Literature DB >> 21754558

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.

Hojin Yang1, Tae Ho Kim, Ki-Min Park, Jineun Kim.   

Abstract

In the title compound, C(26)H(21)F(6)NO(5), the dihedral angle between the cyclo-propane ring plane and the vinyl group plane is 79.3 (3)°. The dihedral angle between the benzene and phenyl ring planes in the phen-oxy-benzyl group is 82.7 (1)°. In the crystal structure, weak inter-molecular C-H⋯π inter-actions and C-H⋯F hydrogen bonds contribute to the stabilization of the packing.

Entities:  

Year:  2011        PMID: 21754558      PMCID: PMC3089073          DOI: 10.1107/S1600536811014760

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: Vilchez et al. (1997 ▶). For related crystal structures, see: Owen (1976 ▶); Babin et al. (1992 ▶); Lei et al. (2001 ▶).

Experimental

Crystal data

C26H21F6NO5 M = 541.44 Orthorhombic, a = 7.4932 (2) Å b = 9.2679 (2) Å c = 36.9165 (8) Å V = 2563.71 (10) Å3 Z = 4 Mo Kα radiation μ = 0.13 mm−1 T = 173 K 0.17 × 0.14 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.984 24962 measured reflections 3634 independent reflections 2868 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.099 S = 1.06 3634 reflections 345 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.20 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014760/wn2431sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014760/wn2431Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H21F6NO5F(000) = 1112
Mr = 541.44Dx = 1.403 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6226 reflections
a = 7.4932 (2) Åθ = 2.3–23.1°
b = 9.2679 (2) ŵ = 0.13 mm1
c = 36.9165 (8) ÅT = 173 K
V = 2563.71 (10) Å3Plate, colourless
Z = 40.17 × 0.14 × 0.13 mm
Bruker APEXII CCD diffractometer3634 independent reflections
Radiation source: fine-focus sealed tube2868 reflections with I > 2σ(I)
graphiteRint = 0.042
φ and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→9
Tmin = 0.979, Tmax = 0.984k = −12→12
24962 measured reflectionsl = −49→42
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) = 0.099H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0327P)2 + 0.8807P] where P = (Fo2 + 2Fc2)/3
3634 reflections(Δ/σ)max = 0.001
345 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.20 e Å3
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
F10.9406 (3)0.7188 (4)0.39798 (7)0.1086 (9)
F20.8936 (3)0.6123 (3)0.44823 (6)0.0915 (7)
F30.9197 (3)0.8418 (3)0.44673 (7)0.0964 (8)
F40.5707 (4)0.6522 (2)0.47933 (5)0.0852 (7)
F50.5953 (4)0.8812 (2)0.47448 (6)0.1013 (9)
F60.3792 (3)0.7694 (3)0.44896 (7)0.0873 (7)
O10.6010 (3)0.61863 (19)0.40474 (5)0.0423 (5)
O20.4704 (3)0.7556 (2)0.36230 (5)0.0566 (6)
O30.3658 (3)0.3918 (2)0.25488 (5)0.0545 (6)
O40.3278 (2)0.57874 (18)0.21721 (4)0.0337 (4)
O5−0.0634 (2)0.6201 (3)0.10760 (5)0.0673 (8)
N10.7583 (4)0.5008 (3)0.20012 (6)0.0564 (7)
C10.8548 (5)0.7284 (4)0.42894 (10)0.0629 (9)
C20.5516 (5)0.7623 (4)0.45687 (9)0.0610 (9)
C30.6580 (4)0.7456 (3)0.42269 (7)0.0431 (7)
H30.63670.83090.40670.052*
C40.5049 (4)0.6380 (3)0.37320 (7)0.0375 (6)
C50.4624 (4)0.4984 (3)0.35754 (6)0.0412 (7)
H50.52420.41630.36650.049*
C60.3425 (4)0.4784 (3)0.33150 (6)0.0412 (7)
H60.33100.38320.32230.049*
C70.2268 (4)0.5881 (3)0.31574 (6)0.0366 (6)
H70.22380.68110.32950.044*
C80.0544 (4)0.5510 (3)0.29675 (7)0.0437 (7)
C90.2095 (4)0.6050 (3)0.27442 (6)0.0384 (6)
H90.19730.70700.26590.046*
C10−0.0072 (5)0.3963 (4)0.29394 (9)0.0660 (10)
H10B0.09540.33400.28880.099*
H10A−0.09470.38770.27430.099*
H10C−0.06220.36700.31690.099*
C11−0.0958 (4)0.6583 (4)0.30134 (9)0.0614 (9)
H11A−0.17670.65200.28050.092*
H11B−0.04650.75600.30290.092*
H11C−0.16170.63640.32360.092*
C120.3083 (4)0.5105 (3)0.24965 (6)0.0378 (6)
C130.4145 (3)0.4969 (3)0.18922 (6)0.0304 (5)
H130.37250.39460.19050.036*
C140.6090 (4)0.4999 (3)0.19511 (6)0.0394 (6)
C150.3567 (3)0.5607 (3)0.15333 (6)0.0278 (5)
C160.4784 (3)0.6086 (3)0.12799 (6)0.0314 (5)
H160.60280.60300.13280.038*
C170.4178 (3)0.6650 (3)0.09551 (6)0.0344 (6)
H170.50140.69830.07810.041*
C180.2380 (3)0.6735 (3)0.08809 (6)0.0339 (6)
H180.19720.71420.06600.041*
C190.1186 (3)0.6220 (3)0.11322 (7)0.0369 (6)
C200.1758 (3)0.5663 (3)0.14596 (6)0.0371 (6)
H200.09180.53210.16320.044*
C21−0.1298 (3)0.6912 (4)0.07707 (7)0.0426 (7)
C22−0.1479 (4)0.8371 (4)0.07716 (8)0.0487 (7)
H22−0.10690.89220.09720.058*
C23−0.2266 (4)0.9048 (4)0.04787 (9)0.0542 (8)
H23−0.23921.00680.04770.065*
C24−0.2859 (4)0.8259 (4)0.01934 (8)0.0506 (8)
H24−0.34140.8728−0.00060.061*
C25−0.2664 (4)0.6809 (4)0.01912 (8)0.0522 (8)
H25−0.30720.6267−0.00110.063*
C26−0.1869 (4)0.6104 (4)0.04824 (8)0.0501 (7)
H26−0.17270.50860.04810.060*
U11U22U33U12U13U23
F10.0654 (14)0.164 (3)0.0968 (17)−0.0054 (18)0.0156 (14)0.0000 (18)
F20.0805 (16)0.0831 (15)0.1108 (17)0.0176 (14)−0.0389 (14)0.0186 (14)
F30.0823 (16)0.0920 (17)0.1148 (18)−0.0321 (14)−0.0483 (15)0.0006 (15)
F40.128 (2)0.0805 (14)0.0467 (10)−0.0099 (15)0.0096 (13)0.0122 (11)
F50.148 (2)0.0745 (14)0.0815 (14)−0.0317 (17)0.0167 (16)−0.0427 (13)
F60.0680 (14)0.0754 (15)0.1185 (19)0.0067 (13)0.0178 (14)−0.0171 (15)
O10.0582 (12)0.0328 (9)0.0358 (9)0.0009 (10)−0.0143 (9)0.0010 (8)
O20.0780 (16)0.0350 (10)0.0567 (12)−0.0099 (11)−0.0328 (12)0.0126 (10)
O30.0876 (16)0.0437 (11)0.0322 (9)0.0203 (12)0.0059 (10)0.0060 (9)
O40.0429 (10)0.0363 (9)0.0220 (7)0.0062 (8)−0.0007 (7)0.0018 (7)
O50.0226 (9)0.124 (2)0.0551 (12)−0.0031 (13)−0.0015 (9)0.0512 (14)
N10.0415 (15)0.081 (2)0.0462 (14)0.0060 (15)−0.0110 (12)0.0057 (14)
C10.059 (2)0.066 (2)0.063 (2)−0.0061 (19)−0.0203 (18)0.0057 (19)
C20.079 (3)0.0510 (19)0.0535 (18)−0.007 (2)0.0002 (18)−0.0089 (17)
C30.0546 (17)0.0342 (13)0.0406 (14)−0.0057 (14)−0.0144 (13)0.0024 (13)
C40.0439 (16)0.0384 (14)0.0300 (12)−0.0039 (13)−0.0055 (12)0.0061 (11)
C50.0659 (19)0.0307 (12)0.0270 (12)−0.0002 (14)−0.0048 (13)0.0051 (11)
C60.0648 (19)0.0347 (13)0.0242 (12)−0.0046 (14)−0.0021 (13)−0.0011 (11)
C70.0490 (16)0.0368 (13)0.0240 (11)−0.0020 (12)0.0003 (11)−0.0044 (11)
C80.0476 (17)0.0554 (17)0.0281 (12)−0.0031 (15)−0.0002 (12)−0.0086 (12)
C90.0511 (16)0.0399 (13)0.0241 (11)0.0057 (14)−0.0019 (11)−0.0007 (11)
C100.067 (2)0.073 (2)0.0578 (19)−0.024 (2)−0.0022 (17)−0.0117 (18)
C110.0468 (18)0.086 (3)0.0518 (17)0.0070 (19)0.0022 (15)−0.0103 (18)
C120.0481 (16)0.0427 (14)0.0227 (11)0.0023 (13)−0.0032 (11)0.0012 (11)
C130.0318 (13)0.0351 (12)0.0242 (11)0.0028 (11)−0.0003 (10)0.0005 (10)
C140.0399 (16)0.0500 (16)0.0282 (12)0.0063 (14)−0.0058 (11)0.0014 (12)
C150.0297 (13)0.0301 (11)0.0236 (10)0.0003 (10)0.0002 (9)−0.0011 (9)
C160.0239 (12)0.0368 (12)0.0335 (12)0.0000 (11)−0.0007 (10)−0.0002 (11)
C170.0269 (13)0.0485 (15)0.0278 (12)−0.0017 (12)0.0062 (10)0.0069 (11)
C180.0309 (13)0.0482 (15)0.0225 (11)0.0012 (12)0.0000 (10)0.0056 (11)
C190.0219 (12)0.0547 (16)0.0342 (12)0.0003 (12)0.0003 (10)0.0084 (13)
C200.0265 (13)0.0551 (16)0.0295 (12)−0.0005 (12)0.0050 (10)0.0114 (12)
C210.0184 (12)0.073 (2)0.0368 (14)0.0001 (13)0.0015 (11)0.0218 (14)
C220.0356 (16)0.067 (2)0.0435 (15)−0.0086 (15)−0.0002 (13)−0.0039 (15)
C230.0386 (16)0.0540 (18)0.070 (2)0.0045 (15)0.0009 (15)0.0117 (17)
C240.0356 (16)0.075 (2)0.0418 (16)0.0067 (16)−0.0019 (13)0.0170 (16)
C250.0433 (17)0.079 (2)0.0344 (15)0.0005 (17)0.0020 (14)−0.0077 (15)
C260.0361 (15)0.0515 (16)0.0627 (19)0.0066 (15)0.0088 (14)0.0013 (16)
F1—C11.315 (4)C10—H10B0.9800
F2—C11.322 (4)C10—H10A0.9800
F3—C11.332 (4)C10—H10C0.9800
F4—C21.322 (4)C11—H11A0.9800
F5—C21.321 (4)C11—H11B0.9800
F6—C21.326 (4)C11—H11C0.9800
O1—C41.381 (3)C13—C141.474 (4)
O1—C31.416 (3)C13—C151.514 (3)
O2—C41.190 (3)C13—H131.0000
O3—C121.197 (3)C15—C161.380 (3)
O4—C121.362 (3)C15—C201.383 (4)
O4—C131.437 (3)C16—C171.385 (3)
O5—C191.380 (3)C16—H160.9500
O5—C211.397 (3)C17—C181.377 (4)
N1—C141.134 (4)C17—H170.9500
C1—C31.501 (5)C18—C191.374 (3)
C2—C31.500 (4)C18—H180.9500
C3—H31.0000C19—C201.383 (3)
C4—C51.453 (4)C20—H200.9500
C5—C61.329 (4)C21—C221.359 (4)
C5—H50.9500C21—C261.370 (4)
C6—C71.457 (4)C22—C231.382 (4)
C6—H60.9500C22—H220.9500
C7—C81.509 (4)C23—C241.357 (4)
C7—C91.539 (3)C23—H230.9500
C7—H71.0000C24—C251.352 (4)
C8—C101.509 (4)C24—H240.9500
C8—C91.510 (4)C25—C261.392 (4)
C8—C111.512 (4)C25—H250.9500
C9—C121.466 (4)C26—H260.9500
C9—H91.0000
C4—O1—C3116.3 (2)H10A—C10—H10C109.5
C12—O4—C13115.84 (19)C8—C11—H11A109.5
C19—O5—C21117.8 (2)C8—C11—H11B109.5
F1—C1—F2107.8 (3)H11A—C11—H11B109.5
F1—C1—F3107.7 (3)C8—C11—H11C109.5
F2—C1—F3107.2 (3)H11A—C11—H11C109.5
F1—C1—C3110.8 (3)H11B—C11—H11C109.5
F2—C1—C3112.7 (3)O3—C12—O4122.0 (2)
F3—C1—C3110.5 (3)O3—C12—C9129.0 (2)
F5—C2—F4108.0 (3)O4—C12—C9109.0 (2)
F5—C2—F6108.0 (3)O4—C13—C14109.3 (2)
F4—C2—F6106.4 (3)O4—C13—C15107.07 (18)
F5—C2—C3111.6 (3)C14—C13—C15113.9 (2)
F4—C2—C3113.0 (3)O4—C13—H13108.8
F6—C2—C3109.7 (3)C14—C13—H13108.8
O1—C3—C2108.6 (2)C15—C13—H13108.8
O1—C3—C1106.2 (3)N1—C14—C13178.9 (3)
C2—C3—C1113.8 (3)C16—C15—C20120.2 (2)
O1—C3—H3109.4C16—C15—C13122.0 (2)
C2—C3—H3109.4C20—C15—C13117.8 (2)
C1—C3—H3109.4C15—C16—C17119.4 (2)
O2—C4—O1121.2 (2)C15—C16—H16120.3
O2—C4—C5129.3 (2)C17—C16—H16120.3
O1—C4—C5109.5 (2)C18—C17—C16121.0 (2)
C6—C5—C4124.1 (3)C18—C17—H17119.5
C6—C5—H5118.0C16—C17—H17119.5
C4—C5—H5118.0C19—C18—C17118.9 (2)
C5—C6—C7126.4 (2)C19—C18—H18120.6
C5—C6—H6116.8C17—C18—H18120.6
C7—C6—H6116.8C18—C19—O5123.1 (2)
C6—C7—C8122.4 (2)C18—C19—C20121.2 (2)
C6—C7—C9121.1 (2)O5—C19—C20115.7 (2)
C8—C7—C959.36 (17)C19—C20—C15119.3 (2)
C6—C7—H7114.4C19—C20—H20120.3
C8—C7—H7114.4C15—C20—H20120.3
C9—C7—H7114.4C22—C21—C26121.0 (3)
C10—C8—C7120.7 (3)C22—C21—O5120.2 (3)
C10—C8—C9120.8 (3)C26—C21—O5118.7 (3)
C7—C8—C961.29 (18)C21—C22—C23119.5 (3)
C10—C8—C11113.9 (3)C21—C22—H22120.2
C7—C8—C11115.8 (2)C23—C22—H22120.2
C9—C8—C11114.6 (3)C24—C23—C22120.1 (3)
C12—C9—C8122.1 (2)C24—C23—H23119.9
C12—C9—C7121.0 (2)C22—C23—H23119.9
C8—C9—C759.35 (17)C25—C24—C23120.3 (3)
C12—C9—H9114.5C25—C24—H24119.8
C8—C9—H9114.5C23—C24—H24119.8
C7—C9—H9114.5C24—C25—C26120.5 (3)
C8—C10—H10B109.5C24—C25—H25119.7
C8—C10—H10A109.5C26—C25—H25119.7
H10B—C10—H10A109.5C21—C26—C25118.5 (3)
C8—C10—H10C109.5C21—C26—H26120.7
H10B—C10—H10C109.5C25—C26—H26120.7
C4—O1—C3—C2109.0 (3)C13—O4—C12—C9−176.9 (2)
C4—O1—C3—C1−128.2 (3)C8—C9—C12—O3−46.8 (4)
F5—C2—C3—O1−178.4 (3)C7—C9—C12—O324.2 (5)
F4—C2—C3—O159.8 (4)C8—C9—C12—O4132.7 (2)
F6—C2—C3—O1−58.8 (3)C7—C9—C12—O4−156.3 (2)
F5—C2—C3—C163.5 (4)C12—O4—C13—C14−79.2 (3)
F4—C2—C3—C1−58.3 (4)C12—O4—C13—C15157.0 (2)
F6—C2—C3—C1−176.8 (3)O4—C13—C14—N173 (21)
F1—C1—C3—O162.5 (4)C15—C13—C14—N1−167 (92)
F2—C1—C3—O1−58.3 (4)O4—C13—C15—C16124.6 (2)
F3—C1—C3—O1−178.3 (2)C14—C13—C15—C163.7 (3)
F1—C1—C3—C2−178.1 (3)O4—C13—C15—C20−57.2 (3)
F2—C1—C3—C261.1 (4)C14—C13—C15—C20−178.1 (3)
F3—C1—C3—C2−58.8 (4)C20—C15—C16—C171.3 (4)
C3—O1—C4—O2−1.1 (4)C13—C15—C16—C17179.5 (2)
C3—O1—C4—C5178.0 (2)C15—C16—C17—C18−0.2 (4)
O2—C4—C5—C6−15.1 (5)C16—C17—C18—C19−1.4 (4)
O1—C4—C5—C6166.0 (3)C17—C18—C19—O5−177.1 (3)
C4—C5—C6—C7−3.8 (5)C17—C18—C19—C201.9 (4)
C5—C6—C7—C8−157.7 (3)C21—O5—C19—C18−8.8 (5)
C5—C6—C7—C9131.1 (3)C21—O5—C19—C20172.2 (3)
C6—C7—C8—C101.1 (4)C18—C19—C20—C15−0.8 (5)
C9—C7—C8—C10110.8 (3)O5—C19—C20—C15178.3 (3)
C6—C7—C8—C9−109.6 (3)C16—C15—C20—C19−0.9 (4)
C6—C7—C8—C11145.2 (3)C13—C15—C20—C19−179.1 (2)
C9—C7—C8—C11−105.2 (3)C19—O5—C21—C22−78.7 (4)
C10—C8—C9—C12−1.0 (4)C19—O5—C21—C26105.6 (3)
C7—C8—C9—C12109.6 (3)C26—C21—C22—C230.5 (5)
C11—C8—C9—C12−143.3 (3)O5—C21—C22—C23−175.0 (2)
C10—C8—C9—C7−110.5 (3)C21—C22—C23—C240.3 (5)
C11—C8—C9—C7107.2 (3)C22—C23—C24—C25−0.9 (5)
C6—C7—C9—C120.3 (4)C23—C24—C25—C260.6 (5)
C8—C7—C9—C12−111.4 (3)C22—C21—C26—C25−0.8 (4)
C6—C7—C9—C8111.7 (3)O5—C21—C26—C25174.8 (2)
C13—O4—C12—O32.7 (4)C24—C25—C26—C210.2 (5)
Cg1 is the centroid of the C21–C26 phenyl ring.
D—H···AD—HH···AD···AD—H···A
C26—H26···F3i0.952.453.200 (4)135.
C17—H17···Cg1ii0.952.513.421 (1)161.
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C21–C26 phenyl ring.

D—H⋯AD—HH⋯ADAD—H⋯A
C26—H26⋯F3i0.952.453.200 (4)135
C17—H17⋯Cg1ii0.952.513.421 (1)161

Symmetry codes: (i) ; (ii) .

  3 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.  X-ray crystal structures of two pyrethroid insecticides: cis-3-phenoxybenzyl 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate and the 3-(2,2-dichlorovinyl) analogue.

Authors:  J D Owen
Journal:  J Chem Soc Perkin 1       Date:  1976

3.  Enols of amides. The effect of fluorine substituents in the ester groups of dicarboalkoxyanilidomethanes on the enol/amide and E-enol/Z-enol ratios. A multinuclei NMR study.

Authors:  Y X Lei; G Cerioni; Z Rappoport
Journal:  J Org Chem       Date:  2001-12-14       Impact factor: 4.354

  3 in total
  2 in total

1.  Crystal structure of fenpropathrin.

Authors:  Gihaeng Kang; Youngeun Jeon; Sangjin Lee; Tae Ho Kim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-11-19

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

Authors:  Tae Ho Kim; Ki-Min Park; Youngeun Jeon; Jineun Kim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-10-03
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.