organic compounds
Dimethyl 3,3′-[(4-nitrophenyl)methylene]bis(1H-indole-2-carboxylate) ethanol hemisolvate
aTargeted MRI Contrast Agents Laboratory of Jiangsu Province, Nanjing Polytechnic Institute, Nanjing 210048, People's Republic of China, and bCollege of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, People's Republic of China
*Correspondence e-mail: njutshs@126.com
There are two main molecules in 27H21N3O6·0.5C2H5OH. In both, the indole ring systems are approximately perpendicular to each other, at dihedral angles of 69.3 (5) and 82.8(4)°. In the crystal, molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional supramolecular architecture. The solvent ethanol molecule acts as a donor, forming an O—H⋯O hydrogen bond, reinforcing the structure.
of the title compound, CKeywords: crystal structure; bisindole; MRI; contrast agents.
CCDC reference: 2056440
Structure description
There are abundant bis(indolyl)methane derivatives in various terrestrial and marine natural resources (Sundberg, 1996). They can be used as precursors for MRI necrosis avid contrast agents (Ni, 2008). As part of our ongoing studies of bis(indoyl)methane compounds, we now report the synthesis and of the title bis(indoly)methane compound.
The molecular structure of the title compound is shown in Fig. 1. In the first bisindole molhe two indole ring systems are nearly perpendicular to one another [dihedral angle = 69.3 (5)°] while the benzene ring (C2–C7) is twisted to the N2/C8–C15 and N3/C18–C25 indole ring systems by dihedral angles of 44.3 (3) and 77.6 (4)°, respectively. The carboxyl groups are approximately co-planar with the attached indole ring systems, the dihedral angles between the carboxyl groups and the mean plane of the N2/C8–C15 and N3/C18–C25 indole ring systems being 20.7 (4) and 3.8 (5)°, respectively. For the second bisindole molecule, the two indole ring systems are also nearly perpendicular to one another [dihedral angle = 82.8 (4)°] while the benzene ring (C29–C34) is twisted to the N5/C35–C42 and N6/C45–C52 indole ring systems with dihedral angles of 88.5 (5) and 81.8 (4)°, respectively.
In the crystal, molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional supramolecular architecture. The solvent ethanol molecule acts as a donor, forming an O—H⋯O hydrogen bond, reinforcing the structure (Table 1, Fig. 2).
Several similar structures have been reported previously, viz. diethyl 3,3′-(phenylmethylene)bis(1H-indole-2-carboxylate) (Sun et al., 2012), dimethyl 3,3′-[(3-nitrophenyl)methylene]bis(1H-indole-2-carboxylate) ethanol monosolvate (Sun et al., 2014), diethyl 3,3′-[(4-nitrophenyl)methylene]bis(1H-indole-2-carboxylate) (Sun et al., 2017) and diethyl 3,3′-[(3-fluorophenyl)methylene]bis(1H-indole-2-carboxylate) (Jiang et al., 2020). In these structures, the indole ring systems are also nearly perpendicular to one another, making dihedral angles of 82.0 (5), 89.3 (5), 89.7 (5) and 88.3 (4)°, respectively.
Synthesis and crystallization
Methyl indole-2-carboxylate (1.75 g, 10 mmol) was dissolved in 20 ml of ethanol, and 4-nitrobenzaldehyde (0.76 g, 5 mmol) and concentrated HCl (0.5 ml) were added and the mixture was heated to reflux temperature for 2 h. After cooling, the white product was filtered off and washed thoroughly with ethanol. The reaction was monitored by TLC (AcOEt: hexane = 1:3). Yield 90%. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 2056440
https://doi.org/10.1107/S2414314621000572/xu4043sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621000572/xu4043Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314621000572/xu4043Isup3.cml
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).2C27H21N3O6·C2H6O | F(000) = 2120 |
Mr = 1013.00 | Dx = 1.326 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.248 (4) Å | Cell parameters from 25 reflections |
b = 10.304 (2) Å | θ = 9–12° |
c = 27.541 (6) Å | µ = 0.10 mm−1 |
β = 101.41 (3)° | T = 293 K |
V = 5076.1 (18) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 9324 independent reflections |
Radiation source: fine-focus sealed tube | 4039 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.160 |
ω scans | θmax = 25.4°, θmin = 1.1° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→22 |
Tmin = 0.97, Tmax = 0.98 | k = 0→12 |
9324 measured reflections | l = −33→32 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.104 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.213 | H-atom parameters constrained |
S = 1.20 | w = 1/[σ2(Fo2) + (0.050P)2 + 2.P] where P = (Fo2 + 2Fc2)/3 |
9324 reflections | (Δ/σ)max < 0.001 |
676 parameters | Δρmax = 0.36 e Å−3 |
2 restraints | Δρmin = −0.28 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.9831 (3) | 0.9393 (4) | 0.14010 (17) | 0.0539 (13) | |
H2A | 1.0127 | 1.0046 | 0.1411 | 0.065* | |
C1 | 0.9320 (3) | 0.5961 (5) | 0.11280 (19) | 0.0408 (14) | |
H1A | 0.9837 | 0.5646 | 0.1190 | 0.049* | |
N1 | 0.7905 (4) | 0.3205 (6) | 0.2503 (2) | 0.0752 (17) | |
O1 | 0.8245 (4) | 0.3088 (7) | 0.2916 (2) | 0.147 (3) | |
C2 | 0.8937 (3) | 0.5178 (5) | 0.1471 (2) | 0.0406 (13) | |
O2 | 0.7277 (3) | 0.2809 (5) | 0.23639 (18) | 0.0842 (15) | |
O3 | 1.1030 (2) | 0.8945 (4) | 0.10153 (16) | 0.0692 (13) | |
N3 | 0.8863 (2) | 0.4737 (4) | −0.01617 (16) | 0.0488 (12) | |
H3A | 0.8903 | 0.4179 | −0.0387 | 0.059* | |
C3 | 0.9289 (3) | 0.5036 (6) | 0.1954 (2) | 0.0576 (16) | |
H3B | 0.9762 | 0.5396 | 0.2055 | 0.069* | |
N4 | 0.6521 (4) | 0.5750 (8) | 0.2207 (3) | 0.092 (2) | |
O4 | 1.0854 (2) | 0.6789 (4) | 0.09867 (14) | 0.0573 (11) | |
C4 | 0.8975 (4) | 0.4384 (6) | 0.2296 (2) | 0.0641 (18) | |
H4A | 0.9227 | 0.4296 | 0.2623 | 0.077* | |
O5 | 0.9967 (2) | 0.3403 (4) | 0.09448 (16) | 0.0741 (14) | |
C5 | 0.8273 (4) | 0.3867 (6) | 0.2139 (2) | 0.0556 (17) | |
N5 | 0.5897 (2) | 0.5494 (4) | 0.49143 (17) | 0.0487 (12) | |
H5A | 0.5850 | 0.6178 | 0.5085 | 0.058* | |
O6 | 0.9745 (2) | 0.2731 (3) | 0.01570 (14) | 0.0635 (12) | |
C6 | 0.7899 (3) | 0.3955 (5) | 0.1665 (2) | 0.0551 (17) | |
H6A | 0.7425 | 0.3595 | 0.1567 | 0.066* | |
N6 | 0.5217 (3) | −0.0105 (4) | 0.39919 (18) | 0.0523 (13) | |
H6B | 0.5035 | −0.0759 | 0.4122 | 0.063* | |
O7 | 0.7097 (4) | 0.6377 (6) | 0.2306 (2) | 0.124 (2) | |
C7 | 0.8245 (3) | 0.4602 (6) | 0.1328 (2) | 0.0568 (16) | |
H7A | 0.8004 | 0.4647 | 0.0998 | 0.068* | |
O8 | 0.6225 (3) | 0.5476 (8) | 0.1784 (2) | 0.158 (3) | |
C8 | 0.9376 (3) | 0.7386 (5) | 0.12664 (18) | 0.0400 (13) | |
C9 | 0.8841 (3) | 0.8163 (5) | 0.14583 (18) | 0.0410 (14) | |
O9 | 0.4550 (2) | 0.5844 (4) | 0.37946 (17) | 0.0687 (13) | |
O10 | 0.4921 (2) | 0.7300 (4) | 0.43938 (17) | 0.0739 (13) | |
C10 | 0.8120 (3) | 0.7974 (6) | 0.1546 (2) | 0.0534 (16) | |
H10A | 0.7893 | 0.7165 | 0.1491 | 0.064* | |
C11 | 0.7748 (3) | 0.8978 (6) | 0.1714 (2) | 0.0627 (18) | |
H11A | 0.7269 | 0.8847 | 0.1773 | 0.075* | |
O11 | 0.4208 (2) | 0.0506 (4) | 0.45411 (17) | 0.0748 (14) | |
C12 | 0.8081 (4) | 1.0198 (6) | 0.1798 (2) | 0.071 (2) | |
H12A | 0.7821 | 1.0868 | 0.1915 | 0.085* | |
O12 | 0.4222 (2) | 0.2619 (4) | 0.43498 (14) | 0.0587 (11) | |
C13 | 0.8771 (4) | 1.0426 (6) | 0.1712 (2) | 0.0601 (18) | |
H13A | 0.8990 | 1.1240 | 0.1771 | 0.072* | |
O13 | 1.0623 (4) | 0.1713 (5) | 0.1666 (2) | 0.146 (3) | |
H13B | 1.0436 | 0.2240 | 0.1454 | 0.219* | |
C14 | 0.9146 (3) | 0.9412 (5) | 0.1535 (2) | 0.0476 (15) | |
C15 | 0.9967 (3) | 0.8174 (5) | 0.12499 (19) | 0.0434 (14) | |
C16 | 1.0642 (3) | 0.7862 (6) | 0.1073 (2) | 0.0462 (15) | |
C17 | 1.1726 (3) | 0.8759 (7) | 0.0856 (3) | 0.096 (3) | |
H17A | 1.1956 | 0.9586 | 0.0827 | 0.144* | |
H17B | 1.2053 | 0.8236 | 0.1094 | 0.144* | |
H17C | 1.1635 | 0.8331 | 0.0540 | 0.144* | |
C18 | 0.9023 (3) | 0.5722 (5) | 0.05790 (18) | 0.0379 (13) | |
C19 | 0.8530 (3) | 0.6490 (5) | 0.02260 (19) | 0.0415 (14) | |
C20 | 0.8157 (3) | 0.7670 (5) | 0.0226 (2) | 0.0546 (16) | |
H20A | 0.8200 | 0.8140 | 0.0519 | 0.066* | |
C21 | 0.7729 (3) | 0.8144 (6) | −0.0200 (2) | 0.0617 (18) | |
H21A | 0.7488 | 0.8937 | −0.0194 | 0.074* | |
C22 | 0.7647 (3) | 0.7462 (6) | −0.0643 (2) | 0.0653 (18) | |
H22A | 0.7348 | 0.7804 | −0.0927 | 0.078* | |
C23 | 0.8000 (3) | 0.6288 (6) | −0.0669 (2) | 0.0634 (18) | |
H23A | 0.7940 | 0.5819 | −0.0963 | 0.076* | |
C24 | 0.8455 (3) | 0.5837 (5) | −0.0231 (2) | 0.0448 (14) | |
C25 | 0.9202 (3) | 0.4655 (5) | 0.0326 (2) | 0.0436 (14) | |
C26 | 0.9679 (3) | 0.3557 (5) | 0.0517 (2) | 0.0478 (15) | |
C27 | 1.0198 (4) | 0.1602 (5) | 0.0313 (2) | 0.076 (2) | |
H27A | 1.0215 | 0.1064 | 0.0031 | 0.115* | |
H27B | 1.0696 | 0.1870 | 0.0462 | 0.115* | |
H27C | 0.9985 | 0.1121 | 0.0550 | 0.115* | |
C28 | 0.5378 (3) | 0.3441 (5) | 0.3791 (2) | 0.0435 (14) | |
H28A | 0.4841 | 0.3632 | 0.3725 | 0.052* | |
C29 | 0.5678 (3) | 0.4072 (5) | 0.3375 (2) | 0.0425 (14) | |
C30 | 0.5284 (3) | 0.4046 (6) | 0.2900 (2) | 0.0698 (19) | |
H30A | 0.4821 | 0.3636 | 0.2835 | 0.084* | |
C31 | 0.5543 (4) | 0.4603 (8) | 0.2512 (2) | 0.081 (2) | |
H31A | 0.5262 | 0.4576 | 0.2191 | 0.097* | |
C32 | 0.6227 (4) | 0.5199 (6) | 0.2613 (2) | 0.0579 (17) | |
C33 | 0.6644 (3) | 0.5235 (5) | 0.3077 (2) | 0.0572 (17) | |
H33A | 0.7113 | 0.5624 | 0.3138 | 0.069* | |
C34 | 0.6364 (3) | 0.4690 (5) | 0.3455 (2) | 0.0550 (16) | |
H34A | 0.6644 | 0.4736 | 0.3776 | 0.066* | |
C35 | 0.5697 (3) | 0.4046 (5) | 0.4289 (2) | 0.0424 (14) | |
C36 | 0.6299 (3) | 0.3608 (5) | 0.4667 (2) | 0.0402 (13) | |
C37 | 0.6785 (3) | 0.2536 (6) | 0.4714 (2) | 0.0560 (16) | |
H37A | 0.6731 | 0.1910 | 0.4467 | 0.067* | |
C38 | 0.7334 (3) | 0.2426 (6) | 0.5125 (2) | 0.0635 (17) | |
H38A | 0.7663 | 0.1730 | 0.5148 | 0.076* | |
C39 | 0.7419 (3) | 0.3308 (6) | 0.5509 (2) | 0.0626 (18) | |
H39A | 0.7792 | 0.3182 | 0.5789 | 0.075* | |
C40 | 0.6954 (3) | 0.4379 (6) | 0.5482 (2) | 0.0607 (17) | |
H40A | 0.7010 | 0.4982 | 0.5738 | 0.073* | |
C41 | 0.6397 (3) | 0.4520 (5) | 0.5056 (2) | 0.0483 (15) | |
C42 | 0.5479 (3) | 0.5207 (5) | 0.4455 (2) | 0.0465 (14) | |
C43 | 0.4962 (3) | 0.6238 (6) | 0.4224 (2) | 0.0506 (15) | |
C44 | 0.4048 (4) | 0.6789 (6) | 0.3526 (3) | 0.089 (2) | |
H44A | 0.3779 | 0.6409 | 0.3224 | 0.134* | |
H44B | 0.3701 | 0.7067 | 0.3725 | 0.134* | |
H44C | 0.4329 | 0.7522 | 0.3449 | 0.134* | |
C45 | 0.5442 (3) | 0.1959 (5) | 0.3796 (2) | 0.0434 (14) | |
C46 | 0.5886 (3) | 0.1132 (5) | 0.3559 (2) | 0.0469 (15) | |
C47 | 0.6385 (3) | 0.1274 (6) | 0.3240 (2) | 0.0561 (17) | |
H47A | 0.6513 | 0.2098 | 0.3147 | 0.067* | |
C48 | 0.6686 (4) | 0.0199 (7) | 0.3062 (3) | 0.073 (2) | |
H48A | 0.7019 | 0.0302 | 0.2849 | 0.088* | |
C49 | 0.6505 (4) | −0.1041 (6) | 0.3196 (2) | 0.0636 (19) | |
H49A | 0.6721 | −0.1752 | 0.3071 | 0.076* | |
C50 | 0.6018 (3) | −0.1247 (6) | 0.3504 (2) | 0.0596 (17) | |
H50A | 0.5888 | −0.2081 | 0.3584 | 0.072* | |
C51 | 0.5727 (3) | −0.0167 (5) | 0.3692 (2) | 0.0455 (15) | |
C52 | 0.5040 (3) | 0.1183 (5) | 0.4053 (2) | 0.0475 (15) | |
C53 | 0.4451 (3) | 0.1516 (6) | 0.4333 (2) | 0.0460 (15) | |
C54 | 0.3624 (4) | 0.0783 (6) | 0.4808 (3) | 0.084 (2) | |
H54A | 0.3478 | −0.0005 | 0.4949 | 0.126* | |
H54B | 0.3804 | 0.1393 | 0.5068 | 0.126* | |
H54C | 0.3202 | 0.1144 | 0.4586 | 0.126* | |
C55 | 1.1147 (7) | 0.2243 (9) | 0.1965 (4) | 0.226 (8) | |
H55A | 1.1595 | 0.1774 | 0.1930 | 0.271* | |
H55B | 1.1060 | 0.2029 | 0.2292 | 0.271* | |
C56 | 1.1354 (5) | 0.3581 (9) | 0.1991 (4) | 0.151 (4) | |
H56A | 1.1776 | 0.3708 | 0.2256 | 0.227* | |
H56B | 1.1484 | 0.3838 | 0.1683 | 0.227* | |
H56C | 1.0942 | 0.4096 | 0.2049 | 0.227* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.070 (4) | 0.031 (3) | 0.059 (3) | −0.009 (3) | 0.007 (3) | −0.009 (2) |
C1 | 0.042 (3) | 0.035 (3) | 0.045 (3) | 0.004 (3) | 0.007 (3) | −0.010 (3) |
N1 | 0.098 (5) | 0.071 (4) | 0.058 (4) | −0.008 (4) | 0.018 (4) | −0.002 (3) |
O1 | 0.152 (6) | 0.222 (8) | 0.063 (4) | −0.065 (5) | 0.013 (4) | 0.040 (5) |
C2 | 0.048 (4) | 0.030 (3) | 0.041 (3) | 0.000 (3) | 0.004 (3) | −0.004 (3) |
O2 | 0.097 (4) | 0.074 (3) | 0.091 (4) | −0.020 (3) | 0.041 (3) | −0.009 (3) |
O3 | 0.056 (3) | 0.062 (3) | 0.093 (4) | −0.017 (2) | 0.024 (3) | 0.003 (3) |
N3 | 0.071 (3) | 0.037 (3) | 0.036 (3) | 0.001 (3) | 0.005 (2) | −0.002 (2) |
C3 | 0.054 (4) | 0.068 (4) | 0.047 (4) | −0.012 (3) | 0.001 (3) | 0.007 (3) |
N4 | 0.079 (5) | 0.134 (6) | 0.064 (4) | 0.005 (4) | 0.016 (4) | 0.029 (5) |
O4 | 0.063 (3) | 0.051 (3) | 0.062 (3) | −0.002 (2) | 0.023 (2) | −0.011 (2) |
C4 | 0.081 (5) | 0.073 (4) | 0.033 (4) | −0.014 (4) | −0.001 (3) | 0.010 (3) |
O5 | 0.107 (4) | 0.050 (3) | 0.054 (3) | 0.028 (3) | −0.011 (3) | −0.005 (2) |
C5 | 0.070 (5) | 0.046 (4) | 0.059 (5) | −0.006 (3) | 0.033 (4) | −0.002 (3) |
N5 | 0.061 (3) | 0.028 (3) | 0.057 (3) | −0.006 (2) | 0.014 (3) | −0.011 (2) |
O6 | 0.093 (3) | 0.033 (2) | 0.060 (3) | 0.013 (2) | 0.004 (2) | −0.008 (2) |
C6 | 0.062 (4) | 0.053 (4) | 0.047 (4) | −0.018 (3) | 0.005 (3) | −0.012 (3) |
N6 | 0.062 (3) | 0.021 (2) | 0.072 (4) | 0.001 (2) | 0.009 (3) | 0.000 (2) |
O7 | 0.154 (6) | 0.131 (5) | 0.099 (5) | −0.043 (5) | 0.055 (4) | 0.009 (4) |
C7 | 0.059 (4) | 0.064 (4) | 0.046 (4) | −0.008 (3) | 0.005 (3) | −0.002 (3) |
O8 | 0.111 (5) | 0.280 (9) | 0.076 (4) | −0.012 (5) | 0.002 (4) | 0.062 (5) |
C8 | 0.047 (4) | 0.032 (3) | 0.041 (3) | −0.001 (3) | 0.008 (3) | −0.001 (3) |
C9 | 0.057 (4) | 0.034 (3) | 0.032 (3) | −0.001 (3) | 0.008 (3) | −0.002 (3) |
O9 | 0.067 (3) | 0.043 (2) | 0.089 (4) | 0.019 (2) | −0.002 (3) | 0.009 (2) |
O10 | 0.094 (4) | 0.028 (2) | 0.100 (4) | 0.004 (2) | 0.020 (3) | −0.005 (2) |
C10 | 0.056 (4) | 0.044 (4) | 0.061 (4) | −0.003 (3) | 0.014 (3) | −0.011 (3) |
C11 | 0.057 (4) | 0.062 (4) | 0.070 (5) | 0.022 (4) | 0.015 (4) | 0.008 (4) |
O11 | 0.075 (3) | 0.049 (3) | 0.109 (4) | −0.011 (2) | 0.040 (3) | 0.017 (3) |
C12 | 0.079 (5) | 0.054 (4) | 0.084 (5) | 0.019 (4) | 0.025 (4) | −0.005 (4) |
O12 | 0.069 (3) | 0.040 (2) | 0.072 (3) | 0.004 (2) | 0.025 (2) | −0.005 (2) |
C13 | 0.074 (5) | 0.036 (3) | 0.071 (5) | 0.009 (3) | 0.017 (4) | −0.005 (3) |
O13 | 0.187 (6) | 0.069 (4) | 0.136 (5) | −0.052 (4) | −0.079 (5) | 0.024 (4) |
C14 | 0.053 (4) | 0.046 (4) | 0.045 (4) | 0.004 (3) | 0.013 (3) | −0.005 (3) |
C15 | 0.051 (4) | 0.039 (3) | 0.039 (3) | −0.009 (3) | 0.006 (3) | −0.004 (3) |
C16 | 0.041 (4) | 0.053 (4) | 0.042 (3) | −0.012 (3) | 0.003 (3) | −0.007 (3) |
C17 | 0.054 (5) | 0.104 (6) | 0.138 (7) | −0.024 (4) | 0.037 (5) | −0.002 (5) |
C18 | 0.039 (3) | 0.039 (3) | 0.036 (3) | −0.009 (3) | 0.006 (3) | 0.000 (3) |
C19 | 0.049 (4) | 0.038 (3) | 0.038 (3) | −0.004 (3) | 0.009 (3) | −0.005 (3) |
C20 | 0.063 (4) | 0.046 (4) | 0.055 (4) | 0.006 (3) | 0.012 (3) | 0.001 (3) |
C21 | 0.071 (5) | 0.058 (4) | 0.054 (4) | 0.019 (3) | 0.009 (4) | 0.004 (4) |
C22 | 0.081 (5) | 0.062 (4) | 0.044 (4) | 0.020 (4) | −0.010 (3) | 0.009 (3) |
C23 | 0.069 (4) | 0.062 (4) | 0.057 (4) | 0.003 (4) | 0.005 (3) | 0.000 (4) |
C24 | 0.056 (4) | 0.038 (3) | 0.040 (4) | 0.005 (3) | 0.009 (3) | 0.004 (3) |
C25 | 0.056 (4) | 0.029 (3) | 0.047 (4) | −0.003 (3) | 0.014 (3) | −0.002 (3) |
C26 | 0.053 (4) | 0.036 (3) | 0.056 (4) | 0.001 (3) | 0.015 (3) | −0.009 (3) |
C27 | 0.109 (6) | 0.042 (4) | 0.079 (5) | 0.021 (4) | 0.021 (4) | 0.007 (4) |
C28 | 0.039 (3) | 0.033 (3) | 0.057 (4) | −0.003 (3) | 0.005 (3) | −0.006 (3) |
C29 | 0.039 (3) | 0.030 (3) | 0.057 (4) | 0.004 (3) | 0.005 (3) | 0.005 (3) |
C30 | 0.053 (4) | 0.082 (5) | 0.067 (5) | −0.018 (4) | −0.007 (4) | 0.007 (4) |
C31 | 0.066 (5) | 0.128 (7) | 0.043 (4) | −0.006 (5) | −0.002 (4) | 0.015 (4) |
C32 | 0.066 (5) | 0.057 (4) | 0.051 (4) | 0.009 (4) | 0.013 (4) | 0.017 (3) |
C33 | 0.059 (4) | 0.047 (4) | 0.064 (5) | −0.005 (3) | 0.009 (4) | −0.005 (3) |
C34 | 0.058 (4) | 0.052 (4) | 0.053 (4) | −0.004 (3) | 0.005 (3) | −0.004 (3) |
C35 | 0.039 (3) | 0.028 (3) | 0.061 (4) | −0.002 (3) | 0.012 (3) | 0.001 (3) |
C36 | 0.044 (3) | 0.026 (3) | 0.050 (4) | −0.004 (3) | 0.007 (3) | 0.005 (3) |
C37 | 0.051 (4) | 0.055 (4) | 0.059 (4) | −0.003 (3) | 0.005 (3) | 0.002 (3) |
C38 | 0.070 (5) | 0.056 (4) | 0.059 (4) | 0.006 (4) | −0.001 (4) | 0.001 (4) |
C39 | 0.065 (4) | 0.057 (4) | 0.062 (5) | −0.003 (4) | 0.002 (3) | 0.013 (4) |
C40 | 0.075 (5) | 0.055 (4) | 0.049 (4) | −0.022 (4) | 0.005 (3) | 0.001 (3) |
C41 | 0.057 (4) | 0.037 (3) | 0.052 (4) | −0.009 (3) | 0.014 (3) | 0.002 (3) |
C42 | 0.040 (3) | 0.041 (3) | 0.057 (4) | −0.004 (3) | 0.006 (3) | 0.006 (3) |
C43 | 0.045 (4) | 0.042 (4) | 0.068 (5) | −0.004 (3) | 0.016 (3) | 0.006 (3) |
C44 | 0.071 (5) | 0.060 (4) | 0.129 (7) | 0.013 (4) | 0.000 (5) | 0.013 (5) |
C45 | 0.038 (3) | 0.029 (3) | 0.058 (4) | −0.009 (3) | −0.002 (3) | −0.002 (3) |
C46 | 0.047 (4) | 0.031 (3) | 0.061 (4) | 0.001 (3) | 0.007 (3) | −0.011 (3) |
C47 | 0.056 (4) | 0.041 (4) | 0.074 (5) | 0.006 (3) | 0.020 (4) | −0.005 (3) |
C48 | 0.068 (5) | 0.073 (5) | 0.085 (5) | 0.009 (4) | 0.031 (4) | −0.009 (4) |
C49 | 0.074 (5) | 0.034 (4) | 0.080 (5) | 0.013 (3) | 0.007 (4) | −0.010 (3) |
C50 | 0.057 (4) | 0.040 (4) | 0.084 (5) | 0.002 (3) | 0.019 (4) | −0.005 (3) |
C51 | 0.040 (3) | 0.034 (3) | 0.062 (4) | 0.005 (3) | 0.011 (3) | −0.013 (3) |
C52 | 0.050 (4) | 0.032 (3) | 0.058 (4) | −0.006 (3) | 0.004 (3) | −0.003 (3) |
C53 | 0.042 (4) | 0.045 (4) | 0.049 (4) | −0.006 (3) | 0.005 (3) | −0.011 (3) |
C54 | 0.084 (5) | 0.072 (5) | 0.113 (6) | −0.009 (4) | 0.060 (5) | 0.010 (4) |
C55 | 0.255 (14) | 0.116 (9) | 0.228 (14) | −0.099 (9) | −0.142 (11) | 0.105 (9) |
C56 | 0.115 (8) | 0.165 (10) | 0.157 (10) | −0.038 (7) | −0.013 (7) | −0.020 (8) |
N2—C15 | 1.362 (6) | C19—C24 | 1.410 (7) |
N2—C14 | 1.371 (6) | C20—C21 | 1.364 (7) |
N2—H2A | 0.8600 | C20—H20A | 0.9300 |
C1—C8 | 1.516 (7) | C21—C22 | 1.391 (8) |
C1—C2 | 1.515 (7) | C21—H21A | 0.9300 |
C1—C18 | 1.522 (7) | C22—C23 | 1.380 (8) |
C1—H1A | 0.9800 | C22—H22A | 0.9300 |
N1—O1 | 1.189 (7) | C23—C24 | 1.402 (7) |
N1—O2 | 1.205 (6) | C23—H23A | 0.9300 |
N1—C5 | 1.479 (8) | C25—C26 | 1.461 (7) |
C2—C3 | 1.366 (7) | C27—H27A | 0.9600 |
C2—C7 | 1.380 (7) | C27—H27B | 0.9600 |
O3—C16 | 1.349 (6) | C27—H27C | 0.9600 |
O3—C17 | 1.436 (6) | C28—C29 | 1.509 (7) |
N3—C24 | 1.349 (6) | C28—C35 | 1.517 (7) |
N3—C25 | 1.365 (6) | C28—C45 | 1.531 (7) |
N3—H3A | 0.8600 | C28—H28A | 0.9800 |
C3—C4 | 1.372 (7) | C29—C30 | 1.364 (7) |
C3—H3B | 0.9300 | C29—C34 | 1.383 (7) |
N4—O8 | 1.217 (8) | C30—C31 | 1.376 (8) |
N4—O7 | 1.217 (7) | C30—H30A | 0.9300 |
N4—C32 | 1.449 (8) | C31—C32 | 1.368 (8) |
O4—C16 | 1.211 (6) | C31—H31A | 0.9300 |
C4—C5 | 1.375 (7) | C32—C33 | 1.353 (8) |
C4—H4A | 0.9300 | C33—C34 | 1.368 (7) |
O5—C26 | 1.202 (6) | C33—H33A | 0.9300 |
C5—C6 | 1.352 (8) | C34—H34A | 0.9300 |
N5—C41 | 1.360 (6) | C35—C42 | 1.367 (7) |
N5—C42 | 1.375 (6) | C35—C36 | 1.429 (7) |
N5—H5A | 0.8600 | C36—C37 | 1.406 (7) |
O6—C26 | 1.330 (6) | C36—C41 | 1.409 (7) |
O6—C27 | 1.442 (6) | C37—C38 | 1.359 (7) |
C6—C7 | 1.392 (7) | C37—H37A | 0.9300 |
C6—H6A | 0.9300 | C38—C39 | 1.381 (8) |
N6—C51 | 1.363 (6) | C38—H38A | 0.9300 |
N6—C52 | 1.384 (6) | C39—C40 | 1.385 (8) |
N6—H6B | 0.8600 | C39—H39A | 0.9300 |
C7—H7A | 0.9300 | C40—C41 | 1.401 (7) |
C8—C15 | 1.358 (7) | C40—H40A | 0.9300 |
C8—C9 | 1.440 (7) | C42—C43 | 1.478 (7) |
C9—C10 | 1.399 (7) | C44—H44A | 0.9600 |
C9—C14 | 1.402 (7) | C44—H44B | 0.9600 |
O9—C43 | 1.333 (7) | C44—H44C | 0.9600 |
O9—C44 | 1.437 (6) | C45—C52 | 1.372 (7) |
O10—C43 | 1.198 (6) | C45—C46 | 1.422 (7) |
C10—C11 | 1.367 (7) | C46—C47 | 1.392 (7) |
C10—H10A | 0.9300 | C46—C51 | 1.432 (7) |
C11—C12 | 1.395 (8) | C47—C48 | 1.369 (8) |
C11—H11A | 0.9300 | C47—H47A | 0.9300 |
O11—C53 | 1.307 (6) | C48—C49 | 1.388 (8) |
O11—C54 | 1.438 (6) | C48—H48A | 0.9300 |
C12—C13 | 1.346 (8) | C49—C50 | 1.361 (8) |
C12—H12A | 0.9300 | C49—H49A | 0.9300 |
O12—C53 | 1.214 (6) | C50—C51 | 1.378 (7) |
C13—C14 | 1.390 (7) | C50—H50A | 0.9300 |
C13—H13A | 0.9300 | C52—C53 | 1.482 (7) |
O13—C55 | 1.259 (9) | C54—H54A | 0.9600 |
O13—H13B | 0.8200 | C54—H54B | 0.9600 |
C15—C16 | 1.447 (7) | C54—H54C | 0.9600 |
C17—H17A | 0.9600 | C55—C56 | 1.427 (8) |
C17—H17B | 0.9600 | C55—H55A | 0.9700 |
C17—H17C | 0.9600 | C55—H55B | 0.9700 |
C18—C25 | 1.376 (7) | C56—H56A | 0.9600 |
C18—C19 | 1.426 (7) | C56—H56B | 0.9600 |
C19—C20 | 1.394 (7) | C56—H56C | 0.9600 |
C15—N2—C14 | 109.1 (5) | O6—C27—H27B | 109.5 |
C15—N2—H2A | 125.5 | H27A—C27—H27B | 109.5 |
C14—N2—H2A | 125.5 | O6—C27—H27C | 109.5 |
C8—C1—C2 | 112.0 (4) | H27A—C27—H27C | 109.5 |
C8—C1—C18 | 113.5 (4) | H27B—C27—H27C | 109.5 |
C2—C1—C18 | 114.6 (4) | C29—C28—C35 | 112.2 (4) |
C8—C1—H1A | 105.2 | C29—C28—C45 | 113.6 (5) |
C2—C1—H1A | 105.2 | C35—C28—C45 | 112.7 (5) |
C18—C1—H1A | 105.2 | C29—C28—H28A | 105.9 |
O1—N1—O2 | 123.5 (7) | C35—C28—H28A | 105.9 |
O1—N1—C5 | 118.3 (7) | C45—C28—H28A | 105.9 |
O2—N1—C5 | 118.2 (6) | C30—C29—C34 | 116.7 (6) |
C3—C2—C7 | 117.4 (5) | C30—C29—C28 | 121.2 (5) |
C3—C2—C1 | 118.6 (5) | C34—C29—C28 | 122.1 (5) |
C7—C2—C1 | 124.0 (5) | C29—C30—C31 | 122.7 (6) |
C16—O3—C17 | 116.3 (5) | C29—C30—H30A | 118.6 |
C24—N3—C25 | 108.7 (5) | C31—C30—H30A | 118.6 |
C24—N3—H3A | 125.6 | C32—C31—C30 | 117.9 (6) |
C25—N3—H3A | 125.6 | C32—C31—H31A | 121.0 |
C2—C3—C4 | 122.7 (6) | C30—C31—H31A | 121.0 |
C2—C3—H3B | 118.6 | C33—C32—C31 | 121.7 (6) |
C4—C3—H3B | 118.6 | C33—C32—N4 | 119.5 (7) |
O8—N4—O7 | 122.5 (7) | C31—C32—N4 | 118.8 (6) |
O8—N4—C32 | 119.0 (7) | C32—C33—C34 | 118.9 (6) |
O7—N4—C32 | 118.1 (7) | C32—C33—H33A | 120.6 |
C3—C4—C5 | 117.6 (6) | C34—C33—H33A | 120.6 |
C3—C4—H4A | 121.2 | C33—C34—C29 | 122.1 (6) |
C5—C4—H4A | 121.2 | C33—C34—H34A | 118.9 |
C6—C5—C4 | 122.7 (6) | C29—C34—H34A | 118.9 |
C6—C5—N1 | 118.3 (6) | C42—C35—C36 | 105.5 (5) |
C4—C5—N1 | 119.1 (6) | C42—C35—C28 | 125.2 (5) |
C41—N5—C42 | 108.9 (5) | C36—C35—C28 | 129.2 (5) |
C41—N5—H5A | 125.5 | C37—C36—C41 | 118.1 (5) |
C42—N5—H5A | 125.5 | C37—C36—C35 | 134.0 (5) |
C26—O6—C27 | 115.2 (5) | C41—C36—C35 | 107.8 (5) |
C5—C6—C7 | 117.8 (6) | C38—C37—C36 | 119.3 (6) |
C5—C6—H6A | 121.1 | C38—C37—H37A | 120.3 |
C7—C6—H6A | 121.1 | C36—C37—H37A | 120.3 |
C51—N6—C52 | 108.8 (5) | C37—C38—C39 | 122.4 (6) |
C51—N6—H6B | 125.6 | C37—C38—H38A | 118.8 |
C52—N6—H6B | 125.6 | C39—C38—H38A | 118.8 |
C2—C7—C6 | 121.7 (6) | C40—C39—C38 | 120.6 (6) |
C2—C7—H7A | 119.1 | C40—C39—H39A | 119.7 |
C6—C7—H7A | 119.1 | C38—C39—H39A | 119.7 |
C15—C8—C9 | 106.3 (5) | C39—C40—C41 | 117.6 (6) |
C15—C8—C1 | 125.8 (5) | C39—C40—H40A | 121.2 |
C9—C8—C1 | 127.9 (5) | C41—C40—H40A | 121.2 |
C10—C9—C14 | 117.4 (5) | N5—C41—C40 | 130.6 (6) |
C10—C9—C8 | 135.7 (5) | N5—C41—C36 | 107.3 (5) |
C14—C9—C8 | 106.7 (5) | C40—C41—C36 | 122.0 (6) |
C43—O9—C44 | 116.1 (5) | C35—C42—N5 | 110.5 (5) |
C11—C10—C9 | 120.0 (6) | C35—C42—C43 | 133.6 (6) |
C11—C10—H10A | 120.0 | N5—C42—C43 | 115.6 (5) |
C9—C10—H10A | 120.0 | O10—C43—O9 | 123.8 (6) |
C10—C11—C12 | 120.6 (6) | O10—C43—C42 | 124.9 (6) |
C10—C11—H11A | 119.7 | O9—C43—C42 | 111.2 (5) |
C12—C11—H11A | 119.7 | O9—C44—H44A | 109.5 |
C53—O11—C54 | 114.6 (5) | O9—C44—H44B | 109.5 |
C13—C12—C11 | 121.3 (6) | H44A—C44—H44B | 109.5 |
C13—C12—H12A | 119.3 | O9—C44—H44C | 109.5 |
C11—C12—H12A | 119.3 | H44A—C44—H44C | 109.5 |
C12—C13—C14 | 118.3 (6) | H44B—C44—H44C | 109.5 |
C12—C13—H13A | 120.9 | C52—C45—C46 | 107.4 (5) |
C14—C13—H13A | 120.9 | C52—C45—C28 | 122.6 (5) |
C55—O13—H13B | 109.5 | C46—C45—C28 | 129.9 (5) |
N2—C14—C13 | 130.1 (6) | C47—C46—C45 | 137.0 (5) |
N2—C14—C9 | 107.6 (5) | C47—C46—C51 | 116.8 (5) |
C13—C14—C9 | 122.3 (6) | C45—C46—C51 | 106.2 (5) |
C8—C15—N2 | 110.3 (5) | C48—C47—C46 | 120.0 (6) |
C8—C15—C16 | 127.8 (5) | C48—C47—H47A | 120.0 |
N2—C15—C16 | 121.8 (5) | C46—C47—H47A | 120.0 |
O4—C16—O3 | 122.5 (5) | C47—C48—C49 | 121.1 (6) |
O4—C16—C15 | 126.5 (5) | C47—C48—H48A | 119.5 |
O3—C16—C15 | 111.0 (5) | C49—C48—H48A | 119.5 |
O3—C17—H17A | 109.5 | C50—C49—C48 | 121.9 (6) |
O3—C17—H17B | 109.5 | C50—C49—H49A | 119.1 |
H17A—C17—H17B | 109.5 | C48—C49—H49A | 119.1 |
O3—C17—H17C | 109.5 | C49—C50—C51 | 117.2 (6) |
H17A—C17—H17C | 109.5 | C49—C50—H50A | 121.4 |
H17B—C17—H17C | 109.5 | C51—C50—H50A | 121.4 |
C25—C18—C19 | 106.1 (5) | N6—C51—C50 | 128.8 (5) |
C25—C18—C1 | 124.0 (5) | N6—C51—C46 | 108.0 (5) |
C19—C18—C1 | 129.8 (5) | C50—C51—C46 | 123.1 (5) |
C20—C19—C24 | 117.1 (5) | C45—C52—N6 | 109.6 (5) |
C20—C19—C18 | 136.6 (5) | C45—C52—C53 | 130.5 (5) |
C24—C19—C18 | 106.3 (5) | N6—C52—C53 | 119.7 (5) |
C21—C20—C19 | 120.6 (6) | O12—C53—O11 | 125.5 (5) |
C21—C20—H20A | 119.7 | O12—C53—C52 | 121.8 (5) |
C19—C20—H20A | 119.7 | O11—C53—C52 | 112.8 (5) |
C20—C21—C22 | 121.2 (6) | O11—C54—H54A | 109.5 |
C20—C21—H21A | 119.4 | O11—C54—H54B | 109.5 |
C22—C21—H21A | 119.4 | H54A—C54—H54B | 109.5 |
C23—C22—C21 | 121.2 (6) | O11—C54—H54C | 109.5 |
C23—C22—H22A | 119.4 | H54A—C54—H54C | 109.5 |
C21—C22—H22A | 119.4 | H54B—C54—H54C | 109.5 |
C22—C23—C24 | 116.7 (6) | O13—C55—C56 | 127.6 (9) |
C22—C23—H23A | 121.7 | O13—C55—H55A | 105.4 |
C24—C23—H23A | 121.7 | C56—C55—H55A | 105.4 |
N3—C24—C23 | 128.0 (5) | O13—C55—H55B | 105.4 |
N3—C24—C19 | 108.8 (5) | C56—C55—H55B | 105.4 |
C23—C24—C19 | 123.2 (5) | H55A—C55—H55B | 106.0 |
N3—C25—C18 | 110.1 (5) | C55—C56—H56A | 109.5 |
N3—C25—C26 | 121.6 (5) | C55—C56—H56B | 109.5 |
C18—C25—C26 | 128.3 (5) | H56A—C56—H56B | 109.5 |
O5—C26—O6 | 124.0 (5) | C55—C56—H56C | 109.5 |
O5—C26—C25 | 124.7 (5) | H56A—C56—H56C | 109.5 |
O6—C26—C25 | 111.3 (5) | H56B—C56—H56C | 109.5 |
O6—C27—H27A | 109.5 | ||
C8—C1—C2—C3 | −67.2 (6) | C35—C28—C29—C30 | −154.9 (5) |
C18—C1—C2—C3 | 161.6 (5) | C45—C28—C29—C30 | 75.9 (7) |
C8—C1—C2—C7 | 112.2 (6) | C35—C28—C29—C34 | 25.8 (7) |
C18—C1—C2—C7 | −19.0 (7) | C45—C28—C29—C34 | −103.4 (6) |
C7—C2—C3—C4 | −1.8 (9) | C34—C29—C30—C31 | −0.2 (10) |
C1—C2—C3—C4 | 177.6 (5) | C28—C29—C30—C31 | −179.5 (6) |
C2—C3—C4—C5 | −0.4 (9) | C29—C30—C31—C32 | 0.3 (11) |
C3—C4—C5—C6 | 1.4 (9) | C30—C31—C32—C33 | 0.6 (10) |
C3—C4—C5—N1 | −177.5 (6) | C30—C31—C32—N4 | 177.8 (7) |
O1—N1—C5—C6 | 177.4 (7) | O8—N4—C32—C33 | 164.3 (7) |
O2—N1—C5—C6 | −2.3 (9) | O7—N4—C32—C33 | −9.2 (10) |
O1—N1—C5—C4 | −3.6 (10) | O8—N4—C32—C31 | −12.9 (11) |
O2—N1—C5—C4 | 176.7 (6) | O7—N4—C32—C31 | 173.5 (7) |
C4—C5—C6—C7 | −0.2 (9) | C31—C32—C33—C34 | −1.7 (10) |
N1—C5—C6—C7 | 178.8 (5) | N4—C32—C33—C34 | −178.8 (6) |
C3—C2—C7—C6 | 3.1 (8) | C32—C33—C34—C29 | 1.8 (9) |
C1—C2—C7—C6 | −176.3 (5) | C30—C29—C34—C33 | −0.9 (8) |
C5—C6—C7—C2 | −2.2 (9) | C28—C29—C34—C33 | 178.4 (5) |
C2—C1—C8—C15 | 141.4 (5) | C29—C28—C35—C42 | 77.0 (7) |
C18—C1—C8—C15 | −86.9 (6) | C45—C28—C35—C42 | −153.3 (5) |
C2—C1—C8—C9 | −35.8 (7) | C29—C28—C35—C36 | −98.6 (6) |
C18—C1—C8—C9 | 95.9 (6) | C45—C28—C35—C36 | 31.1 (8) |
C15—C8—C9—C10 | 176.7 (6) | C42—C35—C36—C37 | −176.1 (6) |
C1—C8—C9—C10 | −5.7 (10) | C28—C35—C36—C37 | 0.2 (10) |
C15—C8—C9—C14 | 1.5 (6) | C42—C35—C36—C41 | 2.2 (6) |
C1—C8—C9—C14 | 179.2 (5) | C28—C35—C36—C41 | 178.5 (5) |
C14—C9—C10—C11 | −1.8 (8) | C41—C36—C37—C38 | −0.9 (8) |
C8—C9—C10—C11 | −176.5 (6) | C35—C36—C37—C38 | 177.3 (6) |
C9—C10—C11—C12 | 0.2 (9) | C36—C37—C38—C39 | 2.2 (9) |
C10—C11—C12—C13 | 0.6 (10) | C37—C38—C39—C40 | −2.1 (10) |
C11—C12—C13—C14 | 0.4 (10) | C38—C39—C40—C41 | 0.5 (9) |
C15—N2—C14—C13 | 179.8 (6) | C42—N5—C41—C40 | 178.0 (6) |
C15—N2—C14—C9 | −0.8 (6) | C42—N5—C41—C36 | 1.3 (6) |
C12—C13—C14—N2 | 177.2 (6) | C39—C40—C41—N5 | −175.5 (6) |
C12—C13—C14—C9 | −2.1 (9) | C39—C40—C41—C36 | 0.7 (8) |
C10—C9—C14—N2 | −176.6 (5) | C37—C36—C41—N5 | 176.5 (5) |
C8—C9—C14—N2 | −0.5 (6) | C35—C36—C41—N5 | −2.1 (6) |
C10—C9—C14—C13 | 2.8 (8) | C37—C36—C41—C40 | −0.6 (8) |
C8—C9—C14—C13 | 179.0 (5) | C35—C36—C41—C40 | −179.2 (5) |
C9—C8—C15—N2 | −2.1 (6) | C36—C35—C42—N5 | −1.4 (6) |
C1—C8—C15—N2 | −179.8 (5) | C28—C35—C42—N5 | −177.9 (5) |
C9—C8—C15—C16 | −178.3 (5) | C36—C35—C42—C43 | 170.9 (6) |
C1—C8—C15—C16 | 4.0 (9) | C28—C35—C42—C43 | −5.5 (9) |
C14—N2—C15—C8 | 1.8 (6) | C41—N5—C42—C35 | 0.1 (6) |
C14—N2—C15—C16 | 178.3 (5) | C41—N5—C42—C43 | −173.8 (4) |
C17—O3—C16—O4 | −1.4 (8) | C44—O9—C43—O10 | 1.7 (9) |
C17—O3—C16—C15 | 178.1 (5) | C44—O9—C43—C42 | −177.4 (5) |
C8—C15—C16—O4 | −13.5 (9) | C35—C42—C43—O10 | −167.3 (6) |
N2—C15—C16—O4 | 170.7 (6) | N5—C42—C43—O10 | 4.7 (8) |
C8—C15—C16—O3 | 167.0 (5) | C35—C42—C43—O9 | 11.8 (9) |
N2—C15—C16—O3 | −8.8 (7) | N5—C42—C43—O9 | −176.2 (5) |
C8—C1—C18—C25 | 151.5 (5) | C29—C28—C45—C52 | −162.7 (5) |
C2—C1—C18—C25 | −78.0 (6) | C35—C28—C45—C52 | 68.3 (7) |
C8—C1—C18—C19 | −28.3 (8) | C29—C28—C45—C46 | 17.1 (8) |
C2—C1—C18—C19 | 102.1 (6) | C35—C28—C45—C46 | −111.9 (7) |
C25—C18—C19—C20 | −178.6 (6) | C52—C45—C46—C47 | 177.4 (7) |
C1—C18—C19—C20 | 1.3 (10) | C28—C45—C46—C47 | −2.4 (11) |
C25—C18—C19—C24 | −1.4 (6) | C52—C45—C46—C51 | −0.4 (6) |
C1—C18—C19—C24 | 178.5 (5) | C28—C45—C46—C51 | 179.8 (5) |
C24—C19—C20—C21 | 1.3 (8) | C45—C46—C47—C48 | −176.4 (7) |
C18—C19—C20—C21 | 178.2 (6) | C51—C46—C47—C48 | 1.2 (9) |
C19—C20—C21—C22 | 0.6 (9) | C46—C47—C48—C49 | −0.1 (10) |
C20—C21—C22—C23 | −0.5 (10) | C47—C48—C49—C50 | 0.4 (11) |
C21—C22—C23—C24 | −1.3 (9) | C48—C49—C50—C51 | −1.9 (10) |
C25—N3—C24—C23 | −178.0 (6) | C52—N6—C51—C50 | −174.8 (6) |
C25—N3—C24—C19 | −0.1 (6) | C52—N6—C51—C46 | 0.4 (6) |
C22—C23—C24—N3 | −179.1 (6) | C49—C50—C51—N6 | 177.6 (6) |
C22—C23—C24—C19 | 3.3 (9) | C49—C50—C51—C46 | 3.1 (9) |
C20—C19—C24—N3 | 178.7 (5) | C47—C46—C51—N6 | −178.3 (5) |
C18—C19—C24—N3 | 1.0 (6) | C45—C46—C51—N6 | 0.0 (6) |
C20—C19—C24—C23 | −3.3 (8) | C47—C46—C51—C50 | −2.8 (9) |
C18—C19—C24—C23 | 179.0 (5) | C45—C46—C51—C50 | 175.5 (5) |
C24—N3—C25—C18 | −0.8 (6) | C46—C45—C52—N6 | 0.6 (6) |
C24—N3—C25—C26 | 179.4 (5) | C28—C45—C52—N6 | −179.6 (5) |
C19—C18—C25—N3 | 1.4 (6) | C46—C45—C52—C53 | −174.8 (5) |
C1—C18—C25—N3 | −178.5 (4) | C28—C45—C52—C53 | 5.0 (10) |
C19—C18—C25—C26 | −178.9 (5) | C51—N6—C52—C45 | −0.6 (6) |
C1—C18—C25—C26 | 1.2 (9) | C51—N6—C52—C53 | 175.4 (5) |
C27—O6—C26—O5 | −0.1 (8) | C54—O11—C53—O12 | −0.2 (9) |
C27—O6—C26—C25 | −179.1 (5) | C54—O11—C53—C52 | −178.7 (5) |
N3—C25—C26—O5 | −176.8 (6) | C45—C52—C53—O12 | 3.1 (10) |
C18—C25—C26—O5 | 3.5 (10) | N6—C52—C53—O12 | −171.9 (5) |
N3—C25—C26—O6 | 2.2 (7) | C45—C52—C53—O11 | −178.3 (6) |
C18—C25—C26—O6 | −177.5 (5) | N6—C52—C53—O11 | 6.7 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O13i | 0.86 | 2.00 | 2.814 (7) | 157 |
N3—H3A···O4ii | 0.86 | 2.05 | 2.892 (6) | 166 |
N5—H5A···O12iii | 0.86 | 2.01 | 2.848 (6) | 163 |
N6—H6B···O10iv | 0.86 | 2.16 | 2.984 (6) | 160 |
O13—H13B···O5 | 0.82 | 1.91 | 2.733 (7) | 177 |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
Funding information
Funding for this research was provided by: Natural Science Foundation of Jiangsu Province (grant No. BK20181486); Natural Science Foundation of the Jiangsu Higher Education Institutions (grant No. 17KJB320001); Qing Lan Project of Jiangsu Province; Training Program of Students Innovation and Entrepreneurship in Jiangsu Province (grant No. 202012920001Y).
References
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Jiang, H., Li, Y.-L., Zhou, J., Sun, H.-S., Zhang, Q.-Y., Shi, X.-H., Zhang, Z.-Y. & Ling, T. (2020). IUCrData, 5, x200912. Google Scholar
Ni, Y.-C. (2008). Curr. Med. Imaging Rev. 4, 96–112. Web of Science CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, H.-S., Li, Y.-L., Jiang, H., Chen, Y.-L. & Hu, Y.-D. (2017). Acta Cryst. E73, 1956–1958. CrossRef IUCr Journals Google Scholar
Sun, H.-S., Li, Y.-L., Jiang, H., Xu, N. & Xu, H. (2014). Acta Cryst. E70, 370–372. CSD CrossRef IUCr Journals Google Scholar
Sun, H.-S., Li, Y.-L., Xu, N., Xu, H. & Zhang, J.-D. (2012). Acta Cryst. E68, o2764. CSD CrossRef IUCr Journals Google Scholar
Sundberg, R. J. (1996). The Chemistry of Indoles, p. 113 New York: Academic Press. Google Scholar
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