Acetonitrile­dicarbon­yl(η5-penta­methyl­cyclo­penta­dien­yl)iron(II) tetra­fluorido­borate

M'thiruaine, C.M.; Friedrich, H.B.; Changamu, E.O.; Bala, M.D.

doi:10.1107/S1600536811021350

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m924

doi:10.1107/S1600536811021350

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Acetonitriledicarbonyl(η⁵-pentamethylcyclopentadienyl)iron(II) tetrafluoridoborate

Cyprian M. M'thiruaine,^a Holger B. Friedrich,^a Evans O. Changamu ^b and Muhammad D. Bala ^a ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa, and ^bChemistry Department, Kenyatta University, PO Box 43844, Nairobi, Kenya
^*Correspondence e-mail: bala@ukzn.ac.za

(Received 20 May 2011; accepted 2 June 2011; online 18 June 2011)

In the structure of the title compound, [Fe{η⁵-C₅(CH₃)₅}(NCCH₃)(CO)₂]BF₄, the arrangement of ligands around the Fe atom is in a pseudo-octahedral three-legged piano-stool fashion in which the pentamethylcyclopentadienyl (Cp*) ligand occupies three apical coordination sites, while the two carbonyl and one acetonitrile ligands form the basal axes of the coordination. The Fe—N bond length is 1.924 (3) Å and the Fe—Cp* centroid distance is 1.722 Å.

Related literature

For the synthetic route to the title compound, see: Catheline & Astruc (1984 ). For the structures of related analogues based on the (η⁵-C₅H₅) moiety, see: Callan et al. (1987 ) for acetonitrile coordination via carbon; Fadel et al. (1979 ) for acetonitrile coordination via nitrogen. For our previous work in this area, see: M'thiruaine, Friedrich, Changamu & Bala (2011 ); M'thiruaine, Friedrich, Changamu & Omondi (2011 ).

Experimental

Crystal data

[Fe(C₁₀H₁₅)(C₂H₃N)(CO)₂]BF₄
M_r = 374.95
Orthorhombic, P n a 2₁
a = 17.6211 (17) Å
b = 6.5141 (7) Å
c = 14.5794 (13) Å
V = 1673.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 173 K
0.54 × 0.34 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: integration (XPREP; Bruker, 2005 ) T_min = 0.629, T_max = 0.895
9060 measured reflections
3496 independent reflections
2941 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.120
S = 1.08
3496 reflections
214 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 13942 Friedel pairs
Flack parameter: −0.02 (3)

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811021350/hg5040sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021350/hg5040Isup2.hkl

checkCIF report

Comment top

The title compound (I) was obtained as a side product in our ongoing investigation of the reactions of substitutionally unsaturated metal complexes with nitrogen donor ligands (M'thiruaine, Friedrich, Changamu & Bala, 2011; M'thiruaine, Friedrich, Changamu & Omondi, 2011). The compound has been previously reported as the product of oxidative cleavage of the Fe—Fe bond in [η⁵-C₅(CH₃)₅Fe(CO)₂]₂ in acetonitrile and also as a product of the reaction between [η⁵-C₅(CH₃)₅Fe(CO)₂(THF)]BF₄ and acetonitrile (Catheline & Astruc 1984), but its crystal structure has not been reported. Compound (I) crystallizes in an orthorhombic Pna2₁ space group, with four discrete molecular cations and four counteranions in the unit cell. The arrangement of ligands around Fe is in a pseudo-octahedral 3-legged piano stool fashion in which the pentamethylcyclopentadienyl moiety occupies three coordination sites while the two carbonyl ligands and acetonitrile nitrogen complete the coordination. The Fe—N bond length of 1.924 (3) Å, is close to the 1.91 (1)Å reported for [η⁵-C₅H₅Fe(CO)₂(NCCH₃)]BF₄ (Fadel et al. 1979) but shorter than Fe—N bonds found in the pyrrol complex, [η⁵-C₅H₅Fe(CO)₂(C₄H₄N)] (1.962 (3) Å), and in the aminoalkane complexes, [η⁵-C₅H₅Fe(CO)₂(NH₂(CH₂)_nCH₃)]BF₄ (n=2,3) (2.017 (8), 2.013 (3) and 2.006 (2) Å) (M'thiruaine, Friedrich, Changamu & Bala, 2011) and [{η⁵-C₅H₅Fe(CO)₂}₂(µ-(NH₂CH₂CH₂NH₂)](BF₄)₂ (2.0134 (17) and 2.0085 (18) Å) (M'thiruaine, Friedrich, Changamu & Omondi, 2011). It is also interesting to note that both Fe—C (Callan et al. 1987) and Fe—N (Fadel et al. 1979) coordination of the acetonitrile (NCCH₃) molecule to Fe has been reported for Cp based complexes.

Related literature top

For the synthetic route to the title compound, see: Catheline & Astruc (1984). For the structures of related analogues based on the (η⁵-C₅H₅) moiety, see: Callan et al. (1987) for acetonitrile coordination via carbon; Fadel et al. (1979) for acetonitrile coordination via nitrogen. For our previous work in this area, see: M'thiruaine, Friedrich, Changamu & Bala (2011); M'thiruaine, Friedrich, Changamu & Omondi (2011) .

Experimental top

The title compound (I) was synthesized following the method of Catheline & Astruc (1984). Compound (I) was obtained as a yellow microcrystalline solid in an isolated yield of 92%.

Anal. Calc. for C₁₄H₁₈BF₄FeNO₂: C, 44.80; H, 4.80; N, 3.73. Found: C, 44.95; H, 4.13; N, 3.76%.

¹H-NMR (400 MHz, CDCl₃): δ 2.48 (s, 3H, NCCH₃), 1.85 (s, 15H, C₅(CH₃)₅).

¹³C-NMR (400 MHz, CDCl₃): δ 4.68 (NCCH₃) 9.54 (C₅(CH₃)₅), 99.19 (C₅(CH₃)₅), 210.08 (CO).

IR (solid state, cm^-1): ν(CO) 2044; 1992, v(CN) 2299.

Melting point = 158–160 °C.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Acetonitriledicarbonyl(η⁵-pentamethylcyclopentadienyl)iron(II) tetrafluoridoborate top

Crystal data top

[Fe(C₁₀H₁₅)(C₂H₃N)(CO)₂]BF₄	F(000) = 768
M_r = 374.95	D_x = 1.488 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3473 reflections
a = 17.6211 (17) Å	θ = 2.3–28.2°
b = 6.5141 (7) Å	µ = 0.95 mm⁻¹
c = 14.5794 (13) Å	T = 173 K
V = 1673.5 (3) Å³	Plate, yellow
Z = 4	0.54 × 0.34 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	3496 independent reflections
Radiation source: fine-focus sealed tube	2941 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 28.0°, θ_min = 2.3°
Absorption correction: integration (XPREP; Bruker, 2005)	h = −23→22
T_min = 0.629, T_max = 0.895	k = −8→6
9060 measured reflections	l = −19→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0515P)² + 1.372P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3496 reflections	Δρ_max = 0.76 e Å⁻³
214 parameters	Δρ_min = −0.39 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 13942 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (3)

Crystal data top

[Fe(C₁₀H₁₅)(C₂H₃N)(CO)₂]BF₄	V = 1673.5 (3) Å³
M_r = 374.95	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 17.6211 (17) Å	µ = 0.95 mm⁻¹
b = 6.5141 (7) Å	T = 173 K
c = 14.5794 (13) Å	0.54 × 0.34 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	3496 independent reflections
Absorption correction: integration (XPREP; Bruker, 2005)	2941 reflections with I > 2σ(I)
T_min = 0.629, T_max = 0.895	R_int = 0.044
9060 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.120	Δρ_max = 0.76 e Å⁻³
S = 1.08	Δρ_min = −0.39 e Å⁻³
3496 reflections	Absolute structure: Flack (1983), 13942 Friedel pairs
214 parameters	Absolute structure parameter: −0.02 (3)
1 restraint

Special details top

Experimental. Face indexed absorption corrections carried out with XPREP (Bruker 2005).

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	0.09216 (16)	0.7960 (5)	0.3098 (3)	0.0239 (6)
C2	0.02658 (19)	0.8041 (6)	0.3681 (3)	0.0262 (8)
C3	−0.03861 (16)	0.7629 (5)	0.3117 (4)	0.0257 (6)
C4	−0.0122 (2)	0.7201 (6)	0.2209 (3)	0.0260 (8)
C5	0.0690 (2)	0.7432 (6)	0.2201 (3)	0.0254 (7)
C6	0.1726 (2)	0.8390 (7)	0.3396 (3)	0.0400 (11)
H6A	0.2067	0.7375	0.3121	0.060*
H6B	0.1759	0.8306	0.4066	0.060*
H6C	0.1873	0.9769	0.3195	0.060*
C7	0.0265 (3)	0.8621 (8)	0.4661 (3)	0.0427 (11)
H7A	0.0329	1.0111	0.4716	0.064*
H7B	0.0684	0.7925	0.4975	0.064*
H7C	−0.0217	0.8214	0.4940	0.064*
C8	−0.1200 (2)	0.7710 (7)	0.3400 (3)	0.0426 (12)
H8A	−0.1402	0.9086	0.3282	0.064*
H8B	−0.1241	0.7400	0.4056	0.064*
H8C	−0.1491	0.6698	0.3048	0.064*
C9	−0.0613 (3)	0.6839 (7)	0.1391 (3)	0.0379 (10)
H9A	−0.0798	0.8157	0.1156	0.057*
H9B	−0.1046	0.5978	0.1566	0.057*
H9C	−0.0318	0.6143	0.0913	0.057*
C10	0.1205 (3)	0.7291 (7)	0.1393 (3)	0.0405 (11)
H10A	0.1273	0.8659	0.1126	0.061*
H10B	0.0982	0.6371	0.0934	0.061*
H10C	0.1698	0.6750	0.1588	0.061*
C11	−0.0393 (2)	0.3667 (7)	0.3676 (3)	0.0331 (9)
C12	0.0500 (2)	0.3192 (6)	0.2248 (3)	0.0335 (9)
C13	0.1669 (2)	0.3605 (6)	0.4320 (3)	0.0284 (8)
C14	0.2331 (2)	0.3052 (8)	0.4861 (4)	0.0452 (12)
H14A	0.2780	0.3025	0.4465	0.068*
H14B	0.2255	0.1692	0.5133	0.068*
H14C	0.2404	0.4065	0.5350	0.068*
B1	0.2910 (3)	0.2863 (8)	0.1717 (4)	0.0432 (13)
N1	0.11513 (17)	0.4097 (5)	0.3903 (2)	0.0265 (7)
O1	−0.08715 (17)	0.2810 (5)	0.4027 (3)	0.0530 (9)
O2	0.0583 (3)	0.2069 (5)	0.1657 (3)	0.0575 (10)
F1	0.2517 (3)	0.3976 (10)	0.2318 (4)	0.126 (2)
F2	0.2748 (3)	0.0894 (7)	0.1790 (5)	0.1188 (19)
F3	0.3707 (2)	0.3066 (8)	0.1896 (4)	0.1167 (19)
F4	0.2819 (4)	0.3427 (15)	0.0873 (5)	0.189 (4)
Fe1	0.03492 (2)	0.50825 (7)	0.31236 (7)	0.02001 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0235 (13)	0.0212 (14)	0.0270 (16)	−0.0015 (11)	−0.0006 (18)	0.002 (2)
C2	0.0246 (16)	0.0246 (18)	0.029 (2)	0.0019 (14)	0.0012 (14)	−0.0014 (16)
C3	0.0218 (13)	0.0250 (14)	0.0302 (17)	0.0031 (11)	0.0037 (17)	0.004 (2)
C4	0.0314 (17)	0.0213 (18)	0.0254 (19)	0.0015 (14)	−0.0026 (15)	0.0044 (15)
C5	0.0299 (17)	0.0209 (17)	0.0255 (19)	0.0003 (14)	0.0035 (15)	0.0024 (15)
C6	0.0243 (16)	0.034 (2)	0.061 (3)	−0.0084 (16)	−0.0037 (16)	0.001 (2)
C7	0.058 (3)	0.043 (3)	0.026 (2)	0.009 (2)	0.0010 (19)	−0.007 (2)
C8	0.0250 (17)	0.044 (2)	0.059 (3)	0.0083 (16)	0.0072 (17)	0.008 (2)
C9	0.045 (2)	0.035 (2)	0.034 (2)	−0.0034 (19)	−0.0151 (19)	0.0082 (19)
C10	0.046 (2)	0.039 (2)	0.037 (2)	0.0038 (19)	0.0203 (19)	0.007 (2)
C11	0.0275 (17)	0.030 (2)	0.042 (3)	−0.0028 (15)	−0.0055 (16)	0.0076 (19)
C12	0.044 (2)	0.028 (2)	0.028 (2)	0.0049 (17)	−0.0081 (17)	0.0039 (18)
C13	0.0223 (16)	0.033 (2)	0.030 (2)	0.0013 (15)	−0.0033 (14)	0.0001 (17)
C14	0.032 (2)	0.055 (3)	0.049 (3)	0.015 (2)	−0.0176 (19)	−0.002 (2)
B1	0.056 (3)	0.032 (3)	0.042 (3)	0.009 (2)	0.013 (2)	0.002 (2)
N1	0.0285 (15)	0.0268 (16)	0.0242 (17)	0.0001 (13)	0.0015 (12)	0.0015 (13)
O1	0.0375 (16)	0.052 (2)	0.069 (2)	−0.0149 (15)	0.0089 (17)	0.0209 (19)
O2	0.096 (3)	0.0380 (19)	0.038 (2)	0.0189 (19)	−0.0112 (19)	−0.0144 (17)
F1	0.094 (3)	0.146 (4)	0.137 (5)	0.048 (3)	−0.003 (3)	−0.081 (4)
F2	0.100 (3)	0.068 (3)	0.188 (6)	−0.008 (3)	0.037 (3)	0.015 (4)
F3	0.067 (2)	0.107 (4)	0.175 (5)	0.009 (2)	0.000 (3)	−0.041 (4)
F4	0.192 (7)	0.256 (9)	0.120 (6)	0.030 (6)	0.020 (5)	0.109 (6)
Fe1	0.01998 (19)	0.0212 (2)	0.0188 (2)	−0.00051 (17)	−0.0013 (3)	0.0014 (2)

Geometric parameters (Å, º) top

C1—C5	1.413 (6)	C8—H8B	0.9800
C1—C2	1.436 (5)	C8—H8C	0.9800
C1—C6	1.508 (5)	C9—H9A	0.9800
C1—Fe1	2.129 (3)	C9—H9B	0.9800
C2—C3	1.438 (5)	C9—H9C	0.9800
C2—C7	1.477 (6)	C10—H10A	0.9800
C2—Fe1	2.097 (4)	C10—H10B	0.9800
C3—C4	1.431 (7)	C10—H10C	0.9800
C3—C8	1.493 (5)	C11—O1	1.134 (5)
C3—Fe1	2.105 (3)	C11—Fe1	1.791 (4)
C4—C5	1.439 (5)	C12—O2	1.140 (6)
C4—C9	1.493 (6)	C12—Fe1	1.793 (5)
C4—Fe1	2.091 (4)	C13—N1	1.143 (5)
C5—C10	1.490 (5)	C13—C14	1.453 (5)
C5—Fe1	2.124 (4)	C14—H14A	0.9800
C6—H6A	0.9800	C14—H14B	0.9800
C6—H6B	0.9800	C14—H14C	0.9800
C6—H6C	0.9800	B1—F4	1.295 (9)
C7—H7A	0.9800	B1—F2	1.318 (7)
C7—H7B	0.9800	B1—F1	1.332 (7)
C7—H7C	0.9800	B1—F3	1.433 (7)
C8—H8A	0.9800	N1—Fe1	1.924 (3)

C5—C1—C2	108.9 (3)	H9A—C9—H9C	109.5
C5—C1—C6	125.7 (4)	H9B—C9—H9C	109.5
C2—C1—C6	125.4 (4)	C5—C10—H10A	109.5
C5—C1—Fe1	70.4 (2)	C5—C10—H10B	109.5
C2—C1—Fe1	68.9 (2)	H10A—C10—H10B	109.5
C6—C1—Fe1	127.1 (3)	C5—C10—H10C	109.5
C1—C2—C3	107.3 (4)	H10A—C10—H10C	109.5
C1—C2—C7	125.6 (4)	H10B—C10—H10C	109.5
C3—C2—C7	126.9 (4)	O1—C11—Fe1	178.5 (4)
C1—C2—Fe1	71.4 (2)	O2—C12—Fe1	176.2 (4)
C3—C2—Fe1	70.3 (2)	N1—C13—C14	178.0 (5)
C7—C2—Fe1	127.6 (3)	C13—C14—H14A	109.5
C4—C3—C2	107.8 (3)	C13—C14—H14B	109.5
C4—C3—C8	125.1 (4)	H14A—C14—H14B	109.5
C2—C3—C8	127.0 (5)	C13—C14—H14C	109.5
C4—C3—Fe1	69.5 (2)	H14A—C14—H14C	109.5
C2—C3—Fe1	69.69 (19)	H14B—C14—H14C	109.5
C8—C3—Fe1	128.2 (3)	F4—B1—F2	109.0 (7)
C3—C4—C5	108.1 (3)	F4—B1—F1	113.9 (6)
C3—C4—C9	125.6 (4)	F2—B1—F1	111.4 (6)
C5—C4—C9	125.9 (4)	F4—B1—F3	105.6 (6)
C3—C4—Fe1	70.6 (2)	F2—B1—F3	106.7 (5)
C5—C4—Fe1	71.3 (2)	F1—B1—F3	109.9 (5)
C9—C4—Fe1	129.5 (3)	C13—N1—Fe1	174.2 (3)
C1—C5—C4	107.8 (3)	C11—Fe1—C12	94.3 (2)
C1—C5—C10	124.8 (4)	C11—Fe1—N1	95.67 (17)
C4—C5—C10	127.3 (4)	C12—Fe1—N1	94.73 (16)
C1—C5—Fe1	70.8 (2)	C11—Fe1—C4	109.68 (17)
C4—C5—Fe1	68.8 (2)	C12—Fe1—C4	93.34 (18)
C10—C5—Fe1	128.9 (3)	N1—Fe1—C4	152.70 (14)
C1—C6—H6A	109.5	C11—Fe1—C2	104.35 (18)
C1—C6—H6B	109.5	C12—Fe1—C2	156.57 (19)
H6A—C6—H6B	109.5	N1—Fe1—C2	97.42 (15)
C1—C6—H6C	109.5	C4—Fe1—C2	67.22 (16)
H6A—C6—H6C	109.5	C11—Fe1—C3	87.62 (17)
H6B—C6—H6C	109.5	C12—Fe1—C3	129.0 (2)
C2—C7—H7A	109.5	N1—Fe1—C3	135.88 (18)
C2—C7—H7B	109.5	C4—Fe1—C3	39.87 (19)
H7A—C7—H7B	109.5	C2—Fe1—C3	40.03 (15)
C2—C7—H7C	109.5	C11—Fe1—C5	149.54 (17)
H7A—C7—H7C	109.5	C12—Fe1—C5	90.14 (18)
H7B—C7—H7C	109.5	N1—Fe1—C5	114.01 (14)
C3—C8—H8A	109.5	C4—Fe1—C5	39.90 (15)
C3—C8—H8B	109.5	C2—Fe1—C5	66.62 (15)
H8A—C8—H8B	109.5	C3—Fe1—C5	66.63 (16)
C3—C8—H8C	109.5	C11—Fe1—C1	143.80 (19)
H8A—C8—H8C	109.5	C12—Fe1—C1	121.48 (19)
H8B—C8—H8C	109.5	N1—Fe1—C1	87.48 (14)
C4—C9—H9A	109.5	C4—Fe1—C1	66.16 (15)
C4—C9—H9B	109.5	C2—Fe1—C1	39.71 (14)
H9A—C9—H9B	109.5	C3—Fe1—C1	66.28 (12)
C4—C9—H9C	109.5	C5—Fe1—C1	38.80 (17)

C5—C1—C2—C3	−2.2 (4)	C1—C2—Fe1—C4	−79.6 (2)
C6—C1—C2—C3	177.2 (3)	C3—C2—Fe1—C4	37.4 (2)
Fe1—C1—C2—C3	−61.4 (2)	C7—C2—Fe1—C4	159.4 (4)
C5—C1—C2—C7	−177.4 (4)	C1—C2—Fe1—C3	−117.0 (4)
C6—C1—C2—C7	2.1 (6)	C7—C2—Fe1—C3	121.9 (5)
Fe1—C1—C2—C7	123.4 (4)	C1—C2—Fe1—C5	−36.1 (2)
C5—C1—C2—Fe1	59.2 (2)	C3—C2—Fe1—C5	81.0 (3)
C6—C1—C2—Fe1	−121.3 (4)	C7—C2—Fe1—C5	−157.1 (4)
C1—C2—C3—C4	2.8 (4)	C3—C2—Fe1—C1	117.0 (4)
C7—C2—C3—C4	177.9 (4)	C7—C2—Fe1—C1	−121.0 (4)
Fe1—C2—C3—C4	−59.3 (2)	C4—C3—Fe1—C11	−125.1 (3)
C1—C2—C3—C8	−174.8 (3)	C2—C3—Fe1—C11	115.8 (3)
C7—C2—C3—C8	0.3 (7)	C8—C3—Fe1—C11	−5.9 (5)
Fe1—C2—C3—C8	123.1 (4)	C4—C3—Fe1—C12	−31.6 (3)
C1—C2—C3—Fe1	62.1 (3)	C2—C3—Fe1—C12	−150.7 (3)
C7—C2—C3—Fe1	−122.8 (4)	C8—C3—Fe1—C12	87.6 (5)
C2—C3—C4—C5	−2.4 (4)	C4—C3—Fe1—N1	139.2 (2)
C8—C3—C4—C5	175.3 (3)	C2—C3—Fe1—N1	20.1 (3)
Fe1—C3—C4—C5	−61.8 (2)	C8—C3—Fe1—N1	−101.6 (4)
C2—C3—C4—C9	−175.4 (4)	C2—C3—Fe1—C4	−119.1 (3)
C8—C3—C4—C9	2.3 (6)	C8—C3—Fe1—C4	119.2 (5)
Fe1—C3—C4—C9	125.2 (4)	C4—C3—Fe1—C2	119.1 (3)
C2—C3—C4—Fe1	59.4 (2)	C8—C3—Fe1—C2	−121.7 (6)
C8—C3—C4—Fe1	−122.9 (4)	C4—C3—Fe1—C5	38.2 (2)
C2—C1—C5—C4	0.8 (4)	C2—C3—Fe1—C5	−80.9 (2)
C6—C1—C5—C4	−178.7 (3)	C8—C3—Fe1—C5	157.3 (5)
Fe1—C1—C5—C4	59.1 (2)	C4—C3—Fe1—C1	80.6 (2)
C2—C1—C5—C10	177.1 (4)	C2—C3—Fe1—C1	−38.4 (2)
C6—C1—C5—C10	−2.4 (6)	C8—C3—Fe1—C1	−160.2 (5)
Fe1—C1—C5—C10	−124.6 (4)	C1—C5—Fe1—C11	115.2 (4)
C2—C1—C5—Fe1	−58.3 (3)	C4—C5—Fe1—C11	−3.6 (5)
C6—C1—C5—Fe1	122.2 (3)	C10—C5—Fe1—C11	−125.1 (5)
C3—C4—C5—C1	1.0 (4)	C1—C5—Fe1—C12	−146.1 (2)
C9—C4—C5—C1	174.0 (4)	C4—C5—Fe1—C12	95.0 (2)
Fe1—C4—C5—C1	−60.3 (3)	C10—C5—Fe1—C12	−26.4 (4)
C3—C4—C5—C10	−175.2 (4)	C1—C5—Fe1—N1	−50.9 (2)
C9—C4—C5—C10	−2.2 (7)	C4—C5—Fe1—N1	−169.7 (2)
Fe1—C4—C5—C10	123.5 (4)	C10—C5—Fe1—N1	68.8 (4)
C3—C4—C5—Fe1	61.3 (2)	C1—C5—Fe1—C4	118.8 (3)
C9—C4—C5—Fe1	−125.7 (4)	C10—C5—Fe1—C4	−121.5 (5)
C3—C4—Fe1—C11	60.2 (3)	C1—C5—Fe1—C2	36.89 (19)
C5—C4—Fe1—C11	178.1 (2)	C4—C5—Fe1—C2	−81.9 (2)
C9—C4—Fe1—C11	−60.4 (4)	C10—C5—Fe1—C2	156.6 (4)
C3—C4—Fe1—C12	155.9 (2)	C1—C5—Fe1—C3	80.7 (2)
C5—C4—Fe1—C12	−86.2 (3)	C4—C5—Fe1—C3	−38.1 (2)
C9—C4—Fe1—C12	35.3 (4)	C10—C5—Fe1—C3	−159.6 (4)
C3—C4—Fe1—N1	−97.0 (4)	C4—C5—Fe1—C1	−118.8 (3)
C5—C4—Fe1—N1	20.8 (4)	C10—C5—Fe1—C1	119.7 (5)
C9—C4—Fe1—N1	142.4 (4)	C5—C1—Fe1—C11	−129.0 (3)
C3—C4—Fe1—C2	−37.6 (2)	C2—C1—Fe1—C11	−8.6 (4)
C5—C4—Fe1—C2	80.3 (2)	C6—C1—Fe1—C11	110.5 (4)
C9—C4—Fe1—C2	−158.2 (4)	C5—C1—Fe1—C12	40.8 (3)
C5—C4—Fe1—C3	117.9 (3)	C2—C1—Fe1—C12	161.2 (2)
C9—C4—Fe1—C3	−120.6 (5)	C6—C1—Fe1—C12	−79.7 (5)
C3—C4—Fe1—C5	−117.9 (3)	C5—C1—Fe1—N1	134.8 (2)
C9—C4—Fe1—C5	121.6 (5)	C2—C1—Fe1—N1	−104.8 (2)
C3—C4—Fe1—C1	−81.0 (2)	C6—C1—Fe1—N1	14.3 (4)
C5—C4—Fe1—C1	36.9 (2)	C5—C1—Fe1—C4	−37.9 (2)
C9—C4—Fe1—C1	158.4 (4)	C2—C1—Fe1—C4	82.5 (2)
C1—C2—Fe1—C11	174.8 (2)	C6—C1—Fe1—C4	−158.4 (5)
C3—C2—Fe1—C11	−68.2 (3)	C5—C1—Fe1—C2	−120.4 (3)
C7—C2—Fe1—C11	53.7 (4)	C6—C1—Fe1—C2	119.1 (5)
C1—C2—Fe1—C12	−43.7 (5)	C5—C1—Fe1—C3	−81.7 (3)
C3—C2—Fe1—C12	73.3 (5)	C2—C1—Fe1—C3	38.7 (3)
C7—C2—Fe1—C12	−164.7 (4)	C6—C1—Fe1—C3	157.9 (5)
C1—C2—Fe1—N1	76.9 (2)	C2—C1—Fe1—C5	120.4 (3)
C3—C2—Fe1—N1	−166.0 (2)	C6—C1—Fe1—C5	−120.5 (5)
C7—C2—Fe1—N1	−44.1 (4)

Experimental details

Crystal data
Chemical formula	[Fe(C₁₀H₁₅)(C₂H₃N)(CO)₂]BF₄
M_r	374.95
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	17.6211 (17), 6.5141 (7), 14.5794 (13)
V (Å³)	1673.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.54 × 0.34 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Integration (XPREP; Bruker, 2005)
T_min, T_max	0.629, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	9060, 3496, 2941
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.120, 1.08
No. of reflections	3496
No. of parameters	214
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.39
Absolute structure	Flack (1983), 13942 Friedel pairs
Absolute structure parameter	−0.02 (3)

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Acknowledgements

We wish to thank Dr Manuel Fernandes (University of the Witwatersrand) for data collection, solution and refinement. Our acknowledgement also goes to the NRF and the University of KwaZulu-Natal for resources and financial support.

References

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