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1.  4,4′-Di-tert-butyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol 
In the title compound, C25H36N2O2, the two tert-butyl-substituted benzene rings are inclined at an angle of 53.5 (3)° to one another. The imidazolidine ring has an envelope conformation with with one of the C atoms of the ethylene fragment as the flap. The structure displays two intra­molecular O—H⋯N hydrogen bonds that generate S(6) ring motifs. The crystal studied was a non-merohedral twin with a fractional contribution of 0.281(6) for the minor domain.
doi:10.1107/S1600536813017157
PMCID: PMC3770425  PMID: 24046710
2.  4,4′-Dimethyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol 
The imidazolidine ring in the title compound, C19H24N2O2, adopts a twist conformation and its mean plane (r.m.s. deviation = 0.19 Å) makes dihedral angles of 72.38 (9) and 71.64 (9)° with the two pendant aromatic rings. The dihedral angle between the phenyl rings is 55.94 (8)°. The mol­ecular structure shows the presence of two intra­molecular O—H⋯N hydrogen bonds between the phenolic hydroxyl groups and N atoms with graph-set motif S(6). In the crystal, C—H⋯O hydrogen bonds lead to the formation of chains along the b-axis direction.
doi:10.1107/S1600536812042808
PMCID: PMC3515265  PMID: 23284485
3.  4,4′-Difluoro-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol 
In the title compound, C17H18F2N2O2, the imidazolidine ring system exists in a twist conformation. The mean plane through this ring system forms dihedral angles of 80.8 (8)° and 66.2 (13)°, with the benzene rings. The dihedral angle between the benzene rings is 52.0 (14)°. Two intra­molecular O—H⋯N hydrogen bonds each generate S(6) ring motifs. In the crystal, weak C—H⋯O hydrogen bonds form dimers, which are connected by further C—H⋯O inter­actions.
doi:10.1107/S1600536812040329
PMCID: PMC3470394  PMID: 23125807
4.  2,2′-[Imidazolidine-1,3-diylbis(methyl­ene)]diphenol 
In the title mol­ecule, C17H20N2O2, the imidazolidine ring adopts a twist conformation. The mean plane through the five atoms of the imidazolidine ring makes dihedral angles of 70.18 (4) and 74.14 (4)° with the planes of the two aromatic rings. The dihedral angle between the benzene rings is 53.11 (5)°. Both phenol –OH groups form intra­molecular hydrogen bonds to the N atoms, with graph-set motif S(6). In the crystal, pairs of O—H⋯O hydrogen bonds link the mol­ecules into dimers with R 4 4(18) ring motifs. The crystal packing is further stabilized by C—H⋯O and weak C—H⋯π inter­actions.
doi:10.1107/S1600536811053748
PMCID: PMC3254510  PMID: 22259455

Results 1-4 (4)