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

ABSTRACT: The title compound, C(24)H(29)NO(3), exists in a twin-chair conformation with an equatorial orientation of the 4-eth-oxy-phenyl groups. The benzene rings are inclined to each other at an angle of 28.0?(1)°. In the crystal, weak C-H?O inter-actions link mol-ecules related by translation into chains along the b axis. The crystal packing exhibits ?-? inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.692?(3)?Å].

SUBMITTER: Park DH

PROVIDER: S-EPMC3470201 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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

Park Dong Ho DH Ramkumar V V Parthiban P P

Acta crystallographica. Section E, Structure reports online 20120905 Pt 10

The title compound, C(24)H(29)NO(3), exists in a twin-chair conformation with an equatorial orientation of the 4-eth-oxy-phenyl groups. The benzene rings are inclined to each other at an angle of 28.0 (1)°. In the crystal, weak C-H⋯O inter-actions link mol-ecules related by translation into chains along the b axis. The crystal packing exhibits π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.692 (3) Å]. ...[more]

PMID: 23125645

Similar Datasets

2,4-Bis(4-eth-oxy-phen-yl)-1-methyl-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:In the title compound, C(25)H(30)NO(3), a crystallographic mirror plane bis-ects the mol-ecule. Although it is a positional isomer of 2,4-bis(4-eth-oxy-phen-yl)-7-methyl-3-aza-bicyclo-[3.3.1]non-an-9-one [C(25)H(31)NO(3), M(r) = 393.51; Park et al. (2012c ?). Acta Cryst. E68, o779-780], its mol-ecular weight is 392.50 due to the 50:50 ratio of the methyl group at bridgehead C atoms. However, the title compound exists in the same twin-chair conformation as its 7-methyl isomer. Also, the 4-eth-oxy-phenyl groups are equatorially oriented on the bicycle as in its isomer. In the title compound, the cyclo-hexanone ring deviates from an ideal chair (total puckering amplitude Q(T) = 0.5390?Å) and the piperidone ring is closer to an ideal chair (Q(T) = 0.6064?Å). These Q(T) values are very similar to those of its isomer. Even though a center of symmetry passes through the 7-methyl analog, the benzene rings are oriented 26.11?(3)° with respect to each other, whereas the orientation is 53.10?(3)° for the title compound. The title compound exhibits inter-molecular N-H?O inter-actions [H?A = 2.25?(2)?Å, versus 2.26?(2)?Å for the analog].

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2,4-Bis(2-eth-oxy-phen-yl)-7-methyl-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:The crystal structure of the title compound, C(25)H(31)NO(3), exists in a twin-chair conformation with an equatorial orientation of the ortho-eth-oxy-phenyl groups. According to Cremer and Pople [Cremer & Pople (1975 ?), J. Am. Chem. Soc. 97, 1354-1358], both the piperidone and cyclo-hexa-none rings are significantly puckered with total puckering amplitutdes Q(T) of 0.5889?(18) and 0.554?(2)?Å, respectively. The ortho-eth-oxy-phenyl groups are located on either side of the secondary amino group and make a dihedral angle of 12.41?(4)° with respect to each other. The methyl group on the cyclo-hexa-none part occupies an exocyclic equatorial disposition. The crystal packing is stabilized by weak van der Waals inter-actions.

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

Project description:In the title compound, C(28)H(37)NO(3), a crystallographic mirror plane bis-ects the mol-ecule (one half-mol-ecule in the asymmetric unit). The title compound exists in a twin-chair conformation with an equatorial orientation of the 4-but-oxy-phenyl groups. Both sides of the secondary amino group carry the 4-but-oxy-phenyl groups at an angle of 38.54 (3)° with respect to one another.

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

Project description:The asymmetric unit of the title compound, C24H29NO3, contains two independent mol-ecules, which each exibit a twin-chair conformation with an equatorial orientation of the ortho-eth-oxy-phenyl groups but different dihedral angles [41.3?(1) and 24.1?(1)°] between the benzene rings. In the crystal, pairs of weak C-H?O hydrogen bonds link the two different independent mol-ecules into dimers.

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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.

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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.

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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)°.

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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.

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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.

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2,4-Bis(2-bromo-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)Br(2)NO, the fused six-membered heterocyclic and cyclo-hexane rings adopt a twin-chair conformation with equatorial orientations of all the substituents. Both the ortho-bromo substituents of the benzene rings are oriented towards the carbonyl group; the dihedral angle between the ring planes is 29.13 (3)°. In the crystal structure, the N-H group does not participate in any hydrogen bonds.

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