Acta Cryst. (2008). E64, o1019 [ doi:10.1107/S1600536808012634 ]
The title pesticide, C17H21ClN2O2S, has a trans arrangement of the 4-chlorophenyl and 4-methyl substituents of the thiazolidine ring; the structure features an intramolecular amide-ring carbonyl N-H
O hydrogen bond. The thiazolidine ring is almost planar, the largest deviation being 0.199 (1) Å for the methyl-substitued C atom, and the cyclohexane ring has a chair conformation.
Hexythiazox was synthesized by the reaction of 5-(4-chlorophenyl)-4-methylthiazolidin-2-one and isocyanatocyclohexane in toluene solution in the patent litearture. Crystals suitable for X-ray experiments were obtained by slow evaporation of an ethanol solution.
H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), C—H = 0.98 Å (methine), C—H = 0.97 Å (methylene), C—H = 0.96 Å (methyl) and with Uiso(H) = 1.2Ueq(C). N-H atoms were initially located in a difference Fourier map but they were treated as riding on their parent atoms with N—H = 0.85 Å, and with Uiso(H) = 1.2Ueq(O).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./ng2450fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level for non-H atoms. |
![[Figure 2]](./ng2450fig2thm.gif)
| Fig. 2. A partial packing view, showing the three-dimensional hydrogen-bonding network. Dashed lines indicate the hydrogen-bonding interactions. H atoms not involved in hydrogen bonds have been omitted for clarity. |
| C17H21ClN2O2S | F000 = 744 |
| Mr = 352.88 | Dx = 1.309 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 12810 reflections |
| a = 10.284 (4) Å | θ = 3.3–27.5º |
| b = 11.799 (5) Å | µ = 0.34 mm−1 |
| c = 15.902 (5) Å | T = 291 (2) K |
| β = 111.830 (14)º | Block, colorless |
| V = 1791.2 (12) Å3 | 0.27 × 0.26 × 0.25 mm |
| Z = 4 |
| Rigaku R-AXIS RAPID diffractometer | 4088 independent reflections |
| Radiation source: fine-focus sealed tube | 3066 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.033 |
| T = 291(2) K | θmax = 27.5º |
| ω scans | θmin = 3.3º |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→11 |
| Tmin = 0.913, Tmax = 0.918 | k = −15→15 |
| 17194 measured reflections | l = −19→20 |
| 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)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0513P)2 + 0.331P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max = 0.001 |
| 4088 reflections | Δρmax = 0.27 e Å−3 |
| 209 parameters | Δρmin = −0.27 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C17H21ClN2O2S | V = 1791.2 (12) Å3 |
| Mr = 352.88 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 10.284 (4) Å | µ = 0.34 mm−1 |
| b = 11.799 (5) Å | T = 291 (2) K |
| c = 15.902 (5) Å | 0.27 × 0.26 × 0.25 mm |
| β = 111.830 (14)º |
| Rigaku R-AXIS RAPID diffractometer | 4088 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3066 reflections with I > 2σ(I) |
| Tmin = 0.913, Tmax = 0.918 | Rint = 0.033 |
| 17194 measured reflections |
| R[F2 > 2σ(F2)] = 0.041 | 209 parameters |
| wR(F2) = 0.109 | H-atom parameters constrained |
| S = 1.06 | Δρmax = 0.27 e Å−3 |
| 4088 reflections | Δρmin = −0.27 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
| C1 | 0.5475 (2) | 1.00752 (16) | 0.78248 (11) | 0.0503 (4) | |
| C2 | 0.5027 (2) | 1.07700 (16) | 0.83577 (12) | 0.0564 (5) | |
| H1 | 0.5544 | 1.1405 | 0.8637 | 0.068* | |
| C3 | 0.3794 (2) | 1.05051 (15) | 0.84691 (12) | 0.0540 (5) | |
| H2 | 0.3480 | 1.0976 | 0.8823 | 0.065* | |
| C4 | 0.30034 (18) | 0.95543 (13) | 0.80670 (10) | 0.0426 (4) | |
| C5 | 0.3492 (2) | 0.88779 (15) | 0.75323 (11) | 0.0509 (4) | |
| H3 | 0.2985 | 0.8239 | 0.7253 | 0.061* | |
| C6 | 0.4717 (2) | 0.91368 (16) | 0.74085 (12) | 0.0547 (5) | |
| H4 | 0.5027 | 0.8679 | 0.7045 | 0.066* | |
| C7 | 0.17090 (18) | 0.93163 (14) | 0.82722 (12) | 0.0460 (4) | |
| H5 | 0.1281 | 1.0046 | 0.8313 | 0.055* | |
| C8 | 0.20030 (17) | 0.86779 (12) | 0.91720 (11) | 0.0392 (4) | |
| H6 | 0.2982 | 0.8802 | 0.9567 | 0.047* | |
| C9 | 0.1069 (2) | 0.90648 (17) | 0.96633 (16) | 0.0638 (5) | |
| H7 | 0.0106 | 0.9016 | 0.9262 | 0.096* | |
| H8 | 0.1289 | 0.9835 | 0.9859 | 0.096* | |
| H9 | 0.1220 | 0.8588 | 1.0181 | 0.096* | |
| C10 | 0.08671 (16) | 0.72176 (14) | 0.80822 (11) | 0.0418 (4) | |
| C11 | 0.24351 (16) | 0.66650 (13) | 0.96508 (10) | 0.0382 (3) | |
| C12 | 0.27713 (17) | 0.46582 (13) | 1.00756 (11) | 0.0426 (4) | |
| H11 | 0.3500 | 0.4975 | 1.0615 | 0.051* | |
| C13 | 0.34475 (19) | 0.37870 (16) | 0.96687 (12) | 0.0506 (4) | |
| H12 | 0.4216 | 0.4134 | 0.9548 | 0.061* | |
| H13 | 0.2767 | 0.3519 | 0.9098 | 0.061* | |
| C14 | 0.3994 (2) | 0.27909 (16) | 1.03110 (15) | 0.0640 (6) | |
| H14 | 0.4387 | 0.2227 | 1.0029 | 0.077* | |
| H15 | 0.4734 | 0.3049 | 1.0861 | 0.077* | |
| C15 | 0.2844 (3) | 0.22642 (17) | 1.05453 (16) | 0.0745 (7) | |
| H16 | 0.3218 | 0.1637 | 1.0959 | 0.089* | |
| H17 | 0.2127 | 0.1969 | 1.0000 | 0.089* | |
| C16 | 0.2203 (2) | 0.3122 (2) | 1.09784 (15) | 0.0721 (6) | |
| H18 | 0.2902 | 0.3371 | 1.1549 | 0.087* | |
| H19 | 0.1441 | 0.2772 | 1.1105 | 0.087* | |
| C17 | 0.1650 (2) | 0.41410 (18) | 1.03619 (13) | 0.0561 (5) | |
| H20 | 0.0863 | 0.3908 | 0.9828 | 0.067* | |
| H21 | 0.1318 | 0.4707 | 1.0677 | 0.067* | |
| Cl1 | 0.70303 (6) | 1.03996 (6) | 0.76763 (4) | 0.07627 (19) | |
| N1 | 0.18010 (13) | 0.74624 (10) | 0.89396 (8) | 0.0369 (3) | |
| N2 | 0.21922 (17) | 0.55814 (12) | 0.94286 (10) | 0.0558 (4) | |
| H10 | 0.1648 | 0.5422 | 0.8896 | 0.067* | |
| O1 | 0.04055 (13) | 0.62916 (10) | 0.77874 (8) | 0.0545 (3) | |
| O2 | 0.31689 (14) | 0.70170 (10) | 1.03933 (7) | 0.0520 (3) | |
| S1 | 0.03912 (5) | 0.84657 (4) | 0.74263 (3) | 0.06226 (18) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0621 (11) | 0.0475 (10) | 0.0381 (8) | −0.0070 (8) | 0.0149 (8) | 0.0067 (7) |
| C2 | 0.0721 (12) | 0.0442 (10) | 0.0500 (10) | −0.0206 (9) | 0.0192 (9) | −0.0081 (8) |
| C3 | 0.0723 (12) | 0.0393 (9) | 0.0511 (10) | −0.0112 (8) | 0.0238 (9) | −0.0112 (8) |
| C4 | 0.0533 (9) | 0.0299 (8) | 0.0347 (7) | −0.0024 (7) | 0.0048 (7) | 0.0050 (6) |
| C5 | 0.0650 (11) | 0.0354 (9) | 0.0431 (9) | −0.0083 (8) | 0.0092 (8) | −0.0059 (7) |
| C6 | 0.0706 (12) | 0.0479 (11) | 0.0434 (9) | −0.0012 (9) | 0.0187 (9) | −0.0042 (8) |
| C7 | 0.0457 (9) | 0.0291 (8) | 0.0518 (9) | 0.0032 (7) | 0.0047 (7) | 0.0046 (7) |
| C8 | 0.0427 (8) | 0.0263 (7) | 0.0462 (8) | −0.0002 (6) | 0.0137 (7) | −0.0025 (6) |
| C9 | 0.0720 (13) | 0.0448 (11) | 0.0865 (15) | 0.0026 (9) | 0.0431 (12) | −0.0134 (10) |
| C10 | 0.0359 (8) | 0.0384 (9) | 0.0428 (8) | 0.0002 (6) | 0.0049 (7) | 0.0003 (7) |
| C11 | 0.0430 (8) | 0.0312 (8) | 0.0389 (8) | −0.0008 (6) | 0.0137 (7) | −0.0006 (6) |
| C12 | 0.0500 (9) | 0.0285 (8) | 0.0398 (8) | 0.0008 (6) | 0.0058 (7) | 0.0011 (6) |
| C13 | 0.0475 (9) | 0.0485 (10) | 0.0537 (10) | 0.0018 (8) | 0.0164 (8) | −0.0029 (8) |
| C14 | 0.0599 (12) | 0.0448 (11) | 0.0698 (12) | 0.0186 (9) | 0.0039 (10) | −0.0057 (9) |
| C15 | 0.0853 (15) | 0.0351 (10) | 0.0751 (13) | −0.0044 (10) | −0.0026 (12) | 0.0133 (9) |
| C16 | 0.0732 (13) | 0.0748 (15) | 0.0641 (12) | −0.0126 (12) | 0.0206 (11) | 0.0223 (11) |
| C17 | 0.0517 (10) | 0.0593 (12) | 0.0569 (10) | 0.0086 (9) | 0.0197 (9) | 0.0045 (9) |
| Cl1 | 0.0787 (4) | 0.0850 (4) | 0.0734 (3) | −0.0163 (3) | 0.0380 (3) | 0.0019 (3) |
| N1 | 0.0414 (7) | 0.0269 (6) | 0.0374 (6) | 0.0017 (5) | 0.0087 (5) | −0.0016 (5) |
| N2 | 0.0764 (10) | 0.0290 (7) | 0.0418 (7) | −0.0011 (7) | −0.0013 (7) | 0.0002 (6) |
| O1 | 0.0542 (7) | 0.0403 (7) | 0.0520 (7) | −0.0077 (5) | 0.0001 (6) | −0.0066 (5) |
| O2 | 0.0719 (8) | 0.0352 (6) | 0.0370 (6) | −0.0045 (6) | 0.0066 (6) | −0.0013 (5) |
| S1 | 0.0508 (3) | 0.0494 (3) | 0.0583 (3) | −0.0045 (2) | −0.0125 (2) | 0.0140 (2) |
| C1—C6 | 1.374 (3) | C10—S1 | 1.7655 (18) |
| C1—C2 | 1.376 (3) | C11—O2 | 1.2139 (19) |
| C1—Cl1 | 1.744 (2) | C11—N2 | 1.325 (2) |
| C2—C3 | 1.380 (3) | C11—N1 | 1.4286 (19) |
| C2—H1 | 0.9300 | C12—N2 | 1.464 (2) |
| C3—C4 | 1.393 (2) | C12—C13 | 1.514 (2) |
| C3—H2 | 0.9300 | C12—C17 | 1.517 (3) |
| C4—C5 | 1.389 (3) | C12—H11 | 0.9800 |
| C4—C7 | 1.510 (3) | C13—C14 | 1.521 (3) |
| C5—C6 | 1.379 (3) | C13—H12 | 0.9700 |
| C5—H3 | 0.9300 | C13—H13 | 0.9700 |
| C6—H4 | 0.9300 | C14—C15 | 1.501 (3) |
| C7—C8 | 1.544 (2) | C14—H14 | 0.9700 |
| C7—S1 | 1.8159 (17) | C14—H15 | 0.9700 |
| C7—H5 | 0.9800 | C15—C16 | 1.507 (4) |
| C8—N1 | 1.4763 (19) | C15—H16 | 0.9700 |
| C8—C9 | 1.517 (3) | C15—H17 | 0.9700 |
| C8—H6 | 0.9800 | C16—C17 | 1.522 (3) |
| C9—H7 | 0.9600 | C16—H18 | 0.9700 |
| C9—H8 | 0.9600 | C16—H19 | 0.9700 |
| C9—H9 | 0.9600 | C17—H20 | 0.9700 |
| C10—O1 | 1.214 (2) | C17—H21 | 0.9700 |
| C10—N1 | 1.375 (2) | N2—H10 | 0.8445 |
| C6—C1—C2 | 121.10 (19) | N2—C12—C17 | 110.75 (15) |
| C6—C1—Cl1 | 119.77 (16) | C13—C12—C17 | 112.11 (15) |
| C2—C1—Cl1 | 119.14 (15) | N2—C12—H11 | 108.1 |
| C1—C2—C3 | 118.59 (17) | C13—C12—H11 | 108.1 |
| C1—C2—H1 | 120.7 | C17—C12—H11 | 108.1 |
| C3—C2—H1 | 120.7 | C12—C13—C14 | 110.57 (16) |
| C2—C3—C4 | 122.04 (18) | C12—C13—H12 | 109.5 |
| C2—C3—H2 | 119.0 | C14—C13—H12 | 109.5 |
| C4—C3—H2 | 119.0 | C12—C13—H13 | 109.5 |
| C5—C4—C3 | 117.47 (18) | C14—C13—H13 | 109.5 |
| C5—C4—C7 | 125.03 (15) | H12—C13—H13 | 108.1 |
| C3—C4—C7 | 117.46 (16) | C15—C14—C13 | 110.99 (16) |
| C6—C5—C4 | 121.16 (16) | C15—C14—H14 | 109.4 |
| C6—C5—H3 | 119.4 | C13—C14—H14 | 109.4 |
| C4—C5—H3 | 119.4 | C15—C14—H15 | 109.4 |
| C1—C6—C5 | 119.64 (18) | C13—C14—H15 | 109.4 |
| C1—C6—H4 | 120.2 | H14—C14—H15 | 108.0 |
| C5—C6—H4 | 120.2 | C14—C15—C16 | 110.77 (17) |
| C4—C7—C8 | 113.97 (13) | C14—C15—H16 | 109.5 |
| C4—C7—S1 | 114.69 (13) | C16—C15—H16 | 109.5 |
| C8—C7—S1 | 104.59 (11) | C14—C15—H17 | 109.5 |
| C4—C7—H5 | 107.8 | C16—C15—H17 | 109.5 |
| C8—C7—H5 | 107.8 | H16—C15—H17 | 108.1 |
| S1—C7—H5 | 107.8 | C15—C16—C17 | 111.00 (18) |
| N1—C8—C9 | 111.37 (14) | C15—C16—H18 | 109.4 |
| N1—C8—C7 | 106.33 (13) | C17—C16—H18 | 109.4 |
| C9—C8—C7 | 112.78 (15) | C15—C16—H19 | 109.4 |
| N1—C8—H6 | 108.8 | C17—C16—H19 | 109.4 |
| C9—C8—H6 | 108.8 | H18—C16—H19 | 108.0 |
| C7—C8—H6 | 108.8 | C12—C17—C16 | 111.58 (16) |
| C8—C9—H7 | 109.5 | C12—C17—H20 | 109.3 |
| C8—C9—H8 | 109.5 | C16—C17—H20 | 109.3 |
| H7—C9—H8 | 109.5 | C12—C17—H21 | 109.3 |
| C8—C9—H9 | 109.5 | C16—C17—H21 | 109.3 |
| H7—C9—H9 | 109.5 | H20—C17—H21 | 108.0 |
| H8—C9—H9 | 109.5 | C10—N1—C11 | 126.26 (13) |
| O1—C10—N1 | 126.92 (15) | C10—N1—C8 | 115.70 (12) |
| O1—C10—S1 | 122.68 (12) | C11—N1—C8 | 117.47 (12) |
| N1—C10—S1 | 110.40 (11) | C11—N2—C12 | 122.90 (14) |
| O2—C11—N2 | 125.23 (15) | C11—N2—H10 | 118.1 |
| O2—C11—N1 | 118.71 (14) | C12—N2—H10 | 118.9 |
| N2—C11—N1 | 116.04 (13) | C10—S1—C7 | 93.26 (8) |
| N2—C12—C13 | 109.64 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H10···O1 | 0.84 | 2.03 | 2.706 (2) | 137 |
| C2—H1···O2i | 0.93 | 2.47 | 3.386 (2) | 170 |
| C5—H3···S1 | 0.93 | 2.79 | 3.168 (2) | 105 |
| C12—H11···O2 | 0.98 | 2.44 | 2.831 (2) | 103 |
| Symmetry codes: (i) −x+1, −y+2, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H10···O1 | 0.84 | 2.03 | 2.706 (2) | 137 |
| C2—H1···O2i | 0.93 | 2.47 | 3.386 (2) | 170 |
| C5—H3···S1 | 0.93 | 2.79 | 3.168 (2) | 105 |
| C12—H11···O2 | 0.98 | 2.44 | 2.831 (2) | 103 |
| Symmetry codes: (i) −x+1, −y+2, −z+2. |
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Hexythiazox, chemically named trans-5-(4-chlorophenyl)- N-cyclohexyl-4-methyl-2-oxo-3-thiazolidinecarboxamide, is known as a high efficiency of pesticide. In this paper, we first report the crystal structure of hexythiazox (I).
The title compound (I), consists of a planar phenyl ring (A), a S-contained five-numbers ring (B) and a cyclohexane ring (C). The S-contained five-numbers ring is alomst coplanar, with the largest deviation being 0.199 (1) Å for atom C8, and the cyclohexane ring is chair forms. The three rings make the following dihedral angles: A/B 82.20 (0.06)°, A/C 54.22 (0.07)° and B/C 81.70 (0.06)°.
In the crystal structure, an extensive network of intramolecular N—H···O and intermolecular C—H···O hydrogen bonds stabilizes the packing (Table 1; Fig. 2).