Synthesis and Crystal Structure of Bis(<Emphasis Type="Italic">N</Emphasis>-alkyl-<Emphasis Type="Italic">N</Emphasis>-phenyl dithiocarbamato)mercury(II)

Abstract  

The mixed ligand dithiocarbamate complex was synthesized by the reaction between the ammonium salt of the dithiocarbamate ligands with mercury salt. There are two mercury complexes in the asymmetric unit with a compositional disorder between an ethyl group and a methyl group. A distorted tetrahedral geometry is found for each mercury atom defined by four sulphur atoms derived from two asymmetrically chelating dithiocarbamate ligands. IR spectra show thioureide υ(C–N) bands at 1491 cm⁻¹ which is higher than observed in the simple complexes of the same ligands. The effect of alkyl substituents were observed in the magnetic unequivalence of the thioureide and phenyl units in the NMR spectroscopy. The molecules are related to each other by virtue of the compositional disorder which exists at three positions in the alkyl group across the unit. The compound crystallizes in the triclinic space group P-1 with a = 10.4764(10) ?, b = 11.0433(10) ?, c = 18.5566(17) ?, α = 97.8980(10)^°, β = 95.3340(10)^°, γ = 110.3010(10)^°, and Z = 2.     

Crystal Structure of Two <Emphasis Type="Italic">V</Emphasis>-shaped Ligands with <Emphasis Type="Italic">N</Emphasis>-Heterocycles

Two V-shaped ligands with N-heterocycles, bis(4-(1H-imidazol-1-yl) phenyl)methanone (1), and bis(4-(1H-benzo[d]imidazol-1-yl)phenyl)methanone (2) have been synthesized and characterized by elemental analyses, IR and 1H NMR spectroscopy. Crystal structures of 1 and 2 have been determined by X-ray diffraction. The crystal of 1 is monoclinic, sp. gr. P2₁/c, Z = 4. The crystal of 2 is orthorhombic, sp. gr. Fdd2, Z = 8. X-ray diffraction analyses show that the V-shaped angles of 1 and 2 are 122.72(15)° and 120.7(4)°, respectively. Intermolecular C–H···O, C–H···N, C–H···π, and π···π interactions link the components into three-dimensional networks in the crystal structures.     

Synthesis,Characterization and Crystal Structure of 2-Nitro-<Emphasis Type="Italic">N</Emphasis>-[2,4-dichlorophenyl]-<Emphasis Type="Italic">N</Emphasis>-(2-methylbenzoyl)benzamide

Abstract  

The title benzamide was synthesized in two steps by refluxing N-(2,4-dichlorophenyl)-2-nitrobenzamide with thionyl chloride in dry toluene to afford 2,4-dichloro-N-[chloro(2-nitrophenyl]methylene)benzenamine intermediate followed by treatment with 2-methyl benzoic acid in presence of triethyl amine. The structure was confirmed by spectroscopic and elemental analysis. The crystal structure was determined from single crystal X-ray diffraction data. It crystallizes in the monoclinic space group P 21/c with unit cell dimensions a = 10.4122(7), b = 12.9613(7) and c = 15.5518(10) ?. The dihedral angle between the two aromatic rings is 82.32(4)°. The N2 and N3 nitro groups are oriented with respect to their attached phenyl rings at dihedral angles of 1.97(3)° and 15.73(3)°, respectively.     

Structure of 6,13-bis(<Emphasis Type="Italic">N</Emphasis>, <Emphasis Type="Italic">N</Emphasis>-dimethylcarbamoyl) thioquinanthrene

The crystal structure of 6,13-bis-(N,N-dimethylcarbamoyl)thioquinanthrene 3 has been determined as monoclinic, with space group P2(1)/c with lattice parameters a = 10.044(2) Å, b = 21.385(4) Å, c = 10.889(3) Å, = 102.92(3)°, Z = 4 and D_calc = 1.342 Mg/m³. The middle 1,4-dithiin ring in the title compound 3, C₂₄H₂₀N₄O₂S₂ is in a boat conformation with the dihedral angle between the planes of the aromatic rings 132.45(8)°.     

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.     

A New <Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">N</Emphasis>-Dimethyl Purine from an Australian <Emphasis Type="Italic">Dictyoceratid Sponge</Emphasis>

Abstract  

N6-methyl mucronatine (C₈H₁₂N₅O) has been isolated from a dictyoceratid sponge collected in South East Queensland. The solid state structure of the new metabolite (I) was confirmed by X-ray crystallography, while an NMR study in d ₄-MeOH reveals the presence of a minor tautomer identified as (II).     

Crystal and Molecular Structures of Di-1-Adamantylthiophosphinic Chloride, <Emphasis Type="Italic">P</Emphasis>,<Emphasis Type="Italic">P</Emphasis>-Diphenyl-<Emphasis Type="Italic">N</Emphasis>-Benzyl Phosphinothioic- and Selenoic- Amides

Abstract  Synthesis and X-ray structural determination of three phosphorus compounds are reported. (3b) is monoclinic P2(1)/c with a = 11.852(1), b = 12.825(1), c = 12.445(1) ?, β = 103.693(1)o; (4a) and (4b) are monoclinic P2(1)/n with a = 12.1422(16), b = 9.0860(12), c = 14.845(2) ?, β = 96.498(3)o for (4a), and a = 12.2714(16), b = 9.2812(12), c = 14.800(2) ?, β = 97.176(2)o for (4b). They all exhibit distorted tetrahedral geometry about the P atom. Ph₂P(X)NHC₇H₇ (X=S (4a) and X=Se (4b)) show typical P–S and P–Se double bond distances and P–N single bonds, while P–S bond in 1-Ad₂P(S)Cl (3b) is comparable to P–S single bonded probably due to the largeness of 1-adamantyl groups. Graphical Abstract  Synthesis and X-ray structural determination of 1-Ad₂P(S)Cl (3b), Ph₂P(S)NHC₇H₇ (4a) and Ph₂P(Se)NHC₇H₇ (4b) are reported.      

Crystal and Molecular Structure of <Emphasis Type="Italic">N</Emphasis>-(Phenylthio)phthalimide

The title compound N-(Phenylthio)phthalimide has been synthesized and characterized by FT-IR, NMR, and X-ray single-crystal determination. The compound crystallizes in the triclinic sp. gr. \(P\bar 1\) with Z = 2. The title compound is not planar. The dihedral angle between the phthalimide and phenyl ring systems is 77.41(8)°. The crystal structure is stabilized by intermolecular π...π and C–H...π interactions.     

Structure of 1-(2,6-dimethylphenyl)-<Emphasis Type="Italic">N</Emphasis>-hydroxy-4,4-dimethyl-2,5-dioxo-<Emphasis Type="Italic">N</Emphasis>-phenyl-3-pyrrolidine carboxamide

The title compound is crystallized in the monoclinic space group P2₁/c with cell parameters a = 7.499, b = 13.336, c = 19.390 Å, β = 99.716°, V = 1911.4 ų, Z = 4, D _cal = 1.273 Mg/m³ at T = 120 K. The structure is refined by full-matrix least-squares procedures to final R ₁ = 0.0548 and wR ₂ = 0.1089 for 3424 reflections. Two phenyl rings are noncoplanar with regard to each other and pyrrolidine core. The structure contains intramolecular hydrogen bond.     

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,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.     

Synthesis and Characterization of <Emphasis Type="Italic">N,N</Emphasis>-di(prop-2-ynyl)-<Emphasis Type="Italic">p</Emphasis>-toluidine

Abstract  

In order to investigate the intramolecular [4 + 2] cycloaddition, we prepared some new tertiary N-(5-substituted-2-furfuryl)-N-prop-2-ynyl-p-toluidines [Hergold-Brundić et al., Acta Cryst C56:e520, 2000; Mance and Jakopčić, Mol Divers 9:229, 2005; Mance, “unpublished results”] by the alkylation of secondary N-(5-substituted-2-furfuryl)-p-toluidines with the propargyl-bromide [Mance and Šindler-Kulyk, Synth Commun 26:923, 1996]. In the course of preparation of N-(5-methoxy-2-furfuryl)-N-prop-2-ynyl-p-toluidine [Mance, “unpublished results”], besides the main product (compound 1) (Scheme 1) we obtained N,N-di(prop-2-ynyl)-p-toluidine (compound 2) as the colourless crystals. The title compound 2, N,N-di(prop-2-ynyl)-p-toluidine, C₁₃H₁₃N, crystallizes in monoclinic C 2/c space group with unit cell parameters: a = 19.5319(9) ?, b = 7.5230(3) ?, c = 15.9000(7) ?, β = 112.554(5)°, V = 2157.64(18) ?³, Z = 8. The crystal structure is dominated by van der Waals forces only. The bond distances around amine N atom correspond to σ dominated bonds (1.467(2), 1.462(2) and 1.419(2) ?). The angles sum around amine N atom is in accord with sp³ hybridization (343°).     

Synthesis and Crystal Structure of Bis[<Emphasis Type="Italic">N</Emphasis>-{(<Emphasis Type="Italic">S</Emphasis>)-1-Phenylethyl}-<Emphasis Type="Italic">N</Emphasis>-{1-(2-Pyridinyl)Methyl}Amine] Zinc(II) Perchlorate

Abstract  

The reaction of N-[(S)-1-phenylethyl]-N-[1-(2-pyridinyl)methyl]amine (PEPMA) with Zn(ClO₄)₂ affords (PEPMA)₂Zn(ClO₄)₂ at room temperature. The complex is characterized by elemental analysis, ¹H-MNR and X-ray crystallography. The crystal system is orthorhombic with space group of P2₁2₁2₁ and unit cell parameters: a = 8.6911(4), b = 9.7755(7), c = 37.275(2) ?, V = 3166.9(3) ?³, Z = 4, D _x  = 1.445 Mg/m³. The crystal structure reveals that zinc metal is ligated by two PEPMA ligands in a distorted tetrahedral fashion. Interestingly, both nitrogen atoms of amine at PEPMA to the central zinc metal exhibit (R)-configuration.     

Synthesis and Crystal Structures of Two Metal Complexes Formed in the Solvothermal Decomposition Reactions of <Emphasis Type="Italic">N</Emphasis>-Carboxyphenylenesulfonyl-S-Carboxymethyl-<Emphasis Type="SmallCaps">l</Emphasis>-Cysteine

Abstract  

The reactions of a new compound of N-Carboxyphenylenesulfonyl-S-Carboxymethyl-l-Cysteine (Cs-cmc) with Zn(II) or Co(II) salts in the presence of 4,4′-bipyridine (4,4′-bipy) led to the decomposition of Cs-cmc and produced [Zn(4,4′-bipy)(H₂O)₄]X₂ (X = p-sulfamoylbenzoate) 1 and [Co(4,4′-bipy)(H₂O)₄]Y·H₂O (Y = p-sulfonatobenzoate) 2, in which the decomposition products of Cs-cmc exist as free counter-anions. The single crystal X-ray diffraction analyses revealed that compound 1 crystallizes in monoclinic C2/c space group with a = 18.748(4) ?, b = 11.520(2) ?, c = 12.751(3) ?, β = 90.290(4)°, V = 2753.9(10) ?, Z = 4 and compound 2 crystallizes in orthorhombic Pca2₁ space group with a = 12.114(3) ?, b = 11.369(2) ?, c = 14.770(3) ?, V = 2034.1(7) ?, Z = 4. It was revealed that 1D chains were constructed from metal ions and 4,4′-bipy in both compounds. The 1D chains interact with the counter-anions by hydrogen bonds, forming 3D supramolecular structures.     

Specific stereochemical features of metallochelate complexes with tridentate <Emphasis Type="Italic">N,N,N</Emphasis>(<Emphasis Type="Italic">N,N</Emphasis>,O)-donating ligands

Earlier X-ray diffraction studies of a series of 12 adducts (I–XII) between metallochelate complexes [M = Co(II), Ni(II), and Cu(II)] with tridentate N,N,N(N,N,O)-donating Schiff bases (L) and monodentate or bidentate ligands (L′) revealed a similarity in the stereochemistry of these compounds. The coordination polyhedron of metal atoms in compounds I–XII is a tetragonal pyramid (bipyramid) with two vertices occupied competitively. The L ligand occupies three coordination sites in the base of the pyramid. The L′ ligand approaches the metal atom, as a rule, in a direction perpendicular to the basal plane. The fourth site in the base of the pyramid and the apical vertex are occupied competitively. Different patterns of occupation of these positions are observed: they include the donor atoms of both the L and L′ ligands.     

Synthesis of 2-arylidenebenzocycloalkanones containing <Emphasis Type="Italic">N</Emphasis>-donor heterocyclic rings

A series of 2-arylidenebenzocycloalkanones containing heterocyclic rings 1–8 were prepared and characterized by IR, ¹H NMR and elemental analyses. X-ray diffraction study of 6 reveals that the cyclohexyl ring of the 3,4-dihydronaphthalen-1(2H)-one adopts a chair conformation with a maximum deviation of 0.547(3) Å and makes dihedral angles of 52.24(17)° and 11.23(16)°, respectively, with the benzene plane and the mean plane of the benzimidazole ring.     

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.     

Synthesis and Crystal Structure of 7,8,9,10-Tetrahydro-2-bromo-cyclohepta[<Emphasis Type="Italic">b</Emphasis>]indol-6(5<Emphasis Type="Italic">H</Emphasis>)-one

The title compound, C₁₃H₁₂BrNO, was synthesized and characterised by IR, ¹H and ¹³C NMR spectroscopy. The proposed structure was confirmed by single crystal X-ray diffraction. The single crystal data revealed that the compound crystallizes in the triclinic system, sp. gr. P1, with Z = 2. The sevenmembered ring exhibits a slightly distorted envelope conformation. N–H···O hydrogen bonds form a centrosymmetric dimer, these interactions create a stair-like chain of molecules that interacts only loosely with neighbouring chains via van der Waals interactions, and C–H···π contacts are found in the crystal structure.     

Synthesis of <Emphasis Type="Italic">E</Emphasis> Isomer and Crystal Structures of <Emphasis Type="Italic">E</Emphasis> and <Emphasis Type="Italic">Z</Emphasis> Isomers of 3-(2,5-Dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile

Abstract Details of the synthesis of the E isomer of 3-(2,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile, and the X-ray crystal structures of both the E and Z isomers of this compound are presented. The E isomer crystallizes in the P2₁/c space group with cell parameters, a = 8.5659(17) ?, b = 16.399(3) ?, c = 11.224(2) ?, α = 90°, β = 95.27(3)°, γ = 90°and Z = 4. The Z isomer crystallizes in the Pca2₁ space group with cell parameters, a = 4.1223(8) ?, b = 19.113(4) ?, c = 19.453(4) ?, α = 90°, β = 90°, γ = 90° and Z = 4. Index Abstract Synthesis of E isomer and X-ray crystal structure determination of both E and Z isomers of 3-(2,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile are presented.      

Synthesis,Characterization and Crystal Structure of (<Emphasis Type="Italic">S</Emphasis>)-2-(2-Hydroxynaphthalen-6-yl)-<Emphasis Type="Italic">N</Emphasis>-((pyridin-4-yl)methyl) Propanamide

Abstract  

The synthesis, characterization and crystal structure of the title compound, (S)-2-(2-hydroxynaphthalen-6-yl)-N-((pyridin-4-yl)methyl) propanamide, is described. The salt is enantiomerically pure and crystallize in the orthorhombic P2₁2₁2₁ chiral space group with a = 7.9174(13) ?, b = 11.1583(18) ?, c = 11.2600(18) ?. Each molecule is linked to four neighboring molecules through the O–H···O and N–H···N hydrogen bonds into a supramolecular helical chain. The O–H···O and N–H···N hydrogen bonds lead to 24-membered open rings. Chains are further connected into layers via extensive interchain H···O and H···C short contacts.