PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1633.
Published online 2008 November 29. doi:  10.1107/S1600536808039597
PMCID: PMC2960045

2-Ferrocenyl-6-methyl­pyridin-3-ol

Abstract

In the title compound, [Fe(C5H5)(C11H10NO)], the dihedral angle between the pyridyl and substituted cyclo­penta­dienyl rings is 20.4 (3)°. The H atoms of the methyl group are disordered over two positions; their site-occupation factors were fixed at 0.5. The crystal structure is stabilized by well defined inter­molecular O—H(...)N and C—H(...)O hydrogen bonds, leading to the formation of a two-dimensional network parallel to (101).

Related literature

For ferrocene and its derivatives, see: Beletskaya et al. (2001 [triangle]); Hayashi & Togni (1995 [triangle]); Kealy & Pauson (1951 [triangle]); Sarhan & Izumi (2003 [triangle]); Staveren & Metzler-Nolte (2004 [triangle]); Xu et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1633-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C11H10NO)]
  • M r = 293.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1633-efi1.jpg
  • a = 10.4370 (13) Å
  • b = 12.7196 (15) Å
  • c = 10.5424 (13) Å
  • β = 111.0330 (10)°
  • V = 1306.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.14 mm−1
  • T = 291 (2) K
  • 0.37 × 0.23 × 0.21 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.675, T max = 0.793
  • 7569 measured reflections
  • 2422 independent reflections
  • 1970 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.099
  • S = 1.08
  • 2422 reflections
  • 173 parameters
  • H-atom parameters constrained
  • Δρmax = 0.63 e Å−3
  • Δρmin = −0.54 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/S1600536808039597/fj2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039597/fj2173Isup2.hkl

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

Acknowledgments

This work was supported by the Doctoral Foundation of Luoyang Normal University.

supplementary crystallographic information

Comment

Since the discovery of ferrocene in the 1950's (Kealy & Pauson, 1951), the fascinating structural properties of ferrocene and its derivatives have been the subject of increasing interest in all fields of organometallic chemistry (Hayashi et al., 1995; Staveren et al., 2004; Xu et al., 2007). Among them, ferrocene-heterocycles are one of the most important ones (Sarhan & Izumi, 2003). Herein we report the crystal structure of the title compound.

A view of the molecular structure of the title compound is given in Fig.1. The hydrogen atoms of methyl groups are disordered; site-occupation factors were fixed at 0.5. The pyridyl and Cp ring form a dihedral angle of 20.4 (3)°. In the crystal of the title compound, intermolecular O—H···N and C—H···O hydrogen bonds are present(Table 1), resulting in a two-dimensional supramolecular architecture(Fig.2).

Experimental

The title compound was prepared as described in literature (Beletskaya et al., 2001) and recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired product as red crystals suitable for single-crystal X-ray diffraction.

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 Uĩso~(H)=1.2Ueq(C)(1.5Ueq for methyl H).

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids at the 30% probability level. Only one disordered component of the methyl group is shown.
Fig. 2.
Partial view of the crystal packing showing the intermolecular O—H···N and C—H···O hydrogen bonds. One disordered component of the methyl group has been omitted for clarity.

Crystal data

[Fe(C5H5)(C11H10NO)]F000 = 608
Mr = 293.14Dx = 1.491 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2766 reflections
a = 10.4370 (13) Åθ = 2.4–25.0º
b = 12.7196 (15) ŵ = 1.14 mm1
c = 10.5424 (13) ÅT = 291 (2) K
β = 111.0330 (10)ºBlock, red
V = 1306.3 (3) Å30.37 × 0.23 × 0.21 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer2422 independent reflections
Radiation source: fine-focus sealed tube1970 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 291(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −10→12
Tmin = 0.675, Tmax = 0.794k = −15→15
7569 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.099  w = 1/[σ2(Fo2) + (0.046P)2 + 0.7167P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
2422 reflectionsΔρmax = 0.63 e Å3
173 parametersΔρmin = −0.54 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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*/UeqOcc. (<1)
Fe10.35569 (4)1.02041 (3)0.20685 (4)0.04595 (16)
O10.5672 (2)0.78281 (18)0.36235 (18)0.0576 (5)
H10.64890.76880.39930.086*
N10.3444 (2)0.74252 (16)0.0124 (2)0.0424 (5)
C10.3813 (5)1.1764 (3)0.1792 (5)0.0962 (14)
H1A0.30751.22830.14540.115*
C20.4350 (5)1.1151 (3)0.0982 (4)0.0905 (13)
H20.40571.1177−0.00110.109*
C30.5377 (4)1.0523 (3)0.1836 (4)0.0788 (11)
H30.59321.00190.15520.095*
C40.5481 (4)1.0718 (3)0.3185 (4)0.0827 (11)
H40.61251.03860.40040.099*
C50.4490 (4)1.1502 (3)0.3136 (4)0.0856 (12)
H50.43251.18060.39180.103*
C60.3115 (3)0.8626 (2)0.1744 (3)0.0452 (6)
C70.3146 (3)0.8949 (3)0.3049 (3)0.0573 (7)
H70.37540.86660.39220.069*
C80.2150 (3)0.9752 (3)0.2872 (4)0.0693 (9)
H80.19481.01140.36000.083*
C90.1511 (3)0.9943 (3)0.1476 (4)0.0778 (11)
H90.07871.04620.10610.093*
C100.2095 (3)0.9257 (3)0.0766 (3)0.0638 (9)
H100.18490.9227−0.02220.077*
C110.3946 (2)0.78116 (19)0.1409 (2)0.0389 (6)
C120.5209 (3)0.7445 (2)0.2335 (2)0.0419 (6)
C130.5943 (3)0.6722 (2)0.1894 (3)0.0487 (7)
H130.67800.64720.24900.058*
C140.5436 (3)0.6372 (2)0.0573 (3)0.0489 (6)
H140.59360.58960.02640.059*
C150.4175 (3)0.6734 (2)−0.0295 (3)0.0455 (6)
C160.3599 (3)0.6378 (3)−0.1758 (3)0.0637 (8)
H16A0.27240.6705−0.22070.096*0.50
H16B0.34900.5628−0.17900.096*0.50
H16C0.42170.6574−0.22060.096*0.50
H16D0.42300.5900−0.19290.096*0.50
H16E0.34640.6977−0.23450.096*0.50
H16F0.27370.6030−0.19290.096*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0494 (3)0.0480 (3)0.0396 (2)0.00711 (17)0.01483 (18)−0.00218 (16)
O10.0420 (11)0.0758 (14)0.0404 (10)0.0147 (10)−0.0031 (8)−0.0069 (9)
N10.0351 (11)0.0414 (12)0.0407 (11)−0.0034 (9)0.0014 (9)0.0023 (9)
C10.143 (4)0.044 (2)0.120 (4)0.011 (2)0.070 (3)−0.003 (2)
C20.150 (4)0.059 (2)0.088 (3)−0.012 (2)0.074 (3)−0.002 (2)
C30.080 (3)0.067 (2)0.110 (3)−0.024 (2)0.058 (2)−0.031 (2)
C40.063 (2)0.089 (3)0.092 (3)−0.021 (2)0.022 (2)−0.033 (2)
C50.102 (3)0.076 (2)0.091 (3)−0.020 (2)0.050 (2)−0.039 (2)
C60.0298 (13)0.0498 (16)0.0499 (15)−0.0026 (11)0.0069 (11)0.0015 (12)
C70.0532 (18)0.068 (2)0.0575 (17)0.0024 (15)0.0282 (14)0.0088 (14)
C80.0517 (19)0.085 (2)0.084 (2)0.0068 (17)0.0393 (19)−0.0064 (18)
C90.0382 (17)0.090 (3)0.089 (3)0.0194 (17)0.0033 (18)−0.013 (2)
C100.0414 (16)0.071 (2)0.0606 (18)0.0121 (15)−0.0037 (14)−0.0132 (16)
C110.0315 (13)0.0380 (13)0.0413 (13)−0.0045 (10)0.0060 (11)0.0036 (10)
C120.0370 (14)0.0419 (14)0.0375 (13)−0.0012 (11)0.0019 (11)0.0020 (10)
C130.0405 (15)0.0439 (15)0.0489 (15)0.0084 (12)0.0003 (12)0.0034 (12)
C140.0488 (16)0.0385 (14)0.0525 (15)0.0045 (12)0.0097 (13)−0.0019 (11)
C150.0464 (16)0.0372 (14)0.0450 (14)−0.0056 (12)0.0067 (12)−0.0005 (11)
C160.063 (2)0.0625 (19)0.0502 (17)0.0023 (16)0.0019 (15)−0.0102 (14)

Geometric parameters (Å, °)

Fe1—C82.024 (3)C6—C71.426 (4)
Fe1—C92.025 (3)C6—C101.433 (4)
Fe1—C72.029 (3)C6—C111.473 (4)
Fe1—C22.032 (4)C7—C81.421 (4)
Fe1—C42.036 (3)C7—H70.9800
Fe1—C12.036 (4)C8—C91.401 (5)
Fe1—C52.038 (4)C8—H80.9800
Fe1—C102.040 (3)C9—C101.421 (5)
Fe1—C32.041 (4)C9—H90.9800
Fe1—C62.061 (3)C10—H100.9800
O1—C121.358 (3)C11—C121.408 (3)
O1—H10.8200C12—C131.381 (4)
N1—C151.339 (3)C13—C141.374 (4)
N1—C111.357 (3)C13—H130.9300
C1—C51.377 (6)C14—C151.385 (4)
C1—C21.412 (5)C14—H140.9300
C1—H1A0.9800C15—C161.509 (4)
C2—C31.381 (6)C16—H16A0.9600
C2—H20.9800C16—H16B0.9600
C3—C41.408 (5)C16—H16C0.9600
C3—H30.9800C16—H16D0.9600
C4—C51.425 (6)C16—H16E0.9600
C4—H40.9800C16—H16F0.9600
C5—H50.9800
C8—Fe1—C940.49 (16)C1—C5—Fe170.2 (2)
C8—Fe1—C741.06 (13)C4—C5—Fe169.5 (2)
C9—Fe1—C768.66 (15)C1—C5—H5126.2
C8—Fe1—C2155.18 (17)C4—C5—H5126.2
C9—Fe1—C2121.4 (2)Fe1—C5—H5126.2
C7—Fe1—C2163.08 (15)C7—C6—C10106.6 (3)
C8—Fe1—C4124.23 (16)C7—C6—C11128.5 (2)
C9—Fe1—C4160.47 (16)C10—C6—C11124.9 (3)
C7—Fe1—C4107.62 (16)C7—C6—Fe168.41 (17)
C2—Fe1—C467.60 (19)C10—C6—Fe168.77 (17)
C8—Fe1—C1119.26 (17)C11—C6—Fe1127.50 (18)
C9—Fe1—C1107.08 (18)C8—C7—C6108.5 (3)
C7—Fe1—C1154.37 (15)C8—C7—Fe169.29 (19)
C2—Fe1—C140.61 (16)C6—C7—Fe170.80 (16)
C4—Fe1—C167.5 (2)C8—C7—H7125.7
C8—Fe1—C5105.90 (16)C6—C7—H7125.7
C9—Fe1—C5123.03 (16)Fe1—C7—H7125.7
C7—Fe1—C5120.16 (16)C9—C8—C7108.2 (3)
C2—Fe1—C567.68 (17)C9—C8—Fe169.8 (2)
C4—Fe1—C540.93 (16)C7—C8—Fe169.66 (17)
C1—Fe1—C539.52 (16)C9—C8—H8125.9
C8—Fe1—C1068.53 (15)C7—C8—H8125.9
C9—Fe1—C1040.92 (14)Fe1—C8—H8125.9
C7—Fe1—C1068.58 (14)C8—C9—C10108.3 (3)
C2—Fe1—C10109.16 (17)C8—C9—Fe169.71 (19)
C4—Fe1—C10157.32 (14)C10—C9—Fe170.09 (18)
C1—Fe1—C10125.72 (18)C8—C9—H9125.8
C5—Fe1—C10160.69 (16)C10—C9—H9125.8
C8—Fe1—C3162.32 (18)Fe1—C9—H9125.8
C9—Fe1—C3156.78 (18)C9—C10—C6108.3 (3)
C7—Fe1—C3126.37 (16)C9—C10—Fe168.99 (19)
C2—Fe1—C339.63 (17)C6—C10—Fe170.33 (16)
C4—Fe1—C340.41 (15)C9—C10—H10125.9
C1—Fe1—C367.29 (18)C6—C10—H10125.9
C5—Fe1—C367.95 (15)Fe1—C10—H10125.9
C10—Fe1—C3122.69 (14)N1—C11—C12120.2 (2)
C8—Fe1—C668.91 (13)N1—C11—C6116.3 (2)
C9—Fe1—C668.94 (13)C12—C11—C6123.5 (2)
C7—Fe1—C640.79 (11)O1—C12—C13122.3 (2)
C2—Fe1—C6126.58 (13)O1—C12—C11118.9 (2)
C4—Fe1—C6121.60 (15)C13—C12—C11118.8 (2)
C1—Fe1—C6163.36 (16)C14—C13—C12119.9 (2)
C5—Fe1—C6156.22 (16)C14—C13—H13120.0
C10—Fe1—C640.90 (11)C12—C13—H13120.0
C3—Fe1—C6109.62 (13)C13—C14—C15119.4 (3)
C12—O1—H1109.5C13—C14—H14120.3
C15—N1—C11120.4 (2)C15—C14—H14120.3
C5—C1—C2108.7 (4)N1—C15—C14121.3 (2)
C5—C1—Fe170.3 (2)N1—C15—C16118.0 (2)
C2—C1—Fe169.5 (2)C14—C15—C16120.7 (3)
C5—C1—H1A125.7C15—C16—H16A109.5
C2—C1—H1A125.7C15—C16—H16B109.5
Fe1—C1—H1A125.7H16A—C16—H16B109.5
C3—C2—C1108.0 (4)C15—C16—H16C109.5
C3—C2—Fe170.5 (2)H16A—C16—H16C109.5
C1—C2—Fe169.9 (2)H16B—C16—H16C109.5
C3—C2—H2126.0C15—C16—H16D109.5
C1—C2—H2126.0H16A—C16—H16D141.1
Fe1—C2—H2126.0H16B—C16—H16D56.3
C2—C3—C4108.5 (4)H16C—C16—H16D56.3
C2—C3—Fe169.8 (2)C15—C16—H16E109.5
C4—C3—Fe169.6 (2)H16A—C16—H16E56.3
C2—C3—H3125.8H16B—C16—H16E141.1
C4—C3—H3125.8H16C—C16—H16E56.3
Fe1—C3—H3125.8H16D—C16—H16E109.5
C3—C4—C5107.2 (4)C15—C16—H16F109.5
C3—C4—Fe170.0 (2)H16A—C16—H16F56.3
C5—C4—Fe169.6 (2)H16B—C16—H16F56.3
C3—C4—H4126.4H16C—C16—H16F141.1
C5—C4—H4126.4H16D—C16—H16F109.5
Fe1—C4—H4126.4H16E—C16—H16F109.5
C1—C5—C4107.7 (3)
C8—Fe1—C1—C579.3 (3)C8—Fe1—C6—C11−160.5 (3)
C9—Fe1—C1—C5121.6 (3)C9—Fe1—C6—C11155.9 (3)
C7—Fe1—C1—C545.4 (5)C7—Fe1—C6—C11−122.7 (3)
C2—Fe1—C1—C5−119.8 (4)C2—Fe1—C6—C1141.8 (3)
C4—Fe1—C1—C5−38.5 (2)C4—Fe1—C6—C11−42.4 (3)
C10—Fe1—C1—C5162.7 (2)C1—Fe1—C6—C1176.9 (6)
C3—Fe1—C1—C5−82.4 (3)C5—Fe1—C6—C11−79.0 (4)
C6—Fe1—C1—C5−165.0 (4)C10—Fe1—C6—C11118.3 (3)
C8—Fe1—C1—C2−160.9 (3)C3—Fe1—C6—C110.7 (3)
C9—Fe1—C1—C2−118.6 (3)C10—C6—C7—C80.8 (3)
C7—Fe1—C1—C2165.3 (3)C11—C6—C7—C8−179.3 (3)
C4—Fe1—C1—C281.3 (3)Fe1—C6—C7—C859.2 (2)
C5—Fe1—C1—C2119.8 (4)C10—C6—C7—Fe1−58.4 (2)
C10—Fe1—C1—C2−77.4 (3)C11—C6—C7—Fe1121.5 (3)
C3—Fe1—C1—C237.4 (3)C9—Fe1—C7—C8−37.4 (2)
C6—Fe1—C1—C2−45.2 (7)C2—Fe1—C7—C8−167.0 (5)
C5—C1—C2—C3−0.9 (5)C4—Fe1—C7—C8122.3 (2)
Fe1—C1—C2—C3−60.5 (3)C1—Fe1—C7—C847.7 (5)
C5—C1—C2—Fe159.6 (3)C5—Fe1—C7—C879.3 (3)
C8—Fe1—C2—C3161.4 (3)C10—Fe1—C7—C8−81.5 (2)
C9—Fe1—C2—C3−162.0 (2)C3—Fe1—C7—C8163.0 (2)
C7—Fe1—C2—C3−39.2 (6)C6—Fe1—C7—C8−119.5 (3)
C4—Fe1—C2—C337.5 (2)C8—Fe1—C7—C6119.5 (3)
C1—Fe1—C2—C3118.6 (4)C9—Fe1—C7—C682.08 (19)
C5—Fe1—C2—C381.9 (3)C2—Fe1—C7—C6−47.5 (6)
C10—Fe1—C2—C3−118.5 (2)C4—Fe1—C7—C6−118.27 (18)
C6—Fe1—C2—C3−76.1 (3)C1—Fe1—C7—C6167.2 (4)
C8—Fe1—C2—C142.8 (5)C5—Fe1—C7—C6−161.19 (19)
C9—Fe1—C2—C179.4 (3)C10—Fe1—C7—C637.99 (17)
C7—Fe1—C2—C1−157.8 (5)C3—Fe1—C7—C6−77.6 (2)
C4—Fe1—C2—C1−81.1 (3)C6—C7—C8—C9−0.8 (4)
C5—Fe1—C2—C1−36.6 (3)Fe1—C7—C8—C959.4 (3)
C10—Fe1—C2—C1123.0 (3)C6—C7—C8—Fe1−60.1 (2)
C3—Fe1—C2—C1−118.6 (4)C7—Fe1—C8—C9−119.4 (3)
C6—Fe1—C2—C1165.4 (3)C2—Fe1—C8—C951.6 (5)
C1—C2—C3—C41.0 (5)C4—Fe1—C8—C9163.5 (2)
Fe1—C2—C3—C4−59.1 (3)C1—Fe1—C8—C982.1 (3)
C1—C2—C3—Fe160.1 (3)C5—Fe1—C8—C9122.6 (2)
C8—Fe1—C3—C2−153.9 (4)C10—Fe1—C8—C9−37.8 (2)
C9—Fe1—C3—C242.0 (5)C3—Fe1—C8—C9−170.4 (4)
C7—Fe1—C3—C2166.8 (2)C6—Fe1—C8—C9−81.9 (2)
C4—Fe1—C3—C2−119.8 (3)C9—Fe1—C8—C7119.4 (3)
C1—Fe1—C3—C2−38.3 (2)C2—Fe1—C8—C7171.0 (3)
C5—Fe1—C3—C2−81.2 (3)C4—Fe1—C8—C7−77.1 (3)
C10—Fe1—C3—C280.6 (3)C1—Fe1—C8—C7−158.5 (2)
C6—Fe1—C3—C2124.2 (2)C5—Fe1—C8—C7−117.9 (2)
C8—Fe1—C3—C4−34.1 (6)C10—Fe1—C8—C781.6 (2)
C9—Fe1—C3—C4161.8 (4)C3—Fe1—C8—C7−51.0 (6)
C7—Fe1—C3—C4−73.4 (3)C6—Fe1—C8—C737.56 (19)
C2—Fe1—C3—C4119.8 (3)C7—C8—C9—C100.4 (4)
C1—Fe1—C3—C481.5 (3)Fe1—C8—C9—C1059.7 (3)
C5—Fe1—C3—C438.6 (3)C7—C8—C9—Fe1−59.3 (2)
C10—Fe1—C3—C4−159.6 (2)C7—Fe1—C9—C837.9 (2)
C6—Fe1—C3—C4−116.1 (2)C2—Fe1—C9—C8−157.3 (2)
C2—C3—C4—C5−0.7 (4)C4—Fe1—C9—C8−44.7 (6)
Fe1—C3—C4—C5−59.9 (3)C1—Fe1—C9—C8−115.3 (2)
C2—C3—C4—Fe159.2 (3)C5—Fe1—C9—C8−75.0 (3)
C8—Fe1—C4—C3168.1 (2)C10—Fe1—C9—C8119.4 (3)
C9—Fe1—C4—C3−158.4 (5)C3—Fe1—C9—C8172.7 (3)
C7—Fe1—C4—C3125.9 (3)C6—Fe1—C9—C881.8 (2)
C2—Fe1—C4—C3−36.8 (2)C8—Fe1—C9—C10−119.4 (3)
C1—Fe1—C4—C3−80.9 (3)C7—Fe1—C9—C10−81.5 (2)
C5—Fe1—C4—C3−118.1 (4)C2—Fe1—C9—C1083.3 (3)
C10—Fe1—C4—C349.4 (5)C4—Fe1—C9—C10−164.1 (5)
C6—Fe1—C4—C383.4 (3)C1—Fe1—C9—C10125.3 (2)
C8—Fe1—C4—C5−73.8 (3)C5—Fe1—C9—C10165.6 (2)
C9—Fe1—C4—C5−40.3 (6)C3—Fe1—C9—C1053.3 (5)
C7—Fe1—C4—C5−116.0 (3)C6—Fe1—C9—C10−37.6 (2)
C2—Fe1—C4—C581.3 (3)C8—C9—C10—C60.1 (4)
C1—Fe1—C4—C537.2 (2)Fe1—C9—C10—C659.6 (2)
C10—Fe1—C4—C5167.5 (4)C8—C9—C10—Fe1−59.4 (3)
C3—Fe1—C4—C5118.1 (4)C7—C6—C10—C9−0.6 (4)
C6—Fe1—C4—C5−158.5 (2)C11—C6—C10—C9179.6 (3)
C2—C1—C5—C40.5 (5)Fe1—C6—C10—C9−58.7 (2)
Fe1—C1—C5—C459.6 (3)C7—C6—C10—Fe158.1 (2)
C2—C1—C5—Fe1−59.1 (3)C11—C6—C10—Fe1−121.7 (3)
C3—C4—C5—C10.2 (5)C8—Fe1—C10—C937.4 (2)
Fe1—C4—C5—C1−60.0 (3)C7—Fe1—C10—C981.7 (2)
C3—C4—C5—Fe160.2 (2)C2—Fe1—C10—C9−116.2 (3)
C8—Fe1—C5—C1−117.0 (3)C4—Fe1—C10—C9166.2 (4)
C9—Fe1—C5—C1−76.2 (3)C1—Fe1—C10—C9−73.9 (3)
C7—Fe1—C5—C1−159.1 (2)C5—Fe1—C10—C9−39.1 (6)
C2—Fe1—C5—C137.6 (3)C3—Fe1—C10—C9−157.9 (3)
C4—Fe1—C5—C1118.7 (4)C6—Fe1—C10—C9119.6 (3)
C10—Fe1—C5—C1−46.7 (6)C8—Fe1—C10—C6−82.2 (2)
C3—Fe1—C5—C180.6 (3)C9—Fe1—C10—C6−119.6 (3)
C6—Fe1—C5—C1169.4 (3)C7—Fe1—C10—C6−37.89 (17)
C8—Fe1—C5—C4124.4 (3)C2—Fe1—C10—C6124.2 (2)
C9—Fe1—C5—C4165.1 (2)C4—Fe1—C10—C646.6 (5)
C7—Fe1—C5—C482.2 (3)C1—Fe1—C10—C6166.5 (2)
C2—Fe1—C5—C4−81.1 (3)C5—Fe1—C10—C6−158.7 (4)
C1—Fe1—C5—C4−118.7 (4)C3—Fe1—C10—C682.4 (2)
C10—Fe1—C5—C4−165.4 (4)C15—N1—C11—C12−3.4 (4)
C3—Fe1—C5—C4−38.1 (3)C15—N1—C11—C6175.6 (2)
C6—Fe1—C5—C450.7 (4)C7—C6—C11—N1160.0 (3)
C8—Fe1—C6—C7−37.80 (19)C10—C6—C11—N1−20.3 (4)
C9—Fe1—C6—C7−81.3 (2)Fe1—C6—C11—N1−109.0 (2)
C2—Fe1—C6—C7164.5 (2)C7—C6—C11—C12−21.1 (4)
C4—Fe1—C6—C780.3 (2)C10—C6—C11—C12158.7 (3)
C1—Fe1—C6—C7−160.4 (5)Fe1—C6—C11—C1270.0 (3)
C5—Fe1—C6—C743.7 (4)N1—C11—C12—O1−178.5 (2)
C10—Fe1—C6—C7−118.9 (3)C6—C11—C12—O12.5 (4)
C3—Fe1—C6—C7123.4 (2)N1—C11—C12—C132.5 (4)
C8—Fe1—C6—C1081.1 (2)C6—C11—C12—C13−176.4 (2)
C9—Fe1—C6—C1037.6 (2)O1—C12—C13—C14−179.0 (3)
C7—Fe1—C6—C10118.9 (3)C11—C12—C13—C14−0.1 (4)
C2—Fe1—C6—C10−76.6 (3)C12—C13—C14—C15−1.4 (4)
C4—Fe1—C6—C10−160.8 (2)C11—N1—C15—C141.9 (4)
C1—Fe1—C6—C10−41.5 (6)C11—N1—C15—C16−176.7 (2)
C5—Fe1—C6—C10162.7 (3)C13—C14—C15—N10.5 (4)
C3—Fe1—C6—C10−117.7 (2)C13—C14—C15—C16179.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.821.962.774 (3)169
C7—H7···O10.982.392.866 (4)109

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2173).

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.
  • Hayashi, T. & Togni, A. (1995). Editors. Ferrocenes VCH: Weinhein: VCH.
  • Kealy, T. J. & Pauson, P. L. (1951). Nature (London), 168, 1039–1040.
  • 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]
  • Staveren, D. R. V. & Metzler-Nolte, N. (2004). Chem. Rev.104, 5931–5985. [PubMed]
  • Xu, C., Gong, J. F. & Wu, Y. J. (2007). Tetrahedron Lett.48, 1619–1623.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography