1-{[3-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-2,2-dimethyl­cyclo­propan-1-yl]carbon­yl}-3-(methyl­sulfon­yl)imidazolidin-2-one

Sun, N.-B.; Rao, G.-W.; Chu, J.-B.

doi:10.1107/S1600536812021216

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1744

doi:10.1107/S1600536812021216

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1-{[3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropan-1-yl]carbonyl}-3-(methylsulfonyl)imidazolidin-2-one

Na-Bo Sun,^a Guo-Wu Rao ^b ^* and Jian-Bo Chu ^c

^aCollege of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015, People's Republic of China, ^bCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^cDepartment of Pharmacy, Zhejiang Medical College, Hangzhou 310053, People's Republic of China
^*Correspondence e-mail: rgw@zjut.edu.cn

(Received 7 May 2012; accepted 10 May 2012; online 16 May 2012)

In the title molecule, C₁₃H₁₆ClF₃N₂O₄S, the imidazolidine ring is approximately planar, the largest deviation from this plane being 0.025 (3) Å. The cyclopropane ring forms a dihedral angle of 64.1 (2)° with the imidazolidine ring. In the crystal, C—H⋯O hydrogen bonds are observed.

Related literature

For the biological activities of pyrethroids, see: Chen & Yu (1991 ); Sun et al. (2008 ). For the crystal structures of similar compounds, see: Sun, Shen, Rao et al. (2006 ); Sun, Shen, Zheng et al. (2006 ). For the synthesis of the title compound, see: Sun et al. (2008).

Experimental

Crystal data

C₁₃H₁₆ClF₃N₂O₄S
M_r = 388.79
Monoclinic, P 2₁ /c
a = 15.404 (4) Å
b = 9.483 (2) Å
c = 11.858 (3) Å
β = 103.464 (4)°
V = 1684.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 298 K
0.68 × 0.40 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.761, T_max = 0.930
6863 measured reflections
2964 independent reflections
2548 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.175
S = 1.11
2964 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4ⁱ	0.97	2.50	3.267 (5)	136
C3—H3A⋯O4ⁱⁱ	0.97	2.50	3.352 (6)	146
C13—H13C⋯O2ⁱⁱⁱ	0.96	2.57	3.331 (6)	137
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z.

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/S1600536812021216/wn2475sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021216/wn2475Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021216/wn2475Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812021216/wn2475Isup4.cml

checkCIF report

Comment top

Pyrethroids have a high potential for biological activity with low toxicity and good environmental compatibility. They have been widely used in making pesticides (Chen & Yu, 1991; Sun et al., 2008). In a continuation of our studies of the biological activities of pyrethroids, we have obtained a colourless crystalline compound, whose structure has been confirmed by single-crystal X-ray diffraction. The crystal structures of two similar compounds have already been published (Sun, Shen, Rao et al., 2006; Sun, Shen, Zheng et al., 2006).

The molecular structure of the title compound is illustrated in Fig. 1. Atoms N1, C2, C3, N2 and C1 are approximately planar, the largest deviation from this plane being 0.025 (3) Å for atom N1. The cyclopropane ring (C5—C7) forms dihedral angles of 89.49 (22) ° and 64.07 (21) ° with the least-squares planes of the C8, C9, C6 grouping and the imidazolidine ring, respectively. In the crystal structure, intermolecular C—H···O hydrogen bonds are observed. A short intermolecular contact of O3···C3 = 3.02 Å is present.

Related literature top

For the biological activities of pyrethroids, see: Chen & Yu (1991); Sun et al. (2008). For the crystal structures of similar compounds, see: Sun, Shen, Rao et al. (2006); Sun, Shen, Zheng et al. (2006). For the synthesis of the title compound, see: Sun et al. (2008).

Experimental top

The title compound was synthesized according to the published procedure (Sun et al., 2008). 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 the title compound, shown with 30% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. A portion of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-{[3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2- dimethylcyclopropan-1-yl]carbonyl}-3-(methylsulfonyl)imidazolidin-2-one top

Crystal data top

C₁₃H₁₆ClF₃N₂O₄S	F(000) = 800
M_r = 388.79	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3411 reflections
a = 15.404 (4) Å	θ = 2.7–26.7°
b = 9.483 (2) Å	µ = 0.40 mm⁻¹
c = 11.858 (3) Å	T = 298 K
β = 103.464 (4)°	Block, colourless
V = 1684.5 (8) Å³	0.68 × 0.40 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2964 independent reflections
Radiation source: fine-focus sealed tube	2548 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −18→14
T_min = 0.761, T_max = 0.930	k = −8→11
6863 measured reflections	l = −14→14

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0729P)² + 2.4194P] where P = (F_o² + 2F_c²)/3
2964 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₃H₁₆ClF₃N₂O₄S	V = 1684.5 (8) Å³
M_r = 388.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.404 (4) Å	µ = 0.40 mm⁻¹
b = 9.483 (2) Å	T = 298 K
c = 11.858 (3) Å	0.68 × 0.40 × 0.18 mm
β = 103.464 (4)°

Data collection top

Bruker SMART CCD diffractometer	2964 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2548 reflections with I > 2σ(I)
T_min = 0.761, T_max = 0.930	R_int = 0.022
6863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.11	Δρ_max = 0.57 e Å⁻³
2964 reflections	Δρ_min = −0.53 e Å⁻³
217 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
F1	0.0849 (3)	1.1070 (3)	0.3133 (2)	0.1095 (13)
F2	0.0338 (3)	1.2094 (4)	0.4425 (3)	0.1146 (13)
F3	0.1607 (3)	1.2571 (3)	0.4218 (4)	0.1126 (12)
O3	0.5270 (2)	0.1855 (3)	0.3889 (3)	0.0683 (9)
O4	0.4640 (3)	0.1833 (3)	0.5579 (3)	0.0778 (10)
C13	0.3639 (4)	0.1076 (5)	0.3604 (6)	0.0918 (18)
H13A	0.3575	0.1240	0.2790	0.138*
H13B	0.3101	0.1352	0.3822	0.138*
H13C	0.3749	0.0092	0.3768	0.138*
S	0.45301 (6)	0.20590 (10)	0.43865 (8)	0.0461 (3)
Cl1	0.16342 (14)	1.09317 (14)	0.64639 (11)	0.1095 (7)
O1	0.3400 (2)	0.4131 (3)	0.5463 (2)	0.0605 (8)
O2	0.2822 (2)	0.7813 (3)	0.3499 (2)	0.0585 (7)
N2	0.34790 (19)	0.5737 (3)	0.4009 (2)	0.0407 (7)
N1	0.4231 (2)	0.3728 (3)	0.4092 (3)	0.0450 (7)
C7	0.1933 (2)	0.7923 (3)	0.5495 (3)	0.0385 (7)
H7	0.1997	0.8140	0.6319	0.046*
C10	0.1603 (2)	0.9097 (4)	0.4727 (3)	0.0418 (8)
H10	0.1507	0.8925	0.3935	0.050*
C6	0.1633 (2)	0.6421 (4)	0.5170 (3)	0.0399 (8)
C4	0.2957 (2)	0.6873 (4)	0.4208 (3)	0.0414 (8)
C1	0.3662 (2)	0.4485 (4)	0.4631 (3)	0.0396 (8)
C8	0.1030 (3)	0.6147 (4)	0.3983 (3)	0.0543 (10)
H8A	0.1197	0.6759	0.3424	0.081*
H8B	0.0421	0.6326	0.4007	0.081*
H8C	0.1091	0.5183	0.3767	0.081*
C5	0.2599 (2)	0.6822 (3)	0.5266 (3)	0.0378 (7)
H5	0.3018	0.6469	0.5961	0.045*
C12	0.1041 (3)	1.1499 (4)	0.4206 (4)	0.0608 (11)
C3	0.3890 (3)	0.5794 (4)	0.3006 (3)	0.0505 (9)
H3A	0.4298	0.6584	0.3072	0.061*
H3B	0.3437	0.5882	0.2288	0.061*
C11	0.1428 (3)	1.0371 (4)	0.5035 (3)	0.0492 (9)
C2	0.4380 (3)	0.4417 (5)	0.3047 (4)	0.0604 (11)
H2A	0.4140	0.3856	0.2362	0.072*
H2B	0.5012	0.4573	0.3107	0.072*
C9	0.1443 (3)	0.5501 (4)	0.6126 (4)	0.0527 (9)
H9A	0.0815	0.5302	0.5973	0.079*
H9B	0.1624	0.5983	0.6855	0.079*
H9C	0.1768	0.4633	0.6158	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.183 (4)	0.078 (2)	0.0565 (17)	0.059 (2)	0.0057 (19)	0.0025 (14)
F2	0.117 (3)	0.110 (3)	0.131 (3)	0.074 (2)	0.059 (2)	0.031 (2)
F3	0.130 (3)	0.0571 (18)	0.151 (3)	0.0027 (18)	0.032 (2)	0.032 (2)
O3	0.0670 (19)	0.070 (2)	0.078 (2)	0.0244 (15)	0.0374 (16)	0.0059 (15)
O4	0.119 (3)	0.067 (2)	0.0551 (18)	0.0320 (19)	0.0358 (18)	0.0181 (15)
C13	0.081 (4)	0.057 (3)	0.132 (5)	−0.011 (3)	0.014 (3)	−0.020 (3)
S	0.0538 (6)	0.0429 (5)	0.0461 (5)	0.0096 (4)	0.0209 (4)	0.0010 (4)
Cl1	0.2056 (19)	0.0635 (8)	0.0556 (8)	0.0415 (9)	0.0228 (9)	−0.0150 (6)
O1	0.087 (2)	0.0494 (15)	0.0611 (17)	0.0175 (14)	0.0496 (16)	0.0161 (13)
O2	0.0729 (18)	0.0535 (16)	0.0566 (16)	0.0195 (13)	0.0301 (14)	0.0212 (13)
N2	0.0455 (15)	0.0409 (16)	0.0417 (16)	0.0047 (12)	0.0223 (13)	0.0068 (12)
N1	0.0596 (18)	0.0421 (16)	0.0403 (16)	0.0084 (14)	0.0258 (14)	0.0034 (13)
C7	0.0461 (18)	0.0357 (17)	0.0349 (17)	0.0016 (14)	0.0119 (14)	−0.0058 (14)
C10	0.0476 (19)	0.0396 (18)	0.0400 (18)	0.0045 (15)	0.0137 (15)	−0.0037 (15)
C6	0.0441 (18)	0.0354 (17)	0.0434 (19)	0.0008 (14)	0.0162 (15)	−0.0036 (14)
C4	0.0396 (18)	0.0410 (19)	0.0446 (19)	0.0029 (14)	0.0118 (15)	0.0066 (15)
C1	0.0443 (18)	0.0407 (18)	0.0377 (18)	0.0016 (14)	0.0175 (14)	−0.0009 (14)
C8	0.056 (2)	0.050 (2)	0.055 (2)	−0.0069 (18)	0.0086 (18)	−0.0113 (18)
C5	0.0428 (18)	0.0356 (17)	0.0359 (17)	0.0056 (14)	0.0107 (14)	−0.0008 (13)
C12	0.075 (3)	0.045 (2)	0.066 (3)	0.019 (2)	0.024 (2)	−0.002 (2)
C3	0.061 (2)	0.057 (2)	0.043 (2)	0.0081 (18)	0.0295 (18)	0.0089 (17)
C11	0.062 (2)	0.041 (2)	0.048 (2)	0.0057 (17)	0.0191 (18)	−0.0066 (16)
C2	0.072 (3)	0.069 (3)	0.050 (2)	0.023 (2)	0.036 (2)	0.018 (2)
C9	0.061 (2)	0.047 (2)	0.057 (2)	−0.0048 (18)	0.0284 (19)	−0.0010 (18)

Geometric parameters (Å, º) top

F1—C12	1.303 (5)	C7—H7	0.9800
F2—C12	1.300 (5)	C10—C11	1.308 (5)
F3—C12	1.337 (6)	C10—H10	0.9300
O3—S	1.414 (3)	C6—C9	1.512 (5)
O4—S	1.401 (3)	C6—C5	1.515 (5)
C13—S	1.738 (5)	C6—C8	1.517 (5)
C13—H13A	0.9600	C4—C5	1.484 (5)
C13—H13B	0.9600	C8—H8A	0.9600
C13—H13C	0.9600	C8—H8B	0.9600
S—N1	1.663 (3)	C8—H8C	0.9600
Cl1—C11	1.734 (4)	C5—H5	0.9800
O1—C1	1.197 (4)	C12—C11	1.481 (6)
O2—C4	1.210 (4)	C3—C2	1.503 (6)
N2—C1	1.392 (4)	C3—H3A	0.9700
N2—C4	1.397 (4)	C3—H3B	0.9700
N2—C3	1.472 (4)	C2—H2A	0.9700
N1—C1	1.397 (4)	C2—H2B	0.9700
N1—C2	1.465 (5)	C9—H9A	0.9600
C7—C10	1.453 (5)	C9—H9B	0.9600
C7—C6	1.520 (5)	C9—H9C	0.9600
C7—C5	1.532 (4)

S—C13—H13A	109.5	C6—C8—H8A	109.5
S—C13—H13B	109.5	C6—C8—H8B	109.5
H13A—C13—H13B	109.5	H8A—C8—H8B	109.5
S—C13—H13C	109.5	C6—C8—H8C	109.5
H13A—C13—H13C	109.5	H8A—C8—H8C	109.5
H13B—C13—H13C	109.5	H8B—C8—H8C	109.5
O4—S—O3	118.7 (2)	C4—C5—C6	119.8 (3)
O4—S—N1	108.67 (17)	C4—C5—C7	121.6 (3)
O3—S—N1	104.69 (17)	C6—C5—C7	59.8 (2)
O4—S—C13	110.6 (3)	C4—C5—H5	114.9
O3—S—C13	108.5 (3)	C6—C5—H5	114.9
N1—S—C13	104.6 (2)	C7—C5—H5	114.9
C1—N2—C4	128.4 (3)	F2—C12—F1	108.7 (4)
C1—N2—C3	112.8 (3)	F2—C12—F3	103.9 (4)
C4—N2—C3	118.8 (3)	F1—C12—F3	104.3 (4)
C1—N1—C2	113.3 (3)	F2—C12—C11	114.0 (4)
C1—N1—S	124.4 (2)	F1—C12—C11	112.8 (3)
C2—N1—S	120.8 (2)	F3—C12—C11	112.4 (4)
C10—C7—C6	121.2 (3)	N2—C3—C2	104.4 (3)
C10—C7—C5	124.2 (3)	N2—C3—H3A	110.9
C6—C7—C5	59.5 (2)	C2—C3—H3A	110.9
C10—C7—H7	113.8	N2—C3—H3B	110.9
C6—C7—H7	113.8	C2—C3—H3B	110.9
C5—C7—H7	113.8	H3A—C3—H3B	108.9
C11—C10—C7	126.7 (3)	C10—C11—C12	124.0 (4)
C11—C10—H10	116.7	C10—C11—Cl1	123.6 (3)
C7—C10—H10	116.7	C12—C11—Cl1	112.4 (3)
C9—C6—C5	116.5 (3)	N1—C2—C3	103.8 (3)
C9—C6—C8	114.4 (3)	N1—C2—H2A	111.0
C5—C6—C8	119.4 (3)	C3—C2—H2A	111.0
C9—C6—C7	116.8 (3)	N1—C2—H2B	111.0
C5—C6—C7	60.6 (2)	C3—C2—H2B	111.0
C8—C6—C7	118.7 (3)	H2A—C2—H2B	109.0
O2—C4—N2	117.5 (3)	C6—C9—H9A	109.5
O2—C4—C5	125.1 (3)	C6—C9—H9B	109.5
N2—C4—C5	117.4 (3)	H9A—C9—H9B	109.5
O1—C1—N2	127.6 (3)	C6—C9—H9C	109.5
O1—C1—N1	126.9 (3)	H9A—C9—H9C	109.5
N2—C1—N1	105.5 (3)	H9B—C9—H9C	109.5

O4—S—N1—C1	−37.1 (4)	O2—C4—C5—C6	77.1 (5)
O3—S—N1—C1	−164.9 (3)	N2—C4—C5—C6	−102.0 (4)
C13—S—N1—C1	81.1 (4)	O2—C4—C5—C7	6.2 (5)
O4—S—N1—C2	157.4 (3)	N2—C4—C5—C7	−172.8 (3)
O3—S—N1—C2	29.6 (4)	C9—C6—C5—C4	141.2 (3)
C13—S—N1—C2	−84.4 (4)	C8—C6—C5—C4	−3.0 (5)
C6—C7—C10—C11	144.2 (4)	C7—C6—C5—C4	−111.4 (3)
C5—C7—C10—C11	−143.6 (4)	C9—C6—C5—C7	−107.3 (3)
C10—C7—C6—C9	−139.2 (3)	C8—C6—C5—C7	108.4 (3)
C5—C7—C6—C9	106.9 (3)	C10—C7—C5—C4	−0.6 (5)
C10—C7—C6—C5	113.9 (4)	C6—C7—C5—C4	108.5 (4)
C10—C7—C6—C8	4.4 (5)	C10—C7—C5—C6	−109.1 (4)
C5—C7—C6—C8	−109.5 (3)	C1—N2—C3—C2	−0.5 (4)
C1—N2—C4—O2	−173.8 (3)	C4—N2—C3—C2	−179.1 (3)
C3—N2—C4—O2	4.6 (5)	C7—C10—C11—C12	−176.2 (4)
C1—N2—C4—C5	5.4 (5)	C7—C10—C11—Cl1	4.5 (6)
C3—N2—C4—C5	−176.3 (3)	F2—C12—C11—C10	127.9 (5)
C4—N2—C1—O1	0.5 (6)	F1—C12—C11—C10	3.4 (6)
C3—N2—C1—O1	−177.9 (4)	F3—C12—C11—C10	−114.2 (5)
C4—N2—C1—N1	−178.6 (3)	F2—C12—C11—Cl1	−52.7 (5)
C3—N2—C1—N1	3.0 (4)	F1—C12—C11—Cl1	−177.3 (4)
C2—N1—C1—O1	176.4 (4)	F3—C12—C11—Cl1	65.1 (4)
S—N1—C1—O1	10.0 (6)	C1—N1—C2—C3	4.0 (5)
C2—N1—C1—N2	−4.4 (4)	S—N1—C2—C3	171.0 (3)
S—N1—C1—N2	−170.8 (2)	N2—C3—C2—N1	−2.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.97	2.50	3.267 (5)	136
C3—H3A···O4ⁱⁱ	0.97	2.50	3.352 (6)	146
C13—H13C···O2ⁱⁱⁱ	0.96	2.57	3.331 (6)	137

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆ClF₃N₂O₄S
M_r	388.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.404 (4), 9.483 (2), 11.858 (3)
β (°)	103.464 (4)
V (Å³)	1684.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.68 × 0.40 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.761, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	6863, 2964, 2548
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.175, 1.11
No. of reflections	2964
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.53

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
C2—H2A···O4ⁱ	0.97	2.50	3.267 (5)	136.0
C3—H3A···O4ⁱⁱ	0.97	2.50	3.352 (6)	146.1
C13—H13C···O2ⁱⁱⁱ	0.96	2.57	3.331 (6)	136.5

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.

Acknowledgements

The authors are grateful to the Program of the Education Department of Zhejiang Province of China (grant No. 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., Rao, G.-W., Tan, C.-X. & Weng, J.-Q. (2006). Acta Cryst. E62, o2123–o2124. Web of Science CSD CrossRef 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., Zheng, R.-H., Tan, C.-X. & Weng, J.-Q. (2006). Acta Cryst. E62, o5679–o5680. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1744

doi:10.1107/S1600536812021216

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

1-{[3-(2-Chloro-3,3,3-tri­fluoro­prop-1-en­yl)-2,2-di­methyl­cyclo­propan-1-yl]carbon­yl}-3-(methyl­sulfon­yl)imidazolidin-2-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{[3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropan-1-yl]carbonyl}-3-(methylsulfonyl)imidazolidin-2-one