Solvent induced supramolecular polymorphism in Cu(II) coordination complex built from 1,2,4-triazolo[1,5-a]pyrimidine: Crystal structures and anti-oxidant activity

Chkirate, Karim; Fettach, Saad; Hafi, Mohamed El; Karrouchi, Khalid; Elotmani, Bouchaîb; Mague, Joel T.; Radi, Smaail; Faouzi, My El Abbes; Adarsh, N. N.; Essassi, El Mokhtar; Garcia, Yann

doi:10.1016/j.jinorgbio.2020.111092

Cited by 19 publications

(13 citation statements)

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“…Nitrogen-based structures have attracted increased attention in structural and inorganic chemistry in recent years because of their interesting properties (Lahmidi et al, 2018;Chkirate et al, 2020a;Taia et al, 2020;Al Ati et al, 2021). The benzimidazole family, particularly compounds containing the 2-methyl benzimidazole moiety, is important in medicinal chemistry because of their wide range of pharmacological applications including as antimicrobial and antitubercular agents (Ranjith et al, 2013), potential urease enzyme inhibitors (Menteşe et al, 2019) and antibacterial agents (Chkirate et al, 2020b).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole

Idrissi

Chkirate

Abad³

et al. 2021

Acta Crystallogr E Cryst Commun

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In the title molecule, C13H13N3O, the isoxazole ring is inclined to the benzimidazole ring at a dihedral angle of 69.28 (14)°. In the crystal, N—H...N hydrogen bonds between neighboring benzimidazole rings form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (48.8%), H...C/C...H (20.9%) and H...N/N...H (19.3%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 4.9266 eV.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole

Idrissi

Chkirate

Abad³

et al. 2021

Acta Crystallogr E Cryst Commun

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“…Nitrogen-based structures have attracted more attention in recent years because of their interesting properties in structural and inorganic chemistry (Lahmidi et al, 2018;Chkirate et al, 2020a;Taia et al, 2020;Al Ati et al, 2021). The pyrazolylacetamide family is important in medicinal chemistry because of the wide range of pharmacological applications (Deprez-Poulain et al, 2011) such as anti-inflammatory (Sunder et al, 2013), antimicrobial and anticancer (Jitender Dev et al, 2017) and as an anti-amoebic agent (Shukla et al, 2020).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and DFT study of N-(2-amino-5-methylphenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide

et al. 2021

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The title molecule, C13H16N4O, adopts an angular conformation. In the crystal a layer structure is generated by N—H...O and N—H...N hydrogen bonds together with C—H...π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (53.8%), H...C/C...H (21.7%), H...N/N...H (13.6%), and H...O/O...H (10.8%) interactions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 5.0452 eV.

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“…Nitrogen-based structures have attracted increased attention in recent years because of their interesting properties in structural and inorganic chemistry (Chkirate et al, 2019(Chkirate et al, , 2020a(Chkirate et al, ,b, 2021. The family of quinolines, particularly those containing the 2-oxoquinoline moiety, is important in medicinal chemistry because of their wide range of pharmacological applications including as potential anticancer agents (Fang et al, 2021), anti-proliferative agents (Banu et al, 2017) and as potent modulators of ABCB1-related drug resistance of mouse T-lymphoma cells (Filali Baba et al, 2020).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate

Bouzian¹,

Chkirate²,

Mague³

et al. 2021

Acta Cryst E

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The title molecule, C20H15NO3, adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the dihydroquinoline unit. In the crystal, corrugated layers are formed by C—H...O hydrogen bonds and are stacked by C—H...π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (43.3%), H...C/C...H (26.6%) and H...O/O...H (16.3%) interactions. The optimized structure calculated using density functional theory at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 4.0319 eV.

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Solvent induced supramolecular polymorphism in Cu(II) coordination complex built from 1,2,4-triazolo[1,5-a]pyrimidine: Crystal structures and anti-oxidant activity

Cited by 19 publications

References 53 publications

Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole

Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole

Crystal structure, Hirshfeld surface analysis and DFT study of N-(2-amino-5-methylphenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide

Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate

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