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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2021 Jan 29;77(Pt 2):195–199. doi: 10.1107/S2056989021000785

Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetra­hydro­iso­quinoline-4-carbo­nitrile

Farid N Naghiyev a, Maria M Grishina b, Victor N Khrustalev b,c, Ali N Khalilov a,d, Mehmet Akkurt e, Anzurat A Akobirshoeva f,*, İbrahim G Mamedov a
PMCID: PMC7869549  PMID: 33614153

The supra­molecular structure of the compound is stabilized by a three-dimensional array of N—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π inter­actions.

Keywords: crystal structure; cyclo­condensation product; 1,2,7,8-tetra­hydro­iso­quinoline ring system; Hirshfeld surface analysis

Abstract

In the title compound, C28H21N3O, the 1,2-di­hydro­pyridine ring of the 1,2,7,8-tetra­hydro­iso­quinoline ring system is planar as expected, while the cyclo­hexa-1,3-diene ring has a twist-boat conformation, with Cremer–Pople parameters Q T = 0.367 (2) A, θ = 117.3 (3)° and φ = 327.3 (4)°. The dihedral angles between the best planes through the iso­quinoline ring system and the three phenyl rings are 81.69 (12), 82.45 (11) and 47.36 (10)°. In the crystal, mol­ecules are linked via N—H⋯O and C—H⋯N hydrogen bonds, forming a three-dimensional network. Furthermore, the crystal packing is dominated by C—H⋯π bonds with a strong inter­action involving the phenyl H atoms. The role of the inter­molecular inter­actions in the crystal packing was clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (46.0%), C⋯H/H⋯C (35.1%) and N⋯H/H⋯N (10.5%) contacts.

Chemical context  

For many decades, considerable inter­est in organic and medicinal chemistry has been directed toward the synthesis of various biologically valuable nitro­gen heterocycles (Mamedov et al., 2019 ▸; Naghiyev, 2019 ▸; Kerru et al., 2020 ▸). They are prevalent structural motifs in many compounds, also having applications in coordination chemistry and material science (Zubkov et al., 2018 ▸; Mahmoudi et al., 2019 ▸; Velásquez et al., 2019 ▸). The majority of tetra­hydro­iso­quinoline moieties containing anti­tumor anti­biotics, such as saframycins, renieramycins, safracins, ecteinascidins, tetra­zomine, lemonomycin, dnacins and aclindomycins, have already been isolated from natural sources and reproduced applying different effective techniques (Scott & Williams, 2002 ▸).

Owing to the above-mentioned value of tetra­hydro­iso­quinolines, there have been significant developments in this class of compounds. Herein, and in the framework of our ongoing structural studies (Naghiyev et al., 2020a ▸,b ▸,c ▸), we report the crystal structure and Hirshfeld surface analysis of the title compound, 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetra­hydro­iso­quinoline-4-carbo­nitrile.graphic file with name e-77-00195-scheme1.jpg

Structural commentary  

As shown in Fig. 1 ▸, the 1,2-di­hydro­pyridine ring (N1/C1–C5) of the 1,2,7,8-tetra­hydro­iso­quinoline ring system (N1/C1–C9) is planar as expected, while the cyclo­hexa-1,3-diene ring (C4–C9) has a twist-boat conformation, with Cremer–Pople parameters Q T = 0.367 (2) Å, θ = 117.3 (3)° and φ = 327.3 (4)°. The dihedral angles between the best planes through the iso­quinoline ring system and the three phenyl rings (C11–C16, C17–C22 and C23–C28) are 81.69 (12), 82.45 (11) and 47.36 (10)°, respectively. All bond lengths (Allen et al., 1998 ▸) and bond angles are all normal.

Figure 1.

Figure 1

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The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Supra­molecular features  

In the crystal, mol­ecules are linked via N—H⋯O and C—H⋯N hydrogen bonds, forming a three-dimensional network (Table 1 ▸, Fig. 2 ▸). Furthermore, the crystal packing is dominated by C—H⋯π inter­actions with a strong involvement of the phenyl hydrogens on C13 (H13) and C26 (H26) (Table 1 ▸, Fig. 3 ▸).

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg4 and Cg5 are the centroids of the 1,2-di­hydro­pyridine ring (N1/C1–C5) and the C17–C22 and C23–C28 phenyl rings, respectively.

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2B⋯O1i 0.90 (3) 2.09 (3) 2.813 (3) 136 (3)
C7—H7B⋯N3ii 0.97 2.54 3.391 (4) 146
C13—H13⋯Cg5iii 0.93 2.74 3.576 (3) 149
C26—H26⋯Cg4iv 0.93 2.83 3.729 (3) 162
C16—H16⋯Cg5v 0.93 2.97 3.603 (3) 126
C20—H20⋯Cg1vi 0.93 2.96 3.514 (3) 120
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic; (iii) Inline graphic; (iv) Inline graphic; (v) Inline graphic; (vi) Inline graphic.

Figure 2.

Figure 2

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A view of the inter­molecular N—H⋯O and C—H⋯N hydrogen bonds of the title compound down the b axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

Figure 3.

Figure 3

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View of the C—H⋯π inter­actions of the title compound down the b axis. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (a) −1 + x, y, z; (b) 1 + x, y, z; (c) Inline graphic − x, 1 − y, −Inline graphic + z; (d) Inline graphic − x, 1 − y, Inline graphic + z; (e) Inline graphic − x, 1 − y, −Inline graphic + z; (f) Inline graphic − x, 1 − y, Inline graphic + z]. The centroids are defined in Table 1 ▸.

Hirshfeld surface analysis  

The Hirshfeld surfaces and two-dimensional fingerprint plots were calculated using CrystalExplorer (McKinnon et al., 2007 ▸). Hirshfeld surfaces enable the visualization of inter­molecular inter­actions with different colours and colour intensity representing short or long contacts and indicating the relative strength of the inter­actions. Fig. 4 ▸(a) and Fig. 4 ▸(b) show the front and back sides of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range −0.4556 to 1.6207 a.u. Here, the bright-red spots appearing near O1 and N3 result from the N2—H2B⋯O1 and C7—H7B⋯N3 inter­actions, which play a significant role in the mol­ecular packing of the title compound. The overall two-dimensional fingerprint plot for the title compound and those delineated into H⋯H, C⋯H/H⋯C, N⋯H/H⋯N and O⋯H/H⋯O contacts are illustrated in Fig. 5 ▸, together with their relative contributions to the Hirshfeld surface while details of the various contacts are given in Table 2 ▸. The percentage contributions from the different inter­atomic contacts to the Hirshfeld surfaces are as follows: H⋯H (46.0%), C⋯H/H⋯C (35.1%), N⋯H/H⋯N (10.5%) and O⋯H/H⋯O (6.5%) (Table 3 ▸). The other C⋯N/N⋯C, C⋯C and C⋯O/O⋯C contacts contribute less than 1% to the Hirshfeld surface mapping and have negligible directional impact on the mol­ecular packing (Table 3 ▸).

Figure 4.

Figure 4

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(a) Front and (b) back sides of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range −0.4556 to 1.6207 a.u.

Figure 5.

Figure 5

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Two-dimensional fingerprint plots of the title compound, showing (a) all inter­actions, and delineated into (b) H⋯H, (c) N⋯H/H⋯N, (d) C⋯H/H⋯C and (e) O⋯H/H⋯O inter­actions [d e and d i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (inter­nal) the surface, respectively].

Table 2. Summary of short inter­atomic contacts (Å) in the title compound.

Contact Distance Symmetry operation
O1⋯H25 2.88 1 + x, y, z
H27⋯H22 2.43 −Inline graphic + x, Inline graphic − y, 1 − z
H13⋯C23 2.86 Inline graphic − x, 1 − y, Inline graphic + z
H19⋯H24 2.41 Inline graphic + x, Inline graphic − y, 1 − z
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Table 3. Percentage contributions of inter­atomic contacts to the Hirshfeld surface for the title compound.

Contact Percentage contribution
H⋯H 46.0
C⋯H/H⋯C 35.1
N⋯H/H⋯N 10.5
O⋯H/H⋯O 6.5
C⋯N/N⋯C 0.9
C⋯C 0.5
C⋯O/O⋯C 0.4
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Database survey  

A survey of the Cambridge Structural Database (CSD version 5.41, update of March 2020; Groom et al., 2016 ▸) reveals five comparable tetra­hydro­iso­quinoline derivatives, 2-methyl-1,2,3,4-tetra­hydro­iso­quinoline trihydrate (KUGLIK; Lang­en­ohl et al., 2020 ▸), (1S,2R)-2-[(3R,4S)-3-methyl-4-phenyl-1,2,3,4-tetra­hydro­isoquinolin-2-yl]-1,2-di­phenyl­ethanol (POPYEB; Ben Ali & Retailleau, 2019 ▸), (3S*,4R*)-4-fluoro-3-(4-meth­oxy­phen­yl)-1-oxo-2-phenyl-1,2,3,4-tetra­hydro­iso­quinoline-4-carb­oxy­lic acid (CARCOQ; Lehmann et al., 2017 ▸), (S)-benzyl 3-phenyl­carbamoyl-1,2,3,4-tetra­hydro­iso­quinoline-2-carb­oxy­l­ate (LAQKUL; Naicker et al., 2012 ▸) and 2-[(1R,3S)-6,7-di­meth­oxy-1-phenyl-1,2,3,4-tetra­hydro­isoquinolin-3-yl]-4-phen­yl-1,3-thia­zole (AZUSOE; Pawar et al., 2011 ▸).

The compound KUGLIK co-crystallizes with three water mol­ecules in the asymmetric unit, which leads to the formation of intense hydrogen bonding in the crystal. In the crystal of POPYEB, mol­ecules are packed in a herringbone manner parallel to (103) and (10Inline graphic) via weak C—H⋯O and C—H⋯π(ring) inter­actions. In the crystal of CARCOQ, mol­ecules are linked by an O—H⋯O hydrogen bond, forming chains propagating along the a-axis direction. The chains are linked by C—H⋯F hydrogen bonds, forming layers lying parallel to the ab plane. In LAQKUL, there are two independent mol­ecules in the asymmetric unit. The heterocyclic ring assumes a twisted boat conformation and N—H⋯O inter­actions help to construct the three-dimensional network within the crystal packing. In AZUSOE, no classical hydrogen bonds nor π–π inter­actions were found in the crystal structure.

Synthesis and crystallization  

To a solution of 2-acetyl-5-oxo-N-3,5-tri­phenyl­penta­namide (5.1 mmol) in aceto­nitrile (40 ml) was added malono­nitrile (5.2 mmol). The solution was stirred for 5 min at room temperature, ethyl­enedi­amine (5.2 mmol) was added and the mixture refluxed for 4 h and cooled down to room temperature. The reaction product precipitated from the reaction mixture as pale-yellow single crystals, was collected by filtration and purified by recrystallization in ethanol/water solution (yield 70%, m.p. 554-556 K).

1H NMR (300 MHz, DMSO-d 6): 3.2 (dd, 3 J H–H =9.8 Hz, 3 J H–H = 2.9 Hz, 2H, CH2); 4.25 (dd, 3 J H–H = 9.8 Hz, 3 J H–H = 2.9 Hz, 1H, CH—Ar); 6.7 (s, 2H, NH2); 6.8 (s, 1H, CH=); 6.9–7.7 (m, 15H, arom).

13C NMR (75 MHz, DMSO-d 6): 35.17 (CH-Ar), 43.57 (CH2), 109.86 (=CH), 117.67 (=Cquat), 119.52 (CN), 125.96 (2CHarom), 126.72 (2CHarom), 126.86 (CHarom), 127.39 (CHarom), 127.99 (2CHarom), 128.66 (2CHarom), 128.89 (2CHarom), 128.89 (2CHarom), 129.21 (=Cquat), 129.56 (CHarom), 129.94 (=Cquat), 135.27 (N—Car), 139.07 (Car), 139.40 (Car.), 144.14 (=Cquat—N), 160.73 (O=Cquat—N), 167.96 (=Cquat—Ar).

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. The H atoms of the NH2 group were located in the difference-Fourier synthesis and refined isotropically with U iso(H) = 1.2U eq(N). All C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å, and with U iso(H) = 1.2U eq(C). Two reflections, (0 1 1) and (1 0 1), affected by the incident beam-stop and owing to poor agreement between observed and calculated intensities, nine outliers, (Inline graphic 9 7), (9 0 7), (0 6 5), (5 14 12), (Inline graphic 9 2), (1 0 9), (1 13 10), (Inline graphic 7 15) and (9 9 7), were omitted in the final cycles of refinement. The title compound crystallizes in a non-centrosymmetric space group, P 212121, but the absolute structure could not be determined reliably, and the Flack parameter is inconclusive {Flack x = −0.6 (9), determined using 1593 quotients [(I +) − (I −)]/[(I +) + (I −)] (Parsons et al., 2013 ▸)}.

Table 4. Experimental details.

Crystal data
Chemical formula C28H21N3O
M r 415.48
Crystal system, space group Orthorhombic, P212121
Temperature (K) 296
a, b, c (Å) 10.7038 (3), 11.6096 (4), 17.5182 (5)
V (Å3) 2176.93 (11)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.25 × 0.15 × 0.15
 
Data collection
Diffractometer Bruker D8 QUEST PHOTON-III CCD
Absorption correction Multi-scan (SADABS; Krause et al., 2015 ▸)
T min, T max 0.973, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections 39899, 7913, 4972
R int 0.081
(sin θ/λ)max (Å−1) 0.758
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.054, 0.123, 1.01
No. of reflections 7913
No. of parameters 296
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.27, −0.17
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Computer programs: APEX3 (Bruker, 2018 ▸), SAINT (Bruker, 2013 ▸), SHELXT2014/5 (Sheldrick, 2015a ▸), SHELXL2018/3 (Sheldrick, 2015b ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2020 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989021000785/vm2245sup1.cif

e-77-00195-sup1.cif (1.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021000785/vm2245Isup2.hkl

e-77-00195-Isup2.hkl (628.5KB, hkl)
Click here for additional data file. (8KB, cml)

Supporting information file. DOI: 10.1107/S2056989021000785/vm2245Isup3.cml

CCDC reference: 2058071

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Crystal data

C28H21N3O Dx = 1.268 Mg m−3
Mr = 415.48 Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121 Cell parameters from 5592 reflections
a = 10.7038 (3) Å θ = 2.3–27.1°
b = 11.6096 (4) Å µ = 0.08 mm−1
c = 17.5182 (5) Å T = 296 K
V = 2176.93 (11) Å3 Prism, pale yellow
Z = 4 0.25 × 0.15 × 0.15 mm
F(000) = 872
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Data collection

Bruker D8 QUEST PHOTON-III CCD diffractometer 4972 reflections with I > 2σ(I)
φ and ω scans Rint = 0.081
Absorption correction: multi-scan (SADABS; Krause et al., 2015) θmax = 32.6°, θmin = 2.3°
Tmin = 0.973, Tmax = 0.981 h = −16→16
39899 measured reflections k = −17→17
7913 independent reflections l = −26→26
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Refinement

Refinement on F2 Hydrogen site location: mixed
Least-squares matrix: full H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0438P)2 + 0.242P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123 (Δ/σ)max < 0.001
S = 1.01 Δρmax = 0.27 e Å−3
7913 reflections Δρmin = −0.17 e Å−3
296 parameters Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints Extinction coefficient: 0.0098 (17)
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.8603 (2) 0.5325 (2) 0.67650 (12) 0.0305 (5)
C2 0.8260 (2) 0.7274 (2) 0.72668 (12) 0.0301 (5)
C3 0.7054 (2) 0.7266 (2) 0.69663 (13) 0.0291 (5)
C4 0.66343 (19) 0.6306 (2) 0.65291 (12) 0.0267 (4)
C5 0.7394 (2) 0.53749 (19) 0.64189 (12) 0.0276 (4)
C6 0.7003 (2) 0.43797 (19) 0.59129 (13) 0.0284 (5)
H6 0.736642 0.367572 0.612719 0.034*
C7 0.5567 (2) 0.4246 (2) 0.59334 (15) 0.0331 (5)
H7A 0.531069 0.377784 0.550221 0.040*
H7B 0.533864 0.383461 0.639483 0.040*
C8 0.4857 (2) 0.5366 (2) 0.59104 (12) 0.0285 (5)
C9 0.5374 (2) 0.6316 (2) 0.62044 (12) 0.0288 (5)
H9 0.492214 0.700033 0.620253 0.035*
C10 0.6260 (2) 0.8212 (2) 0.71308 (14) 0.0343 (5)
C11 1.0205 (2) 0.6280 (2) 0.75426 (14) 0.0327 (5)
C12 1.0273 (2) 0.6001 (3) 0.83030 (15) 0.0468 (7)
H12 0.955194 0.583755 0.857910 0.056*
C13 1.1434 (3) 0.5967 (3) 0.86523 (17) 0.0564 (8)
H13 1.149044 0.579063 0.916902 0.068*
C14 1.2495 (3) 0.6189 (3) 0.82467 (18) 0.0516 (7)
H14 1.327119 0.615648 0.848401 0.062*
C15 1.2409 (2) 0.6460 (3) 0.74895 (18) 0.0580 (8)
H15 1.313123 0.661550 0.721318 0.070*
C16 1.1260 (2) 0.6505 (3) 0.71289 (15) 0.0469 (7)
H16 1.120619 0.668558 0.661272 0.056*
C17 0.7496 (2) 0.4510 (2) 0.51044 (13) 0.0298 (5)
C18 0.8123 (3) 0.3613 (2) 0.47579 (16) 0.0469 (7)
H18 0.825842 0.293484 0.502852 0.056*
C19 0.8557 (3) 0.3702 (3) 0.40138 (17) 0.0558 (8)
H19 0.898031 0.308574 0.379378 0.067*
C20 0.8370 (3) 0.4683 (3) 0.36024 (16) 0.0485 (7)
H20 0.865482 0.473690 0.310203 0.058*
C21 0.7759 (3) 0.5586 (3) 0.39356 (16) 0.0518 (7)
H21 0.762974 0.626088 0.366047 0.062*
C22 0.7328 (3) 0.5504 (2) 0.46820 (15) 0.0458 (6)
H22 0.692085 0.612929 0.490148 0.055*
C23 0.3570 (2) 0.5371 (2) 0.56106 (12) 0.0299 (5)
C24 0.2781 (2) 0.4429 (2) 0.57364 (14) 0.0357 (5)
H24 0.307748 0.379405 0.600472 0.043*
C25 0.1563 (2) 0.4429 (2) 0.54661 (15) 0.0425 (6)
H25 0.104480 0.380215 0.556168 0.051*
C26 0.1121 (2) 0.5354 (3) 0.50570 (15) 0.0458 (7)
H26 0.030803 0.534899 0.486933 0.055*
C27 0.1884 (3) 0.6286 (3) 0.49262 (16) 0.0473 (7)
H27 0.158275 0.691099 0.464940 0.057*
C28 0.3100 (2) 0.6304 (2) 0.52037 (14) 0.0384 (6)
H28 0.360334 0.694330 0.511654 0.046*
N1 0.89903 (16) 0.63210 (18) 0.71755 (11) 0.0305 (4)
N2 0.8714 (2) 0.8181 (2) 0.76538 (14) 0.0438 (6)
N3 0.5640 (2) 0.8978 (2) 0.72858 (15) 0.0528 (6)
O1 0.93170 (16) 0.44937 (15) 0.67346 (11) 0.0417 (4)
H2A 0.825 (3) 0.877 (3) 0.7691 (17) 0.050*
H2B 0.952 (3) 0.823 (3) 0.7796 (17) 0.050*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0284 (10) 0.0349 (12) 0.0283 (11) 0.0014 (10) −0.0022 (9) 0.0002 (9)
C2 0.0283 (10) 0.0354 (12) 0.0265 (11) −0.0017 (10) −0.0019 (9) −0.0015 (9)
C3 0.0273 (11) 0.0313 (11) 0.0288 (12) −0.0002 (9) −0.0019 (9) −0.0029 (9)
C4 0.0252 (10) 0.0306 (11) 0.0244 (10) −0.0010 (9) −0.0010 (8) 0.0021 (9)
C5 0.0256 (10) 0.0297 (11) 0.0275 (10) −0.0002 (9) −0.0030 (8) −0.0002 (9)
C6 0.0283 (10) 0.0258 (11) 0.0309 (11) 0.0002 (9) −0.0037 (9) 0.0008 (9)
C7 0.0314 (11) 0.0312 (12) 0.0367 (13) −0.0035 (10) 0.0012 (10) −0.0007 (10)
C8 0.0266 (10) 0.0336 (12) 0.0252 (10) −0.0015 (9) −0.0006 (8) 0.0016 (9)
C9 0.0257 (10) 0.0308 (12) 0.0297 (11) 0.0029 (9) −0.0022 (8) −0.0011 (9)
C10 0.0316 (11) 0.0380 (13) 0.0333 (12) 0.0007 (11) −0.0041 (10) −0.0063 (10)
C11 0.0272 (11) 0.0396 (12) 0.0314 (11) −0.0006 (10) −0.0050 (9) −0.0020 (10)
C12 0.0380 (13) 0.069 (2) 0.0339 (14) −0.0065 (13) −0.0054 (11) 0.0098 (13)
C13 0.0567 (18) 0.072 (2) 0.0406 (16) −0.0060 (16) −0.0210 (14) 0.0100 (14)
C14 0.0356 (13) 0.0614 (18) 0.0578 (18) 0.0037 (14) −0.0196 (13) −0.0071 (15)
C15 0.0275 (12) 0.092 (2) 0.0543 (18) −0.0056 (15) −0.0007 (12) −0.0048 (17)
C16 0.0349 (13) 0.073 (2) 0.0332 (13) −0.0020 (14) −0.0001 (11) 0.0001 (13)
C17 0.0274 (10) 0.0313 (11) 0.0308 (11) −0.0036 (10) −0.0017 (8) −0.0038 (9)
C18 0.0605 (17) 0.0344 (14) 0.0460 (15) 0.0030 (13) 0.0124 (13) −0.0011 (12)
C19 0.071 (2) 0.0434 (16) 0.0534 (17) −0.0014 (15) 0.0249 (16) −0.0146 (14)
C20 0.0507 (16) 0.0587 (18) 0.0360 (13) −0.0198 (14) 0.0086 (12) −0.0090 (13)
C21 0.0619 (19) 0.0519 (17) 0.0414 (15) 0.0014 (15) 0.0081 (13) 0.0109 (13)
C22 0.0553 (16) 0.0407 (14) 0.0413 (15) 0.0086 (13) 0.0102 (12) 0.0041 (12)
C23 0.0285 (11) 0.0344 (12) 0.0268 (10) −0.0030 (10) −0.0008 (9) −0.0031 (9)
C24 0.0324 (12) 0.0371 (13) 0.0376 (13) −0.0042 (10) −0.0010 (10) 0.0012 (11)
C25 0.0321 (13) 0.0485 (15) 0.0467 (15) −0.0094 (12) 0.0001 (10) −0.0037 (13)
C26 0.0311 (12) 0.0607 (18) 0.0456 (15) −0.0020 (13) −0.0088 (11) −0.0070 (14)
C27 0.0456 (15) 0.0501 (16) 0.0461 (15) 0.0035 (14) −0.0166 (12) 0.0061 (13)
C28 0.0372 (13) 0.0389 (13) 0.0391 (13) −0.0050 (11) −0.0069 (10) 0.0033 (11)
N1 0.0257 (9) 0.0371 (11) 0.0287 (10) −0.0004 (8) −0.0049 (7) −0.0020 (8)
N2 0.0345 (11) 0.0425 (12) 0.0545 (14) 0.0002 (10) −0.0121 (11) −0.0171 (11)
N3 0.0507 (13) 0.0523 (15) 0.0553 (16) 0.0171 (12) −0.0070 (12) −0.0123 (12)
O1 0.0358 (9) 0.0394 (10) 0.0499 (11) 0.0092 (8) −0.0108 (8) −0.0036 (9)
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Geometric parameters (Å, º)

C1—O1 1.232 (3) C14—H14 0.9300
C1—N1 1.424 (3) C15—C16 1.384 (4)
C1—C5 1.430 (3) C15—H15 0.9300
C2—N2 1.343 (3) C16—H16 0.9300
C2—N1 1.364 (3) C17—C18 1.380 (3)
C2—C3 1.395 (3) C17—C22 1.383 (4)
C3—C10 1.418 (3) C18—C19 1.388 (4)
C3—C4 1.424 (3) C18—H18 0.9300
C4—C5 1.367 (3) C19—C20 1.363 (4)
C4—C9 1.464 (3) C19—H19 0.9300
C5—C6 1.515 (3) C20—C21 1.367 (4)
C6—C17 1.519 (3) C20—H20 0.9300
C6—C7 1.545 (3) C21—C22 1.390 (4)
C6—H6 0.9800 C21—H21 0.9300
C7—C8 1.507 (3) C22—H22 0.9300
C7—H7A 0.9700 C23—C28 1.390 (3)
C7—H7B 0.9700 C23—C24 1.399 (3)
C8—C9 1.338 (3) C24—C25 1.387 (3)
C8—C23 1.475 (3) C24—H24 0.9300
C9—H9 0.9300 C25—C26 1.375 (4)
C10—N3 1.142 (3) C25—H25 0.9300
C11—C16 1.367 (3) C26—C27 1.375 (4)
C11—C12 1.373 (4) C26—H26 0.9300
C11—N1 1.451 (3) C27—C28 1.390 (4)
C12—C13 1.386 (4) C27—H27 0.9300
C12—H12 0.9300 C28—H28 0.9300
C13—C14 1.364 (4) N2—H2A 0.84 (3)
C13—H13 0.9300 N2—H2B 0.90 (3)
C14—C15 1.366 (4)
O1—C1—N1 118.5 (2) C14—C15—H15 119.6
O1—C1—C5 125.1 (2) C16—C15—H15 119.6
N1—C1—C5 116.39 (19) C11—C16—C15 119.0 (2)
N2—C2—N1 119.2 (2) C11—C16—H16 120.5
N2—C2—C3 122.1 (2) C15—C16—H16 120.5
N1—C2—C3 118.7 (2) C18—C17—C22 117.2 (2)
C2—C3—C10 118.2 (2) C18—C17—C6 120.3 (2)
C2—C3—C4 120.0 (2) C22—C17—C6 122.5 (2)
C10—C3—C4 121.8 (2) C17—C18—C19 121.3 (3)
C5—C4—C3 120.48 (19) C17—C18—H18 119.3
C5—C4—C9 120.0 (2) C19—C18—H18 119.3
C3—C4—C9 119.5 (2) C20—C19—C18 120.7 (3)
C4—C5—C1 120.7 (2) C20—C19—H19 119.7
C4—C5—C6 121.44 (19) C18—C19—H19 119.7
C1—C5—C6 117.83 (19) C19—C20—C21 119.1 (3)
C5—C6—C17 111.96 (19) C19—C20—H20 120.5
C5—C6—C7 109.75 (19) C21—C20—H20 120.5
C17—C6—C7 112.15 (19) C20—C21—C22 120.5 (3)
C5—C6—H6 107.6 C20—C21—H21 119.7
C17—C6—H6 107.6 C22—C21—H21 119.7
C7—C6—H6 107.6 C17—C22—C21 121.2 (3)
C8—C7—C6 114.47 (19) C17—C22—H22 119.4
C8—C7—H7A 108.6 C21—C22—H22 119.4
C6—C7—H7A 108.6 C28—C23—C24 118.1 (2)
C8—C7—H7B 108.6 C28—C23—C8 121.6 (2)
C6—C7—H7B 108.6 C24—C23—C8 120.3 (2)
H7A—C7—H7B 107.6 C25—C24—C23 120.9 (2)
C9—C8—C23 121.4 (2) C25—C24—H24 119.6
C9—C8—C7 119.52 (19) C23—C24—H24 119.6
C23—C8—C7 119.0 (2) C26—C25—C24 120.1 (3)
C8—C9—C4 121.6 (2) C26—C25—H25 120.0
C8—C9—H9 119.2 C24—C25—H25 120.0
C4—C9—H9 119.2 C27—C26—C25 119.8 (2)
N3—C10—C3 177.8 (3) C27—C26—H26 120.1
C16—C11—C12 121.0 (2) C25—C26—H26 120.1
C16—C11—N1 119.9 (2) C26—C27—C28 120.6 (3)
C12—C11—N1 119.1 (2) C26—C27—H27 119.7
C11—C12—C13 118.9 (3) C28—C27—H27 119.7
C11—C12—H12 120.6 C23—C28—C27 120.4 (2)
C13—C12—H12 120.6 C23—C28—H28 119.8
C14—C13—C12 120.7 (3) C27—C28—H28 119.8
C14—C13—H13 119.6 C2—N1—C1 123.46 (18)
C12—C13—H13 119.6 C2—N1—C11 119.22 (19)
C13—C14—C15 119.5 (3) C1—N1—C11 117.25 (19)
C13—C14—H14 120.2 C2—N2—H2A 117 (2)
C15—C14—H14 120.2 C2—N2—H2B 122 (2)
C14—C15—C16 120.8 (3) H2A—N2—H2B 119 (3)
N2—C2—C3—C10 −5.1 (4) C5—C6—C17—C18 129.5 (2)
N1—C2—C3—C10 173.7 (2) C7—C6—C17—C18 −106.6 (3)
N2—C2—C3—C4 177.0 (2) C5—C6—C17—C22 −51.4 (3)
N1—C2—C3—C4 −4.2 (3) C7—C6—C17—C22 72.5 (3)
C2—C3—C4—C5 1.9 (3) C22—C17—C18—C19 −0.6 (4)
C10—C3—C4—C5 −176.0 (2) C6—C17—C18—C19 178.5 (3)
C2—C3—C4—C9 −178.9 (2) C17—C18—C19—C20 −0.2 (5)
C10—C3—C4—C9 3.3 (3) C18—C19—C20—C21 0.7 (5)
C3—C4—C5—C1 2.5 (3) C19—C20—C21—C22 −0.3 (5)
C9—C4—C5—C1 −176.7 (2) C18—C17—C22—C21 1.0 (4)
C3—C4—C5—C6 −175.9 (2) C6—C17—C22—C21 −178.1 (3)
C9—C4—C5—C6 4.9 (3) C20—C21—C22—C17 −0.6 (5)
O1—C1—C5—C4 175.4 (2) C9—C8—C23—C28 38.7 (3)
N1—C1—C5—C4 −4.4 (3) C7—C8—C23—C28 −145.5 (2)
O1—C1—C5—C6 −6.1 (3) C9—C8—C23—C24 −140.8 (2)
N1—C1—C5—C6 174.06 (19) C7—C8—C23—C24 35.0 (3)
C4—C5—C6—C17 94.7 (2) C28—C23—C24—C25 −0.4 (4)
C1—C5—C6—C17 −83.7 (2) C8—C23—C24—C25 179.2 (2)
C4—C5—C6—C7 −30.5 (3) C23—C24—C25—C26 1.1 (4)
C1—C5—C6—C7 151.0 (2) C24—C25—C26—C27 −0.9 (4)
C5—C6—C7—C8 41.4 (3) C25—C26—C27—C28 0.0 (4)
C17—C6—C7—C8 −83.8 (3) C24—C23—C28—C27 −0.6 (4)
C6—C7—C8—C9 −29.4 (3) C8—C23—C28—C27 179.9 (2)
C6—C7—C8—C23 154.7 (2) C26—C27—C28—C23 0.8 (4)
C23—C8—C9—C4 177.7 (2) N2—C2—N1—C1 −179.0 (2)
C7—C8—C9—C4 1.9 (3) C3—C2—N1—C1 2.2 (3)
C5—C4—C9—C8 11.5 (3) N2—C2—N1—C11 4.2 (3)
C3—C4—C9—C8 −167.8 (2) C3—C2—N1—C11 −174.6 (2)
C16—C11—C12—C13 1.0 (4) O1—C1—N1—C2 −177.8 (2)
N1—C11—C12—C13 −179.7 (3) C5—C1—N1—C2 2.0 (3)
C11—C12—C13—C14 −1.0 (5) O1—C1—N1—C11 −0.9 (3)
C12—C13—C14—C15 0.7 (5) C5—C1—N1—C11 178.9 (2)
C13—C14—C15—C16 −0.4 (5) C16—C11—N1—C2 −100.4 (3)
C12—C11—C16—C15 −0.6 (5) C12—C11—N1—C2 80.2 (3)
N1—C11—C16—C15 −179.9 (3) C16—C11—N1—C1 82.5 (3)
C14—C15—C16—C11 0.3 (5) C12—C11—N1—C1 −96.8 (3)
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Hydrogen-bond geometry (Å, º)

Cg1, Cg4 and Cg5 are the centroids of the 1,2-dihydropyridine ring (N1/C1–C5) and the C17–C22 and C23–C28 phenyl rings, respectively.

D—H···A D—H H···A D···A D—H···A
N2—H2B···O1i 0.90 (3) 2.09 (3) 2.813 (3) 136 (3)
C7—H7B···N3ii 0.97 2.54 3.391 (4) 146
C13—H13···Cg5iii 0.93 2.74 3.576 (3) 149
C26—H26···Cg4iv 0.93 2.83 3.729 (3) 162
C16—H16···Cg5v 0.93 2.97 3.603 (3) 126
C20—H20···Cg1vi 0.93 2.96 3.514 (3) 120
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Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+3/2, −y+1, z+1/2; (iv) x−1, y, z; (v) x+1, y, z; (vi) −x+3/2, −y+1, z−1/2.

Funding Statement

This work was funded by Baku State University grant . Ministry of Education and Science of the Russian Federation grant 075–03-2020-223 (FSSF-2020–0017).

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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. DOI: 10.1107/S2056989021000785/vm2245sup1.cif

e-77-00195-sup1.cif (1.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021000785/vm2245Isup2.hkl

e-77-00195-Isup2.hkl (628.5KB, hkl)
Click here for additional data file. (8KB, cml)

Supporting information file. DOI: 10.1107/S2056989021000785/vm2245Isup3.cml

CCDC reference: 2058071

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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