Literature DB >> 23284395

Bioresmethrin: (5-benzyl-furan-3-yl)methyl 2,2-dimethyl-3-(2-methyl-prop-1-en-1-yl)cyclo-propane-1-carboxyl-ate.

Tae Ho Kim1, Ki-Min Park, Youngeun Jeon, Jineun Kim.   

Abstract

In the title compound, C(22)H(26)O(3), the dihedral angle between the cyclo-propane 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 inter-molecular C-H⋯π contacts together with very weak C-H⋯O hydrogen bonds stack the mol-ecules along the a axis.

Entities:  

Year:  2012        PMID： 23284395      PMCID： PMC3515168          DOI： 10.1107/S1600536812040767

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 338.43 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.096 S = 1.04 2458 reflections 230 parameters 1 restraint H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.17 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. Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040767/sj5266sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040767/sj5266Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812040767/sj5266Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H26O3F(000) = 364
Mr = 338.43Dx = 1.192 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2685 reflections
a = 7.8438 (14) Åθ = 2.6–26.3°
b = 11.555 (2) ŵ = 0.08 mm−1
c = 10.9649 (18) ÅT = 173 K
β = 108.375 (3)°Plate, colourless
V = 943.2 (3) Å30.33 × 0.28 × 0.10 mm
Z = 2
Bruker APEXII CCD diffractometer2458 independent reflections
Radiation source: fine-focus sealed tube2156 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.975, Tmax = 0.992k = −15→15
9877 measured reflectionsl = −13→14
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0305P)2 + 0.1943P] where P = (Fo2 + 2Fc2)/3
2458 reflections(Δ/σ)max = 0.001
230 parametersΔρmax = 0.20 e Å−3
1 restraintΔρmin = −0.17 e Å−3
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.
xyzUiso*/Ueq
O10.6817 (2)−0.05992 (14)1.05641 (15)0.0323 (4)
O20.2777 (2)0.11355 (14)0.72431 (15)0.0326 (4)
O30.0111 (2)0.09696 (17)0.75770 (16)0.0393 (4)
C11.1967 (3)−0.1520 (2)1.1670 (3)0.0378 (6)
H11.1775−0.23121.14300.045*
C21.3371 (4)−0.1216 (3)1.2738 (3)0.0491 (7)
H21.4143−0.17971.32300.059*
C31.3657 (4)−0.0084 (3)1.3093 (3)0.0531 (8)
H31.46300.01211.38300.064*
C41.2540 (4)0.0764 (3)1.2387 (3)0.0499 (7)
H41.27310.15521.26420.060*
C51.1138 (3)0.0463 (2)1.1306 (3)0.0363 (6)
H51.03810.10481.08100.044*
C61.0830 (3)−0.0685 (2)1.0940 (2)0.0286 (5)
C70.9302 (3)−0.1018 (2)0.9759 (2)0.0354 (5)
H7A0.9666−0.08620.89890.042*
H7B0.9087−0.18600.97870.042*
C80.7591 (3)−0.03974 (19)0.9623 (2)0.0281 (5)
C90.6617 (3)0.03791 (19)0.8776 (2)0.0280 (5)
H90.68770.06740.80450.034*
C100.5105 (3)0.06772 (19)0.9187 (2)0.0274 (5)
C110.5305 (3)0.0060 (2)1.0258 (2)0.0320 (5)
H110.44920.00801.07420.038*
C120.3638 (3)0.1493 (2)0.8562 (2)0.0365 (6)
H12A0.27480.15010.90320.044*
H12B0.41280.22840.85810.044*
C130.1008 (3)0.08949 (18)0.6877 (2)0.0259 (4)
C140.0392 (3)0.05617 (17)0.5514 (2)0.0240 (4)
H140.13090.06440.50590.029*
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)
H16−0.22950.12010.52140.029*
C17−0.0750 (3)−0.1108 (2)0.3920 (2)0.0316 (5)
H17A−0.0064−0.18020.42940.047*
H17B−0.0087−0.06660.34540.047*
H17C−0.1920−0.13370.33250.047*
C18−0.1790 (3)−0.1031 (2)0.5866 (2)0.0347 (5)
H18A−0.2054−0.04930.64740.052*
H18B−0.0916−0.16080.63400.052*
H18C−0.2899−0.14200.53630.052*
C19−0.1846 (3)0.14189 (19)0.3437 (2)0.0267 (4)
H19−0.12850.10570.28850.032*
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−0.37440.26500.45010.058*
H21B−0.50750.31200.31670.058*
H21C−0.32730.38150.38850.058*
C22−0.2964 (4)0.2819 (2)0.1675 (2)0.0387 (6)
H22A−0.23350.22990.12540.058*
H22B−0.24170.35900.17620.058*
H22C−0.42320.28710.11560.058*
U11U22U33U12U13U23
O10.0341 (8)0.0369 (9)0.0243 (9)0.0015 (7)0.0069 (7)0.0039 (7)
O20.0254 (8)0.0411 (9)0.0249 (9)0.0036 (7)−0.0015 (7)−0.0062 (7)
O30.0382 (9)0.0543 (11)0.0258 (9)−0.0059 (8)0.0110 (8)−0.0055 (8)
C10.0355 (13)0.0412 (13)0.0361 (15)0.0070 (11)0.0105 (12)0.0076 (11)
C20.0380 (15)0.073 (2)0.0338 (16)0.0106 (14)0.0083 (12)0.0147 (15)
C30.0280 (13)0.094 (3)0.0340 (17)−0.0070 (15)0.0048 (12)−0.0053 (16)
C40.0377 (14)0.0526 (17)0.0597 (19)−0.0127 (13)0.0159 (14)−0.0167 (15)
C50.0314 (12)0.0364 (12)0.0398 (15)0.0012 (10)0.0090 (11)−0.0013 (11)
C60.0264 (10)0.0353 (11)0.0256 (12)0.0022 (9)0.0105 (9)−0.0010 (10)
C70.0353 (12)0.0376 (12)0.0296 (13)0.0068 (10)0.0051 (10)−0.0053 (10)
C80.0282 (11)0.0307 (11)0.0235 (12)−0.0021 (9)0.0054 (9)−0.0049 (9)
C90.0298 (11)0.0297 (11)0.0223 (12)−0.0029 (9)0.0051 (9)−0.0036 (9)
C100.0248 (10)0.0294 (11)0.0222 (12)−0.0033 (8)−0.0008 (9)−0.0067 (9)
C110.0267 (11)0.0408 (13)0.0279 (13)−0.0030 (9)0.0079 (10)−0.0036 (10)
C120.0348 (13)0.0372 (13)0.0297 (14)0.0040 (10)−0.0011 (11)−0.0121 (11)
C130.0269 (10)0.0230 (9)0.0245 (11)0.0024 (8)0.0034 (9)0.0028 (9)
C140.0231 (10)0.0260 (10)0.0226 (11)0.0016 (8)0.0066 (9)0.0022 (8)
C150.0255 (10)0.0257 (10)0.0223 (11)0.0012 (8)0.0032 (9)0.0024 (9)
C160.0239 (10)0.0267 (10)0.0216 (11)0.0026 (8)0.0056 (8)0.0007 (9)
C170.0377 (13)0.0253 (10)0.0271 (13)0.0009 (9)0.0034 (10)−0.0034 (9)
C180.0347 (12)0.0370 (12)0.0297 (13)−0.0079 (10)0.0064 (10)0.0055 (10)
C190.0275 (10)0.0291 (10)0.0216 (11)0.0023 (8)0.0051 (9)0.0002 (9)
C200.0271 (11)0.0265 (10)0.0240 (12)−0.0010 (8)0.0008 (9)−0.0009 (9)
C210.0406 (13)0.0316 (12)0.0401 (15)0.0083 (10)0.0060 (12)0.0001 (11)
C220.0491 (15)0.0314 (12)0.0288 (14)0.0030 (11)0.0026 (11)0.0070 (10)
O1—C111.360 (3)C12—H12B0.9900
O1—C81.372 (3)C13—C141.470 (3)
O2—C131.346 (3)C14—C151.525 (3)
O2—C121.450 (3)C14—C161.540 (3)
O3—C131.197 (3)C14—H141.0000
C1—C21.377 (4)C15—C161.504 (3)
C1—C61.385 (3)C15—C181.505 (3)
C1—H10.9500C15—C171.508 (3)
C2—C31.363 (5)C16—C191.476 (3)
C2—H20.9500C16—H161.0000
C3—C41.379 (5)C17—H17A0.9800
C3—H30.9500C17—H17B0.9800
C4—C51.383 (4)C17—H17C0.9800
C4—H40.9500C18—H18A0.9800
C5—C61.384 (3)C18—H18B0.9800
C5—H50.9500C18—H18C0.9800
C6—C71.511 (3)C19—C201.327 (3)
C7—C81.486 (3)C19—H190.9500
C7—H7A0.9900C20—C211.495 (3)
C7—H7B0.9900C20—C221.501 (3)
C8—C91.344 (3)C21—H21A0.9800
C9—C101.437 (3)C21—H21B0.9800
C9—H90.9500C21—H21C0.9800
C10—C111.340 (3)C22—H22A0.9800
C10—C121.478 (3)C22—H22B0.9800
C11—H110.9500C22—H22C0.9800
C12—H12A0.9900
C11—O1—C8106.11 (18)C13—C14—C16117.97 (17)
C13—O2—C12117.90 (18)C15—C14—C1658.78 (13)
C2—C1—C6120.7 (3)C13—C14—H14115.1
C2—C1—H1119.7C15—C14—H14115.1
C6—C1—H1119.7C16—C14—H14115.1
C3—C2—C1120.2 (3)C16—C15—C18118.33 (18)
C3—C2—H2119.9C16—C15—C17119.24 (19)
C1—C2—H2119.9C18—C15—C17113.2 (2)
C2—C3—C4120.2 (3)C16—C15—C1461.09 (14)
C2—C3—H3119.9C18—C15—C14119.90 (19)
C4—C3—H3119.9C17—C15—C14115.70 (18)
C3—C4—C5119.7 (3)C19—C16—C15122.87 (18)
C3—C4—H4120.2C19—C16—C14118.61 (17)
C5—C4—H4120.2C15—C16—C1460.13 (14)
C4—C5—C6120.5 (3)C19—C16—H16114.8
C4—C5—H5119.7C15—C16—H16114.8
C6—C5—H5119.7C14—C16—H16114.8
C5—C6—C1118.6 (2)C15—C17—H17A109.5
C5—C6—C7120.7 (2)C15—C17—H17B109.5
C1—C6—C7120.7 (2)H17A—C17—H17B109.5
C8—C7—C6114.2 (2)C15—C17—H17C109.5
C8—C7—H7A108.7H17A—C17—H17C109.5
C6—C7—H7A108.7H17B—C17—H17C109.5
C8—C7—H7B108.7C15—C18—H18A109.5
C6—C7—H7B108.7C15—C18—H18B109.5
H7A—C7—H7B107.6H18A—C18—H18B109.5
C9—C8—O1110.07 (19)C15—C18—H18C109.5
C9—C8—C7133.7 (2)H18A—C18—H18C109.5
O1—C8—C7116.2 (2)H18B—C18—H18C109.5
C8—C9—C10106.8 (2)C20—C19—C16127.0 (2)
C8—C9—H9126.6C20—C19—H19116.5
C10—C9—H9126.6C16—C19—H19116.5
C11—C10—C9105.50 (19)C19—C20—C21124.8 (2)
C11—C10—C12127.2 (2)C19—C20—C22120.7 (2)
C9—C10—C12127.3 (2)C21—C20—C22114.5 (2)
C10—C11—O1111.5 (2)C20—C21—H21A109.5
C10—C11—H11124.2C20—C21—H21B109.5
O1—C11—H11124.2H21A—C21—H21B109.5
O2—C12—C10109.31 (18)C20—C21—H21C109.5
O2—C12—H12A109.8H21A—C21—H21C109.5
C10—C12—H12A109.8H21B—C21—H21C109.5
O2—C12—H12B109.8C20—C22—H22A109.5
C10—C12—H12B109.8C20—C22—H22B109.5
H12A—C12—H12B108.3H22A—C22—H22B109.5
O3—C13—O2123.6 (2)C20—C22—H22C109.5
O3—C13—C14126.8 (2)H22A—C22—H22C109.5
O2—C13—C14109.55 (17)H22B—C22—H22C109.5
C13—C14—C15122.92 (18)
C6—C1—C2—C30.2 (4)C12—O2—C13—O30.7 (3)
C1—C2—C3—C40.2 (4)C12—O2—C13—C14179.52 (18)
C2—C3—C4—C5−0.8 (4)O3—C13—C14—C15−37.8 (3)
C3—C4—C5—C61.1 (4)O2—C13—C14—C15143.42 (19)
C4—C5—C6—C1−0.8 (4)O3—C13—C14—C1631.4 (3)
C4—C5—C6—C7−180.0 (2)O2—C13—C14—C16−147.39 (18)
C2—C1—C6—C50.2 (3)C13—C14—C15—C16105.1 (2)
C2—C1—C6—C7179.3 (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—C8137.8 (2)C13—C14—C15—C17−144.2 (2)
C11—O1—C8—C91.3 (2)C16—C14—C15—C17110.7 (2)
C11—O1—C8—C7179.2 (2)C18—C15—C16—C19−142.9 (2)
C6—C7—C8—C9113.6 (3)C17—C15—C16—C191.7 (3)
C6—C7—C8—O1−63.7 (3)C14—C15—C16—C19106.6 (2)
O1—C8—C9—C10−1.1 (2)C18—C15—C16—C14110.4 (2)
C7—C8—C9—C10−178.5 (2)C17—C15—C16—C14−105.0 (2)
C8—C9—C10—C110.5 (2)C13—C14—C16—C19133.0 (2)
C8—C9—C10—C12−179.5 (2)C15—C14—C16—C19−113.6 (2)
C9—C10—C11—O10.3 (2)C13—C14—C16—C15−113.4 (2)
C12—C10—C11—O1−179.7 (2)C15—C16—C19—C20156.9 (2)
C8—O1—C11—C10−1.0 (3)C14—C16—C19—C20−131.9 (2)
C13—O2—C12—C10121.1 (2)C16—C19—C20—C21−0.2 (4)
C11—C10—C12—O2−123.2 (2)C16—C19—C20—C22178.4 (2)
C9—C10—C12—O256.8 (3)
D—H···AD—HH···AD···AD—H···A
C7—H7A···O3i0.992.713.516 (3)139
C11—H11···Cgii0.952.633.559 (3)167
Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C7—H7A⋯O3i 0.992.713.516 (3)139
C11—H11⋯Cg ii 0.952.633.559 (3)167

Symmetry codes: (i) ; (ii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Acrinathrin: (S)-cyano-(3-phen-oxy-phenyl)methyl (Z)-(1R,3S)-2,2-dimethyl-3-{2-[2,2,2-trifluoro-1-(trifluoro-methyl)eth-oxy-carbon-yl]vin-yl}cyclo-propane-1-carboxyl-ate.

Authors:  Hojin Yang; Tae Ho Kim; Ki-Min Park; Jineun Kim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-29
  2 in total

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