Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035240/ng2090sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035240/ng2090Isup2.hkl |
CCDC reference: 624930
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.005 Å
- R factor = 0.050
- wR factor = 0.108
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
[Fe(C23H22N4O2)] | Z = 2 |
Mr = 442.30 | F(000) = 460 |
Triclinic, P1 | Dx = 1.521 Mg m−3 |
a = 7.3830 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4020 (19) Å | Cell parameters from 25 reflections |
c = 13.3750 (15) Å | θ = 9–15° |
α = 112.310 (17)° | µ = 0.81 mm−1 |
β = 94.390 (18)° | T = 295 K |
γ = 108.06 (2)° | Block, red |
V = 965.9 (4) Å3 | 0.23 × 0.16 × 0.12 mm |
Enraf–Nonius CAD-4 diffractometer | 2813 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω/2θ scans | h = 0→9 |
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968) | k = −14→13 |
Tmin = 0.836, Tmax = 0.905 | l = −16→16 |
4090 measured reflections | 3 standard reflections every 200 reflections |
3776 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.035P)2 + 0.3269P] where P = (Fo2 + 2Fc2)/3 |
3776 reflections | (Δ/σ)max = 0.001 |
273 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Experimental. Spectroscopic analysis: IR (KBr, ν, cm-1): 1731 (versus, C═O); UV [λmax, nm, ε (× 104), in DMF]: 264.00 (3.37, K band), 358.00 (0.45, R band), 446.00 (0.069, d–d band); 1H NMR (600 MHz, CDCl3, δ, p.p.m.): 5.895 (s, 2H, 2CH), 4.509, 4.375 [s, 4H, s, 4H, (2H, 5H) and (3H, 4H) of two C5H4 rings], 3.147–3.145 (d, 4H, 2COCH2), 2.492 (d, 6H, 2CH3), 1.557–1.548 (d, 2H,CH2). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.76026 (7) | 0.70244 (5) | 0.71337 (4) | 0.02842 (15) | |
O1 | 0.6950 (5) | 1.3352 (3) | 0.8351 (2) | 0.0647 (9) | |
O2 | 1.0659 (4) | 1.3776 (3) | 0.7078 (3) | 0.0669 (9) | |
N1 | 0.6479 (4) | 1.1327 (3) | 0.8414 (2) | 0.0360 (7) | |
N2 | 0.5949 (4) | 0.9936 (3) | 0.7811 (2) | 0.0365 (7) | |
N3 | 0.9285 (4) | 1.0278 (3) | 0.6385 (2) | 0.0377 (7) | |
N4 | 1.0127 (4) | 1.1676 (3) | 0.7002 (3) | 0.0385 (7) | |
C1 | 0.6197 (6) | 1.2135 (4) | 0.5948 (3) | 0.0474 (10) | |
H1A | 0.6462 | 1.3097 | 0.6371 | 0.057* | |
H1B | 0.5216 | 1.1812 | 0.5282 | 0.057* | |
C2 | 0.5374 (6) | 1.1373 (4) | 0.6633 (3) | 0.0470 (10) | |
H2A | 0.3986 | 1.1200 | 0.6548 | 0.056* | |
H2B | 0.5526 | 1.0498 | 0.6341 | 0.056* | |
C3 | 0.6329 (6) | 1.2121 (4) | 0.7846 (3) | 0.0441 (10) | |
C4 | 0.7996 (7) | 1.3189 (4) | 1.0385 (3) | 0.0564 (12) | |
H4A | 0.8495 | 1.3225 | 1.1084 | 0.085* | |
H4B | 0.6910 | 1.3487 | 1.0440 | 0.085* | |
H4C | 0.9004 | 1.3774 | 1.0190 | 0.085* | |
C5 | 0.7338 (5) | 1.1755 (3) | 0.9512 (3) | 0.0388 (9) | |
C6 | 0.7351 (5) | 1.0619 (3) | 0.9599 (3) | 0.0396 (9) | |
H6 | 0.7827 | 1.0565 | 1.0238 | 0.047* | |
C7 | 0.6504 (5) | 0.9524 (3) | 0.8538 (3) | 0.0320 (8) | |
C8 | 0.6232 (5) | 0.8086 (3) | 0.8206 (3) | 0.0313 (8) | |
C9 | 0.7320 (5) | 0.7574 (3) | 0.8743 (3) | 0.0362 (8) | |
H9 | 0.8329 | 0.8093 | 0.9372 | 0.043* | |
C10 | 0.6598 (6) | 0.6135 (3) | 0.8152 (3) | 0.0423 (9) | |
H10 | 0.7054 | 0.5546 | 0.8325 | 0.051* | |
C11 | 0.5083 (6) | 0.5755 (4) | 0.7266 (3) | 0.0435 (10) | |
H11 | 0.4352 | 0.4867 | 0.6752 | 0.052* | |
C12 | 0.4846 (5) | 0.6951 (3) | 0.7280 (3) | 0.0391 (9) | |
H12 | 0.3947 | 0.6986 | 0.6775 | 0.047* | |
C13 | 1.0492 (5) | 0.7686 (3) | 0.7081 (3) | 0.0350 (8) | |
H13 | 1.1545 | 0.8146 | 0.7688 | 0.042* | |
C14 | 0.9608 (5) | 0.6245 (3) | 0.6465 (3) | 0.0379 (9) | |
H14 | 0.9981 | 0.5599 | 0.6596 | 0.046* | |
C15 | 0.8069 (6) | 0.5976 (4) | 0.5621 (3) | 0.0418 (9) | |
H15 | 0.7250 | 0.5117 | 0.5093 | 0.050* | |
C16 | 0.7983 (5) | 0.7233 (3) | 0.5713 (3) | 0.0369 (9) | |
H16 | 0.7089 | 0.7342 | 0.5259 | 0.044* | |
C17 | 0.9489 (5) | 0.8300 (3) | 0.6611 (3) | 0.0328 (8) | |
C18 | 1.0000 (5) | 0.9775 (3) | 0.6988 (3) | 0.0332 (8) | |
C19 | 1.1293 (5) | 1.0820 (3) | 0.7985 (3) | 0.0366 (9) | |
H19 | 1.1964 | 1.0704 | 0.8537 | 0.044* | |
C20 | 1.1367 (5) | 1.2024 (3) | 0.7982 (3) | 0.0360 (8) | |
C21 | 1.2475 (6) | 1.3443 (4) | 0.8837 (3) | 0.0549 (11) | |
H21A | 1.3187 | 1.3415 | 0.9454 | 0.082* | |
H21B | 1.1580 | 1.3890 | 0.9084 | 0.082* | |
H21C | 1.3372 | 1.3935 | 0.8522 | 0.082* | |
C22 | 0.9727 (6) | 1.2575 (4) | 0.6595 (4) | 0.0470 (10) | |
C23 | 0.8066 (6) | 1.1965 (4) | 0.5617 (3) | 0.0473 (10) | |
H23A | 0.7821 | 1.1001 | 0.5218 | 0.057* | |
H23B | 0.8428 | 1.2394 | 0.5122 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0294 (3) | 0.0217 (2) | 0.0338 (3) | 0.0108 (2) | 0.0063 (2) | 0.0105 (2) |
O1 | 0.107 (3) | 0.0331 (16) | 0.0591 (19) | 0.0310 (17) | 0.0183 (18) | 0.0203 (14) |
O2 | 0.058 (2) | 0.0400 (17) | 0.107 (3) | 0.0125 (15) | 0.0035 (18) | 0.0431 (18) |
N1 | 0.0420 (18) | 0.0267 (15) | 0.0424 (18) | 0.0182 (14) | 0.0116 (15) | 0.0129 (14) |
N2 | 0.0399 (18) | 0.0257 (15) | 0.0419 (18) | 0.0163 (14) | 0.0109 (14) | 0.0087 (13) |
N3 | 0.0410 (18) | 0.0304 (16) | 0.0465 (19) | 0.0147 (14) | 0.0132 (15) | 0.0193 (14) |
N4 | 0.0417 (18) | 0.0317 (16) | 0.050 (2) | 0.0165 (14) | 0.0140 (15) | 0.0227 (15) |
C1 | 0.052 (3) | 0.052 (2) | 0.053 (3) | 0.031 (2) | 0.009 (2) | 0.029 (2) |
C2 | 0.042 (2) | 0.051 (2) | 0.055 (3) | 0.021 (2) | 0.013 (2) | 0.027 (2) |
C3 | 0.046 (2) | 0.044 (2) | 0.052 (3) | 0.022 (2) | 0.019 (2) | 0.024 (2) |
C4 | 0.086 (3) | 0.034 (2) | 0.047 (3) | 0.026 (2) | 0.017 (2) | 0.0112 (19) |
C5 | 0.047 (2) | 0.0298 (19) | 0.039 (2) | 0.0162 (17) | 0.0165 (18) | 0.0112 (16) |
C6 | 0.051 (2) | 0.0313 (19) | 0.034 (2) | 0.0134 (18) | 0.0102 (18) | 0.0131 (16) |
C7 | 0.0317 (19) | 0.0297 (18) | 0.040 (2) | 0.0162 (16) | 0.0148 (16) | 0.0145 (16) |
C8 | 0.0319 (19) | 0.0269 (18) | 0.036 (2) | 0.0113 (15) | 0.0125 (16) | 0.0127 (15) |
C9 | 0.042 (2) | 0.0288 (18) | 0.035 (2) | 0.0125 (17) | 0.0081 (17) | 0.0109 (16) |
C10 | 0.054 (3) | 0.0287 (19) | 0.051 (2) | 0.0165 (18) | 0.019 (2) | 0.0211 (18) |
C11 | 0.040 (2) | 0.0232 (18) | 0.059 (3) | 0.0072 (17) | 0.016 (2) | 0.0120 (18) |
C12 | 0.0275 (19) | 0.035 (2) | 0.051 (2) | 0.0129 (16) | 0.0110 (17) | 0.0138 (18) |
C13 | 0.032 (2) | 0.0320 (19) | 0.042 (2) | 0.0163 (16) | 0.0098 (17) | 0.0132 (17) |
C14 | 0.040 (2) | 0.0303 (19) | 0.049 (2) | 0.0241 (17) | 0.0150 (18) | 0.0133 (17) |
C15 | 0.050 (2) | 0.0301 (19) | 0.036 (2) | 0.0168 (18) | 0.0088 (18) | 0.0034 (16) |
C16 | 0.046 (2) | 0.035 (2) | 0.031 (2) | 0.0195 (18) | 0.0063 (17) | 0.0125 (16) |
C17 | 0.036 (2) | 0.0324 (19) | 0.040 (2) | 0.0174 (16) | 0.0170 (17) | 0.0198 (16) |
C18 | 0.034 (2) | 0.0365 (19) | 0.039 (2) | 0.0171 (16) | 0.0183 (16) | 0.0209 (17) |
C19 | 0.041 (2) | 0.0353 (19) | 0.041 (2) | 0.0152 (17) | 0.0138 (18) | 0.0225 (17) |
C20 | 0.038 (2) | 0.0320 (19) | 0.045 (2) | 0.0154 (17) | 0.0211 (18) | 0.0192 (17) |
C21 | 0.071 (3) | 0.033 (2) | 0.055 (3) | 0.014 (2) | 0.018 (2) | 0.0158 (19) |
C22 | 0.044 (2) | 0.048 (2) | 0.072 (3) | 0.024 (2) | 0.023 (2) | 0.041 (2) |
C23 | 0.054 (3) | 0.052 (2) | 0.052 (3) | 0.025 (2) | 0.017 (2) | 0.034 (2) |
Fe1—C8 | 2.052 (3) | N3—C18 | 1.317 (4) |
Fe1—C9 | 2.048 (4) | N4—C20 | 1.382 (5) |
Fe1—C10 | 2.043 (4) | N4—C22 | 1.420 (4) |
Fe1—C11 | 2.040 (4) | C8—C12 | 1.422 (5) |
Fe1—C12 | 2.039 (4) | C8—C9 | 1.423 (5) |
Fe1—C13 | 2.047 (4) | C9—C10 | 1.417 (5) |
Fe1—C14 | 2.049 (3) | C9—H9 | 0.9300 |
Fe1—C15 | 2.042 (4) | C10—C11 | 1.396 (5) |
Fe1—C17 | 2.051 (3) | C10—H10 | 0.9300 |
Fe1—C16 | 2.033 (4) | C11—C12 | 1.422 (5) |
C1—C2 | 1.525 (5) | C11—H11 | 0.9300 |
C1—C23 | 1.527 (5) | C12—H12 | 0.9300 |
C1—H1A | 0.9700 | C14—C15 | 1.408 (5) |
C1—H1B | 0.9700 | C14—C13 | 1.425 (5) |
C2—H2A | 0.9700 | C14—H14 | 0.9300 |
C2—H2B | 0.9700 | C15—C16 | 1.413 (5) |
C2—C3 | 1.503 (5) | C15—H15 | 0.9300 |
O1—C3 | 1.212 (4) | C16—C17 | 1.417 (5) |
N1—N2 | 1.384 (4) | C16—H16 | 0.9300 |
N1—C3 | 1.408 (5) | C17—C13 | 1.420 (5) |
N1—C5 | 1.384 (4) | C17—C18 | 1.470 (4) |
N2—C7 | 1.319 (4) | C13—H13 | 0.9300 |
C4—C5 | 1.498 (5) | C18—C19 | 1.415 (5) |
C4—H4A | 0.9600 | C19—C20 | 1.360 (5) |
C4—H4B | 0.9600 | C19—H19 | 0.9300 |
C4—H4C | 0.9600 | C20—C21 | 1.491 (5) |
C5—C6 | 1.348 (5) | C21—H21A | 0.9600 |
C6—C7 | 1.414 (5) | C21—H21B | 0.9600 |
C6—H6 | 0.9300 | C21—H21C | 0.9600 |
C7—C8 | 1.467 (4) | C22—C23 | 1.494 (5) |
O2—C22 | 1.201 (5) | C23—H23A | 0.9700 |
N3—N4 | 1.384 (4) | C23—H23B | 0.9700 |
C16—Fe1—C12 | 106.62 (16) | C12—C8—C7 | 126.2 (3) |
C16—Fe1—C11 | 123.28 (16) | C9—C8—C7 | 126.3 (3) |
C12—Fe1—C11 | 40.81 (14) | C12—C8—Fe1 | 69.2 (2) |
C16—Fe1—C15 | 40.60 (14) | C9—C8—Fe1 | 69.56 (19) |
C12—Fe1—C15 | 119.33 (16) | C7—C8—Fe1 | 126.1 (2) |
C11—Fe1—C15 | 105.71 (16) | C10—C9—C8 | 108.0 (3) |
C16—Fe1—C10 | 159.47 (14) | C10—C9—Fe1 | 69.5 (2) |
C12—Fe1—C10 | 68.24 (16) | C8—C9—Fe1 | 69.8 (2) |
C11—Fe1—C10 | 40.00 (15) | C10—C9—H9 | 126.0 |
C15—Fe1—C10 | 123.12 (15) | C8—C9—H9 | 126.0 |
C16—Fe1—C13 | 68.10 (15) | Fe1—C9—H9 | 126.3 |
C12—Fe1—C13 | 162.90 (13) | C11—C10—C9 | 108.2 (3) |
C11—Fe1—C13 | 155.76 (14) | C11—C10—Fe1 | 69.9 (2) |
C15—Fe1—C13 | 68.01 (15) | C9—C10—Fe1 | 69.9 (2) |
C10—Fe1—C13 | 122.43 (16) | C11—C10—H10 | 125.9 |
C16—Fe1—C9 | 157.96 (13) | C9—C10—H10 | 125.9 |
C12—Fe1—C9 | 68.31 (15) | Fe1—C10—H10 | 125.9 |
C11—Fe1—C9 | 67.79 (15) | C10—C11—C12 | 108.6 (3) |
C15—Fe1—C9 | 160.91 (14) | C10—C11—Fe1 | 70.1 (2) |
C10—Fe1—C9 | 40.54 (13) | C12—C11—Fe1 | 69.5 (2) |
C13—Fe1—C9 | 110.10 (15) | C10—C11—H11 | 125.7 |
C16—Fe1—C14 | 68.17 (15) | C12—C11—H11 | 125.7 |
C12—Fe1—C14 | 154.23 (14) | Fe1—C11—H11 | 126.3 |
C11—Fe1—C14 | 119.43 (14) | C11—C12—C8 | 107.6 (3) |
C15—Fe1—C14 | 40.28 (14) | C11—C12—Fe1 | 69.7 (2) |
C10—Fe1—C14 | 107.32 (15) | C8—C12—Fe1 | 70.2 (2) |
C13—Fe1—C14 | 40.71 (13) | C11—C12—H12 | 126.2 |
C9—Fe1—C14 | 125.82 (15) | C8—C12—H12 | 126.2 |
C16—Fe1—C17 | 40.59 (14) | Fe1—C12—H12 | 125.6 |
C12—Fe1—C17 | 125.01 (14) | C15—C14—C13 | 107.6 (3) |
C11—Fe1—C17 | 160.97 (15) | C15—C14—Fe1 | 69.6 (2) |
C15—Fe1—C17 | 68.27 (14) | C13—C14—Fe1 | 69.6 (2) |
C10—Fe1—C17 | 158.33 (15) | C15—C14—H14 | 126.2 |
C13—Fe1—C17 | 40.56 (13) | C13—C14—H14 | 126.2 |
C9—Fe1—C17 | 123.56 (14) | Fe1—C14—H14 | 126.2 |
C14—Fe1—C17 | 68.44 (14) | C14—C15—C16 | 108.3 (3) |
C16—Fe1—C8 | 121.63 (14) | C14—C15—Fe1 | 70.1 (2) |
C12—Fe1—C8 | 40.69 (14) | C16—C15—Fe1 | 69.4 (2) |
C11—Fe1—C8 | 68.24 (14) | C14—C15—H15 | 125.8 |
C15—Fe1—C8 | 155.64 (15) | C16—C15—H15 | 125.8 |
C10—Fe1—C8 | 68.29 (14) | Fe1—C15—H15 | 126.2 |
C13—Fe1—C8 | 127.01 (14) | C15—C16—C17 | 108.5 (3) |
C9—Fe1—C8 | 40.61 (13) | C15—C16—Fe1 | 70.0 (2) |
C14—Fe1—C8 | 163.41 (14) | C17—C16—Fe1 | 70.4 (2) |
C17—Fe1—C8 | 109.36 (13) | C15—C16—H16 | 125.8 |
N2—N1—C5 | 112.0 (3) | C17—C16—H16 | 125.8 |
N2—N1—C3 | 118.7 (3) | Fe1—C16—H16 | 125.4 |
C5—N1—C3 | 128.7 (3) | C16—C17—C13 | 107.3 (3) |
C7—N2—N1 | 104.0 (3) | C16—C17—C18 | 127.7 (3) |
C18—N3—N4 | 104.3 (3) | C13—C17—C18 | 125.1 (3) |
C20—N4—N3 | 112.0 (3) | C16—C17—Fe1 | 69.0 (2) |
C20—N4—C22 | 127.3 (3) | C13—C17—Fe1 | 69.57 (19) |
N3—N4—C22 | 120.6 (3) | C18—C17—Fe1 | 128.0 (2) |
C2—C1—C23 | 113.7 (3) | C17—C13—C14 | 108.3 (3) |
C2—C1—H1A | 108.8 | C17—C13—Fe1 | 69.9 (2) |
C23—C1—H1A | 108.8 | C14—C13—Fe1 | 69.7 (2) |
C2—C1—H1B | 108.8 | C17—C13—H13 | 125.9 |
C23—C1—H1B | 108.8 | C14—C13—H13 | 125.9 |
H1A—C1—H1B | 107.7 | Fe1—C13—H13 | 126.1 |
C3—C2—C1 | 114.0 (3) | N3—C18—C19 | 111.5 (3) |
C3—C2—H2A | 108.8 | N3—C18—C17 | 121.7 (3) |
C1—C2—H2A | 108.8 | C19—C18—C17 | 126.8 (3) |
C3—C2—H2B | 108.8 | C20—C19—C18 | 106.8 (3) |
C1—C2—H2B | 108.8 | C20—C19—H19 | 126.6 |
H2A—C2—H2B | 107.6 | C18—C19—H19 | 126.6 |
O1—C3—N1 | 119.1 (4) | C19—C20—N4 | 105.3 (3) |
O1—C3—C2 | 123.7 (4) | C19—C20—C21 | 129.4 (4) |
N1—C3—C2 | 117.1 (3) | N4—C20—C21 | 125.3 (3) |
C5—C4—H4A | 109.5 | C20—C21—H21A | 109.5 |
C5—C4—H4B | 109.5 | C20—C21—H21B | 109.5 |
H4A—C4—H4B | 109.5 | H21A—C21—H21B | 109.5 |
C5—C4—H4C | 109.5 | C20—C21—H21C | 109.5 |
H4A—C4—H4C | 109.5 | H21A—C21—H21C | 109.5 |
H4B—C4—H4C | 109.5 | H21B—C21—H21C | 109.5 |
C6—C5—N1 | 105.3 (3) | O2—C22—N4 | 119.1 (4) |
C6—C5—C4 | 129.7 (4) | O2—C22—C23 | 123.6 (4) |
N1—C5—C4 | 124.9 (3) | N4—C22—C23 | 117.2 (3) |
C5—C6—C7 | 107.2 (3) | C22—C23—C1 | 112.4 (3) |
C5—C6—H6 | 126.4 | C22—C23—H23A | 109.1 |
C7—C6—H6 | 126.4 | C1—C23—H23A | 109.1 |
N2—C7—C6 | 111.5 (3) | C22—C23—H23B | 109.1 |
N2—C7—C8 | 120.7 (3) | C1—C23—H23B | 109.1 |
C6—C7—C8 | 127.8 (3) | H23A—C23—H23B | 107.8 |
C12—C8—C9 | 107.5 (3) | ||
C5—N1—N2—C7 | −0.7 (4) | C17—Fe1—C12—C8 | −78.8 (3) |
C3—N1—N2—C7 | 171.6 (3) | C16—Fe1—C14—C15 | −37.6 (2) |
C18—N3—N4—C20 | 0.3 (4) | C12—Fe1—C14—C15 | 45.5 (4) |
C18—N3—N4—C22 | 178.6 (3) | C11—Fe1—C14—C15 | 79.3 (3) |
C23—C1—C2—C3 | 82.3 (4) | C10—Fe1—C14—C15 | 121.1 (2) |
N2—N1—C3—O1 | −173.5 (3) | C13—Fe1—C14—C15 | −118.9 (3) |
C5—N1—C3—O1 | −2.8 (6) | C9—Fe1—C14—C15 | 162.0 (2) |
N2—N1—C3—C2 | 7.0 (5) | C17—Fe1—C14—C15 | −81.4 (2) |
C5—N1—C3—C2 | 177.8 (3) | C8—Fe1—C14—C15 | −166.9 (4) |
C1—C2—C3—O1 | 33.2 (6) | C16—Fe1—C14—C13 | 81.3 (2) |
C1—C2—C3—N1 | −147.3 (3) | C12—Fe1—C14—C13 | 164.4 (3) |
N2—N1—C5—C6 | 0.1 (4) | C11—Fe1—C14—C13 | −161.7 (2) |
C3—N1—C5—C6 | −171.1 (4) | C15—Fe1—C14—C13 | 118.9 (3) |
N2—N1—C5—C4 | −177.4 (4) | C10—Fe1—C14—C13 | −119.9 (2) |
C3—N1—C5—C4 | 11.3 (6) | C9—Fe1—C14—C13 | −79.1 (3) |
N1—C5—C6—C7 | 0.5 (4) | C17—Fe1—C14—C13 | 37.5 (2) |
C4—C5—C6—C7 | 177.8 (4) | C8—Fe1—C14—C13 | −48.0 (6) |
N1—N2—C7—C6 | 0.9 (4) | C13—C14—C15—C16 | −0.3 (4) |
N1—N2—C7—C8 | −178.5 (3) | Fe1—C14—C15—C16 | 59.0 (3) |
C5—C6—C7—N2 | −0.9 (4) | C13—C14—C15—Fe1 | −59.4 (3) |
C5—C6—C7—C8 | 178.5 (3) | C16—Fe1—C15—C14 | 119.5 (3) |
N2—C7—C8—C12 | −23.3 (5) | C12—Fe1—C15—C14 | −159.2 (2) |
C6—C7—C8—C12 | 157.4 (4) | C11—Fe1—C15—C14 | −117.2 (2) |
N2—C7—C8—C9 | 156.0 (3) | C10—Fe1—C15—C14 | −77.3 (3) |
C6—C7—C8—C9 | −23.4 (6) | C13—Fe1—C15—C14 | 38.0 (2) |
N2—C7—C8—Fe1 | 66.0 (4) | C9—Fe1—C15—C14 | −50.1 (5) |
C6—C7—C8—Fe1 | −113.3 (4) | C17—Fe1—C15—C14 | 81.9 (2) |
C16—Fe1—C8—C12 | 78.4 (2) | C8—Fe1—C15—C14 | 171.0 (3) |
C11—Fe1—C8—C12 | −38.2 (2) | C12—Fe1—C15—C16 | 81.3 (3) |
C15—Fe1—C8—C12 | 41.7 (4) | C11—Fe1—C15—C16 | 123.2 (2) |
C10—Fe1—C8—C12 | −81.4 (2) | C10—Fe1—C15—C16 | 163.2 (2) |
C13—Fe1—C8—C12 | 163.6 (2) | C13—Fe1—C15—C16 | −81.6 (2) |
C9—Fe1—C8—C12 | −119.0 (3) | C9—Fe1—C15—C16 | −169.6 (4) |
C14—Fe1—C8—C12 | −159.1 (4) | C14—Fe1—C15—C16 | −119.5 (3) |
C17—Fe1—C8—C12 | 121.6 (2) | C17—Fe1—C15—C16 | −37.7 (2) |
C16—Fe1—C8—C9 | −162.6 (2) | C8—Fe1—C15—C16 | 51.4 (4) |
C12—Fe1—C8—C9 | 119.0 (3) | C14—C15—C16—C17 | 0.6 (4) |
C11—Fe1—C8—C9 | 80.8 (2) | Fe1—C15—C16—C17 | 60.1 (3) |
C15—Fe1—C8—C9 | 160.7 (3) | C14—C15—C16—Fe1 | −59.5 (3) |
C10—Fe1—C8—C9 | 37.6 (2) | C12—Fe1—C16—C15 | −115.9 (2) |
C13—Fe1—C8—C9 | −77.4 (2) | C11—Fe1—C16—C15 | −74.4 (3) |
C14—Fe1—C8—C9 | −40.0 (6) | C10—Fe1—C16—C15 | −43.8 (5) |
C17—Fe1—C8—C9 | −119.4 (2) | C13—Fe1—C16—C15 | 81.3 (2) |
C16—Fe1—C8—C7 | −41.9 (4) | C9—Fe1—C16—C15 | 171.0 (4) |
C12—Fe1—C8—C7 | −120.3 (4) | C14—Fe1—C16—C15 | 37.3 (2) |
C11—Fe1—C8—C7 | −158.6 (4) | C17—Fe1—C16—C15 | 119.2 (3) |
C15—Fe1—C8—C7 | −78.6 (5) | C8—Fe1—C16—C15 | −157.7 (2) |
C10—Fe1—C8—C7 | 158.2 (4) | C12—Fe1—C16—C17 | 124.9 (2) |
C13—Fe1—C8—C7 | 43.2 (4) | C11—Fe1—C16—C17 | 166.4 (2) |
C9—Fe1—C8—C7 | 120.6 (4) | C15—Fe1—C16—C17 | −119.2 (3) |
C14—Fe1—C8—C7 | 80.6 (6) | C10—Fe1—C16—C17 | −163.0 (4) |
C17—Fe1—C8—C7 | 1.3 (3) | C13—Fe1—C16—C17 | −37.9 (2) |
C12—C8—C9—C10 | −0.3 (4) | C9—Fe1—C16—C17 | 51.8 (5) |
C7—C8—C9—C10 | −179.6 (3) | C14—Fe1—C16—C17 | −81.9 (2) |
Fe1—C8—C9—C10 | −59.2 (3) | C8—Fe1—C16—C17 | 83.1 (2) |
C12—C8—C9—Fe1 | 59.0 (2) | C15—C16—C17—C13 | −0.6 (4) |
C7—C8—C9—Fe1 | −120.4 (3) | Fe1—C16—C17—C13 | 59.3 (2) |
C16—Fe1—C9—C10 | 162.1 (4) | C15—C16—C17—C18 | 177.6 (3) |
C12—Fe1—C9—C10 | 81.4 (2) | Fe1—C16—C17—C18 | −122.5 (4) |
C11—Fe1—C9—C10 | 37.3 (2) | C15—C16—C17—Fe1 | −59.9 (3) |
C15—Fe1—C9—C10 | −36.1 (6) | C12—Fe1—C17—C16 | −73.7 (2) |
C13—Fe1—C9—C10 | −116.8 (2) | C11—Fe1—C17—C16 | −37.1 (5) |
C14—Fe1—C9—C10 | −73.8 (3) | C15—Fe1—C17—C16 | 37.7 (2) |
C17—Fe1—C9—C10 | −160.1 (2) | C10—Fe1—C17—C16 | 163.8 (4) |
C8—Fe1—C9—C10 | 119.3 (3) | C13—Fe1—C17—C16 | 118.8 (3) |
C16—Fe1—C9—C8 | 42.8 (5) | C9—Fe1—C17—C16 | −159.3 (2) |
C12—Fe1—C9—C8 | −37.8 (2) | C14—Fe1—C17—C16 | 81.2 (2) |
C11—Fe1—C9—C8 | −82.0 (2) | C8—Fe1—C17—C16 | −116.4 (2) |
C15—Fe1—C9—C8 | −155.4 (4) | C16—Fe1—C17—C13 | −118.8 (3) |
C10—Fe1—C9—C8 | −119.3 (3) | C12—Fe1—C17—C13 | 167.5 (2) |
C13—Fe1—C9—C8 | 123.9 (2) | C11—Fe1—C17—C13 | −156.0 (4) |
C14—Fe1—C9—C8 | 166.91 (19) | C15—Fe1—C17—C13 | −81.1 (2) |
C17—Fe1—C9—C8 | 80.6 (2) | C10—Fe1—C17—C13 | 45.0 (5) |
C8—C9—C10—C11 | −0.2 (4) | C9—Fe1—C17—C13 | 81.9 (2) |
Fe1—C9—C10—C11 | −59.6 (3) | C14—Fe1—C17—C13 | −37.6 (2) |
C8—C9—C10—Fe1 | 59.4 (2) | C8—Fe1—C17—C13 | 124.8 (2) |
C16—Fe1—C10—C11 | −41.6 (5) | C16—Fe1—C17—C18 | 122.0 (4) |
C12—Fe1—C10—C11 | 37.6 (2) | C12—Fe1—C17—C18 | 48.4 (4) |
C15—Fe1—C10—C11 | −74.1 (3) | C11—Fe1—C17—C18 | 84.9 (5) |
C13—Fe1—C10—C11 | −157.4 (2) | C15—Fe1—C17—C18 | 159.7 (4) |
C9—Fe1—C10—C11 | 119.2 (3) | C10—Fe1—C17—C18 | −74.1 (5) |
C14—Fe1—C10—C11 | −115.4 (2) | C13—Fe1—C17—C18 | −119.1 (4) |
C17—Fe1—C10—C11 | 169.5 (3) | C9—Fe1—C17—C18 | −37.2 (4) |
C8—Fe1—C10—C11 | 81.6 (2) | C14—Fe1—C17—C18 | −156.8 (4) |
C16—Fe1—C10—C9 | −160.8 (4) | C8—Fe1—C17—C18 | 5.7 (4) |
C12—Fe1—C10—C9 | −81.6 (2) | C16—C17—C13—C14 | 0.4 (4) |
C11—Fe1—C10—C9 | −119.2 (3) | C18—C17—C13—C14 | −177.8 (3) |
C15—Fe1—C10—C9 | 166.7 (2) | Fe1—C17—C13—C14 | 59.4 (2) |
C13—Fe1—C10—C9 | 83.3 (3) | C16—C17—C13—Fe1 | −58.9 (2) |
C14—Fe1—C10—C9 | 125.4 (2) | C18—C17—C13—Fe1 | 122.8 (3) |
C17—Fe1—C10—C9 | 50.3 (5) | C15—C14—C13—C17 | −0.1 (4) |
C8—Fe1—C10—C9 | −37.7 (2) | Fe1—C14—C13—C17 | −59.4 (2) |
C9—C10—C11—C12 | 0.6 (4) | C15—C14—C13—Fe1 | 59.4 (3) |
Fe1—C10—C11—C12 | −59.0 (3) | C16—Fe1—C13—C17 | 37.9 (2) |
C9—C10—C11—Fe1 | 59.7 (3) | C12—Fe1—C13—C17 | −37.1 (6) |
C16—Fe1—C11—C10 | 163.8 (2) | C11—Fe1—C13—C17 | 161.1 (3) |
C12—Fe1—C11—C10 | −119.8 (3) | C15—Fe1—C13—C17 | 81.8 (2) |
C15—Fe1—C11—C10 | 123.2 (2) | C10—Fe1—C13—C17 | −162.0 (2) |
C13—Fe1—C11—C10 | 52.0 (5) | C9—Fe1—C13—C17 | −118.5 (2) |
C9—Fe1—C11—C10 | −37.8 (2) | C14—Fe1—C13—C17 | 119.4 (3) |
C14—Fe1—C11—C10 | 81.9 (3) | C8—Fe1—C13—C17 | −76.0 (2) |
C17—Fe1—C11—C10 | −168.1 (4) | C16—Fe1—C13—C14 | −81.5 (2) |
C8—Fe1—C11—C10 | −81.7 (2) | C12—Fe1—C13—C14 | −156.6 (5) |
C16—Fe1—C11—C12 | −76.3 (3) | C11—Fe1—C13—C14 | 41.7 (5) |
C15—Fe1—C11—C12 | −116.9 (2) | C15—Fe1—C13—C14 | −37.6 (2) |
C10—Fe1—C11—C12 | 119.8 (3) | C10—Fe1—C13—C14 | 78.6 (3) |
C13—Fe1—C11—C12 | 171.9 (3) | C9—Fe1—C13—C14 | 122.0 (2) |
C9—Fe1—C11—C12 | 82.1 (2) | C17—Fe1—C13—C14 | −119.4 (3) |
C14—Fe1—C11—C12 | −158.2 (2) | C8—Fe1—C13—C14 | 164.6 (2) |
C17—Fe1—C11—C12 | −48.3 (5) | N4—N3—C18—C19 | −0.1 (4) |
C8—Fe1—C11—C12 | 38.1 (2) | N4—N3—C18—C17 | −178.8 (3) |
C10—C11—C12—C8 | −0.8 (4) | C16—C17—C18—N3 | −12.3 (6) |
Fe1—C11—C12—C8 | −60.2 (2) | C13—C17—C18—N3 | 165.7 (3) |
C10—C11—C12—Fe1 | 59.4 (3) | Fe1—C17—C18—N3 | −103.9 (4) |
C9—C8—C12—C11 | 0.6 (4) | C16—C17—C18—C19 | 169.2 (4) |
C7—C8—C12—C11 | −180.0 (3) | C13—C17—C18—C19 | −12.9 (6) |
Fe1—C8—C12—C11 | 59.9 (2) | Fe1—C17—C18—C19 | 77.5 (5) |
C9—C8—C12—Fe1 | −59.2 (2) | N3—C18—C19—C20 | −0.2 (4) |
C7—C8—C12—Fe1 | 120.2 (3) | C17—C18—C19—C20 | 178.5 (3) |
C16—Fe1—C12—C11 | 122.0 (2) | C18—C19—C20—N4 | 0.3 (4) |
C15—Fe1—C12—C11 | 79.9 (3) | C18—C19—C20—C21 | 178.9 (4) |
C10—Fe1—C12—C11 | −36.9 (2) | N3—N4—C20—C19 | −0.4 (4) |
C13—Fe1—C12—C11 | −168.7 (5) | C22—N4—C20—C19 | −178.5 (3) |
C9—Fe1—C12—C11 | −80.7 (2) | N3—N4—C20—C21 | −179.1 (3) |
C14—Fe1—C12—C11 | 48.0 (4) | C22—N4—C20—C21 | 2.8 (6) |
C17—Fe1—C12—C11 | 162.7 (2) | C20—N4—C22—O2 | 7.3 (6) |
C8—Fe1—C12—C11 | −118.5 (3) | N3—N4—C22—O2 | −170.7 (4) |
C16—Fe1—C12—C8 | −119.5 (2) | C20—N4—C22—C23 | −169.2 (3) |
C11—Fe1—C12—C8 | 118.5 (3) | N3—N4—C22—C23 | 12.9 (5) |
C15—Fe1—C12—C8 | −161.7 (2) | O2—C22—C23—C1 | −77.7 (5) |
C10—Fe1—C12—C8 | 81.6 (2) | N4—C22—C23—C1 | 98.5 (4) |
C13—Fe1—C12—C8 | −50.2 (6) | C2—C1—C23—C22 | −64.7 (5) |
C9—Fe1—C12—C8 | 37.8 (2) | C2—C1—C23—C22 | −64.7 (5) |
C14—Fe1—C12—C8 | 166.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1i | 0.93 | 2.49 | 3.369 (5) | 157 |
C14—H14···O2i | 0.93 | 2.57 | 3.494 (5) | 173 |
C2—H2A···Cg2ii | 0.97 | 2.84 | 3.746 (5) | 155 |
C23—H23B···Cg4iii | 0.97 | 2.82 | 3.680 (5) | 149 |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) −x+2, −y+2, −z+1. |