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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m49.
Published online 2009 December 12. doi:  10.1107/S1600536809051216
PMCID: PMC2980222

1-(4-Ferrocenylphen­yl)-3-methyl­imidazolium iodide monohydrate

Abstract

In the title compound, [Fe(C5H5)(C15H14N2)]I·H2O, the benzene and imidazolium rings are twisted by 17.26 (17) and 32.53 (19)°, respectively, with respect to the η5-C5H4 plane of the ferrocenyl unit. The imidazolium ring is rotated by 48.81 (17)° with respect to the benzene ring. The packing is dominated by layers established by O—H(...)I, C—H(...)I and C—H(...)O contacts and propagating along the bc plane.

Related literature

For imidazolium salts see: Nolan et al. (2007 [triangle]); Cheng et al. (2008 [triangle]); Yang et al. (2009 [triangle]); Bildstein et al. (1999 [triangle]). For the synthesis, see: Zhao et al. (2001 [triangle]); Koten et al. (2007 [triangle]). For graph-set analysis, see: Bernstein et al. (1995 [triangle]); Etter et al. (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00m49-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C15H14N2)]I·H2O
  • M r = 488.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00m49-efi1.jpg
  • a = 17.3871 (7) Å
  • b = 7.3397 (2) Å
  • c = 16.9445 (6) Å
  • β = 117.299 (5)°
  • V = 1921.56 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.40 mm−1
  • T = 200 K
  • 0.50 × 0.39 × 0.04 mm

Data collection

  • Oxford Xcalibur diffractometer
  • Absorption correction: numerical [X-SHAPE (Stoe & Cie, 1996 [triangle]) and X-RED (Stoe & Cie, 1997 [triangle])] T min = 0.399, T max = 0.901
  • 12113 measured reflections
  • 3885 independent reflections
  • 3098 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.081
  • S = 0.97
  • 3885 reflections
  • 227 parameters
  • H-atom parameters constrained
  • Δρmax = 1.28 e Å−3
  • Δρmin = −0.50 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051216/ng2694sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051216/ng2694Isup2.hkl

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

Acknowledgments

Financial support by Nelson Mandela Metropolitan University is gratefully acknowledged, as is Professor P. Klüfers for generous allocation of diffractometer time.

supplementary crystallographic information

Comment

The structure consists of a ferrocenyl group attached to a phenyl-imidazolium moiety in para-position, an iodide anion and a water molecule (Fig. 1). The phenyl ring A is twisted by 17.26 (17)° away from the least-square plane B of the cyclopentadienyl ring, and by 48.81 (17)° from the imidazole ring C. The plane of the imidazole unit C is rotated by 32.53 (19)° with respect to the η5-C5H4 plane A (for plane definition, see Table 2).

The packing of the title compound is dominated by two-dimensional layers parallel to the bc plane formed by O–H···I, C–H···I and C–H···O contacts (Fig. 2). Eight-membered rings consisting of two water molecules and two iodide anions are formed by four O–H···I contacts. According to graph-set theory (Bernstein et al. 1995; Etter et al. 1990), the descriptor R42(8) can be assigned on the binary level for these rings. Additionally each of the two oxygen and the two iodide atoms of the rings acts as an acceptor in C–H···O/I contacts to four different imidazole moieties.

The packing of the title compound viewed along [010] is shown in Figure 3.

Experimental

All chemicals used (reagent grade) were commercially available. 4-Bromophenylferrocene (Zhao et al. 2001) and 4-ferrocenylphenyl-1H-imidazole (Koten et al. 2007) were prepared according to literature methods. In a round- bottomed flask, iodomethane (5 ml) was added to 4-ferrocenylphenyl-1H-imidzole and allowed to reflux gently under a nitrogen atmosphere for 3 h. The reaction was monitored visually, and the yellow colour of the solution gradually turned colourless, signaling the completion of the reaction. After cooling, the yellow precipitate was filtered off under vacuum and washed with ether (yield, 99%). Recrystallization was from a dichloromethane/toluene mixture. M.p. 130–132°C, IR (KBr cm-1): 3463, 3403, 3080, 1616, 1554, 1455, 1262, 1222, 1003, 887, 823, 751; 1H NMR (300 MHz, CDCl3); 10.64 (1H, s, ImH), 7.65–7.69 (6H, m, 4×ArH, 2×ImH), 4.69 (2H, t, J 1.9, C5H4), 4.42 (2H. t, J 1.9, C5H4), 4.28 (3H, s, CH3), 4.07 (5H, s, C5H5); 13C NMR 134.02, 135.70, 131.60, 127.64, 124.19, 122.07, 120.48, 82.39, 69.94, 69.88, 66.81, 37.66.

Refinement

The C-bound H atoms are riding on their parent atoms (C—H = 0.98 Å for CH3, 0.95 Å for CH) with Uiso(H) = 1.2Ueq(C) for CH, Uiso(H) = 1.5Ueq(C) for CH3]. The O-bound H are riding on their parent atom (O—H = 0.84 Å) with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound (anisotropic displacement ellipsoids drawn at the 50% probability level).
Fig. 2.
two-dimensional layer propagating along the bc plane. Red dotted lines indicate O–H···I contacts, blue dotted lines indicate C–H···O and C–H···I contacts. ...
Fig. 3.
The packing of the title compound viewed along [010].

Crystal data

[Fe(C5H5)(C15H14N2)]I·H2OF(000) = 968
Mr = 488.14Dx = 1.687 (1) Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6938 reflections
a = 17.3871 (7) Åθ = 4.4–26.3°
b = 7.3397 (2) ŵ = 2.40 mm1
c = 16.9445 (6) ÅT = 200 K
β = 117.299 (5)°Platelet, orange
V = 1921.56 (14) Å30.50 × 0.39 × 0.04 mm
Z = 4

Data collection

Oxford Xcalibur diffractometer3885 independent reflections
Radiation source: fine-focus sealed tube3098 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 15.9809 pixels mm-1θmax = 26.4°, θmin = 4.5°
ω scansh = −21→19
Absorption correction: numerical [X-SHAPE (Stoe & Cie, 1996) and X-RED (Stoe & Cie, 1997)]k = −9→9
Tmin = 0.399, Tmax = 0.901l = −16→21
12113 measured 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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3
3885 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 1.28 e Å3
0 restraintsΔρmin = −0.50 e Å3

Special details

Experimental. Crystal faces optimized with XShape, Version 1.02 (Stoe, 1996) Absorption correction with XRed, Version 1.09 (Stoe, 1997)
Refinement. The C-bound H atoms are riding on their parent atoms (C—H = 0.98 Å for CH3, 0.95 Å for CH) with Uiso(H) = 1.2Ueq(C) for CH, Uiso(H) = 1.5Ueq(C) for CH3]. The O-bound H are riding on their parent atom (O—H = 0.84 Å) with Uiso(H) = 1.5Ueq(O).

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

xyzUiso*/Ueq
Fe10.63876 (3)0.84486 (5)0.20164 (3)0.02466 (12)
N10.18768 (18)0.6660 (3)−0.07900 (16)0.0282 (6)
N20.04809 (19)0.6670 (3)−0.13933 (19)0.0364 (7)
C10.5395 (2)0.6743 (4)0.18554 (19)0.0235 (6)
C20.5720 (2)0.7706 (4)0.26899 (19)0.0263 (6)
H20.53950.84880.28700.032*
C30.6614 (2)0.7277 (4)0.3194 (2)0.0320 (7)
H30.69890.77260.37700.038*
C40.6848 (2)0.6060 (4)0.2687 (2)0.0330 (7)
H40.74060.55550.28640.040*
C50.6103 (2)0.5735 (4)0.1875 (2)0.0287 (7)
H50.60780.49640.14140.034*
C60.4495 (2)0.6764 (4)0.11489 (19)0.0226 (6)
C70.3910 (2)0.8094 (4)0.1133 (2)0.0265 (7)
H70.41070.90280.15690.032*
C80.3054 (2)0.8078 (4)0.0495 (2)0.0279 (7)
H80.26680.90000.04880.034*
C90.2766 (2)0.6703 (4)−0.01333 (19)0.0253 (6)
C100.3324 (2)0.5365 (4)−0.01372 (19)0.0295 (7)
H100.31210.4425−0.05710.035*
C110.4182 (2)0.5411 (4)0.04971 (19)0.0288 (7)
H11A0.45670.45020.04900.035*
C120.1202 (2)0.6788 (4)−0.0630 (2)0.0295 (7)
H12A0.12280.6940−0.00610.035*
C130.0705 (3)0.6437 (5)−0.2066 (2)0.0423 (9)
H130.03150.6302−0.26790.051*
C140.1569 (2)0.6435 (5)−0.1704 (2)0.0359 (8)
H140.19080.6305−0.20090.043*
C15−0.0396 (3)0.6651 (6)−0.1483 (3)0.0570 (11)
H15A−0.06730.5483−0.17350.085*
H15B−0.07330.7644−0.18770.085*
H15C−0.03710.6814−0.08980.085*
C160.6389 (3)1.1210 (5)0.2001 (3)0.0510 (11)
H160.61801.19740.23120.061*
C170.7237 (3)1.0564 (5)0.2324 (3)0.0541 (11)
H170.77061.08140.28910.065*
C180.7271 (3)0.9470 (5)0.1652 (3)0.0483 (9)
H180.77660.88440.16930.058*
C190.6455 (2)0.9471 (4)0.0923 (2)0.0375 (8)
H190.63000.88620.03770.045*
C200.5897 (3)1.0525 (4)0.1130 (2)0.0427 (9)
H200.53001.07390.07550.051*
O10.11333 (17)0.8580 (4)0.11076 (16)0.0511 (7)
H1A0.06110.84250.09800.077*
H1B0.11590.93490.07530.077*
I1−0.112089 (15)0.80931 (3)0.047195 (15)0.04024 (10)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0253 (2)0.0217 (2)0.0259 (2)−0.00069 (16)0.01074 (19)0.00191 (17)
N10.0316 (15)0.0281 (14)0.0238 (13)−0.0031 (11)0.0117 (12)0.0003 (10)
N20.0327 (16)0.0341 (15)0.0361 (15)0.0009 (12)0.0104 (13)−0.0007 (12)
C10.0322 (18)0.0182 (14)0.0226 (14)−0.0026 (11)0.0146 (13)0.0007 (11)
C20.0317 (18)0.0247 (15)0.0251 (15)−0.0015 (12)0.0153 (14)−0.0009 (12)
C30.0318 (19)0.0350 (17)0.0236 (15)−0.0044 (14)0.0079 (14)0.0038 (13)
C40.0300 (18)0.0261 (16)0.0416 (18)0.0066 (13)0.0154 (16)0.0080 (14)
C50.0363 (18)0.0218 (15)0.0309 (16)−0.0003 (13)0.0179 (15)0.0031 (13)
C60.0289 (17)0.0201 (14)0.0226 (14)−0.0032 (11)0.0150 (13)0.0006 (11)
C70.0297 (17)0.0236 (15)0.0266 (15)−0.0003 (12)0.0132 (14)−0.0040 (12)
C80.0321 (18)0.0239 (15)0.0299 (16)0.0011 (12)0.0160 (14)−0.0029 (12)
C90.0285 (17)0.0260 (15)0.0211 (14)−0.0048 (12)0.0111 (13)0.0007 (11)
C100.0374 (19)0.0261 (16)0.0259 (15)−0.0031 (13)0.0153 (14)−0.0081 (12)
C110.0350 (18)0.0241 (15)0.0317 (16)0.0008 (13)0.0190 (15)−0.0036 (12)
C120.0296 (18)0.0301 (18)0.0273 (16)0.0016 (12)0.0118 (14)−0.0020 (12)
C130.046 (2)0.045 (2)0.0262 (17)−0.0032 (16)0.0088 (17)−0.0016 (15)
C140.040 (2)0.0430 (19)0.0221 (15)−0.0068 (15)0.0123 (15)−0.0038 (14)
C150.029 (2)0.069 (3)0.063 (3)0.0035 (18)0.013 (2)−0.008 (2)
C160.089 (4)0.0171 (16)0.062 (3)−0.0045 (18)0.048 (3)−0.0013 (16)
C170.058 (3)0.049 (2)0.045 (2)−0.028 (2)0.015 (2)−0.0007 (18)
C180.041 (2)0.051 (2)0.057 (2)−0.0043 (17)0.025 (2)0.0150 (19)
C190.051 (2)0.0315 (18)0.0346 (18)−0.0023 (15)0.0230 (17)0.0072 (14)
C200.044 (2)0.0325 (18)0.046 (2)0.0065 (15)0.0164 (18)0.0181 (15)
O10.0404 (16)0.0708 (17)0.0442 (14)0.0056 (13)0.0213 (13)0.0096 (13)
I10.03337 (15)0.03911 (15)0.03887 (15)−0.00048 (9)0.00850 (11)0.00466 (9)

Geometric parameters (Å, °)

Fe1—C162.027 (3)C7—C81.381 (4)
Fe1—C202.032 (3)C7—H70.9500
Fe1—C172.039 (4)C8—C91.383 (4)
Fe1—C32.039 (3)C8—H80.9500
Fe1—C52.040 (3)C9—C101.384 (4)
Fe1—C22.040 (3)C10—C111.382 (4)
Fe1—C182.042 (4)C10—H100.9500
Fe1—C42.042 (3)C11—H11A0.9500
Fe1—C12.046 (3)C12—H12A0.9500
Fe1—C192.052 (3)C13—C141.337 (5)
N1—C121.323 (4)C13—H130.9500
N1—C141.397 (4)C14—H140.9500
N1—C91.432 (4)C15—H15A0.9800
N2—C121.328 (4)C15—H15B0.9800
N2—C131.374 (5)C15—H15C0.9800
N2—C151.461 (5)C16—C171.399 (6)
C1—C51.424 (4)C16—C201.416 (5)
C1—C21.444 (4)C16—H160.9486
C1—C61.472 (4)C17—C181.416 (5)
C2—C31.423 (4)C17—H170.9503
C2—H20.9490C18—C191.390 (5)
C3—C41.423 (5)C18—H180.9496
C3—H30.9500C19—C201.407 (5)
C4—C51.411 (4)C19—H190.9485
C4—H40.9496C20—H200.9492
C5—H50.9493O1—H1A0.8400
C6—C111.397 (4)O1—H1B0.8400
C6—C71.400 (4)
C16—Fe1—C2040.82 (15)C3—C4—H4126.0
C16—Fe1—C1740.26 (17)Fe1—C4—H4126.4
C20—Fe1—C1768.09 (16)C4—C5—C1109.4 (3)
C16—Fe1—C3115.66 (14)C4—C5—Fe169.87 (17)
C20—Fe1—C3150.05 (15)C1—C5—Fe169.85 (16)
C17—Fe1—C3106.21 (14)C4—C5—H5125.3
C16—Fe1—C5167.57 (17)C1—C5—H5125.3
C20—Fe1—C5130.44 (14)Fe1—C5—H5126.6
C17—Fe1—C5151.86 (16)C11—C6—C7117.7 (3)
C3—Fe1—C568.33 (13)C11—C6—C1121.3 (3)
C16—Fe1—C2106.16 (14)C7—C6—C1121.0 (2)
C20—Fe1—C2117.37 (14)C8—C7—C6121.4 (3)
C17—Fe1—C2126.28 (15)C8—C7—H7119.3
C3—Fe1—C240.85 (13)C6—C7—H7119.3
C5—Fe1—C268.62 (12)C7—C8—C9119.3 (3)
C16—Fe1—C1867.90 (17)C7—C8—H8120.4
C20—Fe1—C1867.70 (15)C9—C8—H8120.4
C17—Fe1—C1840.60 (16)C8—C9—C10120.9 (3)
C3—Fe1—C18128.05 (15)C8—C9—N1119.7 (3)
C5—Fe1—C18119.89 (15)C10—C9—N1119.4 (3)
C2—Fe1—C18165.18 (14)C11—C10—C9119.2 (3)
C16—Fe1—C4149.65 (16)C11—C10—H10120.4
C20—Fe1—C4168.37 (14)C9—C10—H10120.4
C17—Fe1—C4117.31 (15)C10—C11—C6121.5 (3)
C3—Fe1—C440.79 (13)C10—C11—H11A119.3
C5—Fe1—C440.45 (12)C6—C11—H11A119.3
C2—Fe1—C468.75 (13)N1—C12—N2109.0 (3)
C18—Fe1—C4109.05 (15)N1—C12—H12A125.5
C16—Fe1—C1127.99 (16)N2—C12—H12A125.5
C20—Fe1—C1108.52 (13)C14—C13—N2107.8 (3)
C17—Fe1—C1165.36 (16)C14—C13—H13126.1
C3—Fe1—C169.20 (12)N2—C13—H13126.1
C5—Fe1—C140.79 (12)C13—C14—N1106.7 (3)
C2—Fe1—C141.39 (11)C13—C14—H14126.7
C18—Fe1—C1152.79 (14)N1—C14—H14126.7
C4—Fe1—C168.92 (12)N2—C15—H15A109.5
C16—Fe1—C1967.81 (14)N2—C15—H15B109.5
C20—Fe1—C1940.28 (14)H15A—C15—H15B109.5
C17—Fe1—C1967.52 (15)N2—C15—H15C109.5
C3—Fe1—C19166.65 (14)H15A—C15—H15C109.5
C5—Fe1—C19111.23 (13)H15B—C15—H15C109.5
C2—Fe1—C19152.35 (14)C17—C16—C20108.1 (3)
C18—Fe1—C1939.69 (14)C17—C16—Fe170.3 (2)
C4—Fe1—C19130.26 (13)C20—C16—Fe169.78 (19)
C1—Fe1—C19119.82 (13)C17—C16—H16125.9
C12—N1—C14108.1 (3)C20—C16—H16125.9
C12—N1—C9125.6 (3)Fe1—C16—H16125.5
C14—N1—C9126.3 (3)C16—C17—C18107.7 (4)
C12—N2—C13108.4 (3)C16—C17—Fe169.4 (2)
C12—N2—C15125.2 (3)C18—C17—Fe169.8 (2)
C13—N2—C15126.3 (3)C16—C17—H17126.2
C5—C1—C2106.6 (3)C18—C17—H17126.1
C5—C1—C6127.6 (3)Fe1—C17—H17126.2
C2—C1—C6125.7 (3)C19—C18—C17108.2 (4)
C5—C1—Fe169.36 (17)C19—C18—Fe170.5 (2)
C2—C1—Fe169.07 (17)C17—C18—Fe169.6 (2)
C6—C1—Fe1128.30 (19)C19—C18—H18125.9
C3—C2—C1108.0 (3)C17—C18—H18125.9
C3—C2—Fe169.55 (18)Fe1—C18—H18125.6
C1—C2—Fe169.54 (17)C18—C19—C20108.5 (3)
C3—C2—H2126.0C18—C19—Fe169.76 (19)
C1—C2—H2126.0C20—C19—Fe169.10 (18)
Fe1—C2—H2126.5C18—C19—H19125.8
C4—C3—C2108.2 (3)C20—C19—H19125.7
C4—C3—Fe169.73 (17)Fe1—C19—H19126.9
C2—C3—Fe169.60 (17)C19—C20—C16107.5 (3)
C4—C3—H3126.0C19—C20—Fe170.61 (19)
C2—C3—H3125.9C16—C20—Fe169.39 (19)
Fe1—C3—H3126.4C19—C20—H20126.3
C5—C4—C3107.9 (3)C16—C20—H20126.3
C5—C4—Fe169.68 (17)Fe1—C20—H20125.3
C3—C4—Fe169.48 (17)H1A—O1—H1B108.3
C5—C4—H4126.1
C16—Fe1—C1—C5172.5 (2)C6—C7—C8—C90.9 (5)
C20—Fe1—C1—C5131.22 (19)C7—C8—C9—C10−0.8 (4)
C17—Fe1—C1—C5−154.7 (5)C7—C8—C9—N1179.2 (3)
C3—Fe1—C1—C5−80.54 (19)C12—N1—C9—C8−49.9 (4)
C2—Fe1—C1—C5−118.1 (2)C14—N1—C9—C8131.7 (3)
C18—Fe1—C1—C554.2 (4)C12—N1—C9—C10130.1 (3)
C4—Fe1—C1—C5−36.71 (18)C14—N1—C9—C10−48.3 (4)
C19—Fe1—C1—C588.6 (2)C8—C9—C10—C110.0 (4)
C16—Fe1—C1—C2−69.4 (2)N1—C9—C10—C11180.0 (3)
C20—Fe1—C1—C2−110.69 (19)C9—C10—C11—C60.8 (4)
C17—Fe1—C1—C2−36.6 (6)C7—C6—C11—C10−0.8 (4)
C3—Fe1—C1—C237.55 (18)C1—C6—C11—C10176.2 (3)
C5—Fe1—C1—C2118.1 (2)C14—N1—C12—N2−0.4 (3)
C18—Fe1—C1—C2172.2 (3)C9—N1—C12—N2−179.1 (2)
C4—Fe1—C1—C281.37 (19)C13—N2—C12—N10.7 (4)
C19—Fe1—C1—C2−153.36 (18)C15—N2—C12—N1176.4 (3)
C16—Fe1—C1—C650.3 (3)C12—N2—C13—C14−0.6 (4)
C20—Fe1—C1—C69.0 (3)C15—N2—C13—C14−176.3 (3)
C17—Fe1—C1—C683.0 (6)N2—C13—C14—N10.3 (4)
C3—Fe1—C1—C6157.2 (3)C12—N1—C14—C130.1 (4)
C5—Fe1—C1—C6−122.3 (3)C9—N1—C14—C13178.7 (3)
C2—Fe1—C1—C6119.7 (3)C20—Fe1—C16—C17−118.9 (3)
C18—Fe1—C1—C6−68.1 (4)C3—Fe1—C16—C1784.9 (3)
C4—Fe1—C1—C6−159.0 (3)C5—Fe1—C16—C17−169.0 (6)
C19—Fe1—C1—C6−33.7 (3)C2—Fe1—C16—C17127.7 (2)
C5—C1—C2—C30.4 (3)C18—Fe1—C16—C17−37.9 (2)
C6—C1—C2—C3178.1 (3)C4—Fe1—C16—C1752.3 (4)
Fe1—C1—C2—C3−59.1 (2)C1—Fe1—C16—C17167.8 (2)
C5—C1—C2—Fe159.49 (19)C19—Fe1—C16—C17−80.9 (3)
C6—C1—C2—Fe1−122.8 (3)C17—Fe1—C16—C20118.9 (3)
C16—Fe1—C2—C3−110.7 (2)C3—Fe1—C16—C20−156.1 (2)
C20—Fe1—C2—C3−153.3 (2)C5—Fe1—C16—C20−50.1 (8)
C17—Fe1—C2—C3−71.4 (2)C2—Fe1—C16—C20−113.4 (2)
C5—Fe1—C2—C381.2 (2)C18—Fe1—C16—C2081.0 (2)
C18—Fe1—C2—C3−46.6 (6)C4—Fe1—C16—C20171.2 (3)
C4—Fe1—C2—C337.61 (19)C1—Fe1—C16—C20−73.3 (3)
C1—Fe1—C2—C3119.4 (3)C19—Fe1—C16—C2038.0 (2)
C19—Fe1—C2—C3176.4 (3)C20—C16—C17—C18−0.2 (4)
C16—Fe1—C2—C1129.8 (2)Fe1—C16—C17—C1859.6 (2)
C20—Fe1—C2—C187.3 (2)C20—C16—C17—Fe1−59.8 (2)
C17—Fe1—C2—C1169.2 (2)C20—Fe1—C17—C1638.1 (2)
C3—Fe1—C2—C1−119.4 (3)C3—Fe1—C17—C16−110.8 (2)
C5—Fe1—C2—C1−38.24 (17)C5—Fe1—C17—C16175.0 (3)
C18—Fe1—C2—C1−166.0 (5)C2—Fe1—C17—C16−70.6 (3)
C4—Fe1—C2—C1−81.81 (18)C18—Fe1—C17—C16118.9 (3)
C19—Fe1—C2—C157.0 (3)C4—Fe1—C17—C16−153.3 (2)
C1—C2—C3—C4−0.2 (3)C1—Fe1—C17—C16−41.3 (7)
Fe1—C2—C3—C4−59.3 (2)C19—Fe1—C17—C1681.7 (2)
C1—C2—C3—Fe159.1 (2)C16—Fe1—C17—C18−118.9 (3)
C16—Fe1—C3—C4−155.3 (2)C20—Fe1—C17—C18−80.8 (2)
C20—Fe1—C3—C4172.7 (3)C3—Fe1—C17—C18130.3 (2)
C17—Fe1—C3—C4−113.2 (2)C5—Fe1—C17—C1856.1 (4)
C5—Fe1—C3—C437.54 (19)C2—Fe1—C17—C18170.5 (2)
C2—Fe1—C3—C4119.5 (3)C4—Fe1—C17—C1887.8 (2)
C18—Fe1—C3—C4−74.2 (3)C1—Fe1—C17—C18−160.2 (5)
C1—Fe1—C3—C481.4 (2)C19—Fe1—C17—C18−37.2 (2)
C19—Fe1—C3—C4−53.2 (6)C16—C17—C18—C190.9 (4)
C16—Fe1—C3—C285.2 (2)Fe1—C17—C18—C1960.2 (2)
C20—Fe1—C3—C253.2 (4)C16—C17—C18—Fe1−59.3 (3)
C17—Fe1—C3—C2127.3 (2)C16—Fe1—C18—C19−81.4 (2)
C5—Fe1—C3—C2−81.93 (19)C20—Fe1—C18—C19−37.2 (2)
C18—Fe1—C3—C2166.3 (2)C17—Fe1—C18—C19−119.1 (3)
C4—Fe1—C3—C2−119.5 (3)C3—Fe1—C18—C19172.6 (2)
C1—Fe1—C3—C2−38.03 (17)C5—Fe1—C18—C1987.8 (2)
C19—Fe1—C3—C2−172.7 (5)C2—Fe1—C18—C19−150.3 (5)
C2—C3—C4—C5−0.1 (3)C4—Fe1—C18—C19130.9 (2)
Fe1—C3—C4—C5−59.3 (2)C1—Fe1—C18—C1950.1 (4)
C2—C3—C4—Fe159.2 (2)C16—Fe1—C18—C1737.6 (2)
C16—Fe1—C4—C5167.4 (3)C20—Fe1—C18—C1781.9 (2)
C20—Fe1—C4—C5−42.3 (8)C3—Fe1—C18—C17−68.4 (3)
C17—Fe1—C4—C5−157.5 (2)C5—Fe1—C18—C17−153.2 (2)
C3—Fe1—C4—C5119.2 (3)C2—Fe1—C18—C17−31.2 (7)
C2—Fe1—C4—C581.6 (2)C4—Fe1—C18—C17−110.1 (2)
C18—Fe1—C4—C5−114.1 (2)C1—Fe1—C18—C17169.2 (3)
C1—Fe1—C4—C537.02 (18)C19—Fe1—C18—C17119.1 (3)
C19—Fe1—C4—C5−74.8 (2)C17—C18—C19—C20−1.2 (4)
C16—Fe1—C4—C348.1 (4)Fe1—C18—C19—C2058.4 (2)
C20—Fe1—C4—C3−161.6 (7)C17—C18—C19—Fe1−59.6 (2)
C17—Fe1—C4—C383.3 (2)C16—Fe1—C19—C1881.7 (3)
C5—Fe1—C4—C3−119.2 (3)C20—Fe1—C19—C18120.2 (3)
C2—Fe1—C4—C3−37.66 (18)C17—Fe1—C19—C1838.0 (2)
C18—Fe1—C4—C3126.7 (2)C3—Fe1—C19—C18−26.2 (7)
C1—Fe1—C4—C3−82.2 (2)C5—Fe1—C19—C18−111.7 (2)
C19—Fe1—C4—C3166.0 (2)C2—Fe1—C19—C18164.2 (3)
C3—C4—C5—C10.4 (3)C4—Fe1—C19—C18−69.5 (3)
Fe1—C4—C5—C1−58.8 (2)C1—Fe1—C19—C18−156.1 (2)
C3—C4—C5—Fe159.2 (2)C16—Fe1—C19—C20−38.5 (2)
C2—C1—C5—C4−0.5 (3)C17—Fe1—C19—C20−82.2 (2)
C6—C1—C5—C4−178.1 (3)C3—Fe1—C19—C20−146.3 (5)
Fe1—C1—C5—C458.8 (2)C5—Fe1—C19—C20128.2 (2)
C2—C1—C5—Fe1−59.30 (19)C2—Fe1—C19—C2044.0 (4)
C6—C1—C5—Fe1123.1 (3)C18—Fe1—C19—C20−120.2 (3)
C16—Fe1—C5—C4−149.1 (6)C4—Fe1—C19—C20170.4 (2)
C20—Fe1—C5—C4169.7 (2)C1—Fe1—C19—C2083.7 (2)
C17—Fe1—C5—C446.1 (4)C18—C19—C20—C161.1 (4)
C3—Fe1—C5—C4−37.85 (19)Fe1—C19—C20—C1659.9 (2)
C2—Fe1—C5—C4−81.9 (2)C18—C19—C20—Fe1−58.8 (2)
C18—Fe1—C5—C484.6 (2)C17—C16—C20—C19−0.5 (4)
C1—Fe1—C5—C4−120.7 (3)Fe1—C16—C20—C19−60.7 (2)
C19—Fe1—C5—C4127.8 (2)C17—C16—C20—Fe160.1 (2)
C16—Fe1—C5—C1−28.4 (7)C16—Fe1—C20—C19118.2 (3)
C20—Fe1—C5—C1−69.6 (2)C17—Fe1—C20—C1980.6 (2)
C17—Fe1—C5—C1166.8 (3)C3—Fe1—C20—C19165.1 (3)
C3—Fe1—C5—C182.85 (19)C5—Fe1—C20—C19−74.4 (3)
C2—Fe1—C5—C138.79 (17)C2—Fe1—C20—C19−158.7 (2)
C18—Fe1—C5—C1−154.69 (19)C18—Fe1—C20—C1936.6 (2)
C4—Fe1—C5—C1120.7 (3)C4—Fe1—C20—C19−39.3 (8)
C19—Fe1—C5—C1−111.49 (19)C1—Fe1—C20—C19−114.6 (2)
C5—C1—C6—C1116.5 (4)C17—Fe1—C20—C16−37.6 (2)
C2—C1—C6—C11−160.7 (3)C3—Fe1—C20—C1647.0 (4)
Fe1—C1—C6—C11108.9 (3)C5—Fe1—C20—C16167.5 (2)
C5—C1—C6—C7−166.6 (3)C2—Fe1—C20—C1683.1 (3)
C2—C1—C6—C716.2 (4)C18—Fe1—C20—C16−81.5 (3)
Fe1—C1—C6—C7−74.2 (4)C4—Fe1—C20—C16−157.5 (7)
C11—C6—C7—C8−0.1 (4)C1—Fe1—C20—C16127.3 (2)
C1—C6—C7—C8−177.1 (3)C19—Fe1—C20—C16−118.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···I10.842.743.575 (3)176
O1—H1B···I1i0.842.783.616 (3)176
C12—H12A···O10.952.393.277 (4)156
C13—H13···I1ii0.953.013.931 (3)163

Symmetry codes: (i) −x, −y+2, −z; (ii) x, −y+3/2, z−1/2.

Table 2 Dihedral angles (°) between the planes.

Note: planes A consists of atoms C1–C5, plane B of atoms C6–C11 and plane C of atoms N1/C12/N2/C13/C14.

PlaneAngle
A and B17.27 (17)
B and C48.81 (17)
A and C32.53 (19)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2694).

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