[Journal logo]

Volume 69 
Part 8 
Page o1300  
August 2013  

Received 8 July 2013
Accepted 17 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.062
wR = 0.182
Data-to-parameter ratio = 16.2
Details
Open access

Amitraz

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea, and bTest and Analytical Laboratory, Korea Food and Drug Administration, 123-7 Yongdang-dong, Busan 608-829, Republic of Korea
Correspondence e-mail: jekim@gnu.ac.kr, thkim@gnu.ac.kr

In the asymmetric unit of the title compound {systematic name: N'-(2,4-dimethylphenyl)-N-[N-(2,4-dimethylphenyl)carboximidoyl]-N-methylmethanimidamide}, C19H23N3, which is a formamidine pesticide, there are two independent and conformationally similar molecules, with the dihedral angle between the mean planes of the 2,4-dimethylbenzene rings in each molecule being 41.63 (6) and 42.09 (5)°. The crystal structure is stabilized by a C-H...N hydrogen bond, as well as weak intermolecular C-H...[pi] and [pi]-[pi] interactions [ring centroid separation = 3.7409 (15) Å], giving one-dimensional chains extending down the b direction.

Related literature

For the toxicity and insecticidal properties of the title compound, see: Del Pino et al. (2013[Del Pino, J., Martinez, M. A., Castellano, V., Ramos, E., Martinez-Larranaga, M. R. & Anadon, A. (2013). Toxicology, 308, 88-95.]); Hollingworth (1976[Hollingworth, R. M. (1976). Environ. Health Perspect. 14, 57-69.]). For a related crystal structure, see: Peoples et al. (2012[Peoples, B. C., De la Vega, G., Valdebenito, C., Quijada, R., Ibañez, A., Valderrama, M. & Rojas, R. (2012). J. Organomet. Chem. 700, 147-153.]).

[Scheme 1]

Experimental

Crystal data
  • C19H23N3

  • Mr = 293.40

  • Monoclinic, P 21 /c

  • a = 11.9362 (11) Å

  • b = 7.5110 (7) Å

  • c = 37.514 (3) Å

  • [beta] = 91.650 (2)°

  • V = 3361.9 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 173 K

  • 0.40 × 0.40 × 0.40 mm

Data collection
  • Bruker APEXII CCD-detecto diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.973

  • 18091 measured reflections

  • 6593 independent reflections

  • 3615 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.182

  • S = 0.98

  • 6593 reflections

  • 407 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the C2-C8 and C31-C38 rings.

D-H...A D-H H...A D...A D-H...A
C29-H29C...N3i 0.98 2.49 3.334 (4) 144
C17-H17A...Cg4i 0.98 2.92 3.806 (3) 151
C24-H24A...Cg1ii 0.98 2.85 3.828 (3) 175
C33-H33B...Cg4iii 0.98 2.88 3.625 (3) 134
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2270 ).


Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (grant No. 2012R1A1B3003337).

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Del Pino, J., Martinez, M. A., Castellano, V., Ramos, E., Martinez-Larranaga, M. R. & Anadon, A. (2013). Toxicology, 308, 88-95.  [CrossRef] [ChemPort] [PubMed]
Hollingworth, R. M. (1976). Environ. Health Perspect. 14, 57-69.  [CrossRef] [ChemPort] [PubMed]
Peoples, B. C., De la Vega, G., Valdebenito, C., Quijada, R., Ibañez, A., Valderrama, M. & Rojas, R. (2012). J. Organomet. Chem. 700, 147-153.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1300  [ doi:10.1107/S1600536813019764 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.