Benzoximate

Kim, T.H.; Moon, S.-H.; Kim, J.; Park, K.-M.

doi:10.1107/S1600536812044248

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3237

doi:10.1107/S1600536812044248

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Benzoximate

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

^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 ). 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, 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 ) 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[F² > 2σ(F²)] = 0.073
wR(F²) = 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

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
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 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812044248/sj5275sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812044248/sj5275Isup3.cml

checkCIF report

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.

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

Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.

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

C₁₈H₁₈ClNO₅	F(000) = 760
M_r = 363.78	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2737 reflections
a = 9.4262 (10) Å	θ = 2.2–25.6°
b = 12.9863 (14) Å	µ = 0.23 mm⁻¹
c = 15.4227 (16) Å	T = 223 K
β = 102.843 (2)°	Block, colourless
V = 1840.7 (3) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.933, T_max = 0.977	k = −8→16
9736 measured reflections	l = −18→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0351P)² + 1.3636P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₁₈ClNO₅	V = 1840.7 (3) Å³
M_r = 363.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4262 (10) Å	µ = 0.23 mm⁻¹
b = 12.9863 (14) Å	T = 223 K
c = 15.4227 (16) Å	0.30 × 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)
T_min = 0.933, T_max = 0.977	R_int = 0.049
9736 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.10	Δρ_max = 0.22 e Å⁻³
3606 reflections	Δρ_min = −0.30 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cl1	0.31473 (12)	0.56710 (7)	0.07179 (7)	0.0649 (3)
O1	0.1499 (2)	0.42350 (16)	0.16181 (13)	0.0405 (6)
O2	0.1097 (3)	0.15458 (19)	−0.04964 (16)	0.0583 (7)
O3	−0.1289 (3)	0.17796 (19)	0.17061 (16)	0.0578 (7)
O4	0.0986 (2)	0.12350 (16)	0.12436 (14)	0.0404 (6)
O5	0.2986 (3)	0.18389 (17)	0.21829 (15)	0.0484 (6)
N1	−0.0722 (3)	0.2521 (2)	0.12132 (17)	0.0415 (7)
C1	0.2563 (4)	0.4441 (3)	0.0356 (2)	0.0431 (9)
C2	0.2902 (4)	0.4053 (3)	−0.0402 (2)	0.0488 (9)
H2	0.3459	0.4449	−0.0714	0.059*
C3	0.2430 (4)	0.3084 (3)	−0.0708 (2)	0.0477 (9)
H3	0.2657	0.2823	−0.1229	0.057*
C4	0.1622 (3)	0.2502 (3)	−0.0243 (2)	0.0396 (8)
C5	0.1277 (3)	0.2883 (2)	0.0537 (2)	0.0328 (7)
C6	0.1751 (3)	0.3869 (2)	0.0833 (2)	0.0355 (8)
C7	0.0273 (4)	0.4934 (3)	0.1513 (2)	0.0539 (10)
H7A	0.0326	0.5436	0.1055	0.081*
H7B	0.0300	0.5287	0.2070	0.081*
H7C	−0.0627	0.4548	0.1342	0.081*
C8	0.1477 (6)	0.1095 (4)	−0.1262 (3)	0.0996 (19)
H8A	0.1149	0.1539	−0.1773	0.149*
H8B	0.1014	0.0427	−0.1378	0.149*
H8C	0.2525	0.1014	−0.1153	0.149*
C9	0.0461 (3)	0.2231 (2)	0.10433 (19)	0.0331 (7)
C10	−0.2591 (5)	0.2193 (3)	0.1924 (3)	0.0682 (12)
H10A	−0.2394	0.2897	0.2147	0.082*
H10B	−0.2832	0.1780	0.2404	0.082*
C11	−0.3862 (5)	0.2206 (4)	0.1162 (3)	0.0910 (16)
H11A	−0.3699	0.2706	0.0727	0.137*
H11B	−0.4727	0.2393	0.1368	0.137*
H11C	−0.3991	0.1529	0.0891	0.137*
C12	0.2377 (3)	0.1144 (2)	0.17402 (19)	0.0328 (7)
C13	0.2986 (3)	0.0111 (2)	0.16451 (19)	0.0311 (7)
C14	0.2277 (3)	−0.0602 (2)	0.1025 (2)	0.0390 (8)
H14	0.1367	−0.0443	0.0658	0.047*
C15	0.2915 (4)	−0.1537 (3)	0.0952 (2)	0.0466 (9)
H15	0.2432	−0.2023	0.0539	0.056*
C16	0.4257 (4)	−0.1772 (3)	0.1479 (2)	0.0479 (9)
H16	0.4684	−0.2415	0.1422	0.058*
C17	0.4976 (4)	−0.1070 (3)	0.2091 (2)	0.0487 (9)
H17	0.5895	−0.1230	0.2447	0.058*
C18	0.4341 (4)	−0.0130 (3)	0.2177 (2)	0.0412 (8)
H18	0.4824	0.0350	0.2597	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0716 (7)	0.0457 (5)	0.0686 (7)	−0.0158 (5)	−0.0033 (5)	0.0124 (5)
O1	0.0476 (14)	0.0375 (12)	0.0331 (12)	0.0087 (11)	0.0017 (10)	−0.0030 (10)
O2	0.0666 (19)	0.0633 (16)	0.0548 (16)	−0.0204 (14)	0.0342 (13)	−0.0286 (13)
O3	0.0556 (17)	0.0620 (16)	0.0683 (17)	0.0102 (13)	0.0405 (14)	0.0162 (14)
O4	0.0319 (13)	0.0349 (12)	0.0532 (14)	0.0003 (10)	0.0072 (11)	−0.0047 (11)
O5	0.0540 (16)	0.0413 (14)	0.0443 (14)	−0.0034 (12)	−0.0011 (12)	−0.0114 (12)
N1	0.0387 (17)	0.0502 (17)	0.0413 (16)	0.0052 (14)	0.0209 (13)	0.0051 (14)
C1	0.037 (2)	0.042 (2)	0.045 (2)	−0.0017 (16)	−0.0029 (17)	0.0071 (17)
C2	0.035 (2)	0.061 (2)	0.051 (2)	−0.0006 (18)	0.0107 (17)	0.017 (2)
C3	0.041 (2)	0.063 (2)	0.044 (2)	0.0027 (19)	0.0217 (17)	0.0002 (19)
C4	0.0301 (18)	0.049 (2)	0.0417 (19)	−0.0001 (16)	0.0116 (15)	−0.0066 (17)
C5	0.0265 (18)	0.0394 (18)	0.0324 (17)	0.0022 (14)	0.0061 (13)	−0.0020 (15)
C6	0.0343 (19)	0.0370 (18)	0.0309 (17)	0.0077 (15)	−0.0020 (14)	0.0005 (15)
C7	0.064 (3)	0.046 (2)	0.051 (2)	0.0208 (19)	0.0107 (19)	−0.0014 (18)
C8	0.130 (5)	0.099 (4)	0.093 (4)	−0.037 (3)	0.075 (3)	−0.063 (3)
C9	0.0339 (19)	0.0333 (17)	0.0318 (17)	0.0007 (15)	0.0065 (15)	−0.0051 (14)
C10	0.063 (3)	0.079 (3)	0.077 (3)	0.010 (2)	0.047 (2)	0.011 (2)
C11	0.054 (3)	0.140 (5)	0.088 (3)	0.007 (3)	0.036 (3)	0.001 (3)
C12	0.0356 (19)	0.0361 (18)	0.0292 (17)	−0.0038 (16)	0.0124 (15)	0.0001 (15)
C13	0.0314 (18)	0.0348 (17)	0.0282 (16)	−0.0014 (14)	0.0089 (14)	−0.0022 (14)
C14	0.0313 (19)	0.0422 (19)	0.0415 (18)	0.0051 (16)	0.0040 (15)	−0.0053 (16)
C15	0.041 (2)	0.044 (2)	0.053 (2)	0.0018 (17)	0.0070 (18)	−0.0115 (17)
C16	0.041 (2)	0.044 (2)	0.063 (2)	0.0039 (17)	0.0187 (19)	−0.0032 (18)
C17	0.0304 (19)	0.052 (2)	0.061 (2)	0.0066 (17)	0.0061 (17)	0.0089 (19)
C18	0.034 (2)	0.047 (2)	0.0396 (19)	−0.0028 (16)	0.0003 (15)	0.0001 (16)

Geometric parameters (Å, º) top

Cl1—C1	1.740 (3)	C7—H7C	0.9700
O1—C6	1.370 (4)	C8—H8A	0.9700
O1—C7	1.450 (4)	C8—H8B	0.9700
O2—C4	1.361 (4)	C8—H8C	0.9700
O2—C8	1.433 (4)	C10—C11	1.481 (6)
O3—N1	1.404 (3)	C10—H10A	0.9800
O3—C10	1.446 (4)	C10—H10B	0.9800
O4—C12	1.368 (4)	C11—H11A	0.9700
O4—C9	1.395 (4)	C11—H11B	0.9700
O5—C12	1.198 (3)	C11—H11C	0.9700
N1—C9	1.259 (4)	C12—C13	1.479 (4)
C1—C2	1.374 (5)	C13—C14	1.391 (4)
C1—C6	1.389 (5)	C13—C18	1.392 (4)
C2—C3	1.382 (5)	C14—C15	1.371 (4)
C2—H2	0.9400	C14—H14	0.9400
C3—C4	1.382 (5)	C15—C16	1.377 (5)
C3—H3	0.9400	C15—H15	0.9400
C4—C5	1.404 (4)	C16—C17	1.377 (5)
C5—C6	1.398 (4)	C16—H16	0.9400
C5—C9	1.478 (4)	C17—C18	1.379 (5)
C7—H7A	0.9700	C17—H17	0.9400
C7—H7B	0.9700	C18—H18	0.9400

C6—O1—C7	114.1 (2)	N1—C9—C5	121.8 (3)
C4—O2—C8	117.9 (3)	O4—C9—C5	116.6 (3)
N1—O3—C10	108.5 (3)	O3—C10—C11	113.4 (3)
C12—O4—C9	116.9 (2)	O3—C10—H10A	108.9
C9—N1—O3	111.7 (3)	C11—C10—H10A	108.9
C2—C1—C6	120.9 (3)	O3—C10—H10B	108.9
C2—C1—Cl1	119.5 (3)	C11—C10—H10B	108.9
C6—C1—Cl1	119.6 (3)	H10A—C10—H10B	107.7
C1—C2—C3	120.5 (3)	C10—C11—H11A	109.5
C1—C2—H2	119.8	C10—C11—H11B	109.5
C3—C2—H2	119.8	H11A—C11—H11B	109.5
C2—C3—C4	119.6 (3)	C10—C11—H11C	109.5
C2—C3—H3	120.2	H11A—C11—H11C	109.5
C4—C3—H3	120.2	H11B—C11—H11C	109.5
O2—C4—C3	123.9 (3)	O5—C12—O4	122.2 (3)
O2—C4—C5	115.4 (3)	O5—C12—C13	126.3 (3)
C3—C4—C5	120.7 (3)	O4—C12—C13	111.5 (3)
C6—C5—C4	119.0 (3)	C14—C13—C18	119.6 (3)
C6—C5—C9	121.2 (3)	C14—C13—C12	122.3 (3)
C4—C5—C9	119.8 (3)	C18—C13—C12	118.1 (3)
O1—C6—C1	120.4 (3)	C15—C14—C13	119.6 (3)
O1—C6—C5	120.0 (3)	C15—C14—H14	120.2
C1—C6—C5	119.4 (3)	C13—C14—H14	120.2
O1—C7—H7A	109.5	C14—C15—C16	120.6 (3)
O1—C7—H7B	109.5	C14—C15—H15	119.7
H7A—C7—H7B	109.5	C16—C15—H15	119.7
O1—C7—H7C	109.5	C15—C16—C17	120.4 (3)
H7A—C7—H7C	109.5	C15—C16—H16	119.8
H7B—C7—H7C	109.5	C17—C16—H16	119.8
O2—C8—H8A	109.5	C16—C17—C18	119.6 (3)
O2—C8—H8B	109.5	C16—C17—H17	120.2
H8A—C8—H8B	109.5	C18—C17—H17	120.2
O2—C8—H8C	109.5	C17—C18—C13	120.2 (3)
H8A—C8—H8C	109.5	C17—C18—H18	119.9
H8B—C8—H8C	109.5	C13—C18—H18	119.9
N1—C9—O4	121.2 (3)

C10—O3—N1—C9	176.3 (3)	O3—N1—C9—C5	−179.5 (3)
C6—C1—C2—C3	0.5 (5)	C12—O4—C9—N1	−126.9 (3)
Cl1—C1—C2—C3	−179.0 (3)	C12—O4—C9—C5	59.6 (3)
C1—C2—C3—C4	−0.5 (5)	C6—C5—C9—N1	58.3 (4)
C8—O2—C4—C3	3.8 (5)	C4—C5—C9—N1	−123.5 (3)
C8—O2—C4—C5	−176.9 (4)	C6—C5—C9—O4	−128.2 (3)
C2—C3—C4—O2	179.3 (3)	C4—C5—C9—O4	50.0 (4)
C2—C3—C4—C5	0.0 (5)	N1—O3—C10—C11	74.9 (4)
O2—C4—C5—C6	−178.7 (3)	C9—O4—C12—O5	19.6 (4)
C3—C4—C5—C6	0.6 (5)	C9—O4—C12—C13	−160.0 (2)
O2—C4—C5—C9	3.0 (4)	O5—C12—C13—C14	−171.1 (3)
C3—C4—C5—C9	−177.6 (3)	O4—C12—C13—C14	8.4 (4)
C7—O1—C6—C1	84.0 (4)	O5—C12—C13—C18	6.6 (5)
C7—O1—C6—C5	−100.4 (3)	O4—C12—C13—C18	−173.9 (3)
C2—C1—C6—O1	175.7 (3)	C18—C13—C14—C15	0.7 (5)
Cl1—C1—C6—O1	−4.7 (4)	C12—C13—C14—C15	178.3 (3)
C2—C1—C6—C5	0.1 (5)	C13—C14—C15—C16	−0.8 (5)
Cl1—C1—C6—C5	179.7 (2)	C14—C15—C16—C17	0.2 (5)
C4—C5—C6—O1	−176.3 (3)	C15—C16—C17—C18	0.4 (5)
C9—C5—C6—O1	1.9 (4)	C16—C17—C18—C13	−0.5 (5)
C4—C5—C6—C1	−0.7 (4)	C14—C13—C18—C17	0.0 (5)
C9—C5—C6—C1	177.5 (3)	C12—C13—C18—C17	−177.7 (3)
O3—N1—C9—O4	7.3 (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···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

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.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈ClNO₅
M_r	363.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	9.4262 (10), 12.9863 (14), 15.4227 (16)
β (°)	102.843 (2)
V (Å³)	1840.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.933, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	9736, 3606, 2298
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.138, 1.10
No. of reflections	3606
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C3—H3···O5ⁱ	0.94	2.57	3.409 (4)	148.3
C17—H17···O1ⁱⁱ	0.94	2.63	3.496 (4)	153.8
C18—H18···Cl1ⁱⁱ	0.94	2.89	3.716 (3)	146.8
C7—H7A···Cg1ⁱⁱⁱ	0.97	2.90	3.570 (4)	126.8
C10—H10A···Cg2^iv	0.98	3.01	3.740 (5)	132.3

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.

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

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Volume 68| Part 11| November 2012| Page o3237

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