organic compounds
tert-Butyl 4-{3-[6-(4-methoxyphenyl)-2-methylpyrimidin-4-yl]quinolin-2-yl}piperazine-1-carboxylate
aDepartment of Physics, University of Jammu, Jammu Tawi 180 006, India, bSchool of Physics, Shri Mata Vaishno Devi University, Katra 182 320, J&K, India, cDepartment of Chemistry, University College of Science, Tumkur University Tumkur 572 103, India, and dDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India
*Correspondence e-mail: rkant.ju@gmail.com
The 30H33N5O3, contains two independent molecules, A and B. In molecule A, the tert-butyl 4-methylpiperazine-1-carboxylate group was refined as disordered over two sets of sites with an occupancy ratio of 0.821 (4):0.179 (4). The piperazine ring adopts a chair conformation in both molecules. The dihedral angles between the pyrimidine ring and methoxyphenyl ring are 20.27 (14) and 8.72 (11)° for molecules A and B, respectively. The quinoline ring system makes dihedral angles of 30.68 (11) and 37.76 (10)° with the pyrimidine ring in molecules A and B, respectively. In the crystal, C—H⋯O hydrogen bonds link the molecules into chains along [100].
of the title compound, CKeywords: crystal structure; quinoline; pyrimidine; direct method; intermolecular hydrogen bonding.
CCDC reference: 1829297
Structure description
Pyrimidine and its derivatives have a diverse array of biological and pharmacological activities including anticonvulsant, antibacterial, antifungal, antiviral and anticancer properties (Jain et al., 2006). An SAR study of the pyrimidine nucleus revealed that substitution at different positions may lead to compounds with a variation in their biological activities (Khanage et al., 2012). Compounds with a pyrimidine ring substituted at the 2 and 4 positions with keto or amino or mixed keto–amino groups have shown anticancer, antiviral, antibacterial and antifungal activity and are used in the treatment of respiratory tract infections and liver disorders. Substitution at the 5 and 6 positions with a heterocyclic ring or a substituted aryl ring leads to anticancer, antiviral, antibacterial and vasodilation activity and such compounds are also used in the treatment of urinary tract infections (Selvam et al., 2012). On the other hand, quinoline derivatives also find importance owing to their wide occurrence in natural products and in biologically active compounds (Markees et al., 1970; Campbell et al., 1988; Kalluraya & Sreenivasa, 1998). As part of our studies in this area, we now describe the synthesis and structure of the title compound.
The A and B (Figs. 1 and 2). In both the molecules, the piperazine ring adopts a chair conformation. In the major occupancy component of disordered molecule A [0.821 (5) occupancy], the best mirror plane passes through atoms N4A and N5A and the best twofold rotational axis bisects the N5A—C23A bond [asymmetry parameter Cs(N4A) = 2.53 and C2(N5A—C23A) = 1.91] whereas for the minor [0.179 (5)] occupancy component, the best mirror plane passes through atoms C23C and C25C and the best twofold rotational axis bisects the C22C—C23C bond [asymmetry parameter Cs(C23C) = 1.06 and C2(C22C—C23C) = 0.71]. In molecule B, the best mirror plane passes through atoms N4B and N5B and the best twofold rotational axis bisects the N5B—C24B bond [asymmetry parameter Cs(N4B) = 0.54 and C2(N5B—C24B) = 5.2] (Duax & Norton, 1975). All bond lengths are in normal ranges and are comparable with those in previously reported related structures (Prasath et al., 2010, 2011; Sharma et al., 2017; Singh et al., 2018). The dihedral angle between the pyrimidine and methoxyphenyl rings is 20.27 (14)° in molecule A and 8.72 (11)° in molecule B while the pyrimidine ring makes a dihedral angle of 30.68 (11)° in A and 37.76 (10)° in B with the quinoline ring system. The quinoline units are essentially planar with a maximum deviation of 0.0851 (1) Å for atom C21A and 0.0607 (1) Å for C21B.
of the title compound comprises two independent molecules,In the crystal, adjacent molecules are linked by C—H⋯O hydrogen bonds, forming chains along [100] (Table 1 and Fig. 3).
Synthesis and crystallization
2-(4-N-Boc-piperazin-1-yl) quinoline chalcone (1000 mg, 0.00258 mmol), acetamidine hydrochloride (199 mg, 0.002211 mmol) and NaOH (253 mg, 0.00633 mmol) were refluxed for 12 h in ethanol. The progress of the reaction was monitored by thin layer
After the completion of reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under vacuum using a rotary evaporator to obtain a solid that was purified by using 60–120 mesh silica gel. Crystals of the title compound were obtained by recrystallization from ethyl acetate solution.Refinement
Crystal data, data collection and structure . Disorder was modeled for the tert-butyl 4-methyl piperazine-1-carboxylate group in molecule A with an occupancy ratio of 0.821 (4):0.179 (4). In addition, the methyl H atoms attached to C12A and C12B are also disordered with occupancy ratios of 0.68 (4):0.32 (4) and 0.53 (4):0.47 (4), respectively.
details are summarized in Table 2Structural data
CCDC reference: 1829297
https://doi.org/10.1107/S2414314618004273/lh4032sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004273/lh4032Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618004273/lh4032Isup3.cml
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).C30H33N5O3 | Z = 4 |
Mr = 511.61 | F(000) = 1088 |
Triclinic, P1 | Dx = 1.203 Mg m−3 |
a = 11.0894 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.6875 (6) Å | Cell parameters from 4885 reflections |
c = 20.8953 (9) Å | θ = 3.8–26.6° |
α = 83.663 (4)° | µ = 0.08 mm−1 |
β = 75.335 (4)° | T = 293 K |
γ = 86.259 (4)° | Block, white |
V = 2824.6 (2) Å3 | 0.30 × 0.20 × 0.20 mm |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 9886 independent reflections |
Radiation source: fine-focus sealed tube | 5244 reflections with I > 2σ(I) |
Detector resolution: 6.1049 pixels mm-1 | Rint = 0.042 |
ω scans | θmax = 25.0°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | h = −13→13 |
Tmin = 0.869, Tmax = 1.000 | k = −15→15 |
19560 measured reflections | l = −24→24 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.065 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.4039P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.181 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.27 e Å−3 |
9886 reflections | Δρmin = −0.21 e Å−3 |
751 parameters | Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
32 restraints | Extinction coefficient: 0.0055 (7) |
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 were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å; and with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1A | 0.4112 (2) | 0.24904 (15) | 0.89015 (12) | 0.0782 (7) | |
N1A | 0.4291 (2) | 0.74137 (18) | 0.90707 (12) | 0.0547 (7) | |
N2A | 0.3208 (2) | 0.90807 (18) | 0.89406 (12) | 0.0549 (7) | |
N3A | −0.0740 (2) | 0.95687 (18) | 0.83629 (12) | 0.0535 (7) | |
C1A | 0.3435 (4) | 0.1902 (2) | 0.8577 (2) | 0.0910 (13) | |
H1AA | 0.364378 | 0.115925 | 0.864713 | 0.137* | |
H1AB | 0.364741 | 0.212412 | 0.810897 | 0.137* | |
H1AC | 0.255635 | 0.202571 | 0.875508 | 0.137* | |
C2A | 0.3901 (3) | 0.3566 (2) | 0.88660 (16) | 0.0557 (8) | |
C3A | 0.4511 (3) | 0.4105 (2) | 0.92207 (17) | 0.0631 (9) | |
H3AA | 0.503422 | 0.373218 | 0.945828 | 0.076* | |
C4A | 0.4352 (3) | 0.5183 (2) | 0.92263 (16) | 0.0577 (8) | |
H4AA | 0.477179 | 0.553336 | 0.946796 | 0.069* | |
C5A | 0.3575 (3) | 0.5764 (2) | 0.88772 (13) | 0.0439 (7) | |
C6A | 0.2974 (3) | 0.5202 (2) | 0.85269 (15) | 0.0553 (8) | |
H6AA | 0.244421 | 0.556792 | 0.829052 | 0.066* | |
C7A | 0.3135 (3) | 0.4115 (2) | 0.85170 (16) | 0.0607 (9) | |
H7AA | 0.272351 | 0.375925 | 0.827392 | 0.073* | |
C8A | 0.3410 (3) | 0.6926 (2) | 0.88887 (13) | 0.0441 (7) | |
C9A | 0.2394 (3) | 0.7501 (2) | 0.87395 (13) | 0.0461 (7) | |
H9AA | 0.177416 | 0.716377 | 0.862080 | 0.055* | |
C10A | 0.2319 (3) | 0.8586 (2) | 0.87707 (13) | 0.0447 (7) | |
C11A | 0.4142 (3) | 0.8467 (2) | 0.90806 (16) | 0.0573 (8) | |
C12A | 0.5128 (3) | 0.9007 (3) | 0.9286 (2) | 0.0883 (12) | |
H12D | 0.523039 | 0.866999 | 0.970447 | 0.132* | 0.68 (4) |
H12E | 0.488240 | 0.974079 | 0.932971 | 0.132* | 0.68 (4) |
H12F | 0.590317 | 0.895735 | 0.895541 | 0.132* | 0.68 (4) |
H12X | 0.544692 | 0.957543 | 0.895526 | 0.132* | 0.32 (4) |
H12Y | 0.579490 | 0.850463 | 0.933001 | 0.132* | 0.32 (4) |
H12Z | 0.477414 | 0.928807 | 0.970432 | 0.132* | 0.32 (4) |
C13A | 0.1206 (3) | 0.9268 (2) | 0.86981 (14) | 0.0453 (7) | |
C14A | 0.0897 (3) | 1.0104 (2) | 0.90780 (14) | 0.0514 (8) | |
H14B | 0.144325 | 1.027588 | 0.931943 | 0.062* | |
C15A | −0.0226 (3) | 1.0711 (2) | 0.91138 (14) | 0.0517 (8) | |
C16A | −0.0554 (3) | 1.1607 (2) | 0.94699 (15) | 0.0657 (9) | |
H16B | −0.000588 | 1.182985 | 0.969415 | 0.079* | |
C17A | −0.1658 (4) | 1.2153 (3) | 0.94927 (17) | 0.0763 (11) | |
H17B | −0.185662 | 1.275867 | 0.971721 | 0.092* | |
C18A | −0.2483 (4) | 1.1787 (3) | 0.91735 (18) | 0.0811 (12) | |
H18B | −0.325076 | 1.214441 | 0.919940 | 0.097* | |
C19A | −0.2206 (3) | 1.0926 (3) | 0.88262 (17) | 0.0693 (10) | |
H19B | −0.278427 | 1.070025 | 0.862175 | 0.083* | |
C20A | −0.1046 (3) | 1.0368 (2) | 0.87717 (15) | 0.0534 (8) | |
C21A | 0.0360 (3) | 0.9066 (2) | 0.83122 (14) | 0.0471 (7) | |
N4A | 0.0650 (6) | 0.8296 (5) | 0.7862 (3) | 0.046 (2) | 0.821 (4) |
N5A | 0.1156 (4) | 0.7165 (3) | 0.67279 (16) | 0.0595 (10) | 0.821 (4) |
C22A | 0.1768 (6) | 0.8494 (5) | 0.7325 (3) | 0.0569 (17) | 0.821 (4) |
H22A | 0.243242 | 0.869194 | 0.750750 | 0.068* | 0.821 (4) |
H22B | 0.159489 | 0.908089 | 0.701780 | 0.068* | 0.821 (4) |
C23A | 0.2187 (5) | 0.7528 (4) | 0.6955 (2) | 0.0584 (12) | 0.821 (4) |
H23A | 0.288056 | 0.769940 | 0.657650 | 0.070* | 0.821 (4) |
H23B | 0.246730 | 0.696709 | 0.724492 | 0.070* | 0.821 (4) |
C24A | 0.0010 (5) | 0.7023 (3) | 0.7245 (2) | 0.0648 (12) | 0.821 (4) |
H24A | 0.012995 | 0.643983 | 0.756743 | 0.078* | 0.821 (4) |
H24B | −0.064906 | 0.684583 | 0.705132 | 0.078* | 0.821 (4) |
C25A | −0.0367 (5) | 0.8018 (4) | 0.7589 (3) | 0.0580 (14) | 0.821 (4) |
H25A | −0.054339 | 0.859274 | 0.727514 | 0.070* | 0.821 (4) |
H25B | −0.111648 | 0.790413 | 0.794376 | 0.070* | 0.821 (4) |
O2A | 0.0461 (3) | 0.6256 (2) | 0.60292 (15) | 0.0806 (10) | 0.821 (4) |
O3A | 0.2454 (3) | 0.6779 (3) | 0.57806 (16) | 0.0736 (10) | 0.821 (4) |
C26A | 0.1296 (4) | 0.6692 (3) | 0.6160 (2) | 0.0618 (12) | 0.821 (4) |
C27A | 0.2787 (4) | 0.6395 (4) | 0.51153 (19) | 0.0716 (13) | 0.821 (4) |
C28A | 0.1984 (12) | 0.6966 (7) | 0.4686 (3) | 0.115 (5) | 0.821 (4) |
H28D | 0.112601 | 0.680592 | 0.487811 | 0.173* | 0.821 (4) |
H28E | 0.224041 | 0.673604 | 0.424767 | 0.173* | 0.821 (4) |
H28F | 0.207761 | 0.771734 | 0.466098 | 0.173* | 0.821 (4) |
C29A | 0.4124 (4) | 0.6716 (4) | 0.4865 (2) | 0.1048 (19) | 0.821 (4) |
H29D | 0.460597 | 0.638089 | 0.515867 | 0.157* | 0.821 (4) |
H29E | 0.415776 | 0.747231 | 0.484935 | 0.157* | 0.821 (4) |
H29F | 0.445958 | 0.649747 | 0.442710 | 0.157* | 0.821 (4) |
C30A | 0.2686 (11) | 0.5201 (6) | 0.5179 (5) | 0.122 (6) | 0.821 (4) |
H30D | 0.308103 | 0.488397 | 0.551669 | 0.182* | 0.821 (4) |
H30E | 0.308971 | 0.493401 | 0.476254 | 0.182* | 0.821 (4) |
H30F | 0.182220 | 0.502811 | 0.529939 | 0.182* | 0.821 (4) |
N4C | 0.085 (2) | 0.836 (2) | 0.7815 (14) | 0.047 (12)* | 0.179 (4) |
N5C | 0.1755 (15) | 0.7272 (14) | 0.6637 (7) | 0.060 (6)* | 0.179 (4) |
C22C | 0.206 (2) | 0.8579 (18) | 0.7344 (14) | 0.031 (6)* | 0.179 (4) |
H22E | 0.262662 | 0.880194 | 0.758237 | 0.037* | 0.179 (4) |
H22F | 0.194262 | 0.915838 | 0.701871 | 0.037* | 0.179 (4) |
C23C | 0.2630 (15) | 0.763 (2) | 0.6988 (11) | 0.072 (10)* | 0.179 (4) |
H23E | 0.340864 | 0.781375 | 0.667239 | 0.087* | 0.179 (4) |
H23F | 0.280618 | 0.705894 | 0.730595 | 0.087* | 0.179 (4) |
C24C | 0.0558 (16) | 0.7045 (16) | 0.7084 (10) | 0.058 (8)* | 0.179 (4) |
H24E | 0.065108 | 0.644200 | 0.739854 | 0.070* | 0.179 (4) |
H24F | −0.000913 | 0.685885 | 0.683268 | 0.070* | 0.179 (4) |
C25C | 0.0015 (17) | 0.7984 (18) | 0.7456 (13) | 0.050 (8)* | 0.179 (4) |
H25E | −0.017292 | 0.855714 | 0.714419 | 0.060* | 0.179 (4) |
H25F | −0.076294 | 0.779032 | 0.777063 | 0.060* | 0.179 (4) |
O2C | 0.3282 (13) | 0.6920 (11) | 0.5751 (7) | 0.073 (5)* | 0.179 (4) |
O3C | 0.1338 (15) | 0.6351 (13) | 0.5861 (7) | 0.083 (6)* | 0.179 (4) |
C26C | 0.2201 (14) | 0.6809 (16) | 0.6060 (7) | 0.046 (6)* | 0.179 (4) |
C27C | 0.1653 (14) | 0.5955 (12) | 0.5196 (7) | 0.070 (6)* | 0.179 (4) |
C28C | 0.204 (4) | 0.6879 (19) | 0.4671 (11) | 0.065 (13)* | 0.179 (4) |
H28A | 0.224656 | 0.662758 | 0.423825 | 0.098* | 0.179 (4) |
H28B | 0.136505 | 0.739899 | 0.470207 | 0.098* | 0.179 (4) |
H28C | 0.275499 | 0.719316 | 0.474140 | 0.098* | 0.179 (4) |
C29C | 0.0406 (14) | 0.5576 (13) | 0.5176 (9) | 0.076 (6)* | 0.179 (4) |
H29A | 0.047717 | 0.529127 | 0.476050 | 0.114* | 0.179 (4) |
H29B | 0.013994 | 0.503444 | 0.553492 | 0.114* | 0.179 (4) |
H29C | −0.019517 | 0.616014 | 0.522018 | 0.114* | 0.179 (4) |
C30C | 0.264 (3) | 0.507 (2) | 0.5163 (17) | 0.10 (2)* | 0.179 (4) |
H30A | 0.284381 | 0.482174 | 0.473014 | 0.145* | 0.179 (4) |
H30B | 0.337996 | 0.533877 | 0.524238 | 0.145* | 0.179 (4) |
H30C | 0.234172 | 0.450245 | 0.549386 | 0.145* | 0.179 (4) |
O1B | 0.4659 (2) | 1.16589 (17) | 0.28836 (13) | 0.0853 (8) | |
N1B | 0.4623 (2) | 0.66522 (19) | 0.30835 (12) | 0.0557 (7) | |
N2B | 0.3734 (2) | 0.52099 (18) | 0.27451 (12) | 0.0551 (7) | |
N3B | 0.0359 (2) | 0.55788 (18) | 0.16688 (12) | 0.0520 (6) | |
N4B | 0.0356 (2) | 0.66254 (17) | 0.25152 (11) | 0.0498 (6) | |
N5B | −0.1124 (2) | 0.7906 (2) | 0.34538 (12) | 0.0630 (8) | |
C1B | 0.3905 (4) | 1.2467 (3) | 0.26348 (19) | 0.0943 (13) | |
H1BA | 0.422597 | 1.314778 | 0.264531 | 0.141* | |
H1BB | 0.306494 | 1.243604 | 0.290543 | 0.141* | |
H1BC | 0.391224 | 1.236430 | 0.218548 | 0.141* | |
C2B | 0.4366 (3) | 1.0626 (2) | 0.28821 (16) | 0.0606 (9) | |
C3B | 0.3370 (3) | 1.0326 (2) | 0.26817 (17) | 0.0663 (9) | |
H3BA | 0.282413 | 1.083486 | 0.254246 | 0.080* | |
C4B | 0.3181 (3) | 0.9249 (2) | 0.26880 (16) | 0.0619 (9) | |
H4BA | 0.249447 | 0.904575 | 0.255800 | 0.074* | |
C5B | 0.3986 (3) | 0.8478 (2) | 0.28824 (14) | 0.0488 (7) | |
C6B | 0.4954 (3) | 0.8812 (2) | 0.31091 (15) | 0.0598 (9) | |
H6BA | 0.548875 | 0.830766 | 0.326207 | 0.072* | |
C7B | 0.5143 (3) | 0.9874 (2) | 0.31135 (16) | 0.0647 (9) | |
H7BA | 0.579421 | 1.008000 | 0.327225 | 0.078* | |
C8B | 0.3852 (3) | 0.7341 (2) | 0.28273 (14) | 0.0471 (7) | |
C9B | 0.3023 (3) | 0.6982 (2) | 0.25148 (14) | 0.0506 (8) | |
H9BA | 0.250663 | 0.745740 | 0.232552 | 0.061* | |
C10B | 0.2974 (3) | 0.5898 (2) | 0.24882 (13) | 0.0468 (7) | |
C11B | 0.4525 (3) | 0.5623 (2) | 0.30273 (15) | 0.0577 (9) | |
C12B | 0.5392 (4) | 0.4855 (3) | 0.33093 (18) | 0.0829 (12) | |
H12A | 0.494706 | 0.424178 | 0.353327 | 0.124* | 0.53 (4) |
H12B | 0.571196 | 0.519033 | 0.361898 | 0.124* | 0.53 (4) |
H12C | 0.607200 | 0.464357 | 0.295566 | 0.124* | 0.53 (4) |
H12H | 0.620695 | 0.514201 | 0.320534 | 0.124* | 0.47 (4) |
H12I | 0.544205 | 0.419346 | 0.311963 | 0.124* | 0.47 (4) |
H12J | 0.508201 | 0.474022 | 0.378295 | 0.124* | 0.47 (4) |
C13B | 0.2175 (3) | 0.5448 (2) | 0.21209 (14) | 0.0460 (7) | |
C14B | 0.2663 (3) | 0.4644 (2) | 0.17423 (14) | 0.0513 (8) | |
H14A | 0.342992 | 0.432813 | 0.177178 | 0.062* | |
C15B | 0.2034 (3) | 0.4276 (2) | 0.13054 (15) | 0.0507 (8) | |
C16B | 0.2510 (3) | 0.3443 (2) | 0.09124 (16) | 0.0642 (9) | |
H16A | 0.326080 | 0.309344 | 0.094095 | 0.077* | |
C17B | 0.1869 (4) | 0.3149 (3) | 0.04889 (18) | 0.0759 (10) | |
H17A | 0.217222 | 0.258515 | 0.023653 | 0.091* | |
C18B | 0.0765 (4) | 0.3686 (3) | 0.04325 (18) | 0.0782 (11) | |
H18A | 0.034490 | 0.348840 | 0.013448 | 0.094* | |
C19B | 0.0286 (3) | 0.4503 (3) | 0.08085 (16) | 0.0684 (9) | |
H19A | −0.045362 | 0.485812 | 0.076405 | 0.082* | |
C20B | 0.0911 (3) | 0.4806 (2) | 0.12621 (15) | 0.0505 (8) | |
C21B | 0.0952 (3) | 0.5863 (2) | 0.20887 (14) | 0.0459 (7) | |
C22B | −0.0774 (3) | 0.7163 (2) | 0.23884 (15) | 0.0597 (9) | |
H22C | −0.146901 | 0.669642 | 0.254401 | 0.072* | |
H22D | −0.066387 | 0.734848 | 0.191477 | 0.072* | |
C23B | −0.1044 (3) | 0.8159 (2) | 0.27487 (15) | 0.0661 (10) | |
H23C | −0.038772 | 0.865391 | 0.255923 | 0.079* | |
H23D | −0.182533 | 0.849538 | 0.269037 | 0.079* | |
C24B | −0.0071 (3) | 0.7270 (3) | 0.36064 (16) | 0.0706 (10) | |
H24C | −0.025227 | 0.704896 | 0.407932 | 0.085* | |
H24D | 0.066415 | 0.769326 | 0.349080 | 0.085* | |
C25B | 0.0178 (3) | 0.6312 (2) | 0.32272 (14) | 0.0609 (9) | |
H25C | 0.091885 | 0.592583 | 0.330594 | 0.073* | |
H25D | −0.051874 | 0.584688 | 0.338109 | 0.073* | |
O2B | −0.2597 (2) | 0.9194 (2) | 0.37400 (12) | 0.0920 (9) | |
O3B | −0.1626 (2) | 0.8354 (2) | 0.44866 (12) | 0.0929 (9) | |
C26B | −0.1844 (3) | 0.8539 (3) | 0.38876 (17) | 0.0651 (9) | |
C27B | −0.2333 (5) | 0.8896 (4) | 0.5058 (2) | 0.0995 (14) | |
C28B | −0.3655 (5) | 0.8573 (5) | 0.5203 (3) | 0.181 (3) | |
H28G | −0.401764 | 0.886628 | 0.484821 | 0.271* | |
H28H | −0.411978 | 0.883339 | 0.561224 | 0.271* | |
H28I | −0.367602 | 0.781332 | 0.524297 | 0.271* | |
C29B | −0.1713 (6) | 0.8443 (5) | 0.5595 (2) | 0.182 (3) | |
H29G | −0.082931 | 0.853015 | 0.544378 | 0.274* | |
H29H | −0.187609 | 0.770219 | 0.569941 | 0.274* | |
H29I | −0.203714 | 0.880877 | 0.598506 | 0.274* | |
C30B | −0.2271 (7) | 1.0048 (4) | 0.4932 (3) | 0.186 (3) | |
H30G | −0.276743 | 1.030462 | 0.462799 | 0.280* | |
H30H | −0.142085 | 1.023623 | 0.474388 | 0.280* | |
H30I | −0.258472 | 1.036247 | 0.534293 | 0.280* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0893 (18) | 0.0390 (12) | 0.108 (2) | 0.0004 (12) | −0.0272 (16) | −0.0079 (12) |
N1A | 0.0546 (16) | 0.0462 (14) | 0.0688 (17) | −0.0004 (12) | −0.0213 (14) | −0.0169 (12) |
N2A | 0.0581 (16) | 0.0428 (14) | 0.0682 (18) | −0.0056 (12) | −0.0198 (14) | −0.0126 (12) |
N3A | 0.0581 (17) | 0.0504 (14) | 0.0517 (16) | 0.0005 (13) | −0.0136 (13) | −0.0055 (12) |
C1A | 0.101 (3) | 0.048 (2) | 0.125 (4) | −0.014 (2) | −0.020 (3) | −0.023 (2) |
C2A | 0.059 (2) | 0.0412 (18) | 0.065 (2) | −0.0049 (15) | −0.0103 (17) | −0.0049 (15) |
C3A | 0.063 (2) | 0.0474 (18) | 0.085 (2) | 0.0040 (16) | −0.0331 (19) | −0.0003 (17) |
C4A | 0.060 (2) | 0.0477 (18) | 0.072 (2) | −0.0038 (15) | −0.0272 (18) | −0.0056 (16) |
C5A | 0.0491 (18) | 0.0383 (15) | 0.0447 (17) | −0.0046 (13) | −0.0109 (14) | −0.0051 (13) |
C6A | 0.064 (2) | 0.0456 (17) | 0.062 (2) | 0.0003 (15) | −0.0264 (17) | −0.0083 (15) |
C7A | 0.079 (2) | 0.0421 (17) | 0.068 (2) | −0.0072 (16) | −0.0286 (19) | −0.0107 (15) |
C8A | 0.0508 (18) | 0.0411 (16) | 0.0408 (16) | −0.0022 (14) | −0.0095 (14) | −0.0093 (12) |
C9A | 0.0554 (19) | 0.0400 (16) | 0.0481 (17) | −0.0066 (14) | −0.0209 (15) | −0.0056 (13) |
C10A | 0.0523 (18) | 0.0391 (16) | 0.0438 (17) | −0.0012 (14) | −0.0125 (15) | −0.0070 (13) |
C11A | 0.057 (2) | 0.0511 (19) | 0.070 (2) | −0.0077 (16) | −0.0217 (18) | −0.0173 (16) |
C12A | 0.076 (3) | 0.063 (2) | 0.142 (4) | −0.0108 (19) | −0.044 (3) | −0.032 (2) |
C13A | 0.0521 (18) | 0.0370 (15) | 0.0469 (17) | −0.0064 (13) | −0.0117 (15) | −0.0024 (13) |
C14A | 0.060 (2) | 0.0443 (16) | 0.0505 (18) | −0.0061 (15) | −0.0131 (16) | −0.0057 (14) |
C15A | 0.063 (2) | 0.0421 (16) | 0.0436 (18) | 0.0016 (15) | −0.0038 (16) | −0.0019 (13) |
C16A | 0.087 (3) | 0.0550 (19) | 0.051 (2) | 0.0082 (18) | −0.0082 (19) | −0.0168 (15) |
C17A | 0.095 (3) | 0.066 (2) | 0.058 (2) | 0.019 (2) | −0.003 (2) | −0.0138 (17) |
C18A | 0.083 (3) | 0.080 (3) | 0.068 (3) | 0.028 (2) | −0.001 (2) | −0.010 (2) |
C19A | 0.063 (2) | 0.075 (2) | 0.064 (2) | 0.0113 (18) | −0.0084 (19) | −0.0092 (18) |
C20A | 0.057 (2) | 0.0494 (18) | 0.0446 (18) | 0.0043 (15) | −0.0003 (16) | 0.0020 (14) |
C21A | 0.0544 (19) | 0.0398 (16) | 0.0439 (17) | −0.0049 (14) | −0.0067 (15) | −0.0009 (13) |
N4A | 0.049 (3) | 0.047 (3) | 0.044 (3) | −0.007 (2) | −0.0084 (18) | −0.0108 (17) |
N5A | 0.061 (3) | 0.071 (2) | 0.046 (2) | −0.012 (2) | −0.004 (2) | −0.0205 (17) |
C22A | 0.059 (4) | 0.062 (3) | 0.053 (3) | −0.008 (3) | −0.014 (3) | −0.0139 (19) |
C23A | 0.056 (3) | 0.074 (3) | 0.045 (3) | −0.001 (3) | −0.008 (2) | −0.016 (2) |
C24A | 0.065 (3) | 0.064 (3) | 0.066 (3) | −0.015 (2) | −0.007 (3) | −0.021 (2) |
C25A | 0.050 (3) | 0.066 (3) | 0.059 (3) | −0.007 (2) | −0.009 (3) | −0.017 (2) |
O2A | 0.088 (3) | 0.092 (2) | 0.068 (2) | −0.0160 (19) | −0.0164 (19) | −0.0331 (16) |
O3A | 0.073 (3) | 0.101 (2) | 0.047 (2) | −0.0036 (19) | −0.0081 (19) | −0.0239 (18) |
C26A | 0.066 (3) | 0.059 (3) | 0.062 (3) | −0.006 (2) | −0.017 (3) | −0.010 (2) |
C27A | 0.076 (3) | 0.100 (3) | 0.038 (2) | 0.011 (3) | −0.011 (2) | −0.021 (2) |
C28A | 0.115 (7) | 0.174 (9) | 0.064 (4) | 0.007 (5) | −0.044 (4) | −0.002 (4) |
C29A | 0.092 (4) | 0.163 (5) | 0.057 (3) | 0.006 (4) | −0.005 (3) | −0.039 (3) |
C30A | 0.159 (9) | 0.108 (7) | 0.103 (7) | 0.031 (4) | −0.031 (4) | −0.061 (5) |
O1B | 0.108 (2) | 0.0496 (14) | 0.108 (2) | −0.0091 (13) | −0.0438 (17) | −0.0097 (13) |
N1B | 0.0653 (17) | 0.0537 (15) | 0.0557 (16) | 0.0090 (13) | −0.0282 (14) | −0.0135 (12) |
N2B | 0.0672 (18) | 0.0518 (15) | 0.0516 (15) | 0.0078 (13) | −0.0257 (14) | −0.0075 (12) |
N3B | 0.0561 (16) | 0.0524 (14) | 0.0489 (15) | −0.0057 (12) | −0.0149 (13) | −0.0043 (12) |
N4B | 0.0564 (16) | 0.0491 (14) | 0.0442 (14) | 0.0047 (12) | −0.0156 (13) | −0.0025 (11) |
N5B | 0.0701 (18) | 0.0679 (17) | 0.0520 (17) | 0.0253 (14) | −0.0206 (15) | −0.0134 (13) |
C1B | 0.130 (4) | 0.049 (2) | 0.106 (3) | 0.004 (2) | −0.039 (3) | 0.002 (2) |
C2B | 0.069 (2) | 0.050 (2) | 0.065 (2) | −0.0040 (17) | −0.0184 (19) | −0.0080 (16) |
C3B | 0.073 (2) | 0.053 (2) | 0.078 (2) | 0.0089 (17) | −0.029 (2) | −0.0076 (17) |
C4B | 0.063 (2) | 0.059 (2) | 0.072 (2) | 0.0022 (17) | −0.0307 (18) | −0.0136 (16) |
C5B | 0.0519 (19) | 0.0482 (17) | 0.0494 (18) | 0.0014 (14) | −0.0178 (15) | −0.0083 (14) |
C6B | 0.060 (2) | 0.058 (2) | 0.065 (2) | 0.0051 (16) | −0.0235 (18) | −0.0092 (16) |
C7B | 0.067 (2) | 0.054 (2) | 0.081 (2) | −0.0037 (17) | −0.033 (2) | −0.0084 (17) |
C8B | 0.0467 (18) | 0.0489 (17) | 0.0456 (17) | 0.0016 (14) | −0.0130 (15) | −0.0030 (14) |
C9B | 0.0528 (19) | 0.0492 (18) | 0.0518 (18) | 0.0018 (14) | −0.0193 (16) | −0.0008 (14) |
C10B | 0.0510 (18) | 0.0490 (17) | 0.0394 (16) | −0.0004 (14) | −0.0090 (14) | −0.0062 (13) |
C11B | 0.069 (2) | 0.058 (2) | 0.0498 (19) | 0.0130 (17) | −0.0233 (17) | −0.0114 (15) |
C12B | 0.101 (3) | 0.070 (2) | 0.094 (3) | 0.027 (2) | −0.056 (2) | −0.018 (2) |
C13B | 0.0490 (18) | 0.0441 (16) | 0.0457 (17) | −0.0028 (13) | −0.0143 (15) | −0.0007 (13) |
C14B | 0.0511 (19) | 0.0492 (17) | 0.0535 (19) | −0.0024 (14) | −0.0122 (16) | −0.0058 (14) |
C15B | 0.0499 (19) | 0.0531 (18) | 0.0503 (18) | −0.0103 (15) | −0.0113 (16) | −0.0072 (14) |
C16B | 0.067 (2) | 0.061 (2) | 0.066 (2) | −0.0021 (17) | −0.0137 (19) | −0.0208 (17) |
C17B | 0.077 (3) | 0.079 (2) | 0.074 (3) | −0.006 (2) | −0.012 (2) | −0.0313 (19) |
C18B | 0.084 (3) | 0.089 (3) | 0.071 (2) | −0.015 (2) | −0.024 (2) | −0.032 (2) |
C19B | 0.064 (2) | 0.082 (2) | 0.067 (2) | −0.0052 (18) | −0.0238 (19) | −0.0199 (19) |
C20B | 0.053 (2) | 0.0516 (17) | 0.0480 (18) | −0.0096 (15) | −0.0121 (16) | −0.0074 (14) |
C21B | 0.0525 (19) | 0.0441 (16) | 0.0416 (17) | −0.0030 (14) | −0.0139 (15) | 0.0002 (13) |
C22B | 0.058 (2) | 0.070 (2) | 0.056 (2) | 0.0096 (17) | −0.0245 (17) | −0.0090 (16) |
C23B | 0.081 (2) | 0.065 (2) | 0.054 (2) | 0.0225 (18) | −0.0256 (19) | −0.0060 (16) |
C24B | 0.078 (2) | 0.082 (2) | 0.051 (2) | 0.027 (2) | −0.0206 (19) | −0.0126 (17) |
C25B | 0.068 (2) | 0.063 (2) | 0.0486 (19) | 0.0104 (17) | −0.0133 (17) | 0.0002 (16) |
O2B | 0.099 (2) | 0.0923 (18) | 0.0857 (19) | 0.0430 (16) | −0.0306 (16) | −0.0226 (14) |
O3B | 0.108 (2) | 0.112 (2) | 0.0537 (15) | 0.0459 (17) | −0.0173 (15) | −0.0233 (14) |
C26B | 0.070 (2) | 0.062 (2) | 0.060 (2) | 0.0113 (18) | −0.013 (2) | −0.0101 (17) |
C27B | 0.107 (4) | 0.125 (4) | 0.063 (3) | 0.032 (3) | −0.012 (3) | −0.037 (2) |
C28B | 0.119 (5) | 0.277 (8) | 0.124 (5) | −0.027 (5) | 0.031 (4) | −0.060 (5) |
C29B | 0.210 (7) | 0.267 (7) | 0.069 (3) | 0.102 (6) | −0.041 (4) | −0.060 (4) |
C30B | 0.289 (9) | 0.119 (4) | 0.166 (6) | 0.028 (5) | −0.067 (6) | −0.073 (4) |
O1A—C2A | 1.367 (3) | O2C—C26C | 1.218 (10) |
O1A—C1A | 1.423 (4) | O3C—C26C | 1.325 (9) |
N1A—C11A | 1.337 (3) | O3C—C27C | 1.480 (10) |
N1A—C8A | 1.342 (3) | C27C—C29C | 1.505 (10) |
N2A—C11A | 1.328 (4) | C27C—C30C | 1.511 (12) |
N2A—C10A | 1.341 (3) | C27C—C28C | 1.518 (12) |
N3A—C21A | 1.325 (3) | C28C—H28A | 0.9600 |
N3A—C20A | 1.368 (4) | C28C—H28B | 0.9600 |
C1A—H1AA | 0.9600 | C28C—H28C | 0.9600 |
C1A—H1AB | 0.9600 | C29C—H29A | 0.9600 |
C1A—H1AC | 0.9600 | C29C—H29B | 0.9600 |
C2A—C7A | 1.365 (4) | C29C—H29C | 0.9600 |
C2A—C3A | 1.378 (4) | C30C—H30A | 0.9600 |
C3A—C4A | 1.369 (4) | C30C—H30B | 0.9600 |
C3A—H3AA | 0.9300 | C30C—H30C | 0.9600 |
C4A—C5A | 1.391 (4) | O1B—C2B | 1.371 (4) |
C4A—H4AA | 0.9300 | O1B—C1B | 1.419 (4) |
C5A—C6A | 1.383 (4) | N1B—C11B | 1.338 (4) |
C5A—C8A | 1.476 (3) | N1B—C8B | 1.346 (3) |
C6A—C7A | 1.380 (4) | N2B—C11B | 1.335 (4) |
C6A—H6AA | 0.9300 | N2B—C10B | 1.337 (3) |
C7A—H7AA | 0.9300 | N3B—C21B | 1.314 (3) |
C8A—C9A | 1.386 (4) | N3B—C20B | 1.379 (3) |
C9A—C10A | 1.382 (3) | N4B—C21B | 1.405 (3) |
C9A—H9AA | 0.9300 | N4B—C22B | 1.457 (3) |
C10A—C13A | 1.491 (4) | N4B—C25B | 1.463 (3) |
C11A—C12A | 1.500 (4) | N5B—C26B | 1.347 (4) |
C12A—H12D | 0.9600 | N5B—C23B | 1.454 (4) |
C12A—H12E | 0.9600 | N5B—C24B | 1.458 (4) |
C12A—H12F | 0.9600 | C1B—H1BA | 0.9600 |
C12A—H12X | 0.9600 | C1B—H1BB | 0.9600 |
C12A—H12Y | 0.9600 | C1B—H1BC | 0.9600 |
C12A—H12Z | 0.9600 | C2B—C3B | 1.365 (4) |
C13A—C14A | 1.368 (4) | C2B—C7B | 1.375 (4) |
C13A—C21A | 1.434 (4) | C3B—C4B | 1.394 (4) |
C14A—C15A | 1.411 (4) | C3B—H3BA | 0.9300 |
C14A—H14B | 0.9300 | C4B—C5B | 1.379 (4) |
C15A—C16A | 1.404 (4) | C4B—H4BA | 0.9300 |
C15A—C20A | 1.406 (4) | C5B—C6B | 1.384 (4) |
C16A—C17A | 1.360 (4) | C5B—C8B | 1.481 (4) |
C16A—H16B | 0.9300 | C6B—C7B | 1.378 (4) |
C17A—C18A | 1.390 (5) | C6B—H6BA | 0.9300 |
C17A—H17B | 0.9300 | C7B—H7BA | 0.9300 |
C18A—C19A | 1.353 (5) | C8B—C9B | 1.379 (4) |
C18A—H18B | 0.9300 | C9B—C10B | 1.388 (4) |
C19A—C20A | 1.412 (4) | C9B—H9BA | 0.9300 |
C19A—H19B | 0.9300 | C10B—C13B | 1.486 (4) |
C21A—N4A | 1.397 (4) | C11B—C12B | 1.503 (4) |
C21A—N4C | 1.422 (9) | C12B—H12A | 0.9600 |
N4A—C22A | 1.461 (5) | C12B—H12B | 0.9600 |
N4A—C25A | 1.464 (5) | C12B—H12C | 0.9600 |
N5A—C26A | 1.358 (5) | C12B—H12H | 0.9600 |
N5A—C24A | 1.452 (6) | C12B—H12I | 0.9600 |
N5A—C23A | 1.461 (6) | C12B—H12J | 0.9600 |
C22A—C23A | 1.505 (4) | C13B—C14B | 1.360 (4) |
C22A—H22A | 0.9700 | C13B—C21B | 1.437 (4) |
C22A—H22B | 0.9700 | C14B—C15B | 1.413 (4) |
C23A—H23A | 0.9700 | C14B—H14A | 0.9300 |
C23A—H23B | 0.9700 | C15B—C20B | 1.395 (4) |
C24A—C25A | 1.504 (5) | C15B—C16B | 1.403 (4) |
C24A—H24A | 0.9700 | C16B—C17B | 1.362 (4) |
C24A—H24B | 0.9700 | C16B—H16A | 0.9300 |
C25A—H25A | 0.9700 | C17B—C18B | 1.387 (5) |
C25A—H25B | 0.9700 | C17B—H17A | 0.9300 |
O2A—C26A | 1.211 (5) | C18B—C19B | 1.368 (4) |
O3A—C26A | 1.332 (5) | C18B—H18A | 0.9300 |
O3A—C27A | 1.474 (5) | C19B—C20B | 1.406 (4) |
C27A—C29A | 1.509 (6) | C19B—H19A | 0.9300 |
C27A—C30A | 1.515 (9) | C22B—C23B | 1.516 (4) |
C27A—C28A | 1.516 (9) | C22B—H22C | 0.9700 |
C28A—H28D | 0.9600 | C22B—H22D | 0.9700 |
C28A—H28E | 0.9600 | C23B—H23C | 0.9700 |
C28A—H28F | 0.9600 | C23B—H23D | 0.9700 |
C29A—H29D | 0.9600 | C24B—C25B | 1.496 (4) |
C29A—H29E | 0.9600 | C24B—H24C | 0.9700 |
C29A—H29F | 0.9600 | C24B—H24D | 0.9700 |
C30A—H30D | 0.9600 | C25B—H25C | 0.9700 |
C30A—H30E | 0.9600 | C25B—H25D | 0.9700 |
C30A—H30F | 0.9600 | O2B—C26B | 1.211 (3) |
N4C—C25C | 1.464 (10) | O3B—C26B | 1.327 (4) |
N4C—C22C | 1.468 (10) | O3B—C27B | 1.466 (4) |
N5C—C26C | 1.364 (9) | C27B—C30B | 1.460 (6) |
N5C—C24C | 1.442 (10) | C27B—C28B | 1.495 (7) |
N5C—C23C | 1.474 (10) | C27B—C29B | 1.502 (6) |
C22C—C23C | 1.508 (9) | C28B—H28G | 0.9600 |
C22C—H22E | 0.9700 | C28B—H28H | 0.9600 |
C22C—H22F | 0.9700 | C28B—H28I | 0.9600 |
C23C—H23E | 0.9700 | C29B—H29G | 0.9600 |
C23C—H23F | 0.9700 | C29B—H29H | 0.9600 |
C24C—C25C | 1.504 (10) | C29B—H29I | 0.9600 |
C24C—H24E | 0.9700 | C30B—H30G | 0.9600 |
C24C—H24F | 0.9700 | C30B—H30H | 0.9600 |
C25C—H25E | 0.9700 | C30B—H30I | 0.9600 |
C25C—H25F | 0.9700 | ||
C2A—O1A—C1A | 117.2 (3) | C24C—C25C—H25F | 109.0 |
C11A—N1A—C8A | 116.4 (3) | H25E—C25C—H25F | 107.8 |
C11A—N2A—C10A | 116.2 (2) | C26C—O3C—C27C | 119.5 (11) |
C21A—N3A—C20A | 118.1 (3) | O2C—C26C—O3C | 126.0 (12) |
O1A—C1A—H1AA | 109.5 | O2C—C26C—N5C | 119.8 (11) |
O1A—C1A—H1AB | 109.5 | O3C—C26C—N5C | 113.9 (10) |
H1AA—C1A—H1AB | 109.5 | O3C—C27C—C29C | 100.6 (10) |
O1A—C1A—H1AC | 109.5 | O3C—C27C—C30C | 110.0 (12) |
H1AA—C1A—H1AC | 109.5 | C29C—C27C—C30C | 113.1 (15) |
H1AB—C1A—H1AC | 109.5 | O3C—C27C—C28C | 109.0 (11) |
C7A—C2A—O1A | 124.7 (3) | C29C—C27C—C28C | 110.5 (14) |
C7A—C2A—C3A | 119.6 (3) | C30C—C27C—C28C | 112.9 (14) |
O1A—C2A—C3A | 115.7 (3) | C27C—C28C—H28A | 109.5 |
C4A—C3A—C2A | 120.5 (3) | C27C—C28C—H28B | 109.5 |
C4A—C3A—H3AA | 119.7 | H28A—C28C—H28B | 109.5 |
C2A—C3A—H3AA | 119.7 | C27C—C28C—H28C | 109.5 |
C3A—C4A—C5A | 121.2 (3) | H28A—C28C—H28C | 109.5 |
C3A—C4A—H4AA | 119.4 | H28B—C28C—H28C | 109.5 |
C5A—C4A—H4AA | 119.4 | C27C—C29C—H29A | 109.5 |
C6A—C5A—C4A | 117.0 (3) | C27C—C29C—H29B | 109.5 |
C6A—C5A—C8A | 122.4 (3) | H29A—C29C—H29B | 109.5 |
C4A—C5A—C8A | 120.7 (3) | C27C—C29C—H29C | 109.5 |
C7A—C6A—C5A | 122.1 (3) | H29A—C29C—H29C | 109.5 |
C7A—C6A—H6AA | 119.0 | H29B—C29C—H29C | 109.5 |
C5A—C6A—H6AA | 119.0 | C27C—C30C—H30A | 109.5 |
C2A—C7A—C6A | 119.6 (3) | C27C—C30C—H30B | 109.5 |
C2A—C7A—H7AA | 120.2 | H30A—C30C—H30B | 109.5 |
C6A—C7A—H7AA | 120.2 | C27C—C30C—H30C | 109.5 |
N1A—C8A—C9A | 120.5 (2) | H30A—C30C—H30C | 109.5 |
N1A—C8A—C5A | 116.4 (2) | H30B—C30C—H30C | 109.5 |
C9A—C8A—C5A | 123.1 (3) | C2B—O1B—C1B | 117.6 (3) |
C10A—C9A—C8A | 118.7 (3) | C11B—N1B—C8B | 116.8 (3) |
C10A—C9A—H9AA | 120.7 | C11B—N2B—C10B | 116.5 (2) |
C8A—C9A—H9AA | 120.7 | C21B—N3B—C20B | 118.3 (3) |
N2A—C10A—C9A | 121.1 (3) | C21B—N4B—C22B | 117.4 (2) |
N2A—C10A—C13A | 115.1 (2) | C21B—N4B—C25B | 116.1 (2) |
C9A—C10A—C13A | 123.4 (3) | C22B—N4B—C25B | 110.0 (2) |
N2A—C11A—N1A | 127.1 (3) | C26B—N5B—C23B | 118.7 (2) |
N2A—C11A—C12A | 116.7 (3) | C26B—N5B—C24B | 121.9 (3) |
N1A—C11A—C12A | 116.2 (3) | C23B—N5B—C24B | 114.9 (2) |
C11A—C12A—H12D | 109.5 | O1B—C1B—H1BA | 109.5 |
C11A—C12A—H12E | 109.5 | O1B—C1B—H1BB | 109.5 |
H12D—C12A—H12E | 109.5 | H1BA—C1B—H1BB | 109.5 |
C11A—C12A—H12F | 109.5 | O1B—C1B—H1BC | 109.5 |
H12D—C12A—H12F | 109.5 | H1BA—C1B—H1BC | 109.5 |
H12E—C12A—H12F | 109.5 | H1BB—C1B—H1BC | 109.5 |
C11A—C12A—H12X | 109.5 | C3B—C2B—O1B | 124.4 (3) |
H12D—C12A—H12X | 141.1 | C3B—C2B—C7B | 120.3 (3) |
H12E—C12A—H12X | 56.3 | O1B—C2B—C7B | 115.3 (3) |
H12F—C12A—H12X | 56.3 | C2B—C3B—C4B | 119.3 (3) |
C11A—C12A—H12Y | 109.5 | C2B—C3B—H3BA | 120.3 |
H12D—C12A—H12Y | 56.3 | C4B—C3B—H3BA | 120.3 |
H12E—C12A—H12Y | 141.1 | C5B—C4B—C3B | 121.5 (3) |
H12F—C12A—H12Y | 56.3 | C5B—C4B—H4BA | 119.2 |
H12X—C12A—H12Y | 109.5 | C3B—C4B—H4BA | 119.2 |
C11A—C12A—H12Z | 109.5 | C4B—C5B—C6B | 117.4 (3) |
H12D—C12A—H12Z | 56.3 | C4B—C5B—C8B | 121.4 (3) |
H12E—C12A—H12Z | 56.3 | C6B—C5B—C8B | 121.2 (3) |
H12F—C12A—H12Z | 141.1 | C7B—C6B—C5B | 121.6 (3) |
H12X—C12A—H12Z | 109.5 | C7B—C6B—H6BA | 119.2 |
H12Y—C12A—H12Z | 109.5 | C5B—C6B—H6BA | 119.2 |
C14A—C13A—C21A | 116.9 (3) | C2B—C7B—C6B | 119.7 (3) |
C14A—C13A—C10A | 117.3 (3) | C2B—C7B—H7BA | 120.1 |
C21A—C13A—C10A | 125.5 (2) | C6B—C7B—H7BA | 120.1 |
C13A—C14A—C15A | 121.8 (3) | N1B—C8B—C9B | 120.4 (3) |
C13A—C14A—H14B | 119.1 | N1B—C8B—C5B | 116.2 (3) |
C15A—C14A—H14B | 119.1 | C9B—C8B—C5B | 123.3 (2) |
C16A—C15A—C20A | 119.9 (3) | C8B—C9B—C10B | 118.7 (3) |
C16A—C15A—C14A | 123.9 (3) | C8B—C9B—H9BA | 120.6 |
C20A—C15A—C14A | 116.2 (3) | C10B—C9B—H9BA | 120.6 |
C17A—C16A—C15A | 121.2 (4) | N2B—C10B—C9B | 121.1 (3) |
C17A—C16A—H16B | 119.4 | N2B—C10B—C13B | 116.5 (2) |
C15A—C16A—H16B | 119.4 | C9B—C10B—C13B | 122.2 (3) |
C16A—C17A—C18A | 118.6 (3) | N2B—C11B—N1B | 126.4 (3) |
C16A—C17A—H17B | 120.7 | N2B—C11B—C12B | 116.8 (3) |
C18A—C17A—H17B | 120.7 | N1B—C11B—C12B | 116.8 (3) |
C19A—C18A—C17A | 122.1 (4) | C11B—C12B—H12A | 109.5 |
C19A—C18A—H18B | 118.9 | C11B—C12B—H12B | 109.5 |
C17A—C18A—H18B | 118.9 | H12A—C12B—H12B | 109.5 |
C18A—C19A—C20A | 120.5 (4) | C11B—C12B—H12C | 109.5 |
C18A—C19A—H19B | 119.7 | H12A—C12B—H12C | 109.5 |
C20A—C19A—H19B | 119.7 | H12B—C12B—H12C | 109.5 |
N3A—C20A—C15A | 123.1 (3) | C11B—C12B—H12H | 109.5 |
N3A—C20A—C19A | 119.2 (3) | H12A—C12B—H12H | 141.1 |
C15A—C20A—C19A | 117.6 (3) | H12B—C12B—H12H | 56.3 |
N3A—C21A—N4A | 115.7 (4) | H12C—C12B—H12H | 56.3 |
N3A—C21A—N4C | 122.0 (13) | C11B—C12B—H12I | 109.5 |
N3A—C21A—C13A | 123.2 (3) | H12A—C12B—H12I | 56.3 |
N4A—C21A—C13A | 121.0 (4) | H12B—C12B—H12I | 141.1 |
N4C—C21A—C13A | 114.5 (12) | H12C—C12B—H12I | 56.3 |
C21A—N4A—C22A | 114.4 (5) | H12H—C12B—H12I | 109.5 |
C21A—N4A—C25A | 116.2 (5) | C11B—C12B—H12J | 109.5 |
C22A—N4A—C25A | 109.8 (4) | H12A—C12B—H12J | 56.3 |
C26A—N5A—C24A | 118.7 (4) | H12B—C12B—H12J | 56.3 |
C26A—N5A—C23A | 124.3 (4) | H12C—C12B—H12J | 141.1 |
C24A—N5A—C23A | 114.2 (3) | H12H—C12B—H12J | 109.5 |
N4A—C22A—C23A | 111.3 (4) | H12I—C12B—H12J | 109.5 |
N4A—C22A—H22A | 109.4 | C14B—C13B—C21B | 116.9 (3) |
C23A—C22A—H22A | 109.4 | C14B—C13B—C10B | 118.3 (3) |
N4A—C22A—H22B | 109.4 | C21B—C13B—C10B | 124.6 (3) |
C23A—C22A—H22B | 109.4 | C13B—C14B—C15B | 121.7 (3) |
H22A—C22A—H22B | 108.0 | C13B—C14B—H14A | 119.1 |
N5A—C23A—C22A | 109.9 (4) | C15B—C14B—H14A | 119.1 |
N5A—C23A—H23A | 109.7 | C20B—C15B—C16B | 120.3 (3) |
C22A—C23A—H23A | 109.7 | C20B—C15B—C14B | 116.7 (3) |
N5A—C23A—H23B | 109.7 | C16B—C15B—C14B | 123.0 (3) |
C22A—C23A—H23B | 109.7 | C17B—C16B—C15B | 119.8 (3) |
H23A—C23A—H23B | 108.2 | C17B—C16B—H16A | 120.1 |
N5A—C24A—C25A | 110.7 (4) | C15B—C16B—H16A | 120.1 |
N5A—C24A—H24A | 109.5 | C16B—C17B—C18B | 120.3 (3) |
C25A—C24A—H24A | 109.5 | C16B—C17B—H17A | 119.9 |
N5A—C24A—H24B | 109.5 | C18B—C17B—H17A | 119.9 |
C25A—C24A—H24B | 109.5 | C19B—C18B—C17B | 121.0 (4) |
H24A—C24A—H24B | 108.1 | C19B—C18B—H18A | 119.5 |
N4A—C25A—C24A | 109.0 (4) | C17B—C18B—H18A | 119.5 |
N4A—C25A—H25A | 109.9 | C18B—C19B—C20B | 120.0 (3) |
C24A—C25A—H25A | 109.9 | C18B—C19B—H19A | 120.0 |
N4A—C25A—H25B | 109.9 | C20B—C19B—H19A | 120.0 |
C24A—C25A—H25B | 109.9 | N3B—C20B—C15B | 122.7 (3) |
H25A—C25A—H25B | 108.3 | N3B—C20B—C19B | 118.6 (3) |
C26A—O3A—C27A | 120.1 (4) | C15B—C20B—C19B | 118.7 (3) |
O2A—C26A—O3A | 125.9 (4) | N3B—C21B—N4B | 117.5 (3) |
O2A—C26A—N5A | 123.2 (4) | N3B—C21B—C13B | 123.2 (3) |
O3A—C26A—N5A | 110.9 (4) | N4B—C21B—C13B | 119.2 (3) |
O3A—C27A—C29A | 101.2 (4) | N4B—C22B—C23B | 109.1 (3) |
O3A—C27A—C30A | 109.8 (4) | N4B—C22B—H22C | 109.9 |
C29A—C27A—C30A | 111.7 (6) | C23B—C22B—H22C | 109.9 |
O3A—C27A—C28A | 110.4 (5) | N4B—C22B—H22D | 109.9 |
C29A—C27A—C28A | 110.7 (6) | C23B—C22B—H22D | 109.9 |
C30A—C27A—C28A | 112.5 (6) | H22C—C22B—H22D | 108.3 |
C27A—C28A—H28D | 109.5 | N5B—C23B—C22B | 110.7 (2) |
C27A—C28A—H28E | 109.5 | N5B—C23B—H23C | 109.5 |
H28D—C28A—H28E | 109.5 | C22B—C23B—H23C | 109.5 |
C27A—C28A—H28F | 109.5 | N5B—C23B—H23D | 109.5 |
H28D—C28A—H28F | 109.5 | C22B—C23B—H23D | 109.5 |
H28E—C28A—H28F | 109.5 | H23C—C23B—H23D | 108.1 |
C27A—C29A—H29D | 109.5 | N5B—C24B—C25B | 110.4 (3) |
C27A—C29A—H29E | 109.5 | N5B—C24B—H24C | 109.6 |
H29D—C29A—H29E | 109.5 | C25B—C24B—H24C | 109.6 |
C27A—C29A—H29F | 109.5 | N5B—C24B—H24D | 109.6 |
H29D—C29A—H29F | 109.5 | C25B—C24B—H24D | 109.6 |
H29E—C29A—H29F | 109.5 | H24C—C24B—H24D | 108.1 |
C27A—C30A—H30D | 109.5 | N4B—C25B—C24B | 110.4 (2) |
C27A—C30A—H30E | 109.5 | N4B—C25B—H25C | 109.6 |
H30D—C30A—H30E | 109.5 | C24B—C25B—H25C | 109.6 |
C27A—C30A—H30F | 109.5 | N4B—C25B—H25D | 109.6 |
H30D—C30A—H30F | 109.5 | C24B—C25B—H25D | 109.6 |
H30E—C30A—H30F | 109.5 | H25C—C25B—H25D | 108.1 |
C21A—N4C—C25C | 119.0 (17) | C26B—O3B—C27B | 122.9 (3) |
C21A—N4C—C22C | 119.2 (17) | O2B—C26B—O3B | 124.8 (3) |
C25C—N4C—C22C | 108.6 (12) | O2B—C26B—N5B | 123.2 (3) |
C26C—N5C—C24C | 123.0 (11) | O3B—C26B—N5B | 112.0 (3) |
C26C—N5C—C23C | 120.0 (11) | C30B—C27B—O3B | 112.3 (4) |
C24C—N5C—C23C | 111.6 (11) | C30B—C27B—C28B | 110.3 (5) |
N4C—C22C—C23C | 112.8 (12) | O3B—C27B—C28B | 107.3 (4) |
N4C—C22C—H22E | 109.0 | C30B—C27B—C29B | 112.9 (5) |
C23C—C22C—H22E | 109.0 | O3B—C27B—C29B | 102.1 (3) |
N4C—C22C—H22F | 109.0 | C28B—C27B—C29B | 111.7 (5) |
C23C—C22C—H22F | 109.0 | C27B—C28B—H28G | 109.5 |
H22E—C22C—H22F | 107.8 | C27B—C28B—H28H | 109.5 |
N5C—C23C—C22C | 109.2 (12) | H28G—C28B—H28H | 109.5 |
N5C—C23C—H23E | 109.8 | C27B—C28B—H28I | 109.5 |
C22C—C23C—H23E | 109.8 | H28G—C28B—H28I | 109.5 |
N5C—C23C—H23F | 109.8 | H28H—C28B—H28I | 109.5 |
C22C—C23C—H23F | 109.8 | C27B—C29B—H29G | 109.5 |
H23E—C23C—H23F | 108.3 | C27B—C29B—H29H | 109.5 |
N5C—C24C—C25C | 111.2 (12) | H29G—C29B—H29H | 109.5 |
N5C—C24C—H24E | 109.4 | C27B—C29B—H29I | 109.5 |
C25C—C24C—H24E | 109.4 | H29G—C29B—H29I | 109.5 |
N5C—C24C—H24F | 109.4 | H29H—C29B—H29I | 109.5 |
C25C—C24C—H24F | 109.4 | C27B—C30B—H30G | 109.5 |
H24E—C24C—H24F | 108.0 | C27B—C30B—H30H | 109.5 |
N4C—C25C—C24C | 113.0 (12) | H30G—C30B—H30H | 109.5 |
N4C—C25C—H25E | 109.0 | C27B—C30B—H30I | 109.5 |
C24C—C25C—H25E | 109.0 | H30G—C30B—H30I | 109.5 |
N4C—C25C—H25F | 109.0 | H30H—C30B—H30I | 109.5 |
C1A—O1A—C2A—C7A | −3.2 (5) | C23C—N5C—C24C—C25C | 55 (2) |
C1A—O1A—C2A—C3A | 176.0 (3) | C21A—N4C—C25C—C24C | −165 (3) |
C7A—C2A—C3A—C4A | 0.1 (5) | C22C—N4C—C25C—C24C | 54 (2) |
O1A—C2A—C3A—C4A | −179.2 (3) | N5C—C24C—C25C—N4C | −55 (2) |
C2A—C3A—C4A—C5A | 0.1 (5) | C27C—O3C—C26C—O2C | −2 (3) |
C3A—C4A—C5A—C6A | 0.0 (4) | C27C—O3C—C26C—N5C | 171.3 (17) |
C3A—C4A—C5A—C8A | 179.8 (3) | C24C—N5C—C26C—O2C | −170 (2) |
C4A—C5A—C6A—C7A | −0.4 (4) | C23C—N5C—C26C—O2C | −18 (3) |
C8A—C5A—C6A—C7A | 179.8 (3) | C24C—N5C—C26C—O3C | 16 (3) |
O1A—C2A—C7A—C6A | 178.8 (3) | C23C—N5C—C26C—O3C | 168.1 (19) |
C3A—C2A—C7A—C6A | −0.4 (5) | C26C—O3C—C27C—C29C | −176.8 (17) |
C5A—C6A—C7A—C2A | 0.5 (5) | C26C—O3C—C27C—C30C | 64 (2) |
C11A—N1A—C8A—C9A | −1.7 (4) | C26C—O3C—C27C—C28C | −61 (2) |
C11A—N1A—C8A—C5A | 179.9 (2) | C1B—O1B—C2B—C3B | −2.6 (5) |
C6A—C5A—C8A—N1A | −160.9 (3) | C1B—O1B—C2B—C7B | 178.5 (3) |
C4A—C5A—C8A—N1A | 19.3 (4) | O1B—C2B—C3B—C4B | 178.6 (3) |
C6A—C5A—C8A—C9A | 20.8 (4) | C7B—C2B—C3B—C4B | −2.7 (5) |
C4A—C5A—C8A—C9A | −159.0 (3) | C2B—C3B—C4B—C5B | −1.0 (5) |
N1A—C8A—C9A—C10A | 1.1 (4) | C3B—C4B—C5B—C6B | 3.7 (5) |
C5A—C8A—C9A—C10A | 179.4 (2) | C3B—C4B—C5B—C8B | −174.0 (3) |
C11A—N2A—C10A—C9A | −0.6 (4) | C4B—C5B—C6B—C7B | −2.9 (4) |
C11A—N2A—C10A—C13A | 172.7 (2) | C8B—C5B—C6B—C7B | 174.9 (3) |
C8A—C9A—C10A—N2A | 0.1 (4) | C3B—C2B—C7B—C6B | 3.5 (5) |
C8A—C9A—C10A—C13A | −172.7 (2) | O1B—C2B—C7B—C6B | −177.6 (3) |
C10A—N2A—C11A—N1A | 0.0 (5) | C5B—C6B—C7B—C2B | −0.7 (5) |
C10A—N2A—C11A—C12A | −178.7 (3) | C11B—N1B—C8B—C9B | −1.0 (4) |
C8A—N1A—C11A—N2A | 1.2 (5) | C11B—N1B—C8B—C5B | −178.9 (3) |
C8A—N1A—C11A—C12A | 179.9 (3) | C4B—C5B—C8B—N1B | −174.6 (3) |
N2A—C10A—C13A—C14A | −29.4 (4) | C6B—C5B—C8B—N1B | 7.8 (4) |
C9A—C10A—C13A—C14A | 143.8 (3) | C4B—C5B—C8B—C9B | 7.6 (4) |
N2A—C10A—C13A—C21A | 157.0 (3) | C6B—C5B—C8B—C9B | −170.1 (3) |
C9A—C10A—C13A—C21A | −29.9 (4) | N1B—C8B—C9B—C10B | 1.9 (4) |
C21A—C13A—C14A—C15A | 2.8 (4) | C5B—C8B—C9B—C10B | 179.7 (3) |
C10A—C13A—C14A—C15A | −171.5 (2) | C11B—N2B—C10B—C9B | 0.3 (4) |
C13A—C14A—C15A—C16A | −176.7 (3) | C11B—N2B—C10B—C13B | 174.7 (3) |
C13A—C14A—C15A—C20A | 4.0 (4) | C8B—C9B—C10B—N2B | −1.6 (4) |
C20A—C15A—C16A—C17A | 0.1 (4) | C8B—C9B—C10B—C13B | −175.6 (2) |
C14A—C15A—C16A—C17A | −179.2 (3) | C10B—N2B—C11B—N1B | 0.7 (5) |
C15A—C16A—C17A—C18A | 2.2 (5) | C10B—N2B—C11B—C12B | −179.2 (3) |
C16A—C17A—C18A—C19A | −2.0 (5) | C8B—N1B—C11B—N2B | −0.4 (5) |
C17A—C18A—C19A—C20A | −0.5 (5) | C8B—N1B—C11B—C12B | 179.6 (3) |
C21A—N3A—C20A—C15A | 3.1 (4) | N2B—C10B—C13B—C14B | −37.4 (4) |
C21A—N3A—C20A—C19A | 179.1 (3) | C9B—C10B—C13B—C14B | 136.9 (3) |
C16A—C15A—C20A—N3A | 173.4 (3) | N2B—C10B—C13B—C21B | 148.4 (3) |
C14A—C15A—C20A—N3A | −7.2 (4) | C9B—C10B—C13B—C21B | −37.4 (4) |
C16A—C15A—C20A—C19A | −2.6 (4) | C21B—C13B—C14B—C15B | 3.9 (4) |
C14A—C15A—C20A—C19A | 176.8 (3) | C10B—C13B—C14B—C15B | −170.8 (2) |
C18A—C19A—C20A—N3A | −173.4 (3) | C13B—C14B—C15B—C20B | 2.4 (4) |
C18A—C19A—C20A—C15A | 2.8 (4) | C13B—C14B—C15B—C16B | −179.5 (3) |
C20A—N3A—C21A—N4A | −176.8 (4) | C20B—C15B—C16B—C17B | −0.3 (5) |
C20A—N3A—C21A—N4C | −168.5 (17) | C14B—C15B—C16B—C17B | −178.2 (3) |
C20A—N3A—C21A—C13A | 4.4 (4) | C15B—C16B—C17B—C18B | 1.7 (5) |
C14A—C13A—C21A—N3A | −7.3 (4) | C16B—C17B—C18B—C19B | −1.4 (5) |
C10A—C13A—C21A—N3A | 166.4 (2) | C17B—C18B—C19B—C20B | −0.2 (5) |
C14A—C13A—C21A—N4A | 173.9 (4) | C21B—N3B—C20B—C15B | 3.7 (4) |
C10A—C13A—C21A—N4A | −12.4 (6) | C21B—N3B—C20B—C19B | −179.6 (3) |
C14A—C13A—C21A—N4C | 166.0 (16) | C16B—C15B—C20B—N3B | 175.4 (3) |
C10A—C13A—C21A—N4C | −20.3 (17) | C14B—C15B—C20B—N3B | −6.5 (4) |
N3A—C21A—N4A—C22A | 119.7 (5) | C16B—C15B—C20B—C19B | −1.3 (4) |
C13A—C21A—N4A—C22A | −61.4 (6) | C14B—C15B—C20B—C19B | 176.8 (3) |
N3A—C21A—N4A—C25A | −9.8 (7) | C18B—C19B—C20B—N3B | −175.3 (3) |
C13A—C21A—N4A—C25A | 169.0 (4) | C18B—C19B—C20B—C15B | 1.6 (5) |
C21A—N4A—C22A—C23A | 167.0 (6) | C20B—N3B—C21B—N4B | −177.9 (2) |
C25A—N4A—C22A—C23A | −60.2 (6) | C20B—N3B—C21B—C13B | 3.3 (4) |
C26A—N5A—C23A—C22A | 147.7 (5) | C22B—N4B—C21B—N3B | −9.6 (4) |
C24A—N5A—C23A—C22A | −51.5 (5) | C25B—N4B—C21B—N3B | 123.5 (3) |
N4A—C22A—C23A—N5A | 54.0 (6) | C22B—N4B—C21B—C13B | 169.3 (2) |
C26A—N5A—C24A—C25A | −144.1 (4) | C25B—N4B—C21B—C13B | −57.7 (3) |
C23A—N5A—C24A—C25A | 54.0 (5) | C14B—C13B—C21B—N3B | −7.0 (4) |
C21A—N4A—C25A—C24A | −167.2 (6) | C10B—C13B—C21B—N3B | 167.3 (2) |
C22A—N4A—C25A—C24A | 61.0 (5) | C14B—C13B—C21B—N4B | 174.1 (2) |
N5A—C24A—C25A—N4A | −57.5 (5) | C10B—C13B—C21B—N4B | −11.5 (4) |
C27A—O3A—C26A—O2A | 4.9 (6) | C21B—N4B—C22B—C23B | −162.8 (2) |
C27A—O3A—C26A—N5A | −175.2 (4) | C25B—N4B—C22B—C23B | 61.5 (3) |
C24A—N5A—C26A—O2A | 8.5 (6) | C26B—N5B—C23B—C22B | −152.0 (3) |
C23A—N5A—C26A—O2A | 168.5 (4) | C24B—N5B—C23B—C22B | 51.4 (4) |
C24A—N5A—C26A—O3A | −171.4 (3) | N4B—C22B—C23B—N5B | −55.4 (4) |
C23A—N5A—C26A—O3A | −11.4 (6) | C26B—N5B—C24B—C25B | 153.4 (3) |
C26A—O3A—C27A—C29A | 176.5 (4) | C23B—N5B—C24B—C25B | −50.8 (4) |
C26A—O3A—C27A—C30A | −65.3 (6) | C21B—N4B—C25B—C24B | 161.7 (3) |
C26A—O3A—C27A—C28A | 59.2 (7) | C22B—N4B—C25B—C24B | −61.9 (3) |
N3A—C21A—N4C—C25C | −15 (3) | N5B—C24B—C25B—N4B | 54.8 (4) |
C13A—C21A—N4C—C25C | 171.5 (19) | C27B—O3B—C26B—O2B | 3.2 (6) |
N3A—C21A—N4C—C22C | 121 (2) | C27B—O3B—C26B—N5B | −176.7 (3) |
C13A—C21A—N4C—C22C | −52 (3) | C23B—N5B—C26B—O2B | 13.4 (5) |
C21A—N4C—C22C—C23C | 163 (3) | C24B—N5B—C26B—O2B | 168.3 (3) |
C25C—N4C—C22C—C23C | −56 (2) | C23B—N5B—C26B—O3B | −166.7 (3) |
C26C—N5C—C23C—C22C | 149 (2) | C24B—N5B—C26B—O3B | −11.8 (5) |
C24C—N5C—C23C—C22C | −56 (2) | C26B—O3B—C27B—C30B | −57.1 (6) |
N4C—C22C—C23C—N5C | 58 (2) | C26B—O3B—C27B—C28B | 64.2 (5) |
C26C—N5C—C24C—C25C | −151 (2) | C26B—O3B—C27B—C29B | −178.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7B—H7BA···O2Bi | 0.93 | 2.40 | 3.141 (2) | 136 |
Symmetry code: (i) x+1, y, z. |
Funding information
Funding for this research was provided by: Indian Council of Medical Research (grant No. BIC/12(14)/2012 to RK); Department of Science and Technology (grant No. EMR/2014/000467 to RK; award No. SR/S2/CMP-47/2003). RK also acknowledges the Department of Science & Technology for a single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.
References
Campbell, S. F., Hardstone, J. D. & Palmer, M. J. (1988). J. Med. Chem. 31, 1031–1035. CrossRef CAS PubMed Web of Science Google Scholar
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jain, K. S., Chitre, T. S., Miniyar, P. B., Kathiravan, M. K., Bendre, V. S., Veer, V. S., Shahane, S. R. & Shishoo, C. J. (2006). Curr. Sci. 90, 793–803. CAS Google Scholar
Kalluraya, B. & Sreenivasa, S. (1998). Farmaco, 53, 399–404. Web of Science CrossRef CAS PubMed Google Scholar
Khanage, S. G., Raju, S. A., Mohite, P. B. & Pandhare, R. B. (2012). Adv. Pharma. Bull. 2, 213–222. Google Scholar
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324–326. CrossRef CAS PubMed Web of Science Google Scholar
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o796–o797. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Prasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110. Web of Science CSD CrossRef IUCr Journals Google Scholar
Selvam, T. P., James, C. R., Dniandev, P. V. & Valzita, S. K. (2012). Res. Pharm. 2, 1–9. Google Scholar
Sharma, D. K., Desai, N. R., Sreenivasa, S., Anthal, S. & Kant, R. (2017). IUCrData, 2, x171600. 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. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Singh, V. D., Anthal, S., Desai, N. R., Arunakumar, D. B., Sreenivasa, S., Kamni & Kant, R. (2018). IUCr Data 3, x180030. 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.