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

Edward R.T. Tiekink; James L. Wardell

doi:10.1107/S1600536814000609

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 journal › Article › peer-review

2 Citations (Scopus)

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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 language	English
Pages (from-to)	o158-o159
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	70
Issue number	2
Early online date	18 Jan 2014
DOIs	https://doi.org/10.1107/S1600536814000609
Publication status	Published - Feb 2014

Bibliographical 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).

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

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2-(2-Amino-4-nitrophenyl)-7-nitro-4H3,1-benzoxazin-4-one
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Cite this

@article{f29a9559aba54f11a76128cc037b0ff3,

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).",

year = "2014",

month = feb,

doi = "10.1107/S1600536814000609",

language = "English",

volume = "70",

pages = "o158--o159",

journal = "Acta Crystallographica Section E: Structure Reports Online",

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "2",

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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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U2 - 10.1107/S1600536814000609

DO - 10.1107/S1600536814000609

M3 - Article

AN - SCOPUS:84893692488

SN - 1600-5368

VL - 70

SP - o158-o159

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 2

ER -

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

Abstract

Bibliographical note

Keywords

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