Synthesis and Crystal Structures of (E)-1-Phenyl-3-[(2,4,6-Trimethylphenyl)]prop-2-En-1-One and (E)-1-Phenyl-3-[(4-Trifluoromethylphenyl)]prop-2-En-1-One

Two chalcone compounds, namely (E)-1-phenyl-3-[(2,4,6-trimethylphenyl)]prop-2-en-1-one (1) and (E)-1-phenyl-3-[(4-trifluoromethylphenyl)]prop-2-en-1-one (2), have been synthesized and structurally characterized by elemental analysis, ¹H NMR spectrum, and single-crystal X-ray diffraction analysis. The chalcone molecules in (1) and (2) have the common skeleton of 1,3-diaryl-2-propen-1-one and adopt an (E)-configuration about the C = C double bonds. In addition, X-ray analysis reveals that the π···π stacking interactions are well observed in the crystal structure of (1) and (2).     

Synthesis,Crystal Structure,and DNA Binding Studies of the 3-(2-(2-Hydroxybenzylidene)Hydrazinyl)Quinoxalin-2(1H)-One

Crystallography Reports - The Schiff base, 3-(2-(2-hydroxybenzylidene)hydrazinyl)quinoxalin-2(1H)-one has been synthesized by condensation of 3-hydrazinyl quinoxalin-2(1H)-one and salicylaldehyde...     

The Reaction of (1,3,4-Oxadiazole-Thiolato) Mercury(II) with Triphenyl Phosphine

Crystallography Reports - The reaction of 5-phenyl-1,3,4-oxadiazole-2-thiol with mercury(II) acetate in ethanol led to the isolation of the complex [Hg(L)2] (1). Further reaction of 1 with a...     

Crystal Structure of 3,4-Dihydro-2-methoxy-2-methyl-4-phenyl-2H,5H-pyrano[3,2-c]chromen-2-one

Crystallography Reports - A new polymorph of 3,4-dihydro-2-methoxy-2-methyl-4-phenyl-2H,5H-pyrano[3,2-c]chromen-2-one (pyranocoumarin) was studied by X-ray diffraction. The crystallographic...     

Alternative Synthesis and Structural Analysis of the Antioxidant and Antitumor Agent 2-(3,5-Dimethoxyphenyl)-2,3-Dihydroquinolin-4(1H)-One

Journal of Chemical Crystallography - Herein we present the synthesis, structure and NMR and mass spectroscopic analyses of the antioxidant 2-(3,5-dimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one...     

Synthesis and Crystal Structure Analysis of 3,3'-[(3-Sulfanyl Phenyl)Methylene]Bis(4-Hydroxy-2H-1-Benzopyran-2-One) : 5-Methyl-1,3-Thiazol-2(3H)-Imine

Crystallography Reports - The structure of 3,3'-[(3-sulfanylphenyl)methylene]bis(4-hydroxy-2H-1-benzopyran-2-one) : 5-methyl-1,3-thiazol-2(3H)-imine was determined by X-ray crystallography. It...     

Synthesis and Molecular Structure of 2-(4-Chlorophenyl)-3-(phenyl-amino)-5-(thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one

Crystallography Reports - 2-(4-Chlorophenyl)-3-(phenylamino)-5-(thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one, C20H14N3OSCl was synthesized and its crystal structure was determined by...     

Crystal structure of 3-phenyl-7-bromoisoxazolo[4,5-d]pyridazin-4(5H)-one

The crystal and molecular structure of 3-phenyl-7-bromoisoxazolo[4,5-d]-pyridazin-4(5H-one, C₁₁H₆BrN₃O₂, has been determined from two- and three-dimensional X-ray data and refined by Fourier and least-squares methods toR = 0·101 for 1187 observed reflexions. Crystals of 3-phenyl-7-bromoisoxazolo-[4, 5-d]pyridazin-4(5H)-one are monoclinic:a = 7·67,b = 6·84,c = 20·52 Å, = 91·5 °,Z = 4, space groupP2₁/c. The benzene ring makes an angle of 4·5 ° with the plane of the isoxazole ring, and the other part of the molecule is slightly non-planar. The bond distances and angles compare well with those of other similar molecules. Two N-H...O hydrogen bonds join the two molecules related by a centre of symmetry. Close molecular packing is found in layers parallel to (100).     

Crystal Structure of 5-Butoxy-4-((3-butoxyphenyl)diazenyl)-3-methyl-1-phenyl-1H-pyrazole

Crystallography Reports - New azo-pyrazolone derivative, 5-butoxy-4-((3-butoxyphenyl) diazenyl)-3-methyl-1-phenyl-1H-pyrazole, C24H30N4O2, is synthesized, and its crystal structure is determined by...     

Structural investigation of five N-arylsulfonyloxazolidines

The crystal structures of (1R,5R,8S)-8-[(2R,4R)-4-ethyl-3-(2,4,6- trimethyl-benzenesulfonyl)-oxazolidin-2-yl]-1-hydroxy-bicyclo[3.3.1]nonan-3-one (1), formic acid (1S,2R)-2-{2-[(2R,4R)-4-ethyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexylidene}-1-trimethylsilanyl-ethyl ester (2), (2R,4R)-2-{(4S,5R,6S)-6-tertbutyl-2,2,4,5-tetramethyl-[1,3]dioxan-4-yl}-4-ethyl-3-(toluene-4-sulfonyl)-oxazolidine (3), (2S)-2-[(2R,4R,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-3,4-dihydro-2H-naphthalen-1-one (4) and (1R)-1-[(2R,4R,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-3,4-dihydro-1H-naphthalen-2-one (5) have been determined: (1) crystallizes in the orthorhombic space group P2₁2₁2₁ with cell dimensions a = 11.120(1), b = 13.809(1), c = 14.676(1) Å, (2) crystallizes in the monoclinic space group P2₁ with cell dimensions a = 12.577(3), b = 9.589(1), c = 13.971(3) Å, = 95.77(1) °, (3) crystallizes in the monoclinic space group P2₁ with cell dimensions a = 7.990(4), b = 11.282(9), c = 14.473(4) Å, = 96.31(3)°, (4) crystallizes in the orthorhombic space group P2₁2₁2₁ with cell dimensions a = 7.674(1), b = 14.647(1), c = 20.620(1) Å, (5) crystallizes in the monoclinic space group P2₁ with cell dimensions a = 7.890(2), b = 11.319(1), c = 13.493(3) Å, = 104.12(1)°.     

Crystal Structure and Computational Study of 5-Ethyl-4-(4-Methoxyphenethyl)-4,5-Dihydro-3H-1,2,4-Triazol-3-One and 4-(4-Methoxyphenethyl)-5-Propyl-4,5-Dihydro-3H-1,2,4-Triazol-3-One

Crystallography Reports - Molecular structures of compounds 5-ethyl-4-(4-methoxyphenethyl)-4,5-dihydro-3H-1,2,4-triazol-3-one, (C13H17N3O2) (I) and...     

4-(2-Methylphenyl)-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione (I) and 4-(4chlorophenyl)-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione (II)

The crystal and molecular structures of the title compounds have been determined by x-ray structure analysis. The compounds (I) and (II) crystallize in space groups P2₁2₁2₁ and 12/a respectively. The structures were solved by direct methods and refined to R = 0.058 and R = 0.046. The saturated pyrimidine-2-one ring in both structures deviates from the planarity. There are two intermolecular hydrogen bonds in (I) and (II). The configuration at C4 in (I) is S.     

Laser Raman Investigation of Solid State Rearrangement of bis(O-lodobenzoyl) peroxide into 1-(2'-Iodobenzoyloxy)-1, 2-benziodoxolin-3-one

In solid state, the thermal rearrangement of bis(O-iodobenzoyl) peroxide which yields 1-(2'-iodobenzoyloxy)-1,2-benziodoxolin-3-one,is investigated by laser Raman spectroscopy. The intramolecular vibration spectra are used to characterize this chemical rearrangement. The phonon spectra obtained as a function of the rearrangement progress show that, in spite of the reported topotactic nature of the reaction, it proceeds by a heterogeneous mechanism. A temperature dependence study of the phonon spectra reveal no mode-softening for any optical phonons. Therefore, no evidence has been found for this reaction to be phonon-assisted.     

Crystal structure of (E)-5-hydroxypyrrolizidin-3-one and (Z)-5-thioketalpyrrolizidin-3-one

The crystal structures of (E)-5-hydroxypyrrolizidin-3-one (2) and (Z)-5-thioketalpyrrolizidin-3-one (3) have been determined by single-crystal x-ray diffraction techniques and refined by full-matrix least squares. Molecule2 crystallizes in the monoclinic space groupP2₁/a(No. 14) witha=7.887(3) Å,b=9.788(5) Å,c=9.316(4) Å,=100.6(1), andZ=4. Molecule 3 crystallizes in the monoclinic space groupP2₁/c witha=12.947(14) Å,b=10.553(14) Å,c=9.629(14) Å,=101.4(1), andZ=4. The calculated density for both molecules is 1.33 g cm^–1. FinalR-factors were 5.1% for2 and 8.59% for3. The x-ray results showed that a change in configuration occurred in the reaction going from2 to3.     

4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl), 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl), and 4-(2,3,5-trichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl): conformational observations in the crystalline state

Hydrogen bonding interactions displayed by three crystalline chloro-substituted 4-phenyl-1,4-dihydropyridine molecules 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl), 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis (methoxycarbonyl) and 4-(2,3,5-trichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis (methoxycarbonyl), suggests that, in contrast to previous observation, sp orientation of the 3 or 5 substituted carbonyl group accomodates hydrogen bonding to the carbonyl oxygen atom when polar orthosubstituents exist on the phenyl ring.     

Synthesis and Crystal Structure of Compound 1-Phenyl-2-(1H-1,2,4-triazolo-yl)-3-phenyl-propen-1-one and 1-Diphenyl-3-(1,2,4-triazolo-yl)-1H,4H-1,5-benzothiazepine

Abstract  

The crystal structures of the compounds 1-phenyl-2-(1H-1,2,4-triazolo-yl)-3-phenyl-propen-1-one (2), and 2,4-diphenyl-3-(1,2,4-triazolo-yl)-1H,4H-1,5-benzothiazepine (3) were obtained by single crystal X-ray diffraction. Compound 2 crystallizes in the triclinic system with space group P − 1, a = 8.5553(17) ?, b = 9.6229(19) ?, c = 9.924(2) ?, α = 106.16(3)°, β = 108.03(3)°, γ = 105.14(3)°, V = 690.1(2) ?³, Z = 2. The compound 3 crystallizes in the orthorhombic system with space group Pbca, a = 12.904(3) ?, b = 15.864(3) ?, c = 19.140(4) ?, α = 90°, β = 90°, γ = 90°, V = 3918.3(14) ?³, Z = 8. H-bonds and π–π stacking are the main non-bonding interactions in the molecular structure. Details of the synthesis, structures, and spectroscopic properties of the two compounds are discussed.     

The crystal structure of 1-phenyl-3-methyl-4(salicylaldehyde hydrazone)-propenylidene-5-pyrazolone

The crystal structure of 1-phenyl-3-methyl-4-(salicylaldehyde hydrazone)-propenylidene-5-pyrazolone (PMPP-SH) was characterized by the single-crystal X-ray diffraction method. The cell parameters of PMPP-SH in the monoclinic P2₁/c space group are a = 10.851(1) Å, b = 11.679 (1) Å, c = 14.043 (2) Å and β = 91.89 (1)^∘. Analyzing the molecular structure suggest that, in the solid state, the title compound exists mainly in enaminopyrazolone form, which is stabilized by intramolecular hydrogen bonding, rather than NH-form.     

The synthesis and crystal structure of 2-[4(S)-4,5-dihydro-4-phenyl-2-oxazolinyl]-benzenamine, and 2-[4(S)-4,5-dihydro-4-benzyl-2-oxazolinyl]-benzenamine

Two oxazolines compound 1a and 1b, 2-[4(S)-4,5-dihydro-4-phenyl-2-ozazolinyl-benzenamine, and (C₁₅H₁₄N₂O), 2-[4(S)-4,5-dihydro-4-benzyl-2-ozazolinyl-benzenamine (C₁₆H₁₆N₂O) were obtained in moderate yield from the reactions of 2-aminobenzonitrile with optically active L-(+)-Phenylglycinol and L-(+)-Phenylalaninol, respectively, in chlorobenzene under dry, anaerobic conditions. ZnCl₂ was dried under vacuum and acted as a Lewis acid catalyst in this reaction. The structures of 1a and 1b were determined by X-ray diffraction and NMR. There exist intra- and intermolecular N-H…N hydrogen bonds in the crystal structure.     

Synthesis, Molecular Structure and Antioxidant Activity of (E)-4-[Benzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, a Schiff Base Ligand of 4-Aminoantipyrine

Abstract  

In this study, the title compound, C₁₈H₁₇N₃O (M _r = 291.35), was synthesized by the condensation reaction of 4-amino-1,5-dimethyl-2-phenylpyrazole-3-one and benzaldehyde. Single-crystal X-ray diffraction data revealed that this compound adopts a trans configuration around the central C=N double bond. It crystallizes in the monoclinic, space group P2₁/c with a = 12.9236(17) ?, b = 6.8349(9) ?, c = 17.072(2) ?, β = 90.316(3)°, V = 1508.0(3) ?³, Z = 4, D _c = 1.283 Mg/m³, F(000) = 616, μ = 0.082 mm⁻¹, R = 0.0442, and wR = 0.0936. Two different planes exist within the molecule; e.g. the pyrazolone and benzylidene groups attached to C9 of the pyrazolone ring are almost coplanar, whereas the phenyl group attached to the N1 of the pyrazolone ring is in another plane. Density functional theory (DFT) and time-dependent DFT calculations were performed to predict the electronic structure and absorption spectra of (E)-4-[benzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, a schiff base ligand of 4-aminoantipyrine using B3LYP/6-311G basis set on the AM1 optimized geometry. The predicted vibrational frequencies using the B3LYP/6-311G method were in strong agreement with the experimental IR spectra. The time dependent DFT calculations were used to evaluate the electronic absorption spectrum and three electron transition bands, which were mainly derived from the contribution of n → π* and π → π* transitions, were observed in both the experimental and predicted UV–Vis spectra. A maximum emission band at 370 nm was observed in the fluorescence spectra of the title compound. In addition, the title compound showed good DPPH antioxidant activity.     

2-(1-Methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one: Acid-catalyzed isomerization of the Z isomer to the E isomer

Crystals of (Z)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one (I) were obtained from a condensation reaction of 1-methyl-1H-indole-3-carboxaldehyde with 1-aza-bicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The isomeric (E)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one hydrochloride (II) was obtained by treating a methanolic solution of I with a 1M solution of hydrogen chloride diethyl ether, followed by crystallization of resultant product from methanol. Crystal data: I, is monoclinic, P2₁, a = 5.7440(10), b = 11.102(2), c = 10.708(2) Å, = 91.751(10)°, and V = 682.5(2) ų with Z = 2, for D _cal= 1.296 mg/m³ and II, is monoclinic, P2₁/c, a = 8.8510(2), b = 17.4990(5), c = 20.4300(5) Å, = 101.3620(12)°, V = 3102.26(14) with Z = 8, for D _cal= 1.316 mg/m³.