Literature DB >> 35079418

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

Mustafa Kemal Gümüş1,2, Sevgi Kansiz3, Gulzhamal Bagitovna Tulemisova2, Necmi Dege4, Eiad Saif5,6.   

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. © Gümüş et al. 2022.

Entities:  

Keywords:  4-hy­droxy-3-methyl-2-butanone; Hirshfeld surface; ammonium acetate; benzaldehyde; crystal structure; hydrogen bonding; piperidone

Year:  2022        PMID: 35079418      PMCID: PMC8739193          DOI: 10.1107/S2056989021012640

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


  7 in total

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Authors:  C O Kappe
Journal:  Eur J Med Chem       Date:  2000-12       Impact factor: 6.514

2.  Synthesis and biological activities of 2,6-diaryl-3-methyl-4-piperidone derivatives.

Authors:  Natesh Rameshkumar; Anantharaman Veena; Raju Ilavarasan; Mandaleeswaran Adiraj; Pitchaimuthu Shanmugapandiyan; Seshaiah Krishnan Sridhar
Journal:  Biol Pharm Bull       Date:  2003-02       Impact factor: 2.233

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Authors:  George M Sheldrick
Journal:  Acta Crystallogr A Found Adv       Date:  2015-01-01       Impact factor: 2.290

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Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

5.  Design, docking, and DFT investigations of 2,6-bis(3,4-dihydroxyphenyl)-3-phenethylpiperidin-4-one.

Authors:  T Sasitha; Winfred Jebaraj John
Journal:  Heliyon       Date:  2021-02-11

6.  Use of intensity quotients and differences in absolute structure refinement.

Authors:  Simon Parsons; Howard D Flack; Trixie Wagner
Journal:  Acta Crystallogr B Struct Sci Cryst Eng Mater       Date:  2013-05-17

7.  The Cambridge Structural Database.

Authors:  Colin R Groom; Ian J Bruno; Matthew P Lightfoot; Suzanna C Ward
Journal:  Acta Crystallogr B Struct Sci Cryst Eng Mater       Date:  2016-04-01
  7 in total

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