metal-organic compounds
Bis(4,6-di-tert-butyl-2-{N-[4-(diethylamino)phenyl]carboximidoyl}phenolato)cobalt(II)
aDepartment of Chemistry, Vaigai College of Engineering, Madurai 625122, Tamil Nadu, India, bDepartment of Chemistry, University of Pitesti, Pitesti 11040, Romania, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dPG & Research Department of Chemistry, Chikkanna Government Arts College, Tiruppur 641 602, Tamil Nadu, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com
In the title complex, [Co(C25H35N2O)2], the cobalt(II) atom has a distorted tetrahedral geometry provided by pairs of O and N atoms. The dihedral angles between the benzene rings of the same ligand are 52.39 (9) and 34.96 (9)°. The molecular structure is stabilized by weak intramolecular C—H⋯O hydrogen bonds. The crystal packing is stabilized mainly by The structure contains a solvent-accessible void of 276 Å3 which was treated using the SQUEEZE routine from PLATON [Spek (2015). Acta Cryst. C71, 9–18]. The methyl C atoms of the tert-butyl groups are rotationally disordered, with site occupancies of 0.802 (3) and 0.548 (9) for the major components and 0.198 (3) and 0.452 (9) for the minor components.
CCDC reference: 1552570
Structure description
In our continuing work on the development of new N- and O-chelating ligands able to play a key role in the coordination of metals at the active sites of numerous metallobimolecules (Nair et al., 2006), we herein report on the synthesis and the of the title compound (Fig. 1). The cobalt(II) atom is coordinated in a distorted tetrahedral geometry by two O and two N atoms. The Co—O and Co—N bond lengths [Co1—O1 = 1.8844 (18), Co1—O2 = 1.8867 (17), Co1—N1 = 20 1.978 (2) and Co1—N2 = 1.971 (2) Å] are similar to those reported in related structures (Adam et al., 1997; Chen et al., 2014, 2015). Within the same ligand, the dihedral angles formed by the benzene rings are 52.39 (9) and 34.96 (9)°. The molecular structure is stabilized by weak C—H⋯O hydrogen bonds (Table 1). The crystal packing is mainly stabilized by van der Waals forces.
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Synthesis and crystallization
To a solution of the Schiff base (1 mmol) in 10 ml methanol was added a solution of Co(AcO)2·H2O (0.5 mmol) in 10 ml ethanol. The resulting mixture was refluxed for 4–6 h and then cooled to room temperature. The precipitate obtained was filtered, washed in ice-cold ethanol and dried in vacuo. X-ray quality crystals were grown by layering a CHCl3 solution (3 ml) of the compound with CH3CN (5 ml).
Refinement
Crystal data, data collection and structure . The methyl C atoms of the tert-butyl groups are rotationally disordered, with site occupancies of 0.802 (3) and 0.548 (9) for the major components (C12, C13, C14 and C37A, C38A, C39A), and 0.198 (3) and 0.452 (9) for the minor components (C12A, C13A, C14A and C37, C38, C39). The C—C bond lengths involving the disordered atoms were restrained to 1.50 (1) Å. SIMU, SADI and DELU restraints were also applied. The structure contains a solvent-accessible void which was treated using the SQUEEZE routine from PLATON (Spek, 2015).
details are summarized in Table 2Structural data
CCDC reference: 1552570
https://doi.org/10.1107/S2414314617007842/rz4015sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617007842/rz4015Isup2.hkl
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).[Co(C25H35N2O)2] | Z = 2 |
Mr = 818.03 | F(000) = 882 |
Triclinic, P1 | Dx = 1.075 Mg m−3 |
a = 11.9460 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.2180 (2) Å | Cell parameters from 8860 reflections |
c = 17.4340 (2) Å | θ = 2.2–22.1° |
α = 109.348 (1)° | µ = 0.38 mm−1 |
β = 96.350 (1)° | T = 295 K |
γ = 98.881 (2)° | Block, colourless |
V = 2527.33 (6) Å3 | 0.28 × 0.24 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 5894 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.045 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | θmax = 24.3°, θmin = 2.0° |
Tmin = 0.851, Tmax = 0.928 | h = −13→13 |
38553 measured reflections | k = −15→15 |
8091 independent reflections | l = −20→20 |
Refinement on F2 | 105 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0808P)2 + 0.0839P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
8091 reflections | Δρmax = 0.43 e Å−3 |
592 parameters | Δρmin = −0.36 e Å−3 |
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. All H atoms were positioned geometrically and refined as riding, with C–H = 0.93–0.97 Å, and Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms. A rotating model was used for the methyl groups. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.7275 (2) | −0.1630 (2) | 0.29792 (15) | 0.0416 (6) | |
C2 | 0.6716 (2) | −0.2748 (2) | 0.25854 (16) | 0.0491 (7) | |
C3 | 0.6434 (2) | −0.3331 (2) | 0.30879 (18) | 0.0555 (7) | |
H3 | 0.606782 | −0.406170 | 0.283027 | 0.067* | |
C4 | 0.6648 (2) | −0.2921 (2) | 0.39406 (18) | 0.0521 (7) | |
C5 | 0.7202 (2) | −0.1854 (2) | 0.43080 (17) | 0.0487 (7) | |
H5 | 0.737078 | −0.155396 | 0.488124 | 0.058* | |
C6 | 0.7527 (2) | −0.1189 (2) | 0.38531 (15) | 0.0409 (6) | |
C7 | 0.6438 (3) | −0.3258 (2) | 0.16368 (18) | 0.0656 (8) | |
C8 | 0.7551 (3) | −0.3166 (3) | 0.1273 (2) | 0.0901 (11) | |
H8A | 0.737375 | −0.351694 | 0.068397 | 0.135* | |
H8B | 0.807989 | −0.351562 | 0.149775 | 0.135* | |
H8C | 0.789287 | −0.240734 | 0.141175 | 0.135* | |
C9 | 0.5597 (3) | −0.2679 (3) | 0.1303 (2) | 0.0868 (11) | |
H9A | 0.489036 | −0.277717 | 0.150877 | 0.130* | |
H9B | 0.544591 | −0.298377 | 0.071107 | 0.130* | |
H9C | 0.592624 | −0.191108 | 0.148060 | 0.130* | |
C10 | 0.5880 (4) | −0.4482 (3) | 0.1350 (2) | 0.1087 (15) | |
H10A | 0.516180 | −0.456372 | 0.154379 | 0.163* | |
H10B | 0.638470 | −0.485652 | 0.157071 | 0.163* | |
H10C | 0.574698 | −0.479019 | 0.075846 | 0.163* | |
C11 | 0.6289 (3) | −0.3656 (2) | 0.44291 (19) | 0.0719 (7) | |
C12 | 0.5005 (4) | −0.4117 (4) | 0.4184 (3) | 0.0872 (9) | 0.802 (3) |
H12A | 0.478052 | −0.457883 | 0.448839 | 0.131* | 0.802 (3) |
H12B | 0.482410 | −0.453715 | 0.360374 | 0.131* | 0.802 (3) |
H12C | 0.459748 | −0.352622 | 0.430557 | 0.131* | 0.802 (3) |
C13 | 0.6935 (4) | −0.4590 (3) | 0.4250 (3) | 0.0826 (9) | 0.802 (3) |
H13A | 0.774718 | −0.429758 | 0.440593 | 0.124* | 0.802 (3) |
H13B | 0.675674 | −0.502009 | 0.367135 | 0.124* | 0.802 (3) |
H13C | 0.670812 | −0.504372 | 0.456029 | 0.124* | 0.802 (3) |
C14 | 0.6576 (4) | −0.3049 (3) | 0.5350 (2) | 0.0847 (9) | 0.802 (3) |
H14A | 0.630550 | −0.352960 | 0.562969 | 0.127* | 0.802 (3) |
H14B | 0.621043 | −0.242977 | 0.549303 | 0.127* | 0.802 (3) |
H14C | 0.739409 | −0.280172 | 0.551407 | 0.127* | 0.802 (3) |
C12A | 0.5553 (16) | −0.3073 (13) | 0.5019 (11) | 0.0844 (11) | 0.198 (3) |
H12D | 0.478014 | −0.321298 | 0.473154 | 0.127* | 0.198 (3) |
H12E | 0.586233 | −0.229893 | 0.522812 | 0.127* | 0.198 (3) |
H12F | 0.555289 | −0.333744 | 0.546920 | 0.127* | 0.198 (3) |
C13A | 0.7398 (10) | −0.3798 (15) | 0.4855 (11) | 0.0827 (11) | 0.198 (3) |
H13D | 0.798941 | −0.316360 | 0.496154 | 0.124* | 0.198 (3) |
H13E | 0.762664 | −0.443509 | 0.450615 | 0.124* | 0.198 (3) |
H13F | 0.728153 | −0.388602 | 0.536722 | 0.124* | 0.198 (3) |
C14A | 0.5353 (15) | −0.4650 (12) | 0.3886 (10) | 0.0848 (13) | 0.198 (3) |
H14D | 0.570244 | −0.518950 | 0.353217 | 0.127* | 0.198 (3) |
H14E | 0.481806 | −0.442259 | 0.355656 | 0.127* | 0.198 (3) |
H14F | 0.495380 | −0.495857 | 0.423132 | 0.127* | 0.198 (3) |
C15 | 0.8064 (2) | −0.0076 (2) | 0.43271 (15) | 0.0423 (6) | |
H15 | 0.820529 | 0.010026 | 0.489624 | 0.051* | |
C16 | 0.8867 (2) | 0.1774 (2) | 0.46795 (16) | 0.0456 (6) | |
C17 | 0.9717 (2) | 0.1937 (2) | 0.53267 (17) | 0.0516 (7) | |
H17 | 1.002326 | 0.134701 | 0.536498 | 0.062* | |
C18 | 1.0128 (2) | 0.2958 (2) | 0.59233 (18) | 0.0614 (8) | |
H18 | 1.070537 | 0.303851 | 0.635609 | 0.074* | |
C19 | 0.9708 (3) | 0.3870 (2) | 0.5898 (2) | 0.0684 (9) | |
C20 | 0.8859 (3) | 0.3693 (2) | 0.5225 (2) | 0.0848 (11) | |
H20 | 0.855582 | 0.428129 | 0.517882 | 0.102* | |
C21 | 0.8457 (3) | 0.2674 (2) | 0.46256 (19) | 0.0710 (9) | |
H21 | 0.790197 | 0.259023 | 0.417872 | 0.085* | |
C22 | 1.0854 (4) | 0.5023 (3) | 0.7256 (3) | 0.1123 (13) | |
H22A | 1.120568 | 0.579168 | 0.753573 | 0.135* | |
H22B | 1.146705 | 0.462398 | 0.712887 | 0.135* | |
C23 | 1.0226 (5) | 0.4633 (5) | 0.7818 (3) | 0.146 (2) | |
H23A | 0.956104 | 0.495667 | 0.789326 | 0.220* | |
H23B | 1.071830 | 0.483679 | 0.834146 | 0.220* | |
H23C | 0.998710 | 0.384988 | 0.758492 | 0.220* | |
C24 | 0.9676 (6) | 0.5846 (3) | 0.6445 (3) | 0.1307 (19) | |
H24A | 0.952787 | 0.579007 | 0.587256 | 0.157* | |
H24B | 1.025936 | 0.650219 | 0.674167 | 0.157* | |
C25 | 0.8610 (6) | 0.5962 (4) | 0.6791 (4) | 0.163 (3) | |
H25A | 0.803323 | 0.530839 | 0.651209 | 0.244* | |
H25B | 0.833988 | 0.657701 | 0.671764 | 0.244* | |
H25C | 0.876278 | 0.607672 | 0.736938 | 0.244* | |
C26 | 0.7745 (3) | 0.1623 (2) | 0.18080 (17) | 0.0545 (7) | |
C27 | 0.6898 (3) | 0.1961 (2) | 0.13590 (18) | 0.0626 (8) | |
C28 | 0.7208 (4) | 0.2304 (3) | 0.0733 (2) | 0.0753 (10) | |
H28 | 0.665658 | 0.253495 | 0.044726 | 0.090* | |
C29 | 0.8283 (3) | 0.2333 (3) | 0.0495 (2) | 0.0760 (10) | |
C30 | 0.9069 (3) | 0.1995 (3) | 0.09240 (19) | 0.0744 (9) | |
H30 | 0.979803 | 0.200811 | 0.078298 | 0.089* | |
C31 | 0.8839 (3) | 0.1624 (2) | 0.15762 (17) | 0.0588 (8) | |
C32 | 0.5673 (3) | 0.1897 (3) | 0.1547 (2) | 0.0740 (9) | |
C33 | 0.5136 (3) | 0.0718 (3) | 0.1415 (2) | 0.0919 (11) | |
H33A | 0.558636 | 0.046452 | 0.177659 | 0.138* | |
H33B | 0.511434 | 0.026557 | 0.085202 | 0.138* | |
H33C | 0.436699 | 0.068086 | 0.153190 | 0.138* | |
C34 | 0.5693 (4) | 0.2634 (3) | 0.2430 (3) | 0.1117 (14) | |
H34A | 0.614150 | 0.239439 | 0.280318 | 0.168* | |
H34B | 0.492138 | 0.259608 | 0.254116 | 0.168* | |
H34C | 0.602880 | 0.337488 | 0.250353 | 0.168* | |
C35 | 0.4890 (4) | 0.2265 (4) | 0.0968 (3) | 0.1154 (15) | |
H35A | 0.413323 | 0.221969 | 0.110867 | 0.173* | |
H35B | 0.484527 | 0.179699 | 0.040664 | 0.173* | |
H35C | 0.520294 | 0.300729 | 0.103026 | 0.173* | |
C36 | 0.8494 (4) | 0.2657 (3) | −0.0253 (2) | 0.1072 (11) | |
C37 | 0.7516 (10) | 0.191 (2) | −0.0954 (14) | 0.124 (2) | 0.452 (9) |
H37A | 0.759247 | 0.206911 | −0.144653 | 0.185* | 0.452 (9) |
H37B | 0.678862 | 0.203175 | −0.079981 | 0.185* | 0.452 (9) |
H37C | 0.755826 | 0.115710 | −0.105485 | 0.185* | 0.452 (9) |
C38 | 0.8413 (13) | 0.3803 (8) | −0.0184 (10) | 0.1228 (16) | 0.452 (9) |
H38A | 0.836302 | 0.385919 | −0.072099 | 0.184* | 0.452 (9) |
H38B | 0.908460 | 0.430343 | 0.017311 | 0.184* | 0.452 (9) |
H38C | 0.773976 | 0.397965 | 0.004055 | 0.184* | 0.452 (9) |
C39 | 0.9580 (8) | 0.2355 (12) | −0.0555 (7) | 0.1231 (16) | 0.452 (9) |
H39A | 0.969990 | 0.260469 | −0.100365 | 0.185* | 0.452 (9) |
H39B | 0.950375 | 0.157432 | −0.074110 | 0.185* | 0.452 (9) |
H39C | 1.022413 | 0.269504 | −0.011278 | 0.185* | 0.452 (9) |
C37A | 0.7884 (10) | 0.1753 (17) | −0.1055 (12) | 0.126 (2) | 0.548 (9) |
H37D | 0.790728 | 0.202322 | −0.150234 | 0.190* | 0.548 (9) |
H37E | 0.709729 | 0.152283 | −0.101369 | 0.190* | 0.548 (9) |
H37F | 0.826119 | 0.114247 | −0.115670 | 0.190* | 0.548 (9) |
C38A | 0.7892 (11) | 0.3676 (8) | −0.0172 (8) | 0.1213 (18) | 0.548 (9) |
H38D | 0.801540 | 0.393020 | −0.061710 | 0.182* | 0.548 (9) |
H38E | 0.821645 | 0.425441 | 0.034500 | 0.182* | 0.548 (9) |
H38F | 0.708090 | 0.345483 | −0.019407 | 0.182* | 0.548 (9) |
C39A | 0.9775 (8) | 0.3155 (10) | −0.0167 (7) | 0.1234 (15) | 0.548 (9) |
H39D | 1.021770 | 0.259587 | −0.021934 | 0.185* | 0.548 (9) |
H39E | 1.003185 | 0.372552 | 0.036315 | 0.185* | 0.548 (9) |
H39F | 0.987462 | 0.345512 | −0.059312 | 0.185* | 0.548 (9) |
C40 | 0.9729 (3) | 0.1215 (2) | 0.19182 (17) | 0.0596 (8) | |
H40 | 1.042064 | 0.129469 | 0.172599 | 0.072* | |
C41 | 1.0694 (2) | 0.0376 (2) | 0.27158 (16) | 0.0504 (7) | |
C42 | 1.0537 (2) | −0.0517 (2) | 0.29725 (18) | 0.0581 (7) | |
H42 | 0.979620 | −0.083946 | 0.299053 | 0.070* | |
C43 | 1.1444 (2) | −0.0933 (3) | 0.31992 (18) | 0.0614 (8) | |
H43 | 1.130510 | −0.153533 | 0.336436 | 0.074* | |
C44 | 1.2574 (2) | −0.0476 (3) | 0.31887 (17) | 0.0596 (8) | |
C45 | 1.2722 (3) | 0.0442 (2) | 0.29534 (19) | 0.0651 (8) | |
H45 | 1.346297 | 0.078122 | 0.294935 | 0.078* | |
C46 | 1.1813 (2) | 0.0855 (2) | 0.27293 (18) | 0.0605 (8) | |
H46 | 1.194956 | 0.147235 | 0.258252 | 0.073* | |
C47 | 1.4628 (3) | −0.0539 (3) | 0.3249 (3) | 0.0932 (12) | |
H47A | 1.454860 | −0.037022 | 0.274778 | 0.112* | |
H47B | 1.504118 | −0.113325 | 0.316198 | 0.112* | |
C48 | 1.5312 (3) | 0.0439 (4) | 0.3937 (3) | 0.139 (2) | |
H48A | 1.487210 | 0.100432 | 0.406766 | 0.209* | |
H48B | 1.600936 | 0.069923 | 0.377348 | 0.209* | |
H48C | 1.549728 | 0.024581 | 0.441314 | 0.209* | |
C49 | 1.3332 (3) | −0.1838 (3) | 0.3668 (2) | 0.0879 (10) | |
H49A | 1.272892 | −0.178574 | 0.400026 | 0.105* | |
H49B | 1.403659 | −0.181647 | 0.401392 | 0.105* | |
C50 | 1.3027 (4) | −0.2902 (3) | 0.2973 (3) | 0.1095 (13) | |
H50A | 1.233502 | −0.292744 | 0.262377 | 0.164* | |
H50B | 1.290666 | −0.348637 | 0.318528 | 0.164* | |
H50C | 1.364097 | −0.298037 | 0.266006 | 0.164* | |
N1 | 0.83819 (17) | 0.07252 (16) | 0.40685 (12) | 0.0425 (5) | |
N2 | 0.96972 (19) | 0.07446 (18) | 0.24633 (13) | 0.0509 (6) | |
N3 | 1.0126 (3) | 0.4891 (2) | 0.64881 (19) | 0.0967 (10) | |
N4 | 1.3492 (2) | −0.0897 (2) | 0.34047 (19) | 0.0805 (8) | |
O1 | 0.74859 (17) | 0.13208 (15) | 0.24188 (12) | 0.0600 (5) | |
O2 | 0.75399 (15) | −0.10400 (14) | 0.25273 (11) | 0.0515 (5) | |
CO1 | 0.82532 (3) | 0.04522 (3) | 0.28727 (2) | 0.04779 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0400 (14) | 0.0473 (15) | 0.0432 (15) | 0.0107 (12) | 0.0066 (12) | 0.0226 (13) |
C2 | 0.0516 (16) | 0.0493 (16) | 0.0465 (16) | 0.0101 (13) | 0.0042 (13) | 0.0185 (14) |
C3 | 0.0653 (18) | 0.0441 (16) | 0.0550 (19) | 0.0027 (13) | 0.0051 (14) | 0.0203 (14) |
C4 | 0.0565 (17) | 0.0516 (17) | 0.0545 (18) | 0.0089 (13) | 0.0108 (14) | 0.0274 (15) |
C5 | 0.0573 (17) | 0.0499 (16) | 0.0425 (15) | 0.0098 (13) | 0.0081 (13) | 0.0218 (13) |
C6 | 0.0424 (14) | 0.0446 (15) | 0.0404 (15) | 0.0102 (11) | 0.0058 (11) | 0.0211 (13) |
C7 | 0.089 (2) | 0.0531 (18) | 0.0467 (18) | 0.0040 (16) | 0.0022 (16) | 0.0155 (15) |
C8 | 0.118 (3) | 0.091 (3) | 0.062 (2) | 0.030 (2) | 0.034 (2) | 0.019 (2) |
C9 | 0.092 (3) | 0.101 (3) | 0.056 (2) | 0.008 (2) | −0.0154 (18) | 0.027 (2) |
C10 | 0.168 (4) | 0.069 (2) | 0.055 (2) | −0.019 (2) | −0.003 (2) | 0.0048 (19) |
C11 | 0.0978 (17) | 0.0614 (16) | 0.0729 (15) | 0.0074 (12) | 0.0216 (14) | 0.0469 (14) |
C12 | 0.0994 (17) | 0.083 (2) | 0.0907 (19) | 0.0038 (14) | 0.0222 (16) | 0.0503 (17) |
C13 | 0.110 (2) | 0.0690 (17) | 0.0847 (19) | 0.0148 (14) | 0.0173 (17) | 0.0495 (15) |
C14 | 0.114 (2) | 0.0785 (19) | 0.0745 (15) | 0.0078 (16) | 0.0229 (15) | 0.0478 (14) |
C12A | 0.105 (2) | 0.080 (2) | 0.081 (2) | 0.0084 (17) | 0.0287 (17) | 0.0464 (19) |
C13A | 0.110 (2) | 0.074 (2) | 0.080 (2) | 0.0142 (17) | 0.0164 (17) | 0.0509 (18) |
C14A | 0.103 (2) | 0.074 (2) | 0.087 (2) | 0.0041 (17) | 0.0185 (19) | 0.0468 (19) |
C15 | 0.0431 (14) | 0.0513 (16) | 0.0349 (14) | 0.0113 (12) | 0.0057 (11) | 0.0178 (13) |
C16 | 0.0507 (16) | 0.0426 (15) | 0.0435 (15) | 0.0036 (12) | 0.0074 (13) | 0.0179 (13) |
C17 | 0.0483 (16) | 0.0502 (17) | 0.0545 (18) | 0.0098 (13) | 0.0043 (14) | 0.0179 (15) |
C18 | 0.0570 (18) | 0.065 (2) | 0.0527 (18) | 0.0050 (15) | −0.0037 (14) | 0.0162 (16) |
C19 | 0.086 (2) | 0.0522 (19) | 0.059 (2) | 0.0042 (16) | 0.0000 (18) | 0.0173 (16) |
C20 | 0.131 (3) | 0.0429 (18) | 0.074 (2) | 0.0189 (19) | −0.011 (2) | 0.0210 (18) |
C21 | 0.097 (2) | 0.0518 (19) | 0.0578 (19) | 0.0114 (17) | −0.0149 (17) | 0.0221 (16) |
C22 | 0.118 (3) | 0.082 (3) | 0.094 (2) | 0.016 (2) | −0.0260 (19) | −0.009 (2) |
C23 | 0.174 (5) | 0.185 (5) | 0.077 (3) | 0.078 (4) | 0.004 (3) | 0.030 (3) |
C24 | 0.204 (6) | 0.058 (3) | 0.098 (4) | 0.003 (3) | −0.020 (4) | 0.012 (2) |
C25 | 0.217 (7) | 0.110 (4) | 0.158 (6) | 0.076 (4) | −0.004 (5) | 0.035 (4) |
C26 | 0.081 (2) | 0.0424 (15) | 0.0418 (16) | 0.0072 (14) | 0.0040 (15) | 0.0211 (13) |
C27 | 0.093 (2) | 0.0466 (17) | 0.0488 (17) | 0.0129 (15) | −0.0014 (16) | 0.0223 (15) |
C28 | 0.111 (3) | 0.061 (2) | 0.056 (2) | 0.0119 (19) | −0.006 (2) | 0.0320 (17) |
C29 | 0.108 (3) | 0.073 (2) | 0.0515 (19) | 0.005 (2) | 0.0001 (19) | 0.0381 (18) |
C30 | 0.088 (2) | 0.084 (2) | 0.060 (2) | 0.0049 (19) | 0.0132 (18) | 0.0426 (19) |
C31 | 0.075 (2) | 0.0591 (18) | 0.0475 (17) | 0.0064 (15) | 0.0057 (15) | 0.0300 (15) |
C32 | 0.090 (3) | 0.068 (2) | 0.075 (2) | 0.0286 (18) | 0.0062 (19) | 0.0353 (19) |
C33 | 0.091 (3) | 0.093 (3) | 0.099 (3) | 0.010 (2) | 0.011 (2) | 0.048 (2) |
C34 | 0.133 (4) | 0.106 (3) | 0.103 (3) | 0.059 (3) | 0.025 (3) | 0.029 (3) |
C35 | 0.112 (3) | 0.127 (4) | 0.133 (4) | 0.040 (3) | −0.003 (3) | 0.081 (3) |
C36 | 0.162 (3) | 0.114 (2) | 0.0623 (18) | 0.015 (2) | 0.019 (2) | 0.0590 (18) |
C37 | 0.178 (4) | 0.143 (5) | 0.050 (5) | 0.035 (6) | 0.019 (6) | 0.035 (3) |
C38 | 0.172 (4) | 0.124 (3) | 0.109 (3) | 0.014 (3) | 0.042 (3) | 0.090 (3) |
C39 | 0.170 (3) | 0.132 (3) | 0.104 (4) | 0.017 (3) | 0.046 (3) | 0.089 (3) |
C37A | 0.184 (5) | 0.145 (5) | 0.054 (4) | 0.038 (6) | 0.025 (6) | 0.037 (2) |
C38A | 0.171 (4) | 0.122 (3) | 0.109 (3) | 0.014 (3) | 0.041 (4) | 0.091 (3) |
C39A | 0.170 (3) | 0.129 (3) | 0.107 (3) | 0.015 (3) | 0.043 (3) | 0.089 (3) |
C40 | 0.0631 (19) | 0.0670 (19) | 0.0467 (17) | 0.0008 (15) | 0.0099 (14) | 0.0230 (16) |
C41 | 0.0524 (17) | 0.0573 (17) | 0.0428 (15) | 0.0101 (14) | 0.0112 (13) | 0.0192 (14) |
C42 | 0.0491 (17) | 0.076 (2) | 0.0617 (19) | 0.0145 (15) | 0.0160 (14) | 0.0374 (17) |
C43 | 0.0580 (19) | 0.078 (2) | 0.0628 (19) | 0.0206 (16) | 0.0171 (15) | 0.0385 (17) |
C44 | 0.0548 (19) | 0.078 (2) | 0.0507 (18) | 0.0221 (16) | 0.0126 (14) | 0.0236 (16) |
C45 | 0.0477 (17) | 0.071 (2) | 0.072 (2) | 0.0048 (15) | 0.0116 (15) | 0.0218 (18) |
C46 | 0.0601 (19) | 0.0571 (18) | 0.064 (2) | 0.0071 (15) | 0.0168 (15) | 0.0215 (16) |
C47 | 0.0572 (18) | 0.106 (3) | 0.118 (3) | 0.030 (2) | 0.022 (2) | 0.033 (3) |
C48 | 0.072 (3) | 0.125 (4) | 0.185 (5) | 0.026 (3) | −0.010 (3) | 0.016 (4) |
C49 | 0.076 (2) | 0.120 (3) | 0.088 (2) | 0.043 (2) | 0.014 (2) | 0.0536 (19) |
C50 | 0.109 (3) | 0.103 (3) | 0.127 (3) | 0.033 (3) | 0.019 (3) | 0.050 (2) |
N1 | 0.0425 (12) | 0.0460 (12) | 0.0436 (12) | 0.0081 (10) | 0.0058 (10) | 0.0227 (11) |
N2 | 0.0563 (14) | 0.0540 (14) | 0.0453 (13) | 0.0077 (11) | 0.0082 (11) | 0.0232 (12) |
N3 | 0.127 (3) | 0.0534 (17) | 0.0806 (19) | 0.0029 (17) | −0.0119 (16) | 0.0025 (16) |
N4 | 0.0546 (14) | 0.095 (2) | 0.098 (2) | 0.0249 (14) | 0.0105 (14) | 0.0391 (18) |
O1 | 0.0760 (13) | 0.0679 (13) | 0.0530 (12) | 0.0266 (10) | 0.0176 (10) | 0.0362 (10) |
O2 | 0.0610 (11) | 0.0532 (11) | 0.0426 (10) | 0.0054 (9) | 0.0069 (9) | 0.0236 (9) |
CO1 | 0.0559 (3) | 0.0516 (3) | 0.0434 (2) | 0.01044 (17) | 0.00958 (17) | 0.02650 (19) |
C1—O2 | 1.309 (3) | C26—C27 | 1.426 (4) |
C1—C6 | 1.417 (3) | C27—C28 | 1.379 (4) |
C1—C2 | 1.422 (3) | C27—C32 | 1.530 (5) |
C2—C3 | 1.381 (4) | C28—C29 | 1.391 (5) |
C2—C7 | 1.540 (4) | C28—H28 | 0.9300 |
C3—C4 | 1.381 (4) | C29—C30 | 1.355 (4) |
C3—H3 | 0.9300 | C29—C36 | 1.535 (5) |
C4—C5 | 1.362 (4) | C30—C31 | 1.417 (4) |
C4—C11 | 1.534 (4) | C30—H30 | 0.9300 |
C5—C6 | 1.406 (3) | C31—C40 | 1.424 (4) |
C5—H5 | 0.9300 | C32—C34 | 1.520 (5) |
C6—C15 | 1.430 (3) | C32—C33 | 1.522 (4) |
C7—C9 | 1.529 (4) | C32—C35 | 1.545 (5) |
C7—C10 | 1.540 (4) | C33—H33A | 0.9600 |
C7—C8 | 1.540 (5) | C33—H33B | 0.9600 |
C8—H8A | 0.9600 | C33—H33C | 0.9600 |
C8—H8B | 0.9600 | C34—H34A | 0.9600 |
C8—H8C | 0.9600 | C34—H34B | 0.9600 |
C9—H9A | 0.9600 | C34—H34C | 0.9600 |
C9—H9B | 0.9600 | C35—H35A | 0.9600 |
C9—H9C | 0.9600 | C35—H35B | 0.9600 |
C10—H10A | 0.9600 | C35—H35C | 0.9600 |
C10—H10B | 0.9600 | C36—C38 | 1.498 (7) |
C10—H10C | 0.9600 | C36—C39 | 1.514 (6) |
C11—C14 | 1.510 (4) | C36—C37A | 1.522 (12) |
C11—C13A | 1.515 (8) | C36—C37 | 1.538 (8) |
C11—C12 | 1.517 (4) | C36—C39A | 1.540 (10) |
C11—C12A | 1.518 (8) | C36—C38A | 1.595 (11) |
C11—C13 | 1.521 (4) | C37—H37A | 0.9600 |
C11—C14A | 1.536 (8) | C37—H37B | 0.9600 |
C12—H12A | 0.9600 | C37—H37C | 0.9600 |
C12—H12B | 0.9600 | C38—H38A | 0.9600 |
C12—H12C | 0.9600 | C38—H38B | 0.9600 |
C13—H13A | 0.9600 | C38—H38C | 0.9600 |
C13—H13B | 0.9600 | C39—H39A | 0.9600 |
C13—H13C | 0.9600 | C39—H39B | 0.9600 |
C14—H14A | 0.9600 | C39—H39C | 0.9600 |
C14—H14B | 0.9600 | C37A—H37D | 0.9600 |
C14—H14C | 0.9600 | C37A—H37E | 0.9600 |
C12A—H12D | 0.9600 | C37A—H37F | 0.9600 |
C12A—H12E | 0.9600 | C38A—H38D | 0.9600 |
C12A—H12F | 0.9600 | C38A—H38E | 0.9600 |
C13A—H13D | 0.9600 | C38A—H38F | 0.9600 |
C13A—H13E | 0.9600 | C39A—H39D | 0.9600 |
C13A—H13F | 0.9600 | C39A—H39E | 0.9600 |
C14A—H14D | 0.9600 | C39A—H39F | 0.9600 |
C14A—H14E | 0.9600 | C40—N2 | 1.297 (3) |
C14A—H14F | 0.9600 | C40—H40 | 0.9300 |
C15—N1 | 1.303 (3) | C41—C46 | 1.383 (4) |
C15—H15 | 0.9300 | C41—C42 | 1.388 (4) |
C16—C17 | 1.367 (4) | C41—N2 | 1.434 (3) |
C16—C21 | 1.381 (4) | C42—C43 | 1.366 (4) |
C16—N1 | 1.425 (3) | C42—H42 | 0.9300 |
C17—C18 | 1.377 (4) | C43—C44 | 1.396 (4) |
C17—H17 | 0.9300 | C43—H43 | 0.9300 |
C18—C19 | 1.387 (4) | C44—N4 | 1.374 (4) |
C18—H18 | 0.9300 | C44—C45 | 1.397 (4) |
C19—N3 | 1.374 (4) | C45—C46 | 1.364 (4) |
C19—C20 | 1.394 (4) | C45—H45 | 0.9300 |
C20—C21 | 1.375 (4) | C46—H46 | 0.9300 |
C20—H20 | 0.9300 | C47—N4 | 1.452 (4) |
C21—H21 | 0.9300 | C47—C48 | 1.485 (5) |
C22—N3 | 1.457 (5) | C47—H47A | 0.9700 |
C22—C23 | 1.472 (7) | C47—H47B | 0.9700 |
C22—H22A | 0.9700 | C48—H48A | 0.9600 |
C22—H22B | 0.9700 | C48—H48B | 0.9600 |
C23—H23A | 0.9600 | C48—H48C | 0.9600 |
C23—H23B | 0.9600 | C49—N4 | 1.456 (4) |
C23—H23C | 0.9600 | C49—C50 | 1.480 (5) |
C24—N3 | 1.467 (5) | C49—H49A | 0.9700 |
C24—C25 | 1.476 (7) | C49—H49B | 0.9700 |
C24—H24A | 0.9700 | C50—H50A | 0.9600 |
C24—H24B | 0.9700 | C50—H50B | 0.9600 |
C25—H25A | 0.9600 | C50—H50C | 0.9600 |
C25—H25B | 0.9600 | N1—CO1 | 1.978 (2) |
C25—H25C | 0.9600 | N2—CO1 | 1.971 (2) |
C26—O1 | 1.306 (3) | O1—CO1 | 1.8844 (18) |
C26—C31 | 1.409 (4) | O2—CO1 | 1.8867 (17) |
O2—C1—C6 | 122.0 (2) | C30—C29—C36 | 123.9 (4) |
O2—C1—C2 | 119.3 (2) | C28—C29—C36 | 119.9 (3) |
C6—C1—C2 | 118.6 (2) | C29—C30—C31 | 123.4 (3) |
C3—C2—C1 | 117.2 (2) | C29—C30—H30 | 118.3 |
C3—C2—C7 | 122.7 (2) | C31—C30—H30 | 118.3 |
C1—C2—C7 | 120.1 (2) | C26—C31—C30 | 118.9 (3) |
C2—C3—C4 | 125.6 (3) | C26—C31—C40 | 124.8 (2) |
C2—C3—H3 | 117.2 | C30—C31—C40 | 116.3 (3) |
C4—C3—H3 | 117.2 | C34—C32—C33 | 110.3 (3) |
C5—C4—C3 | 116.5 (2) | C34—C32—C27 | 109.9 (3) |
C5—C4—C11 | 123.0 (3) | C33—C32—C27 | 109.7 (3) |
C3—C4—C11 | 120.5 (3) | C34—C32—C35 | 108.0 (3) |
C4—C5—C6 | 122.5 (2) | C33—C32—C35 | 106.8 (3) |
C4—C5—H5 | 118.8 | C27—C32—C35 | 112.0 (3) |
C6—C5—H5 | 118.8 | C32—C33—H33A | 109.5 |
C5—C6—C1 | 119.6 (2) | C32—C33—H33B | 109.5 |
C5—C6—C15 | 115.9 (2) | H33A—C33—H33B | 109.5 |
C1—C6—C15 | 124.4 (2) | C32—C33—H33C | 109.5 |
C9—C7—C2 | 109.8 (2) | H33A—C33—H33C | 109.5 |
C9—C7—C10 | 108.2 (3) | H33B—C33—H33C | 109.5 |
C2—C7—C10 | 110.9 (2) | C32—C34—H34A | 109.5 |
C9—C7—C8 | 110.2 (3) | C32—C34—H34B | 109.5 |
C2—C7—C8 | 110.1 (3) | H34A—C34—H34B | 109.5 |
C10—C7—C8 | 107.6 (3) | C32—C34—H34C | 109.5 |
C7—C8—H8A | 109.5 | H34A—C34—H34C | 109.5 |
C7—C8—H8B | 109.5 | H34B—C34—H34C | 109.5 |
H8A—C8—H8B | 109.5 | C32—C35—H35A | 109.5 |
C7—C8—H8C | 109.5 | C32—C35—H35B | 109.5 |
H8A—C8—H8C | 109.5 | H35A—C35—H35B | 109.5 |
H8B—C8—H8C | 109.5 | C32—C35—H35C | 109.5 |
C7—C9—H9A | 109.5 | H35A—C35—H35C | 109.5 |
C7—C9—H9B | 109.5 | H35B—C35—H35C | 109.5 |
H9A—C9—H9B | 109.5 | C38—C36—C39 | 111.9 (7) |
C7—C9—H9C | 109.5 | C38—C36—C29 | 116.8 (6) |
H9A—C9—H9C | 109.5 | C39—C36—C29 | 112.2 (5) |
H9B—C9—H9C | 109.5 | C37A—C36—C29 | 111.0 (12) |
C7—C10—H10A | 109.5 | C38—C36—C37 | 105.6 (14) |
C7—C10—H10B | 109.5 | C39—C36—C37 | 104.3 (6) |
H10A—C10—H10B | 109.5 | C29—C36—C37 | 104.8 (14) |
C7—C10—H10C | 109.5 | C37A—C36—C39A | 119.1 (8) |
H10A—C10—H10C | 109.5 | C29—C36—C39A | 110.5 (4) |
H10B—C10—H10C | 109.5 | C37A—C36—C38A | 106.4 (10) |
C14—C11—C12 | 109.2 (3) | C29—C36—C38A | 105.7 (5) |
C13A—C11—C12A | 113.9 (11) | C39A—C36—C38A | 102.9 (6) |
C14—C11—C13 | 106.2 (3) | C36—C37—H37A | 109.5 |
C12—C11—C13 | 109.5 (3) | C36—C37—H37B | 109.5 |
C14—C11—C4 | 112.3 (3) | H37A—C37—H37B | 109.5 |
C13A—C11—C4 | 105.9 (6) | C36—C37—H37C | 109.5 |
C12—C11—C4 | 109.5 (3) | H37A—C37—H37C | 109.5 |
C12A—C11—C4 | 106.7 (7) | H37B—C37—H37C | 109.5 |
C13—C11—C4 | 110.0 (3) | C36—C38—H38A | 109.5 |
C13A—C11—C14A | 121.2 (10) | C36—C38—H38B | 109.5 |
C12A—C11—C14A | 98.0 (11) | H38A—C38—H38B | 109.5 |
C4—C11—C14A | 110.4 (7) | C36—C38—H38C | 109.5 |
C11—C12—H12A | 109.5 | H38A—C38—H38C | 109.5 |
C11—C12—H12B | 109.5 | H38B—C38—H38C | 109.5 |
H12A—C12—H12B | 109.5 | C36—C39—H39A | 109.5 |
C11—C12—H12C | 109.5 | C36—C39—H39B | 109.5 |
H12A—C12—H12C | 109.5 | H39A—C39—H39B | 109.5 |
H12B—C12—H12C | 109.5 | C36—C39—H39C | 109.5 |
C11—C13—H13A | 109.5 | H39A—C39—H39C | 109.5 |
C11—C13—H13B | 109.5 | H39B—C39—H39C | 109.5 |
H13A—C13—H13B | 109.5 | C36—C37A—H37D | 109.5 |
C11—C13—H13C | 109.5 | C36—C37A—H37E | 109.5 |
H13A—C13—H13C | 109.5 | H37D—C37A—H37E | 109.5 |
H13B—C13—H13C | 109.5 | C36—C37A—H37F | 109.5 |
C11—C14—H14A | 109.5 | H37D—C37A—H37F | 109.5 |
C11—C14—H14B | 109.5 | H37E—C37A—H37F | 109.5 |
H14A—C14—H14B | 109.5 | C36—C38A—H38D | 109.5 |
C11—C14—H14C | 109.5 | C36—C38A—H38E | 109.5 |
H14A—C14—H14C | 109.5 | H38D—C38A—H38E | 109.5 |
H14B—C14—H14C | 109.5 | C36—C38A—H38F | 109.5 |
C11—C12A—H12D | 109.5 | H38D—C38A—H38F | 109.5 |
C11—C12A—H12E | 109.5 | H38E—C38A—H38F | 109.5 |
H12D—C12A—H12E | 109.5 | C36—C39A—H39D | 109.5 |
C11—C12A—H12F | 109.5 | C36—C39A—H39E | 109.5 |
H12D—C12A—H12F | 109.5 | H39D—C39A—H39E | 109.5 |
H12E—C12A—H12F | 109.5 | C36—C39A—H39F | 109.5 |
C11—C13A—H13D | 109.5 | H39D—C39A—H39F | 109.5 |
C11—C13A—H13E | 109.5 | H39E—C39A—H39F | 109.5 |
H13D—C13A—H13E | 109.5 | N2—C40—C31 | 128.3 (3) |
C11—C13A—H13F | 109.5 | N2—C40—H40 | 115.8 |
H13D—C13A—H13F | 109.5 | C31—C40—H40 | 115.8 |
H13E—C13A—H13F | 109.5 | C46—C41—C42 | 117.2 (3) |
C11—C14A—H14D | 109.5 | C46—C41—N2 | 124.4 (2) |
C11—C14A—H14E | 109.5 | C42—C41—N2 | 118.4 (2) |
H14D—C14A—H14E | 109.5 | C43—C42—C41 | 121.7 (3) |
C11—C14A—H14F | 109.5 | C43—C42—H42 | 119.2 |
H14D—C14A—H14F | 109.5 | C41—C42—H42 | 119.2 |
H14E—C14A—H14F | 109.5 | C42—C43—C44 | 121.5 (3) |
N1—C15—C6 | 128.7 (2) | C42—C43—H43 | 119.2 |
N1—C15—H15 | 115.7 | C44—C43—H43 | 119.2 |
C6—C15—H15 | 115.7 | N4—C44—C43 | 122.1 (3) |
C17—C16—C21 | 117.9 (3) | N4—C44—C45 | 121.7 (3) |
C17—C16—N1 | 123.2 (2) | C43—C44—C45 | 116.2 (3) |
C21—C16—N1 | 118.9 (2) | C46—C45—C44 | 121.9 (3) |
C16—C17—C18 | 121.3 (3) | C46—C45—H45 | 119.0 |
C16—C17—H17 | 119.3 | C44—C45—H45 | 119.0 |
C18—C17—H17 | 119.3 | C45—C46—C41 | 121.4 (3) |
C17—C18—C19 | 122.0 (3) | C45—C46—H46 | 119.3 |
C17—C18—H18 | 119.0 | C41—C46—H46 | 119.3 |
C19—C18—H18 | 119.0 | N4—C47—C48 | 112.9 (3) |
N3—C19—C18 | 122.1 (3) | N4—C47—H47A | 109.0 |
N3—C19—C20 | 122.0 (3) | C48—C47—H47A | 109.0 |
C18—C19—C20 | 115.9 (3) | N4—C47—H47B | 109.0 |
C21—C20—C19 | 122.0 (3) | C48—C47—H47B | 109.0 |
C21—C20—H20 | 119.0 | H47A—C47—H47B | 107.8 |
C19—C20—H20 | 119.0 | C47—C48—H48A | 109.5 |
C20—C21—C16 | 120.8 (3) | C47—C48—H48B | 109.5 |
C20—C21—H21 | 119.6 | H48A—C48—H48B | 109.5 |
C16—C21—H21 | 119.6 | C47—C48—H48C | 109.5 |
N3—C22—C23 | 113.3 (4) | H48A—C48—H48C | 109.5 |
N3—C22—H22A | 108.9 | H48B—C48—H48C | 109.5 |
C23—C22—H22A | 108.9 | N4—C49—C50 | 113.5 (3) |
N3—C22—H22B | 108.9 | N4—C49—H49A | 108.9 |
C23—C22—H22B | 108.9 | C50—C49—H49A | 108.9 |
H22A—C22—H22B | 107.7 | N4—C49—H49B | 108.9 |
C22—C23—H23A | 109.5 | C50—C49—H49B | 108.9 |
C22—C23—H23B | 109.5 | H49A—C49—H49B | 107.7 |
H23A—C23—H23B | 109.5 | C49—C50—H50A | 109.5 |
C22—C23—H23C | 109.5 | C49—C50—H50B | 109.5 |
H23A—C23—H23C | 109.5 | H50A—C50—H50B | 109.5 |
H23B—C23—H23C | 109.5 | C49—C50—H50C | 109.5 |
N3—C24—C25 | 113.7 (4) | H50A—C50—H50C | 109.5 |
N3—C24—H24A | 108.8 | H50B—C50—H50C | 109.5 |
C25—C24—H24A | 108.8 | C15—N1—C16 | 117.2 (2) |
N3—C24—H24B | 108.8 | C15—N1—CO1 | 120.36 (17) |
C25—C24—H24B | 108.8 | C16—N1—CO1 | 122.34 (15) |
H24A—C24—H24B | 107.7 | C40—N2—C41 | 119.3 (2) |
C24—C25—H25A | 109.5 | C40—N2—CO1 | 119.7 (2) |
C24—C25—H25B | 109.5 | C41—N2—CO1 | 120.85 (16) |
H25A—C25—H25B | 109.5 | C19—N3—C22 | 120.7 (3) |
C24—C25—H25C | 109.5 | C19—N3—C24 | 121.2 (3) |
H25A—C25—H25C | 109.5 | C22—N3—C24 | 117.1 (3) |
H25B—C25—H25C | 109.5 | C44—N4—C47 | 121.0 (3) |
O1—C26—C31 | 122.1 (3) | C44—N4—C49 | 121.4 (3) |
O1—C26—C27 | 119.2 (3) | C47—N4—C49 | 116.9 (3) |
C31—C26—C27 | 118.8 (3) | C26—O1—CO1 | 126.01 (19) |
C28—C27—C26 | 117.8 (3) | C1—O2—CO1 | 128.76 (16) |
C28—C27—C32 | 121.4 (3) | O1—CO1—O2 | 116.00 (8) |
C26—C27—C32 | 120.7 (3) | O1—CO1—N2 | 95.76 (8) |
C27—C28—C29 | 125.1 (3) | O2—CO1—N2 | 114.94 (8) |
C27—C28—H28 | 117.5 | O1—CO1—N1 | 119.33 (8) |
C29—C28—H28 | 117.5 | O2—CO1—N1 | 95.57 (8) |
C30—C29—C28 | 116.1 (3) | N2—CO1—N1 | 116.77 (9) |
O2—C1—C2—C3 | −178.8 (2) | C26—C27—C32—C33 | −59.5 (4) |
C6—C1—C2—C3 | 1.1 (4) | C28—C27—C32—C35 | −0.5 (4) |
O2—C1—C2—C7 | 0.7 (4) | C26—C27—C32—C35 | −178.0 (3) |
C6—C1—C2—C7 | −179.4 (2) | C30—C29—C36—C38 | −120.1 (8) |
C1—C2—C3—C4 | 0.0 (4) | C28—C29—C36—C38 | 64.3 (9) |
C7—C2—C3—C4 | −179.4 (3) | C30—C29—C36—C39 | 10.9 (8) |
C2—C3—C4—C5 | −1.1 (4) | C28—C29—C36—C39 | −164.7 (7) |
C2—C3—C4—C11 | 179.9 (3) | C30—C29—C36—C37A | 103.3 (7) |
C3—C4—C5—C6 | 1.0 (4) | C28—C29—C36—C37A | −72.3 (8) |
C11—C4—C5—C6 | 180.0 (3) | C30—C29—C36—C37 | 123.5 (8) |
C4—C5—C6—C1 | 0.2 (4) | C28—C29—C36—C37 | −52.2 (9) |
C4—C5—C6—C15 | 177.8 (2) | C30—C29—C36—C39A | −31.2 (7) |
O2—C1—C6—C5 | 178.7 (2) | C28—C29—C36—C39A | 153.2 (6) |
C2—C1—C6—C5 | −1.2 (3) | C30—C29—C36—C38A | −141.8 (6) |
O2—C1—C6—C15 | 1.2 (4) | C28—C29—C36—C38A | 42.6 (6) |
C2—C1—C6—C15 | −178.7 (2) | C26—C31—C40—N2 | 2.7 (5) |
C3—C2—C7—C9 | 116.6 (3) | C30—C31—C40—N2 | −173.5 (3) |
C1—C2—C7—C9 | −62.8 (3) | C46—C41—C42—C43 | −2.5 (4) |
C3—C2—C7—C10 | −2.9 (4) | N2—C41—C42—C43 | 178.1 (3) |
C1—C2—C7—C10 | 177.7 (3) | C41—C42—C43—C44 | 0.4 (5) |
C3—C2—C7—C8 | −121.9 (3) | C42—C43—C44—N4 | −179.1 (3) |
C1—C2—C7—C8 | 58.7 (3) | C42—C43—C44—C45 | 1.5 (4) |
C5—C4—C11—C14 | 2.3 (4) | N4—C44—C45—C46 | 179.2 (3) |
C3—C4—C11—C14 | −178.8 (3) | C43—C44—C45—C46 | −1.4 (4) |
C5—C4—C11—C13A | −66.3 (9) | C44—C45—C46—C41 | −0.7 (5) |
C3—C4—C11—C13A | 112.7 (8) | C42—C41—C46—C45 | 2.6 (4) |
C5—C4—C11—C12 | 123.7 (3) | N2—C41—C46—C45 | −178.0 (3) |
C3—C4—C11—C12 | −57.3 (4) | C6—C15—N1—C16 | 177.9 (2) |
C5—C4—C11—C12A | 55.4 (9) | C6—C15—N1—CO1 | −4.9 (3) |
C3—C4—C11—C12A | −125.6 (9) | C17—C16—N1—C15 | 48.4 (3) |
C5—C4—C11—C13 | −115.8 (3) | C21—C16—N1—C15 | −130.9 (3) |
C3—C4—C11—C13 | 63.1 (4) | C17—C16—N1—CO1 | −128.7 (2) |
C5—C4—C11—C14A | 160.8 (10) | C21—C16—N1—CO1 | 52.0 (3) |
C3—C4—C11—C14A | −20.2 (10) | C31—C40—N2—C41 | 179.0 (3) |
C5—C6—C15—N1 | −175.3 (2) | C31—C40—N2—CO1 | 3.4 (4) |
C1—C6—C15—N1 | 2.2 (4) | C46—C41—N2—C40 | 29.8 (4) |
C21—C16—C17—C18 | 2.1 (4) | C42—C41—N2—C40 | −150.9 (3) |
N1—C16—C17—C18 | −177.2 (2) | C46—C41—N2—CO1 | −154.7 (2) |
C16—C17—C18—C19 | −0.2 (5) | C42—C41—N2—CO1 | 24.7 (3) |
C17—C18—C19—N3 | −179.3 (3) | C18—C19—N3—C22 | −13.0 (6) |
C17—C18—C19—C20 | −1.1 (5) | C20—C19—N3—C22 | 168.9 (4) |
N3—C19—C20—C21 | 178.7 (4) | C18—C19—N3—C24 | 179.4 (4) |
C18—C19—C20—C21 | 0.5 (5) | C20—C19—N3—C24 | 1.3 (6) |
C19—C20—C21—C16 | 1.4 (6) | C23—C22—N3—C19 | −71.5 (5) |
C17—C16—C21—C20 | −2.7 (5) | C23—C22—N3—C24 | 96.5 (5) |
N1—C16—C21—C20 | 176.7 (3) | C25—C24—N3—C19 | 83.3 (5) |
O1—C26—C27—C28 | 178.2 (3) | C25—C24—N3—C22 | −84.7 (5) |
C31—C26—C27—C28 | −1.9 (4) | C43—C44—N4—C47 | 168.8 (3) |
O1—C26—C27—C32 | −4.3 (4) | C45—C44—N4—C47 | −11.8 (5) |
C31—C26—C27—C32 | 175.7 (3) | C43—C44—N4—C49 | −0.8 (5) |
C26—C27—C28—C29 | 1.0 (5) | C45—C44—N4—C49 | 178.5 (3) |
C32—C27—C28—C29 | −176.5 (3) | C48—C47—N4—C44 | 88.3 (4) |
C27—C28—C29—C30 | −0.2 (5) | C48—C47—N4—C49 | −101.6 (4) |
C27—C28—C29—C36 | 175.8 (3) | C50—C49—N4—C44 | 83.7 (4) |
C28—C29—C30—C31 | 0.4 (5) | C50—C49—N4—C47 | −86.4 (4) |
C36—C29—C30—C31 | −175.4 (3) | C31—C26—O1—CO1 | −20.2 (4) |
O1—C26—C31—C30 | −178.0 (3) | C27—C26—O1—CO1 | 159.71 (19) |
C27—C26—C31—C30 | 2.1 (4) | C6—C1—O2—CO1 | −1.0 (3) |
O1—C26—C31—C40 | 5.9 (4) | C2—C1—O2—CO1 | 178.88 (16) |
C27—C26—C31—C40 | −174.0 (3) | C26—O1—CO1—O2 | −100.4 (2) |
C29—C30—C31—C26 | −1.4 (5) | C26—O1—CO1—N2 | 21.0 (2) |
C29—C30—C31—C40 | 175.1 (3) | C26—O1—CO1—N1 | 146.1 (2) |
C28—C27—C32—C34 | −120.6 (3) | C1—O2—CO1—O1 | −127.7 (2) |
C26—C27—C32—C34 | 62.0 (4) | C1—O2—CO1—N2 | 121.8 (2) |
C28—C27—C32—C33 | 117.9 (3) | C1—O2—CO1—N1 | −1.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8C···O2 | 0.96 | 2.31 | 2.936 (4) | 123 |
C9—H9C···O2 | 0.96 | 2.35 | 2.987 (4) | 123 |
C33—H33A···O1 | 0.96 | 2.34 | 2.980 (4) | 123 |
C34—H34A···O1 | 0.96 | 2.31 | 2.955 (4) | 124 |
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras, for the data collection.
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