1-(Ferrocen-1-ylmeth­yl)-3-methyl­imidazol-3-ium iodide

Nyamori, V.O.; Zulu, S.M.; Omondi, B.

doi:10.1107/S1600536812045400

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1469

doi:10.1107/S1600536812045400

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1-(Ferrocen-1-ylmethyl)-3-methylimidazol-3-ium iodide

Vincent O. Nyamori,^a Siphesihle M. Zulu ^a and Bernard Omondi ^a ^*

^aSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: owaga@ukzn.ac.za

(Received 4 October 2012; accepted 2 November 2012; online 10 November 2012)

The structure of the title compound, [Fe(C₅H₅)(C₁₀H₁₂N₂)]I, consists of a 1-(ferrocen-1-ylmethyl)-3-methylimidazolium cation which is counter-balanced by an iodide anion. The cyclopentadienyl (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 interplanar 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_r = 408.06
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.134
S = 1.20
2972 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 2.51 e Å⁻³
Δρ_min = −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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812045400/hg5258sup1.cif

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

checkCIF report

Comment top

The versatility of ferrocene has seen it be derivatized into a variety of compounds. Because of its stability and unique electronic and redox properties, ferrocene and its derivatives have been successfully applied with much success in various fields including medicinal chemistry (Ornelas, 2011, Simenel et al., 2003). Ferrocenyl imidazolium salts are a special class of ferrocene derivatives which have a cationic ferrocene-imidazole moiety [FcIm⁺] balanced by an inorganic anion X^-. These compounds can be applied as ionic liquids (Taylor & Licence, 2012; Gao et al., 2004) and as precursors to ferrocenated imidazolium carbenes (Coleman et al., 2005). The title compound was synthesized via solvent-free conditions providing an economical and clean product requiring less tidious purification process similar to reactions by Bala and Coville (2007) in which one of the reagents is a liquid and acts as a solvating medium.

The average bond lengths between the iron atom (Fe1) and the centroids of the substituted Cp ring (C6–C10) and the unsubstituted Cp ring (C1–C5) are 2.0382 (6) and 2.0354(7.4). The cyclopentadienyl rings of the ferrocene moiety have a slightly staggered conformation. The staggering angle between the two rings is 3.5 (6)° which is smaller than that of Nyamori & Bala (2008), Nyamori et al., (2010) and Nyamori et al., (2012)

Related literature top

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 et al. (2012).

Experimental top

In a round bottom flask, methyl iodide (1.64 ml, 3.75 g, 26.4 mmol) was added to 1-Ferrocenylmethyl-1H-imidazole (2.00 g, 7.50 mmol) and allowed to reflux for 12 hrs, at 50 °C under innert atmosphere. The reaction mixture was then allowed to cool to room temperature and washed with anhydrous diethylether (3 x 10 ml). A yellow solid was obtained, which was further dried invacuo. Yellow crystals crystals were obtained from recrystallization in diethylether (2.78 g, 91%); m.p. 134–136 °C (lit. 130–135 °C); IR (ATR cm-1) 3430, 3042, 1567, 1549, 1429, 1150, 1040, 837, 820, 755, 620, 500, 482; ¹H NMR (CDCl₃) 10.13 (1H, s, NCH), 7.16 (2H, m, NCH), 5.38 (1H, q, CH), 4.43 (2H, t, C₅H₄), 4.32 (2H, t, C₅H₄), 4.29 (5H, s, C₅H₅), 4.06 (3H, s, NCH₃); ¹³C NMR (CDCl₃) 136.12, 123.63, 121.91, 78.83, 70.09, 69.46, 50.12, 37.15; m/z (ESI) [M+] - I 281. (100%), 199 (60%); Anal. Calc. for C₁₅H₁₇N₂Fe⁺ 281.07411.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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).

Figures top

Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.

1-(Ferrocen-1-ylmethyl)-3-methylimidazol-3-ium iodide top

Crystal data top

[Fe(C₅H₅)(C₁₀H₁₂N₂)]I	F(000) = 800
M_r = 408.06	D_x = 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

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2745 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.042
ω scans	θ_max = 74°, θ_min = 4.0°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions of Clark & Reid (1995)]	h = −6→8
T_min = 0.114, T_max = 0.285	k = −10→11
6978 measured reflections	l = −19→27
2972 independent reflections

Refinement top

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(F_o²) + (0.0682P)² + 3.7636P] where P = (F_o² + 2F_c²)/3
2972 reflections	(Δ/σ)_max = 0.011
173 parameters	Δρ_max = 2.51 e Å⁻³
0 restraints	Δρ_min = −1.53 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₀H₁₂N₂)]I	V = 1509.39 (10) Å³
M_r = 408.06	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 7.2745 (3) Å	µ = 23.96 mm⁻¹
b = 9.3164 (3) Å	T = 173 K
c = 22.2744 (9) Å	0.16 × 0.12 × 0.07 mm
β = 90.927 (3)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2972 independent reflections
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions of Clark & Reid (1995)]	2745 reflections with I > 2σ(I)
T_min = 0.114, T_max = 0.285	R_int = 0.042
6978 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.20	Δρ_max = 2.51 e Å⁻³
2972 reflections	Δρ_min = −1.53 e Å⁻³
173 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₀H₁₂N₂)]I
M_r	408.06
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.2745 (3), 9.3164 (3), 22.2744 (9)
β (°)	90.927 (3)
V (Å³)	1509.39 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	23.96
Crystal size (mm)	0.16 × 0.12 × 0.07

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction	Analytical [CrysAlis PRO (Agilent, 2012), based on expressions of Clark & Reid (1995)]
T_min, T_max	0.114, 0.285
No. of measured, independent and observed [I > 2σ(I)] reflections	6978, 2972, 2745
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.134, 1.20
No. of reflections	2972
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.51, −1.53

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), WinGX (Farrugia, 2012).

Acknowledgements

We thank the University of KwaZulu-Natal and the National Research Foundation (NRF) for financial support. We also thank Alex Griffin from Agilent Technology XRD for the data collection and structure solution.

References

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