2-Chloro-3-[(E)-(hydrazin-1-ylidene)methyl]-6-methoxyquinoline

In the title compound, C11H10ClN3O, the quinoline ring system is essentially planar, the r.m.s. deviation for the non-H atoms being 0.014 (2) Å with a maximum deviation from the mean plane of 0.0206 (14) Å for the C atom bonded to the –CH—N=NH2 group. In the crystal, molecules are linked via N—H⋯O and N—H⋯N hydrogen bonds, forming zigzag layers parallel to (010).

In the title compound, C 11 H 10 ClN 3 O, the quinoline ring system is essentially planar, the r.m.s. deviation for the non-H atoms being 0.014 (2) Å with a maximum deviation from the mean plane of 0.0206 (14) Å for the C atom bonded to the -CH-N NH 2 group. In the crystal, molecules are linked via N-HÁ Á ÁO and N-HÁ Á ÁN hydrogen bonds, forming zigzag layers parallel to (010).

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Acta Cryst. Pyrazole and its derivatives are gaining importance in medicinal and organic chemistry. They have displayed broad spectrum of pharmacological and biological activities such as anti-bacterial, anti-depressant, and anti-hyperglycemic (Mali et al., 2010). Pyrazolo [3,4-b]quinolines have displayed bioactivities such as antiviral, antimalarial, lowering of serum cholesterol (Paul et al., 2001), but no metal complexes of such drugs have been reported in the past which might possibly have better pharmaceutical effect. Therefore, studies of the metal complexes are important in the search for new drugs. In previous works, we were interested in the design and synthesis of new molecules that contain a quinolyl moiety (Belfaitah et al., 2006;Bouraiou et al., 2008Bouraiou et al., , 2011Ladraa et al., 2009 andBenzerka et al., 2011). In this paper, we report the structure determination of compound resulting from an unwanted reaction of the 6-methoxy-1H-pyrazolo[3,4b]quinoline with RuCl 3 in acidic conditions. Our attempt to synthesis the pyrazolo[3,4-b]quinoline/Ruthenium complex was failed and led to (E)-1-((2-chloro-6-methylquinolin-3-yl)methylene)hydrazine (I).
The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. In the asymetric unit of title molecule, (C 11 H 10 Cl N 3 O), the chloro-quinolyl unit is linked to methoxy and methylenehydrazine group. The quinoline ring system is essentially planar; the r.m.s. deviation for the non-H atoms is 0.014 (2) Å with a maximum deviation from the mean plane of 0.0206 (14) Å for the C atom bonded to the -CH-N═NH 2 group. The crystal packing can be described as layers in zigzag parallel to the (010) plane (Fig. 2). It is stabilized by N-H···O and N-H···N intermolecular hydrogen bonds (Fig. 2). These interaction bonds link the molecules within the layers and also link the layers together, reinforcing the cohesion of the structure. Hydrogen-bonding parameters are listed in table 1.

Refinement
All non-H atoms were refined with anisotropic atomic displacement parameters. All H atoms were localized on Fourier maps but introduced in calculated positions and treated as riding on their parent C or N atom. (with C-H = 0.95 and 0.98 Å, N-H = 0.88 Å and U iso (H) =1.5 or 1.2(carrier atom)).

Computing details
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 supplementary materials sup-2 Acta Cryst. (2012). E68, o1548 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).    Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.