In the title compound, the indole ring system makes a dihedral angle of 63.56 (8)° with the plane of the anthracene ring. The conformation about the C=N bond of the –CH2–CH2–N=CH– bridge linking the two units is E. In the crystal, the indole H atom is involved in an intermolecular N—H⋯π interaction with the benzene ring of the indole group, leading to the formation of chains along [010].
Keywords: crystal structure, anthracene, indole, Schiff base, tryptamine, methanamine, N—H⋯π interactions, C—H⋯π interactions
Abstract
The title compound, C25H20N2, (I), was synthesized from the condensation reaction of anthracene-9-carbaldehyde and tryptamine in dry ethanol. The indole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 63.56 (8)° with the anthracene ring (r.m.s. deviation = 0.023 Å). There is a short intramolecular C—H⋯N interaction present, and a C—H⋯π interaction involving the two ring systems. In the crystal, the indole H atom forms an intermolecular N—H⋯π interaction, linking molecules to form chains along the b-axis direction. There are also C—H⋯π interactions present, involving the central and terminal rings of the anthracene unit, linking the chains to form an overall two-dimensional layered structure, with the layers parallel to the bc plane. The density functional theory (DFT) optimized structure, at the B3LYP/6-311 G(d,p) level, is compared with the experimentally determined molecular structure in the solid state.
Chemical context
Tryptamine is a biogenic serotonin-related indoamine and is the decarboxylation product of the amino acid tryptophan. 2-(1H-Indol-3-yl)ethanamine 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 ▸). There are seven known families of serotonin receptors, which are tryptamine derivatives. 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-methyl-d-aspartate receptor (NMDAR; Worthen et al., 2001 ▸). Indole and its derivatives are secondary metabolites that are present in most plants (such as unripe bananas, broccoli and clove), almost all flower oils (e.g. 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 present work is part of an ongoing structural study of Schiff bases and their utilization in the synthesis of new organic and polynuclear coordination compounds, and their application in fluorescence sensors (Faizi & Sen, 2014 ▸; Faizi et al., 2016 ▸). We report herein the crystal structure of (E)-N-[2-(1H-indol-3-yl)ethyl]-1-(anthracen-9-yl)methanimine, (I), and its DFT computational calculation. Calculations by density functional theory (DFT) on (I), carried out at the B3LYP/6-311 G(d,p) level, are compared with the experimentally determined molecular structure in the solid state.
Structural commentary
The molecular structure of compound (I) is illustrated in Fig. 1 ▸. The molecule adopts a nonplanar geometry, with the dihedral angle between the planes of the indole and anthracene rings being 63.56 (8)°. The conformation about the azomethine C15=N1 bond [1.272 (10) Å] is E, with the C14—N2—C12—C13 torsion angle being 179.0 (1)°. The molecule is stabilized by a weak intramolecular hydrogen bond (C12—H12⋯N1) and a C—H⋯π interaction (C2—H2⋯Cg5; Cg5 is the centroid of the C19–C24 ring); see Table 1 ▸.
Figure 1.
The molecular structure of compound (I), with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Table 1. Hydrogen-bond geometry (Å, °).
Cg3, Cg4 and Cg5 are the centroids rings C1/C6–C8/C13/C14, C8–C13 and C19–C24, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C12—H12⋯N1 | 0.93 | 2.36 | 2.9845 (2) | 124 |
| C2—H2⋯Cg5 | 0.93 | 2.77 | 3.5505 (2) | 142 |
| N2—H2A⋯Cg5i | 0.86 | 2.59 | 3.1855 (2) | 127 |
| C7—H7⋯Cg4ii | 0.93 | 2.75 | 3.5777 (2) | 148 |
| C9—H9⋯Cg3ii | 0.93 | 2.73 | 3.5077 (2) | 142 |
| C16—H16A⋯Cg3iii | 0.97 | 2.86 | 3.5375 (2) | 128 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Supramolecular features
In the crystal, the indole H atom forms an intermolecular N—H⋯π interaction, linking molecules to form chains along the b-axis direction (Fig. 2 ▸ and Table 1 ▸). There are also C—H⋯π interactions present, involving the central ring and terminal rings of the anthracene unit, linking the chains to form layers parallel to the bc plane (Fig. 2 ▸ and Table 1 ▸).
Figure 2.
A view along the a axis of the crystal packing of compound (I), showing the layer-like structure. Weak N—H⋯π and C—H⋯π interactions are shown as blue dashed lines (see Table 1 ▸).
Database survey
A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2017; Groom et al., 2016 ▸) revealed the structures of several similar compounds containing a phenol group [(II) (CSD refcode FAJVIV; Rodriguez et al., 1987 ▸) and (III) (TANNOL; Ishida et al., 1992 ▸)] and nitrobenzene moieties [(IV), GEYPEF; Törnroos, 1988 ▸]. All compounds are 2-indole-substituted derivatives which have two aromatic units linked via an aliphatic chain. In (I), the dihedral angle between indole and anthracene rings is 63.56 (8)°, which is similar for (III) and (IV), viz. 71.52 and 64.21°, respectively. In compounds (I) and (II), the conformation about the azomethine C15=N1 bond is E.
DFT study
Calculations by density functional theory DFT-B3LYP, with basis set 6-311 G(d,p), of bond lengths and angles were performed. These values are compared with the experimental values for the title system (see Table 2 ▸). From these results we can conclude that basis set 6-311 G(d,p) is better suited in its approach to the experimental data.
Table 2. Comparison of selected geometric data for (I) (Å, °) from X-ray and calculated (DFT) data.
| X-ray | B3LYP/6–311G(d,p) | |
|---|---|---|
| N1—C15 | 1.272 (3) | 1.271 |
| N1—C16 | 1.468 (4) | 1.466 |
| C16—C17 | 1.528 (4) | 1.531 |
| C17—C18 | 1.499 (4) | 1.494 |
| C15—C14 | 1.479 (4) | 1.494 |
| C25—N2 | 1.372 (3) | 1.369 |
| N2—C24 | 1.371 (4) | 1.371 |
| C16—N1—C15 | 115.2 (2) | 115.31 |
| N1—C16—C17 | 110.4 (2) | 110.50 |
| N1—C15—C14 | 126.3 (3) | 126.16 |
| C16—C17—C18 | 112.2 (2) | 112.27 |
The LUMO and HOMO orbital energy parameters are considerably answerable for the charge transfer, chemical reactivity and kinetic/thermodynamic stability of (I). The DFT study of (I) revealed that the HOMO and LUMO are localized in the plane extending from the whole anthracene ring to the indole ring, and electron distribution of the HOMO-1, HOMO, LUMO and LUMO+1 energy levels are shown in Fig. 3 ▸. The molecular orbital of HOMO contains both σ and π character, whereas HOMO-1 is dominated by π-orbital density. The LUMO is mainly composed of σ density, while LUMO+1 has both σ and π electronic density. The HOMO–LUMO gap for (I) was found to be 0.12325 a.u. and the frontier molecular orbital energies, E HOMO and E LUMO, were found to be −0.196412 and −0.07087 a.u., respectively.
Figure 3.
Electron distribution of the HOMO-1, HOMO, LUMO and LUMO+1 energy levels for compound (I).
Synthesis and crystallization
80 mg (0.435 mmol) of 2-(1H-indol-3-yl)ethanamine (tryptamine) were dissolved in 10 ml of absolute ethanol. To this solution, 89 mg (0.434 mmol) of anthracene-9-carbaldehyde in 5 ml of absolute ethanol were added dropwise under stirring. The mixture was stirred for 10 min, two drops of glacial acetic acid were added and the mixture was refluxed for a further 2 h. The resulting yellow precipitate was recovered by filtration, washed several times with small portions of ice-cold ethanol and then with diethyl ether to give 140 mg (87%) of compound (I). Dark-yellow block-like crystals suitable for X-ray analysis were obtained within 3 d by slow evaporation of a solution in methanol.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. The N—H H atom was located from a difference-Fourier map and constrained to ride on the parent atom: N—H = 0.86 Å and U iso(H) = 1.2U eq(N). All C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and U iso(H) = 1.2U eq(C).
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | C25H20N2 |
| M r | 348.43 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 100 |
| a, b, c (Å) | 6.0044 (3), 16.4721 (7), 17.8957 (9) |
| V (Å3) | 1769.98 (15) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.08 |
| Crystal size (mm) | 0.20 × 0.15 × 0.13 |
| Data collection | |
| Diffractometer | Bruker SMART APEX CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2003 ▸) |
| T min, T max | 0.875, 0.990 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 14169, 3127, 2577 |
| R int | 0.064 |
| (sin θ/λ)max (Å−1) | 0.596 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.041, 0.093, 1.04 |
| No. of reflections | 3127 |
| No. of parameters | 245 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.15, −0.20 |
| Absolute structure | Refined as an inversion twin |
The DFT quantum-chemical calculations were performed at the B3LYP/6-311 G(d,p) level (Becke, 1993 ▸; Lee et al., 2003 ▸) as implemented in GAUSSIAN09 (Frisch et al., 2009 ▸). DFT structure optimization of (I) was performed starting from the X-ray geometry.
Supplementary Material
Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989017011483/su5387sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017011483/su5387Isup2.hkl
CCDC reference: 1537222
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are grateful to the Ondokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, Turkey, for X-ray data collection, and Department of Chemistry, National Taras Shevchenko University of Kiev.
supplementary crystallographic information
Crystal data
| C25H20N2 | Dx = 1.308 Mg m−3 |
| Mr = 348.43 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, P212121 | Cell parameters from 5148 reflections |
| a = 6.0044 (3) Å | θ = 2.6–27.4° |
| b = 16.4721 (7) Å | µ = 0.08 mm−1 |
| c = 17.8957 (9) Å | T = 100 K |
| V = 1769.98 (15) Å3 | Needle, yellow |
| Z = 4 | 0.20 × 0.15 × 0.13 mm |
| F(000) = 736 |
Data collection
| Bruker SMART APEX CCD diffractometer | 3127 independent reflections |
| Radiation source: fine-focus sealed tube | 2577 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.064 |
| ω scans | θmax = 25.1°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −7→7 |
| Tmin = 0.875, Tmax = 0.990 | k = −19→19 |
| 14169 measured reflections | l = −21→21 |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 3127 reflections | Δρmax = 0.15 e Å−3 |
| 245 parameters | Δρmin = −0.20 e Å−3 |
| 0 restraints | Absolute structure: Refined as an inversion twin |
| Primary atom site location: structure-invariant direct methods |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.9441 (4) | 0.37168 (13) | 0.28719 (12) | 0.0239 (6) | |
| N2 | 0.6749 (4) | 0.30313 (14) | 0.06673 (12) | 0.0282 (6) | |
| H2A | 0.546902 | 0.303463 | 0.045136 | 0.034* | |
| C18 | 0.9807 (5) | 0.34812 (16) | 0.12665 (15) | 0.0239 (7) | |
| C1 | 0.5718 (5) | 0.20309 (15) | 0.32067 (14) | 0.0199 (6) | |
| C8 | 0.3608 (5) | 0.30172 (16) | 0.42939 (14) | 0.0216 (6) | |
| C15 | 0.8796 (5) | 0.30043 (16) | 0.30408 (14) | 0.0219 (6) | |
| H15 | 0.975892 | 0.257990 | 0.292647 | 0.026* | |
| C13 | 0.5640 (5) | 0.32872 (15) | 0.39461 (15) | 0.0216 (6) | |
| C14 | 0.6662 (5) | 0.27861 (15) | 0.34017 (14) | 0.0206 (6) | |
| C7 | 0.2732 (5) | 0.22659 (16) | 0.41038 (14) | 0.0235 (7) | |
| H7 | 0.144366 | 0.208937 | 0.434185 | 0.028* | |
| C9 | 0.2567 (5) | 0.35163 (17) | 0.48380 (15) | 0.0265 (7) | |
| H9 | 0.124712 | 0.334465 | 0.505954 | 0.032* | |
| C19 | 1.0013 (5) | 0.26179 (15) | 0.11461 (15) | 0.0227 (7) | |
| C6 | 0.3713 (5) | 0.17673 (16) | 0.35700 (14) | 0.0226 (7) | |
| C2 | 0.6601 (5) | 0.15155 (15) | 0.26395 (14) | 0.0247 (7) | |
| H2 | 0.788158 | 0.167424 | 0.238604 | 0.030* | |
| C5 | 0.2749 (5) | 0.10058 (16) | 0.33667 (15) | 0.0274 (7) | |
| H5 | 0.146320 | 0.083137 | 0.360777 | 0.033* | |
| C20 | 1.1624 (5) | 0.20388 (17) | 0.13290 (15) | 0.0256 (7) | |
| H20 | 1.293314 | 0.219244 | 0.156804 | 0.031* | |
| C24 | 0.8068 (5) | 0.23616 (17) | 0.07725 (15) | 0.0250 (7) | |
| C23 | 0.7688 (5) | 0.15516 (17) | 0.05852 (15) | 0.0267 (7) | |
| H23 | 0.639991 | 0.139260 | 0.033642 | 0.032* | |
| C3 | 0.5619 (5) | 0.07970 (16) | 0.24594 (16) | 0.0276 (7) | |
| H3 | 0.624024 | 0.047503 | 0.208676 | 0.033* | |
| C4 | 0.3669 (5) | 0.05321 (16) | 0.28300 (15) | 0.0292 (7) | |
| H4 | 0.302371 | 0.003680 | 0.270620 | 0.035* | |
| C12 | 0.6514 (5) | 0.40513 (15) | 0.41843 (15) | 0.0260 (7) | |
| H12 | 0.783119 | 0.424184 | 0.397451 | 0.031* | |
| C11 | 0.5466 (5) | 0.45039 (17) | 0.47086 (15) | 0.0294 (7) | |
| H11 | 0.607818 | 0.499841 | 0.485263 | 0.035* | |
| C25 | 0.7808 (5) | 0.36954 (17) | 0.09638 (15) | 0.0279 (7) | |
| H25 | 0.723985 | 0.422058 | 0.095887 | 0.033* | |
| C16 | 1.1623 (5) | 0.37629 (16) | 0.25049 (15) | 0.0257 (7) | |
| H16A | 1.234310 | 0.323625 | 0.252515 | 0.031* | |
| H16B | 1.255871 | 0.414955 | 0.276677 | 0.031* | |
| C10 | 0.3465 (5) | 0.42396 (17) | 0.50402 (16) | 0.0293 (7) | |
| H10 | 0.276083 | 0.456023 | 0.539681 | 0.035* | |
| C22 | 0.9296 (5) | 0.09975 (18) | 0.07835 (16) | 0.0312 (7) | |
| H22 | 0.908244 | 0.045184 | 0.067111 | 0.037* | |
| C17 | 1.1358 (5) | 0.40255 (16) | 0.16908 (15) | 0.0268 (7) | |
| H17A | 1.079262 | 0.457682 | 0.167552 | 0.032* | |
| H17B | 1.280575 | 0.402183 | 0.145020 | 0.032* | |
| C21 | 1.1245 (5) | 0.12360 (16) | 0.11501 (16) | 0.0306 (7) | |
| H21 | 1.230368 | 0.084699 | 0.127540 | 0.037* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0244 (13) | 0.0239 (13) | 0.0233 (13) | −0.0025 (11) | −0.0001 (11) | 0.0016 (10) |
| N2 | 0.0235 (13) | 0.0334 (14) | 0.0277 (12) | 0.0037 (13) | −0.0039 (11) | 0.0010 (11) |
| C18 | 0.0264 (17) | 0.0259 (16) | 0.0194 (14) | 0.0018 (14) | 0.0041 (13) | 0.0033 (12) |
| C1 | 0.0216 (15) | 0.0179 (14) | 0.0201 (14) | 0.0003 (13) | −0.0036 (12) | 0.0038 (12) |
| C8 | 0.0233 (16) | 0.0231 (15) | 0.0184 (13) | 0.0026 (15) | −0.0044 (12) | 0.0048 (12) |
| C15 | 0.0233 (16) | 0.0198 (15) | 0.0225 (14) | 0.0034 (14) | −0.0035 (12) | −0.0026 (12) |
| C13 | 0.0240 (15) | 0.0208 (15) | 0.0201 (15) | 0.0008 (13) | −0.0051 (12) | 0.0042 (11) |
| C14 | 0.0213 (15) | 0.0215 (15) | 0.0190 (13) | 0.0002 (13) | −0.0038 (12) | 0.0053 (11) |
| C7 | 0.0215 (15) | 0.0280 (17) | 0.0210 (15) | 0.0002 (13) | −0.0001 (12) | 0.0068 (12) |
| C9 | 0.0256 (16) | 0.0310 (18) | 0.0230 (16) | 0.0052 (15) | 0.0006 (13) | 0.0040 (13) |
| C19 | 0.0260 (17) | 0.0246 (16) | 0.0177 (14) | −0.0010 (14) | 0.0037 (13) | −0.0001 (12) |
| C6 | 0.0238 (16) | 0.0259 (16) | 0.0179 (15) | −0.0011 (14) | −0.0046 (12) | 0.0048 (11) |
| C2 | 0.0244 (15) | 0.0245 (15) | 0.0252 (15) | 0.0009 (14) | 0.0032 (13) | 0.0041 (12) |
| C5 | 0.0305 (17) | 0.0260 (16) | 0.0257 (15) | −0.0071 (15) | −0.0019 (13) | 0.0036 (13) |
| C20 | 0.0228 (15) | 0.0287 (16) | 0.0253 (15) | −0.0012 (15) | 0.0002 (13) | −0.0008 (13) |
| C24 | 0.0254 (16) | 0.0301 (16) | 0.0193 (14) | 0.0014 (14) | 0.0026 (13) | 0.0027 (12) |
| C23 | 0.0252 (17) | 0.0345 (18) | 0.0202 (14) | −0.0052 (15) | −0.0006 (12) | −0.0011 (13) |
| C3 | 0.0342 (18) | 0.0203 (15) | 0.0283 (16) | 0.0027 (15) | 0.0020 (14) | 0.0005 (12) |
| C4 | 0.0359 (18) | 0.0233 (16) | 0.0284 (16) | −0.0070 (15) | −0.0023 (15) | 0.0015 (13) |
| C12 | 0.0274 (16) | 0.0237 (15) | 0.0270 (15) | −0.0007 (15) | −0.0010 (14) | 0.0035 (12) |
| C11 | 0.0409 (19) | 0.0211 (15) | 0.0262 (16) | −0.0018 (15) | −0.0046 (14) | −0.0021 (13) |
| C25 | 0.0339 (18) | 0.0250 (16) | 0.0247 (15) | 0.0030 (15) | 0.0034 (14) | 0.0029 (12) |
| C16 | 0.0235 (15) | 0.0214 (14) | 0.0323 (16) | −0.0059 (14) | −0.0021 (14) | −0.0005 (12) |
| C10 | 0.0371 (18) | 0.0284 (17) | 0.0223 (14) | 0.0081 (16) | 0.0001 (15) | −0.0008 (12) |
| C22 | 0.0411 (19) | 0.0263 (16) | 0.0264 (16) | −0.0058 (16) | 0.0035 (15) | −0.0029 (13) |
| C17 | 0.0267 (16) | 0.0208 (15) | 0.0328 (16) | −0.0011 (14) | 0.0063 (14) | 0.0026 (13) |
| C21 | 0.0352 (18) | 0.0270 (17) | 0.0296 (16) | 0.0055 (15) | 0.0037 (15) | 0.0014 (13) |
Geometric parameters (Å, º)
| N1—C15 | 1.272 (3) | C2—H2 | 0.9300 |
| N1—C16 | 1.468 (4) | C5—C4 | 1.355 (4) |
| N2—C24 | 1.371 (4) | C5—H5 | 0.9300 |
| N2—C25 | 1.372 (3) | C20—C21 | 1.380 (4) |
| N2—H2A | 0.8600 | C20—H20 | 0.9300 |
| C18—C25 | 1.363 (4) | C24—C23 | 1.395 (4) |
| C18—C19 | 1.444 (3) | C23—C22 | 1.375 (4) |
| C18—C17 | 1.499 (4) | C23—H23 | 0.9300 |
| C1—C14 | 1.411 (4) | C3—C4 | 1.415 (4) |
| C1—C2 | 1.426 (3) | C3—H3 | 0.9300 |
| C1—C6 | 1.436 (4) | C4—H4 | 0.9300 |
| C8—C7 | 1.387 (4) | C12—C11 | 1.354 (4) |
| C8—C9 | 1.420 (4) | C12—H12 | 0.9300 |
| C8—C13 | 1.440 (4) | C11—C10 | 1.409 (4) |
| C15—C14 | 1.479 (4) | C11—H11 | 0.9300 |
| C15—H15 | 0.9300 | C25—H25 | 0.9300 |
| C13—C14 | 1.417 (4) | C16—C17 | 1.528 (4) |
| C13—C12 | 1.429 (4) | C16—H16A | 0.9700 |
| C7—C6 | 1.391 (4) | C16—H16B | 0.9700 |
| C7—H7 | 0.9300 | C10—H10 | 0.9300 |
| C9—C10 | 1.357 (4) | C22—C21 | 1.398 (4) |
| C9—H9 | 0.9300 | C22—H22 | 0.9300 |
| C19—C20 | 1.397 (4) | C17—H17A | 0.9700 |
| C19—C24 | 1.411 (4) | C17—H17B | 0.9700 |
| C6—C5 | 1.428 (4) | C21—H21 | 0.9300 |
| C2—C3 | 1.361 (4) | ||
| C15—N1—C16 | 115.2 (2) | N2—C24—C23 | 130.0 (3) |
| C24—N2—C25 | 108.7 (2) | N2—C24—C19 | 107.6 (2) |
| C24—N2—H2A | 125.7 | C23—C24—C19 | 122.4 (3) |
| C25—N2—H2A | 125.7 | C22—C23—C24 | 117.3 (3) |
| C25—C18—C19 | 105.7 (3) | C22—C23—H23 | 121.4 |
| C25—C18—C17 | 126.4 (2) | C24—C23—H23 | 121.4 |
| C19—C18—C17 | 127.7 (3) | C2—C3—C4 | 121.1 (3) |
| C14—C1—C2 | 123.5 (2) | C2—C3—H3 | 119.5 |
| C14—C1—C6 | 119.4 (2) | C4—C3—H3 | 119.5 |
| C2—C1—C6 | 117.0 (2) | C5—C4—C3 | 119.5 (3) |
| C7—C8—C9 | 121.2 (3) | C5—C4—H4 | 120.3 |
| C7—C8—C13 | 119.4 (2) | C3—C4—H4 | 120.3 |
| C9—C8—C13 | 119.4 (2) | C11—C12—C13 | 121.4 (3) |
| N1—C15—C14 | 126.3 (3) | C11—C12—H12 | 119.3 |
| N1—C15—H15 | 116.9 | C13—C12—H12 | 119.3 |
| C14—C15—H15 | 116.9 | C12—C11—C10 | 121.2 (3) |
| C14—C13—C12 | 124.0 (3) | C12—C11—H11 | 119.4 |
| C14—C13—C8 | 119.0 (2) | C10—C11—H11 | 119.4 |
| C12—C13—C8 | 117.0 (2) | C18—C25—N2 | 110.8 (2) |
| C1—C14—C13 | 120.7 (2) | C18—C25—H25 | 124.6 |
| C1—C14—C15 | 117.0 (2) | N2—C25—H25 | 124.6 |
| C13—C14—C15 | 122.3 (2) | N1—C16—C17 | 110.4 (2) |
| C8—C7—C6 | 122.3 (3) | N1—C16—H16A | 109.6 |
| C8—C7—H7 | 118.8 | C17—C16—H16A | 109.6 |
| C6—C7—H7 | 118.8 | N1—C16—H16B | 109.6 |
| C10—C9—C8 | 121.1 (3) | C17—C16—H16B | 109.6 |
| C10—C9—H9 | 119.5 | H16A—C16—H16B | 108.1 |
| C8—C9—H9 | 119.5 | C9—C10—C11 | 119.9 (3) |
| C20—C19—C24 | 118.7 (2) | C9—C10—H10 | 120.1 |
| C20—C19—C18 | 134.2 (3) | C11—C10—H10 | 120.1 |
| C24—C19—C18 | 107.1 (2) | C23—C22—C21 | 121.5 (3) |
| C7—C6—C5 | 121.5 (2) | C23—C22—H22 | 119.3 |
| C7—C6—C1 | 119.2 (2) | C21—C22—H22 | 119.3 |
| C5—C6—C1 | 119.3 (2) | C18—C17—C16 | 112.2 (2) |
| C3—C2—C1 | 121.7 (3) | C18—C17—H17A | 109.2 |
| C3—C2—H2 | 119.2 | C16—C17—H17A | 109.2 |
| C1—C2—H2 | 119.2 | C18—C17—H17B | 109.2 |
| C4—C5—C6 | 121.4 (3) | C16—C17—H17B | 109.2 |
| C4—C5—H5 | 119.3 | H17A—C17—H17B | 107.9 |
| C6—C5—H5 | 119.3 | C20—C21—C22 | 121.1 (3) |
| C21—C20—C19 | 119.1 (3) | C20—C21—H21 | 119.5 |
| C21—C20—H20 | 120.5 | C22—C21—H21 | 119.5 |
| C19—C20—H20 | 120.5 | ||
| C16—N1—C15—C14 | −179.0 (2) | C7—C6—C5—C4 | 177.9 (3) |
| C7—C8—C13—C14 | 1.7 (3) | C1—C6—C5—C4 | −1.0 (4) |
| C9—C8—C13—C14 | −179.8 (2) | C24—C19—C20—C21 | −1.1 (4) |
| C7—C8—C13—C12 | −177.6 (2) | C18—C19—C20—C21 | 177.4 (3) |
| C9—C8—C13—C12 | 0.9 (3) | C25—N2—C24—C23 | 178.3 (3) |
| C2—C1—C14—C13 | 176.9 (2) | C25—N2—C24—C19 | −0.1 (3) |
| C6—C1—C14—C13 | −0.5 (4) | C20—C19—C24—N2 | 179.1 (2) |
| C2—C1—C14—C15 | −5.9 (4) | C18—C19—C24—N2 | 0.2 (3) |
| C6—C1—C14—C15 | 176.6 (2) | C20—C19—C24—C23 | 0.6 (4) |
| C12—C13—C14—C1 | 178.7 (2) | C18—C19—C24—C23 | −178.3 (3) |
| C8—C13—C14—C1 | −0.5 (4) | N2—C24—C23—C22 | −177.8 (3) |
| C12—C13—C14—C15 | 1.8 (4) | C19—C24—C23—C22 | 0.3 (4) |
| C8—C13—C14—C15 | −177.5 (2) | C1—C2—C3—C4 | 0.1 (4) |
| N1—C15—C14—C1 | 147.8 (3) | C6—C5—C4—C3 | −0.3 (4) |
| N1—C15—C14—C13 | −35.1 (4) | C2—C3—C4—C5 | 0.8 (4) |
| C9—C8—C7—C6 | 179.6 (2) | C14—C13—C12—C11 | −179.9 (3) |
| C13—C8—C7—C6 | −1.9 (4) | C8—C13—C12—C11 | −0.6 (4) |
| C7—C8—C9—C10 | 177.9 (2) | C13—C12—C11—C10 | −0.1 (4) |
| C13—C8—C9—C10 | −0.6 (4) | C19—C18—C25—N2 | 0.3 (3) |
| C25—C18—C19—C20 | −178.9 (3) | C17—C18—C25—N2 | −175.1 (2) |
| C17—C18—C19—C20 | −3.6 (5) | C24—N2—C25—C18 | −0.2 (3) |
| C25—C18—C19—C24 | −0.3 (3) | C15—N1—C16—C17 | 111.3 (3) |
| C17—C18—C19—C24 | 175.0 (3) | C8—C9—C10—C11 | −0.1 (4) |
| C8—C7—C6—C5 | −178.2 (2) | C12—C11—C10—C9 | 0.5 (4) |
| C8—C7—C6—C1 | 0.8 (4) | C24—C23—C22—C21 | −0.7 (4) |
| C14—C1—C6—C7 | 0.5 (4) | C25—C18—C17—C16 | 115.4 (3) |
| C2—C1—C6—C7 | −177.2 (2) | C19—C18—C17—C16 | −59.1 (4) |
| C14—C1—C6—C5 | 179.4 (2) | N1—C16—C17—C18 | −55.6 (3) |
| C2—C1—C6—C5 | 1.8 (4) | C19—C20—C21—C22 | 0.7 (4) |
| C14—C1—C2—C3 | −178.9 (3) | C23—C22—C21—C20 | 0.2 (4) |
| C6—C1—C2—C3 | −1.3 (4) |
Hydrogen-bond geometry (Å, º)
Cg3, Cg4 and Cg5 are the centroids rings C1/C6–C8/C13/C14, C8–C13 and C19–C24, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12···N1 | 0.93 | 2.36 | 2.9845 (2) | 124 |
| C2—H2···Cg5 | 0.93 | 2.77 | 3.5505 (2) | 142 |
| N2—H2A···Cg5i | 0.86 | 2.59 | 3.1855 (2) | 127 |
| C7—H7···Cg4ii | 0.93 | 2.75 | 3.5777 (2) | 148 |
| C9—H9···Cg3ii | 0.93 | 2.73 | 3.5077 (2) | 142 |
| C16—H16A···Cg3iii | 0.97 | 2.86 | 3.5375 (2) | 128 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1, y, z.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989017011483/su5387sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017011483/su5387Isup2.hkl
CCDC reference: 1537222
Additional supporting information: crystallographic information; 3D view; checkCIF report