Crystal structure and Hirshfeld surface analysis of 4-[4-(1<i>H</i>-benzo[<i>d</i>]imidazol-2-yl)phenoxy]phthalonitrile monohydrate

Şen, Pınar; Kansız, Sevgi; Dege, Necmi; Iskenderov, Turganbay S.; Yıldız, Salih

doi:10.1107/s2056989018008745

Cited by 11 publications

(9 citation statements)

References 14 publications

(14 reference statements)

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“…The bond lengths of the cyano groups, 1.132 (6) and 1.137 (6) Å , for C21 N4 and C20 N3, respectively, conform well with literature values (Saraçog lu et al, 2011). The corresponding C-C N angles [179.4 (6) and 177.9 (7) ] are almost linear and are also in good agreement with literature values (Saraçog lu et al, 2011;Sen et al, 2018a). The C-C bond lengths of the phenyl rings are in the normal range of 1.356 (5)-1.395 (6) Å , i.e.…”

Section: Structural Commentarysupporting

confidence: 89%

Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate

et al. 2019

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This work presents the synthesis and structural characterization of [4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile, a phthalonitrile derivative carrying a benzimidazole moiety. The compound crystallizes as its dimethyl sulfoxide monosolvate, C21H12N4O·(CH3)2SO. The dihedral angle between the two fused rings in the heterocyclic ring system is 2.11 (1)°, while the phenyl ring attached to the imidazole moiety is inclined by 20.7 (1)° to the latter. In the crystal structure, adjacent molecules are connected by pairs of weak intermolecular C—H...N hydrogen bonds into inversion dimers. N—H...O and C—H...O hydrogen bonds with R 2 1(7) graph-set motifs are also formed between the organic molecule and the disordered dimethyl sulfoxide solvent [occupancy ratio of 0.623 (5):0.377 (5) for the two sites of the sulfur atom]. Hirshfeld surface analysis and fingerprint plots were used to investigate the intermolecular interactions in the crystalline state.

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Section: Structural Commentarysupporting

confidence: 89%

Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate

et al. 2019

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“…The d e , d i , and d norm , surfaces were mapped over the normal range (Figure 3a). Red reigions represent the intermolecular and interatomic forces caused by strong hydrogen bonding [35], thus shows the C-H···O hydrogen bonds in the BiPhAAP. A fixed color scale of -0.2156 (red) to 1.3214 (blue) a.u.…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

A Synthetic, Spectroscopic, Theoretical and Biological Perspective on a Novel Schiff Base Included 4-Aminoantipyrine

Ertürk

2019

Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi

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A novel Schiff base, 4-(([1,1'-biphenyl]-4-ylmethylene)amino)-1,5-dimethyl-2phenyl-1,2-dihydro-3H-pyrazol-3-one (BiPhAAP), obtained from biphenyl carboxaldehyde with 4-aminoantipyrine was characterized using elemental analysis, FT-IR, and 1 H and 13 C NMR spectroscopic methods. In addition to the spectroscopic findings, geometrical descriptions and the extent of surface interactions in the compound were determined by X-ray single crystallographic and Molecular Hirshfeld surface (MHS) analysis techniques. The distinctions between experimental and calculated FT-IR results have proved the presence of intra-molecular (C-H….O type) hydrogen bonds in the crystal structure. The in vitro antimicrobial potential, which was studied against two Gram-negative (Escherichia coli and Proteus vulgaris) and two Gram-positive (Bacillus subtilis and Micrococcus luteus) bacterial strains, and three yeast strains (Candida albicans, Aspergillus niger and Candida globrata) was examined by using the agar well diffusion method at concentrations of 250, 125 and 62.5 mg/mL. The in vitro antioxidant activities of this compound were estimated by five different antioxidant assays (DPPH radical scavenging, reducing power, metal chelating activity, superoxide scavenging, and total antioxidant). Cytotoxic activity of the new compound was sought against human breast carcinoma cells (MCF-7). The IC 50 values were established with respect to the MTT test.

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“…Figure 7 illustrates Hirshfeld surfaces of C30H36N2O2 with mapped dnorm, di and de. The red spots over Hirshfeld surface point out the inter-contacts included in hydrogen bonds (27)(28)(29)(30)(31). The surfaces of 3D dnorm plotted with a color scale of -0.103 to 1.501 Å with a standard (high) surface resolution.…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Synthesis, Molecular Structure, Hirshfeld Surface Analysis, Spectroscopic and Computational Studies (DFT) of 6,6'-((1E,1'E)- (1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(2- (tert-butyl)-4-methylphenol)

Şen

Kansız

Dege

2019

Journal of the Turkish Chemical Society Section A: Chemistry

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Schiff bases have been used in biological processes and as chelating agents for several decades. In this work, a Schiff base compound was obtained with the condensation of ophenylenediamine and an aromatic aldehyde. The structures were confirmed by spectroscopic methods. The molecular structure of the compound was also confirmed using X-ray single-crystal data. And also we made the parameters calculate theoretically the DFT-B3LYP method. For C30H36N2O2 compound, HOMO-LUMO and MEP surface were composed by making use of C30H36N2O2. The theoretical results are in a good concurrence with the empirical values. To analyze interactions existing in crystal packing, 2D fingerprint plots and Hirshfeld surface analyses were performed, signifying that the contributions are H•••H (71.2%), H•••C/C•••H (18.7%) and C•••C (4.8%) contacts.

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Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile monohydrate

Abstract: In the crystal, strong O—H⋯N hydrogen bonds link the molecules into supramolecular chains propagating along the c-axis direction.

Cited by 11 publications

References 14 publications

Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate

Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate

A Synthetic, Spectroscopic, Theoretical and Biological Perspective on a Novel Schiff Base Included 4-Aminoantipyrine

Synthesis, Molecular Structure, Hirshfeld Surface Analysis, Spectroscopic and Computational Studies (DFT) of 6,6'-((1E,1'E)- (1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(2- (tert-butyl)-4-methylphenol)

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Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile monohydrate

Abstract: In the crystal, strong O—H⋯N hydrogen bonds link the mol­ecules into supra­mol­ecular chains propagating along the c-axis direction.

Cited by 11 publications

References 14 publications

Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate

Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate

A Synthetic, Spectroscopic, Theoretical and Biological Perspective on a Novel Schiff Base Included 4-Aminoantipyrine

Synthesis, Molecular Structure, Hirshfeld Surface Analysis, Spectroscopic and Computational Studies (DFT) of 6,6'-((1E,1'E)- (1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(2- (tert-butyl)-4-methylphenol)

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Abstract: In the crystal, strong O—H⋯N hydrogen bonds link the molecules into supramolecular chains propagating along the c-axis direction.