2-(Naphthalen-1-yl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5(4<i>H</i>)-one

Gündoğdu, Cevher; Alp, Serap; Ergün, Yavuz; Tercan, Barış; Hökelek, Tuncer

doi:10.1107/s1600536811015340

Acta Cryst E

2011

DOI: 10.1107/s1600536811015340

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2-(Naphthalen-1-yl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5(4H)-one

Cevher Gündoğdu

Serap Alp

Yavuz Ergün

et al.

Abstract: In the title compound, C24H15NO2, the oxazole ring is oriented at dihedral angles of 10.09 (4) and 6.04 (4)° with respect to the mean planes of the naphthalene ring systems, while the two naphthalene ring systems make a dihedral angle of 4.32 (3)°. Intramolecular C—H⋯N hydrogen bonds link the oxazole N atom to the naphthalene ring systems. In the crystal, intermolecular weak C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. π–π contacts between the oxazole and naphthalene rings and betwee… Show more

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“…°; C1-C6 / C11-C20 2.09(11)°]. The C=O [1.200(3) Å], C=C [1.363(2) Å], and C=N [1.288(3) Å] bond lengths are similar to those reported for the (Z)-4-(2,4,6trimethyl)benzylidene-2-phenyloxazolin-5-one[i.e., 1.193, 1.136, and 1.280 Å, respectively], 27 (Z)-2-(naphthalen-1-yl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5(4H)-one [i.e., 1.2015(18), 1.348(2), and 1.2880(18) Å, respectively] 28. …”

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Crystal structure and Hirshfeld surface analysis of (Z)-2-phenyl-4-((4,6,8-trimethylazulen-1-yl)methylene)oxazol-5(4H)-one

RĂDUCĂ,

Raț,

CRISTEA

2023

Rev.Roum.Chim.

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The molecular structure of (Z)-2-phenyl-4-((4,6,8-trimethylazulen-1-yl)methylene)oxazol-5(4H)-one (1) was determined single-crystal X-ray diffraction. The crystal presents a monoclinic crystal system, space group P21/n, a = 7.0706(3) Å, b = 18.7978(7) Å, c = 13.7059(7) Å, β = 103.013(5) °, V = 1774.89(14) Å3. In the crystals of 1, are present strong π-π stacking interactions, with an average distance of 3.54 Å between centroids.

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mentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (Z)-2-phenyl-4-((4,6,8-trimethylazulen-1-yl)methylene)oxazol-5(4H)-one

RĂDUCĂ,

Raț,

CRISTEA

2023

Rev.Roum.Chim.

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Dihydrooxazolones and dihydroimidazolones derived from acylglycines: syntheses, molecular structures and supramolecular assembly

et al. 2015

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Syntheses and structures are described for some alkylidene-substituted dihydrooxazolones and dihydroimidazoles derived from simple acylglycines. A second, triclinic, polymorph of 4-benzylidene-2-(4-methylphenyl)-1,3-oxazol-5(4H)-one, C17H13NO2, (I), has been identified and the structure of 2-methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one, C9H7NO2S, (II), has been rerefined taking into account the orientational disorder of the thienyl group in each of the two independent molecules. The reactions of phenylhydrazine with 2-phenyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one or 2-(4-methylphenyl)-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one yield, respectively, 3-anilino-2-phenyl-5-[(thiophen-2-yl)methylidene]-3,5-dihydro-4H-imidazol-4-one, C10H15N3OS, (III), and 3-anilino-2-(4-methylphenyl)-5-[(thiophen-2-yl)methylidene]-3,5-dihydro-4H-imidazol-4-one, C21H17N3OS, (IV), which both exhibit orientational disorder in their thienyl groups. The reactions of 2-phenyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one with hydrazine hydrate or with water yield, respectively, N-[3-hydrazinyl-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl]benzamide and 2-(benzoylamino)-3-(thiophen-2-yl)prop-2-enoic acid, which in turn react, respectively, with thiophene-2-carbaldehyde to form 2-phenyl-5-[(thiophen-2-yl)methylidene]-3-{[(E)-(thiophen-2-yl)methylidene]amino}-3,5-dihydro-4H-imidazol-4-one, C19H13N3OS2, (V), which exhibits orientational disorder in only one of its thienyl groups, and with methanol to give methyl (2Z)-2-(benzoylamino)-3-(thiophen-2-yl)prop-2-enoate, C15H13NO3S, (VI). There are no direction-specific intermolecular interactions in the crystal structure of the triclinic polymorph of (I), but the molecules of (II) are linked by two independent C-H···O hydrogen bonds to form C2(2)(14) chains. Compounds (III) and (IV) both form centrosymmetric R2(2)(10) dimers built from N-H···O hydrogen bonds, while compound (V) forms a centrosymmetric R2(2)(10) dimer built from C-H···O hydrogen bonds. In the structure of compound (VI), a combination of N-H···O and C-H···π(arene) hydrogen bonds links the molecules into sheets. Comparisons are made with some similar compounds.

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Crystal structure of 2-methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one

et al. 2015

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The asymmetric unit of the title compound, C9H7NO2S, contains two crystallographically independent molecules (A and B). Both molecules are almost planar [maximum deviations = 0.047 (1) and 0.090 (1) Å, respectively, for the S atoms] with the oxazole and thiophene rings being inclined to one another by 2.65 (16)° in molecule A and by 4.55 (15)° in molecule B. In the crystal, the individual molecules are linked via C—H⋯O hydrogen bonds, forming –A–B–A–B– chains along the [10-1] direction. The chains are linked via C—H⋯π and π–π interactions [intercentroid distances = 3.767 (2) and 3.867 (2) Å] involving inversion-related oxazole and thiophene rings in both molecules, forming a three-dimensional structure.

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2-(Naphthalen-1-yl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5(4H)-one

Cited by 3 publications

References 13 publications

Crystal structure and Hirshfeld surface analysis of (Z)-2-phenyl-4-((4,6,8-trimethylazulen-1-yl)methylene)oxazol-5(4H)-one

Crystal structure and Hirshfeld surface analysis of (Z)-2-phenyl-4-((4,6,8-trimethylazulen-1-yl)methylene)oxazol-5(4H)-one

Dihydrooxazolones and dihydroimidazolones derived from acylglycines: syntheses, molecular structures and supramolecular assembly

Crystal structure of 2-methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one

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