Literature DB >> 33936756

Crystal structures of 1-(4-chloro-phen-yl)-4-(4-methyl-phen-yl)-2,5-dioxo-1,2,5,6,7,8-hexa-hydro-quinoline-3-carb-oxy-lic acid and 4-(4-meth-oxy-phen-yl)-1-(4-methyl-phen-yl)-2,5-dioxo-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbo-nitrile.

Omyma A Abd Allah1, Manpreet Kaur2, Mehmet Akkurt3, Shaaban K Mohamed4,5, Asmaa H A Tamam1, Sahar M I Elgarhy6, Jerry P Jasinski2.   

Abstract

In the title compounds C23H21ClN2O3 [I, namely 1-(4-chloro-phen-yl)-4-(4-methyl-phen-yl)-3,8-dioxo-1,2,5,6,7,8-hexa-hydro-quine-3-carb-oxy-lic acid] and C24H22N2O3 [II, namely 4-(4-meth-oxy-phen-yl)-1-(4-methyl-phen-yl)-2,5-dioxo-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbo-nitrile], each of the cyclo-hexene and di-hydro-pyridine rings of the 1,2,5,6,7,8-hexa-hydro-quinoline moieties adopts a twisted-boat conformation. The asymmetric units of both compounds I and II consist of two independent mol-ecules (A and B). In II A, three carbon atoms of the cyclo-hexene ring are disordered over two sets of sites in a 0.670 (11):0.330 (11) occupancy ratio. In the crystal of I, mol-ecules are linked through classical N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif and with their mol-ecular planes parallel to the crystallographic (020) plane. Non-classical C-H⋯O hydrogen-bonding inter-actions connect the dimers, resulting in a three-dimensional network. In the crystal of II, mol-ecules are linked by C-H⋯N, C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network. © Allah et al. 2021.

Entities:  

Keywords:  crystal structure; cyclo­hexene ring; dimer; di­hydro­pyridine ring; hexa­hydro­quinoline ring

Year:  2021        PMID: 33936756      PMCID: PMC8025871          DOI: 10.1107/S2056989021002140

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


  13 in total

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Review 4.  A review on anticancer potential of bioactive heterocycle quinoline.

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Journal:  Eur J Med Chem       Date:  2014-07-24       Impact factor: 6.514

5.  4-(4-Chloro-phen-yl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octa-hydro-quinoline-3-carbonitrile.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-14

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 refinement with SHELXL.

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

8.  Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

Authors:  Malahat M Kurbanova; Elnur Z Huseynov; Atash V Gurbanov; Abel M Maharramov; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-27

9.  8-Methyl-2-oxo-4-(thio-phen-2-yl)-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile.

Authors:  Abdullah M Asiri; Hassan M Faidallah; Alaa Anwar Ahmad Saqer; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-30

10.  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
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