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Volume 69 
Part 6 
Page o953  
June 2013  

Received 13 May 2013
Accepted 17 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.126
Data-to-parameter ratio = 18.5
Details
Open access

5-Isopropyl-5-methyl-2-sulfanylideneimidazolidin-4-one

aDivision of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
Correspondence e-mail: kunimoto@se.kanazawa-u.ac.jp

In the title compound, C7H12N2OS, the 2-sulfanylideneimidazolidin-4-one moiety is nearly planar, with a maximum deviation of 0.054 (2) Å. In the crystal, a pair of N-H...O hydrogen bonds and a pair of N-H...S hydrogen bonds each form a centrosymmetric ring with an R22(8) graph-set motif. The enantiomeric R and S molecules are alternately linked into a tape along [1-10] via these pairs of hydrogen bonds.

Related literature

For applications and the biological activity of 2-sulfanylideneimidazolidin-4-ones, see: Marton et al. (1993[Marton, J., Enisz, J., Hosztafi, S. & Timar, T. (1993). J. Agric. Food Chem. 41, 148-152.]). For the crystal structures of related compounds, see: Devillanova et al. (1987[Devillanova, F. A., Isaia, F., Verani, G., Battaglia, L. P. & Corradi, A. B. (1987). J. Chem. Res. 6, 192-193.]); Ogawa et al. (2009[Ogawa, T., Okumura, H., Honda, M., Suda, M., Fujinami, S., Kuwae, A., Hanai, K. & Kunimoto, K.-K. (2009). Anal. Sci. X-ray Struct. Anal. Online, 25, 91-92.]); Walker et al. (1969[Walker, L. A., Folting, K. & Merritt, L. L. (1969). Acta Cryst. B25, 88-93.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For hydrogen-bond motifs, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]). For the synthetic procedure, see: Wang et al. (2006[Wang, Z. D., Sheikh, S. O. & Zhang, Y. (2006). Molecules, 11, 739-750.]).

[Scheme 1]

Experimental

Crystal data
  • C7H12N2OS

  • Mr = 172.26

  • Monoclinic, P 21 /c

  • a = 5.8317 (5) Å

  • b = 9.2114 (8) Å

  • c = 16.8967 (16) Å

  • [beta] = 95.855 (3)°

  • V = 902.92 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 123 K

  • 0.20 × 0.10 × 0.04 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.795, Tmax = 0.988

  • 9484 measured reflections

  • 2051 independent reflections

  • 1660 reflections with F2 > 2[sigma](F2)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.126

  • S = 1.14

  • 2051 reflections

  • 111 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...S1i 0.78 (3) 2.63 (3) 3.383 (2) 162 (3)
N2-H2...O1ii 0.91 (4) 1.93 (4) 2.820 (3) 166 (3)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2006[Rigaku (2006). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2008 in Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5273 ).


References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.  [ISI] [CrossRef] [ChemPort] [details]
Devillanova, F. A., Isaia, F., Verani, G., Battaglia, L. P. & Corradi, A. B. (1987). J. Chem. Res. 6, 192-193.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Marton, J., Enisz, J., Hosztafi, S. & Timar, T. (1993). J. Agric. Food Chem. 41, 148-152.  [CrossRef] [ChemPort] [ISI]
Ogawa, T., Okumura, H., Honda, M., Suda, M., Fujinami, S., Kuwae, A., Hanai, K. & Kunimoto, K.-K. (2009). Anal. Sci. X-ray Struct. Anal. Online, 25, 91-92.  [CSD] [CrossRef] [ChemPort]
Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.
Rigaku (2006). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Walker, L. A., Folting, K. & Merritt, L. L. (1969). Acta Cryst. B25, 88-93.  [CrossRef] [ChemPort] [details]
Wang, Z. D., Sheikh, S. O. & Zhang, Y. (2006). Molecules, 11, 739-750.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o953  [ doi:10.1107/S1600536813013639 ]

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