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Crystal structures of three 3-chloro-3-methyl-2,6-di-aryl-piperidin-4-ones.

ABSTRACT: The syntheses and crystal structure of 3-chloro-3-methyl-r-2,c-6-di-phenyl-piperidin-4-one, C₁₈H₁₈ClNO, (I), 3-chloro-3-methyl-r-2,c-6-di-p-tolyl-piperidin-4-one, C₂₀H₂₂ClNO, (II), and 3-chloro-3-methyl-r-2,c-6-bis-(4-chloro-phen-yl)piperidin-4-one, C₁₈H₁₆Cl₃NO, (III), are described. In each structure, the piperidine ring adopts a chair conformation and dihedral angles between the mean planes of the phenyl rings are 58.4?(2), 73.5?(5) and 78.6?(2)° in (I), (II) and (III), respectively. In the crystals, mol-ecules are linked into C(6) chains by weak N-H?O hydrogen bonds and C-H?? inter-actions are also observed.

SUBMITTER: Arulraj R

PROVIDER: S-EPMC5290544 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Crystal structures of three 3-chloro-3-methyl-2,6-di-aryl-piperidin-4-ones.

Arulraj R R Sivakumar S S Kaur Manpreet M Thiruvalluvar A A Jasinski Jerry P JP

Acta crystallographica. Section E, Crystallographic communications 20170106 Pt 2

The syntheses and crystal structure of 3-chloro-3-methyl-r-2,c-6-di-phenyl-piperidin-4-one, C18H18ClNO, (I), 3-chloro-3-methyl-r-2,c-6-di-p-tolyl-piperidin-4-one, C20H22ClNO, (II), and 3-chloro-3-methyl-r-2,c-6-bis-(4-chloro-phen-yl)piperidin-4-one, C18H16Cl3NO, (III), are described. In each structure, the piperidine ring adopts a chair conformation and dihedral angles be ...[more]

PMID: 28217321

Similar Datasets

Crystal structure of 2-chloro-1-(3-methyl-2,6-di-phenyl-piperidin-1-yl)ethanone.

Project description:In the title compound, C20H22ClNO, the piperidine ring has a twist-boat conformation. There is an intra-molecular C-H⋯π inter-action involving the two phenyl rings which are inclined to one another by 84.91 (7)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming helical chains along [010]. The chains are linked by C-H⋯π inter-actions, forming sheets parallel to (100).

| S-EPMC4384538 | biostudies-literature

Crystal structures of (E)-(3-ethyl-1-methyl-2,6-di-phenyl-piperidin-4-yl-idene)amino phenyl carbonate and (E)-(3-isopropyl-1-methyl-2,6-di-phenyl-piperidin-4-yl-idene)amino phenyl carbonate.

Project description:In the title compounds, C27H28N2O3, (I), and C28H30N2O3, (II), the conformation about the C=N bond is E. The piperidine rings adopt chair conformations with the attached phenyl rings almost normal to their mean planes, the dihedral angles being 85.82?(8) and 85.84?(7)° in (I), and 87.98?(12) and 86.42?(13)° in (II). The phenyl rings are inclined to one another by 52.87?(8)° in (I) and by 60.51?(14)° in (II). The main difference in the conformation of the two compounds is the angle of inclination of the phen-oxy-carbonyl ring to the piperidine ring mean plane. In (I), these two planes are almost coplanar, with a dihedral angle of 2.05?(8)°, while in (II), this angle is 45.24?(13)°. In the crystal of (I), mol-ecules are linked by C-H?O hydrogen bonds, forming inversion dimers with R 2 (2)(14) loops. The dimers are linked via C-H?? inter-actions forming a three-dimensional network. In the crystal of (II), there are no significant inter-molecular inter-actions present.

| S-EPMC4257207 | biostudies-literature

Crystal structure of 1-(2-chloro-acet-yl)-2,6-bis-(4-fluoro-phen-yl)-3,3-di-methyl-piperidin-4-one.

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Crystal structures of isomeric 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)benzene-sulfonamide, 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide.

Project description:The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)-benzene-sulfonamide (I), 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide (II) and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide (III) are described. The mol-ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The mol-ecular conformation of (II) is stabilized by intra-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The crystal structure of (I) features N-H⋯O hydrogen-bonded R22(8) loops inter-connected via C(7) chains of C-H⋯O inter-actions, forming a three-dimensional architecture. The structure also features π-π inter-actions [Cg⋯Cg = 3.6970 (14) Å]. In (II), N-H⋯O hydrogen-bonded R22(8) loops are inter-connected via π-π inter-actions [inter-centroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C(4) chains of N-H⋯O hydrogen-bonded mol-ecules running parallel to [010] are connected via C-H⋯π inter-actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset π-π inter-actions [inter-centroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.

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Crystal structures of 2,6-di-bromo-4-methyl-benzo-nitrile and 2,6-di-bromo-4-methyl-phenyl isocyanide.

Project description:In the title crystals, C8H5Br2N, which are isomorphous, the steric bulk of the methyl group causes neighboring mol-ecules to become mutually inclined. This prevents the formation of planar or nearly planar sheets, which were observed in the tri-chloro and tri-bromo analogs. Instead of CN/NC?Br contacts, tetra-meric Br?Br contacts are observed. These contacts form tetra-gonally puckered sheets parallel to (001). The CN/NC and methyl groups are grouped at the peaks and troughs. Both mol-ecules lie across crystallographic mirror planes; thus, the methyl H atoms are disordered over two sets of sites with equal occupancy. The title nitrile is a redetermination. The refinement converged at R[F2 > 2?(F2)] = 0.020, whereas the original determination [Gleason & Britton, (1976 ?). Cryst. Struct. Commun.5, 229-232] had R = 0.112.

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Crystal structure of 2-chloro-1-(3-ethyl-2,6-di-phenyl-piperidin-1-yl)ethanone.

Project description:In the racemic title compound, C21H24ClNO, the dihedral angle between the planes of the benzene rings is 86.52?(14)° and those between the benzene rings and the piperidine ring are 61.66?(14) and 86.39?(14)°. The piperidine ring adopts a twisted boat conformation. No directional inter-actions could be detected in the crystal.

| S-EPMC4384592 | biostudies-literature

Crystal structure of 2,6-bis-(2,5-di-meth-oxy-phen-yl)-3,5-di-methyl-piperidin-4-one.

Project description:In the title mol-ecule, C23H29NO5, the central piperidine ring has a chair conformation. The planes of the two benzene rings are inclined each to other at 61.7?(1)°. The crystal packing exhibits no directional inter-actions only van der Waals contacts.

| S-EPMC4257243 | biostudies-literature

Crystal structures of three substituted 3-aryl-2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-ones.

Project description:Three ring-substituted 3-aryl analogs of 2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one, namely 3-(4-meth-oxy-phen-yl)-2-phenyl-4H-1,3-benzo-thia-zin-4-one, C21H17NO2S, (I), 2-phenyl-3-[4-(tri-fluoro-meth-yl)phen-yl]-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one toluene hemisolvate, C21H14F3NOS·0.5C7H8, (II), and 3-(3-bromo-phen-yl)-2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one toluene hemisolvate, C20H14BrNOS·0.5C7H8, (III), were synthesized and their crystal structures determined. The hemisolvates differ in that in (II), the asymmetric unit comprises two molecules of the benzo-thia-zinone compound and a toluene solvent mol-ecule, whereas in (III), the unit comprises one benzo-thia-zinone mol-ecule and a half-occupancy toluene solvent mol-ecule. All crystals are of racemic mixtures of the chiral 2-C atom of the thia-zine moiety, which in all structures has a screw-boat puckering, with the puckering amplitude values within the range 0.575-0.603 Å. In all three structures, the benzene plane of the benzo-thia-zine system makes a dihedral angle in the range 78.60 (5) to 98.40 (5)° with the unsubstituted benzene plane and in the range 70.50 (1) to 121.00 (5)° with the substituted benzene plane. The CF3 substituent group in one of the mol-ecules of (II) shows positional disorder, with an occupancy ratio of 0.57 (3):0.43 (3). In the crystals of (I) and (II), weak inter-molecular C-H⋯O inter-actions are present, giving in (I), mol-ecules arranged in a plane parallel to (010), and in (II), chains along a. In addition, all three structures show weak C-H⋯π inter-actions involving various aromatic rings.

| S-EPMC4971851 | biostudies-literature

Crystal structure of 1-(2-chloro-acet-yl)-3,3-dimethyl-2,6-di-p-tolyl-piperidin-4-one.

Project description:In the title compound, C23H26ClNO2, the piperidin-4-one ring adopts a distorted boat conformation. The two p-tolyl rings are nearly normal to each other, making a dihedral angle of 83.33 (10)°. They are inclined to the mean plane of the piperidine ring by 73.2 (1) and 87.22 (9)°. In the crystal, there are no significant inter-molecular inter-actions present.

| S-EPMC4350729 | biostudies-literature

2-Chloro-1-(3,3-dimethyl-2,6-di-phenyl-piperidin-1-yl)ethanone.

Project description:In the title compound, C21H24ClNO, the piperidine ring adopts a chair conformation. The two phenyl rings are inclined to one another by 20.7?(1)°, and are inclined to the mean plane of the four planar atoms of the piperidine ring by 87.64?(10) and 70.8?(1)°. The mol-ecular structure features short intra-molecular C-H?Cl and C-H?O contacts. In the crystal, there are no significant inter-molecular inter-actions present.

| S-EPMC3884441 | biostudies-literature

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