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

Yu, Y.-H.; Liu, J.-L.; Niu, L.-Z.; Hou, G.-F.; Gao, J.-S.

doi:10.1107/S1600536808012634

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1019

doi:10.1107/S1600536808012634

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

Ying-Hui Yu,^a Ji-Long Liu,^a Li-Zhong Niu,^a Guang-Feng Hou ^a and Jin-Sheng Gao ^a ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 24 April 2008; accepted 30 April 2008; online 7 May 2008)

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 ); Yamada et al. (1983 ).

Experimental

Crystal data

C₁₇H₂₁ClN₂O₂S
M_r = 352.88
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.109
S = 1.06
4088 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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 code: (i) -x+1, -y+2, -z+2.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; 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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

For the synthesis of the pesticide Hexythiazox, see: Iwataki et al. (1981); Yamada et al. (1983). For related literature, see: Oxazolidone (1981); Soda (1983).

Experimental top

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.

Computing details top

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).

Figures top

	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.

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

Crystal data top

C₁₇H₂₁ClN₂O₂S	F(000) = 744
M_r = 352.88	D_x = 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 = 3.3–27.5°
b = 11.799 (5) Å	µ = 0.34 mm⁻¹
c = 15.902 (5) Å	T = 291 K
β = 111.830 (14)°	Block, colorless
V = 1791.2 (12) Å³	0.27 × 0.26 × 0.25 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4088 independent reflections
Radiation source: fine-focus sealed tube	3066 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→11
T_min = 0.913, T_max = 0.918	k = −15→15
17194 measured reflections	l = −19→20

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0513P)² + 0.331P] where P = (F_o² + 2F_c²)/3
4088 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₂₁ClN₂O₂S	V = 1791.2 (12) Å³
M_r = 352.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.284 (4) Å	µ = 0.34 mm⁻¹
b = 11.799 (5) Å	T = 291 K
c = 15.902 (5) Å	0.27 × 0.26 × 0.25 mm
β = 111.830 (14)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4088 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3066 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.918	R_int = 0.033
17194 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.06	Δρ_max = 0.27 e Å⁻³
4088 reflections	Δρ_min = −0.27 e Å⁻³
209 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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 code: (i) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁ClN₂O₂S
M_r	352.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	10.284 (4), 11.799 (5), 15.902 (5)
β (°)	111.830 (14)
V (Å³)	1791.2 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.27 × 0.26 × 0.25

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.913, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	17194, 4088, 3066
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.06
No. of reflections	4088
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H10···O1	0.84	2.03	2.706 (2)	136.6
C2—H1···O2ⁱ	0.93	2.47	3.386 (2)	170.2
C5—H3···S1	0.93	2.79	3.168 (2)	105.2
C12—H11···O2	0.98	2.44	2.831 (2)	103.3

Symmetry code: (i) −x+1, −y+2, −z+2.

Acknowledgements

The authors thank Heilongjiang University for supporting this study.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1019

doi:10.1107/S1600536808012634

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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