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Crystal structure and Hirshfeld surface analysis of 3-(hy-droxy-meth-yl)-3-methyl-2,6-di-phenyl-piperidin-4-one.

ABSTRACT: A new synthesis of the title compound, C₁₉H₂₁NO₂, was developed with good yield and purity using the reaction of 4-hy-droxy-3-methyl-2-butanone, benzaldehyde and ammonium acetate in glacial acetic acid as a solvent. The central piperidine ring adopts a chair conformation, and its least-squares basal plane forms dihedral angles of 85.71 (11) and 77.27 (11)° with the terminal aromatic rings. In the crystal, the mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds into double ribbons. The Hirshfeld surface analysis shows that the most important contributions are from H⋯H (68%), C⋯H/H⋯C (19%) and O⋯H/H⋯O (12%) inter-actions.

SUBMITTER: Gumus MK

PROVIDER: S-EPMC8739193 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure of 3-hy-droxy-2-(4-hy-droxy-3-meth-oxy-phenyl-methyl)-5,5-di-methyl-cyclo-hex-2-enone.

Project description:In the title compound, C16H20O4, a new starting compound for the synthesis of various heterocycles, the partially saturated six-membered ring adopts a sofa conformation. An intra-molecular O-H⋯O hydrogen bond is observed in the guaiacol residue. In the crystal, mol-ecules are assembled into a sheet structure parallel to the ab plane via O-H⋯O hydrogen bonds. The hydrogen-bond pattern is described by an R44(28) graph-set motif. The sheets are further linked by C-H⋯O hydrogen bonds into a three-dimensional network.

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Crystal structure and Hirshfeld surface analysis of 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium 2-hy-droxy-2-phenyl-acetate hemihydrate.

Project description:The asymmetric unit of the title salt, C17H17F6N2O+·C8H7O3-·0.5H2O, comprises a pair of pseudo-enanti-omeric (i.e. related by a non-crystallographic centre of symmetry) piperidin-1-ium cations, two carboxyl-ate anions and a water mol-ecule of crystallization. The cations have similar conformations approximating to a letter, L: one of them shows disorder of its -CF3 group over two sets of sites in a 0.775 (3):0.225 (3) ratio. Distinctive conformations are found for the anions, one with the carboxyl-ate group lying to one side of the plane through the phenyl ring and the other where the oxygen atoms lie to either side of the plane. In the latter, an intra-molecular hy-droxy-O-H⋯O(carboxyl-ate) charge-assisted hydrogen bond is found. The packing features extensive O-H⋯O,N hydrogen bonding, often charge-assisted; C-H⋯π inter-actions are also formed. The hydrogen bonding results in the formation of five distinctive supra-molecular synthons and assembles mol-ecules in the ac plane. The quinolinyl rings lie to either side of the layer and inter-digitate with layers on either side, are approximately parallel to the b axis and are connected by π-π [inter-centroid separation = 3.6904 (18) Å] as well as C-F⋯π(quinolin-yl) inter-actions to consolidate the three-dimensional crystal. The dominance of the conventional hydrogen bonding in the mol-ecular packing is confirmed by an analysis of the Hirshfeld surface.

| S-EPMC5095847 | biostudies-literature

Crystal structure of 2-(di-phenyl-phos-phanyl)phenyl 4-(hy-droxy-meth-yl)benzoate.

Project description:The title compound, C26H21O3P, was obtained as by-product due to the hydrolysis of the desired tosyl-ated compound. The dihedral angles between the three aromatic rings attached to the P atom lie in the range 78.1?(1)-87.6?(1)°. The hy-droxy-methyl group is disordered between two conformations in a 0.719?(9):0.281?(9) ratio. The hy-droxy H atom is not involved in inter-molecular inter-actions, while the hy-droxy O atom serves as a donor for weak C-H?O hydrogen bonds, which link the mol-ecules into chains propagating in [0-11].

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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.

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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 methyl 3,5-di-methyl-benzoate, 3,5-bis-(bromo-meth-yl)phenyl acetate and 5-hy-droxy-benzene-1,3-dicarbaldehyde.

Project description:The crystal structures of the title compounds, methyl 3,5-di-methyl-benzoate (C10H12O2; 1), 3,5-bis-(bromo-meth-yl)phenyl acetate (C10H10Br2O2; 2) and 5-hy-droxy-benzene-1,3-dicarbaldehyde (C8H6O3; 3) were determined by single-crystal X-ray analysis. The crystals of 1 are composed of strands of C-H⋯O=C bonded mol-ecules, which are further arranged into layers. As a result of the presence of two bromo-methyl substituents in compound 2, mol-ecular dimers formed by crystallographically non-equivalent mol-ecules are connected to structurally different two-dimensional aggregates in which the bromine atoms participate in Br⋯Br bonds of type I and type II. In the case of compound 3, which possesses three donor/acceptor substituents, the mol-ecular association in the crystal creates a close three-dimensional network comprising Car-yl-H⋯Ohy-droxy, Cform-yl-H⋯Oform-yl and O-H⋯Oform-yl bonds.

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Crystal structure of 2,6-bis-(2-hy-droxy-5-methyl-phen-yl)-4-phenyl-pyridinium bromide di-chloro-methane hemisolvate hemihydrate.

Project description:The asymmetric unit in the structure of the title compound, C25H22NO2 (+)·Br (-)·0.5CH2Cl2·0.5H2O, comprises two pseudosymmetry-related cations, two bromide anions, a di-chloro-methane molecule and a water mol-ecule of solvation. The two independent cations are conformationally similar with the comparative dihedral angles between the central pyridine ring and the three benzene substituent rings being 3.0?(2), 36.4?(1) and 24.2?(1)°, and 3.7?(2), 36.5?(1) and 24.8?(1)°, respectively. In the crystal, the cations, anions and water mol-ecules are linked through O-H?O and O-H?Br hydrogen bonds, forming an insular unit. Within the cations there are also intra-molecular N-H?O hydrogen bonds. Adjacent centrosymmetrically related aggregates are linked by ?-? stacking inter-actions between the pyridine ring and a benzene ring in both cations [ring-centroid separations = 3.525?(3) and 3.668?(3)?Å], forming chains extending across the ac diagonal. Voids between these chains are filled by dichloromethane molecules.

| S-EPMC4719919 | biostudies-literature

2-[Hy-droxy(2-meth-oxy-phenyl)methyl]acrylonitrile.

Project description:In the title compound, C(11)H(11)NO(2), the mean planes formed by the benzene ring and the C and N atoms of the acryl group are almost orthogonal to each other, with a dihedral angle of 85.7 (1)°. During the structure analysis, it was observed that the unit cell contains large accessible voids, with a volume of 186.9 Å(3), which may host disordered solvent mol-ecules. This affects the diffraction pattern, mostly at low scattering angles. Density identified in these solvent-accessible areas was calculated and corrected for using the SQUEEZE routine in PLATON [Spek (2009 ▶), Acta Cryst. D65, 148-155]. Despite the presence of the hy-droxy group in the mol-ecule, no classical or nonclassical hydrogen bonds are observed in the structure. This may reflect the fact that the O-H group points towards the solvent-accessible void.

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Crystal structure and Hirshfeld surface analysis of 4-(3-meth-oxy-phen-yl)-2,6-di-phenyl-pyridine.

Project description:The title compound, C24H19NO, was obtained via the reaction of (1E,2E)-3-(3-meth-oxy-phen-yl)-1-phenyl-prop-2-en-1-one with ethyl 2-oxo-propano-ate, using NH4I as a catalyst. The compound crystallizes in the monoclinic space group I2/a. In the mol-ecule, the four rings are not in the same plane, the pyridine ring being inclined to the benzene rings by 17.26 (6), 56.16 (3) and 24.50 (6)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions into a three-dimensional network. To further analyse the inter-molecular inter-actions, a Hirshfeld surface analysis was performed. Hirshfeld surface analysis indicates that the most abundant contributions to the crystal packing are from H⋯H (50.4%), C⋯H/H⋯C (37.9%) and O⋯H/H⋯O (5.1%) inter-actions.

| S-EPMC9443808 | biostudies-literature

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