Synthesis,Characterization and Antibacterial Activity of <Emphasis Type="Italic">N</Emphasis>-(<Emphasis Type="Italic">N</Emphasis>-Acetic Acid-yl-Phthalimide-5-yl) Maleamic Acid Dihydrate

Abstract  

The compound N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid (C₁₄H₁₀N₂O₇, M _r  = 318) was synthesized and its structure was characterized by elemental analysis, ¹H NMR and IR spectra. The single crystal of the title compound (C₁₄H₁₄N₂O₉, M _r  = 354.27) was cultured and its structure was determined by single crystal X-ray diffraction. The crystal belongs to monoclinic system, space group P21/c with a = 14.3859(19), b = 12.5835(18), c = 8.6934(15) ?, β = 102.824(2)°, V = 1534.5(4) ?³, Z = 4, D _c  = 1.534 g cm⁻³, μ(Mo Kα) = 0.131 mm⁻¹, F(000) = 736. The final refinement gave R = 0.0652, wR(F ²) = 0.1239 for 2,703 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the asymmetric unit of the title compound contains one N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid molecule and two water molecules. One of the two water molecules is disordered. The phthalimide group is essentially planar. The crystal structure of the title compound is stabilized by N–H…O and O–H…O hydrogen bonds interactions. The compound N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid possesses moderate antibacterial activity.     

Synthesis and Crystal Structure of (5-Methyl-3-phenyl-1<Emphasis Type="Italic">H</Emphasis>-pyrazol-1-yl)-[5-(<Emphasis Type="Italic">p</Emphasis>-tolylamino)-2<Emphasis Type="Italic">H</Emphasis>-1,2,3-triazol-4-yl]methanone

Abstract  

(5-Methyl-3-phenyl-1H-pyrazol-1-yl)-[5-(p-tolylamino)-2H-1,2,3-triazol-4-yl]methanone was synthesized and characterized by ¹H NMR, MS and IR spectra data. The structure of title compound was identified by X-ray diffraction. Compound, C₂₀H₁₈N₆O, Mr = 358.40, crystallizes in the triclinic space group P-1 with unit cell parameters a = 10.303(6), b = 12.489(7), c = 15.305(9) ?, α = 108.489(12), β = 101.920(11), γ = 96.971(13)°, V = 1790.0(17) ?³, Z = 4, Dx = 1.330 mg/cm³. The final R was 0.0520.     

Synthesis and Crystal Structure of (<Emphasis Type="Italic">S</Emphasis>)-2-((<Emphasis Type="Italic">S</Emphasis>)-2-(<Emphasis Type="Italic">N</Emphasis>-Ts-Amino)-3-methylbutanoyl)-3-(1H-indol-3-yl)-6-phenyl-3,4-dihydro-1,2,4-triazin-5(2H)-one

Abstract  

The diastereoselective synthesis, NMR and X-ray structure of (S)-2-((S)-2-(N-Ts-amino)-3-methylbutanoyl)-3-(1H-indol-3-yl)-6-phenyl-3,4-dihydro-1,2,4-triazin-5(2H)-one—a potential antivirus agent are reported. The compound crystallizes in the triclinic space group P1 with unit cell parameters: a = 5.9259(6) ?, b = 9.6370(12) ?, c = 12.9541(9) ?, α = 109.210(9)°, β = 90.804(7)°, γ = 105.074(10)° and Z = 1.     

Spectroscopic Studies and Crystal Structure of (<Emphasis Type="Italic">Z</Emphasis>)-6-[(2-hydroxyphenylamino)methylene]-2-methoxycyclohexa-2,4-dienone

Abstract  The Schiff base (Z)-6-[(2-hydroxyphenylamino)methylene]-2-methoxycyclohexa-2,4-dienone has been synthesized from the reaction of 2-aminophenol with 2-hydroxy-3-methoxybenzaldehyde. The title compound has been characterized by elemental analysis, FT-IR, ¹H-NMR, ¹³C-NMR and UV–Visible techniques. The structure of the title compound also was determined crystallographically. The crystal structure has been solved by direct methods and refined by full-matrix least squares. The title compound crystallize in the monoclinic space group P2₁/c with a = 10.438(1), b = 8.851(1), c = 12.746(1) ?, β = 95.72(1)°, V = 1171.7(2) ?³, D _x  = 1.379 g cm⁻³, respectively (R1 = 0.0522 and wR2 = 0.126 for 1442 reflections [I > 2σ(I)]). Index Abstract   N-salicylideneaniline derivatives have been shown to exist as tautomeric forms due to intramolecular proton shifts between the phenol-oxygen and the imine-nitrogen, via intramolecular hydrogen bonding O–H···N or O···H–N.      

Synthesis and Crystal Structure Determination of 3-Phenyl-2-(2-phenylhydrazino)-4<Emphasis Type="Italic">H</Emphasis>-1-benzothiopyran-4-one

Abstract  

A new type of substituted benzothiopyranone, 3-phenyl-2-(2-phenylhydrazino)-4H-1-benzothiopyran-4-one, has been prepared by the condensation-acid cyclization of polylithiated phenylacetic acid phenylhydrazide with lithiated methyl thiosalicylate. Absorption spectra, especially ¹³C NMR, provided good indication of its structure, which was conclusively established with X-ray crystal structure analysis. In comparison to the few benzothiopyran X-ray reports documented, the benzothiopyranone ring of the molecule was found to be essentially planar, with the 3-phenyl ring nearly perpendicular to the benzothiopyranone fused-ring system. Crystals of C₂₁H₁₆N₂OS are orthorhombic, P2₁2₁2₁, a = 10.140(4) ?, b = 10.432(4) ?, c = 16.228(7) ?, Z = 4, V = 1717(1) ?³, R ₁ = 0.0267 and wR ₂ = 0.0725 for reflections with I > 2σ(I). The molecular packing in the crystal is the result of N–H···O hydrogen bonding.     

Synthesis,Crystal Structure and Thermal Properties of <Emphasis Type="Italic">N</Emphasis>-Acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline and <Emphasis Type="Italic">N</Emphasis>-Acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline

Abstract  

Two novel ferrocenyl substituted N-acetyl-2-pyrazolines, N-acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline (3) and N-acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline (4), have been synthesized and characterized by FTIR, ¹H-NMR, ¹³C-NMR techniques, elemental analysis and X-ray structure analysis. Thermal properties of these compounds have been determined by TGA, DTA and DSC analysis. Compound 3 (C₁₉H₁₈N₂O₂Fe) crystallizes in the monoclinic space group P21/c and Z = 4, with a = 8.6970(4) ?, b = 18.4725(9) ?, c = 11.0041(5) ?, β = 110.942(3)°. Compound 4 (C₁₉H₁₈N₂OSFe) crystallizes in the orthorhombic space group Fdd2 and Z = 16, with a = 84.242(2) ?, b = 13.5416(5) ?, c = 5.9405(2) ?, β = 90°. In terms of crystal packing, each compound shows different molecular arrangement, which are stabilized by C–H···O intermolecular weak hydrogen bonds, and/or C–H···π interactions.     

Crystal Structure and Conformational Analysis of 4-[(<Emphasis Type="Italic">p</Emphasis>-<Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">N</Emphasis>-Dimethylamino)Benzylidene]-2-Phenyloxazole-5-One

Abstract  

Molecular and crystal structure of 4-[(p-N,N-dimethylamino)benzylidene]-2-phenyloxazol-5-one, C₁₈H₁₆N₂O₂, have been determined by single crystal X-ray diffraction study. The title compound is monoclinic, with a = 12.1704(23) ?, b = 3.9810(5) ?, c = 30.9603(56) ?, β = 101.176(15)°, Z = 4, D _x = 1.32 g/cm³, μ(Mo Kα) = 0.087 mm⁻¹, and space group is P12₁/c1. The structure was solved by direct methods and refined to a final R = 0.047 for 3166 reflections with I > 2σ(I). The crystal structure is stabilized by C–H⋯O and C–H⋯N type intra-molecular, C–H⋯O type inter-molecular interactions. To enlighten the flexibility and the geometric isomerism (E or Z) of the title compound, the selected torsion angle is varied from −180 to 180° in every 10° separately and molecular energy profile is calculated and analyzed.     

Synthesis and the Crystal Structure of (<Emphasis Type="Italic">E</Emphasis>)-2-(7-(3-(Thiophen-2-yl)acrylamido)-2,3-dihydro-5-oxobenzo[e][1,4]oxazepin-1(5H)-yl)ethyl acetate

Abstract  

Details of the synthesis and crystal structure determination of (E)-2-(7-(3-(thiophen-2-yl)acrylamido)-2,3-dihydro-5-oxobenzo[e][1,4]oxazepin-1(5H)-yl)ethyl acetate are presented. The compound crystallizes in the triclinic P−1 space group (a = 8.3377(17), b = 9.792(2), c = 12.469(3) ?, α = 96.39(3)°, β = 108.50(3)°, γ = 97.68(3)°, V = 943.9(3) ?³, Z = 2). Interesting features of the structure include intermolecular hydrogen bonding between the amide proton on one molecule and the carbonyl oxygen of the dihydrooxazepinone ring on an adjacent molecule, the boat conformation of the dihydrooxazepinone ring, and π-π stacking between thiophene and phenyl rings on adjacent molecules with a distance between centroids of 3.79(2) ?.     

Crystal Structure of 4-Bromo-3,4-Dichloro-1-(1-Morpholinyl)-1-(Decylsulfanyl)-2-Nitro-Buta-1,3-Diene

Abstract  

The compound 4-bromo-3,4-dichloro-1-(1-morpholinyl)-1-(decylsulfanyl)-2-nitro-buta-1,3-diene was synthesized from the reaction of 4-bromo-1,3,4-trichloro-1-(decylsulfanyl)-2-nitro-buta-1,3-diene with morpholine and characterized by elemental analysis, IR spectrum, UV spectra, ¹H NMR,¹³C NMR and X-ray single crystal determination. In the title compound, C₁₈H₂₉BrCl₂N₂O₃S, crystallizes in the monoclinic space group P2₁/c, a = 15.8326(4) Å, b = 8.9915(10) Å, c = 16.7528(5) Å, β = 100.808(10)°, V = 2,342.6(3) Å³, Z = 4, R ₁ = 0.0590 and wR ₂ = 0.0940. The morpholine ring adopts a chair conformation. The morpholine ring and the butadiene group are inclined at an angle of 113.4 (1)°. The butadiene unit is not planar as can be expected if the two double bonds are fully conjugated.     

The Synthesis and Crystal Structure Determination of Phenyl 2-(3,4-dihydro-1(2<Emphasis Type="Italic">H</Emphasis>)naphthalenylidine)hydrazinecarboxylate and Phenyl (2,4-dichlorophenyl-methylene)hydrazinecarboxylate

Abstract  

(E)-Phenyl 2-(3,4-dihydro-1(2H)-naphthalenylidine)hydrazinecarboxylate and (E)-phenyl (2,4-dichlorophenylmethylene)hydrazinecarboxylate were prepared by the condensation of 1-tetralone or 2,4-dichlorobenzaldehyde with phenyl hydrazinecarboxylate. Crystals of C₁₇H₁₆N₂O₂ 3 are monoclinic, C2/c, a = 17.763(4) ?, b = 8.353(2) ?, c = 40.233(8) ?, Z = 16, V = 5,839(2) ?³, R ₁ = 0.0448 and wR ₂ = 0.1104 for reflections with I > 2σ(I). Crystals of C₁₄H₁₀N₂O₂Cl₂ 5 are orthorhombic, P2₁2₁2₁, a = 8.288(3) ?, b = 14.082(2) ?, c = 23.788(5) ?, Z = 8, V = 2,777(1) ?³, R ₁ = 0.0815 and wR ₂ = 0.2006 for reflections with I > 2σ(I). The molecular packing in the crystal for both compounds is the result of N–H···O hydrogen bonding.     

Synthesis and Crystal Structure of a New Schiff Base 4-[(2-hydroxy-benzylidene)-amino]-<Emphasis Type="Italic">N</Emphasis>-(5-methyl-isoxazol-3-yl)-benzenesulfonamide

Abstract  The structure of the title compound (C₁₇H₁₅N₃O₄S)₂ the schiff base, bis(N-(5-methyl-3-isoxazolyl)-4-[(2-hydroxy benzylidene)-amino]) benzene sulfonamide was elucidated by H¹, C¹³ NMR, UV–VIS and IR spectroscopic techniques. The X-ray structure was determined in order to establish the conformation of the molecule. The compound crystallizes in the triclinic space group P-1, with a = 11.419(1), b = 11.426(0), c = 13.316(1) ?, α = 71.94(2), β = 89.79(1), γ = 89.14(2)° and Z = 4. Two benzene rings and azomethine group are practically coplanar, as a result of intramolecular hydrogen bonds involving the hydroxy O atom and azomethine N atom. The component species further interact via N–H···N and C–H···O hydrogen bonds and π–π stacking interactions. Index Abstract  The title compound (C₁₇H₁₅N₃O₄S)₂, Schiff base, bis(N-(5-methyl-3-isoxazolyl)-4-[(2-hydroxy benzylidene)-amino]) benzene sulfonamide was synthesized by the condensation of 4-amino-N-(5-methyl-3-isoxazolyl) benzene sulfonamide (SMZ) and 2-hydroxy benzaldehyde (SA). Its structure was confirmed by single crystal X-ray diffraction analysis. Electronic supplementary material  The online version of this article (doi:) contains supplementary material, which is available to authorized users.     

The Synthesis and Structure of Two Novel <Emphasis Type="Italic">N</Emphasis>-(Benzothiazol-2-yl)benzamides

Abstract  Two novel benzothiazoles 2-chloro-N-(benzothiazol-2-yl)benzamide (1) and 2-chloro-N-(6-cyanobenzothiazol-2-yl)benzamide (2) were obtained in multistep synthesis. They were characterised by means of IR, ¹H- and ¹³C-NMR spectroscopy and also by single-crystal X-ray diffraction. The compound 1 crystallises with triclinic space group P , a = 9.5923(8) ?, b = 9.8583(8) ?, c = 13.8962(10) ?, α = 89.162(6)°, β = 77.741(7)°, γ = 80.064(7)°, V = 1264.5(2) ?³, Z = 4 and compound 2 crystallises as methanol solvate with monoclinic space group P 2₁/n, a = 7.5093(9) ?, b = 13.0211(14) ?, c = 16.032(2) ?, β = 92.717(10)°, V = 1565.9(3) ?³, Z = 4. Both crystal structures consist of discrete dimers connected into a three-dimensional network by intermolecular C–H···O and C–H···X (X = Cl or S) hydrogen bonds and by face-to-face π–π stacking interactions. Index Abstract  The synthesis and structure of two novel N-(benzothiazol-2-yl)benzamides. Irena Ćaleta, Dominik Cinčić, GraceKarminski-Zamola and Branko Kaitner. Hydrogen bonds and π–π interactions in N-(benzothiazol-2-yl)benzamides N-(benzothiazol-2-yl)benzamides.      

An X-Ray Crystallographic Study of Five Compounds from a Series of 1,x-<Emphasis Type="Italic">bis</Emphasis>-(4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)alkanes

Abstract  

The crystal structures of a series of bis-(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)alkanes, compounds 5 to 9, have been determined by single crystal X-ray diffraction analysis. The structural parameters of the triazinone rings in the five compounds do not display systematic differences with respect to those reported for a few analogous compounds. The benzotriazinone rings in 5 and 9 are almost perpendicular to the alkylic chain. The molecules in the crystal packing are linked by means of a weak C–H···X H-bond (X = N/O). Compound 6 has two independent molecules in the asymmetric unit; one of the molecules displays disorder within the benzotriazinone moiety linked in position 1 to the propane alkylic group. The disordered molecule displays two conformations of the benzotriazinone linked in position 1 to the propane bridge. Compound 8 also displays disorder within the benzotriazinone moiety linked in position 1 to the pentane alkylic spacer group. The molecules of compound 7, in the crystal packing, also form intra and inter-molecular C–H···X (X = N/O) hydrogen bonds. None of these compounds show any tendency to adopt a folded conformation with intramolecular π–π stacking between benzotriazinone units. Crystal data: 5 C₁₆H₁₂N₆O_2, monoclinic, space group P2 ₁ /c, a = 4.8370(2)?, b = 14.7845(7)?, c = 10.0837(4)?, β = 95.430(2)°, V = 717.88(6)?³, for Ζ = 2; 6 C₁₇H₁₄N₆O_2, triclinic, space group P-1, a = 7.4237(4)?, b = 14.4738(9)?, c = 15.0359(10)?, α = 91.871(3)°, β = 92.147(3)°, γ = 101.233(3)°, V = 1582.2(2)?³, for Ζ = 4; 7 C₁₈H₁₆N₆O_2, monoclinic, space group C2/c, a = 33.8886(10)?, b = 6.4593(2)?, c = 16.0608(6)?, β = 102.298(1)°, V = 3435.0(2)?³, for Ζ = 8; 8 C₁₉H₁₈N₆O_2, triclinic, space group P-1, a = 7.2592(2)?, b = 7.6795(2)?, c = 16.1003(5)?, α = 85.292(1)°, β = 81.367(1)°, γ = 88.377(1)°, V = 884.26(4)?³, for Ζ = 2; 9 C₂₀H₂₀N₆O_2, monoclinic, space group P2 ₁ /c, a = 7.2668(2)?, b = 4.5612(1)?, c = 28.1993(12)?, β = 97.313(2)°, V = 927.07(5)?³, for Ζ = 2.     

Spectroscopic Studies and Structure of 4-(3-Benzoylthioureido)benzoic Acid

Abstract  

4-(3-Benzoylthioureido)benzoic acid has been synthesized from the reaction of 4-aminobenzoic acid with benzoyl isothiocyanate. The title compound has been characterized by elemental analysis, MS, FT-IR, ¹H-NMR, ¹³C-NMR and UV–Visible techniques. The structure of the compound has also been examined crystallographically. The title compound crystallizes in the triclinic space group P-1 with a = 3.969(1), b = 13.039(1), c = 13.504(1) ?, α = 96.50(1)°, β = 92.25(1)°, γ = 94.94(1), V = 691.0(1) ?³ and D _x  = 1.444 g cm⁻³, respectively. The crystal structure has been solved by direct methods and refined by full-matrix least squares and found R ₁ = 0.031 and wR ₂ = 0.081 for 2909 observed reflections [I > 2σ(I)].     

Synthesis,Characterization and Antibacterial Activity of <Emphasis Type="Italic">N</Emphasis>-(2,3,4-Trimethoxy-6-methylbenzylidene)-2-methyl-benzenamine

Abstract  The title compound N-(2,3,4-trimethoxy-6-methylbenzylidene)-2-methyl-benzenamine (C₁₈H₂₁NO₃, M _r = 299.36) was synthesized and characterized by elemental analysis, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P2₁/n, with a = 7.2804(5), b = 8.5909(9), c = 26.117(3) ?, β = 92.056(2)°, V = 1,632.4(3) ?³, Z = 4, D _c = 1.218 g cm⁻³, λ = 0.71073 ?, μ(Mo Kα) = 0.083 mm⁻¹, F(000) = 640. The final refinement gave R = 0.0497, wR(F ²) = 0.1157 for 2,879 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the dihedral angle between the two phenyl rings is 25.9 (2)°. The molecule adopts a trans configuration about the central C=N functional bond. The crystal structure is stabilized by C–H…O hydrogen bonds and π–π stacking interactions. The title compound possesses moderate antibacterial activity. Graphical Abstract  The title compound N-(2,3,4-trimethoxy-6-methylbenzylidene)-2-methyl-benzenamine (C₁₈H₂₁NO₃, M _r = 299.36) was synthesized and characterized by elemental analysis, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P2₁/n, with a = 7.2804(5), b = 8.5909(9), c = 26.117(3) ?, β = 92.056(2)°, V = 1,632.4(3) ?³, Z = 4, D _c = 1.218 g cm⁻³, λ = 0.71073 ?, μ(Mo Kα) = 0.083 mm⁻¹, F(000) = 640. The final refinement gave R = 0.0497, wR(F ²) = 0.1157 for 2,879 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the dihedral angle between the two phenyl rings is 25.9 (2)°. The molecule adopts a trans configuration about the central C=N functional bond. The crystal structure is stabilized by C–H…O hydrogen bonds and π–π stacking interactions. The title compound possesses moderate antibacterial activity.      

Synthesis,Structure, and Two Polymorphs of 4-((1,3-Dioxoisoindolin-2-yl)methyl)-1-methoxypyridinium tetrafluoroborate

Abstract  

4-((1,3-Dioxoisoindolin-2-yl)methyl)-1-methoxypyridinium tetrafluoroborate, C₁₅H₁₃BF₄N₂O₃, 1, was obtained by alkylation of the corresponding N-oxide and has been characterized by ¹H and ¹³C NMR, IR, UV spectroscopy and by X-ray crystallography. The crystal undergoes a reversible phase transition between 173 and 293 K. At room temperature, crystals are orthorhombic, space group Pna2₁ with a = 7.2487(3) ?, b = 17.8359 (8) ?, c = 12.4077(6) ?, V = 1604.16(12) ?³, and Z = 4. At 173 K, cations adopt four conformations in monoclinic space group Cc with a = 24.7076(29) ?, b = 14.4145(9) ?, c = 21.8765(25) ?, β = 126.249(17)°, V = 6283.3(7) ?³, and Z = 16. The compound is photostable in the crystal and does not undergo homolytic N–O bond cleavage as observed in solution.     

The Synthesis and Crystal Structure of New Bis(3-chlorophenyl)-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-methanol

Abstract  The title compound bis(3-chlorophenyl)-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-methanol 8 has been synthesized and established by H NMR, IR and MS spectra and X-ray diffraction crystallography. Compound 8, C₂₃H₂₉Cl₂N₃O, Mr = 424.31, crystallizes in the monoclinic space group P2₁/c with unit cell parameters a = 14.5402(6) ?, b = 12.5888(5) ?, c = 11.6510(5) ?, α = 90o, β = 100.183o(2), γ = 90o, V = 2099.05(15) ?³, D_x = 1.343 mg m⁻³ and Z = 4. The final R was 0.0514. The molecular conformation and packing is stabilized by interactions of intermolecular O1–H1···N3′. Index Abstract  The structure of bis(3-chlorophenyl)-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-methanol by the reaction of compound 4 and Grignard regent is studied.      

Synthesis and Crystal Structure of 3-Methyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole

Abstract  

The title compound, 3-methyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole was synthesized by reaction of diphenylphosphazoanilide with N-acetyl-N′-(2-pyridoyl)hydrazine. Crystals suitable for X-ray analysis were obtained from a mixed solution of water and ethanol in a one-to-one volume ratio. The crystal is orthorhombic, space group P2₁2₁2₁ with crystallographic parameters: a = 19.414(4) Å, b = 17.172(3) Å, c = 7.4850(15) Å, β = 90.00°, μ = 0.079 mm⁻¹, V = 2495.3(8) Å³, Z = 8, Dc = 1.258 g/cm³, F(000) = 992, T = 295(2) K. The X-ray results showed that in the crystal structure of the title compound, the 1,2,4-triazole, pyridine and benzene rings are not coplanar.     

Synthesis and Structure of 9-Bromo-2-fluoro-8-[ethyl, (E)-2-propenoate-3-yl]-6,7-dihydro-5H-benzocycloheptene

Abstract  

This paper reports a synthesis of 9-bromo, 2-fluoro substituted, and Z-ring locked (by a trimethylene bridge at C8 and C11) crystalline fluorine substituted bicyclic ring-fused polyene bearing a δ-bromo-α,β,γ,δ-unsaturated ester unit. It is a structural element found in sterically hindered retinoids and is a useful advanced intermediate in the total synthesis of these naturally occurring bioactive polyenes. The synthon, 8-fluoro-1-benzosuberone was converted into 9-bromo-2-fluoro-6,7-dihydro-5H-benzocycloheptene-8-carboxaldehyde chemoselectively and regioselectively and then into 9-bromo-2-fluoro-8-[ethyl, (E)-2-propenoate-3-yl]-6,7-dihydro-5H-benzocycloheptene in a step economical and stereoselective manner by treatment with triethylphosphonoacetate and NaH in THF. The process creates a new carbon–carbon double bond between C12 and C13 and produces a previously unreported product that has been characterized by X-ray, IR, ¹H NMR, ¹³C NMR, GC–MS, and elemental analysis. Crystals are triclinic, space group P-1, a = 7.581(2), b = 8.324(2), c = 11.759(3) ?, α = 96.723(17), β = 96.056(16), γ = 101.999(17)°, Z = 2.     

Synthesis and Crystal Structure of a New Cobalt(II) Complex: Bis(pyridine)bis(4,4,4-trifluoro-1-(6-methoxynaphthalen-2-yl)butane-1,3-dione) Cobalt(II)

Abstract  

A new Co(II) complex 2 with ligand 4,4,4-trifluoro-1-(6-methoxynaphthalen-2-yl) butane-1,3-dione 1 and pyridine are prepared and crystallized from an acetone solution. The obtained red and transparent crystal conforms to the empirical formula of Co(C₁₅H₁₀O₃F₃)₂·(C₅H₅N)₂. It crystallizes in monoclinic, space group C2/c with a = 23.3152(14), b = 12.0225(7), c = 15.3950(10) ?, β = 124.1360(10)°, V = 3571.8(4) ?³, Z = 4, C₄₀H₃₀CoF₆N₂O₆, Mr = 807.59, F(000) = 1652, Dc = 1.502 g/cm³, μ = 0.564 mm⁻¹, the final R = 0.0466 and wR = 0.1043 for 3901 observed reflections with I > 2σ(I). X-ray structural analysis revealed that the Co(II) atom is coordinated by two oxygen atoms of 1,3-dione ligands 1 and two nitrogen atoms of pyridines, forming a distorted octahedron coordination geometry.