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Volume 68 
Part 11 
Page o3237  
November 2012  

Received 22 October 2012
Accepted 25 October 2012
Online 31 October 2012

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Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.005 Å
R = 0.073
wR = 0.138
Data-to-parameter ratio = 15.7
Details
Open access

Benzoximate

Tae Ho Kim,a Suk-Hee Moon,b Jineun Kima* and Ki-Min Parka*

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea, and bDepartment of Food and Nutrition, Kyungnam College of Information and Technology, Busan 617-701, Republic of Korea
Correspondence e-mail: jekim@gnu.ac.kr, kmpark@gnu.ac.kr

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 R22(8) rings which link the molecules into zigzag chains along the b axis. Additional C-H...O contacts, together with weak intermolecular C-H...[pi] 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[Kim, Y.-J., Lee, S.-W., Cho, J.-R., Park, H.-M. & Ahn, Y.-J. (2007). J. Asia Pac. Entomol. 10, 165-170.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C18H18ClNO5

  • Mr = 363.78

  • Monoclinic, P 21 /c

  • a = 9.4262 (10) Å

  • b = 12.9863 (14) Å

  • c = 15.4227 (16) Å

  • [beta] = 102.843 (2)°

  • V = 1840.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.933, Tmax = 0.977

  • 9736 measured reflections

  • 3606 independent reflections

  • 2298 reflections with I > 2[sigma](I)

  • Rint = 0.049
Refinement

  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.138

  • S = 1.10

  • 3606 reflections

  • 229 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

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...Cg2iv 0.98 3.01 3.740 (5) 132
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x, -y+1, -z; (iv) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. 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 and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5275 ).

Acknowledgements

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).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kim, Y.-J., Lee, S.-W., Cho, J.-R., Park, H.-M. & Ahn, Y.-J. (2007). J. Asia Pac. Entomol. 10, 165-170.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2012). E68, o3237  [ doi:10.1107/S1600536812044248 ]

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