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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 18;67(Pt 7):m924. doi: 10.1107/S1600536811021350

Acetonitrile­dicarbon­yl(η5-penta­methyl­cyclo­penta­dien­yl)iron(II) tetra­fluorido­borate

Cyprian M M’thiruaine a, Holger B Friedrich a, Evans O Changamu b, Muhammad D Bala a,*
PMCID: PMC3151746  PMID: 21836908

Abstract

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 ▶). graphic file with name e-67-0m924-scheme1.jpg

Experimental

Crystal data

  • [Fe(C10H15)(C2H3N)(CO)2]BF4

  • M r = 374.95

  • Orthorhombic, Inline graphic

  • 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[F 2 > 2σ(F 2)] = 0.044

  • wR(F 2) = 0.120

  • S = 1.08

  • 3496 reflections

  • 214 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.76 e Å−3

  • Δρmin = −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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021350/hg5040sup1.cif

e-67-0m924-sup1.cif (23.4KB, cif)

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

e-67-0m924-Isup2.hkl (168KB, hkl)

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H-atoms were refined using a riding model, with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

Fig. 1.

Fig. 1.

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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.

Crystal data

[Fe(C10H15)(C2H3N)(CO)2]BF4 F(000) = 768
Mr = 374.95 Dx = 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
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Data collection

Bruker APEXII CCD diffractometer 3496 independent reflections
Radiation source: fine-focus sealed tube 2941 reflections with I > 2σ(I)
graphite Rint = 0.044
φ and ω scans θmax = 28.0°, θmin = 2.3°
Absorption correction: integration (XPREP; Bruker, 2005) h = −23→22
Tmin = 0.629, Tmax = 0.895 k = −8→6
9060 measured reflections l = −19→12
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Refinement

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(Fo2) + (0.0515P)2 + 1.372P] where P = (Fo2 + 2Fc2)/3
S = 1.08 (Δ/σ)max = 0.001
3496 reflections Δρmax = 0.76 e Å−3
214 parameters Δρmin = −0.39 e Å−3
1 restraint Absolute structure: Flack (1983), 13942 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: −0.02 (3)
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
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)
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5040).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021350/hg5040sup1.cif

e-67-0m924-sup1.cif (23.4KB, cif)

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

e-67-0m924-Isup2.hkl (168KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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