1,4-Diferrocenyl-2-methyl­piperazine-1,4-diium bis­(trifluoro­acetate)

Chen, F.

doi:10.1107/S160053680902426X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m961

doi:10.1107/S160053680902426X

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1,4-Diferrocenyl-2-methylpiperazine-1,4-diium bis(trifluoroacetate)

Fang Chen ^a ^*

^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

(Received 18 June 2009; accepted 1 July 2009; online 22 July 2009)

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 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_r = 724.30
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.078
wR(F²) = 0.224
S = 1.07
3592 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.91	1.80	2.696 (6)	169
C4—H4⋯O2ⁱⁱ	0.98	2.35	3.306 (9)	163
Symmetry codes: (i) x-1, y, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902426X/rz2338sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902426X/rz2338Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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 diffraction analysis were obtained by slow evaporation of the solution at room temperature after 5 days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: 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).

Figures top

	Fig. 1. The structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Atoms labelled with the suffix A are generated by the symmetry operator (-x, 1-y, 1-z). Only one component of the disordered methyl group is shown.
	Fig. 2. Packing diagram of the title compound viewed along the c axis. Intermolecular hydrogen bonds are shown as dashed lines. Only one component of the disordered methyl group is shown.

1,4-Diferrocenyl-2-methylpiperazine-1,4-diium bis(trifluoroacetate) top

Crystal data top

[Fe₂(C₅H₅)₂(C₁₇H₂₄N₂)](C₂F₃O₂)₂	F(000) = 744.0
M_r = 724.30	D_x = 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

Data collection top

Rigaku SCXmini diffractometer	3592 independent reflections
Radiation source: fine-focus sealed tube	3117 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.771, T_max = 0.819	l = −17→17
15611 measured reflections

Refinement top

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(F_o²) + (0.1088P)² + 3.5578P] where P = (F_o² + 2F_c²)/3
3592 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 1.06 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Fe₂(C₅H₅)₂(C₁₇H₂₄N₂)](C₂F₃O₂)₂	V = 1567.7 (7) Å³
M_r = 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)°

Data collection top

Rigaku SCXmini diffractometer	3592 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3117 reflections with I > 2σ(I)
T_min = 0.771, T_max = 0.819	R_int = 0.042
15611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	0 restraints
wR(F²) = 0.224	H-atom parameters constrained
S = 1.07	Δρ_max = 1.06 e Å⁻³
3592 reflections	Δρ_min = −0.71 e Å⁻³
209 parameters

Special details top

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	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.771, 0.819
No. of measured, independent and observed [I > 2σ(I)] reflections	15611, 3592, 3117
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.71

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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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