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1.  (E)-N-{[6-Chloro-4-(4-chloro­phen­yl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl­ene}benzene-1,2-diamine: a three-dimensional framework structure built from only two hydrogen bonds 
The mol­ecules of the title compound, C26H19Cl2N5, are conformationally chiral, with none of the aryl groups coplanar with the pyrazolo[3,4-b]pyridine core of the mol­ecule. A single unique N—H⋯N hydrogen bond links the mol­ecules into two symmetry-related sets of C(11) chains running parallel to the [011] and [01] directions, respectively, and these two sets of chains are linked into a continuous three-dimensional framework structure by a single unique C—H⋯N hydrogen bond which forms a chain parallel to the [100] direction.
doi:10.1107/S0108270110004026
PMCID: PMC2855570  PMID: 20203411
2.  Hydrogen-bonding patterns in two aroylthio­carbamates and two aroylimidothio­carbonates 
In O-ethyl N-benzoyl­thio­carbamate, C10H11NO2S, the mol­ecules are linked into sheets by a combination of two-centre N—H⋯O and C—H⋯S hydrogen bonds and a three-centre C—H⋯(O,S) hydrogen bond. A combination of two-centre N—H⋯O and C—H⋯O hydrogen bonds links the mol­ecules of O-ethyl N-(4-methyl­benzoyl)thio­carbamate, C11H13NO2S, into chains of rings, which are linked into sheets by an aromatic π–π stacking inter­action. In O,S-diethyl N-(4-methyl­benzoyl)imidothio­carbonate, C13H17NO2S, pairs of mol­ecules are linked into centrosymmetric dimers by pairs of symmetry-related C—H⋯π(arene) hydrogen bonds, while the mol­ecules of O,S-diethyl N-(4-chloro­benzoyl)imidothio­carbonate, C12H14ClNO2S, are linked by a single C—H⋯O hydrogen bond into simple chains, pairs of which are linked by an aromatic π–π stacking inter­action to form a ladder-type structure.
doi:10.1107/S0108270110005032
PMCID: PMC2855573  PMID: 20203412
3.  7-Amino-5-methyl-2-phenyl-6-(phenyl­diazenyl)pyrazolo[1,5-a]pyrimidine crystallizes with Z′ = 2: pseudosymmetry and the formation of complex sheets built from N—H⋯N and C—H⋯π(arene) hydrogen bonds 
The title compound, C19H16N6, crystallizes with Z′ = 2 in the space group P21/n. The two mol­ecules in the selected asym­metric unit are approximate mirror images of one another; most corresponding pairs of atoms are related by an approximate half-cell translation along [100]. Each mol­ecule contains an intra­molecular N—H⋯N hydrogen bond and the mol­ecules are linked into complex sheets by a combination of two inter­molecular N—H⋯N and four C—H⋯π(arene) hydrogen bonds. Comparisons are made with some other 7-amino­pyrazolo[1,5-a]pyrimidines.
doi:10.1107/S0108270110003549
PMCID: PMC2855586  PMID: 20203410
4.  3-[(E)-(3-tert-Butyl-1-phenyl-1H-pyrazol-5-yl)imino­methyl]quinolin-2(1H)-one: chains built by π-stacking of hydrogen-bonded R 2 2(8) dimers 
In the title compound, C23H22N4O, there is evidence for some bond fixation in the aryl component of the quinolinone unit. Pairs of mol­ecules related by inversion are linked into R 2 2(8) dimers by almost linear N—H⋯O hydrogen bonds, and dimers related by inversion are linked into chains by a single aromatic π–π stacking inter­action.
doi:10.1107/S0108270109033861
PMCID: PMC2758068  PMID: 19805879
5.  5-Nitro-N 4,N 6-diphenyl­pyrimidine-4,6-diamine: polarized mol­ecules linked into π-stacked chains via three-centre C—H⋯(O)2 hydrogen bonds 
Mol­ecules of the title compound, C16H13N5O2, have no inter­nal symmetry despite the symmetric pattern of substitution in the pyrimidine ring. The intra­molecular distances indicate polarization of the electronic structure. There are two intra­molecular N—H⋯O hydrogen bonds and mol­ecules are linked into centrosymmetric dimers by pairs of three-centre C—H⋯(O)2 hydrogen bonds. These dimers are linked into chains by means of a π–π stacking inter­action.
doi:10.1107/S0108270109029618
PMCID: PMC2737422  PMID: 19726856
6.  2-Amino-3-methyl-6-[meth­yl­(phen­yl)­amino]-5-nitro­pyrimidin-4(3H)-one: polarized mol­ecules within hydrogen-bonded sheets 
The pyrimidinone ring in the title compound, C12H13N5O3, is effectively planar, despite the presence of five substituents. The bond distances provide evidence for significant polarization of the electronic structure, with charge separation, and the mol­ecules are linked into sheets by a combination of N—H⋯O and N—H⋯π(arene) hydrogen bonds. Comparisons are made with the mol­ecular and supra­molecular structures of the precursor compound 2-amino-6-[meth­yl(phen­yl)amino]-5-nitro­pyrimidin-4(3H)-one.
doi:10.1107/S010827010902887X
PMCID: PMC2737423  PMID: 19726857
7.  (E)-3-(4-Methyl­phen­yl)-2-(2-thien­yl)­acrylonitrile has Z′ = 0.75 in the space group C2/m: fourfold disordered mol­ecules lie in channels enclosed by fully ordered mol­ecules 
The title compound, C14H11NS, crystallizes with Z′ = 0.75 in the space group C2/m. Two independent mol­ecules are present, one of which lies with all the non-H atoms on a mirror plane, while the other is fourfold disordered across a site of 2/m symmetry. The ordered mol­ecules are stacked such that they enclose continuous channels running along twofold rotation axes, and the disordered mol­ecules are positioned within these channels.
doi:10.1107/S0108270109029667
PMCID: PMC2737424  PMID: 19726858
8.  Four differently substituted 2-aryl-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepines: hydrogen-bonded structures in one, two and three dimensions 
In (2RS,4SR)-7-chloro-2-exo-(2-chloro-6-fluoro­phen­yl)-2,3,4,5-tetra­hydro-1H-1,4-epoxy-1-benzazepine, C16H12Cl2FNO, (I), mol­ecules are linked into chains by a single C—H⋯π(arene) hydrogen bond. (2RS,4SR)-2-exo-(2-Chloro-6-fluoro­phen­yl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine, C16H13ClFNO, (II), is isomorphous with compound (I) but not strictly isostructural with it, as the hydrogen-bonded chains in (II) are linked into sheets by an aromatic π–π stacking inter­action. The mol­ecules of (2RS,4SR)-7-methyl-2-exo-(4-methyl­phenyl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine, C18H19NO, (III), are linked into sheets by a combination of C—H⋯N and C—H⋯π(arene) hydrogen bonds. (2S,4R)-2-exo-(2-Chloro­phen­yl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine, C16H14ClNO, (IV), crystallizes as a single enantiomer and the mol­ecules are linked into a three-dimensional framework structure by a combination of one C—H⋯O hydrogen bond and three C—H⋯π(arene) hydrogen bonds.
doi:10.1107/S0108270109030339
PMCID: PMC2737425  PMID: 19726863
9.  Sterically shielded pyramidal amino groups in two 4,4′-(aryl­methyl­ene)bis­(6-allyl-3-chloro-2-methyl­aniline) derivatives 
4,4′-(Phenyl­methyl­ene)bis­(6-allyl-3-chloro-2-methyl­aniline), C27H28Cl2N2, (I), and 4,4′-(2-thienylmethyl­ene)bis­(6-allyl-3-chloro-2-methyl­aniline), C25H26Cl2N2S, (II), adopt similar mol­ecular conformations, although the thienyl group in (II) exhibits orientational disorder over two sets of sites with occupancies of 0.614 (3) and 0.386 (3). The amino groups in both compounds are pyramidal. A single N—H⋯N hydrogen bond links the mol­ecules of (I) into cyclic centrosymmetric dimers. Mol­ecules of (II) are linked by an ordered C—H⋯π(arene) hydrogen bond to form cyclic centrosymmetric dimers, and these dimers are linked into statistically inter­rupted chains by a second C—H⋯π(arene) hydrogen bond involving a donor in the minor component of the disordered thienyl unit.
doi:10.1107/S0108270109031175
PMCID: PMC2737426  PMID: 19726866
10.  2-{2-[2-(4-Methoxy­benzoyl)ethyl­amino]-4-nitro­anilino}ethyl acetate: complex sheets built from five independent hydrogen bonds 
The mol­ecules of the title compound, C20H23N3O6, are almost completely planar, apart from the H atoms bonded to tetra­hedral C atoms. A combination of five hydrogen bonds, one of the N—H⋯O type and two each of the C—H⋯O and C—H⋯π(arene) types, links the mol­ecules into complex sheets.
doi:10.1107/S0108270109032235
PMCID: PMC2737427  PMID: 19726867
11.  Different hydrogen-bonded structures in three 2-thienyl-substituted tetra­hydro-1,4-ep­oxy-1-benzazepines 
The mol­ecules of (2RS,4SR)-2-exo-(5-bromo-2-thienyl)-7-chloro-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine, C14H11BrClNOS, (I), are linked into cyclic centrosymmetric dimers by C—H⋯π(thienyl) hydrogen bonds. Each such dimer makes rather short Br⋯Br contacts with two other dimers. In (2RS,4SR)-2-exo-(5-methyl-2-thienyl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine, C15H15NOS, (II), a com­bination of C—H⋯O and C—H⋯π(thienyl) hydrogen bonds links the mol­ecules into chains of rings. A more complex chain of rings is formed in (2RS,4SR)-7-chloro-2-exo-(5-methyl-2-thienyl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine, C15H14ClNOS, (III), built from a combination of two independent C—H⋯O hydrogen bonds, one C—H⋯π(arene) hydrogen bond and one C—H⋯π(thienyl) hydro­gen bond.
doi:10.1107/S0108270109031199
PMCID: PMC2737428  PMID: 19726868
12.  Eight 7-benzyl-3-tert-butyl-1-phenyl­pyrazolo[3,4-d]oxazines, encompassing structures containing no inter­molecular hydrogen bonds, and hydrogen-bonded structures in one, two or three dimensions 
7-Benzyl-3-tert-butyl-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C22H25N3O, (I), and 3-tert-butyl-7-(4-methyl­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C23H27N3O, (II), are isomorphous in the space group P21, and mol­ecules are linked into chains by C—H⋯O hydrogen bonds. In each of 3-tert-butyl-7-(4-methoxy­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C23H27N3O2, (III), which has cell dimensions rather similar to those of (I) and (II), also in P21, and 3-tert-butyl-1-phenyl-7-[4-(trifluoro­meth­yl)benz­yl]-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C23H24F3N3O, (IV), there are no direction-specific inter­actions between the mol­ecules. In 3-tert-butyl-7-(4-nitro­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C22H24N4O3, (V), a combination of C—H⋯O and C—H⋯N hydrogen bonds links the mol­ecules into complex sheets. There are no direction-specific inter­actions between the mol­ecules of 3-tert-butyl-7-(2,3-dimethoxy­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C24H29N3O3, (VI), but a three-dimensional framework is formed in 3-tert-butyl-7-(3,4-methyl­enedioxy­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C23H25N3O3, (VII), by a combination of C—H⋯O, C—H⋯N and C—H⋯π(arene) hydrogen bonds, while a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds links the mol­ecules of 3-tert-butyl-1-phenyl-7-(3,4,5-trimethoxy­benz­yl)-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C25H31N3O4, (VIII), into complex sheets. In each compound, the oxazine ring adopts a half-chair conformation, while the orientations of the pendent phenyl and tert-butyl substituents relative to the pyrazolo[3,4-d]oxazine unit are all very similar.
doi:10.1107/S0108270109028017
PMCID: PMC2720151  PMID: 19652329

Results 1-12 (12)