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Volume 68 
Part 12 
Pages o3460-o3461  
December 2012  

Received 15 November 2012
Accepted 19 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.094
wR = 0.271
Data-to-parameter ratio = 11.6
Details
Open access

1,4-Dihydrobenzo[g]quinoxaline-2,3-dione

aDepartment of Pharmaceutical Sciences, Faculty of Medicine and Pharmaceutical Sciences, University of Douala, BP 2701, Cameroon, and bTechnische Universität Chemnitz, Fakultät für Naturwissenschaften, Institut für Chemie, Lehrstuhl für Anorganische Chemie, Strasse der Nationen 62, 09111 Chemnitz, Germany
Correspondence e-mail: francois.eya@chemie.tu-chemnitz.de

The title compound, C12H8N2O2, was prepared by the reaction of the diethyl ester of naphthalenebis(oxamate) with tert-BuNH2. The molecule is nearly planar, with an r.m.s. deviation of 0.017 Å from the plane through all 16 non-H atoms. In the crystal, a three-dimensional network is formed, composed of layers of molecules along the b- and c-axis directions, due to the formation of intermolecular N-H...O hydrogen bonds, as well as of chains along the a-axis direction due to parallel displaced sandwich-type [pi]-[pi] interactions with average distances between the interacting molecules in the range 3.35-3.40 Å.

Related literature

For the synthesis and structure of 1,4-dihydrobenzo[g]quinoxaline-2,3-dione·3H2O, see: Oxtoby et al. (2005[Oxtoby, N. S., Blake, A. J., Champness, N. R. & Wilson, C. (2005). Chem. Eur. J. 11, 4643-4654.]). For the use of bis(oxamates) and bis(oxamidates) for complex formation, see: Pardo et al. (2008[Pardo, E., Ruiz-García, R., Lloret, F., Julve, M., Cano, J., Pasán, J., Ruiz-Pérez, J., Filali, Y., Chamoreau, L.-M. & Journaux, Y. (2008). Dalton Trans. pp. 2780-2805.]) and Abdulmalic et al. (2012[Abdulmalic, M. A., Aliabadi, A., Petr, A., Krupskaya, Y., Kataev, V., Büchner, B., Hahn, T., Kortus, J. & Rüffer, T. (2012). Dalton Trans. In the press. doi:10.1039/C2DT31802D.]); Rüffer et al. (2012[Rüffer, T., Abdulmalic, M. A., Aliabadi, A., Petr, A. & Kataev, V. (2012). Dalton Trans. Accepted. doi: 10.1039/C2DT32259E.]), respectively. For the general synthesis of bis(oxamidates), see: Ruiz et al. (1997[Ruiz, R., Surville-Barland, C., Aukauloo, A., Anxolabehere-Mallart, E., Journaux, Y., Cano, J. & Muñoz, M. C. (1997). J. Chem. Soc. Dalton Trans. pp. 745-752.]) and for the synthesis of diethyl N,N'-naphtalene-bis(oxamate), see: Rüffer et al. (2007[Rüffer, T., Bräuer, B., Powell, A. K., Hewitt, I. & Salvan, G. (2007). Inorg. Chim. Acta, 360, 3475-3483.]). For thin film formation by bis(oxamato) complexes, see: Eya'ane Meva (2009[Eya'ane Meva, F. (2009). PhD thesis, Chemnitz University of Technology, Chemnitz, Germany.]); Bräuer et al. (2006[Bräuer, B., Zahn, D. R. T., Rüffer, T. & Salvan, G. (2006). Chem. Phys. Lett. 432, 226-229.]). For self-organization in supramolecular chemistry due to intermolecular [pi] interactions and/or hydrogen bonds, see: Burrow et al. (1996[Burrow, A. D., Mingos, D. M. P., White, A. J. P. & Williams, D. J. (1996). Chem. Commun. pp. 97-99.]); Chowdhry et al. (1996[Chowdhry, M. M., Mingos, D. M. P., White, A. J. P. & Williams, D. J. (1996). Chem. Commun. pp. 899-900.]); Dai et al. (1997[Dai, J., Yamamoto, M., Kudora-Sowa, T., Meakawa, M., Suenaga, Y. & Munakata, M. (1997). Inorg. Chem. 36, 2688-2690.]); Munoz et al. (1998[Munoz, M. C., Ruiz, R., Traianidis, M., Aukauloo, A., Cano, J., Journaux, Y., Fernandez, I. & Pedro, J. R. (1998). Angew. Chem. 110, 1933-1936.]). For dione tautomerism in the solid state, see: Svenson (1976[Svenson, C. (1976). Acta Chem. Scand. Ser. B, 30, 581-584.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8N2O2

  • Mr = 212.20

  • Monoclinic, P 21 /n

  • a = 7.1334 (15) Å

  • b = 8.4229 (18) Å

  • c = 15.292 (2) Å

  • [beta] = 99.792 (14)°

  • V = 905.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.1 mm

Data collection
  • Oxford Gemini S diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.649, Tmax = 1.000

  • 5294 measured reflections

  • 1773 independent reflections

  • 875 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.094

  • wR(F2) = 0.271

  • S = 0.92

  • 1773 reflections

  • 153 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.77 e Å-3

  • [Delta][rho]min = -0.57 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.91 (4) 2.27 (4) 2.866 (3) 122 (3)
N2-H2N...O2ii 0.94 (4) 1.90 (4) 2.843 (4) 176 (4)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]; (ii) -x, -y-1, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5284 ).


Acknowledgements

FEM and MAA are grateful to the DAAD for PhD research fellowships and the DFG research unit "Towards Molecular Spintronics" FOR 1154 for providing fellowships. The authors express sincere thanks to the CIM, WUS, and the Faculty of Medicine and Pharmaceutical Sciences of the University of Douala for financial support.

References

Abdulmalic, M. A., Aliabadi, A., Petr, A., Krupskaya, Y., Kataev, V., Büchner, B., Hahn, T., Kortus, J. & Rüffer, T. (2012). Dalton Trans. In the press. doi:10.1039/C2DT31802D.
Bräuer, B., Zahn, D. R. T., Rüffer, T. & Salvan, G. (2006). Chem. Phys. Lett. 432, 226-229.
Burrow, A. D., Mingos, D. M. P., White, A. J. P. & Williams, D. J. (1996). Chem. Commun. pp. 97-99.
Chowdhry, M. M., Mingos, D. M. P., White, A. J. P. & Williams, D. J. (1996). Chem. Commun. pp. 899-900.  [CrossRef]
Dai, J., Yamamoto, M., Kudora-Sowa, T., Meakawa, M., Suenaga, Y. & Munakata, M. (1997). Inorg. Chem. 36, 2688-2690.  [CrossRef] [ChemPort] [ISI]
Eya'ane Meva, F. (2009). PhD thesis, Chemnitz University of Technology, Chemnitz, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Munoz, M. C., Ruiz, R., Traianidis, M., Aukauloo, A., Cano, J., Journaux, Y., Fernandez, I. & Pedro, J. R. (1998). Angew. Chem. 110, 1933-1936.
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Oxtoby, N. S., Blake, A. J., Champness, N. R. & Wilson, C. (2005). Chem. Eur. J. 11, 4643-4654.  [CSD] [CrossRef] [PubMed] [ChemPort]
Pardo, E., Ruiz-García, R., Lloret, F., Julve, M., Cano, J., Pasán, J., Ruiz-Pérez, J., Filali, Y., Chamoreau, L.-M. & Journaux, Y. (2008). Dalton Trans. pp. 2780-2805.  [CrossRef]
Rüffer, T., Abdulmalic, M. A., Aliabadi, A., Petr, A. & Kataev, V. (2012). Dalton Trans. Accepted. doi: 10.1039/C2DT32259E.
Rüffer, T., Bräuer, B., Powell, A. K., Hewitt, I. & Salvan, G. (2007). Inorg. Chim. Acta, 360, 3475-3483.
Ruiz, R., Surville-Barland, C., Aukauloo, A., Anxolabehere-Mallart, E., Journaux, Y., Cano, J. & Muñoz, M. C. (1997). J. Chem. Soc. Dalton Trans. pp. 745-752.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Svenson, C. (1976). Acta Chem. Scand. Ser. B, 30, 581-584.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3460-o3461   [ doi:10.1107/S1600536812047526 ]

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