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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m730.
Published online 2008 April 26. doi:  10.1107/S1600536808008714
PMCID: PMC2961127

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

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0m730-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C17H11ClN3)]
  • M r = 413.68
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m730-efi1.jpg
  • a = 12.1517 (13) Å
  • b = 7.4214 (11) Å
  • c = 20.742 (2) Å
  • β = 97.691 (2)°
  • V = 1853.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.97 mm−1
  • T = 298 (2) K
  • 0.20 × 0.15 × 0.09 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.830, T max = 0.918
  • 8876 measured reflections
  • 3260 independent reflections
  • 2298 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.093
  • S = 1.09
  • 3260 reflections
  • 244 parameters
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008714/hk2443sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008714/hk2443Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
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.

Crystal data

[Fe(C5H5)(C17H11ClN3)]F000 = 848
Mr = 413.68Dx = 1.482 Mg m3
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 mm1
β = 97.691 (2)ºT = 298 (2) K
V = 1853.7 (4) Å3Block, red
Z = 40.20 × 0.15 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer3260 independent reflections
Radiation source: fine-focus sealed tube2298 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 298(2) Kθmax = 25.0º
[var phi] 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

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 Å3
244 parametersΔρmin = −0.43 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2443).

References

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