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Acta Crystallogr Sect E Struct Rep Online. 2012 October 1; 68(Pt 10): m1318.
Published online 2012 September 29. doi:  10.1107/S1600536812039177
PMCID: PMC3470183

N-Ferrocenylmethyl-2-nitro­aniline

Abstract

In the title compound, [Fe(C5H5)(C12H11N2O2)], the two cyclo­penta­dienyl (Cp) rings are nearly eclipsed and parallel to each other, the dihedral angle between their mean planes being 2.54 (1)°. One of the Cp rings is substituted by a nitro­benzenamine group, which is essentially perpendicular to the substituted cyclo­penta­dienyl ring, with an N—C(H2)—C—C torsion angle of 89.8 (2)°. Intra­molecular N—H(...)O and N—H(...)N hydrogen bonds occur. In the crystal, weak C—H(...)O hydrogen bonds link adjacent mol­ecules.

Related literature  

For background to the design and properties of ferrocene derivatives, see: Argyropoulos & Coutouli-Argyropoulou (2002 [triangle]); Cano et al. (1995 [triangle]); Shaabani & Shaghaghi (2010 [triangle]). For the synthesis of (ferrocenylmeth­yl)trimethyl­ammonium iodide, see: Osgerby & Pauson (1961 [triangle]). For a related structure, see: Khelef et al. (2012 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-m1318-scheme1.jpg

Experimental  

Crystal data  

  • [Fe(C5H5)(C12H11N2O2)]
  • M r = 336.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-m1318-efi1.jpg
  • a = 10.3609 (3) Å
  • b = 7.8700 (2) Å
  • c = 17.7948 (7) Å
  • β = 93.043 (2)°
  • V = 1448.95 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.05 mm−1
  • T = 293 K
  • 0.3 × 0.1 × 0.1 mm

Data collection  

  • Nonius KappaCCD diffractometer
  • 14651 measured reflections
  • 3204 independent reflections
  • 2881 reflections with I > 2σ(I)
  • R int = 0.028

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.069
  • S = 1.05
  • 3204 reflections
  • 203 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039177/zq2180sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039177/zq2180Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This research was financed by the Laboratory of Valorization and Promotion of Saharan Resources (project No. E03220080002). The authors acknowledge the assistance of Merazig Hocine in the data collection.

supplementary crystallographic information

Comment

Ferrocene derivatives have attracted the attention of many groups of researchers because of their utility in organic synthesis (Cano et al., 1995), medicinal chemistry (Argyropoulos & Coutouli-Argyropoulou, 2002) and in electrochemical studies (Shaabani & Shaghaghi, 2010). Herein, as a continuation of our research related to ferrocene derivatives (Khelef et al., 2012), we report the synthesis and X-ray diffraction characterization of the title compound.

In the title compound, [Fe(C5H5)(C12H11N2O2)], the two cyclopentadienyl (Cp) rings are nearly eclipsed and parallel to each other, the dihedral angle between the mean planes is 2.54 (1)°. One of the Cp ring is substituted by a nitrobenzenamine group which is essentially perpendicular to the substituted cyclopentadienyl ring, with a N—C(H2)—C—C torsion angle of -79.83 (2)°. Weak C—H···O hydrogen bonds link adjacent molecules (Table 1).

Experimental

(Ferrocenylmethyl)trimethylammonium iodide was synthesized according to the reported methods of Osgerby & Pauson (Osgerby & Pauson, 1961). N-(Ferrocenylmethyl)-2-nitrobenzenamine was synthesized as follows: 2-nitroaniline (2.14 g, 15.48 mmol) was added in small portions to a well stirred solution of (ferrocenylmethyl)trimethylammonium iodide (6 g, 15.48 mmol) in water (120 cm3). The resulting mixture was then heated at 110–115°C for 6 h. It was then allowed to cool to room temperature. The obtained precipitate was separated by filtration, washed with water to remove any trace of unchanged (ferrocenylmethy)trimethylammonium iodide and finally recrystallized from ethanol 95% to produce the title compound as cinnabar-red needles (4.85 g, 92%; m.p. 110–112°C).

1H NMR (CDCl3): 4.14 (d, 2H, J = 4.73 Hz, CH2Fc); 4.21 (t, 2H, J = 1.88 Hz, η5-C5H4ortho); 4.27 (s, 5H, η5-C5H5); 4.28 (d, 2H, η5-C5H4meta); 6.68 (t, 1H, J = 7.18 Hz, ArH); 6.90 (d, 1H, J = 8.49 Hz, ArH); 7.47 (t, 1H, J = 8.12 Hz, ArH); 8.23 (dd, 1H, J = 8.12 Hz, ArH); 8.37 (s, 1H, NH).

13C NMR (CDCl3): 42.3 (-ve DEPT) (1 C, CH2Fc); 67.3 (2 C, η5-C5H4meta); 68.1 (2 C, η5-C5H4); 68.8 (5 C, η5-C5H5); 84.5 (1 C, η5-C5H4); 113.8 (1 C, C6H4); 115.3 (1 C, C6H4);126.9 (1 C, C6H4); 131.8 (1 C, C6H4); 136.3 (1 C, C6H4); 144.9 (1 C, C6H4).

Refinement

All hydrogen positions, except H10, were calculated after each cycle of refinement using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene H atoms. The N-bound hydrogen atom, H10, was located in a difference Fourier map and freely refined.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atomic numbering scheme and 50% probability displacement ellipsoids.

Crystal data

[Fe(C5H5)(C12H11N2O2)]Z = 4
Mr = 336.17F(000) = 696
Monoclinic, P21/aDx = 1.541 Mg m3
Hall symbol: -P 2yabMo Kα radiation, λ = 0.71073 Å
a = 10.3609 (3) Åθ = 1.2–27.4°
b = 7.8700 (2) ŵ = 1.05 mm1
c = 17.7948 (7) ÅT = 293 K
β = 93.043 (2)°Needle, red
V = 1448.95 (8) Å30.3 × 0.1 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer2881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 27.4°, θmin = 1.2°
Detector resolution: 9 pixels mm-1h = −13→13
CCD scansk = −10→10
14651 measured reflectionsl = −22→22
3204 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0381P)2 + 0.5817P] where P = (Fo2 + 2Fc2)/3
3204 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

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)

xyzUiso*/Ueq
Fe0.175327 (16)0.49618 (2)0.136596 (10)0.01155 (8)
O1−0.08310 (11)−0.31659 (13)0.38282 (7)0.0288 (3)
O20.09259 (10)−0.23198 (13)0.33170 (7)0.0277 (3)
N10.13730 (11)0.09690 (15)0.31440 (7)0.0173 (2)
N2−0.00760 (11)−0.20171 (15)0.36602 (7)0.0190 (2)
C10.34295 (12)0.55527 (19)0.08304 (8)0.0196 (3)
H10.38490.48760.04910.024*
C20.24330 (13)0.67691 (19)0.06407 (9)0.0219 (3)
H20.20890.70220.01600.026*
C30.20652 (13)0.75263 (18)0.13377 (10)0.0244 (3)
H30.14370.83600.13820.029*
C40.28328 (13)0.67775 (19)0.19565 (9)0.0224 (3)
H40.27880.70420.24640.027*
C50.36735 (12)0.55548 (19)0.16420 (9)0.0195 (3)
H50.42720.48790.19110.023*
C60.13517 (12)0.24086 (17)0.12877 (8)0.0155 (3)
H60.19140.15580.11470.019*
C70.04727 (12)0.33367 (17)0.07798 (8)0.0163 (3)
H70.03730.31990.02610.020*
C8−0.02175 (12)0.45125 (18)0.12293 (8)0.0162 (3)
H8−0.08480.52710.10490.019*
C90.02341 (11)0.43195 (17)0.20148 (8)0.0153 (3)
H9−0.00590.49290.24200.018*
C100.12191 (11)0.30137 (16)0.20541 (8)0.0144 (3)
C110.19956 (12)0.23941 (18)0.27600 (8)0.0173 (3)
H11A0.28460.20370.26190.021*
H11B0.21110.33340.31100.021*
C120.03771 (12)0.11221 (16)0.36170 (7)0.0141 (3)
C13−0.00039 (12)0.27404 (17)0.38947 (8)0.0161 (3)
H130.04170.37090.37350.019*
C14−0.09834 (13)0.29185 (17)0.43954 (8)0.0181 (3)
H14−0.11800.39940.45730.022*
C15−0.16826 (13)0.15031 (18)0.46392 (8)0.0201 (3)
H15−0.23350.16340.49740.024*
C16−0.13745 (14)−0.00804 (16)0.43693 (9)0.0191 (3)
H16−0.1841−0.10250.45140.023*
C17−0.03569 (13)−0.02881 (17)0.38750 (8)0.0157 (3)
H100.1571 (19)−0.001 (2)0.3026 (12)0.028 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe0.01011 (11)0.00982 (11)0.01488 (12)−0.00088 (6)0.00230 (8)0.00070 (6)
O10.0366 (6)0.0115 (5)0.0392 (7)−0.0041 (4)0.0109 (5)0.0019 (4)
O20.0323 (5)0.0169 (5)0.0353 (6)0.0029 (4)0.0149 (5)−0.0029 (4)
N10.0198 (5)0.0129 (6)0.0197 (6)0.0014 (4)0.0052 (4)0.0026 (5)
N20.0242 (6)0.0137 (6)0.0192 (6)0.0005 (5)0.0029 (5)0.0014 (4)
C10.0156 (6)0.0184 (7)0.0256 (8)−0.0041 (5)0.0079 (5)−0.0016 (6)
C20.0188 (6)0.0216 (7)0.0249 (8)−0.0077 (5)−0.0011 (5)0.0106 (6)
C30.0159 (6)0.0108 (6)0.0470 (10)−0.0022 (5)0.0079 (6)0.0012 (6)
C40.0212 (6)0.0227 (7)0.0238 (8)−0.0102 (6)0.0058 (5)−0.0074 (6)
C50.0113 (5)0.0196 (7)0.0274 (8)−0.0040 (5)−0.0004 (5)0.0041 (6)
C60.0153 (6)0.0106 (6)0.0211 (7)−0.0020 (5)0.0037 (5)0.0001 (5)
C70.0154 (6)0.0164 (6)0.0172 (7)−0.0047 (5)0.0007 (5)−0.0006 (5)
C80.0103 (5)0.0154 (6)0.0230 (7)−0.0019 (5)0.0012 (5)0.0034 (5)
C90.0125 (5)0.0144 (6)0.0196 (7)−0.0024 (5)0.0052 (5)0.0008 (5)
C100.0129 (5)0.0128 (6)0.0178 (7)−0.0030 (5)0.0024 (5)0.0026 (5)
C110.0153 (6)0.0185 (7)0.0184 (7)−0.0019 (5)0.0027 (5)0.0039 (5)
C120.0159 (6)0.0129 (6)0.0132 (6)0.0004 (5)−0.0017 (5)0.0021 (5)
C130.0196 (6)0.0109 (6)0.0179 (7)−0.0018 (5)−0.0004 (5)0.0017 (5)
C140.0227 (6)0.0124 (6)0.0189 (7)0.0032 (5)−0.0004 (5)−0.0006 (5)
C150.0218 (6)0.0182 (7)0.0208 (7)0.0036 (5)0.0066 (5)0.0019 (5)
C160.0208 (7)0.0140 (7)0.0229 (8)−0.0007 (5)0.0052 (6)0.0039 (5)
C170.0197 (6)0.0104 (6)0.0169 (7)0.0015 (5)0.0014 (5)0.0016 (5)

Geometric parameters (Å, º)

Fe—C32.0450 (14)C4—H40.9300
Fe—C62.0552 (13)C5—H50.9300
Fe—C102.0562 (13)C6—C71.4466 (19)
Fe—C92.0638 (12)C6—C101.4579 (19)
Fe—C42.0669 (14)C6—H60.9300
Fe—C22.0691 (14)C7—C81.4382 (19)
Fe—C82.0738 (12)C7—H70.9300
Fe—C52.0769 (13)C8—C91.458 (2)
Fe—C12.0776 (13)C8—H80.9300
Fe—C72.0826 (13)C9—C101.4474 (18)
O1—N21.2423 (15)C9—H90.9300
O2—N21.2549 (15)C10—C111.5348 (18)
N1—C121.3711 (17)C11—H11A0.9700
N1—C111.4790 (17)C11—H11B0.9700
N1—H100.830 (18)C12—C131.4292 (18)
N2—C171.4471 (17)C12—C171.4346 (18)
C1—C21.435 (2)C13—C141.3926 (19)
C1—C51.453 (2)C13—H130.9300
C1—H10.9300C14—C151.4096 (19)
C2—C31.445 (2)C14—H140.9300
C2—H20.9300C15—C161.3790 (19)
C3—C41.449 (2)C15—H150.9300
C3—H30.9300C16—C171.4179 (19)
C4—C51.432 (2)C16—H160.9300
C3—Fe—C6174.23 (6)Fe—C3—H3125.6
C3—Fe—C10142.98 (6)C5—C4—C3107.29 (13)
C6—Fe—C1041.54 (5)C5—C4—Fe70.17 (8)
C3—Fe—C9112.44 (6)C3—C4—Fe68.56 (8)
C6—Fe—C968.95 (5)C5—C4—H4126.4
C10—Fe—C941.13 (5)C3—C4—H4126.4
C3—Fe—C441.26 (6)Fe—C4—H4126.5
C6—Fe—C4144.34 (6)C4—C5—C1108.18 (13)
C10—Fe—C4111.60 (6)C4—C5—Fe69.41 (7)
C9—Fe—C4107.04 (6)C1—C5—Fe69.55 (7)
C3—Fe—C241.13 (6)C4—C5—H5125.9
C6—Fe—C2134.76 (6)C1—C5—H5125.9
C10—Fe—C2174.42 (5)Fe—C5—H5126.7
C9—Fe—C2144.32 (6)C7—C6—C10109.39 (11)
C4—Fe—C269.45 (6)C7—C6—Fe70.56 (7)
C3—Fe—C8108.74 (6)C10—C6—Fe69.27 (7)
C6—Fe—C868.34 (5)C7—C6—H6125.3
C10—Fe—C869.41 (5)C10—C6—H6125.3
C9—Fe—C841.27 (5)Fe—C6—H6126.5
C4—Fe—C8132.87 (6)C8—C7—C6107.01 (12)
C2—Fe—C8114.18 (5)C8—C7—Fe69.43 (7)
C3—Fe—C568.49 (6)C6—C7—Fe68.52 (7)
C6—Fe—C5115.06 (6)C8—C7—H7126.5
C10—Fe—C5108.15 (5)C6—C7—H7126.5
C9—Fe—C5132.24 (6)Fe—C7—H7127.1
C4—Fe—C540.42 (6)C7—C8—C9108.81 (12)
C2—Fe—C568.87 (6)C7—C8—Fe70.09 (7)
C8—Fe—C5172.26 (6)C9—C8—Fe69.00 (7)
C3—Fe—C168.33 (6)C7—C8—H8125.6
C6—Fe—C1111.03 (5)C9—C8—H8125.6
C10—Fe—C1134.27 (5)Fe—C8—H8126.9
C9—Fe—C1172.94 (6)C10—C9—C8108.04 (12)
C4—Fe—C168.62 (6)C10—C9—Fe69.15 (7)
C2—Fe—C140.50 (6)C8—C9—Fe69.73 (7)
C8—Fe—C1145.71 (6)C10—C9—H9126.0
C5—Fe—C140.94 (6)C8—C9—H9126.0
C3—Fe—C7133.71 (6)Fe—C9—H9126.7
C6—Fe—C740.92 (5)C9—C10—C6106.74 (11)
C10—Fe—C769.88 (5)C9—C10—C11127.06 (12)
C9—Fe—C769.22 (5)C6—C10—C11126.19 (11)
C4—Fe—C7172.91 (5)C9—C10—Fe69.71 (7)
C2—Fe—C7109.79 (6)C6—C10—Fe69.19 (7)
C8—Fe—C740.49 (5)C11—C10—Fe125.33 (8)
C5—Fe—C7146.44 (6)N1—C11—C10113.36 (10)
C1—Fe—C7115.69 (6)N1—C11—H11A108.9
C12—N1—C11125.30 (12)C10—C11—H11A108.9
C12—N1—H10116.2 (13)N1—C11—H11B108.9
C11—N1—H10118.1 (13)C10—C11—H11B108.9
O1—N2—O2121.78 (12)H11A—C11—H11B107.7
O1—N2—C17118.86 (11)N1—C12—C13121.41 (12)
O2—N2—C17119.36 (11)N1—C12—C17123.88 (12)
C2—C1—C5108.55 (12)C13—C12—C17114.71 (11)
C2—C1—Fe69.43 (7)C14—C13—C12122.34 (12)
C5—C1—Fe69.51 (7)C14—C13—H13118.8
C2—C1—H1125.7C12—C13—H13118.8
C5—C1—H1125.7C13—C14—C15121.41 (12)
Fe—C1—H1126.9C13—C14—H14119.3
C1—C2—C3107.00 (13)C15—C14—H14119.3
C1—C2—Fe70.07 (8)C16—C15—C14118.34 (12)
C3—C2—Fe68.54 (8)C16—C15—H15120.8
C1—C2—H2126.5C14—C15—H15120.8
C3—C2—H2126.5C15—C16—C17120.91 (12)
Fe—C2—H2126.4C15—C16—H16119.5
C2—C3—C4108.99 (12)C17—C16—H16119.5
C2—C3—Fe70.33 (8)C16—C17—C12122.25 (12)
C4—C3—Fe70.18 (8)C16—C17—N2116.03 (11)
C2—C3—H3125.5C12—C17—N2121.70 (12)
C4—C3—H3125.5
C3—Fe—C1—C2−38.48 (9)C3—Fe—C7—C8−64.19 (11)
C6—Fe—C1—C2135.36 (9)C6—Fe—C7—C8118.91 (11)
C10—Fe—C1—C2177.19 (8)C10—Fe—C7—C881.50 (8)
C4—Fe—C1—C2−82.98 (10)C9—Fe—C7—C837.47 (8)
C8—Fe—C1—C253.30 (14)C2—Fe—C7—C8−104.42 (9)
C5—Fe—C1—C2−120.20 (12)C5—Fe—C7—C8174.23 (9)
C7—Fe—C1—C290.87 (9)C1—Fe—C7—C8−148.06 (8)
C3—Fe—C1—C581.72 (9)C3—Fe—C7—C6176.90 (8)
C6—Fe—C1—C5−104.44 (9)C10—Fe—C7—C6−37.40 (7)
C10—Fe—C1—C5−62.61 (11)C9—Fe—C7—C6−81.44 (8)
C4—Fe—C1—C537.21 (9)C2—Fe—C7—C6136.67 (8)
C2—Fe—C1—C5120.20 (12)C8—Fe—C7—C6−118.91 (11)
C8—Fe—C1—C5173.50 (9)C5—Fe—C7—C655.33 (13)
C7—Fe—C1—C5−148.93 (8)C1—Fe—C7—C693.04 (8)
C5—C1—C2—C30.17 (15)C6—C7—C8—C90.16 (14)
Fe—C1—C2—C358.82 (9)Fe—C7—C8—C9−58.25 (9)
C5—C1—C2—Fe−58.65 (9)C6—C7—C8—Fe58.42 (8)
C3—Fe—C2—C1118.47 (12)C3—Fe—C8—C7136.60 (9)
C6—Fe—C2—C1−67.47 (11)C6—Fe—C8—C7−38.09 (8)
C9—Fe—C2—C1171.60 (9)C10—Fe—C8—C7−82.77 (8)
C4—Fe—C2—C180.77 (9)C9—Fe—C8—C7−120.43 (11)
C8—Fe—C2—C1−150.32 (9)C4—Fe—C8—C7176.41 (8)
C5—Fe—C2—C137.38 (9)C2—Fe—C8—C792.62 (9)
C7—Fe—C2—C1−106.74 (9)C1—Fe—C8—C757.81 (13)
C6—Fe—C2—C3174.06 (8)C3—Fe—C8—C9−102.97 (9)
C9—Fe—C2—C353.14 (13)C6—Fe—C8—C982.34 (8)
C4—Fe—C2—C3−37.70 (8)C10—Fe—C8—C937.66 (8)
C8—Fe—C2—C391.21 (9)C4—Fe—C8—C9−63.16 (11)
C5—Fe—C2—C3−81.08 (9)C2—Fe—C8—C9−146.95 (8)
C1—Fe—C2—C3−118.47 (12)C1—Fe—C8—C9178.24 (9)
C7—Fe—C2—C3134.79 (8)C7—Fe—C8—C9120.43 (11)
C1—C2—C3—C4−0.05 (15)C7—C8—C9—C100.20 (14)
Fe—C2—C3—C459.75 (9)Fe—C8—C9—C10−58.72 (8)
C1—C2—C3—Fe−59.79 (9)C7—C8—C9—Fe58.92 (9)
C10—Fe—C3—C2174.00 (8)C3—Fe—C9—C10−147.17 (8)
C9—Fe—C3—C2−149.68 (8)C6—Fe—C9—C1038.87 (8)
C4—Fe—C3—C2119.75 (11)C4—Fe—C9—C10−103.56 (8)
C8—Fe—C3—C2−105.61 (9)C2—Fe—C9—C10178.13 (9)
C5—Fe—C3—C282.08 (9)C8—Fe—C9—C10119.60 (11)
C1—Fe—C3—C237.90 (8)C5—Fe—C9—C10−66.42 (10)
C7—Fe—C3—C2−67.50 (10)C7—Fe—C9—C1082.82 (8)
C10—Fe—C3—C454.25 (12)C3—Fe—C9—C893.23 (9)
C9—Fe—C3—C490.58 (8)C6—Fe—C9—C8−80.73 (8)
C2—Fe—C3—C4−119.75 (11)C10—Fe—C9—C8−119.60 (11)
C8—Fe—C3—C4134.64 (8)C4—Fe—C9—C8136.84 (8)
C5—Fe—C3—C4−37.66 (8)C2—Fe—C9—C858.53 (13)
C1—Fe—C3—C4−81.85 (9)C5—Fe—C9—C8173.98 (8)
C7—Fe—C3—C4172.75 (7)C7—Fe—C9—C8−36.78 (8)
C2—C3—C4—C5−0.10 (15)C8—C9—C10—C6−0.48 (13)
Fe—C3—C4—C559.74 (9)Fe—C9—C10—C6−59.56 (8)
C2—C3—C4—Fe−59.84 (9)C8—C9—C10—C11178.65 (11)
C3—Fe—C4—C5−118.75 (12)Fe—C9—C10—C11119.57 (12)
C6—Fe—C4—C558.96 (13)C8—C9—C10—Fe59.08 (9)
C10—Fe—C4—C592.96 (9)C7—C6—C10—C90.59 (14)
C9—Fe—C4—C5136.42 (8)Fe—C6—C10—C959.89 (8)
C2—Fe—C4—C5−81.17 (9)C7—C6—C10—C11−178.55 (11)
C8—Fe—C4—C5174.41 (8)Fe—C6—C10—C11−119.25 (12)
C1—Fe—C4—C5−37.67 (9)C7—C6—C10—Fe−59.30 (9)
C6—Fe—C4—C3177.71 (8)C3—Fe—C10—C956.33 (12)
C10—Fe—C4—C3−148.29 (8)C6—Fe—C10—C9−117.97 (11)
C9—Fe—C4—C3−104.83 (8)C4—Fe—C10—C991.48 (8)
C2—Fe—C4—C337.58 (8)C8—Fe—C10—C9−37.78 (8)
C8—Fe—C4—C3−66.84 (11)C5—Fe—C10—C9134.43 (8)
C5—Fe—C4—C3118.75 (12)C1—Fe—C10—C9172.19 (8)
C1—Fe—C4—C381.08 (9)C7—Fe—C10—C9−81.10 (8)
C3—C4—C5—C10.21 (15)C3—Fe—C10—C6174.30 (8)
Fe—C4—C5—C158.93 (9)C9—Fe—C10—C6117.97 (11)
C3—C4—C5—Fe−58.72 (9)C4—Fe—C10—C6−150.56 (7)
C2—C1—C5—C4−0.24 (15)C8—Fe—C10—C680.18 (8)
Fe—C1—C5—C4−58.84 (9)C5—Fe—C10—C6−107.60 (8)
C2—C1—C5—Fe58.60 (9)C1—Fe—C10—C6−69.85 (10)
C3—Fe—C5—C438.42 (9)C7—Fe—C10—C636.87 (7)
C6—Fe—C5—C4−146.53 (9)C3—Fe—C10—C11−65.38 (14)
C10—Fe—C5—C4−102.28 (9)C6—Fe—C10—C11120.33 (14)
C9—Fe—C5—C4−62.91 (11)C9—Fe—C10—C11−121.71 (14)
C2—Fe—C5—C482.72 (9)C4—Fe—C10—C11−30.23 (12)
C1—Fe—C5—C4119.71 (12)C8—Fe—C10—C11−159.49 (12)
C7—Fe—C5—C4176.98 (10)C5—Fe—C10—C1112.73 (12)
C3—Fe—C5—C1−81.29 (9)C1—Fe—C10—C1150.48 (14)
C6—Fe—C5—C193.75 (9)C7—Fe—C10—C11157.20 (12)
C10—Fe—C5—C1138.00 (8)C12—N1—C11—C10−79.74 (16)
C9—Fe—C5—C1177.38 (8)C9—C10—C11—N189.84 (16)
C4—Fe—C5—C1−119.71 (12)C6—C10—C11—N1−91.19 (15)
C2—Fe—C5—C1−36.99 (9)Fe—C10—C11—N1180.00 (9)
C7—Fe—C5—C157.26 (13)C11—N1—C12—C13−11.7 (2)
C10—Fe—C6—C7120.67 (10)C11—N1—C12—C17168.50 (13)
C9—Fe—C6—C782.17 (8)N1—C12—C13—C14−177.79 (13)
C4—Fe—C6—C7172.30 (8)C17—C12—C13—C141.99 (19)
C2—Fe—C6—C7−65.41 (10)C12—C13—C14—C15−1.9 (2)
C8—Fe—C6—C737.70 (8)C13—C14—C15—C160.0 (2)
C5—Fe—C6—C7−149.87 (8)C14—C15—C16—C171.7 (2)
C1—Fe—C6—C7−105.40 (8)C15—C16—C17—C12−1.6 (2)
C9—Fe—C6—C10−38.50 (7)C15—C16—C17—N2176.83 (13)
C4—Fe—C6—C1051.63 (12)N1—C12—C17—C16179.49 (13)
C2—Fe—C6—C10173.92 (7)C13—C12—C17—C16−0.3 (2)
C8—Fe—C6—C10−82.97 (8)N1—C12—C17—N21.2 (2)
C5—Fe—C6—C1089.46 (8)C13—C12—C17—N2−178.58 (12)
C1—Fe—C6—C10133.93 (8)O1—N2—C17—C169.75 (19)
C7—Fe—C6—C10−120.67 (10)O2—N2—C17—C16−169.57 (13)
C10—C6—C7—C8−0.47 (14)O1—N2—C17—C12−171.86 (13)
Fe—C6—C7—C8−58.99 (9)O2—N2—C17—C128.8 (2)
C10—C6—C7—Fe58.52 (9)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
N1—H10···O20.827 (16)2.01 (2)2.6511 (19)133.3 (18)
N1—H10···N20.827 (16)2.624 (19)2.961 (2)106.0 (16)
C4—H4···O2i0.932.573.283 (2)134
C16—H16···O10.932.362.683 (2)100

Symmetry code: (i) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2180).

References

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