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Acta Cryst. (2012). E68, m231    [ doi:10.1107/S1600536812003510 ]

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

Z. Leka, S. B. Novakovic, A. Pejovic, G. A. Bogdanovic and R. D. Vukicevic

Abstract top

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.

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).

Refinement top

H atoms bonded to C atoms were placed at geometrically calculated positions and refined using a riding model. C—H distances were fixed to 0.93 and 0.97 Å from aromatic and methylene C atoms respectively. The Uiso(H) values were equal to 1.2 times Ueq of the corresponding parent atom. H atom attached to N atom was isotropically refined.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 40% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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
Mr = 351.19F(000) = 364
Triclinic, P1Dx = 1.462 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6602 (4) ÅCell parameters from 2586 reflections
b = 9.6438 (4) Åθ = 3.0–29.0°
c = 12.0626 (6) ŵ = 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 Source2733 reflections with I > 2σ(I)
graphiteRint = 0.039
Detector resolution: 16.3280 pixels mm-1θmax = 29.0°, θmin = 3.0°
ω scansh = −10→10
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		k = −12→13
Tmin = 0.892, Tmax = 1.000l = −16→16
6470 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0311P)2 + 0.0409P]
where P = (Fo2 + 2Fc2)/3
3637 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
[Fe(C5H5)(C14H13FNO)]γ = 69.138 (4)°
Mr = 351.19V = 797.95 (7) Å3
Triclinic, P1Z = 2
a = 7.6602 (4) ÅMo Kα radiation
b = 9.6438 (4) ŵ = 0.96 mm−1
c = 12.0626 (6) ÅT = 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)
Tmin = 0.892, Tmax = 1.000Rint = 0.039
6470 measured reflectionsθmax = 29.0°
Refinement top
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102Δρmax = 0.32 e Å−3
S = 1.06Δρmin = −0.42 e Å−3
3637 reflectionsAbsolute structure: ?
212 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe−0.00273 (5)0.82243 (4)0.71263 (3)0.04303 (14)
F10.7892 (3)0.3862 (3)0.90812 (18)0.0882 (7)
O10.2719 (2)0.5199 (2)0.48403 (16)0.0499 (5)
N10.4911 (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)
H2−0.19830.63350.77140.054*
C3−0.2873 (4)0.8550 (3)0.7229 (3)0.0536 (8)
H3−0.39700.90510.78230.064*
C4−0.2040 (4)0.9184 (3)0.6233 (3)0.0560 (8)
H4−0.25041.01780.60570.067*
C5−0.0400 (4)0.8082 (3)0.5550 (2)0.0473 (7)
H50.04130.82160.48500.057*
C60.2666 (5)0.7445 (4)0.7374 (4)0.0795 (12)
H60.36570.65610.70550.095*
C70.1231 (8)0.7621 (6)0.8431 (4)0.0967 (15)
H70.10920.68790.89410.116*
C80.0042 (6)0.9130 (6)0.8577 (4)0.0878 (12)
H8−0.10300.95610.92060.105*
C90.0721 (5)0.9861 (4)0.7643 (4)0.0719 (10)
H90.01921.08710.75330.086*
C100.2342 (4)0.8836 (4)0.6881 (3)0.0671 (9)
H100.30740.90400.61760.081*
C110.1432 (3)0.5307 (3)0.5732 (2)0.0363 (6)
C120.1427 (3)0.3981 (3)0.6467 (2)0.0404 (6)
H12A0.03910.36640.64030.048*
H12B0.11580.42750.72700.048*
C130.3347 (3)0.2684 (3)0.6115 (2)0.0443 (7)
H13A0.31680.18030.64830.053*
H13B0.37180.24960.52850.053*
C140.5010 (3)0.2932 (3)0.7547 (2)0.0397 (6)
C150.3909 (4)0.2347 (3)0.8445 (3)0.0551 (8)
H150.29880.20080.83110.066*
C160.4193 (4)0.2273 (4)0.9534 (3)0.0674 (10)
H160.34640.18701.01230.081*
C170.5519 (4)0.2778 (4)0.9769 (3)0.0672 (9)
H170.57060.27231.05020.081*
C180.6549 (4)0.3361 (4)0.8883 (3)0.0553 (8)
C190.6334 (3)0.3462 (3)0.7795 (2)0.0458 (7)
H190.70660.38820.72220.055*
H1N0.541 (4)0.349 (3)0.601 (2)0.044 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe0.0435 (2)0.0423 (2)0.0477 (3)−0.01725 (18)−0.01646 (18)0.00022 (17)
F10.0864 (13)0.1340 (19)0.0769 (15)−0.0679 (14)−0.0380 (11)0.0171 (13)
O10.0517 (11)0.0520 (11)0.0418 (12)−0.0225 (9)−0.0014 (9)0.0042 (9)
N10.0368 (12)0.0494 (14)0.0487 (16)−0.0169 (11)−0.0119 (11)0.0105 (12)
C10.0404 (13)0.0377 (13)0.0416 (16)−0.0184 (11)−0.0182 (12)0.0036 (11)
C20.0397 (13)0.0473 (16)0.0511 (18)−0.0210 (13)−0.0116 (12)0.0060 (13)
C30.0384 (14)0.0529 (18)0.065 (2)−0.0101 (14)−0.0133 (14)−0.0049 (15)
C40.0571 (17)0.0424 (16)0.071 (2)−0.0112 (15)−0.0320 (16)0.0091 (15)
C50.0583 (16)0.0459 (15)0.0442 (17)−0.0215 (14)−0.0224 (14)0.0122 (13)
C60.066 (2)0.065 (2)0.123 (4)−0.0124 (19)−0.061 (2)−0.011 (2)
C70.143 (4)0.124 (4)0.089 (3)−0.090 (3)−0.087 (3)0.050 (3)
C80.086 (3)0.131 (4)0.062 (3)−0.058 (3)−0.013 (2)−0.030 (3)
C90.0600 (19)0.061 (2)0.100 (3)−0.0257 (17)−0.0199 (19)−0.023 (2)
C100.0514 (17)0.078 (2)0.081 (3)−0.0330 (18)−0.0153 (17)−0.0121 (19)
C110.0393 (13)0.0392 (14)0.0380 (15)−0.0202 (11)−0.0145 (12)0.0032 (11)
C120.0373 (13)0.0434 (15)0.0432 (16)−0.0184 (12)−0.0109 (11)0.0063 (12)
C130.0461 (14)0.0382 (14)0.0502 (18)−0.0169 (12)−0.0136 (13)0.0034 (12)
C140.0323 (12)0.0375 (14)0.0425 (16)−0.0076 (11)−0.0070 (11)0.0054 (11)
C150.0498 (16)0.066 (2)0.059 (2)−0.0323 (15)−0.0171 (15)0.0151 (16)
C160.0664 (19)0.092 (3)0.050 (2)−0.0414 (19)−0.0132 (16)0.0199 (18)
C170.070 (2)0.096 (3)0.044 (2)−0.037 (2)−0.0199 (16)0.0094 (18)
C180.0460 (15)0.069 (2)0.057 (2)−0.0261 (15)−0.0169 (14)0.0030 (16)
C190.0372 (13)0.0527 (17)0.0475 (18)−0.0185 (13)−0.0098 (12)0.0090 (13)
Geometric parameters (Å, °) top
Fe—C12.015 (3)C6—C71.402 (5)
Fe—C52.021 (3)C6—H60.9300
Fe—C72.023 (3)C7—C81.405 (6)
Fe—C82.024 (4)C7—H70.9300
Fe—C62.031 (3)C8—C91.368 (5)
Fe—C22.036 (3)C8—H80.9300
Fe—C102.042 (3)C9—C101.398 (4)
Fe—C92.042 (3)C9—H90.9300
Fe—C42.048 (3)C10—H100.9300
Fe—C32.057 (3)C11—C121.511 (3)
F1—C181.362 (3)C12—C131.520 (3)
O1—C111.217 (3)C12—H12A0.9700
N1—C141.380 (4)C12—H12B0.9700
N1—C131.448 (3)C13—H13A0.9700
N1—H1N0.83 (3)C13—H13B0.9700
C1—C51.432 (3)C14—C191.392 (4)
C1—C21.432 (3)C14—C151.397 (4)
C1—C111.467 (3)C15—C161.385 (4)
C2—C31.412 (4)C15—H150.9300
C2—H20.9300C16—C171.371 (4)
C3—C41.408 (4)C16—H160.9300
C3—H30.9300C17—C181.359 (4)
C4—C51.399 (4)C17—H170.9300
C4—H40.9300C18—C191.362 (4)
C5—H50.9300C19—H190.9300
C6—C101.401 (5)
C1—Fe—C541.55 (10)Fe—C4—H4127.0
C1—Fe—C7121.77 (16)C4—C5—C1107.9 (2)
C5—Fe—C7157.2 (2)C4—C5—Fe70.97 (17)
C1—Fe—C8157.73 (16)C1—C5—Fe69.04 (15)
C5—Fe—C8159.81 (17)C4—C5—H5126.1
C7—Fe—C840.61 (17)C1—C5—H5126.1
C1—Fe—C6107.95 (13)Fe—C5—H5125.5
C5—Fe—C6121.21 (15)C10—C6—C7108.0 (3)
C7—Fe—C640.47 (16)C10—C6—Fe70.29 (17)
C8—Fe—C667.65 (16)C7—C6—Fe69.46 (19)
C1—Fe—C241.40 (10)C10—C6—H6126.0
C5—Fe—C269.20 (11)C7—C6—H6126.0
C7—Fe—C2108.79 (14)Fe—C6—H6125.8
C8—Fe—C2122.24 (15)C6—C7—C8107.1 (3)
C6—Fe—C2126.19 (13)C6—C7—Fe70.07 (19)
C1—Fe—C10124.64 (12)C8—C7—Fe69.7 (2)
C5—Fe—C10106.96 (13)C6—C7—H7126.5
C7—Fe—C1067.81 (16)C8—C7—H7126.5
C8—Fe—C1067.08 (15)Fe—C7—H7125.3
C6—Fe—C1040.25 (13)C9—C8—C7108.8 (4)
C2—Fe—C10162.67 (12)C9—C8—Fe71.0 (2)
C1—Fe—C9161.18 (13)C7—C8—Fe69.6 (2)
C5—Fe—C9123.84 (14)C9—C8—H8125.6
C7—Fe—C967.37 (16)C7—C8—H8125.6
C8—Fe—C939.32 (15)Fe—C8—H8125.3
C6—Fe—C967.32 (14)C8—C9—C10108.6 (4)
C2—Fe—C9156.06 (13)C8—C9—Fe69.6 (2)
C10—Fe—C940.02 (13)C10—C9—Fe69.97 (19)
C1—Fe—C468.51 (11)C8—C9—H9125.7
C5—Fe—C440.20 (11)C10—C9—H9125.7
C7—Fe—C4161.8 (2)Fe—C9—H9126.3
C8—Fe—C4124.67 (16)C9—C10—C6107.5 (3)
C6—Fe—C4155.86 (16)C9—C10—Fe70.01 (18)
C2—Fe—C467.94 (11)C6—C10—Fe69.46 (19)
C10—Fe—C4120.74 (14)C9—C10—H10126.2
C9—Fe—C4107.89 (14)C6—C10—H10126.2
C1—Fe—C368.74 (11)Fe—C10—H10125.9
C5—Fe—C368.21 (12)O1—C11—C1121.5 (2)
C7—Fe—C3125.88 (17)O1—C11—C12121.0 (2)
C8—Fe—C3108.67 (14)C1—C11—C12117.5 (2)
C6—Fe—C3162.91 (15)C11—C12—C13112.7 (2)
C2—Fe—C340.37 (10)C11—C12—H12A109.1
C10—Fe—C3155.42 (13)C13—C12—H12A109.1
C9—Fe—C3121.22 (12)C11—C12—H12B109.1
C4—Fe—C340.10 (11)C13—C12—H12B109.1
C14—N1—C13122.9 (2)H12A—C12—H12B107.8
C14—N1—H1N114 (2)N1—C13—C12113.3 (2)
C13—N1—H1N116.5 (18)N1—C13—H13A108.9
C5—C1—C2107.1 (2)C12—C13—H13A108.9
C5—C1—C11125.0 (2)N1—C13—H13B108.9
C2—C1—C11127.6 (2)C12—C13—H13B108.9
C5—C1—Fe69.42 (16)H13A—C13—H13B107.7
C2—C1—Fe70.07 (15)N1—C14—C19119.0 (2)
C11—C1—Fe121.02 (16)N1—C14—C15122.8 (3)
C3—C2—C1107.8 (2)C19—C14—C15118.1 (3)
C3—C2—Fe70.61 (16)C16—C15—C14119.8 (3)
C1—C2—Fe68.53 (14)C16—C15—H15120.1
C3—C2—H2126.1C14—C15—H15120.1
C1—C2—H2126.1C17—C16—C15121.9 (3)
Fe—C2—H2126.3C17—C16—H16119.1
C4—C3—C2108.0 (2)C15—C16—H16119.1
C4—C3—Fe69.62 (15)C18—C17—C16117.0 (3)
C2—C3—Fe69.02 (14)C18—C17—H17121.5
C4—C3—H3126.0C16—C17—H17121.5
C2—C3—H3126.0C17—C18—F1118.7 (3)
Fe—C3—H3127.0C17—C18—C19123.7 (3)
C5—C4—C3109.1 (2)F1—C18—C19117.5 (3)
C5—C4—Fe68.83 (15)C18—C19—C14119.5 (3)
C3—C4—Fe70.28 (15)C18—C19—H19120.3
C5—C4—H4125.4C14—C19—H19120.3
C3—C4—H4125.4
C7—Fe—C1—C5−159.4 (2)C9—Fe—C6—C10−37.7 (2)
C8—Fe—C1—C5168.2 (3)C4—Fe—C6—C1045.5 (4)
C6—Fe—C1—C5−117.1 (2)C3—Fe—C6—C10−161.3 (4)
C2—Fe—C1—C5118.1 (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—C738.5 (2)
C4—Fe—C1—C537.50 (16)C2—Fe—C6—C7−76.0 (3)
C3—Fe—C1—C580.70 (16)C10—Fe—C6—C7118.9 (3)
C5—Fe—C1—C2−118.1 (2)C9—Fe—C6—C781.2 (3)
C7—Fe—C1—C282.6 (2)C4—Fe—C6—C7164.4 (3)
C8—Fe—C1—C250.1 (4)C3—Fe—C6—C7−42.3 (6)
C6—Fe—C1—C2124.83 (19)C10—C6—C7—C8−0.2 (4)
C10—Fe—C1—C2166.12 (17)Fe—C6—C7—C8−60.2 (2)
C9—Fe—C1—C2−163.0 (3)C10—C6—C7—Fe60.0 (2)
C4—Fe—C1—C2−80.57 (16)C1—Fe—C7—C680.4 (2)
C3—Fe—C1—C2−37.36 (15)C5—Fe—C7—C643.3 (5)
C5—Fe—C1—C11119.3 (3)C8—Fe—C7—C6−117.8 (3)
C7—Fe—C1—C11−40.1 (3)C2—Fe—C7—C6124.2 (2)
C8—Fe—C1—C11−72.6 (4)C10—Fe—C7—C6−37.6 (2)
C6—Fe—C1—C112.1 (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—C1143.4 (3)C3—Fe—C7—C6165.9 (2)
C9—Fe—C1—C1174.3 (4)C1—Fe—C7—C8−161.8 (2)
C4—Fe—C1—C11156.7 (2)C5—Fe—C7—C8161.1 (3)
C3—Fe—C1—C11−160.0 (2)C6—Fe—C7—C8117.8 (3)
C5—C1—C2—C30.1 (3)C2—Fe—C7—C8−118.0 (2)
C11—C1—C2—C3174.3 (2)C10—Fe—C7—C880.2 (3)
Fe—C1—C2—C359.91 (19)C9—Fe—C7—C836.7 (2)
C5—C1—C2—Fe−59.81 (18)C4—Fe—C7—C8−41.6 (6)
C11—C1—C2—Fe114.4 (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—C3123.8 (2)C6—C7—C8—Fe60.4 (2)
C8—Fe—C2—C380.9 (2)C1—Fe—C8—C9163.9 (3)
C6—Fe—C2—C3165.4 (2)C5—Fe—C8—C9−39.3 (5)
C10—Fe—C2—C3−160.7 (4)C7—Fe—C8—C9119.4 (3)
C9—Fe—C2—C347.4 (4)C6—Fe—C8—C981.0 (2)
C4—Fe—C2—C3−37.11 (17)C2—Fe—C8—C9−159.27 (18)
C5—Fe—C2—C138.76 (14)C10—Fe—C8—C937.3 (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—C744.5 (5)
C10—Fe—C2—C1−41.5 (5)C5—Fe—C8—C7−158.7 (4)
C9—Fe—C2—C1166.5 (3)C6—Fe—C8—C7−38.4 (2)
C4—Fe—C2—C182.07 (16)C2—Fe—C8—C781.3 (3)
C3—Fe—C2—C1119.2 (2)C10—Fe—C8—C7−82.1 (3)
C1—C2—C3—C40.2 (3)C9—Fe—C8—C7−119.4 (3)
Fe—C2—C3—C458.9 (2)C4—Fe—C8—C7165.4 (2)
C1—C2—C3—Fe−58.60 (18)C3—Fe—C8—C7123.8 (3)
C1—Fe—C3—C4−81.48 (19)C7—C8—C9—C100.4 (4)
C5—Fe—C3—C4−36.66 (18)Fe—C8—C9—C10−59.3 (2)
C7—Fe—C3—C4164.0 (2)C7—C8—C9—Fe59.6 (3)
C8—Fe—C3—C4122.1 (2)C1—Fe—C9—C8−160.9 (3)
C6—Fe—C3—C4−163.4 (5)C5—Fe—C9—C8164.7 (2)
C2—Fe—C3—C4−119.8 (3)C7—Fe—C9—C8−37.9 (2)
C10—Fe—C3—C446.5 (4)C6—Fe—C9—C8−81.9 (3)
C9—Fe—C3—C480.7 (2)C2—Fe—C9—C847.5 (4)
C1—Fe—C3—C238.28 (16)C10—Fe—C9—C8−119.9 (3)
C5—Fe—C3—C283.11 (18)C4—Fe—C9—C8123.3 (2)
C7—Fe—C3—C2−76.3 (3)C3—Fe—C9—C881.4 (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—C2166.3 (3)C7—Fe—C9—C1082.0 (3)
C9—Fe—C3—C2−159.6 (2)C8—Fe—C9—C10119.9 (3)
C4—Fe—C3—C2119.8 (3)C6—Fe—C9—C1037.9 (2)
C2—C3—C4—C5−0.5 (3)C2—Fe—C9—C10167.4 (3)
Fe—C3—C4—C558.0 (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—C5161.7 (2)C8—C9—C10—Fe59.1 (2)
C6—Fe—C4—C547.3 (4)C7—C6—C10—C90.4 (4)
C2—Fe—C4—C5−83.46 (18)Fe—C6—C10—C959.9 (2)
C10—Fe—C4—C579.8 (2)C7—C6—C10—Fe−59.5 (2)
C9—Fe—C4—C5121.65 (19)C1—Fe—C10—C9165.1 (2)
C3—Fe—C4—C5−120.8 (3)C5—Fe—C10—C9122.8 (2)
C1—Fe—C4—C382.09 (18)C7—Fe—C10—C9−80.8 (3)
C5—Fe—C4—C3120.8 (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—C3168.2 (3)C4—Fe—C10—C981.2 (3)
C2—Fe—C4—C337.35 (18)C3—Fe—C10—C948.3 (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—C10.6 (3)C7—Fe—C10—C637.8 (2)
Fe—C4—C5—C159.42 (18)C8—Fe—C10—C682.0 (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—C6118.6 (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—C6166.9 (3)
C2—C1—C5—Fe60.22 (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—C4118.7 (2)Fe—C1—C11—O1−88.9 (3)
C7—Fe—C5—C4169.2 (3)C5—C1—C11—C12178.2 (2)
C8—Fe—C5—C4−48.4 (4)C2—C1—C11—C125.0 (4)
C6—Fe—C5—C4−159.41 (19)Fe—C1—C11—C1292.8 (2)
C2—Fe—C5—C480.03 (18)O1—C11—C12—C1312.5 (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—C1272.1 (3)
C3—Fe—C5—C436.57 (17)C11—C12—C13—N171.8 (3)
C7—Fe—C5—C150.6 (4)C13—N1—C14—C19−167.6 (2)
C8—Fe—C5—C1−167.0 (3)C13—N1—C14—C1515.9 (4)
C6—Fe—C5—C181.9 (2)N1—C14—C15—C16174.8 (3)
C2—Fe—C5—C1−38.62 (14)C19—C14—C15—C16−1.7 (4)
C10—Fe—C5—C1123.50 (17)C14—C15—C16—C170.8 (5)
C9—Fe—C5—C1164.08 (15)C15—C16—C17—C180.2 (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—C10122.8 (2)C17—C18—C19—C14−0.7 (5)
C5—Fe—C6—C1079.2 (2)F1—C18—C19—C14178.5 (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—C181.6 (4)
C2—Fe—C6—C10165.10 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.83 (3)2.24 (3)3.049 (3)165 (3)
C19—H19···O1i0.932.573.342 (3)141
C4—H4···N1ii0.932.663.517 (3)153
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.83 (3)2.24 (3)3.049 (3)165 (3)
C19—H19···O1i0.932.573.342 (3)141
C4—H4···N1ii0.932.663.517 (3)153
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y+1, z.
Acknowledgements top

This work was supported by the Ministry of Education and Science of the Republic of Serbia (project Nos. 172014, 172035 and 172034).

references
References top

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