research communications
H-3,8-methanopyrano[3,2-c]pyridine-3,4a-dicarbonitrile N,N-dimethylformamide monosolvate
and Hirshfeld surface analysis of 2,5-diimino-8a-methyl-4,9-bis(4-methylphenyl)-7-oxo-6-phenyl-decahydro-2aDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148, Baku, Azerbaijan, bPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St.6, Moscow, 117198, Russian Federation, cN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, e"Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan, and fDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np
In the title compound, C32H29N5O2·C3H7NO, the bicyclo[3.3.1]nonane ring system adopts a half-chair/twist-boat conformation, with the phenyl rings in equatorial orientations with respect to the piperidine ring. The two oxane rings of the 2-oxabicyclo[2.2.2]octane ring system exhibit a distorted boat conformation. Intermolecular C—H⋯O and C—H⋯N hydrogen bonds connect the molecules in the crystal, generating layers extending parallel to (100). These layers are connected by C—H⋯π interactions. A Hirshfeld surface analysis was performed to quantify the contributions of the different intermolecular interactions, indicating that the most important contributions to the crystal packing are from H⋯H (52.5%), N⋯H/H⋯N (19.2%), C⋯H/H⋯C (18.8%) and O⋯H/H⋯O (8.3%) interactions.
Keywords: crystal structure; hydrogen-bonding; C—H⋯π interactions; bicyclo [3.3.1]nonane ring system; Hirshfeld surface analysis.
CCDC reference: 2244417
1. Chemical context
Different C—C, C—N, and C—O bond-formation methods play important roles in various organic synthesis directions (Aliyeva et al., 2011; Zubkov et al., 2018; Viswanathan et al., 2019; Mamedov et al., 2022). Heterocyclic systems, especially those comprising the pyrano[3,2-c]pyridine scaffold, are present in many natural or synthetic products with a wide spectrum of biological properties, such as antitumor, antitubercular, cholinesterase inhibitor and anti-diabetic activities (Mamedov et al., 2019; Kumari et al., 2018). One of the most effective synthetic approaches to these polyfunctional heterocyclic systems is a Michael addition of active methylene compounds at the ylidene malononitrile functionality (Girgis et al., 2015). In a recent study (Mamedov et al., 2019), we found that the reaction of two moles of arylidene malononitriles with acetoacetanilide in the presence of piperazine hydrate leads to the formation of novel tricyclic pyrano[3,2-c]pyridine derivatives at room temperature (Fig. 1).
In this context and with respect to our on-going structural studies (Naghiyev et al., 2020, 2021, 2022; Khalilov et al., 2022), we report here the and Hirshfeld surface analysis of 2,5-diimino-8a-methyl-4,9-bis(4-methylphenyl)-7-oxo-6-phenyl-decahydro-2H-3,8-methanopyrano[3,2-c]pyridine-3,4a-dicarbonitrile N,N-dimethylformamide monosolvate, C32H29N5O2·C3H7NO.
2. Structural commentary
The molecular structure of the title compound is displayed in Fig. 2. The molecular conformation is stabilized by an intramolecular C—H⋯N hydrogen bond (Table 1) and consolidated by intermolecular C—H⋯O interactions involving the N,N-dimethylformamide solvent molecule (Fig. 2). As shown in Fig. 3, the bicyclo[3.3.1]nonane ring system (C2/N3/C4–C8/C1/C9) adopts a half-chair/twist-boat conformation; the puckering parameters (Cremer & Pople, 1975) are QT = 0.529 (2) Å, θ = 53.0 (2)°, φ = 160.1 (3)° for the (N3/C2/C1/C9/C5/C4) ring, and QT = 0.889 (2) Å, θ = 89.21 (13)°, φ = 289.11 (14)° for the (C1/C8/C7/C6/C5/C9) ring. The phenyl rings (C12–C17, C18–C23 and C26–C31) are in equatorial orientations with respect to the piperidine ring (C1/C2/N3/C4/C5/C9). The two oxane rings (O9/C9/C1/C8/C7/C10 and O9/C9/C5/C6/C7/C10) of the 2-oxabicyclo[2.2.2]octane ring system (C10/O9/C9/C1/C8/C7/C6/C5) exhibit a distorted boat conformation with puckering parameters QT = 0.799 (2) Å, θ = 91.88 (14)°, φ = 247.89 (15)° for the O9/C9/C1/C8C7/C10 ring, and QT = 0.826 (2) Å, θ = 96.04 (14)°, φ = 50.59 (15)° for the O9/C9/C5/C6/C7/C10 ring.
3. Supramolecular features and Hirshfeld surface analysis
In the crystal, intermolecular C—H⋯O and C—H⋯N hydrogen bonds (Table 1) link individual molecules, forming layers parallel to (100) (Fig. 4). These layers are connected by C—H⋯π interactions (Fig. 5). Interestingly, the imine C=N—H groups are not involved in hydrogen-bonding interactions.
A Hirshfeld surface analysis was performed to quantify the intermolecular interactions; the accompanying two-dimensional fingerprint plots were obtained using CrystalExplorer17 (Turner et al., 2017). The Hirshfeld surface mapped over dnorm using a standard surface resolution with a fixed colour scale of −0.1713 (red) to 1.4361 (blue) a.u. is shown in Fig. 6. The shorter and longer contacts are indicated as red and blue spots, respectively, on the Hirshfeld surfaces, and contacts with distances approximately equal to the sum of the van der Waals radii are represented as white spots. The most important red spots on the dnorm surface represent the aforementioned C—H⋯O and C—H⋯N interactions (Tables 1, 2).
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Fig. 7 depicts the two-dimensional fingerprint plots of (di, de) points from all the contacts contributing to the Hirshfeld surface analysis in normal mode for all atoms. The most important intermolecular interactions are H⋯H contacts, contributing 52.5% to the overall crystal packing. Other interactions and their respective contributions are N⋯H/H⋯N (19.2%), C⋯H/H⋯C (18.8%), O⋯H/H⋯O (8.3%), N⋯N (0.6%), C⋯N/N⋯C (0.3%), C⋯C (0.2%) and C⋯O/O⋯C (0.1%), respectively.
The Hirshfeld surface study verifies the significance of H-atom interactions in the packing formation. The contributions of H⋯H and N⋯H/H⋯N interactions imply that van der Waals interactions are important in the crystal packing (Hathwar et al., 2015).
4. Database survey
The five most similar compounds found in a search of the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016) for the bicyclo [3.3.1]nonane ring system are: 7-tert-butyl-N-methyl-2,4- diphenyl-3-azabicyclo[3.3.1]nonane (I) (Kumaran et al., 1999), N-acetyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonane (II) (Kumaran et al., 1999), N-methyl-2,4-bis(2- methylphenyl)-3-azabicyclo[3.3.1]nonan-9-ol (III) (Kumaran et al., 1999), 3-azabicyclo[3.3.1]nonane- 2,4-dione (form 2) (IV) (Hulme et al., 2006) and 2,4-bis(furan-2-yl)-1,5-dimethyl-3-azabicyclo [3.3.1]nonan-9-one (V) (Venkateswaramoorthi et al., 2013).
Compounds (I) and (III) crystallize in monoclinic space groups (P21/c, Z = 4, and P21/n, Z = 4, respectively), whereas (II) is orthorhombic (Pbca, Z = 8). In each of the three structures, the bicyclic ring system adopts a chair/chair conformation and the phenyl rings are in equatorial orientations with respect to the piperidine ring. In (II), apart from only weak intermolecular C—H⋯O-type interactions are involved in the packing.
The structure of (IV) has monoclinic symmetry (P21/c, Z = 8) and has two molecules in the A C22(8) chain motif (Bernstein et al., 1995) is formed via N—H⋯O hydrogen bonds.
In (V), which likewise is monoclinic (C2/c, Z = 8), the bicyclic ring system adopts a twin-chair conformation. The two methyl groups attached to the bicycle are in an equatorial orientation for both rings. In the crystal, very long N—H⋯O hydrogen bonds connect the molecules into a chain perpendicular to [010].
5. Synthesis and crystallization
The title compound was synthesized using a previously reported procedure (Mamedov et al., 2019). Colourless crystals were obtained upon recrystallization from an ethanol/water (3:1 v/v) solution.
6. Refinement
Crystal data, data collection and structure . All C-bound H atoms were placed at calculated positions and refined using a riding model, with C—H = 0.95–1.00 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C). The N-bound H atoms were located from difference-Fourier maps and refined with free atomic coordinates and Uiso = 1.2Ueq(N).
details are summarized in Table 3
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Supporting information
CCDC reference: 2244417
https://doi.org/10.1107/S2056989023001718/wm5672sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023001718/wm5672Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001718/wm5672Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2021); cell
CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).C32H27N5O2·C3H7NO | F(000) = 1240 |
Mr = 586.68 | Dx = 1.331 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 17.6747 (3) Å | Cell parameters from 19771 reflections |
b = 15.7656 (2) Å | θ = 3.8–79.0° |
c = 10.9086 (2) Å | µ = 0.70 mm−1 |
β = 105.666 (2)° | T = 100 K |
V = 2926.79 (9) Å3 | Prism, colourless |
Z = 4 | 0.14 × 0.11 × 0.08 mm |
XtaLAB Synergy, Dualflex, HyPix diffractometer | 5275 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.051 |
φ and ω scans | θmax = 79.5°, θmin = 3.8° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −22→21 |
Tmin = 0.900, Tmax = 0.936 | k = −20→19 |
31226 measured reflections | l = −12→13 |
6140 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.0745P)2 + 3.3477P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
6140 reflections | Δρmax = 0.34 e Å−3 |
408 parameters | Δρmin = −0.36 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. Owing to poor agreement between observed and calculated intensities, twenty-three outliers (2 5 1, 3 8 1, 1 8 9, 12 2 8, 1 8 1, 4 0 8, 2 1 1, 4 12 10, 4 2 7, 5 12 8, 1 1 7, 3 6 8, 6 3 9, 1 9 9, 12 11 1, 2 9 9, 1 9 7, 5 3 9, 5 14 7, 3 6 1, 0 1 7, 12 2 7, and 1 11 8) were omitted in the final cycles of refinement. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.84688 (12) | 0.49523 (12) | 0.84606 (19) | 0.0192 (4) | |
C2 | 0.90039 (12) | 0.46714 (13) | 0.76567 (19) | 0.0198 (4) | |
C4 | 0.81629 (12) | 0.33885 (13) | 0.70834 (19) | 0.0206 (4) | |
C5 | 0.77485 (12) | 0.35958 (13) | 0.81000 (19) | 0.0194 (4) | |
H5 | 0.766607 | 0.305061 | 0.851447 | 0.023* | |
C6 | 0.69240 (12) | 0.39782 (13) | 0.74590 (19) | 0.0203 (4) | |
H6 | 0.682604 | 0.393814 | 0.651413 | 0.024* | |
C7 | 0.69769 (12) | 0.49505 (13) | 0.78496 (19) | 0.0200 (4) | |
C8 | 0.77028 (12) | 0.53623 (13) | 0.75358 (19) | 0.0195 (4) | |
H8 | 0.769058 | 0.518255 | 0.665155 | 0.023* | |
C9 | 0.82223 (12) | 0.41853 (13) | 0.91434 (19) | 0.0198 (4) | |
C10 | 0.70680 (12) | 0.49526 (13) | 0.9264 (2) | 0.0207 (4) | |
C11 | 0.88965 (12) | 0.55627 (13) | 0.94255 (19) | 0.0201 (4) | |
C12 | 0.91367 (12) | 0.37153 (13) | 0.5957 (2) | 0.0214 (4) | |
C13 | 0.87775 (13) | 0.39897 (14) | 0.4729 (2) | 0.0261 (5) | |
H13 | 0.829930 | 0.429983 | 0.455287 | 0.031* | |
C14 | 0.91246 (15) | 0.38060 (16) | 0.3761 (2) | 0.0305 (5) | |
H14 | 0.888170 | 0.398723 | 0.291590 | 0.037* | |
C15 | 0.98255 (14) | 0.33583 (15) | 0.4026 (2) | 0.0283 (5) | |
H15 | 1.006297 | 0.323451 | 0.336214 | 0.034* | |
C16 | 1.01812 (13) | 0.30904 (14) | 0.5263 (2) | 0.0271 (5) | |
H16 | 1.066067 | 0.278253 | 0.544171 | 0.033* | |
C17 | 0.98380 (13) | 0.32713 (13) | 0.6236 (2) | 0.0241 (4) | |
H17 | 1.008099 | 0.309285 | 0.708266 | 0.029* | |
C18 | 0.62485 (12) | 0.35539 (13) | 0.7832 (2) | 0.0208 (4) | |
C19 | 0.63465 (13) | 0.31443 (13) | 0.9005 (2) | 0.0225 (4) | |
H19 | 0.685990 | 0.306811 | 0.955333 | 0.027* | |
C20 | 0.57009 (13) | 0.28484 (14) | 0.9374 (2) | 0.0241 (4) | |
H20 | 0.578280 | 0.256282 | 1.016577 | 0.029* | |
C21 | 0.49370 (13) | 0.29599 (14) | 0.8612 (2) | 0.0248 (5) | |
C22 | 0.48456 (13) | 0.33204 (14) | 0.7412 (2) | 0.0249 (5) | |
H22 | 0.433380 | 0.336973 | 0.684802 | 0.030* | |
C23 | 0.54892 (13) | 0.36093 (13) | 0.7026 (2) | 0.0231 (4) | |
H23 | 0.541005 | 0.384761 | 0.620081 | 0.028* | |
C24 | 0.42432 (13) | 0.27319 (15) | 0.9096 (2) | 0.0288 (5) | |
H24A | 0.408264 | 0.322797 | 0.950610 | 0.043* | |
H24B | 0.438846 | 0.226951 | 0.971608 | 0.043* | |
H24C | 0.380636 | 0.254957 | 0.838265 | 0.043* | |
C25 | 0.62564 (13) | 0.53826 (13) | 0.7117 (2) | 0.0231 (4) | |
C26 | 0.77331 (12) | 0.63271 (13) | 0.75573 (19) | 0.0213 (4) | |
C27 | 0.74616 (13) | 0.68268 (13) | 0.8408 (2) | 0.0229 (4) | |
H27 | 0.721083 | 0.656657 | 0.897947 | 0.028* | |
C28 | 0.75561 (13) | 0.77005 (14) | 0.8423 (2) | 0.0244 (4) | |
H28 | 0.736015 | 0.802987 | 0.899962 | 0.029* | |
C29 | 0.79307 (13) | 0.81081 (14) | 0.7616 (2) | 0.0242 (4) | |
C30 | 0.81945 (13) | 0.76077 (14) | 0.6766 (2) | 0.0251 (5) | |
H30 | 0.844772 | 0.786878 | 0.619812 | 0.030* | |
C31 | 0.80946 (13) | 0.67318 (14) | 0.6730 (2) | 0.0238 (4) | |
H31 | 0.827533 | 0.640525 | 0.613376 | 0.029* | |
C32 | 0.80575 (15) | 0.90535 (14) | 0.7689 (2) | 0.0301 (5) | |
H32A | 0.852432 | 0.918575 | 0.838280 | 0.045* | |
H32B | 0.759739 | 0.933163 | 0.784828 | 0.045* | |
H32C | 0.813314 | 0.925827 | 0.688169 | 0.045* | |
C33 | 0.89004 (12) | 0.37404 (13) | 1.0063 (2) | 0.0218 (4) | |
H33A | 0.919202 | 0.414849 | 1.069304 | 0.033* | |
H33B | 0.925089 | 0.349923 | 0.959485 | 0.033* | |
H33C | 0.869776 | 0.328506 | 1.049816 | 0.033* | |
C34 | 0.63579 (14) | 0.47173 (15) | 0.3770 (2) | 0.0275 (5) | |
H34 | 0.593630 | 0.505419 | 0.388302 | 0.033* | |
C35 | 0.68357 (15) | 0.37063 (15) | 0.2489 (2) | 0.0300 (5) | |
H35A | 0.709455 | 0.394672 | 0.187861 | 0.045* | |
H35B | 0.658547 | 0.316752 | 0.215915 | 0.045* | |
H35C | 0.722664 | 0.360780 | 0.330382 | 0.045* | |
C36 | 0.54932 (14) | 0.43254 (18) | 0.1702 (2) | 0.0338 (5) | |
H36A | 0.521478 | 0.378714 | 0.169526 | 0.051* | |
H36B | 0.558662 | 0.441861 | 0.086657 | 0.051* | |
H36C | 0.517414 | 0.479056 | 0.188991 | 0.051* | |
N2 | 0.95780 (11) | 0.51308 (12) | 0.75995 (18) | 0.0242 (4) | |
H2N | 0.9840 (16) | 0.4923 (18) | 0.702 (3) | 0.029* | |
N3 | 0.87658 (10) | 0.39156 (11) | 0.69547 (16) | 0.0205 (4) | |
N10 | 0.66000 (11) | 0.52902 (12) | 0.98087 (19) | 0.0252 (4) | |
H10N | 0.6751 (16) | 0.5206 (18) | 1.071 (3) | 0.030* | |
N11 | 0.92084 (11) | 0.60155 (12) | 1.02287 (17) | 0.0250 (4) | |
N25 | 0.57038 (11) | 0.56806 (13) | 0.64654 (19) | 0.0298 (4) | |
N34 | 0.62423 (11) | 0.42955 (12) | 0.26736 (18) | 0.0265 (4) | |
O4 | 0.79621 (9) | 0.27759 (10) | 0.63952 (15) | 0.0270 (4) | |
O9 | 0.77226 (8) | 0.45054 (9) | 0.99082 (13) | 0.0202 (3) | |
O34 | 0.69653 (10) | 0.47051 (11) | 0.46440 (15) | 0.0332 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0237 (10) | 0.0151 (9) | 0.0192 (9) | −0.0017 (7) | 0.0064 (8) | −0.0003 (7) |
C2 | 0.0234 (10) | 0.0172 (9) | 0.0190 (9) | 0.0005 (8) | 0.0063 (8) | 0.0001 (8) |
C4 | 0.0235 (10) | 0.0171 (9) | 0.0218 (10) | 0.0008 (8) | 0.0069 (8) | 0.0007 (8) |
C5 | 0.0240 (10) | 0.0146 (9) | 0.0209 (10) | −0.0016 (7) | 0.0080 (8) | −0.0012 (7) |
C6 | 0.0245 (10) | 0.0162 (9) | 0.0198 (10) | 0.0002 (8) | 0.0052 (8) | −0.0017 (7) |
C7 | 0.0219 (10) | 0.0168 (9) | 0.0210 (10) | 0.0003 (8) | 0.0052 (8) | 0.0000 (8) |
C8 | 0.0248 (10) | 0.0178 (9) | 0.0166 (9) | −0.0004 (8) | 0.0064 (8) | −0.0003 (7) |
C9 | 0.0231 (10) | 0.0172 (9) | 0.0207 (10) | 0.0000 (8) | 0.0086 (8) | −0.0010 (8) |
C10 | 0.0239 (10) | 0.0148 (9) | 0.0235 (10) | −0.0018 (7) | 0.0066 (8) | −0.0002 (8) |
C11 | 0.0242 (10) | 0.0164 (9) | 0.0209 (10) | 0.0007 (8) | 0.0080 (8) | 0.0000 (8) |
C12 | 0.0273 (10) | 0.0176 (9) | 0.0210 (10) | −0.0034 (8) | 0.0092 (8) | −0.0031 (8) |
C13 | 0.0284 (11) | 0.0244 (11) | 0.0260 (11) | 0.0021 (9) | 0.0081 (9) | 0.0000 (9) |
C14 | 0.0384 (13) | 0.0314 (12) | 0.0233 (11) | −0.0003 (10) | 0.0110 (9) | 0.0015 (9) |
C15 | 0.0363 (12) | 0.0256 (11) | 0.0282 (11) | −0.0051 (9) | 0.0179 (9) | −0.0069 (9) |
C16 | 0.0278 (11) | 0.0213 (10) | 0.0346 (12) | −0.0010 (9) | 0.0126 (9) | −0.0039 (9) |
C17 | 0.0282 (11) | 0.0184 (10) | 0.0262 (11) | −0.0007 (8) | 0.0082 (8) | −0.0009 (8) |
C18 | 0.0242 (10) | 0.0151 (9) | 0.0237 (10) | −0.0001 (8) | 0.0078 (8) | −0.0037 (8) |
C19 | 0.0243 (10) | 0.0196 (10) | 0.0224 (10) | −0.0005 (8) | 0.0046 (8) | −0.0012 (8) |
C20 | 0.0303 (11) | 0.0212 (10) | 0.0216 (10) | −0.0029 (8) | 0.0083 (9) | −0.0013 (8) |
C21 | 0.0282 (11) | 0.0191 (10) | 0.0285 (11) | −0.0030 (8) | 0.0100 (9) | −0.0049 (8) |
C22 | 0.0238 (10) | 0.0216 (10) | 0.0274 (11) | −0.0006 (8) | 0.0035 (8) | −0.0026 (8) |
C23 | 0.0298 (11) | 0.0178 (10) | 0.0213 (10) | −0.0009 (8) | 0.0062 (8) | −0.0003 (8) |
C24 | 0.0274 (11) | 0.0276 (12) | 0.0328 (12) | −0.0032 (9) | 0.0103 (9) | −0.0026 (9) |
C25 | 0.0265 (11) | 0.0188 (10) | 0.0254 (11) | −0.0018 (8) | 0.0093 (9) | −0.0021 (8) |
C26 | 0.0241 (10) | 0.0181 (10) | 0.0203 (10) | 0.0002 (8) | 0.0037 (8) | 0.0018 (8) |
C27 | 0.0287 (11) | 0.0184 (10) | 0.0228 (10) | 0.0001 (8) | 0.0088 (8) | 0.0012 (8) |
C28 | 0.0307 (11) | 0.0194 (10) | 0.0223 (10) | 0.0020 (8) | 0.0059 (9) | −0.0016 (8) |
C29 | 0.0282 (11) | 0.0189 (10) | 0.0224 (10) | −0.0004 (8) | 0.0018 (8) | 0.0019 (8) |
C30 | 0.0324 (11) | 0.0199 (10) | 0.0230 (10) | −0.0028 (9) | 0.0073 (9) | 0.0034 (8) |
C31 | 0.0300 (11) | 0.0210 (10) | 0.0213 (10) | 0.0004 (8) | 0.0084 (8) | 0.0003 (8) |
C32 | 0.0392 (13) | 0.0185 (10) | 0.0317 (12) | −0.0009 (9) | 0.0076 (10) | 0.0021 (9) |
C33 | 0.0259 (10) | 0.0173 (9) | 0.0220 (10) | −0.0006 (8) | 0.0060 (8) | 0.0014 (8) |
C34 | 0.0314 (11) | 0.0279 (11) | 0.0243 (11) | 0.0010 (9) | 0.0094 (9) | −0.0010 (9) |
C35 | 0.0376 (13) | 0.0254 (11) | 0.0277 (11) | 0.0027 (9) | 0.0100 (10) | −0.0009 (9) |
C36 | 0.0295 (12) | 0.0434 (14) | 0.0277 (12) | 0.0001 (10) | 0.0063 (9) | −0.0046 (10) |
N2 | 0.0280 (9) | 0.0221 (9) | 0.0245 (9) | −0.0027 (7) | 0.0105 (8) | −0.0021 (7) |
N3 | 0.0255 (9) | 0.0163 (8) | 0.0217 (8) | −0.0020 (7) | 0.0098 (7) | −0.0027 (7) |
N10 | 0.0311 (10) | 0.0216 (9) | 0.0260 (10) | −0.0001 (7) | 0.0131 (8) | 0.0001 (7) |
N11 | 0.0283 (9) | 0.0212 (9) | 0.0255 (9) | −0.0004 (7) | 0.0073 (7) | −0.0010 (7) |
N25 | 0.0291 (10) | 0.0244 (10) | 0.0346 (11) | 0.0011 (8) | 0.0061 (8) | 0.0030 (8) |
N34 | 0.0288 (10) | 0.0263 (10) | 0.0241 (9) | 0.0010 (8) | 0.0064 (8) | −0.0018 (7) |
O4 | 0.0322 (8) | 0.0205 (7) | 0.0307 (8) | −0.0034 (6) | 0.0126 (7) | −0.0073 (6) |
O9 | 0.0241 (7) | 0.0187 (7) | 0.0191 (7) | 0.0014 (5) | 0.0081 (6) | 0.0003 (5) |
O34 | 0.0358 (9) | 0.0365 (9) | 0.0253 (8) | 0.0032 (7) | 0.0049 (7) | −0.0042 (7) |
C1—C11 | 1.475 (3) | C20—C21 | 1.392 (3) |
C1—C2 | 1.519 (3) | C20—H20 | 0.9500 |
C1—C9 | 1.543 (3) | C21—C22 | 1.396 (3) |
C1—C8 | 1.591 (3) | C21—C24 | 1.504 (3) |
C2—N2 | 1.262 (3) | C22—C23 | 1.392 (3) |
C2—N3 | 1.418 (3) | C22—H22 | 0.9500 |
C4—O4 | 1.216 (3) | C23—H23 | 0.9500 |
C4—N3 | 1.388 (3) | C24—H24A | 0.9800 |
C4—C5 | 1.520 (3) | C24—H24B | 0.9800 |
C5—C9 | 1.532 (3) | C24—H24C | 0.9800 |
C5—C6 | 1.557 (3) | C25—N25 | 1.143 (3) |
C5—H5 | 1.0000 | C26—C31 | 1.393 (3) |
C6—C18 | 1.517 (3) | C26—C27 | 1.397 (3) |
C6—C7 | 1.587 (3) | C27—C28 | 1.387 (3) |
C6—H6 | 1.0000 | C27—H27 | 0.9500 |
C7—C25 | 1.475 (3) | C28—C29 | 1.393 (3) |
C7—C10 | 1.507 (3) | C28—H28 | 0.9500 |
C7—C8 | 1.556 (3) | C29—C30 | 1.391 (3) |
C8—C26 | 1.522 (3) | C29—C32 | 1.506 (3) |
C8—H8 | 1.0000 | C30—C31 | 1.391 (3) |
C9—O9 | 1.459 (2) | C30—H30 | 0.9500 |
C9—C33 | 1.512 (3) | C31—H31 | 0.9500 |
C10—N10 | 1.259 (3) | C32—H32A | 0.9800 |
C10—O9 | 1.375 (2) | C32—H32B | 0.9800 |
C11—N11 | 1.149 (3) | C32—H32C | 0.9800 |
C12—C17 | 1.384 (3) | C33—H33A | 0.9800 |
C12—C13 | 1.388 (3) | C33—H33B | 0.9800 |
C12—N3 | 1.449 (3) | C33—H33C | 0.9800 |
C13—C14 | 1.387 (3) | C34—O34 | 1.229 (3) |
C13—H13 | 0.9500 | C34—N34 | 1.335 (3) |
C14—C15 | 1.387 (3) | C34—H34 | 0.9500 |
C14—H14 | 0.9500 | C35—N34 | 1.455 (3) |
C15—C16 | 1.392 (3) | C35—H35A | 0.9800 |
C15—H15 | 0.9500 | C35—H35B | 0.9800 |
C16—C17 | 1.387 (3) | C35—H35C | 0.9800 |
C16—H16 | 0.9500 | C36—N34 | 1.456 (3) |
C17—H17 | 0.9500 | C36—H36A | 0.9800 |
C18—C23 | 1.395 (3) | C36—H36B | 0.9800 |
C18—C19 | 1.401 (3) | C36—H36C | 0.9800 |
C19—C20 | 1.389 (3) | N2—H2N | 0.94 (3) |
C19—H19 | 0.9500 | N10—H10N | 0.95 (3) |
C11—C1—C2 | 108.85 (17) | C21—C20—H20 | 119.2 |
C11—C1—C9 | 108.90 (17) | C20—C21—C22 | 117.3 (2) |
C2—C1—C9 | 110.55 (16) | C20—C21—C24 | 120.8 (2) |
C11—C1—C8 | 111.83 (16) | C22—C21—C24 | 121.8 (2) |
C2—C1—C8 | 107.95 (16) | C23—C22—C21 | 121.3 (2) |
C9—C1—C8 | 108.76 (16) | C23—C22—H22 | 119.3 |
N2—C2—N3 | 125.53 (19) | C21—C22—H22 | 119.3 |
N2—C2—C1 | 119.71 (19) | C22—C23—C18 | 120.9 (2) |
N3—C2—C1 | 114.63 (17) | C22—C23—H23 | 119.5 |
O4—C4—N3 | 121.14 (19) | C18—C23—H23 | 119.5 |
O4—C4—C5 | 120.22 (18) | C21—C24—H24A | 109.5 |
N3—C4—C5 | 118.64 (17) | C21—C24—H24B | 109.5 |
C4—C5—C9 | 113.46 (17) | H24A—C24—H24B | 109.5 |
C4—C5—C6 | 109.41 (16) | C21—C24—H24C | 109.5 |
C9—C5—C6 | 110.87 (16) | H24A—C24—H24C | 109.5 |
C4—C5—H5 | 107.6 | H24B—C24—H24C | 109.5 |
C9—C5—H5 | 107.6 | N25—C25—C7 | 174.4 (2) |
C6—C5—H5 | 107.6 | C31—C26—C27 | 118.15 (19) |
C18—C6—C5 | 114.69 (17) | C31—C26—C8 | 117.91 (19) |
C18—C6—C7 | 110.33 (16) | C27—C26—C8 | 123.83 (19) |
C5—C6—C7 | 105.86 (16) | C28—C27—C26 | 120.4 (2) |
C18—C6—H6 | 108.6 | C28—C27—H27 | 119.8 |
C5—C6—H6 | 108.6 | C26—C27—H27 | 119.8 |
C7—C6—H6 | 108.6 | C27—C28—C29 | 121.8 (2) |
C25—C7—C10 | 113.04 (18) | C27—C28—H28 | 119.1 |
C25—C7—C8 | 109.31 (17) | C29—C28—H28 | 119.1 |
C10—C7—C8 | 110.95 (17) | C30—C29—C28 | 117.5 (2) |
C25—C7—C6 | 108.74 (16) | C30—C29—C32 | 121.6 (2) |
C10—C7—C6 | 105.03 (16) | C28—C29—C32 | 120.8 (2) |
C8—C7—C6 | 109.64 (16) | C29—C30—C31 | 121.2 (2) |
C26—C8—C7 | 116.18 (17) | C29—C30—H30 | 119.4 |
C26—C8—C1 | 112.08 (16) | C31—C30—H30 | 119.4 |
C7—C8—C1 | 107.58 (16) | C30—C31—C26 | 120.9 (2) |
C26—C8—H8 | 106.8 | C30—C31—H31 | 119.6 |
C7—C8—H8 | 106.8 | C26—C31—H31 | 119.6 |
C1—C8—H8 | 106.8 | C29—C32—H32A | 109.5 |
O9—C9—C33 | 105.95 (16) | C29—C32—H32B | 109.5 |
O9—C9—C5 | 109.93 (16) | H32A—C32—H32B | 109.5 |
C33—C9—C5 | 112.84 (17) | C29—C32—H32C | 109.5 |
O9—C9—C1 | 107.35 (16) | H32A—C32—H32C | 109.5 |
C33—C9—C1 | 114.04 (17) | H32B—C32—H32C | 109.5 |
C5—C9—C1 | 106.61 (16) | C9—C33—H33A | 109.5 |
N10—C10—O9 | 123.02 (19) | C9—C33—H33B | 109.5 |
N10—C10—C7 | 125.6 (2) | H33A—C33—H33B | 109.5 |
O9—C10—C7 | 111.38 (17) | C9—C33—H33C | 109.5 |
N11—C11—C1 | 175.8 (2) | H33A—C33—H33C | 109.5 |
C17—C12—C13 | 121.3 (2) | H33B—C33—H33C | 109.5 |
C17—C12—N3 | 120.32 (19) | O34—C34—N34 | 125.3 (2) |
C13—C12—N3 | 118.38 (19) | O34—C34—H34 | 117.3 |
C14—C13—C12 | 119.2 (2) | N34—C34—H34 | 117.3 |
C14—C13—H13 | 120.4 | N34—C35—H35A | 109.5 |
C12—C13—H13 | 120.4 | N34—C35—H35B | 109.5 |
C15—C14—C13 | 120.1 (2) | H35A—C35—H35B | 109.5 |
C15—C14—H14 | 119.9 | N34—C35—H35C | 109.5 |
C13—C14—H14 | 119.9 | H35A—C35—H35C | 109.5 |
C14—C15—C16 | 120.0 (2) | H35B—C35—H35C | 109.5 |
C14—C15—H15 | 120.0 | N34—C36—H36A | 109.5 |
C16—C15—H15 | 120.0 | N34—C36—H36B | 109.5 |
C17—C16—C15 | 120.2 (2) | H36A—C36—H36B | 109.5 |
C17—C16—H16 | 119.9 | N34—C36—H36C | 109.5 |
C15—C16—H16 | 119.9 | H36A—C36—H36C | 109.5 |
C12—C17—C16 | 119.1 (2) | H36B—C36—H36C | 109.5 |
C12—C17—H17 | 120.4 | C2—N2—H2N | 112.5 (17) |
C16—C17—H17 | 120.4 | C4—N3—C2 | 124.93 (17) |
C23—C18—C19 | 117.73 (19) | C4—N3—C12 | 117.45 (17) |
C23—C18—C6 | 119.75 (19) | C2—N3—C12 | 117.42 (17) |
C19—C18—C6 | 122.41 (18) | C10—N10—H10N | 112.8 (17) |
C20—C19—C18 | 120.7 (2) | C34—N34—C35 | 120.03 (19) |
C20—C19—H19 | 119.7 | C34—N34—C36 | 121.7 (2) |
C18—C19—H19 | 119.7 | C35—N34—C36 | 117.86 (19) |
C19—C20—C21 | 121.7 (2) | C10—O9—C9 | 116.16 (15) |
C19—C20—H20 | 119.2 | ||
C11—C1—C2—N2 | −21.8 (3) | N3—C12—C13—C14 | 179.8 (2) |
C9—C1—C2—N2 | −141.3 (2) | C12—C13—C14—C15 | −0.5 (3) |
C8—C1—C2—N2 | 99.8 (2) | C13—C14—C15—C16 | 0.2 (4) |
C11—C1—C2—N3 | 162.27 (17) | C14—C15—C16—C17 | −0.2 (3) |
C9—C1—C2—N3 | 42.7 (2) | C13—C12—C17—C16 | −0.7 (3) |
C8—C1—C2—N3 | −76.1 (2) | N3—C12—C17—C16 | −179.82 (19) |
O4—C4—C5—C9 | 161.19 (19) | C15—C16—C17—C12 | 0.4 (3) |
N3—C4—C5—C9 | −19.4 (3) | C5—C6—C18—C23 | −156.70 (18) |
O4—C4—C5—C6 | −74.4 (2) | C7—C6—C18—C23 | 83.9 (2) |
N3—C4—C5—C6 | 105.0 (2) | C5—C6—C18—C19 | 27.2 (3) |
C4—C5—C6—C18 | 128.31 (18) | C7—C6—C18—C19 | −92.2 (2) |
C9—C5—C6—C18 | −105.81 (19) | C23—C18—C19—C20 | −3.6 (3) |
C4—C5—C6—C7 | −109.82 (18) | C6—C18—C19—C20 | 172.57 (19) |
C9—C5—C6—C7 | 16.1 (2) | C18—C19—C20—C21 | −1.2 (3) |
C18—C6—C7—C25 | −64.0 (2) | C19—C20—C21—C22 | 5.1 (3) |
C5—C6—C7—C25 | 171.40 (16) | C19—C20—C21—C24 | −172.4 (2) |
C18—C6—C7—C10 | 57.3 (2) | C20—C21—C22—C23 | −4.2 (3) |
C5—C6—C7—C10 | −67.34 (19) | C24—C21—C22—C23 | 173.3 (2) |
C18—C6—C7—C8 | 176.56 (16) | C21—C22—C23—C18 | −0.5 (3) |
C5—C6—C7—C8 | 51.9 (2) | C19—C18—C23—C22 | 4.4 (3) |
C25—C7—C8—C26 | 47.0 (2) | C6—C18—C23—C22 | −171.82 (19) |
C10—C7—C8—C26 | −78.3 (2) | C7—C8—C26—C31 | −148.55 (19) |
C6—C7—C8—C26 | 166.10 (16) | C1—C8—C26—C31 | 87.2 (2) |
C25—C7—C8—C1 | 173.51 (16) | C7—C8—C26—C27 | 35.4 (3) |
C10—C7—C8—C1 | 48.2 (2) | C1—C8—C26—C27 | −88.9 (2) |
C6—C7—C8—C1 | −67.4 (2) | C31—C26—C27—C28 | −0.3 (3) |
C11—C1—C8—C26 | 19.3 (2) | C8—C26—C27—C28 | 175.78 (19) |
C2—C1—C8—C26 | −100.43 (19) | C26—C27—C28—C29 | −1.0 (3) |
C9—C1—C8—C26 | 139.59 (17) | C27—C28—C29—C30 | 1.4 (3) |
C11—C1—C8—C7 | −109.61 (19) | C27—C28—C29—C32 | −177.4 (2) |
C2—C1—C8—C7 | 130.67 (17) | C28—C29—C30—C31 | −0.6 (3) |
C9—C1—C8—C7 | 10.7 (2) | C32—C29—C30—C31 | 178.2 (2) |
C4—C5—C9—O9 | 167.19 (16) | C29—C30—C31—C26 | −0.7 (3) |
C6—C5—C9—O9 | 43.6 (2) | C27—C26—C31—C30 | 1.1 (3) |
C4—C5—C9—C33 | −74.8 (2) | C8—C26—C31—C30 | −175.21 (19) |
C6—C5—C9—C33 | 161.62 (17) | O4—C4—N3—C2 | 175.69 (19) |
C4—C5—C9—C1 | 51.1 (2) | C5—C4—N3—C2 | −3.7 (3) |
C6—C5—C9—C1 | −72.5 (2) | O4—C4—N3—C12 | 1.0 (3) |
C11—C1—C9—O9 | 59.6 (2) | C5—C4—N3—C12 | −178.45 (17) |
C2—C1—C9—O9 | 179.10 (15) | N2—C2—N3—C4 | 175.9 (2) |
C8—C1—C9—O9 | −62.54 (19) | C1—C2—N3—C4 | −8.5 (3) |
C11—C1—C9—C33 | −57.5 (2) | N2—C2—N3—C12 | −9.4 (3) |
C2—C1—C9—C33 | 62.1 (2) | C1—C2—N3—C12 | 166.25 (17) |
C8—C1—C9—C33 | −179.57 (16) | C17—C12—N3—C4 | −98.1 (2) |
C11—C1—C9—C5 | 177.32 (16) | C13—C12—N3—C4 | 82.8 (2) |
C2—C1—C9—C5 | −63.1 (2) | C17—C12—N3—C2 | 86.7 (2) |
C8—C1—C9—C5 | 55.2 (2) | C13—C12—N3—C2 | −92.4 (2) |
C25—C7—C10—N10 | −1.0 (3) | O34—C34—N34—C35 | 5.8 (4) |
C8—C7—C10—N10 | 122.2 (2) | O34—C34—N34—C36 | 178.1 (2) |
C6—C7—C10—N10 | −119.4 (2) | N10—C10—O9—C9 | −177.47 (19) |
C25—C7—C10—O9 | 176.72 (16) | C7—C10—O9—C9 | 4.7 (2) |
C8—C7—C10—O9 | −60.1 (2) | C33—C9—O9—C10 | 178.80 (16) |
C6—C7—C10—O9 | 58.3 (2) | C5—C9—O9—C10 | −59.0 (2) |
C17—C12—C13—C14 | 0.8 (3) | C1—C9—O9—C10 | 56.6 (2) |
Cg7 is the centroid of the C26–C31 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O34 | 1.00 | 2.44 | 3.297 (3) | 143 |
C8—H8···O34 | 1.00 | 2.34 | 3.241 (3) | 149 |
C13—H13···O34 | 0.95 | 2.47 | 3.373 (3) | 159 |
C27—H27···N10 | 0.95 | 2.56 | 3.432 (3) | 152 |
C30—H30···N11i | 0.95 | 2.61 | 3.515 (3) | 160 |
C33—H33C···O4ii | 0.98 | 2.48 | 3.447 (3) | 170 |
C35—H35C···O34 | 0.98 | 2.39 | 2.787 (3) | 104 |
C24—H24C···Cg7iii | 0.98 | 2.84 | 3.715 (2) | 148 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2. |
Atoms | Distance | Symmetry code |
O4···H33C | 2.48 | x, 1/2 - y, -1/2 + z |
H10N···H35A | 2.35 | x, y, 1 + z |
H10N···H32B | 2.52 | x, 3/2 - y, 1/2 + z |
H33A···N2 | 2.70 | 2 - x, 1 - y, 2 - z |
H15···N2 | 2.92 | 2 - x, 1 - y, 1 - z |
H24A···N10 | 2.82 | 1 - x, 1 - y, 2 - z |
C29···H16 | 2.85 | 2 - x, 1/2 + y, 3/2 - z |
C28···H24C | 2.68 | 1 - x, 1/2 + y, 3/2 - z |
N25···H36C | 2.77 | 1 - x, 1 - y, 1 - z |
H13···H35C | 2.29 | x, y, z |
C18···H35B | 2.91 | x, 1/2 - y, 1/2 + z |
H32B···C34 | 3.04 | x, 3/2 - y, 1/2 + z |
Acknowledgements
Author contributions are as follows. Conceptualization, ANK and IGM; methodology, ANK, FNN and IGM; investigation, ANK, MA and APN; writing (original draft), MA and ANK; writing (review and editing of the manuscript), MA and ANK; visualization, MA, ANK and IGM; funding acquisition, VNK, AB and ANK; resources, AB, VNK and APN; supervision, ANK and MA.
Funding information
This paper was supported by Baku State University and the Ministry of Science and Higher Education of the Russian Federation [award No. 075–03–2020-223 (FSSF-2020–0017)].
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