supplementary materials


rn2116 scheme

Acta Cryst. (2014). E70, m2    [ doi:10.1107/S1600536813031310 ]

(6-Chloropyridazin-3-yl)ferrocene

G.-Q. Shi, W.-E. Zhao, X.-H. Zhao and L.-Y. Hao

Abstract top

The asymmetric unit of the title compound, [Fe(C5H5)(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.

Comment top

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).

Related literature top

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 top

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.

Refinement top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the molecules viewed down c axis.
(6-Chloropyridazin-3-yl)ferrocene top
Crystal data top
[Fe(C5H5)(C9H6ClN2)]F(000) = 2432
Mr = 298.55Dx = 1.611 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 20.5488 (19) ÅCell parameters from 5464 reflections
b = 12.3788 (6) Åθ = 3.1–26.3°
c = 23.043 (2) ŵ = 1.42 mm1
β = 122.843 (13)°T = 291 K
V = 4924.5 (7) Å3Block, brown
Z = 160.30 × 0.30 × 0.25 mm
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer
4575 independent reflections
Radiation source: Enhance (Mo) X-ray Source3783 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 16.2312 pixels mm-1θmax = 25.5°, θmin = 3.2°
ω scansh = 2324
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
k = 1414
Tmin = 0.675, Tmax = 0.718l = 2727
18413 measured reflections
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-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 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
[Fe(C5H5)(C9H6ClN2)]V = 4924.5 (7) Å3
Mr = 298.55Z = 16
Monoclinic, C2/cMo Kα radiation
a = 20.5488 (19) ŵ = 1.42 mm1
b = 12.3788 (6) ÅT = 291 K
c = 23.043 (2) Å0.30 × 0.30 × 0.25 mm
β = 122.843 (13)°
Data collection top
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 = 0.718Rint = 0.032
18413 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.078Δρmax = 0.36 e Å3
S = 1.04Δρmin = 0.23 e Å3
4575 reflectionsAbsolute structure: ?
325 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.542789 (17)0.30107 (3)0.582945 (16)0.03750 (11)
Fe20.203696 (17)0.43834 (2)0.410109 (15)0.03501 (10)
Cl10.65041 (5)0.24694 (6)0.71490 (4)0.0727 (2)
Cl20.11431 (5)0.99199 (6)0.30309 (4)0.0690 (2)
N10.52234 (11)0.00916 (17)0.60350 (11)0.0485 (5)
N20.54980 (12)0.09968 (17)0.64197 (12)0.0514 (5)
N30.23719 (10)0.74910 (16)0.41199 (10)0.0422 (5)
N40.21252 (11)0.84273 (16)0.37651 (11)0.0458 (5)
C10.53402 (12)0.14578 (19)0.54950 (12)0.0404 (5)
C20.56826 (14)0.2140 (2)0.52259 (12)0.0458 (6)
H20.61970.20500.53010.055*
C30.51425 (15)0.2960 (2)0.48304 (13)0.0528 (7)
H30.52220.35450.45890.063*
C40.44721 (14)0.2807 (2)0.48506 (13)0.0528 (7)
H40.40100.32670.46260.063*
C50.45863 (13)0.1893 (2)0.52575 (13)0.0456 (6)
H50.42170.16030.53620.055*
C60.5420 (2)0.3381 (3)0.66884 (17)0.0745 (10)
H60.50800.30670.68200.089*
C70.6158 (2)0.2982 (2)0.68728 (14)0.0697 (9)
H70.64170.23420.71550.084*
C80.64510 (15)0.3671 (2)0.65830 (14)0.0572 (7)
H80.69510.35970.66270.069*
C90.59049 (16)0.4488 (2)0.62266 (15)0.0577 (7)
H90.59550.50790.59710.069*
C100.52710 (17)0.4316 (2)0.62874 (16)0.0647 (8)
H100.48050.47650.60840.078*
C110.56917 (12)0.05099 (18)0.59310 (12)0.0383 (5)
C120.64703 (13)0.0226 (2)0.62229 (13)0.0440 (6)
H120.67930.06570.61530.053*
C130.67469 (14)0.0690 (2)0.66087 (13)0.0472 (6)
H130.72580.09110.68100.057*
C140.62236 (14)0.12723 (19)0.66835 (12)0.0442 (6)
C150.21916 (12)0.58613 (18)0.45514 (11)0.0361 (5)
C160.18188 (13)0.51278 (19)0.47649 (11)0.0399 (5)
H160.13080.52280.46950.048*
C170.23183 (13)0.4242 (2)0.50975 (12)0.0444 (6)
H170.22090.36150.52920.053*
C180.29996 (13)0.4399 (2)0.50910 (12)0.0453 (6)
H180.34400.39020.52790.054*
C190.29259 (12)0.53913 (19)0.47570 (11)0.0412 (5)
H190.33080.57020.46750.049*
C200.20433 (19)0.4178 (3)0.32253 (14)0.0656 (8)
H200.24040.45140.31260.079*
C210.21428 (17)0.3175 (2)0.35522 (14)0.0594 (7)
H210.25870.26900.37230.071*
C220.14951 (16)0.2994 (2)0.35885 (13)0.0562 (7)
H220.14100.23580.37930.067*
C230.09880 (15)0.3871 (2)0.32879 (13)0.0564 (7)
H230.04870.39530.32410.068*
C240.13262 (18)0.4609 (2)0.30618 (13)0.0621 (8)
H240.11020.52990.28290.074*
C250.18747 (12)0.68643 (17)0.41683 (11)0.0343 (5)
C260.10951 (13)0.71658 (19)0.38661 (12)0.0427 (6)
H260.07540.67230.39050.051*
C270.08504 (14)0.8115 (2)0.35173 (13)0.0470 (6)
H270.03420.83530.33120.056*
C280.14001 (14)0.87131 (19)0.34830 (12)0.0424 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.03557 (18)0.03842 (19)0.03580 (19)0.00429 (14)0.01758 (15)0.00388 (14)
Fe20.03542 (18)0.03567 (19)0.03032 (18)0.00343 (13)0.01547 (14)0.00137 (14)
Cl10.0749 (5)0.0669 (5)0.0773 (5)0.0009 (4)0.0419 (4)0.0199 (4)
Cl20.0785 (5)0.0568 (4)0.0694 (5)0.0043 (4)0.0386 (4)0.0203 (4)
N10.0378 (11)0.0504 (13)0.0625 (14)0.0083 (9)0.0306 (10)0.0079 (11)
N20.0472 (12)0.0534 (13)0.0617 (14)0.0125 (10)0.0348 (11)0.0065 (11)
N30.0360 (10)0.0450 (12)0.0488 (12)0.0090 (9)0.0251 (9)0.0034 (10)
N40.0474 (12)0.0457 (12)0.0513 (13)0.0103 (10)0.0312 (10)0.0015 (10)
C10.0343 (12)0.0448 (13)0.0409 (13)0.0060 (10)0.0195 (10)0.0123 (11)
C20.0416 (13)0.0578 (16)0.0394 (13)0.0023 (12)0.0230 (11)0.0063 (12)
C30.0499 (15)0.0681 (18)0.0377 (14)0.0025 (13)0.0219 (12)0.0024 (13)
C40.0393 (13)0.0653 (17)0.0389 (14)0.0044 (12)0.0116 (11)0.0041 (13)
C50.0331 (12)0.0510 (15)0.0468 (14)0.0087 (11)0.0179 (11)0.0134 (12)
C60.101 (3)0.080 (2)0.067 (2)0.046 (2)0.061 (2)0.0397 (18)
C70.099 (2)0.0494 (17)0.0309 (14)0.0075 (16)0.0161 (15)0.0060 (13)
C80.0437 (14)0.0570 (17)0.0541 (17)0.0112 (13)0.0154 (13)0.0136 (14)
C90.0603 (17)0.0383 (14)0.0687 (19)0.0101 (13)0.0312 (15)0.0052 (13)
C100.0603 (18)0.0564 (18)0.075 (2)0.0028 (14)0.0349 (16)0.0246 (16)
C110.0355 (12)0.0412 (13)0.0429 (13)0.0113 (10)0.0242 (10)0.0158 (11)
C120.0381 (12)0.0475 (14)0.0550 (15)0.0094 (11)0.0308 (12)0.0069 (12)
C130.0402 (13)0.0500 (15)0.0568 (16)0.0018 (11)0.0298 (12)0.0032 (12)
C140.0488 (14)0.0449 (14)0.0423 (14)0.0083 (11)0.0269 (12)0.0082 (11)
C150.0351 (12)0.0399 (12)0.0342 (12)0.0085 (10)0.0194 (10)0.0068 (10)
C160.0400 (12)0.0450 (13)0.0384 (13)0.0051 (10)0.0237 (11)0.0044 (11)
C170.0470 (14)0.0505 (15)0.0320 (12)0.0020 (11)0.0189 (11)0.0037 (11)
C180.0376 (12)0.0543 (15)0.0327 (12)0.0034 (11)0.0117 (10)0.0004 (11)
C190.0327 (12)0.0509 (14)0.0370 (13)0.0087 (10)0.0169 (10)0.0086 (11)
C200.084 (2)0.077 (2)0.0485 (16)0.0356 (18)0.0438 (16)0.0257 (15)
C210.0629 (18)0.0566 (17)0.0503 (16)0.0016 (14)0.0252 (14)0.0178 (14)
C220.0673 (18)0.0392 (14)0.0451 (15)0.0158 (13)0.0194 (14)0.0058 (12)
C230.0431 (14)0.0668 (18)0.0394 (14)0.0093 (13)0.0094 (11)0.0068 (13)
C240.086 (2)0.0470 (15)0.0294 (13)0.0004 (15)0.0158 (14)0.0025 (12)
C250.0355 (11)0.0377 (12)0.0346 (12)0.0112 (9)0.0221 (10)0.0112 (10)
C260.0373 (12)0.0453 (14)0.0527 (15)0.0080 (11)0.0291 (11)0.0032 (12)
C270.0376 (13)0.0530 (15)0.0528 (15)0.0003 (11)0.0260 (12)0.0006 (12)
C280.0508 (14)0.0411 (13)0.0380 (13)0.0037 (11)0.0259 (11)0.0019 (11)
Geometric parameters (Å, º) top
Fe1—C72.030 (3)C6—C71.423 (4)
Fe1—C82.036 (3)C6—H60.9800
Fe1—C22.039 (2)C7—C81.405 (4)
Fe1—C62.041 (3)C7—H70.9800
Fe1—C92.042 (3)C8—C91.398 (4)
Fe1—C52.042 (2)C8—H80.9800
Fe1—C12.042 (2)C9—C101.400 (4)
Fe1—C32.045 (3)C9—H90.9800
Fe1—C102.049 (3)C10—H100.9800
Fe1—C42.050 (2)C11—C121.403 (3)
Fe2—C162.033 (2)C12—C131.360 (3)
Fe2—C242.038 (3)C12—H120.9300
Fe2—C202.041 (3)C13—C141.381 (3)
Fe2—C222.041 (2)C13—H130.9300
Fe2—C152.041 (2)C15—C161.436 (3)
Fe2—C232.044 (2)C15—C191.437 (3)
Fe2—C212.045 (3)C15—C251.456 (3)
Fe2—C192.045 (2)C16—C171.411 (3)
Fe2—C172.049 (2)C16—H160.9800
Fe2—C182.055 (2)C17—C181.422 (3)
Cl1—C141.734 (3)C17—H170.9800
Cl2—C281.732 (2)C18—C191.413 (3)
N1—C111.337 (3)C18—H180.9800
N1—N21.348 (3)C19—H190.9800
N2—C141.314 (3)C20—C211.408 (4)
N3—C251.335 (3)C20—C241.413 (4)
N3—N41.349 (3)C20—H200.9800
N4—C281.310 (3)C21—C221.396 (4)
C1—C21.437 (3)C21—H210.9800
C1—C51.438 (3)C22—C231.400 (4)
C1—C111.456 (3)C22—H220.9800
C2—C31.413 (4)C23—C241.408 (4)
C2—H20.9800C23—H230.9800
C3—C41.416 (4)C24—H240.9800
C3—H30.9800C25—C261.407 (3)
C4—C51.405 (4)C26—C271.357 (3)
C4—H40.9800C26—H260.9300
C5—H50.9800C27—C281.388 (3)
C6—C101.407 (4)C27—H270.9300
C7—Fe1—C840.43 (12)C4—C5—Fe170.22 (14)
C7—Fe1—C2120.04 (12)C1—C5—Fe169.38 (12)
C8—Fe1—C2105.41 (11)C4—C5—H5125.9
C7—Fe1—C640.93 (13)C1—C5—H5125.9
C8—Fe1—C668.32 (12)Fe1—C5—H5125.9
C2—Fe1—C6156.98 (14)C10—C6—C7107.3 (3)
C7—Fe1—C967.54 (12)C10—C6—Fe170.17 (17)
C8—Fe1—C940.12 (11)C7—C6—Fe169.10 (16)
C2—Fe1—C9122.72 (11)C10—C6—H6126.3
C6—Fe1—C967.57 (12)C7—C6—H6126.3
C7—Fe1—C5125.15 (12)Fe1—C6—H6126.3
C8—Fe1—C5160.73 (11)C8—C7—C6108.1 (3)
C2—Fe1—C569.05 (10)C8—C7—Fe170.01 (15)
C6—Fe1—C5109.19 (11)C6—C7—Fe169.96 (17)
C9—Fe1—C5158.25 (11)C8—C7—H7126.0
C7—Fe1—C1106.73 (11)C6—C7—H7126.0
C8—Fe1—C1122.61 (10)Fe1—C7—H7126.0
C2—Fe1—C141.24 (9)C9—C8—C7107.7 (3)
C6—Fe1—C1122.15 (12)C9—C8—Fe170.17 (15)
C9—Fe1—C1159.18 (10)C7—C8—Fe169.55 (15)
C5—Fe1—C141.24 (9)C9—C8—H8126.2
C7—Fe1—C3155.42 (13)C7—C8—H8126.2
C8—Fe1—C3120.36 (12)Fe1—C8—H8126.2
C2—Fe1—C340.47 (10)C8—C9—C10109.0 (3)
C6—Fe1—C3161.87 (14)C8—C9—Fe169.71 (15)
C9—Fe1—C3107.86 (12)C10—C9—Fe170.26 (15)
C5—Fe1—C368.12 (11)C8—C9—H9125.5
C1—Fe1—C368.52 (10)C10—C9—H9125.5
C7—Fe1—C1067.98 (13)Fe1—C9—H9125.5
C8—Fe1—C1067.80 (11)C9—C10—C6108.0 (3)
C2—Fe1—C10159.77 (12)C9—C10—Fe169.72 (15)
C6—Fe1—C1040.25 (13)C6—C10—Fe169.58 (16)
C9—Fe1—C1040.03 (11)C9—C10—H10126.0
C5—Fe1—C10123.52 (11)C6—C10—H10126.0
C1—Fe1—C10158.49 (11)Fe1—C10—H10126.0
C3—Fe1—C10125.08 (12)N1—C11—C12121.3 (2)
C7—Fe1—C4162.27 (13)N1—C11—C1115.9 (2)
C8—Fe1—C4156.62 (12)C12—C11—C1122.9 (2)
C2—Fe1—C468.39 (10)C13—C12—C11119.1 (2)
C6—Fe1—C4125.99 (13)C13—C12—H12120.5
C9—Fe1—C4122.96 (11)C11—C12—H12120.5
C5—Fe1—C440.17 (10)C12—C13—C14116.0 (2)
C1—Fe1—C468.47 (10)C12—C13—H13122.0
C3—Fe1—C440.46 (10)C14—C13—H13122.0
C10—Fe1—C4109.84 (12)N2—C14—C13124.9 (2)
C16—Fe2—C24120.79 (11)N2—C14—Cl1114.90 (18)
C16—Fe2—C20157.30 (12)C13—C14—Cl1120.2 (2)
C24—Fe2—C2040.53 (12)C16—C15—C19106.9 (2)
C16—Fe2—C22122.93 (11)C16—C15—C25126.9 (2)
C24—Fe2—C2267.50 (11)C19—C15—C25126.12 (19)
C20—Fe2—C2267.47 (11)C16—C15—Fe269.06 (12)
C16—Fe2—C1541.28 (9)C19—C15—Fe269.57 (13)
C24—Fe2—C15106.80 (10)C25—C15—Fe2124.11 (15)
C20—Fe2—C15122.10 (11)C17—C16—C15108.2 (2)
C22—Fe2—C15159.23 (10)C17—C16—Fe270.37 (13)
C16—Fe2—C23106.09 (10)C15—C16—Fe269.67 (12)
C24—Fe2—C2340.36 (11)C17—C16—H16125.9
C20—Fe2—C2367.91 (12)C15—C16—H16125.9
C22—Fe2—C2340.09 (11)Fe2—C16—H16125.9
C15—Fe2—C23122.70 (10)C16—C17—C18108.5 (2)
C16—Fe2—C21159.65 (11)C16—C17—Fe269.19 (13)
C24—Fe2—C2167.82 (12)C18—C17—Fe269.96 (13)
C20—Fe2—C2140.32 (12)C16—C17—H17125.7
C22—Fe2—C2139.96 (11)C18—C17—H17125.7
C15—Fe2—C21158.49 (11)Fe2—C17—H17125.7
C23—Fe2—C2167.61 (12)C19—C18—C17108.0 (2)
C16—Fe2—C1968.93 (9)C19—C18—Fe269.48 (13)
C24—Fe2—C19124.63 (11)C17—C18—Fe269.50 (13)
C20—Fe2—C19108.94 (10)C19—C18—H18126.0
C22—Fe2—C19158.41 (11)C17—C18—H18126.0
C15—Fe2—C1941.17 (9)Fe2—C18—H18126.0
C23—Fe2—C19160.37 (11)C18—C19—C15108.3 (2)
C21—Fe2—C19123.45 (11)C18—C19—Fe270.20 (13)
C16—Fe2—C1740.45 (9)C15—C19—Fe269.26 (12)
C24—Fe2—C17156.29 (12)C18—C19—H19125.8
C20—Fe2—C17161.48 (12)C15—C19—H19125.8
C22—Fe2—C17108.07 (10)Fe2—C19—H19125.8
C15—Fe2—C1768.63 (9)C21—C20—C24107.7 (3)
C23—Fe2—C17121.13 (11)C21—C20—Fe270.00 (16)
C21—Fe2—C17124.78 (11)C24—C20—Fe269.61 (15)
C19—Fe2—C1768.16 (9)C21—C20—H20126.2
C16—Fe2—C1868.46 (9)C24—C20—H20126.2
C24—Fe2—C18161.48 (12)Fe2—C20—H20126.2
C20—Fe2—C18125.47 (12)C22—C21—C20107.9 (3)
C22—Fe2—C18123.02 (10)C22—C21—Fe269.87 (15)
C15—Fe2—C1868.69 (9)C20—C21—Fe269.68 (15)
C23—Fe2—C18157.24 (11)C22—C21—H21126.1
C21—Fe2—C18109.40 (11)C20—C21—H21126.1
C19—Fe2—C1840.33 (9)Fe2—C21—H21126.1
C17—Fe2—C1840.54 (9)C21—C22—C23108.9 (2)
C11—N1—N2119.70 (19)C21—C22—Fe270.17 (14)
C14—N2—N1119.0 (2)C23—C22—Fe270.07 (14)
C25—N3—N4119.79 (19)C21—C22—H22125.6
C28—N4—N3119.03 (18)C23—C22—H22125.6
C2—C1—C5107.1 (2)Fe2—C22—H22125.6
C2—C1—C11126.5 (2)C22—C23—C24107.6 (3)
C5—C1—C11126.4 (2)C22—C23—Fe269.84 (14)
C2—C1—Fe169.28 (13)C24—C23—Fe269.57 (15)
C5—C1—Fe169.38 (13)C22—C23—H23126.2
C11—C1—Fe1126.07 (16)C24—C23—H23126.2
C3—C2—C1107.7 (2)Fe2—C23—H23126.2
C3—C2—Fe169.98 (14)C23—C24—C20108.0 (3)
C1—C2—Fe169.49 (13)C23—C24—Fe270.07 (14)
C3—C2—H2126.2C20—C24—Fe269.86 (15)
C1—C2—H2126.2C23—C24—H24126.0
Fe1—C2—H2126.2C20—C24—H24126.0
C2—C3—C4108.7 (2)Fe2—C24—H24126.0
C2—C3—Fe169.55 (14)N3—C25—C26121.5 (2)
C4—C3—Fe169.96 (14)N3—C25—C15115.79 (19)
C2—C3—H3125.7C26—C25—C15122.74 (19)
C4—C3—H3125.7C27—C26—C25118.6 (2)
Fe1—C3—H3125.7C27—C26—H26120.7
C5—C4—C3108.4 (2)C25—C26—H26120.7
C5—C4—Fe169.61 (14)C26—C27—C28116.4 (2)
C3—C4—Fe169.57 (14)C26—C27—H27121.8
C5—C4—H4125.8C28—C27—H27121.8
C3—C4—H4125.8N4—C28—C27124.7 (2)
Fe1—C4—H4125.8N4—C28—Cl2115.15 (17)
C4—C5—C1108.1 (2)C27—C28—Cl2120.14 (19)
C11—N1—N2—C140.3 (3)C12—C13—C14—Cl1178.63 (18)
C25—N3—N4—C281.1 (3)C24—Fe2—C15—C16117.82 (16)
C7—Fe1—C1—C2116.75 (17)C20—Fe2—C15—C16159.42 (15)
C8—Fe1—C1—C275.44 (18)C22—Fe2—C15—C1647.2 (3)
C6—Fe1—C1—C2158.78 (17)C23—Fe2—C15—C1676.58 (17)
C9—Fe1—C1—C246.1 (4)C21—Fe2—C15—C16170.2 (3)
C5—Fe1—C1—C2118.6 (2)C19—Fe2—C15—C16118.36 (19)
C3—Fe1—C1—C237.70 (14)C17—Fe2—C15—C1637.53 (13)
C10—Fe1—C1—C2171.0 (3)C18—Fe2—C15—C1681.20 (14)
C4—Fe1—C1—C281.34 (15)C16—Fe2—C15—C19118.36 (19)
C7—Fe1—C1—C5124.68 (18)C24—Fe2—C15—C19123.82 (16)
C8—Fe1—C1—C5165.98 (16)C20—Fe2—C15—C1982.22 (18)
C2—Fe1—C1—C5118.6 (2)C22—Fe2—C15—C19165.5 (3)
C6—Fe1—C1—C582.64 (19)C23—Fe2—C15—C19165.06 (14)
C9—Fe1—C1—C5164.7 (3)C21—Fe2—C15—C1951.8 (3)
C3—Fe1—C1—C580.88 (16)C17—Fe2—C15—C1980.83 (14)
C10—Fe1—C1—C552.4 (4)C18—Fe2—C15—C1937.16 (13)
C4—Fe1—C1—C537.24 (15)C16—Fe2—C15—C25121.1 (2)
C7—Fe1—C1—C114.0 (2)C24—Fe2—C15—C253.3 (2)
C8—Fe1—C1—C1145.3 (2)C20—Fe2—C15—C2538.3 (2)
C2—Fe1—C1—C11120.8 (2)C22—Fe2—C15—C2574.0 (3)
C6—Fe1—C1—C1138.0 (2)C23—Fe2—C15—C2544.6 (2)
C9—Fe1—C1—C1174.7 (4)C21—Fe2—C15—C2568.7 (3)
C5—Fe1—C1—C11120.6 (3)C19—Fe2—C15—C25120.5 (2)
C3—Fe1—C1—C11158.5 (2)C17—Fe2—C15—C25158.7 (2)
C10—Fe1—C1—C1168.2 (4)C18—Fe2—C15—C25157.7 (2)
C4—Fe1—C1—C11157.9 (2)C19—C15—C16—C170.6 (2)
C5—C1—C2—C30.5 (3)C25—C15—C16—C17177.7 (2)
C11—C1—C2—C3180.0 (2)Fe2—C15—C16—C1760.09 (16)
Fe1—C1—C2—C359.82 (17)C19—C15—C16—Fe259.53 (15)
C5—C1—C2—Fe159.31 (15)C25—C15—C16—Fe2117.6 (2)
C11—C1—C2—Fe1120.2 (2)C24—Fe2—C16—C17160.71 (15)
C7—Fe1—C2—C3160.17 (16)C20—Fe2—C16—C17169.5 (2)
C8—Fe1—C2—C3118.99 (17)C22—Fe2—C16—C1779.03 (17)
C6—Fe1—C2—C3170.4 (3)C15—Fe2—C16—C17119.01 (19)
C9—Fe1—C2—C378.97 (18)C23—Fe2—C16—C17119.41 (15)
C5—Fe1—C2—C380.45 (16)C21—Fe2—C16—C1750.7 (3)
C1—Fe1—C2—C3118.8 (2)C19—Fe2—C16—C1780.64 (15)
C10—Fe1—C2—C351.7 (4)C18—Fe2—C16—C1737.22 (14)
C4—Fe1—C2—C337.20 (16)C24—Fe2—C16—C1580.28 (16)
C7—Fe1—C2—C181.07 (17)C20—Fe2—C16—C1550.5 (3)
C8—Fe1—C2—C1122.25 (15)C22—Fe2—C16—C15161.95 (13)
C6—Fe1—C2—C151.6 (3)C23—Fe2—C16—C15121.58 (14)
C9—Fe1—C2—C1162.27 (14)C21—Fe2—C16—C15169.7 (3)
C5—Fe1—C2—C138.31 (14)C19—Fe2—C16—C1538.37 (13)
C3—Fe1—C2—C1118.8 (2)C17—Fe2—C16—C15119.01 (19)
C10—Fe1—C2—C1170.4 (3)C18—Fe2—C16—C1581.80 (14)
C4—Fe1—C2—C181.56 (15)C15—C16—C17—C180.6 (3)
C1—C2—C3—C40.3 (3)Fe2—C16—C17—C1859.06 (16)
Fe1—C2—C3—C459.20 (18)C15—C16—C17—Fe259.65 (15)
C1—C2—C3—Fe159.51 (16)C24—Fe2—C17—C1644.9 (3)
C7—Fe1—C3—C244.9 (3)C20—Fe2—C17—C16167.2 (3)
C8—Fe1—C3—C277.75 (18)C22—Fe2—C17—C16119.92 (15)
C6—Fe1—C3—C2167.9 (3)C15—Fe2—C17—C1638.28 (13)
C9—Fe1—C3—C2119.82 (16)C23—Fe2—C17—C1677.91 (17)
C5—Fe1—C3—C282.93 (16)C21—Fe2—C17—C16160.88 (15)
C1—Fe1—C3—C238.39 (14)C19—Fe2—C17—C1682.71 (15)
C10—Fe1—C3—C2160.64 (15)C18—Fe2—C17—C16120.1 (2)
C4—Fe1—C3—C2120.0 (2)C16—Fe2—C17—C18120.1 (2)
C7—Fe1—C3—C4164.9 (3)C24—Fe2—C17—C18164.9 (2)
C8—Fe1—C3—C4162.27 (16)C20—Fe2—C17—C1847.2 (4)
C2—Fe1—C3—C4120.0 (2)C22—Fe2—C17—C18120.03 (16)
C6—Fe1—C3—C447.9 (4)C15—Fe2—C17—C1881.78 (15)
C9—Fe1—C3—C4120.20 (17)C23—Fe2—C17—C18162.03 (15)
C5—Fe1—C3—C437.05 (15)C21—Fe2—C17—C1879.06 (18)
C1—Fe1—C3—C481.59 (16)C19—Fe2—C17—C1837.34 (14)
C10—Fe1—C3—C479.38 (19)C16—C17—C18—C190.4 (3)
C2—C3—C4—C50.0 (3)Fe2—C17—C18—C1958.98 (16)
Fe1—C3—C4—C558.93 (17)C16—C17—C18—Fe258.58 (16)
C2—C3—C4—Fe158.95 (18)C16—Fe2—C18—C1982.41 (15)
C7—Fe1—C4—C539.2 (4)C24—Fe2—C18—C1941.3 (4)
C8—Fe1—C4—C5161.4 (2)C20—Fe2—C18—C1977.08 (18)
C2—Fe1—C4—C582.70 (16)C22—Fe2—C18—C19161.46 (15)
C6—Fe1—C4—C576.7 (2)C15—Fe2—C18—C1937.91 (13)
C9—Fe1—C4—C5161.44 (15)C23—Fe2—C18—C19162.6 (3)
C1—Fe1—C4—C538.20 (14)C21—Fe2—C18—C19119.22 (15)
C3—Fe1—C4—C5119.9 (2)C17—Fe2—C18—C19119.5 (2)
C10—Fe1—C4—C5118.86 (16)C16—Fe2—C18—C1737.13 (14)
C7—Fe1—C4—C3159.2 (4)C24—Fe2—C18—C17160.8 (3)
C8—Fe1—C4—C341.5 (3)C20—Fe2—C18—C17163.38 (16)
C2—Fe1—C4—C337.21 (16)C22—Fe2—C18—C1779.00 (18)
C6—Fe1—C4—C3163.43 (18)C15—Fe2—C18—C1781.63 (15)
C9—Fe1—C4—C378.64 (19)C23—Fe2—C18—C1743.0 (3)
C5—Fe1—C4—C3119.9 (2)C21—Fe2—C18—C17121.24 (16)
C1—Fe1—C4—C381.71 (16)C19—Fe2—C18—C17119.5 (2)
C10—Fe1—C4—C3121.23 (17)C17—C18—C19—C150.0 (3)
C3—C4—C5—C10.3 (3)Fe2—C18—C19—C1558.95 (15)
Fe1—C4—C5—C159.24 (16)C17—C18—C19—Fe258.99 (16)
C3—C4—C5—Fe158.90 (18)C16—C15—C19—C180.3 (2)
C2—C1—C5—C40.5 (3)C25—C15—C19—C18177.5 (2)
C11—C1—C5—C4180.0 (2)Fe2—C15—C19—C1859.52 (16)
Fe1—C1—C5—C459.77 (17)C16—C15—C19—Fe259.20 (15)
C2—C1—C5—Fe159.25 (16)C25—C15—C19—Fe2118.0 (2)
C11—C1—C5—Fe1120.3 (2)C16—Fe2—C19—C1881.13 (15)
C7—Fe1—C5—C4166.37 (17)C24—Fe2—C19—C18165.25 (16)
C8—Fe1—C5—C4157.4 (3)C20—Fe2—C19—C18122.94 (16)
C2—Fe1—C5—C480.92 (16)C22—Fe2—C19—C1846.5 (3)
C6—Fe1—C5—C4123.53 (18)C15—Fe2—C19—C18119.60 (19)
C9—Fe1—C5—C446.1 (4)C23—Fe2—C19—C18159.8 (3)
C1—Fe1—C5—C4119.2 (2)C21—Fe2—C19—C1880.62 (18)
C3—Fe1—C5—C437.31 (15)C17—Fe2—C19—C1837.53 (14)
C10—Fe1—C5—C481.17 (19)C16—Fe2—C19—C1538.47 (13)
C7—Fe1—C5—C174.4 (2)C24—Fe2—C19—C1575.15 (18)
C8—Fe1—C5—C138.2 (4)C20—Fe2—C19—C15117.46 (16)
C2—Fe1—C5—C138.31 (14)C22—Fe2—C19—C15166.1 (3)
C6—Fe1—C5—C1117.24 (18)C23—Fe2—C19—C1540.2 (4)
C9—Fe1—C5—C1165.3 (3)C21—Fe2—C19—C15159.78 (15)
C3—Fe1—C5—C181.92 (15)C17—Fe2—C19—C1582.07 (14)
C10—Fe1—C5—C1159.60 (16)C18—Fe2—C19—C15119.60 (19)
C4—Fe1—C5—C1119.2 (2)C16—Fe2—C20—C21159.7 (2)
C7—Fe1—C6—C10118.5 (2)C24—Fe2—C20—C21118.7 (2)
C8—Fe1—C6—C1080.81 (18)C22—Fe2—C20—C2137.46 (17)
C2—Fe1—C6—C10159.0 (2)C15—Fe2—C20—C21163.35 (16)
C9—Fe1—C6—C1037.38 (17)C23—Fe2—C20—C2180.95 (18)
C5—Fe1—C6—C10119.59 (18)C19—Fe2—C20—C21119.75 (17)
C1—Fe1—C6—C10163.40 (16)C17—Fe2—C20—C2142.1 (4)
C3—Fe1—C6—C1041.4 (4)C18—Fe2—C20—C2177.9 (2)
C4—Fe1—C6—C1077.9 (2)C16—Fe2—C20—C2441.0 (3)
C8—Fe1—C6—C737.65 (17)C22—Fe2—C20—C2481.23 (18)
C2—Fe1—C6—C740.5 (3)C15—Fe2—C20—C2477.96 (18)
C9—Fe1—C6—C781.08 (18)C23—Fe2—C20—C2437.74 (16)
C5—Fe1—C6—C7121.94 (17)C21—Fe2—C20—C24118.7 (2)
C1—Fe1—C6—C778.14 (19)C19—Fe2—C20—C24121.55 (16)
C3—Fe1—C6—C7159.9 (3)C17—Fe2—C20—C24160.8 (3)
C10—Fe1—C6—C7118.5 (2)C18—Fe2—C20—C24163.38 (16)
C4—Fe1—C6—C7163.59 (17)C24—C20—C21—C220.0 (3)
C10—C6—C7—C80.1 (3)Fe2—C20—C21—C2259.66 (18)
Fe1—C6—C7—C859.90 (19)C24—C20—C21—Fe259.65 (18)
C10—C6—C7—Fe160.03 (19)C16—Fe2—C21—C2238.4 (4)
C2—Fe1—C7—C878.14 (19)C24—Fe2—C21—C2280.97 (18)
C6—Fe1—C7—C8118.9 (2)C20—Fe2—C21—C22119.0 (2)
C9—Fe1—C7—C837.75 (17)C15—Fe2—C21—C22160.4 (2)
C5—Fe1—C7—C8162.51 (16)C23—Fe2—C21—C2237.19 (16)
C1—Fe1—C7—C8120.98 (17)C19—Fe2—C21—C22161.23 (15)
C3—Fe1—C7—C846.2 (3)C17—Fe2—C21—C2276.05 (19)
C10—Fe1—C7—C881.15 (18)C18—Fe2—C21—C22118.63 (17)
C4—Fe1—C7—C8167.6 (3)C16—Fe2—C21—C20157.4 (3)
C8—Fe1—C7—C6118.9 (2)C24—Fe2—C21—C2038.00 (17)
C2—Fe1—C7—C6162.93 (17)C22—Fe2—C21—C20119.0 (2)
C9—Fe1—C7—C681.18 (19)C15—Fe2—C21—C2041.4 (4)
C5—Fe1—C7—C678.6 (2)C23—Fe2—C21—C2081.78 (19)
C1—Fe1—C7—C6120.09 (17)C19—Fe2—C21—C2079.8 (2)
C3—Fe1—C7—C6165.1 (3)C17—Fe2—C21—C20164.97 (16)
C10—Fe1—C7—C637.78 (17)C18—Fe2—C21—C20122.40 (18)
C4—Fe1—C7—C648.6 (4)C20—C21—C22—C230.0 (3)
C6—C7—C8—C90.2 (3)Fe2—C21—C22—C2359.58 (18)
Fe1—C7—C8—C960.09 (19)C20—C21—C22—Fe259.54 (18)
C6—C7—C8—Fe159.86 (19)C16—Fe2—C22—C21165.08 (16)
C7—Fe1—C8—C9118.6 (3)C24—Fe2—C22—C2181.84 (19)
C2—Fe1—C8—C9122.90 (18)C20—Fe2—C22—C2137.80 (18)
C6—Fe1—C8—C980.5 (2)C15—Fe2—C22—C21159.7 (3)
C5—Fe1—C8—C9166.7 (3)C23—Fe2—C22—C21119.8 (2)
C1—Fe1—C8—C9164.34 (16)C19—Fe2—C22—C2146.9 (3)
C3—Fe1—C8—C981.8 (2)C17—Fe2—C22—C21123.02 (17)
C10—Fe1—C8—C936.95 (18)C18—Fe2—C22—C2180.87 (19)
C4—Fe1—C8—C951.9 (3)C16—Fe2—C22—C2375.13 (19)
C2—Fe1—C8—C7118.51 (19)C24—Fe2—C22—C2337.94 (17)
C6—Fe1—C8—C738.10 (19)C20—Fe2—C22—C2381.99 (19)
C9—Fe1—C8—C7118.6 (3)C15—Fe2—C22—C2339.9 (4)
C5—Fe1—C8—C748.1 (4)C21—Fe2—C22—C23119.8 (2)
C1—Fe1—C8—C777.1 (2)C19—Fe2—C22—C23166.6 (2)
C3—Fe1—C8—C7159.65 (18)C17—Fe2—C22—C23117.19 (17)
C10—Fe1—C8—C781.6 (2)C18—Fe2—C22—C23159.35 (16)
C4—Fe1—C8—C7170.5 (3)C21—C22—C23—C240.1 (3)
C7—C8—C9—C100.2 (3)Fe2—C22—C23—C2459.57 (18)
Fe1—C8—C9—C1059.47 (19)C21—C22—C23—Fe259.65 (18)
C7—C8—C9—Fe159.70 (18)C16—Fe2—C23—C22122.40 (17)
C7—Fe1—C9—C838.04 (18)C24—Fe2—C23—C22118.7 (2)
C2—Fe1—C9—C874.2 (2)C20—Fe2—C23—C2280.79 (19)
C6—Fe1—C9—C882.5 (2)C15—Fe2—C23—C22164.31 (15)
C5—Fe1—C9—C8168.2 (3)C21—Fe2—C23—C2237.07 (17)
C1—Fe1—C9—C839.8 (4)C19—Fe2—C23—C22165.3 (3)
C3—Fe1—C9—C8116.20 (18)C17—Fe2—C23—C2281.09 (19)
C10—Fe1—C9—C8120.1 (3)C18—Fe2—C23—C2249.9 (3)
C4—Fe1—C9—C8158.16 (17)C16—Fe2—C23—C24118.90 (18)
C7—Fe1—C9—C1082.0 (2)C20—Fe2—C23—C2437.90 (17)
C8—Fe1—C9—C10120.1 (3)C22—Fe2—C23—C24118.7 (2)
C2—Fe1—C9—C10165.73 (18)C15—Fe2—C23—C2477.0 (2)
C6—Fe1—C9—C1037.6 (2)C21—Fe2—C23—C2481.62 (19)
C5—Fe1—C9—C1048.1 (4)C19—Fe2—C23—C2446.6 (4)
C1—Fe1—C9—C10159.9 (3)C17—Fe2—C23—C24160.22 (17)
C3—Fe1—C9—C10123.72 (19)C18—Fe2—C23—C24168.6 (2)
C4—Fe1—C9—C1081.8 (2)C22—C23—C24—C200.1 (3)
C8—C9—C10—C60.2 (3)Fe2—C23—C24—C2059.82 (18)
Fe1—C9—C10—C659.28 (19)C22—C23—C24—Fe259.74 (18)
C8—C9—C10—Fe159.13 (19)C21—C20—C24—C230.1 (3)
C7—C6—C10—C90.0 (3)Fe2—C20—C24—C2359.96 (18)
Fe1—C6—C10—C959.4 (2)C21—C20—C24—Fe259.90 (18)
C7—C6—C10—Fe159.36 (18)C16—Fe2—C24—C2378.29 (19)
C7—Fe1—C10—C980.8 (2)C20—Fe2—C24—C23118.9 (2)
C8—Fe1—C10—C937.03 (18)C22—Fe2—C24—C2337.69 (17)
C2—Fe1—C10—C936.8 (4)C15—Fe2—C24—C23121.07 (17)
C6—Fe1—C10—C9119.2 (3)C21—Fe2—C24—C2381.05 (18)
C5—Fe1—C10—C9160.68 (17)C19—Fe2—C24—C23162.73 (16)
C1—Fe1—C10—C9160.5 (3)C17—Fe2—C24—C2346.1 (3)
C3—Fe1—C10—C975.3 (2)C18—Fe2—C24—C23166.0 (3)
C4—Fe1—C10—C9118.02 (18)C16—Fe2—C24—C20162.85 (15)
C7—Fe1—C10—C638.41 (18)C22—Fe2—C24—C2081.16 (18)
C8—Fe1—C10—C682.2 (2)C15—Fe2—C24—C20120.07 (16)
C2—Fe1—C10—C6156.1 (3)C23—Fe2—C24—C20118.9 (2)
C9—Fe1—C10—C6119.2 (3)C21—Fe2—C24—C2037.81 (16)
C5—Fe1—C10—C680.1 (2)C19—Fe2—C24—C2078.41 (19)
C1—Fe1—C10—C641.3 (4)C17—Fe2—C24—C20164.9 (2)
C3—Fe1—C10—C6165.43 (18)C18—Fe2—C24—C2047.2 (4)
C4—Fe1—C10—C6122.73 (19)N4—N3—C25—C261.1 (3)
N2—N1—C11—C120.9 (3)N4—N3—C25—C15178.98 (19)
N2—N1—C11—C1178.51 (19)C16—C15—C25—N3170.2 (2)
C2—C1—C11—N1170.4 (2)C19—C15—C25—N313.2 (3)
C5—C1—C11—N110.1 (3)Fe2—C15—C25—N3101.6 (2)
Fe1—C1—C11—N199.8 (2)C16—C15—C25—C269.7 (3)
C2—C1—C11—C128.9 (4)C19—C15—C25—C26166.9 (2)
C5—C1—C11—C12170.5 (2)Fe2—C15—C25—C2678.5 (3)
Fe1—C1—C11—C1280.8 (3)N3—C25—C26—C270.2 (3)
N1—C11—C12—C131.1 (3)C15—C25—C26—C27179.9 (2)
C1—C11—C12—C13178.2 (2)C25—C26—C27—C280.6 (3)
C11—C12—C13—C140.3 (3)N3—N4—C28—C270.3 (4)
N1—N2—C14—C131.2 (4)N3—N4—C28—Cl2179.20 (16)
N1—N2—C14—Cl1178.37 (17)C26—C27—C28—N40.6 (4)
C12—C13—C14—N20.9 (4)C26—C27—C28—Cl2178.28 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N3i0.982.553.454 (4)153
C12—H12···N4i0.932.413.320 (4)166
C26—H26···N2ii0.932.433.302 (4)156
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N3i0.982.553.454 (4)153
C12—H12···N4i0.932.413.320 (4)166
C26—H26···N2ii0.932.433.302 (4)156
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y+1/2, z+1.
references
References top

Agilent (2011). CrysAlis PRO. Agilent Technologies, Abingdon, England.

Beletskaya, I. P., Tsvetkov, A. V., Latyshev, G. V., Tafeenko, V. A. & Lukashev, N. V. (2001). J. Organomet. Chem. 637–639, 653–663.

Meijere, A. D. & Diederich, F. (2004). Metal-catalyzed Cross-coupling Reactions. 2nd ed. Weinheim: Wiley-VCH.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tsvetkov, A. V., Tsvetkov, A. V., Lukashev, N. V. & Beletskaya, I. P. (2000). Tetrahedron Lett. 41, 3987–3990.

Xu, C., Li, H. M., Wang, Z. Q., Fu, W. J., Zhang, Y. Q. & Ji, B. M. (2012). Aust. J. Chem. 65, 366–370.

Xu, C., Zhang, Y. P., Wang, Z. Q., Fu, W. J., Hao, X. Q., Xu, Y. & Ji, B. M. (2010). Chem. Commun. 46, 6852–6854.