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H-indol-3-yl)ethanaminium acetate hemihydrate
and Hirshfeld surface analysis of 2-(1aPG and Research Department of Chemistry, Seethalakshmi Ramaswamy College, Tiruchirappalli-2, Tamil Nadu, India, and bDepartment of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu, India
*Correspondence e-mail: manavaibala@gmail.com
The title molecular salt, C10H13N2+·C2H3O2−·0.5H2O, crystallized with four 2-(1H-indol-3-yl)ethanaminium cations (A, B, C and D) and four acetate anions in the together with two water molecules of crystallization. Each cation is linked to an anion by a C—H⋯π interaction. The alkylaminium side chains have folded conformations, with N—C—C—C torsion angles of −58.5 (3), 59.5 (3), −64.6 (3) and −56.0 (3)° for cations A, B, C and D, respectively. In the crystal, the cations and anions are liked by N—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked by the water molecules via Owater—H⋯O and N—H⋯Owater hydrogen bonds, forming layers lying parallel to the bc plane. The overall intermolecular interactions were investigated using Hirshfeld surfaces analysis.
Keywords: crystal structure; 2-(1H-indol-3-yl)ethanaminium; acetate; trypamine; hydrogen bonding; Hirshfeld surface analysis.
CCDC reference: 1579740
1. Chemical context
2-(1H-Indol-3-yl)ethanamine (tryptamine) is an alkaloid found in plants and fungi and is a possible intermediate in the biosynthetic pathway to the plant hormone indole-3-acetic acid (Takahashi, 1986). It is also found in trace amounts in the mammalian brain, possibly acting as a neuromodulator or neurotransmitter (Jones, 1982). As a relatively strong base (pKa = 10.2), it readily forms salts with a number of organic acids. There are seven known families of serotonin receptors which are tryptamine derivatives, and all of them are neurotransmitters. Hallucinogens all have a high affinity for certain serotonin receptor subtypes and the relative hallucinogenic potencies of various drugs can be gauged by their affinities for these receptors (Glennon et al., 1984; Nichols & Sanders-Bush, 2001; Johnson et al., 1987; Krebs-Thomson et al., 1998). The structures of many hallucinogens are similar to serotonin and have a tryptamine core. Indole analogues, especially of tryptamine derivatives, have been found to be polyamine site antagonists at the N-methyldaspartate receptor (Worthen et al., 2001). Indole and its derivatives are that are present in most plants (such as unripe bananas, broccoli and cloves), almost all flower oils (jasmine and orange blossoms) and coal tar (Waseem & Mark, 2005; Lee et al., 2003). In the pharmaceutical field, it has been discovered that it has antimicrobial and anti-inflammatory properties (Mohammad & Moutaery, 2005). The title compound, namely 2-(1H-indol-3-yl)ethanaminium acetate hemihydrate, was synthesized and its and Hirshfeld surface analysis are reported herein.
2. Structural commentary
The molecular structure of the title salt is shown in Fig. 1. The contains four crystallographically independent 2-(1H-indol-3-yl)ethanaminium cations, four acetate anions and two water molecules. The cations are protonated at the amine N atoms (N2, N4, N6 and N8) and are each linked to an anion by a C—H⋯π interaction (Fig. 1 and Table 1). The alkylaminium side chain in each cation has a folded conformation; the torsion angles are −58.5 (3)° for N2—C1—C2—C3, 59.5 (3)° for N4—C11—C12—C13, −64.6 (3)° for N6—C21—C22—C23 and −56.0 (3)° for N8—C31—C32—C33. These values are similar to those observed in the majority of 2-(1H-indol-3-yl)ethanaminium salts (see Database survey section, §5). In the structure of tryptamine, determined from powder diffraction data (Nowell et al., 2002), the corresponding angle is ca 60.4°.
3. Supramolecular features
In the crystal, the cations and anions are liked by N—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along the b-axis direction (Fig. 2 and Table 1). The chains are linked by the water molecules (O9 and O10) via Owater—H⋯O and N—H⋯Owater hydrogen bonds, forming layers lying parallel to the bc plane (Fig. 2 and Table 1). Within the layers, there are a number of C—H⋯π interactions present (Table 1).
4. Hirshfeld surface analysis
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009) and the associated two-dimensional (2D) fingerprint plots (McKinnon et al., 2007) were performed with CrystalExplorer17 (Turner et al., 2017). The Hirshfeld surface of the title molecular salt mapped over dnorm is given in Fig. 3. The red points, which represent closer contacts and negative dnorm values on the surface, correspond to the N—H⋯O, O—H⋯O and C—H⋯O interactions. The 2D fingerprint plots are given in Fig. 4. They reveal that the principal intermolecular interactions are H⋯H (64.2%), C⋯H/H⋯C (18.8%), O⋯H/H⋯O (15.5%) and N⋯H/H⋯N (1.5%), as shown in Fig. 4.
5. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.40, update November 2018; Groom et al., 2016) for 2-(1H-indol-3-yl)ethanamines yielded 42 hits for structures that include atomic coordinates. In 14 hits, the alkylaminium side chain has an extended conformation, with the absolute value of the N—C—C—C torsion angle varying from ca 169.69° in the thiophene-2-carboxylate salt (CSD refcode LACPUA; Koshima & Honke, 1999) to ca 179.44° in the (2S,3S)-hydrogen tartrate monohydrate salt (SOCMED; Koleva et al., 2009). In 28 hits, the alkylaminium side chain has a folded conformation as in the title cations. For example, in the diphenylacetate salt (WODVUG; Koshima et al., 1999), the torsion angle is ca 64.38°, or for the chloride salt (TRYPTA11; Parsons et al., 2015), the torsion angle is ca −59.43°. An analysis showed that only three compounds crystallize with Z′ > 1. They are tris(tryptaminium) tris(3,5-dinitrobenzoate) bis(quinoline) dihydrate (AWIDAN; Lynch et al., 2016), with Z′ = 3, the benzoate salt (DAMNAH; Terakita et al., 2004), with Z′ = 2, and (cucurbit[6]uril) bis(tryptamine) dichloride pentadecahydrate (DASSOH; Danylyuk & Fedin, 2012), also with Z′ = 2. In DAMNAH, the alkylaminium side chain has a folded conformation, while in the other two compounds the side chain is extended.
6. Synthesis and crystallization
The title compound was synthesized by the reaction of a 1:1 stoichiometric mixture of tryptamine (0.160 mg, Aldrich) and acetic acid (0.060 mg, Merck) in a hot methanolic solution (20 ml) with 10 ml of water. After warming for a few minutes over a water bath, the solution was cooled and kept at room temperature. Within a few days, colourless needle-like crystals, suitable for the X-ray analysis, were obtained (yield 65%).
7. Refinement
Crystal data, data collection and structure . The water O-bound H atoms were located in a difference Fourier map and freely refined. The NH and NH3 hydrogens were originally located in a difference Fourier map but for together with the C-bound H atoms, they were positioned geometrically and refined using a riding model, with N—H = 0.86–0.89 Å and C—H = 0.93–0.97 Å, and with Uiso(H) = 1.5Ueq(C,N) for methyl and aminium H atoms, and 1.2Ueq(C,N) otherwise. The structure was refined as a two-component twin with (02); BASF = 0.074 (1).
details are summarized in Table 2
|
Supporting information
CCDC reference: 1579740
https://doi.org/10.1107/S2056989019003347/su5480sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019003347/su5480Isup2.hkl
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT/XPREP (Bruker, 2016); program(s) used to solve structure: SHELXL2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b) and PLATON (Spek, 2009).C10H13N2+·C2H3O2−·0.5H2O | Z = 8 |
Mr = 229.27 | F(000) = 984 |
Triclinic, P1 | Dx = 1.256 Mg m−3 |
a = 10.8328 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 13.2452 (2) Å | Cell parameters from 9851 reflections |
c = 18.1426 (3) Å | θ = 3.6–72.4° |
α = 111.276 (1)° | µ = 0.72 mm−1 |
β = 90.182 (1)° | T = 296 K |
γ = 90.125 (1)° | Needle, yellow |
V = 2425.70 (7) Å3 | 0.10 × 0.10 × 0.05 mm |
Bruker Kappa APEXIII CMOS diffractometer | 6239 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed tube | Rint = 0.069 |
ω and φ scan | θmax = 72.6°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −13→13 |
Tmin = 0.705, Tmax = 0.754 | k = −16→15 |
49248 measured reflections | l = −21→22 |
9420 independent reflections |
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)] = 0.054 | Hydrogen site location: mixed |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.6703P] where P = (Fo2 + 2Fc2)/3 |
9420 reflections | (Δ/σ)max = 0.001 |
620 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.23 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. Refined as a 2-component twin. BASF = 0.074 (1) |
x | y | z | Uiso*/Ueq | ||
N1 | 0.7460 (2) | 0.15380 (15) | 0.30549 (12) | 0.0469 (5) | |
H1N | 0.712448 | 0.108918 | 0.323851 | 0.056* | |
N2 | 0.58562 (19) | 0.36678 (15) | 0.18666 (11) | 0.0417 (5) | |
H2AN | 0.556481 | 0.300879 | 0.159185 | 0.063* | |
H2BN | 0.540279 | 0.416060 | 0.176314 | 0.063* | |
H2CN | 0.582104 | 0.378500 | 0.238110 | 0.063* | |
C1 | 0.7162 (2) | 0.3750 (2) | 0.16382 (15) | 0.0485 (6) | |
H1A | 0.756250 | 0.434967 | 0.204862 | 0.058* | |
H1B | 0.717643 | 0.389992 | 0.115316 | 0.058* | |
C2 | 0.7870 (3) | 0.2718 (2) | 0.15173 (14) | 0.0478 (6) | |
H2A | 0.749936 | 0.213332 | 0.108028 | 0.057* | |
H2B | 0.871094 | 0.281055 | 0.137000 | 0.057* | |
C3 | 0.7902 (2) | 0.23981 (17) | 0.22285 (13) | 0.0370 (5) | |
C4 | 0.7217 (2) | 0.16035 (18) | 0.23366 (14) | 0.0427 (6) | |
H4 | 0.665741 | 0.116330 | 0.196956 | 0.051* | |
C5 | 0.8327 (2) | 0.23072 (18) | 0.34366 (14) | 0.0393 (5) | |
C6 | 0.8882 (3) | 0.2558 (2) | 0.41718 (15) | 0.0511 (7) | |
H6 | 0.867764 | 0.218304 | 0.449981 | 0.061* | |
C7 | 0.9740 (3) | 0.3378 (2) | 0.44000 (17) | 0.0581 (7) | |
H7 | 1.011505 | 0.356765 | 0.489394 | 0.070* | |
C8 | 1.0061 (3) | 0.3931 (2) | 0.39045 (17) | 0.0594 (7) | |
H8 | 1.065694 | 0.447436 | 0.407008 | 0.071* | |
C9 | 0.9515 (2) | 0.3691 (2) | 0.31801 (16) | 0.0500 (6) | |
H9 | 0.973393 | 0.406875 | 0.285679 | 0.060* | |
C10 | 0.8626 (2) | 0.28713 (17) | 0.29309 (14) | 0.0378 (5) | |
N3 | 0.2703 (2) | 0.33098 (16) | 0.69103 (13) | 0.0488 (5) | |
H3N | 0.303553 | 0.371522 | 0.668745 | 0.059* | |
N4 | 0.4274 (2) | 0.13833 (15) | 0.82987 (12) | 0.0486 (5) | |
H4AN | 0.432242 | 0.124335 | 0.778135 | 0.073* | |
H4BN | 0.469902 | 0.088765 | 0.841737 | 0.073* | |
H4CN | 0.458857 | 0.203729 | 0.856258 | 0.073* | |
C11 | 0.2965 (3) | 0.13525 (19) | 0.85230 (15) | 0.0477 (6) | |
H11A | 0.292666 | 0.126283 | 0.902982 | 0.057* | |
H11B | 0.256054 | 0.073273 | 0.813351 | 0.057* | |
C12 | 0.2288 (3) | 0.2371 (2) | 0.85778 (14) | 0.0498 (7) | |
H12A | 0.144212 | 0.231717 | 0.873460 | 0.060* | |
H12B | 0.266920 | 0.298267 | 0.898861 | 0.060* | |
C13 | 0.2276 (2) | 0.25876 (17) | 0.78232 (14) | 0.0398 (6) | |
C14 | 0.2985 (2) | 0.33206 (18) | 0.76495 (15) | 0.0461 (6) | |
H14 | 0.357747 | 0.376541 | 0.798494 | 0.055* | |
C15 | 0.1806 (2) | 0.25507 (18) | 0.65849 (14) | 0.0411 (6) | |
C16 | 0.1220 (3) | 0.2242 (2) | 0.58509 (16) | 0.0568 (7) | |
H16 | 0.143241 | 0.255170 | 0.548317 | 0.068* | |
C17 | 0.0315 (3) | 0.1463 (3) | 0.56926 (18) | 0.0677 (9) | |
H17 | −0.009486 | 0.124404 | 0.520839 | 0.081* | |
C18 | −0.0002 (3) | 0.0995 (2) | 0.62359 (18) | 0.0654 (8) | |
H18 | −0.062175 | 0.047218 | 0.611065 | 0.078* | |
C19 | 0.0581 (3) | 0.1290 (2) | 0.69548 (16) | 0.0522 (7) | |
H19 | 0.036057 | 0.096834 | 0.731362 | 0.063* | |
C20 | 0.1507 (2) | 0.20764 (18) | 0.71446 (13) | 0.0383 (5) | |
N5 | 0.2644 (2) | −0.14717 (15) | 0.19676 (12) | 0.0475 (5) | |
H5N | 0.296545 | −0.210710 | 0.177804 | 0.057* | |
N6 | 0.4361 (2) | 0.18460 (15) | 0.32742 (12) | 0.0474 (5) | |
H6AN | 0.461588 | 0.161044 | 0.365009 | 0.071* | |
H6BN | 0.480121 | 0.242580 | 0.329878 | 0.071* | |
H6CN | 0.446204 | 0.132574 | 0.280243 | 0.071* | |
C21 | 0.3040 (2) | 0.21386 (18) | 0.33925 (15) | 0.0467 (6) | |
H21A | 0.272952 | 0.227723 | 0.293620 | 0.056* | |
H21B | 0.295285 | 0.279873 | 0.385235 | 0.056* | |
C22 | 0.2279 (3) | 0.12453 (19) | 0.35085 (14) | 0.0493 (6) | |
H22A | 0.261412 | 0.109324 | 0.395359 | 0.059* | |
H22B | 0.144073 | 0.150151 | 0.364031 | 0.059* | |
C23 | 0.2246 (2) | 0.02147 (17) | 0.28001 (14) | 0.0396 (5) | |
C24 | 0.2920 (2) | −0.06968 (19) | 0.26856 (15) | 0.0444 (6) | |
H24 | 0.348676 | −0.077948 | 0.304533 | 0.053* | |
C25 | 0.1777 (2) | −0.10725 (18) | 0.16006 (14) | 0.0410 (6) | |
C26 | 0.1195 (3) | −0.1548 (2) | 0.08716 (16) | 0.0547 (7) | |
H26 | 0.138459 | −0.225136 | 0.054130 | 0.066* | |
C27 | 0.0334 (3) | −0.0951 (2) | 0.06532 (18) | 0.0649 (8) | |
H27 | −0.006303 | −0.125367 | 0.016656 | 0.078* | |
C28 | 0.0043 (3) | 0.0098 (3) | 0.11456 (19) | 0.0646 (8) | |
H28 | −0.055184 | 0.048063 | 0.098487 | 0.077* | |
C29 | 0.0618 (3) | 0.0581 (2) | 0.18678 (17) | 0.0531 (7) | |
H29 | 0.041862 | 0.128457 | 0.219234 | 0.064* | |
C30 | 0.1508 (2) | −0.00045 (17) | 0.21039 (14) | 0.0392 (5) | |
N7 | 0.2593 (2) | 0.35813 (15) | 0.18889 (13) | 0.0482 (5) | |
H7N | 0.294125 | 0.296121 | 0.167137 | 0.058* | |
N8 | 0.40770 (19) | 0.69036 (15) | 0.32048 (11) | 0.0430 (5) | |
H8AN | 0.438094 | 0.640145 | 0.337327 | 0.065* | |
H8BN | 0.453345 | 0.750285 | 0.339608 | 0.065* | |
H8CN | 0.409079 | 0.665847 | 0.267862 | 0.065* | |
C31 | 0.2781 (3) | 0.71517 (19) | 0.34835 (15) | 0.0483 (6) | |
H31A | 0.233100 | 0.740203 | 0.311949 | 0.058* | |
H31B | 0.278233 | 0.773101 | 0.399827 | 0.058* | |
C32 | 0.2130 (3) | 0.6172 (2) | 0.35426 (14) | 0.0498 (6) | |
H32A | 0.252725 | 0.597867 | 0.395266 | 0.060* | |
H32B | 0.128300 | 0.636587 | 0.370354 | 0.060* | |
C33 | 0.2123 (2) | 0.51998 (17) | 0.27897 (13) | 0.0375 (5) | |
C34 | 0.2853 (2) | 0.43123 (19) | 0.26256 (15) | 0.0448 (6) | |
H34 | 0.344421 | 0.421696 | 0.296698 | 0.054* | |
C35 | 0.1695 (2) | 0.39916 (18) | 0.15541 (14) | 0.0398 (5) | |
C36 | 0.1129 (3) | 0.3559 (2) | 0.08117 (15) | 0.0531 (7) | |
H36 | 0.136157 | 0.288782 | 0.044803 | 0.064* | |
C37 | 0.0219 (3) | 0.4157 (3) | 0.06369 (17) | 0.0623 (8) | |
H37 | −0.017469 | 0.388519 | 0.014738 | 0.075* | |
C38 | −0.0125 (3) | 0.5161 (2) | 0.11781 (17) | 0.0601 (7) | |
H38 | −0.074693 | 0.554782 | 0.104500 | 0.072* | |
C39 | 0.0436 (2) | 0.5595 (2) | 0.19055 (16) | 0.0495 (6) | |
H39 | 0.019483 | 0.626784 | 0.226234 | 0.059* | |
C40 | 0.1370 (2) | 0.50153 (17) | 0.21034 (13) | 0.0357 (5) | |
O1 | 0.54686 (17) | 0.38518 (13) | 0.34369 (10) | 0.0480 (4) | |
O2 | 0.56930 (18) | 0.56213 (13) | 0.38279 (11) | 0.0557 (5) | |
C41 | 0.5852 (2) | 0.47330 (18) | 0.39205 (13) | 0.0359 (5) | |
C42 | 0.6554 (3) | 0.4733 (2) | 0.46310 (15) | 0.0605 (8) | |
H42A | 0.635115 | 0.537044 | 0.507692 | 0.091* | |
H42B | 0.742370 | 0.472921 | 0.452932 | 0.091* | |
H42C | 0.633916 | 0.410031 | 0.474307 | 0.091* | |
O3 | 0.46376 (17) | 0.12110 (13) | 0.60828 (10) | 0.0495 (4) | |
O4 | 0.40630 (17) | 0.01048 (13) | 0.66873 (9) | 0.0482 (4) | |
C43 | 0.4023 (2) | 0.04290 (16) | 0.61187 (13) | 0.0350 (5) | |
C44 | 0.3194 (3) | −0.0161 (2) | 0.54327 (14) | 0.0501 (6) | |
H44A | 0.341903 | 0.002369 | 0.498563 | 0.075* | |
H44B | 0.235268 | 0.004489 | 0.557315 | 0.075* | |
H44C | 0.327943 | −0.092742 | 0.530034 | 0.075* | |
O5 | 0.46117 (17) | 0.04508 (13) | 0.16035 (10) | 0.0478 (4) | |
O6 | 0.42758 (18) | 0.18212 (13) | 0.12116 (11) | 0.0572 (5) | |
C45 | 0.4181 (2) | 0.08336 (17) | 0.11236 (13) | 0.0368 (5) | |
C46 | 0.3498 (3) | 0.0099 (2) | 0.04132 (15) | 0.0581 (7) | |
H46A | 0.371962 | 0.027056 | −0.004017 | 0.087* | |
H46B | 0.262618 | 0.019558 | 0.050183 | 0.087* | |
H46C | 0.371140 | −0.063933 | 0.032166 | 0.087* | |
O7 | 0.40477 (17) | 0.66077 (12) | 0.16375 (9) | 0.0493 (5) | |
O8 | 0.46056 (17) | 0.48909 (12) | 0.11445 (10) | 0.0497 (5) | |
C47 | 0.4017 (2) | 0.56810 (17) | 0.11097 (13) | 0.0341 (5) | |
C48 | 0.3219 (3) | 0.5520 (2) | 0.03979 (14) | 0.0508 (7) | |
H48A | 0.326314 | 0.615251 | 0.025871 | 0.076* | |
H48B | 0.238031 | 0.540220 | 0.051669 | 0.076* | |
H48C | 0.350369 | 0.490185 | −0.003708 | 0.076* | |
O9 | 0.4626 (3) | 0.2741 (2) | 0.00169 (13) | 0.0817 (8) | |
H9A | 0.455 (4) | 0.342 (4) | 0.033 (3) | 0.136 (18)* | |
H9B | 0.449 (4) | 0.238 (3) | 0.032 (2) | 0.107 (15)* | |
O10 | 0.4565 (3) | 0.2236 (2) | 0.49644 (13) | 0.0767 (7) | |
H10A | 0.447 (3) | 0.187 (3) | 0.527 (2) | 0.094 (12)* | |
H10B | 0.442 (3) | 0.288 (3) | 0.527 (2) | 0.091 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0499 (14) | 0.0404 (11) | 0.0599 (14) | −0.0059 (9) | −0.0003 (10) | 0.0296 (10) |
N2 | 0.0536 (14) | 0.0351 (10) | 0.0381 (11) | 0.0032 (9) | −0.0046 (9) | 0.0154 (9) |
C1 | 0.0576 (18) | 0.0490 (14) | 0.0486 (15) | −0.0009 (12) | 0.0012 (12) | 0.0294 (12) |
C2 | 0.0546 (18) | 0.0465 (14) | 0.0435 (14) | 0.0068 (12) | 0.0079 (12) | 0.0175 (12) |
C3 | 0.0398 (15) | 0.0313 (11) | 0.0418 (13) | 0.0062 (9) | 0.0053 (10) | 0.0152 (10) |
C4 | 0.0428 (16) | 0.0356 (12) | 0.0492 (15) | −0.0014 (10) | −0.0028 (11) | 0.0148 (11) |
C5 | 0.0368 (15) | 0.0351 (12) | 0.0501 (14) | 0.0036 (10) | 0.0040 (11) | 0.0204 (11) |
C6 | 0.0561 (19) | 0.0534 (16) | 0.0516 (16) | 0.0062 (13) | 0.0005 (13) | 0.0280 (13) |
C7 | 0.052 (2) | 0.0632 (18) | 0.0568 (17) | 0.0035 (14) | −0.0099 (13) | 0.0194 (14) |
C8 | 0.054 (2) | 0.0535 (16) | 0.0666 (19) | −0.0137 (13) | −0.0072 (14) | 0.0170 (14) |
C9 | 0.0482 (18) | 0.0444 (14) | 0.0597 (17) | −0.0087 (11) | 0.0045 (13) | 0.0218 (13) |
C10 | 0.0367 (14) | 0.0324 (12) | 0.0463 (13) | 0.0047 (9) | 0.0071 (10) | 0.0169 (10) |
N3 | 0.0525 (15) | 0.0417 (12) | 0.0615 (14) | −0.0002 (10) | 0.0090 (11) | 0.0296 (10) |
N4 | 0.0584 (15) | 0.0350 (11) | 0.0520 (13) | 0.0050 (9) | −0.0072 (10) | 0.0154 (9) |
C11 | 0.0624 (19) | 0.0430 (14) | 0.0420 (14) | 0.0011 (12) | 0.0011 (12) | 0.0207 (11) |
C12 | 0.0600 (19) | 0.0484 (15) | 0.0400 (14) | 0.0129 (12) | 0.0065 (12) | 0.0148 (12) |
C13 | 0.0430 (15) | 0.0322 (12) | 0.0437 (13) | 0.0099 (10) | 0.0051 (11) | 0.0131 (10) |
C14 | 0.0462 (17) | 0.0324 (12) | 0.0577 (16) | 0.0029 (10) | −0.0016 (12) | 0.0138 (11) |
C15 | 0.0401 (15) | 0.0390 (13) | 0.0482 (14) | 0.0084 (10) | 0.0069 (11) | 0.0208 (11) |
C16 | 0.059 (2) | 0.0687 (19) | 0.0502 (16) | 0.0180 (15) | 0.0014 (13) | 0.0307 (14) |
C17 | 0.054 (2) | 0.078 (2) | 0.0608 (19) | 0.0103 (16) | −0.0148 (15) | 0.0130 (16) |
C18 | 0.050 (2) | 0.0666 (19) | 0.071 (2) | −0.0087 (14) | −0.0037 (15) | 0.0148 (16) |
C19 | 0.0457 (18) | 0.0509 (15) | 0.0606 (17) | −0.0052 (12) | 0.0125 (13) | 0.0210 (13) |
C20 | 0.0366 (15) | 0.0358 (12) | 0.0430 (13) | 0.0066 (10) | 0.0087 (10) | 0.0149 (10) |
N5 | 0.0509 (14) | 0.0278 (10) | 0.0604 (14) | 0.0041 (9) | −0.0006 (10) | 0.0121 (10) |
N6 | 0.0567 (15) | 0.0351 (11) | 0.0529 (13) | −0.0059 (9) | −0.0018 (10) | 0.0192 (10) |
C21 | 0.0594 (19) | 0.0310 (12) | 0.0456 (14) | 0.0023 (11) | 0.0013 (12) | 0.0089 (11) |
C22 | 0.0552 (18) | 0.0466 (14) | 0.0426 (14) | −0.0015 (12) | 0.0104 (12) | 0.0119 (12) |
C23 | 0.0427 (15) | 0.0335 (12) | 0.0443 (14) | −0.0038 (10) | 0.0058 (11) | 0.0160 (10) |
C24 | 0.0448 (16) | 0.0405 (13) | 0.0521 (15) | −0.0018 (11) | −0.0022 (11) | 0.0215 (12) |
C25 | 0.0379 (15) | 0.0326 (12) | 0.0530 (15) | −0.0015 (10) | 0.0035 (11) | 0.0162 (11) |
C26 | 0.056 (2) | 0.0452 (15) | 0.0574 (17) | −0.0081 (12) | −0.0026 (13) | 0.0114 (13) |
C27 | 0.059 (2) | 0.073 (2) | 0.0607 (18) | −0.0162 (15) | −0.0139 (14) | 0.0228 (16) |
C28 | 0.050 (2) | 0.075 (2) | 0.076 (2) | 0.0086 (15) | −0.0085 (15) | 0.0365 (17) |
C29 | 0.0482 (18) | 0.0483 (15) | 0.0655 (18) | 0.0134 (12) | 0.0110 (14) | 0.0237 (13) |
C30 | 0.0358 (15) | 0.0347 (12) | 0.0486 (14) | −0.0001 (9) | 0.0074 (11) | 0.0168 (10) |
N7 | 0.0509 (14) | 0.0296 (10) | 0.0623 (14) | 0.0067 (9) | 0.0055 (10) | 0.0146 (10) |
N8 | 0.0534 (14) | 0.0361 (10) | 0.0387 (11) | −0.0081 (9) | −0.0069 (9) | 0.0126 (9) |
C31 | 0.0550 (18) | 0.0375 (13) | 0.0440 (14) | −0.0028 (11) | 0.0053 (12) | 0.0046 (11) |
C32 | 0.0594 (19) | 0.0506 (15) | 0.0376 (14) | −0.0083 (12) | 0.0059 (12) | 0.0140 (12) |
C33 | 0.0386 (15) | 0.0343 (12) | 0.0419 (13) | −0.0050 (9) | 0.0040 (10) | 0.0167 (10) |
C34 | 0.0437 (16) | 0.0445 (14) | 0.0538 (15) | −0.0034 (11) | −0.0047 (11) | 0.0270 (12) |
C35 | 0.0386 (15) | 0.0332 (12) | 0.0474 (14) | −0.0019 (10) | 0.0056 (11) | 0.0146 (11) |
C36 | 0.058 (2) | 0.0460 (15) | 0.0479 (15) | −0.0137 (12) | 0.0020 (13) | 0.0085 (12) |
C37 | 0.057 (2) | 0.078 (2) | 0.0538 (17) | −0.0192 (15) | −0.0137 (14) | 0.0265 (16) |
C38 | 0.0467 (19) | 0.075 (2) | 0.0681 (19) | 0.0042 (14) | −0.0044 (14) | 0.0377 (16) |
C39 | 0.0463 (17) | 0.0464 (14) | 0.0587 (17) | 0.0109 (12) | 0.0085 (13) | 0.0223 (13) |
C40 | 0.0361 (14) | 0.0315 (11) | 0.0409 (13) | −0.0005 (9) | 0.0070 (10) | 0.0146 (10) |
O1 | 0.0616 (13) | 0.0366 (9) | 0.0447 (10) | −0.0074 (8) | −0.0071 (8) | 0.0136 (8) |
O2 | 0.0727 (14) | 0.0408 (10) | 0.0631 (12) | −0.0089 (9) | −0.0059 (9) | 0.0303 (9) |
C41 | 0.0383 (15) | 0.0369 (13) | 0.0344 (12) | −0.0009 (9) | 0.0039 (10) | 0.0151 (10) |
C42 | 0.066 (2) | 0.0651 (18) | 0.0444 (15) | 0.0148 (14) | −0.0101 (13) | 0.0130 (13) |
O3 | 0.0599 (13) | 0.0397 (9) | 0.0521 (10) | −0.0162 (8) | −0.0051 (8) | 0.0206 (8) |
O4 | 0.0597 (13) | 0.0491 (10) | 0.0419 (10) | −0.0083 (8) | −0.0024 (8) | 0.0238 (8) |
C43 | 0.0412 (15) | 0.0262 (11) | 0.0368 (12) | 0.0004 (9) | 0.0044 (10) | 0.0104 (9) |
C44 | 0.0546 (18) | 0.0466 (14) | 0.0445 (14) | −0.0088 (12) | −0.0093 (12) | 0.0111 (12) |
O5 | 0.0568 (12) | 0.0386 (9) | 0.0497 (10) | 0.0028 (8) | −0.0063 (8) | 0.0178 (8) |
O6 | 0.0701 (14) | 0.0303 (9) | 0.0703 (13) | 0.0047 (8) | −0.0038 (10) | 0.0171 (8) |
C45 | 0.0389 (15) | 0.0298 (12) | 0.0404 (13) | 0.0051 (9) | 0.0049 (10) | 0.0113 (10) |
C46 | 0.064 (2) | 0.0612 (17) | 0.0484 (16) | −0.0147 (14) | −0.0071 (13) | 0.0192 (13) |
O7 | 0.0664 (13) | 0.0353 (9) | 0.0394 (9) | 0.0087 (8) | −0.0063 (8) | 0.0054 (7) |
O8 | 0.0616 (13) | 0.0377 (9) | 0.0526 (10) | 0.0088 (8) | −0.0049 (8) | 0.0198 (8) |
C47 | 0.0395 (14) | 0.0321 (12) | 0.0330 (12) | 0.0037 (9) | 0.0034 (9) | 0.0145 (10) |
C48 | 0.0576 (19) | 0.0534 (16) | 0.0427 (14) | −0.0003 (12) | −0.0077 (12) | 0.0192 (12) |
O9 | 0.138 (2) | 0.0510 (14) | 0.0508 (13) | −0.0057 (13) | −0.0047 (13) | 0.0119 (11) |
O10 | 0.129 (2) | 0.0563 (14) | 0.0483 (13) | 0.0027 (13) | −0.0048 (12) | 0.0236 (12) |
N1—C4 | 1.362 (3) | C23—C30 | 1.430 (3) |
N1—C5 | 1.372 (3) | C24—H24 | 0.9300 |
N1—H1N | 0.8600 | C25—C26 | 1.390 (4) |
N2—C1 | 1.490 (3) | C25—C30 | 1.409 (3) |
N2—H2AN | 0.8900 | C26—C27 | 1.372 (4) |
N2—H2BN | 0.8900 | C26—H26 | 0.9300 |
N2—H2CN | 0.8900 | C27—C28 | 1.389 (4) |
C1—C2 | 1.514 (3) | C27—H27 | 0.9300 |
C1—H1A | 0.9700 | C28—C29 | 1.378 (4) |
C1—H1B | 0.9700 | C28—H28 | 0.9300 |
C2—C3 | 1.498 (3) | C29—C30 | 1.398 (3) |
C2—H2A | 0.9700 | C29—H29 | 0.9300 |
C2—H2B | 0.9700 | N7—C35 | 1.360 (3) |
C3—C4 | 1.358 (3) | N7—C34 | 1.364 (3) |
C3—C10 | 1.429 (3) | N7—H7N | 0.8600 |
C4—H4 | 0.9300 | N8—C31 | 1.490 (3) |
C5—C6 | 1.387 (3) | N8—H8AN | 0.8900 |
C5—C10 | 1.415 (3) | N8—H8BN | 0.8900 |
C6—C7 | 1.372 (4) | N8—H8CN | 0.8900 |
C6—H6 | 0.9300 | C31—C32 | 1.514 (3) |
C7—C8 | 1.395 (4) | C31—H31A | 0.9700 |
C7—H7 | 0.9300 | C31—H31B | 0.9700 |
C8—C9 | 1.367 (4) | C32—C33 | 1.499 (3) |
C8—H8 | 0.9300 | C32—H32A | 0.9700 |
C9—C10 | 1.395 (3) | C32—H32B | 0.9700 |
C9—H9 | 0.9300 | C33—C34 | 1.359 (3) |
N3—C15 | 1.365 (3) | C33—C40 | 1.431 (3) |
N3—C14 | 1.370 (3) | C34—H34 | 0.9300 |
N3—H3N | 0.8600 | C35—C36 | 1.397 (3) |
N4—C11 | 1.481 (3) | C35—C40 | 1.407 (3) |
N4—H4AN | 0.8900 | C36—C37 | 1.373 (4) |
N4—H4BN | 0.8900 | C36—H36 | 0.9300 |
N4—H4CN | 0.8900 | C37—C38 | 1.389 (4) |
C11—C12 | 1.509 (3) | C37—H37 | 0.9300 |
C11—H11A | 0.9700 | C38—C39 | 1.372 (4) |
C11—H11B | 0.9700 | C38—H38 | 0.9300 |
C12—C13 | 1.497 (3) | C39—C40 | 1.394 (3) |
C12—H12A | 0.9700 | C39—H39 | 0.9300 |
C12—H12B | 0.9700 | O1—C41 | 1.248 (3) |
C13—C14 | 1.361 (3) | O2—C41 | 1.259 (3) |
C13—C20 | 1.433 (3) | C41—C42 | 1.495 (3) |
C14—H14 | 0.9300 | C42—H42A | 0.9600 |
C15—C16 | 1.394 (4) | C42—H42B | 0.9600 |
C15—C20 | 1.412 (3) | C42—H42C | 0.9600 |
C16—C17 | 1.374 (4) | O3—C43 | 1.252 (3) |
C16—H16 | 0.9300 | O4—C43 | 1.254 (3) |
C17—C18 | 1.385 (4) | C43—C44 | 1.500 (3) |
C17—H17 | 0.9300 | C44—H44A | 0.9600 |
C18—C19 | 1.370 (4) | C44—H44B | 0.9600 |
C18—H18 | 0.9300 | C44—H44C | 0.9600 |
C19—C20 | 1.394 (3) | O5—C45 | 1.246 (3) |
C19—H19 | 0.9300 | O6—C45 | 1.263 (3) |
N5—C25 | 1.364 (3) | C45—C46 | 1.495 (3) |
N5—C24 | 1.366 (3) | C46—H46A | 0.9600 |
N5—H5N | 0.8600 | C46—H46B | 0.9600 |
N6—C21 | 1.480 (3) | C46—H46C | 0.9600 |
N6—H6AN | 0.8900 | O7—C47 | 1.253 (3) |
N6—H6BN | 0.8900 | O8—C47 | 1.247 (3) |
N6—H6CN | 0.8900 | C47—C48 | 1.501 (3) |
C21—C22 | 1.517 (3) | C48—H48A | 0.9600 |
C21—H21A | 0.9700 | C48—H48B | 0.9600 |
C21—H21B | 0.9700 | C48—H48C | 0.9600 |
C22—C23 | 1.498 (3) | O9—H9A | 0.88 (5) |
C22—H22A | 0.9700 | O9—H9B | 0.86 (4) |
C22—H22B | 0.9700 | O10—H10A | 0.88 (4) |
C23—C24 | 1.363 (3) | O10—H10B | 0.85 (4) |
C4—N1—C5 | 108.61 (19) | C21—C22—H22B | 108.8 |
C4—N1—H1N | 125.7 | H22A—C22—H22B | 107.7 |
C5—N1—H1N | 125.7 | C24—C23—C30 | 106.3 (2) |
C1—N2—H2AN | 109.5 | C24—C23—C22 | 127.0 (2) |
C1—N2—H2BN | 109.5 | C30—C23—C22 | 126.8 (2) |
H2AN—N2—H2BN | 109.5 | C23—C24—N5 | 110.4 (2) |
C1—N2—H2CN | 109.5 | C23—C24—H24 | 124.8 |
H2AN—N2—H2CN | 109.5 | N5—C24—H24 | 124.8 |
H2BN—N2—H2CN | 109.5 | N5—C25—C26 | 130.7 (2) |
N2—C1—C2 | 111.8 (2) | N5—C25—C30 | 107.7 (2) |
N2—C1—H1A | 109.3 | C26—C25—C30 | 121.6 (2) |
C2—C1—H1A | 109.3 | C27—C26—C25 | 118.1 (3) |
N2—C1—H1B | 109.3 | C27—C26—H26 | 121.0 |
C2—C1—H1B | 109.3 | C25—C26—H26 | 121.0 |
H1A—C1—H1B | 107.9 | C26—C27—C28 | 121.2 (3) |
C3—C2—C1 | 114.13 (19) | C26—C27—H27 | 119.4 |
C3—C2—H2A | 108.7 | C28—C27—H27 | 119.4 |
C1—C2—H2A | 108.7 | C29—C28—C27 | 121.3 (3) |
C3—C2—H2B | 108.7 | C29—C28—H28 | 119.4 |
C1—C2—H2B | 108.7 | C27—C28—H28 | 119.4 |
H2A—C2—H2B | 107.6 | C28—C29—C30 | 118.8 (2) |
C4—C3—C10 | 106.3 (2) | C28—C29—H29 | 120.6 |
C4—C3—C2 | 126.1 (2) | C30—C29—H29 | 120.6 |
C10—C3—C2 | 127.6 (2) | C29—C30—C25 | 119.0 (2) |
C3—C4—N1 | 110.9 (2) | C29—C30—C23 | 134.1 (2) |
C3—C4—H4 | 124.6 | C25—C30—C23 | 106.8 (2) |
N1—C4—H4 | 124.6 | C35—N7—C34 | 108.97 (19) |
N1—C5—C6 | 130.8 (2) | C35—N7—H7N | 125.5 |
N1—C5—C10 | 107.4 (2) | C34—N7—H7N | 125.5 |
C6—C5—C10 | 121.8 (2) | C31—N8—H8AN | 109.5 |
C7—C6—C5 | 117.9 (2) | C31—N8—H8BN | 109.5 |
C7—C6—H6 | 121.1 | H8AN—N8—H8BN | 109.5 |
C5—C6—H6 | 121.1 | C31—N8—H8CN | 109.5 |
C6—C7—C8 | 121.2 (3) | H8AN—N8—H8CN | 109.5 |
C6—C7—H7 | 119.4 | H8BN—N8—H8CN | 109.5 |
C8—C7—H7 | 119.4 | N8—C31—C32 | 111.9 (2) |
C9—C8—C7 | 121.2 (3) | N8—C31—H31A | 109.2 |
C9—C8—H8 | 119.4 | C32—C31—H31A | 109.2 |
C7—C8—H8 | 119.4 | N8—C31—H31B | 109.2 |
C8—C9—C10 | 119.3 (2) | C32—C31—H31B | 109.2 |
C8—C9—H9 | 120.4 | H31A—C31—H31B | 107.9 |
C10—C9—H9 | 120.4 | C33—C32—C31 | 114.23 (19) |
C9—C10—C5 | 118.6 (2) | C33—C32—H32A | 108.7 |
C9—C10—C3 | 134.5 (2) | C31—C32—H32A | 108.7 |
C5—C10—C3 | 106.8 (2) | C33—C32—H32B | 108.7 |
C15—N3—C14 | 108.9 (2) | C31—C32—H32B | 108.7 |
C15—N3—H3N | 125.5 | H32A—C32—H32B | 107.6 |
C14—N3—H3N | 125.5 | C34—C33—C40 | 106.2 (2) |
C11—N4—H4AN | 109.5 | C34—C33—C32 | 126.0 (2) |
C11—N4—H4BN | 109.5 | C40—C33—C32 | 127.7 (2) |
H4AN—N4—H4BN | 109.5 | C33—C34—N7 | 110.3 (2) |
C11—N4—H4CN | 109.5 | C33—C34—H34 | 124.8 |
H4AN—N4—H4CN | 109.5 | N7—C34—H34 | 124.8 |
H4BN—N4—H4CN | 109.5 | N7—C35—C36 | 130.6 (2) |
N4—C11—C12 | 111.9 (2) | N7—C35—C40 | 107.7 (2) |
N4—C11—H11A | 109.2 | C36—C35—C40 | 121.7 (2) |
C12—C11—H11A | 109.2 | C37—C36—C35 | 117.8 (2) |
N4—C11—H11B | 109.2 | C37—C36—H36 | 121.1 |
C12—C11—H11B | 109.2 | C35—C36—H36 | 121.1 |
H11A—C11—H11B | 107.9 | C36—C37—C38 | 121.2 (3) |
C13—C12—C11 | 113.95 (19) | C36—C37—H37 | 119.4 |
C13—C12—H12A | 108.8 | C38—C37—H37 | 119.4 |
C11—C12—H12A | 108.8 | C39—C38—C37 | 121.3 (3) |
C13—C12—H12B | 108.8 | C39—C38—H38 | 119.3 |
C11—C12—H12B | 108.8 | C37—C38—H38 | 119.3 |
H12A—C12—H12B | 107.7 | C38—C39—C40 | 119.3 (2) |
C14—C13—C20 | 106.3 (2) | C38—C39—H39 | 120.4 |
C14—C13—C12 | 126.7 (2) | C40—C39—H39 | 120.4 |
C20—C13—C12 | 127.0 (2) | C39—C40—C35 | 118.8 (2) |
C13—C14—N3 | 110.3 (2) | C39—C40—C33 | 134.4 (2) |
C13—C14—H14 | 124.8 | C35—C40—C33 | 106.7 (2) |
N3—C14—H14 | 124.8 | O1—C41—O2 | 122.8 (2) |
N3—C15—C16 | 130.4 (2) | O1—C41—C42 | 118.7 (2) |
N3—C15—C20 | 107.6 (2) | O2—C41—C42 | 118.5 (2) |
C16—C15—C20 | 122.0 (2) | C41—C42—H42A | 109.5 |
C17—C16—C15 | 117.3 (3) | C41—C42—H42B | 109.5 |
C17—C16—H16 | 121.3 | H42A—C42—H42B | 109.5 |
C15—C16—H16 | 121.3 | C41—C42—H42C | 109.5 |
C16—C17—C18 | 121.7 (3) | H42A—C42—H42C | 109.5 |
C16—C17—H17 | 119.2 | H42B—C42—H42C | 109.5 |
C18—C17—H17 | 119.2 | O3—C43—O4 | 124.2 (2) |
C19—C18—C17 | 121.1 (3) | O3—C43—C44 | 117.6 (2) |
C19—C18—H18 | 119.4 | O4—C43—C44 | 118.1 (2) |
C17—C18—H18 | 119.4 | C43—C44—H44A | 109.5 |
C18—C19—C20 | 119.5 (3) | C43—C44—H44B | 109.5 |
C18—C19—H19 | 120.2 | H44A—C44—H44B | 109.5 |
C20—C19—H19 | 120.2 | C43—C44—H44C | 109.5 |
C19—C20—C15 | 118.4 (2) | H44A—C44—H44C | 109.5 |
C19—C20—C13 | 134.8 (2) | H44B—C44—H44C | 109.5 |
C15—C20—C13 | 106.8 (2) | O5—C45—O6 | 123.2 (2) |
C25—N5—C24 | 108.81 (19) | O5—C45—C46 | 118.9 (2) |
C25—N5—H5N | 125.6 | O6—C45—C46 | 117.9 (2) |
C24—N5—H5N | 125.6 | C45—C46—H46A | 109.5 |
C21—N6—H6AN | 109.5 | C45—C46—H46B | 109.5 |
C21—N6—H6BN | 109.5 | H46A—C46—H46B | 109.5 |
H6AN—N6—H6BN | 109.5 | C45—C46—H46C | 109.5 |
C21—N6—H6CN | 109.5 | H46A—C46—H46C | 109.5 |
H6AN—N6—H6CN | 109.5 | H46B—C46—H46C | 109.5 |
H6BN—N6—H6CN | 109.5 | O8—C47—O7 | 123.9 (2) |
N6—C21—C22 | 111.64 (19) | O8—C47—C48 | 118.5 (2) |
N6—C21—H21A | 109.3 | O7—C47—C48 | 117.63 (19) |
C22—C21—H21A | 109.3 | C47—C48—H48A | 109.5 |
N6—C21—H21B | 109.3 | C47—C48—H48B | 109.5 |
C22—C21—H21B | 109.3 | H48A—C48—H48B | 109.5 |
H21A—C21—H21B | 108.0 | C47—C48—H48C | 109.5 |
C23—C22—C21 | 113.92 (19) | H48A—C48—H48C | 109.5 |
C23—C22—H22A | 108.8 | H48B—C48—H48C | 109.5 |
C21—C22—H22A | 108.8 | H9A—O9—H9B | 105 (4) |
C23—C22—H22B | 108.8 | H10A—O10—H10B | 102 (3) |
N2—C1—C2—C3 | −58.5 (3) | N6—C21—C22—C23 | −64.6 (3) |
C1—C2—C3—C4 | 103.1 (3) | C21—C22—C23—C24 | 100.7 (3) |
C1—C2—C3—C10 | −75.4 (3) | C21—C22—C23—C30 | −78.6 (3) |
C10—C3—C4—N1 | −0.3 (3) | C30—C23—C24—N5 | −0.5 (3) |
C2—C3—C4—N1 | −179.0 (2) | C22—C23—C24—N5 | −179.8 (2) |
C5—N1—C4—C3 | 0.0 (3) | C25—N5—C24—C23 | −0.1 (3) |
C4—N1—C5—C6 | −179.4 (2) | C24—N5—C25—C26 | −179.2 (3) |
C4—N1—C5—C10 | 0.2 (3) | C24—N5—C25—C30 | 0.6 (3) |
N1—C5—C6—C7 | 179.5 (2) | N5—C25—C26—C27 | 179.2 (3) |
C10—C5—C6—C7 | −0.1 (4) | C30—C25—C26—C27 | −0.6 (4) |
C5—C6—C7—C8 | −0.9 (4) | C25—C26—C27—C28 | −0.3 (4) |
C6—C7—C8—C9 | 1.2 (4) | C26—C27—C28—C29 | 0.7 (5) |
C7—C8—C9—C10 | −0.4 (4) | C27—C28—C29—C30 | −0.2 (4) |
C8—C9—C10—C5 | −0.7 (4) | C28—C29—C30—C25 | −0.7 (4) |
C8—C9—C10—C3 | −178.5 (3) | C28—C29—C30—C23 | −177.9 (3) |
N1—C5—C10—C9 | −178.8 (2) | N5—C25—C30—C29 | −178.7 (2) |
C6—C5—C10—C9 | 0.9 (3) | C26—C25—C30—C29 | 1.1 (4) |
N1—C5—C10—C3 | −0.4 (2) | N5—C25—C30—C23 | −0.9 (3) |
C6—C5—C10—C3 | 179.3 (2) | C26—C25—C30—C23 | 179.0 (2) |
C4—C3—C10—C9 | 178.4 (3) | C24—C23—C30—C29 | 178.2 (3) |
C2—C3—C10—C9 | −2.9 (4) | C22—C23—C30—C29 | −2.4 (4) |
C4—C3—C10—C5 | 0.4 (2) | C24—C23—C30—C25 | 0.8 (3) |
C2—C3—C10—C5 | 179.1 (2) | C22—C23—C30—C25 | −179.8 (2) |
N4—C11—C12—C13 | 59.5 (3) | N8—C31—C32—C33 | −56.0 (3) |
C11—C12—C13—C14 | −102.8 (3) | C31—C32—C33—C34 | 103.2 (3) |
C11—C12—C13—C20 | 78.1 (3) | C31—C32—C33—C40 | −76.4 (3) |
C20—C13—C14—N3 | 0.6 (3) | C40—C33—C34—N7 | −0.8 (3) |
C12—C13—C14—N3 | −178.7 (2) | C32—C33—C34—N7 | 179.5 (2) |
C15—N3—C14—C13 | −0.8 (3) | C35—N7—C34—C33 | 0.9 (3) |
C14—N3—C15—C16 | 179.9 (2) | C34—N7—C35—C36 | 179.4 (2) |
C14—N3—C15—C20 | 0.6 (3) | C34—N7—C35—C40 | −0.5 (3) |
N3—C15—C16—C17 | −178.2 (3) | N7—C35—C36—C37 | 178.8 (3) |
C20—C15—C16—C17 | 1.0 (4) | C40—C35—C36—C37 | −1.3 (4) |
C15—C16—C17—C18 | −0.3 (4) | C35—C36—C37—C38 | 0.3 (4) |
C16—C17—C18—C19 | −0.3 (5) | C36—C37—C38—C39 | 0.3 (5) |
C17—C18—C19—C20 | 0.2 (4) | C37—C38—C39—C40 | 0.1 (4) |
C18—C19—C20—C15 | 0.5 (4) | C38—C39—C40—C35 | −1.1 (4) |
C18—C19—C20—C13 | 178.5 (3) | C38—C39—C40—C33 | −178.9 (3) |
N3—C15—C20—C19 | 178.3 (2) | N7—C35—C40—C39 | −178.4 (2) |
C16—C15—C20—C19 | −1.1 (3) | C36—C35—C40—C39 | 1.7 (3) |
N3—C15—C20—C13 | −0.3 (2) | N7—C35—C40—C33 | 0.0 (2) |
C16—C15—C20—C13 | −179.6 (2) | C36—C35—C40—C33 | −179.9 (2) |
C14—C13—C20—C19 | −178.4 (3) | C34—C33—C40—C39 | 178.5 (3) |
C12—C13—C20—C19 | 0.9 (4) | C32—C33—C40—C39 | −1.8 (4) |
C14—C13—C20—C15 | −0.2 (2) | C34—C33—C40—C35 | 0.5 (2) |
C12—C13—C20—C15 | 179.1 (2) | C32—C33—C40—C35 | −179.8 (2) |
Cg2, Cg5, Cg8 and Cg11 are the centroids of the benzene rings C5-C10, C15-C20, C25-C30 and C35-C40, respectively. Cg3, Cg6, Cg9 and Cg12 are the centroids of the indole ring systems N1/C3-C10, N3/C13-C20, N5/C23-C30 and N7/C33-C40, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C42—H42B···Cg2 | 0.96 | 2.87 | 3.621 (3) | 135 |
C44—H44B···Cg5 | 0.96 | 2.74 | 3.550 (3) | 143 |
C46—H46B···Cg8 | 0.96 | 2.80 | 3.533 (3) | 134 |
C48—H48B···Cg11 | 0.96 | 2.78 | 3.629 (3) | 147 |
N1—H1N···O4i | 0.86 | 2.08 | 2.898 (2) | 159 |
N2—H2AN···O6 | 0.89 | 2.02 | 2.861 (3) | 156 |
N2—H2BN···O8 | 0.89 | 1.93 | 2.778 (2) | 158 |
N2—H2CN···O1 | 0.89 | 1.92 | 2.803 (2) | 169 |
N3—H3N···O2ii | 0.86 | 2.04 | 2.864 (3) | 161 |
N4—H4AN···O4 | 0.89 | 2.03 | 2.805 (3) | 145 |
N4—H4BN···O5i | 0.89 | 1.91 | 2.777 (2) | 163 |
N4—H4CN···O7ii | 0.89 | 2.45 | 3.186 (3) | 140 |
N5—H5N···O7iii | 0.86 | 2.01 | 2.839 (2) | 162 |
N6—H6AN···O4i | 0.89 | 2.57 | 3.122 (3) | 121 |
N6—H6BN···O1 | 0.89 | 1.95 | 2.828 (2) | 169 |
N6—H6CN···O5 | 0.89 | 2.07 | 2.936 (3) | 165 |
N7—H7N···O6 | 0.86 | 2.04 | 2.867 (3) | 161 |
N8—H8AN···O2 | 0.89 | 2.09 | 2.936 (3) | 157 |
N8—H8BN···O3ii | 0.89 | 1.85 | 2.734 (2) | 172 |
N8—H8CN···O7 | 0.89 | 1.87 | 2.726 (2) | 162 |
C4—H4···O5 | 0.93 | 2.40 | 3.248 (3) | 151 |
C34—H34···O1 | 0.93 | 2.46 | 3.347 (3) | 159 |
N4—H4CN···O9iv | 0.89 | 2.46 | 3.003 (3) | 120 |
O9—H9A···O8 | 0.88 (5) | 1.97 (5) | 2.840 (3) | 169 (4) |
O9—H9B···O6 | 0.86 (4) | 2.02 (4) | 2.872 (3) | 168 (4) |
N6—H6AN···O10 | 0.89 | 2.22 | 2.927 (3) | 136 |
O10—H10A···O3 | 0.88 (4) | 1.96 (4) | 2.822 (3) | 166 (3) |
O10—H10B···O2ii | 0.85 (4) | 2.07 (4) | 2.903 (3) | 169 (3) |
C9—H9···Cg12v | 0.93 | 2.93 | 3.782 (3) | 153 |
C19—H19···Cg9vi | 0.93 | 2.81 | 3.641 (3) | 149 |
C29—H29···Cg3vii | 0.93 | 2.92 | 3.736 (3) | 147 |
C37—H37···Cg6viii | 0.93 | 2.83 | 3.692 (3) | 155 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) x, y, z+1; (v) x+1, y, z; (vi) −x, −y, −z+1; (vii) x−1, y, z; (viii) −x, −y+1, −z+1. |
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