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Volume 69 
Part 7 
Pages o1173-o1174  
July 2013  

Received 17 June 2013
Accepted 24 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.091
Data-to-parameter ratio = 15.3
Details
Open access

(2Z)-3-(2,4-Dichlorophenyl)-3-hydroxy-N-phenylprop-2-enethioamide

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India,bDepartment of Agrochemicals & Pest Management, Shivaji University, Kolhapur, India, and cDepartment of Chemistry, Shivaji University, Kolhapur, India
Correspondence e-mail: rkvk.paper11@gmail.com

In the title molecule, C15H11Cl2NOS, the dihedral angle between the phenyl and benzene rings is 72.24 (1)°. In the crystal, pairs of N-H...S hydrogen bonds form dimers with twofold rotational symmetry. The dimers are connected by weak C-H...O hydrogen bonds, forming a two-dimensional network parallel to (001). An intramolecular O-H...S hydrogen bond is also observed.

Related literature

For the biological activity and applications of thioamides, see: Zahid et al. (2009[Zahid, M., Yasin, K. A., Akhtar, T., Rama, N. H., Hameed, S., Al Masoudi, N. A., Loddo, R. & La Colla, P. (2009). Arkivoc, xi, 85-93.]); Jagodzinski (2003[Jagodzinski, T. S. (2003). Chem. Rev. 103, 197-227.]); Lebana et al. (2008[Lebana, S. T., Sultana, R. & Hendal, G. (2008). Polyhedron, 27, 1008-1016.]). For the synthesis of thioamides, see: Bauer & Kuhlein (1985[Bauer, W. & Kuhlein, K. (1985). Houben-Weyl Methoden der Organischen Chemie, Vol. E5, p. 1218. Stuttgart, New York: Georg Thieme Verlag.]); Cava & Levinson (1985[Cava, M. P. & Levinson, M. I. (1985). Tetrahedron, 41, 5061-5087.]). For the synthesis of the title compound, see: Rudrof et al. (1979[Rudrof, W. D., Schierhorn, A. & Augustin, M. (1979). Tetrahedron, 35, 551-556.]). For related structures, see: Xu et al. (2005[Xu, L.-Z., Yang, S.-H., Zhu, C.-Y., Li, K. & Liu, F.-Q. (2005). Acta Cryst. E61, o259-o260.]); Cowley et al. (2002[Cowley, A. R., Dilworth, J. R. & Dorinelly, P. S. (2002). J. Am. Chem. Soc. 124, 5270-5271.]); Jiang (2009[Jiang, J.-H. (2009). Acta Cryst. E65, o52.]); Patil et al. (2011[Patil, D. R., Salunkhe, S. M., Aitawade, M. M., Deshmukh, M. B., Kolekar, G. B. & Anbhule, P. V. (2011). Pharma Chem. 3, 207-214.]); Deshmukh et al. (2009[Deshmukh, M. B., Salunkhe, S. M., Patil, D. R. & Anbhule, P. V. (2009). Eur. J. Med. Chem. 44, 2651-2654.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11Cl2NOS

  • Mr = 324.21

  • Orthorhombic, P c c n

  • a = 28.9562 (6) Å

  • b = 13.2610 (3) Å

  • c = 7.5284 (2) Å

  • V = 2890.82 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.59 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.1 mm

Data collection
  • Agilent Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.835, Tmax = 1.000

  • 63107 measured reflections

  • 2836 independent reflections

  • 2275 reflections with I > 2[sigma](I)

  • Rint = 0.067

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.091

  • S = 1.11

  • 2836 reflections

  • 185 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...S1i 0.86 2.61 3.4397 (18) 162
C3'-H3'...O1ii 0.93 2.59 3.496 (3) 164
O1-H11...S1 0.89 (3) 2.10 (3) 2.9315 (18) 157 (2)
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5625 ).


Acknowledgements

RK is thankful to the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/ CMP-47/2003.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bauer, W. & Kuhlein, K. (1985). Houben-Weyl Methoden der Organischen Chemie, Vol. E5, p. 1218. Stuttgart, New York: Georg Thieme Verlag.
Cava, M. P. & Levinson, M. I. (1985). Tetrahedron, 41, 5061-5087.  [CrossRef] [ChemPort] [Web of Science]
Cowley, A. R., Dilworth, J. R. & Dorinelly, P. S. (2002). J. Am. Chem. Soc. 124, 5270-5271.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Deshmukh, M. B., Salunkhe, S. M., Patil, D. R. & Anbhule, P. V. (2009). Eur. J. Med. Chem. 44, 2651-2654.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jagodzinski, T. S. (2003). Chem. Rev. 103, 197-227.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Jiang, J.-H. (2009). Acta Cryst. E65, o52.  [CSD] [CrossRef] [IUCr Journals]
Lebana, S. T., Sultana, R. & Hendal, G. (2008). Polyhedron, 27, 1008-1016.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Patil, D. R., Salunkhe, S. M., Aitawade, M. M., Deshmukh, M. B., Kolekar, G. B. & Anbhule, P. V. (2011). Pharma Chem. 3, 207-214.  [ChemPort]
Rudrof, W. D., Schierhorn, A. & Augustin, M. (1979). Tetrahedron, 35, 551-556.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Xu, L.-Z., Yang, S.-H., Zhu, C.-Y., Li, K. & Liu, F.-Q. (2005). Acta Cryst. E61, o259-o260.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Zahid, M., Yasin, K. A., Akhtar, T., Rama, N. H., Hameed, S., Al Masoudi, N. A., Loddo, R. & La Colla, P. (2009). Arkivoc, xi, 85-93.  [CrossRef]


Acta Cryst (2013). E69, o1173-o1174   [ doi:10.1107/S1600536813017339 ]

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