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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): m687–m688.
Published online 2009 May 29. doi:  10.1107/S1600536809018583
PMCID: PMC2969822

Methyl 5-ferrocenyl-5a-hydr­oxy-1-methyl-10-oxo-2,3,3a,4,5a,10-hexa­hydro-1H-indeno[1,2:2′,3′]furo[3′,4′-b]pyrrole-3a-carboxyl­ate

Abstract

In the title compound, [Fe(C5H5)(C21H20NO5)], the pyrrolidine and cyclo­penta­none rings exhibit a twist conformation. The pyrrolidine ring is almost perpendicular to the cyclo­penta­none ring, making a dihedral angle of 81.91 (6)°. The mol­ecular conformation is stabilized by an intra­molecular O—H(...)N hydrogen bond and C—H(...)O inter­actions. The crystal structure is stabilized by inter­molecular C—H(...)O inter­actions.

Related literature

For general background and uses of ferrocene-based ligands, see Gomez Arrayas et al. (2006 [triangle]); Blaser & Schmidt (2004 [triangle]); Johnson & Sames (2000 [triangle]); Baar et al. (2000 [triangle]); Staveren & Metzler-Nolte (2004 [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]). For asymmetry parameters, see: Nardelli (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m687-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C21H20NO5)]
  • M r = 487.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m687-efi1.jpg
  • a = 7.7292 (2) Å
  • b = 24.7713 (7) Å
  • c = 11.8120 (4) Å
  • β = 93.4450 (10)°
  • V = 2257.47 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.71 mm−1
  • T = 293 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.816, T max = 0.872
  • 32884 measured reflections
  • 7917 independent reflections
  • 6016 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.123
  • S = 1.05
  • 7917 reflections
  • 299 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2004 [triangle]); data reduction: APEX2 and SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018583/bt2949sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018583/bt2949Isup2.hkl

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

Acknowledgments

ETSK thanks Professors M. N. Ponnusamy and D. Velmurugan, Department of Crystallography and Biophysics, University of Madras, India, for their guidance and valuable suggestions. ETSK also thanks Dr Babu Varghese, SAIF, IIT-Madras, and the SRM management for their support.

supplementary crystallographic information

Comment

Ferrocene-based ligands incorporating chirality are very important (Gomez Arrayas et al., 2006) and some of them have already been applied in industrial processes because of their stability, low price and unique structure (Blaser & Schmidt, 2004). Transition metal complexes derived from ferrocene have attracted great intrest due to their applications as precursors for the synthesis of organic as well as organometallic compounds (Johnson & Sames, 2000), in homogeneous catalysis (Baar et al., 2000), or even in biological chemistry (Staveren & Metzler-Nolte, 2004).

Fig. 1 shows the ORTEP plot of compound (I). Bond lengths and angles are comparable with other reported values.

In the molecule the pyrrolidine ring N1/C1/C2/C3/C4 exhibits twist conformation with assymetry parameters (Nardelli, 1983) ΔCs(C1) = 12.47 (2)/ (C2) = 17.76 (21) and with the puckering parameters (Cremer & Pople, 1975) q2 = 0.3819 (2) Å and [var phi]2 = 53.2 (2)°. The cyclopentanone ring also exhibits twist conformation with assymetry parameters ΔCs(C4) = 4.07 (2)/ (C12) = 4.11 (2) and with the puckering parameters q2 = 0.1106 (2) Å and [var phi]2 = 343.6 (8)°. The sum of bond angles around N1 [341.70 (4)°] indicates sp2 hybridization. The pyrrolidine ring is almost perpendicular to the cyclopentanone ring making a dihedral angle of 81.91 (6)° and the ferrocene ring is perpendicular to the phenyl ring with a dihedral angle of 84.37 (8)°. The cyclopentanone and the phenyl rings are planar with each other making an angle of 5.06 (5)°.

In the crystal packing, atoms O3 and O4 are involved in intermolecular C—H···O interactions and atom O2 contributes to N—H···O intramolecular interactions.

Experimental

A mixture of ferrocenyl Baylis–Hillman adduct, sarcosine and ninhydrin were refluxed in 1,2-dichloethane for 35 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. The product was recrystallized from dry benzene by slow evaporation.

Refinement

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.93 or 0.96 Å and Uiso(H)= 1.2–1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) with 30% probability displacement ellipsoids.
Fig. 2.
The packing of the molecules viewed along b axis.

Crystal data

[Fe(C5H5)(C21H20NO5)]F(000) = 1016
Mr = 487.32Dx = 1.434 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 32884 reflections
a = 7.7292 (2) Åθ = 1.6–32.1°
b = 24.7713 (7) ŵ = 0.71 mm1
c = 11.8120 (4) ÅT = 293 K
β = 93.445 (1)°Prism, orange
V = 2257.47 (12) Å30.30 × 0.25 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer7917 independent reflections
Radiation source: fine-focus sealed tube6016 reflections with I > 2σ(I)
graphiteRint = 0.028
ω and [var phi] scansθmax = 32.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→10
Tmin = 0.816, Tmax = 0.872k = −37→34
32884 measured reflectionsl = −17→17

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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.067P)2 + 0.4193P] where P = (Fo2 + 2Fc2)/3
7917 reflections(Δ/σ)max < 0.001
299 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.35 e Å3

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 > σ(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
C10.4102 (2)0.20020 (8)0.59190 (15)0.0407 (4)
H1A0.40530.23760.56780.049*
H1B0.52540.19240.62490.049*
C20.2738 (2)0.18825 (7)0.67450 (13)0.0346 (3)
H2A0.26340.21780.72760.042*
H2B0.30080.15540.71650.042*
C30.10722 (17)0.18175 (5)0.59839 (11)0.0248 (2)
C40.17555 (18)0.15859 (5)0.48640 (11)0.0270 (3)
C50.0840 (2)0.18021 (6)0.37684 (11)0.0305 (3)
C6−0.0361 (2)0.13816 (6)0.33231 (11)0.0306 (3)
C7−0.1570 (2)0.14203 (7)0.24089 (13)0.0412 (4)
H7−0.16600.17320.19700.049*
C8−0.2628 (3)0.09837 (9)0.21740 (16)0.0499 (4)
H8−0.34400.09970.15610.060*
C9−0.2499 (3)0.05245 (8)0.28383 (17)0.0520 (5)
H9−0.32390.02360.26680.062*
C10−0.1296 (3)0.04837 (7)0.37506 (16)0.0437 (4)
H10−0.12220.01740.41950.052*
C11−0.0204 (2)0.09189 (6)0.39817 (12)0.0304 (3)
C120.12180 (19)0.09758 (6)0.48990 (11)0.0288 (3)
C13−0.01516 (18)0.13617 (5)0.63622 (11)0.0258 (2)
H13−0.12890.14010.59570.031*
C14−0.03749 (18)0.13378 (6)0.76052 (11)0.0284 (3)
C15−0.1605 (2)0.16454 (6)0.81773 (13)0.0346 (3)
H15−0.24520.18970.78220.042*
C16−0.1410 (3)0.15208 (7)0.93502 (13)0.0428 (4)
H16−0.20980.16710.99460.051*
C17−0.0065 (2)0.11379 (8)0.95056 (13)0.0451 (4)
H170.03450.09761.02300.054*
C180.0584 (2)0.10234 (7)0.84277 (13)0.0367 (3)
H180.15220.07720.82800.044*
C19−0.3003 (3)0.02961 (9)0.7276 (2)0.0606 (6)
H19−0.27000.02620.64850.073*
C20−0.4307 (3)0.06263 (10)0.7669 (2)0.0666 (6)
H20−0.50940.08590.72080.080*
C21−0.4295 (3)0.05528 (12)0.8862 (3)0.0791 (9)
H21−0.50740.07280.93730.095*
C22−0.2990 (4)0.01844 (11)0.9176 (2)0.0767 (8)
H22−0.26860.00560.99480.092*
C23−0.2207 (4)0.00267 (9)0.8196 (2)0.0687 (7)
H23−0.1242−0.02280.81640.082*
C240.4551 (3)0.17375 (11)0.39497 (19)0.0616 (6)
H24A0.57730.17630.41420.074*
H24B0.41490.20690.36070.074*
H24C0.43350.14460.34260.074*
C250.01735 (19)0.23602 (6)0.58256 (12)0.0295 (3)
C26−0.2250 (3)0.28321 (8)0.5066 (2)0.0582 (5)
H26A−0.33690.27670.46940.070*
H26B−0.15640.30440.45810.070*
H26C−0.23850.30230.57620.070*
N10.36358 (17)0.16382 (6)0.49745 (12)0.0385 (3)
O10.06469 (15)0.08784 (4)0.60056 (9)0.0320 (2)
O20.25662 (16)0.06304 (5)0.47192 (10)0.0409 (3)
H2C0.34840.07730.49360.049*
O30.10650 (19)0.22437 (5)0.33645 (11)0.0487 (3)
O40.07972 (19)0.27824 (5)0.61256 (14)0.0553 (4)
O5−0.13909 (15)0.23198 (5)0.53094 (11)0.0406 (3)
Fe1−0.19791 (3)0.084076 (8)0.842289 (18)0.03124 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0290 (7)0.0467 (9)0.0460 (8)−0.0073 (7)−0.0002 (6)−0.0006 (7)
C20.0332 (7)0.0373 (8)0.0327 (7)−0.0035 (6)−0.0035 (5)0.0020 (6)
C30.0276 (6)0.0219 (6)0.0249 (5)−0.0009 (5)0.0025 (4)−0.0005 (4)
C40.0298 (6)0.0230 (6)0.0287 (6)−0.0015 (5)0.0054 (5)−0.0003 (5)
C50.0382 (7)0.0266 (6)0.0275 (6)−0.0022 (6)0.0072 (5)0.0023 (5)
C60.0387 (7)0.0281 (7)0.0253 (6)−0.0013 (6)0.0054 (5)−0.0010 (5)
C70.0518 (10)0.0428 (9)0.0287 (7)0.0018 (7)−0.0007 (6)0.0008 (6)
C80.0514 (11)0.0580 (11)0.0392 (8)−0.0047 (9)−0.0072 (7)−0.0075 (8)
C90.0543 (11)0.0458 (10)0.0553 (11)−0.0171 (9)−0.0026 (9)−0.0117 (8)
C100.0570 (10)0.0286 (8)0.0456 (9)−0.0097 (7)0.0026 (8)−0.0012 (6)
C110.0386 (7)0.0245 (6)0.0286 (6)−0.0016 (5)0.0053 (5)−0.0024 (5)
C120.0372 (7)0.0209 (6)0.0285 (6)0.0023 (5)0.0046 (5)−0.0001 (5)
C130.0297 (6)0.0206 (6)0.0273 (6)−0.0018 (5)0.0029 (5)0.0024 (4)
C140.0318 (7)0.0268 (6)0.0269 (6)−0.0043 (5)0.0036 (5)0.0020 (5)
C150.0434 (8)0.0256 (7)0.0355 (7)−0.0013 (6)0.0077 (6)−0.0029 (5)
C160.0577 (10)0.0400 (9)0.0316 (7)−0.0117 (8)0.0108 (7)−0.0087 (6)
C170.0525 (10)0.0547 (11)0.0278 (7)−0.0113 (8)−0.0008 (6)0.0069 (7)
C180.0320 (7)0.0431 (9)0.0349 (7)0.0003 (6)0.0019 (6)0.0098 (6)
C190.0717 (14)0.0498 (12)0.0620 (12)−0.0267 (10)0.0180 (10)−0.0215 (10)
C200.0466 (11)0.0551 (13)0.0970 (19)−0.0138 (10)−0.0048 (11)−0.0154 (12)
C210.0657 (15)0.0739 (17)0.103 (2)−0.0361 (13)0.0521 (15)−0.0357 (15)
C220.103 (2)0.0593 (14)0.0700 (15)−0.0363 (15)0.0245 (14)0.0153 (11)
C230.0789 (16)0.0283 (9)0.1009 (19)−0.0077 (10)0.0216 (14)−0.0013 (10)
C240.0436 (10)0.0817 (16)0.0623 (12)−0.0127 (10)0.0264 (9)−0.0172 (11)
C250.0339 (7)0.0238 (6)0.0311 (6)−0.0002 (5)0.0056 (5)0.0002 (5)
C260.0475 (11)0.0378 (10)0.0881 (16)0.0124 (8)−0.0049 (10)0.0137 (10)
N10.0281 (6)0.0417 (8)0.0465 (7)−0.0027 (5)0.0093 (5)−0.0054 (6)
O10.0481 (6)0.0197 (4)0.0289 (5)0.0020 (4)0.0072 (4)0.0034 (3)
O20.0459 (7)0.0315 (6)0.0457 (6)0.0122 (5)0.0054 (5)−0.0037 (5)
O30.0688 (9)0.0340 (6)0.0431 (6)−0.0140 (6)0.0023 (6)0.0134 (5)
O40.0585 (8)0.0255 (6)0.0798 (10)−0.0030 (6)−0.0130 (7)−0.0090 (6)
O50.0344 (6)0.0277 (5)0.0590 (7)0.0032 (4)−0.0034 (5)0.0062 (5)
Fe10.03617 (13)0.02629 (11)0.03231 (11)−0.00393 (8)0.01072 (8)−0.00053 (7)

Geometric parameters (Å, °)

C1—N11.462 (2)C15—H150.9800
C1—C21.508 (2)C16—C171.411 (3)
C1—H1A0.9700C16—Fe12.0428 (16)
C1—H1B0.9700C16—H160.9800
C2—C31.534 (2)C17—C181.425 (2)
C2—H2A0.9700C17—Fe12.0342 (18)
C2—H2B0.9700C17—H170.9800
C3—C251.5195 (19)C18—Fe12.0315 (16)
C3—C131.5557 (18)C18—H180.9800
C3—C41.5626 (18)C19—C231.388 (4)
C4—N11.4571 (19)C19—C201.399 (3)
C4—C51.534 (2)C19—Fe12.0380 (19)
C4—C121.5686 (19)C19—H190.9800
C5—O31.2102 (18)C20—C211.419 (4)
C5—C61.472 (2)C20—Fe12.029 (2)
C6—C111.386 (2)C20—H200.9800
C6—C71.388 (2)C21—C221.394 (4)
C7—C81.374 (3)C21—Fe12.023 (2)
C7—H70.9300C21—H210.9800
C8—C91.382 (3)C22—C231.394 (4)
C8—H80.9300C22—Fe12.032 (2)
C9—C101.384 (3)C22—H220.9800
C9—H90.9300C23—Fe12.040 (2)
C10—C111.386 (2)C23—H230.9800
C10—H100.9300C24—N11.459 (2)
C11—C121.503 (2)C24—H24A0.9600
C12—O21.3747 (18)C24—H24B0.9600
C12—O11.4251 (17)C24—H24C0.9600
C13—O11.4223 (16)C25—O41.1963 (19)
C13—C141.4897 (18)C25—O51.3248 (19)
C13—H130.9800C26—O51.453 (2)
C14—C181.419 (2)C26—H26A0.9600
C14—C151.421 (2)C26—H26B0.9600
C14—Fe12.0323 (13)C26—H26C0.9600
C15—C161.418 (2)O2—H2C0.8200
C15—Fe12.0372 (15)
N1—C1—C2102.88 (13)Fe1—C19—H19125.8
N1—C1—H1A111.2C19—C20—C21107.0 (2)
C2—C1—H1A111.2C19—C20—Fe170.21 (13)
N1—C1—H1B111.2C21—C20—Fe169.27 (13)
C2—C1—H1B111.2C19—C20—H20126.5
H1A—C1—H1B109.1C21—C20—H20126.5
C1—C2—C3103.66 (12)Fe1—C20—H20126.5
C1—C2—H2A111.0C22—C21—C20108.1 (2)
C3—C2—H2A111.0C22—C21—Fe170.23 (13)
C1—C2—H2B111.0C20—C21—Fe169.73 (12)
C3—C2—H2B111.0C22—C21—H21126.0
H2A—C2—H2B109.0C20—C21—H21126.0
C25—C3—C2109.92 (12)Fe1—C21—H21126.0
C25—C3—C13113.33 (11)C23—C22—C21107.8 (2)
C2—C3—C13114.28 (11)C23—C22—Fe170.31 (12)
C25—C3—C4113.32 (11)C21—C22—Fe169.56 (13)
C2—C3—C4102.72 (11)C23—C22—H22126.1
C13—C3—C4102.65 (10)C21—C22—H22126.1
N1—C4—C5116.85 (12)Fe1—C22—H22126.1
N1—C4—C3106.11 (11)C19—C23—C22108.8 (2)
C5—C4—C3115.08 (11)C19—C23—Fe170.02 (12)
N1—C4—C12110.34 (12)C22—C23—Fe169.67 (13)
C5—C4—C12104.43 (11)C19—C23—H23125.6
C3—C4—C12103.17 (10)C22—C23—H23125.6
O3—C5—C6126.98 (14)Fe1—C23—H23125.6
O3—C5—C4125.34 (14)N1—C24—H24A109.5
C6—C5—C4107.67 (11)N1—C24—H24B109.5
C11—C6—C7121.73 (15)H24A—C24—H24B109.5
C11—C6—C5110.64 (13)N1—C24—H24C109.5
C7—C6—C5127.58 (14)H24A—C24—H24C109.5
C8—C7—C6117.86 (16)H24B—C24—H24C109.5
C8—C7—H7121.1O4—C25—O5122.86 (15)
C6—C7—H7121.1O4—C25—C3124.32 (14)
C7—C8—C9120.77 (17)O5—C25—C3112.81 (12)
C7—C8—H8119.6O5—C26—H26A109.5
C9—C8—H8119.6O5—C26—H26B109.5
C8—C9—C10121.61 (17)H26A—C26—H26B109.5
C8—C9—H9119.2O5—C26—H26C109.5
C10—C9—H9119.2H26A—C26—H26C109.5
C9—C10—C11117.98 (16)H26B—C26—H26C109.5
C9—C10—H10121.0C4—N1—C24118.13 (15)
C11—C10—H10121.0C4—N1—C1108.77 (12)
C10—C11—C6120.03 (15)C24—N1—C1114.80 (15)
C10—C11—C12128.69 (14)C13—O1—C12107.04 (10)
C6—C11—C12111.27 (13)C12—O2—H2C109.5
O2—C12—O1108.41 (11)C25—O5—C26114.76 (14)
O2—C12—C11111.00 (12)C21—Fe1—C2041.00 (12)
O1—C12—C11113.09 (12)C21—Fe1—C18162.82 (11)
O2—C12—C4113.03 (12)C20—Fe1—C18153.91 (9)
O1—C12—C4106.52 (10)C21—Fe1—C2240.21 (13)
C11—C12—C4104.76 (11)C20—Fe1—C2268.19 (12)
O1—C13—C14109.66 (11)C18—Fe1—C22125.27 (11)
O1—C13—C3104.10 (10)C21—Fe1—C14155.48 (12)
C14—C13—C3114.86 (11)C20—Fe1—C14120.02 (9)
O1—C13—H13109.3C18—Fe1—C1440.87 (6)
C14—C13—H13109.3C22—Fe1—C14162.65 (11)
C3—C13—H13109.3C21—Fe1—C17126.00 (10)
C18—C14—C15107.79 (13)C20—Fe1—C17164.24 (10)
C18—C14—C13127.59 (13)C18—Fe1—C1741.03 (7)
C15—C14—C13124.61 (13)C22—Fe1—C17107.36 (10)
C18—C14—Fe169.53 (8)C14—Fe1—C1768.79 (6)
C15—C14—Fe169.76 (8)C21—Fe1—C15121.12 (10)
C13—C14—Fe1127.05 (10)C20—Fe1—C15108.87 (9)
C16—C15—C14108.25 (14)C18—Fe1—C1568.64 (7)
C16—C15—Fe169.87 (9)C22—Fe1—C15155.06 (10)
C14—C15—Fe169.39 (8)C14—Fe1—C1540.86 (6)
C16—C15—H15125.9C17—Fe1—C1568.37 (7)
C14—C15—H15125.9C21—Fe1—C1967.84 (10)
Fe1—C15—H15125.9C20—Fe1—C1940.24 (10)
C17—C16—C15107.91 (14)C18—Fe1—C19119.26 (8)
C17—C16—Fe169.42 (10)C22—Fe1—C1967.50 (11)
C15—C16—Fe169.44 (9)C14—Fe1—C19107.98 (8)
C17—C16—H16126.0C17—Fe1—C19153.65 (10)
C15—C16—H16126.0C15—Fe1—C19127.29 (9)
Fe1—C16—H16126.0C21—Fe1—C2367.31 (11)
C16—C17—C18108.28 (14)C20—Fe1—C2367.44 (11)
C16—C17—Fe170.08 (10)C18—Fe1—C23107.28 (9)
C18—C17—Fe169.39 (9)C22—Fe1—C2340.03 (11)
C16—C17—H17125.9C14—Fe1—C23125.93 (8)
C18—C17—H17125.9C17—Fe1—C23119.59 (10)
Fe1—C17—H17125.9C15—Fe1—C23163.76 (9)
C14—C18—C17107.77 (15)C19—Fe1—C2339.78 (11)
C14—C18—Fe169.60 (9)C21—Fe1—C16108.59 (9)
C17—C18—Fe169.59 (10)C20—Fe1—C16127.42 (9)
C14—C18—H18126.1C18—Fe1—C1668.68 (8)
C17—C18—H18126.1C22—Fe1—C16120.07 (9)
Fe1—C18—H18126.1C14—Fe1—C1668.74 (6)
C23—C19—C20108.3 (2)C17—Fe1—C1640.50 (8)
C23—C19—Fe170.20 (13)C15—Fe1—C1640.69 (6)
C20—C19—Fe169.55 (12)C19—Fe1—C16164.77 (10)
C23—C19—H19125.8C23—Fe1—C16154.08 (10)
C20—C19—H19125.8
N1—C1—C2—C3−40.15 (16)C21—C20—Fe1—C19118.0 (2)
C1—C2—C3—C25−89.90 (14)C19—C20—Fe1—C23−37.12 (15)
C1—C2—C3—C13141.37 (13)C21—C20—Fe1—C2380.86 (18)
C1—C2—C3—C431.00 (15)C19—C20—Fe1—C16167.58 (13)
C25—C3—C4—N1107.73 (13)C21—C20—Fe1—C16−74.44 (19)
C2—C3—C4—N1−10.81 (14)C14—C18—Fe1—C21−165.8 (3)
C13—C3—C4—N1−129.67 (11)C17—C18—Fe1—C21−46.7 (3)
C25—C3—C4—C5−23.13 (16)C14—C18—Fe1—C2051.6 (2)
C2—C3—C4—C5−141.67 (12)C17—C18—Fe1—C20170.7 (2)
C13—C3—C4—C599.47 (13)C14—C18—Fe1—C22165.77 (12)
C25—C3—C4—C12−136.22 (12)C17—C18—Fe1—C22−75.16 (15)
C2—C3—C4—C12105.25 (12)C17—C18—Fe1—C14119.07 (15)
C13—C3—C4—C12−13.62 (13)C14—C18—Fe1—C17−119.07 (15)
N1—C4—C5—O3−49.5 (2)C14—C18—Fe1—C15−37.90 (9)
C3—C4—C5—O375.95 (19)C17—C18—Fe1—C1581.18 (11)
C12—C4—C5—O3−171.71 (15)C14—C18—Fe1—C1983.87 (13)
N1—C4—C5—C6131.42 (13)C17—C18—Fe1—C19−157.05 (13)
C3—C4—C5—C6−103.11 (13)C14—C18—Fe1—C23125.43 (12)
C12—C4—C5—C69.24 (15)C17—C18—Fe1—C23−115.49 (13)
O3—C5—C6—C11177.09 (16)C14—C18—Fe1—C16−81.73 (10)
C4—C5—C6—C11−3.88 (16)C17—C18—Fe1—C1637.34 (11)
O3—C5—C6—C7−5.5 (3)C23—C22—Fe1—C21118.6 (3)
C4—C5—C6—C7173.49 (15)C23—C22—Fe1—C2080.45 (19)
C11—C6—C7—C80.4 (2)C21—C22—Fe1—C20−38.20 (16)
C5—C6—C7—C8−176.70 (16)C23—C22—Fe1—C18−74.0 (2)
C6—C7—C8—C90.7 (3)C21—C22—Fe1—C18167.40 (14)
C7—C8—C9—C10−0.8 (3)C23—C22—Fe1—C14−41.3 (4)
C8—C9—C10—C11−0.3 (3)C21—C22—Fe1—C14−160.0 (2)
C9—C10—C11—C61.4 (3)C23—C22—Fe1—C17−115.62 (18)
C9—C10—C11—C12−178.98 (17)C21—C22—Fe1—C17125.74 (16)
C7—C6—C11—C10−1.5 (2)C23—C22—Fe1—C15168.48 (19)
C5—C6—C11—C10176.04 (15)C21—C22—Fe1—C1549.8 (3)
C7—C6—C11—C12178.83 (14)C23—C22—Fe1—C1936.85 (17)
C5—C6—C11—C12−3.63 (17)C21—C22—Fe1—C19−81.80 (17)
C10—C11—C12—O267.4 (2)C21—C22—Fe1—C23−118.6 (3)
C6—C11—C12—O2−112.98 (14)C23—C22—Fe1—C16−157.91 (16)
C10—C11—C12—O1−54.7 (2)C21—C22—Fe1—C1683.44 (18)
C6—C11—C12—O1124.92 (13)C18—C14—Fe1—C21169.91 (19)
C10—C11—C12—C4−170.31 (16)C15—C14—Fe1—C2150.9 (2)
C6—C11—C12—C49.33 (16)C13—C14—Fe1—C21−67.8 (2)
N1—C4—C12—O2−16.34 (16)C18—C14—Fe1—C20−156.55 (12)
C5—C4—C12—O2110.01 (13)C15—C14—Fe1—C2084.43 (12)
C3—C4—C12—O2−129.34 (12)C13—C14—Fe1—C20−34.27 (16)
N1—C4—C12—O1102.61 (13)C15—C14—Fe1—C18−119.02 (13)
C5—C4—C12—O1−131.04 (12)C13—C14—Fe1—C18122.28 (17)
C3—C4—C12—O1−10.39 (14)C18—C14—Fe1—C22−42.3 (3)
N1—C4—C12—C11−137.32 (12)C15—C14—Fe1—C22−161.3 (3)
C5—C4—C12—C11−10.96 (14)C13—C14—Fe1—C2280.0 (3)
C3—C4—C12—C11109.68 (12)C18—C14—Fe1—C1737.98 (11)
C25—C3—C13—O1156.23 (11)C15—C14—Fe1—C17−81.04 (10)
C2—C3—C13—O1−76.78 (13)C13—C14—Fe1—C17160.26 (15)
C4—C3—C13—O133.64 (12)C18—C14—Fe1—C15119.02 (13)
C25—C3—C13—C14−83.85 (14)C13—C14—Fe1—C15−118.70 (16)
C2—C3—C13—C1443.14 (16)C18—C14—Fe1—C19−114.22 (12)
C4—C3—C13—C14153.56 (12)C15—C14—Fe1—C19126.75 (11)
O1—C13—C14—C1823.8 (2)C13—C14—Fe1—C198.06 (15)
C3—C13—C14—C18−92.97 (18)C18—C14—Fe1—C23−73.92 (14)
O1—C13—C14—C15−157.47 (14)C15—C14—Fe1—C23167.05 (13)
C3—C13—C14—C1585.74 (17)C13—C14—Fe1—C2348.36 (18)
O1—C13—C14—Fe1−67.80 (15)C18—C14—Fe1—C1681.57 (11)
C3—C13—C14—Fe1175.41 (10)C15—C14—Fe1—C16−37.45 (10)
C18—C14—C15—C16−0.10 (18)C13—C14—Fe1—C16−156.15 (15)
C13—C14—C15—C16−179.03 (13)C16—C17—Fe1—C21−75.88 (16)
Fe1—C14—C15—C1659.25 (11)C18—C17—Fe1—C21164.60 (14)
C18—C14—C15—Fe1−59.36 (11)C16—C17—Fe1—C20−45.2 (4)
C13—C14—C15—Fe1121.72 (14)C18—C17—Fe1—C20−164.8 (3)
C14—C15—C16—C170.01 (19)C16—C17—Fe1—C18119.52 (14)
Fe1—C15—C16—C1758.96 (12)C16—C17—Fe1—C22−116.25 (13)
C14—C15—C16—Fe1−58.95 (11)C18—C17—Fe1—C22124.22 (13)
C15—C16—C17—C180.1 (2)C16—C17—Fe1—C1481.68 (10)
Fe1—C16—C17—C1859.06 (12)C18—C17—Fe1—C14−37.84 (10)
C15—C16—C17—Fe1−58.97 (12)C16—C17—Fe1—C1537.64 (10)
C15—C14—C18—C170.16 (18)C18—C17—Fe1—C15−81.88 (11)
C13—C14—C18—C17179.04 (14)C16—C17—Fe1—C19169.54 (17)
Fe1—C14—C18—C17−59.34 (12)C18—C17—Fe1—C1950.0 (2)
C15—C14—C18—Fe159.49 (11)C16—C17—Fe1—C23−158.08 (11)
C13—C14—C18—Fe1−121.62 (15)C18—C17—Fe1—C2382.39 (13)
C16—C17—C18—C14−0.2 (2)C18—C17—Fe1—C16−119.52 (14)
Fe1—C17—C18—C1459.34 (11)C16—C15—Fe1—C2182.47 (15)
C16—C17—C18—Fe1−59.49 (13)C14—C15—Fe1—C21−157.90 (12)
C23—C19—C20—C210.0 (2)C16—C15—Fe1—C20125.98 (13)
Fe1—C19—C20—C21−59.75 (15)C14—C15—Fe1—C20−114.40 (11)
C23—C19—C20—Fe159.70 (16)C16—C15—Fe1—C18−81.72 (11)
C19—C20—C21—C220.3 (3)C14—C15—Fe1—C1837.91 (9)
Fe1—C20—C21—C22−60.03 (17)C16—C15—Fe1—C2247.3 (3)
C19—C20—C21—Fe160.35 (15)C14—C15—Fe1—C22166.9 (2)
C20—C21—C22—C23−0.5 (3)C16—C15—Fe1—C14−119.63 (14)
Fe1—C21—C22—C23−60.19 (16)C16—C15—Fe1—C17−37.47 (11)
C20—C21—C22—Fe159.72 (16)C14—C15—Fe1—C1782.15 (10)
C20—C19—C23—C22−0.2 (3)C16—C15—Fe1—C19167.07 (12)
Fe1—C19—C23—C2259.05 (17)C14—C15—Fe1—C19−73.31 (13)
C20—C19—C23—Fe1−59.30 (15)C16—C15—Fe1—C23−160.1 (3)
C21—C22—C23—C190.4 (3)C14—C15—Fe1—C23−40.4 (4)
Fe1—C22—C23—C19−59.27 (16)C14—C15—Fe1—C16119.63 (14)
C21—C22—C23—Fe159.71 (16)C23—C19—Fe1—C21−80.70 (18)
C2—C3—C25—O49.2 (2)C20—C19—Fe1—C2138.73 (18)
C13—C3—C25—O4138.41 (17)C23—C19—Fe1—C20−119.4 (2)
C4—C3—C25—O4−105.12 (18)C23—C19—Fe1—C1881.91 (15)
C2—C3—C25—O5−171.14 (12)C20—C19—Fe1—C18−158.67 (15)
C13—C3—C25—O5−41.90 (16)C23—C19—Fe1—C22−37.07 (16)
C4—C3—C25—O574.57 (15)C20—C19—Fe1—C2282.36 (18)
C5—C4—N1—C24−17.7 (2)C23—C19—Fe1—C14125.06 (14)
C3—C4—N1—C24−147.54 (16)C20—C19—Fe1—C14−115.51 (16)
C12—C4—N1—C24101.35 (17)C23—C19—Fe1—C1746.7 (2)
C5—C4—N1—C1115.47 (15)C20—C19—Fe1—C17166.12 (17)
C3—C4—N1—C1−14.38 (16)C23—C19—Fe1—C15166.27 (13)
C12—C4—N1—C1−125.48 (13)C20—C19—Fe1—C15−74.30 (18)
C2—C1—N1—C434.20 (17)C20—C19—Fe1—C23119.4 (2)
C2—C1—N1—C24169.08 (16)C23—C19—Fe1—C16−160.0 (3)
C14—C13—O1—C12−165.76 (11)C20—C19—Fe1—C16−40.6 (4)
C3—C13—O1—C12−42.39 (13)C19—C23—Fe1—C2182.13 (17)
O2—C12—O1—C13155.22 (12)C22—C23—Fe1—C21−37.89 (19)
C11—C12—O1—C13−81.24 (14)C19—C23—Fe1—C2037.54 (15)
C4—C12—O1—C1333.29 (14)C22—C23—Fe1—C20−82.5 (2)
O4—C25—O5—C263.9 (2)C19—C23—Fe1—C18−115.24 (14)
C3—C25—O5—C26−175.77 (15)C22—C23—Fe1—C18124.75 (18)
C22—C21—Fe1—C20118.9 (2)C19—C23—Fe1—C22120.0 (2)
C22—C21—Fe1—C18−37.1 (4)C19—C23—Fe1—C14−74.06 (16)
C20—C21—Fe1—C18−156.0 (3)C22—C23—Fe1—C14165.93 (16)
C20—C21—Fe1—C22−118.9 (2)C19—C23—Fe1—C17−158.19 (13)
C22—C21—Fe1—C14165.75 (18)C22—C23—Fe1—C1781.80 (19)
C20—C21—Fe1—C1446.8 (3)C19—C23—Fe1—C15−42.5 (4)
C22—C21—Fe1—C17−73.26 (18)C22—C23—Fe1—C15−162.5 (3)
C20—C21—Fe1—C17167.82 (14)C22—C23—Fe1—C19−120.0 (2)
C22—C21—Fe1—C15−157.89 (14)C19—C23—Fe1—C16168.13 (17)
C20—C21—Fe1—C1583.18 (16)C22—C23—Fe1—C1648.1 (3)
C22—C21—Fe1—C1980.90 (17)C17—C16—Fe1—C21124.13 (14)
C20—C21—Fe1—C19−38.03 (15)C15—C16—Fe1—C21−116.43 (15)
C22—C21—Fe1—C2337.71 (17)C17—C16—Fe1—C20165.95 (13)
C20—C21—Fe1—C23−81.21 (17)C15—C16—Fe1—C20−74.62 (15)
C22—C21—Fe1—C16−114.90 (16)C17—C16—Fe1—C18−37.82 (10)
C20—C21—Fe1—C16126.18 (15)C15—C16—Fe1—C1881.62 (11)
C19—C20—Fe1—C21−118.0 (2)C17—C16—Fe1—C2281.54 (15)
C19—C20—Fe1—C1846.2 (3)C15—C16—Fe1—C22−159.02 (14)
C21—C20—Fe1—C18164.15 (19)C17—C16—Fe1—C14−81.83 (10)
C19—C20—Fe1—C22−80.49 (17)C15—C16—Fe1—C1437.61 (10)
C21—C20—Fe1—C2237.49 (16)C15—C16—Fe1—C17119.44 (14)
C19—C20—Fe1—C1482.48 (16)C17—C16—Fe1—C15−119.44 (14)
C21—C20—Fe1—C14−159.54 (15)C17—C16—Fe1—C19−162.1 (3)
C19—C20—Fe1—C17−156.9 (3)C15—C16—Fe1—C19−42.7 (3)
C21—C20—Fe1—C17−38.9 (4)C17—C16—Fe1—C2348.0 (2)
C19—C20—Fe1—C15125.96 (14)C15—C16—Fe1—C23167.39 (19)
C21—C20—Fe1—C15−116.06 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O4i0.932.463.157 (2)131
C15—H15···O3ii0.982.523.303 (2)137
C16—H16···O4ii0.982.593.547 (2)166
C13—H13···O50.982.402.820 (2)105
C24—H24B···O30.962.423.014 (3)120
O2—H2C···N10.822.152.6414 (19)119
C2—H2A···O40.972.422.761 (2)100

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2949).

References

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