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Crystal structure of 4-(prop-2-yn-yloxy)-2,2,6,6-tetra-methyl-piperidin-1-ox-yl.

ABSTRACT: The title compound, C12H20NO2, was synthesized from 4-hy-droxy-2,2,6,6-tetra-methyl-piperidin-1-oxyl (hy-droxy-TEMPO) and propargyl bromide. The six-membered ring adopts a flattened chair conformation and carries a propyn-yloxy substituent in an equatorial orientation at the 4-position. The N-O bond length of the piperidin-1-oxyl unit is 1.289?(3)?Å. In the crystal, C-H?O hydrogen bonds combine with unusual C-H?? inter-actions involving the alkyne unit as acceptor to generate a three-dimensional network.

SUBMITTER: Goswami SK

PROVIDER: S-EPMC4186184 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Crystal structure of 4-(prop-2-yn-yloxy)-2,2,6,6-tetra-methyl-piperidin-1-ox-yl.

Goswami Shailesh K SK Hanton Lyall R LR McAdam C John CJ Moratti Stephen C SC Simpson Jim J

Acta crystallographica. Section E, Structure reports online 20140809 Pt 9

The title compound, C12H20NO2, was synthesized from 4-hy-droxy-2,2,6,6-tetra-methyl-piperidin-1-oxyl (hy-droxy-TEMPO) and propargyl bromide. The six-membered ring adopts a flattened chair conformation and carries a propyn-yloxy substituent in an equatorial orientation at the 4-position. The N-O bond length of the piperidin-1-oxyl unit is 1.289 (3) Å. In the crystal, C-H⋯O hydrogen bonds combine with unusual C-H⋯π inter-actions involving the alkyne unit as acceptor to generate a three-dimensional ...[more]

PMID: 25309160

Similar Datasets

Comparison of the crystal structures of 4,4'-bis-[3-(4-methyl-piperidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl and 4,4'-bis-[3-(2,2,6,6-tetra-methyl-piperidin-1-yl)prop-1-yn-1-yl]-1,1'-biphen-yl.

Project description:As part of a comprehensive program to discover α9α10 nicotinic acetyl-choline receptor antagonists, the title compounds C30H36N2, (I), and C36H48N2, (II), were synthesized by coupling 4,4'-bis-(3-bromo-prop-1-yn-1-yl)-1,1'-biphenyl with 4-methyl-piperidine and 2,2,6,6-tetra-methyl-piperidine, respectively, in aceto-nitrile at room temperature. In compound (I), the biphenyl system has a twisted conformation with a dihedral angle of 26.57 (6)° between the two phenyl rings of the biphenyl moiety, while in compound (II), the biphenyl moiety sits on a crystallographic inversion centre so the two phenyl rings are exactly coplanar. The terminal piperidine rings in both compound (I) and compound (II) are in the chair conformation. In compound (I), the dihedral angles about the ethynyl groups between the planes of the phenyl rings and the piperidine ring N atoms are 37.16 (16) and 14.20 (17)°. In compound (II), the corresponding dihedral angles are both 61.48 (17)°. There are no noteworthy inter-molecular inter-actions in (I), but in (II) there is a small π-overlap between inversion-related mol-ecules (1 - x, 1 - y, 1 - z), with an inter-planar spacing of 3.553 (3) Å and centroid-to-centroid separation of 3.859 (4) Å.

| S-EPMC4647388 | biostudies-literature

Crystal structure of 4-({5-[(E)-(3,5-di-fluoro-phen-yl)diazen-yl]-2-hy-droxy-benzyl-idene}amino)-2,2,6,6-tetra-methyl-piperidin-1-ox-yl.

Project description:The asymmetric unit of the title compound, C22H25F2N4O2, contains two crystallographically independent mol-ecules. In one mol-ecule, the two benzene rings are oriented at a dihedral angle of 1.93 (10)° and in the other mol-ecule the corresponding dihedral angle is 7.19 (9)°. The piperidine rings in the two mol-ecules adopt a similar distorted chair conformation, and both have pseudo-mirror planes passing through the N-O bonds. An intra-molecular O-H⋯N hydrogen bond between the hy-droxy group and the imine N atom is observed in both mol-ecules. In the crystal, weak C-H⋯O and C-H⋯F hydrogen bonds, enclosing R 2 (2)(6) ring motifs, and weak π-π stacking inter-actions link the mol-ecules into a three-dimensional supra-molecular network, with centroid-to-centroid distances between the nearly parallel phenyl and benzene rings of adjacent mol-ecules of 3.975 (2) and 3.782 (2) Å.

| S-EPMC4518987 | biostudies-literature

N-(1-Acryloyl-2,2,6,6-tetra-methyl-piperidin-4-yl)acryl-amide.

Project description:The title compound, C(15)H(24)N(2)O(2), crystallizes with two unique mol-ecules, (I) and (II), in the asymmetric unit, differing in the orientation of the acryloyl units with respect to the piperidine rings. The acryl-amide units are essentially planar in both mol-ecules (r.m.s. deviations = 0.042 and 0.024?Å, respectively), as are the C(3)N chains of the acryloyl units. The carbonyl O atoms of the acryloyl systems lie significantly out of these planes, viz. by -0.171?(9)?Å for molecule (I) and by 0.33?(1)?Å for molecule (II). The acryl-amide and acryloyl planes are inclined at 68.7?(4)° and 59.8?(3)° in the two mol-ecules. The piperidine rings each adopt twist boat conformations. In the crystal, strong N-H?O hydrogen bonds link the mol-ecules into zigzag C(4) chains along b. Additional C-H?O contacts result in the formation of stacks along a.

| S-EPMC3247421 | biostudies-literature

3,5-Dibromo-4-oxo-2,2,6,6-tetra-methyl-piperidin-1-yl oxide.

Project description:In the title compound, C(9)H(14)Br(2)NO(2), the substituted ring exhibits a chair conformation. A crystallographic mirror plane, passing through the N atom, the O atoms and the C atom in the 4-position, bis-ects the mol-ecule.

| S-EPMC3238922 | biostudies-literature

Crystal structure of 4-bromo-2-[(E)-N-(2,2,6,6-tetra-methyl-piperidin-4-yl)carboximido-yl]phenol dihydrate.

Project description:In the title hydrate, C16H23BrN2O·2H2O, the organic mol-ecule features a strong intra-molecular O-H?N hydrogen bond. The piperidine ring, in addition, adopts a chair conformation with the exocyclic C-N bond in an equatorial orientation. The water molecules of crystallization are disordered (each over two sets of sites with half occupancy. In the crystal, they associate into corrugated (100) sheets of (H2O)4 tetra-mers linked by O-H?O hydrogen bonds. The organic mol-ecules, in turn, are arranged at both sides of these sheets, linked by water-piperidine O-H?N hydrogen bonds.

| S-EPMC4420100 | biostudies-literature

4,4'-Bis(prop-2-yn-yloxy)biphen-yl.

Project description:The title compound, C(18)H(14)O(2), crystallizes with one half-mol-ecule in the asymmetric unit. The mol-ecule lies on an inversion center, located at the mid-point of the central C-C bond. As a result, the benzene rings are coplanar. No classical hydrogen bonds or stacking inter-actions are observed in the crystal structure.

| S-EPMC2915354 | biostudies-literature

Crystal structure of 4,4'-bis-[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1'-biphen-yl.

Project description:The title compound, C28H32N2, (I), is one of a second generation of compounds designed and synthesized based on a very potent and selective α9α10 nicotinic acetyl-choline receptor antagonist ZZ161C {1,1'-[[1,1'-biphen-yl]-4,4'-diylbis(prop-2-yne-3,1-di-yl)]bis-(3,4-di-methyl-pyridin-1-ium) bromide}, which has shown analgesic effects in a chemotherapy-induced neuropathy animal model. Compound (I) was synthesized by the reaction of 4,4'-bis-(3-bromo-prop-1-yn-1-yl)-1,1'-biphenyl with piperidine at room temperature in aceto-nitrile. The single-crystal used for X-ray analysis was obtained by dissolving (I) in a mixture of di-chloro-methane and methanol, followed by slow evaporation of the solvent. In the crystal of (I), the biphenyl moiety has a twisted conformation, with a dihedral angle of 25.93 (4)° between the benzene rings. Both piperidine head groups in (I) are in the chair conformation and are oriented so that the N-atom lone pairs of each piperidine group point away from the central biphenyl moiety.

| S-EPMC5458311 | biostudies-literature

N-[4-(Prop-2-yn-yloxy)phen-yl]maleimide.

Project description:In the title compound, C(13)H(9)NO(3), the dihedral angle between the benzene and maleimide rings is 64.1 (2)°. In the crystal structure, mol-ecules interact via C-H⋯O inter-actions.

| S-EPMC2967977 | biostudies-literature

2,2'-Bis(prop-2-yn-yloxy)-1,1'-binaphth-yl.

Project description:In the title compound, C(26)H(18)O(2), the mol-ecule is located on a twofold rotation axis. The two naphthyl ring planes in the mol-ecule are nearly perpendicular to each other [dihedral angle = 82.42 (1)°. No classical hydrogen bonds or aromatic π-π stacking inter-actions were observed.

| S-EPMC2915361 | biostudies-literature

4-Aza-niumyl-2,2,6,6-tetra-methyl-piperidin-1-ium dinitrate.

Project description:In the crystal structure of the title salt, C9H22N2 (2+)·2NO3 (-), the piperidine ring of the dication adopts a chair conformation and the orientation of the C-NH3 bond is equatorial. The ions are linked by normal and bifurcated N-H?O hydrogen bonds in R 2 (2)(6), two R 4 (2)(8) and R 3 (4)(14) graf-set motifs, generating a three-dimensional network.

| S-EPMC4051017 | biostudies-literature

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