supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

hk2443 scheme

Acta Cryst. (2008). E64, m730    [ doi:10.1107/S1600536808008714 ]

2-Amino-4-(4-chlorophenyl)-6-ferrocenylpyridine-3-carbonitrile

J. Zhang, S. Yan, Z. He, L. Xu and S. Huang

Abstract top

In the molecule of the title compound, [Fe(C5H5)(C17H11ClN3)], the dihedral angles between the two five-membered rings and between the two six-membered rings are 3.28 (4) and 51.33 (4)°, respectively. In the crystal structure, intermolecular N-H...N hydrogen bonds link the molecules into centrosymmetric dimers.

Comment top

Metallocenes are known to exhibit a wide range of biological activity. Among them, ferrocene has attracted special attention since it is neutral, chemically stable, non-toxic and able to cross cell membranes (Dombrowski et al., 1986). In fact, it is now well established that the incorporation of ferrocene units into organic molecules introduces significant and new properties in these materials. In addition, it has been demonstrated that molecules containing cyanopyridine moiety may be able to work as ligands towards transition-metal ions (Alyoubi, 2000), new drugs (Murata et al., 2004; Desai & Shah, 2003) and significant intermediates for the synthesis of important vitamins such as nicotinic acids and nicotinamides. For these reasons, the synthesis of new compounds containing cyanopyridine derivatives is strongly desired. We report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), rings A (N1/C1-C5), B (C17-C22), C (C6-C10) and D (C11-C15) are, of course, planar. The dihedral angles between them are A/B = 51.33 (4)°, A/C = 13.20 (3)°, A/D = 16.32 (4)°, B/C = 46.38 (3)°, B/D= 44.47 (3)° and C/D = 3.28 (4)°. So, rings C and D are nearly paralllel to each other.

In the crystal structure, intermolecular N-H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Dombrowski et al. (1986); Alyoubi (2000); Desai & Shah (2003); Murata et al. (2004).

Experimental top

Compound (I) was prepared by the reaction of 4-chlorobenzaldehyde (2 mmol), malononitrile (2 mmol), acetylferrocene (2 mmol) and ammonium acetate (4 mmol) in water (2 ml). Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an aqueous ethanol solution (95%) (yield; 95%, m.p. 548-550 K). IR (cm-1): 3457, 3354, 2211; 1H NMR (DMSO-d6): 4.10 (5H, s, ferrocenyl), 4.50 (2H, s, ferrocenyl), 5.04 (2H, s, ferrocenyl), 6.81 (2H, brs, NH2), 6.95 (1H, s, ArH), 7.64 (2H, d, J = 8.4 Hz, ArH), 7.68 (2H, d, J = 8.4 Hz, ArH).7.87 (2H, brs, NH2), 7.88–8.01 (4H, m, ArH), 11.85 (1H, s, NH).

Refinement top

H atoms were positioned geometrically, with N-H = 0.86 Å (for NH2) and C-H = 0.93 Å for aromatic H,and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.
2-Amino-4-(4-chlorophenyl)-6-ferrocenylpyridine-3-carbonitrile top
Crystal data top
[Fe(C5H5)(C17H11ClN3)]F000 = 848
Mr = 413.68Dx = 1.482 Mg m−3
Monoclinic, P21/nMelting point = 548–550 K
Hall symbol: -P 2ynMo Kα radiation
λ = 0.71073 Å
a = 12.1517 (13) ÅCell parameters from 2405 reflections
b = 7.4214 (11) Åθ = 2.9–26.2º
c = 20.742 (2) ŵ = 0.97 mm−1
β = 97.691 (2)ºT = 298 (2) K
V = 1853.7 (4) Å3Block, red
Z = 40.20 × 0.15 × 0.09 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3260 independent reflections
Radiation source: fine-focus sealed tube2298 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.830, Tmax = 0.918k = −8→6
8876 measured reflectionsl = −24→24
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.093  w = 1/[σ2(Fo2) + (0.0178P)2 + 2.3504P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
3260 reflectionsΔρmax = 0.44 e Å−3
244 parametersΔρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Fe(C5H5)(C17H11ClN3)]V = 1853.7 (4) Å3
Mr = 413.68Z = 4
Monoclinic, P21/nMo Kα
a = 12.1517 (13) ŵ = 0.97 mm−1
b = 7.4214 (11) ÅT = 298 (2) K
c = 20.742 (2) Å0.20 × 0.15 × 0.09 mm
β = 97.691 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		3260 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2298 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 0.918Rint = 0.041
8876 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046244 parameters
wR(F2) = 0.093H-atom parameters constrained
S = 1.09Δρmax = 0.44 e Å−3
3260 reflectionsΔρmin = −0.43 e Å−3
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 > 2sigma(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
Fe10.38223 (4)0.42499 (7)0.10732 (3)0.03424 (16)
Cl10.81792 (10)1.44271 (17)0.38672 (6)0.0694 (4)
N10.3585 (2)0.5432 (4)0.27711 (13)0.0335 (7)
N20.3644 (2)0.4443 (4)0.38140 (14)0.0450 (8)
H2A0.31540.36490.36720.054*
H2B0.38920.44910.42220.054*
N30.5500 (3)0.6983 (5)0.48341 (17)0.0652 (12)
C10.4019 (3)0.5604 (5)0.33992 (16)0.0321 (8)
C20.4807 (3)0.6949 (5)0.36089 (16)0.0301 (8)
C30.5168 (3)0.8132 (5)0.31540 (17)0.0307 (8)
C40.4739 (3)0.7885 (5)0.25086 (17)0.0309 (8)
H40.49770.86130.21890.037*
C50.3950 (3)0.6543 (5)0.23368 (16)0.0292 (8)
C60.3441 (3)0.6283 (5)0.16610 (16)0.0287 (8)
C70.3802 (3)0.6998 (5)0.10848 (18)0.0366 (9)
H70.44080.77550.10700.044*
C80.3080 (3)0.6355 (5)0.05402 (17)0.0396 (10)
H80.31250.66170.01060.048*
C90.2277 (3)0.5243 (5)0.07769 (17)0.0390 (10)
H90.17010.46480.05230.047*
C100.2493 (3)0.5186 (5)0.14592 (17)0.0345 (9)
H100.20880.45430.17320.041*
C110.5039 (4)0.2760 (6)0.1590 (2)0.0615 (13)
H110.53850.30050.20080.074*
C120.5390 (3)0.3359 (6)0.1002 (2)0.0582 (13)
H120.60030.40810.09640.070*
C130.4640 (4)0.2662 (6)0.0484 (2)0.0562 (12)
H130.46720.28350.00420.067*
C140.3841 (4)0.1665 (6)0.0753 (3)0.0594 (13)
H140.32490.10570.05190.071*
C150.4071 (4)0.1726 (6)0.1426 (3)0.0648 (14)
H150.36580.11780.17170.078*
C160.5217 (3)0.7025 (5)0.42883 (19)0.0409 (10)
C170.5934 (3)0.9656 (5)0.33533 (17)0.0308 (8)
C180.5737 (3)1.0847 (6)0.38359 (19)0.0469 (10)
H180.51271.06630.40550.056*
C190.6424 (3)1.2308 (6)0.4002 (2)0.0489 (11)
H190.62761.30990.43280.059*
C200.7325 (3)1.2576 (5)0.36813 (19)0.0429 (10)
C210.7559 (3)1.1393 (6)0.3206 (2)0.0487 (11)
H210.81821.15670.29980.058*
C220.6861 (3)0.9946 (6)0.30423 (19)0.0450 (10)
H220.70150.91550.27180.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0363 (3)0.0281 (3)0.0382 (3)0.0077 (3)0.0046 (2)−0.0010 (3)
Cl10.0680 (7)0.0544 (8)0.0859 (9)−0.0359 (6)0.0103 (6)−0.0084 (7)
N10.0387 (16)0.0311 (18)0.0301 (15)−0.0057 (15)0.0022 (13)0.0036 (15)
N20.0533 (19)0.049 (2)0.0304 (16)−0.0262 (18)−0.0027 (14)0.0062 (18)
N30.085 (3)0.067 (3)0.039 (2)−0.033 (2)−0.0095 (19)0.010 (2)
C10.0330 (18)0.033 (2)0.0308 (19)−0.0026 (18)0.0045 (15)0.0014 (19)
C20.0306 (19)0.029 (2)0.0293 (19)−0.0047 (16)0.0005 (16)−0.0001 (17)
C30.0280 (18)0.027 (2)0.038 (2)−0.0002 (16)0.0048 (16)−0.0007 (17)
C40.0320 (19)0.029 (2)0.032 (2)−0.0036 (16)0.0054 (16)0.0039 (17)
C50.0295 (18)0.0260 (19)0.0326 (19)0.0050 (16)0.0056 (16)0.0004 (17)
C60.0323 (19)0.027 (2)0.0264 (18)0.0038 (16)0.0022 (15)0.0028 (16)
C70.042 (2)0.026 (2)0.042 (2)0.0062 (19)0.0067 (18)0.006 (2)
C80.050 (2)0.042 (2)0.0275 (19)0.011 (2)0.0043 (18)0.0011 (19)
C90.039 (2)0.040 (2)0.036 (2)0.0075 (18)−0.0011 (17)−0.0050 (19)
C100.0318 (19)0.035 (2)0.036 (2)0.0041 (17)0.0018 (16)−0.0006 (18)
C110.065 (3)0.054 (3)0.061 (3)0.031 (3)−0.008 (3)0.001 (3)
C120.039 (2)0.052 (3)0.084 (4)0.018 (2)0.006 (2)−0.009 (3)
C130.058 (3)0.049 (3)0.064 (3)0.014 (2)0.017 (2)−0.017 (3)
C140.065 (3)0.033 (3)0.079 (4)0.007 (2)0.006 (3)−0.011 (3)
C150.075 (3)0.038 (3)0.083 (4)0.017 (3)0.017 (3)0.015 (3)
C160.048 (2)0.036 (2)0.037 (2)−0.0157 (19)0.0013 (19)0.006 (2)
C170.0309 (18)0.026 (2)0.0358 (19)−0.0052 (16)0.0041 (15)0.0030 (17)
C180.043 (2)0.044 (2)0.057 (3)−0.014 (2)0.0189 (19)−0.012 (2)
C190.053 (3)0.040 (2)0.056 (3)−0.011 (2)0.013 (2)−0.012 (2)
C200.043 (2)0.039 (2)0.046 (2)−0.014 (2)0.0060 (19)0.000 (2)
C210.041 (2)0.049 (3)0.060 (3)−0.013 (2)0.019 (2)0.002 (2)
C220.045 (2)0.045 (2)0.046 (2)−0.008 (2)0.0123 (19)−0.004 (2)
Geometric parameters (Å, °) top
Fe1—C152.019 (5)C7—C81.417 (5)
Fe1—C102.020 (3)C7—H70.9300
Fe1—C142.031 (4)C8—C91.415 (5)
Fe1—C62.032 (3)C8—H80.9300
Fe1—C112.033 (4)C9—C101.405 (5)
Fe1—C92.034 (4)C9—H90.9300
Fe1—C72.040 (4)C10—H100.9300
Fe1—C122.040 (4)C11—C151.408 (6)
Fe1—C132.048 (4)C11—C121.415 (6)
Fe1—C82.052 (4)C11—H110.9300
Cl1—C201.734 (4)C12—C131.412 (6)
N1—C51.339 (4)C12—H120.9300
N1—C11.344 (4)C13—C141.395 (6)
N2—C11.340 (4)C13—H130.9300
N2—H2A0.8600C14—C151.385 (6)
N2—H2B0.8600C14—H140.9300
N3—C161.139 (4)C15—H150.9300
C1—C21.411 (5)C17—C181.380 (5)
C2—C31.401 (5)C17—C221.388 (5)
C2—C161.432 (5)C18—C191.384 (5)
C3—C41.382 (5)C18—H180.9300
C3—C171.488 (5)C19—C201.369 (5)
C4—C51.396 (5)C19—H190.9300
C4—H40.9300C20—C211.377 (5)
C5—C61.467 (4)C21—C221.383 (5)
C6—C101.426 (5)C21—H210.9300
C6—C71.429 (5)C22—H220.9300
C15—Fe1—C10105.34 (18)C6—C7—Fe169.2 (2)
C15—Fe1—C1440.01 (18)C8—C7—H7125.8
C10—Fe1—C14119.93 (18)C6—C7—H7125.8
C15—Fe1—C6120.45 (18)Fe1—C7—H7126.4
C10—Fe1—C641.22 (13)C9—C8—C7107.6 (3)
C14—Fe1—C6155.60 (18)C9—C8—Fe169.1 (2)
C15—Fe1—C1140.67 (18)C7—C8—Fe169.3 (2)
C10—Fe1—C11122.83 (18)C9—C8—H8126.2
C14—Fe1—C1167.62 (19)C7—C8—H8126.2
C6—Fe1—C11107.21 (16)Fe1—C8—H8127.0
C15—Fe1—C9122.21 (19)C10—C9—C8108.8 (3)
C10—Fe1—C940.55 (13)C10—C9—Fe169.2 (2)
C14—Fe1—C9107.10 (17)C8—C9—Fe170.4 (2)
C6—Fe1—C968.69 (14)C10—C9—H9125.6
C11—Fe1—C9158.94 (19)C8—C9—H9125.6
C15—Fe1—C7157.7 (2)Fe1—C9—H9126.4
C10—Fe1—C768.88 (15)C9—C10—C6108.3 (3)
C14—Fe1—C7161.62 (19)C9—C10—Fe170.3 (2)
C6—Fe1—C741.10 (13)C6—C10—Fe169.86 (19)
C11—Fe1—C7123.14 (18)C9—C10—H10125.9
C9—Fe1—C768.23 (15)C6—C10—H10125.9
C15—Fe1—C1268.25 (19)Fe1—C10—H10125.6
C10—Fe1—C12160.75 (17)C15—C11—C12107.5 (4)
C14—Fe1—C1267.58 (19)C15—C11—Fe169.1 (2)
C6—Fe1—C12125.06 (16)C12—C11—Fe169.9 (2)
C11—Fe1—C1240.67 (17)C15—C11—H11126.2
C9—Fe1—C12158.22 (17)C12—C11—H11126.2
C7—Fe1—C12109.75 (18)Fe1—C11—H11126.3
C15—Fe1—C1367.7 (2)C13—C12—C11107.6 (4)
C10—Fe1—C13155.78 (16)C13—C12—Fe170.1 (2)
C14—Fe1—C1340.00 (17)C11—C12—Fe169.4 (2)
C6—Fe1—C13162.41 (16)C13—C12—H12126.2
C11—Fe1—C1367.98 (19)C11—C12—H12126.2
C9—Fe1—C13122.00 (16)Fe1—C12—H12125.9
C7—Fe1—C13126.16 (18)C14—C13—C12107.5 (4)
C12—Fe1—C1340.39 (16)C14—C13—Fe169.3 (2)
C15—Fe1—C8159.28 (19)C12—C13—Fe169.5 (2)
C10—Fe1—C868.55 (15)C14—C13—H13126.2
C14—Fe1—C8124.52 (18)C12—C13—H13126.2
C6—Fe1—C868.82 (13)Fe1—C13—H13126.5
C11—Fe1—C8159.14 (19)C15—C14—C13109.2 (5)
C9—Fe1—C840.52 (14)C15—C14—Fe169.5 (3)
C7—Fe1—C840.53 (14)C13—C14—Fe170.7 (3)
C12—Fe1—C8123.74 (18)C15—C14—H14125.4
C13—Fe1—C8109.26 (17)C13—C14—H14125.4
C5—N1—C1118.1 (3)Fe1—C14—H14126.0
C1—N2—H2A120.0C14—C15—C11108.1 (5)
C1—N2—H2B120.0C14—C15—Fe170.5 (3)
H2A—N2—H2B120.0C11—C15—Fe170.2 (3)
N2—C1—N1116.0 (3)C14—C15—H15126.0
N2—C1—C2122.2 (3)C11—C15—H15126.0
N1—C1—C2121.8 (3)Fe1—C15—H15125.0
C3—C2—C1119.8 (3)N3—C16—C2175.2 (4)
C3—C2—C16122.6 (3)C18—C17—C22117.9 (3)
C1—C2—C16117.6 (3)C18—C17—C3121.7 (3)
C4—C3—C2117.2 (3)C22—C17—C3120.4 (3)
C4—C3—C17120.7 (3)C17—C18—C19121.7 (4)
C2—C3—C17122.0 (3)C17—C18—H18119.2
C3—C4—C5119.9 (3)C19—C18—H18119.2
C3—C4—H4120.0C20—C19—C18119.2 (4)
C5—C4—H4120.0C20—C19—H19120.4
N1—C5—C4123.1 (3)C18—C19—H19120.4
N1—C5—C6115.2 (3)C19—C20—C21120.7 (4)
C4—C5—C6121.7 (3)C19—C20—Cl1120.0 (3)
C10—C6—C7107.0 (3)C21—C20—Cl1119.3 (3)
C10—C6—C5125.2 (3)C20—C21—C22119.5 (4)
C7—C6—C5127.8 (3)C20—C21—H21120.3
C10—C6—Fe168.9 (2)C22—C21—H21120.3
C7—C6—Fe169.73 (19)C21—C22—C17121.0 (4)
C5—C6—Fe1124.7 (2)C21—C22—H22119.5
C8—C7—C6108.4 (3)C17—C22—H22119.5
C8—C7—Fe170.2 (2)
C5—N1—C1—N2−178.8 (3)C13—Fe1—C10—C9−52.3 (5)
C5—N1—C1—C22.2 (5)C8—Fe1—C10—C937.1 (2)
N2—C1—C2—C3−179.8 (3)C15—Fe1—C10—C6119.0 (2)
N1—C1—C2—C3−0.9 (5)C14—Fe1—C10—C6159.6 (2)
N2—C1—C2—C160.9 (5)C11—Fe1—C10—C678.3 (3)
N1—C1—C2—C16179.8 (3)C9—Fe1—C10—C6−119.1 (3)
C1—C2—C3—C4−1.4 (5)C7—Fe1—C10—C6−38.3 (2)
C16—C2—C3—C4177.8 (3)C12—Fe1—C10—C651.3 (6)
C1—C2—C3—C17175.5 (3)C13—Fe1—C10—C6−171.4 (4)
C16—C2—C3—C17−5.3 (5)C8—Fe1—C10—C6−81.9 (2)
C2—C3—C4—C52.3 (5)C10—Fe1—C11—C1574.5 (3)
C17—C3—C4—C5−174.6 (3)C14—Fe1—C11—C15−37.6 (3)
C1—N1—C5—C4−1.3 (5)C6—Fe1—C11—C15117.0 (3)
C1—N1—C5—C6−179.9 (3)C9—Fe1—C11—C1541.7 (6)
C3—C4—C5—N1−1.1 (5)C7—Fe1—C11—C15159.3 (3)
C3—C4—C5—C6177.5 (3)C12—Fe1—C11—C15−118.8 (4)
N1—C5—C6—C1010.9 (5)C13—Fe1—C11—C15−81.0 (3)
C4—C5—C6—C10−167.8 (3)C8—Fe1—C11—C15−167.5 (4)
N1—C5—C6—C7−166.7 (3)C15—Fe1—C11—C12118.8 (4)
C4—C5—C6—C714.6 (6)C10—Fe1—C11—C12−166.7 (3)
N1—C5—C6—Fe1−76.5 (4)C14—Fe1—C11—C1281.2 (3)
C4—C5—C6—Fe1104.9 (4)C6—Fe1—C11—C12−124.2 (3)
C15—Fe1—C6—C10−78.2 (3)C9—Fe1—C11—C12160.5 (4)
C14—Fe1—C6—C10−46.9 (5)C7—Fe1—C11—C12−81.9 (3)
C11—Fe1—C6—C10−120.5 (2)C13—Fe1—C11—C1237.8 (3)
C9—Fe1—C6—C1037.6 (2)C8—Fe1—C11—C12−48.6 (6)
C7—Fe1—C6—C10118.5 (3)C15—C11—C12—C13−0.8 (5)
C12—Fe1—C6—C10−161.7 (2)Fe1—C11—C12—C13−59.9 (3)
C13—Fe1—C6—C10168.2 (5)C15—C11—C12—Fe159.1 (3)
C8—Fe1—C6—C1081.2 (2)C15—Fe1—C12—C1380.8 (3)
C15—Fe1—C6—C7163.4 (2)C10—Fe1—C12—C13154.6 (5)
C10—Fe1—C6—C7−118.5 (3)C14—Fe1—C12—C1337.4 (3)
C14—Fe1—C6—C7−165.4 (4)C6—Fe1—C12—C13−166.5 (3)
C11—Fe1—C6—C7121.0 (3)C11—Fe1—C12—C13118.7 (4)
C9—Fe1—C6—C7−80.9 (2)C9—Fe1—C12—C13−42.5 (6)
C12—Fe1—C6—C779.9 (3)C7—Fe1—C12—C13−123.0 (3)
C13—Fe1—C6—C749.8 (6)C8—Fe1—C12—C13−80.0 (3)
C8—Fe1—C6—C7−37.3 (2)C15—Fe1—C12—C11−37.9 (3)
C15—Fe1—C6—C540.8 (4)C10—Fe1—C12—C1135.9 (7)
C10—Fe1—C6—C5118.9 (4)C14—Fe1—C12—C11−81.3 (3)
C14—Fe1—C6—C572.1 (5)C6—Fe1—C12—C1174.8 (3)
C11—Fe1—C6—C5−1.6 (4)C9—Fe1—C12—C11−161.2 (4)
C9—Fe1—C6—C5156.5 (3)C7—Fe1—C12—C11118.3 (3)
C7—Fe1—C6—C5−122.6 (4)C13—Fe1—C12—C11−118.7 (4)
C12—Fe1—C6—C5−42.7 (4)C8—Fe1—C12—C11161.3 (3)
C13—Fe1—C6—C5−72.8 (6)C11—C12—C13—C140.4 (5)
C8—Fe1—C6—C5−159.8 (3)Fe1—C12—C13—C14−59.1 (3)
C10—C6—C7—C80.4 (4)C11—C12—C13—Fe159.5 (3)
C5—C6—C7—C8178.3 (3)C15—Fe1—C13—C1436.9 (3)
Fe1—C6—C7—C859.5 (3)C10—Fe1—C13—C14−40.8 (6)
C10—C6—C7—Fe1−59.1 (2)C6—Fe1—C13—C14158.3 (5)
C5—C6—C7—Fe1118.8 (4)C11—Fe1—C13—C1481.0 (3)
C15—Fe1—C7—C8−160.1 (4)C9—Fe1—C13—C14−78.2 (3)
C10—Fe1—C7—C8−81.3 (2)C7—Fe1—C13—C14−163.3 (3)
C14—Fe1—C7—C841.0 (6)C12—Fe1—C13—C14119.0 (4)
C6—Fe1—C7—C8−119.7 (3)C8—Fe1—C13—C14−121.2 (3)
C11—Fe1—C7—C8162.5 (2)C15—Fe1—C13—C12−82.1 (3)
C9—Fe1—C7—C8−37.6 (2)C10—Fe1—C13—C12−159.8 (4)
C12—Fe1—C7—C8119.2 (2)C14—Fe1—C13—C12−119.0 (4)
C13—Fe1—C7—C876.9 (3)C6—Fe1—C13—C1239.3 (7)
C15—Fe1—C7—C6−40.4 (5)C11—Fe1—C13—C12−38.1 (3)
C10—Fe1—C7—C638.39 (19)C9—Fe1—C13—C12162.8 (3)
C14—Fe1—C7—C6160.7 (5)C7—Fe1—C13—C1277.7 (3)
C11—Fe1—C7—C6−77.8 (3)C8—Fe1—C13—C12119.8 (3)
C9—Fe1—C7—C682.1 (2)C12—C13—C14—C150.2 (5)
C12—Fe1—C7—C6−121.1 (2)Fe1—C13—C14—C15−59.0 (3)
C13—Fe1—C7—C6−163.4 (2)C12—C13—C14—Fe159.2 (3)
C8—Fe1—C7—C6119.7 (3)C10—Fe1—C14—C15−77.8 (3)
C6—C7—C8—C9−0.2 (4)C6—Fe1—C14—C15−44.1 (5)
Fe1—C7—C8—C958.6 (3)C11—Fe1—C14—C1538.3 (3)
C6—C7—C8—Fe1−58.8 (2)C9—Fe1—C14—C15−120.1 (3)
C15—Fe1—C8—C939.2 (6)C7—Fe1—C14—C15167.7 (5)
C10—Fe1—C8—C9−37.2 (2)C12—Fe1—C14—C1582.4 (3)
C14—Fe1—C8—C975.2 (3)C13—Fe1—C14—C15120.2 (4)
C6—Fe1—C8—C9−81.6 (2)C8—Fe1—C14—C15−161.1 (3)
C11—Fe1—C8—C9−164.4 (4)C15—Fe1—C14—C13−120.2 (4)
C7—Fe1—C8—C9−119.3 (3)C10—Fe1—C14—C13162.0 (3)
C12—Fe1—C8—C9159.6 (2)C6—Fe1—C14—C13−164.3 (3)
C13—Fe1—C8—C9117.1 (2)C11—Fe1—C14—C13−82.0 (3)
C15—Fe1—C8—C7158.6 (5)C9—Fe1—C14—C13119.7 (3)
C10—Fe1—C8—C782.2 (2)C7—Fe1—C14—C1347.5 (7)
C14—Fe1—C8—C7−165.5 (3)C12—Fe1—C14—C13−37.8 (3)
C6—Fe1—C8—C737.8 (2)C8—Fe1—C14—C1378.6 (3)
C11—Fe1—C8—C7−45.0 (6)C13—C14—C15—C11−0.7 (5)
C9—Fe1—C8—C7119.3 (3)Fe1—C14—C15—C11−60.4 (3)
C12—Fe1—C8—C7−81.0 (3)C13—C14—C15—Fe159.7 (3)
C13—Fe1—C8—C7−123.6 (2)C12—C11—C15—C140.9 (5)
C7—C8—C9—C10−0.1 (4)Fe1—C11—C15—C1460.6 (3)
Fe1—C8—C9—C1058.7 (3)C12—C11—C15—Fe1−59.6 (3)
C7—C8—C9—Fe1−58.8 (3)C10—Fe1—C15—C14118.6 (3)
C15—Fe1—C9—C1075.2 (3)C6—Fe1—C15—C14160.5 (3)
C14—Fe1—C9—C10116.3 (3)C11—Fe1—C15—C14−118.5 (4)
C6—Fe1—C9—C10−38.2 (2)C9—Fe1—C15—C1477.9 (3)
C11—Fe1—C9—C1044.4 (6)C7—Fe1—C15—C14−169.8 (4)
C7—Fe1—C9—C10−82.5 (2)C12—Fe1—C15—C14−80.6 (3)
C12—Fe1—C9—C10−171.5 (4)C13—Fe1—C15—C14−36.9 (3)
C13—Fe1—C9—C10157.5 (2)C8—Fe1—C15—C1448.8 (6)
C8—Fe1—C9—C10−120.1 (3)C10—Fe1—C15—C11−122.9 (3)
C15—Fe1—C9—C8−164.7 (2)C14—Fe1—C15—C11118.5 (4)
C10—Fe1—C9—C8120.1 (3)C6—Fe1—C15—C11−80.9 (3)
C14—Fe1—C9—C8−123.5 (2)C9—Fe1—C15—C11−163.6 (3)
C6—Fe1—C9—C881.9 (2)C7—Fe1—C15—C11−51.3 (6)
C11—Fe1—C9—C8164.5 (4)C12—Fe1—C15—C1137.9 (3)
C7—Fe1—C9—C837.6 (2)C13—Fe1—C15—C1181.7 (3)
C12—Fe1—C9—C8−51.3 (5)C8—Fe1—C15—C11167.4 (4)
C13—Fe1—C9—C8−82.4 (3)C4—C3—C17—C18126.9 (4)
C8—C9—C10—C60.4 (4)C2—C3—C17—C18−49.8 (5)
Fe1—C9—C10—C659.8 (2)C4—C3—C17—C22−51.3 (5)
C8—C9—C10—Fe1−59.4 (3)C2—C3—C17—C22131.9 (4)
C7—C6—C10—C9−0.5 (4)C22—C17—C18—C191.1 (6)
C5—C6—C10—C9−178.5 (3)C3—C17—C18—C19−177.2 (4)
Fe1—C6—C10—C9−60.1 (2)C17—C18—C19—C20−0.2 (6)
C7—C6—C10—Fe159.6 (2)C18—C19—C20—C21−1.1 (6)
C5—C6—C10—Fe1−118.4 (3)C18—C19—C20—Cl1178.5 (3)
C15—Fe1—C10—C9−122.0 (3)C19—C20—C21—C221.5 (6)
C14—Fe1—C10—C9−81.3 (3)Cl1—C20—C21—C22−178.0 (3)
C6—Fe1—C10—C9119.1 (3)C20—C21—C22—C17−0.7 (6)
C11—Fe1—C10—C9−162.6 (3)C18—C17—C22—C21−0.6 (6)
C7—Fe1—C10—C980.8 (2)C3—C17—C22—C21177.7 (3)
C12—Fe1—C10—C9170.4 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N3i0.862.283.047 (5)149
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N3i0.862.283.047 (5)149
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (grant No. 20672090) and the Natural Science Foundation of Jiangsu Province (grant No. BK2006033) for financial support.

references
References top

Alyoubi, A. O. (2000). Spectrochim. Acta Part A, 56, 2397–2404.

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Desai, J. M. & Shah, V. H. (2003). Indian J. Chem. Sect. B, 42, 382–385.

Dombrowski, K. E., Baldwin, W. & Sheats, J. E. (1986). J. Organomet. Chem. 302, 281–306.

Murata, T., Shimada, M., Sakakibara, S., Yoshino, T., Masuda, T., Shintani, T., Sato, H., Koriyama, Y., Fukushima, K., Nunami, N., Yamauchi, M., Fuchikami, K., Komura, H., Watanabe, A., Ziegelbauer, K. B., Bacon, K. B. & Lowinger, T. B. (2004). Bioorg. Med. Chem. Lett. 14, 4019–4022.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.