2-(2-Amino-4-nitrophenyl)-7-nitro-4H-3,1-benzoxazin-4-one

Edward R.T. Tiekink*, James L. Wardell

*Corresponding author for this work

    Research output: Contribution to journalArticle

    1 Citation (Scopus)
    5 Downloads (Pure)

    Abstract

    In the title compound, C14H8N4O6, the benzoxazin-4-one fused-ring system (r.m.s. deviation = 0.018Å) is coplanar with the attached benzene ring [dihedral angle = 0.81(4)°], there being an intramolecular N - HN hydrogen bond between them. Each nitro group is twisted out of the plane of the attached benzene ring [O - N - C - C torsion angles = 167.94(11) and 170.38(11)°]. In the crystal, amine-nitro N - HO hydrogen bonds lead to centrosymmetric dimeric aggregates that are connected into a three-dimensional architecture by oxazinyl-nitro C - HO and π-π interactions [inter-centroid distance between the oxazinyl and terminal benzene rings = 3.5069(7)Å].

    Original languageEnglish
    Pages (from-to)o158-o159
    Number of pages2
    JournalActa Crystallographica Section E: Structure Reports Online
    Volume70
    Issue number2
    Early online date18 Jan 2014
    DOIs
    Publication statusPublished - Feb 2014

    Fingerprint

    Benzene
    rings
    benzene
    Hydrogen bonds
    Dihedral angle
    hydrogen bonds
    Torsional stress
    Amines
    centroids
    torsion
    dihedral angle
    amines
    Crystals
    deviation
    4-nitrophenyl
    crystals
    interactions

    Keywords

    • data-to-parameter ratio = 13.4
    • mean σ(C-C) = 0.002 Å
    • R factor = 0.034
    • single-crystal X-ray study
    • T = 100 K
    • wR factor = 0.101

    ASJC Scopus subject areas

    • Chemistry(all)
    • Materials Science(all)
    • Condensed Matter Physics

    Cite this

    2-(2-Amino-4-nitrophenyl)-7-nitro-4H-3,1-benzoxazin-4-one. / Tiekink, Edward R.T.; Wardell, James L.

    In: Acta Crystallographica Section E: Structure Reports Online, Vol. 70, No. 2, 02.2014, p. o158-o159.

    Research output: Contribution to journalArticle

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    title = "2-(2-Amino-4-nitrophenyl)-7-nitro-4H-3,1-benzoxazin-4-one",
    abstract = "In the title compound, C14H8N4O6, the benzoxazin-4-one fused-ring system (r.m.s. deviation = 0.018{\AA}) is coplanar with the attached benzene ring [dihedral angle = 0.81(4)°], there being an intramolecular N - HN hydrogen bond between them. Each nitro group is twisted out of the plane of the attached benzene ring [O - N - C - C torsion angles = 167.94(11) and 170.38(11)°]. In the crystal, amine-nitro N - HO hydrogen bonds lead to centrosymmetric dimeric aggregates that are connected into a three-dimensional architecture by oxazinyl-nitro C - HO and π-π interactions [inter-centroid distance between the oxazinyl and terminal benzene rings = 3.5069(7){\AA}].",
    keywords = "data-to-parameter ratio = 13.4, mean σ(C-C) = 0.002 {\AA}, R factor = 0.034, single-crystal X-ray study, T = 100 K, wR factor = 0.101",
    author = "Tiekink, {Edward R.T.} and Wardell, {James L.}",
    note = "The use of the EPSRC X-ray crystallographic service (Coles & Gale, 2012[Coles, S. J. & Gale, P. A. (2012). Chem. Sci. 3, 683-689.]) at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Structural studies are supported by the Ministry of Higher Education (Malaysia) and the University of Malaya through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).",
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    TY - JOUR

    T1 - 2-(2-Amino-4-nitrophenyl)-7-nitro-4H-3,1-benzoxazin-4-one

    AU - Tiekink, Edward R.T.

    AU - Wardell, James L.

    N1 - The use of the EPSRC X-ray crystallographic service (Coles & Gale, 2012[Coles, S. J. & Gale, P. A. (2012). Chem. Sci. 3, 683-689.]) at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Structural studies are supported by the Ministry of Higher Education (Malaysia) and the University of Malaya through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).

    PY - 2014/2

    Y1 - 2014/2

    N2 - In the title compound, C14H8N4O6, the benzoxazin-4-one fused-ring system (r.m.s. deviation = 0.018Å) is coplanar with the attached benzene ring [dihedral angle = 0.81(4)°], there being an intramolecular N - HN hydrogen bond between them. Each nitro group is twisted out of the plane of the attached benzene ring [O - N - C - C torsion angles = 167.94(11) and 170.38(11)°]. In the crystal, amine-nitro N - HO hydrogen bonds lead to centrosymmetric dimeric aggregates that are connected into a three-dimensional architecture by oxazinyl-nitro C - HO and π-π interactions [inter-centroid distance between the oxazinyl and terminal benzene rings = 3.5069(7)Å].

    AB - In the title compound, C14H8N4O6, the benzoxazin-4-one fused-ring system (r.m.s. deviation = 0.018Å) is coplanar with the attached benzene ring [dihedral angle = 0.81(4)°], there being an intramolecular N - HN hydrogen bond between them. Each nitro group is twisted out of the plane of the attached benzene ring [O - N - C - C torsion angles = 167.94(11) and 170.38(11)°]. In the crystal, amine-nitro N - HO hydrogen bonds lead to centrosymmetric dimeric aggregates that are connected into a three-dimensional architecture by oxazinyl-nitro C - HO and π-π interactions [inter-centroid distance between the oxazinyl and terminal benzene rings = 3.5069(7)Å].

    KW - data-to-parameter ratio = 13.4

    KW - mean σ(C-C) = 0.002 Å

    KW - R factor = 0.034

    KW - single-crystal X-ray study

    KW - T = 100 K

    KW - wR factor = 0.101

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