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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1528.
Published online 2010 November 6. doi:  10.1107/S1600536810043278
PMCID: PMC3011774

6-(4-Methyl­phen­yl)-2,10-dioxo-3,9-dioxa-6-aza-1(1,1′)-ferrocenacyclo­deca­phane

Abstract

In the title compound, [Fe(C23H23NO4)], the two cyclo­penta­dienyl (Cp) rings are nearly parallel, with a dihedral angle of 2.1 (1)°. The distance between the centroids of the Cp rings is 3.277 (8) Å. The relative orientation of the two Cp rings is characterized by a torsion angle of −64.3 (3)° defined by the two centroids and two substituted atoms.

Related literature

For the definition of ferrocenophanes, see: Otón et al. (2005 [triangle]). For the properties of ferrocenophanes, see: Cayuela et al. (2004 [triangle]); Kulbaba & Manners (2001 [triangle]); Lu et al. (2006 [triangle]); Mizuta et al. (2003 [triangle]); Nguyen et al. (1999 [triangle]); Otón et al. (2006a [triangle],b [triangle]); Suzaki et al. (2006 [triangle]). For a related structure, see: Gao et al. (2009 [triangle]). For the synthesis, see: Abd-Alla et al. (1993 [triangle]); Shivarkar et al. (2008 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1528-scheme1.jpg

Experimental

Crystal data

  • [Fe(C23H23NO4)]
  • M r = 433.27
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1528-efi1.jpg
  • a = 15.028 (2) Å
  • b = 11.7488 (17) Å
  • c = 22.765 (3) Å
  • V = 4019.3 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.78 mm−1
  • T = 296 K
  • 0.33 × 0.25 × 0.15 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.784, T max = 0.894
  • 19079 measured reflections
  • 3568 independent reflections
  • 2357 reflections with I > 2σ(I)
  • R int = 0.057

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.128
  • S = 1.00
  • 3568 reflections
  • 263 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043278/hy2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043278/hy2361Isup2.hkl

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

Acknowledgments

Financial support from the National Natural Science Foundation of China (grant No. 20972125) is gratefully acknowledged.

supplementary crystallographic information

Comment

Ferrocenophanes, in which the two cyclopentadienyl (Cp) rings are joined by an atomic or molecular bridge (Otón et al., 2005), are found to be aromatic, highly stable and generally non-toxic, and have reversible redox characteristics (Mizuta et al., 2003). In particular, ferrocenophanes are useful precursors to poly-ferrocenyl materials (Kulbaba & Manners, 2001; Nguyen et al., 1999) and act as potential receptor towards cation or anion recognition (Cayuela et al., 2004; Lu et al., 2006; Suzaki et al., 2006; Otón et al., 2006a,b). As a part of our ongoing investigation of ferrocenophanes, the title compound has been prepared and we report here its crystal structure. Despite of the fact that structually characterized ferrocenophanes are well presented in the Cambridge Structural Database (Allen, 2002; Version 5.27, release February 2009), there is only one analogous compound structurally characterized (Gao et al., 2009). From this viewpoint, X-ray single-crystal study of the title compound presents a certain descriptive interest.

The structure of the title compound is show in Fig. 1. The two Cp rings are nearly parallel, making a dihedral angle of 2.1 (1)°. The distance between the centroids of the Cp rings is 3.277 (8) Å. The angle formed between the two centroids and Fe1 is 177.67 (16)°. The relative orientation of the two Cp rings is characterized by the C10—Cg1—Cg2—C13 torsion angle of -64.3 (3)° (Cg1 and Cg2 are the centroids of C14–C18 ring and C19–C23 ring, respectively). The Fe—C distances range from 2.005 (3) to 2.045 (4) Å. The exocyclic bond lengths C13—C19 and C10—C14 are 1.453 (4) and 1.467 (5) Å, respectively.

Experimental

2,2'-(p-Tolylazanediyl)diethanol was prepared as described by Shivarkar et al. (2008). 1,1'-Ferrocenedi(carbonyl chloride) was prepared as described by Abd-Alla et al. (1993). For the preparation of ferrocenophane, a mixture of 1,1'-ferrocenedi(carbonyl chloride) (2 g, 0.006 mol), dry dichloromethane (500 ml) and pyridine (1 ml, 0.012 mol) was stirred in dark. To this solution 2,2'-(p-tolylazanediyl)diethanol (0.006 mol) in dichloromethane was added dropwise over 1 h. The mixture was stirred for 24 h and then refluxed for another 8 h (monitored by TLC). The solvent was removed under atmospheric pressure. The residue was then purified by column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1:2) (yield: 38%). Melting point and NMR spectra confirmed identity and purity of the prepared compound.

Dark-red crystals of the title compound were obtained by slow concentration of a dichloromethane solution at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2(1.5 for methyl)Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

[Fe(C23H23NO4)]Dx = 1.432 Mg m3
Mr = 433.27Melting point: 407(8) K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2477 reflections
a = 15.028 (2) Åθ = 2.4–19.6°
b = 11.7488 (17) ŵ = 0.78 mm1
c = 22.765 (3) ÅT = 296 K
V = 4019.3 (10) Å3Block, dark-red
Z = 80.33 × 0.25 × 0.15 mm
F(000) = 1808

Data collection

Bruker APEXII CCD diffractometer3568 independent reflections
Radiation source: fine-focus sealed tube2357 reflections with I > 2σ(I)
graphiteRint = 0.057
[var phi] and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −17→17
Tmin = 0.784, Tmax = 0.894k = −14→12
19079 measured reflectionsl = −27→24

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0623P)2 + 1.0856P] where P = (Fo2 + 2Fc2)/3
3568 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.43 e Å3

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

xyzUiso*/Ueq
Fe10.12595 (3)1.22967 (4)0.052251 (19)0.05457 (19)
N10.00836 (17)0.8972 (2)0.20855 (11)0.0599 (7)
O10.16563 (14)0.9967 (2)0.15793 (9)0.0653 (6)
O20.26745 (17)1.1325 (3)0.17458 (12)0.1046 (10)
O3−0.03453 (13)1.13781 (17)0.17171 (9)0.0586 (6)
O4−0.11312 (18)1.1282 (3)0.08862 (13)0.1183 (12)
C1−0.1716 (3)0.5112 (3)0.10871 (16)0.0796 (11)
H1A−0.20310.47260.13950.119*
H1B−0.12850.46040.09180.119*
H1C−0.21280.53490.07900.119*
C2−0.1247 (2)0.6140 (3)0.13363 (14)0.0589 (8)
C3−0.0345 (2)0.6298 (3)0.12735 (14)0.0673 (9)
H3−0.00170.57610.10650.081*
C40.0090 (2)0.7224 (3)0.15085 (14)0.0629 (9)
H40.06980.73080.14450.075*
C5−0.0357 (2)0.8035 (3)0.18383 (13)0.0506 (7)
C6−0.1279 (2)0.7883 (3)0.18891 (14)0.0598 (9)
H6−0.16130.84160.20960.072*
C7−0.1698 (2)0.6964 (3)0.16399 (14)0.0616 (9)
H7−0.23120.68980.16790.074*
C80.0986 (2)0.8793 (3)0.23124 (16)0.0692 (10)
H8A0.12370.81200.21290.083*
H8B0.09550.86540.27320.083*
C90.1598 (2)0.9792 (3)0.22014 (15)0.0716 (10)
H9A0.13641.04690.23900.086*
H9B0.21830.96380.23620.086*
C100.2191 (2)1.0829 (4)0.14117 (17)0.0723 (10)
C11−0.0434 (2)0.9829 (3)0.23940 (14)0.0659 (9)
H11A−0.00351.02870.26310.079*
H11B−0.08440.94490.26580.079*
C12−0.0951 (2)1.0596 (3)0.20000 (15)0.0644 (9)
H12A−0.12621.01500.17060.077*
H12B−0.13881.10150.22270.077*
C13−0.0522 (2)1.1668 (3)0.11655 (15)0.0624 (9)
C140.2097 (2)1.1067 (3)0.07820 (16)0.0707 (10)
C150.1458 (3)1.0613 (3)0.03878 (16)0.0754 (11)
H150.10350.99980.04700.091*
C160.1557 (4)1.1210 (4)−0.01512 (17)0.0932 (14)
H160.11971.1093−0.05050.112*
C170.2232 (3)1.2012 (4)−0.0088 (2)0.0953 (14)
H170.24251.2553−0.03900.114*
C180.2579 (3)1.1935 (4)0.04834 (19)0.0934 (14)
H180.30631.23960.06470.112*
C190.0083 (2)1.2533 (3)0.09438 (14)0.0550 (8)
C200.0773 (3)1.3066 (3)0.12548 (15)0.0713 (10)
H200.09501.29090.16610.086*
C210.1165 (3)1.3873 (3)0.0874 (2)0.0986 (14)
H210.16681.43680.09720.118*
C220.0727 (3)1.3847 (4)0.0337 (2)0.0963 (14)
H220.08661.4318−0.00060.116*
C230.0055 (3)1.3034 (4)0.03710 (17)0.0786 (11)
H23−0.03601.28320.00560.094*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0526 (3)0.0578 (3)0.0533 (3)0.0040 (2)0.0076 (2)−0.0010 (2)
N10.0557 (16)0.0556 (17)0.0683 (17)0.0009 (13)−0.0075 (13)0.0035 (14)
O10.0595 (13)0.0737 (17)0.0626 (15)0.0009 (12)−0.0063 (11)0.0061 (12)
O20.0675 (17)0.139 (3)0.107 (2)−0.0402 (17)−0.0299 (16)0.040 (2)
O30.0619 (13)0.0543 (14)0.0596 (13)−0.0074 (10)0.0036 (10)0.0053 (11)
O40.084 (2)0.181 (4)0.090 (2)−0.056 (2)−0.0187 (16)0.031 (2)
C10.086 (3)0.076 (3)0.077 (3)−0.006 (2)−0.001 (2)−0.006 (2)
C20.060 (2)0.060 (2)0.0558 (19)0.0012 (17)−0.0036 (15)−0.0005 (16)
C30.061 (2)0.074 (3)0.066 (2)0.0120 (18)0.0029 (16)−0.0155 (18)
C40.0422 (17)0.079 (2)0.068 (2)0.0032 (17)0.0019 (15)−0.0058 (19)
C50.0497 (17)0.0499 (19)0.0522 (17)0.0038 (15)0.0003 (14)0.0093 (15)
C60.0491 (18)0.057 (2)0.073 (2)0.0069 (16)0.0139 (16)0.0020 (17)
C70.0476 (18)0.063 (2)0.074 (2)−0.0057 (16)0.0036 (16)0.0035 (18)
C80.066 (2)0.066 (2)0.076 (2)−0.0091 (18)−0.0226 (18)0.0185 (19)
C90.068 (2)0.080 (3)0.067 (2)−0.0086 (19)−0.0201 (18)0.0114 (19)
C100.0417 (18)0.095 (3)0.081 (3)0.006 (2)0.0005 (18)0.018 (2)
C110.076 (2)0.063 (2)0.059 (2)−0.0052 (18)0.0068 (17)0.0044 (17)
C120.0600 (19)0.054 (2)0.079 (2)0.0017 (17)0.0174 (17)0.0076 (18)
C130.0496 (19)0.074 (2)0.064 (2)0.0004 (17)0.0087 (17)−0.0032 (18)
C140.053 (2)0.086 (3)0.073 (2)0.0204 (18)0.0110 (18)0.011 (2)
C150.097 (3)0.062 (2)0.067 (2)0.024 (2)0.006 (2)−0.0123 (19)
C160.128 (4)0.096 (3)0.056 (2)0.047 (3)0.011 (2)−0.013 (2)
C170.085 (3)0.117 (4)0.084 (3)0.034 (3)0.035 (2)0.020 (3)
C180.053 (2)0.128 (4)0.100 (3)0.010 (2)0.017 (2)0.041 (3)
C190.0543 (18)0.054 (2)0.0570 (19)0.0107 (15)0.0090 (15)0.0019 (15)
C200.094 (3)0.057 (2)0.063 (2)−0.011 (2)0.020 (2)−0.0145 (17)
C210.123 (4)0.060 (3)0.113 (4)−0.029 (2)0.040 (3)−0.019 (3)
C220.128 (4)0.061 (3)0.100 (3)0.018 (3)0.046 (3)0.014 (2)
C230.071 (2)0.089 (3)0.075 (2)0.031 (2)0.0124 (19)0.022 (2)

Geometric parameters (Å, °)

Fe1—C142.005 (3)C7—H70.9300
Fe1—C212.022 (4)C8—C91.512 (4)
Fe1—C152.024 (4)C8—H8A0.9700
Fe1—C182.030 (4)C8—H8B0.9700
Fe1—C192.031 (3)C9—H9A0.9700
Fe1—C202.033 (3)C9—H9B0.9700
Fe1—C222.034 (4)C10—C141.467 (5)
Fe1—C232.036 (4)C11—C121.489 (4)
Fe1—C172.045 (4)C11—H11A0.9700
Fe1—C162.045 (4)C11—H11B0.9700
N1—C51.402 (4)C12—H12A0.9700
N1—C111.453 (4)C12—H12B0.9700
N1—C81.467 (4)C13—C191.453 (4)
O1—C101.348 (4)C14—C151.418 (5)
O1—C91.434 (4)C14—C181.424 (5)
O2—C101.203 (4)C15—C161.421 (5)
O3—C131.328 (4)C15—H150.9800
O3—C121.445 (4)C16—C171.392 (6)
O4—C131.204 (4)C16—H160.9800
C1—C21.509 (5)C17—C181.405 (6)
C1—H1A0.9600C17—H170.9800
C1—H1B0.9600C18—H180.9800
C1—H1C0.9600C19—C201.404 (5)
C2—C71.368 (5)C19—C231.432 (5)
C2—C31.377 (4)C20—C211.413 (5)
C3—C41.377 (4)C20—H200.9800
C3—H30.9300C21—C221.389 (6)
C4—C51.387 (4)C21—H210.9800
C4—H40.9300C22—C231.392 (6)
C5—C61.401 (4)C22—H220.9800
C6—C71.374 (4)C23—H230.9800
C6—H60.9300
C14—Fe1—C21126.0 (2)C8—C9—H9A110.0
C14—Fe1—C1541.22 (15)O1—C9—H9B110.0
C21—Fe1—C15164.88 (19)C8—C9—H9B110.0
C14—Fe1—C1841.32 (15)H9A—C9—H9B108.4
C21—Fe1—C18106.1 (2)O2—C10—O1123.1 (3)
C15—Fe1—C1869.19 (19)O2—C10—C14125.7 (4)
C14—Fe1—C19120.38 (14)O1—C10—C14111.3 (3)
C21—Fe1—C1968.10 (15)N1—C11—C12114.0 (3)
C15—Fe1—C19109.48 (15)N1—C11—H11A108.7
C18—Fe1—C19154.15 (15)C12—C11—H11A108.7
C14—Fe1—C20107.74 (16)N1—C11—H11B108.7
C21—Fe1—C2040.79 (15)C12—C11—H11B108.7
C15—Fe1—C20127.75 (15)H11A—C11—H11B107.6
C18—Fe1—C20118.71 (18)O3—C12—C11109.0 (3)
C19—Fe1—C2040.42 (13)O3—C12—H12A109.9
C14—Fe1—C22162.5 (2)C11—C12—H12A109.9
C21—Fe1—C2240.05 (18)O3—C12—H12B109.9
C15—Fe1—C22154.39 (19)C11—C12—H12B109.9
C18—Fe1—C22124.2 (2)H12A—C12—H12B108.3
C19—Fe1—C2268.48 (15)O4—C13—O3123.7 (3)
C20—Fe1—C2268.32 (17)O4—C13—C19123.8 (3)
C14—Fe1—C23156.13 (16)O3—C13—C19112.5 (3)
C21—Fe1—C2367.3 (2)C15—C14—C18108.2 (4)
C15—Fe1—C23121.41 (18)C15—C14—C10127.7 (4)
C18—Fe1—C23161.81 (16)C18—C14—C10123.6 (4)
C19—Fe1—C2341.21 (13)C15—C14—Fe170.1 (2)
C20—Fe1—C2368.28 (16)C18—C14—Fe170.3 (2)
C22—Fe1—C2340.00 (17)C10—C14—Fe1119.1 (2)
C14—Fe1—C1768.53 (16)C14—C15—C16106.8 (4)
C21—Fe1—C17118.0 (2)C14—C15—Fe168.7 (2)
C15—Fe1—C1768.40 (18)C16—C15—Fe170.4 (2)
C18—Fe1—C1740.33 (16)C14—C15—H15126.6
C19—Fe1—C17165.00 (18)C16—C15—H15126.6
C20—Fe1—C17152.5 (2)Fe1—C15—H15126.6
C22—Fe1—C17106.63 (18)C17—C16—C15108.8 (4)
C23—Fe1—C17126.15 (17)C17—C16—Fe170.1 (2)
C14—Fe1—C1668.52 (16)C15—C16—Fe168.8 (2)
C21—Fe1—C16152.1 (2)C17—C16—H16125.6
C15—Fe1—C1640.88 (16)C15—C16—H16125.6
C18—Fe1—C1667.8 (2)Fe1—C16—H16125.6
C19—Fe1—C16129.04 (19)C16—C17—C18108.8 (4)
C20—Fe1—C16166.29 (19)C16—C17—Fe170.1 (2)
C22—Fe1—C16119.29 (18)C18—C17—Fe169.3 (2)
C23—Fe1—C16109.46 (18)C16—C17—H17125.6
C17—Fe1—C1639.81 (17)C18—C17—H17125.6
C5—N1—C11119.0 (3)Fe1—C17—H17125.6
C5—N1—C8117.8 (3)C17—C18—C14107.4 (4)
C11—N1—C8115.1 (3)C17—C18—Fe170.4 (2)
C10—O1—C9115.1 (3)C14—C18—Fe168.4 (2)
C13—O3—C12117.3 (3)C17—C18—H18126.3
C2—C1—H1A109.5C14—C18—H18126.3
C2—C1—H1B109.5Fe1—C18—H18126.3
H1A—C1—H1B109.5C20—C19—C23107.3 (3)
C2—C1—H1C109.5C20—C19—C13126.8 (3)
H1A—C1—H1C109.5C23—C19—C13125.9 (3)
H1B—C1—H1C109.5C20—C19—Fe169.85 (18)
C7—C2—C3116.4 (3)C23—C19—Fe169.60 (18)
C7—C2—C1121.7 (3)C13—C19—Fe1127.8 (2)
C3—C2—C1121.9 (3)C19—C20—C21107.3 (4)
C2—C3—C4122.2 (3)C19—C20—Fe169.73 (18)
C2—C3—H3118.9C21—C20—Fe169.2 (2)
C4—C3—H3118.9C19—C20—H20126.3
C3—C4—C5121.6 (3)C21—C20—H20126.3
C3—C4—H4119.2Fe1—C20—H20126.3
C5—C4—H4119.2C22—C21—C20109.1 (4)
C4—C5—C6115.8 (3)C22—C21—Fe170.4 (2)
C4—C5—N1121.8 (3)C20—C21—Fe170.0 (2)
C6—C5—N1122.3 (3)C22—C21—H21125.4
C7—C6—C5121.3 (3)C20—C21—H21125.4
C7—C6—H6119.3Fe1—C21—H21125.4
C5—C6—H6119.3C21—C22—C23108.0 (4)
C2—C7—C6122.5 (3)C21—C22—Fe169.5 (2)
C2—C7—H7118.7C23—C22—Fe170.1 (2)
C6—C7—H7118.7C21—C22—H22126.0
N1—C8—C9113.1 (3)C23—C22—H22126.0
N1—C8—H8A109.0Fe1—C22—H22126.0
C9—C8—H8A109.0C22—C23—C19108.2 (4)
N1—C8—H8B109.0C22—C23—Fe169.9 (2)
C9—C8—H8B109.0C19—C23—Fe169.19 (18)
H8A—C8—H8B107.8C22—C23—H23125.9
O1—C9—C8108.3 (3)C19—C23—H23125.9
O1—C9—H9A110.0Fe1—C23—H23125.9
C7—C2—C3—C40.8 (5)C19—Fe1—C18—C17172.7 (3)
C1—C2—C3—C4−178.8 (3)C20—Fe1—C18—C17−156.7 (3)
C2—C3—C4—C52.0 (5)C22—Fe1—C18—C17−74.5 (4)
C3—C4—C5—C6−3.3 (5)C23—Fe1—C18—C17−48.3 (8)
C3—C4—C5—N1179.1 (3)C16—Fe1—C18—C1736.7 (3)
C11—N1—C5—C4176.1 (3)C21—Fe1—C18—C14126.7 (3)
C8—N1—C5—C4−36.8 (4)C15—Fe1—C18—C14−38.1 (2)
C11—N1—C5—C6−1.4 (4)C19—Fe1—C18—C1453.8 (5)
C8—N1—C5—C6145.7 (3)C20—Fe1—C18—C1484.4 (3)
C4—C5—C6—C71.9 (5)C22—Fe1—C18—C14166.6 (3)
N1—C5—C6—C7179.5 (3)C23—Fe1—C18—C14−167.2 (5)
C3—C2—C7—C6−2.2 (5)C17—Fe1—C18—C14−118.9 (4)
C1—C2—C7—C6177.4 (3)C16—Fe1—C18—C14−82.2 (3)
C5—C6—C7—C20.8 (5)O4—C13—C19—C20176.1 (4)
C5—N1—C8—C9142.6 (3)O3—C13—C19—C20−1.8 (5)
C11—N1—C8—C9−69.0 (4)O4—C13—C19—C23−0.9 (6)
C10—O1—C9—C8−179.3 (3)O3—C13—C19—C23−178.8 (3)
N1—C8—C9—O1−60.2 (4)O4—C13—C19—Fe1−91.8 (4)
C9—O1—C10—O29.3 (5)O3—C13—C19—Fe190.2 (3)
C9—O1—C10—C14−170.6 (3)C14—Fe1—C19—C2081.7 (3)
C5—N1—C11—C12−74.8 (4)C21—Fe1—C19—C20−38.2 (2)
C8—N1—C11—C12137.3 (3)C15—Fe1—C19—C20125.9 (2)
C13—O3—C12—C11144.0 (3)C18—Fe1—C19—C2043.6 (5)
N1—C11—C12—O3−73.6 (4)C22—Fe1—C19—C20−81.4 (3)
C12—O3—C13—O4−3.1 (5)C23—Fe1—C19—C20−118.3 (3)
C12—O3—C13—C19174.9 (2)C17—Fe1—C19—C20−155.0 (6)
O2—C10—C14—C15−171.0 (4)C16—Fe1—C19—C20167.7 (2)
O1—C10—C14—C158.8 (5)C14—Fe1—C19—C23−160.0 (3)
O2—C10—C14—C180.0 (6)C21—Fe1—C19—C2380.2 (3)
O1—C10—C14—C18179.9 (3)C15—Fe1—C19—C23−115.8 (3)
O2—C10—C14—Fe1−84.6 (4)C18—Fe1—C19—C23161.9 (4)
O1—C10—C14—Fe195.3 (4)C20—Fe1—C19—C23118.3 (3)
C21—Fe1—C14—C15169.0 (2)C22—Fe1—C19—C2336.9 (3)
C18—Fe1—C14—C15−118.8 (3)C17—Fe1—C19—C23−36.7 (7)
C19—Fe1—C14—C1585.3 (3)C16—Fe1—C19—C23−74.0 (3)
C20—Fe1—C14—C15127.6 (2)C14—Fe1—C19—C13−39.8 (4)
C22—Fe1—C14—C15−158.3 (5)C21—Fe1—C19—C13−159.7 (4)
C23—Fe1—C14—C1551.3 (5)C15—Fe1—C19—C134.4 (3)
C17—Fe1—C14—C15−81.3 (3)C18—Fe1—C19—C13−77.9 (5)
C16—Fe1—C14—C15−38.4 (3)C20—Fe1—C19—C13−121.5 (4)
C21—Fe1—C14—C18−72.2 (3)C22—Fe1—C19—C13157.1 (4)
C15—Fe1—C14—C18118.8 (3)C23—Fe1—C19—C13120.2 (4)
C19—Fe1—C14—C18−155.9 (3)C17—Fe1—C19—C1383.5 (7)
C20—Fe1—C14—C18−113.6 (3)C16—Fe1—C19—C1346.1 (4)
C22—Fe1—C14—C18−39.5 (6)C23—C19—C20—C21−0.6 (4)
C23—Fe1—C14—C18170.1 (4)C13—C19—C20—C21−178.0 (3)
C17—Fe1—C14—C1837.5 (3)Fe1—C19—C20—C2159.2 (3)
C16—Fe1—C14—C1880.4 (3)C23—C19—C20—Fe1−59.8 (2)
C21—Fe1—C14—C1046.1 (4)C13—C19—C20—Fe1122.7 (3)
C15—Fe1—C14—C10−122.9 (4)C14—Fe1—C20—C19−116.3 (2)
C18—Fe1—C14—C10118.3 (5)C21—Fe1—C20—C19118.7 (4)
C19—Fe1—C14—C10−37.6 (4)C15—Fe1—C20—C19−75.0 (3)
C20—Fe1—C14—C104.7 (4)C18—Fe1—C20—C19−160.0 (2)
C22—Fe1—C14—C1078.8 (6)C22—Fe1—C20—C1981.8 (3)
C23—Fe1—C14—C10−71.5 (6)C23—Fe1—C20—C1938.6 (2)
C17—Fe1—C14—C10155.8 (4)C17—Fe1—C20—C19166.3 (3)
C16—Fe1—C14—C10−161.3 (4)C16—Fe1—C20—C19−44.5 (8)
C18—C14—C15—C160.1 (4)C14—Fe1—C20—C21125.0 (3)
C10—C14—C15—C16172.2 (3)C15—Fe1—C20—C21166.3 (3)
Fe1—C14—C15—C1660.3 (2)C18—Fe1—C20—C2181.4 (3)
C18—C14—C15—Fe1−60.3 (3)C19—Fe1—C20—C21−118.7 (4)
C10—C14—C15—Fe1111.9 (4)C22—Fe1—C20—C21−36.8 (3)
C21—Fe1—C15—C14−36.2 (7)C23—Fe1—C20—C21−80.0 (3)
C18—Fe1—C15—C1438.2 (2)C17—Fe1—C20—C2147.6 (5)
C19—Fe1—C15—C14−114.2 (2)C16—Fe1—C20—C21−163.1 (7)
C20—Fe1—C15—C14−72.6 (3)C19—C20—C21—C220.2 (5)
C22—Fe1—C15—C14165.1 (3)Fe1—C20—C21—C2259.7 (3)
C23—Fe1—C15—C14−158.3 (2)C19—C20—C21—Fe1−59.6 (2)
C17—Fe1—C15—C1481.6 (3)C14—Fe1—C21—C22165.4 (2)
C16—Fe1—C15—C14118.0 (4)C15—Fe1—C21—C22−165.8 (6)
C14—Fe1—C15—C16−118.0 (4)C18—Fe1—C21—C22124.5 (3)
C21—Fe1—C15—C16−154.3 (6)C19—Fe1—C21—C22−82.2 (3)
C18—Fe1—C15—C16−79.8 (3)C20—Fe1—C21—C22−120.0 (4)
C19—Fe1—C15—C16127.8 (3)C23—Fe1—C21—C22−37.5 (2)
C20—Fe1—C15—C16169.4 (3)C17—Fe1—C21—C2282.7 (3)
C22—Fe1—C15—C1647.1 (5)C16—Fe1—C21—C2251.6 (5)
C23—Fe1—C15—C1683.7 (3)C14—Fe1—C21—C20−74.6 (3)
C17—Fe1—C15—C16−36.4 (3)C15—Fe1—C21—C20−45.8 (8)
C14—C15—C16—C17−0.4 (4)C18—Fe1—C21—C20−115.5 (3)
Fe1—C15—C16—C1758.8 (3)C19—Fe1—C21—C2037.8 (2)
C14—C15—C16—Fe1−59.2 (2)C22—Fe1—C21—C20120.0 (4)
C14—Fe1—C16—C17−81.8 (3)C23—Fe1—C21—C2082.5 (3)
C21—Fe1—C16—C1745.5 (5)C17—Fe1—C21—C20−157.3 (3)
C15—Fe1—C16—C17−120.5 (4)C16—Fe1—C21—C20171.6 (4)
C18—Fe1—C16—C17−37.2 (3)C20—C21—C22—C230.3 (5)
C19—Fe1—C16—C17165.8 (2)Fe1—C21—C22—C2359.8 (3)
C20—Fe1—C16—C17−158.4 (7)C20—C21—C22—Fe1−59.5 (3)
C22—Fe1—C16—C1780.8 (3)C14—Fe1—C22—C21−42.7 (6)
C23—Fe1—C16—C17123.6 (3)C15—Fe1—C22—C21171.5 (3)
C14—Fe1—C16—C1538.7 (2)C18—Fe1—C22—C21−73.3 (3)
C21—Fe1—C16—C15166.0 (4)C19—Fe1—C22—C2181.1 (3)
C18—Fe1—C16—C1583.4 (3)C20—Fe1—C22—C2137.5 (2)
C19—Fe1—C16—C15−73.7 (3)C23—Fe1—C22—C21119.1 (4)
C20—Fe1—C16—C15−37.9 (9)C17—Fe1—C22—C21−113.9 (3)
C22—Fe1—C16—C15−158.7 (3)C16—Fe1—C22—C21−155.1 (3)
C23—Fe1—C16—C15−115.9 (3)C14—Fe1—C22—C23−161.8 (4)
C17—Fe1—C16—C15120.5 (4)C21—Fe1—C22—C23−119.1 (4)
C15—C16—C17—C180.6 (5)C15—Fe1—C22—C2352.4 (5)
Fe1—C16—C17—C1858.6 (3)C18—Fe1—C22—C23167.6 (3)
C15—C16—C17—Fe1−58.0 (3)C19—Fe1—C22—C23−38.0 (2)
C14—Fe1—C17—C1681.8 (3)C20—Fe1—C22—C23−81.6 (3)
C21—Fe1—C17—C16−157.8 (3)C17—Fe1—C22—C23127.0 (3)
C15—Fe1—C17—C1637.3 (3)C16—Fe1—C22—C2385.7 (3)
C18—Fe1—C17—C16120.2 (4)C21—C22—C23—C19−0.6 (4)
C19—Fe1—C17—C16−47.4 (8)Fe1—C22—C23—C1958.8 (2)
C20—Fe1—C17—C16169.1 (3)C21—C22—C23—Fe1−59.4 (3)
C22—Fe1—C17—C16−116.0 (3)C20—C19—C23—C220.7 (4)
C23—Fe1—C17—C16−76.6 (3)C13—C19—C23—C22178.3 (3)
C14—Fe1—C17—C18−38.4 (3)Fe1—C19—C23—C22−59.2 (3)
C21—Fe1—C17—C1882.0 (4)C20—C19—C23—Fe160.0 (2)
C15—Fe1—C17—C18−82.9 (3)C13—C19—C23—Fe1−122.5 (3)
C19—Fe1—C17—C18−167.6 (6)C14—Fe1—C23—C22166.6 (4)
C20—Fe1—C17—C1848.9 (5)C21—Fe1—C23—C2237.5 (2)
C22—Fe1—C17—C18123.8 (3)C15—Fe1—C23—C22−156.3 (3)
C23—Fe1—C17—C18163.2 (3)C18—Fe1—C23—C22−34.6 (7)
C16—Fe1—C17—C18−120.2 (4)C19—Fe1—C23—C22119.6 (4)
C16—C17—C18—C14−0.6 (5)C20—Fe1—C23—C2281.7 (3)
Fe1—C17—C18—C1458.6 (3)C17—Fe1—C23—C22−71.4 (3)
C16—C17—C18—Fe1−59.2 (3)C16—Fe1—C23—C22−112.7 (3)
C15—C14—C18—C170.3 (4)C14—Fe1—C23—C1946.9 (5)
C10—C14—C18—C17−172.2 (3)C21—Fe1—C23—C19−82.1 (2)
Fe1—C14—C18—C17−59.8 (3)C15—Fe1—C23—C1984.0 (3)
C15—C14—C18—Fe160.2 (2)C18—Fe1—C23—C19−154.3 (6)
C10—C14—C18—Fe1−112.4 (3)C20—Fe1—C23—C19−37.9 (2)
C14—Fe1—C18—C17118.9 (4)C22—Fe1—C23—C19−119.6 (4)
C21—Fe1—C18—C17−114.4 (3)C17—Fe1—C23—C19169.0 (3)
C15—Fe1—C18—C1780.8 (3)C16—Fe1—C23—C19127.6 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2361).

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