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

Zhang, B.; Wang, Y.; Dong, K.; Xu, D.

doi:10.1107/S1600536813000421

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 (C-C) = 0.006 Å
R = 0.063
wR = 0.161
Data-to-parameter ratio = 15.6
Details

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

Binbin Zhang,^a Yifeng Wang,^a Kun Dong ^a and Danqian Xu ^a ^*

^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-HO 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); Yang et al. (2012); Tao et al. (2009). For related structures, see: Mercader et al. (2011). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₉H₁₁NO₃
M_r = 181.19
Monoclinic, P 2₁ /n
a = 7.6418 (3) Å
b = 20.8825 (9) Å
c = 18.0412 (9) Å
= 94.485 (1)°
V = 2870.2 (2) Å³
Z = 12
Mo K radiation
= 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) T_min = 0.946, T_max = 0.983
24402 measured reflections
5643 independent reflections
3163 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.161
S = 1.01
5643 reflections
362 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1A-H1AO2B	0.82	1.94	2.719 (3)	157
O1B-H1BO2C	0.82	1.94	2.716 (3)	157
O1C-H1CO2A	0.82	1.99	2.757 (3)	156

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Hou, C.-Q., Li, Z.-N. & Liu, C.-L. (2002). Pesticides, 41, 41-43.
Mercader, J. V., Agullo, C., Abad-Somovilla, A. & Abad-Fuentes, A. (2011). Org. Biomol. Chem. 9, 1443-1453.
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.
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.

organic compounds