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Volume 69 
Part 11 
Page o1619  
November 2013  

Received 13 September 2013
Accepted 28 September 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.114
Data-to-parameter ratio = 13.7
Details
Open access

8-Meth­oxy-3-methyl-3,4-di­hydro-2H-1,3-benzoxazine

aSchool of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, People's Republic of China
Correspondence e-mail: yangxiangxianghaut@126.com

The title compound, C10H13NO2, crystallizes with two crystallographically independent mol­ecules of similar geometry in the asymmetric unit; the six-membered oxazine rings adopts a half-chair conformation. Neither hydrogen bonds nor [pi]-[pi] inter­actions are observed in the crystal structure.

Related literature

For the synthesis and applications of 1,3-benzoxazines, see: Holly & Cope (1944[Holly, F. W. & Cope, A. C. (1944). J. Am. Chem. Soc. 66, 1875-1879.]); Gu et al. (1998[Gu, Y., Xie, M. L., Liu, X. H., Li, Y., Zhang, J. H., Ling, H., Huang, Y. & Hu, Z. (1998). Chem. Ind. Eng. Prog. pp. 43-47.]); Zheng et al. (2011[Zheng, L., Zhang, C., Wang, Z., Zhao, P., Liu, X. & Gu, Y. (2011). J. Aero. Mater. 31, 62-66.]); Rimdusit & Ishida (2000[Rimdusit, S. & Ishida, H. (2000). Polymer, 41, 7941-7949.]); Stewart (2009[Stewart, R. (2009). Reinforced Plastics, 53, 28-33.]); Ning & Ishida (1994[Ning, X. & Ishida, H. (1994). J. Polym. Sci. Part A Polym. Chem. 32, 1121-1129.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13NO2

  • Mr = 179.21

  • Monoclinic, P 21 /c

  • a = 23.4234 (14) Å

  • b = 5.0054 (3) Å

  • c = 15.9408 (10) Å

  • [beta] = 97.210 (6)°

  • V = 1854.2 (2) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.73 mm-1

  • T = 291 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.783, Tmax = 1.000

  • 6857 measured reflections

  • 3281 independent reflections

  • 2471 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.114

  • S = 1.02

  • 3281 reflections

  • 240 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5083 ).


Acknowledgements

The authors thank Ms Y. Zhu for technical assistance. This research was supported by the Science and Technology Department of Henan Province of the People's Republic of China (grant No. 122102210111) and the Doctoral Scientific Fund Project of Henan University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gu, Y., Xie, M. L., Liu, X. H., Li, Y., Zhang, J. H., Ling, H., Huang, Y. & Hu, Z. (1998). Chem. Ind. Eng. Prog. pp. 43-47.
Holly, F. W. & Cope, A. C. (1944). J. Am. Chem. Soc. 66, 1875-1879.  [CrossRef] [ChemPort]
Ning, X. & Ishida, H. (1994). J. Polym. Sci. Part A Polym. Chem. 32, 1121-1129.  [CrossRef] [ChemPort]
Rimdusit, S. & Ishida, H. (2000). Polymer, 41, 7941-7949.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stewart, R. (2009). Reinforced Plastics, 53, 28-33.  [CrossRef]
Zheng, L., Zhang, C., Wang, Z., Zhao, P., Liu, X. & Gu, Y. (2011). J. Aero. Mater. 31, 62-66.  [ChemPort]


Acta Cryst (2013). E69, o1619  [ doi:10.1107/S1600536813026706 ]

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