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

ABSTRACT: The heterocyclic ring in the title compound, C(27)H(34)N(2)O(6), has an envelope conformation on one of the bridgehead C atoms [Q(2) = 0.4487?(19)?Å and ? = 291.3?(2)°]. Two strong intra-molecular O-H?N hydrogen bonds stabilize the mol-ecular conformation. The benzoate groups differ in the relative orientations of the ethyl groups, as quanti-fied by the values of the C-O-C-C torsion angles of -86.5?(2) and -178.97?(17)°. The carbonyl groups are nearly coplanar with the benzene rings, forming C-C-C-O torsion angles of 0.9?(3) and 3.4?(3)°. The crystal structure is stabilized by weak inter-molecular C-H?O inter-actions.

SUBMITTER: Rivera A

PROVIDER: S-EPMC3247559 | biostudies-other | 2011 Nov

REPOSITORIES: biostudies-other

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

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

Acta crystallographica. Section E, Structure reports online 20111005 Pt 11

The heterocyclic ring in the title compound, C(27)H(34)N(2)O(6), has an envelope conformation on one of the bridgehead C atoms [Q(2) = 0.4487 (19) Å and ϕ = 291.3 (2)°]. Two strong intra-molecular O-H⋯N hydrogen bonds stabilize the mol-ecular conformation. The benzoate groups differ in the relative orientations of the ethyl groups, as quanti-fied by the values of the C-O-C-C torsion angles of -86.5 (2) and -178.97 (17)°. The carbonyl groups are nearly coplanar with the benzene rings, forming C-C ...[more]

PMID: 22219864

Similar Datasets

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

Project description:The title compound, C(25)H(30)N(2)O(6), has the imidazolidine ring in an envelope conformation. There are two intra-molecular O-H?N hydrogen-bond inter-actions with graph-set motif S(6). The cyclo-hexane ring adopts a slightly distorted chair conformation. One methyl carboxyl-ate substituent forms a dihedral angle of 12.00?(5)° with the plane of the benzene ring, while the other methyl carboxyl-ate group is almost coplanar, making a dihedral angle of 2.26?(9)°. In the crystal, pairs of inter-molecular C-H?O hydrogen bonds form racemic dimers, corresponding to an R(2) (2)(18) graph-set motif. Further weak C-H?O inter-actions generate a chain running along the c axis.

| S-EPMC3247326 | biostudies-literature

Di-n-butyl 4,4'-dihy-droxy-3,3'-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl]bis-(methyl-ene)}dibenzoate.

Project description:The complete molecule of the title compound, C(31)H(42)N(2)O(6), is generated by crystallographic twofold symmetry, with one C atom lying on the axis. The dihedral angle between the aromatic rings is 57.03?(6)°. The central heterocyclic ring adopts a half-chair conformation. The mol-ecular conformation is stabilized by two intra-molecular O-H?N hydrogen bonds with the N atoms of the heterocyclic ring as the acceptors. In the crystal, mol-ecules are linked into chains along the c axis by non-classical C-H?O hydrogen bonds.

| S-EPMC3200585 | biostudies-literature

Di-n-propyl 4,4'-dihy-droxy-3,3'-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-benzimidazole-1,3-di-yl]bis-(methyl-ene)}dibenzoate.

Project description:The title compound, C(29)H(38)N(2)O(6), was prepared as model for studying intra-molecular hydrogen-bonding inter-actions. Mol-ecules of the title compound are located on a crystallographic twofold rotation axis, which passes through the C atom linked to the two N atoms on the imidazolidine ring. The mol-ecular structure shows the existence of two intra-molecular O-H?N hydrogen-bonding inter-actions between the two N atoms of the imidazolidine moiety and the hy-droxy groups in the aromatic rings. The crystal structure shows the strain of ring fusion in the perhydro-benzimidazole moiety according to the endocyclic bond angles and the torsion angles, which evidence a puckering of the cyclo-hexane ring with respect to normal tetra-hedral bond angles in an ideal chair conformation.

| S-EPMC3201437 | biostudies-other

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'-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'-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

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

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'-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.

Project description: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.

| S-EPMC2983180 | 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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