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Crystal structure of the adduct (4-chloro-phen-yl)(4-hy-droxy-piperidin-1-yl)methanone-(4-chloro-phen-yl)(piperidin-1-yl)methanone (0.75/0.25).

ABSTRACT: In the title compound, 0.75C12H14ClNO2·0.25C12H14ClNO, which is an adduct comprising 0.75 4-hy-droxy-piperidin-1-yl or 0.25 4-piperidin-1-yl substituents on a common (4-chloro-phen-yl)methanone component; the dihedral angles between the benzene ring and the two piperidine rings are 51.6?(3) and 89.5?(7)°, respectively. The hy-droxy-piperidine ring is in a bis-ectional oriention (bi) with the phenyl ring. In the crystal, inter-molecular O-H?O hydrogen bonds between the hy-droxy-piperidine group and the keto O atom lead to the formation of chains extending along the c- axis direction.

SUBMITTER: Revathi BK

PROVIDER: S-EPMC4645011 | BioStudies | 2015-01-01

REPOSITORIES: biostudies

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[2-Chloro-3-nitro-5-(tri-fluoro-meth-yl)phen-yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo-thia-zinone synthesis.

Project description:1,3-Benzo-thia-zin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(tri-fluoro-meth-yl)phen-yl](piper-id-in-1-yl)methanone, C13H12ClF3N2O3, occurs as a side product as a result of competitive reaction pathways in the nucleophilic attack during the synthesis of the BTZ 8-nitro-2-(piperidin-1-yl)-6-(tri-fluoro-meth-yl)-1,3-benzo-thia-zin-4-one, following the original synthetic route, whereby the corresponding benzoyl iso-thio-cyanate is reacted with piperidine as secondary amine. In the title compound, the nitro group and the nearly planar amide group are significantly twisted out of the plane of the benzene ring. The piperidine ring adopts a chair conformation. The tri-fluoro-methyl group exhibits slight rotational disorder with a refined ratio of occupancies of 0.972?(2):0.028?(2). There is structural evidence for inter-molecular weak C-H?O hydrogen bonds.

2020-01-01 | S-EPMC7472761 | BioStudies

Paliperidonium nitrate.

Project description:In the title mol-ecular salt (systematic name: 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]eth-yl}-9-hy-droxy-2-methyl-1,6,7,8,9,9a-hexa-hydro-pyrido[1,2-a]pyrimidin-4-one nitrate), C(23)H(29)FN(4)O(3) (+)·NO(3) (-), the piperidine ring displays a chair conformation and its N atom is protonated; the N-H bond is in an axial orientation. The ring bearing the hy-droxy group exhibits a half-chair conformation. The hy-droxy group as well as the adjacent methyl-ene group are disordered over two sets of sites in a 0.823?(5):0.177?(5) ratio. In the crystal, O-H?N, O-H?O, N-H?O and N-H?N hydrogen bonds connect the components into a three-dimensional network.

2012-01-01 | S-EPMC3470306 | BioStudies

Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy-droxy-1-phenyl-eth-yl]piperidin-4-one and 8-[(1S)-1-phenyl-eth-yl]-1,4-dioxa-8-aza-spiro-[4.5]decane-7-thione.

Project description:The crystal structures of the two title piperidine derivatives show different conformations for the six-membered heterocycle. The N-substituted 4-piperidinone 1-[(1R)-2-hy-droxy-1-phenyl-eth-yl]piperidin-4-one, C13H17NO2, (I), has a chair conformation, while the piperidine substituted in position 2 with a thio-carbonyl group, 8-[(1S)-1-phenyl-eth-yl]-1,4-dioxa-8-aza-spiro-[4.5]decane-7-thione, C15H19NO2S, (II), features a half-chair conformation. Comparison of the two structures, and data retrieved from the literature, suggests that the conformational flexibility is mainly related to the hybridization state of the C atom ? to the piperidinic N atom: a Csp (3) atom favours the chair conformer, while a Csp (2) atom distorts the ring towards a half-chair conformer. In the crystal structure of (I), weak C-H?O hydrogen bonds link the mol-ecules into supra-molecular chains propagating along the b-axis direction. In the crystal of (II), the mol-ecules are linked by weak C-H?S contacts into supra-molecular chains propagating along the b-axis direction.

1000-01-01 | S-EPMC4647425 | BioStudies

3-(4-Chloro-benzo-yl)-4-(4-chloro-phen-yl)-1-phenethyl-piperidin-4-ol.

Project description:In the title compound, C(26)H(25)Cl(2)NO(2), the piperidine ring adopts a chair conformation with a cis configuration of the carbonyl and hy-droxy substituents. The dihedral angle between the aromatic rings of the chloro-benzene groups is 24.3?(2)°. The phenyl ring forms dihedral angles of 59.4?(3) and 44.1?(3)° with the benzene rings. In the crystal, mol-ecules are linked by inter-molecular O-H?N and C-H?O hydrogen bonds and C-H?? inter-actions into layers parallel to the bc plane.

1000-01-01 | S-EPMC3120371 | BioStudies

4-{[4-(Hy-droxy-meth-yl)piperidin-1-yl]meth-yl}phenol.

Project description:In the title compound, C(13)H(19)NO(2), the piperidine ring has a chair conformation with the exocyclic N-C bond in an equatorial position. In the crystal, mol-ecules are linked head-to-tail by phenol O-H?O hydrogen bonds to hy-droxy-methyl-ene O-atom acceptors, forming chains which extend along [100]. These chains form two-dimensional networks lying parallel to (101) through cyclic hydrogen-bonding associations [graph set R(4) (4)(30)], involving hy-droxy O-H donors and piperidine N-atom acceptors.

1000-01-01 | S-EPMC3394056 | BioStudies

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

Project description: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.

2014-01-01 | S-EPMC4186184 | BioStudies

2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol.

Project description:In the title compound, C22H21N3O2, the pyrimidine ring is essentially planar [maximum deviation = 0.018?(2)?Å] and forms dihedral angles of 22.70?(8) and 0.97?(7)°, respectively, with the fused benzene ring and the hy-droxy-substituted benzene ring. The piperidine ring has a chair conformation and the pyran ring has a flattened twist-boat conformation. The hy-droxy group was refined as disordered over two sets of sites in a 0.702?(4):0.298?(4) ratio. The disorder corresponds to a rotation of approxomiately 180° about the C-C bond connecting the phenol group to the pyrimidine ring and hence, both the major and minor components of disorder form intra-molecular O-H?N hydrogen bonds. In the crystal, pairs of weak C-H?? inter-actions form inversion dimers. In addition, ?-? inter-actions are observed between the pyrimidine ring and the hy-droxy-substituted benzene ring [centroid-centroid separation = 3.739?(2)?Å].

1000-01-01 | S-EPMC3998607 | BioStudies

1-(Piperidin-1-yl)-3-(2,4,6-trimethyl-phen-yl)propan-2-ol.

Project description:The title compound, C(17)H(27)NO, features a bufferfly-shaped substituted 2-propanol having an aromatic ring on the 1-carbon and a piperidine ring on the 3-carbon. The piperidine ring adopts a chair conformation and its N atom shows a trigonal coordination. In the crystal, the hy-droxy group inter-acts with the N atom of an inversion-related mol-ecule, generating an O-H?N hydrogen-bonded dimer.

1000-01-01 | S-EPMC3052162 | BioStudies

Racemic mefloquinium chloro-difluoro-acetate: crystal structure and Hirshfeld surface analysis.

Project description:In the racemic title mol-ecular salt, C17H17F6N2O+·C2ClF2O3- (systematic name: 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium chloro-difluoro-acetate), the cation, which is protonated at the piperidine N atom, has the shape of the letter, L, with the piperidin-1-ium group being approximately orthogonal to the quinolinyl residue [the Cq-Cm-Cm-Na (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79?(18)°]. An intra-molecular, charge-assisted ammonium-N-H?O(hydrox-yl) hydrogen bond ensures the hy-droxy-O and ammonium-N atoms lie to the same side of the mol-ecule [Oh-Cm-Cm-Na (h = hydrox-yl) = -59.7?(2)°]. In the crystal, charge-assisted hydroxyl-O-H?O-(carboxyl-ate) and ammonium-N+-H?O-(carboxyl-ate) hydrogen bonds generate a supra-molecular chain along [010]; the chain is consolidated by C-H?O inter-actions. Links between chains to form supra-molecular layers are of the type C-Cl??(quinolinyl-C6) and the layers thus formed stack along the a-axis direction without directional inter-actions between them. The analysis of the calculated Hirshfeld surface points to the dominance of F?H contacts to the surface (40.8%) with significant contributions from F?F (10.5%) and C?F (7.0%) contacts.

1000-01-01 | S-EPMC6038619 | BioStudies

Redetermination of loperamide monohydrate.

Project description:The structure of the title compound {systematic name: 4-[4-(4-chloro-phen-yl)-4-hy-droxy-piperidin-1-yl]-N,N-dimethyl-2,2-di-phenyl-butanamide monohydrate}, C(29)H(33)ClN(2)O(2)·H(2)O, has been redetermined at 170?(2)?K. The redetermination is of significantly higher precision than the previous structure determination at room temperature and includes the H-atom coordinates that were not included in the previous report [Germain et al. (1977 ?). Acta Cryst. B33, 942-944]. It consists of a piperidin-1-yl ring in a distorted chair conformation, with the N,N-dimethyl-?,?-diphenyl-butyramide and the 4-chloro-phenyl and hy-droxy groups bonded in para positions and an external water mol-ecule within the asymmetric unit. The dihedral angles between the mean plane of the piperidine ring and the 4-chloro-phenyl and two benzene rings are 83.4?(5), 76.4?(2) and 85.9?(2)°, respectively. The two benzene rings are inclined to one another by 50.8?(6)°. In the crystal, mol-ecules are linked by O-H?O and O-H?N hydrogen bonds and weak C-H?O intermolecular interactions, forming an infinite two-dimensional network along [110].

2012-01-01 | S-EPMC3275278 | BioStudies

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