Antibacterial activity of 2-amino-3-cyanopyridine derivatives

Akkurt³

et al. 2022

The crystal structure of the title compound, C20H16BrN3O2, was determined using an inversion twin. Its asymmetric unit comprises two crystallographically independent molecules (A and B) being the stereoisomers. Both molecules are linked by pairs of N—H...O hydrogen bonds, forming a dimer with an R 2 2(16) ring motif. The dimers are connected by further N—H...O and N—H...N hydrogen bonds, forming chains along the c-axis direction·C—Br...π interactions between these chains contribute to the stabilization of the molecular packing. Hirshfeld surface analysis showed that the most important contributions to the crystal packing are from H...H, C...H/H...C, O...H/H...O, Br...H/H...Br and N...H/H...N interactions.

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 5-acetyl-2-amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile

Мамедов¹,

Akkurt³

et al. 2022

“…Carbon-carbon and carbon-nitrogen bond-forming reactions represent an important synthetic class in organic chemistry (Yadigarov et al, 2009;Abdelhamid et al, 2011;Yin et al, 2020;Khalilov et al, 2021). Notably, pyridine derivatives are widely applied in the discovery of biologically active molecules and multifunctional materials (Magerramov et al, 2018;Sherman & Murugan, 2015;Mamedov et al, 2020). On the other hand, the tetrahydropyridine moiety is an essential part of diverse biologically active compounds, food additives and natural products (Mateeva et al, 2005).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2-amino-4-(4-methoxyphenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile

Asadov¹,

Dobrokhotova³

et al. 2022

The central tetrahydropyridine ring of the title compound, C19H17N3O2, adopts a screw-boat conformation. In the crystal, strong C—H...O and N—H...N hydrogen bonds form dimers with R 2 2(14) and R 2 2(12) ring motifs, respectively, between consecutive molecules along the c-axis direction. Intermolecular N—H...O and C—H...O hydrogen bonds connect these dimers, forming a three-dimensional network. C—H...π interactions and π–π stacking interactions contribute to the stabilization of the molecular packing. A Hirshfeld surface analysis indicates that the contributions from the most prevalent interactions are H...H (47.1%), C...H/H...C (20.9%), O...H/H...O (15.3%) and N...H/H...N (11.4%).

“…Compounds (I) and (II) were synthesized using reported procedures [Mamedov et al (2020) and Soto et al (1981), respectively]. Colorless crystals of (I) were obtained at room temperature upon slow evaporation of a homogeneous methanol solution, while colorless needle-like crystals of (II) were obtained at room temperature upon slow evaporation from an ethanol/water (3:1) homogeneous solution.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structures and Hirshfeld surface analyses of 2-amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile hemihydrate and 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile

Naghiyev¹,

Venskovsky³

et al. 2022

In 2-amino-4-(4-bromophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile hemihydrate, C18H14BrN3O·0.5H2O, (I), pairs of molecules are linked by pairs of N—H...N hydrogen bonds, forming dimers with an R 2 2(12) ring motif. The dimers are connected by N—H...Br and O—H...O hydrogen bonds, and C—Br...π interactions, forming layers parallel to the (010) plane. 1,6-Diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile, C13H9N5O, (II), crystallizes in the triclinic space group P\overline{1} with two independent molecules (IIA and IIB) in the asymmetric unit. In the crystal of (II), molecules IIA and IIB are linked by intermolecular N—H...N and N—H...O hydrogen bonds into layers parallel to (001). These layers are connected along the c-axis direction by weak C—H...N contacts. C—H...π and C—N...π interactions connect adjacent molecules, forming chains along the a-axis direction. In (I) and (II), the stability of the packing is ensured by van der Waals interactions between the layers. In (I), Hirshfeld surface analysis showed that the most important contributions to the crystal packing are from H...H (37.9%), C...H/H...C (18.4%), Br...H/H...Br (13.3%), N...H/H...N (11.5%) and O...H/H...O (10.0%) interactions, while in (II), H...H interactions are the most significant contributors to the crystal packing (27.6% for molecule IIA and 23.1% for molecule IIB).