Benzoximate

Tae Ho Kim; Suk-Hee Moon; Jineun Kim; Ki-Min Park

doi:10.1107/S1600536812044248

. 2012 Oct 31;68(Pt 11):o3237. doi: 10.1107/S1600536812044248

Benzoximate

Tae Ho Kim ^a, Suk-Hee Moon ^b, Jineun Kim ^a,^*, Ki-Min Park ^a,^*

PMCID: PMC3515316 PMID: 23284536

Abstract

In the title compound [systematic name: (3-chloro-2,6-dimethoxyphenyl)(ethoxyimino)methyl benzoate], C₁₈H₁₈ClNO₅, the phenyl and chlorodimethoxyphenyl rings are linked by the ethoxyiminomethyl benzoate system such that they are almost perpendicular to each other with the dihedral angle between them being 85.72 (9)°. In the crystal, C—H⋯O and C—H⋯Cl hydrogen bonds between the phenyl and chlorodimethoxyphenyl rings generate R ₂ ²(8) rings which link the molecules into zigzag chains along the b axis. Additional C—H⋯O contacts, together with weak intermolecular C—H⋯π interactions, further link the molecules into a three-dimensional network.

Related literature

For information on the toxicity of the title compound, see: Kim et al. (2007 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₈H₁₈ClNO₅
M _r = 363.78
Monoclinic,
a = 9.4262 (10) Å
b = 12.9863 (14) Å
c = 15.4227 (16) Å
β = 102.843 (2)°
V = 1840.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 223 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.933, T _max = 0.977
9736 measured reflections
3606 independent reflections
2298 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.138
S = 1.10
3606 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Click here for additional data file.^{(24.7KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044248/sj5275sup1.cif

e-68-o3237-sup1.cif^{(24.7KB, cif)}

Click here for additional data file.^{(176.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044248/sj5275Isup2.hkl

e-68-o3237-Isup2.hkl^{(176.8KB, hkl)}

Click here for additional data file.^{(6.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812044248/sj5275Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C1–C6 and the C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O5ⁱ	0.94	2.57	3.409 (4)	148
C17—H17⋯O1ⁱⁱ	0.94	2.63	3.496 (4)	154
C18—H18⋯Cl1ⁱⁱ	0.94	2.89	3.716 (3)	147
C7—H7A⋯Cg1ⁱⁱⁱ	0.97	2.90	3.570 (4)	127
C10—H10A⋯Cg2^iv	0.98	3.01	3.740 (5)	132

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

Acknowledgments

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 Nos. 2012M2B2A4029305 and 2012-0007693).

supplementary crystallographic information

Comment

Benzoximate (IUPAC name: (3-chloro-2,6-dimethoxyphenyl)(ethoxyimino)methyl benzoate) is an acaricide widely used in agriculture targeting ticks and mites (Kim et al., 2007). However, until now its crystal structure has not been reported.

In the title compound (Fig. 1), the two aromatic rings are almost perpendicular to each other with the dihedral angle between them being 85.72 (9)°. Of the two methoxy methyl groups, one (C7) is almost perpendicular to the benzene ring plane [torsion angle C1–C6–O1–C7 = 84.0 (4) °] whereas the other (C8) is nearly parallel to it [torsion angle C3–C4–O2–C8 = 3.8 (5) °]. All the bond distances and bond angles within the molecule agree with values reported in the Cambridge Structural Database (Allen, 2002).

In the crystal, C17—H17···O1 and C18—H18···Cl1 hydrogen bonds generate R²₂(8) rings (Bernstein et al., 1995). Additional C3—H3···O5 hydrogen bonds and C–H···π contacts, Table 1, further link the molecules into a three dimensional network.

Experimental

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. X-ray quality single crystals were obtained by slow evaporation of a solution of the title compound in dichloromethane at room temperature.