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Volume 69 
Part 11 
Page o1699  
November 2013  

Received 15 October 2013
Accepted 17 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.082
Data-to-parameter ratio = 16.4
Details
Open access

1-Acetyl-5-(4-fluoro­phen­yl)-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, C11H9FN2O2S, the 2-sulfanylideneimidazolidin-4-one moiety is essentially planar, with a maximum deviation of 0.0183 (14) Å. The mean plane of this moiety is approximately coplanar with the attached acetyl group and perpendicular to the benzene ring, making dihedral angles of 9.70 (14) and 86.70 (6)°, respectively. In the crystal, mol­ecules are linked by N-H...O hydrogen bonds between the amide NH and acetyl C=O groups, forming a C(6) chain along the a-axis direction.

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: Casas et al. (1998[Casas, J. S., Castiñeiras, A., Couce, D., Playá, N., Sordo, J. & Varela, J. M. (1998). Acta Cryst. C54, 427-428.]); Sulbaran et al. (2007[Sulbaran, M. E., Delgado, G. E., Mora, A. J., Bahsas, A., Novoa de Armas, H. & Blaton, N. (2007). Acta Cryst. C63, o543-o545.]); Taniguchi et al. (2009[Taniguchi, K., Okumura, H., Honda, M., Suda, M., Fujinami, S., Kuwae, A., Hanai, K., Maeda, S. & Kunimoto, K.-K. (2009). Anal. Sci. X-ray Struct. Anal. Online, 25, 93-94.]). 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: Schlack & Kumpf (1926[Schlack, P. & Kumpf, W. (1926). Z. Physiol. Chem. 154, 125-170.]).

[Scheme 1]

Experimental

Crystal data
  • C11H9FN2O2S

  • Mr = 252.27

  • Monoclinic, P 21 /n

  • a = 7.1327 (9) Å

  • b = 23.852 (3) Å

  • c = 7.3437 (10) Å

  • [beta] = 113.541 (3)°

  • V = 1145.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 123 K

  • 0.30 × 0.10 × 0.08 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.829, Tmax = 0.977

  • 12234 measured reflections

  • 2612 independent reflections

  • 2418 reflections with F2 > 2[sigma](F2)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.082

  • S = 1.06

  • 2612 reflections

  • 159 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O2i 0.84 (2) 1.96 (2) 2.7836 (16) 167 (2)
Symmetry code: (i) x+1, y, z.

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: IS5315 ).


References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Casas, J. S., Castiñeiras, A., Couce, D., Playá, N., Sordo, J. & Varela, J. M. (1998). Acta Cryst. C54, 427-428.  [CSD] [CrossRef] [IUCr Journals]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Marton, J., Enisz, J., Hosztafi, S. & Timar, T. (1993). J. Agric. Food Chem. 41, 148-152.  [CrossRef] [ChemPort] [Web of Science]
Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.
Rigaku (2006). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Schlack, P. & Kumpf, W. (1926). Z. Physiol. Chem. 154, 125-170.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sulbaran, M. E., Delgado, G. E., Mora, A. J., Bahsas, A., Novoa de Armas, H. & Blaton, N. (2007). Acta Cryst. C63, o543-o545.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Taniguchi, K., Okumura, H., Honda, M., Suda, M., Fujinami, S., Kuwae, A., Hanai, K., Maeda, S. & Kunimoto, K.-K. (2009). Anal. Sci. X-ray Struct. Anal. Online, 25, 93-94.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1699  [ doi:10.1107/S1600536813028560 ]

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