Literature DB >> 33953945

Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy-droxy-phen-yl)-3,3,6,6-tetra-methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca-hydro-acridin-10-yl]acetate.

Omyma A A Abd Allah1, Manpreet Kaur2, Mehmet Akkurt3, Shaaban K Mohamed4,5, Jerry P Jasinski2, Sahar M I Elgarhy6.   

Abstract

In the title compound, C27H33NO5, a 3,3,6,6-tetra-methyl-tetra-hydro-acridine-1,8-dione ring system carries an ethyl acetate substituent on the acridine N atom and an o-hy-droxy-phenyl ring on the central methine C atom of the di-hydro-pyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 80.45 (7)° and this conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond between the hy-droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. The ester C=O oxygen atom is disordered over major and minor orientations in a 0.777 (9):0.223 (9) ratio and the terminal -CH3 unit of the ethyl side chain is disordered over two sets of sites in a 0.725 (5): 0.275 (5) ratio. In the crystal, C-H⋯O hydrogen bonds combine to link the mol-ecules into a three-dimensional network. van der Waals H⋯H contacts contribute the most to the Hirshfeld surface (66.9%) followed by O⋯H/H⋯O (22.1%) contacts associated with weak hydrogen bonds. © Allah et al. 2021.

Entities:  

Keywords:  3,3,6,6-tetra­methyl­tetra­hydro­acridine-1,8-dione; C—H⋯O hydrogen bonds; O—H⋯O hydrogen bonds; acridines; crystal structure

Year:  2021        PMID: 33953945      PMCID: PMC8061104          DOI: 10.1107/S2056989021001341

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


  8 in total

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Authors:  Grzegorz Cholewiński; Krystyna Dzierzbicka; Aleksander M Kołodziejczyk
Journal:  Pharmacol Rep       Date:  2011       Impact factor: 3.024

2.  Bernthsen synthesis, antimicrobial activities and cytotoxicity of acridine derivatives.

Authors:  Mehul M Patel; Mimansha D Mali; Saurabh K Patel
Journal:  Bioorg Med Chem Lett       Date:  2010-06-04       Impact factor: 2.823

3.  9-(5-Bromo-2-hy-droxy-phen-yl)-10-(2-hy-droxy-prop-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Authors:  Ali N Khalilov; Antar A Abdelhamid; Atash V Gurbanov; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-16

4.  10-(2-Hy-droxy-eth-yl)-9-(2-hy-droxy-phen-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Authors:  Antar A Abdelhamid; Shaaban K Mohamed; Ali N Khalilov; Atash V Gurbanov; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-26

5.  Acridine and acridinones: old and new structures with antimalarial activity.

Authors:  Aymé Fernández-Calienes Valdés
Journal:  Open Med Chem J       Date:  2011-03-09

6.  SHELXT - integrated space-group and crystal-structure determination.

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

7.  Crystal structure of 9-(3-bromo-5-chloro-2-hydroxy-phen-yl)-10-(2-hy-droxy-eth-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione.

Authors:  Antar A Abdelhamid; Shaaban K Mohamed; Jim Simpson
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-07-19

8.  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
  8 in total
  1 in total

1.  Crystal structure, Hirshfeld surface and frontier mol-ecular orbital analysis of 10-benzyl-9-(4-hydroxy-3-meth-oxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione.

Authors:  V Sughanya; B Loganathan; D Praveenkumar; J Ayyappan; M L Sundararajan; A Prabhakaran; A Dhandapani; N Suresh Babu
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-07-14
  1 in total

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