Received 10 May 2010
aDepartment of Pharmaceutical Engineering, Biotechnology College, Tianjin University of Science & Technology (TUST), Tianjin 300457, People's Republic of China,bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cPharmaceutical Research Centre, PCSIR Labs Complex, Karachi 75280, Pakistan
Correspondence e-mail: email@example.com
The molecule of the title compound, C13H9NO2, is slightly twisted with a dihedral angle of 4.85 (9)° between the nine-membered ring system and the phenyl ring. The nine non-H atoms of the 1H-pyrrolo[2,1-c][1,4]oxazin-1-one system are coplanar [r.m.s. deviation = 0.0122 (2) Å]. In the crystal, weak intermolecular C-HO interactions link molecules into chains along . The crystal studied was an inversion twin with a 0.48624 (9):0.51376 (9) domain ratio.
For the biological activity and applications of pyrrolo[1,2-a]pyrazine derivatives, see: Bélanger et al. (1983); Fu et al. (2002); Micheli et al. (2008). For a related structure, see: Khan et al. (2010). For standard bond-length data, see: Allen et al. (1987).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2449 ).
STK acknowledges funding from the Industrial Linkage Programme of Pakistan Council of Scientific and Industrial Research (PCSIR) Laboratories, Pakistan. He also thanks Dr Song Haibin of the State Key Laboratory of Elemento-Organic Chemistry, Nankai University, for the X-ray data collection. PY is grateful to Tianjin University of Science & Technology for a research grant (No. 2009 0431).
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bélanger, P. C., Atkinson, J. G., Rooney, C. S., Britcher, S. F. & Remy, D. C. (1983). J. Org. Chem. 48, 3234-3241.
Fu, D.-C., Yu, H. & Zhang, S.-F. (2002). Chin. Chem. Lett. 13, 1051-1054.
Khan, S. T., Yu, P., Hua, E., Ali, S. N. & Nisa, M. (2010). Acta Cryst. E66, o711.
Micheli, F., Bertani, B., Bozzoli, A., Crippa, L., Cavanni, P., Di Fabio, R., Donati, D., Marzorati, P., Merlo, G., Paio, A., Perugini, L. & Zarantonello, P. (2008). Bioorg. Med. Chem. Lett. 18, 1804-1809.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.