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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m967–m968.
Published online 2009 July 22. doi:  10.1107/S1600536809028104
PMCID: PMC2977240

(Cryptand-222)potassium(+) (hydrogensulfido)[5,10,15,20-tetra­kis(2-pival­amido­phen­yl)porphyrinato]ferrate(II)

Abstract

As part of a systematic investigation for a number of FeII porphyrin complexes used as biomimetic models for cytochrome P450, crystals of the title compound, [K(C18H36N2O6)][FeII(C64H64N8O4)(HS)], were prepared. The compound exhibits a non-planar conformation with major ruffling and saddling distortions. The average equatorial iron–pyrrole N atom [Fe—Np = 2.102 (2) Å] bond length and the distance between the FeII atom and the 24-atom core of the porphyrin ring (Fe—PC= 0.558 Å) are typical for high-spin iron(II) penta­coordinate porphyrinates. One of the tert-butyl groups in the structure is disordered over two sets with occupancies of 0.84 and 0.16.

Related literature

For general background to iron(II) porphyrin species and their applications, see: Simonneux & Le Maux (2000 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]). For the synthesis of iron(II) picket fence derivatives, see: Collman et al. (1975 [triangle]); Nasri et al. (1987 [triangle]); Hachem et al. (2009 [triangle]). For related structures, see: English et al. (1984 [triangle]); Nasri et al. (2000 [triangle]). For further details of geometric distortions in related compounds, see: Scheidt & Reed (1981 [triangle]); Scheidt (2000 [triangle]); Hu et al. (2005 [triangle]); Jentzen et al. (1997 [triangle]). For comparitive bond lengths, see: Allen et al. (1987 [triangle]). For the treatment of disordered solvent of crystallization, see: Spek (2009 [triangle]); Stähler et al. (2001 [triangle]); Cox et al. (2003 [triangle]); Mohamed et al. (2003 [triangle]); Athimoolam et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m967-scheme1.jpg

Experimental

Crystal data

  • [K(C18H36N2O6)][Fe(C64H64N8O4)(HS)]
  • M r = 1513.74
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m967-efi1.jpg
  • a = 17.9327 (7) Å
  • b = 21.5340 (7) Å
  • c = 22.7670 (9) Å
  • β = 100.611 (2)°
  • V = 8641.4 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 180 K
  • 0.25 × 0.24 × 0.21 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.842, T max = 0.937
  • 144342 measured reflections
  • 12322 independent reflections
  • 10135 reflections with I > 2σ(I)
  • R int = 0.048
  • θmax = 23.2°

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.128
  • S = 1.05
  • 12322 reflections
  • 965 parameters
  • 9 restraints
  • H-atom parameters constrained
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]) and ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028104/bg2280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028104/bg2280Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support from the Ministry of Higher Education, Scientific Research and Technology of Tunisia.

supplementary crystallographic information

Comment

A large number of iron-thiolate porphyrin complexes have been investigated in order to get more insight into the nature of the electronic and steriochemical properties of cytochromes P450 (Simonneux & Le Maux, 2000). In the Cambridge Structural Database (CSD, Version 5.30 of November 2008; Allen, 2002) there are only three structures of iron(II)-thiolate porphyrinates but no structure of hydrosulfido (SH-) iron(II) porphyrinate derivative is reported up to date. We report here the molecular structure of the iron(II) picket fence porphyrin (TpivPP) hydrosulfido species. In the structure of (I), the Fe2+ cation is coordinated to the sulfur atom of the SH- axial ligand from the pocket side of the TpivPP porphyrin (Fig. 1). The porphinato core undergoes a significant radial expansion in order to accommodate the high-spin Fe2+ cation. This is illustrated by the long Fe—Np and Fe—PC distances shown by these iron(II) high-spin [FeII(Porph)(X)]- complexes (X = anionic monodentate ligand). The average equatorial Fe—Np distance in (I) [2.102 (2) Å], which is longer than the corresponding Fe3+ species [FeIII(TAP)(SH)] (English et al., 1984) (TAP = tetrakis(p-methoxyphenyl)porphyrinate(2-) [2.015 (2) Å], falls within the range found for five-coordinate high-spin iron(II) porphyrins [2.072- 2.116 Å] (Scheidt & Reed, 1981; Scheidt, 2000; Hu et al., 2005). This is a stereochemical proof that compound (I) is high-spin (S = 2). The Fe—P~C distance [0.7578 Å] is quite longer than those of iron(II) high-spin five-coordinate porphyrines [0.50 – 0.64 Å]. For our model, the axial Fe—S(SH) bond length [2.312 (1) Å] is slightly shorter than those of the three iron(II)-thiolate porphyrinates cited in the literature [2.325 – 2.367 Å]. This distance is longer than the one of the [FeIII(TAP)(SH)] derivative [2.298 (3) Å]. It is noteworthy that Fe—SH distance for compound (I) is shorter than the Fe—S(thiole) bond length found for iron(II) thiole porphyrin species, i.e. for the ion complex [FeII(TpivPP)(NO2)(PMS)]- (Nasri et al., 2000) where PMS = pentamethylene sulfide) the Fe—S(PMS) distance is 2.380 (4) Å. The structural decomposition method [NSD] (Jentzen et al., 1997) indicates an important ruffling [41%], a quite high saddling [21%] and a moderate doming [14%] of the porphinato core. The negative charge of the [FeII(TpivPP)(SH)]- anion is balanced by a [K(2,2,2-crypt)]+ counterion. The average K—O(2,2,2-crypt) and K—N(2,2,2-crypt) distances [2.827 (2) Å and 3.035 (3) Å respectively] are in agreement with the literature values (Allen et al., 1987). There are no intermolecular or intermolecular hydrogen bonds in the structure of (I). The packing diagram for (I) (Fig.2) is simple. There is no evidence for intermolecular π -π bonding between the faces of the porphyrin cores in compound (I). The absence of the π -π interactions results mainly in the steric restrictions requirements of the pivalamide groups that determine the packing environment.

Experimental

The reaction sequence leading to the formation of compound (I) is not full understood at present. When a chlorobenzene solution of [FeII(TpivPP)] (Hachem et al., 2009), made in situ, is mixed under argon with excess of cryptand-222 and potassium thioacetate (C2H3OSK) a red-greenish solution was formed. Crystals of (I) were grown by diffusion of hexanes through the chlorobenzene solution.

Refinement

Due to the diffraction limitation of the crystals of (I) (at 180 K), the data collection was limited to 23.22° in θ. Hydrogen atoms were calculated at idealized positions and were refined with 1.2 times the isotropic displacement parameter of the corresponding carbon and nitrogen atoms. The H atom pertaining to the hydrosulfido ligand could not be found in a difference Fourier and was not included in the model.

The tert-butyl group of one picket is disordered over two sets. The occupancies of these two positions were refined and then fixed as 0.84 for C62/C63/C64 and 0.16 for C62A/C63A/C64A. The EADP commands in the SHELXL97 (Sheldrick, 2008) software were used to restrain the parameters of the disordered groups. Some anisotropic displacement ellipsoids of another tert-butyl group were rather elongated. This is the case of the anisotropic displacements U22 and U33 of the C29 and C31 carbons of the same tert-butyl group.These parameters were restrained to be the same than those of the third CH3 group (C30) of the same picket which presents normal ansisotropic displacements for such type of carbon moiety.

At the final stage of refinement, clear evidence of the presence of solvent voids of 241 Å3 was obtained (containing approximately 84 electrons). Several trials to find a reasonable model for this were unfruitful. Thus, a correction for diffuse effects due to the inclusion of disordered solvent molecules in the crystal structure was made using the SQUEEZE option in the program PLATON (Spek, 2009). The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2009). Similar treatments of disordered solvent molecules have been carried out in this manner (Stähler et al. (2001); Cox et al. (2003); Mohamed et al. (2003); Athimoolam et al. (2005).

Figures

Fig. 1.
A view of the structure of ion complex [FeII(TpivPP)(SH)]- and the [K(2,2,2,-crypt)]+ counterion showing the atom numbering schem. Displacement ellipsoids are drawn at 50%. The H atoms and the minor disorder tert-butyl group has been omitted for clarity. ...
Fig. 2.
A drawing showing the packing in (I), viewed down the b axis.

Crystal data

[K(C18H36N2O6)][Fe(C64H64N8O4)(HS)]F(000) = 3216
Mr = 1513.74Dx = 1.164 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9881 reflections
a = 17.9327 (7) Åθ = 2.6–23.9°
b = 21.5340 (7) ŵ = 0.31 mm1
c = 22.7670 (9) ÅT = 180 K
β = 100.611 (2)°Prism, dark purple
V = 8641.4 (6) Å30.25 × 0.24 × 0.21 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer12322 independent reflections
Radiation source: fine-focus sealed tube10135 reflections with I > 2σ(I)
graphiteRint = 0.048
[var phi] and ω scansθmax = 23.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −17→19
Tmin = 0.842, Tmax = 0.937k = −23→22
144342 measured reflectionsl = −25→25

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0663P)2 + 5.9377P] where P = (Fo2 + 2Fc2)/3
12322 reflections(Δ/σ)max = 0.048
965 parametersΔρmax = 0.58 e Å3
9 restraintsΔρmin = −0.45 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)
Fe0.042199 (18)0.071342 (15)0.229070 (15)0.02035 (11)
K0.24658 (3)0.14983 (3)0.04404 (3)0.03328 (16)
S0.00525 (5)0.04132 (4)0.31693 (3)0.0438 (2)
O10.35902 (15)−0.05101 (13)0.44571 (15)0.0879 (10)
O2−0.00865 (15)0.30157 (11)0.44698 (11)0.0663 (7)
O3−0.38816 (13)0.07683 (15)0.18152 (12)0.0819 (9)
O4−0.10604 (18)−0.25034 (13)0.24074 (15)0.0954 (11)
O50.17791 (11)0.21220 (9)−0.06246 (9)0.0422 (5)
O60.30993 (11)0.14053 (10)−0.05905 (9)0.0468 (5)
O70.23261 (11)0.01974 (9)0.05618 (8)0.0381 (5)
O80.11064 (11)0.10019 (10)0.06719 (10)0.0475 (5)
O90.26318 (11)0.25534 (9)0.12075 (8)0.0413 (5)
O100.38436 (10)0.17024 (8)0.12576 (9)0.0359 (5)
N10.12768 (11)0.00670 (9)0.22448 (9)0.0227 (5)
N20.12981 (11)0.13726 (9)0.25363 (9)0.0249 (5)
N3−0.02512 (12)0.14767 (9)0.19543 (10)0.0269 (5)
N4−0.02802 (11)0.01795 (9)0.16376 (9)0.0236 (5)
N50.29610 (13)0.02326 (11)0.38752 (10)0.0374 (6)
HN50.25350.04460.38100.045*
N60.01197 (18)0.25758 (12)0.36235 (12)0.0554 (8)
HN60.01540.22130.34530.067*
N7−0.26586 (13)0.08270 (12)0.16940 (11)0.0416 (6)
HN7−0.21930.07530.18820.050*
N8−0.02707 (13)−0.17059 (10)0.23845 (10)0.0357 (6)
HN8−0.0134−0.13410.25430.043*
N90.11215 (14)0.23331 (12)0.04717 (11)0.0453 (6)
N100.38315 (12)0.06590 (10)0.04173 (10)0.0341 (5)
C10.11518 (14)−0.05461 (11)0.20873 (11)0.0230 (6)
C20.18483 (15)−0.08910 (12)0.22589 (11)0.0290 (6)
H20.1913−0.13240.22080.035*
C30.23912 (15)−0.04840 (12)0.25046 (12)0.0292 (6)
H30.2910−0.05750.26540.035*
C40.20305 (14)0.01169 (11)0.24964 (11)0.0241 (6)
C50.23965 (14)0.06684 (12)0.27127 (11)0.0250 (6)
C60.20471 (14)0.12472 (12)0.27393 (11)0.0260 (6)
C70.24232 (15)0.17981 (12)0.30131 (12)0.0320 (6)
H70.29460.18360.31840.038*
C80.18931 (15)0.22458 (12)0.29799 (12)0.0331 (7)
H80.19690.26570.31290.040*
C90.11896 (14)0.19838 (11)0.26752 (11)0.0264 (6)
C100.05056 (15)0.23077 (12)0.25186 (12)0.0281 (6)
C11−0.01628 (15)0.20707 (12)0.21737 (12)0.0303 (6)
C12−0.08348 (16)0.24277 (13)0.19642 (15)0.0433 (8)
H12−0.09210.28470.20620.052*
C13−0.13204 (16)0.20557 (13)0.16026 (15)0.0449 (8)
H13−0.18090.21660.13910.054*
C14−0.09595 (14)0.14579 (12)0.15975 (12)0.0304 (6)
C15−0.12845 (14)0.09360 (12)0.12770 (12)0.0283 (6)
C16−0.09700 (13)0.03408 (11)0.13037 (11)0.0246 (6)
C17−0.13244 (15)−0.01987 (12)0.09970 (12)0.0298 (6)
H17−0.1802−0.02120.07350.036*
C18−0.08482 (15)−0.06829 (12)0.11526 (12)0.0292 (6)
H18−0.0932−0.11010.10250.035*
C19−0.01910 (14)−0.04436 (11)0.15478 (11)0.0240 (6)
C200.04683 (14)−0.07882 (11)0.17727 (11)0.0237 (6)
C210.32344 (14)0.06323 (11)0.29518 (12)0.0260 (6)
C220.37551 (15)0.08190 (12)0.26052 (13)0.0308 (6)
H220.35780.09770.22150.037*
C230.45264 (15)0.07790 (12)0.28170 (14)0.0357 (7)
H230.48760.09050.25740.043*
C240.47844 (15)0.05530 (13)0.33885 (14)0.0378 (7)
H240.53140.05240.35370.045*
C250.42799 (15)0.03695 (13)0.37424 (13)0.0360 (7)
H250.44630.02190.41350.043*
C260.35034 (15)0.04034 (12)0.35277 (12)0.0308 (6)
C270.30111 (17)−0.02178 (14)0.42973 (14)0.0442 (8)
C280.2289 (2)−0.03436 (15)0.45455 (15)0.0511 (8)
C290.2517 (3)−0.0560 (2)0.5186 (2)0.0941 (13)
H29A0.2896−0.08920.52070.141*
H29B0.2070−0.07180.53290.141*
H29C0.2734−0.02110.54370.141*
C300.1771 (2)0.02138 (19)0.4526 (2)0.0719 (11)
H30A0.20570.05660.47260.108*
H30B0.13500.01130.47290.108*
H30C0.15700.03230.41090.108*
C310.1864 (3)−0.0861 (2)0.4166 (2)0.0855 (11)
H31A0.1708−0.07160.37540.128*
H31B0.1414−0.09770.43280.128*
H31C0.2197−0.12230.41720.128*
C320.04810 (15)0.29677 (12)0.27287 (13)0.0324 (7)
C330.06150 (16)0.34574 (13)0.23722 (15)0.0394 (7)
H330.07510.33750.19960.047*
C340.05545 (17)0.40705 (14)0.25541 (16)0.0460 (8)
H340.06510.44040.23060.055*
C350.03542 (19)0.41843 (14)0.30961 (17)0.0515 (9)
H350.03030.46010.32190.062*
C360.02253 (19)0.37037 (15)0.34681 (16)0.0522 (9)
H360.00990.37910.38470.063*
C370.02810 (17)0.30929 (13)0.32848 (14)0.0405 (7)
C38−0.00786 (16)0.25520 (15)0.41683 (13)0.0410 (8)
C39−0.02581 (18)0.19145 (15)0.43781 (14)0.0454 (8)
C40−0.0543 (2)0.1989 (2)0.49710 (16)0.0730 (11)
H40A−0.01470.21840.52670.110*
H40B−0.06660.15800.51160.110*
H40C−0.09980.22510.49080.110*
C410.0468 (2)0.15148 (17)0.44790 (18)0.0649 (10)
H41A0.06410.14590.40990.097*
H41B0.03590.11080.46370.097*
H41C0.08640.17230.47650.097*
C42−0.08738 (19)0.15999 (16)0.39233 (16)0.0546 (9)
H42A−0.13210.18700.38390.082*
H42B−0.10140.12040.40860.082*
H42C−0.06830.15240.35530.082*
C43−0.20380 (15)0.10628 (12)0.08782 (13)0.0328 (7)
C44−0.20574 (18)0.12848 (14)0.03058 (13)0.0426 (7)
H44−0.16030.13010.01490.051*
C45−0.2733 (2)0.14838 (14)−0.00416 (15)0.0527 (9)
H45−0.27390.1640−0.04330.063*
C46−0.3394 (2)0.14545 (15)0.01823 (17)0.0555 (10)
H46−0.38560.1592−0.00550.067*
C47−0.33912 (17)0.12266 (15)0.07501 (15)0.0479 (8)
H47−0.38510.12050.09000.057*
C48−0.27131 (15)0.10290 (13)0.11028 (13)0.0364 (7)
C49−0.32059 (17)0.07264 (15)0.20256 (16)0.0484 (8)
C50−0.29353 (17)0.05719 (15)0.26818 (15)0.0465 (8)
C51−0.20843 (18)0.0463 (2)0.28585 (17)0.0646 (10)
H51A−0.19310.01310.26110.097*
H51B−0.19620.03410.32800.097*
H51C−0.18120.08450.27980.097*
C52−0.3360 (2)−0.00087 (18)0.2830 (2)0.0731 (11)
H52A−0.39080.00660.27310.110*
H52B−0.3214−0.01020.32570.110*
H52C−0.3229−0.03610.25960.110*
C53−0.3165 (2)0.11162 (18)0.30420 (17)0.0674 (10)
H53A−0.28820.14880.29670.101*
H53B−0.30510.10150.34690.101*
H53C−0.37100.11940.29210.101*
C540.04742 (14)−0.14673 (11)0.16275 (12)0.0264 (6)
C550.08766 (15)−0.16758 (12)0.12005 (12)0.0311 (6)
H550.1117−0.13800.09880.037*
C560.09408 (16)−0.22982 (13)0.10731 (13)0.0362 (7)
H560.1218−0.24280.07770.043*
C570.05944 (15)−0.27283 (12)0.13851 (13)0.0360 (7)
H570.0642−0.31590.13080.043*
C580.01841 (16)−0.25414 (12)0.18040 (13)0.0342 (7)
H58−0.0057−0.28420.20100.041*
C590.01175 (14)−0.19128 (12)0.19310 (12)0.0280 (6)
C60−0.08233 (19)−0.20026 (15)0.26013 (15)0.0465 (8)
C61−0.1158 (2)−0.16870 (16)0.30932 (16)0.0539 (9)
C62−0.1268 (3)−0.2177 (2)0.3550 (2)0.0813 (9)0.84
H62A−0.0777−0.23610.37220.122*0.84
H62B−0.1610−0.25010.33540.122*0.84
H62C−0.1490−0.19840.38680.122*0.84
C63−0.0624 (3)−0.1185 (3)0.3436 (2)0.0813 (9)0.84
H63A−0.0826−0.10480.37860.122*0.84
H63B−0.0593−0.08300.31720.122*0.84
H63C−0.0117−0.13620.35660.122*0.84
C64−0.1933 (3)−0.1425 (3)0.2813 (2)0.0813 (9)0.84
H64A−0.2248−0.17570.26020.122*0.84
H64B−0.1868−0.10960.25290.122*0.84
H64C−0.2180−0.12540.31270.122*0.84
C62A−0.0701 (13)−0.1780 (13)0.3665 (7)0.0813 (9)0.16
H62D−0.0323−0.14470.37460.122*0.16
H62E−0.0444−0.21820.36730.122*0.16
H62F−0.1022−0.17740.39700.122*0.16
C63A−0.1457 (16)−0.1036 (9)0.2853 (11)0.0813 (9)0.16
H63D−0.1841−0.08910.30770.122*0.16
H63E−0.1684−0.10690.24290.122*0.16
H63F−0.1035−0.07400.29040.122*0.16
C64A−0.1985 (10)−0.2025 (12)0.2985 (11)0.0813 (9)0.16
H64D−0.1918−0.24760.29870.122*0.16
H64E−0.2280−0.18940.25990.122*0.16
H64F−0.2256−0.19060.33050.122*0.16
C650.08101 (17)0.25233 (16)−0.01462 (15)0.0504 (8)
H65A0.04820.2891−0.01360.061*
H65B0.04890.2184−0.03480.061*
C660.14054 (18)0.26764 (15)−0.05033 (15)0.0495 (8)
H66A0.11700.2878−0.08830.059*
H66B0.17770.2969−0.02780.059*
C670.23079 (19)0.22303 (17)−0.10065 (15)0.0551 (9)
H67A0.27000.2527−0.08150.066*
H67B0.20440.2414−0.13870.066*
C680.26767 (19)0.16304 (17)−0.11297 (14)0.0529 (9)
H68A0.22850.1324−0.13000.063*
H68B0.30140.1699−0.14220.063*
C690.35155 (18)0.08645 (16)−0.06728 (14)0.0471 (8)
H69A0.37470.0910−0.10330.057*
H69B0.31730.0500−0.07300.057*
C700.41275 (17)0.07682 (15)−0.01301 (14)0.0436 (8)
H70A0.44430.0409−0.02020.052*
H70B0.44590.1139−0.00740.052*
C710.35853 (17)0.00097 (13)0.04389 (13)0.0387 (7)
H71A0.4034−0.02540.05820.046*
H71B0.3360−0.01280.00300.046*
C720.30177 (17)−0.00817 (13)0.08382 (13)0.0401 (7)
H72A0.2940−0.05310.09000.048*
H72B0.32030.01120.12320.048*
C730.17263 (18)0.00352 (15)0.08625 (15)0.0482 (8)
H73A0.18590.01590.12880.058*
H73B0.1649−0.04200.08460.058*
C740.10171 (18)0.03529 (16)0.05767 (15)0.0501 (9)
H74A0.09100.02630.01430.060*
H74B0.05850.02000.07520.060*
C750.04258 (18)0.13371 (17)0.04986 (17)0.0559 (9)
H75A0.00130.11370.06650.067*
H75B0.02800.13410.00580.067*
C760.05434 (19)0.19858 (18)0.07278 (18)0.0610 (10)
H76A0.00550.22120.06350.073*
H76B0.07000.19730.11680.073*
C770.13663 (19)0.28846 (16)0.08408 (16)0.0559 (9)
H77A0.09170.30730.09670.067*
H77B0.15770.31940.05940.067*
C780.19482 (19)0.27468 (17)0.13848 (15)0.0542 (9)
H78A0.20440.31230.16380.065*
H78B0.17610.24150.16210.065*
C790.32435 (17)0.25103 (15)0.16984 (13)0.0436 (8)
H79A0.31220.22030.19900.052*
H79B0.33270.29180.19010.052*
C800.39374 (16)0.23183 (14)0.14824 (14)0.0401 (7)
H80A0.40320.26030.11630.048*
H80B0.43790.23380.18140.048*
C810.45188 (16)0.14729 (13)0.10798 (15)0.0409 (7)
H81A0.49610.15390.14040.049*
H81B0.46100.16970.07200.049*
C820.44180 (16)0.07922 (13)0.09470 (14)0.0405 (7)
H82A0.49070.06170.08830.049*
H82B0.42800.05810.12980.049*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe0.01704 (19)0.0154 (2)0.0283 (2)−0.00017 (14)0.00341 (15)−0.00347 (14)
K0.0293 (3)0.0334 (4)0.0363 (3)−0.0034 (3)0.0036 (3)0.0028 (3)
S0.0485 (5)0.0474 (5)0.0400 (4)−0.0011 (4)0.0204 (4)−0.0003 (3)
O10.0568 (17)0.0754 (19)0.135 (3)0.0238 (15)0.0276 (17)0.0608 (19)
O20.0808 (18)0.0550 (15)0.0675 (16)−0.0020 (13)0.0252 (14)−0.0329 (13)
O30.0221 (13)0.138 (3)0.0820 (19)0.0016 (14)0.0007 (12)0.0137 (17)
O40.112 (2)0.0556 (18)0.141 (3)−0.0473 (17)0.083 (2)−0.0369 (18)
O50.0377 (12)0.0403 (12)0.0470 (12)−0.0046 (10)0.0035 (10)0.0119 (9)
O60.0394 (12)0.0632 (15)0.0381 (12)0.0054 (11)0.0077 (10)0.0104 (10)
O70.0401 (12)0.0375 (11)0.0389 (11)−0.0100 (9)0.0130 (9)0.0057 (9)
O80.0331 (12)0.0490 (14)0.0616 (14)−0.0078 (10)0.0120 (10)0.0029 (11)
O90.0397 (12)0.0452 (12)0.0368 (11)0.0075 (10)0.0014 (9)−0.0046 (9)
O100.0298 (10)0.0298 (11)0.0463 (12)−0.0031 (8)0.0023 (9)−0.0008 (9)
N10.0207 (11)0.0191 (12)0.0283 (11)−0.0018 (9)0.0046 (9)−0.0009 (9)
N20.0230 (12)0.0188 (12)0.0320 (12)0.0005 (9)0.0027 (9)−0.0023 (9)
N30.0236 (12)0.0189 (12)0.0372 (13)−0.0006 (9)0.0027 (10)−0.0044 (9)
N40.0220 (11)0.0183 (11)0.0307 (12)0.0012 (9)0.0054 (9)−0.0031 (9)
N50.0307 (13)0.0445 (15)0.0372 (13)0.0070 (11)0.0072 (11)0.0071 (11)
N60.090 (2)0.0294 (15)0.0535 (17)−0.0027 (14)0.0303 (16)−0.0174 (12)
N70.0185 (12)0.0541 (16)0.0495 (16)0.0050 (11)−0.0011 (11)−0.0054 (12)
N80.0442 (14)0.0206 (12)0.0445 (14)−0.0033 (11)0.0137 (12)−0.0002 (10)
N90.0373 (14)0.0464 (16)0.0503 (16)0.0062 (12)0.0031 (12)0.0006 (12)
N100.0276 (12)0.0309 (13)0.0435 (14)−0.0035 (10)0.0060 (11)0.0038 (10)
C10.0226 (14)0.0196 (14)0.0278 (14)−0.0014 (11)0.0074 (11)0.0004 (11)
C20.0312 (15)0.0203 (14)0.0352 (15)0.0030 (12)0.0055 (12)0.0017 (11)
C30.0236 (14)0.0259 (15)0.0365 (15)0.0027 (12)0.0012 (12)0.0002 (12)
C40.0233 (14)0.0224 (14)0.0266 (14)0.0007 (11)0.0044 (11)0.0010 (11)
C50.0223 (13)0.0265 (15)0.0260 (14)−0.0017 (11)0.0040 (11)−0.0004 (11)
C60.0234 (14)0.0234 (14)0.0304 (14)−0.0010 (11)0.0031 (11)0.0007 (11)
C70.0264 (15)0.0259 (15)0.0408 (16)−0.0037 (12)−0.0012 (12)−0.0038 (12)
C80.0327 (16)0.0224 (15)0.0422 (17)−0.0057 (13)0.0020 (13)−0.0089 (12)
C90.0280 (15)0.0216 (14)0.0295 (14)−0.0009 (11)0.0056 (11)−0.0024 (11)
C100.0299 (15)0.0191 (14)0.0361 (15)0.0004 (12)0.0085 (12)−0.0058 (11)
C110.0278 (15)0.0217 (15)0.0405 (16)0.0005 (12)0.0042 (12)−0.0066 (12)
C120.0349 (17)0.0218 (15)0.069 (2)0.0075 (13)−0.0017 (15)−0.0131 (14)
C130.0281 (16)0.0302 (17)0.070 (2)0.0088 (13)−0.0089 (15)−0.0117 (15)
C140.0229 (14)0.0239 (15)0.0426 (16)0.0026 (12)0.0015 (12)−0.0045 (12)
C150.0224 (14)0.0272 (15)0.0347 (15)0.0001 (12)0.0035 (12)−0.0031 (12)
C160.0197 (13)0.0236 (15)0.0310 (14)−0.0022 (11)0.0064 (11)−0.0020 (11)
C170.0229 (14)0.0282 (15)0.0364 (15)−0.0027 (12)0.0005 (12)−0.0070 (12)
C180.0285 (15)0.0206 (14)0.0376 (15)−0.0036 (12)0.0040 (12)−0.0069 (12)
C190.0237 (14)0.0206 (14)0.0286 (14)−0.0035 (11)0.0073 (11)−0.0003 (11)
C200.0246 (14)0.0179 (13)0.0292 (14)−0.0014 (11)0.0065 (11)−0.0005 (11)
C210.0231 (14)0.0167 (13)0.0373 (15)0.0009 (11)0.0034 (12)−0.0031 (11)
C220.0279 (15)0.0236 (15)0.0402 (16)−0.0021 (12)0.0047 (12)−0.0021 (12)
C230.0265 (16)0.0268 (16)0.0554 (19)−0.0025 (12)0.0112 (14)−0.0032 (13)
C240.0191 (14)0.0331 (16)0.058 (2)−0.0006 (12)−0.0002 (14)−0.0050 (14)
C250.0306 (16)0.0340 (16)0.0399 (16)0.0034 (13)−0.0028 (13)0.0003 (13)
C260.0295 (15)0.0260 (15)0.0366 (16)0.0014 (12)0.0051 (13)−0.0021 (12)
C270.0391 (18)0.0358 (17)0.058 (2)0.0070 (15)0.0095 (15)0.0110 (15)
C280.058 (2)0.045 (2)0.054 (2)0.0021 (17)0.0192 (17)0.0142 (16)
C290.129 (4)0.0700.0920.027 (3)0.044 (3)0.037 (2)
C300.065 (2)0.070 (3)0.091 (3)0.011 (2)0.041 (2)0.022 (2)
C310.103 (3)0.0700.092−0.032 (2)0.039 (3)−0.017 (2)
C320.0243 (14)0.0227 (15)0.0475 (17)0.0019 (12)−0.0004 (12)−0.0086 (13)
C330.0349 (16)0.0241 (16)0.058 (2)−0.0007 (13)0.0056 (14)−0.0039 (14)
C340.0384 (18)0.0236 (16)0.072 (2)−0.0032 (13)−0.0015 (16)−0.0044 (15)
C350.048 (2)0.0244 (17)0.078 (3)0.0039 (14)0.0018 (18)−0.0190 (17)
C360.060 (2)0.0347 (19)0.063 (2)0.0000 (16)0.0127 (17)−0.0220 (17)
C370.0410 (17)0.0284 (17)0.0508 (19)−0.0020 (13)0.0055 (14)−0.0133 (14)
C380.0303 (16)0.047 (2)0.0444 (18)0.0055 (14)0.0047 (14)−0.0183 (15)
C390.0434 (18)0.051 (2)0.0429 (18)−0.0002 (15)0.0113 (14)−0.0109 (15)
C400.089 (3)0.084 (3)0.053 (2)−0.005 (2)0.028 (2)−0.012 (2)
C410.059 (2)0.059 (2)0.072 (3)0.0127 (19)0.0016 (19)0.0052 (19)
C420.050 (2)0.055 (2)0.062 (2)−0.0098 (17)0.0176 (17)−0.0183 (17)
C430.0290 (15)0.0209 (15)0.0449 (17)0.0026 (12)−0.0028 (13)−0.0075 (12)
C440.0448 (19)0.0342 (17)0.0443 (18)0.0010 (14)−0.0036 (15)−0.0031 (14)
C450.063 (2)0.0356 (18)0.050 (2)0.0066 (17)−0.0154 (18)0.0010 (15)
C460.049 (2)0.0381 (19)0.066 (2)0.0114 (16)−0.0240 (18)−0.0083 (17)
C470.0306 (17)0.0455 (19)0.062 (2)0.0097 (14)−0.0064 (15)−0.0137 (16)
C480.0276 (16)0.0302 (16)0.0472 (18)0.0038 (12)−0.0039 (13)−0.0122 (13)
C490.0242 (18)0.051 (2)0.068 (2)−0.0001 (14)0.0042 (16)−0.0089 (17)
C500.0284 (16)0.052 (2)0.060 (2)0.0016 (14)0.0097 (15)0.0012 (16)
C510.0372 (19)0.097 (3)0.058 (2)0.0068 (19)0.0047 (16)0.012 (2)
C520.052 (2)0.059 (2)0.110 (3)−0.0007 (19)0.020 (2)0.009 (2)
C530.075 (3)0.063 (2)0.066 (2)0.009 (2)0.018 (2)−0.0035 (19)
C540.0214 (13)0.0196 (14)0.0354 (15)0.0000 (11)−0.0018 (12)−0.0002 (11)
C550.0271 (15)0.0257 (15)0.0402 (16)−0.0027 (12)0.0053 (12)−0.0039 (12)
C560.0332 (16)0.0272 (16)0.0478 (18)0.0042 (13)0.0062 (13)−0.0094 (13)
C570.0332 (16)0.0178 (14)0.0523 (18)0.0050 (12)−0.0040 (14)−0.0042 (13)
C580.0360 (16)0.0190 (15)0.0440 (17)−0.0003 (12)−0.0019 (13)0.0046 (12)
C590.0250 (14)0.0230 (15)0.0333 (15)0.0003 (11)−0.0014 (12)0.0006 (11)
C600.054 (2)0.0323 (19)0.058 (2)−0.0016 (16)0.0210 (17)0.0100 (15)
C610.064 (2)0.045 (2)0.060 (2)0.0131 (17)0.0294 (18)0.0136 (16)
C620.104 (2)0.081 (2)0.0676 (18)0.0104 (18)0.0387 (17)0.0036 (16)
C630.104 (2)0.081 (2)0.0676 (18)0.0104 (18)0.0387 (17)0.0036 (16)
C640.104 (2)0.081 (2)0.0676 (18)0.0104 (18)0.0387 (17)0.0036 (16)
C62A0.104 (2)0.081 (2)0.0676 (18)0.0104 (18)0.0387 (17)0.0036 (16)
C63A0.104 (2)0.081 (2)0.0676 (18)0.0104 (18)0.0387 (17)0.0036 (16)
C64A0.104 (2)0.081 (2)0.0676 (18)0.0104 (18)0.0387 (17)0.0036 (16)
C650.0354 (18)0.051 (2)0.059 (2)0.0097 (15)−0.0065 (15)0.0035 (16)
C660.0473 (19)0.0405 (19)0.053 (2)−0.0019 (16)−0.0111 (16)0.0119 (15)
C670.047 (2)0.062 (2)0.054 (2)−0.0092 (18)0.0060 (16)0.0286 (17)
C680.0452 (19)0.076 (3)0.0386 (18)−0.0037 (18)0.0109 (15)0.0184 (17)
C690.0448 (19)0.056 (2)0.0444 (18)−0.0059 (16)0.0184 (15)0.0014 (15)
C700.0325 (17)0.0466 (19)0.0537 (19)−0.0012 (14)0.0133 (14)0.0065 (15)
C710.0441 (18)0.0269 (15)0.0442 (17)−0.0032 (13)0.0058 (14)−0.0008 (13)
C720.0511 (19)0.0268 (16)0.0412 (17)−0.0066 (14)0.0050 (15)0.0031 (13)
C730.056 (2)0.0424 (19)0.0526 (19)−0.0136 (16)0.0281 (17)0.0075 (15)
C740.0439 (19)0.059 (2)0.052 (2)−0.0235 (17)0.0217 (16)−0.0028 (16)
C750.0327 (18)0.066 (2)0.070 (2)−0.0063 (17)0.0125 (16)0.0089 (19)
C760.0387 (19)0.075 (3)0.073 (2)0.0097 (18)0.0201 (18)0.004 (2)
C770.047 (2)0.054 (2)0.063 (2)0.0179 (17)0.0031 (17)−0.0108 (17)
C780.050 (2)0.062 (2)0.050 (2)0.0131 (17)0.0098 (16)−0.0108 (17)
C790.0476 (19)0.0465 (19)0.0340 (16)0.0014 (15)0.0003 (14)−0.0049 (14)
C800.0374 (17)0.0359 (17)0.0440 (17)−0.0052 (14)0.0000 (14)−0.0067 (13)
C810.0258 (15)0.0361 (17)0.058 (2)0.0001 (13)−0.0002 (14)0.0008 (14)
C820.0293 (16)0.0355 (17)0.0530 (19)0.0041 (13)−0.0024 (14)0.0035 (14)

Geometric parameters (Å, °)

Fe—N12.087 (2)C36—C371.389 (4)
Fe—N32.099 (2)C36—H360.9500
Fe—N42.104 (2)C38—C391.508 (5)
Fe—N22.115 (2)C39—C421.526 (4)
Fe—S2.3123 (8)C39—C401.537 (5)
K—O62.797 (2)C39—C411.542 (5)
K—O82.799 (2)C40—H40A0.9800
K—O72.831 (2)C40—H40B0.9800
K—O102.8402 (19)C40—H40C0.9800
K—O52.846 (2)C41—H41A0.9800
K—O92.848 (2)C41—H41B0.9800
K—N93.018 (3)C41—H41C0.9800
K—N103.052 (2)C42—H42A0.9800
O1—C271.212 (4)C42—H42B0.9800
O2—C381.213 (4)C42—H42C0.9800
O3—C491.221 (4)C43—C441.383 (4)
O4—C601.212 (4)C43—C481.400 (4)
O5—C671.419 (4)C44—C451.387 (4)
O5—C661.421 (4)C44—H440.9500
O6—C681.405 (4)C45—C461.375 (5)
O6—C691.414 (4)C45—H450.9500
O7—C721.417 (3)C46—C471.382 (5)
O7—C731.421 (3)C46—H460.9500
O8—C751.410 (4)C47—C481.395 (4)
O8—C741.419 (4)C47—H470.9500
O9—C791.418 (3)C49—C501.520 (5)
O9—C781.422 (4)C50—C511.523 (4)
O10—C801.420 (3)C50—C531.530 (5)
O10—C811.433 (3)C50—C521.533 (5)
N1—C41.372 (3)C51—H51A0.9800
N1—C11.376 (3)C51—H51B0.9800
N2—C61.365 (3)C51—H51C0.9800
N2—C91.376 (3)C52—H52A0.9800
N3—C111.372 (3)C52—H52B0.9800
N3—C141.376 (3)C52—H52C0.9800
N4—C191.371 (3)C53—H53A0.9800
N4—C161.372 (3)C53—H53B0.9800
N5—C271.357 (4)C53—H53C0.9800
N5—C261.411 (3)C54—C551.388 (4)
N5—HN50.8800C54—C591.403 (4)
N6—C381.353 (4)C55—C561.381 (4)
N6—C371.414 (4)C55—H550.9500
N6—HN60.8800C56—C571.382 (4)
N7—C491.361 (4)C56—H560.9500
N7—C481.401 (4)C57—C581.368 (4)
N7—HN70.8800C57—H570.9500
N8—C601.347 (4)C58—C591.394 (4)
N8—C591.419 (3)C58—H580.9500
N8—HN80.8800C60—C611.524 (5)
N9—C651.473 (4)C61—C62A1.418 (15)
N9—C771.474 (4)C61—C621.520 (6)
N9—C761.482 (4)C61—C641.527 (6)
N10—C701.461 (4)C61—C631.555 (6)
N10—C711.470 (4)C61—C63A1.563 (15)
N10—C821.475 (4)C61—C64A1.630 (16)
C1—C201.402 (4)C62—H62A0.9800
C1—C21.444 (4)C62—H62B0.9800
C2—C31.352 (4)C62—H62C0.9800
C2—H20.9500C63—H63A0.9800
C3—C41.445 (4)C63—H63B0.9800
C3—H30.9500C63—H63C0.9800
C4—C51.402 (4)C64—H64A0.9800
C5—C61.401 (4)C64—H64B0.9800
C5—C211.503 (4)C64—H64C0.9800
C6—C71.448 (4)C62A—H62D0.9800
C7—C81.346 (4)C62A—H62E0.9800
C7—H70.9500C62A—H62F0.9800
C8—C91.438 (4)C63A—H63D0.9800
C8—H80.9500C63A—H63E0.9800
C9—C101.399 (4)C63A—H63F0.9800
C10—C111.403 (4)C64A—H64D0.9800
C10—C321.503 (4)C64A—H64E0.9800
C11—C121.435 (4)C64A—H64F0.9800
C12—C131.347 (4)C65—C661.493 (5)
C12—H120.9500C65—H65A0.9900
C13—C141.442 (4)C65—H65B0.9900
C13—H130.9500C66—H66A0.9900
C14—C151.407 (4)C66—H66B0.9900
C15—C161.397 (4)C67—C681.501 (5)
C15—C431.508 (4)C67—H67A0.9900
C16—C171.441 (4)C67—H67B0.9900
C17—C181.353 (4)C68—H68A0.9900
C17—H170.9500C68—H68B0.9900
C18—C191.440 (4)C69—C701.508 (4)
C18—H180.9500C69—H69A0.9900
C19—C201.410 (4)C69—H69B0.9900
C20—C541.500 (3)C70—H70A0.9900
C21—C221.388 (4)C70—H70B0.9900
C21—C261.401 (4)C71—C721.497 (4)
C22—C231.381 (4)C71—H71A0.9900
C22—H220.9500C71—H71B0.9900
C23—C241.387 (4)C72—H72A0.9900
C23—H230.9500C72—H72B0.9900
C24—C251.375 (4)C73—C741.485 (5)
C24—H240.9500C73—H73A0.9900
C25—C261.390 (4)C73—H73B0.9900
C25—H250.9500C74—H74A0.9900
C27—C281.530 (4)C74—H74B0.9900
C28—C301.514 (5)C75—C761.493 (5)
C28—C291.514 (5)C75—H75A0.9900
C28—C311.525 (5)C75—H75B0.9900
C29—H29A0.9800C76—H76A0.9900
C29—H29B0.9800C76—H76B0.9900
C29—H29C0.9800C77—C781.495 (5)
C30—H30A0.9800C77—H77A0.9900
C30—H30B0.9800C77—H77B0.9900
C30—H30C0.9800C78—H78A0.9900
C31—H31A0.9800C78—H78B0.9900
C31—H31B0.9800C79—C801.479 (4)
C31—H31C0.9800C79—H79A0.9900
C32—C331.379 (4)C79—H79B0.9900
C32—C371.404 (4)C80—H80A0.9900
C33—C341.394 (4)C80—H80B0.9900
C33—H330.9500C81—C821.501 (4)
C34—C351.369 (5)C81—H81A0.9900
C34—H340.9500C81—H81B0.9900
C35—C361.383 (5)C82—H82A0.9900
C35—H350.9500C82—H82B0.9900
N1—Fe—N3151.92 (8)H41A—C41—H41B109.5
N1—Fe—N487.11 (8)C39—C41—H41C109.5
N3—Fe—N486.61 (8)H41A—C41—H41C109.5
N1—Fe—N286.80 (8)H41B—C41—H41C109.5
N3—Fe—N285.43 (8)C39—C42—H42A109.5
N4—Fe—N2150.72 (8)C39—C42—H42B109.5
N1—Fe—S100.78 (6)H42A—C42—H42B109.5
N3—Fe—S107.30 (6)C39—C42—H42C109.5
N4—Fe—S103.24 (6)H42A—C42—H42C109.5
N2—Fe—S106.03 (6)H42B—C42—H42C109.5
O6—K—O8129.28 (7)C44—C43—C48119.3 (3)
O6—K—O793.90 (6)C44—C43—C15119.6 (3)
O8—K—O760.52 (6)C48—C43—C15120.7 (3)
O6—K—O1097.01 (6)C43—C44—C45120.8 (3)
O8—K—O10128.20 (6)C43—C44—H44119.6
O7—K—O1099.85 (6)C45—C44—H44119.6
O6—K—O559.85 (6)C46—C45—C44119.8 (3)
O8—K—O594.90 (6)C46—C45—H45120.1
O7—K—O5121.20 (6)C44—C45—H45120.1
O10—K—O5132.29 (6)C45—C46—C47120.6 (3)
O6—K—O9123.99 (7)C45—C46—H46119.7
O8—K—O9100.69 (6)C47—C46—H46119.7
O7—K—O9136.96 (6)C46—C47—C48119.9 (3)
O10—K—O959.65 (5)C46—C47—H47120.0
O5—K—O997.23 (6)C48—C47—H47120.0
O6—K—N9120.80 (7)C47—C48—C43119.7 (3)
O8—K—N959.74 (7)C47—C48—N7123.2 (3)
O7—K—N9120.11 (7)C43—C48—N7117.1 (2)
O10—K—N9119.64 (6)O3—C49—N7122.4 (3)
O5—K—N961.11 (7)O3—C49—C50121.0 (3)
O9—K—N960.27 (6)N7—C49—C50116.6 (3)
O6—K—N1059.46 (6)C49—C50—C51114.6 (3)
O8—K—N10120.43 (6)C49—C50—C53106.9 (3)
O7—K—N1060.09 (6)C51—C50—C53109.4 (3)
O10—K—N1059.92 (6)C49—C50—C52108.2 (3)
O5—K—N10119.18 (6)C51—C50—C52109.3 (3)
O9—K—N10119.30 (6)C53—C50—C52108.2 (3)
N9—K—N10179.56 (7)C50—C51—H51A109.5
C67—O5—C66111.9 (2)C50—C51—H51B109.5
C67—O5—K111.50 (17)H51A—C51—H51B109.5
C66—O5—K112.12 (17)C50—C51—H51C109.5
C68—O6—C69112.4 (2)H51A—C51—H51C109.5
C68—O6—K118.13 (18)H51B—C51—H51C109.5
C69—O6—K118.42 (17)C50—C52—H52A109.5
C72—O7—C73111.1 (2)C50—C52—H52B109.5
C72—O7—K112.16 (15)H52A—C52—H52B109.5
C73—O7—K112.26 (17)C50—C52—H52C109.5
C75—O8—C74113.2 (2)H52A—C52—H52C109.5
C75—O8—K119.38 (18)H52B—C52—H52C109.5
C74—O8—K115.16 (16)C50—C53—H53A109.5
C79—O9—C78112.2 (2)C50—C53—H53B109.5
C79—O9—K114.18 (16)H53A—C53—H53B109.5
C78—O9—K114.18 (18)C50—C53—H53C109.5
C80—O10—C81111.9 (2)H53A—C53—H53C109.5
C80—O10—K114.30 (15)H53B—C53—H53C109.5
C81—O10—K116.10 (16)C55—C54—C59117.8 (2)
C4—N1—C1106.5 (2)C55—C54—C20119.7 (2)
C4—N1—Fe127.09 (16)C59—C54—C20122.4 (2)
C1—N1—Fe124.55 (16)C56—C55—C54122.4 (3)
C6—N2—C9106.5 (2)C56—C55—H55118.8
C6—N2—Fe126.43 (16)C54—C55—H55118.8
C9—N2—Fe124.98 (16)C55—C56—C57118.7 (3)
C11—N3—C14105.9 (2)C55—C56—H56120.7
C11—N3—Fe125.25 (17)C57—C56—H56120.7
C14—N3—Fe126.77 (16)C58—C57—C56120.8 (3)
C19—N4—C16106.4 (2)C58—C57—H57119.6
C19—N4—Fe124.68 (16)C56—C57—H57119.6
C16—N4—Fe127.90 (16)C57—C58—C59120.5 (3)
C27—N5—C26128.4 (2)C57—C58—H58119.7
C27—N5—HN5115.8C59—C58—H58119.7
C26—N5—HN5115.8C58—C59—C54119.8 (3)
C38—N6—C37130.1 (3)C58—C59—N8121.9 (2)
C38—N6—HN6114.9C54—C59—N8118.2 (2)
C37—N6—HN6114.9O4—C60—N8121.4 (3)
C49—N7—C48130.7 (2)O4—C60—C61120.4 (3)
C49—N7—HN7114.6N8—C60—C61118.3 (3)
C48—N7—HN7114.6C62A—C61—C6253.2 (11)
C60—N8—C59127.6 (2)C62A—C61—C60111.9 (10)
C60—N8—HN8116.2C62—C61—C60108.2 (3)
C59—N8—HN8116.2C62A—C61—C64139.7 (10)
C65—N9—C77109.9 (3)C62—C61—C64108.6 (4)
C65—N9—C76110.3 (3)C60—C61—C64108.0 (3)
C77—N9—C76109.8 (3)C62A—C61—C6355.9 (12)
C65—N9—K107.88 (18)C62—C61—C63106.5 (4)
C77—N9—K109.75 (18)C60—C61—C63112.9 (3)
C76—N9—K109.17 (19)C64—C61—C63112.5 (4)
C70—N10—C71109.9 (2)C62A—C61—C63A123.4 (15)
C70—N10—C82110.5 (2)C62—C61—C63A141.4 (9)
C71—N10—C82109.3 (2)C60—C61—C63A107.4 (9)
C70—N10—K109.76 (16)C64—C61—C63A45.2 (10)
C71—N10—K108.41 (16)C63—C61—C63A72.1 (11)
C82—N10—K108.92 (16)C62A—C61—C64A115.5 (14)
N1—C1—C20125.1 (2)C62—C61—C64A64.1 (9)
N1—C1—C2109.4 (2)C60—C61—C64A99.3 (9)
C20—C1—C2125.3 (2)C64—C61—C64A50.8 (9)
C3—C2—C1107.4 (2)C63—C61—C64A147.6 (9)
C3—C2—H2126.3C63A—C61—C64A95.9 (13)
C1—C2—H2126.3C61—C62—H62A109.5
C2—C3—C4106.8 (2)C61—C62—H62B109.5
C2—C3—H3126.6C61—C62—H62C109.5
C4—C3—H3126.6C61—C63—H63A109.5
N1—C4—C5125.1 (2)C61—C63—H63B109.5
N1—C4—C3109.9 (2)C61—C63—H63C109.5
C5—C4—C3125.1 (2)C61—C64—H64A109.5
C6—C5—C4125.8 (2)C61—C64—H64B109.5
C6—C5—C21117.1 (2)C61—C64—H64C109.5
C4—C5—C21117.1 (2)C61—C62A—H62D109.5
N2—C6—C5125.5 (2)C61—C62A—H62E109.5
N2—C6—C7109.6 (2)H62D—C62A—H62E109.5
C5—C6—C7124.8 (2)C61—C62A—H62F109.5
C8—C7—C6107.1 (2)H62D—C62A—H62F109.5
C8—C7—H7126.4H62E—C62A—H62F109.5
C6—C7—H7126.4C61—C63A—H63D109.5
C7—C8—C9107.1 (2)C61—C63A—H63E109.5
C7—C8—H8126.5H63D—C63A—H63E109.5
C9—C8—H8126.5C61—C63A—H63F109.5
N2—C9—C10124.9 (2)H63D—C63A—H63F109.5
N2—C9—C8109.7 (2)H63E—C63A—H63F109.5
C10—C9—C8125.3 (2)C61—C64A—H64D109.5
C9—C10—C11125.5 (2)C61—C64A—H64E109.5
C9—C10—C32117.8 (2)H64D—C64A—H64E109.5
C11—C10—C32116.8 (2)C61—C64A—H64F109.5
N3—C11—C10124.9 (2)H64D—C64A—H64F109.5
N3—C11—C12110.2 (2)H64E—C64A—H64F109.5
C10—C11—C12124.8 (2)N9—C65—C66113.5 (3)
C13—C12—C11107.1 (2)N9—C65—H65A108.9
C13—C12—H12126.5C66—C65—H65A108.9
C11—C12—H12126.5N9—C65—H65B108.9
C12—C13—C14107.2 (2)C66—C65—H65B108.9
C12—C13—H13126.4H65A—C65—H65B107.7
C14—C13—H13126.4O5—C66—C65109.3 (3)
N3—C14—C15125.4 (2)O5—C66—H66A109.8
N3—C14—C13109.6 (2)C65—C66—H66A109.8
C15—C14—C13125.0 (2)O5—C66—H66B109.8
C16—C15—C14125.8 (2)C65—C66—H66B109.8
C16—C15—C43120.1 (2)H66A—C66—H66B108.3
C14—C15—C43114.1 (2)O5—C67—C68109.9 (3)
N4—C16—C15124.9 (2)O5—C67—H67A109.7
N4—C16—C17109.7 (2)C68—C67—H67A109.7
C15—C16—C17125.4 (2)O5—C67—H67B109.7
C18—C17—C16107.1 (2)C68—C67—H67B109.7
C18—C17—H17126.5H67A—C67—H67B108.2
C16—C17—H17126.5O6—C68—C67108.6 (3)
C17—C18—C19107.0 (2)O6—C68—H68A110.0
C17—C18—H18126.5C67—C68—H68A110.0
C19—C18—H18126.5O6—C68—H68B110.0
N4—C19—C20125.0 (2)C67—C68—H68B110.0
N4—C19—C18109.8 (2)H68A—C68—H68B108.4
C20—C19—C18125.0 (2)O6—C69—C70109.1 (3)
C1—C20—C19125.9 (2)O6—C69—H69A109.9
C1—C20—C54115.7 (2)C70—C69—H69A109.9
C19—C20—C54118.2 (2)O6—C69—H69B109.9
C22—C21—C26118.8 (2)C70—C69—H69B109.9
C22—C21—C5120.8 (2)H69A—C69—H69B108.3
C26—C21—C5120.4 (2)N10—C70—C69113.4 (2)
C23—C22—C21121.2 (3)N10—C70—H70A108.9
C23—C22—H22119.4C69—C70—H70A108.9
C21—C22—H22119.4N10—C70—H70B108.9
C22—C23—C24119.3 (3)C69—C70—H70B108.9
C22—C23—H23120.4H70A—C70—H70B107.7
C24—C23—H23120.4N10—C71—C72112.8 (2)
C25—C24—C23120.6 (3)N10—C71—H71A109.0
C25—C24—H24119.7C72—C71—H71A109.0
C23—C24—H24119.7N10—C71—H71B109.0
C24—C25—C26120.2 (3)C72—C71—H71B109.0
C24—C25—H25119.9H71A—C71—H71B107.8
C26—C25—H25119.9O7—C72—C71108.2 (2)
C25—C26—C21119.8 (3)O7—C72—H72A110.1
C25—C26—N5122.6 (2)C71—C72—H72A110.1
C21—C26—N5117.5 (2)O7—C72—H72B110.1
O1—C27—N5121.7 (3)C71—C72—H72B110.1
O1—C27—C28122.3 (3)H72A—C72—H72B108.4
N5—C27—C28116.0 (3)O7—C73—C74109.8 (2)
C30—C28—C29109.2 (3)O7—C73—H73A109.7
C30—C28—C31108.8 (3)C74—C73—H73A109.7
C29—C28—C31109.8 (3)O7—C73—H73B109.7
C30—C28—C27113.9 (3)C74—C73—H73B109.7
C29—C28—C27108.2 (3)H73A—C73—H73B108.2
C31—C28—C27106.8 (3)O8—C74—C73108.9 (3)
C28—C29—H29A109.5O8—C74—H74A109.9
C28—C29—H29B109.5C73—C74—H74A109.9
H29A—C29—H29B109.5O8—C74—H74B109.9
C28—C29—H29C109.5C73—C74—H74B109.9
H29A—C29—H29C109.5H74A—C74—H74B108.3
H29B—C29—H29C109.5O8—C75—C76108.8 (3)
C28—C30—H30A109.5O8—C75—H75A109.9
C28—C30—H30B109.5C76—C75—H75A109.9
H30A—C30—H30B109.5O8—C75—H75B109.9
C28—C30—H30C109.5C76—C75—H75B109.9
H30A—C30—H30C109.5H75A—C75—H75B108.3
H30B—C30—H30C109.5N9—C76—C75113.5 (3)
C28—C31—H31A109.5N9—C76—H76A108.9
C28—C31—H31B109.5C75—C76—H76A108.9
H31A—C31—H31B109.5N9—C76—H76B108.9
C28—C31—H31C109.5C75—C76—H76B108.9
H31A—C31—H31C109.5H76A—C76—H76B107.7
H31B—C31—H31C109.5N9—C77—C78113.7 (3)
C33—C32—C37119.0 (3)N9—C77—H77A108.8
C33—C32—C10121.2 (3)C78—C77—H77A108.8
C37—C32—C10119.7 (3)N9—C77—H77B108.8
C32—C33—C34121.2 (3)C78—C77—H77B108.8
C32—C33—H33119.4H77A—C77—H77B107.7
C34—C33—H33119.4O9—C78—C77109.3 (3)
C35—C34—C33119.0 (3)O9—C78—H78A109.8
C35—C34—H34120.5C77—C78—H78A109.8
C33—C34—H34120.5O9—C78—H78B109.8
C34—C35—C36121.3 (3)C77—C78—H78B109.8
C34—C35—H35119.4H78A—C78—H78B108.3
C36—C35—H35119.4O9—C79—C80109.4 (2)
C35—C36—C37119.7 (3)O9—C79—H79A109.8
C35—C36—H36120.2C80—C79—H79A109.8
C37—C36—H36120.2O9—C79—H79B109.8
C36—C37—C32119.8 (3)C80—C79—H79B109.8
C36—C37—N6123.3 (3)H79A—C79—H79B108.2
C32—C37—N6116.9 (2)O10—C80—C79109.3 (2)
O2—C38—N6121.3 (3)O10—C80—H80A109.8
O2—C38—C39123.0 (3)C79—C80—H80A109.8
N6—C38—C39115.6 (3)O10—C80—H80B109.8
C38—C39—C42111.1 (3)C79—C80—H80B109.8
C38—C39—C40107.9 (3)H80A—C80—H80B108.3
C42—C39—C40109.0 (3)O10—C81—C82108.5 (2)
C38—C39—C41109.4 (3)O10—C81—H81A110.0
C42—C39—C41109.8 (3)C82—C81—H81A110.0
C40—C39—C41109.6 (3)O10—C81—H81B110.0
C39—C40—H40A109.5C82—C81—H81B110.0
C39—C40—H40B109.5H81A—C81—H81B108.4
H40A—C40—H40B109.5N10—C82—C81113.3 (2)
C39—C40—H40C109.5N10—C82—H82A108.9
H40A—C40—H40C109.5C81—C82—H82A108.9
H40B—C40—H40C109.5N10—C82—H82B108.9
C39—C41—H41A109.5C81—C82—H82B108.9
C39—C41—H41B109.5H82A—C82—H82B107.7

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2280).

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