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1.  1-Heptyl-1,3,6,8-tetraaza­tricyclo­[4.3.1.13,8]undecan-1-ium iodide 
The title compound C14H29N4 +·I− salt, was obtained by the reaction of cage adamanzane-type aminal 1,3,6,8-tetra­aza­tricyclo­[4.3.1.13,8]undecane with heptyl iodide. In the cation, the bond lengths and angles are within normal ranges, except for one N—C(ring) bond distance of 1.542 (3) Å, which is unexpectedly long compared with related compounds. In the crystal, ions are linked through C—H⋯I hydrogen bonds. The crystal studied was a non-merohedral twin with a minor twin domain of 6.56 (5)%.
doi:10.1107/S1600536811036403
PMCID: PMC3201392  PMID: 22064969
2.  Synthesis and structural studies of a new class of quaternary ammonium salts, which are derivatives of cage adamanzane type aminal 1, 3, 6, 8-tetraazatricyclo[4.3.1.13,8]undecane (TATU) 
Background
Novel mono N-alkyl quaternary ammonium salts (3a-f) were prepared using the Menschutkin reaction from the cage adamanzane type aminal 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane (TATU) and alkyl iodides, such as methyl, ethyl, propyl, butyl, pentyl and hexyl iodide (2a-f), in dry acetonitrile at room temperature.
Results
The structures of these new quaternary ammonium salts were established using various spectral and electrospray ionization mass spectrometry (ESI-MS) analyses. Compound (3b) was also analyzed using X-ray crystallography.
Conclusion
It was noted that alkyl chain length did not significantly affect the reaction because all employed alkyl iodide electrophiles reacted in a similar fashion with the aminal 1 to produce the corresponding mono N-quaternary ammonium salts, which were characterized by spectroscopic and analytical techniques.
doi:10.1186/1752-153X-5-55
PMCID: PMC3189110  PMID: 21933409
3.  Diaqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4 N 1,N 4,N 8,N 11)copper(II) dihepta­noate dihydrate 
The CuII atom in the title salt, [Cu(C10H24N4)(H2O)2][CH3(CH2)5CO2]2·2H2O, is chelated by the four N atoms of the 1,4,8,11-tetra­aza­cyclo­tetra­decane (cyclam) ligand and is coordinated by two water mol­ecules in a tetra­gonally Jahn–Teller-distorted octa­hedral geometry. The CuII atom lies on a center of inversion. The cations, anions and uncoordinated water mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, forming a layer structure parallel to (100). The alkyl chain of the anion is disordered over two positions in a 0.82 (1):0.18 (1) ratio.
doi:10.1107/S1600536810025687
PMCID: PMC3007509  PMID: 21588132
4.  Diaqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4 N 1,N 4,N 8,N 11)copper(II) bis­(4-methyl­benzoate) monohydrate 
The CuII atom in the title salt, [Cu(C10H24N4)(H2O)2](C8H7O2)2·H2O, is chelated by the four N atoms of the 1,4,8,11-tetra­aza­cyclo­tetra­decane (cyclam) ligand and is coordinated by two water mol­ecules in a Jahn–Teller-type of tetra­gonally distorted octa­hedral geometry. The cations, anions and lattice water mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds to form a layer structure parallel to (001).
doi:10.1107/S1600536810026012
PMCID: PMC3007233  PMID: 21588135
5.  Diaqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4 N 1,N 4,N 8,N 11)copper(II) bis­(2,3,4,5,6-penta­fluoro­benzoate) dihydrate 
The CuII atom in the title salt, [Cu(C10H24N4)(H2O)2](C6F5CO2)2·2H2O, is chelated by the four N atoms of the 1,4,8,11-tetra­aza­cyclo­tetra­decane (cyclam) ligand and is coordinated by two water mol­ecules in a Jahn–Teller-type tetra­gonally distorted octa­hedral geometry. The CuII atom lies on a center of inversion. The cations, anions and uncoordinated water mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, forming a layer structure parallel to (001).
doi:10.1107/S1600536810025705
PMCID: PMC3007516  PMID: 21588134
6.  Diaqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4 N 1,N 4,N 8,N 11)copper(II) dideca­noate dihydrate 
The CuII atom in the title salt, [Cu(C10H24N4)(H2O)2][CH3(CH2)8CO2]2·2H2O, is chelated by the four N atoms of the 1,4,8,11-tetra­aza­cyclo­tetra­decane (cyclam) ligand and is coordinated by two water mol­ecules in a Jahn–Teller-type tetra­gonally distorted octa­hedral geometry. The CuII atom lies on a center of inversion. The cations, anions and uncoordinated water mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, forming a layer structure parallel to (001).
doi:10.1107/S1600536810025699
PMCID: PMC3007572  PMID: 21588133
7.  Diaqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4 N 1,N 4,N 8,N 11)copper(II) didodeca­noate dihydrate 
The title compound, [Cu(C10H24N4)(H2O)2][CH3(CH2)10CO2]2·2H2O, consists of one cationic copper(II) complex, two dodeca­noate anions and two water solvent mol­ecules. The CuII atom is located on an inversion center and is chelated by the four aza N atoms of the neutral 1,4,8,11-tetra­aza­cyclo­tetra­decane (cyclam) ligand and by two water mol­ecules in axial positions, giving an octa­hedral coordination geometry, distorted as a consequence of the Jahn–Teller effect. The uncoordinated water mol­ecules link the complex cations and the dodeca­noate counter-ions through O—H⋯O hydrogen bonding, forming a layer structure parallel to (001). Inter­molecular N—H⋯O inter­actions also occur.
doi:10.1107/S1600536811012773
PMCID: PMC3089101  PMID: 21754311
8.  1,4,10,13-Tetra­oxa-7,16-diazo­nia­cyclo­octa­decane bis­(1H-pyrrole-2-carboxyl­ate) 
In the title salt, C12H28N2O4 2+·2C5H4NO2 −, the 1,4,10,13-tetra­oxa-7,16-di­aza­cyclo­octa­decane dication possesses inversion symmetry. In the crystal, the pyrrole-carboxyl­ate anions are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers. These dimers are linked by the dications, via N—H⋯O hydrogen bonds, forming chains propagating along [110].
doi:10.1107/S1600536813016176
PMCID: PMC3770382  PMID: 24046667
9.  2,3,5-Triphenyl-2H-tetra­zol-3-ium iodide 
The asymmetric unit of the title mol­ecular salt, C19H15N4 +·I−, contains four 2,3,5-triphenyl-2H-tetra­zol-3-ium cations and five iodide anions, with two of the latter lying on crystallographic inversion centres. In each cation, the tetra­zole ring is essentially planar (r.m.s. deviations = 0.004–0.007 Å). The dihedral angles between the tetra­zole ring and its three attached benzene rings in the four independent cations are: 12.9 (4), 67.0 (4), 48.1 (4); 20.8 (4), 51.1 (4), 62.3 (4); 11.4 (4), 52.3 (4), 47.3 (4) and 6.0 (4), 85.7 (4), 43.5 (4)°. A C—H⋯I hydrogen bond and C—H⋯π inter­actions are observed in the crystal.
doi:10.1107/S1600536812033661
PMCID: PMC3435649  PMID: 22969522
10.  Ethyl 23-benzyl-8,11,14-trioxa-23,28,29-triaza­penta­cyclo­[19.7.1.02,7.015,20.022,27]nona­cosa-2,4,6,15(20),16,18,21,26-octa­ene-26-carboxyl­ate 
The title compound, C33H35N3O5, is the product of the multicomponent condensation of 1-benzyl-4-eth­oxy­carbonyl­piperidin-3-one with 1,5-bis­(2-formyl­phen­oxy)-3-oxapentane and ammonium acetate. The mol­ecule comprises a penta­cyclic system containing the aza-14-crown-4-ether macrocycle, tetra­hydro­pyrimidine, tetra­hydro­pyridine and two benzene rings. The aza-14-crown-4-ether ring adopts a bowl conformation with a dihedral angle of 62.37 (5)° between the benzene rings. The tetra­hydro­pyrimidine ring has an envelope conformation with the chiral C atom as the flap, whereas the tetra­hydro­pyridine ring adopts a distorted chair conformation. Two amino groups are involved in intra­molecular N—H⋯O hydrogen bonds. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into layers parallel to the ab plane.
doi:10.1107/S1600536813007241
PMCID: PMC3629615  PMID: 23634102
11.  catena-Poly[[[(5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4 N)nickel(II)]-μ-oxido-[dioxidotungstate(VI)]-μ-oxido] tetra­hydrate] 
In the title compound, {[NiWO4(C16H36N4)]·4H2O}n, the NiII ion lies on an inversion center and is octahedrally coordinated by four N atoms of the tetradentate macrocyclic 5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane (L) ligand in the equatorial plane and two O atoms of [WO4]2− anions in axial positions. Each [WO4]2− anion bridges two adjacent [NiL]2+ cations, forming a chain along [001]. The chains are further connected via N—H⋯O, O—H⋯O and C—H⋯O hydrogen-bonding inter­actions, generating a three-dimensional structure.
doi:10.1107/S1600536812034538
PMCID: PMC3435596  PMID: 22969469
12.  Bis(nitrato-κO)(5,7,12,14-tetra­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane-6,13-diaminium-κ4 N 1,N 4,N 8,N 11)copper(II) dinitrate tetra­hydrate 
In the title compound, [Cu(NO3)2(C14H36N6)](NO3)2·4H2O, the CuII atom, lying on an inversion center, is six-coordinated in a distorted octa­hedral environment by four N atoms from a centrosymmetric 14-membered tetra­aza­cyclo­tetra­decane macrocyclic ligand and two O atoms from two nitrate anions. The supra­molecular network is consolidated by extensive O—H⋯O and N—H⋯O hydrogen-bonding inter­actions.
doi:10.1107/S1600536810023342
PMCID: PMC3006849  PMID: 21587749
13.  Neoaustin: a meroterpene produced by Penicillium sp. 
The title meroterpene neoaustin {systematic name: (1′S,2′R,3S,7′R,9′S,11′S,12′R)-11′-hydr­oxy-2,2,2′,9′,12′-penta­methyl-6′,15′-dimethyl­ene-2,6-dihydro-13′-oxaspiro­[pyran-3,5′-tetra­cyclo­[7.5.1.01,11.02,7]penta­deca­ne]-6,10′,14′-trione}, C25H30O6, comprises five rings, three six-membered and two five-membered. The absolute configuration was established based on [αD] = +166.91° (c 1.21, CH2Cl2). In the crystal, the mol­ecules are connected into a supra­molecular helical chain via O—H⋯O hydrogen bonds reinforced by C—H⋯O contacts.
doi:10.1107/S1600536809006618
PMCID: PMC2968484  PMID: 21582264
14.  1-(Ferrocen-1-ylmeth­yl)-3-methyl­imidazol-3-ium iodide 
The structure of the title compound, [Fe(C5H5)(C10H12N2)]I, consists of a 1-(ferrocen-1-ylmeth­yl)-3-methyl­imidazolium cation which is counter-balanced by an iodide anion. The cyclo­penta­dienyl (Cp) rings of the ferrocene unit have a slightly staggered conformation skewed from an ideal eclipsed conformation by an angle of 3.5 (6)°. The inter­planar angle between the Cp and the imidazole ring is 67.94 (2)°.
doi:10.1107/S1600536812045400
PMCID: PMC3588731  PMID: 23468696
15.  (1,2-Dicarba-closo-dodeca­boran­yl)trimethyl­methanaminium iodide 
The title compound, [1-(CH3)3NCH2-1,2-C2B10H11]+·I− or C6H22B10N+·I−, was obtained by the reaction of (1,2-dicarba-closo-dodeca­boran­yl)dimethyl­methanamine with methyl iodide. The asymmetric unit contains two iodide anions and two (o-carboran­yl)tetra­methyl­ammonium cations. The bond lengths and angles in the carborane cage are within normal ranges, but the N—Cmethyl­ene—Ccage angle is very large [120.2 (2)°] because of repulsion between the carborane and tetra­methyl­ammonium units. In the crystal, ions are linked through C—H⋯I hydrogen bonds.
doi:10.1107/S160053681102928X
PMCID: PMC3213586  PMID: 22091163
16.  1-Butyl-3-ethyl-1H-benzimidazol-3-ium tetra­fluoro­borate 
In the title salt, C13H19N2 +·BF4 −, an ionic liquid, the butyl and ethyl substituents bonded to the N atoms of the imidazole ring [r.m.s. deviation = 0.019 (1) Å] adopt equatorial positions. The crystal structure exhibits slipped π–π inter­actions between the imidazole and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.529 (2) Å]. In the tetra­fluoro­borate anion, the B and F atoms are disordered over two sets of sites with site-occupancy factors of 0.813 (7) and 0.187 (7).
doi:10.1107/S1600536812037476
PMCID: PMC3470219  PMID: 23125663
17.  (C-meso-N-meso-5,12-Dimethyl-7,14-diphenyl-1,4,8,11-tetra­aza­cyclo­tetra­deca-4,11-diene)nickel(II) bis­[O,O′-bis­(4-methyl­phen­yl) dithio­phosphate] 
The title complex, [Ni(C24H32N4)](C14H14O2PS2)2, comprises a centrosymmetric [Ni(meso-diphen­yl[14]dien)]2+ dication (meso-diphen­yl[14]dien is C-meso-N-meso-5,12-dimethyl-7,14-diphenyl-1,4,8,11-tetra­aza­cyclo­tetra­deca-4,11-diene) and two O,O′-bis­(4-methyl­phen­yl) dithio­phosphate anions. The NiII ion lies on an inversion center and is chelated by a tetra­amine macrocycle ligand in a slightly distorted NiN4 square-planar geometry. Two S atoms from symmetry-related anions are located in pseudo-axial positions with respect to the NiII ion, with Ni⋯S distances of 3.1869 (8) Å. In the crystal, bifurcated inter­molecular N—H⋯S(S) hydrogen bonds connect cations and pairs of anions into three-component clusters. Weak inter­molecular C—H⋯S hydrogen bonds link these clusters into chains along [100].
doi:10.1107/S160053681004849X
PMCID: PMC3011755  PMID: 21589325
18.  meso-4,4′-Difluoro-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}diphenol 
In the crystal structure of the title compound, C21H24F2N2O2, there are two intra­molecular O—H⋯N hydrogen bonds involving the N atoms of the imidazolidine ring and the hy­droxy groups. The crystal studied was a meso compound obtained by the reaction of the aminal (2S,7R,11S,16R)-1,8,10,17-tetra­aza­penta­cyclo­[8.8.1.18,17.02,7.011,16]cosane with 4-fluoro­phenol. The imidazolidine ring has a twisted conformation with a CH—CH—N—CH2 torsion angle of 44.99 (14)° and, surprisingly, the lone pairs of the N atoms are disposed in a syn isomerism, making the title compound an exception to the typical ‘rabbit-ear effect’ in 1,2-diamines. In the crystal, molecules are linked via C—H⋯F hydrogen bonds, forming chains along the c-axis direction. These chains are linked via another C—H⋯F hydrogen bond, forming a three-dimensional network.
doi:10.1107/S1600536813000305
PMCID: PMC3569752  PMID: 23424498
19.  (20S)-Dammar-24-ene-3β,20-diol monohydrate from the bark of Aglaia exima (Meliaceae) 
In the title compound {systematic name: (1R,2R,5R,7R,10R,11R,14S,15R)-14-[(2S)-2-hy­droxy-6-methyl­hept-5-en-2-yl]-2,6,6,10,11-penta­methyl­tetra­cyclo­[8.7.0.02,7.011,15]hepta­decan-5-ol monohydrate}, C30H52O2·H2O, the three fused cyclo­hexane rings adopt chair conformations and the hy­droxy substituent of one of these occupies an axial position. The fused cyclo­pentane ring adopts an envelope conformation (with the flap atom being the C atom bearing the methyl group) and the 3-methyl­but-2-enyl portion of its substituent is disordered over three sets of sites in a 0.413 (7):0.250 (7):0.337 (7) ratio. The O atoms of both water mol­ecules occupy special positions of 2 site symmetry. In the crystal, Os—H⋯Ow and Ow—H⋯Os (s = steroid and w = water) hydrogen bonds link hy­droxy groups and water mol­ecules, forming a three-dimensional network. The crystal studied was found to be a non-merohedral twin with a 0.518 (1):0.482 (1) component ratio.
doi:10.1107/S1600536812034976
PMCID: PMC3435729  PMID: 22969600
20.  (Cinnamato-κ2 O,O′)(5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4 N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate 
In the title compound, [Ni(C9H7O2)(C16H36N4)]ClO4·H2O, the macrocyclic 5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane ligand (L) folds around the NiII atom, which is also chelated by the carboxyl­ate group. The geometry is a distorted N4O2 octa­hedron. In the crystal, adjacent mol­ecules are connected by O—H⋯O and N—H⋯O hydrogen bonds into a zigzag chain parallel to [010].
doi:10.1107/S1600536812032175
PMCID: PMC3414150  PMID: 22904757
21.  Diaqua­[(1R,2S,4R,8R,9S,11R)-2,9-di­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane]nickel(II) dichloride dihydrate 
The crystal structure of the title complex, [Ni(C12H28N4)(H2O)2]Cl2·2H2O, displays O—H⋯Cl and O—H⋯O hydrogen bonding. The tetra­aza­cyclo­tetra­decane ligand inter­acts with the NiII atom in the cis V configuration and the final two ligand binding sites are occupied by water.
doi:10.1107/S160053681203276X
PMCID: PMC3414157  PMID: 22904764
22.  Tricarbonyl(chlorodiphenylstannyl){η5-[2-(dimethylamino)ethyl]cyclopenta­dienyl}molybdenum 
Reaction of the tricarbon­yl{η5-[2-(dimethyl­amino)eth­yl]cyclo­penta­dien­yl}molybdenum anion and dichlorido­diphenyl­stannane affords the title compound, [MoSn(C6H5)2Cl(C9H14N)(CO)3], which exhibits a four-legged piano-stool geometry with chlorido­diphenyl­stannyl ligands unperturbed by the pendant 2-(dimethyl­amino)ethyl groups. The Mo—Sn bond length [2.7584 (5) Å] and the distortion of the tetra­hedral tin coordination geometry are similar to those observed in related tin-substituted tricarbonyl­molybdenum and -tungsten complexes.
doi:10.1107/S1600536809014329
PMCID: PMC2977605  PMID: 21583791
23.  [(1-Azulen­yl)methane­thiol­ato-κS](1,4,8,12-tetra­azacyclo­penta­decane-κ4 N)zinc(II) perchlorate 
In the title compound, [Zn(C11H26N4)(C11H9S)]ClO4, the ZnII atom is five-coordinated by four N atoms from a neutral 1,4,8,12-tetra­azacyclo­penta­decane aza-macrocycle mol­ecule, and one S atom from an azulenylmethane­thiol­ate ligand. Only monomers are found in the crystal. The coordination geometry can be described as trigonal bipyramidal, with the thiol­ate group in an equatorial position. The Zn—N and Zn—S distances are in the usual ranges for this type of complex.
doi:10.1107/S1600536807047514
PMCID: PMC2915133  PMID: 21200551
24.  2,3,5-Triphenyl-2H-tetra­zol-3-ium tetra­phenyl­borate 
In the title salt, C19H15N4 +·C24H20B−, the tetra­phenyl­borate anion is in a tetra­hedral geometry around the B atom [C—B—C angles of 107.10 (9)–111.79 (9)°]. In the cation, the tetra­zole ring makes dihedral angles of 3.04 (7), 51.75 (7) and 51.13 (7)° with the attached phenyl rings. In the crystal, C—H⋯π inter­actions link the cations and anions into ion pairs.
doi:10.1107/S1600536812032941
PMCID: PMC3415008  PMID: 22904995
25.  (5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetra­aza­cyclo­tetra­deca-4,11-diene)nickel(II) bis­[O,O′-bis­(4-tert-butyl­phen­yl) dithio­phosphate] 
The title salt, [Ni(C16H32N4)](C20H26O2PS2)2, comprises a centrosymmetric [Ni(Me6[14]dieneN4)]2+ dication (Me6[14]dieneN4 is 5,7,7,12,14,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­deca-4,11-diene) and two O,O′-bis­(4-tert-butyl­phen­yl) dithio­phosphate anions. The NiII ion lies on an inversion centre and displays a slightly distorted NiN4 square-planar chelation arrangement with four N atoms from the Me6[14]dieneN4 macrocycle. Two S atoms from symmetry-related anions are located in pseudo-axial positions with respect to the NiII ion, with Ni⋯S distances of 3.2991 (7) Å. Inter­molecular N—H⋯S and C—H⋯S hydrogen bonds link the complex cation and pair of anions into a 1:2 type salt.
doi:10.1107/S1600536810049615
PMCID: PMC3050131  PMID: 21522543

Results 1-25 (156610)