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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1543.
Published online 2010 November 10. doi:  10.1107/S1600536810045459
PMCID: PMC3011590

19-Ferrocenyl-18-oxa-8,16-diaza­penta­cyclo­[8.6.3.01,10.02,7.012,16]nona­deca-2(7),3,5-triene-9,17-dione

Abstract

In the title compound, [Fe(C5H5)(C21H19N2O3)], both pyrrol­idine rings of the pyrrolizine substructure show an envelope conformation. In the ferrocenyl moiety, the unsubstituted cyclo­penta­dienyl ring is disordered over two orientations with site occupancies of 0.64 (2) and 0.36 (2). In the pyrrolizine ring, one C atom is disordered over two positions, with site occupancies of 0.71 (1) and 0.29 (1). Intra­molecular C—H(...)O inter­actions occur. The crystal packing is established through weak inter­molecular C—H(...)O and N—H(...)O inter­actions.

Related literature

For the biological activity of ferrocene derivatives, see: Fouda et al. (2007 [triangle]); Jaouen et al. (2004 [triangle]); Biot et al. (2004 [triangle]). For related structures, see: Kamala et al. (2009 [triangle]); Gunasekaran et al. (2009 [triangle]);

An external file that holds a picture, illustration, etc.
Object name is e-66-m1543-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C21H19N2O3)]
  • M r = 468.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1543-efi1.jpg
  • a = 9.6486 (7) Å
  • b = 18.8900 (13) Å
  • c = 11.8207 (9) Å
  • β = 93.248 (5)°
  • V = 2151.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.73 mm−1
  • T = 295 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.864, T max = 0.867
  • 20500 measured reflections
  • 5308 independent reflections
  • 3322 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.123
  • S = 1.01
  • 5308 reflections
  • 344 parameters
  • 5 restraints
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045459/im2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045459/im2240Isup2.hkl

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

Acknowledgments

BG thanks AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

Metallocenes exhibit antibacterial (Fouda et al., 2007), antitumor (Jaouen et al., 2004), antimalarial and antifungal (Biot et al., 2004) activities. The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Kamala et al., 2009; Gunasekaran et al., 2009). N9c atom adopts sp3 hybridization [sum of bond angles around N9c is 332.69 (2) °].

In the ferrocenyl moiety, one cyclopentadienyl (Cp) ring is disordered over two orientations [site occupancies of 0.64 (2) and 0.36 (2), respectively]. In the pyrrolizine ring one C atom is disordered over two positions [site occupancies of C12 and C12A are 0.71 (1) and 0.29 (1), respectively]. Crystal packing is established through weak intermolecular C—H···O and N—H···O interactions.

Experimental

A mixture of methyl-2-hydroxy ferrocenyl methyl acrylate (1 mmol), isatin (1 mmol) and proline (1 mmol) was refluxed in methanol for 12 h until completion of the reaction was evidenced by TLC analysis. After completion of the reaction the solvent was evaporated under reduced pressure. The crude mixture was purified by column chromatography using ethyl acetate and hexane as eluent (10: 90). The product was dissolved in a methanol/chloroform mixture and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvents for 48 hours resulting in the formation of single crystals (yield 65%).

Refinement

Site occupancy factors of disordered C atoms in the Cp ring were refined as 0.64 (C19-C23) and 0.36 (C19A-C23A). Disorder in the pyrrolizine system was refined to sof's of C12 = 0.71 (1) and C12A = 0.29 (1). Carbon-carbon bond distances in the disordered Cp ligand (C19A-C23A) were restrained to 1.450 (1) Å. H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C) for aromatic C—H groups, C—H = 0.98 Å and Uiso(H) = 1.2 Ueq(C) for methine groups, C—H = 0.97 Å and Uiso(H) = 1.2 Ueq(C) for CH2 and N—H = 0.86 Å and Uiso(H) = 1.2 Ueq(C) for the NH function of the quinoline moiety.

Figures

Fig. 1.
Molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Crystal structure of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

[Fe(C5H5)(C21H19N2O3)]F(000) = 976
Mr = 468.32Dx = 1.446 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4218 reflections
a = 9.6486 (7) Åθ = 2.4–22.9°
b = 18.8900 (13) ŵ = 0.73 mm1
c = 11.8207 (9) ÅT = 295 K
β = 93.248 (5)°Block, colourless
V = 2151.0 (3) Å30.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer5308 independent reflections
Radiation source: fine-focus sealed tube3322 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 0 pixels mm-1θmax = 28.3°, θmin = 2.0°
ω and [var phi] scansh = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −25→24
Tmin = 0.864, Tmax = 0.867l = −15→15
20500 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0546P)2 + 0.6413P] where P = (Fo2 + 2Fc2)/3
5308 reflections(Δ/σ)max < 0.001
344 parametersΔρmax = 0.46 e Å3
5 restraintsΔρmin = −0.24 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
C140.4486 (2)0.25037 (13)0.0771 (2)0.0425 (6)
C150.4509 (3)0.29893 (15)0.1679 (2)0.0548 (7)
H150.52810.32320.19840.066*
C160.3125 (3)0.30383 (17)0.2043 (3)0.0636 (8)
H160.28410.33220.26300.076*
C170.2269 (3)0.25912 (16)0.1374 (3)0.0633 (8)
H170.13220.25240.14370.076*
C180.3100 (3)0.22591 (14)0.0585 (3)0.0517 (7)
H180.27910.19350.00350.062*
C30.5667 (2)0.22556 (12)0.0118 (2)0.0395 (5)
H30.53010.2093−0.06270.047*
C3A0.6577 (2)0.16611 (12)0.0667 (2)0.0364 (5)
C9B0.7977 (2)0.17698 (12)0.0127 (2)0.0365 (5)
C10.7951 (3)0.25757 (12)−0.0064 (2)0.0396 (5)
C100.6978 (3)0.17695 (13)0.1924 (2)0.0437 (6)
H10A0.69520.22680.21220.052*
H10B0.63550.15120.23920.052*
C10A0.8450 (3)0.14799 (14)0.2076 (2)0.0489 (6)
H10C0.89680.17520.26650.059*
C110.8590 (4)0.06879 (16)0.2343 (3)0.0718 (9)
H11A0.76890.04790.24510.086*
H11B0.91830.06130.30220.086*
C120.9244 (7)0.0365 (3)0.1300 (5)0.075 (2)0.708 (12)
H12A0.9907−0.00020.15240.089*0.708 (12)
H12B0.85380.01660.07770.089*0.708 (12)
C12A0.9983 (15)0.0539 (7)0.1800 (12)0.065 (4)*0.292 (12)
H12C1.07610.06790.23070.078*0.292 (12)
H12D1.00710.00410.16210.078*0.292 (12)
C130.9927 (3)0.09571 (18)0.0797 (3)0.0738 (10)
H13A1.00050.0876−0.00070.089*
H13B1.08520.10180.11490.089*
C9A0.8044 (2)0.14275 (12)−0.1028 (2)0.0382 (5)
C90.9033 (3)0.16238 (13)−0.1781 (2)0.0455 (6)
H90.96710.1976−0.15760.055*
C80.9081 (3)0.13042 (15)−0.2823 (2)0.0558 (7)
H80.97460.1440−0.33190.067*
C70.8138 (3)0.07823 (15)−0.3128 (2)0.0599 (8)
H70.81590.0572−0.38380.072*
C60.7164 (3)0.05681 (14)−0.2394 (2)0.0545 (7)
H60.65370.0211−0.26030.065*
C5A0.7126 (3)0.08898 (12)−0.1334 (2)0.0412 (6)
C40.5898 (2)0.09531 (13)0.0413 (2)0.0414 (6)
N9C0.9090 (2)0.15864 (11)0.09766 (18)0.0469 (5)
N50.6147 (2)0.06523 (11)−0.05809 (18)0.0474 (5)
H5A0.56700.0283−0.07750.057*
O20.66395 (17)0.28264 (8)−0.00449 (15)0.0450 (4)
O10.89048 (18)0.29575 (9)−0.02222 (15)0.0506 (5)
O30.5114 (2)0.06791 (9)0.10763 (16)0.0592 (5)
Fe10.31975 (4)0.332977 (19)0.03953 (3)0.04542 (14)
C190.4021 (12)0.4127 (9)−0.0405 (13)0.074 (5)0.64 (2)
H190.49500.4248−0.02740.089*0.64 (2)
C200.2958 (16)0.4379 (6)0.0168 (10)0.071 (3)0.64 (2)
H200.30170.47250.07280.086*0.64 (2)
C210.1752 (11)0.4029 (7)−0.0230 (10)0.059 (3)0.64 (2)
H210.08710.40770.00420.071*0.64 (2)
C220.2133 (15)0.3587 (7)−0.1127 (11)0.062 (3)0.64 (2)
H220.15610.3294−0.15830.074*0.64 (2)
C230.3532 (15)0.3686 (8)−0.1174 (12)0.069 (5)0.64 (2)
H230.40720.3464−0.16950.083*0.64 (2)
C21A0.208 (2)0.4262 (11)0.025 (3)0.082 (7)0.36 (2)
H21A0.13980.44460.06920.099*0.36 (2)
C22A0.1881 (14)0.3788 (11)−0.071 (2)0.057 (6)0.36 (2)
H22A0.10270.3598−0.09590.068*0.36 (2)
C20A0.356 (3)0.4385 (14)0.037 (2)0.085 (7)0.36 (2)
H20A0.40400.46080.09700.103*0.36 (2)
C19A0.416 (2)0.4096 (16)−0.063 (3)0.082 (10)0.36 (2)
H19A0.50550.4189−0.08490.099*0.36 (2)
C23A0.317 (3)0.3643 (17)−0.125 (2)0.082 (10)0.36 (2)
H23A0.33180.3334−0.18410.098*0.36 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C140.0374 (13)0.0417 (14)0.0488 (15)−0.0002 (10)0.0060 (11)0.0036 (11)
C150.0537 (16)0.0603 (18)0.0507 (17)0.0089 (14)0.0039 (13)−0.0031 (14)
C160.068 (2)0.071 (2)0.0535 (18)0.0225 (17)0.0214 (15)0.0048 (15)
C170.0494 (16)0.0603 (18)0.083 (2)0.0066 (14)0.0256 (16)0.0236 (16)
C180.0410 (14)0.0417 (14)0.073 (2)−0.0031 (11)0.0070 (13)0.0075 (13)
C30.0372 (12)0.0375 (13)0.0445 (14)−0.0048 (10)0.0072 (10)−0.0004 (10)
C3A0.0370 (12)0.0345 (12)0.0381 (13)−0.0042 (10)0.0074 (10)−0.0013 (10)
C9B0.0350 (12)0.0332 (12)0.0419 (14)−0.0050 (9)0.0086 (10)0.0004 (10)
C10.0423 (13)0.0396 (13)0.0379 (13)−0.0048 (10)0.0100 (10)−0.0018 (10)
C100.0490 (14)0.0437 (14)0.0390 (14)−0.0039 (11)0.0076 (11)−0.0009 (11)
C10A0.0528 (15)0.0535 (16)0.0401 (15)0.0008 (12)0.0002 (12)−0.0028 (12)
C110.074 (2)0.070 (2)0.071 (2)0.0129 (17)0.0075 (17)0.0261 (17)
C120.075 (4)0.053 (3)0.095 (4)0.015 (2)−0.005 (3)−0.005 (3)
C130.071 (2)0.082 (2)0.071 (2)0.0344 (18)0.0142 (17)0.0149 (18)
C9A0.0403 (12)0.0330 (12)0.0421 (14)−0.0007 (10)0.0087 (10)0.0004 (10)
C90.0498 (14)0.0385 (13)0.0499 (15)−0.0008 (11)0.0171 (12)0.0034 (11)
C80.0698 (19)0.0482 (16)0.0519 (17)0.0052 (14)0.0269 (14)0.0054 (13)
C70.080 (2)0.0594 (18)0.0417 (16)0.0027 (16)0.0164 (14)−0.0074 (13)
C60.0620 (17)0.0470 (15)0.0551 (17)−0.0063 (13)0.0084 (14)−0.0101 (13)
C5A0.0460 (13)0.0367 (13)0.0414 (14)−0.0017 (11)0.0081 (11)−0.0006 (10)
C40.0411 (13)0.0366 (12)0.0471 (15)−0.0057 (10)0.0082 (11)−0.0017 (11)
N9C0.0391 (11)0.0504 (13)0.0514 (13)0.0026 (9)0.0038 (10)0.0067 (10)
N50.0500 (12)0.0400 (12)0.0532 (13)−0.0152 (10)0.0131 (10)−0.0084 (10)
O20.0419 (9)0.0347 (9)0.0595 (11)−0.0027 (7)0.0114 (8)0.0052 (8)
O10.0513 (11)0.0442 (10)0.0579 (12)−0.0156 (8)0.0165 (9)−0.0021 (8)
O30.0684 (12)0.0494 (11)0.0628 (13)−0.0222 (9)0.0303 (10)−0.0050 (9)
Fe10.0401 (2)0.0419 (2)0.0552 (3)0.00089 (16)0.01126 (16)0.00516 (17)
C190.059 (6)0.080 (9)0.082 (8)−0.029 (6)−0.004 (7)0.033 (6)
C200.110 (10)0.038 (4)0.066 (6)0.015 (6)0.002 (6)−0.003 (3)
C210.064 (4)0.056 (8)0.060 (8)0.027 (5)0.027 (5)0.015 (5)
C220.066 (6)0.064 (6)0.055 (6)0.010 (4)0.003 (4)0.005 (4)
C230.072 (5)0.064 (9)0.075 (9)0.010 (6)0.033 (6)0.029 (7)
C21A0.103 (16)0.052 (10)0.098 (16)0.029 (10)0.059 (13)0.014 (9)
C22A0.035 (8)0.057 (16)0.08 (2)−0.002 (9)−0.002 (10)0.019 (11)
C20A0.119 (17)0.059 (8)0.074 (12)−0.028 (11)−0.022 (12)0.014 (8)
C19A0.068 (10)0.055 (12)0.13 (2)0.003 (8)0.063 (13)0.043 (13)
C23A0.105 (19)0.072 (12)0.064 (13)−0.027 (14)−0.030 (14)−0.002 (9)

Geometric parameters (Å, °)

C14—C151.411 (4)C13—H13A0.9700
C14—C181.421 (3)C13—H13B0.9700
C14—C31.488 (3)C9A—C5A1.382 (3)
C14—Fe12.029 (2)C9A—C91.391 (3)
C15—C161.429 (4)C9—C81.375 (4)
C15—Fe12.025 (3)C9—H90.9300
C15—H150.9300C8—C71.376 (4)
C16—C171.395 (4)C8—H80.9300
C16—Fe12.029 (3)C7—C61.375 (4)
C16—H160.9300C7—H70.9300
C17—C181.411 (4)C6—C5A1.395 (3)
C17—Fe12.050 (3)C6—H60.9300
C17—H170.9300C5A—N51.407 (3)
C18—Fe12.038 (3)C4—O31.233 (3)
C18—H180.9300C4—N51.339 (3)
C3—O21.449 (3)N5—H5A0.8600
C3—C3A1.546 (3)Fe1—C191.970 (16)
C3—H30.9800Fe1—C22A1.973 (15)
C3A—C41.512 (3)Fe1—C202.012 (11)
C3A—C101.528 (3)Fe1—C232.016 (15)
C3A—C9B1.540 (3)Fe1—C20A2.02 (3)
C9B—N9C1.469 (3)Fe1—C23A2.03 (3)
C9B—C9A1.516 (3)Fe1—C212.030 (10)
C9B—C11.539 (3)C19—C231.301 (14)
C1—O11.193 (3)C19—C201.348 (14)
C1—O21.352 (3)C19—H190.9300
C10—C10A1.523 (4)C20—C211.397 (15)
C10—H10A0.9700C20—H200.9300
C10—H10B0.9700C21—C221.415 (11)
C10A—N9C1.484 (3)C21—H210.9300
C10A—C111.533 (4)C22—C231.367 (15)
C10A—H10C0.9800C22—H220.9300
C11—C121.542 (6)C23—H230.9300
C11—C12A1.547 (12)C21A—C22A1.4499 (10)
C11—H11A0.9700C21A—C20A1.4499 (10)
C11—H11B0.9700C21A—H21A0.9300
C12—C131.443 (6)C22A—C23A1.4499 (10)
C12—H12A0.9700C22A—H22A0.9300
C12—H12B0.9700C20A—C19A1.4499 (10)
C12A—C131.423 (12)C20A—H20A0.9300
C12A—H12C0.9700C19A—C23A1.4500 (10)
C12A—H12D0.9700C19A—H19A0.9300
C13—N9C1.459 (4)C23A—H23A0.9300
C15—C14—C18107.7 (2)C19—Fe1—C2338.1 (4)
C15—C14—C3128.3 (2)C22A—Fe1—C2351.2 (7)
C18—C14—C3124.0 (2)C20—Fe1—C2364.6 (5)
C15—C14—Fe169.49 (15)C19—Fe1—C20A33.3 (9)
C18—C14—Fe169.88 (14)C22A—Fe1—C20A70.3 (6)
C3—C14—Fe1127.32 (17)C20—Fe1—C20A17.5 (5)
C14—C15—C16107.2 (3)C23—Fe1—C20A67.5 (8)
C14—C15—Fe169.78 (15)C19—Fe1—C15110.5 (4)
C16—C15—Fe169.52 (17)C22A—Fe1—C15171.4 (9)
C14—C15—H15126.4C20—Fe1—C15118.4 (4)
C16—C15—H15126.4C23—Fe1—C15132.0 (4)
Fe1—C15—H15125.9C20A—Fe1—C15103.0 (6)
C17—C16—C15108.9 (3)C19—Fe1—C14115.8 (5)
C17—C16—Fe170.83 (17)C22A—Fe1—C14147.8 (9)
C15—C16—Fe169.22 (16)C20—Fe1—C14148.4 (4)
C17—C16—H16125.6C23—Fe1—C14109.3 (4)
C15—C16—H16125.6C20A—Fe1—C14131.0 (7)
Fe1—C16—H16126.0C15—Fe1—C1440.74 (10)
C16—C17—C18107.7 (3)C19—Fe1—C23A45.7 (9)
C16—C17—Fe169.18 (17)C22A—Fe1—C23A42.5 (4)
C18—C17—Fe169.32 (15)C20—Fe1—C23A65.8 (9)
C16—C17—H17126.2C23—Fe1—C23A10.4 (8)
C18—C17—H17126.2C20A—Fe1—C23A71.9 (9)
Fe1—C17—H17126.9C15—Fe1—C23A141.7 (7)
C17—C18—C14108.5 (3)C14—Fe1—C23A114.2 (8)
C17—C18—Fe170.30 (16)C19—Fe1—C16134.9 (4)
C14—C18—Fe169.22 (14)C22A—Fe1—C16134.5 (7)
C17—C18—H18125.7C20—Fe1—C16112.7 (3)
C14—C18—H18125.7C23—Fe1—C16171.7 (5)
Fe1—C18—H18126.3C20A—Fe1—C16107.4 (7)
O2—C3—C14110.80 (19)C15—Fe1—C1641.27 (11)
O2—C3—C3A103.87 (18)C14—Fe1—C1668.58 (11)
C14—C3—C3A116.4 (2)C23A—Fe1—C16177.0 (7)
O2—C3—H3108.5C19—Fe1—C2167.4 (5)
C14—C3—H3108.5C22A—Fe1—C2121.4 (6)
C3A—C3—H3108.5C20—Fe1—C2140.4 (4)
C4—C3A—C10113.23 (19)C23—Fe1—C2165.8 (5)
C4—C3A—C9B114.61 (19)C20A—Fe1—C2157.9 (6)
C10—C3A—C9B101.88 (19)C15—Fe1—C21150.1 (4)
C4—C3A—C3109.24 (19)C14—Fe1—C21168.6 (4)
C10—C3A—C3114.67 (19)C23A—Fe1—C2159.3 (7)
C9B—C3A—C3102.71 (18)C16—Fe1—C21117.8 (3)
N9C—C9B—C9A116.66 (19)C19—Fe1—C18146.5 (5)
N9C—C9B—C1109.81 (19)C22A—Fe1—C18118.4 (6)
C9A—C9B—C1106.91 (18)C20—Fe1—C18170.7 (4)
N9C—C9B—C3A108.05 (18)C23—Fe1—C18116.3 (4)
C9A—C9B—C3A113.53 (19)C20A—Fe1—C18171.2 (7)
C1—C9B—C3A100.65 (18)C15—Fe1—C1868.49 (11)
O1—C1—O2121.5 (2)C14—Fe1—C1840.90 (10)
O1—C1—C9B127.9 (2)C23A—Fe1—C18113.3 (8)
O2—C1—C9B110.60 (18)C16—Fe1—C1867.72 (13)
C10A—C10—C3A104.41 (19)C21—Fe1—C18130.6 (4)
C10A—C10—H10A110.9C19—Fe1—C17172.9 (5)
C3A—C10—H10A110.9C22A—Fe1—C17112.8 (4)
C10A—C10—H10B110.9C20—Fe1—C17134.1 (4)
C3A—C10—H10B110.9C23—Fe1—C17147.6 (5)
H10A—C10—H10B108.9C20A—Fe1—C17139.6 (8)
N9C—C10A—C10106.3 (2)C15—Fe1—C1768.62 (12)
N9C—C10A—C11106.0 (2)C14—Fe1—C1768.59 (10)
C10—C10A—C11116.5 (2)C23A—Fe1—C17139.1 (8)
N9C—C10A—H10C109.3C16—Fe1—C1739.99 (13)
C10—C10A—H10C109.3C21—Fe1—C17109.6 (3)
C11—C10A—H10C109.3C18—Fe1—C1740.38 (11)
C10A—C11—C12104.9 (3)C23—C19—C20108.7 (9)
C10A—C11—C12A99.2 (5)C23—C19—Fe172.9 (9)
C10A—C11—H11A110.8C20—C19—Fe171.9 (8)
C12—C11—H11A110.8C23—C19—H19125.7
C12A—C11—H11A141.9C20—C19—H19125.7
C10A—C11—H11B110.8Fe1—C19—H19121.3
C12—C11—H11B110.8C19—C20—C21107.9 (7)
C12A—C11—H11B80.3C19—C20—Fe168.5 (8)
H11A—C11—H11B108.8C21—C20—Fe170.4 (6)
C13—C12—C11103.9 (4)C19—C20—H20126.1
C13—C12—H12A111.0C21—C20—H20126.1
C11—C12—H12A111.0Fe1—C20—H20126.5
C13—C12—H12B111.0C20—C21—C22106.6 (10)
C11—C12—H12B111.0C20—C21—Fe169.1 (6)
H12A—C12—H12B109.0C22—C21—Fe171.7 (8)
C13—C12A—C11104.6 (8)C20—C21—H21126.7
C13—C12A—H12C110.8C22—C21—H21126.7
C11—C12A—H12C110.8Fe1—C21—H21124.1
C13—C12A—H12D110.8C23—C22—C21104.3 (14)
C11—C12A—H12D110.8C23—C22—Fe168.0 (9)
H12C—C12A—H12D108.9C21—C22—Fe168.0 (8)
C12A—C13—N9C109.0 (5)C23—C22—H22127.8
C12—C13—N9C107.6 (3)C21—C22—H22127.8
C12A—C13—H13A136.7Fe1—C22—H22127.6
C12—C13—H13A110.2C19—C23—C22112.4 (12)
N9C—C13—H13A110.2C19—C23—Fe169.1 (9)
C12A—C13—H13B73.6C22—C23—Fe173.0 (8)
C12—C13—H13B110.2C19—C23—H23123.8
N9C—C13—H13B110.2C22—C23—H23123.8
H13A—C13—H13B108.5Fe1—C23—H23125.7
C5A—C9A—C9118.8 (2)C22A—C21A—C20A105.0 (15)
C5A—C9A—C9B119.3 (2)C22A—C21A—Fe165.5 (9)
C9—C9A—C9B121.9 (2)C20A—C21A—Fe167.6 (13)
C8—C9—C9A121.0 (2)C22A—C21A—H21A127.5
C8—C9—H9119.5C20A—C21A—H21A127.5
C9A—C9—H9119.5Fe1—C21A—H21A130.8
C9—C8—C7119.6 (3)C21A—C22A—C23A112.4 (14)
C9—C8—H8120.2C21A—C22A—Fe172.5 (10)
C7—C8—H8120.2C23A—C22A—Fe170.8 (15)
C6—C7—C8120.8 (3)C21A—C22A—H22A123.8
C6—C7—H7119.6C23A—C22A—H22A123.8
C8—C7—H7119.6Fe1—C22A—H22A124.4
C7—C6—C5A119.5 (3)C21A—C20A—C19A107.4 (17)
C7—C6—H6120.2C21A—C20A—Fe170.9 (12)
C5A—C6—H6120.2C19A—C20A—Fe173.9 (16)
C9A—C5A—C6120.4 (2)C21A—C20A—H20A126.3
C9A—C5A—N5120.8 (2)C19A—C20A—H20A126.3
C6—C5A—N5118.9 (2)Fe1—C20A—H20A120.8
O3—C4—N5121.8 (2)C20A—C19A—C23A110.3 (18)
O3—C4—C3A121.3 (2)C20A—C19A—Fe165.5 (15)
N5—C4—C3A116.9 (2)C23A—C19A—Fe165.7 (17)
C13—N9C—C9B118.8 (2)C20A—C19A—H19A124.9
C13—N9C—C10A106.1 (2)C23A—C19A—H19A124.9
C9B—N9C—C10A107.79 (18)Fe1—C19A—H19A136.3
C4—N5—C5A125.5 (2)C22A—C23A—C19A103.2 (15)
C4—N5—H5A117.3C22A—C23A—Fe166.7 (12)
C5A—N5—H5A117.3C19A—C23A—Fe173.7 (17)
C1—O2—C3110.79 (17)C22A—C23A—H23A128.4
C19—Fe1—C22A66.9 (5)C19A—C23A—H23A128.4
C19—Fe1—C2039.5 (5)Fe1—C23A—H23A123.0
C22A—Fe1—C2054.1 (5)
C18—C14—C15—C160.0 (3)C20A—Fe1—C19—C20−27.8 (10)
C3—C14—C15—C16−178.4 (2)C15—Fe1—C19—C20−110.1 (8)
Fe1—C14—C15—C1659.68 (19)C14—Fe1—C19—C20−154.2 (7)
C18—C14—C15—Fe1−59.70 (18)C23A—Fe1—C19—C20106.3 (12)
C3—C14—C15—Fe1122.0 (3)C16—Fe1—C19—C20−69.5 (9)
C14—C15—C16—C170.1 (3)C21—Fe1—C19—C2037.8 (6)
Fe1—C15—C16—C1759.9 (2)C18—Fe1—C19—C20168.2 (7)
C14—C15—C16—Fe1−59.85 (19)C23—C19—C20—C214.3 (17)
C15—C16—C17—C18−0.1 (3)Fe1—C19—C20—C21−59.7 (8)
Fe1—C16—C17—C1858.81 (19)C23—C19—C20—Fe164.0 (13)
C15—C16—C17—Fe1−58.9 (2)C22A—Fe1—C20—C19−96.6 (8)
C16—C17—C18—C140.1 (3)C23—Fe1—C20—C19−37.5 (6)
Fe1—C17—C18—C1458.84 (18)C20A—Fe1—C20—C1958 (3)
C16—C17—C18—Fe1−58.7 (2)C15—Fe1—C20—C1988.4 (7)
C15—C14—C18—C17−0.1 (3)C14—Fe1—C20—C1948.3 (10)
C3—C14—C18—C17178.4 (2)C23A—Fe1—C20—C19−48.9 (9)
Fe1—C14—C18—C17−59.51 (19)C16—Fe1—C20—C19134.0 (7)
C15—C14—C18—Fe159.45 (18)C21—Fe1—C20—C19−119.3 (8)
C3—C14—C18—Fe1−122.1 (2)C17—Fe1—C20—C19175.3 (6)
C15—C14—C3—O2−37.1 (4)C19—Fe1—C20—C21119.3 (8)
C18—C14—C3—O2144.9 (2)C22A—Fe1—C20—C2122.7 (7)
Fe1—C14—C3—O255.3 (3)C23—Fe1—C20—C2181.8 (6)
C15—C14—C3—C3A81.3 (3)C20A—Fe1—C20—C21178 (3)
C18—C14—C3—C3A−96.8 (3)C15—Fe1—C20—C21−152.3 (5)
Fe1—C14—C3—C3A173.62 (16)C14—Fe1—C20—C21167.6 (6)
O2—C3—C3A—C4−154.81 (18)C23A—Fe1—C20—C2170.4 (8)
C14—C3—C3A—C483.1 (3)C16—Fe1—C20—C21−106.7 (5)
O2—C3—C3A—C1076.9 (2)C17—Fe1—C20—C21−65.4 (6)
C14—C3—C3A—C10−45.2 (3)C19—C20—C21—C22−3.9 (16)
O2—C3—C3A—C9B−32.7 (2)Fe1—C20—C21—C22−62.4 (10)
C14—C3—C3A—C9B−154.8 (2)C19—C20—C21—Fe158.5 (10)
C4—C3A—C9B—N9C−96.0 (2)C19—Fe1—C21—C20−37.0 (5)
C10—C3A—C9B—N9C26.7 (2)C22A—Fe1—C21—C20−121.2 (14)
C3—C3A—C9B—N9C145.68 (18)C23—Fe1—C21—C20−78.6 (7)
C4—C3A—C9B—C9A35.1 (3)C20A—Fe1—C21—C20−0.9 (12)
C10—C3A—C9B—C9A157.72 (19)C15—Fe1—C21—C2055.2 (8)
C3—C3A—C9B—C9A−83.3 (2)C14—Fe1—C21—C20−145.3 (14)
C4—C3A—C9B—C1148.9 (2)C23A—Fe1—C21—C20−87.8 (10)
C10—C3A—C9B—C1−88.4 (2)C16—Fe1—C21—C2093.1 (6)
C3—C3A—C9B—C130.6 (2)C18—Fe1—C21—C20176.6 (5)
N9C—C9B—C1—O147.7 (3)C17—Fe1—C21—C20136.1 (6)
C9A—C9B—C1—O1−79.7 (3)C19—Fe1—C21—C2279.6 (9)
C3A—C9B—C1—O1161.5 (2)C22A—Fe1—C21—C22−4.6 (13)
N9C—C9B—C1—O2−133.0 (2)C20—Fe1—C21—C22116.6 (10)
C9A—C9B—C1—O299.6 (2)C23—Fe1—C21—C2238.0 (9)
C3A—C9B—C1—O2−19.2 (2)C20A—Fe1—C21—C22115.7 (12)
C4—C3A—C10—C10A89.9 (2)C15—Fe1—C21—C22171.7 (6)
C9B—C3A—C10—C10A−33.7 (2)C14—Fe1—C21—C22−29 (2)
C3—C3A—C10—C10A−143.8 (2)C23A—Fe1—C21—C2228.8 (10)
C3A—C10—C10A—N9C29.6 (2)C16—Fe1—C21—C22−150.3 (8)
C3A—C10—C10A—C11−88.2 (3)C18—Fe1—C21—C22−66.8 (9)
N9C—C10A—C11—C12−3.7 (4)C17—Fe1—C21—C22−107.3 (8)
C10—C10A—C11—C12114.2 (4)C20—C21—C22—C232.0 (17)
N9C—C10A—C11—C12A32.8 (7)Fe1—C21—C22—C23−58.7 (11)
C10—C10A—C11—C12A150.8 (7)C20—C21—C22—Fe160.7 (8)
C10A—C11—C12—C1322.7 (5)C19—Fe1—C22—C2334.4 (9)
C12A—C11—C12—C13−62.6 (8)C22A—Fe1—C22—C23122 (2)
C10A—C11—C12A—C13−38.1 (10)C20—Fe1—C22—C2377.7 (9)
C12—C11—C12A—C1364.5 (9)C20A—Fe1—C22—C2366.1 (11)
C11—C12A—C13—C12−64.6 (9)C15—Fe1—C22—C23−42 (3)
C11—C12A—C13—N9C30.2 (11)C14—Fe1—C22—C23−70.2 (11)
C11—C12—C13—C12A64.6 (8)C23A—Fe1—C22—C23−4(2)
C11—C12—C13—N9C−34.1 (5)C16—Fe1—C22—C23173.7 (6)
N9C—C9B—C9A—C5A106.3 (2)C21—Fe1—C22—C23116.8 (14)
C1—C9B—C9A—C5A−130.4 (2)C18—Fe1—C22—C23−110.3 (9)
C3A—C9B—C9A—C5A−20.4 (3)C17—Fe1—C22—C23−153.0 (8)
N9C—C9B—C9A—C9−71.7 (3)C19—Fe1—C22—C21−82.4 (9)
C1—C9B—C9A—C951.6 (3)C22A—Fe1—C22—C215.2 (14)
C3A—C9B—C9A—C9161.7 (2)C20—Fe1—C22—C21−39.1 (8)
C5A—C9A—C9—C81.7 (4)C23—Fe1—C22—C21−116.8 (14)
C9B—C9A—C9—C8179.6 (2)C20A—Fe1—C22—C21−50.8 (10)
C9A—C9—C8—C70.0 (4)C15—Fe1—C22—C21−158.8 (15)
C9—C8—C7—C6−1.2 (4)C14—Fe1—C22—C21172.9 (6)
C8—C7—C6—C5A0.7 (4)C23A—Fe1—C22—C21−121 (2)
C9—C9A—C5A—C6−2.1 (4)C16—Fe1—C22—C2156.9 (13)
C9B—C9A—C5A—C6179.8 (2)C18—Fe1—C22—C21132.9 (8)
C9—C9A—C5A—N5177.2 (2)C17—Fe1—C22—C2190.1 (9)
C9B—C9A—C5A—N5−0.8 (3)C20—C19—C23—C22−3(2)
C7—C6—C5A—C9A1.0 (4)Fe1—C19—C23—C2260.3 (13)
C7—C6—C5A—N5−178.4 (2)C20—C19—C23—Fe1−63.4 (11)
C10—C3A—C4—O335.8 (3)C21—C22—C23—C191(2)
C9B—C3A—C4—O3152.1 (2)Fe1—C22—C23—C19−58.0 (13)
C3—C3A—C4—O3−93.3 (3)C21—C22—C23—Fe158.7 (10)
C10—C3A—C4—N5−146.5 (2)C22A—Fe1—C23—C19102.2 (12)
C9B—C3A—C4—N5−30.3 (3)C20—Fe1—C23—C1938.9 (8)
C3—C3A—C4—N584.3 (3)C20A—Fe1—C23—C1920.0 (10)
C12A—C13—N9C—C9B−130.2 (8)C15—Fe1—C23—C19−67.4 (10)
C12—C13—N9C—C9B−89.0 (4)C14—Fe1—C23—C19−107.4 (9)
C12A—C13—N9C—C10A−8.7 (8)C23A—Fe1—C23—C19133 (7)
C12—C13—N9C—C10A32.5 (4)C21—Fe1—C23—C1983.7 (9)
C9A—C9B—N9C—C13−17.6 (3)C18—Fe1—C23—C19−151.4 (8)
C1—C9B—N9C—C13−139.4 (2)C17—Fe1—C23—C19172.4 (8)
C3A—C9B—N9C—C13111.7 (2)C19—Fe1—C23—C22−122.9 (13)
C9A—C9B—N9C—C10A−138.3 (2)C22A—Fe1—C23—C22−20.7 (9)
C1—C9B—N9C—C10A99.9 (2)C20—Fe1—C23—C22−84.0 (9)
C3A—C9B—N9C—C10A−9.0 (2)C20A—Fe1—C23—C22−102.9 (10)
C10—C10A—N9C—C13−141.1 (2)C15—Fe1—C23—C22169.8 (7)
C11—C10A—N9C—C13−16.5 (3)C14—Fe1—C23—C22129.7 (8)
C10—C10A—N9C—C9B−12.8 (2)C23A—Fe1—C23—C2210 (6)
C11—C10A—N9C—C9B111.7 (2)C21—Fe1—C23—C22−39.2 (8)
O3—C4—N5—C5A−173.3 (2)C18—Fe1—C23—C2285.8 (9)
C3A—C4—N5—C5A9.0 (4)C17—Fe1—C23—C2249.5 (13)
C9A—C5A—N5—C47.5 (4)C19—Fe1—C21A—C22A85.7 (10)
C6—C5A—N5—C4−173.1 (2)C20—Fe1—C21A—C22A107.9 (19)
O1—C1—O2—C3177.8 (2)C23—Fe1—C21A—C22A47.2 (9)
C9B—C1—O2—C3−1.6 (3)C20A—Fe1—C21A—C22A119.6 (15)
C14—C3—O2—C1147.5 (2)C15—Fe1—C21A—C22A−179.8 (7)
C3A—C3—O2—C121.8 (2)C14—Fe1—C21A—C22A166 (3)
C14—C15—Fe1—C19−106.0 (5)C23A—Fe1—C21A—C22A36.9 (9)
C16—C15—Fe1—C19135.6 (5)C16—Fe1—C21A—C22A−141.3 (9)
C14—C15—Fe1—C20−148.8 (4)C21—Fe1—C21A—C22A−13.2 (14)
C16—C15—Fe1—C2092.8 (5)C18—Fe1—C21A—C22A−68.4 (14)
C14—C15—Fe1—C23−68.6 (6)C17—Fe1—C21A—C22A−99.6 (9)
C16—C15—Fe1—C23173.1 (6)C19—Fe1—C21A—C20A−34.0 (13)
C14—C15—Fe1—C20A−139.9 (9)C22A—Fe1—C21A—C20A−119.6 (15)
C16—C15—Fe1—C20A101.7 (9)C20—Fe1—C21A—C20A−11.7 (17)
C16—C15—Fe1—C14−118.3 (2)C23—Fe1—C21A—C20A−72.5 (13)
C14—C15—Fe1—C23A−62.8 (13)C15—Fe1—C21A—C20A60.6 (15)
C16—C15—Fe1—C23A178.9 (13)C14—Fe1—C21A—C20A46 (4)
C14—C15—Fe1—C16118.3 (2)C23A—Fe1—C21A—C20A−82.7 (12)
C14—C15—Fe1—C21173.9 (6)C16—Fe1—C21A—C20A99.0 (14)
C16—C15—Fe1—C2155.6 (7)C21—Fe1—C21A—C20A−133 (2)
C14—C15—Fe1—C1838.06 (15)C18—Fe1—C21A—C20A171.9 (11)
C16—C15—Fe1—C18−80.28 (19)C17—Fe1—C21A—C20A140.8 (13)
C14—C15—Fe1—C1781.59 (17)C20A—C21A—C22A—C23A−4(3)
C16—C15—Fe1—C17−36.75 (18)Fe1—C21A—C22A—C23A−59.9 (19)
C15—C14—Fe1—C1992.1 (5)C20A—C21A—C22A—Fe156.3 (15)
C18—C14—Fe1—C19−149.0 (5)C19—Fe1—C22A—C21A−73.4 (10)
C3—C14—Fe1—C19−31.1 (5)C20—Fe1—C22A—C21A−29.9 (10)
C15—C14—Fe1—C22A179.2 (8)C23—Fe1—C22A—C21A−114.3 (12)
C18—C14—Fe1—C22A−62.0 (8)C20A—Fe1—C22A—C21A−37.7 (9)
C3—C14—Fe1—C22A56.0 (8)C14—Fe1—C22A—C21A−175.4 (8)
C15—C14—Fe1—C2060.3 (6)C23A—Fe1—C22A—C21A−122.2 (16)
C18—C14—Fe1—C20179.1 (6)C16—Fe1—C22A—C21A57.6 (11)
C3—C14—Fe1—C20−62.9 (7)C21—Fe1—C22A—C21A13.3 (12)
C15—C14—Fe1—C23132.9 (5)C18—Fe1—C22A—C21A143.5 (9)
C18—C14—Fe1—C23−108.3 (5)C17—Fe1—C22A—C21A98.9 (10)
C3—C14—Fe1—C239.7 (5)C19—Fe1—C22A—C23A48.8 (13)
C15—C14—Fe1—C20A56.3 (10)C20—Fe1—C22A—C23A92.3 (13)
C18—C14—Fe1—C20A175.1 (10)C23—Fe1—C22A—C23A7.9 (15)
C3—C14—Fe1—C20A−66.9 (10)C20A—Fe1—C22A—C23A84.4 (12)
C18—C14—Fe1—C15118.8 (2)C14—Fe1—C22A—C23A−53.2 (16)
C3—C14—Fe1—C15−123.2 (3)C16—Fe1—C22A—C23A179.8 (12)
C15—C14—Fe1—C23A142.8 (8)C21—Fe1—C22A—C23A135.5 (19)
C18—C14—Fe1—C23A−98.4 (8)C18—Fe1—C22A—C23A−94.3 (13)
C3—C14—Fe1—C23A19.6 (9)C17—Fe1—C22A—C23A−138.9 (13)
C15—C14—Fe1—C16−38.58 (18)C22A—C21A—C20A—C19A10 (3)
C18—C14—Fe1—C1680.26 (19)Fe1—C21A—C20A—C19A65 (2)
C3—C14—Fe1—C16−161.8 (3)C22A—C21A—C20A—Fe1−54.9 (13)
C15—C14—Fe1—C21−164.6 (14)C19—Fe1—C20A—C21A115.8 (17)
C18—C14—Fe1—C21−45.7 (14)C22A—Fe1—C20A—C21A38.1 (9)
C3—C14—Fe1—C2172.3 (14)C20—Fe1—C20A—C21A17 (2)
C15—C14—Fe1—C18−118.8 (2)C23—Fe1—C20A—C21A93.2 (13)
C3—C14—Fe1—C18118.0 (3)C15—Fe1—C20A—C21A−136.4 (14)
C15—C14—Fe1—C17−81.68 (18)C14—Fe1—C20A—C21A−170.2 (12)
C18—C14—Fe1—C1737.16 (18)C23A—Fe1—C20A—C21A83.1 (11)
C3—C14—Fe1—C17155.1 (3)C16—Fe1—C20A—C21A−93.8 (14)
C17—C16—Fe1—C19172.7 (7)C21—Fe1—C20A—C21A18.6 (11)
C15—C16—Fe1—C19−67.5 (7)C17—Fe1—C20A—C21A−64.2 (15)
C17—C16—Fe1—C22A71.0 (10)C19—Fe1—C20A—C19A0.4 (17)
C15—C16—Fe1—C22A−169.1 (9)C22A—Fe1—C20A—C19A−77.3 (13)
C17—C16—Fe1—C20132.4 (5)C20—Fe1—C20A—C19A−99 (3)
C15—C16—Fe1—C20−107.7 (5)C23—Fe1—C20A—C19A−22.3 (14)
C17—C16—Fe1—C20A150.2 (8)C15—Fe1—C20A—C19A108.2 (14)
C15—C16—Fe1—C20A−89.9 (8)C14—Fe1—C20A—C19A74.3 (16)
C17—C16—Fe1—C15−119.9 (2)C23A—Fe1—C20A—C19A−32.4 (12)
C17—C16—Fe1—C14−81.80 (18)C16—Fe1—C20A—C19A150.8 (14)
C15—C16—Fe1—C1438.09 (16)C21—Fe1—C20A—C19A−96.9 (14)
C17—C16—Fe1—C2187.8 (5)C17—Fe1—C20A—C19A−179.7 (11)
C15—C16—Fe1—C21−152.3 (5)C21A—C20A—C19A—C23A−14 (3)
C17—C16—Fe1—C18−37.58 (16)Fe1—C20A—C19A—C23A49 (2)
C15—C16—Fe1—C1882.31 (18)C21A—C20A—C19A—Fe1−63.4 (17)
C15—C16—Fe1—C17119.9 (2)C19—Fe1—C19A—C20A−2(7)
C17—C18—Fe1—C19176.9 (7)C22A—Fe1—C19A—C20A86.0 (13)
C14—C18—Fe1—C1957.1 (7)C20—Fe1—C19A—C20A24.4 (10)
C17—C18—Fe1—C22A−92.5 (9)C23—Fe1—C19A—C20A139 (2)
C14—C18—Fe1—C22A147.7 (9)C15—Fe1—C19A—C20A−84.8 (15)
C17—C18—Fe1—C23−150.7 (5)C14—Fe1—C19A—C20A−128.7 (13)
C14—C18—Fe1—C2389.5 (5)C23A—Fe1—C19A—C20A129 (2)
C17—C18—Fe1—C1581.9 (2)C16—Fe1—C19A—C20A−47 (2)
C14—C18—Fe1—C15−37.91 (15)C21—Fe1—C19A—C20A63.3 (12)
C17—C18—Fe1—C14119.8 (3)C18—Fe1—C19A—C20A−166.5 (10)
C17—C18—Fe1—C23A−139.7 (8)C19—Fe1—C19A—C23A−130 (9)
C14—C18—Fe1—C23A100.5 (8)C22A—Fe1—C19A—C23A−42.6 (12)
C17—C18—Fe1—C1637.23 (18)C20—Fe1—C19A—C23A−104.3 (17)
C14—C18—Fe1—C16−82.55 (18)C23—Fe1—C19A—C23A10.2 (17)
C17—C18—Fe1—C21−71.0 (5)C20A—Fe1—C19A—C23A−129 (2)
C14—C18—Fe1—C21169.3 (4)C15—Fe1—C19A—C23A146.6 (14)
C14—C18—Fe1—C17−119.8 (3)C14—Fe1—C19A—C23A102.6 (15)
C16—C17—Fe1—C22A−133.0 (10)C16—Fe1—C19A—C23A−175.5 (12)
C18—C17—Fe1—C22A107.6 (10)C21—Fe1—C19A—C23A−65.3 (13)
C16—C17—Fe1—C20−71.5 (6)C18—Fe1—C19A—C23A64.9 (19)
C18—C17—Fe1—C20169.1 (6)C21A—C22A—C23A—C19A−5(3)
C16—C17—Fe1—C23174.4 (8)Fe1—C22A—C23A—C19A−65 (2)
C18—C17—Fe1—C2354.9 (8)C21A—C22A—C23A—Fe160.9 (15)
C16—C17—Fe1—C20A−47.1 (10)C20A—C19A—C23A—C22A11 (4)
C18—C17—Fe1—C20A−166.5 (10)Fe1—C19A—C23A—C22A60.5 (18)
C16—C17—Fe1—C1537.89 (17)C20A—C19A—C23A—Fe1−49 (2)
C18—C17—Fe1—C15−81.52 (18)C19—Fe1—C23A—C22A−104.7 (16)
C16—C17—Fe1—C1481.79 (18)C20—Fe1—C23A—C22A−62.6 (11)
C18—C17—Fe1—C14−37.62 (16)C23—Fe1—C23A—C22A−144 (7)
C16—C17—Fe1—C23A−175.5 (12)C20A—Fe1—C23A—C22A−80.3 (11)
C18—C17—Fe1—C23A65.0 (12)C15—Fe1—C23A—C22A−168.4 (11)
C18—C17—Fe1—C16−119.4 (3)C14—Fe1—C23A—C22A152.1 (12)
C16—C17—Fe1—C21−110.2 (5)C21—Fe1—C23A—C22A−17.3 (8)
C18—C17—Fe1—C21130.4 (5)C18—Fe1—C23A—C22A107.3 (13)
C16—C17—Fe1—C18119.4 (3)C17—Fe1—C23A—C22A67.5 (16)
C22A—Fe1—C19—C23−55.9 (11)C19—Fe1—C23A—C19A7.9 (17)
C20—Fe1—C19—C23−117.0 (11)C22A—Fe1—C23A—C19A112.6 (19)
C20A—Fe1—C19—C23−144.8 (16)C20—Fe1—C23A—C19A50.0 (14)
C15—Fe1—C19—C23133.0 (8)C23—Fe1—C23A—C19A−31 (6)
C14—Fe1—C19—C2388.8 (9)C20A—Fe1—C23A—C19A32.4 (12)
C23A—Fe1—C19—C23−10.7 (14)C15—Fe1—C23A—C19A−56 (2)
C16—Fe1—C19—C23173.5 (7)C14—Fe1—C23A—C19A−95.2 (15)
C21—Fe1—C19—C23−79.2 (8)C21—Fe1—C23A—C19A95.3 (15)
C18—Fe1—C19—C2351.2 (12)C18—Fe1—C23A—C19A−140.1 (14)
C22A—Fe1—C19—C2061.1 (8)C17—Fe1—C23A—C19A−179.9 (12)
C23—Fe1—C19—C20117.0 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10B···O30.972.472.877 (3)105
C9—H9···O10.932.583.128 (3)118
C10A—H10C···O1i0.982.563.371 (3)140
N5—H5A···O3ii0.861.992.840 (3)168

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2240).

References

  • Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem.689, 4678–4682.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem.21, 613–625.
  • Gunasekaran, B., Kathiravan, S., Raghunathan, R. & Manivannan, V. (2009). Acta Cryst. E65, m1673. [PMC free article] [PubMed]
  • Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem.11, 2505–2517. [PubMed]
  • Kamala, E. T. S., Nirmala, S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, m687–m688. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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