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Treatment of the ortho-tri­aza­cyclo­phane 1,4-di­methyl­tribenzo[b,e,h][1,4,7]tri­aza­cyclo­nona-2,5,8-triene [(C6H5)3(NH)(NCH3)2, L1] with Fe[N(SiMe3)2]2 yields the dimeric iron(II) complex bis­(μ-1,4-di­methyl­tribenzo[b,e,h][1,4,7]tri­aza­cyclo­nona-2,5,8-trien-7-ido)bis­[(μ-1,4-di­methyl­tribenzo[b,e,h][1,4,7]tri­aza­cyclo­nona-2,5,8-trien-7-ido)iron(II)], [Fe(C20H18N3)4] or Fe2(L1)4 (9). Dissolution of 9 in tetra­hydro­furan (THF) results in solvation by two THF ligands and the formation of a simpler monoiron complex, namely bis­(μ-1,4-di­methyl­tribenzo[b,e,h][1,4,7]tri­aza­cyclo­nona-2,5,8-trien-7-ido-κN7)bis­(tetra­hydro­furan-κO)iron(II), [Fe(C20H18N3)2(C4H8O)2] or (L1)2Fe(THF)2 (10). The reaction is reversible and 10 reverts in vacuo to diiron complex 9. In the structures of both 9 and 10, the monoanionic tri­aza­cyclo­phane ligand L1 is observed in only the less-symmetric saddle conformation. No bowl-shaped crown conformers are observed in the solid state, thus preventing chelating κ3-coordination to the metal as had been proposed earlier based on density functional theory (DFT) calculations. Instead, the L1 ligands are bound in either a η2-chelating fashion through the amide and one amine donor (for one of the four ligands of 9), or solely through their amide N atoms in an even simpler monodentate η1-coordination mode. Density functional calculations on dimer 9 revealed nearly full cationic charges on each Fe atom and no bonding inter­action between the two metal centers, consistent with the relatively long Fe...Fe distance of 2.912 (1) Å observed in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015255/qs3077sup1.cif
Contains datablocks 9, 10, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015255/qs30779sup2.hkl
Contains datablock 9

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015255/qs307710sup3.hkl
Contains datablock 10

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618015255/qs3077sup4.pdf
Fully labelled ellipsoid plots

CCDC references: 1875771; 1875770

Computing details top

For both structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis(µ-1,4-dimethyltribenzo[b,e,h][1,4,7]triazacyclonona-2,5,8-trien-7-ido)-1:2κ2N1,N7:κN7; 1:2κN7:κ2N7,C6-bis[(µ-1,4-dimethyltribenzo[b,e,h][1,4,7]triazacyclonona-2,5,8-trien-7-ido-κN7)iron(II)] (9) top
Crystal data top
[Fe(C20H18N3)4]F(000) = 2752
Mr = 1313.19Dx = 1.059 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 21.758 (2) ÅCell parameters from 8887 reflections
b = 12.7682 (13) Åθ = 3.0–65.8°
c = 31.382 (3) ŵ = 3.17 mm1
β = 109.191 (5)°T = 100 K
V = 8233.7 (14) Å3Rod, red
Z = 40.11 × 0.06 × 0.05 mm
Data collection top
Bruker Prospector CCD
diffractometer
14191 independent reflections
Radiation source: I-mu-S microsource X-ray tube8827 reflections with I > 2σ(I)
Laterally graded multilayer (Goebel) mirror monochromatorRint = 0.133
ω and phi scansθmax = 66.9°, θmin = 2.2°
Absorption correction: multi-scan
(APEX2; Bruker, 2014)
h = 2525
Tmin = 0.478, Tmax = 0.753k = 1415
52565 measured reflectionsl = 2337
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0816P)2 + 5.4245P]
where P = (Fo2 + 2Fc2)/3
14191 reflections(Δ/σ)max < 0.001
855 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.54 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structure contains solvent accessible voids of 2479.0 Ang3 (30% of the unit cell volume). The the residual electron density peaks were not arranged in an interpretable pattern. The hkl file was thus corrected using reverse Fourier transform methods using the SQUEEZE routine (P. van der Sluis & Spek (1990). Acta Cryst. A46, 194-201) as implemented in the program Platon. The resultant files were used in the further refinement. (The FAB file with details of the Squeeze results is appended to this cif file). The Squeeze procedure corrected for 569.8 electrons within the solvent accesible voids, equivalent of eight molecules of tetrahydro furane (the crystallization solvent).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2847 (2)0.3704 (4)0.38404 (15)0.0336 (11)
C20.2243 (2)0.3887 (4)0.35057 (15)0.0339 (11)
H20.20970.34250.32550.041*
C30.1860 (2)0.4723 (4)0.35341 (17)0.0418 (13)
H30.14530.48260.33040.050*
C40.2056 (3)0.5413 (4)0.38898 (18)0.0509 (15)
H40.17840.59770.39140.061*
C50.2668 (2)0.5262 (4)0.42160 (17)0.0462 (14)
H50.28190.57470.44570.055*
C60.3053 (2)0.4428 (4)0.41940 (16)0.0367 (12)
C70.4093 (2)0.5186 (4)0.45291 (16)0.0395 (12)
C80.4367 (2)0.5861 (4)0.48879 (17)0.0457 (14)
H80.43170.57190.51720.055*
C90.4713 (3)0.6743 (4)0.48399 (19)0.0510 (15)
H90.49110.71860.50910.061*
C100.4768 (3)0.6969 (4)0.4424 (2)0.0552 (16)
H100.49710.76020.43830.066*
C110.4526 (2)0.6272 (4)0.40623 (18)0.0487 (14)
H110.45840.64210.37810.058*
C120.4198 (2)0.5352 (4)0.41123 (16)0.0398 (12)
C130.4224 (2)0.3570 (4)0.38532 (15)0.0364 (12)
C140.4872 (2)0.3433 (4)0.39039 (16)0.0413 (12)
H140.51360.40310.39150.050*
C150.5148 (3)0.2450 (4)0.39382 (17)0.0494 (14)
H150.55970.23670.39750.059*
C160.4750 (2)0.1579 (4)0.39176 (16)0.0446 (13)
H160.49250.08930.39320.053*
C170.4108 (2)0.1712 (4)0.38768 (15)0.0362 (11)
H170.38460.11090.38610.043*
C180.3823 (2)0.2705 (4)0.38573 (15)0.0336 (11)
C190.3620 (2)0.4097 (4)0.49871 (16)0.0444 (13)
H19A0.33480.34730.49660.067*
H19B0.34170.46970.50830.067*
H19C0.40520.39730.52080.067*
C200.3840 (3)0.4952 (4)0.33024 (16)0.0550 (15)
H20A0.35660.44340.30950.083*
H20B0.42570.50110.32490.083*
H20C0.36200.56330.32510.083*
C210.1671 (2)0.1208 (3)0.31601 (14)0.0284 (10)
C220.1206 (2)0.1744 (3)0.32995 (14)0.0285 (10)
H220.11410.15500.35740.034*
C230.0841 (2)0.2552 (3)0.30420 (15)0.0304 (10)
H230.05320.29090.31430.036*
C240.0924 (2)0.2842 (4)0.26395 (15)0.0334 (11)
H240.06620.33740.24570.040*
C250.1398 (2)0.2342 (4)0.25073 (15)0.0320 (11)
H250.14670.25550.22370.038*
C260.1770 (2)0.1544 (4)0.27575 (14)0.0313 (11)
C270.2018 (2)0.0586 (4)0.21864 (15)0.0380 (12)
C280.2236 (3)0.0819 (4)0.18263 (17)0.0528 (15)
H280.25930.12820.18700.063*
C290.1935 (3)0.0383 (5)0.14064 (18)0.0631 (18)
H290.20950.05400.11660.076*
C300.1410 (3)0.0274 (5)0.13302 (17)0.0627 (18)
H300.11920.05390.10360.075*
C310.1202 (3)0.0548 (4)0.16902 (15)0.0470 (14)
H310.08440.10140.16410.056*
C320.1507 (2)0.0152 (4)0.21207 (15)0.0376 (12)
C330.1904 (2)0.0967 (4)0.28417 (15)0.0356 (11)
C340.2103 (3)0.1934 (4)0.27291 (17)0.0436 (13)
H340.18730.22310.24430.052*
C350.2626 (3)0.2482 (4)0.30196 (19)0.0604 (17)
H350.27490.31470.29390.072*
C360.2962 (3)0.2022 (5)0.34327 (18)0.0571 (16)
H360.33200.23780.36380.069*
C370.2781 (2)0.1059 (4)0.35466 (15)0.0386 (12)
H370.30310.07490.38250.046*
C380.2235 (2)0.0516 (4)0.32614 (14)0.0301 (10)
C390.2869 (2)0.1660 (4)0.27151 (16)0.0429 (13)
H39A0.32060.12330.26550.064*
H39B0.30150.18670.30340.064*
H39C0.27880.22880.25250.064*
C400.0735 (2)0.0973 (4)0.24384 (15)0.0366 (12)
H40A0.03890.05600.22260.055*
H40B0.06500.10330.27260.055*
H40C0.07450.16740.23140.055*
C410.2244 (2)0.1888 (4)0.46888 (15)0.0305 (11)
C420.1949 (2)0.2835 (4)0.45118 (16)0.0345 (11)
H420.18420.29630.41980.041*
C430.1809 (3)0.3585 (4)0.47771 (19)0.0470 (13)
H430.16020.42170.46460.056*
C440.1968 (3)0.3425 (4)0.5234 (2)0.0585 (16)
H440.18860.39530.54220.070*
C450.2250 (3)0.2480 (4)0.54172 (17)0.0469 (14)
H450.23610.23700.57330.056*
C460.2375 (2)0.1695 (4)0.51516 (15)0.0356 (11)
C470.2139 (2)0.0121 (4)0.52683 (15)0.0350 (11)
C480.1787 (2)0.0102 (4)0.55643 (16)0.0427 (12)
H480.18850.04250.57910.051*
C490.1303 (3)0.0812 (5)0.55451 (17)0.0517 (14)
H490.10750.07890.57570.062*
C500.1159 (3)0.1555 (4)0.52102 (17)0.0467 (13)
H500.08260.20540.51890.056*
C510.1492 (2)0.1588 (4)0.49038 (16)0.0427 (13)
H510.13750.20960.46700.051*
C520.1998 (2)0.0884 (4)0.49323 (14)0.0319 (11)
C530.2967 (2)0.0500 (4)0.47170 (15)0.0334 (11)
C540.3533 (2)0.1058 (4)0.49256 (15)0.0400 (12)
H540.35120.17850.49840.048*
C550.4128 (2)0.0553 (4)0.50488 (17)0.0474 (14)
H550.45150.09360.51920.057*
C560.4163 (2)0.0504 (4)0.49650 (17)0.0459 (13)
H560.45730.08490.50530.055*
C570.3599 (2)0.1058 (4)0.47530 (15)0.0371 (12)
H570.36250.17840.46940.044*
C580.2997 (2)0.0570 (4)0.46250 (14)0.0309 (11)
C590.3147 (2)0.0667 (4)0.57586 (15)0.0479 (14)
H59A0.34900.11590.57520.058*
H59B0.33290.00410.58170.058*
H59C0.29730.08700.59980.058*
C600.2344 (3)0.2094 (4)0.44436 (16)0.0427 (13)
H60A0.19000.23320.42820.064*
H60B0.25360.25390.47090.064*
H60C0.26070.21390.42440.064*
C610.0408 (2)0.0432 (3)0.39382 (13)0.0273 (10)
C620.0637 (2)0.1056 (4)0.43271 (14)0.0309 (11)
H620.10190.08430.45610.037*
C630.0333 (2)0.1961 (3)0.43842 (14)0.0313 (11)
H630.05130.23700.46490.038*
C640.0238 (2)0.2280 (4)0.40555 (15)0.0342 (11)
H640.04520.29090.40880.041*
C650.0486 (2)0.1649 (3)0.36772 (14)0.0291 (10)
H650.08840.18460.34550.035*
C660.0181 (2)0.0751 (3)0.36100 (13)0.0257 (10)
C670.1073 (2)0.0313 (4)0.31871 (14)0.0325 (11)
C680.1663 (2)0.0093 (4)0.28458 (15)0.0372 (12)
H680.16670.03560.26040.045*
C690.2235 (2)0.0522 (4)0.28602 (16)0.0427 (13)
H690.26310.03650.26280.051*
C700.2242 (2)0.1180 (4)0.32079 (16)0.0411 (12)
H700.26410.14550.32210.049*
C710.1657 (2)0.1435 (4)0.35389 (15)0.0348 (11)
H710.16580.19070.37730.042*
C720.1073 (2)0.1012 (4)0.35337 (14)0.0317 (11)
C730.0028 (2)0.1795 (4)0.36796 (14)0.0320 (11)
C740.0188 (2)0.2791 (4)0.34968 (15)0.0356 (11)
H740.05900.30870.34960.043*
C750.0201 (2)0.3376 (4)0.33164 (15)0.0393 (12)
H750.00750.40550.31950.047*
C760.0781 (2)0.2930 (4)0.33209 (14)0.0356 (11)
H760.10590.33060.31970.043*
C770.0964 (2)0.1947 (4)0.35019 (14)0.0325 (11)
H770.13680.16670.35010.039*
C780.0569 (2)0.1339 (3)0.36900 (13)0.0280 (10)
C790.0450 (2)0.0685 (4)0.27994 (14)0.0354 (11)
H79A0.06210.02240.25370.053*
H79B0.00010.08730.28350.053*
H79C0.07150.13210.27540.053*
C800.0478 (2)0.1707 (4)0.42861 (15)0.0432 (13)
H80A0.06580.24170.42350.065*
H80B0.07510.12680.44080.065*
H80C0.00350.17310.45020.065*
Fe10.17367 (3)0.00329 (6)0.40199 (2)0.02762 (18)
Fe20.25881 (3)0.15927 (6)0.38298 (2)0.03122 (19)
N10.31703 (17)0.2743 (3)0.38190 (12)0.0315 (9)
N20.36834 (18)0.4317 (3)0.45443 (13)0.0384 (10)
N30.39530 (19)0.4622 (3)0.37670 (13)0.0399 (10)
N40.20378 (16)0.0392 (3)0.34477 (11)0.0277 (8)
N50.22650 (18)0.1048 (3)0.26126 (12)0.0374 (10)
N60.13593 (18)0.0458 (3)0.25134 (12)0.0330 (9)
N70.24007 (17)0.1133 (3)0.44047 (11)0.0292 (9)
N80.26247 (18)0.0687 (3)0.53236 (12)0.0344 (9)
N90.23263 (18)0.0987 (3)0.45908 (11)0.0317 (9)
N100.08062 (16)0.0371 (3)0.38772 (11)0.0268 (8)
N110.04708 (17)0.0144 (3)0.32030 (11)0.0298 (9)
N120.04644 (17)0.1268 (3)0.38618 (11)0.0282 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.028 (2)0.033 (3)0.035 (3)0.002 (2)0.004 (2)0.002 (2)
C20.034 (3)0.026 (3)0.035 (3)0.001 (2)0.002 (2)0.001 (2)
C30.031 (3)0.034 (3)0.046 (3)0.003 (2)0.007 (2)0.001 (2)
C40.039 (3)0.038 (3)0.061 (4)0.016 (2)0.004 (3)0.006 (3)
C50.040 (3)0.042 (3)0.046 (3)0.004 (2)0.001 (2)0.009 (2)
C60.022 (2)0.040 (3)0.041 (3)0.005 (2)0.000 (2)0.003 (2)
C70.029 (3)0.035 (3)0.041 (3)0.007 (2)0.007 (2)0.005 (2)
C80.036 (3)0.043 (3)0.045 (3)0.007 (3)0.004 (2)0.004 (2)
C90.039 (3)0.045 (3)0.048 (3)0.003 (3)0.014 (2)0.006 (3)
C100.040 (3)0.043 (3)0.063 (4)0.003 (3)0.010 (3)0.003 (3)
C110.034 (3)0.051 (3)0.046 (3)0.004 (3)0.008 (2)0.009 (3)
C120.033 (3)0.038 (3)0.035 (3)0.005 (2)0.007 (2)0.004 (2)
C130.027 (2)0.044 (3)0.032 (3)0.001 (2)0.0016 (19)0.002 (2)
C140.036 (3)0.050 (3)0.036 (3)0.007 (3)0.010 (2)0.002 (2)
C150.032 (3)0.063 (4)0.051 (3)0.007 (3)0.011 (2)0.005 (3)
C160.038 (3)0.055 (4)0.040 (3)0.012 (3)0.012 (2)0.002 (3)
C170.032 (3)0.042 (3)0.032 (3)0.000 (2)0.007 (2)0.001 (2)
C180.031 (3)0.038 (3)0.029 (2)0.001 (2)0.0057 (19)0.003 (2)
C190.038 (3)0.050 (3)0.036 (3)0.002 (3)0.001 (2)0.007 (2)
C200.059 (4)0.058 (4)0.034 (3)0.005 (3)0.003 (2)0.011 (3)
C210.026 (2)0.028 (2)0.025 (2)0.000 (2)0.0004 (18)0.0003 (19)
C220.026 (2)0.035 (3)0.025 (2)0.003 (2)0.0080 (18)0.001 (2)
C230.024 (2)0.027 (3)0.039 (3)0.0000 (19)0.0082 (19)0.003 (2)
C240.024 (2)0.036 (3)0.036 (3)0.003 (2)0.0033 (19)0.008 (2)
C250.026 (2)0.040 (3)0.027 (2)0.004 (2)0.0046 (19)0.003 (2)
C260.024 (2)0.042 (3)0.026 (2)0.007 (2)0.0050 (18)0.005 (2)
C270.038 (3)0.050 (3)0.027 (3)0.002 (2)0.012 (2)0.001 (2)
C280.067 (4)0.062 (4)0.036 (3)0.006 (3)0.025 (3)0.007 (3)
C290.093 (5)0.073 (4)0.030 (3)0.016 (4)0.030 (3)0.007 (3)
C300.095 (5)0.070 (4)0.020 (3)0.008 (4)0.015 (3)0.008 (3)
C310.067 (4)0.041 (3)0.028 (3)0.002 (3)0.008 (2)0.006 (2)
C320.041 (3)0.043 (3)0.024 (2)0.010 (2)0.005 (2)0.002 (2)
C330.036 (3)0.035 (3)0.034 (3)0.003 (2)0.009 (2)0.005 (2)
C340.047 (3)0.040 (3)0.039 (3)0.011 (3)0.007 (2)0.005 (2)
C350.067 (4)0.048 (4)0.057 (4)0.029 (3)0.008 (3)0.014 (3)
C360.054 (4)0.064 (4)0.046 (3)0.026 (3)0.007 (3)0.001 (3)
C370.035 (3)0.048 (3)0.030 (3)0.012 (2)0.007 (2)0.000 (2)
C380.025 (2)0.040 (3)0.027 (2)0.006 (2)0.0103 (18)0.002 (2)
C390.028 (3)0.064 (4)0.037 (3)0.002 (3)0.012 (2)0.002 (3)
C400.039 (3)0.035 (3)0.031 (3)0.002 (2)0.004 (2)0.000 (2)
C410.022 (2)0.037 (3)0.033 (3)0.002 (2)0.0090 (18)0.008 (2)
C420.035 (3)0.035 (3)0.036 (3)0.000 (2)0.016 (2)0.003 (2)
C430.050 (3)0.037 (3)0.059 (4)0.000 (3)0.024 (3)0.011 (3)
C440.073 (4)0.042 (4)0.072 (4)0.008 (3)0.039 (3)0.023 (3)
C450.064 (4)0.047 (3)0.036 (3)0.007 (3)0.025 (3)0.014 (3)
C460.038 (3)0.035 (3)0.035 (3)0.010 (2)0.013 (2)0.013 (2)
C470.039 (3)0.035 (3)0.027 (2)0.001 (2)0.006 (2)0.005 (2)
C480.047 (3)0.050 (3)0.035 (3)0.008 (3)0.019 (2)0.003 (2)
C490.058 (4)0.067 (4)0.037 (3)0.008 (3)0.025 (3)0.001 (3)
C500.044 (3)0.055 (4)0.042 (3)0.007 (3)0.015 (2)0.011 (3)
C510.041 (3)0.045 (3)0.034 (3)0.003 (3)0.001 (2)0.001 (2)
C520.034 (3)0.036 (3)0.023 (2)0.001 (2)0.0043 (19)0.003 (2)
C530.029 (2)0.043 (3)0.029 (2)0.007 (2)0.0106 (19)0.000 (2)
C540.043 (3)0.044 (3)0.033 (3)0.009 (2)0.013 (2)0.010 (2)
C550.024 (3)0.058 (4)0.054 (3)0.012 (3)0.004 (2)0.012 (3)
C560.032 (3)0.054 (4)0.050 (3)0.001 (3)0.010 (2)0.006 (3)
C570.029 (3)0.049 (3)0.031 (3)0.006 (2)0.006 (2)0.006 (2)
C580.028 (2)0.037 (3)0.029 (2)0.005 (2)0.0102 (19)0.003 (2)
C590.045 (3)0.067 (4)0.027 (3)0.012 (3)0.006 (2)0.007 (3)
C600.053 (3)0.033 (3)0.035 (3)0.003 (2)0.004 (2)0.002 (2)
C610.027 (2)0.034 (3)0.021 (2)0.002 (2)0.0083 (18)0.0014 (19)
C620.029 (2)0.036 (3)0.027 (2)0.000 (2)0.0081 (19)0.002 (2)
C630.040 (3)0.030 (3)0.026 (2)0.008 (2)0.013 (2)0.007 (2)
C640.033 (3)0.033 (3)0.035 (3)0.005 (2)0.009 (2)0.000 (2)
C650.033 (2)0.030 (3)0.024 (2)0.002 (2)0.0077 (18)0.005 (2)
C660.026 (2)0.028 (3)0.022 (2)0.0020 (19)0.0065 (17)0.0036 (19)
C670.030 (2)0.042 (3)0.024 (2)0.003 (2)0.0069 (18)0.004 (2)
C680.033 (3)0.046 (3)0.028 (2)0.009 (2)0.0038 (19)0.000 (2)
C690.027 (3)0.066 (4)0.030 (3)0.008 (3)0.003 (2)0.004 (3)
C700.027 (2)0.055 (3)0.040 (3)0.001 (2)0.008 (2)0.010 (3)
C710.031 (3)0.045 (3)0.029 (2)0.001 (2)0.011 (2)0.000 (2)
C720.028 (2)0.038 (3)0.024 (2)0.000 (2)0.0025 (18)0.005 (2)
C730.033 (3)0.035 (3)0.024 (2)0.007 (2)0.0031 (19)0.002 (2)
C740.030 (3)0.034 (3)0.037 (3)0.003 (2)0.003 (2)0.003 (2)
C750.040 (3)0.040 (3)0.032 (3)0.006 (2)0.004 (2)0.007 (2)
C760.035 (3)0.041 (3)0.027 (2)0.013 (2)0.0050 (19)0.002 (2)
C770.030 (2)0.040 (3)0.024 (2)0.005 (2)0.0035 (18)0.001 (2)
C780.029 (2)0.033 (3)0.020 (2)0.006 (2)0.0051 (18)0.0056 (19)
C790.037 (3)0.042 (3)0.024 (2)0.001 (2)0.007 (2)0.003 (2)
C800.038 (3)0.056 (3)0.032 (3)0.004 (3)0.007 (2)0.009 (2)
Fe10.0246 (3)0.0327 (4)0.0226 (3)0.0008 (3)0.0037 (3)0.0012 (3)
Fe20.0281 (4)0.0352 (4)0.0279 (4)0.0007 (3)0.0058 (3)0.0004 (3)
N10.0237 (19)0.030 (2)0.037 (2)0.0012 (17)0.0041 (16)0.0004 (17)
N20.026 (2)0.043 (3)0.035 (2)0.0028 (19)0.0040 (17)0.0025 (19)
N30.037 (2)0.038 (2)0.034 (2)0.0011 (19)0.0020 (18)0.0014 (19)
N40.0224 (18)0.036 (2)0.0243 (19)0.0062 (16)0.0071 (15)0.0028 (16)
N50.031 (2)0.050 (3)0.030 (2)0.0004 (19)0.0092 (17)0.0023 (19)
N60.032 (2)0.037 (2)0.025 (2)0.0025 (18)0.0015 (16)0.0009 (17)
N70.0236 (19)0.036 (2)0.026 (2)0.0035 (17)0.0058 (15)0.0040 (17)
N80.032 (2)0.042 (2)0.025 (2)0.0081 (19)0.0049 (16)0.0054 (18)
N90.036 (2)0.031 (2)0.0237 (19)0.0001 (18)0.0042 (16)0.0003 (17)
N100.0184 (17)0.029 (2)0.028 (2)0.0028 (16)0.0013 (14)0.0057 (16)
N110.031 (2)0.033 (2)0.0239 (19)0.0048 (17)0.0070 (15)0.0022 (16)
N120.0223 (18)0.034 (2)0.0244 (19)0.0018 (16)0.0031 (15)0.0019 (16)
Geometric parameters (Å, º) top
C1—C61.401 (6)C42—H420.9500
C1—C21.406 (6)C43—C441.375 (8)
C1—N11.426 (6)C43—H430.9500
C2—C31.376 (6)C44—C451.390 (7)
C2—H20.9500C44—H440.9500
C3—C41.375 (7)C45—C461.386 (6)
C3—H30.9500C45—H450.9500
C4—C51.401 (6)C46—N81.432 (6)
C4—H40.9500C47—C481.384 (6)
C5—C61.370 (7)C47—C521.394 (6)
C5—H50.9500C47—N81.446 (6)
C6—N21.456 (5)C48—C491.378 (7)
C7—C81.388 (7)C48—H480.9500
C7—C121.416 (7)C49—C501.373 (7)
C7—N21.434 (6)C49—H490.9500
C8—C91.391 (7)C50—C511.381 (7)
C8—H80.9500C50—H500.9500
C9—C101.378 (8)C51—C521.401 (7)
C9—H90.9500C51—H510.9500
C10—C111.403 (7)C52—N91.476 (6)
C10—H100.9500C53—C541.386 (6)
C11—C121.410 (7)C53—C581.401 (6)
C11—H110.9500C53—N91.458 (6)
C12—N31.395 (6)C54—C551.382 (7)
C13—C141.377 (7)C54—H540.9500
C13—C181.411 (7)C55—C561.382 (7)
C13—N31.456 (6)C55—H550.9500
C14—C151.381 (7)C56—C571.383 (6)
C14—H140.9500C56—H560.9500
C15—C161.397 (7)C57—C581.385 (6)
C15—H150.9500C57—H570.9500
C16—C171.372 (7)C58—N71.446 (5)
C16—H160.9500C59—N81.461 (5)
C17—C181.403 (6)C59—H59A0.9800
C17—H170.9500C59—H59B0.9800
C18—N11.386 (6)C59—H59C0.9800
C19—N21.468 (6)C60—N91.492 (6)
C19—H19A0.9800C60—H60A0.9800
C19—H19B0.9800C60—H60B0.9800
C19—H19C0.9800C60—H60C0.9800
C20—N31.459 (6)C61—N101.395 (5)
C20—H20A0.9800C61—C621.405 (6)
C20—H20B0.9800C61—C661.414 (6)
C20—H20C0.9800C62—C631.372 (6)
C21—C221.404 (6)C62—H620.9500
C21—C261.417 (6)C63—C641.389 (6)
C21—N41.436 (5)C63—H630.9500
C21—Fe22.426 (4)C64—C651.389 (6)
C22—C231.388 (6)C64—H640.9500
C22—H220.9500C65—C661.375 (6)
C23—C241.384 (6)C65—H650.9500
C23—H230.9500C66—N111.449 (5)
C24—C251.386 (6)C67—C681.403 (6)
C24—H240.9500C67—C721.407 (6)
C25—C261.376 (6)C67—N111.421 (6)
C25—H250.9500C68—C691.375 (7)
C26—N51.445 (6)C68—H680.9500
C27—C281.394 (7)C69—C701.381 (7)
C27—N51.398 (6)C69—H690.9500
C27—C321.419 (7)C70—C711.391 (6)
C28—C291.381 (7)C70—H700.9500
C28—H280.9500C71—C721.387 (6)
C29—C301.373 (8)C71—H710.9500
C29—H290.9500C72—N121.422 (5)
C30—C311.393 (7)C73—C741.392 (6)
C30—H300.9500C73—C781.414 (6)
C31—C321.390 (6)C73—N121.428 (6)
C31—H310.9500C74—C751.383 (7)
C32—N61.427 (6)C74—H740.9500
C33—C341.392 (6)C75—C761.381 (7)
C33—C381.401 (6)C75—H750.9500
C33—N61.444 (6)C76—C771.382 (6)
C34—C351.390 (7)C76—H760.9500
C34—H340.9500C77—C781.423 (6)
C35—C361.392 (7)C77—H770.9500
C35—H350.9500C78—N101.393 (5)
C36—C371.373 (7)C79—N111.456 (5)
C36—H360.9500C79—H79A0.9800
C37—C381.413 (6)C79—H79B0.9800
C37—H370.9500C79—H79C0.9800
C38—N41.426 (6)C80—N121.454 (6)
C39—N51.470 (6)C80—H80A0.9800
C39—H39A0.9800C80—H80B0.9800
C39—H39B0.9800C80—H80C0.9800
C39—H39C0.9800Fe1—N101.992 (3)
C40—N61.458 (6)Fe1—N72.091 (4)
C40—H40A0.9800Fe1—N42.154 (4)
C40—H40B0.9800Fe1—N92.245 (3)
C40—H40C0.9800Fe1—Fe22.9121 (10)
C41—C421.396 (6)Fe2—N11.947 (4)
C41—C461.407 (6)Fe2—N72.061 (4)
C41—N71.429 (5)Fe2—N42.068 (4)
C42—C431.367 (6)
C6—C1—C2117.3 (4)C50—C51—H51119.4
C6—C1—N1124.8 (4)C52—C51—H51119.4
C2—C1—N1117.5 (4)C47—C52—C51118.0 (5)
C3—C2—C1121.2 (4)C47—C52—N9124.9 (4)
C3—C2—H2119.4C51—C52—N9117.0 (4)
C1—C2—H2119.4C54—C53—C58120.2 (5)
C4—C3—C2121.1 (4)C54—C53—N9122.0 (4)
C4—C3—H3119.4C58—C53—N9117.7 (4)
C2—C3—H3119.4C55—C54—C53119.8 (5)
C3—C4—C5118.1 (5)C55—C54—H54120.1
C3—C4—H4120.9C53—C54—H54120.1
C5—C4—H4120.9C56—C55—C54120.5 (5)
C6—C5—C4121.4 (5)C56—C55—H55119.8
C6—C5—H5119.3C54—C55—H55119.8
C4—C5—H5119.3C55—C56—C57119.7 (5)
C5—C6—C1120.8 (4)C55—C56—H56120.2
C5—C6—N2118.6 (4)C57—C56—H56120.2
C1—C6—N2120.7 (4)C56—C57—C58120.9 (5)
C8—C7—C12120.0 (5)C56—C57—H57119.5
C8—C7—N2124.0 (5)C58—C57—H57119.5
C12—C7—N2115.9 (4)C57—C58—C53118.9 (4)
C7—C8—C9121.2 (5)C57—C58—N7122.0 (4)
C7—C8—H8119.4C53—C58—N7119.2 (4)
C9—C8—H8119.4N8—C59—H59A109.5
C10—C9—C8119.4 (5)N8—C59—H59B109.5
C10—C9—H9120.3H59A—C59—H59B109.5
C8—C9—H9120.3N8—C59—H59C109.5
C9—C10—C11120.5 (5)H59A—C59—H59C109.5
C9—C10—H10119.8H59B—C59—H59C109.5
C11—C10—H10119.8N9—C60—H60A109.5
C10—C11—C12120.5 (5)N9—C60—H60B109.5
C10—C11—H11119.7H60A—C60—H60B109.5
C12—C11—H11119.7N9—C60—H60C109.5
N3—C12—C11123.3 (5)H60A—C60—H60C109.5
N3—C12—C7118.7 (4)H60B—C60—H60C109.5
C11—C12—C7118.0 (5)N10—C61—C62118.5 (4)
C14—C13—C18120.8 (5)N10—C61—C66124.5 (4)
C14—C13—N3118.4 (4)C62—C61—C66116.5 (4)
C18—C13—N3120.7 (4)C63—C62—C61122.9 (4)
C13—C14—C15121.9 (5)C63—C62—H62118.5
C13—C14—H14119.1C61—C62—H62118.5
C15—C14—H14119.1C62—C63—C64120.1 (4)
C14—C15—C16118.2 (5)C62—C63—H63120.0
C14—C15—H15120.9C64—C63—H63120.0
C16—C15—H15120.9C65—C64—C63117.8 (4)
C17—C16—C15120.1 (5)C65—C64—H64121.1
C17—C16—H16119.9C63—C64—H64121.1
C15—C16—H16119.9C66—C65—C64122.9 (4)
C16—C17—C18122.6 (5)C66—C65—H65118.6
C16—C17—H17118.7C64—C65—H65118.6
C18—C17—H17118.7C65—C66—C61119.8 (4)
N1—C18—C17117.5 (4)C65—C66—N11119.2 (4)
N1—C18—C13126.2 (4)C61—C66—N11121.0 (4)
C17—C18—C13116.2 (4)C68—C67—C72119.0 (4)
N2—C19—H19A109.5C68—C67—N11123.1 (4)
N2—C19—H19B109.5C72—C67—N11117.9 (4)
H19A—C19—H19B109.5C69—C68—C67120.4 (5)
N2—C19—H19C109.5C69—C68—H68119.8
H19A—C19—H19C109.5C67—C68—H68119.8
H19B—C19—H19C109.5C68—C69—C70120.9 (4)
N3—C20—H20A109.5C68—C69—H69119.5
N3—C20—H20B109.5C70—C69—H69119.5
H20A—C20—H20B109.5C69—C70—C71119.2 (5)
N3—C20—H20C109.5C69—C70—H70120.4
H20A—C20—H20C109.5C71—C70—H70120.4
H20B—C20—H20C109.5C72—C71—C70121.2 (5)
C22—C21—C26117.8 (4)C72—C71—H71119.4
C22—C21—N4117.8 (4)C70—C71—H71119.4
C26—C21—N4124.3 (4)C71—C72—C67119.2 (4)
C22—C21—Fe295.9 (3)C71—C72—N12122.8 (4)
C26—C21—Fe2112.8 (3)C67—C72—N12118.0 (4)
N4—C21—Fe258.2 (2)C74—C73—C78119.3 (4)
C23—C22—C21120.9 (4)C74—C73—N12119.1 (4)
C23—C22—H22119.5C78—C73—N12121.6 (4)
C21—C22—H22119.5C75—C74—C73123.9 (5)
C24—C23—C22120.6 (4)C75—C74—H74118.0
C24—C23—H23119.7C73—C74—H74118.0
C22—C23—H23119.7C76—C75—C74117.0 (5)
C23—C24—C25118.9 (4)C76—C75—H75121.5
C23—C24—H24120.6C74—C75—H75121.5
C25—C24—H24120.6C75—C76—C77121.2 (5)
C26—C25—C24121.8 (4)C75—C76—H76119.4
C26—C25—H25119.1C77—C76—H76119.4
C24—C25—H25119.1C76—C77—C78122.3 (4)
C25—C26—C21119.9 (4)C76—C77—H77118.9
C25—C26—N5120.3 (4)C78—C77—H77118.9
C21—C26—N5119.7 (4)N10—C78—C73125.8 (4)
C28—C27—N5124.0 (5)N10—C78—C77117.9 (4)
C28—C27—C32118.9 (4)C73—C78—C77116.3 (4)
N5—C27—C32117.1 (4)N11—C79—H79A109.5
C29—C28—C27120.5 (6)N11—C79—H79B109.5
C29—C28—H28119.8H79A—C79—H79B109.5
C27—C28—H28119.8N11—C79—H79C109.5
C30—C29—C28121.2 (5)H79A—C79—H79C109.5
C30—C29—H29119.4H79B—C79—H79C109.5
C28—C29—H29119.4N12—C80—H80A109.5
C29—C30—C31119.1 (5)N12—C80—H80B109.5
C29—C30—H30120.5H80A—C80—H80B109.5
C31—C30—H30120.5N12—C80—H80C109.5
C32—C31—C30121.2 (5)H80A—C80—H80C109.5
C32—C31—H31119.4H80B—C80—H80C109.5
C30—C31—H31119.4N10—Fe1—N7139.63 (14)
C31—C32—C27119.0 (5)N10—Fe1—N4115.65 (13)
C31—C32—N6124.6 (5)N7—Fe1—N489.81 (14)
C27—C32—N6116.4 (4)N10—Fe1—N9107.53 (14)
C34—C33—C38119.8 (4)N7—Fe1—N979.85 (13)
C34—C33—N6118.0 (4)N4—Fe1—N9122.57 (14)
C38—C33—N6122.3 (4)N10—Fe1—Fe2143.01 (11)
C35—C34—C33122.4 (5)N7—Fe1—Fe245.05 (10)
C35—C34—H34118.8N4—Fe1—Fe245.18 (10)
C33—C34—H34118.8N9—Fe1—Fe2108.97 (10)
C34—C35—C36117.7 (5)N1—Fe2—N7123.16 (15)
C34—C35—H35121.1N1—Fe2—N4143.61 (15)
C36—C35—H35121.1N7—Fe2—N493.04 (14)
C37—C36—C35120.9 (5)N1—Fe2—C21119.49 (15)
C37—C36—H36119.6N7—Fe2—C21110.96 (15)
C35—C36—H36119.6N4—Fe2—C2136.19 (14)
C36—C37—C38121.8 (5)N1—Fe2—Fe1168.73 (11)
C36—C37—H37119.1N7—Fe2—Fe145.87 (10)
C38—C37—H37119.1N4—Fe2—Fe147.62 (10)
C33—C38—C37117.4 (4)C21—Fe2—Fe168.99 (11)
C33—C38—N4126.0 (4)C18—N1—C1122.3 (4)
C37—C38—N4116.3 (4)C18—N1—Fe2128.7 (3)
N5—C39—H39A109.5C1—N1—Fe2108.3 (3)
N5—C39—H39B109.5C7—N2—C6109.9 (4)
H39A—C39—H39B109.5C7—N2—C19115.6 (4)
N5—C39—H39C109.5C6—N2—C19112.0 (4)
H39A—C39—H39C109.5C12—N3—C13116.3 (4)
H39B—C39—H39C109.5C12—N3—C20118.6 (4)
N6—C40—H40A109.5C13—N3—C20112.2 (4)
N6—C40—H40B109.5C38—N4—C21120.8 (3)
H40A—C40—H40B109.5C38—N4—Fe2130.2 (3)
N6—C40—H40C109.5C21—N4—Fe285.6 (2)
H40A—C40—H40C109.5C38—N4—Fe1112.6 (3)
H40B—C40—H40C109.5C21—N4—Fe1114.8 (3)
C42—C41—C46118.2 (4)Fe2—N4—Fe187.20 (13)
C42—C41—N7120.6 (4)C27—N5—C26113.2 (4)
C46—C41—N7121.1 (4)C27—N5—C39117.9 (4)
C43—C42—C41122.0 (5)C26—N5—C39113.7 (4)
C43—C42—H42119.0C32—N6—C33112.0 (4)
C41—C42—H42119.0C32—N6—C40116.6 (4)
C42—C43—C44120.0 (5)C33—N6—C40114.5 (4)
C42—C43—H43120.0C41—N7—C58113.5 (3)
C44—C43—H43120.0C41—N7—Fe2120.7 (3)
C43—C44—C45119.1 (5)C58—N7—Fe298.9 (3)
C43—C44—H44120.4C41—N7—Fe1123.5 (3)
C45—C44—H44120.4C58—N7—Fe1106.5 (3)
C46—C45—C44121.7 (5)Fe2—N7—Fe189.07 (13)
C46—C45—H45119.1C46—N8—C47115.1 (4)
C44—C45—H45119.1C46—N8—C59116.8 (4)
C45—C46—C41118.7 (5)C47—N8—C59114.4 (4)
C45—C46—N8123.3 (4)C53—N9—C52114.4 (3)
C41—C46—N8118.0 (4)C53—N9—C60111.7 (4)
C48—C47—C52119.2 (5)C52—N9—C60112.1 (4)
C48—C47—N8116.8 (4)C53—N9—Fe1102.3 (3)
C52—C47—N8124.1 (4)C52—N9—Fe1104.0 (3)
C49—C48—C47122.9 (5)C60—N9—Fe1111.6 (3)
C49—C48—H48118.6C78—N10—C61123.3 (3)
C47—C48—H48118.6C78—N10—Fe1122.2 (3)
C50—C49—C48117.8 (5)C61—N10—Fe1114.2 (3)
C50—C49—H49121.1C67—N11—C66112.4 (3)
C48—C49—H49121.1C67—N11—C79117.2 (3)
C49—C50—C51121.0 (5)C66—N11—C79112.6 (3)
C49—C50—H50119.5C72—N12—C73113.7 (3)
C51—C50—H50119.5C72—N12—C80117.2 (4)
C50—C51—C52121.1 (5)C73—N12—C80113.6 (4)
C6—C1—C2—C32.4 (7)N11—C67—C72—N123.9 (6)
N1—C1—C2—C3171.3 (4)C78—C73—C74—C750.7 (7)
C1—C2—C3—C40.4 (8)N12—C73—C74—C75179.2 (4)
C2—C3—C4—C52.1 (9)C73—C74—C75—C760.1 (7)
C3—C4—C5—C62.6 (9)C74—C75—C76—C770.6 (7)
C4—C5—C6—C10.6 (8)C75—C76—C77—C780.4 (7)
C4—C5—C6—N2180.0 (5)C74—C73—C78—N10177.4 (4)
C2—C1—C6—C51.9 (7)N12—C73—C78—N101.2 (6)
N1—C1—C6—C5171.3 (5)C74—C73—C78—C770.8 (6)
C2—C1—C6—N2177.6 (4)N12—C73—C78—C77179.4 (4)
N1—C1—C6—N29.2 (8)C76—C77—C78—N10178.0 (4)
C12—C7—C8—C94.0 (7)C76—C77—C78—C730.4 (6)
N2—C7—C8—C9174.4 (4)C17—C18—N1—C1173.8 (4)
C7—C8—C9—C102.1 (8)C13—C18—N1—C110.1 (7)
C8—C9—C10—C115.5 (8)C17—C18—N1—Fe24.8 (6)
C9—C10—C11—C122.8 (8)C13—C18—N1—Fe2179.1 (3)
C10—C11—C12—N3179.3 (5)C6—C1—N1—C1854.7 (7)
C10—C11—C12—C73.2 (7)C2—C1—N1—C18132.1 (5)
C8—C7—C12—N3175.8 (4)C6—C1—N1—Fe2116.3 (5)
N2—C7—C12—N35.6 (6)C2—C1—N1—Fe256.9 (5)
C8—C7—C12—C116.6 (7)C8—C7—N2—C6121.6 (5)
N2—C7—C12—C11171.9 (4)C12—C7—N2—C656.9 (5)
C18—C13—C14—C153.2 (7)C8—C7—N2—C196.4 (6)
N3—C13—C14—C15173.0 (4)C12—C7—N2—C19175.1 (4)
C13—C14—C15—C160.4 (7)C5—C6—N2—C763.7 (6)
C14—C15—C16—C171.8 (7)C1—C6—N2—C7115.8 (5)
C15—C16—C17—C180.4 (7)C5—C6—N2—C1966.3 (6)
C16—C17—C18—N1179.6 (4)C1—C6—N2—C19114.2 (5)
C16—C17—C18—C133.9 (7)C11—C12—N3—C13118.5 (5)
C14—C13—C18—N1178.6 (4)C7—C12—N3—C1364.1 (6)
N3—C13—C18—N15.3 (7)C11—C12—N3—C2020.1 (7)
C14—C13—C18—C175.2 (7)C7—C12—N3—C20157.4 (4)
N3—C13—C18—C17170.9 (4)C14—C13—N3—C1265.1 (6)
C26—C21—C22—C232.2 (6)C18—C13—N3—C12118.7 (5)
N4—C21—C22—C23179.0 (4)C14—C13—N3—C2076.0 (5)
Fe2—C21—C22—C23121.9 (4)C18—C13—N3—C20100.2 (5)
C21—C22—C23—C240.5 (6)C33—C38—N4—C2130.0 (7)
C22—C23—C24—C252.7 (6)C37—C38—N4—C21156.3 (4)
C23—C24—C25—C262.2 (7)C33—C38—N4—Fe2142.7 (4)
C24—C25—C26—C210.5 (7)C37—C38—N4—Fe243.7 (6)
C24—C25—C26—N5179.3 (4)C33—C38—N4—Fe1110.9 (5)
C22—C21—C26—C252.7 (6)C37—C38—N4—Fe162.7 (5)
N4—C21—C26—C25179.3 (4)C22—C21—N4—C38145.9 (4)
Fe2—C21—C26—C25113.1 (4)C26—C21—N4—C3837.5 (6)
C22—C21—C26—N5177.1 (4)Fe2—C21—N4—C38135.0 (4)
N4—C21—C26—N50.5 (6)C22—C21—N4—Fe279.1 (4)
Fe2—C21—C26—N566.7 (5)C26—C21—N4—Fe297.5 (4)
N5—C27—C28—C29175.5 (5)C22—C21—N4—Fe15.8 (5)
C32—C27—C28—C293.5 (8)C26—C21—N4—Fe1177.7 (3)
C27—C28—C29—C301.1 (10)Fe2—C21—N4—Fe184.8 (2)
C28—C29—C30—C313.6 (10)C28—C27—N5—C26124.2 (5)
C29—C30—C31—C321.3 (9)C32—C27—N5—C2654.8 (6)
C30—C31—C32—C273.3 (8)C28—C27—N5—C3912.1 (7)
C30—C31—C32—N6174.6 (5)C32—C27—N5—C39168.9 (4)
C28—C27—C32—C315.7 (7)C25—C26—N5—C2759.5 (6)
N5—C27—C32—C31173.4 (4)C21—C26—N5—C27120.7 (4)
C28—C27—C32—N6172.5 (4)C25—C26—N5—C3978.7 (5)
N5—C27—C32—N68.5 (6)C21—C26—N5—C39101.1 (5)
C38—C33—C34—C350.1 (8)C31—C32—N6—C33116.0 (5)
N6—C33—C34—C35179.3 (5)C27—C32—N6—C3362.0 (5)
C33—C34—C35—C361.2 (9)C31—C32—N6—C4018.5 (7)
C34—C35—C36—C370.2 (10)C27—C32—N6—C40163.5 (4)
C35—C36—C37—C382.7 (9)C34—C33—N6—C3266.3 (6)
C34—C33—C38—C372.5 (7)C38—C33—N6—C32113.1 (5)
N6—C33—C38—C37176.8 (4)C34—C33—N6—C4069.3 (6)
C34—C33—C38—N4171.1 (5)C38—C33—N6—C40111.4 (5)
N6—C33—C38—N49.6 (7)C42—C41—N7—C58144.3 (4)
C36—C37—C38—C333.9 (8)C46—C41—N7—C5836.4 (6)
C36—C37—C38—N4170.3 (5)C42—C41—N7—Fe227.3 (5)
C46—C41—C42—C432.5 (7)C46—C41—N7—Fe2153.4 (3)
N7—C41—C42—C43178.2 (4)C42—C41—N7—Fe184.5 (5)
C41—C42—C43—C441.0 (8)C46—C41—N7—Fe194.8 (4)
C42—C43—C44—C452.2 (8)C57—C58—N7—C4167.4 (6)
C43—C44—C45—C460.1 (9)C53—C58—N7—C41111.8 (5)
C44—C45—C46—C413.6 (8)C57—C58—N7—Fe261.8 (4)
C44—C45—C46—N8175.8 (5)C53—C58—N7—Fe2119.0 (4)
C42—C41—C46—C454.7 (7)C57—C58—N7—Fe1153.5 (4)
N7—C41—C46—C45176.0 (4)C53—C58—N7—Fe127.3 (5)
C42—C41—C46—N8174.7 (4)C45—C46—N8—C4795.8 (5)
N7—C41—C46—N84.6 (6)C41—C46—N8—C4783.6 (5)
C52—C47—C48—C490.5 (8)C45—C46—N8—C5942.5 (7)
N8—C47—C48—C49178.8 (5)C41—C46—N8—C59138.1 (4)
C47—C48—C49—C501.3 (8)C48—C47—N8—C4677.2 (5)
C48—C49—C50—C510.1 (8)C52—C47—N8—C46101.1 (5)
C49—C50—C51—C521.8 (8)C48—C47—N8—C5962.1 (6)
C48—C47—C52—C511.4 (7)C52—C47—N8—C59119.6 (5)
N8—C47—C52—C51176.8 (4)C54—C53—N9—C5293.7 (5)
C48—C47—C52—N9179.1 (4)C58—C53—N9—C5285.6 (5)
N8—C47—C52—N90.8 (7)C54—C53—N9—C6034.9 (6)
C50—C51—C52—C472.6 (7)C58—C53—N9—C60145.8 (4)
C50—C51—C52—N9179.6 (4)C54—C53—N9—Fe1154.5 (4)
C58—C53—C54—C550.9 (7)C58—C53—N9—Fe126.2 (4)
N9—C53—C54—C55178.4 (4)C47—C52—N9—C5321.8 (6)
C53—C54—C55—C560.1 (8)C51—C52—N9—C53160.5 (4)
C54—C55—C56—C570.6 (8)C47—C52—N9—C60150.3 (4)
C55—C56—C57—C580.3 (8)C51—C52—N9—C6032.1 (5)
C56—C57—C58—C530.5 (7)C47—C52—N9—Fe189.0 (4)
C56—C57—C58—N7179.7 (4)C51—C52—N9—Fe188.7 (4)
C54—C53—C58—C571.1 (7)C73—C78—N10—C6123.2 (6)
N9—C53—C58—C57178.2 (4)C77—C78—N10—C61158.6 (4)
C54—C53—C58—N7179.6 (4)C73—C78—N10—Fe1163.5 (3)
N9—C53—C58—N71.0 (6)C77—C78—N10—Fe114.7 (5)
N10—C61—C62—C63169.3 (4)C62—C61—N10—C78142.7 (4)
C66—C61—C62—C633.2 (7)C66—C61—N10—C7845.4 (6)
C61—C62—C63—C642.0 (7)C62—C61—N10—Fe143.5 (5)
C62—C63—C64—C650.8 (7)C66—C61—N10—Fe1128.4 (4)
C63—C64—C65—C662.2 (7)C68—C67—N11—C66119.5 (5)
C64—C65—C66—C610.9 (7)C72—C67—N11—C6659.9 (5)
C64—C65—C66—N11179.4 (4)C68—C67—N11—C7913.2 (6)
N10—C61—C66—C65170.3 (4)C72—C67—N11—C79167.4 (4)
C62—C61—C66—C651.7 (6)C65—C66—N11—C6766.3 (5)
N10—C61—C66—N1110.0 (7)C61—C66—N11—C67113.4 (5)
C62—C61—C66—N11178.0 (4)C65—C66—N11—C7968.6 (5)
C72—C67—C68—C692.5 (7)C61—C66—N11—C79111.7 (4)
N11—C67—C68—C69176.9 (4)C71—C72—N12—C73116.0 (5)
C67—C68—C69—C700.2 (8)C67—C72—N12—C7363.0 (5)
C68—C69—C70—C712.1 (8)C71—C72—N12—C8019.9 (6)
C69—C70—C71—C722.2 (7)C67—C72—N12—C80161.1 (4)
C70—C71—C72—C670.0 (7)C74—C73—N12—C7265.5 (5)
C70—C71—C72—N12178.9 (4)C78—C73—N12—C72116.0 (4)
C68—C67—C72—C712.4 (7)C74—C73—N12—C8072.0 (5)
N11—C67—C72—C71177.1 (4)C78—C73—N12—C80106.6 (5)
C68—C67—C72—N12176.6 (4)
Bis(µ-1,4-dimethyltribenzo[b,e,h][1,4,7]triazacyclonona-2,5,8-trien-7-ido-κN7)bis(tetrahydrofuran-κO)iron(II) (10) top
Crystal data top
[Fe(C20H18N3)2(C4H8O)2]Dx = 1.288 Mg m3
Mr = 800.80Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, PbcaCell parameters from 9933 reflections
a = 15.9624 (12) Åθ = 3.9–66.7°
b = 15.8047 (11) ŵ = 3.29 mm1
c = 32.747 (2) ÅT = 100 K
V = 8261.5 (10) Å3Block, green
Z = 80.11 × 0.10 × 0.06 mm
F(000) = 3392
Data collection top
Bruker X8 Prospector CCD
diffractometer
7194 independent reflections
Radiation source: I-mu-S microsource X-ray tube5411 reflections with I > 2σ(I)
Laterally graded multilayer (Goebel) mirror monochromatorRint = 0.055
ω and phi scansθmax = 66.7°, θmin = 3.9°
Absorption correction: multi-scan
(APEX2; Bruker, 2014)
h = 1018
Tmin = 0.569, Tmax = 0.753k = 1818
23792 measured reflectionsl = 3138
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0545P)2 + 1.2424P]
where P = (Fo2 + 2Fc2)/3
7194 reflections(Δ/σ)max = 0.002
555 parametersΔρmax = 0.45 e Å3
132 restraintsΔρmin = 0.28 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. One THF ligand is disordered with two alternative orientations. The two moieties were restrained to have similar geometries, and the Uij components of their atoms' ADPs were restrained to be similar if closer than 1.7 Angstrom. Subject to these conditions the occupancy ratio refined to 0.790 (8) to 0.210 (8). Reflection 0 0 2 was affected by the beam stop and was omitted from the refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.01642 (16)0.58940 (13)0.32908 (7)0.0168 (5)
C20.09943 (16)0.58486 (14)0.31399 (7)0.0200 (5)
H20.14170.56150.33100.024*
C30.12151 (18)0.61286 (14)0.27560 (7)0.0226 (5)
H30.17760.60630.26640.027*
C40.06276 (18)0.65050 (15)0.25038 (7)0.0234 (6)
H40.07750.66990.22390.028*
C50.01885 (17)0.65892 (14)0.26520 (7)0.0208 (5)
H50.05960.68610.24860.025*
C60.04262 (16)0.62894 (13)0.30332 (7)0.0175 (5)
C70.15464 (17)0.72340 (15)0.31940 (7)0.0210 (5)
C80.21592 (18)0.76162 (16)0.29572 (8)0.0272 (6)
H80.24520.72930.27590.033*
C90.2349 (2)0.84726 (17)0.30086 (9)0.0355 (7)
H90.27760.87300.28490.043*
C100.1909 (2)0.89430 (17)0.32932 (9)0.0378 (7)
H100.20190.95310.33210.045*
C110.13083 (19)0.85648 (16)0.35387 (8)0.0305 (6)
H110.10120.88950.37330.037*
C120.11369 (17)0.77097 (15)0.35020 (7)0.0216 (5)
C130.09703 (16)0.65585 (15)0.39656 (7)0.0191 (5)
C140.16313 (17)0.67221 (16)0.42292 (7)0.0242 (6)
H140.18380.72840.42520.029*
C150.19976 (17)0.60877 (17)0.44604 (8)0.0286 (6)
H150.24450.62120.46420.034*
C160.17007 (18)0.52737 (17)0.44225 (8)0.0288 (6)
H160.19400.48330.45820.035*
C170.10565 (17)0.50939 (15)0.41537 (8)0.0247 (6)
H170.08670.45260.41300.030*
C180.06699 (15)0.57262 (15)0.39130 (7)0.0181 (5)
C190.18646 (17)0.57902 (15)0.29672 (8)0.0265 (6)
H19A0.18680.58730.26710.040*
H19B0.24290.58840.30750.040*
H19C0.16860.52110.30300.040*
C200.00600 (17)0.77649 (15)0.40344 (7)0.0227 (6)
H20A0.02240.82120.38800.034*
H20B0.03590.73990.41640.034*
H20C0.04160.80200.42450.034*
C210.22608 (17)0.53580 (14)0.42264 (7)0.0206 (5)
C220.16839 (18)0.59961 (15)0.43274 (8)0.0264 (6)
H220.11550.60010.41940.032*
C230.18557 (19)0.66182 (16)0.46131 (8)0.0295 (6)
H230.14470.70390.46710.035*
C240.26167 (19)0.66321 (16)0.48145 (8)0.0307 (6)
H240.27390.70570.50110.037*
C250.31964 (18)0.60072 (15)0.47213 (7)0.0244 (6)
H250.37220.60110.48570.029*
C260.30359 (16)0.53794 (14)0.44382 (7)0.0191 (5)
C270.44191 (16)0.50477 (14)0.42074 (7)0.0205 (5)
C280.51903 (18)0.49602 (16)0.43994 (8)0.0269 (6)
H280.52250.46530.46480.032*
C290.59142 (19)0.53139 (17)0.42340 (9)0.0333 (7)
H290.64370.52420.43680.040*
C300.58688 (19)0.57695 (18)0.38751 (9)0.0348 (7)
H300.63540.60410.37700.042*
C310.51092 (19)0.58309 (15)0.36667 (9)0.0310 (6)
H310.50840.61360.34170.037*
C320.43867 (17)0.54505 (14)0.38190 (8)0.0224 (5)
C330.33363 (17)0.45479 (15)0.35471 (7)0.0212 (5)
C340.38313 (18)0.40175 (16)0.33094 (7)0.0261 (6)
H340.43160.42400.31800.031*
C350.36331 (19)0.31719 (17)0.32570 (8)0.0312 (6)
H350.39680.28210.30870.037*
C360.29458 (19)0.28494 (16)0.34544 (8)0.0311 (6)
H360.28140.22650.34300.037*
C370.24396 (18)0.33734 (15)0.36908 (8)0.0252 (6)
H370.19650.31390.38240.030*
C380.26102 (17)0.42343 (15)0.37376 (7)0.0207 (5)
C390.36655 (18)0.40468 (15)0.46536 (7)0.0243 (6)
H39A0.31060.37920.46650.036*
H39B0.38180.42590.49250.036*
H39C0.40740.36200.45670.036*
C400.3533 (2)0.59413 (17)0.32455 (8)0.0328 (7)
H40A0.39290.57440.30380.049*
H40B0.36550.65320.33140.049*
H40C0.29610.58990.31390.049*
C410.0552 (6)0.3854 (4)0.46578 (13)0.0380 (12)0.790 (8)
H41A0.01620.43080.47440.046*0.790 (8)
H41B0.11320.40360.47190.046*0.790 (8)
C420.0353 (3)0.3049 (4)0.48744 (12)0.0405 (12)0.790 (8)
H42A0.00390.31620.51290.049*0.790 (8)
H42B0.08720.27360.49420.049*0.790 (8)
C430.0177 (3)0.2556 (3)0.45750 (14)0.0388 (11)0.790 (8)
H43A0.01220.19400.46210.047*0.790 (8)
H43B0.07750.27170.45970.047*0.790 (8)
C440.0174 (4)0.2806 (3)0.41696 (15)0.0356 (12)0.790 (8)
H44A0.06480.24340.40930.043*0.790 (8)
H44B0.02600.27710.39540.043*0.790 (8)
C41B0.063 (2)0.4049 (16)0.4631 (5)0.038 (3)0.210 (8)
H41C0.04640.46530.46410.046*0.210 (8)
H41D0.12270.39960.47030.046*0.210 (8)
C42B0.0085 (12)0.3520 (12)0.4910 (4)0.040 (2)0.210 (8)
H42C0.03380.34770.51860.048*0.210 (8)
H42D0.04820.37690.49360.048*0.210 (8)
C43B0.0048 (15)0.2675 (11)0.4709 (6)0.040 (2)0.210 (8)
H43C0.05290.24470.47210.048*0.210 (8)
H43D0.04280.22730.48480.048*0.210 (8)
C44B0.0314 (18)0.2792 (9)0.4274 (5)0.038 (3)0.210 (8)
H44C0.08320.24680.42170.045*0.210 (8)
H44D0.01310.25960.40850.045*0.210 (8)
C450.1079 (2)0.36793 (17)0.29266 (7)0.0310 (7)
H45A0.12740.30860.29040.037*
H45B0.15740.40560.29340.037*
C460.0515 (2)0.39048 (17)0.25683 (8)0.0322 (7)
H46A0.06420.44800.24660.039*
H46B0.05880.34960.23420.039*
C470.0369 (2)0.3863 (2)0.27371 (8)0.0408 (8)
H47A0.06400.44250.27250.049*
H47B0.07110.34540.25800.049*
C480.0273 (2)0.35759 (19)0.31744 (8)0.0374 (7)
H48A0.06820.38690.33520.045*
H48B0.03640.29580.31970.045*
N10.00017 (13)0.54988 (11)0.36630 (6)0.0176 (4)
N20.05762 (14)0.72633 (12)0.37581 (6)0.0194 (4)
N30.12926 (13)0.63808 (11)0.31516 (6)0.0182 (4)
N40.20224 (13)0.47367 (12)0.39503 (6)0.0184 (4)
N50.36636 (14)0.47409 (12)0.43652 (6)0.0192 (4)
N60.36110 (14)0.54189 (12)0.36104 (6)0.0231 (5)
Fe10.08313 (2)0.45812 (2)0.37925 (2)0.01653 (11)
O10.04577 (13)0.36799 (10)0.42238 (5)0.0287 (4)
O20.05724 (12)0.37914 (11)0.32899 (5)0.0272 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0183 (14)0.0122 (10)0.0199 (12)0.0029 (9)0.0020 (10)0.0015 (9)
C20.0200 (15)0.0189 (11)0.0212 (12)0.0012 (10)0.0024 (10)0.0023 (9)
C30.0215 (15)0.0225 (11)0.0238 (13)0.0024 (11)0.0046 (10)0.0007 (10)
C40.0290 (16)0.0240 (12)0.0172 (11)0.0043 (11)0.0014 (10)0.0021 (10)
C50.0253 (15)0.0167 (11)0.0202 (12)0.0013 (10)0.0050 (10)0.0020 (9)
C60.0187 (14)0.0131 (10)0.0209 (12)0.0021 (9)0.0004 (10)0.0033 (9)
C70.0200 (15)0.0211 (11)0.0220 (12)0.0013 (10)0.0006 (10)0.0000 (10)
C80.0245 (16)0.0287 (13)0.0283 (14)0.0004 (11)0.0067 (11)0.0022 (11)
C90.0319 (19)0.0312 (14)0.0435 (17)0.0130 (13)0.0122 (13)0.0004 (12)
C100.045 (2)0.0208 (12)0.0480 (18)0.0117 (13)0.0108 (15)0.0061 (12)
C110.0326 (18)0.0245 (13)0.0344 (15)0.0016 (12)0.0078 (13)0.0062 (11)
C120.0194 (15)0.0224 (12)0.0230 (12)0.0010 (10)0.0004 (10)0.0012 (10)
C130.0176 (14)0.0238 (12)0.0159 (11)0.0032 (10)0.0029 (9)0.0004 (9)
C140.0183 (15)0.0304 (13)0.0238 (13)0.0014 (11)0.0021 (10)0.0058 (11)
C150.0180 (15)0.0432 (15)0.0246 (13)0.0055 (12)0.0062 (11)0.0049 (12)
C160.0231 (16)0.0346 (14)0.0288 (14)0.0081 (12)0.0028 (11)0.0063 (11)
C170.0220 (15)0.0222 (12)0.0299 (13)0.0017 (10)0.0001 (11)0.0064 (10)
C180.0131 (14)0.0226 (11)0.0185 (12)0.0010 (10)0.0027 (9)0.0001 (9)
C190.0186 (15)0.0253 (12)0.0356 (15)0.0028 (11)0.0017 (11)0.0036 (11)
C200.0232 (15)0.0211 (12)0.0237 (13)0.0024 (10)0.0027 (10)0.0006 (10)
C210.0224 (15)0.0201 (11)0.0192 (12)0.0013 (10)0.0010 (10)0.0013 (10)
C220.0200 (15)0.0280 (13)0.0311 (14)0.0033 (11)0.0092 (11)0.0051 (11)
C230.0271 (17)0.0286 (13)0.0330 (14)0.0093 (12)0.0047 (12)0.0085 (11)
C240.0337 (18)0.0279 (13)0.0307 (14)0.0028 (12)0.0056 (12)0.0134 (11)
C250.0204 (15)0.0297 (13)0.0230 (13)0.0007 (11)0.0041 (10)0.0028 (10)
C260.0192 (14)0.0196 (11)0.0184 (11)0.0009 (10)0.0022 (9)0.0006 (9)
C270.0178 (14)0.0192 (11)0.0245 (13)0.0010 (10)0.0041 (10)0.0058 (10)
C280.0255 (16)0.0300 (13)0.0252 (13)0.0030 (11)0.0007 (11)0.0105 (11)
C290.0183 (16)0.0388 (15)0.0428 (16)0.0010 (12)0.0025 (12)0.0202 (13)
C300.0248 (17)0.0324 (14)0.0473 (17)0.0103 (13)0.0118 (13)0.0127 (13)
C310.0358 (19)0.0219 (12)0.0351 (15)0.0038 (12)0.0124 (13)0.0030 (11)
C320.0233 (15)0.0164 (11)0.0274 (13)0.0021 (10)0.0073 (11)0.0048 (10)
C330.0271 (16)0.0224 (12)0.0142 (11)0.0056 (11)0.0040 (10)0.0014 (9)
C340.0258 (16)0.0316 (13)0.0208 (12)0.0042 (12)0.0025 (11)0.0022 (10)
C350.0303 (18)0.0332 (14)0.0301 (14)0.0117 (13)0.0054 (12)0.0118 (12)
C360.0275 (17)0.0230 (13)0.0430 (16)0.0034 (11)0.0079 (13)0.0121 (12)
C370.0172 (14)0.0246 (13)0.0339 (14)0.0017 (11)0.0047 (11)0.0044 (11)
C380.0198 (14)0.0229 (12)0.0195 (12)0.0061 (10)0.0063 (10)0.0032 (10)
C390.0245 (16)0.0252 (12)0.0232 (13)0.0057 (11)0.0027 (11)0.0020 (10)
C400.0338 (18)0.0329 (14)0.0316 (15)0.0056 (12)0.0033 (12)0.0116 (12)
C410.056 (3)0.038 (3)0.0193 (19)0.005 (2)0.0013 (19)0.0042 (18)
C420.045 (3)0.047 (3)0.0293 (19)0.012 (2)0.0061 (17)0.0139 (19)
C430.042 (3)0.044 (2)0.030 (2)0.0157 (19)0.0056 (18)0.0096 (18)
C440.053 (3)0.0231 (17)0.031 (2)0.0130 (17)0.002 (2)0.0099 (16)
C41B0.048 (5)0.045 (5)0.021 (5)0.006 (5)0.002 (4)0.016 (4)
C42B0.047 (5)0.045 (5)0.028 (4)0.009 (4)0.003 (4)0.010 (4)
C43B0.049 (5)0.040 (4)0.031 (5)0.009 (4)0.002 (4)0.013 (4)
C44B0.050 (5)0.036 (5)0.028 (5)0.000 (4)0.005 (5)0.014 (4)
C450.041 (2)0.0278 (13)0.0241 (13)0.0064 (12)0.0021 (12)0.0067 (11)
C460.0403 (19)0.0287 (13)0.0277 (14)0.0020 (12)0.0069 (12)0.0015 (11)
C470.047 (2)0.0438 (16)0.0322 (15)0.0122 (15)0.0095 (14)0.0108 (13)
C480.0323 (19)0.0430 (16)0.0369 (16)0.0113 (14)0.0083 (13)0.0070 (13)
N10.0148 (11)0.0189 (9)0.0189 (9)0.0010 (8)0.0010 (8)0.0041 (8)
N20.0216 (12)0.0185 (9)0.0180 (10)0.0009 (8)0.0027 (8)0.0007 (8)
N30.0170 (12)0.0162 (9)0.0215 (10)0.0005 (8)0.0035 (8)0.0012 (8)
N40.0136 (12)0.0175 (9)0.0242 (10)0.0030 (8)0.0037 (8)0.0020 (8)
N50.0173 (12)0.0210 (9)0.0193 (10)0.0014 (8)0.0009 (8)0.0003 (8)
N60.0270 (13)0.0207 (10)0.0217 (10)0.0014 (9)0.0017 (9)0.0020 (8)
Fe10.0167 (2)0.01553 (17)0.01733 (19)0.00079 (15)0.00282 (15)0.00016 (15)
O10.0407 (13)0.0233 (8)0.0220 (9)0.0009 (8)0.0016 (8)0.0036 (7)
O20.0302 (12)0.0271 (9)0.0242 (9)0.0020 (8)0.0053 (8)0.0073 (7)
Geometric parameters (Å, º) top
C1—N11.394 (3)C31—H310.9500
C1—C61.411 (3)C32—N61.415 (4)
C1—C21.416 (4)C33—C341.390 (4)
C2—C31.378 (3)C33—C381.406 (4)
C2—H20.9500C33—N61.460 (3)
C3—C41.384 (4)C34—C351.384 (4)
C3—H30.9500C34—H340.9500
C4—C51.397 (4)C35—C361.372 (4)
C4—H40.9500C35—H350.9500
C5—C61.388 (3)C36—C371.392 (4)
C5—H50.9500C36—H360.9500
C6—N31.444 (3)C37—C381.396 (3)
C7—C81.387 (4)C37—H370.9500
C7—N31.415 (3)C38—N41.413 (3)
C7—C121.418 (3)C39—N51.448 (3)
C8—C91.397 (4)C39—H39A0.9800
C8—H80.9500C39—H39B0.9800
C9—C101.384 (4)C39—H39C0.9800
C9—H90.9500C40—N61.458 (3)
C10—C111.386 (4)C40—H40A0.9800
C10—H100.9500C40—H40B0.9800
C11—C121.384 (4)C40—H40C0.9800
C11—H110.9500C41—O11.455 (5)
C12—N21.415 (3)C41—C421.490 (6)
C13—C141.388 (4)C41—H41A0.9900
C13—C181.411 (3)C41—H41B0.9900
C13—N21.448 (3)C42—C431.512 (6)
C14—C151.386 (4)C42—H42A0.9900
C14—H140.9500C42—H42B0.9900
C15—C161.377 (4)C43—C441.495 (5)
C15—H150.9500C43—H43A0.9900
C16—C171.383 (4)C43—H43B0.9900
C16—H160.9500C44—O11.464 (4)
C17—C181.414 (3)C44—H44A0.9900
C17—H170.9500C44—H44B0.9900
C18—N11.396 (3)C41B—O11.479 (14)
C19—N31.439 (3)C41B—C42B1.512 (17)
C19—H19A0.9800C41B—H41C0.9900
C19—H19B0.9800C41B—H41D0.9900
C19—H19C0.9800C42B—C43B1.492 (16)
C20—N21.458 (3)C42B—H42C0.9900
C20—H20A0.9800C42B—H42D0.9900
C20—H20B0.9800C43B—C44B1.497 (15)
C20—H20C0.9800C43B—H43C0.9900
C21—N41.388 (3)C43B—H43D0.9900
C21—C221.405 (4)C44B—O11.431 (14)
C21—C261.419 (4)C44B—H44C0.9900
C22—C231.385 (3)C44B—H44D0.9900
C22—H220.9500C45—O21.449 (3)
C23—C241.382 (4)C45—C461.522 (4)
C23—H230.9500C45—H45A0.9900
C24—C251.387 (4)C45—H45B0.9900
C24—H240.9500C46—C471.516 (5)
C25—C261.382 (3)C46—H46A0.9900
C25—H250.9500C46—H46B0.9900
C26—N51.442 (3)C47—C481.510 (4)
C27—C281.389 (4)C47—H47A0.9900
C27—N51.399 (3)C47—H47B0.9900
C27—C321.423 (4)C48—O21.442 (3)
C28—C291.393 (4)C48—H48A0.9900
C28—H280.9500C48—H48B0.9900
C29—C301.380 (4)N1—Fe12.0092 (19)
C29—H290.9500N4—Fe11.985 (2)
C30—C311.395 (4)Fe1—O12.0926 (17)
C30—H300.9500Fe1—O22.1068 (16)
C31—C321.393 (4)
N1—C1—C6126.7 (2)C33—C38—N4124.6 (2)
N1—C1—C2117.2 (2)N5—C39—H39A109.5
C6—C1—C2116.0 (2)N5—C39—H39B109.5
C3—C2—C1122.8 (2)H39A—C39—H39B109.5
C3—C2—H2118.6N5—C39—H39C109.5
C1—C2—H2118.6H39A—C39—H39C109.5
C2—C3—C4120.6 (3)H39B—C39—H39C109.5
C2—C3—H3119.7N6—C40—H40A109.5
C4—C3—H3119.7N6—C40—H40B109.5
C3—C4—C5117.7 (2)H40A—C40—H40B109.5
C3—C4—H4121.1N6—C40—H40C109.5
C5—C4—H4121.1H40A—C40—H40C109.5
C6—C5—C4122.3 (2)H40B—C40—H40C109.5
C6—C5—H5118.8O1—C41—C42106.3 (3)
C4—C5—H5118.8O1—C41—H41A110.5
C5—C6—C1120.4 (2)C42—C41—H41A110.5
C5—C6—N3118.0 (2)O1—C41—H41B110.5
C1—C6—N3121.6 (2)C42—C41—H41B110.5
C8—C7—N3124.2 (2)H41A—C41—H41B108.7
C8—C7—C12119.5 (2)C41—C42—C43104.5 (4)
N3—C7—C12116.3 (2)C41—C42—H42A110.9
C7—C8—C9120.5 (3)C43—C42—H42A110.9
C7—C8—H8119.7C41—C42—H42B110.9
C9—C8—H8119.7C43—C42—H42B110.9
C10—C9—C8119.4 (3)H42A—C42—H42B108.9
C10—C9—H9120.3C44—C43—C42103.3 (3)
C8—C9—H9120.3C44—C43—H43A111.1
C9—C10—C11120.7 (2)C42—C43—H43A111.1
C9—C10—H10119.7C44—C43—H43B111.1
C11—C10—H10119.7C42—C43—H43B111.1
C12—C11—C10120.5 (3)H43A—C43—H43B109.1
C12—C11—H11119.8O1—C44—C43104.9 (3)
C10—C11—H11119.8O1—C44—H44A110.8
C11—C12—N2124.1 (2)C43—C44—H44A110.8
C11—C12—C7119.2 (2)O1—C44—H44B110.8
N2—C12—C7116.7 (2)C43—C44—H44B110.8
C14—C13—C18120.5 (2)H44A—C44—H44B108.8
C14—C13—N2118.6 (2)O1—C41B—C42B102.9 (12)
C18—C13—N2120.8 (2)O1—C41B—H41C111.2
C15—C14—C13121.7 (2)C42B—C41B—H41C111.2
C15—C14—H14119.1O1—C41B—H41D111.2
C13—C14—H14119.1C42B—C41B—H41D111.2
C16—C15—C14118.8 (2)H41C—C41B—H41D109.1
C16—C15—H15120.6C43B—C42B—C41B104.4 (13)
C14—C15—H15120.6C43B—C42B—H42C110.9
C15—C16—C17120.4 (2)C41B—C42B—H42C110.9
C15—C16—H16119.8C43B—C42B—H42D110.9
C17—C16—H16119.8C41B—C42B—H42D110.9
C16—C17—C18122.3 (2)H42C—C42B—H42D108.9
C16—C17—H17118.9C42B—C43B—C44B107.4 (12)
C18—C17—H17118.9C42B—C43B—H43C110.2
N1—C18—C13124.9 (2)C44B—C43B—H43C110.2
N1—C18—C17118.7 (2)C42B—C43B—H43D110.2
C13—C18—C17116.3 (2)C44B—C43B—H43D110.2
N3—C19—H19A109.5H43C—C43B—H43D108.5
N3—C19—H19B109.5O1—C44B—C43B106.0 (12)
H19A—C19—H19B109.5O1—C44B—H44C110.5
N3—C19—H19C109.5C43B—C44B—H44C110.5
H19A—C19—H19C109.5O1—C44B—H44D110.5
H19B—C19—H19C109.5C43B—C44B—H44D110.5
N2—C20—H20A109.5H44C—C44B—H44D108.7
N2—C20—H20B109.5O2—C45—C46105.9 (2)
H20A—C20—H20B109.5O2—C45—H45A110.6
N2—C20—H20C109.5C46—C45—H45A110.6
H20A—C20—H20C109.5O2—C45—H45B110.6
H20B—C20—H20C109.5C46—C45—H45B110.6
N4—C21—C22118.8 (2)H45A—C45—H45B108.7
N4—C21—C26125.1 (2)C47—C46—C45105.0 (2)
C22—C21—C26116.1 (2)C47—C46—H46A110.7
C23—C22—C21122.6 (3)C45—C46—H46A110.7
C23—C22—H22118.7C47—C46—H46B110.7
C21—C22—H22118.7C45—C46—H46B110.7
C24—C23—C22120.5 (2)H46A—C46—H46B108.8
C24—C23—H23119.7C48—C47—C46105.4 (3)
C22—C23—H23119.7C48—C47—H47A110.7
C23—C24—C25118.0 (2)C46—C47—H47A110.7
C23—C24—H24121.0C48—C47—H47B110.7
C25—C24—H24121.0C46—C47—H47B110.7
C26—C25—C24122.4 (3)H47A—C47—H47B108.8
C26—C25—H25118.8O2—C48—C47105.8 (2)
C24—C25—H25118.8O2—C48—H48A110.6
C25—C26—C21120.5 (2)C47—C48—H48A110.6
C25—C26—N5119.0 (2)O2—C48—H48B110.6
C21—C26—N5120.5 (2)C47—C48—H48B110.6
C28—C27—N5124.2 (2)H48A—C48—H48B108.7
C28—C27—C32118.8 (2)C1—N1—C18122.71 (19)
N5—C27—C32117.0 (2)C1—N1—Fe1112.67 (16)
C27—C28—C29121.3 (3)C18—N1—Fe1124.62 (15)
C27—C28—H28119.4C12—N2—C13112.8 (2)
C29—C28—H28119.4C12—N2—C20117.01 (19)
C30—C29—C28119.8 (3)C13—N2—C20111.86 (17)
C30—C29—H29120.1C7—N3—C19118.6 (2)
C28—C29—H29120.1C7—N3—C6113.33 (19)
C29—C30—C31119.9 (3)C19—N3—C6115.48 (19)
C29—C30—H30120.0C21—N4—C38122.4 (2)
C31—C30—H30120.0C21—N4—Fe1121.30 (16)
C32—C31—C30121.0 (3)C38—N4—Fe1115.99 (15)
C32—C31—H31119.5C27—N5—C26114.68 (19)
C30—C31—H31119.5C27—N5—C39120.1 (2)
C31—C32—N6124.5 (2)C26—N5—C39115.07 (19)
C31—C32—C27118.9 (3)C32—N6—C40116.8 (2)
N6—C32—C27116.6 (2)C32—N6—C33111.40 (19)
C34—C33—C38120.3 (2)C40—N6—C33113.1 (2)
C34—C33—N6118.5 (2)N4—Fe1—N1126.64 (8)
C38—C33—N6121.1 (2)N4—Fe1—O1100.46 (8)
C35—C34—C33121.5 (3)N1—Fe1—O1116.49 (8)
C35—C34—H34119.3N4—Fe1—O2117.67 (8)
C33—C34—H34119.3N1—Fe1—O297.67 (8)
C36—C35—C34118.9 (3)O1—Fe1—O293.90 (7)
C36—C35—H35120.6C41—O1—C44109.2 (3)
C34—C35—H35120.6C44B—O1—C41B108.2 (11)
C35—C36—C37120.3 (2)C44B—O1—Fe1142.2 (8)
C35—C36—H36119.8C41—O1—Fe1120.1 (2)
C37—C36—H36119.8C44—O1—Fe1130.4 (2)
C36—C37—C38121.8 (3)C41B—O1—Fe1106.7 (7)
C36—C37—H37119.1C48—O2—C45106.1 (2)
C38—C37—H37119.1C48—O2—Fe1121.89 (17)
C37—C38—C33117.1 (2)C45—O2—Fe1127.18 (16)
C37—C38—N4118.2 (2)
N1—C1—C2—C3172.5 (2)C42—C43—C44—O132.1 (5)
C6—C1—C2—C33.5 (3)O1—C41B—C42B—C43B30 (3)
C1—C2—C3—C42.7 (4)C41B—C42B—C43B—C44B18 (3)
C2—C3—C4—C50.0 (3)C42B—C43B—C44B—O13 (2)
C3—C4—C5—C61.9 (3)O2—C45—C46—C4717.9 (3)
C4—C5—C6—C11.0 (3)C45—C46—C47—C482.7 (3)
C4—C5—C6—N3177.8 (2)C46—C47—C48—O222.5 (3)
N1—C1—C6—C5173.9 (2)C6—C1—N1—C1827.5 (3)
C2—C1—C6—C51.6 (3)C2—C1—N1—C18157.1 (2)
N1—C1—C6—N34.8 (3)C6—C1—N1—Fe1152.43 (18)
C2—C1—C6—N3179.66 (19)C2—C1—N1—Fe123.0 (2)
N3—C7—C8—C9177.5 (3)C13—C18—N1—C136.1 (3)
C12—C7—C8—C92.7 (4)C17—C18—N1—C1147.9 (2)
C7—C8—C9—C101.2 (5)C13—C18—N1—Fe1144.0 (2)
C8—C9—C10—C112.7 (5)C17—C18—N1—Fe131.9 (3)
C9—C10—C11—C120.2 (5)C11—C12—N2—C13122.2 (3)
C10—C11—C12—N2175.6 (3)C7—C12—N2—C1357.1 (3)
C10—C11—C12—C73.7 (4)C11—C12—N2—C209.6 (4)
C8—C7—C12—C115.2 (4)C7—C12—N2—C20171.1 (2)
N3—C7—C12—C11175.0 (2)C14—C13—N2—C1261.2 (3)
C8—C7—C12—N2174.2 (2)C18—C13—N2—C12121.1 (2)
N3—C7—C12—N25.6 (3)C14—C13—N2—C2073.2 (3)
C18—C13—C14—C152.5 (4)C18—C13—N2—C20104.5 (3)
N2—C13—C14—C15175.2 (2)C8—C7—N3—C1923.0 (4)
C13—C14—C15—C160.7 (4)C12—C7—N3—C19156.8 (2)
C14—C15—C16—C170.9 (4)C8—C7—N3—C6117.2 (3)
C15—C16—C17—C180.9 (4)C12—C7—N3—C663.0 (3)
C14—C13—C18—N1178.5 (2)C5—C6—N3—C764.9 (3)
N2—C13—C18—N10.8 (4)C1—C6—N3—C7116.4 (2)
C14—C13—C18—C172.4 (3)C5—C6—N3—C1976.6 (3)
N2—C13—C18—C17175.2 (2)C1—C6—N3—C19102.2 (2)
C16—C17—C18—N1177.1 (2)C22—C21—N4—C38160.3 (2)
C16—C17—C18—C130.8 (4)C26—C21—N4—C3823.6 (4)
N4—C21—C22—C23177.1 (2)C22—C21—N4—Fe113.7 (3)
C26—C21—C22—C230.6 (4)C26—C21—N4—Fe1162.43 (19)
C21—C22—C23—C240.2 (4)C37—C38—N4—C21139.0 (2)
C22—C23—C24—C250.0 (4)C33—C38—N4—C2145.0 (3)
C23—C24—C25—C260.2 (4)C37—C38—N4—Fe146.7 (3)
C24—C25—C26—C210.6 (4)C33—C38—N4—Fe1129.3 (2)
C24—C25—C26—N5178.6 (2)C28—C27—N5—C26120.0 (2)
N4—C21—C26—C25177.0 (2)C32—C27—N5—C2662.0 (3)
C22—C21—C26—C250.8 (3)C28—C27—N5—C3923.7 (3)
N4—C21—C26—N52.2 (4)C32—C27—N5—C39154.3 (2)
C22—C21—C26—N5178.4 (2)C25—C26—N5—C2762.8 (3)
N5—C27—C28—C29177.1 (2)C21—C26—N5—C27118.0 (2)
C32—C27—C28—C294.9 (3)C25—C26—N5—C3982.8 (3)
C27—C28—C29—C300.8 (4)C21—C26—N5—C3996.4 (3)
C28—C29—C30—C313.9 (4)C31—C32—N6—C4010.8 (3)
C29—C30—C31—C321.2 (4)C27—C32—N6—C40170.5 (2)
C30—C31—C32—N6174.2 (2)C31—C32—N6—C33121.3 (2)
C30—C31—C32—C274.5 (4)C27—C32—N6—C3357.5 (3)
C28—C27—C32—C317.5 (3)C34—C33—N6—C3262.3 (3)
N5—C27—C32—C31174.4 (2)C38—C33—N6—C32114.5 (3)
C28—C27—C32—N6171.4 (2)C34—C33—N6—C4071.6 (3)
N5—C27—C32—N66.7 (3)C38—C33—N6—C40111.6 (3)
C38—C33—C34—C350.7 (4)C43B—C44B—O1—C41B23 (3)
N6—C33—C34—C35176.1 (2)C43B—C44B—O1—Fe1179.4 (10)
C33—C34—C35—C361.9 (4)C42—C41—O1—C442.4 (8)
C34—C35—C36—C372.4 (4)C42—C41—O1—Fe1171.7 (4)
C35—C36—C37—C380.3 (4)C43—C44—O1—C4118.9 (6)
C36—C37—C38—C332.3 (4)C43—C44—O1—Fe1167.9 (2)
C36—C37—C38—N4174.1 (2)C42B—C41B—O1—C44B34 (3)
C34—C33—C38—C372.7 (4)C42B—C41B—O1—Fe1161.2 (16)
N6—C33—C38—C37174.0 (2)C47—C48—O2—C4534.6 (3)
C34—C33—C38—N4173.3 (2)C47—C48—O2—Fe1122.5 (2)
N6—C33—C38—N49.9 (4)C46—C45—O2—C4832.7 (3)
O1—C41—C42—C4322.4 (7)C46—C45—O2—Fe1122.7 (2)
C41—C42—C43—C4433.5 (6)
Selected bond lengths (Å) and angles (°) for 9 and 10a top
910
Fe1—N42.153 (4)N4—Fe1—N789.8 (1)Fe1—N12.009 (2)
Fe1—N72.091 (3)N4—Fe1—N9122.6 (1)Fe1—N41.986 (2)
Fe1—N91.992 (4)N4—Fe1—N10115.7 (1)Fe1—O12.093 (2)
Fe1—N102.245 (3)N7—Fe1—N979.8 (1)Fe1—O22.107 (2)
N7—Fe1—N10139.6 (1)
Fe2—N11.947 (4)N9—Fe1—N10107.5 (1)N1—Fe1—N4126.64 (8)
Fe2—N42.068 (3)O1—Fe1—O293.90 (7)
Fe2—N72.061 (4)N1—Fe2—N4143.6 (2)N1–Fe1–O1116.48 (8)
N1—Fe2—N7123.2 (2)N1—Fe1—O297.67 (8)
Fe1···Fe22.912 (1)N4—Fe2—N793.0 (1)N4—Fe1—O1100.46 (8)
Fe2···C212.425 (4)N4—Fe1—O2117.68 (8)
Fe2···C383.181 (5)
Note: (a) numbers in parentheses are standard uncertainties in the last significant figures. Atoms are labeled as indicated in Figs. 5 and 7.
Bond orders for the Fe—Fe and all the Fe—N bonds in 9 top
EntryAtom 1Atom 2Bond Order
1Fe1Fe2-0.113
2Fe1N40.342
3Fe1N70.296
4Fe1N90.253
5Fe1N100.564
6Fe2N10.556
7Fe2N40.303
8Fe2N70.383
 

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