organic compounds
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
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). For the structures of related compounds, see: Peng & He (2006, 2007). For standard bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 2001); cell 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, 2009); software used to prepare material for publication: PLATON.
Supporting information
https://doi.org/10.1107/S1600536812030826/bg2468sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030826/bg2468Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812030826/bg2468Isup3.cml
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
(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.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
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.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
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 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?]
Data collection: SMART (Bruker, 2001); cell
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).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. |
C34H18Cl2F6O6 | Z = 2 |
Mr = 707.38 | F(000) = 716 |
Triclinic, P1 | Dx = 1.473 Mg m−3 |
a = 7.7175 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.7399 (12) Å | Cell parameters from 2828 reflections |
c = 23.973 (3) Å | θ = 2.3–23.0° |
α = 92.986 (2)° | µ = 0.28 mm−1 |
β = 98.485 (3)° | T = 292 K |
γ = 92.611 (3)° | Block, yellow |
V = 1594.8 (4) Å3 | 0.30 × 0.20 × 0.20 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3199 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
φ and ω scans | h = −9→9 |
13550 measured reflections | k = −10→10 |
5564 independent reflections | l = −25→28 |
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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.257 | H-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 parameters | Δρmax = 0.51 e Å−3 |
215 restraints | Δρmin = −0.36 e Å−3 |
C34H18Cl2F6O6 | γ = 92.611 (3)° |
Mr = 707.38 | V = 1594.8 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7175 (11) Å | Mo Kα radiation |
b = 8.7399 (12) Å | µ = 0.28 mm−1 |
c = 23.973 (3) Å | T = 292 K |
α = 92.986 (2)° | 0.30 × 0.20 × 0.20 mm |
β = 98.485 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 3199 reflections with I > 2σ(I) |
13550 measured reflections | Rint = 0.062 |
5564 independent reflections |
R[F2 > 2σ(F2)] = 0.079 | 215 restraints |
wR(F2) = 0.257 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.51 e Å−3 |
5564 reflections | Δρmin = −0.36 e Å−3 |
528 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 1.0008 (10) | 0.4068 (9) | 0.1855 (3) | 0.164 (4) | |
F1 | 1.1346 (11) | 0.3142 (8) | 0.1888 (3) | 0.173 (3) | 0.715 (11) |
F2 | 0.9704 (16) | 0.4550 (9) | 0.1344 (2) | 0.181 (4) | 0.715 (11) |
F3 | 0.8624 (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) |
C2 | 1.0228 (9) | 0.5297 (6) | 0.2317 (2) | 0.1074 (18) | |
C3 | 1.0153 (8) | 0.6824 (6) | 0.2186 (2) | 0.1061 (17) | |
H3 | 0.9965 | 0.7081 | 0.1811 | 0.127* | |
C4 | 1.0356 (6) | 0.7936 (5) | 0.26078 (19) | 0.0780 (12) | |
C5 | 1.0635 (5) | 0.7577 (4) | 0.31719 (16) | 0.0606 (9) | |
C6 | 1.0725 (6) | 0.6045 (5) | 0.32885 (18) | 0.0718 (11) | |
H6 | 1.0915 | 0.5779 | 0.3662 | 0.086* | |
C7 | 1.0540 (7) | 0.4930 (6) | 0.2868 (2) | 0.0921 (14) | |
H7 | 1.0627 | 0.3908 | 0.2955 | 0.111* | |
Cl1 | 1.0268 (2) | 0.98315 (14) | 0.24459 (6) | 0.1118 (6) | |
C8 | 1.0931 (5) | 0.8438 (4) | 0.41370 (16) | 0.0633 (10) | |
C9 | 1.2532 (5) | 0.8562 (5) | 0.44654 (19) | 0.0730 (11) | |
H9 | 1.3538 | 0.8795 | 0.4309 | 0.088* | |
C10 | 1.2640 (5) | 0.8340 (6) | 0.50298 (19) | 0.0803 (13) | |
H10 | 1.3727 | 0.8449 | 0.5258 | 0.096* | |
C11 | 1.1163 (5) | 0.7958 (5) | 0.52665 (17) | 0.0727 (12) | |
H11 | 1.1251 | 0.7795 | 0.5650 | 0.087* | |
C12 | 0.9547 (4) | 0.7821 (4) | 0.49233 (15) | 0.0568 (9) | |
C13 | 0.9418 (5) | 0.8086 (4) | 0.43542 (16) | 0.0583 (9) | |
H13 | 0.8333 | 0.8028 | 0.4124 | 0.070* | |
C14 | 0.7901 (5) | 0.7436 (4) | 0.51447 (16) | 0.0605 (10) | |
C15 | 0.6718 (5) | 0.6869 (4) | 0.59670 (15) | 0.0593 (9) | |
C16 | 0.5571 (6) | 0.5592 (5) | 0.58476 (17) | 0.0718 (11) | |
H16 | 0.5728 | 0.4834 | 0.5575 | 0.086* | |
C17 | 0.4200 (7) | 0.5491 (5) | 0.6147 (2) | 0.0841 (13) | |
H17 | 0.3414 | 0.4641 | 0.6074 | 0.101* | |
C18 | 0.3932 (6) | 0.6588 (5) | 0.65491 (18) | 0.0762 (12) | |
H18 | 0.2976 | 0.6493 | 0.6742 | 0.091* | |
C19 | 0.5100 (5) | 0.7820 (5) | 0.66599 (16) | 0.0659 (10) | |
C20 | 0.6535 (5) | 0.7982 (5) | 0.63710 (15) | 0.0629 (10) | |
H20 | 0.7338 | 0.8819 | 0.6451 | 0.075* | |
C21 | 0.4647 (5) | 1.0363 (5) | 0.69507 (19) | 0.0743 (12) | |
C22 | 0.4654 (6) | 1.1432 (5) | 0.74417 (19) | 0.0790 (12) | |
C23 | 0.4556 (8) | 1.2993 (6) | 0.7364 (2) | 0.1024 (16) | |
H23 | 0.4483 | 1.3340 | 0.7002 | 0.123* | |
C24 | 0.4564 (11) | 1.4006 (7) | 0.7804 (3) | 0.135 (2) | |
H24 | 0.4531 | 1.5047 | 0.7744 | 0.162* | |
C25 | 0.4619 (11) | 1.3539 (8) | 0.8330 (3) | 0.146 (3) | |
H25 | 0.4607 | 1.4248 | 0.8632 | 0.175* | |
C26 | 0.4692 (10) | 1.1990 (7) | 0.8417 (2) | 0.121 (2) | |
C27 | 0.4746 (7) | 1.0952 (6) | 0.7987 (2) | 0.0950 (15) | |
H27 | 0.4843 | 0.9919 | 0.8055 | 0.114* | |
O1 | 1.0799 (4) | 0.8770 (3) | 0.35637 (11) | 0.0716 (8) | |
O2 | 0.6463 (3) | 0.7448 (4) | 0.48806 (11) | 0.0797 (9) | |
O3 | 0.8193 (3) | 0.7046 (3) | 0.56895 (10) | 0.0678 (8) | |
O4 | 0.4900 (4) | 0.8907 (3) | 0.70907 (11) | 0.0729 (8) | |
O5 | 0.4436 (5) | 1.0719 (4) | 0.64716 (14) | 0.1047 (11) | |
C28 | 0.4973 (19) | 1.0073 (12) | 0.9132 (8) | 0.114 (8) | 0.429 (5) |
C29 | 0.6790 (19) | 1.0061 (12) | 0.9252 (7) | 0.092 (4) | 0.429 (5) |
C30 | 0.7572 (13) | 0.8795 (14) | 0.9487 (8) | 0.116 (6) | 0.429 (5) |
H30 | 0.8788 | 0.8787 | 0.9567 | 0.139* | 0.429 (5) |
C31 | 0.6537 (14) | 0.7541 (14) | 0.9603 (10) | 0.121 (3) | 0.429 (5) |
C32 | 0.4720 (14) | 0.7553 (15) | 0.9483 (10) | 0.146 (8) | 0.429 (5) |
H32 | 0.4028 | 0.6714 | 0.9560 | 0.175* | 0.429 (5) |
C33 | 0.3938 (14) | 0.8819 (16) | 0.9247 (8) | 0.160 (11) | 0.429 (5) |
H33 | 0.2722 | 0.8827 | 0.9167 | 0.192* | 0.429 (5) |
Cl2 | 0.8236 (8) | 1.1645 (6) | 0.9180 (2) | 0.171 (2) | 0.429 (5) |
C34 | 0.7402 (18) | 0.6295 (15) | 0.9921 (6) | 0.176 (4) | 0.429 (5) |
F4 | 0.6176 (18) | 0.5555 (19) | 1.0149 (8) | 0.252 (5) | 0.429 (5) |
F5 | 0.802 (2) | 0.5392 (18) | 0.9542 (6) | 0.200 (6) | 0.429 (5) |
F6 | 0.8722 (19) | 0.6868 (17) | 1.0316 (7) | 0.207 (7) | 0.429 (5) |
O6 | 0.4227 (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' | 0.4511 | 0.7148 | 0.9577 | 0.146* | 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' | 0.9370 | 0.8935 | 0.9523 | 0.207* | 0.571 (5) |
C33' | 0.7456 (15) | 1.0330 (12) | 0.9238 (7) | 0.153 (7) | 0.571 (5) |
H33' | 0.8194 | 1.1128 | 0.9153 | 0.184* | 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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.272 (12) | 0.130 (7) | 0.086 (5) | −0.012 (8) | 0.017 (6) | 0.017 (5) |
F1 | 0.256 (7) | 0.111 (5) | 0.157 (6) | 0.041 (5) | 0.058 (5) | −0.039 (4) |
F2 | 0.296 (10) | 0.152 (5) | 0.091 (4) | 0.017 (7) | 0.019 (5) | −0.012 (3) |
F3 | 0.235 (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) |
C2 | 0.184 (6) | 0.074 (3) | 0.061 (3) | 0.015 (3) | 0.005 (3) | −0.001 (2) |
C3 | 0.168 (5) | 0.090 (4) | 0.054 (3) | −0.003 (3) | 0.000 (3) | 0.010 (3) |
C4 | 0.094 (3) | 0.063 (2) | 0.072 (3) | −0.004 (2) | −0.005 (2) | 0.014 (2) |
C5 | 0.058 (2) | 0.065 (2) | 0.058 (2) | −0.0022 (17) | 0.0071 (17) | 0.0061 (19) |
C6 | 0.086 (3) | 0.072 (3) | 0.058 (2) | 0.013 (2) | 0.008 (2) | 0.012 (2) |
C7 | 0.130 (4) | 0.070 (3) | 0.078 (3) | 0.020 (3) | 0.013 (3) | 0.006 (2) |
Cl1 | 0.1702 (14) | 0.0692 (8) | 0.0854 (9) | −0.0165 (8) | −0.0159 (8) | 0.0242 (6) |
C8 | 0.068 (3) | 0.065 (2) | 0.058 (2) | 0.0083 (18) | 0.0104 (19) | 0.0010 (18) |
C9 | 0.052 (2) | 0.088 (3) | 0.081 (3) | 0.009 (2) | 0.014 (2) | 0.002 (2) |
C10 | 0.051 (2) | 0.117 (4) | 0.071 (3) | 0.014 (2) | 0.000 (2) | 0.002 (3) |
C11 | 0.055 (2) | 0.102 (3) | 0.061 (3) | 0.020 (2) | 0.0035 (19) | 0.001 (2) |
C12 | 0.051 (2) | 0.063 (2) | 0.054 (2) | 0.0072 (16) | 0.0043 (16) | −0.0042 (17) |
C13 | 0.053 (2) | 0.060 (2) | 0.059 (2) | 0.0023 (16) | 0.0006 (17) | −0.0021 (17) |
C14 | 0.055 (2) | 0.071 (2) | 0.054 (2) | 0.0106 (17) | 0.0024 (18) | −0.0021 (18) |
C15 | 0.062 (2) | 0.067 (2) | 0.049 (2) | 0.0043 (18) | 0.0061 (17) | 0.0102 (18) |
C16 | 0.086 (3) | 0.069 (3) | 0.057 (2) | −0.003 (2) | 0.003 (2) | 0.0038 (19) |
C17 | 0.098 (3) | 0.082 (3) | 0.068 (3) | −0.030 (3) | 0.006 (3) | 0.013 (2) |
C18 | 0.081 (3) | 0.083 (3) | 0.067 (3) | −0.014 (2) | 0.018 (2) | 0.021 (2) |
C19 | 0.076 (3) | 0.074 (3) | 0.048 (2) | 0.004 (2) | 0.0071 (19) | 0.0123 (19) |
C20 | 0.060 (2) | 0.071 (2) | 0.056 (2) | −0.0042 (18) | 0.0027 (18) | 0.012 (2) |
C21 | 0.073 (3) | 0.095 (3) | 0.060 (3) | 0.017 (2) | 0.012 (2) | 0.025 (2) |
C22 | 0.088 (3) | 0.083 (3) | 0.069 (3) | 0.018 (2) | 0.014 (2) | 0.013 (2) |
C23 | 0.140 (5) | 0.086 (4) | 0.084 (4) | 0.023 (3) | 0.017 (3) | 0.022 (3) |
C24 | 0.213 (8) | 0.079 (4) | 0.111 (5) | 0.031 (4) | 0.013 (5) | 0.010 (4) |
C25 | 0.225 (8) | 0.098 (5) | 0.106 (5) | 0.044 (5) | −0.009 (5) | −0.011 (4) |
C26 | 0.197 (7) | 0.100 (4) | 0.070 (4) | 0.055 (4) | 0.013 (4) | 0.011 (3) |
C27 | 0.144 (4) | 0.080 (3) | 0.067 (3) | 0.032 (3) | 0.022 (3) | 0.014 (2) |
O1 | 0.0889 (19) | 0.0666 (16) | 0.0598 (17) | −0.0009 (14) | 0.0135 (14) | 0.0058 (13) |
O2 | 0.0510 (16) | 0.125 (3) | 0.0620 (17) | 0.0010 (15) | 0.0011 (13) | 0.0167 (16) |
O3 | 0.0578 (15) | 0.0908 (19) | 0.0541 (16) | 0.0127 (13) | 0.0022 (12) | 0.0080 (13) |
O4 | 0.095 (2) | 0.0740 (18) | 0.0524 (16) | 0.0045 (15) | 0.0167 (13) | 0.0099 (14) |
O5 | 0.138 (3) | 0.116 (3) | 0.068 (2) | 0.047 (2) | 0.0216 (19) | 0.0280 (19) |
C28 | 0.176 (18) | 0.107 (16) | 0.063 (12) | −0.023 (16) | 0.049 (12) | −0.009 (11) |
C29 | 0.112 (13) | 0.085 (11) | 0.075 (10) | 0.002 (9) | 0.005 (9) | 0.001 (8) |
C30 | 0.097 (10) | 0.147 (18) | 0.096 (12) | 0.010 (11) | −0.001 (8) | −0.019 (12) |
C31 | 0.149 (7) | 0.126 (6) | 0.087 (4) | 0.041 (5) | 0.007 (5) | 0.011 (4) |
C32 | 0.177 (12) | 0.128 (11) | 0.134 (12) | −0.016 (9) | 0.035 (9) | 0.006 (9) |
C33 | 0.162 (14) | 0.169 (14) | 0.153 (14) | 0.030 (10) | 0.031 (10) | −0.001 (10) |
Cl2 | 0.192 (5) | 0.132 (4) | 0.175 (5) | −0.039 (3) | −0.012 (4) | 0.035 (3) |
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 | 0.231 (11) | 0.154 (8) | 0.217 (10) | 0.085 (8) | 0.024 (8) | 0.002 (7) |
F6 | 0.190 (10) | 0.225 (11) | 0.214 (11) | 0.042 (8) | 0.035 (8) | 0.062 (9) |
O6 | 0.102 (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) |
C1—F2 | 1.307 (7) | C21—O4 | 1.348 (5) |
C1—F3' | 1.312 (8) | C21—C22 | 1.464 (6) |
C1—F1 | 1.337 (7) | C22—C27 | 1.387 (6) |
C1—F2' | 1.367 (8) | C22—C23 | 1.391 (7) |
C1—F3 | 1.372 (7) | C23—C24 | 1.340 (8) |
C1—F1' | 1.394 (9) | C23—H23 | 0.9300 |
C1—C2 | 1.487 (8) | C24—C25 | 1.340 (9) |
C2—C7 | 1.366 (7) | C24—H24 | 0.9300 |
C2—C3 | 1.389 (7) | C25—C26 | 1.383 (8) |
C3—C4 | 1.353 (6) | C25—H25 | 0.9300 |
C3—H3 | 0.9300 | C26—C27 | 1.344 (7) |
C4—C5 | 1.392 (6) | C26—O6' | 1.418 (9) |
C4—Cl1 | 1.723 (4) | C26—O6 | 1.444 (9) |
C5—O1 | 1.355 (5) | C27—H27 | 0.9300 |
C5—C6 | 1.385 (6) | C28—C29 | 1.3900 |
C6—C7 | 1.352 (6) | C28—C33 | 1.3900 |
C6—H6 | 0.9300 | C28—O6 | 1.442 (12) |
C7—H7 | 0.9300 | C29—C30 | 1.3900 |
C8—C9 | 1.360 (6) | C29—Cl2 | 1.770 (9) |
C8—C13 | 1.376 (5) | C30—C31 | 1.3900 |
C8—O1 | 1.409 (5) | C30—H30 | 0.9300 |
C9—C10 | 1.368 (6) | C31—C32 | 1.3900 |
C9—H9 | 0.9300 | C31—C34 | 1.489 (11) |
C10—C11 | 1.382 (6) | C32—C33 | 1.3900 |
C10—H10 | 0.9300 | C32—H32 | 0.9300 |
C11—C12 | 1.385 (5) | C33—H33 | 0.9300 |
C11—H11 | 0.9300 | C34—F4 | 1.321 (9) |
C12—C13 | 1.386 (5) | C34—F5 | 1.330 (9) |
C12—C14 | 1.479 (5) | C34—F6 | 1.343 (9) |
C13—H13 | 0.9300 | C28'—O6' | 1.295 (13) |
C14—O2 | 1.195 (4) | C28'—C29' | 1.3900 |
C14—O3 | 1.356 (4) | C28'—C33' | 1.3900 |
C15—C20 | 1.363 (5) | C29'—C30' | 1.3900 |
C15—C16 | 1.384 (6) | C29'—Cl2' | 1.673 (7) |
C15—O3 | 1.407 (4) | C30'—C31' | 1.3900 |
C16—C17 | 1.365 (6) | C30'—H30' | 0.9300 |
C16—H16 | 0.9300 | C31'—C32' | 1.3900 |
C17—C18 | 1.368 (6) | C31'—C34' | 1.517 (10) |
C17—H17 | 0.9300 | C32'—C33' | 1.3900 |
C18—C19 | 1.362 (6) | C32'—H32' | 0.9300 |
C18—H18 | 0.9300 | C33'—H33' | 0.9300 |
C19—C20 | 1.396 (5) | C34'—F5' | 1.327 (8) |
C19—O4 | 1.397 (5) | C34'—F6' | 1.341 (8) |
C20—H20 | 0.9300 | C34'—F4' | 1.351 (9) |
C21—O5 | 1.196 (5) | ||
F2—C1—F3' | 117.4 (12) | O5—C21—O4 | 122.5 (4) |
F2—C1—F1 | 109.1 (6) | O5—C21—C22 | 124.4 (4) |
F3'—C1—F1 | 51.7 (8) | O4—C21—C22 | 113.1 (4) |
F2—C1—F2' | 39.9 (6) | C27—C22—C23 | 118.1 (4) |
F3'—C1—F2' | 106.4 (8) | C27—C22—C21 | 122.6 (4) |
F1—C1—F2' | 135.0 (10) | C23—C22—C21 | 119.4 (4) |
F2—C1—F3 | 107.1 (7) | C24—C23—C22 | 121.0 (5) |
F3'—C1—F3 | 50.8 (8) | C24—C23—H23 | 119.5 |
F1—C1—F3 | 102.4 (6) | C22—C23—H23 | 119.5 |
F2'—C1—F3 | 71.8 (7) | C23—C24—C25 | 120.9 (6) |
F2—C1—F1' | 60.3 (7) | C23—C24—H24 | 119.5 |
F3'—C1—F1' | 103.6 (8) | C25—C24—H24 | 119.5 |
F1—C1—F1' | 59.1 (8) | C24—C25—C26 | 119.2 (6) |
F2'—C1—F1' | 100.0 (7) | C24—C25—H25 | 120.4 |
F3—C1—F1' | 145.4 (9) | C26—C25—H25 | 120.4 |
F2—C1—C2 | 115.0 (6) | C27—C26—C25 | 121.2 (6) |
F3'—C1—C2 | 127.5 (11) | C27—C26—O6' | 127.3 (7) |
F1—C1—C2 | 113.1 (6) | C25—C26—O6' | 108.8 (7) |
F2'—C1—C2 | 110.7 (9) | C27—C26—O6 | 118.9 (7) |
F3—C1—C2 | 109.3 (6) | C25—C26—O6 | 117.8 (6) |
F1'—C1—C2 | 105.1 (9) | O6'—C26—O6 | 32.3 (6) |
C7—C2—C3 | 120.0 (4) | C26—C27—C22 | 119.5 (5) |
C7—C2—C1 | 120.2 (5) | C26—C27—H27 | 120.2 |
C3—C2—C1 | 119.8 (5) | C22—C27—H27 | 120.2 |
C4—C3—C2 | 119.5 (4) | C5—O1—C8 | 118.1 (3) |
C4—C3—H3 | 120.3 | C14—O3—C15 | 117.1 (3) |
C2—C3—H3 | 120.3 | C21—O4—C19 | 117.9 (3) |
C3—C4—C5 | 121.2 (4) | C29—C28—C33 | 120.0 |
C3—C4—Cl1 | 119.5 (4) | C29—C28—O6 | 117.6 (10) |
C5—C4—Cl1 | 119.3 (3) | C33—C28—O6 | 122.1 (10) |
O1—C5—C6 | 125.3 (4) | C28—C29—C30 | 120.0 |
O1—C5—C4 | 116.8 (4) | C28—C29—Cl2 | 124.1 (8) |
C6—C5—C4 | 117.9 (4) | C30—C29—Cl2 | 115.6 (8) |
C7—C6—C5 | 121.1 (4) | C29—C30—C31 | 120.0 |
C7—C6—H6 | 119.4 | C29—C30—H30 | 120.0 |
C5—C6—H6 | 119.4 | C31—C30—H30 | 120.0 |
C6—C7—C2 | 120.2 (4) | C32—C31—C30 | 120.0 |
C6—C7—H7 | 119.9 | C32—C31—C34 | 121.0 (5) |
C2—C7—H7 | 119.9 | C30—C31—C34 | 118.5 (5) |
C9—C8—C13 | 122.0 (4) | C33—C32—C31 | 120.0 |
C9—C8—O1 | 119.2 (4) | C33—C32—H32 | 120.0 |
C13—C8—O1 | 118.7 (3) | C31—C32—H32 | 120.0 |
C8—C9—C10 | 119.0 (4) | C32—C33—C28 | 120.0 |
C8—C9—H9 | 120.5 | C32—C33—H33 | 120.0 |
C10—C9—H9 | 120.5 | C28—C33—H33 | 120.0 |
C9—C10—C11 | 121.2 (4) | F4—C34—F5 | 111.1 (9) |
C9—C10—H10 | 119.4 | F4—C34—F6 | 111.5 (9) |
C11—C10—H10 | 119.4 | F5—C34—F6 | 110.0 (8) |
C10—C11—C12 | 118.9 (4) | F4—C34—C31 | 106.9 (11) |
C10—C11—H11 | 120.6 | F5—C34—C31 | 106.0 (13) |
C12—C11—H11 | 120.6 | F6—C34—C31 | 111.1 (13) |
C11—C12—C13 | 120.3 (4) | C28—O6—C26 | 116.3 (10) |
C11—C12—C14 | 122.3 (4) | O6'—C28'—C29' | 127.3 (11) |
C13—C12—C14 | 117.4 (3) | O6'—C28'—C33' | 112.2 (11) |
C8—C13—C12 | 118.5 (3) | C29'—C28'—C33' | 120.0 |
C8—C13—H13 | 120.7 | C28'—C29'—C30' | 120.0 |
C12—C13—H13 | 120.7 | C28'—C29'—Cl2' | 115.6 (8) |
O2—C14—O3 | 122.7 (4) | C30'—C29'—Cl2' | 124.4 (8) |
O2—C14—C12 | 124.9 (4) | C29'—C30'—C31' | 120.0 |
O3—C14—C12 | 112.4 (3) | C29'—C30'—H30' | 120.0 |
C20—C15—C16 | 122.6 (4) | C31'—C30'—H30' | 120.0 |
C20—C15—O3 | 116.5 (3) | C32'—C31'—C30' | 120.0 |
C16—C15—O3 | 120.9 (3) | C32'—C31'—C34' | 121.0 (4) |
C17—C16—C15 | 117.1 (4) | C30'—C31'—C34' | 119.0 (4) |
C17—C16—H16 | 121.4 | C33'—C32'—C31' | 120.0 |
C15—C16—H16 | 121.4 | C33'—C32'—H32' | 120.0 |
C16—C17—C18 | 122.8 (4) | C31'—C32'—H32' | 120.0 |
C16—C17—H17 | 118.6 | C32'—C33'—C28' | 120.0 |
C18—C17—H17 | 118.6 | C32'—C33'—H33' | 120.0 |
C19—C18—C17 | 118.4 (4) | C28'—C33'—H33' | 120.0 |
C19—C18—H18 | 120.8 | F5'—C34'—F6' | 108.8 (8) |
C17—C18—H18 | 120.8 | F5'—C34'—F4' | 112.4 (8) |
C18—C19—C20 | 121.5 (4) | F6'—C34'—F4' | 106.6 (8) |
C18—C19—O4 | 119.1 (4) | F5'—C34'—C31' | 105.2 (7) |
C20—C19—O4 | 119.4 (4) | F6'—C34'—C31' | 111.3 (10) |
C15—C20—C19 | 117.6 (4) | F4'—C34'—C31' | 112.4 (12) |
C15—C20—H20 | 121.2 | C28'—O6'—C26 | 116.6 (10) |
C19—C20—H20 | 121.2 | ||
F2—C1—C2—C7 | 179.6 (8) | C23—C22—C27—C26 | 1.7 (8) |
F3'—C1—C2—C7 | 4.4 (15) | C21—C22—C27—C26 | −178.0 (5) |
F1—C1—C2—C7 | −54.1 (9) | C6—C5—O1—C8 | −5.4 (5) |
F2'—C1—C2—C7 | 136.4 (9) | C4—C5—O1—C8 | 174.6 (3) |
F3—C1—C2—C7 | 59.2 (8) | C9—C8—O1—C5 | 101.9 (4) |
F1'—C1—C2—C7 | −116.5 (11) | C13—C8—O1—C5 | −81.9 (4) |
F2—C1—C2—C3 | −1.8 (11) | O2—C14—O3—C15 | −9.2 (5) |
F3'—C1—C2—C3 | −177.0 (13) | C12—C14—O3—C15 | 171.2 (3) |
F1—C1—C2—C3 | 124.4 (7) | C20—C15—O3—C14 | −108.2 (4) |
F2'—C1—C2—C3 | −45.0 (11) | C16—C15—O3—C14 | 74.5 (4) |
F3—C1—C2—C3 | −122.2 (7) | O5—C21—O4—C19 | 6.7 (6) |
F1'—C1—C2—C3 | 62.1 (11) | C22—C21—O4—C19 | −173.5 (3) |
C7—C2—C3—C4 | −1.3 (10) | C18—C19—O4—C21 | −119.5 (4) |
C1—C2—C3—C4 | −179.9 (6) | C20—C19—O4—C21 | 63.5 (5) |
C2—C3—C4—C5 | −0.1 (8) | C33—C28—C29—C30 | 0.0 |
C2—C3—C4—Cl1 | 179.9 (5) | O6—C28—C29—C30 | 174.0 (17) |
C3—C4—C5—O1 | −179.1 (4) | C33—C28—C29—Cl2 | −174.4 (14) |
Cl1—C4—C5—O1 | 0.9 (5) | O6—C28—C29—Cl2 | −0.4 (15) |
C3—C4—C5—C6 | 0.9 (7) | C28—C29—C30—C31 | 0.0 |
Cl1—C4—C5—C6 | −179.1 (3) | Cl2—C29—C30—C31 | 174.9 (13) |
O1—C5—C6—C7 | 179.8 (4) | C29—C30—C31—C32 | 0.0 |
C4—C5—C6—C7 | −0.2 (6) | C29—C30—C31—C34 | −172 (2) |
C5—C6—C7—C2 | −1.2 (8) | C30—C31—C32—C33 | 0.0 |
C3—C2—C7—C6 | 2.0 (9) | C34—C31—C32—C33 | 172 (2) |
C1—C2—C7—C6 | −179.4 (6) | C31—C32—C33—C28 | 0.0 |
C13—C8—C9—C10 | −0.4 (6) | C29—C28—C33—C32 | 0.0 |
O1—C8—C9—C10 | 175.6 (4) | O6—C28—C33—C32 | −173.7 (17) |
C8—C9—C10—C11 | 1.6 (7) | C32—C31—C34—F4 | −14.0 (17) |
C9—C10—C11—C12 | −0.9 (7) | C30—C31—C34—F4 | 158.2 (12) |
C10—C11—C12—C13 | −0.9 (6) | C32—C31—C34—F5 | 104.6 (14) |
C10—C11—C12—C14 | −179.2 (4) | C30—C31—C34—F5 | −83.2 (15) |
C9—C8—C13—C12 | −1.4 (6) | C32—C31—C34—F6 | −135.9 (12) |
O1—C8—C13—C12 | −177.4 (3) | C30—C31—C34—F6 | 36.3 (18) |
C11—C12—C13—C8 | 2.0 (6) | C29—C28—O6—C26 | 61.6 (15) |
C14—C12—C13—C8 | −179.6 (3) | C33—C28—O6—C26 | −124.6 (12) |
C11—C12—C14—O2 | 172.4 (4) | C27—C26—O6—C28 | 41.3 (13) |
C13—C12—C14—O2 | −5.9 (6) | C25—C26—O6—C28 | −155.0 (10) |
C11—C12—C14—O3 | −8.0 (5) | O6'—C26—O6—C28 | −73.7 (15) |
C13—C12—C14—O3 | 173.7 (3) | O6'—C28'—C29'—C30' | −170.9 (14) |
C20—C15—C16—C17 | 1.2 (6) | C33'—C28'—C29'—C30' | 0.0 |
O3—C15—C16—C17 | 178.3 (4) | O6'—C28'—C29'—Cl2' | 8.6 (14) |
C15—C16—C17—C18 | 0.1 (7) | C33'—C28'—C29'—Cl2' | 179.5 (9) |
C16—C17—C18—C19 | −0.9 (7) | C28'—C29'—C30'—C31' | 0.0 |
C17—C18—C19—C20 | 0.4 (6) | Cl2'—C29'—C30'—C31' | −179.4 (10) |
C17—C18—C19—O4 | −176.5 (4) | C29'—C30'—C31'—C32' | 0.0 |
C16—C15—C20—C19 | −1.7 (5) | C29'—C30'—C31'—C34' | −179.2 (15) |
O3—C15—C20—C19 | −178.9 (3) | C30'—C31'—C32'—C33' | 0.0 |
C18—C19—C20—C15 | 0.8 (6) | C34'—C31'—C32'—C33' | 179.2 (15) |
O4—C19—C20—C15 | 177.7 (3) | C31'—C32'—C33'—C28' | 0.0 |
O5—C21—C22—C27 | 174.1 (5) | O6'—C28'—C33'—C32' | 172.2 (12) |
O4—C21—C22—C27 | −5.7 (6) | C29'—C28'—C33'—C32' | 0.0 |
O5—C21—C22—C23 | −5.6 (7) | C32'—C31'—C34'—F5' | −10.0 (13) |
O4—C21—C22—C23 | 174.6 (4) | C30'—C31'—C34'—F5' | 169.1 (9) |
C27—C22—C23—C24 | 0.5 (9) | C32'—C31'—C34'—F6' | 107.7 (10) |
C21—C22—C23—C24 | −179.8 (5) | C30'—C31'—C34'—F6' | −73.1 (12) |
C22—C23—C24—C25 | −1.8 (11) | C32'—C31'—C34'—F4' | −132.7 (10) |
C23—C24—C25—C26 | 0.9 (12) | C30'—C31'—C34'—F4' | 46.5 (14) |
C24—C25—C26—C27 | 1.4 (12) | C29'—C28'—O6'—C26 | −88.4 (16) |
C24—C25—C26—O6' | 164.3 (9) | C33'—C28'—O6'—C26 | 100.1 (12) |
C24—C25—C26—O6 | −161.9 (8) | C27—C26—O6'—C28' | −6.7 (19) |
C25—C26—C27—C22 | −2.6 (10) | C25—C26—O6'—C28' | −168.2 (11) |
O6'—C26—C27—C22 | −162.2 (9) | O6—C26—O6'—C28' | 79.3 (16) |
O6—C26—C27—C22 | 160.4 (6) |
D—H···A | D—H | H···A | D···A | 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. |
Experimental details
Crystal data | |
Chemical formula | C34H18Cl2F6O6 |
Mr | 707.38 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1594.8 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13550, 5564, 3199 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.079, 0.257, 1.00 |
No. of reflections | 5564 |
No. of parameters | 528 |
No. of restraints | 215 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.51, −0.36 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20···O1i | 0.93 | 2.50 | 3.412 (5) | 166.4 |
C10—H10···O2ii | 0.93 | 2.59 | 3.152 (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
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. CSD CrossRef Web of Science Google Scholar
Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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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).