research papers
Typically reactions of N-heterocyclic carbenes with transition metals are straightforward and require a carbene salt, a base strong enough to deprotonate such a salt and a metal. Yet when carbene precursors are in the form of triazolium salts, reaction may not proceed as easily as expected. In our work, we intended to obtain a triazolylidene complex of iron(II) chloride, but due to the presence of small amounts of water in the tetrahydrofuran solvent used, bis(acetonitrile)tetrakis(1-benzyl-1H-1,2,4-triazole-κN4)iron(II) μ-oxido-bis[trichloridoferrate(III)] acetonitrile disolvate, [Fe(C9H9N3)4(CH3CN)2][Fe2Cl6O]·2CH3CN – an interesting anion with a linear geometry of the O atom – was formed instead of the iron carbene complex. Reaction proceeded via cleavage of the alkyl N-substituent of the triazolium salt. The formation of the product was confirmed by X-ray crystallography. The crystal structure and possible reaction pathways are discussed.
Keywords: crystal structure; triazole; imine; hexachloridooxidodiferrate anion; iron complex; N-heterocyclic carbene; organometallic chemistry.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624002973/oj3018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002973/oj3018Isup2.hkl |
CCDC reference: 2324408
Computing details top
Bis(acetonitrile)tetrakis(1-benzyl-1H-1,2,4-triazole-κN4)iron(II) µ-oxido-bis[trichloridoferrate(III)] acetonitrile disolvate top
Crystal data top
[Fe(C9H9N3)4(C2H3N)2][Fe2Cl6O]·2C2H3N | Z = 1 |
Mr = 1197.23 | F(000) = 612 |
Triclinic, P1 | Dx = 1.496 Mg m−3 |
a = 8.9568 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 12.8555 (4) Å | Cell parameters from 9907 reflections |
c = 12.8951 (5) Å | θ = 3.8–70.6° |
α = 116.349 (4)° | µ = 9.67 mm−1 |
β = 91.178 (3)° | T = 120 K |
γ = 91.622 (3)° | Block, red |
V = 1329.09 (9) Å3 | 0.16 × 0.11 × 0.08 mm |
Data collection top
Agilent SuperNova Dual source diffractometer with an Atlas detector | 5052 independent reflections |
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source | 4520 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 5.2195 pixels mm-1 | θmax = 70.8°, θmin = 3.8° |
ω scans | h = −10→9 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | k = −15→15 |
Tmin = 0.618, Tmax = 0.755 | l = −15→15 |
20380 measured reflections |
Refinement top
Refinement on F2 | 48 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.080 | H-atom parameters constrained |
wR(F2) = 0.238 | w = 1/[σ2(Fo2) + (0.1515P)2 + 2.6594P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.005 |
5052 reflections | Δρmax = 1.39 e Å−3 |
328 parameters | Δρmin = −0.96 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | −0.0865 (5) | 0.0122 (4) | 0.2556 (4) | 0.0395 (10) | |
C2 | −0.1286 (6) | 0.0155 (7) | 0.3654 (5) | 0.0632 (17) | |
H2A | −0.2378 | 0.0123 | 0.3683 | 0.095* | |
H2B | −0.0881 | 0.0875 | 0.4293 | 0.095* | |
H2C | −0.0884 | −0.0513 | 0.3724 | 0.095* | |
C3 | −0.2015 (5) | 0.1852 (4) | −0.0249 (4) | 0.0380 (9) | |
H3 | −0.2195 | 0.1378 | −0.1055 | 0.046* | |
C4 | −0.1266 (6) | 0.2502 (4) | 0.1484 (4) | 0.0465 (11) | |
H4 | −0.0768 | 0.2560 | 0.2166 | 0.056* | |
C5 | 0.3342 (7) | 0.1029 (6) | 0.0213 (6) | 0.0598 (14) | |
H5 | 0.3393 | 0.0643 | −0.0606 | 0.072* | |
C6 | 0.2520 (7) | 0.1631 (5) | 0.1863 (5) | 0.0570 (14) | |
H6 | 0.1912 | 0.1791 | 0.2507 | 0.068* | |
C7 | −0.3603 (6) | 0.3516 (4) | −0.0042 (5) | 0.0446 (11) | |
H7A | −0.4543 | 0.3623 | 0.0377 | 0.054* | |
H7B | −0.3847 | 0.3050 | −0.0879 | 0.054* | |
C8 | −0.2942 (6) | 0.4683 (4) | 0.0164 (5) | 0.0455 (11) | |
C9A | −0.169 (3) | 0.4764 (19) | −0.0449 (16) | 0.061 (5) | 0.47 (4) |
H9A | −0.1273 | 0.4067 | −0.0989 | 0.073* | 0.47 (4) |
C10A | −0.104 (3) | 0.5827 (19) | −0.0294 (16) | 0.072 (4) | 0.47 (4) |
H10A | −0.0191 | 0.5876 | −0.0705 | 0.087* | 0.47 (4) |
C9B | −0.239 (3) | 0.4812 (13) | −0.076 (2) | 0.066 (5) | 0.53 (4) |
H9B | −0.2414 | 0.4169 | −0.1506 | 0.079* | 0.53 (4) |
C10B | −0.179 (3) | 0.5884 (16) | −0.060 (3) | 0.092 (8) | 0.53 (4) |
H10B | −0.1423 | 0.5983 | −0.1242 | 0.110* | 0.53 (4) |
C11 | −0.1725 (10) | 0.6822 (7) | 0.0517 (10) | 0.091 (2) | |
H11 | −0.1584 | 0.7546 | 0.0493 | 0.109* | |
C12 | −0.2596 (9) | 0.6738 (6) | 0.1337 (9) | 0.088 (2) | |
H12 | −0.2782 | 0.7409 | 0.2030 | 0.105* | |
C13 | −0.3202 (8) | 0.5665 (5) | 0.1144 (7) | 0.0702 (17) | |
H13 | −0.3817 | 0.5610 | 0.1711 | 0.084* | |
C14 | 0.4840 (9) | 0.2748 (7) | 0.2976 (7) | 0.086 (2) | |
H14A | 0.5872 | 0.2473 | 0.2874 | 0.103* | |
H14B | 0.4431 | 0.2669 | 0.3646 | 0.103* | |
C15 | 0.4865 (9) | 0.3973 (5) | 0.3206 (7) | 0.113 (2) | |
C16 | 0.6060 (7) | 0.4674 (6) | 0.3885 (7) | 0.115 (3) | |
H16 | 0.6841 | 0.4343 | 0.4135 | 0.139* | |
C17 | 0.6114 (8) | 0.5858 (5) | 0.4200 (7) | 0.125 (3) | |
H17 | 0.6931 | 0.6337 | 0.4665 | 0.151* | |
C18 | 0.4972 (10) | 0.6342 (5) | 0.3835 (7) | 0.117 (2) | |
H18 | 0.5008 | 0.7152 | 0.4050 | 0.141* | |
C19 | 0.3776 (8) | 0.5642 (7) | 0.3155 (7) | 0.142 (4) | |
H19 | 0.2995 | 0.5973 | 0.2906 | 0.170* | |
C20 | 0.3722 (8) | 0.4458 (6) | 0.2841 (7) | 0.135 (3) | |
H20 | 0.2905 | 0.3979 | 0.2376 | 0.162* | |
C21 | 0.9801 (13) | 0.5905 (9) | 0.3572 (7) | 0.109 (3) | |
H21A | 0.8790 | 0.6075 | 0.3403 | 0.164* | |
H21B | 0.9922 | 0.5064 | 0.3186 | 0.164* | |
H21C | 1.0534 | 0.6288 | 0.3287 | 0.164* | |
C22 | 1.0033 (11) | 0.6334 (7) | 0.4818 (7) | 0.087 (2) | |
N1 | −0.0553 (4) | 0.0083 (3) | 0.1691 (3) | 0.0384 (8) | |
N2 | 0.2079 (4) | 0.0980 (3) | 0.0779 (3) | 0.0381 (8) | |
N3 | 0.4485 (6) | 0.1657 (5) | 0.0895 (5) | 0.0684 (14) | |
N4 | 0.3935 (6) | 0.2042 (5) | 0.1946 (5) | 0.0619 (13) | |
N5 | −0.1165 (4) | 0.1573 (3) | 0.0442 (3) | 0.0350 (8) | |
N6 | −0.2107 (6) | 0.3320 (4) | 0.1477 (4) | 0.0500 (10) | |
N7 | −0.2572 (4) | 0.2882 (3) | 0.0346 (3) | 0.0378 (8) | |
N8 | 1.0162 (16) | 0.6712 (8) | 0.5788 (7) | 0.162 (6) | |
O1 | 0.5000 | 0.0000 | 0.5000 | 0.102 (3) | |
Cl1 | 0.50344 (15) | 0.02759 (16) | 0.76172 (13) | 0.0665 (4) | |
Cl2 | 0.7857 (3) | 0.16800 (14) | 0.67204 (14) | 0.0819 (6) | |
Cl3 | 0.76743 (18) | −0.13870 (15) | 0.54232 (16) | 0.0704 (5) | |
Fe1 | 0.0000 | 0.0000 | 0.0000 | 0.0316 (3) | |
Fe2 | 0.62671 (9) | 0.01362 (7) | 0.60932 (7) | 0.0482 (3) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.035 (2) | 0.053 (3) | 0.036 (2) | −0.0075 (18) | −0.0071 (17) | 0.025 (2) |
C2 | 0.046 (3) | 0.119 (5) | 0.040 (3) | −0.010 (3) | −0.003 (2) | 0.050 (3) |
C3 | 0.043 (2) | 0.039 (2) | 0.035 (2) | −0.0040 (18) | −0.0079 (18) | 0.0196 (18) |
C4 | 0.068 (3) | 0.036 (2) | 0.036 (2) | −0.008 (2) | −0.016 (2) | 0.0176 (19) |
C5 | 0.054 (3) | 0.067 (3) | 0.063 (3) | −0.014 (3) | −0.005 (3) | 0.034 (3) |
C6 | 0.059 (3) | 0.061 (3) | 0.054 (3) | −0.021 (3) | −0.017 (3) | 0.031 (3) |
C7 | 0.043 (3) | 0.045 (2) | 0.054 (3) | −0.006 (2) | −0.012 (2) | 0.030 (2) |
C8 | 0.048 (3) | 0.044 (2) | 0.052 (3) | −0.005 (2) | −0.013 (2) | 0.029 (2) |
C9A | 0.060 (11) | 0.069 (9) | 0.063 (9) | −0.024 (8) | −0.013 (8) | 0.040 (8) |
C10A | 0.050 (9) | 0.094 (6) | 0.087 (9) | −0.032 (4) | −0.027 (6) | 0.056 (5) |
C9B | 0.087 (14) | 0.055 (7) | 0.074 (10) | 0.000 (7) | 0.009 (10) | 0.045 (7) |
C10B | 0.080 (16) | 0.096 (11) | 0.141 (17) | −0.014 (9) | 0.008 (14) | 0.091 (12) |
C11 | 0.089 (5) | 0.060 (3) | 0.142 (7) | −0.022 (3) | −0.025 (4) | 0.064 (4) |
C12 | 0.083 (5) | 0.045 (3) | 0.122 (7) | −0.009 (3) | −0.015 (5) | 0.027 (4) |
C13 | 0.076 (4) | 0.048 (3) | 0.076 (4) | −0.008 (3) | 0.002 (3) | 0.019 (3) |
C14 | 0.079 (5) | 0.093 (5) | 0.087 (5) | −0.041 (4) | −0.035 (4) | 0.045 (4) |
C15 | 0.125 (4) | 0.099 (4) | 0.110 (5) | −0.029 (2) | −0.039 (3) | 0.045 (3) |
C16 | 0.099 (4) | 0.096 (2) | 0.120 (6) | −0.023 (4) | −0.009 (4) | 0.021 (4) |
C17 | 0.100 (5) | 0.109 (2) | 0.164 (7) | −0.026 (3) | −0.017 (4) | 0.061 (3) |
C18 | 0.135 (4) | 0.105 (5) | 0.110 (5) | −0.005 (3) | −0.004 (3) | 0.047 (3) |
C19 | 0.133 (5) | 0.118 (6) | 0.167 (8) | −0.023 (4) | −0.008 (4) | 0.059 (5) |
C20 | 0.142 (5) | 0.106 (5) | 0.160 (6) | 0.010 (3) | −0.013 (4) | 0.063 (4) |
C21 | 0.131 (8) | 0.107 (7) | 0.054 (4) | −0.030 (6) | −0.002 (5) | 0.005 (4) |
C22 | 0.107 (5) | 0.076 (4) | 0.064 (4) | 0.013 (4) | −0.018 (4) | 0.018 (3) |
N1 | 0.043 (2) | 0.047 (2) | 0.0312 (19) | −0.0060 (16) | −0.0073 (15) | 0.0233 (16) |
N2 | 0.043 (2) | 0.0412 (19) | 0.0365 (19) | −0.0076 (15) | −0.0071 (15) | 0.0242 (16) |
N3 | 0.056 (3) | 0.081 (4) | 0.078 (4) | −0.022 (3) | −0.005 (3) | 0.046 (3) |
N4 | 0.063 (3) | 0.071 (3) | 0.059 (3) | −0.026 (2) | −0.018 (2) | 0.037 (2) |
N5 | 0.043 (2) | 0.0356 (18) | 0.0288 (17) | −0.0082 (15) | −0.0074 (14) | 0.0176 (14) |
N6 | 0.074 (3) | 0.039 (2) | 0.036 (2) | −0.0052 (19) | −0.0122 (19) | 0.0166 (17) |
N7 | 0.044 (2) | 0.0362 (18) | 0.0368 (19) | −0.0101 (15) | −0.0120 (15) | 0.0207 (15) |
N8 | 0.278 (15) | 0.104 (6) | 0.067 (5) | 0.077 (8) | −0.063 (7) | 0.004 (4) |
O1 | 0.094 (5) | 0.149 (8) | 0.056 (4) | 0.041 (5) | −0.025 (4) | 0.038 (4) |
Cl1 | 0.0441 (7) | 0.1045 (12) | 0.0621 (8) | −0.0075 (7) | −0.0052 (6) | 0.0479 (8) |
Cl2 | 0.1198 (15) | 0.0610 (9) | 0.0535 (8) | −0.0267 (9) | 0.0142 (9) | 0.0164 (7) |
Cl3 | 0.0642 (9) | 0.0727 (9) | 0.0908 (11) | 0.0115 (7) | 0.0148 (8) | 0.0504 (9) |
Fe1 | 0.0381 (5) | 0.0359 (5) | 0.0261 (5) | −0.0052 (4) | −0.0051 (3) | 0.0193 (4) |
Fe2 | 0.0506 (5) | 0.0567 (5) | 0.0406 (5) | −0.0018 (4) | −0.0114 (3) | 0.0255 (4) |
Geometric parameters (Å, º) top
C1—N1 | 1.134 (6) | C12—H12 | 0.9500 |
C1—C2 | 1.456 (6) | C13—H13 | 0.9500 |
C2—H2A | 0.9800 | C14—N4 | 1.445 (8) |
C2—H2B | 0.9800 | C14—C15 | 1.467 (10) |
C2—H2C | 0.9800 | C14—H14A | 0.9900 |
C3—N7 | 1.320 (6) | C14—H14B | 0.9900 |
C3—N5 | 1.332 (6) | C15—C16 | 1.3900 |
C3—H3 | 0.9500 | C15—C20 | 1.3900 |
C4—N6 | 1.313 (7) | C16—C17 | 1.3900 |
C4—N5 | 1.352 (6) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C17—C18 | 1.3900 |
C5—N3 | 1.326 (8) | C17—H17 | 0.9500 |
C5—N2 | 1.374 (7) | C18—C19 | 1.3900 |
C5—H5 | 0.9500 | C18—H18 | 0.9500 |
C6—N2 | 1.315 (7) | C19—C20 | 1.3900 |
C6—N4 | 1.342 (8) | C19—H19 | 0.9500 |
C6—H6 | 0.9500 | C20—H20 | 0.9500 |
C7—N7 | 1.467 (6) | C21—C22 | 1.457 (11) |
C7—C8 | 1.503 (7) | C21—H21A | 0.9800 |
C7—H7A | 0.9900 | C21—H21B | 0.9800 |
C7—H7B | 0.9900 | C21—H21C | 0.9800 |
C8—C13 | 1.363 (9) | C22—N8 | 1.126 (11) |
C8—C9B | 1.375 (16) | N1—Fe1 | 2.203 (4) |
C8—C9A | 1.414 (19) | N2—Fe1 | 2.175 (4) |
C9A—C10A | 1.40 (2) | N3—N4 | 1.331 (8) |
C9A—H9A | 0.9500 | N5—Fe1 | 2.150 (4) |
C10A—C11 | 1.41 (3) | N6—N7 | 1.360 (5) |
C10A—H10A | 0.9500 | O1—Fe2 | 1.7349 (7) |
C9B—C10B | 1.39 (2) | O1—Fe2i | 1.7349 (7) |
C9B—H9B | 0.9500 | Cl1—Fe2 | 2.2137 (17) |
C10B—C11 | 1.41 (3) | Cl2—Fe2 | 2.2334 (18) |
C10B—H10B | 0.9500 | Cl3—Fe2 | 2.2027 (18) |
C11—C12 | 1.367 (13) | Fe1—N5ii | 2.150 (4) |
C11—H11 | 0.9500 | Fe1—N2ii | 2.175 (4) |
C12—C13 | 1.381 (10) | Fe1—N1ii | 2.204 (4) |
N1—C1—C2 | 178.9 (6) | C20—C15—C14 | 123.2 (5) |
C1—C2—H2A | 109.5 | C15—C16—C17 | 120.0 |
C1—C2—H2B | 109.5 | C15—C16—H16 | 120.0 |
H2A—C2—H2B | 109.5 | C17—C16—H16 | 120.0 |
C1—C2—H2C | 109.5 | C18—C17—C16 | 120.0 |
H2A—C2—H2C | 109.5 | C18—C17—H17 | 120.0 |
H2B—C2—H2C | 109.5 | C16—C17—H17 | 120.0 |
N7—C3—N5 | 110.3 (4) | C17—C18—C19 | 120.0 |
N7—C3—H3 | 124.9 | C17—C18—H18 | 120.0 |
N5—C3—H3 | 124.9 | C19—C18—H18 | 120.0 |
N6—C4—N5 | 114.6 (4) | C20—C19—C18 | 120.0 |
N6—C4—H4 | 122.7 | C20—C19—H19 | 120.0 |
N5—C4—H4 | 122.7 | C18—C19—H19 | 120.0 |
N3—C5—N2 | 115.0 (6) | C19—C20—C15 | 120.0 |
N3—C5—H5 | 122.5 | C19—C20—H20 | 120.0 |
N2—C5—H5 | 122.5 | C15—C20—H20 | 120.0 |
N2—C6—N4 | 111.7 (6) | C22—C21—H21A | 109.5 |
N2—C6—H6 | 124.2 | C22—C21—H21B | 109.5 |
N4—C6—H6 | 124.2 | H21A—C21—H21B | 109.5 |
N7—C7—C8 | 111.7 (4) | C22—C21—H21C | 109.5 |
N7—C7—H7A | 109.3 | H21A—C21—H21C | 109.5 |
C8—C7—H7A | 109.3 | H21B—C21—H21C | 109.5 |
N7—C7—H7B | 109.3 | N8—C22—C21 | 176.3 (10) |
C8—C7—H7B | 109.3 | C1—N1—Fe1 | 178.7 (4) |
H7A—C7—H7B | 107.9 | C6—N2—C5 | 100.9 (5) |
C13—C8—C9B | 117.7 (8) | C6—N2—Fe1 | 132.2 (4) |
C13—C8—C9A | 115.1 (9) | C5—N2—Fe1 | 126.9 (3) |
C13—C8—C7 | 121.7 (5) | C5—N3—N4 | 102.6 (5) |
C9B—C8—C7 | 118.5 (10) | N3—N4—C6 | 109.8 (5) |
C9A—C8—C7 | 120.5 (10) | N3—N4—C14 | 121.4 (6) |
C10A—C9A—C8 | 122.8 (18) | C6—N4—C14 | 128.7 (6) |
C10A—C9A—H9A | 118.6 | C3—N5—C4 | 102.6 (4) |
C8—C9A—H9A | 118.6 | C3—N5—Fe1 | 128.1 (3) |
C9A—C10A—C11 | 115.2 (15) | C4—N5—Fe1 | 129.3 (3) |
C9A—C10A—H10A | 122.4 | C4—N6—N7 | 102.7 (4) |
C11—C10A—H10A | 122.4 | C3—N7—N6 | 109.8 (4) |
C8—C9B—C10B | 120.1 (16) | C3—N7—C7 | 129.3 (4) |
C8—C9B—H9B | 119.9 | N6—N7—C7 | 120.8 (4) |
C10B—C9B—H9B | 119.9 | Fe2—O1—Fe2i | 180.00 (6) |
C9B—C10B—C11 | 119.1 (15) | N5—Fe1—N5ii | 180.0 |
C9B—C10B—H10B | 120.5 | N5—Fe1—N2ii | 88.63 (14) |
C11—C10B—H10B | 120.5 | N5ii—Fe1—N2ii | 91.37 (14) |
C12—C11—C10B | 118.0 (9) | N5—Fe1—N2 | 91.37 (14) |
C12—C11—C10A | 119.7 (9) | N5ii—Fe1—N2 | 88.63 (14) |
C12—C11—H11 | 120.2 | N2ii—Fe1—N2 | 180.0 |
C10A—C11—H11 | 120.2 | N5—Fe1—N1 | 89.09 (14) |
C11—C12—C13 | 119.2 (8) | N5ii—Fe1—N1 | 90.91 (14) |
C11—C12—H12 | 120.4 | N2ii—Fe1—N1 | 90.90 (14) |
C13—C12—H12 | 120.4 | N2—Fe1—N1 | 89.10 (14) |
C8—C13—C12 | 121.8 (7) | N5—Fe1—N1ii | 90.91 (14) |
C8—C13—H13 | 119.1 | N5ii—Fe1—N1ii | 89.09 (14) |
C12—C13—H13 | 119.1 | N2ii—Fe1—N1ii | 89.10 (14) |
N4—C14—C15 | 110.8 (6) | N2—Fe1—N1ii | 90.90 (14) |
N4—C14—H14A | 109.5 | N1—Fe1—N1ii | 180.0 |
C15—C14—H14A | 109.5 | O1—Fe2—Cl3 | 108.34 (6) |
N4—C14—H14B | 109.5 | O1—Fe2—Cl1 | 109.30 (6) |
C15—C14—H14B | 109.5 | Cl3—Fe2—Cl1 | 111.70 (7) |
H14A—C14—H14B | 108.1 | O1—Fe2—Cl2 | 115.50 (7) |
C16—C15—C20 | 120.0 | Cl3—Fe2—Cl2 | 105.50 (8) |
C16—C15—C14 | 116.7 (5) | Cl1—Fe2—Cl2 | 106.52 (7) |
N7—C7—C8—C13 | −93.8 (7) | C17—C18—C19—C20 | 0.0 |
N7—C7—C8—C9B | 102.6 (16) | C18—C19—C20—C15 | 0.0 |
N7—C7—C8—C9A | 66.5 (15) | C16—C15—C20—C19 | 0.0 |
C13—C8—C9A—C10A | −19 (2) | C14—C15—C20—C19 | 175.8 (9) |
C9B—C8—C9A—C10A | 84 (3) | N4—C6—N2—C5 | 0.0 (6) |
C7—C8—C9A—C10A | 179.6 (13) | N4—C6—N2—Fe1 | 177.7 (4) |
C8—C9A—C10A—C11 | 0 (2) | N3—C5—N2—C6 | 0.4 (7) |
C13—C8—C9B—C10B | 15 (2) | N3—C5—N2—Fe1 | −177.4 (4) |
C9A—C8—C9B—C10B | −78 (3) | N2—C5—N3—N4 | −0.7 (7) |
C7—C8—C9B—C10B | 179.1 (14) | C5—N3—N4—C6 | 0.7 (7) |
C8—C9B—C10B—C11 | 1 (3) | C5—N3—N4—C14 | 178.1 (6) |
C9B—C10B—C11—C12 | −17 (3) | N2—C6—N4—N3 | −0.5 (7) |
C9B—C10B—C11—C10A | 85 (2) | N2—C6—N4—C14 | −177.6 (7) |
C9A—C10A—C11—C12 | 21 (2) | C15—C14—N4—N3 | 83.4 (9) |
C9A—C10A—C11—C10B | −75.7 (18) | C15—C14—N4—C6 | −99.8 (9) |
C10B—C11—C12—C13 | 15.9 (19) | N7—C3—N5—C4 | 0.4 (5) |
C10A—C11—C12—C13 | −21.6 (17) | N7—C3—N5—Fe1 | 178.4 (3) |
C9B—C8—C13—C12 | −16.3 (19) | N6—C4—N5—C3 | 0.0 (6) |
C9A—C8—C13—C12 | 18.6 (18) | N6—C4—N5—Fe1 | −178.0 (3) |
C7—C8—C13—C12 | 180.0 (6) | N5—C4—N6—N7 | −0.3 (6) |
C11—C12—C13—C8 | 0.8 (13) | N5—C3—N7—N6 | −0.6 (5) |
N4—C14—C15—C16 | −157.8 (6) | N5—C3—N7—C7 | −177.5 (4) |
N4—C14—C15—C20 | 26.3 (10) | C4—N6—N7—C3 | 0.5 (5) |
C20—C15—C16—C17 | 0.0 | C4—N6—N7—C7 | 177.7 (4) |
C14—C15—C16—C17 | −176.0 (8) | C8—C7—N7—C3 | −122.0 (5) |
C15—C16—C17—C18 | 0.0 | C8—C7—N7—N6 | 61.4 (6) |
C16—C17—C18—C19 | 0.0 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z. |