2-(Meth­oxy­imino)-2-{2-[(2-methyl­phenoxy)meth­yl]phen­yl}acetohydrazide

Rajni Kant; Vivek K Gupta; Kamini Kapoor; Chetan S Shripanavar; Kaushik Banerjee

doi:10.1107/S160053681203070X

. 2012 Jul 10;68(Pt 8):o2426. doi: 10.1107/S160053681203070X

2-(Methoxyimino)-2-{2-[(2-methylphenoxy)methyl]phenyl}acetohydrazide

Rajni Kant ^a,^*, Vivek K Gupta ^a, Kamini Kapoor ^a, Chetan S Shripanavar ^b, Kaushik Banerjee ^c

PMCID: PMC3414344 PMID: 22904877

Abstract

In the title molecule, C₁₇H₁₉N₃O₃, the dihedral angle between the two benzene rings is 57.17 (5)°. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds connect molecules to form chains along [001]. In addition, a weak C—H⋯π interaction is observed.

Related literature

For the biological activities of kresoxim-methyl {methyl 2(E)-methoxyimino-2-[2-(2-tolyloxymethyl)phenyl] acetate}, which is a starting material in the synthesis of the title compound, see: Anke et al. (1977 ▶); Balba (2007 ▶); Ichinari et al. (1999 ▶); Grossmann & Retzlaff (1997 ▶); Ypema (1998 ▶). For the crystal structure of kresoxim-methyl, see: Chopra et al. (2004 ▶).

Experimental

Crystal data

C₁₇H₁₉N₃O₃
M _r = 313.35
Monoclinic,
a = 21.4015 (6) Å
b = 20.7277 (4) Å
c = 7.6975 (2) Å
β = 109.103 (3)°
V = 3226.60 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.906, T _max = 1.000
55120 measured reflections
3174 independent reflections
2532 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.105
S = 1.02
3174 reflections
222 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203070X/lh5499sup1.cif

e-68-o2426-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203070X/lh5499Isup2.hkl

e-68-o2426-Isup2.hkl^{(152.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681203070X/lh5499Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg refers to the centroid of the C8–C13 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H72⋯O1ⁱ	0.86 (2)	2.40 (2)	3.220 (2)	158 (2)
N6—H61⋯N7ⁱⁱ	0.87 (2)	2.34 (1)	3.191 (2)	166 (1)
C5—H5B⋯Cg ⁱⁱⁱ	0.96	2.69	3.461 (2)	138

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

RK acknowledges the Department of Science and Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.

supplementary crystallographic information

Comment

Kresoxim-methyl is an active agrochemical (Chopra et al., 2004), strobilurin fungicide (Anke et al., 1977), with broad spectrum biological activity (Ypema, 1998; Ichinari et al., 1999; Grossmann & Retzlaff 1997). This type of compound is easily metabolized in nature as well as in living systems, and that is the reason studies on their fate in soil, plants and animal systems (Balba, 2007) are very important. Herein, we present the crystal structure of the title compound (I) which was synthesized from kresoxim-methyl.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related structure (Chopra et al., 2004). The dihedral angles formed by the two benzene rings (C8-C13/C16-C21) is 57.17 (5)°. In the crystal, molecules are connected by N—H···O and N—H···N hydrogen bonds into chains along [001] (Fig. 2). In addition a weak C—H···π interaction is observed.

Experimental

Kresoxim-methyl (0.313 g, 0.001 mol) was dissolved in 5 ml methanol and to it hydrazine hydrate (0.1 g, 0.002 mol) solution was added and refluxed at 343K for 1 h. The reaction mixture was then cooled and solvent was removed under reduced presser to give a solid product. The compound was dissolved in methanol, and by the process of slow evaporation this crystalline compound was separated out, m.p. 397K.