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metal-organic compounds
1,4-Diferrocenyl-2-methylpiperazine-1,4-diium bis(trifluoroacetate)
aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: fangc2009@yahoo.cn
In the title compound, [Fe2(C5H5)2(C17H24N2)](CF3COO)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 cyclopentadiene rings vary from 2.025 (6) to 2.044 (6) Å. Intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the cations and anions into a three-dimensional network.
Related literature
For the applications of ferrocene derivatives, see: Yang et al. (2002); Togni & Hayashi (1995
); Long (1995
); Roberto et al. (2000
). For the of related compounds, see: Hess et al. (1999
); Base et al. (2002
); For the synthetic strategy, see: Chen (2009
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrystalClear (Rigaku, 2005); cell 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.
Supporting information
10.1107/S160053680902426X/rz2338sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680902426X/rz2338Isup2.hkl
The preparation of S-1,4-ferrocenyl-2-methylpiperazine is analogous to that of 2,2'-diferrocenyl-5,5'-(m-phenylene)di-2H-tetrazole (Chen, 2009). To a mixture of [Fe(C5H5)(C5H4)N+(CH3)3I-] (10 mmol) in H2O (50 ml) was added S-2-methylpiperazine (5 mmol) and the mixture was heated to reflux temperature for 5 h. Then, the formed precipitate was filtered, the obtained yellow solid was purified enough without further disposal (yield: 78%). For the preparation of the title compound, a solution of trifluoroacetic acid (4 mmol) in ethanol was added to a solution of S-1,4-ferrocenyl-2-methylpiperazine (2 mmol) in dichloromethane/ethanol (1:1 v/v) and the mixture stirred for 1 h at room temperature. Red crystals suitable for X-ray
were obtained by slow evaporation of the solution at room temperature after 5 days.Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on the parent atoms, with C—H = 0.96-0.98 Å, N—H = 0.91 Å and with Uiso(H) = 1.2Uiso(C, N) or 1.2Uiso(C) for methyl H atoms. The methyl group is disordered over two positions related by a centre of symmetry, with site occupancy factors of 0.5.
Data collection: CrystalClear (Rigaku, 2005); cell
CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).[Fe2(C5H5)2(C17H24N2)](C2F3O2)2 | F(000) = 744.0 |
Mr = 724.30 | Dx = 1.534 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3933 reflections |
a = 11.922 (3) Å | θ = 2.6–27.5° |
b = 9.7977 (16) Å | µ = 1.00 mm−1 |
c = 13.628 (4) Å | T = 293 K |
β = 99.998 (15)° | Block, red |
V = 1567.7 (7) Å3 | 0.27 × 0.25 × 0.20 mm |
Z = 2 |
Rigaku SCXmini diffractometer | 3592 independent reflections |
Radiation source: fine-focus sealed tube | 3117 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5°, θmin = 2.5° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −12→12 |
Tmin = 0.771, Tmax = 0.819 | l = −17→17 |
15611 measured reflections |
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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.224 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1088P)2 + 3.5578P] where P = (Fo2 + 2Fc2)/3 |
3592 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 1.06 e Å−3 |
0 restraints | Δρmin = −0.71 e Å−3 |
[Fe2(C5H5)2(C17H24N2)](C2F3O2)2 | V = 1567.7 (7) Å3 |
Mr = 724.30 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.922 (3) Å | µ = 1.00 mm−1 |
b = 9.7977 (16) Å | T = 293 K |
c = 13.628 (4) Å | 0.27 × 0.25 × 0.20 mm |
β = 99.998 (15)° |
Rigaku SCXmini diffractometer | 3592 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 3117 reflections with I > 2σ(I) |
Tmin = 0.771, Tmax = 0.819 | Rint = 0.042 |
15611 measured reflections |
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.224 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.06 e Å−3 |
3592 reflections | Δρmin = −0.71 e Å−3 |
209 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.07028 (5) | 0.09197 (7) | 0.20528 (5) | 0.0426 (3) | |
N1 | 0.0206 (3) | 0.3711 (4) | 0.4525 (3) | 0.0398 (8) | |
H1A | −0.0408 | 0.3234 | 0.4651 | 0.048* | |
C1 | 0.0197 (4) | 0.2288 (5) | 0.3010 (3) | 0.0451 (10) | |
C13 | 0.0910 (4) | 0.4133 (5) | 0.5509 (4) | 0.0488 (11) | |
H13A | 0.1587 | 0.4611 | 0.5394 | 0.059* | |
H13B | 0.1147 | 0.3329 | 0.5907 | 0.059* | 0.50 |
C7 | 0.2223 (5) | 0.0916 (6) | 0.1564 (5) | 0.0591 (13) | |
H7 | 0.2594 | 0.1718 | 0.1333 | 0.071* | |
C12 | −0.0211 (4) | 0.4941 (5) | 0.3933 (3) | 0.0449 (10) | |
H12A | −0.0675 | 0.4657 | 0.3310 | 0.054* | |
H12B | 0.0435 | 0.5447 | 0.3777 | 0.054* | |
C11 | 0.0902 (4) | 0.2780 (5) | 0.3958 (3) | 0.0469 (10) | |
H11A | 0.1556 | 0.3276 | 0.3809 | 0.056* | |
H11B | 0.1178 | 0.2004 | 0.4372 | 0.056* | |
C8 | 0.1457 (5) | 0.0064 (6) | 0.0967 (4) | 0.0614 (14) | |
H8 | 0.1201 | 0.0160 | 0.0247 | 0.074* | |
C5 | −0.0521 (5) | 0.1107 (6) | 0.2920 (4) | 0.0583 (14) | |
H5 | −0.0641 | 0.0495 | 0.3462 | 0.070* | |
C2 | 0.0127 (5) | 0.2876 (6) | 0.2044 (4) | 0.0569 (13) | |
H2 | 0.0527 | 0.3694 | 0.1876 | 0.068* | |
C6 | 0.2371 (5) | 0.0449 (7) | 0.2551 (5) | 0.0642 (15) | |
H6 | 0.2864 | 0.0864 | 0.3123 | 0.077* | |
C9 | 0.1104 (6) | −0.0962 (6) | 0.1582 (6) | 0.0747 (19) | |
H9 | 0.0572 | −0.1710 | 0.1367 | 0.090* | |
C3 | −0.0642 (5) | 0.2062 (7) | 0.1373 (5) | 0.0707 (18) | |
H3 | −0.0851 | 0.2215 | 0.0654 | 0.085* | |
C4 | −0.1032 (5) | 0.0992 (7) | 0.1902 (6) | 0.075 (2) | |
H4 | −0.1560 | 0.0272 | 0.1616 | 0.090* | |
C10 | 0.1680 (6) | −0.0701 (7) | 0.2578 (5) | 0.0748 (19) | |
H10 | 0.1612 | −0.1240 | 0.3170 | 0.090* | |
O1 | 0.8567 (4) | 0.2055 (6) | 0.4984 (3) | 0.0771 (13) | |
O2 | 0.7403 (5) | 0.3147 (6) | 0.3831 (5) | 0.1058 (19) | |
C15 | 0.6838 (6) | 0.1017 (7) | 0.4333 (6) | 0.0715 (17) | |
C14 | 0.7705 (5) | 0.2200 (7) | 0.4397 (5) | 0.0664 (15) | |
F2 | 0.6434 (12) | 0.0677 (12) | 0.3507 (5) | 0.283 (8) | |
F3 | 0.6053 (8) | 0.1223 (11) | 0.4759 (11) | 0.257 (6) | |
F1 | 0.7170 (8) | −0.0077 (8) | 0.4721 (10) | 0.240 (6) | |
C16 | 0.1208 (9) | 0.2777 (11) | 0.6216 (8) | 0.056 (2) | 0.50 |
H16A | 0.0515 | 0.2310 | 0.6276 | 0.084* | 0.50 |
H16B | 0.1590 | 0.3051 | 0.6865 | 0.084* | 0.50 |
H16C | 0.1692 | 0.2177 | 0.5920 | 0.084* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0450 (4) | 0.0407 (4) | 0.0431 (4) | 0.0050 (3) | 0.0104 (3) | −0.0119 (3) |
N1 | 0.0385 (18) | 0.0455 (19) | 0.0358 (17) | −0.0006 (15) | 0.0072 (14) | −0.0136 (15) |
C1 | 0.047 (2) | 0.044 (2) | 0.046 (2) | 0.0033 (19) | 0.0123 (19) | −0.0150 (19) |
C13 | 0.045 (2) | 0.057 (3) | 0.042 (2) | 0.005 (2) | −0.0001 (18) | −0.015 (2) |
C7 | 0.055 (3) | 0.060 (3) | 0.068 (3) | 0.001 (2) | 0.027 (3) | −0.010 (3) |
C12 | 0.050 (2) | 0.048 (2) | 0.037 (2) | 0.003 (2) | 0.0074 (18) | −0.0122 (19) |
C11 | 0.047 (2) | 0.053 (3) | 0.042 (2) | 0.005 (2) | 0.0113 (18) | −0.014 (2) |
C8 | 0.067 (3) | 0.070 (3) | 0.051 (3) | 0.009 (3) | 0.019 (2) | −0.020 (3) |
C5 | 0.055 (3) | 0.057 (3) | 0.069 (3) | −0.007 (2) | 0.025 (3) | −0.027 (3) |
C2 | 0.073 (3) | 0.048 (3) | 0.049 (3) | 0.020 (2) | 0.010 (2) | −0.010 (2) |
C6 | 0.052 (3) | 0.072 (4) | 0.067 (3) | 0.016 (3) | 0.006 (2) | −0.013 (3) |
C9 | 0.075 (4) | 0.042 (3) | 0.113 (6) | 0.002 (3) | 0.031 (4) | −0.024 (3) |
C3 | 0.072 (4) | 0.078 (4) | 0.054 (3) | 0.030 (3) | −0.010 (3) | −0.024 (3) |
C4 | 0.041 (3) | 0.086 (4) | 0.096 (5) | −0.003 (3) | 0.006 (3) | −0.056 (4) |
C10 | 0.090 (5) | 0.061 (4) | 0.079 (4) | 0.035 (3) | 0.030 (4) | 0.021 (3) |
O1 | 0.063 (2) | 0.113 (4) | 0.057 (2) | −0.015 (2) | 0.017 (2) | −0.009 (2) |
O2 | 0.104 (4) | 0.068 (3) | 0.138 (5) | 0.003 (3) | 0.001 (4) | 0.025 (3) |
C15 | 0.063 (4) | 0.069 (4) | 0.082 (4) | −0.015 (3) | 0.013 (3) | −0.001 (3) |
C14 | 0.063 (3) | 0.076 (4) | 0.062 (3) | 0.004 (3) | 0.018 (3) | −0.021 (3) |
F2 | 0.427 (15) | 0.321 (12) | 0.086 (4) | −0.306 (13) | 0.004 (7) | −0.023 (6) |
F3 | 0.156 (7) | 0.224 (10) | 0.436 (18) | −0.078 (7) | 0.181 (10) | −0.056 (11) |
F1 | 0.200 (8) | 0.099 (5) | 0.378 (15) | −0.057 (5) | −0.075 (9) | 0.070 (7) |
C16 | 0.061 (6) | 0.050 (5) | 0.053 (5) | 0.008 (5) | 0.002 (4) | −0.012 (4) |
Fe1—C10 | 2.025 (6) | C12—H12B | 0.9700 |
Fe1—C1 | 2.034 (4) | C11—H11A | 0.9700 |
Fe1—C2 | 2.035 (5) | C11—H11B | 0.9700 |
Fe1—C7 | 2.036 (5) | C8—C9 | 1.419 (9) |
Fe1—C9 | 2.036 (5) | C8—H8 | 0.9800 |
Fe1—C6 | 2.039 (6) | C5—C4 | 1.420 (9) |
Fe1—C5 | 2.040 (5) | C5—H5 | 0.9800 |
Fe1—C8 | 2.041 (5) | C2—C3 | 1.422 (8) |
Fe1—C3 | 2.041 (6) | C2—H2 | 0.9800 |
Fe1—C4 | 2.044 (6) | C6—C10 | 1.400 (10) |
N1—C12 | 1.487 (6) | C6—H6 | 0.9800 |
N1—C13 | 1.511 (5) | C9—C10 | 1.433 (10) |
N1—C11 | 1.529 (5) | C9—H9 | 0.9800 |
N1—H1A | 0.9100 | C3—C4 | 1.397 (10) |
C1—C2 | 1.426 (7) | C3—H3 | 0.9800 |
C1—C5 | 1.432 (7) | C4—H4 | 0.9800 |
C1—C11 | 1.493 (6) | C10—H10 | 0.9800 |
C13—C12i | 1.521 (6) | O1—C14 | 1.197 (8) |
C13—C16 | 1.643 (12) | O2—C14 | 1.220 (8) |
C13—H13A | 0.9700 | C15—F2 | 1.192 (9) |
C13—H13B | 0.9700 | C15—F3 | 1.201 (11) |
C7—C8 | 1.391 (8) | C15—F1 | 1.229 (10) |
C7—C6 | 1.402 (9) | C15—C14 | 1.546 (9) |
C7—H7 | 0.9800 | C16—H16A | 0.9600 |
C12—C13i | 1.521 (6) | C16—H16B | 0.9600 |
C12—H12A | 0.9700 | C16—H16C | 0.9600 |
C10—Fe1—C1 | 120.4 (3) | C13i—C12—H12A | 109.2 |
C10—Fe1—C2 | 155.9 (3) | N1—C12—H12B | 109.2 |
C1—Fe1—C2 | 41.0 (2) | C13i—C12—H12B | 109.2 |
C10—Fe1—C7 | 67.9 (3) | H12A—C12—H12B | 107.9 |
C1—Fe1—C7 | 126.2 (2) | C1—C11—N1 | 110.9 (4) |
C2—Fe1—C7 | 108.6 (2) | C1—C11—H11A | 109.5 |
C10—Fe1—C9 | 41.3 (3) | N1—C11—H11A | 109.5 |
C1—Fe1—C9 | 155.6 (3) | C1—C11—H11B | 109.5 |
C2—Fe1—C9 | 161.5 (3) | N1—C11—H11B | 109.5 |
C7—Fe1—C9 | 67.9 (3) | H11A—C11—H11B | 108.0 |
C10—Fe1—C6 | 40.3 (3) | C7—C8—C9 | 108.1 (5) |
C1—Fe1—C6 | 108.4 (2) | C7—C8—Fe1 | 69.9 (3) |
C2—Fe1—C6 | 121.5 (3) | C9—C8—Fe1 | 69.5 (3) |
C7—Fe1—C6 | 40.2 (2) | C7—C8—H8 | 125.9 |
C9—Fe1—C6 | 68.4 (3) | C9—C8—H8 | 125.9 |
C10—Fe1—C5 | 106.9 (3) | Fe1—C8—H8 | 125.9 |
C1—Fe1—C5 | 41.2 (2) | C4—C5—C1 | 107.2 (6) |
C2—Fe1—C5 | 69.1 (2) | C4—C5—Fe1 | 69.8 (3) |
C7—Fe1—C5 | 163.1 (2) | C1—C5—Fe1 | 69.2 (3) |
C9—Fe1—C5 | 119.7 (3) | C4—C5—H5 | 126.4 |
C6—Fe1—C5 | 125.6 (3) | C1—C5—H5 | 126.4 |
C10—Fe1—C8 | 68.6 (3) | Fe1—C5—H5 | 126.4 |
C1—Fe1—C8 | 162.4 (2) | C3—C2—C1 | 107.2 (6) |
C2—Fe1—C8 | 125.0 (2) | C3—C2—Fe1 | 69.8 (3) |
C7—Fe1—C8 | 39.9 (2) | C1—C2—Fe1 | 69.4 (3) |
C9—Fe1—C8 | 40.8 (3) | C3—C2—H2 | 126.4 |
C6—Fe1—C8 | 67.8 (2) | C1—C2—H2 | 126.4 |
C5—Fe1—C8 | 155.1 (2) | Fe1—C2—H2 | 126.4 |
C10—Fe1—C3 | 161.6 (3) | C10—C6—C7 | 108.1 (6) |
C1—Fe1—C3 | 68.5 (2) | C10—C6—Fe1 | 69.3 (3) |
C2—Fe1—C3 | 40.8 (2) | C7—C6—Fe1 | 69.8 (3) |
C7—Fe1—C3 | 121.7 (3) | C10—C6—H6 | 125.9 |
C9—Fe1—C3 | 124.2 (3) | C7—C6—H6 | 125.9 |
C6—Fe1—C3 | 156.7 (3) | Fe1—C6—H6 | 125.9 |
C5—Fe1—C3 | 68.2 (3) | C8—C9—C10 | 106.9 (6) |
C8—Fe1—C3 | 107.8 (2) | C8—C9—Fe1 | 69.8 (3) |
C10—Fe1—C4 | 124.9 (3) | C10—C9—Fe1 | 68.9 (3) |
C1—Fe1—C4 | 68.5 (2) | C8—C9—H9 | 126.5 |
C2—Fe1—C4 | 68.4 (3) | C10—C9—H9 | 126.5 |
C7—Fe1—C4 | 155.5 (3) | Fe1—C9—H9 | 126.5 |
C9—Fe1—C4 | 106.8 (3) | C4—C3—C2 | 108.9 (5) |
C6—Fe1—C4 | 162.3 (3) | C4—C3—Fe1 | 70.1 (3) |
C5—Fe1—C4 | 40.7 (3) | C2—C3—Fe1 | 69.4 (3) |
C8—Fe1—C4 | 120.5 (2) | C4—C3—H3 | 125.6 |
C3—Fe1—C4 | 40.0 (3) | C2—C3—H3 | 125.6 |
C12—N1—C13 | 110.0 (3) | Fe1—C3—H3 | 125.6 |
C12—N1—C11 | 111.6 (3) | C3—C4—C5 | 108.7 (5) |
C13—N1—C11 | 110.2 (3) | C3—C4—Fe1 | 69.9 (3) |
C12—N1—H1A | 108.3 | C5—C4—Fe1 | 69.5 (3) |
C13—N1—H1A | 108.3 | C3—C4—H4 | 125.7 |
C11—N1—H1A | 108.3 | C5—C4—H4 | 125.7 |
C2—C1—C5 | 108.0 (5) | Fe1—C4—H4 | 125.7 |
C2—C1—C11 | 127.0 (5) | C6—C10—C9 | 107.8 (6) |
C5—C1—C11 | 125.0 (5) | C6—C10—Fe1 | 70.4 (3) |
C2—C1—Fe1 | 69.5 (3) | C9—C10—Fe1 | 69.8 (3) |
C5—C1—Fe1 | 69.7 (3) | C6—C10—H10 | 126.1 |
C11—C1—Fe1 | 125.7 (3) | C9—C10—H10 | 126.1 |
N1—C13—C12i | 109.8 (4) | Fe1—C10—H10 | 126.1 |
N1—C13—C16 | 109.2 (5) | F2—C15—F3 | 106.4 (11) |
C12i—C13—C16 | 105.7 (5) | F2—C15—F1 | 102.1 (10) |
N1—C13—H13A | 109.7 | F3—C15—F1 | 99.1 (10) |
C12i—C13—H13A | 109.7 | F2—C15—C14 | 114.8 (7) |
C16—C13—H13A | 112.6 | F3—C15—C14 | 114.6 (7) |
N1—C13—H13B | 109.7 | F1—C15—C14 | 117.8 (7) |
C12i—C13—H13B | 109.7 | O1—C14—O2 | 129.7 (7) |
H13A—C13—H13B | 108.2 | O1—C14—C15 | 115.9 (7) |
C8—C7—C6 | 109.0 (5) | O2—C14—C15 | 114.4 (6) |
C8—C7—Fe1 | 70.2 (3) | C13—C16—H16A | 109.5 |
C6—C7—Fe1 | 70.0 (3) | C13—C16—H16B | 109.5 |
C8—C7—H7 | 125.5 | H16A—C16—H16B | 109.5 |
C6—C7—H7 | 125.5 | C13—C16—H16C | 109.5 |
Fe1—C7—H7 | 125.5 | H16A—C16—H16C | 109.5 |
N1—C12—C13i | 111.9 (4) | H16B—C16—H16C | 109.5 |
N1—C12—H12A | 109.2 |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1ii | 0.91 | 1.80 | 2.696 (6) | 169 |
C4—H4···O2iii | 0.98 | 2.35 | 3.306 (9) | 163 |
Symmetry codes: (ii) x−1, y, z; (iii) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe2(C5H5)2(C17H24N2)](C2F3O2)2 |
Mr | 724.30 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.922 (3), 9.7977 (16), 13.628 (4) |
β (°) | 99.998 (15) |
V (Å3) | 1567.7 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.00 |
Crystal size (mm) | 0.27 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Rigaku SCXmini diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.771, 0.819 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15611, 3592, 3117 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.078, 0.224, 1.07 |
No. of reflections | 3592 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.06, −0.71 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.91 | 1.80 | 2.696 (6) | 169.4 |
C4—H4···O2ii | 0.98 | 2.35 | 3.306 (9) | 163.4 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
This work was supported by a start-up grant from Southeast University.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The chemistry of ferrocene has received much attention because of its applications in many fields, such as in catalysis (Yang et al., 2002), non-linear optical (NLO) materials (Long, 1995; Roberto et al., 2000), organic or organometallic synthesis and materials (Togni & Hayashi, 1995), and so on. As part of our on-going studies on new ferrocene compounds, the crystal structure of the title compound is reported herein.
The title compound (Fig. 1) consists of centrosymmetric 1,4-ferrocenyl-2-methylpiperazinium cations and trifluoroacetate anions in the stroichiometric ratio of 1:2. The methyl group of the cation is disordered over two positions of equal occupancy related by the symmetry operator (-x, 1-y, 1-z). The deformation of the 1,4-ferrocenyl-2-methylpiperazinium cation is reflected in the values of the C12A—C13—N1, C13—N1—C12, N1—C12—C13A angles, which are 109.8 (4), 110.0 (3), 111.9 (4)°, respectively [symmetry code: (A) -x, 1-y, 1-z]. The Fe—C distances to the two cyclopentadiene rings are normal, ranging from 2.025 (6) to 2.044 (6) Å (Hess et al., 1999; Base et al., 2002). The two cyclopentadiene rings are nearly parallel, forming a dihedral angle of 1.1 (2)°. In the crystal packing (Fig. 2), intermolecular N—H···O and C—H···O interactions (Table 1) link cations and anions into a hydrogen-bonded network, which stabilizes the crystal packing (Fig.2).