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Volume 68 
Part 12 
Page o3474  
December 2012  

Received 16 November 2012
Accepted 22 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.111
Data-to-parameter ratio = 17.3
Details
Open access

2-Amino-N,3-dimethylbenzamide

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
Correspondence e-mail: kbli@ippcaas.cn

In the title compound, C9H12N2O, the mean plane through the amide group and the benzene ring form a dihedral angle of 33.93 (7)°. An intramolecular N-H...O hydrogen bond is present. In the crystal, molecules are linked by N-H...N and N-H...O hydrogen bonds, forming double-stranded chains parallel to the b axis.

Related literature

For background to substituted anthranilamides, see: 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: Staiger & Wagner (1953[Staiger, R. P. & Wagner, E. C. (1953). J. Org. Chem. 18, 1427-1439.]); Coppola (1980[Coppola, G. M. (1980). Synthesis, 7, 505-536.]); Witt & Bergman (2000[Witt, A. & Bergman, J. (2000). Tetrahedron, 56, 7245-7253.]).

[Scheme 1]

Experimental

Crystal data
  • C9H12N2O

  • Mr = 164.21

  • Monoclinic, P 21

  • a = 9.833 (6) Å

  • b = 5.011 (3) Å

  • c = 9.841 (6) Å

  • [beta] = 118.27 (1)°

  • V = 427.1 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.36 × 0.13 × 0.10 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 = 0.970, Tmax = 0.992

  • 3828 measured reflections

  • 1939 independent reflections

  • 1884 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.111

  • S = 1.05

  • 1939 reflections

  • 112 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1 0.88 2.21 2.785 (2) 123
N1-H1B...N1i 0.88 2.44 3.240 (2) 151
N2-H2...O1ii 0.88 2.18 2.858 (2) 133
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+1]; (ii) x, y+1, 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: 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5025 ).


Acknowledgements

This work was supported by the Natural Science Foundation of China (No. 31101448) and the Special Fund for Agro-Scientific Research in the Public Interest (No. 201003025) of the Chinese government.

References

Coppola, G. M. (1980). Synthesis, 7, 505-536.  [CrossRef]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
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]
Norman, M. H., Rigdon, G. C., Hall, W. R. & Navas, F. III (1996). J. Med. Chem. 39, 1172-1188.  [CrossRef] [ChemPort] [PubMed] [ISI]
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] [details]
Staiger, R. P. & Wagner, E. C. (1953). J. Org. Chem. 18, 1427-1439.  [CrossRef] [ChemPort]
Witt, A. & Bergman, J. (2000). Tetrahedron, 56, 7245-7253.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3474  [ doi:10.1107/S1600536812048027 ]

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