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Acta Cryst. (2009). E65, m517    [ doi:10.1107/S1600536809012288 ]

2-Ferrocenyl-3-methoxy-6-methylpyridine

C. Xu, X.-Q. Hao, F. Liu, X.-J. Wu and M.-P. Song

Abstract top

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

Comment top

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

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

Related literature top

For historical background and for properties of ferrocenes and derivatives, see: Wang et al. (2008) and references cited therein. For the structure of (Z)-2,3-di(ferrocenyl)-2-butenedionate, see: Beletskaya et al. (2001). For cyclopalladated ferrocenyl–pyrimidine complexes, see: Xu et al. (2009). For the structure of {1-[(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-imino]ethyl}ferrocene, see: Hao et al. (2008). For the synthesis of functional compounds related to ferrocene-bearing units, see: Sarhan & Izumi (2003). Cg1 is the centroid of the Cp ring C8–C12.

Experimental top

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

Refinement 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: SMART (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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Partial view of the crystal packing showing the formation of the one-dimensional chain structure formed by the weak intermolecular C—H···N hydrogen bonding contacts.
2-Ferrocenyl-3-methoxy-6-methylpyridine top
Crystal data top
[Fe(C5H5)(C12H12NO)]F(000) = 640
Mr = 307.17Dx = 1.416 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3338 reflections
a = 5.9949 (13) Åθ = 2.7–26.2°
b = 20.284 (4) ŵ = 1.04 mm−1
c = 12.035 (2) ÅT = 294 K
β = 100.036 (3)°Block, red
V = 1441.0 (5) Å30.43 × 0.35 × 0.27 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2673 independent reflections
Radiation source: fine-focus sealed tube2280 reflections with I > 2σ(I)
graphiteRint = 0.020
φ and ω scansθmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −7→7
Tmin = 0.663, Tmax = 0.767k = −24→23
8219 measured reflectionsl = −14→10
Refinement 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) = 0.076H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0389P)2 + 0.3178P]
where P = (Fo2 + 2Fc2)/3
2673 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
[Fe(C5H5)(C12H12NO)]V = 1441.0 (5) Å3
Mr = 307.17Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.9949 (13) ŵ = 1.04 mm−1
b = 20.284 (4) ÅT = 294 K
c = 12.035 (2) Å0.43 × 0.35 × 0.27 mm
β = 100.036 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2673 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2280 reflections with I > 2σ(I)
Tmin = 0.663, Tmax = 0.767Rint = 0.020
8219 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.076Δρmax = 0.23 e Å−3
S = 1.06Δρmin = −0.27 e Å−3
2673 reflectionsAbsolute structure: ?
183 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
C10.2209 (3)0.19049 (9)0.27110 (15)0.0381 (4)
C20.3488 (4)0.20189 (10)0.37922 (17)0.0454 (5)
C30.2693 (4)0.24755 (11)0.44894 (18)0.0555 (6)
H30.35000.25630.52070.067*
C40.0683 (4)0.27974 (10)0.4098 (2)0.0576 (6)
H40.01370.31080.45520.069*
C5−0.0523 (4)0.26628 (9)0.30382 (18)0.0483 (5)
C6−0.2728 (4)0.29957 (11)0.2575 (2)0.0636 (6)
H6A−0.24990.33050.20020.095*
H6B−0.32770.32240.31720.095*
H6C−0.38180.26710.22550.095*
C70.6707 (4)0.17331 (14)0.5189 (2)0.0729 (7)
H7A0.71170.21870.53330.109*
H7B0.80540.14690.52630.109*
H7C0.57940.15870.57220.109*
C80.2889 (3)0.14341 (9)0.18926 (15)0.0375 (4)
C90.5096 (3)0.11890 (9)0.18035 (17)0.0416 (4)
H90.65210.13030.22980.050*
C100.4844 (4)0.07527 (9)0.08687 (17)0.0461 (5)
H100.60710.05100.06110.055*
C110.2523 (4)0.07186 (10)0.03813 (17)0.0477 (5)
H110.18680.0450−0.02710.057*
C120.1309 (3)0.11391 (9)0.10025 (16)0.0415 (4)
H12−0.03330.12100.08560.050*
C130.0699 (4)−0.01181 (13)0.2693 (2)0.0722 (8)
H13−0.0952−0.00680.25290.087*
C140.1998 (5)−0.05346 (11)0.2134 (2)0.0665 (7)
H140.1411−0.08190.14910.080*
C150.4275 (5)−0.04656 (11)0.2624 (3)0.0683 (7)
H150.5550−0.06960.23860.082*
C160.4429 (5)−0.00088 (13)0.3495 (2)0.0722 (8)
H160.58300.01320.39840.087*
C170.2229 (6)0.02140 (14)0.3562 (2)0.0769 (8)
H170.18200.05300.41090.092*
Fe10.29948 (4)0.042837 (12)0.20323 (2)0.03896 (11)
N10.0252 (3)0.22223 (7)0.23573 (14)0.0416 (4)
O10.5451 (3)0.16693 (8)0.40698 (12)0.0597 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0488 (11)0.0324 (9)0.0342 (10)−0.0068 (8)0.0100 (9)−0.0025 (8)
C20.0538 (12)0.0421 (10)0.0399 (11)−0.0080 (9)0.0073 (9)−0.0020 (9)
C30.0814 (16)0.0475 (12)0.0389 (12)−0.0181 (11)0.0144 (11)−0.0122 (10)
C40.0811 (17)0.0412 (11)0.0560 (14)−0.0047 (11)0.0269 (13)−0.0144 (10)
C50.0627 (13)0.0330 (10)0.0549 (13)−0.0036 (9)0.0255 (11)−0.0037 (9)
C60.0650 (15)0.0465 (13)0.0848 (18)0.0062 (11)0.0283 (13)−0.0044 (12)
C70.0755 (17)0.0905 (19)0.0452 (14)−0.0078 (14)−0.0108 (12)−0.0013 (13)
C80.0477 (10)0.0313 (9)0.0336 (10)0.0011 (7)0.0073 (8)0.0007 (7)
C90.0451 (10)0.0355 (10)0.0449 (12)−0.0024 (8)0.0096 (9)0.0001 (8)
C100.0565 (12)0.0390 (11)0.0456 (12)0.0068 (9)0.0166 (10)−0.0004 (9)
C110.0680 (14)0.0393 (10)0.0330 (11)0.0080 (9)0.0014 (10)−0.0046 (8)
C120.0491 (11)0.0379 (10)0.0345 (10)0.0061 (8)−0.0011 (8)0.0011 (8)
C130.0561 (14)0.0766 (17)0.085 (2)−0.0117 (13)0.0144 (14)0.0298 (15)
C140.0759 (17)0.0432 (12)0.0765 (19)−0.0133 (11)0.0025 (14)0.0082 (12)
C150.0702 (16)0.0464 (13)0.084 (2)0.0045 (11)0.0009 (14)0.0224 (13)
C160.0786 (18)0.0742 (17)0.0542 (16)−0.0149 (14)−0.0153 (13)0.0319 (14)
C170.127 (3)0.0601 (15)0.0502 (15)−0.0075 (16)0.0338 (16)0.0152 (12)
Fe10.04316 (17)0.03381 (16)0.03740 (18)−0.00120 (11)0.00003 (12)0.00266 (11)
N10.0508 (9)0.0325 (8)0.0433 (9)−0.0001 (7)0.0133 (8)−0.0012 (7)
O10.0649 (10)0.0689 (10)0.0398 (9)0.0010 (8)−0.0063 (7)−0.0086 (7)
Geometric parameters (Å, °) top
C1—N11.341 (2)C10—C111.415 (3)
C1—C21.410 (3)C10—Fe12.041 (2)
C1—C81.479 (2)C10—H100.9800
C2—O11.364 (3)C11—C121.416 (3)
C2—C31.389 (3)C11—Fe12.044 (2)
C3—C41.379 (3)C11—H110.9800
C3—H30.9300C12—Fe12.0492 (18)
C4—C51.379 (3)C12—H120.9800
C4—H40.9300C13—C141.399 (4)
C5—N11.349 (2)C13—C171.434 (4)
C5—C61.503 (3)C13—Fe12.034 (2)
C6—H6A0.9600C13—H130.9800
C6—H6B0.9600C14—C151.396 (4)
C6—H6C0.9600C14—Fe12.053 (2)
C7—O11.430 (3)C14—H140.9800
C7—H7A0.9600C15—C161.390 (4)
C7—H7B0.9600C15—Fe12.048 (2)
C7—H7C0.9600C15—H150.9800
C8—C121.431 (3)C16—C171.410 (4)
C8—C91.435 (3)C16—Fe12.024 (2)
C8—Fe12.0470 (18)C16—H160.9800
C9—C101.419 (3)C17—Fe12.021 (2)
C9—Fe12.0405 (18)C17—H170.9800
C9—H90.9800
N1—C1—C2121.29 (17)C13—C14—H14125.6
N1—C1—C8115.20 (16)Fe1—C14—H14125.6
C2—C1—C8123.50 (18)C16—C15—C14108.5 (3)
O1—C2—C3124.81 (19)C16—C15—Fe169.12 (13)
O1—C2—C1116.61 (17)C14—C15—Fe170.28 (13)
C3—C2—C1118.6 (2)C16—C15—H15125.8
C4—C3—C2118.7 (2)C14—C15—H15125.8
C4—C3—H3120.6Fe1—C15—H15125.8
C2—C3—H3120.6C15—C16—C17108.5 (2)
C3—C4—C5120.5 (2)C15—C16—Fe170.96 (14)
C3—C4—H4119.7C17—C16—Fe169.50 (13)
C5—C4—H4119.7C15—C16—H16125.8
N1—C5—C4120.8 (2)C17—C16—H16125.8
N1—C5—C6116.5 (2)Fe1—C16—H16125.8
C4—C5—C6122.67 (19)C16—C17—C13107.0 (3)
C5—C6—H6A109.5C16—C17—Fe169.70 (15)
C5—C6—H6B109.5C13—C17—Fe169.76 (14)
H6A—C6—H6B109.5C16—C17—H17126.5
C5—C6—H6C109.5C13—C17—H17126.5
H6A—C6—H6C109.5Fe1—C17—H17126.5
H6B—C6—H6C109.5C17—Fe1—C1640.81 (12)
O1—C7—H7A109.5C17—Fe1—C1341.42 (11)
O1—C7—H7B109.5C16—Fe1—C1368.62 (11)
H7A—C7—H7B109.5C17—Fe1—C10158.66 (12)
O1—C7—H7C109.5C16—Fe1—C10122.60 (10)
H7A—C7—H7C109.5C13—Fe1—C10158.36 (11)
H7B—C7—H7C109.5C17—Fe1—C9121.95 (11)
C12—C8—C9107.31 (16)C16—Fe1—C9105.66 (9)
C12—C8—C1123.04 (17)C13—Fe1—C9160.15 (11)
C9—C8—C1129.64 (17)C10—Fe1—C940.68 (8)
C12—C8—Fe169.63 (10)C17—Fe1—C11158.83 (12)
C9—C8—Fe169.20 (10)C16—Fe1—C11159.61 (11)
C1—C8—Fe1126.65 (13)C13—Fe1—C11123.25 (10)
C10—C9—C8107.66 (17)C10—Fe1—C1140.52 (8)
C10—C9—Fe169.66 (11)C9—Fe1—C1168.61 (8)
C8—C9—Fe169.69 (10)C17—Fe1—C8106.28 (10)
C10—C9—H9126.2C16—Fe1—C8120.70 (10)
C8—C9—H9126.2C13—Fe1—C8124.18 (10)
Fe1—C9—H9126.2C10—Fe1—C868.61 (7)
C11—C10—C9108.69 (17)C9—Fe1—C841.11 (7)
C11—C10—Fe169.88 (12)C11—Fe1—C868.66 (7)
C9—C10—Fe169.66 (11)C17—Fe1—C1567.90 (12)
C11—C10—H10125.7C16—Fe1—C1539.92 (11)
C9—C10—H10125.7C13—Fe1—C1567.65 (11)
Fe1—C10—H10125.7C10—Fe1—C15107.97 (10)
C10—C11—C12108.09 (17)C9—Fe1—C15120.91 (9)
C10—C11—Fe169.60 (11)C11—Fe1—C15124.95 (10)
C12—C11—Fe169.95 (11)C8—Fe1—C15156.28 (9)
C10—C11—H11126.0C17—Fe1—C12122.41 (11)
C12—C11—H11126.0C16—Fe1—C12157.56 (11)
Fe1—C11—H11126.0C13—Fe1—C12108.88 (9)
C11—C12—C8108.25 (17)C10—Fe1—C1268.15 (8)
C11—C12—Fe169.57 (11)C9—Fe1—C1268.74 (8)
C8—C12—Fe169.46 (10)C11—Fe1—C1240.48 (8)
C11—C12—H12125.9C8—Fe1—C1240.91 (7)
C8—C12—H12125.9C15—Fe1—C12161.55 (10)
Fe1—C12—H12125.9C17—Fe1—C1468.07 (12)
C14—C13—C17107.2 (2)C16—Fe1—C1467.38 (10)
C14—C13—Fe170.71 (14)C13—Fe1—C1440.03 (11)
C17—C13—Fe168.82 (14)C10—Fe1—C14123.10 (10)
C14—C13—H13126.4C9—Fe1—C14157.00 (10)
C17—C13—H13126.4C11—Fe1—C14109.84 (10)
Fe1—C13—H13126.4C8—Fe1—C14161.46 (10)
C15—C14—C13108.8 (2)C15—Fe1—C1439.82 (10)
C15—C14—Fe169.90 (13)C12—Fe1—C14125.97 (9)
C13—C14—Fe169.27 (13)C1—N1—C5120.02 (17)
C15—C14—H14125.6C2—O1—C7118.28 (18)
N1—C1—C2—O1179.85 (17)C9—C10—Fe1—C14−158.02 (13)
C8—C1—C2—O10.2 (3)C10—C9—Fe1—C17163.42 (14)
N1—C1—C2—C3−0.7 (3)C8—C9—Fe1—C17−77.75 (16)
C8—C1—C2—C3179.65 (18)C10—C9—Fe1—C16122.15 (15)
O1—C2—C3—C4179.62 (19)C8—C9—Fe1—C16−119.02 (14)
C1—C2—C3—C40.2 (3)C10—C9—Fe1—C13−167.6 (3)
C2—C3—C4—C50.6 (3)C8—C9—Fe1—C13−48.8 (3)
C3—C4—C5—N1−1.0 (3)C8—C9—Fe1—C10118.83 (16)
C3—C4—C5—C6179.5 (2)C10—C9—Fe1—C11−37.19 (12)
N1—C1—C8—C12−23.2 (3)C8—C9—Fe1—C1181.64 (12)
C2—C1—C8—C12156.51 (18)C10—C9—Fe1—C8−118.83 (16)
N1—C1—C8—C9156.33 (18)C10—C9—Fe1—C1581.66 (16)
C2—C1—C8—C9−24.0 (3)C8—C9—Fe1—C15−159.51 (13)
N1—C1—C8—Fe1−111.27 (17)C10—C9—Fe1—C12−80.79 (13)
C2—C1—C8—Fe168.4 (2)C8—C9—Fe1—C1238.04 (11)
C12—C8—C9—C100.1 (2)C10—C9—Fe1—C1453.4 (3)
C1—C8—C9—C10−179.48 (18)C8—C9—Fe1—C14172.2 (2)
Fe1—C8—C9—C1059.55 (13)C10—C11—Fe1—C17161.5 (3)
C12—C8—C9—Fe1−59.44 (13)C12—C11—Fe1—C1742.3 (3)
C1—C8—C9—Fe1121.0 (2)C10—C11—Fe1—C16−39.8 (3)
C8—C9—C10—C11−0.4 (2)C12—C11—Fe1—C16−159.1 (2)
Fe1—C9—C10—C1159.16 (14)C10—C11—Fe1—C13−160.67 (14)
C8—C9—C10—Fe1−59.57 (13)C12—C11—Fe1—C1380.10 (16)
C9—C10—C11—C120.6 (2)C12—C11—Fe1—C10−119.24 (17)
Fe1—C10—C11—C1259.58 (14)C10—C11—Fe1—C937.33 (11)
C9—C10—C11—Fe1−59.02 (14)C12—C11—Fe1—C9−81.91 (12)
C10—C11—C12—C8−0.5 (2)C10—C11—Fe1—C881.62 (12)
Fe1—C11—C12—C858.87 (13)C12—C11—Fe1—C8−37.61 (11)
C10—C11—C12—Fe1−59.36 (14)C10—C11—Fe1—C15−76.21 (15)
C9—C8—C12—C110.2 (2)C12—C11—Fe1—C15164.55 (13)
C1—C8—C12—C11179.86 (17)C10—C11—Fe1—C12119.24 (17)
Fe1—C8—C12—C11−58.94 (13)C10—C11—Fe1—C14−118.13 (13)
C9—C8—C12—Fe159.17 (13)C12—C11—Fe1—C14122.63 (14)
C1—C8—C12—Fe1−121.20 (17)C12—C8—Fe1—C17−121.03 (15)
C17—C13—C14—C15−0.5 (3)C9—C8—Fe1—C17120.25 (15)
Fe1—C13—C14—C1558.89 (17)C1—C8—Fe1—C17−4.4 (2)
C17—C13—C14—Fe1−59.40 (16)C12—C8—Fe1—C16−162.99 (14)
C13—C14—C15—C160.2 (3)C9—C8—Fe1—C1678.29 (15)
Fe1—C14—C15—C1658.73 (16)C1—C8—Fe1—C16−46.3 (2)
C13—C14—C15—Fe1−58.50 (17)C12—C8—Fe1—C13−79.27 (15)
C14—C15—C16—C170.2 (3)C9—C8—Fe1—C13162.01 (13)
Fe1—C15—C16—C1759.60 (16)C1—C8—Fe1—C1337.4 (2)
C14—C15—C16—Fe1−59.44 (17)C12—C8—Fe1—C1080.89 (13)
C15—C16—C17—C13−0.5 (3)C9—C8—Fe1—C10−37.83 (12)
Fe1—C16—C17—C1360.05 (17)C1—C8—Fe1—C10−162.45 (18)
C15—C16—C17—Fe1−60.51 (17)C12—C8—Fe1—C9118.72 (16)
C14—C13—C17—C160.6 (3)C1—C8—Fe1—C9−124.6 (2)
Fe1—C13—C17—C16−60.01 (16)C12—C8—Fe1—C1137.23 (12)
C14—C13—C17—Fe160.60 (17)C9—C8—Fe1—C11−81.49 (12)
C13—C17—Fe1—C16−118.0 (2)C1—C8—Fe1—C11153.89 (19)
C16—C17—Fe1—C13118.0 (2)C12—C8—Fe1—C15167.0 (2)
C16—C17—Fe1—C10−45.6 (3)C9—C8—Fe1—C1548.3 (3)
C13—C17—Fe1—C10−163.6 (2)C1—C8—Fe1—C15−76.3 (3)
C16—C17—Fe1—C9−76.37 (18)C9—C8—Fe1—C12−118.72 (16)
C13—C17—Fe1—C9165.62 (15)C1—C8—Fe1—C12116.7 (2)
C16—C17—Fe1—C11168.8 (2)C12—C8—Fe1—C14−51.7 (3)
C13—C17—Fe1—C1150.8 (3)C9—C8—Fe1—C14−170.4 (3)
C16—C17—Fe1—C8−118.39 (16)C1—C8—Fe1—C1465.0 (4)
C13—C17—Fe1—C8123.61 (16)C16—C15—Fe1—C17−38.02 (17)
C16—C17—Fe1—C1537.22 (16)C14—C15—Fe1—C1781.80 (19)
C13—C17—Fe1—C15−80.78 (17)C14—C15—Fe1—C16119.8 (3)
C16—C17—Fe1—C12−160.05 (15)C16—C15—Fe1—C13−82.94 (19)
C13—C17—Fe1—C1281.95 (18)C14—C15—Fe1—C1336.89 (18)
C16—C17—Fe1—C1480.32 (18)C16—C15—Fe1—C10119.66 (17)
C13—C17—Fe1—C14−37.68 (16)C14—C15—Fe1—C10−120.51 (17)
C15—C16—Fe1—C17119.2 (2)C16—C15—Fe1—C976.98 (19)
C15—C16—Fe1—C1380.30 (18)C14—C15—Fe1—C9−163.20 (16)
C17—C16—Fe1—C13−38.85 (17)C16—C15—Fe1—C11161.22 (16)
C15—C16—Fe1—C10−78.84 (18)C14—C15—Fe1—C11−78.9 (2)
C17—C16—Fe1—C10162.01 (15)C16—C15—Fe1—C842.1 (3)
C15—C16—Fe1—C9−119.76 (16)C14—C15—Fe1—C8161.9 (2)
C17—C16—Fe1—C9121.09 (16)C16—C15—Fe1—C12−165.7 (3)
C15—C16—Fe1—C11−49.2 (3)C14—C15—Fe1—C12−45.8 (4)
C17—C16—Fe1—C11−168.4 (2)C16—C15—Fe1—C14−119.8 (3)
C15—C16—Fe1—C8−161.72 (15)C11—C12—Fe1—C17−163.27 (15)
C17—C16—Fe1—C879.13 (18)C8—C12—Fe1—C1776.97 (16)
C17—C16—Fe1—C15−119.2 (2)C11—C12—Fe1—C16161.0 (2)
C15—C16—Fe1—C12168.2 (2)C8—C12—Fe1—C1641.2 (3)
C17—C16—Fe1—C1249.0 (3)C11—C12—Fe1—C13−119.46 (15)
C15—C16—Fe1—C1437.00 (17)C8—C12—Fe1—C13120.79 (14)
C17—C16—Fe1—C14−82.15 (18)C11—C12—Fe1—C1037.65 (12)
C14—C13—Fe1—C17−118.2 (2)C8—C12—Fe1—C10−82.10 (12)
C14—C13—Fe1—C16−79.86 (17)C11—C12—Fe1—C981.54 (13)
C17—C13—Fe1—C1638.29 (17)C8—C12—Fe1—C9−38.22 (11)
C14—C13—Fe1—C1045.7 (3)C8—C12—Fe1—C11−119.76 (17)
C17—C13—Fe1—C10163.9 (2)C11—C12—Fe1—C8119.76 (17)
C14—C13—Fe1—C9−156.5 (2)C11—C12—Fe1—C15−43.6 (4)
C17—C13—Fe1—C9−38.4 (3)C8—C12—Fe1—C15−163.4 (3)
C14—C13—Fe1—C1181.39 (17)C11—C12—Fe1—C14−78.20 (17)
C17—C13—Fe1—C11−160.45 (16)C8—C12—Fe1—C14162.04 (13)
C14—C13—Fe1—C8166.76 (14)C15—C14—Fe1—C17−81.35 (19)
C17—C13—Fe1—C8−75.09 (18)C13—C14—Fe1—C1738.96 (17)
C14—C13—Fe1—C15−36.71 (16)C15—C14—Fe1—C16−37.10 (18)
C17—C13—Fe1—C1581.45 (18)C13—C14—Fe1—C1683.22 (18)
C14—C13—Fe1—C12123.92 (15)C15—C14—Fe1—C13−120.3 (2)
C17—C13—Fe1—C12−117.93 (17)C15—C14—Fe1—C1078.06 (19)
C17—C13—Fe1—C14118.2 (2)C13—C14—Fe1—C10−161.63 (15)
C11—C10—Fe1—C17−161.7 (3)C15—C14—Fe1—C939.4 (3)
C9—C10—Fe1—C17−41.7 (3)C13—C14—Fe1—C9159.7 (2)
C11—C10—Fe1—C16164.63 (13)C15—C14—Fe1—C11121.21 (17)
C9—C10—Fe1—C16−75.38 (16)C13—C14—Fe1—C11−118.47 (16)
C11—C10—Fe1—C1348.7 (3)C15—C14—Fe1—C8−156.9 (3)
C9—C10—Fe1—C13168.6 (2)C13—C14—Fe1—C8−36.6 (4)
C11—C10—Fe1—C9−119.99 (16)C13—C14—Fe1—C15120.3 (2)
C9—C10—Fe1—C11119.99 (16)C15—C14—Fe1—C12163.71 (16)
C11—C10—Fe1—C8−81.77 (12)C13—C14—Fe1—C12−75.98 (18)
C9—C10—Fe1—C838.22 (11)C2—C1—N1—C50.3 (3)
C11—C10—Fe1—C15123.19 (13)C8—C1—N1—C5−179.98 (16)
C9—C10—Fe1—C15−116.83 (13)C4—C5—N1—C10.5 (3)
C11—C10—Fe1—C12−37.61 (11)C6—C5—N1—C1180.00 (17)
C9—C10—Fe1—C1282.37 (12)C3—C2—O1—C75.3 (3)
C11—C10—Fe1—C1481.99 (15)C1—C2—O1—C7−175.28 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N1i0.932.653.577 (3)172
C4—H4···Cg1ii0.932.963.880 (3)173
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N1i0.932.653.577 (3)172
C4—H4···Cg1ii0.932.963.880 (3)173
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z+1/2.
Acknowledgements top

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

references
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