.

Crystal data

[Fe2Zn(C5H5)2(C13H11N3S)2]·H2OF(000) = 828
Mr = 807.88Dx = 1.585 Mg m3
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 mm1
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

Bruker SMART APEXII CCD area-detector diffractometer7565 independent reflections
Radiation source: fine-focus sealed tube5980 reflections with I > 2σ(I)
graphiteRint = 0.050
[var phi] 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

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) = 0.174w = 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 Å3
473 parametersΔρmin = −0.71 e Å3
163 restraintsAbsolute structure: Flack (1983), 3458 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.50 (2)

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2959).

References

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