metal-organic compounds
3′-Ferrocenylcarbonyl-1′-methyl-4′-phenylspiro[indeno[2,3-b]quinoxaline-11,2′-pyrrolidine]
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 makes a dihedral angle of 86.3 (3)° with the mean plane [r.m.s deviation = 0.074 (2) Å] of the indeno-quinoxaline ring system. The central pyrrolidine ring adopts a twist conformation and the two cyclopentadienyl rings adopt an eclipsed conformation. In the crystal, molecules are linked by weak C—H⋯N and C—H⋯π interactions, propagating along the c and a axes, respectively.
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); 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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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
10.1107/S1600536812042468/lx2263sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042468/lx2263Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812042468/lx2263Isup4.mol
A mixture of ninhydrin (1 mM) and 1,2-phenylenediamine (1 mM) was stirred with 10 ml 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 = 0.93Å and refined using the riding model approximation with a fixed isotropic displacement parameter of Uiso(H) = 1.2Ueq(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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).[Fe(C5H5)(C31H24N3O)] | F(000) = 1200 |
Mr = 575.47 | Dx = 1.373 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7107 reflections |
a = 11.1008 (4) Å | θ = 1.9–28.7° |
b = 11.9156 (5) Å | µ = 0.58 mm−1 |
c = 21.0511 (9) Å | T = 293 K |
β = 90.944 (2)° | Block, brown |
V = 2784.11 (19) Å3 | 0.2 × 0.2 × 0.2 mm |
Z = 4 |
Bruker SMART APEX2 area-detector diffractometer | 4920 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 28.7°, θmin = 1.9° |
ω and ϕ scans | h = −14→14 |
26663 measured reflections | k = −16→14 |
7107 independent reflections | l = −28→22 |
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)] = 0.038 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0445P)2 + 1.0601P] where P = (Fo2 + 2Fc2)/3 |
7107 reflections | (Δ/σ)max < 0.001 |
370 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[Fe(C5H5)(C31H24N3O)] | V = 2784.11 (19) Å3 |
Mr = 575.47 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.1008 (4) Å | µ = 0.58 mm−1 |
b = 11.9156 (5) Å | T = 293 K |
c = 21.0511 (9) Å | 0.2 × 0.2 × 0.2 mm |
β = 90.944 (2)° |
Bruker SMART APEX2 area-detector diffractometer | 4920 reflections with I > 2σ(I) |
26663 measured reflections | Rint = 0.027 |
7107 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.34 e Å−3 |
7107 reflections | Δρmin = −0.31 e Å−3 |
370 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 | 0.77481 (19) | 0.11847 (19) | −0.10565 (10) | 0.0523 (5) | |
H1 | 0.7105 | 0.0704 | −0.0983 | 0.063* | |
C2 | 0.8184 (2) | 0.1304 (2) | −0.16573 (10) | 0.0639 (7) | |
H2 | 0.7842 | 0.0896 | −0.1991 | 0.077* | |
C3 | 0.9136 (2) | 0.2032 (2) | −0.17707 (11) | 0.0683 (7) | |
H3 | 0.9429 | 0.2099 | −0.2180 | 0.082* | |
C4 | 0.9646 (2) | 0.2648 (2) | −0.12949 (11) | 0.0654 (7) | |
H4 | 1.0267 | 0.3146 | −0.1383 | 0.079* | |
C5 | 0.92353 (18) | 0.25338 (18) | −0.06672 (10) | 0.0493 (5) | |
C6 | 0.82739 (17) | 0.17886 (17) | −0.05517 (9) | 0.0433 (4) | |
C7 | 0.84103 (15) | 0.21853 (15) | 0.04944 (9) | 0.0375 (4) | |
C8 | 0.93787 (16) | 0.29346 (16) | 0.03778 (10) | 0.0427 (4) | |
C9 | 0.98033 (16) | 0.33888 (16) | 0.09867 (10) | 0.0446 (5) | |
C10 | 0.91387 (15) | 0.28947 (16) | 0.14705 (9) | 0.0393 (4) | |
C11 | 0.81387 (15) | 0.21463 (15) | 0.12047 (8) | 0.0344 (4) | |
C12 | 0.94162 (17) | 0.31364 (18) | 0.20968 (10) | 0.0490 (5) | |
H12 | 0.9004 | 0.2788 | 0.2423 | 0.059* | |
C13 | 1.03199 (19) | 0.3908 (2) | 0.22318 (12) | 0.0606 (6) | |
H13 | 1.0509 | 0.4080 | 0.2653 | 0.073* | |
C14 | 1.0946 (2) | 0.4425 (2) | 0.17492 (14) | 0.0661 (7) | |
H14 | 1.1533 | 0.4956 | 0.1849 | 0.079* | |
C15 | 1.07068 (18) | 0.41605 (19) | 0.11241 (13) | 0.0601 (6) | |
H15 | 1.1142 | 0.4492 | 0.0800 | 0.072* | |
C16 | 0.68110 (14) | 0.25706 (14) | 0.13186 (8) | 0.0319 (4) | |
H16 | 0.6470 | 0.2828 | 0.0912 | 0.038* | |
C17 | 0.60983 (15) | 0.15244 (15) | 0.15325 (9) | 0.0377 (4) | |
H17 | 0.5996 | 0.1567 | 0.1993 | 0.045* | |
C18 | 0.69421 (17) | 0.05554 (16) | 0.13916 (10) | 0.0433 (4) | |
H18A | 0.6803 | −0.0071 | 0.1675 | 0.052* | |
H18B | 0.6844 | 0.0303 | 0.0956 | 0.052* | |
C19 | 0.91265 (19) | 0.03021 (19) | 0.13435 (12) | 0.0611 (6) | |
H19A | 0.9875 | 0.0682 | 0.1428 | 0.092* | |
H19B | 0.9074 | 0.0106 | 0.0902 | 0.092* | |
H19C | 0.9089 | −0.0367 | 0.1597 | 0.092* | |
C20 | 0.48572 (16) | 0.14804 (15) | 0.12174 (10) | 0.0422 (4) | |
C21 | 0.38282 (18) | 0.16230 (18) | 0.15700 (12) | 0.0574 (6) | |
H21 | 0.3889 | 0.1662 | 0.2011 | 0.069* | |
C22 | 0.2701 (2) | 0.1709 (2) | 0.12730 (16) | 0.0743 (8) | |
H22 | 0.2019 | 0.1822 | 0.1516 | 0.089* | |
C23 | 0.2592 (2) | 0.1628 (2) | 0.06276 (17) | 0.0775 (8) | |
H23 | 0.1840 | 0.1694 | 0.0430 | 0.093* | |
C24 | 0.3599 (2) | 0.1448 (2) | 0.02715 (13) | 0.0665 (7) | |
H24 | 0.3526 | 0.1372 | −0.0167 | 0.080* | |
C25 | 0.47266 (19) | 0.13794 (18) | 0.05648 (11) | 0.0522 (5) | |
H25 | 0.5404 | 0.1264 | 0.0319 | 0.063* | |
C26 | 0.67864 (14) | 0.35423 (15) | 0.17847 (8) | 0.0334 (4) | |
C27 | 0.70406 (14) | 0.46598 (15) | 0.15256 (8) | 0.0338 (4) | |
C28 | 0.71680 (15) | 0.49567 (16) | 0.08699 (9) | 0.0386 (4) | |
H28 | 0.7184 | 0.4435 | 0.0510 | 0.046* | |
C29 | 0.72666 (18) | 0.61355 (18) | 0.08356 (10) | 0.0495 (5) | |
H29 | 0.7344 | 0.6578 | 0.0446 | 0.059* | |
C30 | 0.72074 (18) | 0.65705 (17) | 0.14583 (11) | 0.0503 (5) | |
H30 | 0.7234 | 0.7368 | 0.1572 | 0.060* | |
C31 | 0.70684 (16) | 0.56730 (16) | 0.18877 (9) | 0.0416 (4) | |
H31 | 0.7005 | 0.5734 | 0.2350 | 0.050* | |
C32 | 0.41038 (19) | 0.4857 (3) | 0.14284 (15) | 0.0736 (8) | |
H32 | 0.4028 | 0.4107 | 0.1615 | 0.088* | |
C33 | 0.4164 (2) | 0.5871 (4) | 0.17646 (15) | 0.0895 (10) | |
H33 | 0.4130 | 0.5960 | 0.2227 | 0.107* | |
C34 | 0.4264 (2) | 0.6725 (3) | 0.1322 (2) | 0.0933 (11) | |
H34 | 0.4319 | 0.7528 | 0.1421 | 0.112* | |
C35 | 0.4259 (2) | 0.6263 (3) | 0.07184 (15) | 0.0805 (8) | |
H35 | 0.4313 | 0.6679 | 0.0318 | 0.097* | |
C36 | 0.41605 (19) | 0.5102 (2) | 0.07812 (13) | 0.0672 (7) | |
H36 | 0.4137 | 0.4555 | 0.0433 | 0.081* | |
N1 | 0.78365 (14) | 0.16272 (13) | 0.00513 (7) | 0.0405 (4) | |
N2 | 0.97974 (15) | 0.31325 (16) | −0.01893 (9) | 0.0536 (4) | |
N3 | 0.81296 (13) | 0.10361 (13) | 0.15009 (7) | 0.0407 (4) | |
O1 | 0.65943 (13) | 0.33960 (12) | 0.23460 (6) | 0.0482 (3) | |
Fe1 | 0.56726 (2) | 0.56669 (2) | 0.124750 (13) | 0.03939 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0551 (12) | 0.0581 (13) | 0.0439 (12) | 0.0195 (10) | 0.0050 (9) | 0.0000 (10) |
C2 | 0.0678 (15) | 0.0819 (18) | 0.0420 (12) | 0.0347 (14) | 0.0023 (10) | −0.0004 (12) |
C3 | 0.0685 (15) | 0.0936 (19) | 0.0435 (13) | 0.0377 (14) | 0.0174 (11) | 0.0164 (13) |
C4 | 0.0572 (13) | 0.0820 (18) | 0.0577 (15) | 0.0201 (12) | 0.0216 (11) | 0.0225 (13) |
C5 | 0.0432 (10) | 0.0556 (13) | 0.0497 (12) | 0.0170 (9) | 0.0140 (9) | 0.0113 (10) |
C6 | 0.0434 (10) | 0.0452 (11) | 0.0414 (10) | 0.0182 (8) | 0.0078 (8) | 0.0061 (9) |
C7 | 0.0330 (8) | 0.0362 (10) | 0.0434 (10) | 0.0087 (7) | 0.0077 (7) | 0.0053 (8) |
C8 | 0.0336 (9) | 0.0404 (10) | 0.0543 (12) | 0.0059 (8) | 0.0107 (8) | 0.0096 (9) |
C9 | 0.0306 (9) | 0.0417 (11) | 0.0615 (13) | 0.0037 (8) | 0.0045 (8) | 0.0042 (9) |
C10 | 0.0279 (8) | 0.0385 (10) | 0.0514 (11) | 0.0056 (7) | −0.0009 (7) | 0.0031 (8) |
C11 | 0.0316 (8) | 0.0339 (9) | 0.0378 (9) | 0.0045 (7) | 0.0026 (7) | 0.0028 (7) |
C12 | 0.0374 (10) | 0.0531 (12) | 0.0564 (12) | 0.0010 (9) | −0.0065 (9) | 0.0032 (10) |
C13 | 0.0466 (11) | 0.0628 (14) | 0.0717 (15) | −0.0017 (11) | −0.0159 (11) | −0.0051 (12) |
C14 | 0.0420 (11) | 0.0597 (15) | 0.096 (2) | −0.0083 (10) | −0.0108 (12) | −0.0055 (14) |
C15 | 0.0394 (11) | 0.0545 (14) | 0.0867 (18) | −0.0055 (9) | 0.0071 (11) | 0.0078 (12) |
C16 | 0.0299 (8) | 0.0332 (9) | 0.0327 (9) | 0.0012 (7) | 0.0025 (7) | 0.0034 (7) |
C17 | 0.0371 (9) | 0.0377 (10) | 0.0385 (10) | −0.0044 (7) | 0.0038 (7) | 0.0013 (8) |
C18 | 0.0472 (10) | 0.0340 (10) | 0.0488 (11) | −0.0009 (8) | 0.0002 (8) | 0.0074 (8) |
C19 | 0.0513 (12) | 0.0470 (12) | 0.0850 (17) | 0.0180 (10) | 0.0033 (11) | 0.0110 (12) |
C20 | 0.0355 (9) | 0.0340 (10) | 0.0571 (12) | −0.0054 (7) | 0.0025 (8) | −0.0009 (9) |
C21 | 0.0443 (11) | 0.0502 (13) | 0.0781 (16) | −0.0082 (9) | 0.0112 (11) | −0.0151 (11) |
C22 | 0.0372 (11) | 0.0623 (16) | 0.124 (2) | −0.0028 (10) | 0.0095 (13) | −0.0171 (16) |
C23 | 0.0457 (13) | 0.0585 (16) | 0.128 (3) | −0.0015 (11) | −0.0218 (15) | 0.0000 (16) |
C24 | 0.0657 (15) | 0.0541 (14) | 0.0789 (17) | −0.0064 (11) | −0.0237 (13) | 0.0039 (12) |
C25 | 0.0477 (11) | 0.0501 (12) | 0.0586 (13) | −0.0039 (9) | −0.0048 (9) | 0.0019 (10) |
C26 | 0.0275 (8) | 0.0391 (10) | 0.0338 (9) | 0.0038 (7) | 0.0000 (6) | 0.0002 (7) |
C27 | 0.0288 (8) | 0.0362 (9) | 0.0362 (9) | 0.0031 (7) | −0.0007 (7) | −0.0018 (7) |
C28 | 0.0363 (9) | 0.0404 (10) | 0.0392 (10) | 0.0027 (8) | 0.0042 (7) | 0.0004 (8) |
C29 | 0.0471 (11) | 0.0432 (11) | 0.0585 (13) | −0.0021 (9) | 0.0059 (9) | 0.0116 (10) |
C30 | 0.0491 (11) | 0.0350 (10) | 0.0669 (14) | −0.0044 (9) | 0.0014 (10) | −0.0063 (10) |
C31 | 0.0367 (9) | 0.0420 (10) | 0.0459 (11) | −0.0007 (8) | −0.0044 (8) | −0.0069 (9) |
C32 | 0.0334 (11) | 0.089 (2) | 0.099 (2) | −0.0029 (12) | 0.0050 (12) | 0.0158 (17) |
C33 | 0.0390 (12) | 0.150 (3) | 0.080 (2) | 0.0184 (16) | 0.0089 (12) | −0.033 (2) |
C34 | 0.0580 (16) | 0.074 (2) | 0.147 (3) | 0.0346 (14) | −0.0232 (18) | −0.034 (2) |
C35 | 0.0606 (15) | 0.086 (2) | 0.094 (2) | 0.0177 (14) | −0.0286 (14) | 0.0182 (17) |
C36 | 0.0403 (11) | 0.0840 (19) | 0.0768 (17) | 0.0036 (11) | −0.0131 (11) | −0.0211 (15) |
N1 | 0.0418 (8) | 0.0402 (9) | 0.0399 (9) | 0.0067 (7) | 0.0073 (7) | 0.0024 (7) |
N2 | 0.0442 (9) | 0.0584 (11) | 0.0588 (11) | 0.0042 (8) | 0.0167 (8) | 0.0134 (9) |
N3 | 0.0393 (8) | 0.0342 (8) | 0.0485 (9) | 0.0050 (6) | 0.0009 (7) | 0.0080 (7) |
O1 | 0.0615 (8) | 0.0496 (8) | 0.0336 (7) | 0.0017 (7) | 0.0078 (6) | 0.0009 (6) |
Fe1 | 0.03474 (14) | 0.03809 (16) | 0.04522 (17) | 0.00631 (11) | −0.00323 (11) | −0.00167 (12) |
C1—C2 | 1.369 (3) | C20—C21 | 1.383 (3) |
C1—C6 | 1.403 (3) | C20—C25 | 1.384 (3) |
C1—H1 | 0.9300 | C21—C22 | 1.393 (3) |
C2—C3 | 1.392 (4) | C21—H21 | 0.9300 |
C2—H2 | 0.9300 | C22—C23 | 1.365 (4) |
C3—C4 | 1.358 (4) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C23—C24 | 1.373 (4) |
C4—C5 | 1.412 (3) | C23—H23 | 0.9300 |
C4—H4 | 0.9300 | C24—C25 | 1.389 (3) |
C5—N2 | 1.375 (3) | C24—H24 | 0.9300 |
C5—C6 | 1.412 (3) | C25—H25 | 0.9300 |
C6—N1 | 1.380 (2) | C26—O1 | 1.217 (2) |
C7—N1 | 1.303 (2) | C26—C27 | 1.468 (2) |
C7—C8 | 1.422 (3) | C27—C31 | 1.428 (3) |
C7—C11 | 1.531 (2) | C27—C28 | 1.434 (2) |
C8—N2 | 1.310 (2) | C27—Fe1 | 2.0148 (16) |
C8—C9 | 1.462 (3) | C28—C29 | 1.411 (3) |
C9—C15 | 1.388 (3) | C28—Fe1 | 2.0364 (17) |
C9—C10 | 1.397 (3) | C28—H28 | 0.9800 |
C10—C12 | 1.379 (3) | C29—C30 | 1.412 (3) |
C10—C11 | 1.523 (2) | C29—Fe1 | 2.060 (2) |
C11—N3 | 1.462 (2) | C29—H29 | 0.9800 |
C11—C16 | 1.580 (2) | C30—C31 | 1.410 (3) |
C12—C13 | 1.387 (3) | C30—Fe1 | 2.058 (2) |
C12—H12 | 0.9300 | C30—H30 | 0.9800 |
C13—C14 | 1.385 (3) | C31—Fe1 | 2.0367 (18) |
C13—H13 | 0.9300 | C31—H31 | 0.9800 |
C14—C15 | 1.375 (3) | C32—C36 | 1.396 (4) |
C14—H14 | 0.9300 | C32—C33 | 1.401 (4) |
C15—H15 | 0.9300 | C32—Fe1 | 2.033 (2) |
C16—C26 | 1.518 (2) | C32—H32 | 0.9800 |
C16—C17 | 1.547 (2) | C33—C34 | 1.385 (5) |
C16—H16 | 0.9800 | C33—Fe1 | 2.026 (2) |
C17—C18 | 1.519 (3) | C33—H33 | 0.9800 |
C17—C20 | 1.520 (2) | C34—C35 | 1.386 (4) |
C17—H17 | 0.9800 | C34—Fe1 | 2.017 (2) |
C18—N3 | 1.452 (2) | C34—H34 | 0.9800 |
C18—H18A | 0.9700 | C35—C36 | 1.395 (4) |
C18—H18B | 0.9700 | C35—Fe1 | 2.037 (2) |
C19—N3 | 1.453 (2) | C35—H35 | 0.9800 |
C19—H19A | 0.9600 | C36—Fe1 | 2.045 (2) |
C19—H19B | 0.9600 | C36—H36 | 0.9800 |
C19—H19C | 0.9600 | ||
C2—C1—C6 | 119.9 (2) | C29—C28—H28 | 126.2 |
C2—C1—H1 | 120.1 | C27—C28—H28 | 126.2 |
C6—C1—H1 | 120.1 | Fe1—C28—H28 | 126.2 |
C1—C2—C3 | 120.3 (2) | C28—C29—C30 | 108.25 (18) |
C1—C2—H2 | 119.9 | C28—C29—Fe1 | 68.95 (11) |
C3—C2—H2 | 119.9 | C30—C29—Fe1 | 69.84 (11) |
C4—C3—C2 | 121.3 (2) | C28—C29—H29 | 125.9 |
C4—C3—H3 | 119.4 | C30—C29—H29 | 125.9 |
C2—C3—H3 | 119.4 | Fe1—C29—H29 | 125.9 |
C3—C4—C5 | 120.1 (2) | C31—C30—C29 | 108.90 (18) |
C3—C4—H4 | 120.0 | C31—C30—Fe1 | 69.05 (11) |
C5—C4—H4 | 120.0 | C29—C30—Fe1 | 70.05 (11) |
N2—C5—C4 | 119.0 (2) | C31—C30—H30 | 125.5 |
N2—C5—C6 | 122.38 (18) | C29—C30—H30 | 125.5 |
C4—C5—C6 | 118.6 (2) | Fe1—C30—H30 | 125.5 |
N1—C6—C1 | 118.49 (19) | C30—C31—C27 | 107.50 (17) |
N1—C6—C5 | 121.62 (18) | C30—C31—Fe1 | 70.65 (11) |
C1—C6—C5 | 119.89 (19) | C27—C31—Fe1 | 68.55 (9) |
N1—C7—C8 | 123.99 (17) | C30—C31—H31 | 126.2 |
N1—C7—C11 | 125.57 (16) | C27—C31—H31 | 126.2 |
C8—C7—C11 | 110.44 (16) | Fe1—C31—H31 | 126.2 |
N2—C8—C7 | 123.44 (19) | C36—C32—C33 | 108.1 (3) |
N2—C8—C9 | 128.20 (18) | C36—C32—Fe1 | 70.45 (14) |
C7—C8—C9 | 108.35 (16) | C33—C32—Fe1 | 69.57 (15) |
C15—C9—C10 | 121.0 (2) | C36—C32—H32 | 126.0 |
C15—C9—C8 | 130.5 (2) | C33—C32—H32 | 126.0 |
C10—C9—C8 | 108.45 (16) | Fe1—C32—H32 | 126.0 |
C12—C10—C9 | 119.76 (18) | C34—C33—C32 | 107.4 (3) |
C12—C10—C11 | 128.55 (17) | C34—C33—Fe1 | 69.61 (16) |
C9—C10—C11 | 111.67 (16) | C32—C33—Fe1 | 70.04 (14) |
N3—C11—C10 | 112.52 (14) | C34—C33—H33 | 126.3 |
N3—C11—C7 | 116.54 (15) | C32—C33—H33 | 126.3 |
C10—C11—C7 | 100.77 (14) | Fe1—C33—H33 | 126.3 |
N3—C11—C16 | 102.23 (13) | C33—C34—C35 | 109.0 (3) |
C10—C11—C16 | 115.65 (14) | C33—C34—Fe1 | 70.33 (15) |
C7—C11—C16 | 109.73 (13) | C35—C34—Fe1 | 70.78 (15) |
C10—C12—C13 | 118.9 (2) | C33—C34—H34 | 125.5 |
C10—C12—H12 | 120.5 | C35—C34—H34 | 125.5 |
C13—C12—H12 | 120.5 | Fe1—C34—H34 | 125.5 |
C14—C13—C12 | 121.0 (2) | C34—C35—C36 | 107.9 (3) |
C14—C13—H13 | 119.5 | C34—C35—Fe1 | 69.25 (14) |
C12—C13—H13 | 119.5 | C36—C35—Fe1 | 70.31 (13) |
C15—C14—C13 | 120.6 (2) | C34—C35—H35 | 126.1 |
C15—C14—H14 | 119.7 | C36—C35—H35 | 126.1 |
C13—C14—H14 | 119.7 | Fe1—C35—H35 | 126.1 |
C14—C15—C9 | 118.6 (2) | C35—C36—C32 | 107.7 (3) |
C14—C15—H15 | 120.7 | C35—C36—Fe1 | 69.72 (14) |
C9—C15—H15 | 120.7 | C32—C36—Fe1 | 69.52 (13) |
C26—C16—C17 | 114.31 (14) | C35—C36—H36 | 126.1 |
C26—C16—C11 | 111.65 (13) | C32—C36—H36 | 126.1 |
C17—C16—C11 | 105.60 (13) | Fe1—C36—H36 | 126.1 |
C26—C16—H16 | 108.4 | C7—N1—C6 | 114.33 (16) |
C17—C16—H16 | 108.4 | C8—N2—C5 | 114.21 (18) |
C11—C16—H16 | 108.4 | C18—N3—C19 | 114.78 (16) |
C18—C17—C20 | 116.49 (15) | C18—N3—C11 | 107.57 (13) |
C18—C17—C16 | 103.63 (14) | C19—N3—C11 | 115.88 (16) |
C20—C17—C16 | 111.41 (15) | C27—Fe1—C34 | 158.62 (13) |
C18—C17—H17 | 108.3 | C27—Fe1—C33 | 122.73 (12) |
C20—C17—H17 | 108.3 | C34—Fe1—C33 | 40.06 (13) |
C16—C17—H17 | 108.3 | C27—Fe1—C32 | 107.86 (10) |
N3—C18—C17 | 103.31 (15) | C34—Fe1—C32 | 67.33 (13) |
N3—C18—H18A | 111.1 | C33—Fe1—C32 | 40.39 (12) |
C17—C18—H18A | 111.1 | C27—Fe1—C28 | 41.46 (7) |
N3—C18—H18B | 111.1 | C34—Fe1—C28 | 158.17 (14) |
C17—C18—H18B | 111.1 | C33—Fe1—C28 | 160.99 (13) |
H18A—C18—H18B | 109.1 | C32—Fe1—C28 | 125.61 (10) |
N3—C19—H19A | 109.5 | C27—Fe1—C31 | 41.26 (7) |
N3—C19—H19B | 109.5 | C34—Fe1—C31 | 121.89 (11) |
H19A—C19—H19B | 109.5 | C33—Fe1—C31 | 105.69 (10) |
N3—C19—H19C | 109.5 | C32—Fe1—C31 | 121.51 (10) |
H19A—C19—H19C | 109.5 | C28—Fe1—C31 | 69.12 (8) |
H19B—C19—H19C | 109.5 | C27—Fe1—C35 | 159.50 (11) |
C21—C20—C25 | 118.00 (19) | C34—Fe1—C35 | 39.97 (12) |
C21—C20—C17 | 120.82 (19) | C33—Fe1—C35 | 67.43 (13) |
C25—C20—C17 | 121.02 (17) | C32—Fe1—C35 | 67.27 (12) |
C20—C21—C22 | 120.8 (2) | C28—Fe1—C35 | 123.85 (11) |
C20—C21—H21 | 119.6 | C31—Fe1—C35 | 158.63 (11) |
C22—C21—H21 | 119.6 | C27—Fe1—C36 | 123.52 (9) |
C23—C22—C21 | 120.3 (2) | C34—Fe1—C36 | 67.19 (11) |
C23—C22—H22 | 119.8 | C33—Fe1—C36 | 67.57 (11) |
C21—C22—H22 | 119.8 | C32—Fe1—C36 | 40.04 (10) |
C22—C23—C24 | 119.7 (2) | C28—Fe1—C36 | 110.11 (9) |
C22—C23—H23 | 120.2 | C31—Fe1—C36 | 158.19 (10) |
C24—C23—H23 | 120.2 | C35—Fe1—C36 | 39.97 (11) |
C23—C24—C25 | 120.2 (2) | C27—Fe1—C30 | 68.38 (8) |
C23—C24—H24 | 119.9 | C34—Fe1—C30 | 107.22 (11) |
C25—C24—H24 | 119.9 | C33—Fe1—C30 | 120.65 (11) |
C20—C25—C24 | 121.0 (2) | C32—Fe1—C30 | 156.49 (11) |
C20—C25—H25 | 119.5 | C28—Fe1—C30 | 67.93 (8) |
C24—C25—H25 | 119.5 | C31—Fe1—C30 | 40.29 (8) |
O1—C26—C27 | 121.91 (16) | C35—Fe1—C30 | 124.26 (11) |
O1—C26—C16 | 121.58 (16) | C36—Fe1—C30 | 161.12 (11) |
C27—C26—C16 | 116.49 (14) | C27—Fe1—C29 | 68.61 (8) |
C31—C27—C28 | 107.67 (16) | C34—Fe1—C29 | 122.39 (13) |
C31—C27—C26 | 124.84 (16) | C33—Fe1—C29 | 156.40 (13) |
C28—C27—C26 | 127.15 (16) | C32—Fe1—C29 | 162.17 (11) |
C31—C27—Fe1 | 70.19 (10) | C28—Fe1—C29 | 40.28 (8) |
C28—C27—Fe1 | 70.08 (10) | C31—Fe1—C29 | 68.17 (8) |
C26—C27—Fe1 | 119.97 (11) | C35—Fe1—C29 | 109.54 (11) |
C29—C28—C27 | 107.68 (17) | C36—Fe1—C29 | 126.24 (10) |
C29—C28—Fe1 | 70.77 (11) | C30—Fe1—C29 | 40.11 (8) |
C27—C28—Fe1 | 68.46 (9) | ||
C6—C1—C2—C3 | −0.8 (3) | C26—C27—Fe1—C30 | 157.15 (16) |
C1—C2—C3—C4 | −0.7 (3) | C31—C27—Fe1—C29 | 80.85 (12) |
C2—C3—C4—C5 | 1.8 (3) | C28—C27—Fe1—C29 | −37.43 (11) |
C3—C4—C5—N2 | 177.4 (2) | C26—C27—Fe1—C29 | −159.60 (16) |
C3—C4—C5—C6 | −1.3 (3) | C33—C34—Fe1—C27 | −42.9 (4) |
C2—C1—C6—N1 | −178.24 (18) | C35—C34—Fe1—C27 | −162.2 (2) |
C2—C1—C6—C5 | 1.2 (3) | C35—C34—Fe1—C33 | −119.4 (3) |
N2—C5—C6—N1 | 0.6 (3) | C33—C34—Fe1—C32 | 38.21 (18) |
C4—C5—C6—N1 | 179.28 (18) | C35—C34—Fe1—C32 | −81.2 (2) |
N2—C5—C6—C1 | −178.88 (18) | C33—C34—Fe1—C28 | 169.1 (2) |
C4—C5—C6—C1 | −0.2 (3) | C35—C34—Fe1—C28 | 49.7 (4) |
N1—C7—C8—N2 | −0.5 (3) | C33—C34—Fe1—C31 | −75.8 (2) |
C11—C7—C8—N2 | −179.79 (17) | C35—C34—Fe1—C31 | 164.81 (17) |
N1—C7—C8—C9 | −179.20 (16) | C33—C34—Fe1—C35 | 119.4 (3) |
C11—C7—C8—C9 | 1.5 (2) | C33—C34—Fe1—C36 | 81.8 (2) |
N2—C8—C9—C15 | 2.7 (3) | C35—C34—Fe1—C36 | −37.59 (19) |
C7—C8—C9—C15 | −178.7 (2) | C33—C34—Fe1—C30 | −117.43 (19) |
N2—C8—C9—C10 | −176.40 (18) | C35—C34—Fe1—C30 | 123.20 (19) |
C7—C8—C9—C10 | 2.2 (2) | C33—C34—Fe1—C29 | −158.70 (17) |
C15—C9—C10—C12 | −2.9 (3) | C35—C34—Fe1—C29 | 81.9 (2) |
C8—C9—C10—C12 | 176.24 (16) | C34—C33—Fe1—C27 | 162.85 (16) |
C15—C9—C10—C11 | 175.70 (17) | C32—C33—Fe1—C27 | −78.89 (19) |
C8—C9—C10—C11 | −5.1 (2) | C32—C33—Fe1—C34 | 118.3 (3) |
C12—C10—C11—N3 | −51.0 (2) | C34—C33—Fe1—C32 | −118.3 (3) |
C9—C10—C11—N3 | 130.52 (16) | C34—C33—Fe1—C28 | −167.5 (3) |
C12—C10—C11—C7 | −175.86 (18) | C32—C33—Fe1—C28 | −49.2 (4) |
C9—C10—C11—C7 | 5.68 (18) | C34—C33—Fe1—C31 | 121.23 (18) |
C12—C10—C11—C16 | 65.9 (2) | C32—C33—Fe1—C31 | −120.50 (17) |
C9—C10—C11—C16 | −112.52 (17) | C34—C33—Fe1—C35 | −37.32 (18) |
N1—C7—C11—N3 | 54.5 (2) | C32—C33—Fe1—C35 | 80.95 (19) |
C8—C7—C11—N3 | −126.27 (16) | C34—C33—Fe1—C36 | −80.7 (2) |
N1—C7—C11—C10 | 176.52 (17) | C32—C33—Fe1—C36 | 37.53 (17) |
C8—C7—C11—C10 | −4.21 (18) | C34—C33—Fe1—C30 | 80.2 (2) |
N1—C7—C11—C16 | −61.1 (2) | C32—C33—Fe1—C30 | −161.52 (16) |
C8—C7—C11—C16 | 118.22 (16) | C34—C33—Fe1—C29 | 50.0 (3) |
C9—C10—C12—C13 | 2.8 (3) | C32—C33—Fe1—C29 | 168.3 (2) |
C11—C10—C12—C13 | −175.51 (18) | C36—C32—Fe1—C27 | −121.22 (16) |
C10—C12—C13—C14 | −0.5 (3) | C33—C32—Fe1—C27 | 119.86 (19) |
C12—C13—C14—C15 | −1.8 (4) | C36—C32—Fe1—C34 | 81.02 (19) |
C13—C14—C15—C9 | 1.8 (3) | C33—C32—Fe1—C34 | −37.90 (18) |
C10—C9—C15—C14 | 0.6 (3) | C36—C32—Fe1—C33 | 118.9 (3) |
C8—C9—C15—C14 | −178.4 (2) | C36—C32—Fe1—C28 | −78.75 (18) |
N3—C11—C16—C26 | 111.69 (15) | C33—C32—Fe1—C28 | 162.33 (18) |
C10—C11—C16—C26 | −10.9 (2) | C36—C32—Fe1—C31 | −164.43 (14) |
C7—C11—C16—C26 | −124.01 (15) | C33—C32—Fe1—C31 | 76.6 (2) |
N3—C11—C16—C17 | −13.10 (17) | C36—C32—Fe1—C35 | 37.53 (17) |
C10—C11—C16—C17 | −135.71 (15) | C33—C32—Fe1—C35 | −81.4 (2) |
C7—C11—C16—C17 | 111.19 (16) | C33—C32—Fe1—C36 | −118.9 (3) |
C26—C16—C17—C18 | −135.03 (15) | C36—C32—Fe1—C30 | 162.1 (2) |
C11—C16—C17—C18 | −11.90 (17) | C33—C32—Fe1—C30 | 43.1 (3) |
C26—C16—C17—C20 | 98.96 (17) | C36—C32—Fe1—C29 | −45.7 (4) |
C11—C16—C17—C20 | −137.91 (15) | C33—C32—Fe1—C29 | −164.6 (3) |
C20—C17—C18—N3 | 155.72 (16) | C29—C28—Fe1—C27 | −118.92 (16) |
C16—C17—C18—N3 | 33.00 (18) | C29—C28—Fe1—C34 | 44.1 (3) |
C18—C17—C20—C21 | 129.3 (2) | C27—C28—Fe1—C34 | 163.1 (3) |
C16—C17—C20—C21 | −112.1 (2) | C29—C28—Fe1—C33 | −157.8 (3) |
C18—C17—C20—C25 | −55.5 (2) | C27—C28—Fe1—C33 | −38.9 (3) |
C16—C17—C20—C25 | 63.1 (2) | C29—C28—Fe1—C32 | 165.02 (14) |
C25—C20—C21—C22 | −2.6 (3) | C27—C28—Fe1—C32 | −76.07 (14) |
C17—C20—C21—C22 | 172.7 (2) | C29—C28—Fe1—C31 | −80.48 (13) |
C20—C21—C22—C23 | 1.5 (4) | C27—C28—Fe1—C31 | 38.44 (10) |
C21—C22—C23—C24 | 0.7 (4) | C29—C28—Fe1—C35 | 80.30 (17) |
C22—C23—C24—C25 | −1.8 (4) | C27—C28—Fe1—C35 | −160.79 (14) |
C21—C20—C25—C24 | 1.6 (3) | C29—C28—Fe1—C36 | 122.81 (14) |
C17—C20—C25—C24 | −173.73 (19) | C27—C28—Fe1—C36 | −118.28 (13) |
C23—C24—C25—C20 | 0.6 (3) | C29—C28—Fe1—C30 | −37.05 (12) |
C17—C16—C26—O1 | 23.5 (2) | C27—C28—Fe1—C30 | 81.86 (12) |
C11—C16—C26—O1 | −96.32 (18) | C27—C28—Fe1—C29 | 118.92 (16) |
C17—C16—C26—C27 | −158.23 (14) | C30—C31—Fe1—C27 | 118.71 (16) |
C11—C16—C26—C27 | 81.98 (17) | C30—C31—Fe1—C34 | −78.78 (19) |
O1—C26—C27—C31 | −1.2 (3) | C27—C31—Fe1—C34 | 162.51 (17) |
C16—C26—C27—C31 | −179.50 (15) | C30—C31—Fe1—C33 | −119.18 (17) |
O1—C26—C27—C28 | −173.65 (16) | C27—C31—Fe1—C33 | 122.10 (16) |
C16—C26—C27—C28 | 8.1 (2) | C30—C31—Fe1—C32 | −160.09 (14) |
O1—C26—C27—Fe1 | −86.89 (18) | C27—C31—Fe1—C32 | 81.19 (15) |
C16—C26—C27—Fe1 | 94.82 (15) | C30—C31—Fe1—C28 | 80.10 (12) |
C31—C27—C28—C29 | −0.24 (19) | C27—C31—Fe1—C28 | −38.62 (10) |
C26—C27—C28—C29 | 173.25 (16) | C30—C31—Fe1—C35 | −51.3 (3) |
Fe1—C27—C28—C29 | 60.17 (13) | C27—C31—Fe1—C35 | −170.0 (3) |
C31—C27—C28—Fe1 | −60.41 (12) | C30—C31—Fe1—C36 | 172.2 (2) |
C26—C27—C28—Fe1 | 113.08 (16) | C27—C31—Fe1—C36 | 53.5 (3) |
C27—C28—C29—C30 | 0.2 (2) | C27—C31—Fe1—C30 | −118.71 (16) |
Fe1—C28—C29—C30 | 58.96 (14) | C30—C31—Fe1—C29 | 36.71 (12) |
C27—C28—C29—Fe1 | −58.71 (12) | C27—C31—Fe1—C29 | −82.00 (12) |
C28—C29—C30—C31 | −0.2 (2) | C34—C35—Fe1—C27 | 161.5 (3) |
Fe1—C29—C30—C31 | 58.25 (14) | C36—C35—Fe1—C27 | 42.6 (4) |
C28—C29—C30—Fe1 | −58.40 (13) | C36—C35—Fe1—C34 | −118.9 (3) |
C29—C30—C31—C27 | 0.0 (2) | C34—C35—Fe1—C33 | 37.4 (2) |
Fe1—C30—C31—C27 | 58.86 (12) | C36—C35—Fe1—C33 | −81.5 (2) |
C29—C30—C31—Fe1 | −58.85 (14) | C34—C35—Fe1—C32 | 81.3 (2) |
C28—C27—C31—C30 | 0.15 (19) | C36—C35—Fe1—C32 | −37.59 (17) |
C26—C27—C31—C30 | −173.54 (16) | C34—C35—Fe1—C28 | −160.03 (19) |
Fe1—C27—C31—C30 | −60.19 (13) | C36—C35—Fe1—C28 | 81.04 (19) |
C28—C27—C31—Fe1 | 60.34 (11) | C34—C35—Fe1—C31 | −37.6 (4) |
C26—C27—C31—Fe1 | −113.35 (16) | C36—C35—Fe1—C31 | −156.5 (2) |
C36—C32—C33—C34 | −0.3 (3) | C34—C35—Fe1—C36 | 118.9 (3) |
Fe1—C32—C33—C34 | 59.88 (18) | C34—C35—Fe1—C30 | −75.2 (2) |
C36—C32—C33—Fe1 | −60.18 (16) | C36—C35—Fe1—C30 | 165.84 (15) |
C32—C33—C34—C35 | 0.3 (3) | C34—C35—Fe1—C29 | −117.5 (2) |
Fe1—C33—C34—C35 | 60.48 (19) | C36—C35—Fe1—C29 | 123.59 (17) |
C32—C33—C34—Fe1 | −60.15 (17) | C35—C36—Fe1—C27 | −163.49 (17) |
C33—C34—C35—C36 | −0.2 (3) | C32—C36—Fe1—C27 | 77.51 (18) |
Fe1—C34—C35—C36 | 59.97 (17) | C35—C36—Fe1—C34 | 37.6 (2) |
C33—C34—C35—Fe1 | −60.20 (18) | C32—C36—Fe1—C34 | −81.4 (2) |
C34—C35—C36—C32 | 0.0 (3) | C35—C36—Fe1—C33 | 81.1 (2) |
Fe1—C35—C36—C32 | 59.34 (16) | C32—C36—Fe1—C33 | −37.85 (19) |
C34—C35—C36—Fe1 | −59.30 (18) | C35—C36—Fe1—C32 | 119.0 (2) |
C33—C32—C36—C35 | 0.2 (3) | C35—C36—Fe1—C28 | −119.12 (18) |
Fe1—C32—C36—C35 | −59.47 (17) | C32—C36—Fe1—C28 | 121.88 (17) |
C33—C32—C36—Fe1 | 59.63 (16) | C35—C36—Fe1—C31 | 157.0 (2) |
C8—C7—N1—C6 | 2.2 (2) | C32—C36—Fe1—C31 | 38.0 (3) |
C11—C7—N1—C6 | −178.60 (15) | C32—C36—Fe1—C35 | −119.0 (2) |
C1—C6—N1—C7 | 177.24 (17) | C35—C36—Fe1—C30 | −38.7 (4) |
C5—C6—N1—C7 | −2.2 (2) | C32—C36—Fe1—C30 | −157.7 (3) |
C7—C8—N2—C5 | −1.3 (3) | C35—C36—Fe1—C29 | −76.8 (2) |
C9—C8—N2—C5 | 177.16 (18) | C32—C36—Fe1—C29 | 164.24 (16) |
C4—C5—N2—C8 | −177.52 (18) | C31—C30—Fe1—C27 | −38.48 (11) |
C6—C5—N2—C8 | 1.2 (3) | C29—C30—Fe1—C27 | 82.04 (12) |
C17—C18—N3—C19 | −174.78 (16) | C31—C30—Fe1—C34 | 119.31 (17) |
C17—C18—N3—C11 | −44.20 (18) | C29—C30—Fe1—C34 | −120.17 (17) |
C10—C11—N3—C18 | 160.03 (15) | C31—C30—Fe1—C33 | 77.70 (18) |
C7—C11—N3—C18 | −84.29 (18) | C29—C30—Fe1—C33 | −161.78 (17) |
C16—C11—N3—C18 | 35.34 (17) | C31—C30—Fe1—C32 | 46.7 (3) |
C10—C11—N3—C19 | −70.0 (2) | C29—C30—Fe1—C32 | 167.2 (2) |
C7—C11—N3—C19 | 45.7 (2) | C31—C30—Fe1—C28 | −83.31 (12) |
C16—C11—N3—C19 | 165.29 (16) | C29—C30—Fe1—C28 | 37.21 (12) |
C31—C27—Fe1—C34 | −44.4 (3) | C29—C30—Fe1—C31 | 120.52 (17) |
C28—C27—Fe1—C34 | −162.7 (3) | C31—C30—Fe1—C35 | 159.88 (15) |
C26—C27—Fe1—C34 | 75.1 (3) | C29—C30—Fe1—C35 | −79.60 (17) |
C31—C27—Fe1—C33 | −75.80 (16) | C31—C30—Fe1—C36 | −171.1 (3) |
C28—C27—Fe1—C33 | 165.92 (14) | C29—C30—Fe1—C36 | −50.5 (3) |
C26—C27—Fe1—C33 | 43.75 (19) | C31—C30—Fe1—C29 | −120.52 (17) |
C31—C27—Fe1—C32 | −117.72 (14) | C28—C29—Fe1—C27 | 38.50 (11) |
C28—C27—Fe1—C32 | 124.00 (13) | C30—C29—Fe1—C27 | −81.42 (13) |
C26—C27—Fe1—C32 | 1.83 (18) | C28—C29—Fe1—C34 | −162.14 (15) |
C31—C27—Fe1—C28 | 118.28 (15) | C30—C29—Fe1—C34 | 77.94 (17) |
C26—C27—Fe1—C28 | −122.17 (18) | C28—C29—Fe1—C33 | 162.1 (3) |
C28—C27—Fe1—C31 | −118.28 (15) | C30—C29—Fe1—C33 | 42.2 (3) |
C26—C27—Fe1—C31 | 119.55 (18) | C28—C29—Fe1—C32 | −43.3 (4) |
C31—C27—Fe1—C35 | 169.6 (3) | C30—C29—Fe1—C32 | −163.3 (3) |
C28—C27—Fe1—C35 | 51.3 (3) | C30—C29—Fe1—C28 | −119.91 (17) |
C26—C27—Fe1—C35 | −70.9 (3) | C28—C29—Fe1—C31 | 83.04 (12) |
C31—C27—Fe1—C36 | −159.01 (13) | C30—C29—Fe1—C31 | −36.88 (12) |
C28—C27—Fe1—C36 | 82.71 (14) | C28—C29—Fe1—C35 | −119.70 (14) |
C26—C27—Fe1—C36 | −39.46 (18) | C30—C29—Fe1—C35 | 120.39 (15) |
C31—C27—Fe1—C30 | 37.60 (11) | C28—C29—Fe1—C36 | −78.13 (16) |
C28—C27—Fe1—C30 | −80.68 (12) | C30—C29—Fe1—C36 | 161.96 (14) |
Cg1 is the centroid of the C20–C25 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C31—H31···N3i | 0.98 | 2.45 | 3.430 (2) | 176 |
C1—H1···Cg1ii | 0.93 | 2.83 | 3.650 (2) | 147 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C31H24N3O)] |
Mr | 575.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.1008 (4), 11.9156 (5), 21.0511 (9) |
β (°) | 90.944 (2) |
V (Å3) | 2784.11 (19) |
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 APEX2 area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26663, 7107, 4920 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.675 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.105, 1.00 |
No. of reflections | 7107 |
No. of parameters | 370 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.31 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 is the centroid of the C20–C25 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C31—H31···N3i | 0.98 | 2.45 | 3.430 (2) | 176 |
C1—H1···Cg1ii | 0.93 | 2.83 | 3.650 (2) | 147 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y, −z. |
Acknowledgements
BV and DV 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
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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 derivatives are well known to have biological activities like antitumor (Jaouen et al., 2004), antimalarial and antifungal (Biot et al., 2004), and antibacterial (Fouda et al., 2007). Against this background and in order to obtain detailed information on molecular conformations in the solid state, X-ray diffraction study of the title compound was carried out.
In the title compound (Fig. 1) the pyrrolidine ring adopts a twisted conformation with the puckering parameters q2 and ϕ and the smallest displacement asymmetric parameters, ϕ, as follows: q2 = 0.392 (2) Å, ϕ = 162.8 (3)° and Δ2(C16) = 1.84 (2)°. The indeno-quinoxaline unit is essentially planar, with a mean deviation of 0.074 (2) Å from the least-squares plane defined by the seventeen constituent atoms. The dihedral angle between the pyrrolidine ring (C11/C16–C18/N3) and the plane of indeno-quinoxaline fragment (C1–C6/N1/N2/C7–C15) is 86.3 (3)°. The Fe1···Cg2 and Fe1···Cg3 distances are 1.6461 (8) and 1.6506 (10) Å, respectively and the Cg2···Fe1···Cg3 angle is 177.91 (6)°, where Cg2 and Cg3 are the centroids of the C27–C31 and C32–C36 cyclopentadinene rings, respectively. In the crystal structure (Fig. 2), molecules are connected by weak C—H···N and C—H···π interactions (Table 1, Cg1 is the centroid of the C20–C25 phenyl ring).