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

ABSTRACT: The crystal structure of the title compound, C(21)H(21)F(2)NO, shows that the compound exists in a twin-chair conformation with an equatorial orientation of the ortho-fluoro-phenyl groups on either side of the secondary amino group. The title compound is a 1-methyl-ated analog of 2,4-bis-(2-fluoro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one; the two compound both exhibit the same stereochemistry but the orientation of the ortho-fluoro-phenyl rings differs slightly. In the title compound, the rings are orientated at a dihedral angle of 36.70?(3)° with respect to one another, whereas in the non-methyl analog, the angle is 25.68?(4)°. The crystal structure of the title compound is stabilized by an inter-molecular N-H?? inter-action and a weak C-H?F inter-action.

SUBMITTER: Parthiban P

PROVIDER: S-EPMC2980085 | biostudies-other | 2009

REPOSITORIES: biostudies-other

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2,4-Bis(2-fluoro-phen-yl)-1-methyl-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 20091219 Pt 1

The crystal structure of the title compound, C(21)H(21)F(2)NO, shows that the compound exists in a twin-chair conformation with an equatorial orientation of the ortho-fluoro-phenyl groups on either side of the secondary amino group. The title compound is a 1-methyl-ated analog of 2,4-bis-(2-fluoro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one; the two compound both exhibit the same stereochemistry but the orientation of the ortho-fluoro-phenyl rings differs slightly. In the title compound, the rings ...[more]

PMID: 21580078

Similar Datasets

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(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(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⋯π inter-action.

| S-EPMC2960516 | biostudies-literature

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.

| S-EPMC3009131 | biostudies-literature

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.

| S-EPMC2983554 | biostudies-literature

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.

| S-EPMC2972093 | biostudies-literature

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(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.

| S-EPMC3120546 | 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(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

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