metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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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

aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, bDepartment of Organic Chemistry, University of Madras, Guindy campus, Chennai 600 025, India, and cDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: crystallography2010@gmail.com

(Received 19 October 2010; accepted 5 November 2010; online 10 November 2010)

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[Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.]); Jaouen et al. (2004[Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.]); Biot et al. (2004[Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678-4682.]). For related structures, see: Kamala et al. (2009[Kamala, E. T. S., Nirmala, S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, m687-m688.]); Gunasekaran et al. (2009[Gunasekaran, B., Kathiravan, S., Raghunathan, R. & Manivannan, V. (2009). Acta Cryst. E65, m1673.]);

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C21H19N2O3)]

  • Mr = 468.32

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.864, Tmax = 0.867

  • 20500 measured reflections

  • 5308 independent reflections

  • 3322 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10B⋯O3 0.97 2.47 2.877 (3) 105
C9—H9⋯O1 0.93 2.58 3.128 (3) 118
C10A—H10C⋯O1i 0.98 2.56 3.371 (3) 140
N5—H5A⋯O3ii 0.86 1.99 2.840 (3) 168
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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.

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

Computing details top

Data collection: APEX2 (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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Crystal structure of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.
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 top
Crystal data top
[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 top
Bruker Kappa APEXII CCD
diffractometer
5308 independent reflections
Radiation source: fine-focus sealed tube3322 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 0 pixels mm-1θmax = 28.3°, θmin = 2.0°
ω and φ scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2524
Tmin = 0.864, Tmax = 0.867l = 1515
20500 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.01 w = 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 = 0.25 e Å3
Crystal data top
[Fe(C5H5)(C21H19N2O3)]V = 2151.0 (3) Å3
Mr = 468.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.6486 (7) ŵ = 0.73 mm1
b = 18.8900 (13) ÅT = 295 K
c = 11.8207 (9) Å0.20 × 0.20 × 0.20 mm
β = 93.248 (5)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5308 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3322 reflections with I > 2σ(I)
Tmin = 0.864, Tmax = 0.867Rint = 0.042
20500 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0445 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.01Δρmax = 0.46 e Å3
5308 reflectionsΔρmin = 0.25 e Å3
344 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H30.53010.20930.06270.047*
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)
H12A0.99070.00020.15240.089*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)
H13A1.00050.08760.00070.089*
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)
H90.96710.19760.15760.055*
C80.9081 (3)0.13042 (15)0.2823 (2)0.0558 (7)
H80.97460.14400.33190.067*
C70.8138 (3)0.07823 (15)0.3128 (2)0.0599 (8)
H70.81590.05720.38380.072*
C60.7164 (3)0.05681 (14)0.2394 (2)0.0545 (7)
H60.65370.02110.26030.065*
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)
H5A0.56700.02830.07750.057*
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)
H190.49500.42480.02740.089*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)
H220.15610.32940.15830.074*0.64 (2)
C230.3532 (15)0.3686 (8)0.1174 (12)0.069 (5)0.64 (2)
H230.40720.34640.16950.083*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)
H22A0.10270.35980.09590.068*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)
H19A0.50550.41890.08490.099*0.36 (2)
C23A0.317 (3)0.3643 (17)0.125 (2)0.082 (10)0.36 (2)
H23A0.33180.33340.18410.098*0.36 (2)
Atomic displacement parameters (Å2) top
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, º) top
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—C2027.8 (10)
C3—C14—C15—C16178.4 (2)C15—Fe1—C19—C20110.1 (8)
Fe1—C14—C15—C1659.68 (19)C14—Fe1—C19—C20154.2 (7)
C18—C14—C15—Fe159.70 (18)C23A—Fe1—C19—C20106.3 (12)
C3—C14—C15—Fe1122.0 (3)C16—Fe1—C19—C2069.5 (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—Fe159.85 (19)C23—C19—C20—C214.3 (17)
C15—C16—C17—C180.1 (3)Fe1—C19—C20—C2159.7 (8)
Fe1—C16—C17—C1858.81 (19)C23—C19—C20—Fe164.0 (13)
C15—C16—C17—Fe158.9 (2)C22A—Fe1—C20—C1996.6 (8)
C16—C17—C18—C140.1 (3)C23—Fe1—C20—C1937.5 (6)
Fe1—C17—C18—C1458.84 (18)C20A—Fe1—C20—C1958 (3)
C16—C17—C18—Fe158.7 (2)C15—Fe1—C20—C1988.4 (7)
C15—C14—C18—C170.1 (3)C14—Fe1—C20—C1948.3 (10)
C3—C14—C18—C17178.4 (2)C23A—Fe1—C20—C1948.9 (9)
Fe1—C14—C18—C1759.51 (19)C16—Fe1—C20—C19134.0 (7)
C15—C14—C18—Fe159.45 (18)C21—Fe1—C20—C19119.3 (8)
C3—C14—C18—Fe1122.1 (2)C17—Fe1—C20—C19175.3 (6)
C15—C14—C3—O237.1 (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—C3A96.8 (3)C15—Fe1—C20—C21152.3 (5)
Fe1—C14—C3—C3A173.62 (16)C14—Fe1—C20—C21167.6 (6)
O2—C3—C3A—C4154.81 (18)C23A—Fe1—C20—C2170.4 (8)
C14—C3—C3A—C483.1 (3)C16—Fe1—C20—C21106.7 (5)
O2—C3—C3A—C1076.9 (2)C17—Fe1—C20—C2165.4 (6)
C14—C3—C3A—C1045.2 (3)C19—C20—C21—C223.9 (16)
O2—C3—C3A—C9B32.7 (2)Fe1—C20—C21—C2262.4 (10)
C14—C3—C3A—C9B154.8 (2)C19—C20—C21—Fe158.5 (10)
C4—C3A—C9B—N9C96.0 (2)C19—Fe1—C21—C2037.0 (5)
C10—C3A—C9B—N9C26.7 (2)C22A—Fe1—C21—C20121.2 (14)
C3—C3A—C9B—N9C145.68 (18)C23—Fe1—C21—C2078.6 (7)
C4—C3A—C9B—C9A35.1 (3)C20A—Fe1—C21—C200.9 (12)
C10—C3A—C9B—C9A157.72 (19)C15—Fe1—C21—C2055.2 (8)
C3—C3A—C9B—C9A83.3 (2)C14—Fe1—C21—C20145.3 (14)
C4—C3A—C9B—C1148.9 (2)C23A—Fe1—C21—C2087.8 (10)
C10—C3A—C9B—C188.4 (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—O179.7 (3)C19—Fe1—C21—C2279.6 (9)
C3A—C9B—C1—O1161.5 (2)C22A—Fe1—C21—C224.6 (13)
N9C—C9B—C1—O2133.0 (2)C20—Fe1—C21—C22116.6 (10)
C9A—C9B—C1—O299.6 (2)C23—Fe1—C21—C2238.0 (9)
C3A—C9B—C1—O219.2 (2)C20A—Fe1—C21—C22115.7 (12)
C4—C3A—C10—C10A89.9 (2)C15—Fe1—C21—C22171.7 (6)
C9B—C3A—C10—C10A33.7 (2)C14—Fe1—C21—C2229 (2)
C3—C3A—C10—C10A143.8 (2)C23A—Fe1—C21—C2228.8 (10)
C3A—C10—C10A—N9C29.6 (2)C16—Fe1—C21—C22150.3 (8)
C3A—C10—C10A—C1188.2 (3)C18—Fe1—C21—C2266.8 (9)
N9C—C10A—C11—C123.7 (4)C17—Fe1—C21—C22107.3 (8)
C10—C10A—C11—C12114.2 (4)C20—C21—C22—C232.0 (17)
N9C—C10A—C11—C12A32.8 (7)Fe1—C21—C22—C2358.7 (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—C1362.6 (8)C22A—Fe1—C22—C23122 (2)
C10A—C11—C12A—C1338.1 (10)C20—Fe1—C22—C2377.7 (9)
C12—C11—C12A—C1364.5 (9)C20A—Fe1—C22—C2366.1 (11)
C11—C12A—C13—C1264.6 (9)C15—Fe1—C22—C2342 (3)
C11—C12A—C13—N9C30.2 (11)C14—Fe1—C22—C2370.2 (11)
C11—C12—C13—C12A64.6 (8)C23A—Fe1—C22—C234 (2)
C11—C12—C13—N9C34.1 (5)C16—Fe1—C22—C23173.7 (6)
N9C—C9B—C9A—C5A106.3 (2)C21—Fe1—C22—C23116.8 (14)
C1—C9B—C9A—C5A130.4 (2)C18—Fe1—C22—C23110.3 (9)
C3A—C9B—C9A—C5A20.4 (3)C17—Fe1—C22—C23153.0 (8)
N9C—C9B—C9A—C971.7 (3)C19—Fe1—C22—C2182.4 (9)
C1—C9B—C9A—C951.6 (3)C22A—Fe1—C22—C215.2 (14)
C3A—C9B—C9A—C9161.7 (2)C20—Fe1—C22—C2139.1 (8)
C5A—C9A—C9—C81.7 (4)C23—Fe1—C22—C21116.8 (14)
C9B—C9A—C9—C8179.6 (2)C20A—Fe1—C22—C2150.8 (10)
C9A—C9—C8—C70.0 (4)C15—Fe1—C22—C21158.8 (15)
C9—C8—C7—C61.2 (4)C14—Fe1—C22—C21172.9 (6)
C8—C7—C6—C5A0.7 (4)C23A—Fe1—C22—C21121 (2)
C9—C9A—C5A—C62.1 (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—N50.8 (3)C20—C19—C23—C223 (2)
C7—C6—C5A—C9A1.0 (4)Fe1—C19—C23—C2260.3 (13)
C7—C6—C5A—N5178.4 (2)C20—C19—C23—Fe163.4 (11)
C10—C3A—C4—O335.8 (3)C21—C22—C23—C191 (2)
C9B—C3A—C4—O3152.1 (2)Fe1—C22—C23—C1958.0 (13)
C3—C3A—C4—O393.3 (3)C21—C22—C23—Fe158.7 (10)
C10—C3A—C4—N5146.5 (2)C22A—Fe1—C23—C19102.2 (12)
C9B—C3A—C4—N530.3 (3)C20—Fe1—C23—C1938.9 (8)
C3—C3A—C4—N584.3 (3)C20A—Fe1—C23—C1920.0 (10)
C12A—C13—N9C—C9B130.2 (8)C15—Fe1—C23—C1967.4 (10)
C12—C13—N9C—C9B89.0 (4)C14—Fe1—C23—C19107.4 (9)
C12A—C13—N9C—C10A8.7 (8)C23A—Fe1—C23—C19133 (7)
C12—C13—N9C—C10A32.5 (4)C21—Fe1—C23—C1983.7 (9)
C9A—C9B—N9C—C1317.6 (3)C18—Fe1—C23—C19151.4 (8)
C1—C9B—N9C—C13139.4 (2)C17—Fe1—C23—C19172.4 (8)
C3A—C9B—N9C—C13111.7 (2)C19—Fe1—C23—C22122.9 (13)
C9A—C9B—N9C—C10A138.3 (2)C22A—Fe1—C23—C2220.7 (9)
C1—C9B—N9C—C10A99.9 (2)C20—Fe1—C23—C2284.0 (9)
C3A—C9B—N9C—C10A9.0 (2)C20A—Fe1—C23—C22102.9 (10)
C10—C10A—N9C—C13141.1 (2)C15—Fe1—C23—C22169.8 (7)
C11—C10A—N9C—C1316.5 (3)C14—Fe1—C23—C22129.7 (8)
C10—C10A—N9C—C9B12.8 (2)C23A—Fe1—C23—C2210 (6)
C11—C10A—N9C—C9B111.7 (2)C21—Fe1—C23—C2239.2 (8)
O3—C4—N5—C5A173.3 (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—C4173.1 (2)C20—Fe1—C21A—C22A107.9 (19)
O1—C1—O2—C3177.8 (2)C23—Fe1—C21A—C22A47.2 (9)
C9B—C1—O2—C31.6 (3)C20A—Fe1—C21A—C22A119.6 (15)
C14—C3—O2—C1147.5 (2)C15—Fe1—C21A—C22A179.8 (7)
C3A—C3—O2—C121.8 (2)C14—Fe1—C21A—C22A166 (3)
C14—C15—Fe1—C19106.0 (5)C23A—Fe1—C21A—C22A36.9 (9)
C16—C15—Fe1—C19135.6 (5)C16—Fe1—C21A—C22A141.3 (9)
C14—C15—Fe1—C20148.8 (4)C21—Fe1—C21A—C22A13.2 (14)
C16—C15—Fe1—C2092.8 (5)C18—Fe1—C21A—C22A68.4 (14)
C14—C15—Fe1—C2368.6 (6)C17—Fe1—C21A—C22A99.6 (9)
C16—C15—Fe1—C23173.1 (6)C19—Fe1—C21A—C20A34.0 (13)
C14—C15—Fe1—C20A139.9 (9)C22A—Fe1—C21A—C20A119.6 (15)
C16—C15—Fe1—C20A101.7 (9)C20—Fe1—C21A—C20A11.7 (17)
C16—C15—Fe1—C14118.3 (2)C23—Fe1—C21A—C20A72.5 (13)
C14—C15—Fe1—C23A62.8 (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—C20A82.7 (12)
C14—C15—Fe1—C21173.9 (6)C16—Fe1—C21A—C20A99.0 (14)
C16—C15—Fe1—C2155.6 (7)C21—Fe1—C21A—C20A133 (2)
C14—C15—Fe1—C1838.06 (15)C18—Fe1—C21A—C20A171.9 (11)
C16—C15—Fe1—C1880.28 (19)C17—Fe1—C21A—C20A140.8 (13)
C14—C15—Fe1—C1781.59 (17)C20A—C21A—C22A—C23A4 (3)
C16—C15—Fe1—C1736.75 (18)Fe1—C21A—C22A—C23A59.9 (19)
C15—C14—Fe1—C1992.1 (5)C20A—C21A—C22A—Fe156.3 (15)
C18—C14—Fe1—C19149.0 (5)C19—Fe1—C22A—C21A73.4 (10)
C3—C14—Fe1—C1931.1 (5)C20—Fe1—C22A—C21A29.9 (10)
C15—C14—Fe1—C22A179.2 (8)C23—Fe1—C22A—C21A114.3 (12)
C18—C14—Fe1—C22A62.0 (8)C20A—Fe1—C22A—C21A37.7 (9)
C3—C14—Fe1—C22A56.0 (8)C14—Fe1—C22A—C21A175.4 (8)
C15—C14—Fe1—C2060.3 (6)C23A—Fe1—C22A—C21A122.2 (16)
C18—C14—Fe1—C20179.1 (6)C16—Fe1—C22A—C21A57.6 (11)
C3—C14—Fe1—C2062.9 (7)C21—Fe1—C22A—C21A13.3 (12)
C15—C14—Fe1—C23132.9 (5)C18—Fe1—C22A—C21A143.5 (9)
C18—C14—Fe1—C23108.3 (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—C20A66.9 (10)C20A—Fe1—C22A—C23A84.4 (12)
C18—C14—Fe1—C15118.8 (2)C14—Fe1—C22A—C23A53.2 (16)
C3—C14—Fe1—C15123.2 (3)C16—Fe1—C22A—C23A179.8 (12)
C15—C14—Fe1—C23A142.8 (8)C21—Fe1—C22A—C23A135.5 (19)
C18—C14—Fe1—C23A98.4 (8)C18—Fe1—C22A—C23A94.3 (13)
C3—C14—Fe1—C23A19.6 (9)C17—Fe1—C22A—C23A138.9 (13)
C15—C14—Fe1—C1638.58 (18)C22A—C21A—C20A—C19A10 (3)
C18—C14—Fe1—C1680.26 (19)Fe1—C21A—C20A—C19A65 (2)
C3—C14—Fe1—C16161.8 (3)C22A—C21A—C20A—Fe154.9 (13)
C15—C14—Fe1—C21164.6 (14)C19—Fe1—C20A—C21A115.8 (17)
C18—C14—Fe1—C2145.7 (14)C22A—Fe1—C20A—C21A38.1 (9)
C3—C14—Fe1—C2172.3 (14)C20—Fe1—C20A—C21A17 (2)
C15—C14—Fe1—C18118.8 (2)C23—Fe1—C20A—C21A93.2 (13)
C3—C14—Fe1—C18118.0 (3)C15—Fe1—C20A—C21A136.4 (14)
C15—C14—Fe1—C1781.68 (18)C14—Fe1—C20A—C21A170.2 (12)
C18—C14—Fe1—C1737.16 (18)C23A—Fe1—C20A—C21A83.1 (11)
C3—C14—Fe1—C17155.1 (3)C16—Fe1—C20A—C21A93.8 (14)
C17—C16—Fe1—C19172.7 (7)C21—Fe1—C20A—C21A18.6 (11)
C15—C16—Fe1—C1967.5 (7)C17—Fe1—C20A—C21A64.2 (15)
C17—C16—Fe1—C22A71.0 (10)C19—Fe1—C20A—C19A0.4 (17)
C15—C16—Fe1—C22A169.1 (9)C22A—Fe1—C20A—C19A77.3 (13)
C17—C16—Fe1—C20132.4 (5)C20—Fe1—C20A—C19A99 (3)
C15—C16—Fe1—C20107.7 (5)C23—Fe1—C20A—C19A22.3 (14)
C17—C16—Fe1—C20A150.2 (8)C15—Fe1—C20A—C19A108.2 (14)
C15—C16—Fe1—C20A89.9 (8)C14—Fe1—C20A—C19A74.3 (16)
C17—C16—Fe1—C15119.9 (2)C23A—Fe1—C20A—C19A32.4 (12)
C17—C16—Fe1—C1481.80 (18)C16—Fe1—C20A—C19A150.8 (14)
C15—C16—Fe1—C1438.09 (16)C21—Fe1—C20A—C19A96.9 (14)
C17—C16—Fe1—C2187.8 (5)C17—Fe1—C20A—C19A179.7 (11)
C15—C16—Fe1—C21152.3 (5)C21A—C20A—C19A—C23A14 (3)
C17—C16—Fe1—C1837.58 (16)Fe1—C20A—C19A—C23A49 (2)
C15—C16—Fe1—C1882.31 (18)C21A—C20A—C19A—Fe163.4 (17)
C15—C16—Fe1—C17119.9 (2)C19—Fe1—C19A—C20A2 (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—C22A92.5 (9)C23—Fe1—C19A—C20A139 (2)
C14—C18—Fe1—C22A147.7 (9)C15—Fe1—C19A—C20A84.8 (15)
C17—C18—Fe1—C23150.7 (5)C14—Fe1—C19A—C20A128.7 (13)
C14—C18—Fe1—C2389.5 (5)C23A—Fe1—C19A—C20A129 (2)
C17—C18—Fe1—C1581.9 (2)C16—Fe1—C19A—C20A47 (2)
C14—C18—Fe1—C1537.91 (15)C21—Fe1—C19A—C20A63.3 (12)
C17—C18—Fe1—C14119.8 (3)C18—Fe1—C19A—C20A166.5 (10)
C17—C18—Fe1—C23A139.7 (8)C19—Fe1—C19A—C23A130 (9)
C14—C18—Fe1—C23A100.5 (8)C22A—Fe1—C19A—C23A42.6 (12)
C17—C18—Fe1—C1637.23 (18)C20—Fe1—C19A—C23A104.3 (17)
C14—C18—Fe1—C1682.55 (18)C23—Fe1—C19A—C23A10.2 (17)
C17—C18—Fe1—C2171.0 (5)C20A—Fe1—C19A—C23A129 (2)
C14—C18—Fe1—C21169.3 (4)C15—Fe1—C19A—C23A146.6 (14)
C14—C18—Fe1—C17119.8 (3)C14—Fe1—C19A—C23A102.6 (15)
C16—C17—Fe1—C22A133.0 (10)C16—Fe1—C19A—C23A175.5 (12)
C18—C17—Fe1—C22A107.6 (10)C21—Fe1—C19A—C23A65.3 (13)
C16—C17—Fe1—C2071.5 (6)C18—Fe1—C19A—C23A64.9 (19)
C18—C17—Fe1—C20169.1 (6)C21A—C22A—C23A—C19A5 (3)
C16—C17—Fe1—C23174.4 (8)Fe1—C22A—C23A—C19A65 (2)
C18—C17—Fe1—C2354.9 (8)C21A—C22A—C23A—Fe160.9 (15)
C16—C17—Fe1—C20A47.1 (10)C20A—C19A—C23A—C22A11 (4)
C18—C17—Fe1—C20A166.5 (10)Fe1—C19A—C23A—C22A60.5 (18)
C16—C17—Fe1—C1537.89 (17)C20A—C19A—C23A—Fe149 (2)
C18—C17—Fe1—C1581.52 (18)C19—Fe1—C23A—C22A104.7 (16)
C16—C17—Fe1—C1481.79 (18)C20—Fe1—C23A—C22A62.6 (11)
C18—C17—Fe1—C1437.62 (16)C23—Fe1—C23A—C22A144 (7)
C16—C17—Fe1—C23A175.5 (12)C20A—Fe1—C23A—C22A80.3 (11)
C18—C17—Fe1—C23A65.0 (12)C15—Fe1—C23A—C22A168.4 (11)
C18—C17—Fe1—C16119.4 (3)C14—Fe1—C23A—C22A152.1 (12)
C16—C17—Fe1—C21110.2 (5)C21—Fe1—C23A—C22A17.3 (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—C2355.9 (11)C19—Fe1—C23A—C19A7.9 (17)
C20—Fe1—C19—C23117.0 (11)C22A—Fe1—C23A—C19A112.6 (19)
C20A—Fe1—C19—C23144.8 (16)C20—Fe1—C23A—C19A50.0 (14)
C15—Fe1—C19—C23133.0 (8)C23—Fe1—C23A—C19A31 (6)
C14—Fe1—C19—C2388.8 (9)C20A—Fe1—C23A—C19A32.4 (12)
C23A—Fe1—C19—C2310.7 (14)C15—Fe1—C23A—C19A56 (2)
C16—Fe1—C19—C23173.5 (7)C14—Fe1—C23A—C19A95.2 (15)
C21—Fe1—C19—C2379.2 (8)C21—Fe1—C23A—C19A95.3 (15)
C18—Fe1—C19—C2351.2 (12)C18—Fe1—C23A—C19A140.1 (14)
C22A—Fe1—C19—C2061.1 (8)C17—Fe1—C23A—C19A179.9 (12)
C23—Fe1—C19—C20117.0 (11)
Hydrogen-bond geometry (Å, º) top
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.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C21H19N2O3)]
Mr468.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)9.6486 (7), 18.8900 (13), 11.8207 (9)
β (°) 93.248 (5)
V3)2151.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.73
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.864, 0.867
No. of measured, independent and
observed [I > 2σ(I)] reflections
20500, 5308, 3322
Rint0.042
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.123, 1.01
No. of reflections5308
No. of parameters344
No. of restraints5
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.25

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O30.972.472.877 (3)104.7
C9—H9···O10.932.583.128 (3)117.8
C10A—H10C···O1i0.982.563.371 (3)140.0
N5—H5A···O3ii0.861.992.840 (3)168.4
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y, z.
 

Acknowledgements

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

References

First citationBiot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678–4682.  Web of Science CrossRef CAS Google Scholar
First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613–625.  Web of Science CrossRef CAS Google Scholar
First citationGunasekaran, B., Kathiravan, S., Raghunathan, R. & Manivannan, V. (2009). Acta Cryst. E65, m1673.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationJaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505–2517.  Web of Science CrossRef PubMed CAS Google Scholar
First citationKamala, E. T. S., Nirmala, S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, m687–m688.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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