metal-organic compounds
Bis{3,5-di-tert-butyl-N-[(4-dimethylamino)phenyl]salicylaldiminato}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 [systematic name: bis(2,4-di-tert-butyl-6-{N-[4-(dimethylamino)phenyl]carboximidoyl}phenolato)cobalt(II)], [Co(C23H31N2O)2], the cobalt(II) atom is coordinated by pairs of O and N atoms in a distorted tetrahedral coordination geometry. The dihedral angles formed by the aromatic rings of the same ligand are 51.99 (11) and 36.58 (9)°. The molecular conformation features weak intramolecular C—H⋯O hydrogen bonds. In the crystal, inversion-related pairs of complex molecules are linked into dimers by weak C—H⋯π interactions. The methyl C atoms of tert-butyl groups have rotational disorder, with site occupancies of 0.647 (7) and 0.617 (6) for the major components and 0.353 (7) and 0.383 (6) for the minor components. One of the methyl C atoms of the dimethylamino groups is also disordered over two orientations, with an occupancy ratio of 0.75 (4):0.25 (4).
CCDC reference: 1542611
Structure description
Metal complexes of N- and O-chelating ligands have attracted considerable attention because of their interesting physicochemical properties and pronounced biological activities. The N and O atoms play a key role in the coordination of metals at the active sites of numerous metallobimolecules (Nair et al., 2006). Schiff base–cobalt(II) metal complexes are constantly used in numerous applications varying from catalysis to pharmaceuticals (Holla et al., 2003). We herein report the synthesis and the structure of the title compound (Fig. 1). The metal cation has a distorted tetrahedral coordination geometry provided by two O and two N atoms. The Co—O distances [Co1—O1 = 1.8844 (19), Co1—O2 = 1.8882 (19), Co1—N1 = 1.980 (2), Co1—N2 = 1.984 (2) Å] agree well with the values observed in related structures (Adam et al., 1997; Chen et al., 2014, 2015).
The dihedral angle between the aromatic rings C1–C6 and C24–C29 is 85.85 (15)° while the C16–C21 ring makes a dihedral angle of 55.59 (17)° with the C39–C44 ring. The molecular conformation is stabilized by weak C—H⋯O hydrogen bonds (Table 1). The exhibits dimeric units formed by weak C—H⋯π interactions (Table 1) occurring between inversion-related complex molecules..
Synthesis and crystallization
Methanolic solutions of the Schiff base (1 mmol, 10 ml) and Co(AcO)2·H2O (0.5 mmol; 10 ml) were mixed thoroughly and boiled under reflux for 4–6 h, and then cooled to room temperature. The resulting precipitate was filtered, washed in ice-cold ethanol and dried in vacuo. X-ray quality single crystals were grown by layering a CHCl3 (3 ml) solution of the compound with CH3CN (5 ml).
Refinement
Crystal data, data collection and structure . The methyl C atoms of the tert-butyl groups exhibit rotational disorder, with site occupancies of 0.647 (7) (C12–C14) and 0.617 (6) (C36–C38) for the major components. One methyl C atom of the dimethylamino groups is disordered over two orientations with site occupancies of 0.75 (4) and 0.25 (4) for the major (C46A) and minor (C46) components, respectively. The anisotropic displacement parameters of the disordered C atoms were restrained by SIMU instructions within 0.001 standard deviations. DELU restraints were also applied. The C—C and C—N bond lengths involving the disordered atoms were restrained to 1.50 (1) and 1.40 (1) Å, respectively. A potential solvent-accessible void of 179 Å3 was detected but no residual electron density could be located in the final difference-Fourier map.
details are summarized in Table 2Structural data
CCDC reference: 1542611
https://doi.org/10.1107/S2414314617005259/rz4012sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005259/rz4012Isup2.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: SHELXL2016/4 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016/4 (Sheldrick, 2015) and PLATON (Spek, 2009).[Co(C23H31N2O)2] | Z = 2 |
Mr = 761.92 | F(000) = 818 |
Triclinic, P1 | Dx = 1.047 Mg m−3 |
a = 11.5598 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.3787 (4) Å | Cell parameters from 5165 reflections |
c = 17.3035 (5) Å | θ = 2.4–22.4° |
α = 111.756 (1)° | µ = 0.39 mm−1 |
β = 96.694 (2)° | T = 295 K |
γ = 98.293 (1)° | Block, colourless |
V = 2417.01 (12) Å3 | 0.34 × 0.30 × 0.26 mm |
Bruker Kappa APEXII CCD diffractometer | 6088 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.056 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | θmax = 26.1°, θmin = 2.0° |
Tmin = 0.691, Tmax = 0.905 | h = −14→14 |
41823 measured reflections | k = −16→16 |
9288 independent reflections | l = −21→21 |
Refinement on F2 | 100 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.175 | w = 1/[σ2(Fo2) + (0.0983P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
9288 reflections | Δρmax = 0.73 e Å−3 |
567 parameters | Δρmin = −0.42 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.2392 (3) | 0.3564 (2) | 0.32262 (16) | 0.0487 (6) | |
C2 | 0.3243 (3) | 0.3202 (2) | 0.36672 (17) | 0.0521 (7) | |
C3 | 0.2911 (3) | 0.2850 (2) | 0.42796 (18) | 0.0572 (8) | |
H3 | 0.346893 | 0.259851 | 0.455435 | 0.069* | |
C4 | 0.1792 (3) | 0.2847 (2) | 0.45161 (18) | 0.0569 (8) | |
C5 | 0.1001 (3) | 0.3215 (2) | 0.41019 (18) | 0.0588 (8) | |
H5 | 0.025030 | 0.322522 | 0.424485 | 0.071* | |
C6 | 0.1260 (3) | 0.3586 (2) | 0.34614 (18) | 0.0545 (7) | |
C7 | 0.4508 (3) | 0.3225 (3) | 0.3475 (2) | 0.0630 (8) | |
C8 | 0.5119 (3) | 0.4395 (3) | 0.3655 (2) | 0.0771 (10) | |
H8A | 0.591067 | 0.440021 | 0.353756 | 0.116* | |
H8B | 0.515485 | 0.485217 | 0.423896 | 0.116* | |
H8C | 0.467668 | 0.467191 | 0.330149 | 0.116* | |
C9 | 0.4461 (4) | 0.2495 (3) | 0.2558 (3) | 0.0921 (12) | |
H9A | 0.395195 | 0.271678 | 0.219923 | 0.138* | |
H9B | 0.415340 | 0.174508 | 0.246384 | 0.138* | |
H9C | 0.524698 | 0.256007 | 0.242988 | 0.138* | |
C10 | 0.5286 (4) | 0.2817 (4) | 0.4031 (3) | 0.1014 (14) | |
H10A | 0.493158 | 0.207711 | 0.393612 | 0.152* | |
H10B | 0.534843 | 0.328325 | 0.461670 | 0.152* | |
H10C | 0.606484 | 0.283637 | 0.388876 | 0.152* | |
C11 | 0.1529 (3) | 0.2444 (3) | 0.5206 (2) | 0.0769 (8) | |
C12 | 0.1685 (9) | 0.1236 (5) | 0.4929 (4) | 0.0885 (12) | 0.647 (7) |
H12A | 0.117868 | 0.079598 | 0.439116 | 0.133* | 0.647 (7) |
H12B | 0.147390 | 0.095968 | 0.534309 | 0.133* | 0.647 (7) |
H12C | 0.249872 | 0.120355 | 0.487947 | 0.133* | 0.647 (7) |
C13 | 0.2446 (7) | 0.3136 (6) | 0.6022 (4) | 0.0916 (15) | 0.647 (7) |
H13A | 0.322956 | 0.303763 | 0.592126 | 0.137* | 0.647 (7) |
H13B | 0.227103 | 0.290383 | 0.646548 | 0.137* | 0.647 (7) |
H13C | 0.241023 | 0.389810 | 0.618742 | 0.137* | 0.647 (7) |
C14 | 0.0284 (6) | 0.2520 (7) | 0.5411 (5) | 0.0919 (13) | 0.647 (7) |
H14A | 0.014724 | 0.324414 | 0.550798 | 0.138* | 0.647 (7) |
H14B | 0.022157 | 0.237374 | 0.590866 | 0.138* | 0.647 (7) |
H14C | −0.029876 | 0.198886 | 0.494298 | 0.138* | 0.647 (7) |
C12A | 0.0924 (15) | 0.1241 (7) | 0.4790 (7) | 0.0908 (14) | 0.353 (7) |
H12D | 0.092668 | 0.092999 | 0.520950 | 0.136* | 0.353 (7) |
H12E | 0.134447 | 0.085520 | 0.436326 | 0.136* | 0.353 (7) |
H12F | 0.011852 | 0.117418 | 0.453513 | 0.136* | 0.353 (7) |
C13A | 0.2612 (10) | 0.2610 (12) | 0.5856 (8) | 0.0911 (15) | 0.353 (7) |
H13D | 0.237021 | 0.264323 | 0.637544 | 0.137* | 0.353 (7) |
H13E | 0.314318 | 0.328509 | 0.595521 | 0.137* | 0.353 (7) |
H13F | 0.301098 | 0.200811 | 0.564899 | 0.137* | 0.353 (7) |
C14A | 0.0690 (12) | 0.3134 (12) | 0.5702 (8) | 0.0904 (16) | 0.353 (7) |
H14D | −0.006326 | 0.297730 | 0.533796 | 0.136* | 0.353 (7) |
H14E | 0.103741 | 0.390146 | 0.589833 | 0.136* | 0.353 (7) |
H14F | 0.057614 | 0.295111 | 0.617851 | 0.136* | 0.353 (7) |
C15 | 0.0334 (3) | 0.3962 (2) | 0.31094 (18) | 0.0563 (7) | |
H15 | −0.037059 | 0.390362 | 0.331465 | 0.068* | |
C16 | −0.0729 (3) | 0.4689 (2) | 0.22694 (17) | 0.0524 (7) | |
C17 | −0.1871 (3) | 0.4126 (3) | 0.2210 (2) | 0.0637 (8) | |
H17 | −0.195965 | 0.350816 | 0.234135 | 0.076* | |
C18 | −0.2850 (3) | 0.4452 (3) | 0.1967 (2) | 0.0727 (9) | |
H18 | −0.359553 | 0.406323 | 0.194602 | 0.087* | |
C19 | −0.2774 (3) | 0.5363 (3) | 0.1743 (2) | 0.0705 (9) | |
C20 | −0.1621 (3) | 0.5927 (3) | 0.1802 (2) | 0.0687 (9) | |
H20 | −0.152657 | 0.654627 | 0.167303 | 0.082* | |
C21 | −0.0632 (3) | 0.5580 (3) | 0.20448 (18) | 0.0594 (8) | |
H21 | 0.011820 | 0.595416 | 0.205829 | 0.071* | |
C22 | −0.3705 (5) | 0.6594 (5) | 0.1289 (4) | 0.151 (2) | |
H22A | −0.327061 | 0.723158 | 0.176810 | 0.226* | |
H22B | −0.449454 | 0.669574 | 0.114471 | 0.226* | |
H22C | −0.330701 | 0.648895 | 0.081687 | 0.226* | |
C23 | −0.4932 (4) | 0.5161 (5) | 0.1508 (4) | 0.151 (2) | |
H23A | −0.494799 | 0.439769 | 0.138368 | 0.227* | |
H23B | −0.550859 | 0.522928 | 0.109300 | 0.227* | |
H23C | −0.511786 | 0.550584 | 0.206005 | 0.227* | |
C24 | 0.2719 (2) | 0.6722 (2) | 0.20125 (16) | 0.0455 (6) | |
C25 | 0.3247 (3) | 0.7857 (2) | 0.24113 (18) | 0.0551 (7) | |
C26 | 0.3539 (3) | 0.8404 (3) | 0.1900 (2) | 0.0693 (9) | |
H26 | 0.389296 | 0.914604 | 0.216468 | 0.083* | |
C27 | 0.3342 (4) | 0.7929 (3) | 0.1020 (2) | 0.0741 (10) | |
C28 | 0.2816 (3) | 0.6844 (2) | 0.06418 (19) | 0.0621 (8) | |
H28 | 0.266534 | 0.650532 | 0.005385 | 0.075* | |
C29 | 0.2488 (2) | 0.6212 (2) | 0.11110 (16) | 0.0458 (6) | |
C30 | 0.1986 (2) | 0.5076 (2) | 0.06280 (16) | 0.0463 (6) | |
H30 | 0.184593 | 0.485998 | 0.004329 | 0.056* | |
C31 | 0.3491 (3) | 0.8427 (3) | 0.3376 (2) | 0.0731 (10) | |
C32 | 0.4384 (4) | 0.7915 (4) | 0.3751 (3) | 0.1115 (16) | |
H32A | 0.448902 | 0.823535 | 0.435723 | 0.167* | |
H32B | 0.513290 | 0.805160 | 0.358142 | 0.167* | |
H32C | 0.409178 | 0.713704 | 0.354919 | 0.167* | |
C33 | 0.2319 (4) | 0.8322 (3) | 0.3708 (2) | 0.0974 (13) | |
H33A | 0.177258 | 0.865466 | 0.347069 | 0.146* | |
H33B | 0.247505 | 0.868635 | 0.431381 | 0.146* | |
H33C | 0.197880 | 0.755883 | 0.354564 | 0.146* | |
C34 | 0.4014 (4) | 0.9676 (3) | 0.3675 (3) | 0.1069 (15) | |
H34A | 0.345418 | 1.001360 | 0.345413 | 0.160* | |
H34B | 0.474303 | 0.977415 | 0.347251 | 0.160* | |
H34C | 0.416611 | 1.001249 | 0.428225 | 0.160* | |
C35 | 0.3697 (5) | 0.8590 (3) | 0.0497 (3) | 0.1238 (15) | |
C36 | 0.3825 (11) | 0.9787 (5) | 0.0901 (6) | 0.1324 (18) | 0.617 (6) |
H36A | 0.457761 | 1.010161 | 0.128056 | 0.199* | 0.617 (6) |
H36B | 0.319442 | 0.995862 | 0.121122 | 0.199* | 0.617 (6) |
H36C | 0.378756 | 1.008537 | 0.047385 | 0.199* | 0.617 (6) |
C37 | 0.2571 (8) | 0.8347 (6) | −0.0220 (5) | 0.1301 (17) | 0.617 (6) |
H37A | 0.190961 | 0.856860 | 0.004003 | 0.195* | 0.617 (6) |
H37B | 0.237030 | 0.757545 | −0.056947 | 0.195* | 0.617 (6) |
H37C | 0.275610 | 0.875241 | −0.056114 | 0.195* | 0.617 (6) |
C38 | 0.4587 (9) | 0.8060 (7) | −0.0010 (6) | 0.1289 (17) | 0.617 (6) |
H38A | 0.471838 | 0.837219 | −0.041844 | 0.193* | 0.617 (6) |
H38B | 0.428227 | 0.728322 | −0.029810 | 0.193* | 0.617 (6) |
H38C | 0.532436 | 0.818811 | 0.036344 | 0.193* | 0.617 (6) |
C36A | 0.3089 (15) | 0.9562 (10) | 0.0745 (10) | 0.1322 (18) | 0.383 (6) |
H36D | 0.333634 | 1.002369 | 0.045685 | 0.198* | 0.383 (6) |
H36E | 0.330181 | 0.997481 | 0.134535 | 0.198* | 0.383 (6) |
H36F | 0.224215 | 0.930419 | 0.058881 | 0.198* | 0.383 (6) |
C37A | 0.3976 (17) | 0.8000 (11) | −0.0333 (7) | 0.1303 (19) | 0.383 (6) |
H37D | 0.434525 | 0.851823 | −0.053821 | 0.195* | 0.383 (6) |
H37E | 0.325697 | 0.756405 | −0.072038 | 0.195* | 0.383 (6) |
H37F | 0.451032 | 0.752984 | −0.028568 | 0.195* | 0.383 (6) |
C38A | 0.4954 (10) | 0.9361 (10) | 0.1014 (7) | 0.1305 (18) | 0.383 (6) |
H38D | 0.553657 | 0.891584 | 0.100900 | 0.196* | 0.383 (6) |
H38E | 0.488368 | 0.977080 | 0.158805 | 0.196* | 0.383 (6) |
H38F | 0.519715 | 0.986066 | 0.075569 | 0.196* | 0.383 (6) |
C39 | 0.1211 (3) | 0.3227 (2) | 0.02700 (17) | 0.0513 (7) | |
C40 | 0.0333 (3) | 0.3022 (3) | −0.04044 (19) | 0.0605 (8) | |
H40 | 0.002898 | 0.360479 | −0.045698 | 0.073* | |
C41 | −0.0110 (3) | 0.1980 (3) | −0.1005 (2) | 0.0742 (9) | |
H41 | −0.071273 | 0.186971 | −0.145150 | 0.089* | |
C42 | 0.0327 (4) | 0.1093 (3) | −0.0957 (2) | 0.0823 (11) | |
C43 | 0.1216 (4) | 0.1305 (3) | −0.0271 (3) | 0.1016 (15) | |
H43 | 0.153801 | 0.072747 | −0.022423 | 0.122* | |
C44 | 0.1630 (4) | 0.2342 (3) | 0.0339 (2) | 0.0834 (11) | |
H44 | 0.219977 | 0.245209 | 0.080453 | 0.100* | |
C45 | −0.0965 (6) | −0.0143 (4) | −0.2300 (3) | 0.143 (2) | |
H45A | −0.167146 | 0.009784 | −0.212692 | 0.215* | |
H45B | −0.116122 | −0.091118 | −0.266179 | 0.215* | |
H45C | −0.063260 | 0.026790 | −0.260142 | 0.215* | |
C46 | 0.063 (4) | −0.075 (3) | −0.164 (3) | 0.152 (6) | 0.25 (4) |
H46A | 0.136583 | −0.050238 | −0.177732 | 0.228* | 0.25 (4) |
H46B | 0.023307 | −0.144706 | −0.208211 | 0.228* | 0.25 (4) |
H46C | 0.078034 | −0.084242 | −0.111487 | 0.228* | 0.25 (4) |
C46A | 0.010 (2) | −0.0919 (8) | −0.1400 (9) | 0.155 (6) | 0.75 (4) |
H46D | 0.089134 | −0.101603 | −0.146220 | 0.233* | 0.75 (4) |
H46E | −0.046122 | −0.156089 | −0.179465 | 0.233* | 0.75 (4) |
H46F | −0.000541 | −0.081030 | −0.083336 | 0.233* | 0.75 (4) |
N1 | 0.0330 (2) | 0.43793 (18) | 0.25358 (14) | 0.0506 (6) | |
N2 | 0.1700 (2) | 0.43048 (17) | 0.08950 (13) | 0.0465 (5) | |
N3 | −0.3767 (3) | 0.5688 (4) | 0.1488 (2) | 0.1057 (12) | |
N4 | −0.0112 (4) | 0.0029 (3) | −0.1565 (2) | 0.1211 (14) | |
O1 | 0.26661 (18) | 0.38732 (17) | 0.26223 (12) | 0.0586 (5) | |
O2 | 0.24583 (18) | 0.61680 (15) | 0.24693 (11) | 0.0555 (5) | |
CO1 | 0.18236 (3) | 0.46551 (3) | 0.21245 (2) | 0.04969 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0650 (14) | 0.0425 (15) | 0.0427 (14) | 0.0144 (13) | 0.0106 (12) | 0.0201 (12) |
C2 | 0.068 (2) | 0.0421 (15) | 0.0498 (16) | 0.0136 (13) | 0.0111 (14) | 0.0206 (13) |
C3 | 0.074 (2) | 0.0530 (18) | 0.0533 (17) | 0.0214 (15) | 0.0070 (15) | 0.0296 (14) |
C4 | 0.078 (2) | 0.0535 (17) | 0.0477 (16) | 0.0153 (15) | 0.0127 (15) | 0.0278 (14) |
C5 | 0.071 (2) | 0.0628 (19) | 0.0530 (17) | 0.0158 (16) | 0.0174 (15) | 0.0315 (15) |
C6 | 0.0666 (16) | 0.0554 (17) | 0.0505 (16) | 0.0163 (14) | 0.0141 (12) | 0.0287 (13) |
C7 | 0.071 (2) | 0.066 (2) | 0.0652 (19) | 0.0236 (16) | 0.0148 (16) | 0.0361 (16) |
C8 | 0.083 (2) | 0.074 (2) | 0.077 (2) | 0.0095 (19) | 0.0156 (19) | 0.0350 (19) |
C9 | 0.097 (3) | 0.082 (3) | 0.090 (3) | 0.034 (2) | 0.031 (2) | 0.015 (2) |
C10 | 0.091 (3) | 0.135 (4) | 0.125 (4) | 0.051 (3) | 0.031 (3) | 0.090 (3) |
C11 | 0.111 (2) | 0.0800 (19) | 0.0583 (17) | 0.0217 (18) | 0.0234 (15) | 0.0449 (16) |
C12 | 0.126 (3) | 0.085 (2) | 0.076 (2) | 0.027 (2) | 0.022 (2) | 0.053 (2) |
C13 | 0.127 (3) | 0.096 (3) | 0.064 (2) | 0.026 (3) | 0.015 (2) | 0.045 (2) |
C14 | 0.118 (3) | 0.100 (3) | 0.080 (3) | 0.025 (3) | 0.035 (2) | 0.054 (2) |
C12A | 0.123 (3) | 0.093 (3) | 0.079 (2) | 0.024 (3) | 0.029 (2) | 0.054 (2) |
C13A | 0.128 (3) | 0.092 (3) | 0.071 (2) | 0.027 (3) | 0.016 (2) | 0.050 (2) |
C14A | 0.118 (3) | 0.099 (4) | 0.078 (3) | 0.029 (3) | 0.038 (3) | 0.053 (3) |
C15 | 0.0612 (16) | 0.0652 (19) | 0.0501 (16) | 0.0156 (14) | 0.0145 (13) | 0.0291 (14) |
C16 | 0.060 (2) | 0.0617 (18) | 0.0428 (14) | 0.0209 (15) | 0.0140 (13) | 0.0245 (13) |
C17 | 0.065 (2) | 0.067 (2) | 0.0631 (19) | 0.0134 (17) | 0.0117 (16) | 0.0302 (16) |
C18 | 0.061 (2) | 0.095 (3) | 0.068 (2) | 0.0235 (19) | 0.0130 (17) | 0.035 (2) |
C19 | 0.066 (2) | 0.105 (3) | 0.0531 (18) | 0.042 (2) | 0.0182 (16) | 0.0343 (19) |
C20 | 0.090 (3) | 0.079 (2) | 0.0600 (19) | 0.040 (2) | 0.0245 (17) | 0.0408 (17) |
C21 | 0.063 (2) | 0.073 (2) | 0.0563 (17) | 0.0219 (16) | 0.0161 (15) | 0.0372 (16) |
C22 | 0.128 (5) | 0.204 (6) | 0.199 (6) | 0.102 (4) | 0.050 (4) | 0.137 (5) |
C23 | 0.079 (4) | 0.197 (6) | 0.216 (7) | 0.071 (4) | 0.035 (4) | 0.106 (5) |
C24 | 0.0474 (16) | 0.0487 (16) | 0.0452 (15) | 0.0152 (12) | 0.0095 (12) | 0.0218 (13) |
C25 | 0.0591 (19) | 0.0501 (17) | 0.0531 (17) | 0.0097 (14) | 0.0086 (14) | 0.0179 (14) |
C26 | 0.093 (3) | 0.0420 (17) | 0.075 (2) | 0.0084 (16) | 0.0313 (19) | 0.0221 (16) |
C27 | 0.112 (3) | 0.0514 (19) | 0.070 (2) | 0.0149 (18) | 0.041 (2) | 0.0295 (17) |
C28 | 0.092 (2) | 0.0548 (19) | 0.0534 (17) | 0.0240 (16) | 0.0267 (16) | 0.0292 (15) |
C29 | 0.0518 (17) | 0.0464 (16) | 0.0458 (15) | 0.0145 (12) | 0.0136 (12) | 0.0227 (12) |
C30 | 0.0551 (17) | 0.0533 (17) | 0.0378 (13) | 0.0180 (13) | 0.0091 (12) | 0.0236 (12) |
C31 | 0.091 (3) | 0.059 (2) | 0.0564 (19) | 0.0043 (18) | 0.0025 (18) | 0.0159 (16) |
C32 | 0.121 (4) | 0.099 (3) | 0.083 (3) | 0.008 (3) | −0.039 (3) | 0.024 (2) |
C33 | 0.139 (4) | 0.080 (3) | 0.063 (2) | 0.021 (2) | 0.042 (2) | 0.0110 (19) |
C34 | 0.155 (4) | 0.063 (2) | 0.071 (2) | −0.002 (2) | 0.005 (3) | 0.004 (2) |
C35 | 0.223 (5) | 0.079 (2) | 0.100 (3) | 0.025 (2) | 0.080 (3) | 0.056 (2) |
C36 | 0.222 (5) | 0.080 (2) | 0.126 (3) | 0.027 (3) | 0.078 (3) | 0.063 (2) |
C37 | 0.224 (5) | 0.087 (2) | 0.118 (3) | 0.031 (3) | 0.077 (3) | 0.070 (2) |
C38 | 0.217 (5) | 0.089 (2) | 0.116 (3) | 0.026 (3) | 0.086 (3) | 0.066 (2) |
C36A | 0.223 (5) | 0.084 (2) | 0.124 (3) | 0.029 (3) | 0.076 (3) | 0.067 (3) |
C37A | 0.221 (5) | 0.090 (2) | 0.117 (3) | 0.028 (3) | 0.082 (3) | 0.068 (3) |
C38A | 0.219 (5) | 0.085 (2) | 0.121 (3) | 0.024 (3) | 0.082 (3) | 0.066 (3) |
C39 | 0.0624 (19) | 0.0498 (17) | 0.0451 (15) | 0.0113 (14) | 0.0098 (13) | 0.0225 (13) |
C40 | 0.063 (2) | 0.0558 (19) | 0.0617 (19) | 0.0130 (15) | 0.0015 (15) | 0.0246 (15) |
C41 | 0.081 (2) | 0.065 (2) | 0.063 (2) | 0.0063 (18) | −0.0075 (17) | 0.0180 (17) |
C42 | 0.117 (3) | 0.052 (2) | 0.060 (2) | 0.004 (2) | −0.001 (2) | 0.0122 (17) |
C43 | 0.162 (4) | 0.053 (2) | 0.080 (3) | 0.031 (2) | −0.013 (3) | 0.022 (2) |
C44 | 0.122 (3) | 0.055 (2) | 0.063 (2) | 0.022 (2) | −0.017 (2) | 0.0209 (17) |
C45 | 0.174 (5) | 0.098 (4) | 0.090 (3) | 0.009 (3) | −0.024 (3) | −0.018 (3) |
C46 | 0.298 (14) | 0.053 (4) | 0.101 (7) | 0.046 (7) | 0.024 (8) | 0.025 (4) |
C46A | 0.301 (14) | 0.057 (4) | 0.101 (7) | 0.039 (7) | 0.025 (7) | 0.025 (3) |
N1 | 0.0582 (15) | 0.0523 (14) | 0.0473 (13) | 0.0157 (11) | 0.0083 (11) | 0.0251 (11) |
N2 | 0.0561 (14) | 0.0433 (13) | 0.0424 (12) | 0.0138 (10) | 0.0055 (10) | 0.0192 (10) |
N3 | 0.084 (3) | 0.154 (4) | 0.122 (3) | 0.067 (2) | 0.026 (2) | 0.085 (3) |
N4 | 0.184 (4) | 0.057 (2) | 0.083 (2) | −0.001 (2) | −0.016 (2) | 0.0049 (18) |
O1 | 0.0688 (13) | 0.0738 (14) | 0.0542 (11) | 0.0259 (10) | 0.0205 (10) | 0.0417 (10) |
O2 | 0.0741 (14) | 0.0513 (11) | 0.0418 (10) | 0.0081 (9) | 0.0097 (9) | 0.0213 (9) |
CO1 | 0.0632 (3) | 0.0506 (3) | 0.0427 (2) | 0.01369 (18) | 0.01155 (17) | 0.02546 (18) |
C1—O1 | 1.313 (3) | C25—C31 | 1.527 (4) |
C1—C6 | 1.417 (4) | C26—C27 | 1.391 (5) |
C1—C2 | 1.421 (4) | C26—H26 | 0.9300 |
C2—C3 | 1.380 (4) | C27—C28 | 1.362 (4) |
C2—C7 | 1.535 (4) | C27—C35 | 1.532 (5) |
C3—C4 | 1.402 (4) | C28—C29 | 1.415 (4) |
C3—H3 | 0.9300 | C28—H28 | 0.9300 |
C4—C5 | 1.353 (4) | C29—C30 | 1.428 (4) |
C4—C11 | 1.524 (4) | C30—N2 | 1.295 (3) |
C5—C6 | 1.417 (4) | C30—H30 | 0.9300 |
C5—H5 | 0.9300 | C31—C32 | 1.528 (5) |
C6—C15 | 1.414 (4) | C31—C33 | 1.540 (5) |
C7—C9 | 1.513 (5) | C31—C34 | 1.556 (5) |
C7—C8 | 1.522 (4) | C32—H32A | 0.9600 |
C7—C10 | 1.537 (5) | C32—H32B | 0.9600 |
C8—H8A | 0.9600 | C32—H32C | 0.9600 |
C8—H8B | 0.9600 | C33—H33A | 0.9600 |
C8—H8C | 0.9600 | C33—H33B | 0.9600 |
C9—H9A | 0.9600 | C33—H33C | 0.9600 |
C9—H9B | 0.9600 | C34—H34A | 0.9600 |
C9—H9C | 0.9600 | C34—H34B | 0.9600 |
C10—H10A | 0.9600 | C34—H34C | 0.9600 |
C10—H10B | 0.9600 | C35—C37A | 1.459 (9) |
C10—H10C | 0.9600 | C35—C36 | 1.468 (7) |
C11—C13A | 1.512 (8) | C35—C38 | 1.513 (7) |
C11—C12A | 1.517 (8) | C35—C36A | 1.514 (9) |
C11—C14 | 1.530 (6) | C35—C37 | 1.594 (7) |
C11—C13 | 1.540 (6) | C35—C38A | 1.599 (9) |
C11—C14A | 1.547 (8) | C36—H36A | 0.9600 |
C11—C12 | 1.551 (6) | C36—H36B | 0.9600 |
C12—H12A | 0.9600 | C36—H36C | 0.9600 |
C12—H12B | 0.9600 | C37—H37A | 0.9600 |
C12—H12C | 0.9600 | C37—H37B | 0.9600 |
C13—H13A | 0.9600 | C37—H37C | 0.9600 |
C13—H13B | 0.9600 | C38—H38A | 0.9600 |
C13—H13C | 0.9600 | C38—H38B | 0.9600 |
C14—H14A | 0.9600 | C38—H38C | 0.9600 |
C14—H14B | 0.9600 | C36A—H36D | 0.9600 |
C14—H14C | 0.9600 | C36A—H36E | 0.9600 |
C12A—H12D | 0.9600 | C36A—H36F | 0.9600 |
C12A—H12E | 0.9600 | C37A—H37D | 0.9600 |
C12A—H12F | 0.9600 | C37A—H37E | 0.9600 |
C13A—H13D | 0.9600 | C37A—H37F | 0.9600 |
C13A—H13E | 0.9600 | C38A—H38D | 0.9600 |
C13A—H13F | 0.9600 | C38A—H38E | 0.9600 |
C14A—H14D | 0.9600 | C38A—H38F | 0.9600 |
C14A—H14E | 0.9600 | C39—C40 | 1.368 (4) |
C14A—H14F | 0.9600 | C39—C44 | 1.381 (4) |
C15—N1 | 1.307 (3) | C39—N2 | 1.426 (3) |
C15—H15 | 0.9300 | C40—C41 | 1.371 (4) |
C16—C21 | 1.378 (4) | C40—H40 | 0.9300 |
C16—C17 | 1.395 (4) | C41—C42 | 1.381 (5) |
C16—N1 | 1.428 (4) | C41—H41 | 0.9300 |
C17—C18 | 1.347 (5) | C42—C43 | 1.388 (5) |
C17—H17 | 0.9300 | C42—N4 | 1.395 (4) |
C18—C19 | 1.403 (5) | C43—C44 | 1.369 (5) |
C18—H18 | 0.9300 | C43—H43 | 0.9300 |
C19—N3 | 1.368 (4) | C44—H44 | 0.9300 |
C19—C20 | 1.406 (5) | C45—N4 | 1.439 (6) |
C20—C21 | 1.372 (4) | C45—H45A | 0.9600 |
C20—H20 | 0.9300 | C45—H45B | 0.9600 |
C21—H21 | 0.9300 | C45—H45C | 0.9600 |
C22—N3 | 1.372 (6) | C46—N4 | 1.424 (10) |
C22—H22A | 0.9600 | C46—H46A | 0.9600 |
C22—H22B | 0.9600 | C46—H46B | 0.9600 |
C22—H22C | 0.9600 | C46—H46C | 0.9600 |
C23—N3 | 1.437 (6) | C46A—N4 | 1.445 (10) |
C23—H23A | 0.9600 | C46A—H46D | 0.9600 |
C23—H23B | 0.9600 | C46A—H46E | 0.9600 |
C23—H23C | 0.9600 | C46A—H46F | 0.9600 |
C24—O2 | 1.300 (3) | N1—CO1 | 1.980 (2) |
C24—C25 | 1.418 (4) | N2—CO1 | 1.984 (2) |
C24—C29 | 1.425 (4) | O1—CO1 | 1.8844 (19) |
C25—C26 | 1.382 (4) | O2—CO1 | 1.8882 (19) |
O1—C1—C6 | 121.6 (2) | C27—C28—H28 | 118.8 |
O1—C1—C2 | 120.1 (3) | C29—C28—H28 | 118.8 |
C6—C1—C2 | 118.2 (2) | C28—C29—C24 | 119.2 (3) |
C3—C2—C1 | 118.5 (3) | C28—C29—C30 | 116.0 (2) |
C3—C2—C7 | 121.0 (3) | C24—C29—C30 | 124.7 (2) |
C1—C2—C7 | 120.5 (2) | N2—C30—C29 | 128.7 (2) |
C2—C3—C4 | 124.5 (3) | N2—C30—H30 | 115.7 |
C2—C3—H3 | 117.8 | C29—C30—H30 | 115.7 |
C4—C3—H3 | 117.8 | C25—C31—C32 | 109.6 (3) |
C5—C4—C3 | 116.2 (3) | C25—C31—C33 | 109.7 (3) |
C5—C4—C11 | 124.0 (3) | C32—C31—C33 | 110.7 (3) |
C3—C4—C11 | 119.8 (3) | C25—C31—C34 | 111.2 (3) |
C4—C5—C6 | 123.2 (3) | C32—C31—C34 | 108.5 (3) |
C4—C5—H5 | 118.4 | C33—C31—C34 | 107.1 (3) |
C6—C5—H5 | 118.4 | C31—C32—H32A | 109.5 |
C15—C6—C1 | 125.3 (3) | C31—C32—H32B | 109.5 |
C15—C6—C5 | 115.4 (3) | H32A—C32—H32B | 109.5 |
C1—C6—C5 | 119.3 (3) | C31—C32—H32C | 109.5 |
C9—C7—C8 | 109.9 (3) | H32A—C32—H32C | 109.5 |
C9—C7—C2 | 109.9 (3) | H32B—C32—H32C | 109.5 |
C8—C7—C2 | 110.2 (3) | C31—C33—H33A | 109.5 |
C9—C7—C10 | 108.0 (3) | C31—C33—H33B | 109.5 |
C8—C7—C10 | 106.8 (3) | H33A—C33—H33B | 109.5 |
C2—C7—C10 | 112.0 (3) | C31—C33—H33C | 109.5 |
C7—C8—H8A | 109.5 | H33A—C33—H33C | 109.5 |
C7—C8—H8B | 109.5 | H33B—C33—H33C | 109.5 |
H8A—C8—H8B | 109.5 | C31—C34—H34A | 109.5 |
C7—C8—H8C | 109.5 | C31—C34—H34B | 109.5 |
H8A—C8—H8C | 109.5 | H34A—C34—H34B | 109.5 |
H8B—C8—H8C | 109.5 | C31—C34—H34C | 109.5 |
C7—C9—H9A | 109.5 | H34A—C34—H34C | 109.5 |
C7—C9—H9B | 109.5 | H34B—C34—H34C | 109.5 |
H9A—C9—H9B | 109.5 | C36—C35—C38 | 122.2 (6) |
C7—C9—H9C | 109.5 | C37A—C35—C36A | 126.9 (10) |
H9A—C9—H9C | 109.5 | C37A—C35—C27 | 118.0 (6) |
H9B—C9—H9C | 109.5 | C36—C35—C27 | 117.0 (5) |
C7—C10—H10A | 109.5 | C38—C35—C27 | 107.6 (4) |
C7—C10—H10B | 109.5 | C36A—C35—C27 | 107.2 (6) |
H10A—C10—H10B | 109.5 | C36—C35—C37 | 97.9 (6) |
C7—C10—H10C | 109.5 | C38—C35—C37 | 102.5 (6) |
H10A—C10—H10C | 109.5 | C27—C35—C37 | 106.8 (4) |
H10B—C10—H10C | 109.5 | C37A—C35—C38A | 102.2 (10) |
C13A—C11—C12A | 110.5 (7) | C36A—C35—C38A | 91.4 (9) |
C13A—C11—C4 | 114.1 (6) | C27—C35—C38A | 104.6 (5) |
C12A—C11—C4 | 108.6 (5) | C35—C36—H36A | 109.5 |
C4—C11—C14 | 113.7 (3) | C35—C36—H36B | 109.5 |
C4—C11—C13 | 109.0 (4) | H36A—C36—H36B | 109.5 |
C14—C11—C13 | 108.3 (5) | C35—C36—H36C | 109.5 |
C13A—C11—C14A | 105.7 (8) | H36A—C36—H36C | 109.5 |
C12A—C11—C14A | 110.2 (7) | H36B—C36—H36C | 109.5 |
C4—C11—C14A | 107.7 (5) | C35—C37—H37A | 109.5 |
C4—C11—C12 | 108.8 (3) | C35—C37—H37B | 109.5 |
C14—C11—C12 | 109.4 (4) | H37A—C37—H37B | 109.5 |
C13—C11—C12 | 107.5 (4) | C35—C37—H37C | 109.5 |
C11—C12—H12A | 109.5 | H37A—C37—H37C | 109.5 |
C11—C12—H12B | 109.5 | H37B—C37—H37C | 109.5 |
H12A—C12—H12B | 109.5 | C35—C38—H38A | 109.5 |
C11—C12—H12C | 109.5 | C35—C38—H38B | 109.5 |
H12A—C12—H12C | 109.5 | H38A—C38—H38B | 109.5 |
H12B—C12—H12C | 109.5 | C35—C38—H38C | 109.5 |
C11—C13—H13A | 109.5 | H38A—C38—H38C | 109.5 |
C11—C13—H13B | 109.5 | H38B—C38—H38C | 109.5 |
H13A—C13—H13B | 109.5 | C35—C36A—H36D | 109.5 |
C11—C13—H13C | 109.5 | C35—C36A—H36E | 109.5 |
H13A—C13—H13C | 109.5 | H36D—C36A—H36E | 109.5 |
H13B—C13—H13C | 109.5 | C35—C36A—H36F | 109.5 |
C11—C14—H14A | 109.5 | H36D—C36A—H36F | 109.5 |
C11—C14—H14B | 109.5 | H36E—C36A—H36F | 109.5 |
H14A—C14—H14B | 109.5 | C35—C37A—H37D | 109.5 |
C11—C14—H14C | 109.5 | C35—C37A—H37E | 109.5 |
H14A—C14—H14C | 109.5 | H37D—C37A—H37E | 109.5 |
H14B—C14—H14C | 109.5 | C35—C37A—H37F | 109.5 |
C11—C12A—H12D | 109.5 | H37D—C37A—H37F | 109.5 |
C11—C12A—H12E | 109.5 | H37E—C37A—H37F | 109.5 |
H12D—C12A—H12E | 109.5 | C35—C38A—H38D | 109.5 |
C11—C12A—H12F | 109.5 | C35—C38A—H38E | 109.5 |
H12D—C12A—H12F | 109.5 | H38D—C38A—H38E | 109.5 |
H12E—C12A—H12F | 109.5 | C35—C38A—H38F | 109.5 |
C11—C13A—H13D | 109.5 | H38D—C38A—H38F | 109.5 |
C11—C13A—H13E | 109.5 | H38E—C38A—H38F | 109.5 |
H13D—C13A—H13E | 109.5 | C40—C39—C44 | 117.7 (3) |
C11—C13A—H13F | 109.5 | C40—C39—N2 | 122.9 (3) |
H13D—C13A—H13F | 109.5 | C44—C39—N2 | 119.4 (3) |
H13E—C13A—H13F | 109.5 | C39—C40—C41 | 121.8 (3) |
C11—C14A—H14D | 109.5 | C39—C40—H40 | 119.1 |
C11—C14A—H14E | 109.5 | C41—C40—H40 | 119.1 |
H14D—C14A—H14E | 109.5 | C40—C41—C42 | 121.0 (3) |
C11—C14A—H14F | 109.5 | C40—C41—H41 | 119.5 |
H14D—C14A—H14F | 109.5 | C42—C41—H41 | 119.5 |
H14E—C14A—H14F | 109.5 | C41—C42—C43 | 116.9 (3) |
N1—C15—C6 | 129.0 (3) | C41—C42—N4 | 121.6 (4) |
N1—C15—H15 | 115.5 | C43—C42—N4 | 121.4 (4) |
C6—C15—H15 | 115.5 | C44—C43—C42 | 121.8 (3) |
C21—C16—C17 | 117.5 (3) | C44—C43—H43 | 119.1 |
C21—C16—N1 | 119.0 (3) | C42—C43—H43 | 119.1 |
C17—C16—N1 | 123.4 (3) | C43—C44—C39 | 120.7 (3) |
C18—C17—C16 | 121.7 (3) | C43—C44—H44 | 119.7 |
C18—C17—H17 | 119.1 | C39—C44—H44 | 119.7 |
C16—C17—H17 | 119.1 | N4—C45—H45A | 109.5 |
C17—C18—C19 | 121.8 (3) | N4—C45—H45B | 109.5 |
C17—C18—H18 | 119.1 | H45A—C45—H45B | 109.5 |
C19—C18—H18 | 119.1 | N4—C45—H45C | 109.5 |
N3—C19—C18 | 121.8 (4) | H45A—C45—H45C | 109.5 |
N3—C19—C20 | 121.9 (4) | H45B—C45—H45C | 109.5 |
C18—C19—C20 | 116.3 (3) | N4—C46—H46A | 109.5 |
C21—C20—C19 | 121.3 (3) | N4—C46—H46B | 109.5 |
C21—C20—H20 | 119.4 | H46A—C46—H46B | 109.5 |
C19—C20—H20 | 119.4 | N4—C46—H46C | 109.5 |
C20—C21—C16 | 121.3 (3) | H46A—C46—H46C | 109.5 |
C20—C21—H21 | 119.3 | H46B—C46—H46C | 109.5 |
C16—C21—H21 | 119.3 | N4—C46A—H46D | 109.5 |
N3—C22—H22A | 109.5 | N4—C46A—H46E | 109.5 |
N3—C22—H22B | 109.5 | H46D—C46A—H46E | 109.5 |
H22A—C22—H22B | 109.5 | N4—C46A—H46F | 109.5 |
N3—C22—H22C | 109.5 | H46D—C46A—H46F | 109.5 |
H22A—C22—H22C | 109.5 | H46E—C46A—H46F | 109.5 |
H22B—C22—H22C | 109.5 | C15—N1—C16 | 118.8 (2) |
N3—C23—H23A | 109.5 | C15—N1—CO1 | 118.8 (2) |
N3—C23—H23B | 109.5 | C16—N1—CO1 | 122.19 (18) |
H23A—C23—H23B | 109.5 | C30—N2—C39 | 117.2 (2) |
N3—C23—H23C | 109.5 | C30—N2—CO1 | 120.48 (18) |
H23A—C23—H23C | 109.5 | C39—N2—CO1 | 122.15 (17) |
H23B—C23—H23C | 109.5 | C19—N3—C22 | 122.3 (4) |
O2—C24—C25 | 119.9 (2) | C19—N3—C23 | 120.8 (4) |
O2—C24—C29 | 121.3 (2) | C22—N3—C23 | 116.5 (4) |
C25—C24—C29 | 118.7 (2) | C42—N4—C45 | 119.6 (4) |
C26—C25—C24 | 117.8 (3) | C42—N4—C46A | 121.1 (5) |
C26—C25—C31 | 122.3 (3) | C45—N4—C46A | 118.3 (6) |
C24—C25—C31 | 119.8 (3) | C1—O1—CO1 | 126.92 (18) |
C25—C26—C27 | 124.9 (3) | C24—O2—CO1 | 129.44 (17) |
C25—C26—H26 | 117.5 | O1—CO1—O2 | 117.06 (9) |
C27—C26—H26 | 117.5 | O1—CO1—N1 | 96.23 (9) |
C28—C27—C26 | 116.9 (3) | O2—CO1—N1 | 112.64 (9) |
C28—C27—C35 | 121.2 (3) | O1—CO1—N2 | 119.77 (9) |
C26—C27—C35 | 121.9 (3) | O2—CO1—N2 | 95.20 (8) |
C27—C28—C29 | 122.4 (3) | N1—CO1—N2 | 117.31 (9) |
O1—C1—C2—C3 | −178.0 (3) | C25—C24—C29—C30 | 178.6 (3) |
C6—C1—C2—C3 | 2.5 (4) | C28—C29—C30—N2 | 174.1 (3) |
O1—C1—C2—C7 | 3.1 (4) | C24—C29—C30—N2 | −3.2 (5) |
C6—C1—C2—C7 | −176.4 (3) | C26—C25—C31—C32 | −116.3 (4) |
C1—C2—C3—C4 | −1.6 (4) | C24—C25—C31—C32 | 62.8 (4) |
C7—C2—C3—C4 | 177.3 (3) | C26—C25—C31—C33 | 122.0 (4) |
C2—C3—C4—C5 | 0.2 (5) | C24—C25—C31—C33 | −58.9 (4) |
C2—C3—C4—C11 | −179.6 (3) | C26—C25—C31—C34 | 3.7 (5) |
C3—C4—C5—C6 | 0.2 (5) | C24—C25—C31—C34 | −177.2 (3) |
C11—C4—C5—C6 | 180.0 (3) | C28—C27—C35—C37A | −27.5 (11) |
O1—C1—C6—C15 | −2.0 (5) | C26—C27—C35—C37A | 152.6 (10) |
C2—C1—C6—C15 | 177.5 (3) | C28—C27—C35—C36 | 157.3 (7) |
O1—C1—C6—C5 | 178.3 (3) | C26—C27—C35—C36 | −22.6 (9) |
C2—C1—C6—C5 | −2.2 (4) | C28—C27—C35—C38 | −60.5 (7) |
C4—C5—C6—C15 | −178.8 (3) | C26—C27—C35—C38 | 119.6 (6) |
C4—C5—C6—C1 | 0.9 (5) | C28—C27—C35—C36A | 123.7 (8) |
C3—C2—C7—C9 | 120.3 (3) | C26—C27—C35—C36A | −56.2 (9) |
C1—C2—C7—C9 | −60.8 (4) | C28—C27—C35—C37 | 48.9 (6) |
C3—C2—C7—C8 | −118.5 (3) | C26—C27—C35—C37 | −131.0 (5) |
C1—C2—C7—C8 | 60.4 (3) | C28—C27—C35—C38A | −140.2 (6) |
C3—C2—C7—C10 | 0.2 (4) | C26—C27—C35—C38A | 39.9 (7) |
C1—C2—C7—C10 | 179.1 (3) | C44—C39—C40—C41 | −1.1 (5) |
C5—C4—C11—C13A | −151.0 (7) | N2—C39—C40—C41 | 178.9 (3) |
C3—C4—C11—C13A | 28.8 (8) | C39—C40—C41—C42 | −0.8 (5) |
C5—C4—C11—C12A | 85.3 (8) | C40—C41—C42—C43 | 0.8 (6) |
C3—C4—C11—C12A | −94.9 (8) | C40—C41—C42—N4 | −179.7 (4) |
C5—C4—C11—C14 | −1.4 (6) | C41—C42—C43—C44 | 1.1 (7) |
C3—C4—C11—C14 | 178.4 (4) | N4—C42—C43—C44 | −178.4 (4) |
C5—C4—C11—C13 | −122.3 (5) | C42—C43—C44—C39 | −3.0 (7) |
C3—C4—C11—C13 | 57.6 (5) | C40—C39—C44—C43 | 3.0 (6) |
C5—C4—C11—C14A | −34.0 (8) | N2—C39—C44—C43 | −177.1 (4) |
C3—C4—C11—C14A | 145.8 (7) | C6—C15—N1—C16 | 179.2 (3) |
C5—C4—C11—C12 | 120.8 (5) | C6—C15—N1—CO1 | −5.0 (4) |
C3—C4—C11—C12 | −59.4 (5) | C21—C16—N1—C15 | 146.7 (3) |
C1—C6—C15—N1 | −2.1 (5) | C17—C16—N1—C15 | −34.3 (4) |
C5—C6—C15—N1 | 177.6 (3) | C21—C16—N1—CO1 | −29.0 (3) |
C21—C16—C17—C18 | −1.9 (4) | C17—C16—N1—CO1 | 150.0 (2) |
N1—C16—C17—C18 | 179.1 (3) | C29—C30—N2—C39 | −179.9 (3) |
C16—C17—C18—C19 | 1.3 (5) | C29—C30—N2—CO1 | 4.9 (4) |
C17—C18—C19—N3 | 179.3 (3) | C40—C39—N2—C30 | −46.4 (4) |
C17—C18—C19—C20 | −1.1 (5) | C44—C39—N2—C30 | 133.7 (3) |
N3—C19—C20—C21 | −178.8 (3) | C40—C39—N2—CO1 | 128.7 (3) |
C18—C19—C20—C21 | 1.5 (5) | C44—C39—N2—CO1 | −51.2 (4) |
C19—C20—C21—C16 | −2.3 (5) | C18—C19—N3—C22 | 178.2 (4) |
C17—C16—C21—C20 | 2.4 (4) | C20—C19—N3—C22 | −1.4 (6) |
N1—C16—C21—C20 | −178.6 (3) | C18—C19—N3—C23 | 5.4 (6) |
O2—C24—C25—C26 | 178.2 (3) | C20—C19—N3—C23 | −174.2 (4) |
C29—C24—C25—C26 | −1.6 (4) | C41—C42—N4—C45 | 5.4 (7) |
O2—C24—C25—C31 | −0.9 (4) | C43—C42—N4—C45 | −175.1 (5) |
C29—C24—C25—C31 | 179.3 (3) | C41—C42—N4—C46A | −162.7 (14) |
C24—C25—C26—C27 | 0.7 (5) | C43—C42—N4—C46A | 16.7 (15) |
C31—C25—C26—C27 | 179.8 (3) | C6—C1—O1—CO1 | 13.7 (4) |
C25—C26—C27—C28 | 0.4 (6) | C2—C1—O1—CO1 | −165.78 (19) |
C25—C26—C27—C35 | −179.6 (4) | C25—C24—O2—CO1 | −176.91 (19) |
C26—C27—C28—C29 | −0.7 (5) | C29—C24—O2—CO1 | 2.9 (4) |
C35—C27—C28—C29 | 179.4 (4) | C1—O1—CO1—O2 | 102.9 (2) |
C27—C28—C29—C24 | −0.3 (5) | C1—O1—CO1—N1 | −16.5 (2) |
C27—C28—C29—C30 | −177.7 (3) | C1—O1—CO1—N2 | −143.0 (2) |
O2—C24—C29—C28 | −178.4 (3) | C24—O2—CO1—O1 | 126.3 (2) |
C25—C24—C29—C28 | 1.4 (4) | C24—O2—CO1—N1 | −123.5 (2) |
O2—C24—C29—C30 | −1.3 (4) | C24—O2—CO1—N2 | −1.1 (2) |
Cg is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8C···O1 | 0.96 | 2.38 | 3.007 (4) | 123 |
C9—H9A···O1 | 0.96 | 2.28 | 2.953 (4) | 126 |
C32—H32C···O2 | 0.96 | 2.33 | 2.974 (4) | 124 |
C33—H33C···O2 | 0.96 | 2.28 | 2.925 (4) | 124 |
C45—H45B···Cgi | 0.96 | 2.96 | 3.914 (5) | 171 |
Symmetry code: (i) −x, −y, −z. |
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras for the data collection.
References
Adam, K. R., Anderson, P. A., Astley, T., Atkinson, I. M., Charnock, J. M., Garner, C. D., Gulbis, J. M., Hambley, T. W., Hitchman, M. A., Keene, F. R. & Tiekink, E. R. T. (1997). J. Chem. Soc. Dalton Trans. pp. 519–530. CSD CrossRef Web of Science Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Y. M., Gao, Q., Chen, W. Q., Gao, D. D., Li, Y. H., Liu, W. & Li, W. (2015). Chem. Asian J. 10, 411–421. Web of Science CSD CrossRef CAS PubMed Google Scholar
Chen, Y. M., Gao, Q., Zhang, H. F., Gao, D. D., Li, Y. H., Liu, W. & Li, W. (2014). Polyhedron, 71, 91–98. Web of Science CSD CrossRef CAS Google Scholar
Holla, B. S., Veerendra, B., Shivananda, M. K. & Poojary, B. (2003). Eur. J. Med. Chem. 38, 759–767. Web of Science CrossRef PubMed Google Scholar
Nair, B., Shah, A., Baluja, S. & Chanda, S. (2006). J. Serb. Chem. Soc. 71, 733–744. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.