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Volume 69 
Part 11 
Page o1642  
November 2013  

Received 28 September 2013
Accepted 10 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.065
wR = 0.139
Data-to-parameter ratio = 13.9
Details
Open access

2-Amino-6-chloro-N-methyl­benzamide

aState Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, People's Republic of China, and bPlant Protection Institute, Hebei Academy of Agricultural and Forestry Sciences, IPM Center of Hebei Province, Key Laboratory of Integrated Pest Management on Crops in Northern Region of North China, Ministry of Agriculture, Baoding 071000, People's Republic of China
Correspondence e-mail: xdmei@ippcaas.cn

In the title compound, C8H9ClN2O, the dihedral angle between the benzene ring and the methyl­amide substituent is 68.39 (11)°. In the crystal, mol­ecules are linked by N-H...O hydrogen bonds, forming layers parallel to the ab plane.

Related literature

For background information on substituted anthranilamides, see: Bharate et al. (2013[Bharate, S. B., Yadav, R. R., Khan, S. I., Tekwani, B. L., Jacob, M. R., Khan, I. A. & Vishwakarma, R. A. (2013). Med. Chem. Commun. 4, 1042-1048.]); Gnamm et al. (2012[Gnamm, C., Jeanguenat, A., Dutton, A. C., Grimm, C., Kloer, D. P. & Crossthwaite, A. J. (2012). Bioorg. Med. Chem. Lett. 22, 3800-3806.]); Lahm et al. (2005[Lahm, G. P., Selby, T. P., Freudenberger, J. H., Stevenson, T. M., Myers, B. J., Seburyamo, G., Smith, B. K., Flexner, L., Clark, C. E. & Cordova, D. (2005). Bioorg. Med. Chem. Lett. 15, 4898-4906.]); Norman et al. (1996[Norman, M. H., Rigdon, G. C., Hall, W. R. & Navas, F. III (1996). J. Med. Chem. 39, 1172-1188.]); Roe et al. (1999[Roe, M., Folkes, A., Ashworth, P., Brumwell, J., Chima, L., Hunjan, S., Pretswell, I., Dangerfield, W., Ryder, H. & Charlton, P. (1999). Bioorg. Med. Chem. Lett. 9, 595-600.]). For the synthesis, see: Witt & Bergman (2000[Witt, A. & Bergman, J. (2000). Tetrahedron, 56, 7245-7253.]); Coppola (1980[Coppola, G. M. (1980). Synthesis, 7, 505-536.]).

[Scheme 1]

Experimental

Crystal data
  • C8H9ClN2O

  • Mr = 184.62

  • Orthorhombic, P b c a

  • a = 9.2709 (19) Å

  • b = 11.812 (2) Å

  • c = 15.982 (3) Å

  • V = 1750.2 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.39 mm-1

  • T = 173 K

  • 0.43 × 0.25 × 0.18 mm

Data collection
  • Rigaku MM007-HF CCD (Saturn 724+) diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.609, Tmax = 1.000

  • 3865 measured reflections

  • 1528 independent reflections

  • 1351 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.139

  • S = 1.17

  • 1528 reflections

  • 110 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1B...O1i 0.86 2.11 2.970 (3) 175
N2-H2...O1ii 0.86 2.04 2.895 (4) 172
Symmetry codes: (i) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5085 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 31101448 and 31321004), the National Basic Research Program of China (2014CB932201 and 2012CB114104), the Public Service Sector R & D Project (200903033), the Open Fund of SKLBPI (SKL2012IP06), the National Key Technologies R & D Program of China (2011BAE06B03) and the Special Fund for Agro-Scientific Research in the Public Inter­est (No. 201003025) of the Chinese government.

References

Bharate, S. B., Yadav, R. R., Khan, S. I., Tekwani, B. L., Jacob, M. R., Khan, I. A. & Vishwakarma, R. A. (2013). Med. Chem. Commun. 4, 1042-1048.  [CrossRef] [ChemPort]
Coppola, G. M. (1980). Synthesis, 7, 505-536.  [CrossRef]
Gnamm, C., Jeanguenat, A., Dutton, A. C., Grimm, C., Kloer, D. P. & Crossthwaite, A. J. (2012). Bioorg. Med. Chem. Lett. 22, 3800-3806.  [CSD] [CrossRef] [ChemPort] [PubMed]
Lahm, G. P., Selby, T. P., Freudenberger, J. H., Stevenson, T. M., Myers, B. J., Seburyamo, G., Smith, B. K., Flexner, L., Clark, C. E. & Cordova, D. (2005). Bioorg. Med. Chem. Lett. 15, 4898-4906.  [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Norman, M. H., Rigdon, G. C., Hall, W. R. & Navas, F. III (1996). J. Med. Chem. 39, 1172-1188.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Roe, M., Folkes, A., Ashworth, P., Brumwell, J., Chima, L., Hunjan, S., Pretswell, I., Dangerfield, W., Ryder, H. & Charlton, P. (1999). Bioorg. Med. Chem. Lett. 9, 595-600.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Witt, A. & Bergman, J. (2000). Tetrahedron, 56, 7245-7253.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1642  [ doi:10.1107/S1600536813027827 ]

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