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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o61
https://doi.org/10.1107/S1600536810050634

3-[(E)-2-Chloro-3,3,3-tri­fluoro­prop-1-en-1-yl]-N-(2-chloro­phen­yl)-2,2-di­methyl­cyclo­propane-1-carboxamide

Dong-Qing Liu,a Fan-Yong Yan,b* Yun-Ying Gao,b Lei Guob and Zi Kongb

aSchool of Materials Science and Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China, and bSchool of Materials and Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China
*Correspondence e-mail: yfany@yahoo.com

(Received 16 November 2010; accepted 3 December 2010; online 11 December 2010)

In the title compound, C15H14Cl2F3NO, synthesized by the reaction of 3-[(E)-2-chloro-3,3,3-trifluoro­prop-1-en­yl]-2,2-dimethyl­cyclo­propane­carb­oxy­lic acid and 2-chloro­aniline, the aromatic ring makes a dihedral angle of 76.7 (3)° with the plane of the cyclo­propane ring. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into chains running along the b axis.

Related literature

The title compound is an inter­mediate for tefluthrinn (2,3,5,6-tetrafluoro-4-methylbenzyl(1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylate), an insecticide controlling a wide range of soil insect pests, see: Punja (1981[Punja, N. (1981). Eur. Patent EP 0031199.]). For the preparation of the title compound, see Liu & Yan (2007[Liu, D.-Q. & Yan, F.-Y. (2007). Acta Cryst. E63, o4202.]). For a related structure, see: Yan et al. (2010[Yan, F.-Y., Liu, D.-Q., Wen, J.-Y., Gao, Y.-Y. & Li, A.-M. (2011). Acta Cryst. E67, o60.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14Cl2F3NO

  • Mr = 352.17

  • Orthorhombic, P b c a

  • a = 18.454 (4) Å

  • b = 9.3350 (19) Å

  • c = 18.981 (4) Å

  • V = 3269.7 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 113 K

  • 0.40 × 0.06 × 0.06 mm
Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.848, Tmax = 0.975

  • 28276 measured reflections

  • 3873 independent reflections

  • 3325 reflections with I > 2σ(I)

  • Rint = 0.045
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.115

  • S = 1.08

  • 3873 reflections

  • 206 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.81 (2) 2.26 (2) 3.0415 (19) 162 (2)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050634/bt5407sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050634/bt5407Isup2.hkl

checkCIF report


Comment top

3-((E)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate for tefluthrin, an important insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). The title compound may show some insecticide activity. The present X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound. The dihedral angle between the aromatic ring and the cyclopropane groug is 76.7 (3)°. An N-H···O hydrogen bond links the molecules to chains running along the b-axis.

Related literature top

The title compound is an intermediate for tefluthrin, an insecticide controlling a wide range of soil insect pests, see: Punja (1981). For the preparation of the title compound, see Liu & Yan (2007). For a related structure, see: Yan et al. (2011).

Experimental top

The title compound was prepared according to the method of Liu & Yan (2007). The product was recrystallized from methanol and ethyl acetate (5:1) over 5 d at ambient temperature, gave colourless single crystals of (E)-3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-N-(2-chlorophenyl)-2,2- dimethylcyclopropanecarboxamide, suitable for X-ray analysis.

Refinement top

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 amiino H atom was located from a difference map and freely refined.

Structure description top

3-((E)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate for tefluthrin, an important insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). The title compound may show some insecticide activity. The present X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound. The dihedral angle between the aromatic ring and the cyclopropane groug is 76.7 (3)°. An N-H···O hydrogen bond links the molecules to chains running along the b-axis.

The title compound is an intermediate for tefluthrin, an insecticide controlling a wide range of soil insect pests, see: Punja (1981). For the preparation of the title compound, see Liu & Yan (2007). For a related structure, see: Yan et al. (2011).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids. H atoms are drawn as spheres of arbitrary radius.
3-[(E)-2-Chloro-3,3,3-trifluoroprop-1-en-1-yl]-N-(2- chlorophenyl)-2,2-dimethylcyclopropane-1-carboxamide top
Crystal data top
C15H14Cl2F3NODx = 1.431 Mg m−3
Mr = 352.17Melting point: 124 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 18.454 (4) ÅCell parameters from 8396 reflections
b = 9.3350 (19) Åθ = 2.2–27.2°
c = 18.981 (4) ŵ = 0.43 mm−1
V = 3269.7 (11) Å3T = 113 K
Z = 8Block, colorless
F(000) = 14400.40 × 0.06 × 0.06 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3873 independent reflections
Radiation source: rotating anode3325 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.045
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.2°
ω and φ scansh = −22→24
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		k = −10→12
Tmin = 0.848, Tmax = 0.975l = −24→24
28276 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0648P)2 + 0.6506P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3873 reflectionsΔρmax = 0.25 e Å−3
206 parametersΔρmin = −0.37 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0143 (13)
Crystal data top
C15H14Cl2F3NOV = 3269.7 (11) Å3
Mr = 352.17Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 18.454 (4) ŵ = 0.43 mm−1
b = 9.3350 (19) ÅT = 113 K
c = 18.981 (4) Å0.40 × 0.06 × 0.06 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3873 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		3325 reflections with I > 2σ(I)
Tmin = 0.848, Tmax = 0.975Rint = 0.045
28276 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.25 e Å−3
3873 reflectionsΔρmin = −0.37 e Å−3
206 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
xyzUiso*/Ueq
Cl10.15849 (2)0.37167 (5)0.05290 (2)0.03411 (15)
Cl20.44326 (2)0.57979 (5)0.35812 (2)0.03963 (16)
F10.08112 (7)0.08899 (12)0.07614 (7)0.0458 (3)
F20.19548 (7)0.06413 (12)0.09253 (7)0.0490 (3)
F30.12256 (7)0.05370 (11)0.18026 (6)0.0440 (3)
O10.20892 (6)0.32062 (12)0.32957 (6)0.0293 (3)
N10.28640 (7)0.50060 (15)0.35929 (7)0.0237 (3)
C10.13526 (10)0.12238 (19)0.12027 (10)0.0320 (4)
C20.14360 (8)0.27922 (17)0.13093 (8)0.0251 (3)
C30.14182 (9)0.34166 (18)0.19383 (9)0.0275 (3)
H30.13250.28380.23270.033*
C40.15340 (10)0.49437 (18)0.20662 (9)0.0313 (4)
H40.15980.55170.16380.038*
C50.19808 (9)0.54696 (17)0.27041 (9)0.0281 (4)
H50.22780.63180.26110.034*
C60.11674 (10)0.57294 (18)0.26648 (10)0.0346 (4)
C70.06647 (10)0.4966 (2)0.31580 (12)0.0456 (5)
H7A0.01980.48620.29400.068*
H7B0.06160.55100.35850.068*
H7C0.08580.40370.32660.068*
C80.09538 (13)0.7269 (2)0.24999 (14)0.0590 (7)
H8A0.04910.72790.22690.089*
H8B0.13110.76920.21970.089*
H8C0.09250.78070.29300.089*
C90.23019 (8)0.44437 (16)0.32159 (8)0.0232 (3)
C100.33010 (8)0.42237 (17)0.40673 (8)0.0236 (3)
C110.30110 (10)0.31756 (19)0.45095 (9)0.0316 (4)
H110.25150.30010.45050.038*
C120.34543 (11)0.2394 (2)0.49541 (11)0.0416 (5)
H120.32530.16990.52460.050*
C130.41935 (11)0.2637 (2)0.49691 (11)0.0418 (5)
H130.44890.20920.52620.050*
C140.44927 (10)0.3692 (2)0.45467 (10)0.0342 (4)
H140.49880.38720.45600.041*
C150.40456 (9)0.44771 (17)0.41045 (8)0.0269 (3)
H10.2974 (11)0.583 (2)0.3510 (11)0.032 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0350 (2)0.0409 (3)0.0265 (2)−0.00101 (17)0.00151 (16)0.00143 (16)
Cl20.0316 (2)0.0479 (3)0.0394 (3)−0.01434 (18)0.00113 (18)0.0092 (2)
F10.0431 (7)0.0421 (6)0.0521 (7)−0.0071 (5)−0.0118 (5)−0.0169 (5)
F20.0400 (6)0.0392 (7)0.0680 (8)0.0103 (5)0.0079 (6)−0.0207 (6)
F30.0638 (8)0.0226 (5)0.0454 (6)−0.0048 (5)0.0009 (6)−0.0010 (5)
O10.0333 (6)0.0187 (6)0.0361 (6)−0.0026 (4)−0.0067 (5)0.0029 (5)
N10.0257 (7)0.0187 (7)0.0266 (7)−0.0020 (5)−0.0024 (5)0.0029 (5)
C10.0296 (9)0.0295 (9)0.0369 (9)0.0017 (7)−0.0015 (7)−0.0092 (7)
C20.0225 (7)0.0246 (8)0.0281 (7)0.0002 (6)−0.0006 (6)0.0002 (6)
C30.0323 (8)0.0223 (8)0.0279 (8)0.0016 (6)−0.0043 (6)0.0002 (6)
C40.0443 (10)0.0204 (8)0.0292 (8)−0.0010 (7)−0.0113 (7)−0.0002 (6)
C50.0339 (9)0.0186 (7)0.0318 (8)−0.0012 (6)−0.0089 (7)0.0004 (6)
C60.0380 (10)0.0258 (9)0.0401 (10)0.0094 (7)−0.0186 (8)−0.0117 (7)
C70.0307 (9)0.0539 (13)0.0521 (12)0.0106 (9)−0.0046 (8)−0.0234 (10)
C80.0721 (15)0.0283 (10)0.0766 (16)0.0212 (10)−0.0477 (13)−0.0202 (10)
C90.0243 (7)0.0195 (7)0.0257 (7)0.0034 (6)−0.0004 (6)−0.0026 (6)
C100.0232 (8)0.0250 (8)0.0225 (7)0.0012 (6)−0.0010 (6)−0.0002 (6)
C110.0300 (8)0.0332 (9)0.0316 (8)−0.0042 (7)−0.0022 (7)0.0078 (7)
C120.0437 (11)0.0382 (11)0.0429 (10)−0.0058 (8)−0.0092 (8)0.0168 (8)
C130.0429 (10)0.0370 (10)0.0454 (10)0.0061 (8)−0.0147 (9)0.0081 (8)
C140.0251 (8)0.0380 (10)0.0394 (9)0.0038 (7)−0.0053 (7)−0.0040 (8)
C150.0273 (8)0.0263 (8)0.0270 (8)−0.0014 (6)0.0014 (6)−0.0015 (6)
Geometric parameters (Å, º) top
Cl1—C21.7360 (17)C6—C71.498 (3)
Cl2—C151.7368 (17)C6—C81.523 (3)
F1—C11.340 (2)C7—H7A0.9600
F2—C11.345 (2)C7—H7B0.9600
F3—C11.328 (2)C7—H7C0.9600
O1—C91.2294 (19)C8—H8A0.9600
N1—C91.365 (2)C8—H8B0.9600
N1—C101.412 (2)C8—H8C0.9600
N1—H10.81 (2)C10—C111.396 (2)
C1—C21.486 (2)C10—C151.396 (2)
C2—C31.329 (2)C11—C121.383 (3)
C3—C41.462 (2)C11—H110.9300
C3—H30.9300C12—C131.383 (3)
C4—C61.512 (3)C12—H120.9300
C4—C51.545 (2)C13—C141.385 (3)
C4—H40.9800C13—H130.9300
C5—C91.487 (2)C14—C151.387 (2)
C5—C61.522 (2)C14—H140.9300
C5—H50.9800
C9—N1—C10124.70 (14)C6—C7—H7A109.5
C9—N1—H1117.0 (15)C6—C7—H7B109.5
C10—N1—H1118.1 (15)H7A—C7—H7B109.5
F3—C1—F1106.98 (15)C6—C7—H7C109.5
F3—C1—F2106.64 (15)H7A—C7—H7C109.5
F1—C1—F2106.10 (14)H7B—C7—H7C109.5
F3—C1—C2112.16 (14)C6—C8—H8A109.5
F1—C1—C2113.04 (15)C6—C8—H8B109.5
F2—C1—C2111.48 (15)H8A—C8—H8B109.5
C3—C2—C1123.50 (16)C6—C8—H8C109.5
C3—C2—Cl1123.52 (13)H8A—C8—H8C109.5
C1—C2—Cl1112.95 (12)H8B—C8—H8C109.5
C2—C3—C4124.99 (16)O1—C9—N1122.64 (14)
C2—C3—H3117.5O1—C9—C5123.94 (14)
C4—C3—H3117.5N1—C9—C5113.42 (13)
C3—C4—C6122.17 (16)C11—C10—C15117.76 (15)
C3—C4—C5121.21 (14)C11—C10—N1121.81 (15)
C6—C4—C559.72 (11)C15—C10—N1120.43 (14)
C3—C4—H4114.3C12—C11—C10120.65 (16)
C6—C4—H4114.3C12—C11—H11119.7
C5—C4—H4114.3C10—C11—H11119.7
C9—C5—C6121.83 (15)C13—C12—C11120.64 (18)
C9—C5—C4121.32 (14)C13—C12—H12119.7
C6—C5—C459.07 (11)C11—C12—H12119.7
C9—C5—H5114.5C12—C13—C14119.84 (17)
C6—C5—H5114.5C12—C13—H13120.1
C4—C5—H5114.5C14—C13—H13120.1
C7—C6—C4121.05 (15)C13—C14—C15119.29 (17)
C7—C6—C5120.27 (15)C13—C14—H14120.4
C4—C6—C561.21 (11)C15—C14—H14120.4
C7—C6—C8114.65 (18)C14—C15—C10121.78 (16)
C4—C6—C8114.78 (18)C14—C15—Cl2118.48 (13)
C5—C6—C8114.56 (17)C10—C15—Cl2119.74 (13)
F3—C1—C2—C32.9 (2)C9—C5—C6—C8144.09 (17)
F1—C1—C2—C3123.98 (18)C4—C5—C6—C8−105.95 (19)
F2—C1—C2—C3−116.59 (19)C10—N1—C9—O15.5 (2)
F3—C1—C2—Cl1−178.82 (11)C10—N1—C9—C5−174.29 (14)
F1—C1—C2—Cl1−57.75 (18)C6—C5—C9—O150.0 (2)
F2—C1—C2—Cl161.67 (17)C4—C5—C9—O1−20.8 (2)
C1—C2—C3—C4176.79 (16)C6—C5—C9—N1−130.28 (15)
Cl1—C2—C3—C4−1.3 (2)C4—C5—C9—N1159.01 (15)
C2—C3—C4—C6148.84 (17)C9—N1—C10—C11−38.7 (2)
C2—C3—C4—C5−139.55 (18)C9—N1—C10—C15141.04 (16)
C3—C4—C5—C9−0.7 (3)C15—C10—C11—C12−1.7 (3)
C6—C4—C5—C9110.81 (18)N1—C10—C11—C12178.02 (17)
C3—C4—C5—C6−111.54 (19)C10—C11—C12—C130.0 (3)
C3—C4—C6—C70.1 (2)C11—C12—C13—C141.4 (3)
C5—C4—C6—C7−109.91 (18)C12—C13—C14—C15−1.1 (3)
C3—C4—C6—C5109.97 (17)C13—C14—C15—C10−0.7 (3)
C3—C4—C6—C8−144.45 (17)C13—C14—C15—Cl2179.85 (14)
C5—C4—C6—C8105.58 (17)C11—C10—C15—C142.0 (2)
C9—C5—C6—C71.2 (2)N1—C10—C15—C14−177.69 (15)
C4—C5—C6—C7111.14 (18)C11—C10—C15—Cl2−178.50 (13)
C9—C5—C6—C4−109.96 (17)N1—C10—C15—Cl21.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.81 (2)2.26 (2)3.0415 (19)162 (2)
Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC15H14Cl2F3NO
Mr352.17
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)113
a, b, c (Å)18.454 (4), 9.3350 (19), 18.981 (4)
V (Å3)3269.7 (11)
Z8
Radiation typeMo Kα
µ (mm−1)0.43
Crystal size (mm)0.40 × 0.06 × 0.06
Data collection
DiffractometerRigaku Saturn CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.848, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections		28276, 3873, 3325
Rint0.045
(sin θ/λ)max (Å−1)0.657
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.115, 1.08
No. of reflections3873
No. of parameters206
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.25, −0.37

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.81 (2)2.26 (2)3.0415 (19)162 (2)
Symmetry code: (i) −x+1/2, y+1/2, z.
 

Acknowledgements

This work was supported by the National Natural Science Foundation (No. 20376059) and Tianjin Polytechnic University

References

First citationLiu, D.-Q. & Yan, F.-Y. (2007). Acta Cryst. E63, o4202.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o61
https://doi.org/10.1107/S1600536810050634
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