Nickel(II) and copper(II) complexes of N,N-dialkyl-N′-3-chlorobenzoylthiourea: Synthesis, characterization, crystal structures, Hirshfeld surfaces and antimicrobial activity

Binzet, Gün; Gümüş, İlkay; Döğen, Aylin; Flörke, Ülrich; Külcü, Nevzat; Arslan, Hakan

doi:10.1016/j.molstruc.2018.02.073

Cited by 25 publications

(20 citation statements)

References 33 publications

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“…There are a variety of motivations for investigating metal complexes of benzoylthiourea derivatives such as for catalytic applications and for anion recognition (Zhang & Schreiner, 2009;Guna-sekaran, Jerome et al, 2012;Nishikawa, 2018). Over and above these considerations, there are continuing investigations into their biological potential, such as anti-microbial (Gemili et al, 2017;Binzet et al, 2018;Saeed et al, 2018), anti-cancer (Peng et al, 2016;Barolli et al, 2017;Jeyalakshmi et al, 2019) and anti-mycobacterium tuberculosis (Plutín et al, 2016) agents. In a continuation of our on-going work on these molecules and their metal complexes Gunasekaran et al, 2017;Tan, Azizan et al, 2019), we now describe the synthesis, spectroscopic characterization and X-ray crystallographic investigation of (I).…”

Section: Chemical Contextmentioning

confidence: 99%

3,3-Bis(2-hydroxyethyl)-1-(4-nitrobenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

Tan

Jotani²,

Tiekink

2020

Acta Cryst E

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In the title compound, C12H15N3O5S, a trisubstituted thiourea derivative, the central CN2S chromophore is almost planar (r.m.s. deviation = 0.018 Å) and the pendant hydroxyethyl groups lie to either side of this plane. While to a first approximation the thione-S and carbonyl-O atoms lie to the same side of the molecule, the S—C—N—C torsion angle of −47.8 (2)° indicates a considerable twist. As one of the hydroxyethyl groups is orientated towards the thioamide residue, an intramolecular N—H...O hydrogen bond is formed which leads to an S(7) loop. A further twist in the molecule is indicated by the dihedral angle of 65.87 (7)° between the planes through the CN2S chromophore and the 4-nitrobenzene ring. There is a close match between the experimental and gas-phase, geometry-optimized (DFT) molecular structures. In the crystal, O—H...O and O—H...S hydrogen bonds give rise to supramolecular layers propagating in the ab plane. The connections between layers to consolidate the three-dimensional architecture are of the type C—H...O, C—H...S and nitro-O...π. The nature of the supramolecular association has been further analysed by a study of the calculated Hirshfeld surfaces, non-covalent interaction plots and computational chemistry, all of which point to the significant influence and energy of stabilization provided by the conventional hydrogen bonds.

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Section: Chemical Contextmentioning

confidence: 99%

3,3-Bis(2-hydroxyethyl)-1-(4-nitrobenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

Tan

Jotani²,

Tiekink

2020

Acta Cryst E

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“…While the motivations for preparing metal complexes of benzoylthioureas are varied, e.g. for anion recognition and as catalysts (Saeed et al, 2014;Zhang & Schreiner, 2009;Nishikawa, 2018), there is continuing interest in exploring their biological potential as coordination of these ligands to metals generally enhances their biological efficacy, such as anti-cancer (Peng et al, 2016;Barolli et al, 2017;Jeyalakshmi et al, 2019), anti-microbial (Gemili et al, 2017;Binzet et al, 2018;Saeed et al, 2018) and anti-mycobacterium tuberculosis (Plutín et al, 2016) activities. The present study was motivated by these applications and by previous structural studies (Gunasekaran et al, 2017; and the known catalytic applications of their cobalt complexes (Gunasekaran, Jerome et al, 2012).…”

Section: Chemical Contextmentioning

confidence: 99%

3,3-Bis(2-hydroxyethyl)-1-(4-methylbenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

Tan

Azizan

Jotani³

et al. 2019

Acta Cryst E

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In the title tri-substituted thiourea derivative, C13H18N2O3S, the thione-S and carbonyl-O atoms lie, to a first approximation, to the same side of the molecule [the S—C—N—C torsion angle is −49.3 (2)°]. The CN2S plane is almost planar (r.m.s. deviation = 0.018 Å) with the hydroxyethyl groups lying to either side of this plane. One hydroxyethyl group is orientated towards the thioamide functionality enabling the formation of an intramolecular N—H...O hydrogen bond leading to an S(7) loop. The dihedral angle [72.12 (9)°] between the planes through the CN2S atoms and the 4-tolyl ring indicates the molecule is twisted. The experimental molecular structure is close to the gas-phase, geometry-optimized structure calculated by DFT methods. In the molecular packing, hydroxyl-O—H...O(hydroxyl) and hydroxyl-O—H...S(thione) hydrogen bonds lead to the formation of a supramolecular layer in the ab plane; no directional interactions are found between layers. The influence of the specified supramolecular interactions is apparent in the calculated Hirshfeld surfaces and these are shown to be attractive in non-covalent interaction plots; the interaction energies point to the important stabilization provided by directional O—H...O hydrogen bonds.

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“…Compounds 1 and 2 were synthesized by adopting a literature procedure (Binzet et al, 2018) with slight modification: we refluxed the reactants in distilled solvents for 20 min. instead of refluxing them in anhydrous solvents for 4 h. In the first step, 4-fluorobenzoyle chloride (1 mmol) and potassium thiocyanate (1 mmol) were dissolved in acetone (10 ml) at room temperature with constant stirring for 20 minutes to obtain a white precipitate of 4-fluorophenyl isothiocyanate.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of N-(2-chlorophenylcarbamothioyl)-4-fluorobenzamide and N-(4-bromophenylcarbamothioyl)-4-fluorobenzamide

et al. 2019

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The title compounds, C14H10ClFN2OS (1) and C14H10BrFN2OS (2), were synthesized by two-step reactions. The dihedral angles between the aromatic rings are 31.99 (3) and 9.17 (5)° for 1 and 2, respectively. Compound 1 features an intramolecular bifurcated N—H...(O,Cl) link due to the presence of the ortho-Cl atom on the benzene ring, whereas 2 features an intramolecular N—H...O hydrogen bond. In the crystal of 1, inversion dimers linked by pairs of N—H...S hydrogen bonds generate R 2 2(8) loops. The extended structure of 2 features the same motif but an additional weak C—H...S interaction links the inversion dimers into [100] double columns. Hirshfeld surface analyses indicate that the most important contributors towards the crystal packing are H...H (26.6%), S...H/H.·S (13.8%) and Cl...H/H...Cl (9.5%) contacts for 1 and H...H (19.7%), C...H/H...C (14.8%) and Br...H/H...Br (12.4%) contacts for 2.

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Nickel(II) and copper(II) complexes of N,N-dialkyl-N′-3-chlorobenzoylthiourea: Synthesis, characterization, crystal structures, Hirshfeld surfaces and antimicrobial activity

Cited by 25 publications

References 33 publications

3,3-Bis(2-hydroxyethyl)-1-(4-nitrobenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

3,3-Bis(2-hydroxyethyl)-1-(4-nitrobenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

3,3-Bis(2-hydroxyethyl)-1-(4-methylbenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

Crystal structure and Hirshfeld surface analysis of N-(2-chlorophenylcarbamothioyl)-4-fluorobenzamide and N-(4-bromophenylcarbamothioyl)-4-fluorobenzamide

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