3-(2-Chloro-3,3,3-trifluoro­prop-1-en-1-yl)-2,2-dimethyl-N-[3-(trifluoro­meth­yl)phen­yl]cyclo­propane­carboxamide

Rao, G.-W.; Li, X.-M.; Sun, N.-B.

doi:10.1107/S1600536812020922

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1743

doi:10.1107/S1600536812020922

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3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethyl-N-[3-(trifluoromethyl)phenyl]cyclopropanecarboxamide

Guo-Wu Rao,^a ^* Xiao-Min Li ^a and Na-Bo Sun ^b

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, People's Republic of China, and ^bCollege of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou, 310015, People's Republic of China
^*Correspondence e-mail: rgw@zjut.edu.cn

(Received 8 May 2012; accepted 8 May 2012; online 16 May 2012)

In the title molecule, C₁₆H₁₄ClF₆NO, the cyclopropane ring forms a dihedral angle of 70.82 (18)° with the benzene ring. The torsion angles about the ethylene and amide bonds are −2.2 (5) (Cl—C—C—C) and 0.8 (5)° (O—C—N—C). A supramolecular chain propagated by glide symmetry along [001] and mediated by N—H⋯O hydrogen bonds is observed in the crystal packing.

Related literature

For the biological activity of pyrethroids, see: Chen et al. (1991 ); Sun et al. (2007 , 2008 ). For the synthesis of the title compound, see: Sun et al. (2007).

Experimental

Crystal data

C₁₆H₁₄ClF₆NO
M_r = 385.73
Monoclinic, P 2₁ /c
a = 11.006 (3) Å
b = 16.699 (4) Å
c = 9.659 (2) Å
β = 93.009 (3)°
V = 1772.8 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.60 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.846, T_max = 0.967
7354 measured reflections
3120 independent reflections
2247 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.175
S = 1.04
3120 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.15	2.974 (3)	161
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020922/tk5094sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020922/tk5094Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020922/tk5094Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812020922/tk5094Isup4.cml

checkCIF report

Comment top

Pyrethroids have a high potential for biological activity with low toxicity and good environmental compatibility. These have been widely used in pesticides (Chen et al., 1991; Sun et al., 2007, 2008). In continuation of our studies of biological activities in pyrethroids, we have obtained a colourless crystalline compound, (I). The structure was confirmed by single-crystal X-ray diffraction.

The molecular structure of (I) is illustrated in Fig. 1. In (I), the cyclopropane ring (C4—C6) forms dihedral angles of 89.70 (23) and 70.82 (18)° with the least-squares planes of the (C5,C7,C8) plane and the phenyl ring, respectively. The Cl1—C2—C3—C4 and O1—C9—N1—C10 torsion angles are -2.2 (5) and 0.8 (5)°, respectively. A supramolecular chain propagated by glide symmetry along [001] and mediated by N—H···O hydrogen bonds, Table 1, is observed in the crystal packing.

Related literature top

For the biological activity of pyrethroids, see: Chen et al. (1991); Sun et al. (2007, 2008). For the synthesis of the title compound, see: Sun et al. (2007).

Experimental top

The title compound was synthesized according to the literature procedure (Sun et al., 2007). A solution of the compound in ethanol was concentrated gradually at room temperature to afford colourless blocks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I), shown with 30% probability displacement ellipsoids. The F atoms of the CF₃ group have 50% occupancy factors.

3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethyl- N-[3-(trifluoromethyl)phenyl]cyclopropanecarboxamide top

Crystal data top

C₁₆H₁₄ClF₆NO	Z = 4
M_r = 385.73	F(000) = 784
Monoclinic, P2₁/c	D_x = 1.445 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.006 (3) Å	µ = 0.28 mm⁻¹
b = 16.699 (4) Å	T = 298 K
c = 9.659 (2) Å	Block, colourless
β = 93.009 (3)°	0.60 × 0.13 × 0.12 mm
V = 1772.8 (7) Å³

Data collection top

Bruker SMART CCD diffractometer	3120 independent reflections
Radiation source: fine-focus sealed tube	2247 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→12
T_min = 0.846, T_max = 0.967	k = −19→19
7354 measured reflections	l = −10→11

Refinement top

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)] = 0.064	H-atom parameters constrained
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.0682P)² + 1.1818P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3120 reflections	Δρ_max = 0.52 e Å⁻³
256 parameters	Δρ_min = −0.48 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0120 (19)

Crystal data top

C₁₆H₁₄ClF₆NO	V = 1772.8 (7) Å³
M_r = 385.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.006 (3) Å	µ = 0.28 mm⁻¹
b = 16.699 (4) Å	T = 298 K
c = 9.659 (2) Å	0.60 × 0.13 × 0.12 mm
β = 93.009 (3)°

Data collection top

Bruker SMART CCD diffractometer	3120 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2247 reflections with I > 2σ(I)
T_min = 0.846, T_max = 0.967	R_int = 0.026
7354 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.04	Δρ_max = 0.52 e Å⁻³
3120 reflections	Δρ_min = −0.48 e Å⁻³
256 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)
C1	1.3041 (4)	0.0980 (3)	−0.1232 (4)	0.0913 (12)
C2	1.3072 (3)	0.1266 (2)	0.0223 (3)	0.0685 (9)
C3	1.2130 (3)	0.12532 (19)	0.0995 (3)	0.0630 (8)
H3	1.1393	0.1088	0.0573	0.076*
C4	1.2130 (3)	0.14749 (19)	0.2459 (3)	0.0619 (8)
H4	1.2944	0.1552	0.2899	0.074*
C5	1.1223 (3)	0.1129 (2)	0.3411 (3)	0.0721 (9)
C8	1.1705 (4)	0.0951 (3)	0.4888 (4)	0.1193 (18)
H8B	1.2049	0.0423	0.4928	0.179*
H8A	1.1049	0.0983	0.5503	0.179*
H8C	1.2319	0.1336	0.5162	0.179*
C7	1.0243 (4)	0.0577 (2)	0.2842 (5)	0.0998 (13)
H7A	0.9567	0.0590	0.3432	0.150*
H7B	1.0556	0.0041	0.2805	0.150*
H7C	0.9978	0.0747	0.1926	0.150*
C6	1.1158 (3)	0.20070 (18)	0.3045 (3)	0.0560 (7)
H6	1.1463	0.2363	0.3792	0.067*
C9	1.0126 (2)	0.23407 (16)	0.2185 (2)	0.0476 (6)
C10	0.8386 (3)	0.32746 (16)	0.2473 (3)	0.0527 (7)
C11	0.7832 (3)	0.37131 (19)	0.3483 (3)	0.0663 (8)
H11	0.8163	0.3716	0.4389	0.080*
C12	0.6798 (3)	0.4141 (2)	0.3148 (4)	0.0818 (10)
H12	0.6429	0.4433	0.3831	0.098*
C13	0.6299 (3)	0.4144 (2)	0.1813 (4)	0.0798 (10)
H13	0.5598	0.4437	0.1588	0.096*
C14	0.6848 (3)	0.37073 (18)	0.0813 (4)	0.0665 (8)
C15	0.7895 (3)	0.32759 (18)	0.1131 (3)	0.0608 (8)
H15	0.8267	0.2988	0.0445	0.073*
C16	0.6311 (4)	0.3696 (3)	−0.0649 (5)	0.0911 (12)
Cl1	1.44791 (11)	0.15833 (11)	0.08073 (14)	0.1439 (7)
F1	1.3420 (3)	0.15215 (19)	−0.2109 (3)	0.1418 (12)
F2	1.1945 (3)	0.0778 (2)	−0.1683 (3)	0.1437 (13)
F3	1.3764 (3)	0.03595 (16)	−0.1382 (3)	0.1264 (10)
N1	0.9449 (2)	0.28521 (14)	0.2908 (2)	0.0565 (6)
H1	0.9703	0.2932	0.3754	0.068*
O1	0.98962 (18)	0.21704 (13)	0.09703 (18)	0.0643 (6)
F4	0.5087 (8)	0.3754 (17)	−0.0623 (13)	0.165 (5)	0.50
F5	0.661 (3)	0.4283 (13)	−0.1320 (16)	0.214 (9)	0.50
F6	0.643 (2)	0.3051 (10)	−0.1269 (15)	0.152 (9)	0.50
F4'	0.568 (2)	0.4289 (10)	−0.1007 (11)	0.153 (6)	0.50
F5'	0.7204 (9)	0.3700 (15)	−0.1603 (8)	0.132 (4)	0.50
F6'	0.575 (3)	0.3062 (10)	−0.0982 (18)	0.177 (9)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.094 (3)	0.121 (3)	0.060 (2)	0.026 (3)	0.017 (2)	−0.008 (2)
C2	0.072 (2)	0.083 (2)	0.0508 (18)	0.0154 (17)	0.0072 (15)	0.0018 (15)
C3	0.0602 (18)	0.081 (2)	0.0475 (16)	0.0132 (15)	0.0012 (14)	−0.0018 (14)
C4	0.0577 (17)	0.086 (2)	0.0414 (15)	0.0140 (15)	−0.0021 (12)	0.0013 (14)
C5	0.084 (2)	0.081 (2)	0.0524 (18)	0.0249 (19)	0.0141 (16)	0.0172 (16)
C8	0.149 (4)	0.148 (4)	0.062 (2)	0.073 (3)	0.023 (2)	0.045 (2)
C7	0.111 (3)	0.072 (2)	0.120 (4)	0.003 (2)	0.037 (3)	0.014 (2)
C6	0.0630 (17)	0.0717 (19)	0.0329 (13)	0.0080 (14)	−0.0013 (12)	−0.0027 (12)
C9	0.0560 (15)	0.0559 (15)	0.0308 (13)	−0.0004 (12)	0.0011 (11)	0.0031 (11)
C10	0.0588 (16)	0.0527 (16)	0.0466 (15)	0.0036 (13)	0.0027 (12)	0.0037 (12)
C11	0.071 (2)	0.073 (2)	0.0561 (18)	0.0065 (16)	0.0095 (15)	−0.0040 (15)
C12	0.079 (2)	0.085 (2)	0.082 (3)	0.0180 (19)	0.020 (2)	−0.0061 (19)
C13	0.067 (2)	0.076 (2)	0.097 (3)	0.0186 (17)	0.0053 (19)	0.010 (2)
C14	0.0655 (19)	0.0607 (18)	0.073 (2)	0.0051 (15)	−0.0035 (16)	0.0097 (16)
C15	0.0709 (19)	0.0603 (17)	0.0510 (17)	0.0113 (15)	0.0013 (14)	0.0012 (14)
C16	0.089 (3)	0.093 (3)	0.088 (3)	0.022 (3)	−0.026 (2)	0.014 (3)
Cl1	0.0863 (8)	0.2456 (18)	0.1022 (9)	−0.0409 (9)	0.0265 (6)	−0.0419 (10)
F1	0.192 (3)	0.173 (3)	0.0640 (15)	0.027 (2)	0.0439 (17)	0.0278 (16)
F2	0.109 (2)	0.251 (4)	0.0706 (15)	0.001 (2)	−0.0003 (14)	−0.0609 (19)
F3	0.152 (2)	0.133 (2)	0.0976 (19)	0.0426 (18)	0.0355 (16)	−0.0290 (15)
N1	0.0674 (15)	0.0694 (15)	0.0320 (11)	0.0117 (12)	−0.0038 (10)	−0.0053 (10)
O1	0.0720 (13)	0.0879 (15)	0.0323 (10)	0.0193 (11)	−0.0052 (9)	−0.0060 (9)
F4	0.088 (5)	0.259 (15)	0.142 (8)	0.039 (7)	−0.058 (5)	−0.037 (9)
F5	0.34 (2)	0.183 (14)	0.107 (10)	−0.117 (14)	−0.092 (13)	0.088 (10)
F6	0.200 (14)	0.154 (14)	0.093 (6)	0.098 (13)	−0.076 (9)	−0.054 (9)
F4'	0.188 (13)	0.145 (10)	0.122 (6)	0.105 (11)	−0.031 (9)	0.024 (7)
F5'	0.116 (5)	0.212 (11)	0.068 (3)	0.017 (7)	−0.009 (3)	0.024 (6)
F6'	0.239 (17)	0.142 (13)	0.139 (10)	−0.088 (13)	−0.094 (11)	0.044 (9)

Geometric parameters (Å, º) top

C1—F2	1.305 (5)	C9—O1	1.221 (3)
C1—F3	1.319 (4)	C9—N1	1.351 (3)
C1—F1	1.321 (5)	C10—C15	1.378 (4)
C1—C2	1.483 (5)	C10—C11	1.387 (4)
C2—C3	1.309 (4)	C10—N1	1.411 (3)
C2—Cl1	1.704 (4)	C11—C12	1.367 (5)
C3—C4	1.462 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.376 (5)
C4—C5	1.507 (4)	C12—H12	0.9300
C4—C6	1.522 (4)	C13—C14	1.375 (5)
C4—H4	0.9800	C13—H13	0.9300
C5—C7	1.500 (5)	C14—C15	1.380 (4)
C5—C6	1.509 (4)	C14—C16	1.502 (5)
C5—C8	1.525 (5)	C15—H15	0.9300
C8—H8B	0.9600	C16—F5	1.230 (10)
C8—H8A	0.9600	C16—F6	1.242 (11)
C8—H8C	0.9600	C16—F4'	1.246 (9)
C7—H7A	0.9600	C16—F6'	1.258 (12)
C7—H7B	0.9600	C16—F4	1.352 (10)
C7—H7C	0.9600	C16—F5'	1.381 (10)
C6—C9	1.481 (4)	N1—H1	0.8600
C6—H6	0.9800

F2—C1—F3	108.2 (4)	N1—C9—C6	112.0 (2)
F2—C1—F1	106.3 (4)	C15—C10—C11	119.7 (3)
F3—C1—F1	104.8 (3)	C15—C10—N1	123.9 (3)
F2—C1—C2	112.0 (3)	C11—C10—N1	116.3 (3)
F3—C1—C2	111.9 (3)	C12—C11—C10	120.0 (3)
F1—C1—C2	113.3 (4)	C12—C11—H11	120.0
C3—C2—C1	123.7 (3)	C10—C11—H11	120.0
C3—C2—Cl1	123.3 (3)	C11—C12—C13	120.7 (3)
C1—C2—Cl1	112.9 (3)	C11—C12—H12	119.7
C2—C3—C4	126.0 (3)	C13—C12—H12	119.7
C2—C3—H3	117.0	C14—C13—C12	119.2 (3)
C4—C3—H3	117.0	C14—C13—H13	120.4
C3—C4—C5	121.8 (3)	C12—C13—H13	120.4
C3—C4—C6	122.9 (2)	C13—C14—C15	120.9 (3)
C5—C4—C6	59.8 (2)	C13—C14—C16	120.1 (3)
C3—C4—H4	114.0	C15—C14—C16	119.0 (3)
C5—C4—H4	114.0	C10—C15—C14	119.4 (3)
C6—C4—H4	114.0	C10—C15—H15	120.3
C7—C5—C4	119.9 (3)	C14—C15—H15	120.3
C7—C5—C6	119.1 (3)	F5—C16—F6	113.5 (12)
C4—C5—C6	60.6 (2)	F5—C16—F4'	51.8 (11)
C7—C5—C8	115.5 (4)	F6—C16—F4'	128.8 (9)
C4—C5—C8	115.9 (3)	F5—C16—F6'	132.7 (8)
C6—C5—C8	114.7 (3)	F6—C16—F6'	37.9 (10)
C5—C8—H8B	109.5	F4'—C16—F6'	110.0 (9)
C5—C8—H8A	109.5	F5—C16—F4	104.5 (11)
H8B—C8—H8A	109.5	F6—C16—F4	101.7 (9)
C5—C8—H8C	109.5	F4'—C16—F4	53.9 (6)
H8B—C8—H8C	109.5	F6'—C16—F4	65.7 (9)
H8A—C8—H8C	109.5	F5—C16—F5'	54.8 (12)
C5—C7—H7A	109.5	F6—C16—F5'	65.5 (8)
C5—C7—H7B	109.5	F4'—C16—F5'	102.4 (8)
H7A—C7—H7B	109.5	F6'—C16—F5'	101.0 (10)
C5—C7—H7C	109.5	F4—C16—F5'	139.2 (7)
H7A—C7—H7C	109.5	F5—C16—C14	112.4 (6)
H7B—C7—H7C	109.5	F6—C16—C14	114.7 (6)
C9—C6—C5	121.5 (3)	F4'—C16—C14	115.8 (7)
C9—C6—C4	123.0 (2)	F6'—C16—C14	114.4 (7)
C5—C6—C4	59.6 (2)	F4—C16—C14	108.9 (6)
C9—C6—H6	114.1	F5'—C16—C14	111.6 (5)
C5—C6—H6	114.1	C9—N1—C10	129.3 (2)
C4—C6—H6	114.1	C9—N1—H1	115.4
O1—C9—N1	123.5 (2)	C10—N1—H1	115.4
O1—C9—C6	124.4 (2)

F2—C1—C2—C3	5.3 (6)	C15—C10—C11—C12	0.4 (5)
F3—C1—C2—C3	−116.4 (4)	N1—C10—C11—C12	179.9 (3)
F1—C1—C2—C3	125.5 (4)	C10—C11—C12—C13	−0.2 (5)
F2—C1—C2—Cl1	−176.8 (3)	C11—C12—C13—C14	0.3 (6)
F3—C1—C2—Cl1	61.6 (4)	C12—C13—C14—C15	−0.7 (5)
F1—C1—C2—Cl1	−56.6 (4)	C12—C13—C14—C16	179.4 (4)
C1—C2—C3—C4	175.5 (3)	C11—C10—C15—C14	−0.7 (4)
Cl1—C2—C3—C4	−2.2 (5)	N1—C10—C15—C14	179.8 (3)
C2—C3—C4—C5	−153.3 (3)	C13—C14—C15—C10	0.9 (5)
C2—C3—C4—C6	134.5 (4)	C16—C14—C15—C10	−179.2 (3)
C3—C4—C5—C7	−3.5 (5)	C13—C14—C16—F5	83 (2)
C6—C4—C5—C7	108.7 (3)	C15—C14—C16—F5	−97 (2)
C3—C4—C5—C6	−112.3 (3)	C13—C14—C16—F6	−145.8 (15)
C3—C4—C5—C8	142.7 (3)	C15—C14—C16—F6	34.3 (16)
C6—C4—C5—C8	−105.0 (4)	C13—C14—C16—F4'	25.6 (15)
C7—C5—C6—C9	2.4 (4)	C15—C14—C16—F4'	−154.3 (14)
C4—C5—C6—C9	112.4 (3)	C13—C14—C16—F6'	−103.9 (18)
C8—C5—C6—C9	−140.6 (3)	C15—C14—C16—F6'	76.2 (18)
C7—C5—C6—C4	−110.0 (3)	C13—C14—C16—F4	−32.7 (14)
C8—C5—C6—C4	107.0 (3)	C15—C14—C16—F4	147.4 (14)
C3—C4—C6—C9	0.5 (5)	C13—C14—C16—F5'	142.2 (12)
C5—C4—C6—C9	−109.9 (3)	C15—C14—C16—F5'	−37.7 (13)
C3—C4—C6—C5	110.4 (4)	O1—C9—N1—C10	0.8 (5)
C5—C6—C9—O1	−65.5 (4)	C6—C9—N1—C10	−178.4 (3)
C4—C6—C9—O1	6.5 (5)	C15—C10—N1—C9	−5.4 (5)
C5—C6—C9—N1	113.7 (3)	C11—C10—N1—C9	175.1 (3)
C4—C6—C9—N1	−174.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.15	2.974 (3)	161

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄ClF₆NO
M_r	385.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.006 (3), 16.699 (4), 9.659 (2)
β (°)	93.009 (3)
V (Å³)	1772.8 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.60 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.846, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	7354, 3120, 2247
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.175, 1.04
No. of reflections	3120
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.48

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.15	2.974 (3)	161

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors are very grateful to the Program of the Education Department of Zhejiang Province of China (Y200803060) for financial support.

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, F. H. & Yu, Z. S. (1991). Chem. J. Chin. Univ. 12, 485–487. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, N. B., Shen, D. L., Tan, C. X., Weng, J. Q., Cong, S. & Fu, H. (2008). Chin. J. Org. Chem. 28, 713–717. CAS Google Scholar
Sun, N. B., Shen, D. L., Weng, J. Q., Tan, C. X. & Chen, Q. W. (2007). Chin. Patent CN 101003493. Google Scholar

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Volume 68| Part 6| June 2012| Page o1743

doi:10.1107/S1600536812020922

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

3-(2-Chloro-3,3,3-tri­fluoro­prop-1-en-1-yl)-2,2-di­methyl-N-[3-(tri­fluoro­meth­yl)phen­yl]cyclo­propane­carboxamide

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Acknowledgements

References

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3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethyl-N-[3-(trifluoromethyl)phenyl]cyclopropanecarboxamide