(E)-3-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-2,2-dimethyl-N-p-tolyl­cyclo­propane­carboxamide

Yan, F.-Y.; Liu, D.-Q.

doi:10.1107/S160053680706816X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o451

doi:10.1107/S160053680706816X

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(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-p-tolylcyclopropanecarboxamide

Fan-Yong Yan ^a ^* and Dong-Qing Liu ^a

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

(Received 28 October 2007; accepted 21 December 2007; online 16 January 2008)

There are two molecules in the asymmetric unit of the title compound, C₁₆H₁₇ClF₃NO. The benzene ring in each molecule makes a dihedral angle of 66.6 (3)° [116.3 (4)° in the second molecule] with the plane of the cyclopropane ring. The F atoms of the CF₃ groups are disordered equally over two positions. The amide hydrogen is linked with the amide oxygen in another molecule by an intermolecular N—H⋯O hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Liu et al. (2006 ); Punja (1981 ); Zhang (2005 ).

Experimental

Crystal data

C₁₆H₁₇ClF₃NO
M_r = 331.76
Triclinic, $[P \overline 1]$
a = 9.400 (2) Å
b = 12.482 (3) Å
c = 16.201 (4) Å
α = 70.910 (4)°
β = 88.921 (5)°
γ = 72.517 (4)°
V = 1706.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 294 (2) K
0.22 × 0.18 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick,1996 ) T_min = 0.945, T_max = 0.967
8849 measured reflections
5945 independent reflections
3077 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.207
S = 1.09
5945 reflections
457 parameters
137 restraints
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.15	2.978 (4)	161
N2—H2⋯O1	0.86	2.14	2.959 (4)	158
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706816X/bv2081sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680706816X/bv2081Isup2.hkl

checkCIF report

Comment top

3-[(E)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic 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). p-Toluidine containing pesticides have the advantage of low toxicity, high activity and low residues (Zhang 2005). The structure in this article containing both of two active parts is expected to 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, (I). In this paper, the title compound, (E)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-p-tolylcyclopropane-carboxamide, (I), was synthesized and the structure of (I) is illustrated in Fig. 1. The dihedral angles between the benzene moiety and the cyclopropane group is 66.6 (3)°. The amide hydrogen is linked with the amide oxygen in an adjoining molecule by an intermolecular N—H···O hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N—H···O hydrogen bonds (Table 1).

Related literature top

For related literature, see: Liu et al. (2006); Punja (1981); Zhang (2005).

Experimental top

The title compound was prepared according to the method of Liu et al. (2006). 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 in. The mixture was heated to reflux for 1 h. SOCl₂ was removed by a rotoevaporator. The crude the product could be directly disolved in anhydrous toluene, already mixed with p-toluidine(0.44 g, 4.1 mmol). Triethylamine was dropped into the system, preventing the release of white fumes. After 5 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 (80:1) overnight at ambient temperature gave colorless single crystals of (E)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl -N-p-tolylcyclopropanecarboxamide, suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	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

(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl- N-p-tolylcyclopropanecarboxamide top

Crystal data top

C₁₆H₁₇ClF₃NO	Z = 4
M_r = 331.76	F(000) = 688
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.400 (2) Å	Cell parameters from 2183 reflections
b = 12.482 (3) Å	θ = 2.6–22.9°
c = 16.201 (4) Å	µ = 0.25 mm⁻¹
α = 70.910 (4)°	T = 294 K
β = 88.921 (5)°	Prism, colorless
γ = 72.517 (4)°	0.22 × 0.18 × 0.14 mm
V = 1706.7 (7) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5945 independent reflections
Radiation source: fine-focus sealed tube	3077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −11→9
T_min = 0.945, T_max = 0.967	k = −14→14
8849 measured reflections	l = −19→16

Refinement top

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.207	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0879P)² + 0.5066P] where P = (F_o² + 2F_c²)/3
5945 reflections	(Δ/σ)_max = 0.001
457 parameters	Δρ_max = 0.60 e Å⁻³
137 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₆H₁₇ClF₃NO	γ = 72.517 (4)°
M_r = 331.76	V = 1706.7 (7) Å³
Triclinic, P1	Z = 4
a = 9.400 (2) Å	Mo Kα radiation
b = 12.482 (3) Å	µ = 0.25 mm⁻¹
c = 16.201 (4) Å	T = 294 K
α = 70.910 (4)°	0.22 × 0.18 × 0.14 mm
β = 88.921 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5945 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	3077 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.967	R_int = 0.023
8849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	137 restraints
wR(F²) = 0.207	H-atom parameters constrained
S = 1.09	Δρ_max = 0.60 e Å⁻³
5945 reflections	Δρ_min = −0.45 e Å⁻³
457 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.63184 (16)	0.55693 (11)	1.02621 (11)	0.1052 (5)
Cl2	1.13400 (19)	0.54200 (14)	0.72738 (18)	0.1836 (12)
F1	0.9100 (9)	0.6078 (8)	1.0169 (8)	0.133 (3)	0.50
F2	0.7921 (10)	0.6990 (8)	1.0952 (5)	0.116 (3)	0.50
F3	0.8242 (11)	0.7991 (7)	0.9530 (5)	0.089 (3)	0.50
F1'	0.9073 (7)	0.6378 (7)	0.9589 (6)	0.113 (2)	0.50
F2'	0.8042 (12)	0.8127 (7)	0.9874 (6)	0.095 (3)	0.50
F3'	0.8598 (11)	0.6504 (9)	1.0803 (6)	0.127 (3)	0.50
F4	1.3243 (9)	0.7790 (8)	0.6310 (6)	0.096 (2)	0.50
F5	1.3304 (11)	0.6367 (10)	0.5804 (6)	0.146 (3)	0.50
F6	1.4122 (11)	0.5960 (9)	0.7020 (7)	0.147 (4)	0.50
F4'	1.3120 (12)	0.7716 (9)	0.5891 (6)	0.118 (3)	0.50
F5'	1.3672 (10)	0.5822 (7)	0.6257 (7)	0.127 (3)	0.50
F6'	1.4006 (8)	0.6447 (7)	0.7274 (5)	0.109 (2)	0.50
O1	0.4629 (3)	1.0115 (3)	0.78523 (18)	0.0712 (8)
O2	0.9714 (3)	0.9971 (3)	0.70315 (19)	0.0708 (8)
N1	0.2560 (3)	1.0571 (3)	0.6969 (2)	0.0580 (8)
H1	0.1829	1.0320	0.6898	0.070*
N2	0.7591 (3)	1.0502 (3)	0.7686 (2)	0.0586 (9)
H2	0.6831	1.0277	0.7877	0.070*
C1	0.7972 (6)	0.7010 (5)	1.0040 (4)	0.106 (2)
C2	0.6514 (4)	0.6955 (4)	0.9814 (3)	0.0653 (11)
C3	0.5468 (4)	0.7882 (4)	0.9324 (3)	0.0692 (12)
H3	0.5683	0.8601	0.9133	0.083*
C4	0.3983 (4)	0.7911 (4)	0.9041 (3)	0.0726 (13)
H4	0.3870	0.7123	0.9147	0.087*
C5	0.3031 (4)	0.8882 (4)	0.8247 (3)	0.0665 (12)
H5	0.2412	0.8608	0.7933	0.080*
C6	0.2592 (5)	0.8832 (5)	0.9160 (3)	0.0831 (15)
C7	0.2734 (6)	0.9764 (6)	0.9514 (4)	0.112 (2)
H7A	0.1832	1.0430	0.9346	0.168*
H7B	0.3566	1.0025	0.9281	0.168*
H7C	0.2895	0.9436	1.0142	0.168*
C8	0.1253 (5)	0.8399 (6)	0.9429 (4)	0.136 (3)
H8A	0.1212	0.8201	1.0052	0.203*
H8B	0.1348	0.7706	0.9271	0.203*
H8C	0.0352	0.9018	0.9136	0.203*
C9	0.3514 (4)	0.9896 (3)	0.7677 (3)	0.0540 (10)
C10	0.2592 (4)	1.1642 (4)	0.6323 (3)	0.0581 (10)
C11	0.3843 (5)	1.2017 (4)	0.6188 (3)	0.0752 (13)
H11	0.4731	1.1556	0.6538	0.090*
C12	0.3780 (6)	1.3067 (5)	0.5542 (3)	0.0825 (14)
H12	0.4633	1.3308	0.5469	0.099*
C13	0.2518 (6)	1.3772 (4)	0.5000 (3)	0.0809 (14)
C14	0.1285 (6)	1.3385 (5)	0.5130 (3)	0.0926 (16)
H14	0.0407	1.3846	0.4771	0.111*
C15	0.1306 (5)	1.2333 (4)	0.5776 (3)	0.0738 (12)
H15	0.0455	1.2090	0.5842	0.089*
C16	0.2484 (7)	1.4916 (5)	0.4283 (4)	0.126 (2)
H16A	0.2562	1.5491	0.4540	0.190*
H16B	0.1560	1.5224	0.3919	0.190*
H16C	0.3309	1.4762	0.3935	0.190*
C17	1.3029 (6)	0.6758 (5)	0.6514 (4)	0.1067 (19)
C18	1.1515 (5)	0.6795 (4)	0.6771 (3)	0.0761 (13)
C19	1.0418 (4)	0.7782 (4)	0.6611 (3)	0.0705 (12)
H19	1.0622	0.8486	0.6311	0.085*
C20	0.8898 (4)	0.7886 (4)	0.6857 (3)	0.0694 (12)
H20	0.8712	0.7119	0.7122	0.083*
C21	0.7992 (4)	0.8857 (4)	0.7199 (3)	0.0606 (11)
H21	0.7331	0.8598	0.7643	0.073*
C22	0.7560 (4)	0.8877 (4)	0.6299 (3)	0.0690 (12)
C23	0.7770 (5)	0.9826 (4)	0.5517 (3)	0.0881 (15)
H23A	0.8666	0.9997	0.5623	0.132*
H23B	0.6926	1.0533	0.5404	0.132*
H23C	0.7854	0.9562	0.5019	0.132*
C24	0.6168 (5)	0.8525 (5)	0.6222 (4)	0.1013 (18)
H24A	0.5301	0.9220	0.6081	0.152*
H24B	0.6078	0.7954	0.6769	0.152*
H24C	0.6247	0.8180	0.5767	0.152*
C25	0.8538 (4)	0.9809 (4)	0.7301 (3)	0.0549 (10)
C26	0.7657 (4)	1.1539 (4)	0.7823 (2)	0.0551 (10)
C27	0.8957 (4)	1.1829 (4)	0.7839 (3)	0.0685 (12)
H27	0.9858	1.1327	0.7751	0.082*
C28	0.8923 (5)	1.2861 (4)	0.7986 (3)	0.0714 (12)
H28	0.9812	1.3041	0.7995	0.086*
C29	0.7633 (5)	1.3630 (4)	0.8118 (3)	0.0742 (12)
C30	0.6350 (5)	1.3321 (4)	0.8109 (3)	0.0843 (14)
H30	0.5453	1.3822	0.8202	0.101*
C31	0.6353 (5)	1.2295 (4)	0.7966 (3)	0.0751 (13)
H31	0.5465	1.2111	0.7966	0.090*
C32	0.7605 (6)	1.4761 (5)	0.8269 (4)	0.1064 (18)
H32A	0.8376	1.4586	0.8718	0.160*
H32B	0.6647	1.5105	0.8450	0.160*
H32C	0.7776	1.5316	0.7736	0.160*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1007 (10)	0.0663 (8)	0.1359 (13)	−0.0321 (7)	−0.0128 (8)	−0.0109 (8)
Cl2	0.0972 (12)	0.0787 (10)	0.283 (3)	−0.0084 (9)	0.0387 (14)	0.0387 (13)
F1	0.095 (4)	0.144 (5)	0.139 (5)	−0.027 (4)	−0.006 (4)	−0.025 (4)
F2	0.107 (5)	0.117 (5)	0.119 (4)	−0.040 (4)	−0.039 (3)	−0.025 (3)
F3	0.067 (4)	0.104 (4)	0.099 (5)	−0.049 (3)	−0.002 (3)	−0.019 (3)
F1'	0.067 (3)	0.124 (4)	0.131 (5)	−0.021 (3)	0.011 (3)	−0.030 (4)
F2'	0.084 (4)	0.106 (4)	0.109 (5)	−0.053 (3)	−0.003 (4)	−0.032 (3)
F3'	0.108 (5)	0.136 (5)	0.128 (5)	−0.040 (4)	−0.033 (4)	−0.028 (4)
F4	0.064 (3)	0.113 (4)	0.111 (5)	−0.043 (3)	0.025 (4)	−0.023 (4)
F5	0.124 (5)	0.161 (5)	0.146 (5)	−0.039 (4)	0.049 (4)	−0.048 (4)
F6	0.113 (5)	0.147 (5)	0.159 (5)	−0.014 (4)	0.007 (4)	−0.046 (4)
F4'	0.091 (4)	0.126 (5)	0.117 (5)	−0.038 (3)	0.034 (4)	−0.013 (4)
F5'	0.104 (4)	0.125 (5)	0.133 (5)	−0.018 (3)	0.033 (4)	−0.038 (4)
F6'	0.058 (3)	0.120 (4)	0.139 (5)	−0.014 (3)	−0.016 (3)	−0.042 (4)
O1	0.0452 (15)	0.090 (2)	0.0752 (19)	−0.0406 (14)	−0.0030 (13)	−0.0050 (16)
O2	0.0466 (15)	0.095 (2)	0.091 (2)	−0.0404 (15)	0.0181 (14)	−0.0415 (18)
N1	0.0428 (17)	0.073 (2)	0.059 (2)	−0.0291 (16)	0.0015 (15)	−0.0140 (18)
N2	0.0421 (18)	0.072 (2)	0.068 (2)	−0.0311 (16)	0.0106 (15)	−0.0206 (18)
C1	0.071 (4)	0.086 (4)	0.134 (6)	−0.019 (3)	−0.020 (4)	−0.004 (4)
C2	0.051 (2)	0.069 (3)	0.074 (3)	−0.028 (2)	−0.001 (2)	−0.013 (2)
C3	0.049 (2)	0.069 (3)	0.082 (3)	−0.031 (2)	−0.004 (2)	−0.004 (2)
C4	0.052 (2)	0.069 (3)	0.088 (3)	−0.034 (2)	−0.007 (2)	−0.001 (2)
C5	0.047 (2)	0.082 (3)	0.069 (3)	−0.036 (2)	−0.0034 (19)	−0.008 (2)
C6	0.047 (2)	0.108 (4)	0.068 (3)	−0.029 (2)	0.008 (2)	0.009 (3)
C7	0.097 (4)	0.136 (5)	0.077 (4)	−0.008 (4)	0.016 (3)	−0.028 (4)
C8	0.055 (3)	0.173 (6)	0.116 (5)	−0.047 (3)	0.009 (3)	0.043 (4)
C9	0.038 (2)	0.071 (3)	0.054 (2)	−0.0223 (19)	0.0057 (17)	−0.017 (2)
C10	0.050 (2)	0.075 (3)	0.053 (2)	−0.023 (2)	0.0093 (18)	−0.022 (2)
C11	0.063 (3)	0.090 (3)	0.068 (3)	−0.039 (2)	0.004 (2)	−0.008 (3)
C12	0.084 (3)	0.096 (4)	0.066 (3)	−0.047 (3)	0.015 (3)	−0.009 (3)
C13	0.085 (3)	0.078 (3)	0.066 (3)	−0.021 (3)	0.025 (3)	−0.011 (3)
C14	0.068 (3)	0.093 (4)	0.079 (4)	0.003 (3)	0.008 (3)	−0.007 (3)
C15	0.050 (2)	0.084 (3)	0.073 (3)	−0.016 (2)	0.004 (2)	−0.013 (3)
C16	0.124 (5)	0.099 (4)	0.103 (5)	−0.014 (4)	0.032 (4)	0.015 (4)
C17	0.066 (4)	0.095 (5)	0.127 (6)	−0.004 (3)	0.002 (3)	−0.015 (4)
C18	0.049 (3)	0.071 (3)	0.087 (3)	−0.015 (2)	0.002 (2)	−0.002 (2)
C19	0.047 (2)	0.066 (3)	0.094 (3)	−0.022 (2)	0.007 (2)	−0.017 (2)
C20	0.051 (2)	0.060 (3)	0.098 (3)	−0.026 (2)	0.011 (2)	−0.021 (2)
C21	0.042 (2)	0.069 (3)	0.076 (3)	−0.0286 (19)	0.0094 (19)	−0.022 (2)
C22	0.044 (2)	0.073 (3)	0.098 (4)	−0.016 (2)	−0.006 (2)	−0.040 (3)
C23	0.084 (3)	0.092 (4)	0.082 (4)	−0.016 (3)	−0.014 (3)	−0.031 (3)
C24	0.054 (3)	0.122 (4)	0.156 (5)	−0.029 (3)	−0.004 (3)	−0.081 (4)
C25	0.037 (2)	0.070 (3)	0.057 (2)	−0.0222 (19)	−0.0018 (17)	−0.014 (2)
C26	0.045 (2)	0.066 (3)	0.053 (2)	−0.0225 (19)	0.0024 (17)	−0.014 (2)
C27	0.051 (2)	0.090 (3)	0.077 (3)	−0.031 (2)	0.008 (2)	−0.035 (3)
C28	0.061 (3)	0.088 (3)	0.075 (3)	−0.035 (3)	0.003 (2)	−0.030 (3)
C29	0.077 (3)	0.075 (3)	0.069 (3)	−0.028 (3)	−0.006 (2)	−0.017 (2)
C30	0.066 (3)	0.079 (3)	0.102 (4)	−0.014 (3)	0.002 (3)	−0.032 (3)
C31	0.052 (3)	0.085 (3)	0.091 (3)	−0.026 (2)	0.009 (2)	−0.029 (3)
C32	0.106 (4)	0.091 (4)	0.132 (5)	−0.030 (3)	−0.003 (3)	−0.049 (4)

Geometric parameters (Å, º) top

Cl1—C2	1.708 (4)	C11—H11	0.9300
Cl2—C18	1.699 (5)	C12—C13	1.363 (7)
F1—C1	1.276 (8)	C12—H12	0.9300
F2—C1	1.468 (8)	C13—C14	1.372 (7)
F3—C1	1.328 (8)	C13—C16	1.510 (7)
F1'—C1	1.444 (8)	C14—C15	1.380 (6)
F2'—C1	1.352 (8)	C14—H14	0.9300
F3'—C1	1.251 (8)	C15—H15	0.9300
F4—C17	1.297 (10)	C16—H16A	0.9600
F5—C17	1.382 (8)	C16—H16B	0.9600
F6—C17	1.265 (8)	C16—H16C	0.9600
F4'—C17	1.313 (8)	C17—C18	1.467 (7)
F5'—C17	1.338 (8)	C18—C19	1.298 (6)
F6'—C17	1.423 (8)	C19—C20	1.456 (5)
O1—C9	1.219 (4)	C19—H19	0.9300
O2—C25	1.230 (4)	C20—C21	1.517 (6)
N1—C9	1.335 (5)	C20—C22	1.519 (6)
N1—C10	1.411 (5)	C20—H20	0.9800
N1—H1	0.8600	C21—C25	1.484 (5)
N2—C25	1.341 (5)	C21—C22	1.511 (6)
N2—C26	1.403 (5)	C21—H21	0.9800
N2—H2	0.8600	C22—C23	1.481 (7)
C1—C2	1.453 (6)	C22—C24	1.519 (6)
C2—C3	1.297 (5)	C23—H23A	0.9600
C3—C4	1.464 (5)	C23—H23B	0.9600
C3—H3	0.9300	C23—H23C	0.9600
C4—C5	1.515 (6)	C24—H24A	0.9600
C4—C6	1.516 (7)	C24—H24B	0.9600
C4—H4	0.9800	C24—H24C	0.9600
C5—C9	1.492 (5)	C26—C31	1.372 (6)
C5—C6	1.514 (7)	C26—C27	1.377 (5)
C5—H5	0.9800	C27—C28	1.376 (6)
C6—C7	1.495 (8)	C27—H27	0.9300
C6—C8	1.516 (6)	C28—C29	1.365 (6)
C7—H7A	0.9600	C28—H28	0.9300
C7—H7B	0.9600	C29—C30	1.374 (6)
C7—H7C	0.9600	C29—C32	1.502 (7)
C8—H8A	0.9600	C30—C31	1.374 (6)
C8—H8B	0.9600	C30—H30	0.9300
C8—H8C	0.9600	C31—H31	0.9300
C10—C15	1.380 (6)	C32—H32A	0.9600
C10—C11	1.380 (5)	C32—H32B	0.9600
C11—C12	1.369 (6)	C32—H32C	0.9600

C9—N1—C10	128.6 (3)	F4—C17—F4'	32.5 (6)
C9—N1—H1	115.7	F6—C17—F5'	64.6 (7)
C10—N1—H1	115.7	F4—C17—F5'	130.9 (7)
C25—N2—C26	129.5 (3)	F4'—C17—F5'	107.5 (8)
C25—N2—H2	115.2	F6—C17—F5	96.3 (8)
C26—N2—H2	115.2	F4—C17—F5	108.3 (8)
F1—C1—F3	112.4 (7)	F4'—C17—F5	77.7 (7)
F3'—C1—F2'	101.0 (8)	F5'—C17—F5	34.8 (5)
F3'—C1—F1'	99.0 (7)	F6—C17—F6'	35.0 (5)
F2'—C1—F1'	110.7 (7)	F4—C17—F6'	84.8 (7)
F3'—C1—C2	121.7 (6)	F4'—C17—F6'	112.5 (8)
F1—C1—C2	118.0 (6)	F5'—C17—F6'	99.3 (7)
F3—C1—C2	112.8 (6)	F5—C17—F6'	128.3 (7)
F2'—C1—C2	114.6 (6)	F6—C17—C18	117.7 (7)
F1'—C1—C2	108.6 (5)	F4—C17—C18	112.6 (6)
F3—C1—F2	110.4 (7)	F4'—C17—C18	115.2 (6)
C2—C1—F2	104.4 (5)	F5'—C17—C18	111.8 (6)
C3—C2—C1	122.4 (4)	F5—C17—C18	110.4 (6)
C3—C2—Cl1	124.0 (3)	F6'—C17—C18	109.4 (6)
C1—C2—Cl1	113.6 (3)	C19—C18—C17	123.0 (4)
C2—C3—C4	126.5 (4)	C19—C18—Cl2	123.8 (3)
C2—C3—H3	116.8	C17—C18—Cl2	113.2 (4)
C4—C3—H3	116.8	C18—C19—C20	126.0 (4)
C3—C4—C5	123.0 (3)	C18—C19—H19	117.0
C3—C4—C6	120.3 (4)	C20—C19—H19	117.0
C5—C4—C6	59.9 (3)	C19—C20—C21	123.0 (4)
C3—C4—H4	114.3	C19—C20—C22	121.5 (4)
C5—C4—H4	114.3	C21—C20—C22	59.7 (3)
C6—C4—H4	114.3	C19—C20—H20	114.0
C9—C5—C6	120.5 (4)	C21—C20—H20	114.0
C9—C5—C4	123.5 (3)	C22—C20—H20	114.0
C6—C5—C4	60.1 (3)	C25—C21—C22	120.6 (4)
C9—C5—H5	114.1	C25—C21—C20	124.1 (3)
C6—C5—H5	114.1	C22—C21—C20	60.2 (3)
C4—C5—H5	114.1	C25—C21—H21	113.9
C7—C6—C5	119.8 (4)	C22—C21—H21	113.9
C7—C6—C8	114.9 (5)	C20—C21—H21	113.9
C5—C6—C8	115.3 (5)	C23—C22—C21	118.9 (4)
C7—C6—C4	120.1 (4)	C23—C22—C20	120.8 (4)
C5—C6—C4	60.0 (3)	C21—C22—C20	60.1 (3)
C8—C6—C4	115.8 (5)	C23—C22—C24	114.9 (4)
C6—C7—H7A	109.5	C21—C22—C24	115.6 (4)
C6—C7—H7B	109.5	C20—C22—C24	115.7 (4)
H7A—C7—H7B	109.5	C22—C23—H23A	109.5
C6—C7—H7C	109.5	C22—C23—H23B	109.5
H7A—C7—H7C	109.5	H23A—C23—H23B	109.5
H7B—C7—H7C	109.5	C22—C23—H23C	109.5
C6—C8—H8A	109.5	H23A—C23—H23C	109.5
C6—C8—H8B	109.5	H23B—C23—H23C	109.5
H8A—C8—H8B	109.5	C22—C24—H24A	109.5
C6—C8—H8C	109.5	C22—C24—H24B	109.5
H8A—C8—H8C	109.5	H24A—C24—H24B	109.5
H8B—C8—H8C	109.5	C22—C24—H24C	109.5
O1—C9—N1	123.4 (3)	H24A—C24—H24C	109.5
O1—C9—C5	123.9 (3)	H24B—C24—H24C	109.5
N1—C9—C5	112.7 (3)	O2—C25—N2	123.5 (4)
C15—C10—C11	118.2 (4)	O2—C25—C21	123.3 (4)
C15—C10—N1	117.8 (3)	N2—C25—C21	113.2 (3)
C11—C10—N1	123.9 (4)	C31—C26—C27	118.4 (4)
C12—C11—C10	120.2 (4)	C31—C26—N2	117.8 (3)
C12—C11—H11	119.9	C27—C26—N2	123.8 (4)
C10—C11—H11	119.9	C28—C27—C26	120.0 (4)
C13—C12—C11	122.6 (4)	C28—C27—H27	120.0
C13—C12—H12	118.7	C26—C27—H27	120.0
C11—C12—H12	118.7	C29—C28—C27	122.5 (4)
C12—C13—C14	116.9 (5)	C29—C28—H28	118.8
C12—C13—C16	121.6 (5)	C27—C28—H28	118.8
C14—C13—C16	121.5 (5)	C28—C29—C30	116.8 (4)
C13—C14—C15	122.1 (5)	C28—C29—C32	122.0 (4)
C13—C14—H14	118.9	C30—C29—C32	121.2 (5)
C15—C14—H14	118.9	C31—C30—C29	122.0 (4)
C10—C15—C14	120.0 (4)	C31—C30—H30	119.0
C10—C15—H15	120.0	C29—C30—H30	119.0
C14—C15—H15	120.0	C26—C31—C30	120.4 (4)
C13—C16—H16A	109.5	C26—C31—H31	119.8
C13—C16—H16B	109.5	C30—C31—H31	119.8
H16A—C16—H16B	109.5	C29—C32—H32A	109.5
C13—C16—H16C	109.5	C29—C32—H32B	109.5
H16A—C16—H16C	109.5	H32A—C32—H32B	109.5
H16B—C16—H16C	109.5	C29—C32—H32C	109.5
F6—C17—F4	110.0 (8)	H32A—C32—H32C	109.5
F6—C17—F4'	125.2 (9)	H32B—C32—H32C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.15	2.978 (4)	161
N2—H2···O1	0.86	2.14	2.959 (4)	158

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇ClF₃NO
M_r	331.76
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.400 (2), 12.482 (3), 16.201 (4)
α, β, γ (°)	70.910 (4), 88.921 (5), 72.517 (4)
V (Å³)	1706.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.22 × 0.18 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick,1996)
T_min, T_max	0.945, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	8849, 5945, 3077
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.207, 1.09
No. of reflections	5945
No. of parameters	457
No. of restraints	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.45

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.15	2.978 (4)	161.0
N2—H2···O1	0.86	2.14	2.959 (4)	158.4

Symmetry code: (i) x−1, y, z.

Acknowledgements

This work was supported by the National Natural Science Foundation (No. 20376059)

References

Bruker (1997). SADABS, SMART, and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, D.-Q., Feng, Y.-Q., Liu, D.-W. & Zhang, S.-S. (2006). Acta Cryst. E62, o1747–o1748. Web of Science CSD CrossRef IUCr Journals Google Scholar
Punja, N. (1981). European Patent EP 0 031 199. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Zhang, M. H. (2005). Fine Spec. Chem. 13, 1–4. Google Scholar

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Volume 64| Part 2| February 2008| Page o451

doi:10.1107/S160053680706816X

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

(E)-3-(2-Chloro-3,3,3-tri­fluoro­prop-1-en­yl)-2,2-di­methyl-N-p-tolyl­cyclo­propane­carboxamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-p-tolylcyclopropanecarboxamide