metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-Ferrocenyl-6-(3-nitro­phen­yl)quinoline

aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Henan, Zhengzhou 450001, People's Republic of China, and bSchool of Food and Bioengineering, Zhengzhou, University of Light Industry, Henan, Zhengzhou 450052, People's Republic of China
*Correspondence e-mail: xqhao@zzu.edu.cn

(Received 10 February 2014; accepted 3 March 2014; online 8 March 2014)

In the title compound, [Fe(C5H5)(C20H13N2O2)], the substituted cyclo­penta­dienyl ring and quinoline system are approximately coplanar, making a dihedral angle of 5.18 (6)°, while the dihedral angle between the quinoline system and the benzene ring is 28.45 (8)°. There is high thermal motion in the free cyclo­penta­dienyl ring compared with the substituted cyclo­penta­dienyl ring. The conformation of the two cyclopentadienyl rings in the ferrocenyl moiety is eclipsed.

Related literature

For ferrocenyl derivatives, see: Staveren & Metzler-Nolte (2004[Staveren, D. R. & Metzler-Nolte, N. (2004). Chem. Rev. 104, 5931-5986.]); Stepnicka (2008[Stepnicka, P. (2008). Ferrocenes: Ligands, Materials and Biomolecules. John Wiley & Sons, Inc.: New York.]); Xu et al. (2010[Xu, C., Zhang, Y. P., Wang, Z. Q., Fu, W. J., Hao, X. Q., Xu, Y. & Ji, B. M. (2010). Chem. Commun. 46, 6852-6854.]). For quinolines, see: Carey et al. (2006[Carey, J. S., Laffan, D., Thomson, C. & Williams, M. T. (2006). Org. Biomol. Chem. 4, 2337-2347.]); Michael (2007[Michael, J. P. (2007). Nat. Prod. Rep. 24, 223-246.]). For the synthesis, see: Xu et al. (2013[Xu, C., Hao, X. Q., Xiao, Z. Q., Wang, Z. Q., Yuan, X. E., Fu, W. J., Ji, B. M. & Song, M. P. (2013). J. Org. Chem. 78, 8730-8738.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C20H13N2O2)]

  • Mr = 434.26

  • Monoclinic, P 21 /c

  • a = 12.0523 (15) Å

  • b = 6.6997 (8) Å

  • c = 23.918 (3) Å

  • β = 91.018 (2)°

  • V = 1931.0 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.81 mm−1

  • T = 296 K

  • 0.41 × 0.32 × 0.25 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.733, Tmax = 0.824

  • 10490 measured reflections

  • 3478 independent reflections

  • 2591 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.092

  • S = 1.01

  • 3478 reflections

  • 271 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In recent years, there has been an increasing interest in the design of new ferrocenyl derivatives, owing to their utility in diverse fields of chemistry, such as organic synthesis, catalysis and materials science (Staveren & Metzler-Nolte 2004; Stepnicka 2008; Xu et al., 2010). In addition, quinolines and their derivatives are important natural products (Carey et al., 2006; Michael 2007). Here we report the crystal structure of the title compound, derived from the via A-alkylation and Suzuki reaction of acetylferrocene, (2-amino-5-bromophenyl)methanol and 3-nitrylphenylboronic acid.

A view on the molecular structure of the title compound is given in Fig. 1. The two cyclopentadienyl rings are almost parallel (dihedral angle of 0.94 (3)°). The substituted cyclopentadienyl and quinolinyl ring are approximately coplanar, making dihedral angle of 5.18 (6)°, and the dihedral angle between the quinolinyl and phenyl ring is 28.45 (8)°.

Related literature top

For ferrocenyl derivatives, see: Staveren & Metzler-Nolte (2004); Stepnicka (2008); Xu et al. (2010). For quinolines, see: Carey et al. (2006); Michael (2007). For the synthesis, see: Xu et al. (2013).

Experimental top

The title compound was prepared as described in literature (Xu et al. 2013) and recrystallized from dichloromethane/petroleum ether solution at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Refinement top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level.
2-Ferrocenyl-6-(3-nitrophenyl)quinoline top
Crystal data top
[Fe(C5H5)(C20H13N2O2)]F(000) = 896
Mr = 434.26Dx = 1.494 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2663 reflections
a = 12.0523 (15) Åθ = 2.4–24.2°
b = 6.6997 (8) ŵ = 0.81 mm1
c = 23.918 (3) ÅT = 296 K
β = 91.018 (2)°Block, red
V = 1931.0 (4) Å30.41 × 0.32 × 0.25 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3478 independent reflections
Radiation source: fine-focus sealed tube2591 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
phi and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1414
Tmin = 0.733, Tmax = 0.824k = 77
10490 measured reflectionsl = 2828
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0347P)2 + 1.1805P]
where P = (Fo2 + 2Fc2)/3
3478 reflections(Δ/σ)max = 0.018
271 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
[Fe(C5H5)(C20H13N2O2)]V = 1931.0 (4) Å3
Mr = 434.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.0523 (15) ŵ = 0.81 mm1
b = 6.6997 (8) ÅT = 296 K
c = 23.918 (3) Å0.41 × 0.32 × 0.25 mm
β = 91.018 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3478 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
2591 reflections with I > 2σ(I)
Tmin = 0.733, Tmax = 0.824Rint = 0.029
10490 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.01Δρmax = 0.25 e Å3
3478 reflectionsΔρmin = 0.33 e Å3
271 parameters
Special details top

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) top
xyzUiso*/Ueq
Fe10.48569 (3)0.34296 (6)0.382218 (16)0.04797 (15)
N11.19484 (19)0.4758 (4)0.00580 (10)0.0552 (6)
N20.75102 (16)0.3060 (3)0.29398 (9)0.0424 (5)
O11.2363 (2)0.5509 (4)0.03524 (9)0.0823 (7)
O21.2073 (2)0.3023 (4)0.01888 (10)0.0812 (7)
C11.1192 (2)0.8036 (4)0.02870 (12)0.0511 (7)
H11.15800.85800.00090.061*
C21.07022 (19)0.5188 (4)0.08508 (10)0.0407 (6)
H21.07800.38310.09250.049*
C31.1253 (2)0.6038 (4)0.04103 (10)0.0417 (6)
C40.9954 (2)0.8381 (4)0.10550 (11)0.0496 (7)
H40.95010.91950.12680.060*
C51.0530 (2)0.9205 (4)0.06205 (12)0.0565 (8)
H51.04731.05670.05500.068*
C61.00316 (19)0.6358 (4)0.11839 (10)0.0381 (6)
C70.91613 (19)0.6649 (4)0.21141 (10)0.0399 (6)
H70.94330.79460.21380.048*
C80.85097 (19)0.5899 (4)0.25508 (10)0.0371 (6)
C90.81385 (18)0.3900 (4)0.25303 (10)0.0374 (6)
C100.8399 (2)0.2741 (4)0.20579 (11)0.0429 (6)
H100.81580.14250.20350.051*
C110.9000 (2)0.3533 (4)0.16343 (11)0.0427 (6)
H110.91480.27490.13240.051*
C120.94044 (18)0.5517 (4)0.16546 (10)0.0375 (6)
C130.8167 (2)0.7074 (4)0.30100 (11)0.0446 (6)
H130.83840.84040.30390.053*
C140.7524 (2)0.6244 (4)0.34049 (11)0.0462 (7)
H140.72810.70080.37030.055*
C150.72202 (19)0.4201 (4)0.33620 (10)0.0407 (6)
C170.65424 (19)0.3269 (4)0.37962 (11)0.0438 (6)
C180.6198 (2)0.4143 (5)0.43104 (11)0.0515 (7)
H180.63930.54820.44450.062*
C190.5526 (2)0.2750 (5)0.45884 (12)0.0619 (8)
H190.51700.29550.49490.074*
C200.5448 (3)0.1018 (5)0.42547 (13)0.0670 (9)
H200.50260.01880.43440.080*
C210.6071 (2)0.1327 (4)0.37660 (12)0.0559 (8)
H210.61580.03730.34590.067*
C220.3303 (4)0.4402 (15)0.3922 (2)0.126 (2)
H220.29290.45050.42810.151*
C230.3859 (5)0.3224 (11)0.3142 (2)0.1147 (18)
H230.39540.23060.28270.138*
C240.3271 (3)0.2868 (10)0.3600 (3)0.1131 (18)
H240.28720.16270.36770.136*
C250.4280 (3)0.5081 (14)0.3183 (3)0.135 (3)
H250.47240.57730.29040.162*
C260.3912 (6)0.5869 (8)0.3687 (4)0.147 (3)
H260.40400.72180.38330.176*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0360 (2)0.0635 (3)0.0444 (2)0.00707 (19)0.00264 (16)0.0053 (2)
N10.0543 (14)0.0625 (18)0.0490 (14)0.0005 (13)0.0113 (11)0.0034 (13)
N20.0354 (11)0.0452 (13)0.0466 (13)0.0026 (10)0.0048 (10)0.0012 (10)
O10.1055 (18)0.0832 (17)0.0598 (14)0.0021 (14)0.0434 (13)0.0112 (13)
O20.1048 (18)0.0609 (16)0.0795 (16)0.0234 (13)0.0436 (14)0.0120 (13)
C10.0530 (16)0.0513 (19)0.0490 (16)0.0093 (14)0.0012 (13)0.0103 (14)
C20.0420 (14)0.0371 (15)0.0431 (14)0.0007 (11)0.0010 (11)0.0036 (12)
C30.0395 (14)0.0480 (17)0.0376 (14)0.0018 (12)0.0005 (11)0.0010 (12)
C40.0537 (16)0.0427 (17)0.0525 (17)0.0030 (13)0.0029 (13)0.0015 (14)
C50.0687 (19)0.0399 (17)0.0608 (18)0.0014 (14)0.0010 (15)0.0088 (14)
C60.0359 (13)0.0386 (15)0.0397 (13)0.0016 (11)0.0027 (10)0.0012 (12)
C70.0354 (13)0.0360 (15)0.0483 (15)0.0029 (11)0.0000 (11)0.0017 (12)
C80.0301 (12)0.0392 (15)0.0419 (14)0.0019 (10)0.0017 (10)0.0040 (11)
C90.0292 (12)0.0414 (16)0.0414 (14)0.0010 (10)0.0002 (10)0.0017 (11)
C100.0439 (14)0.0329 (15)0.0520 (16)0.0011 (11)0.0048 (12)0.0036 (12)
C110.0450 (14)0.0390 (16)0.0441 (14)0.0012 (12)0.0065 (12)0.0069 (12)
C120.0314 (12)0.0400 (15)0.0411 (14)0.0027 (11)0.0008 (10)0.0004 (12)
C130.0458 (15)0.0413 (16)0.0466 (15)0.0040 (12)0.0003 (12)0.0062 (12)
C140.0456 (15)0.0512 (18)0.0419 (15)0.0011 (13)0.0043 (12)0.0073 (13)
C150.0305 (12)0.0496 (17)0.0421 (14)0.0006 (11)0.0007 (11)0.0001 (12)
C170.0336 (13)0.0534 (18)0.0444 (15)0.0022 (12)0.0002 (11)0.0034 (13)
C180.0418 (15)0.070 (2)0.0424 (15)0.0027 (14)0.0003 (12)0.0001 (14)
C190.0558 (18)0.084 (2)0.0461 (17)0.0022 (17)0.0056 (14)0.0113 (17)
C200.072 (2)0.065 (2)0.064 (2)0.0063 (17)0.0115 (17)0.0228 (17)
C210.0610 (18)0.0496 (19)0.0574 (18)0.0014 (14)0.0090 (14)0.0073 (14)
C220.065 (3)0.235 (8)0.078 (3)0.065 (4)0.002 (2)0.016 (4)
C230.090 (3)0.187 (6)0.066 (3)0.032 (4)0.030 (3)0.032 (3)
C240.052 (2)0.148 (5)0.139 (5)0.037 (3)0.030 (3)0.041 (4)
C250.047 (2)0.217 (7)0.140 (5)0.007 (4)0.012 (3)0.126 (5)
C260.122 (5)0.073 (3)0.241 (9)0.029 (3)0.112 (6)0.017 (4)
Geometric parameters (Å, º) top
Fe1—C222.001 (4)C8—C131.419 (3)
Fe1—C252.001 (4)C9—C101.411 (3)
Fe1—C242.010 (4)C10—C111.364 (3)
Fe1—C232.011 (4)C10—H100.9300
Fe1—C262.015 (5)C11—C121.416 (3)
Fe1—C182.035 (3)C11—H110.9300
Fe1—C212.037 (3)C13—C141.353 (3)
Fe1—C172.036 (2)C13—H130.9300
Fe1—C202.040 (3)C14—C151.420 (4)
Fe1—C192.041 (3)C14—H140.9300
N1—O21.213 (3)C15—C171.472 (3)
N1—O11.218 (3)C17—C211.421 (4)
N1—C31.474 (3)C17—C181.430 (4)
N2—C151.319 (3)C18—C191.410 (4)
N2—C91.370 (3)C18—H180.9800
C1—C31.372 (4)C19—C201.411 (5)
C1—C51.382 (4)C19—H190.9800
C1—H10.9300C20—C211.416 (4)
C2—C31.378 (3)C20—H200.9800
C2—C61.388 (3)C21—H210.9800
C2—H20.9300C22—C241.284 (7)
C4—C51.376 (4)C22—C261.354 (8)
C4—C61.393 (3)C22—H220.9800
C4—H40.9300C23—C241.337 (7)
C5—H50.9300C23—C251.347 (8)
C6—C121.479 (3)C23—H230.9800
C7—C121.372 (3)C24—H240.9800
C7—C81.410 (3)C25—C261.396 (8)
C7—H70.9300C25—H250.9800
C8—C91.413 (3)C26—H260.9800
C22—Fe1—C2566.3 (2)C11—C10—H10119.7
C22—Fe1—C2437.3 (2)C9—C10—H10119.7
C25—Fe1—C2465.5 (2)C10—C11—C12121.8 (2)
C22—Fe1—C2364.61 (19)C10—C11—H11119.1
C25—Fe1—C2339.2 (2)C12—C11—H11119.1
C24—Fe1—C2338.8 (2)C7—C12—C11117.9 (2)
C22—Fe1—C2639.4 (2)C7—C12—C6121.2 (2)
C25—Fe1—C2640.7 (2)C11—C12—C6120.8 (2)
C24—Fe1—C2665.0 (2)C14—C13—C8119.4 (2)
C23—Fe1—C2666.3 (2)C14—C13—H13120.3
C22—Fe1—C18126.2 (2)C8—C13—H13120.3
C25—Fe1—C18124.8 (2)C13—C14—C15119.8 (2)
C24—Fe1—C18159.7 (2)C13—C14—H14120.1
C23—Fe1—C18159.8 (2)C15—C14—H14120.1
C26—Fe1—C18110.03 (17)N2—C15—C14122.9 (2)
C22—Fe1—C21155.2 (3)N2—C15—C17116.9 (2)
C25—Fe1—C21124.9 (3)C14—C15—C17120.2 (2)
C24—Fe1—C21122.3 (2)C21—C17—C18107.3 (2)
C23—Fe1—C21108.60 (17)C21—C17—C15125.4 (2)
C26—Fe1—C21162.7 (3)C18—C17—C15127.3 (3)
C18—Fe1—C2168.65 (12)C21—C17—Fe169.60 (15)
C22—Fe1—C17163.1 (3)C18—C17—Fe169.37 (14)
C25—Fe1—C17109.82 (14)C15—C17—Fe1124.45 (18)
C24—Fe1—C17157.9 (2)C19—C18—C17108.2 (3)
C23—Fe1—C17123.65 (18)C19—C18—Fe169.99 (17)
C26—Fe1—C17126.8 (3)C17—C18—Fe169.50 (15)
C18—Fe1—C1741.13 (10)C19—C18—H18125.9
C21—Fe1—C1740.84 (11)C17—C18—H18125.9
C22—Fe1—C20121.1 (3)Fe1—C18—H18125.9
C25—Fe1—C20159.8 (3)C20—C19—C18108.1 (3)
C24—Fe1—C20107.92 (18)C20—C19—Fe169.75 (18)
C23—Fe1—C20123.7 (2)C18—C19—Fe169.53 (16)
C26—Fe1—C20156.2 (3)C20—C19—H19125.9
C18—Fe1—C2068.18 (13)C18—C19—H19125.9
C21—Fe1—C2040.64 (11)Fe1—C19—H19125.9
C17—Fe1—C2068.55 (12)C19—C20—C21108.4 (3)
C22—Fe1—C19108.77 (16)C19—C20—Fe169.79 (18)
C25—Fe1—C19159.3 (3)C21—C20—Fe169.56 (17)
C24—Fe1—C19123.70 (19)C19—C20—H20125.8
C23—Fe1—C19158.9 (3)C21—C20—H20125.8
C26—Fe1—C19122.6 (3)Fe1—C20—H20125.8
C18—Fe1—C1940.48 (11)C20—C21—C17108.0 (3)
C21—Fe1—C1968.41 (13)C20—C21—Fe169.81 (18)
C17—Fe1—C1968.71 (11)C17—C21—Fe169.56 (15)
C20—Fe1—C1940.45 (13)C20—C21—H21126.0
O2—N1—O1123.6 (3)C17—C21—H21126.0
O2—N1—C3118.6 (2)Fe1—C21—H21126.0
O1—N1—C3117.8 (3)C24—C22—C26110.1 (5)
C15—N2—C9117.8 (2)C24—C22—Fe171.7 (3)
C3—C1—C5117.3 (3)C26—C22—Fe170.9 (3)
C3—C1—H1121.4C24—C22—H22125.0
C5—C1—H1121.4C26—C22—H22124.9
C3—C2—C6119.9 (2)Fe1—C22—H22125.0
C3—C2—H2120.0C24—C23—C25108.0 (5)
C6—C2—H2120.0C24—C23—Fe170.5 (2)
C1—C3—C2122.9 (2)C25—C23—Fe170.0 (3)
C1—C3—N1118.3 (2)C24—C23—H23126.0
C2—C3—N1118.9 (2)C25—C23—H23126.0
C5—C4—C6121.6 (3)Fe1—C23—H23126.0
C5—C4—H4119.2C22—C24—C23109.8 (5)
C6—C4—H4119.2C22—C24—Fe170.9 (3)
C4—C5—C1120.9 (3)C23—C24—Fe170.6 (2)
C4—C5—H5119.6C22—C24—H24125.1
C1—C5—H5119.6C23—C24—H24125.1
C2—C6—C4117.4 (2)Fe1—C24—H24125.1
C2—C6—C12122.2 (2)C23—C25—C26106.8 (5)
C4—C6—C12120.4 (2)C23—C25—Fe170.8 (3)
C12—C7—C8121.7 (2)C26—C25—Fe170.2 (3)
C12—C7—H7119.1C23—C25—H25126.6
C8—C7—H7119.1C26—C25—H25126.6
C7—C8—C9119.5 (2)Fe1—C25—H25126.6
C7—C8—C13123.3 (2)C22—C26—C25105.4 (5)
C9—C8—C13117.2 (2)C22—C26—Fe169.7 (3)
N2—C9—C10118.7 (2)C25—C26—Fe169.1 (3)
N2—C9—C8122.9 (2)C22—C26—H26127.3
C10—C9—C8118.4 (2)C25—C26—H26127.3
C11—C10—C9120.6 (2)Fe1—C26—H26127.3
C5—C1—C3—C21.0 (4)C23—Fe1—C20—C2179.2 (3)
C5—C1—C3—N1179.6 (2)C26—Fe1—C20—C21172.6 (4)
C6—C2—C3—C11.4 (4)C18—Fe1—C20—C2182.20 (19)
C6—C2—C3—N1179.2 (2)C17—Fe1—C20—C2137.79 (18)
O2—N1—C3—C1174.6 (3)C19—Fe1—C20—C21119.7 (3)
O1—N1—C3—C15.8 (4)C19—C20—C21—C170.1 (4)
O2—N1—C3—C24.8 (4)Fe1—C20—C21—C1759.3 (2)
O1—N1—C3—C2174.8 (2)C19—C20—C21—Fe159.2 (2)
C6—C4—C5—C11.4 (4)C18—C17—C21—C200.0 (3)
C3—C1—C5—C40.4 (4)C15—C17—C21—C20177.8 (2)
C3—C2—C6—C40.4 (4)Fe1—C17—C21—C2059.4 (2)
C3—C2—C6—C12178.8 (2)C18—C17—C21—Fe159.39 (18)
C5—C4—C6—C21.0 (4)C15—C17—C21—Fe1118.4 (2)
C5—C4—C6—C12179.8 (2)C22—Fe1—C21—C2050.9 (5)
C12—C7—C8—C93.1 (4)C25—Fe1—C21—C20160.8 (3)
C12—C7—C8—C13174.8 (2)C24—Fe1—C21—C2079.8 (3)
C15—N2—C9—C10176.1 (2)C23—Fe1—C21—C20120.4 (3)
C15—N2—C9—C81.9 (3)C26—Fe1—C21—C20169.9 (6)
C7—C8—C9—N2179.5 (2)C18—Fe1—C21—C2081.0 (2)
C13—C8—C9—N22.5 (4)C17—Fe1—C21—C20119.3 (3)
C7—C8—C9—C102.5 (3)C19—Fe1—C21—C2037.30 (19)
C13—C8—C9—C10175.4 (2)C22—Fe1—C21—C17170.2 (4)
N2—C9—C10—C11178.5 (2)C25—Fe1—C21—C1779.9 (3)
C8—C9—C10—C110.4 (4)C24—Fe1—C21—C17160.9 (2)
C9—C10—C11—C121.3 (4)C23—Fe1—C21—C17120.3 (3)
C8—C7—C12—C111.4 (4)C26—Fe1—C21—C1750.6 (6)
C8—C7—C12—C6176.3 (2)C18—Fe1—C21—C1738.33 (16)
C10—C11—C12—C70.8 (4)C20—Fe1—C21—C17119.3 (3)
C10—C11—C12—C6178.5 (2)C19—Fe1—C21—C1781.99 (18)
C2—C6—C12—C7150.7 (2)C25—Fe1—C22—C2480.2 (4)
C4—C6—C12—C730.1 (4)C23—Fe1—C22—C2436.9 (4)
C2—C6—C12—C1131.7 (3)C26—Fe1—C22—C24119.8 (5)
C4—C6—C12—C11147.5 (3)C18—Fe1—C22—C24163.1 (3)
C7—C8—C13—C14178.7 (2)C21—Fe1—C22—C2442.4 (6)
C9—C8—C13—C140.8 (4)C17—Fe1—C22—C24160.2 (4)
C8—C13—C14—C151.4 (4)C20—Fe1—C22—C2478.6 (4)
C9—N2—C15—C140.5 (4)C19—Fe1—C22—C24121.4 (4)
C9—N2—C15—C17179.8 (2)C25—Fe1—C22—C2639.6 (4)
C13—C14—C15—N22.1 (4)C24—Fe1—C22—C26119.8 (5)
C13—C14—C15—C17178.5 (2)C23—Fe1—C22—C2682.9 (4)
N2—C15—C17—C217.7 (4)C18—Fe1—C22—C2677.1 (5)
C14—C15—C17—C21171.6 (3)C21—Fe1—C22—C26162.2 (4)
N2—C15—C17—C18174.9 (2)C17—Fe1—C22—C2640.4 (8)
C14—C15—C17—C185.8 (4)C20—Fe1—C22—C26161.6 (4)
N2—C15—C17—Fe196.0 (3)C19—Fe1—C22—C26118.8 (4)
C14—C15—C17—Fe183.4 (3)C22—Fe1—C23—C2435.5 (4)
C22—Fe1—C17—C21165.7 (6)C25—Fe1—C23—C24118.5 (5)
C25—Fe1—C17—C21120.9 (4)C26—Fe1—C23—C2479.0 (4)
C24—Fe1—C17—C2147.3 (5)C18—Fe1—C23—C24162.7 (5)
C23—Fe1—C17—C2179.4 (3)C21—Fe1—C23—C24118.7 (4)
C26—Fe1—C17—C21163.4 (4)C17—Fe1—C23—C24161.4 (4)
C18—Fe1—C17—C21118.6 (2)C20—Fe1—C23—C2476.2 (4)
C20—Fe1—C17—C2137.61 (18)C19—Fe1—C23—C2440.6 (7)
C19—Fe1—C17—C2181.20 (19)C22—Fe1—C23—C2582.9 (4)
C22—Fe1—C17—C1847.2 (6)C24—Fe1—C23—C25118.5 (5)
C25—Fe1—C17—C18120.6 (4)C26—Fe1—C23—C2539.5 (3)
C24—Fe1—C17—C18165.9 (4)C18—Fe1—C23—C2544.2 (7)
C23—Fe1—C17—C18162.0 (3)C21—Fe1—C23—C25122.8 (4)
C26—Fe1—C17—C1878.1 (4)C17—Fe1—C23—C2580.1 (4)
C21—Fe1—C17—C18118.6 (2)C20—Fe1—C23—C25165.3 (4)
C20—Fe1—C17—C1880.96 (19)C19—Fe1—C23—C25159.1 (5)
C19—Fe1—C17—C1837.37 (18)C26—C22—C24—C230.6 (6)
C22—Fe1—C17—C1574.7 (6)Fe1—C22—C24—C2360.2 (3)
C25—Fe1—C17—C151.3 (4)C26—C22—C24—Fe160.8 (4)
C24—Fe1—C17—C1572.3 (5)C25—C23—C24—C220.1 (6)
C23—Fe1—C17—C1540.2 (4)Fe1—C23—C24—C2260.4 (4)
C26—Fe1—C17—C1543.7 (4)C25—C23—C24—Fe160.2 (3)
C18—Fe1—C17—C15121.8 (3)C25—Fe1—C24—C2282.4 (4)
C21—Fe1—C17—C15119.6 (3)C23—Fe1—C24—C22120.0 (5)
C20—Fe1—C17—C15157.2 (3)C26—Fe1—C24—C2237.4 (4)
C19—Fe1—C17—C15159.2 (3)C18—Fe1—C24—C2242.7 (7)
C21—C17—C18—C190.0 (3)C21—Fe1—C24—C22160.5 (4)
C15—C17—C18—C19177.7 (2)C17—Fe1—C24—C22164.9 (4)
Fe1—C17—C18—C1959.50 (19)C20—Fe1—C24—C22118.1 (4)
C21—C17—C18—Fe159.53 (19)C19—Fe1—C24—C2276.3 (4)
C15—C17—C18—Fe1118.2 (3)C22—Fe1—C24—C23120.0 (5)
C22—Fe1—C18—C1975.9 (4)C25—Fe1—C24—C2337.6 (4)
C25—Fe1—C18—C19160.2 (3)C26—Fe1—C24—C2382.6 (4)
C24—Fe1—C18—C1945.2 (6)C18—Fe1—C24—C23162.7 (5)
C23—Fe1—C18—C19167.3 (5)C21—Fe1—C24—C2379.5 (4)
C26—Fe1—C18—C19117.1 (4)C17—Fe1—C24—C2344.9 (7)
C21—Fe1—C18—C1981.3 (2)C20—Fe1—C24—C23121.8 (4)
C17—Fe1—C18—C19119.4 (3)C19—Fe1—C24—C23163.6 (4)
C20—Fe1—C18—C1937.49 (19)C24—C23—C25—C260.8 (5)
C22—Fe1—C18—C17164.7 (3)Fe1—C23—C25—C2661.4 (3)
C25—Fe1—C18—C1780.4 (4)C24—C23—C25—Fe160.6 (3)
C24—Fe1—C18—C17164.6 (5)C22—Fe1—C25—C2378.3 (4)
C23—Fe1—C18—C1747.9 (6)C24—Fe1—C25—C2337.3 (3)
C26—Fe1—C18—C17123.5 (4)C26—Fe1—C25—C23116.7 (5)
C21—Fe1—C18—C1738.07 (16)C18—Fe1—C25—C23162.9 (3)
C20—Fe1—C18—C1781.92 (18)C21—Fe1—C25—C2376.2 (3)
C19—Fe1—C18—C17119.4 (3)C17—Fe1—C25—C23119.3 (3)
C17—C18—C19—C200.1 (3)C20—Fe1—C25—C2337.8 (6)
Fe1—C18—C19—C2059.3 (2)C19—Fe1—C25—C23158.6 (4)
C17—C18—C19—Fe159.20 (18)C22—Fe1—C25—C2638.4 (3)
C22—Fe1—C19—C20116.3 (4)C24—Fe1—C25—C2679.5 (4)
C25—Fe1—C19—C20171.4 (4)C23—Fe1—C25—C26116.7 (5)
C24—Fe1—C19—C2077.8 (3)C18—Fe1—C25—C2680.3 (4)
C23—Fe1—C19—C2048.4 (5)C21—Fe1—C25—C26167.1 (4)
C26—Fe1—C19—C20157.6 (4)C17—Fe1—C25—C26123.9 (4)
C18—Fe1—C19—C20119.4 (3)C20—Fe1—C25—C26154.5 (5)
C21—Fe1—C19—C2037.47 (18)C19—Fe1—C25—C2641.9 (6)
C17—Fe1—C19—C2081.50 (19)C24—C22—C26—C251.0 (6)
C22—Fe1—C19—C18124.3 (4)Fe1—C22—C26—C2560.3 (3)
C25—Fe1—C19—C1851.9 (5)C24—C22—C26—Fe161.3 (4)
C24—Fe1—C19—C18162.8 (3)C23—C25—C26—C221.1 (5)
C23—Fe1—C19—C18167.8 (4)Fe1—C25—C26—C2260.7 (3)
C26—Fe1—C19—C1883.0 (4)C23—C25—C26—Fe161.8 (3)
C21—Fe1—C19—C1881.98 (19)C25—Fe1—C26—C22116.4 (5)
C17—Fe1—C19—C1837.95 (17)C24—Fe1—C26—C2235.5 (3)
C20—Fe1—C19—C18119.4 (3)C23—Fe1—C26—C2278.3 (4)
C18—C19—C20—C210.1 (4)C18—Fe1—C26—C22123.2 (4)
Fe1—C19—C20—C2159.0 (2)C21—Fe1—C26—C22154.4 (5)
C18—C19—C20—Fe159.1 (2)C17—Fe1—C26—C22166.4 (3)
C22—Fe1—C20—C1982.6 (3)C20—Fe1—C26—C2242.0 (7)
C25—Fe1—C20—C19171.2 (4)C19—Fe1—C26—C2279.9 (4)
C24—Fe1—C20—C19121.3 (3)C22—Fe1—C26—C25116.4 (5)
C23—Fe1—C20—C19161.1 (2)C24—Fe1—C26—C2580.9 (4)
C26—Fe1—C20—C1952.9 (5)C23—Fe1—C26—C2538.1 (3)
C18—Fe1—C20—C1937.52 (17)C18—Fe1—C26—C25120.4 (4)
C21—Fe1—C20—C19119.7 (3)C21—Fe1—C26—C2538.1 (8)
C17—Fe1—C20—C1981.92 (19)C17—Fe1—C26—C2577.2 (4)
C22—Fe1—C20—C21157.7 (3)C20—Fe1—C26—C25158.4 (5)
C25—Fe1—C20—C2151.5 (5)C19—Fe1—C26—C25163.7 (4)
C24—Fe1—C20—C21119.0 (3)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C20H13N2O2)]
Mr434.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)12.0523 (15), 6.6997 (8), 23.918 (3)
β (°) 91.018 (2)
V3)1931.0 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.81
Crystal size (mm)0.41 × 0.32 × 0.25
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.733, 0.824
No. of measured, independent and
observed [I > 2σ(I)] reflections
10490, 3478, 2591
Rint0.029
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.092, 1.01
No. of reflections3478
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.33

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was sponsored by the National Natural Science Foundation of China (No. 21102135).

References

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