PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1019.
Published online 2008 May 7. doi:  10.1107/S1600536808012634
PMCID: PMC2961588

trans-5-(4-Chloro­phen­yl)-N-cyclo­hexyl-4-methyl-2-oxo-1,3-thia­zolidine-3-carboxamide

Abstract

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.

Related literature

For the synthesis of the pesticide Hexythia­zox, see: Iwataki et al. (1981 [triangle]); Yamada et al. (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1019-scheme1.jpg

Experimental

Crystal data

  • C17H21ClN2O2S
  • M r = 352.88
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1019-efi1.jpg
  • a = 10.284 (4) Å
  • b = 11.799 (5) Å
  • c = 15.902 (5) Å
  • β = 111.830 (14)°
  • V = 1791.2 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 291 (2) K
  • 0.27 × 0.26 × 0.25 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.913, T max = 0.918
  • 17194 measured reflections
  • 4088 independent reflections
  • 3066 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.109
  • S = 1.06
  • 4088 reflections
  • 209 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012634/ng2450sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012634/ng2450Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Heilongjiang University for supporting this study.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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).

Figures

Fig. 1.
The molecular structure of (I), showing displacement ellipsoids at the 30% probability level for non-H atoms.
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.

Crystal data

C17H21ClN2O2SF000 = 744
Mr = 352.88Dx = 1.309 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12810 reflections
a = 10.284 (4) Åθ = 3.3–27.5º
b = 11.799 (5) ŵ = 0.34 mm1
c = 15.902 (5) ÅT = 291 (2) K
β = 111.830 (14)ºBlock, colorless
V = 1791.2 (12) Å30.27 × 0.26 × 0.25 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer4088 independent reflections
Radiation source: fine-focus sealed tube3066 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 291(2) Kθmax = 27.5º
ω scansθmin = 3.3º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)h = −13→11
Tmin = 0.913, Tmax = 0.918k = −15→15
17194 measured reflectionsl = −19→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-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 reflectionsΔρmax = 0.27 e Å3
209 parametersΔρmin = −0.27 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.5475 (2)1.00752 (16)0.78248 (11)0.0503 (4)
C20.5027 (2)1.07700 (16)0.83577 (12)0.0564 (5)
H10.55441.14050.86370.068*
C30.3794 (2)1.05051 (15)0.84691 (12)0.0540 (5)
H20.34801.09760.88230.065*
C40.30034 (18)0.95543 (13)0.80670 (10)0.0426 (4)
C50.3492 (2)0.88779 (15)0.75323 (11)0.0509 (4)
H30.29850.82390.72530.061*
C60.4717 (2)0.91368 (16)0.74085 (12)0.0547 (5)
H40.50270.86790.70450.066*
C70.17090 (18)0.93163 (14)0.82722 (12)0.0460 (4)
H50.12811.00460.83130.055*
C80.20030 (17)0.86779 (12)0.91720 (11)0.0392 (4)
H60.29820.88020.95670.047*
C90.1069 (2)0.90648 (17)0.96633 (16)0.0638 (5)
H70.01060.90160.92620.096*
H80.12890.98350.98590.096*
H90.12200.85881.01810.096*
C100.08671 (16)0.72176 (14)0.80822 (11)0.0418 (4)
C110.24351 (16)0.66650 (13)0.96508 (10)0.0382 (3)
C120.27713 (17)0.46582 (13)1.00756 (11)0.0426 (4)
H110.35000.49751.06150.051*
C130.34475 (19)0.37870 (16)0.96687 (12)0.0506 (4)
H120.42160.41340.95480.061*
H130.27670.35190.90980.061*
C140.3994 (2)0.27909 (16)1.03110 (15)0.0640 (6)
H140.43870.22271.00290.077*
H150.47340.30491.08610.077*
C150.2844 (3)0.22642 (17)1.05453 (16)0.0745 (7)
H160.32180.16371.09590.089*
H170.21270.19691.00000.089*
C160.2203 (2)0.3122 (2)1.09784 (15)0.0721 (6)
H180.29020.33711.15490.087*
H190.14410.27721.11050.087*
C170.1650 (2)0.41410 (18)1.03619 (13)0.0561 (5)
H200.08630.39080.98280.067*
H210.13180.47071.06770.067*
Cl10.70303 (6)1.03996 (6)0.76763 (4)0.07627 (19)
N10.18010 (13)0.74624 (10)0.89396 (8)0.0369 (3)
N20.21922 (17)0.55814 (12)0.94286 (10)0.0558 (4)
H100.16480.54220.88960.067*
O10.04055 (13)0.62916 (10)0.77874 (8)0.0545 (3)
O20.31689 (14)0.70170 (10)1.03933 (7)0.0520 (3)
S10.03912 (5)0.84657 (4)0.74263 (3)0.06226 (18)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0621 (11)0.0475 (10)0.0381 (8)−0.0070 (8)0.0149 (8)0.0067 (7)
C20.0721 (12)0.0442 (10)0.0500 (10)−0.0206 (9)0.0192 (9)−0.0081 (8)
C30.0723 (12)0.0393 (9)0.0511 (10)−0.0112 (8)0.0238 (9)−0.0112 (8)
C40.0533 (9)0.0299 (8)0.0347 (7)−0.0024 (7)0.0048 (7)0.0050 (6)
C50.0650 (11)0.0354 (9)0.0431 (9)−0.0083 (8)0.0092 (8)−0.0059 (7)
C60.0706 (12)0.0479 (11)0.0434 (9)−0.0012 (9)0.0187 (9)−0.0042 (8)
C70.0457 (9)0.0291 (8)0.0518 (9)0.0032 (7)0.0047 (7)0.0046 (7)
C80.0427 (8)0.0263 (7)0.0462 (8)−0.0002 (6)0.0137 (7)−0.0025 (6)
C90.0720 (13)0.0448 (11)0.0865 (15)0.0026 (9)0.0431 (12)−0.0134 (10)
C100.0359 (8)0.0384 (9)0.0428 (8)0.0002 (6)0.0049 (7)0.0003 (7)
C110.0430 (8)0.0312 (8)0.0389 (8)−0.0008 (6)0.0137 (7)−0.0006 (6)
C120.0500 (9)0.0285 (8)0.0398 (8)0.0008 (6)0.0058 (7)0.0011 (6)
C130.0475 (9)0.0485 (10)0.0537 (10)0.0018 (8)0.0164 (8)−0.0029 (8)
C140.0599 (12)0.0448 (11)0.0698 (12)0.0186 (9)0.0039 (10)−0.0057 (9)
C150.0853 (15)0.0351 (10)0.0751 (13)−0.0044 (10)−0.0026 (12)0.0133 (9)
C160.0732 (13)0.0748 (15)0.0641 (12)−0.0126 (12)0.0206 (11)0.0223 (11)
C170.0517 (10)0.0593 (12)0.0569 (10)0.0086 (9)0.0197 (9)0.0045 (9)
Cl10.0787 (4)0.0850 (4)0.0734 (3)−0.0163 (3)0.0380 (3)0.0019 (3)
N10.0414 (7)0.0269 (6)0.0374 (6)0.0017 (5)0.0087 (5)−0.0016 (5)
N20.0764 (10)0.0290 (7)0.0418 (7)−0.0011 (7)−0.0013 (7)0.0002 (6)
O10.0542 (7)0.0403 (7)0.0520 (7)−0.0077 (5)0.0001 (6)−0.0066 (5)
O20.0719 (8)0.0352 (6)0.0370 (6)−0.0045 (6)0.0066 (6)−0.0013 (5)
S10.0508 (3)0.0494 (3)0.0583 (3)−0.0045 (2)−0.0125 (2)0.0140 (2)

Geometric parameters (Å, °)

C1—C61.374 (3)C10—S11.7655 (18)
C1—C21.376 (3)C11—O21.2139 (19)
C1—Cl11.744 (2)C11—N21.325 (2)
C2—C31.380 (3)C11—N11.4286 (19)
C2—H10.9300C12—N21.464 (2)
C3—C41.393 (2)C12—C131.514 (2)
C3—H20.9300C12—C171.517 (3)
C4—C51.389 (3)C12—H110.9800
C4—C71.510 (3)C13—C141.521 (3)
C5—C61.379 (3)C13—H120.9700
C5—H30.9300C13—H130.9700
C6—H40.9300C14—C151.501 (3)
C7—C81.544 (2)C14—H140.9700
C7—S11.8159 (17)C14—H150.9700
C7—H50.9800C15—C161.507 (4)
C8—N11.4763 (19)C15—H160.9700
C8—C91.517 (3)C15—H170.9700
C8—H60.9800C16—C171.522 (3)
C9—H70.9600C16—H180.9700
C9—H80.9600C16—H190.9700
C9—H90.9600C17—H200.9700
C10—O11.214 (2)C17—H210.9700
C10—N11.375 (2)N2—H100.8445
C6—C1—C2121.10 (19)N2—C12—C17110.75 (15)
C6—C1—Cl1119.77 (16)C13—C12—C17112.11 (15)
C2—C1—Cl1119.14 (15)N2—C12—H11108.1
C1—C2—C3118.59 (17)C13—C12—H11108.1
C1—C2—H1120.7C17—C12—H11108.1
C3—C2—H1120.7C12—C13—C14110.57 (16)
C2—C3—C4122.04 (18)C12—C13—H12109.5
C2—C3—H2119.0C14—C13—H12109.5
C4—C3—H2119.0C12—C13—H13109.5
C5—C4—C3117.47 (18)C14—C13—H13109.5
C5—C4—C7125.03 (15)H12—C13—H13108.1
C3—C4—C7117.46 (16)C15—C14—C13110.99 (16)
C6—C5—C4121.16 (16)C15—C14—H14109.4
C6—C5—H3119.4C13—C14—H14109.4
C4—C5—H3119.4C15—C14—H15109.4
C1—C6—C5119.64 (18)C13—C14—H15109.4
C1—C6—H4120.2H14—C14—H15108.0
C5—C6—H4120.2C14—C15—C16110.77 (17)
C4—C7—C8113.97 (13)C14—C15—H16109.5
C4—C7—S1114.69 (13)C16—C15—H16109.5
C8—C7—S1104.59 (11)C14—C15—H17109.5
C4—C7—H5107.8C16—C15—H17109.5
C8—C7—H5107.8H16—C15—H17108.1
S1—C7—H5107.8C15—C16—C17111.00 (18)
N1—C8—C9111.37 (14)C15—C16—H18109.4
N1—C8—C7106.33 (13)C17—C16—H18109.4
C9—C8—C7112.78 (15)C15—C16—H19109.4
N1—C8—H6108.8C17—C16—H19109.4
C9—C8—H6108.8H18—C16—H19108.0
C7—C8—H6108.8C12—C17—C16111.58 (16)
C8—C9—H7109.5C12—C17—H20109.3
C8—C9—H8109.5C16—C17—H20109.3
H7—C9—H8109.5C12—C17—H21109.3
C8—C9—H9109.5C16—C17—H21109.3
H7—C9—H9109.5H20—C17—H21108.0
H8—C9—H9109.5C10—N1—C11126.26 (13)
O1—C10—N1126.92 (15)C10—N1—C8115.70 (12)
O1—C10—S1122.68 (12)C11—N1—C8117.47 (12)
N1—C10—S1110.40 (11)C11—N2—C12122.90 (14)
O2—C11—N2125.23 (15)C11—N2—H10118.1
O2—C11—N1118.71 (14)C12—N2—H10118.9
N2—C11—N1116.04 (13)C10—S1—C793.26 (8)
N2—C12—C13109.64 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H10···O10.842.032.706 (2)137
C2—H1···O2i0.932.473.386 (2)170
C5—H3···S10.932.793.168 (2)105
C12—H11···O20.982.442.831 (2)103

Symmetry codes: (i) −x+1, −y+2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2450).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Iwataki, I., Kaeriyama, M., Matsui, N. & Yamada, T. (1981). German Patent 3 037 105.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yamada, T., Kaeriyama, M., Matsui, N. & Yoneda, H. (1983). Japan Patent 58 110 577.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography