1-[(2,3,4,5,6-Penta­fluoro­phen­yl)ethyn­yl]ferrocene

Zhang, C.; Zhang, H.; Dai, D.; Liang, J.

doi:10.1107/S1600536810026772

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m914

https://doi.org/10.1107/S1600536810026772

Open

access

1-[(2,3,4,5,6-Pentafluorophenyl)ethynyl]ferrocene

Chan Zhang,^a ^* Honglin Zhang,^a Dongdong Dai ^a and Jinhua Liang ^a

^aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: zhangchan20050333@163.com

(Received 29 June 2010; accepted 6 July 2010; online 10 July 2010)

The molecular structure of the title compound, [Fe(C₅H₅)(C₁₃H₄F₅)], consists of a ferrocenyl group and a 2,3,4,5,6-pentafluorobenzene group linked through an ethyne spacer. The crystal packing is dominated by intermolecular C—H⋯F hydrogen bonds, C—F⋯π interactions between the pentafluorobenzene groups [F⋯centroid distances = 3.882 (2) and 3.884 (2) Å] and π–π interactions between the pentafluorobenzene and cyclopentadienyl rings [centroid–centroid distance = 3.741 (1) Å].

Related literature

For general background to ferrocene derivatives, see: Debroy & Roy (2007 ). For a related structure, see: Valdebenito et al. (2010 ). For the synthesis, see: Torres et al. (2002 ); Zora et al. (2006 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₃H₄F₅)]
M_r = 376.10
Triclinic, $[P \overline 1]$
a = 6.0767 (9) Å
b = 10.7164 (15) Å
c = 12.6014 (18) Å
α = 65.725 (2)°
β = 89.364 (3)°
γ = 78.726 (2)°
V = 731.41 (18) Å³
Z = 2
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 292 K
0.30 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX CCD diffractometer
4793 measured reflections
2533 independent reflections
2169 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.05
2533 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯F5ⁱ	0.93	2.50	3.176 (3)	130
Symmetry code: (i) -x+1, -y+2, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810026772/hy2327sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026772/hy2327Isup2.hkl

checkCIF report

Comment top

Ferrocene derivatives with linear, unsaturated side-arms show altered unique properties, such as electrical conductivity, thermal stability, magnetic, electronic, redox and non-linear optical behaviors, compared to their saturated derivatives (Debroy & Roy, 2007).

The molecular structure of the title compound is composed of a ferrocenyl group and a pentafluorobenzene group joined by an organic ethyne spacer. Two cyclopentadienyl rings of the ferrocenyl group are parallel (Valdebenito et al., 2010). The main features of the structure are an intermolecular C—H···F hydrogen bond between the ferrocenyl and pentafluorobenzene (Table 1), C—F···π interactions between the pentafluorobenzene groups [F···centroid distances = 3.882 (2) and 3.884 (2) Å] and a π–π interaction between the pentafluorobenzene and cyclopentadienyl rings [centroid–centroid distance = 3.741 (1) Å].

Related literature top

For general background to ferrocene derivatives, see: Debroy & Roy (2007). For a related structure, see: Valdebenito et al. (2010). For the synthesis, see: Torres et al. (2002); Zora et al. (2006).

Experimental top

The title compound was synthesized according to a modified literature procedure (Torres et al., 2002; Zora et al., 2006). 1,2,3,4,5-Pentafluoro-6-iodobenzene (735 mg, 2.5 mmol) and ethynylferrocene (525 mg, 2.5 mmol) were added to a mixture of Cu(CH₃CO₂)₂ (40 mg, 0.2 mmol), Pd(PPh₃)₂Cl₂ (140 mg, 0.2 mmol) and ⁱPr₂NH (30 ml) under argon. The resulting mixture was refluxed at 365 K for 18 h. The solution was then extracted with dichloromethane, washed with water and dried over Na₂SO₄. Final purification was achieved by flash column chromatography on silica gel using dichloromethane/petroleum (1:4) as eluant. The product was obtained in 30% yield. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution of the compound in dichloromethane/hexane (1:10 v/v) at room temperature.

Structure description top

For general background to ferrocene derivatives, see: Debroy & Roy (2007). For a related structure, see: Valdebenito et al. (2010). For the synthesis, see: Torres et al. (2002); Zora et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

1-[(2,3,4,5,6-Pentafluorophenyl)ethynyl]ferrocene top

Crystal data top

[Fe(C₅H₅)(C₁₃H₄F₅)]	Z = 2
M_r = 376.10	F(000) = 376
Triclinic, P1	D_x = 1.708 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0767 (9) Å	Cell parameters from 1760 reflections
b = 10.7164 (15) Å	θ = 3.3–25.1°
c = 12.6014 (18) Å	µ = 1.08 mm⁻¹
α = 65.725 (2)°	T = 292 K
β = 89.364 (3)°	Plate, yellow
γ = 78.726 (2)°	0.30 × 0.04 × 0.02 mm
V = 731.41 (18) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	2169 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
φ and ω scans	h = −7→7
4793 measured reflections	k = −12→12
2533 independent reflections	l = −13→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0602P)² + 0.0784P] where P = (F_o² + 2F_c²)/3
2533 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₃H₄F₅)]	γ = 78.726 (2)°
M_r = 376.10	V = 731.41 (18) Å³
Triclinic, P1	Z = 2
a = 6.0767 (9) Å	Mo Kα radiation
b = 10.7164 (15) Å	µ = 1.08 mm⁻¹
c = 12.6014 (18) Å	T = 292 K
α = 65.725 (2)°	0.30 × 0.04 × 0.02 mm
β = 89.364 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	2169 reflections with I > 2σ(I)
4793 measured reflections	R_int = 0.021
2533 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	Δρ_max = 0.41 e Å⁻³
2533 reflections	Δρ_min = −0.25 e Å⁻³
217 parameters

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

	x	y	z	U_iso*/U_eq
Fe1	0.72848 (6)	0.78028 (4)	0.74835 (3)	0.03952 (17)
C1	0.7513 (5)	0.5868 (3)	0.8801 (3)	0.0544 (8)
H1	0.7967	0.5607	0.9578	0.065*
C2	0.8930 (6)	0.5793 (3)	0.7932 (3)	0.0603 (9)
H2	1.0483	0.5472	0.8031	0.072*
C3	0.7575 (6)	0.6290 (3)	0.6885 (3)	0.0629 (9)
H3	0.8079	0.6360	0.6167	0.075*
C4	0.5318 (5)	0.6666 (3)	0.7110 (3)	0.0550 (8)
H4	0.4074	0.7022	0.6570	0.066*
C5	0.5292 (5)	0.6405 (3)	0.8295 (3)	0.0534 (8)
H5	0.4024	0.6561	0.8679	0.064*
C6	0.8628 (5)	0.8977 (3)	0.8131 (3)	0.0466 (7)
C7	0.9602 (5)	0.9037 (3)	0.7080 (3)	0.0537 (8)
H7	1.1120	0.8756	0.7001	0.064*
C8	0.7850 (6)	0.9598 (3)	0.6182 (3)	0.0612 (9)
H8	0.8017	0.9753	0.5406	0.073*
C9	0.5823 (6)	0.9883 (3)	0.6656 (3)	0.0620 (9)
H9	0.4417	1.0264	0.6245	0.074*
C10	0.6256 (5)	0.9498 (3)	0.7858 (3)	0.0535 (8)
H10	0.5195	0.9569	0.8379	0.064*
C11	0.9780 (5)	0.8492 (3)	0.9247 (3)	0.0506 (7)
C12	1.0717 (5)	0.8129 (3)	1.0184 (3)	0.0524 (7)
C13	1.1670 (5)	0.7703 (3)	1.1340 (2)	0.0434 (6)
C14	1.3917 (5)	0.7049 (3)	1.1689 (2)	0.0441 (7)
C15	1.4796 (5)	0.6621 (3)	1.2811 (3)	0.0496 (7)
C16	1.3452 (6)	0.6841 (3)	1.3614 (2)	0.0539 (8)
C17	1.1218 (6)	0.7482 (3)	1.3302 (3)	0.0551 (8)
C18	1.0362 (5)	0.7906 (3)	1.2187 (3)	0.0518 (8)
F1	1.5272 (3)	0.68281 (19)	1.09132 (16)	0.0650 (5)
F2	1.6961 (3)	0.59629 (19)	1.31194 (17)	0.0709 (5)
F3	1.4306 (4)	0.6459 (2)	1.46997 (16)	0.0892 (7)
F4	0.9884 (4)	0.7688 (2)	1.40989 (18)	0.0896 (7)
F5	0.8196 (3)	0.85479 (19)	1.19000 (19)	0.0741 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0398 (3)	0.0418 (3)	0.0403 (3)	−0.01159 (17)	0.00257 (18)	−0.01908 (19)
C1	0.067 (2)	0.0416 (15)	0.0485 (18)	−0.0124 (14)	−0.0050 (16)	−0.0118 (14)
C2	0.0542 (19)	0.0474 (17)	0.085 (3)	−0.0053 (14)	0.0022 (18)	−0.0358 (17)
C3	0.085 (2)	0.0606 (19)	0.065 (2)	−0.0260 (17)	0.0217 (19)	−0.0425 (18)
C4	0.0571 (19)	0.0602 (18)	0.060 (2)	−0.0209 (15)	−0.0019 (16)	−0.0336 (16)
C5	0.0535 (19)	0.0519 (17)	0.059 (2)	−0.0222 (14)	0.0127 (16)	−0.0228 (15)
C6	0.0520 (18)	0.0408 (14)	0.0502 (17)	−0.0126 (12)	−0.0047 (14)	−0.0207 (13)
C7	0.0466 (17)	0.0569 (17)	0.057 (2)	−0.0210 (14)	0.0025 (15)	−0.0188 (15)
C8	0.069 (2)	0.0617 (19)	0.0443 (18)	−0.0308 (17)	−0.0013 (16)	−0.0060 (15)
C9	0.056 (2)	0.0463 (17)	0.071 (2)	−0.0078 (14)	−0.0208 (17)	−0.0127 (16)
C10	0.0512 (18)	0.0439 (15)	0.067 (2)	−0.0031 (13)	−0.0014 (15)	−0.0278 (15)
C11	0.0554 (19)	0.0433 (15)	0.0563 (19)	−0.0155 (13)	−0.0044 (15)	−0.0215 (14)
C12	0.0585 (19)	0.0470 (16)	0.055 (2)	−0.0173 (14)	−0.0031 (16)	−0.0210 (15)
C13	0.0499 (17)	0.0384 (14)	0.0460 (16)	−0.0157 (12)	0.0008 (13)	−0.0188 (13)
C14	0.0471 (17)	0.0444 (14)	0.0464 (17)	−0.0138 (12)	0.0086 (14)	−0.0228 (13)
C15	0.0514 (18)	0.0406 (15)	0.0554 (19)	−0.0124 (13)	−0.0034 (15)	−0.0173 (14)
C16	0.085 (2)	0.0417 (15)	0.0356 (16)	−0.0192 (15)	−0.0014 (16)	−0.0136 (13)
C17	0.080 (2)	0.0444 (16)	0.0496 (19)	−0.0222 (15)	0.0240 (17)	−0.0240 (14)
C18	0.0484 (18)	0.0395 (15)	0.068 (2)	−0.0123 (13)	0.0092 (16)	−0.0218 (15)
F1	0.0653 (12)	0.0744 (11)	0.0630 (11)	−0.0143 (9)	0.0201 (9)	−0.0366 (10)
F2	0.0557 (12)	0.0658 (11)	0.0808 (13)	−0.0075 (9)	−0.0152 (10)	−0.0222 (10)
F3	0.147 (2)	0.0710 (12)	0.0463 (11)	−0.0216 (13)	−0.0146 (12)	−0.0211 (10)
F4	0.1264 (19)	0.0795 (13)	0.0750 (13)	−0.0281 (12)	0.0557 (13)	−0.0424 (11)
F5	0.0497 (11)	0.0640 (11)	0.1014 (15)	−0.0069 (9)	0.0147 (10)	−0.0299 (11)

Geometric parameters (Å, º) top

Fe1—C3	2.029 (3)	C6—C10	1.430 (4)
Fe1—C2	2.032 (3)	C7—C8	1.411 (4)
Fe1—C1	2.034 (3)	C7—H7	0.9300
Fe1—C7	2.037 (3)	C8—C9	1.398 (4)
Fe1—C8	2.040 (3)	C8—H8	0.9300
Fe1—C10	2.042 (3)	C9—C10	1.409 (4)
Fe1—C5	2.044 (3)	C9—H9	0.9300
Fe1—C6	2.044 (3)	C10—H10	0.9300
Fe1—C9	2.045 (3)	C11—C12	1.191 (4)
Fe1—C4	2.047 (3)	C12—C13	1.427 (4)
C1—C2	1.404 (4)	C13—C18	1.386 (4)
C1—C5	1.405 (4)	C13—C14	1.391 (4)
C1—H1	0.9300	C14—F1	1.336 (3)
C2—C3	1.406 (5)	C14—C15	1.372 (4)
C2—H2	0.9300	C15—F2	1.342 (3)
C3—C4	1.412 (4)	C15—C16	1.360 (4)
C3—H3	0.9300	C16—F3	1.335 (3)
C4—C5	1.402 (4)	C16—C17	1.376 (5)
C4—H4	0.9300	C17—F4	1.345 (3)
C5—H5	0.9300	C17—C18	1.360 (4)
C6—C11	1.421 (4)	C18—F5	1.337 (3)
C6—C7	1.426 (4)

C3—Fe1—C2	40.51 (13)	C5—C4—C3	107.6 (3)
C3—Fe1—C1	67.85 (13)	C5—C4—Fe1	69.83 (16)
C2—Fe1—C1	40.41 (12)	C3—C4—Fe1	69.08 (17)
C3—Fe1—C7	118.88 (13)	C5—C4—H4	126.2
C2—Fe1—C7	108.34 (13)	C3—C4—H4	126.2
C1—Fe1—C7	128.23 (13)	Fe1—C4—H4	126.4
C3—Fe1—C8	109.38 (14)	C4—C5—C1	108.2 (3)
C2—Fe1—C8	129.09 (14)	C4—C5—Fe1	70.07 (16)
C1—Fe1—C8	166.63 (13)	C1—C5—Fe1	69.47 (16)
C7—Fe1—C8	40.51 (12)	C4—C5—H5	125.9
C3—Fe1—C10	166.11 (14)	C1—C5—H5	125.9
C2—Fe1—C10	151.56 (14)	Fe1—C5—H5	126.1
C1—Fe1—C10	117.85 (13)	C11—C6—C7	126.8 (3)
C7—Fe1—C10	68.73 (12)	C11—C6—C10	125.8 (3)
C8—Fe1—C10	68.07 (14)	C7—C6—C10	107.4 (3)
C3—Fe1—C5	67.75 (13)	C11—C6—Fe1	126.48 (19)
C2—Fe1—C5	67.92 (13)	C7—C6—Fe1	69.29 (15)
C1—Fe1—C5	40.30 (12)	C10—C6—Fe1	69.44 (16)
C7—Fe1—C5	165.96 (12)	C8—C7—C6	107.7 (3)
C8—Fe1—C5	152.15 (13)	C8—C7—Fe1	69.85 (17)
C10—Fe1—C5	107.70 (13)	C6—C7—Fe1	69.79 (16)
C3—Fe1—C6	152.12 (14)	C8—C7—H7	126.1
C2—Fe1—C6	117.98 (13)	C6—C7—H7	126.1
C1—Fe1—C6	107.64 (12)	Fe1—C7—H7	125.8
C7—Fe1—C6	40.92 (11)	C9—C8—C7	108.5 (3)
C8—Fe1—C6	68.29 (13)	C9—C8—Fe1	70.17 (17)
C10—Fe1—C6	40.98 (11)	C7—C8—Fe1	69.64 (17)
C5—Fe1—C6	127.66 (12)	C9—C8—H8	125.8
C3—Fe1—C9	129.10 (14)	C7—C8—H8	125.8
C2—Fe1—C9	166.84 (14)	Fe1—C8—H8	126.0
C1—Fe1—C9	151.75 (14)	C8—C9—C10	108.9 (3)
C7—Fe1—C9	67.90 (13)	C8—C9—Fe1	69.80 (18)
C8—Fe1—C9	40.03 (13)	C10—C9—Fe1	69.72 (16)
C10—Fe1—C9	40.35 (12)	C8—C9—H9	125.5
C5—Fe1—C9	118.81 (13)	C10—C9—H9	125.5
C6—Fe1—C9	68.10 (12)	Fe1—C9—H9	126.5
C3—Fe1—C4	40.53 (13)	C9—C10—C6	107.4 (3)
C2—Fe1—C4	68.12 (13)	C9—C10—Fe1	69.93 (17)
C1—Fe1—C4	67.74 (13)	C6—C10—Fe1	69.58 (15)
C7—Fe1—C4	152.61 (13)	C9—C10—H10	126.3
C8—Fe1—C4	119.34 (13)	C6—C10—H10	126.3
C10—Fe1—C4	127.70 (12)	Fe1—C10—H10	125.8
C5—Fe1—C4	40.10 (12)	C12—C11—C6	177.7 (3)
C6—Fe1—C4	165.50 (12)	C11—C12—C13	175.5 (3)
C9—Fe1—C4	109.02 (13)	C18—C13—C14	116.4 (3)
C2—C1—C5	108.3 (3)	C18—C13—C12	120.9 (3)
C2—C1—Fe1	69.73 (17)	C14—C13—C12	122.7 (3)
C5—C1—Fe1	70.23 (16)	F1—C14—C15	118.6 (3)
C2—C1—H1	125.8	F1—C14—C13	119.4 (3)
C5—C1—H1	125.8	C15—C14—C13	122.0 (3)
Fe1—C1—H1	125.8	F2—C15—C16	120.2 (3)
C1—C2—C3	107.6 (3)	F2—C15—C14	120.1 (3)
C1—C2—Fe1	69.86 (16)	C16—C15—C14	119.6 (3)
C3—C2—Fe1	69.65 (17)	F3—C16—C15	120.0 (3)
C1—C2—H2	126.2	F3—C16—C17	119.9 (3)
C3—C2—H2	126.2	C15—C16—C17	120.0 (3)
Fe1—C2—H2	125.9	F4—C17—C18	120.1 (3)
C2—C3—C4	108.3 (3)	F4—C17—C16	120.0 (3)
C2—C3—Fe1	69.84 (17)	C18—C17—C16	119.9 (3)
C4—C3—Fe1	70.39 (17)	F5—C18—C17	118.8 (3)
C2—C3—H3	125.8	F5—C18—C13	119.2 (3)
C4—C3—H3	125.8	C17—C18—C13	122.0 (3)
Fe1—C3—H3	125.5

C3—Fe1—C1—C2	37.99 (19)	C1—Fe1—C6—C10	−112.43 (19)
C7—Fe1—C1—C2	−72.1 (2)	C7—Fe1—C6—C10	118.9 (3)
C8—Fe1—C1—C2	−42.6 (6)	C8—Fe1—C6—C10	81.1 (2)
C10—Fe1—C1—C2	−155.99 (19)	C5—Fe1—C6—C10	−72.4 (2)
C5—Fe1—C1—C2	119.2 (3)	C9—Fe1—C6—C10	37.84 (18)
C6—Fe1—C1—C2	−112.7 (2)	C4—Fe1—C6—C10	−43.4 (5)
C9—Fe1—C1—C2	170.9 (2)	C11—C6—C7—C8	−179.5 (3)
C4—Fe1—C1—C2	81.9 (2)	C10—C6—C7—C8	0.6 (3)
C3—Fe1—C1—C5	−81.3 (2)	Fe1—C6—C7—C8	59.8 (2)
C2—Fe1—C1—C5	−119.2 (3)	C11—C6—C7—Fe1	120.7 (3)
C7—Fe1—C1—C5	168.67 (17)	C10—C6—C7—Fe1	−59.20 (19)
C8—Fe1—C1—C5	−161.9 (5)	C3—Fe1—C7—C8	86.4 (2)
C10—Fe1—C1—C5	84.8 (2)	C2—Fe1—C7—C8	129.4 (2)
C6—Fe1—C1—C5	128.05 (18)	C1—Fe1—C7—C8	169.92 (19)
C9—Fe1—C1—C5	51.7 (3)	C10—Fe1—C7—C8	−80.7 (2)
C4—Fe1—C1—C5	−37.32 (18)	C5—Fe1—C7—C8	−158.5 (4)
C5—C1—C2—C3	0.2 (3)	C6—Fe1—C7—C8	−118.8 (3)
Fe1—C1—C2—C3	−59.7 (2)	C9—Fe1—C7—C8	−37.2 (2)
C5—C1—C2—Fe1	59.9 (2)	C4—Fe1—C7—C8	51.7 (4)
C3—Fe1—C2—C1	−118.6 (3)	C3—Fe1—C7—C6	−154.81 (18)
C7—Fe1—C2—C1	128.06 (19)	C2—Fe1—C7—C6	−111.85 (19)
C8—Fe1—C2—C1	168.36 (18)	C1—Fe1—C7—C6	−71.3 (2)
C10—Fe1—C2—C1	49.0 (3)	C8—Fe1—C7—C6	118.8 (3)
C5—Fe1—C2—C1	−37.52 (18)	C10—Fe1—C7—C6	38.03 (17)
C6—Fe1—C2—C1	84.6 (2)	C5—Fe1—C7—C6	−39.7 (6)
C9—Fe1—C2—C1	−160.8 (5)	C9—Fe1—C7—C6	81.60 (19)
C4—Fe1—C2—C1	−80.9 (2)	C4—Fe1—C7—C6	170.5 (2)
C1—Fe1—C2—C3	118.6 (3)	C6—C7—C8—C9	−0.1 (3)
C7—Fe1—C2—C3	−113.3 (2)	Fe1—C7—C8—C9	59.6 (2)
C8—Fe1—C2—C3	−73.0 (2)	C6—C7—C8—Fe1	−59.75 (19)
C10—Fe1—C2—C3	167.7 (2)	C3—Fe1—C8—C9	128.4 (2)
C5—Fe1—C2—C3	81.1 (2)	C2—Fe1—C8—C9	169.54 (19)
C6—Fe1—C2—C3	−156.79 (19)	C1—Fe1—C8—C9	−156.0 (5)
C9—Fe1—C2—C3	−42.2 (6)	C7—Fe1—C8—C9	−119.5 (3)
C4—Fe1—C2—C3	37.74 (18)	C10—Fe1—C8—C9	−37.05 (19)
C1—C2—C3—C4	−0.3 (3)	C5—Fe1—C8—C9	49.5 (4)
Fe1—C2—C3—C4	−60.1 (2)	C6—Fe1—C8—C9	−81.4 (2)
C1—C2—C3—Fe1	59.8 (2)	C4—Fe1—C8—C9	85.0 (2)
C1—Fe1—C3—C2	−37.89 (19)	C3—Fe1—C8—C7	−112.1 (2)
C7—Fe1—C3—C2	84.7 (2)	C2—Fe1—C8—C7	−70.9 (2)
C8—Fe1—C3—C2	128.1 (2)	C1—Fe1—C8—C7	−36.5 (6)
C10—Fe1—C3—C2	−155.0 (5)	C10—Fe1—C8—C7	82.5 (2)
C5—Fe1—C3—C2	−81.6 (2)	C5—Fe1—C8—C7	169.0 (2)
C6—Fe1—C3—C2	48.1 (3)	C6—Fe1—C8—C7	38.17 (19)
C9—Fe1—C3—C2	168.64 (19)	C9—Fe1—C8—C7	119.5 (3)
C4—Fe1—C3—C2	−119.1 (3)	C4—Fe1—C8—C7	−155.52 (19)
C2—Fe1—C3—C4	119.1 (3)	C7—C8—C9—C10	−0.4 (4)
C1—Fe1—C3—C4	81.2 (2)	Fe1—C8—C9—C10	58.9 (2)
C7—Fe1—C3—C4	−156.23 (18)	C7—C8—C9—Fe1	−59.3 (2)
C8—Fe1—C3—C4	−112.8 (2)	C3—Fe1—C9—C8	−72.4 (2)
C10—Fe1—C3—C4	−35.9 (6)	C2—Fe1—C9—C8	−38.2 (6)
C5—Fe1—C3—C4	37.50 (18)	C1—Fe1—C9—C8	168.5 (2)
C6—Fe1—C3—C4	167.2 (2)	C7—Fe1—C9—C8	37.59 (19)
C9—Fe1—C3—C4	−72.3 (2)	C10—Fe1—C9—C8	120.3 (3)
C2—C3—C4—C5	0.3 (3)	C5—Fe1—C9—C8	−156.08 (19)
Fe1—C3—C4—C5	−59.5 (2)	C6—Fe1—C9—C8	81.9 (2)
C2—C3—C4—Fe1	59.8 (2)	C4—Fe1—C9—C8	−113.3 (2)
C3—Fe1—C4—C5	119.0 (3)	C3—Fe1—C9—C10	167.30 (18)
C2—Fe1—C4—C5	81.3 (2)	C2—Fe1—C9—C10	−158.5 (5)
C1—Fe1—C4—C5	37.50 (18)	C1—Fe1—C9—C10	48.2 (3)
C7—Fe1—C4—C5	169.1 (2)	C7—Fe1—C9—C10	−82.72 (19)
C8—Fe1—C4—C5	−155.12 (19)	C8—Fe1—C9—C10	−120.3 (3)
C10—Fe1—C4—C5	−71.3 (2)	C5—Fe1—C9—C10	83.6 (2)
C6—Fe1—C4—C5	−36.5 (5)	C6—Fe1—C9—C10	−38.43 (18)
C9—Fe1—C4—C5	−112.5 (2)	C4—Fe1—C9—C10	126.40 (19)
C2—Fe1—C4—C3	−37.72 (19)	C8—C9—C10—C6	0.8 (3)
C1—Fe1—C4—C3	−81.5 (2)	Fe1—C9—C10—C6	59.73 (19)
C7—Fe1—C4—C3	50.1 (4)	C8—C9—C10—Fe1	−58.9 (2)
C8—Fe1—C4—C3	85.9 (2)	C11—C6—C10—C9	179.2 (3)
C10—Fe1—C4—C3	169.76 (19)	C7—C6—C10—C9	−0.8 (3)
C5—Fe1—C4—C3	−119.0 (3)	Fe1—C6—C10—C9	−60.0 (2)
C6—Fe1—C4—C3	−155.5 (4)	C11—C6—C10—Fe1	−120.8 (3)
C9—Fe1—C4—C3	128.6 (2)	C7—C6—C10—Fe1	59.11 (19)
C3—C4—C5—C1	−0.2 (3)	C3—Fe1—C10—C9	−45.3 (6)
Fe1—C4—C5—C1	−59.2 (2)	C2—Fe1—C10—C9	169.9 (2)
C3—C4—C5—Fe1	59.0 (2)	C1—Fe1—C10—C9	−156.46 (19)
C2—C1—C5—C4	0.0 (3)	C7—Fe1—C10—C9	80.5 (2)
Fe1—C1—C5—C4	59.6 (2)	C8—Fe1—C10—C9	36.76 (19)
C2—C1—C5—Fe1	−59.6 (2)	C5—Fe1—C10—C9	−113.9 (2)
C3—Fe1—C5—C4	−37.89 (19)	C6—Fe1—C10—C9	118.5 (3)
C2—Fe1—C5—C4	−81.8 (2)	C4—Fe1—C10—C9	−74.1 (2)
C1—Fe1—C5—C4	−119.4 (3)	C3—Fe1—C10—C6	−163.8 (5)
C7—Fe1—C5—C4	−158.9 (5)	C2—Fe1—C10—C6	51.5 (3)
C8—Fe1—C5—C4	51.7 (3)	C1—Fe1—C10—C6	85.1 (2)
C10—Fe1—C5—C4	128.14 (19)	C7—Fe1—C10—C6	−37.97 (17)
C6—Fe1—C5—C4	169.15 (17)	C8—Fe1—C10—C6	−81.69 (19)
C9—Fe1—C5—C4	85.7 (2)	C5—Fe1—C10—C6	127.62 (18)
C3—Fe1—C5—C1	81.5 (2)	C9—Fe1—C10—C6	−118.5 (3)
C2—Fe1—C5—C1	37.61 (19)	C4—Fe1—C10—C6	167.43 (17)
C7—Fe1—C5—C1	−39.5 (6)	C18—C13—C14—F1	−179.7 (2)
C8—Fe1—C5—C1	171.1 (3)	C12—C13—C14—F1	1.4 (4)
C10—Fe1—C5—C1	−112.45 (19)	C18—C13—C14—C15	0.2 (4)
C6—Fe1—C5—C1	−71.4 (2)	C12—C13—C14—C15	−178.7 (3)
C9—Fe1—C5—C1	−154.93 (19)	F1—C14—C15—F2	−1.7 (4)
C4—Fe1—C5—C1	119.4 (3)	C13—C14—C15—F2	178.4 (2)
C3—Fe1—C6—C11	−68.3 (4)	F1—C14—C15—C16	179.7 (2)
C2—Fe1—C6—C11	−35.1 (3)	C13—C14—C15—C16	−0.2 (4)
C1—Fe1—C6—C11	7.5 (3)	F2—C15—C16—F3	3.0 (4)
C7—Fe1—C6—C11	−121.1 (3)	C14—C15—C16—F3	−178.4 (2)
C8—Fe1—C6—C11	−158.9 (3)	F2—C15—C16—C17	−178.2 (2)
C10—Fe1—C6—C11	120.0 (3)	C14—C15—C16—C17	0.4 (4)
C5—Fe1—C6—C11	47.6 (3)	F3—C16—C17—F4	−1.9 (4)
C9—Fe1—C6—C11	157.8 (3)	C15—C16—C17—F4	179.4 (3)
C4—Fe1—C6—C11	76.5 (5)	F3—C16—C17—C18	178.2 (2)
C3—Fe1—C6—C7	52.8 (3)	C15—C16—C17—C18	−0.6 (4)
C2—Fe1—C6—C7	86.0 (2)	F4—C17—C18—F5	1.2 (4)
C1—Fe1—C6—C7	128.66 (18)	C16—C17—C18—F5	−178.9 (2)
C8—Fe1—C6—C7	−37.81 (19)	F4—C17—C18—C13	−179.3 (2)
C10—Fe1—C6—C7	−118.9 (3)	C16—C17—C18—C13	0.6 (4)
C5—Fe1—C6—C7	168.71 (17)	C14—C13—C18—F5	179.1 (2)
C9—Fe1—C6—C7	−81.1 (2)	C12—C13—C18—F5	−2.0 (4)
C4—Fe1—C6—C7	−162.3 (4)	C14—C13—C18—C17	−0.4 (4)
C3—Fe1—C6—C10	171.8 (2)	C12—C13—C18—C17	178.5 (3)
C2—Fe1—C6—C10	−155.05 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···F5ⁱ	0.93	2.50	3.176 (3)	130

Symmetry code: (i) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₃H₄F₅)]
M_r	376.10
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	6.0767 (9), 10.7164 (15), 12.6014 (18)
α, β, γ (°)	65.725 (2), 89.364 (3), 78.726 (2)
V (Å³)	731.41 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.30 × 0.04 × 0.02

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4793, 2533, 2169
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.05
No. of reflections	2533
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.25

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
C10—H10···F5ⁱ	0.93	2.50	3.176 (3)	130

Symmetry code: (i) −x+1, −y+2, −z+2.

Acknowledgements

The authors are grateful to Mr Xianggao Meng for the data collection.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Debroy, P. & Roy, S. (2007). Coord. Chem. Rev. 251, 203–221. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Torres, J. C., Pilli, R. A., Vargas, M. D., Violante, F. A., Garden, S. J. & Pinto, A. C. (2002). Tetrahedron, 58, 4487–4492. Web of Science CrossRef CAS Google Scholar
Valdebenito, C., Garland, M. T., Fuentealba, M. & Escobar, C. A. (2010). Acta Cryst. E66, m838. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zora, M., Açıkgöz, C., Tumay, T. A., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327–m330. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar