Literature DB >> 21583407

1,4-Diferrocenyl-2-methyl-piperazine-1,4-diium bis-(trifluoro-acetate).

Fang Chen1.   

Abstract

In the title compound, [Fe(2)(C(5)H(5))(2)(C(17)H(24)N(2))](CF(3)COO)(2), the cation possesses a crystallographically imposed inversion centre. The methyl group is disordered over two positions of equal occupancy. The Fe-C bond lengths to the two cyclo-penta-diene rings vary from 2.025 (6) to 2.044 (6) Å. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the cations and anions into a three-dimensional network.

Entities:  

Year:  2009        PMID： 21583407      PMCID： PMC2977395          DOI： 10.1107/S160053680902426X

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


Related literature

For the applications of ferrocene derivatives, see: Yang et al. (2002 ▶); Togni & Hayashi (1995 ▶); Long (1995 ▶); Roberto et al. (2000 ▶). For the crystal structure of related compounds, see: Hess et al. (1999 ▶); Base et al. (2002 ▶); For the synthetic strategy, see: Chen (2009 ▶).

Experimental

Crystal data

[Fe2(C5H5)2(C17H24N2)](C2F3O2)2 M = 724.30 Monoclinic, a = 11.922 (3) Å b = 9.7977 (16) Å c = 13.628 (4) Å β = 99.998 (15)° V = 1567.7 (7) Å3 Z = 2 Mo Kα radiation μ = 1.00 mm−1 T = 293 K 0.27 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.771, T max = 0.819 15611 measured reflections 3592 independent reflections 3117 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.078 wR(F 2) = 0.224 S = 1.07 3592 reflections 209 parameters H-atom parameters constrained Δρmax = 1.06 e Å−3 Δρmin = −0.71 e Å−3 Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902426X/rz2338sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680902426X/rz2338Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Fe2(C5H5)2(C17H24N2)](C2F3O2)2F(000) = 744.0
Mr = 724.30Dx = 1.534 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3933 reflections
a = 11.922 (3) Åθ = 2.6–27.5°
b = 9.7977 (16) ŵ = 1.00 mm−1
c = 13.628 (4) ÅT = 293 K
β = 99.998 (15)°Block, red
V = 1567.7 (7) Å30.27 × 0.25 × 0.20 mm
Z = 2
Rigaku SCXmini diffractometer3592 independent reflections
Radiation source: fine-focus sealed tube3117 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.5°
ω scansh = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −12→12
Tmin = 0.771, Tmax = 0.819l = −17→17
15611 measured 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)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.224H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1088P)2 + 3.5578P] where P = (Fo2 + 2Fc2)/3
3592 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 1.06 e Å−3
0 restraintsΔρmin = −0.70 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.
xyzUiso*/UeqOcc. (<1)
Fe10.07028 (5)0.09197 (7)0.20528 (5)0.0426 (3)
N10.0206 (3)0.3711 (4)0.4525 (3)0.0398 (8)
H1A−0.04080.32340.46510.048*
C10.0197 (4)0.2288 (5)0.3010 (3)0.0451 (10)
C130.0910 (4)0.4133 (5)0.5509 (4)0.0488 (11)
H13A0.15870.46110.53940.059*
H13B0.11470.33290.59070.059*0.50
C70.2223 (5)0.0916 (6)0.1564 (5)0.0591 (13)
H70.25940.17180.13330.071*
C12−0.0211 (4)0.4941 (5)0.3933 (3)0.0449 (10)
H12A−0.06750.46570.33100.054*
H12B0.04350.54470.37770.054*
C110.0902 (4)0.2780 (5)0.3958 (3)0.0469 (10)
H11A0.15560.32760.38090.056*
H11B0.11780.20040.43720.056*
C80.1457 (5)0.0064 (6)0.0967 (4)0.0614 (14)
H80.12010.01600.02470.074*
C5−0.0521 (5)0.1107 (6)0.2920 (4)0.0583 (14)
H5−0.06410.04950.34620.070*
C20.0127 (5)0.2876 (6)0.2044 (4)0.0569 (13)
H20.05270.36940.18760.068*
C60.2371 (5)0.0449 (7)0.2551 (5)0.0642 (15)
H60.28640.08640.31230.077*
C90.1104 (6)−0.0962 (6)0.1582 (6)0.0747 (19)
H90.0572−0.17100.13670.090*
C3−0.0642 (5)0.2062 (7)0.1373 (5)0.0707 (18)
H3−0.08510.22150.06540.085*
C4−0.1032 (5)0.0992 (7)0.1902 (6)0.075 (2)
H4−0.15600.02720.16160.090*
C100.1680 (6)−0.0701 (7)0.2578 (5)0.0748 (19)
H100.1612−0.12400.31700.090*
O10.8567 (4)0.2055 (6)0.4984 (3)0.0771 (13)
O20.7403 (5)0.3147 (6)0.3831 (5)0.1058 (19)
C150.6838 (6)0.1017 (7)0.4333 (6)0.0715 (17)
C140.7705 (5)0.2200 (7)0.4397 (5)0.0664 (15)
F20.6434 (12)0.0677 (12)0.3507 (5)0.283 (8)
F30.6053 (8)0.1223 (11)0.4759 (11)0.257 (6)
F10.7170 (8)−0.0077 (8)0.4721 (10)0.240 (6)
C160.1208 (9)0.2777 (11)0.6216 (8)0.056 (2)0.50
H16A0.05150.23100.62760.084*0.50
H16B0.15900.30510.68650.084*0.50
H16C0.16920.21770.59200.084*0.50
U11U22U33U12U13U23
Fe10.0450 (4)0.0407 (4)0.0431 (4)0.0050 (3)0.0104 (3)−0.0119 (3)
N10.0385 (18)0.0455 (19)0.0358 (17)−0.0006 (15)0.0072 (14)−0.0136 (15)
C10.047 (2)0.044 (2)0.046 (2)0.0033 (19)0.0123 (19)−0.0150 (19)
C130.045 (2)0.057 (3)0.042 (2)0.005 (2)−0.0001 (18)−0.015 (2)
C70.055 (3)0.060 (3)0.068 (3)0.001 (2)0.027 (3)−0.010 (3)
C120.050 (2)0.048 (2)0.037 (2)0.003 (2)0.0074 (18)−0.0122 (19)
C110.047 (2)0.053 (3)0.042 (2)0.005 (2)0.0113 (18)−0.014 (2)
C80.067 (3)0.070 (3)0.051 (3)0.009 (3)0.019 (2)−0.020 (3)
C50.055 (3)0.057 (3)0.069 (3)−0.007 (2)0.025 (3)−0.027 (3)
C20.073 (3)0.048 (3)0.049 (3)0.020 (2)0.010 (2)−0.010 (2)
C60.052 (3)0.072 (4)0.067 (3)0.016 (3)0.006 (2)−0.013 (3)
C90.075 (4)0.042 (3)0.113 (6)0.002 (3)0.031 (4)−0.024 (3)
C30.072 (4)0.078 (4)0.054 (3)0.030 (3)−0.010 (3)−0.024 (3)
C40.041 (3)0.086 (4)0.096 (5)−0.003 (3)0.006 (3)−0.056 (4)
C100.090 (5)0.061 (4)0.079 (4)0.035 (3)0.030 (4)0.021 (3)
O10.063 (2)0.113 (4)0.057 (2)−0.015 (2)0.017 (2)−0.009 (2)
O20.104 (4)0.068 (3)0.138 (5)0.003 (3)0.001 (4)0.025 (3)
C150.063 (4)0.069 (4)0.082 (4)−0.015 (3)0.013 (3)−0.001 (3)
C140.063 (3)0.076 (4)0.062 (3)0.004 (3)0.018 (3)−0.021 (3)
F20.427 (15)0.321 (12)0.086 (4)−0.306 (13)0.004 (7)−0.023 (6)
F30.156 (7)0.224 (10)0.436 (18)−0.078 (7)0.181 (10)−0.056 (11)
F10.200 (8)0.099 (5)0.378 (15)−0.057 (5)−0.075 (9)0.070 (7)
C160.061 (6)0.050 (5)0.053 (5)0.008 (5)0.002 (4)−0.012 (4)
Fe1—C102.025 (6)C12—H12B0.9700
Fe1—C12.034 (4)C11—H11A0.9700
Fe1—C22.035 (5)C11—H11B0.9700
Fe1—C72.036 (5)C8—C91.419 (9)
Fe1—C92.036 (5)C8—H80.9800
Fe1—C62.039 (6)C5—C41.420 (9)
Fe1—C52.040 (5)C5—H50.9800
Fe1—C82.041 (5)C2—C31.422 (8)
Fe1—C32.041 (6)C2—H20.9800
Fe1—C42.044 (6)C6—C101.400 (10)
N1—C121.487 (6)C6—H60.9800
N1—C131.511 (5)C9—C101.433 (10)
N1—C111.529 (5)C9—H90.9800
N1—H1A0.9100C3—C41.397 (10)
C1—C21.426 (7)C3—H30.9800
C1—C51.432 (7)C4—H40.9800
C1—C111.493 (6)C10—H100.9800
C13—C12i1.521 (6)O1—C141.197 (8)
C13—C161.643 (12)O2—C141.220 (8)
C13—H13A0.9700C15—F21.192 (9)
C13—H13B0.9700C15—F31.201 (11)
C7—C81.391 (8)C15—F11.229 (10)
C7—C61.402 (9)C15—C141.546 (9)
C7—H70.9800C16—H16A0.9600
C12—C13i1.521 (6)C16—H16B0.9600
C12—H12A0.9700C16—H16C0.9600
C10—Fe1—C1120.4 (3)C13i—C12—H12A109.2
C10—Fe1—C2155.9 (3)N1—C12—H12B109.2
C1—Fe1—C241.0 (2)C13i—C12—H12B109.2
C10—Fe1—C767.9 (3)H12A—C12—H12B107.9
C1—Fe1—C7126.2 (2)C1—C11—N1110.9 (4)
C2—Fe1—C7108.6 (2)C1—C11—H11A109.5
C10—Fe1—C941.3 (3)N1—C11—H11A109.5
C1—Fe1—C9155.6 (3)C1—C11—H11B109.5
C2—Fe1—C9161.5 (3)N1—C11—H11B109.5
C7—Fe1—C967.9 (3)H11A—C11—H11B108.0
C10—Fe1—C640.3 (3)C7—C8—C9108.1 (5)
C1—Fe1—C6108.4 (2)C7—C8—Fe169.9 (3)
C2—Fe1—C6121.5 (3)C9—C8—Fe169.5 (3)
C7—Fe1—C640.2 (2)C7—C8—H8125.9
C9—Fe1—C668.4 (3)C9—C8—H8125.9
C10—Fe1—C5106.9 (3)Fe1—C8—H8125.9
C1—Fe1—C541.2 (2)C4—C5—C1107.2 (6)
C2—Fe1—C569.1 (2)C4—C5—Fe169.8 (3)
C7—Fe1—C5163.1 (2)C1—C5—Fe169.2 (3)
C9—Fe1—C5119.7 (3)C4—C5—H5126.4
C6—Fe1—C5125.6 (3)C1—C5—H5126.4
C10—Fe1—C868.6 (3)Fe1—C5—H5126.4
C1—Fe1—C8162.4 (2)C3—C2—C1107.2 (6)
C2—Fe1—C8125.0 (2)C3—C2—Fe169.8 (3)
C7—Fe1—C839.9 (2)C1—C2—Fe169.4 (3)
C9—Fe1—C840.8 (3)C3—C2—H2126.4
C6—Fe1—C867.8 (2)C1—C2—H2126.4
C5—Fe1—C8155.1 (2)Fe1—C2—H2126.4
C10—Fe1—C3161.6 (3)C10—C6—C7108.1 (6)
C1—Fe1—C368.5 (2)C10—C6—Fe169.3 (3)
C2—Fe1—C340.8 (2)C7—C6—Fe169.8 (3)
C7—Fe1—C3121.7 (3)C10—C6—H6125.9
C9—Fe1—C3124.2 (3)C7—C6—H6125.9
C6—Fe1—C3156.7 (3)Fe1—C6—H6125.9
C5—Fe1—C368.2 (3)C8—C9—C10106.9 (6)
C8—Fe1—C3107.8 (2)C8—C9—Fe169.8 (3)
C10—Fe1—C4124.9 (3)C10—C9—Fe168.9 (3)
C1—Fe1—C468.5 (2)C8—C9—H9126.5
C2—Fe1—C468.4 (3)C10—C9—H9126.5
C7—Fe1—C4155.5 (3)Fe1—C9—H9126.5
C9—Fe1—C4106.8 (3)C4—C3—C2108.9 (5)
C6—Fe1—C4162.3 (3)C4—C3—Fe170.1 (3)
C5—Fe1—C440.7 (3)C2—C3—Fe169.4 (3)
C8—Fe1—C4120.5 (2)C4—C3—H3125.6
C3—Fe1—C440.0 (3)C2—C3—H3125.6
C12—N1—C13110.0 (3)Fe1—C3—H3125.6
C12—N1—C11111.6 (3)C3—C4—C5108.7 (5)
C13—N1—C11110.2 (3)C3—C4—Fe169.9 (3)
C12—N1—H1A108.3C5—C4—Fe169.5 (3)
C13—N1—H1A108.3C3—C4—H4125.7
C11—N1—H1A108.3C5—C4—H4125.7
C2—C1—C5108.0 (5)Fe1—C4—H4125.7
C2—C1—C11127.0 (5)C6—C10—C9107.8 (6)
C5—C1—C11125.0 (5)C6—C10—Fe170.4 (3)
C2—C1—Fe169.5 (3)C9—C10—Fe169.8 (3)
C5—C1—Fe169.7 (3)C6—C10—H10126.1
C11—C1—Fe1125.7 (3)C9—C10—H10126.1
N1—C13—C12i109.8 (4)Fe1—C10—H10126.1
N1—C13—C16109.2 (5)F2—C15—F3106.4 (11)
C12i—C13—C16105.7 (5)F2—C15—F1102.1 (10)
N1—C13—H13A109.7F3—C15—F199.1 (10)
C12i—C13—H13A109.7F2—C15—C14114.8 (7)
C16—C13—H13A112.6F3—C15—C14114.6 (7)
N1—C13—H13B109.7F1—C15—C14117.8 (7)
C12i—C13—H13B109.7O1—C14—O2129.7 (7)
H13A—C13—H13B108.2O1—C14—C15115.9 (7)
C8—C7—C6109.0 (5)O2—C14—C15114.4 (6)
C8—C7—Fe170.2 (3)C13—C16—H16A109.5
C6—C7—Fe170.0 (3)C13—C16—H16B109.5
C8—C7—H7125.5H16A—C16—H16B109.5
C6—C7—H7125.5C13—C16—H16C109.5
Fe1—C7—H7125.5H16A—C16—H16C109.5
N1—C12—C13i111.9 (4)H16B—C16—H16C109.5
N1—C12—H12A109.2
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1ii0.911.802.696 (6)169
C4—H4···O2iii0.982.353.306 (9)163
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯O1i0.911.802.696 (6)169
C4—H4⋯O2ii0.982.353.306 (9)163

Symmetry codes: (i) ; (ii) .

  3 in total

1.  N-(ferrocenecarbonyl)-N'-(quinolin-8-yl)thiourea.

Authors:  Jia-Xiang Yang; Yu-Peng Tian; Qing-Liang Liu; Yong-Shu Xie; Hoong-Kun Fun; Suchada Chantrapromma; Ibrahim Abdul Razak
Journal:  Acta Crystallogr C       Date:  2001-12-22       Impact factor: 1.172

2.  A short history of SHELX.

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

3.  2,2'-Bis(ferrocenylmethyl)-5,5'-(m-phenyl-ene)di-2H-tetra-zole.

Authors:  Fang Chen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-17
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