Bioresmethrin: (5-benzyl­furan-3-yl)methyl 2,2-dimethyl-3-(2-methyl­prop-1-en-1-yl)cyclo­propane-1-carboxyl­ate

Kim, T.H.; Park, K.-M.; Jeon, Y.; Kim, J.

doi:10.1107/S1600536812040767

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3060

doi:10.1107/S1600536812040767

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Bioresmethrin: (5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

Tae Ho Kim,^a Ki-Min Park,^a ^* Youngeun Jeon ^a and Jineun Kim ^a ^*

^aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: kmpark@gnu.ac.kr, jekim@gnu.ac.kr

(Received 25 September 2012; accepted 27 September 2012; online 3 October 2012)

In the title compound, C₂₂H₂₆O₃, the dihedral angle between the cyclopropane ring and the plane of the vinyl group is 88.2 (2)°. The dihedral angle between the phenyl and furan rings is 86.09 (8)°. In the crystal, weak intermolecular C—H⋯π contacts together with very weak C—H⋯O hydrogen bonds stack the molecules along the a axis.

Related literature

For information on the insecticidal activity of the title compound, see: Hill et al. (1993 ). For a related structure, see: Yang et al. (2011 ).

Experimental

Crystal data

C₂₂H₂₆O₃
M_r = 338.43
Monoclinic, P 2₁
a = 7.8438 (14) Å
b = 11.555 (2) Å
c = 10.9649 (18) Å
β = 108.375 (3)°
V = 943.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.33 × 0.28 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.992
9877 measured reflections
2458 independent reflections
2156 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.096
S = 1.04
2458 reflections
230 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O3ⁱ	0.99	2.71	3.516 (3)	139
C11—H11⋯Cgⁱⁱ	0.95	2.63	3.559 (3)	167
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

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 global, I. DOI: 10.1107/S1600536812040767/sj5266sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812040767/sj5266Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812040767/sj5266Isup3.cml

checkCIF report

Comment top

Bioresmethrin (systematic name: 5-benzyl-3-furylmethyl- 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate), is a synthetic pyrethroid with high insecticidal activity aganist a wide range of insect pests (Hill et al., 1993). However its crystal structure has not yet been reported.

In the title compound (Scheme 1, Fig. 1), the dihedral angle between the cyclopropane ring plane and the vinyl group plane is 88.2 (2)°. The dihedral angle between the benzene and furan ring planes in the benzylfuranyl group is 86.09 (8)°. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Yang et al., 2011).

In the crystal structure (Fig. 2) weak intermolecular C—H···π interactions [C11···Cgⁱⁱ 3.559 (4) Å. Cg is the centroid of the C1—C6 ring. (Symmetry codes: (ii) x - 1, y, z) are found together with very weak C7–H7A···O3 hydrogen bonds, Table 1, stack the molecules along a. These intermolecular interactions may contribute to the stabilization of the packing.

Related literature top

For information on the insecticidal activity of the title compound, see: Hill et al. (1993). For a related structure, see: Yang et al. (2011).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.

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. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Crystal packing of the title compound with weak intermolecular C—H···π and C–H···O interactions shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. (Symmetry codes: (i) x + 1, y, z; (ii) x - 1, y, z; (iii) x - 2, y, z - 1; (iv) x - 1, y, z - 1; (v) x, y, z - 1.

(5-Benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate top

Crystal data top

C₂₂H₂₆O₃	F(000) = 364
M_r = 338.43	D_x = 1.192 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2685 reflections
a = 7.8438 (14) Å	θ = 2.6–26.3°
b = 11.555 (2) Å	µ = 0.08 mm⁻¹
c = 10.9649 (18) Å	T = 173 K
β = 108.375 (3)°	Plate, colourless
V = 943.2 (3) Å³	0.33 × 0.28 × 0.10 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	2458 independent reflections
Radiation source: fine-focus sealed tube	2156 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.975, T_max = 0.992	k = −15→15
9877 measured reflections	l = −13→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0305P)² + 0.1943P] where P = (F_o² + 2F_c²)/3
2458 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₂H₂₆O₃	V = 943.2 (3) Å³
M_r = 338.43	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.8438 (14) Å	µ = 0.08 mm⁻¹
b = 11.555 (2) Å	T = 173 K
c = 10.9649 (18) Å	0.33 × 0.28 × 0.10 mm
β = 108.375 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2458 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2156 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.992	R_int = 0.058
9877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
2458 reflections	Δρ_min = −0.17 e Å⁻³
230 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
O1	0.6817 (2)	−0.05992 (14)	1.05641 (15)	0.0323 (4)
O2	0.2777 (2)	0.11355 (14)	0.72431 (15)	0.0326 (4)
O3	0.0111 (2)	0.09696 (17)	0.75770 (16)	0.0393 (4)
C1	1.1967 (3)	−0.1520 (2)	1.1670 (3)	0.0378 (6)
H1	1.1775	−0.2312	1.1430	0.045*
C2	1.3371 (4)	−0.1216 (3)	1.2738 (3)	0.0491 (7)
H2	1.4143	−0.1797	1.3230	0.059*
C3	1.3657 (4)	−0.0084 (3)	1.3093 (3)	0.0531 (8)
H3	1.4630	0.0121	1.3830	0.064*
C4	1.2540 (4)	0.0764 (3)	1.2387 (3)	0.0499 (7)
H4	1.2731	0.1552	1.2642	0.060*
C5	1.1138 (3)	0.0463 (2)	1.1306 (3)	0.0363 (6)
H5	1.0381	0.1048	1.0810	0.044*
C6	1.0830 (3)	−0.0685 (2)	1.0940 (2)	0.0286 (5)
C7	0.9302 (3)	−0.1018 (2)	0.9759 (2)	0.0354 (5)
H7A	0.9666	−0.0862	0.8989	0.042*
H7B	0.9087	−0.1860	0.9787	0.042*
C8	0.7591 (3)	−0.03974 (19)	0.9623 (2)	0.0281 (5)
C9	0.6617 (3)	0.03791 (19)	0.8776 (2)	0.0280 (5)
H9	0.6877	0.0674	0.8045	0.034*
C10	0.5105 (3)	0.06772 (19)	0.9187 (2)	0.0274 (5)
C11	0.5305 (3)	0.0060 (2)	1.0258 (2)	0.0320 (5)
H11	0.4492	0.0080	1.0742	0.038*
C12	0.3638 (3)	0.1493 (2)	0.8562 (2)	0.0365 (6)
H12A	0.2748	0.1501	0.9032	0.044*
H12B	0.4128	0.2284	0.8581	0.044*
C13	0.1008 (3)	0.08949 (18)	0.6877 (2)	0.0259 (4)
C14	0.0392 (3)	0.05617 (17)	0.5514 (2)	0.0240 (4)
H14	0.1309	0.0644	0.5059	0.029*
C15	−0.1023 (3)	−0.03703 (18)	0.4976 (2)	0.0255 (4)
C16	−0.1542 (3)	0.08798 (18)	0.4709 (2)	0.0244 (4)
H16	−0.2295	0.1201	0.5214	0.029*
C17	−0.0750 (3)	−0.1108 (2)	0.3920 (2)	0.0316 (5)
H17A	−0.0064	−0.1802	0.4294	0.047*
H17B	−0.0087	−0.0666	0.3454	0.047*
H17C	−0.1920	−0.1337	0.3325	0.047*
C18	−0.1790 (3)	−0.1031 (2)	0.5866 (2)	0.0347 (5)
H18A	−0.2054	−0.0493	0.6474	0.052*
H18B	−0.0916	−0.1608	0.6340	0.052*
H18C	−0.2899	−0.1420	0.5363	0.052*
C19	−0.1846 (3)	0.14189 (19)	0.3437 (2)	0.0267 (4)
H19	−0.1285	0.1057	0.2885	0.032*
C20	−0.2821 (3)	0.23548 (19)	0.2982 (2)	0.0276 (5)
C21	−0.3813 (4)	0.3044 (2)	0.3695 (3)	0.0390 (6)
H21A	−0.3744	0.2650	0.4501	0.058*
H21B	−0.5075	0.3120	0.3167	0.058*
H21C	−0.3273	0.3815	0.3885	0.058*
C22	−0.2964 (4)	0.2819 (2)	0.1675 (2)	0.0387 (6)
H22A	−0.2335	0.2299	0.1254	0.058*
H22B	−0.2417	0.3590	0.1762	0.058*
H22C	−0.4232	0.2871	0.1156	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0341 (8)	0.0369 (9)	0.0243 (9)	0.0015 (7)	0.0069 (7)	0.0039 (7)
O2	0.0254 (8)	0.0411 (9)	0.0249 (9)	0.0036 (7)	−0.0015 (7)	−0.0062 (7)
O3	0.0382 (9)	0.0543 (11)	0.0258 (9)	−0.0059 (8)	0.0110 (8)	−0.0055 (8)
C1	0.0355 (13)	0.0412 (13)	0.0361 (15)	0.0070 (11)	0.0105 (12)	0.0076 (11)
C2	0.0380 (15)	0.073 (2)	0.0338 (16)	0.0106 (14)	0.0083 (12)	0.0147 (15)
C3	0.0280 (13)	0.094 (3)	0.0340 (17)	−0.0070 (15)	0.0048 (12)	−0.0053 (16)
C4	0.0377 (14)	0.0526 (17)	0.0597 (19)	−0.0127 (13)	0.0159 (14)	−0.0167 (15)
C5	0.0314 (12)	0.0364 (12)	0.0398 (15)	0.0012 (10)	0.0090 (11)	−0.0013 (11)
C6	0.0264 (10)	0.0353 (11)	0.0256 (12)	0.0022 (9)	0.0105 (9)	−0.0010 (10)
C7	0.0353 (12)	0.0376 (12)	0.0296 (13)	0.0068 (10)	0.0051 (10)	−0.0053 (10)
C8	0.0282 (11)	0.0307 (11)	0.0235 (12)	−0.0021 (9)	0.0054 (9)	−0.0049 (9)
C9	0.0298 (11)	0.0297 (11)	0.0223 (12)	−0.0029 (9)	0.0051 (9)	−0.0036 (9)
C10	0.0248 (10)	0.0294 (11)	0.0222 (12)	−0.0033 (8)	−0.0008 (9)	−0.0067 (9)
C11	0.0267 (11)	0.0408 (13)	0.0279 (13)	−0.0030 (9)	0.0079 (10)	−0.0036 (10)
C12	0.0348 (13)	0.0372 (13)	0.0297 (14)	0.0040 (10)	−0.0011 (11)	−0.0121 (11)
C13	0.0269 (10)	0.0230 (9)	0.0245 (11)	0.0024 (8)	0.0034 (9)	0.0028 (9)
C14	0.0231 (10)	0.0260 (10)	0.0226 (11)	0.0016 (8)	0.0066 (9)	0.0022 (8)
C15	0.0255 (10)	0.0257 (10)	0.0223 (11)	0.0012 (8)	0.0032 (9)	0.0024 (9)
C16	0.0239 (10)	0.0267 (10)	0.0216 (11)	0.0026 (8)	0.0056 (8)	0.0007 (9)
C17	0.0377 (13)	0.0253 (10)	0.0271 (13)	0.0009 (9)	0.0034 (10)	−0.0034 (9)
C18	0.0347 (12)	0.0370 (12)	0.0297 (13)	−0.0079 (10)	0.0064 (10)	0.0055 (10)
C19	0.0275 (10)	0.0291 (10)	0.0216 (11)	0.0023 (8)	0.0051 (9)	0.0002 (9)
C20	0.0271 (11)	0.0265 (10)	0.0240 (12)	−0.0010 (8)	0.0008 (9)	−0.0009 (9)
C21	0.0406 (13)	0.0316 (12)	0.0401 (15)	0.0083 (10)	0.0060 (12)	0.0001 (11)
C22	0.0491 (15)	0.0314 (12)	0.0288 (14)	0.0030 (11)	0.0026 (11)	0.0070 (10)

Geometric parameters (Å, º) top

O1—C11	1.360 (3)	C12—H12B	0.9900
O1—C8	1.372 (3)	C13—C14	1.470 (3)
O2—C13	1.346 (3)	C14—C15	1.525 (3)
O2—C12	1.450 (3)	C14—C16	1.540 (3)
O3—C13	1.197 (3)	C14—H14	1.0000
C1—C2	1.377 (4)	C15—C16	1.504 (3)
C1—C6	1.385 (3)	C15—C18	1.505 (3)
C1—H1	0.9500	C15—C17	1.508 (3)
C2—C3	1.363 (5)	C16—C19	1.476 (3)
C2—H2	0.9500	C16—H16	1.0000
C3—C4	1.379 (5)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.383 (4)	C17—H17C	0.9800
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.384 (3)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—C7	1.511 (3)	C19—C20	1.327 (3)
C7—C8	1.486 (3)	C19—H19	0.9500
C7—H7A	0.9900	C20—C21	1.495 (3)
C7—H7B	0.9900	C20—C22	1.501 (3)
C8—C9	1.344 (3)	C21—H21A	0.9800
C9—C10	1.437 (3)	C21—H21B	0.9800
C9—H9	0.9500	C21—H21C	0.9800
C10—C11	1.340 (3)	C22—H22A	0.9800
C10—C12	1.478 (3)	C22—H22B	0.9800
C11—H11	0.9500	C22—H22C	0.9800
C12—H12A	0.9900

C11—O1—C8	106.11 (18)	C13—C14—C16	117.97 (17)
C13—O2—C12	117.90 (18)	C15—C14—C16	58.78 (13)
C2—C1—C6	120.7 (3)	C13—C14—H14	115.1
C2—C1—H1	119.7	C15—C14—H14	115.1
C6—C1—H1	119.7	C16—C14—H14	115.1
C3—C2—C1	120.2 (3)	C16—C15—C18	118.33 (18)
C3—C2—H2	119.9	C16—C15—C17	119.24 (19)
C1—C2—H2	119.9	C18—C15—C17	113.2 (2)
C2—C3—C4	120.2 (3)	C16—C15—C14	61.09 (14)
C2—C3—H3	119.9	C18—C15—C14	119.90 (19)
C4—C3—H3	119.9	C17—C15—C14	115.70 (18)
C3—C4—C5	119.7 (3)	C19—C16—C15	122.87 (18)
C3—C4—H4	120.2	C19—C16—C14	118.61 (17)
C5—C4—H4	120.2	C15—C16—C14	60.13 (14)
C4—C5—C6	120.5 (3)	C19—C16—H16	114.8
C4—C5—H5	119.7	C15—C16—H16	114.8
C6—C5—H5	119.7	C14—C16—H16	114.8
C5—C6—C1	118.6 (2)	C15—C17—H17A	109.5
C5—C6—C7	120.7 (2)	C15—C17—H17B	109.5
C1—C6—C7	120.7 (2)	H17A—C17—H17B	109.5
C8—C7—C6	114.2 (2)	C15—C17—H17C	109.5
C8—C7—H7A	108.7	H17A—C17—H17C	109.5
C6—C7—H7A	108.7	H17B—C17—H17C	109.5
C8—C7—H7B	108.7	C15—C18—H18A	109.5
C6—C7—H7B	108.7	C15—C18—H18B	109.5
H7A—C7—H7B	107.6	H18A—C18—H18B	109.5
C9—C8—O1	110.07 (19)	C15—C18—H18C	109.5
C9—C8—C7	133.7 (2)	H18A—C18—H18C	109.5
O1—C8—C7	116.2 (2)	H18B—C18—H18C	109.5
C8—C9—C10	106.8 (2)	C20—C19—C16	127.0 (2)
C8—C9—H9	126.6	C20—C19—H19	116.5
C10—C9—H9	126.6	C16—C19—H19	116.5
C11—C10—C9	105.50 (19)	C19—C20—C21	124.8 (2)
C11—C10—C12	127.2 (2)	C19—C20—C22	120.7 (2)
C9—C10—C12	127.3 (2)	C21—C20—C22	114.5 (2)
C10—C11—O1	111.5 (2)	C20—C21—H21A	109.5
C10—C11—H11	124.2	C20—C21—H21B	109.5
O1—C11—H11	124.2	H21A—C21—H21B	109.5
O2—C12—C10	109.31 (18)	C20—C21—H21C	109.5
O2—C12—H12A	109.8	H21A—C21—H21C	109.5
C10—C12—H12A	109.8	H21B—C21—H21C	109.5
O2—C12—H12B	109.8	C20—C22—H22A	109.5
C10—C12—H12B	109.8	C20—C22—H22B	109.5
H12A—C12—H12B	108.3	H22A—C22—H22B	109.5
O3—C13—O2	123.6 (2)	C20—C22—H22C	109.5
O3—C13—C14	126.8 (2)	H22A—C22—H22C	109.5
O2—C13—C14	109.55 (17)	H22B—C22—H22C	109.5
C13—C14—C15	122.92 (18)

C6—C1—C2—C3	0.2 (4)	C12—O2—C13—O3	0.7 (3)
C1—C2—C3—C4	0.2 (4)	C12—O2—C13—C14	179.52 (18)
C2—C3—C4—C5	−0.8 (4)	O3—C13—C14—C15	−37.8 (3)
C3—C4—C5—C6	1.1 (4)	O2—C13—C14—C15	143.42 (19)
C4—C5—C6—C1	−0.8 (4)	O3—C13—C14—C16	31.4 (3)
C4—C5—C6—C7	−180.0 (2)	O2—C13—C14—C16	−147.39 (18)
C2—C1—C6—C5	0.2 (3)	C13—C14—C15—C16	105.1 (2)
C2—C1—C6—C7	179.3 (2)	C13—C14—C15—C18	−2.8 (3)
C5—C6—C7—C8	−43.0 (3)	C16—C14—C15—C18	−107.9 (2)
C1—C6—C7—C8	137.8 (2)	C13—C14—C15—C17	−144.2 (2)
C11—O1—C8—C9	1.3 (2)	C16—C14—C15—C17	110.7 (2)
C11—O1—C8—C7	179.2 (2)	C18—C15—C16—C19	−142.9 (2)
C6—C7—C8—C9	113.6 (3)	C17—C15—C16—C19	1.7 (3)
C6—C7—C8—O1	−63.7 (3)	C14—C15—C16—C19	106.6 (2)
O1—C8—C9—C10	−1.1 (2)	C18—C15—C16—C14	110.4 (2)
C7—C8—C9—C10	−178.5 (2)	C17—C15—C16—C14	−105.0 (2)
C8—C9—C10—C11	0.5 (2)	C13—C14—C16—C19	133.0 (2)
C8—C9—C10—C12	−179.5 (2)	C15—C14—C16—C19	−113.6 (2)
C9—C10—C11—O1	0.3 (2)	C13—C14—C16—C15	−113.4 (2)
C12—C10—C11—O1	−179.7 (2)	C15—C16—C19—C20	156.9 (2)
C8—O1—C11—C10	−1.0 (3)	C14—C16—C19—C20	−131.9 (2)
C13—O2—C12—C10	121.1 (2)	C16—C19—C20—C21	−0.2 (4)
C11—C10—C12—O2	−123.2 (2)	C16—C19—C20—C22	178.4 (2)
C9—C10—C12—O2	56.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3ⁱ	0.99	2.71	3.516 (3)	139
C11—H11···Cgⁱⁱ	0.95	2.63	3.559 (3)	167

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆O₃
M_r	338.43
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	7.8438 (14), 11.555 (2), 10.9649 (18)
β (°)	108.375 (3)
V (Å³)	943.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.33 × 0.28 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	9877, 2458, 2156
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.096, 1.04
No. of reflections	2458
No. of parameters	230
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3ⁱ	0.99	2.71	3.516 (3)	139
C11—H11···Cgⁱⁱ	0.95	2.63	3.559 (3)	167

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

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 (No. 2010–0009089).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.. Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hill, A. S., McAdam, D. P., Edward, S. L. & Skerritt, J. H. (1993). J. Agric. Food Chem. 41, 2011–2018. CrossRef CAS Web of Science 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
Yang, H., Kim, T. H., Park, K.-M. & Kim, J. (2011). Acta Cryst. E67, o1275. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3060

doi:10.1107/S1600536812040767

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bioresmethrin: (5-benzyl­furan-3-yl)methyl 2,2-di­methyl-3-(2-methyl­prop-1-en-1-yl)cyclo­propane-1-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

Bioresmethrin: (5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate