metal-organic compounds
3-(Ferrocen-1-ylcarbonyl)-1-methyl-4-(4-methylphenyl)spiro[pyrrolidine-2,11′-indeno[1,2-b]quinoxaline]
aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Maraimalai (Guindy) Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai (Guindy) Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com
In the title compound, [Fe(C5H5)(C32H26N3O)], the pyrrolidine ring adopts a twist conformation. The indeno–quinoxaline ring system [86.44 (5)°], the methylphenyl ring [86.06 (7)°] and the ferrocene rings [82.00 (7) and 83.95 (9)°] are almost perpendicular to the pyrrolidine ring. The two cyclopentadienyl rings adopt an eclipsed conformation. The features C—H⋯N interactions.
Related literature
For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004); Biot et al. (2004); Fouda et al. (2007). For related structures, see: Satis Kumar et al.(2007); Kamala et al. (2009); Gunasekaran et al. (2010); For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812036951/bt6825sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036951/bt6825Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812036951/bt6825Isup4.mol
Ninhydrin (1 mM) and 1, 2-phenylenediamine (1 mM) were mixed and stirred with 10mL of methanol for 10 min. To this mixture 1 mM of Sarcosine and 1 mM of ferrocene derived dipolarophile were added and was refluxed up to the end of the reaction as observed by TLC. The solvent content from the mixture was removed under reduced pressure and the crude product was obtained. Using
the crude extract was purified by 4:1 ratio of petroleum ether and ethyl acetate. Finally, single crystals suitable for the X-ray diffraction were obtained by slow evaporation at room temperature.Hydrogen atoms were placed in calculated positions with C—H ranging from = 0.93Å to 0.98Å and refined using the riding model approximation with Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl).
Ferrocene attached compounds have prominent biological activities like antitumor (Jaouen et al., 2004), antimalarial and antifungal (Biot et al., 2004), and antibacterial (Fouda et al., 2007) and find applications in medicinal chemistry. In this background, X-ray study of the title compound was carried out to obtain the information of molecular conformations and crystal packing in the solid state.
X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles of titled compound agree with those observed in other ferrocene derivative 4'-Ferrocenyl-3'- 4-methoxybenzoyl)-1'-methylspiro[1H-indole-3(2H), 2'-pyrrolidin]-2-one (Satis Kumar et al., 2007). The dihedral angle between indeno-quinoxaline ring system and the pyrrolidine ring is 87.84 (7)° and the dihedral angle between pyrrolidine ring and the phenyl ring is 86.06 (9) °. The dihedral angle between pyrrolidine ring and the ferrocene rings are 81.00 (10)° and 83.94 (12)°. This clearly shows that the indeno-quinoxaline ring system, the phenyl and ferrocene rings are almost perpendicular to the pyrrolidine ring.
The pyrrolidine ring adopts a twisted conformation with the puckering parameters q2 and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, δ, (Nardelli, 1983) as follows: q2 = 0.3858 (16) Å, φ = 343.1 (3)° and Δ2 (C16) = 2.13 (15)°. In the ferrocene, Cg3 and Cg4 are the centroids of the C27—C31 and C32—C36 rings, respectively. Fe1—Cg3 and Fe1—Cg4 distances are 1.6430 (8) and 1.6495 (10) Å, respectively and the Cg3—Fe1—Cg4 angle is 177.74 (6)°. In addition to the van der Waals interactions, the crystal packing is stabilized by C—H···N interaction (Table. 1 & Fig. 2).
For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004); Biot et al. (2004); Fouda et al. (2007). For related structures, see: Satis Kumar et al.(2007); Kamala et al. (2009); Gunasekaran et al. (2010); For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).[Fe(C5H5)(C32H26N3O)] | F(000) = 1232 |
Mr = 589.50 | Dx = 1.359 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7145 reflections |
a = 11.5966 (3) Å | θ = 2.0–28.3° |
b = 11.8658 (3) Å | µ = 0.56 mm−1 |
c = 20.9383 (6) Å | T = 293 K |
β = 90.616 (2)° | Block, brown |
V = 2881.01 (13) Å3 | 0.2 × 0.2 × 0.2 mm |
Z = 4 |
Bruker SMART APEXII area-detector diffractometer | 5247 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 28.3°, θmin = 2.0° |
ω and φ scans | h = −14→15 |
26509 measured reflections | k = −15→14 |
7145 independent reflections | l = −27→25 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.5923P] where P = (Fo2 + 2Fc2)/3 |
7145 reflections | (Δ/σ)max = 0.023 |
381 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[Fe(C5H5)(C32H26N3O)] | V = 2881.01 (13) Å3 |
Mr = 589.50 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.5966 (3) Å | µ = 0.56 mm−1 |
b = 11.8658 (3) Å | T = 293 K |
c = 20.9383 (6) Å | 0.2 × 0.2 × 0.2 mm |
β = 90.616 (2)° |
Bruker SMART APEXII area-detector diffractometer | 5247 reflections with I > 2σ(I) |
26509 measured reflections | Rint = 0.026 |
7145 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.26 e Å−3 |
7145 reflections | Δρmin = −0.31 e Å−3 |
381 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.29739 (19) | 0.35976 (18) | −0.10411 (9) | 0.0570 (5) | |
H1 | 0.2331 | 0.4050 | −0.0976 | 0.068* | |
C2 | 0.3437 (2) | 0.3508 (2) | −0.16349 (10) | 0.0716 (7) | |
H2 | 0.3110 | 0.3904 | −0.1975 | 0.086* | |
C3 | 0.4399 (2) | 0.2825 (2) | −0.17355 (11) | 0.0776 (8) | |
H3 | 0.4719 | 0.2789 | −0.2141 | 0.093* | |
C4 | 0.4876 (2) | 0.2215 (2) | −0.12547 (11) | 0.0718 (7) | |
H4 | 0.5502 | 0.1747 | −0.1333 | 0.086* | |
C5 | 0.44203 (16) | 0.22899 (17) | −0.06319 (9) | 0.0527 (5) | |
C6 | 0.34719 (15) | 0.30038 (15) | −0.05269 (8) | 0.0461 (4) | |
C7 | 0.35581 (13) | 0.26030 (14) | 0.05261 (8) | 0.0378 (3) | |
C8 | 0.45054 (14) | 0.18715 (15) | 0.04184 (9) | 0.0447 (4) | |
C9 | 0.49029 (15) | 0.14277 (15) | 0.10323 (9) | 0.0473 (4) | |
C10 | 0.42069 (14) | 0.18700 (14) | 0.15109 (8) | 0.0412 (4) | |
C11 | 0.32625 (13) | 0.26329 (13) | 0.12383 (7) | 0.0357 (3) | |
C12 | 0.44572 (16) | 0.16378 (16) | 0.21433 (9) | 0.0524 (4) | |
H12 | 0.4015 | 0.1947 | 0.2467 | 0.063* | |
C13 | 0.53779 (19) | 0.09358 (19) | 0.22876 (12) | 0.0669 (6) | |
H13 | 0.5544 | 0.0764 | 0.2712 | 0.080* | |
C14 | 0.6054 (2) | 0.0487 (2) | 0.18112 (13) | 0.0735 (7) | |
H14 | 0.6666 | 0.0016 | 0.1919 | 0.088* | |
C15 | 0.58319 (18) | 0.07298 (18) | 0.11806 (12) | 0.0659 (6) | |
H15 | 0.6292 | 0.0435 | 0.0860 | 0.079* | |
C16 | 0.19757 (12) | 0.22576 (13) | 0.13323 (7) | 0.0335 (3) | |
H16 | 0.1661 | 0.2027 | 0.0916 | 0.040* | |
C17 | 0.13242 (14) | 0.33248 (14) | 0.15504 (8) | 0.0384 (4) | |
H17 | 0.1192 | 0.3268 | 0.2011 | 0.046* | |
C18 | 0.21749 (15) | 0.42714 (14) | 0.14355 (8) | 0.0414 (4) | |
H18A | 0.2111 | 0.4552 | 0.1001 | 0.050* | |
H18B | 0.2053 | 0.4890 | 0.1730 | 0.050* | |
C19 | 0.42792 (17) | 0.44471 (16) | 0.14190 (10) | 0.0530 (5) | |
H19A | 0.4262 | 0.4674 | 0.0979 | 0.080* | |
H19B | 0.4974 | 0.4032 | 0.1505 | 0.080* | |
H19C | 0.4257 | 0.5103 | 0.1687 | 0.080* | |
C20 | 0.01671 (14) | 0.34623 (14) | 0.12153 (8) | 0.0395 (4) | |
C21 | −0.08575 (16) | 0.34224 (17) | 0.15446 (9) | 0.0530 (5) | |
H21 | −0.0841 | 0.3338 | 0.1986 | 0.064* | |
C22 | −0.19103 (16) | 0.35058 (18) | 0.12277 (11) | 0.0594 (5) | |
H22 | −0.2587 | 0.3457 | 0.1461 | 0.071* | |
C23 | −0.19783 (15) | 0.36583 (15) | 0.05778 (10) | 0.0501 (4) | |
C24 | −0.09542 (16) | 0.37090 (16) | 0.02483 (9) | 0.0500 (4) | |
H24 | −0.0974 | 0.3811 | −0.0192 | 0.060* | |
C25 | 0.01009 (15) | 0.36115 (15) | 0.05584 (8) | 0.0457 (4) | |
H25 | 0.0776 | 0.3647 | 0.0323 | 0.055* | |
C26 | 0.18900 (13) | 0.12623 (14) | 0.17858 (7) | 0.0352 (3) | |
C27 | 0.20428 (13) | 0.01427 (14) | 0.15034 (7) | 0.0357 (3) | |
C28 | 0.20015 (15) | −0.08985 (14) | 0.18424 (9) | 0.0429 (4) | |
H28 | 0.1963 | −0.0982 | 0.2283 | 0.051* | |
C29 | 0.20304 (17) | −0.17801 (16) | 0.13901 (10) | 0.0535 (5) | |
H29 | 0.2013 | −0.2547 | 0.1482 | 0.064* | |
C30 | 0.20898 (17) | −0.13008 (16) | 0.07734 (9) | 0.0527 (5) | |
H30 | 0.2115 | −0.1699 | 0.0391 | 0.063* | |
C31 | 0.21043 (14) | −0.01244 (14) | 0.08348 (8) | 0.0408 (4) | |
H31 | 0.2146 | 0.0392 | 0.0502 | 0.049* | |
C32 | −0.07832 (18) | 0.0154 (3) | 0.14632 (14) | 0.0808 (8) | |
H32 | −0.0782 | 0.0858 | 0.1659 | 0.097* | |
C33 | −0.07821 (18) | −0.0055 (2) | 0.08054 (12) | 0.0733 (7) | |
H33 | −0.0779 | 0.0487 | 0.0485 | 0.088* | |
C34 | −0.0786 (2) | −0.1200 (3) | 0.07176 (14) | 0.0866 (8) | |
H34 | −0.0791 | −0.1567 | 0.0325 | 0.104* | |
C35 | −0.0781 (2) | −0.1716 (3) | 0.1306 (2) | 0.0998 (11) | |
H35 | −0.0775 | −0.2490 | 0.1378 | 0.120* | |
C36 | −0.0786 (2) | −0.0890 (4) | 0.17706 (14) | 0.0946 (10) | |
H36 | −0.0790 | −0.1008 | 0.2210 | 0.114* | |
C37 | −0.31185 (17) | 0.3780 (2) | 0.02292 (12) | 0.0678 (6) | |
H37A | −0.3713 | 0.3418 | 0.0470 | 0.102* | |
H37B | −0.3068 | 0.3433 | −0.0184 | 0.102* | |
H37C | −0.3299 | 0.4565 | 0.0179 | 0.102* | |
N1 | 0.30156 (12) | 0.31494 (12) | 0.00747 (6) | 0.0426 (3) | |
N2 | 0.49441 (14) | 0.16877 (15) | −0.01466 (8) | 0.0561 (4) | |
N3 | 0.32874 (11) | 0.37402 (11) | 0.15487 (6) | 0.0384 (3) | |
O1 | 0.17339 (11) | 0.13915 (11) | 0.23535 (5) | 0.0502 (3) | |
Fe1 | 0.06387 (2) | −0.07469 (2) | 0.123016 (11) | 0.04181 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0695 (13) | 0.0608 (12) | 0.0408 (10) | −0.0229 (10) | 0.0043 (9) | −0.0020 (9) |
C2 | 0.0903 (17) | 0.0848 (17) | 0.0399 (11) | −0.0422 (14) | 0.0044 (10) | −0.0026 (11) |
C3 | 0.0872 (17) | 0.103 (2) | 0.0433 (12) | −0.0423 (15) | 0.0236 (11) | −0.0244 (13) |
C4 | 0.0661 (14) | 0.0919 (18) | 0.0579 (14) | −0.0252 (13) | 0.0249 (11) | −0.0307 (13) |
C5 | 0.0510 (11) | 0.0600 (12) | 0.0476 (10) | −0.0217 (9) | 0.0151 (8) | −0.0189 (9) |
C6 | 0.0517 (10) | 0.0489 (10) | 0.0380 (9) | −0.0218 (8) | 0.0080 (7) | −0.0086 (7) |
C7 | 0.0373 (8) | 0.0370 (8) | 0.0393 (9) | −0.0097 (7) | 0.0073 (6) | −0.0064 (7) |
C8 | 0.0378 (9) | 0.0427 (9) | 0.0537 (10) | −0.0075 (7) | 0.0089 (7) | −0.0114 (8) |
C9 | 0.0369 (9) | 0.0424 (10) | 0.0628 (12) | −0.0022 (7) | 0.0026 (8) | −0.0088 (8) |
C10 | 0.0355 (8) | 0.0385 (9) | 0.0496 (10) | −0.0034 (7) | −0.0016 (7) | −0.0036 (7) |
C11 | 0.0356 (8) | 0.0368 (8) | 0.0348 (8) | −0.0032 (6) | 0.0010 (6) | −0.0023 (6) |
C12 | 0.0497 (10) | 0.0536 (11) | 0.0538 (11) | 0.0018 (8) | −0.0090 (8) | −0.0014 (9) |
C13 | 0.0622 (13) | 0.0615 (13) | 0.0765 (15) | 0.0061 (10) | −0.0222 (11) | 0.0043 (11) |
C14 | 0.0544 (13) | 0.0641 (14) | 0.1016 (19) | 0.0161 (11) | −0.0182 (12) | −0.0036 (13) |
C15 | 0.0484 (11) | 0.0575 (13) | 0.0917 (18) | 0.0102 (9) | 0.0034 (11) | −0.0122 (11) |
C16 | 0.0339 (8) | 0.0361 (8) | 0.0305 (8) | −0.0021 (6) | 0.0011 (6) | −0.0018 (6) |
C17 | 0.0409 (9) | 0.0408 (9) | 0.0335 (8) | 0.0033 (7) | 0.0032 (6) | −0.0011 (7) |
C18 | 0.0475 (9) | 0.0357 (9) | 0.0410 (9) | 0.0025 (7) | −0.0014 (7) | −0.0051 (7) |
C19 | 0.0515 (11) | 0.0469 (10) | 0.0606 (12) | −0.0133 (8) | −0.0008 (9) | −0.0063 (9) |
C20 | 0.0394 (8) | 0.0360 (8) | 0.0432 (9) | 0.0020 (7) | 0.0048 (7) | 0.0002 (7) |
C21 | 0.0468 (10) | 0.0617 (12) | 0.0506 (11) | 0.0095 (9) | 0.0104 (8) | 0.0096 (9) |
C22 | 0.0385 (10) | 0.0653 (13) | 0.0747 (14) | 0.0055 (9) | 0.0139 (9) | 0.0093 (11) |
C23 | 0.0394 (9) | 0.0400 (10) | 0.0709 (13) | 0.0003 (7) | −0.0035 (8) | −0.0021 (9) |
C24 | 0.0492 (10) | 0.0511 (11) | 0.0497 (10) | −0.0014 (8) | −0.0039 (8) | −0.0026 (8) |
C25 | 0.0383 (9) | 0.0532 (11) | 0.0456 (10) | −0.0015 (8) | 0.0033 (7) | −0.0006 (8) |
C26 | 0.0337 (8) | 0.0400 (9) | 0.0318 (8) | −0.0031 (6) | 0.0002 (6) | −0.0008 (6) |
C27 | 0.0333 (8) | 0.0392 (9) | 0.0347 (8) | −0.0015 (6) | −0.0013 (6) | 0.0011 (6) |
C28 | 0.0423 (9) | 0.0427 (9) | 0.0436 (9) | 0.0008 (7) | −0.0034 (7) | 0.0065 (7) |
C29 | 0.0602 (12) | 0.0362 (10) | 0.0641 (12) | 0.0060 (8) | 0.0006 (9) | 0.0032 (8) |
C30 | 0.0615 (12) | 0.0460 (11) | 0.0508 (11) | 0.0047 (9) | 0.0035 (9) | −0.0112 (8) |
C31 | 0.0436 (9) | 0.0427 (9) | 0.0362 (8) | 0.0006 (7) | 0.0044 (7) | 0.0006 (7) |
C32 | 0.0390 (11) | 0.099 (2) | 0.105 (2) | 0.0058 (12) | 0.0031 (12) | −0.0299 (17) |
C33 | 0.0480 (12) | 0.0911 (18) | 0.0804 (16) | 0.0039 (11) | −0.0125 (11) | 0.0230 (14) |
C34 | 0.0658 (15) | 0.100 (2) | 0.093 (2) | −0.0099 (14) | −0.0330 (14) | −0.0246 (17) |
C35 | 0.0642 (16) | 0.0845 (19) | 0.150 (3) | −0.0357 (14) | −0.0271 (18) | 0.036 (2) |
C36 | 0.0426 (12) | 0.167 (3) | 0.0742 (17) | −0.0171 (16) | 0.0051 (11) | 0.032 (2) |
C37 | 0.0438 (11) | 0.0635 (13) | 0.0959 (17) | 0.0014 (10) | −0.0121 (10) | −0.0107 (12) |
N1 | 0.0465 (8) | 0.0462 (8) | 0.0352 (7) | −0.0094 (6) | 0.0064 (6) | −0.0033 (6) |
N2 | 0.0477 (9) | 0.0622 (10) | 0.0588 (10) | −0.0089 (8) | 0.0153 (7) | −0.0201 (8) |
N3 | 0.0403 (7) | 0.0357 (7) | 0.0392 (7) | −0.0039 (6) | −0.0005 (6) | −0.0054 (6) |
O1 | 0.0692 (8) | 0.0498 (7) | 0.0319 (6) | −0.0028 (6) | 0.0060 (5) | −0.0001 (5) |
Fe1 | 0.04165 (15) | 0.04181 (15) | 0.04185 (15) | −0.00598 (10) | −0.00464 (10) | 0.00020 (10) |
C1—C2 | 1.364 (3) | C20—C25 | 1.388 (2) |
C1—C6 | 1.406 (3) | C21—C22 | 1.387 (3) |
C1—H1 | 0.9300 | C21—H21 | 0.9300 |
C2—C3 | 1.398 (4) | C22—C23 | 1.374 (3) |
C2—H2 | 0.9300 | C22—H22 | 0.9300 |
C3—C4 | 1.353 (4) | C23—C24 | 1.381 (3) |
C3—H3 | 0.9300 | C23—C37 | 1.510 (3) |
C4—C5 | 1.415 (3) | C24—C25 | 1.384 (2) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C5—N2 | 1.378 (3) | C25—H25 | 0.9300 |
C5—C6 | 1.407 (3) | C26—O1 | 1.2140 (19) |
C6—N1 | 1.382 (2) | C26—C27 | 1.466 (2) |
C7—N1 | 1.303 (2) | C27—C28 | 1.426 (2) |
C7—C8 | 1.420 (2) | C27—C31 | 1.438 (2) |
C7—C11 | 1.534 (2) | C27—Fe1 | 2.0181 (15) |
C8—N2 | 1.311 (2) | C28—C29 | 1.412 (3) |
C8—C9 | 1.459 (3) | C28—Fe1 | 2.0321 (17) |
C9—C15 | 1.391 (3) | C28—H28 | 0.9300 |
C9—C10 | 1.396 (2) | C29—C30 | 1.413 (3) |
C10—C12 | 1.380 (2) | C29—Fe1 | 2.0513 (19) |
C10—C11 | 1.527 (2) | C29—H29 | 0.9300 |
C11—N3 | 1.466 (2) | C30—C31 | 1.402 (3) |
C11—C16 | 1.572 (2) | C30—Fe1 | 2.053 (2) |
C12—C13 | 1.385 (3) | C30—H30 | 0.9300 |
C12—H12 | 0.9300 | C31—Fe1 | 2.0372 (17) |
C13—C14 | 1.382 (3) | C31—H31 | 0.9300 |
C13—H13 | 0.9300 | C32—C33 | 1.400 (3) |
C14—C15 | 1.373 (3) | C32—C36 | 1.396 (4) |
C14—H14 | 0.9300 | C32—Fe1 | 2.029 (2) |
C15—H15 | 0.9300 | C32—H32 | 0.9300 |
C16—C26 | 1.519 (2) | C33—C34 | 1.371 (4) |
C16—C17 | 1.546 (2) | C33—Fe1 | 2.037 (2) |
C16—H16 | 0.9800 | C33—H33 | 0.9300 |
C17—C18 | 1.516 (2) | C34—C35 | 1.375 (4) |
C17—C20 | 1.516 (2) | C34—Fe1 | 2.033 (2) |
C17—H17 | 0.9800 | C34—H34 | 0.9300 |
C18—N3 | 1.453 (2) | C35—C36 | 1.382 (5) |
C18—H18A | 0.9700 | C35—Fe1 | 2.016 (2) |
C18—H18B | 0.9700 | C35—H35 | 0.9300 |
C19—N3 | 1.452 (2) | C36—Fe1 | 2.019 (2) |
C19—H19A | 0.9600 | C36—H36 | 0.9300 |
C19—H19B | 0.9600 | C37—H37A | 0.9600 |
C19—H19C | 0.9600 | C37—H37B | 0.9600 |
C20—C21 | 1.381 (2) | C37—H37C | 0.9600 |
C2—C1—C6 | 119.8 (2) | C30—C29—C28 | 108.45 (16) |
C2—C1—H1 | 120.1 | C30—C29—Fe1 | 69.90 (11) |
C6—C1—H1 | 120.1 | C28—C29—Fe1 | 69.05 (10) |
C1—C2—C3 | 120.3 (2) | C30—C29—H29 | 125.8 |
C1—C2—H2 | 119.8 | C28—C29—H29 | 125.8 |
C3—C2—H2 | 119.8 | Fe1—C29—H29 | 126.9 |
C4—C3—C2 | 121.2 (2) | C31—C30—C29 | 108.52 (16) |
C4—C3—H3 | 119.4 | C31—C30—Fe1 | 69.37 (10) |
C2—C3—H3 | 119.4 | C29—C30—Fe1 | 69.81 (11) |
C3—C4—C5 | 119.9 (2) | C31—C30—H30 | 125.7 |
C3—C4—H4 | 120.0 | C29—C30—H30 | 125.7 |
C5—C4—H4 | 120.0 | Fe1—C30—H30 | 126.7 |
N2—C5—C6 | 122.42 (16) | C30—C31—C27 | 107.94 (15) |
N2—C5—C4 | 118.8 (2) | C30—C31—Fe1 | 70.55 (11) |
C6—C5—C4 | 118.8 (2) | C27—C31—Fe1 | 68.52 (9) |
N1—C6—C1 | 118.50 (18) | C30—C31—H31 | 126.0 |
N1—C6—C5 | 121.66 (17) | C27—C31—H31 | 126.0 |
C1—C6—C5 | 119.84 (17) | Fe1—C31—H31 | 126.5 |
N1—C7—C8 | 123.88 (15) | C33—C32—C36 | 107.2 (3) |
N1—C7—C11 | 125.63 (15) | C33—C32—Fe1 | 70.14 (13) |
C8—C7—C11 | 110.48 (15) | C36—C32—Fe1 | 69.44 (15) |
N2—C8—C7 | 123.60 (18) | C33—C32—H32 | 126.4 |
N2—C8—C9 | 127.79 (17) | C36—C32—H32 | 126.4 |
C7—C8—C9 | 108.56 (15) | Fe1—C32—H32 | 125.6 |
C15—C9—C10 | 121.06 (19) | C34—C33—C32 | 107.9 (2) |
C15—C9—C8 | 130.39 (19) | C34—C33—Fe1 | 70.17 (13) |
C10—C9—C8 | 108.48 (15) | C32—C33—Fe1 | 69.59 (13) |
C12—C10—C9 | 119.76 (17) | C34—C33—H33 | 126.0 |
C12—C10—C11 | 128.28 (16) | C32—C33—H33 | 126.0 |
C9—C10—C11 | 111.88 (15) | Fe1—C33—H33 | 125.8 |
N3—C11—C10 | 110.80 (12) | C33—C34—C35 | 108.7 (3) |
N3—C11—C7 | 116.62 (13) | C33—C34—Fe1 | 70.45 (13) |
C10—C11—C7 | 100.53 (13) | C35—C34—Fe1 | 69.48 (14) |
N3—C11—C16 | 102.27 (12) | C33—C34—H34 | 125.6 |
C10—C11—C16 | 117.61 (13) | C35—C34—H34 | 125.6 |
C7—C11—C16 | 109.73 (12) | Fe1—C34—H34 | 126.0 |
C10—C12—C13 | 118.9 (2) | C34—C35—C36 | 108.3 (3) |
C10—C12—H12 | 120.6 | C34—C35—Fe1 | 70.82 (15) |
C13—C12—H12 | 120.6 | C36—C35—Fe1 | 70.11 (14) |
C14—C13—C12 | 121.1 (2) | C34—C35—H35 | 125.8 |
C14—C13—H13 | 119.5 | C36—C35—H35 | 125.8 |
C12—C13—H13 | 119.5 | Fe1—C35—H35 | 124.8 |
C15—C14—C13 | 120.8 (2) | C35—C36—C32 | 107.8 (3) |
C15—C14—H14 | 119.6 | C35—C36—Fe1 | 69.84 (16) |
C13—C14—H14 | 119.6 | C32—C36—Fe1 | 70.21 (14) |
C14—C15—C9 | 118.4 (2) | C35—C36—H36 | 126.1 |
C14—C15—H15 | 120.8 | C32—C36—H36 | 126.1 |
C9—C15—H15 | 120.8 | Fe1—C36—H36 | 125.4 |
C26—C16—C17 | 114.62 (12) | C23—C37—H37A | 109.5 |
C26—C16—C11 | 111.53 (12) | C23—C37—H37B | 109.5 |
C17—C16—C11 | 105.82 (12) | H37A—C37—H37B | 109.5 |
C26—C16—H16 | 108.2 | C23—C37—H37C | 109.5 |
C17—C16—H16 | 108.2 | H37A—C37—H37C | 109.5 |
C11—C16—H16 | 108.2 | H37B—C37—H37C | 109.5 |
C18—C17—C20 | 114.90 (14) | C7—N1—C6 | 114.35 (15) |
C18—C17—C16 | 103.84 (12) | C8—N2—C5 | 114.00 (17) |
C20—C17—C16 | 112.60 (13) | C19—N3—C18 | 115.01 (14) |
C18—C17—H17 | 108.4 | C19—N3—C11 | 116.54 (13) |
C20—C17—H17 | 108.4 | C18—N3—C11 | 107.65 (12) |
C16—C17—H17 | 108.4 | C35—Fe1—C27 | 158.95 (12) |
N3—C18—C17 | 103.35 (13) | C35—Fe1—C36 | 40.05 (13) |
N3—C18—H18A | 111.1 | C27—Fe1—C36 | 123.19 (11) |
C17—C18—H18A | 111.1 | C35—Fe1—C32 | 67.39 (13) |
N3—C18—H18B | 111.1 | C27—Fe1—C32 | 108.14 (9) |
C17—C18—H18B | 111.1 | C36—Fe1—C32 | 40.35 (12) |
H18A—C18—H18B | 109.1 | C35—Fe1—C34 | 39.71 (12) |
N3—C19—H19A | 109.5 | C27—Fe1—C34 | 159.51 (11) |
N3—C19—H19B | 109.5 | C36—Fe1—C34 | 66.96 (12) |
H19A—C19—H19B | 109.5 | C32—Fe1—C34 | 66.95 (11) |
N3—C19—H19C | 109.5 | C35—Fe1—C28 | 122.02 (11) |
H19A—C19—H19C | 109.5 | C27—Fe1—C28 | 41.22 (6) |
H19B—C19—H19C | 109.5 | C36—Fe1—C28 | 105.92 (10) |
C21—C20—C25 | 117.41 (16) | C32—Fe1—C28 | 121.56 (9) |
C21—C20—C17 | 121.82 (15) | C34—Fe1—C28 | 158.70 (11) |
C25—C20—C17 | 120.75 (15) | C35—Fe1—C33 | 66.84 (11) |
C20—C21—C22 | 121.10 (18) | C27—Fe1—C33 | 124.02 (9) |
C20—C21—H21 | 119.5 | C36—Fe1—C33 | 67.40 (11) |
C22—C21—H21 | 119.5 | C32—Fe1—C33 | 40.27 (10) |
C23—C22—C21 | 121.60 (18) | C34—Fe1—C33 | 39.38 (11) |
C23—C22—H22 | 119.2 | C28—Fe1—C33 | 158.62 (10) |
C21—C22—H22 | 119.2 | C35—Fe1—C31 | 157.57 (13) |
C22—C23—C24 | 117.38 (17) | C27—Fe1—C31 | 41.54 (6) |
C22—C23—C37 | 122.12 (18) | C36—Fe1—C31 | 161.66 (13) |
C24—C23—C37 | 120.50 (19) | C32—Fe1—C31 | 126.18 (10) |
C23—C24—C25 | 121.52 (18) | C34—Fe1—C31 | 123.94 (11) |
C23—C24—H24 | 119.2 | C28—Fe1—C31 | 69.01 (7) |
C25—C24—H24 | 119.2 | C33—Fe1—C31 | 110.55 (9) |
C24—C25—C20 | 120.98 (17) | C35—Fe1—C29 | 106.73 (11) |
C24—C25—H25 | 119.5 | C27—Fe1—C29 | 68.61 (7) |
C20—C25—H25 | 119.5 | C36—Fe1—C29 | 120.34 (11) |
O1—C26—C27 | 121.96 (15) | C32—Fe1—C29 | 156.28 (11) |
O1—C26—C16 | 121.68 (14) | C34—Fe1—C29 | 124.16 (10) |
C27—C26—C16 | 116.33 (13) | C28—Fe1—C29 | 40.44 (7) |
C28—C27—C31 | 107.21 (14) | C33—Fe1—C29 | 160.65 (10) |
C28—C27—C26 | 125.44 (14) | C31—Fe1—C29 | 67.96 (7) |
C31—C27—C26 | 126.87 (14) | C35—Fe1—C30 | 121.88 (13) |
C28—C27—Fe1 | 69.92 (9) | C27—Fe1—C30 | 68.69 (7) |
C31—C27—Fe1 | 69.94 (9) | C36—Fe1—C30 | 156.05 (13) |
C26—C27—Fe1 | 119.20 (10) | C32—Fe1—C30 | 162.39 (11) |
C29—C28—C27 | 107.88 (16) | C34—Fe1—C30 | 109.57 (10) |
C29—C28—Fe1 | 70.51 (10) | C28—Fe1—C30 | 68.26 (8) |
C27—C28—Fe1 | 68.86 (9) | C33—Fe1—C30 | 126.09 (10) |
C29—C28—H28 | 126.1 | C31—Fe1—C30 | 40.09 (7) |
C27—C28—H28 | 126.1 | C29—Fe1—C30 | 40.29 (8) |
Fe1—C28—H28 | 126.1 | ||
C6—C1—C2—C3 | 0.3 (3) | C26—C27—Fe1—C36 | −44.61 (18) |
C1—C2—C3—C4 | 1.8 (3) | C28—C27—Fe1—C32 | 117.50 (13) |
C2—C3—C4—C5 | −2.0 (3) | C31—C27—Fe1—C32 | −124.53 (13) |
C3—C4—C5—N2 | −177.95 (19) | C26—C27—Fe1—C32 | −2.69 (16) |
C3—C4—C5—C6 | 0.1 (3) | C28—C27—Fe1—C34 | −170.0 (3) |
C2—C1—C6—N1 | 177.18 (17) | C31—C27—Fe1—C34 | −52.0 (3) |
C2—C1—C6—C5 | −2.2 (3) | C26—C27—Fe1—C34 | 69.9 (3) |
N2—C5—C6—N1 | 0.6 (3) | C31—C27—Fe1—C28 | 117.96 (14) |
C4—C5—C6—N1 | −177.38 (16) | C26—C27—Fe1—C28 | −120.19 (16) |
N2—C5—C6—C1 | 179.95 (16) | C28—C27—Fe1—C33 | 159.12 (12) |
C4—C5—C6—C1 | 2.0 (3) | C31—C27—Fe1—C33 | −82.91 (13) |
N1—C7—C8—N2 | 1.3 (3) | C26—C27—Fe1—C33 | 38.93 (16) |
C11—C7—C8—N2 | −179.79 (15) | C28—C27—Fe1—C31 | −117.96 (14) |
N1—C7—C8—C9 | 178.99 (15) | C26—C27—Fe1—C31 | 121.85 (16) |
C11—C7—C8—C9 | −2.10 (18) | C28—C27—Fe1—C29 | −37.51 (11) |
N2—C8—C9—C15 | 1.2 (3) | C31—C27—Fe1—C29 | 80.46 (11) |
C7—C8—C9—C15 | −176.42 (19) | C26—C27—Fe1—C29 | −157.70 (14) |
N2—C8—C9—C10 | 178.05 (17) | C28—C27—Fe1—C30 | −80.91 (11) |
C7—C8—C9—C10 | 0.48 (19) | C31—C27—Fe1—C30 | 37.05 (10) |
C15—C9—C10—C12 | 1.7 (3) | C26—C27—Fe1—C30 | 158.90 (14) |
C8—C9—C10—C12 | −175.58 (16) | C32—C36—Fe1—C35 | −118.5 (2) |
C15—C9—C10—C11 | 178.59 (16) | C35—C36—Fe1—C27 | −162.74 (16) |
C8—C9—C10—C11 | 1.34 (19) | C32—C36—Fe1—C27 | 78.74 (17) |
C12—C10—C11—N3 | 50.2 (2) | C35—C36—Fe1—C32 | 118.5 (2) |
C9—C10—C11—N3 | −126.35 (15) | C35—C36—Fe1—C34 | 37.51 (18) |
C12—C10—C11—C7 | 174.18 (17) | C32—C36—Fe1—C34 | −81.01 (18) |
C9—C10—C11—C7 | −2.42 (17) | C35—C36—Fe1—C28 | −121.17 (17) |
C12—C10—C11—C16 | −66.8 (2) | C32—C36—Fe1—C28 | 120.32 (16) |
C9—C10—C11—C16 | 116.57 (16) | C35—C36—Fe1—C33 | 80.39 (19) |
N1—C7—C11—N3 | −58.6 (2) | C32—C36—Fe1—C33 | −38.13 (16) |
C8—C7—C11—N3 | 122.49 (15) | C35—C36—Fe1—C31 | 167.7 (2) |
N1—C7—C11—C10 | −178.43 (15) | C32—C36—Fe1—C31 | 49.2 (4) |
C8—C7—C11—C10 | 2.68 (16) | C35—C36—Fe1—C29 | −79.76 (19) |
N1—C7—C11—C16 | 57.0 (2) | C32—C36—Fe1—C29 | 161.73 (14) |
C8—C7—C11—C16 | −121.89 (14) | C35—C36—Fe1—C30 | −49.0 (3) |
C9—C10—C12—C13 | −2.1 (3) | C32—C36—Fe1—C30 | −167.52 (19) |
C11—C10—C12—C13 | −178.46 (18) | C33—C32—Fe1—C35 | −80.36 (18) |
C10—C12—C13—C14 | 1.2 (3) | C36—C32—Fe1—C35 | 37.77 (17) |
C12—C13—C14—C15 | 0.2 (4) | C33—C32—Fe1—C27 | 121.61 (15) |
C13—C14—C15—C9 | −0.7 (3) | C36—C32—Fe1—C27 | −120.26 (17) |
C10—C9—C15—C14 | −0.2 (3) | C33—C32—Fe1—C36 | −118.1 (2) |
C8—C9—C15—C14 | 176.3 (2) | C33—C32—Fe1—C34 | −37.11 (16) |
N3—C11—C16—C26 | −112.15 (13) | C36—C32—Fe1—C34 | 81.01 (19) |
C10—C11—C16—C26 | 9.44 (19) | C33—C32—Fe1—C28 | 164.92 (14) |
C7—C11—C16—C26 | 123.43 (14) | C36—C32—Fe1—C28 | −76.96 (19) |
N3—C11—C16—C17 | 13.11 (15) | C36—C32—Fe1—C33 | 118.1 (2) |
C10—C11—C16—C17 | 134.70 (14) | C33—C32—Fe1—C31 | 79.02 (17) |
C7—C11—C16—C17 | −111.31 (14) | C36—C32—Fe1—C31 | −162.85 (16) |
C26—C16—C17—C18 | 134.85 (13) | C33—C32—Fe1—C29 | −160.4 (2) |
C11—C16—C17—C18 | 11.52 (15) | C36—C32—Fe1—C29 | −42.3 (3) |
C26—C16—C17—C20 | −100.24 (15) | C33—C32—Fe1—C30 | 45.0 (4) |
C11—C16—C17—C20 | 136.43 (13) | C36—C32—Fe1—C30 | 163.1 (3) |
C20—C17—C18—N3 | −155.76 (13) | C33—C34—Fe1—C35 | 119.8 (3) |
C16—C17—C18—N3 | −32.34 (16) | C33—C34—Fe1—C27 | −42.2 (4) |
C18—C17—C20—C21 | −125.50 (18) | C35—C34—Fe1—C27 | −162.0 (3) |
C16—C17—C20—C21 | 115.89 (18) | C33—C34—Fe1—C36 | 82.0 (2) |
C18—C17—C20—C25 | 55.8 (2) | C35—C34—Fe1—C36 | −37.8 (2) |
C16—C17—C20—C25 | −62.8 (2) | C33—C34—Fe1—C32 | 37.94 (17) |
C25—C20—C21—C22 | 1.3 (3) | C35—C34—Fe1—C32 | −81.8 (2) |
C17—C20—C21—C22 | −177.46 (18) | C33—C34—Fe1—C28 | 156.3 (2) |
C20—C21—C22—C23 | −1.6 (3) | C35—C34—Fe1—C28 | 36.5 (4) |
C21—C22—C23—C24 | 0.9 (3) | C35—C34—Fe1—C33 | −119.8 (3) |
C21—C22—C23—C37 | −178.43 (19) | C33—C34—Fe1—C31 | −81.20 (18) |
C22—C23—C24—C25 | −0.1 (3) | C35—C34—Fe1—C31 | 159.02 (19) |
C37—C23—C24—C25 | 179.34 (18) | C33—C34—Fe1—C29 | −166.04 (14) |
C23—C24—C25—C20 | −0.2 (3) | C35—C34—Fe1—C29 | 74.2 (2) |
C21—C20—C25—C24 | −0.4 (3) | C33—C34—Fe1—C30 | −123.52 (16) |
C17—C20—C25—C24 | 178.36 (16) | C35—C34—Fe1—C30 | 116.7 (2) |
C17—C16—C26—O1 | −26.9 (2) | C29—C28—Fe1—C35 | 77.86 (18) |
C11—C16—C26—O1 | 93.32 (17) | C27—C28—Fe1—C35 | −163.05 (16) |
C17—C16—C26—C27 | 154.99 (13) | C29—C28—Fe1—C27 | −119.08 (15) |
C11—C16—C26—C27 | −84.80 (15) | C29—C28—Fe1—C36 | 118.36 (16) |
O1—C26—C27—C28 | 1.6 (2) | C27—C28—Fe1—C36 | −122.55 (15) |
C16—C26—C27—C28 | 179.68 (14) | C29—C28—Fe1—C32 | 159.35 (14) |
O1—C26—C27—C31 | 172.55 (16) | C27—C28—Fe1—C32 | −81.57 (15) |
C16—C26—C27—C31 | −9.3 (2) | C29—C28—Fe1—C34 | 51.2 (3) |
O1—C26—C27—Fe1 | 86.68 (17) | C27—C28—Fe1—C34 | 170.3 (3) |
C16—C26—C27—Fe1 | −95.21 (14) | C29—C28—Fe1—C33 | −173.2 (2) |
C31—C27—C28—C29 | −0.34 (19) | C27—C28—Fe1—C33 | −54.1 (3) |
C26—C27—C28—C29 | 172.13 (15) | C29—C28—Fe1—C31 | −80.23 (12) |
Fe1—C27—C28—C29 | 59.96 (13) | C27—C28—Fe1—C31 | 38.85 (10) |
C31—C27—C28—Fe1 | −60.29 (11) | C27—C28—Fe1—C29 | 119.08 (15) |
C26—C27—C28—Fe1 | 112.17 (15) | C29—C28—Fe1—C30 | −37.05 (11) |
C27—C28—C29—C30 | 0.0 (2) | C27—C28—Fe1—C30 | 82.03 (11) |
Fe1—C28—C29—C30 | 58.96 (14) | C34—C33—Fe1—C35 | −37.09 (19) |
C27—C28—C29—Fe1 | −58.93 (12) | C32—C33—Fe1—C35 | 81.8 (2) |
C28—C29—C30—C31 | 0.3 (2) | C34—C33—Fe1—C27 | 163.53 (16) |
Fe1—C29—C30—C31 | 58.72 (13) | C32—C33—Fe1—C27 | −77.54 (17) |
C28—C29—C30—Fe1 | −58.43 (13) | C34—C33—Fe1—C36 | −80.7 (2) |
C29—C30—C31—C27 | −0.5 (2) | C32—C33—Fe1—C36 | 38.20 (18) |
Fe1—C30—C31—C27 | 58.50 (11) | C34—C33—Fe1—C32 | −118.9 (2) |
C29—C30—C31—Fe1 | −59.00 (14) | C32—C33—Fe1—C34 | 118.9 (2) |
C28—C27—C31—C30 | 0.51 (19) | C34—C33—Fe1—C28 | −156.4 (2) |
C26—C27—C31—C30 | −171.81 (15) | C32—C33—Fe1—C28 | −37.4 (3) |
Fe1—C27—C31—C30 | −59.76 (12) | C34—C33—Fe1—C31 | 118.88 (17) |
C28—C27—C31—Fe1 | 60.28 (11) | C32—C33—Fe1—C31 | −122.19 (16) |
C26—C27—C31—Fe1 | −112.05 (15) | C34—C33—Fe1—C29 | 37.1 (4) |
C36—C32—C33—C34 | 0.1 (3) | C32—C33—Fe1—C29 | 156.0 (3) |
Fe1—C32—C33—C34 | 59.93 (17) | C34—C33—Fe1—C30 | 76.43 (19) |
C36—C32—C33—Fe1 | −59.82 (16) | C32—C33—Fe1—C30 | −164.64 (15) |
C32—C33—C34—C35 | −0.4 (3) | C30—C31—Fe1—C35 | −43.2 (3) |
Fe1—C33—C34—C35 | 59.12 (18) | C27—C31—Fe1—C35 | −162.6 (2) |
C32—C33—C34—Fe1 | −59.57 (15) | C30—C31—Fe1—C27 | 119.34 (15) |
C33—C34—C35—C36 | 0.6 (3) | C30—C31—Fe1—C36 | 157.9 (3) |
Fe1—C34—C35—C36 | 60.33 (18) | C27—C31—Fe1—C36 | 38.5 (3) |
C33—C34—C35—Fe1 | −59.72 (18) | C30—C31—Fe1—C32 | −164.77 (13) |
C34—C35—C36—C32 | −0.5 (3) | C27—C31—Fe1—C32 | 75.89 (13) |
Fe1—C35—C36—C32 | 60.25 (17) | C30—C31—Fe1—C34 | −80.07 (15) |
C34—C35—C36—Fe1 | −60.78 (19) | C27—C31—Fe1—C34 | 160.58 (13) |
C33—C32—C36—C35 | 0.3 (3) | C30—C31—Fe1—C28 | 80.78 (12) |
Fe1—C32—C36—C35 | −60.01 (18) | C27—C31—Fe1—C28 | −38.56 (9) |
C33—C32—C36—Fe1 | 60.27 (15) | C30—C31—Fe1—C33 | −122.11 (13) |
C8—C7—N1—C6 | −2.9 (2) | C27—C31—Fe1—C33 | 118.55 (12) |
C11—C7—N1—C6 | 178.34 (14) | C30—C31—Fe1—C29 | 37.17 (11) |
C1—C6—N1—C7 | −177.38 (15) | C27—C31—Fe1—C29 | −82.17 (11) |
C5—C6—N1—C7 | 2.0 (2) | C27—C31—Fe1—C30 | −119.34 (15) |
C7—C8—N2—C5 | 1.4 (2) | C30—C29—Fe1—C35 | 119.88 (16) |
C9—C8—N2—C5 | −175.84 (16) | C28—C29—Fe1—C35 | −120.06 (16) |
C6—C5—N2—C8 | −2.2 (2) | C30—C29—Fe1—C27 | −81.86 (12) |
C4—C5—N2—C8 | 175.73 (17) | C28—C29—Fe1—C27 | 38.20 (10) |
C17—C18—N3—C19 | 175.16 (14) | C30—C29—Fe1—C36 | 161.28 (16) |
C17—C18—N3—C11 | 43.41 (16) | C28—C29—Fe1—C36 | −78.66 (17) |
C10—C11—N3—C19 | 68.04 (18) | C30—C29—Fe1—C32 | −168.4 (2) |
C7—C11—N3—C19 | −46.10 (19) | C28—C29—Fe1—C32 | −48.4 (3) |
C16—C11—N3—C19 | −165.80 (14) | C30—C29—Fe1—C34 | 79.95 (16) |
C10—C11—N3—C18 | −161.05 (13) | C28—C29—Fe1—C34 | −159.99 (14) |
C7—C11—N3—C18 | 84.81 (16) | C30—C29—Fe1—C28 | −120.06 (16) |
C16—C11—N3—C18 | −34.89 (15) | C30—C29—Fe1—C33 | 52.4 (3) |
C34—C35—Fe1—C27 | 162.4 (2) | C28—C29—Fe1—C33 | 172.5 (2) |
C36—C35—Fe1—C27 | 43.7 (4) | C30—C29—Fe1—C31 | −36.99 (11) |
C34—C35—Fe1—C36 | 118.7 (3) | C28—C29—Fe1—C31 | 83.07 (11) |
C34—C35—Fe1—C32 | 80.7 (2) | C28—C29—Fe1—C30 | 120.06 (16) |
C36—C35—Fe1—C32 | −38.04 (17) | C31—C30—Fe1—C35 | 162.08 (14) |
C36—C35—Fe1—C34 | −118.7 (3) | C29—C30—Fe1—C35 | −77.92 (17) |
C34—C35—Fe1—C28 | −165.24 (16) | C31—C30—Fe1—C27 | −38.35 (10) |
C36—C35—Fe1—C28 | 76.0 (2) | C29—C30—Fe1—C27 | 81.65 (12) |
C34—C35—Fe1—C33 | 36.79 (18) | C31—C30—Fe1—C36 | −163.0 (2) |
C36—C35—Fe1—C33 | −81.92 (19) | C29—C30—Fe1—C36 | −43.0 (3) |
C34—C35—Fe1—C31 | −51.2 (4) | C31—C30—Fe1—C32 | 44.5 (3) |
C36—C35—Fe1—C31 | −169.9 (2) | C29—C30—Fe1—C32 | 164.5 (3) |
C34—C35—Fe1—C29 | −123.77 (19) | C31—C30—Fe1—C34 | 119.85 (14) |
C36—C35—Fe1—C29 | 117.52 (18) | C29—C30—Fe1—C34 | −120.15 (14) |
C34—C35—Fe1—C30 | −82.4 (2) | C31—C30—Fe1—C28 | −82.81 (11) |
C36—C35—Fe1—C30 | 158.85 (17) | C29—C30—Fe1—C28 | 37.19 (11) |
C28—C27—Fe1—C35 | 43.5 (3) | C31—C30—Fe1—C33 | 78.96 (15) |
C31—C27—Fe1—C35 | 161.4 (3) | C29—C30—Fe1—C33 | −161.03 (13) |
C26—C27—Fe1—C35 | −76.7 (3) | C29—C30—Fe1—C31 | 120.00 (16) |
C28—C27—Fe1—C36 | 75.58 (16) | C31—C30—Fe1—C29 | −120.00 (16) |
C31—C27—Fe1—C36 | −166.46 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28···N3i | 0.93 | 2.49 | 3.416 (2) | 176 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C32H26N3O)] |
Mr | 589.50 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.5966 (3), 11.8658 (3), 20.9383 (6) |
β (°) | 90.616 (2) |
V (Å3) | 2881.01 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.56 |
Crystal size (mm) | 0.2 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26509, 7145, 5247 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.110, 1.02 |
No. of reflections | 7145 |
No. of parameters | 381 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.31 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28···N3i | 0.93 | 2.49 | 3.416 (2) | 176 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. BV thanks the University Grant Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship.
References
Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678–4682. Web of Science CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fouda, 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
Gunasekaran, B., Kathiravan, S., Raghunathan, R. & Manivannan, V. (2010). Acta Cryst. E66, m1543. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jaouen, 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
Kamala, 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
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2007). Acta Cryst. E63, m1287–m1289. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Ferrocene attached compounds have prominent biological activities like antitumor (Jaouen et al., 2004), antimalarial and antifungal (Biot et al., 2004), and antibacterial (Fouda et al., 2007) and find applications in medicinal chemistry. In this background, X-ray study of the title compound was carried out to obtain the information of molecular conformations and crystal packing in the solid state.
X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles of titled compound agree with those observed in other ferrocene derivative 4'-Ferrocenyl-3'- 4-methoxybenzoyl)-1'-methylspiro[1H-indole-3(2H), 2'-pyrrolidin]-2-one (Satis Kumar et al., 2007). The dihedral angle between indeno-quinoxaline ring system and the pyrrolidine ring is 87.84 (7)° and the dihedral angle between pyrrolidine ring and the phenyl ring is 86.06 (9) °. The dihedral angle between pyrrolidine ring and the ferrocene rings are 81.00 (10)° and 83.94 (12)°. This clearly shows that the indeno-quinoxaline ring system, the phenyl and ferrocene rings are almost perpendicular to the pyrrolidine ring.
The pyrrolidine ring adopts a twisted conformation with the puckering parameters q2 and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, δ, (Nardelli, 1983) as follows: q2 = 0.3858 (16) Å, φ = 343.1 (3)° and Δ2 (C16) = 2.13 (15)°. In the ferrocene, Cg3 and Cg4 are the centroids of the C27—C31 and C32—C36 rings, respectively. Fe1—Cg3 and Fe1—Cg4 distances are 1.6430 (8) and 1.6495 (10) Å, respectively and the Cg3—Fe1—Cg4 angle is 177.74 (6)°. In addition to the van der Waals interactions, the crystal packing is stabilized by C—H···N interaction (Table. 1 & Fig. 2).