Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045916/bv2066sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045916/bv2066Isup2.hkl |
CCDC reference: 667268
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.011 Å
- R factor = 0.054
- wR factor = 0.205
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT213_ALERT_2_C Atom C8 has ADP max/min Ratio ............. 3.10 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C4 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C6 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2- dimethylcyclopropanecarboxylic acid (0.97 g, 4.0 mmol) was dispersed in SOCl2 (15 ml), and a drop of anhydrous DMF was added. The mixture was heated to reflux for 4 h. SOCl2 was removed by rotoevaporation. The crude product could be directly disolved in anhydrous toluene, already mixed with 2-bromoaniline (0.71 g, 4.1 mmol). Triethylamine was aded droppwise to the system to prevent white fumes coming out. After 12 h stirring at room temperature, the reaction mixture was treated with hexane. Recrystallization of the off-white product from methanol and a small amount of water (50:1) overnight at ambient temperature gave colorless single crystals of (E)—N-(2-bromophenyl)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2, 2-dimethylcyclopropanecarboxamide, suitable for X-ray analysis.
H atoms were positioned geometrically with C—H = 0.93–0.98 Å and refined using riding model with Uiso(H) = 1.2Ueq(carrier). H atom of N—H was located from difference map and refined freely.
3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate for tefluthrin, a important insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja 1981). Bromine containing pesticides have the advantage of low toxicity, high activity and low residues (Zhang 2005). The present structure contains two active parts and thus might be expected to show some insecticide activity. The X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound, (I) In this paper, the title compound, (E)—N-(2-bromophenyl)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2, 2-dimethylcyclopropanecarboxamide, (I), was synthesized and its structure is illustrated in Fig. 1. The dihedral angle between the benzene moiety and the cyclopropane group is 76.3 (3)°. The amide hydrogen and methine hydrogen link with the same amide oxygen in an adjacent molecule via an intermolecular N—H···O···H—C hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N—H···O···H—C hydrogen bonds as shown in Fig. 2 and Table 1.
For related literature, see: Punja (1981); Zhang (2005).
Data collection: SMART (Bruker, 1997); cell refinement: SMART (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. H atoms are drawn as spheres of arbitrary radius. | |
Fig. 2. The crystal structure of (I), viewed along a axis |
C15H14BrClF3NO | Dx = 1.546 Mg m−3 |
Mr = 396.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 2447 reflections |
a = 18.701 (3) Å | θ = 2.4–19.3° |
b = 9.4180 (16) Å | µ = 2.60 mm−1 |
c = 19.356 (3) Å | T = 294 K |
V = 3409.2 (10) Å3 | Prism, colourless |
Z = 8 | 0.24 × 0.22 × 0.18 mm |
F(000) = 1584 |
Bruker SMART CCD area-detector diffractometer | 3004 independent reflections |
Radiation source: fine-focus sealed tube | 1493 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −19→22 |
Tmin = 0.575, Tmax = 0.652 | k = −9→11 |
16318 measured reflections | l = −17→23 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.205 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0915P)2 + 5.7059P] where P = (Fo2 + 2Fc2)/3 |
3004 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.46 e Å−3 |
6 restraints | Δρmin = −0.71 e Å−3 |
C15H14BrClF3NO | V = 3409.2 (10) Å3 |
Mr = 396.63 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 18.701 (3) Å | µ = 2.60 mm−1 |
b = 9.4180 (16) Å | T = 294 K |
c = 19.356 (3) Å | 0.24 × 0.22 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 3004 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1493 reflections with I > 2σ(I) |
Tmin = 0.575, Tmax = 0.652 | Rint = 0.075 |
16318 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 6 restraints |
wR(F2) = 0.205 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.46 e Å−3 |
3004 reflections | Δρmin = −0.71 e Å−3 |
201 parameters |
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 | ||
Br1 | 0.05485 (5) | −0.07635 (11) | 0.13989 (5) | 0.0912 (4) | |
Cl1 | 0.34565 (12) | 0.1240 (3) | 0.44233 (11) | 0.0843 (7) | |
F1 | 0.3114 (3) | 0.4319 (6) | 0.4070 (3) | 0.1145 (19) | |
F2 | 0.4226 (3) | 0.4018 (5) | 0.4192 (3) | 0.1077 (18) | |
F3 | 0.3800 (3) | 0.4432 (4) | 0.3209 (3) | 0.1038 (18) | |
O1 | 0.2896 (2) | 0.1847 (4) | 0.1711 (3) | 0.0588 (13) | |
N1 | 0.2144 (3) | 0.0086 (5) | 0.1403 (3) | 0.0464 (13) | |
H1 | 0.2044 | −0.0797 | 0.1461 | 0.056* | |
C1 | 0.3690 (4) | 0.3721 (9) | 0.3778 (5) | 0.070 (2) | |
C2 | 0.3568 (3) | 0.2181 (7) | 0.3663 (4) | 0.0515 (17) | |
C3 | 0.3552 (4) | 0.1605 (7) | 0.3053 (4) | 0.0552 (18) | |
H3 | 0.3631 | 0.2197 | 0.2676 | 0.066* | |
C4 | 0.3420 (4) | 0.0089 (7) | 0.2909 (4) | 0.061 (2) | |
H4 | 0.3343 | −0.0487 | 0.3324 | 0.073* | |
C5 | 0.3773 (4) | −0.0685 (7) | 0.2336 (4) | 0.070 (2) | |
C6 | 0.2990 (4) | −0.0395 (6) | 0.2287 (4) | 0.0567 (19) | |
H6 | 0.2687 | −0.1226 | 0.2374 | 0.068* | |
C7 | 0.4275 (4) | 0.0051 (12) | 0.1865 (5) | 0.099 (3) | |
H7A | 0.4270 | −0.0407 | 0.1422 | 0.148* | |
H7B | 0.4749 | 0.0013 | 0.2054 | 0.148* | |
H7C | 0.4132 | 0.1024 | 0.1813 | 0.148* | |
C8 | 0.3977 (5) | −0.2211 (8) | 0.2502 (6) | 0.120 (4) | |
H8A | 0.4153 | −0.2666 | 0.2092 | 0.180* | |
H8B | 0.3565 | −0.2712 | 0.2669 | 0.180* | |
H8C | 0.4343 | −0.2217 | 0.2850 | 0.180* | |
C9 | 0.2686 (3) | 0.0626 (6) | 0.1782 (3) | 0.0464 (15) | |
C10 | 0.1729 (3) | 0.0846 (7) | 0.0919 (3) | 0.0479 (16) | |
C11 | 0.2031 (4) | 0.1875 (8) | 0.0496 (4) | 0.069 (2) | |
H11 | 0.2520 | 0.2049 | 0.0519 | 0.083* | |
C12 | 0.1613 (5) | 0.2639 (9) | 0.0045 (5) | 0.088 (3) | |
H12 | 0.1826 | 0.3307 | −0.0243 | 0.106* | |
C13 | 0.0887 (5) | 0.2433 (10) | 0.0011 (5) | 0.091 (3) | |
H13 | 0.0607 | 0.2990 | −0.0279 | 0.109* | |
C14 | 0.0579 (4) | 0.1393 (9) | 0.0411 (4) | 0.071 (2) | |
H14 | 0.0092 | 0.1212 | 0.0379 | 0.086* | |
C15 | 0.0995 (3) | 0.0624 (7) | 0.0859 (3) | 0.0514 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0698 (6) | 0.1091 (8) | 0.0947 (8) | −0.0272 (5) | −0.0041 (5) | 0.0263 (5) |
Cl1 | 0.0942 (16) | 0.0951 (16) | 0.0636 (13) | −0.0040 (13) | 0.0020 (11) | 0.0041 (11) |
F1 | 0.110 (3) | 0.095 (3) | 0.139 (4) | 0.022 (3) | 0.014 (3) | −0.040 (3) |
F2 | 0.103 (4) | 0.089 (4) | 0.130 (5) | −0.012 (3) | −0.040 (4) | −0.035 (3) |
F3 | 0.161 (5) | 0.042 (2) | 0.109 (4) | −0.022 (3) | 0.000 (4) | −0.007 (3) |
O1 | 0.064 (3) | 0.034 (3) | 0.078 (3) | −0.004 (2) | −0.016 (3) | 0.003 (2) |
N1 | 0.048 (3) | 0.035 (3) | 0.056 (3) | 0.001 (2) | −0.005 (3) | 0.003 (3) |
C1 | 0.064 (5) | 0.060 (5) | 0.086 (6) | 0.005 (4) | 0.000 (5) | −0.021 (5) |
C2 | 0.046 (4) | 0.049 (4) | 0.060 (5) | 0.000 (3) | 0.000 (3) | −0.002 (3) |
C3 | 0.073 (5) | 0.041 (4) | 0.052 (4) | 0.004 (3) | −0.004 (4) | 0.002 (3) |
C4 | 0.086 (5) | 0.032 (4) | 0.065 (5) | −0.002 (4) | −0.027 (4) | −0.002 (3) |
C5 | 0.080 (6) | 0.043 (4) | 0.086 (6) | 0.018 (4) | −0.031 (5) | −0.022 (4) |
C6 | 0.066 (5) | 0.031 (3) | 0.073 (5) | −0.002 (3) | −0.021 (4) | 0.002 (3) |
C7 | 0.068 (6) | 0.118 (8) | 0.109 (8) | 0.032 (6) | −0.015 (6) | −0.049 (7) |
C8 | 0.148 (9) | 0.046 (5) | 0.166 (10) | 0.046 (5) | −0.098 (8) | −0.044 (6) |
C9 | 0.044 (4) | 0.036 (4) | 0.059 (4) | 0.003 (3) | 0.002 (3) | −0.005 (3) |
C10 | 0.053 (4) | 0.045 (4) | 0.046 (4) | 0.002 (3) | −0.003 (3) | 0.001 (3) |
C11 | 0.062 (5) | 0.076 (5) | 0.069 (5) | −0.009 (4) | −0.004 (4) | 0.025 (4) |
C12 | 0.103 (7) | 0.077 (6) | 0.085 (6) | −0.012 (5) | −0.020 (5) | 0.038 (5) |
C13 | 0.089 (6) | 0.081 (6) | 0.102 (7) | 0.006 (6) | −0.033 (6) | 0.026 (5) |
C14 | 0.062 (5) | 0.080 (5) | 0.073 (5) | 0.007 (4) | −0.013 (4) | 0.001 (5) |
C15 | 0.048 (4) | 0.054 (4) | 0.053 (4) | 0.002 (3) | 0.001 (3) | −0.004 (3) |
Br1—C15 | 1.870 (7) | C6—C9 | 1.484 (9) |
Cl1—C2 | 1.730 (7) | C6—H6 | 0.9800 |
F1—C1 | 1.341 (9) | C7—H7A | 0.9600 |
F2—C1 | 1.313 (9) | C7—H7B | 0.9600 |
F3—C1 | 1.306 (10) | C7—H7C | 0.9600 |
O1—C9 | 1.223 (7) | C8—H8A | 0.9600 |
N1—C9 | 1.351 (8) | C8—H8B | 0.9600 |
N1—C10 | 1.412 (8) | C8—H8C | 0.9600 |
N1—H1 | 0.8600 | C10—C11 | 1.389 (9) |
C1—C2 | 1.485 (10) | C10—C15 | 1.393 (9) |
C2—C3 | 1.300 (9) | C11—C12 | 1.375 (10) |
C3—C4 | 1.475 (9) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.373 (11) |
C4—C5 | 1.482 (11) | C12—H12 | 0.9300 |
C4—C6 | 1.518 (9) | C13—C14 | 1.375 (11) |
C4—H4 | 0.9800 | C13—H13 | 0.9300 |
C5—C7 | 1.482 (13) | C14—C15 | 1.370 (10) |
C5—C6 | 1.492 (10) | C14—H14 | 0.9300 |
C5—C8 | 1.521 (10) | ||
C9—N1—C10 | 125.7 (5) | C5—C7—H7A | 109.5 |
C9—N1—H1 | 117.2 | C5—C7—H7B | 109.5 |
C10—N1—H1 | 117.2 | H7A—C7—H7B | 109.5 |
F3—C1—F2 | 106.6 (7) | C5—C7—H7C | 109.5 |
F3—C1—F1 | 105.5 (7) | H7A—C7—H7C | 109.5 |
F2—C1—F1 | 105.5 (7) | H7B—C7—H7C | 109.5 |
F3—C1—C2 | 113.4 (7) | C5—C8—H8A | 109.5 |
F2—C1—C2 | 114.6 (7) | C5—C8—H8B | 109.5 |
F1—C1—C2 | 110.5 (7) | H8A—C8—H8B | 109.5 |
C3—C2—C1 | 123.2 (7) | C5—C8—H8C | 109.5 |
C3—C2—Cl1 | 123.8 (5) | H8A—C8—H8C | 109.5 |
C1—C2—Cl1 | 113.0 (6) | H8B—C8—H8C | 109.5 |
C2—C3—C4 | 125.4 (7) | O1—C9—N1 | 122.3 (6) |
C2—C3—H3 | 117.3 | O1—C9—C6 | 124.1 (6) |
C4—C3—H3 | 117.3 | N1—C9—C6 | 113.6 (5) |
C3—C4—C5 | 122.9 (7) | C11—C10—C15 | 117.2 (6) |
C3—C4—C6 | 122.0 (6) | C11—C10—N1 | 121.3 (6) |
C5—C4—C6 | 59.6 (5) | C15—C10—N1 | 121.4 (6) |
C3—C4—H4 | 113.9 | C12—C11—C10 | 120.5 (7) |
C5—C4—H4 | 113.9 | C12—C11—H11 | 119.8 |
C6—C4—H4 | 113.9 | C10—C11—H11 | 119.8 |
C7—C5—C4 | 120.8 (6) | C13—C12—C11 | 121.3 (8) |
C7—C5—C6 | 119.8 (7) | C13—C12—H12 | 119.4 |
C4—C5—C6 | 61.4 (5) | C11—C12—H12 | 119.4 |
C7—C5—C8 | 114.4 (8) | C12—C13—C14 | 119.2 (8) |
C4—C5—C8 | 114.8 (8) | C12—C13—H13 | 120.4 |
C6—C5—C8 | 115.7 (7) | C14—C13—H13 | 120.4 |
C9—C6—C5 | 122.4 (6) | C15—C14—C13 | 119.7 (7) |
C9—C6—C4 | 122.0 (5) | C15—C14—H14 | 120.2 |
C5—C6—C4 | 59.0 (5) | C13—C14—H14 | 120.2 |
C9—C6—H6 | 114.2 | C14—C15—C10 | 122.1 (7) |
C5—C6—H6 | 114.2 | C14—C15—Br1 | 118.0 (5) |
C4—C6—H6 | 114.2 | C10—C15—Br1 | 119.9 (5) |
F3—C1—C2—C3 | −1.8 (11) | C5—C4—C6—C9 | −111.2 (8) |
F2—C1—C2—C3 | −124.6 (8) | C3—C4—C6—C5 | 112.1 (8) |
F1—C1—C2—C3 | 116.4 (9) | C10—N1—C9—O1 | −4.1 (10) |
F3—C1—C2—Cl1 | 177.7 (5) | C10—N1—C9—C6 | 175.6 (6) |
F2—C1—C2—Cl1 | 54.9 (9) | C5—C6—C9—O1 | −51.3 (10) |
F1—C1—C2—Cl1 | −64.1 (8) | C4—C6—C9—O1 | 19.8 (11) |
C1—C2—C3—C4 | −178.8 (7) | C5—C6—C9—N1 | 129.0 (6) |
Cl1—C2—C3—C4 | 1.7 (11) | C4—C6—C9—N1 | −159.9 (6) |
C2—C3—C4—C5 | −144.9 (7) | C9—N1—C10—C11 | 37.4 (10) |
C2—C3—C4—C6 | 142.9 (8) | C9—N1—C10—C15 | −140.7 (7) |
C3—C4—C5—C7 | −1.1 (11) | C15—C10—C11—C12 | 0.5 (11) |
C6—C4—C5—C7 | 109.5 (8) | N1—C10—C11—C12 | −177.7 (7) |
C3—C4—C5—C6 | −110.7 (7) | C10—C11—C12—C13 | 1.6 (14) |
C3—C4—C5—C8 | 142.4 (7) | C11—C12—C13—C14 | −3.4 (15) |
C6—C4—C5—C8 | −107.0 (7) | C12—C13—C14—C15 | 2.9 (14) |
C7—C5—C6—C9 | −0.6 (10) | C13—C14—C15—C10 | −0.8 (12) |
C4—C5—C6—C9 | 110.5 (7) | C13—C14—C15—Br1 | 179.3 (7) |
C8—C5—C6—C9 | −144.0 (8) | C11—C10—C15—C14 | −0.9 (10) |
C7—C5—C6—C4 | −111.1 (8) | N1—C10—C15—C14 | 177.3 (6) |
C8—C5—C6—C4 | 105.5 (8) | C11—C10—C15—Br1 | 179.0 (5) |
C3—C4—C6—C9 | 0.9 (11) | N1—C10—C15—Br1 | −2.8 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.27 | 3.110 (7) | 164 |
C6—H6···01i | 0.98 | 2.48 | 2.39 | 137 |
Symmetry code: (i) −x+1/2, y−1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C15H14BrClF3NO |
Mr | 396.63 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 294 |
a, b, c (Å) | 18.701 (3), 9.4180 (16), 19.356 (3) |
V (Å3) | 3409.2 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.60 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.575, 0.652 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16318, 3004, 1493 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.205, 1.04 |
No. of reflections | 3004 |
No. of parameters | 201 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.71 |
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 | 0.86 | 2.27 | 3.110 (7) | 163.9 |
C6—H6···01i | 0.98 | 2.48 | 2.39 | 137 |
Symmetry code: (i) −x+1/2, y−1/2, z. |
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3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate for tefluthrin, a important insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja 1981). Bromine containing pesticides have the advantage of low toxicity, high activity and low residues (Zhang 2005). The present structure contains two active parts and thus might be expected to show some insecticide activity. The X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound, (I) In this paper, the title compound, (E)—N-(2-bromophenyl)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2, 2-dimethylcyclopropanecarboxamide, (I), was synthesized and its structure is illustrated in Fig. 1. The dihedral angle between the benzene moiety and the cyclopropane group is 76.3 (3)°. The amide hydrogen and methine hydrogen link with the same amide oxygen in an adjacent molecule via an intermolecular N—H···O···H—C hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N—H···O···H—C hydrogen bonds as shown in Fig. 2 and Table 1.