Acrinathrin: (S)-cyano­(3-phen­oxy­phenyl)methyl (Z)-(1R,3S)-2,2-dimethyl-3-{2-[2,2,2-trifluoro-1-(trifluoro­methyl)eth­oxy­carbon­yl]vin­yl}cyclo­propane-1-carboxyl­ate

Yang, H.; Kim, T.H.; Park, K.-M.; Kim, J.

doi:10.1107/S1600536811014760

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1275

doi:10.1107/S1600536811014760

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Acrinathrin: (S)-cyano(3-phenoxyphenyl)methyl (Z)-(1R,3S)-2,2-dimethyl-3-{2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxycarbonyl]vinyl}cyclopropane-1-carboxylate

Hojin Yang,^a Tae Ho Kim,^a ^* Ki-Min Park ^a and Jineun Kim ^a ^*

^aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

(Received 15 April 2011; accepted 20 April 2011; online 29 April 2011)

In the title compound, C₂₆H₂₁F₆NO₅, the dihedral angle between the cyclopropane ring plane and the vinyl group plane is 79.3 (3)°. The dihedral angle between the benzene and phenyl ring planes in the phenoxybenzyl group is 82.7 (1)°. In the crystal structure, weak intermolecular C—H⋯π interactions and C—H⋯F hydrogen bonds contribute to the stabilization of the packing.

Related literature

For information on the insecticidal activity of the title compound, see: Vilchez et al. (1997 ). For related crystal structures, see: Owen (1976 ); Babin et al. (1992 ); Lei et al. (2001 ).

Experimental

Crystal data

C₂₆H₂₁F₆NO₅
M_r = 541.44
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.4932 (2) Å
b = 9.2679 (2) Å
c = 36.9165 (8) Å
V = 2563.71 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 173 K
0.17 × 0.14 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.984
24962 measured reflections
3634 independent reflections
2868 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.099
S = 1.06
3634 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C21–C26 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯F3ⁱ	0.95	2.45	3.200 (4)	135
C17—H17⋯Cg1ⁱⁱ	0.95	2.51	3.421 (1)	161
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014760/wn2431sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014760/wn2431Isup2.hkl

checkCIF report

Comment top

Acrinathrin (systematic name: (S)-α-cyano-3-phenoxybenzyl (Z)-(1R,3S)-2,2-dimethyl-3-[2- (2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl)vinyl] cyclopropanecarboxylate), is a synthetic pyrethroid with high insecticidal activity aganist a wide range of insect pests (Vilchez et al., 1997). However its crystal structure has not yet been reported.

In the title compound (Scheme 1, Fig. 1), the absolute configurations for the three chiral centres of the molecule have been determined using the information provided by the Dr Ehrenstorfer GmbH Company. The dihedral angle between the cyclopropane ring plane and the vinyl group plane is 79.3 (3)°. The dihedral angle between the benzene and phenyl ring planes in the phenoxybenzyl group is 82.7 (1)°. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Lei et al., 2001).

In the crystal structure (Fig. 2) weak C—H···F hydrogen bonds are observed (Table 1). Weak intermolecular C—H···π interactions also exist [C17···Cg1ⁱⁱ 3.421 (1) Å. Cg1 is the centroid of the C21–C26 ring. (Symmetry codes: (ii) x + 1, y, z). These intermolecular interactions may contribute to the stabilization of the packing.

Related literature top

For information on the insecticidal activity of the title compound, see: Vilchez et al. (1997). For related crystal structures, see: Lei et al. (2001).

Experimental top

The title compound was purchased from the Dr Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Fig. 2. Crystal packing of the title compound with weak intermolecular C—H···π interactions and C—H···F hydrogen bonds shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. (Symmetry codes: (i) x - 1, y - 1/2, -z + 1/2; (ii) x + 1, y, z; (iii) -x + 1, y + 1/2, -z + 1/2; (iv) -x + 1.5, -y + 1, z + 1/2; (v) x + 1/2, -y + 1.5, -z + 1; (vi) -x + 1/2, -y + 1, z + 1/2; (vii) x + 1/2, -y + 1/2, -z + 1).

(S)-cyano(3-phenoxyphenyl)methyl (Z)-(1R,3S)-2,2-dimethyl-3-{2-[2,2,2-trifluoro-1- (trifluoromethyl)ethoxycarbonyl]vinyl}cyclopropane-1-carboxylate top

Crystal data top

C₂₆H₂₁F₆NO₅	F(000) = 1112
M_r = 541.44	D_x = 1.403 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6226 reflections
a = 7.4932 (2) Å	θ = 2.3–23.1°
b = 9.2679 (2) Å	µ = 0.13 mm⁻¹
c = 36.9165 (8) Å	T = 173 K
V = 2563.71 (10) Å³	Plate, colourless
Z = 4	0.17 × 0.14 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	3634 independent reflections
Radiation source: fine-focus sealed tube	2868 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
T_min = 0.979, T_max = 0.984	k = −12→12
24962 measured reflections	l = −49→42

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0327P)² + 0.8807P] where P = (F_o² + 2F_c²)/3
3634 reflections	(Δ/σ)_max = 0.001
345 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₆H₂₁F₆NO₅	V = 2563.71 (10) Å³
M_r = 541.44	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.4932 (2) Å	µ = 0.13 mm⁻¹
b = 9.2679 (2) Å	T = 173 K
c = 36.9165 (8) Å	0.17 × 0.14 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	3634 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2868 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.984	R_int = 0.042
24962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.06	Δρ_max = 0.29 e Å⁻³
3634 reflections	Δρ_min = −0.20 e Å⁻³
345 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	0.9406 (3)	0.7188 (4)	0.39798 (7)	0.1086 (9)
F2	0.8936 (3)	0.6123 (3)	0.44823 (6)	0.0915 (7)
F3	0.9197 (3)	0.8418 (3)	0.44673 (7)	0.0964 (8)
F4	0.5707 (4)	0.6522 (2)	0.47933 (5)	0.0852 (7)
F5	0.5953 (4)	0.8812 (2)	0.47448 (6)	0.1013 (9)
F6	0.3792 (3)	0.7694 (3)	0.44896 (7)	0.0873 (7)
O1	0.6010 (3)	0.61863 (19)	0.40474 (5)	0.0423 (5)
O2	0.4704 (3)	0.7556 (2)	0.36230 (5)	0.0566 (6)
O3	0.3658 (3)	0.3918 (2)	0.25488 (5)	0.0545 (6)
O4	0.3278 (2)	0.57874 (18)	0.21721 (4)	0.0337 (4)
O5	−0.0634 (2)	0.6201 (3)	0.10760 (5)	0.0673 (8)
N1	0.7583 (4)	0.5008 (3)	0.20012 (6)	0.0564 (7)
C1	0.8548 (5)	0.7284 (4)	0.42894 (10)	0.0629 (9)
C2	0.5516 (5)	0.7623 (4)	0.45687 (9)	0.0610 (9)
C3	0.6580 (4)	0.7456 (3)	0.42269 (7)	0.0431 (7)
H3	0.6367	0.8309	0.4067	0.052*
C4	0.5049 (4)	0.6380 (3)	0.37320 (7)	0.0375 (6)
C5	0.4624 (4)	0.4984 (3)	0.35754 (6)	0.0412 (7)
H5	0.5242	0.4163	0.3665	0.049*
C6	0.3425 (4)	0.4784 (3)	0.33150 (6)	0.0412 (7)
H6	0.3310	0.3832	0.3223	0.049*
C7	0.2268 (4)	0.5881 (3)	0.31574 (6)	0.0366 (6)
H7	0.2238	0.6811	0.3295	0.044*
C8	0.0544 (4)	0.5510 (3)	0.29675 (7)	0.0437 (7)
C9	0.2095 (4)	0.6050 (3)	0.27442 (6)	0.0384 (6)
H9	0.1973	0.7070	0.2659	0.046*
C10	−0.0072 (5)	0.3963 (4)	0.29394 (9)	0.0660 (10)
H10B	0.0954	0.3340	0.2888	0.099*
H10A	−0.0947	0.3877	0.2743	0.099*
H10C	−0.0622	0.3670	0.3169	0.099*
C11	−0.0958 (4)	0.6583 (4)	0.30134 (9)	0.0614 (9)
H11A	−0.1767	0.6520	0.2805	0.092*
H11B	−0.0465	0.7560	0.3029	0.092*
H11C	−0.1617	0.6364	0.3236	0.092*
C12	0.3083 (4)	0.5105 (3)	0.24965 (6)	0.0378 (6)
C13	0.4145 (3)	0.4969 (3)	0.18922 (6)	0.0304 (5)
H13	0.3725	0.3946	0.1905	0.036*
C14	0.6090 (4)	0.4999 (3)	0.19511 (6)	0.0394 (6)
C15	0.3567 (3)	0.5607 (3)	0.15333 (6)	0.0278 (5)
C16	0.4784 (3)	0.6086 (3)	0.12799 (6)	0.0314 (5)
H16	0.6028	0.6030	0.1328	0.038*
C17	0.4178 (3)	0.6650 (3)	0.09551 (6)	0.0344 (6)
H17	0.5014	0.6983	0.0781	0.041*
C18	0.2380 (3)	0.6735 (3)	0.08809 (6)	0.0339 (6)
H18	0.1972	0.7142	0.0660	0.041*
C19	0.1186 (3)	0.6220 (3)	0.11322 (7)	0.0369 (6)
C20	0.1758 (3)	0.5663 (3)	0.14596 (6)	0.0371 (6)
H20	0.0918	0.5321	0.1632	0.044*
C21	−0.1298 (3)	0.6912 (4)	0.07707 (7)	0.0426 (7)
C22	−0.1479 (4)	0.8371 (4)	0.07716 (8)	0.0487 (7)
H22	−0.1069	0.8922	0.0972	0.058*
C23	−0.2266 (4)	0.9048 (4)	0.04787 (9)	0.0542 (8)
H23	−0.2392	1.0068	0.0477	0.065*
C24	−0.2859 (4)	0.8259 (4)	0.01934 (8)	0.0506 (8)
H24	−0.3414	0.8728	−0.0006	0.061*
C25	−0.2664 (4)	0.6809 (4)	0.01912 (8)	0.0522 (8)
H25	−0.3072	0.6267	−0.0011	0.063*
C26	−0.1869 (4)	0.6104 (4)	0.04824 (8)	0.0501 (7)
H26	−0.1727	0.5086	0.0481	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0654 (14)	0.164 (3)	0.0968 (17)	−0.0054 (18)	0.0156 (14)	0.0000 (18)
F2	0.0805 (16)	0.0831 (15)	0.1108 (17)	0.0176 (14)	−0.0389 (14)	0.0186 (14)
F3	0.0823 (16)	0.0920 (17)	0.1148 (18)	−0.0321 (14)	−0.0483 (15)	0.0006 (15)
F4	0.128 (2)	0.0805 (14)	0.0467 (10)	−0.0099 (15)	0.0096 (13)	0.0122 (11)
F5	0.148 (2)	0.0745 (14)	0.0815 (14)	−0.0317 (17)	0.0167 (16)	−0.0427 (13)
F6	0.0680 (14)	0.0754 (15)	0.1185 (19)	0.0067 (13)	0.0178 (14)	−0.0171 (15)
O1	0.0582 (12)	0.0328 (9)	0.0358 (9)	0.0009 (10)	−0.0143 (9)	0.0010 (8)
O2	0.0780 (16)	0.0350 (10)	0.0567 (12)	−0.0099 (11)	−0.0328 (12)	0.0126 (10)
O3	0.0876 (16)	0.0437 (11)	0.0322 (9)	0.0203 (12)	0.0059 (10)	0.0060 (9)
O4	0.0429 (10)	0.0363 (9)	0.0220 (7)	0.0062 (8)	−0.0007 (7)	0.0018 (7)
O5	0.0226 (9)	0.124 (2)	0.0551 (12)	−0.0031 (13)	−0.0015 (9)	0.0512 (14)
N1	0.0415 (15)	0.081 (2)	0.0462 (14)	0.0060 (15)	−0.0110 (12)	0.0057 (14)
C1	0.059 (2)	0.066 (2)	0.063 (2)	−0.0061 (19)	−0.0203 (18)	0.0057 (19)
C2	0.079 (3)	0.0510 (19)	0.0535 (18)	−0.007 (2)	0.0002 (18)	−0.0089 (17)
C3	0.0546 (17)	0.0342 (13)	0.0406 (14)	−0.0057 (14)	−0.0144 (13)	0.0024 (13)
C4	0.0439 (16)	0.0384 (14)	0.0300 (12)	−0.0039 (13)	−0.0055 (12)	0.0061 (11)
C5	0.0659 (19)	0.0307 (12)	0.0270 (12)	−0.0002 (14)	−0.0048 (13)	0.0051 (11)
C6	0.0648 (19)	0.0347 (13)	0.0242 (12)	−0.0046 (14)	−0.0021 (13)	−0.0011 (11)
C7	0.0490 (16)	0.0368 (13)	0.0240 (11)	−0.0020 (12)	0.0003 (11)	−0.0044 (11)
C8	0.0476 (17)	0.0554 (17)	0.0281 (12)	−0.0031 (15)	−0.0002 (12)	−0.0086 (12)
C9	0.0511 (16)	0.0399 (13)	0.0241 (11)	0.0057 (14)	−0.0019 (11)	−0.0007 (11)
C10	0.067 (2)	0.073 (2)	0.0578 (19)	−0.024 (2)	−0.0022 (17)	−0.0117 (18)
C11	0.0468 (18)	0.086 (3)	0.0518 (17)	0.0070 (19)	0.0022 (15)	−0.0103 (18)
C12	0.0481 (16)	0.0427 (14)	0.0227 (11)	0.0023 (13)	−0.0032 (11)	0.0012 (11)
C13	0.0318 (13)	0.0351 (12)	0.0242 (11)	0.0028 (11)	−0.0003 (10)	0.0005 (10)
C14	0.0399 (16)	0.0500 (16)	0.0282 (12)	0.0063 (14)	−0.0058 (11)	0.0014 (12)
C15	0.0297 (13)	0.0301 (11)	0.0236 (10)	0.0003 (10)	0.0002 (9)	−0.0011 (9)
C16	0.0239 (12)	0.0368 (12)	0.0335 (12)	0.0000 (11)	−0.0007 (10)	−0.0002 (11)
C17	0.0269 (13)	0.0485 (15)	0.0278 (12)	−0.0017 (12)	0.0062 (10)	0.0069 (11)
C18	0.0309 (13)	0.0482 (15)	0.0225 (11)	0.0012 (12)	0.0000 (10)	0.0056 (11)
C19	0.0219 (12)	0.0547 (16)	0.0342 (12)	0.0003 (12)	0.0003 (10)	0.0084 (13)
C20	0.0265 (13)	0.0551 (16)	0.0295 (12)	−0.0005 (12)	0.0050 (10)	0.0114 (12)
C21	0.0184 (12)	0.073 (2)	0.0368 (14)	0.0001 (13)	0.0015 (11)	0.0218 (14)
C22	0.0356 (16)	0.067 (2)	0.0435 (15)	−0.0086 (15)	−0.0002 (13)	−0.0039 (15)
C23	0.0386 (16)	0.0540 (18)	0.070 (2)	0.0045 (15)	0.0009 (15)	0.0117 (17)
C24	0.0356 (16)	0.075 (2)	0.0418 (16)	0.0067 (16)	−0.0019 (13)	0.0170 (16)
C25	0.0433 (17)	0.079 (2)	0.0344 (15)	0.0005 (17)	0.0020 (14)	−0.0077 (15)
C26	0.0361 (15)	0.0515 (16)	0.0627 (19)	0.0066 (15)	0.0088 (14)	0.0013 (16)

Geometric parameters (Å, º) top

F1—C1	1.315 (4)	C10—H10B	0.9800
F2—C1	1.322 (4)	C10—H10A	0.9800
F3—C1	1.332 (4)	C10—H10C	0.9800
F4—C2	1.322 (4)	C11—H11A	0.9800
F5—C2	1.321 (4)	C11—H11B	0.9800
F6—C2	1.326 (4)	C11—H11C	0.9800
O1—C4	1.381 (3)	C13—C14	1.474 (4)
O1—C3	1.416 (3)	C13—C15	1.514 (3)
O2—C4	1.190 (3)	C13—H13	1.0000
O3—C12	1.197 (3)	C15—C16	1.380 (3)
O4—C12	1.362 (3)	C15—C20	1.383 (4)
O4—C13	1.437 (3)	C16—C17	1.385 (3)
O5—C19	1.380 (3)	C16—H16	0.9500
O5—C21	1.397 (3)	C17—C18	1.377 (4)
N1—C14	1.134 (4)	C17—H17	0.9500
C1—C3	1.501 (5)	C18—C19	1.374 (3)
C2—C3	1.500 (4)	C18—H18	0.9500
C3—H3	1.0000	C19—C20	1.383 (3)
C4—C5	1.453 (4)	C20—H20	0.9500
C5—C6	1.329 (4)	C21—C22	1.359 (4)
C5—H5	0.9500	C21—C26	1.370 (4)
C6—C7	1.457 (4)	C22—C23	1.382 (4)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.509 (4)	C23—C24	1.357 (4)
C7—C9	1.539 (3)	C23—H23	0.9500
C7—H7	1.0000	C24—C25	1.352 (4)
C8—C10	1.509 (4)	C24—H24	0.9500
C8—C9	1.510 (4)	C25—C26	1.392 (4)
C8—C11	1.512 (4)	C25—H25	0.9500
C9—C12	1.466 (4)	C26—H26	0.9500
C9—H9	1.0000

C4—O1—C3	116.3 (2)	H10A—C10—H10C	109.5
C12—O4—C13	115.84 (19)	C8—C11—H11A	109.5
C19—O5—C21	117.8 (2)	C8—C11—H11B	109.5
F1—C1—F2	107.8 (3)	H11A—C11—H11B	109.5
F1—C1—F3	107.7 (3)	C8—C11—H11C	109.5
F2—C1—F3	107.2 (3)	H11A—C11—H11C	109.5
F1—C1—C3	110.8 (3)	H11B—C11—H11C	109.5
F2—C1—C3	112.7 (3)	O3—C12—O4	122.0 (2)
F3—C1—C3	110.5 (3)	O3—C12—C9	129.0 (2)
F5—C2—F4	108.0 (3)	O4—C12—C9	109.0 (2)
F5—C2—F6	108.0 (3)	O4—C13—C14	109.3 (2)
F4—C2—F6	106.4 (3)	O4—C13—C15	107.07 (18)
F5—C2—C3	111.6 (3)	C14—C13—C15	113.9 (2)
F4—C2—C3	113.0 (3)	O4—C13—H13	108.8
F6—C2—C3	109.7 (3)	C14—C13—H13	108.8
O1—C3—C2	108.6 (2)	C15—C13—H13	108.8
O1—C3—C1	106.2 (3)	N1—C14—C13	178.9 (3)
C2—C3—C1	113.8 (3)	C16—C15—C20	120.2 (2)
O1—C3—H3	109.4	C16—C15—C13	122.0 (2)
C2—C3—H3	109.4	C20—C15—C13	117.8 (2)
C1—C3—H3	109.4	C15—C16—C17	119.4 (2)
O2—C4—O1	121.2 (2)	C15—C16—H16	120.3
O2—C4—C5	129.3 (2)	C17—C16—H16	120.3
O1—C4—C5	109.5 (2)	C18—C17—C16	121.0 (2)
C6—C5—C4	124.1 (3)	C18—C17—H17	119.5
C6—C5—H5	118.0	C16—C17—H17	119.5
C4—C5—H5	118.0	C19—C18—C17	118.9 (2)
C5—C6—C7	126.4 (2)	C19—C18—H18	120.6
C5—C6—H6	116.8	C17—C18—H18	120.6
C7—C6—H6	116.8	C18—C19—O5	123.1 (2)
C6—C7—C8	122.4 (2)	C18—C19—C20	121.2 (2)
C6—C7—C9	121.1 (2)	O5—C19—C20	115.7 (2)
C8—C7—C9	59.36 (17)	C19—C20—C15	119.3 (2)
C6—C7—H7	114.4	C19—C20—H20	120.3
C8—C7—H7	114.4	C15—C20—H20	120.3
C9—C7—H7	114.4	C22—C21—C26	121.0 (3)
C10—C8—C7	120.7 (3)	C22—C21—O5	120.2 (3)
C10—C8—C9	120.8 (3)	C26—C21—O5	118.7 (3)
C7—C8—C9	61.29 (18)	C21—C22—C23	119.5 (3)
C10—C8—C11	113.9 (3)	C21—C22—H22	120.2
C7—C8—C11	115.8 (2)	C23—C22—H22	120.2
C9—C8—C11	114.6 (3)	C24—C23—C22	120.1 (3)
C12—C9—C8	122.1 (2)	C24—C23—H23	119.9
C12—C9—C7	121.0 (2)	C22—C23—H23	119.9
C8—C9—C7	59.35 (17)	C25—C24—C23	120.3 (3)
C12—C9—H9	114.5	C25—C24—H24	119.8
C8—C9—H9	114.5	C23—C24—H24	119.8
C7—C9—H9	114.5	C24—C25—C26	120.5 (3)
C8—C10—H10B	109.5	C24—C25—H25	119.7
C8—C10—H10A	109.5	C26—C25—H25	119.7
H10B—C10—H10A	109.5	C21—C26—C25	118.5 (3)
C8—C10—H10C	109.5	C21—C26—H26	120.7
H10B—C10—H10C	109.5	C25—C26—H26	120.7

C4—O1—C3—C2	109.0 (3)	C13—O4—C12—C9	−176.9 (2)
C4—O1—C3—C1	−128.2 (3)	C8—C9—C12—O3	−46.8 (4)
F5—C2—C3—O1	−178.4 (3)	C7—C9—C12—O3	24.2 (5)
F4—C2—C3—O1	59.8 (4)	C8—C9—C12—O4	132.7 (2)
F6—C2—C3—O1	−58.8 (3)	C7—C9—C12—O4	−156.3 (2)
F5—C2—C3—C1	63.5 (4)	C12—O4—C13—C14	−79.2 (3)
F4—C2—C3—C1	−58.3 (4)	C12—O4—C13—C15	157.0 (2)
F6—C2—C3—C1	−176.8 (3)	O4—C13—C14—N1	73 (21)
F1—C1—C3—O1	62.5 (4)	C15—C13—C14—N1	−167 (92)
F2—C1—C3—O1	−58.3 (4)	O4—C13—C15—C16	124.6 (2)
F3—C1—C3—O1	−178.3 (2)	C14—C13—C15—C16	3.7 (3)
F1—C1—C3—C2	−178.1 (3)	O4—C13—C15—C20	−57.2 (3)
F2—C1—C3—C2	61.1 (4)	C14—C13—C15—C20	−178.1 (3)
F3—C1—C3—C2	−58.8 (4)	C20—C15—C16—C17	1.3 (4)
C3—O1—C4—O2	−1.1 (4)	C13—C15—C16—C17	179.5 (2)
C3—O1—C4—C5	178.0 (2)	C15—C16—C17—C18	−0.2 (4)
O2—C4—C5—C6	−15.1 (5)	C16—C17—C18—C19	−1.4 (4)
O1—C4—C5—C6	166.0 (3)	C17—C18—C19—O5	−177.1 (3)
C4—C5—C6—C7	−3.8 (5)	C17—C18—C19—C20	1.9 (4)
C5—C6—C7—C8	−157.7 (3)	C21—O5—C19—C18	−8.8 (5)
C5—C6—C7—C9	131.1 (3)	C21—O5—C19—C20	172.2 (3)
C6—C7—C8—C10	1.1 (4)	C18—C19—C20—C15	−0.8 (5)
C9—C7—C8—C10	110.8 (3)	O5—C19—C20—C15	178.3 (3)
C6—C7—C8—C9	−109.6 (3)	C16—C15—C20—C19	−0.9 (4)
C6—C7—C8—C11	145.2 (3)	C13—C15—C20—C19	−179.1 (2)
C9—C7—C8—C11	−105.2 (3)	C19—O5—C21—C22	−78.7 (4)
C10—C8—C9—C12	−1.0 (4)	C19—O5—C21—C26	105.6 (3)
C7—C8—C9—C12	109.6 (3)	C26—C21—C22—C23	0.5 (5)
C11—C8—C9—C12	−143.3 (3)	O5—C21—C22—C23	−175.0 (2)
C10—C8—C9—C7	−110.5 (3)	C21—C22—C23—C24	0.3 (5)
C11—C8—C9—C7	107.2 (3)	C22—C23—C24—C25	−0.9 (5)
C6—C7—C9—C12	0.3 (4)	C23—C24—C25—C26	0.6 (5)
C8—C7—C9—C12	−111.4 (3)	C22—C21—C26—C25	−0.8 (4)
C6—C7—C9—C8	111.7 (3)	O5—C21—C26—C25	174.8 (2)
C13—O4—C12—O3	2.7 (4)	C24—C25—C26—C21	0.2 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C21–C26 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···F3ⁱ	0.95	2.45	3.200 (4)	135
C17—H17···Cg1ⁱⁱ	0.95	2.51	3.421 (1)	161

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₁F₆NO₅
M_r	541.44
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	7.4932 (2), 9.2679 (2), 36.9165 (8)
V (Å³)	2563.71 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.17 × 0.14 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	24962, 3634, 2868
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.099, 1.06
No. of reflections	3634
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.20

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C21–C26 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···F3ⁱ	0.95	2.45	3.200 (4)	135.4
C17—H17···Cg1ⁱⁱ	0.95	2.51	3.421 (1)	160.9

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

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (grant No. 2010-0009089).

References

Babin, D., Demassey, J., Demoute, J. P., Dutheil, P., Terrie, I. &Tessier, J. (1992). J. Org. Chem. 57, 584–589. CrossRef CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lei, Y. X., Cerioni, G. & Rappoport, Z. (2001). J. Org. Chem. 66, 8379–8394. Web of Science CrossRef PubMed CAS Google Scholar
Owen, J. D. (1976). J. Chem. Soc. Perkin Trans. 1, pp. 1231–1235. CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vilchez, J. L., Espinosa, P., Arrebola, F. J. & Gonzalez-Casado, A. (1997). Anal. Sci. 13, 817–819. CrossRef CAS Google Scholar

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Volume 67| Part 5| May 2011| Page o1275

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

Acrinathrin: (S)-cyano­(3-phen­­oxy­phenyl)methyl (Z)-(1R,3S)-2,2-di­methyl-3-{2-[2,2,2-tri­fluoro-1-(tri­fluoro­methyl)eth­­oxy­carbon­yl]vin­yl}cyclo­propane-1-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Acrinathrin: (S)-cyano(3-phenoxyphenyl)methyl (Z)-(1R,3S)-2,2-dimethyl-3-{2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxycarbonyl]vinyl}cyclopropane-1-carboxylate