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Acta Cryst. (2008). E64, m1275    [ doi:10.1107/S1600536808028973 ]

{1-[(3,5-Dimethyl-4H-1,2,4-triazol-4-yl)imino]ethyl}ferrocene

X.-Q. Hao, D.-S. Liang, R.-Y. Liu, J.-F. Gong and M.-P. Song

Abstract top

In the title compound, [Fe(C5H5)(C11H13N4)], the triazolyl and Cp ring form a dihedral angle of 76.6 (3)°. In the crystal structure, there are both intra- and intermolecular C-H...[pi] interactions, forming a one-dimensional chain structure along [010].

Comment top

During the past decades, we have systematically studied the cyclometallation reaction of Schiff base type of ferrocenylimines (Huo et al., 1994; Wu et al., 2001). Following these work, here we report the synthesis, characterization and crystal structure of the title ferrocenylimine ligand.

A view of the molecular structure of the title compound is given in Fig. 1. All the bond distances and angles are within normal ranges, the C11—N1 distance [1.290 (2) Å] is similar to those of the related complex (Hao et al., 2007) and the C11—N1—N2 angle is 115.15 (16)°. The triazolyl and Cp ring form a dihedral angle of 103.4 (3)°. Fig. 2 and Table 1 shows that in the crystal there exist intra- and intermolecular C—H···π interactions: H6···Cg1 = 2.519 Å [symmetry code for Cg1 (x, y, z), intra], and H5···Cg3 = 2.868 Å; symmetry code for Cg3 (x, -1/2 - y, -1/2 + z)]. Cg1 and Cg3 are the centroids of the triazolyl and one of the Cp rings C6–C10, respectively], which are attributed to construct the one-dimensional chain structure of the title compound. Partial stacking between neighbouring ferrocene units via inversion centres is shown in Fig. 3. The partial π–π stacking interactions are found between Cg2 and Cg2i [symmetry code i = (-x, -y, 2 - z)], with a distance 3.8525 (18) Å, the perpendicular distance is 3.295 Å with a slippage of 1.829 Å. Cg2 is the centroid of the Cp ring C1–C5.

Related literature top

For related literature, see: Hao et al. (2007); Huo et al. (1994); Wu et al. (2001). Cg1 and Cg3 are the centroids of the triazolyl ring and the Cp rings C6–C10, respectively.

Experimental top

Acetylferrocene (1 mmol) was dissolved in anhydrous toluene (40 ml) and 3,5-dimethyl-4-amino-4H-1,2,4-triazole (1.5 mmol) was added. The red solution was refluxed under argon atmosphere for about 3 days. Every day an addition of small quantities of activated Al2O3 was necessary to complete the reaction. The hot solution was carefully filtered, and the filtrate was concentrated to dryness in a rotary evaporator. The residue was purified by passing through a silica gel column with CH2Cl2 as eluent, giving the title compound, which was recrystallized from dichloromethane–petroleum ether solution at room temperature to give the desired product as colorless crystals suitable for single-crystal X-ray diffraction (yield 25%; m.p: 440 K-443 K). IR data (v_max/ cm-1): 1591, 1569, 1531, 1479, 1409, 1307, 1104, 1005, 827, 762. NMR δ(H) 4.87 (2H, s), 4.59 (2H, s), 4.25 (5H, s), 2.35 (6H, s), 2.07 (3H, s). MS-ESI+ [m/z]: 323 (M+H), 345 (M+Na), 667 (2M+Na).

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 Uiso(H) = 1.2Ueq(C) (1.5Ueq for methyl H).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. Partial view of the crystal packing showing the formation of the 1D chain structure formed by the C—H···π interactions.
[Figure 3] Fig. 3. Section of the crystal packing viewed down [100].
{1-[(3,5-Dimethyl-4H-1,2,4-triazol-4-yl)imino]ethyl}ferrocene top
Crystal data top
[Fe(C5H5)(C11H13N4)]F(000) = 672
Mr = 322.19Dx = 1.454 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.7851 (18) ÅCell parameters from 4008 reflections
b = 13.271 (3) Åθ = 2.5–26.1°
c = 13.035 (3) ŵ = 1.02 mm−1
β = 104.49 (3)°T = 293 K
V = 1471.4 (5) Å3Block, red
Z = 40.30 × 0.26 × 0.20 mm
Data collection top
Rigaku/MSC MODEL? CCD area-detector
diffractometer		2583 independent reflections
Radiation source: fine-focus sealed tube2485 reflections with I > 2σ(I)
graphiteRint = 0.026
φ and ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→10
Tmin = 0.749, Tmax = 0.822k = −15→15
14449 measured reflectionsl = −15→15
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.031P)2 + 0.6853P]
where P = (Fo2 + 2Fc2)/3
2583 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
[Fe(C5H5)(C11H13N4)]V = 1471.4 (5) Å3
Mr = 322.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.7851 (18) ŵ = 1.02 mm−1
b = 13.271 (3) ÅT = 293 K
c = 13.035 (3) Å0.30 × 0.26 × 0.20 mm
β = 104.49 (3)°
Data collection top
Rigaku/MSC MODEL? CCD area-detector
diffractometer		2583 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2485 reflections with I > 2σ(I)
Tmin = 0.749, Tmax = 0.822Rint = 0.026
14449 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.068Δρmax = 0.22 e Å−3
S = 1.09Δρmin = −0.18 e Å−3
2583 reflectionsAbsolute structure: ?
193 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Fe10.14717 (3)0.155436 (19)0.83336 (2)0.02657 (10)
N10.36589 (18)0.41476 (13)0.94499 (13)0.0366 (4)
N20.49929 (18)0.37952 (13)0.91279 (13)0.0351 (4)
N30.7280 (2)0.31235 (17)0.92302 (18)0.0566 (5)
N40.6890 (2)0.37255 (17)0.83286 (17)0.0538 (5)
C10.2665 (3)0.06374 (16)0.95248 (17)0.0456 (5)
H10.38110.05710.97630.055*
C20.1664 (3)0.00600 (16)0.87231 (18)0.0454 (5)
H20.1988−0.04800.83100.054*
C30.0112 (3)0.03956 (17)0.86285 (19)0.0482 (6)
H3−0.08340.01310.81350.058*
C40.0157 (3)0.11866 (18)0.93709 (19)0.0498 (6)
H4−0.07490.15620.94820.060*
C50.1738 (3)0.13290 (17)0.99218 (17)0.0469 (6)
H50.21270.18261.04820.056*
C60.3048 (2)0.23320 (14)0.77318 (15)0.0302 (4)
H60.41940.23050.79960.036*
C70.2125 (2)0.17029 (15)0.69381 (15)0.0346 (4)
H70.25230.11620.65640.042*
C80.0526 (2)0.19765 (16)0.67915 (15)0.0360 (5)
H8−0.03710.16550.63000.043*
C90.0439 (2)0.27709 (14)0.74964 (15)0.0324 (4)
H9−0.05280.31000.75680.039*
C100.2013 (2)0.30161 (13)0.80928 (14)0.0260 (4)
C110.2331 (2)0.37758 (14)0.89329 (14)0.0270 (4)
C120.0945 (2)0.42209 (15)0.92519 (16)0.0359 (4)
H12A0.13090.46720.98380.054*
H12B0.03380.36910.94570.054*
H12C0.03010.45850.86650.054*
C130.6131 (2)0.31904 (17)0.97039 (19)0.0440 (5)
C140.6040 (3)0.2679 (2)1.0694 (2)0.0640 (7)
H14A0.68140.21531.08540.096*
H14B0.50110.23941.06080.096*
H14C0.62360.31581.12640.096*
C150.5514 (2)0.41269 (16)0.82868 (17)0.0402 (5)
C160.4626 (3)0.48245 (19)0.7469 (2)0.0550 (6)
H16A0.52970.50610.70420.083*
H16B0.42640.53870.78060.083*
H16C0.37400.44780.70300.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02826 (16)0.02453 (16)0.02769 (16)−0.00021 (11)0.00847 (11)0.00028 (11)
N10.0289 (8)0.0381 (10)0.0449 (10)−0.0003 (7)0.0130 (7)−0.0112 (8)
N20.0232 (8)0.0385 (9)0.0442 (10)−0.0042 (7)0.0098 (7)−0.0095 (8)
N30.0298 (10)0.0669 (13)0.0758 (15)0.0070 (9)0.0181 (10)0.0068 (12)
N40.0339 (10)0.0674 (14)0.0661 (14)−0.0006 (9)0.0237 (9)0.0013 (11)
C10.0567 (14)0.0391 (12)0.0384 (12)0.0102 (10)0.0072 (10)0.0107 (10)
C20.0691 (15)0.0249 (10)0.0455 (12)0.0014 (10)0.0208 (11)0.0024 (9)
C30.0534 (14)0.0409 (12)0.0550 (14)−0.0139 (11)0.0223 (11)0.0045 (11)
C40.0596 (15)0.0439 (13)0.0588 (15)0.0053 (11)0.0393 (13)0.0130 (12)
C50.0758 (17)0.0389 (12)0.0298 (11)0.0017 (11)0.0202 (11)0.0021 (9)
C60.0281 (9)0.0323 (10)0.0325 (10)−0.0012 (8)0.0116 (8)−0.0007 (8)
C70.0439 (11)0.0349 (11)0.0274 (10)−0.0011 (9)0.0136 (9)−0.0021 (8)
C80.0378 (11)0.0371 (11)0.0284 (10)−0.0042 (9)−0.0006 (8)0.0025 (9)
C90.0277 (9)0.0308 (10)0.0362 (10)0.0014 (8)0.0033 (8)0.0055 (8)
C100.0249 (9)0.0247 (9)0.0295 (9)0.0008 (7)0.0088 (7)0.0040 (8)
C110.0262 (9)0.0251 (9)0.0315 (10)0.0002 (7)0.0104 (8)0.0034 (8)
C120.0314 (10)0.0386 (11)0.0397 (11)0.0054 (9)0.0125 (9)−0.0026 (9)
C130.0271 (10)0.0469 (13)0.0550 (14)−0.0032 (9)0.0050 (10)−0.0010 (11)
C140.0489 (14)0.0784 (19)0.0629 (16)0.0037 (13)0.0106 (12)0.0135 (15)
C150.0291 (10)0.0438 (12)0.0490 (12)−0.0102 (9)0.0122 (9)−0.0073 (10)
C160.0437 (13)0.0599 (15)0.0623 (15)−0.0071 (11)0.0150 (12)0.0090 (13)
Geometric parameters (Å, °) top
Fe1—C92.0310 (19)C4—H40.9800
Fe1—C62.0350 (19)C5—H50.9800
Fe1—C102.0402 (18)C6—C71.416 (3)
Fe1—C32.042 (2)C6—C101.444 (3)
Fe1—C22.044 (2)C6—H60.9800
Fe1—C12.044 (2)C7—C81.417 (3)
Fe1—C42.045 (2)C7—H70.9800
Fe1—C52.046 (2)C8—C91.413 (3)
Fe1—C72.0494 (19)C8—H80.9800
Fe1—C82.051 (2)C9—C101.444 (3)
N1—C111.290 (2)C9—H90.9800
N1—N21.419 (2)C10—C111.463 (3)
N2—C131.354 (3)C11—C121.503 (2)
N2—C151.363 (3)C12—H12A0.9600
N3—C131.311 (3)C12—H12B0.9600
N3—N41.391 (3)C12—H12C0.9600
N4—C151.310 (3)C13—C141.479 (3)
C1—C51.409 (3)C14—H14A0.9600
C1—C21.412 (3)C14—H14B0.9600
C1—H10.9800C14—H14C0.9600
C2—C31.410 (3)C15—C161.478 (3)
C2—H20.9800C16—H16A0.9600
C3—C41.421 (3)C16—H16B0.9600
C3—H30.9800C16—H16C0.9600
C4—C51.407 (4)
C9—Fe1—C669.23 (8)C5—C4—C3107.6 (2)
C9—Fe1—C1041.54 (7)C5—C4—Fe169.94 (12)
C6—Fe1—C1041.52 (7)C3—C4—Fe169.53 (12)
C9—Fe1—C3119.75 (9)C5—C4—H4126.2
C6—Fe1—C3160.23 (9)C3—C4—H4126.2
C10—Fe1—C3156.19 (9)Fe1—C4—H4126.2
C9—Fe1—C2154.55 (9)C4—C5—C1108.2 (2)
C6—Fe1—C2124.47 (9)C4—C5—Fe169.82 (13)
C10—Fe1—C2162.36 (9)C1—C5—Fe169.75 (12)
C3—Fe1—C240.38 (9)C4—C5—H5125.9
C9—Fe1—C1163.11 (9)C1—C5—H5125.9
C6—Fe1—C1109.00 (9)Fe1—C5—H5125.9
C10—Fe1—C1126.01 (9)C7—C6—C10108.47 (16)
C3—Fe1—C167.77 (10)C7—C6—Fe170.26 (11)
C2—Fe1—C140.41 (9)C10—C6—Fe169.43 (10)
C9—Fe1—C4107.15 (9)C7—C6—H6125.8
C6—Fe1—C4158.00 (9)C10—C6—H6125.8
C10—Fe1—C4121.37 (8)Fe1—C6—H6125.8
C3—Fe1—C440.71 (10)C6—C7—C8108.32 (17)
C2—Fe1—C468.24 (9)C6—C7—Fe169.17 (11)
C1—Fe1—C467.84 (10)C8—C7—Fe169.87 (11)
C9—Fe1—C5125.62 (9)C6—C7—H7125.8
C6—Fe1—C5123.19 (9)C8—C7—H7125.8
C10—Fe1—C5108.82 (8)Fe1—C7—H7125.8
C3—Fe1—C567.89 (10)C9—C8—C7108.47 (17)
C2—Fe1—C568.00 (9)C9—C8—Fe168.98 (11)
C1—Fe1—C540.30 (9)C7—C8—Fe169.71 (11)
C4—Fe1—C540.24 (10)C9—C8—H8125.8
C9—Fe1—C768.49 (8)C7—C8—H8125.8
C6—Fe1—C740.57 (8)Fe1—C8—H8125.8
C10—Fe1—C769.16 (8)C8—C9—C10108.53 (17)
C3—Fe1—C7123.13 (9)C8—C9—Fe170.53 (11)
C2—Fe1—C7106.84 (8)C10—C9—Fe169.57 (10)
C1—Fe1—C7121.81 (9)C8—C9—H9125.7
C4—Fe1—C7160.03 (10)C10—C9—H9125.7
C5—Fe1—C7157.74 (10)Fe1—C9—H9125.7
C9—Fe1—C840.50 (8)C9—C10—C6106.20 (16)
C6—Fe1—C868.38 (8)C9—C10—C11122.42 (16)
C10—Fe1—C869.05 (8)C6—C10—C11131.23 (16)
C3—Fe1—C8106.12 (9)C9—C10—Fe168.89 (10)
C2—Fe1—C8119.77 (9)C6—C10—Fe169.05 (10)
C1—Fe1—C8155.79 (9)C11—C10—Fe1123.25 (13)
C4—Fe1—C8123.78 (10)N1—C11—C10129.26 (17)
C5—Fe1—C8161.24 (9)N1—C11—C12113.23 (16)
C7—Fe1—C840.43 (8)C10—C11—C12117.50 (16)
C11—N1—N2115.15 (16)C11—C12—H12A109.5
C13—N2—C15106.71 (17)C11—C12—H12B109.5
C13—N2—N1125.56 (18)H12A—C12—H12B109.5
C15—N2—N1126.86 (17)C11—C12—H12C109.5
C13—N3—N4107.64 (18)H12A—C12—H12C109.5
C15—N4—N3107.37 (18)H12B—C12—H12C109.5
C5—C1—C2108.4 (2)N3—C13—N2109.1 (2)
C5—C1—Fe169.95 (12)N3—C13—C14126.6 (2)
C2—C1—Fe169.79 (12)N2—C13—C14124.2 (2)
C5—C1—H1125.8C13—C14—H14A109.5
C2—C1—H1125.8C13—C14—H14B109.5
Fe1—C1—H1125.8H14A—C14—H14B109.5
C3—C2—C1107.6 (2)C13—C14—H14C109.5
C3—C2—Fe169.74 (12)H14A—C14—H14C109.5
C1—C2—Fe169.80 (12)H14B—C14—H14C109.5
C3—C2—H2126.2N4—C15—N2109.1 (2)
C1—C2—H2126.2N4—C15—C16126.8 (2)
Fe1—C2—H2126.2N2—C15—C16124.03 (19)
C2—C3—C4108.2 (2)C15—C16—H16A109.5
C2—C3—Fe169.88 (12)C15—C16—H16B109.5
C4—C3—Fe169.76 (12)H16A—C16—H16B109.5
C2—C3—H3125.9C15—C16—H16C109.5
C4—C3—H3125.9H16A—C16—H16C109.5
Fe1—C3—H3125.9H16B—C16—H16C109.5
C11—N1—N2—C13−110.8 (2)C8—Fe1—C6—C1082.38 (12)
C11—N1—N2—C1581.3 (2)C10—C6—C7—C80.0 (2)
C13—N3—N4—C15−0.5 (3)Fe1—C6—C7—C859.08 (14)
C9—Fe1—C1—C538.3 (4)C10—C6—C7—Fe1−59.11 (13)
C6—Fe1—C1—C5119.29 (15)C9—Fe1—C7—C682.77 (12)
C10—Fe1—C1—C576.07 (17)C10—Fe1—C7—C638.07 (11)
C3—Fe1—C1—C5−81.56 (16)C3—Fe1—C7—C6−164.92 (12)
C2—Fe1—C1—C5−119.4 (2)C2—Fe1—C7—C6−123.76 (12)
C4—Fe1—C1—C5−37.43 (15)C1—Fe1—C7—C6−82.21 (14)
C7—Fe1—C1—C5162.25 (14)C4—Fe1—C7—C6163.8 (2)
C8—Fe1—C1—C5−161.34 (19)C5—Fe1—C7—C6−50.8 (3)
C9—Fe1—C1—C2157.8 (3)C8—Fe1—C7—C6119.84 (17)
C6—Fe1—C1—C2−121.27 (14)C9—Fe1—C7—C8−37.08 (12)
C10—Fe1—C1—C2−164.49 (12)C6—Fe1—C7—C8−119.84 (17)
C3—Fe1—C1—C237.87 (14)C10—Fe1—C7—C8−81.77 (12)
C4—Fe1—C1—C282.01 (15)C3—Fe1—C7—C875.24 (15)
C5—Fe1—C1—C2119.4 (2)C2—Fe1—C7—C8116.40 (13)
C7—Fe1—C1—C2−78.31 (16)C1—Fe1—C7—C8157.95 (12)
C8—Fe1—C1—C2−41.9 (3)C4—Fe1—C7—C843.9 (3)
C5—C1—C2—C3−0.2 (2)C5—Fe1—C7—C8−170.7 (2)
Fe1—C1—C2—C3−59.72 (15)C6—C7—C8—C9−0.4 (2)
C5—C1—C2—Fe159.54 (15)Fe1—C7—C8—C958.21 (14)
C9—Fe1—C2—C3−46.5 (3)C6—C7—C8—Fe1−58.65 (13)
C6—Fe1—C2—C3−162.68 (13)C6—Fe1—C8—C9−82.91 (12)
C10—Fe1—C2—C3164.2 (2)C10—Fe1—C8—C9−38.20 (11)
C1—Fe1—C2—C3118.7 (2)C3—Fe1—C8—C9117.18 (13)
C4—Fe1—C2—C337.77 (15)C2—Fe1—C8—C9158.75 (12)
C5—Fe1—C2—C381.29 (16)C1—Fe1—C8—C9−171.3 (2)
C7—Fe1—C2—C3−121.70 (14)C4—Fe1—C8—C976.29 (15)
C8—Fe1—C2—C3−79.70 (16)C5—Fe1—C8—C948.7 (3)
C9—Fe1—C2—C1−165.18 (18)C7—Fe1—C8—C9−120.27 (17)
C6—Fe1—C2—C178.62 (16)C9—Fe1—C8—C7120.27 (17)
C10—Fe1—C2—C145.5 (3)C6—Fe1—C8—C737.36 (11)
C3—Fe1—C2—C1−118.7 (2)C10—Fe1—C8—C782.06 (12)
C4—Fe1—C2—C1−80.92 (15)C3—Fe1—C8—C7−122.55 (13)
C5—Fe1—C2—C1−37.41 (14)C2—Fe1—C8—C7−80.99 (14)
C7—Fe1—C2—C1119.60 (14)C1—Fe1—C8—C7−51.1 (3)
C8—Fe1—C2—C1161.61 (13)C4—Fe1—C8—C7−163.44 (12)
C1—C2—C3—C40.3 (2)C5—Fe1—C8—C7169.0 (2)
Fe1—C2—C3—C4−59.46 (15)C7—C8—C9—C100.7 (2)
C1—C2—C3—Fe159.75 (15)Fe1—C8—C9—C1059.40 (13)
C9—Fe1—C3—C2158.96 (13)C7—C8—C9—Fe1−58.66 (14)
C6—Fe1—C3—C246.5 (3)C6—Fe1—C9—C880.65 (12)
C10—Fe1—C3—C2−168.23 (18)C10—Fe1—C9—C8119.43 (16)
C1—Fe1—C3—C2−37.90 (14)C3—Fe1—C9—C8−79.82 (14)
C4—Fe1—C3—C2−119.3 (2)C2—Fe1—C9—C8−47.1 (2)
C5—Fe1—C3—C2−81.58 (15)C1—Fe1—C9—C8167.7 (3)
C7—Fe1—C3—C276.51 (16)C4—Fe1—C9—C8−122.32 (13)
C8—Fe1—C3—C2117.25 (14)C5—Fe1—C9—C8−162.70 (13)
C9—Fe1—C3—C4−81.75 (16)C7—Fe1—C9—C837.01 (12)
C6—Fe1—C3—C4165.8 (2)C6—Fe1—C9—C10−38.79 (11)
C10—Fe1—C3—C4−48.9 (3)C3—Fe1—C9—C10160.74 (11)
C2—Fe1—C3—C4119.3 (2)C2—Fe1—C9—C10−166.50 (17)
C1—Fe1—C3—C481.39 (16)C1—Fe1—C9—C1048.3 (3)
C5—Fe1—C3—C437.71 (14)C4—Fe1—C9—C10118.25 (12)
C7—Fe1—C3—C4−164.21 (14)C5—Fe1—C9—C1077.86 (14)
C8—Fe1—C3—C4−123.46 (15)C7—Fe1—C9—C10−82.42 (12)
C2—C3—C4—C5−0.3 (2)C8—Fe1—C9—C10−119.43 (16)
Fe1—C3—C4—C5−59.83 (15)C8—C9—C10—C6−0.8 (2)
C2—C3—C4—Fe159.54 (15)Fe1—C9—C10—C659.25 (12)
C9—Fe1—C4—C5−125.37 (13)C8—C9—C10—C11−176.81 (17)
C6—Fe1—C4—C5−48.5 (3)Fe1—C9—C10—C11−116.81 (17)
C10—Fe1—C4—C5−82.20 (15)C8—C9—C10—Fe1−60.00 (13)
C3—Fe1—C4—C5118.7 (2)C7—C6—C10—C90.5 (2)
C2—Fe1—C4—C581.21 (14)Fe1—C6—C10—C9−59.14 (12)
C1—Fe1—C4—C537.49 (13)C7—C6—C10—C11176.06 (18)
C7—Fe1—C4—C5160.6 (2)Fe1—C6—C10—C11116.4 (2)
C8—Fe1—C4—C5−166.69 (13)C7—C6—C10—Fe159.63 (13)
C9—Fe1—C4—C3115.94 (15)C6—Fe1—C10—C9117.91 (15)
C6—Fe1—C4—C3−167.2 (2)C3—Fe1—C10—C9−45.2 (2)
C10—Fe1—C4—C3159.12 (13)C2—Fe1—C10—C9160.7 (2)
C2—Fe1—C4—C3−37.47 (14)C1—Fe1—C10—C9−164.44 (12)
C1—Fe1—C4—C3−81.20 (15)C4—Fe1—C10—C9−80.36 (14)
C5—Fe1—C4—C3−118.7 (2)C5—Fe1—C10—C9−122.90 (13)
C7—Fe1—C4—C341.9 (3)C7—Fe1—C10—C980.68 (12)
C8—Fe1—C4—C374.63 (17)C8—Fe1—C10—C937.27 (12)
C3—C4—C5—C10.2 (2)C9—Fe1—C10—C6−117.91 (15)
Fe1—C4—C5—C1−59.39 (15)C3—Fe1—C10—C6−163.1 (2)
C3—C4—C5—Fe159.57 (15)C2—Fe1—C10—C642.8 (3)
C2—C1—C5—C40.0 (2)C1—Fe1—C10—C677.64 (14)
Fe1—C1—C5—C459.44 (15)C4—Fe1—C10—C6161.73 (12)
C2—C1—C5—Fe1−59.44 (15)C5—Fe1—C10—C6119.19 (12)
C9—Fe1—C5—C473.43 (16)C7—Fe1—C10—C6−37.23 (11)
C6—Fe1—C5—C4160.41 (13)C8—Fe1—C10—C6−80.64 (12)
C10—Fe1—C5—C4116.66 (14)C9—Fe1—C10—C11115.73 (19)
C3—Fe1—C5—C4−38.14 (14)C6—Fe1—C10—C11−126.36 (19)
C2—Fe1—C5—C4−81.87 (15)C3—Fe1—C10—C1170.5 (3)
C1—Fe1—C5—C4−119.4 (2)C2—Fe1—C10—C11−83.6 (3)
C7—Fe1—C5—C4−162.5 (2)C1—Fe1—C10—C11−48.71 (18)
C8—Fe1—C5—C436.5 (3)C4—Fe1—C10—C1135.37 (18)
C9—Fe1—C5—C1−167.19 (13)C5—Fe1—C10—C11−7.17 (17)
C6—Fe1—C5—C1−80.21 (16)C7—Fe1—C10—C11−163.58 (17)
C10—Fe1—C5—C1−123.96 (14)C8—Fe1—C10—C11153.00 (16)
C3—Fe1—C5—C181.24 (15)N2—N1—C11—C102.6 (3)
C2—Fe1—C5—C137.51 (14)N2—N1—C11—C12−176.20 (16)
C4—Fe1—C5—C1119.4 (2)C9—C10—C11—N1−171.86 (19)
C7—Fe1—C5—C1−43.2 (3)C6—C10—C11—N113.2 (3)
C8—Fe1—C5—C1155.9 (2)Fe1—C10—C11—N1103.5 (2)
C9—Fe1—C6—C7−80.80 (12)C9—C10—C11—C126.9 (3)
C10—Fe1—C6—C7−119.61 (16)C6—C10—C11—C12−168.03 (18)
C3—Fe1—C6—C740.1 (3)Fe1—C10—C11—C12−77.7 (2)
C2—Fe1—C6—C774.84 (14)N4—N3—C13—N21.5 (3)
C1—Fe1—C6—C7117.07 (12)N4—N3—C13—C14−179.9 (2)
C4—Fe1—C6—C7−165.2 (2)C15—N2—C13—N3−1.8 (2)
C5—Fe1—C6—C7159.45 (12)N1—N2—C13—N3−171.75 (18)
C8—Fe1—C6—C7−37.23 (12)C15—N2—C13—C14179.5 (2)
C9—Fe1—C6—C1038.81 (11)N1—N2—C13—C149.5 (3)
C3—Fe1—C6—C10159.7 (2)N3—N4—C15—N2−0.6 (3)
C2—Fe1—C6—C10−165.55 (11)N3—N4—C15—C16179.7 (2)
C1—Fe1—C6—C10−123.32 (11)C13—N2—C15—N41.5 (2)
C4—Fe1—C6—C10−45.6 (3)N1—N2—C15—N4171.25 (18)
C5—Fe1—C6—C10−80.93 (13)C13—N2—C15—C16−178.9 (2)
C7—Fe1—C6—C10119.61 (16)N1—N2—C15—C16−9.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···Cg10.982.523.255 (3)132.
C5—H5···Cg3i0.982.873.703 (5)144.
Symmetry codes: (i) x, −y−1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···Cg10.982.523.255 (3)132.
C5—H5···Cg3i0.982.873.703 (5)144.
Symmetry codes: (i) x, −y−1/2, z−1/2.
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (No. 20572102), the Innovation Fund for Outstanding Scholar of Henan Province (No. 074200510005) and the Natural Science Foundation of Henan Province (No. 0524270054).

references
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