Literature DB >> 21583045

Methyl 5-ferrocenyl-5a-hydr-oxy-1-methyl-10-oxo-2,3,3a,4,5a,10-hexa-hydro-1H-indeno[1,2:2',3']furo[3',4'-b]pyrrole-3a-carboxyl-ate.

E Theboral Sugi Kamala, S Nirmala, L Sudha, S Kathiravan, R Raghunathan.   

Abstract

In the title compound, [Fe(C(5)H(5))(C(21)H(20)NO(5))], the pyrrolidine and cyclo-penta-none rings exhibit a twist conformation. The pyrrolidine ring is almost perpendicular to the cyclo-penta-none ring, making a dihedral angle of 81.91 (6)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond and C-H⋯O inter-actions. The crystal structure is stabilized by inter-molecular C-H⋯O inter-actions.

Entities:  

Year:  2009        PMID： 21583045      PMCID： PMC2969822          DOI： 10.1107/S1600536809018583

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

[Fe(C5H5)(C21H20NO5)] M = 487.32 Monoclinic, 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 ▶) 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 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: APEX2 and SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). 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
[Fe(C5H5)(C21H20NO5)]F(000) = 1016
Mr = 487.32Dx = 1.434 Mg m−3
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 mm−1
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
Bruker Kappa APEXII diffractometer7917 independent reflections
Radiation source: fine-focus sealed tube6016 reflections with I > 2σ(I)
graphiteRint = 0.028
ω and φ 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 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 Å−3
0 restraintsΔρmin = −0.35 e Å−3
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.
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)
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)
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)
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
Table 1

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) ; (ii) .

  4 in total

Review 1.  Bioorganometallic chemistry of ferrocene.

Authors:  Dave R van Staveren; Nils Metzler-Nolte
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

2.  Recent applications of chiral ferrocene ligands in asymmetric catalysis.

Authors:  Ramón Gómez Arrayás; Javier Adrio; Juan Carlos Carretero
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

3.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  4 in total

1.  4'-Ferrocenyl-1'-methylacenapthylene-1-spiro-2'-pyrrolidine-3'-spiro-2''-indane-2,1'',3''(1H)-trione.

Authors:  B Gunasekaran; S Kathiravan; R Raghunathan; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-25

2.  19-Ferrocenyl-18-oxa-8,16-diaza-penta-cyclo-[8.6.3.0.0.0]nona-deca-2(7),3,5-triene-9,17-dione.

Authors:  B Gunasekaran; S Kathiravan; R Raghunathan; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-10

3.  3-(Ferrocen-1-ylcarbon-yl)-1-methyl-4-(4-methyl-phen-yl)spiro-[pyrrolidine-2,11'-indeno-[1,2-b]quinoxaline].

Authors:  B Vijayakumar; D Gavaskar; T Srinivasan; R Raghunathan; D Velmurugan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-15

4.  4-Ferrocenyl-1-methyl-3-benzoyl-spiro-[pyrrolidine-2,11'-indeno-[1,2-b]quinoxaline].

Authors:  B Vijayakumar; A R Sureshbabu; D Gavaskar; R Raghunathan; D Velmurugan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-30
  4 in total

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