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

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

doi:10.1107/S160053681203499X

. 2012 Aug 11;68(Pt 9):o2697. doi: 10.1107/S160053681203499X

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

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

PMCID: PMC3435717 PMID: 22969588

Abstract

In the title compound, C₁₇H₁₉NO₃, the dihedral angle between the benzene rings is 68.0 (1)°. The C—O—C—C torsion angle of the atoms joining these rings is 179.7 (2)°. The atoms of the methanol group were refined as disordered over two sets of sites with fixed occupancies of 0.86 and 0.14. The H atoms of the hydroxy group in the major component are disordered over a further two sets of sites with equal occupancies. This is a necessary arrangement to allow for hydrogen bonding without unrealistic H⋯H contacts. In the crystal, O—H⋯N and O—H⋯O hydrogen bonds connect molecules into chains along [001].

Related literature

The title compound was derived from kresoxim-methyl. For the biological activity of kresoxim-methyl, see: Anke et al. (1977 ▶); Clinton et al. (2011 ▶); Balba (2007 ▶); Sudisha et al. (2005 ▶). For related structures, see: Chopra et al. (2004 ▶); Kant et al. (2012a ▶,b ▶).

Experimental

Crystal data

C₁₇H₁₉NO₃
M _r = 285.33
Monoclinic,
a = 21.0394 (14) Å
b = 20.4128 (10) Å
c = 7.6711 (5) Å
β = 105.729 (6)°
V = 3171.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.790, T _max = 1.000
11340 measured reflections
2788 independent reflections
1497 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.212
S = 1.08
2788 reflections
204 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.22 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 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203499X/lh5508sup1.cif

e-68-o2697-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203499X/lh5508Isup2.hkl

e-68-o2697-Isup2.hkl^{(134.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681203499X/lh5508Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11A—H11Y⋯O11A ⁱ	0.84	1.77	2.614 (8)	178
O11A—H11Z⋯O11A ⁱⁱ	0.84	2.11	2.950 (14)	178
O11B—H11X⋯N3ⁱⁱⁱ	0.84	2.21	3.046 (18)	177

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

Acknowledgments

RK acknowledges the Department of Science & 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 a widely used agricultural fungicide of the strobilurin group (Anke et al., 1977; Clinton et al., 2011; Balba, 2007). It is a broad-spectrum systemic compound with novel mode of action (Sudisha et al., 2005). While exploring its fate in the environment, we have derived a new compound by the process of reduction. This may contribute to the understanding of the metabolic and environmental fate of this compound. The crystal structure of the title compound (I) is presented herein.

In (I)(Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related structures (Chopra et al., 2004; Kant et al., 2012a,b). The dihedral angle between the two benzene rings is 68.0 (1)°. The C—O—C—C torsion angle of the atoms joining these rings is 179.7 (2) °. The atoms of the methanol group were refined as disordered over two sets of sites with fixed occupancies of 0.86 and 0.14. The H atoms of the hydroxy group in the major component are disordered over a further two sets of sites with equal occupancies. This is a necessary arrangement to allow for hydrogen bonding without unrealistic H···H contacts. The O—H···O hydrogen bond motif of one the O—H disorder components is shown in Fig. 2. For the other disorder component in the O—H···O hydrogen bonds, the acceptors become donors and vice-versa. In the crystal, O—H···N and O—H···O hydrogen bonds connect molecules to form chains along [001].

Experimental

Finely powdered sodium borohydride (6 eq., 0.06 mol) was suspended in tetrahydrofuran in presence of kresoxim-methyl (3.13 g m, 0.01 mol) under reflux (343 K) with stirring for 1 h. Then methanol (8 ml) was slowly added drop wise. Stirring and refluxing were maintained until the reaction was completed as monitored by TLC. After the end of the reaction, the reaction mixture was cooled to room temperature and quenched with a saturated solution of ammonium chloride (15 ml) for further period of 1.5 h. The product was separated by extraction with ethyl acetate (2x25 ml). The organic extracts were combined and dried over sodium sulfate and concentrated under low pressure to yield the final product. The synthesized compound was dissolved in methanol and subjected to slow evaporation to produce colourless crystals.