research communications
E)-2-{[(E)-2-hydroxy-5-methylbenzylidene]hydrazinylidene}-1,2-diphenylethan-1-one
and molecular docking study of (aSamsun University, Faculty of Engineering, Department of Fundamental Sciences, 55420, Samsun, Turkey, bOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, Turkey, cOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey, dSamsun University, Faculty of Engineering, Biomedical Engineering, 55420, Samsun, Turkey, eIbb University, Science College, Department of Physics, Ibb, Yemen, and fAljanad University for Science & Technology, Engineering College, Taiz, Yemen
*Correspondence e-mail: sevgi.kansiz@samsun.edu.tr, samirbas@gmail.com
The title compound, C22H18N2O2, is a Schiff base that exists in the phenol–imine tautomeric form and adopts an E configuration with respect to the C=N bond. The molecular structure is stabilized by an O—H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules to form inversion dimers. Weak π–π stacking interactions along the a-axis direction provide additional stabilization of the The molecule is non-planar, the aromatic ring of the benzaldehyde residue being nearly perpendicular to the phenyl and 4-methylphenol rings with dihedral angles of 88.78 (13) and 82.26 (14)°, respectively. A molecular docking study between the title molecule and the COVID-19 main protease (PDB ID: 6LU7) was performed, showing that it is a potential agent because of its affinity and ability to adhere to the active sites of the protein.
Keywords: crystal structure; Schiff base; diphenylethan; molecular docking; COVID-19 main protease.
CCDC reference: 2085577
1. Chemical context
), biologically active materials (Al Zoubi, 2013) and thermostable systems (Destri et al., 1998). The optical and semiconducting phenomena of the azomethine linkage group have been also widely investigated as a result of their photo-efficiency, with wavelengths depending on the chemical architecture of the Schiff-base molecules (Iwan & Sek, 2008). have significant importance in the development of metal complexes, because Schiff base ligands are potentially capable of forming stable complexes by coordination of metal ions via their oxygen and nitrogen donors (Ebrahimipour et al., 2012). Hydrazine, hydrazone and hydrazide derivatives are relatively scarce in nature and have been isolated from plants, marine organisms and microorganisms. These compounds exhibit remarkable structural diversity and relevant biological activities (Le Goff & Ouazzani, 2014). Salicylaldehyde complexes with transition metals have worked as antimalarial and antileukemic agents (Scovill et al., 1982). In this study, a new Schiff base with potential biological character, (E)-2-{[(E)-2-hydroxy-5-methylbenzylidene]hydrazineylidene}-1,2-diphenylethan-1-one, was obtained in crystalline form from the reaction of 2-hydroxy-5-methylbenzaldehyde with (E)-2-hydrazineylidene-1,2-diphenylethan-1-one. We report here the synthesis, crystal and molecular structure of the title compound. We have also performed a molecular docking study to determine possible intermolecular interactions between the COVID-19 main protease (PDB ID: 6LU7) and the title compound.
have wide applications interests as corrosion inhibitors (Antonijevic & Petrovic, 20082. Structural commentary
The ), which crystallizes in the phenol–imine tautomeric form with an E configuration for the imine functionality. The hydroxy H atom is involved in a strong intramolecular O—H⋯N hydrogen bond, forming an S(6) ring motif, which stabilizes the molecular structure. The dibenzylidene hydrazine unit is approximately planar with the dihedral angle formed by the two terminal phenyl rings of 7.62 (15)°. On the other hand, the molecule is non-planar, because the C1–C6 ring is nearly perpendicular to the C9–C14 and C16–C21 rings with dihedral angles of 88.78 (13) and 82.26 (14)°, respectively. The C17—O2, C15—N2 and C15—C16 bond lengths in the molecule are 1.359 (5), 1.287 (5), and 1.452 (5) Å, respectively. These results suggest single-bond character for C17—O2 and C15—C16 and double-bond character for the C15—N2 bond as expected for a phenol–imine structure (Kaştaş et al., 2020). The bond lengths and angles in the title molecule agree reasonably well with those found in closely related structures (Bouchama et al., 2015; Wieland et al., 2011). Based on the parameters, the tautomeric form of the compound is the phenol–imine form in which the tautomeric proton (H2) is located on the phenolic oxygen atom (O2). The distance of 2.650 (5) Å between the nitrogen and the oxygen atoms show that the molecule has a strong O—H⋯N intramolecular hydrogen bond, forming an S(6) ring motif.
of the title structure contains one molecule (Fig. 13. Supramolecular features
In the crystal, molecules are linked by pairs of C3—H3⋯O2 hydrogen bonds, forming inversion dimers with an R22(11) ring motif (Table 1 and Fig. 2). There are also weak π–π interactions [Cg2⋯Cg3(−x, −y, −z) = 3.909 (2) Å; Cg2 and Cg3 are the centroids of the C9–C14 and C16–C21 rings, respectively] that stabilize the forming a three-dimensional network.
4. Database survey
A search of the Cambridge Structural Database (CSD, version 5.42, update November 2020; Groom et al., 2016) for the (benzylidenehydrazono)-1,2-diphenylethanone skeleton revealed 14 similar compounds. In MOZZEH01 (Marcel et al., 2011), the C=N [1.291 (2) Å], N—N [1.414 (2) Å] and C=O bond lengths [1.235 (1) Å] are within the ranges observed for the title compound. The C7—C8 bond distance of 1.523 (2) Å corresponding to the value expected for a Csp2—Csp2 single bond, is slightly longer than observed for the title compound [1.472 (5) Å]. This bond length is shorter than in NOTZIH [1.528 (3) Å; Bouchama et al., 2015]. In HULFAX (Elmacı et al., 2015), the C15—N2 bond length [1.276 (4) Å] is typical of for an azomethine C=N bond and shorter than in the title compound [1.287 (5) Å]. In MOZZEH (Patra et al., 2009) and MUBTUZ (Patra & Ng, 2009), the dimethylene hydrazine (—C=N—N=C—) units are approximately planar, the torsion angles around the N—N bond being 177.82 (12) and 162.2 (6)°, respectively. Although these values are comparable to the title compound, they are slightly smaller than 178.3 (3)°. In LOTKEN (Yahyaoui et al., 2019), N—N (hydrazone) distances are within the range of typical single bond [1.398 (6)–1.4077 (16) Å and the C=N bonds in the hydrazone units are between 1.2893 (19) and 1.3014 (18) Å]. The torsion angles involving the —N=C— vary between −171.02 and −179.90°. All these values are similar to those observed in the title compound.
5. Molecular docking study
Molecular docking is a crucial method for investigating the interaction between small molecules and macromolecules. Intermolecular contacts that occur between a ligand and a protein are evaluated by molecular docking. In summary, this method is one of the major approaches to estimate the binding area where the ligand connects with the protein. In this study, AutoDockVina (Trott & Olson, 2010) was utilized for predicting binding sites between the title molecule and 6LU7. 6LU7 is a main protease of COVID-19, and can be efficient for drug design to treat ailments (Jin et al., 2020). The three-dimensional structure of 6LU7 was received from the Protein Data Bank (PDB). Before the computation, the protein must be prepared for efficient insertion. Therefore, all water molecules and ligands were removed from protein active sites. LYS102, VAL104, GLN110, THR111, ASN151, ASP153 and SER158 were defined as active areas. According to these active sites, grid box dimensions were determined to be 100 × 100 × 95 Å. In addition, `x, y, z' centers were adjusted to be −20.378, 27.848, 69.124, respectively, and then the 6LU7 protein was saved in PDBQT format for calculations. In the next step of the experiment, rotatable angles for coupling structures were identified and recorded in PDBQT format. Discovery Studio Visualizer (Biovia, 2017) was used for observations and preparations. All docking calculations were computed with AutoDockVina. Twenty variable adherences were decided by AutoDockVina for the ligands connected to the receptor of the protein. The best affinity energy was observed in the first calculation, of −7.2 kcal mol−1. The bonding type of interaction is demonstrated in Fig. 3. The 2D and 3D visuals of the intermolecular interactions for the best binding pose of the title compound docked into macromolecule 6LU7 can be seen in Fig. 4. In addition, the docking conformation is shown in Fig. 5. As a consequence, the title compound could be a potential molecule for drug design to treat severe acute respiratory syndrome resulting from the novel corona virus SARS CoV2 because of its affinity and ability suitable to adhere to active sites of the protein.
6. Synthesis and crystallization
(E)-2-{[(E)-2-Hydroxy-5-methylbenzylidene]hydrazineylidene}-1,2-diphenylethan-1-one was prepared by refluxing a mixture of a solution containing 2-hydroxy-5-methylbenzaldehyde (0.02 mmol) in ethanol (20 mL) and a solution containing (E)-2-hydrazineylidene-1,2-diphenylethan-1-one (0.02 mmol) in ethanol (20 mL). The reaction mixture was stirred for 5 h under reflux. The obtained crystalline material was washed with ethanol and dried at room temperature. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution.
7. Refinement
Crystal data, data collection and structure . The O-bound H atom was located in a difference-Fourier map and refined with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O). The C-bound H atoms were positioned geometrically and refined using a riding model with C—H = 0.93 and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms.
details are summarized in Table 2Supporting information
CCDC reference: 2085577
https://doi.org/10.1107/S2056989021005442/yk2152sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021005442/yk2152Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989021005442/yk2152Isup3.cml
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2018/3 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).C22H18N2O2 | F(000) = 720 |
Mr = 342.38 | Dx = 1.232 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4089 (6) Å | Cell parameters from 7807 reflections |
b = 11.4544 (14) Å | θ = 1.8–29.1° |
c = 21.9491 (17) Å | µ = 0.08 mm−1 |
β = 97.814 (6)° | T = 296 K |
V = 1845.4 (3) Å3 | Prism, orange |
Z = 4 | 0.71 × 0.49 × 0.21 mm |
Stoe IPDS 2 diffractometer | 3262 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1801 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.037 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.1°, θmin = 1.9° |
rotation method scans | h = −7→8 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −13→12 |
Tmin = 0.952, Tmax = 0.987 | l = −26→26 |
8376 measured reflections |
Refinement on F2 | 84 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.085 | H-atom parameters constrained |
wR(F2) = 0.287 | w = 1/[σ2(Fo2) + (0.1388P)2 + 0.7696P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
3262 reflections | Δρmax = 0.50 e Å−3 |
237 parameters | Δρmin = −0.45 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. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.8073 (5) | 0.5988 (3) | 0.50905 (13) | 0.0632 (9) | |
N1 | 0.7264 (5) | 0.5098 (3) | 0.47015 (13) | 0.0650 (9) | |
O2 | 0.9055 (6) | 0.8135 (3) | 0.54443 (14) | 0.0968 (12) | |
H2 | 0.866243 | 0.762928 | 0.519659 | 0.145* | |
O1 | 0.8305 (6) | 0.6961 (4) | 0.37321 (16) | 0.1135 (14) | |
C16 | 0.9521 (5) | 0.6438 (4) | 0.61058 (16) | 0.0587 (10) | |
C9 | 0.5718 (5) | 0.4721 (4) | 0.36834 (16) | 0.0604 (10) | |
C15 | 0.8727 (5) | 0.5634 (4) | 0.56320 (16) | 0.0605 (10) | |
H15 | 0.869084 | 0.484218 | 0.572232 | 0.073* | |
C8 | 0.6674 (5) | 0.5488 (3) | 0.41603 (16) | 0.0587 (10) | |
C21 | 1.0127 (6) | 0.6008 (4) | 0.66984 (15) | 0.0647 (11) | |
H21 | 1.008655 | 0.520813 | 0.676726 | 0.078* | |
C14 | 0.5475 (6) | 0.3537 (4) | 0.37911 (18) | 0.0701 (12) | |
H14 | 0.592287 | 0.321938 | 0.417175 | 0.084* | |
C20 | 1.0782 (6) | 0.6731 (5) | 0.71822 (17) | 0.0722 (12) | |
C7 | 0.7011 (7) | 0.6748 (4) | 0.39951 (17) | 0.0729 (12) | |
C17 | 0.9626 (6) | 0.7633 (4) | 0.59982 (19) | 0.0704 (12) | |
C10 | 0.5008 (6) | 0.5172 (4) | 0.31111 (17) | 0.0740 (12) | |
H10 | 0.513452 | 0.596328 | 0.303221 | 0.089* | |
C13 | 0.4574 (7) | 0.2826 (4) | 0.3337 (2) | 0.0806 (13) | |
H13 | 0.442179 | 0.203596 | 0.341196 | 0.097* | |
C12 | 0.3900 (7) | 0.3298 (5) | 0.2771 (2) | 0.0809 (14) | |
H12 | 0.329630 | 0.282317 | 0.246532 | 0.097* | |
C19 | 1.0877 (7) | 0.7906 (5) | 0.7057 (2) | 0.0844 (15) | |
H19 | 1.134050 | 0.840615 | 0.737345 | 0.101* | |
C11 | 0.4120 (7) | 0.4460 (5) | 0.26600 (19) | 0.0832 (14) | |
H11 | 0.366915 | 0.477135 | 0.227836 | 0.100* | |
C18 | 1.0317 (7) | 0.8376 (4) | 0.6481 (2) | 0.0874 (14) | |
H18 | 1.039779 | 0.917581 | 0.641626 | 0.105* | |
C22 | 1.1374 (8) | 0.6258 (6) | 0.78220 (19) | 0.0994 (18) | |
H22A | 1.044825 | 0.641737 | 0.807719 | 0.149* | |
H22B | 1.249168 | 0.662613 | 0.799408 | 0.149* | |
H22C | 1.155645 | 0.543006 | 0.780046 | 0.149* | |
C3 | 0.3300 (11) | 0.9322 (6) | 0.4407 (3) | 0.1213 (13) | |
H3 | 0.245666 | 0.989489 | 0.447121 | 0.146* | |
C2 | 0.2919 (10) | 0.8188 (5) | 0.4544 (3) | 0.1180 (12) | |
H2A | 0.188797 | 0.799054 | 0.472040 | 0.142* | |
C6 | 0.5724 (10) | 0.7645 (5) | 0.4144 (2) | 0.1031 (12) | |
C1 | 0.4177 (10) | 0.7334 (5) | 0.4404 (2) | 0.1081 (12) | |
H1 | 0.396996 | 0.655268 | 0.448600 | 0.130* | |
C5 | 0.6069 (10) | 0.8824 (5) | 0.4039 (2) | 0.1137 (12) | |
H5 | 0.710653 | 0.905524 | 0.387565 | 0.136* | |
C4 | 0.4790 (11) | 0.9644 (6) | 0.4189 (2) | 0.1204 (13) | |
H4 | 0.500278 | 1.043459 | 0.413196 | 0.144* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.066 (2) | 0.068 (2) | 0.0531 (17) | 0.0089 (17) | −0.0017 (14) | −0.0065 (15) |
N1 | 0.073 (2) | 0.069 (2) | 0.0499 (17) | 0.0104 (17) | −0.0016 (15) | −0.0052 (15) |
O2 | 0.137 (3) | 0.0681 (19) | 0.076 (2) | 0.010 (2) | −0.0158 (19) | 0.0019 (16) |
O1 | 0.123 (3) | 0.137 (3) | 0.086 (2) | −0.046 (3) | 0.033 (2) | 0.010 (2) |
C16 | 0.054 (2) | 0.070 (3) | 0.0515 (19) | 0.0107 (19) | 0.0062 (16) | −0.0051 (17) |
C9 | 0.054 (2) | 0.076 (3) | 0.0511 (19) | 0.007 (2) | 0.0080 (16) | −0.0057 (18) |
C15 | 0.059 (2) | 0.067 (2) | 0.055 (2) | 0.0119 (19) | 0.0068 (17) | −0.0041 (17) |
C8 | 0.055 (2) | 0.071 (3) | 0.0500 (19) | 0.0077 (19) | 0.0063 (16) | 0.0002 (17) |
C21 | 0.061 (3) | 0.083 (3) | 0.050 (2) | 0.001 (2) | 0.0076 (17) | −0.0030 (18) |
C14 | 0.077 (3) | 0.073 (3) | 0.058 (2) | 0.006 (2) | 0.004 (2) | −0.002 (2) |
C20 | 0.058 (3) | 0.103 (4) | 0.054 (2) | 0.003 (2) | 0.0051 (18) | −0.011 (2) |
C7 | 0.084 (3) | 0.085 (3) | 0.047 (2) | −0.020 (3) | 0.001 (2) | 0.0051 (19) |
C17 | 0.078 (3) | 0.070 (3) | 0.061 (2) | 0.012 (2) | 0.000 (2) | −0.007 (2) |
C10 | 0.087 (3) | 0.082 (3) | 0.051 (2) | 0.003 (2) | 0.0026 (19) | −0.003 (2) |
C13 | 0.083 (3) | 0.076 (3) | 0.082 (3) | 0.002 (2) | 0.010 (2) | −0.016 (2) |
C12 | 0.073 (3) | 0.101 (4) | 0.068 (3) | 0.006 (3) | 0.003 (2) | −0.029 (3) |
C19 | 0.077 (3) | 0.105 (4) | 0.068 (3) | −0.005 (3) | −0.001 (2) | −0.026 (3) |
C11 | 0.087 (4) | 0.105 (4) | 0.054 (2) | 0.008 (3) | −0.002 (2) | −0.009 (2) |
C18 | 0.098 (4) | 0.074 (3) | 0.087 (3) | 0.001 (3) | 0.001 (3) | −0.016 (2) |
C22 | 0.097 (4) | 0.147 (5) | 0.052 (2) | −0.010 (3) | 0.000 (2) | −0.007 (3) |
C3 | 0.163 (3) | 0.104 (2) | 0.0846 (19) | 0.038 (2) | −0.0283 (19) | −0.0113 (17) |
C2 | 0.157 (3) | 0.105 (2) | 0.0817 (18) | 0.036 (2) | −0.0232 (18) | −0.0129 (17) |
C6 | 0.153 (3) | 0.0836 (19) | 0.0617 (17) | 0.024 (2) | −0.0240 (17) | −0.0021 (16) |
C1 | 0.150 (3) | 0.0933 (19) | 0.0707 (18) | 0.033 (2) | −0.0220 (18) | −0.0100 (16) |
C5 | 0.165 (3) | 0.0914 (19) | 0.0731 (18) | 0.022 (2) | −0.0253 (18) | 0.0004 (16) |
C4 | 0.169 (3) | 0.097 (2) | 0.0819 (19) | 0.028 (2) | −0.0292 (19) | −0.0017 (17) |
N2—C15 | 1.287 (5) | C10—H10 | 0.9300 |
N2—N1 | 1.411 (4) | C13—C12 | 1.384 (6) |
N1—C8 | 1.289 (4) | C13—H13 | 0.9300 |
O2—C17 | 1.359 (5) | C12—C11 | 1.366 (7) |
O2—H2 | 0.8200 | C12—H12 | 0.9300 |
O1—C7 | 1.209 (5) | C19—C18 | 1.384 (7) |
C16—C17 | 1.393 (6) | C19—H19 | 0.9300 |
C16—C21 | 1.406 (5) | C11—H11 | 0.9300 |
C16—C15 | 1.452 (5) | C18—H18 | 0.9300 |
C9—C14 | 1.393 (6) | C22—H22A | 0.9600 |
C9—C10 | 1.393 (5) | C22—H22B | 0.9600 |
C9—C8 | 1.472 (5) | C22—H22C | 0.9600 |
C15—H15 | 0.9300 | C3—C4 | 1.314 (9) |
C8—C7 | 1.518 (6) | C3—C2 | 1.372 (9) |
C21—C20 | 1.382 (6) | C3—H3 | 0.9300 |
C21—H21 | 0.9300 | C2—C1 | 1.413 (8) |
C14—C13 | 1.386 (6) | C2—H2A | 0.9300 |
C14—H14 | 0.9300 | C6—C1 | 1.393 (9) |
C20—C19 | 1.377 (7) | C6—C5 | 1.399 (8) |
C20—C22 | 1.514 (6) | C1—H1 | 0.9300 |
C7—C6 | 1.469 (7) | C5—C4 | 1.405 (9) |
C17—C18 | 1.402 (6) | C5—H5 | 0.9300 |
C10—C11 | 1.379 (6) | C4—H4 | 0.9300 |
C15—N2—N1 | 114.0 (3) | C11—C12—C13 | 120.2 (4) |
C8—N1—N2 | 111.7 (3) | C11—C12—H12 | 119.9 |
C17—O2—H2 | 109.5 | C13—C12—H12 | 119.9 |
C17—C16—C21 | 118.9 (4) | C20—C19—C18 | 123.1 (4) |
C17—C16—C15 | 121.9 (3) | C20—C19—H19 | 118.5 |
C21—C16—C15 | 119.2 (4) | C18—C19—H19 | 118.5 |
C14—C9—C10 | 118.2 (4) | C12—C11—C10 | 120.3 (4) |
C14—C9—C8 | 121.4 (3) | C12—C11—H11 | 119.8 |
C10—C9—C8 | 120.4 (4) | C10—C11—H11 | 119.8 |
N2—C15—C16 | 121.8 (4) | C19—C18—C17 | 119.1 (5) |
N2—C15—H15 | 119.1 | C19—C18—H18 | 120.4 |
C16—C15—H15 | 119.1 | C17—C18—H18 | 120.4 |
N1—C8—C9 | 121.2 (4) | C20—C22—H22A | 109.5 |
N1—C8—C7 | 120.3 (3) | C20—C22—H22B | 109.5 |
C9—C8—C7 | 118.5 (3) | H22A—C22—H22B | 109.5 |
C20—C21—C16 | 122.4 (4) | C20—C22—H22C | 109.5 |
C20—C21—H21 | 118.8 | H22A—C22—H22C | 109.5 |
C16—C21—H21 | 118.8 | H22B—C22—H22C | 109.5 |
C13—C14—C9 | 120.7 (4) | C4—C3—C2 | 123.6 (7) |
C13—C14—H14 | 119.7 | C4—C3—H3 | 118.2 |
C9—C14—H14 | 119.7 | C2—C3—H3 | 118.2 |
C19—C20—C21 | 117.0 (4) | C3—C2—C1 | 116.5 (7) |
C19—C20—C22 | 121.3 (4) | C3—C2—H2A | 121.8 |
C21—C20—C22 | 121.7 (5) | C1—C2—H2A | 121.8 |
O1—C7—C6 | 123.2 (5) | C1—C6—C5 | 119.6 (6) |
O1—C7—C8 | 118.2 (5) | C1—C6—C7 | 120.5 (5) |
C6—C7—C8 | 118.6 (4) | C5—C6—C7 | 119.9 (7) |
O2—C17—C16 | 123.4 (4) | C6—C1—C2 | 121.0 (6) |
O2—C17—C18 | 117.2 (4) | C6—C1—H1 | 119.5 |
C16—C17—C18 | 119.5 (4) | C2—C1—H1 | 119.5 |
C11—C10—C9 | 120.9 (5) | C6—C5—C4 | 117.6 (7) |
C11—C10—H10 | 119.6 | C6—C5—H5 | 121.2 |
C9—C10—H10 | 119.6 | C4—C5—H5 | 121.2 |
C12—C13—C14 | 119.7 (5) | C3—C4—C5 | 121.6 (7) |
C12—C13—H13 | 120.1 | C3—C4—H4 | 119.2 |
C14—C13—H13 | 120.1 | C5—C4—H4 | 119.2 |
C15—N2—N1—C8 | −178.3 (3) | C14—C9—C10—C11 | −1.2 (6) |
N1—N2—C15—C16 | −176.5 (3) | C8—C9—C10—C11 | 179.6 (4) |
C17—C16—C15—N2 | −0.4 (6) | C9—C14—C13—C12 | −0.3 (7) |
C21—C16—C15—N2 | 176.7 (4) | C14—C13—C12—C11 | −0.1 (7) |
N2—N1—C8—C9 | −177.8 (3) | C21—C20—C19—C18 | 1.5 (7) |
N2—N1—C8—C7 | 4.3 (5) | C22—C20—C19—C18 | −178.7 (5) |
C14—C9—C8—N1 | −2.4 (6) | C13—C12—C11—C10 | −0.2 (7) |
C10—C9—C8—N1 | 176.7 (4) | C9—C10—C11—C12 | 0.9 (7) |
C14—C9—C8—C7 | 175.5 (4) | C20—C19—C18—C17 | −0.4 (8) |
C10—C9—C8—C7 | −5.3 (6) | O2—C17—C18—C19 | 178.6 (4) |
C17—C16—C21—C20 | 1.7 (6) | C16—C17—C18—C19 | −0.1 (7) |
C15—C16—C21—C20 | −175.5 (4) | C4—C3—C2—C1 | −3.8 (8) |
C10—C9—C14—C13 | 0.9 (6) | O1—C7—C6—C1 | 174.8 (4) |
C8—C9—C14—C13 | −179.9 (4) | C8—C7—C6—C1 | −3.2 (6) |
C16—C21—C20—C19 | −2.1 (6) | O1—C7—C6—C5 | −6.6 (7) |
C16—C21—C20—C22 | 178.0 (4) | C8—C7—C6—C5 | 175.3 (4) |
N1—C8—C7—O1 | 96.0 (5) | C5—C6—C1—C2 | 2.1 (7) |
C9—C8—C7—O1 | −81.9 (5) | C7—C6—C1—C2 | −179.4 (4) |
N1—C8—C7—C6 | −85.9 (5) | C3—C2—C1—C6 | 0.5 (7) |
C9—C8—C7—C6 | 96.2 (4) | C1—C6—C5—C4 | −1.6 (7) |
C21—C16—C17—O2 | −179.2 (4) | C7—C6—C5—C4 | 179.9 (4) |
C15—C16—C17—O2 | −2.1 (7) | C2—C3—C4—C5 | 4.4 (9) |
C21—C16—C17—C18 | −0.5 (6) | C6—C5—C4—C3 | −1.5 (8) |
C15—C16—C17—C18 | 176.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N2 | 0.82 | 1.94 | 2.650 (5) | 145 |
C3—H3···O2i | 0.93 | 2.54 | 3.434 (8) | 162 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Acknowledgements
Author contributions are as follows. Conceptualization, SK, ND and SOMA; synthesis, DT and AAA; writing (review and editing of the manuscript) SK, FAA and DT; formal analysis, SK and ND; crystal-structure determination, ND; validation, SK, ND and AAA, project administration, SK and SOMA.
Funding information
This study was supported by Ondokuz Mayıs University under project No. PYO·FEN.1906.19.001.
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