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Volume 69 
Part 5 
Pages o813-o814  
May 2013  

Received 10 April 2013
Accepted 25 April 2013
Online 30 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.106
Data-to-parameter ratio = 16.3
Details
Open access

8,15-Dioxa-10,13-diazatetracyclo[14.4.0.02,7.09,14]icosa-1(16),2,4,6,9(14),10,12,17,19-nonaene

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

The asymmetric unit of the title compound, C16H10N2O2, contains one half-molecule, the complete molecule being generated by twofold rotation symmetry. The plane of the pyrazine ring forms a dihedral angle of 64.87 (6)° with that of the benzene ring, and the planes of the two benzene rings are inclined to one another by 54.20 (6)°. The O atom deviates from the plane of the benzene ring by 0.1549 (8) Å. There are no significant intermolecular interactions in the crystal.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009[Du, X. H., Gustin, D. J., Chen, X. Q., Duquette, J., McGee, L. R., Wang, Z. L., Ebsworth, K., Henne, K., Lemon, B., Ma, J., Miao, S. C., Sabalan, E., Sullivan, T. J., Tonn, G., Collins, T. L. & Medina, J. C. (2009). Bioorg. Med. Chem. Lett. 19, 5200-5204.]); Dubinina et al. (2006[Dubinina, G. G., Platonov, M. O., Golovach, S. M., Borysko, P. O., Tolmachov, A. O. & Volovenko, Y. M. (2006). Eur. J. Med. Chem. 41, 727-737.]); Ellsworth et al. (2007[Ellsworth, B. A., Wang, Y., Zhu, Y. H., Pendri, A., Gerritz, S. W., Sun, C. Q., Carlson, K. E., Kang, L. Y., Baska, R. A., Yang, Y. F., Huang, Q., Burford, N. T., Cullen, M. J., Johnghar, S., Behnia, K., Pelleymounter, M. A., Washburn, W. N. & Ewing, W. R. (2007). Bioorg. Med. Chem. Lett. 17, 3978-3982.]); Mukaiyama et al. (2007[Mukaiyama, H., Nishimura, T., Kobayashi, S., Ozawa, T., Kamada, N., Komatsu, Y., Kikuchi, S., Oonota, H. & Kusama, H. (2007). Bioorg. Med. Chem. Lett. 15, 868-885.]). For background to the fluorescence properties of related compounds, see: Kawai et al. (2001[Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23-32.]); Abdullah (2005[Abdullah, Z. (2005). Intl J. Chem. Sci. 3, 9-15.]) and for their biological activity, see: Seitz et al. (2002[Seitz, L. E., Suling, W. J. & Reynolds, R. C. (2002). J. Med. Chem. 45, 5604-5606.]); Temple et al. (1970[Temple, C. Jr, Rose, J. D. & Montgomery, J. A. (1970). J. Med. Chem. 13, 1234-1235.]). For a related structure, see: Nasir et al. (2010[Nasir, S. B., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2187.]).

[Scheme 1]

Experimental

Crystal data
  • C16H10N2O2

  • Mr = 262.26

  • Orthorhombic, P b c n

  • a = 14.429 (3) Å

  • b = 10.162 (2) Å

  • c = 8.3313 (18) Å

  • V = 1221.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.981

  • 6082 measured reflections

  • 1502 independent reflections

  • 1226 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.106

  • S = 1.03

  • 1502 reflections

  • 92 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2586 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS and DV thank the UGC (SAP-CAS) for the departmental facilties. TS also thanks the DST Inspire program for financial assistance.

References

Abdullah, Z. (2005). Intl J. Chem. Sci. 3, 9-15.  [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Du, X. H., Gustin, D. J., Chen, X. Q., Duquette, J., McGee, L. R., Wang, Z. L., Ebsworth, K., Henne, K., Lemon, B., Ma, J., Miao, S. C., Sabalan, E., Sullivan, T. J., Tonn, G., Collins, T. L. & Medina, J. C. (2009). Bioorg. Med. Chem. Lett. 19, 5200-5204.  [CrossRef] [PubMed] [ChemPort]
Dubinina, G. G., Platonov, M. O., Golovach, S. M., Borysko, P. O., Tolmachov, A. O. & Volovenko, Y. M. (2006). Eur. J. Med. Chem. 41, 727-737.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ellsworth, B. A., Wang, Y., Zhu, Y. H., Pendri, A., Gerritz, S. W., Sun, C. Q., Carlson, K. E., Kang, L. Y., Baska, R. A., Yang, Y. F., Huang, Q., Burford, N. T., Cullen, M. J., Johnghar, S., Behnia, K., Pelleymounter, M. A., Washburn, W. N. & Ewing, W. R. (2007). Bioorg. Med. Chem. Lett. 17, 3978-3982.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23-32.  [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Mukaiyama, H., Nishimura, T., Kobayashi, S., Ozawa, T., Kamada, N., Komatsu, Y., Kikuchi, S., Oonota, H. & Kusama, H. (2007). Bioorg. Med. Chem. Lett. 15, 868-885.  [ChemPort]
Nasir, S. B., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2187.  [CSD] [CrossRef] [details]
Seitz, L. E., Suling, W. J. & Reynolds, R. C. (2002). J. Med. Chem. 45, 5604-5606.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Temple, C. Jr, Rose, J. D. & Montgomery, J. A. (1970). J. Med. Chem. 13, 1234-1235.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o813-o814   [ doi:10.1107/S1600536813011318 ]

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