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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1275

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

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[Vilchez, J. L., Espinosa, P., Arrebola, F. J. & Gonzalez-Casado, A. (1997). Anal. Sci. 13, 817-819.]). For related crystal structures, see: Owen (1976[Owen, J. D. (1976). J. Chem. Soc. Perkin Trans. 1, pp. 1231-1235.]); Babin et al. (1992[Babin, D., Demassey, J., Demoute, J. P., Dutheil, P., Terrie, I. &Tessier, J. (1992). J. Org. Chem. 57, 584-589.]); Lei et al. (2001[Lei, Y. X., Cerioni, G. & Rappoport, Z. (2001). J. Org. Chem. 66, 8379-8394.]).

[Scheme 1]

Experimental

Crystal data
  • C26H21F6NO5

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.979, Tmax = 0.984

  • 24962 measured reflections

  • 3634 independent reflections

  • 2868 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.099

  • S = 1.06

  • 3634 reflections

  • 345 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −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 DA 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[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C—H = 1.00 Å, Uiso = 1.2Ueq(C) for methine C—H, C—H = 0.95 Å, Uiso = 1.2Ueq(C) for Csp2—H and C—H = 0.98 Å, Uiso = 1.5Ueq(C) for CH3 groups. In the absence of significant anomalous scattering effects, Friedel pairs were merged.

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
[Figure 1] 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.
[Figure 2] 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
C26H21F6NO5F(000) = 1112
Mr = 541.44Dx = 1.403 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6226 reflections
a = 7.4932 (2) Åθ = 2.3–23.1°
b = 9.2679 (2) ŵ = 0.13 mm1
c = 36.9165 (8) ÅT = 173 K
V = 2563.71 (10) Å3Plate, colourless
Z = 40.17 × 0.14 × 0.13 mm
Data collection top
Bruker APEXII CCD
diffractometer
3634 independent reflections
Radiation source: fine-focus sealed tube2868 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 79
Tmin = 0.979, Tmax = 0.984k = 1212
24962 measured reflectionsl = 4942
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0327P)2 + 0.8807P]
where P = (Fo2 + 2Fc2)/3
3634 reflections(Δ/σ)max = 0.001
345 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C26H21F6NO5V = 2563.71 (10) Å3
Mr = 541.44Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.4932 (2) ŵ = 0.13 mm1
b = 9.2679 (2) ÅT = 173 K
c = 36.9165 (8) Å0.17 × 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)
Tmin = 0.979, Tmax = 0.984Rint = 0.042
24962 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.06Δρmax = 0.29 e Å3
3634 reflectionsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
F10.9406 (3)0.7188 (4)0.39798 (7)0.1086 (9)
F20.8936 (3)0.6123 (3)0.44823 (6)0.0915 (7)
F30.9197 (3)0.8418 (3)0.44673 (7)0.0964 (8)
F40.5707 (4)0.6522 (2)0.47933 (5)0.0852 (7)
F50.5953 (4)0.8812 (2)0.47448 (6)0.1013 (9)
F60.3792 (3)0.7694 (3)0.44896 (7)0.0873 (7)
O10.6010 (3)0.61863 (19)0.40474 (5)0.0423 (5)
O20.4704 (3)0.7556 (2)0.36230 (5)0.0566 (6)
O30.3658 (3)0.3918 (2)0.25488 (5)0.0545 (6)
O40.3278 (2)0.57874 (18)0.21721 (4)0.0337 (4)
O50.0634 (2)0.6201 (3)0.10760 (5)0.0673 (8)
N10.7583 (4)0.5008 (3)0.20012 (6)0.0564 (7)
C10.8548 (5)0.7284 (4)0.42894 (10)0.0629 (9)
C20.5516 (5)0.7623 (4)0.45687 (9)0.0610 (9)
C30.6580 (4)0.7456 (3)0.42269 (7)0.0431 (7)
H30.63670.83090.40670.052*
C40.5049 (4)0.6380 (3)0.37320 (7)0.0375 (6)
C50.4624 (4)0.4984 (3)0.35754 (6)0.0412 (7)
H50.52420.41630.36650.049*
C60.3425 (4)0.4784 (3)0.33150 (6)0.0412 (7)
H60.33100.38320.32230.049*
C70.2268 (4)0.5881 (3)0.31574 (6)0.0366 (6)
H70.22380.68110.32950.044*
C80.0544 (4)0.5510 (3)0.29675 (7)0.0437 (7)
C90.2095 (4)0.6050 (3)0.27442 (6)0.0384 (6)
H90.19730.70700.26590.046*
C100.0072 (5)0.3963 (4)0.29394 (9)0.0660 (10)
H10B0.09540.33400.28880.099*
H10A0.09470.38770.27430.099*
H10C0.06220.36700.31690.099*
C110.0958 (4)0.6583 (4)0.30134 (9)0.0614 (9)
H11A0.17670.65200.28050.092*
H11B0.04650.75600.30290.092*
H11C0.16170.63640.32360.092*
C120.3083 (4)0.5105 (3)0.24965 (6)0.0378 (6)
C130.4145 (3)0.4969 (3)0.18922 (6)0.0304 (5)
H130.37250.39460.19050.036*
C140.6090 (4)0.4999 (3)0.19511 (6)0.0394 (6)
C150.3567 (3)0.5607 (3)0.15333 (6)0.0278 (5)
C160.4784 (3)0.6086 (3)0.12799 (6)0.0314 (5)
H160.60280.60300.13280.038*
C170.4178 (3)0.6650 (3)0.09551 (6)0.0344 (6)
H170.50140.69830.07810.041*
C180.2380 (3)0.6735 (3)0.08809 (6)0.0339 (6)
H180.19720.71420.06600.041*
C190.1186 (3)0.6220 (3)0.11322 (7)0.0369 (6)
C200.1758 (3)0.5663 (3)0.14596 (6)0.0371 (6)
H200.09180.53210.16320.044*
C210.1298 (3)0.6912 (4)0.07707 (7)0.0426 (7)
C220.1479 (4)0.8371 (4)0.07716 (8)0.0487 (7)
H220.10690.89220.09720.058*
C230.2266 (4)0.9048 (4)0.04787 (9)0.0542 (8)
H230.23921.00680.04770.065*
C240.2859 (4)0.8259 (4)0.01934 (8)0.0506 (8)
H240.34140.87280.00060.061*
C250.2664 (4)0.6809 (4)0.01912 (8)0.0522 (8)
H250.30720.62670.00110.063*
C260.1869 (4)0.6104 (4)0.04824 (8)0.0501 (7)
H260.17270.50860.04810.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0654 (14)0.164 (3)0.0968 (17)0.0054 (18)0.0156 (14)0.0000 (18)
F20.0805 (16)0.0831 (15)0.1108 (17)0.0176 (14)0.0389 (14)0.0186 (14)
F30.0823 (16)0.0920 (17)0.1148 (18)0.0321 (14)0.0483 (15)0.0006 (15)
F40.128 (2)0.0805 (14)0.0467 (10)0.0099 (15)0.0096 (13)0.0122 (11)
F50.148 (2)0.0745 (14)0.0815 (14)0.0317 (17)0.0167 (16)0.0427 (13)
F60.0680 (14)0.0754 (15)0.1185 (19)0.0067 (13)0.0178 (14)0.0171 (15)
O10.0582 (12)0.0328 (9)0.0358 (9)0.0009 (10)0.0143 (9)0.0010 (8)
O20.0780 (16)0.0350 (10)0.0567 (12)0.0099 (11)0.0328 (12)0.0126 (10)
O30.0876 (16)0.0437 (11)0.0322 (9)0.0203 (12)0.0059 (10)0.0060 (9)
O40.0429 (10)0.0363 (9)0.0220 (7)0.0062 (8)0.0007 (7)0.0018 (7)
O50.0226 (9)0.124 (2)0.0551 (12)0.0031 (13)0.0015 (9)0.0512 (14)
N10.0415 (15)0.081 (2)0.0462 (14)0.0060 (15)0.0110 (12)0.0057 (14)
C10.059 (2)0.066 (2)0.063 (2)0.0061 (19)0.0203 (18)0.0057 (19)
C20.079 (3)0.0510 (19)0.0535 (18)0.007 (2)0.0002 (18)0.0089 (17)
C30.0546 (17)0.0342 (13)0.0406 (14)0.0057 (14)0.0144 (13)0.0024 (13)
C40.0439 (16)0.0384 (14)0.0300 (12)0.0039 (13)0.0055 (12)0.0061 (11)
C50.0659 (19)0.0307 (12)0.0270 (12)0.0002 (14)0.0048 (13)0.0051 (11)
C60.0648 (19)0.0347 (13)0.0242 (12)0.0046 (14)0.0021 (13)0.0011 (11)
C70.0490 (16)0.0368 (13)0.0240 (11)0.0020 (12)0.0003 (11)0.0044 (11)
C80.0476 (17)0.0554 (17)0.0281 (12)0.0031 (15)0.0002 (12)0.0086 (12)
C90.0511 (16)0.0399 (13)0.0241 (11)0.0057 (14)0.0019 (11)0.0007 (11)
C100.067 (2)0.073 (2)0.0578 (19)0.024 (2)0.0022 (17)0.0117 (18)
C110.0468 (18)0.086 (3)0.0518 (17)0.0070 (19)0.0022 (15)0.0103 (18)
C120.0481 (16)0.0427 (14)0.0227 (11)0.0023 (13)0.0032 (11)0.0012 (11)
C130.0318 (13)0.0351 (12)0.0242 (11)0.0028 (11)0.0003 (10)0.0005 (10)
C140.0399 (16)0.0500 (16)0.0282 (12)0.0063 (14)0.0058 (11)0.0014 (12)
C150.0297 (13)0.0301 (11)0.0236 (10)0.0003 (10)0.0002 (9)0.0011 (9)
C160.0239 (12)0.0368 (12)0.0335 (12)0.0000 (11)0.0007 (10)0.0002 (11)
C170.0269 (13)0.0485 (15)0.0278 (12)0.0017 (12)0.0062 (10)0.0069 (11)
C180.0309 (13)0.0482 (15)0.0225 (11)0.0012 (12)0.0000 (10)0.0056 (11)
C190.0219 (12)0.0547 (16)0.0342 (12)0.0003 (12)0.0003 (10)0.0084 (13)
C200.0265 (13)0.0551 (16)0.0295 (12)0.0005 (12)0.0050 (10)0.0114 (12)
C210.0184 (12)0.073 (2)0.0368 (14)0.0001 (13)0.0015 (11)0.0218 (14)
C220.0356 (16)0.067 (2)0.0435 (15)0.0086 (15)0.0002 (13)0.0039 (15)
C230.0386 (16)0.0540 (18)0.070 (2)0.0045 (15)0.0009 (15)0.0117 (17)
C240.0356 (16)0.075 (2)0.0418 (16)0.0067 (16)0.0019 (13)0.0170 (16)
C250.0433 (17)0.079 (2)0.0344 (15)0.0005 (17)0.0020 (14)0.0077 (15)
C260.0361 (15)0.0515 (16)0.0627 (19)0.0066 (15)0.0088 (14)0.0013 (16)
Geometric parameters (Å, º) top
F1—C11.315 (4)C10—H10B0.9800
F2—C11.322 (4)C10—H10A0.9800
F3—C11.332 (4)C10—H10C0.9800
F4—C21.322 (4)C11—H11A0.9800
F5—C21.321 (4)C11—H11B0.9800
F6—C21.326 (4)C11—H11C0.9800
O1—C41.381 (3)C13—C141.474 (4)
O1—C31.416 (3)C13—C151.514 (3)
O2—C41.190 (3)C13—H131.0000
O3—C121.197 (3)C15—C161.380 (3)
O4—C121.362 (3)C15—C201.383 (4)
O4—C131.437 (3)C16—C171.385 (3)
O5—C191.380 (3)C16—H160.9500
O5—C211.397 (3)C17—C181.377 (4)
N1—C141.134 (4)C17—H170.9500
C1—C31.501 (5)C18—C191.374 (3)
C2—C31.500 (4)C18—H180.9500
C3—H31.0000C19—C201.383 (3)
C4—C51.453 (4)C20—H200.9500
C5—C61.329 (4)C21—C221.359 (4)
C5—H50.9500C21—C261.370 (4)
C6—C71.457 (4)C22—C231.382 (4)
C6—H60.9500C22—H220.9500
C7—C81.509 (4)C23—C241.357 (4)
C7—C91.539 (3)C23—H230.9500
C7—H71.0000C24—C251.352 (4)
C8—C101.509 (4)C24—H240.9500
C8—C91.510 (4)C25—C261.392 (4)
C8—C111.512 (4)C25—H250.9500
C9—C121.466 (4)C26—H260.9500
C9—H91.0000
C4—O1—C3116.3 (2)H10A—C10—H10C109.5
C12—O4—C13115.84 (19)C8—C11—H11A109.5
C19—O5—C21117.8 (2)C8—C11—H11B109.5
F1—C1—F2107.8 (3)H11A—C11—H11B109.5
F1—C1—F3107.7 (3)C8—C11—H11C109.5
F2—C1—F3107.2 (3)H11A—C11—H11C109.5
F1—C1—C3110.8 (3)H11B—C11—H11C109.5
F2—C1—C3112.7 (3)O3—C12—O4122.0 (2)
F3—C1—C3110.5 (3)O3—C12—C9129.0 (2)
F5—C2—F4108.0 (3)O4—C12—C9109.0 (2)
F5—C2—F6108.0 (3)O4—C13—C14109.3 (2)
F4—C2—F6106.4 (3)O4—C13—C15107.07 (18)
F5—C2—C3111.6 (3)C14—C13—C15113.9 (2)
F4—C2—C3113.0 (3)O4—C13—H13108.8
F6—C2—C3109.7 (3)C14—C13—H13108.8
O1—C3—C2108.6 (2)C15—C13—H13108.8
O1—C3—C1106.2 (3)N1—C14—C13178.9 (3)
C2—C3—C1113.8 (3)C16—C15—C20120.2 (2)
O1—C3—H3109.4C16—C15—C13122.0 (2)
C2—C3—H3109.4C20—C15—C13117.8 (2)
C1—C3—H3109.4C15—C16—C17119.4 (2)
O2—C4—O1121.2 (2)C15—C16—H16120.3
O2—C4—C5129.3 (2)C17—C16—H16120.3
O1—C4—C5109.5 (2)C18—C17—C16121.0 (2)
C6—C5—C4124.1 (3)C18—C17—H17119.5
C6—C5—H5118.0C16—C17—H17119.5
C4—C5—H5118.0C19—C18—C17118.9 (2)
C5—C6—C7126.4 (2)C19—C18—H18120.6
C5—C6—H6116.8C17—C18—H18120.6
C7—C6—H6116.8C18—C19—O5123.1 (2)
C6—C7—C8122.4 (2)C18—C19—C20121.2 (2)
C6—C7—C9121.1 (2)O5—C19—C20115.7 (2)
C8—C7—C959.36 (17)C19—C20—C15119.3 (2)
C6—C7—H7114.4C19—C20—H20120.3
C8—C7—H7114.4C15—C20—H20120.3
C9—C7—H7114.4C22—C21—C26121.0 (3)
C10—C8—C7120.7 (3)C22—C21—O5120.2 (3)
C10—C8—C9120.8 (3)C26—C21—O5118.7 (3)
C7—C8—C961.29 (18)C21—C22—C23119.5 (3)
C10—C8—C11113.9 (3)C21—C22—H22120.2
C7—C8—C11115.8 (2)C23—C22—H22120.2
C9—C8—C11114.6 (3)C24—C23—C22120.1 (3)
C12—C9—C8122.1 (2)C24—C23—H23119.9
C12—C9—C7121.0 (2)C22—C23—H23119.9
C8—C9—C759.35 (17)C25—C24—C23120.3 (3)
C12—C9—H9114.5C25—C24—H24119.8
C8—C9—H9114.5C23—C24—H24119.8
C7—C9—H9114.5C24—C25—C26120.5 (3)
C8—C10—H10B109.5C24—C25—H25119.7
C8—C10—H10A109.5C26—C25—H25119.7
H10B—C10—H10A109.5C21—C26—C25118.5 (3)
C8—C10—H10C109.5C21—C26—H26120.7
H10B—C10—H10C109.5C25—C26—H26120.7
C4—O1—C3—C2109.0 (3)C13—O4—C12—C9176.9 (2)
C4—O1—C3—C1128.2 (3)C8—C9—C12—O346.8 (4)
F5—C2—C3—O1178.4 (3)C7—C9—C12—O324.2 (5)
F4—C2—C3—O159.8 (4)C8—C9—C12—O4132.7 (2)
F6—C2—C3—O158.8 (3)C7—C9—C12—O4156.3 (2)
F5—C2—C3—C163.5 (4)C12—O4—C13—C1479.2 (3)
F4—C2—C3—C158.3 (4)C12—O4—C13—C15157.0 (2)
F6—C2—C3—C1176.8 (3)O4—C13—C14—N173 (21)
F1—C1—C3—O162.5 (4)C15—C13—C14—N1167 (92)
F2—C1—C3—O158.3 (4)O4—C13—C15—C16124.6 (2)
F3—C1—C3—O1178.3 (2)C14—C13—C15—C163.7 (3)
F1—C1—C3—C2178.1 (3)O4—C13—C15—C2057.2 (3)
F2—C1—C3—C261.1 (4)C14—C13—C15—C20178.1 (3)
F3—C1—C3—C258.8 (4)C20—C15—C16—C171.3 (4)
C3—O1—C4—O21.1 (4)C13—C15—C16—C17179.5 (2)
C3—O1—C4—C5178.0 (2)C15—C16—C17—C180.2 (4)
O2—C4—C5—C615.1 (5)C16—C17—C18—C191.4 (4)
O1—C4—C5—C6166.0 (3)C17—C18—C19—O5177.1 (3)
C4—C5—C6—C73.8 (5)C17—C18—C19—C201.9 (4)
C5—C6—C7—C8157.7 (3)C21—O5—C19—C188.8 (5)
C5—C6—C7—C9131.1 (3)C21—O5—C19—C20172.2 (3)
C6—C7—C8—C101.1 (4)C18—C19—C20—C150.8 (5)
C9—C7—C8—C10110.8 (3)O5—C19—C20—C15178.3 (3)
C6—C7—C8—C9109.6 (3)C16—C15—C20—C190.9 (4)
C6—C7—C8—C11145.2 (3)C13—C15—C20—C19179.1 (2)
C9—C7—C8—C11105.2 (3)C19—O5—C21—C2278.7 (4)
C10—C8—C9—C121.0 (4)C19—O5—C21—C26105.6 (3)
C7—C8—C9—C12109.6 (3)C26—C21—C22—C230.5 (5)
C11—C8—C9—C12143.3 (3)O5—C21—C22—C23175.0 (2)
C10—C8—C9—C7110.5 (3)C21—C22—C23—C240.3 (5)
C11—C8—C9—C7107.2 (3)C22—C23—C24—C250.9 (5)
C6—C7—C9—C120.3 (4)C23—C24—C25—C260.6 (5)
C8—C7—C9—C12111.4 (3)C22—C21—C26—C250.8 (4)
C6—C7—C9—C8111.7 (3)O5—C21—C26—C25174.8 (2)
C13—O4—C12—O32.7 (4)C24—C25—C26—C210.2 (5)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C21–C26 phenyl ring.
D—H···AD—HH···AD···AD—H···A
C26—H26···F3i0.952.453.200 (4)135
C17—H17···Cg1ii0.952.513.421 (1)161
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC26H21F6NO5
Mr541.44
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)7.4932 (2), 9.2679 (2), 36.9165 (8)
V3)2563.71 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.17 × 0.14 × 0.13
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.979, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
24962, 3634, 2868
Rint0.042
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.099, 1.06
No. of reflections3634
No. of parameters345
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C26—H26···F3i0.952.453.200 (4)135.4
C17—H17···Cg1ii0.952.513.421 (1)160.9
Symmetry codes: (i) x+1, y1/2, 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

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First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLei, Y. X., Cerioni, G. & Rappoport, Z. (2001). J. Org. Chem. 66, 8379–8394.  Web of Science CrossRef PubMed CAS Google Scholar
First citationOwen, J. D. (1976). J. Chem. Soc. Perkin Trans. 1, pp. 1231–1235.  CrossRef Google Scholar
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationVilchez, 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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