Literature DB >> 22589753

1-(Ferrocen-1-ylmeth-yl)-3-methyl-imidazol-3-ium hexa-fluorido-phosphate.

Vincent O Nyamori1, Siphesihle M Zulu, Bernard Omondi.   

Abstract

The crystal structure of the title compound, [Fe(C(5)H(5))(C(10)H(12)N(2))]PF(6), consists of a ferrocene-1-methyl-(3-methyl-imidazolium) cation and a hexa-fluorido-phosphate anion. The ferrocenyl rings are skewed by 6.7 (4)° from the ideal eclipsed conformation. The inter-planar angle between the plane of the substituted cyclo-penta-dienyl ring and that of the imidazole ring is 89.9 (4)°. The crystal packing is stabilized by C-H⋯F hydrogen bonds.

Entities:  

Year:  2012        PMID： 22589753      PMCID： PMC3343779          DOI： 10.1107/S1600536812008719

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to the chemistry of ferrocenes and their potential applications, see: Štěpnička (2008 ▶), Kealy & Pauson (1951 ▶); Togni & Hayashi (1995 ▶). For related work based on ferrocenylimidazolium salts, see: Nyamori et al. (2010a ▶); Thomas et al. (2000 ▶, 2002 ▶). For the synthesis, see: Nyamori et al. (2010b ▶). For related structures, see Nyamori & Bala (2008 ▶); Nyamori et al. (2010a ▶).

Experimental

Crystal data

[Fe(C5H5)(C10H12N2)]PF6 M = 426.13 Orthorhombic, a = 12.4226 (2) Å b = 13.4414 (2) Å c = 19.2137 (3) Å V = 3208.25 (9) Å3 Z = 8 Mo Kα radiation μ = 1.11 mm−1 T = 100 K 0.27 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.755, T max = 0.888 44208 measured reflections 4041 independent reflections 3747 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.064 S = 1.04 4041 reflections 227 parameters H-atom parameters constrained Δρmax = 0.46 e Å−3 Δρmin = −0.36 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008719/fj2522sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008719/fj2522Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Fe(C5H5)(C10H12N2)]PF6F(000) = 1728
Mr = 426.13Dx = 1.764 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 47745 reflections
a = 12.4226 (2) Åθ = 2.1–28.6°
b = 13.4414 (2) ŵ = 1.11 mm−1
c = 19.2137 (3) ÅT = 100 K
V = 3208.25 (9) Å3Block, yellow
Z = 80.27 × 0.17 × 0.11 mm
Bruker SMART APEXII CCD diffractometer3747 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 28.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −16→16
Tmin = 0.755, Tmax = 0.888k = −18→17
44208 measured reflectionsl = −25→25
4041 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0307P)2 + 2.2775P] where P = (Fo2 + 2Fc2)/3
4041 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.98 Å for Me H atoms, 0.99 Å for Methylene H atoms, 0.99 for methine H atoms and 0.95 Å for aromatic H atoms; Uiso(H) = 1.2Ueq(C) (1.5 for Me groups)] and were included in the refinement in the riding model approximation. The N—H H-atom was located in a difference map and freely refined with N—H = 0.88 Å (Uiso(H) = 1.2Ueq(N).
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. The following ALERTS were generated. Each ALERT has the format test-name_ALERT_alert-type_alert-level. PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of P1 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 62 PLAT960_ALERT_3_G Number of Intensities with I. LT. - 2*sig(I) ··· 4 Noted:
xyzUiso*/Ueq
C10.70208 (10)0.06956 (9)0.08674 (7)0.0187 (2)
H10.69180.06770.13830.022*
C20.63898 (10)0.01756 (9)0.03683 (7)0.0190 (2)
H20.5772−0.02780.04710.023*
C30.67965 (11)0.04158 (10)−0.03054 (7)0.0216 (3)
H30.65150.0158−0.07580.026*
C40.76762 (11)0.10892 (10)−0.02199 (7)0.0219 (3)
H40.81180.1387−0.06020.026*
C50.78092 (10)0.12621 (10)0.05054 (7)0.0203 (3)
H50.83590.17080.07230.024*
C60.50453 (10)0.22435 (9)−0.03703 (7)0.0163 (2)
H60.47070.1933−0.0790.02*
C70.47250 (10)0.20950 (9)0.03352 (7)0.0183 (2)
H70.41270.16540.04970.022*
C80.54191 (11)0.26670 (9)0.07702 (7)0.0189 (2)
H80.53920.26970.1290.023*
C90.61633 (11)0.31834 (9)0.03367 (7)0.0168 (2)
H90.67480.3640.04980.02*
C100.59352 (10)0.29181 (9)−0.03694 (6)0.0144 (2)
C110.65066 (11)0.32967 (9)−0.10021 (7)0.0178 (2)
H11A0.71490.3681−0.08590.021*
H11B0.6750.2728−0.12890.021*
C120.55414 (10)0.37912 (9)−0.20841 (6)0.0165 (2)
H120.58250.328−0.23720.02*
C130.52134 (10)0.47496 (9)−0.11803 (7)0.0174 (2)
H130.52340.502−0.07240.021*
C140.46165 (10)0.50875 (9)−0.17209 (7)0.0174 (2)
H140.41390.5639−0.17160.021*
C150.43846 (11)0.45908 (10)−0.29794 (7)0.0213 (3)
H15A0.46630.5202−0.31910.032*
H15B0.35980.4628−0.2950.032*
H15C0.45910.4018−0.32650.032*
N10.57853 (8)0.39380 (8)−0.14182 (5)0.0149 (2)
N20.48347 (9)0.44783 (8)−0.22797 (5)0.0152 (2)
F10.68267 (7)0.32029 (6)0.25538 (6)0.0312 (2)
F20.83765 (8)0.29514 (8)0.31564 (5)0.0337 (2)
F30.78054 (9)0.34815 (8)0.15824 (5)0.0390 (2)
F40.93499 (7)0.32338 (7)0.21887 (5)0.0332 (2)
F50.80333 (8)0.20561 (7)0.21913 (5)0.0346 (2)
F60.81291 (7)0.43793 (6)0.25467 (5)0.0303 (2)
Fe10.629560 (14)0.167551 (12)0.019064 (9)0.01225 (6)
P10.80910 (3)0.32180 (2)0.236862 (17)0.01482 (8)
U11U22U33U12U13U23
C10.0200 (6)0.0167 (6)0.0193 (6)0.0016 (5)−0.0043 (5)0.0048 (5)
C20.0192 (6)0.0114 (5)0.0265 (6)0.0006 (4)−0.0035 (5)0.0019 (5)
C30.0267 (7)0.0166 (6)0.0216 (6)0.0081 (5)−0.0035 (5)−0.0036 (5)
C40.0201 (6)0.0204 (6)0.0252 (7)0.0075 (5)0.0046 (5)0.0053 (5)
C50.0140 (5)0.0189 (6)0.0280 (7)0.0006 (5)−0.0047 (5)0.0047 (5)
C60.0148 (5)0.0145 (5)0.0196 (6)0.0021 (4)−0.0032 (4)0.0010 (5)
C70.0153 (5)0.0164 (6)0.0233 (6)0.0028 (5)0.0022 (5)0.0026 (5)
C80.0243 (6)0.0157 (5)0.0167 (6)0.0036 (5)0.0026 (5)−0.0008 (4)
C90.0211 (6)0.0120 (5)0.0172 (6)0.0009 (4)−0.0013 (5)−0.0012 (4)
C100.0157 (5)0.0120 (5)0.0155 (5)0.0026 (4)−0.0007 (4)0.0014 (4)
C110.0171 (5)0.0189 (6)0.0174 (6)0.0043 (5)0.0003 (5)0.0053 (4)
C120.0188 (6)0.0138 (5)0.0168 (6)−0.0001 (4)0.0000 (4)0.0001 (4)
C130.0209 (6)0.0155 (5)0.0159 (6)0.0027 (5)0.0016 (5)0.0002 (4)
C140.0192 (6)0.0149 (5)0.0182 (6)0.0017 (5)0.0014 (5)0.0009 (4)
C150.0263 (7)0.0217 (6)0.0158 (6)0.0013 (5)−0.0058 (5)0.0009 (5)
N10.0161 (5)0.0134 (5)0.0154 (5)0.0011 (4)0.0005 (4)0.0028 (4)
N20.0165 (5)0.0140 (5)0.0152 (5)−0.0012 (4)−0.0017 (4)0.0010 (4)
F10.0143 (4)0.0267 (4)0.0526 (6)−0.0019 (3)−0.0009 (4)0.0108 (4)
F20.0334 (5)0.0497 (6)0.0180 (4)−0.0015 (4)−0.0067 (4)0.0080 (4)
F30.0562 (6)0.0405 (5)0.0202 (4)−0.0019 (5)−0.0115 (4)0.0082 (4)
F40.0205 (4)0.0331 (5)0.0459 (6)0.0019 (4)0.0112 (4)0.0017 (4)
F50.0383 (5)0.0165 (4)0.0490 (6)0.0017 (4)−0.0128 (4)−0.0042 (4)
F60.0241 (4)0.0188 (4)0.0481 (6)−0.0028 (3)−0.0019 (4)−0.0082 (4)
Fe10.01293 (10)0.01083 (9)0.01299 (9)0.00042 (6)−0.00162 (6)0.00074 (6)
P10.01470 (15)0.01456 (14)0.01521 (15)−0.00112 (11)−0.00222 (11)0.00146 (11)
C1—C21.4222 (18)C9—Fe12.0527 (12)
C1—C51.4223 (18)C9—H91
C1—Fe12.0585 (12)C10—C111.4968 (17)
C1—H11C10—Fe12.0367 (12)
C2—C31.4267 (19)C11—N11.4782 (15)
C2—Fe12.0482 (13)C11—H11A0.99
C2—H21C11—H11B0.99
C3—C41.428 (2)C12—N21.3285 (16)
C3—Fe12.0403 (13)C12—N11.3296 (16)
C3—H31C12—H120.95
C4—C51.4225 (19)C13—C141.3547 (17)
C4—Fe12.0456 (13)C13—N11.3797 (16)
C4—H41C13—H130.95
C5—Fe12.0519 (13)C14—N21.3772 (16)
C5—H51C14—H140.95
C6—C71.4269 (18)C15—N21.4637 (16)
C6—C101.4299 (17)C15—H15A0.98
C6—Fe12.0389 (12)C15—H15B0.98
C6—H61C15—H15C0.98
C7—C81.4258 (19)F1—P11.6106 (9)
C7—Fe12.0498 (13)F2—P11.5954 (9)
C7—H71F3—P11.5917 (9)
C8—C91.4249 (18)F4—P11.6018 (9)
C8—Fe12.0497 (13)F5—P11.6001 (9)
C8—H81F6—P11.5988 (9)
C9—C101.4310 (17)
C2—C1—C5108.23 (12)N2—C14—H14126.6
C2—C1—Fe169.35 (7)N2—C15—H15A109.5
C5—C1—Fe169.50 (7)N2—C15—H15B109.5
C2—C1—H1125.9H15A—C15—H15B109.5
C5—C1—H1125.9N2—C15—H15C109.5
Fe1—C1—H1125.9H15A—C15—H15C109.5
C1—C2—C3107.78 (12)H15B—C15—H15C109.5
C1—C2—Fe170.13 (7)C12—N1—C13108.59 (10)
C3—C2—Fe169.28 (7)C12—N1—C11124.89 (11)
C1—C2—H2126.1C13—N1—C11126.45 (11)
C3—C2—H2126.1C12—N2—C14108.84 (10)
Fe1—C2—H2126.1C12—N2—C15125.74 (11)
C2—C3—C4108.06 (12)C14—N2—C15125.40 (11)
C2—C3—Fe169.87 (7)C10—Fe1—C641.08 (5)
C4—C3—Fe169.74 (8)C10—Fe1—C3120.05 (5)
C2—C3—H3126C6—Fe1—C3107.22 (5)
C4—C3—H3126C10—Fe1—C4107.24 (5)
Fe1—C3—H3126C6—Fe1—C4125.38 (5)
C5—C4—C3107.76 (12)C3—Fe1—C440.93 (6)
C5—C4—Fe169.92 (7)C10—Fe1—C2155.21 (5)
C3—C4—Fe169.34 (8)C6—Fe1—C2120.01 (5)
C5—C4—H4126.1C3—Fe1—C240.85 (5)
C3—C4—H4126.1C4—Fe1—C268.73 (5)
Fe1—C4—H4126.1C10—Fe1—C868.72 (5)
C1—C5—C4108.16 (12)C6—Fe1—C868.84 (5)
C1—C5—Fe170.01 (7)C3—Fe1—C8162.82 (6)
C4—C5—Fe169.45 (7)C4—Fe1—C8154.87 (6)
C1—C5—H5125.9C2—Fe1—C8125.44 (5)
C4—C5—H5125.9C10—Fe1—C768.70 (5)
Fe1—C5—H5125.9C6—Fe1—C740.85 (5)
C7—C6—C10107.64 (11)C3—Fe1—C7125.58 (6)
C7—C6—Fe169.99 (7)C4—Fe1—C7162.98 (6)
C10—C6—Fe169.38 (7)C2—Fe1—C7107.61 (5)
C7—C6—H6126.2C8—Fe1—C740.70 (5)
C10—C6—H6126.2C10—Fe1—C5125.40 (5)
Fe1—C6—H6126.2C6—Fe1—C5162.81 (5)
C8—C7—C6108.23 (11)C3—Fe1—C568.50 (6)
C8—C7—Fe169.65 (7)C4—Fe1—C540.63 (5)
C6—C7—Fe169.17 (7)C2—Fe1—C568.40 (5)
C8—C7—H7125.9C8—Fe1—C5120.18 (6)
C6—C7—H7125.9C7—Fe1—C5155.07 (6)
Fe1—C7—H7125.9C10—Fe1—C940.97 (5)
C9—C8—C7108.20 (11)C6—Fe1—C969.00 (5)
C9—C8—Fe169.79 (7)C3—Fe1—C9155.19 (6)
C7—C8—Fe169.65 (7)C4—Fe1—C9120.01 (6)
C9—C8—H8125.9C2—Fe1—C9162.50 (6)
C7—C8—H8125.9C8—Fe1—C940.65 (5)
Fe1—C8—H8125.9C7—Fe1—C968.51 (5)
C8—C9—C10107.72 (11)C5—Fe1—C9107.49 (5)
C8—C9—Fe169.57 (7)C10—Fe1—C1162.69 (5)
C10—C9—Fe168.92 (7)C6—Fe1—C1155.08 (5)
C8—C9—H9126.1C3—Fe1—C168.32 (5)
C10—C9—H9126.1C4—Fe1—C168.30 (5)
Fe1—C9—H9126.1C2—Fe1—C140.52 (5)
C6—C10—C9108.20 (11)C8—Fe1—C1107.78 (5)
C6—C10—C11125.54 (11)C7—Fe1—C1120.46 (5)
C9—C10—C11126.25 (11)C5—Fe1—C140.49 (5)
C6—C10—Fe169.54 (7)C9—Fe1—C1125.48 (5)
C9—C10—Fe170.12 (7)F3—P1—F2179.87 (7)
C11—C10—Fe1127.13 (9)F3—P1—F689.57 (6)
N1—C11—C10110.49 (10)F2—P1—F690.55 (6)
N1—C11—H11A109.6F3—P1—F590.29 (6)
C10—C11—H11A109.6F2—P1—F589.58 (6)
N1—C11—H11B109.6F6—P1—F5179.13 (5)
C10—C11—H11B109.6F3—P1—F490.57 (6)
H11A—C11—H11B108.1F2—P1—F489.46 (5)
N2—C12—N1108.65 (11)F6—P1—F490.25 (5)
N2—C12—H12125.7F5—P1—F490.62 (5)
N1—C12—H12125.7F3—P1—F189.71 (6)
C14—C13—N1107.04 (11)F2—P1—F190.25 (5)
C14—C13—H13126.5F6—P1—F189.65 (5)
N1—C13—H13126.5F5—P1—F189.49 (5)
C13—C14—N2106.90 (11)F4—P1—F1179.70 (6)
C13—C14—H14126.6
C5—C1—C2—C30.48 (14)C5—C4—Fe1—C3−119.01 (11)
Fe1—C1—C2—C359.27 (9)C5—C4—Fe1—C2−81.21 (8)
C5—C1—C2—Fe1−58.79 (9)C3—C4—Fe1—C237.80 (8)
C1—C2—C3—C4−0.30 (15)C5—C4—Fe1—C848.21 (15)
Fe1—C2—C3—C459.51 (9)C3—C4—Fe1—C8167.22 (11)
C1—C2—C3—Fe1−59.80 (9)C5—C4—Fe1—C7−161.85 (16)
C2—C3—C4—C50.00 (15)C3—C4—Fe1—C7−42.8 (2)
Fe1—C3—C4—C559.60 (9)C3—C4—Fe1—C5119.01 (11)
C2—C3—C4—Fe1−59.59 (9)C5—C4—Fe1—C981.93 (9)
C2—C1—C5—C4−0.48 (15)C3—C4—Fe1—C9−159.06 (8)
Fe1—C1—C5—C4−59.17 (9)C5—C4—Fe1—C1−37.51 (8)
C2—C1—C5—Fe158.70 (9)C3—C4—Fe1—C181.50 (8)
C3—C4—C5—C10.29 (15)C1—C2—Fe1—C10166.23 (11)
Fe1—C4—C5—C159.52 (9)C3—C2—Fe1—C1047.29 (15)
C3—C4—C5—Fe1−59.23 (9)C1—C2—Fe1—C6−159.41 (8)
C10—C6—C7—C8−0.54 (14)C3—C2—Fe1—C681.65 (9)
Fe1—C6—C7—C858.86 (9)C1—C2—Fe1—C3118.94 (11)
C10—C6—C7—Fe1−59.39 (8)C1—C2—Fe1—C481.07 (8)
C6—C7—C8—C90.78 (14)C3—C2—Fe1—C4−37.87 (8)
Fe1—C7—C8—C959.34 (9)C1—C2—Fe1—C8−75.18 (9)
C6—C7—C8—Fe1−58.56 (9)C3—C2—Fe1—C8165.88 (8)
C7—C8—C9—C10−0.73 (14)C1—C2—Fe1—C7−116.57 (8)
Fe1—C8—C9—C1058.53 (8)C3—C2—Fe1—C7124.49 (8)
C7—C8—C9—Fe1−59.26 (9)C1—C2—Fe1—C537.27 (8)
C7—C6—C10—C90.09 (14)C3—C2—Fe1—C5−81.67 (8)
Fe1—C6—C10—C9−59.69 (8)C1—C2—Fe1—C9−42.3 (2)
C7—C6—C10—C11−178.54 (11)C3—C2—Fe1—C9−161.25 (16)
Fe1—C6—C10—C11121.69 (12)C3—C2—Fe1—C1−118.94 (11)
C7—C6—C10—Fe159.77 (8)C9—C8—Fe1—C10−37.78 (7)
C8—C9—C10—C60.39 (14)C7—C8—Fe1—C1081.67 (8)
Fe1—C9—C10—C659.33 (8)C9—C8—Fe1—C6−82.00 (8)
C8—C9—C10—C11179.01 (11)C7—C8—Fe1—C637.45 (7)
Fe1—C9—C10—C11−122.06 (12)C9—C8—Fe1—C3−161.81 (16)
C8—C9—C10—Fe1−58.94 (9)C7—C8—Fe1—C3−42.4 (2)
C6—C10—C11—N166.58 (15)C9—C8—Fe1—C447.57 (15)
C9—C10—C11—N1−111.80 (14)C7—C8—Fe1—C4167.01 (11)
Fe1—C10—C11—N1156.70 (9)C9—C8—Fe1—C2165.49 (8)
N1—C13—C14—N2−0.09 (14)C7—C8—Fe1—C2−75.06 (9)
N2—C12—N1—C13−0.05 (14)C9—C8—Fe1—C7−119.45 (11)
N2—C12—N1—C11176.98 (11)C9—C8—Fe1—C581.73 (9)
C14—C13—N1—C120.09 (14)C7—C8—Fe1—C5−158.82 (7)
C14—C13—N1—C11−176.88 (11)C7—C8—Fe1—C9119.45 (11)
C10—C11—N1—C12−123.38 (13)C9—C8—Fe1—C1124.22 (8)
C10—C11—N1—C1353.11 (16)C7—C8—Fe1—C1−116.34 (8)
N1—C12—N2—C14−0.01 (14)C8—C7—Fe1—C10−81.71 (8)
N1—C12—N2—C15178.28 (11)C6—C7—Fe1—C1038.17 (7)
C13—C14—N2—C120.06 (14)C8—C7—Fe1—C6−119.88 (11)
C13—C14—N2—C15−178.23 (12)C8—C7—Fe1—C3165.83 (8)
C9—C10—Fe1—C6119.29 (11)C6—C7—Fe1—C3−74.28 (9)
C11—C10—Fe1—C6−119.72 (14)C8—C7—Fe1—C4−160.96 (17)
C6—C10—Fe1—C381.77 (9)C6—C7—Fe1—C4−41.1 (2)
C9—C10—Fe1—C3−158.93 (8)C8—C7—Fe1—C2124.32 (8)
C11—C10—Fe1—C3−37.94 (13)C6—C7—Fe1—C2−115.80 (8)
C6—C10—Fe1—C4124.51 (8)C6—C7—Fe1—C8119.88 (11)
C9—C10—Fe1—C4−116.19 (8)C8—C7—Fe1—C547.80 (15)
C11—C10—Fe1—C44.80 (12)C6—C7—Fe1—C5167.69 (11)
C6—C10—Fe1—C248.05 (15)C8—C7—Fe1—C9−37.56 (7)
C9—C10—Fe1—C2167.34 (12)C6—C7—Fe1—C982.32 (8)
C11—C10—Fe1—C2−71.67 (17)C8—C7—Fe1—C181.92 (9)
C6—C10—Fe1—C8−81.80 (8)C6—C7—Fe1—C1−158.19 (7)
C9—C10—Fe1—C837.50 (8)C1—C5—Fe1—C10166.27 (7)
C11—C10—Fe1—C8158.48 (13)C4—C5—Fe1—C10−74.35 (9)
C6—C10—Fe1—C7−37.97 (7)C1—C5—Fe1—C6−160.03 (16)
C9—C10—Fe1—C781.33 (8)C4—C5—Fe1—C6−40.7 (2)
C11—C10—Fe1—C7−157.68 (12)C1—C5—Fe1—C3−81.37 (8)
C6—C10—Fe1—C5165.55 (8)C4—C5—Fe1—C338.01 (8)
C9—C10—Fe1—C5−75.16 (9)C1—C5—Fe1—C4−119.38 (11)
C11—C10—Fe1—C545.83 (13)C1—C5—Fe1—C2−37.30 (8)
C6—C10—Fe1—C9−119.29 (11)C4—C5—Fe1—C282.08 (9)
C11—C10—Fe1—C9120.99 (14)C1—C5—Fe1—C882.11 (9)
C6—C10—Fe1—C1−163.26 (16)C4—C5—Fe1—C8−158.51 (8)
C9—C10—Fe1—C1−44.0 (2)C1—C5—Fe1—C748.13 (16)
C11—C10—Fe1—C177.0 (2)C4—C5—Fe1—C7167.51 (11)
C7—C6—Fe1—C10−118.80 (10)C1—C5—Fe1—C9124.63 (8)
C7—C6—Fe1—C3124.95 (8)C4—C5—Fe1—C9−115.99 (8)
C10—C6—Fe1—C3−116.25 (8)C4—C5—Fe1—C1119.38 (11)
C7—C6—Fe1—C4166.36 (8)C8—C9—Fe1—C10119.45 (11)
C10—C6—Fe1—C4−74.85 (9)C8—C9—Fe1—C681.59 (8)
C7—C6—Fe1—C282.31 (9)C10—C9—Fe1—C6−37.87 (7)
C10—C6—Fe1—C2−158.90 (7)C8—C9—Fe1—C3167.31 (12)
C7—C6—Fe1—C8−37.32 (7)C10—C9—Fe1—C347.85 (16)
C10—C6—Fe1—C881.47 (8)C8—C9—Fe1—C4−158.77 (8)
C10—C6—Fe1—C7118.80 (10)C10—C9—Fe1—C481.77 (9)
C7—C6—Fe1—C5−162.29 (16)C8—C9—Fe1—C2−42.8 (2)
C10—C6—Fe1—C5−43.5 (2)C10—C9—Fe1—C2−162.21 (16)
C7—C6—Fe1—C9−81.03 (8)C10—C9—Fe1—C8−119.45 (11)
C10—C6—Fe1—C937.77 (7)C8—C9—Fe1—C737.61 (8)
C7—C6—Fe1—C149.47 (15)C10—C9—Fe1—C7−81.84 (8)
C10—C6—Fe1—C1168.26 (11)C8—C9—Fe1—C5−116.25 (8)
C2—C3—Fe1—C10−159.15 (7)C10—C9—Fe1—C5124.30 (8)
C4—C3—Fe1—C1081.69 (9)C8—C9—Fe1—C1−75.24 (9)
C2—C3—Fe1—C6−116.24 (8)C10—C9—Fe1—C1165.30 (7)
C4—C3—Fe1—C6124.60 (8)C2—C1—Fe1—C10−160.41 (16)
C2—C3—Fe1—C4119.16 (11)C5—C1—Fe1—C10−40.6 (2)
C4—C3—Fe1—C2−119.16 (11)C2—C1—Fe1—C646.28 (16)
C2—C3—Fe1—C8−42.3 (2)C5—C1—Fe1—C6166.14 (11)
C4—C3—Fe1—C8−161.45 (16)C2—C1—Fe1—C3−38.02 (8)
C2—C3—Fe1—C7−75.00 (9)C5—C1—Fe1—C381.84 (9)
C4—C3—Fe1—C7165.84 (8)C2—C1—Fe1—C4−82.22 (9)
C2—C3—Fe1—C581.42 (8)C5—C1—Fe1—C437.64 (8)
C4—C3—Fe1—C5−37.74 (8)C5—C1—Fe1—C2119.86 (11)
C2—C3—Fe1—C9166.68 (11)C2—C1—Fe1—C8124.19 (8)
C4—C3—Fe1—C947.53 (16)C5—C1—Fe1—C8−115.95 (8)
C2—C3—Fe1—C137.73 (8)C2—C1—Fe1—C781.50 (9)
C4—C3—Fe1—C1−81.43 (8)C5—C1—Fe1—C7−158.64 (8)
C5—C4—Fe1—C10124.73 (8)C2—C1—Fe1—C5−119.86 (11)
C3—C4—Fe1—C10−116.26 (8)C2—C1—Fe1—C9165.61 (8)
C5—C4—Fe1—C6166.34 (7)C5—C1—Fe1—C9−74.54 (10)
C3—C4—Fe1—C6−74.65 (9)
D—H···AD—HH···AD···AD—H···A
C14—H14···F1i0.952.543.3249 (15)140
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C14—H14⋯F1i0.952.543.3249 (15)140

Symmetry code: (i) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  1-(4-Bromo-phen-yl)ferrocene.

Authors:  Vincent O Nyamori; Muhammad D Bala
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-09

3.  1-(6-Ferrocenylhex-yl)-1H-imidazole.

Authors:  Vincent O Nyamori; Muhammad D Bala; Demetrius C Levendis
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-17
  3 in total
  2 in total

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

Authors:  Vincent O Nyamori; Siphesihle M Zulu; Bernard Omondi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-10

2.  (4-{[(Pyridin-4-yl)methyl-idene]amino}-phen-yl)ferrocene.

Authors:  Vincent O Nyamori; Godfrey Keru; Bernard Omondi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-24
  2 in total

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