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ISSN: 2056-9890

1,1′-Bis(1-acetyl-5-methyl-1H-pyrazol-3-yl)ferrocene

aDepartment of Chemical Engineering, Nantong Vocational College, Nantong 226007, People's Republic of China, bCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, cAnalytical Center, China Pharmaceutical University, Nanjin 210009, People's Republic of China, and dHubei Research Institue of Geophysics Survey and Design, Wuhan 430056, People's Republic of China
*Correspondence e-mail: ycshi@yzu.edu.cn

(Received 28 September 2011; accepted 11 October 2011; online 12 October 2011)

The title compound, [Fe(C11H11N2O)2], crystallizes with two independent mol­ecules in the asymmetric unit which have have different conformations. In one mol­ecule, the two ferrocene cyclo­penta­dienyl rings are fully eclipsed and the two pyrazole rings are syn to each other; in the other, the two cyclo­penta­dienyl rings are synclinal and the pyrazole rings are anti. In both mol­ecules, the acetyl group attached to the pyrazole ring is oriented away from the iron–cyclo­penta­dienyl group of ferrocene.

Related literature

For background to pyrazole compounds in coordination chemistry, supra­molecular chemistry and organometallic chemistry, see: Chakrabarty et al. (2004[Chakrabarty, S., Poddar, R. K., Poulsen, R. D., Thompson, A. L. & Howard, J. A. K. (2004). Acta Cryst. C60, m628-m630.]); Miranda et al. (2005[Miranda, C., Escartí, F., Lamarque, L., García-España, E., Navarro, P., Latorre, J., Lloret, F., Jiménez, H. R. & Yunta, M. J. R. (2005). Eur. J. Inorg. Chem. pp. 189-208.]); Esquius et al. (2001[Esquius, G., Pons, J., Yáñez, R. & Ros, J. (2001). J. Organomet. Chem. 619, 14-23.]). For related structures, see: Shi et al. (2005[Shi, Y.-C., Sui, C.-X. & Cheng, H.-J. (2005). Acta Cryst. E61, m1563-m1565.], 2006a[Shi, Y.-C., Zhu, B.-B. & Sui, C.-X. (2006a). Acta Cryst. E62, m2389-m2391.],b[Shi, Y.-C., Zhu, B.-B. & Sui, C.-X. (2006b). Acta Cryst. E62, m2461-m2463.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C11H11N2O)2]

  • Mr = 430.29

  • Monoclinic, P 21 /n

  • a = 10.9021 (19) Å

  • b = 12.7992 (16) Å

  • c = 27.9421 (14) Å

  • β = 90.492 (16)°

  • V = 3898.8 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.80 mm−1

  • T = 295 K

  • 0.22 × 0.18 × 0.11 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.832, Tmax = 0.907

  • 8056 measured reflections

  • 7639 independent reflections

  • 4199 reflections with I > 2σ(I)

  • Rint = 0.032

  • 3 standard reflections every 200 reflections intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.077

  • wR(F2) = 0.160

  • S = 1.07

  • 7639 reflections

  • 529 parameters

  • H-atom parameters constrained

  • Δρmax = 1.31 e Å−3

  • Δρmin = −0.34 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.] and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The title compound, (I), synthesized from the acetylation of 1, 1'-bis(5-methyl-1H-pyrazol-1-yl)ferrocene in the presence of Et3N, crystallizes with two independent molecules (Fig. 1) in the space group P 21/n, and the two molecules are rotamers for each other and have different conformations. For each type of molecules (types a and b), two acetyl groups attached to two pyrazole rings are oriented away from the iron-cyclopentadienyl group of ferrocene. However, two pyrazole rings in Ia are cis whereas both are trans in Ib. Furthermore, the two cyclopentadienyl rings of ferrocene in type Ia are fully eclipsed because the torsion angle C7—C1g—C2g—C16 in Ia (where C1g and C2g are the cycopentadiene ring centroids) is 0.1 (5)° while they are synclinal because the value in type Ib is 7.3 (5)°. The cyclopentadienyl ring and the corresponding pyrazole ring form dihedral angles of 5.4 (3) and 7.7 (3)° for Ia and 3.9 (3) and 3.9 (4)° for Ib. The pyrazole ring and the corresponding acetyl group make dihedral angles of 6.5 (3) and 3.7 (8)° for Ia and 4.3 (7) and 4.5 (8)° for Ib.

As with the reported pyrazole compounds, the bond lengths of each pyrazole ring in (I) indicate electron delocalization (Shi et al., 2005, 2006a, 2006b). In addition, intermolecular C—H···O hydrogen bonds for each of Ia and Ib are present in the crystalline state (Table 1).

Related literature top

For background to pyrazole compounds in coordination chemistry, supramolecular chemistry and organometallic chemistry, see: Chakrabarty et al. (2004); Miranda et al. (2005); Esquius et al. (2001). For related structures, see: Shi et al. (2005, 2006a,b).

Experimental top

A mixture of 80% hydrated hydrazine (28 ml) and Fe(C5H4COCH2COCH3)2 (5.313 g, 15 mmol) was stirred for 24 h at ambient temperature under N2. The orange-yellow solid was collected, washed with water and air-dried to give 1, 1'-bis(5–methyl–1H–pyrazol–1–yl)ferrocene (4.122 g, yield, 79.4%; d.p., 497.75 K).

To a mixture of 1, 1'-bis(5–methyl–1H–pyrazol–1–yl)ferrocene (1.385 g, 4 mmol) and Et3N (3.036 g, 30 mmol) in 10 ml of THF acetyl chloride (2 ml, 28 mmol) in 5 ml of THF was added dropwise and stirred for 1 h at ambient temperature under N2. The resulting filtrate was stripped off solvent and purified by chromatography on silica gel with dichloromethane as an eluant to afford an orange-red solid (0.652 g, yield, 37.9%; m.p., 432.35–433.25 K). Analysis calculated for C22H22FeN4O2: C 61.41, H 5.15, N 13.02%; found: C 61.38, H 5.23, N 13.29%. IR (KBr): 3103 (w, C—H), 1722 (vs, CO), 1580 (m, CN) cm-1. UV (nm, λmax, ε(× 104), in DMF): 263.00 (2.86, B band), 337.00 (0.49, K band), 454.00 (0.07, d-d band). 1H NMR (500 MHz, CDCl3, δ, p.p.m.): 5.965 (s, 2H, 2CH), 4.692, 4.347 (s, 4H, s, 4H, (2H, 5H) and (3H, 4H) of two C5H4 rings), 2.658 (s, 6H, 2COCH3), 2.519 (s, 6H, 2CH3).

Refinement top

All H atoms bonded to parent atoms were placed at geometrically idealized positions and then treated as riding atoms, with C—H distances of 0.93 Å (aromatic), and 0.96 Å (CH3) and with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for methyl groups.

The H atoms of C3 and C20 methyl groups were modelled as six equally spaced half-H atoms.

The final difference Fourier map had peak in the vicinity of the Fe atom.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and WinGX (Farrugia, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing two independent molecules and the 30% probability displacement ellipsoids.
1,1'-Bis(1-acetyl-5-methyl-1H-pyrazol-3-yl)ferrocene top
Crystal data top
[Fe(C11H11N2O)2]F(000) = 1792
Mr = 430.29Dx = 1.466 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 10.9021 (19) Åθ = 9–15°
b = 12.7992 (16) ŵ = 0.80 mm1
c = 27.9421 (14) ÅT = 295 K
β = 90.492 (16)°Prism, red
V = 3898.8 (9) Å30.22 × 0.18 × 0.11 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
4199 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 26.0°, θmin = 1.5°
ω/2θ scansh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 015
Tmin = 0.832, Tmax = 0.907l = 3434
8056 measured reflections3 standard reflections every 200 reflections
7639 independent reflections intensity decay: none
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)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0355P)2 + 7.7275P]
where P = (Fo2 + 2Fc2)/3
7639 reflections(Δ/σ)max = 0.001
529 parametersΔρmax = 1.31 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
[Fe(C11H11N2O)2]V = 3898.8 (9) Å3
Mr = 430.29Z = 8
Monoclinic, P21/nMo Kα radiation
a = 10.9021 (19) ŵ = 0.80 mm1
b = 12.7992 (16) ÅT = 295 K
c = 27.9421 (14) Å0.22 × 0.18 × 0.11 mm
β = 90.492 (16)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
4199 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.032
Tmin = 0.832, Tmax = 0.9073 standard reflections every 200 reflections
8056 measured reflections intensity decay: none
7639 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0770 restraints
wR(F2) = 0.160H-atom parameters constrained
S = 1.07Δρmax = 1.31 e Å3
7639 reflectionsΔρmin = 0.34 e Å3
529 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*/UeqOcc. (<1)
C10.8011 (6)0.9723 (5)0.5909 (3)0.065 (2)
H1A0.85931.02240.57930.097*
H1B0.77940.98950.62320.097*
H1C0.72890.97370.57100.097*
C20.8563 (6)0.8661 (6)0.5897 (2)0.0541 (19)
C30.9242 (5)0.6313 (5)0.5988 (2)0.0502 (18)
H3A0.98380.68650.59750.075*0.50
H3B0.93530.58510.57210.075*0.50
H3C0.93460.59310.62810.075*0.50
H3D0.91870.55660.60100.075*0.50
H3E0.96720.65800.62630.075*0.50
H3F0.96780.65000.57040.075*0.50
C40.7984 (5)0.6769 (5)0.5968 (2)0.0397 (16)
C50.6872 (5)0.6302 (5)0.5976 (2)0.0387 (15)
H50.67200.55890.60020.046*
C60.5983 (5)0.7103 (5)0.5939 (2)0.0373 (15)
C70.4634 (5)0.7007 (5)0.5925 (2)0.0383 (14)
C80.3962 (5)0.6047 (5)0.5905 (2)0.0385 (15)
H80.42990.53790.59080.046*
C90.2693 (6)0.6291 (5)0.5881 (2)0.0431 (16)
H90.20520.58130.58620.052*
C100.2576 (6)0.7397 (5)0.5891 (2)0.0461 (18)
H100.18460.77720.58840.055*
C110.3773 (6)0.7823 (5)0.5911 (2)0.0452 (17)
H110.39600.85320.59150.054*
C120.4054 (5)0.6172 (5)0.4699 (2)0.0394 (15)
H120.43990.55080.46840.047*
C130.2787 (6)0.6403 (6)0.4697 (2)0.0451 (17)
H130.21530.59180.46770.054*
C140.2649 (6)0.7509 (6)0.4729 (2)0.0513 (19)
H140.19140.78770.47340.062*
C150.3853 (6)0.7943 (5)0.4752 (2)0.0469 (16)
H150.40400.86490.47780.056*
C160.4709 (5)0.7125 (5)0.4728 (2)0.0383 (15)
C170.6063 (5)0.7234 (5)0.4717 (2)0.0351 (15)
C180.6946 (5)0.6416 (5)0.4709 (2)0.0353 (14)
H180.67900.57020.47260.042*
C190.8060 (5)0.6879 (5)0.4672 (2)0.0393 (15)
C200.9288 (5)0.6398 (5)0.4641 (2)0.0546 (19)
H20A0.95920.64720.43220.082*
H20B0.92340.56690.47210.082*
H20C0.98380.67390.48620.082*
C210.8154 (6)0.9840 (5)0.4578 (3)0.068 (2)
H21A0.88071.03340.46230.102*
H21B0.75630.99220.48270.102*
H21C0.77660.99590.42730.102*
C220.8660 (6)0.8763 (6)0.4592 (2)0.0537 (19)
C231.0519 (6)0.5653 (5)0.8634 (3)0.063 (2)
H23A1.11430.51260.86180.095*
H23B0.99020.55180.83940.095*
H23C1.01520.56420.89450.095*
C241.1073 (6)0.6692 (5)0.8548 (2)0.0426 (16)
C251.1744 (5)0.8998 (5)0.8297 (2)0.0472 (17)
H25A1.23460.84700.83650.071*0.50
H25B1.18470.95690.85160.071*0.50
H25C1.18450.92450.79750.071*0.50
H25D1.16790.97190.82060.071*0.50
H25E1.21780.86200.80540.071*0.50
H25F1.21800.89440.85950.071*0.50
C261.0483 (5)0.8544 (5)0.8350 (2)0.0358 (14)
C270.9378 (5)0.9004 (5)0.8290 (2)0.0383 (15)
H270.92290.96960.82060.046*
C280.8491 (5)0.8219 (5)0.8380 (2)0.0371 (15)
C290.7148 (5)0.8317 (4)0.8354 (2)0.0324 (14)
C300.6269 (6)0.7532 (5)0.8464 (2)0.0414 (16)
H300.64410.68600.85730.050*
C310.5087 (5)0.7954 (6)0.8378 (2)0.0441 (16)
H310.43490.76000.84160.053*
C320.5208 (5)0.8981 (5)0.8227 (2)0.0506 (18)
H320.45690.94370.81540.061*
C330.6473 (5)0.9213 (5)0.8205 (2)0.0447 (16)
H330.68090.98460.81080.054*
C340.6473 (6)0.6749 (6)0.7340 (2)0.058 (2)
H340.67520.61010.74450.069*
C350.5229 (6)0.7049 (8)0.7279 (3)0.067 (2)
H350.45530.66260.73370.080*
C360.5186 (6)0.8063 (8)0.7119 (2)0.071 (3)
H360.44750.84370.70490.085*
C370.6403 (6)0.8447 (7)0.7078 (2)0.061 (2)
H370.66310.91140.69820.073*
C380.7212 (6)0.7613 (6)0.7214 (2)0.0472 (19)
C390.8554 (6)0.7657 (6)0.7200 (2)0.0454 (18)
C400.9398 (5)0.6853 (5)0.7321 (2)0.0441 (16)
H400.92170.61900.74370.053*
C411.0522 (6)0.7254 (6)0.7234 (2)0.0482 (18)
C421.1760 (6)0.6738 (6)0.7281 (3)0.066 (2)
H42A1.21590.67420.69760.099*
H42B1.16570.60300.73860.099*
H42C1.22510.71130.75100.099*
C431.0738 (6)1.0046 (6)0.6782 (3)0.070 (2)
H43A1.14001.05400.67660.106*
H43B1.01281.02990.69990.106*
H43C1.03790.99600.64700.106*
C441.1211 (6)0.9032 (6)0.6954 (2)0.055 (2)
Fe10.35856 (7)0.69453 (7)0.53118 (3)0.0321 (2)
Fe20.60796 (7)0.79888 (8)0.77673 (3)0.0371 (2)
N10.7739 (5)0.7822 (4)0.59283 (18)0.0423 (13)
N20.6486 (4)0.8042 (4)0.59141 (17)0.0405 (12)
N30.7822 (4)0.7929 (4)0.46589 (17)0.0413 (13)
N40.6573 (4)0.8160 (4)0.46824 (18)0.0455 (13)
N51.0245 (5)0.7520 (4)0.84742 (18)0.0368 (12)
N60.9003 (4)0.7320 (4)0.84904 (17)0.0333 (12)
N71.0347 (4)0.8261 (5)0.70783 (17)0.0443 (14)
N80.9118 (4)0.8515 (5)0.70534 (18)0.0478 (14)
O10.9643 (4)0.8490 (4)0.5868 (2)0.0741 (16)
O20.9741 (4)0.8544 (4)0.4551 (2)0.0821 (18)
O31.2166 (4)0.6856 (4)0.85421 (17)0.0568 (13)
O41.2289 (4)0.8845 (5)0.7002 (2)0.0858 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.048 (4)0.049 (5)0.097 (6)0.016 (4)0.002 (4)0.014 (4)
C20.040 (4)0.073 (5)0.050 (4)0.013 (4)0.004 (3)0.003 (4)
C30.029 (3)0.064 (5)0.058 (4)0.003 (3)0.001 (3)0.005 (4)
C40.032 (3)0.052 (5)0.035 (3)0.002 (3)0.004 (3)0.008 (3)
C50.032 (3)0.042 (4)0.041 (4)0.006 (3)0.000 (3)0.005 (3)
C60.027 (3)0.049 (4)0.036 (3)0.005 (3)0.001 (2)0.006 (3)
C70.033 (3)0.045 (4)0.037 (3)0.001 (3)0.003 (3)0.003 (3)
C80.037 (3)0.038 (4)0.041 (4)0.003 (3)0.001 (3)0.002 (3)
C90.039 (4)0.047 (4)0.044 (4)0.005 (3)0.004 (3)0.006 (3)
C100.031 (4)0.057 (5)0.050 (4)0.005 (3)0.005 (3)0.009 (3)
C110.046 (4)0.041 (4)0.049 (4)0.002 (3)0.006 (3)0.013 (3)
C120.033 (3)0.044 (4)0.041 (4)0.001 (3)0.003 (3)0.009 (3)
C130.036 (4)0.061 (5)0.039 (4)0.007 (3)0.007 (3)0.006 (3)
C140.029 (4)0.071 (5)0.054 (5)0.006 (3)0.006 (3)0.012 (4)
C150.041 (4)0.044 (4)0.056 (4)0.001 (3)0.002 (3)0.011 (4)
C160.026 (3)0.047 (4)0.042 (4)0.005 (3)0.005 (3)0.006 (3)
C170.032 (4)0.041 (4)0.032 (3)0.005 (3)0.004 (3)0.001 (3)
C180.030 (3)0.034 (3)0.042 (4)0.002 (3)0.002 (3)0.001 (3)
C190.029 (3)0.053 (4)0.035 (3)0.001 (3)0.002 (2)0.002 (3)
C200.038 (4)0.063 (5)0.063 (5)0.009 (3)0.003 (3)0.009 (4)
C210.054 (5)0.043 (4)0.107 (7)0.016 (4)0.024 (4)0.004 (4)
C220.041 (4)0.061 (5)0.059 (5)0.018 (4)0.009 (3)0.003 (4)
C230.046 (4)0.043 (4)0.100 (6)0.007 (3)0.009 (4)0.007 (4)
C240.036 (4)0.049 (4)0.043 (4)0.012 (3)0.004 (3)0.000 (3)
C250.033 (3)0.049 (4)0.060 (4)0.006 (3)0.004 (3)0.008 (3)
C260.036 (3)0.039 (4)0.032 (3)0.001 (3)0.002 (3)0.008 (3)
C270.039 (4)0.033 (4)0.043 (4)0.002 (3)0.002 (3)0.005 (3)
C280.027 (3)0.050 (4)0.035 (3)0.004 (3)0.004 (3)0.004 (3)
C290.028 (3)0.035 (4)0.035 (3)0.005 (3)0.001 (2)0.006 (3)
C300.037 (4)0.048 (4)0.039 (4)0.001 (3)0.001 (3)0.006 (3)
C310.021 (3)0.065 (5)0.047 (4)0.004 (3)0.012 (3)0.001 (4)
C320.027 (3)0.051 (4)0.074 (5)0.012 (3)0.004 (3)0.002 (4)
C330.030 (3)0.036 (4)0.068 (5)0.008 (3)0.006 (3)0.008 (3)
C340.038 (4)0.083 (6)0.052 (4)0.013 (4)0.008 (3)0.025 (4)
C350.028 (4)0.120 (7)0.053 (5)0.028 (5)0.002 (3)0.026 (5)
C360.029 (4)0.142 (9)0.041 (4)0.002 (5)0.009 (3)0.010 (5)
C370.035 (4)0.108 (7)0.039 (4)0.004 (4)0.004 (3)0.023 (4)
C380.027 (4)0.083 (5)0.032 (4)0.009 (3)0.004 (3)0.006 (3)
C390.025 (4)0.079 (5)0.032 (4)0.001 (3)0.003 (3)0.011 (3)
C400.033 (3)0.055 (4)0.044 (4)0.005 (3)0.008 (3)0.007 (3)
C410.036 (4)0.068 (5)0.041 (4)0.004 (4)0.002 (3)0.013 (4)
C420.034 (4)0.088 (6)0.076 (5)0.011 (4)0.011 (3)0.016 (5)
C430.046 (5)0.071 (6)0.094 (6)0.020 (4)0.002 (4)0.002 (5)
C440.031 (4)0.087 (6)0.048 (4)0.012 (4)0.007 (3)0.012 (4)
Fe10.0230 (4)0.0347 (5)0.0384 (5)0.0019 (4)0.0011 (3)0.0006 (4)
Fe20.0185 (4)0.0559 (6)0.0369 (5)0.0008 (4)0.0001 (3)0.0032 (5)
N10.034 (3)0.056 (4)0.037 (3)0.008 (3)0.006 (2)0.003 (3)
N20.029 (3)0.048 (3)0.045 (3)0.005 (3)0.004 (2)0.005 (3)
N30.028 (3)0.049 (4)0.047 (3)0.005 (3)0.007 (2)0.009 (3)
N40.032 (3)0.053 (4)0.052 (3)0.003 (3)0.005 (2)0.006 (3)
N50.023 (3)0.044 (3)0.044 (3)0.005 (2)0.000 (2)0.002 (2)
N60.017 (3)0.042 (3)0.041 (3)0.002 (2)0.004 (2)0.001 (2)
N70.015 (2)0.076 (4)0.042 (3)0.004 (3)0.005 (2)0.001 (3)
N80.020 (3)0.076 (4)0.047 (3)0.002 (3)0.004 (2)0.002 (3)
O10.033 (3)0.087 (4)0.103 (4)0.009 (3)0.012 (3)0.006 (3)
O20.027 (3)0.089 (4)0.130 (5)0.016 (3)0.016 (3)0.001 (4)
O30.027 (2)0.064 (3)0.079 (3)0.010 (2)0.002 (2)0.004 (3)
O40.027 (3)0.117 (5)0.114 (5)0.007 (3)0.008 (3)0.005 (4)
Geometric parameters (Å, º) top
C1—C21.488 (9)C23—H23B0.9600
C1—H1A0.9600C23—H23C0.9600
C1—H1B0.9600C24—O31.211 (7)
C1—H1C0.9600C24—N51.406 (7)
C2—O11.202 (7)C25—C261.501 (8)
C2—N11.403 (8)C25—H25A0.9600
C3—C41.491 (8)C25—H25B0.9600
C3—H3A0.9600C25—H25C0.9600
C3—H3B0.9600C25—H25D0.9600
C3—H3C0.9600C25—H25E0.9600
C3—H3D0.9600C25—H25F0.9600
C3—H3E0.9600C26—C271.350 (8)
C3—H3F0.9600C26—N51.381 (7)
C4—C51.352 (8)C27—C281.418 (8)
C4—N11.378 (8)C27—H270.9300
C5—C61.414 (8)C28—N61.314 (7)
C5—H50.9300C28—C291.471 (7)
C6—N21.323 (7)C29—C331.423 (8)
C6—C71.476 (8)C29—C301.424 (8)
C7—C111.404 (8)C29—Fe22.047 (5)
C7—C81.432 (8)C30—C311.416 (8)
C7—Fe12.054 (5)C30—Fe22.042 (6)
C8—C91.420 (8)C30—H300.9300
C8—Fe12.057 (6)C31—C321.387 (9)
C8—H80.9300C31—Fe22.029 (5)
C9—C101.421 (8)C31—H310.9300
C9—Fe12.051 (6)C32—C331.413 (8)
C9—H90.9300C32—Fe22.047 (6)
C10—C111.415 (9)C32—H320.9300
C10—Fe12.047 (6)C33—Fe22.030 (6)
C10—H100.9300C33—H330.9300
C11—Fe12.025 (6)C34—C381.415 (9)
C11—H110.9300C34—C351.418 (9)
C12—C131.413 (8)C34—Fe22.033 (7)
C12—C161.416 (8)C34—H340.9300
C12—Fe12.047 (6)C35—C361.373 (11)
C12—H120.9300C35—Fe22.037 (7)
C13—C141.427 (9)C35—H350.9300
C13—Fe12.042 (6)C36—C371.420 (9)
C13—H130.9300C36—Fe22.052 (6)
C14—C151.426 (9)C36—H360.9300
C14—Fe12.046 (6)C37—C381.434 (9)
C14—H140.9300C37—Fe22.046 (6)
C15—C161.404 (8)C37—H370.9300
C15—Fe12.043 (6)C38—C391.465 (8)
C15—H150.9300C38—Fe22.045 (6)
C16—C171.484 (8)C39—N81.325 (8)
C16—Fe12.061 (6)C39—C401.420 (9)
C17—N41.313 (7)C40—C411.352 (8)
C17—C181.423 (8)C40—H400.9300
C18—C191.357 (8)C41—N71.373 (8)
C18—H180.9300C41—C421.507 (9)
C19—N31.370 (8)C42—H42A0.9600
C19—C201.477 (8)C42—H42B0.9600
C20—H20A0.9600C42—H42C0.9600
C20—H20B0.9600C43—C441.476 (10)
C20—H20C0.9600C43—H43A0.9600
C21—C221.485 (9)C43—H43B0.9600
C21—H21A0.9600C43—H43C0.9600
C21—H21B0.9600C44—O41.206 (7)
C21—H21C0.9600C44—N71.410 (8)
C22—O21.218 (8)N1—N21.396 (7)
C22—N31.418 (8)N3—N41.395 (6)
C23—C241.481 (9)N5—N61.378 (6)
C23—H23A0.9600N7—N81.380 (6)
C2—C1—H1A109.5C30—C31—Fe270.1 (3)
C2—C1—H1B109.5C32—C31—H31125.5
H1A—C1—H1B109.5C30—C31—H31125.5
C2—C1—H1C109.5Fe2—C31—H31125.1
H1A—C1—H1C109.5C31—C32—C33108.0 (5)
H1B—C1—H1C109.5C31—C32—Fe269.4 (3)
O1—C2—N1119.6 (7)C33—C32—Fe269.1 (4)
O1—C2—C1124.4 (7)C31—C32—H32126.0
N1—C2—C1116.0 (6)C33—C32—H32126.0
C4—C3—H3A109.5Fe2—C32—H32127.0
C4—C3—H3B109.5C32—C33—C29108.7 (6)
H3A—C3—H3B109.5C32—C33—Fe270.4 (4)
C4—C3—H3C109.5C29—C33—Fe270.2 (3)
H3A—C3—H3C109.5C32—C33—H33125.7
H3B—C3—H3C109.5C29—C33—H33125.7
C4—C3—H3D109.5Fe2—C33—H33125.4
H3A—C3—H3D141.1C38—C34—C35107.8 (7)
H3B—C3—H3D56.3C38—C34—Fe270.2 (4)
H3C—C3—H3D56.3C35—C34—Fe269.8 (4)
C4—C3—H3E109.5C38—C34—H34126.1
H3A—C3—H3E56.3C35—C34—H34126.1
H3B—C3—H3E141.1Fe2—C34—H34125.5
H3C—C3—H3E56.3C36—C35—C34109.0 (7)
H3D—C3—H3E109.5C36—C35—Fe271.0 (4)
C4—C3—H3F109.5C34—C35—Fe269.5 (4)
H3A—C3—H3F56.3C36—C35—H35125.5
H3B—C3—H3F56.3C34—C35—H35125.5
H3C—C3—H3F141.1Fe2—C35—H35125.6
H3D—C3—H3F109.5C35—C36—C37108.9 (7)
H3E—C3—H3F109.5C35—C36—Fe269.8 (4)
C5—C4—N1105.1 (5)C37—C36—Fe269.5 (4)
C5—C4—C3130.6 (6)C35—C36—H36125.6
N1—C4—C3124.3 (6)C37—C36—H36125.6
C4—C5—C6107.0 (6)Fe2—C36—H36126.7
C4—C5—H5126.5C36—C37—C38107.1 (7)
C6—C5—H5126.5C36—C37—Fe270.0 (4)
N2—C6—C5112.2 (5)C38—C37—Fe269.5 (4)
N2—C6—C7119.2 (6)C36—C37—H37126.4
C5—C6—C7128.6 (6)C38—C37—H37126.4
C11—C7—C8107.2 (5)Fe2—C37—H37125.7
C11—C7—C6127.2 (6)C34—C38—C37107.2 (6)
C8—C7—C6125.6 (6)C34—C38—C39127.4 (7)
C11—C7—Fe168.8 (3)C37—C38—C39125.3 (6)
C8—C7—Fe169.7 (3)C34—C38—Fe269.3 (4)
C6—C7—Fe1124.8 (4)C37—C38—Fe269.5 (4)
C9—C8—C7108.1 (5)C39—C38—Fe2128.3 (4)
C9—C8—Fe169.6 (3)N8—C39—C40111.9 (6)
C7—C8—Fe169.5 (3)N8—C39—C38120.4 (6)
C9—C8—H8125.9C40—C39—C38127.7 (7)
C7—C8—H8125.9C41—C40—C39105.6 (6)
Fe1—C8—H8126.6C41—C40—H40127.2
C8—C9—C10107.8 (6)C39—C40—H40127.2
C8—C9—Fe170.0 (3)C40—C41—N7106.8 (6)
C10—C9—Fe169.6 (4)C40—C41—C42129.1 (7)
C8—C9—H9126.1N7—C41—C42124.1 (6)
C10—C9—H9126.1C41—C42—H42A109.5
Fe1—C9—H9125.9C41—C42—H42B109.5
C11—C10—C9107.6 (6)H42A—C42—H42B109.5
C11—C10—Fe168.8 (4)C41—C42—H42C109.5
C9—C10—Fe169.9 (4)H42A—C42—H42C109.5
C11—C10—H10126.2H42B—C42—H42C109.5
C9—C10—H10126.2C44—C43—H43A109.5
Fe1—C10—H10126.6C44—C43—H43B109.5
C7—C11—C10109.3 (6)H43A—C43—H43B109.5
C7—C11—Fe171.0 (3)C44—C43—H43C109.5
C10—C11—Fe170.5 (4)H43A—C43—H43C109.5
C7—C11—H11125.3H43B—C43—H43C109.5
C10—C11—H11125.3O4—C44—N7119.1 (7)
Fe1—C11—H11124.8O4—C44—C43123.3 (7)
C13—C12—C16108.2 (6)N7—C44—C43117.6 (6)
C13—C12—Fe169.6 (3)C11—Fe1—C15105.8 (3)
C16—C12—Fe170.4 (3)C11—Fe1—C13157.5 (3)
C13—C12—H12125.9C15—Fe1—C1368.3 (3)
C16—C12—H12125.9C11—Fe1—C14120.6 (3)
Fe1—C12—H12125.7C15—Fe1—C1440.8 (2)
C12—C13—C14108.1 (6)C13—Fe1—C1440.9 (2)
C12—C13—Fe170.0 (3)C11—Fe1—C12159.4 (3)
C14—C13—Fe169.7 (4)C15—Fe1—C1267.8 (3)
C12—C13—H13125.9C13—Fe1—C1240.4 (2)
C14—C13—H13125.9C14—Fe1—C1268.4 (3)
Fe1—C13—H13125.9C11—Fe1—C1040.6 (2)
C15—C14—C13106.9 (6)C15—Fe1—C10120.7 (3)
C15—C14—Fe169.5 (4)C13—Fe1—C10122.2 (3)
C13—C14—Fe169.4 (4)C14—Fe1—C10105.1 (3)
C15—C14—H14126.5C12—Fe1—C10159.6 (3)
C13—C14—H14126.5C11—Fe1—C968.3 (3)
Fe1—C14—H14126.2C15—Fe1—C9157.1 (3)
C16—C15—C14108.6 (6)C13—Fe1—C9108.2 (3)
C16—C15—Fe170.7 (4)C14—Fe1—C9121.6 (3)
C14—C15—Fe169.7 (4)C12—Fe1—C9125.1 (3)
C16—C15—H15125.7C10—Fe1—C940.6 (2)
C14—C15—H15125.7C11—Fe1—C740.3 (2)
Fe1—C15—H15125.5C15—Fe1—C7122.2 (3)
C15—C16—C12108.1 (5)C13—Fe1—C7161.1 (3)
C15—C16—C17126.4 (6)C14—Fe1—C7157.1 (3)
C12—C16—C17125.5 (6)C12—Fe1—C7125.2 (2)
C15—C16—Fe169.3 (4)C10—Fe1—C768.2 (2)
C12—C16—Fe169.3 (3)C9—Fe1—C768.4 (2)
C17—C16—Fe1128.7 (4)C11—Fe1—C868.0 (2)
N4—C17—C18112.1 (6)C15—Fe1—C8159.8 (2)
N4—C17—C16120.6 (6)C13—Fe1—C8124.7 (3)
C18—C17—C16127.2 (6)C14—Fe1—C8159.0 (3)
C19—C18—C17106.6 (6)C12—Fe1—C8110.8 (2)
C19—C18—H18126.7C10—Fe1—C868.0 (3)
C17—C18—H18126.7C9—Fe1—C840.4 (2)
C18—C19—N3105.1 (5)C7—Fe1—C840.8 (2)
C18—C19—C20129.4 (6)C11—Fe1—C16122.4 (3)
N3—C19—C20125.4 (6)C15—Fe1—C1640.0 (2)
C19—C20—H20A109.5C13—Fe1—C1667.9 (2)
C19—C20—H20B109.5C14—Fe1—C1668.1 (3)
H20A—C20—H20B109.5C12—Fe1—C1640.3 (2)
C19—C20—H20C109.5C10—Fe1—C16157.1 (3)
H20A—C20—H20C109.5C9—Fe1—C16161.6 (3)
H20B—C20—H20C109.5C7—Fe1—C16109.0 (2)
C22—C21—H21A109.5C8—Fe1—C16125.8 (2)
C22—C21—H21B109.5C31—Fe2—C3367.8 (3)
H21A—C21—H21B109.5C31—Fe2—C34126.4 (3)
C22—C21—H21C109.5C33—Fe2—C34155.6 (2)
H21A—C21—H21C109.5C31—Fe2—C35107.9 (3)
H21B—C21—H21C109.5C33—Fe2—C35162.1 (3)
O2—C22—N3117.7 (7)C34—Fe2—C3540.8 (3)
O2—C22—C21124.8 (6)C31—Fe2—C3040.7 (2)
N3—C22—C21117.6 (6)C33—Fe2—C3068.2 (3)
C24—C23—H23A109.5C34—Fe2—C30108.4 (3)
C24—C23—H23B109.5C35—Fe2—C30120.8 (3)
H23A—C23—H23B109.5C31—Fe2—C38163.9 (3)
C24—C23—H23C109.5C33—Fe2—C38120.7 (3)
H23A—C23—H23C109.5C34—Fe2—C3840.6 (3)
H23B—C23—H23C109.5C35—Fe2—C3868.2 (3)
O3—C24—N5119.9 (6)C30—Fe2—C38126.7 (3)
O3—C24—C23124.1 (6)C31—Fe2—C37153.5 (3)
N5—C24—C23116.0 (6)C33—Fe2—C37107.9 (3)
C26—C25—H25A109.5C34—Fe2—C3768.4 (3)
C26—C25—H25B109.5C35—Fe2—C3767.6 (3)
H25A—C25—H25B109.5C30—Fe2—C37164.3 (3)
C26—C25—H25C109.5C38—Fe2—C3741.0 (3)
H25A—C25—H25C109.5C31—Fe2—C2968.6 (2)
H25B—C25—H25C109.5C33—Fe2—C2940.9 (2)
C26—C25—H25D109.5C34—Fe2—C29120.6 (3)
H25A—C25—H25D141.1C35—Fe2—C29155.6 (3)
H25B—C25—H25D56.3C30—Fe2—C2940.8 (2)
H25C—C25—H25D56.3C38—Fe2—C29108.1 (2)
C26—C25—H25E109.5C37—Fe2—C29126.4 (3)
H25A—C25—H25E56.3C31—Fe2—C3239.8 (2)
H25B—C25—H25E141.1C33—Fe2—C3240.5 (2)
H25C—C25—H25E56.3C34—Fe2—C32162.6 (3)
H25D—C25—H25E109.5C35—Fe2—C32125.2 (3)
C26—C25—H25F109.5C30—Fe2—C3267.8 (3)
H25A—C25—H25F56.3C38—Fe2—C32155.2 (3)
H25B—C25—H25F56.3C37—Fe2—C32119.8 (3)
H25C—C25—H25F141.1C29—Fe2—C3268.5 (2)
H25D—C25—H25F109.5C31—Fe2—C36119.4 (3)
H25E—C25—H25F109.5C33—Fe2—C36126.3 (3)
C27—C26—N5106.0 (5)C34—Fe2—C3667.6 (3)
C27—C26—C25129.5 (6)C35—Fe2—C3639.2 (3)
N5—C26—C25124.5 (5)C30—Fe2—C36154.0 (3)
C26—C27—C28106.1 (6)C38—Fe2—C3668.2 (3)
C26—C27—H27126.9C37—Fe2—C3640.6 (3)
C28—C27—H27126.9C29—Fe2—C36163.9 (3)
N6—C28—C27111.9 (5)C32—Fe2—C36107.8 (3)
N6—C28—C29120.5 (5)C4—N1—N2112.9 (5)
C27—C28—C29127.7 (6)C4—N1—C2129.0 (6)
C33—C29—C30106.6 (5)N2—N1—C2118.1 (6)
C33—C29—C28126.5 (5)C6—N2—N1102.8 (5)
C30—C29—C28126.9 (6)C19—N3—N4113.1 (5)
C33—C29—Fe269.0 (3)C19—N3—C22128.3 (5)
C30—C29—Fe269.4 (3)N4—N3—C22118.5 (6)
C28—C29—Fe2125.5 (4)C17—N4—N3103.1 (5)
C31—C30—C29107.9 (6)N6—N5—C26111.8 (5)
C31—C30—Fe269.2 (3)N6—N5—C24119.0 (5)
C29—C30—Fe269.8 (3)C26—N5—C24129.1 (5)
C31—C30—H30126.1C28—N6—N5104.2 (5)
C29—C30—H30126.1C41—N7—N8111.7 (5)
Fe2—C30—H30126.6C41—N7—C44130.1 (6)
C32—C31—C30108.9 (5)N8—N7—C44118.3 (6)
C32—C31—Fe270.8 (4)C39—N8—N7104.0 (5)
N1—C4—C5—C60.2 (7)C7—C8—Fe1—C14156.2 (7)
C3—C4—C5—C6178.9 (6)C9—C8—Fe1—C12120.2 (4)
C4—C5—C6—N20.8 (7)C7—C8—Fe1—C12120.2 (4)
C4—C5—C6—C7179.3 (6)C9—C8—Fe1—C1037.9 (4)
N2—C6—C7—C113.2 (9)C7—C8—Fe1—C1081.7 (4)
C5—C6—C7—C11176.6 (6)C7—C8—Fe1—C9119.6 (5)
N2—C6—C7—C8174.1 (5)C9—C8—Fe1—C7119.6 (5)
C5—C6—C7—C86.1 (10)C9—C8—Fe1—C16163.1 (4)
N2—C6—C7—Fe185.3 (7)C7—C8—Fe1—C1677.3 (4)
C5—C6—C7—Fe194.8 (7)C15—C16—Fe1—C1175.3 (4)
C11—C7—C8—C90.2 (7)C12—C16—Fe1—C11164.9 (4)
C6—C7—C8—C9178.0 (5)C17—C16—Fe1—C1145.3 (7)
Fe1—C7—C8—C959.0 (4)C12—C16—Fe1—C15119.8 (5)
C11—C7—C8—Fe158.8 (4)C17—C16—Fe1—C15120.6 (8)
C6—C7—C8—Fe1119.0 (6)C15—C16—Fe1—C1382.1 (4)
C7—C8—C9—C100.5 (7)C12—C16—Fe1—C1337.7 (4)
Fe1—C8—C9—C1059.5 (5)C17—C16—Fe1—C13157.3 (7)
C7—C8—C9—Fe159.0 (4)C15—C16—Fe1—C1437.9 (4)
C8—C9—C10—C111.1 (8)C12—C16—Fe1—C1481.9 (4)
Fe1—C9—C10—C1158.7 (5)C17—C16—Fe1—C14158.5 (7)
C8—C9—C10—Fe159.8 (4)C15—C16—Fe1—C12119.8 (5)
C8—C7—C11—C100.9 (7)C17—C16—Fe1—C12119.6 (7)
C6—C7—C11—C10178.6 (6)C15—C16—Fe1—C1038.9 (8)
Fe1—C7—C11—C1060.3 (5)C12—C16—Fe1—C10158.7 (6)
C8—C7—C11—Fe159.4 (4)C17—C16—Fe1—C1081.7 (9)
C6—C7—C11—Fe1118.3 (6)C15—C16—Fe1—C9163.3 (7)
C9—C10—C11—C71.3 (8)C12—C16—Fe1—C943.5 (9)
Fe1—C10—C11—C760.6 (4)C17—C16—Fe1—C976.1 (10)
C9—C10—C11—Fe159.3 (5)C15—C16—Fe1—C7117.8 (4)
C16—C12—C13—C140.5 (7)C12—C16—Fe1—C7122.3 (4)
Fe1—C12—C13—C1459.5 (5)C17—C16—Fe1—C72.8 (6)
C16—C12—C13—Fe160.0 (4)C15—C16—Fe1—C8160.2 (4)
C12—C13—C14—C150.1 (8)C12—C16—Fe1—C880.0 (4)
Fe1—C13—C14—C1559.6 (5)C17—C16—Fe1—C839.6 (7)
C12—C13—C14—Fe159.7 (4)C32—C31—Fe2—C3337.6 (4)
C13—C14—C15—C160.7 (8)C30—C31—Fe2—C3381.8 (4)
Fe1—C14—C15—C1660.2 (5)C32—C31—Fe2—C34165.3 (4)
C13—C14—C15—Fe159.6 (5)C30—C31—Fe2—C3475.3 (5)
C14—C15—C16—C121.0 (7)C32—C31—Fe2—C35123.9 (4)
Fe1—C15—C16—C1258.6 (4)C30—C31—Fe2—C35116.7 (4)
C14—C15—C16—C17176.9 (6)C32—C31—Fe2—C30119.4 (5)
Fe1—C15—C16—C17123.5 (6)C32—C31—Fe2—C38162.9 (8)
C14—C15—C16—Fe159.6 (5)C30—C31—Fe2—C3843.5 (11)
C13—C12—C16—C151.0 (7)C32—C31—Fe2—C3748.3 (8)
Fe1—C12—C16—C1558.6 (4)C30—C31—Fe2—C37167.7 (6)
C13—C12—C16—C17177.0 (5)C32—C31—Fe2—C2981.7 (4)
Fe1—C12—C16—C17123.5 (6)C30—C31—Fe2—C2937.7 (4)
C13—C12—C16—Fe159.6 (4)C30—C31—Fe2—C32119.4 (5)
C15—C16—C17—N46.6 (10)C32—C31—Fe2—C3682.7 (5)
C12—C16—C17—N4170.9 (6)C30—C31—Fe2—C36157.9 (5)
Fe1—C16—C17—N498.2 (7)C32—C33—Fe2—C3136.9 (4)
C15—C16—C17—C18177.7 (6)C29—C33—Fe2—C3182.4 (4)
C12—C16—C17—C184.8 (10)C32—C33—Fe2—C34167.6 (6)
Fe1—C16—C17—C1886.1 (8)C29—C33—Fe2—C3448.3 (8)
N4—C17—C18—C190.6 (7)C32—C33—Fe2—C3542.6 (11)
C16—C17—C18—C19176.6 (6)C29—C33—Fe2—C35161.9 (8)
C17—C18—C19—N30.1 (6)C32—C33—Fe2—C3081.0 (4)
C17—C18—C19—C20178.8 (6)C29—C33—Fe2—C3038.4 (3)
N5—C26—C27—C280.4 (7)C32—C33—Fe2—C38158.3 (4)
C25—C26—C27—C28179.4 (6)C29—C33—Fe2—C3882.3 (4)
C26—C27—C28—N60.1 (7)C32—C33—Fe2—C37115.2 (4)
C26—C27—C28—C29179.0 (6)C29—C33—Fe2—C37125.4 (4)
N6—C28—C29—C33174.9 (6)C32—C33—Fe2—C29119.3 (5)
C27—C28—C29—C334.2 (10)C29—C33—Fe2—C32119.3 (5)
N6—C28—C29—C303.6 (9)C32—C33—Fe2—C3674.1 (5)
C27—C28—C29—C30177.3 (6)C29—C33—Fe2—C36166.6 (4)
N6—C28—C29—Fe286.1 (7)C38—C34—Fe2—C31167.0 (4)
C27—C28—C29—Fe292.9 (7)C35—C34—Fe2—C3174.4 (6)
C33—C29—C30—C310.4 (7)C38—C34—Fe2—C3347.7 (9)
C28—C29—C30—C31178.4 (5)C35—C34—Fe2—C33166.3 (6)
Fe2—C29—C30—C3158.9 (4)C38—C34—Fe2—C35118.6 (7)
C33—C29—C30—Fe259.2 (4)C38—C34—Fe2—C30125.3 (4)
C28—C29—C30—Fe2119.6 (6)C35—C34—Fe2—C30116.0 (5)
C29—C30—C31—C321.1 (7)C35—C34—Fe2—C38118.6 (7)
Fe2—C30—C31—C3260.4 (5)C38—C34—Fe2—C3738.3 (4)
C29—C30—C31—Fe259.3 (4)C35—C34—Fe2—C3780.3 (5)
C30—C31—C32—C331.5 (8)C38—C34—Fe2—C2982.3 (5)
Fe2—C31—C32—C3358.5 (5)C35—C34—Fe2—C29159.1 (4)
C30—C31—C32—Fe260.0 (4)C38—C34—Fe2—C32160.1 (8)
C31—C32—C33—C291.3 (8)C35—C34—Fe2—C3241.5 (12)
Fe2—C32—C33—C2960.0 (4)C38—C34—Fe2—C3682.2 (5)
C31—C32—C33—Fe258.7 (5)C35—C34—Fe2—C3636.4 (4)
C30—C29—C33—C320.5 (7)C36—C35—Fe2—C31114.8 (4)
C28—C29—C33—C32179.3 (6)C34—C35—Fe2—C31125.4 (5)
Fe2—C29—C33—C3260.1 (5)C36—C35—Fe2—C3341.7 (11)
C30—C29—C33—Fe259.5 (4)C34—C35—Fe2—C33161.5 (8)
C28—C29—C33—Fe2119.3 (6)C36—C35—Fe2—C34119.8 (6)
C38—C34—C35—C360.1 (8)C36—C35—Fe2—C30157.5 (4)
Fe2—C34—C35—C3660.2 (5)C34—C35—Fe2—C3082.7 (5)
C38—C34—C35—Fe260.1 (5)C36—C35—Fe2—C3881.8 (5)
C34—C35—C36—C370.6 (8)C34—C35—Fe2—C3838.0 (4)
Fe2—C35—C36—C3758.6 (5)C36—C35—Fe2—C3737.3 (4)
C34—C35—C36—Fe259.3 (5)C34—C35—Fe2—C3782.4 (5)
C35—C36—C37—C380.9 (8)C36—C35—Fe2—C29167.7 (5)
Fe2—C36—C37—C3859.8 (5)C34—C35—Fe2—C2948.0 (8)
C35—C36—C37—Fe258.8 (5)C36—C35—Fe2—C3274.3 (5)
C35—C34—C38—C370.5 (7)C34—C35—Fe2—C32166.0 (4)
Fe2—C34—C38—C3759.4 (5)C34—C35—Fe2—C36119.8 (6)
C35—C34—C38—C39177.1 (6)C29—C30—Fe2—C31119.3 (5)
Fe2—C34—C38—C39123.1 (6)C31—C30—Fe2—C3380.9 (4)
C35—C34—C38—Fe259.9 (5)C29—C30—Fe2—C3338.4 (3)
C36—C37—C38—C340.9 (8)C31—C30—Fe2—C34124.8 (4)
Fe2—C37—C38—C3459.2 (4)C29—C30—Fe2—C34115.8 (4)
C36—C37—C38—C39176.8 (6)C31—C30—Fe2—C3581.8 (5)
Fe2—C37—C38—C39123.2 (6)C29—C30—Fe2—C35158.9 (4)
C36—C37—C38—Fe260.1 (5)C31—C30—Fe2—C38166.3 (4)
C34—C38—C39—N8177.1 (6)C29—C30—Fe2—C3874.4 (4)
C37—C38—C39—N80.1 (10)C31—C30—Fe2—C37159.5 (10)
Fe2—C38—C39—N890.8 (8)C29—C30—Fe2—C3740.1 (12)
C34—C38—C39—C401.7 (11)C31—C30—Fe2—C29119.3 (5)
C37—C38—C39—C40178.8 (6)C31—C30—Fe2—C3237.0 (4)
Fe2—C38—C39—C4090.5 (8)C29—C30—Fe2—C3282.3 (4)
N8—C39—C40—C411.1 (7)C31—C30—Fe2—C3648.4 (9)
C38—C39—C40—C41177.7 (6)C29—C30—Fe2—C36167.7 (7)
C39—C40—C41—N71.4 (7)C34—C38—Fe2—C3140.7 (11)
C39—C40—C41—C42177.6 (6)C37—C38—Fe2—C31159.4 (8)
C7—C11—Fe1—C15121.5 (4)C39—C38—Fe2—C3181.2 (12)
C10—C11—Fe1—C15118.9 (4)C34—C38—Fe2—C33159.2 (4)
C7—C11—Fe1—C13167.1 (6)C37—C38—Fe2—C3382.1 (4)
C10—C11—Fe1—C1347.6 (9)C39—C38—Fe2—C3337.2 (8)
C7—C11—Fe1—C14163.3 (4)C37—C38—Fe2—C34118.7 (6)
C10—C11—Fe1—C1477.2 (5)C39—C38—Fe2—C34121.9 (9)
C7—C11—Fe1—C1252.6 (9)C34—C38—Fe2—C3538.1 (5)
C10—C11—Fe1—C12172.1 (7)C37—C38—Fe2—C3580.5 (5)
C7—C11—Fe1—C10119.5 (6)C39—C38—Fe2—C35160.1 (8)
C7—C11—Fe1—C981.8 (4)C34—C38—Fe2—C3074.8 (5)
C10—C11—Fe1—C937.7 (4)C37—C38—Fe2—C30166.6 (4)
C10—C11—Fe1—C7119.5 (6)C39—C38—Fe2—C3047.2 (8)
C7—C11—Fe1—C838.1 (4)C34—C38—Fe2—C37118.7 (6)
C10—C11—Fe1—C881.4 (4)C39—C38—Fe2—C37119.4 (8)
C7—C11—Fe1—C1681.3 (4)C34—C38—Fe2—C29116.2 (4)
C10—C11—Fe1—C16159.2 (4)C37—C38—Fe2—C29125.1 (4)
C16—C15—Fe1—C11121.9 (4)C39—C38—Fe2—C295.8 (7)
C14—C15—Fe1—C11118.7 (4)C34—C38—Fe2—C32166.0 (6)
C16—C15—Fe1—C1381.0 (4)C37—C38—Fe2—C3247.3 (8)
C14—C15—Fe1—C1338.3 (4)C39—C38—Fe2—C3272.1 (10)
C16—C15—Fe1—C14119.4 (6)C34—C38—Fe2—C3680.5 (5)
C16—C15—Fe1—C1237.3 (4)C37—C38—Fe2—C3638.1 (5)
C14—C15—Fe1—C1282.1 (4)C39—C38—Fe2—C36157.5 (8)
C16—C15—Fe1—C10163.5 (4)C36—C37—Fe2—C3149.2 (9)
C14—C15—Fe1—C1077.2 (5)C38—C37—Fe2—C31167.4 (6)
C16—C15—Fe1—C9166.5 (6)C36—C37—Fe2—C33125.4 (5)
C14—C15—Fe1—C947.1 (9)C38—C37—Fe2—C33116.5 (4)
C16—C15—Fe1—C781.3 (4)C36—C37—Fe2—C3480.3 (5)
C14—C15—Fe1—C7159.3 (4)C38—C37—Fe2—C3437.9 (4)
C16—C15—Fe1—C852.9 (9)C36—C37—Fe2—C3536.2 (5)
C14—C15—Fe1—C8172.2 (7)C38—C37—Fe2—C3582.0 (5)
C14—C15—Fe1—C16119.4 (6)C36—C37—Fe2—C30161.6 (10)
C12—C13—Fe1—C11159.7 (6)C38—C37—Fe2—C3043.5 (13)
C14—C13—Fe1—C1140.6 (9)C36—C37—Fe2—C38118.2 (7)
C12—C13—Fe1—C1580.9 (4)C36—C37—Fe2—C29166.8 (5)
C14—C13—Fe1—C1538.3 (4)C38—C37—Fe2—C2975.0 (5)
C12—C13—Fe1—C14119.2 (6)C36—C37—Fe2—C3282.7 (6)
C14—C13—Fe1—C12119.2 (6)C38—C37—Fe2—C32159.2 (4)
C12—C13—Fe1—C10165.7 (4)C38—C37—Fe2—C36118.2 (7)
C14—C13—Fe1—C1075.2 (5)C33—C29—Fe2—C3180.4 (4)
C12—C13—Fe1—C9123.2 (4)C30—C29—Fe2—C3137.7 (4)
C14—C13—Fe1—C9117.6 (4)C28—C29—Fe2—C31159.0 (6)
C12—C13—Fe1—C746.7 (9)C30—C29—Fe2—C33118.1 (5)
C14—C13—Fe1—C7165.9 (7)C28—C29—Fe2—C33120.6 (6)
C12—C13—Fe1—C881.5 (4)C33—C29—Fe2—C34159.0 (4)
C14—C13—Fe1—C8159.3 (4)C30—C29—Fe2—C3482.9 (4)
C12—C13—Fe1—C1637.6 (4)C28—C29—Fe2—C3438.5 (6)
C14—C13—Fe1—C1681.6 (4)C33—C29—Fe2—C35166.7 (6)
C15—C14—Fe1—C1178.5 (5)C30—C29—Fe2—C3548.6 (7)
C13—C14—Fe1—C11163.2 (4)C28—C29—Fe2—C3572.8 (8)
C13—C14—Fe1—C15118.2 (6)C33—C29—Fe2—C30118.1 (5)
C15—C14—Fe1—C13118.2 (6)C28—C29—Fe2—C30121.4 (7)
C15—C14—Fe1—C1280.7 (4)C33—C29—Fe2—C38116.3 (4)
C13—C14—Fe1—C1237.5 (4)C30—C29—Fe2—C38125.6 (4)
C15—C14—Fe1—C10119.7 (4)C28—C29—Fe2—C384.3 (6)
C13—C14—Fe1—C10122.1 (4)C33—C29—Fe2—C3774.4 (5)
C15—C14—Fe1—C9160.5 (4)C30—C29—Fe2—C37167.5 (4)
C13—C14—Fe1—C981.3 (5)C28—C29—Fe2—C3746.1 (6)
C15—C14—Fe1—C750.0 (8)C33—C29—Fe2—C3237.5 (4)
C13—C14—Fe1—C7168.3 (5)C30—C29—Fe2—C3280.6 (4)
C15—C14—Fe1—C8172.5 (6)C28—C29—Fe2—C32158.1 (6)
C13—C14—Fe1—C854.3 (9)C33—C29—Fe2—C3642.3 (11)
C15—C14—Fe1—C1637.2 (4)C30—C29—Fe2—C36160.3 (9)
C13—C14—Fe1—C1681.1 (4)C28—C29—Fe2—C3678.3 (11)
C13—C12—Fe1—C11157.9 (7)C33—C32—Fe2—C31119.7 (6)
C16—C12—Fe1—C1138.8 (9)C31—C32—Fe2—C33119.7 (6)
C13—C12—Fe1—C1582.1 (4)C31—C32—Fe2—C3443.0 (11)
C16—C12—Fe1—C1537.0 (3)C33—C32—Fe2—C34162.8 (9)
C16—C12—Fe1—C13119.1 (5)C31—C32—Fe2—C3575.0 (5)
C13—C12—Fe1—C1437.9 (4)C33—C32—Fe2—C35165.3 (4)
C16—C12—Fe1—C1481.2 (4)C31—C32—Fe2—C3037.9 (4)
C13—C12—Fe1—C1037.0 (9)C33—C32—Fe2—C3081.9 (4)
C16—C12—Fe1—C10156.1 (7)C31—C32—Fe2—C38168.8 (5)
C13—C12—Fe1—C976.3 (5)C33—C32—Fe2—C3849.1 (8)
C16—C12—Fe1—C9164.6 (4)C31—C32—Fe2—C37157.4 (4)
C13—C12—Fe1—C7163.2 (4)C33—C32—Fe2—C3782.9 (4)
C16—C12—Fe1—C777.7 (4)C31—C32—Fe2—C2981.9 (4)
C13—C12—Fe1—C8119.6 (4)C33—C32—Fe2—C2937.8 (4)
C16—C12—Fe1—C8121.3 (4)C31—C32—Fe2—C36114.8 (4)
C13—C12—Fe1—C16119.1 (5)C33—C32—Fe2—C36125.5 (4)
C9—C10—Fe1—C11119.1 (6)C35—C36—Fe2—C3182.4 (5)
C11—C10—Fe1—C1578.3 (5)C37—C36—Fe2—C31157.2 (5)
C9—C10—Fe1—C15162.6 (4)C35—C36—Fe2—C33165.3 (4)
C11—C10—Fe1—C13160.5 (4)C37—C36—Fe2—C3374.3 (6)
C9—C10—Fe1—C1380.3 (5)C35—C36—Fe2—C3437.8 (4)
C11—C10—Fe1—C14119.6 (4)C37—C36—Fe2—C3482.5 (5)
C9—C10—Fe1—C14121.3 (4)C37—C36—Fe2—C35120.4 (7)
C11—C10—Fe1—C12172.0 (7)C35—C36—Fe2—C3048.4 (9)
C9—C10—Fe1—C1252.9 (9)C37—C36—Fe2—C30168.8 (6)
C11—C10—Fe1—C9119.1 (6)C35—C36—Fe2—C3881.8 (5)
C11—C10—Fe1—C737.3 (4)C37—C36—Fe2—C3838.6 (5)
C9—C10—Fe1—C781.9 (4)C35—C36—Fe2—C37120.4 (7)
C11—C10—Fe1—C881.4 (4)C35—C36—Fe2—C29161.6 (8)
C9—C10—Fe1—C837.8 (4)C37—C36—Fe2—C2941.2 (12)
C11—C10—Fe1—C1650.3 (8)C35—C36—Fe2—C32124.3 (4)
C9—C10—Fe1—C16169.4 (5)C37—C36—Fe2—C32115.4 (5)
C8—C9—Fe1—C1181.1 (4)C5—C4—N1—N20.5 (7)
C10—C9—Fe1—C1137.8 (4)C3—C4—N1—N2179.6 (5)
C8—C9—Fe1—C15160.3 (6)C5—C4—N1—C2178.8 (6)
C10—C9—Fe1—C1541.4 (8)C3—C4—N1—C20.3 (10)
C8—C9—Fe1—C13122.6 (4)O1—C2—N1—C45.4 (11)
C10—C9—Fe1—C13118.6 (4)C1—C2—N1—C4173.7 (6)
C8—C9—Fe1—C14165.5 (4)O1—C2—N1—N2173.9 (6)
C10—C9—Fe1—C1475.7 (5)C1—C2—N1—N27.0 (8)
C8—C9—Fe1—C1281.0 (4)C5—C6—N2—N11.0 (6)
C10—C9—Fe1—C12160.1 (4)C7—C6—N2—N1179.1 (5)
C8—C9—Fe1—C10118.9 (6)C4—N1—N2—C60.9 (6)
C8—C9—Fe1—C737.6 (4)C2—N1—N2—C6178.4 (5)
C10—C9—Fe1—C781.2 (4)C18—C19—N3—N40.4 (7)
C10—C9—Fe1—C8118.9 (6)C20—C19—N3—N4178.3 (5)
C8—C9—Fe1—C1648.0 (9)C18—C19—N3—C22175.7 (6)
C10—C9—Fe1—C16166.9 (7)C20—C19—N3—C223.1 (10)
C8—C7—Fe1—C11118.8 (5)O2—C22—N3—C191.6 (10)
C6—C7—Fe1—C11121.3 (7)C21—C22—N3—C19178.2 (6)
C11—C7—Fe1—C1575.8 (4)O2—C22—N3—N4176.7 (6)
C8—C7—Fe1—C15165.4 (4)C21—C22—N3—N43.1 (9)
C6—C7—Fe1—C1545.5 (6)C18—C17—N4—N30.8 (7)
C11—C7—Fe1—C13164.7 (7)C16—C17—N4—N3177.1 (5)
C8—C7—Fe1—C1345.9 (9)C19—N3—N4—C170.8 (7)
C6—C7—Fe1—C1374.0 (10)C22—N3—N4—C17176.6 (5)
C11—C7—Fe1—C1439.5 (8)C27—C26—N5—N60.5 (7)
C8—C7—Fe1—C14158.2 (6)C25—C26—N5—N6179.2 (5)
C6—C7—Fe1—C1481.9 (9)C27—C26—N5—C24175.6 (6)
C11—C7—Fe1—C12160.0 (4)C25—C26—N5—C244.1 (10)
C8—C7—Fe1—C1281.2 (4)O3—C24—N5—N6178.9 (5)
C6—C7—Fe1—C1238.7 (7)C23—C24—N5—N60.5 (8)
C11—C7—Fe1—C1037.6 (4)O3—C24—N5—C266.3 (10)
C8—C7—Fe1—C1081.2 (4)C23—C24—N5—C26174.3 (6)
C6—C7—Fe1—C10158.9 (6)C27—C28—N6—N50.2 (6)
C11—C7—Fe1—C981.4 (4)C29—C28—N6—N5179.4 (5)
C8—C7—Fe1—C937.3 (3)C26—N5—N6—C280.4 (6)
C6—C7—Fe1—C9157.2 (6)C24—N5—N6—C28176.1 (5)
C11—C7—Fe1—C8118.8 (5)C40—C41—N7—N81.4 (7)
C6—C7—Fe1—C8119.9 (7)C42—C41—N7—N8177.7 (6)
C11—C7—Fe1—C16118.0 (4)C40—C41—N7—C44177.7 (6)
C8—C7—Fe1—C16123.2 (4)C42—C41—N7—C443.2 (10)
C6—C7—Fe1—C163.3 (6)O4—C44—N7—C413.6 (11)
C9—C8—Fe1—C1181.9 (4)C43—C44—N7—C41178.0 (6)
C7—C8—Fe1—C1137.7 (3)O4—C44—N7—N8175.4 (6)
C9—C8—Fe1—C15157.7 (7)C43—C44—N7—N83.0 (9)
C7—C8—Fe1—C1538.1 (9)C40—C39—N8—N70.2 (7)
C9—C8—Fe1—C1376.9 (4)C38—C39—N8—N7178.7 (5)
C7—C8—Fe1—C13163.5 (3)C41—N7—N8—C390.7 (7)
C9—C8—Fe1—C1436.6 (9)C44—N7—N8—C39178.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O2i0.962.603.554 (8)175
C10—H10···O1ii0.932.573.490 (8)170
C14—H14···O2ii0.932.573.468 (8)164
C43—H43A···O3iii0.962.463.383 (9)161
C31—H31···O3ii0.932.593.515 (7)172
C36—H36···O4ii0.932.443.326 (8)159
Symmetry codes: (i) x+2, y+2, z+1; (ii) x1, y, z; (iii) x+5/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Fe(C11H11N2O)2]
Mr430.29
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)10.9021 (19), 12.7992 (16), 27.9421 (14)
β (°) 90.492 (16)
V3)3898.8 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.80
Crystal size (mm)0.22 × 0.18 × 0.11
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.832, 0.907
No. of measured, independent and
observed [I > 2σ(I)] reflections
8056, 7639, 4199
Rint0.032
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.077, 0.160, 1.07
No. of reflections7639
No. of parameters529
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.31, 0.34

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SIR2004 (Burla et al., 2005), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999), publCIF (Westrip, 2010).

 

Acknowledgements

The authors thank the Natural Science Foundation of China (No. 20572091) and the Natural Science Foundation of Jiangsu Province (No. 05KJB150151) for financial support.

References

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