Crystal structure of ethyl (2S,2′ R)-1′-benzyl-3-oxo-3H-dispiro[1-benzothio-phene-2,3′-pyrrolidine-2′,11″-indeno-[1,2-b]quinoxaline]-4′-carboxylate

J. Govindaraj, R Raja, M Suresh, R. Raghunathan, A. SubbiahPandi, William Thomas Alexander Harrison (Editor)

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Abstract

In the title compound, C35H27N3O3S, the spiro-linked five-membered rings both adopt twisted conformations. The pyrrolidine ring makes dihedral angles of 80.5 (1) and 77.4 (9)° with the benzothiophene ring system and the quinoxaline ring system, respectively. The S atom and C=O unit of the benzothiophene ring system are disordered over two opposite orientations in a 0.768 (4):0.232 (4) ratio. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.680 (16):0.320 (16) ratio. In the crystal, molecules are linked by C - H⋯O, C - H⋯N and π-π interactions [shortest centroid-centroid distance = 3.4145 (19) Å], resulting in a three-dimensional network.
Original languageEnglish
Pages (from-to)o195-o196
Number of pages2
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number3
Early online date21 Feb 2015
DOIs
Publication statusPublished - 1 Mar 2015

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quinoxalines
Quinoxalines
carboxylates
Spiro Compounds
Crystal structure
Atoms
crystal structure
rings
Dihedral angle
Conformations
centroids
Crystals
Molecules
atoms
dihedral angle
benzothiophene
pyrrolidine
crystals
molecules
interactions

Keywords

  • Benzothiophene
  • Biological activity
  • Crystal structure
  • Dispiro compounds
  • Ester
  • Hydrogen bonding
  • Indeno[1,2-b]quinoxaline
  • Pyrrolidine
  • π-πinteractions

Cite this

@article{1a7bf959b5bd46519c8b5c791002058b,
title = "Crystal structure of ethyl (2S,2′ R)-1′-benzyl-3-oxo-3H-dispiro[1-benzothio-phene-2,3′-pyrrolidine-2′,11″-indeno-[1,2-b]quinoxaline]-4′-carboxylate",
abstract = "In the title compound, C35H27N3O3S, the spiro-linked five-membered rings both adopt twisted conformations. The pyrrolidine ring makes dihedral angles of 80.5 (1) and 77.4 (9)° with the benzothiophene ring system and the quinoxaline ring system, respectively. The S atom and C=O unit of the benzothiophene ring system are disordered over two opposite orientations in a 0.768 (4):0.232 (4) ratio. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.680 (16):0.320 (16) ratio. In the crystal, molecules are linked by C - H⋯O, C - H⋯N and π-π interactions [shortest centroid-centroid distance = 3.4145 (19) {\AA}], resulting in a three-dimensional network.",
keywords = "Benzothiophene, Biological activity, Crystal structure, Dispiro compounds, Ester, Hydrogen bonding, Indeno[1,2-b]quinoxaline, Pyrrolidine, π-πinteractions",
author = "J. Govindaraj and R Raja and M Suresh and R. Raghunathan and A. SubbiahPandi and Harrison, {William Thomas Alexander}",
note = "The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.",
year = "2015",
month = "3",
day = "1",
doi = "10.1107/S2056989015003187",
language = "English",
volume = "71",
pages = "o195--o196",
journal = "Acta Crystallographica Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "International Union of Crystallography",
number = "3",

}

TY - JOUR

T1 - Crystal structure of ethyl (2S,2′ R)-1′-benzyl-3-oxo-3H-dispiro[1-benzothio-phene-2,3′-pyrrolidine-2′,11″-indeno-[1,2-b]quinoxaline]-4′-carboxylate

AU - Govindaraj, J.

AU - Raja, R

AU - Suresh, M

AU - Raghunathan, R.

AU - SubbiahPandi, A.

A2 - Harrison, William Thomas Alexander

N1 - The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.

PY - 2015/3/1

Y1 - 2015/3/1

N2 - In the title compound, C35H27N3O3S, the spiro-linked five-membered rings both adopt twisted conformations. The pyrrolidine ring makes dihedral angles of 80.5 (1) and 77.4 (9)° with the benzothiophene ring system and the quinoxaline ring system, respectively. The S atom and C=O unit of the benzothiophene ring system are disordered over two opposite orientations in a 0.768 (4):0.232 (4) ratio. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.680 (16):0.320 (16) ratio. In the crystal, molecules are linked by C - H⋯O, C - H⋯N and π-π interactions [shortest centroid-centroid distance = 3.4145 (19) Å], resulting in a three-dimensional network.

AB - In the title compound, C35H27N3O3S, the spiro-linked five-membered rings both adopt twisted conformations. The pyrrolidine ring makes dihedral angles of 80.5 (1) and 77.4 (9)° with the benzothiophene ring system and the quinoxaline ring system, respectively. The S atom and C=O unit of the benzothiophene ring system are disordered over two opposite orientations in a 0.768 (4):0.232 (4) ratio. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.680 (16):0.320 (16) ratio. In the crystal, molecules are linked by C - H⋯O, C - H⋯N and π-π interactions [shortest centroid-centroid distance = 3.4145 (19) Å], resulting in a three-dimensional network.

KW - Benzothiophene

KW - Biological activity

KW - Crystal structure

KW - Dispiro compounds

KW - Ester

KW - Hydrogen bonding

KW - Indeno[1,2-b]quinoxaline

KW - Pyrrolidine

KW - π-πinteractions

U2 - 10.1107/S2056989015003187

DO - 10.1107/S2056989015003187

M3 - Article

VL - 71

SP - o195-o196

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

IS - 3

ER -