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6-Formyl-2-naphthyl cis-1,5,7-trimethyl-2,4-dioxo-3-aza-bicyclo-[3.3.1]nonane-7-carboxyl-ate.

ABSTRACT: In the title compound, C(23)H(23)NO(5), the C(5)N ring adopts an envelope conformation with a C atom as the flap, whilst the saturated C(6) ring fused to it adopts a chair conformation. In the crystal, inversion dimers linked by pairs of N-H?O hydrogen bonds generate R(2) (2)(8) loops.

SUBMITTER: Xu SG

PROVIDER: S-EPMC2980281 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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6-Formyl-2-naphthyl cis-1,5,7-trimethyl-2,4-dioxo-3-aza-bicyclo-[3.3.1]nonane-7-carboxyl-ate.

Xu Sheng-Guang SG Wang Chun-Hua CH Liu Jun-Shen JS Liu Xi-Guang XG Li Long L

Acta crystallographica. Section E, Structure reports online 20091224 Pt 1

In the title compound, C(23)H(23)NO(5), the C(5)N ring adopts an envelope conformation with a C atom as the flap, whilst the saturated C(6) ring fused to it adopts a chair conformation. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops. ...[more]

PMID: 21580126

Similar Datasets

Crystal structures and supra-molecular features of 9,9-dimethyl-3,7-di-aza-bicyclo-[3.3.1]nonane-2,4,6,8-tetra-one, 3,7-di-aza-spiro-[bi-cyclo-[3.3.1]nonane-9,1'-cyclo-penta-ne]-2,4,6,8-tetra-one and 9-methyl-9-phenyl-3,7-di-aza-bicyclo-[3.3.1]nonane-2,4,6,8-tetra-one di-methyl-formamide monosolvate.

Project description:Compounds (I), C9H10N2O4, (II), C11H12N2O4, and (III), C14H12N2O4·C3H7NO represent 9,9-disubstituted-3,7-di-aza-bicyclo-[3.3.1]nonane-2,4,6,8-tetra-one deriv-atives with very similar mol-ecular geometries for the bicyclic framework: the dihedral angle between the planes of the imide groups is 74.87 (6), 73.86 (3) and 74.83 (6)° in (I)-(III), respectively. The dimethyl derivative (I) is positioned on a crystallographic twofold axis and its overall geometry deviates only slightly from idealized C2v symmetry. The spiro-cyclo-pentane derivative (II) and the phen-yl/methyl analog (III) retain only inter-nal Cs symmetry, which in the case of (II) coincides with crystallographic mirror symmetry. The cyclo-pentane moiety in (II) adopts an envelope conformation, with the spiro C atom deviating from the mean plane of the rest of the ring by 0.548 (2) Å. In compound (III), an N-H⋯O hydrogen bond is formed with the di-methyl-formamide solvent mol-ecule. In the crystal, both (I) and (II) form similar zigzag hydrogen-bonded ribbons through double inter-molecular N-H⋯O hydrogen bonds. However, whereas in (I) the ribbons are formed by two trans-arranged O=C-N-H amide fragments, the amide fragments are cis-positioned in (II). The formation of ribbons in (III) is apparently disrupted by participation of one of its N-H groups in hydrogen bonding with the solvent mol-ecule. As a result, the mol-ecules of (III) form zigzag chains rather than the ribbons through inter-molecular N-H⋯O hydrogen bonds. The crystal of (I) was a pseudo-merohedral twin.

| S-EPMC5499299 | biostudies-literature

2,4-Bis(4-propoxyphen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:In the title compound, C(26)H(33)NO(3), a crystallographic mirror plane bis-ects the mol-ecule (two C atoms, one O atom and one N atom lie on the mirror plane). The mol-ecule exists in a twin-chair conformation with equatorial orientations of the 4-propoxyphenyl groups. The dihedral angle between the 4-propoxyphenyl groups is 31.58 (3)°.

| S-EPMC3099911 | biostudies-literature

rac-4,8-Divinyl-bicyclo-[3.3.1]nonane-2,6-dione.

Project description:The title compound, C(13)H(16)O(2), is a chiral bicyclic structure composed of two fused cyclo-hexa-ne rings possessing both boat and chair conformations. The mol-ecules are packed in enantio-pure columns which are pairwise linked forming an overall racemic solid; within the column pairs the packing is governed by weak dipole-dipole inter-actions stemming from stacked carbonyl functionalities (CO(centroid)-CO(centroid) distance = 3.290?Å).

| S-EPMC2969760 | biostudies-literature

2,4-Bis(3-methoxy-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:In the crystal structure, the title compound, C(22)H(25)NO(3), exists in a twin-chair conformation with equatorial orientations of the meta-methoxy-phenyl groups on both sides of the secondary amino group. The title compound is a positional isomer of 2,4-bis-(2-methoxy-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one and 2,4-bis-(4-methoxy-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one, which both also exhibit twin-chair conformations with equatorial dispositions of the anisyl rings on both sides of the secondary amino group. In the title compound, the meta-methoxy-phenyl rings are orientated at an angle of 25.02?(3)° with respect to each other, whereas in the ortho and para isomers, the anisyl rings are orientated at dihedral angles of 33.86?(3) and 37.43?(4)°, respectively. The crystal packing is dominated by van der Waals inter-actions and by an inter-molecular N-H?O hydrogen bond, whereas in the ortho isomer, an inter-molecular N-H?? inter-action (H?Cg = 2.75?Å) is found.

| S-EPMC2980113 | biostudies-literature

2,4-Bis(2-chloro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:The mol-ecular structure of the title compound, C(20)H(19)Cl(2)NO, reveals chair conformations for both six-membered rings of the bicyclic system. Both 2-chloro-phenyl groups adopt equatorial dispositions with the chloro substituents oriented towards the carbonyl group; the aryl groups are orientated at an angle of 28.64?(3)° with respect to each other.

| S-EPMC2962203 | biostudies-literature

2,4-Bis(2-fluoro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:The title compound, C(20)H(19)F(2)NO, exists in a twin-chair conformation with an equatorial orientation of the two 2-fluoro-phenyl groups on both sides of the secondary amine group. The benzene rings are orientated at an angle of 25.68?(4)° with respect to one another and the F atoms point upwards (towards the carbonyl group). The crystal is stabilized by an inter-molecular N-H?? inter-action.

| S-EPMC2969275 | biostudies-literature

2,4-Bis(3-fluoro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:The title compound, C(20)H(19)F(2)NO, exhibits a chair-chair conformation, with the aryl groups in the heterocycle in equatorial orientations and oriented at an angle of 33.35?(3)° to one another. A crystallographic mirror plane, passing through the N atom, the C and O atoms of the carbonyl group and the C atom in the 7-position, bis-ects the mol-ecule. The mol-ecular structure is stabilized by one C-H?N inter-action and the crystal structure is stabilized by a weak C-H?? inter-action.

| S-EPMC2960516 | biostudies-literature

2,4-Bis(4-fluoro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:In the title compound, C(20)H(19)F(2)NO, a crystallographic mirror plane bis-ects the mol-ecule, passing through the N, O and two C atoms of the central ring system. The mol-ecule exists in a twin-chair conformation with equatorial dispositions of the 4-fluoro-phenyl groups on both sides of the secondary amino groups; the dihedral angle between the aromatic ring planes is 28.67?(3)°.

| S-EPMC2960654 | biostudies-literature

2,4-Bis(4-bromo-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:The title compound, C(20)H(19)Br(2)NO, shows a chair-chair conformation for the aza-bicycle with an equatorial disposition of the 4-bromo-phenyl groups [dihedral angle between the aromatic rings = 16.48?(3)°]. In the crystal, a short Br?Br contact [3.520?(4)?Å] occurs and the structure is further stabilized by N-H?O hydrogen bonds and C-H?O inter-actions.

| S-EPMC2969662 | biostudies-literature

2,4-Bis(4-chloro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:In the mol-ecular structure of the title compound, C(20)H(19)Cl(2)NO, the mol-ecule exists in a twin-chair conformation with equatorial dispositions of the 4-chloro-phenyl groups on both sides of the secondary amino group; the dihedral angle between the aromatic ring planes is 31.33?(3)°. The crystal structure is stabilized by N-H?O inter-actions, leading to chains of molecules.

| S-EPMC2968690 | biostudies-literature

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