1-Ferrocenyl-3-(3-fluoro­anilino)propan-1-one

Leka, Z.; Novaković, S.B.; Pejović, A.; Bogdanović, G.A.; Vukićević, R.D.

doi:10.1107/S1600536812003510

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m231

doi:10.1107/S1600536812003510

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1-Ferrocenyl-3-(3-fluoroanilino)propan-1-one

Zorica Leka,^a ^* Sladjana B. Novaković,^b Anka Pejović,^c Goran A. Bogdanović ^b and Rastko D. Vukićević ^c

^aFaculty of Metallurgy and Technology, University of Montenegro, Cetinjski put bb, 81000 Podgorica, Montenegro, ^b'Vinča' Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, PO Box 522, 11001 Belgrade, Serbia, and ^cDepartment of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovića 12, 34000 Kragujevac, Serbia
^*Correspondence e-mail: zorica@ac.me

(Received 18 January 2012; accepted 26 January 2012; online 31 January 2012)

The title ferrocene derivative, [Fe(C₅H₅)(C₁₄H₁₃FNO)], crystallizes in the same space group with similar unit-cell parameters as the derivatives 3-anilino-1-ferrocenylpropan-1-one [Leka et al. (2012 ). Acta Cryst. E68, m229] and 1-ferrocenyl-3-(4-methylanilino)propan-1-one [Leka et al. (2012 ). Acta Cryst. E68, m230]. The dihedral angle between the best planes of the benzene ring and the substituted cyclopentadienyl ring is 83.4 (1)°. The presence of the electronegative fluoro substituent in the meta position of the aniline group does not alter the crystal packing compared to the other two derivatives. The molecules are connected into centrosymmetric dimers via N—H⋯O hydrogen bonds. In addition, C—H⋯O and C—H⋯N contacts stabilize the crystal packing.

Related literature

For the physico-chemical properties of ferrocene-based compounds see: Togni & Hayashi (1995 ). For related crystal structures and details of the synthesis see: Damljanović et al. (2011 ); Stevanović et al. (2012 ); Leka et al. (2012a,b).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₄H₁₃FNO)]
M_r = 351.19
Triclinic, $[P \overline 1]$
a = 7.6602 (4) Å
b = 9.6438 (4) Å
c = 12.0626 (6) Å
α = 86.548 (4)°
β = 73.590 (4)°
γ = 69.138 (4)°
V = 797.95 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 293 K
0.30 × 0.24 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.892, T_max = 1.000
6470 measured reflections
3637 independent reflections
2733 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.102
S = 1.06
3637 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.83 (3)	2.24 (3)	3.049 (3)	165 (3)
C19—H19⋯O1ⁱ	0.93	2.57	3.342 (3)	141
C4—H4⋯N1ⁱⁱ	0.93	2.66	3.517 (3)	153
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and POV-RAY (Persistence of Vision, 2004 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ), PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812003510/bt5792sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003510/bt5792Isup2.hkl

checkCIF report

Comment top

As a continuation of our research related to ferrocene containing Mannich bases, we analyzed the crystal structure of 1-Ferrocenyl-3-(3-fluorophenylamino)propan-1-one (I). The present compound (Figure 1) exhibits the pronounced similarity to the previous ones, either in bond lengths and angles as well as in molecular conformation. The mutual orientation of the cyclopentadienyl (Cp) rings within the Fc unit, given by the smallest torsion angle C—Cg1—Cg2—C of 4.5° is close to eclipsed one, with small mutual twisting as in the case of 1-Ferrocenyl-3-(phenylamino)propan-1-one (Leka et al., 2012a) and 1- Ferrocenyl-3-(p-tolylamino)propan-1-one (Leka et al., 2012b).

The Cp rings are almost parallel forming the dihedral angle between the Cp ring planes of 1.3 (2)°, while the distances of Fe1 to Cg1 and Cg2 centroids are 1.64 and 1.65 Å, respectively. In accordance with previously observed trend the Fe1···Cg distances toward the substituted Cp ring are 0.01 Å shorter than those toward the unsubstituted ring. The torsion angles within the most flexible, aliphatic part of the molecule (C1—C11—C12—C13—N1) indicate a molecular conformation similar to the previously reported derivatives. The dihedral angle between the best planes of Cp1 and phenyl ring is 83.4 (1)°. It is worth noticing that the presence of the electronegative fuloro substituent on the phenylamino moiety has no influence on the molecule arrangement (Fig. 2), in fact F atom do not participate in any interaction. The closest donor, the cyclopentadienyl C7—H fragment is placed at the distance of 2.69 Å. Molecules exhibit arrangement which is very similar to those observed in phenylamino (Leka et al., 2012a) and tolylamino (Leka et al., 2012b) derivatives.

Related literature top

For the physico-chemical properties of ferrocene-based compounds see: Togni & Hayashi (1995). For related crystal structures and details of the synthesis see: Damljanović et al. (2011); Stevanović et al. (2012); Leka et al. (2012a,b).

Experimental top

The compound was obtained by an aza-Michael addition of the corresponding arylamine to acryloylferrocene. The reaction was performed by microwave (MW) irradiation (500 W/5 min) of a mixture of reactants and montmorillonite K-10, without a solvent as described by Damljanović et al. (2011).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and POV-RAY (Persistence of Vision, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 40% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The segment of crystal packing showing the interconnection of the dimers into a chain.

1-Ferrocenyl-3-(3-fluoroanilino)propan-1-one top

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₃FNO)]	Z = 2
M_r = 351.19	F(000) = 364
Triclinic, P1	D_x = 1.462 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6602 (4) Å	Cell parameters from 2586 reflections
b = 9.6438 (4) Å	θ = 3.0–29.0°
c = 12.0626 (6) Å	µ = 0.96 mm⁻¹
α = 86.548 (4)°	T = 293 K
β = 73.590 (4)°	Prismatic, orange
γ = 69.138 (4)°	0.30 × 0.24 × 0.22 mm
V = 797.95 (7) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3637 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2733 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 16.3280 pixels mm^-1	θ_max = 29.0°, θ_min = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→13
T_min = 0.892, T_max = 1.000	l = −16→16
6470 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0311P)² + 0.0409P] where P = (F_o² + 2F_c²)/3
3637 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₃FNO)]	γ = 69.138 (4)°
M_r = 351.19	V = 797.95 (7) Å³
Triclinic, P1	Z = 2
a = 7.6602 (4) Å	Mo Kα radiation
b = 9.6438 (4) Å	µ = 0.96 mm⁻¹
c = 12.0626 (6) Å	T = 293 K
α = 86.548 (4)°	0.30 × 0.24 × 0.22 mm
β = 73.590 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3637 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2733 reflections with I > 2σ(I)
T_min = 0.892, T_max = 1.000	R_int = 0.039
6470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.32 e Å⁻³
3637 reflections	Δρ_min = −0.42 e Å⁻³
212 parameters

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

	x	y	z	U_iso*/U_eq
Fe	−0.00273 (5)	0.82243 (4)	0.71263 (3)	0.04303 (14)
F1	0.7892 (3)	0.3862 (3)	0.90812 (18)	0.0882 (7)
O1	0.2719 (2)	0.5199 (2)	0.48403 (16)	0.0499 (5)
N1	0.4911 (3)	0.2934 (3)	0.6422 (2)	0.0449 (6)
C1	−0.0198 (3)	0.6710 (3)	0.6119 (2)	0.0372 (6)
C2	−0.1753 (3)	0.7020 (3)	0.7169 (2)	0.0448 (7)
H2	−0.1983	0.6335	0.7714	0.054*
C3	−0.2873 (4)	0.8550 (3)	0.7229 (3)	0.0536 (8)
H3	−0.3970	0.9051	0.7823	0.064*
C4	−0.2040 (4)	0.9184 (3)	0.6233 (3)	0.0560 (8)
H4	−0.2504	1.0178	0.6057	0.067*
C5	−0.0400 (4)	0.8082 (3)	0.5550 (2)	0.0473 (7)
H5	0.0413	0.8216	0.4850	0.057*
C6	0.2666 (5)	0.7445 (4)	0.7374 (4)	0.0795 (12)
H6	0.3657	0.6561	0.7055	0.095*
C7	0.1231 (8)	0.7621 (6)	0.8431 (4)	0.0967 (15)
H7	0.1092	0.6879	0.8941	0.116*
C8	0.0042 (6)	0.9130 (6)	0.8577 (4)	0.0878 (12)
H8	−0.1030	0.9561	0.9206	0.105*
C9	0.0721 (5)	0.9861 (4)	0.7643 (4)	0.0719 (10)
H9	0.0192	1.0871	0.7533	0.086*
C10	0.2342 (4)	0.8836 (4)	0.6881 (3)	0.0671 (9)
H10	0.3074	0.9040	0.6176	0.081*
C11	0.1432 (3)	0.5307 (3)	0.5732 (2)	0.0363 (6)
C12	0.1427 (3)	0.3981 (3)	0.6467 (2)	0.0404 (6)
H12A	0.0391	0.3664	0.6403	0.048*
H12B	0.1158	0.4275	0.7270	0.048*
C13	0.3347 (3)	0.2684 (3)	0.6115 (2)	0.0443 (7)
H13A	0.3168	0.1803	0.6483	0.053*
H13B	0.3718	0.2496	0.5285	0.053*
C14	0.5010 (3)	0.2932 (3)	0.7547 (2)	0.0397 (6)
C15	0.3909 (4)	0.2347 (3)	0.8445 (3)	0.0551 (8)
H15	0.2988	0.2008	0.8311	0.066*
C16	0.4193 (4)	0.2273 (4)	0.9534 (3)	0.0674 (10)
H16	0.3464	0.1870	1.0123	0.081*
C17	0.5519 (4)	0.2778 (4)	0.9769 (3)	0.0672 (9)
H17	0.5706	0.2723	1.0502	0.081*
C18	0.6549 (4)	0.3361 (4)	0.8883 (3)	0.0553 (8)
C19	0.6334 (3)	0.3462 (3)	0.7795 (2)	0.0458 (7)
H19	0.7066	0.3882	0.7222	0.055*
H1N	0.541 (4)	0.349 (3)	0.601 (2)	0.044 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe	0.0435 (2)	0.0423 (2)	0.0477 (3)	−0.01725 (18)	−0.01646 (18)	0.00022 (17)
F1	0.0864 (13)	0.1340 (19)	0.0769 (15)	−0.0679 (14)	−0.0380 (11)	0.0171 (13)
O1	0.0517 (11)	0.0520 (11)	0.0418 (12)	−0.0225 (9)	−0.0014 (9)	0.0042 (9)
N1	0.0368 (12)	0.0494 (14)	0.0487 (16)	−0.0169 (11)	−0.0119 (11)	0.0105 (12)
C1	0.0404 (13)	0.0377 (13)	0.0416 (16)	−0.0184 (11)	−0.0182 (12)	0.0036 (11)
C2	0.0397 (13)	0.0473 (16)	0.0511 (18)	−0.0210 (13)	−0.0116 (12)	0.0060 (13)
C3	0.0384 (14)	0.0529 (18)	0.065 (2)	−0.0101 (14)	−0.0133 (14)	−0.0049 (15)
C4	0.0571 (17)	0.0424 (16)	0.071 (2)	−0.0112 (15)	−0.0320 (16)	0.0091 (15)
C5	0.0583 (16)	0.0459 (15)	0.0442 (17)	−0.0215 (14)	−0.0224 (14)	0.0122 (13)
C6	0.066 (2)	0.065 (2)	0.123 (4)	−0.0124 (19)	−0.061 (2)	−0.011 (2)
C7	0.143 (4)	0.124 (4)	0.089 (3)	−0.090 (3)	−0.087 (3)	0.050 (3)
C8	0.086 (3)	0.131 (4)	0.062 (3)	−0.058 (3)	−0.013 (2)	−0.030 (3)
C9	0.0600 (19)	0.061 (2)	0.100 (3)	−0.0257 (17)	−0.0199 (19)	−0.023 (2)
C10	0.0514 (17)	0.078 (2)	0.081 (3)	−0.0330 (18)	−0.0153 (17)	−0.0121 (19)
C11	0.0393 (13)	0.0392 (14)	0.0380 (15)	−0.0202 (11)	−0.0145 (12)	0.0032 (11)
C12	0.0373 (13)	0.0434 (15)	0.0432 (16)	−0.0184 (12)	−0.0109 (11)	0.0063 (12)
C13	0.0461 (14)	0.0382 (14)	0.0502 (18)	−0.0169 (12)	−0.0136 (13)	0.0034 (12)
C14	0.0323 (12)	0.0375 (14)	0.0425 (16)	−0.0076 (11)	−0.0070 (11)	0.0054 (11)
C15	0.0498 (16)	0.066 (2)	0.059 (2)	−0.0323 (15)	−0.0171 (15)	0.0151 (16)
C16	0.0664 (19)	0.092 (3)	0.050 (2)	−0.0414 (19)	−0.0132 (16)	0.0199 (18)
C17	0.070 (2)	0.096 (3)	0.044 (2)	−0.037 (2)	−0.0199 (16)	0.0094 (18)
C18	0.0460 (15)	0.069 (2)	0.057 (2)	−0.0261 (15)	−0.0169 (14)	0.0030 (16)
C19	0.0372 (13)	0.0527 (17)	0.0475 (18)	−0.0185 (13)	−0.0098 (12)	0.0090 (13)

Geometric parameters (Å, º) top

Fe—C1	2.015 (3)	C6—C7	1.402 (5)
Fe—C5	2.021 (3)	C6—H6	0.9300
Fe—C7	2.023 (3)	C7—C8	1.405 (6)
Fe—C8	2.024 (4)	C7—H7	0.9300
Fe—C6	2.031 (3)	C8—C9	1.368 (5)
Fe—C2	2.036 (3)	C8—H8	0.9300
Fe—C10	2.042 (3)	C9—C10	1.398 (4)
Fe—C9	2.042 (3)	C9—H9	0.9300
Fe—C4	2.048 (3)	C10—H10	0.9300
Fe—C3	2.057 (3)	C11—C12	1.511 (3)
F1—C18	1.362 (3)	C12—C13	1.520 (3)
O1—C11	1.217 (3)	C12—H12A	0.9700
N1—C14	1.380 (4)	C12—H12B	0.9700
N1—C13	1.448 (3)	C13—H13A	0.9700
N1—H1N	0.83 (3)	C13—H13B	0.9700
C1—C5	1.432 (3)	C14—C19	1.392 (4)
C1—C2	1.432 (3)	C14—C15	1.397 (4)
C1—C11	1.467 (3)	C15—C16	1.385 (4)
C2—C3	1.412 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.371 (4)
C3—C4	1.408 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.359 (4)
C4—C5	1.399 (4)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.362 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—C10	1.401 (5)

C1—Fe—C5	41.55 (10)	Fe—C4—H4	127.0
C1—Fe—C7	121.77 (16)	C4—C5—C1	107.9 (2)
C5—Fe—C7	157.2 (2)	C4—C5—Fe	70.97 (17)
C1—Fe—C8	157.73 (16)	C1—C5—Fe	69.04 (15)
C5—Fe—C8	159.81 (17)	C4—C5—H5	126.1
C7—Fe—C8	40.61 (17)	C1—C5—H5	126.1
C1—Fe—C6	107.95 (13)	Fe—C5—H5	125.5
C5—Fe—C6	121.21 (15)	C10—C6—C7	108.0 (3)
C7—Fe—C6	40.47 (16)	C10—C6—Fe	70.29 (17)
C8—Fe—C6	67.65 (16)	C7—C6—Fe	69.46 (19)
C1—Fe—C2	41.40 (10)	C10—C6—H6	126.0
C5—Fe—C2	69.20 (11)	C7—C6—H6	126.0
C7—Fe—C2	108.79 (14)	Fe—C6—H6	125.8
C8—Fe—C2	122.24 (15)	C6—C7—C8	107.1 (3)
C6—Fe—C2	126.19 (13)	C6—C7—Fe	70.07 (19)
C1—Fe—C10	124.64 (12)	C8—C7—Fe	69.7 (2)
C5—Fe—C10	106.96 (13)	C6—C7—H7	126.5
C7—Fe—C10	67.81 (16)	C8—C7—H7	126.5
C8—Fe—C10	67.08 (15)	Fe—C7—H7	125.3
C6—Fe—C10	40.25 (13)	C9—C8—C7	108.8 (4)
C2—Fe—C10	162.67 (12)	C9—C8—Fe	71.0 (2)
C1—Fe—C9	161.18 (13)	C7—C8—Fe	69.6 (2)
C5—Fe—C9	123.84 (14)	C9—C8—H8	125.6
C7—Fe—C9	67.37 (16)	C7—C8—H8	125.6
C8—Fe—C9	39.32 (15)	Fe—C8—H8	125.3
C6—Fe—C9	67.32 (14)	C8—C9—C10	108.6 (4)
C2—Fe—C9	156.06 (13)	C8—C9—Fe	69.6 (2)
C10—Fe—C9	40.02 (13)	C10—C9—Fe	69.97 (19)
C1—Fe—C4	68.51 (11)	C8—C9—H9	125.7
C5—Fe—C4	40.20 (11)	C10—C9—H9	125.7
C7—Fe—C4	161.8 (2)	Fe—C9—H9	126.3
C8—Fe—C4	124.67 (16)	C9—C10—C6	107.5 (3)
C6—Fe—C4	155.86 (16)	C9—C10—Fe	70.01 (18)
C2—Fe—C4	67.94 (11)	C6—C10—Fe	69.46 (19)
C10—Fe—C4	120.74 (14)	C9—C10—H10	126.2
C9—Fe—C4	107.89 (14)	C6—C10—H10	126.2
C1—Fe—C3	68.74 (11)	Fe—C10—H10	125.9
C5—Fe—C3	68.21 (12)	O1—C11—C1	121.5 (2)
C7—Fe—C3	125.88 (17)	O1—C11—C12	121.0 (2)
C8—Fe—C3	108.67 (14)	C1—C11—C12	117.5 (2)
C6—Fe—C3	162.91 (15)	C11—C12—C13	112.7 (2)
C2—Fe—C3	40.37 (10)	C11—C12—H12A	109.1
C10—Fe—C3	155.42 (13)	C13—C12—H12A	109.1
C9—Fe—C3	121.22 (12)	C11—C12—H12B	109.1
C4—Fe—C3	40.10 (11)	C13—C12—H12B	109.1
C14—N1—C13	122.9 (2)	H12A—C12—H12B	107.8
C14—N1—H1N	114 (2)	N1—C13—C12	113.3 (2)
C13—N1—H1N	116.5 (18)	N1—C13—H13A	108.9
C5—C1—C2	107.1 (2)	C12—C13—H13A	108.9
C5—C1—C11	125.0 (2)	N1—C13—H13B	108.9
C2—C1—C11	127.6 (2)	C12—C13—H13B	108.9
C5—C1—Fe	69.42 (16)	H13A—C13—H13B	107.7
C2—C1—Fe	70.07 (15)	N1—C14—C19	119.0 (2)
C11—C1—Fe	121.02 (16)	N1—C14—C15	122.8 (3)
C3—C2—C1	107.8 (2)	C19—C14—C15	118.1 (3)
C3—C2—Fe	70.61 (16)	C16—C15—C14	119.8 (3)
C1—C2—Fe	68.53 (14)	C16—C15—H15	120.1
C3—C2—H2	126.1	C14—C15—H15	120.1
C1—C2—H2	126.1	C17—C16—C15	121.9 (3)
Fe—C2—H2	126.3	C17—C16—H16	119.1
C4—C3—C2	108.0 (2)	C15—C16—H16	119.1
C4—C3—Fe	69.62 (15)	C18—C17—C16	117.0 (3)
C2—C3—Fe	69.02 (14)	C18—C17—H17	121.5
C4—C3—H3	126.0	C16—C17—H17	121.5
C2—C3—H3	126.0	C17—C18—F1	118.7 (3)
Fe—C3—H3	127.0	C17—C18—C19	123.7 (3)
C5—C4—C3	109.1 (2)	F1—C18—C19	117.5 (3)
C5—C4—Fe	68.83 (15)	C18—C19—C14	119.5 (3)
C3—C4—Fe	70.28 (15)	C18—C19—H19	120.3
C5—C4—H4	125.4	C14—C19—H19	120.3
C3—C4—H4	125.4

C7—Fe—C1—C5	−159.4 (2)	C9—Fe—C6—C10	−37.7 (2)
C8—Fe—C1—C5	168.2 (3)	C4—Fe—C6—C10	45.5 (4)
C6—Fe—C1—C5	−117.1 (2)	C3—Fe—C6—C10	−161.3 (4)
C2—Fe—C1—C5	118.1 (2)	C1—Fe—C6—C7	−118.2 (3)
C10—Fe—C1—C5	−75.8 (2)	C5—Fe—C6—C7	−161.9 (2)
C9—Fe—C1—C5	−44.9 (4)	C8—Fe—C6—C7	38.5 (2)
C4—Fe—C1—C5	37.50 (16)	C2—Fe—C6—C7	−76.0 (3)
C3—Fe—C1—C5	80.70 (16)	C10—Fe—C6—C7	118.9 (3)
C5—Fe—C1—C2	−118.1 (2)	C9—Fe—C6—C7	81.2 (3)
C7—Fe—C1—C2	82.6 (2)	C4—Fe—C6—C7	164.4 (3)
C8—Fe—C1—C2	50.1 (4)	C3—Fe—C6—C7	−42.3 (6)
C6—Fe—C1—C2	124.83 (19)	C10—C6—C7—C8	−0.2 (4)
C10—Fe—C1—C2	166.12 (17)	Fe—C6—C7—C8	−60.2 (2)
C9—Fe—C1—C2	−163.0 (3)	C10—C6—C7—Fe	60.0 (2)
C4—Fe—C1—C2	−80.57 (16)	C1—Fe—C7—C6	80.4 (2)
C3—Fe—C1—C2	−37.36 (15)	C5—Fe—C7—C6	43.3 (5)
C5—Fe—C1—C11	119.3 (3)	C8—Fe—C7—C6	−117.8 (3)
C7—Fe—C1—C11	−40.1 (3)	C2—Fe—C7—C6	124.2 (2)
C8—Fe—C1—C11	−72.6 (4)	C10—Fe—C7—C6	−37.6 (2)
C6—Fe—C1—C11	2.1 (3)	C9—Fe—C7—C6	−81.1 (2)
C2—Fe—C1—C11	−122.7 (3)	C4—Fe—C7—C6	−159.4 (4)
C10—Fe—C1—C11	43.4 (3)	C3—Fe—C7—C6	165.9 (2)
C9—Fe—C1—C11	74.3 (4)	C1—Fe—C7—C8	−161.8 (2)
C4—Fe—C1—C11	156.7 (2)	C5—Fe—C7—C8	161.1 (3)
C3—Fe—C1—C11	−160.0 (2)	C6—Fe—C7—C8	117.8 (3)
C5—C1—C2—C3	0.1 (3)	C2—Fe—C7—C8	−118.0 (2)
C11—C1—C2—C3	174.3 (2)	C10—Fe—C7—C8	80.2 (3)
Fe—C1—C2—C3	59.91 (19)	C9—Fe—C7—C8	36.7 (2)
C5—C1—C2—Fe	−59.81 (18)	C4—Fe—C7—C8	−41.6 (6)
C11—C1—C2—Fe	114.4 (3)	C3—Fe—C7—C8	−76.3 (3)
C1—Fe—C2—C3	−119.2 (2)	C6—C7—C8—C9	−0.1 (4)
C5—Fe—C2—C3	−80.42 (18)	Fe—C7—C8—C9	−60.5 (3)
C7—Fe—C2—C3	123.8 (2)	C6—C7—C8—Fe	60.4 (2)
C8—Fe—C2—C3	80.9 (2)	C1—Fe—C8—C9	163.9 (3)
C6—Fe—C2—C3	165.4 (2)	C5—Fe—C8—C9	−39.3 (5)
C10—Fe—C2—C3	−160.7 (4)	C7—Fe—C8—C9	119.4 (3)
C9—Fe—C2—C3	47.4 (4)	C6—Fe—C8—C9	81.0 (2)
C4—Fe—C2—C3	−37.11 (17)	C2—Fe—C8—C9	−159.27 (18)
C5—Fe—C2—C1	38.76 (14)	C10—Fe—C8—C9	37.3 (2)
C7—Fe—C2—C1	−117.1 (2)	C4—Fe—C8—C9	−75.2 (3)
C8—Fe—C2—C1	−159.89 (19)	C3—Fe—C8—C9	−116.8 (2)
C6—Fe—C2—C1	−75.4 (2)	C1—Fe—C8—C7	44.5 (5)
C10—Fe—C2—C1	−41.5 (5)	C5—Fe—C8—C7	−158.7 (4)
C9—Fe—C2—C1	166.5 (3)	C6—Fe—C8—C7	−38.4 (2)
C4—Fe—C2—C1	82.07 (16)	C2—Fe—C8—C7	81.3 (3)
C3—Fe—C2—C1	119.2 (2)	C10—Fe—C8—C7	−82.1 (3)
C1—C2—C3—C4	0.2 (3)	C9—Fe—C8—C7	−119.4 (3)
Fe—C2—C3—C4	58.9 (2)	C4—Fe—C8—C7	165.4 (2)
C1—C2—C3—Fe	−58.60 (18)	C3—Fe—C8—C7	123.8 (3)
C1—Fe—C3—C4	−81.48 (19)	C7—C8—C9—C10	0.4 (4)
C5—Fe—C3—C4	−36.66 (18)	Fe—C8—C9—C10	−59.3 (2)
C7—Fe—C3—C4	164.0 (2)	C7—C8—C9—Fe	59.6 (3)
C8—Fe—C3—C4	122.1 (2)	C1—Fe—C9—C8	−160.9 (3)
C6—Fe—C3—C4	−163.4 (5)	C5—Fe—C9—C8	164.7 (2)
C2—Fe—C3—C4	−119.8 (3)	C7—Fe—C9—C8	−37.9 (2)
C10—Fe—C3—C4	46.5 (4)	C6—Fe—C9—C8	−81.9 (3)
C9—Fe—C3—C4	80.7 (2)	C2—Fe—C9—C8	47.5 (4)
C1—Fe—C3—C2	38.28 (16)	C10—Fe—C9—C8	−119.9 (3)
C5—Fe—C3—C2	83.11 (18)	C4—Fe—C9—C8	123.3 (2)
C7—Fe—C3—C2	−76.3 (3)	C3—Fe—C9—C8	81.4 (3)
C8—Fe—C3—C2	−118.2 (2)	C1—Fe—C9—C10	−41.1 (5)
C6—Fe—C3—C2	−43.6 (5)	C5—Fe—C9—C10	−75.4 (3)
C10—Fe—C3—C2	166.3 (3)	C7—Fe—C9—C10	82.0 (3)
C9—Fe—C3—C2	−159.6 (2)	C8—Fe—C9—C10	119.9 (3)
C4—Fe—C3—C2	119.8 (3)	C6—Fe—C9—C10	37.9 (2)
C2—C3—C4—C5	−0.5 (3)	C2—Fe—C9—C10	167.4 (3)
Fe—C3—C4—C5	58.0 (2)	C4—Fe—C9—C10	−116.8 (2)
C2—C3—C4—Fe	−58.5 (2)	C3—Fe—C9—C10	−158.7 (2)
C1—Fe—C4—C5	−38.72 (16)	C8—C9—C10—C6	−0.5 (4)
C7—Fe—C4—C5	−166.6 (4)	Fe—C9—C10—C6	−59.6 (2)
C8—Fe—C4—C5	161.7 (2)	C8—C9—C10—Fe	59.1 (2)
C6—Fe—C4—C5	47.3 (4)	C7—C6—C10—C9	0.4 (4)
C2—Fe—C4—C5	−83.46 (18)	Fe—C6—C10—C9	59.9 (2)
C10—Fe—C4—C5	79.8 (2)	C7—C6—C10—Fe	−59.5 (2)
C9—Fe—C4—C5	121.65 (19)	C1—Fe—C10—C9	165.1 (2)
C3—Fe—C4—C5	−120.8 (3)	C5—Fe—C10—C9	122.8 (2)
C1—Fe—C4—C3	82.09 (18)	C7—Fe—C10—C9	−80.8 (3)
C5—Fe—C4—C3	120.8 (3)	C8—Fe—C10—C9	−36.6 (2)
C7—Fe—C4—C3	−45.8 (5)	C6—Fe—C10—C9	−118.6 (3)
C8—Fe—C4—C3	−77.5 (2)	C2—Fe—C10—C9	−162.7 (4)
C6—Fe—C4—C3	168.2 (3)	C4—Fe—C10—C9	81.2 (3)
C2—Fe—C4—C3	37.35 (18)	C3—Fe—C10—C9	48.3 (4)
C10—Fe—C4—C3	−159.44 (18)	C1—Fe—C10—C6	−76.3 (3)
C9—Fe—C4—C3	−117.5 (2)	C5—Fe—C10—C6	−118.6 (2)
C3—C4—C5—C1	0.6 (3)	C7—Fe—C10—C6	37.8 (2)
Fe—C4—C5—C1	59.42 (18)	C8—Fe—C10—C6	82.0 (3)
C3—C4—C5—Fe	−58.8 (2)	C2—Fe—C10—C6	−44.1 (5)
C2—C1—C5—C4	−0.4 (3)	C9—Fe—C10—C6	118.6 (3)
C11—C1—C5—C4	−174.8 (2)	C4—Fe—C10—C6	−160.2 (2)
Fe—C1—C5—C4	−60.6 (2)	C3—Fe—C10—C6	166.9 (3)
C2—C1—C5—Fe	60.22 (18)	C5—C1—C11—O1	−3.5 (4)
C11—C1—C5—Fe	−114.1 (2)	C2—C1—C11—O1	−176.7 (3)
C1—Fe—C5—C4	118.7 (2)	Fe—C1—C11—O1	−88.9 (3)
C7—Fe—C5—C4	169.2 (3)	C5—C1—C11—C12	178.2 (2)
C8—Fe—C5—C4	−48.4 (4)	C2—C1—C11—C12	5.0 (4)
C6—Fe—C5—C4	−159.41 (19)	Fe—C1—C11—C12	92.8 (2)
C2—Fe—C5—C4	80.03 (18)	O1—C11—C12—C13	12.5 (4)
C10—Fe—C5—C4	−117.84 (19)	C1—C11—C12—C13	−169.1 (2)
C9—Fe—C5—C4	−77.3 (2)	C14—N1—C13—C12	72.1 (3)
C3—Fe—C5—C4	36.57 (17)	C11—C12—C13—N1	71.8 (3)
C7—Fe—C5—C1	50.6 (4)	C13—N1—C14—C19	−167.6 (2)
C8—Fe—C5—C1	−167.0 (3)	C13—N1—C14—C15	15.9 (4)
C6—Fe—C5—C1	81.9 (2)	N1—C14—C15—C16	174.8 (3)
C2—Fe—C5—C1	−38.62 (14)	C19—C14—C15—C16	−1.7 (4)
C10—Fe—C5—C1	123.50 (17)	C14—C15—C16—C17	0.8 (5)
C9—Fe—C5—C1	164.08 (15)	C15—C16—C17—C18	0.2 (5)
C4—Fe—C5—C1	−118.7 (2)	C16—C17—C18—F1	−179.4 (3)
C3—Fe—C5—C1	−82.09 (16)	C16—C17—C18—C19	−0.2 (5)
C1—Fe—C6—C10	122.8 (2)	C17—C18—C19—C14	−0.7 (5)
C5—Fe—C6—C10	79.2 (2)	F1—C18—C19—C14	178.5 (3)
C7—Fe—C6—C10	−118.9 (3)	N1—C14—C19—C18	−175.0 (2)
C8—Fe—C6—C10	−80.4 (3)	C15—C14—C19—C18	1.6 (4)
C2—Fe—C6—C10	165.10 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (3)	2.24 (3)	3.049 (3)	165 (3)
C19—H19···O1ⁱ	0.93	2.57	3.342 (3)	141
C4—H4···N1ⁱⁱ	0.93	2.66	3.517 (3)	153

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₄H₁₃FNO)]
M_r	351.19
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.6602 (4), 9.6438 (4), 12.0626 (6)
α, β, γ (°)	86.548 (4), 73.590 (4), 69.138 (4)
V (Å³)	797.95 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.30 × 0.24 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.892, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6470, 3637, 2733
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.102, 1.06
No. of reflections	3637
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.42

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and POV-RAY (Persistence of Vision, 2004), WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (3)	2.24 (3)	3.049 (3)	165 (3)
C19—H19···O1ⁱ	0.93	2.57	3.342 (3)	141
C4—H4···N1ⁱⁱ	0.93	2.66	3.517 (3)	153

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y+1, z.

Acknowledgements

This work was supported by the Ministry of Education and Science of the Republic of Serbia (project Nos. 172014, 172035 and 172034). We thank Dr Vladimir Divjaković for help with the X-ray data collection.

References

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