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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2655.
Published online 2010 September 30. doi:  10.1107/S1600536810037256
PMCID: PMC2983327

1-Acetyl-5-isobutyl-2-sulfanylidene­imidazolidin-4-one

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C9H14N2O2S. In the crystal, the mol­ecules are linked by N—H(...)O hydrogen bonds, forming a chain along the a axis.

Related literature

For biological activity of thio­hydantoins, see: Lopez & Trigo (1985 [triangle]). For a related structure, see: Sulbaran et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2655-scheme1.jpg

Experimental

Crystal data

  • C9H14N2O2S
  • M r = 214.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2655-efi1.jpg
  • a = 7.1856 (8) Å
  • b = 9.7567 (11) Å
  • c = 16.4226 (15) Å
  • α = 101.231 (2)°
  • β = 93.965 (1)°
  • γ = 90.491 (1)°
  • V = 1126.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 298 K
  • 0.42 × 0.35 × 0.14 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.897, T max = 0.964
  • 5877 measured reflections
  • 3916 independent reflections
  • 2199 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.138
  • S = 1.02
  • 3916 reflections
  • 259 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; 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: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037256/is2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037256/is2592Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support bythe University Student Science and Technology Culture Foundation of Liaocheng University (No. SRT10056HX2).

supplementary crystallographic information

Comment

Thiohydantoins are known to exhibit a wide range of biological activities, including anticonvulsant, antiarrhythmic, anti-inflammatory, and antidiabetic properties, as well as herbicidal and fungicidal activity (Lopez & Trigo, 1985).

In the title compound (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the reported compound (Sulbaran et al., 2007). In the crystal structure, there exist intermolecular N—H···O hydrogen bonds (Table 1). The supramolecular chain structure along the a axis, which is built by weak intermolecular N—H···O hydrogen bonds.

Experimental

2-Amino-4-methylpentanoic acid (10 mmol) and NH4SCN (10 mmol) was dissolved in a 15 ml acetic anhydride and 2 ml acetic acid mixture and transferred in a round-bottom flask. The mixture was warmed, with agitation, to 373 K over a period of 1 h. The resulting solution was cooled in a ice/water mixture and stored in a freezer overnight. Crystal of (I) suitable for X-ray diffraction analysis were obtained by slow evaporation. Elemental analysis: calculated for C9H14N2O2S: C 50.45, H 6.59, N 13.07%; found: C 50.53, H 6.46, N 13.14%.

Refinement

All H atoms were placed in geometrically idealized positions (N—H 0.86 and C—H 0.96–0.97 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.

Crystal data

C9H14N2O2SZ = 4
Mr = 214.28F(000) = 456
Triclinic, P1Dx = 1.264 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1856 (8) ÅCell parameters from 1409 reflections
b = 9.7567 (11) Åθ = 2.5–22.5°
c = 16.4226 (15) ŵ = 0.27 mm1
α = 101.231 (2)°T = 298 K
β = 93.965 (1)°Block, colourless
γ = 90.491 (1)°0.42 × 0.35 × 0.14 mm
V = 1126.3 (2) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer3916 independent reflections
Radiation source: fine-focus sealed tube2199 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.897, Tmax = 0.964k = −9→11
5877 measured reflectionsl = −18→19

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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0539P)2 + 0.2948P] where P = (Fo2 + 2Fc2)/3
3916 reflections(Δ/σ)max = 0.001
259 parametersΔρmax = 0.27 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
N10.3760 (3)0.2881 (3)0.16750 (16)0.0404 (7)
N20.0770 (3)0.2612 (3)0.18054 (17)0.0523 (8)
H2−0.04170.27100.17460.063*
N30.0219 (3)0.7835 (3)0.17203 (16)0.0429 (7)
N40.3235 (4)0.7558 (3)0.18537 (17)0.0518 (8)
H40.44060.76640.18000.062*
O10.0752 (3)0.1110 (3)0.27212 (17)0.0746 (8)
O20.6815 (3)0.2536 (3)0.16880 (16)0.0638 (7)
O30.3503 (3)0.6072 (3)0.27747 (17)0.0748 (8)
O4−0.2837 (3)0.7469 (3)0.17042 (16)0.0649 (7)
S10.13550 (12)0.41653 (10)0.06933 (6)0.0563 (3)
S20.23535 (13)0.90538 (11)0.07109 (6)0.0626 (3)
C10.2002 (4)0.3238 (3)0.13812 (19)0.0403 (8)
C20.1575 (4)0.1820 (4)0.2329 (2)0.0520 (9)
C30.3646 (4)0.2041 (4)0.2328 (2)0.0466 (9)
H30.42430.11410.21580.056*
C40.4495 (5)0.2774 (4)0.3174 (2)0.0569 (10)
H4A0.57330.31210.31060.068*
H4B0.37470.35760.33730.068*
C50.4652 (6)0.1881 (4)0.3833 (2)0.0698 (11)
H50.33940.15430.39000.084*
C60.5376 (7)0.2777 (5)0.4657 (3)0.1015 (16)
H6A0.66420.30680.46210.152*
H6B0.53280.22450.50890.152*
H6C0.46160.35850.47820.152*
C70.5853 (8)0.0619 (5)0.3603 (3)0.121 (2)
H7A0.70660.09160.34860.182*
H7B0.52830.00070.31190.182*
H7C0.59720.01310.40580.182*
C80.5509 (4)0.3120 (3)0.1399 (2)0.0453 (8)
C90.5730 (5)0.4020 (4)0.0785 (2)0.0639 (11)
H9A0.70250.40900.06860.096*
H9B0.52770.49340.09960.096*
H9C0.50300.36210.02730.096*
C100.1898 (4)0.8166 (3)0.1424 (2)0.0427 (8)
C110.2580 (5)0.6769 (4)0.2376 (2)0.0502 (9)
C120.0504 (4)0.6996 (3)0.2371 (2)0.0461 (9)
H12−0.01750.60990.22020.055*
C13−0.0073 (5)0.7752 (4)0.3214 (2)0.0573 (10)
H13A0.07450.85640.34060.069*
H13B−0.13290.80860.31420.069*
C14−0.0024 (6)0.6886 (4)0.3882 (2)0.0724 (12)
H140.12550.65670.39550.087*
C15−0.1284 (9)0.5618 (6)0.3658 (3)0.126 (2)
H15A−0.12930.51550.41220.190*
H15B−0.08400.49920.31890.190*
H15C−0.25260.58940.35180.190*
C16−0.0487 (7)0.7818 (6)0.4705 (3)0.1089 (17)
H16A−0.17470.81270.46550.163*
H16B0.03520.86140.48310.163*
H16C−0.03550.72960.51430.163*
C17−0.1606 (4)0.8094 (4)0.1444 (2)0.0471 (9)
C18−0.2005 (5)0.9099 (4)0.0897 (2)0.0630 (10)
H18A−0.33300.91690.08000.094*
H18B−0.14660.87840.03760.094*
H18C−0.14780.99980.11570.094*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0242 (14)0.0472 (17)0.0518 (16)0.0029 (11)0.0067 (12)0.0132 (14)
N20.0207 (14)0.067 (2)0.074 (2)0.0038 (13)0.0043 (13)0.0246 (17)
N30.0261 (14)0.0508 (17)0.0527 (17)0.0051 (12)0.0052 (12)0.0115 (15)
N40.0248 (15)0.0608 (19)0.074 (2)0.0033 (13)0.0075 (14)0.0212 (17)
O10.0495 (16)0.092 (2)0.094 (2)−0.0114 (14)0.0122 (14)0.0441 (18)
O20.0275 (13)0.0854 (19)0.0865 (18)0.0089 (12)0.0085 (12)0.0342 (16)
O30.0490 (16)0.089 (2)0.098 (2)0.0208 (14)0.0066 (14)0.0459 (18)
O40.0317 (13)0.0777 (18)0.0915 (19)0.0010 (12)0.0099 (13)0.0299 (16)
S10.0400 (5)0.0709 (7)0.0607 (6)0.0080 (4)−0.0020 (4)0.0209 (5)
S20.0469 (6)0.0798 (8)0.0682 (7)0.0025 (5)0.0149 (5)0.0280 (6)
C10.0262 (17)0.044 (2)0.048 (2)0.0048 (14)0.0041 (14)0.0028 (17)
C20.0330 (19)0.062 (2)0.065 (2)−0.0020 (17)0.0063 (17)0.020 (2)
C30.0324 (18)0.051 (2)0.060 (2)0.0032 (15)0.0030 (16)0.0207 (19)
C40.044 (2)0.064 (2)0.064 (2)−0.0014 (18)0.0012 (18)0.019 (2)
C50.064 (3)0.085 (3)0.064 (3)−0.005 (2)−0.001 (2)0.026 (2)
C60.104 (4)0.130 (4)0.068 (3)−0.016 (3)−0.008 (3)0.021 (3)
C70.152 (5)0.109 (4)0.106 (4)0.043 (4)−0.021 (4)0.037 (4)
C80.0260 (18)0.051 (2)0.060 (2)0.0049 (15)0.0078 (16)0.0102 (19)
C90.042 (2)0.073 (3)0.085 (3)0.0027 (19)0.0208 (19)0.031 (2)
C100.0293 (18)0.045 (2)0.052 (2)0.0036 (15)0.0036 (15)0.0055 (17)
C110.036 (2)0.055 (2)0.062 (2)0.0085 (17)0.0075 (17)0.016 (2)
C120.0333 (18)0.049 (2)0.058 (2)0.0047 (15)0.0077 (16)0.0141 (19)
C130.049 (2)0.064 (2)0.062 (2)0.0079 (18)0.0116 (18)0.016 (2)
C140.067 (3)0.085 (3)0.072 (3)0.008 (2)0.011 (2)0.028 (3)
C150.173 (6)0.110 (4)0.108 (4)−0.037 (4)0.031 (4)0.044 (4)
C160.115 (4)0.143 (5)0.070 (3)0.022 (4)0.023 (3)0.020 (3)
C170.0322 (19)0.051 (2)0.058 (2)0.0043 (16)0.0054 (16)0.0091 (19)
C180.040 (2)0.072 (3)0.079 (3)0.0074 (18)−0.0009 (19)0.023 (2)

Geometric parameters (Å, °)

N1—C11.393 (4)C6—H6B0.9600
N1—C81.398 (4)C6—H6C0.9600
N1—C31.478 (4)C7—H7A0.9600
N2—C21.368 (4)C7—H7B0.9600
N2—C11.372 (4)C7—H7C0.9600
N2—H20.8600C8—C91.476 (5)
N3—C101.390 (4)C9—H9A0.9600
N3—C171.399 (4)C9—H9B0.9600
N3—C121.472 (4)C9—H9C0.9600
N4—C101.361 (4)C11—C121.510 (4)
N4—C111.363 (4)C12—C131.524 (4)
N4—H40.8600C12—H120.9800
O1—C21.209 (4)C13—C141.508 (5)
O2—C81.218 (4)C13—H13A0.9700
O3—C111.205 (4)C13—H13B0.9700
O4—C171.217 (4)C14—C151.497 (6)
S1—C11.626 (3)C14—C161.534 (5)
S2—C101.635 (3)C14—H140.9800
C2—C31.502 (4)C15—H15A0.9600
C3—C41.517 (5)C15—H15B0.9600
C3—H30.9800C15—H15C0.9600
C4—C51.515 (5)C16—H16A0.9600
C4—H4A0.9700C16—H16B0.9600
C4—H4B0.9700C16—H16C0.9600
C5—C71.512 (6)C17—C181.471 (5)
C5—C61.517 (5)C18—H18A0.9600
C5—H50.9800C18—H18B0.9600
C6—H6A0.9600C18—H18C0.9600
C1—N1—C8129.4 (3)C8—C9—H9A109.5
C1—N1—C3111.9 (2)C8—C9—H9B109.5
C8—N1—C3118.6 (3)H9A—C9—H9B109.5
C2—N2—C1114.9 (3)C8—C9—H9C109.5
C2—N2—H2122.6H9A—C9—H9C109.5
C1—N2—H2122.6H9B—C9—H9C109.5
C10—N3—C17129.3 (3)N4—C10—N3105.3 (3)
C10—N3—C12111.7 (2)N4—C10—S2123.4 (2)
C17—N3—C12118.8 (3)N3—C10—S2131.3 (3)
C10—N4—C11115.1 (3)O3—C11—N4126.2 (3)
C10—N4—H4122.5O3—C11—C12127.9 (3)
C11—N4—H4122.5N4—C11—C12105.9 (3)
N2—C1—N1104.9 (3)N3—C12—C11101.5 (3)
N2—C1—S1123.4 (2)N3—C12—C13112.7 (3)
N1—C1—S1131.7 (2)C11—C12—C13112.0 (3)
O1—C2—N2125.9 (3)N3—C12—H12110.1
O1—C2—C3127.8 (3)C11—C12—H12110.1
N2—C2—C3106.3 (3)C13—C12—H12110.1
N1—C3—C2101.6 (2)C14—C13—C12115.1 (3)
N1—C3—C4113.5 (3)C14—C13—H13A108.5
C2—C3—C4111.9 (3)C12—C13—H13A108.5
N1—C3—H3109.9C14—C13—H13B108.5
C2—C3—H3109.9C12—C13—H13B108.5
C4—C3—H3109.9H13A—C13—H13B107.5
C5—C4—C3115.3 (3)C15—C14—C13112.9 (4)
C5—C4—H4A108.5C15—C14—C16111.7 (4)
C3—C4—H4A108.5C13—C14—C16108.9 (4)
C5—C4—H4B108.5C15—C14—H14107.7
C3—C4—H4B108.5C13—C14—H14107.7
H4A—C4—H4B107.5C16—C14—H14107.7
C7—C5—C4113.2 (4)C14—C15—H15A109.5
C7—C5—C6110.9 (4)C14—C15—H15B109.5
C4—C5—C6109.3 (3)H15A—C15—H15B109.5
C7—C5—H5107.7C14—C15—H15C109.5
C4—C5—H5107.7H15A—C15—H15C109.5
C6—C5—H5107.7H15B—C15—H15C109.5
C5—C6—H6A109.5C14—C16—H16A109.5
C5—C6—H6B109.5C14—C16—H16B109.5
H6A—C6—H6B109.5H16A—C16—H16B109.5
C5—C6—H6C109.5C14—C16—H16C109.5
H6A—C6—H6C109.5H16A—C16—H16C109.5
H6B—C6—H6C109.5H16B—C16—H16C109.5
C5—C7—H7A109.5O4—C17—N3115.9 (3)
C5—C7—H7B109.5O4—C17—C18122.3 (3)
H7A—C7—H7B109.5N3—C17—C18121.7 (3)
C5—C7—H7C109.5C17—C18—H18A109.5
H7A—C7—H7C109.5C17—C18—H18B109.5
H7B—C7—H7C109.5H18A—C18—H18B109.5
O2—C8—N1116.2 (3)C17—C18—H18C109.5
O2—C8—C9122.6 (3)H18A—C18—H18C109.5
N1—C8—C9121.1 (3)H18B—C18—H18C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.861.992.834 (3)167
N4—H4···O4ii0.862.012.850 (3)167

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2592).

References

  • Lopez, C. A. & Trigo, G. G. (1985). Adv. Heterocycl. Chem.38, 177–179.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Sulbaran, M. E., Delgado, G. E., Mora, A. J., Bahsas, A., Novoa de Armas, H. & Blaton, N. (2007). Acta Cryst. C63, o543–o545. [PubMed]

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