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ISSN: 2056-9890

1,3-Phenyl­ene bis­­{3-[2-chloro-4-(tri­fluoro­meth­yl)phen­­oxy]benzoate}

aKey Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: he1208@mail.ccnu.edu.cn

(Received 4 June 2012; accepted 6 July 2012; online 14 July 2012)

In the title compound, C34H18Cl2F6O6, one terminal trifluoro­methyl and one entire 2-chloro-4-(trifluoro­meth­yl)phenyl group are disordered with refined occupancy ratios of 0.715 (11):0.285 (11) and 0.517 (5):0.429 (5), respectively. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into ribbons propagating along the a-axis direction.

Related literature

For the herbicidal activity of phen­oxy­phenyl derivatives, see: Dayan & Allen (2000[Dayan, F. E. & Allen, S. N. (2000). Pest Manage. Sci. 56, 717-722.]). For the structures of related compounds, see: Peng & He (2006[Peng, H. & He, H.-W. (2006). Acta Cryst. E62, o5371-o5372.], 2007[Peng, H. & He, H. W. (2007). Chin. J. Org. Chem. 27, 502-506.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C34H18Cl2F6O6

  • Mr = 707.38

  • Triclinic, [P \overline 1]

  • a = 7.7175 (11) Å

  • b = 8.7399 (12) Å

  • c = 23.973 (3) Å

  • α = 92.986 (2)°

  • β = 98.485 (3)°

  • γ = 92.611 (3)°

  • V = 1594.8 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 292 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 13550 measured reflections

  • 5564 independent reflections

  • 3199 reflections with I > 2σ(I)

  • Rint = 0.062

Refinement
  • R[F2 > 2σ(F2)] = 0.079

  • wR(F2) = 0.257

  • S = 1.00

  • 5564 reflections

  • 528 parameters

  • 215 restraints

  • H-atom parameters constrained

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C20—H20⋯O1i 0.93 2.50 3.412 (5) 166
C10—H10⋯O2ii 0.93 2.59 3.152 (5) 120
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x+1, y, z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

Phenoxyphenyl derivatives exhibit herbicidal activity by interacting with plant metabolism in multiple ways. Many diphenyl ether inhibitors of protoporphyrinogen oxidase contains 2-chloro-4-(trifluoromethyl)phenoxy benzoate moiety, which have been a successful class of herbicides (Dayan & Allen, 2000). The title compound has been prepared as a part our work on the design and synthesis of novel herbicidal compounds.

Fig. 1 shows the crystal structure of the title compound. Bond lengths and angles show normal values (Allen et al., 1987). The terminal trifluoromethyl and one of 2-chloro-4-(trifluoromethyl)phenoxy groups are disordered and required a strongly restrained refinement. The C28···C33 ring, Cg5, is rotated almost 180° to the C28'···C33' ring, Cg6, by dihedral angle 2.79°. In the crystal, molecules are linked via weak intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For the herbicidal activity of phenoxyphenyl derivatives, see: Dayan & Allen (2000). For the structures of related compounds, see: Peng & He (2006, 2007). For bond-length data, see: Allen et al. (1987). [This section ok as edited?]

Experimental top

3-(2-Chloro-4-(trifluoromethyl)phenoxy)benzoyl chloride (0.005 mol) in chloroform was added dropwise at 275–278 K to a stirred solution of phen-1,3-diol (0.0025 mol) and triethylamine (0.005 mol) in chloroform (25 mL). The mixture was stirred at 275–278 K for 1 h, washed with 1% hydrochloric acid solution, followed by sodium hydrogen carbonate and ice water, dried and evaporated. The residue was purified by chromatography (silica gel with 15% acetone in petroleum ether). Recrystallization from ethyl acetate and petroleum ether over 1 week gave colorless blocks of the title compound.

Refinement top

The trifluoromethyl group appeared disordered over two orientations with refined occupancies of 0.715 (11) and 0.285 (11) for the major and minor components, respectively. The distances between six pairs of atoms (F1—F2, F1—F3, F2—F3, F1'-F2', F1'-F3', and F2'-F3') were restrained to be equal with the standard deviation (0.01). A similar split refinement was applied to a disordered 2-chloro-4-(trifluoromethyl)phenoxy group, leading to occupation factors of 0.571 (5), 0.429 (5). The displacement parameters of the disordered atoms were restrained to approximately isotropic behavior. H atoms were geometrically positioned (Csp2—H = 0.93 Å, Cmethine—H = 0.98 Å, Cmethylene—H = 0.97 Å, Cmethyl—H = 0.96 Å) and refined as riding, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and 1.2 for all other H atoms.

Structure description top

Phenoxyphenyl derivatives exhibit herbicidal activity by interacting with plant metabolism in multiple ways. Many diphenyl ether inhibitors of protoporphyrinogen oxidase contains 2-chloro-4-(trifluoromethyl)phenoxy benzoate moiety, which have been a successful class of herbicides (Dayan & Allen, 2000). The title compound has been prepared as a part our work on the design and synthesis of novel herbicidal compounds.

Fig. 1 shows the crystal structure of the title compound. Bond lengths and angles show normal values (Allen et al., 1987). The terminal trifluoromethyl and one of 2-chloro-4-(trifluoromethyl)phenoxy groups are disordered and required a strongly restrained refinement. The C28···C33 ring, Cg5, is rotated almost 180° to the C28'···C33' ring, Cg6, by dihedral angle 2.79°. In the crystal, molecules are linked via weak intermolecular C—H···O hydrogen bonds (Table 1).

For the herbicidal activity of phenoxyphenyl derivatives, see: Dayan & Allen (2000). For the structures of related compounds, see: Peng & He (2006, 2007). For bond-length data, see: Allen et al. (1987). [This section ok as edited?]

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, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, with 50% probability displacement ellipsoids. Disordered parts are represented by their major components, and drawn in broken lines.
1,3-Phenylene bis{3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoate} top
Crystal data top
C34H18Cl2F6O6Z = 2
Mr = 707.38F(000) = 716
Triclinic, P1Dx = 1.473 Mg m3
a = 7.7175 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.7399 (12) ÅCell parameters from 2828 reflections
c = 23.973 (3) Åθ = 2.3–23.0°
α = 92.986 (2)°µ = 0.28 mm1
β = 98.485 (3)°T = 292 K
γ = 92.611 (3)°Block, yellow
V = 1594.8 (4) Å30.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3199 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
φ and ω scansh = 99
13550 measured reflectionsk = 1010
5564 independent reflectionsl = 2528
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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.257H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.154P)2]
where P = (Fo2 + 2Fc2)/3
5564 reflections(Δ/σ)max < 0.001
528 parametersΔρmax = 0.51 e Å3
215 restraintsΔρmin = 0.36 e Å3
Crystal data top
C34H18Cl2F6O6γ = 92.611 (3)°
Mr = 707.38V = 1594.8 (4) Å3
Triclinic, P1Z = 2
a = 7.7175 (11) ÅMo Kα radiation
b = 8.7399 (12) ŵ = 0.28 mm1
c = 23.973 (3) ÅT = 292 K
α = 92.986 (2)°0.30 × 0.20 × 0.20 mm
β = 98.485 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3199 reflections with I > 2σ(I)
13550 measured reflectionsRint = 0.062
5564 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.079215 restraints
wR(F2) = 0.257H-atom parameters constrained
S = 1.00Δρmax = 0.51 e Å3
5564 reflectionsΔρmin = 0.36 e Å3
528 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*/UeqOcc. (<1)
C11.0008 (10)0.4068 (9)0.1855 (3)0.164 (4)
F11.1346 (11)0.3142 (8)0.1888 (3)0.173 (3)0.715 (11)
F20.9704 (16)0.4550 (9)0.1344 (2)0.181 (4)0.715 (11)
F30.8624 (10)0.3082 (8)0.1916 (3)0.178 (3)0.715 (11)
F1'1.1403 (17)0.434 (2)0.1557 (7)0.172 (8)0.285 (11)
F2'0.8633 (17)0.4334 (18)0.1450 (6)0.129 (6)0.285 (11)
F3'0.997 (3)0.2580 (12)0.1905 (9)0.189 (9)0.285 (11)
C21.0228 (9)0.5297 (6)0.2317 (2)0.1074 (18)
C31.0153 (8)0.6824 (6)0.2186 (2)0.1061 (17)
H30.99650.70810.18110.127*
C41.0356 (6)0.7936 (5)0.26078 (19)0.0780 (12)
C51.0635 (5)0.7577 (4)0.31719 (16)0.0606 (9)
C61.0725 (6)0.6045 (5)0.32885 (18)0.0718 (11)
H61.09150.57790.36620.086*
C71.0540 (7)0.4930 (6)0.2868 (2)0.0921 (14)
H71.06270.39080.29550.111*
Cl11.0268 (2)0.98315 (14)0.24459 (6)0.1118 (6)
C81.0931 (5)0.8438 (4)0.41370 (16)0.0633 (10)
C91.2532 (5)0.8562 (5)0.44654 (19)0.0730 (11)
H91.35380.87950.43090.088*
C101.2640 (5)0.8340 (6)0.50298 (19)0.0803 (13)
H101.37270.84490.52580.096*
C111.1163 (5)0.7958 (5)0.52665 (17)0.0727 (12)
H111.12510.77950.56500.087*
C120.9547 (4)0.7821 (4)0.49233 (15)0.0568 (9)
C130.9418 (5)0.8086 (4)0.43542 (16)0.0583 (9)
H130.83330.80280.41240.070*
C140.7901 (5)0.7436 (4)0.51447 (16)0.0605 (10)
C150.6718 (5)0.6869 (4)0.59670 (15)0.0593 (9)
C160.5571 (6)0.5592 (5)0.58476 (17)0.0718 (11)
H160.57280.48340.55750.086*
C170.4200 (7)0.5491 (5)0.6147 (2)0.0841 (13)
H170.34140.46410.60740.101*
C180.3932 (6)0.6588 (5)0.65491 (18)0.0762 (12)
H180.29760.64930.67420.091*
C190.5100 (5)0.7820 (5)0.66599 (16)0.0659 (10)
C200.6535 (5)0.7982 (5)0.63710 (15)0.0629 (10)
H200.73380.88190.64510.075*
C210.4647 (5)1.0363 (5)0.69507 (19)0.0743 (12)
C220.4654 (6)1.1432 (5)0.74417 (19)0.0790 (12)
C230.4556 (8)1.2993 (6)0.7364 (2)0.1024 (16)
H230.44831.33400.70020.123*
C240.4564 (11)1.4006 (7)0.7804 (3)0.135 (2)
H240.45311.50470.77440.162*
C250.4619 (11)1.3539 (8)0.8330 (3)0.146 (3)
H250.46071.42480.86320.175*
C260.4692 (10)1.1990 (7)0.8417 (2)0.121 (2)
C270.4746 (7)1.0952 (6)0.7987 (2)0.0950 (15)
H270.48430.99190.80550.114*
O11.0799 (4)0.8770 (3)0.35637 (11)0.0716 (8)
O20.6463 (3)0.7448 (4)0.48806 (11)0.0797 (9)
O30.8193 (3)0.7046 (3)0.56895 (10)0.0678 (8)
O40.4900 (4)0.8907 (3)0.70907 (11)0.0729 (8)
O50.4436 (5)1.0719 (4)0.64716 (14)0.1047 (11)
C280.4973 (19)1.0073 (12)0.9132 (8)0.114 (8)0.429 (5)
C290.6790 (19)1.0061 (12)0.9252 (7)0.092 (4)0.429 (5)
C300.7572 (13)0.8795 (14)0.9487 (8)0.116 (6)0.429 (5)
H300.87880.87870.95670.139*0.429 (5)
C310.6537 (14)0.7541 (14)0.9603 (10)0.121 (3)0.429 (5)
C320.4720 (14)0.7553 (15)0.9483 (10)0.146 (8)0.429 (5)
H320.40280.67140.95600.175*0.429 (5)
C330.3938 (14)0.8819 (16)0.9247 (8)0.160 (11)0.429 (5)
H330.27220.88270.91670.192*0.429 (5)
Cl20.8236 (8)1.1645 (6)0.9180 (2)0.171 (2)0.429 (5)
C340.7402 (18)0.6295 (15)0.9921 (6)0.176 (4)0.429 (5)
F40.6176 (18)0.5555 (19)1.0149 (8)0.252 (5)0.429 (5)
F50.802 (2)0.5392 (18)0.9542 (6)0.200 (6)0.429 (5)
F60.8722 (19)0.6868 (17)1.0316 (7)0.207 (7)0.429 (5)
O60.4227 (13)1.1471 (13)0.8941 (3)0.083 (3)0.429 (5)
C28'0.5648 (16)1.0452 (12)0.9143 (6)0.099 (5)0.571 (5)
C29'0.4545 (11)0.9259 (14)0.9270 (5)0.104 (4)0.571 (5)
C30'0.5250 (10)0.7945 (13)0.9492 (6)0.122 (4)0.571 (5)
H30'0.45110.71480.95770.146*0.571 (5)
C31'0.7057 (10)0.7824 (13)0.9587 (7)0.121 (3)0.571 (5)
C32'0.8161 (10)0.9016 (14)0.9460 (8)0.172 (8)0.571 (5)
H32'0.93700.89350.95230.207*0.571 (5)
C33'0.7456 (15)1.0330 (12)0.9238 (7)0.153 (7)0.571 (5)
H33'0.81941.11280.91530.184*0.571 (5)
Cl2'0.2398 (7)0.9546 (9)0.9143 (3)0.273 (4)0.571 (5)
C34'0.7793 (14)0.6370 (13)0.9821 (4)0.176 (4)0.571 (5)
F4'0.6955 (18)0.5089 (17)0.9552 (5)0.252 (5)0.571 (5)
F5'0.9484 (12)0.6468 (13)0.9771 (4)0.207 (4)0.571 (5)
F6'0.7642 (15)0.6294 (11)1.0369 (3)0.159 (3)0.571 (5)
O6'0.522 (2)1.1809 (14)0.9002 (3)0.150 (4)0.571 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.272 (12)0.130 (7)0.086 (5)0.012 (8)0.017 (6)0.017 (5)
F10.256 (7)0.111 (5)0.157 (6)0.041 (5)0.058 (5)0.039 (4)
F20.296 (10)0.152 (5)0.091 (4)0.017 (7)0.019 (5)0.012 (3)
F30.235 (7)0.127 (5)0.150 (5)0.012 (5)0.011 (5)0.052 (4)
F1'0.178 (11)0.156 (11)0.176 (12)0.002 (9)0.037 (9)0.054 (9)
F2'0.147 (9)0.120 (9)0.116 (10)0.006 (7)0.017 (7)0.027 (7)
F3'0.200 (13)0.164 (12)0.197 (13)0.012 (10)0.011 (10)0.003 (9)
C20.184 (6)0.074 (3)0.061 (3)0.015 (3)0.005 (3)0.001 (2)
C30.168 (5)0.090 (4)0.054 (3)0.003 (3)0.000 (3)0.010 (3)
C40.094 (3)0.063 (2)0.072 (3)0.004 (2)0.005 (2)0.014 (2)
C50.058 (2)0.065 (2)0.058 (2)0.0022 (17)0.0071 (17)0.0061 (19)
C60.086 (3)0.072 (3)0.058 (2)0.013 (2)0.008 (2)0.012 (2)
C70.130 (4)0.070 (3)0.078 (3)0.020 (3)0.013 (3)0.006 (2)
Cl10.1702 (14)0.0692 (8)0.0854 (9)0.0165 (8)0.0159 (8)0.0242 (6)
C80.068 (3)0.065 (2)0.058 (2)0.0083 (18)0.0104 (19)0.0010 (18)
C90.052 (2)0.088 (3)0.081 (3)0.009 (2)0.014 (2)0.002 (2)
C100.051 (2)0.117 (4)0.071 (3)0.014 (2)0.000 (2)0.002 (3)
C110.055 (2)0.102 (3)0.061 (3)0.020 (2)0.0035 (19)0.001 (2)
C120.051 (2)0.063 (2)0.054 (2)0.0072 (16)0.0043 (16)0.0042 (17)
C130.053 (2)0.060 (2)0.059 (2)0.0023 (16)0.0006 (17)0.0021 (17)
C140.055 (2)0.071 (2)0.054 (2)0.0106 (17)0.0024 (18)0.0021 (18)
C150.062 (2)0.067 (2)0.049 (2)0.0043 (18)0.0061 (17)0.0102 (18)
C160.086 (3)0.069 (3)0.057 (2)0.003 (2)0.003 (2)0.0038 (19)
C170.098 (3)0.082 (3)0.068 (3)0.030 (3)0.006 (3)0.013 (2)
C180.081 (3)0.083 (3)0.067 (3)0.014 (2)0.018 (2)0.021 (2)
C190.076 (3)0.074 (3)0.048 (2)0.004 (2)0.0071 (19)0.0123 (19)
C200.060 (2)0.071 (2)0.056 (2)0.0042 (18)0.0027 (18)0.012 (2)
C210.073 (3)0.095 (3)0.060 (3)0.017 (2)0.012 (2)0.025 (2)
C220.088 (3)0.083 (3)0.069 (3)0.018 (2)0.014 (2)0.013 (2)
C230.140 (5)0.086 (4)0.084 (4)0.023 (3)0.017 (3)0.022 (3)
C240.213 (8)0.079 (4)0.111 (5)0.031 (4)0.013 (5)0.010 (4)
C250.225 (8)0.098 (5)0.106 (5)0.044 (5)0.009 (5)0.011 (4)
C260.197 (7)0.100 (4)0.070 (4)0.055 (4)0.013 (4)0.011 (3)
C270.144 (4)0.080 (3)0.067 (3)0.032 (3)0.022 (3)0.014 (2)
O10.0889 (19)0.0666 (16)0.0598 (17)0.0009 (14)0.0135 (14)0.0058 (13)
O20.0510 (16)0.125 (3)0.0620 (17)0.0010 (15)0.0011 (13)0.0167 (16)
O30.0578 (15)0.0908 (19)0.0541 (16)0.0127 (13)0.0022 (12)0.0080 (13)
O40.095 (2)0.0740 (18)0.0524 (16)0.0045 (15)0.0167 (13)0.0099 (14)
O50.138 (3)0.116 (3)0.068 (2)0.047 (2)0.0216 (19)0.0280 (19)
C280.176 (18)0.107 (16)0.063 (12)0.023 (16)0.049 (12)0.009 (11)
C290.112 (13)0.085 (11)0.075 (10)0.002 (9)0.005 (9)0.001 (8)
C300.097 (10)0.147 (18)0.096 (12)0.010 (11)0.001 (8)0.019 (12)
C310.149 (7)0.126 (6)0.087 (4)0.041 (5)0.007 (5)0.011 (4)
C320.177 (12)0.128 (11)0.134 (12)0.016 (9)0.035 (9)0.006 (9)
C330.162 (14)0.169 (14)0.153 (14)0.030 (10)0.031 (10)0.001 (10)
Cl20.192 (5)0.132 (4)0.175 (5)0.039 (3)0.012 (4)0.035 (3)
C340.197 (7)0.179 (7)0.154 (7)0.029 (6)0.035 (6)0.000 (6)
F40.278 (8)0.222 (8)0.255 (8)0.045 (6)0.017 (6)0.031 (6)
F50.231 (11)0.154 (8)0.217 (10)0.085 (8)0.024 (8)0.002 (7)
F60.190 (10)0.225 (11)0.214 (11)0.042 (8)0.035 (8)0.062 (9)
O60.102 (6)0.090 (6)0.056 (5)0.034 (5)0.003 (4)0.011 (4)
C28'0.155 (15)0.084 (8)0.056 (7)0.045 (10)0.002 (8)0.001 (6)
C29'0.149 (12)0.115 (10)0.044 (6)0.045 (10)0.000 (6)0.008 (6)
C30'0.160 (9)0.123 (8)0.086 (7)0.003 (8)0.036 (7)0.001 (6)
C31'0.149 (7)0.126 (6)0.087 (4)0.041 (5)0.007 (5)0.011 (4)
C32'0.161 (10)0.191 (12)0.158 (12)0.036 (9)0.001 (9)0.005 (9)
C33'0.166 (11)0.153 (12)0.139 (10)0.003 (9)0.027 (9)0.009 (9)
Cl2'0.170 (4)0.396 (10)0.220 (6)0.051 (5)0.027 (4)0.156 (6)
C34'0.197 (7)0.179 (7)0.154 (7)0.029 (6)0.035 (6)0.000 (6)
F4'0.278 (8)0.222 (8)0.255 (8)0.045 (6)0.017 (6)0.031 (6)
F5'0.218 (8)0.225 (8)0.176 (7)0.096 (7)0.003 (6)0.015 (6)
F6'0.207 (8)0.168 (7)0.105 (5)0.036 (6)0.012 (5)0.052 (4)
O6'0.217 (10)0.128 (7)0.096 (6)0.019 (7)0.006 (6)0.010 (5)
Geometric parameters (Å, º) top
C1—F21.307 (7)C21—O41.348 (5)
C1—F3'1.312 (8)C21—C221.464 (6)
C1—F11.337 (7)C22—C271.387 (6)
C1—F2'1.367 (8)C22—C231.391 (7)
C1—F31.372 (7)C23—C241.340 (8)
C1—F1'1.394 (9)C23—H230.9300
C1—C21.487 (8)C24—C251.340 (9)
C2—C71.366 (7)C24—H240.9300
C2—C31.389 (7)C25—C261.383 (8)
C3—C41.353 (6)C25—H250.9300
C3—H30.9300C26—C271.344 (7)
C4—C51.392 (6)C26—O6'1.418 (9)
C4—Cl11.723 (4)C26—O61.444 (9)
C5—O11.355 (5)C27—H270.9300
C5—C61.385 (6)C28—C291.3900
C6—C71.352 (6)C28—C331.3900
C6—H60.9300C28—O61.442 (12)
C7—H70.9300C29—C301.3900
C8—C91.360 (6)C29—Cl21.770 (9)
C8—C131.376 (5)C30—C311.3900
C8—O11.409 (5)C30—H300.9300
C9—C101.368 (6)C31—C321.3900
C9—H90.9300C31—C341.489 (11)
C10—C111.382 (6)C32—C331.3900
C10—H100.9300C32—H320.9300
C11—C121.385 (5)C33—H330.9300
C11—H110.9300C34—F41.321 (9)
C12—C131.386 (5)C34—F51.330 (9)
C12—C141.479 (5)C34—F61.343 (9)
C13—H130.9300C28'—O6'1.295 (13)
C14—O21.195 (4)C28'—C29'1.3900
C14—O31.356 (4)C28'—C33'1.3900
C15—C201.363 (5)C29'—C30'1.3900
C15—C161.384 (6)C29'—Cl2'1.673 (7)
C15—O31.407 (4)C30'—C31'1.3900
C16—C171.365 (6)C30'—H30'0.9300
C16—H160.9300C31'—C32'1.3900
C17—C181.368 (6)C31'—C34'1.517 (10)
C17—H170.9300C32'—C33'1.3900
C18—C191.362 (6)C32'—H32'0.9300
C18—H180.9300C33'—H33'0.9300
C19—C201.396 (5)C34'—F5'1.327 (8)
C19—O41.397 (5)C34'—F6'1.341 (8)
C20—H200.9300C34'—F4'1.351 (9)
C21—O51.196 (5)
F2—C1—F3'117.4 (12)O5—C21—O4122.5 (4)
F2—C1—F1109.1 (6)O5—C21—C22124.4 (4)
F3'—C1—F151.7 (8)O4—C21—C22113.1 (4)
F2—C1—F2'39.9 (6)C27—C22—C23118.1 (4)
F3'—C1—F2'106.4 (8)C27—C22—C21122.6 (4)
F1—C1—F2'135.0 (10)C23—C22—C21119.4 (4)
F2—C1—F3107.1 (7)C24—C23—C22121.0 (5)
F3'—C1—F350.8 (8)C24—C23—H23119.5
F1—C1—F3102.4 (6)C22—C23—H23119.5
F2'—C1—F371.8 (7)C23—C24—C25120.9 (6)
F2—C1—F1'60.3 (7)C23—C24—H24119.5
F3'—C1—F1'103.6 (8)C25—C24—H24119.5
F1—C1—F1'59.1 (8)C24—C25—C26119.2 (6)
F2'—C1—F1'100.0 (7)C24—C25—H25120.4
F3—C1—F1'145.4 (9)C26—C25—H25120.4
F2—C1—C2115.0 (6)C27—C26—C25121.2 (6)
F3'—C1—C2127.5 (11)C27—C26—O6'127.3 (7)
F1—C1—C2113.1 (6)C25—C26—O6'108.8 (7)
F2'—C1—C2110.7 (9)C27—C26—O6118.9 (7)
F3—C1—C2109.3 (6)C25—C26—O6117.8 (6)
F1'—C1—C2105.1 (9)O6'—C26—O632.3 (6)
C7—C2—C3120.0 (4)C26—C27—C22119.5 (5)
C7—C2—C1120.2 (5)C26—C27—H27120.2
C3—C2—C1119.8 (5)C22—C27—H27120.2
C4—C3—C2119.5 (4)C5—O1—C8118.1 (3)
C4—C3—H3120.3C14—O3—C15117.1 (3)
C2—C3—H3120.3C21—O4—C19117.9 (3)
C3—C4—C5121.2 (4)C29—C28—C33120.0
C3—C4—Cl1119.5 (4)C29—C28—O6117.6 (10)
C5—C4—Cl1119.3 (3)C33—C28—O6122.1 (10)
O1—C5—C6125.3 (4)C28—C29—C30120.0
O1—C5—C4116.8 (4)C28—C29—Cl2124.1 (8)
C6—C5—C4117.9 (4)C30—C29—Cl2115.6 (8)
C7—C6—C5121.1 (4)C29—C30—C31120.0
C7—C6—H6119.4C29—C30—H30120.0
C5—C6—H6119.4C31—C30—H30120.0
C6—C7—C2120.2 (4)C32—C31—C30120.0
C6—C7—H7119.9C32—C31—C34121.0 (5)
C2—C7—H7119.9C30—C31—C34118.5 (5)
C9—C8—C13122.0 (4)C33—C32—C31120.0
C9—C8—O1119.2 (4)C33—C32—H32120.0
C13—C8—O1118.7 (3)C31—C32—H32120.0
C8—C9—C10119.0 (4)C32—C33—C28120.0
C8—C9—H9120.5C32—C33—H33120.0
C10—C9—H9120.5C28—C33—H33120.0
C9—C10—C11121.2 (4)F4—C34—F5111.1 (9)
C9—C10—H10119.4F4—C34—F6111.5 (9)
C11—C10—H10119.4F5—C34—F6110.0 (8)
C10—C11—C12118.9 (4)F4—C34—C31106.9 (11)
C10—C11—H11120.6F5—C34—C31106.0 (13)
C12—C11—H11120.6F6—C34—C31111.1 (13)
C11—C12—C13120.3 (4)C28—O6—C26116.3 (10)
C11—C12—C14122.3 (4)O6'—C28'—C29'127.3 (11)
C13—C12—C14117.4 (3)O6'—C28'—C33'112.2 (11)
C8—C13—C12118.5 (3)C29'—C28'—C33'120.0
C8—C13—H13120.7C28'—C29'—C30'120.0
C12—C13—H13120.7C28'—C29'—Cl2'115.6 (8)
O2—C14—O3122.7 (4)C30'—C29'—Cl2'124.4 (8)
O2—C14—C12124.9 (4)C29'—C30'—C31'120.0
O3—C14—C12112.4 (3)C29'—C30'—H30'120.0
C20—C15—C16122.6 (4)C31'—C30'—H30'120.0
C20—C15—O3116.5 (3)C32'—C31'—C30'120.0
C16—C15—O3120.9 (3)C32'—C31'—C34'121.0 (4)
C17—C16—C15117.1 (4)C30'—C31'—C34'119.0 (4)
C17—C16—H16121.4C33'—C32'—C31'120.0
C15—C16—H16121.4C33'—C32'—H32'120.0
C16—C17—C18122.8 (4)C31'—C32'—H32'120.0
C16—C17—H17118.6C32'—C33'—C28'120.0
C18—C17—H17118.6C32'—C33'—H33'120.0
C19—C18—C17118.4 (4)C28'—C33'—H33'120.0
C19—C18—H18120.8F5'—C34'—F6'108.8 (8)
C17—C18—H18120.8F5'—C34'—F4'112.4 (8)
C18—C19—C20121.5 (4)F6'—C34'—F4'106.6 (8)
C18—C19—O4119.1 (4)F5'—C34'—C31'105.2 (7)
C20—C19—O4119.4 (4)F6'—C34'—C31'111.3 (10)
C15—C20—C19117.6 (4)F4'—C34'—C31'112.4 (12)
C15—C20—H20121.2C28'—O6'—C26116.6 (10)
C19—C20—H20121.2
F2—C1—C2—C7179.6 (8)C23—C22—C27—C261.7 (8)
F3'—C1—C2—C74.4 (15)C21—C22—C27—C26178.0 (5)
F1—C1—C2—C754.1 (9)C6—C5—O1—C85.4 (5)
F2'—C1—C2—C7136.4 (9)C4—C5—O1—C8174.6 (3)
F3—C1—C2—C759.2 (8)C9—C8—O1—C5101.9 (4)
F1'—C1—C2—C7116.5 (11)C13—C8—O1—C581.9 (4)
F2—C1—C2—C31.8 (11)O2—C14—O3—C159.2 (5)
F3'—C1—C2—C3177.0 (13)C12—C14—O3—C15171.2 (3)
F1—C1—C2—C3124.4 (7)C20—C15—O3—C14108.2 (4)
F2'—C1—C2—C345.0 (11)C16—C15—O3—C1474.5 (4)
F3—C1—C2—C3122.2 (7)O5—C21—O4—C196.7 (6)
F1'—C1—C2—C362.1 (11)C22—C21—O4—C19173.5 (3)
C7—C2—C3—C41.3 (10)C18—C19—O4—C21119.5 (4)
C1—C2—C3—C4179.9 (6)C20—C19—O4—C2163.5 (5)
C2—C3—C4—C50.1 (8)C33—C28—C29—C300.0
C2—C3—C4—Cl1179.9 (5)O6—C28—C29—C30174.0 (17)
C3—C4—C5—O1179.1 (4)C33—C28—C29—Cl2174.4 (14)
Cl1—C4—C5—O10.9 (5)O6—C28—C29—Cl20.4 (15)
C3—C4—C5—C60.9 (7)C28—C29—C30—C310.0
Cl1—C4—C5—C6179.1 (3)Cl2—C29—C30—C31174.9 (13)
O1—C5—C6—C7179.8 (4)C29—C30—C31—C320.0
C4—C5—C6—C70.2 (6)C29—C30—C31—C34172 (2)
C5—C6—C7—C21.2 (8)C30—C31—C32—C330.0
C3—C2—C7—C62.0 (9)C34—C31—C32—C33172 (2)
C1—C2—C7—C6179.4 (6)C31—C32—C33—C280.0
C13—C8—C9—C100.4 (6)C29—C28—C33—C320.0
O1—C8—C9—C10175.6 (4)O6—C28—C33—C32173.7 (17)
C8—C9—C10—C111.6 (7)C32—C31—C34—F414.0 (17)
C9—C10—C11—C120.9 (7)C30—C31—C34—F4158.2 (12)
C10—C11—C12—C130.9 (6)C32—C31—C34—F5104.6 (14)
C10—C11—C12—C14179.2 (4)C30—C31—C34—F583.2 (15)
C9—C8—C13—C121.4 (6)C32—C31—C34—F6135.9 (12)
O1—C8—C13—C12177.4 (3)C30—C31—C34—F636.3 (18)
C11—C12—C13—C82.0 (6)C29—C28—O6—C2661.6 (15)
C14—C12—C13—C8179.6 (3)C33—C28—O6—C26124.6 (12)
C11—C12—C14—O2172.4 (4)C27—C26—O6—C2841.3 (13)
C13—C12—C14—O25.9 (6)C25—C26—O6—C28155.0 (10)
C11—C12—C14—O38.0 (5)O6'—C26—O6—C2873.7 (15)
C13—C12—C14—O3173.7 (3)O6'—C28'—C29'—C30'170.9 (14)
C20—C15—C16—C171.2 (6)C33'—C28'—C29'—C30'0.0
O3—C15—C16—C17178.3 (4)O6'—C28'—C29'—Cl2'8.6 (14)
C15—C16—C17—C180.1 (7)C33'—C28'—C29'—Cl2'179.5 (9)
C16—C17—C18—C190.9 (7)C28'—C29'—C30'—C31'0.0
C17—C18—C19—C200.4 (6)Cl2'—C29'—C30'—C31'179.4 (10)
C17—C18—C19—O4176.5 (4)C29'—C30'—C31'—C32'0.0
C16—C15—C20—C191.7 (5)C29'—C30'—C31'—C34'179.2 (15)
O3—C15—C20—C19178.9 (3)C30'—C31'—C32'—C33'0.0
C18—C19—C20—C150.8 (6)C34'—C31'—C32'—C33'179.2 (15)
O4—C19—C20—C15177.7 (3)C31'—C32'—C33'—C28'0.0
O5—C21—C22—C27174.1 (5)O6'—C28'—C33'—C32'172.2 (12)
O4—C21—C22—C275.7 (6)C29'—C28'—C33'—C32'0.0
O5—C21—C22—C235.6 (7)C32'—C31'—C34'—F5'10.0 (13)
O4—C21—C22—C23174.6 (4)C30'—C31'—C34'—F5'169.1 (9)
C27—C22—C23—C240.5 (9)C32'—C31'—C34'—F6'107.7 (10)
C21—C22—C23—C24179.8 (5)C30'—C31'—C34'—F6'73.1 (12)
C22—C23—C24—C251.8 (11)C32'—C31'—C34'—F4'132.7 (10)
C23—C24—C25—C260.9 (12)C30'—C31'—C34'—F4'46.5 (14)
C24—C25—C26—C271.4 (12)C29'—C28'—O6'—C2688.4 (16)
C24—C25—C26—O6'164.3 (9)C33'—C28'—O6'—C26100.1 (12)
C24—C25—C26—O6161.9 (8)C27—C26—O6'—C28'6.7 (19)
C25—C26—C27—C222.6 (10)C25—C26—O6'—C28'168.2 (11)
O6'—C26—C27—C22162.2 (9)O6—C26—O6'—C28'79.3 (16)
O6—C26—C27—C22160.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20···O1i0.932.503.412 (5)166
C10—H10···O2ii0.932.593.152 (5)120
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC34H18Cl2F6O6
Mr707.38
Crystal system, space groupTriclinic, P1
Temperature (K)292
a, b, c (Å)7.7175 (11), 8.7399 (12), 23.973 (3)
α, β, γ (°)92.986 (2), 98.485 (3), 92.611 (3)
V3)1594.8 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13550, 5564, 3199
Rint0.062
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.079, 0.257, 1.00
No. of reflections5564
No. of parameters528
No. of restraints215
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.51, 0.36

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20···O1i0.932.503.412 (5)166.4
C10—H10···O2ii0.932.593.152 (5)119.6
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y, z.
 

Acknowledgements

The authors gratefully acknowledge financial support of this work by the National Basic Research Program of China (grant No. 2010CB126100), the National Natural Science Foundation of China (grant Nos. 21172090 and 21002037). The research was supported in part by the PCSIRT (grant No. IRT0953).

References

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First citationBruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDayan, F. E. & Allen, S. N. (2000). Pest Manage. Sci. 56, 717–722.  Web of Science CrossRef CAS Google Scholar
First citationPeng, H. & He, H.-W. (2006). Acta Cryst. E62, o5371–o5372.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationPeng, H. & He, H. W. (2007). Chin. J. Org. Chem. 27, 502–506.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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