research communications
b]quinazolin-9(1H)-one
Hirshfeld surface analysis and DFT calculations of 7-bromo-2,3-dihydropyrrolo[2,1-aUniversity of Geological Sciences, Olimlar street, 64, Mirzo Ulugbek district, Tashkent, Uzbekistan, bDepartment of Chemistry, National University of Uzbekistan named after Mirzo Ulugbek, Tashkent, Uzbekistan, cS. Yunusov Institute of Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Tashkent, Uzbekistan, and dDepartment of Organic Synthesis and Bioorganic Chemistry, Samarkand State University, Samarkand, Uzbekistan
*Correspondence e-mail: a_tojiboev@yahoo.com
The molecular structure of the title compound, C11H9BrN2O, is almost planar. The benzene and pyrimidine rings are essentially coplanar, with r.m.s. deviations of 0.0130 Å, and the largest displacement is for the flap atom of the dihydropyrrole moiety [0.154 (7) Å]. Hirshfeld surface analyses revealed that the crystal packing is dominated by H⋯H, Br⋯H/H⋯Br and O⋯H/H⋯O interactions, and Br⋯Br interactions in the are also observed. Theoretical calculations using density functional theory (DFT) with the B3LYP functional basis set gave numerical parameters for the frontier molecular orbitals.
Keywords: crystal structure; 7-bromo-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one; Hirshfeld surface analysis; DFT.
CCDC reference: 2194365
1. Chemical context
Quinazolines are of significant interest for their various biological properties (Rajput et al., 2012; Ramesh et al., 2012; Khan et al., 2014; Ajani et al., 2016). This class of compounds is considered as an attractive target for medicinal chemists, because quinazoline and its derivatives are the scaffold of several potent antitumor drugs, for example the well-known erlotinib and gefitinib (Sordella et al., 2004; Raymond et al., 2000). Besides these two drugs, the Food and Drug Administration (FDA) has approved some other quinazolines as effective anticancer drugs, viz. lapatinib and vandetanib. In general, the reported biological activities of quinazolines include antibacterial, anti-inflammatory, CNS depressant, anticonvulsant, antifungal, antimalarial, anticancer properties, which make them interesting for the pharmaceutical industry (Ajani et al., 2015).
In this context, synthetic analogues of the tricyclic quinazoline-9-one-7-bromo-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one have been synthesized, amongst them the title compound with a bromine atom in position 7. In comparison with a reported literature procedure (Shakhidoyatov, 1983), this compound is now obtained in higher yields (80–88%). For this purpose, condensation of 2-amino-5-brombenzoic acid with appropriate pyrrolidin-2-one was used whereas in the literature (Shakhidoyatov, 1983), 2-amino-5-brombenzoic acid was added to the corresponding lactam mixture with a condensing agent (POCl3) at room temperature (293–298 K) and the reaction products separated by extraction after the reaction mixture was reduced to pH = 9–10 with NH4OH. As distinguished from the reported procedure, we carried out these reactions by cooling in an ice bath at a much lower temperature (273–275 K) and for a relatively longer period of time. The reaction products were finally separated by cold NH4OH at pH = 10–11. In general, the interactions of 7-bromo-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one with are well-studied (Abdurazakov et al., 2007).
Here, we report the molecular and crystal structures as well as Hirshfeld surface analysis and the frontier molecular orbitals calculated by density functional theory (DFT) with the B3LYP functional basis set.
2. Structural commentary
The molecular structure of the title compound is shown in Fig. 1. The molecule is almost planar. In particular, the benzene and pyrimidine rings are essentially coplanar, with an r.m.s. deviations of 0.0130 Å from planarity. The remaining atoms of the dihydropyrrole ring are slightly displaced from these planes, with deviations of −0.060 (5) Å for C1, −0.154 (7) Å for flap atom C2, and 0.060 (6) Å for C3. The acyclic C7—Br1 bond length 1.900 (3) Å is consistent with the data for other Br-substituted tricyclic quinazolinone derivatives (Mukarramov et al., 2009; Tozhiboev et al., 2007a; D'yakonov et al., 1992; Okmanov et al., 2009; Pereira et al., 2005).
3. Supramolecular features
In the crystal, molecules participate in centrosymmetric halogen-bonding dimers with Br⋯Br intermolecular contacts of 3.5961 (5) Å, which is shorter than the sum of van der Waals radii (Bondi et al., 1964) of two bromine atoms (3.66 Å). The C7—Br⋯Br angle amounts to 166.70 (14)°. The molecules also engage in weak C7—Br⋯Cg interactions, with Br⋯Cg1(2 − x, 1 − y, 1 − z) = 3.6428 (15) Å, forming a layered network (Fig. 2). Additional π–π stacking (Fig. 3) occurs between the aromatic rings of neighbouring molecules, with the distance between the centroids Cg2⋯Cg2i being 3.9969 (14) Å [symmetry code: (i) 1 − x, 1 − y, 1 − z] and a ring slippage of 1.569 Å, and Cg2⋯Cg3ii being 3.7513 (16) Å [symmetry code: (ii) 2 − x, 1 − y, 1 − z] and a ring slippage of 1.194 Å. Both short intermolecular contacts help to stack parallel molecules along [100]. The resulting two-dimensional network extends parallel to (002), with neighbouring layers linked through C1—H1B⋯N4 short intermolecular contacts, H1B⋯N4(x, − y, + z) = 2.73 Å, C1—H1B⋯N4(x, − y, + z) = 169°, to form the full three-dimensional structure (Fig. 4).
4. Hirshfeld surface analysis
In order to quantify the intermolecular interactions in the crystal of the title compound, a Hirshfeld surface (HS) analysis (Spackman et al., 2009) was performed and associated two-dimensional fingerprint plots (McKinnon et al., 2007) were generated with the program CrystalExplorer (Spackman et al., 2021). The HS mapped over dnorm is depicted in Fig. 5, which shows the most prominent intermolecular interactions as red spots corresponding to the Br⋯Br, C—H⋯O and N—H⋯O contacts. The two-dimensional fingerprint plot for all contacts is given in Fig. 6a. H⋯H contacts are responsible for the largest contribution (37.2%) to the Hirshfeld surface (Fig. 6b). Besides these contacts, Br⋯H/H⋯Br (19.6%), O⋯H/H⋯O (11.3%), N⋯H/H⋯N (8.1%) and C⋯H/H⋯C (6.9%) interactions contribute significantly to the total Hirshfeld surface; their decomposed fingerprint plots are shown in Fig. 6c–f. The contributions of further contacts are only minor and amount to N⋯C/C⋯N (3.5%), O⋯C/C⋯O (2.0%), Br⋯C/C⋯Br (0.9%), Br⋯Br (0.8%), O⋯N/N⋯O (0.5%) and Br⋯N/N⋯Br (0.3%).
5. Frontier molecular orbitals
DFT was used to calculate the frontier molecular orbitals (FMOs, Fig. 7), which give important details of how a molecule interacts with other species, for example in terms of molecular reactivity and the ability of a molecule to absorb light. From the highest occupied molecular orbital (HOMO) electrons can be donated to the lowest unoccupied molecular orbital (LUMO). Moreover, the energy of the HOMO is directly related to the while the LUMO energy is directly related to the and the resulting energy difference (or energy gap) between HOMO and LUMO gives information about the stability of a molecule. In the case where the energy gap is small, the molecule is highly polarizable and has a high chemical reactivity. By using the HOMO and LUMO energy values of a molecule, its (c), chemical hardness (h) and chemical softness (s) can be calculated as follows: c = (I + A)/2; h = (I - A)/2; s = 1/2h, where I and A are the and respectively, where I = –EHOMO and A = –ELUMO (Pir et al., 2014; Azizov et al., 2021).
EHOMO and ELUMO, (c), hardness (h), potential (m), (w) and softness (s) for the title molecule were calculated at the DFT/B3LYP level using the 6-311++G(d,p) basis set (Table 1). The values of h and s are significant for the evaluation of both reactivity and stability. The electron transition from the HOMO to the LUMO energy level is shown in Fig. 7. The energy band gap [ΔE = ELUMO − EHOMO] of the molecule is 4.8208 eV, the frontier molecular orbital energies EHOMO and ELUMO being −6.4559 and −1.6351 eV, respectively. The high value of the band gap (4,8208 eV) indicates the relatively high stability of the title molecule.
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6. Database survey
A search in the Cambridge Structural Database (CSD, version 2022; Groom et al., 2016) gave four matches of molecules containing the 2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one moiety with a similar conformation to that in the title structure: deoxyvasicinone (TEFGEQ; Turgunov et al., 1995), deoxyvasicinonium chloride (TEFGIU; Turgunov et al., 1995), bis(deoxyvasicinonium) tetrachloridocobaltate(II) (TEFGOA; Turgunov et al., 1995) and 4-oxo-2,3-tetramethylene-3,4-dihydroquinazolinium 2,3-tetramethylene-3,4-dihydroquinazol-4-one hemikis(oxalate) oxalic acid solvate (TITGUZ; Tozhiboev et al., 2007b). A search for compounds substituted in position 7 of 2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one moiety gave only two hits: N-(9-oxo-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-7-yl)propanamide sesquihydrate (GABJAX; Elmuradov et al., 2016) and 3b-hydroxy-7-methoxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one monohydrate (HIHLIT; Magotra et al., 1996). Comparing the listed structures with that of the title compound gave analogous complanarities of the benzene and pyrimidine rings. In the case of structures TEFGEQ, GABJAX and HIHLIT they have also similarities regarding π–π stacking interactions.
7. Synthesis and crystallization
The reaction scheme to yield the title compound is shown in Fig. 8. To a mixture of 4.32 g (20 mmol) 2-amino-5-bromobenzoic acid and 2.72 g (32 mmol) pyrrolidin-2-one, 21.8 g (13 ml) (d = 1.675) (0.142 mol) of phosphoroxychloride were added dropwise over 1 h at 273–275 K. The reaction mixture was then heated at 368–371 K for 2 h, it was subsequently cooled and finally poured over ice. The temperature of the mixture was kept at around 273–275 K. When the reaction mixture was completely decomposed, it was brought to pH = 10–11 with 25%wt ammonium hydroxide solution. The light-yellow precipitate was filtered off, dried and recrystallized from methanol. The yield of the product was 4.35 g (82%), m.p. 431–433 K (literature, m.p. = 430–431 K; Shakhidoyatov, 1983).
1H NMR (400 Mz, CDCl3, δ, ppm): 8.4 (1H, d, J = 2.4, H-8), 7.8 (1H, dd, J = 2.4, J = 8.8, H-6), 7.5 (1H, d, J = 8.8, H-5), 4.2 (2H, q, J = 7.2, H-1), 3.18 (2H, t, J = 7.6, H-3), 2.31 (2H, m, H-2).
8. Refinement
Crystal data, data collection and structure . H atoms attached to C were positioned geometrically, with C—H = 0.93 Å (for aromatic) or C—H = 0.97 Å (for methylene H atoms), and were refined with Uiso(H) = 1.2Ueq(C).
details are summarized in Table 2Supporting information
CCDC reference: 2194365
https://doi.org/10.1107/S2056989022007800/wm5655sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022007800/wm5655Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989022007800/wm5655Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2020); cell
CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).C11H9BrN2O | F(000) = 528 |
Mr = 265.11 | Dx = 1.737 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 7.5654 (3) Å | Cell parameters from 5905 reflections |
b = 11.4972 (2) Å | θ = 3.8–71.3° |
c = 12.1025 (3) Å | µ = 5.30 mm−1 |
β = 105.583 (3)° | T = 296 K |
V = 1013.99 (5) Å3 | Prismatic, colourless |
Z = 4 | 0.45 × 0.10 × 0.10 mm |
XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer | 1959 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 1770 reflections with I > 2σ(I) |
Detector resolution: 10.0000 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 71.5°, θmin = 5.4° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020) | h = −9→9 |
Tmin = 0.400, Tmax = 1.000 | k = −14→13 |
9036 measured reflections | l = −14→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0459P)2 + 0.6636P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max = 0.005 |
S = 1.08 | Δρmax = 0.61 e Å−3 |
1959 reflections | Δρmin = −0.56 e Å−3 |
137 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0045 (4) |
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 | ||
Br | 0.90737 (5) | 0.85845 (3) | 0.51410 (4) | 0.0772 (2) | |
O | 0.6024 (3) | 0.46212 (19) | 0.28785 (15) | 0.0704 (6) | |
C1 | 0.5525 (4) | 0.2291 (2) | 0.3474 (2) | 0.0524 (6) | |
H1A | 0.615715 | 0.217862 | 0.288281 | 0.063* | |
H1B | 0.424182 | 0.245293 | 0.311148 | 0.063* | |
C2 | 0.5725 (5) | 0.1238 (3) | 0.4234 (3) | 0.0646 (8) | |
H2A | 0.660804 | 0.070068 | 0.406688 | 0.077* | |
H2B | 0.455714 | 0.084094 | 0.411100 | 0.077* | |
C3 | 0.6385 (5) | 0.1665 (2) | 0.5467 (2) | 0.0573 (7) | |
H3A | 0.541287 | 0.160567 | 0.584874 | 0.069* | |
H3B | 0.742854 | 0.121317 | 0.589288 | 0.069* | |
C3A | 0.6916 (4) | 0.2907 (2) | 0.53807 (19) | 0.0428 (5) | |
N4 | 0.7726 (4) | 0.35675 (17) | 0.62262 (17) | 0.0503 (5) | |
C4A | 0.8027 (3) | 0.4710 (2) | 0.59434 (19) | 0.0424 (5) | |
C5 | 0.8937 (4) | 0.5471 (2) | 0.6820 (2) | 0.0569 (7) | |
H5 | 0.932797 | 0.519968 | 0.757050 | 0.068* | |
C6 | 0.9258 (4) | 0.6610 (2) | 0.6588 (2) | 0.0554 (7) | |
H6 | 0.986151 | 0.710837 | 0.717397 | 0.066* | |
C7 | 0.8667 (4) | 0.7005 (2) | 0.5464 (2) | 0.0490 (6) | |
C8 | 0.7793 (4) | 0.6286 (2) | 0.4582 (2) | 0.0486 (6) | |
H8 | 0.742035 | 0.656476 | 0.383367 | 0.058* | |
C8A | 0.7471 (3) | 0.5135 (2) | 0.48227 (19) | 0.0403 (5) | |
C9 | 0.6560 (3) | 0.4355 (2) | 0.38867 (19) | 0.0451 (5) | |
N10 | 0.6368 (3) | 0.32406 (18) | 0.42522 (15) | 0.0405 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.0940 (3) | 0.0341 (2) | 0.1020 (4) | −0.00671 (14) | 0.0235 (2) | 0.00799 (14) |
O | 0.1104 (17) | 0.0553 (12) | 0.0345 (9) | 0.0020 (11) | 0.0007 (10) | 0.0064 (8) |
C1 | 0.0651 (16) | 0.0489 (15) | 0.0402 (12) | −0.0045 (12) | 0.0089 (11) | −0.0130 (11) |
C2 | 0.090 (2) | 0.0478 (16) | 0.0519 (16) | −0.0179 (15) | 0.0121 (15) | −0.0119 (12) |
C3 | 0.088 (2) | 0.0401 (13) | 0.0432 (13) | −0.0170 (13) | 0.0171 (13) | −0.0026 (11) |
C3A | 0.0572 (14) | 0.0365 (12) | 0.0347 (11) | −0.0038 (10) | 0.0121 (10) | 0.0004 (9) |
N4 | 0.0768 (15) | 0.0375 (12) | 0.0338 (10) | −0.0096 (9) | 0.0099 (10) | −0.0008 (8) |
C4A | 0.0548 (13) | 0.0338 (12) | 0.0377 (11) | −0.0018 (10) | 0.0110 (10) | 0.0000 (9) |
C5 | 0.0807 (19) | 0.0420 (14) | 0.0412 (12) | −0.0082 (13) | 0.0047 (12) | −0.0026 (11) |
C6 | 0.0657 (16) | 0.0411 (13) | 0.0557 (15) | −0.0073 (12) | 0.0100 (13) | −0.0097 (11) |
C7 | 0.0530 (14) | 0.0315 (12) | 0.0638 (15) | 0.0004 (10) | 0.0177 (12) | 0.0019 (11) |
C8 | 0.0595 (15) | 0.0385 (13) | 0.0476 (13) | 0.0059 (10) | 0.0142 (11) | 0.0086 (10) |
C8A | 0.0473 (12) | 0.0363 (12) | 0.0375 (11) | 0.0042 (9) | 0.0116 (9) | 0.0011 (9) |
C9 | 0.0571 (14) | 0.0407 (13) | 0.0354 (11) | 0.0060 (10) | 0.0090 (10) | 0.0027 (9) |
N10 | 0.0515 (11) | 0.0373 (10) | 0.0317 (9) | −0.0017 (8) | 0.0093 (8) | −0.0033 (8) |
Br—C7 | 1.900 (3) | C3A—N10 | 1.371 (3) |
O—C9 | 1.217 (3) | N4—C4A | 1.392 (3) |
C1—N10 | 1.471 (3) | C4A—C8A | 1.396 (3) |
C1—C2 | 1.503 (4) | C4A—C5 | 1.404 (3) |
C1—H1A | 0.9700 | C5—C6 | 1.375 (4) |
C1—H1B | 0.9700 | C5—H5 | 0.9300 |
C2—C3 | 1.522 (4) | C6—C7 | 1.389 (4) |
C2—H2A | 0.9700 | C6—H6 | 0.9300 |
C2—H2B | 0.9700 | C7—C8 | 1.371 (4) |
C3—C3A | 1.494 (4) | C8—C8A | 1.391 (3) |
C3—H3A | 0.9700 | C8—H8 | 0.9300 |
C3—H3B | 0.9700 | C8A—C9 | 1.464 (3) |
C3A—N4 | 1.290 (3) | C9—N10 | 1.376 (3) |
N10—C1—C2 | 104.5 (2) | N4—C4A—C5 | 118.8 (2) |
N10—C1—H1A | 110.8 | C8A—C4A—C5 | 118.3 (2) |
C2—C1—H1A | 110.8 | C6—C5—C4A | 121.1 (2) |
N10—C1—H1B | 110.8 | C6—C5—H5 | 119.4 |
C2—C1—H1B | 110.8 | C4A—C5—H5 | 119.4 |
H1A—C1—H1B | 108.9 | C5—C6—C7 | 118.9 (2) |
C1—C2—C3 | 107.0 (2) | C5—C6—H6 | 120.6 |
C1—C2—H2A | 110.3 | C7—C6—H6 | 120.6 |
C3—C2—H2A | 110.3 | C8—C7—C6 | 121.8 (2) |
C1—C2—H2B | 110.3 | C8—C7—Br | 119.1 (2) |
C3—C2—H2B | 110.3 | C6—C7—Br | 119.1 (2) |
H2A—C2—H2B | 108.6 | C7—C8—C8A | 119.0 (2) |
C3A—C3—C2 | 105.3 (2) | C7—C8—H8 | 120.5 |
C3A—C3—H3A | 110.7 | C8A—C8—H8 | 120.5 |
C2—C3—H3A | 110.7 | C8—C8A—C4A | 120.8 (2) |
C3A—C3—H3B | 110.7 | C8—C8A—C9 | 119.6 (2) |
C2—C3—H3B | 110.7 | C4A—C8A—C9 | 119.6 (2) |
H3A—C3—H3B | 108.8 | O—C9—N10 | 121.4 (2) |
N4—C3A—N10 | 125.3 (2) | O—C9—C8A | 125.6 (2) |
N4—C3A—C3 | 125.9 (2) | N10—C9—C8A | 112.97 (19) |
N10—C3A—C3 | 108.8 (2) | C3A—N10—C9 | 123.4 (2) |
C3A—N4—C4A | 115.8 (2) | C3A—N10—C1 | 113.1 (2) |
N4—C4A—C8A | 122.9 (2) | C9—N10—C1 | 123.41 (19) |
N10—C1—C2—C3 | 9.8 (4) | C5—C4A—C8A—C8 | −0.7 (4) |
C1—C2—C3—C3A | −11.4 (4) | N4—C4A—C8A—C9 | −1.2 (4) |
C2—C3—C3A—N4 | −172.4 (3) | C5—C4A—C8A—C9 | 178.5 (2) |
C2—C3—C3A—N10 | 8.8 (3) | C8—C8A—C9—O | −0.4 (4) |
N10—C3A—N4—C4A | 0.9 (4) | C4A—C8A—C9—O | −179.6 (3) |
C3—C3A—N4—C4A | −177.8 (3) | C8—C8A—C9—N10 | 178.8 (2) |
C3A—N4—C4A—C8A | 1.0 (4) | C4A—C8A—C9—N10 | −0.3 (3) |
C3A—N4—C4A—C5 | −178.7 (3) | N4—C3A—N10—C9 | −2.6 (4) |
N4—C4A—C5—C6 | −179.6 (3) | C3—C3A—N10—C9 | 176.2 (2) |
C8A—C4A—C5—C6 | 0.7 (4) | N4—C3A—N10—C1 | 178.4 (3) |
C4A—C5—C6—C7 | 0.0 (5) | C3—C3A—N10—C1 | −2.7 (3) |
C5—C6—C7—C8 | −0.7 (4) | O—C9—N10—C3A | −178.6 (3) |
C5—C6—C7—Br | 179.0 (2) | C8A—C9—N10—C3A | 2.1 (3) |
C6—C7—C8—C8A | 0.8 (4) | O—C9—N10—C1 | 0.3 (4) |
Br—C7—C8—C8A | −179.02 (19) | C8A—C9—N10—C1 | −179.0 (2) |
C7—C8—C8A—C4A | −0.1 (4) | C2—C1—N10—C3A | −4.5 (3) |
C7—C8—C8A—C9 | −179.2 (2) | C2—C1—N10—C9 | 176.5 (2) |
N4—C4A—C8A—C8 | 179.6 (2) |
Parameters | DFT/B3LYP |
Total energy TE (a.u.) | -3183.662028 |
EHOMO (eV) | -6.4559 |
ELUMO (eV) | -1.6351 |
Energy gap, ΔE (eV) | 4.8208 |
Dipole moment, µ (Debye) | 4.6478 |
Ionization potential, I (eV) | 6.4559 |
Electron affinity, A | 1.6351 |
Electronegativity, χ | 4.0455 |
Hardness, η | 2.4104 |
Electrophilicity index, ω | 3.3949 |
Softness, σ | 0.2074 |
Acknowledgements
The authors thank the Institute of Bioorganic Chemistry of Academy Sciences of Uzbekistan, Tashkent, Uzbekistan for providing the single-crystal XRD facility.
Funding information
Funding for this research was provided by: the Ministry of Innovative Development of Uzbekistan (grant No. F-FA-2021-408 "Study of the laws of introducing of pharmacophore fragments into the molecule on the basis of modern cross-coupling and heterocyclization reactions").
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