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organic compounds
(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-N-(3-methoxyphenyl)-2,2-dimethylcyclopropanecarboxamide
aSchool of Materials Science and Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China
*Correspondence e-mail: yfytju@yahoo.com
The title compound, C16H17ClF3NO2, was synthesized from 3-[(E)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic acid and 3-methoxybenzenamine. The propenyl and carboxamide substituents lie on the same side of the cyclopropane ring plane, with the two methyl substituents on either side of the plane. The benzene ring makes a dihedral angle of 76.4 (3)° with the plane of the cyclopropane ring. The involves intermolecular N—H⋯O hydrogen bonds.
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997
); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997
); molecular graphics: SHELXTL (Bruker, 1997
); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536807063167/sf2011sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063167/sf2011Isup2.hkl
The title compound was prepared according to the method of Liu & Yan (2007). The product was recrystallized from acetone and ethyl acetate (9:1, v/v) over 2days at ambient temperature, giving colourless single crystals of (I), (E)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-N– (3-methoxyphenyl)-2,2-dimethylcyclopropanecarboxamide.
H atoms were positioned geometrically with C—H = 0.93–0.98 Å and refined using riding model with Uiso(H) = 1.2Ueq(carrier).The N—H hydrogen atom was located in a difference Fourier map and refined freely with an isotropic displacement parameter.
We reasoned that a structure containing both of 3-((E)-2-Chloro- 3,3,3-trifluoroprop-1-enyl)-2,2- dimethylcyclopropanecarboxylic acid and 3-methoxybenzenamine bioactive units may show enhanced insecticidal activity and prepared the title compound (I), Fig. 1. For preparation of the title compound, see: Liu & Yan (2007); and for the insecticidal properties of related compounds, see: Punja (1981). The propenyl and carboxamide substituents lie on the same side of the C4, C5, C6 cyclopropane ring plane, with the two methyl substituents, C7 and C8 on either side of this plane. The benzene ring system is essentially planar and makes a dihedral angle of 76.4 (3)° with the plane of the cyclopropane ring. The crystal packing of (I) is shown in Fig. 2 at the end of the Comment. The packing can be described as a dimeric arrangement of molecules linked through N—H···O···H—C hydrogen bond as shown in Fig. 2 and Table 1, the packing diagram also shows F and Cl interactions..
For related literature, see: Liu & Yan (2007); Punja (1981).
Data collection: SMART (Bruker, 1997); cell
SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997). ![]() | Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids. |
![]() | Fig. 2. The crystal structure of (I), viewed along c axis |
C16H17ClF3NO2 | Dx = 1.305 Mg m−3 |
Mr = 347.76 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pccn | Cell parameters from 2222 reflections |
a = 16.785 (2) Å | θ = 2.4–25.9° |
b = 22.246 (3) Å | µ = 0.25 mm−1 |
c = 9.4791 (12) Å | T = 294 K |
V = 3539.5 (8) Å3 | Block, colourless |
Z = 8 | 0.22 × 0.10 × 0.01 mm |
F(000) = 1440 |
Bruker SMART CCD area-detector diffractometer | 3119 independent reflections |
Radiation source: fine-focus sealed tube | 1325 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −16→19 |
Tmin = 0.947, Tmax = 0.998 | k = −26→26 |
16415 measured reflections | l = −11→8 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.236 | w = 1/[σ2(Fo2) + (0.P)2 + 13.2989P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3119 reflections | Δρmax = 0.69 e Å−3 |
216 parameters | Δρmin = −0.55 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (5) |
C16H17ClF3NO2 | V = 3539.5 (8) Å3 |
Mr = 347.76 | Z = 8 |
Orthorhombic, Pccn | Mo Kα radiation |
a = 16.785 (2) Å | µ = 0.25 mm−1 |
b = 22.246 (3) Å | T = 294 K |
c = 9.4791 (12) Å | 0.22 × 0.10 × 0.01 mm |
Bruker SMART CCD area-detector diffractometer | 3119 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1325 reflections with I > 2σ(I) |
Tmin = 0.947, Tmax = 0.998 | Rint = 0.081 |
16415 measured reflections |
R[F2 > 2σ(F2)] = 0.077 | 1 restraint |
wR(F2) = 0.236 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.P)2 + 13.2989P] where P = (Fo2 + 2Fc2)/3 |
3119 reflections | Δρmax = 0.69 e Å−3 |
216 parameters | Δρmin = −0.55 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.1468 (2) | 0.28489 (9) | 0.5467 (3) | 0.1433 (13) | |
C1 | 0.1084 (5) | 0.3528 (4) | 0.3245 (8) | 0.085 (2) | |
F1 | 0.0466 (4) | 0.3193 (3) | 0.2950 (5) | 0.160 (3) | |
F2 | 0.1668 (4) | 0.3302 (3) | 0.2454 (5) | 0.155 (2) | |
F3 | 0.0957 (4) | 0.4067 (2) | 0.2724 (4) | 0.129 (2) | |
O1 | 0.2154 (3) | 0.51918 (18) | 0.5554 (4) | 0.0682 (12) | |
O2 | 0.3834 (4) | 0.6927 (2) | 0.4146 (6) | 0.113 (2) | |
N1 | 0.2915 (3) | 0.5393 (2) | 0.7504 (5) | 0.0606 (14) | |
C2 | 0.1288 (4) | 0.3544 (3) | 0.4765 (7) | 0.0666 (18) | |
C3 | 0.1300 (4) | 0.4042 (3) | 0.5513 (6) | 0.0613 (16) | |
H3 | 0.1190 | 0.4400 | 0.5043 | 0.074* | |
C4 | 0.1473 (4) | 0.4082 (3) | 0.7024 (6) | 0.0652 (17) | |
H4 | 0.1538 | 0.3692 | 0.7492 | 0.078* | |
C5 | 0.1987 (4) | 0.4585 (3) | 0.7641 (6) | 0.0635 (17) | |
H5 | 0.2319 | 0.4457 | 0.8436 | 0.076* | |
C6 | 0.1101 (4) | 0.4567 (3) | 0.7950 (6) | 0.0722 (19) | |
C7 | 0.0558 (4) | 0.5034 (3) | 0.7319 (8) | 0.091 (2) | |
H7A | 0.0547 | 0.5382 | 0.7918 | 0.136* | |
H7B | 0.0030 | 0.4872 | 0.7234 | 0.136* | |
H7C | 0.0751 | 0.5146 | 0.6403 | 0.136* | |
C8 | 0.0874 (5) | 0.4372 (4) | 0.9438 (7) | 0.114 (3) | |
H8A | 0.1234 | 0.4065 | 0.9754 | 0.171* | |
H8B | 0.0340 | 0.4217 | 0.9437 | 0.171* | |
H8C | 0.0905 | 0.4711 | 1.0062 | 0.171* | |
C9 | 0.2344 (4) | 0.5077 (2) | 0.6786 (6) | 0.0558 (15) | |
C10 | 0.3371 (4) | 0.5896 (3) | 0.7084 (6) | 0.0598 (16) | |
C11 | 0.3868 (4) | 0.6149 (3) | 0.8111 (7) | 0.077 (2) | |
H11 | 0.3890 | 0.5983 | 0.9011 | 0.092* | |
C12 | 0.4326 (5) | 0.6643 (4) | 0.7784 (10) | 0.096 (3) | |
H12 | 0.4648 | 0.6815 | 0.8474 | 0.115* | |
C13 | 0.4313 (5) | 0.6888 (3) | 0.6451 (10) | 0.092 (2) | |
H13 | 0.4636 | 0.7215 | 0.6233 | 0.111* | |
C14 | 0.3815 (4) | 0.6643 (3) | 0.5434 (8) | 0.078 (2) | |
C15 | 0.3347 (4) | 0.6142 (3) | 0.5744 (7) | 0.0675 (18) | |
H15 | 0.3022 | 0.5974 | 0.5054 | 0.081* | |
C16 | 0.3299 (6) | 0.6743 (4) | 0.3071 (9) | 0.133 (4) | |
H16A | 0.3376 | 0.6323 | 0.2878 | 0.199* | |
H16B | 0.3398 | 0.6971 | 0.2230 | 0.199* | |
H16C | 0.2761 | 0.6809 | 0.3378 | 0.199* | |
H1 | 0.297 (4) | 0.529 (3) | 0.842 (2) | 0.09 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.222 (3) | 0.0645 (13) | 0.143 (2) | 0.0358 (16) | −0.034 (2) | −0.0058 (13) |
C1 | 0.108 (7) | 0.078 (5) | 0.071 (5) | −0.016 (5) | 0.004 (5) | −0.016 (4) |
F1 | 0.181 (6) | 0.187 (6) | 0.112 (4) | −0.107 (5) | −0.039 (4) | −0.009 (4) |
F2 | 0.177 (5) | 0.184 (6) | 0.105 (4) | −0.016 (5) | 0.042 (4) | −0.075 (4) |
F3 | 0.212 (6) | 0.118 (4) | 0.055 (3) | −0.006 (4) | −0.025 (3) | 0.001 (3) |
O1 | 0.090 (3) | 0.079 (3) | 0.036 (2) | −0.016 (2) | −0.003 (2) | 0.007 (2) |
O2 | 0.116 (5) | 0.107 (4) | 0.116 (5) | −0.055 (4) | −0.012 (4) | 0.031 (4) |
N1 | 0.077 (4) | 0.062 (3) | 0.043 (3) | −0.008 (3) | −0.003 (3) | 0.000 (3) |
C2 | 0.076 (5) | 0.061 (4) | 0.063 (4) | 0.003 (3) | 0.000 (3) | −0.003 (3) |
C3 | 0.077 (5) | 0.059 (4) | 0.048 (3) | −0.005 (3) | 0.003 (3) | 0.004 (3) |
C4 | 0.086 (5) | 0.059 (4) | 0.051 (3) | −0.007 (4) | 0.003 (3) | 0.002 (3) |
C5 | 0.084 (5) | 0.070 (4) | 0.037 (3) | −0.013 (4) | −0.003 (3) | 0.006 (3) |
C6 | 0.093 (5) | 0.078 (5) | 0.046 (3) | −0.016 (4) | 0.020 (4) | −0.003 (3) |
C7 | 0.078 (5) | 0.087 (5) | 0.107 (6) | −0.005 (4) | 0.016 (5) | −0.022 (5) |
C8 | 0.148 (8) | 0.139 (7) | 0.054 (4) | −0.057 (6) | 0.037 (5) | −0.013 (5) |
C9 | 0.070 (4) | 0.056 (4) | 0.042 (3) | −0.003 (3) | 0.006 (3) | 0.000 (3) |
C10 | 0.061 (4) | 0.057 (4) | 0.061 (4) | 0.000 (3) | −0.004 (3) | −0.006 (3) |
C11 | 0.079 (5) | 0.078 (5) | 0.074 (5) | −0.002 (4) | −0.012 (4) | −0.014 (4) |
C12 | 0.081 (6) | 0.081 (6) | 0.126 (8) | −0.012 (5) | −0.018 (5) | −0.025 (5) |
C13 | 0.082 (6) | 0.075 (5) | 0.120 (7) | −0.019 (4) | −0.008 (5) | −0.005 (5) |
C14 | 0.076 (5) | 0.067 (4) | 0.091 (5) | −0.012 (4) | −0.006 (4) | 0.005 (4) |
C15 | 0.078 (5) | 0.062 (4) | 0.063 (4) | −0.015 (4) | 0.001 (3) | −0.002 (3) |
C16 | 0.160 (9) | 0.130 (8) | 0.109 (7) | −0.060 (7) | −0.034 (7) | 0.041 (6) |
Cl1—C2 | 1.710 (6) | C6—C8 | 1.524 (8) |
C1—F1 | 1.308 (8) | C7—H7A | 0.9600 |
C1—F3 | 1.314 (8) | C7—H7B | 0.9600 |
C1—F2 | 1.333 (9) | C7—H7C | 0.9600 |
C1—C2 | 1.481 (9) | C8—H8A | 0.9600 |
O1—C9 | 1.238 (6) | C8—H8B | 0.9600 |
O2—C14 | 1.375 (8) | C8—H8C | 0.9600 |
O2—C16 | 1.419 (9) | C10—C15 | 1.383 (8) |
N1—C9 | 1.370 (7) | C10—C11 | 1.401 (8) |
N1—C10 | 1.412 (7) | C11—C12 | 1.377 (10) |
N1—H1 | 0.901 (10) | C11—H11 | 0.9300 |
C2—C3 | 1.316 (8) | C12—C13 | 1.377 (10) |
C3—C4 | 1.464 (8) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.388 (9) |
C4—C6 | 1.524 (9) | C13—H13 | 0.9300 |
C4—C5 | 1.530 (8) | C14—C15 | 1.396 (8) |
C4—H4 | 0.9800 | C15—H15 | 0.9300 |
C5—C9 | 1.487 (7) | C16—H16A | 0.9600 |
C5—C6 | 1.516 (9) | C16—H16B | 0.9600 |
C5—H5 | 0.9800 | C16—H16C | 0.9600 |
C6—C7 | 1.506 (9) | ||
F1—C1—F3 | 108.1 (8) | C6—C7—H7C | 109.5 |
F1—C1—F2 | 104.3 (6) | H7A—C7—H7C | 109.5 |
F3—C1—F2 | 104.6 (7) | H7B—C7—H7C | 109.5 |
F1—C1—C2 | 113.9 (7) | C6—C8—H8A | 109.5 |
F3—C1—C2 | 112.5 (6) | C6—C8—H8B | 109.5 |
F2—C1—C2 | 112.8 (7) | H8A—C8—H8B | 109.5 |
C14—O2—C16 | 119.3 (6) | C6—C8—H8C | 109.5 |
C9—N1—C10 | 130.2 (5) | H8A—C8—H8C | 109.5 |
C9—N1—H1 | 114 (4) | H8B—C8—H8C | 109.5 |
C10—N1—H1 | 115 (4) | O1—C9—N1 | 122.8 (5) |
C3—C2—C1 | 123.2 (6) | O1—C9—C5 | 124.2 (6) |
C3—C2—Cl1 | 123.3 (5) | N1—C9—C5 | 113.0 (5) |
C1—C2—Cl1 | 113.4 (5) | C15—C10—C11 | 119.8 (6) |
C2—C3—C4 | 125.5 (6) | C15—C10—N1 | 123.8 (6) |
C2—C3—H3 | 117.2 | C11—C10—N1 | 116.4 (6) |
C4—C3—H3 | 117.2 | C12—C11—C10 | 119.7 (7) |
C3—C4—C6 | 121.6 (6) | C12—C11—H11 | 120.1 |
C3—C4—C5 | 122.0 (5) | C10—C11—H11 | 120.1 |
C6—C4—C5 | 59.5 (4) | C13—C12—C11 | 121.0 (7) |
C3—C4—H4 | 114.3 | C13—C12—H12 | 119.5 |
C6—C4—H4 | 114.3 | C11—C12—H12 | 119.5 |
C5—C4—H4 | 114.3 | C12—C13—C14 | 119.4 (7) |
C9—C5—C6 | 121.4 (6) | C12—C13—H13 | 120.3 |
C9—C5—C4 | 123.9 (5) | C14—C13—H13 | 120.3 |
C6—C5—C4 | 60.1 (4) | O2—C14—C13 | 115.0 (7) |
C9—C5—H5 | 113.7 | O2—C14—C15 | 124.6 (7) |
C6—C5—H5 | 113.7 | C13—C14—C15 | 120.5 (7) |
C4—C5—H5 | 113.7 | C10—C15—C14 | 119.5 (6) |
C7—C6—C5 | 119.9 (6) | C10—C15—H15 | 120.2 |
C7—C6—C4 | 120.5 (6) | C14—C15—H15 | 120.2 |
C5—C6—C4 | 60.4 (4) | O2—C16—H16A | 109.5 |
C7—C6—C8 | 114.4 (7) | O2—C16—H16B | 109.5 |
C5—C6—C8 | 115.5 (6) | H16A—C16—H16B | 109.5 |
C4—C6—C8 | 115.7 (6) | O2—C16—H16C | 109.5 |
C6—C7—H7A | 109.5 | H16A—C16—H16C | 109.5 |
C6—C7—H7B | 109.5 | H16B—C16—H16C | 109.5 |
H7A—C7—H7B | 109.5 | ||
F1—C1—C2—C3 | −120.4 (8) | C5—C4—C6—C8 | −106.1 (7) |
F3—C1—C2—C3 | 3.0 (11) | C10—N1—C9—O1 | 2.2 (10) |
F2—C1—C2—C3 | 121.0 (8) | C10—N1—C9—C5 | −178.0 (6) |
F1—C1—C2—Cl1 | 57.3 (9) | C6—C5—C9—O1 | −59.5 (8) |
F3—C1—C2—Cl1 | −179.3 (6) | C4—C5—C9—O1 | 13.4 (10) |
F2—C1—C2—Cl1 | −61.3 (8) | C6—C5—C9—N1 | 120.7 (6) |
C1—C2—C3—C4 | 178.0 (7) | C4—C5—C9—N1 | −166.4 (6) |
Cl1—C2—C3—C4 | 0.6 (10) | C9—N1—C10—C15 | −4.8 (10) |
C2—C3—C4—C6 | −149.2 (7) | C9—N1—C10—C11 | 175.1 (6) |
C2—C3—C4—C5 | 139.4 (7) | C15—C10—C11—C12 | 0.5 (10) |
C3—C4—C5—C9 | 0.8 (10) | N1—C10—C11—C12 | −179.4 (6) |
C6—C4—C5—C9 | −109.7 (7) | C10—C11—C12—C13 | −1.2 (12) |
C3—C4—C5—C6 | 110.5 (7) | C11—C12—C13—C14 | 1.8 (13) |
C9—C5—C6—C7 | 3.4 (9) | C16—O2—C14—C13 | −174.8 (8) |
C4—C5—C6—C7 | −110.3 (7) | C16—O2—C14—C15 | 5.7 (12) |
C9—C5—C6—C4 | 113.7 (6) | C12—C13—C14—O2 | 178.7 (7) |
C9—C5—C6—C8 | −139.9 (6) | C12—C13—C14—C15 | −1.8 (12) |
C4—C5—C6—C8 | 106.4 (7) | C11—C10—C15—C14 | −0.5 (10) |
C3—C4—C6—C7 | −1.8 (9) | N1—C10—C15—C14 | 179.4 (6) |
C5—C4—C6—C7 | 109.3 (7) | O2—C14—C15—C10 | −179.4 (7) |
C3—C4—C6—C5 | −111.0 (6) | C13—C14—C15—C10 | 1.2 (11) |
C3—C4—C6—C8 | 142.9 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.90 (1) | 2.05 (2) | 2.928 (6) | 166 (6) |
Symmetry code: (i) −x+1/2, y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H17ClF3NO2 |
Mr | 347.76 |
Crystal system, space group | Orthorhombic, Pccn |
Temperature (K) | 294 |
a, b, c (Å) | 16.785 (2), 22.246 (3), 9.4791 (12) |
V (Å3) | 3539.5 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.22 × 0.10 × 0.01 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.947, 0.998 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16415, 3119, 1325 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.236, 1.02 |
No. of reflections | 3119 |
No. of parameters | 216 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.P)2 + 13.2989P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.69, −0.55 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.901 (10) | 2.046 (19) | 2.928 (6) | 166 (6) |
Symmetry code: (i) −x+1/2, y, z+1/2. |
Acknowledgements
This work was supported by the National Natural Science Foundation (No. 20376059) and Tianjin Polytechnic University.
References
Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, D.-Q. & Yan, F.-Y. (2007). Acta Cryst. E63, o4202. Web of Science CSD CrossRef IUCr Journals Google Scholar
Punja, N. (1981). European Patent EP 0031199. Google Scholar
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We reasoned that a structure containing both of 3-((E)-2-Chloro- 3,3,3-trifluoroprop-1-enyl)-2,2- dimethylcyclopropanecarboxylic acid and 3-methoxybenzenamine bioactive units may show enhanced insecticidal activity and prepared the title compound (I), Fig. 1. For preparation of the title compound, see: Liu & Yan (2007); and for the insecticidal properties of related compounds, see: Punja (1981). The propenyl and carboxamide substituents lie on the same side of the C4, C5, C6 cyclopropane ring plane, with the two methyl substituents, C7 and C8 on either side of this plane. The benzene ring system is essentially planar and makes a dihedral angle of 76.4 (3)° with the plane of the cyclopropane ring. The crystal packing of (I) is shown in Fig. 2 at the end of the Comment. The packing can be described as a dimeric arrangement of molecules linked through N—H···O···H—C hydrogen bond as shown in Fig. 2 and Table 1, the packing diagram also shows F and Cl interactions..