metal-organic compounds
4-Ferrocenyl-1-methyl-3-benzoylspiro[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)(C31H24N3O)], the pyrrolidine ring adopts a twist conformation. The pyrrolidine ring is almost perpendicular to the indenoquinoxaline ring system, making a dihedral angle of 84.44 (5)°. The cyclopentadienyl rings of the ferrocene moiety adopt an eclipsed conformation. The crystal packing features weak C—H⋯N and C—H⋯π 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: Kamala et al. (2009); Gunasekaran et al. (2010); Vijayakumar et al. (2012); For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).
Experimental
Crystal data
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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, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812048349/bt6861sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048349/bt6861Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812048349/bt6861Isup3.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 a fixed isotropic displacement parameter of Uiso(H) = 1.2 Ueq(C).
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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).[Fe(C5H5)(C31H24N3O)] | Z = 4 |
Mr = 575.47 | F(000) = 1200 |
Monoclinic, P21/c | Dx = 1.391 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8091 (18) Å | θ = 2.0–28.3° |
b = 12.326 (2) Å | µ = 0.58 mm−1 |
c = 20.989 (3) Å | T = 293 K |
β = 100.654 (8)° | Block, brown |
V = 2748.2 (8) Å3 | 0.2 × 0.2 × 0.2 mm |
Bruker SMART APEXII area-detector diffractometer | 6927 independent reflections |
Radiation source: fine-focus sealed tube | 5624 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and ϕ scans | θmax = 28.6°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −14→14 |
Tmin = 0.890, Tmax = 0.890 | k = −16→14 |
27206 measured reflections | l = −28→27 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0582P)2 + 0.6864P] where P = (Fo2 + 2Fc2)/3 |
6927 reflections | (Δ/σ)max = 0.002 |
371 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
[Fe(C5H5)(C31H24N3O)] | V = 2748.2 (8) Å3 |
Mr = 575.47 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.8091 (18) Å | µ = 0.58 mm−1 |
b = 12.326 (2) Å | T = 293 K |
c = 20.989 (3) Å | 0.2 × 0.2 × 0.2 mm |
β = 100.654 (8)° |
Bruker SMART APEXII area-detector diffractometer | 6927 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 5624 reflections with I > 2σ(I) |
Tmin = 0.890, Tmax = 0.890 | Rint = 0.028 |
27206 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.30 e Å−3 |
6927 reflections | Δρmin = −0.44 e Å−3 |
371 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 | 0.79681 (14) | 0.51846 (13) | 0.70367 (8) | 0.0417 (3) | |
H1 | 0.8397 | 0.5059 | 0.7457 | 0.050* | |
C2 | 0.80655 (16) | 0.61717 (14) | 0.67526 (9) | 0.0480 (4) | |
H2 | 0.8561 | 0.6713 | 0.6980 | 0.058* | |
C3 | 0.74260 (17) | 0.63721 (15) | 0.61233 (9) | 0.0513 (4) | |
H3 | 0.7494 | 0.7048 | 0.5936 | 0.062* | |
C4 | 0.67032 (16) | 0.55878 (14) | 0.57805 (9) | 0.0475 (4) | |
H4 | 0.6284 | 0.5733 | 0.5361 | 0.057* | |
C5 | 0.65853 (13) | 0.45581 (12) | 0.60556 (7) | 0.0351 (3) | |
C6 | 0.72248 (13) | 0.43585 (12) | 0.66985 (7) | 0.0332 (3) | |
C7 | 0.63802 (12) | 0.26813 (11) | 0.66576 (6) | 0.0314 (3) | |
C8 | 0.57653 (13) | 0.28695 (12) | 0.60063 (6) | 0.0323 (3) | |
C9 | 0.50426 (13) | 0.19007 (12) | 0.57774 (7) | 0.0345 (3) | |
C10 | 0.52049 (13) | 0.11230 (12) | 0.62698 (7) | 0.0339 (3) | |
C11 | 0.60275 (13) | 0.15690 (11) | 0.68865 (6) | 0.0314 (3) | |
C12 | 0.45706 (15) | 0.01405 (13) | 0.61673 (8) | 0.0422 (3) | |
H12 | 0.4672 | −0.0388 | 0.6489 | 0.051* | |
C13 | 0.37828 (15) | −0.00376 (14) | 0.55751 (8) | 0.0459 (4) | |
H13 | 0.3344 | −0.0688 | 0.5504 | 0.055* | |
C14 | 0.36392 (15) | 0.07330 (15) | 0.50904 (8) | 0.0469 (4) | |
H14 | 0.3112 | 0.0593 | 0.4696 | 0.056* | |
C15 | 0.42706 (15) | 0.17096 (14) | 0.51848 (7) | 0.0424 (3) | |
H15 | 0.4179 | 0.2228 | 0.4857 | 0.051* | |
C16 | 0.71773 (12) | 0.08849 (11) | 0.72140 (6) | 0.0306 (3) | |
H16 | 0.7793 | 0.1376 | 0.7466 | 0.037* | |
C17 | 0.66473 (13) | 0.01436 (12) | 0.76915 (7) | 0.0334 (3) | |
H17 | 0.6455 | −0.0563 | 0.7483 | 0.040* | |
C18 | 0.53991 (14) | 0.06744 (14) | 0.77724 (8) | 0.0414 (3) | |
H18A | 0.4690 | 0.0226 | 0.7580 | 0.050* | |
H18B | 0.5373 | 0.0783 | 0.8227 | 0.050* | |
C19 | 0.41254 (17) | 0.22002 (16) | 0.72858 (9) | 0.0522 (4) | |
H19A | 0.3545 | 0.1694 | 0.7045 | 0.078* | |
H19B | 0.4159 | 0.2844 | 0.7032 | 0.078* | |
H19C | 0.3850 | 0.2386 | 0.7681 | 0.078* | |
C20 | 0.75808 (14) | −0.00309 (11) | 0.83087 (7) | 0.0340 (3) | |
C21 | 0.73116 (17) | −0.03810 (13) | 0.89135 (7) | 0.0433 (4) | |
H21 | 0.6516 | −0.0514 | 0.9005 | 0.052* | |
C22 | 0.84766 (19) | −0.04913 (14) | 0.93543 (8) | 0.0506 (4) | |
H22 | 0.8571 | −0.0704 | 0.9786 | 0.061* | |
C23 | 0.94568 (17) | −0.02255 (14) | 0.90278 (8) | 0.0499 (4) | |
H23 | 1.0312 | −0.0233 | 0.9204 | 0.060* | |
C24 | 0.89125 (15) | 0.00566 (13) | 0.83792 (8) | 0.0404 (3) | |
H24 | 0.9351 | 0.0262 | 0.8057 | 0.048* | |
C25 | 0.7390 (2) | 0.25002 (16) | 0.87637 (10) | 0.0648 (6) | |
H25 | 0.6786 | 0.2628 | 0.8394 | 0.078* | |
C26 | 0.7154 (2) | 0.21523 (17) | 0.93713 (11) | 0.0692 (6) | |
H26 | 0.6371 | 0.2004 | 0.9474 | 0.083* | |
C27 | 0.8317 (3) | 0.20723 (18) | 0.97903 (10) | 0.0738 (7) | |
H27 | 0.8439 | 0.1866 | 1.0223 | 0.089* | |
C28 | 0.9260 (3) | 0.23524 (18) | 0.94526 (13) | 0.0755 (7) | |
H28 | 1.0119 | 0.2362 | 0.9619 | 0.091* | |
C29 | 0.8690 (3) | 0.26178 (16) | 0.88154 (12) | 0.0723 (6) | |
H29 | 0.9105 | 0.2834 | 0.8486 | 0.087* | |
C30 | 0.78362 (13) | 0.02473 (12) | 0.67524 (7) | 0.0352 (3) | |
C31 | 0.89465 (13) | 0.07269 (13) | 0.65201 (7) | 0.0359 (3) | |
C32 | 0.95018 (16) | 0.01150 (17) | 0.60885 (9) | 0.0523 (4) | |
H32 | 0.9162 | −0.0554 | 0.5946 | 0.063* | |
C33 | 1.05538 (18) | 0.0497 (2) | 0.58717 (10) | 0.0638 (5) | |
H33 | 1.0920 | 0.0082 | 0.5586 | 0.077* | |
C34 | 1.10601 (17) | 0.14888 (19) | 0.60772 (10) | 0.0590 (5) | |
H34 | 1.1764 | 0.1744 | 0.5928 | 0.071* | |
C35 | 1.05280 (17) | 0.21050 (15) | 0.65028 (10) | 0.0525 (4) | |
H35 | 1.0875 | 0.2774 | 0.6642 | 0.063* | |
C36 | 0.94712 (15) | 0.17263 (13) | 0.67245 (8) | 0.0423 (3) | |
H36 | 0.9113 | 0.2145 | 0.7011 | 0.051* | |
N1 | 0.71034 (11) | 0.33856 (10) | 0.70041 (6) | 0.0347 (3) | |
N2 | 0.58371 (12) | 0.37874 (10) | 0.57026 (6) | 0.0375 (3) | |
N3 | 0.53706 (11) | 0.17117 (11) | 0.74359 (6) | 0.0367 (3) | |
O1 | 0.74771 (12) | −0.06575 (10) | 0.65798 (6) | 0.0535 (3) | |
Fe1 | 0.82624 (2) | 0.106179 (18) | 0.901638 (10) | 0.04051 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0384 (8) | 0.0414 (9) | 0.0436 (8) | −0.0029 (6) | 0.0034 (6) | 0.0010 (7) |
C2 | 0.0429 (8) | 0.0394 (9) | 0.0605 (10) | −0.0091 (7) | 0.0063 (7) | −0.0014 (7) |
C3 | 0.0542 (10) | 0.0364 (8) | 0.0620 (11) | −0.0066 (7) | 0.0072 (8) | 0.0125 (8) |
C4 | 0.0540 (9) | 0.0402 (9) | 0.0468 (9) | −0.0024 (7) | 0.0050 (7) | 0.0129 (7) |
C5 | 0.0361 (7) | 0.0335 (7) | 0.0362 (7) | 0.0010 (6) | 0.0080 (5) | 0.0042 (6) |
C6 | 0.0311 (6) | 0.0316 (7) | 0.0378 (7) | 0.0020 (5) | 0.0087 (5) | 0.0024 (6) |
C7 | 0.0326 (6) | 0.0308 (7) | 0.0308 (6) | 0.0025 (5) | 0.0056 (5) | 0.0039 (5) |
C8 | 0.0331 (6) | 0.0331 (7) | 0.0303 (6) | 0.0026 (5) | 0.0051 (5) | 0.0030 (5) |
C9 | 0.0340 (7) | 0.0351 (7) | 0.0335 (7) | 0.0011 (6) | 0.0033 (5) | 0.0011 (6) |
C10 | 0.0325 (6) | 0.0336 (7) | 0.0346 (7) | 0.0001 (5) | 0.0034 (5) | 0.0013 (5) |
C11 | 0.0329 (6) | 0.0303 (7) | 0.0304 (6) | 0.0001 (5) | 0.0041 (5) | 0.0044 (5) |
C12 | 0.0428 (8) | 0.0370 (8) | 0.0453 (8) | −0.0047 (6) | 0.0043 (6) | 0.0039 (6) |
C13 | 0.0417 (8) | 0.0406 (9) | 0.0533 (9) | −0.0076 (7) | 0.0032 (7) | −0.0079 (7) |
C14 | 0.0421 (8) | 0.0514 (10) | 0.0431 (8) | −0.0023 (7) | −0.0025 (6) | −0.0073 (7) |
C15 | 0.0453 (8) | 0.0433 (9) | 0.0351 (7) | 0.0004 (7) | −0.0018 (6) | 0.0022 (6) |
C16 | 0.0309 (6) | 0.0296 (7) | 0.0305 (6) | −0.0013 (5) | 0.0037 (5) | 0.0047 (5) |
C17 | 0.0368 (7) | 0.0309 (7) | 0.0317 (6) | −0.0032 (5) | 0.0041 (5) | 0.0059 (5) |
C18 | 0.0364 (7) | 0.0469 (9) | 0.0416 (8) | −0.0014 (6) | 0.0097 (6) | 0.0133 (7) |
C19 | 0.0478 (9) | 0.0547 (11) | 0.0567 (10) | 0.0158 (8) | 0.0169 (8) | 0.0109 (8) |
C20 | 0.0423 (7) | 0.0258 (7) | 0.0328 (7) | 0.0015 (5) | 0.0042 (5) | 0.0039 (5) |
C21 | 0.0561 (9) | 0.0358 (8) | 0.0368 (7) | −0.0023 (7) | 0.0055 (6) | 0.0084 (6) |
C22 | 0.0760 (12) | 0.0375 (9) | 0.0335 (7) | 0.0053 (8) | −0.0028 (7) | 0.0063 (6) |
C23 | 0.0516 (9) | 0.0430 (9) | 0.0476 (9) | 0.0111 (7) | −0.0103 (7) | −0.0004 (7) |
C24 | 0.0416 (8) | 0.0373 (8) | 0.0402 (8) | 0.0070 (6) | 0.0022 (6) | 0.0009 (6) |
C25 | 0.0948 (16) | 0.0362 (9) | 0.0540 (11) | 0.0184 (10) | −0.0106 (10) | −0.0076 (8) |
C26 | 0.0904 (16) | 0.0484 (11) | 0.0713 (13) | 0.0181 (11) | 0.0213 (12) | −0.0116 (10) |
C27 | 0.122 (2) | 0.0503 (12) | 0.0429 (10) | 0.0134 (12) | −0.0008 (12) | −0.0095 (9) |
C28 | 0.0866 (16) | 0.0472 (12) | 0.0813 (16) | −0.0079 (11) | −0.0144 (13) | −0.0178 (11) |
C29 | 0.116 (2) | 0.0349 (10) | 0.0681 (13) | −0.0096 (11) | 0.0222 (13) | −0.0052 (9) |
C30 | 0.0360 (7) | 0.0339 (7) | 0.0343 (7) | 0.0012 (6) | 0.0026 (5) | 0.0026 (6) |
C31 | 0.0330 (7) | 0.0399 (8) | 0.0340 (7) | 0.0051 (6) | 0.0042 (5) | 0.0051 (6) |
C32 | 0.0416 (8) | 0.0631 (12) | 0.0527 (9) | 0.0003 (8) | 0.0102 (7) | −0.0130 (8) |
C33 | 0.0474 (10) | 0.0894 (16) | 0.0589 (11) | 0.0020 (10) | 0.0213 (8) | −0.0131 (11) |
C34 | 0.0423 (9) | 0.0791 (14) | 0.0595 (11) | 0.0001 (9) | 0.0194 (8) | 0.0125 (10) |
C35 | 0.0469 (9) | 0.0459 (10) | 0.0655 (11) | −0.0037 (7) | 0.0129 (8) | 0.0134 (8) |
C36 | 0.0423 (8) | 0.0374 (8) | 0.0488 (8) | 0.0022 (6) | 0.0127 (6) | 0.0047 (7) |
N1 | 0.0363 (6) | 0.0336 (6) | 0.0331 (6) | −0.0005 (5) | 0.0037 (5) | 0.0023 (5) |
N2 | 0.0431 (7) | 0.0343 (7) | 0.0337 (6) | −0.0006 (5) | 0.0037 (5) | 0.0055 (5) |
N3 | 0.0369 (6) | 0.0386 (7) | 0.0359 (6) | 0.0032 (5) | 0.0101 (5) | 0.0066 (5) |
O1 | 0.0592 (7) | 0.0420 (7) | 0.0625 (8) | −0.0106 (6) | 0.0195 (6) | −0.0132 (6) |
Fe1 | 0.05287 (15) | 0.03087 (13) | 0.03530 (13) | 0.00303 (9) | 0.00166 (9) | −0.00061 (8) |
C1—C2 | 1.368 (2) | C20—C21 | 1.421 (2) |
C1—C6 | 1.405 (2) | C20—C24 | 1.424 (2) |
C1—H1 | 0.9300 | C20—Fe1 | 2.0393 (14) |
C2—C3 | 1.395 (3) | C21—C22 | 1.425 (2) |
C2—H2 | 0.9300 | C21—Fe1 | 2.0454 (17) |
C3—C4 | 1.362 (3) | C21—H21 | 0.9300 |
C3—H3 | 0.9300 | C22—C23 | 1.403 (3) |
C4—C5 | 1.410 (2) | C22—Fe1 | 2.0398 (17) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—N2 | 1.3727 (19) | C23—C24 | 1.423 (2) |
C5—C6 | 1.419 (2) | C23—Fe1 | 2.0430 (17) |
C6—N1 | 1.3777 (19) | C23—H23 | 0.9300 |
C7—N1 | 1.2975 (18) | C24—Fe1 | 2.0409 (16) |
C7—C8 | 1.4241 (18) | C24—H24 | 0.9300 |
C7—C11 | 1.5244 (19) | C25—C29 | 1.397 (4) |
C8—N2 | 1.3081 (18) | C25—C26 | 1.413 (3) |
C8—C9 | 1.459 (2) | C25—Fe1 | 2.0320 (19) |
C9—C15 | 1.3839 (19) | C25—H25 | 0.9300 |
C9—C10 | 1.397 (2) | C26—C27 | 1.398 (3) |
C10—C12 | 1.389 (2) | C26—Fe1 | 2.031 (2) |
C10—C11 | 1.5306 (19) | C26—H26 | 0.9300 |
C11—N3 | 1.4724 (18) | C27—C28 | 1.388 (4) |
C11—C16 | 1.5531 (18) | C27—Fe1 | 2.039 (2) |
C12—C13 | 1.388 (2) | C27—H27 | 0.9300 |
C12—H12 | 0.9300 | C28—C29 | 1.404 (3) |
C13—C14 | 1.379 (3) | C28—Fe1 | 2.041 (2) |
C13—H13 | 0.9300 | C28—H28 | 0.9300 |
C14—C15 | 1.380 (2) | C29—Fe1 | 2.035 (2) |
C14—H14 | 0.9300 | C29—H29 | 0.9300 |
C15—H15 | 0.9300 | C30—O1 | 1.2141 (19) |
C16—C30 | 1.523 (2) | C30—C31 | 1.498 (2) |
C16—C17 | 1.5428 (19) | C31—C36 | 1.390 (2) |
C16—H16 | 0.9800 | C31—C32 | 1.397 (2) |
C17—C20 | 1.5031 (19) | C32—C33 | 1.383 (3) |
C17—C18 | 1.537 (2) | C32—H32 | 0.9300 |
C17—H17 | 0.9800 | C33—C34 | 1.376 (3) |
C18—N3 | 1.458 (2) | C33—H33 | 0.9300 |
C18—H18A | 0.9700 | C34—C35 | 1.377 (3) |
C18—H18B | 0.9700 | C34—H34 | 0.9300 |
C19—N3 | 1.455 (2) | C35—C36 | 1.391 (2) |
C19—H19A | 0.9600 | C35—H35 | 0.9300 |
C19—H19B | 0.9600 | C36—H36 | 0.9300 |
C19—H19C | 0.9600 | ||
C2—C1—C6 | 120.49 (15) | C29—C25—C26 | 107.95 (19) |
C2—C1—H1 | 119.8 | C29—C25—Fe1 | 70.05 (12) |
C6—C1—H1 | 119.8 | C26—C25—Fe1 | 69.63 (11) |
C1—C2—C3 | 120.38 (16) | C29—C25—H25 | 126.0 |
C1—C2—H2 | 119.8 | C26—C25—H25 | 126.0 |
C3—C2—H2 | 119.8 | Fe1—C25—H25 | 125.9 |
C4—C3—C2 | 120.66 (16) | C27—C26—C25 | 107.3 (2) |
C4—C3—H3 | 119.7 | C27—C26—Fe1 | 70.21 (13) |
C2—C3—H3 | 119.7 | C25—C26—Fe1 | 69.68 (12) |
C3—C4—C5 | 120.61 (16) | C27—C26—H26 | 126.3 |
C3—C4—H4 | 119.7 | C25—C26—H26 | 126.3 |
C5—C4—H4 | 119.7 | Fe1—C26—H26 | 125.4 |
N2—C5—C4 | 119.40 (13) | C28—C27—C26 | 108.7 (2) |
N2—C5—C6 | 121.87 (13) | C28—C27—Fe1 | 70.20 (12) |
C4—C5—C6 | 118.71 (14) | C26—C27—Fe1 | 69.62 (12) |
N1—C6—C1 | 119.36 (13) | C28—C27—H27 | 125.6 |
N1—C6—C5 | 121.47 (13) | C26—C27—H27 | 125.6 |
C1—C6—C5 | 119.14 (14) | Fe1—C27—H27 | 126.1 |
N1—C7—C8 | 123.72 (13) | C27—C28—C29 | 108.1 (2) |
N1—C7—C11 | 125.80 (12) | C27—C28—Fe1 | 70.03 (13) |
C8—C7—C11 | 110.45 (12) | C29—C28—Fe1 | 69.63 (12) |
N2—C8—C7 | 123.33 (13) | C27—C28—H28 | 126.0 |
N2—C8—C9 | 128.60 (12) | C29—C28—H28 | 126.0 |
C7—C8—C9 | 108.02 (12) | Fe1—C28—H28 | 126.0 |
C15—C9—C10 | 121.37 (14) | C25—C29—C28 | 107.9 (2) |
C15—C9—C8 | 129.24 (14) | C25—C29—Fe1 | 69.78 (12) |
C10—C9—C8 | 109.37 (12) | C28—C29—Fe1 | 70.08 (13) |
C12—C10—C9 | 119.54 (13) | C25—C29—H29 | 126.0 |
C12—C10—C11 | 129.59 (13) | C28—C29—H29 | 126.0 |
C9—C10—C11 | 110.67 (12) | Fe1—C29—H29 | 125.7 |
N3—C11—C7 | 108.92 (12) | O1—C30—C31 | 119.77 (14) |
N3—C11—C10 | 114.60 (12) | O1—C30—C16 | 120.18 (14) |
C7—C11—C10 | 101.34 (11) | C31—C30—C16 | 120.04 (13) |
N3—C11—C16 | 100.40 (10) | C36—C31—C32 | 118.61 (15) |
C7—C11—C16 | 113.68 (11) | C36—C31—C30 | 123.70 (14) |
C10—C11—C16 | 118.13 (12) | C32—C31—C30 | 117.66 (15) |
C10—C12—C13 | 118.70 (15) | C33—C32—C31 | 120.51 (18) |
C10—C12—H12 | 120.6 | C33—C32—H32 | 119.7 |
C13—C12—H12 | 120.6 | C31—C32—H32 | 119.7 |
C14—C13—C12 | 121.21 (15) | C34—C33—C32 | 120.18 (18) |
C14—C13—H13 | 119.4 | C34—C33—H33 | 119.9 |
C12—C13—H13 | 119.4 | C32—C33—H33 | 119.9 |
C15—C14—C13 | 120.64 (15) | C33—C34—C35 | 120.27 (17) |
C15—C14—H14 | 119.7 | C33—C34—H34 | 119.9 |
C13—C14—H14 | 119.7 | C35—C34—H34 | 119.9 |
C14—C15—C9 | 118.53 (15) | C34—C35—C36 | 119.95 (18) |
C14—C15—H15 | 120.7 | C34—C35—H35 | 120.0 |
C9—C15—H15 | 120.7 | C36—C35—H35 | 120.0 |
C30—C16—C17 | 112.41 (12) | C31—C36—C35 | 120.48 (16) |
C30—C16—C11 | 115.39 (11) | C31—C36—H36 | 119.8 |
C17—C16—C11 | 104.26 (11) | C35—C36—H36 | 119.8 |
C30—C16—H16 | 108.2 | C7—N1—C6 | 114.88 (12) |
C17—C16—H16 | 108.2 | C8—N2—C5 | 114.69 (12) |
C11—C16—H16 | 108.2 | C19—N3—C18 | 113.81 (13) |
C20—C17—C18 | 115.40 (12) | C19—N3—C11 | 116.15 (12) |
C20—C17—C16 | 111.96 (11) | C18—N3—C11 | 107.73 (12) |
C18—C17—C16 | 104.99 (11) | C25—Fe1—C26 | 40.69 (9) |
C20—C17—H17 | 108.1 | C25—Fe1—C29 | 40.17 (10) |
C18—C17—H17 | 108.1 | C26—Fe1—C29 | 67.93 (11) |
C16—C17—H17 | 108.1 | C25—Fe1—C20 | 107.37 (7) |
N3—C18—C17 | 105.08 (11) | C26—Fe1—C20 | 123.10 (9) |
N3—C18—H18A | 110.7 | C29—Fe1—C20 | 122.47 (8) |
C17—C18—H18A | 110.7 | C25—Fe1—C22 | 157.98 (10) |
N3—C18—H18B | 110.7 | C26—Fe1—C22 | 122.02 (9) |
C17—C18—H18B | 110.7 | C29—Fe1—C22 | 160.21 (10) |
H18A—C18—H18B | 108.8 | C20—Fe1—C22 | 68.65 (6) |
N3—C19—H19A | 109.5 | C25—Fe1—C27 | 67.58 (8) |
N3—C19—H19B | 109.5 | C26—Fe1—C27 | 40.17 (10) |
H19A—C19—H19B | 109.5 | C29—Fe1—C27 | 67.37 (10) |
N3—C19—H19C | 109.5 | C20—Fe1—C27 | 159.57 (10) |
H19A—C19—H19C | 109.5 | C22—Fe1—C27 | 108.15 (8) |
H19B—C19—H19C | 109.5 | C25—Fe1—C28 | 67.55 (10) |
C21—C20—C24 | 107.48 (13) | C26—Fe1—C28 | 67.55 (11) |
C21—C20—C17 | 126.70 (14) | C29—Fe1—C28 | 40.28 (10) |
C24—C20—C17 | 125.70 (13) | C20—Fe1—C28 | 158.62 (10) |
C21—C20—Fe1 | 69.88 (9) | C22—Fe1—C28 | 123.98 (8) |
C24—C20—Fe1 | 69.64 (8) | C27—Fe1—C28 | 39.77 (11) |
C17—C20—Fe1 | 128.88 (10) | C25—Fe1—C23 | 160.48 (9) |
C20—C21—C22 | 107.87 (15) | C26—Fe1—C23 | 157.49 (9) |
C20—C21—Fe1 | 69.41 (9) | C29—Fe1—C23 | 124.55 (10) |
C22—C21—Fe1 | 69.38 (10) | C20—Fe1—C23 | 68.77 (6) |
C20—C21—H21 | 126.1 | C22—Fe1—C23 | 40.19 (8) |
C22—C21—H21 | 126.1 | C27—Fe1—C23 | 122.67 (8) |
Fe1—C21—H21 | 126.7 | C28—Fe1—C23 | 108.65 (9) |
C23—C22—C21 | 108.49 (14) | C25—Fe1—C24 | 123.92 (8) |
C23—C22—Fe1 | 70.03 (10) | C26—Fe1—C24 | 160.03 (8) |
C21—C22—Fe1 | 69.80 (9) | C29—Fe1—C24 | 108.51 (9) |
C23—C22—H22 | 125.8 | C20—Fe1—C24 | 40.84 (6) |
C21—C22—H22 | 125.8 | C22—Fe1—C24 | 68.12 (7) |
Fe1—C22—H22 | 126.0 | C27—Fe1—C24 | 158.44 (9) |
C22—C23—C24 | 107.97 (15) | C28—Fe1—C24 | 123.35 (10) |
C22—C23—Fe1 | 69.78 (10) | C23—Fe1—C24 | 40.78 (6) |
C24—C23—Fe1 | 69.53 (9) | C25—Fe1—C21 | 122.09 (9) |
C22—C23—H23 | 126.0 | C26—Fe1—C21 | 107.18 (9) |
C24—C23—H23 | 126.0 | C29—Fe1—C21 | 157.89 (9) |
Fe1—C23—H23 | 126.2 | C20—Fe1—C21 | 40.71 (6) |
C20—C24—C23 | 108.19 (15) | C22—Fe1—C21 | 40.82 (7) |
C20—C24—Fe1 | 69.52 (9) | C27—Fe1—C21 | 123.73 (10) |
C23—C24—Fe1 | 69.69 (10) | C28—Fe1—C21 | 159.79 (9) |
C20—C24—H24 | 125.9 | C23—Fe1—C21 | 68.28 (8) |
C23—C24—H24 | 125.9 | C24—Fe1—C21 | 68.29 (7) |
Fe1—C24—H24 | 126.5 | ||
C6—C1—C2—C3 | 0.1 (3) | C25—C26—Fe1—C22 | −161.76 (12) |
C1—C2—C3—C4 | −0.5 (3) | C25—C26—Fe1—C27 | 118.1 (2) |
C2—C3—C4—C5 | 0.1 (3) | C27—C26—Fe1—C28 | −36.90 (15) |
C3—C4—C5—N2 | 179.13 (16) | C25—C26—Fe1—C28 | 81.19 (15) |
C3—C4—C5—C6 | 0.6 (3) | C27—C26—Fe1—C23 | 47.7 (3) |
C2—C1—C6—N1 | −177.54 (15) | C25—C26—Fe1—C23 | 165.8 (2) |
C2—C1—C6—C5 | 0.6 (2) | C27—C26—Fe1—C24 | −164.1 (2) |
N2—C5—C6—N1 | −1.4 (2) | C25—C26—Fe1—C24 | −46.0 (3) |
C4—C5—C6—N1 | 177.16 (14) | C27—C26—Fe1—C21 | 122.34 (15) |
N2—C5—C6—C1 | −179.44 (14) | C25—C26—Fe1—C21 | −119.57 (13) |
C4—C5—C6—C1 | −0.9 (2) | C28—C29—Fe1—C25 | 118.8 (2) |
N1—C7—C8—N2 | −2.5 (2) | C25—C29—Fe1—C26 | −37.98 (13) |
C11—C7—C8—N2 | 175.52 (13) | C28—C29—Fe1—C26 | 80.85 (17) |
N1—C7—C8—C9 | 179.88 (13) | C25—C29—Fe1—C20 | 78.16 (14) |
C11—C7—C8—C9 | −2.13 (16) | C28—C29—Fe1—C20 | −163.01 (15) |
N2—C8—C9—C15 | 0.7 (3) | C25—C29—Fe1—C22 | −162.3 (2) |
C7—C8—C9—C15 | 178.24 (15) | C28—C29—Fe1—C22 | −43.4 (3) |
N2—C8—C9—C10 | −177.84 (15) | C25—C29—Fe1—C27 | −81.57 (15) |
C7—C8—C9—C10 | −0.34 (16) | C28—C29—Fe1—C27 | 37.26 (16) |
C15—C9—C10—C12 | −0.7 (2) | C25—C29—Fe1—C28 | −118.8 (2) |
C8—C9—C10—C12 | 178.05 (14) | C25—C29—Fe1—C23 | 163.40 (11) |
C15—C9—C10—C11 | −176.03 (14) | C28—C29—Fe1—C23 | −77.77 (18) |
C8—C9—C10—C11 | 2.67 (17) | C25—C29—Fe1—C24 | 121.06 (12) |
N1—C7—C11—N3 | 60.24 (18) | C28—C29—Fe1—C24 | −120.12 (16) |
C8—C7—C11—N3 | −117.69 (12) | C25—C29—Fe1—C21 | 43.3 (3) |
N1—C7—C11—C10 | −178.59 (14) | C28—C29—Fe1—C21 | 162.2 (2) |
C8—C7—C11—C10 | 3.48 (15) | C21—C20—Fe1—C25 | −119.34 (12) |
N1—C7—C11—C16 | −50.78 (19) | C24—C20—Fe1—C25 | 122.16 (11) |
C8—C7—C11—C16 | 131.29 (12) | C17—C20—Fe1—C25 | 2.14 (16) |
C12—C10—C11—N3 | −61.4 (2) | C21—C20—Fe1—C26 | −77.46 (13) |
C9—C10—C11—N3 | 113.40 (14) | C24—C20—Fe1—C26 | 164.04 (11) |
C12—C10—C11—C7 | −178.49 (15) | C17—C20—Fe1—C26 | 44.02 (17) |
C9—C10—C11—C7 | −3.70 (15) | C21—C20—Fe1—C29 | −160.75 (12) |
C12—C10—C11—C16 | 56.6 (2) | C24—C20—Fe1—C29 | 80.75 (13) |
C9—C10—C11—C16 | −128.57 (13) | C17—C20—Fe1—C29 | −39.27 (18) |
C9—C10—C12—C13 | −0.4 (2) | C21—C20—Fe1—C22 | 37.68 (10) |
C11—C10—C12—C13 | 174.02 (15) | C24—C20—Fe1—C22 | −80.82 (10) |
C10—C12—C13—C14 | 1.0 (3) | C17—C20—Fe1—C22 | 159.16 (16) |
C12—C13—C14—C15 | −0.6 (3) | C21—C20—Fe1—C27 | −47.1 (2) |
C13—C14—C15—C9 | −0.5 (3) | C24—C20—Fe1—C27 | −165.6 (2) |
C10—C9—C15—C14 | 1.1 (2) | C17—C20—Fe1—C27 | 74.4 (3) |
C8—C9—C15—C14 | −177.37 (15) | C21—C20—Fe1—C28 | 168.0 (2) |
N3—C11—C16—C30 | 159.56 (12) | C24—C20—Fe1—C28 | 49.5 (2) |
C7—C11—C16—C30 | −84.31 (15) | C17—C20—Fe1—C28 | −70.5 (3) |
C10—C11—C16—C30 | 34.24 (17) | C21—C20—Fe1—C23 | 80.96 (11) |
N3—C11—C16—C17 | 35.78 (13) | C24—C20—Fe1—C23 | −37.54 (10) |
C7—C11—C16—C17 | 151.92 (11) | C17—C20—Fe1—C23 | −157.56 (16) |
C10—C11—C16—C17 | −89.54 (14) | C21—C20—Fe1—C24 | 118.50 (13) |
C30—C16—C17—C20 | 90.90 (14) | C17—C20—Fe1—C24 | −120.02 (17) |
C11—C16—C17—C20 | −143.42 (12) | C24—C20—Fe1—C21 | −118.50 (13) |
C30—C16—C17—C18 | −143.18 (12) | C17—C20—Fe1—C21 | 121.48 (18) |
C11—C16—C17—C18 | −17.50 (14) | C23—C22—Fe1—C25 | 165.56 (18) |
C20—C17—C18—N3 | 115.98 (13) | C21—C22—Fe1—C25 | 46.0 (2) |
C16—C17—C18—N3 | −7.78 (15) | C23—C22—Fe1—C26 | −161.47 (12) |
C18—C17—C20—C21 | 40.0 (2) | C21—C22—Fe1—C26 | 78.98 (13) |
C16—C17—C20—C21 | 160.02 (14) | C23—C22—Fe1—C29 | −46.0 (3) |
C18—C17—C20—C24 | −144.52 (15) | C21—C22—Fe1—C29 | −165.6 (2) |
C16—C17—C20—C24 | −24.5 (2) | C23—C22—Fe1—C20 | 81.97 (10) |
C18—C17—C20—Fe1 | −52.85 (18) | C21—C22—Fe1—C20 | −37.58 (10) |
C16—C17—C20—Fe1 | 67.16 (17) | C23—C22—Fe1—C27 | −119.49 (13) |
C24—C20—C21—C22 | 0.84 (18) | C21—C22—Fe1—C27 | 120.96 (13) |
C17—C20—C21—C22 | 176.98 (14) | C23—C22—Fe1—C28 | −78.46 (15) |
Fe1—C20—C21—C22 | −58.91 (12) | C21—C22—Fe1—C28 | 161.99 (13) |
C24—C20—C21—Fe1 | 59.75 (10) | C21—C22—Fe1—C23 | −119.55 (14) |
C17—C20—C21—Fe1 | −124.11 (15) | C23—C22—Fe1—C24 | 37.89 (9) |
C20—C21—C22—C23 | −0.6 (2) | C21—C22—Fe1—C24 | −81.66 (11) |
Fe1—C21—C22—C23 | −59.55 (13) | C23—C22—Fe1—C21 | 119.55 (14) |
C20—C21—C22—Fe1 | 58.93 (11) | C28—C27—Fe1—C25 | −81.37 (16) |
C21—C22—C23—C24 | 0.2 (2) | C26—C27—Fe1—C25 | 38.47 (15) |
Fe1—C22—C23—C24 | −59.26 (12) | C28—C27—Fe1—C26 | −119.8 (2) |
C21—C22—C23—Fe1 | 59.41 (12) | C28—C27—Fe1—C29 | −37.72 (15) |
C21—C20—C24—C23 | −0.75 (18) | C26—C27—Fe1—C29 | 82.12 (16) |
C17—C20—C24—C23 | −176.94 (14) | C28—C27—Fe1—C20 | −160.86 (19) |
Fe1—C20—C24—C23 | 59.15 (11) | C26—C27—Fe1—C20 | −41.0 (3) |
C21—C20—C24—Fe1 | −59.90 (11) | C28—C27—Fe1—C22 | 121.69 (14) |
C17—C20—C24—Fe1 | 123.91 (14) | C26—C27—Fe1—C22 | −118.47 (15) |
C22—C23—C24—C20 | 0.37 (19) | C26—C27—Fe1—C28 | 119.8 (2) |
Fe1—C23—C24—C20 | −59.04 (11) | C28—C27—Fe1—C23 | 79.83 (16) |
C22—C23—C24—Fe1 | 59.41 (12) | C26—C27—Fe1—C23 | −160.33 (14) |
C29—C25—C26—C27 | 0.6 (2) | C28—C27—Fe1—C24 | 45.4 (3) |
Fe1—C25—C26—C27 | 60.41 (14) | C26—C27—Fe1—C24 | 165.26 (19) |
C29—C25—C26—Fe1 | −59.81 (14) | C28—C27—Fe1—C21 | 164.07 (13) |
C25—C26—C27—C28 | −0.6 (2) | C26—C27—Fe1—C21 | −76.09 (16) |
Fe1—C26—C27—C28 | 59.50 (16) | C27—C28—Fe1—C25 | 81.45 (15) |
C25—C26—C27—Fe1 | −60.07 (14) | C29—C28—Fe1—C25 | −37.69 (15) |
C26—C27—C28—C29 | 0.3 (2) | C27—C28—Fe1—C26 | 37.26 (14) |
Fe1—C27—C28—C29 | 59.46 (15) | C29—C28—Fe1—C26 | −81.88 (17) |
C26—C27—C28—Fe1 | −59.15 (15) | C27—C28—Fe1—C29 | 119.1 (2) |
C26—C25—C29—C28 | −0.4 (2) | C27—C28—Fe1—C20 | 161.70 (18) |
Fe1—C25—C29—C28 | −59.96 (15) | C29—C28—Fe1—C20 | 42.6 (3) |
C26—C25—C29—Fe1 | 59.55 (14) | C27—C28—Fe1—C22 | −77.16 (16) |
C27—C28—C29—C25 | 0.1 (2) | C29—C28—Fe1—C22 | 163.70 (15) |
Fe1—C28—C29—C25 | 59.77 (15) | C29—C28—Fe1—C27 | −119.1 (2) |
C27—C28—C29—Fe1 | −59.71 (16) | C27—C28—Fe1—C23 | −119.02 (14) |
C17—C16—C30—O1 | 31.91 (18) | C29—C28—Fe1—C23 | 121.84 (16) |
C11—C16—C30—O1 | −87.47 (17) | C27—C28—Fe1—C24 | −161.74 (12) |
C17—C16—C30—C31 | −146.91 (12) | C29—C28—Fe1—C24 | 79.11 (17) |
C11—C16—C30—C31 | 93.71 (15) | C27—C28—Fe1—C21 | −41.4 (3) |
O1—C30—C31—C36 | −175.78 (15) | C29—C28—Fe1—C21 | −160.5 (2) |
C16—C30—C31—C36 | 3.0 (2) | C22—C23—Fe1—C25 | −163.8 (2) |
O1—C30—C31—C32 | 2.3 (2) | C24—C23—Fe1—C25 | −44.5 (3) |
C16—C30—C31—C32 | −178.92 (13) | C22—C23—Fe1—C26 | 44.8 (3) |
C36—C31—C32—C33 | 0.2 (3) | C24—C23—Fe1—C26 | 164.0 (2) |
C30—C31—C32—C33 | −177.96 (17) | C22—C23—Fe1—C29 | 162.79 (11) |
C31—C32—C33—C34 | −0.3 (3) | C24—C23—Fe1—C29 | −77.98 (13) |
C32—C33—C34—C35 | 0.4 (3) | C22—C23—Fe1—C20 | −81.63 (10) |
C33—C34—C35—C36 | −0.3 (3) | C24—C23—Fe1—C20 | 37.60 (10) |
C32—C31—C36—C35 | −0.1 (2) | C24—C23—Fe1—C22 | 119.23 (15) |
C30—C31—C36—C35 | 177.97 (14) | C22—C23—Fe1—C27 | 79.31 (14) |
C34—C35—C36—C31 | 0.1 (3) | C24—C23—Fe1—C27 | −161.46 (13) |
C8—C7—N1—C6 | 1.1 (2) | C22—C23—Fe1—C28 | 120.96 (13) |
C11—C7—N1—C6 | −176.57 (13) | C24—C23—Fe1—C28 | −119.81 (13) |
C1—C6—N1—C7 | 178.75 (13) | C22—C23—Fe1—C24 | −119.23 (15) |
C5—C6—N1—C7 | 0.7 (2) | C22—C23—Fe1—C21 | −37.74 (10) |
C7—C8—N2—C5 | 1.7 (2) | C24—C23—Fe1—C21 | 81.49 (11) |
C9—C8—N2—C5 | 178.80 (14) | C20—C24—Fe1—C25 | −76.82 (13) |
C4—C5—N2—C8 | −178.38 (15) | C23—C24—Fe1—C25 | 163.60 (13) |
C6—C5—N2—C8 | 0.1 (2) | C20—C24—Fe1—C26 | −42.4 (3) |
C17—C18—N3—C19 | 162.64 (13) | C23—C24—Fe1—C26 | −162.0 (2) |
C17—C18—N3—C11 | 32.35 (15) | C20—C24—Fe1—C29 | −118.58 (11) |
C7—C11—N3—C19 | 68.72 (17) | C23—C24—Fe1—C29 | 121.84 (13) |
C10—C11—N3—C19 | −43.96 (18) | C23—C24—Fe1—C20 | −119.58 (14) |
C16—C11—N3—C19 | −171.64 (14) | C20—C24—Fe1—C22 | 82.22 (10) |
C7—C11—N3—C18 | −162.30 (11) | C23—C24—Fe1—C22 | −37.36 (11) |
C10—C11—N3—C18 | 85.02 (14) | C20—C24—Fe1—C27 | 166.3 (2) |
C16—C11—N3—C18 | −42.66 (14) | C23—C24—Fe1—C27 | 46.7 (3) |
C29—C25—Fe1—C26 | 118.98 (19) | C20—C24—Fe1—C28 | −160.61 (11) |
C26—C25—Fe1—C29 | −118.98 (19) | C23—C24—Fe1—C28 | 79.81 (14) |
C29—C25—Fe1—C20 | −120.09 (13) | C20—C24—Fe1—C23 | 119.58 (14) |
C26—C25—Fe1—C20 | 120.93 (14) | C20—C24—Fe1—C21 | 38.10 (8) |
C29—C25—Fe1—C22 | 164.03 (18) | C23—C24—Fe1—C21 | −81.48 (11) |
C26—C25—Fe1—C22 | 45.1 (3) | C20—C21—Fe1—C25 | 79.13 (12) |
C29—C25—Fe1—C27 | 80.98 (15) | C22—C21—Fe1—C25 | −161.43 (12) |
C26—C25—Fe1—C27 | −37.99 (15) | C20—C21—Fe1—C26 | 121.14 (11) |
C29—C25—Fe1—C28 | 37.80 (14) | C22—C21—Fe1—C26 | −119.42 (12) |
C26—C25—Fe1—C28 | −81.18 (16) | C20—C21—Fe1—C29 | 47.6 (3) |
C29—C25—Fe1—C23 | −44.7 (3) | C22—C21—Fe1—C29 | 167.1 (2) |
C26—C25—Fe1—C23 | −163.7 (2) | C22—C21—Fe1—C20 | 119.44 (15) |
C29—C25—Fe1—C24 | −78.24 (14) | C20—C21—Fe1—C22 | −119.44 (15) |
C26—C25—Fe1—C24 | 162.78 (13) | C20—C21—Fe1—C27 | 162.09 (11) |
C29—C25—Fe1—C21 | −162.25 (12) | C22—C21—Fe1—C27 | −78.47 (14) |
C26—C25—Fe1—C21 | 78.77 (15) | C20—C21—Fe1—C28 | −167.4 (2) |
C27—C26—Fe1—C25 | −118.1 (2) | C22—C21—Fe1—C28 | −47.9 (3) |
C27—C26—Fe1—C29 | −80.59 (16) | C20—C21—Fe1—C23 | −82.26 (10) |
C25—C26—Fe1—C29 | 37.51 (13) | C22—C21—Fe1—C23 | 37.18 (11) |
C27—C26—Fe1—C20 | 164.13 (13) | C20—C21—Fe1—C24 | −38.22 (9) |
C25—C26—Fe1—C20 | −77.78 (15) | C22—C21—Fe1—C24 | 81.23 (11) |
C27—C26—Fe1—C22 | 80.15 (17) |
Cg3 is the centroid of the C20–C24 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···N3 | 0.93 | 2.55 | 3.351 (2) | 144 |
C35—H35···Cg3i | 0.93 | 2.83 | 3.616 (2) | 143 |
Symmetry code: (i) −x+2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C31H24N3O)] |
Mr | 575.47 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.8091 (18), 12.326 (2), 20.989 (3) |
β (°) | 100.654 (8) |
V (Å3) | 2748.2 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.58 |
Crystal size (mm) | 0.2 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.890, 0.890 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27206, 6927, 5624 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.673 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.106, 1.01 |
No. of reflections | 6927 |
No. of parameters | 371 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.44 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg3 is the centroid of the C20–C24 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···N3 | 0.93 | 2.55 | 3.351 (2) | 144 |
C35—H35···Cg3i | 0.93 | 2.83 | 3.616 (2) | 143 |
Symmetry code: (i) −x+2, y+1/2, −z+3/2. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. BV also thanks the University Grants Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship.
References
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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 are well known to have biological activities like antimalarial, antifungal (Biot et al., 2004), antitumor (Jaouen et al., 2004), and antibacterial (Fouda et al., 2007). Against this background, the information of molecular conformations and crystal packing of title compound was obtained and analyzed using X-ray diffraction study. The bond lengths and angles of titled compound agree with those observed in other ferrocene derivative 3'-Ferrocenylcarbonyl-1'-methyl-4'- phenylspiro[indeno[2,3-b]quinoxaline-11,2'-pyrrolidine] (Vijayakumar et al. 2012).
The pyrrolidine ring adopts a twisted conformation with the puckering parameters q2 and ϕ and the smallest displacement asymmetric parameters, δ, as follows: q2 = 0.399 (1) A, ϕ = 26.0 (2)° and Δ2(C17) =7.29 (14)°. The dihedral angle between the pyrrolidine ring and indeno-quinoxaline ring system is 84.44 (5)° which clearly shows that the both rings are almost perpendicular to each other. The Cg3 (C20—C24) and Cg4 (C25—C29) are the centroids cyclopentadinene rings where the Fe1-Cg3 and Fe1-Cg4 distances are 1.6466 (8) and 1.6512 (10) Å, respectively and the Cg3-Fe1-Cg4 angle is 179.40 (5)°. In addition to the van der Waals interactions, the crystal packing (Fig.2) is stabilized by weak C—H···N and C—H···π interactions (Table 1).