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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): m517.
Published online 2009 April 10. doi:  10.1107/S1600536809012288
PMCID: PMC2977575

2-Ferrocenyl-3-meth­oxy-6-methyl­pyridine

Abstract

In the title compound, [Fe(C5H5)(C12H12NO)], the dihedral angle between the pyridyl and substituted cyclo­penta­dienyl rings is 23.58 (3)°. The crystal structure is characterized by weak inter­molecular C—H(...)N hydrogen-bonding contacts, leading to the formation of chains running parallel to the n-glide planes. A weak inter­molecular C—H(...)π contact is also present.

Related literature

For historical background and for properties of ferrocenes and derivatives, see: Wang et al. (2008 [triangle]) and references cited therein. For the structure of (Z)-2,3-di(ferrocen­yl)-2-butenedionate, see: Beletskaya et al. (2001 [triangle]). For cyclo­palladated ferrocen­yl–pyrimidine complexes, see: Xu et al. (2009 [triangle]). For the structure of {1-[(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-imino]eth­yl}ferrocene, see: Hao et al. (2008 [triangle]). For the synthesis of functional compounds related to ferrocene-bearing units, see: Sarhan & Izumi (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m517-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C12H12NO)]
  • M r = 307.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m517-efi1.jpg
  • a = 5.9949 (13) Å
  • b = 20.284 (4) Å
  • c = 12.035 (2) Å
  • β = 100.036 (3)°
  • V = 1441.0 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.04 mm−1
  • T = 294 K
  • 0.43 × 0.35 × 0.27 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.663, T max = 0.767
  • 8219 measured reflections
  • 2673 independent reflections
  • 2280 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.076
  • S = 1.06
  • 2673 reflections
  • 183 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL .

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012288/si2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012288/si2164Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of Henan Education Department (No. 2009B150019), the National Science Foundation of China (No. 20872133) and the Innovation Fund for Outstanding Scholars of Henan Province (No. 074200510005).

supplementary crystallographic information

Comment

Since the discovery of ferrocene in the 1950s, the fascinating structural properties of ferrocene and its derivatives have been the subject of increasing interest in all fields of organometallic chemistry (Hao et al., 2008; Xu et al., 2009; Wang et al., 2008 with relevant literature cited therein). Among them, ferrocene-heterocycles are one of the most important ones (Sarhan & Izumi, 2003).

In the title compound (Fig. 1), the dihedral angle between the pyridyl and substituted cyclopentadienyl rings is 23.58 (3)°. The crystal structure is characterised by weak intermolecular C—H···N hydrogen bonding contacts (Table 1), leading to the formation of one-dimensional chains running parallel to the n-glide planes (Fig. 2). Furthermore, a weak intermolecular C—H···π contact may also be considered in the structure (Table 1). Cg1 is the centroid of the Cp ring C8 - C12. The perpendicular distance of H4 to the Cp ring is 2.812 Å. C—H···π contacts were also observed in a triazol-ferrocene derivative (Hao et al., 2008). The n-glide plane symmetry operation is also observed in the structure of 2-Ferrocenyl-6-methylpyridin-3-ol (Wang et al., 2008), in which the nitrogen atoms form classic intermolecular O—H···N hydrogen bonds with the adjacent -OH groups. Both compounds crystallize in the space group P21/n .

Experimental

The title compound was prepared as described in the literature (Beletskaya et al., 2001; Xu et al., 2009) and recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired product as red crystals.

Refinement

H atoms attached to C atoms of the title compound were placed in geometrically idealized positions and treated as riding with C—H distances constrained to 0.93–0.96 Å, and with Uiso(H)=1.2Ueq(C) (1.5Ueq for methyl H).

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
Partial view of the crystal packing showing the formation of the one-dimensional chain structure formed by the weak intermolecular C—H···N hydrogen bonding contacts.

Crystal data

[Fe(C5H5)(C12H12NO)]F(000) = 640
Mr = 307.17Dx = 1.416 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3338 reflections
a = 5.9949 (13) Åθ = 2.7–26.2°
b = 20.284 (4) ŵ = 1.04 mm1
c = 12.035 (2) ÅT = 294 K
β = 100.036 (3)°Block, red
V = 1441.0 (5) Å30.43 × 0.35 × 0.27 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer2673 independent reflections
Radiation source: fine-focus sealed tube2280 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.663, Tmax = 0.767k = −24→23
8219 measured reflectionsl = −14→10

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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0389P)2 + 0.3178P] where P = (Fo2 + 2Fc2)/3
2673 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.27 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
C10.2209 (3)0.19049 (9)0.27110 (15)0.0381 (4)
C20.3488 (4)0.20189 (10)0.37922 (17)0.0454 (5)
C30.2693 (4)0.24755 (11)0.44894 (18)0.0555 (6)
H30.35000.25630.52070.067*
C40.0683 (4)0.27974 (10)0.4098 (2)0.0576 (6)
H40.01370.31080.45520.069*
C5−0.0523 (4)0.26628 (9)0.30382 (18)0.0483 (5)
C6−0.2728 (4)0.29957 (11)0.2575 (2)0.0636 (6)
H6A−0.24990.33050.20020.095*
H6B−0.32770.32240.31720.095*
H6C−0.38180.26710.22550.095*
C70.6707 (4)0.17331 (14)0.5189 (2)0.0729 (7)
H7A0.71170.21870.53330.109*
H7B0.80540.14690.52630.109*
H7C0.57940.15870.57220.109*
C80.2889 (3)0.14341 (9)0.18926 (15)0.0375 (4)
C90.5096 (3)0.11890 (9)0.18035 (17)0.0416 (4)
H90.65210.13030.22980.050*
C100.4844 (4)0.07527 (9)0.08687 (17)0.0461 (5)
H100.60710.05100.06110.055*
C110.2523 (4)0.07186 (10)0.03813 (17)0.0477 (5)
H110.18680.0450−0.02710.057*
C120.1309 (3)0.11391 (9)0.10025 (16)0.0415 (4)
H12−0.03330.12100.08560.050*
C130.0699 (4)−0.01181 (13)0.2693 (2)0.0722 (8)
H13−0.0952−0.00680.25290.087*
C140.1998 (5)−0.05346 (11)0.2134 (2)0.0665 (7)
H140.1411−0.08190.14910.080*
C150.4275 (5)−0.04656 (11)0.2624 (3)0.0683 (7)
H150.5550−0.06960.23860.082*
C160.4429 (5)−0.00088 (13)0.3495 (2)0.0722 (8)
H160.58300.01320.39840.087*
C170.2229 (6)0.02140 (14)0.3562 (2)0.0769 (8)
H170.18200.05300.41090.092*
Fe10.29948 (4)0.042837 (12)0.20323 (2)0.03896 (11)
N10.0252 (3)0.22223 (7)0.23573 (14)0.0416 (4)
O10.5451 (3)0.16693 (8)0.40698 (12)0.0597 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0488 (11)0.0324 (9)0.0342 (10)−0.0068 (8)0.0100 (9)−0.0025 (8)
C20.0538 (12)0.0421 (10)0.0399 (11)−0.0080 (9)0.0073 (9)−0.0020 (9)
C30.0814 (16)0.0475 (12)0.0389 (12)−0.0181 (11)0.0144 (11)−0.0122 (10)
C40.0811 (17)0.0412 (11)0.0560 (14)−0.0047 (11)0.0269 (13)−0.0144 (10)
C50.0627 (13)0.0330 (10)0.0549 (13)−0.0036 (9)0.0255 (11)−0.0037 (9)
C60.0650 (15)0.0465 (13)0.0848 (18)0.0062 (11)0.0283 (13)−0.0044 (12)
C70.0755 (17)0.0905 (19)0.0452 (14)−0.0078 (14)−0.0108 (12)−0.0013 (13)
C80.0477 (10)0.0313 (9)0.0336 (10)0.0011 (7)0.0073 (8)0.0007 (7)
C90.0451 (10)0.0355 (10)0.0449 (12)−0.0024 (8)0.0096 (9)0.0001 (8)
C100.0565 (12)0.0390 (11)0.0456 (12)0.0068 (9)0.0166 (10)−0.0004 (9)
C110.0680 (14)0.0393 (10)0.0330 (11)0.0080 (9)0.0014 (10)−0.0046 (8)
C120.0491 (11)0.0379 (10)0.0345 (10)0.0061 (8)−0.0011 (8)0.0011 (8)
C130.0561 (14)0.0766 (17)0.085 (2)−0.0117 (13)0.0144 (14)0.0298 (15)
C140.0759 (17)0.0432 (12)0.0765 (19)−0.0133 (11)0.0025 (14)0.0082 (12)
C150.0702 (16)0.0464 (13)0.084 (2)0.0045 (11)0.0009 (14)0.0224 (13)
C160.0786 (18)0.0742 (17)0.0542 (16)−0.0149 (14)−0.0153 (13)0.0319 (14)
C170.127 (3)0.0601 (15)0.0502 (15)−0.0075 (16)0.0338 (16)0.0152 (12)
Fe10.04316 (17)0.03381 (16)0.03740 (18)−0.00120 (11)0.00003 (12)0.00266 (11)
N10.0508 (9)0.0325 (8)0.0433 (9)−0.0001 (7)0.0133 (8)−0.0012 (7)
O10.0649 (10)0.0689 (10)0.0398 (9)0.0010 (8)−0.0063 (7)−0.0086 (7)

Geometric parameters (Å, °)

C1—N11.341 (2)C10—C111.415 (3)
C1—C21.410 (3)C10—Fe12.041 (2)
C1—C81.479 (2)C10—H100.9800
C2—O11.364 (3)C11—C121.416 (3)
C2—C31.389 (3)C11—Fe12.044 (2)
C3—C41.379 (3)C11—H110.9800
C3—H30.9300C12—Fe12.0492 (18)
C4—C51.379 (3)C12—H120.9800
C4—H40.9300C13—C141.399 (4)
C5—N11.349 (2)C13—C171.434 (4)
C5—C61.503 (3)C13—Fe12.034 (2)
C6—H6A0.9600C13—H130.9800
C6—H6B0.9600C14—C151.396 (4)
C6—H6C0.9600C14—Fe12.053 (2)
C7—O11.430 (3)C14—H140.9800
C7—H7A0.9600C15—C161.390 (4)
C7—H7B0.9600C15—Fe12.048 (2)
C7—H7C0.9600C15—H150.9800
C8—C121.431 (3)C16—C171.410 (4)
C8—C91.435 (3)C16—Fe12.024 (2)
C8—Fe12.0470 (18)C16—H160.9800
C9—C101.419 (3)C17—Fe12.021 (2)
C9—Fe12.0405 (18)C17—H170.9800
C9—H90.9800
N1—C1—C2121.29 (17)C13—C14—H14125.6
N1—C1—C8115.20 (16)Fe1—C14—H14125.6
C2—C1—C8123.50 (18)C16—C15—C14108.5 (3)
O1—C2—C3124.81 (19)C16—C15—Fe169.12 (13)
O1—C2—C1116.61 (17)C14—C15—Fe170.28 (13)
C3—C2—C1118.6 (2)C16—C15—H15125.8
C4—C3—C2118.7 (2)C14—C15—H15125.8
C4—C3—H3120.6Fe1—C15—H15125.8
C2—C3—H3120.6C15—C16—C17108.5 (2)
C3—C4—C5120.5 (2)C15—C16—Fe170.96 (14)
C3—C4—H4119.7C17—C16—Fe169.50 (13)
C5—C4—H4119.7C15—C16—H16125.8
N1—C5—C4120.8 (2)C17—C16—H16125.8
N1—C5—C6116.5 (2)Fe1—C16—H16125.8
C4—C5—C6122.67 (19)C16—C17—C13107.0 (3)
C5—C6—H6A109.5C16—C17—Fe169.70 (15)
C5—C6—H6B109.5C13—C17—Fe169.76 (14)
H6A—C6—H6B109.5C16—C17—H17126.5
C5—C6—H6C109.5C13—C17—H17126.5
H6A—C6—H6C109.5Fe1—C17—H17126.5
H6B—C6—H6C109.5C17—Fe1—C1640.81 (12)
O1—C7—H7A109.5C17—Fe1—C1341.42 (11)
O1—C7—H7B109.5C16—Fe1—C1368.62 (11)
H7A—C7—H7B109.5C17—Fe1—C10158.66 (12)
O1—C7—H7C109.5C16—Fe1—C10122.60 (10)
H7A—C7—H7C109.5C13—Fe1—C10158.36 (11)
H7B—C7—H7C109.5C17—Fe1—C9121.95 (11)
C12—C8—C9107.31 (16)C16—Fe1—C9105.66 (9)
C12—C8—C1123.04 (17)C13—Fe1—C9160.15 (11)
C9—C8—C1129.64 (17)C10—Fe1—C940.68 (8)
C12—C8—Fe169.63 (10)C17—Fe1—C11158.83 (12)
C9—C8—Fe169.20 (10)C16—Fe1—C11159.61 (11)
C1—C8—Fe1126.65 (13)C13—Fe1—C11123.25 (10)
C10—C9—C8107.66 (17)C10—Fe1—C1140.52 (8)
C10—C9—Fe169.66 (11)C9—Fe1—C1168.61 (8)
C8—C9—Fe169.69 (10)C17—Fe1—C8106.28 (10)
C10—C9—H9126.2C16—Fe1—C8120.70 (10)
C8—C9—H9126.2C13—Fe1—C8124.18 (10)
Fe1—C9—H9126.2C10—Fe1—C868.61 (7)
C11—C10—C9108.69 (17)C9—Fe1—C841.11 (7)
C11—C10—Fe169.88 (12)C11—Fe1—C868.66 (7)
C9—C10—Fe169.66 (11)C17—Fe1—C1567.90 (12)
C11—C10—H10125.7C16—Fe1—C1539.92 (11)
C9—C10—H10125.7C13—Fe1—C1567.65 (11)
Fe1—C10—H10125.7C10—Fe1—C15107.97 (10)
C10—C11—C12108.09 (17)C9—Fe1—C15120.91 (9)
C10—C11—Fe169.60 (11)C11—Fe1—C15124.95 (10)
C12—C11—Fe169.95 (11)C8—Fe1—C15156.28 (9)
C10—C11—H11126.0C17—Fe1—C12122.41 (11)
C12—C11—H11126.0C16—Fe1—C12157.56 (11)
Fe1—C11—H11126.0C13—Fe1—C12108.88 (9)
C11—C12—C8108.25 (17)C10—Fe1—C1268.15 (8)
C11—C12—Fe169.57 (11)C9—Fe1—C1268.74 (8)
C8—C12—Fe169.46 (10)C11—Fe1—C1240.48 (8)
C11—C12—H12125.9C8—Fe1—C1240.91 (7)
C8—C12—H12125.9C15—Fe1—C12161.55 (10)
Fe1—C12—H12125.9C17—Fe1—C1468.07 (12)
C14—C13—C17107.2 (2)C16—Fe1—C1467.38 (10)
C14—C13—Fe170.71 (14)C13—Fe1—C1440.03 (11)
C17—C13—Fe168.82 (14)C10—Fe1—C14123.10 (10)
C14—C13—H13126.4C9—Fe1—C14157.00 (10)
C17—C13—H13126.4C11—Fe1—C14109.84 (10)
Fe1—C13—H13126.4C8—Fe1—C14161.46 (10)
C15—C14—C13108.8 (2)C15—Fe1—C1439.82 (10)
C15—C14—Fe169.90 (13)C12—Fe1—C14125.97 (9)
C13—C14—Fe169.27 (13)C1—N1—C5120.02 (17)
C15—C14—H14125.6C2—O1—C7118.28 (18)
N1—C1—C2—O1179.85 (17)C9—C10—Fe1—C14−158.02 (13)
C8—C1—C2—O10.2 (3)C10—C9—Fe1—C17163.42 (14)
N1—C1—C2—C3−0.7 (3)C8—C9—Fe1—C17−77.75 (16)
C8—C1—C2—C3179.65 (18)C10—C9—Fe1—C16122.15 (15)
O1—C2—C3—C4179.62 (19)C8—C9—Fe1—C16−119.02 (14)
C1—C2—C3—C40.2 (3)C10—C9—Fe1—C13−167.6 (3)
C2—C3—C4—C50.6 (3)C8—C9—Fe1—C13−48.8 (3)
C3—C4—C5—N1−1.0 (3)C8—C9—Fe1—C10118.83 (16)
C3—C4—C5—C6179.5 (2)C10—C9—Fe1—C11−37.19 (12)
N1—C1—C8—C12−23.2 (3)C8—C9—Fe1—C1181.64 (12)
C2—C1—C8—C12156.51 (18)C10—C9—Fe1—C8−118.83 (16)
N1—C1—C8—C9156.33 (18)C10—C9—Fe1—C1581.66 (16)
C2—C1—C8—C9−24.0 (3)C8—C9—Fe1—C15−159.51 (13)
N1—C1—C8—Fe1−111.27 (17)C10—C9—Fe1—C12−80.79 (13)
C2—C1—C8—Fe168.4 (2)C8—C9—Fe1—C1238.04 (11)
C12—C8—C9—C100.1 (2)C10—C9—Fe1—C1453.4 (3)
C1—C8—C9—C10−179.48 (18)C8—C9—Fe1—C14172.2 (2)
Fe1—C8—C9—C1059.55 (13)C10—C11—Fe1—C17161.5 (3)
C12—C8—C9—Fe1−59.44 (13)C12—C11—Fe1—C1742.3 (3)
C1—C8—C9—Fe1121.0 (2)C10—C11—Fe1—C16−39.8 (3)
C8—C9—C10—C11−0.4 (2)C12—C11—Fe1—C16−159.1 (2)
Fe1—C9—C10—C1159.16 (14)C10—C11—Fe1—C13−160.67 (14)
C8—C9—C10—Fe1−59.57 (13)C12—C11—Fe1—C1380.10 (16)
C9—C10—C11—C120.6 (2)C12—C11—Fe1—C10−119.24 (17)
Fe1—C10—C11—C1259.58 (14)C10—C11—Fe1—C937.33 (11)
C9—C10—C11—Fe1−59.02 (14)C12—C11—Fe1—C9−81.91 (12)
C10—C11—C12—C8−0.5 (2)C10—C11—Fe1—C881.62 (12)
Fe1—C11—C12—C858.87 (13)C12—C11—Fe1—C8−37.61 (11)
C10—C11—C12—Fe1−59.36 (14)C10—C11—Fe1—C15−76.21 (15)
C9—C8—C12—C110.2 (2)C12—C11—Fe1—C15164.55 (13)
C1—C8—C12—C11179.86 (17)C10—C11—Fe1—C12119.24 (17)
Fe1—C8—C12—C11−58.94 (13)C10—C11—Fe1—C14−118.13 (13)
C9—C8—C12—Fe159.17 (13)C12—C11—Fe1—C14122.63 (14)
C1—C8—C12—Fe1−121.20 (17)C12—C8—Fe1—C17−121.03 (15)
C17—C13—C14—C15−0.5 (3)C9—C8—Fe1—C17120.25 (15)
Fe1—C13—C14—C1558.89 (17)C1—C8—Fe1—C17−4.4 (2)
C17—C13—C14—Fe1−59.40 (16)C12—C8—Fe1—C16−162.99 (14)
C13—C14—C15—C160.2 (3)C9—C8—Fe1—C1678.29 (15)
Fe1—C14—C15—C1658.73 (16)C1—C8—Fe1—C16−46.3 (2)
C13—C14—C15—Fe1−58.50 (17)C12—C8—Fe1—C13−79.27 (15)
C14—C15—C16—C170.2 (3)C9—C8—Fe1—C13162.01 (13)
Fe1—C15—C16—C1759.60 (16)C1—C8—Fe1—C1337.4 (2)
C14—C15—C16—Fe1−59.44 (17)C12—C8—Fe1—C1080.89 (13)
C15—C16—C17—C13−0.5 (3)C9—C8—Fe1—C10−37.83 (12)
Fe1—C16—C17—C1360.05 (17)C1—C8—Fe1—C10−162.45 (18)
C15—C16—C17—Fe1−60.51 (17)C12—C8—Fe1—C9118.72 (16)
C14—C13—C17—C160.6 (3)C1—C8—Fe1—C9−124.6 (2)
Fe1—C13—C17—C16−60.01 (16)C12—C8—Fe1—C1137.23 (12)
C14—C13—C17—Fe160.60 (17)C9—C8—Fe1—C11−81.49 (12)
C13—C17—Fe1—C16−118.0 (2)C1—C8—Fe1—C11153.89 (19)
C16—C17—Fe1—C13118.0 (2)C12—C8—Fe1—C15167.0 (2)
C16—C17—Fe1—C10−45.6 (3)C9—C8—Fe1—C1548.3 (3)
C13—C17—Fe1—C10−163.6 (2)C1—C8—Fe1—C15−76.3 (3)
C16—C17—Fe1—C9−76.37 (18)C9—C8—Fe1—C12−118.72 (16)
C13—C17—Fe1—C9165.62 (15)C1—C8—Fe1—C12116.7 (2)
C16—C17—Fe1—C11168.8 (2)C12—C8—Fe1—C14−51.7 (3)
C13—C17—Fe1—C1150.8 (3)C9—C8—Fe1—C14−170.4 (3)
C16—C17—Fe1—C8−118.39 (16)C1—C8—Fe1—C1465.0 (4)
C13—C17—Fe1—C8123.61 (16)C16—C15—Fe1—C17−38.02 (17)
C16—C17—Fe1—C1537.22 (16)C14—C15—Fe1—C1781.80 (19)
C13—C17—Fe1—C15−80.78 (17)C14—C15—Fe1—C16119.8 (3)
C16—C17—Fe1—C12−160.05 (15)C16—C15—Fe1—C13−82.94 (19)
C13—C17—Fe1—C1281.95 (18)C14—C15—Fe1—C1336.89 (18)
C16—C17—Fe1—C1480.32 (18)C16—C15—Fe1—C10119.66 (17)
C13—C17—Fe1—C14−37.68 (16)C14—C15—Fe1—C10−120.51 (17)
C15—C16—Fe1—C17119.2 (2)C16—C15—Fe1—C976.98 (19)
C15—C16—Fe1—C1380.30 (18)C14—C15—Fe1—C9−163.20 (16)
C17—C16—Fe1—C13−38.85 (17)C16—C15—Fe1—C11161.22 (16)
C15—C16—Fe1—C10−78.84 (18)C14—C15—Fe1—C11−78.9 (2)
C17—C16—Fe1—C10162.01 (15)C16—C15—Fe1—C842.1 (3)
C15—C16—Fe1—C9−119.76 (16)C14—C15—Fe1—C8161.9 (2)
C17—C16—Fe1—C9121.09 (16)C16—C15—Fe1—C12−165.7 (3)
C15—C16—Fe1—C11−49.2 (3)C14—C15—Fe1—C12−45.8 (4)
C17—C16—Fe1—C11−168.4 (2)C16—C15—Fe1—C14−119.8 (3)
C15—C16—Fe1—C8−161.72 (15)C11—C12—Fe1—C17−163.27 (15)
C17—C16—Fe1—C879.13 (18)C8—C12—Fe1—C1776.97 (16)
C17—C16—Fe1—C15−119.2 (2)C11—C12—Fe1—C16161.0 (2)
C15—C16—Fe1—C12168.2 (2)C8—C12—Fe1—C1641.2 (3)
C17—C16—Fe1—C1249.0 (3)C11—C12—Fe1—C13−119.46 (15)
C15—C16—Fe1—C1437.00 (17)C8—C12—Fe1—C13120.79 (14)
C17—C16—Fe1—C14−82.15 (18)C11—C12—Fe1—C1037.65 (12)
C14—C13—Fe1—C17−118.2 (2)C8—C12—Fe1—C10−82.10 (12)
C14—C13—Fe1—C16−79.86 (17)C11—C12—Fe1—C981.54 (13)
C17—C13—Fe1—C1638.29 (17)C8—C12—Fe1—C9−38.22 (11)
C14—C13—Fe1—C1045.7 (3)C8—C12—Fe1—C11−119.76 (17)
C17—C13—Fe1—C10163.9 (2)C11—C12—Fe1—C8119.76 (17)
C14—C13—Fe1—C9−156.5 (2)C11—C12—Fe1—C15−43.6 (4)
C17—C13—Fe1—C9−38.4 (3)C8—C12—Fe1—C15−163.4 (3)
C14—C13—Fe1—C1181.39 (17)C11—C12—Fe1—C14−78.20 (17)
C17—C13—Fe1—C11−160.45 (16)C8—C12—Fe1—C14162.04 (13)
C14—C13—Fe1—C8166.76 (14)C15—C14—Fe1—C17−81.35 (19)
C17—C13—Fe1—C8−75.09 (18)C13—C14—Fe1—C1738.96 (17)
C14—C13—Fe1—C15−36.71 (16)C15—C14—Fe1—C16−37.10 (18)
C17—C13—Fe1—C1581.45 (18)C13—C14—Fe1—C1683.22 (18)
C14—C13—Fe1—C12123.92 (15)C15—C14—Fe1—C13−120.3 (2)
C17—C13—Fe1—C12−117.93 (17)C15—C14—Fe1—C1078.06 (19)
C17—C13—Fe1—C14118.2 (2)C13—C14—Fe1—C10−161.63 (15)
C11—C10—Fe1—C17−161.7 (3)C15—C14—Fe1—C939.4 (3)
C9—C10—Fe1—C17−41.7 (3)C13—C14—Fe1—C9159.7 (2)
C11—C10—Fe1—C16164.63 (13)C15—C14—Fe1—C11121.21 (17)
C9—C10—Fe1—C16−75.38 (16)C13—C14—Fe1—C11−118.47 (16)
C11—C10—Fe1—C1348.7 (3)C15—C14—Fe1—C8−156.9 (3)
C9—C10—Fe1—C13168.6 (2)C13—C14—Fe1—C8−36.6 (4)
C11—C10—Fe1—C9−119.99 (16)C13—C14—Fe1—C15120.3 (2)
C9—C10—Fe1—C11119.99 (16)C15—C14—Fe1—C12163.71 (16)
C11—C10—Fe1—C8−81.77 (12)C13—C14—Fe1—C12−75.98 (18)
C9—C10—Fe1—C838.22 (11)C2—C1—N1—C50.3 (3)
C11—C10—Fe1—C15123.19 (13)C8—C1—N1—C5−179.98 (16)
C9—C10—Fe1—C15−116.83 (13)C4—C5—N1—C10.5 (3)
C11—C10—Fe1—C12−37.61 (11)C6—C5—N1—C1180.00 (17)
C9—C10—Fe1—C1282.37 (12)C3—C2—O1—C75.3 (3)
C11—C10—Fe1—C1481.99 (15)C1—C2—O1—C7−175.28 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···N1i0.932.653.577 (3)172
C4—H4···Cg1ii0.932.963.880 (3)173

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2164).

References

  • Beletskaya, I. P., Tsvetkov, A. V., Latyshev, G. V., Tafeenko, V. A. & Lukashev, N. V. (2001). J. Organomet. Chem.637–639, 653-663.
  • Bruker (2004). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hao, X.-Q., Liang, D.-S., Liu, R.-Y., Gong, J.-F. & Song, M.-P. (2008). Acta Cryst. E64, m1275. [PMC free article] [PubMed]
  • Sarhan, A. A. O. & Izumi, T. (2003). J. Organomet. Chem.675, 1–12.
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Z.-Q., Xu, C., Cen, F.-F., Li, Y.-F. & Ji, B.-M. (2008). Acta Cryst. E64, m1633. [PMC free article] [PubMed]
  • Xu, C., Wang, Z. Q., Fu, W. J., Lou, X. H., Li, Y. F., Cen, F. F., Ma, H. J. & Ji, B. M. (2009). Organometallics, 28, 1909–1916.

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