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Volume 66 
Part 6 
Page o1469  
June 2010  

Received 10 May 2010
Accepted 14 May 2010
Online 26 May 2010

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Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.085
Data-to-parameter ratio = 8.3
Details
Open access

3-Phenyl-1H-pyrrolo[2,1-c][1,4]oxazin-1-one

Salman Tariq Khan,a+ Peng Yu,a* Suchada Chantrapromma,b++ Yong-En Guoa and Nighat Afzac

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: yupeng@tust.edu.cn

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-H...O interactions link molecules into chains along [1[\overline{1}]0]. The crystal studied was an inversion twin with a 0.48624 (9):0.51376 (9) domain ratio.

Related literature

For the biological activity and applications of pyrrolo[1,2-a]pyrazine derivatives, see: Bélanger et al. (1983[Bélanger, P. C., Atkinson, J. G., Rooney, C. S., Britcher, S. F. & Remy, D. C. (1983). J. Org. Chem. 48, 3234-3241.]); Fu et al. (2002[Fu, D.-C., Yu, H. & Zhang, S.-F. (2002). Chin. Chem. Lett. 13, 1051-1054.]); Micheli et al. (2008[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.]). For a related structure, see: Khan et al. (2010[Khan, S. T., Yu, P., Hua, E., Ali, S. N. & Nisa, M. (2010). Acta Cryst. E66, o711.]). For standard bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data

  • C13H9NO2

  • Mr = 211.21

  • Monoclinic, P 21

  • a = 5.870 (1) Å

  • b = 3.8345 (7) Å

  • c = 21.733 (4) Å

  • [beta] = 91.059 (7)°

  • V = 489.09 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 113 K

  • 0.22 × 0.18 × 0.08 mm
Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.979, Tmax = 0.992

  • 4358 measured reflections

  • 1222 independent reflections

  • 1092 reflections with I > 2[sigma](I)

  • Rint = 0.032
Refinement

  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.085

  • S = 1.10

  • 1222 reflections

  • 147 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O2i 0.95 2.27 3.109 (2) 147
Symmetry code: (i) x-1, y-1, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: RZ2449 ).

Acknowledgements

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).

References

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.  [ChemPort]
Khan, S. T., Yu, P., Hua, E., Ali, S. N. & Nisa, M. (2010). Acta Cryst. E66, o711.  [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2010). E66, o1469  [ doi:10.1107/S1600536810017940 ]

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