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The title ferrocenyl imidazolium salt, [Fe(C5H5)(C16H16N2)]I, results from the reaction of 1-benzyl­imidazole and (ferrocenyl­methyl)­tri­methyl­ammonium iodide in aceto­nitrile. It crystallizes in a monoclinic space group, showing disorder of a cyclo­penta­dienyl ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011006/cv6308sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011006/cv63083sup2.hkl
Contains datablock 3

CCDC reference: 242037

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.029
  • wR factor = 0.068
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.71 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 3 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.32 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C17 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C20 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C21 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C20' PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C21' PLAT301_ALERT_3_C Main Residue Disorder ......................... 17.00 Perc. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 72 C21'-FE -C13 -C14 -164.00 6.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 82 C21'-FE -C13 -C12 -44.00 6.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 88 C17'-FE -C14 -C13 -21.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 98 C17'-FE -C14 -C15 -139.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 146 C19'-FE -C16 -C15 -49.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 156 C19'-FE -C16 -C12 -168.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 283 C14 -FE -C17'-C21' -167.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 293 C14 -FE -C17'-C18' -50.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 333 C16 -FE -C19'-C18' -142.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 344 C16 -FE -C19'-C20' -25.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 350 C12 -FE -C20'-C19' -119.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 361 C12 -FE -C20'-C21' 2.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 383 C13 -FE -C21'-C20' -142.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 393 C13 -FE -C21'-C17' -23.00 7.00 1.555 1.555 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.93(3), Rep 0.930(10) ...... 3.00 su-Rat C9 -H9 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.94(3), Rep 0.935(10) ...... 3.00 su-Rat C10 -H10 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.710 Tmax scaled 0.600 Tmin scaled 0.516
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 27 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 17 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-Benzyl-3-(ferrocenylmethyl)imidazolium iodide top
Crystal data top
[Fe(C5H5)(C16H16N2)]IF(000) = 960
Mr = 484.15Dx = 1.622 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.086 (2) ÅCell parameters from 34 reflections
b = 11.043 (2) Åθ = 2.8–14.8°
c = 13.729 (2) ŵ = 2.32 mm1
β = 92.11 (2)°T = 292 K
V = 1982.5 (5) Å3Block, orange
Z = 40.30 × 0.22 × 0.22 mm
Data collection top
Siemens P4
diffractometer
2818 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.3°, θmin = 2.1°
ω scansh = 015
Absorption correction: multi-scan
(SHELXTL; Siemens, 1994)
k = 013
Tmin = 0.727, Tmax = 0.845l = 1616
4120 measured reflections3 standard reflections every 97 reflections
3593 independent reflections intensity decay: 3.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0392P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
3593 reflectionsΔρmax = 0.44 e Å3
266 parametersΔρmin = 0.47 e Å3
17 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0032 (2)
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*/UeqOcc. (<1)
I0.754301 (18)0.22798 (2)0.456232 (18)0.05089 (11)
Fe0.41642 (3)0.01771 (4)0.19240 (3)0.03604 (13)
N10.5968 (2)0.4982 (2)0.2582 (2)0.0427 (7)
N20.4761 (2)0.3693 (2)0.2315 (2)0.0429 (7)
C10.7397 (3)0.7543 (3)0.3763 (3)0.0469 (9)
H10.80210.74480.34700.056*
C20.7231 (3)0.8543 (3)0.4325 (3)0.0569 (10)
H20.77440.91190.44150.068*
C30.6314 (3)0.8696 (4)0.4754 (3)0.0629 (11)
H30.62030.93830.51270.075*
C40.5560 (3)0.7848 (4)0.4638 (3)0.0659 (11)
H40.49380.79540.49350.079*
C50.5725 (3)0.6833 (3)0.4078 (3)0.0535 (9)
H50.52130.62520.40040.064*
C60.6643 (2)0.6671 (3)0.3627 (2)0.0412 (8)
C70.6881 (3)0.5564 (3)0.3026 (3)0.0507 (9)
H7A0.73330.57980.25140.061*
H7B0.72420.49810.34400.061*
C80.5564 (3)0.3963 (3)0.2885 (3)0.0448 (9)
C90.4658 (3)0.4576 (4)0.1619 (3)0.0545 (10)
C100.5402 (3)0.5385 (4)0.1788 (3)0.0553 (10)
C110.4134 (3)0.2582 (3)0.2378 (3)0.0511 (9)
H11A0.35500.26400.19240.061*
H11B0.38800.25070.30300.061*
C120.4746 (2)0.1491 (3)0.2146 (2)0.0362 (7)
C130.5220 (2)0.0659 (3)0.2806 (2)0.0416 (8)
H130.52210.07130.34820.050*
C140.5687 (2)0.0254 (3)0.2278 (3)0.0421 (8)
H140.60320.09230.25390.051*
C150.5541 (2)0.0019 (3)0.1278 (3)0.0480 (9)
H150.57840.04330.07640.058*
C160.4961 (2)0.1097 (3)0.1191 (2)0.0426 (8)
H160.47580.14790.06120.051*
C170.2653 (10)0.0114 (9)0.2161 (10)0.073 (3)0.67
H170.22930.05670.23500.087*0.67
C180.3137 (7)0.0968 (9)0.2789 (4)0.0473 (16)0.67
H180.31600.09480.34660.057*0.67
C190.3577 (6)0.1853 (6)0.2202 (7)0.0504 (19)0.67
H190.39250.25360.24300.060*0.67
C200.3409 (10)0.1545 (10)0.1217 (5)0.073 (3)0.67
H200.36440.19650.06820.088*0.67
C210.2816 (14)0.0480 (15)0.1193 (7)0.078 (4)0.67
H210.25720.00840.06330.093*0.67
C17'0.2631 (18)0.0033 (14)0.1770 (14)0.043 (5)0.33
H17'0.23190.07750.16410.052*0.33
C18'0.2863 (15)0.0461 (19)0.2701 (8)0.0473 (16)0.33
H18'0.26920.01290.32960.057*0.33
C19'0.3398 (14)0.1543 (16)0.2563 (15)0.0504 (19)0.33
H19'0.37020.20120.30560.060*0.33
C20'0.340 (2)0.1808 (16)0.1563 (17)0.073 (3)0.33
H20'0.36470.25100.12800.088*0.33
C21'0.296 (4)0.080 (3)0.1070 (9)0.068 (8)0.33
H21'0.28990.07100.03970.081*0.33
H80.583 (2)0.351 (3)0.343 (2)0.028 (8)*
H90.417 (2)0.447 (3)0.112 (2)0.073 (13)*
H100.559 (3)0.609 (2)0.145 (3)0.092 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.04974 (16)0.04731 (16)0.05534 (17)0.00458 (11)0.00190 (11)0.00035 (12)
Fe0.0305 (2)0.0360 (3)0.0414 (3)0.0057 (2)0.0013 (2)0.0010 (2)
N10.0350 (15)0.0335 (16)0.0597 (19)0.0004 (12)0.0024 (13)0.0044 (13)
N20.0362 (15)0.0326 (15)0.0598 (19)0.0027 (12)0.0006 (14)0.0026 (14)
C10.045 (2)0.042 (2)0.054 (2)0.0035 (16)0.0031 (17)0.0086 (16)
C20.065 (3)0.046 (2)0.059 (3)0.0132 (19)0.012 (2)0.0005 (19)
C30.088 (3)0.053 (2)0.048 (2)0.002 (2)0.006 (2)0.0126 (19)
C40.064 (3)0.078 (3)0.057 (3)0.001 (2)0.014 (2)0.011 (2)
C50.046 (2)0.055 (2)0.059 (2)0.0078 (18)0.0041 (18)0.003 (2)
C60.0398 (19)0.0377 (19)0.045 (2)0.0002 (15)0.0068 (16)0.0033 (16)
C70.0331 (18)0.045 (2)0.074 (3)0.0017 (16)0.0034 (17)0.0008 (19)
C80.040 (2)0.0309 (19)0.063 (2)0.0056 (15)0.0022 (18)0.0022 (17)
C90.046 (2)0.058 (3)0.059 (3)0.0023 (19)0.0083 (19)0.002 (2)
C100.051 (2)0.054 (2)0.061 (2)0.002 (2)0.002 (2)0.016 (2)
C110.0402 (19)0.035 (2)0.079 (3)0.0056 (15)0.0057 (18)0.0028 (17)
C120.0294 (16)0.0350 (18)0.044 (2)0.0054 (14)0.0006 (14)0.0044 (15)
C130.0385 (18)0.048 (2)0.0379 (18)0.0070 (16)0.0053 (15)0.0052 (16)
C140.0277 (16)0.0406 (19)0.058 (2)0.0024 (15)0.0076 (15)0.0022 (17)
C150.0393 (19)0.052 (2)0.053 (2)0.0071 (17)0.0114 (17)0.0169 (18)
C160.0404 (19)0.049 (2)0.0389 (19)0.0127 (16)0.0051 (15)0.0039 (16)
C170.036 (5)0.052 (5)0.132 (10)0.004 (3)0.030 (8)0.029 (7)
C180.050 (5)0.037 (5)0.057 (3)0.014 (3)0.014 (3)0.005 (4)
C190.048 (4)0.026 (3)0.077 (6)0.011 (3)0.004 (4)0.008 (3)
C200.079 (4)0.060 (5)0.082 (7)0.039 (5)0.014 (6)0.019 (5)
C210.053 (10)0.110 (12)0.066 (8)0.044 (8)0.034 (9)0.028 (8)
C17'0.032 (8)0.044 (9)0.052 (10)0.017 (7)0.013 (11)0.021 (9)
C18'0.050 (5)0.037 (5)0.057 (3)0.014 (3)0.014 (3)0.005 (4)
C19'0.048 (4)0.026 (3)0.077 (6)0.011 (3)0.004 (4)0.008 (3)
C20'0.079 (4)0.060 (5)0.082 (7)0.039 (5)0.014 (6)0.019 (5)
C21'0.048 (13)0.079 (17)0.076 (15)0.024 (11)0.000 (11)0.040 (13)
Geometric parameters (Å, º) top
Fe—C122.012 (3)C9—H90.930 (10)
Fe—C172.017 (12)C10—H100.935 (10)
Fe—C17'2.02 (2)C11—C121.487 (4)
Fe—C182.024 (6)C11—H11A0.9700
Fe—C212.026 (17)C11—H11B0.9700
Fe—C132.027 (3)C12—C131.418 (4)
Fe—C19'2.029 (17)C12—C161.420 (4)
Fe—C202.033 (11)C13—C141.396 (4)
Fe—C142.036 (3)C13—H130.9300
Fe—C162.039 (3)C14—C151.412 (5)
Fe—C192.045 (7)C14—H140.9300
Fe—C21'2.05 (4)C15—C161.414 (5)
Fe—C152.048 (3)C15—H150.9300
N1—C81.317 (4)C16—H160.9300
N1—C101.369 (4)C17—C211.412 (4)
N1—C71.469 (4)C17—C181.412 (4)
N2—C81.321 (4)C17—H170.9300
N2—C91.370 (5)C18—C191.403 (4)
N2—C111.480 (4)C18—H180.9300
C1—C21.369 (5)C19—C201.404 (4)
C1—C61.386 (5)C19—H190.9300
C1—H10.9300C20—C211.409 (4)
C2—C31.366 (5)C20—H200.9300
C2—H20.9300C21—H210.9300
C3—C41.366 (6)C17'—C21'1.413 (5)
C3—H30.9300C17'—C18'1.413 (5)
C4—C51.380 (5)C17'—H17'0.9300
C4—H40.9300C18'—C19'1.402 (5)
C5—C61.384 (5)C18'—H18'0.9300
C5—H50.9300C19'—C20'1.404 (5)
C6—C71.513 (5)C19'—H19'0.9300
C7—H7A0.9700C20'—C21'1.410 (5)
C7—H7B0.9700C20'—H20'0.9300
C8—H80.96 (3)C21'—H21'0.9300
C9—C101.335 (5)
C12—Fe—C17108.1 (3)N2—C9—H9118 (2)
C12—Fe—C17'106.2 (5)C9—C10—N1106.9 (3)
C17—Fe—C17'15.9 (4)C9—C10—H10132 (3)
C12—Fe—C18124.2 (3)N1—C10—H10121 (3)
C17—Fe—C1840.92 (17)N2—C11—C12110.8 (3)
C17'—Fe—C1855.5 (4)N2—C11—H11A109.5
C12—Fe—C21122.9 (4)C12—C11—H11A109.5
C17—Fe—C2140.9 (3)N2—C11—H11B109.5
C17'—Fe—C2128.9 (6)C12—C11—H11B109.5
C18—Fe—C2168.5 (4)H11A—C11—H11B108.1
C12—Fe—C1341.10 (12)C13—C12—C16107.1 (3)
C17—Fe—C13122.6 (4)C13—C12—C11127.9 (3)
C17'—Fe—C13131.5 (6)C16—C12—C11125.0 (3)
C18—Fe—C13107.4 (2)C13—C12—Fe70.00 (18)
C21—Fe—C13159.0 (4)C16—C12—Fe70.50 (18)
C12—Fe—C19'143.7 (7)C11—C12—Fe124.8 (2)
C17—Fe—C19'56.8 (5)C14—C13—C12109.0 (3)
C17'—Fe—C19'68.1 (5)C14—C13—Fe70.24 (18)
C18—Fe—C19'22.5 (4)C12—C13—Fe68.90 (17)
C21—Fe—C19'69.9 (6)C14—C13—H13125.5
C13—Fe—C19'114.7 (5)C12—C13—H13125.5
C12—Fe—C20158.0 (3)Fe—C13—H13127.0
C17—Fe—C2068.9 (4)C13—C14—C15107.7 (3)
C17'—Fe—C2064.7 (6)C13—C14—Fe69.55 (18)
C18—Fe—C2068.8 (3)C15—C14—Fe70.26 (19)
C21—Fe—C2040.6 (2)C13—C14—H14126.1
C13—Fe—C20158.9 (4)C15—C14—H14126.1
C19'—Fe—C2054.2 (5)Fe—C14—H14125.6
C12—Fe—C1468.95 (13)C14—C15—C16108.4 (3)
C17—Fe—C14156.9 (4)C14—C15—Fe69.28 (19)
C17'—Fe—C14171.2 (6)C16—C15—Fe69.40 (18)
C18—Fe—C14120.5 (3)C14—C15—H15125.8
C21—Fe—C14159.9 (4)C16—C15—H15125.8
C13—Fe—C1440.20 (13)Fe—C15—H15127.1
C19'—Fe—C14111.1 (4)C15—C16—C12107.7 (3)
C20—Fe—C14122.5 (4)C15—C16—Fe70.12 (19)
C12—Fe—C1641.04 (12)C12—C16—Fe68.47 (18)
C17—Fe—C16125.3 (3)C15—C16—H16126.1
C17'—Fe—C16113.1 (5)C12—C16—H16126.1
C18—Fe—C16161.8 (3)Fe—C16—H16126.8
C21—Fe—C16108.7 (4)C21—C17—C18107.7 (5)
C13—Fe—C1668.33 (13)C21—C17—Fe69.9 (8)
C19'—Fe—C16175.2 (7)C18—C17—Fe69.8 (5)
C20—Fe—C16121.7 (3)C21—C17—H17126.2
C14—Fe—C1668.46 (14)C18—C17—H17126.2
C12—Fe—C19160.5 (3)Fe—C17—H17125.7
C17—Fe—C1967.9 (3)C19—C18—C17107.4 (4)
C17'—Fe—C1975.2 (5)C19—C18—Fe70.6 (4)
C18—Fe—C1940.32 (13)C17—C18—Fe69.3 (6)
C21—Fe—C1967.5 (4)C19—C18—H18126.3
C13—Fe—C19123.6 (2)C17—C18—H18126.3
C19'—Fe—C1918.4 (5)Fe—C18—H18125.4
C20—Fe—C1940.28 (15)C18—C19—C20109.4 (5)
C14—Fe—C19106.8 (2)C18—C19—Fe69.0 (4)
C16—Fe—C19156.8 (3)C20—C19—Fe69.4 (5)
C12—Fe—C21'132.4 (7)C18—C19—H19125.3
C17—Fe—C21'50.7 (8)C20—C19—H19125.3
C17'—Fe—C21'40.6 (5)Fe—C19—H19127.9
C18—Fe—C21'71.2 (9)C19—C20—C21106.9 (5)
C21—Fe—C21'12.5 (7)C19—C20—Fe70.3 (5)
C13—Fe—C21'171.5 (7)C21—C20—Fe69.4 (8)
C19'—Fe—C21'67.3 (9)C19—C20—H20126.6
C20—Fe—C21'29.0 (7)C21—C20—H20126.6
C14—Fe—C21'147.9 (7)Fe—C20—H20125.3
C16—Fe—C21'110.3 (9)C20—C21—C17108.6 (5)
C19—Fe—C21'61.0 (8)C20—C21—Fe70.0 (7)
C8—N1—C10108.5 (3)C17—C21—Fe69.2 (8)
C8—N1—C7124.9 (3)C20—C21—H21125.7
C10—N1—C7126.6 (3)C17—C21—H21125.7
C8—N2—C9107.9 (3)Fe—C21—H21126.7
C8—N2—C11125.7 (3)C21'—C17'—C18'107.6 (5)
C9—N2—C11126.2 (3)C21'—C17'—Fe71 (2)
C2—C1—C6120.6 (4)C18'—C17'—Fe71.5 (12)
C2—C1—H1119.7C21'—C17'—H17'126.2
C6—C1—H1119.7C18'—C17'—H17'126.2
C3—C2—C1120.2 (4)Fe—C17'—H17'123.3
C3—C2—H2119.9C19'—C18'—C17'107.3 (5)
C1—C2—H2119.9C19'—C18'—Fe68.5 (10)
C4—C3—C2120.5 (4)C17'—C18'—Fe68.1 (12)
C4—C3—H3119.8C19'—C18'—H18'126.3
C2—C3—H3119.8C17'—C18'—H18'126.3
C3—C4—C5119.6 (4)Fe—C18'—H18'128.6
C3—C4—H4120.2C18'—C19'—C20'109.3 (5)
C5—C4—H4120.2C18'—C19'—Fe71.5 (10)
C4—C5—C6120.7 (4)C20'—C19'—Fe73.3 (13)
C4—C5—H5119.6C18'—C19'—H19'125.4
C6—C5—H5119.6C20'—C19'—H19'125.4
C5—C6—C1118.4 (3)Fe—C19'—H19'121.5
C5—C6—C7123.2 (3)C19'—C20'—C21'106.8 (6)
C1—C6—C7118.4 (3)C19'—C20'—Fe67.1 (12)
N1—C7—C6113.6 (3)C21'—C20'—Fe67.9 (19)
N1—C7—H7A108.9C19'—C20'—H20'126.6
C6—C7—H7A108.9C21'—C20'—H20'126.6
N1—C7—H7B108.9Fe—C20'—H20'130.0
C6—C7—H7B108.9C20'—C21'—C17'108.6 (6)
H7A—C7—H7B107.7C20'—C21'—Fe72.5 (17)
N1—C8—N2109.0 (3)C17'—C21'—Fe68.7 (17)
N1—C8—H8123.8 (17)C20'—C21'—H21'125.7
N2—C8—H8127.2 (17)C17'—C21'—H21'125.7
C10—C9—N2107.6 (3)Fe—C21'—H21'124.6
C10—C9—H9134 (3)
C6—C1—C2—C30.4 (6)C14—Fe—C18—C17162.0 (6)
C1—C2—C3—C40.9 (6)C16—Fe—C18—C1746.7 (9)
C2—C3—C4—C50.4 (6)C19—Fe—C18—C17118.1 (6)
C3—C4—C5—C60.5 (6)C21'—Fe—C18—C1751.1 (8)
C4—C5—C6—C11.0 (5)C17—C18—C19—C202.1 (11)
C4—C5—C6—C7178.3 (3)Fe—C18—C19—C2057.7 (7)
C2—C1—C6—C50.5 (5)C17—C18—C19—Fe59.8 (8)
C2—C1—C6—C7178.0 (3)C12—Fe—C19—C1843.3 (8)
C8—N1—C7—C6105.1 (4)C17—Fe—C19—C1838.6 (3)
C10—N1—C7—C675.5 (5)C17'—Fe—C19—C1853.5 (6)
C5—C6—C7—N127.2 (5)C21—Fe—C19—C1882.9 (4)
C1—C6—C7—N1155.5 (3)C13—Fe—C19—C1876.8 (5)
C10—N1—C8—N20.2 (4)C19'—Fe—C19—C1811.0 (15)
C7—N1—C8—N2179.2 (3)C20—Fe—C19—C18121.6 (6)
C9—N2—C8—N10.4 (4)C14—Fe—C19—C18117.6 (4)
C11—N2—C8—N1176.2 (3)C16—Fe—C19—C18168.1 (5)
C8—N2—C9—C100.8 (4)C21'—Fe—C19—C1894.8 (9)
C11—N2—C9—C10176.6 (3)C12—Fe—C19—C20164.9 (7)
N2—C9—C10—N10.9 (5)C17—Fe—C19—C2083.0 (5)
C8—N1—C10—C90.7 (4)C17'—Fe—C19—C2068.1 (7)
C7—N1—C10—C9178.7 (3)C18—Fe—C19—C20121.6 (6)
C8—N2—C11—C1265.1 (5)C21—Fe—C19—C2038.7 (4)
C9—N2—C11—C12110.0 (4)C13—Fe—C19—C20161.6 (6)
N2—C11—C12—C1399.8 (4)C19'—Fe—C19—C20132.6 (16)
N2—C11—C12—C1680.1 (4)C14—Fe—C19—C20120.8 (6)
N2—C11—C12—Fe169.5 (2)C16—Fe—C19—C2046.5 (8)
C17—Fe—C12—C13119.2 (4)C21'—Fe—C19—C2026.8 (10)
C17'—Fe—C12—C13135.7 (6)C18—C19—C20—C212.6 (14)
C18—Fe—C12—C1376.8 (4)Fe—C19—C20—C2160.1 (10)
C21—Fe—C12—C13161.8 (5)C18—C19—C20—Fe57.5 (6)
C19'—Fe—C12—C1360.9 (7)C12—Fe—C20—C19166.6 (6)
C20—Fe—C12—C13162.4 (9)C17—Fe—C20—C1980.3 (4)
C14—Fe—C12—C1336.51 (19)C17'—Fe—C20—C1997.0 (6)
C16—Fe—C12—C13117.5 (3)C18—Fe—C20—C1936.3 (4)
C19—Fe—C12—C1344.3 (7)C21—Fe—C20—C19117.7 (8)
C21'—Fe—C12—C13172.0 (12)C13—Fe—C20—C1947.0 (11)
C17—Fe—C12—C16123.4 (4)C19'—Fe—C20—C1916.7 (6)
C17'—Fe—C12—C16106.8 (6)C14—Fe—C20—C1977.2 (6)
C18—Fe—C12—C16165.8 (4)C16—Fe—C20—C19160.4 (4)
C21—Fe—C12—C1680.7 (5)C21'—Fe—C20—C19125 (2)
C13—Fe—C12—C16117.5 (3)C12—Fe—C20—C2149.0 (11)
C19'—Fe—C12—C16178.4 (7)C17—Fe—C20—C2137.4 (6)
C20—Fe—C12—C1644.9 (9)C17'—Fe—C20—C2120.6 (7)
C14—Fe—C12—C1681.0 (2)C18—Fe—C20—C2181.4 (6)
C19—Fe—C12—C16161.8 (6)C13—Fe—C20—C21164.7 (8)
C21'—Fe—C12—C1670.5 (12)C19'—Fe—C20—C21101.0 (8)
C17—Fe—C12—C113.8 (5)C14—Fe—C20—C21165.2 (6)
C17'—Fe—C12—C1112.8 (7)C16—Fe—C20—C2182.0 (7)
C18—Fe—C12—C1146.1 (5)C19—Fe—C20—C21117.7 (8)
C21—Fe—C12—C1138.9 (6)C21'—Fe—C20—C218 (2)
C13—Fe—C12—C11122.9 (4)C19—C20—C21—C172.1 (17)
C19'—Fe—C12—C1162.0 (8)Fe—C20—C21—C1758.6 (12)
C20—Fe—C12—C1174.7 (9)C19—C20—C21—Fe60.6 (8)
C14—Fe—C12—C11159.4 (3)C18—C17—C21—C200.8 (18)
C16—Fe—C12—C11119.6 (4)Fe—C17—C21—C2059.0 (11)
C19—Fe—C12—C1178.6 (7)C18—C17—C21—Fe59.8 (9)
C21'—Fe—C12—C1149.1 (12)C12—Fe—C21—C20160.4 (4)
C16—C12—C13—C142.1 (4)C17—Fe—C21—C20120.1 (9)
C11—C12—C13—C14178.0 (3)C17'—Fe—C21—C20138.8 (14)
Fe—C12—C13—C1458.9 (2)C18—Fe—C21—C2082.0 (6)
C16—C12—C13—Fe61.1 (2)C13—Fe—C21—C20164.6 (7)
C11—C12—C13—Fe119.1 (3)C19'—Fe—C21—C2057.9 (7)
C12—Fe—C13—C14120.7 (3)C14—Fe—C21—C2038.8 (15)
C17—Fe—C13—C14159.2 (4)C16—Fe—C21—C20117.2 (6)
C17'—Fe—C13—C14175.9 (7)C19—Fe—C21—C2038.3 (5)
C18—Fe—C13—C14116.9 (4)C21'—Fe—C21—C2018 (5)
C21—Fe—C13—C14167.8 (11)C12—Fe—C21—C1779.5 (7)
C19'—Fe—C13—C1494.1 (7)C17'—Fe—C21—C1718.7 (12)
C20—Fe—C13—C1441.0 (8)C18—Fe—C21—C1738.1 (5)
C16—Fe—C13—C1481.8 (2)C13—Fe—C21—C1744.5 (14)
C19—Fe—C13—C1475.6 (4)C19'—Fe—C21—C1762.2 (7)
C21'—Fe—C13—C14164 (6)C20—Fe—C21—C17120.1 (9)
C17—Fe—C13—C1280.1 (4)C14—Fe—C21—C17158.9 (9)
C17'—Fe—C13—C1263.5 (7)C16—Fe—C21—C17122.7 (6)
C18—Fe—C13—C12122.4 (4)C19—Fe—C21—C1781.8 (6)
C21—Fe—C13—C1247.1 (11)C21'—Fe—C21—C17138 (6)
C19'—Fe—C13—C12145.3 (7)C12—Fe—C17'—C21'137.8 (14)
C20—Fe—C13—C12161.6 (7)C17—Fe—C17'—C21'123 (3)
C14—Fe—C13—C12120.7 (3)C18—Fe—C17'—C21'101.5 (14)
C16—Fe—C13—C1238.82 (19)C21—Fe—C17'—C21'8 (2)
C19—Fe—C13—C12163.8 (3)C13—Fe—C17'—C21'175.6 (13)
C21'—Fe—C13—C1244 (6)C19'—Fe—C17'—C21'80.2 (13)
C12—C13—C14—C152.1 (4)C20—Fe—C17'—C21'20.8 (13)
Fe—C13—C14—C1560.2 (2)C14—Fe—C17'—C21'167 (3)
C12—C13—C14—Fe58.1 (2)C16—Fe—C17'—C21'94.7 (14)
C12—Fe—C14—C1337.30 (19)C19—Fe—C17'—C21'62.4 (14)
C17—Fe—C14—C1349.7 (8)C12—Fe—C17'—C18'105.1 (10)
C17'—Fe—C14—C1321 (3)C17—Fe—C17'—C18'6 (2)
C18—Fe—C14—C1380.9 (4)C18—Fe—C17'—C18'15.6 (7)
C21—Fe—C14—C13167.3 (12)C21—Fe—C17'—C18'124.6 (16)
C19'—Fe—C14—C13103.6 (8)C13—Fe—C17'—C18'67.4 (11)
C20—Fe—C14—C13163.8 (3)C19'—Fe—C17'—C18'36.8 (7)
C16—Fe—C14—C1381.5 (2)C20—Fe—C17'—C18'96.3 (10)
C19—Fe—C14—C13122.6 (3)C14—Fe—C17'—C18'50 (3)
C21'—Fe—C14—C13175.7 (16)C16—Fe—C17'—C18'148.2 (9)
C12—Fe—C14—C1581.3 (2)C19—Fe—C17'—C18'54.7 (9)
C17—Fe—C14—C15168.3 (8)C21'—Fe—C17'—C18'117.0 (15)
C17'—Fe—C14—C15139 (3)C21'—C17'—C18'—C19'4 (3)
C18—Fe—C14—C15160.5 (3)Fe—C17'—C18'—C19'57.4 (15)
C21—Fe—C14—C1548.7 (12)C21'—C17'—C18'—Fe62 (3)
C13—Fe—C14—C15118.6 (3)C12—Fe—C18'—C19'150.4 (8)
C19'—Fe—C14—C15137.7 (8)C17—Fe—C18'—C19'124.0 (15)
C20—Fe—C14—C1577.6 (4)C17'—Fe—C18'—C19'120.2 (11)
C16—Fe—C14—C1537.1 (2)C18—Fe—C18'—C19'16.8 (14)
C19—Fe—C14—C15118.8 (3)C21—Fe—C18'—C19'93.1 (9)
C21'—Fe—C14—C1557.1 (17)C13—Fe—C18'—C19'106.6 (9)
C13—C14—C15—C161.2 (4)C20—Fe—C18'—C19'51.6 (8)
Fe—C14—C15—C1658.5 (2)C14—Fe—C18'—C19'69.1 (9)
C13—C14—C15—Fe59.7 (2)C16—Fe—C18'—C19'175.0 (8)
C12—Fe—C15—C1482.2 (2)C19—Fe—C18'—C19'11.9 (8)
C17—Fe—C15—C14165.4 (11)C21'—Fe—C18'—C19'81.3 (7)
C17'—Fe—C15—C14169.7 (9)C12—Fe—C18'—C17'89.4 (10)
C18—Fe—C15—C1444.8 (5)C17—Fe—C18'—C17'3.7 (14)
C21—Fe—C15—C14161.7 (5)C18—Fe—C18'—C17'137.0 (19)
C13—Fe—C15—C1437.80 (19)C21—Fe—C18'—C17'27.1 (9)
C19'—Fe—C15—C1465.1 (8)C13—Fe—C18'—C17'133.2 (10)
C20—Fe—C15—C14120.6 (4)C19'—Fe—C18'—C17'120.2 (11)
C16—Fe—C15—C14120.2 (3)C20—Fe—C18'—C17'68.6 (10)
C19—Fe—C15—C1479.0 (3)C14—Fe—C18'—C17'170.7 (8)
C21'—Fe—C15—C14149.9 (8)C16—Fe—C18'—C17'54.8 (12)
C12—Fe—C15—C1637.92 (19)C19—Fe—C18'—C17'108.3 (10)
C17—Fe—C15—C1645.3 (11)C21'—Fe—C18'—C17'38.9 (8)
C17'—Fe—C15—C1649.6 (9)C17'—C18'—C19'—C20'7 (3)
C18—Fe—C15—C16165.0 (5)Fe—C18'—C19'—C20'64.0 (19)
C21—Fe—C15—C1678.1 (5)C17'—C18'—C19'—Fe57.2 (17)
C13—Fe—C15—C1682.4 (2)C12—Fe—C19'—C18'50.5 (11)
C19'—Fe—C15—C16174.8 (8)C17—Fe—C19'—C18'24.3 (7)
C20—Fe—C15—C16119.3 (4)C17'—Fe—C19'—C18'37.2 (7)
C14—Fe—C15—C16120.2 (3)C18—Fe—C19'—C18'14.2 (10)
C19—Fe—C15—C16160.9 (3)C21—Fe—C19'—C18'68.1 (8)
C21'—Fe—C15—C1689.9 (8)C13—Fe—C19'—C18'89.7 (8)
C14—C15—C16—C120.1 (4)C20—Fe—C19'—C18'111.0 (10)
Fe—C15—C16—C1258.3 (2)C14—Fe—C19'—C18'133.4 (8)
C14—C15—C16—Fe58.5 (2)C16—Fe—C19'—C18'142 (5)
C13—C12—C16—C151.4 (4)C19—Fe—C19'—C18'147 (2)
C11—C12—C16—C15178.7 (3)C21'—Fe—C19'—C18'81.2 (8)
Fe—C12—C16—C1559.4 (2)C12—Fe—C19'—C20'168.2 (12)
C13—C12—C16—Fe60.7 (2)C17—Fe—C19'—C20'93.3 (11)
C11—C12—C16—Fe119.4 (3)C17'—Fe—C19'—C20'80.5 (9)
C12—Fe—C16—C15119.4 (3)C18—Fe—C19'—C20'131.9 (14)
C17—Fe—C16—C15164.1 (5)C21—Fe—C19'—C20'49.5 (11)
C17'—Fe—C16—C15152.3 (6)C13—Fe—C19'—C20'152.6 (11)
C18—Fe—C16—C15160.2 (7)C20—Fe—C19'—C20'6.6 (13)
C21—Fe—C16—C15121.6 (5)C14—Fe—C19'—C20'109.0 (11)
C13—Fe—C16—C1580.5 (2)C16—Fe—C19'—C20'25 (5)
C19'—Fe—C16—C1549 (5)C19—Fe—C19'—C20'29.4 (19)
C20—Fe—C16—C1578.7 (5)C21'—Fe—C19'—C20'36.4 (9)
C14—Fe—C16—C1537.10 (19)C18'—C19'—C20'—C21'7 (4)
C19—Fe—C16—C1545.3 (6)Fe—C19'—C20'—C21'56 (3)
C21'—Fe—C16—C15108.5 (8)C18'—C19'—C20'—Fe62.8 (16)
C17—Fe—C16—C1276.5 (5)C12—Fe—C20'—C19'119 (4)
C17'—Fe—C16—C1288.3 (6)C17—Fe—C20'—C19'65.2 (9)
C18—Fe—C16—C1240.8 (7)C17'—Fe—C20'—C19'82.5 (9)
C21—Fe—C16—C12119.0 (5)C18—Fe—C20'—C19'19.9 (7)
C13—Fe—C16—C1238.88 (19)C21—Fe—C20'—C19'109.3 (12)
C19'—Fe—C16—C12168 (5)C13—Fe—C20'—C19'49.6 (16)
C20—Fe—C16—C12161.9 (5)C20—Fe—C20'—C19'159 (4)
C14—Fe—C16—C1282.3 (2)C14—Fe—C20'—C19'89.8 (11)
C19—Fe—C16—C12164.7 (5)C16—Fe—C20'—C19'177.1 (8)
C21'—Fe—C16—C12132.1 (8)C19—Fe—C20'—C19'21.5 (11)
C12—Fe—C17—C21119.7 (7)C21'—Fe—C20'—C19'120.7 (17)
C17'—Fe—C17—C2134 (3)C12—Fe—C20'—C21'2 (5)
C18—Fe—C17—C21118.6 (8)C17—Fe—C20'—C21'55.5 (13)
C13—Fe—C17—C21162.7 (6)C17'—Fe—C20'—C21'38.2 (13)
C19'—Fe—C17—C2197.3 (9)C18—Fe—C20'—C21'100.8 (15)
C20—Fe—C17—C2137.1 (6)C21—Fe—C20'—C21'11.4 (16)
C14—Fe—C17—C21161.5 (9)C13—Fe—C20'—C21'170.4 (14)
C16—Fe—C17—C2177.5 (7)C19'—Fe—C20'—C21'120.7 (17)
C19—Fe—C17—C2180.6 (6)C20—Fe—C20'—C21'39 (3)
C21'—Fe—C17—C2110.8 (13)C14—Fe—C20'—C21'149.5 (14)
C12—Fe—C17—C18121.6 (5)C16—Fe—C20'—C21'62.1 (16)
C17'—Fe—C17—C18153 (3)C19—Fe—C20'—C21'142 (2)
C21—Fe—C17—C18118.6 (8)C19'—C20'—C21'—C17'4 (4)
C13—Fe—C17—C1878.7 (6)Fe—C20'—C21'—C17'60 (3)
C19'—Fe—C17—C1821.3 (6)C19'—C20'—C21'—Fe56 (2)
C20—Fe—C17—C1881.5 (4)C18'—C17'—C21'—C20'0 (4)
C14—Fe—C17—C1842.9 (11)Fe—C17'—C21'—C20'62 (3)
C16—Fe—C17—C18163.9 (4)C18'—C17'—C21'—Fe62 (2)
C19—Fe—C17—C1838.0 (4)C12—Fe—C21'—C20'179.6 (10)
C21'—Fe—C17—C18107.9 (12)C17—Fe—C21'—C20'101.4 (16)
C21—C17—C18—C190.8 (15)C17'—Fe—C21'—C20'119 (2)
Fe—C17—C18—C1960.7 (6)C18—Fe—C21'—C20'60.1 (12)
C21—C17—C18—Fe59.9 (11)C21—Fe—C21'—C20'136 (6)
C12—Fe—C18—C19163.9 (4)C13—Fe—C21'—C20'142 (5)
C17—Fe—C18—C19118.1 (6)C19'—Fe—C21'—C20'36.4 (11)
C17'—Fe—C18—C19109.4 (7)C20—Fe—C21'—C20'19.8 (14)
C21—Fe—C18—C1980.0 (4)C14—Fe—C21'—C20'58 (2)
C13—Fe—C18—C19121.8 (4)C16—Fe—C21'—C20'139.1 (12)
C19'—Fe—C18—C199.0 (13)C19—Fe—C21'—C20'17.2 (10)
C20—Fe—C18—C1936.2 (3)C12—Fe—C21'—C17'60.9 (18)
C14—Fe—C18—C1979.9 (4)C17—Fe—C21'—C17'17.4 (9)
C16—Fe—C18—C19164.8 (5)C18—Fe—C21'—C17'58.6 (11)
C21'—Fe—C18—C1967.0 (7)C21—Fe—C21'—C17'17 (5)
C12—Fe—C18—C1777.9 (6)C13—Fe—C21'—C17'23 (7)
C17'—Fe—C18—C178.7 (9)C19'—Fe—C21'—C17'82.3 (12)
C21—Fe—C18—C1738.1 (4)C20—Fe—C21'—C17'139 (3)
C13—Fe—C18—C17120.1 (6)C14—Fe—C21'—C17'176.2 (8)
C19'—Fe—C18—C17127.2 (13)C16—Fe—C21'—C17'102.2 (13)
C20—Fe—C18—C1781.9 (5)C19—Fe—C21'—C17'101.5 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···I0.96 (3)3.00 (3)3.876 (4)152 (2)
 

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