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

doi:10.1107/S2056989015003187

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)

Chemistry

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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 language	English
Pages (from-to)	o195-o196
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	3
Early online date	21 Feb 2015
DOIs	https://doi.org/10.1107/S2056989015003187
Publication status	Published - 1 Mar 2015

Bibliographical note

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

Keywords

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

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Crystal structure of ethyl (2S,20R)-10 - benzyl-3-oxo-3H-dispiro[1-benzothiophene-2,30-pyrrolidine-20,1100-indeno- [1,2-b]quinoxaline]-40-carboxylate
© 2015 Govindarajet al. Licence: Creative Commons Attribution (CC-BY) https://creativecommons.org/licenses/by/4.0
Final published version, 530 KBLicence: CC BY

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Govindaraj, J., Raja, R., Suresh, M., Raghunathan, R., SubbiahPandi, A., & Harrison, W. T. A. (Ed.) (2015). 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. Acta Crystallographica Section E: Structure Reports Online, 71(3), o195-o196. https://doi.org/10.1107/S2056989015003187

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. / Govindaraj, J.; Raja, R; Suresh, M et al.
In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 3, 01.03.2015, p. o195-o196.

Research output: Contribution to journal › Article › peer-review

Govindaraj, J, Raja, R, Suresh, M, Raghunathan, R, SubbiahPandi, A & Harrison, WTA (ed.) 2015, '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', Acta Crystallographica Section E: Structure Reports Online, vol. 71, no. 3, pp. o195-o196. https://doi.org/10.1107/S2056989015003187

Govindaraj J, Raja R, Suresh M, Raghunathan R, SubbiahPandi A, Harrison WTA, (ed.). 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. Acta Crystallographica Section E: Structure Reports Online. 2015 Mar 1;71(3):o195-o196. Epub 2015 Feb 21. doi: 10.1107/S2056989015003187

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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.",

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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.

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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

SN - 1600-5368

VL - 71

SP - o195-o196

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

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ER -

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

Bibliographical note

Keywords

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