2-Amino-N,3-dimethyl­benzamide

Mei, X.; Liang, Y.; Li, K.-B.

doi:10.1107/S1600536812048027

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 (C-C) = 0.003 Å
R = 0.042
wR = 0.111
Data-to-parameter ratio = 17.3
Details

2-Amino-N,3-dimethylbenzamide

Xiang-dong Mei,^a Yan-hui Liang ^a and Ke-Bin Li ^a ^*

^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-HO hydrogen bond is present. In the crystal, molecules are linked by N-HN and N-HO hydrogen bonds, forming double-stranded chains parallel to the b axis.

Related literature

For background to substituted anthranilamides, see: Gnamm et al. (2012); Lahm et al. (2005); Norman et al. (1996); Roe et al. (1999). For the synthesis, see: Staiger & Wagner (1953); Coppola (1980); Witt & Bergman (2000).

Experimental

Crystal data

C₉H₁₂N₂O
M_r = 164.21
Monoclinic, P 2₁
a = 9.833 (6) Å
b = 5.011 (3) Å
c = 9.841 (6) Å
= 118.27 (1)°
V = 427.1 (4) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.970, T_max = 0.992
3828 measured reflections
1939 independent reflections
1884 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.111
S = 1.05
1939 reflections
112 parameters
1 restraint
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1	0.88	2.21	2.785 (2)	123
N1-H1BN1ⁱ	0.88	2.44	3.240 (2)	151
N2-H2O1ⁱⁱ	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); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); 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.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Gnamm, C., Jeanguenat, A., Dutton, A. C., Grimm, C., Kloer, D. P. & Crossthwaite, A. J. (2012). Bioorg. Med. Chem. Lett. 22, 3800-3806.
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, M. H., Rigdon, G. C., Hall, W. R. & Navas, F. III (1996). J. Med. Chem. 39, 1172-1188.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Staiger, R. P. & Wagner, E. C. (1953). J. Org. Chem. 18, 1427-1439.
Witt, A. & Bergman, J. (2000). Tetrahedron, 56, 7245-7253.

organic compounds