(1SR,3SR)-[(SR)-Cyano­(3-phenoxy­phen­yl)meth­yl] 3-[(Z)-2-chloro-3,3,3-trifluoro­prop-1-en­yl]-2,2-dimethyl­cyclo­propane-1-carboxyl­ate

Cheng, J.; Ju, G.; Dong, J.

doi:10.1107/S1600536808034855

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2253

doi:10.1107/S1600536808034855

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(1SR,3SR)-[(SR)-Cyano(3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate

Jing Cheng,^a Guangxiu Ju ^a and Jinfeng Dong ^a ^*

^aCollege of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, People's Republic of China
^*Correspondence e-mail: mdcj@tom.com

(Received 20 September 2008; accepted 25 October 2008; online 8 November 2008)

In the crystal of the title compound, C₂₃H₁₉ClF₃NO₃, molecules are linked by one C—H⋯O hydrogen bond and two C—H⋯π interactions into a three-dimensional network.

Related literature

For the insecticidal activity of the title compound, see: Anadón et al. (2006 ). For the synthesis, see: Whittle (1991 ).

Experimental

Crystal data

C₂₃H₁₉ClF₃NO₃
M_r = 449.84
Monoclinic, C 2/c
a = 34.7685 (13) Å
b = 7.0159 (3) Å
c = 18.6075 (7) Å
β = 102.113 (1)°
V = 4437.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.927, T_max = 0.957
18537 measured reflections
4361 independent reflections
2721 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.174
S = 1.03
4361 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3ⁱ	0.98	2.39	3.218 (3)	142
C21—H21⋯O3	0.93	2.34	2.984 (3)	126
C19—H19C⋯O3	0.96	2.39	3.037 (3)	124
C5—H5⋯Cg1ⁱⁱ	0.93	2.94	3.721 (1)	143 (1)
C9—H9⋯Cg1ⁱⁱⁱ	0.93	3.06	3.768 (1)	134 (1)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z. Cg1 is the centroid of the C1–C6 ring.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034855/cs2097sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034855/cs2097Isup2.hkl

checkCIF report

Comment top

The title compound, also known as λ-cyhalothrin, exhibits wide-spectrum insecticidal activitiy and represents a good compromise between efficacy and toxicity [Anadón et al., 2006; Whittle, 1991]. In order to research into the relationship between structure and activity, we re-synthesized the title compound and report its crystal structure.

The two benzene rings (defined by atoms C1—C6 and C7—C12, respectively) connected via the O1 atom form a dihedral angle of 89.4 (1)° (Fig.1). The –CF3 group in this appears as a relative rare ordered one which may be due to a close approach of H21···F3 0.93/2.37 Å (idealized: 1.08/2.34 Å) (Table 1). No other unusual features are worth of mention.

In the crystal packing, the molecules at (x, y, z) and (-x + 2, -y + 1, z - 1) are linked together by C13—H13···O3ⁱ interactions (Table 1), forming a dimer. Further analysis (Spek, 2003) indicates that these dimers are joined by C—H···π interactions, forming a three-dimensional network (Fig.2). In more detail, one C—H···π interaction is C5—H5···Cg1ⁱⁱ [C5···Cg1=3.721 (1) Å, C5—H5···Cg1=142.8 (1)°, symmetry code: (ii) 3/2 - x, 1/2 + y, 1/2 - z, Cg1 is the centroid defined by phenyl C atoms C1 to C6] and the other one is C9—H9···Cg1ⁱⁱⁱ(C9···Cg1=3.768 (1) Å, C9—H9···Cg1=134.0 (1)°, symmetry code: (iii) x, y - 1,z].

Related literature top

For the insecticidal activity of the title compound, see: Anadón et al. (2006). For the synthesis, see: Whittle (1991). Cg1 is the centroid of the C1–C6 ring.

Experimental top

The title compound was synthesized according to a standard procedure (Whittle, 1991). Light blue crystals appropriate for data collection were obtained by slow evaporation of a 2-propanol solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure showing the short C—H···O distances as dashed lines.

(1S,3S)-[(S)-Cyano(3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate top

Crystal data top

C₂₃H₁₉ClF₃NO₃	F(000) = 1856
M_r = 449.84	D_x = 1.347 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4557 reflections
a = 34.7685 (13) Å	θ = 2.2–23.4°
b = 7.0159 (3) Å	µ = 0.22 mm⁻¹
c = 18.6075 (7) Å	T = 298 K
β = 102.113 (1)°	Block, light blue
V = 4437.9 (3) Å³	0.30 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4361 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2721 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
0.3° wide ω exposures scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −42→35
T_min = 0.927, T_max = 0.957	k = −8→8
18537 measured reflections	l = −22→22

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1013P)²] where P = (F_o² + 2F_c²)/3
4361 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₃H₁₉ClF₃NO₃	V = 4437.9 (3) Å³
M_r = 449.84	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 34.7685 (13) Å	µ = 0.22 mm⁻¹
b = 7.0159 (3) Å	T = 298 K
c = 18.6075 (7) Å	0.30 × 0.20 × 0.20 mm
β = 102.113 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4361 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2721 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.957	R_int = 0.040
18537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
4361 reflections	Δρ_min = −0.31 e Å⁻³
282 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.82508 (6)	0.7813 (3)	0.26163 (12)	0.0597 (5)
C2	0.82592 (6)	0.7796 (3)	0.33556 (12)	0.0629 (6)
H2	0.8430	0.6989	0.3667	0.076*
C3	0.80102 (8)	0.8999 (4)	0.36309 (14)	0.0784 (7)
H3	0.8010	0.8989	0.4131	0.094*
C4	0.77628 (9)	1.0207 (4)	0.31715 (18)	0.0913 (8)
H4	0.7599	1.1027	0.3361	0.110*
C5	0.77568 (8)	1.0206 (4)	0.24306 (17)	0.0874 (8)
H5	0.7586	1.1016	0.2120	0.105*
C6	0.80008 (7)	0.9018 (3)	0.21453 (13)	0.0737 (7)
H6	0.7998	0.9022	0.1645	0.088*
C7	0.87410 (7)	0.5401 (3)	0.27252 (10)	0.0620 (6)
C8	0.86173 (8)	0.3602 (4)	0.28285 (13)	0.0772 (7)
H8	0.8359	0.3238	0.2632	0.093*
C9	0.88769 (10)	0.2333 (4)	0.32258 (16)	0.0874 (8)
H9	0.8797	0.1089	0.3286	0.105*
C10	0.92547 (9)	0.2877 (3)	0.35373 (13)	0.0758 (7)
H10	0.9427	0.2007	0.3811	0.091*
C11	0.93796 (6)	0.4725 (3)	0.34439 (11)	0.0573 (5)
C12	0.91198 (6)	0.5985 (3)	0.30277 (10)	0.0559 (5)
H12	0.9199	0.7221	0.2951	0.067*
C13	0.97833 (6)	0.5304 (3)	0.38318 (12)	0.0702 (6)
H13	0.9814	0.4949	0.4350	0.084*
C14	0.98580 (8)	0.7324 (5)	0.3802 (2)	0.1129 (12)
C15	1.04198 (6)	0.3962 (3)	0.40121 (11)	0.0623 (6)
C16	1.06771 (6)	0.2730 (3)	0.36835 (11)	0.0636 (6)
H16	1.0583	0.2473	0.3158	0.076*
C17	1.09040 (6)	0.1102 (3)	0.41174 (12)	0.0649 (6)
C18	1.11249 (7)	0.2809 (3)	0.39356 (12)	0.0645 (6)
H18	1.1265	0.2579	0.3539	0.077*
C19	1.08716 (8)	0.0740 (4)	0.48990 (14)	0.0892 (8)
H19A	1.1095	0.0016	0.5145	0.134*
H19B	1.0635	0.0040	0.4904	0.134*
H19C	1.0864	0.1935	0.5147	0.134*
C20	1.09345 (9)	−0.0686 (4)	0.36638 (17)	0.0966 (9)
H20A	1.0969	−0.0324	0.3184	0.145*
H20B	1.0698	−0.1424	0.3619	0.145*
H20C	1.1156	−0.1434	0.3904	0.145*
C21	1.13247 (7)	0.4171 (3)	0.44884 (12)	0.0647 (6)
H21	1.1173	0.4799	0.4770	0.078*
C22	1.16996 (7)	0.4567 (3)	0.46149 (12)	0.0679 (6)
C23	1.18909 (8)	0.6047 (4)	0.51402 (15)	0.0848 (8)
Cl1	1.20240 (2)	0.34527 (17)	0.41744 (5)	0.1270 (4)
F1	1.21955 (6)	0.5406 (3)	0.56238 (9)	0.1209 (6)
F2	1.20212 (7)	0.7498 (3)	0.48102 (12)	0.1395 (8)
F3	1.16466 (6)	0.6767 (3)	0.55237 (11)	0.1256 (7)
N1	0.99126 (9)	0.8901 (5)	0.3787 (3)	0.183 (2)
O1	0.84875 (5)	0.6664 (3)	0.22854 (8)	0.0822 (5)
O2	1.00732 (4)	0.4254 (2)	0.35359 (7)	0.0663 (4)
O3	1.04889 (5)	0.4637 (3)	0.46189 (8)	0.0848 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0391 (11)	0.0637 (13)	0.0713 (13)	−0.0075 (10)	0.0002 (10)	0.0006 (10)
C2	0.0509 (13)	0.0650 (13)	0.0686 (13)	−0.0005 (11)	0.0028 (10)	0.0014 (10)
C3	0.0761 (18)	0.0697 (15)	0.0884 (16)	0.0005 (13)	0.0146 (14)	−0.0031 (13)
C4	0.0773 (19)	0.0685 (16)	0.128 (2)	0.0105 (14)	0.0213 (17)	−0.0024 (17)
C5	0.0674 (17)	0.0660 (16)	0.119 (2)	0.0060 (13)	−0.0019 (15)	0.0178 (15)
C6	0.0554 (14)	0.0761 (15)	0.0808 (14)	−0.0074 (13)	−0.0056 (12)	0.0131 (13)
C7	0.0586 (14)	0.0718 (15)	0.0553 (11)	0.0046 (11)	0.0112 (10)	−0.0011 (10)
C8	0.0673 (16)	0.0902 (19)	0.0738 (14)	−0.0221 (15)	0.0141 (12)	−0.0038 (13)
C9	0.108 (2)	0.0645 (16)	0.0941 (18)	−0.0241 (16)	0.0301 (17)	−0.0003 (14)
C10	0.0889 (19)	0.0599 (15)	0.0778 (14)	0.0141 (14)	0.0157 (14)	0.0110 (12)
C11	0.0534 (13)	0.0582 (13)	0.0603 (11)	0.0078 (10)	0.0123 (9)	−0.0030 (10)
C12	0.0518 (13)	0.0520 (11)	0.0639 (11)	0.0010 (10)	0.0120 (10)	0.0011 (9)
C13	0.0504 (14)	0.0838 (17)	0.0741 (13)	0.0169 (12)	0.0080 (11)	−0.0148 (12)
C14	0.0446 (15)	0.089 (2)	0.198 (4)	0.0039 (15)	0.0085 (18)	−0.043 (2)
C15	0.0502 (13)	0.0796 (15)	0.0567 (12)	0.0140 (11)	0.0105 (10)	0.0005 (11)
C16	0.0570 (14)	0.0797 (15)	0.0551 (11)	0.0162 (11)	0.0140 (10)	−0.0037 (10)
C17	0.0475 (12)	0.0663 (14)	0.0805 (14)	0.0074 (11)	0.0129 (10)	0.0040 (11)
C18	0.0540 (13)	0.0745 (15)	0.0702 (13)	0.0096 (11)	0.0245 (10)	−0.0003 (11)
C19	0.0715 (17)	0.100 (2)	0.0950 (17)	−0.0010 (14)	0.0155 (13)	0.0306 (15)
C20	0.0759 (19)	0.0710 (16)	0.141 (2)	0.0087 (14)	0.0185 (17)	−0.0167 (16)
C21	0.0573 (15)	0.0660 (14)	0.0759 (13)	0.0057 (11)	0.0256 (11)	0.0025 (11)
C22	0.0564 (15)	0.0767 (15)	0.0733 (13)	0.0060 (12)	0.0194 (11)	0.0116 (12)
C23	0.0679 (18)	0.0958 (19)	0.0901 (17)	−0.0137 (15)	0.0157 (15)	0.0084 (16)
Cl1	0.0578 (5)	0.2056 (10)	0.1202 (6)	0.0220 (5)	0.0247 (4)	−0.0386 (6)
F1	0.0990 (13)	0.1413 (15)	0.1050 (12)	−0.0063 (11)	−0.0183 (10)	0.0062 (11)
F2	0.1411 (17)	0.1298 (15)	0.1407 (15)	−0.0612 (13)	0.0139 (13)	0.0315 (12)
F3	0.1030 (14)	0.1286 (15)	0.1494 (15)	−0.0232 (11)	0.0360 (12)	−0.0558 (12)
N1	0.075 (2)	0.086 (2)	0.377 (6)	−0.0026 (17)	0.022 (3)	−0.054 (3)
O1	0.0645 (10)	0.1168 (14)	0.0603 (9)	0.0232 (10)	0.0019 (8)	0.0091 (9)
O2	0.0542 (9)	0.0836 (11)	0.0590 (8)	0.0222 (8)	0.0071 (7)	−0.0039 (7)
O3	0.0577 (10)	0.1282 (14)	0.0655 (9)	0.0242 (9)	0.0065 (7)	−0.0257 (9)

Geometric parameters (Å, º) top

C1—C2	1.370 (3)	C13—H13	0.9800
C1—C6	1.385 (3)	C14—N1	1.124 (4)
C1—O1	1.386 (3)	C15—O3	1.201 (2)
C2—C3	1.382 (3)	C15—O2	1.353 (2)
C2—H2	0.9300	C15—C16	1.467 (3)
C3—C4	1.371 (4)	C16—C17	1.521 (3)
C3—H3	0.9300	C16—C18	1.530 (3)
C4—C5	1.374 (4)	C16—H16	0.9800
C4—H4	0.9300	C17—C18	1.499 (3)
C5—C6	1.373 (4)	C17—C19	1.504 (3)
C5—H5	0.9300	C17—C20	1.528 (3)
C6—H6	0.9300	C18—C21	1.468 (3)
C7—C8	1.360 (3)	C18—H18	0.9800
C7—C12	1.381 (3)	C19—H19A	0.9600
C7—O1	1.389 (3)	C19—H19B	0.9600
C8—C9	1.369 (4)	C19—H19C	0.9600
C8—H8	0.9300	C20—H20A	0.9600
C9—C10	1.374 (4)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600
C10—C11	1.390 (3)	C21—C22	1.305 (3)
C10—H10	0.9300	C21—H21	0.9300
C11—C12	1.379 (3)	C22—C23	1.485 (4)
C11—C13	1.494 (3)	C22—Cl1	1.716 (2)
C12—H12	0.9300	C23—F1	1.317 (3)
C13—C14	1.444 (4)	C23—F2	1.317 (3)
C13—O2	1.448 (2)	C23—F3	1.319 (3)

C2—C1—C6	121.3 (2)	O2—C15—C16	110.69 (17)
C2—C1—O1	123.49 (19)	C15—C16—C17	121.01 (18)
C6—C1—O1	115.2 (2)	C15—C16—C18	121.43 (18)
C1—C2—C3	118.9 (2)	C17—C16—C18	58.87 (14)
C1—C2—H2	120.5	C15—C16—H16	114.7
C3—C2—H2	120.5	C17—C16—H16	114.7
C4—C3—C2	120.4 (2)	C18—C16—H16	114.7
C4—C3—H3	119.8	C18—C17—C19	119.9 (2)
C2—C3—H3	119.8	C18—C17—C16	60.88 (14)
C3—C4—C5	120.0 (3)	C19—C17—C16	120.3 (2)
C3—C4—H4	120.0	C18—C17—C20	115.7 (2)
C5—C4—H4	120.0	C19—C17—C20	115.1 (2)
C6—C5—C4	120.5 (2)	C16—C17—C20	114.3 (2)
C6—C5—H5	119.7	C21—C18—C17	123.46 (18)
C4—C5—H5	119.7	C21—C18—C16	122.67 (18)
C5—C6—C1	118.8 (2)	C17—C18—C16	60.26 (15)
C5—C6—H6	120.6	C21—C18—H18	113.5
C1—C6—H6	120.6	C17—C18—H18	113.5
C8—C7—C12	121.4 (2)	C16—C18—H18	113.5
C8—C7—O1	119.6 (2)	C17—C19—H19A	109.5
C12—C7—O1	119.0 (2)	C17—C19—H19B	109.5
C7—C8—C9	119.2 (2)	H19A—C19—H19B	109.5
C7—C8—H8	120.4	C17—C19—H19C	109.5
C9—C8—H8	120.4	H19A—C19—H19C	109.5
C8—C9—C10	120.7 (2)	H19B—C19—H19C	109.5
C8—C9—H9	119.6	C17—C20—H20A	109.5
C10—C9—H9	119.6	C17—C20—H20B	109.5
C9—C10—C11	120.2 (2)	H20A—C20—H20B	109.5
C9—C10—H10	119.9	C17—C20—H20C	109.5
C11—C10—H10	119.9	H20A—C20—H20C	109.5
C12—C11—C10	118.9 (2)	H20B—C20—H20C	109.5
C12—C11—C13	122.4 (2)	C22—C21—C18	124.9 (2)
C10—C11—C13	118.7 (2)	C22—C21—H21	117.5
C11—C12—C7	119.7 (2)	C18—C21—H21	117.5
C11—C12—H12	120.2	C21—C22—C23	124.1 (2)
C7—C12—H12	120.2	C21—C22—Cl1	123.29 (19)
C14—C13—O2	109.9 (2)	C23—C22—Cl1	112.62 (18)
C14—C13—C11	114.0 (2)	F1—C23—F2	106.1 (2)
O2—C13—C11	109.65 (17)	F1—C23—F3	106.1 (2)
C14—C13—H13	107.7	F2—C23—F3	106.3 (3)
O2—C13—H13	107.7	F1—C23—C22	113.3 (2)
C11—C13—H13	107.7	F2—C23—C22	112.6 (2)
N1—C14—C13	179.0 (4)	F3—C23—C22	111.9 (2)
O3—C15—O2	122.07 (19)	C1—O1—C7	118.18 (16)
O3—C15—C16	127.24 (19)	C15—O2—C13	115.04 (15)

C6—C1—C2—C3	0.5 (3)	C15—C16—C17—C20	142.7 (2)
O1—C1—C2—C3	−179.9 (2)	C18—C16—C17—C20	−107.0 (2)
C1—C2—C3—C4	−0.9 (4)	C19—C17—C18—C21	1.4 (3)
C2—C3—C4—C5	1.0 (4)	C16—C17—C18—C21	111.6 (2)
C3—C4—C5—C6	−0.8 (4)	C20—C17—C18—C21	−143.6 (2)
C4—C5—C6—C1	0.4 (4)	C19—C17—C18—C16	−110.2 (2)
C2—C1—C6—C5	−0.3 (3)	C20—C17—C18—C16	104.8 (2)
O1—C1—C6—C5	−179.9 (2)	C15—C16—C18—C21	−3.2 (3)
C12—C7—C8—C9	−1.6 (3)	C17—C16—C18—C21	−112.8 (2)
O1—C7—C8—C9	176.0 (2)	C15—C16—C18—C17	109.7 (2)
C7—C8—C9—C10	2.0 (4)	C17—C18—C21—C22	121.1 (3)
C8—C9—C10—C11	−0.8 (4)	C16—C18—C21—C22	−165.3 (2)
C9—C10—C11—C12	−0.8 (3)	C18—C21—C22—C23	175.5 (2)
C9—C10—C11—C13	175.9 (2)	C18—C21—C22—Cl1	−3.1 (3)
C10—C11—C12—C7	1.2 (3)	C21—C22—C23—F1	127.1 (3)
C13—C11—C12—C7	−175.40 (18)	Cl1—C22—C23—F1	−54.1 (3)
C8—C7—C12—C11	0.0 (3)	C21—C22—C23—F2	−112.6 (3)
O1—C7—C12—C11	−177.66 (17)	Cl1—C22—C23—F2	66.2 (3)
C12—C11—C13—C14	6.9 (3)	C21—C22—C23—F3	7.1 (3)
C10—C11—C13—C14	−169.7 (2)	Cl1—C22—C23—F3	−174.13 (19)
C12—C11—C13—O2	−116.8 (2)	C2—C1—O1—C7	1.3 (3)
C10—C11—C13—O2	66.6 (3)	C6—C1—O1—C7	−179.1 (2)
O3—C15—C16—C17	43.6 (4)	C8—C7—O1—C1	90.7 (2)
O2—C15—C16—C17	−135.4 (2)	C12—C7—O1—C1	−91.6 (2)
O3—C15—C16—C18	−26.5 (4)	O3—C15—O2—C13	−4.7 (3)
O2—C15—C16—C18	154.5 (2)	C16—C15—O2—C13	174.40 (18)
C15—C16—C17—C18	−110.3 (2)	C14—C13—O2—C15	82.4 (3)
C15—C16—C17—C19	−0.7 (3)	C11—C13—O2—C15	−151.59 (19)
C18—C16—C17—C19	109.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.98	2.39	3.218 (3)	142
C21—H21···O3	0.93	2.34	2.984 (3)	126
C19—H19C···O3	0.96	2.39	3.037 (3)	124
C21—H21···F3	0.93	2.37	2.716 (2)	102
C5—H5···Cg1ⁱⁱ	0.93	2.94	3.721 (1)	143 (1)
C9—H9···Cg1ⁱⁱⁱ	0.93	?	3.768 (1)	134 (1)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉ClF₃NO₃
M_r	449.84
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	34.7685 (13), 7.0159 (3), 18.6075 (7)
β (°)	102.113 (1)
V (Å³)	4437.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.927, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	18537, 4361, 2721
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.174, 1.03
No. of reflections	4361
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.98	2.39	3.218 (3)	142
C21—H21···O3	0.93	2.34	2.984 (3)	126
C19—H19C···O3	0.96	2.39	3.037 (3)	124
C21—H21···F3	0.93	2.370	2.716 (2)	102
C5—H5···Cg1ⁱⁱ	0.93	2.94	3.721 (1)	142.8 (1)
C9—H9···Cg1ⁱⁱⁱ	0.93	?	3.768 (1)	134.0 (1)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x, y−1, z.

Acknowledgements

The authors are grateful to Wuhan Science and Technology program (No. 200760423155) financial support.

References

Anadón, A., Martínez, M., Martínez, M. A., Díaz, M. J. & Martínez-Larranga, M. R. (2006). Toxicol. Lett. 165, 47–49. Web of Science PubMed Google Scholar
Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Whittle, A. J. (1991). British Patent No. GB 2 243 830. Google Scholar

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Volume 64| Part 12| December 2008| Page o2253

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

(1SR,3SR)-[(SR)-Cyano­(3-phen­oxy­phen­yl)meth­yl] 3-[(Z)-2-chloro-3,3,3-tri­fluoro­prop-1-en­yl]-2,2-di­methyl­cyclo­propane-1-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1SR,3SR)-[(SR)-Cyano(3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate