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Volume 69 
Part 7 
Page o1036  
July 2013  

Received 16 March 2013
Accepted 27 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.055
wR = 0.115
Data-to-parameter ratio = 17.4
Details
Open access

3,3-Bis(methylsulfanyl)-1-(4-nitrophenyl)prop-2-en-1-one

aCollege of Chemistry and Chemical Engineering, Jiang Xi Normal University, Nanchang, Jiang Xi 330022, People's Republic of China, and bBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China
Correspondence e-mail: yucy@iccas.ac.cn

In the title compound, C11H11NO3S2, the S-Csp2 bonds are shorter [1.746 (3) and 1.750 (2) Å] than the S-CH3 bonds [1.794 (3) and 1.806 (3) Å], which we attribute to d-[pi] interactions between the S atoms and the C=C bond. The 1,1-bis(methylsulfanyl)-3-oxopropylene fragment and the 4-nitrophenyl group are both almost planar, with the largest deviations from their mean planes being 0.053 (1) and 0.017 (2) Å, respectively. The dihedral angle between the two planes is 35.07 (7)°. Molecules in the crystal are linked into a three-dimensional network by C-H...S and C-H...O hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Huang & Liu (1989[Huang, Z.-T. & Liu, Z.-R. (1989). Synth. Commun. 19, 943-958.]). For applications, see: Barun et al. (2000[Barun, H. O., Ila, H. & Junjappa, H. (2000). J. Org. Chem. 65, 1583-1587.]); Kuettel et al. (2007[Kuettel, S., Zambon, A., Kaiser, M., Brun, R., Scapozza, L. & Perozzo, R. (2007). J. Med. Chem. 50, 5833-5839.]). For general background on ketene aminals, see: Huang & Wang (1994[Huang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233-1262.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11NO3S2

  • Mr = 269.33

  • Triclinic, [P \overline 1]

  • a = 7.917 (2) Å

  • b = 8.739 (2) Å

  • c = 9.574 (3) Å

  • [alpha] = 70.415 (13)°

  • [beta] = 81.985 (14)°

  • [gamma] = 73.283 (13)°

  • V = 597.0 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.44 mm-1

  • T = 173 K

  • 0.27 × 0.24 × 0.05 mm

Data collection
  • Rigaku Saturn724+ CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku (2007). CrystalClear. Rigau Corporation, Tokyo, Japan.]) Tmin = 0.581, Tmax = 1.000

  • 7843 measured reflections

  • 2719 independent reflections

  • 2394 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.115

  • S = 1.15

  • 2719 reflections

  • 156 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 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
C11-H11...S2i 0.95 2.93 3.614 (3) 130
C8-H8...O3ii 0.95 2.63 3.204 (3) 119
C2-H2B...O3iii 0.98 2.68 3.297 (4) 122
C10-H10...O1iv 0.95 2.66 3.602 (3) 171
C1-H1C...O1v 0.98 2.59 3.551 (3) 167
C7-H7...O2vi 0.95 2.55 3.499 (3) 179
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+2, -z+1; (iii) -x+2, -y+1, -z+1; (iv) x-1, y, z; (v) x, y-1, z; (vi) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigau Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2092 ).


Acknowledgements

We thank Tongling Liang at the Chinese Academy of Sciences for the X-ray crystallographic structure determination.

References

Barun, H. O., Ila, H. & Junjappa, H. (2000). J. Org. Chem. 65, 1583-1587.  [CrossRef] [PubMed] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Huang, Z.-T. & Liu, Z.-R. (1989). Synth. Commun. 19, 943-958.  [CrossRef] [ChemPort] [Web of Science]
Huang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233-1262.  [CrossRef] [ChemPort]
Kuettel, S., Zambon, A., Kaiser, M., Brun, R., Scapozza, L. & Perozzo, R. (2007). J. Med. Chem. 50, 5833-5839.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Rigaku (2007). CrystalClear. Rigau Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1036  [ doi:10.1107/S1600536813014542 ]

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