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    A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors
    (Int Union Crystallography, 2015) Salian, Vinutha V.; Narayana, Badiadka; Yathirajan, Hemmige S.; Akkurt, Mehmet; Celik, Omer; Ersanli, Cem Cuneyt; Glidewell, Christopher
    Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)-1-(2,4- Dichlorophenyl)-3-[4-(prop-1-en-2-yl)phenyl]prop-2-en-1-one, C18H14Cl2O, (I), prepared from 4-(prop-1-en-2-yl)benzaldehyde and 2,4-dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)-3-(4-chlorophenyl)-1-(4-fluorophenyl)-prop-2-en-1-one reacts with acetone to produce (5RS)-3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]cyclohex-2-en-1-one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3-oxobutanoate to give methyl (1RS, 6SR)-4-(4-chlorophenyl)-6-[4-(propan-2-yl)phenyl]-2-oxocyclohex-3-ene-1-carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, of ethyl (1RS, 6SR)-6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4 ''-bromo-4-fluoro-5'-hydroxy-1,1':3',1 ''-terphenyl-4'-carboxylate, C21H16BrFO3, (IV), which crystallizes with Z' = 2 in the space group P (1) over bar. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot pi(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion-related pairs of C-H center dot center dot center dot O hydrogen bonds and the other from inversion-related pairs of C-H center dot center dot center dot pi(arene) hydrogen bonds. Comparisons are made with related compounds.
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    Dihydrooxazolones and dihydroimidazolones derived from acylglycines: syntheses, molecular structures and supramolecular assembly
    (Int Union Crystallography, 2015) Subbulakshmi, Karanth N.; Narayana, Badiadka; Yathirajan, Hemmige S.; Akkurt, Mehmet; Celik, Omer; Ersanli, Cem Cuneyt; Glidewell, Christopher
    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-1en-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 center dot center dot center dot O hydrogen bonds to form C-2(2)(14) chains. Compounds (III) and (IV) both form centrosymmetric R-2(2)(10) dimers built from N-H center dot center dot center dot O hydrogen bonds, while compound (V) forms a centrosymmetric R-2(2)(10) dimer built from C-H center dot center dot center dot O hydrogen bonds. In the structure of compound (VI), a combination of N-H center dot center dot center dot O and C-H center dot center dot center dot pi (arene) hydrogen bonds links the molecules into sheets. Comparisons are made with some similar compounds.
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    Syntheses, crystal structures, spectroscopic and thermal characterisations of new homophthalate compounds
    (Pergamon-Elsevier Science Ltd, 2015) Orhan, Oguzhan; Colak, Alper Tolga; Sahin, Onur; Tunc, Tuncay; Celik, Omer
    In this study, four new M(II)-homophthalate complexes with 2,2'-bipyridine (bipy). N,N-dimethylethylenediamine (dmen), imidazole (im) and 1,10-phenanthroline (phen), namely [Mn(hmph)(bipy)(H2O)(2)](n) (1), [Ni(hmph)(dmen)(2)(H2O)]center dot H2O (2), [Cu(hmph)(im)(2)](n) (3) and [Cu(phen)(2)Cl]center dot(Hhmph)center dot(H(2)hmph) (4) (H(2)hmph = homophthalic acid) have been synthesised. Elemental and thermal analyses and IR spectroscopic studies have been performed to characterise the complexes. The molecular structures of the complexes have been determined by single crystal X-ray diffraction. The geometries around the Mn(II) (1) and Ni(II) (2) ions are distorted octahedrons. Each Cu(II) ion exhibits penta-coordination with a distorted square-pyramidal geometry in 3 and a distorted trigonal-bipyramidal geometry in 4. In 1 and 3, hmph is a bridging ligand that forms 1D and 2D coordination polymers, which are extended into 3D layers by hydrogen bonding and pi-pi interactions. (C) 2014 Elsevier Ltd. All rights reserved.
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    The syntheses, crystal structures, spectroscopic and thermal characterization of new pyridine-2,5-dicarboxylate compounds
    (Pergamon-Elsevier Science Ltd, 2015) Dogan, Deniz; Colak, Alper Tolga; Sahin, Onur; Tunc, Tuncay; Celik, Omer
    In this study, four new M(II)-isocinchomeronic acid (pyridine-2,5-dicarboxylic acid) complexes with ethylenediamine (en) and 2,2'-bipyridine (bipy), namely [Co(en)(3)][Co(pydc)(2)(H2O)(2)]center dot 2H(2)O (1), [Ni(Hpydc)(2) (H2O)2] (2), [Cu(en)(2)(H2O)][Cu-3(Pydc)(4)(en)(2)(H2O)(2)]center dot 3H(2)O (3) and [Cu(bipy)(3)][Cu(pydc)(bipy)(2)]center dot 2Cl center dot 12H(2)O (4) (H(2)pydc = pyridine-2,5-dicarboxylic acid), have been synthesised. Elemental, thermal analyses and IR spectroscopic studies have been carried out in order to characterise the complexes. The molecular structures of the complexes have been determined using single crystal X-ray diffraction. The geometry displayed by the Co(II) (1) and Ni(II) (2) ions is distorted octahedral. The Cu(II) ions display a square pyramidal geometry and distorted octahedral geometry in 3, while each Cu(II) ion exhibits a distorted octahedral geometry in 4. Molecules of each complex are linked into a 3D framework structure by N-H center dot center dot center dot O, O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds. (C) 2015 Elsevier Ltd. All rights reserved.