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Volume 69 
Part 2 
Page o230  
February 2013  

Received 19 December 2012
Accepted 5 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.063
wR = 0.161
Data-to-parameter ratio = 15.6
Details
Open access

Methyl N-hydroxy-N-(2-methylphenyl)carbamate

aCatalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: chrc@zjut.edu.cn

There are three independent molecules in the asymmetric unit of the title compound, C9H11NO3, which are connected by O-H...O hydrogen bonds, forming an R33(15) ring. The dihedral angles between the planes of the benzene and amide groups are 75.16 (3), 71.47 (3) and 70.56 (3)°. The hydroxy O atom lies 0.912 (3), 1.172 (2) and 1.339 (2) Å from the mean plane of the corresponding benzene ring in the three molecules.

Related literature

The title compound is an intermediate in the synthesis of the strobilurin fungicide pyraclostrobin. For general background, see: Hou et al. (2002[Hou, C.-Q., Li, Z.-N. & Liu, C.-L. (2002). Pesticides, 41, 41-43.]); Yang et al. (2012[Yang, L.-J. & Bai, Y.-L. (2012). Mod. Agrochem. 11, 46-50.]); Tao et al. (2009[Tao, X.-J., Luo, L.-M., Huang, C.-Q. & Xiong, L.-L. (2009). Agrochem. Res. Appl. 41, 41-43.]). For related structures, see: Mercader et al. (2011[Mercader, J. V., Agullo, C., Abad-Somovilla, A. & Abad-Fuentes, A. (2011). Org. Biomol. Chem. 9, 1443-1453.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C9H11NO3

  • Mr = 181.19

  • Monoclinic, P 21 /n

  • a = 7.6418 (3) Å

  • b = 20.8825 (9) Å

  • c = 18.0412 (9) Å

  • [beta] = 94.485 (1)°

  • V = 2870.2 (2) Å3

  • Z = 12

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.54 × 0.37 × 0.18 mm

Data collection
  • Rigaku R-AXIS RAPID/ZJUG diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.946, Tmax = 0.983

  • 24402 measured reflections

  • 5643 independent reflections

  • 3163 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.161

  • S = 1.01

  • 5643 reflections

  • 362 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1A-H1A...O2B 0.82 1.94 2.719 (3) 157
O1B-H1B...O2C 0.82 1.94 2.716 (3) 157
O1C-H1C...O2A 0.82 1.99 2.757 (3) 156

Data collection: PROCESS-AUTO (Rigaku, 2006[Rigaku (2006). PROCESS_AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.]); 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.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2462 ).


Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (No. Y4110373). We are also grateful for the help of Professor Jian-Ming Gu of Zhejiang University.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Hou, C.-Q., Li, Z.-N. & Liu, C.-L. (2002). Pesticides, 41, 41-43.  [ChemPort]
Mercader, J. V., Agullo, C., Abad-Somovilla, A. & Abad-Fuentes, A. (2011). Org. Biomol. Chem. 9, 1443-1453.  [CrossRef] [ChemPort] [PubMed]
Rigaku (2006). PROCESS_AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tao, X.-J., Luo, L.-M., Huang, C.-Q. & Xiong, L.-L. (2009). Agrochem. Res. Appl. 41, 41-43.
Yang, L.-J. & Bai, Y.-L. (2012). Mod. Agrochem. 11, 46-50.  [ChemPort]


Acta Cryst (2013). E69, o230  [ doi:10.1107/S1600536813000421 ]

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