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

ABSTRACT: 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.

SUBMITTER: Parthiban P

PROVIDER: S-EPMC3051922 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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

Parthiban P P Ramkumar V V Jeong Yeon Tae YT

Acta crystallographica. Section E, Structure reports online 20110216 Pt 3

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. ...[more]

PMID: 21522389

Similar Datasets

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

Project description: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].

| S-EPMC3470201 | biostudies-literature

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.

| S-EPMC3588829 | biostudies-literature

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-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].

| S-EPMC3470358 | biostudies-literature

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

Project description:The mol-ecule of the title compound, C(25)H(31)NO(3), exists in a twin-chair conformation with an equatorial orientation of the 4-eth-oxy-phenyl groups, as observed for its ortho isomer [Parthiban, Ramkumar, Park & Jeong (2011b ▶), Acta Cryst. E67, o1475-o1476]. The methyl and 4-eth-oxy-phenyl groups are also equatorially oriented on the bicycle, as in the ortho analogue. In particular, although the cyclo-hexa-none ring deviates from an ideal chair, the piperidone ring is closer to an ideal chair, whereas in the ortho isomer both rings are significantly puckered and deviate from ideal chairs. The 4-eth-oxy-phenyl groups on both sides of the secondary amine group are oriented at an angle of 26.11 (3)° with respect to each other, but the 2-eth-oxy-phenyl groups in the ortho isomer are oriented by less than half this [12.41 (4)°]. In contrast to the absence of any significant inter-actions in the crystal packing of the ortho isomer, the title compound features N-H⋯O inter-actions, linking the mol-ecules along the b axis.

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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⋯π inter-action.

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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.

| S-EPMC2969662 | biostudies-literature

2,4-Bis(3-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 bicyclic system adopts a twin-chair conformation with equatorial orientations of both substituents. The dihedral angle between the aromatic rings is 43.60 (2)° with respect to each other. The crystal structure is stabilized by weak N-H⋯O and strong C-H⋯O inter-actions.

| S-EPMC2968799 | 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

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

Project description:The complete mol-ecule of the title compound, C(20)H(19)Br(2)NO, is generated by crystallographic mirror symmetry, with two C, one O and one N atom lying on the mirror plane. The compound exists in a twin-chair conformation with equatorial dispositions of the 3-bromo-phenyl groups [dihedral angle between rings = 27.37 (3)°]. The packing is stabilized by weak N-H⋯O and C-H⋯O inter-actions.

| S-EPMC2959950 | biostudies-literature

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