Dennis Awasabisah , Navamoney Arulsamy , Mason Primrose , Guoxing Lin
{"title":"Crystal structure and Hirshfeld surface analysis of [(R,S)-2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol methanol monosolvate","authors":"Dennis Awasabisah , Navamoney Arulsamy , Mason Primrose , Guoxing Lin","doi":"10.1107/S2056989025006310","DOIUrl":null,"url":null,"abstract":"<div><div>The compound [(<em>R</em>,<em>S</em>)-2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol methanol monosolvate crystallizes in the <em>I</em>4<sub>1</sub>/<em>acd</em> space group. The X-ray crystal structure determination revealed that O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds are involved in the intermolecular forces of attraction. This is supported by Hirshfeld surface analysis. The X-ray crystallographic data are supported by DFT calculations.</div></div><div><div>The title compound, C<sub>17</sub>H<sub>16</sub>F<sub>6</sub>N<sub>2</sub>O·CH<sub>3</sub>OH, is composed of a quinolinyl group and a piperidinyl group connected <em>via</em> a hydroxymethine (–CHOH) functionality. The compound, which is monosolvated by methanol, was crystallized <em>via</em> slow evaporation of a methanol solution, yielding colorless prism-like crystals. The hydroxymethine center of the compound is in the absolute <em>R</em> configuration, whereas the chiral center of the piperidinyl ring is in the <em>S</em> configuration. The conformation of the piperidinyl ring is a chair. The supramolecular architecture of the crystal is sustained by a set of hydrogen bonds: O—H⋯O, N—H⋯O and C—H⋯F. The intermolecular forces are further analyzed and confirmed by a Hirshfeld surface analysis. DFT structural data computed with the <em>ORCA</em> quantum chemistry program package using the B3LYP/def2-TZVPP basis set compare quite well with the experimental X-ray crystal structural data.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 8","pages":"Pages 718-722"},"PeriodicalIF":0.6000,"publicationDate":"2025-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Crystallographica Section E: Crystallographic Communications","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2056989025001501","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CRYSTALLOGRAPHY","Score":null,"Total":0}
引用次数: 0
Abstract
The compound [(R,S)-2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol methanol monosolvate crystallizes in the I41/acd space group. The X-ray crystal structure determination revealed that O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds are involved in the intermolecular forces of attraction. This is supported by Hirshfeld surface analysis. The X-ray crystallographic data are supported by DFT calculations.
The title compound, C17H16F6N2O·CH3OH, is composed of a quinolinyl group and a piperidinyl group connected via a hydroxymethine (–CHOH) functionality. The compound, which is monosolvated by methanol, was crystallized via slow evaporation of a methanol solution, yielding colorless prism-like crystals. The hydroxymethine center of the compound is in the absolute R configuration, whereas the chiral center of the piperidinyl ring is in the S configuration. The conformation of the piperidinyl ring is a chair. The supramolecular architecture of the crystal is sustained by a set of hydrogen bonds: O—H⋯O, N—H⋯O and C—H⋯F. The intermolecular forces are further analyzed and confirmed by a Hirshfeld surface analysis. DFT structural data computed with the ORCA quantum chemistry program package using the B3LYP/def2-TZVPP basis set compare quite well with the experimental X-ray crystal structural data.
期刊介绍:
Acta Crystallographica Section E: Crystallographic Communications is the IUCr''s open-access structural communications journal. It provides a fast, simple and easily accessible publication mechanism for crystal structure determinations of inorganic, metal-organic and organic compounds. The electronic submission, validation, refereeing and publication facilities of the journal ensure rapid and high-quality publication of fully validated structures. The primary article category is Research Communications; these are peer-reviewed articles describing one or more structure determinations with appropriate discussion of the science.