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4,4'-Dichloro-2,2'-[(3aR,7aR/3aS,7aS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl)bis-(methyl-ene)]diphenol.

ABSTRACT: Mol-ecules of the the title compound, C(21)H(24)Cl(2)N(2)O(2), are located on a twofold rotation axis, which passes through the C atom linking the two N atoms. Two intra-molecular O-H?N hydrogen bonds were observed. In the crystal, non-classical inter-molecular C-H?O hydrogen bonds link the mol-ecules into chains along the a axis. The crystal studied was a racemic twin.

SUBMITTER: Rivera A

PROVIDER: S-EPMC2983180 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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4,4'-Dichloro-2,2'-[(3aR,7aR/3aS,7aS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl)bis-(methyl-ene)]diphenol.

Rivera Augusto A Quiroga Diego D Ríos-Motta Jaime J Dušek Michal M Fejfarová Karla K

Acta crystallographica. Section E, Structure reports online 20100930 Pt 10

Mol-ecules of the the title compound, C(21)H(24)Cl(2)N(2)O(2), are located on a twofold rotation axis, which passes through the C atom linking the two N atoms. Two intra-molecular O-H⋯N hydrogen bonds were observed. In the crystal, non-classical inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis. The crystal studied was a racemic twin. ...[more]

PMID: 21587614

Similar Datasets

4,4'-Dichloro-3,3',5,5'-tetra-methyl-2,2'-[(3aR,7aR/3aS,7aS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl)bis-(methyl-ene)]diphenol.

Project description:In the title compound, C(25)H(32)Cl(2)N(2)O(2), there are two intra-molecular O-H? N hydrogen-bonding inter-actions between the hy-droxy groups on the aromatic rings and the two N atoms of the heterocyclic group. The cyclo-hexane ring adopts a chair conformation and the imidazolidine unit to which it is fused has a twisted envelope conformation. The asymmetric unit comprises one half-mol-ecule which is completed by a twofold rotation axis. A C-H?O inter-action is observed in the crystal structure.

| S-EPMC3213571 | biostudies-literature

4,4'-Diiodo-2,2'-[(3aR,7aR)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl)bis-(methyl-ene)]diphenol.

Project description:In the crystal structure of the title compound, C(21)H(24)I(2)N(2)O(2), the two N atoms of the imidazolidine moiety are linked to the hy-droxy groups by intra-molecular O-H⋯N hydrogen-bonding inter-actions. The cyclo-hexane ring adopts a chair conformation and the heterocyclic ring to which it is fused has a twisted envelope conformation.

| S-EPMC3200707 | biostudies-literature

meso-4,4'-Difluoro-2,2'-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl]bis-(methyl-ene)}diphenol.

Project description:In the crystal structure of the title compound, C(21)H(24)F(2)N(2)O(2), there are two intra-molecular O-H?N hydrogen bonds involving the N atoms of the imidazolidine ring and the hy-droxy groups. The crystal studied was a meso compound obtained by the reaction of the aminal (2S,7R,11S,16R)-1,8,10,17-tetra-aza-penta-cyclo-[8.8.1.1(8,17).0(2,7).0(11,16)]cosane with 4-fluoro-phenol. The imidazolidine ring has a twisted conformation with a CH-CH-N-CH(2) 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.

| S-EPMC3569752 | biostudies-literature

4,4'-Dibromo-2,2'-{[(3aS,7aS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl]bis-(methyl-idene)}diphenol.

Project description:The cyclo-hexane ring in the title compound, C(21)H(24)Br(2)N(2)O(2), adopts a chair conformation and the five-membered ring to which it is fused has a twisted envelope conformation. The asymmetric unit contains one half-mol-ecule, which is related to the other half by a twofold rotation axis. The two N atoms of the five-membered ring are linked to the hy-droxy groups by intra-molecular O-H?N hydrogen bonds. In the crystal, inter-molecular C-H?O and C-H?? inter-actions occur.

| S-EPMC3099886 | biostudies-other

meso-4,4'-Dimeth-oxy-2,2'-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-benz-imidazole-1,3-di-yl]bis-(methyl-ene)}diphenol.

Project description:The title compound, C23H30N2O4, a di-Mannich base derived from 4-meth-oxy-phenol and cis-1,2-di-amine-cyclo-hexane, has a perhydro-benzimidazolidine nucleus, in which the cyclo-hexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C-N-C-C torsion angles of -48.14 (15) and -14.57 (16)°. The mean plane of the heterocycle makes dihedral angles of 86.29 (6) and 78.92 (6)° with the pendant benzene rings. The mol-ecular structure of the title compound shows the presence of two inter-actions between the N atoms of the imidazolidine ring and the hydroxyl groups through intra-molecular O-H⋯N hydrogen bonds with graph-set motif S(6). The unobserved lone pairs of the N atoms are presumed to be disposed in a syn conformation, being only the second example of an exception to the typical 'rabbit-ears' effect in 1,2-di-amines.

| S-EPMC3772488 | biostudies-literature

4,4'-Dimethyl-2,2'-{[2,3,3a,4,5,6,7,7a-octa-hydro-1H-benzimidazole-1,3-di-yl]bis-(methyl-ene)}diphenol.

Project description:The asymmetric unit of the title compound, C23H30N2O2, contains one half-mol-ecule, with a twofold axis splitting the mol-ecule in two identical halves. The structure of the racemic mixture has been reported previously [Rivera et al. (2009 ▶) J. Chem. Crystallogr. 39, 827-830] but the enanti-omer reported here crystallized in the ortho-rhom-bic space group P21212 (Z = 2), whereas the racemate occurs in the triclinic space group P-1 (Z = 2). The observed mol-ecular conformation is stabilized by two intra-molecular O-H⋯N hydrogen bonds, which generate rings with graph-set motif S(6). In the crystal, mol-ecules are linked via non-classical C-H⋯O inter-actions, which stack the mol-ecules along the b axis.

| S-EPMC3772489 | biostudies-literature

4,4'-Difluoro-2,2'-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl]bis-(methyl-ene)]}diphenol.

Project description:In the crystal structure of the title compound, C(21)H(24)F(2)N(2)O(2), the two N atoms of the imidazolidine moiety are linked to the hy-droxy groups by intra-molecular O-H?N hydrogen-bonding inter-actions. The crystal studied was a racemic mixture of RR and SS enatiomers. The cyclo-hexane ring adopts a chair conformation and the imidazolidine group to which it is fused has a twisted envelope conformation.

| S-EPMC3120376 | biostudies-literature

4,4'-Dimeth-oxy-2,2'-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl-ene)}diphenol.

Project description:The title compound, C(23)H(30)N(2)O(4), is a Mannich base useful for studying the effect of an electron-donating phenol substituent on intra-molecular hydrogen bonding. In the mol-ecular structure, the cyclo-hexane ring adopts a chair conformation and the five-membered ring has a twisted envelope conformation. Each meth-oxy group is oriented in the same plane of the respective aromatic ring, showing torsion angles below 11.8 (3)° and bond angles between the meth-oxy group and the aromatic ring of 116.6 (2) and 116.6 (1)°. The structure shows inter-actions between two the N atoms of the heterocyclic ring and the hy-droxy groups by intra-molecular O-H⋯N hydrogen-bonding inter-actions. In the crystal, C-H⋯O inter-actions are observed. The crystal studied was a racemic mixture of RR and SS enanti-omers.

| S-EPMC3200725 | biostudies-literature

Benzyl 2-benzyl-4-[(3aS,7aR)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-isoindol-2-yl]-4-oxobutano-ate.

Project description:In the title compound, C(26)H(31)NO(3), the octa-hydro-1H-isoindole ring is not planar and the two rings are twisted with a C-C-C-C torsion angle of 73.6?(4)°. The six-membered ring has a chair conformation while the five-membered ring has an envelope conformation on the C-atom in position 7a. The H atoms in the 3a- and 7a-psitions are cis and the H-C-C-H torsion angle is 42.36°.

| S-EPMC3470212 | biostudies-literature

4,4'-Di-tert-butyl-2,2'-[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl)bis-(methyl-ene)]diphenol.

Project description:In the title compound, C(29)H(42)N(2)O(2), the heterocyclic ring has a twist conformation. The cyclohexane ring adopts a chair conformation. The dihedral angle between the aromatic rings is 32.74?(6)°. The mol-ecular conformation is stabilized by two intramolecular O-H?N hydrogen bonds with graph-set motif S(6). The crystal packing is stabilized by C-H?O and C-H?? inter-actions.

| S-EPMC3247337 | biostudies-literature

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