1-(Ferrocen-1-ylmeth-yl)-3-methyl-imidazol-3-ium iodide.

The structure of the title compound, [Fe(C5H5)(C10H12N2)]I, consists of a 1-(ferrocen-1-ylmeth-yl)-3-methyl-imidazolium cation which is counter-balanced by an iodide anion. The cyclo-penta-dienyl (Cp) rings of the ferrocene unit have a slightly staggered conformation skewed from an ideal eclipsed conformation by an angle of 3.5 (6)°. The inter-planar angle between the Cp and the imidazole ring is 67.94 (2)°.

Related literature

For the synthesis of ferrocenyl alkyl imidazoles, see: Simenel et al. (2003 ▶); Nyamori & Bala (2008 ▶). For the synthesis of ferrocenyl imidazolium salts, see: Nyamori et al. (2010 ▶, 2012 ▶); Bala & Coville (2007 ▶). For applications of ferrocenyl imidazolium salts, see: Gao et al. (2004 ▶); Ornelas (2011 ▶); Coleman et al. (2005 ▶); Taylor & Licence (2012 ▶).

Experimental

Crystal data

[Fe(C5H5)(C10H12N2)]I

M = 408.06

Monoclinic,

a = 7.2745 (3) Å

b = 9.3164 (3) Å

c = 22.2744 (9) Å

β = 90.927 (3)°

V = 1509.39 (10) Å3

Z = 4

Cu Kα radiation

μ = 23.96 mm−1

T = 173 K

0.16 × 0.12 × 0.07 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), based on expressions of Clark & Reid (1995 ▶)] T min = 0.114, T max = 0.285

6978 measured reflections

2972 independent reflections

2745 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.134

S = 1.20

2972 reflections

173 parameters

H-atom parameters constrained

Δρmax = 2.51 e Å−3

Δρmin = −1.53 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: 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: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045400/hg5258sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045400/hg5258Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C5H5)(C10H12N2)]I	F(000) = 800
Mr = 408.06	Dx = 1.796 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 7295 reflections
a = 7.2745 (3) Å	θ = 4.0–74°
b = 9.3164 (3) Å	µ = 23.96 mm−1
c = 22.2744 (9) Å	T = 173 K
β = 90.927 (3)°	Block, yellow
V = 1509.39 (10) Å3	0.16 × 0.12 × 0.07 mm
Z = 4

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2745 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.042
ω scans	θmax = 74°, θmin = 4.0°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions of Clark & Reid (1995)]	h = −6→8
Tmin = 0.114, Tmax = 0.285	k = −10→11
6978 measured reflections	l = −19→27
2972 independent 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0682P)2 + 3.7636P] where P = (Fo2 + 2Fc2)/3
2972 reflections	(Δ/σ)max = 0.011
173 parameters	Δρmax = 2.51 e Å−3
0 restraints	Δρmin = −1.53 e Å−3

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
C1	0.3124 (13)	−0.0474 (8)	0.7098 (3)	0.0455 (18)
H1	0.3738	−0.1201	0.6839	0.055*
C2	0.4011 (13)	0.0604 (11)	0.7444 (4)	0.056 (2)
H2	0.5369	0.0768	0.7472	0.067*
C3	0.2664 (16)	0.1406 (10)	0.7745 (4)	0.059 (3)
H3	0.2886	0.223	0.8025	0.071*
C4	0.0912 (15)	0.0802 (9)	0.7577 (4)	0.058 (2)
H4	−0.0314	0.1148	0.7714	0.07*
C5	0.1209 (13)	−0.0329 (8)	0.7183 (4)	0.0477 (19)
H5	0.0231	−0.0932	0.6988	0.057*
C6	0.2546 (8)	0.3596 (6)	0.6585 (3)	0.0260 (12)
H6	0.2877	0.4416	0.6855	0.031*
C7	0.0720 (8)	0.3107 (7)	0.6449 (3)	0.0284 (12)
H7	−0.0445	0.3519	0.6608	0.034*
C8	0.0869 (8)	0.1903 (7)	0.6049 (3)	0.0276 (12)
H8	−0.0176	0.1321	0.5883	0.033*
C9	0.2748 (8)	0.1664 (6)	0.5945 (3)	0.0244 (11)
H9	0.3262	0.0884	0.5689	0.029*
C10	0.3810 (8)	0.2713 (6)	0.6275 (3)	0.0243 (11)
C11	0.5858 (8)	0.2808 (6)	0.6288 (3)	0.0254 (12)
H11A	0.6262	0.342	0.6629	0.031*
H11B	0.6384	0.1839	0.635	0.031*
C12	0.6907 (8)	0.2666 (6)	0.5229 (3)	0.0258 (11)
H12	0.6752	0.1659	0.5186	0.031*
C13	0.6956 (8)	0.4835 (7)	0.5609 (3)	0.0294 (13)
H13	0.6849	0.5608	0.5885	0.035*
C14	0.7537 (8)	0.4932 (7)	0.5038 (3)	0.0278 (12)
H14	0.7892	0.578	0.4833	0.033*
C15	0.8032 (9)	0.3090 (9)	0.4206 (3)	0.0357 (15)
H15A	0.9338	0.2831	0.4207	0.053*
H15B	0.7813	0.3881	0.3924	0.053*
H15C	0.7293	0.2257	0.4083	0.053*
N1	0.6545 (7)	0.3416 (5)	0.5722 (2)	0.0233 (10)
N2	0.7512 (7)	0.3536 (6)	0.4809 (2)	0.0274 (10)
Fe1	0.22750 (13)	0.15195 (10)	0.68399 (4)	0.0244 (2)
I1	0.69574 (5)	−0.11859 (4)	0.579436 (17)	0.02780 (16)

	U11	U22	U33	U12	U13	U23
C1	0.080 (6)	0.023 (3)	0.034 (3)	0.010 (3)	0.005 (3)	0.010 (3)
C2	0.060 (5)	0.059 (6)	0.047 (4)	−0.006 (4)	−0.016 (4)	0.032 (4)
C3	0.115 (8)	0.036 (4)	0.026 (3)	−0.014 (5)	−0.005 (4)	0.003 (3)
C4	0.086 (6)	0.035 (4)	0.054 (5)	−0.004 (4)	0.037 (5)	0.016 (4)
C5	0.071 (5)	0.023 (3)	0.049 (4)	−0.016 (3)	0.009 (4)	0.008 (3)
C6	0.030 (3)	0.017 (3)	0.031 (3)	−0.004 (2)	0.000 (2)	0.000 (2)
C7	0.025 (3)	0.022 (3)	0.037 (3)	0.001 (2)	0.000 (2)	0.001 (2)
C8	0.027 (3)	0.025 (3)	0.031 (3)	−0.007 (2)	−0.001 (2)	0.002 (2)
C9	0.030 (3)	0.015 (3)	0.028 (3)	0.000 (2)	0.000 (2)	0.000 (2)
C10	0.026 (3)	0.017 (3)	0.030 (3)	−0.003 (2)	0.000 (2)	0.003 (2)
C11	0.023 (3)	0.021 (3)	0.032 (3)	0.004 (2)	0.000 (2)	0.005 (2)
C12	0.024 (3)	0.016 (3)	0.037 (3)	0.003 (2)	−0.001 (2)	−0.002 (2)
C13	0.029 (3)	0.014 (3)	0.045 (4)	−0.002 (2)	−0.001 (2)	0.001 (2)
C14	0.023 (3)	0.016 (3)	0.045 (3)	−0.001 (2)	0.003 (2)	0.003 (2)
C15	0.041 (4)	0.035 (4)	0.032 (3)	0.001 (3)	0.006 (3)	0.002 (3)
N1	0.023 (2)	0.014 (2)	0.033 (3)	0.0008 (18)	−0.0016 (18)	0.0024 (19)
N2	0.026 (2)	0.021 (2)	0.035 (3)	0.002 (2)	−0.0005 (19)	0.004 (2)
Fe1	0.0326 (5)	0.0163 (4)	0.0243 (4)	−0.0031 (4)	0.0020 (3)	−0.0002 (3)
I1	0.0357 (2)	0.0139 (2)	0.0336 (2)	0.00001 (13)	−0.00212 (15)	0.00010 (12)

C1—C2	1.416 (13)	C8—Fe1	2.054 (6)
C1—C5	1.415 (13)	C8—H8	1
C1—Fe1	2.036 (7)	C9—C10	1.441 (8)
C1—H1	1	C9—Fe1	2.033 (6)
C2—C3	1.410 (15)	C9—H9	1
C2—Fe1	2.020 (8)	C10—C11	1.492 (8)
C2—H2	1	C10—Fe1	2.028 (6)
C3—C4	1.438 (15)	C11—N1	1.476 (7)
C3—Fe1	2.034 (8)	C11—H11A	0.99
C3—H3	1	C11—H11B	0.99
C4—C5	1.390 (12)	C12—N2	1.319 (8)
C4—Fe1	2.044 (7)	C12—N1	1.333 (8)
C4—H4	1	C12—H12	0.95
C5—Fe1	2.042 (7)	C13—C14	1.350 (9)
C5—H5	1	C13—N1	1.380 (7)
C6—C10	1.420 (8)	C13—H13	0.95
C6—C7	1.432 (8)	C14—N2	1.397 (8)
C6—Fe1	2.027 (6)	C14—H14	0.95
C6—H6	1	C15—N2	1.461 (8)
C7—C8	1.437 (9)	C15—H15A	0.98
C7—Fe1	2.048 (6)	C15—H15B	0.98
C7—H7	1	C15—H15C	0.98
C8—C9	1.408 (8)
C2—C1—C5	107.5 (7)	N2—C12—N1	109.6 (5)
C2—C1—Fe1	68.9 (4)	N2—C12—H12	125.2
C5—C1—Fe1	69.9 (4)	N1—C12—H12	125.2
C2—C1—H1	126.3	C14—C13—N1	108.0 (6)
C5—C1—H1	126.3	C14—C13—H13	126
Fe1—C1—H1	126.3	N1—C13—H13	126
C3—C2—C1	108.7 (8)	C13—C14—N2	106.2 (5)
C3—C2—Fe1	70.2 (5)	C13—C14—H14	126.9
C1—C2—Fe1	70.2 (4)	N2—C14—H14	126.9
C3—C2—H2	125.6	N2—C15—H15A	109.5
C1—C2—H2	125.6	N2—C15—H15B	109.5
Fe1—C2—H2	125.6	H15A—C15—H15B	109.5
C2—C3—C4	106.8 (8)	N2—C15—H15C	109.5
C2—C3—Fe1	69.1 (4)	H15A—C15—H15C	109.5
C4—C3—Fe1	69.7 (5)	H15B—C15—H15C	109.5
C2—C3—H3	126.6	C12—N1—C13	107.8 (5)
C4—C3—H3	126.6	C12—N1—C11	125.3 (5)
Fe1—C3—H3	126.6	C13—N1—C11	126.9 (5)
C5—C4—C3	108.4 (9)	C12—N2—C14	108.4 (5)
C5—C4—Fe1	70.0 (4)	C12—N2—C15	124.8 (6)
C3—C4—Fe1	69.0 (4)	C14—N2—C15	126.8 (6)
C5—C4—H4	125.8	C2—Fe1—C6	121.8 (3)
C3—C4—H4	125.8	C2—Fe1—C10	107.5 (3)
Fe1—C4—H4	125.8	C6—Fe1—C10	41.0 (2)
C4—C5—C1	108.7 (8)	C2—Fe1—C9	124.6 (3)
C4—C5—Fe1	70.2 (4)	C6—Fe1—C9	69.1 (2)
C1—C5—Fe1	69.5 (4)	C10—Fe1—C9	41.6 (2)
C4—C5—H5	125.7	C2—Fe1—C3	40.7 (4)
C1—C5—H5	125.7	C6—Fe1—C3	108.4 (3)
Fe1—C5—H5	125.7	C10—Fe1—C3	125.0 (3)
C10—C6—C7	108.6 (5)	C9—Fe1—C3	162.2 (4)
C10—C6—Fe1	69.5 (3)	C2—Fe1—C1	40.9 (4)
C7—C6—Fe1	70.2 (3)	C6—Fe1—C1	156.8 (3)
C10—C6—H6	125.7	C10—Fe1—C1	120.5 (3)
C7—C6—H6	125.7	C9—Fe1—C1	106.3 (3)
Fe1—C6—H6	125.7	C3—Fe1—C1	68.7 (3)
C6—C7—C8	107.5 (5)	C2—Fe1—C5	68.4 (4)
C6—C7—Fe1	68.6 (3)	C6—Fe1—C5	161.7 (3)
C8—C7—Fe1	69.7 (4)	C10—Fe1—C5	155.6 (3)
C6—C7—H7	126.3	C9—Fe1—C5	119.6 (3)
C8—C7—H7	126.3	C3—Fe1—C5	68.5 (3)
Fe1—C7—H7	126.3	C1—Fe1—C5	40.6 (4)
C9—C8—C7	108.0 (5)	C2—Fe1—C4	68.5 (4)
C9—C8—Fe1	69.0 (3)	C6—Fe1—C4	126.0 (3)
C7—C8—Fe1	69.3 (4)	C10—Fe1—C4	163.1 (3)
C9—C8—H8	126	C9—Fe1—C4	154.3 (4)
C7—C8—H8	126	C3—Fe1—C4	41.3 (4)
Fe1—C8—H8	126	C1—Fe1—C4	67.9 (4)
C8—C9—C10	108.8 (5)	C5—Fe1—C4	39.8 (3)
C8—C9—Fe1	70.7 (3)	C2—Fe1—C7	157.4 (4)
C10—C9—Fe1	69.0 (3)	C6—Fe1—C7	41.2 (2)
C8—C9—H9	125.6	C10—Fe1—C7	69.3 (2)
C10—C9—H9	125.6	C9—Fe1—C7	68.7 (2)
Fe1—C9—H9	125.6	C3—Fe1—C7	121.7 (4)
C6—C10—C9	107.1 (5)	C1—Fe1—C7	160.3 (3)
C6—C10—C11	127.6 (5)	C5—Fe1—C7	123.9 (3)
C9—C10—C11	125.2 (5)	C4—Fe1—C7	107.8 (3)
C6—C10—Fe1	69.5 (3)	C2—Fe1—C8	160.5 (4)
C9—C10—Fe1	69.4 (3)	C6—Fe1—C8	69.1 (2)
C11—C10—Fe1	125.5 (4)	C10—Fe1—C8	69.1 (2)
N1—C11—C10	111.0 (5)	C9—Fe1—C8	40.3 (2)
N1—C11—H11A	109.4	C3—Fe1—C8	156.7 (4)
C10—C11—H11A	109.4	C1—Fe1—C8	123.0 (3)
N1—C11—H11B	109.4	C5—Fe1—C8	106.3 (3)
C10—C11—H11B	109.4	C4—Fe1—C8	120.3 (4)
H11A—C11—H11B	108	C7—Fe1—C8	41.0 (3)
C5—C1—C2—C3	0.3 (8)	C8—C9—Fe1—C10	−120.0 (5)
Fe1—C1—C2—C3	59.8 (6)	C8—C9—Fe1—C3	−166.8 (10)
C5—C1—C2—Fe1	−59.5 (5)	C10—C9—Fe1—C3	−46.8 (11)
C1—C2—C3—C4	0.0 (9)	C8—C9—Fe1—C1	122.2 (4)
Fe1—C2—C3—C4	59.8 (6)	C10—C9—Fe1—C1	−117.8 (4)
C1—C2—C3—Fe1	−59.9 (5)	C8—C9—Fe1—C5	80.2 (5)
C2—C3—C4—C5	−0.3 (9)	C10—C9—Fe1—C5	−159.8 (4)
Fe1—C3—C4—C5	59.1 (6)	C8—C9—Fe1—C4	49.3 (9)
C2—C3—C4—Fe1	−59.4 (5)	C10—C9—Fe1—C4	169.3 (7)
C3—C4—C5—C1	0.5 (9)	C8—C9—Fe1—C7	−37.6 (4)
Fe1—C4—C5—C1	59.0 (5)	C10—C9—Fe1—C7	82.4 (4)
C3—C4—C5—Fe1	−58.5 (6)	C10—C9—Fe1—C8	120.0 (5)
C2—C1—C5—C4	−0.5 (9)	C4—C3—Fe1—C2	−118.1 (8)
Fe1—C1—C5—C4	−59.4 (6)	C2—C3—Fe1—C6	−117.8 (5)
C2—C1—C5—Fe1	58.9 (5)	C4—C3—Fe1—C6	124.2 (5)
C10—C6—C7—C8	0.0 (7)	C2—C3—Fe1—C10	−75.4 (6)
Fe1—C6—C7—C8	−59.1 (4)	C4—C3—Fe1—C10	166.6 (5)
C10—C6—C7—Fe1	59.1 (4)	C2—C3—Fe1—C9	−39.2 (13)
C6—C7—C8—C9	0.1 (7)	C4—C3—Fe1—C9	−157.2 (9)
Fe1—C7—C8—C9	−58.3 (4)	C2—C3—Fe1—C1	37.7 (6)
C6—C7—C8—Fe1	58.4 (4)	C4—C3—Fe1—C1	−80.4 (6)
C7—C8—C9—C10	−0.2 (7)	C2—C3—Fe1—C5	81.5 (6)
Fe1—C8—C9—C10	−58.6 (4)	C4—C3—Fe1—C5	−36.6 (5)
C7—C8—C9—Fe1	58.5 (4)	C2—C3—Fe1—C4	118.1 (8)
C7—C6—C10—C9	−0.1 (7)	C2—C3—Fe1—C7	−161.1 (5)
Fe1—C6—C10—C9	59.4 (4)	C4—C3—Fe1—C7	80.8 (6)
C7—C6—C10—C11	−179.1 (6)	C2—C3—Fe1—C8	162.7 (7)
Fe1—C6—C10—C11	−119.6 (6)	C4—C3—Fe1—C8	44.6 (10)
C7—C6—C10—Fe1	−59.5 (4)	C5—C1—Fe1—C2	118.9 (7)
C8—C9—C10—C6	0.2 (7)	C2—C1—Fe1—C6	49.5 (9)
Fe1—C9—C10—C6	−59.5 (4)	C5—C1—Fe1—C6	168.4 (6)
C8—C9—C10—C11	179.2 (5)	C2—C1—Fe1—C10	81.5 (6)
Fe1—C9—C10—C11	119.6 (6)	C5—C1—Fe1—C10	−159.6 (4)
C8—C9—C10—Fe1	59.7 (4)	C2—C1—Fe1—C9	124.4 (5)
C6—C10—C11—N1	−106.0 (7)	C5—C1—Fe1—C9	−116.7 (5)
C9—C10—C11—N1	75.1 (7)	C2—C1—Fe1—C3	−37.6 (6)
Fe1—C10—C11—N1	163.6 (4)	C5—C1—Fe1—C3	81.4 (6)
N1—C13—C14—N2	−1.3 (7)	C2—C1—Fe1—C5	−118.9 (7)
N2—C12—N1—C13	−0.4 (7)	C2—C1—Fe1—C4	−82.1 (6)
N2—C12—N1—C11	−179.5 (5)	C5—C1—Fe1—C4	36.8 (5)
C14—C13—N1—C12	1.1 (7)	C2—C1—Fe1—C7	−163.4 (8)
C14—C13—N1—C11	−179.9 (5)	C5—C1—Fe1—C7	−44.5 (10)
C10—C11—N1—C12	−86.7 (7)	C2—C1—Fe1—C8	165.2 (5)
C10—C11—N1—C13	94.4 (7)	C5—C1—Fe1—C8	−75.9 (5)
N1—C12—N2—C14	−0.4 (7)	C4—C5—Fe1—C2	81.9 (7)
N1—C12—N2—C15	−179.5 (5)	C1—C5—Fe1—C2	−38.0 (5)
C13—C14—N2—C12	1.1 (7)	C4—C5—Fe1—C6	−45.5 (13)
C13—C14—N2—C15	−179.8 (6)	C1—C5—Fe1—C6	−165.4 (8)
C3—C2—Fe1—C6	81.2 (6)	C4—C5—Fe1—C10	166.6 (7)
C1—C2—Fe1—C6	−159.3 (5)	C1—C5—Fe1—C10	46.7 (10)
C3—C2—Fe1—C10	123.8 (5)	C4—C5—Fe1—C9	−159.6 (6)
C1—C2—Fe1—C10	−116.7 (5)	C1—C5—Fe1—C9	80.5 (5)
C3—C2—Fe1—C9	166.5 (5)	C4—C5—Fe1—C3	37.9 (7)
C1—C2—Fe1—C9	−74.1 (6)	C1—C5—Fe1—C3	−82.0 (6)
C1—C2—Fe1—C3	119.5 (8)	C4—C5—Fe1—C1	119.9 (8)
C3—C2—Fe1—C1	−119.5 (8)	C1—C5—Fe1—C4	−119.9 (8)
C3—C2—Fe1—C5	−81.7 (6)	C4—C5—Fe1—C7	−76.7 (7)
C1—C2—Fe1—C5	37.8 (5)	C1—C5—Fe1—C7	163.4 (4)
C3—C2—Fe1—C4	−38.7 (6)	C4—C5—Fe1—C8	−118.0 (6)
C1—C2—Fe1—C4	80.7 (6)	C1—C5—Fe1—C8	122.1 (5)
C3—C2—Fe1—C7	45.9 (11)	C5—C4—Fe1—C2	−81.7 (6)
C1—C2—Fe1—C7	165.4 (7)	C3—C4—Fe1—C2	38.2 (6)
C3—C2—Fe1—C8	−159.4 (8)	C5—C4—Fe1—C6	163.9 (5)
C1—C2—Fe1—C8	−39.9 (12)	C3—C4—Fe1—C6	−76.2 (7)
C10—C6—Fe1—C2	79.9 (5)	C5—C4—Fe1—C10	−160.8 (10)
C7—C6—Fe1—C2	−160.3 (5)	C3—C4—Fe1—C10	−40.9 (15)
C7—C6—Fe1—C10	119.7 (5)	C5—C4—Fe1—C9	44.3 (11)
C10—C6—Fe1—C9	−38.6 (3)	C3—C4—Fe1—C9	164.2 (7)
C7—C6—Fe1—C9	81.1 (4)	C5—C4—Fe1—C3	−119.9 (9)
C10—C6—Fe1—C3	122.7 (5)	C5—C4—Fe1—C1	−37.5 (6)
C7—C6—Fe1—C3	−117.6 (5)	C3—C4—Fe1—C1	82.4 (6)
C10—C6—Fe1—C1	44.1 (8)	C3—C4—Fe1—C5	119.9 (9)
C7—C6—Fe1—C1	163.8 (7)	C5—C4—Fe1—C7	122.0 (6)
C10—C6—Fe1—C5	−160.5 (9)	C3—C4—Fe1—C7	−118.1 (6)
C7—C6—Fe1—C5	−40.7 (11)	C5—C4—Fe1—C8	78.9 (6)
C10—C6—Fe1—C4	165.2 (5)	C3—C4—Fe1—C8	−161.2 (5)
C7—C6—Fe1—C4	−75.1 (6)	C6—C7—Fe1—C2	48.2 (9)
C10—C6—Fe1—C7	−119.7 (5)	C8—C7—Fe1—C2	167.4 (8)
C10—C6—Fe1—C8	−81.9 (4)	C8—C7—Fe1—C6	119.2 (5)
C7—C6—Fe1—C8	37.8 (4)	C6—C7—Fe1—C10	−37.5 (4)
C6—C10—Fe1—C2	−118.7 (5)	C8—C7—Fe1—C10	81.7 (4)
C9—C10—Fe1—C2	122.8 (4)	C6—C7—Fe1—C9	−82.2 (4)
C11—C10—Fe1—C2	3.5 (6)	C8—C7—Fe1—C9	37.0 (3)
C9—C10—Fe1—C6	−118.5 (5)	C6—C7—Fe1—C3	81.7 (5)
C11—C10—Fe1—C6	122.2 (7)	C8—C7—Fe1—C3	−159.1 (4)
C6—C10—Fe1—C9	118.5 (5)	C6—C7—Fe1—C1	−161.0 (8)
C11—C10—Fe1—C9	−119.3 (6)	C8—C7—Fe1—C1	−41.8 (10)
C6—C10—Fe1—C3	−77.3 (5)	C6—C7—Fe1—C5	165.7 (4)
C9—C10—Fe1—C3	164.2 (5)	C8—C7—Fe1—C5	−75.1 (5)
C11—C10—Fe1—C3	45.0 (7)	C6—C7—Fe1—C4	124.8 (5)
C6—C10—Fe1—C1	−161.4 (4)	C8—C7—Fe1—C4	−116.0 (4)
C9—C10—Fe1—C1	80.1 (4)	C6—C7—Fe1—C8	−119.2 (5)
C11—C10—Fe1—C1	−39.2 (6)	C9—C8—Fe1—C2	−45.6 (10)
C6—C10—Fe1—C5	165.2 (7)	C7—C8—Fe1—C2	−165.5 (9)
C9—C10—Fe1—C5	46.7 (9)	C9—C8—Fe1—C6	82.0 (4)
C11—C10—Fe1—C5	−72.6 (9)	C7—C8—Fe1—C6	−38.0 (4)
C6—C10—Fe1—C4	−45.5 (13)	C9—C8—Fe1—C10	37.9 (3)
C9—C10—Fe1—C4	−163.9 (12)	C7—C8—Fe1—C10	−82.0 (4)
C11—C10—Fe1—C4	76.8 (13)	C7—C8—Fe1—C9	−119.9 (5)
C6—C10—Fe1—C7	37.7 (4)	C9—C8—Fe1—C3	169.9 (7)
C9—C10—Fe1—C7	−80.8 (4)	C7—C8—Fe1—C3	50.0 (9)
C11—C10—Fe1—C7	159.9 (6)	C9—C8—Fe1—C1	−75.7 (5)
C6—C10—Fe1—C8	81.7 (4)	C7—C8—Fe1—C1	164.4 (4)
C9—C10—Fe1—C8	−36.8 (3)	C9—C8—Fe1—C5	−116.8 (4)
C11—C10—Fe1—C8	−156.1 (6)	C7—C8—Fe1—C5	123.3 (4)
C8—C9—Fe1—C2	163.1 (4)	C9—C8—Fe1—C4	−157.7 (4)
C10—C9—Fe1—C2	−76.8 (5)	C7—C8—Fe1—C4	82.4 (5)
C8—C9—Fe1—C6	−81.9 (4)	C9—C8—Fe1—C7	119.9 (5)
C10—C9—Fe1—C6	38.1 (3)