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

ABSTRACT: 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.

SUBMITTER: Parthiban P

PROVIDER: S-EPMC3120546 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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

Parthiban P P Ramkumar V V Park Dong Ho DH Jeong Yeon Tae YT

Acta crystallographica. Section E, Structure reports online 20110520 Pt 6

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 ...[more]

PMID: 21754845

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].

| S-EPMC3470358 | biostudies-literature

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 ?-? inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.692?(3)?Å].

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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(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-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(2-methyl-phen-yl)-3-aza-bicyclo[3.3.1]nonan-9-one O-methyl-oxime.

Project description:The mol-ecule of the title compound, C(23)H(28)N(2)O, exists in a twin-chair conformation, with equatorial orientation of the ortho-tolyl groups on both sides of the secondary amino group. The title oxime compound and its ketone precursor 2,4-bis-(2-methyl-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one exhibit similar stereochemistries, with the orientation of the o-tolyl rings almost identical in both compounds. In the title compound, the tolyl rings are at an angle of 23.77?(3)° with respect to one another; the angle in the precursor is 29.4?(1)° [Vijayalakshmi, Parthasarathi, Venkatraj & Jeyaraman (2000 ?), Acta Cryst. C56, 1240-1241]. The cyclo-hexane ring and the oxime ether are disordered over two alternative orientations, with a refined site-occupancy ratio of 0.813?(2):0.186?(4). The crystal structure of the title compound is stabilized by inter-molecular N-H?? inter-actions.

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

Project description:The title compound, C(21)H(21)Cl(2)NO, exists in a twin-chair conformation with an equatorial orientation of the 4-chloro-phenyl groups on both sides of the secondary amino group; the dihedral angle between the 4-chloro-phenyl rings is 36.58?(2)°. The crystal packing is stabilized by an inter-molecular N-H?O hydrogen bond and a weak Cl?Cl [3.4331?(9)?Å] inter-action.

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

Project description:The crystal structure of the title compound, C(23)H(27)NO(3), shows that the compound exists in a chair-chair conformation with an equatorial disposition of 2-methoxy-phenyl groups at an angle of 39.94 (3)° with respect to each other. An inter-molecular N-H⋯π inter-action is observed in the crystal packing.

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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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