metal-organic compounds
(6-Chloropyridazin-3-yl)ferrocene
aSchool of Chemical Engineering and Energy, Zhengzhou University, Henan, Zhengzhou, 450052, People's Republic of China, bSchool of Food and Bioengineering, Zhengzhou University of Light Industry, Henan, Zhengzhou, 450052, People's Republic of China, and cHenan Industrial University Chemical Technology Vocational College, Henan, Zhengzhou, 450052, People's Republic of China
*Correspondence e-mail: zhaowenen@zzu.edu.cn
The 5H5)(C9H6ClN2)], contains two independent molecules in which the cyclopentadienyl rings are almost parallel, making dihedral angles of 2.16 (4) and 2.71 (5), and the dihedral angles between the pyridazinyl and substituted cyclopentadienyl rings are 9.65 (5) and 11.53 (8)°. In the crystal, molecules are linked by C—H⋯N hydrogen bonds into chains along the c-axis direction.
of the title compound, [Fe(CCCDC reference: 972112
Related literature
For the synthesis of the title compound, see: Xu et al. (2012). For applications of organomercury compounds, see: Beletskaya et al. (2001); Tsvetkov et al. (2000); Xu et al. (2010); For palladium-catalysed reactions, see: Meijere & Diederich (2004).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 972112
https://doi.org/10.1107/S1600536813031310/rn2116sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813031310/rn2116Isup2.hkl
The title compound was obtained from the coupling reaction of chloromercuriferrocene and 3,6-dichloropyridazine as described in literature (Xu et al., 2012) and recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.
H atoms attached to C atoms of the title compound were placed in geometrically idealized positions and treated as riding with C—H distances constrained to 0.93–0.96 Å.
Palladium catalyzed coupling reactions are widely used and powerful tools in organic synthesis (Meijere & Diederich, 2004). The organomercury compounds have a number of notable advantages over other organometallic compounds commonly used in cross-coupling reactions, including higher selectivity of reactions, extra stability, as well as easy availability by a direct mercuration of ferrocene (Beletskaya et al., 2001; Tsvetkov et al., 2000; Xu et al., 2010). The coupling reaction of with chloromercuriferrocene and 3,6-dichloropyridazine readily afforded the title compound.
There are two molecules in the asymmetric unit(Fig.1). The two cyclopentadienyl rings are almost parallel with dihedral angles of 2.16 (4)° and 2.71 (5)° for molecules containing Fe2 or Fe1, respectively. The dihedral angle between the pyridazinyl and substituted cyclopentadienyl ring is 9.65 (5)° and 11.53 (8)° for molecules containing Fe1 or Fe2, respectively. Intermolecular C—H···N hydrogen bonds construct a chain along the c axis direction (Fig.2).
For the synthesis of the title compound, see: Xu et al. (2012). For applications of organomercury compounds, see: Beletskaya et al. (2001); Tsvetkov et al. (2000); Xu et al. (2010); For palladium-catalysed reactions, see: Meijere & Diederich (2004).
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level. | |
Fig. 2. The crystal packing of the molecules viewed down c axis. |
[Fe(C5H5)(C9H6ClN2)] | F(000) = 2432 |
Mr = 298.55 | Dx = 1.611 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.5488 (19) Å | Cell parameters from 5464 reflections |
b = 12.3788 (6) Å | θ = 3.1–26.3° |
c = 23.043 (2) Å | µ = 1.42 mm−1 |
β = 122.843 (13)° | T = 291 K |
V = 4924.5 (7) Å3 | Block, brown |
Z = 16 | 0.30 × 0.30 × 0.25 mm |
Oxford Diffraction Xcalibur Eos Gemini diffractometer | 4575 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3783 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 16.2312 pixels mm-1 | θmax = 25.5°, θmin = 3.2° |
ω scans | h = −23→24 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −14→14 |
Tmin = 0.675, Tmax = 0.718 | l = −27→27 |
18413 measured reflections |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0332P)2 + 3.3249P] where P = (Fo2 + 2Fc2)/3 |
4575 reflections | (Δ/σ)max = 0.001 |
325 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
[Fe(C5H5)(C9H6ClN2)] | V = 4924.5 (7) Å3 |
Mr = 298.55 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 20.5488 (19) Å | µ = 1.42 mm−1 |
b = 12.3788 (6) Å | T = 291 K |
c = 23.043 (2) Å | 0.30 × 0.30 × 0.25 mm |
β = 122.843 (13)° |
Oxford Diffraction Xcalibur Eos Gemini diffractometer | 4575 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 3783 reflections with I > 2σ(I) |
Tmin = 0.675, Tmax = 0.718 | Rint = 0.032 |
18413 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.36 e Å−3 |
4575 reflections | Δρmin = −0.23 e Å−3 |
325 parameters |
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 | 0.542789 (17) | 0.30107 (3) | 0.582945 (16) | 0.03750 (11) | |
Fe2 | 0.203696 (17) | 0.43834 (2) | 0.410109 (15) | 0.03501 (10) | |
Cl1 | 0.65041 (5) | −0.24694 (6) | 0.71490 (4) | 0.0727 (2) | |
Cl2 | 0.11431 (5) | 0.99199 (6) | 0.30309 (4) | 0.0690 (2) | |
N1 | 0.52234 (11) | −0.00916 (17) | 0.60350 (11) | 0.0485 (5) | |
N2 | 0.54980 (12) | −0.09968 (17) | 0.64197 (12) | 0.0514 (5) | |
N3 | 0.23719 (10) | 0.74910 (16) | 0.41199 (10) | 0.0422 (5) | |
N4 | 0.21252 (11) | 0.84273 (16) | 0.37651 (11) | 0.0458 (5) | |
C1 | 0.53402 (12) | 0.14578 (19) | 0.54950 (12) | 0.0404 (5) | |
C2 | 0.56826 (14) | 0.2140 (2) | 0.52259 (12) | 0.0458 (6) | |
H2 | 0.6197 | 0.2050 | 0.5301 | 0.055* | |
C3 | 0.51425 (15) | 0.2960 (2) | 0.48304 (13) | 0.0528 (7) | |
H3 | 0.5222 | 0.3545 | 0.4589 | 0.063* | |
C4 | 0.44721 (14) | 0.2807 (2) | 0.48506 (13) | 0.0528 (7) | |
H4 | 0.4010 | 0.3267 | 0.4626 | 0.063* | |
C5 | 0.45863 (13) | 0.1893 (2) | 0.52575 (13) | 0.0456 (6) | |
H5 | 0.4217 | 0.1603 | 0.5362 | 0.055* | |
C6 | 0.5420 (2) | 0.3381 (3) | 0.66884 (17) | 0.0745 (10) | |
H6 | 0.5080 | 0.3067 | 0.6820 | 0.089* | |
C7 | 0.6158 (2) | 0.2982 (2) | 0.68728 (14) | 0.0697 (9) | |
H7 | 0.6417 | 0.2342 | 0.7155 | 0.084* | |
C8 | 0.64510 (15) | 0.3671 (2) | 0.65830 (14) | 0.0572 (7) | |
H8 | 0.6951 | 0.3597 | 0.6627 | 0.069* | |
C9 | 0.59049 (16) | 0.4488 (2) | 0.62266 (15) | 0.0577 (7) | |
H9 | 0.5955 | 0.5079 | 0.5971 | 0.069* | |
C10 | 0.52710 (17) | 0.4316 (2) | 0.62874 (16) | 0.0647 (8) | |
H10 | 0.4805 | 0.4765 | 0.6084 | 0.078* | |
C11 | 0.56917 (12) | 0.05099 (18) | 0.59310 (12) | 0.0383 (5) | |
C12 | 0.64703 (13) | 0.0226 (2) | 0.62229 (13) | 0.0440 (6) | |
H12 | 0.6793 | 0.0657 | 0.6153 | 0.053* | |
C13 | 0.67469 (14) | −0.0690 (2) | 0.66087 (13) | 0.0472 (6) | |
H13 | 0.7258 | −0.0911 | 0.6810 | 0.057* | |
C14 | 0.62236 (14) | −0.12723 (19) | 0.66835 (12) | 0.0442 (6) | |
C15 | 0.21916 (12) | 0.58613 (18) | 0.45514 (11) | 0.0361 (5) | |
C16 | 0.18188 (13) | 0.51278 (19) | 0.47649 (11) | 0.0399 (5) | |
H16 | 0.1308 | 0.5228 | 0.4695 | 0.048* | |
C17 | 0.23183 (13) | 0.4242 (2) | 0.50975 (12) | 0.0444 (6) | |
H17 | 0.2209 | 0.3615 | 0.5292 | 0.053* | |
C18 | 0.29996 (13) | 0.4399 (2) | 0.50910 (12) | 0.0453 (6) | |
H18 | 0.3440 | 0.3902 | 0.5279 | 0.054* | |
C19 | 0.29259 (12) | 0.53913 (19) | 0.47570 (11) | 0.0412 (5) | |
H19 | 0.3308 | 0.5702 | 0.4675 | 0.049* | |
C20 | 0.20433 (19) | 0.4178 (3) | 0.32253 (14) | 0.0656 (8) | |
H20 | 0.2404 | 0.4514 | 0.3126 | 0.079* | |
C21 | 0.21428 (17) | 0.3175 (2) | 0.35522 (14) | 0.0594 (7) | |
H21 | 0.2587 | 0.2690 | 0.3723 | 0.071* | |
C22 | 0.14951 (16) | 0.2994 (2) | 0.35885 (13) | 0.0562 (7) | |
H22 | 0.1410 | 0.2358 | 0.3793 | 0.067* | |
C23 | 0.09880 (15) | 0.3871 (2) | 0.32879 (13) | 0.0564 (7) | |
H23 | 0.0487 | 0.3953 | 0.3241 | 0.068* | |
C24 | 0.13262 (18) | 0.4609 (2) | 0.30618 (13) | 0.0621 (8) | |
H24 | 0.1102 | 0.5299 | 0.2829 | 0.074* | |
C25 | 0.18747 (12) | 0.68643 (17) | 0.41683 (11) | 0.0343 (5) | |
C26 | 0.10951 (13) | 0.71658 (19) | 0.38661 (12) | 0.0427 (6) | |
H26 | 0.0754 | 0.6723 | 0.3905 | 0.051* | |
C27 | 0.08504 (14) | 0.8115 (2) | 0.35173 (13) | 0.0470 (6) | |
H27 | 0.0342 | 0.8353 | 0.3312 | 0.056* | |
C28 | 0.14001 (14) | 0.87131 (19) | 0.34830 (12) | 0.0424 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.03557 (18) | 0.03842 (19) | 0.03580 (19) | −0.00429 (14) | 0.01758 (15) | −0.00388 (14) |
Fe2 | 0.03542 (18) | 0.03567 (19) | 0.03032 (18) | −0.00343 (13) | 0.01547 (14) | −0.00137 (14) |
Cl1 | 0.0749 (5) | 0.0669 (5) | 0.0773 (5) | −0.0009 (4) | 0.0419 (4) | 0.0199 (4) |
Cl2 | 0.0785 (5) | 0.0568 (4) | 0.0694 (5) | 0.0043 (4) | 0.0386 (4) | 0.0203 (4) |
N1 | 0.0378 (11) | 0.0504 (13) | 0.0625 (14) | −0.0083 (9) | 0.0306 (10) | −0.0079 (11) |
N2 | 0.0472 (12) | 0.0534 (13) | 0.0617 (14) | −0.0125 (10) | 0.0348 (11) | −0.0065 (11) |
N3 | 0.0360 (10) | 0.0450 (12) | 0.0488 (12) | −0.0090 (9) | 0.0251 (9) | −0.0034 (10) |
N4 | 0.0474 (12) | 0.0457 (12) | 0.0513 (13) | −0.0103 (10) | 0.0312 (10) | −0.0015 (10) |
C1 | 0.0343 (12) | 0.0448 (13) | 0.0409 (13) | −0.0060 (10) | 0.0195 (10) | −0.0123 (11) |
C2 | 0.0416 (13) | 0.0578 (16) | 0.0394 (13) | −0.0023 (12) | 0.0230 (11) | −0.0063 (12) |
C3 | 0.0499 (15) | 0.0681 (18) | 0.0377 (14) | 0.0025 (13) | 0.0219 (12) | 0.0024 (13) |
C4 | 0.0393 (13) | 0.0653 (17) | 0.0389 (14) | 0.0044 (12) | 0.0116 (11) | −0.0041 (13) |
C5 | 0.0331 (12) | 0.0510 (15) | 0.0468 (14) | −0.0087 (11) | 0.0179 (11) | −0.0134 (12) |
C6 | 0.101 (3) | 0.080 (2) | 0.067 (2) | −0.046 (2) | 0.061 (2) | −0.0397 (18) |
C7 | 0.099 (2) | 0.0494 (17) | 0.0309 (14) | −0.0075 (16) | 0.0161 (15) | −0.0060 (13) |
C8 | 0.0437 (14) | 0.0570 (17) | 0.0541 (17) | −0.0112 (13) | 0.0154 (13) | −0.0136 (14) |
C9 | 0.0603 (17) | 0.0383 (14) | 0.0687 (19) | −0.0101 (13) | 0.0312 (15) | −0.0052 (13) |
C10 | 0.0603 (18) | 0.0564 (18) | 0.075 (2) | −0.0028 (14) | 0.0349 (16) | −0.0246 (16) |
C11 | 0.0355 (12) | 0.0412 (13) | 0.0429 (13) | −0.0113 (10) | 0.0242 (10) | −0.0158 (11) |
C12 | 0.0381 (12) | 0.0475 (14) | 0.0550 (15) | −0.0094 (11) | 0.0308 (12) | −0.0069 (12) |
C13 | 0.0402 (13) | 0.0500 (15) | 0.0568 (16) | −0.0018 (11) | 0.0298 (12) | −0.0032 (12) |
C14 | 0.0488 (14) | 0.0449 (14) | 0.0423 (14) | −0.0083 (11) | 0.0269 (12) | −0.0082 (11) |
C15 | 0.0351 (12) | 0.0399 (12) | 0.0342 (12) | −0.0085 (10) | 0.0194 (10) | −0.0068 (10) |
C16 | 0.0400 (12) | 0.0450 (13) | 0.0384 (13) | −0.0051 (10) | 0.0237 (11) | −0.0044 (11) |
C17 | 0.0470 (14) | 0.0505 (15) | 0.0320 (12) | −0.0020 (11) | 0.0189 (11) | 0.0037 (11) |
C18 | 0.0376 (12) | 0.0543 (15) | 0.0327 (12) | 0.0034 (11) | 0.0117 (10) | 0.0004 (11) |
C19 | 0.0327 (12) | 0.0509 (14) | 0.0370 (13) | −0.0087 (10) | 0.0169 (10) | −0.0086 (11) |
C20 | 0.084 (2) | 0.077 (2) | 0.0485 (16) | −0.0356 (18) | 0.0438 (16) | −0.0257 (15) |
C21 | 0.0629 (18) | 0.0566 (17) | 0.0503 (16) | 0.0016 (14) | 0.0252 (14) | −0.0178 (14) |
C22 | 0.0673 (18) | 0.0392 (14) | 0.0451 (15) | −0.0158 (13) | 0.0194 (14) | −0.0058 (12) |
C23 | 0.0431 (14) | 0.0668 (18) | 0.0394 (14) | −0.0093 (13) | 0.0094 (11) | −0.0068 (13) |
C24 | 0.086 (2) | 0.0470 (15) | 0.0294 (13) | 0.0004 (15) | 0.0158 (14) | 0.0025 (12) |
C25 | 0.0355 (11) | 0.0377 (12) | 0.0346 (12) | −0.0112 (9) | 0.0221 (10) | −0.0112 (10) |
C26 | 0.0373 (12) | 0.0453 (14) | 0.0527 (15) | −0.0080 (11) | 0.0291 (11) | −0.0032 (12) |
C27 | 0.0376 (13) | 0.0530 (15) | 0.0528 (15) | 0.0003 (11) | 0.0260 (12) | 0.0006 (12) |
C28 | 0.0508 (14) | 0.0411 (13) | 0.0380 (13) | −0.0037 (11) | 0.0259 (11) | −0.0019 (11) |
Fe1—C7 | 2.030 (3) | C6—C7 | 1.423 (4) |
Fe1—C8 | 2.036 (3) | C6—H6 | 0.9800 |
Fe1—C2 | 2.039 (2) | C7—C8 | 1.405 (4) |
Fe1—C6 | 2.041 (3) | C7—H7 | 0.9800 |
Fe1—C9 | 2.042 (3) | C8—C9 | 1.398 (4) |
Fe1—C5 | 2.042 (2) | C8—H8 | 0.9800 |
Fe1—C1 | 2.042 (2) | C9—C10 | 1.400 (4) |
Fe1—C3 | 2.045 (3) | C9—H9 | 0.9800 |
Fe1—C10 | 2.049 (3) | C10—H10 | 0.9800 |
Fe1—C4 | 2.050 (2) | C11—C12 | 1.403 (3) |
Fe2—C16 | 2.033 (2) | C12—C13 | 1.360 (3) |
Fe2—C24 | 2.038 (3) | C12—H12 | 0.9300 |
Fe2—C20 | 2.041 (3) | C13—C14 | 1.381 (3) |
Fe2—C22 | 2.041 (2) | C13—H13 | 0.9300 |
Fe2—C15 | 2.041 (2) | C15—C16 | 1.436 (3) |
Fe2—C23 | 2.044 (2) | C15—C19 | 1.437 (3) |
Fe2—C21 | 2.045 (3) | C15—C25 | 1.456 (3) |
Fe2—C19 | 2.045 (2) | C16—C17 | 1.411 (3) |
Fe2—C17 | 2.049 (2) | C16—H16 | 0.9800 |
Fe2—C18 | 2.055 (2) | C17—C18 | 1.422 (3) |
Cl1—C14 | 1.734 (3) | C17—H17 | 0.9800 |
Cl2—C28 | 1.732 (2) | C18—C19 | 1.413 (3) |
N1—C11 | 1.337 (3) | C18—H18 | 0.9800 |
N1—N2 | 1.348 (3) | C19—H19 | 0.9800 |
N2—C14 | 1.314 (3) | C20—C21 | 1.408 (4) |
N3—C25 | 1.335 (3) | C20—C24 | 1.413 (4) |
N3—N4 | 1.349 (3) | C20—H20 | 0.9800 |
N4—C28 | 1.310 (3) | C21—C22 | 1.396 (4) |
C1—C2 | 1.437 (3) | C21—H21 | 0.9800 |
C1—C5 | 1.438 (3) | C22—C23 | 1.400 (4) |
C1—C11 | 1.456 (3) | C22—H22 | 0.9800 |
C2—C3 | 1.413 (4) | C23—C24 | 1.408 (4) |
C2—H2 | 0.9800 | C23—H23 | 0.9800 |
C3—C4 | 1.416 (4) | C24—H24 | 0.9800 |
C3—H3 | 0.9800 | C25—C26 | 1.407 (3) |
C4—C5 | 1.405 (4) | C26—C27 | 1.357 (3) |
C4—H4 | 0.9800 | C26—H26 | 0.9300 |
C5—H5 | 0.9800 | C27—C28 | 1.388 (3) |
C6—C10 | 1.407 (4) | C27—H27 | 0.9300 |
C7—Fe1—C8 | 40.43 (12) | C4—C5—Fe1 | 70.22 (14) |
C7—Fe1—C2 | 120.04 (12) | C1—C5—Fe1 | 69.38 (12) |
C8—Fe1—C2 | 105.41 (11) | C4—C5—H5 | 125.9 |
C7—Fe1—C6 | 40.93 (13) | C1—C5—H5 | 125.9 |
C8—Fe1—C6 | 68.32 (12) | Fe1—C5—H5 | 125.9 |
C2—Fe1—C6 | 156.98 (14) | C10—C6—C7 | 107.3 (3) |
C7—Fe1—C9 | 67.54 (12) | C10—C6—Fe1 | 70.17 (17) |
C8—Fe1—C9 | 40.12 (11) | C7—C6—Fe1 | 69.10 (16) |
C2—Fe1—C9 | 122.72 (11) | C10—C6—H6 | 126.3 |
C6—Fe1—C9 | 67.57 (12) | C7—C6—H6 | 126.3 |
C7—Fe1—C5 | 125.15 (12) | Fe1—C6—H6 | 126.3 |
C8—Fe1—C5 | 160.73 (11) | C8—C7—C6 | 108.1 (3) |
C2—Fe1—C5 | 69.05 (10) | C8—C7—Fe1 | 70.01 (15) |
C6—Fe1—C5 | 109.19 (11) | C6—C7—Fe1 | 69.96 (17) |
C9—Fe1—C5 | 158.25 (11) | C8—C7—H7 | 126.0 |
C7—Fe1—C1 | 106.73 (11) | C6—C7—H7 | 126.0 |
C8—Fe1—C1 | 122.61 (10) | Fe1—C7—H7 | 126.0 |
C2—Fe1—C1 | 41.24 (9) | C9—C8—C7 | 107.7 (3) |
C6—Fe1—C1 | 122.15 (12) | C9—C8—Fe1 | 70.17 (15) |
C9—Fe1—C1 | 159.18 (10) | C7—C8—Fe1 | 69.55 (15) |
C5—Fe1—C1 | 41.24 (9) | C9—C8—H8 | 126.2 |
C7—Fe1—C3 | 155.42 (13) | C7—C8—H8 | 126.2 |
C8—Fe1—C3 | 120.36 (12) | Fe1—C8—H8 | 126.2 |
C2—Fe1—C3 | 40.47 (10) | C8—C9—C10 | 109.0 (3) |
C6—Fe1—C3 | 161.87 (14) | C8—C9—Fe1 | 69.71 (15) |
C9—Fe1—C3 | 107.86 (12) | C10—C9—Fe1 | 70.26 (15) |
C5—Fe1—C3 | 68.12 (11) | C8—C9—H9 | 125.5 |
C1—Fe1—C3 | 68.52 (10) | C10—C9—H9 | 125.5 |
C7—Fe1—C10 | 67.98 (13) | Fe1—C9—H9 | 125.5 |
C8—Fe1—C10 | 67.80 (11) | C9—C10—C6 | 108.0 (3) |
C2—Fe1—C10 | 159.77 (12) | C9—C10—Fe1 | 69.72 (15) |
C6—Fe1—C10 | 40.25 (13) | C6—C10—Fe1 | 69.58 (16) |
C9—Fe1—C10 | 40.03 (11) | C9—C10—H10 | 126.0 |
C5—Fe1—C10 | 123.52 (11) | C6—C10—H10 | 126.0 |
C1—Fe1—C10 | 158.49 (11) | Fe1—C10—H10 | 126.0 |
C3—Fe1—C10 | 125.08 (12) | N1—C11—C12 | 121.3 (2) |
C7—Fe1—C4 | 162.27 (13) | N1—C11—C1 | 115.9 (2) |
C8—Fe1—C4 | 156.62 (12) | C12—C11—C1 | 122.9 (2) |
C2—Fe1—C4 | 68.39 (10) | C13—C12—C11 | 119.1 (2) |
C6—Fe1—C4 | 125.99 (13) | C13—C12—H12 | 120.5 |
C9—Fe1—C4 | 122.96 (11) | C11—C12—H12 | 120.5 |
C5—Fe1—C4 | 40.17 (10) | C12—C13—C14 | 116.0 (2) |
C1—Fe1—C4 | 68.47 (10) | C12—C13—H13 | 122.0 |
C3—Fe1—C4 | 40.46 (10) | C14—C13—H13 | 122.0 |
C10—Fe1—C4 | 109.84 (12) | N2—C14—C13 | 124.9 (2) |
C16—Fe2—C24 | 120.79 (11) | N2—C14—Cl1 | 114.90 (18) |
C16—Fe2—C20 | 157.30 (12) | C13—C14—Cl1 | 120.2 (2) |
C24—Fe2—C20 | 40.53 (12) | C16—C15—C19 | 106.9 (2) |
C16—Fe2—C22 | 122.93 (11) | C16—C15—C25 | 126.9 (2) |
C24—Fe2—C22 | 67.50 (11) | C19—C15—C25 | 126.12 (19) |
C20—Fe2—C22 | 67.47 (11) | C16—C15—Fe2 | 69.06 (12) |
C16—Fe2—C15 | 41.28 (9) | C19—C15—Fe2 | 69.57 (13) |
C24—Fe2—C15 | 106.80 (10) | C25—C15—Fe2 | 124.11 (15) |
C20—Fe2—C15 | 122.10 (11) | C17—C16—C15 | 108.2 (2) |
C22—Fe2—C15 | 159.23 (10) | C17—C16—Fe2 | 70.37 (13) |
C16—Fe2—C23 | 106.09 (10) | C15—C16—Fe2 | 69.67 (12) |
C24—Fe2—C23 | 40.36 (11) | C17—C16—H16 | 125.9 |
C20—Fe2—C23 | 67.91 (12) | C15—C16—H16 | 125.9 |
C22—Fe2—C23 | 40.09 (11) | Fe2—C16—H16 | 125.9 |
C15—Fe2—C23 | 122.70 (10) | C16—C17—C18 | 108.5 (2) |
C16—Fe2—C21 | 159.65 (11) | C16—C17—Fe2 | 69.19 (13) |
C24—Fe2—C21 | 67.82 (12) | C18—C17—Fe2 | 69.96 (13) |
C20—Fe2—C21 | 40.32 (12) | C16—C17—H17 | 125.7 |
C22—Fe2—C21 | 39.96 (11) | C18—C17—H17 | 125.7 |
C15—Fe2—C21 | 158.49 (11) | Fe2—C17—H17 | 125.7 |
C23—Fe2—C21 | 67.61 (12) | C19—C18—C17 | 108.0 (2) |
C16—Fe2—C19 | 68.93 (9) | C19—C18—Fe2 | 69.48 (13) |
C24—Fe2—C19 | 124.63 (11) | C17—C18—Fe2 | 69.50 (13) |
C20—Fe2—C19 | 108.94 (10) | C19—C18—H18 | 126.0 |
C22—Fe2—C19 | 158.41 (11) | C17—C18—H18 | 126.0 |
C15—Fe2—C19 | 41.17 (9) | Fe2—C18—H18 | 126.0 |
C23—Fe2—C19 | 160.37 (11) | C18—C19—C15 | 108.3 (2) |
C21—Fe2—C19 | 123.45 (11) | C18—C19—Fe2 | 70.20 (13) |
C16—Fe2—C17 | 40.45 (9) | C15—C19—Fe2 | 69.26 (12) |
C24—Fe2—C17 | 156.29 (12) | C18—C19—H19 | 125.8 |
C20—Fe2—C17 | 161.48 (12) | C15—C19—H19 | 125.8 |
C22—Fe2—C17 | 108.07 (10) | Fe2—C19—H19 | 125.8 |
C15—Fe2—C17 | 68.63 (9) | C21—C20—C24 | 107.7 (3) |
C23—Fe2—C17 | 121.13 (11) | C21—C20—Fe2 | 70.00 (16) |
C21—Fe2—C17 | 124.78 (11) | C24—C20—Fe2 | 69.61 (15) |
C19—Fe2—C17 | 68.16 (9) | C21—C20—H20 | 126.2 |
C16—Fe2—C18 | 68.46 (9) | C24—C20—H20 | 126.2 |
C24—Fe2—C18 | 161.48 (12) | Fe2—C20—H20 | 126.2 |
C20—Fe2—C18 | 125.47 (12) | C22—C21—C20 | 107.9 (3) |
C22—Fe2—C18 | 123.02 (10) | C22—C21—Fe2 | 69.87 (15) |
C15—Fe2—C18 | 68.69 (9) | C20—C21—Fe2 | 69.68 (15) |
C23—Fe2—C18 | 157.24 (11) | C22—C21—H21 | 126.1 |
C21—Fe2—C18 | 109.40 (11) | C20—C21—H21 | 126.1 |
C19—Fe2—C18 | 40.33 (9) | Fe2—C21—H21 | 126.1 |
C17—Fe2—C18 | 40.54 (9) | C21—C22—C23 | 108.9 (2) |
C11—N1—N2 | 119.70 (19) | C21—C22—Fe2 | 70.17 (14) |
C14—N2—N1 | 119.0 (2) | C23—C22—Fe2 | 70.07 (14) |
C25—N3—N4 | 119.79 (19) | C21—C22—H22 | 125.6 |
C28—N4—N3 | 119.03 (18) | C23—C22—H22 | 125.6 |
C2—C1—C5 | 107.1 (2) | Fe2—C22—H22 | 125.6 |
C2—C1—C11 | 126.5 (2) | C22—C23—C24 | 107.6 (3) |
C5—C1—C11 | 126.4 (2) | C22—C23—Fe2 | 69.84 (14) |
C2—C1—Fe1 | 69.28 (13) | C24—C23—Fe2 | 69.57 (15) |
C5—C1—Fe1 | 69.38 (13) | C22—C23—H23 | 126.2 |
C11—C1—Fe1 | 126.07 (16) | C24—C23—H23 | 126.2 |
C3—C2—C1 | 107.7 (2) | Fe2—C23—H23 | 126.2 |
C3—C2—Fe1 | 69.98 (14) | C23—C24—C20 | 108.0 (3) |
C1—C2—Fe1 | 69.49 (13) | C23—C24—Fe2 | 70.07 (14) |
C3—C2—H2 | 126.2 | C20—C24—Fe2 | 69.86 (15) |
C1—C2—H2 | 126.2 | C23—C24—H24 | 126.0 |
Fe1—C2—H2 | 126.2 | C20—C24—H24 | 126.0 |
C2—C3—C4 | 108.7 (2) | Fe2—C24—H24 | 126.0 |
C2—C3—Fe1 | 69.55 (14) | N3—C25—C26 | 121.5 (2) |
C4—C3—Fe1 | 69.96 (14) | N3—C25—C15 | 115.79 (19) |
C2—C3—H3 | 125.7 | C26—C25—C15 | 122.74 (19) |
C4—C3—H3 | 125.7 | C27—C26—C25 | 118.6 (2) |
Fe1—C3—H3 | 125.7 | C27—C26—H26 | 120.7 |
C5—C4—C3 | 108.4 (2) | C25—C26—H26 | 120.7 |
C5—C4—Fe1 | 69.61 (14) | C26—C27—C28 | 116.4 (2) |
C3—C4—Fe1 | 69.57 (14) | C26—C27—H27 | 121.8 |
C5—C4—H4 | 125.8 | C28—C27—H27 | 121.8 |
C3—C4—H4 | 125.8 | N4—C28—C27 | 124.7 (2) |
Fe1—C4—H4 | 125.8 | N4—C28—Cl2 | 115.15 (17) |
C4—C5—C1 | 108.1 (2) | C27—C28—Cl2 | 120.14 (19) |
C11—N1—N2—C14 | −0.3 (3) | C12—C13—C14—Cl1 | 178.63 (18) |
C25—N3—N4—C28 | 1.1 (3) | C24—Fe2—C15—C16 | 117.82 (16) |
C7—Fe1—C1—C2 | −116.75 (17) | C20—Fe2—C15—C16 | 159.42 (15) |
C8—Fe1—C1—C2 | −75.44 (18) | C22—Fe2—C15—C16 | 47.2 (3) |
C6—Fe1—C1—C2 | −158.78 (17) | C23—Fe2—C15—C16 | 76.58 (17) |
C9—Fe1—C1—C2 | −46.1 (4) | C21—Fe2—C15—C16 | −170.2 (3) |
C5—Fe1—C1—C2 | 118.6 (2) | C19—Fe2—C15—C16 | −118.36 (19) |
C3—Fe1—C1—C2 | 37.70 (14) | C17—Fe2—C15—C16 | −37.53 (13) |
C10—Fe1—C1—C2 | 171.0 (3) | C18—Fe2—C15—C16 | −81.20 (14) |
C4—Fe1—C1—C2 | 81.34 (15) | C16—Fe2—C15—C19 | 118.36 (19) |
C7—Fe1—C1—C5 | 124.68 (18) | C24—Fe2—C15—C19 | −123.82 (16) |
C8—Fe1—C1—C5 | 165.98 (16) | C20—Fe2—C15—C19 | −82.22 (18) |
C2—Fe1—C1—C5 | −118.6 (2) | C22—Fe2—C15—C19 | 165.5 (3) |
C6—Fe1—C1—C5 | 82.64 (19) | C23—Fe2—C15—C19 | −165.06 (14) |
C9—Fe1—C1—C5 | −164.7 (3) | C21—Fe2—C15—C19 | −51.8 (3) |
C3—Fe1—C1—C5 | −80.88 (16) | C17—Fe2—C15—C19 | 80.83 (14) |
C10—Fe1—C1—C5 | 52.4 (4) | C18—Fe2—C15—C19 | 37.16 (13) |
C4—Fe1—C1—C5 | −37.24 (15) | C16—Fe2—C15—C25 | −121.1 (2) |
C7—Fe1—C1—C11 | 4.0 (2) | C24—Fe2—C15—C25 | −3.3 (2) |
C8—Fe1—C1—C11 | 45.3 (2) | C20—Fe2—C15—C25 | 38.3 (2) |
C2—Fe1—C1—C11 | 120.8 (2) | C22—Fe2—C15—C25 | −74.0 (3) |
C6—Fe1—C1—C11 | −38.0 (2) | C23—Fe2—C15—C25 | −44.6 (2) |
C9—Fe1—C1—C11 | 74.7 (4) | C21—Fe2—C15—C25 | 68.7 (3) |
C5—Fe1—C1—C11 | −120.6 (3) | C19—Fe2—C15—C25 | 120.5 (2) |
C3—Fe1—C1—C11 | 158.5 (2) | C17—Fe2—C15—C25 | −158.7 (2) |
C10—Fe1—C1—C11 | −68.2 (4) | C18—Fe2—C15—C25 | 157.7 (2) |
C4—Fe1—C1—C11 | −157.9 (2) | C19—C15—C16—C17 | 0.6 (2) |
C5—C1—C2—C3 | −0.5 (3) | C25—C15—C16—C17 | 177.7 (2) |
C11—C1—C2—C3 | 180.0 (2) | Fe2—C15—C16—C17 | 60.09 (16) |
Fe1—C1—C2—C3 | −59.82 (17) | C19—C15—C16—Fe2 | −59.53 (15) |
C5—C1—C2—Fe1 | 59.31 (15) | C25—C15—C16—Fe2 | 117.6 (2) |
C11—C1—C2—Fe1 | −120.2 (2) | C24—Fe2—C16—C17 | 160.71 (15) |
C7—Fe1—C2—C3 | −160.17 (16) | C20—Fe2—C16—C17 | −169.5 (2) |
C8—Fe1—C2—C3 | −118.99 (17) | C22—Fe2—C16—C17 | 79.03 (17) |
C6—Fe1—C2—C3 | 170.4 (3) | C15—Fe2—C16—C17 | −119.01 (19) |
C9—Fe1—C2—C3 | −78.97 (18) | C23—Fe2—C16—C17 | 119.41 (15) |
C5—Fe1—C2—C3 | 80.45 (16) | C21—Fe2—C16—C17 | 50.7 (3) |
C1—Fe1—C2—C3 | 118.8 (2) | C19—Fe2—C16—C17 | −80.64 (15) |
C10—Fe1—C2—C3 | −51.7 (4) | C18—Fe2—C16—C17 | −37.22 (14) |
C4—Fe1—C2—C3 | 37.20 (16) | C24—Fe2—C16—C15 | −80.28 (16) |
C7—Fe1—C2—C1 | 81.07 (17) | C20—Fe2—C16—C15 | −50.5 (3) |
C8—Fe1—C2—C1 | 122.25 (15) | C22—Fe2—C16—C15 | −161.95 (13) |
C6—Fe1—C2—C1 | 51.6 (3) | C23—Fe2—C16—C15 | −121.58 (14) |
C9—Fe1—C2—C1 | 162.27 (14) | C21—Fe2—C16—C15 | 169.7 (3) |
C5—Fe1—C2—C1 | −38.31 (14) | C19—Fe2—C16—C15 | 38.37 (13) |
C3—Fe1—C2—C1 | −118.8 (2) | C17—Fe2—C16—C15 | 119.01 (19) |
C10—Fe1—C2—C1 | −170.4 (3) | C18—Fe2—C16—C15 | 81.80 (14) |
C4—Fe1—C2—C1 | −81.56 (15) | C15—C16—C17—C18 | −0.6 (3) |
C1—C2—C3—C4 | 0.3 (3) | Fe2—C16—C17—C18 | 59.06 (16) |
Fe1—C2—C3—C4 | −59.20 (18) | C15—C16—C17—Fe2 | −59.65 (15) |
C1—C2—C3—Fe1 | 59.51 (16) | C24—Fe2—C17—C16 | −44.9 (3) |
C7—Fe1—C3—C2 | 44.9 (3) | C20—Fe2—C17—C16 | 167.2 (3) |
C8—Fe1—C3—C2 | 77.75 (18) | C22—Fe2—C17—C16 | −119.92 (15) |
C6—Fe1—C3—C2 | −167.9 (3) | C15—Fe2—C17—C16 | 38.28 (13) |
C9—Fe1—C3—C2 | 119.82 (16) | C23—Fe2—C17—C16 | −77.91 (17) |
C5—Fe1—C3—C2 | −82.93 (16) | C21—Fe2—C17—C16 | −160.88 (15) |
C1—Fe1—C3—C2 | −38.39 (14) | C19—Fe2—C17—C16 | 82.71 (15) |
C10—Fe1—C3—C2 | 160.64 (15) | C18—Fe2—C17—C16 | 120.1 (2) |
C4—Fe1—C3—C2 | −120.0 (2) | C16—Fe2—C17—C18 | −120.1 (2) |
C7—Fe1—C3—C4 | 164.9 (3) | C24—Fe2—C17—C18 | −164.9 (2) |
C8—Fe1—C3—C4 | −162.27 (16) | C20—Fe2—C17—C18 | 47.2 (4) |
C2—Fe1—C3—C4 | 120.0 (2) | C22—Fe2—C17—C18 | 120.03 (16) |
C6—Fe1—C3—C4 | −47.9 (4) | C15—Fe2—C17—C18 | −81.78 (15) |
C9—Fe1—C3—C4 | −120.20 (17) | C23—Fe2—C17—C18 | 162.03 (15) |
C5—Fe1—C3—C4 | 37.05 (15) | C21—Fe2—C17—C18 | 79.06 (18) |
C1—Fe1—C3—C4 | 81.59 (16) | C19—Fe2—C17—C18 | −37.34 (14) |
C10—Fe1—C3—C4 | −79.38 (19) | C16—C17—C18—C19 | 0.4 (3) |
C2—C3—C4—C5 | 0.0 (3) | Fe2—C17—C18—C19 | 58.98 (16) |
Fe1—C3—C4—C5 | −58.93 (17) | C16—C17—C18—Fe2 | −58.58 (16) |
C2—C3—C4—Fe1 | 58.95 (18) | C16—Fe2—C18—C19 | −82.41 (15) |
C7—Fe1—C4—C5 | −39.2 (4) | C24—Fe2—C18—C19 | 41.3 (4) |
C8—Fe1—C4—C5 | 161.4 (2) | C20—Fe2—C18—C19 | 77.08 (18) |
C2—Fe1—C4—C5 | 82.70 (16) | C22—Fe2—C18—C19 | 161.46 (15) |
C6—Fe1—C4—C5 | −76.7 (2) | C15—Fe2—C18—C19 | −37.91 (13) |
C9—Fe1—C4—C5 | −161.44 (15) | C23—Fe2—C18—C19 | −162.6 (3) |
C1—Fe1—C4—C5 | 38.20 (14) | C21—Fe2—C18—C19 | 119.22 (15) |
C3—Fe1—C4—C5 | 119.9 (2) | C17—Fe2—C18—C19 | −119.5 (2) |
C10—Fe1—C4—C5 | −118.86 (16) | C16—Fe2—C18—C17 | 37.13 (14) |
C7—Fe1—C4—C3 | −159.2 (4) | C24—Fe2—C18—C17 | 160.8 (3) |
C8—Fe1—C4—C3 | 41.5 (3) | C20—Fe2—C18—C17 | −163.38 (16) |
C2—Fe1—C4—C3 | −37.21 (16) | C22—Fe2—C18—C17 | −79.00 (18) |
C6—Fe1—C4—C3 | 163.43 (18) | C15—Fe2—C18—C17 | 81.63 (15) |
C9—Fe1—C4—C3 | 78.64 (19) | C23—Fe2—C18—C17 | −43.0 (3) |
C5—Fe1—C4—C3 | −119.9 (2) | C21—Fe2—C18—C17 | −121.24 (16) |
C1—Fe1—C4—C3 | −81.71 (16) | C19—Fe2—C18—C17 | 119.5 (2) |
C10—Fe1—C4—C3 | 121.23 (17) | C17—C18—C19—C15 | 0.0 (3) |
C3—C4—C5—C1 | −0.3 (3) | Fe2—C18—C19—C15 | 58.95 (15) |
Fe1—C4—C5—C1 | −59.24 (16) | C17—C18—C19—Fe2 | −58.99 (16) |
C3—C4—C5—Fe1 | 58.90 (18) | C16—C15—C19—C18 | −0.3 (2) |
C2—C1—C5—C4 | 0.5 (3) | C25—C15—C19—C18 | −177.5 (2) |
C11—C1—C5—C4 | −180.0 (2) | Fe2—C15—C19—C18 | −59.52 (16) |
Fe1—C1—C5—C4 | 59.77 (17) | C16—C15—C19—Fe2 | 59.20 (15) |
C2—C1—C5—Fe1 | −59.25 (16) | C25—C15—C19—Fe2 | −118.0 (2) |
C11—C1—C5—Fe1 | 120.3 (2) | C16—Fe2—C19—C18 | 81.13 (15) |
C7—Fe1—C5—C4 | 166.37 (17) | C24—Fe2—C19—C18 | −165.25 (16) |
C8—Fe1—C5—C4 | −157.4 (3) | C20—Fe2—C19—C18 | −122.94 (16) |
C2—Fe1—C5—C4 | −80.92 (16) | C22—Fe2—C19—C18 | −46.5 (3) |
C6—Fe1—C5—C4 | 123.53 (18) | C15—Fe2—C19—C18 | 119.60 (19) |
C9—Fe1—C5—C4 | 46.1 (4) | C23—Fe2—C19—C18 | 159.8 (3) |
C1—Fe1—C5—C4 | −119.2 (2) | C21—Fe2—C19—C18 | −80.62 (18) |
C3—Fe1—C5—C4 | −37.31 (15) | C17—Fe2—C19—C18 | 37.53 (14) |
C10—Fe1—C5—C4 | 81.17 (19) | C16—Fe2—C19—C15 | −38.47 (13) |
C7—Fe1—C5—C1 | −74.4 (2) | C24—Fe2—C19—C15 | 75.15 (18) |
C8—Fe1—C5—C1 | −38.2 (4) | C20—Fe2—C19—C15 | 117.46 (16) |
C2—Fe1—C5—C1 | 38.31 (14) | C22—Fe2—C19—C15 | −166.1 (3) |
C6—Fe1—C5—C1 | −117.24 (18) | C23—Fe2—C19—C15 | 40.2 (4) |
C9—Fe1—C5—C1 | 165.3 (3) | C21—Fe2—C19—C15 | 159.78 (15) |
C3—Fe1—C5—C1 | 81.92 (15) | C17—Fe2—C19—C15 | −82.07 (14) |
C10—Fe1—C5—C1 | −159.60 (16) | C18—Fe2—C19—C15 | −119.60 (19) |
C4—Fe1—C5—C1 | 119.2 (2) | C16—Fe2—C20—C21 | −159.7 (2) |
C7—Fe1—C6—C10 | 118.5 (2) | C24—Fe2—C20—C21 | −118.7 (2) |
C8—Fe1—C6—C10 | 80.81 (18) | C22—Fe2—C20—C21 | −37.46 (17) |
C2—Fe1—C6—C10 | 159.0 (2) | C15—Fe2—C20—C21 | 163.35 (16) |
C9—Fe1—C6—C10 | 37.38 (17) | C23—Fe2—C20—C21 | −80.95 (18) |
C5—Fe1—C6—C10 | −119.59 (18) | C19—Fe2—C20—C21 | 119.75 (17) |
C1—Fe1—C6—C10 | −163.40 (16) | C17—Fe2—C20—C21 | 42.1 (4) |
C3—Fe1—C6—C10 | −41.4 (4) | C18—Fe2—C20—C21 | 77.9 (2) |
C4—Fe1—C6—C10 | −77.9 (2) | C16—Fe2—C20—C24 | −41.0 (3) |
C8—Fe1—C6—C7 | −37.65 (17) | C22—Fe2—C20—C24 | 81.23 (18) |
C2—Fe1—C6—C7 | 40.5 (3) | C15—Fe2—C20—C24 | −77.96 (18) |
C9—Fe1—C6—C7 | −81.08 (18) | C23—Fe2—C20—C24 | 37.74 (16) |
C5—Fe1—C6—C7 | 121.94 (17) | C21—Fe2—C20—C24 | 118.7 (2) |
C1—Fe1—C6—C7 | 78.14 (19) | C19—Fe2—C20—C24 | −121.55 (16) |
C3—Fe1—C6—C7 | −159.9 (3) | C17—Fe2—C20—C24 | 160.8 (3) |
C10—Fe1—C6—C7 | −118.5 (2) | C18—Fe2—C20—C24 | −163.38 (16) |
C4—Fe1—C6—C7 | 163.59 (17) | C24—C20—C21—C22 | 0.0 (3) |
C10—C6—C7—C8 | −0.1 (3) | Fe2—C20—C21—C22 | 59.66 (18) |
Fe1—C6—C7—C8 | 59.90 (19) | C24—C20—C21—Fe2 | −59.65 (18) |
C10—C6—C7—Fe1 | −60.03 (19) | C16—Fe2—C21—C22 | 38.4 (4) |
C2—Fe1—C7—C8 | 78.14 (19) | C24—Fe2—C21—C22 | −80.97 (18) |
C6—Fe1—C7—C8 | −118.9 (2) | C20—Fe2—C21—C22 | −119.0 (2) |
C9—Fe1—C7—C8 | −37.75 (17) | C15—Fe2—C21—C22 | −160.4 (2) |
C5—Fe1—C7—C8 | 162.51 (16) | C23—Fe2—C21—C22 | −37.19 (16) |
C1—Fe1—C7—C8 | 120.98 (17) | C19—Fe2—C21—C22 | 161.23 (15) |
C3—Fe1—C7—C8 | 46.2 (3) | C17—Fe2—C21—C22 | 76.05 (19) |
C10—Fe1—C7—C8 | −81.15 (18) | C18—Fe2—C21—C22 | 118.63 (17) |
C4—Fe1—C7—C8 | −167.6 (3) | C16—Fe2—C21—C20 | 157.4 (3) |
C8—Fe1—C7—C6 | 118.9 (2) | C24—Fe2—C21—C20 | 38.00 (17) |
C2—Fe1—C7—C6 | −162.93 (17) | C22—Fe2—C21—C20 | 119.0 (2) |
C9—Fe1—C7—C6 | 81.18 (19) | C15—Fe2—C21—C20 | −41.4 (4) |
C5—Fe1—C7—C6 | −78.6 (2) | C23—Fe2—C21—C20 | 81.78 (19) |
C1—Fe1—C7—C6 | −120.09 (17) | C19—Fe2—C21—C20 | −79.8 (2) |
C3—Fe1—C7—C6 | 165.1 (3) | C17—Fe2—C21—C20 | −164.97 (16) |
C10—Fe1—C7—C6 | 37.78 (17) | C18—Fe2—C21—C20 | −122.40 (18) |
C4—Fe1—C7—C6 | −48.6 (4) | C20—C21—C22—C23 | 0.0 (3) |
C6—C7—C8—C9 | 0.2 (3) | Fe2—C21—C22—C23 | 59.58 (18) |
Fe1—C7—C8—C9 | 60.09 (19) | C20—C21—C22—Fe2 | −59.54 (18) |
C6—C7—C8—Fe1 | −59.86 (19) | C16—Fe2—C22—C21 | −165.08 (16) |
C7—Fe1—C8—C9 | −118.6 (3) | C24—Fe2—C22—C21 | 81.84 (19) |
C2—Fe1—C8—C9 | 122.90 (18) | C20—Fe2—C22—C21 | 37.80 (18) |
C6—Fe1—C8—C9 | −80.5 (2) | C15—Fe2—C22—C21 | 159.7 (3) |
C5—Fe1—C8—C9 | −166.7 (3) | C23—Fe2—C22—C21 | 119.8 (2) |
C1—Fe1—C8—C9 | 164.34 (16) | C19—Fe2—C22—C21 | −46.9 (3) |
C3—Fe1—C8—C9 | 81.8 (2) | C17—Fe2—C22—C21 | −123.02 (17) |
C10—Fe1—C8—C9 | −36.95 (18) | C18—Fe2—C22—C21 | −80.87 (19) |
C4—Fe1—C8—C9 | 51.9 (3) | C16—Fe2—C22—C23 | 75.13 (19) |
C2—Fe1—C8—C7 | −118.51 (19) | C24—Fe2—C22—C23 | −37.94 (17) |
C6—Fe1—C8—C7 | 38.10 (19) | C20—Fe2—C22—C23 | −81.99 (19) |
C9—Fe1—C8—C7 | 118.6 (3) | C15—Fe2—C22—C23 | 39.9 (4) |
C5—Fe1—C8—C7 | −48.1 (4) | C21—Fe2—C22—C23 | −119.8 (2) |
C1—Fe1—C8—C7 | −77.1 (2) | C19—Fe2—C22—C23 | −166.6 (2) |
C3—Fe1—C8—C7 | −159.65 (18) | C17—Fe2—C22—C23 | 117.19 (17) |
C10—Fe1—C8—C7 | 81.6 (2) | C18—Fe2—C22—C23 | 159.35 (16) |
C4—Fe1—C8—C7 | 170.5 (3) | C21—C22—C23—C24 | −0.1 (3) |
C7—C8—C9—C10 | −0.2 (3) | Fe2—C22—C23—C24 | 59.57 (18) |
Fe1—C8—C9—C10 | 59.47 (19) | C21—C22—C23—Fe2 | −59.65 (18) |
C7—C8—C9—Fe1 | −59.70 (18) | C16—Fe2—C23—C22 | −122.40 (17) |
C7—Fe1—C9—C8 | 38.04 (18) | C24—Fe2—C23—C22 | 118.7 (2) |
C2—Fe1—C9—C8 | −74.2 (2) | C20—Fe2—C23—C22 | 80.79 (19) |
C6—Fe1—C9—C8 | 82.5 (2) | C15—Fe2—C23—C22 | −164.31 (15) |
C5—Fe1—C9—C8 | 168.2 (3) | C21—Fe2—C23—C22 | 37.07 (17) |
C1—Fe1—C9—C8 | −39.8 (4) | C19—Fe2—C23—C22 | 165.3 (3) |
C3—Fe1—C9—C8 | −116.20 (18) | C17—Fe2—C23—C22 | −81.09 (19) |
C10—Fe1—C9—C8 | 120.1 (3) | C18—Fe2—C23—C22 | −49.9 (3) |
C4—Fe1—C9—C8 | −158.16 (17) | C16—Fe2—C23—C24 | 118.90 (18) |
C7—Fe1—C9—C10 | −82.0 (2) | C20—Fe2—C23—C24 | −37.90 (17) |
C8—Fe1—C9—C10 | −120.1 (3) | C22—Fe2—C23—C24 | −118.7 (2) |
C2—Fe1—C9—C10 | 165.73 (18) | C15—Fe2—C23—C24 | 77.0 (2) |
C6—Fe1—C9—C10 | −37.6 (2) | C21—Fe2—C23—C24 | −81.62 (19) |
C5—Fe1—C9—C10 | 48.1 (4) | C19—Fe2—C23—C24 | 46.6 (4) |
C1—Fe1—C9—C10 | −159.9 (3) | C17—Fe2—C23—C24 | 160.22 (17) |
C3—Fe1—C9—C10 | 123.72 (19) | C18—Fe2—C23—C24 | −168.6 (2) |
C4—Fe1—C9—C10 | 81.8 (2) | C22—C23—C24—C20 | 0.1 (3) |
C8—C9—C10—C6 | 0.2 (3) | Fe2—C23—C24—C20 | 59.82 (18) |
Fe1—C9—C10—C6 | 59.28 (19) | C22—C23—C24—Fe2 | −59.74 (18) |
C8—C9—C10—Fe1 | −59.13 (19) | C21—C20—C24—C23 | −0.1 (3) |
C7—C6—C10—C9 | 0.0 (3) | Fe2—C20—C24—C23 | −59.96 (18) |
Fe1—C6—C10—C9 | −59.4 (2) | C21—C20—C24—Fe2 | 59.90 (18) |
C7—C6—C10—Fe1 | 59.36 (18) | C16—Fe2—C24—C23 | −78.29 (19) |
C7—Fe1—C10—C9 | 80.8 (2) | C20—Fe2—C24—C23 | 118.9 (2) |
C8—Fe1—C10—C9 | 37.03 (18) | C22—Fe2—C24—C23 | 37.69 (17) |
C2—Fe1—C10—C9 | −36.8 (4) | C15—Fe2—C24—C23 | −121.07 (17) |
C6—Fe1—C10—C9 | 119.2 (3) | C21—Fe2—C24—C23 | 81.05 (18) |
C5—Fe1—C10—C9 | −160.68 (17) | C19—Fe2—C24—C23 | −162.73 (16) |
C1—Fe1—C10—C9 | 160.5 (3) | C17—Fe2—C24—C23 | −46.1 (3) |
C3—Fe1—C10—C9 | −75.3 (2) | C18—Fe2—C24—C23 | 166.0 (3) |
C4—Fe1—C10—C9 | −118.02 (18) | C16—Fe2—C24—C20 | 162.85 (15) |
C7—Fe1—C10—C6 | −38.41 (18) | C22—Fe2—C24—C20 | −81.16 (18) |
C8—Fe1—C10—C6 | −82.2 (2) | C15—Fe2—C24—C20 | 120.07 (16) |
C2—Fe1—C10—C6 | −156.1 (3) | C23—Fe2—C24—C20 | −118.9 (2) |
C9—Fe1—C10—C6 | −119.2 (3) | C21—Fe2—C24—C20 | −37.81 (16) |
C5—Fe1—C10—C6 | 80.1 (2) | C19—Fe2—C24—C20 | 78.41 (19) |
C1—Fe1—C10—C6 | 41.3 (4) | C17—Fe2—C24—C20 | −164.9 (2) |
C3—Fe1—C10—C6 | 165.43 (18) | C18—Fe2—C24—C20 | 47.2 (4) |
C4—Fe1—C10—C6 | 122.73 (19) | N4—N3—C25—C26 | −1.1 (3) |
N2—N1—C11—C12 | −0.9 (3) | N4—N3—C25—C15 | 178.98 (19) |
N2—N1—C11—C1 | 178.51 (19) | C16—C15—C25—N3 | 170.2 (2) |
C2—C1—C11—N1 | −170.4 (2) | C19—C15—C25—N3 | −13.2 (3) |
C5—C1—C11—N1 | 10.1 (3) | Fe2—C15—C25—N3 | −101.6 (2) |
Fe1—C1—C11—N1 | 99.8 (2) | C16—C15—C25—C26 | −9.7 (3) |
C2—C1—C11—C12 | 8.9 (4) | C19—C15—C25—C26 | 166.9 (2) |
C5—C1—C11—C12 | −170.5 (2) | Fe2—C15—C25—C26 | 78.5 (3) |
Fe1—C1—C11—C12 | −80.8 (3) | N3—C25—C26—C27 | 0.2 (3) |
N1—C11—C12—C13 | 1.1 (3) | C15—C25—C26—C27 | −179.9 (2) |
C1—C11—C12—C13 | −178.2 (2) | C25—C26—C27—C28 | 0.6 (3) |
C11—C12—C13—C14 | −0.3 (3) | N3—N4—C28—C27 | −0.3 (4) |
N1—N2—C14—C13 | 1.2 (4) | N3—N4—C28—Cl2 | −179.20 (16) |
N1—N2—C14—Cl1 | −178.37 (17) | C26—C27—C28—N4 | −0.6 (4) |
C12—C13—C14—N2 | −0.9 (4) | C26—C27—C28—Cl2 | 178.28 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N3i | 0.98 | 2.55 | 3.454 (4) | 153 |
C12—H12···N4i | 0.93 | 2.41 | 3.320 (4) | 166 |
C26—H26···N2ii | 0.93 | 2.43 | 3.302 (4) | 156 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N3i | 0.98 | 2.55 | 3.454 (4) | 153 |
C12—H12···N4i | 0.93 | 2.41 | 3.320 (4) | 166 |
C26—H26···N2ii | 0.93 | 2.43 | 3.302 (4) | 156 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, −y+1/2, −z+1. |
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Palladium catalyzed coupling reactions are widely used and powerful tools in organic synthesis (Meijere & Diederich, 2004). The organomercury compounds have a number of notable advantages over other organometallic compounds commonly used in cross-coupling reactions, including higher selectivity of reactions, extra stability, as well as easy availability by a direct mercuration of ferrocene (Beletskaya et al., 2001; Tsvetkov et al., 2000; Xu et al., 2010). The coupling reaction of with chloromercuriferrocene and 3,6-dichloropyridazine readily afforded the title compound.
There are two molecules in the asymmetric unit(Fig.1). The two cyclopentadienyl rings are almost parallel with dihedral angles of 2.16 (4)° and 2.71 (5)° for molecules containing Fe2 or Fe1, respectively. The dihedral angle between the pyridazinyl and substituted cyclopentadienyl ring is 9.65 (5)° and 11.53 (8)° for molecules containing Fe1 or Fe2, respectively. Intermolecular C—H···N hydrogen bonds construct a chain along the c axis direction (Fig.2).