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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3285.
Published online 2010 November 24. doi:  10.1107/S1600536810047884
PMCID: PMC3011722

N-(3-Octyl-4-oxo-1,3-thia­zolidin-2-yl­idene)benzamide

Abstract

In the title compound, C18H24N2O2S, the thia­zolidinone ring is almost coplanar [maximum atomic deviation = 0.017 (3) Å], and is coplanar with the phenyl ring [dihedral angle = 0.62 (13)°]. The octyl group displays an extended conformation. In the crystal, weak inter­molecular C—H(...)O hydrogen bonds link the mol­ecules into supra­molecular chains along [210].

Related literature

For pharmaceutical applications of thia­zolidinones, see: Dwivedi et al. (1972 [triangle]); Chandrakant et al. (2004 [triangle]). For the synthesis, see: Peng et al. (2004 [triangle]).

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Object name is e-66-o3285-scheme1.jpg

Experimental

Crystal data

  • C18H24N2O2S
  • M r = 332.45
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3285-efi1.jpg
  • a = 5.3342 (3) Å
  • b = 8.6196 (5) Å
  • c = 20.0775 (12) Å
  • α = 97.008 (5)°
  • β = 92.870 (4)°
  • γ = 99.477 (4)°
  • V = 901.41 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 293 K
  • 0.26 × 0.18 × 0.16 mm

Data collection

  • Oxford Diffraction Nova A diffractometer
  • 8685 measured reflections
  • 3205 independent reflections
  • 2371 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.145
  • S = 1.03
  • 3205 reflections
  • 208 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047884/xu5080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047884/xu5080Isup2.hkl

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

Acknowledgments

The authors thank the Natural Science Foundation of Zhejiang Province, China, for financial support (grant No. Y4080234).

supplementary crystallographic information

Comment

Thiazolidinones have broad applications as anticonvulsant (Dwivedi et al., 1972) and anti-microbial drugs (Chandrakant et al., 2004). We report here the structure of a new thiazolidinone derivative, I, Fig. 2.

The thiazolidinyl ring and phenyl ring are almost co-planar with the dihedral angle of 0.67 (0.18)°. In the crystal structure, weak intermolecular C—H···O hydrogen bonds, Table 1, link the molecules to form one-dimensional supra-molecular chains, Fig. 1.

Experimental

The title compound was prepared followed to the procedure reported by Peng et al. (2004). NH4SCN (0.152 g, 2 mmol) and [bmim][PF4] (2 ml) was mixed in a 50 ml flask equipped with a dropping funnel and then was cooled in an ice-water bath. Next benzoyl chloride(0.284 g, 2 mmol) was added drop by drop and stirred for a further 20 min (disappearance of the raw material was monitored by TLC). n-Octylamine (2 mmol) was then added to the same reaction vessel at room temperature and the mixture was stirred for 20 min more. N-benzoyl-N'-octylthiourea was formed. After that, ethyl chloroacetate (2.4 mmol) and anhydrous sodium acetate (0.196 g, 2.4 mmol) was added to the flask, and the mixture was heated at 80°C for 2 h. The salts were firstly leached with water (10 ml×2), and the crude product was collected by filtration. Recrystallization from ethanol gave pure product as a yellow crystalline solid.

Refinement

H atoms were placed in calculated positions with C—H = 0.93-0.97 Å and refined in riding mode with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Figures

Fig. 1.
The molecular structure of the title compound with 40% probability displacement ellipsoids.
Fig. 2.
Crystal packing for I viewed down the a axis.

Crystal data

C18H24N2O2SZ = 2
Mr = 332.45F(000) = 356
Triclinic, P1Dx = 1.225 Mg m3
Hall symbol: -p 1Mo Kα radiation, λ = 0.71073 Å
a = 5.3342 (3) ÅCell parameters from 2856 reflections
b = 8.6196 (5) Åθ = 4.5–67.0°
c = 20.0775 (12) ŵ = 0.19 mm1
α = 97.008 (5)°T = 293 K
β = 92.870 (4)°Prism, yellow
γ = 99.477 (4)°0.26 × 0.18 × 0.16 mm
V = 901.41 (9) Å3

Data collection

Oxford Diffraction Nova A diffractometer2371 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
graphiteθmax = 25.1°, θmin = 2.1°
ω scansh = −6→5
8685 measured reflectionsk = −9→10
3205 independent reflectionsl = −23→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0633P)2 + 0.4272P] where P = (Fo2 + 2Fc2)/3
3205 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.17 e Å3

Special details

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.

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

xyzUiso*/Ueq
N20.2339 (4)0.3596 (2)0.30556 (10)0.0496 (5)
N1−0.1304 (4)0.2176 (2)0.34097 (10)0.0492 (5)
C90.4393 (5)0.4805 (3)0.32305 (14)0.0533 (6)
C80.0680 (5)0.3283 (3)0.35492 (12)0.0464 (6)
C100.4427 (5)0.5499 (3)0.39502 (14)0.0585 (7)
H10A0.44220.66300.39820.070*
H10B0.59520.53370.41970.070*
O1−0.2580 (4)0.2654 (2)0.44909 (9)0.0680 (6)
O20.5957 (4)0.5200 (2)0.28388 (11)0.0733 (6)
S10.16338 (13)0.45285 (8)0.42998 (3)0.0534 (2)
C7−0.2882 (5)0.1901 (3)0.39283 (13)0.0508 (6)
C1−0.5089 (5)0.0581 (3)0.37455 (13)0.0495 (6)
C110.1963 (5)0.2715 (3)0.23775 (13)0.0569 (7)
H11A0.11250.16380.24020.068*
H11B0.36130.26630.22020.068*
C2−0.5494 (5)−0.0279 (3)0.31152 (14)0.0598 (7)
H2−0.4341−0.00640.27920.072*
C6−0.6820 (5)0.0229 (3)0.42264 (15)0.0606 (7)
H6−0.65550.07950.46560.073*
C5−0.8909 (6)−0.0944 (4)0.40707 (18)0.0712 (8)
H5−1.0049−0.11720.43950.085*
C4−0.9324 (6)−0.1783 (4)0.34373 (19)0.0735 (9)
H4−1.0759−0.25650.33310.088*
C13−0.0006 (7)0.2535 (5)0.12043 (15)0.0816 (10)
H13A0.16340.25760.10130.098*
H13B−0.06580.14320.12410.098*
C120.0397 (6)0.3448 (4)0.18997 (14)0.0730 (9)
H12A0.12410.45230.18720.088*
H12B−0.12490.35080.20770.088*
C3−0.7605 (6)−0.1462 (4)0.29574 (17)0.0721 (9)
H3−0.7867−0.20410.25300.086*
C15−0.2276 (8)0.2222 (6)0.00389 (18)0.1053 (13)
H15A−0.28380.11090.00760.126*
H15B−0.06790.2307−0.01760.126*
C14−0.1781 (8)0.3108 (5)0.07302 (17)0.0976 (12)
H14A−0.34010.30900.09300.117*
H14B−0.11060.42070.06910.117*
C17−0.4809 (10)0.1911 (7)−0.1089 (2)0.1358 (19)
H17A−0.53180.0792−0.10550.163*
H17B−0.32620.2022−0.13260.163*
C16−0.4209 (9)0.2749 (6)−0.04136 (19)0.1114 (14)
H16A−0.57840.2690−0.01890.134*
H16B−0.36210.3859−0.04520.134*
C18−0.6818 (9)0.2415 (7)−0.1504 (2)0.1289 (18)
H18A−0.70810.1765−0.19330.193*
H18B−0.63040.3505−0.15670.193*
H18C−0.83750.2302−0.12800.193*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N20.0480 (11)0.0528 (12)0.0450 (11)0.0005 (10)0.0052 (9)0.0055 (9)
N10.0485 (11)0.0499 (12)0.0463 (12)0.0009 (10)0.0016 (9)0.0058 (9)
C90.0484 (14)0.0498 (15)0.0606 (16)0.0042 (12)0.0051 (12)0.0080 (12)
C80.0474 (13)0.0485 (14)0.0435 (13)0.0085 (11)0.0025 (10)0.0074 (11)
C100.0509 (15)0.0552 (16)0.0643 (17)−0.0023 (12)−0.0024 (13)0.0066 (13)
O10.0687 (12)0.0731 (13)0.0520 (11)−0.0099 (10)0.0110 (9)−0.0052 (10)
O20.0613 (12)0.0734 (14)0.0804 (14)−0.0074 (10)0.0208 (11)0.0104 (11)
S10.0525 (4)0.0583 (4)0.0445 (4)0.0010 (3)0.0008 (3)−0.0002 (3)
C70.0477 (14)0.0528 (15)0.0519 (15)0.0065 (12)0.0025 (11)0.0100 (12)
C10.0447 (13)0.0500 (14)0.0537 (15)0.0063 (11)0.0025 (11)0.0099 (12)
C110.0572 (15)0.0606 (16)0.0497 (15)0.0037 (13)0.0105 (12)0.0012 (13)
C20.0558 (16)0.0597 (17)0.0600 (17)−0.0015 (13)0.0014 (13)0.0091 (14)
C60.0517 (15)0.0645 (18)0.0671 (18)0.0083 (13)0.0082 (13)0.0153 (14)
C50.0541 (17)0.073 (2)0.089 (2)0.0048 (15)0.0147 (16)0.0263 (18)
C40.0518 (16)0.0626 (19)0.102 (3)−0.0080 (14)−0.0050 (17)0.0241 (18)
C130.088 (2)0.097 (3)0.0558 (18)0.011 (2)0.0007 (16)0.0037 (17)
C120.077 (2)0.086 (2)0.0543 (17)0.0132 (17)0.0032 (15)0.0036 (16)
C30.0703 (19)0.0631 (19)0.073 (2)−0.0051 (15)−0.0111 (16)0.0013 (15)
C150.116 (3)0.130 (4)0.063 (2)0.014 (3)−0.010 (2)0.004 (2)
C140.105 (3)0.122 (3)0.063 (2)0.018 (2)−0.0113 (19)0.009 (2)
C170.153 (4)0.185 (5)0.068 (3)0.049 (4)−0.022 (3)−0.004 (3)
C160.120 (3)0.137 (4)0.073 (2)0.021 (3)−0.012 (2)0.006 (2)
C180.129 (4)0.182 (5)0.076 (3)0.042 (4)−0.017 (3)0.003 (3)

Geometric parameters (Å, °)

N2—C91.380 (3)C4—C31.384 (5)
N2—C81.383 (3)C4—H40.9300
N2—C111.463 (3)C13—C141.492 (5)
N1—C81.297 (3)C13—C121.504 (4)
N1—C71.390 (3)C13—H13A0.9700
C9—O21.212 (3)C13—H13B0.9700
C9—C101.493 (4)C12—H12A0.9700
C8—S11.741 (2)C12—H12B0.9700
C10—S11.802 (3)C3—H30.9300
C10—H10A0.9700C15—C141.489 (5)
C10—H10B0.9700C15—C161.502 (5)
O1—C71.221 (3)C15—H15A0.9700
C7—C11.493 (4)C15—H15B0.9700
C1—C21.374 (4)C14—H14A0.9700
C1—C61.395 (4)C14—H14B0.9700
C11—C121.503 (4)C17—C161.451 (5)
C11—H11A0.9700C17—C181.477 (6)
C11—H11B0.9700C17—H17A0.9700
C2—C31.384 (4)C17—H17B0.9700
C2—H20.9300C16—H16A0.9700
C6—C51.371 (4)C16—H16B0.9700
C6—H60.9300C18—H18A0.9600
C5—C41.373 (5)C18—H18B0.9600
C5—H50.9300C18—H18C0.9600
C9—N2—C8116.6 (2)C12—C13—H13A108.5
C9—N2—C11120.8 (2)C14—C13—H13B108.5
C8—N2—C11122.6 (2)C12—C13—H13B108.5
C8—N1—C7116.6 (2)H13A—C13—H13B107.5
O2—C9—N2122.6 (3)C11—C12—C13113.0 (3)
O2—C9—C10126.0 (2)C11—C12—H12A109.0
N2—C9—C10111.4 (2)C13—C12—H12A109.0
N1—C8—N2119.3 (2)C11—C12—H12B109.0
N1—C8—S1128.94 (19)C13—C12—H12B109.0
N2—C8—S1111.79 (18)H12A—C12—H12B107.8
C9—C10—S1108.19 (18)C2—C3—C4119.8 (3)
C9—C10—H10A110.1C2—C3—H3120.1
S1—C10—H10A110.1C4—C3—H3120.1
C9—C10—H10B110.1C14—C15—C16116.1 (4)
S1—C10—H10B110.1C14—C15—H15A108.3
H10A—C10—H10B108.4C16—C15—H15A108.3
C8—S1—C1091.98 (12)C14—C15—H15B108.3
O1—C7—N1125.0 (2)C16—C15—H15B108.3
O1—C7—C1120.7 (2)H15A—C15—H15B107.4
N1—C7—C1114.3 (2)C15—C14—C13117.1 (4)
C2—C1—C6119.0 (2)C15—C14—H14A108.0
C2—C1—C7122.1 (2)C13—C14—H14A108.0
C6—C1—C7118.9 (2)C15—C14—H14B108.0
N2—C11—C12113.0 (2)C13—C14—H14B108.0
N2—C11—H11A109.0H14A—C14—H14B107.3
C12—C11—H11A109.0C16—C17—C18116.8 (4)
N2—C11—H11B109.0C16—C17—H17A108.1
C12—C11—H11B109.0C18—C17—H17A108.1
H11A—C11—H11B107.8C16—C17—H17B108.1
C1—C2—C3120.5 (3)C18—C17—H17B108.1
C1—C2—H2119.7H17A—C17—H17B107.3
C3—C2—H2119.7C17—C16—C15118.6 (4)
C5—C6—C1120.5 (3)C17—C16—H16A107.7
C5—C6—H6119.7C15—C16—H16A107.7
C1—C6—H6119.7C17—C16—H16B107.7
C6—C5—C4120.2 (3)C15—C16—H16B107.7
C6—C5—H5119.9H16A—C16—H16B107.1
C4—C5—H5119.9C17—C18—H18A109.5
C5—C4—C3119.9 (3)C17—C18—H18B109.5
C5—C4—H4120.0H18A—C18—H18B109.5
C3—C4—H4120.0C17—C18—H18C109.5
C14—C13—C12115.2 (3)H18A—C18—H18C109.5
C14—C13—H13A108.5H18B—C18—H18C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.453.365 (4)168

Symmetry codes: (i) x−2, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5080).

References

  • Chandrakant, G. & Gaikwad, N. G. (2004). Bioorg. Med. Chem.12, 2151–2161. [PubMed]
  • Dwivedi, C., Gupta, T. K. & Parmar, S. S. (1972). J. Med. Chem.15, 553–554. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Oxford Diffraction (2008). CrysAlis PRO and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
  • Peng, Y.-Q., Song, G.-H. & Huang, F.-F. (2004). J. Chem. Res.10, 676–678.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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