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Volume 68 
Part 11 
Page o3189  
November 2012  

Received 28 September 2012
Accepted 10 October 2012
Online 20 October 2012

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.090
Data-to-parameter ratio = 27.2
Details
Open access

(2E)-1-[2,3-Dichloro-6-methyl-5-(trifluoromethyl)phenyl]-2-(1-phenylethylidene)hydrazine

Hoong-Kun Fun,a,b*+ Wan-Sin Loh,a++ Manjunath Bhat,c,d T. Arulmolic and G. K. Nagarajad

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia,cSequent Scientific Limited, Baikampady, Karnataka, India, and dDepartment of Chemistry, Mangalore University, Mangalagangothri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

The title compound, C16H13Cl2F3N2, exists in an E conformation with respect to the C=N bond [1.2952 (11) Å] and the C-N-N=C torsion angle is 175.65 (8)°. The dihedral angle between the benzene rings is 42.09 (4)°. An intramolecular C-H...F hydrogen bond generates an S(6) ring. In the crystal, the molecules are linked into [101] chains by C-H...F hydrogen bonds.

Related literature

For background to the properties and applications of hydrazones, see: Barbazan et al. (2008[Barbazan, P., Carballo, R., Covelo, B., Lodeiro, C., Lima, J. C. & Vazquez-Lopez, E. M. (2008). Eur. J. Inorg. Chem. pp. 2713-2716.]); Banerjee et al. (2009[Banerjee, S., Mondal, S., Chakraborty, W., Sen, S., Gachhui, R., Butcher, R. J., Slawin, A. M. Z., Mandal, C. & Mitra, S. (2009). Polyhedron, 28, 2785-2793.]); Ghavtadze et al. (2008[Ghavtadze, N., Frohlich, R. & Wurthwein, E. U. (2008). Eur. J. Org. Chem. pp. 3656-3667.]). For related structures, see: Fun et al. (2011a[Fun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Nagaraja, G. K. (2011a). Acta Cryst. E67, o1933.],b[Fun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Prasad, D. J. (2011b). Acta Cryst. E67, o1932.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C16H13Cl2F3N2

  • Mr = 361.18

  • Monoclinic, P 21 /c

  • a = 11.2600 (16) Å

  • b = 11.4025 (17) Å

  • c = 14.8398 (16) Å

  • [beta] = 123.773 (7)°

  • V = 1583.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.44 mm-1

  • T = 100 K

  • 0.32 × 0.26 × 0.22 mm
Data collection

  • Bruker SMART APEXII Duo CCD diffractometer

  • Absorption correction: multi-scan (SADABS); Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.872, Tmax = 0.911

  • 22269 measured reflections

  • 5714 independent reflections

  • 5043 reflections with I > 2[sigma](I)

  • Rint = 0.023
Refinement

  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.090

  • S = 1.02

  • 5714 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1A...F1i 0.95 2.39 3.1652 (14) 139
C15-H15A...F2 0.98 2.38 3.1018 (13) 130
Symmetry code: (i) x-1, y, z-1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6964 ).

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the position of Research Officer under the Research University Grant (1001/PFIZIK/811160).

References

Banerjee, S., Mondal, S., Chakraborty, W., Sen, S., Gachhui, R., Butcher, R. J., Slawin, A. M. Z., Mandal, C. & Mitra, S. (2009). Polyhedron, 28, 2785-2793.  [ISI] [CSD] [CrossRef] [ChemPort]
Barbazan, P., Carballo, R., Covelo, B., Lodeiro, C., Lima, J. C. & Vazquez-Lopez, E. M. (2008). Eur. J. Inorg. Chem. pp. 2713-2716.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Fun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Nagaraja, G. K. (2011a). Acta Cryst. E67, o1933.  [CrossRef] [details]
Fun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Prasad, D. J. (2011b). Acta Cryst. E67, o1932.  [CrossRef] [details]
Ghavtadze, N., Frohlich, R. & Wurthwein, E. U. (2008). Eur. J. Org. Chem. pp. 3656-3667.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2012). E68, o3189  [ doi:10.1107/S1600536812042419 ]

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