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ISSN: 2056-9890

Benzoximate

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

(Received 22 October 2012; accepted 25 October 2012; online 31 October 2012)

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⋯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[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

  • 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[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 > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.073

  • wR(F2) = 0.138

  • S = 1.10

  • 3606 reflections

  • 229 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −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 DA 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—H7ACg1iii 0.97 2.90 3.570 (4) 127
C10—H10ACg2iv 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.

Supporting information


Comment top

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.

Related literature top

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 top

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.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C–H) = 0.94 Å, Uiso = 1.2Ueq(C) for aromatic. d(C–H) = 0.98 Å, Uiso = 1.2Ueq(C) for methylene, and d(C–H) = 0.97 Å, Uiso = 1.5Ueq(C) for methyl protons.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound with intermolecular C–H···O and C–H···Cl hydrogen bonds and C–H···π interactions shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. Cg1 and Cg2 are the centroids of the C1–C6 and the C13–C18 rings, respectively. (Symmetry codes: (i) x, -y + 1/2, z - 1/2; (ii) -x + 1, y - 1/2, -z + 1/2; (iii) -x, -y + 1, -z; (iv) -x, y + 1/2, -z + 1/2.)
(3-Chloro-2,6-dimethoxyphenyl)(ethoxyimino)methyl benzoate top
Crystal data top
C18H18ClNO5F(000) = 760
Mr = 363.78Dx = 1.313 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2737 reflections
a = 9.4262 (10) Åθ = 2.2–25.6°
b = 12.9863 (14) ŵ = 0.23 mm1
c = 15.4227 (16) ÅT = 223 K
β = 102.843 (2)°Block, colourless
V = 1840.7 (3) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
3606 independent reflections
Radiation source: fine-focus sealed tube2298 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.933, Tmax = 0.977k = 816
9736 measured reflectionsl = 1819
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0351P)2 + 1.3636P]
where P = (Fo2 + 2Fc2)/3
3606 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C18H18ClNO5V = 1840.7 (3) Å3
Mr = 363.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.4262 (10) ŵ = 0.23 mm1
b = 12.9863 (14) ÅT = 223 K
c = 15.4227 (16) Å0.30 × 0.20 × 0.10 mm
β = 102.843 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
3606 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2298 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.977Rint = 0.049
9736 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0730 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.10Δρmax = 0.22 e Å3
3606 reflectionsΔρmin = 0.30 e Å3
229 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.31473 (12)0.56710 (7)0.07179 (7)0.0649 (3)
O10.1499 (2)0.42350 (16)0.16181 (13)0.0405 (6)
O20.1097 (3)0.15458 (19)0.04964 (16)0.0583 (7)
O30.1289 (3)0.17796 (19)0.17061 (16)0.0578 (7)
O40.0986 (2)0.12350 (16)0.12436 (14)0.0404 (6)
O50.2986 (3)0.18389 (17)0.21829 (15)0.0484 (6)
N10.0722 (3)0.2521 (2)0.12132 (17)0.0415 (7)
C10.2563 (4)0.4441 (3)0.0356 (2)0.0431 (9)
C20.2902 (4)0.4053 (3)0.0402 (2)0.0488 (9)
H20.34590.44490.07140.059*
C30.2430 (4)0.3084 (3)0.0708 (2)0.0477 (9)
H30.26570.28230.12290.057*
C40.1622 (3)0.2502 (3)0.0243 (2)0.0396 (8)
C50.1277 (3)0.2883 (2)0.0537 (2)0.0328 (7)
C60.1751 (3)0.3869 (2)0.0833 (2)0.0355 (8)
C70.0273 (4)0.4934 (3)0.1513 (2)0.0539 (10)
H7A0.03260.54360.10550.081*
H7B0.03000.52870.20700.081*
H7C0.06270.45480.13420.081*
C80.1477 (6)0.1095 (4)0.1262 (3)0.0996 (19)
H8A0.11490.15390.17730.149*
H8B0.10140.04270.13780.149*
H8C0.25250.10140.11530.149*
C90.0461 (3)0.2231 (2)0.10433 (19)0.0331 (7)
C100.2591 (5)0.2193 (3)0.1924 (3)0.0682 (12)
H10A0.23940.28970.21470.082*
H10B0.28320.17800.24040.082*
C110.3862 (5)0.2206 (4)0.1162 (3)0.0910 (16)
H11A0.36990.27060.07270.137*
H11B0.47270.23930.13680.137*
H11C0.39910.15290.08910.137*
C120.2377 (3)0.1144 (2)0.17402 (19)0.0328 (7)
C130.2986 (3)0.0111 (2)0.16451 (19)0.0311 (7)
C140.2277 (3)0.0602 (2)0.1025 (2)0.0390 (8)
H140.13670.04430.06580.047*
C150.2915 (4)0.1537 (3)0.0952 (2)0.0466 (9)
H150.24320.20230.05390.056*
C160.4257 (4)0.1772 (3)0.1479 (2)0.0479 (9)
H160.46840.24150.14220.058*
C170.4976 (4)0.1070 (3)0.2091 (2)0.0487 (9)
H170.58950.12300.24470.058*
C180.4341 (4)0.0130 (3)0.2177 (2)0.0412 (8)
H180.48240.03500.25970.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0716 (7)0.0457 (5)0.0686 (7)0.0158 (5)0.0033 (5)0.0124 (5)
O10.0476 (14)0.0375 (12)0.0331 (12)0.0087 (11)0.0017 (10)0.0030 (10)
O20.0666 (19)0.0633 (16)0.0548 (16)0.0204 (14)0.0342 (13)0.0286 (13)
O30.0556 (17)0.0620 (16)0.0683 (17)0.0102 (13)0.0405 (14)0.0162 (14)
O40.0319 (13)0.0349 (12)0.0532 (14)0.0003 (10)0.0072 (11)0.0047 (11)
O50.0540 (16)0.0413 (14)0.0443 (14)0.0034 (12)0.0011 (12)0.0114 (12)
N10.0387 (17)0.0502 (17)0.0413 (16)0.0052 (14)0.0209 (13)0.0051 (14)
C10.037 (2)0.042 (2)0.045 (2)0.0017 (16)0.0029 (17)0.0071 (17)
C20.035 (2)0.061 (2)0.051 (2)0.0006 (18)0.0107 (17)0.017 (2)
C30.041 (2)0.063 (2)0.044 (2)0.0027 (19)0.0217 (17)0.0002 (19)
C40.0301 (18)0.049 (2)0.0417 (19)0.0001 (16)0.0116 (15)0.0066 (17)
C50.0265 (18)0.0394 (18)0.0324 (17)0.0022 (14)0.0061 (13)0.0020 (15)
C60.0343 (19)0.0370 (18)0.0309 (17)0.0077 (15)0.0020 (14)0.0005 (15)
C70.064 (3)0.046 (2)0.051 (2)0.0208 (19)0.0107 (19)0.0014 (18)
C80.130 (5)0.099 (4)0.093 (4)0.037 (3)0.075 (3)0.063 (3)
C90.0339 (19)0.0333 (17)0.0318 (17)0.0007 (15)0.0065 (15)0.0051 (14)
C100.063 (3)0.079 (3)0.077 (3)0.010 (2)0.047 (2)0.011 (2)
C110.054 (3)0.140 (5)0.088 (3)0.007 (3)0.036 (3)0.001 (3)
C120.0356 (19)0.0361 (18)0.0292 (17)0.0038 (16)0.0124 (15)0.0001 (15)
C130.0314 (18)0.0348 (17)0.0282 (16)0.0014 (14)0.0089 (14)0.0022 (14)
C140.0313 (19)0.0422 (19)0.0415 (18)0.0051 (16)0.0040 (15)0.0053 (16)
C150.041 (2)0.044 (2)0.053 (2)0.0018 (17)0.0070 (18)0.0115 (17)
C160.041 (2)0.044 (2)0.063 (2)0.0039 (17)0.0187 (19)0.0032 (18)
C170.0304 (19)0.052 (2)0.061 (2)0.0066 (17)0.0061 (17)0.0089 (19)
C180.034 (2)0.047 (2)0.0396 (19)0.0028 (16)0.0003 (15)0.0001 (16)
Geometric parameters (Å, º) top
Cl1—C11.740 (3)C7—H7C0.9700
O1—C61.370 (4)C8—H8A0.9700
O1—C71.450 (4)C8—H8B0.9700
O2—C41.361 (4)C8—H8C0.9700
O2—C81.433 (4)C10—C111.481 (6)
O3—N11.404 (3)C10—H10A0.9800
O3—C101.446 (4)C10—H10B0.9800
O4—C121.368 (4)C11—H11A0.9700
O4—C91.395 (4)C11—H11B0.9700
O5—C121.198 (3)C11—H11C0.9700
N1—C91.259 (4)C12—C131.479 (4)
C1—C21.374 (5)C13—C141.391 (4)
C1—C61.389 (5)C13—C181.392 (4)
C2—C31.382 (5)C14—C151.371 (4)
C2—H20.9400C14—H140.9400
C3—C41.382 (5)C15—C161.377 (5)
C3—H30.9400C15—H150.9400
C4—C51.404 (4)C16—C171.377 (5)
C5—C61.398 (4)C16—H160.9400
C5—C91.478 (4)C17—C181.379 (5)
C7—H7A0.9700C17—H170.9400
C7—H7B0.9700C18—H180.9400
C6—O1—C7114.1 (2)N1—C9—C5121.8 (3)
C4—O2—C8117.9 (3)O4—C9—C5116.6 (3)
N1—O3—C10108.5 (3)O3—C10—C11113.4 (3)
C12—O4—C9116.9 (2)O3—C10—H10A108.9
C9—N1—O3111.7 (3)C11—C10—H10A108.9
C2—C1—C6120.9 (3)O3—C10—H10B108.9
C2—C1—Cl1119.5 (3)C11—C10—H10B108.9
C6—C1—Cl1119.6 (3)H10A—C10—H10B107.7
C1—C2—C3120.5 (3)C10—C11—H11A109.5
C1—C2—H2119.8C10—C11—H11B109.5
C3—C2—H2119.8H11A—C11—H11B109.5
C2—C3—C4119.6 (3)C10—C11—H11C109.5
C2—C3—H3120.2H11A—C11—H11C109.5
C4—C3—H3120.2H11B—C11—H11C109.5
O2—C4—C3123.9 (3)O5—C12—O4122.2 (3)
O2—C4—C5115.4 (3)O5—C12—C13126.3 (3)
C3—C4—C5120.7 (3)O4—C12—C13111.5 (3)
C6—C5—C4119.0 (3)C14—C13—C18119.6 (3)
C6—C5—C9121.2 (3)C14—C13—C12122.3 (3)
C4—C5—C9119.8 (3)C18—C13—C12118.1 (3)
O1—C6—C1120.4 (3)C15—C14—C13119.6 (3)
O1—C6—C5120.0 (3)C15—C14—H14120.2
C1—C6—C5119.4 (3)C13—C14—H14120.2
O1—C7—H7A109.5C14—C15—C16120.6 (3)
O1—C7—H7B109.5C14—C15—H15119.7
H7A—C7—H7B109.5C16—C15—H15119.7
O1—C7—H7C109.5C15—C16—C17120.4 (3)
H7A—C7—H7C109.5C15—C16—H16119.8
H7B—C7—H7C109.5C17—C16—H16119.8
O2—C8—H8A109.5C16—C17—C18119.6 (3)
O2—C8—H8B109.5C16—C17—H17120.2
H8A—C8—H8B109.5C18—C17—H17120.2
O2—C8—H8C109.5C17—C18—C13120.2 (3)
H8A—C8—H8C109.5C17—C18—H18119.9
H8B—C8—H8C109.5C13—C18—H18119.9
N1—C9—O4121.2 (3)
C10—O3—N1—C9176.3 (3)O3—N1—C9—C5179.5 (3)
C6—C1—C2—C30.5 (5)C12—O4—C9—N1126.9 (3)
Cl1—C1—C2—C3179.0 (3)C12—O4—C9—C559.6 (3)
C1—C2—C3—C40.5 (5)C6—C5—C9—N158.3 (4)
C8—O2—C4—C33.8 (5)C4—C5—C9—N1123.5 (3)
C8—O2—C4—C5176.9 (4)C6—C5—C9—O4128.2 (3)
C2—C3—C4—O2179.3 (3)C4—C5—C9—O450.0 (4)
C2—C3—C4—C50.0 (5)N1—O3—C10—C1174.9 (4)
O2—C4—C5—C6178.7 (3)C9—O4—C12—O519.6 (4)
C3—C4—C5—C60.6 (5)C9—O4—C12—C13160.0 (2)
O2—C4—C5—C93.0 (4)O5—C12—C13—C14171.1 (3)
C3—C4—C5—C9177.6 (3)O4—C12—C13—C148.4 (4)
C7—O1—C6—C184.0 (4)O5—C12—C13—C186.6 (5)
C7—O1—C6—C5100.4 (3)O4—C12—C13—C18173.9 (3)
C2—C1—C6—O1175.7 (3)C18—C13—C14—C150.7 (5)
Cl1—C1—C6—O14.7 (4)C12—C13—C14—C15178.3 (3)
C2—C1—C6—C50.1 (5)C13—C14—C15—C160.8 (5)
Cl1—C1—C6—C5179.7 (2)C14—C15—C16—C170.2 (5)
C4—C5—C6—O1176.3 (3)C15—C16—C17—C180.4 (5)
C9—C5—C6—O11.9 (4)C16—C17—C18—C130.5 (5)
C4—C5—C6—C10.7 (4)C14—C13—C18—C170.0 (5)
C9—C5—C6—C1177.5 (3)C12—C13—C18—C17177.7 (3)
O3—N1—C9—O47.3 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and the C13–C18 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3···O5i0.942.573.409 (4)148
C17—H17···O1ii0.942.633.496 (4)154
C18—H18···Cl1ii0.942.893.716 (3)147
C7—H7A···Cg1iii0.972.903.570 (4)127
C10—H10A···Cg2iv0.983.013.740 (5)132
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y1/2, z+1/2; (iii) x, y+1, z; (iv) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC18H18ClNO5
Mr363.78
Crystal system, space groupMonoclinic, P21/c
Temperature (K)223
a, b, c (Å)9.4262 (10), 12.9863 (14), 15.4227 (16)
β (°) 102.843 (2)
V3)1840.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.933, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
9736, 3606, 2298
Rint0.049
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.138, 1.10
No. of reflections3606
No. of parameters229
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.30

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and the C13–C18 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3···O5i0.942.573.409 (4)148.3
C17—H17···O1ii0.942.633.496 (4)153.8
C18—H18···Cl1ii0.942.893.716 (3)146.8
C7—H7A···Cg1iii0.972.903.570 (4)126.8
C10—H10A···Cg2iv0.983.013.740 (5)132.3
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y1/2, z+1/2; (iii) x, y+1, z; (iv) x, y+1/2, z+1/2.
 

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

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationKim, Y.-J., Lee, S.-W., Cho, J.-R., Park, H.-M. & Ahn, Y.-J. (2007). J. Asia Pac. Entomol. 10, 165–170.  CrossRef CAS
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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