Acta Cryst. (2008). E64, o1756 [ doi:10.1107/S1600536808025506 ]
In the molecule of the title compound, C17H8Cl2F8N2O3, the two aromatic rings are oriented at a dihedral angle of 50.12 (3)°. Intramolecular N-H
O, C-HO and N-HCl hydrogen bonds result in the formation of two six- and one five-membered rings. The six-membered rings have flattened-boat conformations, while the five-membered ring adopts an envelope conformation. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules into centrosymmetric dimers.
The title compound was prepared according to the literature method (Drabek & Boeger, 1986). The crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.3 g) in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 8 d.
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 and 0.98 Å for aromatic and methine H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,N).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./hk2510fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. |
![[Figure 2]](./hk2510fig2thm.gif)
| Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. |
| C17H8Cl2F8N2O3 | F000 = 1016 |
| Mr = 511.15 | Dx = 1.683 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 25 reflections |
| a = 9.2300 (18) Å | θ = 9–12º |
| b = 16.404 (3) Å | µ = 0.42 mm−1 |
| c = 14.074 (3) Å | T = 294 (2) K |
| β = 108.77 (3)º | Block, colorless |
| V = 2017.6 (8) Å3 | 0.40 × 0.30 × 0.20 mm |
| Z = 4 |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.0000 |
| Radiation source: fine-focus sealed tube | θmax = 25.2º |
| Monochromator: graphite | θmin = 2.0º |
| T = 294(2) K | h = −11→10 |
| ω/2θ scans | k = 0→19 |
| Absorption correction: ψ scan (North et al., 1968) | l = 0→16 |
| Tmin = 0.851, Tmax = 0.921 | 3 standard reflections |
| 3609 measured reflections | every 200 reflections |
| 3609 independent reflections | intensity decay: none |
| 1922 reflections with I > 2σ(I) |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.086 | H-atom parameters constrained |
| wR(F2) = 0.248 | w = 1/[σ2(Fo2) + (0.1258P)2 + 1.1819P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max = 0.001 |
| 3609 reflections | Δρmax = 0.42 e Å−3 |
| 283 parameters | Δρmin = −0.34 e Å−3 |
| 96 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C17H8Cl2F8N2O3 | V = 2017.6 (8) Å3 |
| Mr = 511.15 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 9.2300 (18) Å | µ = 0.42 mm−1 |
| b = 16.404 (3) Å | T = 294 (2) K |
| c = 14.074 (3) Å | 0.40 × 0.30 × 0.20 mm |
| β = 108.77 (3)º |
| Enraf–Nonius CAD-4 diffractometer | 1922 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.0000 |
| Tmin = 0.851, Tmax = 0.921 | 3 standard reflections |
| 3609 measured reflections | every 200 reflections |
| 3609 independent reflections | intensity decay: none |
| R[F2 > 2σ(F2)] = 0.086 | 96 restraints |
| wR(F2) = 0.248 | H-atom parameters constrained |
| S = 1.09 | Δρmax = 0.42 e Å−3 |
| 3609 reflections | Δρmin = −0.34 e Å−3 |
| 283 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 > 2sigma(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 | ||
| Cl1 | 1.21022 (15) | 1.15534 (9) | 0.61828 (12) | 0.0527 (5) | |
| Cl2 | 1.06547 (19) | 0.83402 (11) | 0.80001 (17) | 0.0914 (8) | |
| F1 | 0.4001 (5) | 0.7889 (3) | 0.7184 (3) | 0.0975 (16) | |
| F2 | 0.4224 (4) | 0.8023 (3) | 0.3906 (3) | 0.0810 (13) | |
| F3 | 1.5260 (5) | 1.0359 (3) | 0.6887 (5) | 0.1116 (18) | |
| F4 | 1.5722 (4) | 0.9618 (3) | 0.8001 (4) | 0.1039 (17) | |
| F5 | 1.8146 (6) | 1.0579 (3) | 0.7942 (5) | 0.145 (3) | |
| F6 | 1.8127 (6) | 1.0156 (3) | 0.9703 (4) | 0.1121 (18) | |
| F7 | 1.9281 (6) | 1.1152 (3) | 0.9350 (4) | 0.119 (2) | |
| F8 | 1.6616 (6) | 1.1347 (3) | 0.9601 (4) | 0.1029 (15) | |
| O1 | 0.6850 (4) | 0.7921 (2) | 0.6546 (4) | 0.0703 (15) | |
| O2 | 0.6981 (4) | 1.0216 (3) | 0.5376 (3) | 0.0505 (11) | |
| O3 | 1.4248 (4) | 1.0694 (3) | 0.7916 (4) | 0.0758 (16) | |
| N1 | 0.5870 (4) | 0.9045 (2) | 0.5577 (3) | 0.0359 (11) | |
| H1A | 0.5033 | 0.9242 | 0.5175 | 0.043* | |
| N2 | 0.8483 (4) | 0.9219 (2) | 0.6377 (3) | 0.0327 (10) | |
| H2A | 0.8468 | 0.8724 | 0.6576 | 0.039* | |
| C1 | 0.1954 (8) | 0.7296 (5) | 0.5816 (6) | 0.074 (2) | |
| H1B | 0.1414 | 0.7140 | 0.6242 | 0.089* | |
| C2 | 0.1405 (7) | 0.7183 (4) | 0.4832 (5) | 0.0588 (17) | |
| H2B | 0.0444 | 0.6945 | 0.4569 | 0.071* | |
| C3 | 0.2142 (7) | 0.7389 (4) | 0.4199 (5) | 0.0607 (17) | |
| H3A | 0.1704 | 0.7275 | 0.3519 | 0.073* | |
| C4 | 0.3505 (6) | 0.7758 (4) | 0.4526 (4) | 0.0450 (14) | |
| C5 | 0.4228 (6) | 0.7893 (3) | 0.5551 (4) | 0.0435 (14) | |
| C6 | 0.3397 (7) | 0.7666 (4) | 0.6175 (5) | 0.0568 (16) | |
| C7 | 0.5790 (6) | 0.8247 (3) | 0.5960 (4) | 0.0437 (14) | |
| C8 | 0.7151 (6) | 0.9534 (3) | 0.5785 (4) | 0.0407 (14) | |
| C9 | 0.9852 (5) | 0.9614 (3) | 0.6689 (4) | 0.0330 (12) | |
| C10 | 1.0214 (5) | 1.0332 (3) | 0.6291 (4) | 0.0368 (12) | |
| H10A | 0.9477 | 1.0595 | 0.5770 | 0.044* | |
| C11 | 1.1661 (5) | 1.0655 (3) | 0.6667 (4) | 0.0355 (12) | |
| C12 | 1.2807 (6) | 1.0310 (4) | 0.7494 (5) | 0.0518 (16) | |
| C13 | 1.2445 (7) | 0.9591 (4) | 0.7901 (5) | 0.0572 (17) | |
| H13A | 1.3159 | 0.9350 | 0.8453 | 0.069* | |
| C14 | 1.1065 (5) | 0.9252 (3) | 0.7492 (4) | 0.0391 (13) | |
| C15 | 1.5460 (7) | 1.0386 (4) | 0.8024 (7) | 0.079 (3) | |
| C16 | 1.6854 (8) | 1.0845 (5) | 0.8271 (9) | 0.107 (4) | |
| H16A | 1.6576 | 1.1394 | 0.7999 | 0.129* | |
| C17 | 1.7772 (11) | 1.0946 (6) | 0.9319 (7) | 0.089 |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0401 (8) | 0.0436 (9) | 0.0782 (11) | −0.0152 (6) | 0.0242 (7) | −0.0007 (7) |
| Cl2 | 0.0513 (10) | 0.0599 (12) | 0.1330 (18) | −0.0100 (8) | −0.0123 (10) | 0.0497 (12) |
| F1 | 0.097 (3) | 0.135 (4) | 0.051 (3) | −0.054 (3) | 0.010 (2) | 0.026 (2) |
| F2 | 0.086 (3) | 0.103 (3) | 0.059 (3) | −0.045 (3) | 0.030 (2) | −0.034 (2) |
| F3 | 0.099 (4) | 0.106 (4) | 0.133 (5) | −0.034 (3) | 0.041 (3) | −0.032 (3) |
| F4 | 0.054 (2) | 0.072 (3) | 0.172 (5) | −0.010 (2) | 0.019 (3) | −0.015 (3) |
| F5 | 0.092 (3) | 0.141 (5) | 0.225 (7) | −0.023 (3) | 0.082 (4) | −0.111 (5) |
| F6 | 0.127 (4) | 0.104 (4) | 0.095 (4) | −0.017 (3) | 0.021 (3) | 0.052 (3) |
| F7 | 0.099 (3) | 0.083 (3) | 0.116 (4) | −0.024 (3) | −0.048 (3) | 0.006 (3) |
| F8 | 0.097 (3) | 0.111 (4) | 0.103 (4) | −0.001 (3) | 0.034 (3) | −0.012 (3) |
| O1 | 0.029 (2) | 0.047 (3) | 0.107 (4) | 0.0006 (18) | −0.017 (2) | 0.037 (2) |
| O2 | 0.046 (2) | 0.047 (3) | 0.057 (3) | −0.0033 (19) | 0.013 (2) | −0.005 (2) |
| O3 | 0.035 (2) | 0.043 (3) | 0.129 (5) | −0.009 (2) | −0.001 (2) | 0.009 (3) |
| N1 | 0.028 (2) | 0.019 (2) | 0.058 (3) | 0.0007 (17) | 0.009 (2) | 0.0093 (19) |
| N2 | 0.028 (2) | 0.025 (2) | 0.043 (3) | −0.0005 (17) | 0.0085 (19) | −0.0044 (19) |
| C1 | 0.070 (4) | 0.082 (5) | 0.076 (4) | −0.028 (4) | 0.032 (4) | 0.017 (4) |
| C2 | 0.046 (3) | 0.051 (4) | 0.071 (4) | −0.016 (3) | 0.007 (3) | 0.003 (3) |
| C3 | 0.059 (4) | 0.061 (4) | 0.051 (4) | −0.023 (3) | 0.002 (3) | −0.014 (3) |
| C4 | 0.045 (3) | 0.046 (3) | 0.042 (3) | −0.003 (3) | 0.011 (3) | −0.004 (3) |
| C5 | 0.039 (3) | 0.042 (3) | 0.047 (3) | −0.006 (2) | 0.011 (2) | 0.010 (3) |
| C6 | 0.044 (3) | 0.067 (4) | 0.053 (4) | −0.009 (3) | 0.007 (3) | 0.014 (3) |
| C7 | 0.045 (3) | 0.039 (3) | 0.047 (4) | −0.010 (3) | 0.016 (3) | 0.004 (3) |
| C8 | 0.037 (3) | 0.027 (3) | 0.051 (4) | 0.000 (2) | 0.005 (3) | 0.009 (3) |
| C9 | 0.026 (2) | 0.036 (3) | 0.036 (3) | 0.000 (2) | 0.009 (2) | −0.005 (2) |
| C10 | 0.032 (2) | 0.040 (3) | 0.042 (3) | −0.007 (2) | 0.016 (2) | −0.003 (2) |
| C11 | 0.033 (3) | 0.035 (3) | 0.044 (3) | −0.009 (2) | 0.020 (2) | 0.008 (2) |
| C12 | 0.030 (3) | 0.053 (4) | 0.065 (4) | −0.003 (2) | 0.006 (3) | 0.004 (3) |
| C13 | 0.042 (3) | 0.051 (4) | 0.071 (4) | 0.013 (3) | 0.007 (3) | 0.017 (3) |
| C14 | 0.022 (2) | 0.042 (3) | 0.049 (3) | 0.012 (2) | 0.005 (2) | 0.009 (2) |
| C15 | 0.029 (3) | 0.050 (5) | 0.142 (8) | 0.006 (3) | 0.007 (4) | −0.014 (4) |
| C16 | 0.041 (4) | 0.046 (4) | 0.219 (11) | −0.009 (3) | 0.021 (5) | 0.007 (6) |
| C17 | 0.080 | 0.089 | 0.096 | −0.006 | 0.026 | 0.004 |
| Cl1—C11 | 1.727 (5) | C2—C3 | 1.326 (9) |
| Cl2—C14 | 1.751 (6) | C2—H2B | 0.9300 |
| F1—C6 | 1.398 (7) | O3—C15 | 1.191 (7) |
| F2—C4 | 1.327 (7) | O3—C12 | 1.418 (6) |
| F3—C15 | 1.552 (10) | C3—C4 | 1.338 (8) |
| F4—C15 | 1.284 (8) | C3—H3A | 0.9300 |
| F5—C16 | 1.477 (9) | C4—C5 | 1.399 (8) |
| F6—C17 | 1.403 (10) | C5—C6 | 1.389 (8) |
| F7—C17 | 1.420 (10) | C5—C7 | 1.488 (7) |
| F8—C17 | 1.415 (10) | C9—C10 | 1.390 (7) |
| O1—C7 | 1.186 (6) | C9—C14 | 1.439 (7) |
| N1—C8 | 1.380 (6) | C10—C11 | 1.374 (7) |
| N1—C7 | 1.427 (7) | C10—H10A | 0.9300 |
| N1—H1A | 0.8600 | C11—C12 | 1.414 (7) |
| C1—C2 | 1.327 (10) | C12—C13 | 1.398 (8) |
| C1—C6 | 1.401 (9) | C13—C14 | 1.338 (8) |
| C1—H1B | 0.9300 | C13—H13A | 0.9300 |
| N2—C8 | 1.347 (6) | C15—C16 | 1.434 (9) |
| N2—C9 | 1.361 (6) | C16—C17 | 1.455 (13) |
| N2—H2A | 0.8600 | C16—H16A | 0.9800 |
| O2—C8 | 1.245 (6) | ||
| C8—N1—C7 | 126.7 (4) | C11—C10—C9 | 120.1 (5) |
| C8—N1—H1A | 116.6 | C11—C10—H10A | 120.0 |
| C7—N1—H1A | 116.6 | C9—C10—H10A | 120.0 |
| C2—C1—C6 | 115.8 (6) | C10—C11—C12 | 122.7 (5) |
| C2—C1—H1B | 122.1 | C10—C11—Cl1 | 120.0 (4) |
| C6—C1—H1B | 122.1 | C12—C11—Cl1 | 117.2 (4) |
| C8—N2—C9 | 125.8 (4) | C13—C12—C11 | 117.4 (5) |
| C8—N2—H2A | 117.1 | C13—C12—O3 | 121.2 (5) |
| C9—N2—H2A | 117.1 | C11—C12—O3 | 121.4 (5) |
| C1—C2—C3 | 124.0 (6) | C14—C13—C12 | 119.7 (5) |
| C1—C2—H2B | 118.0 | C14—C13—H13A | 120.2 |
| C3—C2—H2B | 118.0 | C12—C13—H13A | 120.2 |
| C15—O3—C12 | 125.5 (6) | C13—C14—C9 | 123.9 (5) |
| C2—C3—C4 | 120.9 (6) | C13—C14—Cl2 | 118.8 (4) |
| C2—C3—H3A | 119.6 | C9—C14—Cl2 | 117.2 (4) |
| C4—C3—H3A | 119.6 | O3—C15—F4 | 126.1 (6) |
| F2—C4—C3 | 122.4 (6) | O3—C15—C16 | 122.7 (7) |
| F2—C4—C5 | 117.0 (5) | F4—C15—C16 | 111.1 (6) |
| C3—C4—C5 | 120.7 (6) | O3—C15—F3 | 94.9 (6) |
| C6—C5—C4 | 115.6 (5) | F4—C15—F3 | 84.7 (6) |
| C6—C5—C7 | 121.6 (5) | C16—C15—F3 | 93.7 (7) |
| C4—C5—C7 | 122.8 (5) | C15—C16—C17 | 119.4 (9) |
| C5—C6—F1 | 116.8 (5) | C15—C16—F5 | 121.4 (7) |
| C5—C6—C1 | 122.9 (6) | C17—C16—F5 | 94.9 (6) |
| F1—C6—C1 | 120.1 (6) | C15—C16—H16A | 106.6 |
| O1—C7—N1 | 123.1 (5) | C17—C16—H16A | 106.6 |
| O1—C7—C5 | 125.0 (5) | F5—C16—H16A | 106.6 |
| N1—C7—C5 | 111.9 (5) | F6—C17—F8 | 115.2 (7) |
| O2—C8—N2 | 125.8 (5) | F6—C17—F7 | 95.9 (6) |
| O2—C8—N1 | 116.9 (4) | F8—C17—F7 | 134.6 (8) |
| N2—C8—N1 | 117.2 (5) | F6—C17—C16 | 105.8 (7) |
| N2—C9—C10 | 126.3 (5) | F8—C17—C16 | 95.3 (7) |
| N2—C9—C14 | 117.6 (5) | F7—C17—C16 | 107.7 (7) |
| C10—C9—C14 | 116.0 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2A···Cl2 | 0.86 | 2.43 | 2.892 (4) | 115 |
| N2—H2A···O1 | 0.86 | 1.98 | 2.664 (6) | 135 |
| N1—H1A···O2i | 0.86 | 1.98 | 2.814 (6) | 163 |
| C10—H10A···O2 | 0.93 | 2.28 | 2.851 (6) | 119 |
| Symmetry codes: (i) −x+1, −y+2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2A···Cl2 | 0.86 | 2.43 | 2.892 (4) | 115 |
| N2—H2A···O1 | 0.86 | 1.98 | 2.664 (6) | 135 |
| N1—H1A···O2i | 0.86 | 1.98 | 2.814 (6) | 163 |
| C10—H10A···O2 | 0.93 | 2.28 | 2.851 (6) | 119 |
| Symmetry codes: (i) −x+1, −y+2, −z+1. |
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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
Drabek, J. & Boeger, M. (1986). European Patent No. 179022.
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
The title compound is considered to belong to the fourth generation of insectides with properties such as high selectivity, low acute toxicity for mammals and high biological activity. It is generally recognized as a chitin-synthesis inhibitor that interrupts chitin-synthesis during the development and reproduction of the insectide. As part of our studies in this area, we report herein the crystal structure of the title compound.
In the molecule of the title compound, (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C9-C14) are, of course, planar, and the dihedral angle between them is A/B = 50.12 (3)°. The intramolecular N-H···O, C-H···O and N-H···Cl hydrogen bonds (Table 1) result in the formation of two six- and one five-membered non-planar rings: C (O1/N1/N2/C7/C8/H2A), D (O2/N2/C8-C10/H10A) and E (Cl2/N2/C9/C14/H2A). Rings C and D adopt twisted [φ = -169.19 (2)°, θ = 21.09 (3)° (for ring C) and φ = 178.48 (3)°, θ = 127.74 (3)° (for ring D)] conformations, having total puckering amplitudes, QT, of 0.113 (3) and 0.201 (3) Å, respectively (Cremer & Pople, 1975). Ring E adopts envelope conformation, with H2A atom displaced by 0.190 (3) Å from the plane of the other ring atoms.
In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.