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

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 C22(14) chains. Compounds (III) and (IV) both form centrosymmetric R22(10) dimers built from N—H⋯O hydrogen bonds, while compound (V) forms a centrosymmetric R22(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

Structural Characterization of 6-Bromo-5-nitroquinoline-1-oxide: A Quantum Chemical Study and XRD Investigations

The chemical properties of recently synthesized 6-bromo-5-nitroquinoline-1-oxide under a mild reaction condition by regioselective nitration of 6-bromoquinoline-1-oxide at C5 on going our research were investigated as theoretical. The crystal structure of 6-bromo-5-nitroquinoline-1-oxide, C9H5BrN2O3, was determined by X-ray analysis. Crystallized in Pmc21 in the orthorhombic space group with a = 13.6694 (13) Å, b = 9.6036 (10) Å, c = 14.1177 (16) Å, Z = 8, Dx = 1.929 mg/m3. In this study, theoretical calculations were performed using the GaussView 4.1 molecular imaging program and the Gaussian03W packet program. In the ground state, stable structures of the wholes molecule in the gaseous phase are investigated based on Density Functional Theory (DFT). Molecularly optimized geometries, dipole moments, charge density, thermodynamic properties (heat capacity, enthalpy, entropy), chemical shift values (1H NMR and 13C NMR), energies, molecular electrostatic potentials and frontier orbitals (HOMO and LUMO) B3LYP/6-311G(d,p) base set. Thus, the results obtained by the X-ray diffraction method are supported by theoretical foundations. Finally, the distribution of interactions between molecules in the crystal structure of 6-bromo-5-nitroquinoline-1-oxide (3) was investigated by analysis using Hirshfeld surface production and two-dimensional fingerprinting

Crystal and Molecular Structure of N-Trityl-m-aminophenol Chloroform Solvate

The title compound, (C26H23N)3·CHCl3, was synthesized by the reaction of trityl bromide with m-toluidine in chloroform and crystalized in the trigonal R3 space group (Z = 6) with the one molecule of chloroform, and with a = 20.765(5), b = 20.765(5), c = 24.924(5)Å, α = β = 90°, γ = 120°, V = 9307(4)Å3, Z = 6 and Dx = 1.250 Mg m-3. A least-squares refinement gave a residual index of R = 0.065 for 3540 observed reflections. Three phenyl rings of the title compound are at angles of 60.39(13), 74.10(14) and 70.17(13)° to the six-membered ring of the planar aminophenol group. The dihedral angles between three phenyl rings are 73.60(16), 87.80(15) and 56.52(15)°

Synthesis, Spectral and Thermal Studies, and Crystal Structure of cis-Bis(4-methylimidazole)bis(picolinato)copper(II) [Cu(pic)2(4-MeIm)2]

The mixed-ligand picolinato (pic) complex of Cu(II) with 4-methylimidazole (4-MeIm),[Cu(pic) 2 (4-MeIm) 2], was synthesized and characterized by elemental analysis, magnetic susceptibility, spectroscopic methods (UV/vis and FT-IR) and X-ray diffraction. In the slightly distorted octahedral cis-bis(4-methylimidazole)bis(picolinato)copper(II) complex, the pic ligands are coordinated to the Cu(II) ion as bidentate N,O-donors forming chelate rings. The 4-MeIm ligands are N-coordinated in cis positions. The complex crystallizes in the triclinic space group P̄1 with unit cell parameters a=9.204(5), b=9.498(5),c=13.095(5)̊A, α=90.395(5), β=101.687(5), γ=112.291(5)◦andZ=2. ydrogen bondings and C-H···πinteractions occur between picolinato and methylimidazoleligands of eighboring complex molecules. The thermal decomposition of the complex is describe

Synthesis, Spectral and Thermal Studies, and Crystal Structure of cis-Bis(imidazole)bis(picolinato)copper(II) Dihydrate [Cu(pic)2(im)2]·2H2O

The mixed-ligand picolinato (pic) complex of Cu(II) with imidazole (im), [Cu(pic) 2(im)2]·2H2O, was synthesized and characterized by elemental analysis, magnetic susceptibility, spectral methods (UV/vis and FT-IR), simultaneous TG, DTA techniques, mass spectroscopy, and X-ray diffraction. The complex crystallizes in the monoclinic space group Cc with the following unit cell parameters:a=16.381(1),b=9.556(1),c=5.177(1)̊A,β=119.074(5)◦,Z=4. In the octahedral complex, the picolinato ligands are coordinated to the copper(II) ion as bidentate N,O-donors forming chelate rings. The imidazole ligands are N-coordinated at cis positions. The thermal decomposition pathway of the complex has been studied by the help of thermal analyses data (TG and DTA) and of the mass spectroscopic fragmentation pattern. The volatile products observed in the thermal decomposition process were also observed in the mass spectrometer ionisation process, except for the molecular peak, and it was concluded that the ionisation and thermal decomposition pathways of the complex resemble each other

6-Bromo-1,2,3,4-tetrahydroquinoline-8-carbonitrile

In the title compound, C10H9BrN2, one of the methylene groups of the piperidine ring is disordered over two sets of sites in a 0.692 (8):0.308 (8) ratio, which leads to two envelope conformations. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generate R22(12) loops

Crystal structure of racemic [(1R,2S,3R,4S,6S)-2,6-bis(furan-2-yl)-4-hydroxy-4-(thiophen-2-yl)cyclohexane-1,3-diyl]bis(thiophen-2-ylmethanone). Corrigendum

In the paper by Çelik et al. [Acta Cryst. (2016), E72, 976–979], the name and affiliation of one of the authors is incorrect

Crystal Structure of (1RS,2SR,3SR,4SR,9RS)-1,2,3,9-Tetrabromo-1,2,3,4-tetrahydro-1,4-methanonaphthalene

In the title compound, C11H8Br4, there is a norbornane skeleton with four Br atoms, having a benzene ring fused on one side. It crsytalizes in the orthorhombic Pbca space group. The unit-cell parameters at 294(2)K are a = 11.9910(10), b = 11.335(2), c = 18.191(4)Å, V = 2472.5(7)Å3, Dx = 2.470 g cm-3, Z = 8

(2Z)-2-(5-Fluoro-1-methyl-2-oxoindolin-3-ylidene)-N-(3-fluorophenyl)hydrazine-1-carbothioamide

In the title compound, C16H12F2N4OS, the whole molecule is essentially planar (r.m.s deviation = 0.003 Å), with only the H atoms of the methyl group lying out of the molecular plane. A planar indole fused-ring system (r.m.s deviation = 0.004 Å) is linked through a hydrazine–carbothioamide bridge to a fluorobenzene ring, with the indole ring system and inclined to the fluorobenzene ring by 4.26 (14)°. The planarity of the molecule is strengthened by three intramolecular N—H...N, N—H...O and C—H...S hydrogen bonds that generate S(5), S(6) and S(6) ring motifs, respectively. In the crystal, π–π stacking interactions combine with C—H...·F hydrogen bonds to link the molecules into layers parallel to the (10-1) plane